GB433878A - The manufacture of water-soluble diazoamino compounds and of water-insoluble azodyestuffs derived therefrom - Google Patents

Abstract

Diazoamino compounds are made by reacting upon a diazo compound of an amine containing as substituent a solubilizing group with a primary amine containing no solubilizing group, the two components being selected in such a manner that the diazo component is more strongly negatively substituted than the primary amine. On acid treatment the diazo compound of the primary amine containing no solubilizing groups is obtained. In examples: (1) diazotized 4-sulpho-2-anthranilic acid is condensed with p-toluidine; (2) diazotized aniline-2 : 5-disulphonic acid with 5-chloro-2-toluidine; (3) diazotized 4-nitroaniline-2-sulphonic acid with 3-nitraniline. Diazoamino compounds from the following additional components are also specified: aniline-2- or 4-sulphonic acid, 5-sulpho-2-anthranilic acid, 5-sulpho-3-carboxyaniline, aniline-2 : 4- or 3 : 5-disulphonic acid, 2-aminotoluene-4 : 5-disulphonic acid, 1-naphthylamine-3 : 6 : 8-trisulphonic acid, 4-nitraniline-2-sulphonic acid, 2-nitraniline-4-sulphonic acid, 5-chloraniline-2-sulphonic acid; 3- or 4-chloraniline, 2 : 4-dimethylaniline, 4-chlor-2-toluidine, 2 : 4 : 5-trimethylaniline, 4-anisidine, 2-chloraniline, 2 : 5 - dichloraniline, 5 - nitro - 2 - toluidine, 4-chloro-2-anisidine. Azo dyes insoluble in water are made by coupling a component containing no solubilizing group with a diazo compound prepared by the action of an acid or an acid-reacting agent on the above diazoamino compounds. They may be prepared in substance or on a substratum, in particular vegetable fibre or in a printing process. In examples: (4) the diazoamino compound from diazotized aniline-2-sulphonic acid and 3-chloraniline and 2-(2<1> : 3<1>-hydroxynaphthoylamino)-1-methylbenzene are dissolved in caustic soda and turkey red oil, the thickened mixture printed on cotton and the print developed by passing through a bath of acetic acid, formic acid and Glauber;s salt: (5) cotton is printed with a mixture of the diazoamino compound from diazobenzene-2 : 5-disulphonic acid and 5 - chlor - 2 - toluidine and 2-(2<1> : 3<1>-hydroxynaphthoylamino)-1-methyl-5-methoxybenzene and the print developed by treating with steam containing acetic and formic acid. A table is given showing the shades obtained by use of the above-mentioned diazoamino compounds and the following components: the 2<1> : 3<1>-hydroxynaphthoyl derivatives of 2-toluidine, aniline and 2-amino-1-methyl - 5 - methoxybenzene, diacetoacetyl-o-tolidine, 1 - (2<1> : 3<1> - hydroxycarbazolecarboylamino)-4-chlorbenzene. Specification 324,041, [Class 2 (iii)], is referred to.