Patent GB-551437-A (GB)
Title: Improvements in the manufacture of dyes
IPC: C09B31/043
Filed: 1941-07-25
Abstract: 551,437. Dyes ; artificial silk; cellulose derivative compositions. OLPIN, H. C., STANLEY, E., and ARGYLE, C. S. July 25, 1941. No. 7866/42. Divided out of 551,435. [Classes 2 (ii), and 2 (iii)] Disazo and polyazo dyes, suitable for colouring solutions in organic liquids of film-forming materials, e.g. cellulose ester or ether spinning solutions (cf. Specification 551,435) are obtained by coupling a diazotized aminoazo compound or a tetrazotized diaminoazo compound with a 3 - acidylamino - N - substituted aniline coupling in 4 - position, wherein the acidyl group is that of an aliphatic carboxylic acid containing at least 9 carbon atoms. Specified aminoazo and diaminoazo compounds are those obtainable by coupling diazotized aniline, toluidines, anisidines, phenetidines, 1 - naphthylamine, 2-, 3- or 4-nitroaniline, 2 - chloro - 4 - nitroaniline or 4 - chloro - 3 - nitroaniline with m - toluidine, cresidine, p - xylidine, 2 : 5 - dimethoxyaniline, 2 : 5 - diethoxyaniline, 3 - acetylaminoaniline, 4 - acetylamino - 2 - aminotoluene, 4 - acetylamino - 2 - aminoanisole, 4 - acetylamino - 2 - amino - # hydroxy - ethoxybenzene, 3 - benzoylaminoaniline or 3 - acetylmethylaminoaniline and specifically 4 - aminoazobenzene and its 4<SP>1</SP> - sulpho derivative, 4<SP>1</SP> - chloro - 2 - acetylamino - 4 - amino - 5 - methoxyazobenzene and its 3<SP>1</SP> - nitro derivative, 4 - nitro - 4<SP>1</SP> - aminoazobenzene and its 2<SP>1</SP> - methyl, 2<SP>1</SP>: 5<SP>1</SP> - dimethoxy, 2<SP>1</SP> : 5<SP>1</SP> - diethoxy, 2 - chloro - 21 - methyl - 5<SP>1</SP> - methoxy, 2<SP>1</SP> - acetylamino - 5<SP>1</SP> - methoxy and 2 - chloro - 21 : 51 - dimethoxy derivatives 4 - nitrobenzene - azo - α - naphthylamine and its 2 - chloro derivative, 4 - amino - 2 - acetylamino - 5 - methoxy - 1 : 1<SP>1</SP>-benzeneazonaphthalene, 4 : 4<SP>1</SP> - diamino - 2<SP>1</SP> - acetylamino - 5 - methoxy - azobenzene, and 4 - (benzeneazo)- 41 - amino - 21 : 51 - dimethyl - azobenzene. The acidyl groups in the coupling component may be those of lauric, palmitic, stearic or oleic acid and specified coupling components are the 3 - stearoylamino and 3 - lauroylamino derivatives of N - dimethyl, N - diethyl- and N - di - (# - hydroxyethyl) - aniline and the 3 - stearoylamino derivatives of 6 - methyl - and 6 - methoxy - N - diethyl - aniline. Examples relate to the production of the dyestuffs, (1) 4 - nitroaniline # 2 : 5 - dimethoxyaniline # 3 - stearoylamino - N - diethylaniline, (2) 4 - aminoazobenzene # 3 - stearoylamino - N - diethylaniline. Specifications 523,287, 550,839 and 550,840 also are referred to. The 3 - - Stearoylamino - or lauroylamino derivatives of N - dimethyl- and N - diethylaniline and the 3 - stearoylamino derivatives of 6 - - methyL- and 6-methoxy-N-diethyl - aniline are obtained by the action of stearic or lauric acid chloride on the appropriate 3 - aminoaniline derivative.. The 3 - - Stearoylamino or lauroylamino derivatives of N - di - (# - hydroxyethyl) - aniline are obtained by the action of ethylene chlorohydrin on the N-monostearoyl and N - monolauroyl derivatives respectively of 1 : 3 diamonobenzene.