Patent GB-924660-A (GB)
Title: New azo dyestuffs containing dihalogenpyridazone groups
Inventor: HENSEL HANS RUPRECHT
IPC: C09B62/16
Filed: 1960-06-24
Abstract: Pyridazone compounds used in the preparation of azo dyes (see Group IV(c)) are prepared by heating hydrazines with mucochloric or mucobromic acid.  Nitro and acylamino groups in the pyridazone compounds may be converted into amino by reduction or hydrolysis, the nitro groups being introduced by nitration of the pyridazone compounds in some cases.  Compounds prepared in this manner in examples are 1-(31-nitro- or -acetylamino- or -amino-phenyl)-4:5-dichloropyridazone-(6), 1-(4-acetylamino- or -amino-phenyl)-4:5-dichloropyridazone-(6), 1-(3-amino-6-sulphophenyl)-4:5-dichloro- or -dibromo-pyridazone-(6), 1-(4-methyl-2- or -3-aminophenyl)-4:5-dichloropyridazone-(6), 1-[41-(411-nitro- or -amino-211-sulpho-styryl)-31-sulphophenyl] - 4:5-dichloropyridazone-(6), 1-(4-sulphophenyl)- or -(2-nitro-or -amino-4-sulphophenyl)-4:5-dichloropyridazone-(6) and 1-(2-methoxy-4-amino-5-sulphophenyl)-4:5-dichloropyridazone-(6). Further compounds are prepared by condensing the acid chloride of 1-(4-carboxyphenyl)-4:5-dichloropyridazone-(6) with various amino compounds.  Products specified in examples are 1-X-8-naphthol-3:6-disulphonic acid, 6-X-1-naphthol-3-sulphonic acid and 3-or 4-X-6-sulpho-aniline wherein x is a 4-(4:5-dichloro-6-keto - pyridazinyl) - benzoylamino group.  Intermediate hydrazones prepared in examples are the 3-acetylaminophenyl- and 3-acetylamino - 6 - sulphophenyl - hydrazones of mucochloric acid.  1- (41- aminobenzenesulphonamidophenyl)-4 : 5-dichloropyridazone-(6) is repared by condensing 1-(4-aminophenyl)-4:5-dichloropyridazone-(6) with 4-acetylaminobenzensulphonyl chloride followed by hydrolysis of the amino group.  41-nitro-4-hydrazino-stilbene-2:21-disulphonic acid is prepared by diazotisation of the corresponding 4-amino-compound and reduction of the diazo compound with stannous chloride and hydrochloric acid.  The acid chloride of 1-(4-carboxyphenyl)-4 : 5-dichloropyridazone-(6) is prepared by heating the acid with thionyl chloride in nitrobenzene.ALSO:The invention comprises dyes of formula <FORM:0924660/IV(a)/1> wherein A is the radical of an aromatic or arylazoaromatic diazo component, B is the radical of an aliphatic, aromatic, arylazoaromatic or heterocyclic coupling component including a component of the tetrazaporphin series and in which only one of the radicals A and B is an arylazoaromatic radical, D is a direct covalent linkage, <FORM:0924660/IV(a)/2> group, X is a chlorine or bromine atom and n is 1 or 2; and metal complexes thereof.  The dyes are prepared by diazotization and coupling procedures using suitable components.  Specified metal complexes are copper, chromium and cobalt complexes prepared by known methods.  The dyes may be used for dyeing and printing wool, synthetic polyamides and cellulose fibres in conjunction with an acid-binding agent.  In examples: (1) the dyestuff 1-(4-aminophenyl)-4, 5-dichloropyridazone-(6)-->1-(2-methyl-4- sulphophenyl) -3-methyl-5-pyrazolone is prepared; (2) the dyestuff 1-(3-amino-6-sulphophenyl)-4:5-dichloropyridazone --> 1 - naphthol - 4 - sulphonic acid is coppered oxidatively; (3) the dyestuff 1-(4-methyl-2-aminophenyl)-4, 5-dichloropyridazone - (6) --> 2 - amino - 4 - acetylaminobenzenesulphonic acid-->1-(2-chloro-5-sulphophenyl)-3-methyl-5-pyrazolone is prepared; (4) 1-(3-amino-6-sulphophenyl) - 4, 5 - dichloropyridazone-(6) is diazotized and coupled with the compound of formula <FORM:0924660/IV(a)/3> Many further examples are specified. Specification 660,447 is referred to.