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Preparation of Renewable Epoxy-Amine Resins With Tunable Thermo-Mechanical Properties, Wettability and Degradation Abilities From Lignocellulose- and Plant Oils-Derived Components

One-hundred percent renewable triphenol—GTF—(glycerol trihydroferulate) and novel bisphenols—GDF(x)–(glycerol dihydroferulate) were prepared from lignocellulose-derived ferulic acid and vegetal oil components (fatty acids and glycerol) using highly selective lipase-catalyzed transesterifications. Es...

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Detalles Bibliográficos
Autores principales: Hollande, Louis, Do Marcolino, Izia, Balaguer, Patrick, Domenek, Sandra, Gross, Richard A., Allais, Florent
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6445855/
https://www.ncbi.nlm.nih.gov/pubmed/30972325
http://dx.doi.org/10.3389/fchem.2019.00159
Descripción
Sumario:One-hundred percent renewable triphenol—GTF—(glycerol trihydroferulate) and novel bisphenols—GDF(x)–(glycerol dihydroferulate) were prepared from lignocellulose-derived ferulic acid and vegetal oil components (fatty acids and glycerol) using highly selective lipase-catalyzed transesterifications. Estrogenic activity tests revealed no endocrine disruption for GDF(x) bisphenols. Triethyl-benzyl-ammonium chloride (TEBAC) mediated glycidylation of all bis/triphenols, afforded innocuous bio-based epoxy precursors GDF(x)EPO and GTF-EPO. GDF(x)EPO were then cured with conventional and renewable diamines, and some of them in presence of GTF-EPO. Thermo-mechanical analyses (TGA, DSC, and DMA) and degradation studies in acidic aqueous solutions of the resulting epoxy-amine resins showed excellent thermal stabilities (T(d)5% = 282–310°C), glass transition temperatures (T(g)) ranging from 3 to 62°C, tunable tan α, and tunable degradability, respectively. It has been shown that the thermo-mechanical properties, wettability, and degradability of these epoxy-amine resins, can be finely tailored by judiciously selecting the diamine nature, the GTF-EPO content, and the fatty acid chain length.