Patent GB-646888-A (GB)
Title: Azo compounds containing a thiazolone cyanine dye component
IPC: C09B23/04
Filed: 1948-06-14
Abstract: Azo dyestuffs are manufactured by coupling a diazotized amine with a thiazolone cyanine dye of the general formula <FORM:0646888/IV (c)/1> wherein A represents the residue of a 5- or 6-membered heterocyclic nitrogenous nucleus (e.g. oxazole, thiazole, selenazole and their polycyclic derivatives such as those of the benzene, naphthalene, acenaphthene and anthracene series, pyridine and its polycyclic derivatives such as quinoline and a  : b -naphthaquinolines, indolenines, diazines such as pyrimidines and quinazolines, thiazolines and selenazolines, the polycyclic compounds being optionally substituted in the carbocyclic rings by one or more groups such as alkyl, aryl, amino, hydroxy, alkoxy or methylenedioxy, or halogen atoms), n is 1 or 2, R1 represents an alkyl (e.g. methyl, ethyl or propyl), allyl, aryl (e.g. phenyl, naphthyl or tolyl) or aralkyl (e.g. benzyl) group, R2 represents an aliphatic radical (e.g. methyl, ethyl, propyl, butyl, hydroxyethyl or ethoxyethyl) or an aralkyl radical (e.g. naphthylmethyl or benzyl), and X represents an acid radical (e.g. chloride, bromide, iodide, alkyl sulphate, p - toluenesulphonate or perchlorate).  The coupling components are obtainable by the process of Specification 646,900, and the products of certain of the examples thereof are employed as coupling components in the examples of the present Specification. Specified diazo components, some of which are employed in the examples, are: aniline and its p-chloro-, 2 : 5-dichloro-, o- and p-nitro-, 2-nitro-4-chloro- and 2 : 4-dinitro-derivatives, p-toluidine, o-anisidine, aminoazobenzene, a -naphthylamine, 3-nitro-4-toluidine, sulphanilic acid, aniline - 2 : 5 - disulphonic acid, 1 - amino - 2 - naphthol-6-sulphonic acid, p-aminodiphenylamine, benzidine and its 2 : 21-dimethyl-, 2-ethoxy-, 3 : 31-dichloro- and 2-nitro-derivatives and 2 : 21-disulphonic acid, dianisidine, o : o1-diaminodiphenic acid, 1-naphthylamine-6- and 7-sulphonic acids, 2-chloro-4-aminobenzoic acid, 2-amino-4-sulphobenzoic acid, primuline, 2 : 6-diaminotoluene - 4 - sulphonic acid, 3 - aminobenzoic acid, 2 - amino - 8 - naphthol - 3 : 6 - disulphonic acid, 1 : 4-diaminonaphthalene-3-sulphonic acid, 2-naphthylamine-3 : 6-disulphonic acid, p-aminobenzyldiethylamine, 2 : 7-diaminocarbazole, 4 : 41 - diaminostilbene - 2 : 21 - disulphonic acid, 4 : 41-diamino-2 : 21-dimethyltriphenylmethane, 2 - aminobenzthiazole and its 6-ethoxy-derivative, 2-aminobenzoxazole, 4 : 41 - diaminodiphenylurea - 3 : 31 - disulphonic acid, 4 : 41 - diaminodiphenylmethane, 2 - (p - aminophenyl) - 6 - methylbenzthiazole and 4-aminoperimidine - 5 : 8 - disulphonic acid. The products are useful in photography (see Group XX) and for dyeing textile materials such as wool, cotton, silk and cellulose acetate artificial silk.  In particular the water-insoluble dyes, dispersed in water with the aid of a dispersing agent, e.g. soap, may be applied by dyeing, printing or stencilling to hydrolysed or unhydrolysed cellulose esters (including mixed esters) and cellulose ethers.  The dyestuffs may also be formed on cotton fabrics by impregnation with an aqueous solution of the thiazolone cyanine dye and development in a neutral solution of a diazonium salt.