Thermally reversible nanocellulose hydrogels synthesized via the furan/maleimide Diels-Alder click reaction in water

Int J Biol Macromol. 2019 Dec 1:141:493-498. doi: 10.1016/j.ijbiomac.2019.09.027. Epub 2019 Sep 5.

Abstract

The study deals with the synthesis of thermally reversible hydrogels from modified cellulose nanofibers via the Diels-Alder "click" reaction in an aqueous medium. "Never-dried" cellulose fibres derived from hardwood were submitted to shearing and surface TEMPO-oxidation before being modified with furfurylamine. The ensuing pendant furan moieties were reacted with a water-soluble bismaleimide via Diels-Alder coupling at 65 °C to produce a hydrogel, whose deconstruction was induced by the corresponding retro-Diels-Alder reaction carried out at 95 °C. Differential scanning calorimetry and rheological measurement were used to characterize the hydrogels. These aqueous cellulosic materials should provide original applications in such areas as strong paper-based artefacts and biocompatible gels.

Keywords: Diels-Alder; Nanofiber cellulose; Thermoreversible hydrogel.

MeSH terms

  • Cellulose / chemistry*
  • Cycloaddition Reaction*
  • Furans / chemistry*
  • Hydrogels* / chemical synthesis
  • Hydrogels* / chemistry
  • Maleimides / chemistry*
  • Water

Substances

  • Furans
  • Hydrogels
  • Maleimides
  • Water
  • maleimide
  • Cellulose
  • furan