Tsujimoto, T., Takayama, T., & Uyama, H. (2015). Polymers, 7(10), 2165-2174.
This paper presents the synthesis of plant oil-based shape memory materials using epoxidized soybean oil (ESO) and polycaprolactone (PCL). PolyESO/PCL was synthesized through acid-catalyzed curing in the presence of PCL. The polyESO/PCL exhibited excellent shape memory properties, with shape recovery behavior that can be repeatedly implemented. This polyESO/PCL material shows promise for contributing to the development of biodegradable smart materials.
Synthesis of PolyESO/PCL: The synthesis of polyESO/PCL is as follows. ESO (0.5 g) and PCL (0.5 g) were dissolved in 2.5 mL of chloroform, and a thermal latent cationic catalyst was added to the solution. The solution was poured into a polytetrafluoroethylene mold (17 mm x 40 mm x 1 mm) and left to allow the solvent to evaporate at room temperature. The remaining mixture was then heated at 150 °C for 2 hours to produce the polyESO/PCL (50/50 wt%).
Li, Jun, et al. Industrial Crops and Products 185 (2022): 115112.
Pyrrolidone-based ionic liquids are used as catalysts for the ring-opening of epoxidized soybean oil (ESO) to synthesize biopolyols.
Experimental Procedure: 30 g of ESO was weighed and placed in a 250 mL round-bottom flask, and 38 mL of acetone was added. The mixture was stirred (10 rpm) and preheated for 5 minutes at a specified reaction temperature (30-50 °C). Then, a specified amount of water (the molar ratio of water to epoxide groups was 3:1 to 15:1, mol/mol) and a specified amount of ionic liquid (3-7% based on the weight of ESO) were added. The reaction was maintained at the specified reaction temperature (30-50 °C) for 2-6 hours. After the reaction, 3 times the volume of ethyl acetate was added to the flask to dissolve the organic phase, which was then transferred to a 1000 mL separatory funnel. The solution was washed to remove the ionic liquid, repeating the washing 4-9 times with approximately 600 mL of saturated salt solution each time until the aqueous phase became neutral. The organic phase was transferred to a centrifuge tube, and anhydrous sodium sulfate was added to remove trace amounts of water. The mixture was centrifuged to remove the sodium sulfate from the organic phase. Finally, the ethyl acetate in the organic phase was removed under reduced pressure at 50 °C to obtain the DSO (dihydroxy soybean oil).
Xu, Tianle, et al. ACS Omega (2024).
Epoxidized soybean oil, diethylene glycol, and maleic anhydride were used as raw materials to modify cedar wood, aiming to improve its mechanical properties, thermal stability, and water resistance.
Synthesis of Castor Oil-based Unsaturated Polyester: Epoxidized soybean oil and diethylene glycol were mixed in a molar ratio of 1:1.5, and 0.9 wt% of p-toluenesulfonic acid was added. The mixture was placed in a three-neck flask, stirred, and heated to 140 °C. After maintaining the temperature for 4 hours, the epoxy value of the product was determined according to GB/T 1677-1981. Once the epoxy value reached zero, the mixture was cooled to 70 °C, and maleic anhydride, in an amount equal to the moles of hydroxyl groups in the system, was added. The mixture was stirred for 30 minutes to ensure complete mixing, then 1 wt% of N,N-dimethylbenzylamine and 0.02 wt% of hydroquinone were added. The temperature was increased to 90 °C. After 4 hours of reaction, the product EDM, a reddish-brown substance, was obtained.
Wood Sample Modification: First, the wood samples were vacuum-dehydrated for 2 hours at 103±2 °C. They were then placed in a container designed specifically for impregnation. Before introducing the EDM impregnation solution, the samples were subjected to a 2-hour pre-vacuum process (-0.08 MPa). Following this, the samples were immersed at normal pressure for 2 hours to ensure thorough penetration. Finally, the wood chips were heat-treated at 100 °C for 2 hours to complete the modification process.
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