Butanethiol was used in ultraviolet-initiated thiol-ene reaction with canola and corn oils to produce sulfide-modified vegetable oils (SMVO). The crude SMVO product was successfully purified by solvent extraction, vacuum evaporation, and silica gel chromatography. The SMVO products were characterized by nuclear magnetic resonance and Fourier transform infrared spectroscopy. Further product characterization and analysis was conducted using GC and GC-MS on the fatty acid methyl esters obtained by the transesterification of the SMVO products. Investigation of the effect of reaction conditions showed that high yield and high conversion of double bonds into thiol were favored at low reaction temperatures and high butanethiol/vegetable oil ratios. Canola and corn oils gave similar double-bond conversions and yields of the desired SMVO product even though they have big differences in the relative numbers of single and multiple double bonds in their structures. Under best reaction conditions, up to 97% of double-bond conversion and 61% isolated yields of the purified SMVO products were attained.

Biopolymers are preferred ingredients for the manufacture of materials because they are based on abundantly available and renewable raw materials that have benign environmental problems associated with their production, fabrication, use, and disposal; however, the wide use of biopolymers in engineering applications has not been achieved, mainly because of the inferior quality of many biopolymer‐based products. To overcome this limitation, studies have been initiated on blends of biopolymers and biodegradable synthetic polymers. We used the contact angle of probe liquids to measure the surface energy of polystyrene, the biodegradable polyesters polycaprolactone, poly(hydroxybutyrate‐co‐hydroxyvalerate), polylactic acid, polybutylene adipate terephthalate, and adipic poly(hydroxy ester ether), and normal starch. The surface energies were used to estimate the starch/polymer interfacial energy and work of adhesion. The calculated starch/polyester work of adhesion showed mixed correlation with published starch/polyester mechanical properties, indicating that factors other than interfacial properties might be dominant in determining the mechanical properties of some starch/polyester blends. © 2001 John Wiley & Sons, Inc. J Polym Sci B: Polym Phys 39: 920–930, 2001

The steel/steel boundary friction properties of soybean oil (SBO) and high-oleic soybean oil (HOSBO) are compared. HOSBO is significantly more saturated than SBO and more oxidatively stable. Changes in degree of unsaturation affect lateral interactions of adsorbate molecules, which in turn affects their adsorption and, hence, their boundary lubrication properties. To investigate this possibility, the free energies of adsorption (∆G ads ) of SBO, HOSBO, and methyl laurate (ML) were determined from the analysis of friction-derived adsorption isotherms using the Langmuir and Temkin adsorption models. The results showed a stronger adsorption for the vegetable oils than for ML, an indication of multiple interactions between the ester groups of the triglycerides and the steel surface. The result also showed no difference in the ∆G ads values of SBO and HOSBO obtained using either the Langmuir or Temkin models. This was interpreted as an indication of the lack of appreciable net lateral interaction between triglyceride adsorbates.