Organic chemistry

Covalent bond

Polymer chemistry

Maleimide

Elastomer

Dynamic covalent chemistry

Creep

Engineering

Catalysis

Copolymer

Composite material

Stress relaxation

Chemistry

Materials science

Maleic anhydride

Phthalic anhydride

Succinic anhydride

Thiol

Molecule

Bifunctional

Supramolecular chemistry

Chemical engineering

Polymer

Angewandte Chemie International Edition

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).

Thiol–Anhydride Dynamic Reversible Networks