GB381942A - Manufacture of new anthraquinone derivatives - Google Patents

Abstract

Anthraquinone derivatives are prepared by reacting a 1-acylamino-3-halogenanthraquinone with a compound containing at least one replaceable atom of hydrogen or a metal attached to nitrogen, oxygen or sulphur, the process of Specification 381,920 being excluded. Reaction takes place with elimination of the 3-halogen atom to give dyestuffs. The properties of these products may be modified by further treatment with an acid condensing agent. Substances suitable for the initial condensation comprise ammonia, an alcoholate, a phenolate, a xanthate, a mercaptan, a thiophenol, a sulphamide, a primary or secondary amine of the aliphatic or aromatic series, or of a condensed ring system such as an aminoanthraquinone, an aminopyranthrone, an aminoanthanthrone or an aminodibenzanthrone. The condensation is preferably carried out in presence of a diluent, an acid-binding agent and a catalyst. In examples: (1) 1-benzoylamino-3-bromanthraquinone (prepared by benzoylating the 1-amino-3-bromoanthraquinone) is condensed with (i) phenol (dyes greenish-yellow); (ii) p-toluidine (dyes bright red shades); (iii) 1-aminoanthraquinone (dyes brick-red); (iv) 1 : 4-aminomethoxyanthraquinone (dyes bordeaux tints); (v) 1 : 5-monobenzoyldiaminoanthraquinone (dyes brownish-red); on treatment with chlorsulphonic acid an orange dyeing product is obtained; (vi) 1 : 8-monobenzoyldiaminoanthraquinone (dyes brownish-red); (vii) 1 : 5-diaminoanthraquinone (\ba1/2\be mol.) (dyes bordeaux shades); (viii) 1 : 4 - monobenzoyldiaminoanthraquinone and the anthramide treated with chlorsulphonic or sulphuric acid (dyes brown); (ix) p-toluenesulphonamide, hydrolysis by means of concentrated sulphuric acid gives a new compound, apparently 1 - benzoylamino - 3 - aminoanthraquinone, which under more drastic conditions yields 1 : 3-diaminoanthraquinone; (x) thiophenol-o-carboxylic acid; (xi) 4-amino-4<1>-chloro-2 : 1 - anthraquinone - thioxanthone (prepared by reacting 1-chloro-4-aminoanthraquinone with 3-chloro-1-thiophenol - 6 - carboxylic acid and condensing the product with chlorsulphonic acid) (dyes grey); (xii) 5-amino-2 : 1-anthraquinone-benzacridone (prepared by reacting the urethane of 1-chloro-5-aminoanthraquinone with anthranilic acid and saponifying prior to ring-closure with chlorosulphonic acid) (dyes violet-brown); (xiii) monoaminopyranthrone (prepared by reducing the mononitro derivative obtained by the action of concentrated nitric acid in nitrobenzene) (dyes black-olive); (xiv) monaminodibenzanthrone (Specification 1818/05, [Class 2, Acids and salts, Organic &c.], (dyes dark green); (xv) 5 : 5<1>-diamino-1 : 1<1>-anthramidocarbazole (dyes red-brown); (2) 1-benzoylamino-3 - chloranthraquinone is condensed with 1 : 4-aminomethoxyanthraquinone as in (iv) above; (3) 1-acetylamino-3-bromanthraquinone is condensed with 1 : 5-diaminoanthraquinone (\ba1/2\be mol.) (dyes bordeaux red). An example of the dyeing of cotton goods is also given. Specification 25986/09, [Class 2 (iii), Dyes &c.], also is referred to.