Patent GB-821331-A (GB)
Title: New disazo-dyestuffs and process for their manufacture
IPC: C09B31/14
Filed: 1956-02-29
Abstract: The invention comprises dyestuffs of formula <FORM:0821331/IV(c)/1> where R1 is an aromatic, especially a benzene or naphthalene, residue, R2 is a benzene residue, and R3 is an 8-oxyquinoline residue.  They are made in conventional fashion by coupling an appropriate diazo-azo-compound with an 8-oxyquinoline.  The diazo components may be made by coupling appropriate diazotized amines with the required naphthol sulphonic acids.  All coupling reactions are preferably effected in an alkaline medium with the optional addition of a substance such as pyridine.  R1 may contain a metallizable group in the ortho position to the azo link, specified groups being OH, COOH, OCH2COOH, OC2H4OH, OEt, OMe and OC2H4OSO3H.  The amines may contain substituents such as halogen, alkyl, sulphonamide, carboxylic acid amide or nitro groups, specified amines being 1-amino-2, -3- and -4-methyl-, -2-methyl-4-methoxy- and -b -oxyethoxy-, -3-sulphonamido-, -4-sulpho- and -carboxy-, -2-carboxy-, -2-methyl - 4 - methoxy - 5 - sulpho -, - 4 - acetylamino-2-sulpho-, -2-methyl-4- and -5-carboxy-methoxy-, -2-carboxy-5-methoxy-, -2-methoxy-5 - methyl -, - 2 - methoxy - 5 - methyl - 4 - sulpho - and - 2 - carboxymethoxy - 5 - chloro- and -methyl-benzenes, sulphuric acid esters of 1 - amino - 2 - methyl - 4 - b  - oxyethyl - and 1 - amino - 2 - b  - oxyethoxy - 5 - methylbenzenes, and the latter compound itself, 2-aminophenol - 4 - carboxylic acid phenylamide and its sulphonic acid, 2-naphthylamine-3-carboxylic acid and its 6-sulphonic acid. The residue NH-OC-R2-NH2 may be <FORM:0821331/IV(c)/2> where one Y is a methyl group or H and the other Y is an amino group.  Preferably the Y p to NHOC is an amino group.  Specified naphthol sulphonic acids are 2-(31- and 41-aminobenzoylamino) and (31-methyl-41-aminobenzoylamino) - 5 - naphthol - 1,7 - disulphonic acids.  Preferred oxyquinolines are those which couple in 5-position, e.g. 8-oxyquinoline-7-sulphonic and -carboxylic acids, 6-methoxy-8-oxyquinoline, 6,8-dioxyquinoline and 8-oxyquinoline. Advantageously the dyestuffs contain 2-4, preferably 2-3, groups imparting solubility in water, e.g. only the two SO3H groups of the naphthalene residue or, in addition thereto, a COOH group in residue R1, or an SO3H group in R1 or R3.  The dyestuffs may be used for dyeing or printing wool, silk or leather but have particular application for cellulosic materials.  They may be converted in substance or on the fibre into complex metal compounds, Cu, Cr, Fe, Ni or Co being specified metals.  The metal compounds, especially those of copper, are advantageously made in a substratum when the metal-free dyestuff is of poor affinity and/or when the metal complex is sufficiently soluble.  Dyestuffs yielding sparingly-soluble metal compounds are advantageously metallized on the fibre or partially on the fibre and partially in the dye bath as, e.g. in Specification 455,274, [Group IV].  The metal-free dyeings may also be coppered as in Specification 619,969.  In examples, which illustrate the preparation of the dyestuffs and their use in dyeing cotton in red shades the components used are chosen from those specified above with the addition of dehydrothioparatoluidine sulphonic acid and 2-methoxyaniline and its 5-sulphonic acid as diazo components