Patent GB-548060-A (GB)
Title: New monoazo red acid dyes
IPC: C09B29/30
Filed: 1941-03-21
Abstract: 548,060. Dyes. KNIGHT, A. H., and IMPERIAL CHEMICAL INDUSTRIES, Ltd. March 21, 1941, Nos. 3858 and 3859. [Class 2 (iii)] Monoazo dyes giving, from an acid or neutral bath, red dyeings, fast to washing, milling, perspiration, sulphur stoving and light, on animal fibres, such as wool and silk, are obtained by coupling a diazotized 4-N-benzoyl-N-cyclohexyl- or methylcyclohexyl-amino-aniline with a 1-N-benzoylamino-8-naphthol-3:6- or 4:6- disulphonic acid, the components being so chosen that the benzoyl groups together carry at least one nuclear chloro or bromo substituent. Specified chloro- and bromo-substituted diazo components are the 2<SP>1</SP>-, 3'- and 41-chloro or bromo, 2:5<SP>1</SP>-dichloro and 2<SP>1</SP>-chloro-5<SP>1</SP>-bromo derivatives of 4:-N-benzoyl-N-cyclohexyl-aminoaniline and the 21-chloro derivative of 4-N- benzoyl-N-p methylcyclohexyl - amino aniline. Specified chloro- and bromosubstituted coupling components are the 2<SP>1</SP>-, 3<SP>1</SP>- and 4<SP>1</SP>- chloro- or bromo-, 2<SP>1</SP>:4<SP>1</SP>- and 2<SP>1</SP>:5<SP>1</SP>-dichloro-, 2<SP>1</SP>-chloro-5<SP>1</SP>-bromo- and 3<SP>1</SP>-chloro-4<SP>1</SP>-bromo-N- benzoyl derivatives of 1:8:3:6- and 1:8:4:6- aminonaphtholdisulphonic acids and 1-(2<SP>1</SP>:5<SP>1</SP>-dibromobenzoyl)amino - 8 - naphthol - 3:6 - disulphonic acid. Examples relate to the production of the dyestuffs, (1), (2) and (3) 4-N-(2<SP>1</SP>:5<SP>1</SP>- dichlorobenzoyl)-N-cyclohexyl-amino-aniline# (1) 1-(21-chlorobenzoyl) amino-8-naphthol-3:6- or 4:6- disulphonic acid or 1-(2<SP>1</SP>:5<SP>1</SP>-dichlorobenzoyl)amino-8-naphthol-3:6-disulphonic acid, (2) 1-(2<SP>1</SP>:5<SP>1</SP>-dichlorobenzoyl)amino-8-naphthol- 4:6-disulphonic acid, and (3) 1-benzoylamino-8- naphthol-4:6-disulphonic acid or its 3<SP>1</SP>-chloro or 3<SP>1</SP>-bromo derivatives ; (4) 4-N-benzoyl-N- cyclohexyl-amino-aniline # 1-(3<SP>1</SP>-bromobenzoyl)amino-8-naphthol-3:6-disulphonic acid ; (5) 4-N- (31-chlorobenzoyl) - N - cyclohexyl - aminoaniline # 1-(3<SP>1</SP>- or 4<SP>1</SP>-bromobenzoyl)amino-8- naphthol-3:6-disulphonic acid; (6) 4-N-(31- or 4<SP>1</SP>-bromobenzoyl)-N-cyclohexyl-amino-aniline # 1-(31-bromobenzoyl)amino-8-naphthol- 3-6-disulphonic acid or 4-N-(4<SP>1</SP>-bromobenzoyl)- N-cyclohexyl-amino-aniline # 1-(3<SP>1</SP>-bromobenzoyl)amino-8-naphthol-4:6-disulphonic acid; (7) 4-N-(2<SP>1</SP>-chlorobenzoyl)-N-cyclohexyl-aminoaniline # 1-(2<SP>1</SP>:5<SP>1</SP>-dichloro- or dibromobenzoyl) amino-8-naphthol-3:6-disulphonic acid ; (8) 4- N - -(4<SP>1</SP> - bromobenzoyl) - N -cyclohexyl - aminoaniline # 1- (2<SP>1</SP>:5<SP>1</SP>- dichlorobenzoyl)amino - 8 - naphthol-3:6-disulphonic acid; (9) 4-N-(31- bromo benzoyl)-N-cyclohexyl-amino-aniline # 1- -(3<SP>1</SP>- chlorobenzoyl)amino - 8 -naphthol- 4:6 - disulphonic acid ; (10) 4-N-benzoyl-N-cyclohexylamino-aniline # 1-(31-chlorobenzoyl)amino-8- naphthol-4:6-disulphonic acid. A table is also given showing the shades obtainable on wool with the dyestuffs from various combinations of components, an additional specified diazo component being 4-N-benzoyl-N-pmethylcyclohexyl-amino-aniline and additional coupling components being 1-N-benzoylamino- 8-naphthol-3:6-disulphonic acid and its 3<SP>1</SP>- chloro and 2<SP>1</SP>:4<SP>1</SP>- dichloro derivatives. Specification 340,640 is referred to. 4-N-Benzoyl-N-cyclohexyl- or methylcyclohexyl-anilines are obtained by reducing the products of reaction of the corresponding 4- nitrocyclohexylaniline or its derivatives (cf. Specification 340,495) with the appropriate benzoyl halide in boiling toluene. 1-N-benzoylamino-8-naphthol-3:6- or 4:6-disulphonic acids, chloro- or bromosubstituted on the benzoyl group, are obtained in the form of their sodium or potassium salts by reaction of the sodium or potassium salt of the 1:8- aminonaphtholdisulphonic acid (1 mol.) in aqueous solution with the appropriate chloro- or bromosubstituted benzoyl halide (1 mol.) in presence of an acid-binding agent such as sodium acetate.