GB361423A - Process for the manufacture of new vat dyestuffs - Google Patents

Abstract

Anthraquinone-acridone dyestuffs.--A polyhalogenanthraquinone-2.1 (N)-benzacridone containing at least two halogen atoms in the anthraquinone nucleus and in which the acridone ring may likewise be substituted by halogen, is condensed with two mols. of an aminoanthraquinone or a substitution product thereof. Or an aminoanthraquinone-2.1 (N)-benzacridone containing two amino groups in the anthraquinone nucleus is condensed with two mols. of a halogenanthraquinone or a substitution product thereof. The products, which are dyestuffs, may be carbazolized by treatment with an acid condensing agent. Thus carbazolization may be effected by means of aluminium chloride in conjunction with sodium chloride or with pyridine, or by means of concentrated sulphuric acid or chlorsulphonic acid. The polyhalogenanthraquinone-2.1-benzacridones may be prepared by causing a halogenanthraquinone-2.1-benzacridone containing at least one halogen atom in the 5-, 6-, 7- or 8-position to react in the known manner with chlorine or with chlorinating agents. In examples: (1) 4.8 : Bz 2.4-tetrachloranthraquinone-2.1-benzacridone (prepared by condensing 1 mol. of anthranilic acid with 1 mol. of 1.8-dichloranthraquinone, heating the reaction product with strong sulphuric acid, and chlorinating the resulting acridone in nitrobenzene in the presence of iodine) is condensed with 2 mols. of 1-aminoanthraquinone, and the product heated in pyridine with aluminium chloride; it dyes yellowish-olive shades : (2) 4.5 : Bz 2.4-tetrachloranthraquinone-2.1-benzacridone (prepared by chlorinating 5-chloranthraquinone-2.1-benzacridone in nitrobenzene and in presence of iodine) is treated as in (1) above; the product dyes a reddish-olive shade; if the 1-aminoanthraquinone is replaced by 1-amino-4-benzoylaminoanthraquinone a product dyeing blueish-grey shades is obtained, and which, on carbazolizing by means of (i) concentrated sulphuric acid (whereby only one carbazole ring is formed), yields a violet-brown dye, and (ii) aluminium chloride in pyridine (whereby two carbazole rings are formed), yields a blackish-brown dye: (3) 4.6 : Bz 2.4-tetrachloranthraquinone-2-1 (N)-benzacridone (prepared by condensing 1.6-dichloranthraquinone with anthranilic acid, treating the reaction product with strong sulphuric and chlorinating in nitrobenzene in presence of iodine) is condensed with 2 mols. of 1-benzoylamino-4-aminoanthraquinone; the product dyes grey shades: (4) 4 : 8-diaminoanthraquinone - 2.1 - benzacridone (prepared from anthranilic acid and 1-chloro-4.8-diaminoanthraquinone) is condensed with 2 mols. of 1-chloranthraquinone and the product treated in pyridine with aluminium chloride. Specifications 305,082 and 311,283, [both in Class 2 (iii), Dyes &c.], also are referred to. 1-Chloro-4.8-diaminoanthraquinone is prepared by nitrating 1-chlor-8-nitroanthraquinone and reducing with grape sugar.