High oxygen barrier polyester from 3,3′-bifuran-5,5′-dicarboxylic acid
Kainulainen, Tuomo P.; Parviainen, Tomi A. O.; Sirviö, Juho Antti; McGeachie, Liam J. R.; Heiskanen, Juha P. (2023-01-13)
ACS Macro Lett. 2023, 12, 2, 147–151. Publication Date:January 13, 2023 https://doi.org/10.1021/acsmacrolett.2c00743
© 2023 The Authors. Published by American Chemical Society. This article is published under a CC BY licence.
https://creativecommons.org/licenses/by/4.0/
https://urn.fi/URN:NBN:fi-fe202301173324
Tiivistelmä
Abstract
An exceptional oxygen barrier polyester prepared from a new biomass-derived monomer, 3,3′-bifuran-5,5′-dicarboxylic acid, is reported. When exposed to air, the furan-based polyester cross-links and gains O2 permeability 2 orders of magnitude lower than initially, resulting in performance comparable to the best polymers in this class, such as ethylene-vinyl alcohol copolymers. The cross-links hinder the crystallization of amorphous samples, also rendering them insoluble. The process was observable via UV–vis measurements, which showed a gradual increase of absorbance between wavelengths of 320 and 520 nm in free-standing films. The structural trigger bringing about these changes appears subtle: the polyester containing 5,5′-disubstituted 3,3′-bifuran moieties cross-linked, whereas the polyester with 5,5′-disubstituted 2,2′-bifuran moieties was inert. The 3,3′-bifuran-based polyester is effectively a semicrystalline thermoplastic, which is slowly converted into a cross-linked material with intriguing material properties once sufficiently exposed to ambient air.
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