Environmentally benign synthesis of vinyl ester resin from biowaste glycerin

Shah, Priyank N.; Kim, Nam-Joon; Huang, Zhuangrong; Jayamanna, Mahesh; Kokil, Akshay; Pine, Alex; Kaltsas, Jarmin; Jahngen, Edwin; Ryan, David K.; Yoon, Seongkyu; Kovar, Robert; Lee, Yong-Woo

doi:10.1039/c5ra03254g

Cited by 25 publications

(16 citation statements)

References 20 publications

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“…It is estimated that the materials with 20%–30% MMA contain around 7% of bioglycerol incorporated structurally. On the other hand, this amount would be higher ( ca 20%) if it is considered that GMA can be obtained from bioglycerol, as reported by Shah et al …”

Section: Resultsmentioning

confidence: 87%

Development of high‐modulus thermoset materials based on bioglycerol

Gómez

Echeverri

Inciarte

et al. 2019

Polymer International

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A high‐value application of crude bioglycerol in polymers was developed. In this application, bioglycerol was first transformed into a highly polyunsaturated resin (MAGLYMA) through maleinization–methacrylation reactions, under mild conditions (80–90 °C, 1–2 h). The resin was copolymerized with methyl methacrylate (MMA) (20%–50%) at room temperature over 8 h, affording rigid materials. The effect of MMA content on the mechanical and thermal properties was evaluated. The flexural modulus, flexural strength and surface hardness of the materials were around 3800 MPa, 130–180 MPa and 77 (Shore D), respectively. Tg values were in the range 92–105 °C. It is remarkable that excellent mechanical and thermal properties were obtained using a low concentration of MMA (20%). In particular, the mechanical properties of this material were better than those obtained for a commercial unsaturated polyester thermoset. © 2019 Society of Chemical Industry

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Section: Resultsmentioning

confidence: 87%

Development of high‐modulus thermoset materials based on bioglycerol

Gómez

Echeverri

Inciarte

et al. 2019

Polymer International

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“…Vanillin, an important natural resource with similar structure to styrene, has been most widely used in food processing, spices, drink, and curative. Lately, vanillin derivatives have been widely employed as renewable structural units for novel bio‐based polymers, chiefly due to vanillin is possible as a biological resource for the preparation of high performance materials and it can be extracted from lignin (the most abundant distributed raw materials, wood contains about 30%) mass production . Foreign countries have modified the reactive groups in the molecular structure of vanillin to produce a series of deep‐processed products, giving them various new characteristics and have been used in commercial production .…”

Section: Introductionmentioning

confidence: 99%

Thermosets resins prepared from soybean oil and lignin derivatives with high biocontent, superior thermal properties, and biodegradability

Chen

Hua²,

Wen

et al. 2019

J of Applied Polymer Sci

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A bio‐based monomer, methacrylated vanillyl alcohol (MVA), had been synthesized from vanillyl alcohol with methacrylate anhydride (MAA) via a solvent‐free, efficient method. The synthesis of MVA was confirmed by Fourier transform infrared (FTIR) and proton nuclear magnetic resonance (1H NMR). It was used to copolymerize with acrylated epoxidized soybean oil (AESO) to prepare a bio‐based resin (MVA–AESO). Excess MAA of MVA synthesis was further used to modify AESO with hydroxyl groups, generating (MVA–MAESO) with higher unsaturation degree. Their chemical structure and modification were characterized using 13C NMR and Fourier transform infrared analyses. Pure AESO and MVA resins were used to compare with MVA–AESO and MVA–MAESO in terms of their viscosity, curing performance, mechanical, and thermal properties. The synthesized MVA–AESO and MVA–MAESO resins showed much lower viscosities than pure AESO due to the dilution of MVA. In addition, the incorporation of MVA reduced curing temperatures, activation energies which caused MVA–AESO and MVA–MAESO had higher curing degree than pure AESO. With the combination of MVA and modification of MAA, flexible AESO networks exhibited superior flexural properties, storage modulus, glass‐transition temperature, and thermal stability. Furthermore, the biodegradation of the formulated bio‐based resins were also investigated. Results showed that the addition of monomer and the increase in the content of CC bonds did not significantly affect the biodegradability of AESO, which may be due to the fact that the degradable groups of AESO were not affected. This environmentally friendly, low (volatile organic) resin, prepared by a high efficiency and environmental protection synthetic route, can potentially replace typical petroleum‐based thermosets for the production environmentally friendly thermosetting resins. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2020, 137, 48827.

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“…On the other hand, an interesting strategy for obtain esters under milder conditions ( c . 70 °C) is the epoxy‐carboxyl reaction between carboxylic acids or phenols with suitable epoxides . In this route, the formation of esters occurs by opening the epoxide ring, generating isomers with pendant hydroxyl groups .…”

Section: Introductionmentioning

confidence: 99%

“…Specifically, methacrylated lauric acid led to a low VOC vinyl ester resins with low viscosity and high mechanical properties, using 10–20 wt% styrene. GMA is a versatile and reactive monomer which was synthesized recently using waste glycerol from biodiesel production . In that work, GMA from bioglycerol and bisphenol A were used as precursors for the synthesis of a vinyl ester resin through a novel environmentally benign protocol.…”

Section: Introductionmentioning

confidence: 99%

“…The synthesis of thermoset resins from glycerol usually involves prior derivatization via formation of esters (glycerolysis or esterification) at temperatures around 150-220 ∘ C. 12,13,18 On the other hand, an interesting strategy for obtain esters under milder conditions (c. 70 ∘ C) is the epoxy-carboxyl reaction between carboxylic acids or phenols with suitable epoxides. 20,21 In this route, the formation of esters occurs by opening the epoxide ring, generating isomers with pendant hydroxyl groups. 22,23 Tertiary amines or quaternary ammonium cations have been reported as highly active and selective catalysts for this reaction.…”

Section: Introductionmentioning

confidence: 99%

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Efficient processing of bioglycerol to a novel biobased polyunsaturated monomer

Gómez

Echeverri

Inciarte

et al. 2018

J of Chemical Tech & Biotech

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BACKGROUND Commercial synthesis of polyunsaturated monomers, like polyester resins, involves an energy‐demanding esterification process, which is usually carried out at 150–220 °C and long reaction times (>12 h). In addition, most of these monomers come from petrochemical sources and, therefore, are not renewable. In this research, a new polyunsaturated monomer was synthesized using crude glycerol from biodiesel production (bioglycerol), through an alternative and efficient process. RESULTS Bioglycerol was transformed to a polyunsaturated resin through maleinization and methacrylation reactions, under mild conditions (<100 °C and 2 h). The effects of temperature and molar ratio of reactants on these reactions were evaluated through a factorial design. The so‐obtained monomer was highly functionalized (5.05 double bonds per molecule) and negligible acid value (<2 mg KOH g−1). To assess its reactivity, the monomer was copolymerized with methyl methacrylate (MMA), affording a rigid material with excellent mechanical properties. In general, the properties were better than those obtained for commercial unsaturated polyester thermosets (flexural modulus, 3783.4 MPa; flexural strength, 161.5 MPa; surface hardness, 76 (Shore D) and Tg, 100.9 °C). This new monomer could also be suitable for the production of other polymers such as alkyd resins. CONCLUSION A new route to polyunsaturated monomers was developed from bioglycerol at relatively low temperatures, without solvents and with minimum intermediate purification stages. The monomer was suitable for reacting with MMA, affording a material with mechanical properties resembling those of a commercial unsaturated polyester thermoset. © 2018 Society of Chemical Industry

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Environmentally benign synthesis of vinyl ester resin from biowaste glycerin

Abstract: We present here for the first time a novel environmentally benign protocol for the synthesis of vinyl ester resin (VER).

Cited by 25 publications

References 20 publications

Development of high‐modulus thermoset materials based on bioglycerol

Development of high‐modulus thermoset materials based on bioglycerol

Thermosets resins prepared from soybean oil and lignin derivatives with high biocontent, superior thermal properties, and biodegradability

Efficient processing of bioglycerol to a novel biobased polyunsaturated monomer

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