Patent GB-935787-A (GB)
Title: Triazine derivatives and polymers thereof
IPC: C08F283/01
Filed: 1961-08-14
Abstract: Compounds of the general formula <FORM:0935787/IV(a)/1> in which R is vinyl or isopropenyl and the R1s, which may be the same or different, are vinyl, isopropenyl, C1-C4 alkyl or halogen substituted C1-C4 alkyl, are used in the formation of homopolymers and copolymers.  In the formation of copolymers they may be polymerized with, for example, methyl acrylate, ethyl acrylate, butyl acrylate, iso-butyl acrylate, methyl methacrylate, styrene, vinyltoluene, acrylic acid, methacrylic acid, vinyl ethers, vinyl ketones, vinyl pyridines, acrylonitrile, vinylidene chloride and polymerizable unsaturated alkyd resins, e.g. ethylene glycol maleate, diethylene glycol maleate phthalate.  The polymerization may be carried out by heating the monomer or monomers in the presence of a catalyst alone or in a solution or aqueous emulsion.  Chainmodifying agents or chain terminators such as the mercaptans may be added to the mixture.  In the examples: (a) 2,4-dimethyl-6-vinyl-s-triazine is polymerized by heating in the presence of azo bis-isobutyronitrile and (b) 2,4-dimethyl-6-vinyl-s-triazine is polymerized with acrylonitrile. Specifications 905,545 and 917,845 are referred to.ALSO:The invention comprises s-triazine compounds of the structural formula <FORM:0935787/IV(a)/1> in which R is a lower alkenyl radical and R1 is a lower alkenyl radical, a lower alkyl radical or a halogen-substituted lower alkyl radical.  The "lower" alkenyl radical is a vinyl or isopropenyl radical and the lower alkyl radicals are those containing 1-4 carbon atoms.  The two R1 radicals may be the same or different.  The new compounds are prepared by eliminating the molecule R2OH, in which R2 is a hydrogen atom or an acetyl group, by dehydrating or pyrolysis respectively from the corresponding 1-(or 2-) hydroxyalkyl or 1-(or 2-)acetoxyalkyl-s-triazine.  A list of new compounds given includes those in which R is vinyl and the R1 groups, which may be the same or different, are C1-C4 alkyl groups, vinyl or isopropenyl groups; trichloro-, tribromo- or trifluoromethyl groups; pentachloro-, pentabromo- or pentafluoro-methyl groups; or heptachloro-, heptabromo- or heptafluoro-propyl groups.  In the examples: (a) 2-(1-chloroethyl-4,6-dimethyl-s-triazine, obtained by the reaction of 2-chloropropionamidine hydrochloride with ethyl acetimidate, is treated with acetyl chloride and sodium acetate to give 2-(1-acetoxyethyl)-4,6-dimethyl-s-triazine which is pryolised to give 2,4-dimethyl-6-vinyl-s-triazine; (b) 2-(1-bromoethyl)-4,6-diethyl-s-triazine is acetylated as in (a) and is then pyrolysed to give 2,4-diethyl-6-vinyl-s-triazine; (c) 2-(1-chloroethyl)- 4,6-bis-(trifluoromethyl)- s-triazine, prepared by reacting 2-chloropropionamidine hydrochloride with trifluoroacetamidine, is acetylated to give 2-(1-acetoxyethyl)-4,6-bis-(trifluoromethyl)-s-triazine which is pyrolised to give 2,4-bis(trifluoromethyl)-6-vinyl-s-triazine; (d) p 2,4-bis-(1-chloroethyl)-6-methyl-s-triazine obtained as a by-product in the reaction of ethylacetamidate with 2-chloropropionamidine hydrochloride, is acetylated and the 2,4-bis(1-acetoxyethyl)-6-methyl-s-triazine is pyrolysed to give 2-methyl-4,6-divinyl-s-triazine; (e) 2,4,6-tris-(1-chloroethyl)-s-triazine is acetylated and the tri-acetoxyethyl compound obtained is pyrolysed to give 2,4,6-trivinyl-s-triazine; (f) 2-(2-hydroxyethyl)-4,6-dimethyl-s-triazine, prepared by condensing 3-hydroxypropionamidine hydrochloride with ethyl acetimidate is heated with P2O5 to give 2,4-dimethyl-6-vinyl-s-triazine; (g) 2-(2-hydroxyethyl)-4,6-dimethyl-s-triazine is reacted with vinyl chloride to give 2-methyl-4,6-divinyl-s-triazine; (h) 2-(2-hydroxyethyl)-4,6-dimethyl-s-triazine is heated with acetic anhydride to give 2,4-dimethyl-6-vinyl-s-triazine with some 2-(2-acetoxyethyl)-4,6-dimethyl-s-triazine and (j) 2-(2-acetoxyethyl)-4,6-dimethyl-s-triazine is heated to give 2-vinyl-4,6-dimethyl-s-triazine.  Specifications 905,545 and 917,845 are referred to.