Skip to main content
SpringerLink
Log in

Poly(vinyl chloride) plasticized with succinate esters: synthesis and characterization

  • Original Paper
  • Published:
Polymer Bulletin Aims and scope Submit manuscript

Abstract

Phthalates pose adverse health effects due to their propensity to leach and the most common, di(2-ethylhexyl) phthalate (DEHP) and di-n-octyl phthalate (DOP), are petroleum-based. Conversely, di-esters, succinates are biobased (produced from fermentation of biomass), biodegradable, and therefore potential sustainable replacements for phthalates. A series of succinates, di-octyl succinate (DOS), di-hexyl succinate (DHS), di-butyl succinate (DBS), and di-ethyl succinate (DES), were mixed with poly(vinyl chloride) (PVC). The interaction of the plasticizer ester carbonyl with PVC shows an average −5 cm−1 shift of the carbonyl absorbance peak energy. The glass transition temperatures (T g), were monitored by differential scanning calorimetry and dynamic mechanical analyses. The T gs of DOS and DHS plasticized PVC were significantly lower than DOP plasticized PVC at a lower percent mass. On the other hand, PVC plasticized with either DBS or DES exhibited a similar trend in lowering the T g as that of DOP plasticized PVC.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Wilson AS (1995) Plasticizers: principles and practice. The Institute of Materials, Great Britain

    Google Scholar 

  2. Gillum N, Karabekian Z, Swift LM, Brown RP, Kay MW, Sarvazyan N (2009) Clinically relevant concentrations of di(2-ethylhexyl) phthalate (DEHP) uncouple cardiac syncytium. Toxicol Appl Pharmacol 236:25–38

    Article  CAS  Google Scholar 

  3. Tickner JA, Schettler T, Guidotti T, McCally M, Rossi M (2001) Health risks posed by use of di-2-ethylhexyl phthalate (DEHP) in PVC medical devices: a critical review. Am J Ind Med 39:100–111

    Article  CAS  Google Scholar 

  4. Challener C (2006) Au naturel. In: Specialty Chemicals Magazine. DNP Green Technology. http://www.dnpworld.com/news/October_2006.Specialty_Chemicals_%20reprint.pdf. Accessed 18 May 2009

  5. McCoy M (2008) Converging pathways: chemical companies and environmentalists edge closer together in the pursuit of sustainability. C&EN 33:47–56

    Google Scholar 

  6. Rehberg CE, Dietz TJ, Meiss PE, Dixon MB (1952) Plasticizers from lactic esters and dibasic acids. Ind Eng Chem 44:2191–2195

    Article  CAS  Google Scholar 

  7. Ebert J (2007) The quest to commercialize biobased succinic acid. In: Biomass Magazine. http://biomassmagazine.com/article.jsp?article_id=1228. Accessed 18 May 2009

  8. Hamilton-Kemp T, Newman M, Collins R, Elgaali H, Yu K, Archbold D (2005) Production of the long-chain alcohols octanol, decanol, and dodecanol by Escherichia coli. Curr Microbiol 51:82–86

    Article  CAS  Google Scholar 

  9. Zubay G (1983) Biochemistry. Addison-Wesley Publishing Co, Reading, MA

    Google Scholar 

  10. Wickson EJ (1993) Handbook of PVC formulating. Wiley-Interscience, New York

    Google Scholar 

  11. Matthews G (1996) PVC: production, properties, and uses. The Institute of Materials, Great Britain

    Google Scholar 

  12. van Veersen GJ, Meulenberg AJ (1967) Relation between the chemical structure and the efficiency of plasticizers. Kunststoffe 57:561–566

    Google Scholar 

  13. McGee HL, Crimi JS, Schwartz PM (1962) Some physical properties of long-chained esters of dibasic acids. J Chem Eng Data 1:102–106

    Article  Google Scholar 

  14. Mark HF (2003) Encyclopedia of polymer science and technology, vol 3, 3rd edn. Wiley-Interscience, Hoboken, NJ

    Google Scholar 

  15. Iskandar M, Tran C, Robeson LM, McGrath JE (1983) Fourier transform infrared studies of poly(vinyl chloride) blends with ethylene co- and terpolymers. Polym Eng Sci 23:682–688

    Article  CAS  Google Scholar 

  16. Small PA (1953) Factors affecting the solubility of polymers. J Appl Chem 3:71–80

    Article  CAS  Google Scholar 

  17. Soong SY, Cohen RE, Boyce MC, Mulliken AD (2006) Rate-dependent deformation behavior of POSS-filled and plasticized poly(vinyl chloride). Macromol 39:2900–2908

    Article  CAS  Google Scholar 

  18. Elicegui A (1998) α and β relaxation processes in internally plasticized poly(vinyl chloride). J Non-Cryst Solids 235:623–627

    Article  Google Scholar 

  19. Kinjo N, Nakagawa T (1973) Antiplasticization in the slightly plasticized poly(vinyl chloride). Polym J 4:143–153

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors would like to acknowledge early project inputs from Prof. Kris Berglund of Lulea University and Michigan State University and Dr. Dilum Dunuwila from Diversified Natural Products Green Technology Inc. This work was supported by the Research Excellence Fund from Central Michigan University.

Author information

Authors and Affiliations

  1. Department of Chemistry, Central Michigan University, Mount Pleasant, MI, 48859, USA

    Amanda Stuart, Megan M. McCallum, Daming Fan, Dale J. LeCaptain, Choon Y. Lee & Dillip K. Mohanty

Authors
  1. Amanda Stuart
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Megan M. McCallum
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Daming Fan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Dale J. LeCaptain
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Choon Y. Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Dillip K. Mohanty
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Dale J. LeCaptain.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Stuart, A., McCallum, M.M., Fan, D. et al. Poly(vinyl chloride) plasticized with succinate esters: synthesis and characterization. Polym. Bull. 65, 589–598 (2010). https://doi.org/10.1007/s00289-010-0271-4

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00289-010-0271-4

Keywords

Search

Navigation