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Cleavable epoxy networks using azomethine-bearing amine hardeners

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journal contribution
posted on 2023-02-08, 10:04 authored by Angeliki ChanteliAngeliki Chanteli, Marcus O Conaíre, Ruairi Brannigan, Andreas Heise, PAUL WEAVERPAUL 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.  


Recyclable & Re-Processable Epoxy Resin Systems (r2-Epoxy)

Science Foundation Ireland

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Reactive and Functional Polymers 178, 105338



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