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

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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.

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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 15:219–223

    Article  Google Scholar 

  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/s10853-017-0807-1

    Article  Google Scholar 

  3. Marcilla A, Garcia S, Garcia-Quesada JC (2008) Migrability of PVC plasticizers. Polym Test 27:221–233

    Article  Google Scholar 

  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 89:18–27

    Article  Google Scholar 

  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 126:29–36

    Article  Google Scholar 

  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 102:4835–4841

    Article  Google Scholar 

  7. Scientists R, Hygienists I (2012) Handbook of plasticizers. William Andrew, New York

    Google Scholar 

  8. Sears JK, Darby JR (1982) The technology of plasticizers. Wiley, New York

    Google Scholar 

  9. Sampson J, De KD (2011) DEHP-plasticised PVC: relevance to blood services. Transfus Med 21:73–83

    Article  Google Scholar 

  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 409:3309–3324

    Article  Google Scholar 

  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 74:206–212

    Article  Google Scholar 

  12. Wams TJ (1987) Diethylhexylphthalate as an environmental contaminant–a review. Sci Total Environ 66:1–61

    Article  Google Scholar 

  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 22:3620–3630

    Article  Google Scholar 

  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 79:71–82

    Article  Google Scholar 

  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/s10853-015-8844-0

    Article  Google Scholar 

  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/s10853-016-9838-2

    Article  Google Scholar 

  17. Wu D, Chang PR, Ma X (2011) Preparation and properties of layered double hydroxide–carboxymethylcellulose sodium/glycerol plasticized starch nanocomposites. Carbohydr Polym 86:877–882

    Article  Google Scholar 

  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/BF00544476

    Article  Google Scholar 

  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/s10853-009-3495-7

    Article  Google Scholar 

  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 107:3442–3450

    Article  Google Scholar 

  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 119:1600216–1600225

    Article  Google Scholar 

  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 89:668–673

    Article  Google Scholar 

  23. Chavan AP, Gogate PR (2015) Ultrasound assisted synthesis of epoxidized sunflower oil and application as plasticizer. J Ind Eng Chem 21:842–850

    Article  Google Scholar 

  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 43:377–379

    Article  Google Scholar 

  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 95:2169–2174

    Article  Google Scholar 

  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 14:53–64

    Article  Google Scholar 

  27. Lim H, Hoag SW (2013) Plasticizer effects on physical-mechanical properties of solvent cast soluplus films. AAPS PharmSciTech 14:903–910

    Article  Google Scholar 

  28. Iván B, Kelen T, Tüdös F (1989) The main elementary events of degradation and stabilization of PVC. Macromol Symp 29:59–72

    Article  Google Scholar 

  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 50:1565–1573

    Article  Google Scholar 

  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 50:208–214

    Article  Google Scholar 

  31. Jellinek HGH (1989) Degradation and stabilization of polymers. Elsevier, Dutch

    Google Scholar 

  32. Ayrey G, Man FP, Poller RC (1979) Mechanism of thermal stabilization of PVC by organotin compounds: scavenging of chlorine atoms. J Organomet Chem 173:171–174

    Article  Google Scholar 

  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 74:39–48

    Article  Google Scholar 

  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 53:8476–8483

    Article  Google Scholar 

  35. Coltro L, Pitta JB, Madaleno E (2013) Performance evaluation of new plasticizers for stretch PVC films. Polym Test 32:272–278

    Article  Google Scholar 

  36. Marcilla A, Garcia S, Garcia-Quesada JC (2008) Migrability of PVC plasticizers. Polym Test 27:221–233

    Article  Google Scholar 

  37. Kovačić T, Mrklić Ž (2002) The kinetic parameters for the evaporation of plasticizers from plasticized poly(vinyl chloride). Thermochim Acta 381:49–60

    Article  Google Scholar 

Download references

Acknowledgements

The authors are grateful for the financial support from the National “Twelfth Five-Year” Plan for Science & Technology Support (Grant Number: 2015BAD15B08) and the Key laboratory of biomass energy and materials of Jiangsu Province (Grant Number: JSBEM-S-201604).

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Authors and Affiliations

  1. Institute of Chemical Industry of Forestry Products, Chinese Academy of Forestry, Nanjing, 210042, Jiangsu, People’s Republic of China

    Jie Chen & Xiaoan Nie

  2. National Engineering Laboratory for Biomass Chemical Utilization, Nanjing, 210042, Jiangsu, People’s Republic of China

    Jie Chen & Xiaoan Nie

  3. Key Laboratory of Biomass Energy and Material, Nanjing, 210042, Jiangsu, People’s Republic of China

    Jie Chen & Xiaoan Nie

  4. USDA, ARS, National Center for Agricultural Utilization Research, Bio-Oils Research Unit, 1815 N University St, Peoria, IL, 61604, USA

    Zengshe Liu & Jianchun Jiang

Authors
  1. Jie Chen
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  2. Zengshe Liu
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  3. Xiaoan Nie
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  4. Jianchun Jiang
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Correspondence to Jie Chen or Xiaoan Nie.

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Zengshe Liu: Mention of trade names or commercial products in this publication is solely for the purpose of providing specific information and does not imply recommendation or endorsement by the U.S. Department of Agriculture. USDA is an equal opportunity provider and employer.

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Chen, J., Liu, Z., Nie, X. et al. Synthesis and application of a novel environmental C26 diglycidyl ester plasticizer based on castor oil for poly(vinyl chloride). J Mater Sci 53, 8909–8920 (2018). https://doi.org/10.1007/s10853-018-2206-7

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  • DOI: https://doi.org/10.1007/s10853-018-2206-7

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