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Open AccessArticle

Acetoacetate Based Thermosets Prepared by Dual-Michael Addition Reactions

1
Thermodynamics Laboratory, ETSEIB, Universitat Politècnica de Catalunya, Av. Diagonal 647, 08028 Barcelona, Spain
2
Department of Analytical and Organic Chemistry, Universitat Rovira i Virgili, C/Marcel lí Domingo s/n, 43007 Tarragona, Spain
*
Author to whom correspondence should be addressed.
Polymers 2019, 11(9), 1408; https://doi.org/10.3390/polym11091408
Received: 13 May 2019 / Revised: 31 July 2019 / Accepted: 1 August 2019 / Published: 27 August 2019
(This article belongs to the Special Issue Thermosets II)
A novel set of dual-curable multiacetoacetate-multiacrylate-divinyl sulfone ternary materials with versatile and manipulable properties are presented. In contrast to common dual-curing systems, the first stage polymer herein consists of a densely crosslinked, high Tg network as a result of base-catalyzed multiacetoacetate-divinyl sulfone Michael addition. A more flexible secondary network forms after base-catalyzed Michael addition of remaining multiacetoacetate to multiacrylate. Curing is truly sequential as the rates of the two Michael additions are significantly different. Curing kinetics were analyzed using differential scanning calorimetry (DSC) and Fourier-transform infrared (FTIR). The materials at each curing stage were characterized using dynamic mechanical analysis (DMA) and SEM. Although some phase separation was observed in certain formulations, the incompatibilities were minimized when the molar percentage of the acetoacetate-divinyl sulfone polymer network was above 75%. Furthermore, the environmental scanning electron microscopy (ESEM) images of these materials show that the more flexible acetoacetate-acrylate phase is dispersed in the form of polymeric spheres within the rigid acetoacetate-divinyl sulfone matrix. This unique dual microstructure can potentially render these materials highly resilient in applications requiring densely crosslinked polymer architectures with enhanced toughness. View Full-Text
Keywords: dual-curing; Michael addition; click chemistry; acetoacetate; divinyl sulfone; acrylate dual-curing; Michael addition; click chemistry; acetoacetate; divinyl sulfone; acrylate
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MDPI and ACS Style

Konuray, O.; Fernández-Francos, X.; Ramis, X.; Serra, À. Acetoacetate Based Thermosets Prepared by Dual-Michael Addition Reactions. Polymers 2019, 11, 1408. https://doi.org/10.3390/polym11091408

AMA Style

Konuray O, Fernández-Francos X, Ramis X, Serra À. Acetoacetate Based Thermosets Prepared by Dual-Michael Addition Reactions. Polymers. 2019; 11(9):1408. https://doi.org/10.3390/polym11091408

Chicago/Turabian Style

Konuray, Osman; Fernández-Francos, Xavier; Ramis, Xavier; Serra, Àngels. 2019. "Acetoacetate Based Thermosets Prepared by Dual-Michael Addition Reactions" Polymers 11, no. 9: 1408. https://doi.org/10.3390/polym11091408

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