Patent GB-713580-A (GB)
Title: Green substantive dyestuffs of the anthraquinone series and process for their manufacture
IPC: C09B43/36
Filed: 1952-04-21
Abstract: Green substantive dyestuffs of the formula <FORM:0713580/IV(c)/1> where R is a benzene or diphenyl residue, X is hydrogen, alkyl, alkoxy or sulphonic acid, M is hydrogen, lithium sodium or potassium, one B is hydrogen, methyl, chlorine or bromine, the other B is hydrogen, W is the residue of an azo compound, and the nucleus 1 may be substituted by halogen (in 6 and/or 7 position) or by one sulphonic acid group, are prepared (in admixture with the two corresponding symmetrical dyestuffs) by condensing a halide Hal-CO-CB = CB-CO-Hal with the two appropriate amino compounds.  When the amino-azo compounds contain metallisable groupings these may be metallised before or after the condensation; suitable metals are copper, chromium, iron, cobalt, nickel, manganese and aluminium.  In examples the following pairs of compounds are condensed with fumaric dichloride:-(1) 4-aminoazobenzene-4-sulphonic acid and the condensation product from 1-amino-4-bromoanthraquinone-2-sulphonic acid and benzidine-3-sulphonic acid, (2, 4-aminoabenzene-4\sv-sulphonic acid and the condensation product from 1-amino-4-bromoanthraquinone-2 : 6-disulphonic acid (lithium salt) and benzidine, (3) the condensation product of (1) and the dyestuff 4-aminoazobenzene-3 : 4\sv -disulphonic acid --> m-toluidine, (4) 1-amino-4-(p-aminoanilino)-anthraquinone-2-sulphonic acid (lithium salt) and the dyestuff 2-naphthalamine-4 : 8-disulphonic acid --> acetyl-m-phenylene diamine, (5) the anthraquinone compound of (4) and the disazo dyestuff of (3), (6) 1-amino-4-(p-aminoanilino)-anthraquinone-2 : 6-disulphonic acid and the p-aminobenzoyl derivative of the disazo dyestuff of (3), (7) the anthraquinone compound of (4) and the dyestuff of (6), (8) the anthraquinone compound of (4) and 4-aminoazbenzene-4\sv-sulphonic acid, (9) the anthraquinone compound of (1) and 4-amino-2\sv : 3-dimethylazobenzene-4\sv-sulphonic acid, (10) the anthraquinone compound of (1) or (4) and the dyestuff 5-sulphoanthranilic acid --> 1-(p-aminophenyl)-3-methyl-5-pyrazolone; the product may be coppered or the copper derivative of the azo dye may be used, (11) the anthraquinone compound of (1) or (4) and 4-amino-4\sv-hydroxyazobenzene-3\sv-carboxylic acid; dyeings on cellulosic fibres may be metallised, (12) the anthraquinone compound of (4) and the dyestuff <FORM:0713580/IV(c)/2> (13) the condensation product of benzidine with 1-amino-4-haloanthraquinone-2 : 5-or-2 : 8-disulphonic acid and the azo dye of (12), (14) the anthraquinone compound of (4) and the dyestuff 3-(p-aminobenzoylamino)-5-sulphosalicylic acid --> m-toluidine and (15) the anthraquinone compound of (4) and the azo dye of (9).  In further examples (16) the anthraquinone compound of (1) and the azo dye of (14) are condensed with maleic dichloride, and (17) 1-amino-4-(p-amino-anisidino or-toluidino)-antraquinone-2-sulphonic acid and the azo dye of (10) are condensed with mesaconic dichloride. There may be used also the dichlorides of chlorofumaric and bromofumaric acids and the dibromides of any of the acids mentioned. Other dyestuff components are mentioned, of which the azo dye may be monoazo or disazo of the benzene, naphthalene, stilbene, pyrazolone or acetoacetic arylide series.  Additional examples are given of the use of the products:-(18) cotton is dyed green with the product of (15); (19) cotton is dyed with the product of (11) and after-coppered or after-chromed; (20) cotton or viscose is dyed with the product of (12).  Specification 554,463 is referred to.