Incorporation of carbon dioxide into soybean oil and subsequent preparation and studies of nonisocyanate polyurethane networks

Abstract

Epoxidized soybean oil was effectively converted to carbonated soybean oil (CSBO) containing fivemembered cyclic carbonates by reaction with carbon dioxide in the presence of tetrabutylammonium bromide as catalyst at 110°C in high yield. CSBO could easily react with di-or tri-primary amines to give the corresponding nonisocyanate polyurethane networks (NIPUs). A model reaction between CSBO and n-butylamine showed the effective ring opening of five-membered cyclic carbonate moieties in the triglyceride molecules by the amine to form ␤-hydroxyurethane systems. NIPUs were further characterized by the three techniques of solvent extraction, dynamical mechanical analysis, and limited tensile testing. The data from these methods confirmed the network character of all materials and also showed how the levels of extractables, Tg, and mechanical properties varied with type of amine and, in the case of ethylenediamine, the effect of stoichiometry. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 92: [883][884][885][886][887][888][889][890][891] 2004

Cyclic Carbonates Based on Vegetable Oils

“…The main part of researches is devoted to epoxidized soybean oil (ESBO) carbonation [6][7][8][9][10][11][12], in some works the epoxidized linseed oil (ELSO) [5,13] is used. Such choice is defined by the availability of these oils which are large-capacity products [14], they are widely applied at halogenated polymers processing (for example, polyvinylchloride).…”

“…Despite the wide range of catalysts, applied to obtain CC [1,2,4], catalytic systems on the basis of tetrabutylammonium bromide (TBAB) have become widely applied for CCVO synthesis [5][6][7][9][10][11][12][13]15], they are a large-capacity industrial product. The optimum of TBAB dosage is 2÷7 mol %, as relating to epoxy groups of a substrate.…”

“…Besides individual TBAB, two-component systems with its application are also described: {ТTBAB + SnCl 4 } [10] and {TBAB + H 2 O} [9]. At the same time such catalytic systems as: sodium iodide, lithium bromide and potassium, benzyltrimethylammonium bromide, ion exchange resins Amberlite IRA-400 (Cl) are [6] of little effect [11], due to their low or full insolubility in the substratum.…”

“…The first work on the receiving of CCVO was carried out at the atmospheric pressure [6] in 2004. In the following years the carbonation of epoxidized oils at the atmospheric pressure was carried out by a number of researchers [5][6][7][8][9]13], who noted a considerable period of time (as a rule, some days) necessary for the achievement of high values of EG oil conversion, and the fast growth of viscosity in the process of carbonation.…”

Seed Oil Based Polyurethanes: An Insight

“…Today, several environment friendly routes for the production of PU have cropped up. Research has been focussed on the preparation of PU from non-isocyanate routes, and also on the use of fatty acid based isocyanates for PU production, considering the persisting challenges of polymer industry and immediate attention sought towards environmentally benign chemicals and chemical routes for the same [9][10][11][12][13][14][15][16][17][18].…”