Biobased Polyesters Derived from 2-Methoxyhydroquinone: Impact of Cyclic and Alkyl Chain Segments on Their Thermomechanical Properties, Biodegradability, and Ecotoxicity

Hao-Ming Xu; Zheng-Zai Cheng; Zi-Ting Zhou; Lesly Dasilva Wandji Djouonkep; Mario Gauthier

doi:10.1007/s10118-025-3364-0

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Biobased Polyesters Derived from 2-Methoxyhydroquinone: Impact of Cyclic and Alkyl Chain Segments on Their Thermomechanical Properties, Biodegradability, and Ecotoxicity

RESEARCH ARTICLE | Updated：2025-07-26

- Biobased Polyesters Derived from 2-Methoxyhydroquinone: Impact of Cyclic and Alkyl Chain Segments on Their Thermomechanical Properties, Biodegradability, and Ecotoxicity
- Biobased Polyesters Derived from 2-Methoxyhydroquinone: Impact of Cyclic and Alkyl Chain Segments on Their Thermomechanical Properties, Biodegradability, and Ecotoxicity
- 高分子科学（英文） 2025年43卷第8期页码：1320-1332
- Affiliations：
  
  Institute of Fine Organic Chemicals & Organic Materials, School of Chemistry and Chemical Engineering, Wuhan University of Science and Technology, Wuhan 430081, China
- Author bio：
  
  hbchengzz@163.com (Z.Z.C.)
  dasilvasilva3008@wust.edu.cn (L.D.W.D)
- Funds：
  
  This work was financially supported by State Administration of Foreign Experts Affairs (SAFEA) through the High-End Foreign Expert Program (No. BG2021227001) and postdoctoral funding from Wuhan University of Science and Technology (No. 105008701).;Electronic supplementary information (ESI) is available free of charge in the online version of this article at http://doi.org/10.1007/s10118-025-3364-0.
- DOI：10.1007/s10118-025-3364-0
  中图分类号：
- 收稿日期：2024-12-20，
  
  修回日期：2025-04-16，
  
  录用日期：2025-04-17，
  
  网络出版日期：2025-06-18，
  
  纸质出版日期：2025-08-01
- Accepted：
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Xu, H. M.; Cheng, Z. Z.; Zhou, Z. T.; Djouonkep, L. D. W.; Gauthier, M. Biobased polyesters derived from 2-methoxyhydroquinone: impact of cyclic and alkyl chain segments on their thermomechanical properties, biodegradability, and ecotoxicity. Chinese J. Polym. Sci. 2025, 43, 1320–1332

Hao-Ming Xu, Zheng-Zai Cheng, Zi-Ting Zhou, et al. Biobased Polyesters Derived from 2-Methoxyhydroquinone: Impact of Cyclic and Alkyl Chain Segments on Their Thermomechanical Properties, Biodegradability, and Ecotoxicity[J]. Chinese journal of polymer science, 2025, 43(8): 1320-1332.
Xu, H. M.; Cheng, Z. Z.; Zhou, Z. T.; Djouonkep, L. D. W.; Gauthier, M. Biobased polyesters derived from 2-methoxyhydroquinone: impact of cyclic and alkyl chain segments on their thermomechanical properties, biodegradability, and ecotoxicity. Chinese J. Polym. Sci. 2025, 43, 1320–1332 DOI： 10.1007/s10118-025-3364-0.

Hao-Ming Xu, Zheng-Zai Cheng, Zi-Ting Zhou, et al. Biobased Polyesters Derived from 2-Methoxyhydroquinone: Impact of Cyclic and Alkyl Chain Segments on Their Thermomechanical Properties, Biodegradability, and Ecotoxicity[J]. Chinese journal of polymer science, 2025, 43(8): 1320-1332. DOI： 10.1007/s10118-025-3364-0.

摘要

The study demonstrated the tunability of cyclic and alkyl chain segments in novel biobased polyesters derived from renewable 2-methoxyhydroquinone

and how their thermomechanical characteristics

biodegradability

and ecotoxicity

can be enhanced to serve as a potential PET mimics.

Abstract

To enhance the properties of bio-based polyesters

enabling them to more closely mimic the characteristics of terephthalate-based materials

a series of aliphatic-aromatic copolyesters (P

–P

) were synthesized

via

melt polycondensation. Diester monomers M and N were synthesized

via

the Williamson reaction

using lignin-derived 2-methoxyhydroquinone

methyl 4-chloromethylbenzoate

and methyl chloroacetate as starting materials. Hydroquinone bis(2-hydroxyethyl)ether (HQEE) and 1

4-cyclohexanedimethanol (CHDM) were employed as cyclic segments

while 1

4-butanediol (BDO) and 1

6-hexanediol (HDO) served as alkyl segments within the copolymer structures. The novel copolyesters exhibited molecular weights (

) in the range of 5.25×10

–5.87×10

g/mol

with polydispersity indices spanning from 2.50–2.66. Evaluation of the structural and thermomechanical properties indicated that the inclusion of alkyl segments induced a reduction in both crystallinity and molecular weight

while significantly improving the flexibility

whereas cyclic segments enhanced the processability of the copolyesters. Copolyesters P

and P

due to the presence of rigid segments (HQEE and CHDM)

displayed relatively high glass transition temperatures (

80 °C) and melting temperatures (

170 °C). Notably

incorporating CHDM

exhibited superior elongation properties (272%)

attributed to the enhanced chain mobility resulting from its

trans

-conformation

while P

was found to be likely brittle owing to excessive chain stiffness. Biodegradability assessment using earthworms as bioindicators revealed that the copolyesters demonstrated moderate degradation profiles

with P

exhibiting a degradation rate of 4.82%

followed by P

at 4.07%

at 3.65%

and P

at 3.17%. The higher degradation rate of P

was attributed to its relatively larger d-spacing and lower toxicity

which facilitated enzymatic hydrolytic attack by microorganisms. These findings highlight the significance of optimizing the structural chain segments within aliphatic-aromatic copolyesters. By doing so

it is possible to significantly enhance their properties and performance

offering viable bio-based alternatives to petroleum-based polyesters such as polyethylene terephthalate (PET).

关键词

Keywords

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