High performance bio-based thermosets from dimethacrylated epoxidized sucrose soyate (DMESS)

Yu, Arvin Z.; Rahimi, Alireza; Webster, Dean C.

doi:10.1016/j.eurpolymj.2017.12.023

Cited by 24 publications

(14 citation statements)

References 44 publications

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“…From the DMTA curves (Figure ), 5 ( AVV ) closely matched the performance of styrene at 30% by weight diluents. The broad tan δ curves and presence of a second phase has been previously discussed in the literature. , …”

Section: Resultsmentioning

confidence: 99%

“…Motivated by a desire to innovate novel and practical solutions, some of our interest in sustainable thermosets has focused on utilizing epoxidized sucrose soyate (ESS) , and its methacrylated derivatives, including dimethacrylated epoxidized sucrose soyate (DMESS). − Notably, the high degree of functionality combined with rigid sucrose core impart high performance in terms of thermomechanical properties to DMESS-based thermosets as compared with traditional soybean oil derived resins. Vinyl ester resins in general are well-known for their robust performance in a variety of applications and are generally more reactive than unsaturated polyester resins due to the substitution pattern of the vinyl moiety .…”

Section: Introductionmentioning

confidence: 99%

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Renewable Reactive Diluents as Practical Styrene Replacements in Biobased Vinyl Ester Thermosets

Serum

Renner

et al. 2018

ACS Sustainable Chem. Eng.

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A concise series of renewable vinyl compounds has been prepared from benign biosourced precursors, vanillin and eugenol, in fair overall yield. These were evaluated against styrene as reactive diluents in a renewable high-performance vinyl ester resin thermoset: dimethacrylated-epoxidized-sucrose-soyate (DMESS). Each diluent contained a 1,2-dimethoxybenzene or veratrole core structure that connotes a decreased vapor pressure and thereby reduced exposure hazard. Viscosities for formulations (10, 20, and 30% by weight of diluents) with styrene and all three veratrole-diluents were evaluated. Veratrole-diluents were comparable to styrene at similar molar concentration. Thermosets formulated with 30% by weight of diluents were prepared and characterized by thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and dynamic mechanical thermal analysis (DMTA); the most promising thermoset was prepared using 3-allyl-1,2-dimethoxy-5-vinylbenzene-diluted-DMESS and closely matched the performance of the styrene-diluted thermoset in terms of thermal stability, glass transition temperature, toughness, and tensile strength.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Renewable Reactive Diluents as Practical Styrene Replacements in Biobased Vinyl Ester Thermosets

Serum

Renner

et al. 2018

ACS Sustainable Chem. Eng.

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“…2,3 Epoxides can be used in the synthesis of resins containing other reactive groups such as hydroxyls, cyclic carbonates or (meth)acrylates. [4][5][6] Additionally, the uses of epoxy and epoxy-derived resins extend to applications in areas such as electronic materials, biomedical systems and the aerospace industry. [7][8][9][10] Biobased resins derived from renewable resources are materials which have amassed a considerable interest.…”

Section: Introductionmentioning

confidence: 99%

“…Epoxy resins lead to a vast array of materials having desirable properties such as good overall mechanical properties, good adhesion to substrates, as well as heat and chemical resistance 2,3 . Epoxides can be used in the synthesis of resins containing other reactive groups such as hydroxyls, cyclic carbonates or (meth)acrylates 4–6 . Additionally, the uses of epoxy and epoxy‐derived resins extend to applications in areas such as electronic materials, biomedical systems and the aerospace industry 7–10 …”

Section: Introductionmentioning

confidence: 99%

Comparison of epoxidation methods for biobased oils: dioxirane intermediates generated from Oxone versus peracid derived from hydrogen peroxide

Setien

Ghasemi

Pourhashem

2021

Polymer International

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A study was carried out to compare the epoxidation of unsaturated vegetable oils using dioxirane intermediates generated in situ using Oxone to that by the peracid/hydrogen peroxide method. Epoxidized oils are typically synthesized using hydrogen peroxide, as well as acetic or formic acid. This synthesis requires heating and catalysts and generates acidic waste. Recently, advances have been made in the process of using Oxone (potassium peroxymonosulfate) and ketones to generate in situ dioxiranes to epoxidize alkenes. The dioxirane method allows for room temperature reactions and eliminates the use of peroxides and acids. Epoxidation of soybean oil, hempseed oil and sucrose soyate using in situ generated dioxiranes was carried out and parameters such as molar ratios and addition rates were studied. The data show that optimum reaction conditions are reached when molar ratios of Oxone and unsaturation are 1.6:1 and the Oxone addition rate is 1 mL min -1 . As a comparison, epoxidations using the acetic acid/hydrogen peroxide method were carried out and cured materials were prepared from the epoxidized compounds. Negligible differences were identified in the materials prepared from both synthetic pathways. An environmental sustainability assessment using green chemistry principles was also conducted for both methods to evaluate their safety and efficiency with respect to multiple criteria including minimizing waste generation and energy consumption. The analysis shows that, although the peracid method is atom economic and generates less waste, the dioxirane method offers better occupational safety and requires less energy, demonstrating the tradeoffs involved with either pathway if one is to be selected.

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“…Epoxidized vegetable oils and their derivatives have been recognized as potentially sustainable alternative sources with comparable properties to petroleum-based resins [ 3 ]. Among epoxidized vegetable oil-based resins, epoxidized sucrose soyate (ESS) has shown great potential as it and its derivatives have been shown to significantly enhance the mechanical properties of thermosets in a wide range of applications including composites [ 4 , 5 , 6 ]. A study of preparing a biocomposite from highly functional methacrylated epoxidized sucrose soyate and fiberglass fabric by Hosseini et al (2016) demonstrated that the produced biocomposite had excellent interfacial and mechanical properties [ 7 ].…”

Section: Introductionmentioning

confidence: 99%

A Preliminary Environmental Assessment of Epoxidized Sucrose Soyate (ESS)-Based Biocomposite

et al. 2020

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Biocomposites can be both environmentally and economically beneficial: during their life cycle they generally use and generate less petroleum-based carbon, and when produced from the byproduct of another industry or recycled back to the manufacturing process, they will bring additional economic benefits through contributing to a circular economy. Here we investigate and compare the environmental performance of a biocomposite composed of a soybean oil-based resin (epoxidized sucrose soyate) and flax-based reinforcement using life cycle assessment (LCA) methodology. We evaluate the main environmental impacts that are generated during the production of the bio-based resin used in the biocomposite, as well as the biocomposite itself. We compare the life cycle impacts of the proposed biocomposite to a functionally similar petroleum-based resin and flax fiber reinforced composite, to identify tradeoffs between the environmental performance of the two products. We demonstrate that the bio-based resin (epoxidized sucrose soyate) compared to a conventional (bisphenol A-based) resin shows lower negative environmental impacts in most studied categories. When comparing the biocomposite to the fossil fuel derived composite, it is demonstrated that using epoxidized sucrose soyate versus a bisphenol A (BPA)-based epoxy resin can improve the environmental performance of the composite in most categories except eutrophication and ozone layer depletion. For future designs, considering an alternative cross-linker to facilitate the bond between the bio-based resin and the flax fiber, may help improve the overall environmental performance of the biocomposite. An uncertainty analysis was also performed to evaluate the effect of variation in LCA model inputs on the environmental results for both the biocomposite and composite. The findings show a better overall carbon footprint for the biocomposite compared to the BPA-based composite at almost all times, demonstrating a good potential for marketability especially in the presence of incentives or regulations that address reducing the carbon intensity of products. This analysis allowed us to pinpoint hotspots in the biocomposite’s supply chain and recommend future modifications to improve the product’s sustainability.

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High performance bio-based thermosets from dimethacrylated epoxidized sucrose soyate (DMESS)

Cited by 24 publications

References 44 publications

Renewable Reactive Diluents as Practical Styrene Replacements in Biobased Vinyl Ester Thermosets

Renewable Reactive Diluents as Practical Styrene Replacements in Biobased Vinyl Ester Thermosets

Comparison of epoxidation methods for biobased oils: dioxirane intermediates generated from Oxone versus peracid derived from hydrogen peroxide

A Preliminary Environmental Assessment of Epoxidized Sucrose Soyate (ESS)-Based Biocomposite

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