The Introduction of Hydroxyl Functionality Into Polymers: The Synthesis, Polymerization, and Hydrolysis of Vinylbenzyl Acetate

Vinylbenzyl acetate was synthesized in yields greater than 80% via the reaction of vinylbenzyl chloride with potassium acetate. Radical copolymerizations of the monomer with styrene and methyl methacrylate were studied at 60 deg C. Reactivity ratios determined from FT-IR analysis of low conversion copolymerizations with styrene (M sub 1 ) were r sub 1 = 0.78 plus/minus 0.07 and r sub 2 = 1.33 plus/minus 0.13. Polymers and copolymers of vinylbenzyl acetate were found to completely hydrolyze in dioxane /water/base solution to yield hydroxymethyl functionality. Size exclusion chromatography studies indicated that the hydrolysis proceeded without crosslinking. This procedure is a useful method for the introduction of hydroxyl functionality on polymers and avoids crosslinking problems common in previously reported methods. 21 ref.--AA