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Open AccessArticle

Synthesis of Pluri-Functional Amine Hardeners from Bio-Based Aromatic Aldehydes for Epoxy Amine Thermosets

1
Institut Charles Gerhardt, UMR 5253—CNRS, Université de Montpellier, Ecole Nationale Supérieure de Chimie de Montpellier, 240 Avenue Emile Jeanbrau, 34296 Montpellier, France
2
SAS Nouvelle Sogatra, 784 Chemin de la Caladette, 30350 Lezan, France
*
Author to whom correspondence should be addressed.
Academic Editor: Sylvain Caillol
Molecules 2019, 24(18), 3285; https://doi.org/10.3390/molecules24183285
Received: 23 July 2019 / Revised: 29 August 2019 / Accepted: 4 September 2019 / Published: 9 September 2019
(This article belongs to the Special Issue Natural Polymers and Biopolymers II)
Most of the current amine hardeners are petro-sourced and only a few studies have focused on the research of bio-based substitutes. Hence, in an eco-friendly context, our team proposed the design of bio-based amine monomers with aromatic structures. This work described the use of the reductive amination with imine intermediate in order to obtain bio-based pluri-functional amines exhibiting low viscosity. The effect of the nature of initial aldehyde reactant on the hardener properties was studied, as well as the reaction conditions. Then, these pluri-functional amines were added to petro-sourced (diglycidyl ether of bisphenol A, DGEBA) or bio-based (diglycidyl ether of vanillin alcohol, DGEVA) epoxy monomers to form thermosets by step growth polymerization. Due to their low viscosity, the epoxy-amine mixtures were easily homogenized and cured more rapidly compared to the use of more viscous hardeners (<0.6 Pa s at 22 °C). After curing, the thermo-mechanical properties of the epoxy thermosets were determined and compared. The isophthalatetetramine (IPTA) hardener, with a higher number of amine active H, led to thermosets with higher thermo-mechanical properties (glass transition temperatures (Tg and Tα) were around 95 °C for DGEBA-based thermosets against 60 °C for DGEVA-based thermosets) than materials from benzylamine (BDA) or furfurylamine (FDA) that contained less active hydrogens (Tg and Tα around 77 °C for DGEBA-based thermosets and Tg and Tα around 45 °C for DGEVA-based thermosets). By comparing to industrial hardener references, IPTA possesses six active hydrogens which obtain high cross-linked systems, similar to industrial references, and longer molecular length due to the presence of two alkyl chains, leading respectively to high mechanical strength with lower Tg. View Full-Text
Keywords: imine; epoxide; amine; thermoset; bio-based imine; epoxide; amine; thermoset; bio-based
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MDPI and ACS Style

Mora, A.-S.; Tayouo, R.; Boutevin, B.; David, G.; Caillol, S. Synthesis of Pluri-Functional Amine Hardeners from Bio-Based Aromatic Aldehydes for Epoxy Amine Thermosets. Molecules 2019, 24, 3285. https://doi.org/10.3390/molecules24183285

AMA Style

Mora A-S, Tayouo R, Boutevin B, David G, Caillol S. Synthesis of Pluri-Functional Amine Hardeners from Bio-Based Aromatic Aldehydes for Epoxy Amine Thermosets. Molecules. 2019; 24(18):3285. https://doi.org/10.3390/molecules24183285

Chicago/Turabian Style

Mora, Anne-Sophie; Tayouo, Russell; Boutevin, Bernard; David, Ghislain; Caillol, Sylvain. 2019. "Synthesis of Pluri-Functional Amine Hardeners from Bio-Based Aromatic Aldehydes for Epoxy Amine Thermosets" Molecules 24, no. 18: 3285. https://doi.org/10.3390/molecules24183285

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