Patent GB-429618-A (GB)
Title: Manufacture of new diazoimino compounds and their application in dyeing and printing
Filed: 1933-12-04
Abstract: Diazoimino compounds are made by coupling a diazotized aromatic amine, free from water-solubilizing groups, with a secondary sugar amine of the formula, R.NHCH2.(CH.OH)n.CH2OH in which R is an alkyl, aralkyl or alicyclic group free from sulphonic and carboxylic acid groups, and n = 2, 3 or 4.  In examples diazoimino compounds from the following components are described: (1)--(4) m-chloraniline and methyl- or ethyl-glucamine, methylgalactamine or methylxylamine (from xylose); (5) and (6) p-chlor-o-toluidine and methylglucamine or cyclohexylglucamine; (7) 4 - chlor - 2 - aminoanisole and methylglucamine; (8) and (9) p-chloro-o-anisidine and butylxylamine or amylglucamine; (10) and (11) 5-nitro-2-aminoanisole and methylglucamine or benzylglucamine.  Bisdiazoimino compounds can be similarly prepared from tetrazo compounds.  Azo dyes, forming on the material.--Textile materials are coloured by applying to the material a diazoimino compound of the above type and a suitable coupling component singly or in admixture and developing the colour by an acid hydrolysis of the diazoimino compound.  In examples: (12) a paste containing the diazoimino compound from diazotized m-chloraniline and methylglucamine and the o-toluidide of 2 : 3 - oxynaphthoic acid is printed on cotton, the material dried and steamed and the colour developed in a bath containing acetic acid, formic acid and Glauber's salt; (13) the diazoimino compound from m-chloraniline and methylgalactamine is used instead of the diazoimino compound in (12); (14) cotton is printed with a paste containing the diazoimino compound from 4-chlor-2-aminoanisole and methylglucamine and the o-anisidide of 2 : 3-oxynaphthoic acid and the colour developed with steam containing acetic acid vapours; (15) the diazoimino compound from 4-chloro-2-aminoanisole and N-n-butylglucamine is used in place of the diazoimino compound in (14).  In examples (16--(20) pastes containing the following pairs of components are similarly employed: the diazoimino compound from p-chloro-o-anisidine and butylxylamine and the o-anisidide of 2 : 3-oxynaphthoic acid; the diazoimino compound from p-chloro-o-toluidine and methylglucamine and the o-phenetidide or o-toluidide of 2 : 3-oxynaphthoic acid; the diazoimino compound from 4-chloro-2-toluidine and methylxylamine and the o-toluidide of 2 : 3-oxynaphthoic acid; (21) cotton impregnated with the anilide of 2 : 3-oxynaphthoic acid is developed in a bath containing the diazoimino compound from m-chloraniline and ethylglucamine, acetic and formic acids and Glauber's salt; (22) cotton impregnated with the o-toluidide of 2 : 3-oxynaphthoic acid is printed with a paste containing the diazoimino compound of (1), steamed and developed as in (12). Other coupling components specified are arylamides of 2-hydroxycarbazole-3-carboxylic acid, 7 - hydroxy - a  - naphthocarbazole - 6 - carboxylic acid or 2 - oxyanthracene - 3 - carboxylic acid, a - or b -naphthol, acetoacetyl amines and 1-phenyl-3-methyl-5-pyrazolone.  In general diazoimino compounds from amines of the benzene, diphenyl, diphenylamine, naphthalene, azobenzene, anthraquinone, and carbazole series may be used, e.g. 2 : 5-dichloraniline, 5 - nitro - o - toluidine, 4 - amino - 6 - benzoylamino - m - xylene, N - p - aminobenzoyl - p - toluidine, a -aminoanthraquinone, 4 : 4<1> - diaminodiphenylamine a  - naphthylamine 4 - aminoazobenzene 4 - amino, 5-methoxy - 2<1> - ethoxy - 2 - methylazobenzene, 5 - chloro - o - toluidine, 4 - chloro - 2 - nitroaniline, 3-amino carbazole, tolidine, 1 - amino - 4 - benzoylamino - 2 : 5 - diethoxybenzene, o - chloraniline, 4 - chlor - 5 - nitro - o - anisidine.  Sugar omines from the following compounds may also be used in the manufacture of the above diazoimino compounds: glucose, mannose, galactose, xylose, arabinose, erythrose, or other hexoses, pentoses, or tetroses, in d-, l-, meso- or racemic forms and primary amines, e.g. methyl- and ethylamine, n- and iso-propylamines, butylamines, amyl amines, benzylamine, b  - phenylethylamine, a  - naphthylmethylamine, cyclopentylamine, cyclohexylamine, 3 - methylcyclohexylamine.  They may be prepared by reducing a mixture of the sugar and primary amine.