Fluorine Patents (Class 568/677)
  • Patent number: 9145471
    Abstract: 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: Grant
    Filed: October 23, 2012
    Date of Patent: September 29, 2015
    Assignee: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.
    Inventors: Claudio Adolfo Pietro Tonelli, Roberto Valsecchi, Fabrizio Mutta
  • Publication number: 20150148565
    Abstract: 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: Application
    Filed: February 3, 2015
    Publication date: May 28, 2015
    Inventor: Thomas Joseph Martin
  • Publication number: 20150112095
    Abstract: 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: Application
    Filed: October 17, 2013
    Publication date: April 23, 2015
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventor: ROMAN B. LARICHEV
  • Patent number: 8865947
    Abstract: 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: Grant
    Filed: December 6, 2012
    Date of Patent: October 21, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Kenneth Gene Moloy, Sheng Peng
  • Publication number: 20140287240
    Abstract: 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: Application
    Filed: June 6, 2014
    Publication date: September 25, 2014
    Applicant: ASAHI GLASS COMPANY, LIMITED
    Inventors: Eisuke MUROTANI, Taiki Hoshino, Akira Isobe, Daisuke Shirakawa, Daisuke Jomuta, Nobuyuki Otozawa
  • Publication number: 20140275635
    Abstract: 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: Application
    Filed: October 23, 2012
    Publication date: September 18, 2014
    Inventors: Claudio Adolfo Pietro Tonelli, Roberto Valsecchi, Fabrizio Mutta
  • Publication number: 20130317257
    Abstract: 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: Application
    Filed: July 30, 2013
    Publication date: November 28, 2013
    Applicant: HGST Netherlands B.V.
    Inventors: John M. Burns, Hong Deng, Xing-Cai Guo, Bruno Marchon, Daryl J. Pocker, Robert Waltman
  • Publication number: 20130256588
    Abstract: 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: Application
    Filed: December 16, 2011
    Publication date: October 3, 2013
    Applicant: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.
    Inventors: Vito Tortelli, Marco Galimberti, Cristiano Monzani, Piero Gavezotti
  • Patent number: 8513471
    Abstract: 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: Grant
    Filed: October 3, 2008
    Date of Patent: August 20, 2013
    Assignee: Solvay Solexis S.p.A.
    Inventors: Claudio Tonelli, Graziano Giuseppe Vezzulli, Rosaldo Picozzi, Piero Gavezotti, Antonella Di Meo
  • 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: 8350094
    Abstract: 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: Grant
    Filed: June 27, 2011
    Date of Patent: January 8, 2013
    Assignee: 3M Innovative Properties Company
    Inventors: Richard M. Flynn, Michael J. Bulinski, Michael G. Costello
  • Publication number: 20120315504
    Abstract: 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: Application
    Filed: June 4, 2012
    Publication date: December 13, 2012
    Inventors: Tsuyoshi SHIMIZU, Nagayoshi KOBAYASHI
  • Publication number: 20120298333
    Abstract: 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: Application
    Filed: August 13, 2012
    Publication date: November 29, 2012
    Inventors: Richard M. Flynn, Michael G. Costello, Michael J. Bulinski
  • Patent number: 8217119
    Abstract: 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: Grant
    Filed: November 26, 2007
    Date of Patent: July 10, 2012
    Assignee: Solvay Solexis S.p.A.
    Inventors: Julio A. Abusleme, Marco Avataneo, Giancarlo Perfetti
  • Publication number: 20120127601
    Abstract: 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: Application
    Filed: March 27, 2010
    Publication date: May 24, 2012
    Applicant: WD MEDIA (SINGAPORE) PTE. LTD.
    Inventors: Kota Suzuki, Koichi Shimokawa, Katsushi Hamakubo, Kae Itoh
  • Patent number: 8178480
    Abstract: 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: Grant
    Filed: September 28, 2007
    Date of Patent: May 15, 2012
    Assignee: WD Media (Singapore) Pte. Ltd.
    Inventors: Katsushi Hamakubo, Koichi Shimokawa, Kota Suzuki
  • Publication number: 20120059144
    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: Application
    Filed: May 6, 2010
    Publication date: March 8, 2012
    Applicant: SOLVAY SOLEXIS S.P.A.
    Inventors: Claudio Adolfo Pietro Tonelli, Graziano Giuseppe Vezzulli, Rosaldo Picozzi, Piero Gavezotti
  • Publication number: 20120040189
    Abstract: 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: Application
    Filed: October 21, 2011
    Publication date: February 16, 2012
    Applicant: Asahi Glass Company, Limited
    Inventors: Daisuke Shirakawa, Yoshiyuki Gozu, Taiki Hoshino
  • Patent number: 8071816
    Abstract: 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 indepe
    Type: Grant
    Filed: June 30, 2008
    Date of Patent: December 6, 2011
    Assignee: 3M Innovative Properties Company
    Inventors: Richard M. Flynn, Michael G. Costello
  • Patent number: 8058481
    Abstract: 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: Grant
    Filed: April 30, 2009
    Date of Patent: November 15, 2011
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Kenneth Gene Moloy, James A. Schultz
  • Patent number: 8053606
    Abstract: 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: Grant
    Filed: April 30, 2009
    Date of Patent: November 8, 2011
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Karl Jeffrey Sweetman, Scott Andrew Backer
  • Patent number: 8039677
    Abstract: 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: Grant
    Filed: April 30, 2009
    Date of Patent: October 18, 2011
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Sheng Peng, Sourav Kumar Sengupta
  • Publication number: 20110213113
    Abstract: RF-compositions including surfactants, foam stabilizers, monomers, polymers, urethanes, intermediates, metal complexes, phosphate esters as well as telomerization methods are provided.
    Type: Application
    Filed: May 6, 2011
    Publication date: September 1, 2011
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY CHEMTURA CORPORATION
    Inventors: Andrew Jackson, Vimal Sharma, E. Bradley Edwards, Janet Boggs, Vicki Hedrick, Stephan Brandstadter, John Chien, Edward Norman, Robert Kaufman, Bruno Ameduri, George K. Kostov
  • Patent number: 7988877
    Abstract: 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: Grant
    Filed: November 3, 2008
    Date of Patent: August 2, 2011
    Assignee: 3M Innovative Properties Company
    Inventors: Richard M. Flynn, Michael J. Bulinski, Michael G. Costello
  • Publication number: 20110165037
    Abstract: 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: Application
    Filed: January 7, 2011
    Publication date: July 7, 2011
    Inventors: Rustem F. Ismagilov, Jason Eugene Kreutz
  • Patent number: 7964552
    Abstract: 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: Grant
    Filed: November 13, 2007
    Date of Patent: June 21, 2011
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Axel Hans-Joachim Herzog, Shaun Raymond Rinehimer
  • Patent number: 7956023
    Abstract: 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: Grant
    Filed: January 24, 2007
    Date of Patent: June 7, 2011
    Assignee: Asahi Glass Company, Limited
    Inventors: Daisuke Shirakawa, Hidekazu Okamoto
  • Publication number: 20110067957
    Abstract: 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: Application
    Filed: May 15, 2009
    Publication date: March 24, 2011
    Applicant: Solvay Solexis S.p.A.
    Inventors: Giovanni Boccaletti, Fabio Riganti, Manfred Jungk
  • Publication number: 20100280280
    Abstract: 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: Application
    Filed: April 30, 2009
    Publication date: November 4, 2010
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Sheng Peng, Sourav K. Sengupta
  • Publication number: 20100280281
    Abstract: 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: Application
    Filed: April 30, 2009
    Publication date: November 4, 2010
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Karl Jeffrey Sweetman, Scott Andrew Backer
  • Publication number: 20100240930
    Abstract: 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: Application
    Filed: October 3, 2008
    Publication date: September 23, 2010
    Applicant: SOLVAY SOLEXIS S.P.A.
    Inventors: Claudio Tonelli, Graziano Giuseppe Vezzulli, Rosaldo Picozzi, Piero Gavezotti, Antonella DI Meo
  • Patent number: 7795375
    Abstract: 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: Grant
    Filed: July 11, 2006
    Date of Patent: September 14, 2010
    Assignee: Asahi Glass Company, Limited
    Inventors: Daisuke Shirakawa, Kazuya Oharu, Takashi Okazoe
  • Patent number: 7772443
    Abstract: 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: Grant
    Filed: May 22, 2006
    Date of Patent: August 10, 2010
    Assignee: Unimatec Co., Ltd.
    Inventors: Keisuke Kokin, Kimihiko Urata, Takehiro Sonoi
  • Publication number: 20100028721
    Abstract: 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: Application
    Filed: September 28, 2007
    Publication date: February 4, 2010
    Applicant: HOYA CORPORATION
    Inventors: Katsushi Hamakubo, Koichi Shimokawa, Kota Suzuki
  • Publication number: 20090291212
    Abstract: 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: Application
    Filed: May 26, 2009
    Publication date: November 26, 2009
    Applicant: Syracuse University
    Inventors: William D. Buchanan, Karin Ruhlandt-Senge
  • Publication number: 20090247791
    Abstract: 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: Application
    Filed: September 29, 2006
    Publication date: October 1, 2009
    Applicant: CRISTÁLIA PRODUTOS QUÍMICOS FARMACÊUTICOS LTDA
    Inventors: Ogari Pacheco, Antonio Carlos Teixeira, Edson Luiz Lima, Maria Alice Böckelmann
  • Publication number: 20090247786
    Abstract: 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: Application
    Filed: October 24, 2006
    Publication date: October 1, 2009
    Applicant: Central Glass Company, Limited
    Inventors: Takeo Komata, Kenji Hosoi, Shinya Akiba
  • Publication number: 20090171127
    Abstract: 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: Application
    Filed: January 12, 2007
    Publication date: July 2, 2009
    Applicant: UNIMATEC CO. LTD.
    Inventors: Seiichiro Murata, Keisuke Kokin, Takehiro Sonoi
  • Patent number: 7534845
    Abstract: 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: Grant
    Filed: December 18, 2006
    Date of Patent: May 19, 2009
    Assignee: Solvay Solexis S.p.A.
    Inventor: Walter Navarrini
  • Publication number: 20090118550
    Abstract: 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: Application
    Filed: April 3, 2007
    Publication date: May 7, 2009
    Applicant: Solvay Solexis S.p.A.
    Inventors: Giuseppe Marchionni, Ugo De Patto, Pier Antonio Guarda
  • Publication number: 20090048469
    Abstract: 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: Application
    Filed: May 22, 2006
    Publication date: February 19, 2009
    Inventors: Keisuke Kokin, Kimihiko Urata, Takehiro Sonoi
  • Patent number: 7488852
    Abstract: 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: Grant
    Filed: July 28, 2006
    Date of Patent: February 10, 2009
    Assignee: Ausimont S.p.A.
    Inventors: Giuseppe Marchionni, Mario Visca
  • Publication number: 20080245509
    Abstract: 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: Application
    Filed: May 13, 2008
    Publication date: October 9, 2008
    Inventors: Michael G. Costello, Richard M. Flynn, Frederick E. Behr
  • Publication number: 20080194881
    Abstract: 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: Application
    Filed: April 8, 2008
    Publication date: August 14, 2008
    Applicant: Solvay Solexis S.p.A.
    Inventors: Giuseppe MARCHIONNI, Pier Antonio Guarda
  • Patent number: 7388646
    Abstract: 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: Grant
    Filed: September 30, 2004
    Date of Patent: June 17, 2008
    Assignee: Solvay Solexis S.p.A.
    Inventors: Mattia Bassi, Pier Antonio Guarda
  • Patent number: 7388114
    Abstract: 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: Grant
    Filed: May 1, 2007
    Date of Patent: June 17, 2008
    Assignee: Asahi Glass Company, Limited
    Inventors: Daisuke Shirakawa, Takashi Okazoe, Kazuya Oharu, Shu-zhong Wang, Koichi Murata, Kengo Kawahara
  • Patent number: 7319173
    Abstract: 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: Grant
    Filed: January 28, 2005
    Date of Patent: January 15, 2008
    Assignee: Solvay Solexis S.p.A.
    Inventors: Vito Tortelli, Stefano Millefanti, Pierangelo Calini
  • Patent number: 7288682
    Abstract: 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: Grant
    Filed: July 8, 2005
    Date of Patent: October 30, 2007
    Assignee: Solvay Solexis S.p.A.
    Inventors: Alexandre Tchistiakov, Simonetta Fontana, Claudio Tonelli
  • Publication number: 20070224452
    Abstract: 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: Application
    Filed: September 5, 2006
    Publication date: September 27, 2007
    Applicant: FUJITSU LIMITED
    Inventors: Masaaki Sasa, Hiroshi Chiba
  • Patent number: 7230140
    Abstract: 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: Grant
    Filed: April 18, 2005
    Date of Patent: June 12, 2007
    Assignee: Asahi Glass Company, Limited
    Inventors: Daisuke Shirakawa, Takashi Okazoe, Kazuya Oharu, Shu-zhong Wang, Koichi Murata, Kengo Kawahara