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Thiol–Anhydride Dynamic Reversible Networks
Author(s) -
Podgórski Maciej,
Mavila Sudheendran,
Huang Sijia,
Spurgin Nathan,
Sinha Jasmine,
Bowman Christopher N.
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202001388
Subject(s) - succinic anhydride , phthalic anhydride , maleic anhydride , dynamic covalent chemistry , bifunctional , covalent bond , polymer chemistry , catalysis , elastomer , chemistry , materials science , maleimide , thiol , stress relaxation , reactivity (psychology) , organic chemistry , chemical engineering , copolymer , molecule , creep , polymer , composite material , medicine , supramolecular chemistry , alternative medicine , pathology , engineering
The reaction of thiols and anhydrides to form ring opened thioester/acids is shown to be highly reversible and it is accordingly employed in the fabrication of covalent adaptable networks (CANs) that possess tunable dynamic covalent chemistry. Maleic, succinic, and phthalic anhydride derivatives were used as bifunctional reactants in systems with varied stoichiometries, catalyst, and loadings. Dynamic characteristics such as temperature‐dependent stress relaxation, direct reprocessing and recycling abilities of a range of thiol–anhydride elastomers, glasses, composites and photopolymers are discussed. Depending on the catalyst strength, 100 % of externally imposed stresses were relaxed in the order of minutes to 2 hours at mild temperatures (80–120 °C). Pristine properties of the original materials were recovered following up to five cycles of a hot‐press reprocessing technique (1 h/100 °C).