Epoxidized soybean oil was reacted with cinnamic acid with triphenyl phosphine as a catalyst. Cinnamic acid reacted with 79% of the available epoxy groups, and this yielded cinnamate esters of epoxidized soybean oil (ESOCA). 1 H-NMR, IR, and mass spectra of the new cinnamate derivatives confirmed the proposed structure. The mass spectra revealed that the average number of cinnamate groups per triglyceride molecule was 3.33. ESOCA could be photopolymerized with UV light. ESOCA could also be homopolymerized into a soft and insoluble polymer by freeradical initiation and copolymerized with styrene, vinyl acetate, and methyl methacrylate. A mixture of ESOCA with 25 wt % styrene had a viscosity of 410 cP and could be free-radically polymerized with benzoyl tert-butyl peroxide at elevated temperatures. Differential scanning calorimetry confirmed the formation of copolymers. The ESOCA homopolymer and its copolymers all showed a first-order transition by differential scanning calorimetry around Ϫ1.5°C that was attributable to side-chain relaxations of the triglyceride fatty acids. The styrene copolymer of ESOCA showed a tan ␦ peak at 66.6°C.

Epoxidized soybean oil (ESO) was reacted with monomethyl maleate with AMC‐2 catalyst. Monomethyl maleate was found to react with 65% of the available epoxy groups to give the monomethyl maleic esters of ESO (MESO). 1H‐NMR, 13C‐NMR, and IR spectra of the new derivative confirmed the proposed structure. The NMR spectra revealed that the average number of monomethyl maleate groups per triglyceride molecule was 2.6. MESO was photopolymerized with ultraviolet light and was free radically homopolymerized and copolymerized with styrene (STY), vinyl acetate (VA), and methylmethacrylate (MMA). MESO was also reacted with maleic anhydride at the newly formed hydroxyl groups to give maleinized MESO, (MESOMA), which now contained 4.9 maleate unsaturations per triglyceride. Dynamic mechanical analysis revealed the dynamic modulus for styrene copolymers of MESO and maleinized MESO as 105 and 140 MPa, respectively. Both of these plant oil derived monomers are good candidates for a practical and economical liquid molding resin. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 103: 626–633, 2007

In this study, a new type of bifunctional monomer from castor oil was investigated and the properties of the polymers that were obtained from this monomer were also evaluated and compared with the polymers that were obtained from acrylated epoxidized soybean oil (AESO). Castor oil (CO), first, was reacted with acryloyl chloride in order to obtain acrylated castor oil (ACO). Epoxidized acrylated castor oil (EACO) was obtained after the epoxidation reaction. EACO was characterized by 1H NMR and IR techniques. Viscosity of the monomer was also determined. The viscosity of EACO was found as 1950 centipoise by using Brookfield type viscometer at 20°C. After characterization, homo and block copolymers of the EACO with methyl methacrylate (MMA) and acrylic acid (AA) were synthesized by conventional radical polymerization techniques. Transparent and tough polymers were obtained after polymerization reactions. Thermal and mechanical properties of the polymers synthesized were also evaluated. EACO‐AA (85–15%) copolymer showed 0.7 GPa storage modulus while AESO‐AA (85–15%) copolymer showed only 0.37 GPa modulus. When compared 5% weight loss temperatures as a thermal stability indicator, it was observed at 332°C for AECO‐AA copolymer and 295°C for AESO‐AA copolymer. Practical applications: Epoxidation and polymerization of EACO was demonstrated in this manuscript. EACO is a new type of monomer that contains a reactive epoxy and acrylate group. This monomer is a versatile monomer and can be applied in a wide variety of areas. EACO synthesis is completed in two steps. Castor oil is acrylated first at 0°C in the presence of triethyleneamine. The acrylated castor oil is then selectively epoxidized by HCOOH/H2O2 mixture.

No abstract

A combination of simultaneous photoinduced electron transfer and photoinduced CuAAC processes enables the in-situ preparation of antibacterial thermosets containing silver nanoparticles (AgNPs) in one-pot. Upon photolysis of photoinitator, the generated radicals not only reduce Cu(II) into Cu(I) activator to catalyst the CuAAC click reaction, but also simultaneously generate AgNPs from AgNO 3 through electron transfer reaction. Due to their reduction potentials difference, the polymer matrix is formed before the formation of AgNPs, assisting to eliminate the agglomeration of them. The thermoset structures are confirmed by FT-IR and solubility tests, whereas the presence of AgNPs is proven by transmission electron microscopy with energy dispersive X-ray system analyzer. The samples containing 5 and 10% AgNPs exhibited strong inhibition zones, where all kinds of bacteria (gram-positive (Staphylococcus Aureus) and gram-negative (Escherichia Coli)) were killed in the surrounding of the film samples.