Patent GB-740579-A (GB)
Title: Improvements in diazoamino derivatives and the colouration of materials therewith
Inventor: PETITCOLAS PIERRE
Filed: 1953-07-16
Abstract: The invention comprises: diazoamino compounds of the general formula YOOC-A-NX-N=N-R wherein Y represents hydrogen or an alkali metal, A an o-phenylene group which may be unsubstituted or halogen-substituted, X an alkyl, aralkyl or cycloalkyl radical of at least 3 carbon atoms, and R the radical of a diazotizable amine having a dissociation constant not greater than 3.5 X 10-13; the preparation thereof by condensing the diazo compound from an amine RNH2, in a non-acid medium, with an anthranilic acid derivative of the formula YOOC-A-NH-X; mixtures of the diazoamino compounds with at least one coupling component; and the printing of cellulosic fabrics with the aid of such mixtures (see Group IV(c)).  Specified components, some of which are used in the examples, are: amines RNH2: nitranilines, nitrotoluidines (e.g. 4-nitro - 1 - amino - 2 - methylbenzene), nitroanisidines (e.g. 4 - nitro - 1 - amino - 2 - methoxybenzene), nitrocresidines, dichloranilines (e.g. 2:5-dichloraniline), and aromatic bases containing sulphamido, sulphone or trifluoromethyl groups (e.g. 1-methyl-2-amino-4-dimethylsulphamido- and -4-ethylsulphone-benzene, and 1-chloro-3-amino-4-trifluoromethylbenzene); anthranilic acid derivatives: N-propyl-, N-sopropyl-, N-butyl-, N-isobutyl-, N-isoamyl-, N-benzyl- and N-cyclohexyl-anthranilic acid, and 5-chloro-2-N-isopropylaminobenzoic acid.ALSO:Fabrics of natural or regenerated cellulose are printed by applying thereto a printing paste containing at least one coupling component and a diazoamino compound of the general formula: YOOC-A-NX-N=N-R (wherein Y represents hydrogen or an alkali metal, A an o-phenylene group which may be unsubstituted or halogen-substituted, X an alkyl, aralkyl or cycloalkyl radical of at least 3 carbon atoms, and R the radical of a diazotizable amine having a dissociation constant not greater than 3.5 X 1013, and developing the dyestuff in a neutral atmosphere. Specified components (some of which are employed in examples of the printing of cotton using pastes containing caustic soda solution and a thickener of starch-tragacanth or starch ethers, together with thiodiglycol in most cases, denatured alcohol in one case, sodium chlorate in one case and sodium chromate in one case) are: amines RNH2; nitranilines, nitrotoluidines (e.g., 4-nitro-1-amino - 2 - methylbenzene), nitroanisidines (e.g., 4 - nitro-1-amino-2-methoxybenzene), nitrocresidines, dichloranilines (e.g., 2 : 5-dichloraniline), and aromatic bases containing sulphamido, sulphone or trifluoromethyl groups (e.g., 1-methyl-2-amino-4-dimethylsulphamido - and -4-ethylsulphonebenzene, and 1-chloro-3-amino-4-trifluoromethylbenzene); anthranilic acid derivatives YOOC-A-NH-X: N-propyl-, N-isopropyl-, N-butyl-, N-isobutyl-, N-isoamyl-, N-benzyl- and N-cyclohexyl-anthranilic acid, and 5-chloro-2-N-isopropylaminobenzoic acid; coupling components: 2 : 3-hydroxynaphthoic arylides (e.g., the o-toluidide, a -naphthylamide and o-phenetidide), the a -naphthylamide of 5:6:7:8-tetrahydro-2-hydroxynaphthalene-3-carboxylic acid, arylides of other o-hydroxycarboxylic acids (e.g., 2-hydroxy-anthracene-, -carbazole-, benzcarbazole- or -diphenylene-oxide-3-carboxylic acid) or of acylacetic (e.g., acetoacetic, benzoylacetic or terephthaloyl-bis-acetic) acids, and certain hydroxyazo dyestuffs.