GB838340A - New monoazo dyestuffs derived from cyanuric chloride - Google Patents

Abstract

The invention comprises dyestuffs of formula <FORM:0838340/IV(c)/1> where A is an aryl group, R is H or alkyl, Y is H or Hlg, X is H, COOH or SO3H and A and X are chosen so that the dyestuff contains at least 2 SO3H groups, or at least 1 COOH and 1 SO3H group. Indicated for A are phenyl, a -and b -naphthyl and diphenyl groups which may be substituted by, e.g., methyl, t-butyl, ethoxy, bromo, chloro, acetamido, sulpho or carboxy groups and especially by SO3H o to the azo group. Methyl is indicated as an alkyl group for R. They are made by reacting at least one mol. proportion of cyanuric chloride with a compound of formula <FORM:0838340/IV(c)/2> The starting dyestuffs may be made by diazotizing appropriate arylamines and coupling in an alkaline medium with the necessary aminonaphthol sulphonic acid which, if the arylamine does not contain an acylamino substituent, may be used in the form of an N-acyl derivative. Specified arylamines are aniline, o-, m- and p-toluidines and anisidines, xylidines, mono- and polychloroanilines, aniline 2-, 3- and 4-sulphonic acids, 3-methyl- and 2,4-dimethyl-aniline-6-, 4 chloro-5-methyl-, 5-chloro-4-methyl- and 4-methyl- and -methoxy-aniline-2-sulphonic acids, aniline-2,5-disulphonic acids, 2,5-dichloraniline-and 2-aminotoluene-4-sulphonic acids, aniline-2-, 3- and 4-carboxylic acids, 4-amino-diphenyl-3- and 41-sulphonic acids, 1- and 2-naphthylamine, 1-naphthylamine-4-, 5-, 6- and 7-mono-and 3,6- and 3,7-disulphonic acids, 2-naphthylamine-1,5-, 4,8-, 6,8-, 5,7- and 3,6-di- and 1,5,7- and 3,6,8-trisulphonic acids. Specified coupling components are 2-amino-, -methylamino-, and -methylamino-1-chloro-, 8-naphthol-6-sulphonic acids, 2-amino-3-carboxy-8-naphthol-6-sulphonic acids and 2-amino-8-naphthol-3,6-disulphonic acid and their corresponding 2-acetyl- and -formamido-compounds. The products may also be made by coupling the diazotized arylamine with the appropriate triazine component. The latter components may be made by condensing cyanuric chloride with the coupling components indicated above. Aqueous media are preferred for the reactions and isolation of the dyestuffs is advantageously effected at pH 6-8, especially at about 6.5 (see Specification 838,337). The dyestuffs, as alkali metal salts, dye silk, wool, regenerated protein and cellulose textile materials, the latter in red shades, in the presence of an acid-binding agent (see Specification 797,946). They also dye silk, wool, regenerated protein, polyamide and modified polyacrylonitrile textile materials by conventional dyeing methods. In examples which illustrate the preparation of the dyestuffs and their use in dyeing processes the components used are chosen from those indicated above, additional diazo components being 4-chloroaniline-2-sulphonic acid, 3-amino-toluene-4-sulphonic acid, 4-chloro-2-aminoanisole-6-sulphonic acid, 6-chloro-2-amino-anisole-4-sulphonic acid, 2 - amino - 21 - methyldiphenylether - 4 - sulphonic acid and dehydrothiotoluidine sulphonic acid.