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Title: Thermally cleavable surfactants

Abstract

Two new surfactant molecules are reported which contain thermally labile Diels-Alder adducts connecting the polar and non-polar sections of each molecule. The two surfactants possess identical non-polar dodecyl tail segments but exhibit different polar headgroups. The surfactants become soluble in water when anionic salts are formed through the deprotonation of the surfactant headgroups by the addition of potassium hydroxide. When either surfactant is exposed to temperature above about 60.degree. C., the retro Diels-Alder reaction occurs, yielding hydrophilic and hydrophobic fragments and the aqueous solutions of the surfactants subsequently exhibit loss of all surface-active behavior.

Inventors:
 [1];  [2];  [1];  [3];  [3];  [3];  [4];  [3];  [3]
  1. Manteca, CA
  2. San Francisco, CA
  3. Albuquerque, NM
  4. Urbana, IL
Issue Date:
Research Org.:
Sandia National Lab. (SNL-CA), Livermore, CA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
908535
Patent Number(s):
7022861
Assignee:
Sandia National Laboratories (Livermore, CA)
Patent Classifications (CPCs):
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
DOE Contract Number:  
AC04-94AL85000
Resource Type:
Patent
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

McElhanon, James R, Simmons, Blake A, Zifer, Thomas, Jamison, Gregory M, Loy, Douglas A, Rahimian, Kamyar, Long, Timothy M, Wheeler, David R, and Staiger, Chad L. Thermally cleavable surfactants. United States: N. p., 2006. Web.
McElhanon, James R, Simmons, Blake A, Zifer, Thomas, Jamison, Gregory M, Loy, Douglas A, Rahimian, Kamyar, Long, Timothy M, Wheeler, David R, & Staiger, Chad L. Thermally cleavable surfactants. United States.
McElhanon, James R, Simmons, Blake A, Zifer, Thomas, Jamison, Gregory M, Loy, Douglas A, Rahimian, Kamyar, Long, Timothy M, Wheeler, David R, and Staiger, Chad L. Tue . "Thermally cleavable surfactants". United States. https://www.osti.gov/servlets/purl/908535.
@article{osti_908535,
title = {Thermally cleavable surfactants},
author = {McElhanon, James R and Simmons, Blake A and Zifer, Thomas and Jamison, Gregory M and Loy, Douglas A and Rahimian, Kamyar and Long, Timothy M and Wheeler, David R and Staiger, Chad L},
abstractNote = {Two new surfactant molecules are reported which contain thermally labile Diels-Alder adducts connecting the polar and non-polar sections of each molecule. The two surfactants possess identical non-polar dodecyl tail segments but exhibit different polar headgroups. The surfactants become soluble in water when anionic salts are formed through the deprotonation of the surfactant headgroups by the addition of potassium hydroxide. When either surfactant is exposed to temperature above about 60.degree. C., the retro Diels-Alder reaction occurs, yielding hydrophilic and hydrophobic fragments and the aqueous solutions of the surfactants subsequently exhibit loss of all surface-active behavior.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2006},
month = {4}
}

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Works referenced in this record:

Synthesis and properties of 2-alkoxy-N, N-Dimethylethylamine N-oxides
journal, March 1985


Diels-Alder Reactions with Some N-Substituted Maleimides
journal, January 1977


Ozone-cleavable gemini surfactants, a new candidate for an environmentally friendly surfactant
journal, January 1998


New Thermally Remendable Highly Cross-Linked Polymeric Materials
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Thermally Responsive Dendrons and Dendrimers Based on Reversible Furan-Maleimide Diels−Alder Adducts
journal, August 2001


A Thermally Re-mendable Cross-Linked Polymeric Material
journal, March 2002


Removable foams based on an epoxy resin incorporating reversible Diels-Alder adducts
journal, June 2002


Synthesis and characterization of bismaleimides from epoxy resins
journal, April 1992