Resin-to-Resin Circularity in Chemical Recycling of Dicyclopentadiene-Based Cycloolefin Resins

Cycloolefin resins (CORs) comprising dicyclopentadiene (DCPD) cross-linkers are high performance thermosets for diverse single-use applications. If it were possible to carry out deconstruction of DCPD thermosets through exclusive reformation of the cyclopentene ring in DCPD, then linear polyDCPD chains could re-enter subsequent manufacturing cycles and enable resin-to-resin circularity. Here, we develop a chemical recycling process whereby linear polyDCPD recyclates are generated from end-of-life commercial and model CORs, including copolymers, using a second-generation Hoveyda-Grubbs ruthenium(II) alkylidene catalyst for deconstruction via ring-closing metathesis. The properties of first-generation DCPD thermosets were reproduced across subsequent generations of recycling and reuse, where up to 84% of linear DCPD was retrievable from end-of-life thermosets after deconstruction. We further quantify how comonomer incorporation, the curing process, and aging affect round-trip material efficiency and the quality of regenerated thermosets.