Patent GB-515066-A (GB)
Abstract: 515,066. Dyes. SOC. OF CHEMICAL INDUSTRY IN BASLE. May 23, 1938, Nos. 15312 and 15313. Convention dates, May 22, 1937 and May 5, 1938. [Classes 2 (iii) and 15 (ii)] Azo dyes are made by combining the halides of carbonic and thiocarbonic acids, such as phosgene and thiophosgene and the halides of heterocyclic nitrogen compounds of the type represented by cyanuric acid, quinazoline and pyrimidine with a coupling component, which on the one hand, is capable of coupling with diazo compounds to yield azo dyes owing to the presence of a 5-pyrazol�ne ring, and, on the other hand, contains in the 1-position of this ring an amino-substituted phenyl radical, coupling the product thus obtained with a diazo compound substituted in o-position to the diazo-group by OH or COOH or by a substituent capable of conversion into such a group and converting the dyestuff thus obtained into a complex copper compound. Alternatively the diazo compound may be coupled with the pyrazolone and the dyestuff treated in any order with an agent yielding copper and the organic halide, if necessary after converting into an amino group a group capable of such conversion in the 1-phenyl residue of the pyrazolone. The treatment with the agent yielding copper may be conducted simultaneously with the production of the azo dye. In the first process described above using an o-oxy- or o-carboxy-diazo compound the coppering may be carried out on the fibre. The products yield yellow to orange and brown shades on cotton, ramie, linen and cuprammonium or viscose artificial silk. In examples (1) the dye 1-amino-4-sulphobenzene-2-carboxylic acid ## the urea from 1-(3<1>- or 4<1>-aminophenyl)- 3-methyl-5-pyrazolone is treated with ammoniacal copper sulphate' in substance or on the fibre or the coupling to form the dye may be conducted in presence of a copper salt, (2) the dye 1-amino-4-sulphobenzene-2-carboxylic acid# 1-(4<1>-aminophenyl)-5-pyrazolone- 3-carboxylic acid is treated with phosgene and treated with a copper compound as above, (3) the dye 1-amino-4-sulphobenzene-2-carboxylic acid ## the secondary condensation product from cyanuric chloride (1 mol.) and 1- (31 - aminophenyl) - 5 -pyrazolone - 3 -carboxylic acid (2 mols.) is coppered as above ; the same dye is made by condensing, 1-amino-4-sulphobenzene-2-carboxylic acid# 1-(31-aminophenyl)- 5-pyrazolone-3-carboxylic acid with cyanuric chloride and coppering. Examples of dyeing processes are given. Other components specified are anthranilic acid, 1-aminobenzene-4- nitro-2-carboxylic acid, 1-amino-4-chlor- or 4- nitro-2-oxybenzene, 1-amino-2-oxybenzene-4- sulphonic acid, 1-amino-2-chlor- or 2-methoxybenzene-4- or 5-sulphonic acid, 1-amino-2- naphthol-4-sulphonic acid, 2-amino-1-naphthol- 4 : 8-disulphonic acid ; the ternary condensation product from cyanuric chloride (1 mol.), 1-(4<1>-aminophenyl-5-pyrazolone-3-carboxylic acid (2 mols.) and aniline (1 mol.).- Specifications 209,723, 268,754 and 298,494, [all in Class 2 (iii)], are referred to. The Specification as open to inspection under Sect. 91 comprises the use in the above processes of a halide of a polybasic organic acid or an analogue thereof and of a 5-pyrazolone which contains an aromatically bound amino group. The diazo compounds are described as those which are substituted in o-position to the diazo group by a group which is capable of forming complex metal compounds in combination with the enolisable CO-group of the pyrazolone. The dyes may be converted into any complex, metal compound, e.g., a compound of nickel, cobalt, iron, copper, chromium, manganese in substance or on the fibre. This subject-matter does not appear in the Specification as accepted.