Understanding the Effect of Side Reactions on the Recyclability of Furan–Maleimide Resins Based on Thermoreversible Diels–Alder Network

McReynolds, Brandon T.; Mojtabai, Kavon D.; Penners, Nicole; Kim, Gaeun; Lindholm, Samantha; Lee, Youngmin; McCoy, John D.; Chowdhury, Sanchari

doi:10.3390/polym15051106

Title: Understanding the Effect of Side Reactions on the Recyclability of Furan–Maleimide Resins Based on Thermoreversible Diels–Alder Network

Journal Article · Thu Feb 23 00:00:00 EST 2023 · Polymers

DOI:https://doi.org/10.3390/polym15051106· OSTI ID:1958322

; Mojtabai, Kavon D.; Penners, Nicole; Kim, Gaeun; Lindholm, Samantha;

;

; Chowdhury, Sanchari

We studied the effect of side reactions on the reversibility of epoxy with thermoreversible Diels–Alder (DA) cycloadducts based on furan and maleimide chemistry. The most common side reaction is the maleimide homopolymerization which introduces irreversible crosslinking in the network adversely affecting the recyclability. The main challenge is that the temperatures at which maleimide homopolymerization can occur are approximately the same as the temperatures at which retro-DA (rDA) reactions depolymerize the networks. Here we conducted detailed studies on three different strategies to minimize the effect of the side reaction. First, we controlled the ratio of maleimide to furan to reduce the concentration of maleimide groups which diminishes the effects of the side reaction. Second, we applied a radical-reaction inhibitor. Inclusion of hydroquinone, a known free radical scavenger, is found to retard the onset of the side reaction both in the temperature sweep and isothermal measurements. Finally, we employed a new trismaleimide precursor that has a lower maleimide concentration and reduces the rate of the side reaction. Our results provide insights into how to minimize formation of irreversible crosslinking by side reactions in reversible DA materials using maleimides, which is important for their application as novel self-healing, recyclable, and 3D-printable materials.

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Research Organization:: New Mexico Inst. of Mining and Technology, Socorro, NM (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0022261

OSTI ID:: 1958322

Alternate ID(s):: OSTI ID: 1962294

Journal Information:: Polymers, Journal Name: Polymers Vol. 15 Journal Issue: 5; ISSN 2073-4360

Publisher:: MDPI AGCopyright Statement

Country of Publication:: Switzerland

Language:: English

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36 MATERIALS SCIENCE
32 ENERGY CONSERVATION, CONSUMPTION, AND UTILIZATION
Diels–Alder reaction
furan
maleimide
recyclability
reversible
maleimide homopolymerization

Title: Understanding the Effect of Side Reactions on the Recyclability of Furan–Maleimide Resins Based on Thermoreversible Diels–Alder Network

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