GB921250A - New dyes of the tetrazaporphin series - Google Patents

Abstract

The invention comprises water-soluble or insoluble tetrazaporphin dyes which contain attached via an amino group, at least one group of the formula <FORM:0921250/IV(a)/1> where X is a hydrazine or an alkyl or acyl substituted hydrazine group and Y is chlorine, bromine, hydroxyl, mercapto, sulphonic acid, a primary, secondary or tertiary amino group, an ether or thioether group or a hydrazine or substituted hydrazine group. The dyes are made by condensing at temperatures of up to 40 DEG C. one mole of cyanuric chloride or bromide in either order with one mole of a tetrazaporphin dye containing at least one primary or secondary amino group and one mole of hydrazine or an alkyl or acyl hydrazine, the remaining halogen atom on the triazine ring if desired being replaced by a hydroxyl group by hydrolysis or by a mercapto, sulphonic acid, a primary, secondary or tertiary amino, an ether, thioether, hydrazine or substituted hydrazine group by treatment at temperatures of up to 100 DEG C. with a metal sulphite or sulphide, ammonia, a primary or secondary amine, an alcoholate or mercaptan or hydrazine or a hydrazine derivative. The methylol compounds of the dyes are made by reaction of the above dyes with formaldehyde. Examples are given. The water-soluble dyes dye and print wool, silk or polycaprolactam fibres and dye leather and paper. The methylol compounds of the dyes and the esters and ethers thereof dye and print textile materials of natural or regenerated cellulose, and these or the dyes themselves may be applied together with hardenable amino-plast forming substances or precursers thereof and possibly with aldehydes such as formaldehyde in the presence of acids or acid-reacting compounds such as ammonium chloride and the fabric then subjected to heat treatment. In examples cotton fabric is dyed with an aqueous solution containing one of the above dyes and either (1) 1:3-dimethylol-5-methyl perhydrotriazone-2 and monoammonium phosphate, or (3) dimethylol-dihydroxyethylene urea and ammonium nitrate, and the fabric is then heated. Specification 827,569 is referred to.