Intrinsically re-curable photopolymers containing dynamic thiol-Michael bonds

Research output: Contribution to journalArticlepeer-review

Abstract

The development of photopolymers that can be depolymerized and subsequently re-cured using the same light stimulus presents a significant technical challenge. A bio-sourced terpenoid structure, l-carvone, inspired the creation of a re-curable photopolymer in which the orthogonal reactivity of an irreversible thioether and a dynamic thiol-Michael bond enables both photopolymerization and thermally driven depolymerization of mechanically robust polymer networks. The di-alkene containing l-carvone was partially reacted with a multi-arm thiol to generate a non-crosslinked telechelic photopolymer. Upon further UV exposure, the photopolymer crosslinked into a mechanically robust network featuring reversible Michael bonds at junction points that could be activated to revert, or depolymerize, the network into a viscous telechelic photopolymer. The regenerated photopolymer displayed intrinsic re-curability over two recycles while maintaining the desirable thermomechanical properties of a conventional network: insolubility, resistance to stress relaxation, and structural integrity up to 170 °C. Our findings present an on-demand, re-curable photopolymer platform based on a sustainable feedstock.
Original languageEnglish
Pages (from-to)11729–11735
Number of pages7
JournalJournal of the American Chemical Society
Volume144
Issue number26
Early online date24 Jun 2022
DOIs
Publication statusPublished - 6 Jul 2022

Bibliographical note

Funding Information:
A.P.D., J.C.W., and C.J.S. acknowledge the funding from the European Research Council (ERC) under the European Union’s Horizon 2020 research and innovation program under the grant agreement no. 681559. A.K. acknowledges the funding from the University of Birmingham. V.C. acknowledges the funding from Unilever.

Keywords

  • photopolymer
  • l-carvone
  • Michael bonds
  • telechelic

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