Fluorine Patents (Class 568/677)
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Patent number: 11427680Abstract: The present invention relates to a novel process for the synthesis of (per)fluoropolyether polymers, to certain novel (per)fluoropolyether polymers. The present invention also relates to the use of the (per)fluoropolyether polymers thus obtained as intermediate compounds for the manufacture of further polymers suitable for use as lubricants, notably for magnetic recording media (MRM).Type: GrantFiled: December 12, 2017Date of Patent: August 30, 2022Assignee: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.Inventors: Cristiano Monzani, Vito Tortelli, Marco Galimberti, Roberto Valsecchi, Patrizia Maccone
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Patent number: 9145471Abstract: The present invention relates to a process for increasing the content of bifunctional species in mixtures of non functional, mono- and bifunctional (per)fluoropolyethers which comprises the adsorption of a (per)fluoropolyether mixture onto an adsorbing stationary phase, a first desorption step with a supercritical fluid only and a second desorption step with the supercritical fluid and a mixture of a polar solvent.Type: GrantFiled: October 23, 2012Date of Patent: September 29, 2015Assignee: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.Inventors: Claudio Adolfo Pietro Tonelli, Roberto Valsecchi, Fabrizio Mutta
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Publication number: 20150148565Abstract: 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: ApplicationFiled: February 3, 2015Publication date: May 28, 2015Inventor: Thomas Joseph Martin
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Publication number: 20150112095Abstract: The present invention is drawn to a compound of formula (1): wherein Rf is C1 to C6 linear or branched fluoroalkyl, X is F or Cl, and R1 is H, CH3, or CH2CH3. The compound can be used to form partially fluorinated alcohols, derivatives, and polymers. Thus, the present invention provides compounds having lower fluorine content, the process for making lower fluorine containing compounds, and derivatives made from lower fluorine containing alcohols.Type: ApplicationFiled: October 17, 2013Publication date: April 23, 2015Applicant: E I DU PONT DE NEMOURS AND COMPANYInventor: ROMAN B. LARICHEV
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Patent number: 8865947Abstract: The present invention is directed to a process for preparation of fluorinated alcohols of Formula (I) RfCH2CH2OH??(I) by contacting a fluorinated iodide with an alkyl vinyl ether in the presence of an initiator and a base to generate an intermediate hemi-acetal or aldehyde or a mixture thereof, followed by hydrogenation of the hemi-acetal of Formula (II) RfCH2CH(OCxH2x+1)m(OH)p??(II) or aldehyde of Formula (III) RfCH2CHO??(III) or a mixture thereof, to yield a compound of Formula (I).Type: GrantFiled: December 6, 2012Date of Patent: October 21, 2014Assignee: E I du Pont de Nemours and CompanyInventors: Kenneth Gene Moloy, Sheng Peng
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Publication number: 20140287240Abstract: To provide a fluorinated ether compound, a fluorinated ether composition and a coating liquid, whereby it is possible to form a surface-treated layer which has high initial water/oil repellency and which is excellent in abrasion resistance and fingerprint stain removability, and a substrate having a surface-treated layer and a method for its production. A fluorinated ether compound which has a poly(oxyperfluoroalkylene) chain (??) having a C4 oxyperfluoroalkylene unit (?) and an oxyperfluoroalkylene unit (?) other than the unit (?) and which has a hydrolysable silyl group on at least one terminal of the poly(oxyperfluoroalkylene) chain (??) via a linking group.Type: ApplicationFiled: June 6, 2014Publication date: September 25, 2014Applicant: ASAHI GLASS COMPANY, LIMITEDInventors: Eisuke MUROTANI, Taiki Hoshino, Akira Isobe, Daisuke Shirakawa, Daisuke Jomuta, Nobuyuki Otozawa
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Publication number: 20140275635Abstract: The present invention relates to a process for increasing the content of bifunctional species in mixtures of non functional, mono- and bifunctional (per)fluoropolyethers which comprises the adsorption of a (per)fluoropolyether mixture onto an adsorbing stationary phase, a first desorption step with a supercritical fluid only and a second desorption step with the supercritical fluid and a mixture of a polar solvent.Type: ApplicationFiled: October 23, 2012Publication date: September 18, 2014Inventors: Claudio Adolfo Pietro Tonelli, Roberto Valsecchi, Fabrizio Mutta
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Publication number: 20130317257Abstract: A surface agent includes two end portions and a middle portion disposed between the end portions. The end portions include a terminal section and a midsection. The terminal section includes at least one surface active functional group. The midsection includes at least one perfluoroethyl ether unit. The middle portion includes at least one perfluorobutyl ether unit.Type: ApplicationFiled: July 30, 2013Publication date: November 28, 2013Applicant: HGST Netherlands B.V.Inventors: John M. Burns, Hong Deng, Xing-Cai Guo, Bruno Marchon, Daryl J. Pocker, Robert Waltman
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Publication number: 20130256588Abstract: A process for fluorinating hydrocarbon compounds, which comprises: A. providing a compound selected from the group consisting of straight-chain, branched-chain and cyclic alkanes, straight-chain, branched-chain and cyclic ethers, said compound comprising at least one carbon-hydrogen bond and being free from C(O)— functional groups; B. reacting said compound with fluorine in the presence of at least one (per)haloolefin comprising at least one carbon-carbon double bond and having at least one fluorine or chlorine atom on either one of the carbon atoms of said double bond, to obtain a compound wherein at least one carbon-hydrogen bond has been replaced by a carbon-fluorine bond. Compositions of partially fluorinated compounds obtained with the process are also disclosed.Type: ApplicationFiled: December 16, 2011Publication date: October 3, 2013Applicant: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.Inventors: Vito Tortelli, Marco Galimberti, Cristiano Monzani, Piero Gavezotti
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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: 8410034Abstract: 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: GrantFiled: June 3, 2010Date of Patent: April 2, 2013Assignee: Asahi Glass Company, LimitedInventor: Daisuke Shirakawa
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Patent number: 8350094Abstract: 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: GrantFiled: June 27, 2011Date of Patent: January 8, 2013Assignee: 3M Innovative Properties CompanyInventors: Richard M. Flynn, Michael J. Bulinski, Michael G. Costello
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Publication number: 20120315504Abstract: A compound of the formula (1), lubricant containing the compound and magnetic disk C6H4—(O—Z—R—X)2??(1) wherein Z is —CH2CH2O— or —CH2CH(OH)CH2O—, R is —CH2CF2CF2CF2O(CF2CF2CF2CF2O)nCF2CF2CF2CH2—, n is a real number of 0 to 20, X is —OH, —O(CH2)mOH, —OCH2CH(OH)CH2OH, —OCH2CH(OH)CH2O—C6H5 or —OCH2CH(OH)CH2O—C6H4—OCH3, m is an integer of 1 to 6.Type: ApplicationFiled: June 4, 2012Publication date: December 13, 2012Inventors: Tsuyoshi SHIMIZU, Nagayoshi KOBAYASHI
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Publication number: 20120298333Abstract: 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: August 13, 2012Publication date: November 29, 2012Inventors: Richard M. Flynn, Michael G. Costello, Michael J. Bulinski
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Patent number: 8217119Abstract: Polymeric compositions comprising: 1) at least one thermoprocessable semicrystalline halo-polymer; 2) an additive in amounts between 0.01 and 10% by weight of 1) one or more (per)fluoropolyether polymers of formula: Q-O-[A-B]z-[A-B?]z?-A-Q???(I) wherein: A=—(X)a—O-A?-(X?)b— wherein A? is a perfluoropolyether chain; X, X?=—CF2—, —CF2CF2—, —CF(CF3)—; a, b=0 or 1; B derives from one or more olefins, of which at least one homopolymerizable by radical way, of formula: —[(CR1R2—CR3R4)j(CR5R6—CR7R8)j?]—??(Ia) wherein j=1-30, j?=0-29, with the proviso that 2<(j+j?)<30; R1-R8=halogen, H, C1-C6 (per)haloalkyl, C1-C6 alkyl, or C1-C6 oxy(per)fluoroalkyl; B?=(Ia) but at least one of R1-R8 has a meaning different from that in B, and 2?(j+j?)<30; z?2; z? is 0 or an integer; z, z? are such that the number average molecular weight of (I) is between 500 and 500,000; Q, Q?=C1-C3 perfluoroalkyl; C1-C6 alkyl; or functional end group(s).Type: GrantFiled: November 26, 2007Date of Patent: July 10, 2012Assignee: Solvay Solexis S.p.A.Inventors: Julio A. Abusleme, Marco Avataneo, Giancarlo Perfetti
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Publication number: 20120127601Abstract: A lubricant compound for a magnetic disk is provided which can realize further reduction of the magnetic spacing and moreover, has high reliability under a lower floating amount of the magnetic head involved with the recent rapid increase in the recording density and under extremely severe environmental resistance involved with diversification of the applications. A lubricant compound is contained in a lubrication layer of a magnetic disk in which at least a magnetic layer, a protective layer, and a lubrication layer are sequentially provided on a substrate, and the lubricant compound contains a component A and a component B expressed by the following chemical formula: [Chemical formula] 1 Component A: X=OH Component B: X=OCH2CH(OH)CH2OH and a component C made of a specific compound having a phosphezene ring in the structure thereof.Type: ApplicationFiled: March 27, 2010Publication date: May 24, 2012Applicant: WD MEDIA (SINGAPORE) PTE. LTD.Inventors: Kota Suzuki, Koichi Shimokawa, Katsushi Hamakubo, Kae Itoh
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Patent number: 8178480Abstract: A lubricant for magnetic disks which can form a lubricating layer having a reduced thickness while attaining a high coverage and is excellent in heat resistance and adhesion to a protective layer. The lubricant for magnetic disks comprises a perfluoropolyether compound in which the relationship between the number-average molecular weight and the standardized value of the number of hydroxy groups contained in the molecule satisfies the following: the number-average molecular weight is in the range of 1,000-6,000; the standardized value of the number of hydroxy groups contained in the molecule is 180 or higher; and the compound is in a region located below the line connecting the point where the number-average molecular weight is 1,000 and the standardized value of the number of hydroxy groups in the molecule is 400 to the point where the number-average molecular weight is 6,000 and the standardized value of the number of hydroxy groups in the molecule is 1,600.Type: GrantFiled: September 28, 2007Date of Patent: May 15, 2012Assignee: WD Media (Singapore) Pte. Ltd.Inventors: Katsushi Hamakubo, Koichi Shimokawa, Kota Suzuki
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Publication number: 20120059144Abstract: 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: ApplicationFiled: May 6, 2010Publication date: March 8, 2012Applicant: SOLVAY SOLEXIS S.P.A.Inventors: Claudio Adolfo Pietro Tonelli, Graziano Giuseppe Vezzulli, Rosaldo Picozzi, Piero Gavezotti
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Publication number: 20120040189Abstract: To provide a surface treating agent and a composition for surface treatment capable of forming a coating film excellent in the water/oil repellency, the efficiency for removal of oil-and-fat stains, alkali resistance and heat resistance and having a low coefficient of friction; a method for treating the surface of an article by using the surface treating agent or the composition for surface treatment; an article having surface treatment applied; and a novel fluorinated ether compound useful as a surface treating agent. A surface treating agent comprising a compound represented by the following formula (A): RFO(CF2CF2O)aCF2C(O)N(H)b(-Q-OC(O)C(R)?CH2)2-b??(A) wherein RF is a C1-20 perfluoro monovalent saturated hydrocarbon group or the like; a is an integer of from 1 to 200; b is 0 or 1; Q is a C1-6 alkylene group or the like; and R is a hydrogen atom or a C1-3 alkyl group.Type: ApplicationFiled: October 21, 2011Publication date: February 16, 2012Applicant: Asahi Glass Company, LimitedInventors: Daisuke Shirakawa, Yoshiyuki Gozu, Taiki Hoshino
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Patent number: 8071816Abstract: The present disclosure provides a compound according to the formula: Rf1[CH(—O—CH(3-m)Rf2m)(—O—CF2—CFH—Rf3)]n ??[I] wherein n is 1 or 2, wherein m is 1, 2 or 3, wherein, when n is 1, Rf1 is selected from the group consisting of highly fluorinated alkyl groups which are linear, branched, cyclic, or a combination thereof, which may optionally be substituted, and which may optionally contain one or more catenated heteroatoms; wherein, when n is 2, Rf1 is selected from the group consisting of highly fluorinated alkylene groups which are linear, branched, cyclic, or a combination thereof, which may optionally be substituted, and which may optionally contain one or more catenated heteroatoms; wherein each Rf2 is independently selected from the group consisting of alkyl groups which are linear, branched, cyclic, or a combination thereof, which may optionally be substituted, and which may optionally contain one or more catenated heteroatoms; wherein at least one Rf2 is highly fluorinated; wherein each Rf3 is indepeType: GrantFiled: June 30, 2008Date of Patent: December 6, 2011Assignee: 3M Innovative Properties CompanyInventors: Richard M. Flynn, Michael G. Costello
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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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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: 20110213113Abstract: RF-compositions including surfactants, foam stabilizers, monomers, polymers, urethanes, intermediates, metal complexes, phosphate esters as well as telomerization methods are provided.Type: ApplicationFiled: May 6, 2011Publication date: September 1, 2011Applicant: E. I. DU PONT DE NEMOURS AND COMPANY CHEMTURA CORPORATIONInventors: Andrew Jackson, Vimal Sharma, E. Bradley Edwards, Janet Boggs, Vicki Hedrick, Stephan Brandstadter, John Chien, Edward Norman, Robert Kaufman, Bruno Ameduri, George K. Kostov
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Patent number: 7988877Abstract: 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: GrantFiled: November 3, 2008Date of Patent: August 2, 2011Assignee: 3M Innovative Properties CompanyInventors: Richard M. Flynn, Michael J. Bulinski, Michael G. Costello
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Publication number: 20110165037Abstract: A microfluidic system comprising a microchannel, a carrier fluid comprising a fluorinated oil in the microchannel, at least one plug comprising an aqueous plug-fluid in the microchannel and substantially surrounded on all sides by the carrier-fluid, and a fluorinated surfactant comprising a functional group capable of selectively binding a target molecule is disclosed. A compound for use therewith and a method of synthesizing a fluorinated surfactant are also provided.Type: ApplicationFiled: January 7, 2011Publication date: July 7, 2011Inventors: Rustem F. Ismagilov, Jason Eugene Kreutz
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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: 7956023Abstract: Provided is a lubricant solution for a magnetic recording media, wherein the lubricant solution includes a lubricant that is excellent in chemical stability and capable of imparting excellent lubricity to the lubricant solution, and a solvent having a suitable dissolving power for the lubricant, being excellent in drying properties and not influential over the ozone layer. Also provided is a lubricant solution including a lubricant and a fluorinated alkyl ether. Further provided is a lubricant solution including a compound of the formula (HO—CH2—CF2(OCF2CF2)dO—)3Y, wherein Y is a trivalent perfluorohydrocarbon group, as the lubricant and 1,1,2,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether as the fluorinated alkyl ether.Type: GrantFiled: January 24, 2007Date of Patent: June 7, 2011Assignee: Asahi Glass Company, LimitedInventors: Daisuke Shirakawa, Hidekazu Okamoto
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Publication number: 20110067957Abstract: A method of lubricating a wind turbine gearbox comprising using a lubricating composition comprising at least one (i.e. one or a mixture of more than one) perfluoropolyether (PFPE) lubricant which comprises a perfluorooxyalkylene chain, said perfluorooxyalkylene chain comprising recurring units having at least one ether bond and at least one fluorocarbon moiety. A wind turbine gearbox comprising a lubricating system containing said lubricating composition.Type: ApplicationFiled: May 15, 2009Publication date: March 24, 2011Applicant: Solvay Solexis S.p.A.Inventors: Giovanni Boccaletti, Fabio Riganti, Manfred Jungk
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Publication number: 20100280280Abstract: 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: ApplicationFiled: April 30, 2009Publication date: November 4, 2010Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: Sheng Peng, Sourav K. Sengupta
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Publication number: 20100280281Abstract: 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: ApplicationFiled: April 30, 2009Publication date: November 4, 2010Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: Karl Jeffrey Sweetman, Scott Andrew Backer
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Publication number: 20100240930Abstract: 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: ApplicationFiled: October 3, 2008Publication date: September 23, 2010Applicant: SOLVAY SOLEXIS S.P.A.Inventors: Claudio Tonelli, Graziano Giuseppe Vezzulli, Rosaldo Picozzi, Piero Gavezotti, Antonella DI Meo
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Patent number: 7795375Abstract: It is to provide a compound which has a low vapor pressure and low viscosity, which is less problematic in deterioration during its use and which is useful as e.g. a lubricant, a surface modifier or a surfactant. A fluoropolyether compound represented by the formula (X—)xY(—Z)z, wherein X is a group represented by the formula HO—(CH2CH2O)a.(CH2CH(OH)CH2O)b—(CH2)c—CF2O(CF2CF2O)d— (wherein “a” is an integer of from 0 to 100, b is an integer of from 0 to 100, c is an integer of from 1 to 100, and d is an integer of from 1 to 200), Z is a group represented by the formula RFO(CF2CF2O)g— (wherein RF is e.g. a C1-20 perfluoroalkyl group having an etheric oxygen atom inserted between carbon-carbon atoms, and g is an integer of from 3 to 200), Y is e.g. a (x+z) valent perfluorinated saturated hydrocarbon group, x is an integer of at least 2, z is an integer of at least 0, and (x+z) is an integer of from 3 to 20.Type: GrantFiled: July 11, 2006Date of Patent: September 14, 2010Assignee: Asahi Glass Company, LimitedInventors: Daisuke Shirakawa, Kazuya Oharu, Takashi Okazoe
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Patent number: 7772443Abstract: An iodine-containing fluoropolyether represented by the following general formula [I]: RfO[CF(CF3)CF2O]mCF(CF3)(CH2)nI??[I] (where Rf is a perfluoroalkyl group having 1-3 carbon atoms, m is an integer of 0-10, and n is an integer of 3-12), is a novel compound having a perfluoropolyetheralkyl group capable of giving a flexibility to the molecule chain through the etheral bond, said perfluoropolyether alkyl group being bonded to the alkyl iodide having an alkyl group having 3 or more carbon atoms, and can be produced by reaction of a fluoropolyether group-containing alcohol represented by the following general formula [II]: RfO[CF(CF3)CF2O]mCF(CF3)(CH2)nOH??[II] (Where Rf, m, and n have the same meanings as defined above) with a metal iodide, preferably potassium iodide.Type: GrantFiled: May 22, 2006Date of Patent: August 10, 2010Assignee: Unimatec Co., Ltd.Inventors: Keisuke Kokin, Kimihiko Urata, Takehiro Sonoi
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Publication number: 20100028721Abstract: A lubricant for magnetic disks which can form a lubricating layer having a reduced thickness while attaining a high coverage and is excellent in heat resistance and adhesion to a protective layer. The lubricant for magnetic disks comprises a perfluoropolyether compound in which the relationship between the number-average molecular weight and the standardized value of the number of hydroxy groups contained in the molecule satisfies the following: the number-average molecular weight is in the range of 1,000-6,000; the standardized value of the number of hydroxy groups contained in the molecule is 180 or higher; and the compound is in a region located below the line connecting the point where the number-average molecular weight is 1,000 and the standardized value of the number of hydroxy groups in the molecule is 400 to the point where the number-average molecular weight is 6,000 and the standardized value of the number of hydroxy groups in the molecule is 1,600.Type: ApplicationFiled: September 28, 2007Publication date: February 4, 2010Applicant: HOYA CORPORATIONInventors: Katsushi Hamakubo, Koichi Shimokawa, Kota Suzuki
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Publication number: 20090291212Abstract: Highly volatile MOCVD (Metal-Organic Chemical Vapor Deposition) precursors are disclosed comprising a complex between a fluoroalkoxide ligand and one or more alkali, alkaline earth, lanthanoids or yttrium metals and one or more donor molecules. In one example, the fluoroalkoxide ligand is perfluoro-tert-butoxide and the complex is a heterobimetallic complex. These MOCVD precursors are highly volatile, non-oligomeric, non-pyrophoric and can be synthesized with high yields. They are ideally suited for MOCVD applications because of their ability to vaporize at low temperatures and at atmospheric pressure thus enabling the deposition of a more uniform and homogeneous metal coating of known stoichiometry on to a substrate.Type: ApplicationFiled: May 26, 2009Publication date: November 26, 2009Applicant: Syracuse UniversityInventors: William D. Buchanan, Karin Ruhlandt-Senge
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Publication number: 20090247786Abstract: A benzyl vinyl ether represented by the following formula is hydrolyzed in the presence of a catalyst selected among Arrhenius acids and Lewis acids to obtain 3,3,3-trifluoropropionaldehyde. Subsequently, the 3,3,3-trifluoropropionaldehyde is oxidized with an oxidizing agent. Thus, 3,3,3-trifluoropropionic acid can be more advantageously produced than in conventional techniques from an inexpensive starting material.Type: ApplicationFiled: October 24, 2006Publication date: October 1, 2009Applicant: Central Glass Company, LimitedInventors: Takeo Komata, Kenji Hosoi, Shinya Akiba
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Publication number: 20090247791Abstract: The present invention refers to a process for the preparation of fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ether (sevoflurane) which includes a step that consists of reacting hexafluoroisopropanol with a formaldehyde equivalent selected among paraformaldehyde or 1,3,5-trioxane, a chlorinating agent selected from the group consisting of oxalyl chloride, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, sulfuryl chloride and thionyl chloride, and a strong acid selected from the group consisting of concentrated or fuming sulfuric acid resulting in the formation of the intermediate sevochlorane which is converted to sevoflurane in a second step which consists of reacting sevochlorane with an alkali metal fluoride, or a linear or branched chain tetra-alkyl quarternary ammonium fluoride in the presence of a sub-stoichiometric quantity of an alkali metal iodide, or a linear or branched alkyl chain tetra-alkyl quarternary ammonium iodide, preferably in a solvent.Type: ApplicationFiled: September 29, 2006Publication date: October 1, 2009Applicant: CRISTÁLIA PRODUTOS QUÍMICOS FARMACÊUTICOS LTDAInventors: Ogari Pacheco, Antonio Carlos Teixeira, Edson Luiz Lima, Maria Alice Böckelmann
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Publication number: 20090171127Abstract: A novel fluorine-containing ether alcohol having a terminal perfluoromethoxy group represented by the following general formula: CF3O[CF(CF3)CF2O]nCF(CF3)CH2OH (where n is an integer of 0-12) can be produced by reduction reaction of a fluorine-containing ether carboxylic acid alkyl ester represented by the following general formula: CF3O[CF(CF3)CF2O]nCF(CF3)COOR (where R is an alkyl group, and n is an integer of 0-12), and the fluorine-containing ether alcohol alone or as a mixture with a fluorine-containing ether alcohol having a terminal perfluoroethoxy group or a terminal perfluoropropoxy group is expected to show a peculiar surfactant characteristic owing to the peculiarity of reaction at the terminal position, and can be used as a dispersing agent or a levelling agent.Type: ApplicationFiled: January 12, 2007Publication date: July 2, 2009Applicant: UNIMATEC CO. LTD.Inventors: Seiichiro Murata, Keisuke Kokin, Takehiro Sonoi
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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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Publication number: 20090118550Abstract: A process for preparing monocarboxylic perfluoropolyethers of formula: A-O-(RF)z-(CFY)t-C(O)OX (I) wherein: X is H, C1-C10 alkyl, or an aryl group; Y=F, CF3; t=1, 2 or 3; A is a C1-C4 perfluoroalkyl end group; z=0 or 1; RF is a perfluorooxyalkylene chain; having a number average molecular weight in the range 180-8,000; comprising the following steps: a) one or more distillations of perfluoropolyethers (PFPE) of formula T-O-(RF)z-T? (II) wherein: z and RF are as above defined; T, T?, equal to or different from each other, are selected from acyl fluoride or carbonyl-containing functional end groups and non functional end groups to obtain one PFPE fraction of formula (II) wherein the difference between the minimum and the maximum molecular weight of the components is lower than or equal to 600; b) partial fluorination of the fraction obtained in a); c) esterification c1) and/or hydrolysis c2) of the mixture obtained in b); d) distillation of the product obtained in c2) or in c1).Type: ApplicationFiled: April 3, 2007Publication date: May 7, 2009Applicant: Solvay Solexis S.p.A.Inventors: Giuseppe Marchionni, Ugo De Patto, Pier Antonio Guarda
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Publication number: 20090048469Abstract: An iodine-containing fluoropolyether represented by the following general formula [I]: RfO[CF(CF3)CF2O]mCF(CF3)(CH2)nI??[I] (where Rf is a perfluoroalkyl group having 1-3 carbon atoms, m is an integer of 0-10, and n is an integer of 3-12), is a novel compound having a perfluoropolyetheralkyl group capable of giving a flexibility to the molecule chain through the etheral bond, said perfluoropolyether alkyl group being bonded to the alkyl iodide having an alkyl group having 3 or more carbon atoms, and can be produced by reaction of a fluoropolyether group-containing alcohol represented by the following general formula [II]: RfO[CF(CF3)CF2O]mCF(CF3)(CH2)nOH??[II] (Where Rf, m, avd n have the same meanings as defined above) with a metal iodide, preferably potassium iodide.Type: ApplicationFiled: May 22, 2006Publication date: February 19, 2009Inventors: Keisuke Kokin, Kimihiko Urata, Takehiro Sonoi
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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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Publication number: 20080245509Abstract: The present invention provides an apparatus comprising a device and a mechanism for heat transfer comprising a hydrofluoroether heat-transfer fluid wherein the heat transfer fluid is represented by the following structure: Rf—O—Rh—O—Rf? wherein O is oxygen; Rf and Rf? are, independently, a fluoroaliphatic group, wherein each Rf and Rf? contain 1 hydrogen atom; Rh is independently a linear, branched or cyclic alkylene group having from 2 to about 8 carbon atoms and at least 4 hydrogen atoms, and wherein the hydrofluoroether compound is free of —O—CH2—O—. Another embodiment of the present invention is a method therefor.Type: ApplicationFiled: May 13, 2008Publication date: October 9, 2008Inventors: Michael G. Costello, Richard M. Flynn, Frederick E. Behr
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Publication number: 20080194881Abstract: Peroxidic perfluoropolyethers having formula: X1—O(CF2O)n1(CF2CF2O)m1(CF2(CF2)zCF2O)p1(O)h—X2 ??(I) wherein: X1 and X2, equal to or different from each other, are chain end groups selected among —CF2COF, —COF, —SO2F; n1, m1, p1 and h are integers such that the number average molecular weight is in the range 700-100,000; z=1 or 2; with the proviso that: the m1/n1 ratio is between 0.2 and 10; the p1/(n1+m1) ratio is lower than 0.05; the h/(n1+m1+p1) ratio is such that the PO content, defined as grams of active oxygen/100 g of compound, is in the range 0.8-4.5, preferably 1.4-3.8; the perfluorooxyalkylene units being statistically distributed along the polymeric chain.Type: ApplicationFiled: April 8, 2008Publication date: August 14, 2008Applicant: Solvay Solexis S.p.A.Inventors: Giuseppe MARCHIONNI, Pier Antonio Guarda
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Patent number: 7388646Abstract: Use in optical systems as liquids to transmit light at wave lengths lower than 250 nm, in particular at 157 nm, of perfluoropolyethers having the following formula: X1—O(CF2O)n(CF2CF2O)m(CF2CF2CF2O)p(CF2CF2CF2CF2O)q—X2??(I) wherein: the repeating units —CF2O—, —CF2CF2O—, —CF2CF2CF2O—, —CF2CF2CF2CF2O— are statistically distributed along the chain; —X1 and —X2 are perfluoroalkyl chain end groups equal to or different from each other, having formula —(CF2)zCF3 wherein z is 0 or an integer from 1 to 3; n, m, p, q are 0 or integers comprised between 1 and 100, with the proviso that: at least one among n, m, p and q is different from zero; the ratio between the oxygen atoms and the carbon atoms (O/C) is higher than 0.33; wherein the chlorine atoms, determined by 19F-NMR are substantially absent.Type: GrantFiled: September 30, 2004Date of Patent: June 17, 2008Assignee: Solvay Solexis S.p.A.Inventors: Mattia Bassi, Pier Antonio Guarda
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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: 7319173Abstract: A process for preparing (per)fluorohalogenethers having general formula: wherein: A and A?, equal to our different from each other, are selected among Cl, Br, H; m=1, 2; n=0, 1; R1 is a fluorinated substituent, preferably perfluorinated, selected from the following groups: C1-C20 linear or branched alkylic; C3-C7 cycloalkylic; aromatic, C6-C10 arylalkyl; heterocyclic or C5-C10-alkylheterocyclic; preferably perfluoroalkyl; R? is as defined in the application; by reaction of carbonyl compounds having formula: wherein: R1 and n are as above; u=0, 1; R? is as defined in the application; in liquid phase, with elemental fluorine and with olefinic compounds of formula: CAF?CA?F2??(III) wherein A and A? are as above, at temperatures from ?120° C. to ?20° C., preferably from ?100° C. to ?40° C., optionally in the presence of an inert solvent under the reaction conditions.Type: GrantFiled: January 28, 2005Date of Patent: January 15, 2008Assignee: Solvay Solexis S.p.A.Inventors: Vito Tortelli, Stefano Millefanti, Pierangelo Calini
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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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Publication number: 20070224452Abstract: A lubricant is provided that can form a sufficiently thin one-molecule film surface even when it is highly polymerized. When used for a magnetic recording medium lubricant layer and/or a head slider lubricant layer of a magnetic recording device, it can make the film thickness of the lubricant layers very small, with the result that it can furnish an increased reliability to the magnetic recording device in a wide temperature-range environment without damaging the flying stability. This lubricant comprises a fluorine-containing polymer having a specific structure. Such a fluorine-containing polymer can be manufactured by reacting a compound having a specific structure and 1,3-butadiene diepoxide.Type: ApplicationFiled: September 5, 2006Publication date: September 27, 2007Applicant: FUJITSU LIMITEDInventors: Masaaki Sasa, Hiroshi Chiba