Covalent Adaptable Networks Using β-Amino Esters as Thermally Reversible Building Blocks.

Journal of the American Chemical Society
Christian TaplanFilip E Du Prez

Abstract

In this study, β-amino esters, prepared by the aza-Michael addition of an amine to an acrylate moiety, are investigated as building blocks for the formation of dynamic covalent networks. While such amino esters are usually considered as thermally nondynamic adducts, the kinetic model studies presented here show that dynamic covalent exchange occurs via both dynamic aza-Michael reaction and catalyst-free transesterification. This knowledge is transferred to create β-amino ester-based covalent adaptable networks (CANs) with coexisting dissociative and associative covalent dynamic exchange reactions. The ease, robustness, and versatility of this chemistry are demonstrated by using a variety of readily available multifunctional acrylates and amines. The presented CANs are reprocessed via either a dynamic aza-Michael reaction or a catalyst-free transesterification in the presence of hydroxyl moieties. This results in reprocessable, densely cross-linked materials with a glass transition temperature (Tg) ranging from -60 to 90 °C. Moreover, even for the low Tg materials, a high creep resistance was demonstrated at elevated temperatures up to 80 °C. When additional β-hydroxyl group-containing building blocks are applied during the netw...Continue Reading

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Oct 29, 2020·Chemical Society Reviews·Filip Van LijsebettenFilip E Du Prez
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Dec 29, 2020·Macromolecular Rapid Communications·Christian TaplanFilip E Du Prez
Apr 16, 2020·Chemical Science·Marc GuerreFilip E Du Prez

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Citations

Sep 16, 2021·Journal of the American Chemical Society·Filip Van LijsebettenFilip E Du Prez

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