Issue 14, 2022

Combining vinylogous urethane and β-amino ester chemistry for dynamic material design

Abstract

This study combines vinylogous urethane (VU) and β-amino ester chemistry for the synthesis of covalent adaptable networks (CANs). The resulting CANs are synthesised using a range of diacetoacetates and commercially available diacrylates along with tris(2-aminoethyl)amine, which functions as both amine and crosslinker. The CANs are extensively analysed to determine both their thermal and rheological properties. Several re-processable elastomeric materials are obtained, thanks to the use of polypropylene glycol-containing diacetoacetates of varying molecular weights and are analysed in more detail and compared with VU and amino-ester reference materials. Frequency sweep measurements show no noticeable drop in storage modulus of these CANs between 100–180 °C, indicating a maintained crosslink density. The elastomeric CANs are recycled multiple times, exhibiting no clear loss of dynamic behaviour or any obvious side-reactions.

Graphical abstract: Combining vinylogous urethane and β-amino ester chemistry for dynamic material design

Supplementary files

Article information

Article type
Paper
Submitted
07 janv. 2022
Accepted
11 mars 2022
First published
17 mars 2022

Polym. Chem., 2022,13, 2008-2018

Combining vinylogous urethane and β-amino ester chemistry for dynamic material design

J. O. Holloway, C. Taplan and F. E. Du Prez, Polym. Chem., 2022, 13, 2008 DOI: 10.1039/D2PY00026A

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