Skip to main content
SpringerLink
Log in

Novel reactive polymerizable nonyl phenol ethoxylate surfactants as emulsifier in non-aqueous emulsion polymerization

  • Synthesis
  • Published:
Polymer Science Series B Aims and scope Submit manuscript

Abstract

In this work, new series of modified nonionic polymerizable nonyl phenol ethoxylates (NPEs) were synthesized as organic solvent-soluble surfactants. The nonyl, phenyl and propenyl groups were acted as solvophilic segment. The modified polyoxyethylene, maleate chains were behaved as solvophobic segment. The new bifunctional surfmers were prepared by reacting polyoxyethylene 4-nonyl-2-propylenephenol nonionic reactive surfactant with maleic anhydride followed by esterification with poly(ethylene glycol). The chemical structure of the prepared surfactants was determined by 13C and 1H NMR analyses. The surface activities of these surfactants were determined in organic solvents including formamide, toluene and aqueous water solvent from surface tension measurements. The relationship between the surface activity and molecular structure of the organic solvent-soluble polymerizable NPE surfactants as well as the type and structure of organic solvents were discussed. The results showed that the prepared polymerizable NPE surfactants have been reduced the surface tension of both polar and non-polar organic solvents. Surface parameters such as surface excess concentration (Γmax), the area per molecule at interface (A min) and the effectiveness of surface tension reduction were determined from the adsorption isotherms of the prepared surfactants. The prepared polymerizable surfactant used to prepare crosslinked N-isopropylacrylamide (NIPAAm) and 2-acrylamido-2-methylpropane sulfonic acid (AMPS) copolymer microgel based on nonaqueous emulsion copolymerization.

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

Similar content being viewed by others

References

  1. A. M. Warhurst, An Environmental Assessment of Alkylphenol Ethoxylates and Alkylphenols (Friends of the Earth Scotland, Edinburgh, 1995), pp. 75–105.

    Google Scholar 

  2. S. S. Talmage, Environmental and Human Safety of Major Surfactants. Alcohol Ethoxylates and Alkylphenol Ethoxylates (Lewis Publishers, Boca Raton, Florida, 1994), pp. 115–125.

    Google Scholar 

  3. C. G. Naylor, J. B. Williams, P. T. Varineau, and D. A. Webb, “Nonylphenol ethoxylates in an industrial river” in Proceedings of 4th World Surfactants Congress, Barcelona, Spain, 1996, pp. 378–391.

    Google Scholar 

  4. A. Soares, B. Guieysse, B. Jefferson, E. Cartmell, and J. N. Lester, Environ. Int. 34, 1033 (2008).

    Article  CAS  Google Scholar 

  5. B. W. Green and D. P. J. Sheetz, Colloid Interface Sci. 32, 96 (1970).

    Article  Google Scholar 

  6. B. W. Green and F. L. Saunders, J. Colloid Interface Sci. 33, 393 (1970).

    Article  Google Scholar 

  7. S. L. Tsaur and R. B. J. Fitch, Colloid Interface Sci. 115, 450 (1987).

    Article  CAS  Google Scholar 

  8. S. A. Chen and H. S. Chang, J. Polym. Sci., Part A: Polym. Chem. 23, 2615 (1985).

    CAS  Google Scholar 

  9. Y. Morozumi and Y. Saito, Fuels 24, 1854 (2010).

    Article  CAS  Google Scholar 

  10. A. M. Fernandez, U. Held, A. Willing, and W. H. Breuer, Prog. Org. Coat. 53, 246 (2005).

    Article  CAS  Google Scholar 

  11. L. N. Butler, C. M. Fellows, and R. G. Gilbert, Prog. Org. Coat. 53, 112 (2005).

    Article  CAS  Google Scholar 

  12. H. Gutmann and A. S. Kertes, J. Colloid Interface Sci. 51, 406 (1975).

    Article  CAS  Google Scholar 

  13. G.-G. Ying, Environ. Int. 32, 417 (2006).

    Article  CAS  Google Scholar 

  14. E. Calvoa, R. Bravoa, A. Amigoa, and J. Gracia-Fadrique, Fluid Phase Equilib. 282, 14 (2009).

    Article  Google Scholar 

  15. M. Li and K. Matyjaszewski, Macromolecules 36, 6028 (2003).

    Article  CAS  Google Scholar 

  16. M. Dreja, W. Pyckhout-Hintzen, and B. Tieke, Macromolecules 31, 272 (1998).

    Article  CAS  Google Scholar 

  17. W. R. Palani-Raj, M. Sasthav, and H. M. Cheung, Langmuir 8, 1931 (1992).

    Article  Google Scholar 

  18. T. D. Li, C. H. Chew, S. C. Ng, L. M. Gan, W. K. Teo, J. Y. Gu, and G. Y. Zhang, J. Macromol. Sci. Pure Appl. Chem. A32, 969 (1995).

    Article  CAS  Google Scholar 

  19. L. M. Gan, T. D. Li. C. H. Chew, W. K. Teo, and L. H. Gan, Langmuir 11, 3316 (1995).

    Article  CAS  Google Scholar 

  20. A. Hammouda and M.-P. Pileni, Langmuir 11, 3656 (1995).

    Article  CAS  Google Scholar 

  21. M. Dreja and B. Tieke, Macromol. Rapid Commun. 17, 825 (1996).

    Article  CAS  Google Scholar 

  22. K. Landfester, N. Bechthold, F. Tiarks, and M. Antonietti, Macromolecules 32, 5222 (1999).

    Article  CAS  Google Scholar 

  23. X. J. Xu, H. L. Goh, K. S. Siow, and L. M. Gan, Langmuir 17, 6077 (2001).

    Article  CAS  Google Scholar 

  24. A. Guyot and K. Tauer, Adv. Polym. Sci. 111, 43 (1994).

    Article  CAS  Google Scholar 

  25. F. Candau and R. Zana, in Polymeric Materials Encyclopedia, Ed. by J. C. Salamone (CRC Press, Boca Ration, 1996), p. 4287.

  26. K. M. Lusvardi, K. V. Schubert, and E. W. Kaler, Ber Bunsen-Ges. Phys. Chem. 100, 373 (1996).

    Article  CAS  Google Scholar 

  27. K. Landfester, M. Willert, and M. Antonietti, Macromolecules 33, 2370 (2000).

    Article  CAS  Google Scholar 

  28. L.-I. Atanase and G. Riess, Polym. Int. 60, 1563 (2011).

    Article  CAS  Google Scholar 

  29. T. Tadros, Adv. Colloid Interface Sci. 147–148, 281 (2009).

    Article  Google Scholar 

  30. M. R. Thompson, C. Tzoganakis, and G. L. Rempel, J. Polym. Sci., Part A: Polym. Chem. 36, 2371 (1998).

    Article  CAS  Google Scholar 

  31. A. M. Al-Sabagh and A. M. Atta, J. Chem. Technol. Biotechnol. 74, 1075 (1999).

    Article  CAS  Google Scholar 

  32. V. Annadanam, S. Sainath, M. Isokawa, M. Suzuki, S. Ishii, S. Matsuura, N. Nagai, and T. Fujita, Macromolecules 42, 4356 (2009).

    Article  Google Scholar 

  33. A. Tomlinson, T. N. Danks, and D. M. Heyes, Langmuir 13, 5881 (1997).

    Article  CAS  Google Scholar 

  34. T. E. Sandovala, L. J. Espinozab, I. A. Guerrac, A. F. Olead, and M. P. Garate, Colloids Surf. A 398, 17 (2012).

    Article  Google Scholar 

  35. M. K. Bernett and W. A. Zisman, J. Phys. Chem. 66, 1207 (1962).

    Article  CAS  Google Scholar 

  36. A. M. Atta, Polym. Int. 56, 984 (2007).

    Article  CAS  Google Scholar 

  37. A. M. Atta, M. E. Abdel-Rauf, N. E. Maysour, A. M. Abdul-Rahiem, and A. A. Abdel-Azim, J. Polym. Res. 13, 39 (2006).

    Article  CAS  Google Scholar 

  38. A.M. Atta, H. I. Al-Shafy, and Z. M. Mohamed, Polym. Adv. Technol. 22, 1879 (2011).

    Article  CAS  Google Scholar 

  39. M. J. Rosen, Surfactants and Interfacial Phenomena (John Wiley, New York, 1985), pp. 15–55.

    Google Scholar 

  40. J. A. Garate, M. A. Valenzuela, M. P. Garate, and A. F. Olea, J. Surf. Deterg. 12, 231 (2009).

    Article  CAS  Google Scholar 

  41. X. J. Xu, H. L. Goh, K. S. Siow, and L. M. Gan, Langmuir 17, 6077 (2001).

    Article  CAS  Google Scholar 

  42. B. P. Binks, P. D. I. Fletcher, and S. N. Kotsev, Langmuir 13, 6669 (1997).

    Article  CAS  Google Scholar 

  43. B. P. Binks, P. D. I. Fletcher, and W. F. C. Sager, J. Mol. Liq. 72, 177 (1997).

    Article  CAS  Google Scholar 

  44. P. K. Sansanwal, J. Sci. Ind. Res. 65, 57 (2006).

    CAS  Google Scholar 

  45. C. Batig and H. Akbas, J. Chem. Thermodyn. 43, 1349 (2011).

    Article  Google Scholar 

  46. S.-C. Chen, S.-W. Kuo, C.-S. Liao, and F.-C. Chang, Macromolecules 41, 8865 (2008).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Surfactant Research Chair, Chemistry Department, College of Science, King Saud University, P.O. Box-2455, Riyadh, 11451, Saudi Arabia

    Ayman M. Atta, Amro K. F. Dyab, Hamad A. Al-Lohedan & Khaled A. AlJenady

  2. Petroleum Application Department, Nasr city, Egyptian Petroleum Research Institute, 11727, Cairo, Egypt

    Ayman M. Atta

  3. Chemistry Department, Faculty of Science, Minia University, 61519, Minia, Egypt

    Amro K. F. Dyab

Authors
  1. Ayman M. Atta
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Amro K. F. Dyab
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hamad A. Al-Lohedan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Khaled A. AlJenady
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ayman M. Atta.

Additional information

The article is published in the original.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Atta, A.M., Dyab, A.K.F., Al-Lohedan, H.A. et al. Novel reactive polymerizable nonyl phenol ethoxylate surfactants as emulsifier in non-aqueous emulsion polymerization. Polym. Sci. Ser. B 56, 770–787 (2014). https://doi.org/10.1134/S1560090414060025

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1560090414060025

Keywords

Search

Navigation