From Fluorine-containing Reactant Patents (Class 528/401)
  • Patent number: 11905483
    Abstract: A tribological system, comprising a main body and a sandwich lubrication, in which the sandwich lubrication includes a binder-free solid lubricant layer comprising a solid lubricant, and a lubricant layer comprising a lubricant. The binder-free solid lubricant layer and the lubricant layer are present as separate layers on the main body and wherein the mass ratio of solid lubricant to lubricant is at most 0.05:1.
    Type: Grant
    Filed: November 5, 2020
    Date of Patent: February 20, 2024
    Assignee: KLUEBER LUBRICATION MUENCHEN SE & CO. KG
    Inventors: Martin Schweigkofler, Balasubramaniam Vengudusamy, Stefan Seemeyer, Dirk Loderer
  • Patent number: 10053538
    Abstract: A process for preparing a low-molecular weight fluoropolyether containing an acid fluoride by decomposing a triflate or trifluoroacetate of a fluoropolyether having a hydroxyl group in the presence of a Lewis acid.
    Type: Grant
    Filed: July 28, 2015
    Date of Patent: August 21, 2018
    Assignee: MORESCO CORPORATION
    Inventor: Tsuyoshi Shimizu
  • Patent number: 9796811
    Abstract: A polymer compound comprising a structural unit represented by the formula (1): wherein Ring A and Ring B represent each independently a heterocyclic ring, and the heterocyclic ring may have a substituent, Ring C represents an aromatic hydrocarbon ring obtained by condensing two or more benzene rings, the aromatic hydrocarbon ring has at least one of an alkyl group, an alkoxy group, an alkylthio group, an amino group or a hydroxyl group, and these groups may have a substituent, Z1 and Z2 represent each independently a group represented by the formula (Z-1), a group represented by the formula (Z-2), a group represented by the formula (Z-3), a group represented by the formula (Z-4) or a group represented by the formula (Z-5), wherein R represents an alkyl group, an alkoxy group, an alkylthio group, an aryl group or a mono-valent heterocyclic group, and these groups may have a substituent, and when there exist a plurality of R, these may be the same or different.
    Type: Grant
    Filed: August 21, 2014
    Date of Patent: October 24, 2017
    Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Tomoya Kashiki, Hiroki Terai
  • Patent number: 9309388
    Abstract: Objects of the present invention are to provide a rubber composition that can obtain a rubber elastic body having small rolling resistance and excellent impact resilience and a method for producing the same, and to provide a tire having small rolling resistance and excellent impact resilience. The rubber composition of the present invention is obtained by kneading a rubber component containing 30 to 95% by mass of a conjugated diene polymer (A) and 5 to 70% by mass of cross-linked rubber particles (B) with 20 to 100 parts by mass of silica (C) based on 100 parts by mass of the rubber component.
    Type: Grant
    Filed: February 14, 2012
    Date of Patent: April 12, 2016
    Assignee: JSR CORPORATION
    Inventors: Koji Okada, Ryoji Tanaka
  • Patent number: 9159928
    Abstract: Disclosed are an amine-oxide-group-containing conjugated polymer photoelectric material and application thereof. The amine-oxide-group-containing conjugated polymer photoelectric material consists of conjugated main chains and a side chain containing an amine oxide unit, and is applied in an organic photoelectric device. The material has desirable alcohol/water solubility and photoelectric properties, is suitable for making a multi-layer solution for machining a device, and meanwhile can prevent an adverse effect incurred by freely moving counter ions in a common polyelectrolyte to the device. The material may be used as a cathode interface modification layer applied in organic photoelectric devices such as light-emitting and photovoltaic devices, so as to improve performance of the devices.
    Type: Grant
    Filed: December 12, 2012
    Date of Patent: October 13, 2015
    Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY
    Inventors: Fei Huang, Xing Guan, Kai Zhang, Yong Cao
  • Patent number: 9093265
    Abstract: One embodiment is a method for semiconductor processing. In this method, a precursor film is provided over a semiconductor substrate, where the precursor film is made of a structural former and porogen. Prior to cross-linking, the porogen is removed by exposure to UV radiation having one or more wavelengths in the range of 150 nm to 300 nm, while a temperature of 300° C. to 500° C. is applied to the semiconductor substrate. Meanwhile, a Argon:Helium flow rate of 80>Ar>10 slm, 80>He>10 slm is set for the ambient substrate environment where the ratio of Ar:He ranges from 0:1 to 1:0 by volume or molality.
    Type: Grant
    Filed: October 15, 2013
    Date of Patent: July 28, 2015
    Assignee: Taiwan Semiconductor Manufacturing Co., Ltd.
    Inventors: Po-Cheng Shih, Hui-Chun Yang, Chung-Chi Ko, Kuang-Yuan Hsu
  • Patent number: 9062160
    Abstract: One catalyst-free method of forming a polyurethane comprises forming a first emulsion comprising a first monomer, a surfactant, a water immiscible organic solvent, and water. The first monomer comprises two or more pentafluorophenyl carbonate groups. The first emulsion is combined with an aqueous mixture containing a second monomer comprising two or more nucleophilic amine groups, thereby forming a second emulsion. The first and second monomers of the second emulsion are allowed to react by interfacial polymerization, thereby forming a polyurethane. The polyurethane can have a number average molecular weight (Mn) of about 30000 to about 80000. The method is compatible with introducing pendant functionality into the polyurethane by way of cyclic carbonate precursors to the first monomer.
    Type: Grant
    Filed: January 23, 2014
    Date of Patent: June 23, 2015
    Assignees: International Business Machines Corporation, Agency For Science, Technology And Research
    Inventors: Julian M. W. Chan, Daniel J. Coady, Amanda C. Engler, Jeannette M. Garcia, James L. Hedrick, Zhan Yuin Ong, Haritz Sardon, Yi Yan Yang
  • Patent number: 9023977
    Abstract: A method of making a fluoropolyether elastomer containing triazine groups and having a glass transition temperature of less than ?40° C.
    Type: Grant
    Filed: October 5, 2010
    Date of Patent: May 5, 2015
    Assignee: 3M Innovative Properties Company
    Inventors: Steven G. Corveleyn, Rudolf J. Dams, Werner M. A. Grootaert, Gregg D. Dahlke, Miguel A. Guerra
  • Patent number: 9018270
    Abstract: A method of forming a polymer is provided, the method comprising: Providing a first monomer comprising one or more aromatic moieties, the first monomer comprising at least two amino groups, each of the amino groups being attached to an aromatic moiety; and contacting said first monomer with formaldehyde or a source of methylene. Polymers made by such a method and uses of such polymers are also described.
    Type: Grant
    Filed: September 12, 2011
    Date of Patent: April 28, 2015
    Assignee: University College Cardiff Consultants Limited
    Inventors: Neil Bruce McKeown, Mariolino Carta, Matthew James Croad
  • Patent number: 8969510
    Abstract: Fluorinated supramolecular polymers containing at least 5% by weight of covalently bonded fluorine atoms, based on total weight of the polymers are disclosed. The polymers comprise a fluorinated polymer chain and a (self-)complementary unit capable of forming at least three hydrogen bonds being covalently bonded to the fluorinated polymer chain. Also disclosed are materials comprising (a) a fluorinated supramolecular polymer and (b) a non-fluorinated polymer and/or (c) a fluorinated compound, the non-fluorinated polymer being a polymer containing less than 5% by weight of covalently bonded fluorine atoms, based on the total weight of the non-fluorinated polymer, and the fluorinated compound being either a low molecular weight fluorinated compound comprising at least one fluorine atom and having a molecular weight of 34 to 600 amu, or a fluoropolymer containing at least 5% by weight of covalently bonded fluorine atoms and a Mn from about 600 to about 5000.
    Type: Grant
    Filed: November 22, 2011
    Date of Patent: March 3, 2015
    Assignee: SupraPolix B.V.
    Inventor: Anton Willem Bosman
  • Patent number: 8927684
    Abstract: Compounds of Formula (I): (formula (I)) where: X1 and X2 are the same or different and each is independently Cl, Br, I, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; and, Y is O, S, Se, NR1, R1C—CR2 or R1C?CR2, wherein R1 and R2 are the same or different and are each independently H or an organic group, are useful as monomers to produce oligomers or polymers that are useful in organic electronic devices.
    Type: Grant
    Filed: November 3, 2010
    Date of Patent: January 6, 2015
    Assignee: National Research Council of Canada
    Inventors: Zhao Li, Jianfu Ding, Jianping Lu, Ye Tao
  • Patent number: 8907046
    Abstract: Copolymers containing at least one perfluoropolyether segment and multiple aminooxalylamino groups are described. Methods of making the copolymers are also described. The copolymers can be prepared by reacting an oxalylamino-containing compound and an amine compound having at least two primary amino groups, at least two secondary amino groups, or at least one primary amino group plus at least one secondary amino group.
    Type: Grant
    Filed: December 22, 2010
    Date of Patent: December 9, 2014
    Assignee: 3M Innovative Properties Company
    Inventors: Suresh S. Iyer, Miguel A. Guerra, Richard G. Hansen, David S. Hays, Ramesh C. Kumar, George G. I. Moore, Yu Yang
  • Patent number: 8889230
    Abstract: A fluorochemical derived from monomers with a side chain, wherein the side chain includes a perfluoroalkyl group with 1-6 carbon atoms and a hydrocarbon spacer group attached to the perfluoroalkyl group, wherein the spacer group has 15-50 carbon atoms. The perfluoroalkyl group is non-crystallizable at room temperature and the spacer group is crystallizable at room temperature.
    Type: Grant
    Filed: August 17, 2007
    Date of Patent: November 18, 2014
    Assignee: 3M Innovative Properties Company
    Inventors: Richard M. Flynn, Michael A. Yandrasits
  • Patent number: 8865944
    Abstract: A process for purifying a polyol (per)fluoropolyether derivative [polyol (P)] from a mixture of hydroxyl (per)fluoropolyether derivatives [mixture (M)]. Such polyol (P) comprising one or more hydroxyl (per)fluoropolyether derivatives [PFPE (OH)] comprising at least one (per)fluoropolyoxyalkylene chain (chain Rf) and at least one end-group having formula (t3) —CF2CH2OCH2CH(OH)CH2OCH2CH(OH)CH2OH. Such mixture (M) comprising the polyol (P) and at least one PFPE (OH) different from the polyol (P) and comprising at least one chain Rf and at least one end-group selected from end-groups having formula (t1) —CF2CH2OH and formula (t2) —CF2CH2OCH2CH(OH)CH2OH.
    Type: Grant
    Filed: May 6, 2010
    Date of Patent: October 21, 2014
    Assignee: Solvay Specialty Polymers Italy S.p.A.
    Inventors: Graziano Giuseppe Vezzulli, Piero Gavezotti, Fabrizio Mutta, Claudio Adolfo Pietro Tonelli
  • Patent number: 8865843
    Abstract: The present disclosure is directed to a sag control agent comprising a reaction product of an isocyanate and a fluorinated amine. This disclosure is further directed to a coating composition comprising the sag control agent. This disclosure is also directed to a process of forming a sag-free coating layer on a substrate.
    Type: Grant
    Filed: September 16, 2010
    Date of Patent: October 21, 2014
    Assignee: Axalta Coating Systems IP Co., LLC
    Inventors: Rajesh Gopalan Saliya, Ayumu Yokoyama, Sheau-Hwa Ma, Axel Hans-Joachim Herzog
  • Publication number: 20140302267
    Abstract: A monolithic, self-stratifying polymer coating, comprising: inner and outer-most surfaces on opposite sides of the coating, the inner surface being in contact with and adhered to an article; a surface region, extending from the outermost surface to a depth of about 2 nm from the outermost surface; a middle region, extending from a depth of about 2 nm from the outermost surface to a depth of less than about 2000 nm from the outermost surface; and a bulk region, extending from a depth of less than about 2000 nm from the outermost surface to the inner surface; wherein the surface region comprises a fluorous polyoxetane having the formula: (I) wherein n is an integer of 0-1 1, and m is an integer>0, in a greater concentration relative to the middle and bulk regions; wherein the middle region comprises 3F-SiO1.5 groups in a greater concentration relative to the surface and bulk regions; and wherein the bulk region comprises a polyurethane in a greater concentration relative to the surface and middle regions.
    Type: Application
    Filed: July 26, 2012
    Publication date: October 9, 2014
    Applicant: VIRGINIA COMMONWEALTH UNIVERSITY
    Inventors: Kenneth J. Wynne, Wei Zhang, Chenyu Wang, Souvik Chakrabarty
  • Patent number: 8841411
    Abstract: The present invention relates to polymers comprising repeating unit(s) of the formula (I), and their use in electronic devices. The polymers according to the invention have excellent solubility in organic solvents and excellent film-forming properties. In addition, high charge carrier mobilities and high temperature stability of the emission color are observed, if the polymers according to the invention are used in polymer light emitting diodes (PLEDs).
    Type: Grant
    Filed: June 10, 2009
    Date of Patent: September 23, 2014
    Assignee: BASF SE
    Inventors: Shin-Ichiro Kawano, Martin Baumgarten, Klaus Müllen, Peter Murer, Thomas Schäfer, Moussa Saleh
  • Patent number: 8822633
    Abstract: Luminescent polymers having sterically twisted arylene repeat units are provided, which are particularly suited as electroluminescent polymers. Monomers necessary for the synthesis of the sterically twisted polyarylene are provided, as are electroluminescent device utilizing these polymers.
    Type: Grant
    Filed: February 22, 2006
    Date of Patent: September 2, 2014
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Matthew L. Marrocco, Virgil J. Lee, Farshad J. Motamedi
  • Patent number: 8785556
    Abstract: 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 fluorinated component and an adhesion promoter compound. The adhesion promoter compound can include an alkoxy group, a furfuryl-containing ring structure, and a reactive group.
    Type: Grant
    Filed: April 30, 2012
    Date of Patent: July 22, 2014
    Assignee: Cytonix, LLC
    Inventor: James F. Brown
  • Patent number: 8772420
    Abstract: A fluorinated polyester blend is prepared by melt blending a fluorovinyl ether functionalized polyester with a non-fluorinated polyester. The fluoroether functionalized polyester can be a homopolymer or a copolymer. The blend is useful for preparing fibers, yarns, fabrics, garments, carpets, and other shaped articles. The shaped articles exhibit durable soil, oil, and water repellency.
    Type: Grant
    Filed: December 28, 2011
    Date of Patent: July 8, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Neville Everton Drysdale, Fredrik Nederberg
  • Patent number: 8669336
    Abstract: The invention relates to a coating composition comprising short chain fluorinated acrylates and to the use of short chain fluorinated acrylates as levelling agents for pigmented and unpigmented coating compositions. The coating composition comprises a) a film forming binder resin, and b) a copolymer made by controlled polymerization or by conventional radical polymerization comprising a monomer (M1x) selected from unsaturated monomers out of the group of (meth)acrylates, styrenic monomers or (meth)acrylamides whereby the copolymer contains at least >30 wt % (meth)acrylates; and a monomer (M2y) selected from C1-C4-fluoralkyl(meth)acrylates; x denotes the total number of monomers M1 within the structural element (M1x): x>5, preferred, 10-1000, most preferred, 10-500; y denotes the total number of monomers M2 within the structural element (M2y): y>1, preferred, 2-20, most preferred 2-10; c) optional other conventional coating components and/or additives.
    Type: Grant
    Filed: February 3, 2009
    Date of Patent: March 11, 2014
    Assignee: BASF SE
    Inventors: Andreas Möck, Ralf Knischka, Clemens Auschra
  • Patent number: 8664353
    Abstract: A process for purifying a polyol(per)fluoropolyether derivative [polyol (P)] from a mixture (M) of hydroxyl(per)fluoropolyether derivatives, such polyol (P) comprising one or more hydroxyl(per)fluoropolyether derivatives [PFPEs (OH)] comprising at least one (per)fluoropolyoxyalkylene chain (chain Rf) and at least one end-group having formula (t3): —CF2CH2OCH2CH(OH)CH2OCH2CH(OH)CH2OH, such mixture (M) comprising said polyol (P) and at least one hydroxyl(per)fluoropolyether derivative [PFPE (OH)] different from polyol (P) and comprising at least one chain Rf and at least one end-group selected from end-groups having formula (t1): —CF2CH2OH and formula (t2): —CF2CH2OCH2CH(OH)CH2OH.
    Type: Grant
    Filed: May 6, 2010
    Date of Patent: March 4, 2014
    Assignee: Solvay Solexis S.P.A.
    Inventors: Claudio Adolfo Pietro Tonelli, Graziano Giuseppe Vezzulli, Rosaldo Picozzi, Piero Gavezotti
  • Patent number: 8629212
    Abstract: Compositions of PHAs with PBS and/or PBSA are described and methods of making the same.
    Type: Grant
    Filed: August 5, 2013
    Date of Patent: January 14, 2014
    Assignee: Metabolix, Inc.
    Inventors: Rajendra K. Krishnaswamy, Xiudong Sun
  • Patent number: 8602523
    Abstract: Disclosed is an ink jet printhead comprising a plurality of channels, wherein the channels are capable of being filled with ink from an ink supply and wherein the channels terminate in nozzles on one surface of the printhead, the surface being coated with a coating composition comprising a fluorinated poly(amide-imide) copolymer.
    Type: Grant
    Filed: November 11, 2011
    Date of Patent: December 10, 2013
    Assignee: Xerox Corporation
    Inventors: Edward F Grabowski, Yuhua Tong
  • Patent number: 8575300
    Abstract: Disclosed herein is a telechelic diacrylate fluoropolymer and a process for manufacture of the fluoropolymer. The diacrylate copolymer is of formula CH2?CR?COO—(CH2)n—R—(CH2)n—OOCCR??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.
    Type: Grant
    Filed: November 14, 2012
    Date of Patent: November 5, 2013
    Assignees: E I du Pont de Nemours and Company, Le Centre National de la Recherche Scien
    Inventors: Ming-Hong Hung, Bruno Ameduri, Georgi Kostov
  • Patent number: 8557952
    Abstract: The invention pertains to novel (per)fluoropolyethers comprising at least one (per)fluoropolyoxyalkylene chain (chain Rf) comprising at least one recurring unit (R2) having formula: CF2—CF(CF2OSO2F)—O— (poly(fluorosulfate) PFPE) to a process for their manufacture, and to their use for providing functional (per)fluoropolyethers.
    Type: Grant
    Filed: December 2, 2009
    Date of Patent: October 15, 2013
    Assignee: Solvay Solexis S.p.A.
    Inventors: Giuseppe Marchionni, Silvia Petricci, Pier Antonio Guarda
  • Publication number: 20130267616
    Abstract: A method of forming a polymer is provided, the method comprising: Providing a first monomer comprising one or more aromatic moieties, the first monomer comprising at least two amino groups, each of the amino groups being attached to an aromatic moiety; and contacting said first monomer with formaldehyde or a source of methylene. Polymers made by such a method and uses of such polymers are also described.
    Type: Application
    Filed: September 12, 2011
    Publication date: October 10, 2013
    Applicant: University College Cardiff Consultants Limited
    Inventors: Neil Bruce McKeown, Mariolino Carta, Matthew James Croad
  • Patent number: 8536299
    Abstract: Rigid-rod copolymer compositions incorporating PBO (poly(p-phenylenebenzobisoxazole)), DiOH-PBO (poly(2,5-dihydroxy-1,4-phenylenebenzobisoxazole), DiOH-PBI (poly(2,5-dihydroxy-1,4-phenylenebenzobisimidazole)), DiOH-PyBI (poly(2,5-dihydroxy-1,4-phenylenepyridobisimidazole), PBZT (poly(p-phenylenebenzobisthiazole)) and its corresponding dihydroxy analogues attached to a flexibilizing hexafluoroisopropylidene linkage are described. Also described are their fabrication into fibers by a dry jet wet spinning technique and the measured fiber mechanical properties. The copolymer compositions are highly flame-resistant and have potential utility for fire-protective clothing.
    Type: Grant
    Filed: December 8, 2008
    Date of Patent: September 17, 2013
    Assignee: University of Dayton
    Inventors: Thuy D. Dang, Zongwu Bai, Narayanan Venkat, Alexander B. Morgan
  • Patent number: 8519094
    Abstract: Process for heating a polymer-containing stream being transferred from a polymerization reactor to a separation zone or device, by passing the stream through at least two heaters operating in parallel, each heater having at least one transfer line for the stream and a heater for heating the transfer line. The average particle of the polymer is below 3 mm, the temperature of the polymer-containing stream at the outlet of all heaters is maintained above the dew point of the stream, and no heater has a volumetric flowrate of polymer-containing stream more than three times that of any other heater.
    Type: Grant
    Filed: April 15, 2009
    Date of Patent: August 27, 2013
    Assignee: Ineos Manufacturing Belgium NV
    Inventors: Daniel Marissal, Marc Parisel, Brent Walworth
  • Patent number: 8507642
    Abstract: The invention pertains to a process for the addition of at least one (per)fluoropolyether peroxide comprising at least one peroxidic moiety and at least one fluoropolyoxyalkene chain (chain Rf) (i.e. a fluorocarbon segment comprising ether linkages in main chain) [peroxide (P)] onto a per(halo)fluorinated aromatic compound [compound (F)], so as to yield an addition compound of said compound (F), said addition compound [compound (A)] comprising at least one perfluorinated non-aromatic cyclic moiety having at least two substituents comprising a chain Rf and, optionally, conjugated or non conjugated double bond(s). Said addition compounds have been notably found useful as additives for (per)fluorinated fluids and lubricants or as base materials for the manufacture of gum and/or graft polymer compositions.
    Type: Grant
    Filed: March 13, 2009
    Date of Patent: August 13, 2013
    Assignee: Solvay Solexis S.p.A.
    Inventors: Giuseppe Marchionni, Marco Avataneo, Pier Antonio Guarda
  • Publication number: 20130193382
    Abstract: The present invention relates to compounds of the formula (I) and to the use thereof in electronic devices. The invention furthermore relates to electronic devices, preferably organic electroluminescent devices (OLEDs), comprising one or more com-pounds of the formula (I). The invention again furthermore relates to the preparation of compounds of the formula (I) and to formulations comprising one or more compounds of the formula (I).
    Type: Application
    Filed: September 6, 2011
    Publication date: August 1, 2013
    Applicant: MERCK PATENT GmbH
    Inventors: Arne Buesing, Thomas Eberle, Irina Martynova, Teresa Mujica-Fernaud
  • Patent number: 8487050
    Abstract: A composition comprises a fluorine-containing aromatic polymer, an epoxy compound and an initiator. Its use as film, laminate with polyimide or copper foils, copper-clad laminated board and adhesive film. The fluorine-containing aromatic polymer is preferably a fluorine-containing aryl ether polymer. The initiator is preferably a cationic initiator.
    Type: Grant
    Filed: April 27, 2006
    Date of Patent: July 16, 2013
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Kazushi Omote, Ai Nishichi, Shimpei Sato
  • Patent number: 8481607
    Abstract: A surface treatment method for a fluororesin molded body, which is a method for treating a surface of an ETFE molded body by using a glow discharge generated by a pulsed electric field having a voltage-rising time of at most 10 ?sec in a nitrogen atmosphere under a pressure in the vicinity of atmospheric pressure; which comprises carrying out a plurality of glow discharge treatments at intervals of at least 0.01 sec so that the discharge density of each of the glow discharges is from 40 to 200 W·min/m2, and that the total discharge density of the glow discharges is from 220 to 800 W·min/m2. Further, an ETFE molded body subjected to a surface treatment by the surface treatment method.
    Type: Grant
    Filed: July 26, 2012
    Date of Patent: July 9, 2013
    Assignee: Asahi Glass Company, Limited
    Inventors: Hiroshi Aruga, Koichi Oda
  • Patent number: 8455612
    Abstract: A one pot method of preparing cyclic carbonyl compounds comprising an active pendant pentafluorophenyl ester group is disclosed. The cyclic carbonyl compounds can be polymerized by ring opening methods to form ROP polymers comprising repeat units comprising a side chain pentafluorophenyl ester group. Using a suitable nucleophile, the pendant pentafluorophenyl ester group can be selectively transformed into a variety of other functional groups before or after the ring opening polymerization.
    Type: Grant
    Filed: March 8, 2012
    Date of Patent: June 4, 2013
    Assignees: International Business Machines Corporation, Central Glass Co., Ltd.
    Inventors: Masaki Fujiwara, James Lupton Hedrick, Daniel Paul Sanders, Yoshiharu Terui, Manabu Yasumoto
  • Patent number: 8455592
    Abstract: Disclosed is a polycondensation process for preparing block copolyesters comprising blocks of fluoroether functionalized aromatic polyester and blocks of unmodified polyester. According to the process, a non-fluorinated poly(alkylene arylate) first homopolymer and a fluoroether functionalized poly(alkylene arylate) second homopolymer are combined to form a reaction mixture; the reaction mixture is heated to a temperature above the melting temperatures of each said homopolymer to prepare a molten reaction mixture; and the reaction is continued until the desired molecular weight is achieved. The block copolymers incorporated into blends with unmodified aromatic polyester impart oil and soil resistance to shaped articles prepared from the blends.
    Type: Grant
    Filed: November 8, 2011
    Date of Patent: June 4, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Neville Everton Drysdale, Elizabeth Forrester Mccord, Fredrik Nederberg
  • Patent number: 8444899
    Abstract: Materials and Methods are provided for fabricating microfluidic devices. The materials include low surface energy fluoropolymer compositions having multiple cure functional groups. The materials can include multiple photocurable and/or thermal-curable functional groups such that laminate devices can be fabricated. The materials also substantially do not swell in the presence of hydrocarbon solvents.
    Type: Grant
    Filed: April 3, 2012
    Date of Patent: May 21, 2013
    Assignee: The University of North Carolina at Chapel Hill
    Inventors: Joseph M. DeSimone, Jason P. Rolland, Ginger M. Denison Rothrock, Paul Resnick
  • Patent number: 8410034
    Abstract: Provided is an ether composition containing at least two ether compounds each of which has from 1 to 4 groups represented by formula (X) and from 0 to 3 groups represented by formula (Z), where the total number of groups represented by formula (X) and (Z) is 4: HO—(CH2CH2O)a.(CH2CH(OH)CH2O)b-Q-??(X), CF3(CF2)sO(CF2CF2O)g—??(Z), where a, b, s, g and Q are defined herein. The ratio (CF3/(OH+CF3)) of the total molar amount of CF3 groups in the groups represented by formula (Z) to the sum of the total molar amount of CF3 groups in the groups represented by formula (Z) and the total molar amount of OH groups in the groups represented by formula (X) is from 0.01 to 0.5.
    Type: Grant
    Filed: June 3, 2010
    Date of Patent: April 2, 2013
    Assignee: Asahi Glass Company, Limited
    Inventor: Daisuke Shirakawa
  • Patent number: 8394882
    Abstract: An improved process for emulsion polymerization of fluoropolymers, such as polytetrafluoroethylene, employs reduced amounts of fluorinated emulsifiers. The addition of europium III chloride facilitates emulsion polymerization of fluoropolymers having comparable quality to those fluoropolymers made using conventional processes employing greater amounts of environmentally undesirable fluorinated emulsifiers.
    Type: Grant
    Filed: March 22, 2011
    Date of Patent: March 12, 2013
    Inventor: Zancy VonHooks
  • Patent number: 8378061
    Abstract: Provided are films made from copolyesters having improved oil repellency as compared to conventional copolyesters. The copolyesters are derived from certain perfluorinated monomers.
    Type: Grant
    Filed: September 1, 2010
    Date of Patent: February 19, 2013
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Neville Everton Drysdale, Surbhi Mahajan, Kenneth Gene Moloy, Fredrik Nederberg, Joel M. Pollino, Joachim C. Ritter
  • Patent number: 8362167
    Abstract: The invention provides a compound and tautomeric forms thereof having the formula: wherein Rf1 is selected from the group consisting of hydrogen, a straight chain, branched secondary or branched tertiary C1-C20 perfluoroalkyl group optionally containing ether or thioether linkages and C1-C10 perfluoroalicyclic group optionally containing ether or thioether groups; Rf2 is a straight or branched C1-C20 perfluoroalkylene group optionally substituted with ether and thiother linkages; and X is selected from the group consisting of fluorine and The invention also provides perfluoroelastomeric compositions cured with the perfluoroimidoylamidines of the invention as well as combinations of perfluoroimidoylamidines and other curing agents.
    Type: Grant
    Filed: July 10, 2007
    Date of Patent: January 29, 2013
    Assignee: LODESTAR Inc.
    Inventors: Gubanov Viktor Andreevich, Kollar Alexander Nikolaevich, Volkova Margarita Alekseevna, Tsipkina Irina Mikhailovna
  • Patent number: 8357772
    Abstract: Provided is a terminally iodized polyfluoroalkane represented by the general formula: CnF2n+1(CHXCFY)s+p(CF2CF2)t+rI??[I] (in the formula, X and Y are each a hydrogen atom or a fluorine atom, wherein when Y is a fluorine atom, X is also a fluorine atom; n is an integer of 1 to 6; s+p is an integer of 1 to 5 and denotes the number of CHXCFY group; and t+r is 0 or an integer of 1 to 6 and denotes the number of tetrafluoroethylene skeleton). The terminally iodized polyfluoroalkane is produced by telomerizing a fluorine-containing olefin CHX?CFY and tetrafluoroethylene, successively, to CnF2n+1I in the presence of a peroxide initiator.
    Type: Grant
    Filed: August 29, 2008
    Date of Patent: January 22, 2013
    Assignee: Unimatec Co., Ltd.
    Inventors: Masayosi Horiuti, Seiichiro Murata, Katsuyuki Sato
  • Patent number: 8349523
    Abstract: To provide an electrolyte membrane having excellent dimensional stability even upon absorption of water, a high proton conductance and high power generation performance; and a process for producing the electrolyte membrane with a high productivity. An electrolyte membrane for polymer electrolyte fuel cells, which is made mainly of an ion exchange resin and reinforced with a nonwoven fabric made of fiber of a fluororesin wherein at least some of intersecting points of the fiber are fixed, and which has, as the outermost layer on one side or each side, a layer not reinforced, made of an ion exchange resin which may be the same as or different from the above ion exchange resin, wherein the fluororesin is an ethylene/tetrafluoroethylene copolymer having a melting point of at most 240° C., and the above fixing is fixing by fusion of the fiber.
    Type: Grant
    Filed: March 20, 2009
    Date of Patent: January 8, 2013
    Assignee: Asahi Glass Company, Limited
    Inventors: Seigo Kotera, Hiroyuki Watabe, Shigeru Aida
  • Patent number: 8344192
    Abstract: The invention provides a technique enabling the separation and recovery of an unreacted fluoromonomer from an aqueous fluoropolymer dispersion obtained by emulsion polymerization, without using any extraction solvent, and enabling the prevention of a hydrolysis of —SO2F and a like sulfonic acid precursor functional group convertible to sulfonic acid group. Thus, the invention provides a recovering method fluoromonomer having a sulfonic acid precursor functional group convertible to a sulfonic acid group and remaining unreacted from an aqueous fluoropolymer dispersion obtained by emulsion polymerization of the fluoromonomer, wherein the unreacted fluoromonomer is recovered from the aqueous fluoropolymer dispersion by evaporation, wherein the aqueous fluoropolymer dispersion has an acidic pH.
    Type: Grant
    Filed: December 7, 2007
    Date of Patent: January 1, 2013
    Assignee: Daikin Industries, Ltd.
    Inventors: Tadaharu Isaka, Tadashi Ino, Masaharu Nakazawa, Masahiro Kondo
  • Patent number: 8318869
    Abstract: A composition useful for imparting durable stain repellence and soil release properties to textile substrates, a method for treating textile substrates using such composition, and the textile substrates obtained therefrom. The composition comprises: (A) at least one fluorinated ionisable polyurethane polymer (PUR) being free from perfluoroalkyl chains and comprising at least one fluorinated block comprising a fluoropolyoxyalkene chain, and at least one functional block comprising an hydrocarbon chain (RHC) having from 2 to 14 carbon atoms, said chain (RHC) comprising at least one ionisable group, said blocks being linked by urethane moieties of formula (I), wherein E is a divalent hydrocarbon carbon group; (B) at least one fluorocarbon polymer (F) comprising at least one perfluoroalkyl chain (Rf) linked by one or more ester moiety of formula (II) and/or urethane moiety of formula (III) and/or urea moiety of formula (IV); and (C) at least one crosslinking agent.
    Type: Grant
    Filed: May 13, 2008
    Date of Patent: November 27, 2012
    Assignee: Solvay Solexis S.p.A.
    Inventors: Antonio Russo, Piero Gavezotti, Michael Quallo
  • Patent number: 8304515
    Abstract: A process for the purification of a tetraol PFPE derivative [tetraol (T)] of formula (I): HO—CH2—CH(OH)—CH2—O—CH2—CF2—O—Rf—CF2—CH2O—CH2—CH(OH)—CH2OH, wherein Rf represents a fluoropolyoxyalkene chain (chain Rf), from a mixture (M) of hydroxyl (per)fluoropolyether derivatives, said mixture comprising said tetraol (T) and at least one hydroxyl (per)fluoropolyether [PFPE (OH)] comprising a chain Rf terminated with at least one end group of formula: —CF2CH2OH; —CF2CH2O—CH(OH)—CH2—O—CH2—CH(OH)—CH2OH; said process comprising: step 1: reacting the mixture (M) with ketones and/or aldehydes so as to selectively protect couples of hydroxyl groups on vicinal carbon atoms by forming corresponding cyclic ketal/acetal derivatives, so as to yield a protected mixture (P); step 2: reacting residual hydroxyl groups of the mixture (P) with suitable functionalizing agents enabling substantial volatility modification, so as to obtain a functionalized protected mixture (Pf); step 3: fractional distillation of the mixture (Pf) so a
    Type: Grant
    Filed: March 13, 2009
    Date of Patent: November 6, 2012
    Assignee: Solvay Solexis S.p.A.
    Inventors: Claudio Tonelli, Graziano Giuseppe Vezzulli, Rosaldo Picozzi, Piero Gavezotti
  • Patent number: 8304513
    Abstract: Disclosed are polyesters, particularly poly(trimethylene terephthalate), comprising fluorovinylether functionalized aromatic repeat units, and methods to make the polyester polymers. The polymers are useful for imparting soil resistance to polyesters, particularly in the form of fibers, fabrics, and carpets.
    Type: Grant
    Filed: September 1, 2010
    Date of Patent: November 6, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventors: Neville Everton Drysdale, Surbhi Mahajan, Kenneth Gene Moloy, Fredrik Nederberg, Joel M. Pollino, Joachim C. Ritter
  • Patent number: 8283438
    Abstract: A process for the preparation of functional molecules using the thiol-ene coupling reaction and a process for the preparation of protected functional thiols, specifically thioesters is provided. The methods may be used to make functional polymers and other molecules. The method of making a functionalized polymer using a thiol-ene reaction comprises: providing a functionalized thioester having the following formula: wherein R is a functional group and COR? is a protecting group; cleaving the functionalized thioester, forming a functional thiol and an acyl group; providing a polymer having a pendant vinyl group; and reacting the polymer with the functional thiol whereby a functionalized polymer is formed, wherein the functional thiol is not isolated prior to reacting with the polymer.
    Type: Grant
    Filed: December 6, 2010
    Date of Patent: October 9, 2012
    Assignee: California Institute of Technology
    Inventors: Ralph L. David, Julia A. Kornfield
  • Publication number: 20120251843
    Abstract: Compositions including one or more a central cores having a cyclic group, and a plurality of arms extending from the central cores, wherein the arms comprise perfluoropolyethers (PFPEs) or its derivatives. Methods of preparing the compositions are also provided. Methods of preparing storage media that incorporate the compositions therein are further provided.
    Type: Application
    Filed: March 31, 2011
    Publication date: October 4, 2012
    Applicant: SEAGATE TECHNOLOGY LLC.
    Inventors: XIAOPING YAN, Michael Joseph Stirniman, Jiping Yang, Wenhong Liu, Qian Guo
  • Patent number: 8247614
    Abstract: Fluorinated copolymers are prepared via copolycondensation polymerization in a process comprising reacting A) a telechelic fluoroazido compound of formula N3(Y)p—(CH2)n—R—(CH2)m—(Y)pN3, wherein Y is SO, SO2, C6H4, or CO, p=0 or 1, n and m are independently 1 to 4, and R is selected from the group consisting of i) a C3-C10 fluoroalkylene group, ii) a C3-C10 fluoroalkoxylene group, iii) a substituted aryl group, iv) an oligomer comprising copolymerized units of vinylidene fluoride and perfluoro(methyl vinyl ether), v) an oligomer comprising copolymerized units of vinylidene fluoride and hexafluoropropylene, vi) an oligomer comprising copolymerized units of tetrafluoroethylene and perfluoro(methyl vinyl ether), and vii) an oligomer comprising copolymerized units of tetrafluoroethylene and a hydrocarbon olefin with B) a telechelic diyne or dinitrile compound in the presence of copper halide catalyst.
    Type: Grant
    Filed: June 17, 2009
    Date of Patent: August 21, 2012
    Assignees: E I du Pont de Nemours and Company
    Inventors: Ming-Hong Hung, Bruno Ameduri, Bernard Boutevin, Aurelien Soules
  • Patent number: 8236923
    Abstract: A method of producing a fluorine-containing polymer, containing conducting an addition polymerization of a fluorine-containing compound having 2 or more terminal fluorine-containing vinyl groups each directly bonded to an oxygen atom per molecule, and a compound having 2 or more groups represented by —XH, where X represents an oxygen atom or a sulfur atom; and a fluorine-containing polymer comprising a repeating unit represented by formula (i): wherein Rf1 represents a perfluoroalkylene group; each of Rf2 and Rf3 independently represents a fluorine atom, a perfluoroalkyl group or a perfluoroalkoxy group; at least two among Rf1, Rf2 and Rf3 may bond to each other to form a ring structure; X represents an oxygen atom or a sulfur atom; and L represents a divalent organic group.
    Type: Grant
    Filed: January 15, 2008
    Date of Patent: August 7, 2012
    Assignee: Fujifilm Corporation
    Inventors: Takayuki Ito, Toshimitsu Sakuma, Masayuki Harada