Patent GB-864292-A (GB)
Title: Production of polymers from olefinically unsaturated monomers containing a naphthol coupling component chemically combined in said polymers
IPC: D01F6/20
Filed: 1959-09-08
Abstract: A method of preparing dyeable polymers from olefinically unsaturated monomers comprises polymerizing the monomers in the presence of naphthol coupling components to form polymers having said coupling components chemically bound to the molecular structures of the polymers in amounts from 0,5 to 6,0% by weight of the polymers. Specified monomers are vinyl acetate, vinyl ethenyl carbinols, methyl vinyl ketone, methyl isopropenyl ketone, methyl vinyl ether, ethylene, propylene, styrene, chlorostyrene, p-methoxystyrene, alpha-methylstyrene, vinyl naph-thalene, acrylic acid, methacrylic acid, acrylonitrile, methacrylamide, methyl acrylate, ethyl acrylate, isobutyl acrylate, methyl-alphachloracrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, diallyl maleate, fumaric acid esters, vinylidene cyanide, vinyl chloride, vinylidene chloride, vinylidene fluoride, tetrafluoroethylene, vinyl furane, vinyl carbazole, vinyl acetylene and mixtures thereof.  Specified coupling agents are b -naphthol; 2-naphthol-7-sulphonic acid; 6-amino and 7-amino-a -naphthol; a mixture of 2, 3-oxynaphthoic acid, b -naphthol and 2-naphthol-7-sulphonic acid; 8-amino-a -naphthol; acetyl derivatives of 4-amino-a -naphthol; 2, 3-oxynaphthoic acid anilide, p-nitranilide, #s-toluidide, #s-anisidide, p-anisidide, m-nitranilide, a - and b -naphthalides, 4-chloro-#s-toluidide, m-chloro-#s-anisidide, #s-chloranilide and p-methoxy-#s-toluidide; and the 2, 5-dimethoxyanilides of 2-oxydibenzofurane-3-carboxylic acid and 2, 3-oxynaphthoic acid. The polymers may be dyed in granular form or in the form of shaped articles such as fibres, filaments and films by reacting with diazotized bases, of which many examples are given.  The products may also be used for casting and moulding, and in coating compositions and lacquers.  Artificial fibres and films may be prepared by spinning the above described polymers, e.g. from solutions in solvents such as N, N-dimethylacetamide, into precipitating baths, e.g. of water, the products being washed and dyed by immersion in solutions of diazotized bases and thereafter rinsed and dried.  The preparation and dyeing of films is also referred to, and examples describe the dyeing of filaments of (1) acrylonitrile-vinyl acetate copolymers, (5) methyl methacrylate polymers and (6) vinylidene chloride polymers, all modified with the anilide of 2, 3-oxynaphthoic acid.  U.S.A. Specification 2,431,956 is referred to.ALSO:Filaments, fibres and films prepared by spinning or extruding polymers obtained by polymerizing olefinically unsaturated monomers in the presence of naphthol coupling components, the polymers containing said coupling components chemically bound to the molecular structures of the polymers in amounts from 0,5 to 6,0% by weight of the polymers (see Group IV(a)), are dyed by immersing in solutions of diazotized bases.  Specified monomers are vinyl acetate, vinyl ethenyl carbinols, methyl vinyl ketone, methyl isopropenyl ketone, methyl vinyl ether, ethylene, propylene, styrene, chlorostyrene, p-methoxystyrene, a -methylstyrene, vinyl naphthalene, acrylic acid, methacrylic acid, acrylonitrile, methacrylamide, methyl acrylate, ethyl acrylate, isobutyl acrylate, methyla -chloracrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, diallylmaleate, fumaric acid esters, vinylidene cyanide, vinyl chloride, vinylidene chloride, vinylidene fluoride, tetrafluoroethylene, vinyl furane, vinyl carbazole, vinyl acetylene and mixtures thereof.  Many suitable coupling components are listed and the use of the anilide, b -naphthalide and #s-toluidide of 2, 3-oxynaphthoic acid is described.  Many suitable bases are also listed.  Examples describe the spinning of filaments, from solutions in N, N-dimethylacetamide into precipitating baths of water, of polymers of (I) acrylonitrilevinyl acetate, (V) methyl methacrylate and (VI) vinylidene chloride, all modified with the anilide of 2, 3 oxynaphthoic acid and the dyeing thereof with diazoiized (I) Fast Orange GC base and (V and VI) Fast Violet B, Fast Red KB and Fast Blue B bases.  U.S.A.  Specification 2,431,956 is referred to.