Patent GB-400922-A (GB)
Title: Improvements in the manufacture and production of water-soluble azo dye-stuffs
IPC: C09B29/00
Filed: 1932-03-16
Abstract: Azo dyes are made by coupling diazo or tetrazo compounds with an amino and/or hydroxy coupling component to which an aliphatic radicle of at least 10 carbon atoms is attached by means of a -NH-, -COO-, -NHCO-or -NHSO2- group, at least one of the components containing at least one -COOH or -SO3H group, wherein coupling components corresponding to one of the formul  <FORM:0400922/IV/1> and <FORM:0400922/IV/2> (X = a 10 carbon aliphatic radicle) containing a sulphonic group are used only for disazo dyes and for such monoazo dyes as contain a further radicle of at least 10 carbon atoms in the diazo component.  Any diazo compound can be used, e.g. those of the benzene and naphthalene series including aralkyl, hydroxy, alkoxy, halogen, nitro, carboxy and sulpho derivatives, and diamino derivatives of diphenyl, benzophenone, diphenylsulphone, diphenylurea, diphenyleneketone, carbazole, diphenylmethane, diphenylether, stilbene, azobenzene and derivatives thereof.  The dyes are soluble in organic solvents and are suitable for colouring lacquers or artificial masses, e.g. celluloid.  Dyeings are fast to washing and fulling.  In examples, the following dyestuffs are described: (1) 1-naphthylamine-5 : 7-disulpho acid --> p-aminostearic acid anilide of acetoacetic acid (from the anilide and acetoacetic ester), (2) sulphanilic acid --> dodecylaniline (from dodecylchloride and aniline), (3) dianisidine \sQ oleyl H acid; the dyestuff may be treated in substance or in the dye-bath with copper salts; a table is given showing the shades obtained on wool using disazo dyes from the following additional components: tolidine, benzidine - o - disulpho acid, diaminobenzophenone and tolidine-m-disulpho acid; condensation products of oleic acid with 2-amino-8-naphthol-3-sulpho acid, M acid and J acid and the condensation product of stearic acid with H acid; J acid, N-phenyl-J acid, 2-naphthol-6-sulpho acid, condensation product of salicylicsulphochloride and N - methyl - J acid, the 3 - methyl - 1 - phenyl - 5 - pyrazolone from 2<1>-amino - 4<11> - hydroxydiphenylsulphone-4<1>-3<11>-sulphocarboxylic, 2 : 8 - dioxynaphthalene - 6-sulpho acid, 1-naphthol-4-sulpho acid, 3-methyl-1 - phenyl - 5 - pyrazolone, 1-p-sulphophenyl-5-pyrazolone - 3 - carboxylic acid, 1-(2<1>-hydroxy-3<1> - carboxy - 5<1> - sulphophenyl) - 3 - methyl-5-pyrazolone, 1 - phenyl - 5 - pyrazolone - 3-carboxylic acid, (4) 1-naphthylamine-6-sulpho acid --> 1-naphthylamine --> oleyl or stearyl H acid, (5) 4-amino-1 : 3-xylene-5-sulpho acid --> 1-amino-2-methoxy-5-methylbenzene --> oleyl J acid, (6) aniline - 2 : 4 - disulpho acid --> 2 - naphthol - 6 - sulphododecylamide, (7) 1 - naphthylamine - 3 : 6 - disulpho acid --> 4 - methyl - 3 - laurylamidophenol, (8) p-aminosulphosalicylic acid --> dodecylester of 2 : 3-oxynaphthoic acid, (9) monostearyl - p - phenylene diamine --> capryl H acid; monocapryl - p - phenylenediamine --> oleyl H acid, (10) metanilic acid dodecylamide --> capryl H acid, (11) sulphanilic acid --> condensation product from capric anhydride and 1-amino-4-naphthol.  The Provisional Specification describes also the use of coupling components in which the aliphatic radicle is attached directly to the nucleus or by means of -O- and - SO2 - O - linkages and is not restricted.  In examples the following dyestuffs are described: (1) m-chloraniline --> lauryl K acid (suitable for lakes), (2) metanilic acid --> stearyl H acid (3) aniline-2 : 4-disulpho acid --> dodecylaniline, (4) a  - naphthylamine, aniline, 5-amino-2-benzoylamino-1 : 4 - hydroquinonediethylether or 3 - amino - 4 - methoxy-6-benzoylamino - 1 - methylbenzene --> oleyl H acid, (5) metanilic acid --> 1 : 4-naphthohydroquinonemonodecylether, (6) aniline --> 1 - naphthol - 4 - sulphododecylamide (coupled in presence of pyridine).  Acylamino compounds are made by condensing aromatic polyamines or aminohydroxy compounds with aliphatic acids containing at least 10 carbon atoms or halides thereof, e.g. capric, lauric, myristic, palmitic, margaric, stearic, arachidic, oleic, erucic, elaidic, linoleic and the acids present in soya bean oil.  Sulphamino compounds are made from aromatic sulphochlorides and aliphatic amines containing a radicle of at least 10 carbon atoms, e.g. dodecylamine.  Carboxylic acid esters are made by condensing aromatic amino- or hydroxycarboxylic acids with aliphatic alcohols containing a radicle of at least 10 carbon atoms.  Secondary amines are made by condensing aromatic amines with aliphatic alcohols of the above type in presence of hydrochloric acid or with the corresponding alkyl chlorides.  Ethers are made according to the Provisional Specification from aromatic hydroxy compounds and aliphatic alcohols containing at least 10 carbon atoms, e.g. cetyl alcohol.  Reference has been directed by the Comptroller to Specifications 393,966 and 394,343.