Patent GB-298545-A (GB)
Title: Improvements in the manufacture and production of vat dyestuffs of the anthraquinoneseries
IPC: C09B5/24
Filed: 1927-06-07
Abstract: 298,545. Johnson, J. Y., (I. G. Farbenindustrie Akt.-Ges.). June 7, 1927. Á - Anthraquinonylanthraquinoneoxazoles are prepared by condensation of o-aminohydroxyanthraquinones with ,anthraquinone aldehydes or compounds capable of furnishing the same, such as azomethines of anthraquinone aldehydes, or #-dichlormethyl anthraquinones, or by condensation of the anthraquinonyl amides of anthraquinone carboxylic acids substituted in the oposition to the amino group by hydroxyl or a negative substituent, or of components furnishing the same as for example an anthraquinone isoxazole and an aminoanthraquinone. Either of the anthraquinone residues may contain additional substituent. Those products which contain at least one free amino group may be converted into dyes of considerably deeper colour by treatment with oleum, with or without addition of catalysts such as sulphur or iodine; the resulting compounds change colour under the influence of alkalies, but may be freed from this defect by alkylation in the usual manner, e.g. with p-toluene sulphonic acid methyl ester. In examples :-(1) 2 : 3-aminohydroxyanthraquinone is condensed with anthraquinone-2-aldehyde; the product dyes cotton light yellow; (2) 2-amino- 1-hydroxyanthraquinone is condensed with the azomethine derived from 1-aminoanthraquinone-2-aldehyde and aniline to a blue-red vat dye; (3) 3-aminoalizarine is condensed with 1-aminoanthraquinone-2-aldehyde to a vat dye giving red shades on cotton; (4) 1-amino-2-hydroxyanthraquinone is condensed with 1-aminoanthraquinone- 2-carboxylic chloride to a red vat dye; (5) the acylaminoanthraquinone prepared from 1 : 3-dibrom-2-aminoanthraquinone and anthraquinone-2- carboxylic acid is condensed to a product which dyes cotton light yellow from the vat; (6) the condensation product from 2 : 3-bromaminoanthraquinone and 1-aminoanthraquinone-2-carboxylic chloride is further condensed to a bluish red vat dye; (7) antraquinone 1 (N) : 2-isoxazole is condensed with 2' : 3-aminohydroxyanthraquinone to obtain the same product as in example 6; (8) 1-aminoanthraquinone-2-carboxylic acid is treated with thionyl chloride in nitrobenzene ,and subsequently with 2 : 3,aminohydroxyanthraquinone, in the presence of nitrobenzene and ptoluene sulphonic acid, to give the same product as in example 6; (9) 1-aminoanthraquinone-2- carboxylic acid is treated with thionyl chloride, in nitrobenzene, and then 2 : 3-aminohydroxyanthraquinone and an alkali added and the reaction completed, to give the same product as in example 6: (10) the dyestuff obtainable in the above manner from 1-aminoanthraquinone-2-aldehyde and 2 : 3-aminohydroxyanthraquinone is treated with 75 per cent oleum at room temperature to give a blue vat dyestuff, which after methylation with methyl p-toluenesulphonate gives violet shades; (11) the dyestuff obtained according to example 4 is then treated with 50 per cent oleum and a little iodine at room temperature to give a blue vat dye; methylation of this gives a violet dye; (12) the dyestuff prepared in the above manner from o-diamino anthraflavic acid obtained by nitrating anthraflavic acid and reducing the product) and 1-aminoanthraquinone-2- aldehyde, which gives blue red dyeings, is treated with 65 per cent oleum at 50‹ C. to give a dark blue vat dye. 2 : 3-Aminohydroxythraquinone is prepared by treating 2 : 3-bromhydroxyanthraquinone with concentrated ammonia at 130‹ C. Acidylaminoanthraquinones.-The condensation products from anthraquinone-2-carboxylic chloride and 2-amino-1. : 3-dibrom-anthraquinone, and from 1-aminoanthraquinone-2-carboxylic chloride and 2 : 3-bromaminoanthraquinone, are mentioned. Specification 147,001 is referred to.