Water-insoluble mono-azo dyestuffs

• Main Authors: PETERSEN SIEGFRIED, MITROWSKY ALEXANDER
• Format: Patent
• Language: English
• Published: 03.04.1957
• Subjects: ADHESIVES; CHEMISTRY; DYES; LAKES; METALLURGY; MISCELLANEOUS APPLICATIONS OF MATERIALS; MISCELLANEOUS COMPOSITIONS; MORDANTS; NATURAL RESINS; ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES; PAINTS; POLISHES

N - (2 - nitro - 1 - phenylethyl) anilines are made by treating a nitromethane with a benzalaniline or an aniline with an o -nitrostyrene. The products are dyestuff intermediates, vide Group IV (c). Anilines specified or obtained in examples are N-(2-nitro-1-phenyl- and -m- and -p-nitro- and -chlorophenylethyl) anilines, N-(2 - nitro - 1 - p - chloro - phenylethyl) - m - chloraniline and N - (2 - nitro - 2 - chloro - and -methyl-1-phenylethyl) anilines.ALSO:The invention comprises dyestuffs of formula <FORM:0771566/IV(b)/1> where R is a benzene or heterocyclic residue, Ar is of the benzene series, R1 is H, halogen or alkyl, and Ar and B may carry substituents other than sulphonic and carboxylic acid groups. They are made by coupling appropriate diazotised amines and N - (2 - nitro - 1 - Ar - ethyl) - anilines or derivatives thereof, preferably in an organic acid solution such as formic or acetic acid. Substituents indicated for Ar and B are alkyl, halogen, nitro, mono and dialkylamino, alkylsulphone and alkoxy groups. Addition products of nitromethane and Schiffs' bases also provide starting material. Specified amines for diazotisation are aniline, chloroanilines, toluidines, anisidines, cresidines, nitranilines, chloronitranilines, aminodiphenyl, aminotriazoles and dehydrothiotoluidines. The dyestuffs are orange or red powders and may be used to colour lacquers and waxes and as dispersed dyestuffs for colouring fibres of cellulose acetate and polyamides and polyurethanes. In examples which illustrate the preparation of the dyestuffs and their use in dyeing processes diazo compounds are obtained from 1 - amino - 4 - nitro - and - chloro -, - 2 - chloro - 4 -nitro -, - 2 - nitro - 4 - chloro - and - 2 - methoxy - and - methyl - 4 - nitro - benzenes, p - amino - aceto - and - benzo - phenones and 2 - amino - 6 - methoxy - benzthiazole the coupling components being N - (2 - nitro - 1 - phenyl - and - m - and p - nitro - and - chloro - phenyl - ethyl) anilines, N - (2 - nitro - 1 - p chlorophenylethyl) - m chloraniline and N - (2 - nitro - 2 - chloro - and - methyl - 1 - phenylethyl) anilines.