Renewable and recyclable covalent adaptable networks based on bio-derived lipoic acid

Maher Alraddadi, Viviane Chiaradia, Connor Stubbs, Josh Worch, Andrew Dove

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Abstract

The modern materials economy is inefficient since most products are principally derived from non-renewable feedstocks and largely single-use in nature. Conventional thermoset materials are often inherently unreprocessable due to their irreversible covalent crosslinks and hence are challenging to recycle and/or reprocess. Covalent adaptable networks (CAN)s, which incorporate reversible or dynamic covalent bonding, have emerged as an efficient means to afford reprocessable crosslinked materials and increasing the feedstock sustainability of CANs is a developing aim. In this study, the biomass-derived lipoic acid, which possesses a dynamic cyclic disulfide moiety, was transformed into a series of bifunctional monomers via a one-step esterification or amidation reaction and reacted with a commercially available multi-valent thiol in the presence of an organobase catalyst to afford dynamically crosslinked networks. Large differences in material properties, such as storage modulus and glass transition temperature, were observed when the ratio of the lipoic acid-based monomer to thiol (from 1 : 1 to 16 : 1) and the composition of the monomer were changed to modify the network architecture. The thermomechanical properties of an optimised formulation were investigated more thoroughly to reveal a moderately strong rubber (ultimate tensile strength = 1.8 ± 0.4 MPa) possessing a large rubbery plateau (from 0 to 150 °C) which provides an adaptable material with a wide operational temperature range. Finally, the chemical recycling, or depolymerisation, of the optimised network was also demonstrated by simply solvating the material in the presence of an organobase catalyst.

Original languageEnglish
Pages (from-to)5796-5802
Number of pages7
JournalPolymer Chemistry
Volume12
Issue number40
Early online date17 Sept 2021
DOIs
Publication statusPublished - 28 Oct 2021

Bibliographical note

Funding Information:
A. P. D., J. C. W. and C. J. S. acknowledge funding from the European Research Council (ERC) under the European Union’s Horizon 2020 research and innovation programme under grant agreement no. 681559. V. C. acknowledges funding from Unilever. M. A. thanks The Royal Commission for Jubail and Yanbu (RCJY) for support funding.

Publisher Copyright:
© 2021 The Royal Society of Chemistry.

Keywords

  • Organic Chemistry
  • Polymers and Plastics
  • Biochemistry
  • Bioengineering

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