New ultrastiff bio-furan epoxy networks with high Tg: Facile synthesis to excellent properties

Meng, Jingjing; Zeng, Yushun; Chen, Pengfei; Zhang, Jie; Yang, Cheng; Fang, Zheng; Guo, Kai

doi:10.1016/j.eurpolymj.2019.109292

Cited by 33 publications

(36 citation statements)

References 38 publications

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“…The catalyst worked also for substrates having a heteroaromatic ring, affording glycidyl 2-pyiridinecarboxylic acid (6e) and glycidyl 2-thiophenecarboxylic acid (6f) in moderate yields (6e: 73%, 6f: 61%). Moreover, methyl 2-furancarboxylate (5g) and dimethyl 2,5-furancarboxylate (5h), which are useful biomassderived substrates, [38][39][40][41][42] are also accessible through this approach: glycidyl esters 6g and 6h were isolated in good to moderate yields (6g: 80%, 6h: 71%). Overall, a wide scope of value-added glycidyl esters is accessible using 3-Cl.…”

Section: Resultsmentioning

confidence: 99%

DNP NMR spectroscopy enabled direct characterization of polystyrene-supported catalyst species for synthesis of glycidyl esters by transesterification

et al. 2022

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Section: Resultsmentioning

confidence: 99%

DNP NMR spectroscopy enabled direct characterization of polystyrene-supported catalyst species for synthesis of glycidyl esters by transesterification

et al. 2022

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“…Guo's team 98 reported the quasi same synthesis but these authors substituted DDM by 33 and 44 DDS (Figure 9) to yield epoxy resins, the thermal and mechanical properties of which are listed in Table 6. Although the Tg value of the material obtained from B is quite high, that from DGEBA achieved with the same hardener is even higher (237 °C).…”

Section: -Diglycidyl Ester Of 25-furandicarboxylic Acid (B)mentioning

confidence: 99%

Synthesis and Properties of Furan Derivatives for Epoxy Resins

Eid

Améduri

Boutevin

2021

ACS Sustainable Chem. Eng.

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The discovery of huge petroleum reserves in the 19th century was a golden opportunity that promoted the industrial revolution, by offering a wide variety of cheap raw materials and a reliable source of energy. This caused an unprecedented increase of commodity and production of specialty chemicals in order to fulfill the needs of the global markets. However, as the global warming and the environmental issues has become a hazardous and worried situation, researchers are looking for bio renewable monomers with low toxicity in order to produce more sustainable polymers. This policy was also applied to epoxy resin materials because of their high volume production in industry for a wide range of applications. This review highlights the recent advances in the preparation of diamines and diepoxy monomers for the synthesis of epoxy resins, mainly from 2-furfural, 5-(hydroxymethyl)furfural (5-HMF), and 2,5-furandicarboxylic acid (FDCA), obtained from natural cellulose and hemicellulose feedstocks, respectively, and able to replace phthalic moieties in polyethylene terephthalate. In addition, the processes involved in the monomers preparation, such as reductive amination, etherification, esterification and carbonatation are listed. This review, reporting quasi-exhaustive synthetic pathways of epoxy precursors containing furanic moieties and describing the resulting resins, is composed of seven main parts, based on the synthesis of glycidyl derivatives containing one or two or four furan nuclei bearing or not a spacer between the furan ring and the function. The influence of the substituents on furan moieties (O, CO, CH 2 ) and the spacer between these groups have also been evaluated. Finally, thermal and a few mechanical properties of the obtained bio-sourced epoxy resins were compared to their fossil fuel analogues (from bisphenol A), featuring the high potential of bio-based monomers as substituents for non-renewable ones.

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“…5-Hydroxymethylfurfural (HMF) is a promising biomass-derived compound with great potential for the synthesis of biofuels, polymers, solvents, pharmaceuticals, and other useful molecules. , In the area of polymer synthesis, the glycidyl ester of furan dicarboxylic acid (FDCA) has been synthesized and thermosets were made with different curing chemistries. , The glycidyl ester of FDCA has also been reacted with methacrylic acid to form dimethacrylate, and thermosets were made by thermal free radical polymerization . The dimethacrylate of bis-hydroxymethyl furan was synthesized and used as a monomer to prepare polymeric materials via proton-transfer polymerization .…”

Section: Introductionmentioning

confidence: 99%

Bio-Based Furanic Di(meth)acrylates as Reactive Diluents for UV Curable Coatings: Synthesis and Coating Evaluation

Qian

Sutton

et al. 2021

ACS Sustainable Chem. Eng.

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A series of photocurable di(meth)acrylates from asymmetric and symmetric furan-based diols were prepared in good yields and evaluated for use as reactive diluents in UVcurable coatings. The furan-based di(meth)acrylates were found to have viscosities of ca. 9−91 mPa•s at 20 °C and were used as reactive diluents with a commonly used urethane acrylate resin to prepare photopolymerizable coating systems. The coating formulations were cured using UV light, and properties such as solvent resistance, hardness, impact strength, and adhesion were evaluated. The thermal properties of the coatings were characterized using differential scanning calorimetry and thermogravimetric analysis. Dynamic mechanical analysis was used to determine the viscoelastic properties of the coatings. Nanoindentation experiments were performed to evaluate the modulus of elasticity and hardness of the coatings. In general, the coatings containing the furan-based (meth)acrylates had high hardness, elastic modulus, and glass transition temperature.

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New ultrastiff bio-furan epoxy networks with high Tg: Facile synthesis to excellent properties

Cited by 33 publications

References 38 publications

DNP NMR spectroscopy enabled direct characterization of polystyrene-supported catalyst species for synthesis of glycidyl esters by transesterification

DNP NMR spectroscopy enabled direct characterization of polystyrene-supported catalyst species for synthesis of glycidyl esters by transesterification

Synthesis and Properties of Furan Derivatives for Epoxy Resins

Bio-Based Furanic Di(meth)acrylates as Reactive Diluents for UV Curable Coatings: Synthesis and Coating Evaluation

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