Halogen Is Fluorine Patents (Class 522/156)
  • Patent number: 7514481
    Abstract: A method of making a crosslinked polymer is provided as well as the polymer so made, the method comprising the steps of: providing a highly fluorinated fluoropolymer, typically a perfluorinated fluoropolymer, comprising pendent groups which include a group according to the formula —SO2X, where X is F, Cl, Br, OH, or —O?M+, where M+ is a monovalent cation, and exposing said fluoropolymer to electron beam radiation so as to result in the formation of crosslinks. Typically, the method according to the present invention additionally comprises the step of: forming said fluoropolymer into a membrane, typically having a thickness of 90 microns or less, more typically 60 microns or less, and most typically 30 microns or less.
    Type: Grant
    Filed: January 29, 2007
    Date of Patent: April 7, 2009
    Assignee: 3M Innovative Properties Company
    Inventors: Michael A. Yandrasits, Steven J. Hamrock, Naiyong Jing
  • Patent number: 7514480
    Abstract: Ionized irradiation can be used to improve the properties of fluoropolymers. In particular, elasticity, strain hardening, and melt strength of a fluoropolymer can be increased by LIP to an order of magnitude by exposure to controlled amounts of radiation; while polymer foams may be thermoformed and crosslinked by irradiation to provide a solvent resistance polymer foams having wide range of densities with good mechanical integrity at elevated temperature.
    Type: Grant
    Filed: June 21, 2005
    Date of Patent: April 7, 2009
    Assignee: Arkema Inc.
    Inventors: Nafih Mekhilef, Ramin Amin-Sanayei
  • Patent number: 7482393
    Abstract: A method for producing submicron polytetrafluoroethylene (“PTFE”) powder in a free-flowing, readily dispersible form. The irradiated PTFE starting material is placed in a desired solvent and undergoes grinding until the PTFE particles reach submicron size. The submicron particles are subsequently recovered from the solvent and dried to form a powder that may have particles less than 1.00 ?m in size. The dry PTFE powder may then be readily dispersed to submicron size into a desired application system. The submicron PTFE powder of this method is free-flowing, readily dispersible in various application systems, tends not to “dust” or self-agglomerate. Improved aqueous and organic dispersions of submicron PTFE particles may also be formed that display increased stability and require much less agitation than other processes of forming such dispersions. Such improved PTFE dispersions may be formed with or without the addition of surfactants, wetting agents, rheology modifiers, pH-adjusting agents, and the like.
    Type: Grant
    Filed: December 29, 2004
    Date of Patent: January 27, 2009
    Assignee: Shamrock Technologies Inc.
    Inventors: Charles A. Cody, William Neuberg, Manshi Sui, Youssef Awad
  • Patent number: 7459498
    Abstract: The present invention relates to plenum cables jacketed with a composition comprising perfluoropolymer, inorganic char-forming agent, and hydrocarbon polymer, which passes the NFPA-255 burn test.
    Type: Grant
    Filed: January 19, 2005
    Date of Patent: December 2, 2008
    Assignees: E. I. du Pont de Nemours and Company, Alpha Gary Corporation
    Inventors: Yevgeniy I. Globus, Mark A. Jozokos, John L. Netta, George Martin Pruce, Sundar Kilnagar Venkataraman
  • Patent number: 7449277
    Abstract: A polymer is obtained from (meth)acrylate having a bridged ring lactone group, (meth)acrylate having an acid-labile leaving group, and (meth)acrylate having a hydroxynaphthyl pendant. A positive resist composition comprising the polymer as a base resin, when exposed to high-energy radiation and developed, exhibits a high sensitivity, a high resolution, and a minimal line edge roughness due to controlled swell during development, and leaves minimal residues following development.
    Type: Grant
    Filed: September 20, 2006
    Date of Patent: November 11, 2008
    Assignee: Shin-Etsu Chemical C., Ltd
    Inventors: Jun Hatakeyama, Takeshi Nagata, Takanobu Takeda
  • Patent number: 7439279
    Abstract: To provide a coating composition which forms a coating film having excellent fingerprint removability and having favorable abrasion resistance and transparency, and a molded product having a coating film made of a cured product of the composition. An active energy ray curable coating composition comprising an active energy ray curable polymerizable monomer (A), a water and oil repellency-imparting agent (B) and an active energy ray polymerization initiator (C), wherein the water and oil repellency-imparting agent (B) contains a water and oil repellency-imparting agent (B-T) having a moiety (b-1) exerting water and oil repellency, an active energy ray curable functional group (b-2) and a moiety (b-3) excellent in compatibility with the polymerizable monomer (A) and a molded product having a coating film made of a cured product of the composition.
    Type: Grant
    Filed: May 13, 2005
    Date of Patent: October 21, 2008
    Assignee: Asahi Glass Company, Limited
    Inventors: Satoshi Kondo, Daisuke Shirakawa, Toshihiko Higuchi, Hirotsugu Yamamoto
  • Publication number: 20080143003
    Abstract: The present invention provides inks and methods for making colored silicone hydrogel contact lenses. The ink of the invention comprises an actinically-curable binder copolymer comprising fluorine-containing segments and is characterized by having capability to be cured actinically or thermally to form a colored film on a molding surface of a mold or a silicone hydrogel contact lens and by having an increased durability in a solvated state in a silicone-hydrogel lens formulation in relation to a control colored film obtained from a control ink including an actinically-curable fluorine-free binder copolymer. The invention also provides methods for making colored silicone hydrogel contact lenses based on print-on-mold processes for producing colored contact lenses.
    Type: Application
    Filed: December 12, 2007
    Publication date: June 19, 2008
    Inventor: John Christopher Phelan
  • Patent number: 7348366
    Abstract: An elastomer blend is made by admixing fluoroelastomer and fluorinated silicone polymer (with optional filler and/or conductive particulate) into a polymeric admixture in weight ratios to provide a low vaporous hydrocarbon permeation rate and high thermal strain value in thermally robust elastomer cured from the blend. The blend is of especial use for making gaskets for use in high stress conditions at elevated operating temperatures.
    Type: Grant
    Filed: April 7, 2005
    Date of Patent: March 25, 2008
    Assignee: Freudenberg-NOK General Partnership
    Inventors: Francis Joseph Walker, Paul J. Hochgesang
  • Patent number: 7294673
    Abstract: A method of modifying a polymeric material whereby the polymeric material is modified to give a highly durable surface without decreasing its strength. Namely, a polymeric material is modified by the method comprising a combination of an impregnation step, an activation step, a step of grafting a monomer and a step of a treatment with a hydrophilic polymer. Thus, the hydrophilic nature, adhesiveness, and so forth of polymeric materials such as polyolefins can be improved without causing any decrease in the practical strength. The thus obtained polymeric materials are usable in articles with a need for high water absorptivity and high adhesiveness, for example, water-absorbing materials and water-retaining materials for medical, sanitary, cosmetic articles or supplies, agricultural materials, synthetic papers, filters and fiber products for clothes, for improving adhesiveness of composite materials and the like.
    Type: Grant
    Filed: June 28, 2002
    Date of Patent: November 13, 2007
    Assignee: FiberMark Gessner GmbH & Co.
    Inventor: Hitoshi Kanazawa
  • Patent number: 7282525
    Abstract: A pellicle comprises a pellicle film and a pellicle frame for supporting the pellicle film, wherein the pellicle film is adhered to the pellicle frame through an adhesive layer comprising a fluorine-containing polymer and a substance resulting from curing of an ultraviolet-curing fluorine-containing monomer. A producing method of a pellicle including a pellicle film and a pellicle frame for supporting the pellicle film, comprises a step of adhering the pellicle film to the pellicle frame through an adhesive comprising a fluorine-containing polymer and an ultraviolet-curing fluorine-containing monomer.
    Type: Grant
    Filed: December 27, 2001
    Date of Patent: October 16, 2007
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Hiroyuki Kurata, Hideto Matsuoka
  • Patent number: 7265162
    Abstract: A method is provided for making a crosslinked polymer electrolyte, typically in the form of a membrane for use as a polymer electrolyte membrane in an electrolytic cell such as a fuel cell, as well as the polymer so made, the method comprising application of electron beam radiation to a highly fluorinated fluoropolymer comprising: a backbone derived in part from tetrafluoro-ethylene monomer, first pendent groups which include a group according to the formula —SO2X, where X is F, Cl, Br, OH or —O?M+, where M+ is a monovalent cation, and second pendent groups which include Br, Cl or I. Typically, the membrane has a thickness of 90 microns or less, more typically 60 or less, and most typically 30 microns or less.
    Type: Grant
    Filed: November 13, 2003
    Date of Patent: September 4, 2007
    Assignee: 3M Innovative Properties Company
    Inventors: Michael A. Yandrasits, Steven J. Hamrock, Klaus Hintzer, Arne Thaler, Tatsuo Fukushi, Naiyong Jing, Kai Helmut Lochhaas
  • Patent number: 7241817
    Abstract: The present invention relates to a process for grafting an unsaturated monomer onto a fluoropolymer, having the steps of: a) melt blending the fluoropolymer with the unsaturated monomer; b) forming the blend obtained in a) into films, sheets, granules or powder; c) exposing the products from step b), in the absence of air, to photon (?) or electron (?) irradiation with a dose of between 1 and 15 Mrad; and d) optionally treating the product obtained at c) in order to remove all or part of the unsaturated monomer that has not been grafted onto the fluoropolymer. Structures made with these materials are barriers to many fluids and in particular to petrol and to air-conditioning fluids and may be formed into bottles, tanks, containers, pipes, hoses and vessels of all sorts. They may also be converted into films with which packaging is made.
    Type: Grant
    Filed: June 2, 2004
    Date of Patent: July 10, 2007
    Assignee: Arkema France
    Inventors: Anthony Bonnet, Barbara Ramfel, Fabrice Chopinez, Karine Triballier, Michael Werth, Thierry Pascal
  • Patent number: 7220788
    Abstract: The present invention relates to a fluororubber molded article obtained by subjecting a fluororubber composition to crosslinking by irradiation of ionizing radiation, wherein the fluororubber composition comprises: (i) a raw rubber having a metal element content of 1.5% or less and comprising a tetrafluoroethylene-propylene copolymer; and (ii) a prepolymer of triallyl isocyanurate. Also disclosed is a method for producing the fluororubber molded article.
    Type: Grant
    Filed: February 27, 2004
    Date of Patent: May 22, 2007
    Assignee: Nichias Corporation
    Inventors: Naoya Kuzawa, Mitsuyuki Nakano, Hitoshi Ogura, Masayuki Saito
  • Patent number: 7220799
    Abstract: Unsintered poly(tetrafluoroethylene) resin feeds are treated with ionizing radiation in an absorbed dose of no more than 1,000 Gy at room temperature in air so that only the melting temperature of the resin feeds is shifted toward the lower end without changing the quantities of heat of fusion and crystallization.
    Type: Grant
    Filed: May 28, 2004
    Date of Patent: May 22, 2007
    Assignee: Japan Atomic Energy Research Institute
    Inventors: Akira Udagawa, Akihiro Oshima
  • Patent number: 7179847
    Abstract: A method of making a crosslinked polymer is provided as well as the polymer so made, the method comprising the steps of: providing a highly fluorinated fluoropolymer, typically a perfluorinated fluoropolymer, comprising pendent groups which include a group according to the formula —SO2X, where X is F, Cl, Br, OH, or —O?M+, where M+ is a monovalent cation, and exposing said fluoropolymer to electron beam radiation so as to result in the formation of crosslinks. Typically, the method according to the present invention additionally comprises the step of: forming said fluoropolymer into a membrane, typically having a thickness of 90 microns or less, more typically 60 microns or less, and most typically 30 microns or less.
    Type: Grant
    Filed: November 13, 2003
    Date of Patent: February 20, 2007
    Assignee: 3M Innovative Properties Company
    Inventors: Michael A. Yandrasits, Steven J. Hamrock, Naiyong Jing
  • Patent number: 7112614
    Abstract: A method is provided for obtaining crosslinked polymers, particularly fluorinated polymers having pendent sulfonic acid groups, by crosslinking through pendent groups which include a sulfonyl chloride group (—SO2Cl). The sulfonyl chloride group may be removed by application of electromagnetic radiation, typically in the ultraviolet band, or a radical initiator, leaving behind a radical which readily binds covalently to other polymer strands or to crosslinking agents to form crosslinks. Typically, the polymer is made by providing a polymer comprising pendent groups which include a group according to the formula —SO2F and converting at least a portion of the —SO2F groups to —SO2Cl. After crosslinking, the remaining —SO2F groups may be converted to sulfonic acid groups, yielding a crosslinked polymer electrolyte. Such crosslinked polymer electrolytes may be used to make polymer electrolyte membranes (PEM's) that may be used in electrolytic cells such as fuel cells.
    Type: Grant
    Filed: December 8, 2003
    Date of Patent: September 26, 2006
    Assignee: 3M Innovative Properties Company
    Inventors: Naiyong Jing, Steven J. Hamrock
  • Patent number: 7112640
    Abstract: A fluorocopolymer which comprises repeating units (a) based on tetrafluoroethylene and/or chlorotrifluoroethylene, repeating units (b) based on a cyclic hydrocarbon monomer having a dicarboxylic anhydride group and an endocyclic polymerizable unsaturated group, and repeating units (c) based on other monomer, wherein the repeating units (a) are from 50 to 99.89 mol %, the repeating units (b) are from 0.01 to 5 mol % and the repeating units (c) are from 0.1 to 49.99 mol %, based on the total molar amount of the repeating units (a), (b) and (c), and which has a volume flow rate of from 0.1 to 1,000 mm3/sec., and a laminate and coated product thereof. The fluorocopolymer is excellent in adhesion, heat resistance, weather resistance, stress cracking resistance and fuel barrier properties. The laminate is excellent in interlaminar bonding and fuel barrier properties.
    Type: Grant
    Filed: September 14, 2005
    Date of Patent: September 26, 2006
    Assignee: Asahi Glass Company, Limited
    Inventors: Atsushi Funaki, Hiroki Kamiya, Shigeru Aida, Toshiyuki Chisaka
  • Patent number: 7074841
    Abstract: A method is provided for making a crosslinked polymer electrolyte, typically in the form of a membrane for use as a polymer electrolyte membrane in an electrolytic cell such as a fuel cell, by trimerization of nitrile groups contained on groups pendant from the polymer. The resulting polymer electrolyte membrane comprises a highly fluorinated polymer comprising: a perfluorinated backbone, first pendent groups which comprise sulfonic acid groups, and crosslinks comprising trivalent groups according to the formula: The first pendent groups are typically according to the formula: —R1—SO3H, where R1 is a branched or unbranched perfluoroalkyl or perfluoroether group comprising 1–15 carbon atoms and 0–4 oxygen atoms, most typically —O—CF2—CF2—CF2—CF2—SO3H or —O—CF2—CF(CF3)—O—CF2—CF2—SO3H.
    Type: Grant
    Filed: November 13, 2003
    Date of Patent: July 11, 2006
    Inventors: Michael A. Yandrasits, Steven J. Hamrock, Werner M. Grootaert, Miguel A. Guerra, Naiyong Jing
  • Patent number: 7060738
    Abstract: A method is provided for making a crosslinked polymer electrolyte, typically in the form of a membrane for use as a polymer electrolyte membrane in an electrolytic cell such as a fuel cell, as well as the polymer so made, the method comprising application of ultraviolet radiation to a highly fluorinated fluoropolymer comprising: a backbone derived in part from tetrafluoro-ethylene monomer, first pendent groups which include a group according to the formula —SO2X, where X is F, Cl, Br, OH or —O?M+, where M+ is a monovalent cation, and second pendent groups which include Br, Cl or I. Typically, the membrane has a thickness of 90 microns or less, more typically 60 or less, and most typically 30 microns or less.
    Type: Grant
    Filed: December 11, 2003
    Date of Patent: June 13, 2006
    Assignee: 3M Innovative Properties Company
    Inventors: Naiyong Jing, Steven J. Hamrock, Michael A. Yandrasits
  • Patent number: 7014980
    Abstract: A photoresist composition is provided that includes a polymer having at least one acrylate or methacrylate monomer having a formula where R1 represents hydrogen (H), a linear or branched alkyl group of 1 to 20 carbons, or a semi- or perfluorinated linear or branched alkyl group of 1 to 20 carbons; and where R2 represents an unsubstituted aliphatic group or a substituted aliphatic group having zero or one trifluoromethyl (CF3) group attached to each carbon of the substituted aliphatic group, or a substituted or unsubstituted aromatic group; and where R3 represents hydrogen (H), methyl (CH3), trifluoromethyl (CF3), difluoromethyl(CHF2), fluoromethyl (CH2F), or a semi- or perfluorinated aliphatic chain; and where R4 represents trifluoromethyl (CF3), difluoromethyl (CHF2), fluoromethyl (CH2F), or a semi- or perfluorinated substituted or unsubstituted aliphatic group. A method of patterning a substrate using the photoresist composition is also provided herein.
    Type: Grant
    Filed: August 12, 2004
    Date of Patent: March 21, 2006
    Assignee: International Business Machines Corporation
    Inventors: Robert David Allen, Gregory Breyta, Phillip Brock, Richard A. DiPietro, Debra Fenzel-Alexander, Carl Larson, David R. Medeiros, Dirk Pfeiffer, Ratnam Sooriyakumaran, Hoa D. Truong, Gregory M. Wallraff
  • Patent number: 6884827
    Abstract: A seal ring seals operating oil hermetically and is attached to an annular seal ring groove provided on an outer circumference of a shaft member. The seal ring comprises fluororesin, metal powder having a hardness equal to or more than that of any of a side surface of the seal ring groove serving as a sliding partner and an inner circumferential surface of a housing engaged relatively rotatable with the outer circumference of the shaft member, and modified fluororesin formed by irradiating an ionizing radiation in a range from 1 kGy to 10 MGy inclusive in a state of being heated up to a melting point thereof or higher under an inert gas atmosphere with an oxygen partial pressure of 1.33 kPa or less.
    Type: Grant
    Filed: April 1, 2003
    Date of Patent: April 26, 2005
    Assignees: Nissan Motor Co., Ltd., Hitachi Cable Ltd.
    Inventors: Tomohito Ota, Tomihito Hashimoto, Yasuaki Yamamoto, Hiroo Kusano
  • Patent number: 6833393
    Abstract: A curable composition comprising a compound (A) having at least one active energy ray curable polymerizable functional group, a fluorine-containing copolymer (B) obtained by (1) copolymerizing a polymerizable monomer (a) having a polyfluoroalkyl group and a polymerizable monomer (b) having a photo-curable functional group, or (2) introducing a photo-curable functional group into a fluorine-containing copolymer (D) obtained by copolymerizing a polymerizable monomer (a) having a polyfluoroalkyl group and a polymerizable monomer (d) having a group capable of introducing a photo-curable functional group, and a photopolymerization initiator.
    Type: Grant
    Filed: December 4, 2001
    Date of Patent: December 21, 2004
    Assignee: Asahi Glass Company, Limited
    Inventors: Kenji Ishizeki, Hirotsugu Yamamoto, Yuichi Yamamoto
  • Patent number: 6806026
    Abstract: A photoresist composition is provided that includes a polymer having at least one acrylate or methacrylate monomer having a formula: where R1 represents hydrogen (H), a linear or branched alkyl group of 1 to 20 carbons, or a semi- or perfluorinated linear or branched alkyl group of 1 to 20 carbons; and where R2 represents an unsubstituted aliphatic group or a substituted aliphatic group having zero or one trifluoromethyl (CF3) group attached to each carbon of the substituted aliphatic group, or a substituted or unsubstituted aromatic group; and where R3 represents hydrogen (H), methyl (CH3), trifluoromethyl (CF3), difluoromethyl (CHF2), fluoromethyl (CH2F), or a semi- or perfluorinated aliphatic chain; and where R4 represents trifluoromethyl (CF3), difluoromethyl (CHF2), fluoromethyl (CH2F), or a semi- or perfluorinated substituted or unsubstituted aliphatic group. A method of patterning a substrate using the photoresist composition is also provided herein.
    Type: Grant
    Filed: May 31, 2002
    Date of Patent: October 19, 2004
    Assignee: International Business Machines Corporation
    Inventors: Robert David Allen, Gregory Breyta, Phillip Brock, Richard A. DiPietro, Debra Fenzel-Alexander, Carl Larson, David R. Medeiros, Dirk Pfeiffer, Ratnam Sooriyakumaran, Hoa D. Truong, Gregory M. Wallraff
  • Patent number: 6774155
    Abstract: The invention is directed to methods for fabricating devices from polymer precursors, along with devices so fabricated. The methods of the invention include the steps of plasma treating a polymer based resin, paste, preform billet, or extrudate, and employing the treated polymer in the fabricated device. According to one embodiment, the fabricated device can include implantable prosthetics such as heart valves, sutures, vascular access devices, vascular grafts, shunts, catheters, single layered membranes, double layered membranes, and the like. Devices fabricated according to one embodiment of the invention include regions having selected porosity, permeability and/or chemistry characteristics.
    Type: Grant
    Filed: July 16, 2002
    Date of Patent: August 10, 2004
    Assignee: Atrium Medical Corporation
    Inventors: Paul Martakos, Thomas M. Swanick, Theodore Karwoski
  • Patent number: 6762215
    Abstract: Unsintered poly(tetrafluoroethylene) resin feeds are treated with ionizing radiation in an absorbed dose of no more than 1,000 Gy at room temperature in air so that only the melting temperature of the resin feeds is shifted toward the lower end without changing the quantities of heat of fusion and crystallization.
    Type: Grant
    Filed: February 25, 2002
    Date of Patent: July 13, 2004
    Assignee: Japan Atomic Energy Research
    Inventors: Akira Udagawa, Akihiro Oshima
  • Patent number: 6627673
    Abstract: The present invention relates to shape deformable materials, which are capable of (1) being deformed, (2) storing an amount of shape deformation, and (3) recovering at least a portion of the shape deformation when exposed to a humid environment. The shape deformable materials can advantageously be in the form of films, fibers, filaments, strands, nonwovens, and pre-molded elements. The shape deformable materials of the present invention may be used to form products, which are both disposable and reusable. More specifically, the shape deformable materials of the present invention may be used to produce products such as disposable diapers, training pants, incontinence products, and feminine care products.
    Type: Grant
    Filed: July 24, 2001
    Date of Patent: September 30, 2003
    Assignee: Kimberly-Clark Worldwide, Inc.
    Inventors: Vasily A. Topolkaraev, Dave A. Soerens
  • Patent number: 6610761
    Abstract: The present invention provides an ionizing radiation irradiated rubber molded product and a process for preparing the same, the rubber molded product being prepared by irradiating with an ionizing radiation a preform comprising 5 to 95% by weight of a fluororubber containing vinylidene fluoride copolymerized therein in a proportion of 45 to 88 mole % and having a number average molecular weight of 5,000 to 200,000, and 95 to 5% by weight of an acrylic rubber.
    Type: Grant
    Filed: December 8, 2000
    Date of Patent: August 26, 2003
    Assignee: Daikin Industries, Ltd.
    Inventors: Kazuhisa Matsumoto, Yoshihiro Shirai
  • Patent number: 6593392
    Abstract: The invention provides an organic/inorganic hybrid material with low optical loss at telecommunications wavelengths. Energy curable compositions of the present invention include condensed silica nanoparticles, a fluorinated silane coupling agent, an energy curable silane coupling agent, and a halogenated monomer or oligomer. Polymeric materials of the present invention include condensed silica nanoparticles having a mixture of organosilane coupling agents covalently bound to the exterior surface of the nanoparticles and a halogenated solid polymer matrix, wherein the mixture of organosilane coupling agents includes an at least partially fluorinated coupling agent, and a coupling agent covalently bound to the polymer matrix. The materials of the present invention are useful in making low-loss optical devices for telecommunications applications.
    Type: Grant
    Filed: June 22, 2001
    Date of Patent: July 15, 2003
    Assignee: Corning Incorporated
    Inventor: Zhikai Wang
  • Patent number: 6573311
    Abstract: The invention is directed to methods for fabricating devices from polymer precursors, along with devices so fabricated. The methods of the invention include the steps of plasma treating a polymer based resin, paste, preform billet, or extrudate, and employing the treated polymer in the fabricated device. According to one embodiment, the fabricated device can include implantable prosthetics such as heart valves, sutures, vascular access devices, vascular grafts, shunts, catheters, single layered membranes, double layered membranes, and the like. Devices fabricated according to one embodiment of the invention include regions having selected porosity, permeability and/or chemistry characteristics.
    Type: Grant
    Filed: September 22, 1999
    Date of Patent: June 3, 2003
    Assignee: Atrium Medical Corporation
    Inventors: Paul Martakos, Thomas M. Swanick, Theodore Karwoski
  • Patent number: 6552099
    Abstract: A fluororesin heated at a temperature at or above the melting point of the resin is exposed in an inert gas atmosphere having an oxygen concentration of not more than 10 Torr to an ionizing radiation at a radiation dose of 0.1 kGy to 10 MGy to prepare a crosslinked fluororesin. The crosslinked fluororesin is exposed to an ionizing radiation at a radiation dose of 10 kGy to 5 MGy, and is then brought into contact with a functional group-containing organic compound to cause a graft reaction. By virtue of this constitution, a modified fluororesin is provided which has satisfactory mechanical strength and, at the same time, has, imparted thereto, for example, ion-exchange capacity, hydrophilicity, adhesive property, or abrasion resistance.
    Type: Grant
    Filed: June 8, 2001
    Date of Patent: April 22, 2003
    Assignee: Hitachi Cable, Ltd
    Inventors: Yasuaki Yamamoto, Hiroo Kusano, Hideki Yagyu, Hajime Nishi
  • Patent number: 6541537
    Abstract: A compound and a method of forming a photopolymerizable acrylated glycidyl acrylic terpolymer resin compound is disclosed. The polymeric resin may be formed in a two-step process. A photopolymerizable acrylic hybrid polymer is suitable for forming films having glass transition temperatures from about −55 degrees C. to about 110 degrees C. A non-aromatic photopolymerizable acrylate polymer may be formed by combining, in a first step, a reactive source of epoxide ion groups. In a second step, the glycidyl acrylic terpolymer formed in the first step is reacted with a catalyst and a source of unsaturated acid or anhydride to form an acrylate polymer. A ring opening reaction is employed such that an acid or an anhydride containing a conjugated double bond forms an acrylated acrylic, an acrylated fluorinated acrylic, an acrylated silonted acrylic, or an acrylated halogenated grafted acrylic. The cure process is initiated with specific UV or visible light promotors and/or with a UV or visible light source.
    Type: Grant
    Filed: January 19, 2001
    Date of Patent: April 1, 2003
    Assignee: Renaissance Technology LLC
    Inventor: Daniel W. Catena
  • Patent number: 6517910
    Abstract: In one aspect the invention provides an energy efficient polymerization method comprising irradiating a polymerizable composition and a photoinitiator with a source of essentially monochromatic radiation where the photoinitiator and the wavelength of the radiation source are selected such that the extinction coefficient of the photoinitiator at the peak wavelength of the source is greater than about 1000 M−1 cm−1 and such that the photoinitiator absorbs at least two percent of the actinic radiation incident on the coating. In another aspect the invention provides energy efficient methods of polymerizing polymerizable compositions and crosslinking crosslinkable compositions by irradiating the respective compositions with a low power source of essentially monochromatic radiation. The low power energy sources have an input power of less than about 10 W/cm.
    Type: Grant
    Filed: February 6, 2001
    Date of Patent: February 11, 2003
    Assignee: 3M Innovative Properties Company
    Inventors: Robin E. Wright, George F. Vesley
  • Publication number: 20020161067
    Abstract: Unsintered poly(tetrafluoroethylene) resin feeds are treated with ionizing radiation in an absorbed dose of no more than 1,000 Gy at room temperature in air so that only the melting temperature of the resin feeds is shifted toward the lower end without changing the quantities of heat of fusion and crystallization.
    Type: Application
    Filed: February 25, 2002
    Publication date: October 31, 2002
    Applicant: Japan Atomic Energy Research Institute
    Inventors: Akira Udagawa, Akihiro Oshima
  • Publication number: 20020155228
    Abstract: This invention aims to make it possible to obtain curing surfaces with different surface free energies, and to provide a method of curing an ionizing radiation curing resin composition which can be used as a coating material. Further, it aims to provide a surface modification method which permits surfaces of different surface free energy to be obtained. The above object is achieved by a method of curing a mixture comprising an ionizing radiation curing resin, characterized in that at least part of a mixture comprising 0.01-10 weight parts of a compound (b) having a surface free energy not exceeding 25 mN/m relative to 100 weight parts of an ionizing radiation curing resin composition (a) having a surface free energy of at least 30 mN/m, is cured by irradiating it with ionizing radiation in contact with a medium having a surface free energy higher than that of the ionizing radiation curing resin composition (a).
    Type: Application
    Filed: February 19, 2002
    Publication date: October 24, 2002
    Applicant: KURARAY CO., LTD.
    Inventors: Atsushi Nagasawa, Takahiro Kitano, Keiji Kubo, Katsuya Fujisawa
  • Patent number: 6465575
    Abstract: A fluoroplastic-based product having reduced friction and improved abrasion resistance having excellent abrasion resistance as well as good characteristics being inherent to fluoroplastics comprises a fluoroplastic molded material containing a modified fluoroplastic prepared by applying ionizing radiation to a fluoroplastic (I) heated at the melting point or a higher temperature under an inert gas atmosphere having 10 torr or less oxygen concentration within a range of irradiation doses of from 1 KGy to 10 MGy; and an unmodified fluoroplastic (II).
    Type: Grant
    Filed: October 20, 1999
    Date of Patent: October 15, 2002
    Assignee: Hitachi Cable, Ltd.
    Inventors: Hiroo Kusano, Yasuaki Yamamoto, Hideki Yagyu
  • Patent number: 6451386
    Abstract: A process using acrylate monomers and ultraviolet light permits modification of porous polymeric materials without the use of a free radical initiator is described as is the material so modified. The modified polymeric material exhibits new properties such as wetability and advantageous flow characteristics that are useful in filtration.
    Type: Grant
    Filed: August 30, 2000
    Date of Patent: September 17, 2002
    Assignee: PTI Advanced Filtration, Inc.
    Inventor: John A. Simonetti
  • Patent number: 6423760
    Abstract: The present invention provides a fully vulcanized powdery rubber having a particle size of from 20 to 2000 nm, its preparation and use. The vulcanized powdery rubber is obtained by irradiating a rubber latex having a particle size of from 20 to 2000 nm with a high-energy irradiation. The vulcanized powdery rubber is very easily to be dispersed into various plastics, and thus can be mixed with various plastics to prepare toughened plastics and fully valcanized thermoplastic elastomers.
    Type: Grant
    Filed: October 30, 2000
    Date of Patent: July 23, 2002
    Assignees: China Petro-Chemical Corporation, Beijing Research Institute of Chemical Industry, Sinopec
    Inventors: Jinliang Qiao, Genshuan Wei, Xiaohong Zhang, Shijun Zhang, Jianming Gao, Wei Zhang, Yiqun Liu, Jiuqiang Li, Fengru Zhang, Renli Zhai, Jingbo Shao, Kunkai Yan, Hua Yin
  • Patent number: 6423412
    Abstract: The invention is embodied in an electrical device which includes at least a layer of a ferroelectric polyvinylidine fluoride polymer that has been processed to exhibit an electrostrictive strain of 4% or more when an electric field gradient of 50 megavolts per meter or greater is applied thereacross. The processing of the polymer preferably involves subjecting it to either electron beam radiation or gamma radiation. The polyvinylidine flouride polymer is selected from the group of: polyvinylidine fluoride, polyvinylidine fluoride-trifluoroethylene P(VDF-TrFE), polyvinylidine fluoride tetrafluoroethylene P(VDF-TFE), polyvinylidine fluoride trifluoroethylene-hexafluoropropylene P(VDF-TFE-HFE) and polyvinylidine fluoride-hexafluoropropylene P(VDF-HFE).
    Type: Grant
    Filed: November 18, 1998
    Date of Patent: July 23, 2002
    Assignee: The Penn State Research Foundation
    Inventors: Qiming Zhang, Vivek Bharti
  • Patent number: 6403673
    Abstract: A water dispersed primer composition comprising a solution of a halogenated hydrocarbon polymer in organic solvent; and a dispersing agent added to the solution to form a fluid primer to be dispersed in water to provide the water dispersed primer composition. Optionally, fluid primers may include photoreactive components to provide photoreactive water dispersed primer compositions. The invention further includes water based priming adhesive compositions comprising an adhesive dispersion of an adhesive polymer dispersed in water, and a primer mixed with the adhesive dispersion to form the priming adhesive.
    Type: Grant
    Filed: January 18, 2001
    Date of Patent: June 11, 2002
    Assignee: 3M Innovative Properties Company
    Inventor: James D. Groves
  • Patent number: 6348516
    Abstract: Process for using microwave irradiation to prepare solutions of polymers functionalized with acid groups The invention relates to a process for preparing aqueous, hydrous and anhydrous solutions of polymers functionalized with acid groups, which comprises using microwave radiation to supply the heat required to prepare the solution. The solutions are suitable as a starting material for producing gas diffusion electrodes, fuel cells and polymer-electrolyte-stabilized platinum nanoparticles.
    Type: Grant
    Filed: July 6, 2000
    Date of Patent: February 19, 2002
    Assignee: Celanese Ventures GmbH
    Inventors: Thomas Soczka-Guth, Helmut Witteler, Gregor Deckers, Georg Frank, Kilian Brehl, Jürgen Lenze, Harald Bönsel, Rüdiger Knauf
  • Patent number: 6340718
    Abstract: A source of radiation (10,12), particularly a pulsed accelerated electron beam, directs a beam of radiation through an irradiation chamber (14, 50). The irradiation chamber is depleted of oxygen and oxygen containing gases, such as being drawn to a vacuum of 10−1 or greater Torr by a vacuum pump (20, 52). Particulate fluoropolymer material is entrained (36) in substantially oxygen free gas and conveyed through the irradiation chamber. The accelerated electrons break chemical bonds in the fluoropolymer particles and electrostatically charge the particles. Magnetic fields (42, 60) of different polarity rotate the charged particles such that they are irradiated from different sides. The irradiated fluoropolymer particles are cooled (24) and separated (26) from the entraining gas. The entraining gas is recirculated through pneumatic line (34) for a continuous cycle. In an alternate batch processing embodiment, the fluoropolymer material is placed in the shallow container (50) which is sealed and evacuated.
    Type: Grant
    Filed: July 24, 2000
    Date of Patent: January 22, 2002
    Assignee: Steris INC
    Inventors: Sergey Alexandrovich Korenev, John Masefield, Jerry Kriebel
  • Patent number: 6316518
    Abstract: The invention includes a method of increasing polymerization within a condensation polymer. A substantially dry condensation polymer material is provided. The material is exposed to radiation having a frequency less than microwave frequency for a time of at least about 0.5 hour to increase an amount of polymerization within the material. The invention also includes a method of treating a polyamide material. A polymeric polyamide material is provided and exposed to first radiation having a first power intensity. The material is then exposed to second radiation having a second power intensity. The first power intensity is higher than the second power intensity. Additionally, the invention includes an apparatus. The apparatus includes an inlet port through which a feed material enters the apparatus, and an outlet port through which the feed material passes out of the apparatus.
    Type: Grant
    Filed: February 3, 2000
    Date of Patent: November 13, 2001
    Assignee: Advanced Polymer Technology, Inc.
    Inventors: L. Myles Phipps, Eric J. Swenson
  • Patent number: 6184339
    Abstract: Disclosed are fluorinated materials for use in dental uses and non-dental uses, e.g., adhesives or coatings. Multifunctional monomers and prepolymers with pendant (meth)acrylate groups were prepared from epoxide ring-opening reactions. Resins based on the fluorinated monomers and prepolymers with diluent comonomers, were photocured as composites with particulate fillers. Fluorine contents of the prepolymers ranged from 15 to 65%. Composites with high transverse strength (up to 120 MPa), low water sorption (as low as 0.11 mass %) and extremely low polymerization shrinkage (as low as 3.4% by volume) were obtained. The fluorinated resins may be employed to produce hydrophobic dental composite materials with high strength and low polymerization shrinkage.
    Type: Grant
    Filed: November 12, 1997
    Date of Patent: February 6, 2001
    Assignee: The United States of America as represented by the Secretary of the Commerce
    Inventors: Jeffrey W. Stansbury, Joseph M. Antonucci, Kyung M. Choi
  • Patent number: 6180687
    Abstract: In vivo polymerizable intraocular lens compositions which comprise substituted fluoroalkyl or perfluoroalkyl monomers having anionic, cationic, and/or nonionic surface active functionality in the unsaturated fluorophobic ends. The compositions are preferably cured by UV photoinitiation and are useful in repairing torn or detached retinal tissue or forming intraocular lenses in situ.
    Type: Grant
    Filed: May 17, 1999
    Date of Patent: January 30, 2001
    Assignees: Alcon Laboratories, Inc., University of Southern Mississippi
    Inventors: Mark E. Hammer, Steven T. Charles, John C. Lang, Robert Y. Lochhead, Lon J. Mathias
  • Patent number: 6160031
    Abstract: A process for decomposing a polymer which is capable of undergoing thermal depolymerization to its monomer or monomers, such as for example poly(methylmethacrylate), and for the recovery of at least one of the monomers, includes the steps of subjecting the polymer in solid, gel, partially molten or molten form to microwave heating for a time and at a temperature sufficient to decompose the polymer to produce the monomer or monomers in gaseous, liquid or solid form, without substantial decomposition of the monomer or monomers, and recovering at least one of the monomer or monomers. The monomer or monomers may then be reused for plymerisation.
    Type: Grant
    Filed: May 19, 1999
    Date of Patent: December 12, 2000
    Assignee: AECI Limited
    Inventors: Ian Douglas Poree, Karol Paula Cameron, Janine Alison Bloem, Fritz Dieter Schlosser, Alison McGowan
  • Patent number: 6063828
    Abstract: A curable underfill encapsulant composition, suitable for use in semiconductor packaging, comprises one or more mono- or polyfunctional maleimide compounds, or one or more mono- or polyfunctional vinyl compounds other than maleimide compounds, or a combination of maleimide and vinyl compounds, with a free radical curing agent, and optionally, one or more fillers.
    Type: Grant
    Filed: July 2, 1998
    Date of Patent: May 16, 2000
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventors: Bodan Ma, Quinn K. Tong
  • Patent number: 6043294
    Abstract: Chemical reaction is effected utilizing light of an appropriate frequency supplied preferably via optical fibers to one or more light extractors having light-emissive surfaces in contact with reactants. The light can be concentrated before being delivered. Wave guides and a plurality of such extractors can be provided within the vessel.
    Type: Grant
    Filed: January 29, 1998
    Date of Patent: March 28, 2000
    Assignee: Gate Technologies International, Inc.
    Inventor: Aharon Zeev Hed
  • Patent number: 5994426
    Abstract: A solid-polymer-electrolyte membrane for a polymer-electrolyte fuel cell is formed of a synthetic resin. The synthetic resin includes a main chain, and a hydrocarbon-based side chain. The main chain is formed as a film, and formed of a copolymer made from a fluorocarbon-based vinyl monomer and a hydrocarbon-based vinyl monomer. The hydrocarbon-based side chain involves a sulfonic group. The solid-polymer-electrolyte membrane exhibits a high strength and flexibility, but a low electric resistance, and can be produced at a reduced manufacturing cost. Thus, the solid-polymer-electrolyte membrane can be effectively applied to construct polymer-electrolyte fuel cells.
    Type: Grant
    Filed: January 23, 1998
    Date of Patent: November 30, 1999
    Assignee: Aisin Seiki Kabushiki Kaisha
    Inventors: Shinji Nezu, Masaki Gondo
  • Patent number: 5985949
    Abstract: A product having reduced friction and improved abrasion resistance comprises a formed resin containing at least one fluorine-containing polymer which is exposed to an ionizing radiation. The formed resin may include from 1 to 100 weight percent of the fluorine-containing polymer in the form of powder, and from 99 to 0 percent of a high molecule polymer which is not exposed to the ionizing radiation. The fluorine-containing polymer is preferably exposed to the ionizing radiation for a total dose of from 1 KGy to 10 MGy in the absence of oxygen at a temperature not lower than the melting point of a starting fluorine-containing polymer.
    Type: Grant
    Filed: April 10, 1997
    Date of Patent: November 16, 1999
    Assignees: Japan Atomic Energy Research Institute, Hitachi Cable, Ltd., Raytech Corporation, Asahi Glass Co., Ltd.
    Inventors: Tadao Seguchi, Noboru Kasai, Akinari Nakayama, Hideki Yagyu, Yoneho Tabata, Kazushige Otsuhata, Shigetoshi Ikeda, Akihiro Ohshima, Mitsuharu Morozumi, Masumi Nomura
  • Patent number: 5986012
    Abstract: This invention concerns a process for fluorinating a perfluoroelastomer which has previously been crosslinked by exposure to ionizing radiation. The resulting product has reduced outgassing. This makes perfluoroelastomer parts that have undergone the process particularly useful in clean rooms and for semiconductor manufacturing.
    Type: Grant
    Filed: February 12, 1993
    Date of Patent: November 16, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: John Michael Legare, Anestis Leonidas Logothetis