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

• Published in: Progress in organic coatings 2022-09, Vol.170, p.106996, Article 106996
• Main Authors: Kalita, Deep J., Tarnavchyk, Ihor, Selvakumar, Sermadurai, Chisholm, Bret J., Sibi, Mukund, Webster, Dean C.
• Format: Article
• Language: English
• Subjects: Air-drying; Alkyd resins; Bio-based; Cationic polymerization; Coatings; Copolymerization; Copolymers; Crosslinking; Drying; Glass transition temperature; Mechanical properties; Modulus of elasticity; Monomers; Polymerization; Polymers; Polyvinyl ethers; Renewable; Temperature; Thermomechanical properties; Vinyl ether
• ISSN: 0300-9440; 1873-331X
• DOI: 10.1016/j.porgcoat.2022.106996

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. [Display omitted] •Novel vinyl ether monomer was synthesized from biobased compound eugenol.•Polymers from eugenol-based monomer were produced via carbocationic polymerization.•The produced polymers can undergo autoxidation through allylic moieties of eugenol.•Coatings cured via autoxidation show properties better than those from alkyd resins.•Crosslinked eugenol-based coatings show excellent base resistance.