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

Open access

Abstract

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.

If the inline PDF is not rendering correctly, you can download the PDF file here.

  • 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.

Search
Journal information
Impact Factor


IMPACT FACTOR 2018: 0,975
5-year IMPACT FACTOR: 0,878

CiteScore 2018: 1

SCImago Journal Rank (SJR) 2018: 0.269
Source Normalized Impact per Paper (SNIP) 2018: 0.46

Cited By
Metrics
All Time Past Year Past 30 Days
Abstract Views 0 0 0
Full Text Views 1447 853 6
PDF Downloads 343 162 6