Sustainable design of vanillin-based vitrimers using vinylogous urethane chemistry. Issue 18 (20th April 2022)

• Record Type: Journal Article
• Authors: Engelen, Stéphanie; Wróblewska, Aleksandra Alicja; De Bruycker, Kevin; Aksakal, Resat; Ladmiral, Vincent; Caillol, Sylvain; Du Prez, Filip E.
• Is Part Of: Polymer chemistry. Volume 13:Issue 18(2022)
• Page Start: 2665
• Page End: 2673
• Publication Date: 2022-04-20
• Subjects: Polymers -- Periodicals; Macromolecules -- Periodicals; Polymerization -- Periodicals; 547.705
• DOI: 10.1039/d2py00351a
• Languages: English
• ISSNs: 1759-9954

Abstract

Abstract : A vanillin derivative containing β-hydroxy-amine functionalities was introduced into vitrimer materials using vinylogous urethane chemistry. These new materials have a high bio-based content and show fast reprocessability. Abstract : Research on bio-based covalent adaptable networks is popular nowadays in the search for an optimal implementation of thermoset materials and composites in a circular context. Herein, a vanillin derivative is integrated into vitrimers with promising material properties in which the vinylogous urethane associative chemistry has been used as a dynamic covalent chemistry platform. The vanillin derivative, 2-methoxyhydroquinone, is epoxidised and aminated by aqueous ammonia, with the formation of a bi-functional aromatic β-hydroxy-amine. The straightforward synthesis protocol is high yielding and up-scalable, without the need for any chromatographic purification step. The presented rigid, catalyst-free vitrimers have a high renewable carbon content (up to 86%), glass transition temperatures up to 80 °C and show very fast reprocessing and consequently a swift recyclability with relaxation times in the range of seconds by virtue of the applied β-hydroxy-amine functionality. This research thus provides a sustainable approach for the synthesis of vanillin-based vitrimers and fits in with growing interest for the design of recyclable crosslinked polymer materials.