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Frontiers of Chemical Science and Engineering >> 2021, Volume 15, Issue 2 doi: 10.1007/s11705-020-1929-6

Improved “cure on demand” of aromatic bismaleimide with thiol triggered by retro-Diels-Alder reaction

Institut Charles Gerhardt Montpellier, UMR 5253-CNRS, Université de Montpellier, ENSCM, 34296 Montpellier Cedex 5, France

Received: 2020-07-10 Accepted: 2020-09-10 Available online: 2020-09-10

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Abstract

This study focuses on the synthesis of new liquid aromatic bismaleimide monomers in order to improve self-curing on demand (SCOD) systems previously based on aliphatic bismaleimides. These SCOD systems are based on Diels-Alder (DA)/retro-DA reactions. The syntheses of new different aromatic bismaleimides with ester and amide bonds are presented. These maleimides have been protected using DA reaction and characterized by H NMR analysis to determine protection rate and diastereomer ratios. The retro-DA reactions of both aromatic and aliphatic DA adducts in presence of thiol molecules were studied. Kinetic analysis was monitored by H NMR and compared to model study. Finally, both aromatic and aliphatic bismaleimides-based polymers were synthesized with 2-mercaptoethyl ether and thermal properties of polymers were compared. The glass transition temperature values ranged from –20 °C to 14 °C and very good thermal stabilities were observed (up to 300 °C).

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