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Sustainable design of vanillin-based vitrimers using vinylogous urethane chemistry

Stéphanie Engelen (UGent) , Aleksandra Alicja Wróblewska (UGent) , Kevin De Bruycker (UGent) , Resat Aksakal (UGent) , Vincent Ladmiral, Sylvain Caillol and Filip Du Prez (UGent)
(2022) POLYMER CHEMISTRY. 13(18). p.2665-2673
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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 beta-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 degrees C and show very fast reprocessing and consequently a swift recyclability with relaxation times in the range of seconds by virtue of the applied beta-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.
Keywords
RENEWABLE RESOURCES, HIGH-PERFORMANCE, EPOXY VITRIMER, NETWORKS, AMINES

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MLA
Engelen, Stéphanie, et al. “Sustainable Design of Vanillin-Based Vitrimers Using Vinylogous Urethane Chemistry.” POLYMER CHEMISTRY, vol. 13, no. 18, 2022, pp. 2665–73, doi:10.1039/d2py00351a.
APA
Engelen, S., Wróblewska, A. A., De Bruycker, K., Aksakal, R., Ladmiral, V., Caillol, S., & Du Prez, F. (2022). Sustainable design of vanillin-based vitrimers using vinylogous urethane chemistry. POLYMER CHEMISTRY, 13(18), 2665–2673. https://doi.org/10.1039/d2py00351a
Chicago author-date
Engelen, Stéphanie, Aleksandra Alicja Wróblewska, Kevin De Bruycker, Resat Aksakal, Vincent Ladmiral, Sylvain Caillol, and Filip Du Prez. 2022. “Sustainable Design of Vanillin-Based Vitrimers Using Vinylogous Urethane Chemistry.” POLYMER CHEMISTRY 13 (18): 2665–73. https://doi.org/10.1039/d2py00351a.
Chicago author-date (all authors)
Engelen, Stéphanie, Aleksandra Alicja Wróblewska, Kevin De Bruycker, Resat Aksakal, Vincent Ladmiral, Sylvain Caillol, and Filip Du Prez. 2022. “Sustainable Design of Vanillin-Based Vitrimers Using Vinylogous Urethane Chemistry.” POLYMER CHEMISTRY 13 (18): 2665–2673. doi:10.1039/d2py00351a.
Vancouver
1.
Engelen S, Wróblewska AA, De Bruycker K, Aksakal R, Ladmiral V, Caillol S, et al. Sustainable design of vanillin-based vitrimers using vinylogous urethane chemistry. POLYMER CHEMISTRY. 2022;13(18):2665–73.
IEEE
[1]
S. Engelen et al., “Sustainable design of vanillin-based vitrimers using vinylogous urethane chemistry,” POLYMER CHEMISTRY, vol. 13, no. 18, pp. 2665–2673, 2022.
@article{8758676,
  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 beta-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 degrees C and show very fast reprocessing and consequently a swift recyclability with relaxation times in the range of seconds by virtue of the applied beta-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.}},
  author       = {{Engelen, Stéphanie and Wróblewska, Aleksandra Alicja and De Bruycker, Kevin and Aksakal, Resat and Ladmiral, Vincent and Caillol, Sylvain and Du Prez, Filip}},
  issn         = {{1759-9954}},
  journal      = {{POLYMER CHEMISTRY}},
  keywords     = {{RENEWABLE RESOURCES,HIGH-PERFORMANCE,EPOXY VITRIMER,NETWORKS,AMINES}},
  language     = {{eng}},
  number       = {{18}},
  pages        = {{2665--2673}},
  title        = {{Sustainable design of vanillin-based vitrimers using vinylogous urethane chemistry}},
  url          = {{http://doi.org/10.1039/d2py00351a}},
  volume       = {{13}},
  year         = {{2022}},
}
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