Patent GB-807016-A (GB)
Title: A new vinyl monomer and polymerization products thereof
IPC: C07D263/20
Filed: 1955-05-11
Abstract: The invention comprises polymers of N-vinyl-2-oxazolidone or copolymers thereof with one or more copolymerizable unsaturated compounds which are either (a) compounds containing a CH2=C< grouping, or (b) polymerizable unsaturated alkyd resins containing a plurality of polymerizably-reactive a  : b -enal groups <FORM:0807016/IV (a)/1> produced by reacting a polyhydric alcohol with an ethylenically unsaturated polycarboxylic compound wherein the ethylenically unsaturated grouping is alpha to a carbonyl group.  The comonomers (a) may be nitriles, amides, ethers, alcohols and ketones, unsaturated mono- and poly-hydric alcohol esters of saturated or unsaturated aliphatic, aromatic, mono-or poly-carboxylic acids, vinyl-substituted cycloaliphatic, aromatic or heterocyclic compounds, methylene malonic esters, vinyl halides, vinylidene compounds-many examples of all these classes being given-and ethylene, butadienes, diallyl carbonate, thiallyl cyanurate, various allyl-silicon compounds and allyl and methallyl phosphates.  Numerous reaction mixtures for making the alkyd resins (b) are listed, some including modifying ingredients, for example, ethylene glycol + maleic anhydride \sB succinic acid, tetrafluoro-succinic acid, stearic acid or a mixture of phthalic anhydride and linseed oil acids or of octyl alcohol and acetic acid as modifier; diethylene glycol + fumaric acid + either linseed oil acids and tetrahydroabietyl alcohol, or benzyl alcohol or linseed oil acid monoglycerides.  The mixtures of compounds (a) and/or (b) with the vinyl oxazolidone normally contain at least 10 per cent of the latter.  The polymerization and copolymerization may be effected with the aid of heat, light or a catalyst of which many examples are given, and emulsion, bead, bulk or solution methods may be used.  Temperatures ranging from 20 DEG C. to the normal boiling-point or higher are utilizable. The materials may be used in the production of castings, adhesives, for instance in the production of such optical devices as compound lenses and prisms, and in the treatment of paper or paper stock.  They may be used in moulding compositions, if desired with fillers such as a -cellulose pulp, asbestos fibres, cotton flock, glass fibres, wood flour, antimony oxide, titanium dioxide, sand, mica dust or diatomaceous earth, under moulding conditions of, for example, temperatures from 120-200 DEG  C. and pressures of 1000-10,000 p.s.i. Mixtures of the vinyl oxazolidone and resin (b) may be used in bonding sheets of fibrous material to produce laminated articles (see Group VIII).  Other uses of the products are mentioned in some of the following typical examples: (3) and (5) N-vinyl oxazolidone is homopolymerised by heating with the aid of benzoyl peroxide or by exposure to ultra-violet light; (12 to (16) N-vinyl oxazolidone is bulk polymerized with acrylonitrile, methyl methacrylate, vinyl acetate or vinylidene chloride, using azodiisobutyronitrile as catalyst; the vinylidene copolymer can be drawn into rods or tubes; (8) styrene is copolymerized with N-vinyl oxazolidone in aqueous emulsion yielding a latex suitable for coating glass, metal or wood; the latex may be coagulated by means of a metal salt or acid and the copolymer can then be moulded, if desired, with a dye, pigment, plasticiser or other modifying agent; (10) diallyl tetrafluoro succinate, triallyl cyanurate and N-vinyl oxazolidone are copolymerized to yield a product suitable for making flame-resistant laminated articles; (17) acrylamide or methacrylamide is polymerized with N-vinyl oxazolidone, yielding a water-soluble copolymer suitable as such or in the form of a formaldehyde reaction product in textile-sizing, adhesive, paper and soil conditioning and stabilizing compositions; (19) an ethylene glycol-fumaric acid-sebacic acid polyester, N-vinyl oxazolidone, wood flour, and benzoyl peroxide are admixed and moulded in a disc mould; (22) a similar polyester, N-vinyl oxazolidone, paraformaldehyde and benzoyl peroxide, together with triphenyl phosphate filler, are heated together at 100 DEG  C. to provide a solid porous resin.ALSO:The invention comprises N-vinyl-2-oxazolidone which may be prepared by the dehydrochlorination of N-(b -chloroethyl)-2-oxazolidone in the presence of an hydrogen halide acceptor.  In an example, equimolar amounts of diethanolamine and diethyl carbonate are heated together at 110-135 DEG  C., yielding N-(b -hydroxyethyl)-2-oxazolidone which is reacted with thionyl chloride in benzene and the resulting hydrohalide salt of N-(b -chloroethyl)-2-oxazolidone is treated with sodium bicarbonate to liberate the free b -chloroethyl oxazolidone; the latter is dehydrochlorinated to N-vinyl-2-oxazolidone by heating under reflux with potassium t.-butoxide in t.-butanol.  The vinyl oxazolidone may be polymerized alone or with copolymerizable compounds (see Group IV (a)) and may be used in forming laminated articles or coating compositions (see Group VIII).ALSO:Soil-stabilising and -conditioning compositions comprise water-soluable copolymers of N-vinyl-2-oxazolidore and acrylamide or methacrylamide, or the formaldehyde reaction products of the copolymers.  The preparation of the copolymers is described (see Group IV(a)].