Halogen In Acid Moiety Patents (Class 560/184)
  • Patent number: 5324852
    Abstract: 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: Grant
    Filed: November 16, 1992
    Date of Patent: June 28, 1994
    Assignee: Chisso Corporation
    Inventors: Naoyuki Yoshida, Kazutoshi Miyazawa
  • Patent number: 5318769
    Abstract: 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: Grant
    Filed: March 31, 1993
    Date of Patent: June 7, 1994
    Assignee: Sterling Winthrop Inc.
    Inventors: Edward R. Bacon, Sol J. Daum, Kimberly G. Estep, Kurt A. Josef, Brent D. Douty, Carl R. Illig
  • Patent number: 5279764
    Abstract: 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: Grant
    Filed: November 23, 1992
    Date of Patent: January 18, 1994
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Volker Reiffenrath, Joachim Krause, Georg Weber, Ulrich Finkenzeller, Andreas Wachtler, Thomas Geelhaar, David Coates, Ian C. Sage, Simon Greenfield
  • Patent number: 5274179
    Abstract: 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: Grant
    Filed: April 6, 1993
    Date of Patent: December 28, 1993
    Assignee: AlliedSignal Inc.
    Inventor: Chengjiu Wu
  • Patent number: 5274180
    Abstract: 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: Grant
    Filed: October 22, 1992
    Date of Patent: December 28, 1993
    Assignee: British Petroleum Company plc
    Inventor: David Masheder
  • Patent number: 5264151
    Abstract: 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: Grant
    Filed: March 20, 1992
    Date of Patent: November 23, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takayuki Higashi, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Takeshi Tani, Chizu Kawakami, Koichi Fujisawa, Kiyoshi Imamura
  • Patent number: 5258547
    Abstract: 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: Grant
    Filed: January 9, 1992
    Date of Patent: November 2, 1993
    Assignee: Imperial Chemical Industries plc
    Inventor: Gary N. Sheldrake
  • Patent number: 5235094
    Abstract: 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: Grant
    Filed: December 11, 1991
    Date of Patent: August 10, 1993
    Assignee: The Dow Chemical Company
    Inventors: Kevin P. Darst, Marius W. Sorenson
  • Patent number: 5227516
    Abstract: 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: Grant
    Filed: December 18, 1991
    Date of Patent: July 13, 1993
    Assignee: Daikin Industries Ltd.
    Inventors: Takashi Tohzuka, Sueyoshi Ishikawa, Ikuo Yamamoto
  • Patent number: 5196543
    Abstract: 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: Grant
    Filed: July 19, 1991
    Date of Patent: March 23, 1993
    Assignee: Delalande S.A.
    Inventors: Francois X. Jarreau, Vincenzo Rovei, Jean-Jacques Koenig, Alain R. Schoffs
  • Patent number: 5153322
    Abstract: 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: Grant
    Filed: October 10, 1989
    Date of Patent: October 6, 1992
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Richard M. Flynn
  • Patent number: 5118836
    Abstract: 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: Grant
    Filed: November 8, 1990
    Date of Patent: June 2, 1992
    Assignee: Showa Shell Sekiyu Kabushiki Kaisha
    Inventors: Kaichi Tanida, Yoshiichi Suzuki
  • Patent number: 5113008
    Abstract: 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: Grant
    Filed: January 22, 1991
    Date of Patent: May 12, 1992
    Assignee: Monsanto Company
    Inventor: Mark J. Pozzo
  • Patent number: 5102911
    Abstract: HMG-CoA reductase inhibitors of formulae (I) and (II) are disclosed.
    Type: Grant
    Filed: July 6, 1990
    Date of Patent: April 7, 1992
    Assignee: Merck & Co, Inc.
    Inventors: Ta J. Lee, Wilbur J. Holtz
  • Patent number: 5099042
    Abstract: Polymers are produced from 4 and 5 member cyclic ethers, which polymers have hydroxyl functionalities of 4.
    Type: Grant
    Filed: March 14, 1989
    Date of Patent: March 24, 1992
    Assignee: Thiokol Corporation
    Inventors: Robert B. Wardle, Jerald C. Hinshaw
  • Patent number: 5051530
    Abstract: 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: Grant
    Filed: January 16, 1990
    Date of Patent: September 24, 1991
    Assignee: Korea Institute of Science and Technology
    Inventors: MoonHo Chang, Han-Young Kang, HunYeong Koh, YongSeo Cho, SangChul Shim
  • Patent number: 5023362
    Abstract: 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: Grant
    Filed: June 19, 1987
    Date of Patent: June 11, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Carl G. Krespan
  • Patent number: 5021453
    Abstract: Compounds of formula (I) and (II): ##STR1## are HMG-CoA reductase inhibitors.
    Type: Grant
    Filed: June 6, 1990
    Date of Patent: June 4, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Henry Joshua, Kenneth E. Wilson, Michael S. Schwartz, Ta J. Lee, Gerald E. Stokker
  • Patent number: 5004554
    Abstract: 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: Grant
    Filed: July 24, 1990
    Date of Patent: April 2, 1991
    Assignee: Daikin Industries Ltd.
    Inventors: Takashi Tohzuka, Ikuo Yamamoto, Yoshihiko Misugi
  • Patent number: 4985590
    Abstract: 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: Grant
    Filed: April 18, 1988
    Date of Patent: January 15, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masayoshi Minai, Takayuki Higashi
  • Patent number: 4973748
    Abstract: 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: Grant
    Filed: January 11, 1990
    Date of Patent: November 27, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Heinz Strutz
  • Patent number: 4973742
    Abstract: 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: Grant
    Filed: April 14, 1989
    Date of Patent: November 27, 1990
    Assignee: Daikin Industries Ltd.
    Inventors: Yohnosuke Ohsaka, Takashi Tohzuka, Shoji Takaki
  • Patent number: 4966989
    Abstract: 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: Grant
    Filed: June 8, 1989
    Date of Patent: October 30, 1990
    Assignee: Lonza Ltd.
    Inventor: Laurent Duc
  • Patent number: 4940813
    Abstract: 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: Grant
    Filed: March 31, 1989
    Date of Patent: July 10, 1990
    Assignee: Merck & Co., Inc.
    Inventors: Edward G. Corley, Robert D. Larsen, Edward J. J. Grabowski, Paul Reider
  • Patent number: 4933482
    Abstract: 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: Grant
    Filed: June 9, 1988
    Date of Patent: June 12, 1990
    Assignee: Takasago International Corporation
    Inventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
  • Patent number: 4916252
    Abstract: 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: Grant
    Filed: June 16, 1988
    Date of Patent: April 10, 1990
    Assignee: Takasago International Corporation
    Inventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
  • Patent number: 4912252
    Abstract: 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: Grant
    Filed: December 22, 1987
    Date of Patent: March 27, 1990
    Assignees: Hitachi Metals, Ltd., Maruwa Bussan K.K.
    Inventors: Takateru Dekura, Juro Endo
  • Patent number: 4895979
    Abstract: 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: Grant
    Filed: February 21, 1989
    Date of Patent: January 23, 1990
    Assignee: Takasago International Corporation
    Inventors: Ryoji Noyori, Masato Kitamura, Takeshi Ohkuma, Hidenori Kumobayashi
  • Patent number: 4855481
    Abstract: 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: Grant
    Filed: April 4, 1988
    Date of Patent: August 8, 1989
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Yvan Guindon, Christiane Yoakim, Howard E. Morton
  • Patent number: 4845268
    Abstract: 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: Grant
    Filed: December 9, 1986
    Date of Patent: July 4, 1989
    Assignee: Daikin Industries, Ltd.
    Inventors: Yohnosuke Ohsaka, Takashi Tohzuka, Shoji Takaki
  • Patent number: 4837357
    Abstract: 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: Grant
    Filed: October 21, 1987
    Date of Patent: June 6, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Peter Hettinger
  • Patent number: 4760198
    Abstract: 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: Grant
    Filed: November 8, 1985
    Date of Patent: July 26, 1988
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy J. Juhlke, Richard J. Lagow
  • Patent number: 4749526
    Abstract: 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: Grant
    Filed: September 12, 1986
    Date of Patent: June 7, 1988
    Assignee: Minnesota Mining and Manufacturing Co.
    Inventor: Richard M. Flynn
  • Patent number: 4719052
    Abstract: 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: Grant
    Filed: December 20, 1984
    Date of Patent: January 12, 1988
    Assignee: Daikin Industries Ltd.
    Inventors: Yohnosuke Ohsaka, Takashi Tohzuka, Shoji Takaki, Yoshio Negishi, Satoru Kohno
  • Patent number: 4709063
    Abstract: 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: Grant
    Filed: August 8, 1986
    Date of Patent: November 24, 1987
    Assignee: ICI Americas Inc.
    Inventors: Richard V. Nelson, John F. Stephen
  • Patent number: 4664852
    Abstract: 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: Grant
    Filed: May 22, 1986
    Date of Patent: May 12, 1987
    Assignee: Sclavo S.p.A.
    Inventors: Paolo Casati, Claudio Fuganti
  • Patent number: 4647413
    Abstract: 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: Grant
    Filed: January 20, 1984
    Date of Patent: March 3, 1987
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Patricia M. Savu
  • Patent number: 4647689
    Abstract: Alkyl trifluoroacetoacetates are prepared by acetylation of alkyl 3-alkoxy-3-hydroxy-4,4,4-trifluorobutanoates.
    Type: Grant
    Filed: July 30, 1982
    Date of Patent: March 3, 1987
    Assignee: Monsanto Company
    Inventor: Edward Micinski
  • Patent number: 4633013
    Abstract: 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: Grant
    Filed: June 11, 1984
    Date of Patent: December 30, 1986
    Assignee: Eastman Kodak Company
    Inventor: Robert J. Clemens
  • Patent number: 4609673
    Abstract: 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: Grant
    Filed: December 18, 1984
    Date of Patent: September 2, 1986
    Assignee: Boehringer Mannheim GmbH
    Inventors: Hermann Eggerer, Bernd Hagenbruch, Tran G. Nguyen, Karlheinz Stegmeier, Johannes Pill
  • Patent number: 4582924
    Abstract: 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: Grant
    Filed: March 7, 1984
    Date of Patent: April 15, 1986
    Assignee: Daikin Kogyo Co., Ltd.
    Inventors: Nobuo Ishikawa, Takeshi Nakai
  • Patent number: 4562282
    Abstract: 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: Grant
    Filed: June 17, 1985
    Date of Patent: December 31, 1985
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4531011
    Abstract: 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: Grant
    Filed: March 4, 1983
    Date of Patent: July 23, 1985
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Carl G. Krespan
  • Patent number: 4495364
    Abstract: 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: Grant
    Filed: February 14, 1980
    Date of Patent: January 22, 1985
    Assignee: Asahi Glass Company Ltd.
    Inventors: Masaaki Yamabe, Seiji Munekata
  • Patent number: 4466926
    Abstract: 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: Grant
    Filed: July 14, 1982
    Date of Patent: August 21, 1984
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Hans Millauer
  • Patent number: 4421928
    Abstract: 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: Grant
    Filed: February 25, 1982
    Date of Patent: December 20, 1983
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4414280
    Abstract: 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: Grant
    Filed: December 3, 1981
    Date of Patent: November 8, 1983
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Raimund H. Silva, Paul R. Resnick, Roger A. Smith
  • Patent number: 4390720
    Abstract: 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: Grant
    Filed: October 14, 1981
    Date of Patent: June 28, 1983
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Paul R. Resnick
  • Patent number: 4348535
    Abstract: 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: Grant
    Filed: December 19, 1980
    Date of Patent: September 7, 1982
    Assignee: Dynamit Nobel AG
    Inventor: Hans-Georg Schmidt
  • Patent number: 4348310
    Abstract: 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: Grant
    Filed: August 8, 1980
    Date of Patent: September 7, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Raimund H. Silva, Paul R. Resnick, Roger A. Smith