Alicyclic Ring And Halogen Containing Patents (Class 568/669)
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Patent number: 5354901Abstract: Perfluoro(cycloaliphatic methyleneoxyalkylene) compositions are provided. These compositions comprise perfluoro(cycloaliphatic methyleneoxyalkylene) carbonyl fluoride compounds having (a) a perfluorocycloaliphatic moiety which can have up to two perfluoroalkyl substituents and a perfluoroalkylene substituent, and (b) a perfluoromethyleneoxyalkylene carbonyl fluoride radical, the methylene group of the radical being bonded to a ring carbon atom or the perfluoroalkylene substituent of the moiety and the alkylene group of the perfluoromethyleneoxyalkylene carbonyl fluoride being a perfluoro(methyl)methylene group, a perfluoroisopropyleneoxy(methyl)methylene group, or a poly(perfluoroisopropyleneoxy)perfluoro(methyl)methylene group having up to about 10 perfluoroisopropyleneoxy units.Type: GrantFiled: February 1, 1993Date of Patent: October 11, 1994Assignee: Minnesota Mining and Manufacturing CompanyInventors: Richard M. Flynn, Patricia M. Savu
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Patent number: 5313003Abstract: A 2-allyl-perfluoroalkyl-trifluorovinyl ether of the formula ##STR1## wherein R.sup.1.sub.F and R.sup.2.sub.F represent either --CF.sub.3 or, together, (CF.sub.2).sub.n where n=2 or 3.Type: GrantFiled: June 10, 1993Date of Patent: May 17, 1994Assignee: Bayer AktiengesellschaftInventors: Ralf Kruger, Michael Negele, Albrecht Marhold
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Patent number: 5292961Abstract: Process for the preparation of halogenated polyethers of the general formula: ##STR1## wherein X=Cl or F, R.sub.F and R'.sub.F either equal to or different from each other, are selected from fluorinated alkyl radicals with from 1 to 20 carbon atoms, cycloalkyl, heterocyclic, alkylcycloalkyl or cycloalkylalkyl radicals, having from 5 to 20 carbon atoms, said radicals possibly containing also other halogen atoms different from fluorine and possibly ethereal oxygen atoms, by reaction with a fluoroxy or chloroxy compound of the formula: R'.sub.F OX with a fluorovinylether of the general formula: R.sub.F O--CF.dbd.CF.sub.2.Type: GrantFiled: June 4, 1993Date of Patent: March 8, 1994Assignee: Ausimont S.p.A.Inventors: Antonio Marraccini, Giovanni Gustalla, Alessandro Malacrida, Giorgio Guglielmo
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Patent number: 5288428Abstract: Compounds having a terminal alkyloxypropenyl group of the general formula ##STR1## wherein rings A.sup.1 and A.sup.2 each independently represent unsubstituted or halogen-substituted 1,4-phenylene, in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen, or trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl; n is either 0 or 1; Z.sup.1 and Z.sup.2 each independently signify a single covalent bond or --CH.sub.2 CH.sub.2 --, --COO--, --OOC--, --OCH.sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 O--, the trans form of --O--CH.sub.2 --CH.dbd.CH--, --CH.dbd.CH--CH.sub.2 --O--, --(CH.sub.2).sub.2 CH.dbd.CH-- or --CH.dbd.CH--(CH.sub.2).sub.2 --; R.sup.1 denotes an alkyl group; R.sup.2 represents halogen, cyano, trifluoroacetyl, optionally fluorine-substituted alkyl with 1 to 12 carbon atoms, in which optionally 1 --CH.sub.2 -- group or 2 non-adjacent --CH.sub.2 -- groups is/are replaced by oxygen and/or a --CH.sub.2 CH.sub.Type: GrantFiled: August 6, 1991Date of Patent: February 22, 1994Assignee: Hoffmann-La Roche Inc.Inventor: Stephen Kelly
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Patent number: 5225515Abstract: Polybenzazole polymers may contain perfluorocyclobutane rings to provide a flexible moiety which is stable at high temperatures.Type: GrantFiled: April 17, 1991Date of Patent: July 6, 1993Assignee: The Dow Chemical CompanyInventors: Zenon Lysenko, William J. Harris
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Patent number: 5210282Abstract: Perfluoro(cycloaliphatic methyleneoxyalkylene) compositions are provided. These compositions comprise perfluoro(cycloaliphatic methyleneoxyalkylene) carbonyl fluoride compounds having (a) a perfluorocycloaliphatic moiety which can have up to two perfluoroalkyl substituents and a perfluoroalkylene substituent, and (b) a perfluoromethyleneoxyalkylene carbonyl fluoride radical, the methylene group of the radical being bonded to a ring carbon atom or the perfluoroalkylene substituent of the moiety and the alkylene group of the perfluoromethyleneoxyalkylene carbonyl fluoride being a perfluoro(methyl)methylene group, a perfluoroisopropyleneoxy(methyl)methylene group, or a poly(perfluoroisopropyleneoxy)perfluoro(methyl)methylene group having up to about 10 perfluoroisopropyleneoxy units.Type: GrantFiled: June 30, 1992Date of Patent: May 11, 1993Assignee: Minnesota Mining and Manufacturing CompanyInventors: Richard M. Flynn, Patricia M. Savu
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Patent number: 5196569Abstract: Trifluorovinyl ethers containing selected functional groups, and homo- and copolymers prepared from them, are disclosed, as well as intermediates useful in the preparation of the ethers.Type: GrantFiled: October 10, 1991Date of Patent: March 23, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ming-Hong Hung
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Patent number: 5187286Type: GrantFiled: March 25, 1991Date of Patent: February 16, 1993Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Buchmann, Josef Heindl, Wolfgang Frohlich, Roland Ekerdt
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Patent number: 5183587Abstract: A liquid crystal compound having a relatively low viscosity, a superior compatibility with other liquid crystalline compounds and suitable for preparing a liquid crystal device having a high response rate, and a superior liquid crystal composition containing the compound are provided, which compound is expressed by the formula ##STR1## wherein R.sup.1 is H, F, Cl, CN or 1-20C alkyl or alkenyl in which alkenyl one --CH.sub.2 -- group or two not adjacent --CH.sub.2 -- groups may be replaced by --O-- and in which alkenyl the position and number of the double bond may be optionally chosen; A.sup.1, A.sup.2 and A.sup.3 are ##STR2## the H atom(s) of which ##STR3## may be replaced by F, Cl or methyl; B.sup.1 and B.sup.2 are --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 -- or single bond; n is 0 or 1; and m is 0 to 20.Type: GrantFiled: December 22, 1989Date of Patent: February 2, 1993Assignee: Chisso CorporationInventors: Kisei Kitano, Makoto Ushioda, Manabu Uchida, Toshiharu Suzuki
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Patent number: 5117055Abstract: A perfluoroalkyl halogenide represented by the formula: ##STR1## wherein X stands for one element selected from the group consisting of iodine and bromine, R.sub.f for a perfluorohydrocarbon group, n for an integer in the range of 1 to 3, and m for an integer in the range of 1 to 3, provided that n and m satisfy the relationship, n.gtoreq.m, is produced by a method which consists essentially in subjecting a perfluorocarboxylic acid fluoride represented by the formula, ##STR2## wherein R.sub.f and n have the same meanings as defined above, to a thermal reaction with a lithium halogenide represented by XI, wherein X has the same meaning as defined above.Type: GrantFiled: February 22, 1990Date of Patent: May 26, 1992Assignees: Agency of Industrial Science and Technology, Ministry of International Trade & IndustryInventors: Takashi Abe, Eiji Hayashi, Haruhiko Fukaya
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Patent number: 5105022Abstract: Dialkoxyethenes of the formula ##STR1## where R.sup.1 to R.sup.4 are identical or different and are each straight-chain or branched alkyl or cycloalkyl or R.sup.2 and R.sup.3 may furthermore be hydrogen, aryl or alkenylaryl, and the aromatic may be substituted by further radicals, such as alkyl, alkoxy or halogens, are prepared by a process in which an alcohol of the formula R.sup.4 OH or R.sup.5 OH is eliminated from a trialkoxyethane of the formula (II) ##STR2## where R.sup.1 to R.sup.4 have the above meanings and R.sup.5 is straight-chain or branched alkyl or cycloalkyl, in the presence of a zeolite and/or a phosphate and/or phosphoric acid or boric acid on a carrier and/or an acidic, untreated metal oxide as a catalyst. Zeolites of the pentasil type are preferably used as catalysts.Type: GrantFiled: September 11, 1990Date of Patent: April 14, 1992Assignee: BASF AktiengesellschaftInventors: Wolfgang Holderich, KoDieter, Werner Bertleff
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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: 5066746Abstract: The present invention is a process for preparing a polymer having perfluorocyclobutane rings by the steps of (a) contacting monomers having at least two dimerizable perfluorovinyl groups; and (b) exposing the monomers to sufficient heat and for a sufficient time that a polymer containing perfluorocyclobutane rings is formed wherein at least about 0.05 mole percent of the monomer, have at least 3 dimerizable perfluorovinyl groups and polymers prepared thereby.Type: GrantFiled: June 7, 1990Date of Patent: November 19, 1991Assignee: The Dow Chemical CompanyInventors: Katherine S. Clement, David A. Babb, Bobby R. Ezzell
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Patent number: 5064564Abstract: The present invention discloses an optically active compound represented by the following general formula (I): ##STR1## wherein R.sup.1 represents an alkyl, alkoxyl, or alkoxyalkanoyloxy group which has 1 to 18 carbon atoms and may be substituted with fluorine, chlorine, or cyano group; R.sup.2 represents an alkyl group having 1 to 18 carbon atoms; ##STR2## m is 0 or 1; Y represents a single bond, --CH.sub.2 O--, or --COO--; Z represents a single bond or --COO--; and C* and C** each independently represents an asymmetric carbon atom of the (R) and (S) configuration, an intermediate therefor being represented by the following general formula (II): ##STR3## wherein R.sup.2 represents an alkyl group having 1 to 18 carbon atoms, n is 0 or 1, and C* and C** each independently represents an asymmetric carbon atom of the (R) or (S) configuration, a process for producing the intermediate, and a liquid-crystal compound using the optically active compound.Type: GrantFiled: December 20, 1990Date of Patent: November 12, 1991Assignees: Dainippon Ink and Chemicals, Inc., Sagami Chemical Research CenterInventors: Sadao Takehara, Takeshi Kuriyama, Toru Fujisawa, Kayoko Nakamura, Tamejiro Hiyama, Kusumoto, Tetsuo, Akiko Nakayama
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Patent number: 5037919Abstract: A compound having at least one perfluorovinyl group and at least one functional group is suitable for reacting with and/or forming polymers. The compound is preferably of Formula I:(G)n--R--(X--CF.dbd.CF.sub.2).sub.mwherein R represents an optionally substituted hydrocarbyl group, X represents any group which links R and a perfluorovinyl group; n is the number of G groups, m is the number of (XCF.dbd.CF.sub.2) groups; and G represents any reactive functional group of a group convertible into a reactive functional groups.A process for preparing a compound of Formula I comprises the steps of:(a) preparing a 2-halotetrafluoro compound of the formula III:(Q--CF.sub.2 --CF.sub.2 X).sub.m --R--(G").sub.Type: GrantFiled: June 9, 1989Date of Patent: August 6, 1991Assignee: The Dow Chemical CompanyInventors: Katherine S. Clement, Bobby R. Ezzell, David A. Babb, W. Frank Richey
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Patent number: 5037917Abstract: A process for preparing a polymer having perfluorocyclobutane rings by the steps of (a) contacting monomers having at least two dimerizable perfluorovinyl groups; and (b) exposing the monomers to sufficient heat and for a sufficient time that a polymer containing perfluorocyclobutane rings is formed. The invention includes polymers having a backbone comprising hydrocarbyl groups, perfluorocyclobutane rings and non-carbon atoms and polymers of at least 10,000 molecular weight having repeating units [O-(CFR.sub.f).sub.n -O-perfluorocyclobutane].Type: GrantFiled: June 9, 1989Date of Patent: August 6, 1991Assignee: The Dow Chemical CompanyInventors: David A. Babb, Katherine S. Clement, W. Frank Richey, Bobby R. Ezzell
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Patent number: 5037918Abstract: A crosslinked polymer having perfluorocyclobutane rings is prepared in a process comprising the steps of: (a) contacting monomers having two dimerizable perfluorovinyl groups; (b) exposing the monomers to sufficient heat and for a sufficient time that a (linear) polymer containing perfluorocyclobutane rings is formed; and (c) exposing the polymer to sufficient crosslinking initiating means and for a sufficient time such that crosslinking occurs. Crosslinked polymers, so prepared are novel and have tensile strength and other physical proeprties enhanced over the properties of the corresponding linear polymer.Type: GrantFiled: December 15, 1989Date of Patent: August 6, 1991Assignee: The Dow Chemical CompanyInventor: David A. Babb
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Patent number: 5023380Abstract: Compounds have a structure represented by Formula I:CF.sub.2 =CF-X-R-(X-CF=CF.sub.2).sub.mwherein R represents an unsubstituted or inertly substituted hydrocarbyl group; each X is independently selected from the group consisting of groups having at least one non-carbon atom between R and --CF=CF.sub.2 ; and m is an integer of from 1 to about 3. Polymers formed from such compounds are also prepared. The compounds are preferably prepared by a method by a process comprising the steps of:(a) forming a salt having anion corresponding to a compound of Formula II:HX--R--(XH).sub.m ;wherein X, R and m are as defined for Formula I;(b) reacting the salt with a 1,2-dihalo-1,1,2, 2-tetrafluoroethane wherein the halo groups are iodine, bromine, chlorine or mixtures thereof, at least one halo group being bromine or iodine, to form a compound of Formula III:Z-CF.sub.2 CF.sub.2 -X-R-(X-CF.sub.2 CF.sub.2 - Z).sub.Type: GrantFiled: June 9, 1989Date of Patent: June 11, 1991Assignee: The Dow Chemical CompanyInventors: David A. Babb, Bobby R. Ezzell, Katherine S. Clement
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Patent number: 5021602Abstract: Novel compounds have at least one perfluorocyclobutane ring and at least two functional groups suitable for forming condensation polymers. Preferably the compounds have a structures represented by Formula II: ##STR1## wherein R and R' independently represent optionally inertly substituted groups; X and X' represent any molecular structures which link R and R' with the perfluorocyclobutane ring; n and n' are the number of G and G' groups, respectively; and G and G' independently represent any reactive functional groups or any groups convertible into reactive functional groups. The compound are preferably prepared by a process of thermally dimerizing trifluorovinyl compound to form a compounds of Formula IG.sub.n --R--X--CF.dbd.CF.sub.2wherein G represents G or G' in Formula II; X represents X or X' of Formual II; and n represents n or n' of Formula II, to form a compound having a perfluorocyclobutane group.Type: GrantFiled: June 9, 1989Date of Patent: June 4, 1991Assignee: The Dow Chemical CompanyInventors: Katherine S. Clement, David A. Babb, Bobby R. Ezzell
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Patent number: 4983630Abstract: There are provided new 2,2-difluorocyclopropylethane derivatives of general formula I ##STR1## in which A, B and R.sup.1-5 have the meanings given in the description and processes for their preparation. The compounds of the invention can be used as pesticides, especially against insects and mites.Type: GrantFiled: November 28, 1988Date of Patent: January 8, 1991Assignee: Schering AktiengesellschaftInventors: Peter Wegner, Hartmut Joppien, Gunter Homberger, Arnim Kohn
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Patent number: 4978806Abstract: A method for preparation of 1-methoxycyclohepta-1,3,5-triene in commercial quantities, which comprises the steps of heating 7,7-dichloro-1-methoxybicyclo[4.1.0]heptane in a refluxing reaction solvent comprising a lower boiling aromatic amine, at reflux, until suitable amounts of 1-methoxycyclohepta-1,3,5-triene have been produced, and recovering the 1-methoxycyclohepta-1,3,5-triene. Suitable reaction solvents include 2-picoline, pyridine and 2,6-lutidine. The method according to the present invention results in safer temperature control in the production of 1-methoxycyclohepta-1,3,5-triene, and increased yields.Type: GrantFiled: November 27, 1989Date of Patent: December 18, 1990Assignee: Her Majesty the Queen in right of Canada, as represented by the Minister of National Defence of Her Majesty's Canadian GovernmentInventor: Gordon E. Langford
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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: 4960951Abstract: Novel perfluoropolyethers, such as perfluorodipentaerythritol hexaethyl ether, and their intermediates exhibit excellent chemical and thermal stability and are useful as vapor phase soldering fluids and convection cooling liquids.Type: GrantFiled: February 14, 1990Date of Patent: October 2, 1990Assignee: E. I. Du Pont de Nemours and CompanyInventors: Mario J. Nappa, Allen C. Sievert, Walter R. Tong
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Patent number: 4937390Abstract: The present invention relates to the use of the compound D-3-deoxy-3-fluoro-4-O-methyl-myo-inositol for the synthesis of D-3-deoxy-3-fluoro-myo-inositol.Type: GrantFiled: February 3, 1989Date of Patent: June 26, 1990Assignee: University of PittsburghInventor: Abdul H. Faug
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Patent number: 4935560Abstract: Novel styryl-tetrahydromaphthalene and indane derivatives useful for treating neoplasms and dermatoses.Type: GrantFiled: January 16, 1990Date of Patent: June 19, 1990Assignee: Hoffmann-La Roche Inc.Inventors: Michael Klaus, Peter Loeliger, Peter Mohr, Ekkehard Weiss
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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: 4867903Abstract: A fluoroalkane derivative represented by the formula: ##STR1## wherein R denotes an alkyl group having 1-16 carbon atoms, C* denotes an asymmetric carbon atom, R.sup.1 denotes an alkyl or alkoxy group having 1-16 carbon atoms; ##STR2## respectively denote a phenylene group ##STR3## a cyclohexylene group ##STR4## or a pyrimidinylene group ##STR5## p is 0 or 1, q is 0 or 1 when p is 1, r is 0 or 1; and l, m and n are respectively 0 or a positive integer satisfying the relationship of l+m+n.gtoreq.1. The fluoroalkane derivative has a fluorine atom providing a large dipole moment and directly connected to an asymmetric carbon atom, so that it provides a high speed responsive characteristic through an increased spontaneous polarization when contained in a liquid crystal composition, especially a ferroelectric liquid crystal composition.Type: GrantFiled: March 6, 1987Date of Patent: September 19, 1989Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Masanao Kamei, Shinichi Nakamura, Kazuharu Katagiri
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Patent number: 4868318Abstract: The present invention relates to novel perfluoro chemicals (PFC), particularly perfluorocyclic ethers and polyfluorinated compounds containing a few chlorine atoms and to a method for the preparation thereof.Type: GrantFiled: March 9, 1987Date of Patent: September 19, 1989Assignee: The Green Cross CorporationInventors: Kirby V. Scherer, Jr., Taizo Ono, Kouichi Yamanouchi, Kazumasa Yokoyama
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Patent number: 4762952Abstract: A perfluorosulphonic acid polymer suitable for use as a catalyst contains units of the formula:[(SO.sub.3).sub.w M(SO.sub.3 R).sub.z-w ] (I)whereinM is a multivalent metal cation,R is a C.sub.1 to C.sub.8 fluorinated alkyl group,z is the valency of M, andw is an integer having a value between 1 and z-1.Also use of a polymer of formula (I) wherein M is aluminum as a catalyst in the production of glycol ethers by the reaction of an alkylene oxide and an alcohol.Type: GrantFiled: March 10, 1987Date of Patent: August 9, 1988Assignee: BP Chemicals LimitedInventor: Michael J. Green
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Patent number: 4714785Abstract: Organic haloformate, e.g., chloroformate, compounds are converted to their corresponding halides, e.g., chlorides, by heating the haloformate, e.g., between 90.degree. C. and 150.degree. C., in the presence of a catalytic amount of a carbon catalyst for a time sufficient to convert the haloformate to the corresponding halide.Type: GrantFiled: September 15, 1986Date of Patent: December 22, 1987Assignee: PPG Industries, Inc.Inventor: James A. Manner
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Patent number: 4642392Abstract: A process for the telomerization of a conjugated alkadiene with an alkanol is disclosed for the production of an organo-oxyalkadiene. A palladium catalyst having a phosphine or stibene ligand is employed in a substantially oxygen-free environment and in the presence of a high boiling solvent so that the reaction products may be separated from the catalyst by distillation. Vacuum fractional distillation is a preferred method for separating the products.Type: GrantFiled: September 30, 1985Date of Patent: February 10, 1987Assignee: National Distillers and Chemical CorporationInventor: Ronnie M. Hanes
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Patent number: 4627933Abstract: Compounds of the formulaR.sup.1 --Q.sup.1 --(CH.sub.2).sub.m --(COO).sub.n --(CH.sub.2).sub.p --Q.sup.2 --R.sup.2whereinR.sup.1 and R.sup.2 are each independently alkyl or alkoxy each of 1-12 C atoms, F, Cl, Br, CN or --Q.sup.3 --R.sup.3, or one of R.sup.1 and R.sup.2 can also be H;Q.sup.1, Q.sup.2 and Q.sup.3 are each independently 1,4-phenylene, 1,4-cyclohexylene, 1,4-bicyclo(2,2,2)-octylene or 1,3-dioxane-2,5-diyl, each of which is unsubstituted or substituted by 1-4 fluorine, chlorine or bromine atoms;R.sup.3 is alkyl or alkoxy each of 1-8 C atoms, H, F, Cl, Br or CN;m is 1, 2, 3, 4, 5 or 6; n is 0 or 1; and p is 0, 1, 2, 3, 4 or 5; the sum of (m+p) being 2, 4 or 6 and the sum of (m+n+p) being at least 3;but with the proviso that Q.sup.3 is unsubstituted 1,4-phenylene or 1,4-phenylene substituted by a fluorine, chlorine or bromine atom, only when n=1 or (m+p)=6 or at least one of R.sup.1 or R.sup.3 is F, Cl or Br or none of R.sup.1 to R.sup.3 is CN or two of the radicals R.sup.1 to R.sup.Type: GrantFiled: July 7, 1983Date of Patent: December 9, 1986Assignees: Merck Patent Gesellschaft mit beschrankter Haftung, The Secretary of State for Defense in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Rudolf Eidenschink, Joachim Krause, Beatrice M. Andrews, George W. Gray, Neil Carr
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Patent number: 4622163Abstract: New anisotropic compounds with a cross-polarizing substituent have the formula (1) ##STR1## The increase in .epsilon..perp. is achieved by the polarizing group X, preferably the cyano group or a halogen atom, which is not laterally on the ring, as with the known compounds, but is on the bridge, that is to say is part of the main bridge bonding rings A and B to one another. Ring A has the formula (1a) or (1b) given herein and is always cycloaliphatic, while ring B can be identical to ring A or is an aromatic ring of the formula (1c) or (1d) herein. R.sup.1 and R.sup.2 are identical or different end groups of the formula (1e) herein. The radical X on the bridge causes less widening of the molecule than a radical X on a ring, which provides comparatively higher clear points and moreover enables aromatic rings to be omitted from the anisotropic compounds.Type: GrantFiled: September 10, 1984Date of Patent: November 11, 1986Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Tuong Huynh-Ba, Maged A. Osman
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Patent number: 4622431Abstract: Organic chloroformate compounds are decomposed to their corresponding chlorides by heating the chloroformate, e.g., between 100.degree. and 175.degree. C., in the presence of a catalytic amount of solid poly(vinylpyridine), e.g., poly(4-vinylpyridine), for a time sufficient to convert the chloroformate to the corresponding chloride.Type: GrantFiled: April 4, 1985Date of Patent: November 11, 1986Assignee: PPG Industries, Inc.Inventors: Robert G. Briody, Henry C. Stevens
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Patent number: 4605786Abstract: A perfluoroether compound having the following formula is useful as a thermostable, inert solvent and inter alia as an oxygen carrier in an artificial blood or infusion fluid. ##STR1## wherein Rf.sub.1 and Rf.sub.2 are different from each other and are selected from the group of a C.sub.1 or C.sub.3 perfluoroalkyl group which may be interrupted by an oxygen atom, and a C.sub.5 -C.sub.7 perfluorocycloalkyl group, and n and n' are zero or an integer of 1; one of Rf.sub.1 and Rf.sub.2 being the C.sub.5 -C.sub.7 perfluorocycloalkyl group and the total number of carbon atoms being 9-11 inclusive.Type: GrantFiled: December 20, 1983Date of Patent: August 12, 1986Assignee: The Green Cross CorporationInventors: Kazumasa Yokoyama, Yoshihisa Inoue, Taizo Ono, Chikara Fukaya, Yoshio Arakawa, Youichiro Naito, Koichi Yamauchi, Tadakazu Suyama
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Patent number: 4575517Abstract: Cyclopropylmethyl(ene) ethers have an outstanding action in microbicidal agents for preserving industrial materials from damage or destruction by microorganisms.Type: GrantFiled: February 16, 1984Date of Patent: March 11, 1986Assignee: Bayer AktiengesellschaftInventors: Bernd-Wieland Kruger, Uwe Priesnitz, Gerhard Jager, Wilfried Paulus, Hermann Genth
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Patent number: 4575516Abstract: Substituted cyclopropylmethyl(ene) ethers of the formula ##STR1## in which X.sup.1 and X.sup.2 are identical or different and represent halogen,R.sup.1 represents hydrogen or alkyl,R.sup.2 and R.sup.3 are identical or different and represent hydrogen, alkyl, optionally substituted aryl, halogenoalkyl, hetero-alkyl, alkoxyalkyl, alkylthioalkyl, optionally substituted alkenoxyalkyl, optionally substituted alkinoxyalkyl or (di)alkylaminoalkyl,R.sup.4 represents hydrogen or alkyl,R.sup.5 and R.sup.6 are identical or different and represent hydrogen or optionally substituted radicals from the series comprising alkyl, aryl and aralkyl andR represents a trihalogenoalkenyl, alkinyl or iodoalkinyl radical,exhibit some arthropodicidal activity and synergize other known arthropodicides.Type: GrantFiled: February 1, 1984Date of Patent: March 11, 1986Assignee: Bayer AktiengesellschaftInventors: Bernd-Wieland Kruger, Uwe Priesnitz, Gerhard Jager, Wolfgang Behrenz
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Patent number: 4565859Abstract: A polyether compound having ether groups and vinyl double bonds represented by formula (I) ##STR1## wherein R.sub.1 represents a residue of an organic compound having l active hydrogen atoms, n.sub.1 through n.sub.l each represents 0 or an integer of from 1 to 100, the sum of the integers represented by n.sub.1 through n.sub.l is from 1 to 100, andl represents an integer of from 1 to 100, and A represents ##STR2## and a process for production thereof; an epoxy resin represented by formula (II) ##STR3## wherein R.sub.1 and n.sub.1 through n.sub.l are defined above, and B is an oxycyclohexane unit having a substituent and is represented by formula (III) ##STR4## wherein X represents a ##STR5## --CH.dbd.CH.sub.2, or ##STR6## groups, wherein R.sub.Type: GrantFiled: January 29, 1985Date of Patent: January 21, 1986Assignee: Daicel Chemical Industries, Ltd.Inventors: Takaaki Murai, Shoji Watanabe, Kimio Inoue, Toyokazu Yagii
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Patent number: 4526999Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are inhibitors of leukotriene biosynthesis. These compounds inhibit lipoxygenase, thus preventing the metabolism of arachidonic acid to the leukotrienes. These compounds are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders.Type: GrantFiled: April 25, 1983Date of Patent: July 2, 1985Assignee: Merck & Co., Inc.Inventors: Philippe L. Durette, Timothy F. Gallagher
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Patent number: 4487953Abstract: Compounds of Formula (I) ##STR1## wherein the 9-bromine atom can be in the .alpha.- or .beta.-position,R.sub.1 is CH.sub.2 OH or C(O)OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is C(O)NHR.sub.3 wherein R.sub.3 is an acid residue or R.sub.2 ; andA is --CH.sub.2 --CH.sub.2 -- or cis --CH.dbd.CH--;B is --CH.sub.2 --CH.sub.2 --, trans --CH.dbd.CH--, or --C.tbd.C--;W is a free or functionally modified hydroxymethylene group or a free or functionally modified ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position; D and E together are a direct bond; orD is straight-chain, branched, or cyclic alkylene of 1-10 carbon atoms, optionally substituted by fluorine atoms; andE is oxygen, sulfur, a direct bond --C.tbd.C--, or --CR.sub.6 .dbd.CR.sub.7 --, wherein R.sub.6 and R.sub.7 are different from each other and each is hydrogen, chlorine, or C.sub.1 -C.sub.4 -alkyl;R.sub.4 is a free or functionally modified hydroxy group;R.sub.Type: GrantFiled: December 6, 1982Date of Patent: December 11, 1984Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger
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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: 4396782Abstract: A process for producing .alpha.,.beta.-unsaturated alkenyl ethers by cleavage of acetals in the gas phase and in the presence of a catalyst, the catalyst used being calcium oxide, the acetal cleavage being performed in the temperature range of 200.degree. to 300.degree. C. and the process being carried out preferably in a simple distilling apparatus.Type: GrantFiled: January 7, 1982Date of Patent: August 2, 1983Assignee: Ciba-Geigy CorporationInventors: Sameer H. Eldin, Milos Rusek
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Patent number: 4393248Abstract: A flame retardant, halogenated polyol having the formula ##STR1## wherein R is an aliphatic radical substituted with at least 1 hydroxyl groups, X is a halogen, and X' is a halogen or hydrogen, is used in the reaction mixture for preparing flame retarded polyurethanes.Type: GrantFiled: August 20, 1981Date of Patent: July 12, 1983Assignee: Pennwalt CorporationInventors: Stanley R. Sandler, Joseph M. Bohen
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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: 4371717Abstract: The present invention is directed to a process for the preparation of certain N-substituted-2-haloacetanilides via the reaction of a secondary 2-haloacetanilide with a haloalkyl ether, particularly, halomethyl ethers, which comprises forming the ether in situ by the in-solvent reaction of an alcohol, formaldehyde or other aldehyde and an acid halide to produce high purity haloalkyl ethers, while decreasing the concentration of undesirable bis by products, as for example bis(chloromethyl) ether. The ether formed in situ thereafter reacts with the secondary 2-haloacetanilide in the presence of a phase transfer catalyst and base to form the N-substituted-2-haloacetanilide.Type: GrantFiled: February 3, 1981Date of Patent: February 1, 1983Assignee: Monsanto CompanyInventors: Gerhard H. Alt, John P. Chupp
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Patent number: 4310709Abstract: The process for the manufacture of but-2-en-1-ol compounds by isomerizing but-3-en-1-ol compounds in the presence of a palladium catalyst and of hydrogen is improved by modifying the palladium catalyst with selenium or tellurium.The but-2-en-1-ols manufactured according to the invention are either solvents or valuable starting materials for the manufacture of solvents, dyes, surface coatings, paints and pesticides.Type: GrantFiled: April 23, 1980Date of Patent: January 12, 1982Assignee: BASF AktiengesellschaftInventor: Walter Rebafka
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Patent number: 4310700Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation enhibitors and bronchodilators.Type: GrantFiled: April 3, 1980Date of Patent: January 12, 1982Assignee: American Cyanamid CompanyInventors: Allan Wissner, Middleton B. Floyd, Jr.
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Patent number: 4297366Abstract: 2,2-Dimethyl-3-(2-fluoroalkyl-2-oxy-vinyl)-cyclopropane-carboxylic acid esters of the formula ##STR1## in which R.sup.1 is fluoroalkyl,R.sup.2 is an optionally substituted alkyl, cycloalkyl, aralkyl or aryl radical, andR.sup.3 is a radical customary in the alcohol component of pyrethroidswhich possess arthropodicidal properties. New intermediates therefor are also shown.Type: GrantFiled: April 23, 1980Date of Patent: October 27, 1981Assignee: Bayer AktiengesellschaftInventors: Rainer Fuchs, Ingeborg Hammann, Bernhard Homeyer, Wolfgang Behrenz, Wilhelm Stendel
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Patent number: 4291174Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation inhibitors and bronchodilators.Type: GrantFiled: April 3, 1980Date of Patent: September 22, 1981Assignee: American Cyanamid CompanyInventors: Allan Wissner, Middleton B. Floyd, Jr.