From the Design of Multifunctional Degradable Epoxy Thermosets to Their End of Life

Abstract

The development of multifunctional epoxy thermosets that meet the requirements of sustainable development by creating new macromolecular architectures, i.e., novel epoxy monomers, is a real challenge. Herein, a bis-imidazolium cycloaliphatic epoxidized room temperature ionic liquid (CEIL) was successfully synthesized at multigrams scale (1–200 g) and used as molecular brick platforms to design various networks combined to a computational approach. Thus, three epoxy networks were developed by cationic polymerization using CEIL and 3,4-epoxycyclohexylmethyl-3′,4′-epoxycyclohexane carboxylate (ECC) in the presence of a thermoacid initiator. The CEIL-based networks presented higher thermal stabilities (>450 °C) and good mechanical performances combined for promising shape memory behavior. Most importantly, the incorporation of this ionic molecular brick, i.e., CEIL monomer in the architecture of the networks (50% or 100%), addresses the concept “design to degrade” inducing full degradability for the first time under mild working conditions (up to 99.4% of p-CEIL dissolution in 4.5 h).