GB259970A - The manufacture of new azo dyestuffs - Google Patents

Abstract

259,970. I. G. Farbeninsdustrie Akt.- Ges., (Assignees of Farbenfabriken vorm. F. Bayer & Co.). Oct. 14, 1925, [Convention date]. Trisazo dyes are made by coupling an aminoazo compound, obtained from a p-nitramine or a.cidvlp-diamine or a derivative thereof and a diazotizable second component, with a derivative of an aminonaphthol sulphonic acid containing a free heteronuclear amino-group, further diazotizing the resulting disazo dyestuffs and coupling with methylketol or 1-phenyl-3-methyl-5-pyrazolone, or a derivative thereof, and finally splitting off the acidyl group or reducing the nitro group of the starting component. The product's give direct dyeings in green shades which can be diazotized on the fibre and developed with #-naphthol or 1-phenyl-3-methyl-5-pyrazolone. The preparation of dyestuffs from the following components is described in examples :-(1) 4-acetylaminoaniline- 2-sulphonic acid # 1 :2-aminonaphtholethylether-6-sulphonic acid # p-aminobenzoyl-2- amino-5- (or 8) naphthol-7 (or 6) sulphonic acid i # 1-phenyl-3-methyl-5-pyrazolone or methylketol. (2) 1 : 4-acetylnaphthylenediamine-6-sulphonic acid # 1 : 6-naphthylamine sulphonic acid # p-aminobenzoyl-1-amino-8-naphthol-4- sulphonic acid # 1-phenyl-3-methyl-5-pyrazolone, (3) 4-oxalylaminoaniline-3-sulphonic acid # 1 : 2-aminonaphtholether # m or p-aminophenyl-1 : 2-naphthimidazole-5- oxy - 7 - sulphonic acid # methylketol. Other acidylated pphenylene- or naphthalene-diamines or their halogen, oxalkyl, sulphonic or carboxylic acid derivatives may be used as first components, and aminocresolether, alpha-naphthylamine and its 6- or 7-sulphonic acids, 1:5: 7-aminonaphthol-sulphonic acid. and 1 : 2-aminonaphtholether and its sulphonic acids may be used as second components, the ethers being preferably employed when the first component is of the benzene series, and alpha-naphthylamine derivatives when it is of the naphthalene series. As third components other derivatives of 2 :5-, 2:8-, or 1 : 8-aminonaphtholmono- or di-sulphonic acids containing free heteronuclear amino groups may be used, e.g. the aminobenzoyl, aminophenyl-naphthimidazole, and aminonaphthothiazole derivatives of these acids. Specification 974/11 is referred to. p-Aminobenzoyl-1-amino-8-naphtol-4-sulphonic acid is prepared by the action of p-nitrobenzoyl chloride on 1-amino-8-naphthol-4-sulphonic acid in weakly alkaline solution and reducing the product with iron in acetic acid solution.