Patent GB-554600-A (GB)
Title: New monoazo dyestuffs
IPC: C09B29/30
Filed: 1941-10-08
Abstract: 554,600. Dyes. KNIGHT, A. H., STEPHEN, W. E., and IMPERIAL CHEMICAL INDUSTRIES Ltd. Oct. 8, 1941, Nos. 12979 and 12980. [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 monobromo-alkyl radicle having not more than 3 carbon atoms, R represents a benzene residue, which may be substituted, Y represents hydrogen, unsulphonated alkyl (C 1  to C 6 ), aralkyl, cycloalkyl, alkoxyalkyl or aryl, the NY group being in m- or pposition to the primary amino group, and coupling with an N - acyl - 2:5:7-aminonaphtholsulphonic acid, in which the acyl group is of the type -CO-M, wherein M represents an aliphatic hydrocarbon radicle with not more than 6 carbon atoms, and the coupling component may be further N-substituted by alkyl or aryl. 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 - ethyl - chloracettoluidide, 4 - amino - 2 - N - ethyl - α - bromobutyryl - toluidine, 4 - amino - 2 - N - ethyl - # - chloropropiontoluidide, 4 - amino - 1 - N - ethyl - # - chloro- or bromo-propionanilide, 4 - amino - chloroacetanilide - 3 - sulphonic acid, the 4 - amino - N - ethyl and benzyl derivatives of 2 - chloroacetanisidide. 4 - amino - 1 - N - n - butyl 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, α - and # - bromo- and # - - chloropropionanilides, and 4 - amino - 1 - N - # - ethoxyethyl - chloroacetanilide. Specified coupling components are N - acetyl, propionyl or butyryl, N - methyl - acetyl, N - ethyl - acetyl and N - phenyl - acetyl derivatives of the 2:5:7-acid. The products are applicable for producing orange dyeings on animal fibres, e.g. wool and silk; the dyeings on wool from an acid bath being very fast to severe washing and milling and fast to light. Examples relate to the production of the dyestuffs, (1) 4 - amino - 1 - N - ethyl - chloroacetanilide # N - acetyl - 2:5:7 - acid ; (2) 4 - amino - 2 - N - ethyl - chloroacettoluidide # N - acetyl - 2:5:7 - acid ; (3) 4 - amino - 1 - N - 7 isopropyl - chloroacetanilide # N - acetyl - 2:5:7 - acid.; (4) 4 - amino - 2 - N - ethyl - chloroacettoluidide # N - propionyl - 2:5:7-acid ; (5) 4 - amino - 1 - N- n - butyl - chloroacetanilide # N - acetyl - 2:5:7- acid, (6) 4 - amino - 1 - N - ethyl - # - chloro- or bromo-propionanilide # N - acetyl - 2:5:7 - acid; (7) 4 - amino - 2 - N - ethyl - # - chloropropiontoluidide # N - acetyl - 2:5:7 - acid ; (8) 4 - amino - 2 - N - benzyl - chloroacettoluidide # N - acetyl - 2:5:7-acid ; (9) 3 - amino - 1 - N - benzyl - chloroacetanilide # N - acetyl - 2:5:7 - acid ; (10) 4 - amino - 1 - N - cyclohexyl - chloroacetanilide # N - acetyl -, propionyl - or n - butyryl - 2:5:7- acid ; (11) 4 - amino - 1 - N- cyclohexy 1 - # - chloro- or bromo - or α -bromopropionanilide # N - acetyl - 2:5:7 - acid; (12) 4 - amino 1 - N - # - ethoxyethyl - chloroacetanilide # N - acetyl - 2:5:7 - acid : (13). 4 - amino - 1 - N - phenyl - chloroacetanilide # N - acetyl - 2:5:7-acid. A table is also given showing the shades obtainable on wool with the dyestuffs from various other combinations of components. Specifications 424,354, 472,171, 544,409 and 553,204 are referred to. 4 - Amino - 1 - N - # - ethoxyethyl - chloracetanilide is obtained by reduction of the nitro group in the product of reaction of chloroacetyl chloride with 4 - nitro - 1 - N - # ethoxyethylaniline, which is obtained by hydrolysis of the product of nitration of N - acetylated - N - # - ethoxyethylaniline. N - Propionyl- and N - n - butyryl - 2:5:7 - acid are obtained by reaction of propionic and n - butyric anhydrides respectively with the sodium salt of 2:5:7 - aminonaphtholsulphonic acid in aqueous solution. N - Ethyl - N - acetyl - 2:5:7 - acid is obtained by reaction of acetic anhydride with the sodium salt of N - ethyl - 2:5:7 - aminonaphtholsulphonic acid in aqueous solution.