Patent GB-463305-A (GB)
Title: Insoluble azo compounds
IPC: D06P3/68
Filed: 1935-09-20
Abstract: Yellow azo dyes are produced on cellulosic fibres, such as cotton and viscose artificial silk, by printing the material with a composition comprising a water-soluble diazoimino compound of an amine of the formula. <FORM:0463305/IV/1> (R = methyl or ethyl and Hal = chlorine or bromine) and the acetoacetyl derivative of an amine of the formula <FORM:0463305/IV/2> in which (a) X = OCH3 or OC2H5, and of Y and Z, one is H and the other is Cl; or (b) X is H, and of Y and Z one is H and the other is OCH3 or OC2H5; or (c) X and Y both stand for CH3 and Z = Cl, and developing the colour by an acid treatment.  The shades are fast to light and chlorine.  In examples: (1) cotton is printed with a paste comprising the diazoimino compound from diazotized 4-chlor-o-anisidine and piperidine-a -carboxylic acid, acetoacetyl-p-phenetidine, cellosolve (glycol monoethyl ether), caustic soda, wheat starch and gum tragacanth, exposed to acetic acid vapours, rinsed and soaped; (2) 4-chlor-o-phenetidine; and (3) 4-brom-o-anisidine are used instead of 4-chlor-o-anisidine in (1). Sarcosine, ethyltaurine, proline, 4 - sulpho - 2 - aminobenzoic acid and methylglucamine may be used instead of piperidine - a  - carboxylic acid.  Specifications 320,324, 329,353, 334,529, [all in Class 2 (iii)], 422,195, and 429,618 are referred to.  The Specification as open to inspection under Sect. 91 comprises the production of azo dyes in substance or on the fibre from diazoimino compounds of arylamines and acetoacetylamines.  Wool, silk, cellulose esters and ethers are also specified as fibres. Arylamines specified as diazo components are 2-methoxynaphthylamine, 2-methoxy-, phenoxy and ethoxy aniline, 2 - chlor - 5 - methylaniline, 2 - methylaniline, 2 - methoxy - 5 - methylaniline, 2 - methoxy - 4 - chlor-5-methylaniline, 2 : 5-dimethoxyaniline, 2 : 5-diethoxyaniline, 2 : 5-dimethoxy-4-chloraniline, 5-brom-2-methoxyaniline, 3-iodo-6-methoxy or ethoxy-aniline, 3-methyl-4-chloraniline, 3-brom- or chlor-6-ethoxyaniline, 3-ethoxy-, 3-phenoxy- or 3-methoxyaniline, 3-bromo- or iodo-6-phenoxyaniline, 3-bromo- or 3 - chloro - 6 - methylaniline, 3 - methylaniline, 3 - brom - 5 - methylaniline, 3 - chlor-6 - phenoxyaniline, 2 : 5-dimethyl-4-chloraniline, 4-ethylaniline, 4 - benzotrifluoraniline, 4 - chlor - 2 - methoxyaniline, 4 - brom - 2 - methoxy- or ethoxyaniline, 4 - iodo - 2 - methoxyaniline, 4-methoxyaniline, 4-chlor-2-ethoxyaniline, 4-phenoxyaniline, 4-ethoxyaniline, 4 - brom - 2 - phenoxyaniline, 4 - methoxy - 2 - chloraniline, 4 - chlor - 2 - methylaniline, 4 - methyl - 3 - bromaniline, 4 - brom - 3 - methylaniline, 4 - methyl - 3 - chloraniline, 4 - toluidine, 4 - chlor - 2 : 5-dimethylaniline, 4 - chlor - 2 - phenoxyaniline, 4-methoxy-3-chloraniline, 4-phenoxy-2-chloraniline, 4-chlor-2 : 5-diethoxyaniline, 3-ethoxyaniline, 3-methoxyaniline, 3-toluidine, 3-chlor-2-methylaniline, 3-chlor-2-methoxyaniline, 2-ethoxy- or 2-methoxyaniline, o-toluidine, a - and b -naphthylamine.  As coupling components are specified the acetoacetyl derivatives of 2-brom-4-methylaniline, 2-chlor-4-ethylaniline, 2-chlor-4-phenoxy- or 4-ethoxyaniline, 2-ethoxyaniline, 2 - methoxy - 1 - naphthylamine, o - toluidine, 2-methoxy-4-chlor-5-methylaniline, 2-ethoxy-4 - chloraniline, 2 - methoxy - 5 - bromaniline, o-anisidine, 2 - phenoxyaniline, 2 - methoxy - 5 - methylaniline, 2-methoxy-4-chloraniline, 2-methyl-4- or 5-chloraniline, 2-methyl-3-chloraniline, 2-methoxy- or -2-ethoxy-5-chloraniline, 2-methyl-5-bromaniline, 2-methoxy-4-bromaniline, 2-methoxy-3- or 4-methyl-5-chloraniline, o - chloraniline, 2 : 5 - dichlor - 4 - methylaniline, 2 : 5 - dichloraniline, 2 : 5 - dimethoxyaniline, 2 : 5-dimethoxy-4-chloraniline, 2 : 4- or 2 : 5-dimethylaniline, 2 : 5 - diethoxyaniline, 2 : 5-dimethyl - 4 - chloraniline, 3 - chlor - 4 - methylaniline, 3-brom-4-methoxyaniline, 3-brom-4-ethylaniline, 3 - brom - 4 - benzyloxyaniline, 3-chlor-4-methoxyaniline, 3-brom-4-methylaniline, 3-methoxy-1-naphthylamine, 3-brom-1 - naphthylamine, 3 - chlor - 6 - methoxy- or 6-phenoxyaniline, 3-methoxyaniline, 3-chloraniline, 3 - brom - 6 - methylaniline, 3 - ethoxyaniline, 3-methoxy-4-chloraniline, 3-methoxy-4 - bromaniline, 3 - ethoxy - 4 - chloraniline, 3-methoxy - 5 -chloraniline, 3 - methoxy - 5 - bromaniline, 3 - methoxy - 4 - methyl - 6 - chloraniline, 3 - phenoxyaniline, 3 - cyclohexylaniline, 3-benzyloxyaniline, 3 : 5-dimethoxyaniline, 3 : 5-dimethoxy - 4 - chloraniline, 3 : 5 - diethoxyaniline, 3 : 5-dimethylaniline, 4-methoxy-1-naphthylamine, 4-methyl-1- or 2-naphthylamine, 4-ethoxyaniline, 4-methyl-5-chloraniline, 4 - chlor - 6 - methoxyaniline, 4 - methylaniline, 4 - brom - 6 - ethoxyaniline, 4 - methyl - 5 - bromaniline, 4 - phenylaniline, 4 - phenoxyaniline, 4 - methoxyaniline, 4 - chlor - 7 - naphthylamine, 4 - benzyloxyaniline, 5 - methoxy - 1 - naphthylamine, 5-chlor-1- or 7-naphthylamine, 5-chlor-6-methyl- or 6-methoxyaniline, 7-chlor-1-naphthylamine, p-chloraniline, a - or b -naphthylamine.  The dyes in general may be substituted by alkyl, alkoxy, halogen, aryloxy, aralkyl, aralkyloxy, aryl, hydroaryloxy, and trifluoroalkyl groups. Examples of printing as in (1) above with some of the above components are given also with the following; diazo components: 5-chlor-2- or 6-methylaniline, 4-chlor-6-methoxy- or 6-ethoxyaniline; coupling components; the acetoacetyl derivatives of 7-methoxy - 1 - naphthylamine, 3-chlor-6-methylaniline and 2 : 5 - diethoxy - 4 - chloraniline. Pipecolinic acid is also specified as a stabilizer in one example. In a table the following additional components are also specified: diazo components; 5-chlor-6-methylaniline, 3-bromo-6-methoxyaniline, 4 - brom - 5 - methylaniline, 4 - methoxy - 5 - chloraniline, 4 - ethoxy-6 - chloraniline, 4 - chlor - 6 - methylaniline, 3 : 6-dimethyl - 4 - chloraniline, 4 - methyl - 5 - bromaniline; coupling components; the acetoacetyl derivatives of m - toluidine and 6 - chlor - 4-methoxyaniline.  This subject-matter does not appear in the Specification as accepted.