Thermal degradation behavior of poly[(R)-3-hydroxybutyrate-co-4-hydroxybutyrate]

Omura, Taku; Goto, Tatsuya; Maehara, Akira; Kimura, Satoshi; Abe, Hideki; Iwata, Tadahisa

doi:10.1016/j.polymdegradstab.2020.109460

Cited by 15 publications

(12 citation statements)

References 39 publications

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“…The reaction rate constant k was calculated using Nishida’s method, and the Arrhenius plot was obtained considering ln k and 1/ T (Figure S4). The activation energy E a was calculated as 100.5 kJ/mol, which is close to the reported E a values for P(3HB) (122.5 kJ/mol), P(3HB- co -5.5 mol %-3HHx) (90.6 kJ/mol) and P(3HB- co -16 mol %-4HB) (127.0 kJ/mol) . Therefore, the thermal stability of P(3HB- co -16 mol %-4HB) was nearly identical to that of the P(3HB) homopolymer and P(3HB- co -5.5 mol %-3HHx).…”

Section: Resultssupporting

confidence: 86%

Elastic Marine Biodegradable Fibers Produced from Poly[(R)-3-hydroxybutylate-co-4-hydroxybutylate] and Evaluation of Their Biodegradability

Omura

Komiyama

Maehara

et al. 2021

ACS Appl. Polym. Mater.

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Marine biodegradable fibers with high strength and elasticity were successfully fabricated from microbial polyesters using a melt-spinning method. Polymers were melted at temperatures lower than the constituent melting temperatures, and the obtained fibers were stretched at room temperature. The molecular weights of the fibers processed by this melt-spinning method remained unchanged, suggesting that the developed approach is very effective for polyhydroxyalkanoates, which typically exhibit low thermal stability during the melting process. The obtained fibers had tensile strengths >200 MPa and elongation at break of ∼200%, making them comparable to nonbiodegradable elastic fibers processed from polyethylene and polypropylene. It was confirmed that these fibers were completely degraded by both seawater from Tokyo Bay and freshwater from Sanshiro Pond after less than 1 month. Interestingly, periodically stacked lamellar structures of 200 nm that comprised at least 30 lamellae were generated following the biodegradation of the amorphous region of the fiber surface.

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Section: Resultssupporting

confidence: 86%

Elastic Marine Biodegradable Fibers Produced from Poly[(R)-3-hydroxybutylate-co-4-hydroxybutylate] and Evaluation of Their Biodegradability

Omura

Komiyama

Maehara

et al. 2021

ACS Appl. Polym. Mater.

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“…These results suggest that the major thermal degradation behavior of the resorcinol‐based semiaromatic polyesters was the cleavage of the ester bond. As the pathways for cleavage of the ester bond, free‐radical scission and elimination of the α ‐hydrogen for the ester bond were considered [ 29,44–46 ] ( Scheme ). The anion or radical generated under pyrolysis and a lone pair of oxygen in the carbonyl group work as a hydrogen acceptor for the α ‐hydrogen elimination.…”

Section: Resultsmentioning

confidence: 99%

Substituent Effects on Thermal and Mechanical Properties of Resorcinol‐Based Semiaromatic Polyesters

Goto

Abe

2022

Macro Chemistry & Physics

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Recently biobased plastics draw attention as eco‐friendly materials, and it is important to study the effects of substituents, which are popularly found in natural products, on the characteristics of the resulted polymers. In this study, twelve resorcinol‐based semiaromatic polyesters are successfully synthesized using four types of resorcinol derivatives (resorcinol, 2‐methylresorcinol, 5‐methylresorcinol, and 2,5‐dimethylresorcinol) and three types of dicarboxylic acids (glutaric acid, adipic acid, and pimelic acid) to investigate the effect of methylation at the 2‐ and 5‐positions in resorcinol. Glass‐transition temperature of the polyesters is located from ‐3.1 to 37.9 °C, and rises with increasing the number of methyl groups in a resorcinol unit. Crystallinity of the polyesters decreases by methylation to a resorcinol unit, except the polyester from 2‐methylresorcinol and pimelic acid. The mechanical properties of the solvent‐cast films for the polyesters are tunable by the site and number of methyl groups in a resorcinol unit. The major thermal degradation of the polyesters is observed above 300 °C, and the minor thermal decomposition appears between 100 and 200 °C for the polyesters without the resorcinol methylated at the 2‐position and pimelic acid unit.

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“…3b), followed by conversion to CA. 8 After successful thermal depolymerization of PHB to CA in [EMIM][AcO] IL had been confirmed at 120 °C, the same process was studied at reaction temperatures 80, 100, and 140 °C with the PHB loading kept at 20 wt%. The 1 H NMR spectra in Fig.…”

Section: Methodsmentioning

confidence: 99%

“…Recently, Iwata et al also proposed a similar depolymerization mechanism for the thermal conversion of poly (3-hydroxybutyrate- co -4-hydroxybutyrate), PHB-copolymer, where the formation of cis - and trans -CA, 3-butenoic acid, and γ-valerolactone, as well as low molecular weight dimers and trimers, proceeds through the unzipping β-elimination route. 8 Samori et al synthesized CA from pure PHB as well as PHB-rich bacteria, whereby 92% selectivity for CA was achieved in the mixture of products after thermal distillation. 5 c Additionally, Ariffin et al reported both catalytic and non-catalytic thermal conversion of PHB-homo-polymer in separate studies, where the formation of CA proceeds through repetitive β-elimination in both processes.…”

Section: Introductionmentioning

confidence: 99%

Sustainable, highly selective, and metal-free thermal depolymerization of poly-(3-hydroxybutyrate) to crotonic acid in recoverable ionic liquids

et al. 2022

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Thermal degradation behavior of poly[(R)-3-hydroxybutyrate-co-4-hydroxybutyrate]

Cited by 15 publications

References 39 publications

Elastic Marine Biodegradable Fibers Produced from Poly[(R)-3-hydroxybutylate-co-4-hydroxybutylate] and Evaluation of Their Biodegradability

Elastic Marine Biodegradable Fibers Produced from Poly[(R)-3-hydroxybutylate-co-4-hydroxybutylate] and Evaluation of Their Biodegradability

Substituent Effects on Thermal and Mechanical Properties of Resorcinol‐Based Semiaromatic Polyesters

Sustainable, highly selective, and metal-free thermal depolymerization of poly-(3-hydroxybutyrate) to crotonic acid in recoverable ionic liquids

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