Patent GB-529355-A (GB)
Abstract: 529,355. Dyes. SANDOZ, Ltd. May 30, 1939, No. 15927. Convention date, May 30, 1938. [Classes 2 (iii) and 15 (ii)] N-alkyl sulphonic acids of the anthraquinone series which can serve as dyestuffs for the dyeing and printing of 'wool, silk and acetate artificial silk, are prepared by reacting derivatives of anthraquinone containing primary amino groups with preferably a small excess of aldehyde-bisulphites, e.g. bisulphites of formaldehyde and acetaldehyde or components thereof, under acid conditions and in an organic solvent or in a mixture of solvents of which at least one is organic. As derivatives of anthraquinone there are specified 1- and 2-amino anthraquinones, amino-hydroxy-, amino-methoxy-, amino-halogen-, amino-alkylamino-, and amino-acylamino-anthraquinones, amino derivaties of anthra-pyridones, anthrapyrimidones, anthrapyrimidines, anthraquinoneacridones, tri- and tetra-aminoanthraquinones, amino-aryl-aminoanthraquinones, aminodianthrimides and aryl-aminc-anthraquinones with external amino groups. Suitable solvents, which can be mixed with one another and also with water, are dialkyl ethers, the lower alcohols, glycol and glycerine and their ethers, phenol, cresols, acetic acid, propionic acid, benzene, toluene and chloroform. The reaction may be carried out at temperatures lying between ordinary temperature and appreciably above 100‹C., e.g. 120‹C-the solvent may be removed by distillation or steam-distillation : the dyestuff may be obtained by washing free of impurities, e.g. with benzene, and filtering, or by salting-out. In examples, the following compounds are reacted with formaldehydebisulphite solution with phenol as a solvent and in some cases with the addition of a small quantity of sulphuric acid:-1 and -2-aminoanthraquinone (which is also reacted with acetaldehyde-bisulphite), 1-amino-5-, -6-, -7-; and -8-. chlor-anthraquinone, 1-amino-4-hydroxy- and 1 - amino - 4 - methoxy - anthraquinone, 1.4-, 1.5- and 1.8-diaminoanthraquinone, 1.4- diamino-2-methoxy-anthraquinone 1.4.5.8- tetraminoanthraquinone, 1.5-diamino-4.8- dihydroxy-anthraquinone, 1.8-diamino-4.5.- dihydroxyanthraquinone, 1.4.5.-triamino-8- hydroxyanthraquinone, 4.4<SP>1</SP>-diamino-1.1<SP>1</SP>- and 4.4<SP>1</SP>-diamino-1.2<SP>1</SP>-dianthrimide, 4-methylamino-, 4-hydroxyethylamino-, 4-cyclohexylamino-, 1-amino-anthraquinone, 1.4- and 1.5- monobenzoyl- and monoacetyl-diaminoanthraquinone, 1-amino-4-phenylamino-anthraquinone, 1-amino-4-anilido-5-hydroxy-anthraquinone, 1-amino-4-o-, -m- and -p-chloranilico - anthraquinone, 1 - amino - 4 - (2<SP>1</SP>.4<SP>1</SP>-, 21.51- and 3<SP>1</SP>.5<SP>1</SP>-) dichloranilido-anthraquinone, 1 - amino - 4 - m - bromanilido - anthraquinone, 1-amino-4-m-cyan-, -4-m-hydroxy- and -4-mcarboxy-anilidoanthraquinone, 1-amino-4-o-, m- and -p-toluidoanthraquinone, 1-amino-4- o-, and -p-anisidino-anthraquinone, 1-amino- 4-o- and -p-phenetidino-anthraquinone, 1-amino-4-(2.<SP>1</SP>4<SP>1</SP>, 2<SP>1</SP>.5<SP>1</SP>, and 3<SP>1</SP>.5<SP>1</SP>)-xylidinoanthraquinone, 1-amino-4-p-phenoxyanilidoanthraquinone, 1-amino-4-α- and -#-naphthylaminoanthraquinone, 1-amino-4-p-aminophenylamino-anthraquinone, 1-amino-4-benzidinoanthraquinone, 1-methylamino-4-pphenylene-diaminoanthraquinone, 4-aminoanthraquinone-2.1. benzacridone, C-carbethoxy-2- methyl - 4 - amino - anthrapyridone (made according to Specifications 377,419 and 377,632), 4- and 5-amino-anthrapyrimidine and C- carbethoxy - 2 - methyl - 4 - p - phenylenediamino- and -benzidine-anthrapyridone; 1..4- diaminoanthraquinone is reacted with formaldehyde-bisulphite using toluene, diethyl-ether, or ethyl alcohol, alone or in admixture with water or benzene, as solvent, and in the presence of a little sulphuric, hydrochloric or phosphoric acid, sodium bisulphate, ammonium bisulphate, magnesium chloride or aluminium chloride. Specifications 23968/99, [Class 2], 238,717 and 252,922, [both in Class 2 (iii)], also are referred to.