A green strategy for the synthesis of poly(ethylene succinate) and its copolyesters via enzymatic ring opening polymerization

Morales‐Huerta, Juan Carlos; Ilarduya, Antxon Martı́nez de; Muñoz‐Guerra, Sebastián

doi:10.1016/j.eurpolymj.2017.08.043

Cited by 17 publications

(11 citation statements)

References 26 publications

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“…Cyclic oligomers of butylene succinate and ethylene succinate, c (BS) n and c (ES) n respectively, were prepared by the high-dilution condensation (HDC) method [ 28 ] following the experimental procedures reported by us [ 14 , 29 ]. Cyclic oligo[di- O -2-(hydroxyethyl) resorcinol 2,5-furandicarboxylate]s, abbreviated as c (RF) n , were synthesized from HER and 2,5-furandicarboxylic dichloride (FDCA-Cl 2 ) by applying the HDC methodology in a manner as we reportedfor the synthesisof cyclic oligo(butylene 2,5-furandicarboxylate)s with some minor modifications [ 30 ].…”

Section: Methodsmentioning

confidence: 99%

Modulating the Tg of Poly(alkylene succinate)s by Inserting Bio-Based Aromatic Units via Ring-Opening Copolymerization

2017

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Abstract:Two series of aliphatic-aromatic copolyesters derived from succinic and 2,5-furandicarboxylic acids, and di-O-2-(hydroxyethyl) resorcinol as diol substituent of either 1,4-butanediol or ethylene glycol, respectively, were obtained by ring opening polymerization(ROP) performed in bulk and catalyzed by Sn(Oct) 2 . Cyclic oligomers of furandicarboxylate of di-O-2-(hydroxyethyl) resorcinol were successfully synthesized by high-dilution condensation, and then copolymerized with cyclic oligomers of either butylene or ethylene succinate. The synthesized resorcinol-containing succinate-furanoatecopolyesters had M w oscillating between 50,000 and 30,000 g·mol −1 depending on composition, and they all displayed a nearly random microstructure. They showed an excellent thermal stability with onset decomposition temperatures near 300 • C. They are amorphous with T g increasing monotonically with the content in resorcinol in both series with values ranging from −30 or −13 • C for butylene and ethylene-based copolyesters, respectively, up to around 45 • C. The resorcinol-containing succinate-furanoate copolyesters showed appreciable hydrolytic degradation when incubated for a few weeks in water under physiological conditions, a behavior that was notably enhanced in the presence of lipases.

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Section: Methodsmentioning

confidence: 99%

Modulating the Tg of Poly(alkylene succinate)s by Inserting Bio-Based Aromatic Units via Ring-Opening Copolymerization

2017

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“…Recently, Muñoz‐Guerra's group [ 151 ] obtained poly(ethylene succinate) (PES) by enzymatic ring opening polymerization of cyclic oligo(ethylene succinate)s, which were prepared by CALB‐catalyzed cyclocondensation of dimethyl succinate (DMS) and ethylene glycol. Polyesters presented high M w above 60 000 g mol −1 .…”

Section: Polyesters Synthesized By Enzymatic Polymerizationmentioning

confidence: 99%

“…These copolyesters were able to crystallize in the entire composition range and displayed a pseudoeutectic region. [ 151,153–155 ]…”

Section: Polyesters Synthesized By Enzymatic Polymerizationmentioning

confidence: 99%

Enzymatic Synthesis of Polyesters and Their Bioapplications: Recent Advances and Perspectives

Hevilla

Sonseca

Echeverría

et al. 2021

Macromolecular Bioscience

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This article reviews the most important advances in the enzymatic synthesis of polyesters. In first place, the different processes of polyester enzymatic synthesis, i.e., polycondensation, ring opening, and chemoenzymatic polymerizations, and the key parameters affecting these reactions, such as enzyme, concentration, solvent, or temperature, are analyzed. Then, the latest articles on the preparation of polyesters either by direct synthesis or via modification are commented. Finally, the main bioapplications of enzymatically obtained polyesters, i.e., antimicrobial, drug delivery, or tissue engineering, are described. It is intended to point out the great advantages that enzymatic polymerization present to obtain polymers and the disadvantages found to develop applied materials.

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“…PES is a material with outstanding biodegradable property that makes it an excellent candidate for preparation of biodegradable polymers . Unfortunately, the application field of PES in industry was greatly limited because of their high cost and poor physical and mechanical properties . On the other hand, PET possesses excellent physical and mechanical properties and low cost compared with PES, but lack of biodegradability.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and nonisothermal crystallization kinetics of biodegradable poly(ethylene terephthalate‐co‐ethylene succinate)s

Guan

Zhan

et al. 2019

J of Applied Polymer Sci

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In the current work, a series of biodegradable poly(ethylene terephthalate-co-ethylene succinate)s (P[ET-co-ES]s) were prepared via a traditional melting polycondensation method. First of all, the structures of prepared copolymers were characterized by nuclear magnetic resonance and Fourier transform infrared measurements. Meanwhile, the thermal properties of prepared samples were analyzed by differential scanning calorimetry and thermogravimetric analysis measurements, respectively. Subsequently, the mechanical properties of the P(ET-co-ES)s were evaluated, the tensile strength of P(ET-co-ES)s decreased with increasing of PES content in copolymer, however, corresponding P(ET-co-ES)s exhibited better elongation at break. Next, the biodegradability of P(ET-co-ES)s was evaluated using lipase as degrading enzyme. The results presented that the biodegradability of P(ET-co-ES)s improved with PES content, the corresponding results were supported by scanning electron microscopy test. Finally, the Mo's modified Avrami equation was employed to analyze the nonisothermal crystallization kinetics of prepared copolymers. The results showed the addition of the PES component improved the crystallization properties of the prepared P(ET-co-ES)s.

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A green strategy for the synthesis of poly(ethylene succinate) and its copolyesters via enzymatic ring opening polymerization

Cited by 17 publications

References 26 publications

Modulating the Tg of Poly(alkylene succinate)s by Inserting Bio-Based Aromatic Units via Ring-Opening Copolymerization

Modulating the Tg of Poly(alkylene succinate)s by Inserting Bio-Based Aromatic Units via Ring-Opening Copolymerization

Enzymatic Synthesis of Polyesters and Their Bioapplications: Recent Advances and Perspectives

Synthesis and nonisothermal crystallization kinetics of biodegradable poly(ethylene terephthalate‐co‐ethylene succinate)s

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