Characterization and Polymerization of Epoxidized Methacrylated Castor Oil

Abstract

In this study, synthesis and polymerization of epoxidized methacrylated castor oil (EMETCO) is demonstrated. EMETCO is synthesized in two steps. Castor oil (CO) is methacrylated with methacryloyl chloride at the first step. Then the methacrylated castor oil (METCO) is epoxidized by Prilezhaev reaction. Structure of EMETCO is determined by 1H NMR and IR techniques. EMETCO was copolymerized with acrylic acid (AA), styrene (ST), and methacrylic acid (MA). Thermal and mechanical properties of the synthesized polymers are evaluated. Among the polymers synthesized EMETCO‐ST‐MA polymer gives the highest storage modulus at 2.25 GPa. On the other hand, EMETCO‐AA copolymer exhibited the lowest storage modulus at 350 MPa. Moreover, EMETCO‐ST copolymer shows the lowest 5% weight loss temperature while EMETCO‐MA exhibited the highest 5% weight loss temperature at 280 °C. Practical Applications: Epoxidized Methacrylated Castor Oil is a bio‐based epoxy acrylate monomer. The low viscosity and two different functional groups make this material suitable for many polymerization reactions and applications. This compound would be used as a replacement materials for many industrial monomers such as styrene, acrylated epoxidized soybean oil, or prepolymers in the future. EMETCO is a castor oil based epoxy acrylate monomer. It is a hybrid material that contains different types of polymerizable groups. Synthesis of the monomer is not complicated and completed in two steps. Methacrylation of castor oil occurs at the first step and epoxidation follows that reaction. The resultant compounds is a transparent oil.

Bio‐Based Polymers Obtained from Modified Fatty Acids and Soybean Oil with Tailorable Physical and Mechanical Performance

“…As expected, all the reactants present the characteristic absorption bands for ─CH 2 and ─CH 3 asymmetrical and symmetrical stretching vibrations, in the 2800–3000 cm −1 region. The signal corresponding to the ester carbonyl, [ 20 ] appearing at 1725 cm −1 for MLA and MOA precursors, as well as that of OH groups that appears at 3500 cm −1 , confirm the successful chemical modification of the fatty acids, which originally have carboxylic acid groups (1705 cm −1 ) but not ─OH or ester groups. Most important is the appearance of signals at 810, 940, 1637, and 1160 cm −1 in the MLA and MOA spectra that were absent in the raw fatty acids.…”

“…These signals can be ascribed to the out‐of‐plane bending, twisting, and wagging and stretching of C═C bonds, and to the stretching vibrations of the C─O─C bonds, [ 9 ] respectively, which were formed due to the chemical addition to GMA. Moreover, it can be noticed that a small peak at 3002 cm −1 is also present in the spectra of the MOA, since it corresponds to the absorption of aliphatic C═C bonds [ 20 ] of oleic acid chains, indicating that the unsaturations of the fatty acid originally present were preserved during the chemical reaction. In addition, the small signal at 910 cm −1 , attributed to the epoxy groups (γC─O) is barely visible in the spectra of MOA and MLA, accounting for the 10% excess of GMA used in the precursors’ synthesis.…”

Development of castor oil–based polymers: A review

“…When cured with poly(amidoamine), the polymer had high elongation, tensile strength, toughness, flexibility, and impact resistance that surpass that of commercial epoxy thermosets. Çayli et al synthesized epoxidized methacrylated (EMETCO) castor oil and was copolymerized with three monomers: acrylic acid (AA), styrene, and methacrylic acid. Among the polymers synthesized, EMETCO‐ST‐MA polymer gave the highest storage of modulus at 2.25 GPa.…”

Opportunities for the Use of Brazilian Biomass to Produce Renewable Chemicals and Materials

“…CBO can easily react with isocyanates, carboxylic acids and anhydrides, due to its high ricinoleic acid (and thus OH group) content [190,191] . As a result, CBO polyurethane foams doped with titanium particles were found to be promising materials for bone repair [190] .…”

“…[189] CBO can easily react with isocyanates, carboxylic acids and anhydrides, due to its high ricinoleic acid (and thus OH group) content. [190,191] As a result, CBO polyurethane foams doped with titanium particles were found to be promising materials for bone repair. [190] Furthermore, polyurethane coatings showed a good ability to release nitrogen-based compounds over long time periods (about 70 days).…”