Patent Publication Number: US-4150943-A

Title: Uniformly dyed water-swellable cellulosic fibers

Description:
This application is a continuation-in-part of our copending application Ser. No. 728,527 filed Oct. 1, 1976. 
    
    
     The invention relates to uniformly dyed water-swellable cellulosic fibers which are fast to washing, dry-cleaning, sublimation and light and have been produced by contacting water-swellable cellulose fibers sequently or concomitantly with water, ethylene glycol or a derivative thereof and, while the fibers are still swollen, an essentially water-insoluble dye of the formula ##STR2## IN WHICH D is the radical of a diazo component; 
     R is hydrogen, C 1  to C 7  alkyl, phenyl or phenyl bearing methyl as a substituent; 
     X is cyano, carbamoyl or substituted carbamoyl; 
     R 1  is hydrogen or an aliphatic, cycloaliphatic, araliphatic or aromatic radical; 
     R 2  is hydrogen or an aliphatic, cycloaliphatic or araliphatic radical; 
     R 3  and R 4  independently of one another have the same meanings as R 1  and R 2  ; and 
     R 1  --n--r 2  and R 3  --N--R 4  independently of one another are saturated heterocyclic radicals. 
     The radical D may be derived particularly from an amine of the benzene, naphthalene, benzothiazole, benzoisothiazole, thiazole, thiadiazole, indazole, pyrazole, thiophene, azobenzene, phthalimide, naphthalimide or anthraquinone series. 
     Examples of substituents of the radical of the diazo component D are: in the benzene series: fluoro, chloro, bromo, nitro, cyano, trifluoromethyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl, carboxylic esters such as C 1  to C 8  alkoxycarbonyl, phenoxycarbonyl, phenoxyethoxycarbonyl or β-C 1  to β-C 4  alkoxyethoxycarbonyl, optionally N-monosubstituted or N,N-disubstituted carbamoyl or sulfamoyl, methyl, ethyl, butyl, octyl, hexyl, methoxy or ethoxy and also carboxy. N-substituents of carbamoyl or sulfamoyl are for example methyl, ethyl, phenyl, benzyl, phenylethyl, cyclohexyl, norbornyl, propyl, butyl, β-hydroxyethyl, γ-hydroxypropyl, β-methoxyethyl, γ-methoxypropyl, γ-ethoxypropyl and also pyrrolidide, piperidide and morpholide. 
     In the azobenzene series: fluoro, chloro, bromo, nitro, cyano, trifluoromethyl, methyl, ethyl, carboxy, methoxy and ethoxy, the carboxylic esters, carbamoyl and sulfamoyl radicals referred to under the benzene series, and hydroxy. 
     In the heterocyclic series: chloro, bromo, nitro, cyano, methyl, ethyl, phenyl, methoxy, ethoxy, methylmercapto, β-carbomethoxyethylmercapto, β-carboethoxyethylmercapto, carbomethoxy, carboethoxy, acetyl, methylsulfonyl and ethylsulfonyl. 
     In the anthraquinone series: chloro, bromo, amino, acetyl, methyl, ethyl, phenylamino, tolylamino, hydroxy, methoxy, ethoxy, cyano and carboxy. 
     In the benzene and naphthalene series diazo components are preferred which have at least one substituent which decreases the basicity such as methylsulfonyl, phenylsulfonyl, ethylsulfonyl, carboxylic ester, optionally N-subtituted carbamoyl, chloro, bromo, trifluoromethyl and particularly cyano. 
     Radicals R other than hydrogen are for example ethyl, n-propyl, isopropyl, butyl, pentyl, α-ethylpentyl, phenyl or methylphenyl and preferably methyl. 
     Examples of R 1 , other than hydrogen, are the following substituents: alkyl of one to eight carbon atoms, alkyl of two to eight carbon atoms, alkyl of two to eight carbon atoms bearing hydroxy, cyano, alkoxy or one to eight carbon atoms, phenoxy, phenoxyethoxy or benzyloxy as a substituent, cyclohexyl, norbornyl, benzyl, phenylethyl, phenylhydroxyethyl, phenylpropyl, phenylbutyl, phenyl, phenyl bearing chloro, methyl, trifluoromethyl, pyrrolidonyl, methoxy or ethoxy as a substituent, 
     C 5  to C 12  polyalkoxyalkyl, 
     C 4  to C 9  hydroxypolyalkoxyalkyl, 
     C 1  to C 8  alkanoyloxy C 2  to C 6  alkyl, 
     C 7  to C 11  aroyloxy C 2  to C 6  alkyl, 
     C 1  to C 8  alkylaminocarbonyloxy C 2  to C 6  alkyl, 
     C 6  to C 10  arylaminocarbonyloxy C 2  to C 6  alkyl, 
     C 1  to C 8  alkoxycarbonyl C 2  to C 7  alkyl and 
     C 1  to C 18  alkanoyl, C 8  to C 10  aralkanoyl, C 7  to C 11  aroyl, 
     C 1  to C 4  alkylsulfonyl and C 6  to C 10  arylsulfonyl. 
     In addition to those already specified, the following are specific examples of suitable radicals R 1  : 
     1: unsubstituted or substituted alkyl: 
     CH 3 , C 2  H 5 , n- and i-C 3  H 7 , n- and i-C 4  H 9 , C 6  H 13 , ##STR3## CH 2  CH 2  OH, (CH 2 ) 3  OH, ##STR4## (CH 2 ) 4  OH, (CH 2 ) 6  OH, ##STR5## (CH 2 ) 2  O(CH 2 ) 2  OH, (CH 2 ) 3  O(CH 2 ) 4  OH, (CH 2 ) 3  O(CH 2 ) 2  OH, (CH 2 ) 2  CN, (CH 2 ) 5  CN, (CH 2 ) 6  CN, (CH 2 ) 7  CN, (CH 2 ) 2  O(CH 2 ) 2  CN, (CH 2 ) 3  O(CH 2 ) 2  CN, (CH 2 ) 2  O(CH 2 ) 2  O(CH 2 ) 2  CN, (CH 2 ) 3  OC 2  H 4  OCH 3 , (CH 2 ) 3  OC 2  H 4  OC 2  H 5 , (CH 2 ) 3  O(CH 2 ) 6  OH, (CH 2 ) 3  OC 2  H 4  OCH(CH 3 ) 2 , (CH 2 ) 3  OC 2  H 4  OC 4  H 9 , (CH 2 ) 3  OC 2  H 4  OCH 2  C 6  H 5 , (CH 2 ) 3  OC 2  H 4  OC 2  H 4  C 6  H 5 , ##STR6## CH 2  CH 2  COOH, (CH 2 ) 5  COOH, (CH 2 ) 6  COOH, the corresponding radicals in which the groupings: ##STR7## are present two or three times; 
     CH 2  CH 2  OCH 3 , CH 2  CH 2  OC 2  H 5 , CH 2  CH 2  OC 3  H 7 , CH 2  CH 2  OC 4  H 9 , CH 2  CH 2  OC 6  H 5 , (CH 2 ) 3  OCH 3 , (CH 2 ) 3  OC 2  H 5 , (CH 2 ) 3  OC 4  H 9 , ##STR8## (CH 2 ) 3  OC 3  H 7 , (CH 2 ) 3  OC 6  H 13 , (CH 2 ) 3  OC 8  H 17 , (CH 2 ) 3  O--, (CH 2 ) 3  OCH 2  C 6  H 5 , (CH 2 ) 3  OC 2  H 4  C 6  H 5 , (CH 2 ) 3  OC 6  H 5 , ##STR9## 
     2. unsubstituted or substituted cycloalkyl and polycycloalkyl: ##STR10## 
     3. aralkyl: 
     CH 2  C 6  H 5 , C 2  H 4  C 6  H 5 , ##STR11## as well as C 6  H 4  CH 3  instead of C 6  H 5  ; 
     4. unsubstituted or substituted phenyl; 
     C 6  H 5 , C 6  H 4  CH 3 , C 6  H 3  (CH 3 ) 2 , C 6  H 4  OCH 3 , C 6  H 4  OC 2  H 5 , C 6  H 4  OCH 2  CH 2  OH or C 6  H 4  Cl; 
     5. The radicals CH 2  CH═CH 2 , CH 2  COOCH 3 , (CH 2 ) 5  COOCH 3 , (CH 2 ) 5  COOC 2  H 5 , (CH 2 ) 5  COOC 4  H 9 , ##STR12## n being 2, 3, 4 or 6. 
     6. acyloxy: (CH 2 ) 2  OCHO, (CH 2 ) 2  OCOCH 3 , (C 2  H 4  O) 2  CHO, (C 2  H 4  O) 2  COCH 3 , (CH 2 ) 2  OCOC 3  H 7 , ##STR13## (CH 2 ) 2  OCOC 6  H 5 , (CH 2 ) 2  OCOC 6  H 4  CH 3 , (CH 2 ) 2  OCOC 6  H 4  Cl, (CH 2 ) 2  OCOC 10  H 7 , (CH 2 ) 2  OCONHCH 3 , (CH 2 ) 2  OCONHC 4  H 9 , ##STR14## (CH 2 ) 2  OCONHC 6  H 5 , (CH 2 ) 2  OCONHC 6  H 4  Cl, (CH 2 ) 2  OCONHC 6  H 3  Cl 2 , and the corresponding radicals with (CH 2 ) 3  ; (CH 2 ) 4  or (CH 2 ) 6  in each case. 
     7. acyl: 
     CHO, CH 3  CO, C 2  H 5  CO, C 3  H 7  CO, ##STR15## C 2  H 5  CO, CH 3  C 6  H 4  CO, C 6  H 5  CH 2  CO, C 6  H 5  OCH 2  CO, CH 3  SO 2 , C 2  H 5  SO 2 , C 6  H 5  SO 2  and CH 3  C 6  H 4  SO 2 . 
     Examples of preferred substituents are hydrogen, CH 3 , C 2  H 5 , n- and i-C 3  H 7 , n- and i-C 4  H 9 , C 6  H 13 , CH 2  CH 2  OH, (CH 2 ) 3  OH, ##STR16## (CH 2 ) 4  OH, (CH 2 ) 6  OH, ##STR17## (CH 2 ) 2  O(CH 2 ) 2  OH, (CH 2 ) 3  O(CH 2 ) 2  OH, (CH 2 ) 3  O(CH 2 ) 4  OH, (CH 2 ) 3  O(CH 2 ) 6  OH, ##STR18## CH 2  CH 2  OCH 3 , CH 2  CH 2  OC 2  H 5 , CH 2  CH 2  OC 4  H 9 , (CH 2 ) 3  OCH 3 , (CH 2 ) 3  OC 2  H 5 , (CH 2 ) 3  OC 3  H 7 , (CH 2 ) 3  OC 4  H 9 , ##STR19## C 6  H 5 , C 6  H 4  CH 3 , C 6  H 4  OCH 3 , C 6  H 4  OC 2  H 4  OH and (CH 2 ) 5  COOH. Examples of radicals R 1  --N--R 2  and R 3  --N--R 4  are: pyrrolidino, piperidino, morpholino, piperazino and hexamethyleneimino. 
     Dyes of the formula (I) may be prepared by reacting a diazo compound of an amine of the formula (II): 
     
         d--nh.sub.2                                                (ii) 
    
     with a coupling component of the formula (III): ##STR20## in which D, R, X, and R 1  to R 4  have the above meanings. 
     The amines are diazotized by the usual methods. Coupling is also carried out as usual in an aqueous medium, with or without the addition of a solvent, at a strongly acid to weakly acid pH. 
     The uniformly dyed fibers of the invention are preferentially obtained with dye formulations which contain, in addition to conventional dispersing agents, water retention agents and water, a dye of the formula (I) in which: 
     D is phenyl substituted by cyano, trifluoromethyl, methyl, fluoro, chloro, bromo, C 1  to C 4  alkylsulfonyl, phenylsulfonyl, ##STR21##  anthraquinonyl; anthraquinonyl substituted by methyl, chloro, bromo or carboxyl; or benzoisothiazolyl substituted by nitro, chloro or bromo; 
     R is hydrogen, C 1  to C 3  alkyl or phenyl; 
     X is cyano, carbamoyl or ##STR22## R 1  and R 3  independently of one another are hydrogen; C 1  to C 8  alkyl; C 2  to C 8  alkyl substituted by hydroxy, C 1  to C 8  alkoxy, phenoxy, tolyloxy, cyclohexyloxy, benzyloxy, β-phenylethoxy, carboxyl, carboxylic ester with a total of 2 to 9 carbon atoms, carboxylic acyloxy with a total of 1 to 11 carbon atoms, C 1  to C 8  alkylaminocarbonyloxy, benzoylaminocarbonyloxy, tolylaminocarbonyloxy, chlorophenylaminocarbonyloxy, dichlorophenylaminocarbonyloxy or pyrrolidonyl; cyclohexyl; norbornyl; phenyl-C 1  to C 4  -alkyl; tolyl-C 1  to C 4  -alkyl; β-phenyl-β-hydroxy-ethyl; phenyl; phenyl substituted by fluoro, chloro, bromo, methyl, trifluoromethyl, ethyl, methoxy, ethoxy or pyrrolidonyl; CH 2  CH 2  OCH 2  CH 2  OH; or (CH 2 ) 3  (OC 2  H 4 ) n  OB; 
     n is zero, 1 or 2; 
     B is hydrogen, C 1  to C 4  alkyl, cyclohexyl, benzyl, phenylethyl, phenyl or tolyl; 
     R 2  and R 4  independently of one another are hydrogen or C 1  to C 4  alkyl; 
     R 1  and R 2  together with the nitrogen are pyrrolidino, piperidino, morpholino or hexamethyleneimino; 
     T 1  is hydrogen, chloro, bromo or methyl; 
     T 2  is hydrogen or methyl; 
     T 3  is hydrogen, ##STR23##  or COOB 1  ; B 1  is hydrogen, C 1  to C 8  alkyl, phenyl-C 1  to C 4  -alkyl or (OC 2  H 4 ) n  OB; 
     Y is --SO 2  -- or --CO--; 
     T 4  is hydrogen or chloro; and 
     T 5  is hydrogen, methyl or ethyl. 
     Dye formulations which contain a dye or dye mixture of the formula (Ia): ##STR24## in which D 1  is a diazo component devoid of nitro groups of the benzene, phthalimide, naphthalimide, anthraquinone or azobenzene series or a nitrobenzoisothiazolyl radical; 
     A is hydrogen or C 1  to C 3  alkyl; and 
     X 1  is cyano or carbamoyl; and 
     R 1  and R 3  have the meanings given above, 
     are particularly important industrially. 
     The substituents are conveniently chosen so that the molecule contains either in the diazo component or in the coupling component at least one aryl radical and preferably a phenyl radical. 
     We have special preference for A to be methyl and X 1  to be cyano and also for the combination A═H and X 1  =CONH 2 . 
     Dyes are moreover preferred in which at least one of the radicals R 1  and R 3  contains an oxygen-containing amine radical, preferably the radical of one of the amines: phenoxyethoxypropylamine, phenoxyethoxyethoxypropylamine, benzyloxypropylamine, phenylethoxypropylamine, butoxyethoxypropylamine, benzoyloxyethylamine, benzoyloxypropylamine, benzoyloxyethoxyethylamine, H 2  N(CH 2 ) 3  O(CH 2 ) 4  OCOC 6  H 5 , H 2  N(CH 2 ) 2  OCONHC 6  H 5 , H 2  N(CH 2 ) 3  OCONHC 6  H 5  and H 2  N(CH 2 )OCONHC 6  H 4  Cl and the combination of one of these radicals with phenylamino or amino. The radical D 1  may be derived for example specifically from the following amines: o-cyanoaniline, m-cyanoaniline, p-cyanoaniline, 2,4-dicyanoaniline, 2,4,6-tribromoaniline, 2,4-dichloroaniline, 2-cyano-4,6-dibromoaniline, 2,4-dicyano-6-bromoaniline, 4-cyano-2-chloroaniline, 1-amino-2-trifluoromethyl-4-chlorobenzene, 2-chloro-5-aminobenzonitrile, 2-amino-5-chlorobenzonitrile, 1-aminobenzene-4-methylsulfone, 1-amino-2,6-dibromobenzene-4-methylsulfone, 1-amino-2-chloro-4-methylsulfone, 1-amino-2,6-dichlorobenzene-4-methylsulfone, propyl 3,5-dichloroanthranilate, β-methoxyethyl 3,5-dibromoanthranilate, 4-aminoacetophenone, 4-aminobenzophenone, 2-aminobenzophenone, 2-aminodiphenylsulfone, 4-aminodiphenylsulfone, 3-aminophthal-β-hydroxyethylimide, 4-aminophthalic phenylimide or p-tolylimide, 3-amino-6-chlorophthalimide and its N-substitution products, 3-amino-4-cyano-5-methylphthalimide and 3-amino-4-cyano-5-ethylphthalimide and their N-substitution products, 1-amino-2-chloroanthraquinone, 1-amino-2-bromoanthraquinone, 1-amino-2,4-dibromoanthraquinone, 1-amino-2-acetyl-4-chloroanthraquinone, 1-aminoanthraquinone-6-carboxylic acid, its ethyl ester, the ethyl ester of 1-aminoanthraquinone-6-carboxylic acid, 1-amino-4-methoxyanthraquinone, 1-amino-4-hydroxyanthraquinone, 1-amino-2-chloro-4-p-toluidinoanthraquinone, 2-amino-1-chloroanthraquinone, 2-amino-3-chloroanthraquinone, 2 -amino-3-bromoanthraquinone, 2-amino-1,3-dibromoanthraquinone, 2-amino-1-cyano-3-bromoanthraquinone,1-aminobenzanthrone, 6-aminobenzanthrone, 7-aminobenzanthrone, 1-aminoanthraquinone, 2-aminoanthraquinone, 1-amino-4-chloroanthraquinone, 2,4-dicyano-3,5-dimethylaniline, the imide, methylimide, n-butylimide, 2-hydroxyethylimide, 3&#39;-methoxypropylimide or phenylimide of 4-aminonaphthalic acid, 5-nitro-3-aminobenzoisothiazole-(2,1) or 5-nitro-7-bromo-3-aminobenzoisothiazole-(2,1). 
     Examples of suitable diazo components of the aminoazobenzene series are: 4-aminoazobenzene, 3-chloro-4-aminoazobenzene, 3-bromo-4-aminoazobenzene, 2&#39;,3-dimethyl-4-aminoazobenzene, 3&#39;,2-dimethyl-4-aminoazobenzene, 2,5-dimethyl-4-aminoazobenzene, 2-methyl-5-methoxy-4-aminoazobenzene, 2-methyl-4&#39;,5-dimethoxy-4-aminoazobenzene, 4&#39;-chloro-2-methyl-5-methoxy-4-aminoazobenzene, 4&#39;-chloro-2-methyl-4-aminoazobenzene, 2,5-dimethoxy-4-aminoazobenzene, 4&#39;-chloro-2,5-dimethoxy-4-aminoazobenzene, 4&#39;-chloro-2,5-dimethyl-4-aminoazobenzene, 4&#39;-methoxy-2,5-dimethyl-5-aminoazobenzene, 3,5-dibromo-4-aminoazobenzene, 2,3&#39;-dichloro-4-aminoazobenzene, 3-methoxy-4-aminoazobenzene, 2&#39;,3-dimethyl-5-bromo-4-azobenzene, 4&#39;-amino-2&#39;,5&#39;-dimethylazobenzene-4-sulfonic amide, 4&#39;-amino-2&#39;,5&#39;-dimethylazobenzene-4-sulfonic amide and the aminoazobenzenes of the formula: ##STR25## in which T 1  is hydrogen, chloro, bromo or methyl; 
     T 2  is hydrogen or methyl; and 
     T 3  is a radical of the formula ##STR26##  or --COOB 1  where Y is CO or SO 2  and B 1  is an alcohol radical and R 1  and R 2  have the meanings given above. 
     The dyes of the formula (I) may from their constitution be termed disperse dyes whose application for example to cotton is not as a rule possible. A process is described however in U.S. Pat. No. 3,706,525 which makes printing on cellulose and cellulosic textile material possible. Details given therein concerning process conditions are applicable to the dyes of the present invention. Other methods are specified in our copending application Ser. No. 691,496 according to which the dyes according to formula I may be applied. Printing processes are preferred. The above patent and application are incorporated herein by reference. 
     The dyes according to formula I give dyeings and prints having excellent fastness properties among which wet fastnesses (particularly fastness to washing, water, perspiration and sea water) and in some cases lightfastness may be emphasized. In the case of prints for example no staining of any white ground present occurs in washing. 
    
    
     In the following Examples, which illustrate the invention, parts and percentages are by weight unless specified otherwise. 
     EXAMPLE 1 
     Cotton cloth is printed by a rotary screen printing method with an ink consisting of 10 parts of the dye of the formula: ##STR27## 100 parts of polyethylene oxide of a molecular weight of 300 to 790 parts of a 3% alginate thickening and the print is dried at 100° C. The print is then treated for one minute at 200° C. with hot air, rinsed cold, soaped at the boil, again rinsed cold and dried. A light-fast and wash-fast yellow orange print is obtained on a white ground. 
     EXAMPLE 2 
     A cloth from a blend of polyester and cotton (ratio by weight 67:35) is printed with a paste consisting of 20 parts of the dye of the formula ##STR28## 120 parts of the reaction product from polyethylene oxide having a molecular weight of 300 with boric acid in the molar ratio 3:1 and 860 parts of a 10% alginate thickening. The print is dried at 105° C. and treated for six minutes at 180° C. with superheated steam. The print is then rinsed with cold water, soaped at 80° C., again rinsed cold and dried. 
     A red print which is fast to light and washing is obtained on a white ground. 
     EXAMPLE 3 
     A cotton cloth is printed by the roller printing method with a print paste consisting of 15 parts of the dye of the formula: ##STR29## 110 parts of polyethylene oxide of the molecular weight 350, 30 parts of the diethanolamide of oleic acid and 845 parts of a 10% alginate thickening. The print is dried at 100° C. and then fixed by a treatment with hot air for one minute at 195° C. The print is finished off as described in Example 1 and a fast orange print is obtained on a white ground. 
     EXAMPLE 4 
     Cloth of a blend of polyester and cellulose (ratio by weight 67:35) is printed on a screen printing machine with an ink consisting of 30 parts of the dye of the formula: ##STR30## 100 parts of the reaction product of polyethylene oxide of the molecular weight 300 with boric acid in the molar ratio 3:1, 30 parts of the diethanolamide of oleic acid and 840 parts of a 3% alginate thickening and the print is dried at 110° . It is then treated for five minutes at 185° C. with superheated steam and finished off as described in Example 2. A fast scarlet print on a white ground is obtained. 
     EXAMPLE 5 
     Cotton cloth is padded on a padding mangle with a solution containing 20 parts of the dye of the formula: ##STR31## 300 parts of a 3% alginate thickening, 550 parts of water and 130 parts of polyethylene oxide of the molecular weight 300. The cloth should take up 80% liquor. It is dried at 100° C. To fix the dye it is treated for five minutes with superheated steam at 190° C. The cloth is then rinsed cold, washed at 90° C. in a liquor containing 3 parts of the condensation product of a long chain alcohol with ethylene oxide to 997 parts of water. 
     A yellow dyeing is obtained. 
     Cloth of a blend of polyester and cotton in the ratio by weight 67:33 may be padded with the said solution instead of cotton cloth. A yellow dyeing is obtained in which the two phases are equal in tone. Fixation with hot air at 195° C. may also be carried out instead of the treatment with superheated steam. 
     EXAMPLE 6 
     Cotton cloth is padded on a padding mangle with a solution of 150 parts of polyethylene oxide in 850 parts of water so that the wet pickup is 80% and the padded cloth is dried at 100° C. The cloth treated in this way is printed by the rotary screen printing method with a color consisting of 30 parts of the dye of the formula: ##STR32## and 970 parts of a 10% alginate thickening. After the print has been dried at 105° C. it is treated for seven minutes at 185° C. with superheated steam and finished off by rinsing and soaping as described in Example 1. 
     A fast red print on a white ground is obtained. 
     The dyes specified in the following Examples may be converted as follows into a commercial dye formulation: 
     30 parts of dye, 
     6 parts of dispersing agent, 
     10 parts of a water retention agent, 
     1 part of a disinfectant and 
     about 53 parts of water 
     are ground in an agitator mill to a particle size of about 0.5 micron. A dispersion of the dye is thus obtained which is stable in storage. 
     EXAMPLE 7 
     20 Parts of 4-aminoazobenzene is stirred overnight with 80 parts by volume of 5 N hydrochloric acid. Then it is diluted with ice and water to a volume of 500 parts by volume at 10° C. 30 parts by volume of a 23% sodium nitrite solution is added and the whole is stirred for two hours at 15° C. The filtrate, in which excess nitrous acid has been removed in the conventional manner by adding sulfamic acid, is allowed to flow into a solution of 53 parts of 2,6-bis(phenoxyethoxypropylamino)-3-cyano-4-methylpyridine in 4000 parts by volume of dimethylformamide at 15° C. 150 parts by volume of a 50% aqueous sodium acetate solution is then added to this coupling mixture and the whole is stirred at 15° C. until coupling is completed. The dye formed is suction filtered, washed first with alcohol and then with hot water and dried at 90° C. A red powder is obtained which readily dissolves in dimethylformamide and polyethylene glycols with a yellowish red color and when printed in the form of these solutions or as an aqueous dispersion on cloth of polyester or cotton or a blend of the two types of fiber and aftertreated with hot air or superheated steam gives deep and clear scarlet hues. 
     EXAMPLE 8 
     35 parts of 3-chloro-4-aminoazobenzene is stirred overnight with 7 parts of an oxyethylated sperm oil alcohol containing about 23 ethylene oxide radicals and 120 parts by volume of 5 N hydrochloric acid. A volume of 750 parts by volume and a temperature of 10° C. are set up with ice and water and 450 parts by volume of a 23% aqueous sodium nitrite solution is introduced. After stirring for two hours at 15° C. a small amount of insoluble matter is filtered off and nitrous acid is removed in the usual way by adding an aqueous solution of sulfamic acid. 
     The diazonium salt solution thus obtained is then allowed to flow at 10° C. into 385 parts by volume of an isobutanol solution containing 0.16 mole of 2,6-bis-(phenoxyethoxypropylamino)-3-cyano-4-methylpyridine. Complete coupling is achieved after stirring for several hours at 15° to 25° C. without adding the usual acid-binding agents. The dye formed is suction filtered, washed first with 100 parts by volume of isobutanol and then with 100 parts of hot water and then dried at 100° C. 
     The product which is in the form of a red powder may as an aqueous dispersion or dissolved in a polyethylene glycol be printed on cloth of polyester, cotton or a blend of both types of fiber and aftertreated with hot air or superheated steam. Deep and clear red hues of very good light and wet fastness properties are thus obtained. 
     EXAMPLE 9 
     The procedure described in Example 8 is adopted but the coupling component used is 0.15 mole of the substance having the formula: ##STR33## dissolved in 8000 parts by volume of dimethylformamide. The red powder obtained after isolation and drying dissolves in dimethylformamide and polyethylene glycols with a yellowish red color. Deep and clear scarlet hues with very good fastness properties are obtained on cloth of polyester, cotton or blends of the two. 
     Red hues having similar tinctorial properties are obtained in an analogous manner with the same diazo components and the following coupling components: 
     
         __________________________________________________________________________
 ##STR34##                                                                
Ex.                                                                       
   R.sup.1                R.sup.2                                         
__________________________________________________________________________
10 H                                                                      
                           ##STR35##                                      
11                                                                        
    ##STR36##               &#34;                                             
12                                                                        
    ##STR37##               &#34;                                             
13                                                                        
    ##STR38##               &#34;                                             
14                                                                        
    ##STR39##               &#34;                                             
15   &#34;                                                                    
                           ##STR40##                                      
16                                                                        
    ##STR41##               &#34;                                             
17                                                                        
    ##STR42##               &#34;                                             
18                                                                        
    ##STR43##               &#34;                                             
19                                                                        
    ##STR44##                                                             
                           ##STR45##                                      
20                                                                        
    ##STR46##                                                             
                           ##STR47##                                      
21                                                                        
    ##STR48##                                                             
                           ##STR49##                                      
22 H                        &#34;                                             
__________________________________________________________________________
 
    
     example 23 
     16 parts of o-trifluoromethylaniline is dissolved in 30 parts by volume of 10 N hydrochloric acid and 200 parts of water, 200 parts of ice is added and then 30 parts by volume of a 23% aqueous solution of sodium nitrite is allowed to flow in below the surface. After stirring for half an hour at 0° to 5° C. the excess of nitrous acid is destroyed as usual by adding an aqueous solution of sulfamic acid. 
     The solution of the diazonium salt thus obtained is gradually added at 5° to 10° C. to a solution of 54 parts of bis-(phenoxyethoxypropylamino)-3-cyano-4-methylpyridine in 1000 parts by volume of dimethylformamide and then 32 parts by volume of a 50% aqueous sodium acetate solution is added. When coupling is over the yellow dye formed is suction filtered, washed first with alcohol and then with hot water and dried at 100° C. The yellow powder thus obtained dissolves in dimethylformamide or polyglycols with a pure yellow color and when printed on to cloth of cotton, polyester or blends of both and fixed gives deep and clear yellow hues with very good fastness properties. 
     The following dyes are obtained in a similar manner with the same coupling components: 
     
         ______________________________________                                    
                            Hue on cotton                                 
Ex.  Diazo Component        and polyester                                 
______________________________________                                    
24   m-trifluoromethylaniline                                             
                            yellow                                        
25   4-chloro-2-trifluoromethylaniline                                    
                            &#34;                                             
26   2-cyanoaniline         &#34;                                             
27   4-chloro-2-cyanoaniline                                              
                            &#34;                                             
28   2,4-dicyanoaniline     yellowish orange                              
29   2-chloroaniline-4-methylsulfone                                      
                            reddish yellow                                
30   2-aminodiphenylsulfone reddish yellow                                
31   3-aminophthalic hydroxyethylimide                                    
                            yellowish orange                              
______________________________________                                    
 
    
     EXAMPLE 32 
     25.3 Parts of the p-tolylimide of 3-aminophthalic acid is introduced at 15° to 25° C. into 60 parts of 96% sulfuric acid while stirring. The mixture is further stirred at the same temperature until complete solution has taken place. Then 32 parts (0.1 mole) of nitrosylsulfuric acid is allowed to flow in slowly at 0° to 5° C. and the diazotization mixture is stirred for another thirty minutes at 0° to 5° C. and then introduced into a mixture of 125 parts of ice and 25 parts of ice-water. 
     After the excess of nitrite has been destroyed with sulfamic acid the diazonium salt is stirred while 300 parts by volume of isobutanol and 110 parts by volume of a 10-molar solution of 2,6-bis(phenoxyethoxypropylamino)-3-cyano-4-methylpyridine in isobutanol are introduced. After coupling is over the dye formed is suction filtered, washed first with isobutanol and then with hot water and dried at 100° C. The reddish powder thus obtained dissolves in polyglycols with a reddish yellow color and gives deep orange hues with very good fastness properties on polyester, cotton or blends of the two after having been printed and fixed. 
     The following dyes may be obtained by similar methods with the same coupling components: 
     
         ______________________________________                                    
                              Hue on                                      
                              polyester                                   
Ex.  Diazo components         and cotton                                  
______________________________________                                    
33   1-aminoanthraquinone     brown                                       
34   1-aminoanthraquinone-6-carboxylic acid                               
                              brown                                       
35   1-amino-2-chloroanthraquinone                                        
                              brown                                       
36   1-amino-2-bromoanthraquinone                                         
                              brown                                       
37   1-amino-2,4-dichloroanthraquinone                                    
                              brown                                       
38   4-amino-3-methoxybenzanthrone                                        
                              brown                                       
39   2-aminoanthraquinone     red                                         
40   2-amino-3-chloroanthraquinone                                        
                              red                                         
41   2-amino-1-chloroanthraquinone                                        
                              red                                         
42   2-amino-2-cyano-3-bromoanthraquinone                                 
                              red                                         
43   2-amino-3-bromoanthraquinone                                         
                              red                                         
44   1-aminobenzanthrone      reddish violet                              
45   5-nitro-3-aminobenzoisothiazole-(2,3)                                
                              bluish violet                               
46   5-nitro-2-aminothiazole  reddish violet                              
______________________________________                                    
 
    
     The following dyes are obtainable according to the processes of the foregoing Examples: 
     
         __________________________________________________________________________
Ex.                                                                       
  Diazo components             Coupling components         Hue            
__________________________________________________________________________
47                                                                        
   ##STR50##                                                              
                                ##STR51##                  scarlet        
48                                                                        
   ##STR52##                   &#34;                           red            
49                                                                        
   ##STR53##                   &#34;                           ruby           
50                                                                        
   ##STR54##                   &#34;                           reddish        
                                                           violet         
51                                                                        
   ##STR55##                                                              
                                ##STR56##                  red            
52                                                                        
   ##STR57##                   &#34;                           red            
53                                                                        
   ##STR58##                   &#34;                           orange         
54                                                                        
   ##STR59##                                                              
                                ##STR60##                  reddish        
                                                           orange         
55                                                                        
   ##STR61##                   &#34;                           reddish        
                                                           orange         
56                                                                        
   ##STR62##                   &#34;                           scarlet        
57                                                                        
   ##STR63##                   &#34;                           yel- lowish    
                                                           orange         
58                                                                        
   ##STR64##                   &#34;                           red            
 ##STR65##                                                                
Ex.                                                                       
No.                                                                       
   D                  X    R.sup.1                                        
                               R.sup.2    Hue                             
__________________________________________________________________________
59                                                                        
    ##STR66##         CN   H   (CH.sub.2).sub.3 O(CH.sub.2).sub.2         
                               OC.sub.6 H.sub.5                           
                                          red                             
60 &#34;                  CN   C.sub.2 H.sub.5                                
                               &#34;          red                             
61 &#34;                  CN   C.sub.3 H.sub.7(n)                             
                               &#34;          red                             
62                                                                        
    ##STR67##         CN   C.sub.6 H.sub.5                                
                               &#34;          golden yellow                   
63 &#34;                  CONH.sub.2                                          
                           H   (CH.sub.2).sub.3 OCH.sub.3                 
                                          orange                          
64                                                                        
    ##STR68##         &#34;    H   &#34;          scarlet                         
65                                                                        
    ##STR69##         &#34;    H   &#34;          red                             
66                                                                        
    ##STR70##         CN   CH.sub.3                                       
                               &#34;          red                             
67 &#34;                  CONH.sub.2                                          
                           H   &#34;          red                             
68                                                                        
    ##STR71##         CN   CH.sub.3                                       
                               (CH.sub.2).sub.3 O(CH.sub.2).sub.2         
                               OC.sub.6 H.sub.5                           
                                          red                             
69 &#34;                  CN   H   &#34;          red                             
70 &#34;                  CN   CH.sub.3                                       
                               CH.sub.2 CH.sub.2 OCH.sub.3                
                                          red                             
71 &#34;                  CONH.sub.2                                          
                           H   &#34;          bluish                          
                                          red                             
72                                                                        
    ##STR72##         CN   CH.sub.3                                       
                               (CH.sub.2).sub.3 O(CH.sub.2).sub.2         
                               OC.sub.6 H.sub.5                           
                                          bluish red                      
 ##STR73##                                                                
Ex. No.                                                                   
     D                          Hue                                       
__________________________________________________________________________
73                                                                        
      ##STR74##                 scarlet                                   
74                                                                        
      ##STR75##                 scarlet                                   
75                                                                        
      ##STR76##                 scarlet                                   
76                                                                        
      ##STR77##                 red                                       
77                                                                        
      ##STR78##                 red                                       
78                                                                        
      ##STR79##                 red                                       
79                                                                        
      ##STR80##                 red                                       
80                                                                        
      ##STR81##                 red                                       
81                                                                        
      ##STR82##                 red                                       
82                                                                        
      ##STR83##                 orange                                    
83                                                                        
      ##STR84##                 orange                                    
 ##STR85##                                                                
Ex. No.                                                                   
     D                          Hue                                       
__________________________________________________________________________
84                                                                        
      ##STR86##                 golden yellow                             
85                                                                        
      ##STR87##                 golden yellow                             
86                                                                        
      ##STR88##                 orange                                    
87                                                                        
      ##STR89##                 orange                                    
88                                                                        
      ##STR90##                 ruby                                      
 ##STR91##                                                                
Ex. No.                                                                   
     D                          Hue                                       
__________________________________________________________________________
89                                                                        
      ##STR92##                 scarlet                                   
90                                                                        
      ##STR93##                 red                                       
91                                                                        
      ##STR94##                 red                                       
92                                                                        
      ##STR95##                 red                                       
93                                                                        
      ##STR96##                 red                                       
94                                                                        
      ##STR97##                 red                                       
95                                                                        
      ##STR98##                 red                                       
96                                                                        
      ##STR99##                 red                                       
97                                                                        
      ##STR100##                red                                       
98                                                                        
      ##STR101##                red                                       
99                                                                        
      ##STR102##                orange                                    
100                                                                       
      ##STR103##                golden yellow                             
101                                                                       
      ##STR104##                orange                                    
102                                                                       
      ##STR105##                orange                                    
 ##STR106##                                                               
Ex. No.                                                                   
     D                  R        Hue                                      
__________________________________________________________________________
103                                                                       
      ##STR107##        H        reddish orange                           
104  &#34;                  CH.sub.3 reddish                                  
                                 orange                                   
105  &#34;                  COC.sub.6 H.sub.5                                 
                                 reddish                                  
                                 orange                                   
106                                                                       
      ##STR108##        &#34;        golden yellow                            
107                                                                       
      ##STR109##        &#34;        golden yellow                            
108                                                                       
      ##STR110##        &#34;        reddish orange                           
109  &#34;                  H        reddish                                  
                                 orange                                   
110                                                                       
      ##STR111##        H        red                                      
111                                                                       
      ##STR112##        COC.sub.6 H.sub.5                                 
                                 red                                      
112  &#34;                                                                    
                         ##STR113##                                       
                                 red                                      
113  &#34;                  CH.sub.3 red                                      
114  &#34;                  C.sub.2 H.sub.5                                   
                                 red                                      
115                                                                       
      ##STR114##        &#34;        red                                      
116  &#34;                  CH.sub.3 red                                      
117  &#34;                  H        red                                      
118                                                                       
      ##STR115##        H        yellowish orange                         
119  &#34;                  CH.sub.3 yellowish                                
                                 orange                                   
120  &#34;                  C.sub.2 H.sub.5                                   
                                 yellowish                                
                                 orange                                   
121                                                                       
      ##STR116##        C.sub.2 H.sub.5                                   
                                 red                                      
122  &#34;                  CH.sub.3 red                                      
123  &#34;                  H        red                                      
 ##STR117##                                                               
Ex. No.                                                                   
     D                  Hue                                               
__________________________________________________________________________
124                                                                       
      ##STR118##        golden yellow                                     
125                                                                       
      ##STR119##        orange                                            
126                                                                       
      ##STR120##        golden yellow                                     
127                                                                       
      ##STR121##        reddish orange                                    
128                                                                       
      ##STR122##        red                                               
129                                                                       
      ##STR123##        red                                               
130                                                                       
      ##STR124##        reddish orange                                    
131                                                                       
      ##STR125##        reddish orange                                    
132                                                                       
      ##STR126##        red                                               
133                                                                       
      ##STR127##        red                                               
134                                                                       
      ##STR128##        orange                                            
135                                                                       
      ##STR129##        orange                                            
 ##STR130##                                                               
Ex. No.                                                                   
     D                  Hue                                               
__________________________________________________________________________
136                                                                       
      ##STR131##        bluish red                                        
137                                                                       
      ##STR132##        bluish red                                        
138                                                                       
      ##STR133##        Bordeaux                                          
139                                                                       
      ##STR134##        Bordeaux                                          
140                                                                       
      ##STR135##        bluish red                                        
141                                                                       
      ##STR136##        orange                                            
142                                                                       
      ##STR137##        orange                                            
 ##STR138##                                                               
Ex. No.                                                                   
     D                  Hue                                               
__________________________________________________________________________
143                                                                       
      ##STR139##        reddish orange                                    
144                                                                       
      ##STR140##        red                                               
145                                                                       
      ##STR141##        red                                               
146                                                                       
      ##STR142##        red                                               
147                                                                       
      ##STR143##        red                                               
148                                                                       
      ##STR144##        reddish orange                                    
149                                                                       
      ##STR145##        reddish orange                                    
150                                                                       
      ##STR146##        golden yellow                                     
151                                                                       
      ##STR147##        golden yellow                                     
152                                                                       
      ##STR148##        golden yellow                                     
153                                                                       
      ##STR149##        golden yellow                                     
 ##STR150##                                                               
Ex. No.                                                                   
     D                  Hue                                               
__________________________________________________________________________
154                                                                       
      ##STR151##        reddish orange                                    
155                                                                       
      ##STR152##        red                                               
156                                                                       
      ##STR153##        red                                               
157                                                                       
      ##STR154##        red                                               
158                                                                       
      ##STR155##        red                                               
159                                                                       
      ##STR156##        orange                                            
160                                                                       
      ##STR157##        orange                                            
161                                                                       
      ##STR158##        golden yellow                                     
162                                                                       
      ##STR159##        golden yellow                                     
163                                                                       
      ##STR160##        golden yellow                                     
164                                                                       
      ##STR161##        golden yellow                                     
 ##STR162##                                                               
Ex. No.                                                                   
     D                  Hue                                               
__________________________________________________________________________
165                                                                       
      ##STR163##        reddish  orange                                   
166                                                                       
      ##STR164##        red                                               
167                                                                       
      ##STR165##        red                                               
168                                                                       
      ##STR166##        red                                               
169                                                                       
      ##STR167##        red                                               
170                                                                       
      ##STR168##        reddish orange                                    
171                                                                       
      ##STR169##        reddish orange                                    
172                                                                       
      ##STR170##        golden yellow                                     
173                                                                       
      ##STR171##        golden  yellow                                    
174                                                                       
      ##STR172##        golden yellow                                     
175                                                                       
      ##STR173##        golden yellow                                     
 ##STR174##                                                               
Ex. No.                                                                   
     D                  Hue                                               
__________________________________________________________________________
176                                                                       
      ##STR175##        reddish orange                                    
177                                                                       
      ##STR176##        red                                               
178                                                                       
      ##STR177##        red                                               
179                                                                       
      ##STR178##        red                                               
180                                                                       
      ##STR179##        red                                               
181                                                                       
      ##STR180##        reddish orange                                    
182                                                                       
      ##STR181##        reddish orange                                    
183                                                                       
      ##STR182##        golden yellow                                     
184                                                                       
      ##STR183##        golden yellow                                     
185                                                                       
      ##STR184##        golden yellow                                     
186                                                                       
      ##STR185##        golden yellow                                     
 ##STR186##                                                               
Ex.                                                                       
No.                                                                       
   R.sup.1            R.sup.2      Hue                                    
__________________________________________________________________________
187                                                                       
    ##STR187##                                                            
                       ##STR188##  yellow                                 
188                                                                       
    ##STR189##        &#34;            yellow                                 
189                                                                       
   NH.sub.2           &#34;            yellow                                 
190                                                                       
    ##STR190##                                                            
                       ##STR191##  yellow                                 
191                                                                       
   &#34;                                                                      
                       ##STR192##  yellow                                 
192                                                                       
   &#34;                                                                      
                       ##STR193##  yellow                                 
 ##STR194##                                                               
__________________________________________________________________________
193                                                                       
   NH.sub.2                                                               
                       ##STR195##  yellow                                 
Coupling components   Diazo component                                     
 ##STR196##                                                               
                       ##STR197##                                         
__________________________________________________________________________
194                                                                       
    ##STR198##                                                            
                       ##STR199##  yellow                                 
 ##STR200##                                                               
                       ##STR201##                                         
__________________________________________________________________________
195                                                                       
    ##STR202##                                                            
                       ##STR203##  golden yellow                          
196                                                                       
    ##STR204##                                                            
                       ##STR205##  orange                                 
197                                                                       
   &#34;                                                                      
                       ##STR206##  orange                                 
198                                                                       
   &#34;                                                                      
                       ##STR207##  orange                                 
Coupling components   Diazo component                                     
 ##STR208##                                                               
                       ##STR209##                                         
__________________________________________________________________________
199                                                                       
    ##STR210##                                                            
                       ##STR211##  golden yellow                          
200                                                                       
    ##STR212##                                                            
                       ##STR213##  orange                                 
201                                                                       
   &#34;                                                                      
                       ##STR214##  orange                                 
Coupling components   Diazo component                                     
 ##STR215##                                                               
                       ##STR216##                                         
__________________________________________________________________________
202                                                                       
    ##STR217##                                                            
                       ##STR218##  golden yellow                          
203                                                                       
   NH.sub.2           &#34;            orange                                 
204                                                                       
    ##STR219##                                                            
                       ##STR220##  orange                                 
205                                                                       
   &#34;                                                                      
                       ##STR221##  orange                                 
206                                                                       
   &#34;                                                                      
                       ##STR222##  orange                                 
207                                                                       
   &#34;                                                                      
                       ##STR223##  golden yellow                          
208                                                                       
   &#34;                                                                      
                       ##STR224##  golden yellow                          
Coupling components   Diazo component                                     
 ##STR225##                                                               
                       ##STR226##                                         
__________________________________________________________________________
209                                                                       
    ##STR227##                                                            
                       ##STR228##  orange                                 
210                                                                       
   &#34;                                                                      
                       ##STR229##  orange                                 
211                                                                       
   &#34;                                                                      
                       ##STR230##  orange                                 
212                                                                       
   &#34;                                                                      
                       ##STR231##  orange                                 
213                                                                       
   &#34;                                                                      
                       ##STR232##  orange                                 
Coupling components   Diazo component                                     
 ##STR233##                                                               
                       ##STR234##                                         
__________________________________________________________________________
214                                                                       
    ##STR235##                                                            
                       ##STR236##  reddish  orange                        
215                                                                       
    ##STR237##                                                            
                       ##STR238##  &#34;                                      
216                                                                       
    ##STR239##                                                            
                       ##STR240##  &#34;                                      
217                                                                       
   &#34;                                                                      
                       ##STR241##  red                                    
218                                                                       
   &#34;                                                                      
                       ##STR242##  &#34;                                      
219                                                                       
   NH.sub.2                                                               
                       ##STR243##  orange                                 
Coupling Components   Diazo component                                     
 ##STR244##                                                               
__________________________________________________________________________
220                                                                       
    ##STR245##                                                            
                       ##STR246##  red                                    
221                                                                       
    ##STR247##        &#34;            &#34;                                      
222                                                                       
   &#34;                                                                      
                       ##STR248##  &#34;                                      
223                                                                       
   NH.sub.2                                                               
                       ##STR249##  &#34;                                      
224                                                                       
    ##STR250##                                                            
                       ##STR251##  &#34;                                      
225                                                                       
   &#34;                                                                      
                       ##STR252##  &#34;                                      
226                                                                       
   &#34;                                                                      
                       ##STR253##  &#34;                                      
227                                                                       
   &#34;                                                                      
                       ##STR254##  &#34;                                      
Coupling components   Diazo component                                     
 ##STR255##                                                               
__________________________________________________________________________
228                                                                       
    ##STR256##                                                            
                       ##STR257##   violetBluish                          
229                                                                       
   &#34;                                                                      
                       ##STR258##  &#34;                                      
230                                                                       
    ##STR259##        &#34;            &#34;                                      
231                                                                       
   NH.sub.2           &#34;            violet                                 
232                                                                       
    ##STR260##                                                            
                       ##STR261##   violetbluish                          
233                                                                       
   &#34;                                                                      
                       ##STR262##  blue                                   
234                                                                       
   &#34;                  N            &#34;                                      
235                                                                       
   &#34;                  N            &#34;                                      
Ex. No. 236                                                               
       ##STR263##                    red                                  
 ##STR264##                                                               
Ex.                                                                       
No.                                                                       
   R.sup.1                     R.sup.2                                    
                                  R.sup.3                                 
                                     R.sup.4    R.sup.5    Hue            
__________________________________________________________________________
237                                                                       
    ##STR265##                 CH.sub.3                                   
                                  CH.sub.3                                
                                     CH.sub.2 CH.sub.2 OCH.sub.3          
                                                CH.sub.2 CH.sub.2         
                                                OCH.sub.3  red            
238                                                                       
   &#34;                           &#34;  &#34;  CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 
                                                CH.sub.2 CH.sub.2         
                                                CH.sub.2 OCH.sub.3        
                                                           &#34;              
239                                                                       
   &#34;                           &#34;  &#34;  &#34;          C.sub.6 H.sub.5           
                                                           &#34;              
240                                                                       
    ##STR266##                 &#34;  &#34;  &#34;          &#34;          &#34;              
241                                                                       
    ##STR267##                 &#34;  &#34;  &#34;          &#34;          &#34;              
242                                                                       
   &#34;                           &#34;  &#34;  &#34;          CH.sub.2 CH.sub.2         
                                                CH.sub.2 OCH.sub.3        
                                                           &#34;              
243                                                                       
   &#34;                           H  &#34;  &#34;          &#34;          &#34;              
244                                                                       
   &#34;                           Cl H  &#34;          &#34;          &#34;              
245                                                                       
    ##STR268##                 CH.sub.3                                   
                                  CH.sub.3                                
                                     &#34;          C.sub.6 H.sub.5           
                                                           &#34;              
246                                                                       
   &#34;                           &#34;  &#34;  &#34;          (CH.sub.2).sub.3 O(CH.sub.
                                                2).sub.2 OC.sub.6         
                                                           &#34;.sub.5        
247                                                                       
    ##STR269##                 &#34;  &#34;  &#34;          &#34;          &#34;              
248                                                                       
    ##STR270##                 &#34;  &#34;  (CH.sub.2).sub.3 O(CH.sub.2 O(C.sub.6
                                      H.sub.5   &#34;          &#34;              
249                                                                       
    ##STR271##                 &#34;  &#34;  &#34;          &#34;          &#34;              
250                                                                       
    ##STR272##                 &#34;  &#34;  &#34;          &#34;          &#34;              
251                                                                       
   &#34;                           &#34;  &#34;  (CH.sub.2).sub.3 OCH.sub.3           
                                                &#34;          &#34;              
252                                                                       
   H                           Cl H  (CH.sub.2).sub.5COOH                 
                                                &#34;          &#34;              
253                                                                       
   HOOC                        CH.sub.3                                   
                                  CH.sub.3                                
                                     (CH.sub.2).sub.3 O(CH.sub.2).sub.2   
                                     OC.sub.6 H.sub.5                     
                                                &#34;          &#34;              
254                                                                       
   H                           H  H  (CH.sub.2).sub.5COOH                 
                                                &#34;          orange         
255                                                                       
   H                           CH.sub.3                                   
                                  CH.sub.3                                
                                     &#34;          &#34;          &#34;              
256                                                                       
   H                           Cl H  (CH.sub.2).sub.3 O(CH.sub.2).sub.2   
                                     OC.sub.6 H.sub.5                     
                                                COCH.sub.3 scarlet        
257                                                                       
   &#34;                           &#34;  &#34;  &#34;          SO.sub.2 CH.sub.3         
                                                           &#34;              
Coupling component                                                        
 ##STR273##                                                               
   Diazo components    Hue                                                
__________________________________________________________________________
258                                                                       
    ##STR274##         yellow                                             
259                                                                       
    ##STR275##         orange                                             
260                                                                       
    ##STR276##         &#34;                                                  
261                                                                       
    ##STR277##         scarlet                                            
262                                                                       
    ##STR278##         &#34;                                                  
263                                                                       
    ##STR279##         &#34;                                                  
264                                                                       
    ##STR280##         bluish red                                         
265                                                                       
    ##STR281##         &#34;                                                  
266                                                                       
    ##STR282##         reddish violet                                     
267                                                                       
    ##STR283##         &#34;                                                  
268                                                                       
    ##STR284##         ruby                                               
269                                                                       
   trichloroaniline    yellow                                             
270                                                                       
   tribromoaniline     yellow                                             
Coupling component                                                        
 ##STR285##                                                               
Ex.                                                                       
   Diazo components                                                       
                 R  X   R.sup.3    Hue                                    
__________________________________________________________________________
271                                                                       
   1-aminoanthraquinone                                                   
                 CH.sub.3                                                 
                    CN  H          brown                                  
272                                                                       
   &#34;             H  CN  H          brown                                  
273                                                                       
   &#34;             H  CONH.sub.2                                            
                        H          reddish brown                          
274                                                                       
   &#34;             CH.sub.3                                                 
                    CN  C.sub.6 H.sub.5                                   
                                   brown                                  
275                                                                       
   &#34;             H  CN  C.sub.6 H.sub.5                                   
                                   brown                                  
276                                                                       
   &#34;             H  CONH.sub.2                                            
                        C.sub.6 H.sub.5                                   
                                   reddish brown                          
277                                                                       
   &#34;             CH.sub.3                                                 
                    CN  C.sub.6 H.sub.4 CH.sub.3 (p)                      
                                   brown                                  
278                                                                       
   1-amino-2-chloroanthra-                                                
                 CH.sub.3                                                 
                    CN  H          brown                                  
   quinone                                                                
279                                                                       
   &#34;             CH.sub.3                                                 
                    CN  C.sub.6 H.sub.5                                   
                                   brown                                  
280                                                                       
   &#34;             CH.sub.3                                                 
                    CN  C.sub.6 H.sub.4 CH.sub.3 (p                       
                                   brown                                  
281                                                                       
   &#34;             H  CN  C.sub.6 H.sub.5                                   
                                   brown                                  
282                                                                       
   &#34;             H  CONH.sub.2                                            
                        C.sub.6 H.sub.5                                   
                                   reddish brown                          
283                                                                       
   1-amino-2-methylanthraquin-                                            
                 CH.sub.3                                                 
                    CN  H          brown                                  
   one                                                                    
284                                                                       
   &#34;             CH.sub.3                                                 
                    CN  C.sub.6 H.sub.5                                   
                                   brown                                  
285                                                                       
   3-amino-5-nitro-benzoiso-                                              
                 H  CN  H          violet                                 
   thiazole-(2,1)                                                         
286                                                                       
   &#34;             H  CONH.sub.2                                            
                        H          navy blue                              
287                                                                       
   &#34;             H  CONH.sub.2                                            
                        C.sub.6 H.sub.5                                   
                                   blue                                   
288                                                                       
   3-amino-5-nitro-7-bromo-                                               
                 H  CONH.sub.2                                            
                        C.sub.6 H.sub.5                                   
                                   blue                                   
   benzoisothiazole-(2,1)                                                 
289                                                                       
   &#34;             H  CONH.sub.2                                            
                        H          navy blue                              
290                                                                       
   &#34;             H  CN  H          bluish violet                          
291                                                                       
    ##STR286##   CH.sub.3                                                 
                    CN  H          orange                                 
292                                                                       
   &#34;             CH.sub.3                                                 
                    CN  C.sub.6 H.sub.5                                   
                                   orange                                 
293                                                                       
   &#34;             H  CN  H          orange                                 
294                                                                       
   &#34;             H  CONH.sub.2                                            
                        H          scarlet                                
295                                                                       
   &#34;             H  CONH.sub.2                                            
                        C.sub.6 H.sub.5                                   
                                   scarlet                                
296                                                                       
    ##STR287##   CH.sub.3                                                 
                    CN  C.sub.6 H.sub.5                                   
                                   orange                                 
297                                                                       
   &#34;             H  CN  C.sub.6 H.sub.5                                   
                                   orange                                 
298                                                                       
   &#34;             H  CONH.sub.2                                            
                        C.sub.6 H.sub.5                                   
                                   scarlet                                
299                                                                       
   &#34;             H  CONH.sub.2                                            
                        H          orange                                 
300                                                                       
    ##STR288##   H  CN  H          red                                    
301                                                                       
   &#34;             H  CN  C.sub.6 H.sub.5                                   
                                   red                                    
302                                                                       
   &#34;             H  CONH.sub.2                                            
                        C.sub.6 H.sub.5                                   
                                   ruby                                   
303                                                                       
   &#34;             H  CONH.sub.2                                            
                        H          ruby                                   
304                                                                       
   &#34;             H  CN  (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OC.sub.6        
                        H.sub.5    red                                    
305                                                                       
    ##STR289##   H  CONH.sub.2                                            
                        H          ruby                                   
306                                                                       
   &#34;             H  CN  H          red                                    
307                                                                       
   &#34;             H  CN  C.sub.6 H.sub.5                                   
                                   red                                    
308                                                                       
   &#34;             CH.sub.3                                                 
                    CN  (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OC.sub.6        
                                   red                                    
309                                                                       
    ##STR290##   CH.sub.3                                                 
                    CN  H          orange                                 
310                                                                       
   &#34;             H  CN  H          orange                                 
311                                                                       
   &#34;             H  CONH.sub.2                                            
                        H          scarlet                                
Coupling components                                                       
 ##STR291##                                                               
Ex.                                                                       
   Diazo components                                                       
                 R.sup.3                                                  
                        Z          Hue                                    
__________________________________________________________________________
312                                                                       
    ##STR292##   H      (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OC.sub.6        
                        H.sub.5    orange                                 
313                                                                       
   &#34;             C.sub.6 H.sub.5                                          
                        &#34;          orange                                 
314                                                                       
    ##STR293##   H      &#34;          orange                                 
315                                                                       
    ##STR294##   H      &#34;          orange                                 
316                                                                       
    ##STR295##   H      &#34;          scarlet                                
317                                                                       
    ##STR296##   H      &#34;          scarlet                                
318                                                                       
   3-aminophthalic p-tolyl-                                               
                 H      &#34;          red                                    
   imide                                                                  
319                                                                       
   1-aminoanthraquinine                                                   
                 H      &#34;          reddish brown                          
320                                                                       
   aminoazobenzene                                                        
                 H      &#34;          ruby                                   
321                                                                       
   chloroaminoazobenzene                                                  
                 H      &#34;          reddish violet                         
322                                                                       
   bromoaminoazobenzene                                                   
                 H      &#34;          reddish violet                         
323                                                                       
   3-amino-5-nitrobenziso-                                                
                 H      &#34;          navy blue                              
   thiazole-(2,1)                                                         
324                                                                       
   &#34;             C.sub.6 H.sub.5                                          
                        &#34;          navy blue                              
325                                                                       
   &#34;             C.sub.6 H.sub.4 CH.sub.3 (p)                             
                        &#34;          navy blue                              
326                                                                       
   3-amino-5-nitro-7-bromo-                                               
                 H      &#34;          navy blue                              
   benzoisothiazole-(2,1)                                                 
327                                                                       
   &#34;             C.sub.6 H.sub.5                                          
                        &#34;          navy blue                              
328                                                                       
   4-aminoazobenzene                                                      
                 H      H          orange                                 
329                                                                       
   4-amino-3-chloroazobenzene                                             
                 H      H          scarlet                                
The following are also suitable as dyes:                                  
Example                                        Hue                        
__________________________________________________________________________
330                                                                       
      ##STR297##                               orange                     
331                                                                       
      ##STR298##                               yellow                     
332                                                                       
      ##STR299##                               brown                      
333                                                                       
      ##STR300##                               red                        
      ##STR301##                                                          
Example                                                                   
     R                                         Hue                        
__________________________________________________________________________
334  C.sub.6 H.sub.5                           red                        
335  C.sub.6 H.sub.4 CH.sub.3 (o)              red                        
336  C.sub.6 H.sub.4 CH.sub.3 (p)              red                        
337                                                                       
      ##STR302##                               red                        
 ##STR303##                                                               
Example                                                                   
       D                      R.sup.1       R.sup.3      Hue              
__________________________________________________________________________
338                                                                       
        ##STR304##            (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.6 
                              H.sub.5       (CH.sub.2).sub.3 (CH.sub.2).su
                                            b.2 OC.sub.6 H.sub.5          
                                                         orange           
339                                                                       
        ##STR305##            &#34;             &#34;            orange           
340                                                                       
        ##STR306##            &#34;                                           
                                             ##STR307##  orange           
341    &#34;                      &#34;                                           
                                             ##STR308##  orange           
342    &#34;                      &#34;             (CH.sub.2).sub.2C.sub.6       
                                            H.sub.5      orange           
343    &#34;                                                                  
                               ##STR309##   (CH.sub.2).sub.3 O(CH.sub.2).s
                                            ub.2 OC.sub.6 H.sub.5         
                                                         orange           
344                                                                       
        ##STR310##            (CH.sub.2).sub.2 OCH.sub.3                  
                                            (CH.sub.2).sub.2 OCH.sub.3    
                                                         orange           
345    &#34;                      (CH.sub.2).sub.3 OCH.sub.3                  
                                            (CH.sub.2).sub.               
                                                         orangesub.3      
346    &#34;                      (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.6 
                              H.sub.5       (CH.sub.2).sub.3 O(CH.sub.2).s
                                            ub.2 OC.sub.6 H.sub.5         
                                                         orange           
347                                                                       
        ##STR311##            (CH.sub.2).sub.2 OCH.sub.3                  
                                            (CH.sub.2).sub.2 OCH.sub.3    
                                                         orange           
348    &#34;                      (CH.sub.2).sub.3 OCH.sub.3                  
                                            (CH.sub.2).sub.3 OCH.sub.3    
                                                         orange           
349    &#34;                      (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.6 
                              H.sub.5       (CH.sub.2).sub.3 O(CH.sub.2).s
                                            ub.2 OC.sub.6 H.sub.5         
                                                         orange           
Example                                                                   
      D                      R.sup.1       R.sup.2       Hue              
__________________________________________________________________________
350                                                                       
       ##STR312##            (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.6  
                             H.sub.5       (CH.sub.2).sub.3 O(CH.sub.2).su
                                           b.2 OC.sub.6 H.sub.5           
                                                         orange           
351                                                                       
       ##STR313##            &#34;             &#34;             orange           
352                                                                       
       ##STR314##            &#34;             &#34;             orange           
353                                                                       
       ##STR315##            &#34;             &#34;             orange           
354                                                                       
       ##STR316##            &#34;             &#34;             orange           
355                                                                       
       ##STR317##            &#34;             &#34;             orange           
356                                                                       
       ##STR318##            &#34;             &#34;             orange           
357                                                                       
       ##STR319##            &#34;             &#34;             orange           
358                                                                       
       ##STR320##            &#34;             &#34;             orange           
359   &#34;                      NH.sub.2      &#34;             orange           
360   &#34;                      (CH.sub.2).sub.2 OCH.sub.3                   
                                           (CH.sub.2).sub.2 OCH.sub.3     
                                                         orange           
361   &#34;                      (CH.sub.2).sub.3 OCH.sub.3                   
                                           (CH.sub.2).sub.3 OCH.sub.3     
                                                         orange           
Example                                                                   
     D                    R.sup.1    R.sup.3    Hue                       
__________________________________________________________________________
362                                                                       
      ##STR321##          (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.4     
                          H.sub.9    (CH.sub.2).sub.3 O(CH.sub.2).sub.2   
                                     OC.sub.4 H.sub.9                     
                                                red                       
363                                                                       
      ##STR322##          &#34;          &#34;          brown                     
364                                                                       
      ##STR323##          &#34;          &#34;          orange                    
365                                                                       
      ##STR324##          &#34;          &#34;          orange                    
366                                                                       
      ##STR325##          &#34;          &#34;          orange                    
367                                                                       
      ##STR326##          &#34;          &#34;          orange                    
 ##STR327##                                                               
Exam-                                                                     
ple T.sup.3         T.sup.4                                               
                      T.sup.5       R.sup.3     R.sup.1     Hue           
__________________________________________________________________________
368 SO.sub.2 NH(CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.6 H.sub.5        
                    H H             (CH.sub.2).sub.2 OCH.sub.3            
                                                (CH.sub.2).sub.2 OCH.sub.3
                                                            red           
369 &#34;                 &#34;             (CH.sub.2).sub.3 OCH.sub.3            
                                                (CH.sub.2).sub.3 OCH.sub.3
                                                            red           
370 &#34;                 &#34;             (CH.sub.2).sub.3 O(CH.sub. 2).sub.2   
                                    OC.sub.6 H.sub.5                      
                                                (CH.sub.2).sub.3 O(CH.sub.
                                                2).sub.2 OC.sub.6         
                                                            redub.5       
371 &#34;                 &#34;             (CH.sub.2).sub.3 O(CH.sub.2).sub.2    
                                    OC.sub.6 H.sub.5                      
                                                (CH.sub.2).sub.3 O(CH.sub.
                                                2).sub.2 OC.sub.6         
                                                            redub.5       
372 &#34;               Cl                                                    
                      &#34;             &#34;           &#34;           red           
373 &#34;               Cl                                                    
                      &#34;             (CH.sub.2).sub.2 OCH.sub.3            
                                                (CH.sub.2).sub.2 OCH.sub.3
                                                            red           
374 &#34;               Cl                                                    
                      &#34;             (CH.sub.2).sub.3 OCH.sub.3            
                                                (CH.sub.2).sub.3 OCH.sub.3
                                                            red           
375 CONH(CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.6 H.sub.5               
                    H &#34;             &#34;           &#34;           red           
376 &#34;               H &#34;             (CH.sub.2).sub.2 OCH.sub.3            
                                                (CH.sub.2).sub.2 OCH.sub.3
                                                            red           
377 &#34;               H &#34;             (CH.sub.2).sub.3 O(CH.sub.2).sub.2    
                                    OC.sub.6 H.sub.5                      
                                                (CH.sub.2).sub.3 O(CH.sub.
                                                2).sub.2 OC.sub.6         
                                                            redub.5       
378 Cl              Cl                                                    
                      SO.sub.2 NH(CH.sub.2).sub.3 OC.sub.2 H.sub.4        
                      OC.sub.6 H.sub.5                      red           
 ##STR328##                                                               
Example                                                                   
     R.sup.1            Hue                                               
__________________________________________________________________________
379                                                                       
      ##STR329##        bluish violet                                     
380                                                                       
      ##STR330##        blue                                              
381                                                                       
      ##STR331##        blue                                              
382  (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.4 H.sub.9                  
                        bluish violet                                     
383                                                                       
      ##STR332##        blue                                              
 ##STR333##                                                               
Example                                                                   
     D               R  X    Hue                                          
__________________________________________________________________________
384                                                                       
      ##STR334##     CH.sub.3                                             
                        CN   scarlet                                      
385  &#34;               H  CN   scarlet                                      
386  &#34;               H  CONH.sub.2                                        
                             red                                          
387                                                                       
      ##STR335##     CH.sub.3                                             
                        CN   red                                          
388  &#34;               H  CN   red                                          
389  &#34;               H  CONH.sub.2                                        
                             ruby                                         
390                                                                       
      ##STR336##     CH.sub.3                                             
                        CN   yellow                                       
391  &#34;               H  CONH.sub.2                                        
                             orange                                       
392                                                                       
      ##STR337##     CH.sub.3                                             
                        CN   yellowish orange                             
393  &#34;               H  CONH.sub.2                                        
                             reddish orange                               
394                                                                       
      ##STR338##     CH.sub.3                                             
                        CN   orange                                       
395  &#34;               H  CONH.sub.2                                        
                             scarlet                                      
 ##STR339##                                                               
No.                                                                       
   T.sup.4                                                                
      T.sup.3      T.sup.1                                                
                      T.sup.2                                             
                         R.sup.3                                          
                                R.sup.1                                   
                                       shade                              
__________________________________________________________________________
396                                                                       
   H  H            H  H  C.sub.4 H.sub.9 (n)                              
                                C.sub.4 H.sub.9 (n)                       
                                       orange                             
397                                                                       
   4-Cl                                                                   
      H            CH.sub.3                                               
                      H  C.sub.3 H.sub.7 (n)                              
                                C.sub.3 H.sub.7 (n)                       
                                       red                                
398                                                                       
   4-Cl                                                                   
      H            CH.sub.3                                               
                      CH.sub.3                                            
                         C.sub.2 H.sub.5                                  
                                C.sub.2 H.sub.5                           
                                       red                                
399                                                                       
   4-Cl                                                                   
      H            CH.sub.3                                               
                      H  &#34;      &#34;      red                                
400                                                                       
   2-Cl                                                                   
      H            CH.sub.3                                               
                      CH.sub.3                                            
                         &#34;      &#34;      red                                
401                                                                       
   4-Cl                                                                   
      H            CH.sub.3                                               
                      H  C.sub.4 H.sub.9 (n)                              
                                C.sub.4 H.sub.9 (n)                       
                                       red                                
402                                                                       
   H  H            Br H  &#34;      &#34;      red                                
403                                                                       
   3-Cl                                                                   
      H            CH.sub.3                                               
                      CH.sub.3                                            
                         (CH.sub.2 ).sub.3 OCH.sub.3                      
                                (CH.sub.2).sub.3 OCH.sub.3                
                                       red                                
404                                                                       
   3-Cl                                                                   
      H            CH.sub.3                                               
                      CH.sub.3                                            
                         (CH.sub.2).sub.2 OCH.sub.3                       
                                (CH.sub.2).sub.2 OCH.sub.3                
                                       red                                
405                                                                       
   4-Cl                                                                   
      H            CH.sub.3                                               
                      CH.sub.3                                            
                         &#34;      &#34;      red                                
406                                                                       
   4-Cl                                                                   
      H            CH.sub.3                                               
                      CH.sub.3                                            
                         (CH.sub.2).sub.3 OCH.sub.3                       
                                (CH.sub.2).sub.3 OCH.sub.3                
                                       red                                
407                                                                       
   4-Cl                                                                   
      H            CH.sub.3                                               
                      H  &#34;      &#34;      red                                
408                                                                       
   4-Cl                                                                   
      H            CH.sub.3                                               
                      H  (CH.sub.2).sub.2 OCH.sub.3                       
                                (CH.sub.2).sub.2 OCH.sub.3                
                                       red                                
409                                                                       
   H  H            Cl H  C.sub.4 H.sub.9 (n)                              
                                C.sub.4 H.sub.9 (n)                       
                                       red                                
410                                                                       
   2-Cl                                                                   
      H            CH.sub.3                                               
                      H  C.sub.2 H.sub.5                                  
                                C.sub.2 H.sub.5                           
                                       red                                
411                                                                       
   2-Cl                                                                   
      H            CH.sub.3                                               
                      H  (CH.sub.2).sub.2 OCH.sub.3                       
                                (CH.sub.2).sub.2 OCH.sub.3                
                                       red                                
412                                                                       
   2-Cl                                                                   
      H            CH.sub.3                                               
                      H  (CH.sub.2).sub.3 OCH.sub.3                       
                                (CH.sub.2).sub.3 OCH.sub.3                
                                       red                                
413                                                                       
   3-Cl                                                                   
      H            CH.sub.3                                               
                      H  (CH.sub.2).sub.3 OCH.sub.3                       
                                (CH.sub.2).sub.3 OCH.sub.3                
                                       red                                
414                                                                       
   H  3-CONHC.sub.2 H.sub.4 OCH.sub.3                                     
                   CH.sub.3                                               
                      CH.sub.3                                            
                         C.sub.2 H.sub.4 OCH.sub.3                        
                                C.sub.2 H.sub.4 OCH.sub.3                 
                                       red                                
415                                                                       
   H  &#34;            CH.sub.3                                               
                      CH.sub.3                                            
                         &#34;      &#34;      red                                
416                                                                       
   H  3-CONH(CH).sub.3 OCH.sub.3                                          
                   CH.sub.3                                               
                      CH.sub.3                                            
                         C.sub.2 H.sub.5                                  
                                C.sub.2 H.sub.5                           
                                       red                                
417                                                                       
   H  4-C.sub.6 H.sub.5 O(CH.sub.2).sub.3 NHCO                            
                   &#34;  CH.sub.3                                            
                         H      C.sub.4 H.sub.9                           
                                       red                                
418                                                                       
   H  4-C.sub.2 H.sub.5 O.sub.2 C                                         
                   CH.sub.3                                               
                      CH.sub.3                                            
                         C.sub.2 H.sub.5                                  
                                C.sub.2 H.sub.5                           
                                       dark                               
                                       red                                
419                                                                       
   H  4-C.sub.2 H.sub.5 O.sub.2 C                                         
                   CH.sub.3                                               
                      CH.sub.3                                            
                         H      C.sub.4 H.sub.9                           
                                       red                                
420                                                                       
   H  4-CH.sub.3 O(CH.sub.2).sub.2 NHCO                                   
                   CH.sub.3                                               
                      CH.sub.3                                            
                         (CH.sub.2).sub.2 OCH.sub.3                       
                                (CH.sub.2).sub.2 OCH.sub.3                
                                       red                                
421                                                                       
   H  4-C.sub.2 H.sub.5 O.sub.2 C                                         
                   CH.sub.3                                               
                      CH.sub.3                                            
                         (CH.sub.2).sub.2 OCH.sub.3                       
                                &#34;      dark                               
                                       red                                
422                                                                       
   H  &#34;            CH.sub.3                                               
                      CH.sub.3                                            
                         (CH.sub.2).sub.3 OCH.sub.3                       
                                (CH.sub.2).sub.3 OCH.sub.3                
                                       &#34;                                  
423                                                                       
   H  4-CH.sub.3 O(CH.sub.2).sub.2 NHCO                                   
                   CH.sub.3                                               
                      CH.sub.3                                            
                         (CH.sub.2).sub.3 OCH.sub.3                       
                                (CH.sub.2).sub.3 OCH.sub.3                
                                       red                                
424                                                                       
   H  4-C.sub.3 H.sub.7 (n)O.sub.2 C                                      
                   CH.sub.3                                               
                      CH.sub.3                                            
                         C.sub.2 H.sub.5                                  
                                C.sub.2 H.sub.5                           
                                       red                                
425                                                                       
   H  4-C.sub.3 H.sub.7 (i)O.sub.2 C                                      
                   CH.sub.3                                               
                      CH.sub.3                                            
                         C.sub.2 H.sub.5                                  
                                C.sub.2 H.sub.5                           
                                       red                                
426                                                                       
   H  3-CONHC.sub.3 H.sub.7 (n)                                           
                   &#34;  &#34;  (CH.sub.2).sub.2 OCH.sub.3                       
                                (CH.sub.2).sub.2 OCH.sub.3                
                                       red                                
427                                                                       
   H  4-CONHC.sub.3 H.sub.7 (n)                                           
                   &#34;  &#34;  &#34;      &#34;      red                                
428                                                                       
   H  4-SO.sub.2 NHC.sub.4 H.sub.9 (n)                                    
                   &#34;  &#34;  C.sub.2 H.sub.5                                  
                                C.sub.2 H.sub.5                           
                                       red                                
429                                                                       
   H  &#34;            &#34;  &#34;  C.sub.3 H.sub.17                                 
                                C.sub.3 H.sub.17                          
                                       red                                
430                                                                       
   H  &#34;            &#34;  &#34;  (CH.sub.2).sub.2 OCH.sub.3                       
                                (CH.sub.2).sub.2 OCH.sub.3                
                                       red                                
431                                                                       
   H  4-SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                 
                   &#34;  &#34;  C.sub.2 H.sub.5                                  
                                C.sub.2 H.sub.5                           
                                       red                                
432                                                                       
   H  &#34;            &#34;  &#34;  (CH.sub.2).sub. 2 OCH.sub.3                      
                                (CH.sub.2).sub.2 OCH.sub.3                
                                       red                                
433                                                                       
   H  &#34;            &#34;  &#34;  (CH.sub.2).sub.3 OCH.sub.3                       
                                (CH.sub.2).sub.3 OCH.sub.3                
                                       red                                
434                                                                       
   H  H            &#34;  &#34;  H      H      red                                
435                                                                       
   H  H            Cl &#34;  (CH.sub.2).sub.2 OCH.sub.3                       
                                (CH.sub.2).sub.2 OCH.sub.3                
                                       red                                
436                                                                       
   H  H            Br &#34;  &#34;      &#34;      red                                
437                                                                       
   H  H            H  &#34;  &#34;      &#34;      red                                
438                                                                       
   H                                                                      
       ##STR340##  H  &#34;  &#34;      &#34;      red                                
439                                                                       
   H                                                                      
       ##STR341##  H  &#34;  &#34;      &#34;      red                                
440                                                                       
   H  &#34;            CH.sub.3                                               
                      CH.sub.3                                            
                         &#34;      &#34;      red                                
__________________________________________________________________________