Thermally cleavable surfactants based on furan-maleimide diels-alder adducts

James R. McElhanon, Thomas Zifer, Steven R. Kline, David R. Wheeler, Douglas A Loy, Gregory M. Jamison, Timothy M. Long, Kamyar Rahimian, Blake A. Simmons

Research output: Contribution to journalArticle

59 Citations (Scopus)

Abstract

Two new surfactant molecules are reported that contain thermally labile Diels-Alder adducts connecting the hydrophilic and hydrophobic sections of each molecule. The two surfactants possess identical hydrophobic dodecyl tail segments but have phenol and carboxylic acid hydrophilic headgroups, respectively. Deprotonation with potassium hydroxide affords the formation of water-soluble surfactants. Room temperature aqueous solutions of both surfactants exhibit classical surface-active agent behavior similar to common analagous alkylaryl surfactant molecules. Critical micelle concentrations have been determined for each surfactant through dynamic surface tension and dye solubilization techniques. Small-angle neutron scattering measurements of the aqueous surfactant solutions indicate the presence of spherical micelles with radii of 16.5 Å for the carboxylate and 18.8 Å for the phenolate. When these surfactants are exposed to elevated temperatures (>50°C), the retro Diels-Alder reaction occurs, yielding hydrophilic and hydrophobic fragments. Aqueous solutions of each surfactant subsequently exhibit a loss of all surface-active behavior and the micellar aggregates are no longer detectable.

Original languageEnglish (US)
Pages (from-to)3259-3266
Number of pages8
JournalLangmuir
Volume21
Issue number8
DOIs
StatePublished - Apr 12 2005
Externally publishedYes

Fingerprint

furans
Surface-Active Agents
adducts
Surface active agents
surfactants
Molecules
micelles
maleimide
furan
aqueous solutions
molecules
potassium hydroxides
Potassium hydroxide
Diels-Alder reactions
Deprotonation
Critical micelle concentration
Micelles
Neutron scattering
Carboxylic Acids
Phenol

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Colloid and Surface Chemistry

Cite this

McElhanon, J. R., Zifer, T., Kline, S. R., Wheeler, D. R., Loy, D. A., Jamison, G. M., ... Simmons, B. A. (2005). Thermally cleavable surfactants based on furan-maleimide diels-alder adducts. Langmuir, 21(8), 3259-3266. https://doi.org/10.1021/la047074z

Thermally cleavable surfactants based on furan-maleimide diels-alder adducts. / McElhanon, James R.; Zifer, Thomas; Kline, Steven R.; Wheeler, David R.; Loy, Douglas A; Jamison, Gregory M.; Long, Timothy M.; Rahimian, Kamyar; Simmons, Blake A.

In: Langmuir, Vol. 21, No. 8, 12.04.2005, p. 3259-3266.

Research output: Contribution to journalArticle

McElhanon, JR, Zifer, T, Kline, SR, Wheeler, DR, Loy, DA, Jamison, GM, Long, TM, Rahimian, K & Simmons, BA 2005, 'Thermally cleavable surfactants based on furan-maleimide diels-alder adducts', Langmuir, vol. 21, no. 8, pp. 3259-3266. https://doi.org/10.1021/la047074z
McElhanon JR, Zifer T, Kline SR, Wheeler DR, Loy DA, Jamison GM et al. Thermally cleavable surfactants based on furan-maleimide diels-alder adducts. Langmuir. 2005 Apr 12;21(8):3259-3266. https://doi.org/10.1021/la047074z
McElhanon, James R. ; Zifer, Thomas ; Kline, Steven R. ; Wheeler, David R. ; Loy, Douglas A ; Jamison, Gregory M. ; Long, Timothy M. ; Rahimian, Kamyar ; Simmons, Blake A. / Thermally cleavable surfactants based on furan-maleimide diels-alder adducts. In: Langmuir. 2005 ; Vol. 21, No. 8. pp. 3259-3266.
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