High barrier biosourced polyester from dimethyl [2,2′-bifuran]-5,5′-dicarboxylate

• Published in: Polymer (Guilford) Vol. 191; p. 122258
• Main Authors: Edling, H. Eliot, Sun, Hua, Paschke, Edward, Schiraldi, David A., Tanko, James M., Paradzinsky, Mark, Turner, S. Richard
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 16.03.2020; Elsevier BV
• Subjects: Antioxidants; Crystallization; Elongation; Ethylene; Glass transition temperature; Information processing; Monomers; Oxidation; Oxygen; Oxygen barrier; Polycondensation; Polyesters; Polymers; Reduction; Terephthalate; Transition temperatures; Polyesters; Polycondensation; Oxygen barrier
• ISSN: 0032-3861; 1873-2291
• DOI: 10.1016/j.polymer.2020.122258

Poly (ethylene 2,2′-bifuran-5,5′dicarboxylate) (PEBF) is a new biosourced polyester recently reported to have significant enhancement of oxygen barrier properties and glass transition temperature when compared to poly (ethylene terephthalate). We report herein our independent studies on the polymerization and properties of this new polyester. Our findings are contrasted to an earlier report. While the Tg of 106–108 °C was confirmed to be consistent with the early data, we observed crystallization on both cooling and heating cycles in the DSC which were not previously observed, higher tensile elongation to break values, and significantly lower oxygen permeabilities compared to the earlier report. Preliminary uniaxial orientation experiments indicate that this polymer is a good candidate for biaxial orientation processing. We discovered that both the monomer, dimethyl-2,2′-bifuran-5,5′-dicarboxylate (BFE), and the polymer are subject to thermal oxidation which was explored with cyclic voltammetry on the monomer. Experiments with added antioxidant during the polycondensation show marked reduction in the thermal oxidation as observed by color reduction and enhanced stability to melt processing. [Display omitted] •High oxygen barrier poly (ethylene 2,2′-bifuran-5,5′dicarboxylate) (PEBF) prepared by standard melt phase polyesterification.•DSC on PEBF from these polyesterifications revealed a strong crystallization peak on cooling.•High oxygen barrier and high elongations and modulus values were observed.•High oxygen barrier the result of low diffusion coefficient.•Use of an antioxidant mitigated thermal oxidative instability.