GB542594A - Manufacture of anthraquinone dyestuffs - Google Patents

Abstract

542,594. Dyes. IMPERIAL CHEMICAL INDUSTRIES, Ltd. (Du Pont de Nemours & Co., E. I.). May 15, 1940, No..8695. [Class 2 (iii)] Trianthrimide monocarbazoles of the general formula in which Aq stands for an anthraquinone nucleus, and AQ for an anthraquinone or benzoylaminoanthraquinone residue are made (1) by inter-acting 1 : 6-dichloranthraquinone with an equimolecular proportion of an amine AQNH 2 , ring-closing to the carbazole with aluminium chloride, and inter-acting the carbazole with the same or a different amine AQ.LNH 2 , (2) by inter-acting 1-amino-6-chloranthraquinone with an equimolecular proportion of AQ C1, ring-closing to the carbazole with aluminium chloride, and inter-acting the carbazole with an amine AQNH 2 , or (3) interacting 1: 6-dichloranthraquinone with two molecular proportions of the same or different amines of the formula AQNH 2 and ring-closing to a monocarbazole with aluminium chloride at a relatively low temperature. The products are vat dyes dyeing cotton in brownish and orange shades. In examples (1) 1 : 6-dichloranthraquinone is condensed with 1-aminoanthraquinone (1 mol.) fused with an aluminium chloride-sodium chloride mixture, and the product condensed with 1-aminoanthraquinone or 1-amino-5-benzoylaminoanthraquinone, (2) 1 : ,6-dichloranthraquinone is condensed, with 1-amino-4 or 5-benzoylaminoanthraquinone (1 mol.) in nitrobenzene, aluminium chloride is then added and the mixture heated to form the carbazole which is then condensed with 1-amino-4 or 5- benzoylami noa nthra qui none, and (3) 1-6 dichloranthraquinone is condensed with 1-amino-4 or 5-benzoylaminoanthraquinone (2 mols, or 1 mol. of each may be used) and the resulting trianthrimide is converted to the monocarbazole by heating with aluminium chloride in nitrobenzene;