Fluorine-containing Monomer Is A Ketone Or Aldehyde Patents (Class 526/244)
  • Patent number: 5616813
    Abstract: A novel bifunctional vinyl ether compound having an aromatic ring, represented by the following general formula: ##STR1## where X is a halogen atom and n is an integer of 1 to 5, effective as a copolymer component for fluorine-containing elastomers is produced by adding a chlorine atom or a bromine atom (Y) to CF.sub.2 .dbd.CFO(CF.sub.2)nCOOR, where R is a lower alkyl group, then subjecting the resulting CF.sub.2 YCFYO(CF.sub.2)nCOOR to hydrolysis and acid chloridation, followed by reaction with monohalogenobenzene, reaction with SF.sub.4 to convert --CO-- to --CF.sub.2 --, and dechlorination or debromination, or by subjecting CF.sub.2 .dbd.CFO (CF.sub.2)nCOOR to hydrolysis and acid chloridation, followed by reaction with monohalogenobenzene and reaction with SF, to convert --CO-- to --CF.sub.2 --.
    Type: Grant
    Filed: October 31, 1995
    Date of Patent: April 1, 1997
    Assignee: Nippon Mektron Limited
    Inventors: Cherstokov V. Filippovich, Sterlin S. Rafailovich, S. Lev German, deceased, Lin Jeng-Tain, Satoru Saito, Haruyoshi Tatsu
  • Patent number: 5614123
    Abstract: A textile treatment agent which contains, as an active component, a graft fluorocopolymer having a backbone of a polymer of a fluoromonomer and a branch of a polymer of a fluorine-free macromonomer prepared by copolymerizing the fluoromonomer with the macromonomer which is a fluorine-free macromonomer having addition-polymerizable unsaturated group at a molecular end gives excellent water- and oil-repellency and stainproof property.
    Type: Grant
    Filed: July 31, 1995
    Date of Patent: March 25, 1997
    Assignee: Daikin Industries Ltd.
    Inventors: Motonobu Kubo, Takashi Enomoto, Taro Sano, Kazunori Hayashi, Akihiko Ueda, Masamichi Morita
  • Patent number: 5540997
    Abstract: An alignment layer for a liquid crystal display device is described. The alignment layer comprises a copolymer of a thermoset polymer containing perfluorinated cyclobutane rings and a thermoplastic polymer containing perfluorinated cylcobutane rings, or a blend of thermoset and thermoplastic homopolymers or copolymers containing perfluorinated cyclobutane rings.This copolymer or blend provides an alignment layer with a cure temperature of less than 250.degree. C., a low dielectric, and a low moisture content. The resultant alignment layer can also provide surface tilt angles suitable for supertwisted nematic-liquid crystal displays.
    Type: Grant
    Filed: March 13, 1995
    Date of Patent: July 30, 1996
    Assignee: The Dow Chemical Company
    Inventors: Donald J. Perettie, Benjamin M. DeKoven, David A. Babb
  • Patent number: 5442021
    Abstract: Luminescent copolymers having the following structure:[A].sub.a --[B].sub.bin whichA is a luminescent component,B represents (co)monomers anda and b represent the percentages by weight of A and B in the copolymer, a making up 0.0001 to 20% by weight and b making up 99.9999 to 80% by weight, rare earth metal complexes having the formula M.sup.3+ (L).sub.n --suitable as component A in claim 1--where M.sup.3+ is the cation of a rare earth metal, L is a polymerizable complex ligand and n is an integer of 1 to 4, as their initial product and the use of the luminescent copolymers in medical diagnosis.
    Type: Grant
    Filed: February 18, 1994
    Date of Patent: August 15, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventor: Ludger Heiliger
  • Patent number: 5426164
    Abstract: A polymer has at least one photoactive site and more than one perfluorocyclobutane group. New monomers containing photoactive sites or photoactive precursors and at least one perfluorovinyl group are useful for making such polymers. Processes of making such polymers and the monomers from which they are made are disclosed. The polymers are useful in coatings, photoresists, and the like.
    Type: Grant
    Filed: December 24, 1992
    Date of Patent: June 20, 1995
    Assignee: The Dow Chemical Company
    Inventors: David A. Babb, W. Frank Richey, Katherine S. Clement, Eric S. Moyer, Marius W. Sorenson
  • Patent number: 5409777
    Abstract: A laminate has at least two layers, at least one of which comprises a polymer having more than one perfluorocyclobutane group. Such polymers impart qualities of enviornmental or protection, chemical and solvent resistance, hydrolytic stability, lubricity, low dielectric, hydrostatic stability, weatherability, flame resistance, chemical resistance, hydrolytic stability, lubricity, environmental protection, scratch resistance, solvent resistance, surface passivation, water repellancy, lower surface refractive index, lower surface coefficient of friction, fluid barrier properties, oil repellancy, thermal stability, and/or reduced moisture pick-up. Additionally, the coatings are optically clear, easy to apply either neat, in a solvent or otherwise, have relatively low cure temperatures for their temperature resistance, and exhibit insulating and planarizing capabilities.
    Type: Grant
    Filed: June 15, 1993
    Date of Patent: April 25, 1995
    Assignee: The Dow Chemical Company
    Inventors: Alvin P. Kennedy, Larry D. Bratton, Zdravko Jezic, Eckel R. Lane, Donald J. Perettie, W. Frank Richey, David B. Babb, Katherine S. Clement
  • Patent number: 5364917
    Abstract: A process for preparing a polymer having perfluorocyclobutane rings by the steps of (a) contacting monomers having aromatic polyester, aromatic polyamide, or polyimide groups or combination thereof, at least two dimerizable perfluorovinyl groups; and (b) exposing the monomers to sufficient heat and for a sufficient time that a polymer containing perfluorocyclobutane rings is formed. Chain extending oligomers of polymers having poor processing characteristics by this process results in polymers which are more easily processed. For instance, perfluorocyclobutane groups formed in an extruder to chain lengthen polyimide oligomers, in effect, render polyimides extrudable. The polymer formed by the method preferably has polyimide groups. New monomers and polymers having imide and perfluorovinyl or perfluorocyclobutane structures, respectively, are prepared.
    Type: Grant
    Filed: December 1, 1993
    Date of Patent: November 15, 1994
    Assignee: The Dow Chemical Company
    Inventors: David A. Babb, W. Frank Richey, Katherine S. Clement, Bobby R. Ezzell
  • Patent number: 5364547
    Abstract: A new lubricant comprises at least one compound having a perfluorocyclobutane group, preferably a perfluorovinyl aryl ether. The lubricant is conveniently applied from solvents which are not chlorofluorocarbons and is effective at high temperatures e.g., in engines and for magnetic media, either internally or topically.
    Type: Grant
    Filed: April 26, 1993
    Date of Patent: November 15, 1994
    Assignee: The Dow Chemical Company
    Inventors: David A. Babb, Ted A. Morgan
  • Patent number: 5284902
    Abstract: The present invention comprises a flourochemical composition exhibiting water and oil repellency properties which is soluble in an a hydrocarbon solvent system which is non-halogenated or substantially free of halogens and strong carbonyl solvents.
    Type: Grant
    Filed: January 3, 1992
    Date of Patent: February 8, 1994
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Charles D. Huber, Richard J. Grant, Richard S. Smith
  • Patent number: 5247035
    Abstract: At least 95% tetrahydrofuran soluble polymers are obtainable by copolymerization of a monomer mixture ofA) from 1 to 99% by weight of at least one at least 98% pure monomer of the general formula ICH.sub.2 .dbd.C(E)CH.sub.2 --O--CH.sub.2 C(E').dbd.CH.sub.2 Iwhere E and E' have been selected from the group consisting of --COOR.sup.1, --COR.sup.1, --CONR.sup.2 R.sup.3 and --CN and R.sup.1, R.sup.2 and R.sup.3 are each defined as follows:R.sup.1 =H, alkyl, cycloalkyl, cycloalkylalkyl, wherein the cycloalkyl rings may be alkyl- or alkoxy-monosubstituted, -disubstituted or -trisubstituted, hydroxyalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, aryl, arylalkyl, wherein the aryl groups may carry up to three of the following groups: halogen, alkyl, alkoxy, carboxyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, nitrilo, nitro, amino, alkylamino, dialkylamino;R.sup.2, R.sup.
    Type: Grant
    Filed: January 19, 1993
    Date of Patent: September 21, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Siegmund Besecke, Andreas Deckers, Harald Lauke
  • Patent number: 5212269
    Abstract: Processible chromophoric polymers having nonlinear optical properties and wherein the chromophore is present in and is a part of the polymer backbone, including substantially all of the monomer or repeat units, with the dipole moments pointing in the same direction (head-to-tail) along the polymer backbone. Such polymers include phenylene, phenylene vinylene, stilbenylene, phenyl piperdine, and coumarin polymers.
    Type: Grant
    Filed: March 25, 1991
    Date of Patent: May 18, 1993
    Inventors: John Fischer, Ronald Henry, James Hoover, Geoffrey Lindsay, John Stenger-Smith, Andrew P. Chafin
  • Patent number: 5198513
    Abstract: A compound having at least one perfluorovinyl group and at least one functional group is suitable for reacting with and/or forming polymers. The compound is preferably of Formula I:(G)n-R-(X--CF.dbd.CF.sub.2).sub.mwherein R represents an optionally substituted hydrocarbyl group, X represents any group which links R and a perfluorovinyl group; n is the number of G groups, m is the number of (XCF.dbd.CF.sub.2) groups; and G represents any reactive functional group or a group convertible into a reactive functional groups.A process for preparing a compound of Formula I comprises the steps of:(a) preparing a 2-halotetrafluoro compound of the Formula III:(Q--CF.sub.2 --CF.sub.2 -X).sub.m -R-(G").sub.
    Type: Grant
    Filed: March 12, 1991
    Date of Patent: March 30, 1993
    Assignee: The Dow Chemical Company
    Inventors: Katherine S. Clement, David A. Babb, Bobby R. Ezzell, W. Frank Richey
  • Patent number: 5162468
    Abstract: Compounds have a structure represented by Formula I:CF.sub.2 .dbd.CF--X--R--(X--CF.dbd.CF.sub.2).sub.mwherein R represents an unsubstituted or inertly substituted hydrocarbyl group; each X is independently selected from the group consisting of groups having at least one non-carbon atom between R and --CF.dbd.CF.sub.2 ; and m is an integer of from 1 to about 3. Polymers formed from such compounds are also prepared. The compounds are preferably prepared by a method by a process comprising the steps of:(a) forming a salt having anion corresponding to a compound of Formula II:HX--R--(XH.sub.m);wherein X, R and m are as defined for Formula I:(b) reacting the salt with a 1,2-dihalo-1,1,2,2-tetrafluoroethane wherein the halo groups are iodine, bromine, chlorine or mixtures thereof, at least one halo group being bromine or iodine, to form a compound of Formula III:Z--CF.sub.2 CF.sub.2 --X--R--(X--CF.sub.2 CF.sub.2 --Z).sub.
    Type: Grant
    Filed: March 12, 1991
    Date of Patent: November 10, 1992
    Assignee: The Dow Chemical Company
    Inventors: David A. Babb, Katherine S. Clement, Bobby R. Ezzell
  • Patent number: 5159038
    Abstract: A process for preparing a polymer having perfluorocyclobutane rings by the steps of (a) contacting monomers having at least two dimerizable perfluorovinyl groups; and (b) exposing the monomers to sufficient heat and for a sufficient time that a polymer containing perfluorocyclobutane rings is formed. The invention includes polymers having a backbone comprising hydrocarbyl groups, perfluorocyclobutane rings and non-carbon atoms and polymers of at least 10,000 molecular weight having repeating units [O-(CFR.sub.f).sub.n -O-perfluorocyclobutane].
    Type: Grant
    Filed: March 22, 1991
    Date of Patent: October 27, 1992
    Assignee: Dow Chemical Company
    Inventors: David A. Babb, W. Frank Richey, Katherine S. Clement, Bobby R. Ezzell
  • Patent number: 5159037
    Abstract: The present invention is a process for preparing a polymer having perfluorocyclobutane rings by the steps of (a) contacting monomers having at least two dimerizable perfluorovinyl groups; and (b) exposing the monomers to sufficient heat and for a sufficient time that a polymer containing perfluorocyclobutane rings is formed wherein at least about 0.05 mole percent of the monomer, have at least 3 dimerizable perfluorovinyl groups and polymers prepared thereby.
    Type: Grant
    Filed: June 25, 1991
    Date of Patent: October 27, 1992
    Assignee: The Dow Chemical Company
    Inventors: Katherine S. Clement, David A. Babb, Bobby R. Ezzell
  • Patent number: 5159036
    Abstract: A crosslinked polymer having perfluorocyclobutane rings is prepared in a process comprising the steps of: (a) contacting monomers having two dimerizable perfluorovinyl groups; (b) exposing the monomers to sufficient heat and for a sufficient time that a (linear) polymer containing perfluorocyclobutane rings is formed; and (c) exposing the polymer to sufficient crosslinking initiating means and for a sufficient time such that crosslinking occurs. Crosslinked polymers, so prepared are novel and have tensile strength and other physical properties enhanced over the properties of the corresponding linear polymer.
    Type: Grant
    Filed: March 22, 1991
    Date of Patent: October 27, 1992
    Assignee: The Dow Chemical Company
    Inventor: David A. Babb
  • Patent number: 5128386
    Abstract: UV-crosslinkable materials based on (meth)acrylate copolymers contain copolymerized monomers of the general formula I ##STR1## where R is a certain alkyl radical, an aryl radical or a radical R.sup.1 and R.sup.1 is a radical ##STR2## where R.sup.2 to R.sup.6 are each H, alkyl, a non-ortho OH group, OCH.sub.3, OC.sub.2 H.sub.3, SH, SCH.sub.3, Cl, F, CN, COOH, COO(C.sub.1 -C.sub.3 -alkyl), CF.sub.3, N(CH.sub.3).sub.2, N(C.sub.2 H.sub.5).sub.2, N(CH.sub.3)C.sub.6 H.sub.5, .sup.+ N(CH.sub.3).sub.3 X.sup.- or .sup.+N(CH.sub.3).sub.X X.sup.-, where X.sup.- is an acid anion, and one or more of the radicals R.sup.2 to R.sup.
    Type: Grant
    Filed: December 15, 1989
    Date of Patent: July 7, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Rehmer, Andreas Boettchher, Gerhard Auchter
  • Patent number: 5041510
    Abstract: This invention provides novel side chain copolymers which exhibit nonlinear optical response, and which have utility as a transparent optical component in all-optical and electrooptical light switch and light modulator devices.
    Type: Grant
    Filed: February 7, 1990
    Date of Patent: August 20, 1991
    Assignee: Hoechst Celanese Corp.
    Inventors: Diane Allen, Cherylyn Lee, Ronald N. DeMartino
  • Patent number: 4921923
    Abstract: Oligomeric condensation products of certain diketones and phenols can be end-capped with a vinylbenzyl moiety and certain other moieties, especially alkyl groups, to afford thermosetting resins particularly valuable in making laminated circuit boards. Resins prepared by the reaction of 1 molar proportion of diacetylbenzene with from 3.5 to 4.0 molar proportions of phenol and end-capped with from 50 to 100% vinylbenzyl groups with the remainder being alkyls of 1 through 11 carbon atoms are particularly useful.
    Type: Grant
    Filed: November 18, 1988
    Date of Patent: May 1, 1990
    Assignee: Allied Signal Inc.
    Inventors: Joseph J. Zupancic, Jean M. J. Frechet, Andrew M. Zweig, Jeffrey P. Conrad
  • Patent number: 4876322
    Abstract: Linear fluorooligomers having at least two reactive end groups per polymer molecule are incorporated into radiation sensitive polymer systems which have improved continuous temperature resistance and low dielectric constant. The polymer systems can be applied as lacquers. Preferably perfluorated poly-ethers and perfluorated alkanes are used as starting compounds. The polymeric product is usable as a coating for the production of printed multi-layer wirings and economises on through-bores and additional copper intermediate layers. A further field of application exists in the field of integrated semiconductor circuits in VLSI-technology for the production of negative photo-resists.
    Type: Grant
    Filed: September 4, 1987
    Date of Patent: October 24, 1989
    Assignee: Siemens Aktiengesselschaft
    Inventors: Klaus Budde, Friedrich Koch, Ferdinand Quella
  • Patent number: 4576752
    Abstract: .beta.-Substituted polyfluoroethyl compounds, process for the preparation thereof, copolymers thereof, compound intermediates, and process therefor. The copolymers are useful as ion exchange resins or structural foams.
    Type: Grant
    Filed: July 19, 1982
    Date of Patent: March 18, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Carl G. Krespan
  • Patent number: 4434273
    Abstract: Perfluoroketovinyl ether of the formula (as in claim 1) wherein n is an integer 1 to 4; copolymers of such ether and a fluorinated monomer, such as tetrafluoroethylene; ion-exchange resins of such copolymers; and ion-exchange membranes of such resins.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: February 28, 1984
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Ronald E. Uschold
  • Patent number: 4424325
    Abstract: A copolymer comprising (a) a monomer having a C.sub.7 to C.sub.21 perfluoroalkyl or perfluoroalkenyl group at one end of the molecule and an ethylenically unsaturated group at the other end of the molecule, and (b) a monomer having a photosensitive group, e.g. an azidobenzoyloxy group, cinnamoyloxy group, benzoylphenyl group or .alpha.,.beta.-unsaturated ketone group. The copolymer has an excellent photosensitivity and excellent water and oil repellent properties, and is useful for various purposes, e.g. as a photosensitive material for dry offset printing plate or resist and as a photo-curable, water and oil repelling coating material.
    Type: Grant
    Filed: May 20, 1981
    Date of Patent: January 3, 1984
    Assignee: Daikin Kogyo Co., Ltd.
    Inventors: Takahiro Tsunoda, Tsuguo Yamaoka, Sinji Tamura
  • Patent number: 4335255
    Abstract: Ketoester of the formula ##STR1## .alpha.-carboxylate-.omega.-acyl fluoride of the formula ##STR2## vinyl ether of the formula ##STR3## divinyl ether of the formula ##STR4## allyl ether of the formula ##STR5## and film-forming copolymers, useful as molding resins, of the vinyl ether and/or the divinyl ether or the allyl ether and a fluorinated vinyl monomer, for example, tetrafluoroethylene, wherein, in the above formulas, n is 0 to 6, p is 0 to 7, X is CO.sub.2 M, CO.sub.2 R, CO.sub.2 H, CONH.sub.2, COF, COCl or CN, M is alkali metal, ammonium or quaternary ammonium and R is C.sub.1-8 alkyl, selected copolymers, after hydrolysis, being water-wettable and dyeable, exhibiting ion-exchange properties and being useful in curable fluoroelastomer compositions and, in film form, as the membrane in a chloroalkali electrolysis cell.
    Type: Grant
    Filed: April 3, 1980
    Date of Patent: June 15, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Carl G. Krespan
  • Patent number: 4292449
    Abstract: The reaction of a polyfluorocarbonyl compound such as a polyfluoroketone or polyfluorocarboxylic acid fluoride with fluoride ion and a polyfluoroallyl chloride, bromide or fluorosulfate produces a polyfluoroallyloxy compound, e.g., CF.sub.2 .dbd.CFCF.sub.2 OCF.sub.2 CF.sub.3. The polyfluoroallyloxy compounds copolymerize with ethylenically unsaturated monomers such as tetrafluoroethylene, chlorotrifluoroethylene or vinylidene fluoride to form polymers which are moldable, and in some cases electrically conducting or are water-wettable and dyeable.
    Type: Grant
    Filed: May 1, 1980
    Date of Patent: September 29, 1981
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Carl G. Krespan
  • Patent number: 4275225
    Abstract: The reaction of a polyfluorocarbonyl compound such as a polyfluoroketone or polyfluorocarboxylic acid fluoride with fluoride ion and a polyfluoroallyl chloride, bromide or fluorosulfate produces a polyfluoroallyloxy carboxylic acid or ester, e.g., CF.sub.2 .dbd.CFCF.sub.2 OCF.sub.2 CF.sub.2 COOH. The polyfluoroallyloxy compounds copolymerize with ethylenically unsaturated monomers such as tetrafluoroethylene, chlorotrifluoroethylene or vinylidene fluoride to form polymers which are moldable, and in some cases electrically conducting or are water-wettable and dyeable.
    Type: Grant
    Filed: May 1, 1980
    Date of Patent: June 23, 1981
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Carl G. Krespan
  • Patent number: 4273728
    Abstract: The reaction of a polyfluorocarbonyl compound such as a polyfluoroketone or polyfluorocarboxylic acid fluoride with fluoride ion and a polyfluoroallyl chloride, bromide or fluorosulfate produces a polyfluoroallyloxy compound, e.g., CF.sub.2 .dbd.CFCF.sub.2 OCF.sub.2 CF.sub.2 CN. The polyfluoroallyloxy compounds copolymerize with ethylenically unsaturated monomers such as tetrafluoroethylene, chlorotrifluoroethylene or vinylidene fluoride to form polymers which are moldable, and in some cases electrically conducting or are waterwettable and dyeable.
    Type: Grant
    Filed: May 1, 1980
    Date of Patent: June 16, 1981
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Carl G. Krespan
  • Patent number: 4225692
    Abstract: Disclosed are electron acceptor monomers of the formula: ##STR1## wherein R is ##STR2## R' is hydrogen or methyl; X and Y are independently selected from the group consisting of --NO.sub.2, halogen, cyano and --CF.sub.3 ;Z is oxygen or dicyanomethylene; anda and b can range from 0 to 3; with the proviso that at least one of R is ##STR3## and polymers prepared therefrom. These monomers and polymers are suitable for use in electrophotographic devices and methods.
    Type: Grant
    Filed: May 4, 1977
    Date of Patent: September 30, 1980
    Assignee: Xerox Corporation
    Inventor: Sam R. Turner
  • Patent number: 4172933
    Abstract: Disclosed are monomers of the formula: ##STR1## wherein R is ##STR2## R' is hydrogen or methyl; R" is alkyl of 1-10 carbon atoms;X and Y are independently selected from the group consisting of NO.sub.2, halogen, cyano and --CF.sub.3 ;Z is oxygen or dicyanomethylene;A and a' can range from 0-3; andN is 1-10.These monomers can be readily polymerized to polymers suitable for use in electophotographic imaging members and methods.
    Type: Grant
    Filed: May 23, 1977
    Date of Patent: October 30, 1979
    Assignee: Xerox Corporation
    Inventor: Sam R. Turner
  • Patent number: 4143225
    Abstract: Disclosed are monomers of the formula: ##STR1## WHEREIN R is ##STR2## R' is hydrogen or methyl; R" is alkyl of 1-10 carbon atoms;X and Y are independently selected from the group consisting of NO.sub.2, halogen, cyano and --CF.sub.3 ;Z is oxygen or dicyanomethylene;a and a' can range from 0-3; andn is 1-10.These monomers can be readily polymerized to polymers suitable for use in electrophotographic imaging members and methods.
    Type: Grant
    Filed: May 23, 1977
    Date of Patent: March 6, 1979
    Assignee: Xerox Corporation
    Inventor: Sam R. Turner