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Recyclable and malleable thermosets enabled by activating dormant dynamic linkages
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Recyclable and malleable thermosets enabled by activating dormant dynamic linkages
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Journal Article
Recyclable and malleable thermosets enabled by activating dormant dynamic linkages
2022
Overview
Chemical recycling of polymers is critical for improving the circular economy of plastics and environmental sustainability. Traditional thermoset polymers have generally been considered permanently crosslinked materials that are difficult or impossible to recycle. Herein, we demonstrate that by activating ‘dormant’ covalent bonds, traditional polycyanurate thermosets can be recycled into the original monomers, which can be circularly reused for their original purpose. Through retrosynthetic analysis, we redirected the synthetic route from forming conventional C–N bonds via irreversible cyanate trimerization to forming the C–O bonds through reversible nucleophilic aromatic substitution of alkoxy-substituted triazine derivatives by alcohol nucleophiles. The new reversible synthetic route enabled the synthesis of previously inaccessible alkyl-polycyanurate thermosets, which exhibit excellent film properties with high chemical resistance, closed-loop recyclability and reprocessing capability. These results show that ‘apparently dormant’ dynamic linkages can be activated and utilized to construct fully recyclable thermoset polymers with a broader monomer scope and increased sustainability.
Alkyl and aryl polycyanurate networks have now been prepared through polymerization of diols and substituted triazines via a dynamic S
N
Ar reaction. When treated with excess mono alcohol or phenol, the polycyanurate networks can be depolymerized into the starting monomers, which can be separated and reused, thus achieving closed-loop recycling.
