GB488863A - Improvements in the manufacture and production of compounds of the anthraquinone series - Google Patents

Abstract

Dyes are made by reacting amines of the formula <FORM:0488863/IV/1> (in which R1 is an alkyl radicle of at least 3 carbon atoms containing at least two hydroxyl groups and R2 is hydrogen, alkyl, aralkyl, or aryl) with bodies of the formula <FORM:0488863/IV/2> (in which A is an anthraquinone radicle, X is a primary or secondary amino group, an arylsulphamido group, a nitro group or a halogen atom in a -position, n is a whole number and Y is a carboxylic or sulphonic halide or ester group), followed if the radicle Y only has reacted either by hydrolyzing at least one of any arylsulphamido groups which may be present to amino groups or reducing at least one of any nitro groups which may be present to an amino group or by converting at least one of any halogen atoms which may be present to amino groups by reaction with ammonia or an amine, the latter step being optional if an amino group was originally present in a -position. Amines specified are 1-amino-2.3-dihydroxypropane, glucamine, and alkylglucamines, and anthraquinones specified are 1-nitro or chlor- or amino-anthraquinone-2-carboxylic acid chloride, 1 - amino - 4 - nitroanthraquinone - 2 - carboxylic acid chloride, 1-amino-4-p-toluenesulphamidoanthraquinone-2-carboxylic acid chloride, 1.4-dichloranthraquinone-6-carboxylic acid chloride, 1.4-di-p-toluenesulphamido-anthraquinone-6 carboxylic acid chloride, 1-iodoanthraquinone-2-sulphonic acid chloride, 1.4-dichloranthraquinone-2 (or 6)-sulphonic acid chloride, and 1.5-diaminoanthraquinone-2.6-dicarboxylic acid chloride. The reaction is carried out in presence of a diluent such as water, an alcohol, pyridine or an excess of the amine. The products dye cellulose esters or ethers and dye acetate artificial silk red or violet shades. In examples: (1) 1-aminoanthraquinone-2-carboxylic acid chloride is boiled in water with methylglucamine or 1-amino-2.3-propane-diol to give the corresponding acid amide; (2) 1-nitroanthraquinone-2-carboxylic acid chloride is reacted with 1-amino-2.3-propane-diol to give 1 - propane - diol - aminoanthraquinone - 2 - carboxylic acid propane-diol-amide; (3) 1-amino4-nitroanthraquinone-2-carboxylic acid chloride is reacted with 1-amino-2.3-propane-diol to give the propane-diol-amide, after which the nitro group may be reduced with sodium sulphide or by vatting; alternatively, 1-amino-4-p-toluenesulphamido - anthraquinone - 2 - carboxylic acid chloride may be reacted with 1-amino-2.3-propane-diol, followed by hydrolysis of the p-toluenesulphamido radical; (4) 1-amino-4-hydroxyanthraquinone - 2 - carboxylic acid chloride is reacted with 1-amino-2.3-propane-diol to give the amide; (5) 1.4-dichloranthraquinone-6-sulphonic or carboxylic acid chloride is reacted with 1-amino-2.3-propane-diol; (6) 1-nitroanthraquinone-2-carboxylic acid methyl ester is reacted in butanol with 1-amino-2.3-propanediol to give the same product as in (2)