GB302965A - Improvements in or relating to the manufacture of azo-dyestuffs - Google Patents

Abstract

302,965. Carpmael, A., (I. G. Farbenindustrie Akt.-Ges.). Sept. 22, 1927. Samples furnished. Azo dyes and soluble metal compounds thereof. -Azo dyes, adapted for treatment in substance, or on the fibre during or after the dyeing process, with compounds of metals, such as chromium or copper, are obtained by combining a diazotized 2- aminobenzene-1-carboxylic acid sulphoamide or a derivative or substitution product thereof with a coupling component. The metallic compounds may be used as pigment dyes or for the preparation of size colours. The following examples are specified :-(1) An ammoniacal solution of 2- aminobenzene-1-carboxylic acid - 5 - sulphan-2<1>- anisidide is diazotized and coupled with 1 : 5- naphtholsulphonic acid; the product dyes wool from an acid bath a yellowish red shade which on after-chroming becomes bordeaux red, fast to light, fulling, and carbonizing; the corresponding dyestuff obtained with 2-phenylamino-8-naphthol- 6-sulphonic acid as coupling component dyes wool from an acid bath a reddish brown shade, which on after-chroming becomes black brown. (2) The dyestuff 2-aminobenzene - 1 - carboxylic acid-5- sulphonanilide # (alkaline) the methyl pyrazolone from 2-aminophenol-4-sulpho-6-carboxylic acid dyes wool from an acid bath a reddish yellow shade which on after-chroming or after-coppering becomes greenish yellow. (3) The copper compound of the dyestuff 2-aminobenzene-1-carboxylic acid-5-sulphonamide # (alkaline) 1-acetylamino-8-naphthol-3 : 6-disulphonic acid dyes wool from an acid bath an even wine red shade fast to fulling and light. (4) the copper compound of the dyestuff 2-aminobenzene-1-carboxylic acid- 5-sulphon-4'-toluidide # 2-naphthol-8-sulphonic acid dyes wool from an acid bath an even brownish orange shade; if the coupling component is 1-naphthol-4-sulphonic acid, 2-naphthol- C-sulphonic acid or 1-(4<1>-sulpho)phenyl-3-methyl- 5-pyrazolone the shade is copper red, yellowish red brown, or greenish yellow respectively. (5) The chromium compound of the dyestuff 2-aminobenzene-1-carboxylic acid-5-sulphonamide # 2- aminonaphthalene-7-sulphonic acid, employed as a size colour, gives red violet shades, fast to light; the dyestuff 2-aminobenzene-1-carboxylic acid-5-sulphonanilide # 2-aminonaphthalene-7- sulphonic acid dyes wool from an acid bath reddish orange shades which on after-chroming become bordeaux red, fast to light and fulling; the chromium compound of the dyestuff, used as a size colour gives violet shades, fast to light. 2-Aminobenzene-1-carboxylic acid-5-sulphon-2<1>- anisidide is obtained by treating with o-anisidine in presence of an acid-binding agent the product of reacton of chlorosulphonic acid and o-chlorobenzoic acid, and thereafter replacing the nuclear halogen by the amino group by heating with ammonia under pressure. 2-Aminobenzene-1-carboxylic acid-5-sulphon-4<1> - toluidide, 2 - aminobenzene-1-carboxylic acid-5- sulphonanilide and 2-aminobenzene-1-carboxylic acid-5-sulyhonamide are similarly obtained by using p-toluidine, aniline, and ammonia respectively in place of the o-anisidine.