Parylene variants and methods of synthesis and use

Organic compounds -- part of the class 532-570 series – Organic compounds – Halogen containing

Reexamination Certificate

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C570S144000, C570S184000

Reexamination Certificate

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07994372

ABSTRACT:
Fluorinated paracyclophane compounds represented by the formula:where least one of R1 and R2 comprises a fluorinated moiety is disclosed. These compounds can be utilized as precursor dimer compounds to produce polymeric coatings comprising copolymers of trifluorinated paraxylylene, including flexible fluorinated paraxylylene coatings.

REFERENCES:
patent: 3246627 (1966-04-01), Loeb et al.
patent: 3268599 (1966-08-01), Chow
patent: 3274267 (1966-09-01), Sui-Wu
patent: 3280202 (1966-10-01), Glich
patent: 3297591 (1967-01-01), Chow et al.
patent: 3301707 (1967-01-01), Loeb et al.
patent: 3332891 (1967-07-01), Chow
patent: 3342754 (1967-09-01), Gorham
patent: 3405117 (1968-10-01), Yeh
patent: 3749601 (1973-07-01), Tittle
patent: 4176209 (1979-11-01), Baker et al.
patent: 4429153 (1984-01-01), Punja
patent: 4734503 (1988-03-01), Weigert
patent: 4734533 (1988-03-01), Ungarelli et al.
patent: 4761269 (1988-08-01), Conger et al.
patent: 4783561 (1988-11-01), Pregaglia et al.
patent: 4795838 (1989-01-01), Bornengo et al.
patent: 4816608 (1989-03-01), Bornengo et al.
patent: 4846998 (1989-07-01), Pohl et al.
patent: 4853488 (1989-08-01), Ungarelli et al.
patent: 4886923 (1989-12-01), Ungarelli et al.
patent: 4924014 (1990-05-01), Fuss et al.
patent: 5069972 (1991-12-01), Versic
patent: 5094906 (1992-03-01), Witzke et al.
patent: 5210341 (1993-05-01), Dolbier, Jr. et al.
patent: 5266349 (1993-11-01), Bok et al.
patent: 5268202 (1993-12-01), You et al.
patent: 5288504 (1994-02-01), Versic
patent: 5302767 (1994-04-01), Galley et al.
patent: 5310858 (1994-05-01), Greiner et al.
patent: 5368645 (1994-11-01), Bok et al.
patent: 5424097 (1995-06-01), Olson et al.
patent: 5534068 (1996-07-01), Beach et al.
patent: 5536317 (1996-07-01), Crain et al.
patent: 5536319 (1996-07-01), Wary et al.
patent: 5536321 (1996-07-01), Olsen et al.
patent: 5536322 (1996-07-01), Wary et al.
patent: 5536892 (1996-07-01), Dolbier, Jr. et al.
patent: 5538758 (1996-07-01), Beach et al.
patent: 5556473 (1996-09-01), Olson et al.
patent: 5669971 (1997-09-01), Bok et al.
patent: 5689027 (1997-11-01), Abichandani et al.
patent: 5709753 (1998-01-01), Olson et al.
patent: 5789068 (1998-08-01), King et al.
patent: 5828132 (1998-10-01), Eissa
patent: 5841005 (1998-11-01), Dolbier, Jr. et al.
patent: 5849962 (1998-12-01), Dolbier, Jr. et al.
patent: 5879808 (1999-03-01), Wary et al.
patent: 5886026 (1999-03-01), Hunter et al.
patent: 5888905 (1999-03-01), Taylor et al.
patent: 5908506 (1999-06-01), Olson et al.
patent: 6030706 (2000-02-01), Eissa et al.
patent: 6130096 (2000-10-01), Tinker et al.
patent: 6150499 (2000-11-01), Dolbier, Jr. et al.
patent: 6184425 (2001-02-01), Kolomeitsev et al.
patent: 6245760 (2001-06-01), He et al.
patent: 6284933 (2001-09-01), Dolbier, Jr. et al.
patent: 6362115 (2002-03-01), Mandal
patent: 6380415 (2002-04-01), Uneyama et al.
patent: 6392097 (2002-05-01), Dolbier, Jr. et al.
patent: 6464740 (2002-10-01), Towery et al.
patent: 6549327 (2003-04-01), Foucher et al.
patent: 6559474 (2003-05-01), Craighead et al.
patent: 6602932 (2003-08-01), Feldheim et al.
patent: 6646150 (2003-11-01), Sato et al.
patent: 6667099 (2003-12-01), Greiner et al.
patent: 6723143 (2004-04-01), Towery et al.
patent: 6763576 (2004-07-01), Watchko et al.
patent: 6770789 (2004-08-01), Dolbier, Jr. et al.
patent: 6780561 (2004-08-01), Ueda et al.
patent: 6869698 (2005-03-01), Chen et al.
patent: 6919484 (2005-07-01), Dolbier, Jr. et al.
patent: 6943232 (2005-09-01), Blomquist et al.
patent: 7012165 (2006-03-01), Dolbier, Jr. et al.
patent: 7173159 (2007-02-01), Ho et al.
patent: 7462750 (2008-12-01), Hanefeld et al.
patent: 2002/0026086 (2002-02-01), Dolbier, Jr. et al.
patent: 2003/0165613 (2003-09-01), Chappa et al.
patent: 2003/0228411 (2003-12-01), Tai et al.
patent: 2006/0083770 (2006-04-01), Greiner et al.
patent: 2007/0009738 (2007-01-01), Kumar
patent: 2007/0099019 (2007-05-01), Hanefeld et al.
patent: 2007/0148390 (2007-06-01), Kumar
patent: 2007/0228606 (2007-10-01), Hanefeld et al.
patent: 1262817 (2002-12-01), None
patent: 09025252 (1997-01-01), None
patent: 2002080412 (2002-03-01), None
patent: 2005183729 (2005-07-01), None
patent: 9002604 (1990-03-01), None
patent: 9824743 (1998-06-01), None
patent: 9935111 (1999-07-01), None
patent: 03055611 (2003-07-01), None
patent: 03066933 (2003-08-01), None
patent: 2004065295 (2004-08-01), None
Chen, et al, “Surface Modification of Confined Microgeometries via Vapor-Deposited Polymer Coatings,” J.Am. Chem. Soc. 2006, 128, 374-380; rec'd Oct. 24, 2005 (XP-002591221).
4-trifluoroacetyl [2,2] paracyclophane, Database Beilstein, Beilstein Institute for Organic Chemistry, Frankfurt-Main, DE; 2001 (XP-002591222).
Reaction of [2,2] paracyclophane-1-carbaldehyde to 1-methyl [2,2] paracyclophane, Database Beilstein, Beilstein Institute for Organic Chemistry, Frankfurt-Main, DE; 1986 (XP-002591223).
Reaction of 1-methoycarbonyl [2,2] paracyclophane to 1-hydroxymethylene [2,2] paracyclophane, Database Beilstein, Beilstein Institute for Organic Chemistry, Frankfurt-Main, DE; 1972 (XP-002591224).
Ahvazi et al., F. Nuclear Magnetic Resonance Spectroscopy for the Elucidation of Carbonyl Groups in Lignins. 1. Model Compounds, J. Argic Food Chem. 1966, 44, 2167-2175.
Amii, The Catalytic Version of Stoichiometric Organic Synthesis, Department of Chemistry, Faculty of Science, Kobe University, Letters in Organic Chemistry, 2005, 2, 5-14.
Battiste, “4,5-Dehydrooctafluoro[2.2]paracyclophane:facile generation and extraordinary Diels-Alder reactivity,” Tetrahedron Letters, 43 (2002) 7047-7049.
Derwent Journal of Synthetic Methods, vol. 28, No. 11, 2002 Derwent Information.
Dolbier et al., An Unprecedented Photodimerization of an Anthraceno [2.2] Paracyclophane, Department of Chemistry, University of Florida, ARKIVOC 2006, p. 97-103.
Dolbier, Jr. et al., “Synthesis of Perfluoro[2.2]paracyclophane,” J. Org. Chem 2008, 73, pp. 2469-2472, (published on Web Feb. 27, 2008).
Dolbier, Jr. et al., Electronic Control of Stereoselectivities of Electrocyclic Reactions of Cyclobutenes: A Triumph of Theory in the Prediction of Organic Reactions, Acc. Chem. Res. 1996, 29, 471-477.
Dolbier et al., “A Novel, Non-High Dilution Method for Preparation of 1,1,2,2,9,9,10,10-Octafluoro[2.2] paracyclophane,” Organic Letters, 2000, 2(13), 1867-1869.
English Translation of Miki et al. (JP2002080412A), 2002.
Kale, Halogenation and Isomerization Reactions of Aromatics Over K-L, H-Beta and H-ZSM-5 Zeolite Catalysts, Catalysis Division, National Chemistry Laboratory, Pune 411 008, India, Apr. 2002.
Ligon, Jr. et al., First Separation and Characterization of CIS and Trans 1,2-Bisaryloxy Perfluorocyclobutanes, Journal of Fluorine Chemistry 123 (2003) p. 139-146.
Murakami, “Molecular recognition by novel cage-type azaparacyclophanes bearing chiral binding sites in aqueous media,” Pure & Appl. Chem. 65, 3, 551-556 (1993).
Plenio, The Coordination Chemistry of the CF Unit in Fluorocarbons, Chem Review, 1997, pp. 3363-3384.
Shioiri et al., “Use of the aryl groups as the carboxyl synthon. Application to the synthesis of some natural products containing hydroxyl amino acid functions,” Pure & Appl. Chem., vol. 66,, Nos. 10/11, pp. 2151-2154 (1994).
Solodukhin et al., Phenoxydifluoromethyl Substituted Nitrogen Heterocycles, Synthesis and Heterocyclization Reactions of Ethyl 4,4-Difluoro-4-Phenoxyacetoacetate, Molecules 2004, p. 9, 164-169.
“Solvent Resistance of the Parylene,” Abstract, 2001, 8 pages, Specialty Coating Systems, Indianapolis, IN (2001).
Wenk et al., Matrix Isolation and Photochemistry of Tetrafluoro-P-Xylylene, Eur. J. Org. Chem. 1999, pp. 3287-3290.
Wolgemuth, “Assessing the Performance and Suitability of Parylene Coating,” Medical Device & Diagnostic Industry Magazine MDDI Article Index, Aug. 2000, pp. 1-7.
Wolgemuth, “The Surface Modification Properties of Parylene for Medical Applications,” Business Briefing: Medical Device Manufacturing & Technology, 2002, pp. 1-4

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