Synthesis and characterization of castor oil-based polymeric surfactants

Dehydrated castor oil was epoxidized using phosphoric acid as a catalyst and acetic acid peroxide as an oxidant to produce epoxidized castor oil (ECO). Ring-opening polymerization with stannic chloride was used to produce polymerized ECO (PECO), and sodium hydroxide used to give hydrolyzed PECO (HPECO). The HPECO was characterized by Fourier transform infrared, ¹H and ¹³C nuclear magnetic resonance spectroscopies, gel permeation chromatography, and differential scanning calorimetry. The weight-average molecular weight of soluble PECO and HPECO were 5026 and 2274 g·mol^-1, respectively. PECO and HPECO exhibited glass transition. Through neutralizing the carboxylic acid of HPECO with different counterions, castor oil-based polymeric surfactants (HPECO-M, where M= Na⁺, K⁺ or triethanolamine ion) exhibited high efficiency to reduce the surface tension of water. The critical micelle concentration (CMC) values of HPECO-M ranged from 0.042 to 0.098 g·L^-1 and the minimum equilibrium surface tensions at CMC (g_cmc) of HPECO-M ranged from 25.6 to 30.0 mN·m^-1. The water-hexadecane interfacial energy was calculated from measured surface tension using harmonic and geometric mean methods. Measured values of water-hexadecane interfacial tension agreed well with those calculated using the harmonic and geometric mean methods.