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Journal Article 1

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2021 1

Keywords

Diels-Alder 1

maleimide 1

self-curing on demand 1

thia-michael addition 1

thiol-ene polymerization 1

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

Vincent Froidevaux, Mélanie Decostanzi, Abdelatif Manseri, Sylvain Caillol, Bernard Boutevin, Rémi Auvergne

Frontiers of Chemical Science and Engineering 2021, Volume 15, Issue 2,   Pages 330-339 doi: 10.1007/s11705-020-1929-6

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).

Keywords: thiol-ene polymerization     self-curing on demand     thia-michael addition     Diels-Alder     maleimide    

Title Author Date Type Operation

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

Vincent Froidevaux, Mélanie Decostanzi, Abdelatif Manseri, Sylvain Caillol, Bernard Boutevin, Rémi Auvergne

Journal Article