Chemically Recyclable and Upcyclable Epoxy Resins Derived from Vanillin

Epoxy resins constitute a very significant portion of all high-performance plastics due to their excellent thermal and mechanical properties that appear in a wide range of applications. Nevertheless, traditional epoxy networks show limitations regarding chemical recycling due to their covalently crosslinked structures. The current methods to recycle epoxy resins are not indeed through sustainable ways, but this issue could be solved by developing smart monomers with functional groups, which can be switched between polymerized and depolymerized states. Herein, we developed two bio-based liquid monomers based on vanillin structures containing aldehyde, acetal, and oxirane-ring functionalities. These monomers were polymerized in solvent-free conditions using commercially available diamines, resulting in double-dynamic imine-acetal-containing thermosets. These networks combine the excellent properties of the traditional epoxy systems and dynamic polymers. Most importantly, such thermosets were fully depolymerized into vanillin, which can be reused for the preparation of original epoxy monomers, and a mixture of well-defined polyols, which was upcycled into high-performance polyurethane.