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)

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.

Copolyesters developed from bio‐based 2,5‐furandicarboxylic acid: Synthesis, sequence distribution, mechanical, and barrier properties of poly(propylene‐co‐1,4‐cyclohexanedimethylene 2,5‐furandicarboxylate)s

“…Beside, their average weight‐average molecular weight ( M w ) was measured by gel permeation chromatography (GPC) and determined to be varied from 30 400 to 61 800 g mol −1 with the molar‐mass dispersity ( Ð ) of 1.38–1.69. The M w of PPCFs synthesized in this work was similar to the FDCA‐based copolyesters reported in previous literatures …”

“…Most of the studies have been focused on the FDCA‐based polyesters. Taking different diols, a large quantity of polyesters, such as poly(octylene 2,5‐furandicarboxylate) (POF), poly (ethylene 2,5‐furandicarboxylate) (PEF), poly(propylene 2,5‐furandicarboxylate) (PPF), poly(butylene 2,5‐furandicarboxylate) (PBF), poly(decylene‐2,5‐furanote) (PDeF), and poly(hexamethylene 2,5‐furandicarboxylate) (PHF) have been synthesized. Among them, PEF, PPF, and PBF demonstrate excellent barrier properties, good thermal stability, and mechanical properties .…”

Co-Polymers based on Poly(1,4-butylene 2,5-furandicarboxylate) and Poly(propylene oxide) with Tuneable Thermal Properties: Synthesis and Characterization

“…Some examples of polyesters synthesized from FDCA are poly(ethylene 2,5-furandicarboxylate) (PEF) [3] and poly(1,4-butylene 2,5-furandicarboxylate) (PBF), among others, with similar properties to those of their TPA counterparts [4,5,6,7,8,9,10,11] or even enhanced properties such as for example barrier properties or degradability under enzymatic conditions [12,13]. Furthermore, several other diols besides linear ones have been explored to prepare FDCA-based homopolymers, namely branched diols such as 1,2-propanediol, 2,3-butanediol, 2-methyl-1,3-propanediol and 2,2-dimethyl-1,3-propanediol [14,15,16,17,18,19,20]. The ensuing materials presented even higher T g s than those of their corresponding homopolyesters synthesized with linear diols with the same number of carbon atoms.…”

Poly(1,4-cyclohexanedimethylene 2,6-naphthalate) polyester with high melting point: Effect of different synthesis methods on molecular weight and properties

“…Since the first in-depth study on the degradation of PET [17], it is generally agreed upon that polyesters with beta-hydrogens on their structure follow mainly the β-heterolytic scission pathway during thermal degradation, along with radical and α-scission reaction in a smaller extent and only at higher temperatures [18][19][20][21][22][23][24][25][26][27][28]. In this study, Py/GC-MS was employed as a tool to investigate the reasons behind the differences on the thermal stability of the PCHDMN polyesters.…”