Polymerization Of Epoxidized Soybean Oil Research Articles

Interfacial compatibilization via in-situ polymerization of epoxidized soybean oil for bamboo fibers reinforced poly(lactic acid) biocomposites

A simple, efficient and eco-friendly method was developed for improving the interfacial adhesion of bamboo fibers (BFs) reinforced poly(lactic acid) (PLA) biocomposites. A biobased monomer, i.e., epoxidized soybean oil (ESO), was used to in-situ polymerize at the interface between BFs and PLA matrix for forming a polymerized ESO interfacial layer. FTIR and XPS analyses confirmed that the poly(ESO) layer was covalently bonded with both BFs and PLA matrix, resulting in an enhanced interfacial adhesion of the BF/PLA biocomposites. The flexible poly(ESO) layer contributed to a simultaneous strengthening and toughening effect on the biocomposites, hence significantly increased the tensile strength, tensile modulus, fracture elongation, and storage modulus of the biocomposites. However, the glass transition temperatures, melting temperatures, and cooling crystallization temperatures of the biocomposites were slightly decreased due to the incorporation of ESO.

Manufacturing of Thermally Remoldable Blends from Epoxidized Soybean Oil and Poly(lactic acid) via Dynamic Cross-Linking in a Twin-Screw Extruder

Fully biobased, thermally remoldable, and highly tough blends were formulated from epoxidized soybean oil (ESO) and poly(lactic acid) (PLA) in a large-scale production via twin-screw extrusion and injection molding. During the melt-compounding of PLA and ESO, self-polymerization of ESO occurred in the presence of cationic initiator to form a polymerized ESO (PESO) rubbery phase within PLA matrix. The weight ratios of ESO to PLA ranging from 1:9 to 4:6 were designed to tailor the properties of the formed PESO/PLA blends such as crystallization behavior, rheological properties, mechanical properties, thermal stabilities, and morphologies. The PESO/PLA blends exhibited significantly increased elongation at break, tensile toughness, crystallinity, and complex viscosity when compared to pure PLA due to the formation of a two-phase separated structure in the blends; however, significant decreases in tensile strength, tensile modulus, storage modulus, and glass transition temperature of the blends were observed ...

Catalyzed ring-opening polymerization of epoxidized soybean oil by hydrated and anhydrous fluoroantimonic acids

Ring-opening polymerization of epoxidized soybean oil (ESO) catalyzed by a superacid, fluoroantimonic acid hexahydrate (HSbF6·6H2O) and the anhydrous form (HSbF6) in ethyl acetate was conducted in an effort to develop useful biodegradable polymers. The resulting polymerized ESO (SA-RPESO and SAA-RPESO) was characterized using infrared spectroscopy, differential scanning calorimetry, thermogravimetric analysis (TGA), 1H-NMR, 13C-NMR, solid-state 13C-NMR and gel permeation chromatography (GPC). The results indicated that ESO was effectively polymerized by fluoroantimonic acid and formed polymers with relatively high cross-link density. Glass transition temperatures of these polymers ranged from –13°C to –21°C. TGA results showed the SA-RPESO and SAA-RPESO polymers were thermally stable at temperatures up to 200°C. Decomposition of the polymers was found to occur at temperatures greater than 350°C. GPC results indicated the extracted soluble substances from SA-RPESO polymers were oligomers of ESO. These soybean oil–based polymers will be explored for application in the personal and health care areas.

Fluoroantimonic acid hexahydrate (HSbF6·6H2O) catalysis: The ring-opening polymerization of epoxidized soybean oil

Ring-opening polymerization of epoxidized soybean oil (ESO) catalyzed by a super acid, fluoroantimonic acid hexahydrate (HSbF6·6H2O) in ethyl acetate was conducted in an effort to develop useful biodegradable polymers. The resulting polymerized ESO (SA-RPESO) was characterized using infrared (IR) spectroscopy, differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), 1H NMR, 13C NMR, solid state 13C NMR, and gel permeation chromatography (GPC). The results indicated that ESO was effectively polymerized by fluoroantimonic acid and formed polymers with relatively high crosslink density. Glass transition temperatures of these polymers ranged from −13°C to −21°C. TGA results showed the SA-RPESO polymers were thermally stable at temperatures up to 200°C. Decomposition of the polymers was found to occur at temperatures greater than 350°C. GPC results indicated the extracted soluble substances from SA-RPESO polymers were oligomers of ESO. These soybean oil-based polymers will be functionalized to hydrogels and their applications explored in the personal and health care areas.

Ring‐Opening Polymerization of Epoxidized Soybean Oil

AbstractRing‐opening polymerization of epoxidized soybean oil (ESO) catalyzed by boron trifluoride diethyl etherate (BF3·OEt2) in methylene chloride was conducted in an effort to develop useful biodegradable polymers. The resulting polymerized ESO (PESO) were characterized using infrared (IR) spectroscopy, differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), 1H NMR, 13C NMR, solid state 13C NMR and gel permeation chromatography (GPC). The results indicated that PESO materials were highly crosslinked polymers. They had glass transition temperatures ranging from −16 to −48 °C. TGA results showed the PESO polymers were thermally stable at temperatures up to 220 °C. Decomposition of the polymers was found to occur at temperature greater than 340 °C. GPC results indicated the extracted soluble substances from PESO polymers were ESO dimers, trimers and polymers with low molecular weights. The resulting crosslinked polymers can be converted into hydrogels by chemical modification, such as hydrolysis. These soy based hydrogels will find applications in personal care and health care areas.

Viscoelastic Properties of a Biological Hydrogel Produced from Soybean Oil

AbstractHydrogels formed from biopolymers or natural sources have special advantages because they may have biodegradable and biocompatible properties. The viscoelastic properties of a newly developed biological hydrogel made from epoxidized soybean oil (ESO) were investigated. The material called HPESO is a hydrolytic product of polymerized ESO (PESO). HPESO exhibited viscoelastic solid or gel behavior above 2% (wt. %) concentration at room temperature and viscous liquid behavior at 55 °C. The thermal assembly disassembly reassembly function of the HPESO hydrogel was completely reversible. The viscoelastic properties of HPESO were dependent on concentration. Analysis of modulus and concentration dependence and stress relaxation measurement indicated that HPESO was a physical gel where the cross‐linkers between the molecules were physical junctions. HPESO hydrogel also exhibited fast initial recovery of its viscoelastic properties after being subjected to mechanical shear disruption. The function and behavior of the HPESO hydrogel suggest that this biomaterial may be suitable for applications in drug delivery and scaffolds of bioengineering and tissue engineering.

Biodegradation Behavior of Some Vegetable Oil-Based Polymers

The potential biodegradability of several vegetable oil-based polymers was assessed by respirometry in soil for 60-100 days at temperatures of 30-58°C. Films of soybean oil and linseed oil which were oxidatively polymerized (Co catalyst) on a kraft paper support were 90%-100% mineralized to CO2 after 70 days at 30°C. Mineralization of polymerized tung oil to CO2 was much slower than soy or linseed oils. Mineralization of epoxy resins made from epoxidized soybean oil (ESO) and aliphatic dicarboxylic acids was rapid while mineralization of similar resins made with a triacid (citric) was slower. There was no significant degradation of polyamine/ESO resins after 100 days at 58°C. Mineralization of the available carbon in vegetable oil polyurethanes and cationically polymerized ESO was less than 7.5% after 70 days at 30°C and 25 days at 55°C compared to 100% for soybean oil. From these results, it appears that triglycerides highly cross-linked with non-degradable linkages are not biodegradable to a significant extent while triglycerides cross-linked with hydrolysable bonds such as esters remain biodegradable.