journal article·2018-06

Synthesis and application of a novel environmental C26 diglycidyl ester plasticizer based on castor oil for poly(vinyl chloride)

Jie Chen, Zengshe Liu, Xiaoan Nie, Jianchun Jiang

Journal of Materials Science· Volume 53· Issue 12
Publisher page

Abstract

A castor oil-derived diglycidyl ester plasticizer (C26-DGE) was prepared and incorporated into poly(vinyl chloride) (PVC) for the first time. The chemical structure of the product was characterized by Fourier transform infrared spectroscopy (FTIR), proton nuclear magnetic resonance (1H-NMR), and carbon-13 nuclear magnetic resonance (13C-NMR). The plasticizing effects of C26-DGE as a primary or secondary plasticizer for the commercial plasticizer dioctyl phthalate (DOP) were studied. The mechanical properties, thermal stability, and migration stabilities of PVC films were investigated using dynamic mechanical analysis, thermogravimetric analysis (TGA), TGA-FTIR analysis, and PVC film surface analysis. Tensile, volatility, and extraction tests were also done. The castor oil-based plasticizer was found to endow the PVC matrix with enhanced compatibility and flexibility. With partially or completely substituted DOP, C26-DGE significantly increased the thermal stability of PVC blends. Furthermore, the volatility and extraction resistance of the novel plasticizers were generally superior to those of DOP. The interaction between the C26-DGE and PVC molecules and the thermal degradation process of PVC blends were also investigated.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Polymer Science and PVC · Extraction and Separation Processes · Polymer crystallization and properties

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References (37)

Show source-provided references
1. Daniels PH (2009) A brief overview of theories of PVC plasticization and methods used to evaluate PVC-plasticizer interaction. J Vinyl Addit Technol 15:219–22310.1002/vnl.20211 ↗
2. Roy KJ, Anjali TV, Sujith A (2017) Asymmetric membranes based on poly(vinyl chloride): effect of molecular weight of additive and solvent power on the morphology and performance. J Mater Sci 52:5708–5725. https://doi.org/10.1007/s10853-017-0807-110.1007/s10853-017-0807-1 ↗
3. Marcilla A, Garcia S, Garcia-Quesada JC (2008) Migrability of PVC plasticizers. Polym Test 27:221–23310.1016/j.polymertesting.2007.10.007 ↗
4. Erythropel HC, Shipley S, Börmann A, Nicell JA, Maric M, Leask RL (2016) Designing green plasticizers: Influence of molecule geometry and alkyl chain length on the plasticizing effectiveness of diester plasticizers in PVC blends. Polymer 89:18–2710.1016/j.polymer.2016.02.031 ↗
5. 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. Mater Des 126:29–3610.1016/j.matdes.2017.04.005 ↗
6. Alexander M, Thachil ET (2006) A comparative study of cardanol and aromatic oil as plasticizers for carbon-black-filled natural rubber. J Appl Polym Sci 102:4835–484110.1002/app.24811 ↗
7. Scientists R, Hygienists I (2012) Handbook of plasticizers. William Andrew, New York
8. Sears JK, Darby JR (1982) The technology of plasticizers. Wiley, New York
9. Sampson J, De KD (2011) DEHP-plasticised PVC: relevance to blood services. Transfus Med 21:73–8310.1111/j.1365-3148.2010.01056.x ↗
10. Lithner D, Larsson A, Dave G (2011) Environmental and health hazard ranking and assessment of plastic polymers based on chemical composition. Sci Total Environ 409:3309–332410.1016/j.scitotenv.2011.04.038 ↗
11. Drake PL, Rojas M, Reh CM, Mueller CA, Jenkins FM (2001) Occupational exposure to airborne mercury during gold mining operations near El Callao, Venezuela. Int Arch Occ Env Hea 74:206–21210.1007/s004200000206 ↗
12. Wams TJ (1987) Diethylhexylphthalate as an environmental contaminant–a review. Sci Total Environ 66:1–6110.1016/0048-9697(87)90072-6 ↗
13. Wang WL, Wu QY, Wang C, He T, Hu HY (2015) Health risk assessment of phthalate esters (PAEs) in drinking water sources of China. Environ Sci Pollut Res 22:3620–363010.1007/s11356-014-3615-z ↗
14. Gardner ST, Wood AT, Lester R, Onkst PE, Burnham N, Perygin DH, 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 A 79:71–8210.1080/15287394.2015.1106994 ↗
15. Koziara BT, Nijmeijer K, Benes NE (2015) Optical anisotropy, molecular orientations, and internal stresses in thin sulfonated poly(ether ether ketone) films. J Mater Sci 50:3031–3040. https://doi.org/10.1007/s10853-015-8844-010.1007/s10853-015-8844-0 ↗
16. Ferri JM, Samper MD, García-Sanoguera D, Reig MJ, Fenollar O, Balart R (2016) Plasticizing effect of biobased epoxidized fatty acid esters on mechanical and thermal properties of poly(lactic acid). J Mater Sci 51:5356–5366. https://doi.org/10.1007/s10853-016-9838-210.1007/s10853-016-9838-2 ↗
17. Wu D, Chang PR, Ma X (2011) Preparation and properties of layered double hydroxide–carboxymethylcellulose sodium/glycerol plasticized starch nanocomposites. Carbohydr Polym 86:877–88210.1016/j.carbpol.2011.05.030 ↗
18. Ollett AL, Parker R, Smith AC (1991) Deformation and fracture behaviour of wheat starch plasticized with glucose and water. J Mater Sci 26:1351–1356. https://doi.org/10.1007/BF0054447610.1007/BF00544476 ↗
19. Fenollar O, Sanchez-Nacher L, Garcia-Sanoguera D, López J, Balart R (2009) The effect of the curing time and temperature on final properties of flexible PVC with an epoxidized fatty acid ester as natural-based plasticizer. J Mater Sci 44:3702–3711. https://doi.org/10.1007/s10853-009-3495-710.1007/s10853-009-3495-7 ↗
20. Bouchareb B, Benaniba MT (2010) Effects of epoxidized sunflower oil on the mechanical and dynamical analysis of the plasticized poly(vinyl chloride). J Appl Polym Sci 107:3442–345010.1002/app.27458 ↗
21. Chen J, Li X, Wang Y, Huang J, Li K, Nie X, Jiang J (2016) Synthesis and application of environmental soybean oil based epoxidized glycidyl ester plasticizer for poly(vinyl chloride). Eur J Lipid Sci Technol 119:1600216–160022510.1002/ejlt.201600216 ↗
22. Joseph R, Alex R, Vinod VS, Premalatha CK, Kuriakose B (2003) Studies on epoxidized rubber seed oil as plasticizer for acrylonitrile butadiene rubber. J Appl Polym Sci 89:668–67310.1002/app.12037 ↗
23. Chavan AP, Gogate PR (2015) Ultrasound assisted synthesis of epoxidized sunflower oil and application as plasticizer. J Ind Eng Chem 21:842–85010.1016/j.jiec.2014.04.021 ↗
24. Krewson CF, Riser GR, Scott WE (1966) Euphorbia and Vernonia seed oil products as plasticizer-stabilizers for polyvinyl chloride. J Am Oil Chem Soc 43:377–37910.1007/BF02646792 ↗
25. Greco A, Brunetti D, Renna G, Mele G, Maffezzoli A (2010) Plasticizer for poly(vinyl chloride) from cardanol as a renewable resource material. Polym Degrad Stab 95:2169–217410.1016/j.polymdegradstab.2010.06.001 ↗
26. Sharma AK, Mahanwar PA (2010) Effect of particle size of fly ash on recycled poly (ethylene terephthalate)/fly ash composites. Int J Plast Tech 14:53–6410.1007/s12588-010-0006-2 ↗
27. Lim H, Hoag SW (2013) Plasticizer effects on physical-mechanical properties of solvent cast soluplus films. AAPS PharmSciTech 14:903–91010.1208/s12249-013-9971-z ↗
28. Iván B, Kelen T, Tüdös F (1989) The main elementary events of degradation and stabilization of PVC. Macromol Symp 29:59–7210.1002/masy.19890290106 ↗
29. Jiménez A, Berenguer V, López J, Sánchez A (2010) Thermal degradation study of poly(vinyl chloride): kinetic analysis of thermogravimetric data. J Appl Polym Sci 50:1565–157310.1002/app.1993.070500910 ↗
30. Szarka G, Iván B (2013) Thermal properties, degradation and stability of poly(vinyl chloride) predegraded thermooxidatively in the presence of dioctyl phthalate plasticizer. J Macromol Sci A 50:208–21410.1080/10601325.2013.742804 ↗
31. Jellinek HGH (1989) Degradation and stabilization of polymers. Elsevier, Dutch
32. Ayrey G, Man FP, Poller RC (1979) Mechanism of thermal stabilization of PVC by organotin compounds: scavenging of chlorine atoms. J Organomet Chem 173:171–17410.1016/S0022-328X(00)81286-3 ↗
33. Botelho G, Queirós A, Liberal S, Gijsman P (2001) Studies on thermal and thermo-oxidative degradation of poly(ethylene terephthalate) and poly(butylene terephthalate). Polym Degrad Stab 74:39–4810.1016/S0141-3910(01)00088-X ↗
34. Qu H, Xin L, Xu J, Ma H, Jiao Y, Xie J (2014) Investigation on thermal degradation of poly(1,4-butylene terephthalate) filled with aluminum hypophosphite and trimer by thermogravimetric analysis-Fourier transform infrared spectroscopy and thermogravimetric analysis-mass spectrometry. Ind Eng Chem Res 53:8476–848310.1021/ie404297r ↗
35. Coltro L, Pitta JB, Madaleno E (2013) Performance evaluation of new plasticizers for stretch PVC films. Polym Test 32:272–27810.1016/j.polymertesting.2012.11.009 ↗
36. Marcilla A, Garcia S, Garcia-Quesada JC (2008) Migrability of PVC plasticizers. Polym Test 27:221–23310.1016/j.polymertesting.2007.10.007 ↗
37. Kovačić T, Mrklić Ž (2002) The kinetic parameters for the evaporation of plasticizers from plasticized poly(vinyl chloride). Thermochim Acta 381:49–6010.1016/S0040-6031(01)00643-8 ↗