A New Generation of Furanic Copolyesters with Enhanced Degradability: Poly(ethylene 2,5‐furandicarboxylate)‐<i>co</i>‐poly(lactic acid) Copolyesters

Matos, Marina; Sousa, Andreia F.; Fonseca, A. C.; Freire, Carmen S.R.; Coelho, Jorge F. J.; Silvestre, Armando J. D.

doi:10.1002/macp.201400175

Cited by 101 publications

(86 citation statements)

References 32 publications

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“…These biobased comonomers have been used essentially to tackle the lack of biodegradability of PEF and PBF (and certainly many others), and, hence, foresees a rapid expansion for this new generation of furan-derived copolyesters. Promising poly(ethylene 2,5-furandicarboxylate)-co-poly(lactic acid) (PEF-co-PLA) copolyesters were developed by Sousa et al, 41 copolymerising BHEFDC and PLA (with M n around 5,000 g mol -1 ), using Sb 2 O 3 or SnCl 2 .2H 2 O as catalyst (Scheme 4).…”

Section: Poly(25-furan Dicarboxylate)s Incorporating Lactic Succinimentioning

confidence: 99%

Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: a tribute to furan excellency

et al. 2015

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Motivated by a general concern on sustainability and environmental issues, a sparkling search for renewable-based polymers has grown exponentially in recent years. This search definitely spotlighted polyesters derived from 2,5-furandicarboxylic acid, among other polymers, as some of the most promising, especially due to the resemblance of this renewable monomer to the well-known petroleum-based terephthalic acid, as well as for the possibility of preparing innovative materials. The huge number of recent papers and patents about this family of polymers explore aspects such diverse as synthesis with other renewable-based monomers, leading to the preparation of materials with enhanced thermo-mechanical, biodegradability and liquid crystalline properties, among other features. Additional aspects pursued in such studies are innovation in the synthetic approaches or its optimisation; and also the development of applications for everyday-life objects like for example packaging materials, especially bottles, textiles, coating, toners, among many other uses. Despite this intense activity little has been reviewed recently about this unique family of polyesters, or derived polymers, as the only reviews on the subject date-back from the last century. In this perspective, the present appraisal aims at contributing to fulfil this literature gap, covering recent aspects related with challenges of developing polyesters, polyamides, or other polymers from 2,5-furandicarboxylic acid and their precursors. Emphasis is placed on monomer synthesis, polymerisation reactions, catalysts and applications.A tribute to 2,5-furandicarboxylic acid excellency and the myriad of novel polyesters, but also polyamides, among other polycondensates, is comprehensively done.

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Section: Poly(25-furan Dicarboxylate)s Incorporating Lactic Succinimentioning

confidence: 99%

Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: a tribute to furan excellency

et al. 2015

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“…The signals at 4.52 ppm (c) and 4.34 ppm (d) are also observed. These two peaks are related to [25], which is associated with the proportion of each integration area of methylene proton attached to ester groups (δ ≈ 4.58, 4.52, 4.34 and 4.28 ppm respectively) of all diads, viz., F-B, F-CL, CL-B, and CL-CL (Table 2). In all PBFCL, sequence length of both hard (BF segments) and soft segments (CL segments) are short, indicated by large proportion of F-CL and CL-B diads.…”

Section: Characterizationmentioning

confidence: 99%

Poly(butylene 2,5-furandicarboxylate-ε-caprolactone): A new bio-based elastomer with high strength and biodegradability

Zheng¹,

Zang²,

Wang³

et al. 2017

Express Polym. Lett.

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Abstract.A new bio-based elastomer, poly(butylene 2,5-furandicarboxylate-ε-caprolactone) (PBFCL), has been synthesized from 2,5-furandicarboxylic acid, 1,4-butanediol, and ε-caprolactone successfully for the first time. The obtained copolyester was characterized in terms of chemical structure, thermal and mechanical properties, and enzymatic degradability. In PBFCL elastomer, butylene-2,5-furandiacrboxylate units (hard segments) crystallize to serve as physical crosslinks while ε-caprolactone polyester diol (soft segments) provide flexibility. PBFCL is a multi-blocked copolyester with randomly distributed rigid and soft segments. It possesses original feature of high strength and biodegradability stemming from the uses of aromatic and aliphatic monomers respectively. An important aspect of this new furanic-aliphatic polyester is its tailor-made properties simply achieved by changing the content of hard or soft segments. Typically, PBFCL-40 of optimal composition has Young's modulus as low as 15.4 MPa, tensile strength as high 24.8 MPa, and elongation as long as 885%.

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“…Similar results were obtained in our previous work with aliphatic-aromatic copolymers 61 , as also by other researchers 82,85 . In the case of furanoate copolymers it was found that copolymerization of PEF with lactic acid enhanced its hydrolysis rate 86,87 , as also the presence of butylene adipate in poly(butylene furanoate) polyester resulted in accelerated hydrolysis by lipase 88 . This behavior is attributed to the higher hydrophobicity of the furanoate units and the increased rigidity they provide, therefore less mobility of the macromolecular chains.…”

Section: Enzymatic Hydrolysismentioning

confidence: 99%

Biobased poly(ethylene furanoate-co-ethylene succinate) copolyesters: solid state structure, melting point depression and biodegradability

et al. 2016

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Poly(ethylene furanoate) (PEF) is a fully bio-based polyester with unique gas barrier properties, considered an alternative to poly(ethylene terephthalate) (PET) in food packaging applications. However, it is not biodegradable. For this reason copolymerization with the aliphatic succinic acid monomer, was followed. The respective poly(ethylene furanoate-co-ethylene succinate) (PEFSu) copolymers were prepared via melt polycondensation from 2,5-dimethylfuran-dicarboxylate, succinic acid and ethylene glycol at different ratios.1 HNMR spectroscopy showed the copolymers are random. The crystallization and melting of the copolymers were thoroughly evaluated. Isodimorphic cocrystallization was concluded from both the 2 WAXD patterns and the minimum in the plots of melting temperature versus composition. The pseudo-eutectic melting point corresponded to an ethylene succinate content of about 30 mol%. The enzymatic hydrolysis tests using of Rhizopus delemarand Pseudomonas Cepacia lipase, revealed that the copolymers with up to 50 mol% ES units show measurable weight loss rates. For higher ES content, the copolymers showed fast hydrolysis.

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A New Generation of Furanic Copolyesters with Enhanced Degradability: Poly(ethylene 2,5‐furandicarboxylate)‐co‐poly(lactic acid) Copolyesters

Cited by 101 publications

References 32 publications

Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: a tribute to furan excellency

Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: a tribute to furan excellency

Poly(butylene 2,5-furandicarboxylate-ε-caprolactone): A new bio-based elastomer with high strength and biodegradability

Biobased poly(ethylene furanoate-co-ethylene succinate) copolyesters: solid state structure, melting point depression and biodegradability

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