Epoxy-functionalized Cyclohexane-based Ricinoleate Plasticizer: Synthesis, Performance Evaluation, and Plasticizing Mechanism

Zhuo-Kai Wang; Ying-Yong Jiang; Wen-Nan Du; Yao-Bin Wang; Xing-Chen Bai; Cheng-Wei Song; Zhi-Peng Jiang; Liang Ren; Sai-Nan Cui; Feng-Xiang Gao

doi:10.1007/s10118-026-3698-2

Your Location：

Home >

Browse articles >

Epoxy-functionalized Cyclohexane-based Ricinoleate Plasticizer: Synthesis, Performance Evaluation, and Plasticizing Mechanism

RESEARCH ARTICLE | Updated：2026-08-31

- Epoxy-functionalized Cyclohexane-based Ricinoleate Plasticizer: Synthesis, Performance Evaluation, and Plasticizing Mechanism
- Chinese Journal of Polymer Science Vol. 44, Issue 9, Pages: 3075-3091(2026)
- Affiliations：
  
  a.School of Chemical Engineering, Changchun University of Technology, Changchun 130102, China
  b.Engineering Research Center for synthetic resin and special fiber, Ministry of Education, Changchun University of Technology, Changchun 130102, China
  c.Research Institute of Jilin Petrochemical Company, PetroChina, Jilin 132012, China
  d.Key Laboratory of Polymer Ecomaterials, Changchun, Institute of Applied Chemistry CAS, Chinese Academy of Sciences, Changchun 130022, China
- Author bio：
  
  renl@ccut.edu.cn (L.R.)
  gfx26@ciac.ac.cn (F.X.G.)
- Funds：
- DOI：10.1007/s10118-026-3698-2
  CLC：
- Received：28 January 2026，
  
  Accepted：04 April 2026，
  
  Online First：20 May 2026，
  
  Published：05 September 2026
- Accepted：
Scan QR Code
Wang, Z. K.; Jiang, Y. Y.; Du, W. N.; Wang, Y. B.; Bai, X. C.; Song, C. W.; Jiang, Z. P.; Ren, L.; Cui, S. N.; Gao, F. X. Epoxy-functionalized cyclohexane-based ricinoleate plasticizer: synthesis, performance evaluation, and plasticizing mechanism. Chinese J. Polym. Sci. 2026, 44, 3075–3091

Zhuo-Kai Wang, Ying-Yong Jiang, Wen-Nan Du, et al. Epoxy-functionalized Cyclohexane-based Ricinoleate Plasticizer: Synthesis, Performance Evaluation, and Plasticizing Mechanism[J]. Chinese Journal of Polymer Science, 2026, 44(9): 3075-3091.
Wang, Z. K.; Jiang, Y. Y.; Du, W. N.; Wang, Y. B.; Bai, X. C.; Song, C. W.; Jiang, Z. P.; Ren, L.; Cui, S. N.; Gao, F. X. Epoxy-functionalized cyclohexane-based ricinoleate plasticizer: synthesis, performance evaluation, and plasticizing mechanism. Chinese J. Polym. Sci. 2026, 44, 3075–3091 DOI： 10.1007/s10118-026-3698-2.

Zhuo-Kai Wang, Ying-Yong Jiang, Wen-Nan Du, et al. Epoxy-functionalized Cyclohexane-based Ricinoleate Plasticizer: Synthesis, Performance Evaluation, and Plasticizing Mechanism[J]. Chinese Journal of Polymer Science, 2026, 44(9): 3075-3091. DOI： 10.1007/s10118-026-3698-2.

摘要

A novel molecular design integrating flexible non-edible backbone

alicyclic rigid core

and epoxy groups breaks the performance-sustainability trade-off. The optimal plasticizer lowers

of poly(vinyl chloride) (PVC) by 30%

increases elongation

50-fold

and improves efficiency by 20.7% versus DOTP.

Abstract

The molecular design of bio-based plasticizers often involves a trade-off between key performance and sustainability. Herein

we propose a novel molecular design strategy that breaks this contradiction by integrating a flexible backbone derived from non-edible sources

sustainable alicyclic rigid core

and epoxy groups. A series of epoxy-functionalized cyclohexane-based ricinoleate plasticizers

epoxyacetyl ricinoleic

acid cyclohexanol ester (EACHR)

epoxyacetyl ricinoleic acid cyclohexanediol ester (EACHDR)

and epoxyacetyl ricinoleic acid cyclohexanedimethanol ester (EACHDMR)

were synthesized. When evaluated in poly(vinyl chloride) (PVC) as a demanding validation platform

the optimal plasticizer (EACHDMR) achieved comprehensive performance

which reduced the glass transition temperature (

) by 30%

increased the elongation at break by more than 50-fold

and enhanced the notched impact strength by over 35-fold compared to an unplasticized PVC sample. Importantly

EACHDMR exhibited lower migration and 20.7% higher plasticizing efficiency than the commercial benchmark dioctyl terephthalate (DOTP). This study demonstrated that by rationally integrating rigid cores

flexible fatty acid chains

and polar groups

it is possible to successfully balance performance and sustainability

providing a new design strategy for developing high-performance and sustainable alternatives to traditional plasticizers.

关键词

Keywords

references

Wang, Y.; Qian, H. Phthalates and their impacts on human health. Healthcare. 2021 , 9 , 603..

Zia, A. I.; Abdul Rahman, M. S.; Mukhopadhyay, S. C.; Yu, P. L.; Al-Bahadly, I.; Gooneratne, C.; Kosel, J.; Taishan, L. Electrochemical impedance spectroscopy based MEMS sensors for phthalates detection in water and juices. J. Phys. Conf. Ser. 2013 , 439 , 012026..

Sabi, G. J.; Simões, A .L. A.; Gorup, L. F.; da Silva, W. A.; Mendes, A. A. Production of benzyl-based esters from used soybean cooking oil as renewable plasticizers for flexible PVC films: exploring new applications for lipases in emerging technologies. Int. J. Biol. Macromol. 2025 , 292 , 139233..

Yang, Y.; Tao, Y.; Yang, R.; Yi, X.; Zhong, G.; Gu, Y.; Zhang, Y. Ca 2+ homeostasis imbalance induced by Pparg: A key factor in di (2-ethylhexyl) phthalate (DEHP)-induced cardiac dysfunction in zebrafish larvae. Sci. Total Environ. 2024 , 918 , 170436..

Mo, L.; Fang, L.; Yao, W.; Nie, J.; Dai, J.; Liang, Y.; Qin, L. LC-QTOF/MS-based non-targeted metabolomics to explore the toxic effects of di(2-ethylhexyl) phthalate (DEHP) on Brassica chinensis L. Sci. Total Environ. 2024 , 918 , 170817..

Gao, X.; Cui, L.; Mu, Y.; Li, J.; Zhang, Z.; Zhang, H.; Xing, F.; Duan, L.; Yang, J. Cumulative health risk in children and adolescents exposed to bis(2-ethylhexyl) phthalate (DEHP). Environ Res. 2023 , 237 , 116865..

Fiorentino, G.; Ripa, M.; Ulgiati, S. Chemicals from biomass: technological versus environmental feasibility. A review. Biofuels. 2017 , 11 , 195−214..

Djouonkep, L.D.W.; Tamo, C.T.; Simo, B.E.; Issah, N.; Tchouagtie, M.N.; Selabi, N.B.S.; Doench, I.; Kamdem Tamo, A.; Xie, B.; Osorio-Madrazo, A. Synthesis by melt-polymerization of a novel series of bio-based and biodegradable thiophene-containing copolyesters with promising gas barrier and high Thermomechanical Properties. Molecules 2023 , 28 , 1825..

Mujtaba, M.; Lipponen, J.; Ojanen, M.; Puttonen, S.; Vaittinen, H. Trends and challenges in the development of bio-based barrier coating materials for paper/cardboard food packaging; a review. Sci. Total Environ. 2022 , 851 , 158328..

[Li, D.; Panchal, K.; Vasudevan, N.; Mafi, R.; Xi, L. Effects of molecular design parameters on plasticizer performance in poly(vinyl chloride): a comprehensive molecular simulation study. Chem. Eng. Sci. 2021 , 249 , 117334..

Chen, Y.; Zhou, S.; Pan, S.; Zhao, D.; Wei, J.; Zhao, M.; Fan, H. Methods for determination of plasticizer migration from polyvinyl chloride synthetic materials: a mini review. J. Leather Sci. Eng. 2022 , 4 , 8..

Rahman, M.; Brazel, C.S. The plasticizer market: an assessment of traditional plasticizers and research trends to meet new challenges. Prog. Polym. Sci. 2004 , 29 , 1223−1248..

He, W.; Zhu, G.; Gao, Y.; Wu, H.; Fang, Z.; Guo, K. Green plasticizers derived from epoxidized soybean oil for poly(vinyl chloride): continuous synthesis and evaluation in PVC films. Chem. Eng. J. 2020 , 380 , 122532..

Quiles-Carrillo, L.; Duart, S.; Montanes, N.; Torres-Giner, S.; Balart, R. Enhancement of the mechanical and thermal properties of injection-molded polylactide parts by the addition of acrylated epoxidized soybean oil. Mater. Des. 2018 , 140 , 54−63..

Feng, G. D.; Hu, Y.; Zhou, Y. H. Preparation and application of epoxy oil-based fire-retardant plasticizer for PVC. Asian J. Chem. 2015 , 19 , S5−481-S5-485..

Ma, Y.; Kou, Z.; Jia, P.; Zhou, J. Effect of benzene ring and alkane chain contained bio-based plasticizers on the plasticizing performance of polyvinyl chloride films. Chem. Pap. 2021 , 75 , 5515−5521..

Hou, B.; Wang, Y.; Li, B.; Gong, T.; Wu, J.; Li, J. Synthesis of novel L-lactic acid-based plasticizers and their effects on the flexibility, crystallinity, and optical transparency of poly(lactic acid). Int. J. Biol. Macromol. 2024 , 273 , 132826..

Tan, S.X.; Andriyana, A.; Ong, H.C.; Lim, S.; Pang, Y.L.; Ngoh, G.C. A comprehensive review on the emerging roles of nanofillers and plasticizers towards sustainable starch-based bioplastic fabrication. Polymers. 2022 , 14 , 664..

Amri, M.; Al-Edrus, S.; Luqman Chuah, A.; Md Yasin, F.; Lee, S.H. Jatropha oil as a substituent for palm oil in biobased polyurethane. Int. J. Polym. Sci. 2021 , 2021 , 6655936..

Caicho-Caranqui, J.; Taipe, L.A.; Mena, K.A.; Ponce, S.; Mora, J.R.; Negrete-Bolagay, D.; Zamora-Mendoza, L.; Guerrero, V.H.; Ponton Bravo, P.I.; Pasquel, D.; Paredes, J.; Alvarez Barreto, J.F.; Zambrano, C.; Alexis, F. Towards sustainable bioplasticizers from biomass to polymers applications: a review. Sustain. Mater. Technol. 2025 , 43 , e01194..

Zhang, Z.; Jiang, P.; Liu, D.; Feng, S.; Zhang,P.; Wang, Y.; Fu, J.; Agus, H. Research progress of novel bio-based plasticizers and their applications in poly(vinyl chloride). J. Mater. Sci. 2021 , 56 , 10155−10182..

Deshmukh, A.; Ganure, V. A review of the literature on eranda(Ricinus Communis Linn.,) and its therapeutic applications and phytochemical components. Int. Ayurved. Med. J. 2023 , 11 , 1249−1254..

Dwivedi, N.N.; Sharma, R. A beneficial action of ricinus communis. Int. J. Res. Rev. 2022 , 9 , 159−168..

Jia, P.; Hu, L.; Zhang, M.; Feng, G.; Zhou, Y. Phosphorus containing castor oil based derivatives: potential non-migratory flame retardant plasticizer. Eur. Polym. J. 2017 , 87 , 209−220..

Yamamoto, A.; Nemoto, K.; Yoshida, M.; Tominaga, Y.; Imai, Y.; Ata, S.; Takenaka, Y.; Abe, H.; Sato, K. Improving thermal and mechanical properties of biomass-based polymers using structurally ordered polyesters from ricinoleic acid and 4-hydroxycinnamic acids. RSC Adv. 2020 , 10 , 36562−36570..

Jing, Y.; Xia, Q.; Xie, J.; Liu, X.; Guo, Y.; Zou, J. J.; Wang, Y. Robinson annulation-directed synthesis of jet-fuel-ranged alkylcyclohexanes from biomass-derived chemicals. ACS Catal. 2018 , 8 , 3280−3285..

Li, X.; Guo, T.; Xia, Q.; Liu, X.; Wang, Y. One-pot catalytic transformation of lignocellulosic biomass into alkylcyclohexanes and polyols. ACS Sustain. Chem. Eng. 2018 , 6 , 4390−4399..

Chaiyaraksa, C.; Sriprom, P.; Boonkaen, F.; Laemsri, A.; Smingkaew, A.; Chokelarb, W.; Assawasaengrat, P. Cleaner bio-based plasticizer synthesis from waste cooking oil to substitute toxic dioctyl phthalate in PVC film. Key Eng. Mater. 2025 , 1017 , 103−108..

Cruz, P. P. R.; da Silva, L. C.; Fiuza-Jr, R. A.; Polli, H. Thermal dehydrochlorination of pure PVC polymer: Part I—thermal degradation kinetics by thermogravimetric analysis. J. Appl. Polym. Sci. 2021 , 138 , e50598..

Yu, J.; Sun, L.; Ma, C.; Qiao, Y.; Yao, H. Thermal degradation of PVC: a review. Waste Manag. 2016 , 48 , 300−314..

Kwon, C.W.; Chang, P.-S. Influence of alkyl chain length on the action of acetylated monoglycerides as plasticizers for poly (vinyl chloride) food packaging film. Food Packag. Shelf Life 2021 , 27 , 100619..

Qian, B.; Zhang, J.; Wu, M.; Liu, J.; Wu, Q.; Yang, J. Synthesis, characterization and performance evaluation of “crab” bio-based poly(vinyl chloride) plasticizer based on sustainable lactic acid. Polymer. 2023 , 283 , 126246..

Jia, P.; Hu, L.; Shang, Q.; Wang, R.; Zhang, M.; Zhou, Y. Self-Plasticization of PVC materials via chemical modification of mannich base of cardanol butyl ether. ACS Sustain. Chem. Eng. 2017 , 5 , 6665−6673..

Cai, D. L.; Yue, X.; Hao, B.; Ma, P. C. A sustainable poly(vinyl chloride) plasticizer derivated from waste cooking oil. J. Clean. Prod. 2020 , 274 , 122781..

Guan, C.; Xiao, C.; Liu, X.; Hu, Z.; Wang, R.; Wang, C.; Xie, C.; Cai, Z.; Li, W. Non-Covalent interactions between polyvinyl chloride and conjugated polymers enable excellent mechanical properties and high stability in organic solar cells. Angew. Chem. Int. Ed. 2023 , 62 , e202312357..

Fox, T.G., Jr.; Flory, P.J. Second-order transition temperatures and related properties of polystyrene. I. Influence of Molecular Weight. J. Appl. Phys. 1950 , 21 , 581−591..

Xuan, W.; Hakkarainen, M.; Odelius, K. Levulinic acid as a versatile building block for plasticizer design. ACS Sustain. Chem. Eng. 2019 , 7 , 12552−12562..

Lenzi, L.; Degli Esposti, M.; Braccini, S.; Siracusa, C.; Quartinello, F.; Guebitz, G.M.; Puppi, D.; Morselli, D.; Fabbri, P. Further step in the transition from conventional plasticizers to versatile bioplasticizers obtained by the valorization of levulinic acid and glycerol. ACS Sustain. Chem. Eng. 2023 , 11 , 9455−9469..

Edo, G. I.; Ndudi, W.; Ali, A. B. M.; Yousif, E.; Zainulabdeen, K.; Onyibe, P. N.; Ekokotu, H. A.; Isoje, E. F.; Igbuku, U. A.; Essaghah, A. E. A.; Ahmed, D. S.; Umar, H.; Ozsahin, D.U. Poly(vinyl chloride) (PVC): an updated review of its properties, polymerization, modification, recycling, and applications. J. Mater. Sci. 2024 , 59 , 21605−21648..

Daniels, P. A brief overview of theories of PVC plasticization and methods used to evaluate PVC-Plasticizer interaction. J. Vinyl Addit. Technol. 2009 , 15 , 219−223..

Zhou, H.; Xu, P.; Xie, S.; Feng, Z.; Wang, D. Mecha nical performance and energy absorption properties of structures combining two Nomex honeycombs. Compos. Struct. 2018 , 185 , 524−536..

Jiang, Y.; Gao, F.; Ren, L.; Liu, Q.; Song, T.; Shen, Y.; Du, W.; Wang, Y.; Zhang, M. Novel environmentally sustainable plasticizers based on ricinoleic acid for poly(vinyl chloride): structure and properties. New J. Chem. 2024 , 48 , 4960−4975..

Lourdin, D.; Coignard, L.; Bizot, H.; Colonna, P. Influence of equilibrium relative humidity and plasticizer concentration on the water content and glass transition of starch materials. Polymer. 1997 , 38 , 5401−5406..

Burns, K.; Potgieter, J.H.; Potgieter-Vermaak, S.; Ingram, I.; Liauw, C. A comparative assessment of the use of suitable analytical techniques to evaluate plasticizer compatibility. J. Appl. Polym. Sci. 2023 , 140 , 54104..

O’Mahony, C. T.;Borah, D.; Morris, M. A. Microphase separation of a PS-b-PFS block copolymer via solvent annealing: effect of solvent, substrate, and exposure time on morphology. Int. J. Polym. Sci. 2015 , 2015 , 270891..

Mackey, J.; Grover, D.; Pruneda, G.; Zenk, E.; Nagy, Z. K. Continuous extraction of 2-chloroethyl isocyanate for 1-(2-chloroethyl)-3-cyclohexylurea purification. Chem. Eng. Process. Process Intensif. 2023 , 183 , 109225..

Yang, Y.; Zhang, C. L.; Han, Y.; Weng, Y. X. Plasticizing and thermal stabilizing effect of bio-based epoxidized cardanol esters on PVC. Polym. Adv. Technol. 2022 , 34 , 181−194..

Sun, S. Y.; Weng, Y. X.; Zhang, C. L. Recent advancements in bio-based plasticizers for polylactic acid (PLA): a review. Polym. Test. 2024 , 140 , 108603..

Abou-Rachid, H.; Lussier, L.-S.; Ringuette, S.; Lafleur-Lambert, X.; Jaidann, M.; Brisson, J. On the correlation between miscibility and solubility properties of energetic plasticizers/polymer blends: modeling and simulation studies. Propellants Explos. Pyrotech. 2008 , 33 , 301−310..

Yang, W.; Chen, X.; Song, X.; Hu, Y.; Pei, J.; Chen, J. Molecular dynamics study on the physical compatibility of SEBS/plasticizer blend systems. J. Mol. Model. 2024 , 30 , 293..

Jarray, A.; Gerbaud, V.; Hemati, M. Polymer-plasticizer compatibility during coating formulation: A multi-scale investigation. Prog. Org. Coat. 2016 , 101 , 195−206..

Views

103

Downloads

CSCD

Alert me when the article has been cited

Submit

Tools

Publicity Resources

15.6% Efficiency Polythiophene-based All-polymer Solar Cells

Advances in Green-Solvent-Processable All-Polymer Solar Cells

Toward Rational and Modular Molecular Design in Soft Matter Engineering

Sequence-encoded Conformation Pathways in Viscoelastic Microphase Separation of Multiblock Copolymers

Silk Sericin-inspired Poly-β-homoserine for Protein Protection

Related Author

He Yan

Xi-Yue Yuan

Lang-Heng Pan

Jiang-Long Li

Chao Li

Dong-Sheng Xie

Kang-Zhe Liu

Yu-Chuan Tian

Related Institution

Sinopec Shanghai Res Inst Petrochem Technol Co., Ltd.

Institute of Polymer Optoelectronic Materials and Devices, Guangdong Basic Research Center of Excellence for Energy & Information Polymer Materials, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology

School of Electronic Science and Engineering (School of Microelectronics), South China Normal University

Hangzhou International Innovation Institute, Beihang University

Department of Chemistry and Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, Hong Kong University of Science and Technology, Clear Water Bay, Kowloon

⁰