Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2006-04-04
2006-04-04
Dentz, Bernard (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C252S183110
Reexamination Certificate
active
07022861
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° 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.
REFERENCES:
patent: 6271335 (2001-08-01), Small et al.
patent: 6337384 (2002-01-01), Loy et al.
patent: 6403753 (2002-06-01), Loy et al.
patent: 6600076 (2003-07-01), Abbott et al.
patent: 2003/0116272 (2003-06-01), Aubert
patent: 0 758314 (1999-09-01), None
patent: WO 97/14402 (1997-04-01), None
patent: WO 99/05241 (1999-02-01), None
patent: WO 02/064945 (2002-08-01), None
patent: WO 02/097393 (2002-12-01), None
Khattab et al, Journal fuer Praktische Chemie (Liepzig), vol. 319 (3), p. 432-438 (1977).
Aubert J.; “Thermally Removable Epoxy Adhesives Incorporating Thermally Reversible Diels-Alder Adducts”Journal of Adhesion, 2003, vol. 79, pp. 609-616.
Chen, X.; Wudl, F.; Mal, A.; Shen, H. Nutt, S.; “New Thermally Remendable Highly Cross-Linked Polymeric Materials”Macromolecules, 2003, vol. 36, pp. 1802-1807.
Chen, X.; Wudl, F.; Mal, A.; Shen, H. Nutt, S.; “A Thermally Re-mendable Cross-Linked Polymeric Material”Science, 2002, vol. 295, pp. 1698-1702.
McElhanon, J.; Russick, E.; Wheeler, D.; Loy, D.; Aubert, J.; “Removable Foams Based on an Epoxy Resin Incorporating Reversible Diels-Alder Adducts”Journal of Applied Polymer Science, 2002, vol. 85, pp. 1496-1502.
McElhanon, J.; Wheeler,; “Thermally Responsive Dendrons and Dendrimers Based on Reversible Furan-Maleimide Diels-Alder Adducts”Organic Letters, 2001, vol. 3(17), pp. 2681-2683.
Su, D.; Jeager, D.; “High regioselectivity in the Diels-Alder reaction of a surfactant dienophile resulting from a short tether between their functional groups and head groups”Tetrahedron Letters, 1999, vol. 40(45); pp. 7871-7874.
Masuyama, A.; Endo, C.; Takeda, S-Y.; Nojima, M; “Ozone-cleavable Gemini surfactants, a new candidate for an environmentally friendly surfactant”Chemical Communications, 1998, Issue 18, pp. 2023-2024.
Goussé, C.; Gandini, A.; Hodge P.; “Application of the Diels-Alder Reaction to Polymers Bearing Furan Moieties. 2. Diels-Alder and Retro-Diels-Alder Reactions Involving Furan Rings In Some Styrene Copolymers”;Macromolecules, 1998, vol. 31 pp. 314-321.
Park, J. O.; Jang, S. H.; “Synthesis and Characterization of Bismaleimides from Epoxy Resins”Journal of Polymer Science: Part A: Polymer Chemistry, 1992, vol. 30, pp. 723-729.
Hayashi, Y.; Shirai, F.; Shimizu, T.; Nagano, Y.; Teramura, K.; “Synthesis and Properties of 2-Alkoxy-N, N-Dimethylethylamine N-Oxides”Journal of American Oil Chemists' Society; 1985, vol. 62 (3) pp. 555-557.
Keana, J.; Guzikowski, A.; Morat, C.; Volwerk, J.; “Detergents Containing a 1,3-Diene Group in the Hydrophobic Segment. Facile Chemical Modification by a Diels-Alder Reaction Hydrophilic Dienophiles in Aqueous Solution”;The Journal of Organic Chemistry, 1983, vol. 48(16), pp. 2661-2666.
Piancatelli, G.; Scetrri, A.; D'Auria, M.; “Oxidative ring opening of furan derivatives to α,β-unsaturated γ-dicarbonyl compounds, useful intermediates for 3-oxocyclopentanes synthesis”Tetrahedron, 1980, vol. 36(5); pp. 661-663.
Jamison Gregory M.
Long Timothy M.
Loy Douglas A.
McElhanon James R.
Rahimian Kamyar
Dentz Bernard
Evans Timothy P.
Sandia National Laboratories
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