(Co)Polymerization of vinyl levulinate by cobalt-mediated radical polymerization and functionalization by ketoxime click chemistry

Abstract

Vinyl levulinate is synthesized from levulinic acid by palladium-catalyzed vinyl exchange and is characterized by NMR and ESI-HRMS techniques. Homopolymerization of vinyl levulinate and random copolymerization with vinyl acetate by cobalt-mediated radical polymerization affords well-defined ketone functionalized poly(vinyl ester)s. The impact of temperature, solvent and theoretical degree of polymerization on monomer conversion and control of the polymerization is studied by ¹H NMR and size exclusion chromatography techniques. The ketoxime conjugation of O-benzylhydroxylamine with the pendant ketone functionality of poly(vinyl levulinate-co-vinyl acetate) is demonstrated.