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1. Microstructural consequences of isothermal crystallization in homo- and co-polyesters based on 2,5- and 2,4-furandicarboxylic acid

Author

Aurélie Bourdet, Clément Fosse, Marie-Rose Garda, Shanmugam Thiyagarajan, Laurent Delbreilh, Antonella Esposito, Eric Dargent, Groupe de physique des matériaux (GPM), Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche sur les Matériaux Avancés (IRMA), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), and Normandie Université (NU)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS)

Subjects
[PHYS]Physics [physics], Polymers and Plastics, Organic Chemistry, Materials Chemistry
Abstract

International audience; Different position isomers of furandicarboxylic acid (FDCA) can be obtained from the biomass by a Henkel disproportionation reaction. 2,5- and 2,4-FDCA are obtained in amounts that are large enough to be used for the synthesis of polyethylene furanoate (PEF). The homopolyesters obtained with ethylene glycol (EG) and either 2,5- or 2,4-FDCA have a completely different crystallization behavior, for 2,5-PEF can crystallize whereas 2,4-PEF cannot, even after very long annealing times. The synthesis of random copolyesters with EG and different ratios of 2,5/2,4-FDCA may therefore allow to tune PEF crystallization ability. The partial replacement of 2,5-FDCA by its position isomer could help disrupting crystallinity analogously to what happens when EG is partially replaced by cyclohexane dimethanol (CHDM) in glycolyzed polyethylene terephthalate (PETg). This work investigates the thermal behavior of the homopolyester 2,5-PEF and the microstructural consequences of copolymerization (replacement of small amounts of 2,5-FDCA with 2,4-FDCA). Crystallization is performed in isothermal conditions after cooling down from the molten state, and investigated with both conventional DSC and Fast Scanning Calorimetry (FSC). When the amount of 2,4-FDCA-based repeating units is low (10 and 15 mol %), crystallization still occurs but with an increased induction time. Neither the crystalline nor the rigid amorphous fractions are significantly affected by copolymerization. Due to multiple and complex microstructural reorganizations observed at relatively slow heating rates, conventional DSC is inaccurate and does not provide a reliable microstructural depiction of these polyesters. The use of FSC is recommended, for it allows to obtain a better characterization of the quality and thermal stability of the formed crystals.

Published
2023

2. Molecular Mobility in Amorphous Biobased Poly(ethylene 2,5-furandicarboxylate) and Poly(ethylene 2,4-furandicarboxylate)

Author

Laurent Delbreilh, Frédéric Affouard, Shanmugam Thiyagarajan, Aurélie Bourdet, Antonella Esposito, Eric Dargent, Rutger J. I. Knoop, Groupe de physique des matériaux (GPM), Centre National de la Recherche Scientifique (CNRS)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU), Wageningen Food & Biobased Res, Bornse Weilanden 9, NL-6708 WG Wageningen, Netherlands, Unité Matériaux et Transformations - UMR 8207 (UMET), Centre National de la Recherche Scientifique (CNRS)-Université de Lille-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)-Institut National de la Recherche Agronomique (INRA), Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche sur les Matériaux Avancés (IRMA), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS), Institut National de la Recherche Agronomique (INRA)-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), and Institut de Chimie du CNRS (INC)-Institut National de la Recherche Agronomique (INRA)-Centre National de la Recherche Scientifique (CNRS)-Université de Lille-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)

Subjects
Materials science, Ethylene, Polymers and Plastics, 02 engineering and technology, Activation energy, 010402 general chemistry, 01 natural sciences, Inorganic Chemistry, chemistry.chemical_compound, Differential scanning calorimetry, BBP Sustainable Chemistry & Technology, Materials Chemistry, Life Science, ComputingMilieux_MISCELLANEOUS, chemistry.chemical_classification, Organic Chemistry, Polymer, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Amorphous solid, Polyester, Chemical engineering, chemistry, [PHYS.COND.CM-MS]Physics [physics]/Condensed Matter [cond-mat]/Materials Science [cond-mat.mtrl-sci], Relaxation (physics), 0210 nano-technology, Glass transition
Abstract

Among all the emergent biobased polymers, poly(ethylene 2,5-furandicarboxylate) (2,5-PEF) seems to be particularly interesting for packaging applications. This work is focused on the investigation of the relaxation dynamics and the macromolecular mobility in totally amorphous 2,5-PEF as well as in the less studied poly(ethylene 2,4-furandicarboxylate) (2,4-PEF). Both biopolymers were investigated by differential scanning calorimetry and dielectric relaxation spectroscopy in a large range of temperatures and frequencies. The main parameters describing the relaxation dynamics and the molecular mobility in 2,5-PEF and 2,4-PEF, such as the glass transition temperature, the temperature dependence of the α and β relaxation times, the fragility index, and the apparent activation energy of the secondary relaxation, were determined and discussed. 2,5-PEF showed a higher value of the dielectric strength as compared to 2,4-PEF and other well-known polyesters, such as poly(ethylene terephthalate), which was confirmed by molecular dynamics simulations. According to the Angell's classification of glass-forming liquids, amorphous PEFs behave as stronger glass-formers in comparison with other polyesters, which may be correlated to the packing efficiency of the macromolecular chains and therefore to the free volume and the barrier properties.

Published
2018

3. Synthesis and thermal properties of bio-based copolyesters from the mixtures of 2,5- and 2,4-furandicarboxylic acid with different diols

Author

Rutger J. I. Knoop, Daan S. van Es, Shanmugam Thiyagarajan, Aurélie Bourdet, Eric Dargent, Jacco van Haveren, Antonella Esposito, Willem Vogelzang, Michael A. Meijlink, Wageningen Food & Biobased Res, Bornse Weilanden 9, NL-6708 WG Wageningen, Netherlands, Groupe de physique des matériaux (GPM), Centre National de la Recherche Scientifique (CNRS)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU), Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche sur les Matériaux Avancés (IRMA), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), and Normandie Université (NU)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS)

Subjects
General Chemical Engineering, Bio based, 02 engineering and technology, Activation energy, 010402 general chemistry, 01 natural sciences, [SPI.MAT]Engineering Sciences [physics]/Materials, chemistry.chemical_compound, BBP Sustainable Chemistry & Technology, Furan, Thermal, Environmental Chemistry, Organic chemistry, Biobased Products, ComputingMilieux_MISCELLANEOUS, VLAG, MT-TGA, Renewable Energy, Sustainability and the Environment, General Chemistry, 021001 nanoscience & nanotechnology, mixing law, 0104 chemical sciences, Polyester, activation energy, chemistry, [PHYS.COND.CM-MS]Physics [physics]/Condensed Matter [cond-mat]/Materials Science [cond-mat.mtrl-sci], 0210 nano-technology, FDCA isomers, Henkel reaction, [PHYS.COND.CM-SCM]Physics [physics]/Condensed Matter [cond-mat]/Soft Condensed Matter [cond-mat.soft]
Abstract

Recent works highlighted how interesting are the properties of furan-based polyesters. Most of the attention has been focused on the homopolyester obtained with 2,5-furandicarboxylic acid and ethylene glycol, but other possibilities exist, which could help in tuning the final properties by carefully selecting the nature and proportion of the initial building blocks. This work reports the synthesis and properties (thermal stability, activation energy for thermal decomposition, glass transition temperature, and aptitude to crystallize) of three series of polyesters obtained by combining various amounts of two isomers of furandicarboxylic acid with different linear aliphatic diols, such as ethylene glycol, 1,3-propanediol, and 1,4-butanediol. This approach provided homopolymers and copolymers with high molecular weights, good thermal stability, broad processing windows, and a thermal behavior that can be tuned both in terms of glass transition temperature and crystallinity. In most cases, the mixtures of 2,5- A nd 2,4-isomers obtained during the Henkel disproportionation reaction can be directly used to synthetize furan-based copolyesters with good properties without the downstream processing typically performed to separate the isomers prior to polymerization, which may considerably reduce the time and costs for biomass valorization.

Published
2019

4. Determination of the equilibrium enthalpy of melting of two-phase semi-crystalline polymers by fast scanning calorimetry

Author

Laurent Delbreilh, Clément Fosse, Shanmugam Thiyagarajan, Rutger J. I. Knoop, Aurélie Bourdet, Eric Dargent, Nicolas Delpouve, Esteve Ernault, Antonella Esposito, Groupe de physique des matériaux (GPM), Centre National de la Recherche Scientifique (CNRS)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU), Wageningen Food & Biobased Res, Bornse Weilanden 9, NL-6708 WG Wageningen, Netherlands, Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche sur les Matériaux Avancés (IRMA), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), and Normandie Université (NU)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Materials science, Enthalpy, Thermodynamics, 02 engineering and technology, Calorimetry, Enthalpy of melting, 01 natural sciences, law.invention, [SPI.MAT]Engineering Sciences [physics]/Materials, PBF, Crystallinity, Differential scanning calorimetry, law, BBP Sustainable Chemistry & Technology, Physical and Theoretical Chemistry, Crystallization, Instrumentation, ComputingMilieux_MISCELLANEOUS, chemistry.chemical_classification, [PHYS]Physics [physics], Fast scanning calorimetry, Polymer, 021001 nanoscience & nanotechnology, Condensed Matter Physics, Microstructure, PEF, 010406 physical chemistry, 0104 chemical sciences, Amorphous solid, chemistry, [PHYS.COND.CM-MS]Physics [physics]/Condensed Matter [cond-mat]/Materials Science [cond-mat.mtrl-sci], Rigid amorphous fraction, 0210 nano-technology, [PHYS.COND.CM-SCM]Physics [physics]/Condensed Matter [cond-mat]/Soft Condensed Matter [cond-mat.soft]
Abstract

The equilibrium enthalpy of melting ΔHm0 [J·g−1] is an extrapolated thermodynamic quantity attributed to crystallizable macromolecules and widely used to characterize polymers in their semi-crystalline state, for it allows estimating the degree of crystallinity by direct comparison with the enthalpy of melting obtained from differential scanning calorimetry. ΔHm0 is typically obtained by cross-comparing the results obtained by at least two techniques. This work proposes a simplified experimental protocol to determine ΔHm0 by the use of Fast Scanning Calorimetry (FSC). This approach applies to any crystallizable polymer for which a specific microstructure can be obtained (i.e. a two-phase semi-crystalline microstructure with a negligible amount of rigid amorphous fraction) and that can also be quenched to its fully amorphous state. Such a two-phase microstructure can be obtained on nanoscale samples through an annealing process performed in situ on the FSC sensor at crystallization temperatures as close as possible to the melting temperature. The enthalpy of melting is then evaluated from the two-phase model for different crystallization times (i.e. different crystallinities) and the ΔHm0 is obtained by extrapolating the data to the 100% crystalline state. This procedure was applied on samples whose ΔHm0 values are already available in the literature, but also on more recent biobased polyesters whose thermal properties are still under investigations.

Published
2019

5. Molecular mobility in amorphous biobased copolyesters obtained with 2,5- and 2,4-furandicarboxylate acid

Author

Antonella Esposito, Laurent Delbreilh, Shanmugam Thiyagarajan, Steven Araujo, Aurélie Bourdet, Eric Dargent, Groupe de physique des matériaux (GPM), Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche sur les Matériaux Avancés (IRMA), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS), Wageningen Food & Biobased Research, and Wageningen University and Research [Wageningen] (WUR)

Subjects
Polymers and Plastics, Cooperativity, Relaxation processes, 02 engineering and technology, Activation energy, 010402 general chemistry, 01 natural sciences, [SPI.MAT]Engineering Sciences [physics]/Materials, chemistry.chemical_compound, Differential scanning calorimetry, Poly(ethylene furandicarboxylate) (PEF), BBP Sustainable Chemistry & Technology, Materials Chemistry, Fragility, Temperature-modulated differential scanning calorimetry (MT-DSC), ComputingMilieux_MISCELLANEOUS, [PHYS]Physics [physics], chemistry.chemical_classification, Terephthalic acid, Thermo-stimulated depolarization current (TSDC), Copolymers, Position isomerism, Organic Chemistry, Relaxation (NMR), Polymer, 021001 nanoscience & nanotechnology, 0104 chemical sciences, chemistry, [PHYS.COND.CM-MS]Physics [physics]/Condensed Matter [cond-mat]/Materials Science [cond-mat.mtrl-sci], Physical chemistry, 0210 nano-technology, Glass transition, [PHYS.COND.CM-SCM]Physics [physics]/Condensed Matter [cond-mat]/Soft Condensed Matter [cond-mat.soft], Dielectric relaxation spectroscopy (DRS), Ethylene glycol
Abstract

Poly(ethylene 2,5-furandicarboxylate) (2,5-PEF) is one of the most credible biobased alternative to poly (ethylene terephthalate) (PET). The Henkel disproportionation reaction that leads to furandicarboxylic acid (FDCA) provides three position isomers: 2,5-FDCA (obtained with the highest yield), 2,4-FDCA (so far considered as a by-product), and 3,4-FDCA (traces). The copolymerization of the two main isomers of FDCA with a diol, e.g. ethylene glycol (EG), is an interesting approach to obtain a family of furan-based biopolymers with adjusted physical properties. This work investigates the molecular mobility of three copolymers obtained with EG and ratios of 2,5-FDCA and 2,4-FDCA ensuring the complete disruption of crystallization (90:10, 85:15 and 50:50 mol % of 2,5:2,4 FDCA), as compared to the homopolymers 2,5-PEF and 2,4-PEF. The molecular mobility was investigated by cross-comparing the results obtained by Modulated-Temperature Differential Scanning Calorimetry (MT-DSC), Dielectric Relaxation Spectroscopy (DRS) and Thermo-Stimulated Depolarization Currents (TSDC), with the aim of evaluating the local and segmental molecular mobilities, their activation energies, as well as the temperature dependence of the relaxation time and of the cooperatively rearranging regions at the glass transition. The furan ring in 2,5-FDCA (2,5-PEF) has a rotation axis that is less linear compared to the benzene ring in terephthalic acid (PET), with consequences on the ring-flipping mechanisms. 2,5-FDCA and 2,4-FDCA differ by the position of the carbonyl groups on the furan ring, which adds asymmetry to non-linearity. The incorporation of 2,4-FDCA-based units into a polymer backbone mainly constituted of 2,5-FDCA-based repeating units is responsible for longer relaxation times associated with the local β relaxation processes, no striking effects on the kinetic fragility index m, no obvious effects on cooperativity (a slightly increase in the cooperativity length is observed in the liquid state), no effects on the activation energy for the segmental α relaxation in the liquid state, and a decrease in the activation energy in the glassy state.

Published
2021

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