At Least One Reactant Contains Halogen Patents (Class 522/187)
-
Patent number: 8893725Abstract: The invention provides a polymer prepared from a substituted 1,3-butadiene (such as neophytadiene) derived from a plant of the Nicotiana species. The invention also provides smoking articles and smokeless tobacco compositions that include the polymers described herein. Further, the invention provides a method of polymerizing a substituted 1,3-butadiene derived from a plant of the Nicotiana species, the method including reacting a substituted 1,3-butadiene derived from a plant of the Nicotiana species with one or more reagents selected from the group consisting of an anionic initiator, a radical initiator, and a Ziegler-Natta catalyst.Type: GrantFiled: January 28, 2011Date of Patent: November 25, 2014Assignee: R. J. Reynolds Tobacco CompanyInventors: Michael Francis Dube, William Monroe Coleman, III
-
Patent number: 8883065Abstract: Provided is a curable composition for imprints having good patternability and dry etching resistance. Disclosed is a curable composition for imprints comprising a polymerizable monomer (Ax) having a substituent having an aromatic group and having a molecular weight of 100 or more, and a photopolymerization initiator.Type: GrantFiled: December 2, 2009Date of Patent: November 11, 2014Assignee: FUJIFILM CorporationInventors: Kunihiko Kodama, Kyouhei Sakita, Hiroyuki Yonezawa
-
Patent number: 8877828Abstract: Provided is a method of producing a curable composition for imprints including (A) a polymerizable monomer, (B) a polymerization initiator, and (C) a solvent which is capable of effectively suppressing lifting or separation of patterns, excellent in coatability, and excellent in time-dependent stability. The method of producing a curable composition for imprints comprises preparing one species of liquid (D) which contains at least either one of the polymerizable monomer (A) and the polymerization initiator (B), passing the liquid (D) through a filter, and then adding the solvent (C).Type: GrantFiled: February 10, 2012Date of Patent: November 4, 2014Assignee: FUJIFILM CorporationInventors: Yuichiro Enomoto, Kunihiko Kodama, Shinji Tarutani
-
Patent number: 8653213Abstract: Hydrophobic coating compositions are provided as are processes to coat articles with the compositions. Extremely hydrophobic coatings are provided by the compositions. Compositions that include perfluorohexyl(meth)acrylate and a branched or high Tg monomer are provided as are articles coated with the polymerization product of the composition. Methods are also provided for forming hydrophobic coatings on articles.Type: GrantFiled: August 16, 2011Date of Patent: February 18, 2014Assignee: Cytonix, LLCInventor: James F Brown
-
Patent number: 8552083Abstract: The present invention relates to a radiation-curable composition having a refractive index less than 1.40 comprising (1) a curable perfluoropolyether oligomer having a structural formula selected from the group consisting of: and wherein R represents a hydrogen atom or a methyl group, wherein A represents a straight chained or branched alkylene group, wherein m represents an integer from 1 to 4, wherein the integers represented by m within individual —((CF2)m—O)n— repeat units can be the same or different, and wherein n represents an integer from 1 to 20; (2) a diluent; (3) a photo-initiator; and (4) an adhesion promoter; wherein the radiation-curable composition is free of compounds containing —CF3 groups.Type: GrantFiled: June 29, 2011Date of Patent: October 8, 2013Assignee: Ovation Polymer Technology and Engineered Materials, Inc.Inventors: Prasad Taranekar, Austin L. Schuman, Asis Banerjie
-
Patent number: 8552084Abstract: A process for preparing a pressure sensitive adhesive using a modified planetary roller extruder is described. The process in accordance with one aspect of the invention is a continuous process that includes introducing primary raw materials comprising a non-thermoplastic elastomer into a planetary roller extruder, introducing a heat-activatable crosslinker into the planetary roller extruder for mixing with the primary raw materials, and compounding the primary raw materials and the heat activatable crosslinker to form an adhesive composition while maintaining the temperature of the adhesive composition between about 25° C. and about 100° C. The non-thermoplastic elastomer is masticated during compounding and at least some of the heat-activatable crosslinker remains generally unactivated and is available for later activation.Type: GrantFiled: December 27, 2011Date of Patent: October 8, 2013Assignee: Intertape Polymer Corp.Inventors: John Kinch Tynan, Jr., Richard Walter St. Coeur, David Michael Kovach, Thomas Lombardo
-
Patent number: 8394870Abstract: Disclosed herein is a crosslinked fluoropolymer network formed by the free radical initiated crosslinking of a diacrylate fluoropolymer The diacrylate copolymer is of formula CH2?CR?COO—(CH2)n—R—(CH2)n—OOCR??CH2, wherein R is selected from the group consisting of i) an oligomer comprising copolymerized units of vinylidene fluoride and perfluoro(methyl vinyl ether), ii) an oligomer comprising copolymerized units of vinylidene fluoride and hexafluoropropylene, iii) an oligomer comprising copolymerized units of tetrafluoroethylene and perfluoro(methyl vinyl ether), and iv) an oligomer comprising copolymerized units of tetrafluoroethylene and a hydrocarbon olefin, R? is H or —CH3, n is 1-4 and wherein said oligomer has a number average molecular weight of 1000 to 25,000 daltons. The source of the free radicals may be a photoinitiator or an organic peroxide.Type: GrantFiled: July 16, 2009Date of Patent: March 12, 2013Assignees: E.I. du Pont de Nemours and Company, Le Centre National de la Recherche ScienceInventors: Ming-Hong Hung, Bruno Ameduri, Georgi Kostov
-
Patent number: 8353582Abstract: An ultraviolet curable inkjet recording ink of the present invention includes at least a colorant, a light-curable compound, a photopolymerization initiator, and at least one fluorine surfactant represented by the following formulae (1) or (2) as a surface tension regulator: where Rf is selected from CH2CF3 and CH2CF2CF3; n represents a value of 5 to 20; and each R1 represents a functional group capable of initiating an ultraviolet curing reaction and one of the two R1s in (1) may be hydrogen; where Rf is selected from CH2CF3 and CH2CF2CF3; l represents a value of 1 to 20; k and m each represent a value of 1 to 8; each R2 represents a functional group capable of initiating an ultraviolet curing reaction and one of the two R2s in (2) may be hydrogen; and R3 is selected from hydrogen and methyl.Type: GrantFiled: June 30, 2009Date of Patent: January 15, 2013Assignee: Ricoh Company, Ltd.Inventors: Hisashi Habashi, Michihiko Namba, Kiyofumi Nagal
-
Photocurable composition and process for producing molded product having fine pattern on its surface
Patent number: 8258201Abstract: To provide a photocurable composition whereby it is possible to obtain a cured product provided with both release property and high refractive index, and a process whereby it is possible to produce a molded product having a high refractive index and having on its surface a fine pattern having a reverse pattern of a mold precisely transferred. The photocurable composition comprising from 61 to 90 mass % of a compound (A) having a refractive index of at least 1.55 at a wavelength of 589 nm before curing and having at least two (meth)acryloyloxy groups, from 2 to 15 mass % of a compound (B) having fluorine atoms and at least one carbon-carbon unsaturated double bond (provided that compound (A) is excluded), from 5 to 35 mass % of a compound (C) having one (meth)acryloyloxy group (provided that compound (B) is excluded), and from 1 to 12 mass % of a photopolymerization initiator (D) (provided (A)+(B)+(C)+(D)=100 mass %).Type: GrantFiled: September 23, 2010Date of Patent: September 4, 2012Assignee: Asahi Glass Company, LimitedInventor: Yasuhide Kawaguchi -
Publication number: 20120213969Abstract: A functionally graded shape memory polymer (SMP) that has a range of transition temperatures that are spatially distributed in a gradient fashion within one single article. The SMP is formed by post-curing a pre-cured glassy SMP in a linear temperature gradient that imposes different vitrification temperature limits at different positions along the gradient. Utilizing indentation-based surface shape memory coupled with optical measurements of photoelastic response, the capability of this material to respond over a wide range of thermal triggers is correlated with the graded glass transition behavior. This new class of SMP offers great potential for such applications as passive temperature sensing and precise control of shape evolution during a thermally triggered shape recovery.Type: ApplicationFiled: February 21, 2012Publication date: August 23, 2012Applicant: SYRACUSE UNIVERSITYInventors: Patrick Mather, Pine Yang, Xiaofan Luo, Andrew M. DiOrio
-
Patent number: 8231973Abstract: Antireflective film articles and low refractive index coating compositions are described that comprises a fluorinated free-radically polymerizable polymeric (e.g. intermediate) material. The free-radically polymerizable fluorinated polymeric intermediate comprises the reaction product of i) at least one multi-functional free-radically polymerizable material having a fluorine content of at least 25 wt-%, and ii) optionally other multi-functional free-radically polymerizable material. The total amount of multi-functional materials is preferably at least about 25 wt-%.Type: GrantFiled: May 4, 2007Date of Patent: July 31, 2012Assignee: 3M Innovative Properties CompanyInventors: Marc D. Radcliffe, Thomas P. Klun, Lan H. Liu, Richard J. Pokorny, Suresh Iyer, Zai-Ming Qiu
-
Patent number: 8163813Abstract: To provide a photocurable composition from which a cured product excellent in mold release characteristics and mechanical strength can be obtained, and a method for producing a molded product excellent in durability, with a fine pattern having a reverse pattern of a mold precisely transferred on its surface. A photocurable composition 20 comprising from 15 to 60 mass % of a compound (A) which is an aromatic compound having at least two rings or an alicyclic compound having at least two rings and which has two (meth)acryloyloxy groups, from 5 to 40 mass % of a compound (B) having a fluorine atom and having at least one carbon-carbon unsaturated double bond (excluding the compound (A)), from 10 to 55 mass % of a compound (C) having one (meth)acryloyloxy group (excluding the compound (B)) and from 1 to 12 mass % of a photopolymerization initiator (D) (provided that (A)+(B)+(C)+(D)=100 mass %) is used.Type: GrantFiled: August 17, 2009Date of Patent: April 24, 2012Assignee: Asahi Glass Company, LimitedInventors: Yasuhide Kawaguchi, Kentaro Tsunozaki
-
Patent number: 8110612Abstract: A process for preparing a pressure sensitive adhesive using a modified planetary roller extruder is described. The process in accordance with one aspect of the invention includes introducing primary raw materials including a non-thermoplastic elastomer into a feeding section of the modified planetary roller extruder, conveying the raw materials from the feeding section to a compounding section of the modified planetary roller extruder, continuously mixing the primary raw materials in the compounding section to produce a homogeneous adhesive composition. The adhesive composition may be applied to a web-form material. The compounding section of the modified planetary roller extruder includes a main spindle surrounded by and intermeshed with a plurality of planetary spindles at least one of which is a double transversal mixing spindle having a plurality of back-cut helical flights.Type: GrantFiled: February 5, 2007Date of Patent: February 7, 2012Assignee: Intertape Polymer Corp.Inventors: John Kinch Tynan, Jr., Richard Walter St. Coeur, David Michael Kovach, Thomas Lombardo
-
Patent number: 8007878Abstract: An antireflection film comprising a support and a low refractive index layer prepared by coating a coating composition containing the following components: (A) a fluorine-containing polymer, a principal chain of which is made of only carbon atoms and which contains at least one fluorine-containing vinyl monomer polymerization unit and at least one hydroxyl group-containing vinyl monomer polymerization unit, wherein a content of the hydroxyl group-containing vinyl monomer polymerization unit exceeds 20% by mole, provided that the polymer does not have a polysiloxane structure in the principal chain; (B) a crosslinking agent capable of reacting with a hydroxyl group; and (C) a compound containing two or more (meth)acryloyl groups in one molecule thereof.Type: GrantFiled: August 3, 2006Date of Patent: August 30, 2011Assignee: Fujifilm CorporationInventors: Hiroyuki Yoneyama, Masaki Noro, Yasuhiro Okamoto
-
Patent number: 7999013Abstract: Hydrophobic coating compositions are provided as are processes to coat articles with the compositions. Extremely hydrophobic coatings are provided by the compositions. Durable, weatherable and scratch-resistant coatings are provided by compositions comprising a trifluoromethyl-containing component and a hardenable material. Weatherable coatings are also provided by compositions comprising a mobile non-volatile fluorinated component and a hardenable material. Processes are also provided for forming hydrophobic coatings on articles.Type: GrantFiled: June 16, 2010Date of Patent: August 16, 2011Assignee: Cytonix, LLCInventor: James F. Brown
-
Patent number: 7883764Abstract: Disclosed is a resinous molded article which has a fine structure of a nanometer level and includes a material containing a polymer of a polymerizable organic fluorocompound. The polymer is formed from, for example, a monomeric precursor composition containing a methacrylate and/or an acrylate in combination with a fluorine-containing photopolymerizable monomeric precursor composition miscible with the former composition.Type: GrantFiled: October 16, 2007Date of Patent: February 8, 2011Assignee: Hitachi Chemical Company, Ltd.Inventor: Kenji Murao
-
Patent number: 7705064Abstract: The present invention is directed to reaction products prepared from at least one Michael addition donor material including two or more active methylene hydrogens; and at least one material capable of reacting with a Michael addition donor, the material having one Michael addition acceptor and at least one functional group selected from the group consisting of hydroxy, hydroxyalkyl, vinyl ether, amino, aminoalkyl, carboxy, carboxyalkyl, cyano, and cyanoalkyl groups; or reaction products prepared from (a) at least one Michael addition donor material comprising at least one Michael Addition donor group selected from the group consisting of cyano functional groups and phosphono functional groups; and (b) at least one material capable of reacting with the at least one Michael addition donor group, the material having at least one Michael addition acceptor, wherein the above reaction products are capable of forming free radicals upon exposure to actinic radiation; as well as compositions, and processes for makingType: GrantFiled: July 23, 2007Date of Patent: April 27, 2010Assignee: Henkel CorporationInventors: Anthony F. Jacobine, John G. Woods, Joel D. Schall, Steven T. Nakos, Andrew D. Messana, David M. Glaser
-
Patent number: 7595353Abstract: The invention provides a photocurable polymer composition having a fluorine-containing polymer and a fluorine-free polymer, and preferably further having a polymerizable double bond-containing compound and a photopolymerization initiator. The fluorine-containing polymer preferably includes a fluorosilsesquioxane skeleton.Type: GrantFiled: September 28, 2006Date of Patent: September 29, 2009Assignee: Chisso CorporationInventors: Hisanobu Minamisawa, Mikio Yamahiro, Akira Meguro
-
Patent number: 7572839Abstract: A seal ring (10) of the present invention seals operating oil hermetically and is attached to an annular seal ring groove (16) provided on an outer circumference of a shaft member (12). The seal ring (10) includes fluororesin, modified fluororesin formed by being irradiated with 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, and synthetic resin having a surface energy ranging from +0 N/cm to 20˜10?5 N/cm inclusive of that of the operating oil.Type: GrantFiled: September 29, 2004Date of Patent: August 11, 2009Assignees: Nissan Motor Co., Ltd., Hitachi Cable, Ltd.Inventors: Tomohito Ota, Tomihito Hashimoto, Yasuaki Yamamoto, Hiroo Kusano
-
Patent number: 7566754Abstract: The invention relates to novel crosslinkable copolymers which are obtainable by (a) copolymerizing at least one hydrophilic monomer having one ethylenically unsaturated double bond and at least one crosslinker comprising two or more ethylenically unsaturated double bonds in the presence of a chain transfer agent having a functional group; and (b) reacting one or more functional groups of the resulting copolymer with an organic compound having an ethylenically unsaturated group. The crosslinkable copolymers of the invention are especially useful for the manufacture of biomedical mouldings, for example ophthalmic mouldings such as in particular contact lenses.Type: GrantFiled: August 10, 2007Date of Patent: July 28, 2009Assignee: Novartis AGInventors: Beat Müller, Alain Laurent, Veerle Coessens, Aaldert Rens Molenberg
-
Patent number: 7521486Abstract: Fluoropolymers are made by admixing tetrafluoroethylene, hexfluoropropylene, and vinylidene fluoride; reacting the reaction admixture to generate a set of fluoropolymeric oligomers; irradiating the fluoropolymeric oligomeric precursor admixture (preferably with electron beam radiation) to form free radical sites on individual fluoropolymeric oligomers of the set and generate thereby a set of free radical oligomer derivatives in the fluoropolymeric oligomeric precursor admixture; and reacting the fluoropolymeric oligomeric precursor admixture to derive the fluoropolymer compound from the free radical oligomer derivatives. In a second approach, fluoropolymers are made by admixing tetrafluoroethylene, hexfluoropropylene, and vinylidene fluoride and irradiating the admixture.Type: GrantFiled: May 14, 2007Date of Patent: April 21, 2009Assignee: Freudenberg-NOK General PartnershipInventor: Edward Hosung Park
-
Patent number: 7514481Abstract: 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: GrantFiled: January 29, 2007Date of Patent: April 7, 2009Assignee: 3M Innovative Properties CompanyInventors: Michael A. Yandrasits, Steven J. Hamrock, Naiyong Jing
-
Patent number: 7514480Abstract: 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: GrantFiled: June 21, 2005Date of Patent: April 7, 2009Assignee: Arkema Inc.Inventors: Nafih Mekhilef, Ramin Amin-Sanayei
-
Publication number: 20090081375Abstract: A process for producing an overprint is provided that includes a step of preparing a printed material printed on a printing substrate, a step of coating the printed material with a photocurable composition, and a step of photocuring the photocurable composition, the photocurable composition comprising (I) a fluorine-containing polymer having an ethylenically unsaturated group, (II) an ethylenically unsaturated compound, and (III) a photopolymerization initiator. There are also provided an overprint produced by the production process, and the photocurable composition.Type: ApplicationFiled: September 8, 2008Publication date: March 26, 2009Applicant: FUJIFILM CorporationInventor: Ryuki KAKINO
-
Patent number: 7482393Abstract: 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: GrantFiled: December 29, 2004Date of Patent: January 27, 2009Assignee: Shamrock Technologies Inc.Inventors: Charles A. Cody, William Neuberg, Manshi Sui, Youssef Awad
-
Patent number: 7439279Abstract: 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: GrantFiled: May 13, 2005Date of Patent: October 21, 2008Assignee: Asahi Glass Company, LimitedInventors: Satoshi Kondo, Daisuke Shirakawa, Toshihiko Higuchi, Hirotsugu Yamamoto
-
Publication number: 20080016644Abstract: A surface-modified blade rubber includes a surface modified by being subjected to irradiation treatment that generates radical active sites in the blade rubber and polymerization for graft polymerization starting from a generated radical active site. A method for modifying a blade rubber surface includes subjecting rubber of a blade rubber to irradiation treatment that generates radical active sites and polymerization for graft polymerization starting from a generated radical active site.Type: ApplicationFiled: July 13, 2007Publication date: January 24, 2008Applicant: MITSUBA CORPORATIONInventors: Norihito Mizote, Akio Katakai, Masao Tamada
-
Patent number: 7291655Abstract: A polymerization process with elevated productivity using a coordination catalyst, wherein electromagnetic radiation is applied during polymerization. The irradiation of light greatly increases the activity of the coordination catalyst.Type: GrantFiled: May 29, 2002Date of Patent: November 6, 2007Assignee: Borealis Technology OyInventors: Karl-Heinz Reichert, Annette Wittebrock, Kalle Kallio
-
Patent number: 7282525Abstract: 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: GrantFiled: December 27, 2001Date of Patent: October 16, 2007Assignee: Mitsui Chemicals, Inc.Inventors: Hiroyuki Kurata, Hideto Matsuoka
-
Patent number: 7265162Abstract: 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: GrantFiled: November 13, 2003Date of Patent: September 4, 2007Assignee: 3M Innovative Properties CompanyInventors: Michael A. Yandrasits, Steven J. Hamrock, Klaus Hintzer, Arne Thaler, Tatsuo Fukushi, Naiyong Jing, Kai Helmut Lochhaas
-
Patent number: 7241817Abstract: 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: GrantFiled: June 2, 2004Date of Patent: July 10, 2007Assignee: Arkema FranceInventors: Anthony Bonnet, Barbara Ramfel, Fabrice Chopinez, Karine Triballier, Michael Werth, Thierry Pascal
-
Patent number: 7230038Abstract: Fluoropolymers are made by admixing tetrafluoroethylene, hexfluoropropylene, and vinylidene fluoride; reacting the reaction admixture to generate a set of fluoropolymeric oligomers; irradiating the fluoropolymeric oligomeric precursor admixture (preferably with electron beam radiation) to form free radical sites on individual fluoropolymeric oligomers of the set and generate thereby a set of free radical oligomer derivatives in the fluoropolymeric oligomeric precursor admixture; and reacting the fluoropolymeric oligomeric precursor admixture to derive the fluoropolymer compound from the free radical oligomer derivatives. In a second approach, fluoropolymers are made by admixing tetrafluoroethylene, hexfluoropropylene, and vinylidene fluoride and irradiating the admixture.Type: GrantFiled: June 30, 2004Date of Patent: June 12, 2007Assignee: Freudenberg-NOK General PartnershipInventor: Edward Hosung Park
-
Patent number: 7220788Abstract: 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: GrantFiled: February 27, 2004Date of Patent: May 22, 2007Assignee: Nichias CorporationInventors: Naoya Kuzawa, Mitsuyuki Nakano, Hitoshi Ogura, Masayuki Saito
-
Patent number: 7179847Abstract: 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: GrantFiled: November 13, 2003Date of Patent: February 20, 2007Assignee: 3M Innovative Properties CompanyInventors: Michael A. Yandrasits, Steven J. Hamrock, Naiyong Jing
-
Patent number: 7112614Abstract: 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: GrantFiled: December 8, 2003Date of Patent: September 26, 2006Assignee: 3M Innovative Properties CompanyInventors: Naiyong Jing, Steven J. Hamrock
-
Patent number: 7074841Abstract: 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: GrantFiled: November 13, 2003Date of Patent: July 11, 2006Inventors: Michael A. Yandrasits, Steven J. Hamrock, Werner M. Grootaert, Miguel A. Guerra, Naiyong Jing
-
Patent number: 7060738Abstract: 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: GrantFiled: December 11, 2003Date of Patent: June 13, 2006Assignee: 3M Innovative Properties CompanyInventors: Naiyong Jing, Steven J. Hamrock, Michael A. Yandrasits
-
Patent number: 7030171Abstract: The objective of the present invention is to provide a production method by which a polymer of a functional group-terminated vinyl monomer can be easily and practically produced. Further, it is another object of the present invention to provide a functional group-terminated vinyl polymer which is useful as a material for the production of various functional products. The first aspect of the present invention is concerned with a production method of a functional group-terminated vinyl polymer comprising a step of synthesizing a halogen atom-terminated vinyl polymer by the radical polymerization reaction of a vinyl monomer in the presence of a halogen compound and a step of introducing a functional group to a terminus by substituting a functional group-containing group for the terminal halogen atom of said vinyl polymer.Type: GrantFiled: October 31, 2003Date of Patent: April 18, 2006Assignee: Sekisui Chemical Co., Ltd.Inventors: Takeshi Wakiya, Takamaro Kakehi
-
Patent number: 6833393Abstract: 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: GrantFiled: December 4, 2001Date of Patent: December 21, 2004Assignee: Asahi Glass Company, LimitedInventors: Kenji Ishizeki, Hirotsugu Yamamoto, Yuichi Yamamoto
-
Patent number: 6391975Abstract: Chlorotrifluoroethylene (CTFE) thermoplastic perhalogenated polymers, formed by the following polymer components: (I) 10-90% by weight of a CTFE homopolymer and (II) 90-10% by weight of a CTFE copolymer modified with comonomer (a) selected from one or more perfluoroalkyl vinylethers having the formula: Rf—O—CF═CF2 wherein: Rf is a C2-C5 perfluoroalkyl group, resulting in the final polymer (I)+(II), the amount of (a) being from 0,2 to 5% by moles and the CTFE the remaining part to 100% by moles.Type: GrantFiled: July 7, 2000Date of Patent: May 21, 2002Assignee: Ausimont S.p.A.Inventors: Julio A. Abusleme, Claudia Manzoni
-
Patent number: 6348517Abstract: A method of preparing a sterile article is disclosed. A polymer having a halogen-containing repeating unit is prepared that contains about 0.Type: GrantFiled: September 1, 2000Date of Patent: February 19, 2002Assignee: Oxy Services, Inc.Inventors: Qi Wang, Sandor Nagy
-
Publication number: 20010053502Abstract: This invention relates to a novel class of halofluorinated acrylates and more particularly to chlorofluorinated or bromofluorinated acrylates characterized by a chlorofluorinated or bromofluorinated alkylene moiety with acrylate functions at both terminals. These chlorofluorinated acrylates may be photocured in the presence of a photoinitiator into transparent polymers useful as optical waveguiding materials.Type: ApplicationFiled: June 13, 2001Publication date: December 20, 2001Inventors: Chengjiu Wu, Baopei Xu, Jianhui Shan, James T. Yardley
-
Patent number: 6316519Abstract: Synthesis of linear acrylic polymers and copolymers having controlled molecular weight by the photoinitiated free radical polymerization of vinyl monomers in the presence of chain transfer agents to produce polymers useful in coating compositions and the like, including printing inks.Type: GrantFiled: August 19, 1999Date of Patent: November 13, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: Charles Thomas Berge, Vincent Desobry
-
Patent number: 6314225Abstract: A copolymer containing N-(halogenated phenyl) maleimide units or N-(halogenated phenyl) bismaleimide units and one or more second units selected from halogenated acrylates, halogenated styrenes, halogenated vinyl ether, halogenated olefins, halogenated vinyl isocyanates, halogenated N-vinyl amides, halogenated allyls, halogenated propenyl ethers, halogenated methacrylates, halogenated maleates, halogenated itaconates, and halogenated crotonates, is useful to form optical devicesType: GrantFiled: November 23, 1999Date of Patent: November 6, 2001Assignee: Corning IncorporatedInventor: Jianguo Wang
-
Patent number: 6107364Abstract: Described are a polymerizable composition comprising methyl styrene monomer, polymers comprising monomeric units derived from methyl styrene monomers, and optical products comprising these polymers.Type: GrantFiled: May 9, 1997Date of Patent: August 22, 2000Assignee: 3M Innovative Properties CompanyInventors: Bettie C. Fong, David B. Olson
-
Patent number: 6090865Abstract: Compounds of formula (I), ##STR1## wherein X is CH, C--CH.sub.3, C--Cl, C--O--C.sub.1 -C.sub.8 alkyl or N; R is C.sub.1 -C.sub.6 alkyl, benzyl, CH.sub.2 COOR.sub.3 or a group (a); R.sub.1 is C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.12 alkyl, halogen, NO.sub.2, benzyloxy or phenyloxy, wherein the phenyl ring in the benzyloxy or phenyloxy group is unsubstituted or substituted by C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.12 alkyl, halogen or CF.sub.3 ; R.sub.2 is C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.12 alkyl, benzyloxy or phenyloxy, wherein the phenyl ring in the benzyloxy or phenyloxy group is unsubstituted or substituted by C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.12 alkyl, halogen or CF.sub.3 ; R.sub.3 is hydrogen, C.sub.1 -C.sub.12 alkyl or benzyl; Y is unsubstituted or C.sub.1 -C.sub.6 alkoxy-substituted C.sub.1 -C.sub.6 alkyl, or Y is C.sub.1 -C.sub.6 alkoxy, halogen, CF.sub.3, NO.sub.2, benzyloxy or phenyloxy, wherein the phenyl ring in the benzyloxy or phenyloxy group is unsubstituted or substituted by C.Type: GrantFiled: October 26, 1998Date of Patent: July 18, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Christopher Curtis Dudman, Allan Francis Cunningham, Martin Kunz
-
Patent number: 6025407Abstract: Disclosed is a process for polymerizing vinyl chloride monomer in the presence of light. A mixture is formed of liquid vinyl chloride monomer, preferably about 10 to about 250 ppm of a metallocene catalyst, about 1 to about 2000 moles of an aluminum-containing cocatalyst per mole of catalyst, and up to about 500 moles of a Lewis base per mole of aluminum in the cocatalyst. Selected alkyl groups from the aluminum-containing cocatalyst can be placed on the ends of the poly (vinyl chloride) chains.Type: GrantFiled: October 30, 1997Date of Patent: February 15, 2000Assignee: Occidental Chemical CorporationInventors: Sandor M. Nagy, Ramesh Krishnamurti, Mary K. Cocoman, Walter M. Opalinski, Thomas F. Smolka
-
Patent number: 5932626Abstract: Described are optical products comprising a base and an optical layer. The optical layer is prepared from a polymerizable composition comprising an alkyl-substituted brominated phenolic ester(meth)acrylate monomer.Type: GrantFiled: May 9, 1997Date of Patent: August 3, 1999Assignee: Minnesota Mining and Manufacturing CompanyInventors: Bettie C. Fong, David B. Olson
-
Patent number: 5908874Abstract: A polymerizable composition has added thereto a fluorochemical in sufficient quantities to reduce the melting temperature of the composition compared with that of the composition absent the fluorochemical.Type: GrantFiled: June 18, 1996Date of Patent: June 1, 1999Assignee: 3M Innovative Properties CompanyInventors: Bettie C. Fong, Myles L. Brostrom
-
Patent number: 5872157Abstract: A process for making oxidized olefins is disclosed. Specifically, the process comprises providing an olefin and oxygen in combination in a reaction medium comprising carbon dioxide, and then oxidizing the olefin in the reaction medium to make the oxidized olefin. Preferably, a perfluoropolyether is produced by the process.Type: GrantFiled: January 30, 1996Date of Patent: February 16, 1999Assignee: The University of North Carolina at Chapel HillInventors: Joseph M. DeSimone, Timothy J. Romack