University of Oulu

Kainulainen, T. P., Ahmed, A. M., Antti Sirviö, J., & Heiskanen, J. P. (2023). Sulfone-bridged difuran polyesters. European Polymer Journal, 200, 112540.

Sulfone-bridged difuran polyesters

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Author: Kainulainen, Tuomo P.1; Ahmed, Asmaa M.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
Format: article
Version: published version
Access: open
Online Access: PDF Full Text (PDF, 0.9 MB)
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Language: English
Published: Elsevier, 2023
Publish Date: 2023-10-31


Oxidation of 5,5’-sulfanediyldi(furan-2-carboxylic acid) in acetic acid with aqueous hydrogen peroxide was used to prepare a new dicarboxylic monomer with a central sulfone group flanked by two biomass-derived furan rings. The new sulfone monomer was reacted with ethylene glycol, 1,3-propanediol, 1,4-butanediol, and 1,5-pentanediol to prepare new homopolyesters. Of these diols, 1,5-pentanediol yielded polyester with the most favorable properties in terms of processability and appearance. It could also be recycled back into the starting monomer under mild conditions. Using 1,5-pentanediol, a copolyester containing a 1:1 mixture of sulfone and sulfide difuran units was also prepared for testing alongside the corresponding sulfone difuran homopolyester. From measurements carried out on film samples of these two new materials, it was found that the new sulfone monomer will lead to polyester materials with high glass transition temperatures, high tensile stiffnesses, and low O₂ permeability. The nature of the side reactions related to the difuran sulfone moiety under high temperatures remained unclear, as thermogravimetric analysis indicated relatively good stability characteristics and the monomer appeared relatively stable even at high temperatures.

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Series: European polymer journal
ISSN: 0014-3057
ISSN-E: 1873-1945
ISSN-L: 0014-3057
Volume: 200
Article number: 112540
DOI: 10.1016/j.eurpolymj.2023.112540
Type of Publication: A1 Journal article – refereed
Field of Science: 116 Chemical sciences
Funding: Magnus Ehrnrooth foundation is acknowledged for providing a personal working grant for T.P.K. Jenny and Antti Wihuri Foundation is acknowledged for personal working grant for A.M.A. The work was supported by the University of Oulu Proof of Concept fund.
Copyright information: © 2023 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license (