Patent GB-729156-A (GB)
Title: Improvements in colouring compositions and the printing of cellulosic textile materials therewith
Inventor: PETITCOLAS PIERRE
Filed: 1952-09-15
Abstract: Insoluble azo dyes are formed on natural or regenerated cellulose textile materials by applying a printing paste containing at least one coupling component and a diazoamino derivative of the formula <FORM:0729156/IV (c)/1> in which the benzene nucleus A may be substituted by one or more halogen atoms or one or more alkyl or alkoxy groups, R is the radical of an aromatic amine, or the radical of an amine behaving to diazotization like an aromatic amine, and having a more strongly basic character than 2 : 5-dichloraniline, X is a substituted or unsubstituted alkyl or cycloalkyl radical, Y is hydrogen or an alkali metal and n is 1 or 2, and then developing the dyestuff in neutral steam, the use of acid steam being unnecessary. In the formula R may represent the radical of one of the following amines: o-chloraniline, m-chloraniline, 4-chloro-2-amino-1 - methylbenzene, 5 - chloro - 2 - amino - 1-methylbenzene, 4 - chloro - 2 - amino - 1-methoxy - benzene, monobenzoyl paraphenylene-diamines substituted in the 2 : 5-positions by halogen atoms or by -CH3, -OCH3 or -OC2H5 groups, and aminoazotoluene.  The radical X may be any of the following (in which Y is H or alkali metal): -CH2COOY, -CH2. CH2OH, -CH2-CHOH-CH2SO3Y, -CH2 CH2COOY, -CH2CHOHCH2OH, cyclohexyl, -n-C4H9, -CH3, -C2H5, -CH2 CH2OCH3, -CH2CH2OC2H5, -CH2COOCH3, -CH2COOC2H5 and -CH2CONH2. Specified coupling components are 2 : 3-hydroxynaphthoic acid, 2 : 3 - hydroxy - anthracenecarboxylic acid, 2 : 3 - hydroxycarbazolecarboxylic acid, 2 : 3 - hydroxy - benzocarbazole - carboxylic acid, 2 : 3 - hydroxy - diphenylene - oxide - carboxylic acid, acetylacetic -, benzoylacetic - and terephthaloyl bis-acetic acids and hydroxy - azo - dyestuffs derived from 1-amino-7-naphthol.  Numerous examples are given in which the printing pastes contain starch-tragacanth thickener and the following additional ingredients, although not in association: alcohol, sodium sulphoricinoleate, sodium benzene sulphonate, monoethanolamine and copper sulphate.  Specifications 729,157 and 729,158, [both in Group IV (b)], are referred to.ALSO:Mention is made of diazoamino compounds of the formula <FORM:0729156/IV (b)/1> in which the benzene nucleus A may be substituted by one or more halogen atoms or one or more alkyl or alkoxy groups, R is a radical of an aromatic amine, or the radical of an amine behaving to diazotization like an aromatic amine, and having a more strongly basic character than 2 : 5-dichloraniline, X is a substituted or unsubstituted alkyl or cycloalkyl radical, Y is hydrogen or an alkali metal and n is 1 or 2.  The compounds may be prepared from diazo or tetrazo derivatives of mono- or di-amines and N-substituted derivatives of anthranilic acid as described in Specification 729,157 and may be isolated as described in Specification 729,158.  In examples the following preparations are given: (7) from diazotized o-chloroaniline and 5-chloro-2-hydroxyethyl-amino-benzoic acid; (8) from diazotized 1-amino - 4 - benzoylamino - 2 - methoxy - 5 - methyl - benzene and 5 - chloro - 2 - hydroxyethyl-amino-benzoic acid; (9) from diazotized 6-chloro-1-amino-4-benzoylamino-3-methoxybenzene and 5 - chloro - 2 - hydroxyethylamino-benzoic acid; (11) from tetrazotized dianisidine and 5 - chloro - 2 - hydroxyethylamino - benzoic acid; (12) from diazotized 4-chloro-2-amino-1-methoxybenzene and 5-chloro-2-hydroxyethylamino-benzoic acid; (13) from diazotized 4-chloro - 2 - amino - 1 - methylbenzene and N - (2 - carboxy - 4 - chlorophenyl) - glycine; (14) from diazotized m-chloraniline and N-(2-carboxy-4-chlorophenyl)-glycine; (15) from diazotized 6-amino-3-benzoylamino-1-methoxy-4-methylbenzene and N-(2-carboxy-4 : 6-dichlorophenyl)-glycine; (16) from diazotized 4-amino-1-benzoylamino-2 : 5-diethoxybenzene and N-(2-carboxy - 4 - methoxyphenyl) - glycine; (19) from diazotized p-toluidine and the disodium salt of N-(21-hydroxy-31-sulphopropyl) -2-amino-5-chloro-benzoic acid; and (21) from diazotized 4-chloro-2-amino-1-methoxybenzene and N-21 - carboxy - 41 - chlorophenyl) - b  - amino - propionic acid.  5 - Chloro - 2 - hydroxyethylamino - benzoic acid (example 7) is prepared from monoethanolamine and 2 : 5-dichlorobenzoic acid.  N -(2 - Carboxy - 4 - methoxyphenyl) - glycine (example 16) is prepared from 2-amino-5-methoxy-benzoic acid and monochloracetic acid.  N - (21 - Hydroxy - 31 - sulphopropyl) - 2 - amino-5-chloro-benzoic acid (example 19) is prepared from 5-chloro-2-amino-benzoic acid and 1 - chloro - 2 - hydroxy - propane - 3 - sulphonic acid.