The polymerization products of epoxidized oleic acid and epoxidized methyl oleate with cis-1,2-cyclohexanedicarboxylic anhydride and triethylamine as the initiator: Chemical structures, thermal and electrical properties

Oligo and polyesters were prepared from epoxidized oleic acid (EOA) and methyl oleate (EMO) in polymerization reaction with cis-1,2-cyclohexanedicarboxylic anhydride (CH) and triethylamine (TEA) as the initiator at 165 °C for 3 h. In order to increase the molecular weight of the products, a small amount of butanodiol diglycidil ether (BDGE) was added. The different steps of the reactions were elucidated by nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopy (FTIR) and differential scanning calorimetry (DSC). These same techniques as well as size exclusion chromatography (SEC), thermogravimetric analysis (TGA) and electric impedance spectroscopy (EIS) were used to characterize the products of the EMO/CH/TEA, EMO/CH/BDGE/TEA, EOA/CH/TEA and EOA/CH/BDGE/TEA reaction systems. The formation of internal ester groups was confirmed by NMR and FTIR. The Mw products are between 2500 g/mol and 85000 g/mol. The ΔΗ values are 44.6 KJ/ee and 42.7 KJ/ee for the EOA and EMO systems, respectively. The thermal degradations of the products start at temperatures higher than 180 °C. All of the products reveal glass transitions between − 57 °C and − 14 °C, while the EMO ones also present crystallization-like behavior at − 7 °C and 3 °C. The dielectric properties of the products include very high resistivity and low capacitance.