Phosphate fluorosurfactants for use in carbon dioxide

Drying and gas or vapor contact with solids – Process – With contacting of material treated with solid or liquid agent

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C510S175000, C134S003000, C438S906000

Reexamination Certificate

active

06684525

ABSTRACT:

FIELD OF THE INVENTION
The present invention generally relates to surfactants that exhibit solubility in carbon dioxide, and systems utilizing the same.
BACKGROUND OF THE INVENTION
The use of carbon dioxide as a clean, abundant, and tunable solvent is potentially environmentally beneficial, and accordingly it is being investigated in a number of applications including, for example, cleaning protocols, coatings, and polymer production and processing. See e.g., Wells, S. L.; DeSimone, J.
Angew. Chem. Int. Ed.
2001, 40, 518. Notwithstanding the above potential benefits, carbon dioxide is often limited in that many materials such as water exhibit limited solubility therein.
In response to these possible solubility limitations, fluorosurfactants have been developed to potentially assist in the dispersion of water in carbon dioxide. See e.g., Harrison, K.; Goveas, J.; Johnston, K. P.; O'Rear, E. A.
Langmuir
1994, 10, 3536, Johnston, K. P.; Harrison, K. L.; Clarke, M. J.; Howdle, S. M.; Heitz, M. P.; Bright, F. V.; Carlier, C.; Randolph, T. W.
Science
1996, 271, 624, Eastoe, J.; Bayazit, Z.; Martel, S.; Steytler, D. C.; Hennan, R. K.
Langmuir
1996, 12, 1423, Eastoe, J.; Cazelles, B. M. H.; Steytler, D. C.; Holmes, J. H.; Pitt, A. R.; Wear, T. J.; Heenan, R. K.
Langmuir
1997, 13, 6980, Zielinski, R. G.; Kline, S. R.; Kaler, E. W.; Rosov, N.
Langmuir
1997, 13, 3934, Eastoe, J.; Downer, A.; Paul, A.; Steytler, D. C.; Rumsey, E.; Penfold, J.; Heenan, R. K.
Phys. Chem. Chem. Phys.
2000, 2, 5235, Lee Jr., C. T.; Bhargava, P.; Johnston, K. P.
J. Phys. Chem. B
2000, 104, 4448, Lee Jr., C. T.; Johnston, K. P.; Dai, H. J.; Cochran, H. D.; Melnichenko, Y. B.; Wignall, G. D.
J. Phys. Chem. B
2001, 105, 3540, and Liu, Z. -T.; Erkey, C.
Langmuir
2001, 17, 274. Accordingly, water-in-carbon dioxide (W/C) microemulsions containing appreciable water quantities have been achieved, allowing for their use in a number of applications such as nanoparticle synthesis, organic reactions, voltammetric measurements, and enzymatic conversions. See e.g., Holmes, J. D.; Bhargava, P. A.; Korgel, B. A.; Johnston, K. P.
Langmuir
1999, 15, 6613, Ji, M.; Chen, X.; Wai, C. M.; Fulton, J. L.
J. Am. Chem. Soc.
1999, 121, 2631, Jacobson, G. B.; Lee Jr., C. T.; Johnston, K. P.
J. Org. Chem.
1999, 64, 1201, Ode, H.; Hunt, F.; Kithara, S.; Way, C. M.
Anal. Chem.
2000, 72, 4738, Lee, D.; Hutchison, J. C.; Demimonde, J. M.; Murray, R. M.
J. Am. Chem. Soc.
2001, 123, 8406, Holmes, J. D.; Settler, D. C.; Rees, G. D.; Robinson, B. H.
Languor
1998, 14, 6371, and Kane, M. A.; Baker, G. A.; Pander, S.; Bright, F. V.
Languor
2000, 16, 4901. W/C systems have also been the subject of computational treatments. See e.g., Satanically, S.; Cui, S. T.; Cummings, P. T.; Cochran, H. D.
Languor
1999, 15, 5188.
Nonetheless, inspite of any advantages of these systems, there remains a need in the art for surfactants and systems employing the same that allow for improved volatilization of various materials in carbon dioxide, such as, for example, water.
SUMMARY OF THE INVENTION
In one aspect, the invention provides a method of removing water from a first composition of matter. The method comprises contacting a first composition of matter comprising water with a second composition of matter comprising: (1) at least one surfactant comprising at least one phosphate group and (2) a solvent comprising carbon dioxide, wherein at least a portion of the surfactant is soluble in the solvent, such that the at least one surfactant removes at least a portion of the water from the first composition.
In another aspect, the invention provides a method of applying a surfactant to a substrate. The method comprises providing a composition of matter comprising at least one surfactant comprising (1) at least one phosphate group and (2) a solvent comprising carbon dioxide, wherein at least a portion of the surfactant is soluble in the solvent; and applying the composition of matter onto a substrate such that the carbon dioxide separates from the surfactant and wherein the surfactant coats the substrate.
In another aspect, the invention provides compositions of matter comprising (1) at least one surfactant comprising at least one phosphate group and (2) a solvent comprising carbon dioxide.
These and other aspects of the invention are described in greater detail herein.


REFERENCES:
patent: 5344930 (1994-09-01), Riess et al.
patent: 5573757 (1996-11-01), Riess et al.
patent: 5648362 (1997-07-01), Riess et al.
patent: 5650393 (1997-07-01), Pavia et al.
patent: 5676705 (1997-10-01), Jureller et al.
patent: 5679459 (1997-10-01), Riess et al.
patent: 5683473 (1997-11-01), Jureller et al.
patent: 5733526 (1998-03-01), Trevino et al.
patent: 5846516 (1998-12-01), Riess et al.
patent: 5858022 (1999-01-01), Romack et al.
patent: 5904933 (1999-05-01), Riess et al.
patent: 5965258 (1999-10-01), Riess et al.
patent: 5980936 (1999-11-01), Krafft et al.
patent: 6114295 (2000-09-01), Murphy
patent: 6398875 (2002-06-01), Cotte et al.
patent: 6562146 (2003-05-01), DeYoung et al.
patent: 90/15807 (1990-12-01), None
patent: 95/09606 (1995-04-01), None
patent: 97/03644 (1997-02-01), None
International Search Report for PCT/US01/29812, Date of mailing Jan. 3, 2002.
Consani et al.; “Observations on the Solubility of Surfactants and Related Molecules in Carbon Dioxide at 50 °C”,The Journal of Supercritical Fluids, 3 (2): 51-65 (1990).
DuPont, “DuPont™ Zonyl® Flurosurfactants,” DuPont, 1-12 (2001).
DuPont, “DuPont™ Zonyl® FSP Flurosurfactant, ” DuPont, 1-6 (2001).
Eastoe et al.; “Droplet Structure in a Water-in-C02Microemulsion,”Langmuir, 12 (6): 1423-1424 (1996).
Eastoe et al.; “Fluoro-surfactants at air/water and water/CO2interfaces,”Physical Chemistry Chemical Physics., 2 (22): 5235-5242 (2000).
Eastoe et al.; “Water-in- C02Microemulsions Studied by Small-Angle Neutron Scattering,”Langmuir, 13 (26): 6980-6984 (1997).
Giulieri et al.; “Can the formation of vesicles from single-chain perfluoroalkylated amphiphiles be predicted?”Colloids and Surfaces A: Physicochemical and Engineering Aspects, 84: 121-127 (1994).
Harrison et al.; “Water-in-Carbon Dioxide Microemulsions with a Fluorocarbon-Hydrocarbon Hybrid Surfactant,”Langmuir, 10 (10): 3536-3641 (1994).
Holmes et al.; “Bioconversions in a Water-in-C02Microemulsion,”Langmuir, 14 (22): 6371-6376 (1998).
Holmes et al.; “Synthesis of Cadmium Sulfide Q Particles in Water-in-C02Microemulsions,”Langmuir, 15 (20): 6613-6615 (1999).
Imae et al.; “Phase Separation in Hybrid Langmuir-Blodgett Films of Perfluorinated and Hydrogenated Amphiphiles. Examination by Atomic Force Microscopy,”Langmuir, 16 (2): 612-621 (2000).
Imae et al.; “Fibril-vesicle transition and their structures-investigation by microscopy and small-angle scattering,”Progr Colloid Polym Sci, 106: 52-56 (1997).
Jacobson et al.; “Organic Synthesis in Water/Carbon Dioxide Microemulsions,”J. Org. Chem., 64 (4): 1201-1206 (1999).
Ji et al.; “Synthesizing and Dispersing Silver Nanoparticles in a Water-in-Supercritical Carbon Dioxide Microemulsion,”J. Am. Chem. Soc., 121 (11): 2631-2632 (1999).
Johnston et al.; “Water-in-Carbon Dioxide Microemulsions: An Environment for Hydrophiles Including Proteins,”Science, 271: 624-626 (1996).
Kane et al.; “Performance of Cholesterol Oxidase Sequestered within Reverse Micelles Formed in Supercritical Carbon Dioxide,”Langmuir, 16 (11): 4901-4905 (2000).
Krafft et al.; “Highly fluorinated amphiphiles and colloidal systems, and their applications in the biomedical field. A contribution”Biochimie, 80 (5-6): 489-514 (1998).
Krafft et al.; “Enhanced Proclivity to self-aggregation of phosphorus-based amphiphiles when perfluoroalkylated: the (perfluoroalkyl)alkyldimorpholinophosphates,”Phosphorus, Sulfur and Silicon, 109-110: 281-284 (1996).
Krafft et al.; “Supramolecular assemblies from single-chain perfluoroalkylated phosphorylated amphiphiles,”Colloids and Surfaces A: Physicochemical and Engineering Aspects, 84: 113-119 (1994).
Lee D. et al.; “Diffusive Transport of Micelles and Monomeric Solutes in Supercritical

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Phosphate fluorosurfactants for use in carbon dioxide does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Phosphate fluorosurfactants for use in carbon dioxide, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Phosphate fluorosurfactants for use in carbon dioxide will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3301609

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.