GB948007A - New dyestuff derivatives and process for their manufacture - Google Patents

Abstract

948,007. Synthetic resin derivatives of dyestuffs. CIBA Ltd. May 5, 1960 [May 6, 1959; July 13, 1959], No. 16001/60. Heading C3R. [Also in Division D1] A process for the manufacture of new dyestuffs derivatives comprises reacting an azo dyestuff, which is free from any acid water-solubilizing group and contains at least one substituent capable of reacting with alkylol groups or etherified alkylol groups, with a mixture capable of giving rise to a melamine or urea-formaldehyde resin precondensate containing alkylol groups which may be etherified. Suitable dyestuffs contain -NH 2 or N-alkylol groups as the reactive substituents, which may be bound to benzene or naphthalene residues. The dyestuffs may contain a residue of the formula: in which X represents a substituted amino or hydroxyl group, an alkyl, aryl or aralkyl radical, a halogen atom or an : group and m and n each=1 or 2, or a residue of the formula: The -NH 2 group may also be present in H 2 N.CO.CH 2 , urea or -SO 2 NH 2 groupings. Preferred dyestuffs are monoazo dyestuffs which may also contain a metal especially copper, chromium or cobalt, bound in complex union. The azo linkage may be bound to a benzene nucleus and to a naphthalene or pyrazolone residue. In the reaction with the resin components the dyestuffs are advantageously used as micro-dispersions of particle size 1 to 10Á. Etherification of the product can be effected after the dyestuff derivative has been made, or the dyestuff itself can be reacted with a resin precondensate containing etherified alkylol groups. The products can be made up as dispersions for dyeing or printing. There may be added acid catalysts, such as ammonium sulphate, nitrate, phosphate or silicofluoride, magnesium chloride, zinc nitrale, zinc fluoroborate, tartaric or formic acid or a hydrochloride of an organic base; polymers of ethylenic compounds; and thickeners such as starch, tragacanth, British gum or urea. In Example (1) the dyestuff is prepared by coupling diazotized 1-amino-4-methoxy benzene 1 -acetylamino-4-hydroxybenzene, hydrolysing reacting with cyanurie chloride and then replacing one of the chlorine atoms attached to the triazine ring by -NH, by reaction with ammonia. The dyestuff is reacted with aqueous formaldehyde and melamine in a solution kept at pH 8 to 8À5 by the addition of ammonia. It is then etherified with butanol in the presence of formic 'acid. The product is dispersed in water with a reaction product of 200 mols of ethylene oxide and 1 mol of hydroabietyl alcohol, cross-linked with 1% hexamethylene diisocyanate. In Example (5) a pigment of the formula: is reacted with an aqueous mixture of urea and formaldehyde containing sodium hydroxide solution. A number of other dyestuffs are specified.