Synthesis and Characterization of Bio-Based Polyesters: Poly(2-methyl-1,3-propylene-2,5-furanoate), Poly(isosorbide-2,5-furanoate), Poly(1,4-cyclohexanedimethylene-2,5-furanoate)

Zoi Terzopoulou; Nejib Kasmi; Vasilios Tsanaktsis; Nikolaos Doulakas; Dimitrios N Bikiaris; Dimitris S Achilias; George Z Papageorgiou

doi:10.3390/ma10070801

Synthesis and Characterization of Bio-Based Polyesters: Poly(2-methyl-1,3-propylene-2,5-furanoate), Poly(isosorbide-2,5-furanoate), Poly(1,4-cyclohexanedimethylene-2,5-furanoate)

Materials (Basel). 2017 Jul 14;10(7):801. doi: 10.3390/ma10070801.

Authors

Zoi Terzopoulou¹, Nejib Kasmi², Vasilios Tsanaktsis³, Nikolaos Doulakas⁴, Dimitrios N Bikiaris⁵, Dimitris S Achilias⁶, George Z Papageorgiou⁷

Affiliations

¹ Laboratory of Polymer Chemistry and Technology, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki GR-541 24, Greece. terzoe@gmail.com.
² Laboratory of Polymer Chemistry and Technology, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki GR-541 24, Greece. nejibkasmi@gmail.com.
³ Laboratory of Polymer Chemistry and Technology, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki GR-541 24, Greece. vt-vasilis@windowslive.com.
⁴ Laboratory of Polymer Chemistry and Technology, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki GR-541 24, Greece. doulakas@gmail.com.
⁵ Laboratory of Polymer Chemistry and Technology, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki GR-541 24, Greece. dbic@chem.auth.gr.
⁶ Laboratory of Polymer Chemistry and Technology, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki GR-541 24, Greece. axilias@chem.auth.gr.
⁷ Department of Chemistry, University of Ioannina, Ioannina GR-54110, Greece. gzpap@cc.uoi.gr.

Abstract

In the present study, three new biobased furanoate polyesters with potential use in food packaging applications, named poly(isosorbide furanoate) (PIsF), poly(methyl-propylene furanoate) (PMePF) and poly(1,4-cyclohexane-dimethylene 2,5-furanoate) (PCHDMF) were synthesized. As monomers for the preparation of the polyesters, 2,5-furandicarboxylic acid (FDCA) and diols with irregular or complicated structure were used, including isosorbide (IS), 2-methyl-1,3-propanediol (MPD) and 1,4-cyclohexane-dimethanol (CHDM). The polymerization process was carried out via melt polycondensation method. The structural characteristics and thermal behavior of the polymers were studied. The kinetic fragility of the amorphous phase of the polymers was evaluated. The thermal degradation was studied by means of thermogravimetry and a pyrolysis Py-GC/MS (Pyrolysis-Gas Chromatography/Mass Spectroscopy) system to estimate the degradation mechanism.

Keywords: complicated structure diols; furanoate polyesters; synthesis; thermal properties.