BIOBASED SEGMENTED POLYURETHANES FROM METHYL OLEATE BASED POLYETHER POLYOLS

In the polyurethane industry, conventional polyether polyols are mostly produced from petroleum-based alkylene oxides. Due to uncertainty about the future cost of petroleum, as well as the desire to move toward more environmentally friendly feedstocks, many recent efforts have focused on replacing all or part of the conventional petroleum-based polyols with those made from renewable resources such as vegetable oils. In addition, it is a challenge to use diisocyanates derived from aminoacids, making possible to produce polyurethanes completely from renewable resources.1-3

In this work we report the synthesis and characterization of polyether polyols from methyl oleate. The coordinative ring opening polymerisation of epoxidized methyl oleate yields a linear polyether with Mn= 6.500 Da. The controlled reduction of the carboxylate groups allows to obtain a set of polyether polyols with different primary hydroxyl contents. Depending on the degree of reduction the polyols can have different properties and, when converted to polyurethanes, may impart different properties to the final product.

These renewable polyols react with 4,4’-methylenebis(phenyl isocyanate) (MDI) or L-lysine diisocyante (LDI) to yield polyurethanes with different crosslinking density. Moreover, we carried out the reaction of the polyetherpolyol with the isocyanates and 1,3-propanediol as chain extender to obtain segmented polyurethanes with different hard segment contains. These materials were characterized by infrared spectroscopy (FTIR/ATR), differential scanning calorimetry (DSC), termogravimetric analysis (TGA) thermodynamomechanical analysis (DMTA), scanning electron microscope (SEM) and X-Ray difraction.

1 M.A.R. Meier, J.O. Metzger and U.S. Schubert, Chem. Soc. Rev., 2007, 36, 1788–1802
2 F. S. Günera, Y.Yagci, A.T. Erciyes, Prog. Polym. Sci. 31 (2006) 633–670
3 G. Lligadas, J.C. Ronda, M. Galià, V. Cádiz, Biomacromolecules, 2007, 8, 686-692