Patent GB-421971-A (GB)
Title: Manufacture of insoluble azo-dyestuffs on the fibre
IPC: D06P3/68
Filed: 1933-06-22
Abstract: Insoluble azo-dyestuffs are made on the fibre by applying a mixture containing an alkali salt of a diazo-sulphonic acid of the general formula <FORM:0421971/IV/1> wherein R=an alkyl, aralkyl or alicyclic radical and wherein the aromatic nuclei may contain substituents, and an alkali salt of an o-coupling hydroxylated component, provided that neither of the dyestuff components contain a group producing solubility in water, and then subjecting the goods thus treated to a steaming operation.  The free coupling component and sufficient alkali may also be used instead of the alkali salt.  Dyeing assistants may be added.  In examples: (1) cotton is printed with a paste containing the sodium salt of 4-benzylamino-2 : 5-dimethoxybenzene-1-diazosulphonic acid, 2 : 3 - oxynaphthoylaminobenzene, caustic soda, thiodiglycol, sodium chromate and starch tragacanth, dried, steamed, rinsed in an acid solution, soaped and rinsed (greenish blue); (2) the potassium salt of 4 - mono - n - butylamino - 3 - chlorobenzene - 1 - diazosulphonic acid and 2 : 3 - oxynaphthoyl - (1 - amino - 2 - methyl - 5 - chlorobenzene) is used as in (1); (3) the sodium salt of 2 : 5 - dimethoxy - 4 - (2<1> : 6<1> - dichlorbenzylamino)-benzene - 1 - diazosulphonic acid and the p-chloranilide of 2 : 3 - oxynaphthoic acid are ground with sodium acetate and then with caustic soda; (4) the sodium salt of 4-methylamino - 3 - chlorobenzene - 1 - diazosulphonic acid, the disodium salt of the o-toluidide of 2 : 3 - oxynaphthoic acid are ground with sodium acetate.  Other components specified are the 2 : 3 - oxynaphthoyl derivatives of o-anisidine and 1-amino-4-methoxy-2-methylbenzene, diacetoacetyl-o-tolidine, 2-hydroxycarbazole - 3 - carboyl - (1 - amino - 4 - chlorbenzene); the diazosulphonate of 1-amino-4-cyclohexylaminobenzene - 3 - sulphonyldiethylamine. The process may be applied to viscose or silk. The Specification as open to inspection under Sect. 91 comprises the use of the following components: b -naphthol and its derivatives e.g. aroylaminonaphthols, arylides of 2 : 3-oxynaphthoic acid (Specification 23732/13, [Class 2 (iii)]), arylides of 6-halogen or 6-arylamino - 2 : 3 - oxynaphthoic acid (Specification 330,349, [Class 2 (iii)]), 1 - naphthol - 4 - carboxylic acid derivatives (Specification 211,223, [Class 2 (iii)]), e.g. 1 - naphthol - 4 - phenylketone, pyrazol nes and b -ketone-aldehyde derivatives (Specifications 211,814 and 211,772, [both in Class 2 (iii)]); dioxyquinolines (Specification 332,940, [Class 2 (iii)]), arylides of 6- or 7-hydroxy - 2 : 1 - and 1 : 2 - naphthocarbazolecarboxylic acids (Specification 330,643, [Class 2 (iii)]) and arylides of 2-oxyanthracene-3-carboxylic acid (Specification 367,907).  In the examples the components of (1) and (2) above are ground with sodium acetate before incorporation into the printing paste.  In a further example the sodium salt of 2 : 5-dimethoxy - 4 - (2<1> : 4<1> - dichlorobenzylamino) - benzene - 1 - diazosulphonic acid, the m-chloranilide of 2 : 3-oxynaphthoic acid, sulphur and sodium sulphite are ground to a powder, made into a paste with caustic soda, thiodiglycol, sodium chromate and starch tragacanth and printed as above.  The following additional components are specified in a table: diazosulphonates of 1 - amino - 4 - benzylamino - 2 - methylbenzene and 1 - amino - 4 - (2<1> : 4<1> - dichlorbenzylamino) - 2 : 5 - dimethoxybenzene; the a  - naphthylamide, the 2 : 5 - dimethoxyanilide, the 2 : 5 - dimethoxy - 4 - bromoanilide, the 4 - methoxy - 3 - methylanilide, the m-nitranilide of 2 : 3-oxynaphthoic acid, 1-phenyl-3-methyl - 5 - pyrazolone, the o - toluidide of 2-oxyanthracene - 3 - carboxylic acid and the 2 : 4 - dimethoxyanilide of 6 - bromo - 2 : 3 - oxynaphthoic acid. This subject-matter does not appear in the Specification as accepted.  1 - Amino - 4 - benzylamino - 2 : 5 - dimethoxybenzene and 1 - amino - 4 - (2<1> : 6<1> - dichlorobenzyl) - amino - 2 p  : 5 - dimethoxybenzene are made by causing benzyl chloride or the appropriate substitution product thereof to react on the appropriate nitroamino compound in presence of sodium acetate and reducing.  1 - Amino - 4 - methyl - or n - butylamino - 3 - chlorobenzene are made by condensing methylamine and n-butylamine respectively with 3 : 4 - dichloronitrobenzene and reducing.  1 - Amino - 4 - cyclohexylaminobenzene - 3 - sulphonyldiethylamine is made by condensing cyclohexylamine with 1-chloro-4-nitrobenzene-2-sulphonic acid, converting into the sulphochloride, condensing with diethylamine and reducing.