Syntheses and properties of cross-linked polymers from functionalized triglycerides

A number of functionalized triglycerides were synthesized from glyceryl trioleoate via epoxidation followed by reduction to give glyceryl tris(9-hydroxy)trioleoate (a triol) or hydrolytic ring opening to obtain glyceryl tris(9,10-dihydroxy)trioleoate (a hexaol). A selective monoepoxidation reaction of glyceryl trioleoate was also carried out and the resulting monoepoxide was hydrolyzed to give glyceryl 9,10-dihydroxytrioleoate (a diol). Glyceryl tris(9-hydroxy)trioleoate was brominated followed by displacement with sodium azide and reduction to give glyceryl tris(9-amino)trioleoate (a triamine) and glyceryl tris[9-(N-isopropylamino)]trioleoate. These functionalized triglycerides were crosslinked with 1,4-phenylene diisocyanate. The crosslinked polymers exhibit thermost characteristics. Thermal analysis results suggest that the polymers are in amorphous states, and their thermal stability was significantly affected by crosslink degree. The crosslinked polymer derived from the diol retained 56% of its weight at 408 C, whereas the polymers derived from the aforementioned hexaol with higher crosslink degree retained only 36% of the original weight. Glass transition temperatures of these polymers range from -1.0 degrees C to 10.2 degrees C. The thermal stable polymer, 12, derived from the aforementioned diol exhibits a linear viscoelastic character and can be used as thermoplastics. (C) 2008 Wiley Periodicals, Inc.