Biodegradability of polyesters comprising a bio-based monomer derived from furfural

Tachibana, Yuya; Yamahata, Masayuki; Ichihara, Hirofumi; Kasuya, Ken-ichi

doi:10.1016/j.polymdegradstab.2017.10.001

Cited by 25 publications

(20 citation statements)

References 60 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The resultant POBCs were amorphous polyesters with transparency and flexibility, because the bulky OBCA unit could not form a crystalline phase. Furthermore, the POBCs have environmental biodegradability, which is a valuable property from the perspective of sustainability. , POBCs can potentially replace general-purpose plastics, even though their physical properties like strength and thermal properties are still lacking on various occasions.…”

Section: Introductionmentioning

confidence: 99%

“…For example, the physical properties of poly(butylene succinate- co -butylene adipate) (PBSA, the copolymer of PBS with poly(butylene adipate) (PBA), which disturbs the crystallinity of PBS) depend on the ratio of PBS and PBA units. The copolymerization with cyclic acetalized sugars, which depressed the crystallizability of PBS, provided flexibility and higher glass transition temperature. , The copolymerization with PEF as a rigid unit provided further strength to PBS. , Because BD, SA, and OBCA are potentially biobased building blocks produced from furfural alone and poly(butylene oxabicyclate) (PBO) produced from BD and OBCA has the best physical properties and biodegradability among POBCs, we designed a copolymer between PBS and PBO as a new biobased material. PBS is a crystalline polymer and PBO is an amorphous polymer composed of a bulky oxabicyclate unit, so the introduction of butylene oxabicyclate (BO) unit to butylene succinate (BS) unit would disturb the crystalline phase of PBS and provide flexibility to PBS.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis, Physical Properties, and Biodegradability of Biobased Poly(butylene succinate-co-butylene oxabicyclate)

Tachibana

Yamahata

Kimura

et al. 2018

ACS Sustainable Chem. Eng.

Self Cite

View full text Add to dashboard Cite

Furfural, a compound easily manufactured from hemicellulose on the global scale, has gained attention as a second-generation biomass resource. The synthesis of oxabicyclodicarboxylic anhydride (OBCA) from furfural alone and its polymerization with diol to form the biobased and biodegradable polyoxabicyclate (POBC) make OBCA a novel biobased monomer building block. To control the physical properties of POBC, we synthesized a copolyester of butanediol (BD), succinic anhydride (SAh), and OBCA. The structures of the resultant poly(butylene succinate-co-butylene oxabicyclate) (P(BS-co-BO)) polymers were studied using 1H and 13C NMR spectrometry, size-exclusion chromatography, thermal gravimetric analysis, differential scanning calorimetry, and wide-angle X-ray diffraction analysis. Physical properties of the melt-pressed films were examined by tensile strength testing, and the hydrolyzability of P(BS-co-BO)s was evaluated using a clear zone formation method with bacteria. To examine the environmental biodegradability of P(BS-co-BO), the biochemical oxygen demand for degrading their constituents was measured using the mixed inoculum method.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, Physical Properties, and Biodegradability of Biobased Poly(butylene succinate-co-butylene oxabicyclate)

Tachibana

Yamahata

Kimura

et al. 2018

ACS Sustainable Chem. Eng.

Self Cite

View full text Add to dashboard Cite

show abstract

“…However, the ROP route for generating nonanhydride-derived aromatic polyesters is almost inaccessible. An alternative synthesis route of linear biopolyesters with cyclic units is the melt polymerization (MP) of bio-based anhydrides with diols, and diverse desired building blocks can also be introduced to obtain renewable copolyesters with overall enhanced properties. − Furthermore, streaming the conversion of biomass to linear polyesters with oxabicyclic units via MP with a continuous flow process has been proposed to have potential industrial prospects . However, the unsatisfactory yields and the low molecular weight result in disappointing T g values and mechanical strength of linear polyesters with oxabicyclic units, often due to the readily volatilizable anhydrides during the MP process.…”

Section: Introductionmentioning

confidence: 99%

Development of High-Molecular-Weight Fully Renewable Biopolyesters Based on Oxabicyclic Diacid and 2,5-Furandicarboxylic Acid: Promising as Packaging and Medical Materials

Zhang

Jiang

et al. 2021

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

Renewable and biodegradable linear polyesters with oxabicyclic units based on the ring-opening polymerization (ROP) have attracted considerable interest as alternatives to petrochemical-based polyesters. However, incorporating bio-based aromatic building blocks into the linear polyesters with oxabicyclic units by the ROP process is limited. Herein, we report three series of oxabicyclic renewable polyesters based on oxabicyclic diacid (OBDA), monomethyl oxabicyclic diacid (MBDA), and oxabicyclic anhydride with dimethyl substituents (d-MBDA) derived from bio-based furanics and synthesized via melt polymerization (MP). The molecular weights of the polyesters obtained from OBDA were significantly higher than those of the reported polyesters based on OBDA anhydride derivatives, leading to significantly higher glass-transition temperature (T g ) values and tensile strength. Furthermore, a series of fully bio-based copolyesters (PBOB m F n ) was first obtained via the MP strategy by the incremental replacement of OBDA with bio-based 2,5-furandicarboxylic acid (FDCA). The incorporation of FDCA units significantly improved the thermal stabilities and mechanical properties of the linear polyesters with oxabicyclic units and endowed them with gas barrier properties that were better than those of commercial poly(ethylene terephthalate) (PET). The T g values of PBOB m F n ranged from 38.8 to 40.8 °C and were comparable with that of the commercial biomedical material Vicryl. Additionally, the trade-off between OBDA and FDCA units can control the fast biodegradation and environmental durability of the PBOB m F n polyester series. PBOB m F n also showed excellent biocompatibility to and was safe for both RAW264.7 and PC12 cells. The strategy of the incorporation of FDCA building blocks via MP enhanced the comprehensive properties of the linear polyesters with oxabicyclic units; moreover, the adjustment between FDCA and OBDA units can be leveraged to control the polyester roles between packaging and biomedical fields while retaining the completely renewable nature of the parent of polyesters.

show abstract

“…However, the contribution of renewable polymeric materials to the total volume of polymers produced is negligible . Degradability is another material requirement for sustainable future and majority of the polymers produced today do not degrade over extended (100s of years) period of time . Thus, increasing consumption coupled with meagre degradation has led to accumulation of alarming volumes of polymers and has turned the planet into plastic soup .…”

Section: Introductionmentioning

confidence: 99%

Cross‐metathesis of biorenewable dioxalates and diols to film‐forming degradable polyoxalates

Rajput

Ram

Menon

et al. 2018

J. Polym. Sci. Part A: Polym. Chem.

View full text Add to dashboard Cite

Starting from commonly available sugar derivatives, a single step protocol to access a small family of isohexide‐dioxalates (2a–c) has been established. The synthetic competence of 2a–c has been demonstrated by subjecting them to condensation polymerization. Quite surprisingly, the proton NMR of poly(isomannide‐co‐hexane)oxalate revealed a 1:2 ratio between isomannide‐dioxalate (2a) and 1,6‐hexanediol (3a) in the polymer backbone. This intriguing reactivity was found to be an outcome of a cross metathesis reaction between 2a and 3a. The cross metathesis products 3a”[2‐(2‐methoxyacetoxy)ethyl 2‐(2‐hydroxyethoxy)‐2‐(λ3‐oxydanylidene)acetate] and 2a‘(3R,6R)‐6‐hydroxyhexahydrofuro[3,2‐b]‐furan‐3‐yl methyl oxalate were isolated in a control experiment. Based on direct and indirect evidence, and control experiments, an alternative polymerization mechanism is proposed. Polymerization conditions were optimized to obtain polyoxalates P1(2a‐3a)‐P9(2c‐3c) with molecular weights in the range of 14,000–68,000 g/mol, and narrow polydispersities. The identity of the polyoxalates was unambiguously established using 1‐2D NMR spectroscopy, MALDI‐ToF‐MS, and GPC measurements. The practical implication of these polymers is demonstrated by preparing transparent, mechanically robust films. The environmental footprint of the selected polyoxalates was investigated by subjecting them to solution and solid‐state degradation. The polyoxalates were found to be amenable to degradation. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 1584–1592

show abstract

Biodegradability of polyesters comprising a bio-based monomer derived from furfural

Cited by 25 publications

References 60 publications

Synthesis, Physical Properties, and Biodegradability of Biobased Poly(butylene succinate-co-butylene oxabicyclate)

Synthesis, Physical Properties, and Biodegradability of Biobased Poly(butylene succinate-co-butylene oxabicyclate)

Development of High-Molecular-Weight Fully Renewable Biopolyesters Based on Oxabicyclic Diacid and 2,5-Furandicarboxylic Acid: Promising as Packaging and Medical Materials

Cross‐metathesis of biorenewable dioxalates and diols to film‐forming degradable polyoxalates

Contact Info

Product

Resources

About