Issue 47, 2022

Biobased catalyst-free covalent adaptable networks based on CF3-activated synergistic aza-Michael exchange and transesterification

Abstract

Recently, fluorine neighboring group activation emerged as a new way of promoting acid–epoxy reaction and transesterification in vitrimer materials. Pursuing this idea, the effect of a CF3 group on aza-Michael addition and aza-Michael exchange was examined and confirmed on model molecules. Following these positive results, a CAN incorporating aza-Michael bonds and CF3-activated ester functions was synthesized and compared to analogous materials deprived of any CF3 groups on the one hand, or of any hydroxyl groups on the other hand. The study of the mechanical properties of these materials highlighted the synergistic effect of the two exchange reactions and the accelerating effect of the fluorinated group. The fluorinated and hydroxylated material was shown to be reprocessable at 100 °C in 1 h under 3 tons whereas the fluorinated only and the hydroxylated only materials were respectively reprocessed at 120 °C and 150 °C. These catalyst-free CANs were synthesized from natural resources further enhancing the sustainability of these materials. This study demonstrates the potential of biobased CANs featuring fluorinated esters as low environmental impact and easily reprocessable materials.

Graphical abstract: Biobased catalyst-free covalent adaptable networks based on CF3-activated synergistic aza-Michael exchange and transesterification

Supplementary files

Article information

Article type
Paper
Submitted
26 Jūn. 2022
Accepted
26 Sept. 2022
First published
26 Sept. 2022
This article is Open Access
Creative Commons BY-NC license

J. Mater. Chem. A, 2022,10, 25085-25097

Biobased catalyst-free covalent adaptable networks based on CF3-activated synergistic aza-Michael exchange and transesterification

D. Berne, B. Quienne, S. Caillol, E. Leclerc and V. Ladmiral, J. Mater. Chem. A, 2022, 10, 25085 DOI: 10.1039/D2TA05067F

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements