Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Reexamination Certificate
2002-07-18
2004-07-27
Sanders, Kriellion A. (Department: 1714)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Processes of preparing a desired or intentional composition...
C524S354000, C524S356000, C524S546000, C524S555000, C524S588000, C524S590000
Reexamination Certificate
active
06767942
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to coatings comprising an organometallic compound, a fluorinated solvent, and co-solubilizing agent. In embodiments, the co-solubilizing agent is a fluorinated co-solubilizer. In embodiments, a fluorinated tail is added to an organometallic compound to cause the organometallic compound to become soluble in a fluorinated solvent. In embodiments, the organometallic compound, which is normally not soluble in fluorinated solvents, becomes completely miscible in fluorinated solvents. In embodiments, the co-solubilizer does not act as a catalyst, but instead, acts as a filler, and is present in the coating composition. Such coating compositions can be used in many arts such as, for example, electrical arts, electrostatographic arts, computer arts, and the like. In embodiments, the composition coating material can be useful as, for example, electrically or thermally conductive soluble fluoropolymer-ceramic hybrids or intermediates, electroluminescent fluorinated fluids or polymer coatings, photosensitive fluorinated fluids or coatings, colored fluorinated fluids or soluble polymer coatings for display devices, fluorinated carrier fluids for metal oxide film formation (where low surface tension of fluorinated fluids are desirable), thermochromic fluorescent or electrochromic fluorinated fluids or coatings, wire coatings such as electrode wire coatings, and many other applications.
Fluorinated solvents are preferred vehicles for many substances. Fluorinated solvents are preferred because they are thermally insulative, have low surface energy, can have low boiling points, and can be recyclable or recoverable,
A problem results in that many substances are not soluble in fluorinated solvents. For example, many organic molecules and many non-fluorinated or partially fluorinated compounds, are not soluble in fluorinated solvents. Specifically, most, if not all, organometallic compounds, and especially superconductors or superconductor precursors, are not soluble in fluorinated solvents.
Attempts have been made to render previously fluoro-insoluable materials soluble in fluorinated solvents. These attempts include using fluoro-ponytails (e.g., long carbon chains consisting mainly of perfluoroalkyl segments) as co-solvents. These ponytails greatly increase solubility in the fluorous phase. Many approaches are discussed below. However, in all these approaches, the co-solvent is used as a catalyst and can be separated at the end of the reaction.
A paper by the University of Leicester Department of Chemistry (http://www.le.ac.uk/chemistry/research/epsrc/egh1.html, Aug. 28, 2001) entitled, “Catalysis in the Fluorous Biphase,” discloses methods for preparation of catalysts derivatised with perfluoroalkyl substitutents to evaluate the criteria for preferential fluorous phase solubility and to investigate the influence of the perfluoroalkyl groups on the properties and activities of the metal catalyst.
A paper from
Chemtech
October 1999 (pp. 7-12) by Hans-Joachim Lehmler et al. entitled, “Liquid Ventiliation—A New Way to Deliver Drugs to Diseased Lungs?,” discloses ways of enhancing solubility in perfluorocarbon solvents of drugs.
A paper from
Science
, Vol. 275, Feb. 7, 1997 (pp. 823-826) by Armido Studer et al. entitled, “Fluorous Synthesis: A Fluorous-Phase Strategy for Improving Separation Efficiency in Organic Synthesis” teaches a “fluorous synthesis” approach in which organic molecules are rendered soluble in fluorocarbon solvents by attachment of a suitable fluorocarbon group.
A paper from
Science
, Vol. 266, Oct. 7, 1994 (pp. 72-75) by Istvan T. Horvath et al. entitled, “Facile Catalyst Separation without Water: Fluorous Biphase Hydroformulation of Olefins” discloses the application of fluorous biphase system for the extraction of rhodium from toluene and for the hydroformylation of olefins.
A paper from
Science
, Vol. 266, Oct. 7, 1994 (pp. 55-56) by J. A. Gladysz, entitled, “Are Teflon “Ponytails” the Coming Fashion for Catalysts?” discusses use of long carbon chains consisting mainly of perfluoroalkyl segments called “ponytails” appended to increase solubility in the fluorous phase and serve as de facto anchors.
A paper from
Chem. Commun
., 1998 (pp. 1531-1532) by David E. Bergbreiter et al. entitled, “A Soluble Fluorous Phase Polymer Support,” discloses preparation of a soluble fluorocarbon polymer that has reactive sites that can be used to covalently bind reagents and to render them soluble in the fluorous phase as a polymer-bound reagent.
A paper from
Journal of Pharmaceutical Sciences
, Vol. 87, No. 12, December 1998 (pp. 1585-1589) by Thomas D. Williams et al. entitled, “Solubility Enhancement of Phenol and Phenol Derivatives in Perfluorooctyl Bromide,” discusses examining the use of a hydrophobic solubilizing agent capable of interacting with model drug solutes by hydrogen bonding with the purpose of enhancing solubility in perfluorooctyl bromide.
A paper from
Journal of Fluorine Chemistry
101, 2000, (pp. 247-255) by Pravat Bhattacharyya et al., entitled “Phosphorus (III) Ligands in Fluorous Biphase Catalysis,” discloses the synthesis, coordination chemistry and catalytic applications of a series of perfluoroalkyl-substituted phosphorus (III) ligands.
A paper from
Journal of Fluorine Chemistry
99, 1999, (pp. 197-200) by Eric G. Hope et al., entitled “The Rhodium Catalyzed Hydrogenation of Styrene in the Fluorous Biphase,” discloses the use of rhodium-catalyzed hydrogenation of styrene as a system to study the influence of the perfluorocarbon and organic solvents and the perfluoroalkyl-ponytails on an application of the fluorous biphase approach to homogeneous catalysis.
A paper from
Journal of Fluorine Chemistry
100, 1999, (pp. 75-83) by Eric G. Hope et al., entitled “Fluorous Biphase Catalysis,” discusses the evolution and future prospects for the fluorous biphase approach to homogeneous catalysis.
A paper from
Journal of Fluorine Chemistry
107, 2001, (pp. 141-146) by Hans-Joachim Lehmler et al., entitled “Behaviour of Partially Fluorinated Carboxylic Acids at the Air-Water Interface,” discloses langmuir isotherms for several acids.
A paper from
Chemtracts-Inorganic Chemistry
Vol. 7 1995 (pp. 14-18) by I. T. Horvath et al., entitled, “Facile Catalyst Separation Without Water: Fluorous Biphase Hydroformylation of Olefins,” discloses the utility of a new simple scheme to effect catalyst/product separation in homogeneous catalysis.
However, it is sometimes desired that a fluoro-solubilizing co-solvent not be used as a catalyst as it is used in the above listed experiments. This is necessary when it is not suitable to include the step of separating the catalyst from the fluorinated solution. Such a situation may include creating a coating by mixing several compounds together.
SUMMARY OF THE INVENTION
Embodiments of the present invention include: an organometallic coating composition comprising an organometallic compound, a fluorinated solvent, and a co-solubilizer comprising a fully fluorinated polymer, wherein said organometallic compound is miscible in said organometallic coating composition.
Embodiments further include: an organometallic coating composition comprising an organometallic compound selected from the group consisting of a superconductor and superconductor precursor, a fluorinated solvent, and a co-solubilizer comprising a fully fluorinated polymer, wherein said organometallic compound is miscible in said organometallic coating composition.
In addition, embodiments include: an organometallic coating composition comprising an organometallic compound, a fluorinated solvent, and a copolymer of tetrafluoroethylene and an oxy-halo perfluoropolymer, wherein said organometallic compound is miscible in said organometallic coating composition.
DETAILED DESCRIPTION
The present invention relates to organometallic coating compositions for many applications. The coating composition comprises an organometallic compound, a co-solubilizer, and a fluorinated solvent. In embodiments, the co-solubilizin
Badesha Santokh S.
Bingham George J.
Gervasi David J.
Bade Annette L.
Sanders Kriellion A.
Xerox Corporation
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