Patent GB-889777-A (GB)
Title: Halogenated resbenzophenones and their etherified derivatives and compositions resistant to ultraviolet light
IPC: C08K5/136
Filed: 1959-05-04
Abstract: Materials normally subject to deterioration by ultra-violet light are stabilized by incorporating therein a compound having the formula <FORM:0889777/IV (a)/1> wherein R represents hydrogen or alkyl, X represents bromine or chlorine but is chlorine where R is hydrogen and Y represents hydrogen, bromine or chlorine (see Group IV(b)). Materials which may be stabilized include polyvinyl chloride and acetate and mixtures thereof, vinyl and vinylidene polymers and copolymers generally, polyester compositions prepared by reacting a ,b -unsaturated polycarboxylic acids with an aliphatic hydroxy compound especially a dihydric alcohol and admixing the polyester with a polymerizable ethylenically unsaturated compound, e.g. styrene or diallyl phthalate, acrylates, methacrylates, melamineformaldehyde resins, phenolics, nylon, and epoxy resins. Specific stabilizing agents described include 5-chloro-2,4-dihydroxy-, 5-bromo2-hydroxy-4-methoxy-, 3,5-dibromo-2-hydroxy4-methoxy-, 5-bromo-2-hydroxy-4-dodecoxyand 5-chloro-2-hydroxy-4-methoxy-benzo-phenones.  The preparation is described of films containing the stabilizers of the inventions by polymerization of polyester-styrene compositions in the presence of methyl ethyl ketone peroxide and from compositions comprising polyvinyl chloride, dioctylphthalate and cyclohexanone.  The polyesters employed in the above compositions are obtained by heating together diethylene glycol, maleic anhydride, phthalic anhydride and tetrabromophthalic anhydride or similar mixtures containing tetrachlorophthalic acid, 1,4,5,6,7,7-hexachloroendo - cis - bicyclo-[2,2,1]5-heptene-2,3-dicarboxylic acid in place of the phthalic anhydride or both the phthalic and tetra bromophthalic anhydrides.ALSO:The invention comprises a homonuclear halogenated resobenzophenone having the genera1 formula <FORM:0889777/IV (b)/1> wherein R represents hydrogen or alkyl, X represents bromine or chlorine but is chlorine when R is hydrogen, and Y represents hydrogen, bromine or chlorine.  A list of alkyl radicals which may be present is given extending from methyl to octadecyl and including various isomers.  The 5-chloro- and 3,5-dichloro-dihydroxy benzophenones are prepared by chlorinating a solution of resbenzophenone in an inert solvent, e.g. dioxane, a dialkyl ether, chlorobenzene, benzene, glacial acetic acid, chloracetic acid or mixtures thereof.  The 4-alkoxy-2-hydroxybenzophenones may be similarly halogenated or corresponding halogenated 2,4-dihydroxy-benzophenones mono-alkylated to obtain halogenated 4-alkoxy-2-hydroxy-benzophenones.  Dimethyl sulphate and dodecyl bromide are specified as alkylating agents.  In examples are described the preparations of 5-chloro- and 3,5-dichlororesbenzophenones and 5 - bromo - 2 - hydroxy - 4 - methoxy-, 3, 5 - dibromo - 2 - hydroxy - 4 - methoxy - 5 - chloro - 2 - hydroxy - 4 - methoxy-and 5 - bromo - 4 - dodecoxy - 2 - hydroxy - benzophenones.  The substituted benzophenones of the invention are incorporated as stabilisers in materials normally subject to deterioration on exposure to ultra-violet light, e.g. resinous condensation and polymerisation products (see Group IV (a)) and cellulose organic esters and regenerated cellulose.