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Polyols from vegetable oils can replace petroleumbased polyols in the preparation of polyurethanes and polyesters in a wide range of applications. However, previous preparation methods are either too costly, inefficient, or yield secondary alcohols, which are less reactive than the desired primary alcohols. The objectives of this study were to prepare primary soy-based polyols by a new catalytic ozonolysis process and to characterize the composition of the product mixture. In this new process, the polyols were prepared by passing ozone through a solution of soybean oil and ethylene glycol in the presence of an alkaline catalyst. Unlike conventional ozonolysis that yields aldehydes and carboxylic acids by spontaneous decomposition of the ozonide intermediates, the ozonides in our method reacted with the hydroxyl group of the glycol to form an ester linkage with a terminal hydroxy group. Statistical analysis of the product mixture indicates that the resulting polyol mixture is more uniform than the original TG mixture, having (2-hydroxy)nonanoate as the major component of the new hydroxyl functional TG. The chemical structure of the polyols produced was further characterized by iodine number and 13 C NMR and FTIR spectroscopy, which confirmed the cleavage of the double bonds, the presence of hydroxyl groups, and the formation of new ester linkages.Paper no. J10972 in JAOCS 82, 653-659 (September 2005). FIG. 3.Statistical distribution of soy polyols obtained by alkaline catalytic ozonolysis of soybean oil with ethylene glycol. N, nonanoate; P, palmitate; S, stearate.

Blends of soy protein concentrate and biodegradable polyester (Eastar Bio Copolyester, EPE) were prepared by using glycerol as a compatibilizing agent. Good miscibility was obtained only when the soy protein was initially combined with glycerol under high shear and at elevated temperatures in an extruder. Under these conditions, partial denaturing of the soy protein led to specific interactions between functional groups of the protein with the glycerol. The extrusion conditions and appropriate screw configuration were the critical factors affecting the reactivity of the protein and hence, the properties of the blends. Screws with large kneading blocks that produced high shear mixing were preferred and led to thermoplastic blends characterized by high elongation and high tensile strength. The morphology of these soy protein/polyester blends was studied by using environmental scanning electron microscopy (ESEM) and indicated good wetting of the soy protein particles within the polyester matrix. The thermal properties were studied by differential scanning calorimetry (DSC) and showed a lower degree of crystallinity and a continuous depression of the melting point of the polyester as the concentration of protein was increased. The possibility of using soy protein concentrate instead of the more expensive (higher purity) soy protein isolate in the preparation of biodegradable resins should lead to new commercial opportunities based on renewable, agricultural byproducts.

ABSTRACT:Composites with good mechanical properties were prepared from chemically modified soy oils and biofibers without additional petroleum-based polymers. These composites were prepared from maleic anhydride and epoxide functionalized soybean oils that were cured in the presence of various biofibers (e.g., kenaf, kayocell, protein grits, and solka-floc) by a flexible amine catalyst. Rigid thermosets characterized by a high-crosslink-density network and a high gel fraction were obtained. Fourier transform infrared was used to follow the cure reaction via the disappearance of the characteristic anhydride adsorptions. Composites with high tensile strength and low elongation were obtained when kenaf fibers were treated with (2-aminoethyl)-3-aminopropyl-trimethoxysilane and then added to the epoxidized/maleated soy matrix and cured with hexamethylenediamine. These biobased composites could provide inexpensive epoxy resin alternatives for a wide variety of industrial applications.