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Peer-reviewedCC BY-NC 4.0Macromolecular Rapid Communications

A Chemically Recyclable 1,3,5‐Triazine‐Based Epoxy Thermoset Enabled by Nucleophilic Aromatic Substitution Reaction

  • Yi‐Ru Chen1,2
  • Fabian Eisenreich1,2
  • A. Catarina C. Esteves2,3
  • Željko Tomović1,2
  1. 1Polymer Performance Materials Group Department of Chemical Engineering and Chemistry & Institute for Complex Molecular Systems (ICMS) Eindhoven University of Technology Eindhoven The Netherlands
  2. 2Interactive Polymer Materials Research Center (IPM) Eindhoven University of Technology Eindhoven The Netherlands
  3. 3Laboratory of Physical Chemistry Department of Chemistry and Chemical Engineering & Institute for Complex Molecular Systems (ICMS) Eindhoven University of Technology Eindhoven The Netherlands
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Abstract

Developing recyclable thermosets without sacrificing structural integrity remains a significant hurdle in polymer circularity. In this study, we present a high‐performance, chemically recyclable epoxy thermoset based on 1,3,5‐triazine, demonstrating significant advancements in material recyclability and application potential. Utilizing liquid precursors, that is a trifunctional epoxy monomer (TOMTA) and a strategically selected secondary aromatic diamine hardener (MBMA), a cross‐linked network with a well‐defined architecture was produced under bulk conditions. The resulting thermoset exhibited exceptional thermal and mechanical properties as evidenced by a high glass transition temperature (Tg = 105°C), thermal stability (Td5% = 256°C), a Young's modulus of 3.0 GPa, and a tensile strength of 96 MPa, placing the material in the same performance range of conventional epoxy resins. Driven by an optimized binary K2CO3/TBD catalytic system in ethanol, the network underwent depolymerization enabled by a nucleophilic aromatic substitution reaction (SNAr), yielding the well‐defined building blocks TETA and the tetraol BDHPPM in 70% and 65%, respectively, via straightforward liquid‐liquid extraction. Re‐crosslinking these recovered building blocks regenerated the network, preserving nearly identical properties across multiple recycling cycles. The system was further applied as a debondable coating for glass. This 1,3,5‐triazine‐based network utilizing SNAr chemistry provides a robust route to high‐performance, recyclable epoxy thermosets.

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Cite

BibTeXRIS
BibTeX
@article{chen2026chemically,
  title = {{A Chemically Recyclable 1,3,5‐Triazine‐Based Epoxy Thermoset Enabled by Nucleophilic Aromatic Substitution Reaction}},
  author = {Yi‐Ru Chen and Fabian Eisenreich and A. Catarina C. Esteves and Željko Tomović},
  journal = {Macromolecular Rapid Communications},
  year = {2026},
  month = sep,
  doi = {10.1002/marc.70422},
  url = {https://doi.org/10.1002/marc.70422},
  note = {CC BY-NC 4.0},
}
RIS
TY  - JOUR
TI  - A Chemically Recyclable 1,3,5‐Triazine‐Based Epoxy Thermoset Enabled by Nucleophilic Aromatic Substitution Reaction
AU  - Yi‐Ru Chen
AU  - Fabian Eisenreich
AU  - A. Catarina C. Esteves
AU  - Željko Tomović
PY  - 2026
DA  - 2026/09/06
JO  - Macromolecular Rapid Communications
DO  - 10.1002/marc.70422
UR  - https://doi.org/10.1002/marc.70422
AB  - Developing recyclable thermosets without sacrificing structural integrity remains a significant hurdle in polymer circularity. In this study, we present a high‐performance, chemically recyclable epoxy thermoset based on 1,3,5‐triazine, demonstrating significant advancements in material recyclability and application potential. Utilizing liquid precursors, that is a trifunctional epoxy monomer (TOMTA) and a strategically selected secondary aromatic diamine hardener (MBMA), a cross‐linked network with a well‐defined architecture was produced under bulk conditions. The resulting thermoset exhibited exceptional thermal and mechanical properties as evidenced by a high glass transition temperature (Tg = 105°C), thermal stability (Td5% = 256°C), a Young's modulus of 3.0 GPa, and a tensile strength of 96 MPa, placing the material in the same performance range of conventional epoxy resins. Driven by an optimized binary K2CO3/TBD catalytic system in ethanol, the network underwent depolymerization enabled by a nucleophilic aromatic substitution reaction (SNAr), yielding the well‐defined building blocks TETA and the tetraol BDHPPM in 70% and 65%, respectively, via straightforward liquid‐liquid extraction. Re‐crosslinking these recovered building blocks regenerated the network, preserving nearly identical properties across multiple recycling cycles. The system was further applied as a debondable coating for glass. This 1,3,5‐triazine‐based network utilizing SNAr chemistry provides a robust route to high‐performance, recyclable epoxy thermosets.
SN  - 1022-1336
SN  - 1521-3927
ER  -