Patent GB-580174-A (GB)
Title: A process for producing fast dyeings on cellulose fibres
IPC: C09B33/02
Filed: 1943-03-18
Abstract: Textiles consisting of or containing cellulose fibres, e.g textiles of natural or regenerated cellulose or mixed textiles such as mixtures of wool and viscose staple fibres, are dyed by forming thereon a copper compound of an azodyestuff from two molecular proportions of a diazotized 1 - amino - 4 - aroylaminobenzene - 2 - carboxylic acid with one of a pyrazolone derivative of the general formula <FORM:0580174/IV/1> in which both symbols Py represent the pyrazolone nuclei of a 1-phenyl-5-pyrazolone and x represents a bridge consisting of a -CO-group or the residue of a heterocyclic compound containing at least two reactive halogen atoms, such as cyanuric chloride, 2 : 4 : 6-tribromopyrimidine, 2 : 6-dichloro-4-methylpyrimidine or 2 : 4-dichloroquinazoline, in which the two halogen atoms have been exchanged for the <FORM:0580174/IV/2> groups.  In an example, cotton is dyed with the dyestuffs from diazotized 1-amino-4-benzoylaminobenzene - 2 - carboxylic acid and pyrazolones of the above formula in which each Py is a 3-methyl-5-pyrazolone residue and x is -CO- or the grouping <FORM:0580174/IV/3> and is then treated in the same bath with a solution of copper sulphate and tartaric acid neutralized with caustic soda. Specification 503,609 is referred to.  The Specification as open to inspection under Sect. 91 comprises also the manufacture of azo-dyestuffs by coupling a pyrazolone of the general formula <FORM:0580174/IV/4> (in which Py represents the pyrazolone nucleus of a 1-aryl-5-pyrazolone and x represents the residue of a 1-aryl-5-pyrazolone or the residue <FORM:0580174/IV/5> where y represents a bridge consisting of the residue of a compound of the type of phosgene or cyanuric chloride having 2 or 3 replaceable halogen atoms) with a diazotized 1-amino-4-acidylaminobenzene - 2 - carboxylic acid, and, if desired, converting the product into a complex copper compound by treatment with an agent yielding copper. Alternatively, 2 molecular proportions of a pyrazolone derivative of the above formula, in which x is an amino group or a group convertible thereto, are reacted in either order with 2 molecular proportions of a diazotized 1 - amino - 4 - acidylaminobenzene - 2 - carboxylic acid and (if necessary after converting the group x into an amino group) with 1 molecular proportion of a compound of the type of phosgene or cyanuric chloride having 2 or 3 replaceable halogen atoms, the third halogen atom (if present) being, if desired, subsequently exchanged by reaction with compounds capable of reacting therewith, such as ammonia, primary amines (e.g. monomethylamine, monoethanolamine, aniline or 1-amino-4-hydroxybenzene-3-carboxylic acid), or secondary amines (e.g. monomethylaniline).  The residue Py may be that of 5-pyrazolone itself or its 3-methyl, aryl or carboxy derivatives, the bridge y may be (in addition to the residues specified for x in the Specification as accepted) the residues of cyanuric bromide or 1 : 3-dichloro-5-phenyl- or 5-methyl-triazine, and the acidyl residue in the diazo-component may be derived from acetic, monochloracetic, benzoic, 4-chlorobenzoic, 3-sulphobenzoic, phthalic, phenylacetic, phenoxyacetic or oxalic acid.  Examples are given of both methods of preparing the dyestuffs.  This subject-matter does not appear in the Specification as accepted.