GB1033266A — Improvements relating to mono-and dis-azo dispersion dyestuffs and their use

USPTO Abstract

The invention comprises azo dyes, free from water-solubilizing groups which dissociate acid in neutral water, of formula <FORM:1033266/C4-C5/1> wherein A is the radical of an aromatic carbocyclic diazonium compound which may be substituted by a phenylazo group or of an aromatic heterocyclic diazonium compound, R1 and R2 are inert monovalent substituents and R3 is a hydrocarbon radical or a carboxylic acid ester or amide group. The dyes are prepared by coupling an appropriate diazonium compound with a 1-[41,61-di-substituted-triazinyl - (21)] - 3 - substituted - 5 - pyrazolone (see Division C2). The dyes may be used to colour synthetic textile fibres such as polyamides and particularly polyesters in yellow and red shades.ALSO:Compounds of formula <FORM:1033266/C2/1> wherein R1 and R2 are inert substituents and R3 is a hydrocarbon radical or a carboxylic acid ester or amide group and their preparation are described. They are used as intermediates in the preparation of azo dyes (see Division C4). The compounds are prepared by condensing b -ketocarboxylic acid acid derivatives with S-triazinyl-(2)-hydrazines. In an example 1-[41,61 - bis - ethylamino - triazinyl - (21)] -3- methyl-5-pyrazolone is prepared by condensing 2,4 - bis - ethylamino - 6 - hydrazino - triazine with acetoacetic acid methyl ester. Also specified are 1-[41,61-bis-methylamino- or -iso- or -n-propylamino- or -n-butylamino-triazinyl-(21)] - 3 - methyl - 5 - pyrazolone, 1 - [41 -phenyl-amino - 61 - ethylamino - triazinyl - (21)] - 3-methyl - 5 - pyrazolone, 1 - [41 - benzylamino-61 - methylamino - triazinyl - (21)] - 3 - methyl-5-pyrazolone, 1 - [41 - cyclohexylamino - 61 - n-propylamino - triazinyl - (21)] - 3 - methyl - 5-pyrazolone, 1 - [41,61 - bis - aminotriazinyl-(21)] - 3 - methyl - 5 - pyrazolone, 1 - [41,61-bis-dimethyl- or -diethyl- or -di-n-butyl-amino-triazinyl - (21)] - 3 - methyl - 5 - pyrazolone, 1 - [41,61 - bisethylamino - triazinyl - (21)] - 3-butyl - 5 - pyrazolone, 1 - [41 - (211 - methylphenyl) - amino - 61 - diethylamino - triazinyl-(21)] - 3 - methyl - 5 - pyrazolone, 1 - [41 - n-propyl - amino - 61 - diethylamino - triazinyl-(21)] - 3 - methyl - 5 - pyrazolone, 1 - [41, 61-bis-ethylamino- or -diethylamino- or -methylamino - triazinyl - (21)] - 3 - ethoxycarbonyl - 5-pyrazolone, 1 - [41,61 - bis - n - butylamino- or -ethylamino - triazinyl - (21)] - 3 - methoxy-carbonyl - 5 - pyrazolone, 1 - [41,61 - bis -methoxypropylamino- or -bis - N - methyl - N - b -hydroxyethyl - amino - triazinyl - (21)] - 3-methyl - 5 - pyrazolone, 1 - [41 - tert. - butyl-amino - 6 - N - methyl - N - hydroxyethylamino-triazinyl - (21)] - 3 - methyl - 5 - pyrazolone, 1 - [41 - hydroxy - 61 - sec - butylamino- or -diethylamino - triazinyl - (21)] - 3 - methyl - 5-pyrazolone, 1 - [41 - phenylamino - 61 - hydroxy-ethylamino - triazinyl - (21)] - 3 - methyl - 5-pyrazolone, 1 - [41,61 - bis - N - methyl - N -b -hydroxy - ethylamino - triazinyl - (21)] - 3-phenyl - pyrazolone, 1 - [41,61 - bis - di -b -hydroxyethylamino - triazinyl - (21)] - 3-methyl - 5 - pyrazolone, 1 - [41 - b - methoxy-ethoxy - 6 - ethylamino - triazinyl - (21)]- or -[41 - ethoxy - 61 - n - propylamino - triazinyl-(21)]- or -[41 - methoxy - 61 - diethylamino-triazinyl - (21)]- or -[41 - methoxy - 61 - benzyl-amino - triazinyl - (21)] - 3 - methyl - 5 - pyrazolone, 1 - [41,61 - bis - methylamino - triazinyl-(21)] - 3 - carbamyl - 5 - pyrazolone, 1 - [41,61-bis - ethylamino - triazinyl - (21)] - 3 - N-methyl- or N,N - dimethyl - carbamyl - 5-pyrazolone, 1 - [41,61 - bis - ethoxy- or -isopropyloxy - triazinyl - (21)] - 3 - methyl - 5-pyrazolone, 1 - [41,61 - bis - ethoxy - triazinyl-(21)] - 3 - methyl- or -butyl - 5 - pyrazolone, 1 - [41,61 - bis - n - butyloxy - triazinyl - (21)]-3 - ethyl - 5 - pyrazolone, 1 - [41,61 - bis -piperidino- or -morpholino - triazinyl - (21)]-3 - methyl - 5 - pyrazolone, 1 - [41,61 - bis-methoxyo n - butyloxy - triazinyl - (21)]-3 - methyl - 5 - pyrazolone and 1 - [41 - ethoxy-61 - (411 - chlorophenyl) - amino - triazinyl-(21)]-3-methyl-5-pyrazolone.