Patent GB-551435-A (GB)
Title: Improvements in the production of coloured textile and other materials
IPC: C09B69/00
Filed: 1941-07-25
Abstract: 551,435. Coloured fibres. OLPIN, H. C., STANLEY, E., and ARGYLE, C. S. July 25, 1941, No. 9444. [Classes 2 (ii), 2 (iii) and 15 (ii)] Fibres of materials soluble in organic liquids, e.g. cellulose esters or ethers or vinyl polymerisation products, are coloured with a dyestuff carrying a monovalent aliphatic radicle which is free from sulphonic or carboxylic groups and contains at least 8 carbon atoms united by carbon to carbon linkages. The dyestuff may be incorporated by solution or dispersion in the solution from which the fibres are formed or a solution of the dyestuff in an organic liquid may be applied to the fibres (c.f. Specification 550,659). Specified aliphatic radicles are octyl, dodecyl, hexadecyl, octodecyl and octodecenyl. The said aliphatic radicle mav be united to an aryl nucleus of the dyestuff molecule directly or through an atom of O or S or a group -NR 1 -, -CO.NR 1 -, -CO.O-, - CO- or -SO  2 NR 1 -, wherein R, represents H or an organic substituent. Specified azo dyestuffs are 4-stearoylamino - 4<SP>1</SP> - dimethylamino - azobenzene, 4 - dodecyloxy - 4<SP>1</SP> - diethylamino - azobenzene, 4 - nitro - 4<SP>1</SP> - diethylamino - 2<SP>1</SP> - stearoylamino - azobenzene, 4 - stearoylamino - 2<SP>1</SP> - hydroxy - 5<SP>1</SP> - phenyl - azobenzene, 4 - (p - nitrobenzeneazo) - 2:5 - dimethoxy - 4<SP>1</SP> - diethylamino - 2' - stearoylamino - azobenzene, 4 - (p - nitrobenzeneazo) - 5 - acetylamino - 2 - methoxy - 4<SP>1</SP> - diethyl - amino - 2<SP>1</SP> - stearoylamino - azobenzene, 4 - octodecyl - 4<SP>1</SP> - diethylamino - azobenzene, 4 - octodecylaniline # 1 - phenyl - 3 - methyl - 5 - pyoazolone, the dodecyl ester of 4<SP>1</SP>- diethylamino - azobenzene - 4 - carboxylic acid, 2 - aminobenzthiazole # 3 - stearoylamino - N:N - diethylaniline, 4 - dodecylaniline # 1 - (2<SP>1</SP>:5<SP>1</SP> - dichloro - 4<SP>1</SP> - sulpho) phenyl - 3 - methyl - 5 - pyroazolone, 6 - methyl - or methoxy - 2 - aminobenzthiazole # cresidine - 3 - stearoylamino - N:N - diethylaniline and, according to the Provisional Specification, 4 - (p - nitrobenzeneazo) - 2 - acetylamino - 5 - methoxy - 4<SP>1</SP> - diethylamino - 2<SP>1</SP> - stearoylamino - azobenzene. Specified anthraquinone dyes are the 1 - stearoylamino - 4 - anilino, 1 - stearoylamino - 4 - o - anisidino, 1 - amino - 4 - (p - dodecylanilino), 1 - amino - 4 - (p-dodecylmercaptoanilino), 1 - amino - 4 - anilino 2 - dodecyloxy, 1 - amino - 4 - anilino - 2 - dodecylmercapto, 1 - amino - 4 - anilino - 2 - carboxylic acid dodecylamide and 1-amino-4-(p-dodecylanilino)-2-sulphonic acid derivatives of anthraquinone. Specified nitrodiarylamine dyes are 2-nitro - 4<SP>1</SP> - octodecyl - diphenylamine and its 4 - chloro derivative, 2:4 - dinitro - 4<SP>1</SP> - octodecyl - diphenylamine, and 4 - chloro - 2 - nitro - 4<SP>1</SP> - dodecyl - diphenylamine. The coloured materials produced may be tapped with other dyes applied in aqueous'solution or dispersion or in solution in organic solvents, e.g. as described in Specifications 282,036, 313,451, [both in Class 15 (ii)], and 460,575. In examples, (1) 4-nitro-4<SP>1</SP>-diethylamino-2<SP>1</SP>- stearoylamino - azobenzene is incorporated in an acetone solution of cellulose acetate and the solution is dry spun into yarn ; the colour is fast to light and very resistant to removal by hot soap solutions ; (2), (3) and (4), the dyestuff in (1) is replaced by (2) 4-(p-nitrobenzeneazo)- 2:5 - dimethoxy - 4<SP>1</SP> - diethylamino - 21 - stearoylamino - azobenzene, (3) 1 - stearoylamino - 4 - anilino - anthraquinone, (4) 2:4 - dinitro - 4<SP>1</SP> - octodecyl - diphenylamine ; (5) a coloured yarn obtained as in (1) is topped with 1:4-di-(methylamino)-anthraquinone applied from an aqueous dispersion obtained by use of soap, xylene and turkey red oil. Specifications 501,806. 523,287, 550,839, 550,840, 551,434, and 551,437 also are referred to. 1 - Amino - 4 - (p - - dodecylanilino) - anthraquinone and its 2-sulphonic acid are obtained by reaction of p-dodecylaniline with 1-amino-4- bromoanthraquinone and its 2-sulphonic acid respectively. 3 - Steatroylamino - N:N- diethylaniline is obtained by reaction of stearic acid chloride with 3-amino-N:N-diethylaniline. Nitro dyes as above are obtained by reaction of the appropriate halogenaryl compound with the appropriate aminoaryl compound.