GB595571A - New colouring matters for cellulose esters and ethers and for fibre-forming polyamides and polyesters - Google Patents

Abstract

A dye is prepared by reacting an oxindole, which may carry simple substituents in the benzene ring and in which the -NH- group of the heterocyclic ring is unsubstituted with an aldehyde of formula <FORM:0595571/IV/1> wherein R stands for halogen, CN, COOH or COO.alkyl and in which the phenylene nucleus may carry substituents other than SO3H. The oxindole may be 6-chlorooxindole, 5-bromooxindole, 5-methoxyoxindole, 5-nitrooxindole, 5 : 6-dimethoxyoxindole, 4-carboxyoxindole, or 4 : 5-benzoxindole, and the aldehyde p-(b : b 1-dichlorodiethylamino)-benzaldehyde, p-(b : b 1-dibromodiethylamino)-benzaldehyde, p-(b : b 1-dicyanodiethylamino)-benzaldehyde, p-(b : b 1-dicarboxydiethylamino) - benzaldehyde, or p - (b : b 1 - dichlorodiethylamino) - o - methylbenz - aldehyde. In example (1), a dye is prepared by refluxing together a solution of oxindole and p - (b : b 1 - dichlorodiethylamino) - benzaldehyde in ethanol and piperidine, and adding hydrochloric acid. Examples (2) to (8) describe the similar preparation of dyes from oxindole and p - (b : b 1-dibromodiethylamino)-benzaldehyde, from oxindole and p-(b : b 1-dicyanodiethylamino)-benzaldehyde, from 5-methoxyoxindole and p - (b : b 1-dichlorodiethylamino)-benzaldehyde or p - (b : b 1-dibromodiethylamino)-benzaldehyde, from 4 : 5-benzoxindole and p-(b : b 1-dichlorodiethylamino) - benzaldehyde, from 5-bromooxindole and p - (b : b 1-dichlorodiethylamino) - benzaldehyde or p - (b : b 1 - dibromodiethylamino) - benzaldehyde, from nitrooxindole and p-(b : b 1-dichlorodiethylamino)-benzaldehyde or p-(b : b 1-dichlorodiethylamino)-o-methylbenzaldehyde, and from oxindole and p-(b : b 1-dichlorodiethylamino)-o-methylbenzaldehyde or p-(b : b 1-dichlorodiethylamino)-o-chlorobenzaldehyde. The dyes give fast greenish yellow to orange shades on cellulose esters and ethers and fibre-forming polyamides. p-(b : b 1-Dibromodiethylamino)-benzaldehyde is prepared by reacting N-(b : b 1-dihydroxydiethyl)-aniline in chloroform with phosphorus pentabromide, treating with phosphorus oxychloride and N-methylformanilide, and hydrolysing with aqueous acid. p - (b : b 1-Dicyanodiethylamino) - benzaldehyde is prepared by reacting p-(b : b 1-dibromodiethylamino)-benzaldehyde in aqueous ethanol with sodium cyanide. p-(b : b 1-Dicarboxydiethylamino)-benzaldehyde is prepared by hydrolysing p-(b : b 1-dicyanodiethylamino)-benzaldehyde with caustic soda solution at 90 DEG C. p-(b : b 1-Dichlorodiethylamino)-o-methylbenzaldehyde is prepared from N-(b : b 1-dihydroxydiethyl)-o-toluidine by reacting with phosphorus oxychloride and N-methylformanilide-p-(b : b 1-Dichlorodiethylamino) - o - chlorobenzaldehyde is similarly prepared from N-(b : b 1-dihydroxydiethyl)-o-chloraniline. Specifications 7137/13, [Class 2 (iii)], 456,534 and 458,405 are referred to.