Issue 5, 2023

Exploiting retro oxa-Michael chemistry in polymers

Abstract

One way to obtain recyclable polymeric materials is to include reversible bonds in polymers. Herein, we study the reversibility of the oxa-Michael reaction and explore its scope and limitations in simple model systems and further in linear polymers as well as in polymer networks. The results show that the retro oxa-Michael reaction of sulfone, acrylate or acrylonitrile based adducts is considerably fast at elevated temperatures (>100 °C) if Brønsted bases (e.g. KOH) are used as catalysts. Under these conditions, alcohols can easily be exchanged in oxa-Michael adducts within minutes. Furthermore, poly(ether)s derived from oxa-Michael reactions can be depolymerized into small fragments in the presence of alcohols and show self-healing characteristics in networks.

Graphical abstract: Exploiting retro oxa-Michael chemistry in polymers

Supplementary files

Article information

Article type
Paper
Submitted
22 okt 2022
Accepted
19 dec 2022
First published
04 jan 2023
This article is Open Access
Creative Commons BY-NC license

Polym. Chem., 2023,14, 651-661

Exploiting retro oxa-Michael chemistry in polymers

K. Ratzenböck, J. M. Uher, S. M. Fischer, D. Edinger, V. Schallert, E. Žagar, D. Pahovnik and C. Slugovc, Polym. Chem., 2023, 14, 651 DOI: 10.1039/D2PY01345B

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