Investigation of the surface properties of polymeric soaps obtained by ring‐opening polymerization of epoxidized soybean oil

Abstract

Epoxidized soybean oil (ESO) was converted to a polysoap (PESO) via a two-step synthetic procedure of catalytic ring-opening polymerization, followed by hydrolysis (HPESO) with a base. Various molecular weights of PESO and HPESO were prepared by varying the reaction temperature and/or catalyst concentration. In addition, the counter ion chemistry was varied by changing the base used for saponification. The PESO and HPESO products were carefully characterized and identified using a combination of FTIR, 1 H-NMR, solid state 13 C-NMR, and GPC. The effect of HPESO polysoaps on the surface tension of water and the interfacial tension of water-hexadecane was investigated as a function of HPESO concentration, molecular weight, and counter ion chemistry. HPESO polysoaps were effective at lowering the surface tension of water and the interfacial tension of water-hexadecane and displayed minimum values in the range of 20-24 and 12-17 dyn/cm, respectively, at concentration of 200-250 lM. Water-hexadecane interfacial tension was also calculated from measured surface tension data using the Antonoff, harmonic mean (HM), and geometric mean (GM) methods. Measured values agreed well with those calculated using the HM and GM methods, but not the Antonoff method.

Green Nanocomposites from Renewable Plant Oils and Polyhedral Oligomeric Silsesquioxanes

“…Epoxidized plant oils are commercially available as stabilizers for the processing of poly(vinyl chloride) and modifiers for coatings [33,34]. Acrylates and polyols derived from epoxidized plant oils have also been used as a monomer for preparation of bio-based polymeric materials.…”

Synthesis and characterization of castor oil-based polymeric surfactants

“…Stock solutions of 0.2% aqueous HPECO-M were prepared according to the following procedure [25] : 0.5 g of HPECO was weighed into a 50 mL beaker and the required amount of NaOH or KOH solution (to neutralize all carboxylic acid groups) was added into the beaker. Then, the resulting solution was transferred to a 250 mL volumetric flask.…”

Soybean-based Surfactants and Their Applications

“…The resulting polymer was hydrolysed with a base to remove the glycerin backbone from the oil structure and obtain a polymer with free carboxylic acid groups. The resulting polyacid was then converted into polysoap by neutralising it with an appropriate base (NaOH) [Biresaw et al, 2008;Liu & Erhan, 2010]. Recently, efforts have been paid to the preparation of ESO-derived surfactants using the environmentally-friendly solvent SC-CO 2 , targeting applications in food, pharmaceutical delivery, and cosmetics.…”

“…The surface tension of Milli-Q water was reduced to a minimum value of less than 30 mN/m. The surface activity was found to be affected by the type of counter ion and molecular weight [Biresaw et al, 2008]. An ESO-derived surfactant, Palozengs (R-004), exhibited a unique aggregation behaviour and formed small aggregates (sub-micelles or pre-micelles) at very low concentrations.…”