Tara tannins as phenolic precursors of thermosetting epoxy resins

Aouf, Chahinez; Benyahya, Sofia; Esnouf, Antoine; Caillol, Sylvain; Boutevin, Bernard; Fulcrand, Hélène

doi:10.1016/j.eurpolymj.2014.03.034

Cited by 59 publications

(38 citation statements)

References 33 publications

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“…The reaction between FDCA and ECH to form BOFD proceeds through a mechanism similar to that recently reported by other authors for the acid moieties of vanillic and gallic acids [30][31][32] and represented in Scheme 1. The reaction proceeds through the addition of the carboxylate group of FDCA to the epoxy ring of ECH.…”

Section: 29mentioning

confidence: 63%

Green approaches in the synthesis of furan-based diepoxy monomers

et al. 2018

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Two eco-respectful, one-step synthetic routes for the preparation of a bio-based epoxy monomer derived from furan precursors are developed. The diglycidyl ester products are throughly characterized in terms of structure and thermal properties. Gathered results indicate that the two selected approaches allow the preparation of pure, furanic diglycidyl ester, which represents a viable bio-based alternative to its petrochemical aromatic counterpart.Research on bio-based polymers has been rapidly increasing in past years, pushed by growing environmental and economic concerns, as well as by the uncertainty about future availability of nite petrochemical resources.1 Sustainability is a keyword in this process. In this frame, products that are respectful towards the environment, including eco-compatible building blocks and additives, are now researched to replace petroleum-based polymers with those derived from naturally occurring feedstocks.2-4 In the eld of epoxy resins, this trend is related also to the necessity to nd a good candidate to substitute the controversial building block bisphenol A (BPA), a molecule recognized as an endocrine disrupter and reprotoxic substance.5 Epoxy resins are very versatile thermosetting polymers, extremely resistant to corrosion, moisture and chemicals, with good adhesive strength toward most materials (wettability) and low shrinkage upon curing. Due to their high glass transition temperatures and excellent mechanical strength, epoxy resins are widely employed in a broad range of applications, such as electronics, structural adhesives, aerospace composites and protective coatings. In the latter application, the use of BPA results in hazard for customers of food and beverage products packed into containers treated with epoxy resins. The effects of human body contamination caused by BPA are diabetes, cardiovascular diseases, altered liver enzymes and reproductive apparatus damages.5 For these reasons, this molecule has been banned in many countries for the manufacturing of child products, and in France and Canada from all the materials in direct contact with food. Therefore, the necessity to nd non-toxic and sustainable building blocks to replace BPA in the production of epoxy resins results mandatory. If one considers also the decreasing availability of oilderived feedstock, the research of new molecules is logically focusing on bio-derived chemicals. Epoxidized vegetable oils have been widely studied for their use in epoxy resins preparation, thanks to their characteristics, availability and low cost.6-8 Mechanical properties of epoxy resins obtained using these long aliphatic molecules, alone or mixed to aromatic epoxy comonomers, are encouraging.9,10 In order to further improve chemical, thermal and mechanical properties of epoxy resins, the presence of signicant content of aromatic moieties is required. In this frame, lignin derivatives appear to be the natural substitutes of BPA. However, time-and energyconsuming extraction processes make lignin-based epoxies expensive and b...

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Section: 29mentioning

confidence: 63%

Green approaches in the synthesis of furan-based diepoxy monomers

et al. 2018

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“…Recently, a handful of reports could be found in the literature on the subject of biobased aromatics for high-performance epoxy polymers. Some authors started directly from the raw resources such as lignin [9,10] or tannins [11,12]. This approach, however, suffers from several drawbacks such as structure complexity of the resource, issues with processability due to reactivity, high molecular weights and insolubility and composition variability depending on the species or the time of year.…”

Section: Introductionmentioning

confidence: 98%

Biobased epoxy thermosets from vanillin-derived oligomers

Fache¹,

Viola²,

Auvergne³

et al. 2015

European Polymer Journal

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125

101

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“…Peak CO overtones were observed in the 3500 cm −1 region but had low intensity in comparison to other peaks . The broad spectrum in the region 3000–3500 cm −1 indicated a hydroxyl group from tara tannin . Strong intensity peaks consisting of the carbonyl group from tara tannin, unsaturated ester (1730 cm −1 ), and polylactic acid, saturated aliphatic ester (1750 cm −1 ), appeared in the blend composite.…”

Section: Resultsmentioning

confidence: 98%

Tara tannin as active ingredient in electrospun fibrous delivery system

Sunthornvarabhas

Liengprayoon

Aouf

et al. 2016

J of Applied Polymer Sci

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This study evaluated the releasing performance of tara tannin, a cocktail of plant polyphenols, incorporated in submicron fiber, produced by the electrospinning process. Polylactic acid was used as a polymer matrix that carried two loading levels of tara tannin, 14.3 and 22.3% dry weight in the final product. The fiber diameter of composite fibers was in the range 500–700 nm. The release of tara tannin was controlled by material attachment as there was no evidence of chemical bonding between materials. This was further confirmed by FTIR and DSC. From the five combinations of acid that were presented in tara tannin, galloylquinic acid, with the smallest molecular weight composition, was released in the largest proportion (%molar) and exhibited antioxidant activity. This was confirmed by 2,2-diphenyl-1-picrylhydrazyl assay and HPLC-MS analyses. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016, 133, 43646. (Résumé d'auteur

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Tara tannins as phenolic precursors of thermosetting epoxy resins

Cited by 59 publications

References 33 publications

Green approaches in the synthesis of furan-based diepoxy monomers

Green approaches in the synthesis of furan-based diepoxy monomers

Biobased epoxy thermosets from vanillin-derived oligomers

Tara tannin as active ingredient in electrospun fibrous delivery system

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