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.