Synthesis and evaluation of epoxidized vegetable oleic acid as a novel environmental benign plasticizer for polyvinyl chloride
Shan Feng
R&D Department, Key Laboratory of Synthesis Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, China
Contribution: Conceptualization (lead), Data curation (lead), Formal analysis (lead), Funding acquisition (equal), Investigation (lead), Methodology (lead), Software (lead), Validation (lead), Writing - original draft (lead)
Search for more papers by this authorCorresponding Author
Pingping Jiang
R&D Department, Key Laboratory of Synthesis Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, China
Correspondence
Pingping Jiang and Pingbo Zhang, R&D Department, Key Laboratory of Synthesis Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, China.
Email: [email protected] and [email protected]
Contribution: Funding acquisition (lead), Project administration (lead), Resources (lead), Writing - review & editing (lead)
Search for more papers by this authorCorresponding Author
Pingbo Zhang
R&D Department, Key Laboratory of Synthesis Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, China
Correspondence
Pingping Jiang and Pingbo Zhang, R&D Department, Key Laboratory of Synthesis Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, China.
Email: [email protected] and [email protected]
Search for more papers by this authorMinjia Lu
R&D Department, Key Laboratory of Synthesis Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, China
Contribution: Investigation (supporting)
Search for more papers by this authorZhixuan Cui
R&D Department, Key Laboratory of Synthesis Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, China
Contribution: Investigation (supporting)
Search for more papers by this authorJie Pan
R&D Department, Wuxi Jiasheng High-tech Modified Materials Co., Ltd., Wuxi, China
Contribution: Investigation (supporting)
Search for more papers by this authorLingen Pan
R&D Department, Wuxi Jiasheng High-tech Modified Materials Co., Ltd., Wuxi, China
Contribution: Investigation (supporting)
Search for more papers by this authorShan Feng
R&D Department, Key Laboratory of Synthesis Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, China
Contribution: Conceptualization (lead), Data curation (lead), Formal analysis (lead), Funding acquisition (equal), Investigation (lead), Methodology (lead), Software (lead), Validation (lead), Writing - original draft (lead)
Search for more papers by this authorCorresponding Author
Pingping Jiang
R&D Department, Key Laboratory of Synthesis Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, China
Correspondence
Pingping Jiang and Pingbo Zhang, R&D Department, Key Laboratory of Synthesis Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, China.
Email: [email protected] and [email protected]
Contribution: Funding acquisition (lead), Project administration (lead), Resources (lead), Writing - review & editing (lead)
Search for more papers by this authorCorresponding Author
Pingbo Zhang
R&D Department, Key Laboratory of Synthesis Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, China
Correspondence
Pingping Jiang and Pingbo Zhang, R&D Department, Key Laboratory of Synthesis Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, China.
Email: [email protected] and [email protected]
Search for more papers by this authorMinjia Lu
R&D Department, Key Laboratory of Synthesis Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, China
Contribution: Investigation (supporting)
Search for more papers by this authorZhixuan Cui
R&D Department, Key Laboratory of Synthesis Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, China
Contribution: Investigation (supporting)
Search for more papers by this authorJie Pan
R&D Department, Wuxi Jiasheng High-tech Modified Materials Co., Ltd., Wuxi, China
Contribution: Investigation (supporting)
Search for more papers by this authorLingen Pan
R&D Department, Wuxi Jiasheng High-tech Modified Materials Co., Ltd., Wuxi, China
Contribution: Investigation (supporting)
Search for more papers by this authorFunding information: The Postgraduate Research & Practice Innovation Program of Jiangsu Province, Grant/Award Number: SJCX22_1113; MOE & SAFEA for the 111 Project; International Exchange and Cooperation Projects, Grant/Award Number: BX 2019018
Abstract
A bio-based plasticizers, acetyl-oleate triethylene glycol (AOT), was successfully synthesized by using oleic acid as a raw material through esterification, epoxidation, and acetylation. Its structure was analyzed by Fourier transform infrared spectroscopy and 1H nuclear magnetic resonance. The plasticizing performances of this plasticizer was compared with those of two commercial ones: dioctyl terephthalate (DOTP) and dioctyl adipate (DOA). This was done by blending these plasticizers with PVC, respectively. Thermal gravimetric analysis results showed that the 5% weight loss temperature of PVC with AOT was 53°C higher than that of DOA and 36°C higher than that of DOTP. The tensile results showed that the AOT plasticized PVC had excellent stretchability: its elongation at break with 50 phr AOT reached 697.7%. Furthermore, its transmittance was as high as 90%, showing better compatibility of ATO with PVC.
Open Research
DATA AVAILABILITY STATEMENT
The data that support the findings of this study are available in the supplementary material of this article.
Supporting Information
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app53331-sup-0001-supinfo.docxWord 2007 document , 1.5 MB | Appendix S1 Supporting information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
REFERENCES
- 1Y. Hao, A. Tian, J. Zhu, J. Fan, Y. Yang, Ind. End. Chem. Res. 2020, 59, 18290.
- 2M. W. Halloran, J. A. Nicell, R. L. Leask, M. Marić, J. Appl. Polym. Sci. 2022, 139, e52778.
- 3S. Pan, D. Hou, J. Chang, Z. Xu, S. Wang, S. Yan, Q. Zeng, Z. Wang, Y. Chen, Green Chem. 2019, 21, 6430.
- 4Y. Ma, Z. Kou, P. Jia, J. Zhou, Chem. Pap. 2021, 75, 5515.
- 5Z. He, Y. Lu, C. Lin, H. Jia, H. Wu, F. Cao, P. Ouyang, Polym. Test. 2020, 91, 106793.
- 6H. Al Salloum, J. Saunier, C. Aymes-Chodur, H. Barakat, N. Yagoubi, Int. J. Pharm. 2015, 496, 664.
- 7J. Chen, K. Li, Y. Wang, J. Huang, X. Nie, J. Jiang, Polymers 2017, 9, 640.
- 8Y. Xu, J. Jang, M. C. Gye, Environ. Pollut. 2022, 300, 118985.
- 9C. M. Shaha, R. S. Pandit, Ecotoxicology 2022, 31, 385.
- 10M. Park, I. Choi, S. Lee, S.-J. Hong, A. Kim, J. Shin, H.-C. Kang, Y.-W. Kim, J. Ind. Eng. Chem. 2020, 88, 148.
- 11M. W. Halloran, L. Danielczak, J. A. Nicell, R. L. Leask, M. Marić, A. C. S. Appl, Polym. Mater. 2022, 4, 3608.
- 12P. Jia, M. Zhang, L. Hu, G. Feng, C. Bo, Y. Zhou, ACS Sustain. Chem. Eng. 2015, 3, 2187.
- 13P. Jia, Y. Ma, F. Song, C. Liu, L. Hu, Y. Zhou, Mater. Today. Chem. 2021, 21, 100518.
- 14J. Chen, Y. Wang, J. Huang, K. Li, X. Nie, ACS Sustain. Chem. Eng. 2017, 6, 642.
- 15P. Jia, Y. Ma, H. Xia, M. Zheng, G. Feng, L. Hu, M. Zhang, Y. Zhou, ACS Sustain. Chem. Eng. 2018, 6, 13983.
- 16Y. Yang, J. Huang, R. Zhang, J. Zhu, Mater. Design. 2017, 126, 29.
- 17Y. Yang, Z. Xiong, L. Zhang, Z. Tang, R. Zhang, J. Zhu, Mater. Design. 2016, 91, 262.
- 18S. Lee, M. S. Park, J. Shin, Y.-W. Kim, Polym. Degrad. Stabil. 2018, 147, 1.
- 19M. Ali, Y. Lu, S. Ahmed, S. Khanal, S. Xu, ACS Omega 2020, 5, 17111.
- 20H. Chu, H. Li, X. Sun, Y. Zhang, J. Polym. Environ. 2022, 30, 3270.
- 21F. Hassouma, I. Mihai, L. Fetzer, T. Fouquet, J.-M. Raquez, A. Laachachi, H. Ibn, A. Ahrach, P. Dubois, Macromol. Mater. Eng. 2016, 301, 1267.
- 22P. Jia, L. Hu, M. Zhang, G. Feng, Y. Zhou, Eur. Polym. J. 2017, 87, 209.
- 23C. Zhang, H. Liang, D. Liang, Z. Lin, Q. Chen, P. Feng, Q. Wang, Angew. Chem. Int. Ed. Engl. 2021, 60, 4289.
- 24S. Mukherjee, M. Ghosh, J. Am. Oil Chem. Soc. 2019, 97, 187.
- 25H. Zhu, J. Yang, M. Wu, Q. Wu, J. Liu, J. Zhang, A. C. S. Sustain, Chem. Eng. 2021, 9, 15322.
- 26M. Li, S. Li, J. Xia, C. Ding, M. Wang, L. Xu, X. Yang, K. Huang, Mater. Design. 2017, 122, 366.
- 27G. E. Napolitano, Y. Ye, C. Cruz-Hernandez, J. Am. Oil Chem. Soc. 2018, 95, 583.
- 28S. Xu, M. E. Lamm, M. A. Rahman, X. Zhang, T. Zhu, Z. Zhao, C. Tang, Green Chem. 2018, 20, 1106.
- 29G. P. García-Inza, D. N. Castro, A. J. Hall, M. C. Rousseaux, Eur. J. Agron. 2016, 76, 138.
- 30A. Kammili, P. Yadav, Ind. Crop. Prod. 2022, 175, 114254.
- 31I. Omrani, A. Ahmadi, A. Farhadian, H. K. Shendi, N. Babanejad, M. R. Nabid, Polym. Test. 2016, 56, 237.
- 32D. Liu, Y. Shen, P. T. Wai, H. Agus, P. Zhang, P. Jiang, Z. Nie, G. Jiang, H. Zhao, M. Zhao, J. Appl. Polym. Sci. 2020, 138, 138.
- 33G. H. Hu, H. Li, L. F. Feng, Macromolecules 2002, 35, 8247.
- 34G. H. Hu, Y. Holl, M. Lambla, J. Polym. Sci., Part A: Polym. Chem. 1992, 30, 625.
- 35W. Y. Ji, T. T. Li, S. B. Cheng, L. F. Feng, X. P. Gu, C. L. Zhang, G. H. Hu, AIChE J. 2022, 68, e17835.
- 36H. Cartier, G. H. Hu, Polym. Eng. Sci. 1998, 38, 177.
- 37T. T. Li, F. Feng, X. P. Gu, C. L. Zhang, P. Wang, G. H. Hu, Ind. Eng. Chem. Res. 2021, 60, 2791.
- 38S. Sukanya, P. Aruna, J. Vinyl. Addit. Techn. 2021, 27, 599.