Ultraviolet stabilizing monomers and polymers. I. Synthesis and polymerization of phenyl 5‐methacryloxymethylsalicylate

With a view to permanently incorporating ultraviolet stabilizing moieties into polymer systems, monomers containing the phenyl salicylate structure have been prepared and polymerized. Phenyl 5‐acryloxymethylsalicylate and phenyl 5‐methacryloxymethyl‐salicylate were prepared by the chloromethylation of phenyl salicylate and subsequent reaction with sodium acrylate or methacrylate. Homopolymers and copolymers of the methacryloxymethyl monomer were prepared and studied. The ultraviolet spectra of the chloromethyl derivative, the monomers, and the homopolymers were essentially similar to that of the starting material, phenyl salicylate. Copolymers of the ultraviolet‐absorbing monomers (2%) with vinyl acetate, vinylidene chloride, and vinyl chloride were prepared. The ultraviolet stability of these copolymers was then compared to that of an unstabilized control series and a series containing phenyl salicylate. While there were some differences in the behavior of the copolymerized absorber it was at least as effective as phenyl salicylate in stabilizing the polymers.