Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Nitrogen-containing reactant
Reexamination Certificate
2007-12-18
2007-12-18
Truong, Duc (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Nitrogen-containing reactant
C528S220000, C528S228000, C528S398000, C528S482000, C528S485000, C528S487000, C528S488000, C528S503000, C525S540000
Reexamination Certificate
active
10969456
ABSTRACT:
A PBI compound includes imidazole nitrogens at least a portion of which are substituted with a moiety containing a carbonyl group, the substituted imidazole nitrogens being bonded to carbon of the carbonyl group. At least 85% of the nitrogens may be substituted. The carbonyl-containing moiety may include RCO—, where R is alkoxy or haloalkyl. The PBI compound may exhibit a first temperature marking an onset of weight loss corresponding to reversion of the substituted PBI that is less than a second temperature marking an onset of decomposition of an otherwise identical PBI compound without the substituted moiety. The PBI compound may be included in separatory media. A substituted PBI synthesis method may include providing a parent PBI in a less than 5 wt % solvent solution. Substituting may use more than 5 equivalents in relation to the imidazole nitrogens to be substituted.
REFERENCES:
patent: RE26065 (1966-07-01), Marvel et al.
patent: 3408366 (1968-10-01), White
patent: 3518234 (1970-06-01), Hara et al.
patent: 3549603 (1970-12-01), Chenevey et al.
patent: 3578644 (1971-05-01), Trischler
patent: 3708439 (1973-01-01), Sayigh et al.
patent: 3943125 (1976-03-01), Gerber
patent: 4020142 (1977-04-01), Davis et al.
patent: 4154919 (1979-05-01), Sheratte
patent: 4312976 (1982-01-01), Choe
patent: 4483977 (1984-11-01), Conciatori et al.
patent: 4530922 (1985-07-01), Mogerg
patent: 4599388 (1986-07-01), Bower et al.
patent: 4693824 (1987-09-01), Sansone
patent: 4693825 (1987-09-01), Trouw
patent: 4759986 (1988-07-01), Marikar et al.
patent: 4771117 (1988-09-01), Citron et al.
patent: 4814399 (1989-03-01), Sansone et al.
patent: 4814400 (1989-03-01), Sansone
patent: 4868249 (1989-09-01), Sansone
patent: 4898917 (1990-02-01), Sansone
patent: 4933397 (1990-06-01), Sansone et al.
patent: 4997892 (1991-03-01), Sansone et al.
patent: 5017420 (1991-05-01), Marikar et al.
patent: 5290884 (1994-03-01), Calundann et al.
patent: 5389326 (1995-02-01), Kasowski et al.
patent: 5599639 (1997-02-01), Sansone et al.
patent: 5945233 (1999-08-01), Onorato et al.
patent: 6124060 (2000-09-01), Akita et al.
patent: 6323301 (2001-11-01), Smith et al.
Roziere, Jacques and Jones, Deborah,Non-Fluorinated Polymer Materials for Proton Exchange Membrane Fuel Cells, Annu. Rev. Mater. Res. 2003, vol. 33, pp. 503-555.
Burns, Ryan and Koros, William,Structure—Property Relationships for Poly(pyrrolone-imide)Gas Separation Membranes, Macromolecules 2003, 36, pp. 2374-2381.
Schuster, Martin F.H. and Meyer, Wolfgang,Anhydrous Proton-Conducting Polymers, Annu. Rev. Mater. Res, 2003, vol. 33, pp. 233-261.
Haile, Sossina M.,Fuel Cell Materials and Components, Science Direct, Acta Materialia 51, 2003, pp. 5981-6000.
Wijmans, J.G. and Baker R.W.,The Solution-Diffusion Model: A Review, Journal of Membrane Science 107, 1995, pp. 1-21.
Jones, Deborah and Roziere, Jacques,Recent Advances in the Functionalisation of Polybenzimidazole and Polyetherketone for Fuel Cell Applications, Journal of Membrane Science 185, 2001, pp. 41-58.
Barrer, R.M., Tras. Faraday Soc. 1939, vol. 35, p. 628.
Rogers, C., et al,Studies in the Gas and Vapor Permeability of Plastic Films and Coated Papers, Parts I and II, TAPPI 1956, vol. 39, p. 737.
Vogel, Herward and Marvel, C.S.,Polybenzimidazoles, New Thermally Stable Polymers, Journal of Polymer Science, vol. 1, 1961, pp. 511-539.
Gieselman, Melinda and Reynolds, John,Aramid and Imidazole Based Polyelectrolytes: Physical Properties and Ternary Phase Behavior with Poly(Benzobisthiazole)in Methanesulfonic Acid, Macromolecules, 1993, vol. 26, pp. 5633-5642.
Gieselman, Melinda and Reynolds, John,Water-Soluable Polybenzimidazole-Based Polyelectrolytes, Macromolecules, 1992, vol. 25, pp. 4832-4834.
Van Amerongen, G.J.,Permeation, Diffusion and Solution of Gases in Organic-inorganic hybrid moiety Polymers, J. App. Physics, 1946, vol. 17, p. 972.
M. Chanda and G. L. Rempel,Polybenzimidazole resin-based new chelating agents. Uranyl and ferric ion selectivity of resins with anchored dimethylglyoxime, Reactive Polymers, vol. 11, 1989, pp. 165-176.
M. Chanda and G. L. Rempel,Polybenzimidazole resin based new chelating agents. Palladium(II)and platinum(IV)sorption on resin with immobilized dithiooxamide, Reactive Polymers, vol. 12, Issue 1, Feb. 1990, pp. 83-94.
M. Chanda and G. L. Rempel,Polybenzimidazole resin based new chelating agents uranyl ion selectivity of resins with immobilized glyoxal-bis-2-hydroxyanil and salicylaldehyde-ethylenediimine, Reactive Polymers, vol. 13, Issues 1-2, Sep. 1990, pp. 103-119.
M. H. Kotze, B. R. Green and P. Ellis,Fibrous weak-base anion exchangers from a polybenzimidazole staple for the extraction of gold cyanide, Reactive Polymers, vol. 14, Issue 2, Mar. 1991, pp. 129-141.
M. Chanda and G. L. Rempel,New chelating resins based on polybenzimidazole. Selective sorption of copper(II)from ammoniacal media on resin with anchored cysteine, Reactive Polymers, vol. 16, Issue 1, Dec. 1991, pp. 29-39.
M. Chanda and G. L. Rempel,Removal of uranium from acidic sulfate solution by ion exchange on poly(4-vinylpyridine)and polybenzimidazole in protonated sulfate form, Reactive Polymers, vol. 17, Issue 2, May 1992, pp. 159-174.
James D. White, Paul R. Blakemore, Selena Milicevic, Satish C. Choudhry, Joseph Cupano, and Lucia Serico,Conversion of Carbamates to Amidosulfones and Amides. Synthesis of the [14C]-Labeled Antiobesity Agent Ro23-7637. Org. Lett., 2002, 4(10) pp. 1803-1806.
Hirokazu Sumiyoshi, Takafumi Shimizu, Miho Katoh, Yoshiyasu Baba, and Mikiko Sodeoka,Solution-Phase Parallel Synthesis of Carbamates Using Polymer-Bound N-Hydroxysuccinimide, Org. Lett.; 2002; 4(22) pp. 3923-3926.
Amanda R. Murphy, Jean M. J. Fréchet, Paul Chang, Josephine Lee, and Vivek Subramanian,Organic Thin Film Transistors from a Soluble Oligothiophene Derivative Containing Thermally Removable Solubilizing Groups [J. Am. Chem. Soc. 2004, 126, 1596-1597]. J. Am. Chem. Soc.; 2004; 126(37) pp. 1750-11750.
Zhiyong Luo, John Williams, Roger W. Read, and Dennis P. Curran,Fluorous Boc(Boc)Carbamates: New Amine Protecting Groups for Use in Fluorous Synthesis, J. Org. Chem.; 2001; 66(12) pp. 4261-4266.
John D. Bass and Alexander Katz,Thermolytic Synthesis of Imprinted Amines in Bulk Silica, Chem. Mater.; 2003; 15(14) pp. 2757-2763.
David Mecerreyes, Hans Grande, Oscar Miguel, Estibalitz Ochoteco, Rebeca Marcilla, and Igor Cantero,Porous Polybenzimidazole Membranes Doped with Phosphoric Acid: Highly Proton-Conducting Solid Electrolytes, Chem. Mater.; 2004; 16(4) pp. 604-607.
Wainright, J.S., Wang, J-T., Weng, D., Savinell, R.F., and M.H. Litt, “Acid-Doped Polybenzimidazoles. A New Polymer Electrolyte,” J. Electrochem. Soc., 142, L121-L123 (1995).
B. Xing and O. Savadogo, J. New. Mat. Electrochem. Systems 2, 95 (1999).
Jones Michael G.
Klaehn John R.
Luther Thomas A.
Orme Christopher J.
Peterson Eric S.
Battelle Energy Alliance, LLC
Truong Duc
Wells St. John P.S.
LandOfFree
Polybenzimidazole compounds, polymeric media, and methods of... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Polybenzimidazole compounds, polymeric media, and methods of..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Polybenzimidazole compounds, polymeric media, and methods of... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3860164