Patent GB-439570-A (GB)
Title: The manufacture of new vat dyestuffs
IPC: C09B1/44
Filed: 1934-06-01
Abstract: Vat dyes are prepared by condensing a -aminoanthraquinones with halides of arylenethiazole or oxazole mono- or dicarboxylic acids corresponding to the formula <FORM:0439570/IV/1> wherein X stands for S or O, n for 1 or 2 and the arylene and anthraquinonyl radicles may contain further substituents. Alternatively, a -halogenanthraquinones are condensed with amides of the above acids.  These acids are prepared by condensing anthraquinone aldehydes with o-aminomercapto- or o-amino-hydroxyarylene carboxylic acids.  In examples: (1) 2 - (2<1> - anthraquinonyl) - benzthiazole - 6-carboxylic acid chloride (this acid is prepared by treating p-aminobenzoic acid with disulphurdichloride (cf. Specification 17417/14, [Class 2 (iii)], saponifying according to Specification 306,590, [Class 2 (iii)], and condensing the product with anthraquinone-2-aldehyde in concentrated sulphuric acid or in a high-boiling solvent in presence of sodium carbonate) is condensed with 1-aminoanthraquinone (dyes yellow), 1-amino-4- or 5-benzoylaminoanthraquinone (yellow to orange shades), 1-amino-4-acetylaminoanthraquinone (orange shades), 1.5-diaminoanthraquinone (yellow shades); (2) 2-(2<1>-anthraquinonyl)-6-chlorbenzothiazole-4-carboxylic acid chloride (this acid is derived as indicated in (1) starting from anthranilic acid) is condensed with 1-aminoanthraquinone (yellow shades), 1-amino-4- or 5-benzoylaminoanthraquinone (reddish-violet to reddish-brown shades); (3) 2-(1<1>-amino-2<1>-anthraquinonyl-) -benzthiazole-6-carboxylic acid chloride is condensed with 1-aminoanthraquinone (red shades), 1 - amino - 5 - benzoylaminoanthraquinone (reddish-brown), 1.4- or 1.5-diaminoanthraquinone (reddish-violet to bluish-red); (4) 2-(1<1>-amino-2<1>-anthraquinonyl) -6-chlorbenzthiazole-4-carboxylic acid chloride is condensed with 1-amino-4- or 5-benzoylaminoanthraquinone (reddish-violet to reddish-brown); (5) 2 - (2<1> - anthraquinonyl) - benzthiazole - 4.6-dicarboxylic acid dichloride (prepared as in (1) from 1-amino-2.4-isophthalic acid) is condensed with 1-aminoanthraquinone (yellow), 1-amino-5-benzoylaminoanthraquinone (reddish-yellow); (6) 2 - (1<1> - amino - 2<1> - anthraquinonyl) - benzthiazole-4.6-dicarboxylic acid dichloride is condensed with 1-aminoanthraquinone (bluish-red); (7) 2 - (2<1> - anthraquinonyl) - benzoxazole - 5-carboxylic acid chloride (derived from 1-amino-2-oxy-5-benzoic acid and anthraquinone-2-aldehyde) is condensed with 1-aminoanthraquinone (yellow), 1-amino-4- or 5-benzoylaminoanthraquinone (orange to yellow), 1.5-diaminoanthraquinone (yellow); (8) 2 - (2<1> - anthraquinonyl) - 4.5 - benzobenzoxazole - 7 - carboxylic acid chloride (derived from anthraquinone-2-aldehyde and 1-amino-2-oxynaphthalene-3-carboxylic acid) is condensed with 1-aminoanthraquinone (yellow), 1-amino-4- or 5-benzoylaminoanthraquinone (orange to yellow); (9) 2-(1<1>-amino - 2<1> - anthraquinonyl) - 4.5 - benzobenzoxazole-7-carboxylic acid chloride (prepared by condensing 1 - aminoanthraquinone - 2 - aldehyde with 1 - amino - 2 - oxynaphthalene - 3 - carboxylic acid) is condensed with 1-aminoanthraquinone (bluish-red), 1 - amino - 5 - benzoylaminoanthraquinone.  In two cases the above product are also prepared by reacting the acid amide with the appropriate a -halogenanthraquinone.  The products have better solubility in the vat than those of Specification 417,980.