GB929097A - New monoazo dyes containing hydrazinyl substituted triazine residues - Google Patents

Abstract

2-(4,6-Dihydrazino-1,3,5-triazinyl-2)- and 2-[4,6- di(phenylhydrazino)- 1,3,5-triazinyl- 2) -amino- 5-hydroxynaphthalene- 7-sulphonic acids are prepared by condensing cyanuric chloride with an equimolar amount of 2-amino-5-naphthol-7-sulphonic and then reacting the primary condensate with 2 molar proportions of hydrazine or phenylhydrazine. Specifications 842,802 and 872,249 are referred to.ALSO:The invention comprises monoazo dyes which contain attached by way of an amino group at least one group of formula:- <FORM:0929097/IV(a)/1> wherein X is the radical of hydrazine or a substituted hydrazine and Y is a halogen atom, an amino group, a hydroxyl group, a mercapto group, the radical of hydrazine or a substituted hydrazine, or an aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical attached by way of an oxygen, sulphur or nitrogen atom to the triazine ring. The dyes are prepared by reacting a trihalo-s-triazine in any sequence with (a) a monoazo dye or an intermediate of such a dye containing a primary or secondary amino group and (b) hydrazine or a substituted hydrazine to form a secondary condensation product, if desired exchanging the final halogen atom by treatment with alkali, ammonia, an amine, alcohol, phenol or mercaptan or hydrazine or hydrazine derivative and when an intermediate has been used converting this into the dye by coupling. The dyes may be treated with formaldehyde to prepare the corresponding methylol compounds as described in Specifications 842,802 and 872,249 and the methylol compounds may also be etherified or esterified. Specified substituted hydrazines include methylhydrazine, N1,N-dimethylhydrazine, acetylhydrazine, phenylhydrazine and its sulphonic acids, maleic acid hydrazide, N-aminoethylurethane, 2,4,6-trihydrazino-1,3,5-triazine, aminoguanidine, hydrazo-dicarboxylic acid amide, pyrazoline, N-aminopiperazine and the compound of formula <FORM:0929097/IV(a)/2> The dyes may be used to colour natural and synthetic polyamide fibres, leather, paper and, preferably, cellulose. The dyeings may be carried out in the presence of acid substances and hardenable aminoplast-forming substances, possibly together with an aldehyde or a substance yielding an aldehyde, and fixed by a heat treatment. In examples: (1) the monoazo dye 1-aminobenzene-2-sulphonic acid--->2-(8 -hydroxy - 3,6 - disulphonaphthyl - 1 - amino) -4,6-dichloro-s-triazine is reacted with an equimolar amount of hydrazine hydrate; (2) cotton fabric is padded with an aqueous solution containing the dye obtained in (1), 1,3-dimethylol -5-methylperhydrotriazone-(2) and monoammonium phosphate, squeezed out, dried and heated at 145 DEG C. for 8 minutes; (3) a cotton fabric which has been treated with a caustic soda solution is padded with a liquor containing a dyestuff, methylol or methylene ether, the tetramethyl ether of tetramethylolmelamine, the ammonium salt of polyacrylic acid, polyglycol ether, sodium isopropylnaphthalene sulphonate and a mixture of diethanolamine and triethanolamine hydrochlorides, squeezed out and dried and heated on flat frames at 145 DEG C. A dyed crease resistant fabric is obtained. Further examples of the dyes are specified.