PATENT DOCUMENT

Abstract:
A monoazo reactive red dyestuff of the formula (I), 
     wherein the R 1 , R 2 , R 3 , X, D, Z and n are as defined in the description. These kinds of dyestuffs are suitable for dyeing and printing of materials containing either cellulose fibers, such as cotton, artificial cotton, linen, and artificial linen, or synthetic polyamide, such as wool, silk, and nylon etc., as well as on mixed or cross-linked cellulose fibers and other fibers. Dyed materials with excellent properties can be obtained, showing especially outstanding performance in of wash-off, level-dyeing, light fastness and perspiration-light fastness.

Full Description:
BACKGROUND OF THE INVENTION 
     1. Field of the Invention 
     The invention relates to the technical field of the fiber-reactive dyes, in particular relates to a novel monoazo reactive red dyestuff. 
     2. Description of Related Art 
     The practice of dyeing with fiber-reactive dyes has led to heightened expectations of the quality of the dyeings. Consequently there continues to be a demand for novel fiber-reactive dyes that have improved properties. Especially in demand are red reactive dyes having high fastness properties. It is true that British Patent No. 836,248, U.S. Pat. No. 2,979,498 and European Patent Application Publication No. 0 070 806 disclose numerous red fiber-reactive dyes, but the fastness properties of the dyeings obtainable with these dyes, especially the lightfastness and the perspiration lightfastness, are in need of improvement. 
     U.S. Pat. No. 5,227,475 discloses fiber-reactive dyestuffs having the following formula:                           
     The practice of dyeing using reactive dyestuffs has improved the quality of the dyeings and the efficiency of the dyeing process. Reactive dyestuffs generally display good dyeing and fastness properties but the light fastness, alone and in presence of perspiration, of red fiber-reactive dyestuffs is generally only modest and in need of improvement. 
     SUMMARY OF THE INVENTION 
     The present invention provides novel azo compounds having improved properties in this respect and are azo derivatives which compounds conform to the formula (I), 
     wherein: 
     X is —NHCN, —OH, —SCH2COOH, —NHSO2CH3, 3-carboxypyridinium,                           
     halogen; preferably X is —NHCN, 3-carboxypyridinium or halogen, wherein the halogen is preferably fluorine or chlorine; 
     D is a phenyl or naphthyl group having 0 to 3 substituent groups, said substituent groups are selected from the groups consisting of halogen, C 1-4  alkyl, C 1-4  alkoxyl, nitro, amino, hydroxyl, carboxyl, phosphonic acid and sulfo group; preferably D is phenyl having 0 to 3 substituent groups; 
     Z is —SO 2 —CH═CH 2  or SO 2 —CH 2 —CH 2 —U; U is —OSO 3 H, Cl, Br, —OPO 3 H 2 , —SSO 3 H or                           
     preferably Z is —SO 2 CH═CH 2    
     or —SO 2 —CH 2 —CH 2 —OSO 3 H; 
     R 2  is sulfo, carboxy, halogen or C 1-4  alkoxy; preferably R 2  is sulfo or carboxy; 
     n is 0 or 1, and preferably n is 1; 
     when X is a halogen atom, R 1  is limited to a hydrogen atom and R 3  is limited to C 1-4  alkyl or C 1-4  alkyl having at least one substituent; preferably when X is fluorine atom or chlorine atom, R 1  is hydrogen atom and R 3  is C 1-4  alkyl; 
     when X is —NHCN, —OH, —SCH 2 COOH, —NHSO 2 CH 3 , 3-carboxypyridinium or                           
     R 1  and R 3  independently can be any group selected from hydrogen atom, C 1-4  alkyl, phenyl,                           
     or C 1-4  alkyl having one or more substituent group selected from hydroxyl, carboxyl, sulfo, carbamoyl or methoxy carbonyl; preferably R 1  and R 3  is hydrogen atom or C 1-4  alkyl. 
     The dyestuffs of the present invention is preferably represented by the following formula (Ia),                           
     wherein: 
     X is —NHCN, —OH, —SCH 2 COOH, —NHSO 2 CH 3 , 3-carboxypyridinium,                           
     halogen; preferably X is —NHCN, 3-carboxypyridinium fluorine or chlorine; 
     D is a phenyl or naphthyl having 0 to 3 substituent groups, said substituent groups are selected from the group consisting of halogen, C 1-4  alkyl, C 1-4  alkoxyl, nitro, amino, hydroxyl, carboxyl, phosphonic acid and sulfo group; 
     preferably D is phenyl having 0 to 3 substituent groups; 
     Z is —SO 2 —CH═CH 2  or SO 2 —CH 2 —CH 2 —U; U is —OSO 3 H, Cl, Br, —OPO 3 H 2 , —SSO 3 H or                           
     preferably Z is —SO 2 CH═CH 2    
     or —SO 2 —CH 2 —CH 2 —OSO 3 H; 
     n is 0 or 1, and preferably n is 1; 
     when X is a halogen atom, R1 is limited to a hydrogen atom and R 3  is limited to C 1-4  alkyl or C 1-4  alkyl having at least one substituent; preferably when X is fluorine atom or chlorine atom, R 1  is hydrogen atom and R 3  is C 1-4  alkyl; 
     when X is —NHCN, —OH, —SCH 2 COOH, —NHSO 2 CH 3 , 3-carboxypyridinium or                           
     R 1  and R 3  independently can be any group selected from hydrogen atom, C 1-4  alkyl, phenyl,                           
     or C 1-4  alkyl having one or more substituent group selected from hydroxyl, carboxyl, sulfo, carbamoyl or methoxy carbonyl; preferably R 1  and R 3  is hydrogen atom or C 1-4  alkyl. 
     The formula (I) dyestuff of the present invention is also preferably represented by the following formula (Ib),                           
     wherein: 
     X is —NHCN, —OH, —SCH 2 COOH, —NHSO 2 CH 3 , 3-carboxypyridinium,                           
     halogen; preferably X is —NHCN, 3-carboxypyridinium, chlorine or fluorine; 
     Z is —SO 2 —CH═CH 2  or SO 2 —CH 2 —CH 2 —U ; U is —OSO 3 H, Cl or Br; preferably Z is —SO 2 —CH 2 —CH 2 —OSO 3 H; 
     n is 0 or 1, and preferably n is 1; 
     when X is a chlorine atom or fluorine atom, R 1  is limited to a hydrogen atom and R 3  is limited to C 1-4  alkyl; preferably R 1  is hydrogen atom and R 3  is methyl or ethyl; 
     when X is —NHCN, —OH, —SCH 2 COOH, —NHSO 2 CH 3 , 3-carboxypyridinium or                           
     R 1  and R 3  independently can be any group selected from hydrogen atom, C 1-4  alkyl, or C 1-4  alkyl having one or more substituent group selected from hydroxyl, carboxyl, sulfo, carbamoyl or methoxy carbonyl; 
     preferably when X is fluorine atom or chlorine atom, R 1  and R 3  is hydrogen atom, methyl, or ethyl. 
     The formula (Ib) dyestuff is preferably the following formula (I-1) dyestuff:                           
     The formula (Ib) dyestuff is preferably the following formula (I-2) dyestuff:                           
     The formula (Ib) dyestuff is preferably the following formula (I-3) dyestuff:                           
     The formula (Ib) dyestuff is preferably the following formula (I-4) dyestuff:                           
     The formula (Ib) dyestuff is preferably the following formula (I-1) dyestuff:                           
     The formula (Ib) dyestuff is preferably the following formula (I-6) dyestuff                           
     These kinds of dyestuffs are suitable for dyeing of materials containing either cellulose fibers, such as cotton, synthetic cotton, hemp, and synthetic hemp, or synthetic polyamide and polyurethane fibers, such as wool, silk, and nylon. Dyed materials with excellent properties can be obtained, showing especially outstanding performance in light fastness. 
     Other objects, advantages, and novel features of the invention will become more apparent from the following detailed description when taken in conjunction with the accompanying drawings. 
    
    
     DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT 
     Dyestuffs (I) of the present invention can be synthesized by the following reaction sequence step (a) to step (c). 
     Step (a): 
     The compound of the formula (III) is reacted with 1,3,5-trihalogen triazine of formula (IV) to obtain the following compound of formula (V),                           
     wherein Hal is —F, —Cl, —Br; R 1 , R 2 , and n are defined as above formula (I). The reaction is carried out in aqueous solution at a temperature between 0 to 30° C., and below 20° C. is preferred. The acid generated in the reaction is neutralized by adding an acid-binding agent, and the pH is controlled between 3 to 7. Upon completion of the reaction, the product of formula (V) is obtained. 
     Step (b): 
     If while the X is not halogen, the compound of formula (V) is reacted with the compound of formula (VI) to obtain compound of formula (VII),                           
     wherein Hal is —F, —Cl, —Br; X is —NHCN, —OH, —SCH 2 COOH, —NHSO 2 CH 3 , 3-carboxypyridinium,                           
     R 1 , R 2 , and n are defined as for formula (I) above. The reaction temperature is controlled between 20 and 80° C., 40 to 60° C. is preferred. The acid generated in the reaction is neutralized by adding an acid binding agent. The pH is controlled between 4 and 12, and 6 to 10 is preferred. Upon completion the product of formula (VII) is obtained. 
     Step (c): 
     After the above reaction is completed, the compound of formula (VIII),                           
     wherein R 3 , D, and Z are defined as above, is then added to the solution of the compound of formula (VII). IF X is halogen, the compound of formula (VIII) wherein R 3 , D, and Z are defined as the above, is then added to the solution of the compound of formula (V). The reaction temperature is controlled between 30 to 100° C., and 55 to 85° C. is preferred. The acid generated in the reaction is neutralized by adding an acid binding agent. The pH is controlled between 3 to 11, 3 to 7 is preferred. Upon completion of the reaction, dyestuffs represented by formula (I) are obtained. 
     In the above reaction steps (a) to (c), the compounds of formula (III) and (IV) and (VI) and (VIII) can be reacted with one another in any sequence to yield the derivatives represented by formula (I). 
     The preparation of the compound of formula (III) is described in U.S. Pat. No. 4,837,310. 
     Compound (III) can be produced from a nitro compound of formula (X), which is diazotized at −10 to 20° C. in conventional manner, followed by coupling with a naphthol of formula (XI) at a temperature of −10 to 50° C., preferably 0 to 30° C., while controlling the pH within a range of 1 to 7, preferably 1 to 5. The resulting compound (XII) obtained is then reduced at a temperature of 40 to 100° C. in the presence of sodium sulfide. According to any one of the above sequences, the monoazo naphthol compound of the formula (III) can be obtained.                           
     Examples of compounds of formula (X) include: 
     2-methoxy-4-nitroaniline, 2-ethoxy-4-nitroaniline, 2-propoxy-4-nitroaniline, 2-butoxy-4-nitroaniline, 4-nitroaniline-2-sulfonic acid, 2-carboxy-4-nitroaniline, 2-fluoro-4-nitroaniline, 2-chloro-4-nitroaniline, 2-bromo-4-nitroaniline. 
     Examples of the compounds of formula (XI) are:                         
                         
                           
     The above compounds of formula (VIII) can be synthesised by reacting the compound of formula (XIII) with an alkylating agent. 
     
       
         H 2 N—D—Z  (XIII) 
       
     
     Examples of the alkylation reagents are: alkylhalide, dialkylsulfate, monosubstituted ethylene, or alkene oxide. 
     Examples of the alkylhalide are: 
     methylchloride, ethylchloride, n-propylchloride, isopropylchloride, n-butylchloride, isobutylchloride, sec-butylchloride, methylbromide, ethylbromide, n-propylbromide, isopropylbromide, n-butylbromide, isobutylbromide, sec-butylbromide. 
     Examples of the dialkylsulfate are: dimethylsulfate, diethylsulfate, dipropylsulfate. Examples of the monosubstituted ethylene are: acrylonitrile, acrylic acid, methylacrylate, ethylacrylate, acrylamide, vinylsulfonic acid. Examples of the alkene oxide are: ethyleneoxide, propyleneoxide, glycol, trimethyleneoxide, β-buthyloxide, 2-methyl-α-buthyleneoxide, 2-ethyl-3 -methyleneoxide, methoxyethyleneoxide, or n-buthoxyleneoxide. 
     Examples of compound of formula (XIII) are: 
     1-aminobenzene-3-β-sulfatoethylsulfone, 
     1-aminobenzene-4-β-sulfatoethylsulfone, 
     1-aminobenzene-3 -phosphatoethylbenzene, 
     1-amino-4-methylbenzene-3-β-sulfatoethylsulfone, 
     1-aminobenzene-3-β-chloroethylsulfone, 
     1-amino-4-methoxybenzene-3-β-sulfatoethylsulfone, 
     1-amino-2,5-dimethylbenzene-4-β-sulfatoethylsulfone, 
     1-amino-2-methoxybenzene-4-β-sulfatoethylsulfone, 
     1-amino-2-chlorobenzene-4-β-sulfatoethylsulfone, 
     1-amino-4-methoxybebzene-5-β-sulfatoethylsulfone, 
     2-aminonaphthalene-8-β-sulfatoethylsulfone-6-sulfonic acid, 
     2-aminonaphthalene-8-β-sulfatoethylsulfone, 
     1-amino-2,5-dimethoxybenzene-4-vinylsulfone, 
     1-amino-2-methoxy-5-methylbenzene-4-β-sulfatoethylsulfone, 
     2-aminonaphthalene-4,5,6-β-sulfatoethylsulfone, 
     2-aminonaphthalene-4,5,7-β-sulfatoethylsulfone, 
     1-amino-2-bromobenzene-4-vinylsulfone, 
     2-amino-8-sulfonaphthalene-6-β-sulfatoethylsulfone, 
     2-aminonaphthalene-8-β-phhosphatoethylsulfone-6-sulfonic acid, 
     2-aminonaphthalene-8-vinylsulfone-6-sulfonic acid, 
     1-amino-2-methoxy-5-methylbenzene-4-μ-chloroethylsulfone, 
     1-aminobenzene-2,3-vinylsulfone, 1-aminobenzene-2,4-vinylsulfone, 
     1-amino-2-methoxy-5-chlorobenzene-4-β-chloroethylsulfone, 
     1-amino-2-methoxy-5-chlorobenzene-4-vinylsulfone, 
     1-amino-2-ethoxy-5-chlorobenzene-4-β-chloroethylsulfone, 
     1-amino-2-ethoxy-5-chlorobenzene-4-vinylsulfone, 
     2-aminonaphthalene-8-β-sulfatoethylsulfone-1-sulfonic acid, 
     5-chloroaniline-2-β-sulfatoethylsulfone, 
     5-sulfoaniline-2-β-sulfatoethylsulfone, aniline-2-β-phosphatoethylsulfone, 
     5-chloroaniline-2-β-phosphatoethylsulfone, 5-chloroaniline-2-vinylsulfone, 
     5-sulfoaniline-2-vinylsulfone, aniline-2-β-chloroethylsulfone, 
     5-chloroaniline-2-β-chloroethylsulfone, 
     5-sulfoaniline-2-β-chloroethylsulfone, aniline-2-β-thiosulfatoethylsulfone, 
     5-chloroaniline-2-β-thiosulfatoethylsulfone, 
     5-sulfoaniline-2-β-thiosulfatoethylsulfone, 
     3-Amino-2′-(2-sulfatoethylsulfonyl)ethylbenzamide, 
     4-Amino-2′-(2-sulfatoethylsulfonyl)ethylbenzamide. 
     The dyestuffs of the present invention can be produced by the above methods, reaction conditions are fully described in the above description. The dyestuffs of the present invention can be purified by known processes such as spray drying, precipitation, or filtration. They can be in the form of powder, granules, particle or liquid and an auxiliary reagent, for example, retarding agent, leveling agent, assistant agent, surfactant agent, or dispersing agent may be added. 
     The dyestuffs of the present invention all contain at least one anionic group, such as a sulfonic acid group. For convenience they are expressed as free acid in the specification. When the dyestuffs of the present invention are manufactured, purified or used, they often exist in the form of water soluble salts, especially the alkaline metal salts, such as the sodium salt, lithium salt, potassium salt or ammonium salt, preferably sodium salt. 
     The dyestuffs of formula (I) in accordance with the present invention are fiber-reactive and useful for dyeing or printing hydroxyl group-containing and amide group-containing materials. 
     The dyestuffs of formula (I) according to the invention are suitable for dyeing and printing the various materials, such as silk, leather, wool, polyamide fibers and polyurethanes, and in particular all types of fiber materials containing cellulose. Examples of such fiber materials are the natural cellulose fibers, such as cotton, linen and hemp, as well as cellulose and regenerated cellulose. The dyestuffs of formula (I) are also suitable for dyeing or printing fibers which contain hydroxy groups and are contained in blended fabrics, for example mixtures of cotton with polyester fibers or polyamide fibers. 
     The dyestuffs according to the invention can be applied to the fiber material and fixed on the fiber in various ways, in particular in the form of aqueous dyestuff solutions and printing pastes. They are suitable both for the exhaust dyeing and for dyeing by the pad-dyeing process, in which the goods are impregnated with aqueous dyestuff solutions, if appropriate containing salts, and the dyestuff is fixed, after an alkali treatment or in the presence of alkali, if appropriate under the action of heat. The dyestuffs according to the invention are particularly suitable for the so-called cold pad-batch process, in which the dyestuff is applied to the padder together with the alkali and is then fixed by storage at room temperature for several hours. After fixing, the dyeings or prints are rinsed thoroughly with cold and hot water, if appropriate with addition of a dispersing agent which promotes diffusion of the non-fixed dye residues. 
     The present invention therefore also relates to the use of the compounds of the formula (I) according to the invention for dyeing (including printing) these materials and to processes for dyeing (and printing) such materials by a procedure which is customary per se, in which a compound of the formula (I) is employed as the coloring agent, by applying the compound of formula (I) to the material in an aqueous medium and fixing it on the material by means of heat or by means of an alkali or by means of both. 
     The dyestuffs of formula (I) are distinguished by a high reactivity, good fixing capacity and very good build-up capacity. The dyestuffs of the formula (I) can also exhibit excellent color-depth, level-dyeing and wash-off properties and high solubility as well as high exhaustion and fixation percentages. They can therefore be employed by the exhaust dyeing process at low dyeing temperatures and require only short steaming times in the pad-steam process. The degrees of fixing are high and the non-fixed portions can easily be washed out, the difference between the degree of exhaustion and the degree of fixing being remarkably small, i.e. the soaping loss is very low. The dyestuffs of formula (I) are also particularly suitable for printing, above all on cotton, and similarly also for printing nitrogen-containing fibers, for example wool or silk or blended fabrics which contain wool or silk. 
     The dyeings and prints produced on cellulose fiber materials with the dyestuffs according to the invention have a good depth of color and a high fiber-dyestuff bonding stability both in the acid and in the alkaline range, and furthermore good light-fastness, good perspiration-light fastness and very good wet-fastness properties, such as fastnesses to washing, water, seawater, cross-dyeing and perspiration, as well as a good fastness to pleating, fastness to ironing and fastness to rubbing. 
     The Examples that follow serve to illustrate the invention, which are only illustrative, but not limiting. The compounds are depicted in the formulae are shown in the form of free acids; in general, they are prepared and isolated in the form of their alkali metal salts and used for dyeing in the form of their salts. In the same way it is possible to use the starting compounds and components mentioned in the form of free acids in the examples below in particular the Table of examples, in the synthesis as such or in the form of their salts, preferably alkali metal salts. 
     The Examples that follow serve to illustrate the invention. Parts and percentages are by weight, unless otherwise stated. Parts by weight bear the same relation to parts by volume as the kilogram to the liter. 
     The absorption maxima (λ max) in the visible region reported for the compounds according to the present invention were determined from aqueous solutions of alkali metal salts. 
     EXAMPLE 1 
     A solution containing 4-nitroaniline-2-sulfonic acid (21.8 parts) and a 35% aqueous solution of sodium nitrite (21.7 parts) in water (150 parts) was introduced into a solution containing ice water (300 parts) and concentrated hydrochloric acid (35.5 parts), while controlling the temperature at 0 to 5° C., and the mixture was stirred for 1 hour at this temperature to effect diazotization. 
     Successively, after excess nitrous acid had been decomposed, 2-amino-8-hydroxynaphthalene-3,6-disulfonic acid (31.9 parts) was added to the reaction mixture, and the mixture was stirred for 12 hours at room temperature, thereby performing a coupling reaction. Thereafter, the reaction mixture was adjusted to pH 8 to 10, and mixed with sodium sulfide (10.7 parts), and the mixture was heated to 60° C. and stirred for 3 hours at this temperature to effect reduction of the nitro group. Then, the reaction mixture was mixed with sodium chloride (40 parts) to deposit crystals, which were collected on a filter and washed. The resulting wet cake was dissolved in water (400 parts). The solution was mixed with cyanuric chloride (16.7 parts), and the mixture was stirred for 5 hours at 0 to 10° C., while controlling the pH within a range of 4 to 5 using a 20% aqueous solution of sodium carbonate, thereby performing a first condensation compound of formula (1).                           
     EXAMPLE 2 
     To a solution containing the compound of Example 1 was added 27.8 parts of 1-N-ethylaminobenzene-3-β-sulfatoethylsulfone. The mixture was heated to 55° C., and was maintained at pH 4 to 5 for 5 hours. 
     To the resulting solution was added sodium chloride to precipitate the desired product of formula (2), (λmax=525 nm),                           
     EXAMPLE 3 to 33 
     The procedure described in Example 2 is repeated, reacting the compound of Example 1 with the following compounds, 3 to 33. As a result, bluish red (525±2 nm) monoazo derivatives are obtained. 
     EXAMPLE 
     No. Compound Used 
     3 1-N-ethylaminobenzene-4-β-sulfatoethylsulfone 
     4 1-N-ethylaminobenzene-2-β-sulfatoethylsulfone 
     5 1-N-ethylamino-4-methoxybenzene-3-β-sulfatoethylsulfone 
     6 1-N-methylaminobenzene-3-β-sulfatoethylsulfone 
     7 1-N-methylaminobenzene-4-β-sulfatoethylsulfone 
     8 1-N-methylaminobenzene-2-β-sulfatoethylsulfone 
     9 1-N-methylamino-4-methoxybenzene-3-β-sulfatoethylsulfone 
     10 1-N-β-carbamoylethylaminobenzene-3-β-sulfatoethylsulfone 
     11 1-N-β-carbamoylethylaminobenzene-4-β-sulfatoethylsulfone 
     12 1-N-β-carbamoylethylaminobenzene-2-β-sulfatoethylsulfone 
     13 1-N-β-carbamoylmethylamino-4-methoxybenzene-3-β-sulfatoethylsulfone 
     14 1-N-n-propylaminobenzene-3-β-sulfatoethylsulfone 
     15 1-N-n-propylaminobenzene-4-β-sulfatoethylsulfone 
     16 1-N-n-propylaminobenzene-2-β-sulfatoethylsulfone 
     17 1-N-n-propylamino-4-methoxybenzene-3-β-sulfatoethylsulfone 
     18 1-N-β-cyanoethylaminobenzene-3-β-sulfatoethylsulfone 
     19 1-N-β-cyanoethylaminobenzene-4-β-sulfatoethylsulfone 
     20 1-N-β-cyanoethylaminobenzene-2-β-sulfatoethylsulfone 
     21 1-N-β-cyanoethylamino-4-methoxybenzene-3-β-sulfatoethylsulfone 
     22 1-N-β-hydroxyethylaminobenzene-3-β-sulfatoethylsulfone 
     23 1-N-β-hydroxyethylaminobenzene-4-β-sulfatoethylsulfone 
     24 1-N-β-hydroxyethylaminobenzene-2-β-sulfatoethylsulfone 
     25 1-N-β-hydroxyethylamino-4-methoxybenzene-3-β-sulfatoethylsulfone 
     26 1-N-β-sulfatoethylaminobenzene-3-β-sulfatoethylsulfone 
     27 1-N-β-methoxycarbonylethylaminobenzene-3-β-sulfatoethylsulfone 
     28 1-N-ethylamino-2-methoxybenzene-5-β-sulfatoethylsulfone 
     29 1-N-ethylamino-2,4-dimethylbenzene-5-β-sulfatoethylsulfone 
     30 1-N-ethylamino-2-methoxy-5-methylbenzene-3-β-sulfatoethylsulfone 
     31 1-N-ethylaminonaphthalene-6-β-sulfatoethylsulfone 
     32 1-N-ethylamino-8-sulfonaphthalene-6-β-sulfatoethylsulfone 
     33 1-N-methylaminonaphthalene-8-β-sulfatoethylsulfone 
     EXAMPLE 34 
     To a solution containing the compound of Example 1 was added an aqueous solution of 3.78 parts of cyanamide in about 100 parts of water, and the mixture is heated to 40˜60° C. and maintained at a pH 8 to 10 by means of a 20% aqueous solution of sodium carbonate until the reaction has ended, after 6 to 7 hours to give the monochlorotriazine of formula (34):                           
     EXAMPLE 35 
     To a solution containing the product of Example 34 are added 25.3 parts of 1-aminobenzeze-3-β-sulfatoethylsulfone. The mixture is heated to 55° C., and is maintained at pH 4 to 6 for 4 hours. 
     To the resulting solution is added sodium chloride to precipitate the desired product of formula (35), (λmax=525 nm).                           
     EXAMPLE 36 to 76 
     A procedure similar to that described in Example 35 is repeated; a solution containing the product of Example 34 is reacted with compound listed below (Examples 36 to 76) 
     EXAMPLE 
     No. Compound Used 
     36 1-N-ethylaminobenzene-4-β-sulfatoethylsulfone 
     37 1-N-ethylaminobenzene-2-β-sulfatoethylsulfone 
     38 1-N-ethylamino-4-methoxybenzene-3-β-sulfatoethylsulfone 
     39 1-N-methylaminobenzene-3-β-sulfatoethylsulfone 
     40 1-N-methylaminobenzene-4-β-sulfatoethylsulfone 
     41 1-N-methylaminobenzene-2-β-sulfatoethylsulfone 
     42 1-N-methylamino-4-methoxybenzene-3-β-sulfatoethylsulfone 
     43 1-N-β-carbamoylethylaminobenzene-3-β-sulfatoethylsulfone 
     44 1-N-β-carbamoylethylaminobenzene-4-β-sulfatoethylsulfone 
     45 1-N-β-carbamoylethylaminobenzene-2-β-sulfatoethylsulfone 
     46 1-N-β-carbamoylmethylamino-4-methoxybenzene-3-β-sulfatoethylsulfone 
     47 1-N-n-propylaminobenzene-3-β-sulfatoethylsulfone 
     48 1-N-n-propylaminobenzene-4-β-sulfatoethylsulfone 
     49 1-N-n-propylaminobenzene-2-β-sulfatoethylsulfone 
     50 1-N-n-propylamino-4-methoxybenzene-3-β-sulfatoethylsulfone 
     51 1-N-β-cyanoethylaminobenzene-3-β-sulfatoethylsulfone 
     52 1-N-β-cyanoethylaminobenzene-4-β-sulfatoethylsulfone 
     53 1-N-β-cyanoethylaminobenzene-2-β-sulfatoethylsulfone 
     54 1-N-β-cyanoethylamino-4-methoxybenzene-3-β-sulfatoethylsulfone 
     55 1-N-β-hydroxyethylaminobenzene-3-β-sulfatoethylsulfone 
     56 1-N-β-hydroxyethylaminobenzene-4-β-sulfatoethylsulfone 
     57 1-N-β-hydroxyethylaminobenzene-2-β-sulfatoethylsulfone 
     58 1-N-β-hydroxyethylamino-4-methoxybenzene-3-β-sulfatoethylsulfone 
     59 1-N-β-sulfatoethylaminobenzene-3-β-sulfatoethylsulfone 
     60 1-N-β-methoxycarbonylethylaminobenzene-3-β-sulfatoethylsulfone 
     61 1-N-ethylamino-2-methoxybenzene-5-β-sulfatoethylsulfone 
     62 1-N-ethylamino-2,4-dimethylbenzene-5-β-sulfatoethylsulfone 
     63 1-N-ethylamino-2-methoxy-5-methylbenzene-3-β-sulfatoethylsulfone 
     64 1-N-ethylaminonaphthalene-6-β-sulfatoethylsulfone 
     65 1-N-ethylamino-8-sulfonaphthalene-6-β-sulfatoethylsulfone 
     66 1-N-methylaminonaphthalene-8-β-sulfatoethylsulfone 
     67 1-aminobenzene-4-β-sulfatoethylsulfone 
     68 1-aminobenzene-2-β-sulfatoethylsulfone 
     69 1-N-ethylaminobenzene-3-β-sulfatoethylsulfone 
     70 1-amino-4-methoxybenzene-3-β-sulfatoethylsulfone 
     71 1-amino-2-methoxybenzene-5-β-sulfatoethylsulfone 
     72 1-amino-2-methoxy-5-methylbenzene-4-β-sulfatoethylsulfone 
     73 1-amino-2,4-dimethylbenzene-5-β-sulfatoethylsulfone 
     74 1-aminonaphthalene-6-β-sulfatoethylsulfone 
     75 1-amino-8-sulfonaphthalene-6-β-sulfatoethylsulfone 
     76 1-aminonaphthalene-8-β-sulfatoethylsulfone 
     EXAMPLE 77 
     To a solution containing the compound of Example 1 was added 25.3 parts of 1-aminobenzene-3-β-sulfatoethylsulfone. The mixture was heated to 55° C., and maintained at pH 4 to 5 for 5 hours. To this reaction mixture was added 18.5 parts of 3-carboxypyridine, and the mixture is heated to 85˜90° C., and is maintained at pH 4 to 5 for 12 hours. 
     To the resulting solution is added sodium chloride to precipitate the desired product of formula (77), (λmax=528 nm),                           
     EXAMPLE 78˜118 
     A procedure similar to that described in Example 77 is repeated using the substituents listed in examples 78 to 118 instead of 1-aminobenzene-3-β-sulfatoethylsulfone that used in Examples 77. As a result, bluish red (528±2 nm) monoazo derivatives are obtained. 
     EXAMPLE 
     No. Compound Used 
     78 1-N-ethylaminobenzene-4-β-sulfatoethylsulfone 
     79 1-N-ethylaminobenzene-2-β-sulfatoethylsulfone 
     80 1-N-ethylamino-4-methoxybenzene-3-β-sulfatoethylsulfone 
     81 1-N-methylaminobenzene-3-β-sulfatoethylsulfone 
     82 1-N-methylaminobenzene-4-β-sulfatoethylsulfone 
     83 1-N-methylaminobenzene-2-β-sulfatoethylsulfone 
     84 1-N-methylamino-4-methoxybenzene-3-β-sulfatoethylsulfone 
     85 1-N-β-carbamoylethylaminobenzene-3-β-sulfatoethylsulfone 
     86 1-N-β-carbamoylethylaminobenzene-4-β-sulfatoethylsulfone 
     87 1-N-β-carbamoylethylaminobenzene-2-β-sulfatoethylsulfone 
     88 1-N-β-carbamoylmethylamino-4-methoxybenzene-3-β-sulfatoethylsulfone 
     89 1-N-n-propylaminobenzene-3-β-sulfatoethylsulfone 
     90 1-N-n-propylaminobenzene-4-β-sulfatoethylsulfone 
     91 1-N-n-propylaminobenzene-2-β-sulfatoethylsulfone 
     92 1-N-n-propylamino-4-methoxybenzene-3-β-sulfatoethylsulfone 
     93 1-N-β-cyanoethylaminobenzene-3-β-sulfatoethylsulfone 
     94 1-N-β-cyanoethylaminobenzene-4-β-sulfatoethylsulfone 
     95 1-N-β-cyanoethylaminobenzene-2-β-sulfatoethylsulfone 
     96 1-N-β-cyanoethylamino-4-methoxybenzene-3-β-sulfatoethylsulfone 
     97 1-N-β-hydroxyethylaminobenzene-3-β-sulfatoethylsulfone 
     98 1-N-β-hydroxyethylaminobenzene-4-β-sulfatoethylsulfone 
     99 1-N-β-hydroxyethylaminobenzene-2-β-sulfatoethylsulfone 
     100 1-N-β-hydroxyethylamino-4-methoxybenzene-3-β-sulfatoethylsulfone 
     101 1-N-β-sulfatoethylaminobenzene-3-β-sulfatoethylsulfone 
     102 1-N-β-methoxycarbonylethylaminobenzene-3-β-sulfatoethylsulfone 
     103 1-N-ethylamino-2-methoxybenzene-5-β-sulfatoethylsulfone 
     104 1-N-ethylamino-2,4-dimethylbenzene-5-β-sulfatoethylsulfone 
     105 1-N-ethylamino-2-methoxy-5-methylbenzene-3-β-sulfatoethylsulfone 
     106 1-N-ethylaminonaphthalene-6-β-sulfatoethylsulfone 
     107 1-N-ethylamino-8-sulfonaphthalene-6-β-sulfatoethylsulfone 
     108 1-N-methylaminonaphthalene-8-β-sulfatoethylsulfone 
     109 1-aminobenzene-4-β-sulfatoethylsulfone 
     110 1-aminobenzene-2-β-sulfatoethylsulfone 
     111 1-N-ethylaminobenzene-3-β-sulfatoethylsulfone 
     112 1-amino-4-methoxybenzene-3-β-sulfatoethylsulfone 
     113 1-amino-2-methoxybenzene-5-β-sulfatoethylsulfone 
     114 1-amino-2-methoxy-5-methylbenzene-4-β-sulfatoethylsulfone 
     115 1-amino-2,4-dimethylbenzene-5-β-sulfatoethylsulfone 
     116 1-aminonaphthalene-6-β-sulfatoethylsulfone 
     117 1-amino-8-sulfonaphthalene-6-β-sulfatoethylsulfone 
     118 1-aminonaphthalene-8-3-sulfatoethylsulfone 
     EXAMPLE 119 
     A solution containing 4-nitroaniline-2-sulfonic acid (21.8 parts) and a 35% aqueous solution of sodium nitrite (21.7 parts) in water (150 parts) was introduced into a solution containing ice water (300 parts) and concentrated hydrochloric acid (35.5 parts), while controlling the temperature at 0 to 5° C., and the mixture was stirred for 1 hour at this temperature to effect diazotization. 
     Successively, after excess nitrous acid had been decomposed, 2-N-methylamino-8-hydroxynaphthalene-3,6-disulfonic acid (33.3 parts) was added to the reaction mixture, and the mixture was stirred for 12 hours at room temperature, thereby performing a coupling reaction. Thereafter, the reaction mixture was adjusted to pH 8 to 10, and mixed with sodium sulfide (10.7 parts), and the mixture was heated to 60° C. and stirred for 3 hours at this temperature to effect reduction of the nitro group. Then, the reaction mixture was mixed with sodium chloride (40 parts) to deposit crystals, which were collected and washed. The resulting wet cake was dissolved in water (400 parts). The solution was mixed with cyanuric chloride (16.7 parts), and the mixture was stirred for 5 hours at 0 to 10° C., while controlling the pH within a range of 4 to 5 using a 20% aqueous solution of sodium carbonate, thereby performing a first condensation. To this reaction mixture was added an aqueous solution of 3.78 parts of cyanamide in about 100 parts of water, and the mixture is heated to 40˜60° C. and maintained at a pH 8.0 to 10.0 by means of a 20% aqueous solution of sodium carbonate until the reaction has ended after 6 to 7 hours, thereby performing a second condensation. 
     25.3 parts of 1-aminobenzeze-3-β-sulfatoethylsulfone were added to the above reaction mixture, and the resulting mixture was heated to 55° C., and maintained at pH 4 to 6 for 4 hours. To the resulting solution was added sodium chloride to precipitate the desired product of formula (119), (λmax=530 nm).                           
     EXAMPLE 120 to 193 
     In similar manner compounds (120) to (193) were prepared. Each naphthol compound of formula(XI) shown in a second column of the following table was used in place of 2-N-methylamino-8-hydroxynaphalene-3,6-disulfonic acid, and each compound of the formula (X) shown in a third column in place of 4-nitroaniline-2-sulfonic acid, cyanamide as shown in a fourth column, and each aromatic amine compound of the formula(VIII) shown in a fifth column in place of 1-aminobenzeze-3-β-sulfatoethylsulfone, thereby obtaining the desired corresponding monoazo compound. 
     
       
         
               
               
               
             
               
               
               
               
             
           
               
                   
               
             
             
               
                 Ex. No. 
                 Compound of Formula (V) 
                 Compound of Formula (IX) 
               
               
                   
               
               
                 120 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 121 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 122 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 123 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 124 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 125 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 126 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 127 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 128 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 129 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 130 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 131 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 132 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 133 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 134 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 135 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 136 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 137 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 138 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 139 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 140 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 141 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 142 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 143 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 144 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 145 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 146 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 147 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 148 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 149 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 150 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 151 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 152 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 153 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 154 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 155 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 156 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 157 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 158 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 159 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 160 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 161 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 162 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 163 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 164 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 165 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 166 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 167 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 168 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 169 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 170 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 171 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 172 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 173 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 174 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 175 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 176 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 177 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 178 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 179 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 180 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 181 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 182 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 183 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 184 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 185 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 186 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 187 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 188 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 189 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 190 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 191 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 192 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 193 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
             
          
           
               
                 Ex. No. 
                 Cyanamide 
                 Compound of Formula (III) 
                 Shade 
               
               
                   
               
               
                 120 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 121 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 122 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 123 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 124 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 125 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 126 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 127 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 128 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 129 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 130 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 131 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 132 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 133 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 134 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 135 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 136 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 137 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 138 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 139 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 140 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 141 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 142 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 143 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 144 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 145 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 146 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 147 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 148 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 149 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 150 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 151 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 152 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 153 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 154 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 155 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 156 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 157 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 158 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 159 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 160 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 161 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 162 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 163 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 164 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 165 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 166 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 167 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 168 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 169 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 170 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 171 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 172 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 173 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 174 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 175 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 176 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 177 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 178 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 179 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 180 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 181 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 182 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 183 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 184 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 185 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 186 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 187 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 188 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 189 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 190 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 191 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 192 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 193 
                 NH 2 CN 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
             
          
         
       
     
     EXAMPLE 194 
     To an aqueous mixture of the dichloro triazine described in example 119 was added 1-aminobenzeze-3-β-sulfatoethylsulfone (25.3 parts), and the mixture is heated to 55° C. and maintained at a pH 4 to 5 by means of a 20% aqueous solution of sodium carbonate until the reaction was complete after 3 to 5 hours. 
     18.5 parts of 3-carboxypyridine were added to the above reaction mixture, and the resulting mixture was heated to 85˜90° C. at pH 4 to 5 for 12 hours. To the resulting solution was added sodium chloride to precipitate the desired product of formula (194), (λmax=535 nm).                           
     EXAMPLE 195 to 268 
     In a similar manner compounds (195) to (268) were prepared. Each naphthol compound of formula (XI) shown in a second column of the following table was used in place of 2-N-methylamino-8-hydroxynaphthalene-3,6-disulfonic acid, and each compound of the formula (X) shown in a third column in place of 4-nitroaniline-2-sulfonic acid, 3-carboxypyridine as shown in a fourth column, and each aromatic amine compound of the formula(VIII) shown in a fifth column in place of 1-aminobenzeze-3-β-sulfatoethylsulfone, thereby obtaining the desired corresponding monoazo compound. 
     
       
         
               
               
               
             
               
               
               
               
             
           
               
                   
               
             
             
               
                 Ex. No. 
                 Compound of Formula (XI) 
                 Compound of Formula (X) 
               
               
                   
               
               
                 195 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 196 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 197 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 198 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 199 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 200 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 201 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 202 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 203 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 204 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 205 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 206 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 207 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 208 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 209 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 210 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 211 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 212 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 213 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 214 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 215 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 216 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 217 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 218 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 219 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 220 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 221 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 222 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 223 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 224 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 225 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 226 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 227 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 228 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 229 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 230 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 231 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 232 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 233 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 234 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 235 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 236 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 237 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 238 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 239 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 240 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 241 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 242 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 243 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 244 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 245 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 246 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 247 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 248 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 249 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 250 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 251 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 252 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 253 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 254 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 255 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 256 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 257 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 258 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 259 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 260 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 261 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 262 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 263 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 264 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 265 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 266 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 267 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 268 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
             
          
           
               
                 Ex. No. 
                 3-Carboxypyridine 
                 Compound of Formula (VIII) 
                 Shade 
               
               
                   
               
               
                 195 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 196 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 197 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 198 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 199 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 200 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 201 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 202 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 203 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 204 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 205 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 206 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 207 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 208 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 209 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 210 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 211 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 212 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 213 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 214 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 215 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 216 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 217 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 218 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 219 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 220 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 221 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 222 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 223 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 224 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 225 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 226 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 227 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 228 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 229 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 230 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 231 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 232 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 233 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 234 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 235 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 236 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 237 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 238 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 239 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 240 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 241 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 242 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 243 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 244 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 245 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 246 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 247 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 248 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 249 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 250 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 251 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 252 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 253 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 254 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 255 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 256 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 257 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 258 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 259 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 260 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 261 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 262 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 263 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 264 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 265 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 266 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 267 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 268 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
             
          
         
       
     
     EXAMPLE 269 
     2-Amino-8-hydroxynaphthalene-6-disulfonic acid (23.8 parts) was added to 4-nitro-2-sulphobenzene diazonium chloride prepared as in Example 1, and the mixture was stirred for 12 hours at room temperature, to effect coupling. The reaction mixture was then adjusted to pH 8 to 10, and mixed with sodium sulfide (10.7 parts), and the mixture was heated to 60.° C. and stirred for 3 hours at this temperature to reduce the nitro group. Then, the reaction mixture was mixed with sodium chloride (40 parts) to deposit a solid, which was collected and washed. The resulting wet cake was dissolved in water (400 parts). The solution was mixed with cyanuric chloride (16.7 parts), and the mixture was stirred for 5 hours at 0 to 10° C., while controlling the pH within a range of 4 to 5 using a 20% aqueous solution of sodium carbonate, thereby performing a first condensation. To this reaction mixture was added 1-N-ethylaminobenzene-3-β-sulfatoethylsulfone (27.8 parts), and the mixture is heated to 55° C. and maintained at a pH 4 to 5 by means of a 20% aqueous solution of sodium carbonate until the reaction has ended after 3 to 5 hours. 
     To the resulting solution is added sodium chloride to precipitate the desired product of formula (269), (λmax=518 nm),                           
     EXAMPLE 270 to 295 
     By a similar procedure compounds of examples 270 to 295 were prepared. Each naphthol compound of formula (XI) shown in a second column of the following table was used in place of 2-amino-8-hydroxynaphthalene-6-disulfonic acid, and each compound of the formula (X) shown in a third column in place of 4-nitroaniline-2-sulfonic acid, cyanuric chloride or cyanuric fluoride as shown in a fourth column in which Cl and F denote cyanuric chloride and cyanuric fluoride, and each aromatic amine compound of the formula (VIII) shown in a fifth column in place of 1-N-ethylaminobenzene-3-β-sulfatoethylsulfone, thereby obtaining the desired corresponding monoazo compound. 
     
       
         
               
               
               
               
               
               
             
           
               
                   
               
               
                   
                   
                   
                 Cyanuric 
                   
                   
               
               
                   
                   
                   
                 chloride or 
               
               
                 Ex. 
                 Compound of 
                 Compound of 
                 Cyanuric 
                 Compound of 
               
               
                 No. 
                 Formula (XI) 
                 Formula (X) 
                 fluoride 
                 Formula (VIII) 
                 Shade 
               
               
                   
               
             
             
               
                 270 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Cl 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 271 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Cl 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 272 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Cl 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 273 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Cl 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 274 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Cl 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 275 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Cl 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 276 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Cl 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 277 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Cl 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 278 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 F 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 279 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 F 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 280 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 F 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 281 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 F 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 282 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 F 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 283 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 F 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 284 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 F 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 285 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 F 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 286 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 F 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 287 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 F 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 288 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 F 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 289 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 F 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 290 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 F 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 291 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 F 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 292 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 F 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 293 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 F 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 294 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 F 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
               
                 295 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 F 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Bluish red 
               
               
                   
               
             
          
         
       
     
     EXAMPLE 296 
     Urea 100 parts, m-nitrobenzene sulfonic acid sodium salt, 10 parts, sodium bicarbonate, 20 parts, sodium alginate, 55 parts, warm water, 815 parts, were stirred in a vessel to give a completely homogeneous printing paste. 
     Dyestuff of formula (2) (prepared as in example 2), 3 parts, and the above printing paste, 100 parts, were mixed together to make a homogeneous colored paste. A 100 mesh printing screen covering an adequate sized piece of cotton fabric was painted with this colored paste on printing screen to give a colored fabric. 
     The colored fabric was placed in an oven at 65° C. to dry for 5 minutes then taken out, and put into a steam oven using saturated steam for 10 minutes at 102-105° C. 
     The colored fabric was washed with cold water, hot water, and soap then dried to obtain a bluish red fabric with good build-up, light fastness, wet fastness and wash fastness. 
     EXAMPLE 297 
     Dyestuff of formula (2) (prepared from the example 2), 3 parts was dissolved in 100 parts of water to give a padding liquor. 25 ml of alkali solution (NaOH (38° Be′) 15 ml/l Glauber&#39;s salt 30 parts/l) were added to the padding liquor. The resultant solution was put into a pad roller machine. The cotton fabric was padded by the roller pad machine, then was batched for 4 hours. The padded fabric was washed with cold water, hot water, and soap solution then dried to obtain a bluish red fabric with good build-up, light fastness, wet fastness and wash fastness. 
     EXAMPLE 298 
     Dyestuff of formula (2) (prepared from the example 2), 0.25 parts was dissolved in 250 parts of water. To 40 ml of this solution, in a dyeing bottle, was added cotton fabric, Glauber&#39;s salt,2.4 parts, and 32% alkali solution, 2.5 parts. The dyeing bottle was shaken at 60° C. for 60 minutes. The colored fabric was washed with cold water, hot water, and soap solution then dried to obtain a bluish red fabric with good build-up, light fastness, wet fastness and wash fastness. 
     EXAMPLE 299 
     Dyestuff of the formula (35), (prepared as described in Example 35) 0.25 parts was dissolved in 250 parts of water. To 40 ml of this solution, in a dyeing bottle, was added cotton fabric, Glauber&#39;s salt,2.4 parts, and 32% alkali solution, 2.5 parts. The dyeing bottle was shaken at 60° C. for 60 minutes. The colored fabric was washed with cold water, hot water, and soap solution then dried to obtain a bluish red fabric with good build-up, light fastness, wet fastness and wash fastness. 
     EXAMPLE 300 
     Dyestuff of the formula (77), (prepared as described in Example 77) 0.25 parts was dissolved in 250 parts of water. To 40 ml of this solution, in a dyeing bottle, was added cotton fabric, Glauber&#39;s salt,2.4 parts, and 32% alkali solution, 2.5 parts. The dyeing bottle was shaken at 60° C. for 60 minutes. The colored fabric was washed with cold water, hot water, and soap solution then dried to obtain a bluish red fabric with good build-up, light fastness, wet fastness and wash fastness. 
     EXAMPLE 301 
     Dyestuff of the formula (119), (prepared as described in Example 119)0.25 parts was dissolved in 250 parts of water. To 40 ml of this solution, in a dyeing bottle, was added cotton fabric, Glauber&#39;s salt, 2.4 parts, and 32 % alkali solution, 2.5 parts. The dyeing bottle was shaken at 60° C. for 60 minutes. The colored fabric was washed with cold water, hot water, and soap solution then dried to obtain a bluish red fabric with good build-up, light fastness, wet fastness and wash fastness. 
     EXAMPLE 302 
     Dyestuff of the formula (194), (prepared as described in Example 194) 0.25 parts was dissolved in 250 parts of water. To 40 ml of this solution, in a dyeing bottle, was added cotton fabric, Glauber&#39;s salt, 2.4 parts, and 32 % alkali solution, 2.5 parts. The dyeing bottle was shaken at 60° C. for 60 minutes. The colored fabric was washed with cold water, hot water, and soap solution then dried to obtain a bluish red fabric with good build-up, light fastness, wet fastness and wash fastness. 
     EXAMPLE 303 
     Dyestuff of the formula (269), (prepared as described in Example 269) 0.25 parts was dissolved in 250 parts of water. To 40 ml of this solution, in a dyeing bottle, was added cotton fabric, Glauber&#39;s salt, 2.4 parts, and 32 % alkali solution, 2.5 parts. The dyeing bottle was shaken at 60° C. for 60 minutes. The colored fabric was washed with cold water, hot water, and soap solution then dried to obtain a bluish red fabric with good build-up, light fastness, wet fastness and wash fastness. 
     Although the present invention has been explained in relation to its preferred embodiment, it is to be understood that many other possible modifications and variations can be made without departing from the spirit and scope of the invention as hereinafter claimed.