The Effects of Epoxidized Acrylated Castor Oil (EACO) on Soft Poly (vinyl chloride) Films as a Main Plasticizer

Song, Fei; Xia, Haoyu; Jia, Puyou; Zhang, Meng; Hu, Lihong; Zhou, Yonghong

doi:10.2478/pjct-2018-0048

Abstract

In this work, an environmentally friendly type plasticizer was introduced. The synthesis consisted of two steps. In the first step, castor oil (CO) was acrylated and then the acrylated castor oil (ACO) was epoxidized with the presence of formic acid and hydrogen peroxide in the second step. The epoxidized acrylated castor oil (EACO) was characterized by FTIR and ¹H-NMR techniques. The EACO was used as a main plasticizer to obtain plasticized PVC materials and compared with DOP. The results showed that EACO improved polyvinyl-chloride (PVC) plasticization performance and reduced Tg from 81.06°C to 1.40°C. Plasticized PVC materials with EACO showed similar mechanical properties and better thermal stability than DOP. EACO had better volatility stabilities, migration and solvent extraction in PVC than DOP. EACO can be used to replace DOP to prepare soft films.

References

1. Chen, J.X., Li, Y., Wang, J., Huang, K., Li, X. & Nie, J. Jiang. (2017). Synthesis and application of environmental soybean oil-based epoxidized glycidyl ester plasticizer for poly(vinyl chloride). European J. Lipid Sci. Technol. 119 (5). DOI: 10.1002/ejlt.201600216.10.1002/ejlt.201600216
Open DOI Search in Google Scholar Back to article
2. Bocqué, M., Voirin, C., Lapinte, V., Caillol, S. & Robin, J.. (2016). Petro-based and bio-based plasticizers: Chemical structures to plasticizing properties. J. Polym. Sci. Part B: Polymer Physics. 54 (1):11-33. DOI: 10.1002/pola.27917.10.1002/pola.27917
Open DOI Search in Google Scholar Back to article
3. Choi, W., Chung, J.W. & Kwak, S. (2014). Unentangled starshape poly(ε-caprolactone)s as phthalate-free PVC plasticizers designed for non-toxicity and improved migration resistance. ACS Applied Materials & Interfaces. 6 (14), 11118-11128. DOI: 10.1021/am500740v.10.1021/am500740v
Open DOI Search in Google Scholar Back to article
4. Ventrice, P., Ventrice, D., Russo, E. & De. Sarro., G. (2013). Phthalates: European regulation, chemistry, pharmacokinetic and related toxicity. Environ. Toxicol. Pharmacol. 36 (1):88-96. DOI: 10.1016/j.etap.2013.03.014.10.1016/j.etap.2013.03.014
Open DOI Search in Google Scholar Back to article
5. Gardner, S.T., Wood, A.T., Lester, R., Onkst, P.E., Burnham, N., Perygin, D.H. & Rayburn, J. (2016). Assessing differences in toxicity and teratogenicity of three phthalates, Diethyl phthalate, Di-n-propyl phthalate, and Di-n-butyl phthalate, using Xenopus laevis embryos. J. Toxicol. & Environ. Health. 79 (2):1-12. DOI: 10.1080/15287394.2015.1106994.10.1080/15287394.2015.1106994
Open DOI Search in Google Scholar Back to article
6. Chen, X., Xu, S., Tan, T., Lee, S.T., Cheng, S.H., Lee, F.W.F., Xu, S.J.L. & Ho, K.C. (2014). Toxicity and estrogenic endocrine disrupting activity of phthalates and their mixtures. Int. J. Environ. Res. Public Health. 11 (3), 3156-3168. DOI: 10.3390/ijerph110303156.10.3390/ijerph110303156
Open DOI Search in Google Scholar Back to article
7. Li, J. & Ko, Y.C. (2012). Plasticizer incident and its health effects in Taiwan. The Kaohsiung journal of medical sciences. 28 (7), S17-S21. DOI: 10.1016/j.kjms.2012.05.005.10.1016/j.kjms.2012.05.005
Open DOI Search in Google Scholar Back to article
8. Yao, L., Chen, Q., Xu, W., Ye, Z., Shen, Z. & Chen, M.. (2017). Preparation of cardanol based epoxy plasticizer by click chemistry and its action on poly(vinyl chloride). J. Appl. Polym. Sci. 134 (23), 44890. DOI: 10.1002/APP.44890.10.1002/app.44890
Search in Google Scholar Back to article
9. Jia, P., Zhang, M., Hu, L. & Zhou, Y. (2016). Green plasticizers derived from soybean oil for poly(vinyl chloride) as a renewable resource material. Korean J. Chem. Engineer. 33 (3), 1080-1087. DOI: 10.1007/s11814-015-0213-9.10.1007/s11814-015-0213-9
Open DOI Search in Google Scholar Back to article
10. Feng, G., Yun, H., Pu-you, J., Ma, Y. & Yong-hong, Z. (2015). Influence of a nitrogen-containing oil-based plasticizer on mechanical, thermal stability and fire performance of plasticized poly(vinyl chloride) and study of its mechanism of flame retardancy with Py-GC/MS. Industrial Crops and Products. 77, 883-894. DOI: 10.1016/ j.indcrop.2015.09.032.10.1016/j.indcrop.2015.09.032
Search in Google Scholar Back to article
11. Qiu, J.F., Zhang, M.Q., Rong, M.Z., Wu, S.P. & Karger- -Kocsis, A.J. (2013). Rigid bio-foam plastics with intrinsic flame retardancy derived from soybean oil. J. Mater. Chem. A, 1(7), 2533-2542. DOI: 10.1039/C2TA01404A.10.1039/201404
Open DOI Search in Google Scholar Back to article
12. Jia, P., Zhang, M., Hu, L., Zhou, J., Feng, G. & Zhou, Y. (2015). Thermal degradation behavior and flame retardant mechanism of poly(vinyl chloride) plasticized with a soybean-oil-based plasticizer containing phosphaphenanthrene groups. Polymer Degradation and Stability. 121, 292-302. DOI: 10.1016/j.polymdegradstab. 2015.09.020.10.1016/j.polymdegradstab.2015.09.020
Open DOI Search in Google Scholar Back to article
13. Li, M., Li, S., Xia, J., Ding, C., Wang, M., Xu, L., Yang, X. & Huang, K. (2017). Tung oil based plasticizer and auxiliary stabilizer for poly(vinyl chloride). Materials & Design. 122, 366-375. DOI: 10.1016/j.matdes.2017.03.025.10.1016/j.matdes.2017.03.025
Open DOI Search in Google Scholar Back to article
14. Chen, J., Wang, Y., Huang, J., Li, K. & Nie, X. (2018). Synthesis of tung oil based triglycidyl ester plasticizer and its effects on poly(vinyl chloride) soft films. ACS Sustainable Chemistry & Engineering. 6 (1), 642-651. DOI: 10.1021/acssuschemeng.7b02989.10.1021/acssuschemeng.7b02989
Open DOI Search in Google Scholar Back to article
15. Jia, P., Hu, L., Yang, X., Zhang, M., Shang, Q., Zhou, A.Y. (2017). Internally plasticized PVC materials via covalent attachment of aminated tung oil methyl ester. RSC Advances. 7 (48), 30101-30108. DOI: 10.1039/c7ra04386d.10.1039/c7ra04386d
Open DOI Search in Google Scholar Back to article
16. Ang, D.T., Khong, Y.K. & Gan, S.N. (2016). Palm oil- -based compound as environmentally friendly plasticizer for poly(vinyl chloride). J. Vinyl and Additive Technol. 22 (1):80-87. DOI: 10.1002/vnl.21434.10.1002/vnl.21434
Open DOI Search in Google Scholar Back to article
17. Jia, P., Zhang, M., Hu, L. & Zhou, Y. (2016). A novel biobased polyester plasticizer prepared from palm oil and its plasticizing effect on poly (vinyl chloride). Polish J. Chemical Technol. 18 (1):9-14. DOI: 10.1515/pjct-2016-0002.10.1515/pjct-2016-0002
Open DOI Search in Google Scholar Back to article
18. Carbonell-Verdu, A., Garcia-Sanoguera, D., Jorda-Vilaplana, A., Sanchez-Nacher, L. & Balart, R. (2016). A new biobased plasticizer for poly(vinyl chloride) based on epoxidized cottonseed oil. J. Appl. Polym. Sci. 133 (27), 43642. DOI: 10.1002/APP.43642.10.1002/app.43642
Search in Google Scholar Back to article
19. Carbonell-Verdu, A., Samper, M.D., Garcia-Garcia, D., Sanchez-Nacher, L. & Balart, R. (2017). Plasticization effect of epoxidized cottonseed oil (ECSO) on poly(lactic acid). Industrial Crops and Products. 104, 278-286. DOI: 10.1016/j.indcrop.2017.04.050.10.1016/j.indcrop.2017.04.050
Open DOI Search in Google Scholar Back to article
20. Faria-Machado, A.F., Silva, M.A.D., Vieira, M.G.A., Beppu, M.M. (2013). Epoxidation of modified natural plasticizer obtained from rice fatty acids and application on polyvinylchloride films. J. Appl. Polymer Sci. 127 (5), 3543-3549. DOI: 10.1002/app.37671.10.1002/app.37671
Open DOI Search in Google Scholar Back to article
21. Nihul, PG., Mhaske, S.T., Shertukde, V.V. (2014). Epoxidized rice bran oil (ERBO) as a plasticizer for poly(vinyl chloride) (PVC). Iranian Polymer J. 23 (8), 599-608. DOI: 10.1007/s13726-014-0254-7.10.1007/s13726-014-0254-7
Search in Google Scholar Back to article
22. Ogunniyi, D.S. (2006). Castor oil: a vital industrial raw material. Bioresource technology. 97 (9), 1086-91. DOI: i:10.1016/j.biortech.2005.03.028.10.1016/j.biortech.2005.03.028
Open DOI Search in Google Scholar Back to article
23. Raju, P., Nandanan, V. & Sunil, K.N.K. (2007). A Study on the Use of Castor Oil as Plasticizer in Natural Rubber Compounds. Progress in rubber, plastics and recycling technology. 23(3), 169-180.10.1177/147776060702300302
Search in Google Scholar Back to article
24. Tsujimoto, T., Haza, Y., Yin, Y. & Uyama, H. (2014). Synthesis of branched poly(lactic acid) bearing a castor oil core and its plasticization effect on poly(lactic acid). Polymer J. 43 (4), 425-430. DOI: 10.1038/pj.2011.3.10.1038/pj.2011.3
Open DOI Search in Google Scholar Back to article
25. Mehta, B., Kathalewar, M. & Sabnis, A.. (2014). Diester based on castor oil fatty acid as plasticizer for poly(vinyl chloride). J. Appl. Polymer Sci. 131 (11), 2928-2935. DOI: 10.1002/APP.40354.10.1002/APP.40354
Open DOI Search in Google Scholar Back to article
26. Jia, P., Bo, C., Zhang, L., Hu, L., Zhang, M. & Zhou, Y. (2015). Synthesis of castor oil based plasticizers containing flame retarded group and their application in poly (vinyl chloride) as secondary plasticizer. J. Industrial Engineer. Chem. 28, 217-224. DOI:10.1016/j.jiec.2015.02.017.10.1016/j.jiec.2015.02.017
Open DOI Search in Google Scholar Back to article
27. Jia, P., Hu, L., Zhang, M. & Zhou, Y. (2016). TG-FTIR and TG-MS analysis applied to study the flame retardancy of PVC-castor oil-based chlorinated phosphate ester blends. J. Thermal Anal. Calorim. 124(3), 1331-1339. DOI: 10.1007/s10973-015-5199-3.10.1007/s10973-015-5199-3
Open DOI Search in Google Scholar Back to article
28. Jia, P., Hu, L., Zhang, M., Feng, G. & Zhou, Y. (2017). Phosphorus containing castor oil based derivatives: Potential non-migratory flame retardant plasticizer. European Polymer J. 87, 209-220. DOI: 10.1016/j.eurpoly mj.2016.12.023.10.1016/j.eurpolymj.2016.12.023
Open DOI Search in Google Scholar Back to article
29. Feng, G., Jia, P., Zhang, L., Hu, L., Zhang, M. & Zhou, Y. (2015). Synthesis of a novel phosphorus-containing plasticizer based on castor oil and its application for flame retardancy of polyvinyl chloride. Korean J. Chem. Engineer. 32(6), 1201-1206. DOI: 10.1007/s11814-014-0288-8.10.1007/s11814-014-0288-8
Open DOI Search in Google Scholar Back to article
30. Jia, P., Zhang, M., Hu, L., Feng, G., Bo, C. & Zhou, Y. (2015). Synthesis and application of environmental castor oil based polyol ester plasticizers for poly (vinyl chloride). ACS Sustainable Chemistry & Engineering, 3(9), 2187-2193. DOI: 10.1021/acssuschemeng.5b00449.10.1021/acssuschemeng.5b00449
Open DOI Search in Google Scholar Back to article
31. Esen, H. & Çayli, G. (2016). Epoxidation and polymerization of acrylated castor oil. European J. Lipid Sci. Technol. 118(6), 959-966. DOI: 10.1002/ejlt.201500132.10.1002/ejlt.201500132
Open DOI Search in Google Scholar Back to article
32. Çayli, G., Gürbüz, D. & Çınarli, A. (2018). Characterization and Polymerization of Epoxidized Methacrylated Castor Oil. European J. Lipid Sci. Technol. DOI: 10.1002/ejlt.201700189.10.1002/ejlt.201700189
Open DOI Search in Google Scholar Back to article
33. Şahin, Y.M., Çaylı, G., Çavuşoğlu, J., Tekay, E. & Şen. S. (2016). Cross-linkable epoxidized maleinated castor oil: a renewable resin alternative to unsaturated polyesters. Int. J. Polymer Sci. DOI: 10.1155/2016/5781035.10.1155/2016/5781035
Open DOI Search in Google Scholar Back to article
34. Müller, R. & Wilke, G. (2014). Synthesis and radiation curing of acrylated castor oil glycerides. J. Coatings Technol. Res. 11(6), 873-882. DOI: 10.1007/s11998-014-9596-5.10.1007/s11998-014-9596-5
Open DOI Search in Google Scholar Back to article
35. Shibata, M. & Obara, S. (2012). Photo-cured organic- -inorganic hybrid composites of acrylated castor oil and methacrylate- substituted polysilsesquioxane. J. Appl. Polymer Sci. 126(S2). DOI: 10.1002/app.36582.10.1002/app.36582
Open DOI Search in Google Scholar Back to article
36. Wang, M., Song, X., Jiang, J., Xia, J. & Li, M. (2017). Binary amide-containing tung-oil-based Ca/Zn stabilizers: effects on thermal stability and plasticization performance of poly(vinyl chloride) and mechanism of thermal stabilization. Polymer Degradation and Stability. 143, 106-117. DOI: 10.1016/j.polymdegradstab.2017.06.022.10.1016/j.polymdegradstab.2017.06.022
Open DOI Search in Google Scholar Back to article
37. Chen, J., Nie, X. & Jiang, J. (2018). Synthesis and application of a novel cardanol-based plasticizer as secondary or main plasticizer for poly (vinyl chloride). Polymer International. 67(3), 269-275. DOI: 10.1002/pi.5503.10.1002/pi.5503
Open DOI Search in Google Scholar Back to article
38. Chen, J., Liu, Z., Nie, X. & Jiang, J. (2018). Synthesis and application of a novel environmental C26 diglycidyl ester plasticizer based on castor oil for poly (vinyl chloride). J. Mater. Sci. 53(12), 8909-8920. DOI: 10.1007/s10853-018-2206-7.10.1007/s10853-018-2206-7
Open DOI Search in Google Scholar Back to article
39. Chandola, M. & Marathe, S. (2008). A QSPR for the plasticization efficiency of polyvinylchloride plasticizers. J. Molec. Graphics and Modelling. 26(5), 824-828. DOI: 10.1016/j.jmgm.2007.04.008.10.1016/j.jmgm.2007.04.008
Open DOI Search in Google Scholar Back to article
40. Haryono, A., Triwulandari, E. & Jiang, P. (2017). Interaction between vegetable oil based plasticizer molecules and polyvinyl chloride, and their plasticization effect. AIP Conference Proceedings. 1803(1), 020045. DOI: 10.1063/1.4973172.10.1063/1.4973172
Open DOI Search in Google Scholar Back to article
41. Yang, Y., Huang, J., Zhang, R. & Zhu, J. (2017). Designing bio-based plasticizers: Effect of alkyl chain length on plasticization properties of isosorbide diesters in PVC blends. Materials & Design. 126, 29-36. DOI:10.1016/j.matdes.2017.04.005.10.1016/j.matdes.2017.04.005
Open DOI Search in Google Scholar Back to article

The Effects of Epoxidized Acrylated Castor Oil (EACO) on Soft Poly (vinyl chloride) Films as a Main Plasticizer

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