Advertisement

Surfactants Containing Hydrolyzable Bonds

  • Dan Lundberg
  • Maria Stjerndahl
  • Krister Holmberg
Chapter
Part of the Advances in Polymer Science book series (POLYMER, volume 218)

Abstract

There is a growing demand for hydrolyzable surfactants, i.e., surfactants that break down ina controlled way by changing the pH. Environmental concern is the main driving force behind currentinterest in these surfactants, but they are also of interest in applications where surfactants are neededin one stage but later undesirable at another stage of a process. This chapter summarizes the fieldof hydrolyzable surfactants with an emphasis on their more recent development. Surfactants that break downeither on the acid or on the alkaline side are described. It is shown that the susceptibility to hydrolysisfor many surfactants depends on whether or not the surfactant is in the form of micelles or as free unimersin solution. It is shown that whereas nonionic ester surfactants are more stable above the CMC (micellarretardation), cationic ester surfactants break down more readily when aggregated than when present as unimers(micellar catalysis).

Keywords

Linear Alkylbenzene Sulfonate Polar Head Group Alcohol Ethoxylates Hydrolyzable Bond Micellar Catalysis 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Jaeger DA (1995) Supramol Chem 5:27–30 CrossRefGoogle Scholar
  2. 2.
    Tehrani-Bagha AR, Holmberg K (2007) Curr Opin Colloid Interface Sci 12:81–91 CrossRefGoogle Scholar
  3. 3.
    Holmberg K (2001) Cleavable Surfactants. In: Texter J (ed) Reactions and Synthesis in Surfactant Systems. Marcel Dekker, New York Google Scholar
  4. 4.
    Stjerndahl M, Lundberg D, Holmberg K (2003) Cleavable surfactants. In: Holmberg K (ed) Novel Surfactants, 2nd ed. Marcel Dekker, New York Google Scholar
  5. 5.
    Holmberg K, Jönsson B, Kronberg B, Lindman B (2002) Surfactants and Polymers in Aqueous Solution, 2nd ed. Marcel Dekker, New York CrossRefGoogle Scholar
  6. 6.
    Holmberg K (1993) Surf Coatings Int 76:481–448 Google Scholar
  7. 7.
    Swisher RD (1987) Surfactant Biodegradation. Marcel Dekker, New York Google Scholar
  8. 8.
    White GF, Russel NJ (1995) What is biodegradation? In: Karsa DR (ed) Biodegradability of Surfactants. Blackie, Glascow Google Scholar
  9. 9.
    Brown D (1995) Introduction to surfactant biodegradation. In: Karsa DR (ed) Biodegradability of Surfactants. Blackie, Glascow Google Scholar
  10. 10.
    Painter HA (1995) Biodegradability testing. In: Karsa DR (ed) Biodegradability of Surfactants. Blackie, Glascow Google Scholar
  11. 11.
    Painter HA (1995) Testing strategy and legal requirements. In: Karsa DR (ed) Biodegradability of Surfactants. Blackie, Glascow Google Scholar
  12. 12.
    van Ginkel CG (1996) Biodegradation 7:151–164 CrossRefGoogle Scholar
  13. 13.
    van Ginkel CG, Stroo CA, Kroon AGM (1993) Tenside Surfact Deterg 30:213–216 Google Scholar
  14. 14.
    Balson T, Felix MSB (1995) Biodegradability of non-ionic surfactants. In: Karsa DR (ed) Biodegradability of Surfactants. Blackie, Glascow Google Scholar
  15. 15.
    Huber M, Meyer U, Rys P (2000) Environ Sci Technol 34:1737–1741 CrossRefGoogle Scholar
  16. 16.
    Marcomini A, Zanette M, Pojana G, Suter MJF (2000) Chem 19:549–554 Google Scholar
  17. 17.
    Carvalho G, Novais JM, Pinheiro HM (2003) Environ Technol 24:109–114 CrossRefGoogle Scholar
  18. 18.
    Stjerndahl M, Holmberg K (2003) J Surfact Deterg 6:311–318 CrossRefGoogle Scholar
  19. 19.
    Stjerndahl M, van Ginkel CG, Holmberg K (2003) J Surfact Deterg 6:319–324 CrossRefGoogle Scholar
  20. 20.
    Lundberg D, Stjerndahl M, Holmberg K (2005) Langmuir 21:8658–8663 CrossRefGoogle Scholar
  21. 21.
    Overkempe C, Annerling A, van Ginkel CG, Thomas PC, Boltersdorf D, Speelman J (2003) Esterquats. In: Holmberg K (ed) Novel Surfactants. Marcel Dekker, New York Google Scholar
  22. 22.
    Garcia MT, Campos E, Sanchez-Leal J, Ribosa I (2000) Chemosphere 41:705–710 CrossRefGoogle Scholar
  23. 23.
    Steichen DS (2002) Cationic Surfactants. In: Holmberg K (ed) Handbook of Applied Surface and Colloid Chemistry, Vol. 1. Wiley, New York Google Scholar
  24. 24.
    Jacques A, Schramm CJ (1997) Fabric softeners. In: Lai K-Y (ed) Liquid Detergents. Marcel Dekker, New York Google Scholar
  25. 25.
    Wright MR (1968) J Chem Soc B 5:548–550 CrossRefGoogle Scholar
  26. 26.
    Wright MR (1969) J Chem Soc B 6:707–710 CrossRefGoogle Scholar
  27. 27.
    Thompson RA, Allenmark S (1989) Acta Chem Scand 43:690–693 CrossRefGoogle Scholar
  28. 28.
    Thompson RA, Allenmark S (1992) J Colloid Interface Sci 148:241–246 CrossRefGoogle Scholar
  29. 29.
    Lundberg D, Holmberg K (2004) J Surfact Deterg 7:239–246 CrossRefGoogle Scholar
  30. 30.
    Lundberg D, Ljusberg-Wahren H, Norlin A, Holmberg K (2004) J Colloid Interface Sci 278:478–487 CrossRefGoogle Scholar
  31. 31.
    Romsted LS (1977) A general kinetic theory of rate enhancements for reactions between organic substrates and hydrophilic ions in micellar systems. In: Mittal KL (ed) Micellization, Solubilization, Microemulsions. Plenum Press, New York Google Scholar
  32. 32.
    Rozycka-Roszak B, Przestalski S, Witek S (1988) J Colloid Interface Sci 125:80–85 CrossRefGoogle Scholar
  33. 33.
    Karlberg M, Stjerndahl M, Lundberg D, Piculell L (2005) Langmuir 21:9756–9763 CrossRefGoogle Scholar
  34. 34.
    Lindstedt M, Allenmark S, Thompson RA, Edebo L (1990) Agents Chemother 34:1949–1954 CrossRefGoogle Scholar
  35. 35.
    Stjerndahl M, Holmberg K (2005) J Colloid Interface Sci 291:570–576 CrossRefGoogle Scholar
  36. 36.
    Rosen M (1989) Surfactants and Interfacial Phenomena, 2nd ed. Wiley, New York Google Scholar
  37. 37.
    Corti M, Degiorgio V, Zulauf M (1982) Phys Rev Lett 48:1617–1620 CrossRefGoogle Scholar
  38. 38.
    Ohta A, Takiue T, Ikeda N, Aratono M (2001) J Solution Chem 30:335–350 CrossRefGoogle Scholar
  39. 39.
    Stjerndahl M, Holmberg K (2005) Surfact Deterg 8:1–6 Google Scholar
  40. 40.
    Jaeger DA (1995) Supramol Chem 5:27–30 CrossRefGoogle Scholar
  41. 41.
    Bieniecki A, Wilk KA, Gapinski J (1997) J Phys Chem B 101:871–875 CrossRefGoogle Scholar
  42. 42.
    Sokolowski A, Bieniecki A, Wilk KA, Burczyk B (1995) Colloids Surfaces A 98:73–82 CrossRefGoogle Scholar
  43. 43.
    Wang G-W, Yuan X-Y, Liu Y-C, Lei X-G, Guo Q-X (1995) J Am Oil Chem Soc 72:83–87 CrossRefGoogle Scholar
  44. 44.
    Wang G-W, Liu Y-C, Yuan X-Y, Lei X-G, Guo Q-X (1995) J Colloid Interface Sci 173:49–54 CrossRefGoogle Scholar
  45. 45.
    Sokolowski A, Piasecki A, Burczyk B (1992) J Am Oil Chem Soc 69:633–638 CrossRefGoogle Scholar
  46. 46.
    Wang G-W, Yuan X-Y, Liu Y-C, Lei X-G (1994) J Am Oil Chem Soc 71:727–730 CrossRefGoogle Scholar
  47. 47.
    Wilk KA, Bieniecki A, Burczyk B, Sokolowski A (1994) J Am Oil Chem Soc 71:81–85 CrossRefGoogle Scholar
  48. 48.
    Galante DC, Hoy RC (1996) Eur Patent Appl EP 0742177 A1 Google Scholar
  49. 49.
    Hoy RC, Joseph AF (1996) INFORM 7:428–429 Google Scholar
  50. 50.
    Piasecki A (1985) J Prakt Chem 327:731–738 CrossRefGoogle Scholar
  51. 51.
    Bieniecki A, Wilk KA (1995) J Phys Org Chem 8:71–76 CrossRefGoogle Scholar
  52. 52.
    Yamamura S, Nakamura M, Kasai K, Sato H, Takeda T (1991) J Jpn Oil Chem Soc 40:1002–1006 CrossRefGoogle Scholar
  53. 53.
    Masuyama A, Ono D, Yamamoto A, Kida T, Nakatsuji Y, Takeda T (1995) J Jpn Oil Chem Soc 44:446–450 CrossRefGoogle Scholar
  54. 54.
    Ono D, Yamamura S, Nakamura M, Takeda T, Masuyama A, Nakatsuji Y (1995) J Am Oil Chem Soc 72:853–856 CrossRefGoogle Scholar
  55. 55.
    Ono D, Masuyama A, Nakatsuji Y, Okahara M, Yamamura S, Takeda T (1993) J Am Oil Chem Soc 70:29–36 CrossRefGoogle Scholar
  56. 56.
    Kida T, Morishima N, Masuyama A, Nakatsuji Y (1994) J Am Oil Chem Soc 71:705–710 CrossRefGoogle Scholar
  57. 57.
    Song B-K, Wolf K (1995) DWI Rep 114:549–554 Google Scholar
  58. 58.
    Hellberg P-E, Bergström K (2002) An ortho ester based surfactant, its preparation and use. Eur Patent 1042266 Google Scholar
  59. 59.
    Hellberg P-E, Bergström K, Juberg M (2000) J Surfact Deterg 3:369–379 CrossRefGoogle Scholar
  60. 60.
    Cordes EH, Bull HG (1974) Chem Rev 74:581–603 CrossRefGoogle Scholar
  61. 61.
    Potts RA, Schaller RA (1993) J Chem Ed 70:421–424 CrossRefGoogle Scholar
  62. 62.
    Bergh M, Shao LP, Magnusson K, Gäfvert E, Nilsson JLG, Karlberg A (1999) J Pharm Sci 88:483–488 CrossRefGoogle Scholar
  63. 63.
    Hellberg P-E (2002) Licentiate thesis. Chalmers University of Technology, Göteborg, Sweden Google Scholar
  64. 64.
    Bergström K, Hellberg P-E (1998) PCT Int Patent WO 98/00452 Google Scholar
  65. 65.
    Mohlin K, Holmberg K (2006) Nonionic ortho esters used as emulsifiers. J Colloid Interface Sci 299:435–442 CrossRefGoogle Scholar
  66. 66.
    Hellberg P-E (2002) J Surfactants Deterg 5:217–227 CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2008

Authors and Affiliations

  • Dan Lundberg
    • 1
  • Maria Stjerndahl
    • 1
  • Krister Holmberg
    • 1
  1. 1.Applied Surface ChemistryChalmers University of TechnologyGöteborgSweden

Personalised recommendations