Non-Isocyanate Polyurethane Synthesis by Polycondensation of Alkylene and Arylene Bis(fluoroalkyl) Bis(carbonate)s with Diamines

Abstract

Abstract Alkylene and arylene bis(fluoroalkyl) bis(carbonate)s (BFBCs) were quantitatively synthesized through base-catalyzed fluoroalkyl carbonate esterification of diols with bis(fluoroalkyl) carbonates (BFCs). Non-isocyanate polyurethane (NIPU) synthesis was then achieved without a catalyst through polycondensation reactions of BFBCs and a series of diamines in solvent or solvent-free conditions. Compared with the previously reported synthetic methods of NIPUs, this method has the distinct advantage of synthesizing a wide variety of NIPUs including new and commercially available conventional PUs. This method allows the arbitrary synthesis of NIPUs with commonly available diols and diamines used in the industrial production of PUs by the conventional isocyanate method, or with original synthetic ones. Furthermore, when using a solvent, the polycondensation occurred below 100 °C to give a colorless PU having an average molecular weight of over 10000. Transparent films with the characteristic high elasticity of PU could be obtained from a proper combination of BFBC and diamine, one as the hard segment and the other as the soft segment. Then, a novel fluorinated PU was successfully synthesized from a fluoroalkylene BFBC and a diamine. The present new reaction will be a practically available production method of functional NIPUs.