University of Oulu

ACS Macro Lett. 2023, 12, 2, 147–151. Publication Date:January 13, 2023

High oxygen barrier polyester from 3,3′-bifuran-5,5′-dicarboxylic acid

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Author: Kainulainen, Tuomo P.1; Parviainen, Tomi A. O.1; Sirviö, Juho Antti2;
Organizations: 1Research Unit of Sustainable Chemistry, University of Oulu, P.O. Box 4300, FI-90014 Oulu, Finland
2Fibre and Particle Engineering Research Unit, University of Oulu, P.O. Box 4300, FI-90014 Oulu, Finland
3Laboratory of Inorganic Chemistry, Environmental and Chemical Engineering, University of Oulu, P.O. Box 4300, FI-90014 Oulu, Finland
Format: article
Version: published version
Access: open
Online Access: PDF Full Text (PDF, 1.9 MB)
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Language: English
Published: American Chemical Society, 2023
Publish Date: 2023-01-17


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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Series: ACS macro letters
ISSN: 2161-1653
ISSN-E: 2161-1653
ISSN-L: 2161-1653
Volume: 12
Issue: 2
Pages: 147 - 151
DOI: 10.1021/acsmacrolett.2c00743
Type of Publication: A1 Journal article – refereed
Field of Science: 116 Chemical sciences
Funding: This work was supported by University of Oulu Proof of Concept funding. The Finnish Cultural Foundation and Magnus Ehrnrooth foundation are acknowledged for a personal working grant (T.P.K.).
Copyright information: © 2023 The Authors. Published by American Chemical Society. This article is published under a CC BY licence.