Patent GB-558058-A (GB)
Title: New monoazo dyestuffs
IPC: C09B29/30
Filed: 1942-06-15
Abstract: 558,058. Dyes. KNIGHT, A. H., STEPHEN W. E., and IMPERIAL CHEMICAL INDUSTRIES, Ltd. June 15, 1942, No. 8141. [Class 2 (iii)] Monoazo dyes are obtained by diazotizing an amine of the formula X-CO-NY-R-NH  2 , wherein X represents a monochloro- or monobromoalkyl radicle having not more than 3 carbon atoms, R represents an m- or p-phenylene residue which may be substituted, e.g., by methyl, methoxy or sulphonic acid groups, but is devoid of nitro groups, Y represents hydrogen, alkyl (C 1  to C 6 ), aralkyl, cycloalkyl, alkoxyalkyl or aryl, and coupling in a neutral or alkaline medium with 2:8:6-aminonaphtholsulphonic acid or a derivative thereof N-substituted by alkyl, cycloalkyl, aralkyl or hydroxyalkyl. The products are applicable for dyeing animal fibres, e.g. wool or silk, and dye wool from an acid bath brown shades, fast to severe washing, to milling and to light. Specified diazo components are the 4-amino-1-N- ethyl, isopropyl, n-butyl, sec.-butyl, benzyl, cyclohexyl and phenyl derivatives of chloroacetanilide, the 4-amino-N-ethyl and benzyl derivatives of 2-chloroacettoluidide, the 4- amino-N-ethyl derivatives of 2-α- and #- bromopropiontoluidides, 3-amino-chloroacetanilide-4-sulphonic acid, 2-amino-4-N-ethylchloroacettoluidide, 4 - amino - 2 - N - ethyl - α - bromobutyltoluidine, 4 - amino - 2 - N - ethyl- # - - chloropropiontoluidide, 4 - amino - 1 - N- ethyl - # - chloro - or bromo - propionanilide, 4 - amino - chloroacetanilide - 3 - sulphonic acid, the 4-amino-1-N-ethyl- and benzyl-derivatives of 2-chloroacetanisidide, 4-amino-1-N-n-butyl- or cyclohexyl chloroacetanilide - 2 - sulphonic acid, 4-amino-1-N-ethyl-bromoacetanilide, 5- amino - 2-N - cyclohexyl - chloroacettoluidide, 3- amino - 1 - N - benzyl - chloroacetanilide, the 4 - amino - 1 - N - cyclohexyl derivatives of bromoacetanilide and α- and #-bromo- and #- chloro-propionanilides, 3-amino-1-N-benzyl- # - chloropropionanilide, and 4-amino-1-N-#- ethoxyethyl - chloroacetanilide. Specified coupling components are 2:8:6-aminonaphtholsulphonic acid and its N-methyl, N-ethyl, N-dimethyl, N-diethyl, N-ethyl-N-#-hydroxyethyl, N-#-hydroxyethyl, N-di-(#-hydroxyethyl), N-cyclohexyl and N-benzyl derivatives. Examples relate to the production of the dyestuffs, (1) and (2), 4-amino-1-N-ethylchloroacetanilide# (1) 2:8:6-acid, (2) N-methyl- 2:8:6-acid, (3) 4-amino-1-N-cyclohexyl-chloroacetanilide# N-methyl- or ethyl-2:8:6-acid, (4) 4- amino-1-N-cyclohexyl-#-chloropropionanilide# N-cyclohexyl-2:8:6-acid, (5) and (6), 4-amino- 1-N-ethyl-#-chloropropionanilide # (5) N- ethyl-2:8:6-acid, (6) N-methyl-2:8:6- acid, (7) 4-amino - 2 - N - ethyl - chloroacettoluidide# N-cyclohexyl-2:8:6-acid, (8) 4-amino-1-N-isopropyl - chloroacetanilide# N-di-(#-hydroxyethyl)-2:8:6-acid, (9) 4-amino-1-N-ethylchloropropionanilide # N-benzyl - 2:8:6-acid. A table is also given showing the shades obtainable on wool with the dyestuffs from various combinations of components. Specifications 340,640, 472,171, 544,409 and 553,204 are referred to. The N-cyclohexyl and N-benzyl derivatives of 2:8:6-aminonaphtholsulphonic acid are obtained by reaction of 2:8:6-acid with cyclohexylamine and benzylamine respectively in presence of aqueous sodium bisulphite. The N-ethyl-N-#-hydroxyethyl derivative of 2:8:6-aminonaphtholsulphonic acid is obtained by reaction of N-ethyl-2:8:6-acid with ethylene chlorohydrin in an aqueous medium in presence of chalk. The N-di-(#-hydroxyethyl) derivative of 2:8:6- aminonaphtholsulphonic acid is obtained by similar reaction of 2:8:6-acid with ethylene chlorohydrin (2 mols.).