Synthesis and polymerization of the acrylamide derivatives of fatty compounds

The Ritter reaction of plant oil triglycerides (such as soybean and sunflower oil) with acrylonitrile was used to introduce acrylamide functionality on the triglyceride. Acrylonitrile and triglycerides were reacted in the presence of H2SO4, and acrylamide derivatives were obtained in yields of 45 and 50% for sunflower oil and soybean oil, respectively. Radical initiated copolymerization of the acrylamide derivatives of the triglycerides with styrene produced semirigid polymers. Characterization of new monomers and polymers was done by 1H-NMR, 13C-NMR, IR, and MS. The swelling behavior of the crosslinked network polymers was determined in different solvents. Glass transiton temperature (Tg) of the cured resin was also determined by differential scanning calorimeter to be 40 (degree) C for soybean based polymer and 30 (degree) C for sunflower-based polymer. Homo- and copolymerization behavior of acrylamide derivatives of methyl oleate (MOA) and methyl 10undecenoate (MUA) were also investigated. The reactivity ratios of these monomers with respect to styrene were determined by the Fineman-Ross method using 1H-NMR spectroscopic data. The reactivity ratios were rsty = 1.776; rmoa = 0512 for MOA, and rsty = 1.142; rmua = 0.507 for MUA, respectively. Photopolymerization behaviors of MOA and MUA were also investigated using the photoDSC technique and the rate of polymerization of MUA is higher than that of MOA under the same conditions.