Unravelling the para- and ortho-benzene substituent effect on the glass transition of renewable wholly (hetero-)aromatic polyesters bearing 2,5-furandicarboxylic moieties

Zaidi, S. M. Javid; Soares, M.J.; Bougarech, Abdelkader; Thiyagarajan, Shanmugam; Guigo, Nathanaël; Abid, Souhir; Abid, Majdi; Silvestre, Armando J. D.; Sousa, Andreia F.

doi:10.1016/j.eurpolymj.2021.110413

Cited by 13 publications

(6 citation statements)

References 42 publications

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“…DMTA traces (Table 2 and Figure S4 of Supplementary material) clearly illustrate this, showing a drastic increase in T g , from −6.3 up to 137.9 • C, along with the F content increase and related stiffness. In line with previous results, we noticed that DMTA results tend to be higher than those obtained by DSC [35]. Moreover, in some of the tan δ traces, it was also possible to observe the β transition and the onset of the melting event.…”

Section: Crystallization Behavior and Thermal Propertiessupporting

confidence: 91%

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

et al. 2022

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Poly(2,5-furananedicarboxylate)s incorporating aliphatic moieties represents 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.

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Section: Crystallization Behavior and Thermal Propertiessupporting

confidence: 91%

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

et al. 2022

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“…FDCA has been exploited in both fully aromatic polymers (mainly polyesters) [ 16 , 17 , 18 , 19 ] as well as in aliphatic-furanic ones [ 20 , 21 , 22 , 23 , 24 ]. The most popular class is undoubtedly the linear-aliphatic polyesters [ 12 ], with poly(ethylene 2,5-furandicarboxylate) (PEF) and poly(1,3-propylene 2,5-furandicarboxylate) (PPF) occupying a preeminent place as biobased alternatives to the petrochemical PET in films, fibers, and packaging [ 5 ].…”

Section: Introductionmentioning

confidence: 99%

Highly Flexible Poly(1,12-dodecylene 5,5′-isopropylidene-bis(ethyl 2-furoate)): A Promising Biobased Polyester Derived from a Renewable Cost-Effective Bisfuranic Precursor and a Long-Chain Aliphatic Spacer

et al. 2023

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The continuous search for novel biobased polymers with high-performance properties has highlighted the role of monofuranic-based polyesters as some of the most promising for future plastic industry but has neglected the huge potential for the polymers’ innovation, relatively low cost, and synthesis easiness of 5,5′-isopropylidene bis-(ethyl 2-furoate) (DEbF), obtained from the platform chemical, worldwide-produced furfural. In this vein, poly(1,12-dodecylene 5,5′-isopropylidene -bis(ethyl 2-furoate)) (PDDbF) was introduced, for the first time, as a biobased bisfuranic long-chain aliphatic polyester with an extreme flexibility function, competing with fossil-based polyethylene. This new polyester in-depth characterization confirmed its expected structure (FTIR, 1H, and 13C NMR) and relevant thermal features (DSC, TGA, and DMTA), notably, an essentially amorphous character with a glass transition temperature of −6 °C and main maximum decomposition temperature of 340 °C. Furthermore, PDDbF displayed an elongation at break as high as 732%, around five times higher than that of the 2,5-furandicarboxylic acid counterpart, stressing the unique features of the bisfuranic class of polymers compared to monofuranic ones. The enhanced ductility combined with the relevant thermal properties makes PDDbF a highly promising material for flexible packaging.

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“…Additionally, PCF- trans 98 exhibited the shortest crystallization half time at 7 s and the best mechanical properties (1820 MPa for tensile modulus and 52 MPa for tensile strength). Other cyclic monomers were also investigated and patented such as 2,2,4,4-tetramethylcyclobutane-1,3-diol [ 70 ], dianhydrohexitols [ 71 ], hydroquinone [ 72 ], and dichloro-2,3-o-isopropylidene L-tartrate [ 73 ]. Scheme 2 shows the structure of the main rigid diols above-mentioned.…”

Section: Homo-polyesters From Fdcamentioning

confidence: 99%

Recent Progress on Bio-Based Polyesters Derived from 2,5-Furandicarbonxylic Acid (FDCA)

et al. 2022

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The big challenge today is the upgrading of sustainable materials to replace miscellaneous ones from petroleum resources. Thus, a generic bio-based building block lays the foundation of the huge bio-market to green economy. 2,5-Furandicarboxylic acid (FDCA), a rigid diacid derived from lignocellulose or fructose, represents a great potential as a contender to terephthalic acid (TPA). Recently, studies on the synthesis, modification, and functionalization of bio-based polyesters based on FDCA have attracted widespread attention. To apply furanic polyesters on engineering plastics, packaging materials, electronics, etc., researchers have extended the properties of basic FDCA-based homo-polyesters by directional copolymerization and composite preparation. This review covers the synthesis and performance of polyesters and composites based on FDCA with emphasis bedded on the thermomechanical, crystallization, barrier properties, and biodegradability. Finally, a summary of what has been achieved and the issues waiting to be addressed of FDCA-based polyester materials are suggested.

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Unravelling the para- and ortho-benzene substituent effect on the glass transition of renewable wholly (hetero-)aromatic polyesters bearing 2,5-furandicarboxylic moieties

Cited by 13 publications

References 42 publications

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

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

Highly Flexible Poly(1,12-dodecylene 5,5′-isopropylidene-bis(ethyl 2-furoate)): A Promising Biobased Polyester Derived from a Renewable Cost-Effective Bisfuranic Precursor and a Long-Chain Aliphatic Spacer

Recent Progress on Bio-Based Polyesters Derived from 2,5-Furandicarbonxylic Acid (FDCA)

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