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Chemically Recyclable, High Molar Mass Polyoxazolidinones via Ring Opening Metathesis Polymerization
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Researchers developed chemically recyclable polyoxazolidinones (POxa) -- polymers with five-membered urethanes in their backbone -- via ring opening metathesis polymerization, achieving high molar mass materials with tunable properties. The approach demonstrates a viable route to next-generation recyclable polymers as alternatives to conventional non-recyclable urethane-based materials.
The development of robust methods for the synthesis of chemically recyclable polymers with tunable properties is necessary for the design of next-generation materials. Polyoxazolidinones (POxa) – polymers with five-membered urethanes in their backbones – are an attractive target because they are strongly polar and have high thermal stability, but existing step-growth syntheses limit molar masses and chemical recyclability to monomer is rare. Herein, we report the synthesis of high molar mass POxa via ring opening metathesis polymerization of oxazolidinone-fused cyclooctenes. These novel polymers show <5% mass loss up to 382–411 °C and have tunable glass transition temperatures (14–56 °C) controlled by side chain structure. We demonstrate facile chemical recycling to monomer and re-polymerization despite moderately high monomer ring strain energies, which we hypothesize is facilitated by the conformational restriction introduced by the fused oxazoli-dinone ring. This method represents the first chain growth synthesis of POxa and provides a versatile platform for the study and application of this emerging subclass of polyurethanes.
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