Isosorbide and 2,5-Furandicarboxylic Acid Based (Co)Polyesters: Synthesis, Characterization, and Environmental Degradation

Chaima Bouyahya; Rafael Patrício; Ana Paço; Mafalda S Lima; Ana C Fonseca; Teresa Rocha-Santos; Mustapha Majdoub; Armando J D Silvestre; Andreia F Sousa

doi:10.3390/polym14183868

Isosorbide and 2,5-Furandicarboxylic Acid Based (Co)Polyesters: Synthesis, Characterization, and Environmental Degradation

Polymers (Basel). 2022 Sep 15;14(18):3868. doi: 10.3390/polym14183868.

Authors

Affiliations

¹ CICECO-Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.
² Laboratoire des Interfaces et Matériaux Avancés, Université de Monastir, Monastir 5000, Tunisia.
³ Centre for Environmental and Marine Studies (CESAM), Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.
⁴ Centre for Mechanical Engineering, Materials and Processes, Department of Chemical Engineering, University of Coimbra Rua Sílvio Lima-Polo II, 3030-790 Coimbra, Portugal.

Abstract

Poly(2,5-furandicarboxylate)s incorporating aliphatic moieties represent a promising family of polyesters, typically entirely based on renewable resources and with tailored properties, notably degradability. This study aims to go beyond by developing poly(isosorbide 2,5-furandicarboxylate-co-dodecanedioate) copolyesters derived from isosorbide (Is), 2,5-furandicarboxylic acid (FDCA), and 1,12-dodecanedioic acid (DDA), and studying their degradation under environmental conditions, often overlooked, namely seawater conditions. These novel polyesters have been characterized in-depth using ATR-FTIR, ¹H, and ¹³C NMR and XRD spectroscopies and thermal analysis (TGA and DSC). They showed enhanced thermal stability (up to 330 °C), and the glass transition temperature increased with the content of FDCA from ca. 9 to 60 °C. Regarding their (bio)degradation, the enzymatic conditions lead to the highest weight loss compared to simulated seawater conditions, with values matching 27% vs. 3% weight loss after 63 days of incubation, respectively. Copolymerization of biobased FDCA, Is, and DDA represents an optimal approach for shaping the thermal/(bio)degradation behaviors of these novel polyesters.

Keywords: 2,5-furandicarboxylic acid; biobased (co)polyesters; environmental degradation; isosorbide.

Grants and funding

This research was funded by FCT—Fundação para a Ciência e a Tecnologia/MEC (PIDDAC), UIDB/50011/2020 and UIDP/50011/2020. This research is also sponsored by FEDER funds through the program COMPETE—Programa Operacional Factores de Competitividade—and by national funds through the FCT under the project UID/EMS/00285/2020. This publication was also supported by COST Action FUR4Sustain—European network of FURan based chemicals and materials FOR a Sustainable development, CA18220. C.B. also acknowledges FUR4Sustain COST Action for a Short-Term Scientific Mission (STSM). This work was developed within the scope of CICECO—Aveiro Institute of Materials (UIDB/50011/2020 and UIDP/50011/2020) and LA/P/0006/2020, financed by national funds through the FCT—Fundação para a Ciência e a Tecnologia/MEC (PIDDAC). The FCT is also acknowledged for the research contract under Scientific Employment Stimulus to A.F.S. (CEECIND/02322/2020).