Biobased epoxy thermosets from vanillin-derived oligomers

Fache, Maxence; Viola, Arnaud; Auvergne, Rémi; Boutevin, Bernard; Caillol, Sylvain

doi:10.1016/j.eurpolymj.2015.03.048

Cited by 126 publications

(104 citation statements)

References 27 publications

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“…However, it was only estimated in the case of the mixture of Gtype phenolics and could not be determined for the mixture of GS-type phenolics. In a previous paper 44 Table 4. The Epoxide Equivalent Weight (EEW) is a value commonly used in industry and represents the mass of mixture accounting for 1 mole of epoxide groups.…”

Section: H Nmr Epoxy Titrationmentioning

confidence: 98%

“…Precedent works demonstrated the potential of the use of vanillin to prepare renewable polymers, 13, 41 especially epoxy thermosets. [42][43][44] Why not use the unrefined mixture of phenolics available from lignin-to-vanillin processes (Table 1) to prepare epoxy polymers? By-passing the difficult purification steps would hold many advantages -both economic and environmental -such as reduced use of acids and solvents, reduced energy consumption, increased productivity, etc.…”

Section: Insert Scheme 2 Single Columnmentioning

confidence: 99%

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Epoxy thermosets from model mixtures of the lignin-to-vanillin process

2016

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Section: H Nmr Epoxy Titrationmentioning

confidence: 98%

Section: Insert Scheme 2 Single Columnmentioning

confidence: 99%

Epoxy thermosets from model mixtures of the lignin-to-vanillin process

2016

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“…The monomer approach toward renewable based epoxy thermosets from lignin‐obtained phenols was already intensively investigated. Vanillin‐based epoxy thermosets were described in detail by Caillol and co‐workers . Recently, epoxy thermosets from glycidylated iso‐eugenol were presented .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Epoxy Thermosetting Polymers from Glycidylated Organosolv Lignin and Bisphenol A

Over

Grau

Grelier

et al. 2016

Macromol. Chem. Phys.

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Diglycidylether of bisphenol A and isophorone diamine (IPDA) are industrially used for polyepoxide curing. Herein, glycidylated Organosolv lignin (GOL) is cured with diglycidyl ether of bisphenol A and IPDA for intensive studies. Organosolv lignin (OL) is therefore first glycidylated with epichlorohydrin to a material with an epoxy content of 3.2 mmol g–1 and analyzed via FT‐IR, 1H and 31P NMR. Epoxy thermosets with up to 42 wt% GOL are cured in differential scanning calorimetry (DSC) crucibles, analyzing the residual reaction heat. Characterization of dog bone shaped specimens is described with regard to structural properties from scanning electron microscopy and FT‐IR, thermal properties by DSC and thermogravimetric analysis, as well as mechanical properties by dynamic mechanical analysis and stress/strain measurements. A lignin content between 8% and 33% leads to higher crosslinking density, resulting in a higher glass transition, lower swelling percentage, and increased stiffness (Young's modulus) if compared to non‐GOL polymers.

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“…However, industrially, epoxy resins are produced from DGEBA‐based oligomers, which allow a better processability and control of the thermomechanical properties. Following this trend, Caillol and co‐workers prepared epoxy oligomers ( 15 ) from 11 and 14 , in different ratios, by the industrially used “fusion” process with triphenylbutylphosphonium bromide . By tuning the length of the oligomers, the cross‐linking density of the resulting material is affected, thus enabling the researchers to formulate epoxy resins with T g s ranging from 80 to 110 °C.…”

Section: Thermoset Polymersmentioning

confidence: 99%

From Lignin‐derived Aromatic Compounds to Novel Biobased Polymers

Llevot

Grau

Carlotti

et al. 2015

Macromol. Rapid Commun.

326

227

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Nowadays, the synthesis of (semi)aromatic polymers from lignin derivatives is of major interest, as aromatic compounds are key intermediates in the manufacture of polymers and lignin is the main source of aromatic biobased substrates. Phenols with a variety of chemical structures can be obtained from lignin deconstruction; among them, vanillin and ferulic acid are the main ones. Depending on the phenol substrates, different chemical modifications and polymerization pathways are developed, leading to (semi)aromatic polymers covering a wide range of thermomechanical properties. This review discusses the synthesis and properties of thermosets (vinyl ester resins, cyanate ester, epoxy, and benzoxazine resins) and thermoplastic polymers (polyesters, polyanhydrides, Schiff base polymers, polyacetals, polyoxalates, polycarbonates, acrylate polymers) prepared from vanillin, ferulic acid, guaiacol, syringaldehyde, or 4-hydroxybenzoic acid.

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Biobased epoxy thermosets from vanillin-derived oligomers

Cited by 126 publications

References 27 publications

Epoxy thermosets from model mixtures of the lignin-to-vanillin process

Epoxy thermosets from model mixtures of the lignin-to-vanillin process

Synthesis and Characterization of Epoxy Thermosetting Polymers from Glycidylated Organosolv Lignin and Bisphenol A

From Lignin‐derived Aromatic Compounds to Novel Biobased Polymers

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