The Activators Regenerated by Electron Transfer Atom Transfer Radical Polymerization (ARGET-ATRP) of vanillin methacrylate (VMA), a bio-based methacrylic monomer derived from vanillin, was systematically studied for the first time. The reaction conditions were optimized aiming at achieving good monomer conversions while preserving the antimicrobial aldehyde functionality. Bipyridine-based catalysts showed limited effectiveness, whereas polydentate aliphatic amines displayed higher activity. Kinetic studies showed linear profiles during the early stages of the polymerization before reaching a conversion plateau accountable to the depletion of the reducing agent, as confirmed by reactivation experiments. The resulting polymer (PVMA) exhibited a glass transition temperature comparable to that of poly(styrene), emerging as a potential bio-derived alternative to fossil-based thermoplastic materials. Furthermore, preliminary in vitro tests demonstrated that PVMA has potential antimicrobial activity against both Escherichia coli (Gram-negative) and Bacillus subtilis (Gram-positive).
Marelli et al. (Thu,) studied this question.