Halogenated Patents (Class 524/758)
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Patent number: 10240047Abstract: The present invention provides a curable composition having an excellent permeability to a porous substrate and a sufficient strength for use as a coating film, and also having a suitable curing time (set time), accordingly the curable composition having a pot life from the application until the completion of the permeation to pore portions. Particularly, the present invention also provides a favorable coating agent for surface reinforcement coating of a porous substrate. These objects can be achieved by using a curable composition containing the following (A) and (B): (A) a cyanoacrylate compound; and (B) a hydrofluoroether having such a structure that the number of carbon atoms substituted only with fluorine in the molecule is 1 or more to 6 or less, and the number of carbon atoms in the molecule is less than 7.Type: GrantFiled: March 3, 2017Date of Patent: March 26, 2019Assignee: THREEBOND CO., LTD.Inventor: Koji Yamada
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Patent number: 8969437Abstract: The invention provides a compound which is useful in production of a fluoropolymer and easy to be removed from the produced fluoropolymer, a method of producing the compound, and a method of producing a fluoropolymer using the compound. The invention provides a compound which is represented by Rf1—CH2O—CF2—CHF—Rf2—X, wherein Rf1 represents a fluoroalkyl group containing 1 to 5 carbon atoms, Rf2 represents a fluoroalkylene group containing 1 to 3 carbon atoms, X represents —COOM or —SO3M, and M represents one of H, K, Na, and NH4.Type: GrantFiled: January 18, 2013Date of Patent: March 3, 2015Assignee: Daikin Industries, Ltd.Inventors: Nobuhiko Tsuda, Akinari Sugiyama
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Publication number: 20140287248Abstract: Fluorinated coatings having a lubricious additive, articles with the fluorinated coatings, and methods of making articles with the fluorinated coatings are provided. More specifically, the fluorinated coatings are prepared from a curable coating composition that includes both a fluorinated silane and a fluorinated polyether oil. The curable coating composition is typically applied adjacent to a siliceous substrate and then cured. The resulting cured articles can have an outer surface that has a good tactile response, that is abrasion resistant, that is easy to clean, or a combination thereof.Type: ApplicationFiled: November 2, 2012Publication date: September 25, 2014Inventors: Richard M. Flynn, Erik D. Olson, Kevin J. Bechtold, Michael W. Bench
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Publication number: 20140200310Abstract: The present invention aims to provide a novel method for producing an aqueous dispersion containing non-melt-processable polytetrafluoroethylene particles. The present invention relates to a method for producing an aqueous dispersion containing non-melt-processable polytetrafluoroethylene particles, the method including polymerizing tetrafluoroethylene in an aqueous medium in the presence of perfluoro hexanoic acid or its salt.Type: ApplicationFiled: August 27, 2012Publication date: July 17, 2014Applicant: DAIKIN INDUSTRIES, LTD.Inventors: Takahiro Taira, Taku Yamanaka, Yoshinori Nanba, Atsuko Tanaka, Makoto Ono, Nobuhiko Tsuda, Taketo Kato
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Publication number: 20140094564Abstract: There is provided an article prepared from a fluoroelastomer, the fluoroelastomer being derived from an emulsion, the emulsion comprising a fluorinated emulsifier represented by the formula F—(CF2)t—[O(CF2)n]m—O—(CHF)o—(CF2)p—X.Type: ApplicationFiled: September 20, 2013Publication date: April 3, 2014Applicant: 3M INNOVATIVE PROPERTIES COMPANYInventors: Klaus Hintzer, Kai H. Lochhaas, Michael Jürgens, Harald Kaspar, Tilman C. Zipplies, André Streiter
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Patent number: 8633278Abstract: The invention relates to novel, stable bi-molecular cationic inverse emulsion polymers (W/O) with both different molecular weights and cationic activities that are assembled via an “in situ” emulsion polymerization of a high molecular weight cationic polymer in the presence of a low molecular weight polymer in the aqueous phase. The low molecular cationic polymer is produced in a pre-polymerization in solution. The novel, stable cationic water-in-oil emulsion is easy invertible and useful as flocculant, dewatering aid and retention aid in papermaking.Type: GrantFiled: April 9, 2010Date of Patent: January 21, 2014Assignee: Hercules IncorporatedInventors: Markus Broecher, Charlotta Kanto Oeqvist, Nathalie Sieverling, Georg Linneweber
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Patent number: 8623957Abstract: Method of making fluoropolymers by emulsion polymerization of one or more fluorinated monomers in an aqueous phase in the presence of a fluorinated emulsifier, said method comprises adding a doping agent in a weight ratio with respect to the emulsifier of from about 1:2 to about 1:20, said doping agent has a melting point of equal or less than 30° C. and a boiling point of at least about 100° C. and is selected from the group consisting of fluorinated cyclic hydrocarbons, fluorinated polyoxyalkenes, fluorinated alkenes and fluorinated polyoxyalkenes.Type: GrantFiled: August 15, 2008Date of Patent: January 7, 2014Assignee: 3M Innovative Properties CompanyInventors: Klaus Hintzer, Michael Juergens, Harald Kaspar, Kai Helmut Lochhaas, André Streiter, Tilman C. Zipplies, Werner Schwertfeger
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Patent number: 8536269Abstract: The present invention provides peroxidic fluoropolyether and a fluorine-containing dispersion obtained from polymerization of fluorine-containing monomers in the presence of peroxidic fluoropolyether as a surfactant. The peroxidic fluoropolyether can be used as surfactant for producing aqueous dispersion of fluorine-containing monomer in place of PFOA or the salts thereof. Thus the amount of PFOA or the salts thereof is reduced and the natural environment is protected. In addition, applying peroxidic fluoropolyether as surfactant and combining it with adjuvants, such as initiator, can induce the reaction moderate and can be beneficial to the polymerization control, thus reducing the amount of initiator or shortening the reaction time.Type: GrantFiled: August 15, 2008Date of Patent: September 17, 2013Assignee: Nova-Duct Technologies Pty LtdInventors: Xueduan Xie, Jun Qu, Rong Bai, Jianxin Zhang, Xucang Yang, Bo Chen, Jingang Zhang, Ming Zhang, Xianquan Hu, Yu Cheng
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Publication number: 20120322941Abstract: The present invention provides a tetrafluoroethylene polymer aqueous dispersion obtained by carrying out a TFE polymerization in an aqueous medium in the presence of a fluorovinyl group-containing emulsifier, wherein the TFE polymer aqueous dispersion contains a particle comprising a TFE polymer dispersed in the aqueous medium, the fluorovinyl group-containing emulsifier comprises a fluorovinyl group-containing compound, and the TFE polymer aqueous dispersion has a fluorine-containing surfactant content of not higher than 1000 ppm by mass.Type: ApplicationFiled: August 30, 2012Publication date: December 20, 2012Applicant: DAIKIN INDUSTRIES, LTD.Inventors: Nobuhiko TSUDA, Yoshinori NANBA, Yasuhiko SAWADA, Tetsuo SHIMIZU
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Publication number: 20120283382Abstract: A process for manufacturing a dispersions of a vinylidene fluoride (VDF) thermoplastic polymer [polymer (F)], said process comprising polymerizing VDF in an aqueous phase comprising: at least one surfactant selected from the group consisting of non-fluorinated surfactants [surfactant (HS)] and fluorinated surfactants having a molecular weight of less than 400 [surfactant (FS)]; and at least one functional (per)fluoropolyether (functional PFPE) comprising at least one (per)fluoropolyoxyalkylene chain [chain (R?F)] and at least one functional group, said functional PFPE having a number average molecular weight of at least 1000 and a solubility in water of less than 1% by weight at 25° C., wherein said functional PFPE is present in the aqueous phase in an amount of 0.001 to 0.3 g/l.Type: ApplicationFiled: December 15, 2010Publication date: November 8, 2012Applicant: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.Inventors: Fabrizio Spada, Bradley Lane Kent
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Publication number: 20120077931Abstract: A process comprising polymerizing at least one fluorinated monomer in an aqueous medium containing initiator and polymerization agent to form an aqueous dispersion of particles of fluoropolymer, the polymerization agent comprising: fluoropolyether acid or salt thereof having a number average molecular weight of at least about 800 g/mol; and fluorosurfactant having the formula: [R1—On-L-A?]Y+ wherein: R1 is a linear or branched partially or fully fluorinated aliphatic group which may contain ether linkages; n is 0 or 1; L is a linear or branched alkylene group which may be nonfluorinated, partially fluorinated or fully fluorinated and which may contain ether linkages; A? is an anionic group selected from the group consisting of carboxylate, sulfonate, sulfonamide anion, and phosphonate; and Y+ is hydrogen, ammonium or alkali metal cation; with the proviso that the chain length of R1—On-L- is not greater than 6 atoms.Type: ApplicationFiled: December 7, 2011Publication date: March 29, 2012Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: PAUL DOUGLAS BROTHERS, Subhash Vishnu Gangal
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Publication number: 20120004365Abstract: A composition comprising a mixture of fluoropolyether acids or salts having a number average value of about 800 to about 2500 g/mol. The amount of fluoropolyether acids or salt in the mixture having a molecular weight of not more than 500 g/mol is not more than 50 ppm by weight of the total amount of fluoropolyether acids or salts in the mixture. The amount of fluoropolyether acids or salts in the mixture having a molecular weight of 2500 g/mol or greater is not more than 40% by weight of the total amount of fluoropolyether acids or salts in the mixture. Preferably the fluoropolyether acids or salts comprise an anionic group selected from the group consisting of carboxylate, sulfonate, sulfonamide anion and phosphonate. Also disclosed is an aqueous dispersion polymerization process for fluoropolymer manufacture employing polymerization agent comprising the specified mixture of fluoropolyether acids or salts.Type: ApplicationFiled: September 13, 2011Publication date: January 5, 2012Applicant: E.I. DU PONT DE NEMOURS AND COMPANYInventors: Paul Douglas Brothers, Subhash Vishnu Gangal, Gregory Allen Chapman, Jon Lee Howell, Adam Paul Smith
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Publication number: 20110294951Abstract: Method of making fluoropolymers by emulsion polymerization of one or more fluorinated monomers in an aqueous phase in the presence of a fluorinated emulsifier, said method comprises adding a doping agent in a weight ratio with respect to the emulsifier of from about 1:2 to about 1:20, said doping agent has a melting point of equal or less than 30° C. and a boiling point of at least about 100° C. and is selected from the group consisting of fluorinated cyclic hydrocarbons, fluorinated polyoxyalkenes, fluorinated alkenes and fluorinated polyoxyalkenes.Type: ApplicationFiled: August 15, 2008Publication date: December 1, 2011Inventors: Klaus Hintzer, Michael Juergens, Harald Kaspar, Kai Helmut Lochhaas, André Streiter, Tilman C. Zipplies, Werner Schwertfeger
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Publication number: 20110207880Abstract: The present invention provides peroxidic fluoropolyether and a fluorin-containing dispersion obtained from polymerization of fluorin-containing monomers in the presence of peroxidic fluoropolyether as a surfactant. The peroxidic fluoropolyether can be used as surfactant for producing aqueous dispersion of fluorin-containing monomer in place of PFOA or the salts thereof. Thus the amount of PFOA or the salts thereof is reduced and the natural environment is protected. In addition, applying peroxidic fluoropolyether as surfactant and combining it with adjuvants, such as initiator, can induce the reaction moderate and can be beneficial to the polymerization control, thus reducing the amount of initiator or shortening the reaction time.Type: ApplicationFiled: August 15, 2008Publication date: August 25, 2011Applicant: Nova-Duet Technologies, Pty. Ltd.Inventors: Xueduan Xie, Jun Qu, Rong Bai, Jianxin Zhang, Xucang Yang, Bo Chen, Jingang Zhang, Ming Zhang, Xianquan Hu, Yu Cheng
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Patent number: 7897682Abstract: A process for polymerizing at least one fluorinated monomer in an aqueous medium in the presence of initiator and polymerization agent to form an aqueous dispersion of particles of fluoropolymer having a fluoropolymers solids content of at least about 10% by weight. The polymerization agent is a combination of fluoropolyether acid or salt thereof and hydrocarbon surfactant. The aqueous medium contains less than about 300 ppm of perfluoroalkane carboxylic acid or salt fluorosurfactants. The process is preferably performed without adding polymer seed prior to polymerization kick-off.Type: GrantFiled: November 9, 2007Date of Patent: March 1, 2011Assignee: E. I. du Pont de Nemours and CompanyInventors: Paul Douglas Brothers, Subhash Vishnu Gangal
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Publication number: 20110015342Abstract: To provide a fluorinated elastic copolymer having high crosslinkability, having high flowability and excellent in the compression set and the resistance to bases, and its production process. A process for producing a fluorinated elastic copolymer, which comprises copolymerizing (a) tetrafluoroethylene and (b) propylene and as the case requires, (c) a perfluoro(alkyl vinyl ether) in the presence of an iodine compound represented by the formula RI2 (wherein R is a hydrocarbon group or perfluoroalkyl group having at least 3 carbon atoms) at a temperature of from 0° C. to 50° C., and a fluorinated elastic copolymer obtained by the production process.Type: ApplicationFiled: September 28, 2010Publication date: January 20, 2011Applicant: ASAHI GLASS COMPANY, LIMITEDInventors: Takehiro KOSE, Mitsuru Seki, Hiroshi Funaki, Yasuhiko Matsuoka
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Publication number: 20100218982Abstract: It is an object of the present invention to provide an epoxy resin composition containing an epoxy compound, a low-molecular-weight phenol-modified polyphenylene ether and a cyanate compound as essential components, the epoxy resin composition having excellent dielectric characteristics and exhibiting high heat resistance while maintaining flame retardancy. To achieve this object, the epoxy resin composition of the present invention is a thermosetting resin composition composed of a resin varnish containing (A) an epoxy compound having a number-average molecular weight of 1000 or less and containing at least two epoxy groups in the molecule without containing any halogen atoms, (B) a polyphenylene ether having a number-average molecular weight of 5000 or less, (C) a cyanate ester compound, (D) a curing catalyst and (E) a halogen flame retardant, wherein all of the components (A) to (C) are dissolved in the resin varnish, while the component (E) is dispersed without being dissolved in the resin varnish.Type: ApplicationFiled: June 30, 2008Publication date: September 2, 2010Applicant: PANASONIC ELECTRIC WORKS CO., LTD.Inventors: Hiroaki Fujiwara, Masao Imai, Yuki Kitai
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Publication number: 20100152378Abstract: A process comprising polymerizing at least one fluorinated monomer in an aqueous medium containing initiator and polymerization agent to form an aqueous dispersion of particles of fluoropolymer, the polymerization agent comprising: fluoropolyether acid or salt thereof having a number average molecular weight of at least about 800 g/mol; and fluorosurfactant having the formula: [R1—On-L-A?]Y+ wherein: R1 is a linear or branched partially or fully fluorinated aliphatic group which may contain ether linkages; n is 0 or 1; L is a linear or branched alkylene group which may be nonfluorinated, partially fluorinated or fully fluorinated and which may contain ether linkages; A? is an anionic group selected from the group consisting of carboxylate, sulfonate, sulfonamide anion, and phosphonate; and Y+ is hydrogen, ammonium or alkali metal cation; with the proviso that the chain length of R1—On-L- is not greater than 6 atoms.Type: ApplicationFiled: February 25, 2010Publication date: June 17, 2010Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: Paul Douglas Brothers, Subhash Vishnu Gangal
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Publication number: 20100152379Abstract: A process comprising polymerizing at least one fluorinated monomer in an aqueous medium containing initiator and polymerization agent to form an aqueous dispersion of particles of fluoropolymer, the polymerization agent comprising: fluoropolyether acid or salt thereof having a number average molecular weight of at least about 800 g/mol; and fluorosurfactant having the formula: [R1—On-L-A?]Y+ wherein: R1 is a linear or branched partially or fully fluorinated aliphatic group which may contain ether linkages; n is 0 or 1; L is a linear or branched alkylene group which may be nonfluorinated, partially fluorinated or fully fluorinated and which may contain ether linkages; A? is an anionic group selected from the group consisting of carboxylate, sulfonate, sulfonamide anion, and phosphonate; and Y+ is hydrogen, ammonium or alkali metal cation; with the proviso that the chain length of R1—On-L- is not greater than 6 atoms.Type: ApplicationFiled: February 25, 2010Publication date: June 17, 2010Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: Paul Douglas Brothers, Subhash Vishnu Gangal
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Publication number: 20090281241Abstract: A composition comprising a mixture of fluoropolyether acids or salts having a number average value of about 800 to about 2500 g/mol. The amount of fluoropolyether acids or salt in the mixture having a molecular weight of not more than 500 g/mol is not more than 50 ppm by weight of the total amount of fluoropolyether acids or salts in the mixture. The amount of fluoropolyether acids or salts in the mixture having a molecular weight of 2500 g/mol or greater is not more than 40% by weight of the total amount of fluoropolyether acids or salts in the mixture. Preferably the fluoropolyether acids or salts comprise an anionic group selected from the group consisting of carboxylate, sulfonate, sulfonamide anion and phosphonate. Also disclosed is an aqueous dispersion polymerization process for fluoropolymer manufacture employing polymerization agent comprising the specified mixture of fluoropolyether acids or salts.Type: ApplicationFiled: May 6, 2009Publication date: November 12, 2009Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: Paul Douglas Brothers, Subhash Vishnu Gangal, Gregory Allen Chapman, Jon Lee Howell, Adam Paul Smith
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Patent number: 7375158Abstract: A thermoconductive curable liquid polymer composition including (A) a curable liquid polymer, (B) a filler made from a thermally-elongatable shape-memory alloy, and (C) a thermoconductive filler other than (B). A semiconductor device having a semiconductor element glued or coated with the thermoconductive curable liquid polymer composition.Type: GrantFiled: May 29, 2003Date of Patent: May 20, 2008Assignee: Dow Corning Toray Silicone Company, Ltd.Inventors: Hiroki Ishikawa, Katsutoshi Mine, Kimio Yamakawa, Kazumi Nakayoshi
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Patent number: 6989414Abstract: An aqueous emulsion having excellent water resistant property and comprising a copolymer obtainable by polymerizing ethylene and vinyl ester, and a nonionic polyoxyalkylene surface active agent, wherein the nonionic polyoxyalkylene surface active agent comprises 1 to 10 parts by weight of polyoxyalkylene alkyl ether and 0.01 part by weight or less of polyoxyalkylene phenyl ether based on 100 parts by weight of vinyl ester units in the copolymer is provided.Type: GrantFiled: March 14, 2002Date of Patent: January 24, 2006Assignee: Sumitomo Chemical Company, LimitedInventors: Tomoaki Sata, Tatsuo Mitsutake
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Patent number: 6878772Abstract: Fluoropolymer aqueous dispersions having particles with average diameters from 150 to 400 nm, comprising bifunctional fluorinated surfactants having formula: A-Rf—B??(I) wherein: A and B, equal to or different from each other, are: —(O)pCFX—COOM; M=NH4, alkaline metal, H; X=F, CF3; p is an integer equal to 0 or 1; Rf is a linear or branched perfluoroalkyl chain, or a (per)fluoropolyether chain such that the number average molecular weight of (I) is in the range 300-1,800.Type: GrantFiled: February 10, 2003Date of Patent: April 12, 2005Assignee: Solvay Solexis S.p.A.Inventors: Mario Visca, Alba Chittofrati, Valeri Kapeliouchko, Marco Malvasi
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Patent number: 6211259Abstract: The present invention includes new compositions for making polyurethane and polyurethane foam compositions. These compositions comprise the reaction product of an isocyanate A-Side and a B-Side comprising: (i) a polyol having a molecular weight of about 1000 g/mol or more, and having an average functionality of 2.0 or greater; (ii) a polyol having a Tg of about −80° C. or less, and having a molecular weight of about 1000 g/mol or more, and having an average functionality of 2.0 or greater; and(iii) a polyhydric alcohol having a molecular weight of about 90 g/mol or more, and having an average functionality of 3.0 or more. In the case of polyurethane foam compositions, the system also comprises water. The invention also includes processes for making the polyurethane and polyurethane foam compositions, as well as methods of adhering the same to cosmetic layers comprising thermoplastic, acrylic, and gel coat materials. The invention also includes articles made from these reinforced cosmetic layers.Type: GrantFiled: February 1, 1999Date of Patent: April 3, 2001Assignee: Aristech Acrylics LLCInventors: Keith A. Borden, Robert E. Anderson, Jr., Kathleen M. Yusko, Randall S. Reynolds
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Patent number: 6121372Abstract: An aqueous emulsion for use as a water- and oil-repellent agent, which aqueous emulsion is produced by copolymerizing least one of lower alkyl methacrylate, benzyl (meth)acrylate and vinylidene chloride with polyfluoroalkyl group-containing (meth)acrylate ester, dispersed in water and in the presence of a nonionic emulsifier containing .alpha.-[1-(allyloxy)methyl-2-(p-nonylphenoxy)ethyl]-.omega.-hydroxy(polyo xyethylene). The resulting aqueous emulsion is completely free from organic solvents and has a distinguishing freeze-thaw stability.Type: GrantFiled: February 8, 1999Date of Patent: September 19, 2000Assignee: Nippon Mektron LimitedInventors: Kazuhiro Yamamoto, Yuzuru Ishida
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Patent number: 6046271Abstract: An aqueous microemulsion polymerization procedure is described in which very small colloidal melt-processible fluoropolymer particles are produced from at least one monomer and optionally TFE. The polymerization procedure involves initiating polymerization by adding a free-radical initiator to a microemulsion of at least one liquid organic compound and at least one free-radical polymerizable monomer to the microemulsion.Type: GrantFiled: May 27, 1997Date of Patent: April 4, 2000Assignee: W. L. Gore & Associates, Inc.Inventors: Huey Shen Wu, Jack Hegenbarth, Xin Kang Chen, Jian Guo Chen
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Patent number: 5959026Abstract: Microemulsions are described which comprise:(a) water;(b) a fluoropolyoxyalkylene having hydrogenated end groups and/or hydrogenated repetitive units;(c) an hydrocarbon C.sub.1 -C.sub.20, preferably C.sub.1 -C.sub.12, of aliphatic, aromatic, or mixed type, optionally containing halogens, preferably chlorine and/or bromine;(d) a fluorinated surfactant.Such microemulsions can be used in radical (co)polymerization processes in aqueous emulsion of one or more fluorinated olefinic monomers, optionally in association with one or more non fluorinated olefins.Type: GrantFiled: October 2, 1997Date of Patent: September 28, 1999Assignee: Ausimont S.p.A.Inventors: Julio A. Abusleme, Alba Chittofrati
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Patent number: 5919851Abstract: A paint composition comprising, as a leveling agent, 0.01 to 3.0 parts by weight of a polyfluorinated carbon chain-containing compound and 0.01 to 3.0 parts by weight of a silicone oil per 100 parts by weight of a film forming component and being capable of forming a film being excellent in water- and oil-repelling property and stain resistance, and painted articles being excellent in water- and oil-repelling property and stain resistance can be provided.Type: GrantFiled: April 8, 1997Date of Patent: July 6, 1999Assignee: Daikin Industries, Ltd.Inventors: Seitaro Yamaguchi, Koichiro Ogita, Nobuyuki Tomihashi
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Patent number: 5830991Abstract: The invention provides an economical and efficient process for preparing a dimeric cyclic ester of an .alpha.-hydroxycarboxylic acid by depolymerizing a corresponding .alpha.-hydroxycarboxylic acid oligomer, which comprises the steps of (1) heating a mixture containing the .alpha.-hydroxycarboxylic acid oligomer and at least one high-boiling polar organic solvent having a boiling point within a range of 230.degree.-450.degree. C. to a temperature, at which the depolymerization of the oligomer takes place, under atmospheric pressure or reduced pressure, (2) dissolving the oligomer in the solvent until a residual rate of a melt phase of the oligomer reaches 0.5 or lower, (3) further continuing the heating at the temperature, at which the depolymerization of the oligomer takes place, to depolymerize the oligomer, (4) distilling out the dimeric cyclic ester formed together with the high-boiling polar organic solvent, and (5) recovering the dimeric cyclic ester from the distillate.Type: GrantFiled: January 23, 1997Date of Patent: November 3, 1998Assignee: Kureha Kagaku Kagyo KKInventors: Zenya Shiiki, Yukichika Kawakami
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Patent number: 5648435Abstract: A process of preparing multicyanate esters by: a) reacting an adduct of a tertiary amine and a phenol-formaldehyde oligomer or derivative thereof with cyanogen halide in a solvent reaction medium under conditions to form a reaction product stream containing at least one of the following compounds selected from the group consisting of tertiary amine-hydrohalide salt, solvent, and impurities, and, based upon the total weight of the reaction product stream excluding the weight of said tertiary amine-hydrohalide salt, from about 10 percent to about 40 percent of a multicyanate ester; b) recycling a portion of said reaction product stream into the mixture of step a; and c) separating and recovering said solvent and tertiary amine from said reaction product stream. The multicyanate ester products produced are useful as bonding agents in friction materials, molding materials, coatings, and adhesives.Type: GrantFiled: November 17, 1995Date of Patent: July 15, 1997Assignee: AlliedSignal Inc.Inventors: David W. H. Roth, Jr., Sajal Das
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Patent number: 5639820Abstract: A method for preparing an aqueous dispersion composition containing a fluorocopolymer by the emulsion polymerizing of a polymerizable compound containing a polyfluoroalkyl group and another copolymerizable compound noncompatible with the polymerizable compound in an aqueous solution containing a compatibilizer, wherein the compatibilizer is selected from the group consisting of (a) a low-molecular weight compound having a perfluoroalkyl group and a hydrocarbon alkyl group in a molecule, (b) a low-molecular weight compound having a perfluoropolyether group and a hydrocarbon alkyl group in a molecule, (c) a macromolecular compound prepared by the copolymerization of a polymerizable compound containing a perfluoroalkyl group and a polymerizable hydrocarbon compound, and (d) a hydrocarbon macromolecular compound having a perfluoropolyether group in a molecule does not cause coagulation and can give an aqueous dispersion composition having the improved compatibility between the polymerizable monomers.Type: GrantFiled: June 2, 1995Date of Patent: June 17, 1997Assignee: Daikin Industries, Ltd.Inventors: Motonobu Kubo, Masamichi Morita
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Patent number: 5629367Abstract: A method of making pigment concentrate particles having pigment uniformly dispersed in a polymer and exhibiting a controlled morphology and narrow particle size distribution. The method involves dispersing pigment particles in a pigment dispersant liquid to form a first dispersion phase; blending the first dispersion phase with a binder to produce a second dispersion phase; mixing the second dispersion phase under sufficient shear to produce a suspension of small dispersion phase droplets in an immiscible suspending liquid; allowing the small dispersion phase droplets in the suspension to coalesce to a larger size at which substantially no further coalescence can occur; mixing the suspension of coalesced droplets with an extracting liquid to remove the pigment dispersant liquid from the coalesced droplets; and isolating the resulting pigment concentrate particles.Type: GrantFiled: January 31, 1995Date of Patent: May 13, 1997Assignee: Eastman Kodak CompanyInventors: Kevin D. Lofftus, Alexandra D. Bermel
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Patent number: 5530053Abstract: Electrostatic toners comprising polymeric dyes comprising of (1) discrete segments that are dispersible in highly fluorinated solvents and (2) discrete color-imparting segments. These toners can be prepared by a means of a polymerization process, wherein macromers containing highly fluorinated dispersible segments are grafted onto a polymer having chromophores attached thereto.Type: GrantFiled: May 24, 1995Date of Patent: June 25, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventors: S. Prabhakara Rao, Terrance P. Smith
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Patent number: 5483013Abstract: The present invention is directed to a process of preparing multicyanate esters by: a) reacting an adduct of a tertiary amine and a phenol-formaldehyde oligomer or derivative thereof with cyanogen halide in a solvent reaction medium under conditions to form a reaction product stream containing at least one of the following compounds selected from the group consisting of tertiary amine-hydrohalide salt, solvent, and impurities, and, based upon the total weight of the reaction product stream excluding the weight of said tertiary amine-hydrohalide salt, from about 10 percent to about 40 percent of a multicyanate ester; b) recycling a portion of said reaction product stream into the mixture of step a; and c) separating and recovering said solvent and tertiary amine from said reaction product stream.The multicyanate ester products produced according to the present invention are useful as bonding agents in friction materials, molding materials, coatings, and adhesives.Type: GrantFiled: January 27, 1995Date of Patent: January 9, 1996Assignee: AlliedSignal Inc.Inventors: David W. H. Roth, Jr., Sajal Das
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Patent number: 5438093Abstract: Solution and RIM polymerization of cycloolefins containing at least one norbornene moiety is carried out in the presence of a methathesis catalyst system and an activator, particularly a chlorosilane activator, to obtain faster reaction with higher conversions at lower mold temperatures. The methathesis catalyst system includes an organoammonium molybdate or tungstate catalyst and an alkylaluminum or an alkylaluminum halide cocatalyst. The chlorosilane activator is used at a level of 0.05 to 10 millimoles per mole of the cycloolefin monomers. The polymers of cycloolefins can be impact modified and/or flame-retarded.Type: GrantFiled: June 26, 1992Date of Patent: August 1, 1995Assignee: B. F. Goodrich CompanyInventors: Paul T. Stricharczuk, Robert J. Minchak, Timothy J. Kettering, Dennis J. Janda, Glen R. Gribble, Jr.
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Patent number: 5424122Abstract: The invention relates to a neutral nonionic latex comprising:(a) about 5 to about 70 weight percent of a nonionic polymer comprising polymerized free-radically polymerizable nonionic monomer, based upon the total weight of the neutral nonionic latex, wherein the free radically polymerizable nonionic monomer comprises:(i) about 90 to about 99 percent by weight of nonionic alkyl acrylate monomer; and(ii) about 1 to about 10 percent by weight of nonionic amide monomer; wherein the weight percentages of (i) and (ii) are based upon the total weight of (i) plus (ii);(b) about 30 to about 95 weight percent of an aqueous phase, based upon the total weight of the neutral nonionic latex; and(c) about 2 to about 10 weight percent of a nonionic emulsifier based upon the total weight of the nonionic polymer plus the nonionic emulsifier;wherein particles of the nonionic polymer are stabilized by the nonionic emulsifier and dispersed within the aqueous phase.Type: GrantFiled: December 9, 1991Date of Patent: June 13, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventors: Michael D. Crandall, Robert L. Nelson
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Patent number: 5180755Abstract: A method for producing antistatic polyurethane resins according to the present invention comprises a reaction of a compound having at least two active hydrogen atoms with an organic isocyanate in the presence of at least one kind of complex compounds represented by a general formula [Me(ClO.sub.4).sub.n ].sub.x [R(OH).sub.y ].sub.z and being liquid at room temperature, wherein Me is an element belonging to Group I or II in the periodic table; n is a number of 1-2; x is a number of 1-5; y is a number of 1-3; z is a number of 1-6; and R is a residual group other than hydroxyl group in a polyhydric alcohol or its derivative. Me of said complex compounds is preferably Li, Na, K, Ca or Ba.As antistatic agents are liquid at room temperature in the present invention, they can be formulated uniformly within raw materials of polyurethane resins. By virtue thereof, the antistatic effect is exhibited homogeneously and so highly.Type: GrantFiled: June 26, 1991Date of Patent: January 19, 1993Assignee: Bridgestone CorporationInventors: Kuniaki Yasunaga, Shigeru Ueno
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Patent number: 4835084Abstract: Suspension stabilizer particles are removed from the surface of polymer particles formed in a limiting coalescence formation technique by dissolving in a solution containing a fluoralkyl polyether surface active agent.Type: GrantFiled: March 21, 1988Date of Patent: May 30, 1989Assignee: Eastman Kodak CompanyInventors: Mridula Nair, Zona R. Pierce
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Patent number: 4826905Abstract: A silicone rubber composition composed of a high-molecular diorganopolysiloxane, a reinforcing silica filler and an organic peroxide as a curing agent is further compounded with a fluorine-containing low-polymeric compound such as poly(chlorotrifluoroethylene) and perfluorinated polyether compound of the formula F--[--CF(CF.sub.3)--CF.sub.2 --O--].sub.v --O--CF.sub.2 --CF.sub.3, in which v is 2 to 100, as well as fluoroalkyl-substituted organopolysiloxanes. The silicone rubber composition can give a cured silicone rubber product having greatly improved resistance against dynamic fatigue as in repeated cycles of stretching and relaxation.Type: GrantFiled: December 11, 1987Date of Patent: May 2, 1989Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Kunio Itoh, Kiyoshi Imai, Takeshi Fukuda
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Patent number: 4788106Abstract: A curable composition comprising (A) a siloxane-polyester copolymer, (B) one or more solvents for the siloxane-polyester copolymer, (C) a silane having silicon-bonded alkoxy or alkoxy-alkoxy groups and a silicon-bonded substituent containing an epoxy group, (D) aluminium acetylacetonate and (E) a tetraalkyl titanate.The compositions are heat-curable and are useful for the formation of protective and decorative coatings on substrates such as metals and plastics.Type: GrantFiled: February 8, 1988Date of Patent: November 29, 1988Assignee: Dow Corning, Ltd.Inventor: Anthony G. Short
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Patent number: 4746682Abstract: A liquid composition is provided suitable for use as a flame retardant additive for polyurethane foams. The composition overcomes the problems of high viscosity and precipitates forming in formulations of phosphate esters and polybromodiphenyl oxides and avoids scorch and smoldering while preparing polyurethane foams meeting the California 117 standard. In addition, the composition provides an unexpected advantage of improved efficacy and heat stability. The process for preparing the flame retarded polyurethane foam and the foam itself are also claimed.Type: GrantFiled: April 1, 1987Date of Patent: May 24, 1988Assignee: FMC CorporationInventor: Joseph Green
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Patent number: 4621104Abstract: Liquid bromine-containing alkoxylation products of butyne-(1,4)-diol which are storage stable are produced. More specifically, 1.5 to 2.5 mols alkylene oxide are reacted with each mol of butyne-(1,4)-diol present at elevated temperature in the presence of a catalyst. The catalyst is selected from (1) thioethers having a molecular weight of up to 5000 obtained by adding a mercaptan and/or mercaptoalcohol to an unsaturated hydrocarbon and/or (2) thioethers other than those of (1) having a molecular weight of from 500 to 5000 and/or (3) alkali metal chlorides. This alkoxylation product is then reacted with bromine at -10.degree. to 80.degree. C. The bromide is reoxidized with aqueous hydrogen peroxide solution, stabilized with a relatively non-volatile epoxide and dehydrated. The product thus obtained is particularly useful in the production of flame resistant isocyanate addition products such as polyurethane foams.Type: GrantFiled: October 9, 1985Date of Patent: November 4, 1986Assignee: Bayer AktiengesellschaftInventors: Manfred Dietrich, Manfred Schmidt, Rolf Wiedermann, Klaus Konig
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Patent number: 4607077Abstract: Poly(dicyclopentadiene) made with an olefin metathesis catalyst system by a Reaction Injection Molding process is improved by adding flame retardant compounds.Type: GrantFiled: May 7, 1985Date of Patent: August 19, 1986Assignee: Hercules IncorporatedInventors: Paul A. Silver, Alexander Lukacs, III
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Patent number: 4585829Abstract: A method of imparting internal mold release properties to reaction injection molding polyurethane compositions by the addition of a perfluoroalkylorganocarboxylic acid or a salt thereof. This invention also relates to the production of novel perfluoroalkylorganodibutyltindioxide compounds which are inherently catalytic and can also impart the property of internal mold releasability to RIM compositions.Type: GrantFiled: May 29, 1984Date of Patent: April 29, 1986Assignee: Union Carbide CorporationInventors: An-Li Kuo, Errol D. Goddard, James S. Ritscher
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Patent number: 4564661Abstract: An improvement is disclosed in a process for conducting PTFE dispersion polymerization, comprising use of tertiary perfluoroalkoxy compounds as surfactants.Type: GrantFiled: March 12, 1985Date of Patent: January 14, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventor: Aleksander Beresniewicz
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Patent number: 4546129Abstract: New compositions of matter are disclosed which are allylated di and polycyclopentadiene diphenols. These new compositions are useful in thermoset resin compositions comprising styrene, a dicyclopentadiene-modified unsaturated polyesteramide and said allylated di and polycyclopentadiene diphenol(s).Type: GrantFiled: June 18, 1984Date of Patent: October 8, 1985Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.