Chemically recyclable bio-based polyester composed of bifuran and glycerol acetal

Hayashi, Senri; Tachibana, Yuya; Tabata, Naoto; Kasuya, Kazuhiko

doi:10.1016/j.eurpolymj.2020.110242

Cited by 13 publications

(12 citation statements)

References 31 publications

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“…Acetalization of bis-furfural with glycerol results in three isomeric diols, which can be polycondensed with either succinic or phthalic acid to provide chemically recyclable materials with enhanced thermal properties. 186 Since the C2 and C5 positions of the furan ring are susceptible to electrophilic attack, furoic acid methyl ester was condensed with levulinic acid to provide a bis-furanic diester monomer, which was then used for the synthesis of polyamides with different diamines. 187 Additionally, a partially biorenewable amine obtained by the condensation of furfurylamine (FA) with acetone was used for this purpose.…”

Section: Scattered Materialsmentioning

confidence: 99%

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Recent advances in the development of green furan ring-containing polymeric materials based on renewable plant biomass

Karlinskii

Ananikov

2023

Chem. Soc. Rev.

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Section: Scattered Materialsmentioning

confidence: 99%

Section: Linear Typementioning

confidence: 99%

Recent advances in the development of green furan ring-containing polymeric materials based on renewable plant biomass

Karlinskii

Ananikov

2023

Chem. Soc. Rev.

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“…21 Acetals and ketals are generally stable under basic conditions but are susceptible to hydrolytic degradation via acidic hydrolysis. 22 However, such an inherent instability can open a pathway for chemical recycling of acetal-containing polymers, 20,23 or promote biodegradation as recently reported by Zhang and Zhu. 24 The latter study demonstrated that the ester bond in spirodiacetal-containing polyesters can be enzymatically hydrolyzed after degradation of the diacetal functionality in a 2 M aqueous HCl solution.…”

Section: Introductionmentioning

confidence: 93%

“…Recently, a bifurane-based glycerol diacetal was reported by Kasuya et al, 20 and mannitol-based diketals with camphor have been disclosed by Suh's research group. 21 Acetals and ketals are generally stable under basic conditions but are susceptible to hydrolytic degradation via acidic hydrolysis.…”

Section: Introductionmentioning

confidence: 99%

“…For example, Du Prez et al used 1,4-cyclohexadienone and 4,4′-dicyclohexanone, and Suh et al employed camphorquinone, to prepare the corresponding glycerol diketals. Recently, a bifurane-based glycerol diacetal was reported by Kasuya et al, and mannitol-based diketals with camphor have been disclosed by Suh’s research group . Acetals and ketals are generally stable under basic conditions but are susceptible to hydrolytic degradation via acidic hydrolysis .…”

Section: Introductionmentioning

confidence: 99%

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Chemically Recyclable Poly(β-thioether ester)s Based on Rigid Spirocyclic Ketal Diols Derived from Citric Acid

et al. 2022

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Incorporating rigid cyclic acetal and ketal units into polymer structures is an important strategy toward recyclable high-performance materials from renewable resources. In the present work, citric acid, a widely used platform chemical derived from biomass, has been efficiently converted into di- and tricyclic diketones. Ketalization with glycerol or trimethylolpropane afforded rigid spirodiols, which were obtained as complex mixtures of isomers. After a comprehensive NMR analysis, the spirodiols were converted into the respective di(meth)acrylates and utilized in thiol–ene polymerizations in combination with different dithiols. The resulting poly(β-thioether ester ketal)s were thermally stable up to 300 °C and showed glass-transition temperatures in a range of −7 to 40 °C, depending on monomer composition. The polymers were stable in aqueous acids and bases, but in a mixture of 1 M aqueous HCl and acetone, the ketal functional groups were cleanly hydrolyzed, opening the pathway for potential chemical recycling of these materials. We envision that these novel bioderived spirodiols have a great potential to become valuable and versatile bio-based building blocks for several different kinds of polymer materials.

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A Multifunctional Bio‐Based Polyester Material Integrated with High Mechanical Performance, Gas Barrier Performance, and Chemically Closed‐Loop

Li,

Wu,

et al. 2024

Adv Funct Materials

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The development of multifunctional bio‐based materials with closed‐loop chemically recyclable plastics can be a paramount response to the worldwide plastic waste predicament. However, the trade‐off dilemma between the high performance and easy recycling performance of these materials still encounters huge challenges. In this contribution, inspired by the significant contribution of the hydrogen bonding networks to enhanced mechanical and gas barrier performance as well as the cosolvents to enhance recycling performance, a novel polyester material (PBHyF) synthesized by bio‐based monomers that integrate high‐performance and efficient chemical closed‐loop is presented. PBHyF show ultra‐high mechanical properties (83.2 MPa, 233.9%) and barrier properties (CO2 0.0157 barrer, O2 0.0071 barrer, H2O 5.518E‐15 g·cm/cm2·s·Pa) that are greater than bio‐based materials and most engineering plastics of previous work. More significantly, PBHyF also exhibits multifunctionality with excellent ultraviolet shielding properties, solvent‐resistant properties, and easy recycling performance. The initial monomers of PBHyF can be obtained in exceptional yields (>90.0%) and purity (>99.0%) under mild conditions by a simple energy‐efficient rapid chemical‐solvolysis strategy, even with polyolefin blend plastics. Further possesses similar high‐performance repolymerized polyester comparable to the polyester before recycling. Hence, these state‐of‐art high‐performance and easy‐recycling bio‐based materials provide a new approach for a green, sustainable material economy.

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Chemically recyclable bio-based polyester composed of bifuran and glycerol acetal

Cited by 13 publications

References 31 publications

Recent advances in the development of green furan ring-containing polymeric materials based on renewable plant biomass

Recent advances in the development of green furan ring-containing polymeric materials based on renewable plant biomass

Chemically Recyclable Poly(β-thioether ester)s Based on Rigid Spirocyclic Ketal Diols Derived from Citric Acid

A Multifunctional Bio‐Based Polyester Material Integrated with High Mechanical Performance, Gas Barrier Performance, and Chemically Closed‐Loop

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