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

Abstract

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.

Synthesis of Lactic Acid-Based Thermosetting Resins and Their Ageing and Biodegradability

“…Soil burial tests were done for three months. It was concluded that the resins had good biodegradability [28]. Chow, Tan and Ahmad prepared a bio-based thermoset resin by crosslinking an epoxidized soybean oil with an organic anhydride as a curing agent.…”

High biorenewable content acrylate photocurable resins for DLP 3D printing

“…Biodegradability of soybean oil‐based polymers could be predicted due to biodegradable triglyceride moieties, 36 through various RDs, cross‐linkers, and additives change the structure and density of cross‐links and affect biodegradability of polymers. About 15%–16% of thermally cross‐linked AESO and vanillin dimethacrylate thermosets degraded after a 3‐month soil burial test 37 . About 25% of 50% AESO blends with polyurethane acrylate biodegraded in the presence of the soft‐rot fungus Chaetomium globosum after 130 days of exposure, 38 while only about 6% of poly(ethylene glycol) diacrylate photocross‐linked with the same amount of AESO degraded in 24 days in phosphate buffer solution 39 .…”

“…About 15%-16% of thermally cross-linked AESO and vanillin dimethacrylate thermosets degraded after a 3-month soil burial test. 37 About 25% of 50% AESO blends with polyurethane acrylate biodegraded in the presence of the soft-rot fungus Chaetomium globosum after 130 days of exposure, 38 while only about 6% of poly(ethylene glycol) diacrylate photocross-linked with the same amount of AESO degraded in 24 days in phosphate buffer solution. 39 These moderate differences in the biodegradability of AESO-based polymers indicate not only the huge effect of comonomer, but also the type of the test used for determination of biodegradability on the obtained results.…”

The Prospering of Macromolecular Materials Based on Plant Oils within the Blooming Field of Polymers from Renewable Resources

“…Epoxidation is another suitable preliminary reaction for the insertion of acrylic moieties into the triglyceride backbone, which was the route adopted to prepare acrylated linseed oil and, in a further step, aza-Michael polymers using priamine 1071, amine-terminated poly(propyleneoxide)s (jeffamines), and meta-xylylenediamine as crosslinkers [ 45 ]. In a similar vein, acrylated epoxidized soybean oil was copolymerized with methacrylated vanillyl alcohol, which had been synthesized from vanillyl alcohol and methacrylate anhydride, to produce thermoset resins [ 46 ].…”