Polymeric Antioxidant via ROMP of Bioderived Tricyclic Oxanorbornene Based on Vanillin and Furfurylamine

Abstract

Herein, a bioderived antioxidant oxanorbornene lactam monomer bearing a vanillyl moiety has been successfully synthesized. The monomer was synthesized via reductive amination of two biobased molecules, vanillin and furfurylamine, followed by tandem Diels–Alder and lactamization reactions with maleic anhydride. For comparison, an inactive monomer was prepared using benzaldehyde instead of vanillin. Rapid controlled polymerization of the tricyclic strained monomers has been conducted using ring opening metathesis polymerization. The resultant polymers were fully characterized, and their antioxidant potentials had been assessed. The monomer with the vanillyl moiety and its corresponding polymer showed exceptional antioxidant activities compared to the reference analogue with a benzyl pendant group. Indeed, the developed antioxidant polymer shows promising potential in the sustainable polymer industry for a smaller ecological footprint.