Fluorine Patents (Class 568/615)
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Patent number: 6255535Abstract: The present invention describes a novel process for the preparation of perfluoro allyl ethers. The process involves providing a hydrogen-containing precursor comprising at least one 1,2-dichloro alkyl ether moiety, fluorinating the precursor to provide a perfluorinated intermediate, and dechlorinating the perfluorinated intermediate to the corresponding perfluorinated ether. A reaction product of a perfluorinated olefin and an allyl ether may also be used as a precursor. Such a reaction product is chlorinated before the fluorination step. Perfluoro vinyl or allyl ethers may be used in place of the perfluorinated olefin. Novel perfluoro alkoxy compounds are also described.Type: GrantFiled: December 22, 1999Date of Patent: July 3, 2001Assignees: Dyneon LLC, 3M Innovative Properties CompanyInventors: Jay F. Schulz, George G. I. Moore, Werner Schwertfeger, Klaus Hintzer, Zai-Ming Qiu, Miguel A. Guerra, Erik D. Hare, Allan T. Worm
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Patent number: 6255536Abstract: The present invention describes a novel process for the preparation of perfluorovinyl ethers. The process involves providing a hydrocarbon precursor that may be partially halogenated, fluorinating the precursor to provide a perfluorinated intermediate, and converting the perfluorinated intermediate to the desired perfluorinated ether. Novel perfluorovinyl ethers are also provided.Type: GrantFiled: December 22, 1999Date of Patent: July 3, 2001Assignees: Dyneon LLC, 3M Innovative Properties CompanyInventors: Allan T. Worm, George G. I. Moore, Miguel A. Guerra, Werner Schwertfeger, Klaus Hintzer, Zai-Ming Qiu, Erik D. Hare
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Patent number: 6248889Abstract: A process for preparing a fluoride from its corresponding alcohol comprises the steps of (a) forming a mixture comprising (i) at least one fluorinated, saturated aliphatic or alicyclic sulfonyl fluoride (for example, perfluorobutanesulfonyl fluoride) and (ii) at least one primary or secondary alcohol; and (b) adding a molar excess of at least one strong, aprotic, non-nucleophilic, hindered, double bond-containing, organic base (for example, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)) to the mixture.Type: GrantFiled: November 20, 1998Date of Patent: June 19, 2001Assignee: 3M Innovative Properties CompanyInventors: Patricia M. Savu, Daniel C. Snustad
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Patent number: 6211415Abstract: A hexafluoropropylene oxide oligomer of the formula: RfO[CF(CF3)CF2O]nCF(CF3)COF in which Rf is a group represented by the formula: F(CF2)m— in which m is an integer of 1 to 8, or the formula: (CF3)2CF(CF2)q— in which q is an integer of 0 to 6, and n is a number of 3 to 20 is heated and thermally decomposed in a solvent at a temperature of at least 100° C. in the presence of a compound which generates a fluoride (F−) ion to obtain mainly the dimer, trimer and tetramer of hexafluoropropylene oxide. Thus, the valuable low molecular weight oligomers of hexafluoropropylene oxide can be obtained from high molecular weight oligomers of hexafluoropropylene oxide which have been discarded.Type: GrantFiled: May 21, 1999Date of Patent: April 3, 2001Assignee: Daikin Industries, Ltd.Inventors: Shigeru Morita, Toshihiko Amano
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Patent number: 6191314Abstract: A process for obtaining (per) fluoropolyethers substituted at one or at both end groups with a halogen atom selected from bromine or iodine, having the formula: A—CF2—O—(CF2CF2O)p—(CF2O)q—CF2—B (III) wherein A=B=halogen; or A=halogen and B=COOH or F, and the halogen is I or Br; p and q are integers such as to give a number average molecular weight (MW) in the range 350-5000 and the ratio p/q=0.5-2.0. The process includes treating di- or poly-acylperoxides having an average equivalent weight in the range 350-5000, of formula: T—CF2—O—[(CF2CF2O)p—(CF2O)q—CF2—CO—O—O——CO—CF2—(OCF2)q—(OCF2CF2)p]y—OCF2—COOH (II) with a halogen selected from iodine or bromine, in a polyhalogenated organic solvent, at temperatures between 20° and 80° C.Type: GrantFiled: June 9, 1999Date of Patent: February 20, 2001Assignee: Ausimont S.p.A.Inventors: Ivan Wlassics, Vito Tortelli
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Patent number: 6150565Abstract: A process is disclosed for making diiodofluorinated compounds of the formula ICF.sub.2 (A).sub.n I wherein n is an integer of at least 1 and each A is CXYCQZ wherein each X, Y, Q, and Z are each independently selected from the group consisting of H, F, Cl, R.sub.F and OR.sub.F, and R.sub.F is a perfluoroalkyl group or perfluorinated polyether group wherein one or more of the fluorines is optionally replaced by a substituent selected from the group consisting of chlorine, bromine, iodine, hydrogen, sulfonyl fluoride, nitrile, ester, acyl chloride and acyl fluoride. The process involves reacting an olefin of the formula CXY.dbd.CQZ with CF.sub.2 I.sub.2 at a temperature in the range of from about 120.degree. C. to 240.degree. C.Diiodofluorinated compounds of the formula ICF.sub.2 CH.sub.2 CHR.sub.F I are also disclosed.Type: GrantFiled: September 8, 1998Date of Patent: November 21, 2000Assignee: E. I. du Pont de Nemours and CompanyInventor: Zhen-Yu Yang
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Patent number: 6127498Abstract: Hydrogenated fluoromodified polymers obtainable by reaction among hydrogenated polymers and the modifier having a polyether structure:RfO(CF.sub.2 CF.sub.2 O).sub.m (CF.sub.2 O).sub.n --CF.sub.2 --A.sub.q --T.sub.p (I)wherein A is a linking bridge bound to the end group --CF.sub.2 -- of the perfluoropolyether chain, T represents one or more reactive functional groups; p and q are integers, p ranges from 1 to 4, q is an integer from 0 to 1; m and n are integers such that m/n is comprised between 0.2 and 5, Rf is a perfluoroalkyl from 1 to 3 carbon atoms.Type: GrantFiled: April 6, 1998Date of Patent: October 3, 2000Assignee: Ausimont S.p.A.Inventors: Claudio Tonelli, Giovanni Simeone, Tania Trombetta
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Patent number: 6093495Abstract: A water or aqueous soluble salt of a perfluoro polyether alcohol is applied to form a lubricant topcoat on a magnetic recording medium. Suitable soluble salts include the sodium salt of a perfluoro polyether diol.Type: GrantFiled: October 29, 1997Date of Patent: July 25, 2000Assignee: Seagate Technology, Inc.Inventor: Samuel J. Falcone
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Patent number: 6034207Abstract: A hexafluoropropene oxide polymer of formula (1) having a dispersity Mw/mn of up to 1.10 is useful as a raw material for liquid rubber. In formula (1), R is --COF, --I, --Br, --CH.sub.2 OH, --CH.sub.2 OCH.sub.2 CH.dbd.CH.sub.2, --COOR.sup.1 or --CONR.sup.2 R.sup.3 wherein R.sup.1, R.sup.2 and R.sup.3 are independently hydrogen or monovalent C.sub.1-20 hydrocarbon groups which may contain N, O, Si or S, or R.sup.2 and R.sup.3 form a ring with the N atom, Rf is a C.sub.1-6 perfluoroalkylene group or a C.sub.2-10 perfluorooxyalkylene group, and x+y=30 to 400.Type: GrantFiled: April 1, 1999Date of Patent: March 7, 2000Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Noriyuki Koike, Takashi Matsuda, Shinichi Sato
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Patent number: 6019909Abstract: A novel fluorinated hydrocarbon compound containing an oxygen or sulfur atom in its molecule, produced by the nucleophilic reaction of a fluorine compound with a hydrocarbon compound. This compound is useful as a lubricant for various applications and particularly excellent as an oil for refrigerators wherein hydrochlorofluorocarbon is used as the refrigerant and as a magnetic recording medium lubricant.Type: GrantFiled: July 21, 1995Date of Patent: February 1, 2000Assignee: Daikin Industries, Ltd.Inventors: Satoshi Ide, Katsuki Fujiwara, Masayuki Yamana, Yoshitaka Honda, Ikuo Yamamoto, Fumihiko Yamaguchi, Eiji Seki, Tatsuya Otsuka, Satoshi Ishida
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Patent number: 6002048Abstract: A novel fluorine-containing compound having functions corresponding to those of fluorine is provided, which is stable under various conditions, excellent in compatibility with other solvents, and can be widely utilized as solvents, cosmetics, detergents, emulsifiers, surface finishing agents, lubricants, as well as lubricants or oils in the field of semiconductor/electronics.That is, the present invention provides fluorine-containing ether compounds represented by the general formula (1):Rf--(CH.sub.2).sub.n --O--R.sup.1 ( 1)(wherein, Rf represents a straight or branched C.sub.1-20 perfluoroalkyl group, R.sup.1 represents a straight or branched C.sub.11-20 alkyl group, n is a number from 1 to 8) and gelling agent containing the same.Type: GrantFiled: April 9, 1998Date of Patent: December 14, 1999Assignee: Kao CorporationInventors: Yasuyuki Fujii, Eiko Tamura, Shinji Yano, Hisakazu Furugaki
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Patent number: 5969192Abstract: A process for preparing hydrogen-terminated polyoxyperfluoroalkanes having molecular weight lower than 1800, by decarboxylation of the corresponding polyoxyperfluoroalkanes having one or two end groups selected form --OCF.sub.2 COOZ, --OCF.sub.2 CF.sub.2 COOZ and --OCF(CF.sub.3)COOZ, wherein Z is an alkaline metal or ammonium, carried out in the presence of water at temperatures from 140.degree.-170.degree. C. and under a pressure of at least 4 atmospheres.Type: GrantFiled: December 19, 1996Date of Patent: October 19, 1999Assignee: Ausimont S.p.A.Inventors: Giuseppe Marchionni, Gianfranco Spataro, Ezio Strepparola
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Patent number: 5959058Abstract: Use of fluorinated polymers based on fluoropolyethers for the preparation of crosslinkable high dry formulations comprising a fluorinated part R.sub.F and optionally an hydrogenated part R.sub.H, not containing groups capable of linking by means of hydrogen bonds to basic acceptors, an hydrogenated part Rh.sub.1 and Rh.sub.2, wherein Rh.sub.1 is equal to or different from Rh.sub.2, and Rh.sub.1 and/or Rh.sub.2 being linking bonds containing at least a functional group capable of linking by means of hydrogen bonds with basic acceptors, the bonds joining the fluorinated part to the hydrogenated part being of ether C--O simple type, the terminals T'.sub.a and T" being such as to render the structure mono-, bi- or polyfunctional, and subsequent crosslinking of the fluorinated polymer, the monofunctional products being always in admixture with a resin having even a higher functionality than the described type; the preferred fluorinated products have the formula:T"--(Rh.sub.2).sub.y (R.sub.H).sub.x --R.sub.F --(R.Type: GrantFiled: March 11, 1996Date of Patent: September 28, 1999Assignee: Ausimont S.p.A.Inventors: Claudio Tonelli, Massimo Scicchitano, Stefano Turri
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Patent number: 5948737Abstract: Greases comprising a mineral and/or synthetic lubricating oil having an hydrogenated basis, a fluoropolyethereal oil and an organic or inorganic thickening agent, wherein the weight ratio lubricating oil+fluoropolyethereal oil/thickening agent ranges from 97:3 to 80:20 and the weight ratio lubricating oil/fluoropolyethereal oil ranges from 95:5 to 60:40.Type: GrantFiled: November 18, 1996Date of Patent: September 7, 1999Assignee: Ausimont S.p.A.Inventors: Padmanabhan Srinivasan, Laura Montagna, Paolo Savelli, Costante Corti
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Patent number: 5928557Abstract: A poly-.alpha.-olefin:fluoroalkene diblock polymer useful as a lubricant and having a linking moiety of a heteroatom or a heteroatom-containing group linking a poly-.alpha.-olefin oligomeric unit with a fluoroalkene oligomeric unit and being miscible in hydrofluorocarbons or a mixture of hydrofluorocarbons, hydrochlorofluorocarbons, chlorofluorocarbons and the miscible composition useful as compressor fluids.Type: GrantFiled: April 9, 1992Date of Patent: July 27, 1999Assignee: Minnesota Mining and Manufacturing CompanyInventors: James Frederick Sanders, William Mario Lamanna
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Patent number: 5917008Abstract: Polytetrafluoroethylene (PTFE) dispersions in an organic solvent, comprising:(A) from 2 to 40% by weight of PTFE in powder form;(B) from 50 to 95% by weight of an organic solvent;(C) from 0.5 to 10% by weight of a dispersing agent of formula:(R.sub.H -L).sub.y -(R.sub.F -L).sub.x R.sub.H (I)whereinx is an integer from 1 to 3;y is 0 or 1, with the proviso that x=1 when y=1;R.sub.H is a x-functional radical having an alkylic or polyoxyalkylenic structure;R.sub.F is (per)fluoropolyoxyalkylenic radical;L is a divalent organic group.Such dispersions are utilized for the surface treatment of metals, glass fibers, and the like, and in particular as mould release agents.Type: GrantFiled: June 19, 1998Date of Patent: June 29, 1999Assignee: Ausimont S.p.A.Inventors: Laura Montagna, Ezio Strepparola
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Patent number: 5910614Abstract: Separation process of bifunctional macromolecules having hydroxylic termination from non functional and/or monofunctional macromolecules having hydroxylic termination contained in admixture in perfluoropolyoxyalkylenes (I) comprising the following phases:addition of the macromer (I) to a suspension of stationary phase in polar solvent, said stationary phase being formed by a compound containing sites and/or active groups, capable of establishing bonds or interactions of polar type, or hydrogen bonds, with the hydroxylic terminals of the perfluoropolyoxyalkylenes contained in the mixture of formula (I), the macromer/stationary phase ratio ranging from 2/3 to 1/1 w/w; solvent/(stationary phase+macromer) ratio ranging from 0.8/1 to 1.Type: GrantFiled: July 30, 1997Date of Patent: June 8, 1999Assignee: Ausimont S.p.A.Inventors: Stefano Turri, Claudio Tonelli, Carlo Pogliani
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Patent number: 5902908Abstract: The present inventions provide methods to produce fluorinated vinyl ether by reacting fluorinated carboxylic acid halogenide with a metal compound below the decomposition temperature for the corresponding metal salt in the absence of solvent and then raising the temperature of the produced corresponding metal salt above the decompostion temperature. With these production methods, fluorinated vinyl ether of a high purity can be obtained on an efficient basis.Type: GrantFiled: November 12, 1997Date of Patent: May 11, 1999Assignee: Daikin Industries Ltd.Inventors: Shigeru Morita, Yasuji Iwasaki
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Patent number: 5814698Abstract: Polytetrafluoroethylene (PTFE) dispersions in an organic solvent, comprising:(A) from 2 to 40% by weight of PTFE in powder form;(B) from 50 to 95% by weight of an organic solvent;(C) from 0.5 to 10% by weight of a dispersing agent of formula:(R.sub.H --L).sub.y --(R.sub.F --L).sub.x R.sub.H (I)wherein:x is an integer from 1 to 3;y is 0 or 1, with the proviso that x=1 when y=1;R.sub.H is a x-functional radical having an alkylic or polyoxyalkylenic structure;R.sub.F is (per)fluoropolyoxyalkylenic radical;L is a divalent organic group.Such dispersions are utilized for the surface treatment of metals, glass fibers, and the like, and in particular as mold release agents.Type: GrantFiled: March 22, 1996Date of Patent: September 29, 1998Assignee: Ausimont S.p.A.Inventors: Laura Montagna, Ezio Strepparola
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Patent number: 5807977Abstract: This application is directed to novel fluorinated polymers and prepolymers derived from mono-substituted oxetane monomers having fluorinated alkoxymethylene side-chains and the method of making these compositions. The mono-substituted fluorinated oxetane monomers having fluorinated alkoxymethylene side-chains are prepared in high yield by the reaction of a fluorinated alkoxides with either 3-halomethyl-3-methyloxetane premonomers or aryl sulfonate derivative of 3-hydroxymethyl-3-methyloxetane premonomers. Preparation of a mono-substituted 3-bromomethyl-3-methyloxetane premonomer via a simple, high yield process amenable to commercial scaleup is also disclosed. The fluorinated oxetane monomers of this invention can be readily homo/co-polymerized in the presence of a Lewis acid and polyhydroxy compounds to obtain hydroxy-terminated polyether prepolymers having fluorinated alkoxymethylene side chains.Type: GrantFiled: January 12, 1995Date of Patent: September 15, 1998Assignee: Aerojet General CorporationInventors: Aslam A. Malik, Thomas G. Archibald
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Patent number: 5789534Abstract: The purification process comprises removing carboxylic acids and/or carboxylic acid salts contained as impurities in a fluorinated polyether having at at least one end thereof a terminal vinyl group linked thereto through an amide group-containing linkage by heating, in the presence of an amine compound such as triethylamine and dimethylaminotrimethylsilane, the fluorinated polyether containing said impurities or a reaction mixture obtained after the completion of reaction in a process of producing said fluorinated polyether. According to the purification process, the impurities can be easily removed from said fluorinated polyether. When the thus purified fluorinated polyether is used as a starting material for an addition type curable composition together with a SiH group-containing organosilicon compound, a liquid rubber material excellent in curability and storage stability can be obtained.Type: GrantFiled: August 8, 1996Date of Patent: August 4, 1998Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Noriyuki Koike, Shinichi Sato, Takashi Matsuda
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Patent number: 5777174Abstract: Process for preparing perfluoropolyethers with bromo- or iodo- containing end groups, respectively, by subjecting a peroxidic perfluoropolyether to thermal treatment, in the absence of UV radiation, at temperatures from 120.degree. C. to 280.degree. C. in the presence of bromo- or iodo-containing compounds having, respectively, the following general formulas:T T' T" C Brwherein T, T', T" equal to or different from each other are selected from Br, F, H or R'.sub.f, wherein R'.sub.f is a perfluoroalkylic chain from 1 to 8 carbon atoms;R R' R" C Iwherein R, R', R", equal to or different from each other can be I (iodine), H, F, or R'.sub.f, wherein R'.sub.f has the meaning indicated above.Type: GrantFiled: April 21, 1997Date of Patent: July 7, 1998Assignee: Ausimont S.p.A.Inventors: Giuseppe Marchionni, Pier Antonio Guarda
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Patent number: 5753776Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: June 6, 1995Date of Patent: May 19, 1998Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5719194Abstract: Use of perfluoropolyethers with non reactive terminals or compositions thereof for the prevention and/or the treatment of topical vital infections, in particular of Herpes Simplex I and II and of Herpes Zoster.Type: GrantFiled: June 7, 1996Date of Patent: February 17, 1998Assignee: Ausimont S.p.A.Inventors: Morris A. Mann, Giovanni Pantini
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Patent number: 5703194Abstract: This application is directed to novel fluorinated polymers and prepolymers derived from mono-substituted oxetane monomers having fluorinated alkoxymethylene side-chains and the method of making these compositions. The mono-substituted fluorinated oxetane monomers having fluorinated alkoxymethylene side-chains are prepared in high yield by the reaction of a fluorinated alkoxides with either 3-halomethyl-3-methyloxetane premonomers or aryl sulfonate derivative of 3-hydroxymethyl-3-methyloxetane premonomers. Preparation of a mono-substituted 3-bromomethyl-3-methyloxetane premonomer via a simple, high yield process amenable to commercial scaleup is also disclosed. The fluorinated oxetane monomers of this invention can be readily homo/co-polymerized in the presence of a Lewis acid and polyhydroxy compounds to obtain hydroxy-terminated polyether prepolymers having fluorinated alkoxymethylene side chains.Type: GrantFiled: June 7, 1995Date of Patent: December 30, 1997Assignee: Aerojet-General CorporationInventors: Aslam A. Malik, Thomas G. Archibald
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Patent number: 5672767Abstract: A process for the preparation of a perfluoropolyether having a general formula: ##STR1## as defined hereinbefore, which process includes the direct fluorination with elemental fluorine of a polyether having a general formula: ##STR2## as defined hereinbefore, wherein the fluorination is carried out in the presence of a solvent which is an ether having at least one substituent R.sub.F, wherein R.sub.F is a fluorinated hydrocarbon group. The said solvent ether is preferably a fluorinated volatile ether. The said solvent ether preferably has at least two groups R.sub.F which may be the same or different groups. Each group R.sub.F preferably has from two to four carbon atoms and at least two fluorine atoms. The said solvent ether may be an alicyclic ether having from 3 to 5 carbon atoms in its alicyclic ring.Type: GrantFiled: July 5, 1996Date of Patent: September 30, 1997Assignee: BNFL Fluorochemicals Ltd.Inventors: Richard Dickinson Chambers, Andrew Keith Joel
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Patent number: 5668250Abstract: This application is directed to novel fluorinated polymers and prepolymers derived from mono-substituted oxetane monomers having fluorinated alkoxymethylene side-chains and the method of making these compositions. The mono-substituted fluorinated oxetane monomers having fluorinated alkoxymethylene side-chains are prepared in high yield by the reaction of a fluorinated alkoxides with either 3-halomethyl-3-methyloxetane premonomers or aryl sulfonate derivative of 3-hydroxymethyl-3-methyloxetane premonomers. Preparation of a mono-substituted 3-bromomethyl-3-methyloxetane premonomer via a simple, high yield process amenable to commercial scaleup is also disclosed. The fluorinated oxetane monomers of this invention can be readily homo/co-polymerized in the presence of a Lewis acid and polyhydroxy compounds to obtain hydroxy-terminated polyether prepolymers having fluorinated alkoxymethylene side chains.Type: GrantFiled: June 7, 1995Date of Patent: September 16, 1997Assignee: Aerojet-General CorporationInventor: Aslam A. Malik
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Patent number: 5668251Abstract: This application is directed to novel fluorinated polymers and prepolymers derived from mono-substituted oxetane monomers having fluorinated alkoxymethylene side-chains and the method of making these compositions. The mono-substituted fluorinated oxetane monomers having fluorinated alkoxymethylene side-chains are prepared in high yield by the reaction of a fluorinated alkoxides with either 3-halomethyl-3-methyloxetane premonomers or aryl sulfonate derivative of 3-hydroxymethyl-3-methyloxetane premonomers. Preparation of a mono-substituted 3-bromomethyl-3-methyloxetane premonomer via a simple, high yield process amenable to commercial scaleup is also disclosed. The fluorinated oxetane monomers of this invention can be readily homo/co-polymerized in the presence of a Lewis acid and polyhydroxy compounds to obtain hydroxy-terminated polyether prepolymers having fluorinated alkoxymethylene side chains.Type: GrantFiled: October 5, 1995Date of Patent: September 16, 1997Assignee: Aerojet-General CorporationInventors: Aslam A. Malik, Roland P. Carlson
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Patent number: 5650483Abstract: This application is directed to novel fluorinated polymers and prepolymers derived from mono-substituted oxetane monomers having fluorinated alkoxymethylene side-chains and the method of making these compositions. The mono-substituted fluorinated oxetane monomers having fluorinated alkoxymethylene side-chains are prepared in high yield by the reaction of a fluorinated alkoxides with either 3-halomethyl-3-methyloxetane premonomers or aryl sulfonate derivative of 3-hydroxymethyl-3-methyloxetane premonomers. Preparation of a mono-substituted 3-bromomethyl-3 -methyloxetane premonomer via a simple, high yield process amenable to commercial scaleup is also disclosed. The fluorinated oxetane monomers of this invention can be readily homo/co-polymerized in the presence of a Lewis acid and polyhydroxy compounds to obtain hydroxy-terminated polyether prepolymers having fluorinated alkoxymethylene side chains.Type: GrantFiled: October 5, 1995Date of Patent: July 22, 1997Assignee: Aerojet-General CorporationInventors: Aslam A. Malik, Gerald E. Manser, Thomas G. Archibald
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Patent number: 5639921Abstract: A process for producing difluoromethyl ethers and esters by reacting an ether or an acid with a cadmium, zinc or bismuth compound containing the CF.sub.3 group and selected from the group consisting of Cd(CF.sub.3).sub.2, Zn(CF.sub.3).sub.2, Bi(CF.sub.3).sub.3, CdHal(CF.sub.3), ZnHal(CF.sub.3), BiHal(CF.sub.3).sub.2 and BiHal.sub.2 (CF.sub.3) in the presence of a Lewis acid.Type: GrantFiled: June 15, 1995Date of Patent: June 17, 1997Assignee: Solvay Fluor und Derivate GmbHInventors: Dieter Naumann, Wieland Tyrra, Regina Moeckel
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Patent number: 5637671Abstract: 1) Disclosed herein are new fluorine-containing compounds having polyacetalic structure, of general formula:[Rf.sub.m --CH.sub.2 O(CH.sub.2 O).sub.c --CH.sub.2 --.brket close-st..sub.n (I)where:Rf=a perfluorooxyalkylene chain having Mn from 500 to 5,000;m=4-25;c=1-10;n=2-100.2) A process for preparing them which comprises carrying out the polycondensation of diols having formula:HORfOH (II)with formaldehyde, in mass or in the presence of solvents, in an acid medium. The compounds of formula (I) can be oligomeric compounds (polymerization degree x.sub.n from 2 to about 20) or polymeric compounds (x.sub.n from about 20 to about 100). They exhibit a high stability to heat and to chemical agents, and Tg values slightly different from the ones of the diols utilized for preparing them.Type: GrantFiled: October 12, 1995Date of Patent: June 10, 1997Assignee: Ausimont S.p.A.Inventors: Ferdinando Danusso, Ezio Strepparola, Marinella Levi, Claudio Tonelli, Stefano Turri
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Patent number: 5608116Abstract: The present invention relates to the preparation of fluoroalkylalkoxylates in which one reacts at least one fluorinated alcohol with at least one alkylene epoxide in the presence of a novel catalyst system comprising an iodine source and an alkali metal borohydride.Type: GrantFiled: March 16, 1995Date of Patent: March 4, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventors: Robert A. Halling, Hsu-Nan Huang
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Patent number: 5571870Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: May 10, 1994Date of Patent: November 5, 1996Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5567857Abstract: Mixture of the compounds: F(CF.sub.2).sub.m --(CH.sub.2).sub.n --(OCH.sub.2 CH.sub.2)p--OH wherein m=2 and about 20, but in at least 5 weight % of molecules m is 8 or higher or mixtures of the same, but in no more than 5 weight % of the molecules is m equal to 14 or higher or mixtures of the same; n=1 to 3; & p=1 to 40, but the mixture has an average p=8 to 17.Type: GrantFiled: June 21, 1994Date of Patent: October 22, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventors: Hsu-Nan Huang, Robert A. Halling
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Patent number: 5562808Abstract: A method and apparatus are disclosed for decontaminating a liquid surfactant of a dioxane having a vapor pressure which is higher than the surfactant. A contaminated liquid surfactant is directed through an inclined conduit. A gas is directed into the inclined conduit, whereby the gas contacts the surfactant and transports the dioxane contaminant, which has volatilized in the inclined conduit, out of the inclined conduit, thereby decontaminating the surfactant. The liquid surfactant is discharged from the inclined conduit.Type: GrantFiled: September 21, 1993Date of Patent: October 8, 1996Assignee: Pharm-Eco Laboratories, Inc.Inventors: Yesh P. Sachdeva, Richard L. Gabriel
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Patent number: 5523496Abstract: Perfluoropolyethers and perhalogenated chlorofluoroether polymers are disclosed that can be prepared by fluorinating polymers made by the polymerization of acetals, ketals, polyacetals, polyketals and orthoesters with elemental fluorine.Type: GrantFiled: April 5, 1994Date of Patent: June 4, 1996Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5506309Abstract: This invention pertains to perfluoropolyethers and perhalogenated chlorofluoropolyethers that can be prepared by fluorinating addition polymers made by polymerizing epoxides.Type: GrantFiled: June 6, 1995Date of Patent: April 9, 1996Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhulke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5498359Abstract: A lubricant compound which comprises carbon, hydrogen, fluorine and etheric oxygen atoms and which contains perfluoropolyether chain of the formula (A), a perfluoroalkyl chain of the formula (B) and a polyether chain of the formula (C) in combinations of (A) and (C), (B) and (C), or (A) and (C) and of (B) and (C), in a molecule wherein:A is --(C.sub.n F.sub.2n O).sub.m --,wherein n is an integer of 1 to 10 and m is an integer of at least 1;B is --C.sub.n F.sub.2n --,wherein n is an integer of 1 to 15, andC is --(C.sub.n H.sub.2n O).sub.m --,wherein n is an integer of 1 to 6 and m is an integer of at least 1.Type: GrantFiled: October 24, 1994Date of Patent: March 12, 1996Assignee: Hitachi Maxell, Ltd.Inventors: Sayaka Shinomoto, Kenji Kohno, Yuko Uetani, Noboru Isoe, Kazushi Miyata
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Patent number: 5488181Abstract: Process for preparing peroxidic perfluoropolyethers by oxidation of tetrafluoroethylene with oxygen, in liquid phase comprising a solvent and in the presence of a chemical initiator, at a pressure between 2 and 15 absolute atm and operating with a molar ratio of the tetrafluoroethylene to the chemical initiator higher than 35. The process allows to increase the molecular weight of the perfluoropolyethers at the same content of peroxidic oxygen.Type: GrantFiled: November 16, 1994Date of Patent: January 30, 1996Assignee: Ausimont S.p.A.Inventors: Giuseppe Marchionni, Pier A. Guarda, Maurizio Paganin
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Patent number: 5463019Abstract: 3-Azidomethyl-3-nitratomethyloxetane, a novel oxetane compound, is used as a monomer for the formation of homopolymers and copolymers with other known energetic oxetane monomers. The polyethers of the present invention can be subsequently cured to form elastomers suitable for use as energetic binders in propellant formulations or the like.Type: GrantFiled: January 23, 1995Date of Patent: October 31, 1995Assignee: Aerojet-General CorporationInventors: Gerald E. Manser, Aslam A. Malik, Thomas G. Archibald
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Patent number: 5461117Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: June 13, 1994Date of Patent: October 24, 1995Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5453549Abstract: An extremely reactive and highly copolymerizable hexafluoropropylene oxide oligoether derivative, to give bi- or ter-polymers with fluoroolefins and perfluoroalkyl vinyl ethers, which is represented by general formula: ##STR1## wherein X is a fluorine atom or trifluoromethyl group; and n is an integer of 2-5.Type: GrantFiled: May 6, 1993Date of Patent: September 26, 1995Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Noriyuki Koike, Kouichi Yamaguchi, Hiromasa Yamaguchi, Kouji Takano
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Patent number: 5449825Abstract: Process for preparing haloperfluoro and perfluoro ethers wherein a metal halide is reacted with a 3-haloperfluoropropene oxide to obtain a 2,3-dihaloperfluorocarbonyl fluoride; a metal halide, 2,3-dihaloperfluorocarbonyl fluoride and 3-haloperfluoropropene oxide are reacted to obtain a 2-(2',3'-dihaloperfluoropropoxy)-3-haloperfluoropropionyl fluoride; 2-(2',3'-dihaloperfluoropropoxy)-3-haloperfluoropropionyl fluoride is decarboxylated and dehalogenated to obtain perfluorovinylallylether. Alternatively, 2-(2',3'-dihaloperfluoropropoxy)-3-haloperfluoropropionyl fluoride is reacted with metal halide and 3-haloperfluoropropene oxide to obtain a 2-[2'-(2",3"-dihaloperfluoropropoxy)-3'-haloperfluoropropoxy]-3-haloperflu oropropionyl fluoride, or a higher polyether, and 2-[2'-(2",3"-dihaloperfluoropropoxy)-3'-haloperfluoropropoxy]-3-haloperflu oropropionyl fluoride or the polyether is decarboxylated and dehalogenated to obtain a 3,6-dioxa-5-halodifluoromethylperfluoronona-1,8-diene or the corresponding polyether.Type: GrantFiled: January 18, 1994Date of Patent: September 12, 1995Assignee: The Dow Chemical CompanyInventors: Nobuyuki Ishibe, Tien K. Tran, Charles W. Martin
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Patent number: 5446206Abstract: This invention relates to perfluoropolyethers having neutral end groups by a process based on the photooxidation of C.sub.3 F.sub.6 and/or C.sub.2 F.sub.4, thereby obtaining controlled molecular weight products having perfluoroalkyl or perfluorochloroalkyl neutral end groups, with high yields of useful products.Type: GrantFiled: July 25, 1994Date of Patent: August 29, 1995Assignee: Ausimont S.r.l.Inventors: Giuseppe Marchionni, Anna Staccione
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Patent number: 5420359Abstract: Normally liquid chlorofluoroether compositions consisting or consisting essentially of one or a selected mixture of perhalogenated chlorofluoroether compounds are provided by direct fluorination of the corresponding chloroether or chlorofluoroether precursors. The compositions are useful, for example, as heat transfer agents, blood substitutes, and solvents.Type: GrantFiled: October 7, 1993Date of Patent: May 30, 1995Assignees: Minnesota Mining and Manufacturing Company, HemaGen/PFCInventors: George G. I. Moore, Richard M. Flynn, Robert J. Kaufman, Thomas J. Richard
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Patent number: 5354910Abstract: Repeat units having pendant functional groups increase the solubility of polymers containing repeat units of perfluoro-2,2-dimethyl-1,3-dioxole.Type: GrantFiled: February 1, 1994Date of Patent: October 11, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ming-Hong Hung, Paul R. Resnick
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Patent number: 5349093Abstract: A fluorovinyl ether of the formula:R.sub.f --(OCF.sub.2 CF.sub.2 CF.sub.2).sub.n --OCF.dbd.CF.sub.2(I)wherein R.sub.f is a C.sub.1- -C.sub.5 perfluoroalkyl group, n is an integer of 1 to 4 provided that when n is 1 (one), R.sub.f is other than a trifluoromethyl group, a copolymer of which with an ethylenically unsaturated compound has a low glass transition temperature and improved low temperature properties.Type: GrantFiled: March 11, 1993Date of Patent: September 20, 1994Assignee: Daikin Industries, Ltd.Inventors: Masahiko Oka, Mitsuru Kishine, Hideya Saito, Masuo Kokumai
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Patent number: 5332790Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: March 8, 1993Date of Patent: July 26, 1994Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5322904Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: March 8, 1993Date of Patent: June 21, 1994Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5322903Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: January 17, 1992Date of Patent: June 21, 1994Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow