Patent GB-851773-A (GB)
Title: N-vinyl-x-alkyl-2-oxazolidinones and their polymers
IPC: C07D263/22
Filed: 1958-09-05
Abstract: The invention comprises polymers having as a constituent of their polymeric structures the recurring group <FORM:0851773/IV(a)/1> wherein the Xs are independently selected from hydrogen and C1-4 alkyl groups, at least one X being such an alkyl group.  The polymers may be prepared by the polymerisation of an N-vinyl-4- and/or 5-alkyl-2-oxazolidinone <FORM:0851773/IV(a)/2> the Xs being as before defined, alone, with one another, or in conjunction with other ethylenically unsaturated compounds such as N-vinyl-2-oxazolidinone, styrene, vinyl toluene, acrylonitrile, vinyl chloride, vinylidene chloride, vinyl acetate, vinyl propionate, methyl acrylate or methacrylate and ethyl acrylate. Polymerization may be effected in bulk, solution, emulsion or dispersion suitably at 50-100 DEG C.; suitable catalysts are azo and peroxy catalysts and various forms of irradiation including that from radioactive materials and high energy electron beams. Polymers having K values of more than 100 may be formed.  They may be incorporated in synthetic textile fibres and other shaped articles especially for those produced from the acrylonitrile polymers as dyeing adjuvants.  In Examples (4) N-vinyl-5-methyl-2-oxazolidinone is polymerized in dioxane yielding a polymer powder which on being incorporated in polyacrylonitrile fibres aids their dyeing; (5) N-vinyl-5-ethyl-2-oxazolidinone is similarly polymerized and used in a hair setting composition comprising dimethyl phthalate, denatured ethanol and chloro fluoro methanes.  Specification 807,016 is referred to.ALSO:The invention comprises N-vinyl alkyl-ring substituted-2- oxazolidinones of the general formula:  <FORM:0851773/IV(b)/1> wherein each X represents a hydrogen atom or a C1-4 alkyl group, not more than 3 of the substituents being hydrogen.  They may be prepared by the transvinylation of an appropriate C-alkylsubstituted 2-oxazolidinone with a C1-10 alkyl (including cyclo alkyl) vinyl ether in the presence of up to 10% by weight of the reaction mixture of mercuric acetate and/or mercuric benzoate, zinc acetate or phenyl mercuric acetate, preferably in an inert solvent and an inert atmosphere and, if desired, under pressure ; reaction temperatures of about 110 DEG -170 DEG C. are suitable.  The compounds may be polymerised and the polymers used as dyeing assistants for synthetic textile fibres (see Group IV(a)) or in hair-setting formulations (see Group IV(c)).  The monomers may be brominated at the vinyl group by treatment with bromine in chloroform.  In examples, (1) 5-methyl-2-oxazolidone is reacted with nbutyl vinyl ether in dioxane, using mercuric acetate and benzoic acid as catalyst, in an autoclave at 165 DEG C. yielding 5-methyl-N-vinyl-2-oxazolidinone; (2) as in (1) using ethyl vinyl ether and phenyl mercuric acetate as catalyst; (3) 5-ethyl-2-oxazolidinone is reacted as in (1) yielding N-vinyl-5-ethyl-2-oxazolidinone.  N-vinyl-4-ethyl- and 4,5-diethyl- 2-oxazolidinones are referred to.  Specification 807,016 is referred to.ALSO:Hair setting compositions comprise polymers of N-vinyl -5- ethyl -2- oxazolidinone.  Example 5 describes an aerosol composition comprising a polymer as above of K- value 16,4, dimethyl phthalate, denatured ethanol and chloro fluoro methanes.