Patent GB-755468-A (GB)
Title: Improvements in or relating to the production of polymerizable oxirane triazine
IPC: C08G73/06
Filed: 1954-06-14
Abstract: Polymerizable oxirane triazines have the general formula <FORM:0755468/IV(a)/1> wherein m is an integer from 1 to 3, n is an integer from 0 to 2, X is a halogen, Y is (a) hydrogen or an alkyl, alkenyl, aryl, alkaryl or aralkyl radical; (b) an amine radical having the formula -NRR1 where R and R1 are hydrogen, alkyl, alkenyl, aryl, alloaryl or aralkyl radicals; or (c) a radical of formula -OR11 where R11 is an alkyl, alkenyl, aryl, alkaryl or aralkyl radical; and G is a substituent of formula <FORM:0755468/IV(a)/2> where U is an alkylene radical and Z is hydrogen or an aliphatic radical, the total number of carbon atoms in substituent G being no more than 10.  The compounds may be cured by heating at 100 DEG  C. to 300 DEG  C., and may be used to prepare laminates, moulded objects, protective films, and may be used to impregnate fabrics, and as binding agents.  They may be used in conjunction with urea-formaldehyde resins, melamine-formaldehyde resins, phenolformaldehyde resins, polystyrene, polyamides, polyester amides, copolymers of polyesters and vinyl monomers, vinyl chloride and acrylonitrile, acrylonitrile and vinyl acetate, or with alkyd resins, epoxy resins and silicone resins. Examples (12 and 13) describe the preparation of a paper laminate and of films using dioxane solutions of triglycidyl cyanurate.  A list of compounds of the invention is given.ALSO:The invention comprises polymerizable oxirane triazines of formula <FORM:0755468/IV(a)/1> where m is an integer from 1 to 3 and n is an integer from 0 to 2; X is a halogen; Y is (a) hydrogen or an alkyl, alkenyl or aralkyl radical; or (b) an amine radical of formula -NRR1 where R and R1 are hydrogen or alkyl, alkenyl, aryl, alkaryl or aralkyl radicals; or (c) a radical of formula -OR11 where R11 is an alkyl, alkenyl, aryl, alkaryl or aralkyl radical; and G is a substituent having the formula <FORM:0755468/IV(a)/2> or <FORM:0755468/IV(a)/3> wherein U is an alkylene radical and Z is hydrogen or an aliphatic radical, the total number of carbon atoms in substituent G being no more than 10.  The oxirane triazines are prepared by reacting a monohalohydrin of a saturated aliphatic trihydric alcohol in the presence of a hydrogen halide acceptor with a halotriazine of formula <FORM:0755468/IV(a)/4> wherein n is an integer from 1 to 3, and X and Y are as above. The reaction is carried out at a temperature between 0 DEG  C. and 75 DEG C. in an inert solvent, such as dioxan, using an inorganic basic material, such as sodium hydroxide, as hydrogen halide acceptor. Lists are given of oxirane triazines according to the invention, and of suitable reactants.  In examples (1 to 3) triglycidyl cyanurate is obtained from cyanuric chloride and glycerol-a -monochlorohydrin; (4) 2 - glycidyl - 4,6 - dimethoxy - 1,3,5 - triazine is obtained from glycerol-a -monochlorohydrin and 2 - chloro - 4,6 - dimethoxy - 1,3,5 - triazine; (5) 2 - glycidyl - 4,6 - diphenoxy - s - triazine is obtained from glycerol-a -monochlorohydrin and 2 - chloro - 4,6 - diphenoxy - s - triazine; (2) 2-amino - 4 - glycidyl - 6 - s - triazine is obtained from glycerol - a  - monochlorohydrin and 2-amino - 4 - chloro - 6 - dibutylamino - s - triazine; (7) 2 - amino - 4 - glycidyl - 6 - phenylamino - s - triazine is obtained from glycerol-a  - monochlorohydrin and 2 - amino - 4 - chloro-6 phenylamino - s - triazine; (8) 2 - glycidyl-4,6 - di(phenoxy) - 1,3,5 - triazine is obtained from glycerol - a  - monochlorohydrin and 2-chloro - 4,6 - di(phenylamino) - 1,3,5 - triazine; (9) 2,4 - diglycidyl - 6 - p - tertiary butylphenoxy - s - triazine is obtained from glycerol - a -monochlorohydrin and 2,4 - dichloro - 6 - p-tertiarybutylphenoxy - s - triazine; (10) 2,4-glycidyl - 6 - phenoxy - s - triazine is obtained from glycerol-a -monochlorohydrin and 2,4-dichloro - 6 - phenoxy - s - triazine; and (11) a product is obtained from isomeric monochlorohydrins of 1,2,4-butanetriol and 2,4-dichloro-6-phenoxy-s-triazine