Additional Diverse Halogen Containing Patents (Class 568/684)
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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: 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: 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: 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: 5268511Abstract: A two step process, each of the steps being novel, for the production of trifluorovinyl ethers by reaction of a siloxane with selected acyl fluorides or carboxylic anhydrides, is disclosed. Also disclosed is a novel silyl ester intermediate.Type: GrantFiled: March 27, 1992Date of Patent: December 7, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: William B. Farnham
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Patent number: 5230778Abstract: A method for the separation of Isoflurane from its admixture with other compounds produced in the chlorination of 2-difluoromethoxy-1,1,1-trifluoroethane including subjecting the mixture to distillation, distilling off the Isoflurane and effecting said distillation as an extractive distillation employing an extractive solvent which retards the vapor pressure of Isoflurane.Type: GrantFiled: May 1, 1992Date of Patent: July 27, 1993Assignees: Gavlin Associates, Halocarbon Product CorporationInventors: Gilbert Gavlin, Boris Goltsin
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Patent number: 5198136Abstract: An iodine-containing compound consisting of at least two repeating units selected from the formulae:--(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 --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 and1.ltoreq.a+c+d+fand an iodine atom at at least one end of a molecule, which can provide a block copolymer which is useful as a grease.Type: GrantFiled: March 5, 1990Date of Patent: March 30, 1993Assignee: Daikin Industries Ltd.Inventors: Masayoshi Tatemoto, Yuji Yutani, Koji Fujiwara
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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: 5157066Abstract: A solid surface modifying composition comprising a film forming material and a fluoroalkyl ether ((Rf).sub.m (CONH--X--NHCO--Y).sub.m (m=1 or 2; Rf: perfluoropolyether chain; X: ##STR1## etc.; ##STR2## etc.) provides surfaces with such improvements as durable water and oil repellency, lubricity and lowered surface energy. The lubricating protective coating is applicable for coatings of recording mediums, photoreceptors and wirings.Type: GrantFiled: July 2, 1991Date of Patent: October 20, 1992Assignee: Hitachi, Ltd.Inventors: Mitsuyoshi Shoji, Takayuki Nakakawaji, Yutaka Ito, Shigeki Komatsuzaki, Akio Mukoh
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Patent number: 5114715Abstract: Disclosed is a method of inducing and maintaining anesthesia while avoiding concomitant liability of adverse effects comprising administering by inhalation to a warm blooded animal in need of anesthesia an amount sufficient to induce and maintain anesthesia but insufficient to cause said adverse effects, of (S)-isoflurane or (S)-desflurane, substantially free of its (R)-stereoisomer. Also disclosed are novel compositions of these compounds for use in the above disclosed method.Type: GrantFiled: November 29, 1990Date of Patent: May 19, 1992Assignee: Sepracor Inc.Inventors: James W. Young, Steven Brandt
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Patent number: 5114714Abstract: Disclosed is a method of inducing and maintaining anesthesia while avoiding concomitant liability of adverse effects comprising administering by inhalation to a warm blooded animal in need of anesthesia an amount sufficient to induce and maintain anesthesia but insufficient to cause said adverse effects, of (R)-isoflurane or (R)-desflurane, substantially free of its (S)-stereoisomer. Also disclosed are novel compositions of these compounds for use in the above disclosed method.Type: GrantFiled: November 29, 1990Date of Patent: May 19, 1992Assignee: Sepracor, Inc.Inventors: James W. Young, Steven Brandt
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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: 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: 5051535Abstract: A process is described for the preparation of the title compounds from the corresponding iodine-containing compounds by reaction with bromide or chloride ions present as salts, in a dipolar aprotic solvent, in the presence of a metal complex compound which contains chromium, nickel, cobalt or rhodium as the central atom and contains, per central atom, 1, 2 or 3 bromine or chlorine atoms and at least one additional phosphorus-containing ligand, at 20.degree. to 140.degree. C. Good yields are obtained in this way without the difficulties associated with the known procedure using elemental halogens at elevated temperatures. The compounds prepared can be used in the medical sector and as liquids resistant to high temperatures.Type: GrantFiled: February 14, 1991Date of Patent: September 24, 1991Assignee: Hoechst AktiengesellschaftInventor: Konrad Von Werner
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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: 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: 5001278Abstract: A fluorovinyl ether of the formula:XCH.sub.2 CF.sub.2 CF.sub.2 --(OCH.sub.2 CF.sub.2 CF.sub.2).sub.m --(OCFYCF.sub.2).sub.n --OCF.dbd.CF.sub.2 (I)wherein X is a hydrogen atom or a halogen atom (e.g. fluorine, chlorine, bromine and iodine); Y is a fluorine atom or a trifluoromethyl group; m is an integer of 0 to 5; and n is 0, 1 or 2, which can modify a polymer of at least one ethylenically unsaturated compound.Type: GrantFiled: March 24, 1988Date of Patent: March 19, 1991Assignee: Daikin Industries, Ltd.Inventors: Masahiko Oka, Yuji Yutani, Masayasu Tomoda, Mitsuru Kishine, Tetsuo Shimizu
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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: 4962236Abstract: An iodine-containing compound consisting of at least two repeating units selected from the formulae:--(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 --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 and1.ltoreq.a+c+d+fand an iodine atom at at least one end of a molecule, which can provide a block copolymer which is useful as a grease.Type: GrantFiled: May 1, 1989Date of Patent: October 9, 1990Assignee: Daikin Industries Ltd.Inventors: Masayoshi Tatemoto, Yuji Yutani, Koji Fujiwara
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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: 4947006Abstract: Preparing fluorinated conjugated olefinic products having, among others, the formulae:R.sub.x O--(CF.dbd.CF).sub.m --F (A)R.sub.x O--(CF.dbd.CF).sub.m --OR.sub.x (B)F--(CF.dbd.CF).sub.m --F (C), andR.sub.y --(CF.dbd.CF).sub.m --F (D)wherein:R.sub.x and R.sub.y represent, among others, a perhalogenated alkyl radical containing from 1 to 10 carbon atoms in the case of R.sub.x and from 1 to 9 carbon atoms in the case of R.sub.y, andm is a numeral in the range of from 2 to 10.These olefinic products are obtained by reacting telomeric products having, among others, the formulae:R.sub.x O--(CFCl--CFCl).sub.m --FR.sub.x O--(CFCl--CFCl).sub.m --OR.sub.xF--(CFCl--CFCl).sub.m --F, andR.sub.y --(CFCl--CFCl).sub.Type: GrantFiled: June 29, 1989Date of Patent: August 7, 1990Assignee: AUSIMONT S.r.l.Inventors: Antonio Marraccini, Antonio Pasquale, Tiziana Fiorani
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Patent number: 4937391Abstract: Preparing perfluoro-(2-bromoethyl-vinyl-ether)CBrF.sub.2 --CF.sub.2 --O--CF.dbd.CF.sub.2by the dechlorination of 2-bromo-1',2'-dichloro-perfluorodiethyl-etherCBrF.sub.2 --CF.sub.2 --O--CClF--CClF.sub.2in the presence of copper and a solvent constituted by an aliphatic amide of the formula ##STR1## wherein R.sub.1 and R.sub.2 are either H or (C.sub.1 -C.sub.2)-alkyl groups andR.sub.3 is a (C.sub.1 -C.sub.2)-alkyl group,at temperatures within the range of from 100.degree. up to 160.degree. C.Type: GrantFiled: June 29, 1989Date of Patent: June 26, 1990Assignee: Ausimont S.r.l.Inventor: Claudio Gervasutti
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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: 4900872Abstract: Improved process for the preparation of fluorohalogenated ethers by reaction of a fluorinated fluorooxycompound with a halogenated olefin, performed in liquid phase, in the presence of an inert solvent, at low temperature, the fluoroxycompound being continuously fed in form of solution in an inert solvent.Type: GrantFiled: May 26, 1989Date of Patent: February 13, 1990Assignee: Ausimont S.p.A.Inventors: Giorgio Guglielmo, Gian P. Gamberetto
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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: 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: 4772756Abstract: A process for the preparation of fluoroalkyl ethers of the formula: ##STR1## wherein: Y is Br or F;X is F, Cl or Br or their mixtures when n is equal to or higher than 2;n is within the range of from 0 to 4;R.sub.f represents a perfluoroalkylene radical containing from 1 to 8 carbon atoms.The process is characterized in that a fluoroalkoxy perfluoroacyl fluoride of the formula: ##STR2## is slowly heated with a salifying agent and a solvent, in the presence of a catalytic amount of N,N-dimethylformamide, with an end temperature within the range of from 60.degree. to 150.degree. C. being reached.Type: GrantFiled: September 14, 1987Date of Patent: September 20, 1988Assignee: Ausimont S.p.A.Inventors: Giorgio Bornengo, Michele Pontevivo, Antonio Marraccini, Silvana Modena
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Patent number: 4754085Abstract: Process for the preparation of hydro(halo)fluoroalkanes by direct fluorination in liquid phase with elemental fluorine at low temperature (under 0.degree. C.) of the corresponding hydro(halo)=alkenes.Type: GrantFiled: October 20, 1986Date of Patent: June 28, 1988Assignee: Ausimont S.p.A.Inventors: Claudio Gervasutti, Lino Conte, Gian Paolo Gambaretto
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Patent number: 4724092Abstract: A fluorine-containing grease composition comprising a halogen-containing polyether 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 an integer not less than 0 and satisfy the following equations:2.ltoreq.a+b+c+d+e+f.ltoreq.200and,1.ltoreq.a+c+d+fand 0.5 to 60% by weight of a fluororesin base on the weight of the whole composition, which has good chemical and heat resistance and is used in a high temperature environment.Type: GrantFiled: November 7, 1985Date of Patent: February 9, 1988Assignee: Daikin Industries Ltd.Inventors: Shoshin Fukui, Shuhei Shimasaki, Takashi Tohzuka
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Patent number: 4577044Abstract: Telomers formed by reacting chlorotrifluoroethylene with fluoroxytrifluoromethane are disclosed. The telomerization reaction is conducted in either liquid chlorotrifluoroethylene without a solvent or in solution. The telomers thus formed can optionally be fluorinated by reaction with a suitable fluorinating agent to improve their stability.Type: GrantFiled: February 11, 1985Date of Patent: March 18, 1986Assignee: Occidental Chemical CorporationInventors: Donald H. Campbell, Michael J. Fifolt, Mohan S. Saran
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Patent number: 4554112Abstract: Fluorovinyl compounds having the formulaTLCF.dbd.CF.sub.2are prepared by reacting compounds having the formula ##STR1## for a time and at a temperature sufficient to form the vinyl compound: whereX=Cl, Br or I;Z=F, Cl, Br, OH, NRR', OA, or SA;R and R' are independently selected from the group consisting of hydrogen, an alkyl having one or more than one carbon atom, and aryl;A=Alkali metal, alkali earth metal, quaternary nitrogen, or R;L=oxygen or sulfur; andT=an alkyl or aryl radical which does not interfere with the reaction.Type: GrantFiled: April 30, 1981Date of Patent: November 19, 1985Assignee: The Dow Chemical CompanyInventors: Bobby R. Ezzell, William P. Carl, William A. Mod
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Patent number: 4515989Abstract: Compounds represented by the general formulas ##STR1## are prepared by reacting halofluoropropylene oxides with fluorinated acid fluorides and ketones.Type: GrantFiled: June 11, 1980Date of Patent: May 7, 1985Assignee: The Dow Chemical CompanyInventors: Bobby R. Ezzell, William P. Carl, William A. Mod
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Patent number: 4504686Abstract: 1,1,2-Trifluoro-2-chloroethyl difluoromethyl ether is prepared in a good yield by reacting 1,1,2-trifluoro-2-chloroethyl dichloromethyl ether with hydrogen fluoride at a gaseous phase.Type: GrantFiled: August 1, 1984Date of Patent: March 12, 1985Assignee: Daikin Kogyo Co., Ltd.Inventor: Shuichi Takamatsu
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Patent number: 4433180Abstract: A process is described for the preparation of 2-alkenyl 1,1,2-trifluoro-2-halogenoethyl ethers by reacting optionally substituted allyl alcohols with fluoroolefins in the presence of an alkali metal hydroxide as catalyst, in which the reaction is carried out by intimately mixing the reactants with an N,N-dialkylcarboxylic acid amide. The said ethers are suitable as intermediate products for the preparation of addition products by the addition of alcohols, primary or secondary amines or R.sub.3 SiH compounds, and are also suitable as comonomers for fluorine-containing copolymers.Type: GrantFiled: May 18, 1982Date of Patent: February 21, 1984Assignee: Hoechst AktiengesellschaftInventor: Konrad von Werner
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Patent number: 4431845Abstract: A method for the preparation of hydroxyl-terminated poly(haloalkylene ethers) is disclosed wherein a catalyst system comprising a fluorinated acid and a polyvalent tin compound is utilized.Type: GrantFiled: March 5, 1982Date of Patent: February 14, 1984Assignee: Minnesota Mining and Manufacturing CompanyInventors: Chung I. Young, Loren L. Barber, Jr.
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Patent number: 4423249Abstract: Alkyl or aryl 1,1-difluoroalkyl ethers, e.g., 1,1,2-trifluoro-2-chloro-2-iodoethyl phenyl ether, are prepared by reacting an alkoxide or phenoxide with a 1,1-difluoro-1,2-dihaloethane (with the proviso that halo is not fluoro and at least one of the halo substituents is bromo or iodo) in an organic solvent at temperatures ranging from about -30.degree. C. to about 100.degree. C. These compounds may be dehalogenated with zinc to form the corresponding vinyl ethers.The reaction of halogen derivatives of fluorocarbons with nucleophiles is dramatically facilitated by a bromo or iodo substituent in the beta position.Type: GrantFiled: August 26, 1981Date of Patent: December 27, 1983Assignee: The Dow Chemical CompanyInventors: William P. Carl, Bobby R. Ezzell
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Patent number: 4385185Abstract: Compounds of the general formula I: ##STR1## wherein R.sub.1 and R.sub.2 are equal or different alkyl-, alkoxyalkyl-, or aryl groups, or together form a ring; R.sub.3 is an allyl or benzyl radical; and R.sub.4 and R.sub.5 represent hydrogen, alkyl, alkoxyalkyl, alkenyl or further compounds of the formula II: ##STR2## wherein R.sub.1, R.sub.2, R.sub.4 and R.sub.5 have the meaning indicated above and R.sub.6 stands for hydrogen or methyl or to compounds which are modified by the addition of hydrogen to at least one olefinic or carbonylic double bond of compounds of the general formula I or II. The invention also relates to a process for preparing the new compounds. The compounds of the general formula II are obtained by thermal treatment of a selection of compounds of formula I, for which R.sub.3 stands for the allyl or methallyl radical. The compounds according to the invention are used as fragrant and flavoring substances.Type: GrantFiled: March 20, 1981Date of Patent: May 24, 1983Assignee: Consortium fur Elektrochemische Industrie GmbHInventors: Helmut Gebauer, Walter Hafner
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Patent number: 4365097Abstract: Processes for the preparation of certain halogenated aliphatic ethers are described, and in particular the preparation of 1,1,2-trifluoro-2-chloroethyl methyl ether, i.e., CH.sub.3 OCF.sub.2 CHFCl. This particular ether has many uses, and is a valuable material for use in the production of the inhalant anesthetic enflurane, 1,1,2-trifluoro-2-chloroethyl difluoromethyl ether, i.e., CF.sub.2 HOCF.sub.2 CHFCl, made and sold under the trademark ETHRANE by Airco, Inc., Montvale, New Jersey 07645.Type: GrantFiled: March 16, 1981Date of Patent: December 21, 1982Assignee: Airco, Inc.Inventors: Ross C. Terrell, Kirsten Hansen
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Patent number: 4346246Abstract: Process for adjusting the halogen content of halogenated aliphatic ethers, by selective replacement of a halide substituent on the ether with a hydrogen. The process is particularly useful for the production of certain inhalant anesthetics.Type: GrantFiled: May 13, 1980Date of Patent: August 24, 1982Assignee: Airco, Inc.Inventors: Ross C. Terrell, Kirsten Hansen
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Patent number: 4340750Abstract: A fluorovinyl ether having the formulaXRfCF.sub.2 OCF.dbd.CF.sub.2 (I)wherein X represents --H, --Cl, --Br, --F, --CO.sub.2 R, --CONRR', --SO.sub.2 F, ##STR1## or --COF and R represents a C.sub.1 -C.sub.10 alkyl group; R' represents --H or a C.sub.1 -C.sub.10 alkyl group; Rf represents a C.sub.1 -C.sub.20 bifunctional perfluoro-containing group is produced by reacting an iodine-containing ether having the formulaXRfCF.sub.2 OCF.sub.2 CF.sub.2 I (II)in the presence of a catalytic component selected from the group consisting of Mg, Cu, Zn, Zn-Cu, Zn-Cd, Zn-Pd, Zn-Hg, Sn, Sb, organomagnesium compounds and organolithium compounds.Type: GrantFiled: October 29, 1980Date of Patent: July 20, 1982Assignee: Asahi Glass Company, Ltd.Inventors: Masaaki Yamabe, Seisaku Kumai, Seiji Munekata
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Patent number: 4334105Abstract: Methods for the dehalogenation of various haloethers are disclosed, comprising providing a haloether having the formula CX'.sub.3 -[CY.sub.2 ].sub.n -O-CZ.sub.2 -CX.sub.3 in which X', Y, Z and X are specifically disclosed combinations of hydrogen, fluorine chlorine and bromine such that the molecule includes at least one reducible group, but where both portions of any ethyl groups present are not reducible. Dehalogenation of these haloethers is carried out by contacting same with a hydrogen donor comprising an amine, preferably a primary or secondary amine or a primary, secondary or tertiary alkanol amine. The amine is preferably used in combination with a catalyst, such as a varivalent metal or a salt thereof, such as copper or a copper salt.Type: GrantFiled: August 8, 1980Date of Patent: June 8, 1982Assignee: Airco, Inc.Inventors: Ross C. Terrell, Kirsten Hansen
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Patent number: 4314087Abstract: Hexafluoropropylene may be conventionally oxidized to form an impure mixture comprising hexafluoroacetone and residual hexafluoropropylene, which materials are separable only with difficulty. The impure mixture may be subjected to reducing conditions to hydrogenate the hexafluoroacetone to a hexafluoroisopropanol product, which product is easily separable from the hexafluoropropylene impurity, which impurity may be recycled for further oxygenation and production of the acetone. Alternatively, hexafluoroisopropanol may be conventionally made from hexachloroacetone to form an impure mixture of hexafluoroacetone and HF. When this impure mixture is hydrogenated, the resulting hexafluoroisopropanol, mixed with hydrogen fluoride, is formed. Either of these alcohol products may be reacted with hydrogen fluoride and a formaldehyde to obtain a fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether, which is a useful anesthetic.Type: GrantFiled: December 26, 1979Date of Patent: February 2, 1982Assignee: Baxter Travenol Laboratories, Inc.Inventor: Phillip C. Radlick
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Patent number: 4292449Abstract: The reaction of a polyfluorocarbonyl compound such as a polyfluoroketone or polyfluorocarboxylic acid fluoride with fluoride ion and a polyfluoroallyl chloride, bromide or fluorosulfate produces a polyfluoroallyloxy compound, e.g., CF.sub.2 .dbd.CFCF.sub.2 OCF.sub.2 CF.sub.3. The polyfluoroallyloxy compounds copolymerize with ethylenically unsaturated monomers such as tetrafluoroethylene, chlorotrifluoroethylene or vinylidene fluoride to form polymers which are moldable, and in some cases electrically conducting or are water-wettable and dyeable.Type: GrantFiled: May 1, 1980Date of Patent: September 29, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: Carl G. Krespan