University of Oulu

Kainulainen, T., Hukka, T., Özeren, H., Sirviö, J., Hedenqvist, M. & Heiskanen, J. (2020) Utilizing furfural-based bifuran diester as monomer and comonomer for high-performance bioplastics : properties of poly(butylene furanoate), poly(butylene bifuranoate), and their copolyesters. Biomacromolecules, 21, 2, 743-752. https://doi.org/10.1021/acs.biomac.9b01447

Utilizing furfural-based bifuran diester as monomer and comonomer for high-performance bioplastics : properties of poly(butylene furanoate), poly(butylene bifuranoate), and their copolyesters

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Author: Kainulainen, Tuomo P.1; Hukka, Terttu I.2; Özeren, Hüsamettin D.3;
Organizations: 1Research Unit of Sustainable Chemistry, University of Oulu, P.O. Box 4300, FI-90014 Oulu, Finland
2Laboratory of Chemistry and Bioengineering, Tampere University of Technology, P.O. Box 541, FI-33101 Tampere, Finland
3Department of Fibre and Polymer Technology, School of Engineering Sciences in Chemistry, Biotechnology and Health, KTH Royal Institute of Technology, SE-100 44, Stockholm, Sweden
4Fibre and Particle Engineering Research Unit, University of Oulu, P.O. Box 4300, FI-90014 Oulu, Finland
Format: article
Version: accepted version
Access: embargoed
Persistent link: http://urn.fi/urn:nbn:fi-fe202001243242
Language: English
Published: American Chemical Society, 2020
Publish Date: 2020-12-02
Description:

Abstract

Two homopolyesters and a series of novel random copolyesters were synthesized from two bio-based diacid esters, dimethyl 2,5-furandicarboxylate, a well-known renewable monomer, and dimethyl 2,2′-bifuran-5,5′-dicarboxylate, a more uncommon diacid based on biochemical furfural. Compared to homopolyesters poly(butylene furanoate) (PBF) and poly(butylene bifuranoate) (PBBf), their random copolyesters differed dramatically in that their melting temperatures were either lowered significantly or they showed no crystallinity at all. However, the thermal stabilities of the homopolyesters and the copolyesters were comparable. Based on tensile tests from amorphous film specimens, it was concluded that the elastic moduli, tensile strengths, and elongation at break values for all copolyesters were similar as well, irrespective of the furan:bifuran molar ratio. Tensile moduli of approximately 2 GPa and tensile strengths up to 66 MPa were observed for amorphous film specimens prepared from the copolyesters. However, copolymerizing bifuran units into PBF allowed the glass transition temperature to be increased by increasing the amount of bifuran units. Besides enhancing the glass transition temperatures, the bifuran units also conferred the copolyesters with significant UV absorbance. This combined with the highly amorphous nature of the copolyesters allowed them to be melt-pressed into highly transparent films with very low ultraviolet light transmission. It was also found that furan–bifuran copolyesters could be as effective, or better, oxygen barrier materials as neat PBF or PBBf, which themselves were found superior to common barrier polyesters such as PET.

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Series: Biomacromolecules
ISSN: 1525-7797
ISSN-E: 1526-4602
ISSN-L: 1525-7797
Volume: 21
Issue: 2
Pages: 743 - 752
DOI: 10.1021/acs.biomac.9b01447
OADOI: https://oadoi.org/10.1021/acs.biomac.9b01447
Type of Publication: A1 Journal article – refereed
Field of Science: 116 Chemical sciences
Subjects:
Funding: The Alfred Kordelin foundation and Magnus Ehrnrooth foundation are acknowledged for providing funding. University of Oulu is thanked for providing financial support (Proof of Concept grant). Dr. Tao Hu is thanked for providing guidance in obtaining the XRD data.
Copyright information: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Biomacromolecules, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.biomac.9b01447.