Patent GB-396893-A (GB)
Title: Process for dyeing or printing textile materials consisting of or containing cellulose esters and cellulose ethers
IPC: C07D231/22
Filed: 1932-05-19
Abstract: Textile materials containing cellulose esters and ethers are dyed, or printed with products obtained by condensing a compound containing a reactive methyl or methylene group with an aromatic aldehyde or nitroso compound, especially one containing a NH2 group unsubstituted, or substituted by alkyl, aryl, &c., or aralkyl. According to examples, acetate silk is dyed with (1) products obtained by condensing p-dimet ylaminobenzaldehyde with 1-(2<1>chloro) phenyl-3-m thyl-5-pyrazolone, ethylcyanacetate, and corresponding methyl, isopropyl and butyl esters, (2) products obtained by saponifying the esters after condensation, and (3) products obtained by condensing p-nitrosodimethylaniline with 1 phenyl-3-methyl-5-pyrazolone.  A table is given showing the colours on cellulose ester materials given by the condensation products from the following compounds, containing reactive methyl groups, and aromatic aldehydes:--(1) p-diethylaminobenzaldehyde and benzyl cyanide, or 1-p-chlorophenyl-3-methyl-5-pyrazolone; (2) p-dimethylaminobenzaldehyde and the following:--benzyl cyanide, p-nitrobenzylcyanide diketohydrindene, nitromethane, malonitrile, dimethylaminobenzalacetone, cyanacetic acid ethyl ester, (followed by conversion to the amide, ethanolamide, diethylamide and monoethylamide), cyanacetic acid anilide, cyanacetic acid monohydrazide, cyanacetic dimethylaminoanilide, 3-methy -5-pyrazolone, 1-(m-aminophenyl) 5-pyrazolone 3-carboxylic acid, 1-phenyl-5-pyrazolone-3-carboxylic ethyl ester, 1-oxynaphthalene acetophenone, methoxyacetophenone, cyanacetophenone, 2 : 4 diketotetrahydrothiazole, barbituric acid, ethyl malonate, ethylacetoacetate, acetoacetanilide, acetoacetic-o-anisidide, acetoacetic p-dimethylaminoanilide, 2 : 4, dioxyquinoline, 6-(2 : 4) dinitro) phenylaminomethylbenzimidazole, methylbenzimidazole, a -methyl-indol, 2 : 3 : 3-trimethylindoleninium methylchloride, 6-methylquinaldine, p-chloro-a -methyl indol, pyruvic ethyl ester, fluorene, and p-xylylene dicyanide; (3) o-chloro-p-dimethylaminobenzaldehyde with nitromethane, and malonitrile; (4) p-aminobenzaldehyde with 1-phenyl-3-methyl-5 pyrazolone, and cyanacetic acid ethyl ester; (5) 2 : 4 diaminobenzaldehyde with N-ethylrhodanine; (6) 3-nitro-4-dimethylaminobenzaldehyde with cyanacetic ester; (7) the product of coupling diazotized p-aminobenzaldehyde and dimethylaniline condensed with cyanacetic ester, and 1-(o-chloro) phenyl 3-methyl-5-pyrazolone, and the product of coupling diazotized p-aminobenzaldehyde and aniline, condensed with 1-(o-chloro-) phenyl-3-methyl-5-pyrazolone.  The following condensations of compounds containing reactive methyl groups, and aromatic nitroso compounds are also referred to:--p-nitrosodimethylaniline with:--benzyl cyanide, p-nitrobenzylcyanide, diketohydrindene, malonitrile, 5-methyloxythionaphthene, 2 : 5 dimethylpyrazine, and 3-methyl-5 - pyrazolone; nitrosodimethylaniline with oxy-thionaphthene and 2 : 3-naphthioindoxyl; oxy-thionaphthene with 2-chloro and 2-oxy-4 dimethylamino-1-nitrosobenzene; and p-nitrosodiethylaniline with dimethylaminobenzalacetone.  Other compounds containing reactive methyl or methylene groups which may be similarly condensed, are sulphazones, quinaldines, acylacetones, and dihydroresorcinols.  6-(2 : 4 Dinitro)-phenylaminomethylbenzimidazole is obtained by reducing acetyl 2 : 4-dinitraniline to 6-aminomethylbenzimidazole and condensing with 2 : 4-dinitrochlorobenzene.