Plant oil based polymerizable monomer synthesis and polymerization reaction

Utilization of natural products such as vegetable oils and natural fats has attracted great attention in both scientific and industrial application in recent years due to increasing economic, environment and sustainability concerns. Common vegetable oil are triglirids containing five major fatty acids (C18:1) oleic, linoleic (C18:2) linolenic (C18:3); palmitic (C16:0) and stearic (C18:0). Soybean oil has common %25 oleic, %50 linoleic, %3-9 linolenic and about %15 of palmitic and stearic acids. Lateral double bonding vegetable oils are less reactive to free radical polymerization. Cationic polymerization of vegetable oils in the presence of Lewis acid, such as BF3, has been described in literature. However, only viscous and rubbery polymers were obtained. Polymerization of vegetable oil gave low molecular weight oligomers. All mentioned process did not yield solid products with useful engineering properties. General methods of making solid polymers films from trigliserids involve functionalizing oils to polyols, polyacids or polyamines and then reacting them with isocyanates or other compounds to make polyesters, polyureas or polyurethanes. Such tecniques, although very useful in many applications, may involve multistep syntheses, utilization of toxic and expense reactants such as isocynates and sacrificing useful properties as increasing dielectric constant and dielectric loss compared to the starting oils. Ideal vegetable oil casting resins would allow radical or other types of polymerization directly into polymeric products at low or mild temperatures with high biomass content and without byproduct. These systems may involve terminal or internal double bonds which are easily polymerized by standart polymerization mechanism. At first, allyl alcohol modified epoxidized soybean oil, which containing a double bond, was cured presence of thiol compound by convenient polymerization method then was investigated to obtain more rigid termoset material. New using application will be generated if vegetable oil triglycerides are modified and enriched with functional groups at monomer phase. Since, physical and chemical properties of the polymers can form as desired at the beginning of synthesis step. The synthesized monomers are referred to as epoxy resin. Material which is obtained by resins curing can be used as coating and film. The provided epoxide soybean oil and allyl alcohol is reacted by the ring opening reaction then curing reaction was performed to obtain film material. At the first step, epoxy ring of epoxidized soybean oil was opened with acidic catalyst and allyl alcohol was linked to trigliserid backbone chain. Allyl epoxidized soybean oil contains functional groups such as unsaturated double bond and a hydroxyl group. For carrying out this reaction, different catalysts, reactant ratios, temperatures and reaction times were studied. Epoxy ring opening reactions were followed up with FT-IR analysis and iodine value determination methods. Allyl epoxidized soybean oil was characterized with GPC, 1H-NMR, 13C-NMR and epoxy oxygen determination methods. The reaction was reached at about 50% yield. Due to the reactive unsaturated double bonds on the allyl alcohol, allyl epoxidized soybean oil is suitable for the polymerization reaction. Photo polymerization reactions of liquid the polyene and polythiol compounds which comprising multi-functional groups, has been described in the literature and patents. Allyl epoxidized soybean oil containing about 2 unsaturated double bonds per triglyceride molecule, pentaerythritol tetrakis containing 4 functional thiol groups and UV photo-initiator mixture were prepared then is crosslinked. Molar ratio of unsaturated double bonds to the functional -SH groups 1: 1 is based on, the samples were prepared by varying the ratio of photo-initiator. Mixture of polyene and polythiol compounds are photopolymerized then crosslinked samples were characterized with spectroscopical, thermal and mechanical characterization methods. All mentioned on this thesis is, reaction soy-based compounds to obtain cross-linked coating and the film materials and identify different properties of the materials by characterization methods.