GB585730A - Process for the preparation of dyestuffs of the anthraquinone series - Google Patents

Abstract

Acid wool dyestuffs of outstanding shades by artificial light are obtained by condensing anthraquinone derivatives having replaceable substituents in the 1 and 4 positions and substituted by halogen in both the 6 and 7 positions, with polynuclear aromatic or partially hydrogenated aromatic amines and sulphonating the resultant condensation products. Specified anthraquinone derivatives are: 6 : 7-dichloroquinizarine, 6 : 7 - dibromoquinizarine, 6 : 7 - bromochloroquinizarine, 6 : 7 - dichloro - 1 : 4 - hydroxyaminoanthraquinone, 6 : 7 - dichloro - 1 : 4-diaminoanthraquinone or their leuco derivatives or 1 : 4 : 6 : 7-tetrahalogenanthraquinone. Specified polynuclear amines are: a - and b -naphthylamines, 1- and 2-amino-5 : 6 : 7 : 8-tetrahydronaphthalene, 2 - amino - 1 : 2 : 3 : 4 - tetrahydronaphthalene, 1-amino-4-cyclohexyl-benzene, the aminodiphenyls, the amino di-phenylethers and the aminodiphenylmethanes. When the anthraquinone derivative is wholly or partially in the form of its leuco-compound, oxidation may be necessary before sulphonation. In an example, 6 : 7-dichloroquinizarine is condensed with 1-amino-5 : 6 : 7 : 8-tetrahydronaphthalene in the presence of its leuco-compound and of boric acid, with subsequent sulphonation with oleum to produce a dyestuff which dyes wool in yellowish green shades. The 6 : 7-dichloroquinizarine may be replaced by 6 : 7 - dichloro - 1 : 4 - hydroxyamino- or diaminoanthraquinone or the corresponding 6 : 7-dibromo-compounds. Samples have been furnished under Sect. 2 (5) of dyestuffs prepared by condensing 1 : 4 : 6 : 7-tetrachloroanthraquinone with 2 - amino - 5 : 6 : 7 : 8-tetrahydronaphthalene, 6 : 7-dichloroquinizarine in the presence of its leuco compound with 2-amino-5 : 6 : 7 : 8-tetrahydronaphthalene, 2 - amino - 1 : 2 : 3 : 4 - tetrahydronaphthalene, 4 - aminodiphenyl, 4 - aminodiphenylether and a - and b -naphthylamines, with subsequent sulphonation. Specification 466,714 is referred to. The Specification as open to inspection under Sect. 91 also refers to starting materials containing only a single halogen in the 6 or 7 position such as 6-chloroquinizarine, 6-bromoquinizarine, 6-chlor-1 : 4-hydroxyaminoanthraquinone, 6-chlor- and 6-brom-1 : 4-diaminoanthraquinones, and their leuco compounds and also 1 : 4 : 6-trihalogen anthraquinones, and describes the condensation of 6-chloroquinizarine with 1- or 2-amino-5 : 6 : 7 : 8-tetrahydronaphthalene, 2-amino-1 : 2 : 3 : 4-tetrahydronaphthalene, 4-amino - diphenylether, 4-aminodiphenyl and 4-aminodiphenylmethane and of 1 : 4 : 6-trichloranthraquinone with 2-amino-5 : 6 : 7 : 8-tetrahydronaphthalene, with subsequent sulphonation. This subject-matter does not appear in the Specification as accepted.