Polymerized soybean oils of different molecular weights were used as plasticizers in NR/SBR compositions. The oils of different molecular weights and viscosities were synthesized by cationic polymerization using a proprietary technology. Because vegetable oils have double bonds, they are not only viscosity depressants but also active participants in cross-linking reactions. Properties of elastomers extended with different concentrations of mineral oil or pure soybean oil were compared with elastomers extended by polymerized oils of different molecular weights at the same concentrations. It was found that polymerized soybean oil could be substituted for naphthenic process oil with minimal differences in mechanical and dynamic properties.
Novel high hydroxyl number and high functionality polyols were developed using thiol-ene reaction of castor oil with mercaptoethanol or mercaptanized castor oil with allyl alcohol (by photochemical reaction) and 2-hydroxyethyl acrylate (by Michael thiol-ene reaction). The polyols had OH numbers of 220-295 mg KOH/g and functionalities close to 6. Cast polyurethane resins were prepared with methylene diphenyl diisocyanate (MDI), dicyclohexylmethane-4,4'diisocyanate (HMDI) and m-xylylene diisocyanate (XDI). XDI gave rubbery to leathery polyurethanes with all three polyols, while MDI and HMDI gave amorphous glasses with good mechanical properties. Rigid polyurethane foams of good properties were made with MDI and three castor oil-based polyols.
A new class of biopolymers based on plant oils with allylic double bonds was prepared from vegetable oils by oxirane ring-opening. Investigation of model systems revealed that the main side reactions during ring-opening were formation of intramolecular cyclic ethers in epoxidized linoleic fatty ester and oligomerization. Side reactions in the epoxidized oleic fatty ester were insignificant. Allyl alcohol ring-opened epoxidized soybean oil (AESBO) was then copolymerized with maleic anhydride (MA) to prepare thermosetting resins by free radical polymerization and esterification. In the best case, high gel content (99%), low water absorption (∼1%), and low swelling ration in toluene (∼4%) were achieved. Glass transition temperatures of these resins ranged from below room temperature to about 123 °C depending on the loading of MA. Tensile modulus varied from few MPa to 1.1 GPa, with the highest tensile strength of 29 MPa.
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