Fluorine Patents (Class 568/683)
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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: 5476974Abstract: Normally liquid, omega-hydrofluoroalkyl ether compounds (and selected mixtures thereof) have a saturated perfluoroaliphatic chain of carbon atoms interrupted by one or more ether oxygen atoms. The compounds can be prepared, e.g., by decarboxylation of the corresponding fluoroalkyl ether carboxylic acids and are useful, e.g., in cleaning and drying applications.Type: GrantFiled: May 20, 1994Date of Patent: December 19, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventors: George G. I. Moore, Miguel A. Guerra
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Patent number: 5463139Abstract: A composition comprising bis(fluoromethyl)ether and less than an equimolar amount of water, a process for the production of the composition comprising contacting formaldehyde with hydrogen fluoride and separating at least some of the by-product water from bis(fluoromethyl)ether, and use of the composition for the production of difluoromethane.Type: GrantFiled: June 29, 1994Date of Patent: October 31, 1995Assignee: Imperial Chemical Industries PLCInventors: Jane L. Butcher, Thomas A. Ryan, Leslie Burgess
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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: 5410095Abstract: A process for the manufacture of pentafluorodimethyl ether is disclosed which involves contacting at least one starting compound selected from the group consisting of compounds having a formula (CF.sub.3 OCF.sub.2 CO.sub.2)A and compounds having he formula (CF.sub.3 OCF.sub.2 CO.sub.2).sub.2 A' wherein A is selected from the group consisting of hydrogen, ammonium, alkali metals (e.g., sodium or potassium) and R (wherein R is a C.sub.1 to C.sub.4 alkyl group) and A' is an selected from the group consisting of alkaline-earth metals (e.g., magnesium or calcium), with at least one hydroxylic compound selected from the group consisting of water, mono-alcohols of the formula R'OH (wherein R' is a C.sub.1 to C.sub.12 straight or branched chain alkyl group) and alkanediols of the formula R" (OH).sub.2 (wherein R" is a C.sub.2 to C.sub.8 alkylene group) at temperature of about 120.degree. C. to 170.degree. C.Type: GrantFiled: July 29, 1994Date of Patent: April 25, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Paul R. Resnick, Allen C. Sievert
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Patent number: 5401886Abstract: Disclosed herein is a partially fluorinated polymer containing cyclic units. The polymer is particularly useful in for coatings and encapsulants. Also disclosed herein is the novel monomer from which the polymer is made, and a novel intermediate for that monomer.Type: GrantFiled: May 19, 1994Date of Patent: March 28, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Zhen-Yu Yang
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Patent number: 5386064Abstract: A process for the production of bis(fluoromethyl)ether which comprises contacting formaldehyde with hydrogen fluoride in the presence of an essentially water-immiscible solvent for the ether. The bis(fluoromethyl)ether may be converted to difluoromethane, optionally after separation from the solvent, preferably by heating the bis(fluoromethyl)ether to elevated temperature in the presence of a metal, metal oxide, metal fluoride or metal oxyfluoride catalyst.Type: GrantFiled: April 19, 1993Date of Patent: January 31, 1995Assignee: Imperial Chemical Industries PLCInventors: Duncan C. Woodcock, Brian T. Grady
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Patent number: 5382704Abstract: A process is disclosed for producing a fluorinated ether of the formula R.sub.2 CHOCF.sub.2 A, where A is Cl or F, and each R is H, (CF.sub.2).sub.n Cl, (CF.sub.2).sub.n F or (CF.sub.2).sub.n H (n is an integer from 1 to 10) by reacting a first reactant of the formula R.sub.2 CHOY where Y is H, COF, COCl or COOCHR.sub.2 (R is as defined above), a second reactant selected of the formula CZ.sub.2 Cl.sub.2 or COZ.sub.2 where each Z is independently Cl or F (provided that when A is Cl, the second reactant is CZ.sub.2 Cl.sub.2), and HF; and recovering the fluorinated ether from the reaction products. Also disclosed are bis-ethers of the formula (CF.sub.3 (CF.sub.2).sub.m).sub.2 CHOCF.sub.2 OCH(CF.sub.2).sub.m CF.sub.3).sub.2, where m is an integer of 0 to 3, which can also be produced by the process.Type: GrantFiled: June 30, 1993Date of Patent: January 17, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Carl G. Krespan, V. N. Mallikarjuna Rao
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Patent number: 5371300Abstract: The present invention relates to novel chloro-(2-halogeno-1-fluoromethyl-ethoxy)-methanes and to their preparation. The novel compounds can be used as intermediates for the preparation of biologically active substituted benzimidazoles.Type: GrantFiled: October 29, 1993Date of Patent: December 6, 1994Assignee: Bayer AktiengesellschaftInventors: Stefan Bohm, Albrecht Marhold
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Patent number: 5344580Abstract: Oligomers of compounds of the formulaX--(CF.sub.2).sub.a --O.sub.b --(CH.sub.2).sub.c --CH=CH.sub.2( 1)and co-oligomers of compounds of the formula (1) together with compounds of the formulaX--(CX.sub.2).sub.d --O.sub.b --(CX.sub.2).sub.c --CX=CX.sub.2( 2)in which X is hydrogen or fluorine, a is a number from 2 to 16, b and c are, independently of one another, 0 or 1, and d is a number from 0 to 6, with a mean degree of oligomerization of 2 to 4, are obtained by heating a solution of the monomers in a hydrocarbon together with a free radical-forming catalyst to 135.degree. to 180.degree. C. The oligomers are lubricating agents and lubricants.Type: GrantFiled: December 1, 1992Date of Patent: September 6, 1994Assignee: Hoechst AktiengesellschaftInventor: Konrad von Werner
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Patent number: 5344998Abstract: A process for the production of bis(fluoromethyl)ether by contacting formaldehyde with hydrogen fluoride in a reaction/distillation vessel. The reaction/distillation vessel is preferably a reaction/distillation column through which formaldehyde and hydrogen fluoride preferably flow in counter current.The bis(fluoromethyl)ether may be converted to difluoromethane, preferably by heating the bis(fluoromethyl)ether to elevated temperature in the presence of a metal, metal oxide, metal fluoride or metal oxyfluoride catalyst.Type: GrantFiled: November 4, 1993Date of Patent: September 6, 1994Assignee: Imperial Chemical Industries PLCInventors: John S. Martin, Thomas A. Ryan, Rachel A. Spooncer
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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: 5324864Abstract: A novel process for synthesizing difluoromethyl methyl ether for use as regrigerants and blowing agents, etc. is hereby disclosed. This process involves (1) feeding chlorodifluoromethane at a rate from about 0.5 to 5 grams of feed gas per gram of solution per minute through a sodium methoxide in methanol or basic ion exchange slurry in methanol; (2) removing the gaseous product and the unreacted chlorodifluoromethane continuously; and (3) separating difluoromethyl ether from the unreacted chlorodifluoromethane.Type: GrantFiled: December 18, 1992Date of Patent: June 28, 1994Assignee: Hampshire Chemical Corp.Inventors: Felix B. Popper, Gerald J. O'Neill, Robert J. Bulka
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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
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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: 5283372Abstract: A process for the preparation of highly purified optical isomers of desflurane, i.e. 2-(difluoromethoxy)-1,1,1,2-tetrafluoroethane, is described wherein the highly purified opposite optical isomer of iso-flurane is reacted with bromine trifluoride in the cold, preferably in the presence of a solvent. A preferred solvent is bromine. The highly purified positive isomer of desflurane is advantageous over the negative isomer or the racemate.Type: GrantFiled: April 15, 1993Date of Patent: February 1, 1994Assignee: Anaquest, Inc.Inventors: Leonid A. Rozov, Chialang Huang, Donald F. Halpern, Gerald G. Vernice
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Patent number: 5278342Abstract: The synthesis of fluorinated dimethyl ethers of the formula CF.sub.2 HOCCl.sub.x F.sub.y H.sub.3-(x+y) wherein x is 0, 1 or 2; y is 1, 2 or 3; and wherein (x+y) is 1, 2 or 3. The process involves chlorination of methyl difluoromethyl ether in the presence of oxygen to form a chlorinated reaction product of the formula CF.sub.2 HOCH.sub.3-z Cl.sub.z wherein z is 1 or 2, and wherein the formation of CF.sub.2 HOCCl.sub.3 is inhibited. The resulting compound(s) is then fluorinated with HF before or after separation, to give a fluorinated reaction product including the aforementioned fluorinated dimethyl ethers.Type: GrantFiled: March 15, 1993Date of Patent: January 11, 1994Assignee: Hampshire Chemical Corp.Inventors: Gerald J. O'Neill, Robert J. Bulka
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Patent number: 5260492Abstract: Disclosed herein are novel monomers of the formula CF.sub.2 .dbd.CF(CF.sub.2).sub.n CH.sub.2 OCF.dbd.CF.sub.2, wherein n is 1, 2 or 3, and novel intermediates of the formula CF.sub.2 ClCFCl(CF.sub.2).sub.n CH.sub.2 OCF.dbd.CF.sub.2 wherein n is 1, 2 or 3. Also disclosed is a fluoropolymer containing cyclic units when the monomer wherein n is 1 is free radically polymerized. The polymer is particularly useful in for coatings and encapsulants.Type: GrantFiled: December 21, 1992Date of Patent: November 9, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: Andrew E. Feiring, Bruce E. Smart, Zhen-Yu Yang
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Diluent for perfluorocarbons employed for retinal unfolding (unfolding PFCL) and method of treatment
Patent number: 5244924Abstract: A diluent for perfluorocarbons used for retinal unfolding (unfolding PFCL), consisting of a perfluorocarbon (diluent PFCL), which has a low viscosity and is volatile at room temperature, with a boiling point between body temperature (about 38.degree. C.) and 100.degree. C., for removing residual quantities of unfolding PFCL from the eye after performance of a retinal unfolding treatment. A method of treatment consisting of introducing into an eye the above diluent for the above purpose.Type: GrantFiled: January 24, 1992Date of Patent: September 14, 1993Assignee: Adatomed Pharmazeutische und Medizintechnische Gesellschaft mbHInventor: Hasso Meinert -
Patent number: 5233094Abstract: The invention relates to a process for the preparation of perfluorinated ethers of the formula (I)R--CF.sub.2 --CF.sub.3 (I)in which R is the radical CF.sub.3 (CF.sub.2).sub.2 --O--[CF(CF.sub.3)CF.sub.2 --O].sub.n --, in which n is an integer from 0 to 60, from compounds of the formula (II)R--[CF(CF.sub.3)CF.sub.2 --O--]CHF--CF.sub.3 (II)by heating these at 150.degree.-350.degree. C. in the presence of at least one of the compounds AlCl.sub.3, Albr.sub.3 or AlF.sub.3.Type: GrantFiled: November 12, 1992Date of Patent: August 3, 1993Assignee: Hoechst AktiengesellschaftInventor: Matthias Meyer
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Patent number: 5220076Abstract: The invention relates to new peroxide perfluoropolyethers having formula: ##STR1## wherein: A and B are end groups,X represents a (R'O).sub.m R" group where R' is selected from the class consisting of --CF.sub.2 --, --CF.sub.2 --CF.sub.2 -- and ##STR2## and R" is a perfluoroalkyl group; the value of "m" ranging from 0 to 6. The invention relates also to processes for preparing said perfluoropolyethers and other classes of non peroxide perfluoropolyethers derived therefrom.Type: GrantFiled: May 29, 1992Date of Patent: June 15, 1993Assignee: Ausimont S.r.l.Inventors: Antonio Marraccini, Antonio Pasquale, Anna M. Staccione, Giuseppe Marchionni
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Patent number: 5214214Abstract: There is provided a novel perfluorochemical represented by the formula, ##STR1## wherein R.sub.F is a perfluoroalkyl group, a perfluoro alkoxyalkyl group or a perfluoroalkyloxy group, X and X' are same as or different from each other and are a fluorine atom or a perfluoroalkyl group, and Y is a perfluoroalkyloxy group or a perfluoro dialkylamino group, the total number of the carbon atoms contained being an integer of 8 to 11 inclusive. The perfluorochemical is prepared by perfluorinating the corresponding partially fluorinated compound which may have unsaturated hydrocarbon moiety, only with molecular fluorine in a stoichiometric excess amount in an inert solvent.The perfluorochemical is used for preparing a stable emulsion as blood substitutes or perfusion media.Type: GrantFiled: March 30, 1992Date of Patent: May 25, 1993Assignee: The Green Cross CorporationInventors: Kirby V. Scherer, Jr., Kouichi Yamanouchi, Kazumasa Yokoyama, Kimie Naito
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Patent number: 5205914Abstract: An improved preparation of desflurane, 1,2,2,2-tetrafluoroethyl difluoromethyl ether utilizing hexafluoropropene epoxide as a starting material. Hexafluoropropene epoxide is advantageous in that it is relatively inexpensive and is environmentally acceptable.Type: GrantFiled: August 14, 1992Date of Patent: April 27, 1993Assignee: Anaquest, Inc.Inventors: Leonid A. Rozov, Chialang Huang, Gerald G. Vernice
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Patent number: 5196600Abstract: A novel process is disclosed for the synthesis of fluorinated dimethyl ethers of the formula CF.sub.2 HOCCl.sub.x F.sub.y H.sub.3-(x+y) wherein x is 0, 1 or 2; y is 1, 2 or 3; and wherein the total x+y is 1, 2 or 3. The process involves chlorination of methyl difluoromethyl ether to form a chlorinated reaction product, including at least one compound of the formula CF.sub.2 HOCH.sub.3-z Cl.sub.z, wherein z is 1, 2 or 3, which compound is then fluorinated with HF and/or an antimony salt and with or without separation from the chlorinated reaction product, to give a fluorinated reaction product including the aforementioned fluorinated dimethyl ethers.Type: GrantFiled: March 25, 1992Date of Patent: March 23, 1993Assignee: W. R. Grace & Co.-Conn.Inventor: Gerald J. O'Neill
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Patent number: 5189227Abstract: 1,2,4-Trihalobutyl ethers of the formula ##STR1## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 -cycloalkyl that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or cyano, which are useful as intermediates for the preparation of cyclopropanecarbaldehydes.Type: GrantFiled: August 30, 1990Date of Patent: February 23, 1993Assignee: Ciba-Geigy CorporationInventors: Hans-Ruedi Kanel, John G. Dingwall
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Patent number: 5185474Abstract: A novel process is disclosed for the synthesis of fluorinated dimethyl ethers of the formula CF.sub.2 HOCCl.sub.X F.sub.Y H.sub.3-(X+Y) wherein X and Y are each independently 0, 1, 2 or 3 and wherein the total X+Y is 2 or 3. The process involves chlorination of methyl difluoromethyl ether to form a chlorinated reaction product, including at least one compound of the formula CF.sub.2 HOCH.sub.3-z Cl.sub.z, wherein z is 1, 2 or 3, which compound is then fluorinated, with or without separation from the chlorinated reaction product, to give a fluorinated reaction product including the aforementioned fluorinated dimethyl ethers.Type: GrantFiled: April 27, 1992Date of Patent: February 9, 1993Assignee: W. R. Grace & Co.-Conn.Inventor: Gerald J. O'Neill
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Patent number: 5132455Abstract: This invention relates to perfluoroether compounds, and to a general method for creating such compounds. It has been found that such compounds may be created by a three-step method which may be performed using a wide variety of ester starting materials. The first step of the three-step process comprises partial fluorination of a selected polyester compound. This may be performed by contacting the selected polyester with fluorine gas under predetermined conditions until a desired level of partial fluorination is achieved.The second step of this three-step process involves indirect fluorination to convert the partially fluorinated polyester into partially fluorinated polyether compounds. This step may be conducted by contacting the partially fluorinated polyester with SF.sub.4.The third step of the three-step synethetic process comprises direct fluorination of the partially fluorinated polyether compound at conditions which essentially complete the perfluorinated polyether compound.Type: GrantFiled: January 16, 1991Date of Patent: July 21, 1992Assignee: Exfluor Research CorporationInventor: Richard J. Lagow
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Patent number: 5093432Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: September 28, 1989Date of Patent: March 3, 1992Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5087775Abstract: A process for the preparation of partially fluorinated alcohols starting from halogen-containing alkenes, and 2,2,3,3,4,4-hexafluorocyclopentanol as a new partially fluorinated alcohol.Type: GrantFiled: October 24, 1990Date of Patent: February 11, 1992Assignee: Bayer AktiengesellschaftInventors: Karl-Rudolf Gassen, Dietmar Bielefeldt, Michael Negele, Heinz Ziemann
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Patent number: 5087765Abstract: In the process for preparing chlorotrifluoroethylene telomers by reaction of chlorotrifluoroethylene with CF.sub.3 CF or R.sub.x --CF.sub.2 OF (wherein R.sub.x may be also a perfluoroalkyl radical having 1 to 10 carbon atoms), the content of telomers with end groups --F is increased or mixtures of telomers containing species with end groups --Cl are obtained by adding F.sub.2, according to particular modalities, to the reaction medium.Type: GrantFiled: January 11, 1990Date of Patent: February 11, 1992Assignee: Ausimont S.r.L.Inventors: Antonio Marraccini, Antonio Pasquale, Marco Vincenti
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Patent number: 5083082Abstract: Perfluoropolyethers having an average molecular weight higher than 390 and respectively having a kinematic viscosity lower than 8.5 cSt (at 20.degree. C.), and such as to distill by not more than 10% at temperatures lower than 140.degree. C., and by at least 90% at temperatures not higher than 260.degree. C., or, in the case in which the perfluoropolyether does not contain CF (CF.sub.3) CF.sub.2 O units, having a viscosity lowr than 18 cSt (at 20.degree. C.), and such as to distill by not more than 10% at temperatures lower than 140.degree.C., and by at elast 90% at temperatures not higher than 280.degree. C., are used as the only high-temperature and low-temperature working fluid in the Thermal Shock Tests to which the electronic components are submitted, and at the same time are advantageously used in other tests used in the electronic industry, such as the Gross Leak Test and the Burn in Test, allowing the operators in this field to use only single fluid for a whole set of uses.Type: GrantFiled: April 24, 1990Date of Patent: January 21, 1992Assignee: Montedison S.p.A.Inventors: Gianangelo Bargigia, Gerardo Caporiccio, Claudio Tonelli, Luciano Flabbi, Giuseppe Marchionni
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Patent number: 5026924Abstract: A process is provided for the low temperature preparation of CF.sub.3 CHFOCHF.sub.2 which comprises reacting CF.sub.3 CHClOCHF.sub.2 with hydrogen fluoride in the presence of an antimony pentachloride catalyst or mixture of antimony pentachloride and antimony trichloride.Type: GrantFiled: January 4, 1990Date of Patent: June 25, 1991Assignee: Anaquest, Inc.Inventor: Charles F. Cicco
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Patent number: 5017718Abstract: A process for preparing a perfluoroalkyl-substituted compound is disclosed. The process comprises reacting a halopolyfluoroalkane having 1 to 20 carbon atoms with a compound selected from the group consisting of (1) a substituted or unsubstituted ethylene, (2) a substituted or unsubstituted acetylene and (3) a substituted or unsubstituted allylsilane, in the presence of a metal-carbonyl complex of the metal of the Group VIII of the Periodic Table. Alternatively, the reaction between the halopolyfluoroalkane and the substituted or unsubstituted allylsilane is effected under radical generating condition.Type: GrantFiled: January 26, 1984Date of Patent: May 21, 1991Assignee: Sagami Chemical Research CenterInventors: Iwao Ojima, Takamasa Fuchikami
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Patent number: 5015781Abstract: The present invention is directed to a method of preparing a compound 2-(difluoromethoxy)-1,1,1,2-tetrafluoroethane by reacting 2-(difluoromethoxy)-1,1,1-trifluoro-2-chloroethane with bromine trifluoride. This reaction product is useful for inducing and maintaining anesthesia in warm blooded animals.Type: GrantFiled: May 18, 1990Date of Patent: May 14, 1991Assignee: BOC, Inc.Inventors: Mark L. Robin, Donald F. Halpern
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Patent number: 5013472Abstract: New chlorotrifluoroethylene telomers and process for preparing them. Chlorotrifluoroethylene is reacted, at a temperature ranging from -100.degree. to +40.degree. C., with a fluoroxy compound of formula R.sub.x --CF.sub.2 OF, wherein R.sub.x represents among others a perhalogenated alkyl radical containing from 1 to 10 carbon atoms. There are obtained telomer mixtures having, among others, the following formulae: R.sub.x --CF.sub.2 --O--(M).sub.n --F; R.sub.x --CF.sub.2 --O--(M).sub.n --O--CF.sub.2 --R.sub.x ; R.sub.x --(M).sub.n --F; R.sub.x (M).sub.n --R.sub.x ; R.sub.x --CF.sub.2 --O--(M).sub.n --R.sub.x and F--(M).sub.n --F; wherein M is CF.sub.2 --CFCL and "N" ranges from 2 to 20. Most of these telomers are new compounds.Type: GrantFiled: December 23, 1988Date of Patent: May 7, 1991Assignee: Ausimont S.R.L.Inventors: Antonio Marraccini, Gabriele Perego, Giovanni Guastalla
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Patent number: 4996371Abstract: The present invention is directed to a method for replacing a carboxylic acid group with a fluorine group in a halogenated aliphatic carboxylic acid compound having the formula, R-COOH, to prepare a fluorinated product having the formula, R-F, wherein R is a halogenated aliphatic group including straight- and branched-chain aliphatic groups selected from the group consisting of halogenated aliphatic and alkoxy-substituted halogenated aliphatic groups, wherein the method comprises the steps of (a) reacting the halogenated aliphatic carboxylic acid compound with bromine trifluoride, and (b) recovering the fluorinated product.Type: GrantFiled: January 16, 1990Date of Patent: February 26, 1991Assignee: BOC, Inc.Inventors: Donald F. Halpern, Mark L. Robin
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Patent number: 4973716Abstract: A process for fluorinating hydrogenated ethereal compounds by direct reaction with elemental F.sub.2 diluted with an inert gas, wherein the starting compound is in the liquid phase, said fluorination being carried out in the presence of a per fluoropolyetheral compound and of an alkaline metal fluoride.Type: GrantFiled: December 11, 1989Date of Patent: November 27, 1990Assignee: Ausimont S.p.A.Inventors: Pierangelo Calini, Silvana Modena
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Patent number: 4968836Abstract: The invention relates to a process for the preparation of cyclopropanecarbaldehydes of formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl, which comprises (a) reacting a tetrahydrofuran of formula ##STR2## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 -cycloalkyl that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or cyano, with a halogenating agent to form a 1,2,4-trihalobutyl ether of formula ##STR3## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 cycloalkyl that is unsubstituted or substituted by halogen C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.Type: GrantFiled: January 30, 1990Date of Patent: November 6, 1990Assignee: Ciba-Geigy CorporationInventors: Hans-Ruedi Kanel, John G. Dingwall
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Patent number: 4957986Abstract: Partially fluorinated polyesters are disclosed having increased biodegradability and water repellency. The incorporation of an ester group into the backbone of the partially fluorinated compound permits modification of the compound's physical properties.Type: GrantFiled: December 15, 1989Date of Patent: September 18, 1990Assignee: E. I. Du Pont de Nemours and CompanyInventor: Harry N. Cripps
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Patent number: 4955726Abstract: Perfluoropolyethers having an average molecular weight higher than 390 and respectively having a kinematic viscosity lower than 8.5 cSt (at 20.degree. C.), and such as to distill by not more than 10% at temperatures lower than 140.degree. C., and by at least 90% at temperatures not higher than 260.degree. C., or, in the case in which the perfluoropolyether does not contain CF(CF.sub.3)CF.sub.2 O units, having a viscosity lower than 18 cSt (at 20.degree. C.), and such as to distill by not more than 10% at temperatures lower than 140.degree. C., and by at least 90% at temperatures not higher than 280.degree. C., are used as the only high-temperature and low-temperature working fluid in the Thermal Shock Tests to which the electronic components are submitted, and at the same time are advantageously used in other tests used in the electronic industry, such as the Gross Leak Test and the Burn in Test, allowing the operators in this field to use one single fluid for a whole set of uses.Type: GrantFiled: May 16, 1988Date of Patent: September 11, 1990Assignee: Montedison S.p.A.Inventors: Gianangelo Bargigia, Gerardo Caporiccio, Claudio Tonelli, Luciano Flabbi, Giuseppe Marchionni
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Patent number: 4943595Abstract: There is provided a novel perfluorochemical represented by the formula, ##STR1## wherein R.sub.F is a perfluoroalkyl group, a perfluoro alkoxyalkyl group or a perfluoroalkyloxy group, X and X' are same as or different from each other and are a fluorine atom or a perfluoroalkyl group, and Y is a perfluoroalkyloxy group or a perfluoro dialkylamino group, the total number of the carbon atoms contained being an integer of 8 to 11 inclusive. The perfluorochemical is prepared by perfluorinating the corresponding partially fluorinated compound which may have unsaturated hydrocarbon moiety, only with molecular fluorine in a stoichiometric excess amount in an inert solvent.The perfluorochemical is used for preparing a stable emulsion as blood substitutes or perfusion media.Type: GrantFiled: February 22, 1984Date of Patent: July 24, 1990Assignee: The Green Cross CorporationInventors: Kirby V. Scherer, Jr., Kouichi Yamanouchi, Kazumasa Yokoyama, Ryoichi Naito, deceased
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Patent number: 4902835Abstract: New chemical reactions of 1,1,2-trifluoro-1,3-butadiene provide simple access to a series of new fluorinated alkene derivatives. These derivatives provide a simple, general methodology for the stereocontrolled preparation of 2-fluoro-2-alkenoate esters and related monofluoroalkene derivatives which include fluoro analogs of known insecticides, pheromones or pharmaceuticals. A new method for the preparation of 1,1,2-trifluoro-1,3-butadiene is also provided.Type: GrantFiled: January 11, 1988Date of Patent: February 20, 1990Assignee: The University of RochesterInventors: Andrew S. Kende, Noritada Matsuo
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Patent number: 4874901Abstract: Sodium or potassium fluoride has been found to efficiently fluorinate the chloro atom adjacent the ether oxygen in chloro-fluoro organic ethers. The reaction proceeds efficiently without added solvent at an elevated temperature and pressure.Type: GrantFiled: May 6, 1988Date of Patent: October 17, 1989Assignee: BOC, Inc.Inventors: Donald F. Halpern, Mark L. Robin
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Patent number: 4874902Abstract: Fluoromethyl 1,1,1,3,3,3-hexafluoro-2-propyl ether is prepared by reacting bromine trifluoride and methyl 1,1,1,3,3,3-hexachloro-2-propyl ether or chloromethyl 1,1,1,3,3,3-hexachloro-2-propyl ether. The mixed fluorochloro ether intermediates having the formula of ##STR1## (wherein x+y=3, a+b=3, and Z=H Cl, or F) are converted to fluoromethyl 1,1,1,3,3,3-hexafluoro-2-propyl ether by reactions with bromine trifluoride.Type: GrantFiled: May 20, 1988Date of Patent: October 17, 1989Assignee: BOC, Inc.Inventors: Chialang Huang, Gerald G. Vernice
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Patent number: 4859747Abstract: The direct fluorination of ethers in the presence of hydrogen fluoride (HF) scavengers such as sodium fluoride and potassium fluoride is disclosed. Ethers (liquid or solid) are either mixed with the HF scavenger, coated onto the HF scavenger or placed separately with the HF scavenger into a fluorination reactor and fluorinated by exposure to elemental fluorine. The HF scavenger permits use of more severe fluorination conditions than would be possible in the absence of the scavenger, i.e. higher initial fluorine, less gradual increases in fluorine gas concentrations and greater fluorine gas flow rates.Type: GrantFiled: May 24, 1988Date of Patent: August 22, 1989Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Richard J. Lagow
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Patent number: 4855460Abstract: A process for the preparation of perfluoroalkylated ketones and/or perfluoroalkylated alcohols, comprising the step of contacting a perfluoroalkyl iodide or perfluoroalkyl bromide with an acid anhydride, in the presence of a metal chosen from zinc and cadmium.Type: GrantFiled: July 11, 1988Date of Patent: August 8, 1989Assignee: Rhone-Poulenc ChimieInventors: Marc Tordeux, Claude Wakselman, Catherine Francese
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Patent number: 4855511Abstract: Process for preparing CHF.sub.2 OCHFCF.sub.3 through the use of novel intermediate compounds CHCl.sub.2 OCH.sub.2 COCl and CHCl.sub.2 OCHClCOCl.Type: GrantFiled: July 18, 1988Date of Patent: August 8, 1989Assignee: BOC, Inc.Inventors: Donald F. Halpern, Mark L. Robin
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Patent number: 4845268Abstract: A halogen-containing polyether comprising repeating units of the formula:--(CH.sub.2 CF.sub.2 CF.sub.2 O).sub.2 --(CHClCF.sub.2 CF.sub.2 O).sub.b --(CCl.sub.2 CF.sub.2 CF.sub.2 O).sub.c --(CHFCF.sub.2 CF.sub.2 O).sub.d --(CFClCF.sub.2 CF.sub.2 O).sub.e --(CF.sub.2 CF.sub.2 CF.sub.2 O).sub.f --(I)wherein a, b, c, d, e and f are each an integer not less than 0 and satisfy the following equations:2.ltoreq.a+b+c+d+e+f.ltoreq.200and1.ltoreq.a+c+d+f,which may be prepared by ring-opening polymerizing 2,2,3,3-tetrafluorooxetane in the presence of an polymerization initiator to give a polyether comprising repeating units of the formula:--(CH.sub.2 CF.sub.2 CF.sub.2 O).sub.a -- (II)wherein a is the same as defined above, and optionally fluorinating and/or chlorinating the polyether (II).Type: GrantFiled: December 9, 1986Date of Patent: July 4, 1989Assignee: Daikin Industries, Ltd.Inventors: Yohnosuke Ohsaka, Takashi Tohzuka, Shoji Takaki
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Patent number: 4836944Abstract: A halogen-containing polyether which comprises a repeating unit structure of the formula:--(CH.sub.2 CF.sub.2 CF.sub.2 O).sub.a --(CHClCF.sub.2 CF.sub.2 O).sub.b --(CCl.sub.2 CF.sub.2 CF.sub.2 O).sub.c --(CHFCF.sub.2 CF.sub.2 O).sub.d --(CFClCF.sub.2 CF.sub.2 O).sub.e --(CF.sub.2 CF.sub.2 CF.sub.2 O).sub.f --(I)wherein a, b, c, d, e and f are each 0 or a positive integer and satisfy the following equations:2.ltoreq.a+b+c+d+e+f.ltoreq.200 and 1.ltoreq.a+c+d+fand at least one terminal group selected from the group consisting of groups represented by the formulas:--CH.sub.2 OH, --COOR.sup.1, --CONR.sup.1.sub.2, --COOOR.sup.2 Ph and --R.sup.2 Phwherein R.sup.1 is a hydrogen atom, a C.sub.1 -C.sub.5 alkyl group or an aromatic group, R.sup.2 is a divalent organic group and Ph is an aromatic group, which has good lubricating properties.Type: GrantFiled: June 1, 1988Date of Patent: June 6, 1989Assignee: Daikin Industries Ltd.Inventors: Takashi Tohzuka, Sueyoshi Ishikawa, Katsuyoshi Kubo, Yoshitaka Honda, Yukio Ohmure, Norio Kataoka
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Patent number: 4755567Abstract: The direct fluorination of ethers in the presence of hydrogen fluoride (HF) scavengers such as sodium fluoride and potassium fluoride is disclosed. Ethers (liquid or solid) are either mixed with the HF scavenger, coated onto the HF scavenger or placed separately with the HF scavenger into a fluorination reactor and fluorinated by exposure to gradually increasing concentrations of fluorine gas. The HF scavenger permits use of more severe fluorination conditions i.e. higher initial fluorine, less gradual increases in fluorine gas concentrations and greater fluorine gas flow rates.Type: GrantFiled: October 27, 1986Date of Patent: July 5, 1988Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Richard J. Lagow