GB808603A - Improvements in or relating to blue substantive dyestuffs of the anthraquinone series - Google Patents

Abstract

The invention comprises blue substantive dyes which are the ammonium, alkali-metal or amine salts of the acids of the formula: <FORM:0808603/IV (c)/1> where R is paraphenylene or a -C6H4-CO-HN-C6H4-radical, the valencies of the phenylene rings being in the para positions, which may be substituted by alkyl groups of 1 to 4 carbon atoms and/or a sulphonic acid group, the nucleus A may be substituted by a sulphonic acid group or one or two halogen atoms, and the nucleus B may be further substituted, for example by alkyl groups of 1 to 4 carbon atoms, nitro, amino, acylamino and sulphonic acid groups. The dyes are made by reacting 2 mols. of a salt of an acid of the formula <FORM:0808603/IV (c)/2> where R and A are as above, or 2 mols. of a mixture of two or more compounds of this formula, with 1 mol. of an appropriate benzene-1 : 3-dicarboxylic acid halide. The dye containing an amino group in nucleus B may also be made by reducing the corresponding nitro compound with a sulphide. The condensation reaction may be conducted in water at 0-80 DEG C., the acid halide being added in carbon tetrachloride, chloroform, toluene, chlorobenzene or 1 : 2-dichlorobenzene solution, and the pH being maintained between 6 and 11 either by addition of sodium acetate or lithium, sodium or potassium carbonate or hydroxide or by the presence of buffers such as sodium or potassium bicarbonate, sodium tetraborate, disodium phosphate, or magnesium oxide or carbonate. The dye is salted out or precipitated by acidification and kneaded with ammonia, lithium, sodium or potassium carbonate or hydroxide, or amines such as methylamine, ethanolamine or triethanolamine to form the corresponding salts. The dyes colour cotton, hemp, linen, ramie, sisal, fibres and films of regenerated cellulose, straw and paper bright blue shades. As starting materials, the anthraquinone derivatives specified are salts of 1 - amino - 4 - (41 - amino) - phenylaminoanthraquinone - 2 - mono - or - 2.5 -, - 2.6 -, 2.7-, -2.8-, or -2.31-disulphonic acid, 1-amino-6-(7)-chloro-, -bromo-, or -fluoro-4-(41-amino)-phenylaminoanthraquinone - 2 - mono - or - 2,31 - disulphonic acid, 1 - amino - 6,7 - dichloro - 4 - (41 - amino) - phenylaminoanthraquinone - 2 - mono - or - 2,31 - disulphonic acid, 1 - amino - 4 - [41 - (411 - amino) - benzoylamino]-phenylaminoanthraquinone-2,5-, -2,6-, -2,7- or -2,8-disulphonic acid, and 1-amino-4-(31-methyl-41 - amino) - phenylaminoanthraquinone - 2 - sulphonic acid. Benzene - 1,3 - dicarboxylic acid halides mentioned are benzene-1,3-dicarboxylic acid chloride and bromide, 4-methyl-, 5-nitro, 5-acetylamino-, and 5-sulpho-benzene-1,3-dicarboxylic acid chloride. Examples are given.