GB825377A - New water-insoluble mono azo triazine dyestuffs and processes for their manufacture - Google Patents

Abstract

The invention comprises dyestuffs of formula <FORM:0825377/IV(c)/1> where R is H or a hydrocarbon radicle which may be substituted, X is halogen and Y is sub-stituted or unsubstituted alkyl or aryl, hydroxyl, amino or a radicle containing an N, O or S atom through which it is linked to the triazine ring and the rings P and Q may be substituted except that P, Q, R and Y are free from sulpho, sulphato or carboxy groups. Methyl, ethyl and phenyl radicles are specified for R. Specified substituents for R and Y when alkyl are OH, MeO, CN and F and when aryl are Me, MeO, Cl and Br. X is specified as Cl and Br, and as organic radicles containing the N, O or S bridge MeO, EtO, phenoxy, b -hydroxy-, -carbethoxy-and -cyano-ethyl, methyl-, dimethyl-, cyclo-hexyl- and phenyl-amino and methylmercapto. The dyestuffs may be made by condensing equimolar quantities of appropriate azo compounds and triazines, preferably in a liquid medium such as acetone, at 30-50 DEG C. in the presence of an acid-binding agent. Those dyestuffs which do not contain alkyl or aryl groups attached to a carbon atom of the triazine ring may be made by reacting a compound of formula <FORM:0825377/IV(c)/2> with a compound of formula HZ, where P, Q, R and X are as before and Z is OH, an amino group or an appropriate organic radicle containing an N, O or S link to H. Specified triazines are 2,4-dichloro-6-phenoxy-, -methoxy-, -di-methylamino -, - phenylamino -, - b -cyanethylamino-, -methyl- and -phenyl-1,3,5-triazines. Specified azo compounds are 4-amino-21-hydroxy - 51 - methyl - and - phenyl -, 4 - amino-21,4 - dihydroxy - and 4 - amino - 2 - methoxy-21 - hydroxy - 51 - tert. amyl - azo - benzenes. The products are used in the dispersed dyeing of polyamide, polyurethane, wool, silk and cellulose ester fibres, yellow to orange shades being obtained. Dyestuffs containing a suitable amino group may be diazotized on the fibre and coupled with a component such as 2-hydroxy-3-naphthoic acid to yield navy or black dyeings. Examples are provided illustrating the preparation of the dyestuffs by the methods outlined above and their use in dyeing processes the reactants used being chosen from those indicated above, additional values for Y being phenyl and N-ethyl- and -methylglucamylamino- and N,N-di-b -hydroxyethylamino. The Provisional Specifications describe the preparation of dyestuffs of formula <FORM:0825377/IV(c)/3> where A is the residue of an aromatic azo compound free from sulphonic or carboxylic acid groups and R, X and Y are as above and their use in dyeing processes. Many dyestuffs corresponding to A and not listed in the Complete Specification are specified and the products may contain more than one triazine residue or azo group. The amine group linked to the triazine nucleus may be attached directly or via a chain of atoms, e.g. an alkylene group, which need not all be carbon atoms, to the nucleus of the azo compound. Specification 418,667 is referred to.