Poly(1,20-eicosanediyl 2,5-furandicarboxylate), a biodegradable polyester from renewable resources

Soares, M.J.; Dannecker, Patrick‐Kurt; Vilela, Carla; Bastos, José Mesquita; Meier, Michael A. R.; Sousa, Andreia F.

doi:10.1016/j.eurpolymj.2017.03.023

Cited by 47 publications

(34 citation statements)

References 52 publications

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“…In the first step, the (co)polyesters were prepared by a conventional bulk polyesterification approach [18,41]. These (co)polyesters spanned from the neat PBF to neat PBDG, and encompassed their copolyesters with different relative furanoate/digycolate amounts (90/10, 75/25, and the never reported 50/50, 25/75, and 10/90 mol %).…”

Section: Resultsmentioning

confidence: 99%

“…This behaviour was due to the initial re-orientation of the functional groups at surface of the films, allowing the water drops to spread more easily [45]. Among different nanocomposites, the CA water , after 15 s, increased with the increasing furanoate content in the copolyester (from 45 to 100°), mostly due to the hydrophobic character of the furanoate-based polyesters [41]. The Ac-BC film showed an intermediate CA water of approximately 67.9° after 15 s, in accordance with nanofibre affinity to the polyesters, and consequently good dispersion in the thermoplastic matrices, especially PBF- co -PBDG-50/50 to -10/90, and PBDG.…”

Section: Resultsmentioning

confidence: 99%

“…The polyesters were synthesized via a procedure described elsewhere [18,41]: Fisher esterification of FDCA, esterification, and finally polycondensation reaction. In brief, dimethyl 2,5-dimethylfurandicarboxylate (DMFDC) was first prepared by reacting FDCA (192.2 mmol) with an excess of methanol (364 mL), under acidic conditions (HCl, 15 mL), at 80 °C for 15 h. The reaction mixture was allowed to cool down, and the ensuing white precipitate was isolated by filtration in 70% yield.…”

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Furanoate-Based Nanocomposites: A Case Study Using Poly(Butylene 2,5-Furanoate) and Poly(Butylene 2,5-Furanoate)-co-(Butylene Diglycolate) and Bacterial Cellulose

et al. 2018

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Polyesters made from 2,5-furandicarboxylic acid (FDCA) have been in the spotlight due to their renewable origins, together with the promising thermal, mechanical, and/or barrier properties. Following the same trend, (nano)composite materials based on FDCA could also generate similar interest, especially because novel materials with enhanced or refined properties could be obtained. This paper presents a case study on the use of furanoate-based polyesters and bacterial cellulose to prepare nanocomposites, namely acetylated bacterial cellulose/poly(butylene 2,5-furandicarboxylate) and acetylated bacterial cellulose/poly(butylene 2,5-furandicarboxylate)-co-(butylene diglycolate)s. The balance between flexibility, prompted by the furanoate-diglycolate polymeric matrix; and the high strength prompted by the bacterial cellulose fibres, enabled the preparation of a wide range of new nanocomposite materials. The new nanocomposites had a glass transition between −25-46 • C and a melting temperature of 61-174 • C; and they were thermally stable up to 239-324 • C. Furthermore, these materials were highly reinforced materials with an enhanced Young's modulus (up to 1239 MPa) compared to their neat copolyester counterparts. This was associated with both the reinforcing action of the cellulose fibres and the degree of crystallinity of the nanocomposites. In terms of elongation at break, the nanocomposites prepared from copolyesters with higher amounts of diglycolate moieties displayed higher elongations due to the soft nature of these segments.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Furanoate-Based Nanocomposites: A Case Study Using Poly(Butylene 2,5-Furanoate) and Poly(Butylene 2,5-Furanoate)-co-(Butylene Diglycolate) and Bacterial Cellulose

et al. 2018

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“…Some examples of polyesters synthesized from FDCA are poly(ethylene 2,5-furandicarboxylate) (PEF) [3] and poly(1,4-butylene 2,5-furandicarboxylate) (PBF), among others, with similar properties to those of their TPA counterparts [4,5,6,7,8,9,10,11] or even enhanced properties such as for example barrier properties or degradability under enzymatic conditions [12,13]. Furthermore, several other diols besides linear ones have been explored to prepare FDCA-based homopolymers, namely branched diols such as 1,2-propanediol, 2,3-butanediol, 2-methyl-1,3-propanediol and 2,2-dimethyl-1,3-propanediol [14,15,16,17,18,19,20].…”

Section: Introductionmentioning

confidence: 99%

Co-Polymers based on Poly(1,4-butylene 2,5-furandicarboxylate) and Poly(propylene oxide) with Tuneable Thermal Properties: Synthesis and Characterization

et al. 2019

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Poly(ether ester)s (PEEs) represent a promising class of segmented co-polymers, nevertheless the synthesis of PEEs based on renewable 2,5-furandicarboxylic acid (FDCA) is still scarce. In this context, a series of poly(1,4-butylene 2,5-furandicarboxylate)-co-poly(poly(propylene oxide) 2,5-furandicarboxylate) co-polyesters with different composition of stiff poly(1,4-butylene 2,5-furandicarboxylate) (PBF) and soft poly(poly(propylene oxide) 2,5-furandicarboxylate) (PPOF) moieties were synthesized, via a two-step bulk polytransesterification reaction. The molar ratio of PBF/PPOF incorporated was varied (10 to 50 mol%) in order to prepare several novel materials with tuned properties. The materials were characterised in detail through several techniques, namely ATR FTIR, 1H and 13C NMR, TGA, DSC, DMTA and XRD. Their hydrolytic and enzymatic degradation evaluation was also assessed. These new co-polymers showed either a semi-crystalline nature when higher PBF/PPOF ratios were used, and for approximately equal amounts of PBF and PPOF an amorphous co-polyester was obtained instead.

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“…The Bikiaris group showed that adipate-based co-polymers have enhanced degradability, reaching near 100% weight loss in only 20 days (Papadopoulos et al, 2018 ); although more moderate degradability was reported for copolymers from succinic acid (Terzopoulou et al, 2016 ). Clearly, these copolymers' enzymatic hydrolysis positively depended on the engineered comonomers ratio and on the related flexible polymer structure of the aliphatic moieties (Soares et al, 2017 ), as well as on the decrease of crystallinity (Papadopoulos et al, 2018 ).…”

Section: Pef End-of-lifementioning

confidence: 99%

A Perspective on PEF Synthesis, Properties, and End-Life

et al. 2020

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This critical review considers the extensive research and development dedicated, in the last years, to a single polymer, the poly(ethylene 2,5-furandicarboxylate), usually simply referred to as PEF. PEF importance stems from the fact that it is based on renewable resources, typically prepared from C6 sugars present in biomass feedstocks, for its resemblance to the high-performance poly(ethylene terephthalate) (PET) and in terms of barrier properties even outperforming PET. For the first time synthesis, properties, and end-life targeting-a more sustainable PEF-are critically reviewed. The emphasis is placed on how synthetic roots to PEF evolved toward the development of greener processes based on ring open polymerization, enzymatic synthesis, or the use of ionic liquids; together with a broader perspective on PEF end-life, highlighting recycling and (bio)degradation solutions.

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Poly(1,20-eicosanediyl 2,5-furandicarboxylate), a biodegradable polyester from renewable resources

Cited by 47 publications

References 52 publications

Furanoate-Based Nanocomposites: A Case Study Using Poly(Butylene 2,5-Furanoate) and Poly(Butylene 2,5-Furanoate)-co-(Butylene Diglycolate) and Bacterial Cellulose

Furanoate-Based Nanocomposites: A Case Study Using Poly(Butylene 2,5-Furanoate) and Poly(Butylene 2,5-Furanoate)-co-(Butylene Diglycolate) and Bacterial Cellulose

Co-Polymers based on Poly(1,4-butylene 2,5-furandicarboxylate) and Poly(propylene oxide) with Tuneable Thermal Properties: Synthesis and Characterization

A Perspective on PEF Synthesis, Properties, and End-Life

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