Synthesis and Characterization of Poly(2,5-furan dicarboxylate)s Based on a Variety of Diols

Abstract

Novel polyesters from renewable resources based on 2,5-dicarboxylic acid and several dials were synthesized and characterized using different polycondensation techniques. The aliphatic dials were sufficiently volatile to allow the use of polytransesterifications, which gave high-molecular weight semicrystalline materials with good thermal stability. In particular, the polyester based on ethylene glycol displayed properties comparable with those of its aromatic counterpart, poly(ethylene terephthalate), namely, the most important industrial polyester. The use of isosorbide gave rise to amorphous polymers with very stiff chains and hence a high glass transition temperature and an enhanced thermal stability. The interfacial polycondensation between the acid dichloride and hydroquinone produced a semicrystalline material with features similar to those of entirely aromatic polyesters, characterized essentially by the absence of melting and poor solubility, both associated with their remarkable chain rigidity. The replacement of hydroquinone with the corresponding benzylic dial was sufficient to provide a more tractable polyester. This study provided ample evidence in favor of the exploitation of furan monomers as renewable alternatives to fossil-based aromatic homologs. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49: 3759-3768, 2011