Halogen In Acid Moiety Patents (Class 560/184)
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Patent number: 5324852Abstract: The present invention provides an optically active 4-substituted-2-hydroxybutanoate represented by the general formula: ##STR1## wherein X is Cl, Br, I or Cn, R is alkyl, and * shows an asymmetric carbon.The compounds which are useful as starting materials for medical agents, are obtained by a process comprising ring-opening optically active .alpha.-hydroxy-.gamma.-butyrolactone and esterifying the compound obtained.Type: GrantFiled: November 16, 1992Date of Patent: June 28, 1994Assignee: Chisso CorporationInventors: Naoyuki Yoshida, Kazutoshi Miyazawa
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Patent number: 5318769Abstract: Disclosed are contrast agents of the formula ##STR1## contained in aqueous compositions and methods for their use in diagnostic radiology of the gastrointestinal tract whereinX= ##STR2## Z=H, halo, C.sub.1 -C.sub.20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups;R=C.sub.1 -C.sub.25 alkyl, cycloalkyl, aryl, or halo-lower-alkyl, optionally substituted with halo, fluoro-lower-alkyl, lower-alkoxy, hydroxy, carboxy or lower-alkoxy carbonyl, lower-alkenyl, lower-alkynyl, lower-alkylene, lower-alkoxy-carbonyloxy;n=1-5;y=0-4; andw=1-4in an aqueous pharmaceutically acceptable carrier.Type: GrantFiled: March 31, 1993Date of Patent: June 7, 1994Assignee: Sterling Winthrop Inc.Inventors: Edward R. Bacon, Sol J. Daum, Kimberly G. Estep, Kurt A. Josef, Brent D. Douty, Carl R. Illig
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Patent number: 5279764Abstract: The invention relates to dihalogenobenzene derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --(Z.sup.2 --A.sup.3).sub.n --R.sup.2wherein R.sup.1, R.sup.2, A.sup.1, A.sup.2, A.sup.3, Z.sup.1, Z.sup.2 and n are as defined in the specification.Type: GrantFiled: November 23, 1992Date of Patent: January 18, 1994Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Volker Reiffenrath, Joachim Krause, Georg Weber, Ulrich Finkenzeller, Andreas Wachtler, Thomas Geelhaar, David Coates, Ian C. Sage, Simon Greenfield
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Patent number: 5274179Abstract: Photoinitiators having at least one terminal fluoroalkyl moiety are useful for photopolymerizing and photocuring fluorinated as well as non-fluorinated monomers, especially fluorinated acrylic monomers.Type: GrantFiled: April 6, 1993Date of Patent: December 28, 1993Assignee: AlliedSignal Inc.Inventor: Chengjiu Wu
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Patent number: 5274180Abstract: Esters of hydroxy terminated monofunctional polyalkylene oxide derivatives and monofunctional perfluoropolyether carboxylic acids are novel compounds. They may be used to form emulsions and to modify droplet size in atomization.Type: GrantFiled: October 22, 1992Date of Patent: December 28, 1993Assignee: British Petroleum Company plcInventor: David Masheder
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Patent number: 5264151Abstract: Disclosed herein are optically active phenols of formula (V) which are useful as precursors for esters used in liquid crystalline crystalline mixtures: ##STR1## wherein R.sub.2 represents an optically active alkyl or alkoxyalkyl group having 3 to 15 carbon atoms optionally substituted by halogen atoms; k represents a number of 0 or 1; n represents a number of 1 to 6.Type: GrantFiled: March 20, 1992Date of Patent: November 23, 1993Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Higashi, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Takeshi Tani, Chizu Kawakami, Koichi Fujisawa, Kiyoshi Imamura
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Patent number: 5258547Abstract: A process for preparing halogenated compounds of formula RCY(Z)CH.sub.2 CH(X)C(CH.sub.3)CH.sub.2 COR.sup.1 where X, Y and Z are halo, R is alkyl, halo, haloalkyl or aryl, and R.sup.1 is hydroxy, halo, alkoxy, alkyl or haloalkyl, or the residue of a pyrethroidal alcohol, in which a compound of formula CH.sub.2 =CHC(CH.sub.3).sub.2 COR.sup.1 is reacted with a sulphonyl halide of formula RCY(Z)SO.sub.2 X. The process avoids the use of volatile halocarbons in the production of valuable intermediates for insecticides.Type: GrantFiled: January 9, 1992Date of Patent: November 2, 1993Assignee: Imperial Chemical Industries plcInventor: Gary N. Sheldrake
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Patent number: 5235094Abstract: A halogenated ester is prepared by addition of a halogenated nucleophile to a diester at a temperature less than 15.degree. C. but greater than -25.degree. C.Type: GrantFiled: December 11, 1991Date of Patent: August 10, 1993Assignee: The Dow Chemical CompanyInventors: Kevin P. Darst, Marius W. Sorenson
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Patent number: 5227516Abstract: A fluorine-containing polyether of the formula:R.sub.f --X--A (I)orA--X--R'.sub.f --X--A (II)wherein R.sub.f and R'.sub.f are each a linear group containing a perfluoroalkyl polyether group, X is --CF.sub.2 COO--, --C.sub.2 F.sub.4 COO-- or --CF.sub.2 CF.sub.2 -- and A is a group containing a polyalkylene glycol group. The polyether can be used as a nonionic surfactant which is compatible with a perfluoroalkyl polyether.Type: GrantFiled: December 18, 1991Date of Patent: July 13, 1993Assignee: Daikin Industries Ltd.Inventors: Takashi Tohzuka, Sueyoshi Ishikawa, Ikuo Yamamoto
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Patent number: 5196543Abstract: The derivatives of the formula: ##STR1## wherein: R.sub.1 is H or C.sub.1 -C.sub.4 alkyl;X is either an oxygen atom, in which case R.sub.2 =H or halogen, or a methylene group or a --CH.dbd.CH-- group, in which case R.sub.2 =H;n is 1 or 2 when X is an oxygen atom or a methylene group and 0 or 1 when X is a --CH.dbd.CH-- group; each of R.sub.3 and R.sub.4 is independently H, C.sub.1 -C.sub.4 alkyl, C.sub.4 -C.sub.7 cycloalkyl, phenyl or benzyl;R.sub.5 is H or C.sub.1 -C.sub.4 alkyl;R.sub.6 is C.sub.1 -C.sub.4 alkyl, CHF.sub.2, CF.sub.3, CF.sub.3 CF.sub.2, C.sub.4 -C.sub.7 cycloalkyl, phenyl or benzyl;R.sub.4 and R.sub.6 may further form together a --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 --chain;R.sub.5 and R.sub.6 may further form together a --(CH.sub.2).sub.4 --or --(CH.sub.2).sub.5 --chain; andR.sub.7 is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.5 acyl or benzyl,useful as drugs, prepared by cyclizing N ethoxy carbonyl anilines with substituted 1, 3 dioxolane-2-ones.Type: GrantFiled: July 19, 1991Date of Patent: March 23, 1993Assignee: Delalande S.A.Inventors: Francois X. Jarreau, Vincenzo Rovei, Jean-Jacques Koenig, Alain R. Schoffs
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Patent number: 5153322Abstract: 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)perfluoro(methyl)methylene group having up to about 10 perfluoroisopropyleneoxy units. Also provided are functional derivatives of the perfluoro(cycloaliphatic methyleneoxyalkylene) carbonyl fluoride compounds and nonfunctional derivatives of the perfluoro(cycloaliphatic methyleneoxyalkylene) carbonyl fluoride compounds.Type: GrantFiled: October 10, 1989Date of Patent: October 6, 1992Assignee: Minnesota Mining and Manufacturing CompanyInventor: Richard M. Flynn
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Optically active fluorine-containing 3-hydroxybutyric acid esters and process for producing the same
Patent number: 5118836Abstract: An optically active (3R)- or (3S)-fluorine-containing-3-hydroxybutyric acid ester represented by the formula: ##STR1## wherein R represents an alkyl group of C.sub.3 -C.sub.16 and A represents CF.sub.3, CHF.sub.2 or CH.sub.2 F, which is useful for synthesis of optically active substances, is prepared with high optical purity by ester exchange reaction between an alcohol represented by the formula:ROHwherein R is as defined above and optically active (3R)- or (3S)-fluorine-containing-3-hydroxybutyric acid ethyl ester of ##STR2## in the presence of an ammonium salt of sulfonic acid.Type: GrantFiled: November 8, 1990Date of Patent: June 2, 1992Assignee: Showa Shell Sekiyu Kabushiki KaishaInventors: Kaichi Tanida, Yoshiichi Suzuki -
Patent number: 5113008Abstract: Hemiketals and hemithioketals are produced by bringing into reactive contact an alcohol or mercaptan and an oxetan-2-one compound having the following structural formula: ##STR1## where Hal is a halogen.Type: GrantFiled: January 22, 1991Date of Patent: May 12, 1992Assignee: Monsanto CompanyInventor: Mark J. Pozzo
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Patent number: 5102911Abstract: HMG-CoA reductase inhibitors of formulae (I) and (II) are disclosed.Type: GrantFiled: July 6, 1990Date of Patent: April 7, 1992Assignee: Merck & Co, Inc.Inventors: Ta J. Lee, Wilbur J. Holtz
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Patent number: 5099042Abstract: Polymers are produced from 4 and 5 member cyclic ethers, which polymers have hydroxyl functionalities of 4.Type: GrantFiled: March 14, 1989Date of Patent: March 24, 1992Assignee: Thiokol CorporationInventors: Robert B. Wardle, Jerald C. Hinshaw
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Patent number: 5051530Abstract: There are provided novel ester derivatives represented by the following formula(I): ##STR1## wherein, R.sub.1 represents methyl, ethyl, isopropyl, t-butyl, or phenyl; R.sub.2 represents phenyl, methoxy, ethoxy, isopropanoxy, or t-butanoxy; and X represents Br, and a process for preparing the same which comprises reacting an aldehyde of the formula (III) with an acid halide of the formula (IV) at 20.degree.-80.degree. C. in the presence or absence of solvents. ##STR2## Wherein, R.sub.1, R.sub.2 and X have the same meaning as defined above.Type: GrantFiled: January 16, 1990Date of Patent: September 24, 1991Assignee: Korea Institute of Science and TechnologyInventors: MoonHo Chang, Han-Young Kang, HunYeong Koh, YongSeo Cho, SangChul Shim
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Patent number: 5023362Abstract: Ketoester of the formula ##STR1## .alpha.-carboxylate-.omega.-acyl fluoride of the formula ##STR2## vinyl ether of the formula ##STR3## divinyl ether of the formula ##STR4## allyl ether of the formula ##STR5## and film-forming copolymers, useful as molding resins, of the vinyl ether and/or the divinyl ether or the allyl ether and a fluorinated vinyl monomer, for example, tetrafluoroethylene, wherein, in the above formulas, n is 0 to 6, p is 0 to 7, X is CO.sub.2 M, CO.sub.2 R, CO.sub.2 H, CONH.sub.2, COF, COCl or Cn, M is alkali metal, ammonium or quaternary ammonium and R is C.sub.1-8 alkyl, selected copolymers, after hydrolysis, being water-wettable and dyeable, exhibiting ion-exchange properties and being useful in curable fluoroelastomer compositions and, in film form, as the membrane in a chloroalkali electrolysis cell.Type: GrantFiled: June 19, 1987Date of Patent: June 11, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventor: Carl G. Krespan
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Patent number: 5021453Abstract: Compounds of formula (I) and (II): ##STR1## are HMG-CoA reductase inhibitors.Type: GrantFiled: June 6, 1990Date of Patent: June 4, 1991Assignee: Merck & Co., Inc.Inventors: Henry Joshua, Kenneth E. Wilson, Michael S. Schwartz, Ta J. Lee, Gerald E. Stokker
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Patent number: 5004554Abstract: A fluorine-containing polyether of the formula:R.sub.f.sup.1 CF.sub.2 CF.sub.2 COOR.sub.f.sup.2 (I)orR.sub.f.sup.2 OCO--CF.sub.2 CF.sub.2 R'.sub.f.sup.1 CF.sub.2 CF.sub.2 --COOR.sub.f.sup.2 (II)wherein R.sub.f.sup.1 and R'.sub.f.sup.1 are each a group containing a perfluoroalkyl polyether group, and R.sub.f.sup.2 is a fluorine-containing alkyl group or a fluorine-containing ether group, can be used as a lubricant which has good properties such as lubricity and durability properties.Type: GrantFiled: July 24, 1990Date of Patent: April 2, 1991Assignee: Daikin Industries Ltd.Inventors: Takashi Tohzuka, Ikuo Yamamoto, Yoshihiko Misugi
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Patent number: 4985590Abstract: Disclosed are novel optically active benzene derivatives represented by the formula (I): ##STR1## wherein R represents an alkyl or alkoxyalkyl group having 1 to 20 carbon atoms, which group may contain a halogen; Z represents a hydrogen atom or a halogen atom; l and n each represents a number of 0 or 1; and * indicates asymmetric carbon atom, anda process for preparing the above optically active benzene derivative which comprises debenzylating an optically active benzyl derivative represented by the formula (II): ##STR2## wherein, R, Z, l, n and * have the same meanings as defined above, and A represents a hydrogen atom, a lower alkyl group, a lower alkoxyl group or a halogen atom.Type: GrantFiled: April 18, 1988Date of Patent: January 15, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Masayoshi Minai, Takayuki Higashi
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Patent number: 4973748Abstract: A process for the preparation of perfluorinated carbonyl fluorides from hexafluoropropene oxide (HFPO) is described, in which HFPO is oligomerized in an aprotic polar solvent in the presence of a tertiary diamine in the absence or presence of at least one protonic compound. Preferably employed are tetraalkyl-substituted tertiary aliphatic diamine compounds. Protonic compounds which are possibly and preferably used are water, methanol, glycol, ammonia or diethylamine. The selectivity can be displaced in favor of shorter-chain oligomers, in particular of the dimer, by an increased content of these compounds.Type: GrantFiled: January 11, 1990Date of Patent: November 27, 1990Assignee: Hoechst AktiengesellschaftInventor: Heinz Strutz
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Patent number: 4973742Abstract: A halogen-containing polyether comprising repeating units 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.200and1.ltoreq.a+c+d+f,which may be prepared by ring-opening polymerizing 2,2,3,3-tetrafluorooxetane in the presence of a 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: April 14, 1989Date of Patent: November 27, 1990Assignee: Daikin Industries Ltd.Inventors: Yohnosuke Ohsaka, Takashi Tohzuka, Shoji Takaki
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Patent number: 4966989Abstract: A process for the production of 4-chloro-3-alkoxy-but-2E-enoic acid alkyl esters starting from 4-chloroacetoacetic acid chloride by reaction with a dialkyl sulfite. The produced intermediate products are used as structural elements for, i.a., pharmaceutical agents.Type: GrantFiled: June 8, 1989Date of Patent: October 30, 1990Assignee: Lonza Ltd.Inventor: Laurent Duc
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Patent number: 4940813Abstract: A process is described for the preparation of an optically active carboxylic acid or ester derivative thereof from a ketene and an optically active .alpha.-hydroxyester or an .alpha.-hydroxy amide.Type: GrantFiled: March 31, 1989Date of Patent: July 10, 1990Assignee: Merck & Co., Inc.Inventors: Edward G. Corley, Robert D. Larsen, Edward J. J. Grabowski, Paul Reider
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Patent number: 4933482Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a .beta.-keto acid derivative in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.Type: GrantFiled: June 9, 1988Date of Patent: June 12, 1990Assignee: Takasago International CorporationInventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
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Patent number: 4916252Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a 1,3-diketone in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.Type: GrantFiled: June 16, 1988Date of Patent: April 10, 1990Assignee: Takasago International CorporationInventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
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Patent number: 4912252Abstract: A synthetic lubricant comprising a compound represented by the following general formula (I): ##STR1## wherein Rf and Rf' represent a fluorine-containing polyoxyalkylene group, X and X' a polar group, Y of one or more selected from the group consisting of methylane, ethylene, propylene, oxygen, ketone, imino, sulfon and sulfur or no atom or group, and n an integer of 0 to 5, and a magnetic recording medium coated with this lubricant.Type: GrantFiled: December 22, 1987Date of Patent: March 27, 1990Assignees: Hitachi Metals, Ltd., Maruwa Bussan K.K.Inventors: Takateru Dekura, Juro Endo
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Patent number: 4895979Abstract: A process for preparing carnitine which comprises asymmetrically hydrogenating a .gamma.-halogeno-.beta.-keto ester represented by formula (I): ##STR1## wherein X represents a chlorine atom or a bromine atom; and R represents a lower alkyl group, in the presence of a ruthenium-optically active phosphine complex represented by formula (II), (III) or (IV):Ru.sub.2 Cl.sub.4 (L).sub.2 (C.sub.2 H.sub.5).sub.3 N (II)Ru(OCOR.sup.2).sub.2 (L) (IV)RuX.sub.2 (L) (V)wherein L represents 2,2'-bis(di-p-R.sup.1 -phenylphosphino)- 1,1'-binaphthyl of formula (III): ##STR2## wherein R.sup.1 represents a hydrogen atom, a methyl group, or a t-butyl group;R.sup.2 represents a lower alkyl group or a trifluoromethyl group; and X is as defined above,as a catalyst at a temperature of from 70.degree. to 150.degree. C.Type: GrantFiled: February 21, 1989Date of Patent: January 23, 1990Assignee: Takasago International CorporationInventors: Ryoji Noyori, Masato Kitamura, Takeshi Ohkuma, Hidenori Kumobayashi
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Patent number: 4855481Abstract: An intermediate compound of the formula ##STR1## wherein Y is chloro or bromo: Pr is a protecting group selected from benzoyl, acetyl, triphenylsilyl or t-butyldiphenylsilyl:R.sup.5 is C.sub.1-5 alkyl or benzyl; andR.sup.7 is C.sub.1-5 alkyl, benzyl, C.sub.2-5 alkoxyalkyl or C.sub.3-5 alkoxyalkoxyalkyl,useful for the preparation of certain HMG-CoA reductase inhibitors.Type: GrantFiled: April 4, 1988Date of Patent: August 8, 1989Assignee: Merck Frosst Canada, Inc.Inventors: Yvan Guindon, Christiane Yoakim, Howard E. Morton
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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: 4837357Abstract: 2,2-Disubstituted 3-chloropropionic esters I ##STR1## where R.sup.1 and R.sup.2 are each C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -oxaalkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -oxaalkenyl, aryl or C.sub.7 -C.sub.12 -aralkyl or R.sup.1 -C-R.sup.2 is 5-, 6- or 7-membered ring, R.sup.3 is C.sub.2 -C.sub.6 -oxaalkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -oxaalkenyl or C.sub.7 -C.sub.12 -aralkyl, are prepared by converting 2,2-disubstituted 3-hydroxypropanals II ##STR2## into the esterdiol III ##STR3## reacting this esterdiol III in the presence of a transesterification catalyst with an alcohol R.sup.3 OH to give the 3-hydroxyester IV ##STR4## reacting the hydroxyester IV with a stoichiometric or greater than stoichiometric amount of the thionyl chloride and thermally decomposing the product to give the chloropropionic ester I.Type: GrantFiled: October 21, 1987Date of Patent: June 6, 1989Assignee: BASF AktiengesellschaftInventors: Franz Merger, Peter Hettinger
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Patent number: 4760198Abstract: Perfluoropolyethers containing an approximate equal number of difluoromethylene and tetrafluoroethylene repeat units distributed either randomly or in alternating sequence along the polymer chain are disclosed. The polymers range in molecular weight from 500-200,000 amu; the lower molecular polymers being fluid and the intermediate and high molecular weight polymers being solid. The perfluorinated copolymers are synthesized by direct fluorination of corresponding methylene oxide/ethylene oxide copolymers.Type: GrantFiled: November 8, 1985Date of Patent: July 26, 1988Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Richard J. Lagow
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Patent number: 4749526Abstract: Fluoroaliphatic ether-containing carbonyl fluoride compounds are prepared by reacting a fluorinated carbonyl compound with hexafluoropropylene oxide in the presence of at least one catalyst selected from potassium iodide, potassium bromide, cesium iodide, cesium bromide, rubidium iodide, and rubidium bromide.Type: GrantFiled: September 12, 1986Date of Patent: June 7, 1988Assignee: Minnesota Mining and Manufacturing Co.Inventor: Richard M. Flynn
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Patent number: 4719052Abstract: 2,2,3-trifluoropropionyl fluoride is prepared by opening the ring of tetrafluorooxetane in the presence of a catalyst. Analogously, a novel 2,2-difluoropropionic acid derivative of the formula:XCH.sub.2 CF.sub.2 COY (I)wherein X is chlorine, bromine, iodine, a group of the formula:R.sub.1 O-- (II)orR.sub.2 COO-- (III)wherein R.sub.1 R.sub.2 are each an aliphaic or halogenated aliphatic hydrocarbon group having 1 to 8 carbon atoms or an aromatic hydrocarbon group having 6 to 8 carbon atoms optionally bearing at least one substituent, or a group of the formula:X'CH.sub.2 CF.sub.2 CF.sub.2 O-- (IV)wherein X' is fluorine, chlorine, bromine, iodine, the group of the formula: R.sub.1 O--or R.sub.2 COO--; and Y is fluorine or a group of the formula:--OR.sub.3 (V)wherein R.sub.Type: GrantFiled: December 20, 1984Date of Patent: January 12, 1988Assignee: Daikin Industries Ltd.Inventors: Yohnosuke Ohsaka, Takashi Tohzuka, Shoji Takaki, Yoshio Negishi, Satoru Kohno
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Patent number: 4709063Abstract: A method of preparing certain 2-halo-5-methylpyridines, useful as herbicide intermediates, is presented starting from acyclic pentenes. The pentene is difunctionalized, e.g., by making the epoxide, and is then reacted with a nitrogen source to close the ring. The nitrogen-containing 6-membered heterocycle may then be aromatized readily to produce the 2-halo-5-methylpyridine desired. Also part of the invention are novel acyclic and cyclic intermediates used in the process.Type: GrantFiled: August 8, 1986Date of Patent: November 24, 1987Assignee: ICI Americas Inc.Inventors: Richard V. Nelson, John F. Stephen
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Patent number: 4664852Abstract: A process for preparing L-carnitine (I) wherein(a) diketene (II) is reacted with chlorine, and the chlorination product thus obtained is submitted to amidation by the methylester of an optically-active aminoacid, having formula: ##STR1## wherein R=CH.sub.2 A.sub.r or A.sub.Type: GrantFiled: May 22, 1986Date of Patent: May 12, 1987Assignee: Sclavo S.p.A.Inventors: Paolo Casati, Claudio Fuganti
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Patent number: 4647413Abstract: Perfluoropolyether oligomers or block polymers, having a backbone with one or a plurality of perfluoropolyether segments each consisting essentially of (1) at least one perfluoroisopropyleneoxy unit, (2) a bis(perfluoromethyleneoxy-terminated) unit, and (3) a perfluoroethylidene unit terminating each segment, the backbone of the perfluoropolyether being terminated with COF and/or a functional or nonfunctional derivative thereof, said perfluoropolyethers being made by reacting a perfluoroaliphatic diacid fluoride with hexafluoropropylene epoxide to produce an acid fluoride-terminated perfluoropolyether adduct or oligomer which then can be photopolymerized to yield an acid fluoride-terminated perfluoropolyether block polymer. These oligomers and block polymers are useful as high temperature lubricants, hydraulic fluids, gaskets, adhesives and coatings as well as co-reactants wtih urethane in forming propellant binders.Type: GrantFiled: January 20, 1984Date of Patent: March 3, 1987Assignee: Minnesota Mining and Manufacturing CompanyInventor: Patricia M. Savu
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Patent number: 4647689Abstract: Alkyl trifluoroacetoacetates are prepared by acetylation of alkyl 3-alkoxy-3-hydroxy-4,4,4-trifluorobutanoates.Type: GrantFiled: July 30, 1982Date of Patent: March 3, 1987Assignee: Monsanto CompanyInventor: Edward Micinski
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Patent number: 4633013Abstract: Disclosed is a process for the preparation of .alpha.-haloacetoacetic esters by the reaction of an alkali metal alkoxide with a 5-halo-4H-1,3-dioxin-4-one compound, the desired product being obtained as an alkali metal salt which may be converted to the corresponding free ester by treating with acid.Type: GrantFiled: June 11, 1984Date of Patent: December 30, 1986Assignee: Eastman Kodak CompanyInventor: Robert J. Clemens
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Patent number: 4609673Abstract: The present invention provides carboxylic acid derivatives of the general formula: ##STR1## wherein R is a hydrogen atom, alkyl, a metal cation or an ammonium or alkylammonium ion, R.sub.1 is a hydrogen atom, a hydroxyl group or an alkyl, O-alkyl,O-benzyl or O-acyl radical, R.sub.2 is a hydrogen atom or an alkyl, aryl or aralkyl radical, n is 0, 1 or 2 and R.sub.Type: GrantFiled: December 18, 1984Date of Patent: September 2, 1986Assignee: Boehringer Mannheim GmbHInventors: Hermann Eggerer, Bernd Hagenbruch, Tran G. Nguyen, Karlheinz Stegmeier, Johannes Pill
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Patent number: 4582924Abstract: An .alpha.-fluoroalkyl carboxylic acid ester of the general formula ##STR1## wherein A is R.sup.1 R.sup.2 COR.sup.3 -- or R.sup.4 CO--, wherein R.sup.1 and R.sup.2 are independently hydrogen, alkyl, alkoxyl or phenyl, with or without the formation of a common ring therebetween, R.sup.3 is hydrogen or alkyl, R.sup.4 and R are independently alkyl, and R.sub.f is fluoroalkyl. The .alpha.-fluoroalkyl carboxylic acid ester is prepared by reacting a fluoroalkyl silyl ketene acetal of the formula ##STR2## wherein R' is alkyl and R.sub.f and R are the same as defined above, with the corresponding acetal, ketone or acyl halide.Type: GrantFiled: March 7, 1984Date of Patent: April 15, 1986Assignee: Daikin Kogyo Co., Ltd.Inventors: Nobuo Ishikawa, Takeshi Nakai
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Patent number: 4562282Abstract: Novel 4-methyl-3-formyl-pentanoic acid derivative of the formula ##STR1## wherein Hal is a halogen, R.sub.1 is alkyl of 1 to 12 carbon atoms and A and B are .dbd.O or A is halogen and B is --OR.sub.2 and R.sub.2 is alkyl of 1 to 12 carbon atoms, their preparation and their use as intermediates.Type: GrantFiled: June 17, 1985Date of Patent: December 31, 1985Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
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Patent number: 4531011Abstract: Alkyl perfluoro-.omega.-(2-iodoethoxy) compounds, vinyl ethers made therefrom, and a process for preparing the iodo-compounds. The vinyl ether monomers when copolymerized with halogenated 1-olefins are useful to form elastomers, rigid articles, or membranes and films having ion-exchange properties.Type: GrantFiled: March 4, 1983Date of Patent: July 23, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventor: Carl G. Krespan
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Patent number: 4495364Abstract: A fluorinated acid fluoride having an ester group which has the formula ##STR1## wherein A,p, q and R are defined below is produced by reacting a diacid fluoride having the formula ##STR2## wherein A represents a C.sub.1 -C.sub.10 bifunctional perfluoro group; p represents 0 or 1; q represents an integer of 1 to 8 with an alcohol having the formula ROH wherein R represents an organic group.Type: GrantFiled: February 14, 1980Date of Patent: January 22, 1985Assignee: Asahi Glass Company Ltd.Inventors: Masaaki Yamabe, Seiji Munekata
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Patent number: 4466926Abstract: A method for making alpha,omega-bis-fluorosulfatoperfluoroalkanes by reacting a perfluorinated alpha-olefin with peroxodisulfuryl difluoride in the liquid phase, and compounds of the formulaFSO.sub.2 -O-(CF.sub.2 -CF.sub.2).sub.n -O-SO.sub.2 F,useful as intermediates in making polymers.Type: GrantFiled: July 14, 1982Date of Patent: August 21, 1984Assignee: Hoechst AktiengesellschaftInventor: Hans Millauer
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Patent number: 4421928Abstract: Novel 4-methyl-3-formyl-pentanoic acid derivative of the formula ##STR1## wherein Hal is a halogen, R.sub.1 is alkyl of 1 to 12 carbon atoms and A and B are .dbd.0 or A is halogen and B is --OR.sub.2 and R.sub.2 is alkyl of 1 to 12 carbon atoms, their preparation and their use as intermediates.Type: GrantFiled: February 25, 1982Date of Patent: December 20, 1983Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
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Patent number: 4414280Abstract: Solutions and membranes formed therefrom are disclosed with solvents having completely halogenated, saturated, hydrocarbon backbones and solubility parameters within a particular range. Preferred solvent have at least one ether linkage. An exemplary solvent is ##STR1## wherein X is F, Cl, Br, and I; n is 0, 1, and 2; m is 1, 2, and 3; and Y is COOCH.sub.3 and SO.sub.2 F. The solutions include perfluorinated copolymers having high equivalent weight which have been prepared from tetrafluoroethylene and perfluorinated sulfonyl fluoride- or carboxyl-containing vinyl monomers.Type: GrantFiled: December 3, 1981Date of Patent: November 8, 1983Assignee: E. I. Du Pont de Nemours and CompanyInventors: Raimund H. Silva, Paul R. Resnick, Roger A. Smith
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Patent number: 4390720Abstract: Process for making alkyl-.omega.-fluoroformyl esters of the formula ##STR1## wherein R is CH.sub.3 or C.sub.2 H.sub.5 and n is 0 or an integer from 1 to 3, by reacting the methyl or ethyl ester of trifluoropyruvic acid with hexafluoropropene oxide in the presence of fluoride ion catalyst, in an aprotic liquid medium; and the ester wherein n=0.Type: GrantFiled: October 14, 1981Date of Patent: June 28, 1983Assignee: E. I. Du Pont de Nemours and CompanyInventor: Paul R. Resnick
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Patent number: 4348535Abstract: There are disclosed substituted lactones of the formula ##STR1## wherein A stands for --CH--CH.sub.2 X (X being Cl, Br or OH), --CHY--CHY-- (Y being Cl or Br), or ##STR2## and R.sup.1, R.sup.2 and R.sup.3 are the same or different radicals from the group of hydrogen and C.sub.1 to C.sub.10 alkyls, at least one of the radicals R.sup.1, R.sup.2 and R.sup.3 being such an alkyl radical, and process for making the same.Type: GrantFiled: December 19, 1980Date of Patent: September 7, 1982Assignee: Dynamit Nobel AGInventor: Hans-Georg Schmidt
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Patent number: 4348310Abstract: Solutions are disclosed with solvents having completely halogenated, saturated, hydrocarbon backbones and solubility parameters within a particular range. Preferred solvent have at least one ether linkage. An exemplary solvent is ##STR1## wherein X is F, Cl, Br, and I; n is 0, 1, and 2; m is 1, 2, and 3; and Y is COOCH.sub.3 and SO.sub.2 F. The solutions include perfluorinated copolymers having high equivalent weight which have been prepared from tetrafluoroethylene and perfluorinated sulfonyl fluoride- or carboxyl-containing vinyl monomers.Type: GrantFiled: August 8, 1980Date of Patent: September 7, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventors: Raimund H. Silva, Paul R. Resnick, Roger A. Smith