Patent GB-381767-A (GB)
Title: Manufacture of new azo-dyestuffs
IPC: C09B29/00
Filed: 1931-12-01
Abstract: Azo dyes are made in substance or on the fibre by coupling a diazo or tetrazo compound with an acylated amine made by condensation of a primary aromatic monamine or diamine containing no carboxyl group with an oxycarboxylic acid of the benzene series which is so substituted that it couples with a diazo compound in o-position to the OH group, or by condensation of one molecular proportion of a primary aromatic diamine containing no carboxyl group with one molecular proportion of such an oxycarboxylic acid and one molecular proportion of another aromatic oxycarboxylic acid.  They may be used for dyeing vegetable and animal fibres, lacquers, acetate silk, and regenerated cellulose or for producing lakes.  Fast brown shades are generally obtained.  The arylides may be made by the process of Specification 370,820 from diaminodiphenyls, phenylene- and naphthylenediamines, m : m<1>-azoxyaniline, 3 : 3<1>-diaminobenzoyl-m-phenylenediamine, p - p<1>-diaminoazobenzene, diaminoanthraquinones, 3 : 3<1>- or 2 : 2<1>-dichlorobenzidine, 4 : 4<1> - diaminostilbene, 4 : 4<1> - diaminodiphenylurea, diaminocarbazoles, diaminoacridines, diaminodi- or triphenylmethanes, diaminoacridones, aniline, toluidines, xylidines, naphthylamines, aminonaphthols and their sulphonic acids, dehydrothiotoluidine or a sulphonic acid thereof, aminobenzimidazoles and aminoquinolines. Specified oxycarboxylic acids are p-cresotinic acid, p-oxybenzoic acid, 3-methyl-4-oxy-1-benzoic acid, b -resorcylic acid, b -resorcylic acid-4-monomethyl ether and monobromo - b  - resorcylic acid.  In examples, (1) diazotized 4 - nitro-aniline - 2 - sulphonic acid is coupled with p-cresotinic acid-anilide; the product dyes wool in an acid bath brown tints, which become darker when after-chromed, (2) diazotized m-nitro-p-toluidine is coupled with p-cresotinic acid-o-toluidide, (3) cotton is impregnated with di-(p-cresotinic acid)-dianisidide and developed with a solution of the diazo preparation from 4-chloro-2-aminodiphenylether and naphthalene-1 : 3 : 6-trisulphonic acid, (4) material is padded with di-(p-cresotinic acid)-tolidide and printed with diazotized 1-amino-2 : 5-dichloro-4-benzoylaminobenzene; nitrosamine and diazoamino preparations may be similarly used, (5) woollen thread is grounded with di-(p-cresotinic acid)-benzidide, treated in a bath of diazotized 4-nitro-o-phenetidine and then in a sulphuric acid bath; a dark brown is obtained.  A table showing the shades obtained on the fibre using various diazo components and the following arylides is given: di-(p-cresotinic acid)-dianisidide, benzidide and tolidide, di-(2 : 4-dioxybenzoic acid)-dianisidide, di-(5-bromo-2 : 4-dioxybenzoic acid)-dianisidide, di-(p-cresotinic acid)-p-phenylenediamide, azoxybenzene-m : m<1>-diamide, 1 : 5-naphthylene diamide and 3 : 3<1>-dichlorobenzidide, di-(p-oxybenzoic acid)-benzidide and dianisidide, the mixed diarylide from p-cresotinic acid, 2 : 3-oxynaphthoic acid and dianisidine, the mixed diarylide from o- and p-cresotinic acids and benzidine, and the arylides from p-cresotinic acid and 5-chloro-o-toluidine, J acid, dehydrothiotoluidine - sulphonic acid, a  - naphthylamine, p - phenetidine, dehydrothiotoluidine and 4-amino-1 : 2-methylbenzimidazole.  Specification 357,959 is disclaimed.