Poly (vinyl ethers) based on the biomass-derived compound, eugenol, and their one-component, ambient-cured surface coatings

Abstract

A novel monomer, 2-eugenoloxy ethyl vinyl ether (EEVE), was produced from a renewable bio-based compound, eugenol. EEVE was homopolymerized and copolymerized with cyclohexyl vinyl ether (CHVE) via carbocationic polymerization to produce linear polymers. These eugenol-based polymers were evaluated for their ability to produce alkyd-type surface coatings via autoxidative crosslinking. The EEVE-based polymers can provide several advantages over conventional air-drying alkyd resins such as energy-efficient polymerization, precise control over composition and molar mass, and elimination of issues associated with gelation during polymerization. The EEVE-based coatings showed significantly higher chemical resistance, hardness, glass transition temperature, and Young's modulus compared to a commercial alkyd coating. The base resistance of EEVE-based coatings was significantly improved compared to conventional air-drying alkyd resins. As expected, incorporation of the CHVE to the poly(vinyl ether) polymer backbone significantly increased the glass transition temperature and mechanical properties of the crosslinked networks. The optimum physical and thermomechanical properties for the EEVE/CHVE copolymers were obtained at 25 wt% loading of CHVE monomer. Overall, the results of the study suggest a high potential for these eugenol-derived biobased monomers and polymers for applications in air-drying coatings.