Furfural-Based Vinyl Ester Resins: Syntheses, Properties and Comparison to Bisphenol A-Glycidyl Methacrylate-Based Vinyl Ester Resin

The environmental impact of using fossil-based resources in polymer production has raised serious concerns in recent decades. As a response, the development of renewable alternatives has garnered significant interest. In this study, we report the syntheses of two renewable sulfur-bridged dimethacrylates via three-step routes starting from commercial 5-bromofurfural. The dialdehyde and aldehyde intermediates were obtained using sodium sulfide and 2-mercaptoethanol, respectively, followed by reduction to diols and subsequent methacrylation using methacrylic anhydride (MAA). The properties of the resulting biobased dimethacrylates were compared to those of a commercially available petroleum-based vinyl ester resin and its neat monomer, bisphenol A-glycidyl methacrylate (BisGMA). The difuran-based monomer was a waxy solid at room temperature but exhibited low viscosity in its liquid state at elevated temperature, while the unsymmetrical monomer, containing a single furan ring, showed low viscosity already at room temperature – highlighting their favorable processing characteristics. Upon curing, both bioresins formed highly cross-linked networks with outstanding glass transition temperatures (183 and 162 °C), while thermal decomposition took place at 251 and 285 °C. Tensile strengths were approximately 46 and 16 MPa. Furthermore, both materials demonstrated chemical and water resistance comparable to that of their fossil-based counterpart. The results support the potential of these dimethacrylates as renewable alternatives to widely utilized fossil-based vinyl ester resins in various applications.