GB452424A - Manufacture of dyestuffs of the anthraquinone series - Google Patents

Abstract

Anthraquinone dyes capable of being chromed are prepared by reacting a 4-halogen substituted 1-hydroxy, 1-amino-, 1-alkylamino-or 1-arylamino-anthraquinone which (a) contains no sulpho group in the anthraquinone nucleus, with an aromatic amino-o-oxycarboxylic acid or an ester thereof and then sulphonating the products, or with a sulphonated aromatic amino-o-oxycarboxylic acid or an ester thereof; or (b) contains one or more sulpho groups in the anthraquinone nucleus, with either of the reactants specified under (a) and then spitting off these sulpho groups attached to the anthraquinone nucleus by heating the product with an alkaline solution of hydrosulphite or with dilute sulphuric acid. A modification comprises sulphonation of the condensation product of a leuco quinizarin with an aromatic amino-o-oxycarboxylic acid or an ester thereof and oxidation of the product. The dyes may be after-chromed on the fibre or converted into chromium lakes which may then be applied to the fibre giving in both cases fast grey to green dyeings. In examples: (1) leuco quinizarin is condensed with 5- and 3-amino-2-oxybenzoic acid methyl esters, the respective products saponified while air is introduced, and then sulphonated with monohydrate in presence of boric acid; (2) 4-chlor-1-hydroxyanthraquinone is condensed with 5- and 3-amino-2-oxybenzoic acids and the respective products sulphonated, or with 5- and 3-amino-2-oxy-5-sulphobenzoic acids respectively; (3) 1-amino-4-chloranthraquinone is condensed with 5- and 3-amino-2-oxybenzoic acids and the respective products sulphonated with monohydrate; (4) 1-methylamino-4-bromanthraquinone is condensed with 5- and 3-amino-2-oxybenzoic acids and the respective products sulphonated with monohydrate, or with 5-amino-2-oxy-3-sulphobenzoic acid; 1-ethylamino-4-bromanthraquinone is similarly condensed with 5-amino-2-oxybenzoic acid and the product sulphonated; (5) 1-dichloranilido-4-chloranthraquinone derived by chlorination of the anilido body, is condensed with 3-amino-2-oxybenzoic acid and the product sulphonated; (6) 1-oxy-4-bromanthraquinone-2-sulphonic acid is condensed with 5- and 3-amino-2-oxybenzoic acids or with 5-amino-3-sulpho- and 3-amino-5-sulpho-2-oxybenzoic acids respectively, the b -sulpho group in the anthraquinone residue is eliminated by the action of alkali hydrosulphite, and then in the case of the first two products a sulphonation treatment follows; (7) 1-amino-4-bromanthraquinone-2-sulphonic acid is condensed in the same way as in (6) instead of 1-oxy-4-bromanthraquinone-2-sulphonic acid; (8) 1-oxy-4-bromanthraquinone-2-sulphonic acid is condensed with p-aminobenzoyl - 1 - amino - 2 - oxy - 5 - sulphobenzene -3-carboxylic acid and 4-amino-3<1>-carboxy-4<1>-oxy-5<1> -methyldiphenylmethane respectively, the b -sulpho group eliminated by treatment with alkali hydrosulphite, and in the case of the latter product a sulphonation treatment follows.