Polymerization of plant oils with p-dinitrosobenzene

Abstract

In this study, tacky, black coloured thermoset polymers were synthesized from polymerization of the soybean oil (SO) with polymeric p-dinitrosobenzene (PDNB) via an ene reaction. The crosslinking agent, polymeric dinitrosobenzene was synthesized using pquinone dioxime and characterized by IR spectroscopy. Two different methods were used for the polymerization: solventless and solvent mediated. In the first method SO/PDNB polymers were synthesized by a two stage polymerization. During the reaction different parameters such as mole ratio of SO and PDNB, pre-heating temperature of SO, polymerization time and temperature were examined. The crosslinking reactions were followed by IR spectroscopy, and the polymers obtained were characterized by dynamic mechanical analyzer, thermo gravimetric analyzer and differential scanning calorimetry. The crosslinked network structure of the polymers was investigated by swelling behavior and surface hardness test. The second method of polymerization used an emulsion polymerization in which hot water was used as continuous phase. However as the water acted as inhibitor the polymers obtained were not suitable for mechanical analysis, only the examination of the polymerization by IR spectroscopy was feasible. Methyl oleate was used as a model compound to examine the details of the chemical structure of the products, however the samples synthesized were highly crosslinked. Thus only IR spectroscopy characterization was possible.