GB845220A - Improvements in or relating to water-insoluble tertiary amines - Google Patents

Abstract

The invention comprises water-insoluble tertiary amines of formula: <FORM:0845220/IV(b)/1> p wherein x and y are a hydrogen or halogen atom or an alkyl or alkoxy group, y may also be a trifluoro-methyl or -acetylamino group or an alkanoylamino group with not more than 18 carbon atoms, n is 1 or 2, R1 is an alkylene group with 1-4 carbon atoms, R2 is an alkylene group with 2-4 carbon atoms, R3 is an aliphatic, cycloaliphatic or aromatic radical which is free from sulphonic acid or sulphonamide groups and may be further substituted, Z is -O- or -NH- and M is a hydrogen or halogen atom, a methoxy, ethoxy, cyano difluoromethyl trifluoromethyl, carboalkoxy or a <FORM:0845220/IV(b)/2> Group when n is 1, or a single linkage directly joining one R1 to the other R1 when n is 2. They are prepared by reacting 1 mol of a compound of formula: <FORM:0845220/IV(b)/3> with 1 or 2 mols of an isocyanate of formula O=C=N-R3 wherein x, y, n, Z, R1, R2 and R3 are as defined above and Q is a hydrogen or halogen atom or a hydroxy, amino, methoxy, ethoxy, difluoromethyl, trifluoromethyl, cyano or carboalkoxy group when n is 1 and a single linkage directly joining one R1 to the other R1 when n is 2. They are used in the preparation of styryl and azo dyestuffs (Cf. Specifications 824,443, 843,643 and 843,644). In Examples: (1) ethyl isocyanate is reacted, by refluxing in dry benzene, with 1-(N-ethyl-N-b -hydroxyethyl)amino-3-methylbenzene to give the corresponding ethyl carbamic acid ester; (2) the amine specified in (1) and phenyl isocyanate are fused together to give the corresponding phenyl carbamic acid ester; (3) phenyl isocyanate is dropped into the stirred melt of N:N1-diphenyl-N:N1-dihydroxyethyl-ethylenediamine to give the corresponding bis-phenyl carbamic acid ester. The preparation of many similar compounds is specified in tables.ALSO:Azo dyes are specified derived from coupling components of formula: <FORM:0845220/IV (c)/1> wherein x and y are a hydrogen or halogen atom or an alkyl or alkoxy group, y may also be a trifluoromethyl or -acetylamino group or an alkanoylamino group with not more than 18 carbon atoms, n is 1 or 2, R1 is an alkylene group of 1-4 carbon atoms, R2 is an alkylene group of 2-4 carbon atoms, R3 is an aliphatic, cycloaliphatic or aromatic radical which is free from sulphonic acid or sulphonamide groups and may be further substituted, Z is -O- or -NH- and M is a hydrogen or halogen atom, a methoxy, ethoxy, cyano, di- or tri-fluoromethyl carboalkoxy, or <FORM:0845220/IV (c)/2> group when n is 1, or a single linkage directly joining one R1 to the other R1 when n is 2. Dyes obtained by coupling compounds of the above formula with diazotised 4-nitroaniline when n is 1 and diazotised 4-methylsulphonyl -2- chloroaniline when n is 2 are specified. Specifications 824,443, 843,643 and 843,644 are referred to.