GB554201A - New monoazo dyestuffs - Google Patents

Abstract

554,201. Dyes. KNIGHT, A. H., STEPHEN, W. E., and IMPERIAL CHEMICAL INDUSTRIES, Ltd. Dec. 17, 1941, No. 16275. [Class 2 (iii)] Monoazo dyes, suitable for colouring animal fibres, e.g. wool or silk, and dyeing wool from an acid bath brown shades, fast to severe washing and milling and to light, are obtained by diazotizing an amine of the general formula X-CO-NY-R-NH 2 , wherein R represents a m- or p-phenylene residue, which may be substituted, e.g. by methyl, methoxy or sulphonic acid groups, X represents a monochloro- or monobromo-alkyl (C 1 to C 3 ) group and Y represents H, unsubstituted alkyl (C, to C 6 ), cycloalkyl, aralkyl, alkoxyalkyl or aryl, and coupling in an alkaline, neutral or acid medium with N-phenyl-2-amino-8-naphthol-6-sulphonic acid or a derivative thereof substituted in the phenyl nucleus. Specified diazo components are the N-ethyl, N-isopropyl, N-n-butyl, N-sec.- butyl, N-cyclohexyl, N-o- or p-methylcyclohexyl, N-benzyl, N-#-methoxyethyl, N-#- ethoxyethyl and N-phenyl derivatives of 4- amino-chloroacetanilide, the N-benzyl derivative of 3-amino-chloroacetanilide, the N- ethyl, N-isopropyl and N-cyclohexyl derivatives of 4-amino-#-chloropropionanilide, the 2-N- ethyl derivative of 4-amino-2-N-chloroaceltoluidide, 4-amino-2-N-#-chloro- or bromopropriontoluidide and 4-amino-2-N-α-bromo propiontoluidide, 4-amino-2-N-benzyl-chloroacettoluidide, 4-amino-2-N-benzyl-chloroacetanisidide, 2-amino-4- or 5-N-ethyl-chloroacettoluidide, 5-amino-2-N-cyclohexyl-chloracettoluidide, 4-amino-2-N-ethyl-α-bromobutyr- or isobutyr-toluidide, 3-amino-chloroacet- or #- chloropropion-anilide-4-sulphonic acid and 4- amino - chloroacetanilide - 3 - sulphonic acid. Specified coupling components are N-phenyl-2- amino-8-naphthol-6-sulphonic acid and its o-, m- or p-methyl, o-methoxy, p-methoxy or ethoxy, o-, m- or p-chloro, p-carboxy and p- (N-ethyl-N-acetyl) amino derivatives. Examples relate to the production of the dyestuffs, (1) 4-amino-N-ethyl-chloroacetanilide # (acid or alkaline) N-phenyl-2:8:6-acid, (2) and (3) 4-amino-2-N-ethyl-chloroacettoluidide # (2) acid, (3) alkaline) N-p-methoxyphenyl-2:8:6- acid, (4) 4-amino-N-cyclohexyl-chloroacetanilide # (alkaline) N-p-methyl- or o-methoxyphenyl-2:8:6-acid, (5) 4-amino-N-ethyl-chloropropionanilide # (alkaline) N-phenyl-2:8:6- acid or its p-methoxy derivative, (6) 4-amino-2- N-ethyl - chloropropiontoluidide # (neutral) N-m-methylphenyl-2:8:6-acid, (7) 3-aminochloroacetanilide-4-sulphonic acid # (alkaline) N-p-methoxyphenyl-2:8:6-acid. A table is also given showing the shades obtainable on wool with the dyestuffs from various combinations of components coupled in some cases in presence of acetic acid and in others in presence of sodium carbonate. Specifications 216,971, [Class 2 (iii)], 340,640, 472,171, 544,409 and 553,204 are referred to. 2-p- Carboxyphenyl- 8 - naphthol - 6 - sulphonic acid is obtained by reaction of 2:8:6-aminonaphtholsulphonic acid with p-aminobenzoic acid in presence of sodium bisulphite.