Fluorine Containing Monomer Contains At Least One Diverse Halogen Atom Patents (Class 526/249)
  • Patent number: 5877267
    Abstract: A method for polymerizing fluorine-containing ethylenically-unsaturated monomer and allylic-hydrogen containing olefin monomer is provided. The method involves the use of fluoroaliphatic-group containing sulfinate. Novel polymers are also disclosed, comprising interpolymerized units derived from tetrafluoroethylene and allylic-hydrogen containing olefin, for example, propylene.
    Type: Grant
    Filed: January 10, 1997
    Date of Patent: March 2, 1999
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Michael P. Greuel, Werner M. Grootaert
  • Patent number: 5863657
    Abstract: An adhesive for bonding together a first substrate made of vinylidene fluoride resin and a second substrate comprises an elastic fluorohydrocarbon resin, a polyisocyanate, and an organic solvent. This elastic fluorohydrocarbon resin is obtained by graft copolymerization of a fluorine-containing copolymer with a vinylidene fluoride monomer. This copolymer is prepared by copolymerizing at least one first fluorine-containing monomer with at least one unsaturated monomer that has peroxy bond. The adhesive itself is superior in durability, and bond strength between the first and second substrates is also superior.
    Type: Grant
    Filed: December 27, 1995
    Date of Patent: January 26, 1999
    Assignee: Central Glass Company, Limited
    Inventors: Chikashi Kawashima, Katunori Kawamura
  • Patent number: 5859123
    Abstract: The present invention relates to a water-based fluorine-containing emulsion. This emulsion contains a fluorine-containing copolymer in a disperse phase thereof This copolymer is prepared by copolymerizing: (A) a fluoroolefin, (B) an organosilicon compound containing an olefinic unsaturated bond and an alkoxysilyl group, (C) an unsaturated carboxylic acid represented by a general formula of CH.sub.2 .dbd.CH--(CH.sub.2).sub.n --COOH where n is an integer of from 3 to 15, and (D) at least one other copolymerizable monomer. A paint prepared from the emulsion is superior in storage stability and mechanical stability, although this paint belongs to a one-package paint. A coated film formed by applying the paint is superior in water resistance in its early stages, stain resistance, and weather resistance.
    Type: Grant
    Filed: November 15, 1996
    Date of Patent: January 12, 1999
    Assignee: Central Glass Company, Limited
    Inventors: Satoru Kobayashi, Kazuhiko Maeda, Yoshi Hirashima, Seiji Hasegawa, Kentaro Tsutsumi
  • Patent number: 5852125
    Abstract: The present invention relates to a new fluororubber, a process for its production and its use, as well as a process for producing fluororubber mouldings and/or coatings.
    Type: Grant
    Filed: May 30, 1997
    Date of Patent: December 22, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ralf Kruger, Jurgen Ackermann, Dieter Wrobel, Helmut Steinberger
  • Patent number: 5852150
    Abstract: Disclosed herein are copolymers of tetrafluoroethylene and n-alkyl trifluorovinyl ether which further contain either curesite repeat units and/or iodine. Such curesite repeat units, upon exposure to free radicals, may crosslink the copolymers. The iodine is introduced by carrying out free radical polymerization in the presence of an organic iodide chain transfer agent. The polymers according to the invention are especially useful as elastomers and/or as molding resins for articles or parts that may be exposed to a basic environment. The preparation of such polymers by aqueous emulsion polymerization is also disclosed.
    Type: Grant
    Filed: December 3, 1997
    Date of Patent: December 22, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Paul Gregory Bekiarian
  • Patent number: 5833070
    Abstract: A stretched PCTFE (polychlorotrifluoroethylene) film is provided with a good moisture-proofness (low moisture permeability) even at a relatively small thickness and at a small crystallinity The film is characterized by a crystallinity A (%) of 15-75% and a moisture permeability B (mg/m.sup.2.day) at a film thickness of 20 .mu.m, satisfying a relationship of B/(100-A).ltoreq.3.0. The film may suitably be produced through a process characterized by a sequence of a relatively low-temperature melt-extrusion and a low temperature stretching. The film is suitably used for constituting moisture-proof packaged products, such as an EL device or a packaged drug product.
    Type: Grant
    Filed: June 2, 1997
    Date of Patent: November 10, 1998
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Toshiya Mizuno, Yoshikichi Teramoto, Yasuhiro Tada
  • Patent number: 5773480
    Abstract: Polymeric compositions are derived from copolymers of .alpha.,.beta.,.beta.-trifluorostyrene with a variety of substituted .alpha.,.beta.,.beta.-trifluorostyrenes. These compositions are suitable for use as membranes, particularly as ion-exchange membranes, and most particularly as solid polymer electrolytes in electrochemical applications, such as, for example, electrochemical fuel cells.
    Type: Grant
    Filed: December 18, 1996
    Date of Patent: June 30, 1998
    Assignee: Ballard Power Systems Inc.
    Inventors: Charles Stone, Alfred E. Steck, Jinzhu Wei
  • Patent number: 5731394
    Abstract: Polytetrafluoroethylene (PTFE) fine powder is provided which exhibits both low rheometer extrusion pressure and high adhesion to wire by incorporating into the free powder the combination of perfluoro(alkyl) ethylene such as perfluoro(n-butyl) ethylene with fluoro(alkyl vinyl ether), such as perfluoro(propyl vinyl ether), or fluoroolefin such as hexafluoropropylene as modifiers of the PTFE fine powder. The modified PTFE fine powder is made by aqueous dispersion copolymerization of TFE with the modifying monomers, with the addition of molecular weight reducing agent towards the end of the polymerization reaction.
    Type: Grant
    Filed: March 27, 1997
    Date of Patent: March 24, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Theodore Arthur Treat, Satish Chandra Malhotra
  • Patent number: 5688838
    Abstract: Process for preparing hydrogen-containing fluoropolymers, wherein the corresponding olefinic monomers are (co) polymerized in an organic suspending medium in the presence of a radical photoinitiator and of ultraviolet-visible radiation at a temperature of from -60.degree. C. to +30.degree. C. Hydrogen-containing fluoropolymers are thus obtained having high second melting temperature and high maximum operating temperature, using as initiators non-hazardous products, which can be easily handled and kept also at room temperature.
    Type: Grant
    Filed: July 28, 1995
    Date of Patent: November 18, 1997
    Assignee: Ausimont S.p.A.
    Inventors: Julio A. Abusleme, Pier Antonio Guarda, Ralph De Pasquale
  • Patent number: 5674959
    Abstract: New fluoroelastomers are described, having iodine atoms in terminal position and monomeric units in the chain deriving from an iodinated olefin of formula:CHR.dbd.CH--Z--CH.sub.2 CHR--I (I)wherein: R is --H or --CH.sub.3 ; Z is a (per)fluoroalkylene radical C.sub.1 -C.sub.18, linear or branched, optionally containing one or more ether oxygen atoms, or a (per) fluoropolyoxyalkylene radical.These products, upon peroxide curing, require extremely short post-curing treatments (around 30-60 minutes at 180.degree.-230.degree. C.) and are characterized by compression set values lower than 25% (measured on O-rings at 200.degree. C. for 70 hours according to ASTM Standard D395 Method B).
    Type: Grant
    Filed: October 1, 1996
    Date of Patent: October 7, 1997
    Assignee: Ausimont S.p.A.
    Inventors: Vincenzo Arcella, Giulio Brinati, Margherita Albano, Vito Tortelli
  • Patent number: 5670593
    Abstract: To provide a fluorine-containing olefin represented, for example, by CH.sub.2 .dbd.CFCF.sub.2 --R.sub.f.sup.6 --(CH.sub.2).sub.k --X.sup.2 ?wherein, X.sup.2 is --CH.sub.2 OH, ##STR1## or ##STR2## R.sub.f.sup.6 is a fluorine-substituted fluorine-containing alkyl group having 1 to 40 carbon atoms or --OR.sub.f.sup.7 -- (Rf.sup.7 is a fluorine-substituted fluorine-containing alkyl group having 1 to 40 carbon atoms or a fluorine-substituted fluorine-containing ether group having 3 to 50 carbon atoms), k is 0 or an integer of 1 to 6!; a fluorine-containing polymer with functional group which is prepared by polymerizing the above-mentioned olefin, has good affinity with various heat-resisting thermoplastic resins and is capable of forming homogeneous dispersion with the thermoplastic resin; and a thermoplastic resin composition comprising the above-mentioned fluorine-containing polymer with functional group and an aromatic polyester or the like as the heat-resisting thermoplastic resin.
    Type: Grant
    Filed: February 9, 1996
    Date of Patent: September 23, 1997
    Assignee: Daikin Industries, Ltd.
    Inventors: Takayuki Araki, Tetsuo Shimizu, Takafumi Yamato, Masahiro Kumegawa, Yoshihisa Yamamoto
  • Patent number: 5641571
    Abstract: Polytetrafluoroethylene micropowders, which can contain up to about 3% by weight of comonomers, are obtained with a narrow molecular weight distribution, a narrow range of specific surface area and a primary particle size of from 150 to 250 nm by polymerization in aqueous medium using hydrogen, methane or ethane as chain transfer agent and at an availability of free radicals remaining essentially constant over the polymerization time. These micropowders are particularly suitable for preparations of polyacetals which give only small deposits in the molds during melt processing and have increased color stability.
    Type: Grant
    Filed: October 5, 1995
    Date of Patent: June 24, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ludwig Mayer, Kai-Uwe Tonnes, Hermann Bladel
  • Patent number: 5639838
    Abstract: Fluoroelastomers comprising, by mole:(a) from 33 to 75% of tetrafluoroethylene (TFE);(b) from 15 to 45% of a perfluorovinylether (PVE);(c) from 10 to 22% of vinylidene fluoride (VDF).They are endowed with high resistance to polar solvents and to bases, excellent compression set also at high temperatures, low Tg and good processability.They result particularly suitable for the manufacture of sealing elements (O-rings) for plants intended to the production of methylterbutylether (MTBE).
    Type: Grant
    Filed: August 23, 1995
    Date of Patent: June 17, 1997
    Assignee: Ausimont S.p.A.
    Inventors: Margherita Albano, Vincenzo Arcella, Graziella Chiodini, Anna Minutillo
  • Patent number: 5639837
    Abstract: Disclosed herein is a process in which fluorine containing olefins are polymerized using an initiation system which is a combination of a fluoroaliphatic sulfinate or sulfinic acid and chlorate, bromate or hypochlorite ions. The resulting polymer contains fewer deleterious end groups and is more stable and/or easier to process. The polymers produced are useful as thermoplastics and elastomers.
    Type: Grant
    Filed: June 4, 1996
    Date of Patent: June 17, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: William Brown Farnham, Andrew Edward Feiring, Bruce Edmund Smart, Robert Clayton Wheland
  • Patent number: 5625019
    Abstract: New fluoroelastomers are described, having iodine atoms in terminal position and monomeric units in the chain deriving from an iodinated olefin of formula:CHR.dbd.CH--Z--CH.sub.2 CHR--I (I)wherein: R is --H or --CH.sub.3 ; Z is a (per)fluoroalkylene radical C.sub.1 -C.sub.18, linear or branched, optionally containing one or more ether oxygen atoms, or a (per)fluoropolyoxyalkylene radical.These products, upon peroxide curing, require extremely short post-curing treatments (around 30-60 minutes at 180.degree.-230.degree. C.) and are characterized by compression set values lower than 25% (measured on O-rings at 200.degree. C. for 70 hours according to ASTM Standard D395 Method B).
    Type: Grant
    Filed: May 15, 1995
    Date of Patent: April 29, 1997
    Assignee: Ausimont S.p.A.
    Inventors: Vincenzo Arcella, Giulio Brinati, Margherita Albano, Vito Tortelli
  • Patent number: 5623038
    Abstract: A method for polymerizing fluorine-containing ethylenically-unsaturated monomer and allylic-hydrogen containing olefin monomer is provided. The method involves the use of fluoroaliphatic-group containing sulfinate. Novel polymers are also disclosed, comprising interpolymerized units derived from tetrafluoroethylene and allylic-hydrogen containing olefin, for example, propylene.
    Type: Grant
    Filed: May 8, 1995
    Date of Patent: April 22, 1997
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Michael P. Greuel, Werner M. Grootaert
  • Patent number: 5621057
    Abstract: Alkenyl ether-siloxane compositions comprising(A) an oligomeric or polymeric organosilicon compound having on average more than one alkenyloxy group of the formulaR.sup.2 --CH.dbd.CH--O-- (VI)(B) a monomeric maleic and/or fumaric acid compound of the formula ##STR1## in which R.sup.2 is a hydrogen atom or the methyl radical,R.sup.3 is identical or different and is a hydrogen atom, a hydrocarbon radical having 1 to 16 carbon atoms, which can be interrupted by oxygen, sulfur or oxygen- or silicon-containing units, a substituted hydrocarbon radical having 1 to 6 carbon atoms, a silyl radical or a siloxanyl radical,R.sup.4 is identical or different and is a hydrogen atom, chlorine, bromine, fluorine or an optionally substituted alkyl radical andZ is an oxygen atom or a radical --NR.sup.5 --, where R.sup.5 has one of the meanings given for R.sup.3,optionally(C) initiators which form free radicals and optionally(D) inhibitors for regulating the pot life.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: April 15, 1997
    Assignee: Wacker-Chemie GmbH
    Inventors: Christian Herzig, Bernward Deubzer, Martina Bloechl, David Huettner, Walter Magee
  • Patent number: 5618894
    Abstract: The present invention provides a process for making fluorinated polymers and copolymers having stable end groups. The process includes (1) contacting a fluoromonomer, an initiator capable of producing stable end groups on the polymer chain, and a polymerization medium comprising carbon dioxide, and (2) polymerizing the fluoromonomer. The polymerization medium preferably comprises liquid or supercritical carbon dioxide. Advantageously, the process may also include the step of separating the fluoropolymer from the polymerization medium.The present invention also provides polymerization reaction mixtures useful in the processes of the present invention.
    Type: Grant
    Filed: June 1, 1995
    Date of Patent: April 8, 1997
    Assignee: The University of North Carolina
    Inventors: Joseph M. DeSimone, Timothy Romack
  • Patent number: 5602185
    Abstract: Sulfonyl fluoride substituted .alpha.,.beta.,.beta.-trifluorostyrene monomers are disclosed. The monomers are incorporated into polymeric compositions which are conveniently hydrolyzed to produce polymeric compositions which include ion-exchange moieties. The resulting compositions which include ion-exchange moieties are particularly suitable for use as solid polymer electrolytes in electrochemical applications, such as, for example, electrochemical fuel cells.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: February 11, 1997
    Assignee: Ballard Power Systems Inc.
    Inventors: Charles Stone, Alfred E. Steck, Robert D. Lousenberg
  • Patent number: 5589557
    Abstract: Polymers and copolymers of one or more fluorinated dienes of structure CFX.sup.1 .dbd.CX.sup.2 --O--CX.sup.3 X.sup.4 --O--CX.sup.2 .dbd.CX.sup.1 F, wherein X.sup.1 and X.sup.2 are F, Cl or H, and X.sup.3 and X.sup.4 are F or CF.sub.3, wherein said dienes essentially form cyclic repetitive units, the comonomers used for preparing copolymers being ethylene unsaturated fluorinated compounds.Processes for preparing the fluorinated dienes having said structure which comprise the reaction in solution between one halogenated olefin and one hypofluorite CX.sup.3 X.sup.4 (OF).sub.2, wherein X.sup.3 and X.sup.4 are F or CF.sub.3, and the dehalogenation or dehydrohalogenation of the linear adduct between one hypofluorite molecule and two olefin molecules. The polymers and copolymers of the invention are particularly suitable for preparing coatings for applications at high temperatures.
    Type: Grant
    Filed: May 15, 1995
    Date of Patent: December 31, 1996
    Assignee: Ausimont, S.p.A.
    Inventors: Walter Navarrini, Vito Tortelli, Alessandro Zedda
  • Patent number: 5585449
    Abstract: New fluoroelastomers are described, comprising monomeric units deriving from a bis-olefin having general formula: ##STR1## wherein: R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, equal or different from each other, are H or alkyls C.sub.1 -C.sub.5 ; Z is an alkylene or cycloalkylene radical C.sub.1 -C.sub.18, linear or branched, optionally containing oxygen atoms, preferably at least partially fluorinated, or a (per)fluoropolyoxyalkylene radical.Such products are endowed with improved processability, especially during calendering of the vulcanization mixture, along with superior mechanical and workability properties during extrusion and injection molding, with a very good mold release.
    Type: Grant
    Filed: December 22, 1994
    Date of Patent: December 17, 1996
    Assignee: Ausimont S.p.A.
    Inventors: Vincenzo Arcella, Giulio Brinati, Margherita Albano, Vito Tortelli
  • Patent number: 5578689
    Abstract: Vinyl polymers, e.g., the homo- and copolyvinyl chlorides, are prepared in one or more stages, to a degree of conversion of at least 50%, by suspended emulsion polymerizing at least one vinyl monomer, e.g., vinyl chloride, said at least one monomer having dispersed therein finely divided droplets of an aqueous solution of at least one component of a polymerization initiating system, and wherein the amount of water in said aqueous solution constitutes at least 19%, and preferably at least 20% by weight of the at least one monomer.
    Type: Grant
    Filed: February 22, 1994
    Date of Patent: November 26, 1996
    Assignee: Atochem
    Inventors: Pierre Nogues, Francois Erard
  • Patent number: 5576381
    Abstract: Aqueous dispersions of fluoropolymers which are obtained by emulsion polymerization, are not processsable from the melt and form a film on sintering, which comprise a fluoropolymer A) having an average particle size (number average) of from 180 to 400 nm and a fluoropolymer B) having an average particle size which is lower by a factor of from about 0.3 to about 0.7, so that the total dispersion has a non-monomadal number distribution of the particle diameter, are suitable for soaking, impregnating or coating surfaces, for example of fibers or planiform articles of fibers or porous materials, in particular for coating fiberglass fabrics, and also for the formulation of metal coating systems.
    Type: Grant
    Filed: November 29, 1994
    Date of Patent: November 19, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hermann Bl adel, Bernd Felix, Klaus Hintzer, Gernot L ohr, Wolf D. Mitterberger
  • Patent number: 5569728
    Abstract: The invention relates to a (co)polymerization process in suspension for preparing hydrogen containing thermoplastic fluoropolymers, such as for instance ethylene/chlorotrifluoro-ethylene or ethylene/tetrafluoroethylene copolymers, or vinylidenefluoride homopolymers or copolymers, wherein bis-dichlorofluoroacetylperoxide (CFCl.sub.2 --CO--O).sub.2 (DCFAP) is used as polymerization initiator. From such process products endowed with high thermal stability, remarkably higher than that obtainable using bis-trichloroacetylperoxide (TCAP), are obtained.
    Type: Grant
    Filed: March 16, 1995
    Date of Patent: October 29, 1996
    Assignee: Ausimont, S.p.A.
    Inventors: Julio A. Abusleme, Piero Gavezotti
  • Patent number: 5518652
    Abstract: The invention relates to copolymers made from mono-reactive liquid and/or di-reactive liquid crystals which can be photopolymerized to form copolymers and to novel reactive liquid crystal compound having a nematic phase. Preferentially the reactive liquid crystal is polymerized while in the liquid crystal phase to produce an oriented birefringent polymer film. To do this, the reactive liquid crystal, in its nematic or smectic phase is aligned (by well known techniques such as rubbed polyimide, etc.) and the thin film containing a small amount of photoinitiator, is subjected to ultraviolet light whereupon it polymerizes into a thin, aligned polymer film.
    Type: Grant
    Filed: July 1, 1994
    Date of Patent: May 21, 1996
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Owain L. Parri, Ian Bonny, Ian V. E. Hassall, Mark J. Goulding, Simon Greenfield, Emma J. Brown, David Coates
  • Patent number: 5510435
    Abstract: Cyclopentanes alkyl-substituted with one or more C.sub.1 -C.sub.6 alkyls are used as chain transfer agents in (co)polymerization reactions carried out, either in suspension or in aqueous emulsion, at low temperatures, comprised between -30.degree. and +30.degree. C., for preparing thermoplastic hydrogen-containing fluoropolymers , such as for instance ethylene/chlorotrifluoroethylene and ethylene/tetrafluoroethylene copolymers, or homopolymers and copolymers of vinylidenefluoride. They are transfer agents having high efficiency, which are liquid and thus can be easily handled and dosed, non-toxic, yielding alkyl end groups of high thermal stability.
    Type: Grant
    Filed: March 16, 1995
    Date of Patent: April 23, 1996
    Assignee: Ausimont S.p.A.
    Inventors: Julio A. Abusleme, Sheldon J. Kirsch
  • Patent number: 5498639
    Abstract: Polymeric compositions are derived from copolymers of .alpha.,.beta., .beta.-trifluorostyrene with a variety of substituted .alpha.,.beta.,.beta.-trifluorostyrenes. These compositions are suitable for use as membranes, particularly as ion-exchange membranes, and most particularly as solid polymer electrolytes in electrochemical applications, such as, for example, electrochemical fuel cells.
    Type: Grant
    Filed: May 16, 1995
    Date of Patent: March 12, 1996
    Assignee: Ballard Power Systems Inc.
    Inventors: Jinzhu Wei, Charles Stone, Alfred E. Steck
  • Patent number: 5484867
    Abstract: A process for preparation of reactive polyhedral oligomeric silsesquioxanes and the subsequent synthesis of polysilsesquioxanes which produce high yield, tractable polymers containing silsesquioxane segments is provided. A trifunctional polyhedral oligomeric silsesquioxane of the formula Si.sub.7 R.sub.7 O.sub.9 (OA).sub.3 is corner capped by reacting it with a compound of the formula M-Z to form a polyhedral oligomeric silsesquioxane which can be reacted in various ways with oligomers, polymers, catalysts, or co-monomers to form polyhedral silsesquioxane polymers containing silsesquioxanes as pendant, block, or end group segments. The resulting polymers are essentially free of impurities and have controllable properties through the proper selection of the synthesis process and starting materials.
    Type: Grant
    Filed: June 1, 1994
    Date of Patent: January 16, 1996
    Assignees: The University of Dayton, The Regents of the University of California, The United States of America as represented by the Secretary of the Air Force
    Inventors: Joseph D. Lichtenhan, Jeffrey W. Gilman, Frank J. Feher
  • Patent number: 5453477
    Abstract: Process for the production of PCTFE homopolymer and/or copolymer resins by the use of an aqueous suspension system incorporating a redox initiator system which comprises t-butyl hydroperoxide and sodium metabisulfite to initiate the polymerization or copolymerization process. The process parameters may be controlled to provide a PCTFE homopolymer or copolymer resin having a desired target range of molecular weights. The process provides stable PCTFE polymer suspensions which exhibit a low tendency to coagulate and further exhibit good wettability of the homopolymer and copolymer particles, notably in the absence of soaps.
    Type: Grant
    Filed: March 7, 1994
    Date of Patent: September 26, 1995
    Assignee: AlliedSignal Inc.
    Inventors: Bryce C. Oxenrider, Frank Mares, Mo-Shu Yang
  • Patent number: 5434229
    Abstract: Branched aliphatic hydrocarbons, having from 6 to 25 carbon atoms and a ratio between the number of methyl groups and the number of carbon atoms higher than 0.5, are used in radical (co)polymerization processes of fluorinated olefinic monomers, optionally in association with non-fluorinated olefins, both in suspension and in aqueous emulsion. Such hydrocarbons are characterized, in the usual reaction conditions, by a chain transfer effect practically absent.
    Type: Grant
    Filed: February 23, 1994
    Date of Patent: July 18, 1995
    Assignee: Ausimont S.p.A.
    Inventors: Julio A. Abusleme, Guglielmo Gregorio
  • Patent number: 5422411
    Abstract: Polymeric compositions are derived from copolymers of .alpha.,.beta.,.beta.-trifluorostyrene with a variety of substituted .alpha.,.beta.,.beta.-trifluorostyrenes. These compositions are suitable for use as membranes, particularly as ion-exchange membranes, and most particularly as solid polymer electrolytes in electrochemical applications, such as, for example, electrochemical fuel cells.
    Type: Grant
    Filed: September 21, 1993
    Date of Patent: June 6, 1995
    Assignee: Ballard Power Systems Inc.
    Inventors: Jinzhu Wei, Charles Stone, Alfred E. Steck
  • Patent number: 5354824
    Abstract: The invention relates to new fluoroelastomeric copolymers endowed with resistance to bases and suitable in particular for preparing O-rings, comprising:______________________________________ (I) VDF 47-80 mols % HFP and/or PAVE 16-30 mols % hydrogenated olefin containing 2-25 mols % 2-4 C or (II) VDF 42-80 mols % PAVE 16-30 mols % hydrogenated olefin containing 2-30 mols % 2-4 C ______________________________________The invention relates to new fluoroplastomeric copolymers endowed with resistance to bases, comprising: ______________________________________ (III) VDF 70-99 mols % HFP and/or PAVE 0-16 mols % hydrogenated olefin containing 1-30 mols % 2-4 C ______________________________________A further object of the invention is a process for preparing the abovesaid fluoroelastomeric and fluoroplastomeric copolymers.
    Type: Grant
    Filed: May 20, 1993
    Date of Patent: October 11, 1994
    Assignee: Ausimont S.p.A.
    Inventors: Vincenzo Arcella, Giulio Brinati, Margherita Albano, Anna Minutillo, Graziella Chiodini
  • Patent number: 5350821
    Abstract: Disclosed herein are novel monomers of the formula CF.sub.2 .dbd.CF(CF.sub.2).sub.n CH.sub.2 OCF.dbd.CF.sub.2, wherein n is 1, 2 or 3, and novel intermediates of the formula CF.sub.2 C1CFCl(CF.sub.2).sub.n CH.sub.2 OCF.dbd.CF.sub.2 wherein n is 1, 2 or 3. Also disclosed is a fluoro-polymer containing cyclic units when the monomer wherein n is 1 is free radically polymerized. The polymer is particularly useful in for coatings and encapsulants.
    Type: Grant
    Filed: February 16, 1994
    Date of Patent: September 27, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Andrew E. Feiring, Bruce E. Smart, Zhen-Yu Yang
  • Patent number: 5310838
    Abstract: Repeat units having pendant functional groups increase the solubility of polymers containing repeat units of perfluoro-2,2-dimethyl-1,3-dioxole.
    Type: Grant
    Filed: September 7, 1993
    Date of Patent: May 10, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Ming-Hong Hung, Paul R. Resnick
  • Patent number: 5304617
    Abstract: This invention relates to a fluorine-containing copolymer which contains a fluoroolefin unit, a vinyl ester or vinyl ether unit, and a hydroxyl group-containing vinyl ether unit in amounts of from 40 to 60 mol%, from 25 to 55 mol% and from 5 to 25 mol%, respectively, and has an intrinsic viscosity of from 0.01 to 0.05 d.lambda./g as measured in an uncured state at 30.degree. C. in tetrahydrofuran, and the ratio of a weight-average molecular weight and a number-average molecular weight measured by a gel permeation chromatography being not more than 2.0, and a process for its production. The fluorine-containing copolymer of the present invention is excellent in weatherability, retains good coatability even if used as a high solid coating, and provide a coating film excellent in clarity.
    Type: Grant
    Filed: July 22, 1991
    Date of Patent: April 19, 1994
    Assignee: Asahi Glass Company Ltd.
    Inventors: Shun-ichi Kodama, Motoi Kamba, Isao Kimura, Kazunori Chiba
  • Patent number: 5292816
    Abstract: The invention relates to new plastic materials made of heterogeneous copolymers of vinylidene fluoride and chlorotrifluoroethylene, consisting of elastomeric nodules of heterogeneous copolymers of vinylidene fluoride and chlorotrifluoroethylene which are dispersed in a crystalline continuous phase of quasi vinylidene fluoride polymer.According to another feature, the plastic materials are made of heterogeneous copolymers containing overall approximately from 10 to 22% by weight of CTFE and exhibiting a melting temperature of at least 165.degree. C. and a flexural elasticity modulus of not more than 1000 MPa. The heterogeneous copolymers are obtained by a radical copolymerisation in aqueous medium, all of the comonomers being introduced at the beginning of the copolymerisation.The plastic materials can be employed for the manufacture of flexible articles such as flexible tubular articles, sheathing for cables, coatings and films.
    Type: Grant
    Filed: January 29, 1993
    Date of Patent: March 8, 1994
    Assignee: SOLVAY (Societe Anonyme)
    Inventors: Jean-Yves Metz, Paul Plissart
  • Patent number: 5286825
    Abstract: Partially fluorinated compounds of specified formulas that are useful as chemical intermediates and monomers are disclosed. Partially fluorinated polymers prepared from one of these compounds are also disclosed. Fluoro-2,2-dimethyldioxolanes and copolymers thereof are further disclosed.
    Type: Grant
    Filed: June 14, 1993
    Date of Patent: February 15, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Douglas R. Anton, William B. Farnham, Ming-Hong Hung, Ronald J. McKinney, Paul R. Resnick
  • Patent number: 5285002
    Abstract: Fluoroalkyl sulfinates were synthesized and used as a source of fluoroalkyl radicals in aqueous emulsion polymerization. The resulting polymers contained a high level of perfluoroalkyl end groups. When fluoroalkyl disulfinates were utilized, the fluoroalkyl moiety and was incorporated in the polymer backbone. These disulfinates act as monomers, yielding fluoropolymers with specific micro structural fragments, derived from the parent perfluoro disulfinate. Novel fluoropolymers can thus be prepared.
    Type: Grant
    Filed: March 23, 1993
    Date of Patent: February 8, 1994
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Werner M. Grootaert
  • Patent number: 5284893
    Abstract: The invention provides a coating composition prepared by dissolving a fluorine-type copolymer in an organic solvent, the copolymer comprising:i) about 50 to about 90 mole % of a structural unit represented by the formula a)--CH.sub.2 --CF.sub.2 --ii) about 5 to about 30 mole % of a structural unit represented by the formula b)--CF.sub.2 --CF.sub.2 --andiii) about 5 to about 30 mole % of a structural unit represented by the formula c)--CF.sub.
    Type: Grant
    Filed: October 12, 1990
    Date of Patent: February 8, 1994
    Assignee: Daikin Industries, Ltd.
    Inventors: Motonobu Kubo, Hiroshi Inukai, Takahiro Kitahara
  • Patent number: 5283304
    Abstract: A fluorine-containing resin being soluble in an organic solvent and having excellent compatibility with a curing agent, which contains Component (A) formed of a unit having the formula ##STR1## and at least one of Component (B) formed of a unit having a cyclic hydrocarbon group introduced through a urethane bond in the molecule and Component (C) of a unit having the formula ##STR2## and which further optionally contains Component (D) of a unit formed from a vinyl monomer having a specific functional group, Component (E) of a unit formed from a vinyl monomer other than monomers forming the Components (A), (B), (C) and (D), and Component (T) of a unit formed from an acrylic resin having a specific substituent; and a coating composition containing said resin, (wherein V, Y, X, Z, R.sup.c1, R.sup.c2 and R.sup.c3 are as defined in the specification).
    Type: Grant
    Filed: April 13, 1992
    Date of Patent: February 1, 1994
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Akira Nakabayashi, Kaoru Ueyanagi, Atsushi Shimizu, Hiromasa Sasahara
  • Patent number: 5264509
    Abstract: Fluoroelastomeric copolymers exhibiting high resistance to bases and alcohols, as well as high mechanical properties and low-temperature resistance, comprising, in moles:4-75% of units of vinylidene fluoride;12-40% of units of hexafluoropropene and/or perfluorovinylether and/or hydropentafluoropropene and/or chlorotrifluoroethylene;2-35% of units of an olefin containing up to 4 carbon atoms;2-60% of units of tetrafluoroethylene, provided that, when the sum of the olefin units and the perfluorovinylether units is equal to or greater than 70%, such copolymers possess a molecular weight sufficiently high to exhibit good mechanical characteristics.
    Type: Grant
    Filed: February 8, 1993
    Date of Patent: November 23, 1993
    Assignee: Ausimont S.p.A.
    Inventors: Vincenzo Arcella, Margherita Albano, Giulio Brinati, Graziell Chiodini, Anna Minutillo
  • Patent number: 5260392
    Abstract: Fluoroelastomeric copolymers, vulcanizable by ionic methods, suitable for the manufacture of "shaft seals" and "fuel hoses", comprising by weight:______________________________________ VDF 30-47% HFP 20-40% PAVE 3-20% TFE 10-30% ______________________________________
    Type: Grant
    Filed: February 8, 1993
    Date of Patent: November 9, 1993
    Assignee: Ausimont S.p.A.
    Inventors: Vincenzo Arcella, Giulio Brinati, Margherita Albano, Anna Minutillo, Graziella Chiodini
  • Patent number: 5260393
    Abstract: Fluoroelastic copolymers, suitable for the manufacture of O-rings, comprising by weight:48-65% of VDF units21-36% of HFP units3-9% of PAVE units0-17% of TFE units
    Type: Grant
    Filed: February 8, 1993
    Date of Patent: November 9, 1993
    Assignee: Ausimont S.p.A.
    Inventors: Vincenzo Arcella, Giulio Brinati, Margherita Albano, Anna Minutillo, Graziella Chiodini
  • Patent number: 5258447
    Abstract: The invention provides a copolymer which comprises, as essential components, 25-75 mol % of a fluoroolefin such as CTFE, 10-70 mol % of a carboxylic acid vinyl ester, 3-75 mol % of a hydroxyl-containing allyl ether and 0.1-20 mol % of an unsaturated carboxylic acid having at least 6 carbon atoms in the molecule. The copolymer is soluble in various organic solvents and curable, e.g., with a blocked polyisocyanate or a modified melamine resin. The copolymer can be prepared by a suspension polymerization method in an aqueous medium and hence can be made very low in the contents of unreacted residual monomers. The copolymer is very suitable for use in electrodeposition paints.
    Type: Grant
    Filed: March 23, 1992
    Date of Patent: November 2, 1993
    Assignee: Central Glass Company, Limited
    Inventors: Toshio Koishi, Mikio Ootani, Toru Koshita
  • Patent number: 5256745
    Abstract: Group IV compounds, e.g. alkylsilane, or alkylsiloxane compounds, are used as chain transfer agent in the radical initiated polymerization of ethylenically unsaturated monomers, to give polymers comprising non-ionic end groups.
    Type: Grant
    Filed: January 15, 1993
    Date of Patent: October 26, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Werner M. Grootaert
  • Patent number: 5247036
    Abstract: The title compounds contain one or more fluorinated monomers and alkenyl isocyanurates and/or alkenyl cyanurates of the formulae ##STR1## wherein R.sup.1, R.sup.2, R.sup.4 and R.sup.5 independently of one another denote C.sub.3 -C.sub.6 -alkenyl having a terminal double bond andR.sup.3 and R.sup.6 independently of one another denote C.sub.3 -C.sub.6 -alkenyl having a terminal double bond or C.sub.1 -C.sub.5 -alkyl.The alkenyl (iso)cyanurates (I) and (II) are contained in the copolymers in an amount of 0.1-5 mol %. based on the number of moles of all the comonomers. The fluorinated monomers can also be partly replaced by comonomers which do not contain fluorine.The title compounds can be crosslinked after shaping and can then be used as elastic or dimensionally stable shaped articles.
    Type: Grant
    Filed: November 26, 1991
    Date of Patent: September 21, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ralf Kruger, Karl-Erwin Piejko, Gerhard Langstein
  • Patent number: 5231155
    Abstract: A hardenable fluorinated copolymer of fluorinated monomers and an acrylamide derivative and paints, paints and varnishes comprising such copolymers, and the process of making such hardenable copolymer.
    Type: Grant
    Filed: June 14, 1991
    Date of Patent: July 27, 1993
    Assignee: Atochem
    Inventors: Patrick Kappler, Jean-Luc Perillon
  • Patent number: 5229473
    Abstract: The present invention provides a fluorinecontaining copolymer comprising at least one fluoroolefin and at least one cyclic unsaturated compound represented by the formulas (I) and (II) ##STR1## wherein each of n and m is 0 or a positive integer and preferably 0 or an integer of from 1 to 3, l is an integer of 3 or more than 3 and preferably 3 or 4, and R.sup.1 to R.sup.10 are the same or different and each represents a hydrogen atom, a halogen atom, a hydrocarbon group or a substituted hydrocarbon group and a method of preparing the same; and a fluorine-containing copolymer comprising at least one fluoroolefin, at least one cyclic unsaturated compound selected from the compounds of the above formulas (I) and (II) and at least one of mono and diolefins and a method of preparing the same.
    Type: Grant
    Filed: August 7, 1992
    Date of Patent: July 20, 1993
    Assignee: Daikin Industries Ltd.
    Inventors: Motonobu Kobo, Hiroshi Inukai, Takahiro Kitahara, Kayoko Sugioka
  • Patent number: 5227441
    Abstract: Copolymers of fluoroethylenes and masked phenols of the formula ##STR1## wherein R.sup.1 is H, C.sub.1 -C.sub.4 -alkyl,which may be further ring substituted and in which X is OY or ##STR2## Y is Si(R.sup.3).sub.3, ##STR3## R.sup.3 is alkyl, cycloalkyl or aryl.
    Type: Grant
    Filed: September 16, 1992
    Date of Patent: July 13, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ralf Kruger, Holger Lutjens, Karl-Erwin Piejko
  • Patent number: RE35466
    Abstract: Group IV organometallic compounds, e.g. alkylsilane, or alkylsiloxane compounds, are used as chain tranfer agent in the radical initiated polymerization of ethylenically unsaturated monomers, to give polymers comprising non-ionic end groups.
    Type: Grant
    Filed: June 30, 1994
    Date of Patent: February 25, 1997
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Werner M. Grootaert