Diels-Alder-Chitosan based dissociative covalent adaptable networks

Camille Chapelle; Baptiste Quienne; Céline Bonneaud; Ghislain David; Sylvain Caillol

doi:10.1016/j.carbpol.2020.117222

Diels-Alder-Chitosan based dissociative covalent adaptable networks

Carbohydr Polym. 2021 Feb 1:253:117222. doi: 10.1016/j.carbpol.2020.117222. Epub 2020 Oct 14.

Authors

Camille Chapelle¹, Baptiste Quienne¹, Céline Bonneaud¹, Ghislain David², Sylvain Caillol¹

Affiliations

¹ ICGM, Univ Montpellier, CNRS, ENSCM, Montpellier, France.
² ICGM, Univ Montpellier, CNRS, ENSCM, Montpellier, France. Electronic address: ghislain.david@enscm.fr.

PMID: 33278984
DOI: 10.1016/j.carbpol.2020.117222

Abstract

For the first time, Diels-Alder and retro Diels-Alder reactions were evidenced by ¹H NMR spectroscopy and DSC on chitosan based systems. At first, preliminary studies led to structural identification and better understanding of the Diels-Alder reaction. Then, chitosan of 30,000 g/mol and 150,000 g/mol were modified by furfuryl glycidyl ether with 20% substitution degree. The resulting products were cross-linked with bis and trismaleimide crosslinkers to produce films possessing interesting mechanical properties. Unprecedented for chitosan-based films, DMA measurement highlighted retro Diels-Alder between 110 and 130 °C. Films showed interesting hydrophobicity and fat absorption. They also exhibited resistance in acidic media whereas crude chitosan films were dissolved.

Keywords: Chitosan-based films; Diels-Alder crosslinking; thermoresponsive materials; trismaleimide.