Patent GB-1083487-A (GB)
Title: Hydroxy-phenyl-1,3,5-triazines and their use in a process for the manufacture of polymers stabilized against the effects of ultraviolet rays
IPC: C08F12/08
Filed: 1965-11-24
Abstract: Polymers which absorb U.V. light are prepared by polymerizing with or without comonomers at least one compound of formula <FORM:1083487/C3/1> where U1 and U2 each represents a hydrogen atom, a chlorine atom or a methyl group, V1 and V2 each represents a hydrogen atom or a methyl group, and D stands for an alkenyl (up to 4 C) group.  Comonomers listed are vinyl esters of organic acids, vinyl alkyl ketones, vinyl halides, vinyl aryl compounds, esters, nitriles and amides of unsaturated acids, olefines, dienes, polymerizable heterocycles, and unsaturated ethers.  Binary, tertiary, or more complicated copolymers may be prepared by conventional methods.  A preferred copolymer is prepared from (a) monomers of the above formula, (b) esters of polymerizable acids not capable of absorbing ultraviolet rays, e.g. acrylic, crotonic, methacrylic or fumaric acid esters, and (c) a small proportion of free polymerizable acids, by bulk, solution or emulsion polymerization.  Graft polymers, e.g. with polyalkylenes, may also be prepared, preferably in an inert organic solvent, and this method may be used to incorporate the hydroxyphenyltriazines on the surface of polymers.  The compounds of the formula above may be used as stabilizers directly by fixing on polymers or copolymers to be protected, as a substrate containing the material to be protected or as a filter layer thereon.  Textiles (including those of vegetable origin), coating agents and lacquers (including those of cellulose and cellulose esters), resins (including alkyd resins), rubber-like materials and foils of regenerated cellulose are also stabilized. Examples describe the polymerization or copolymerization of acrylic esters corresponding to the formula above by heating in an organic solvent in the presence of azodiisobutyronitrile and/or benzoyl peroxide; comonomers used are styrene and n-butylacrylate, stearyl methacrylate, styrene, n-butylmethacrylate and methacrylic acid, prepolymerized styrene, methyl methacrylate, styrene, n-butylmethacrylate. Examples also describe graft polymerization with polyethylene; and emulsion polymerization with acrylonitrile, n-butyl acrylate and acrylic acid. Foils of polyethylene and polypropylene containing some of these polymers and copolymers, and a lacquer based on nitrocellulose containing dibutyl phthalate, arachis alkyd resin, a ketone-formaldehyde condensation resin, and conventional solvents with 1% of the polymer, are also exemplified.ALSO:The invention comprises triazine compounds of formula <FORM:1083487/C2/1> where U1 and U2 each represent a hydrogen atom, a chlorine atom or a methyl group, V1 and V2 each represent a hydrogen atom or a methyl group and D stands for an alkenyl (up to 4 C) group, and they may be polymerized or copolymerized.  The polymers are protected against the action of ultra-violet rays. The compounds are prepared by reacting a 21,41-dihydroxyphenyltriazine with an acid halide or acid anhydride in the presence of a tert.-amine in an inert organic solvent. Examples describe the reaction of 2,4-di-(21,41-dimethylphenyl) - 6 - (211,411 - dihydroxyphenyl)-1,3,5-triazine with 1,3-dimethylbenzene or resorcinol and pyridine or triethylamine with acrylylchloride or acrylylanhydride; 2-(41-chlorophenyl) - 4 - (211,411 - dimethylphenyl)-6 - (2111,4111 - dihydroxyphenyl) - 1,3,5 - triazine with triethylamine and acrylyl chloride; 2,4-diphenyl - 6 - (21,41 - dihydroxyphenyl) - 1,3,5-triazine with triethylamine and acrylylchloride; 2,4 - di - (41 - chlorophenyl) - 6 - (211,411 - di-hydroxyphenyl) - 1,3,5 - triazine with triethylamine and acrylylchloride; 2,4-di-(21,41-di-methylphenyl) - 6 - (211,411 - dihydroxyphenyl)-1,3,5-triazine with methacrylylchloride.  The polymers may also be incorporated in materials to be protected, either before or during manufacture of substrate material or incorporated in a filter layer.ALSO:<FORM:1083487/D1-D2/1> Protective agents against heat, air and ultraviolet light, for textile materials and paper comprise compounds of general formula:-where U1 and U2 each represent a hydrogen atom, a chlorine atom or a methyl group, V1 and V2 a hydrogen atom or a methyl group and D stands for an alkenyl group (up to 4C), their polymers or copolymers (see Divisions C2 and C3).  The stabilisers may be incorporated in the substrate during manufacture or by a subsequent fixing operation, or may be a solid or semi-solid 'filter layer' to protect the underlying substrate.ALSO:Protective agents for cosmetic preparations, e.g. perfumes, dyed or undyed soaps and bath salts, skin and face creams, powders, repellants, sunburn oils and creams against heat, air and ultraviolet rays comprise triazine compounds of formula: <FORM:1083487/A5-A6/1> where u1 and u2 each represents a hydrogen atom, a chlorine atom or a methyl group, V1 and V2 each represents a hydrogen atom or a methyl group and D stands for a alkenyl group (up to 4C), which may be polymerised or copolymerised (see Divisions C2 and C3).