Patent GB-533364-A (GB)
Title: Manufacture of azo-dyestuffs
IPC: C09B39/00
Filed: 1939-08-11
Abstract: 533,364. Azo dyes. SOC. OF CHEMICAL INDUSTRY IN BASLE. Aug. 11, 1939, Nos. 23196 and 23197. Convention dates, Aug. 16, 1938 and July 28, 1939. [Classes 2 (iii). and 15 (ii)] Triazo or polyazo dyes are prepared by coupling diazo compounds with coupling components and/or by linking azo dyestuffs with one another or with suitable compounds, the components being so selected that the finished dyestuff contains at least once the grouping =C-C<SP>11</SP>-N=C<SP>1</SP>-H as part of the tins I OH condensed nuclei of 8-hydroxyquinaline and is sufficiently soluble for application in an aqueous medium. The products may be used for dyeing or printing wool, silk, leather, cotton, linen or regenerated cellulose fibres and as pigments ; they yield metal complex compounds on treatment in substance or on the fibre with agents yielding metal, e.g., iron, chromium, nickel, cobalt or copper and the components may be so chosen as to impart an enhanced affinity for vegetable fibres, various components suitable for this purpose being specified. Examples (1) to (9) relate to the production of the following dyestuffs :- (1) 4 - - aminophenol - 2 - carboxylic acid # 1 : 7 - aminonaphthalenesulphonic acid # 1 : 7 or 1 : 6 - aminonaphthalenesulphonic acid # 8-hydroxyquinoline, yielding on vegetable or regenerated cellulose fibres blue dyeings which become fast to washing and to light on after-treatment with a copper salt ; (2) salicylic acid # benzidine # 1 : 6 - aminonaphthalenesulphonic acid # 8-hydroxyquinoline, yielding on cotton brown dyeings which may be aftercoppered ; (3) benzidine - 3 : 3<SP>1</SP> - dicarboxylic acid <SP>#</SP> #  1 : 6 - aminonaphthalenesulphonic acid (2 mols) <SP>#</SP> #  1 : 7 - aminonaphthalenesulphonic acid (2 mols.)<SP>#</SP> #  8 - hydroxyquinoline (2 mols.), yielding on cotton grey dyeings which may be after-coppered ; (4) the product obtained by reduction with glucose, as described in Specification 491,551, of the nitro groups of the dyestuff, 5 - nitro - 2 - aminophenol # (alkaline) 2 : 5 : 7 - aminonaphtholsulphonic acid # 8 - hydroxyquinoline, yielding on cotton, on aftercoppering, blue-grey dyeings fast to washing and to light; (5) the product obtained by similar reduction of the corresponding dyestuff in which the end componet is 8-hydroxyquinoline - 7 - sulphonic acid, yielding on cotton grey dyeings which may be after-coppered ; (6) salicylic acid # benzidine - 3 : 3<SP>1</SP> - dicarboxylic acid # (alkaline) 2 : 5 : 7 - aminonaphtholsulphonic acid # 8 - hydroxyquinoline, yielding on cotton, on after-coppering, violet-blue dyeings ; (7) salicylic acid # benzidine # 1 - amino - 2 - methoxynaphthalene - 6 - sulphonic acid - 8 - hydroxyquinoline, yielding on cotton, on after-coppering, blackish-brown dyeings ; (8) and (9) salicylic acid # benzidine # 1 : 6 - aminonaphthalenesulphonic acid # 8 - hydroxyquinoline - 7- and 5 - sulphonic acids respectively, yielding on cotton, on aftercoppering, red-brown dyeings. Examples are also given of the coppering in substance and on cotton fibre in a fresh bath of the dyestuff of Example 3 and on cotton fibre in the dyebath of the dyestuff of Example (1).Additional specified components are (a) diazo components, aminosulphonic acids of the benzene series, anthranilic acid, 1 : 4 - and 1 : 5 - aminonaphthalenesulphonic acids, 2 : 4 : 8 - and 2 : 6 : 8 - aminonaphthalenedisulphonicacids, O-esters of 1 : 8 - aminonaphtholsulphonic acids, dehydrothiotoluidine and such as contain an 8-hydroxyquinoline residue, (b) tetrazo components, tolidine, dianisidine, 4-nitraniline or its 2- sulphonic acid, (nitro groups reduced) 4- acetylaminoaniline or 1 - amino - 4 - acetylaminonaphthalene - 6 - sulphonic acid (acetylamino groups saponified), diaminostilbenedisulphonic acid and 4 : 4<SP>1</SP> - diaminodiphenylurea, (c) middle components, aniline (as the #- methanesulphonic acid), m-toluidine, cresidine, 2 : 5 - dialkoxyanilines, 5 - amino - 8 - hydroxyquinoline, 1 - aminonaphthalene, 1 - amino - 2 - methoxy - or ethoxy-naphthalene and their 6- or 7-sulphonic acids and 2 : 8 : 6 - aminonaphtholsulphonic acid, (d) end component, 2 : 8 : 6 - aminonaphtholsulphonic acid and halogen-substituted 8-hydroxyquinolines. The linking of components by means of phosgene or halogenated triazines is also specified. Specifications 455,274, 458,501, 468,362 and 497,350 also are referred to.