Patent GB-396412-A (GB)
Title: Improvements in the manufacture of azo dyestuffs and in the colouration of textile materials
IPC: C09B29/00
Filed: 1931-10-26
Abstract: Azo dyes are made in substance by coupling any component with a diazo compound obtainable by diazotizing an anthraquinone compound containing an external diazotizable amino group.  The external amino group may be attached to the anthraquinone nucleus in various ways, e.g. the amino group may be present in the aryl residues of arylamino-, aracylamino- or aryloxyanthraquinones. Diazo components specified are aminoaryl- or aminoaracyl derivatives of 1-amino- or 1 : 5- or 1 : 8-diaminoanthraquinone e.g. 1 : 5-di-(p-aminophenylamino)-anthraquinone or 1-(p-aminophenylamino)-anthraquinone or 1-amino-5-(p-aminophenylamino)-anthraquinone; 1-oxy-, 1-amino-, or 1-aliphatically-substituted-amino-4-arylamino-anthraquinones containing an amino group in the aryl residue e.g. 1-amino-, 1-methylamino-, 1-dimethylamino-, 1-(oxyalkylamino)-4-(aminoarylamino)-anthraquinone.  Any desired coupling component may be used, e.g. amines or phenols, pyrazolones and b -ketonic acid derivatives, amides and substituted amides of hydroxy-carboxylic acids e.g. salicylic acid, 2 : 3 or 1 : 4-oxynaphthoic acid, di-2 : 3-oxynaphthoyl dianisidine, diacetoacetyl-o-tolidine.  Coupling components of relatively low molecular weight e.g. phenol, o- or m-cresol, m-phenylenediamine, m-aminophenol, dimethylaniline, m-oxydiphenylamine, 1-phenyl-3-methyl-5-pyrazolone give dyes suitable for cellulose esters and ethers.  Blue, green and other shades may be obtained and several specific combinations are given in the Specification.  In the case of 1-amino-4-(aminoarylamino)-anthraquinones one or both amino groups may be diazotized and coupled.  The dyestuffs may be applied to cellulose esters and ethers in the form of suspensions or dispersions and the latter may be made as described in Specifications 219,349, 224,925, 242,393, 242,711, 269,960, 273,819, 273,820, 322,737, and 323,788, [all in Class 15 (ii), Dyeing, Processes &c. for].  In an example the dyestuff 1-methylamino-4-p-aminophenylaminoanthraquinone --> phenol is described.  Azo dyes, forming on the material.--Anthraquinone derivatives having the 1 : 4 : amino-oxy grouping and also containing an external diazotizable amino group are used for producing azo dyes on the fibre.  Specified diazo components are 1 : 4-aminooxyanthraquinones containing the amino group in an arylamino-, aryloxy- or aracylamino group.  The coupling components specified above may be used but the arylamides of aromatic hydroxy carboxylic acid and the di-b -ketoacidyl diamines are specially suitable. Components of relatively low molecular weight are of interest in the dyeing of cellulose esters and ethers.  Blue, violet and green shades are obtained.  The components may be applied in any desired manner and reference in this respect is made to Specifications 300,929 and 310,779, [both in Class 15 (ii), Dyeing, Processes &c. for]. Dispersions of the components may be made as indicated in the case of the dyes in substance above.  Swelling agents may be used when dyeing cellulose ester and ether materials.  In examples the following dyes are produced on acetate silk (1) 1-oxy-4-p-aminophenylaminoanthraquinone --> diacetoacetyl - o - tolidine (green) or 2 : 3-oxynaphthoic acid-o-toluidide (blue). Other specific combinations are also given.