Fluorine Patents (Class 568/615)
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Patent number: 10233274Abstract: A curable composition contains a polymerizable compound and a polymerization initiator. The polymerization initiator initiates polymerization to cure the polymerizable compound. The curable composition further contains compounds having the following general formulae (1) and (2): wherein X1 is selected from a hydroxy group, a carboxy group, a sulfo group, an amino group, and an alkoxy group, l1 denotes an integer in the range of 0 to 7, m1 denotes an integer in the range of 1 to 5, and n1 denotes an integer in the range of 1 to 16, and X2 is selected from a hydroxy group, a carboxy group, a sulfo group, an amino group, and an alkoxy group, l2 denotes an integer in the range of 0 to 7, m2 denotes an integer in the range of 1 to 5, and n2 denotes an integer in the range of 1 to 16.Type: GrantFiled: May 21, 2013Date of Patent: March 19, 2019Assignee: Canon Kabushiki KaishaInventors: Chieko Mihara, Toshiki Ito, Motoki Okinaka
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Patent number: 10029981Abstract: The present invention provides a process for producing a perfluoropolyoxyalkylene peroxide compound comprising a step of reacting a perfluoroalkene with oxygen, wherein the reaction of the perfluoroalkene with oxygen is performed in a microreactor.Type: GrantFiled: December 8, 2016Date of Patent: July 24, 2018Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Keiichirou Watanabe, Hideki Nakaya, Motohisa Shino, Tatsuya Takakuwa, Kazunori Morimoto
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Patent number: 8975445Abstract: A process for the manufacture of a functional (per)fluoropolyether derivative comprising at least one triazole group, such process comprising: (1) reacting a (per)fluoropolyether hydroxyl derivative having at least one hydroxyl group [derivative (PFPE-OH)] with an activating agent, to yield an activated (per)fluoropolyether hydroxyl derivative comprising at least one activated hydroxyl group [derivative (a-PFPE-OH)];(2) reacting said activated (per)fluoropolyether hydroxyl derivative [derivative (a-PFPE-OH)] with at least one azide salt to yield a functional (per)fluoropolyether derivative comprising at least one azido group [derivative (PFPE-N3)] ; and (3) reacting said functional (per)fluoropolyether derivative comprising at least one azido group [derivative (PFPE-N3)] with a hydrocarbon compound having a terminal alkyne group to yield a functional (per)fluoropolyether derivative comprising at least one triazole group [derivative (PFPE-azole)].Type: GrantFiled: April 2, 2010Date of Patent: March 10, 2015Assignee: Solvay Specialty Polymers Italy S.p.A.Inventors: Prakash Wadgaonkar, Shamal Menon, Claudio Adolfo Pietro Tonelli
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Patent number: 8946486Abstract: A method of forming an alkoxylated fluoroalcohol is accomplished by providing a boron compound having or providing at least one boron-oxygen bond and an iodine source. The boron compound and iodine source are combined with reactants of a fluoroalcohol and an alkylene oxide in the presence of a base. The reactants are allowed to react to form an alkoxylated fluoroalcohol reaction product.Type: GrantFiled: December 1, 2008Date of Patent: February 3, 2015Assignee: Tyco Fire & Security GmbHInventor: Thomas Joseph Martin
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Patent number: 8865944Abstract: 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: GrantFiled: May 6, 2010Date of Patent: October 21, 2014Assignee: Solvay Specialty Polymers Italy S.p.A.Inventors: Graziano Giuseppe Vezzulli, Piero Gavezotti, Fabrizio Mutta, Claudio Adolfo Pietro Tonelli
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Publication number: 20140234666Abstract: A novel lubricant comprising a perfluoropoyether (PFPE) molecule terminated with a benzene molecule or a functional benzene molecule for a magnetic recording media structure is disclosed. The magnetic recording media structure includes a substrate, a magnetic recording layer for recording information disposed over the substrate, a protective overcoat layer for protecting the magnetic recording layer disposed over the magnetic recording layer, and a lubricant layer disposed over the protective overcoat layer and comprising a perfluoropoyether (PFPE) molecule terminated with a benzene molecule or a functional benzene molecule.Type: ApplicationFiled: February 19, 2013Publication date: August 21, 2014Applicant: WD MEDIA, INC.Inventor: WD Media, Inc.
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MAGNETIC MEDIA WITH A LOW MOLECULAR WEIGHT LUBRICATING LAYER FOR USE IN HEAD/MEDIA CONTACT DETECTION
Publication number: 20140198409Abstract: According to various embodiments, a lubricating layer for providing lubrication to a magnetic recording medium includes a perfluoropolyether (PFPE) represented by: X—CF2CF2O(C3F6O)mCF2CF2—X, wherein m is in a range from 4 to 8 on average, and wherein X is This lubricating layer may be used in a magnetic disk, which includes a recording layer positioned above a nonmagnetic substrate, a protective film layer positioned above the recording layer, and the lubricating layer positioned above the protective film layer.Type: ApplicationFiled: January 15, 2013Publication date: July 17, 2014Applicant: HGST NETHERLANDS B.V.Inventors: Yoshihiko Ooeda, Hiroyuki Matsumoto, Sukefumi Ito, Yoko Saito -
Publication number: 20140135244Abstract: The invention relates to (per)fluoropolyether block copolymers comprising: A) a fluoropolyoxyalkylene segment (chain Ra) comprising one or more units of formula (CHXCF2CF2O)— in which X is hydrogen or fluorine; B) a (per)fluoropolyoxyalkylene segment (chain Rf), that is to say a segment comprising recurring units having at least one catenary ether bond and at least one fluorocarbon moiety, said (per)fluoropolyoxyalkylene segment being different from chain Ra and having a molecular weight higher than 400 g/mol. These copolymers are endowed with improves lubricant properties or with improved water and oil-repellence properties.Type: ApplicationFiled: June 20, 2012Publication date: May 15, 2014Applicant: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.Inventors: Claudio Adolfo Pietro TONELLI, Simonetta Antonella FONTANA, Marco GALIMBERTI, Piero GAVEZOTTI
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Publication number: 20140123876Abstract: The invention relates to a hydroxy compound of formula (I) wherein n is an integer equal to or higher than 1 as an intermediate for the preparation of compounds of formulae (IIa) and (IIIb) as defined in the specification that can be used as water and oil resistance agents. The invention further relates to water and oil resistance compositions containing compounds (IIa) and (IIb).Type: ApplicationFiled: June 1, 2012Publication date: May 8, 2014Applicant: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.Inventors: Simonetta Antonella Fontana, Claudio Adolfo Pietro Tonelli, Piero Gavezotti
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Patent number: 8648217Abstract: A modified carbonaceous material having chemically bound on its surface at least one fluoropolyoxyalkylene chain (chain Rf) and a process for the modification of a carbonaceous material [material (C)]. The process comprises: contacting the material (C) with a (per)fluoropolyether peroxide comprising at least one peroxidic moiety comprised between sp3 carbon atoms and at least one fluoropolyoxyalkene chain (chain Rf), i.e. a fluorocarbon segment comprising ether linkages in main chain [peroxide (P)]; and heating the material (C) while in contact with the peroxide (P) at a temperature exceeding decomposition temperature of the peroxide (P).Type: GrantFiled: August 4, 2008Date of Patent: February 11, 2014Assignee: Solvay Solexis S.p.A.Inventors: Walter Navarrini, Maurizio Sansotera, Pierangelo Metrangolo, Pietro Cavallotti, Giuseppe Resnati
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Patent number: 8591761Abstract: An apparatus is provided that includes a device and a mechanism for heat transfer that includes a provided hydrofluoroether having high temperature stability. Also provided is a method of transferring heat and a composition that includes a provided hydrofluoroether.Type: GrantFiled: August 13, 2012Date of Patent: November 26, 2013Assignee: 3M Innovative Properties CompanyInventors: Richard M. Flynn, Michael G. Costello, Michael J. Bulinski
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Patent number: 8513471Abstract: A process for the manufacture of a polyol (per)fluoropolyether derivative comprising: 1. reacting at least one triol having two protected hydroxyl functions and a free hydroxyl group with an activating agent, to yield an activated protected triol; 2. reacting the activated protected triol with a functional (per)fluoropolyether derivative of formula: T2-O—Rf-T1, wherein: Rf represents a fluoropolyoxyalkene chain which is a fluorocarbon segment comprising ether linkages in main chain; T1 and T2, equal to or different from each other, are independently selected from non-functional groups of formula: —CF3, —CF2—CF3, —CF2Cl, —CF2CF2Cl, —CF2—COF, —COF: and functional hydroxyl groups comprising at least one hydroxyl group, with the provisio that at least one of T1 and T2 is a functional hydroxyl group as above detailed to yield a protected polyol (per)fluoropolyether derivative; and 3. deprotecting the protected polyol (per)fluoropolyether derivative to yield the polyol (per)fluoropolyether derivative.Type: GrantFiled: October 3, 2008Date of Patent: August 20, 2013Assignee: Solvay Solexis S.p.A.Inventors: Claudio Tonelli, Graziano Giuseppe Vezzulli, Rosaldo Picozzi, Piero Gavezotti, Antonella Di Meo
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Patent number: 8481774Abstract: Provided is a method for producing a tetrafluoro nitrogen-containing heterocyclic compound such as tetrafluoropyrrolidine in good yield and at low cost. The method comprises the steps of: (A) reacting a compound represented by the formula (I) with fluorine gas to produce a tetrafluoro compound represented by the formula (II), (B) converting the tetrafluoro derivative represented by the formula (II) to a compound represented by the formula (III), and (C) reacting the compound represented by the formula (III) with an amine compound represented by the formula NH2R9 to produce a tetrafluoro nitrogen-containing heterocyclic compound represented by the formula (IV) or salt thereof.Type: GrantFiled: October 2, 2009Date of Patent: July 9, 2013Assignee: Nippon Soda Co., Ltd.Inventor: Yasuhiro Miyashita
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Patent number: 8323524Abstract: An apparatus is provided that includes a device and a mechanism for heat transfer that includes a provided hydrofluoroether having high temperature stability. Also provided is a method of transferring heat and a composition that includes a provided hydrofluoroether.Type: GrantFiled: October 1, 2009Date of Patent: December 4, 2012Assignee: 3M Innovative Properties CompanyInventors: Richard M. Flynn, Michael G. Costello, Michael J. Bulinski
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Patent number: 8304576Abstract: Halogenated ?-fluoroethers (or bis-derivatives thereof) can be produced by reacting a halogenated hemiacetal (or bis-derivative thereof) with sulfuryl fluoride (SO2F2) in the presence of an organic base. The reaction is conducted preferably in the presence of “a salt or complex of an organic base with hydrogen fluoride”, whereby the objective dehydroxyfluorination can proceed extremely favorably. It is still preferable to use as the starting substrate a halogenated hemiacetal prepared from fluoral or 3,3,3-trifluoropyruvic acid ester. Thus, industrially important halogenated ?-fluoroethers can be industrially produced with high selectivity and in high yield.Type: GrantFiled: May 14, 2009Date of Patent: November 6, 2012Assignee: Central Glass Company, LimitedInventors: Akihiro Ishii, Manabu Yasumoto
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Publication number: 20120259143Abstract: Disclosed is a fluorinated alkylalkoxylate compound of Formula 1, Rf—O—(CF2)x(CH2)y—O—(QO)z—H ??(1) wherein Rf is a linear or branched perfluoroalkyl having 1 to 6 carbon atoms optionally interrupted by one to three ether oxygen atoms; x is an integer of 1 to 6; y is an integer of 1 to 6; Q is a linear 1,2-alkylene group of the formula CmH2m where m is an integer of 2 to 10; and z is an integer of 1 to 30.Type: ApplicationFiled: April 7, 2011Publication date: October 11, 2012Applicant: E.I. DU PONT DE NEMOURS AND COMPANYInventors: Kenneth Gene Moloy, Sheng Peng, Sourav Kumar Sengupta
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Patent number: 8278256Abstract: Polymers of formula Q-O-[A-B]z-[A-B?]z-A-Q???(I) wherein: A=-(X)a—O-A?-(X?)b— with A?=perfluoropolyether chain and X, X?=—CF2—, —CF2CF2—; a, b=0.1 with the proviso that a=1 if A is linked to Q-O—; b=0 when A is linked to Q?; B derives from homopolymerizable olefins by radical route, of formula: —[(CR1R2—CR3R4)j(CR5R6—CR7R8)j?]—??(Ia) wherein j is an integer from 1 to 30, j? is an integer from 0 to 29 with the proviso that (j+j?) is higher than 2 and lower than 30; R1-R8 are halogen; H; C1-C6 (per)haloalkyl; C1-C6 alkyl; or C1-C6 oxy(per)fluoroalkyl; B?=B but at least one among R1-R8 has a meaning different from that in B; z, z? are such that the number average molecular weight of the polymer of formula (I) is between 500 and 150,000; Q, Q?=C1-C3 (per)fluoroalkyl or functional end group —(CFW)-Dq-Tk; W=F, CF3; k and q are integers, k ranges from 1 to 4, q is an integer and is equal to 0 or 1; with the proviso that at least one of Q, Q? is functional end group.Type: GrantFiled: November 29, 2007Date of Patent: October 2, 2012Assignee: Solvay Solexis S.p.A.Inventors: Giuseppe Marchionni, Pier Antonio Guarda, Marco Avataneo
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Patent number: 8258090Abstract: Fluorinated lubricants of formula: T-O-[A-B]z-[A-B?]z?-A-T???(I) wherein: A=—(X)a—O-A?-(X?)b wherein A? is a perfluoropolyether chain comprising units (CF2O), (CF2CF2O), (CF2CF2CF2O), (CF2CF2CF2CF2O); X, X?=—CF2—, —CF2CF2—; a, b=0 or 1; B derives from olefins, of which at least one homopolymerizable by radical route, of formula: —[(CR1R2—CR3R4)j(CR5R6—CR7R8)j?]—??(Ia) wherein j=1-5, j?=0-4 and 2<(j+j?)<5; R1-R8=halogen, H, C1-C6 (per)haloalkyl, C1-C6 alkyl, C1-C6 oxy(per)-fluoroalkyl; z?2; z? is 0 or an integer; z, z? are such that the number average molecular weight of the polymer of formula (I) is in the range 500-500,000; B?=(Ia) but at least one of R1-R8 has a meaning different than that in B and 2?(j+j?)<5; T, T?=C1-C3 perfluoroalkyl, C1-C6 alkyl and compositions thereof.Type: GrantFiled: November 29, 2007Date of Patent: September 4, 2012Assignee: Solvay Solexis S.p.A.Inventors: Marco Avataneo, Pier Antonio Guarda, Giuseppe Marchionni, Patrizia Maccone, Giovanni Boccaletti
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Patent number: 8247614Abstract: 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: GrantFiled: June 17, 2009Date of Patent: August 21, 2012Assignees: E I du Pont de Nemours and CompanyInventors: Ming-Hong Hung, Bruno Ameduri, Bernard Boutevin, Aurelien Soules
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Patent number: 8217126Abstract: Disclosed herein are novel fluoroolefins of formula Rf—O—(CF2CF2)n(CH2CF2)m—CH?CH2, wherein n is 1 or 2, m is 0 or 1 and Rf is a C1-C8 fluoroalkyl or fluoroalkoxy group. The fluoroolefins may be oxidized to manufacture fluorinated carboxylic acids. Also disclosed are fluoropolymers comprising copolymerized units of the fluoroolefins of the invention and at least one other fluoromonomer.Type: GrantFiled: October 14, 2008Date of Patent: July 10, 2012Assignee: E I du Pont de Nemours and CompanyInventors: Ming-Hong Hung, Sheng Peng
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Publication number: 20120148875Abstract: A magnetic disk with which further reduction of magnetic spacing can be realized and which has high reliability under such circumstances of a lower floating amount of a magnetic head involved in the recent rapid increase in recording density and of extremely severe environmental resistance involved in diversification in use applications is provided.Type: ApplicationFiled: June 22, 2011Publication date: June 14, 2012Applicant: WD MEDIA (SINGAPORE) PTE. LTD.Inventors: Katsushi Hamakubo, Kae Itoh, Koichi Shimokawa
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Patent number: 8173848Abstract: A compound comprising Formula 5 RfOCFHCF2O(CH2CH2O)v—H??Formula 5 wherein Rf is CcF(2c+1); c is 2 to about 6; and v is 2 to about 4; and a process for its preparation comprising contacting a compound of Formula 6 Rf—O—CF?CF2??Formula 6 wherein Rf is CcF(2c+1), and c is 2 to about 6, with a compound of Formula 7 HO—(CH2CH2O)v—H??Formula 7 wherein v is 2 to about 4.Type: GrantFiled: July 1, 2008Date of Patent: May 8, 2012Assignee: E.I. du Pont de Nemours and CompanyInventor: Stephan James Mclain
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Publication number: 20120090504Abstract: Disclosed is a graft copolymer in which a polyalkylene glycol or an alkyl ether thereof is graft-copolymerized with a polyfluoro-1-alkene represented by the general formula: CnF2n+(CH2CF2)a(CF2CF2)bCH?CH2 (wherein n is an integer of 1 to 6, a is an integer of 1 to 4, and b is an integer of 1 to 3). The graft copolymer is an oligomer compound having a perfluoroalkyl group containing 6 or less carbon atoms, which is said to have low bioaccumulation potential, and having, when used as an active ingredient of a mold-releasing agent, mold release performance equivalent to that of a compound having a perfluoroalkyl group containing 8 or more carbon atoms.Type: ApplicationFiled: June 3, 2010Publication date: April 19, 2012Applicant: UNIMATEC CO., LTD.Inventors: Yoshiyama Kaneumi, Seiichiro Murata, Katsuyuki Sato
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Publication number: 20110319516Abstract: Release agents with increased affinity toward nano-imprint lithography template surfaces interact strongly with the template during separation of the template from the solidified resist in a nano-imprint lithography process. The strong interaction between the surfactant and the template surface reduces the amount of surfactant pulled off the template surface during separation of a patterned layer from the template in an imprint lithography cycle. Maintaining more surfactant associated with the surface of the template after the separation of the patterned layer from the template may reduce the amount of surfactant needed in a liquid resist to achieve suitable release of the solidified resist from the template during an imprint lithography process. Strong association of the release agent with the surface of the template facilitates the formation of ultra-thin residual layers and dense fine features in nano-imprint lithography.Type: ApplicationFiled: September 7, 2011Publication date: December 29, 2011Applicant: MOLECULAR IMPRINTS, INC.Inventors: Frank Y. Xu, Weijun Liu
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Patent number: 8071696Abstract: The invention relates to novel crosslinkable copolymers of formula wherein the variables are as defined in the claims. The copolymers of the invention are especially useful for the manufacture of biomedical moldings, for example ophthalmic moldings such as in particular contact lenses.Type: GrantFiled: April 28, 2011Date of Patent: December 6, 2011Assignee: Novartis AGInventors: Thomas Hirt, Jacalyn Marie Schremmer, Troy Vernon Holland, Dieter Lohmann
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Patent number: 8058481Abstract: Described is a process for the alkoxylation of alcohols with I, Cl, or CH3CO2 endgroups, using alkylene epoxides in the presence of boron based catalysts.Type: GrantFiled: April 30, 2009Date of Patent: November 15, 2011Assignee: E.I. du Pont de Nemours and CompanyInventors: Kenneth Gene Moloy, James A. Schultz
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Patent number: 8053606Abstract: A fluorinated alkylalkoxylate, and a process for its preparation in which at least one fluorinated alcohol is contacted with at least one alkylene epoxide in the presence of a catalyst system comprising an alkali metal borohydride, and an organic quaternary salt.Type: GrantFiled: April 30, 2009Date of Patent: November 8, 2011Assignee: E.I. du Pont de Nemours and CompanyInventors: Karl Jeffrey Sweetman, Scott Andrew Backer
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Publication number: 20110257073Abstract: A method of making a fluorinated ether includes combining, in a polar aprotic solvent: a fluorinated alcohol represented by the formula X—Rf1CH2OH, and a fluorinated sulfonate ester represented by the formula Rf2CH2OS(?O)2Rf3, and base; and obtaining a fluorinated ether represented by the formula Y—Rf1CH2OCH2Rf2—Y. Rf1 is selected from perfluorinated C1-C10 alkylene groups having from 1 to 10 carbon atoms and partially fluorinated C1-C10 alkylene groups, and derivatives thereof having catenated heteroatom(s). X represents H, F, or an HOCH2— group. Rf2 is selected from perfluorinated C1-C10 alkyl groups and partially fluorinated C1-C10 alkyl groups, and derivatives thereof having catenated heteroatom(s). Rf3 is a C1-C4 alkyl group. Y represents H, F, or an Rf2CH2OCH2— group. A variant method, useful for preparing symmetric fluorinated ethers, is also disclosed. The present disclosure also provides fluorinated ethers preparable according to the methods.Type: ApplicationFiled: June 27, 2011Publication date: October 20, 2011Inventors: Richard M. Flynn, Michael J. Bulinski, Michael G. Costello
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Patent number: 8039677Abstract: The present invention provides a fluorinated alkylalkoxylate of Formula (1) Rf—(CH2CF2)n(CH2)m—(CH2CH2O)p—XH??(1) wherein Rf is a linear or branched perfluoroalkyl group of 1 to 6 carbon atoms; n is an integer from 1 to 4; X is O; m is an integer from 1 to 6; and p is an integer from 1 to about 40; and a method of altering the surface behavior of a liquid with the fluorinated alkylalkoxylate of Formula (1).Type: GrantFiled: April 30, 2009Date of Patent: October 18, 2011Assignee: E.I. du Pont de Nemours and CompanyInventors: Sheng Peng, Sourav Kumar Sengupta
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Publication number: 20110237676Abstract: Provided herein are new spermicidal compositions that include one or more fluorous surfactants, e.g., non-ionic fluorous surfactants, anionic fluorous surfactants, cationic fluorous surfactants, and combinations thereof. Also provided are methods of preventing fertilization of an ovum, which include a step of contacting at least one spermatozoon with one or more fluorous surfactants. Additionally described herein are methods of preventing infection, which include a step of contacting at least one infectious pathogenic microorganism with one or more fluorous surfactants. Numerous fluorine-containing surfactants are demonstrated to be efficacious as human spermicides.Type: ApplicationFiled: August 20, 2008Publication date: September 29, 2011Applicant: LEHIGH UNIVERSITYInventors: Barry Bean, Robert A Flowers, Jennifer J Venditti, Rajni Singh
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Patent number: 8012920Abstract: The present invention provides a lubricant for forming a lubricating layer which is useful in preventing fly and stiction and/or corrosion at an extremely small flying height of 10 nm or less, which is prevented from migrating at a high rotational speed of 5400 rpm or more, which has high adhesion, and which is suitable for a load/unload method. A crude lubricant containing at least one perfluoropolyether is degassed and then purified. Alternatively, a liquid crude lubricant containing at least one perfluoropolyether is purified by vaporizing the crude lubricant and then liquefying the vapor of the perfluoropolyether within a distance less than the mean free path of molecules of the perfluoropolyether. A magnetic disk is prepared in such a manner that a carbonaceous protective layer is formed above a substrate and a lubricating layer is formed on the protective layer using of the lubricant. The lubricant contains the perfluoropolyether and has a molecular weight distribution of 1.3 or less.Type: GrantFiled: January 12, 2005Date of Patent: September 6, 2011Assignee: WD Media (Singapore) Pte. Ltd.Inventor: Koichi Shimokawa
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Publication number: 20110178323Abstract: Provided is a method for producing a tetrafluoro nitrogen-containing heterocyclic compound such as tetrafluoropyrrolidine in good yield and at low cost. The method comprises the steps of: (A) reacting a compound represented by the formula (I) with fluorine gas to produce a tetrafluoro compound represented by the formula (II), (B) converting the tetrafluoro derivative represented by the formula (II) to a compound represented by the formula (III), and (C) reacting the compound represented by the formula (III) with an amine compound represented by the formula NH2R9 to produce a tetrafluoro nitrogen-containing heterocyclic compound represented by the formula (IV) or salt thereof.Type: ApplicationFiled: October 2, 2009Publication date: July 21, 2011Applicant: NIPPON SODA CO., LTD.Inventor: Yasuhiro Miyashita
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Publication number: 20110152567Abstract: To provide a method for producing a perfluoro compound having hydroxyl groups, whereby agglomeration of a reduction reaction intermediate tends not to occur during a reduction reaction, and a perfluoro compound having —C(?O)OH can be used as a starting material. Reducing (A-C(?O)=Q=)nRfn in the presence of a metal hydride and an inorganic salt of lithium in an alcohol solvent to obtain (B—CH(OH)-Q-)n-m,(A-C(?O)-Q-)mRfn, wherein A is a hydroxyl group, a C1-5 alkoxy group, a hydrogen atom, a C1-5 alkyl group or the like, Q is a perfluoroalkylene group or the like, n is an integer of at least 1, m is an integer at least 0 and less than n, Rfn is an n valent perfluoro saturated hydrocarbon group or the like, and B is a group depending on A wherein when A is a hydroxyl group, a C1-5 alkoxy group or the like, B is a hydrogen atom, and when A is a hydrogen atom, a C1-5 alkyl group or the like, B is the same group as A.Type: ApplicationFiled: March 2, 2011Publication date: June 23, 2011Applicant: ASAHI GLASS COMPANY, LIMITEDInventors: Daisuke SHIRAKAWA, Yoshiyuki Gozu, Yoshitomi Morisawa
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Patent number: 7964552Abstract: This invention relates to surfactant compositions comprising a fluorosurfactant and a siloxane surfactant wherein the fluorosurfactant exhibits a disproportionate effect upon the resulting surfactant composition's ability to lower equilibrium surface tension. The fluorosurfactants and siloxane surfactants identified by the present invention exhibit a desirable disproportionate effect from the fluorosurfactant acting upon the resulting surfactant composition's ability to lower equilibrium surface tension. Because of this disproportionate effect, surfactant compositions of the present invention with no more than 21 weight percent fluorosurfactant have nearly identical ability to lower equilibrium surface tensions compared with surfactant compositions having higher amounts of fluorosurfactant.Type: GrantFiled: November 13, 2007Date of Patent: June 21, 2011Assignee: E. I. du Pont de Nemours and CompanyInventors: Axel Hans-Joachim Herzog, Shaun Raymond Rinehimer
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Patent number: 7956135Abstract: The invention relates to novel crosslinkable copolymers of formula wherein the variables are as defined in the claims. The copolymers of the invention are especially useful for the manufacture of biomedical moldings, for example ophthalmic moldings such as in particular contact lenses.Type: GrantFiled: January 21, 2009Date of Patent: June 7, 2011Assignee: Novartis AGInventors: Thomas Hirt, Jacalyn Marie Schremmer, Troy Vernon Holland, Dieter Lohmann
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Publication number: 20110092665Abstract: Process for the oligomerization of hexafluoropropylene oxiyde (HFPO) in which the sum of the dimers, trimers, tetramers, pentamers and hexamers represents less than 20% of the weight of the polymerized HFPO, the oligomers other than the dimers, trimers, tetramers, pentamers and hexamers (the remaining oligomers) having an average molecular weight ranging between 1100 and 4000 g/mol, characterized in that the process comprises the steps of contacting hexafluoropropylene oxide (HFPO) at a temperature between ?30° C. to +50° C.Type: ApplicationFiled: March 25, 2009Publication date: April 21, 2011Applicant: CLARIANT FINANCE (BVI) LIMITEDInventor: Bernard Danner
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Publication number: 20110079043Abstract: An apparatus is provided that includes a device and a mechanism for heat transfer that includes a provided hydrofluoroether having high temperature stability. Also provided is a method of transferring heat and a composition that includes a provided hydrofluoroether.Type: ApplicationFiled: October 1, 2009Publication date: April 7, 2011Inventors: Richard M. Flynn, Michael G. Costello, Michael J. Bulinski
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Patent number: 7737307Abstract: A compound comprising Formula I, or a mixture thereof, Rf—OCFHCF2O—[CH2CH2O]x—[C3H7O]y-A??Formula I wherein Rf is CnF2n+1, n is 1 to about 6, x is a mixture of positive integers and is 4 or greater, y is 0 to about 4, provided that the ratio of y to x is equal to or less than 0.25, A is RfOCHFCF2 or CmH2m+1, and m is 1 to about 24 and its use in lowering surface tension and imparting improved surface effects is disclosed.Type: GrantFiled: August 6, 2007Date of Patent: June 15, 2010Assignee: E. I. du Pont de Nemours and CompanyInventors: Peter Michael Murphy, Andrew Edward Feiring, Stephan James McLain, Jessica Sinks
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Patent number: 7534845Abstract: Fluorovinyl ethers having the formula CFX?CXOCF2OR, wherein R is a C2-C6 linear, branched or C5-C6 cyclic (per) fluoroalkyl group, or a C2-C6 linear, branched (per)fluoro oxyalkyl group containing from one to three oxygen atoms; when R is fluoroalkyl or fluorooxyalkyl group as above defined, it can contain from 1 to 2 atoms, equal or different, selected from the following: H, Cl, Br, I; X?F, H; and homopolymers or polymers obtainable polymerizing said Fluorovinyl ethers with at least another polymerizable monomer.Type: GrantFiled: December 18, 2006Date of Patent: May 19, 2009Assignee: Solvay Solexis S.p.A.Inventor: Walter Navarrini
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Patent number: 7521519Abstract: The invention relates to novel crosslinkable copolymers of formula wherein the variables are as defined in the claims. The copolymers of the invention are especially useful for the manufacture of biomedical molding, for example ophthalmic moldings such as in particular contact lenses.Type: GrantFiled: March 14, 2000Date of Patent: April 21, 2009Assignee: Novartis AGInventors: Thomas Hirt, Jacalyn Marie Schremmer, Troy Vernon Holland, Dieter Lohmann
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Patent number: 7488852Abstract: Processes for the preparation of perfluoropolyethers having structural formula R1O—(CF2O)n—(CF2CF2O)mR2??(I) wherein: R1 is —CH3 or —C2H5; R2 is equal to R1 or —CF2H n is 0 or an integer from 1 to 100; m is an integer from 1 to 100 or, when R2 is —CF2H, m can also be 0; the oxyfluoroalkylene units —(CF2CF2O)— and —(CF2O)— are statistically distributed along the polymer chain.Type: GrantFiled: July 28, 2006Date of Patent: February 10, 2009Assignee: Ausimont S.p.A.Inventors: Giuseppe Marchionni, Mario Visca
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Patent number: 7465837Abstract: Fluorinated vinyl ethers are provided having the structure of formula (I) the structure of formula (I) wherein at least one of X and Y is a fluorine atom, and L, R1, R2, R3, R4 are as defined herein. Also provided are copolymers prepared by radical polymerization of (I) and a second monomer that may not be fluorinated. The polymers are useful in lithographic photoresist compositions, particularly chemical amplification resists. In a preferred embodiment, the polymers are substantially transparent to deep ultraviolet (DUV) radiation, and are thus useful in DUV lithographic photoresist compositions. A method for using the composition to generate resist images on a substrate is also provided, i.e., in the manufacture of integrated circuits or the like.Type: GrantFiled: August 10, 2006Date of Patent: December 16, 2008Assignee: International Business Machines CorporationInventors: Richard A. DiPietro, Hiroshi Ito
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Publication number: 20080306308Abstract: A process for preparing a fluorine-containing alkoxyalkane represented by the general formula (1) R1—O—R2—O—R3 where at least one of R1, R2 and R3 contains one or more fluorine atoms. An alcohol with the highest acidity selected from the group consisting of the compounds represented by the general formula (2) R1—OH, the general formula (3) R3—O—R2—OH, the general formula (4) R1—O—R2—OH, and the general formula (5) R3—OH is reacted with at least one selected from the group consisting of the compounds represented by the general formula (6) Lg-R2—O—R3, the general formula (7) Lg-R1, the general formula (8) Lg-R3, and the general formula (9) Lg-R2—O—R1 where Lg represents an anionic leaving group in the presence of a basic compound.Type: ApplicationFiled: June 4, 2008Publication date: December 11, 2008Inventors: Tetsuo Nanno, Masaki Deguchi
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Patent number: 7408019Abstract: A novel fluorinated ether compound useful as an inert medium is provided. The compound is represented by the following formula (1) such as the compound represented by the following formula (1a) or the compound represented by the following formula (1b): RF1OCFRF2CFRF2ORF1 ??(1) F(CF2)4OCF(CF3)CF(CF3)O(CF2)4F ??(1a) F(CF2)6OCF(CF3)CF(CF3)O(CF2)6F ??(1b) wherein the symbols have the following meanings: RF1 is a C4-7 linear perfluoroalkyl group; and RF2 is a fluorine atom or a trifluoromethyl group.Type: GrantFiled: April 26, 2006Date of Patent: August 5, 2008Assignee: Asahi Glass Company, LimitedInventors: Masao Iwaya, Kazuya Oharu, Hirokazu Takagi, Hidekazu Okamoto
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Patent number: 7393961Abstract: (Per)haloethers having formula: X-(Rf)L-O—CF2CF2—O—CX1X2—CFX3X4 , ??(I) process for obtaining them and hypofluorites usable in the synthesis of said (per)haloethers.Type: GrantFiled: March 8, 2005Date of Patent: July 1, 2008Assignee: Solvay Solexis S.p.A.Inventors: Giovanni Fontana, Walter Navarrini
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Patent number: 7388114Abstract: A novel perfluoropolyether derivative which is less likely to undergo decomposition, which is free from a problem of deterioration during its use, and which is useful as a lubricating oil or a coating agent, is provided. A compound represented by the following formula (1): HO—(CH2CH2O)r. (CH2CH(OH)CH2O)p—CH2CF2O(CF2CF2O)mCF2CH2O——(CH2CH(OH)CH2O)q. (CH2CH2O)s—H ??Formula (1) wherein m represents an integer of from 3 to 200, and each of p, q, r and s which are independent of one another, represents an integer of from 0 to 100, provided that when each of p, q, r and s which are independent of one another, is an integer of at least 1, the arrangement of —(CH2CH2O)— and —(CH2CH(OH)CH2O)— units is not particularly limited, and when one of r and p is an integer of at least 2 and the other is an integer of at least 1, or when one of q and s is an integer of at least 2 and the other is an integer of at least 1, these units may be arranged in a block form or at random.Type: GrantFiled: May 1, 2007Date of Patent: June 17, 2008Assignee: Asahi Glass Company, LimitedInventors: Daisuke Shirakawa, Takashi Okazoe, Kazuya Oharu, Shu-zhong Wang, Koichi Murata, Kengo Kawahara
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Patent number: 7375253Abstract: A process for the synthesis of (per)fluorinated mono-functional carbonyl compounds having the following formula (I): F-A-RF—B—C(O)X1??(I) wherein: X1=F, CF3; A, B equal to or different from each other, are independently (per)fluoroalkylene or (per)fluorooxyalkylene groups; RF is —ORf1O— wherein Rf1=perfluoroalkylene or —ORf2, wherein Rf2 is a perfluorooxyalkylene chain; said process comprising the following steps: A) obtainment of the formula (II) mono-hypofluorite: FO—CFX2-A-RF—B—C(O)X1??(II) by partial fluorination with elemental fluorine of the carbonyl groups of the formula (III) compound: X2(O)C-A-RF—B—C(O)X1??(III) in the presence of a formula MeFy catalyst, Me being an alkaline or alkaline-earth metal or Ag, y=1 or 2; B) thermal decomposition of the compound (II) to give the compounds according to the following scheme: FO—CFX2-A-RF—B—C(O)X1 (II) - - - ?F-A-RF—B—C(O)X1 (I)+(O)CFX2.Type: GrantFiled: January 9, 2004Date of Patent: May 20, 2008Assignee: Solvay Solexis S.p.A.Inventors: Giovanni Fontana, Walter Navarrini
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Patent number: 7288682Abstract: A process for separating bifunctional perfluoropolyethers (PFPEs) having two terminations —CH2OH from their mixtures with monofunctional PFPEs with one termination —CH2OH, of general formula X1—O—Rf—Y ??(I) wherein Rf is a perfluoropolyoxyalkylene chain having a number average molecular weight of 500-10,000; X1 and Y are end groups selected from —CFXCH2OH (wherein X is F or CF3), —CF3, —CF2Cl, —CF2CF2Cl, —C3F6Cl, —CF2Br, —CF2CF3, wherein at least one of the two end groups is —CFXCH2OH, said process comprising the steps of: a) addition of the PFPE mixture to an adsorbing solid phase, under stirring; b) filtration of the mixture obtained in a): c) addition to the solid phase filtered in b), of a PFPE mixture having an average functionality higher than that of the PFPE mixture of the liquid filtered in b); c2) filtration of the mixture obtained in c); and subsequent treatment of the solid phase separated in c2) with a polar solvent obtaining a liquid containing the PFPE having high functionality.Type: GrantFiled: July 8, 2005Date of Patent: October 30, 2007Assignee: Solvay Solexis S.p.A.Inventors: Alexandre Tchistiakov, Simonetta Fontana, Claudio Tonelli
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Patent number: 7232932Abstract: A perfluoropolyether, a composition comprising the perfluoropolyether, a process for producing the perfluoropolyether, and a process for improving the thermostability of grease or lubricant are provided. The perfluoropolyether comprises perfluoroalkyl radical end groups in which the radical has at least 3 carbon atoms per radical and is substantially free of perfluoromethyl and perfluoroethyl end groups. The process for producing the perfluoropolyether can comprise (1) contacting a perfluoro acid halide, a C2-to C4-substituted ethyl epoxide, or a C3+ fluoroketone with a metal halide to produce an alkoxide; (2) contacting the alkoxide with either hexafluoropropylene oxide or tetrafluorooxetane to produce a second acid halide; (3) esterifying the second acid halide to an ester; (4) reducing the ester to its corresponding alcohol; (5) converting the alcohol with a base to a salt form; (6) contacting the salt form with a C3 or higher olefin to produce a fluoropolyether; and (7) fluorinating the fluoropolyether.Type: GrantFiled: March 30, 2004Date of Patent: June 19, 2007Assignee: E. I. du Pont de Nemours and CompanyInventors: Jon L. Howell, Erik William Perez, Alfred Waterfeld, Chadron Mark Friesen, Joseph Stuart Thrasher
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Patent number: 7230140Abstract: A novel perfluoropolyether derivative which is less likely to undergo decomposition, which is free from a problem of deterioration during its use, and which is useful as a lubricating oil or a coating agent, is provided. A compound represented by the following formula (1): HO—(CH2CH2O)r.(CH2CH(OH)CH2O)p—CH2CF2O(CF2CF2O)mCF2CH2O——(CH2CH(OH)CH2O)q.(CH2CH2O)s—H??Formula (1) wherein m represents an integer of from 3 to 200, and each of p, q, r and s which are independent of one another, represents an integer of from 0 to 100, provided that when each of p, q, r and s which are independent of one another, is an integer of at least 1, the arrangement of —(CH2CH2O)— and —(CH2CH(OH)CH2O)— units is not particularly limited, and when one of r and p is an integer of at least 2 and the other is an integer of at least 1, or when one of q and s is an integer of at least 2 and the other is an integer of at least 1, these units may be arranged in a block form or at random.Type: GrantFiled: April 18, 2005Date of Patent: June 12, 2007Assignee: Asahi Glass Company, LimitedInventors: Daisuke Shirakawa, Takashi Okazoe, Kazuya Oharu, Shu-zhong Wang, Koichi Murata, Kengo Kawahara