Patent GB-467815-A (GB)
Title: Manufacture of dyestuffs of the anthraquinone series
IPC: C09B55/00
Filed: 1935-10-23
Abstract: Dyes are made by reacting an anthraquinone containing a reactive amino group with a cyanuric halide, or with a derivative thereof resulting from the substitution of one or two of its halogen atoms by another radical or radicals, the components being so selected that at least one of them contains at least one sulphonic or carboxylic group.  Products prepared as above which still contain reactive halogen may be reacted with a compound containing a reactive amino-group.  The products of the above processes, if they still contain a reactive amino-group, may be reacted with a halide or anhydride of an organic acid.  The amino group in the anthraquinone may be attached directly to the anthraquinone nucleus or to a side-chain or external group such as benzoyl or phenyl.  The above products dye regenerated cellulose, animal and vegetable fibres violet or greenish-blue tints, and are used for pigments and for colouring lacquers and artificial masses.  In examples, cyanuric chloride is condensed with (1) 2 mols. 1.4-diaminoanthraquinone-2.6-disulphonic acid in succession, followed by aniline, (2) 1.4-diaminoanthraquinone-2.6-disulphonic acid, followed by 2-amino-5-oxynaphthalene-7-sulphonic acid and aniline, (3) 1 - amino - 4(p - aminophenylamino)anthra-quinone-2-sulphonic acid, followed by 2-amino-5-oxynaphthalene-7-sulphonic acid (or 2-(3<1> or 4<1> - amino) - phenylamino - 5 - oxynaphthalene - 7-sulphonic acid, 2-(3<1> or 4<1>-amino)-benzoylamino - 5 - oxynaphthalene - 7 - sulphonic acid, or dehydrothiotoluidine-sulphonic acid), and aniline or another amino-compound such as methylamine, monomethylaniline, cyclohexylamine, m or p-phenylene diamine, benzidine or a homologue of aniline such as a toluidine or a xylidine or a substitution product thereof, (4) the condenstion product from 1-amino-4-bromoanthraquinone - 2 - sulphonic acid and benzidine, followed by methylamine, (5) the condensation product from 1-amino-4-brom-anthraquinone-2-sulphonic acid and m-phenylenediamine, followed by the condensation product from 1 - amino - 4 - bromanthraquinone - 2 - sulphonic acid and benzidine, followed by aniline, (6) the condensation product from 1 - amino - 4 - bromanthraquinone - 2 - sulphonic acid and p-phenylene diamine, followed by m-phenylenediamine and aniline (the p-phenylenediamine may be replaced by m-phenylenediamine or its sulphonic acid, or diaminostilbene-disulphonic acid, p-diaminodiphenylamine, or benzidine-disulphonic acid).  In a final example cotton is dyed, using the dyestuff obtained as in (3) above.  Samples have been furnished under Sect. 2 (5) of products prepared from cyanuric chloride and the following compounds: (a) 1-amino-4(4<1>-amino) - phenylaminoanthraquinone - 2.3<1> disulphonic acid (2 mols.) and p-phenylenediamine, the product being treated with cinnamic acid chloride; (b) 1-amino-4(4<1>-amino) - phenylaminoanthraquinone - 2.3<1> - disulphonic acid, 2 - amino - 5 - oxynaphthalene - 7-sulphonic acid and p-phenylenediamine, the product being acetylated; (c) same compounds as under b, but the product is benzoylated instead of acetylated; (d) 1-amino-4-(4<1>-amino) - phenylaminoanthraquinone - 2 . 3<1> - disulphonic acid, 1 - amino - 4 - (4<1> - amino) - phenylaminoanthraquinon - 2 - sulphonic acid and p-phenylenediamine, the product being acetylated; (E) same compounds as under D, but the product is benzoylated instead of acetylated; (F) phenol, 2-amino-5-oxynaphthalene - 7 - sulphonic acid and 1 - amino - 4(4<1> - amino) - diphenylaminoanthraquinone - 2 - sulphonic acid; (G) phenol, 1-amino-4(4<1>-amino)-phenylaminoanthraquinone - 2.3<1> - disulphonic acid and 1 - amino - 4(4<1> - amino) - diphenylaminoanthraquinone-2-sulphonic acid.  Specification 221,843, [Class 2 (iii)], is referred to.  The Specification as open to inspection under Sect. 91 comprises the use of polybasic organic acid halides generally in addition to cyanuric halides.  Halides specified are phosgene, terephthalic and isophthalic acid dichlorides, the dichloride of phenylenedioxy-acetic acid, dichlorophthalazine, dichloroquinoxaline, tribromopyrimidine, carbon bisulphide (if desired as mustard oil).  In addition to anthraquinones are included dibenzanthrones, pyranthrones, pyrazolanthrones, anthanthrones, anthrapyridones, and dibenzpyrenequinones. Specification 466,886 is referred to.  This subject-matter does not appear in the Specification as accepted.