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

Your Location：

Home >

Browse articles >

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
- Chinese Journal of Polymer Science Vol. 43, Issue 8, Pages: 1320-1332(2025)
- 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：
- DOI：10.1007/s10118-025-3364-0
  CLC：
- Received：20 December 2024，
  
  Revised：16 April 2025，
  
  Accepted：17 April 2025，
  
  Published Online：18 June 2025，
  
  Published：01 August 2025
- Accepted：
Scan QR Code
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

references

Muringayil Joseph, T.; Azat, S.; Ahmadi, Z.; Moini Jazani, O.; Esmaeili, A.; Kianfar, E.; Haponiuk, J.; Thomas, S. Polyethylene terephthalate (PET) recycling: a review. Case Studies in Chem. Environ. Eng. 2024 , 9 , 100673..

Mori, R. Replacing all petroleum-based chemical products with natural biomass-based chemical products: a tutorial review. RSC Sustain. 2023 , 1 , 179−212..

Sarda, P.; Hanan, J. C.; Lawrence, J.G.; Allahkarami, M. Sustainability performance of polyethylene terephthalate, clarifying challenges and opportunities. J. Polym. Sci. 2022 , 60 , 7−31..

Sasanuma, Y. Aromatic Polyester (PET, PTT, and PBT). Wiley, 2023 , p289–p299.

Moshood, T.D.; Nawanir, G.; Mahmud, F.; Mohamad, F.; Ahmad, M.H.; AbdulGhani, A. Sustainability of biodegradable plastics: new problem or solution to solve the global plastic pollution. Curr. Res. Green Sustain. Chem. 2022 , 5 , 100273..

Hahladakis, J.N.; Velis, C.A.; Weber, R.; Iacovidou, E.; Purnell, P. An overview of chemical additives present in plastics: migration, release, fate and environmental impact during their use, disposal and recycling. J. Hazard. Mater. 2018 , 344 , 179−199..

Zhao, X. H.; Wang, Y.; Chen, X. W.; Yu, X. B.; Li, W.; Zhang, S. Y.; Meng, X. Z.; Zhao, Z. M.; Dong, T.; Anderson, A.; Aiyedun, A.; Li, Y. F.; Webb, E.; Wu, Z. L.; Kunc, V.; Ragauskas, A.; Ozcan, S.; Zhu, H. L. Sustainable bioplastics derived from renewable natural resources for food packaging. Matter 2023 , 6 , 9 7−127..

Aziz, T.; Ullah, A.; Ali, A.; Shabeer, M.; Shah, M. N.; Haq, F.; Iqbal, M.; Ullah, R.; Khan, F.U. Manufactures of bio-degradable and bio-based polymers for bio-materials in the pharmaceutical field. J. Appl. Polym. Sci. 2022 , 139 , e52624..

Okolie, O.; Kumar, A.; Edwards, C.; Lawton, L.A.; Oke, A.; McDonald, S.; Thakur, V.K.; Njuguna, J. Bio-based sustainable polymers and materials: from processing to biodegradation. J. Compos. Sci. 2023 , 7 , 213−218..

Unkelbach, G.; Hirth, T. Products and applications of different lignins from biorefineries. EFB Bioecon. J. 2022 , 2 , 100036..

Vasile, C.; Baican, M. Lignins as promising renewable biopolymers and bioactive compounds for high-performance materials. Polymers 2023 , 15 , 3177..

Argyropoulos, D. D. S.; Crestini, C.; Dahlstrand, C.; Furusjö, E.; Gioia, C.; Jedvert, K.; Henriksson, G.; Hulteberg, C.; Lawoko, M.; Pierrou, C.; Samec, J. S. M.; Subbotina, E.; Wallmo, H.; Wimby, M. Kraft lignin: a valuable, sustainable resource, opportunities and challenges. ChemSusChem 2023 , 16 , e202300492..

Nomura, K.; Wang, X. Acyclic Diene Metathesis (ADMET) Polymerization for the synthesis of chemically recyclable bio-based aliphatic polyesters. Catalysts 2024 , 14 , 97..

Le, D.; Samart, C.; Kongparakul, S.; Nomura, K. Synthesis of new polyesters by acyclic diene metathesis polymerization of bio-based α,ω -dienes prepared from eugenol and castor oil (undecenoate). RSC Adv. 2019 , 9 , 10245−10252..

Mialon, L.; Pemba, A.G.; Miller, S.A. Biorenewable polyethylene terephthalate mimics derived from lignin and acetic acid. Green Chem. 2010 , 12 , 1704−1706..

Fodor, C.; Golkaram, M.; Woortman, A. J. J.; van Dijken, J.; Loos, K. Enzymatic approach for the synthesis of biobased aromatic–aliphatic oligo-/polyesters. Polym. Chem. 2017 , 8 , 6795−6805..

Jiang, X.; Guo, Z.; Yuan, Z.; Zhang, X.; Zhu, J.; Wang, J. High thermal resistance biobased copolyester from 2,5-thiophenedicarboxylic acid with excellent gas barrier properties. Eur. Polym. J. 2024 , 220 , 113453..

Djouonkep, L. D. W.; Tamo, A. K.; Doench, I.; Selabi, N. B. S.; Ilunga, E. M.; Lenwoue, A. R. K.; Gauthier, M.; Cheng, Z.; Osorio-Madrazo, A. Synthesis of high performance thiophene-aromatic polyesters from bio-sourced organic acids and polysaccharide-derived diol: characterization and degradability studies. Molecules 2022 , 27 , 325..

Wang, Q.; Li, J.; Wang, J.; Hu, H.; Dong, Y.; O'Young, D. L.; Di Hu; Zhang, X.; Wei, D. Q.; Zhu, J. Biobased biodegradable copolyesters from 2,5-thiophenedicarboxylic acid: effect of aliphatic diols on barrier properties and degradation. Biomacromolecules 2023 , 24 , 5884−5897..

Rillig, M. C.; Ziersch, L.; Hempel, S. Microplastic transport in soil by earthworms. Sci. Rep. 2017 , 7 , 1362..

Ratshoshi, B. K.; Farzad, S.; Görgens, J. F. A techno-economic study of Polybutylene adipate terephthalate (PBAT) production from molasses in an integrated sugarcane biorefinery. Food Bioprod. Process 2024 , 145 , 11−20..

Jian, J.; Xiangbin, Z.; Xianbo, H. An overview on synthesis, properties and applications of poly(butylene-adipate- co -terephthalate)–PBAT. Adv. Ind. Eng. Polym. Res. 2020 , 3 , 19−26..

Ranakoti, L.; Gangil, B.; Mishra, S.K.; Singh, T.; Sharma, S.; Ilyas, R.A.; El-Khatib, S. Critical review on polylactic acid: properties, structure, processing, biocomposites, and nanocomposites. Materials 2022 , 15 , 4312..

Khouri, N. G.; Bahú, J. O.; Blanco-Llamero, C.; Severino, P.; Concha, V. O.; Souto, E. B. Polylactic acid (PLA): properties, synthesis, and biomedical applications—a review of the literature. J. Mol. Struct. 2024 , 1309 , 138243..

Song, J.; Zhang, H.; Niu, M.; Guo, Y.; Li, H. Research progress on vanillin synthesis by catalytic oxidation of lignin: a review. Ind. Crops Prod. 2024 , 214 , 118443..

Fache, M.; Darroman, E.; Besse, V.; Auvergne, R.; Caillol, S.; Boutevin, B. Vanillin, a promising biobased building-block for monomer synthesis. Green Chem. 2014 , 16 , 1987−1998..

Zhang, L.; Cheng, Z.; Wandji Djouonkep, L.D.; Gauthier, M. Synthesis and characterization of aliphatic-aromatic copolyesters based on daidzein. Ind. Eng. Chem. Res. 2024 , 63 , 13445−13458..

Hua, L.; Zhao, D.; Wang, H.; Wei, T. Residues and bioavailability of neonicotinoid pesticide in shaanxi agricultural soil. Water Air Soil Pollut . 2023 , 234 ..

Žaltauskaitė, J.; Sodienė, I. Effects of cadmium and lead on the life-cycle parameters of juvenile earthworm Eisenia fetida. Ecotoxicol. Environ. Saf. 2014 , 103 , 9−16..

Yang, H.; Louhichi, A.; Romano, D.; Rastogi, S. Unveiling the viscoelastic response of nonequilibrium low-entangled polymer melt during its equilibration. Macromolecules 2024 , 57 , 8779−8792..

Zong, X.; Wang, S.; Li, N.; Li, H.; Zhang, X.; He, A. Regulation effects of trans-1, 4-poly(isoprene- co -butadiene) copolymer on the processability, aggregation structure and properties of chloroprene rubber. Polymer 2021 , 213 , 123325..

Zhou, C.; Wei, Z.; Yu, Y.; Shao, S.; Leng, X.; Wang, Y.; Li, Y. Biobased long-chain aliphatic polyesters of 1,12-dodecanedioic acid with a variety of diols: odd-even effect and mechanical properties. Mater. Today Commun. 2019 , 19 , 450−458..

Zhang, M. Y.; Cheng, Z. Z.; Yang, M.; Yu, Q. W.; Tan, Z. P.; Wandji Djouonkep, L. D.; Cheng, J. P.; Liu, P. P.; Ding, L.; Gauthier, M. Synthesis and characterization of poly(1,4-butylene 2,5-furandicarboxylate- co -isosorbide 2,5-furandicarboxylate). J. Wuhan Univ. Technol. Mater Sci. Ed. 2025 , 40 , 582−588..

Andersen, E.; Mikkelsen, R.; Kristiansen, S.; Hinge, M. Real-time ageing of polyesters with varying diols. Mater. Chem. Phys. 2021 , 261 , 124240..

Vaganov, G.; Simonova, M.; Romasheva, M.; Didenko, A.; Popova, E.; Ivan’kova, E.; Kamalov, A.; Elokhovskiy, V.; Vaganov, V.; Filippov, A.; Yudin, V. Influence of molecular weight on thermal and mechanical properties of carbon-fiber-reinforced plastics based on thermoplastic partially crystalline polyimide. Polymers 2023 , 15 , 2922..

Sahu, P.; Sharma, L.; Dawsey, T.; Gupta, R.K. Fully biobased high-molecular-weight p olyesterwith impressive elasticity, thermo-mechanical properties, and enzymatic biodegradability: replacing terephthalate. Macromolecules 2024 , 57 , 9302−9314..

Bhat, R.; Mohan, N.; Sharma, S.; Pratap, A.; Keni, A.P.; Sodani, D. Mechanical testing and microstructure characterization of glass fiber reinforced isophthalic polyester composites. J. Mater. Res. Technol. 2019 , 8 , 3653−3661..

Tachibana, Y.; Yamahata, M.; Kimura, S.; Kasuya, K. Synthesis, physical properties, and biodegradability of biobased poly(butylene succinate- co -butylene oxabicyclate). ACS Sustain. Chem. Eng. 2018 , 6 , 10806−10814..

Llevot, A.; Grau, E.; Carlotti, S.; Grelier, S.; Cramail, H. Selective laccase-catalyzed dimerization of phenolic compounds derived from lignin: towards original symmetrical bio-based (bis) aromatic monomers. J. Mol. Catal. B Enzym: Enzymatic 2016 , 125 , 34−41..

Wang, L.; Cheng, Z.; Djouonkep, L. D. W.; Lan, C.; Cai, S.; Wang, H.; Sun, X.; Gauthier, M. Synthesis and properties of biodegradable polyesters based on orcinol. J. Polym. Environ. 2023 , 31 , 4314−4325..

Xu, H.; Cheng, Z.; Djouonkep, L. D. W.; Gauthier, M.; Zuo, Y.; Tang, W.; Xiang, L. Utilization of lignin-derived methoxybisphenols for the preparation of bio-based polyesters for packaging applications. J. Polym. Environ. 2024 , 33 , 145−160..

Wang, J.; Liu, X.; Zhu, J. Manipulating the properties of poly(1,4-cyclohexylenedimethylene terephthalate) (PCT) just by tuning steric configuration of 1,4-cyclohexanedimethanol (CHDM). Macromol. Chem. Phys . 2018 , 219 , 1800172..

Henrik-Klemens, Å.; Caputo, F.; Ghaffari, R.; Westman, G.; Edlund, U.; Olsson, L.; Larsson, A. The glass transition temperature of isolated native, residual, and technical lignin. Holzforschung 2024 , 78 , 216−230..

Jing, Y.; Zhao, Z.; Cao, X.; Sun, Q.; Yuan, Y.; Li, T. Ultraflexible, cost-effective and scalable polymer-based phase change composites via chemical cross-linking for wearable thermal management. Nat. Commun. 2023 , 14 , 8060..

Cholakova, D.; Denkov, N. Polymorphic phase transitions in triglycerides and their mixtures studied by SAXS/WAXS techniques: in bulk and in emulsions. Adv. Colloid Interface Sci. 2024 , 323 , 103071..

Zhao, C.; Yang, S.; Qin, W.; Zou, G. Study on synthesis and properties of oxybis benzoic aromatic polyesters. Polym. Sci. Ser. B 2023 , 65 , 438−449..

Yang, Y.; Cheng, Z.; Wandji Djouonkep, L.D.; Gauthier, M. Synthesis and properties of bio-based polyesters from a 2,4-dihydroxyacetophenone derivative. J. Macromol. Sci., Part A 2024 , 61 , 555−564..

Djouonkep, L.D.W.; Tchameni, A.P.; Selabi, N.B.S.; Tamo, A.K.; Doench, I.; Cheng, Z.; Gauthier, M.; Xie, B.; Osorio-Madrazo, A. Bio-based degradable poly(ether-ester)s from melt-polymerization of aromatic ester and ether diols. Int. J. Mol. Sci. 2022 , 23 , 8967..

Wang, J.; Liu, X.; Jia, Z.; Sun, L.; Zhang, Y.; Zhu, J. Modification of poly(ethylene 2,5-furandicarboxylate) (PEF) with 1,4-cyclohexanedimethanol: influence of stereochemistry of 1,4-cyclohexylene units. Polymer 2018 , 137 , 173−185..

Wandji Djouonkep, L.D.; Cheng, Z.; Gauthier, M. Tuning interphase behavior of thermo-responsive block polym er assemblies for enhanced filter cake performance. J. Mol. Liq. 2025 , 428 , 127573..

Reddy, C. N.; Kallem, P.; Mounika, K. V. S. S. N.; Muqeet, A.; Raj, J. C. J.; Aishwarya, C. V. S.; Gupta, R. K.; Polisetti, V.; Mishra, B.; Yadavalli, R.; Mandal, S. K.; Hedenqvist, M. S.; Banat, F. Review of microplastic degradation: understanding metagenomic approaches for microplastic degrading organisms. Polym. Test. 2023 , 128 , 108223..

Purohit, J.; Chattopadhyay, A.; Teli, B. Metagenomic exploration of plastic degrading microbes for biotechnological application. Curr. Genomics 2020 , 21 , 253−270..

Liwarska-Bizukojc, E.; Bernat, P.; Jasińska, A. Effect of bio-based microplastics on earthworms Eisenia andrei. Sci. Total Environ. 2023 , 898 , 165423..

Khaldoon, S.; Lalung, J.; Maheer, U.; Kamaruddin, M. A.; Yhaya, M. F.; Alsolami, E. S.; Alorfi, H. S.; Hussein, M. A.; Rafatullah, M. A review on the role of earthworms in plastics degradation: issues and challenges. Polymers 2022 , 14 , 4770..

Dimassi, S N.; Hahladakis, J. N.; Yahia, M. N. D.; Ahmad, M. I.; Sayadi, S.; Al-Ghouti, M. A. Degradation-fragmentation of marine plastic waste and their environmental implications: a critical review. Arab. J. Chem. 2022 , 15 , 104262..

Talsness, C. E.; Andrade, A. J. M.; Kuriyama, S. N.; Taylor, J. A.; vom Saal, F. S. Components of plastic: experimental studies in animals and relevance for human health. Philos. Trans. R. Soc. Lond. B Biol. Sci. 2009 , 364 , 2079−2096..

Deji-Oloruntoba, O.; Agidigbi, T.S.; Jang, M. Microplastics and nano-plastics contamination in foods: current understanding of the health impact on human and potential solutions. EJNFS 2024 , 16 , 11−31..

Courtene-Jones, W.; Falco, F. de; Burgevin, F.; Handy, R. D.; Thompson, R.C. Are biobased microfibers less harmful than conventional plastic microfibers: evidence from earthworms. Environ. Sci. Technol. 2024 , 58 , 20366−20377..

Mohamed, I. A.; Soliman, H. A. M.; Hana, M.; Lee, J. S.; Sayed, A. E. D. H. Toxicity of mixture of polyethylene microplastics and Up Grade® pesticide on Oreochromis niloticus juvenile: I. Hemato-biochemical and histopathological alterations. Environ. Toxicol. Pharmacol. 2023 , 101 , 104213..

Views

Downloads

CSCD

Alert me when the article has been cited

Submit

Tools

Publicity Resources

Superior Toughened Biodegradable Poly(L-lactic acid)-based Blends with Enhanced Melt Strength and Excellent Low-temperature Toughness via In situ Reaction Compatibilization

Architecting Branch Structure in Terpolymer of CO₂, Propylene Oxide and Phthalic Anhydride: An Enhancement in Thermal and Mechanical Performances

Mechanical Properties, Crystallization and Biodegradation Behavior of the Polylactide/Poly(3-hydroxybutyrate-co-4-hydroxybutyrate)/Poly(butylene adipate-co-terephthalate) Blown Films

Preparation of Chlorinated Poly(propylene carbonate) and Its Distinguished Properties

Related Author

Hui-Xuan Zhang

Li-Song Dong

Hui-Liang Zhang

Li-Jing Han

Yan Zhao

Hong-Wei Pan

Xiang-Yu Yan

Ye Zhang

Related Institution

School of Materials Science and Engineering, Changchun University of Technology

Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences

The key laboratory of Low-carbon Chemistry & Energy Conservation of Guangdong Province, State Key Laboratory of Optoelectronic Materials and Technologies, School of Materials Science and Engineering, Sun Yat-sen University

University of Science and Technology of China

Zhejiang Zhongke Applied Chemistry Technology Co., Ltd.

⁰