Abietic Acid Derivatives Combining Epoxy and Anhydride Functionalities: Self- and Co-Polymerization toward Fully...

We report the original synthesis of two abietic acid derivatives, epoxidized maleopimarate oleylamide (EMPOA) and epoxidized maleopimarate undecenamide (EMPUA), which uniquely combine epoxy and anhydride functions within a single molecular structure. Their ability to undergo self-polymerization was first investigated, and fully cross-linked thermosets were subsequently obtained by copolymerizing EMPOA and EMPUA with a series of commercial biobased epoxides derived from vanillin, glycerol, and vegetable oils. A key advantage of EMPOA lies in its excellent miscibility with epoxidized vegetable oils, providing low-viscosity mixtures that can be readily blended with other epoxy resins without requiring large amounts of solvent. Epoxidized soybean oil (ESBO) proved to be an efficient reactive diluent, reducing solvent use to trace levels. Cross-linked materials with glassy-state moduli in the gigapascal range, comparable to fossil-based thermosets, were obtained. These results establish EMPOA and EMPUA as promising dual-reactive monomers for the design of high-performance and fully biobased thermosetting materials.