Self-Plasticization of PVC via click reaction of a monooctyl phthalate derivative

• Autorzy: Jia P. , Wang R. , Hu L. , Zhang M. , Zhou Y.

Identyfikatory

DOI

10.1515/pjct-2017-0042

• Języki publikacji: EN

Abstrakty

EN

Modified PVC (M-PVC) material with suppressed migration and low glass transition temperature was prepared via click reaction of a monooctyl phthalate derivative. Chemical structure and composition of M-PVC were characterized by FT-IR, 1H NMR and element analysis. Thermal stability, glass transition temperature and migration stability of M-PVC were studied with TGA, DSC and migration tests, respectively. The study showed that M-PVC exhibited poor thermal stability, and low glass transition temperature of 66.0°C. No migration was found in distilled water, 10% (v/v) ethanol, 30% (w/v)acetic acid and petroleum ether. The PVC material is expected to preparing PVC products in the areas with high migration resistance requirement.

Słowa kluczowe

EN

poly(vinyl chloride); plasticization; migration; TGA

• Wydawca: West Pomeranian University of Technology. Publishing House
• Czasopismo: Polish Journal of Chemical Technology
• Rocznik: 2017
• Tom: Vol. 19, nr 3
• Strony: 16--19
• Opis fizyczny: Bibliogr. 23 poz., rys.

Twórcy

autor

Jia P.

• Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry (CAF); National Engineering Lab for Biomass Chemical Utilization; Key Lab on Forest Chemical Engineering, State Forestry Administration; and Key Lab of Biomass Energy and Materials, Jiangsu Province, 16 Suojin North Road, Nanjing 210042, P.R. China

autor

Wang R.

• Nanjing Forestry University, College of Materials Science and Engineering, Nanjing 210037, China

autor

Hu L.

• Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry (CAF); National Engineering Lab for Biomass Chemical Utilization; Key Lab on Forest Chemical Engineering, State Forestry Administration; and Key Lab of Biomass Energy and Materials, Jiangsu Province, 16 Suojin North Road, Nanjing 210042, P.R. China
• Chinese Academy of Forest (CAF), Institute of New Technology of Forestry, Beijing 100091, P. R. China

autor

Zhang M.

• Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry (CAF); National Engineering Lab for Biomass Chemical Utilization; Key Lab on Forest Chemical Engineering, State Forestry Administration; and Key Lab of Biomass Energy and Materials, Jiangsu Province, 16 Suojin North Road, Nanjing 210042, P.R. China
• Chinese Academy of Forest (CAF), Institute of New Technology of Forestry, Beijing 100091, P. R. China

autor

Zhou Y.

• Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry (CAF); National Engineering Lab for Biomass Chemical Utilization; Key Lab on Forest Chemical Engineering, State Forestry Administration; and Key Lab of Biomass Energy and Materials, Jiangsu Province, 16 Suojin North Road, Nanjing 210042, P.R. China

Bibliografia

• 1. Jia, P., Zhang, M., Hu, L., Feng, G. & Zhou, Y. (2015). Synthesis of novel caged phosphate esters and their flame retardant effect on poly(vinyl chloride) blends. Chem. Lett. 44, 1220–1222. DOI: 10.1246/cl.150374.
• 2. Silva, M.A.D., Vieira, M.G.A., Maçumoto, A.C.G. & Beppu, M.M. (2011). Polyvinylchloride (PVC) and natural rubber films plasticized with a natural polymeric plasticizer obtained through polyesterification of rice fatty acid. Polym. Test. 30, 478–484. DOI: http://dx.doi.org/10.1016/j.polymertesting.2011.03.008.
• 3. Saeki, Y. & Emura, T. (2002). Technical progresses for PVC production. Prog. Polym. Sci. 27, 2055–2131. DOI: http://dx.doi.org/10.1016/S0079-6700(02)00039-4.
• 4. Bocqué, M., Voirin, C., Lapinte, V., Caillol, S. & Robin. J.J. (2016). Petro-based and bio-based plasticizers: Chemical structures to plasticizing properties. J. Polym. Sci. Part A: Polym. Chem. 54(1), n/a-n/a. DOI: 10.1002/pola.27917.
• 5 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 Chem. Eng. 3(9), 2187–2193. DOI:10.1021/acssuschemeng.5b00449.
• 6. Lindstrom, A. & Hakkarainen. M. (2007). Migration resistant polymeric plasticizer for poly(vinyl chloride). J. Appl. Polym. Sci. 104, 2458–2467. DOI: 10.1002/app.24777.
• 7. Latini, G., De, F.C. & Verrotti, A. (2004). Plasticizers, infant nutrition and reproductive health. Reprod. Toxicol. 19, 27–33. DOI: 10.1016/j.reprotox.2004.05.011.
• 8. Coltro, L., Pitta, J.B. & Madaleno. E. (2013). Performance evaluation of new plasticizers for stretch PVC films. Polym. Test. 2(2), 272–278. DOI: http://dx.doi.org/10.1016/j.polymertesting.2012.11.009.
• 9. Yu, B.Y., Chung, J.W. & Kwak. S.Y. (2008). Reduced migration from flexible poly(vinyl chloride) of a plasticizer containing beta-cyclodextrin derivative. Environ. Sci. Technol. 42(19), 7522–7527. DOI: 10.1021/es800895x.
• 10. Jia, P.Y., Zhang, M., Liu, C., Hu, L., Feng, G., Bo, C. & Zhou, Y. (2015). Effect of chlorinated phosphate ester based on castor oil on thermal degradation of poly (vinyl chloride) blends and its flame retardant mechanism as secondary plasticizer. RSC Adv. 5, 41169–41178. DOI: 10.1039/C5RA05784A.
• 11. Bueno-Ferrer, C., Garrigós, M.C. & Jiménez, A. (2010). Characterization and thermal stability of poly(vinyl chloride) plasticized with epoxidized soybean oil for food packaging. Polym. Degrad. Stab. 95, 2207–2212. DOI: 10.1016/j.polymdegradstab.2010.01.027.
• 12. 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). Pol. J. Chem. Technol. 18(1), 9–14. DOI: 10.1515/pjct-2016-0002.
• 13. Prabhakaran, K., Narayanan, A. & Pavithran, C. (2001). Cardanol as a dispersant plasticizer for an alumina/toluene tape casting slip. J. Eur. Cream Soc. 21, 2873–2878. DOI: http://dx.doi.org/10.1016/S0955-2219(01)00228-X.
• 14. Yang, X. & Hakkarainen, M. (2015). Migration resistant glucose esters as bioplasticizers for polylactide. J. Appl. Polym. Sci. 132(18). DOI: 10.1002/app.41928.
• 15. Schilling, S.U., Shah, N.H., Malick, A.W., Infeld, M.H. & McGinity, J.W. (2007). Citric acid as a solid-state plasticizer for Eudragit RS PO. J. Pharm. Pharmacol. 59, 1493–1500. DOI: 10.1211/jpp.59.11.0005.
• 16. Jia, P., Zhang, M., Hu, L., Feng, G., Bo, C., Liu, C. & Zhou, Y. (2015). Synthesis and application of phosphaphenanthrene groups-containing soybean-oil-based plasticizer. Ind. Crop. Prod. 76, 590–603. DOI: http://dx.doi.org/10.1016/j.indcrop.2015.07.034.
• 17. Jia, P., Zhang, M., Hu, L., Feng, G., Bo, C., Liu, C. & Zhou, Y. (2016). Green plasticizers derived from soybean oil for poly(vinyl chloride) as a renewable resource material. Korean J. Chem. Eng. 33(3), 1–8. DOI: 10.1007/s11814-015-0213-9.
• 18. Earla, A. & Braslau, R. (2014). Covalently Linked Plasticizers: Triazole Analogues of Phthalate Plasticizers Prepared by Mild Copper-Free “Click” Reactions with Azide-Functionalized PVC. Macromol. Rapid. Comm. 35, 666–671. DOI: 10.1002/marc.201300865.
• 19. Earla, A., Li, L., Costanzo, P. & Braslau, R. (2016). Phthalate plasticizers covalently linked to PVC via copper-free or copper catalyzed azide-alkyne cycloadditions. Polymer. DOI: 10.1016/j.polymer.2016.12.014.
• 20. Yang, P., Yan, J., Sun, H., Fan, H., Chen, Y., Wang, F. & Shi, B. (2015). Novel environmentally sustainable cardanol-based plasticizer covalently bound to PVC via click chemistry: synthesis and properties. Rsc. Adv. 5, 16980–16985. DOI: 10.1039/C4RA15527K.
• 21. Lee, K.W., Chung, J.W. & Kwak, S. (2016). Structurally enhanced self-plasticization of poly(vinyl chloride) via click grafting of hyperbranched polyglycerol. Macromol. Rapid. Comm. DOI: 10.1002/marc.201600533.
• 22. Navarro, R., Perrino, M.P., García, C., Elvira, C., Gallardo, A. & Reinecke, H. (2016) Highly Flexible PVC Materials without Plasticizer Migration As Obtained by Efficient One-Pot Procedure Using Trichlorotriazine Chemistry. Macromolecules DOI: 10.1021/acs.macromol.6b00214.
• 23. Hu, Z. & Di, C. (2003). Preparation of mono-2-ethlhexyl maleate and mono-2-ethylo-phthalate. Jiangsu Chem. Ind. 31, 38–39.

Uwagi

Opracowanie ze środków MNiSW w ramach umowy 812/P-DUN/2016 na działalność upowszechniającą naukę (zadania 2017).