Patent GB-555337-A (GB)
Title: New monoazo dyestuffs
IPC: C09B29/30
Filed: 1942-02-11
Abstract: 555,337. Dyes. KNIGHT, A. H., and IMPERIAL CHEMICAL INDUSTRIES, Ltd. Feb. 11, 1942, No. 1788. [Class 2 (iii)] Monoazo dyes, suitable for colouring animal fibres, e.g. wool or silk, and dyeing wool from an acid bath orange and red shades, fast to severe washing and milling, to perspiration 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, but is free from any hydroxy or carboxy group in o-position to the primary amino group, X represents a monochloro-or monobromo-alkyl (C 1  to C 3 ) radicle and Y represents hydrogen, unsulphonated alkyl (C 1  to C 6 ), cycloalkyl, aralkyl, alkoxyalkyl or aryl, and coupling with an N-acyl derivative of 2:5:7- or 2:8:6-aminonaphtholsulphonic acid, wherein the acyl group is of the monohalogenalkyl (C 1  to C 3 )-CO-type and the other amino hydrogen atom may be substituted, if desired, by an alkyl or hydroxy- . alkyl group. Specified diazo components are the 4-amino-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-α chloroacettoluidide, 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 - butylchloroacetanilide - 2 - sulphonic acid, 4 - amino - 1 - N ethyl - bromoacetanilide, 5 - amino - 2 - N - cyclohexyl - chloroacettoluidide, 3 - amino - 1 - N - benzyl - chloroacetanilide, the 4 - amino - N - cyclohexyl derivatives of bromoacetanilide, α- and #-bromopropronanilides and #- chloropropionanilide and 4-amino-l- N - #-ethoxy ethyl-chloroacetanilide. Specified coupling components are the N-chloro- or bromo-acetyl, N-#-chloro- or bromo-propionyl and N-chloroacetyl-N-ethyl-derivatives of 2:5:7-acid and the N-chloro, bromo- or iodo-acetyl, N-#-chloro- or bromo-propionyl, N-chloroacetyl-N-methyl and N-α-bromopropronyl-N-#-hydroxyethyl derivatives of 2:8:6-acid. Examples relate to the production of the dyestuffs, (1) and (2), 4-amino- 1-N-ethyl-chloroacetanilide # (1) N-chloroacetyl-2:5:7-acid, (2) N-chloroacetyl-2:8:6-acid, (3), (4) and (5), 4-amino-2-N-ethyl-chloroacettoluidide# (3) N-chloroacetyl-2:5:7-acid, (4) N- #-chloropropionyl-2:5:7-acid, (5) N-chloroacetyl- 2:8:6-acid, (6) 4-amino-2-N-ethyl-#-bromopropiontoluidide# N-chloroacetyl-2:8:6-acid, (7) and (8), 4-amino-2-N-benzyl-chloroacettoluidide# (7) N-chloroacetyl-2:5:7-acid, (8) N- chloro- or bromo-acetyl-2:8:6-acid, (9) 4-amino- 1- N-isopropyl-chloroacetanilide # N-chloroacetyl-2:5:7-acid; (10)4-amino-l-N-cyclohexylchloroacetanilide# N- #-chloropropionyl-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 216,971, [Class 2 (iii)], 340,640, 341,461, 432,020, 472,171, 544,409 and 553,204 are referred to. NAcyl derivatives of 2:5:7- and 2:8:6-aminonaphtholsulphonic acids as above are obtained by reaction of the sodium salt of the appropriate 2:5:7- or 2:8:6-acid or its N-alkyl or N-hydroxyalkyl derivative with the appropriate halogenacyl chloride in a slightly alkaline aqueous solution at 10-20‹C.