DE2752941A1 - Mono:azo dispersion dyes for synthetic fibres - from N-substd. aniline derivs. as coupling components - Google Patents

Abstract

New monoazo dyes are of formula (I). In (I) D is the gp. of a diazo component; R1 is H, Cl, Br, 1-2C alkyl or alkoxy; R2 is as R1, 1-4C alkyl-sulphonyl amino, -alkanoyl amino or -alkoxycarbonyl amino, phenyl sulphoxyl amino or benzoylamino; A1 is a substd. aliphatic or araliphatic gp.; A2 is 2-6C alkylene opt. interrupted by O; A3 is 2-4C alkylene; A4 is 1-4C alkyl; n is 1, 2 or 3. Used as dispersion dyes for hydrophobic fibres, e.g. cellulose acetates, polyamides, and esp. polyesters, and in some cases for use in the process claimed in DT1811796. Good fastness to light, wet treatments and thermofixing is achieved.

Description

Azo dyes

The invention relates to dyes of the general formula I. in which D is the remainder of a diazo component, R1 is hydrogen, ethyl, ethyl, chlorine, 3rom, methoxy or ethoxy, R2 is hydrogen, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, C1-C4-alkylsulfonylamino, C1-C4-alkanoylamino, C1-C4-alkoxycarbonylamino, phenylsulfonylamino or benzoylamino, a substituted aliphatic or araliphatic radical, a C2-C6-alkylene radical which is optionally interrupted by oxygen, a C2-C4-alkylene radical, A4 is C1-C4-alkyl and n is 1, 2 or 3.

The radicals D of the diazo components originate predominantly from the benzene or heterocyclic series, e.g. 3. the thiophene, thiazole, isothiazole, thiadiazole, J3enzthiazole, isothiazole, isothiazolothiophene, 3enzisothiazole, triazole, pyrazole or indazole series. Examples include: aniline, o-, m- or p-toluidine, o-, m- or p-methylsulfonylaniline, o-, m- or p-nitroaniline, o-, m- or p-cyananiline, o-, m- or p-chloroaniline, o-, m- or p-3romaniline, o-, m- or p-trifluoromethylaniline 3,4-dichloroaniline, 2,5-dichloroaniline, 5,5-dichloroaniline, 2,4,5-trichloroaniline, 2,4,6-trichloroaniline, 2,4,6-tribromaniline, 2,4-dicyananiline, 2,5-dicyaniline, 2-cyano-4-chloroaniline, 2-cyano-4,6-dichloroaniline, 2-cyano-4-chloro-6-bromaniline, 2-cyano-4, 6-dibromaniline, 2,4-dicyano-6-chloroaniline, 2-chloro-4-cyananiline, 2-trifluoromethyl-4-chloroaniline, 2-Nitro-4-chloroanil in, 2-tltro-4-methyl-aniline, 2-Nethyl-4-nitroaniline, 2-ethoxy-4-nitroaniline, 2-chloro-4-nitroaniline, 2-bromo-4-nitroaniline, 2-trifluoromethyl-4-nitroaniline, 2-trifluoromethyl-4-nitro-6-bromaniline, 2-trifluoromethyl-4-nitro-6-cyananiline, 2,5-dichloro-4-nitroaniline, 2,6-dichloro-4-nitro-aniline, 2,6-dibromo-4-nitroaniline, 2-chloro-4-nitro-6-bromaniline, 2,6-dichloro-4-cyananiline, 2,4-dinitroaniline, 2,4-dinitro-6-chloroaniline, 2,4-dinitro-6-bromaniline, 2,4-dinitro-6-cyananiline, 2,6-Dicyan-4-nitro-aniline, 2-Nethylsulfonyl-4-chloroaniline, 2-chloro-4-methylsulfonyl-aniline, 2-methyl sulfonyl-4-nitroaniline, 2-nitro-4-ethylsulfonylaniline, 2,4-dinitro-6-methylsulfonylaniline, 2-cyano-4-methylsulfonylaniline, 2-phenylsulfonylaniline, 2-methylsulfonyl-4-nitro-6-bromo-aniline, 2-methylsulfonyl-4-nitro-6-chloro-aniline, 2,6-dichloro-4-methylsulfonyl-aniline, 2,6-dibromo-4-methylsulfonylaniline, o-, m- or p-aminobenzoic acid methyl ester, ethyl ester, propyl ester, -butyl ester, -benzyl ester, -phenylethyl ester, -phenoxyethyl ester, -phenoxyethoxyethyl ester, -phenyl ester, -S-methoxyethyl ester, -ß-ethoxyethyl ester, -ß-hydroxyethyl ester, 4-nitroanthranilic acid methyl ester, methoxyethyl ester, 3- or 4-aminophthalic acid; 5-aminoisophthalic acid or aminoterephthalic acid dimethyl ester, diethyl ester, 3- or 4-aminobenzoic acid amide, methyl amide, n-butyl amide, methoxypropyl amide, 2-, 3- or 4-aminobenzoic acid dimethylamide, diethylamide, pyrrolidide, morpholide, -N-methyl-N-ß-hydroxy-ethylamide, -phenyläthylamid, -phenoxypropylamid, -phenoxyäthoxypropylamid, 5-Aminoisophthalic acid diamide, -dimethoxypropylamide, aminoterephthalic acid-bis-diethylamide, 3- or 4-aminophthalic acid imide, -ß-hydroxyethylimide, -phenylimide, 3-amino-6-nitro-phthalic acid-ß-hydroxyethylimide, 2-, 3- or 4-aminobenzenesulphonic acid dimethylamide, -morpholide, -N-methylanilide, 1-amino-2-chlorobenzene-4-sulphonic acid dimethylamide, 1-mino-2,5- or 2,6-dichlorobenzene-4-sulfonic acid dimethyla = id, methyl sulfonic acid-2'-, 3'- or 4'-aminophenyl ester, benzenesulfonic acid 2'-, 3'- or 4'-aminophenyl ester, B-acetyl-pphenylenediamine, 2-aminobenzophenone, 1-aminoanthraquinone, 1-amino-4-chloroanthraquinone, 1-amino-2-ethoxynaphthalene, 4-amino-naphthalic acid butylimide, 6-amino-5,7-dicyanindane, 4-aminoazobenzene, 2 ', 3-dimethyl-4-aminoazobenzene, 3', 2-dimethyl-4-amino-azobenzene, 2-methyl-5-methoxy-4-aminoazobenzene, 4-amino-2-nitroazobenzene, 2,5-dimethoxy-4-aminoazobenzene, 4'-hydroxy-4-aminoazobenzene, 4 4'-chloro-4-aminoazobenzene, 2,3'-dichloroanimoazobenzene, 3,5-dibromo-4-amino-azobenzene, 4-aminoazobenzene-4'-sulfonic acid dimethylamide, 2'- or 3'-chloro-4-aminoazobenzene, benzolazo -4-aminonaphthalene, 3-amino-2,1-benzisothiazole, 3-amino-5-chloro-2,1-benzisothiazole, 3-amino-5-bromo-2,1-benzisothiazole, 3-amino-5-nitro-2,1-benzisothiazole, 3-Amino-5-nitro-7-chloro-2,1-benzisothiazole, 3-Amino-5-nitro-7-bromo-2,1-benzisothiazole, 3-Amino-5,7-dichlorobenzisothiazole, 3-Amino-5,7-dibromo-benzisothiazole, 4-Amino-7-nitro-1,2-benzisothiazole, 4-amino-5-chloro-7-nitro-1,2-benzisothiazole, 4-amino-5-bromo-7-nitro-1,2-benzisothiazole, 4-Amino-5-cyano-7-nitro-1,2-benzisothiazole, 2-aminothiazole, 2-amino-5-nitrothiazole, 2-amino-4-methyl-5-nitro-thiazole, 2-amino-4-phenyl-5-nitrothiazole, 2-amino-5-phenyl-1,3,4-thiadiazole, 2-Amino-5-ethylmercapto-1,3,4-thiadiazole, 3-phenyl-5-amino-1,2,4-thiadiazole, 3-ß-carbomethoxyethylmercapto-5-amino-1,2,4-thiadiazole, 3- (methyl, ethyl, 3utyl or benzyl) mercapto-5-amino-1,2,4-thiadiazole, 3-aminopyrazole, 3-Amino-4-cyanpyrazole, 2-phenyl-3-amino-4-cyanpyrazole, 5-amino-5- (methyl-, ethyl-, phenyl or benzyl) pyrazole, 3-amino-l, 2,4-triazole, 3-mnino-5- (methyl-, ethyl-, phenyl- or benzyl) -1,2,4-triazole, 3-amino-1-phenyl-pyrazole, 3-minopyridine, 3-aminoquinoline, 2-aminobenzothiazole, 2-amino-6-methylbenzthiazole, 2-amino-6- (methoxy-, ethoxy- or butoxy) benzothiazole, 2-amino-6-cyanobenzothiazole, 2-amino-6-thiocyanato-benzothiazole, 2-amino-6-nitrobenzthiazole, 2-amino-4-cyano-6-nitrobenzthiazole, 2-amino-4,6-dinitrobenzthiazole, 2-amino-5,6-dichlorobenzothiazole, 2-amino-6,7-dichlorobenzothiazole, 2-mnino- (4 or 6) -methylsulfonylbenzthiazole, 3-amino-5-nitro-isothiazolothiophene, 2-amino-3-nitro-5-methylsulfonylthiophene, 2-amino-3,5-bis (methyl-sulfonyl) -thiophene, 2-amino-3,5-dinitrothiophene, 2-amino-3-cyano-5-nitro-thiophene, 2-amino-5-nitrothiophene or 5-amino-3-methyl-isothiazole.

R radicals are in addition to those already mentioned in detail z. E.g .: methyl sulfonylamino, ethylsulfonylamino, formylamino, acetylamino, propionylamino, methoxycarbonylamino, Ethoxycarbonylamino or butoxycarbonylamino.

Remainder. A1 are, for example, C1-C4-alkyl, which is replaced by chlorine, bromine, hydroxy, Cyano, C1-C4-alkoxy, phenoxy, C1-C4-alkanoylamino, C1-C4-alkanoyloxy, benzoyloxy, C1-C4-likoxycarbonyl or phenyl is substituted.

Examples include: chloroethyl, bromoethyl, Cyanoethyl, benzyl, phenylethyl, 3-phenylpropyl, 2-phenylpropyl, hydroxyethyl, 2-phenyl-2-hydroxyethyl, 2-hydroxy-3-chloropropyl, 2,3-dihydroxypropyl, 2-hydrorypropyl, 2-hydroxybutyl, 2-hydroxy-3-methoxypropyl, 3-hydroxypropyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-butoxyethyl, 2-phenoxyethyl, 2-phenoxypropyl, 2-acetylaminoethyl, 2-acetylaminopropyl, 2-propionylaminoethyl, 2-benzoyloxyethyl, 2-acetoxyethyl, 2-propionyloxyethyl, 2-butyryloxyethyl, 2-isobutyryloxyethyl, Benzoyloxyethyl, methoxycarbonylethyl, ethoxycarbonylethyl, propoxycarbonylethyl, Butoxycarbonylethyl, methoxyethoxycarbonylethyl, isopropoxycarbonylethyl or isobutyryloxycarbonylethyl.

The residues A2 are, for. E.g .: -CH2CH2-, -CH2CHCH3, -CH2CHC2H5 or -C2H4OC2H4- to to name.

Examples of radicals A3 are: -CH2-CH2-, -CH2CHCH3 or -CH2CHC2H5.

Remnants A4 are z. 3.1 methyl, ethyl, propyl, isopropyl, butyl or Isobutyl.

To prepare the dyes of the formula I, a diazonium compound of amines of the formula II D-NH2 II can be used with a coupling component of the formula III realize. Diazotization and coupling have no special features compared to known processes.

Compounds of the formula III are obtained from compounds of the formula by reaction with compounds of the formula The reactions are expediently carried out in aprotic solvents in the presence of a base, e.g. B. pyridine made.

Dyes of the formula Ia are of particular importance in which R3 is hydrogen, methyl or methoxy, R4 is hydrogen, methyl, nethoxy, chlorine, Icetyiaaino or propionylamino, A5 ß-hydroxyethyl or -propyl, ß-cyanoethyl, ß-C1- to C4-alkoxyethyl or -propyl, phenoxyethyl or -propyl , ß-C2- to C4-alkanoyloxyethyl or -propyl, ß-C1- to C4-alkoxycarbonylethyl or -propyl, benzyl or phenylethyl, A6 -CH2CH2-, -CH2CH-CH3 or -CH2-CHC2H5, A7 -CH2CH2- or - CH2-CH-CH3, A8 C1-C4-alkyl and n are 1 or 2 and D is as defined.

The radicals D are preferably derived from the benzene, thiophene, thiazole, Thiadiazole, bensthiazole, benzisothiazole or azobenzene series.

Preferred diazo components are, for example, those of the formula in which T is hydrogen, chlorine, bromine, nitro, cyano, methylsulfonyl, ethyl sulfonyl, phenylsulfonyl or C1 to C4 alkoxy carbonyl, T2 nitro, cyano, hydrogen, chlorine, bromine, methylsulfonyl, ethyl sulfonyl, phenylsulfonyl or phenylazo and T3 hydrogen, Are chlorine, bromine, nitro or cyano, and 2-amino-5-nitrothiophene, 2-amino-3,5-dinitrothiophene, 2-amino-3-cyano-5-nitrothiophene, 2-amino-3-nitro-5-methylsulfonylthiophene , 3-Amino-5-chloro-2,1-benzisothiazole, 3-amino-5-bromo-2,1-benzisothiazole, 3-amino-5-nitro-2,1-benzisothiazole, 3-amino-5-nitro -7-chloro-2,1-benzisothiazole, 3-amino-5-nitro-7-bromo-benzisothiazole, 4-amino-7-nitro-1,2-benzisothiazole, 4-amino-5-chloro-7-nitro -1,2-benzisothiazole, 4-amino-5-bromo-7-nitro-1,2-benzisothiazole, 4-amino-5-cyano-7-nitro-1,2-benzisothiazole, 2-amino-5-nitrothiazole , 2-amino-5-ethylmercapto-1,3,4-thiadiazole, 3-phenyl-5-amino-1,2,4-thiadiazole, 3-β-carbomethoxyethylmercapto-5-amino-1,2,4-thiadiazole , 3-methylmercapto-5-amino-1,2,4-thiadiazole, 2-amino-6-methoxybenzthiaz ol, 2-amino-6-cyanobenzothiazole, 2-amino-6-thiocyanatobenzothiazole, 2-Mnino-6-nitrobenzthiazole, 2-amino-4-cyano-6-nitrobenzthiazole, 2-amino-4,6-dinitrobenzthiazole, 2- Amino-5,6-dichlorobenzothiazole, 2-amino-6,7-dichlorobenzothiazole or 2-amino-6-methylsulfonylbenzthiazole.

The dyes of the formula I are suitable for dyeing synthetic ones and semi-synthetic fibers, e.g. B. cellulose acetates and polyamides in particular Polyesters. The dyeings obtained have good light, wet fastness and heat setting fastness properties.

Some of the dyes are also for that in the German patent 1 811 796 is suitable.

In the following examples, parts and percentages relate to unless otherwise noted, by weight.

Example 1 10.4 parts of 2,6-dichloro-4-nitroaniline are in 50 parts Dissolved 85% sulfuric acid and at 0 - 5 OC with 16 parts 45 pointers nitrosylsulphurous acid diazotized. After 5 hours, the diazo solution thus obtained is left at 0-5 ° C. in a solution of 14.6 parts of N-cyanoethyl-N- (ß-methoxyäthoxycarbonyloxäthyl) aniline pour in 30 parts of concentrated hydrochloric acid, 250 parts of water and 250 parts of ice. A pH of 1.0 is set by adding sodium acetate. After finished Coupling, the precipitated dye is filtered off with suction and washed neutral with water and dried under reduced pressure at 60.degree.

22.5 parts of the dye of the formula are obtained which provides yellow-brown dyeings with good fastness properties on polyester fibers.

Example 2 13.7 parts of 4-amino-5-bromo-7-nitro-1,2-benzisothiazole dissolved at 10-15 ° C in 100 parts of 96 pointer sulfuric acid. Then you give gradually at 0 - 5 ° C 30 parts of a glacial acetic acid / propionic acid mixture (17: 3) and diazotized at 0 - 5 ° C by adding dropwise 15 parts of 45 pointer nitrosylsulfuric acid. Man stir for 5 hours at 0-5 ° C. and allow the slide solution to form a mixture 17.9 parts of N-phenylethyl-N- (ß-methoxyethoxycarbonyloxäthyl) -m-toluidine, 40 parts Dimethylformamide, 40 parts of concentrated hydrochloric acid, 250 parts of water, 250 parts Ice and 1 part sulfamic acid flow.

After the coupling has ended, the dyestuff which has precipitated out is filtered off with suction, washed neutral with water and dried under reduced pressure at 70.degree. 27 parts of the dye of the formula are obtained which provides blue dyeings with good fastness properties on polyester fibers.

Example 3 A solution of 9.8 parts of p-4minoazobenzene in 125 parts of glacial acetic acid is poured, with vigorous stirring, into a mixture of 12.5 parts of concentrated hydrochloric acid, 20 parts of water and 75 parts of ice, and a solution of 3, 5 parts of sodium nitrite in 12.5 parts of water. After three hours of stirring at 0-5 ° C., any excess sodium nitrite that may be present is destroyed by adding a little sulfamic acid. The diazonium salt solution is filtered and allowed to flow at 0-5 ° C. to a mixture of 14.6 parts of N-cyanoethyl-N- (B-methoxyethoxyearbonyloxäthyl) aniline in 30 parts of concentrated hydrochloric acid, 250 parts of water and 250 parts of ice. After the coupling has ended, the dyestuff which has precipitated out is filtered off with suction, washed neutral with water and dried at 50.degree. C. under reduced pressure. 17.5 parts of the dye of the formula are obtained which delivers intense orange shades with good fastness properties on polyester and cellulose esters.

Example 4 6.9 parts of p-nitroaniline are introduced into 20 parts of water and 25 parts of concentrated hydrochloric acid with stirring, the mixture is stirred for one hour at room temperature and 70 parts of ice are added. A solution of 3.5 parts of sodium nitrite in 12.5 parts is then added dropwise Add water and stir at 0-5 ° C. for 2 hours. Any excess sodium nitrite is destroyed by adding a little sulfamic acid and the diazonium salt solution is filtered. A solution of 17.8 parts of 1- [N-cyanoethyl-N- (ß-methoxyethoxycarbonyloxethyl) -smini-3-acetylaminobenzene in 40 parts of glacial acetic acid is added dropwise to the diazonium salt solution in the course of 2 hours at 0-5 ° C. After the coupling has ended, the dyestuff which has precipitated out is filtered off with suction, washed neutral with water and dried at 50 ° C. under reduced pressure. 20.8 parts of the dye of the formula are obtained which provides intense red shades with good fastness properties on polyesters.

Example 5 8.6 parts of 2-chloro-4-nitroaniline are introduced into a solution of 12.5 parts of concentrated hydrochloric acid and 50 parts of water, the mixture is stirred for one hour at room temperature and 100 parts of ice are then added dropwise to a solution of 3, 5 parts of sodium nitrite in 12.5 parts of water are added and the mixture is stirred at 0-5 ° C. for 3 hours. Any excess of sodium nitrite that may be present is destroyed by adding a little sulfamic acid, the diazonium salt solution is filtered and at 0 - 5 0 in a mixture of 15.3 parts of N-cyanoethyl-N- (ß-ethoxyethoxycarbonyloxethyl) aniline in 30 parts of concentrated hydrochloric acid, 250 parts of water and 250 parts of ice are poured in. After the coupling has ended, the dyestuff which has precipitated out is filtered off with suction, washed neutral with water and dried under reduced pressure at 50.degree. 18.5 parts of the dye of the formula are obtained which delivers intense scarlet tones with good fastness properties on polyesters and cellulose esters.

Finely divided dye which can be easily stirred into aqueous dye liquors Preparations can be obtained, for example, as follows: The dye (dried dye or moist pressed material) is in the presence of dispersants at temperatures of 40 - 110 OC, preferably at 60 - 90 OC, ground. Pre-treatment is also advantageous, z. B. heating in aqueous suspension or as a water-moist paste, if necessary with the addition of dispersants and / or organic solvents to temperatures from 50 to 120 OC.

EXAMPLE 6 7.2 parts of 2-amino-5-nitrothiazole are introduced into 20 parts of 96% strength sulfuric acid at 10 to 15 ° C., 100 parts of a mixture of glacial acetic acid and propionic acid (17: 3) are slowly added at this temperature at 0 - 5 ° C. with 15 parts of 45 pointer nitrosylsulfuric acid diazotized. After 4 hours, the diazo solution thus obtained is added dropwise at 0-5 ° C. to a solution of 14.6 parts of N-cyanoethyl-N- (β-methoxyethoxycarbonyloxethyl) aniline in 30 parts of concentrated hydrochloric acid, 250 parts of water and 250 parts of ice. A pE value of 1.3 is set by adding sodium acetate. After the coupling has ended, the dyestuff which has precipitated out is filtered off with suction, washed neutral with water and dried at 50.degree. C. under reduced pressure. 13.8 parts of the dye of the formula are obtained which provides violet shades with good fastness properties on polyesters and cellulose esters.

Analogously to the methods described, the dyes, characterized in the following examples by specifying the substituents, are obtained which produce dyeings in the specified hue on polyester fibers. Example D R1 R2 Ä2 n shade 7 NH2 HH C2H4OCH3 2H4 0 2H4 1 OH3 orange Cl n NCNH2 Z OH3 C2H4CN 1 02115 1 M. 9 = NH2 = = h = = OH3 m rC \ rh "K \ XK \ 4 rr \ ao OC) II o '3 = ~ a. ~ ~ ~ 25 + <cz W. m OCH3 n W. Cl <C) HC) UE ^ Õ o C) S o «Mmmmi zm mm ~ mmmmmmmm NC ^ 4 N iN iN i mn z; H GO ROOO m HF as o ~ cu n * @ ~ ~ ~ r ~ Pl Example D R1 R2 ii 3 n 6 shade Cl 15 02NNH2 H OH3 C2H4CN C2H4 C2H4 1 CH3 scarlet 16 H CCH3 II II 1 red 0 oh ° hhs n mn om = co m oC4 m ooJ 17 O2N? Ffl2 H OH3 II I1 1 1 C2H5 scarlet 18 rr H NHCCH3 II r 1 CH3 red 0 n cq M CV 4 otet = = 20 N OH3 II 1 OH3 CM a; q 0 4 otrt = = o rn n C) = OFC) = O n mmmmmmmmm 42 m ¢ N Example 3) R1 R2 A1 Ä2 3 n 14 color tone SO2CR3 C. E cd cd ok n 02N NH2 HHPP c, rci ri <d rc d OO h O h ° <do o> kk Fr k hO PP t10 = 25 UE H C113 1 1 1 CH3 brown = t N \ I cu X cu u = U = '3 = = Br cu tul n mN = UO or 0 28% NNII2 HH 0 2H4CN 1I 1 yellow-brown cu cu X U = = = = U O N = 1 1 Z o 2 5 mmwm v NNNN to Nx mmmmmmm ~ mwmmwmm n m C) NNNN oN Z; i Z hhih R 9V VV NNNN OOOO P. tn H na LN \ 0> ONNNNN az 0E A1 NN a # H p oa, CM h o h 31 cr \ WMP: ut OUU a ~. ~ ~ ~ W. K \ cu rA N Cl 33 cu MH2 OCH3 NHC1-C2H5 CH2 1I 1 CH3 1 NN NO2 O UOOU ct NNN m N q OOOOO UE mn mN mn cJo 0s0 cz = o Nx mi U.N »^ M mm - m 0 ° Õ 0o H i Z hi O iN N 0t0 AtZ NNN ~ OOO P. m GD no F n Example D R1 R2 A1 A2 A3 n A4 color tone 4th + Z rl O 7th <d 5: ri o 36 m = OH3 = u 3 ON 37 O2NN1I2 H NHC11-CH3 0 2H40N I1 I1 1 1 N C) = = = = sir N = = = Rome sr 39 II II o 2H4CN o II 1 O wç mt x NNNNN y nn C) = O n mmmmm N NN t Z iu Z i oN Z tN t C O ON UE \ 0 tv 40 I3S 2 4 C2H4 CH 1 CH red oh ~ R UE n: n t4 t HH ~ N 24 42 w N u cu <OO z S = uut 43 HH I1 1 II cu cu cu uott 54 QQ p ou w uu NH2 o lt C II t C2H5 red-violet N «Mmm M m N Pt tq MX Pt s E r 15 N CX SO <O ~ 0F + P1 Example D R1 R2 A1 A2 A3 n A4 color tone O i rl u, o 45 O2NNH II i A @ o <d ri ko 15 weeks m 1I N Cl 47) N & = = = = C) with N m Cl C) = = = = = d H u I1 II red o NH2 W 31 cu cu cu K \ 25th wmmmwm IN AND NN m S ZR t Õ cz HH oou N O u 0 ts 08 0 ny oo «OHO 51 O2NH2 H lt C2lt4 = 2 = 3 rn M w W c mm CQ o = eo 52 O2N Nlt2 lt CH3 C2H4OCH3 I1 1 1 blue e : nw cu <1 O = = - =: 1 od- CM CM MHC11-CH3 C2lt40N 1 - NH * + * + u a ct t OUO lt CH3 = OO = IV 2 n n OtO n N O2N 'NH2 lt Cl C2H4OH = i Õ Õ 2H5 red-violet X mmmmmm N m NN ZO Sq N } NZN CO trt RRN $ » NUN OOO m ~ i ~ N tN * UO xD \ oo UO o 1S to Example D R1 R2 A1 A2 A3 n A4 color tone +>< r cr a> a, rc O GD * e> 57> H OH3 OH4 C2H4 0 2H4 1 OH3 purple o + r cd do rc > S »= = = - rn H = = oo - c) 58 II HH C2 3r W. cu O = = = = = = en cu ;) = = = ~ = = ? 0t Q 9, M. X 62 UHHO 2H4O0H3 U 2 II 63 w> mmmw mmmmmmm NN ihi NN OO FX 0 \ 0 v N 1 « n SES CN 64 rl - = fo For rc PP nt pn 65 1I H ¢ oN õ ~ a VN Õ WOW tt cv express 66 rrr C2H4OC.CH3 rrr CH3 r 0 67 2 H CH3 C2H4 1 1I II cu <O = rn Pt u 69 HH C2H4CN tt 1 C2H5 = U ~ 0 c 70 xR H 1iHCuC2H5 »+ + w CH3 blue 5 (oouu (U tuo 4 o uo u rn oso n Nx Õ: t CH2CHCH3 CH2CHCH3 õ i I1 II ~ NX en xx en m N i A ON SN 0N ~ I + ç F as o ~ N Example D R1 R2 A1 A2 A3 n A4 color tone dm H 0113 0 H OCH 0 H 0 11 1 0 H blue d 3 24 24 49 o N 2 P NH2 Cl mç m - RH 0 H ON 0 H 0 H 1 OH blue-violet cz = = = = = NH2 rvv N ~ Br 76 02Ä <N. H 1 1 II II 1 1I II cu u uu = = = =. = = 1 s: 77 II N 24 O = = = = = = MQO s o II o 2H4 2 mç mmm mv mw tL1 WWW 79 II O = II II = as per dd K \ M 80 m o a mmmmmmmm Z j ZjN ZoZ 5 NNN OOO n ¢ un V) ru a) ao o

Claims (4)

Claims 1. Azo dyes of the general formula I in the D is the remainder of a diazo component, R1 is hydrogen, methyl, ethyl, chlorine, bromine, methoxy or ethoxy, R2 is hydrogen, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, C1-C4-alkylsulfonylamino, C1-C4-alkanoylamino, C1- C4-alkoxycarbonylamino, phenylsulfonylamino or benzoylamino, A1 a substituted aliphatic or araliphatic radical, A2 a C2-C6-alkylene radical optionally interrupted by oxygen, A3 a C2-C4-alkylene radical, 4 A C1-C4-alkyl and n 1, 2 or 3 mean. 2. Dyestuffs according to Claim 1 of the formula Ia in which R5 is hydrogen, methyl or methoxy, R4 is hydrogen, methyl, methoxy, chlorine, acetylamino or propionylamino, A5 ß-hydroxyethyl or -propyl, ß-cyanoethyl, ß-C1 - to C4-alkoxyethyl or -propyl, phenoxyethyl or -propyl , ß-C2 - to C4-alkanoyloxyethyl or -propyl, ß-C1- to C4-alkoxycarbonylethyl or -propyl, benzyl or phenylethyl. 0 @ 7 - @@ 2 @@ 2-, - @@ 2 @@ - @@ 3 or - @@ 2 - @@@ 2 @ 5, A7 -CH2CH2- or -CH2-, CH-CH3, A8 is A @ C1-C4-alkyl and n is 1 or 2 and D is as defined. 3. Process for the preparation of dyes according to Claim 1, characterized in that a diazonium compound of amines of the formula II D-NH2 II is reacted with a coupling component of the formula III. 4. Use of the dyestuffs according to Claim 1 for dyeing textile material made of polyesters.