Patent GB-546383-A (GB)
Title: New wool dyestuffs
IPC: C09B1/28
Filed: 1940-10-08
Abstract: 546,383. Dyes. LODGE, F., LOWE, A., TATUM, W. W., and IMPERIAL CHEMICAL INDUSTRIES, Ltd. Oct. 8, 1940, No. 15012. [Classes 2 (iii) and 15 (ii)] Aminoanthraquinone derivatives suitable for dyeing wool are obtained by treating with an agent adapted to convert amino-alcohol derivatives to their sulphuric esters an anthraquinone derivative carrying in 1 and 4 positions substituents of the general formula <SP>-R-CH(NH)-</SP> R<SP>1</SP>-OH, wherein R and R<SP>1</SP> represent alkyl and alkylene radicals respectively and wherein the anthraquinone nucleus may be substituted by hydroxy or halogen. Specified hydroxy alkylamino residues are those of 2-amino propanol, 3-amino-2-butanol, 2-amino-1-butanol and 3- amino-2-methylbutanol. Specified sulphating agents are sulphuric acid and alkali metal pyrosulphates. In examples, (1) leuco-quinizarin is heated for 24 hours with 2-aminopropanol in isobutanol at 100C., small amounts of piperidine and aqueous sodium hydroxide are added and air is passed through the solution to precipitate a product which dyes cellulose acetate artificial silk bright blue ; this product is then treated with 83 per cent. sulphuric acid to convert it into the sulphuric acid ester which as the sodium salt dyes wool from an acid bath level blue shades very fast to light; (2) the sulphation in (1) is effected by heating for 2 hours with sodium pyrosulphate in dry pyridine at 90C. to obtain the sodium salt of the monosulphuric acid ester similar to that in (1); (3) leuco-quinizarin is heated for 6 hours with 3-amino-2-butanol in aqueous sodium hydroxide at 80C. and the resulting leuco base is boiled with nitrobenzene to obtain a product which dyes cellulose acetate artificial silk blue; this product is then converted into the sulphuric acid ester as in (1) ; (4) leuco-quinizarin is heated for 24 hours with 3-amino-2-methvlbutanol in butanol at 110-115C., a small amount of pyridine is added and air is passed through the solution to obtain a product which dyes cellulose acetate artificial silk blue ; this product is then converted into the sulphuric acid ester as in (1) with an addition of 98 per cent. sulphuric acid to complete sulphation ; (5) leuco-quinizarin is heated for 12 hours with 2-amino-1-butanol in isobutanol under reflux, a small amount of piperidine is added and air is passed through the solution to precipitate a product which is then converted as in (2) into the sulphuric acid ester; (6) leuco-1 : 4 : 5 : 8- tetrahydroxyanthraquinone is heated for 12 hours with 2-aminopropanol in isobutanol under reflux in presence of boric acid, the resulting leuco base is boiled with nitrobenzene containing a little piperidine, and the product is converted as in (2) into the sulphuric acid ester; (7) leuco-1: 4-dimethylamino-anthraquinone or leuco-1 : 4- diaminoanthraquinone or a mixture of both is heated for 12 hours with 2-aminopropanol in isobutanol under reflux in presence of air and the product is sulphated as in (1) ; (8) the sulphation in (2) is effected by heating for 2 hours with an excess of sodium pyrosulphate in dry pyridine at 95-100C. to obtain the disulphuric acid ester ; (9) quinizarin is heated for 6 hours in an atmosphere of nitrogen with 2-aminopropanol in an aqueous solution at 80C. containing sodium hydroxide and sodium hydrosulphite and the product is oxidized with nitrobenzene and sulphated as in (1). Specifications 285,641 and 289,807, [both in Clcass 2 (iii)], are referred to.