Synthesis and characterization of triglyceride-based polyols and tack-free coatings via the air oxidation of soy oil

The effect of time and temperature on the air oxidation of soybean oil in the absence of catalysts or added initiators was investigated. It was possible to divide the air oxidation of soybean oil into three regimes. The first regime of air oxidation resulted in insignificant change in the hydroxyl number. During this regime, it was proposed that natural antioxidants, which are present in raw soybean oil, were consumed and peroxide formation occurred. A drastic increase in hydroxyl number due to the formation and subsequent decomposition of peroxides marked the second regime of air oxidation. In the third regime of air oxidation, free radical crosslinking of the soybean oil occurred, and an insoluble gel was formed. The three regimes of air oxidation were used as a guide for the preparation of soy-based polyols and crosslinked polymers. Crosslinked, tack-free coatings were prepared from a metal catalyzed oxidation of soybean oil, where soybean oil and ambient oxygen were the only reactants. Higher temperatures (125°C) were more efficient than lower (50°C) for obtaining high gel fractions and tack-free coatings. Cure of the coatings was expedited with exposure of the coating to UV irradiation after initial heating. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 102: 690–697, 2006