Royal College of Surgeons in Ireland
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Cleavable epoxy networks using azomethine-bearing amine hardeners

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journal contribution
posted on 2023-05-17, 15:46 authored by Angeliki Chanteli, Marcus Ó Conaire, Ruairi Brannigan, Andreas HeiseAndreas Heise, Paul M. Weaver, Ioannis Manolakis
This work is a proof-of-concept of the use of azomethine-bearing diamines as novel hardeners of standard epoxy compounds to yield cleavable and thermoformable covalent adaptable networks (CANs), with functional properties otherwise comparable to conventional epoxy networks. A suitable aromatic diamine (TPA-o-PD) was synthesised at acceptable purity for the intended use and successfully reacted with DGEBA. The resulting azomethine-bearing cured epoxy networks exhibited glass transition temperature values and a thermal stability profile similar to conventional epoxy network counterparts. In contrast to their conventional counterparts however, the azomethine-bearing networks were shown to dissolve in mixtures of chloroform and methanesulfonic acid, due to acid hydrolysis of at least some of the azomethine bonds of the network. The resulting recyclate material after evaporating the solvent was consistent with the profile of a thermoplastic polymer of high molecular weight, suggesting limited depolymerisation/network cleavage during dissolution in the chloroform/methanesulfonic acid mixture. The recyclates were soluble in polar aprotic solvents and showed good thermal stability, high Tg and molecular weight values, consistent with the attributes of engineering thermoplastics. Lastly, the cured networks were shown to be thermoformable at 200 °C, yielding self-standing films with only minor reduction of properties.


Science Foundation Ireland: Future Innovator Prize - Plastics Challenge 2020, project r 2 -Epoxy (Recyclable and reworkable epoxy resins systems, ref. 20/FIP/PL/8426).



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Published Citation

Chanteli A, Conaire MÓ, Brannigan R, Heise A, Weaver PM, Manolakis I. Cleavable epoxy networks using azomethine-bearing amine hardeners. Reactive and Functional Polymers. 2022;178:105338.

Publication Date

8 July 2022


  • Chemistry

Research Area

  • Chemistry and Pharmaceutical Sciences
  • Biomaterials and Regenerative Medicine


Elsevier BV


  • Published Version (Version of Record)