Synthesis and Characterization of Methacrylated Eugenol as a Sustainable Reactive Diluent for a Maleinated Acrylated Epoxidized Soybean Oil Resin

This work presents a solvent-free, facile synthesis of a renewable, aromatic monomer, methacrylated eugenol (ME), from eugenol and methacrylic anhydride by the Steglich esterification reaction. The resulting ME was subsequently used as a reactive diluent to copolymerize with a commercial maleinated acrylated epoxidized soybean oil (MAESO) resin to form renewable MAESO-ME thermosets. The volatility of ME was examined, along with an analysis of viscosity and curing behavior of the MAESO-ME mixtures. The curing kinetics, thermo-mechanical properties, and thermal stabilities of the fully cured MAESO-ME thermosets with different ME proportions (0, 20, 40, 60, 80, and 100%) were systematically investigated. The results indicated that ME monomer exhibited extremely low volatility (less than 3% mass loss after being held isothermally at 30 °C for 10 h), high bio-based carbon content (BBC, 71.4%), and low viscosity (17.6 cP at 25 °C). When used with MAESO resin, viscosity of the system was considerably decreased. ...