Patent GB-726726-A (GB)
Title: Improvements in or relating to dis- and polyazo dyestuffs
IPC: C09B43/145
Filed: 1953-06-08
Abstract: The Specification comprises (1) condensing a dicarboxylic acid halide Hal-CO-CX = CH-CO-Hal (X = hydrogen, chlorine, bromine or methyl) with 1 mol. of an aminoazo compound of the formula <FORM:0726726/IV (c)/1> and 1 mol. of the same or a different aminoazo compound or of an amino compound which is capable (after the condensation) of coupling with a diazonium salt (R is a benzene or naphthalene residue which may contain further azo groups); (2) preparing the disazo and polyazo dyestuffs of (1) by coupling 2 mols. of the appropriate diazonium salts simultaneously or successively with the dicarboxylic acid bis-(pyrazonyl-stilbene amide); and (3) the products so obtained, those covered by the parent Specification being excluded. When R contains an o-metallizable group the dyestuff can be metallized in substance or on the fibre; alternatively, metallization may be effected before the condensation.  The products of (1) or (2) may be coupled with diazonium salts.  The condensation of (1) is carried out in water at 0-30 DEG  C. in the presence of an acid binding agent and, if desired, an inert solvent.  A slight excess of acid halide is used to compensate for losses due to hydrolysis.  When two different amines are condensed they may be taken in any proportions and the product will be a mixture of three products. Similarly, in method (2) the two diazo components may be used in any proportion.  The products are suitable for dyeing cotton and regenerated cellulose. In the examples, the following are condensed with fumaric dichloride: (1) 2 : 5-diaminotoluene --> anthranilic acid --> 1-(p-sulphophenyl)-3-methyl-5-pyrazolone and anthranilic acid --> 4-amino-41-(311-methyl-511-pyrazonyl-111) - stilbene - 2 : 21 - disulphonic acid; (2) the copper derivative of chromotropic acid \sM o-dianisidine --> H acid and 5-sulphoanthranilic acid --> same stilbene derivative as in (1); (3) 5-amino-3-sulphosalicylic acid --> m-aminoacetanilide and azo-stilbene derivative of (1); (4) 3-aminopyrenedisulphonic acid --> m-toluidine and azo-stilbene derivative of (2); (5) 5-sulphoanthranilic acid --> 1-(p-aminophenyl)-3-methyl-5-pyrazolone and azostilbene derivative of (2); after-coppered; (6) 5-aminoanthranilic acid --> acetoacetanilide-m-sulphonic acid and azostilbene derivative of (1); (7) 2 mols. of anthranilic acid 5-sulphomethylamide --> stilbene derivative as in (1); after-coppered and nickeled; (8) 2 mols. of sulphanilic acid --> stilbene derivative as in (1); (9) 2 mols. of sulphanilic acid --> amino-p-cresol --> stilbene derivative as in (1); (10) 2 mols. of copper complex of 2-hydroxy-6-nitro-1-naphthylamine-4-sulphonic acid --> stilbene derivative as in (1); (11) 2 mols of 5-aminosalicylic acid --> anthranilic acid --> stilbene derivative as in (1).  In additional examples: (12) the dyestuff 5-aminoanthranilic acid --> acetoacetanilide-m-sulphonamide and the azo-stilbene derivative of (2) are condensed with maleic dichloride; (13) the stilbene derivative of (1) and the azostilbene derivative of (7) are condensed with fumaric acid dichloride and the product coupled with diazotized anthranilic acid 5-sulphomethylamide, giving the same product as in (7); (14) 2 mols. of anthranilic acid 5-sulphomethylamide \sQ bis-amide of fumaric acid with 4-amino-41-(311-methyl-511-pyrazonyl-111) -stilbene-2 : 21-disulphonic acid; converted into nickel complex; (15) 2 mols. 2-aminophenol-4-sulphonamide \sQ bis-amide of (14); (16) 2 mols. of (sulphanilic acid --> cresidine) \sQ bis-amide of (14), coppered under dealkylating conditions; product is same as that of (a); (17) cotton is dyed with the product of (1) and after-coppered; (18) cotton is dyed with the copper derivative of (5).  A table is given of other dyestuffs obtained by the condensation method, and other suitable components are mentioned.