Journal
MACROMOLECULES
Volume 54, Issue 18, Pages 8423-8434Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.macromol.1c01046
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Funding
- National Natural Science Foundation of China [52073296, 51773216]
- Research Project of Technology Application for Public Welfare of Ningbo City [202002N3091]
- Youth Innovation Promotion Association, CAS [2018335]
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The study designed catechol-based acetal CANs with accelerated acetal exchange through neighboring group participation (NGP). These CANs were prepared from bio-based epigallocatechin gallate (EGCG) and tri(ethylene glycol) divinyl ether (TEGVE) via one-step click cross-linking without catalysts. The dynamic covalent polymer networks showed excellent solvent resistance and mechanical properties due to dense cross-link density and high rigidity.
Covalent adaptable networks (CANS) represent a transition material combining favorable features of thermosets and thermoplastics. However, it is still a huge challenge to simultaneously achieve fast reprocessability and high performance for CANs. Here, we designed catechol-based acetal CANs to achieve continuous reprocessing without sacrificing thermal and mechanical properties. A small-molecule model study demonstrated the significantly accelerated acetal exchange by neighboring group participation (NGP) of phenolic hydroxyl. Using this internally catalyzed acetal chemistry, a series of CANs with a broad range of properties were simply prepared from bio-based epigallocatechin gallate (EGCG) and tri(ethylene glycol) divinyl ether (TEGVE) via one-step click cross-linking without using catalysts or releasing small-molecule byproducts. The dynamic nature of the CANs was confirmed via stress relaxation and multiple recycling methods including extrusion. While the dense cross-link density and high rigidity of the network provided high solvent resistance and mechanical properties. This work provides a promising and practical method to produce fast-reprocessing dynamic covalent polymer networks with dense cross-link density and superior performance.
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