Progress of Polymers from Renewable Resources: Furans, Vegetable Oils, and Polysaccharides

Gandini, Alessandro; Lacerda, Talita M.; Carvalho, Antônio J. F.; Trovatti, Eliane

doi:10.1021/acs.chemrev.5b00264

Cited by 636 publications

(487 citation statements)

References 275 publications

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“…The presence of non-conjugated C]C double bonds within these fatty acids are not sufficiently reactive to be polymerized directly. [13][14][15][16] Therefore, a series of polymerizable functional groups, such as epoxy, methacrylate, and acrylate groups may be introduced to convert soybean oil into thermosetting resins. Acrylated epoxidized soybean oil (AESO) and maleinated acrylated epoxidized soybean oil (MAESO) have been widely reported to replace petroleum-based vinyl ester resin or unsaturated polyester resin.…”

Section: Introductionmentioning

confidence: 99%

Bio-based reactive diluents as sustainable replacements for styrene in MAESO resin

Zhang

Thakur

et al. 2018

RSC Adv.

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Four different biorenewable methacrylated/acrylated monomers, namely, methacrylated fatty acid (MFA), methacrylated eugenol (ME), isobornyl methacrylate (IM), and isobornyl acrylate (IA) were employed as reactive diluents (RDs) to replace styrene (St) in a maleinated acrylated epoxidized soybean oil (MAESO) resin to produce bio-based thermosetting resins using free radical polymerization. The curing kinetics, gelation times, double bond conversions, thermal-mechanical properties, and thermal stabilities of MAESO-RD resin systems were characterized using DSC, rheometer, FT-IR, DMA, and TGA. The results indicate that all four RD monomers possess high bio-based carbon content (BBC) ranging from 63.2 to 76.9% and low volatilities (less than 7 wt% loss after being held isothermally at 30 C for 5 h). Moreover, the viscosity of the MAESO-RD systems can be tailored to acceptable levels to fit the requirements for liquid molding techniques. Because of the introduction of RDs to the MAESO resin, the reaction mixtures showed an improved reactivity and an accelerated reaction rate. FT-IR results showed that almost all the C]C double bonds within MAESO-RD systems were converted. The glass transition temperatures (T g ) of the MAESO-RDs ranged from 44.8 to 100.8 C, thus extending the range of application. More importantly, the T g of MAESO-ME resin (98.1 C) was comparable to that of MAESO-St resin (100.8 C).Overall, this work provided four potential RDs candidates to completely replace styrene in the MAESO resin, with the ME monomer being the most promising one.

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Section: Introductionmentioning

confidence: 99%

Bio-based reactive diluents as sustainable replacements for styrene in MAESO resin

Zhang

Thakur

et al. 2018

RSC Adv.

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“…In this line, furan derivatives [4] such as 5-hydroxymethylfurfural [5] or furfural [6] are respectively obtained from C6 or C5 sugar dehydrations [7] in the bio-refinery processes. These two compounds are among the most interesting biobased building blocks to design a sustainable chemistry [8] and they can further be transformed [9] in, for instance, 2,5-furandicarboxylic acid and furfuryl alcohol (FA) respectively. These latter compounds are indeed the two top of the class of biobased precursors used for their polymerization ability.…”

Section: Introductionmentioning

confidence: 99%

The FA Polymerization Disruption by Protic Polar Solvent

Falco¹,

Guigo²,

Vincent³

et al. 2018

Preprint

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Furfuryl alcohol (FA) is a biobased monomer derived from lignocellulosic biomass. The present work describes its polymerization in presence of protic polar solvents, i.e. water or isopropyl alcohol (IPA), using maleic anhydride (MA) as acidic initiator. The polymerization was followed from the liquid to the rubbery state by combining DSC and DMA data. In the liquid state, IPA disrupts the expected reactions during all the FA polymerization due to a stabilization of the furfuryl carbenium center. This causes the initiation of the polymerization at higher temperature, which is also reflected by higher activation energy. In water system, the MA opening allows to start the reaction at lower temperature. A higher pre-exponential factor value is obtained in that case. The DMA study of final branching reaction occurring in the rubbery state has highlighted continuous increase of elastic modulus until 290 °C. This increasing tendency of modulus was exploited to obtain activation energy dependences (Eα) of FA polymerization in the rubbery state.

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“…Vegetable oils are generating much interest as a feedstock for polymers, this is partly because they are environmentally friendly, have high purity, are annually renewable [2] and their relative ease of functionalization provides materials with useful thermal and mechanical properties [3][4][5][6][7][8][9][10][11][12][13][14]. Vegetable oils have also generated interest for their structure, with the commonest oils being triglycerides made mainly from five fatty acids; oleic (C18:1), linoleic (C18:2), linolenic (C18:3), stearic (C18:0) and palmitic (C16:0).…”

Section: Introductionmentioning

confidence: 99%

“…Vegetable oils have also generated interest for their structure, with the commonest oils being triglycerides made mainly from five fatty acids; oleic (C18:1), linoleic (C18:2), linolenic (C18:3), stearic (C18:0) and palmitic (C16:0). These oils, therefore containing varying amounts of carbon-carbon double bonds, which can easily be modified making them interesting from a chemical point of view [3][4][5][6][7][8][9][10][11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of Polyesters from Waste Grapeseed Oil: Comparison with Soybean and Rapeseed Oils

2016

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The aim of this study was to investigate the application of grapeseed oil, a waste product from the wine industry, as a renewable feedstock to make polyesters and to compare the properties of these materials with those derived from soybean and rapeseed oils. All three oils were epoxidized to give renewable epoxy monomers containing between 3.8 and 4.7 epoxides per molecule. Polymerisation was achieved with cyclic anhydrides catalysed by 4-methyl imidazole at 170 and 210°C. Polymers produced from methyl tetrahydrophthalic anhydride (Aradur917 Ò ) had greater tensile strength and Young's Modulus (tensile strength = 12.8 MPa, Young's Modulus = 1005 MPa for grapeseed) than methyl nadic anhydride (MNA) derived materials (5.6 and 468 MPa for grapeseed) due to increased volume of MNA decreasing crosslink density. Soybean and grapeseed oils produced materials with higher tensile strength (5.6-29.3 MPa) than rapeseed derived polyesters (2.5-3.9 MPa) due to a higher epoxide functionality increasing crosslinking. T g 's of the polyesters ranged from -36 to 62°C and mirrored the trend in epoxide functionality with grapeseed producing higher T g polymers (-17 to 17°C) than soybean (-25 to 6°C) and rapeseed (-36 to -27°C). Grapeseed oil showed similar properties to soybean oil in terms of T g , thermal degradation and Young's Modulus but produced polymers of lower tensile strength.Therefore grapeseed oil would only be a viable substitute for soybean for low stress applications or where thermal properties are more important.

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Progress of Polymers from Renewable Resources: Furans, Vegetable Oils, and Polysaccharides

Abstract: Scheme 6. Synthesis of Recyclable PBD via the DA/Retro-DA Reaction 55 Scheme 7. Synthesis of a Polyester and a Polyurethane Using a Diol Incorporating a DA Adduct

Cited by 636 publications

References 275 publications

Bio-based reactive diluents as sustainable replacements for styrene in MAESO resin

Bio-based reactive diluents as sustainable replacements for styrene in MAESO resin

The FA Polymerization Disruption by Protic Polar Solvent

Synthesis and Properties of Polyesters from Waste Grapeseed Oil: Comparison with Soybean and Rapeseed Oils

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