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
Front. Chem. Sci. Eng. ›› 2021, Vol. 15 ›› Issue (2) : 330 -339.
Improved “cure on demand” of aromatic bismaleimide with thiol triggered by retro-Diels-Alder reaction
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 1H 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 1H 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).
thiol-ene polymerization / self-curing on demand / thia-michael addition / Diels-Alder / maleimide
Higher Education Press
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