Patent GB-554978-A (GB)
Title: New monazo dyestuffs
IPC: C09B29/30
Filed: 1941-12-22
Abstract: 554,978. Dyes. KNIGHT, A. H., STEPHEN. W. E., and IMPERIAL CHEMICAL INDUSTRIES. Ltd. Dec. 22, 1941, Nos. 16483 and 16601. [Class 2 (iii)] Monoazo dyes, suitable for colouring animalfibres, e.g. wool or silk, and dyeing wool from an acid bath red or red-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<SP>1</SP> to C 3 ) group and Y represents H, unsulphonated alkyl (C 1  to C 6 ), cyclo-alkyl, aralkyl, alkoxyalkyl or aryl, and coupling with an N-acyl-2- amino-8-naphthol-6-sulphonic acid of which the acyl group is of the general formula -CO-M, wherein M represents an aliphatic (C 1  to C 6 ) hydrocarbon radicle and the remaining H atom of the 2-amino group may be replaced by alkyl, hydroxyalkyl or aryl. Specified diazo components are the N-ethyl, N-isopropyl, N-nbutyl, N-sec.-butyl N-cyclohexyl, N-#-ethoxyethyl, N-benzyl and N-phenyl derivatives of 4- amino-chloroacetanilide, the N-ethyl derivatives of 4-amino-#-chloro and bromo-propionanilides, the 2-N-ethyl derivatives of 4-amino-2-N- chloroacettoluidide, 4-amino- 2- N - chloroacetanisidide and 4-amino-2-N-#-chloro- or α- or #- bromo-propiontoluidide, 4-amino-2-N-benzylchloroacettoluidide, 4-amino-N-benzyl-chloroacetanisidide, 2 - amino - 4 - N - ethyl - chloro - acettoluidide, 5 - amino - 2 - N - cyclohexyl - chloroacettoluidide, 4 - amino - N -À ethyl - or cyclohexyl - bromoacetanilide, 3 - amino - X - benzyl - chloroacetanilide, the N - cyclo - hexyl derivatives of 4 - amino - # - chloro - or α - or # - bromo - propionanilide, 3 - amino - N - benzyl - # - chloropropionanilide, 4 - amino - 2 - N - ethyl - α - bromobutyrtoluidide, 3 - amino - chloroacetanilide - 4 - sulphonic acid, 4 - amino - chloroacetanilide - 3 - sulphonic acid and 4-amino-N-n-butyl or cyclohexyl-chloroacetanilide - 2 - sulphonic acid. Specified coupling components are the N-acetyl, N- propionyl, N-n-butyryl, X-isobutyryl, N- methyl - N - acetyl, N - ethyl - N - acetyl, N - # - hydroxyethyl - N - acetyl, N -  # - hydroxypropyl - N - acetyl and N - phenyl - N - acetyl derivatives of 2:8:6 - aminonaphthol - sulphonic acid. Examples relate to the production of the dyestuffs, (1) and (2), 4-amino-N- ethyl - chloroacetanilide - (1) N - acetyl - 2:8 : 6- acid, (2) N-methyl - N - acetyl - 2:8:6 - acid; (3) 4 - amino - N - ethyl - # - chloropropion - anilide # N - acetyl - or N - n - butyryl 2:8:6 - acid, (4) 3 - amino - chloroacetanilide - 4 - sulphonic acid # N - acetyl - 2:8:6 - acid, (5) 4 - amino - 2 - N - ethyl - # - chloro - or α- or #-bromo-propiontoluidide # N-acetyl- 2:8:6 - acid, (6) 4 - amino - N - isopropyl or sec. butyl - chloroacetanilide # N - acetyl - or N - isobutryl - 2:8:6 - acid, (7) 3 - amino - N - - benzyl - chloroacetanilide # N - acetyl - 2:8:6 - acid, (8) to (10), 4 - amino - N - cyclohexyl - chloroacetanilide # (8) N - acetyl- 2:8:6 - acid, (9) N - propionyl - 2:8:6 - acid, (10) N - n - butyryl - 2:8:6 - acid, (11) 4 - amino - N - cyclohexyl - chloroacetanilide # N - methyl - N- acetyl -, N - ethyl - N - acetyl - or N - # - hydroxyethyl - N - acetyl - 2:8:6 - acid, (12) 4 - amino - N - # - ethoxyethyl - chloroacetanilide # N - acetyl - 2:8:6 - acid, (13) 4 - amino - N - cyclohexyl - # - chloro - or α - or # - bromo - propionanilide # N - acetyl -, N - methyl - N - acetyl - or N - - #- hydroxyethyl - N - acetyl - 2:8:6 - acid. A table' is also given showing the shades of the dyeings on wool obtainable with various conbinations of components. 4- Amino- N- cyclohexyl - chloroacetanilide - 2 - sulphonic acid is obtained by reducing the nitro group in the product of chloroacetylation of sodium 4 - nitro - N - cyclohexylaniline - 2 - sulphonate. Specifications 340,640, 424,354, 472,171, 544,409 and 553,204 are referred to.