Patent Abstract:
Diaminopyridine-based azo dyes for cellulose-containing fibers, represented by the following formula: ##STR1## and the other is hydrogen, phenyl, benzyl, allyl, or alkyl which are unsubstituted or substituted by hydroxyl or lower alkoxy 
     (wherein 
     A is methylene, ethylene, propylene, or 1,3-butylene; 
     n is 0 or 1; 
     Y 1  and Y 2 , which are the same or different, are hydrogen, alkyl, alkenyl, cyclohexyl, aryl, or aralkyl which are unsubstituted or substituted by cyano, hydroxy, lower alkoxy, or dialkylamino, or Y 1  and Y 2  together form a 5- or 6-membered heterocyclic ring (NY 1  Y 2 ) containing one nitrogen, the total number of carbon atoms of Y 1  and Y 2  being 18 or less; 
     R 1  is nitro, cyano, methylsulfonyl, phenylsulfonyl, mono-lower alkylaminosulfonyl, di-lower alkylaminosulfonyl, acetyl, or benzoyl; 
     R 2  and R 3 , which are the same or different, are hydrogen, trifluoromethyl, halogen, or cyano; 
     R 4  is hydrogen, lower alkyl, mono- or di-lower alkylaminosulfonyl, mono/or di-lower alkylcarbamoyl, or acetylamino; 
     R 5  and R 6 , which are the same or different, are hydrogen, halogen, or lower alkyl; 
     R 7  is lower alkyl; 
     R 8  is trifluoromethyl, or halogen; and 
     R 9  is hydrogen, or halogen). 
     The dyes are useful for dyeing cellulose-containing fibers, particularly cellulose fibers and mixed fibers of polyester fibers and cellulose fibers in from orange to blue.

Full Description:
FIELD OF THE INVENTION 
     The present invention relates to diaminopyridine-based azo dyes for cellulose-containing fibers. More particularly, it relates to reactive azo dyes for use in dyeing of cellulose-containing fibers, particularly cellulose fibers and mixed fibers of polyester fibers and cellulose fibers in from orange to blue having excellent fastness to light, etc. 
     SUMMARY OF THE INVENTION 
     The present invention is to provide diaminopyridine-based azo dyes for cellulose-containing fibers, represented by the general formula (I): ##STR2## and the other is a hydrogen atom, a phenyl group, a benzyl group, an allyl group, or an alkyl group which may be substituted by a hydroxyl group or a lower alkoxy group 
     (wherein) 
     A is a methylene group, an ethylene group, a propylene group, or a 1,3-butylene group; 
     n is 0 or 1; 
     Y 1  and Y 2  are each a hydrogen atom, or an alkyl group, an alkenyl group, a cyclohexyl group, an aryl group, or an aralkyl group which may all be substituted by a cyano group, a hydroxy group, a lower alkoxy group, or a dialkylamino group, and they may combine together in combination with nitrogen to form a 5- or 6-membered nitrogen-containing heterocylic ring (NY 1  Y 2 ), the total number of carbon atoms of Y 1  and Y 2  being 18 or less; 
     R 1  is a nitro group, a cyano group, a methylsulfonyl group, a phenylsulfonyl group, a mono-lower alkylaminosulfonyl group, a di-lower alkylaminosulfonyl group, an acetyl group, or a benzoyl group; 
     R 2  and R 3  are each a hydrogen atom, a trifluoromethyl group, a halogen atom, or a cyano group; 
     R 4  is a hydrogen atom, a lower alkyl group, a mono- or di-lower alkylaminosulfonyl group, a mono- or di-lower alkylcarbamoyl group, or an acetylamino group; 
     R 5  and R 6  are each a hydrogen atom, a halogen atom, or a lower alkyl group; 
     R 7  is a lower alkyl group; 
     R 8  is a trifluoromethyl group, or a halogen atom; and 
     R 9  is a hydrogen atom, or a halogen atom). 
     DETAILED DESCRIPTION OF THE INVENTION 
     The dyes represented by the general formula (I) can be easily prepared, for example, by reacting compounds represented by the general formula (IV): ##STR3## and the other is a hydrogen atom, a phenyl group, a benzyl group, an allyl group, or an alkyl group which may be substituted by a hydroxyl group or a lower alkoxy group, and A and n are the same as described hereinbefore) with compounds represented by the general formula (V): ##STR4## (wherein Y 1  and Y 2  are the same as described hereinbefore) in a solvent, e.g., N-methyl-2-pyrrolidone. 
     Halogen atoms as indicated by R 2 , R 3 , R 5 , R 6 , R 8  and R 9  in the general formulae (I) and (IV) include a fluorine atom, a chlorine atom, and a bromine atom. Lower alkyl groups as indicated by R 4  and R 5  include a methyl group, an ethyl group, and a straight or branched alkyl group containing from 3 to 4 carbon atoms. 
     Alkyl groups as indicated by X 1 , X 2 , Z 1  and Z 2  include a methyl group, an ethyl group, and a straight alkyl group containing from 3 to 6 carbon atoms. Examples of alkyl groups substituted by a hydroxyl group include a 2-hydroxyethyl group, a 3-hydroxypropyl group, a 2-hydroxypropyl group, a 2-hydroxybutyl group, a 4-hydroxybutyl group, a 1,1-dimethyl-2-hydroxyethyl group, a 5-hydroxypentyl group, a 6-hydroxyhexyl group, a (β-hydroxy)ethoxyethyl group, a (γ-hydroxy)propoxypropyl group, and a (β-hydroxy)ethoxyethoxyethyl group. Examples of alkyl groups substituted by a lower alkoxy group include a 2-methoxyethyl group, a 2-ethoxyethyl group, a 3-methoxypropyl group, a 3-isopropoxypropyl group, a methoxyethoxyethyl group, an ethoxyethoxypropyl group, a methoxyisopropoxyethyl group, and a methoxyethoxyethoxyethyl group. 
     Alkyl groups as indicated by Y 1  and Y 2  in the general formulae (I) and (V) include a methyl group, an ethyl group, and a straight or branched alkyl group containing from 3 to 18 carbon atoms. Examples of substituted alkyl groups include cyano group-, hydroxyl group-, lower alkoxy group-, or dialkylamino group-substituted alkyl groups, such as a cyanomethyl group, a 2-cyanoethyl group, a 3-cyanopropyl group, a 2-hydroxyethyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 4-hydroxybutyl group, a 2-(2-hydroxyethoxy)ethyl group, a tris(hydroxymethyl)methyl group, a 2-ethoxyethyl group, a 3-isopropoxypropyl group, a 3-(2-methoxyethoxy)propyl group, a 2,2-diethoxyethyl group, a 2-(N,N-diethylamino)ethyl group, a 2-(N,N-dimethylamino)ethyl group, and a 3-(N,N-dimethylamino)propyl group. 
     Alkenyl groups include an allyl group, a 2-methylallyl group, a 3-methylallyl group, and a straight or branched alkenyl group containing from 4 to 18 carbon atoms. Substituted alkenyl groups include cyano group-, hydroxy group-, or lower alkoxy group-substituted alkenyl groups, such as a 3-cyanoallyl group, a 2-hydroxyallyl group, a 3-methoxyethoxyallyl group, and a 1-methyl-3-(N,N-diethylamino)allyl group. 
     Aryl groups include a phenyl group, a naphthyl group, an o-tolyl group, and a p-butylphenyl group. Examples of aryl groups substituted by a cyano group, a hydroxy group, a lower alkoxy group, or a dialkylamino group include an m-cyanophenyl group, a p-hydroxyphenyl group, a p-methoxyphenyl group, a p-(2-methoxyethoxy)phenyl group, a 2,5-dimethoxyphenyl group, and a p-(N,N-dimethylamino)phenyl group. 
     Aralkyl groups include a benzyl group, a phenetyl group, an m-methylbenzyl group, and a p-methylphenetyl group. Examples of substituted aralkyl groups include an m-cyanobenzyl group, a p-hydroxybenzyl group, a p-hydroxyphenetyl group, and an o-anisyl group. 
     Nitrogen-containing heterocyclic groups as represented by NY 1  Y 2  include a 1-pyrrolidinyl group, a 3-methyl-1-pyrrolidinyl group, a 2-hydroxyethyl-1-pyrrolidinyl group, a 2,5-dimethyl-1-pyrrolidinyl group, a 3-thiazolidinyl group, a 1-pyrrolyl group, a 1-pyrazolyl group, a 1-imidazolyl group, a morpholino group, a piperidino group, a 2,6-dimethylpiperidino group, a 1-piperadinyl group, and a 4-methyl-1-piperazinyl group. 
     Of the compounds represented by NY 1  Y 2 , di-substituted amino groups having a total number of carbon atoms of from 6 to 12 are particularly preferred. 
     When n is 0, in particular, light fastness is excellent. 
     In preparing the disazo dyes of the general formula (I), disazo compounds represented by the general formula (II) are added to from 1 to 1.2 moles of difluorotriazines represented by the general formula (III), per mole of the disazo compound, and they are heated at a temperature of from 40° to 90° C. for a period of from 0.5 to 5 hours in an organic solvent, such as acetone, methyl ethyl ketone, toluene, nitrobenzene, dioxane, N,N-dimethylformaldehyde, N-methyl-2-pyrrolidone, or dimethylsulfoxide, in the presence of from 1 to 2 moles per mole of the disazo compound of an acid coupler, such as tertiary amine, e.g., triethylamine, tributylamine, or N,N-diethylaniline, and inorganic base, e.g., potassium carbonate, or potassium hydrogencarbonate. The reaction solution is then cooled and poured into, for example, water to form a precipitate. By separating the precipitate by techniques such as filtration and centrifugal separation, there can be almost quantitatively obtained the disazo dyes represented by the general formula (I). 
     Cellulose-containing fibers which are to be dyed with the dyes represented by the general formula (I) include fibers such as natural fibers, e.g., cotton and flax, semi-synthetic fibers, e.g., viscose rayon and copper ammonia rayon, and modified cellulose fibers, e.g., partially aminated or partially acylated cellulose fibers, and their fabrics, unwoven fabrics, and so forth. In addition, mixed fibers of cellulose fibers and other fibers, such as polyester fibers, cation dyeable polyester fibers, anion dyeable polyester fibers, polyamide fibers, wool, acryl fibers, urethane fibers, diacetate fibers, and triacetate fibers, and their fabrics can be used. Of the above-described fibers and fabrics, cellulose fibers, mixed fibers of cellulose fibers and polyester fibers, and their fabrics are particularly suitable for dyeing with the dyes of the general formula (I). 
     In the practice of dyeing, it is desirable that the dye of the general formula (I) is finely dispersed in a medium so that the grain size is from about 0.5 to 2 microns. 
     Various techniques can be employed for such fine dispersion, including a method in which a nonionic or Pluronic surface active agent, an anionic dispersant, such as sodium ligninsulfonate, or a water-soluble dispersant, such as a sodium salt of a naphthalene-sulfonic acid-formalin condensate, is employed, and the dye is finely dispersed in water by the use of a grinder such as a sand grinder and a mill; a method in which a water sparingly soluble or water-insoluble dispersant, such as a compound prepared by adding a low molecular amount of ethylene oxide to sulfosuccinic acid ester, nonylphenol, or the like, is employed, and the dye is finely dispersed in a solvent other than water, such as alcohols, e.g., ethyl alcohol, isopropyl alcohol, and polyethylene glycol, ketones, e.g., acetone and methyl ethyl ketone, hydrocarbons, e.g., n-hexane, toluene, xylene, and mineral turpentine, halogenated hydrocarbons, e.g., tetrachloroethylene, esters, e.g., ethyl acetate and butyl acetate, ethers, e.g., dioxane, and tetraethylene glycol dimethyl ether, and their mixed solvents, and a method in which the dye is finely dispersed in a mixture of water and a solvent compatible with water in any proportion, selected from the above-described solvents. 
     In addition, a polymeric compound soluble in each dispersant, a surface active agent having mainly a function other than the dispersion action, etc., may be added in the course of the fine dispersion. 
     The finely dispersed dye solution can be used as such as a padding bath for use in a padding dyeing method, or as a printing color paste for use in a printing method. It is usual, however, that the finely dispersed dye solution is diluted with water, a mixture of water and a solvent compatible with water in any proportion, an o/w emulsion in which the oil phase is petroleum hydrocarbon such as mineral turpentine or halogenated hydrocarbon such as tetrachloroethylene, or a w/o emulsion in which the oil phase is the same as above to a level determined depending on the desired dyeing concentration and, thereafter, is used as a padding bath or a printing color paste. 
     In the preparation of such padding baths and printing color pastes, a cellulose fiber-swelling agent can be added for advantageously effecting dyeing, or alkali metal compounds, organic epoxy compounds, organic vinyl compounds, etc., can be added as acid couplers for the purpose of accelerating the reaction between the dye and cellulose fibers. Alkali metal compounds which can be used include alkali metal carbonic acid salts, alkali metal hydrocarbonic acid salts, alkali metal phosphoric acid salts, alkali metal boric acid salts, alkali metal silicic acid salts, alkali metal hydroxides, alkali metal aliphatic acid salts, e.g., alkali metal acetic acid salts, and alkali metal precursors which generate alkalis when heated in the presence of water, such as sodium trichloroacetate and sodium acetoacetate. The amount of the alkali metal compound being used is usually sufficient to be such that the pH of the padding bath or printing color paste is from 7.5 to 8.5. Organic epoxy compounds which can be used include ethylene glycol diglycidyl ether and polyethylene glycol diglycidyl ether having an average molecular weight of from 150 to 400.  Organic vinyl compounds include ethylene glycol diacrylate and diacrylate or dimethacrylate of polyethylene glycol having an average molecular weight of from 150 to 400. The amount of the organic epoxy compound or organic vinyl compound being used is from about 3 to 6% by weight based on the padding bath or printing color paste. 
     In order to prevent dry migration during padding dyeing, or to regulate the color paste viscosity to the optimum level in various printing methods, a tackifier such as a water-soluble polymer, e.g., sodium alginate, may be added. 
     The preparation of padding bath or printing color paste is not limited to the above-described methods. It is not always necessary for the cellulose swelling agent and acid coupler to be present in the padding bath or printing color paste, and they may be added in advance to cellulose fibers. Any cellulose fiber-swelling agents can be used as long as they have a boiling point of at least 150° C. and have the effect of swelling cellulose fibers. Examples are ureas, such as N,N,N&#39;,N&#39;-tetramethylurea, polyhydric alcohols, such as polyethylene glycol and polypropylene glycol, and their derivatives. In particular, polyhydric alcohol derivatives which are prepared by dimethylating or diacetylating both terminal hydroxy groups of polyethylene glycol, polypropylene glycol, or the like having an average molecular weight of from about 200 to 500 and which do not react with the reactive groups of the dye are preferred as cellulose fiber swelling agents. 
     The amount of the cellulose fiber-swelling agent used is appropriately from 5 to 25% by weight, preferably from 8 to 15% by weight, based on the padding bath or printing color paste. 
     The above-described cellulose-containing fibers are dyed with the dyes represented by the general formula (I) by the usual method. For example, a cellulose-containing fiber material is impregnated or printed with a padding bath or printing color pastes as prepared by the above-described method, heat-treated with hot air or super heated steam maintained at 160° to 220° C. for 0.5 to 10 minutes, or treated in high pressure saturated steam maintained at 120° to 150° C. for 3 to 30 minutes and, thereafter, washed with heated water containing a surface active agent, an o/w or w/o emulsion cleaning bath in which the oil phase is halogenated hydrocarbon such as tetrachloroethylene, or by the usual dry cleaning method. 
     In accordance with the above-described method, there can be obtained a dyed product which is sharp and uniformly dyed in a color having good light fastness and moisture fastness. 
    
    
     The following examples are given to illustrate the invention in greater detail although the invention is not limited thereto. All parts are by weight. 
     EXAMPLE 1 
     A dye composition consisting of 15 parts of a disazo dye represented by the formula: ##STR5## 15 parts of a naphthalenesulfonic acid-formaldehyde condensate, and 70 parts of water was finely dispersed by the use of a paint shaker as a finely dispersing apparatus to prepare a dye dispersion. The thus-prepared dye dispersion was used to prepare a printing color paste having the following composition: 
     
         ______________________________________                 parts______________________________________Dye dispersion         6.55% Aqueous sodium alginate solution                  55Polyethylene glycol dimethyl ethyl                  9having an average molecular weightof 400Water                  29.5Total                  100    (pH: 8.0)______________________________________ 
    
     A polyester/cotton mixed cloth (mixing ratio: 65/35) was printed with the above-prepared printing color paste by the use of a screen printing machine, which was then subjected to intermediate drying at 80° C. for 3 minutes and fixed by dry heating at 215° C. for 90 seconds. The cloth was washed with water and, thereafter, was subjected to soaping using a cleaning liquid containing 2 g/l of a nonionic surface active agent (Scorerol #900 (trade name) produced by Kao Sekken Co., Ltd.) at 80° C. for 20 minutes at a bath ratio of 1:30. There was thus obtained a product dyed in red having excellent light fastness and wet color fastness. 
     The dye used in this example was prepared as follows. 3&#39;,4&#39;-Dichloro-4-aminoazobenzene was diazotized by the usual method and coupled with 2-(m-hydroxy)anilinio-3-cyano-4-methyl-6-(γ-methoxypropylamino)pyridine to obtain a dye. A mixture of 5.76 g of the above-obtained dye, 2.1 g of 2,4-difluoror-6-(diethyl)aminotriazine, 1.0 g of triethylamine, and 1.0 g of anhydrous potassium carbonate was added to 100 ml of acetone and heated at reflux for 3 hours to achieve a condensation reaction. The reaction solution was then added dropwise to 1,000 ml of water to form a precipitate. The precipitate was separated by filtration, washed with water, and dried at room temperature to obtain 7.1 g of red powder of the dye represented by the above-described formula (yield: 95%). For this dye, λmax (acetone) was 505 nm. 
     EXAMPLE 2 
     A dye composition consisting of 15 parts of a disazo dye represented by the formula: ##STR6## 10 parts of a Pluronic surface active agent (Pluronic L64 (trade name) produced by Asahi Denka Kogyo Co., Ltd.), and 75 parts of water was finely dispersed by the use of a sand grinder as a finely dispersing apparatus to prepare a dye dispersion. This dye dispersion was used to prepare a printing color paste having the following composition: 
     
         ______________________________________                 parts______________________________________Dye dispersion         75% Aqueous sodium alginate solution                  55Diacetate of polypropylene glycol                  10having an average molecular weightof 300Polyethylene glycol diglycidyl ether                  3having an average molecular weightof 200Water                  25Total                  100    (pH: 6.5)______________________________________ 
    
     A cotton broad (cotton yarn number: 40) which had been subjected to silket processing was printed with the above-prepared printing color paste by the use of a screen printing machine, was subjected to intermediate drying at 80° C. for 3 minutes, and then, was treated with super heated steam at 185° C. for 7 minutes. Thereafter, washing processing was performed in the same manner as in Example 1, and there was thus obtained a product dyed in red having excellent light fastness and wet color fastness. 
     The dye used in this example was prepared as follows. 2&#39;-Trifluoromethyl-4&#39;-chloro-4-aminoazobenzene was diazotized by the usual method and coupled with 2-(p-hydroxy)anilino-3-cyano-4-methyl-6-(β-hydroxyethylamino)pyridine to prepare a dye. The dye thus obtained was reacted with 2,4-difluoro-6-[di(n-propyl)amino]triazine in N-methyl-2-pyrrolidone by the use of triethylamine as an acid-removing agent to obtain the dye represented by the above-described formula. For this dye, λmax (acetone) was 506 nm. 
     EXAMPLE 3 
     A dye composition consisting of 10 parts of a disazo dye represented by the formula: ##STR7## 2 parts of polyoxyethylene glycol nonylphenyl ether (HLB: 8.9), and 88 parts of diethylene glycol diacetate was ground by the use of a paint conditioner as a finely dispersing apparatus to prepare a dye ink. 
     A mixture of 10 parts of the dye ink as prepared above and 55 parts of mineral turpentine was gradually poured into 35 parts of an aqueous solution having the composition as described hereinafter while stirring by a homomixer at 5,000 to 7,000 rpm, and the resulting mixture was then stirred until it became uniform to prepare a viscous o/w emulsion type color paste. 
     
         ______________________________________Composition of Aqueous Solution                parts______________________________________Water                  31Repitol G (trade name, special                  3.8nonionic surface active agent,produced by Dai-ichi Kogyo SeiyakuCo., Ltd.)Sodium trichloroacetate                  0.1Total                  34.9______________________________________ 
    
     Using the above-prepared color paste, a polyester/cotton mixed cloth (mixing ratio: 65/35) was printed by the use of a screen printing machine, which was then dried at 100° C. for 2 minutes and treated with super heated steam at 175° C. for 7 minutes. Thereafter, when the cloth was washed with a hot tetrachloroethylene bath containing a small amount of water and dried, there was obtained a product dyed in red having excellent light fastness and wet color fastness and free from contamination in the white background. 
     The dye used in this example was prepared as follows. 3&#39;,5&#39;-Dichloro-3-methyl-4-aminoazobenzene was diazotized by the usual method and coupled with 2-ethoxyethylamino-3-cyano-4-methyl-6-(p-hydroxyphenylethylamino)pyridine to prepare a dye. The dye thus prepared was then reacted with 2,4-difluoro-6-piperidinotriazine in the same manner as in Example 1 to obtain the desired dye. For this dye, λmax (acetone) was 506 nm. 
     EXAMPLE 4 
     A dye composition consisting of 16 parts of a disazo dye represented by the formula: ##STR8## 7 parts of polyoxyethylene glycol nonylphenyl ether (HLB: 13.3), 3 parts of a naphthalenesulfonic acid-formaldehyde condensate, and 74 parts of water was finely dispersed by the use of a sand grinder to prepare a dye dispersion. This dye dispersion was used to prepare a padding bath having the following composition: 
     
         ______________________________________                 parts______________________________________Dye dispersion         6Tetraethylene glycol dimethyl ether                  15Water                  79Total                  100    (pH: 8.0)______________________________________ 
    
     A polyester/cotton mixed cloth (mixing ratio: 65/35) was impregnated with the above-prepared padding bath, squeezed at a squeezing ratio of 45%, dried at 100° C. for 2 minutes, and fixed by dry heating at 200° C. for 1 minute. By washing the cloth with a hot ethanol bath, there was obtained a product dyed in red having excellent light fastness and wet color fastness. 
     The dye used in this example was prepared in the same manner as in Example 1. For this dye, λmax (acetone) was 506 nm. 
     EXAMPLE 5 
     Printing was performed in the same manner as in Example 1 except that a nylon/rayon mixed cloth (mixing ratio: 50/50) was used, and the dry heating fixing temperature was 185° C. There was obtained a product dyed in red having good wet color fastness and light fastness. 
     EXAMPLE 6 
     Using a series of disazo dyes as shown in Tables 1 to 15, printing was performed in the same manner as in Example 1. All dyed products had good light fastness and wet color fastness. The hue of each dyed cloth and λmax (acetone) of dye are shown in Tables 1 to 15. 
     
                                           TABLE 1__________________________________________________________________________ ##STR9## No.    ##STR10##      ##STR11##              X           Z            Hue of Dyed                                            λmax (acetone)                                            (nm)__________________________________________________________________________    ##STR12##      ##STR13##             H           N(C.sub.3 H.sub.6 CN).sub.2                                      red   505  2    ##STR14##     &#34;       CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                          ##STR15##    &#34;    504  3    ##STR16##     &#34;       &#34;           N[C.sub.3 H.sub.7 (n)].sub.2                                       &#34;    505  4    ##STR17##      &#34;      &#34;                          ##STR18##   &#34;     &#34;  5   &#34;      ##STR19##             C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.2 H.sub.5                         N(CH.sub.2CHCH.sub.2).sub.2                                       &#34;    506  6   &#34;      ##STR20##             &#34;           NH.sub.2     deep red                                            510  7    ##STR21##      ##STR22##             &#34;                          ##STR23##   red   506  8    ##STR24##      ##STR25##              ##STR26##                          ##STR27##    &#34;    505  9   &#34;      ##STR28##             &#34;           N(CH.sub.2 CH.sub.2 CH.sub.2 OH).sub.2                                       &#34;    508  10    ##STR29##      ##STR30##             &#34;                          ##STR31##    &#34;    504  11   &#34;      &#34;              ##STR32##  N[C.sub.5 H.sub.11 (n)].sub.2                                       &#34;    &#34;12 &#34;      ##STR33##             &#34;                          ##STR34##    &#34;    506  13    ##STR35##      ##STR36##             CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                          ##STR37##   deep red                                            510  14   &#34;      &#34;       &#34;                          ##STR38##    &#34;    &#34;  15   &#34;      ##STR39##             C.sub.3 H.sub.7 (i)                         N[C.sub.3 H.sub.6 N(CH.sub.3).sub.2                                       &#34;sub.2                                            512  16    ##STR40##      ##STR41##             &#34;           N[C.sub.9 H.sub.19 (n)].sub.2                                       &#34;    510  17   &#34;      &#34;       &#34;           NHC.sub.7 H.sub.15 (n)                                       &#34;    &#34;  18   &#34;      ##STR42##             CH.sub.2 CH.sub.2 CH.sub.2 OH                          ##STR43##    &#34;    513__________________________________________________________________________ 
    
     
                                           TABLE 2__________________________________________________________________________ ##STR44## No.    ##STR45##       ##STR46##              X            Z           Dyed ClothHue                                             (nm)(acetone)λmax__________________________________________________________________________19    ##STR47##       ##STR48##             C.sub.4 H.sub.9 (i)                           ##STR49##  red   506  20    ##STR50##      &#34;      CH.sub.3                           ##STR51##  &#34;     &#34;  21   &#34;       ##STR52##             C.sub.2 H.sub.4 OCH.sub.3                           ##STR53##  deep red                                            510  22    ##STR54##       ##STR55##             &#34;                           ##STR56##  red   506  23    ##STR57##      &#34;      &#34;                           ##STR58##  &#34;     &#34;  24    ##STR59##       ##STR60##              ##STR61##   NH.sub.2    &#34;     508  25   &#34;       ##STR62##             CH.sub.2CHCH.sub.2                          N[C.sub.3 H.sub.7 (i)].sub.2                                      &#34;     506  26    ##STR63##      &#34;      C.sub.2 H.sub.4 OCH.sub.3                          NHC.sub.3 H.sub.7 (i)                                      deep red                                            509  27    ##STR64##      &#34;      &#34;            N(C.sub.2 H.sub.4 CN).sub.2                                      red   506  28    ##STR65##      &#34;      H            N(CH.sub.2CHCH.sub.2).sub.2                                      &#34;     &#34;  29   &#34;       ##STR66##             CH.sub.2 CH.sub.2 OCH.sub.3                           ##STR67##  deep red                                            509  30   &#34;       ##STR68##              ##STR69##   N[C.sub.3 H.sub.7 (i)].sub.2                                      &#34;     508  31    ##STR70##       ##STR71##             C.sub.5 H.sub.11 (n)                           ##STR72##  red   506  32   &#34;       &#34;      &#34;            N(C.sub.2 H.sub.5).sub.2                                      &#34;     &#34;  33   &#34;       ##STR73##             CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OH                          N(C.sub.2 H.sub.4 CN).sub.2                                      red-brown                                            512  34    ##STR74##       ##STR75##             &#34;            N[C.sub.6 H.sub.13 (sec)].sub.2                                      deep red                                            509  35   &#34;       ##STR76##             CH.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                          N(C.sub.2 H.sub.4 OH).sub.2                                      &#34;     510  36   &#34;       ##STR77##             C.sub.3 H.sub.7 (n)                          N(C.sub.2 H.sub.5).sub.2                                      &#34;     &#34;__________________________________________________________________________ 
    
     
                                           TABLE 3__________________________________________________________________________ ##STR78## No. ##STR79##        ##STR80##                X            Z                Dyed ClothHue                                                     (nm)(acetone).la                                                    mbda.max__________________________________________________________________________37 ##STR81##        ##STR82##               (CH.sub.2).sub.3 O(C.sub.2 H.sub.4 O).sub.2 CH.sub.3                             ##STR83##       red    505  38 ##STR84##        ##STR85##               C.sub.4 H.sub.9 (i)                            NHCH.sub.3         &#34;    507  39 ##STR86##        ##STR87##                ##STR88##                             ##STR89##       deep red                                                    511  40 ##STR90##        ##STR91##                ##STR92##   N[C.sub.3 H.sub.7 (n)].sub.2                                             red    505  41 ##STR93##         &#34;     C.sub.3 H.sub.6 OCH.sub.3                            NH(CH.sub.2).sub.8 CHCH(CH.sub.2).sub.7                            CH.sub.3           &#34;    504__________________________________________________________________________ 
    
     
                                           TABLE 4__________________________________________________________________________ ##STR94## No.    ##STR95##       ##STR96##             X          Z           Dyed ClothHue of                                          (nm)(acetone)λmax__________________________________________________________________________42    ##STR97##       ##STR98##            C.sub.2 H.sub.4 OC.sub.2 H.sub.5                       N[C.sub.9 H.sub.19 (n)].sub.2                                   red   506  43    ##STR99##        &#34;     &#34;                        ##STR100##   &#34;    &#34;  44    ##STR101##       ##STR102##              &#34;        N[C.sub.3 H.sub.7 (i)].sub.2                                   deep red                                         510  45    ##STR103##       ##STR104##              &#34;        N[C.sub.4 H.sub.9 (n)].sub.2                                   red   507  46    ##STR105##       ##STR106##            C.sub.6 H.sub.13 (n)                       N[C.sub.4 H.sub.9 (sec)].sub.2                                   red   506  47    ##STR107##       ##STR108##             (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OH                        ##STR109## deep red                                         512__________________________________________________________________________ 
    
     
                                           TABLE 5__________________________________________________________________________ ##STR110## No.    ##STR111##      ##STR112##              X          Z             Dyed ClothHue                                             (nm)(acetone)λmax__________________________________________________________________________48    ##STR113##      ##STR114##              ##STR115##                         ##STR116##   red   506  49    ##STR117##      ##STR118##             &#34;                         ##STR119##   deep red                                            510  50    ##STR120##      ##STR121##             CH.sub.2 CH.sub.2 OC.sub.3 H.sub.7 (i)                         ##STR122##   &#34;     511  51    ##STR123##     &#34;       &#34;                         ##STR124##   red   505__________________________________________________________________________ 
    
     
                                           TABLE 6__________________________________________________________________________ ##STR125## No.    ##STR126##      ##STR127##             X      Z          Dyed ClothHue of                                     (nm)(acetone)λmax__________________________________________________________________________52    ##STR128##      ##STR129##            (CH.sub.2).sub.5 OH                   NHC.sub.3 H.sub.6 OH                              red   50653    ##STR130##     &#34;      &#34;      N(C.sub.2 H.sub.4 OC.sub.2 H.sub.5).sub.2                              &#34;     &#34;  54    ##STR131##     &#34;      &#34;                    ##STR132##                              deep red                                    511  55    ##STR133##      ##STR134##            C.sub.4 H.sub.9 (sec)                    ##STR135##                              red   506__________________________________________________________________________ 
    
     
                                           TABLE 7__________________________________________________________________________ ##STR136## No.    ##STR137##      ##STR138##            X         Z         Dyed ClothHue of                                        (nm)(acetone)λmax__________________________________________________________________________56    ##STR139##      ##STR140##            ##STR141##                      ##STR142##                               red     506  57    ##STR143##      ##STR144##           CH.sub.2CHCH.sub.2                      ##STR145##                               deep red                                       511  58    ##STR146##      ##STR147##           C.sub.3 H.sub.6 OCH.sub.3                      ##STR148##                               &#34;       509  59    ##STR149##     &#34;     &#34;         N(C.sub.2 H.sub.4 CN).sub.2                               red     504__________________________________________________________________________ 
    
     
                                           TABLE 8__________________________________________________________________________ ##STR150## No.    ##STR151##      ##STR152##             X     Z        Dyed ClothHue of                                  (nm)(acetone)λmax__________________________________________________________________________60    ##STR153##      ##STR154##             ##STR155##                  N(C.sub.2 H.sub.5).sub.2                           red   505  61    ##STR156##     &#34;      CH.sub.3                  NHC.sub.6 H.sub.13 (sec)                           &#34;     &#34;  62    ##STR157##      ##STR158##            &#34;     N[C.sub.3 H.sub.7 (n)].sub.2                           deep red                                 507  63    ##STR159##      ##STR160##            C.sub.3 H.sub.7 (i)                  N(C.sub.2 H.sub.4 OCH.sub.3).sub.2                           red   507  64    ##STR161##     &#34;      C.sub.2 H.sub.4 OH                   ##STR162##                           deep red                                 511__________________________________________________________________________ 
    
     
                                           TABLE 8__________________________________________________________________________ ##STR163## No.    ##STR164##       ##STR165##               X      Z       Dyed ClothHue of                                    (nm)(acetone)λmax__________________________________________________________________________65    ##STR166##       ##STR167##              C.sub.3 H.sub.6 OCH.sub.3                     NHC.sub.3 H.sub.6 OH                             red   507  66    ##STR168##       ##STR169##              &#34;      N[C.sub.3 H.sub.7 (i)].sub.2                             red-brown                                   514  67    ##STR170##       ##STR171##              &#34;      NHC.sub.2 H.sub.4 OH                             deep red                                   511  68    ##STR172##       ##STR173##              C.sub.3 H.sub.6 OCH.sub.3                     N(C.sub.2 H.sub.5).sub.2                             red   506  69    ##STR174##      &#34;       CH.sub.3                      ##STR175##                             deep red                                   511__________________________________________________________________________ 
    
     
                                           TABLE 10__________________________________________________________________________ ##STR176## No.    ##STR177##       ##STR178##             X      Z           Dyed ClothHue of                                      (nm)(acetone)λmax__________________________________________________________________________70    ##STR179##       ##STR180##            C.sub.2 H.sub.4 OH                   N[C.sub.7 H.sub.15 (n)].sub. 2                               deep red                                     513  71    ##STR181##       ##STR182##            (CH.sub.2).sub.6 OH                    ##STR183## red   505  72    ##STR184##      &#34;     &#34;                    ##STR185## &#34;     &#34;  73    ##STR186##      &#34;     (CH.sub.2).sub.2 OH                    ##STR187## &#34;     503  74    ##STR188##      &#34;     C.sub.6 H.sub.13 (n)                   N(C.sub.2 H.sub.4 OCH.sub.3).sub.2                               &#34;     506__________________________________________________________________________ 
    
     
                                           TABLE 11__________________________________________________________________________ ##STR189## No.    ##STR190##       ##STR191##             X         Z            Dyed ClothHue of                                          (nm)(acetone)λmax__________________________________________________________________________75    ##STR192##       ##STR193##            (CH.sub.2).sub.3 OH                       ##STR194##  red   505  76   &#34;       ##STR195##            C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                      N(C.sub.3 H.sub.6 CN).sub.2                                   deep red                                         509  77    ##STR196##       ##STR197##             ##STR198##                      N(C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3).s                      ub.2         red   504  78    ##STR199##       ##STR200##            H                       ##STR201##  &#34;     506  79    ##STR202##       ##STR203##            C.sub.3 H.sub.7 (i)                      N(CH.sub.3).sub.2                                   &#34;     504__________________________________________________________________________ 
    
     
                                           TABLE 12__________________________________________________________________________ ##STR204## No.    ##STR205##      ##STR206##             X         Z       Dyed ClothHue of                                     (nm)(acetone)λmax__________________________________________________________________________80    ##STR207##      ##STR208##            CH.sub.2CHCH.sub.2                       ##STR209##                              red   507  81   &#34;      ##STR210##            (CH.sub.2).sub.4 OH                      NHC.sub.7 H.sub.15 (n)                              &#34;     505  82    ##STR211##     &#34;      C.sub.3 H.sub.6 OC.sub.3 H.sub.7 (i)                      NHC.sub.3 H.sub.7 (i)                              &#34;     &#34;83    ##STR212##      ##STR213##            C.sub.4 H.sub.9 (i)                      N[C.sub.4 H.sub.9 (i)].sub.2                              deep red                                    513__________________________________________________________________________ 
    
     
                                           TABLE 13__________________________________________________________________________ ##STR214## No.    ##STR215##       ##STR216##              X          Z       Dyed ClothHue of                                       (nm)(acetone)λmax__________________________________________________________________________84    ##STR217##       ##STR218##             (CH.sub.2).sub.5 OH                        NHCH.sub.3                                deep red                                      51185    ##STR219##       ##STR220##             C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3                        N[C.sub.4 H.sub.9 (n)].sub.2                                &#34;     509  86    ##STR221##       ##STR222##             &#34;                         ##STR223##                                red   507  87    ##STR224##       ##STR225##             H          NH.sub.2                                &#34;     506__________________________________________________________________________ 
    
     
                                           TABLE 14__________________________________________________________________________ ##STR226## No.    ##STR227##       ##STR228##              X       Z            Dyed ClothHue of                                          (nm)(acetone)λmax__________________________________________________________________________88    ##STR229##       ##STR230##              ##STR231##                     N[C.sub.3 H.sub.7 (n)].sub.2                                  red    505  89    ##STR232##       ##STR233##             C.sub.2 H.sub.4 OC.sub.2 H.sub.5                      ##STR234##  deep red                                         511  90    ##STR235##       ##STR236##             C.sub.3 H.sub.6 OH(n)                     N(C.sub.2 H.sub.5).sub.2                                  red    505__________________________________________________________________________ 
    
     
                                           TABLE 15__________________________________________________________________________ ##STR237## No.D                      m                         Z                                  ##STR238##                                         (T/C mixed cloth)Hue of Dye                                        Cloth      (acetone)                                                  (nm)λmax__________________________________________________________________________91##STR239##            2 OC.sub.2 H.sub.4 OC.sub.2 H.sub.5                                  ##STR240##                                        red-brown 483  92##STR241##            &#34; OCH.sub.3                                  ##STR242##                                        red       485  93    &#34;                      3 OC.sub.2 H.sub.5                                  ##STR243##                                         &#34;        487  94##STR244##            2                         ##STR245##                                  ##STR246##                                        bluish red                                                  512  95    &#34;                      &#34; OCH.sub.3                                  ##STR247##                                         &#34;         &#34;  96##STR248##            &#34; OC.sub.3 H.sub.7 (n)                                  ##STR249##                                        orange    470  97    &#34;                      3   &#34;                                  ##STR250##                                         &#34;        472  98##STR251##            2 OC.sub.2 H.sub.4 OCH.sub.3                                  ##STR252##                                        gold      469  99##STR253##            &#34; OC.sub.3 H.sub.6 OC.sub.2 H.sub.5                                 &#34;       &#34;        461   100##STR254##            &#34; OC.sub.2 H.sub.5                                  ##STR255##                                        yellowish red                                                  489  101    &#34;                      3 OC.sub.4 H.sub.9 (t)                                  ##STR256##                                         &#34;         &#34;   102##STR257##            2 OCH.sub.3                                  ##STR258##                                         &#34;        499  103##STR259##            &#34;   &#34;                                  ##STR260##                                        red       501  104##STR261##            &#34; OC.sub.2 H.sub.5                                  ##STR262##                                         &#34;        503   105    &#34;                      3                         ##STR263##                                 &#34;       &#34;        505  106    &#34;                      2 OCH.sub.3                                  ##STR264##                                         &#34;        501  107##STR265##            &#34; OC.sub.3 H.sub.7 (n)                                  ##STR266##                                         &#34;        503  108    &#34;                      &#34; OC.sub.2 H.sub.4 OCH.sub.3                                  ##STR267##                                         &#34;        501   109##STR268##            &#34; OCH.sub.3                                  ##STR269##                                        deep red  505  110##STR270##            &#34;                         ##STR271##                                 &#34;       &#34;         &#34;  111    &#34;                      &#34; OC.sub.4 H.sub.9 (sec)                                  ##STR272##                                         &#34;        503  112##STR273##            &#34; OC.sub.3 H.sub.7 (i)                                  ##STR274##                                         &#34;        507  113    &#34;                      3 OCH.sub.3                                 &#34;       &#34;        508  114##STR275##            2 OC.sub.2 H.sub.5                                 &#34;       &#34;        505  115    &#34;                      3 OC.sub.2 H.sub.4 OCH.sub.3                                  ##STR276##                                         &#34;        506  116##STR277##            2 OC.sub.5 H.sub.11 (n)                                  ##STR278##                                         &#34;        507  117##STR279##            &#34; OC.sub.4 H.sub.9 (t)                                  ##STR280##                                         &#34;         &#34;  118    &#34;                      &#34;                         ##STR281##                                 &#34;       &#34;         &#34;  119    &#34;                      3 OC.sub.2 H.sub.4 OC.sub.2 H.sub.5                                  ##STR282##                                         &#34;        508  120##STR283##            2 OC.sub.3 H.sub.6 OCH.sub.3                                  ##STR284##                                          &#34;       506  121##STR285##            3 OCH.sub.3                                  ##STR286##                                         &#34;        509  122##STR287##            2 OC.sub.2 H.sub.5                                  ##STR288##                                        orange    468  123##STR289##            &#34; OC.sub.3 H.sub.7                                  ##STR290##                                         &#34;         &#34;  124##STR291##            &#34; OC.sub.2 H.sub.5                                  ##STR292##                                        red       494  125    &#34;                      &#34;   &#34;                                  ##STR293##                                         &#34;        492  126##STR294##            &#34; OC.sub.5 H.sub.11 (sec)                                  ##STR295##                                        reddish blue                                                  594  127    &#34;                      3 OC.sub.2 H.sub.5                                 &#34;       &#34;        595  128    &#34;                      2 OC.sub.3 H.sub.7 (i)                                  ##STR296##                                         &#34;        592   129    &#34;                      3 OC.sub.4 H.sub.9 (sec)                                  ##STR297##                                         &#34;        593__________________________________________________________________________ 
    
     EXAMPLE 7 
     A dye composition consisting of 15 parts of a disazo dye represented by the formula: ##STR298## 15 parts of a naphthalenesulfonic acid-formaldehyde condensate, and 70 parts of water was finely dispersed by the use of a paint shaker as a finely dispersing apparatus to prepare a dye dispersion. This dye dispersion was used to prepare a printing color paste having the following composition: 
     
         ______________________________________                 parts______________________________________Dye dispersion         6.55% Aqueous sodium alginate solution                  55Polyethylene glycol dimethyl ether                  9having an average molecular weightof 400Water                  29.5Total                  100    (pH 8.0)______________________________________ 
    
     The thus-prepared printing color paste was printed on a polyester/cotton mixed cloth (mixing ratio: 65/35) by the use of a screen printer, was subjected to intermediate drying at 80° C. for 3 minutes, and was fixed by dry heating at 215° C. for 90 seconds. The cloth was then washed with water and was subjected to soaping using a cleaning liquid containing 2 g/l of a nonionic surface active agent (Scorerol #900 (trade name), produced by Kao Sekken Co., Ltd.) at 80° C. for 20 minutes at a bath ratio of 1:30. There was thus obtained a product dyed in yellowish red having excellent light fastness and wet color fastness. 
     The dye used in this example was prepared as follows. 
     In accordance with the usual method, 4-aminoazobenzene was diazotized and coupled with 2(m-hydroxy)anilino-3-cyano-4-methyl-6-(Υ-methoxypropylamino)pyridine to prepare a dye. A mixture of 5.07 g of the above-prepared dye, 2.1 g of 2,4-difluoro-6-(diethyl)aminotriazine, and 1.0 g of anhydrous potassium carbonate was added to 100 ml of acetone and heated at reflux to achieve a condensation reaction. The resulting reaction solution was added dropwise to 1,000 ml of water. The precipitate thus obtained was separated by filtration, washed with water, and dried at room temperature to obtain 6.5 g of red powder of the dye represented by the above-described formula. For this dye, λmax (acetone was 490 nm. 
     EXAMPLE 8 
     A dye composition consisting of 15 parts of a disazo dye represented by the formula: ##STR299## 10 parts of a Pluronic surface active agent, Pluronic L64 (trade name, produced by Asahi Denka Kogyo Co., Ltd.), and 7.5 parts of water was finely dispersed by the use of a sand grinder as a finely dispersing apparatus to prepare a dye. This dye was used to prepare a printing color paste having the following composition: 
     
         ______________________________________                 parts______________________________________Dye dispersion         75% Aqueous sodium alginate solution                  55Diacetate of polypropylene glycol                  10having an average molecular weightof 300Polyethylene glycol diglycidyl ether                  3having an average molecular weightof 200Water                  25Total                  100    (pH: 6.5)______________________________________ 
    
     The above-prepared printing color paste was printed on a cotton broad (cotton yarn number: 40) which had been subjected to silket processing, by the use of a screen printing machine, was subjected to intermediate drying at 80° C. for 3 minutes, and was treated with super heated steam at 185° C. for 7 minutes. Thereafter, a cleaning processing was performed in the same manner as in Example 7, and there was thus obtained a product dyed in reddish brown having excellent light fastness and wet color fastness. 
     The dye used in this example was prepared as follows. 
     In accordance with the usual method, 1-aminoanthraquinone was diazotized and coupled with 2-(p-hydroxy)anilino-3-cyano-4-methyl-6-(β-hydroxyethylamino)pyridine to prepare a dye. The dye thus formed was then reacted with 2,4-difluoro-6-[di(n-propyl)amino]triazine in N-methyl-2-pyrrolidone by the use of triethylamine as an acid-removing agent to obtain the desired dye. For this dye, λmax (acetone) was 483 nm. 
     EXAMPLE 9 
     A dye composition consisting of 10 parts of a monoazo dye represented by the formula: ##STR300## 2 parts of polyoxyethylene glycol nonylphenyl ether (HLB: 8.9), and 88 parts of diethylene glycol diacetate was finely dispersed by the use of a paint conditioner as a finely dispersing apparatus to prepare a dye ink. 
     A mixture of 10 parts of the above-prepared dye ink and 55 parts of mineral turpentine was gradually poured into 35 parts of an aqueous solution having the composition as described hereinafter while stirring by a homomixer at 5,000 to 7,000 rpm, and the resulting mixture was stirred until it became uniform to prepare a viscous o/w emulsion type color paste. 
     
         ______________________________________Composition of Aqueous Solution                parts______________________________________Water                  31Repitol G (trade name, special                  3.8nonionic surface active agent,produced by Dai-ichi Kogyo SeiyakuCo., Ltd.)Sodium trichloroacetate                  0.1Total                  34.9______________________________________ 
    
     This color paste was printed on a polyester/cotton mixed cloth (mixing ratio: 65/35) by the use of a screen printing machine, dried at 100° C. for 2 minutes, and treated with super heated steam at 175° C. for 7 minutes. Thereafter, the cloth was washed with a hot tetrachloroethylene bath containing a small amount of water and dried, and there was thus obtained a golden dyed product having excellent light fastness and wet color fastness, and free from contamination in the white background. 
     The dye used in this example was prepared as follows. 
     In accordance with the usual method, 2-chloro-4-methylsulfonylaniline was diazotized and coupled with 2-(p-hydroxyphenylethylamino)-3-cyano-4-methyl-6-ethoxyethylaminopyridine to form a dye. The dye thus formed was reacted with 2,4-difluoro-6-piperidinotriazine in the same manner as in Example 7 to obtain the desired dye. For this dye, λmax (acetone) was 469 nm. 
     EXAMPLE 10 
     A dye composition consisting of 16 parts of a disazo dye represented by the formula: ##STR301## 7 parts of polyoxyethylene glycol nonylphenyl ether (HLB: 13.3), 3 parts of a naphthalenesulfonic acid-formaldehyde condensate, and 74 parts of water was finely dispersed by the use of a sand grinder to prepare a dye dispersion. This dye dispersion was used to prepare a padding bath having the following composition: 
     
         ______________________________________                 parts______________________________________Dye dispersion         6Tetraethylene glycol dimethyl ether                  15Water                  79Total                  100    (pH: 8.0)______________________________________ 
    
     A polyester/cotton mixed cloth (mixing ratio: 65/35) was impregnated with the above-prepared padding bath, squeezed at a squeezing ratio of 45%, dried at 100° C. for 2 minutes, and fixed by dry heating at 200° C. for 1 minute. By washing the cloth with a hot ethanol bath, there was obtained a product dyed in red having excellent light fastness and wet color fastness. 
     The dye used in this example was prepared in the same manner as in Example 7. For this dye, λmax (acetone) was 503 nm. 
     EXAMPLE 11 
     Printing was performed in the same manner as in Example 1 except that a nylon/rayon mixed cloth (mixing ratio: 50/50) was used and the dry heating fixing temperature was 185° C. There was thus obtained a product dyed in red having good light fastness and wet color fastness. 
     EXAMPLE 12 
     Using a series of azo dyes as shown in Tables 16 to 22, printing was performed in the same manner as in Example 7. 
     All dyed clothes had good light fastness and wet color fastness. The hue of each dyed cloth and λmax (acetone) of each dye are shown in Tables 16 to 22. 
     
                                           TABLE 16__________________________________________________________________________ ##STR302##                                                     λmax                                               Hue                                                     (acetone)No.   D                   Z                W           Dyed                                                     (nm)h__________________________________________________________________________    ##STR303##         C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                   N[CH.sub.2 CH.sub.2 N(CH.sub.3).su                                   b.2 ].sub.2 red-orange                                                     472  2   &#34;                   H                                    ##STR304## &#34;     468  3    ##STR305##                   ##STR306##      N(CH.sub.2 CH.sub.2 CH.sub.2                                   OH).sub.2   deep                                                     513  4   &#34;                   CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                    ##STR307## &#34;     &#34;  5    ##STR308##         C.sub.5 H.sub.11 (n)                                    ##STR309## red-orange                                                     476  6    ##STR310##         (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OH                                    ##STR311## reddish yellow                                                     469  7    ##STR312##         CH.sub.2 CH.sub.2 CH.sub.2 OC.sub.3 H.sub.7                                    ##STR313## reddish yellow                                                     470  8    ##STR314##         C.sub.4 H.sub. 9 (sec)                                   NH.sub.2    red   503  9    ##STR315##         (CH.sub.2).sub.5 OH                                   NHC.sub.3 H.sub.7 (i)                                               &#34;     &#34;   10   &#34;                   CH.sub.2 CH.sub.2 OH                                   N[C.sub.4 H.sub.9 (sec)].sub.2                                               &#34;     512  11   &#34;                   (CH.sub.2).sub.3 O(C.sub.2 H.sub.4 O).sub.2                  CH.sub.3                                    ##STR316## &#34;     513  12    ##STR317##                   ##STR318##                                    ##STR319## orange                                                     469  13    ##STR320##         C.sub.4 H.sub.9 (i)                                    ##STR321## &#34;     &#34;  14   &#34;                   C.sub.5 H.sub.11 (sec)                                    ##STR322## red   493  15   &#34;                   (CH.sub.2).sub.2 O(CH.sub.2).sub.2 OH                                   NHC.sub.5 H.sub.11 (i)                                               &#34;     &#34;  16    ##STR323##         CH.sub.2 CH.sub.2 CH.sub.2 OH                                    ##STR324## reddish blue                                                     593  17   &#34;                   ##STR325##      N(C.sub.2 H.sub.5).sub.2                                               reddish blue                                                     &#34;__________________________________________________________________________ 
    
     
                                           TABLE 17__________________________________________________________________________ ##STR326##                                                     λmax                                               Hue                                                     (acetone)No.   D                     Z            W             Dyed                                                     (nm)h__________________________________________________________________________18    ##STR327##           CH.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                  ##STR328##   reddish yellow                                                     471  19   &#34;                     C.sub.2 H.sub.5                                  ##STR329##   reddish yellow                                                     &#34;  20    ##STR330##           (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OC.sub.2                    H.sub.5      N(CH.sub.2 CH.sub.2 OCH.sub.3).sub.2                                               bluish                                                     513  21   &#34;                     ##STR331##                                  ##STR332##   &#34;     514  22    ##STR333##           C.sub.3 H.sub.7 (i)                                 N(CH.sub.3).sub.2                                               yellowish red                                                     487  23   &#34;                     CH.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                 NH.sub.2      yellowish                                                     486                                               red  24    ##STR334##           C.sub.5 H.sub.11 (sec)                                  ##STR335##   red   492  25    ##STR336##           CH.sub.2 CH.sub.2 OH                                  ##STR337##   &#34;     501  26    ##STR338##           CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OH                                 N[C.sub.3 H.sub.7 (i)].sub.2                                               &#34;     502  27    ##STR339##           CH.sub.2 CH.sub.2 CH.sub.2 OH                                  ##STR340##   reddish yellow                                                     470  28    ##STR341##           H                                  ##STR342##   reddish orange                                                     478  29    ##STR343##                     ##STR344##  N(C.sub.2 H.sub.4 OC.sub.2 H.sub.4                                 OCH.sub.3).sub.2                                               red   502  30    ##STR345##           CH.sub.2 CH.sub.2 OCH.sub.3                                  ##STR346##   yellowish red                                                     494  31    ##STR347##           (CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH                                  ##STR348##   red   503  32    ##STR349##                     ##STR350##  N[C.sub.4 H.sub.9 (sec)].sub.2                                               &#34;     500  33    ##STR351##           C.sub.5 H.sub.11 (n)                                 N(CH.sub.2CHCH.sub.2).sub.2                                               orange                                                     473  34    ##STR352##           C.sub.2 H.sub.4 OH                                 N[C.sub.3 H.sub.7 (i)].sub.2                                               red   492__________________________________________________________________________ 
    
     
                                           TABLE 18__________________________________________________________________________ ##STR353##                                                     λmax                                               Hue                                                     (acetone)No.   D                  Z            W                Dyed                                                     (nm)h__________________________________________________________________________35    ##STR354##        C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3                              NHC.sub.2 H.sub.4 OH                                               yellow                                                     461  36    ##STR355##                  ##STR356##  NHC.sub.5 H.sub.11 (n)                                               bluish red                                                     513  37    ##STR357##        C.sub.4 H.sub.9 (i)                              N[C.sub.6 H.sub.13 (n)].sub.2                                               bluish red                                                     514  38    ##STR358##        C.sub.2 H.sub.4 OH                              NH(CH.sub.2).sub.8 CHCH(CH.sub.2).sub.7                               CH.sub.3        bluish red                                                     512  39    ##STR359##        CH.sub.3     N[C.sub.9 H.sub.19 (n)].sub.2                                               orange                                                     469  40    ##STR360##        C.sub.2 H.sub.4 OCH.sub.3                              N(C.sub.2 H.sub.4 OCH.sub.3).sub.2                                               red-brown                                                     486  41    ##STR361##        C.sub.2 H.sub.4 OC.sub.2 H.sub.5                              N[C.sub.3 H.sub.7 (n)].sub.2                                               reddish  blue                                                     592__________________________________________________________________________ 
    
     
                                           TABLE 19__________________________________________________________________________ ##STR362##                                          λmax                                    Hue of                                          (acetone)No.   D-             Z         W            Dyed Cloth                                          (nm)__________________________________________________________________________42    ##STR363##    CH.sub.2 CH.sub.2 CH.sub.2 OH                        ##STR364##  yellowish red                                          495  43    ##STR365##    &#34;                        ##STR366##  orange                                          465  44    ##STR367##    &#34;         N(C.sub.2 H.sub.4 CN).sub.2                                    bluish red                                          513  45    ##STR368##    CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                       N[C.sub.5 H.sub.11 (i)].sub.2                                    yellowish red                                          491  46    ##STR369##    &#34;                        ##STR370##  red   510  47    ##STR371##    CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                       NH.sub.2     bluish red                                          523  48    ##STR372##    C.sub.4 H.sub.9 (n)                       NHC.sub.18 H.sub.37 (n)                                    orange                                          472__________________________________________________________________________ 
    
     
                                           TABLE 20__________________________________________________________________________ ##STR373##                                         λmax                                   Hue of                                         (acetone)No.   D            Z          W            Dyed Cloth                                         (nm)__________________________________________________________________________49    ##STR374##            ##STR375##                      N[C.sub.3 H.sub.7 (i)].sub.2                                   yellowish red                                         489  50    ##STR376##  &#34;          N[C.sub.4 H.sub.9 (n)].sub.2                                   red-brown                                         487  51    ##STR377##  &#34;          NHC.sub.7 H.sub.15 (sec)                                   orange                                         465  52    ##STR378##  CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                       ##STR379##  red-orange                                         479  53    ##STR380##  &#34;          N(C.sub.2 H.sub.4 OCH.sub.3).sub.2                                   yellowish red                                         491  54    ##STR381##  C.sub.3 H.sub.7 (i)                      N(C.sub.2 H.sub.4 OH).sub.2                                   red   505  55    ##STR382##  C.sub.2 H.sub.4 OH                       ##STR383##  deep red                                         511__________________________________________________________________________ 
    
     
                                           TABLE 21__________________________________________________________________________ ##STR384##                                              λmax                                        Hue of                                              (acetone)No.   D                Z            W           Dyed Cloth                                              (nm)__________________________________________________________________________56    ##STR385##                ##STR386##                             ##STR387## bluish red                                              514  57    ##STR388##      &#34;            NHC.sub.14 H.sub.29 (sec)                                        reddish yellow                                              469  58    ##STR389##      CH.sub.2 CH.sub.2 CH.sub.2 OC.sub.3 H.sub.7 (i)                             ##STR390## orange                                              471  59    ##STR391##      &#34;                             ##STR392## red   492  60    ##STR393##      CH.sub.2 CH.sub.2 CH.sub.2 OC.sub.3 H.sub.7 (i)                            N(CH.sub.2CHCH.sub.2).sub.2                                         &#34;    501  61    ##STR394##      C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.2 H.sub.5                            NHC.sub.2 H.sub.5                                         &#34;    &#34;  62    ##STR395##      &#34;            N[C.sub.3 H.sub.7 (i)].sub.2                                         &#34;    504__________________________________________________________________________ 
    
     
                                           TABLE 22__________________________________________________________________________ ##STR396##                                              λmax                                        Hue of                                              (acetone)No.   D                   Z          W          Dyed Cloth                                              (nm)__________________________________________________________________________63    ##STR397##                   ##STR398##                              ##STR399##                                        red   505  64    ##STR400##         &#34;                              ##STR401##                                        reddish orange                                              479  65    ##STR402##         C.sub.6 H.sub.13 (i)                             N[C.sub.3 H.sub.7 (n)].sub.2                                        yellowish red                                              491  66    ##STR403##         &#34;          N[C.sub.7 H.sub.15 (n)].sub.2                                        bluish red                                              518  67    ##STR404##         CH.sub.2 CH.sub.2 OC.sub.2 H.sub.4 OH                              ##STR405##                                        orange                                              466  68    ##STR406##         &#34;                              ##STR407##                                        red   493__________________________________________________________________________ 
    
     EXAMPLE 13 
     A dye composition consisting of 15 parts of a disazo dye represented by the formula: ##STR408## 15 parts of a naphthalenesulfonic acid-formaldehyde condensate, and 70 parts of water was finely dispersed by the use of a paint shaker as finely dispersing apparatus to prepare a dye dispersion. This dye dispersion was used to prepare a printing color paste having the following composition: 
     
         ______________________________________                 parts______________________________________Dye dispersion         6.55% Aqueous sodium alginate solution                  55Polyethylene glycol dimethyl ether                  9having an average molecular weightof 400Water                  29.5Total                  100    (pH 8.0)______________________________________ 
    
     The thus prepared printing color paste was printed on a polyester/cotton mixed cloth (mixing ratio: 65/35) by the use of a screen printing machine, was subjected to intermediate drying at 80° C. for 3 minutes, and was fixed by dry heating at 125° C. for 90 seconds. The cloth was then washed with water, and was subjected to soaping using a cleaning liquid containing 2 g/l of a nonionic surface active agent (Scorerol #900 (trade name), produced by Kao Sekken Co., Ltd.) at 80° C. for 20 minutes at a bath ratio of 1:30. There was thus obtained a product dyed in yellowish red having excellent light fastness and wet color fastness. 
     The dye used in this example was prepared as follows. 
     In accordance with the usual method, 4-aminoazobenzene was diazotized and coupled with 2-(γ-methoxypropylamino)-3-cyano-4-methyl-6-(m-hydroxyanilino)pyridine to form a dye. A mixture of 5.07 g of the above prepared dye, 2.1 g of 2,4-difluoro-6-(diethyl)aminotriazine, 1.0 g of triethylamine, and 1.0 g of anhydrous potassium carbonate was added to 100 ml of acetone and heated at reflux for 3 hours to achieve a condensation reaction. The reaction solution was then added dropwise to 1,000 ml of water, and the precipitate thus formed was separated by filtration, washed with water, and dried at room temperature to obtain 6.4 g of red powder of the dye represented by the above described formula. For this dye, λmax (acetone) was 490 nm. 
     EXAMPLE 14 
     A dye composition consisting of 15 parts of a monoazo dye represented by the formula: ##STR409## 10 parts of a Pluronic surface active agent, Pluronic L64 (trade name, produced by Asahi Denka Kogyo Co., (Ltd.), and 75 parts of water was finely dispersed by the use of a sand grinder as a finely dispersing apparatus to prepare a dye dispersion. This dye dispersion was used to prepare a printing color paste having the following composition: 
     
         ______________________________________                 parts______________________________________Dye dispersion         75% Aqueous sodium alginate solution                  55Diacetate of polypropylene glycol                  10having an average molecular weightof 300Polyethylene glycol diglycidyl ether                  3having an average molecular weightof 200Water                  25Total                  100    (pH: 6.5)______________________________________ 
    
     The thus prepared printing color paste was printed on a cotton broad (cotton yarn number: 40) which had been subjected to silket processing, by the use of a screen printing machine, was subjected to intermediate drying at 80° C. for 3 minutes, and was treated using super heated steam at 185° C. for 7 minutes. 
     Thereafter, a washing processing was performed in the same manner as in Example 13, and there was thus obtained a product dyed in reddish brown having excellent light fastness and wet color fastness. 
     The dye used in this example was prepared as follows. 
     In accordance with the usual method, 1-aminoanthraquinone was diazotized and coupled with 2-anilino-3-cyano-4-methyl-6-(4-hydroxybenzylamino)pyridine to form a dye. The dye thus formed was reacted with 2,4-difluoro-6-(N,N-diisopropylamino)triazine in N-methyl-2-pyrrolidone by the use of triethylamine as an acid-removing agent to obtain the desired dye. For this dye, λmax (acetone) was 484 nm. 
     EXAMPLE 15 
     A dye composition consisting of 10 parts of a monoazo dye represented by the formula: ##STR410## 2 parts of polyoxyethylene glycol nonylphenyl ether (HLB: 8.9), and 88 parts of diethylene glycol diacetate was ground by the use of a paint conditioner as a finely dispersing apparatus to prepare a dye ink. 
     A mixture of 10 parts of the above prepared dye ink and 55 parts of mineral turpentine was gradually poured into 35 parts of an aqueous solution having the composition as described hereinafter while stirring by a homomixer at 5,000 to 7,000 rpm, and the resulting mixture was then stirred until it became uniform to obtain a viscous o/w emulsion color paste. 
     
         ______________________________________Composition of Aqueous Solution                parts______________________________________Water                  31Repitol G (trade name, special                  3.8nonionic surface active agent,produced by Dai-ichi Kogyo SeiyakuCo., Ltd.)Sodium trichloroacetate                  0.1Total                  34.9______________________________________ 
    
     The thus prepared color paste was printed on a polyester/cotton mixed cloth (mixing ratio: 65/35) by the use of a screen printing machine, dried at 100° C. for 2 minutes, and treated with super heated steam at 175° C. for 7 minutes. The cloth was washed with a hot tetrachloroethylene bath containing a small amount of water and dried, and there was thus obtained a golden dyed product having excellent light fastness and wet color fastness, and free from contamination in the white background. 
     The dye used in this example was prepared as follows. 
     In accordance with the usual method, 2-chloro-4-methylsulfonylaniline was diazotized and coupled with 2-amino-3-cyano-4-methyl-6-(p-hydroxyanilino)pyridine to form a dye. The dye thus formed was reacted at reflux with 2,4-dichloro-6-(n)-hexylaminotriazine in dioxane in the presence of tri-n-butylamine as an acid-removing agent for 3 hours. At the end of the time, the reaction solution was cooled, and crystals separated were collected by filtration to obtain the desired dye. For this dye, λmax (acetone) was 467 nm. 
     EXAMPLE 16 
     A dye composition consisting of 16 parts of a disazo dye represented by the formula: ##STR411## 7 parts of polyoxyethylene glycol nonylphenyl ether (HLB: 13.3), 3 parts of a naphthalenesulfonic acid-formaldehyde condensate, and 74 parts of water was finely dispersed by the use of a sand grinder to prepare a dye dispersion. This dye was used to prepare a padding bath having the following composition: 
     
         ______________________________________                 parts______________________________________Dye dispersion         6Tetraethylene glycol dimethyl ether                  15Water                  79Total                  100    (pH: 8.0)______________________________________ 
    
     A polyester/cotton mixed cloth (mixing ratio: 65/35) was impregnated with the above prepared padding bath, squeezed at a squeezing ratio of 45%, dried at 100° C. for 2 minutes, and fixed by dry heating at 200° C. for 1 minute. The cloth was washed with a hot ethanol bath, and there was thus obtained a product dyed in red having excellent light fastness and wet color fastness. 
     The dye used in this example was prepared according to the method as described in Example 13. For this dye, λmax (acetone) was 503 nm. 
     EXAMPLE 17 
     Printing was performed in the same manner as in Example 13 except that a nylon/rayon mixed cloth (mixing ratio: 50/50) was employed and the dry heating fixing temperature was 185° C. There was obtained a product dyed in red having good light fastness and wet color fastness. 
     EXAMPLE 18 
     Using a series of azo dyes as shown in Tables 23 to 30, printing was performed in the same manner as in Example 13. 
     All dyed clothes had good light fastness and wet color fastness. The hue of each dyed cloth and λmax (acetone) of each dye are shown in Tables 23 to 30. 
     
                                           TABLE 23__________________________________________________________________________ ##STR412##                                                      λmax                                                      (ace-                                                Hue                                                      tone)No.   D                   Z                 W           Dyed                                                      (nm)h__________________________________________________________________________ 1    ##STR413##         H                 N(C.sub.2 H.sub.5).sub.2                                                red                                                      473nge   2   &#34;                   ##STR414##       NHC.sub.2 H.sub.4 OH                                                &#34;     474   3   &#34;                   C.sub.2 H.sub.4 OCH.sub.3                                     ##STR415## &#34;     &#34;   4    ##STR416##         CH.sub.2CHCH.sub.2                                     ##STR417## deep                                                      514   5   &#34;                   ##STR418##       N[C.sub.3 H.sub.7 (i)].sub.2                                                &#34;     &#34;   6    ##STR419##         C.sub.3 H.sub.7 (n)                                     ##STR420## deep                                                      514   7    ##STR421##         C.sub.3 H.sub.6 OCH.sub.3                                     ##STR422## orange                                                      477   8   &#34;                   C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3                                    N(C.sub.2 H.sub.4 OCH.sub.3).sub.                                    2           &#34;     &#34;   9    ##STR423##         C.sub.3 H.sub.6 OC.sub.2 H.sub.4                                     ##STR424## reddish yellow                                                      470  10    ##STR425##         C.sub.4 H.sub.9 (n)                                    N(CH.sub.2CHCH.sub.2).sub.2                                                gold  471  11    ##STR426##         C.sub.3 H.sub.6 OC.sub.3 H.sub.7 (i)                                     ##STR427## red   504  12    ##STR428##         C.sub.2 H.sub.4 OH                                    N(C.sub.2 H.sub.4 CN).sub.2                                                red   504  13    ##STR429##         C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                     ##STR430## &#34;     503  14    ##STR431##         &#34;                 NHC.sub.3 H.sub.7 (i)                                                deep                                                      519  15    ##STR432##         C.sub.3 H.sub.6 OH                                    N(n-C.sub.3 H.sub.7).sub.2                                                orange                                                      471  16   &#34;                   ##STR433##       N(i-C.sub.3 H.sub.7).sub.2                                                &#34;     &#34;  17    ##STR434##         C.sub.4 H.sub.9 (i)                                    NHC.sub.6 H.sub.13 (sec)                                                red   495  18    ##STR435##                   ##STR436##       NH.sub.2     reddish blue                                                      595  19   &#34;                   C.sub.4 H.sub.8 OH                                    N(C.sub.2 H.sub.5).sub.2                                                &#34;     &#34;__________________________________________________________________________ 
    
     
                                           TABLE 24__________________________________________________________________________ ##STR437##                                                   λmax                                             Hue of                                                   (acetone)No.  D                     Z          W           Dyed Cloth                                                   (nm)__________________________________________________________________________20 ##STR438##           C.sub.2 H.sub.4 OH                                  ##STR439## red orange                                                   473  21 ##STR440##           C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.2                      H.sub.5    N(C.sub.2 H.sub.4 CN).sub.2                                             yellowish red                                                   489  22 &#34;                     H                                  ##STR441## yellowish red                                                   &#34;  23 ##STR442##                       ##STR443##                                  ##STR444## reddish yellow                                                   472  24 ##STR445##           C.sub.6 H.sub.13 (n)                                  ##STR446## red-brown                                                   490  25 ##STR447##                       ##STR448##                                  ##STR449## bluish                                                   517  26 ##STR450##           C.sub.5 H.sub.11 (n)                                  ##STR451## red   502  27 ##STR452##           C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                 N(CH.sub.3).sub.2                                             yellow                                                   464  28 ##STR453##                       ##STR454##                                  ##STR455## red   509  29 ##STR456##           C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                 N[C.sub.4 H.sub.9 (sec)].sub.2                                             yellowish red                                                   495  30 ##STR457##           &#34;                                  ##STR458## yellowish red                                                   494  31 ##STR459##           C.sub.2 H.sub.5                                 &#34;           deep red                                                   503  32 &#34;                     C.sub.3 H.sub.6 OC.sub.3 H.sub.7                                  ##STR460## deep red                                                   &#34;  33 ##STR461##           C.sub.3 H.sub.6 OH                                 NHC.sub.7 H.sub.15 (n)                                             deep red                                                   510  34 ##STR462##           C.sub.4 H.sub.8 OH                                 N(C.sub.2 H.sub.4 OCH.sub.3).sub.2                                             deep red                                                   510  35 ##STR463##           H          N(C.sub.9 H.sub.19).sub.2                                             orange                                                   475  36 ##STR464##           CH.sub.2CHCH.sub.2                                  N(CH.sub.2CHCH.sub.2).sub.2                                             red-brown                                                   488__________________________________________________________________________ 
    
     
                                           TABLE 25__________________________________________________________________________ ##STR465##                                            λmax                                      Hue of                                            (acetone)No.   D                 Z       W             Dyed Cloth                                            (nm)__________________________________________________________________________37    ##STR466##       C.sub.2 H.sub.4 OH                        N[C.sub.3 H.sub.6 N(CH.sub.3).sub.2 ].sub.2                                      orange                                            473  38    ##STR467##       &#34;                         ##STR468##   yellow                                            463  39    ##STR469##       &#34;                         ##STR470##   red-brown                                            491  40    ##STR471##       C.sub.2 H.sub.4 OC.sub.2 H.sub.5                        N(CH.sub.2CHCH.sub.2).sub.2                                      red   503  41    ##STR472##       CH.sub.3                         ##STR473##     &#34;   506  42    ##STR474##       C.sub.3 H.sub.6 OH                         ##STR475##     &#34;   494  43    ##STR476##       C.sub.3 H.sub.7 (i)                         ##STR477##   reddish  blue                                            595__________________________________________________________________________ 
    
     
                                           TABLE 26__________________________________________________________________________ ##STR478##                                            λmax                                      Hue of                                            (acetone)No.   D                Z         W            Dyed Cloth                                            (nm)__________________________________________________________________________44    ##STR479##      C.sub.4 H.sub.9 (i)                          ##STR480##  yellowish red                                            488  45    ##STR481##      H                          ##STR482##  orange                                            478  46    ##STR483##      C.sub.2 H.sub.4 OCH.sub.3                         N(C.sub.2 H.sub.5).sub.2                                      red   504  47    ##STR484##      CH.sub.2CHCH.sub.2                         N[C.sub.3 H.sub.7 (i)].sub.2                                      red   508  48    ##STR485##      C.sub.3 H.sub.6 OCH.sub.3                         N[C.sub.5 H.sub.11 (n)].sub.2                                      red   510  49    ##STR486##                ##STR487##                          ##STR488##  bluish red                                            524  50    ##STR489##      C.sub.2 H.sub.4 OC.sub.3 H.sub.7 (i)                          ##STR490##  orange                                            471__________________________________________________________________________ 
    
     
                                           TABLE 27__________________________________________________________________________ ##STR491##                                                    λmax                                              Hue of                                                    (acetone)No.   D                  Z          W                 Dyed                                                    (nm)h__________________________________________________________________________51    ##STR492##        C.sub.2 H.sub.4 OC.sub.3 H.sub.7                            N[C.sub.9 H.sub.19 (n)].sub.2                                              deep                                                    514  52    ##STR493##                  ##STR494##                            N(CH.sub.2 CH.sub.2 CH.sub.2 OH).sub.2                                              red-brown                                                    488  53    ##STR495##                  ##STR496##                            NH(CH.sub.2).sub.8 CHCH(CH.sub.2).sub.7                            CH.sub.3          yellow                                                    462  54    ##STR497##        C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                             ##STR498##       red   507  55    ##STR499##        CH.sub.2CHCH.sub.2                            N[C.sub.3 H.sub.7 (n)].sub.2                                              red   508  56    ##STR500##                  ##STR501##                             ##STR502##       red   493  57    ##STR503##        C.sub.3 H.sub.6 OH                            N[C.sub.4 H.sub.9 (n)].sub.2                                              red   508  58    ##STR504##        C.sub.3 H.sub.6 OH                            NH.sub.2          deep                                                    510__________________________________________________________________________ 
    
     
                                           TABLE 28__________________________________________________________________________ ##STR505##                                          λmax                                    Hue of                                          (acetone)No.   D                 Z       W           Dyed Cloth                                          (nm)__________________________________________________________________________59    ##STR506##       C.sub.6 H.sub.13 (n)                         ##STR507## red   502  60    ##STR508##       C.sub.2 H.sub. 4 OH                        N(CH.sub.2CHCH.sub.2).sub.2                                    &#34;     505  61    ##STR509##                 ##STR510##                        N(C.sub.2 H.sub.5).sub.2                                    reddish yellow                                          470  62    ##STR511##       C.sub.3 H.sub.6 OH                         ##STR512## orange                                          472  63    ##STR513##       C.sub.4 H.sub.8 OH                        N(C.sub.2 H.sub.4 OH).sub.2                                    reddish blue                                          595__________________________________________________________________________ 
    
     
                                           TABLE 29__________________________________________________________________________ ##STR514##                                            λmax                                      Hue of                                            (acetone)No.   D                 Z           W         Dyed Cloth                                            (nm)__________________________________________________________________________64    ##STR515##                 ##STR516## N[C.sub.3 H.sub.7 (n)].sub.2                                      deep red                                            514  65    ##STR517##       C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3                            N[C.sub.6 H.sub. 13 (sec)].sub.2                                      yellowish red                                            492  66    ##STR518##       C.sub.3 H.sub.7 (i)                             ##STR519##                                      red-brown                                            510  67    ##STR520##       CH.sub.3    N(C.sub.2 H.sub.4 CN).sub.2                                      orange                                            471  68    ##STR521##       C.sub.2 H.sub.4 OH                            N(C.sub.3 H.sub.6 CN).sub.2                                      red   496__________________________________________________________________________ 
    
     While the invention has been described in detail and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that various changes and modifications can be made therein without departing from the spirit and scope thereof.

Technology Classification (CPC): 3