Enzymatically catalyzed furan-based copolyesters containing dilinoleic diol as a building block

Martyna Sokołowska; Jagoda Nowak-Grzebyta; Ewa Stachowska; Piotr Miądlicki; Magdalena Zdanowicz; Beata Michalkiewicz; Miroslawa El Fray

doi:10.1039/d3ra03885h

Enzymatically catalyzed furan-based copolyesters containing dilinoleic diol as a building block

RSC Adv. 2023 Jul 24;13(32):22234-22249. doi: 10.1039/d3ra03885h. eCollection 2023 Jul 19.

Authors

Martyna Sokołowska¹, Jagoda Nowak-Grzebyta², Ewa Stachowska², Piotr Miądlicki³, Magdalena Zdanowicz⁴, Beata Michalkiewicz³, Miroslawa El Fray¹

Affiliations

¹ West Pomeranian University of Technology, Szczecin, Faculty of Chemical Technology and Engineering, Department of Polymer and Biomaterials Science Al. Piastow 45 71-311 Szczecin Poland mirfray@zut.edu.pl.
² Poznan University of Technology, Faculty of Mechanical Engineering Ul. Piotrowo 3 60-965 Poznan Poland.
³ West Pomeranian University of Technology, Szczecin, Faculty of Chemical Technology and Engineering, Engineering of Catalytic and Sorbent Materials Department Al. Piastow 45 71-311 Szczecin Poland.
⁴ West Pomeranian University of Technology in Szczecin, Faculty of Food Sciences, Center of Bioimmobilisation and Innovative Packaging Materials Ul. Janickiego 35 71-270 Szczecin Poland.

Abstract

A more environmentally friendly method for creating sustainable alternatives to traditional aromatic-aliphatic polyesters is a valuable step towards resource-efficiency optimization. A library of furan-based block copolymers was synthesized via temperature-varied two-step polycondensation reaction in diphenyl ether using Candida antarctica lipase B (CAL-B) as a biocatalyst where dimethyl 2,5-furandicarboxylate (DMFDCA), α,ω-aliphatic linear diols (α,ω-ALD), and bio-based dilinoleic diol (DLD) were used as the starting materials. Nuclear magnetic spectroscopy (¹H and ¹³C NMR), Fourier transform spectroscopy (FTIR) and size exclusion chromatography (SEC) were used to analyze the resulting copolymers. Additionally, crystallization behavior and thermal properties were studied using X-ray diffraction (XRD), digital holographic microscopy (DHM), and differential scanning microscopy (DSC). Finally, oxygen transmission rates (OTR) and dynamic mechanical analysis (DMTA) of furan-based copolyesters indicated their potential for medical packaging.