Halogen Containing Patents (Class 568/647)
  • Patent number: 5055235
    Abstract: A process is disclosed for preparing a mixture of brominated, non-condensed ring polyaromatics, which process features multiple bromination temperatures and multiple catalyst additions for brominating the precursor non-condensed ring polyaromatic. The mixture has an average bromine number of about 6 to about 8 bromine atoms per molecule, a low melting point range, and a low amount of light end impurities.
    Type: Grant
    Filed: December 12, 1990
    Date of Patent: October 8, 1991
    Assignee: Ethyl Corporation
    Inventors: David R. Brackenridge, William T. Murray
  • Patent number: 5047420
    Abstract: Novel 1,3-diaryl cyclopentanes of the following general formula were prepared. ##STR1## These compounds were found to have potent and specific PAF (Platelet Activating Factor) antagonistic activities and as such useful in the treatment or amelioration of various diseases or disorders mediate by the PAF, for example, hypotension, inflammation, nephritis, stroke and other cardiovascular disorders, asthma, allergic and skin diseases, peptic or stomach ulcer, shock, lung edema, psoriasis, adult respiratory distress syndrome, pain including dental pain, and aggregation of platelets.
    Type: Grant
    Filed: August 21, 1989
    Date of Patent: September 10, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Donald W. Graham, Tesfaye Biftu, John C. Chabala, Michael N. Chang, Yuan-Ching P. Chiang, Kathryn L. Thompson, Shu S. Yang
  • Patent number: 4983630
    Abstract: 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: Grant
    Filed: November 28, 1988
    Date of Patent: January 8, 1991
    Assignee: Schering Aktiengesellschaft
    Inventors: Peter Wegner, Hartmut Joppien, Gunter Homberger, Arnim Kohn
  • Patent number: 4956442
    Abstract: Poly(vinylbenzyl ethers) of polyphenols are prepared by reacting an alkali metal, alkaline earth metal, or ammonium salt of a polyphenol with a vinylbenzyl halide in a liquid reaction medium consisting essentially or a monohydric alcohol or glycol having less than 12 carbons, a polyglycol having a weight average molecular weight ranging from about 200 to about 4000, or glycerol.Halide ion content of poly(vinylbenzyl ethers) of polyphenols prepared by the method of this invention and other methods are reduced by dissolving the ether in a solvent that dissolves no more than about 1.0 weight percent of an alkali metal, alkaline earth metal, or ammonium halide; separating the ether solution from the halide salt; and then recovering the ether from the solution.
    Type: Grant
    Filed: September 23, 1987
    Date of Patent: September 11, 1990
    Assignee: The Dow Chemical Company
    Inventors: Ming-Biann Liu, James Godschalx, Ernest Ecker, Alfred Caldecourt
  • Patent number: 4956123
    Abstract: Fluorine-containing aromatic derivatives are produced by the reaction of di(haloacyl)peroxide represented by the general formula: ##STR1## (wherein X stands for a fluorine, chlorine, or hydrogen atom and n for an integer of the value of 1 to 10) with aromatic unsaturated monomers represented by the general formula: ##STR2## (wherein Y stands for hydrogen atom, methyl, ethyl, propyl, acetyl, propionyl, acetyloxy, propionyloxy, methoxy, ethoxy, propoxy, vinyl, isopropenyl, or nitro group, or a halogen atom, R.sup.1 for hydrogen atom, methyl, ethyl, propyl, or butyl group, R.sup.2 for hydrogen atom, methyl or phenyl group, and m for an integer of the value of 1 to 5).
    Type: Grant
    Filed: September 14, 1988
    Date of Patent: September 11, 1990
    Assignee: Nippon Oils & Fats Company, Ltd.
    Inventors: Hideo Sawada, Michio Kobayashi, Masato Yoshida
  • Patent number: 4918213
    Abstract: An optically active, generally mesomorphic compound represented by the following formula (I): ##STR1## wherein R.sub.1 denotes an alkyl group having 1-18 carbon atoms, R.sub.2 denotes an alkyl group having 1-12 carbon atoms; X denotes a single bond, --O--, ##STR2## Y denotes a single bond, ##STR3## --CH.sub.2 O-- or --OCH.sub.2 --; Z denotes --OCH.sub.2 --, ##STR4## respectively denotes ##STR5## C* denotes an asymmetric carbon atom; k, m and n are respectively 0, 1 or 2 with proviso that k+m+n amounts to 2 or 3; and p is 1 or 2.
    Type: Grant
    Filed: July 25, 1988
    Date of Patent: April 17, 1990
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiroyuki Nohira, Masanao Kamei, Hideki Kanazawa, Yoko Yamada, Yuko Etoh
  • Patent number: 4895672
    Abstract: A liquid crystal substance having a low viscosity and good compatibility thereof with existing liquid crystals at low temperatures in addition to a large optical anisotropy value and a high clearing point and a liquid crystal composition containing the substance are provided, which substance is a 4-(trans-4-alkylcyclohexylmethyloxy)-4'-substituted-tolan expressed by the formula ##STR1## wherein R.sup.1 is 1-10C alkyl and R.sup.2 is 1-10C alkyl or F or Cl.
    Type: Grant
    Filed: August 17, 1988
    Date of Patent: January 23, 1990
    Assignee: Chisso Corporation
    Inventors: Yasuyuki Goto, Toshiharu Suzuki
  • Patent number: 4877548
    Abstract: A liquid crystalline compound and a liquid crystal composition containing the compound usable for liquid crystal display devices are provided, which liquid crystalline compound is expressed by the formulaR.sup.1 --A.sup.1 --B.sup.1 --A.sup.2 --B.sup.2 --A.sup.3.sub.n (CH.sub.2).sub.m CH.dbd.CF.sub.2wherein R.sup.1 is H or 1-20C alkyl or alkenyl wherein one --CH.sub.2 --group or two --CH.sub.2 -- groups not adjacent to each other may be substituted by --O--; the position and number of the double bond may be optionally chosen; A.sup.1, A.sup.2 and A.sup.3 each are ##STR1## and the H of the ##STR2## may be substituted by F, Cl or methyl; B.sup.1 and B.sup.2 each are --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 -- or a single bond; n is 0 or 1; and m is 0-20.
    Type: Grant
    Filed: December 27, 1988
    Date of Patent: October 31, 1989
    Assignee: Chisso Corporation
    Inventors: Kisei Kitano, Makoto Ushioda, Manabu Uchida, Toshiharu Suzuki
  • Patent number: 4867903
    Abstract: 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: Grant
    Filed: March 6, 1987
    Date of Patent: September 19, 1989
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiroyuki Nohira, Masanao Kamei, Shinichi Nakamura, Kazuharu Katagiri
  • Patent number: 4855460
    Abstract: A process for the preparation of perfluoroalkylated ketones and/or perfluoroalkylated alcohols, comprising the step of contacting a perfluoroalkyl iodide or perfluoroalkyl bromide with an acid anhydride, in the presence of a metal chosen from zinc and cadmium.
    Type: Grant
    Filed: July 11, 1988
    Date of Patent: August 8, 1989
    Assignee: Rhone-Poulenc Chimie
    Inventors: Marc Tordeux, Claude Wakselman, Catherine Francese
  • Patent number: 4853414
    Abstract: Compounds of formula (I), useful as insecticides and knockdown agents: ##STR1## where Y is C.sub.1-6 alkoxy, Z is halo or C.sub.1-6 alkoxy; R is --(CH.sub.2).sub.p --(O).sub.m --R.sup.3 where m and p may be 0 or 1; R.sup.3 is C.sub.1-6 alkyl, phenyl or benzyl, or when m is 0, R.sup.3 is C.sub.1-6 alkenyl, haloalkenyl, alkynyl or haloalkynyl, and either (a) A and B are both C.sub.1-4 alkyl or (b) A is hydrogen and B is (R.sup.1)(R.sup.2)C.dbd.CH-- where R.sup.1 and R.sup.2 are selected from methyl, chloro, bromo, fluoro and trifluoromethyl.
    Type: Grant
    Filed: October 30, 1987
    Date of Patent: August 1, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael J. Robson, John Williams
  • Patent number: 4846998
    Abstract: Cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 Iin whichR.sup.1 and R.sup.2 are each an alkyl group having 1-10 C atoms, in which one or two non-adjacent CH.sub.2 groups can also be replaced by O atoms and/or --CO-- groups and/or --CO--O-- groups and/or --CH.dbd.CH-- groups, one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, A.sup.4 --A-- or --A--A.sup.4 --,A is a trans-1,4-cyclohexylene group which can be substituted in the 2-, 3-, 5- and/or 6-position one or more times by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group which each have 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups, and which may also be substituted in the 1- and/or 4-position,A.sup.2, A.sup.3 and A.sup.
    Type: Grant
    Filed: November 21, 1986
    Date of Patent: July 11, 1989
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Ludwig Pohl, Bernhard Scheuble, Reinhard Hittich, Rudolf Eidenschink, Hans A. Kurmeier, Andreas Wachtler
  • Patent number: 4791139
    Abstract: A compound of formula: ##STR1## wherein W represents one or more substituents selected from halo, alkyl, alkoxy, alkoxyalkyl, haloalkyl and haloalkoxy or W represents a bidentate group linking adjacent carbon atoms selected from alkylene and alkylenedioxy; Y is a group of formula ##STR2## wherein X is a group of formula --(CF.sub.2).sub.n R.sup.3, where R.sup.3 is selected from hydrogen, chloro and fluoro, and n is one or two, R.sup.1 is selected from hydrogen, chloro, fluoro and hydroxy and R.sup.2 is selected from methyl, cyano, ethynyl and hydrogen; Q is selected from carbon bearing a hydrogen atom and nitrogen; and Z represents one or more substituents selected from fluoro, benzyl, phenoxy, chlorophenoxy, fluorophenoxy and bromophenoxy, or any isomer thereof. Processes for preparing these compounds and intermediates for use therein, insecticidal compositions containing these compounds and the use thereof are also disclosed.
    Type: Grant
    Filed: February 25, 1987
    Date of Patent: December 13, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael J. Bushell, Robin A. E. Carr
  • Patent number: 4774316
    Abstract: The polyfunctional vinylbenzyl ethers of polyhydric halogenated phenolic compounds are prepared and can be copolymerized with polycyanate ester compounds to provide copolymers having dielectric constants below 3 and a V-O rating in a UL-94 test.
    Type: Grant
    Filed: August 15, 1986
    Date of Patent: September 27, 1988
    Assignee: The Dow Chemical Company
    Inventors: James P. Godschalx, Edmund P. Woo, Patricia A. Schrader, Peter D. Aldrich
  • Patent number: 4723005
    Abstract: New anisotropic compounds of the formula (1) are useful in liquid crystal mixtures for electrooptical displays; at least one of the end groups of the compounds (1) is an alkyl group which carries cyano or halogen in a terminal or non-terminal position. This offers advantages for longitudinal polarization and/or cross-polarization of the anisotropic compounds with the aid of the comparatively highly polarizing cyano or halogen substituents, in particular high clear points, low .DELTA..epsilon./.epsilon..perp. values and/or negative .DELTA..epsilon. values.
    Type: Grant
    Filed: September 10, 1984
    Date of Patent: February 2, 1988
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Tuong Huynh-Ba, Maged A. Osman
  • Patent number: 4710315
    Abstract: Anisotropic compounds of the formula (1) specified in claim 1 are suitable, owing to their low .DELTA..epsilon./.epsilon..perp. values for liquid crystal displays which have high information densities of for examples up to 10.sup.6 image dots and accordingly need to be highly multiplexible; compared with known compounds they offer improved application properties and are relatively simple to synthesize.
    Type: Grant
    Filed: December 16, 1985
    Date of Patent: December 1, 1987
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Hans P. Schad, Stephen M. Kelly
  • Patent number: 4659840
    Abstract: Provided is a method for preparing diaryl iodonium salts represented by the formula:[Ar.sub.1 --I.sup..sym. --Ar.sub.2 ]HSO.sub.4.sup..crclbar.wherein Ar.sub.1 and Ar.sub.2 respectively are an aryl group which may be substituted with an electron donor group and which may be the same or different which comprises subjecting a compound represented by the formula Ar.sub.1 --H wherein Ar.sub.1 is as defined above and a compound Ar.sub.2 --I wherein Ar.sub.2 is as defined above to a coupling reaction in a sulfuric acid solution containing an oxidizing agent and diluted with a diluting agent to a concentration of 85% by weight or less at a reaction temperature in the range from -20.degree. to +35.degree. C.
    Type: Grant
    Filed: March 8, 1984
    Date of Patent: April 21, 1987
    Assignee: Nippon Petrochemicals Co., Ltd.
    Inventors: Isoo Shimizu, Yasuo Matsumura, Yoshihisa Inomata
  • Patent number: 4637897
    Abstract: Nematic compounds with a negative DC antisotropy, characterized by the formula I ##STR1## in which m=1 or 2, r is zero or 1 and m+r=1 or 2, and R.sup.1 and R.sup.2 are identical or different and are selected from alkyl and alkoxy groups each having 1-12 carbon atoms in a straight or branched chain, which may be chiral, Z is a bridge member selected from a single bond and the groups of the formulae --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --O--CO-- or --CO--O--, one of the groups X and Y is selected from fluorine, chlorine, bromine and cyano and the other of the groups X and Y is selected from hydrogen, fluorine, chlorine, bromine and cyano, with the proviso that m=r=1 if X and Y are both cyano, are suitable as components for liquid crystal mixtures having an overall negative DC anisotropy, such as are required in particular for electro-optical displays of the type of guest/host displays or homotropic-nematic displays.
    Type: Grant
    Filed: August 6, 1984
    Date of Patent: January 20, 1987
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventor: Stephen M. Kelly
  • Patent number: 4629814
    Abstract: This process relates to the preparation of unsubstituted or substituted bis-bromoalkyl ethers by reacting unsubstituted or substituted 1,3-dioxolane or unsubstituted or substituted 1,3-dioxane with thionyl bromide. The bis-bromoalkyl ethers made by this process can be used in preparing biologically active compounds.
    Type: Grant
    Filed: August 27, 1985
    Date of Patent: December 16, 1986
    Assignee: Rohm and Haas Company
    Inventor: Michael P. James
  • Patent number: 4627933
    Abstract: 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: Grant
    Filed: July 7, 1983
    Date of Patent: December 9, 1986
    Assignees: 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 Ireland
    Inventors: Rudolf Eidenschink, Joachim Krause, Beatrice M. Andrews, George W. Gray, Neil Carr
  • Patent number: 4621901
    Abstract: Liquid crystalline mixtures containing compounds of the formula ##STR1## wherein n stands for the number 0 or 1; X.sup.1 and X.sup.2 denote single covalent bonds or one of the symbols X.sup.1 and X.sup.2 also denotes --COO--, --OOC-- or --CH.sub.2 CH.sub.2 --; the rings A.sup.1, A.sup.2, and A.sup.3 represent 1,4-phenylene, 2-fluoro-1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also represents a 2,5-disubstituted pyrimidine ring or a trans-2,5-disubstituted m-dioxane ring; R.sup.1 signifies 4-alkenyl or on a cyclohexyl ring also 2Z-alkenyl; and R.sup.2 denotes alkyl, alkoxy, --CN or --NCS,as well as the manufacture of these compounds and the use for electro-optical purposes are described.
    Type: Grant
    Filed: June 26, 1985
    Date of Patent: November 11, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Martin Petrzilka, Martin Schadt
  • Patent number: 4622163
    Abstract: 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: Grant
    Filed: September 10, 1984
    Date of Patent: November 11, 1986
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Tuong Huynh-Ba, Maged A. Osman
  • Patent number: 4618627
    Abstract: A catechol derivative represented by the formula ##STR1## The compounds of this invention are useful for the prophylaxis and treatment for various allergic diseases, ischemic heart diseases and inflammations caused by slow reacting substance of anaphylaxis (SRS-A), since the compounds inhibit very potently the formation and release of SRS-A.
    Type: Grant
    Filed: May 11, 1984
    Date of Patent: October 21, 1986
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Kiyoshi Murase, Toshiyasu Mase, Hideki Arima, Kenichi Tomioka
  • Patent number: 4558166
    Abstract: Process for the preparation of benzal chlorides from benzotrichlorides, according to which benzotrichlorides are reacted with thiols in the presence of metal salts at elevated temperatures.
    Type: Grant
    Filed: March 21, 1984
    Date of Patent: December 10, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd Baasner, Erich Klauke
  • Patent number: 4554360
    Abstract: Provided is a process for converting an aromatic compound to prepare an iodoarene, Ar--I, and an aryl compound which is a compound wherein an unsaturated compound is bonded directly to an aryl group, Ar, which process comprises reacting a diaryliodonium salt represented by general formula (I)[Ar--I.sup..sym. --Ar]X.sup..crclbar. (I)wherein Ar is an aryl group which may be substituted and two Ar's are identical and X.sup..crclbar. is a counter ion inert to the reaction with the unsaturated compound in a solvent in the presence of a transition metal catalyst and a base or a reducing metal, said reaction being carried out at a temperature not higher than 80.degree. C. and/or by using at least one of the base, the reducing metal and the unsaturated compound in an amount not more than 1.
    Type: Grant
    Filed: March 29, 1984
    Date of Patent: November 19, 1985
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Yasuo Yamazaki, Takehiko Suzuki, Isoo Shimizu, Yasuo Matsumura
  • Patent number: 4551264
    Abstract: New polyhalogenoaromatic compounds of Formula I ##STR1## wherein Y and Z are each independently alkyl, alkoxy or alkanoyl each of 1 to 12 C atoms, --COOR.sup.1, --O--CO--R.sup.1, CN, NO.sub.2, NH.sub.2 or OH;Q is one or two identical or different radicals selected from Ph, Cy, 1,4-bicyclo[2,2,2]octylene or 1,3-dioxane-2,5-diyl;X.sup.1 to X.sup.4 are each independently H, F, Cl or Br;R.sup.1 is alkyl of 1 to 4 C atoms, Ph--R.sup.2 or Cy--R.sup.2 ;R.sup.2 is alkyl or alkoxy each of 1-12 C atoms or CN;Ph is 1,4-phenylene; and Cy is 1,4-cyclohexylene,can be used as components of liquid-crystal dielectrics.
    Type: Grant
    Filed: March 14, 1983
    Date of Patent: November 5, 1985
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Rudolf Eidenschink, Michael Romer, Georg Weber
  • Patent number: 4545922
    Abstract: A Cyclohexylbiphenyl of the formula ##STR1## wherein R.sub.1 is alkyl of 1-12 C atoms;R.sub.6 is alkyl or alkoxy each of 1-12 C atoms, CN or fluorine; andR.sub.2, R.sub.3, R.sub.4 and R.sub.5 each is hydrogen or fluorine, with the proviso that at least one, but not more than two of R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are fluorine.
    Type: Grant
    Filed: September 21, 1983
    Date of Patent: October 8, 1985
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Rudolf Eidenschink, Ludwig Pohl
  • Patent number: 4538003
    Abstract: Process for the monoalkylation/monoarylation of dihaloaromatic compounds by treating the latter with selected magnesium or zinc organometallic reagents in the presence of a nickel/bidentate or tridentate phosphorus ligand. The products are intermediates to agricultural and pharmaceutical compounds.
    Type: Grant
    Filed: February 24, 1984
    Date of Patent: August 27, 1985
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Wilson Tam
  • Patent number: 4415470
    Abstract: A Cyclohexylbiphenyl of the formula ##STR1## wherein R.sub.1 is alkyl of 1-12 C atoms;R.sub.6 is alkyl or alkoxy each of 1-12 C atoms, CN or fluorine; andR.sub.2, R.sub.3, R.sub.4 and R.sub.5 each is hydrogen or fluorine, with the proviso that at least one, but not more than two of R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are fluorine.
    Type: Grant
    Filed: November 10, 1981
    Date of Patent: November 15, 1983
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Rudolf Eidenschink, Ludwig Pohl
  • Patent number: 4412082
    Abstract: A novel process for preparing 4-hydroxyphenylacetic acid which is useful as an intermediate for pharmaceutical is provided. A method for preparing 4-hydroxyphenylacetic acid comprising the steps of first reacting benzyl phenyl ether with formaldehyde and hydrogen chloride to form 4-benzyloxybenzyl chloride, second reacting the resultant 4-benzyloxybenzyl chloride with an alkali metal cyanide in at least one solvent selected from the group consisting of water and an organic solvent to form 4-benzyloxyphenylacetonitrile, and hydrolyzing the resultant 4-benzyloxyphenylacetonitrile in the presence of an acid catalyst.
    Type: Grant
    Filed: March 2, 1982
    Date of Patent: October 25, 1983
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Motoo Mutsukado, Shin Yamada
  • Patent number: 4400293
    Abstract: Cyclohexylphenyl derivatives of the formula ##STR1## wherein X is --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --O--, --CH.sub.2 --S--, --O--CH.sub.2 -- or --S--CH.sub.2 --; R.sub.1 is alkyl of up to 8 carbon atoms; R.sub.2 is alkyl or alkoxy each of up to 8 carbon atoms, fluorine, chlorine, bromine or cyano; and R.sub.3 and R.sub.4 are both hydrogen or one is hydrogen and the other is fluorine, chlorine, bromine or cyano, with the proviso that R.sub.3 and R.sub.4 are both hydrogen when X is --CH.sub.2 --CH.sub.2 -- or R.sub.2 is fluorine, chlorine, bromine or cyano, are valuable liquid crystalline compounds.
    Type: Grant
    Filed: October 29, 1981
    Date of Patent: August 23, 1983
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Michael Romer, Joachim Krause, Ludwig Pohl
  • Patent number: 4360700
    Abstract: Process for making 1-(3-benzyloxyphenyl)-1,1-dimethylheptane, a valuable intermediate for the preparation of analgesic agents, which comprises benzylation of 3-hydroxyacetophenone to produce 3-benzyloxyacetophenone which is converted to 1-(3-benzyloxyphenyl)-1-methylheptan-1-ol via Grignard reaction with n-hexylmagnesium bromide; chlorination of said heptanol by reaction with hydrogen chloride followed by methylation of the thus-produced 1-(3-benzyloxyphenyl)-1-chloro-1-methylheptane with trimethylaluminum.
    Type: Grant
    Filed: November 2, 1981
    Date of Patent: November 23, 1982
    Assignee: Pfizer Inc.
    Inventor: Lawrence S. Melvin, Jr
  • Patent number: 4357078
    Abstract: Novel liquid crystal compounds exhibiting a low dielectric anisotropy have a structural formula: ##STR1## where R.sub.1 is an alkyl group, R.sub.2 is a group containing an alkyl group R and is either an alkyl group R, an alkoxy group OR, an alkylcarbonyloxy group OCOR or an alkoxycarbonyloxy group OCOOR, R.sub.1 and R containing up to 18 carbon atoms, ##STR2## is a trans-1,4-disubstituted cyclohexane ring ##STR3## or a 1,4-disubstituted bicyclo(2,2,2)octane ring ##STR4## and Ar is a 1,4 disubstituted benzene ring ##STR5## a 3-fluoro-1,4 disubstituted benzene ring ##STR6## or a 2,6 disubstituted naphthalene ring ##STR7## These compounds may be used in liquid crystal mixture compositions for use in a number of known electro-optic effects.The compounds may be prepared by routes in which the individual steps involved are known.
    Type: Grant
    Filed: January 27, 1981
    Date of Patent: November 2, 1982
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Neil Carr, George W. Gray, Stephen M. Kelly
  • Patent number: 4346244
    Abstract: Chloroalkoxybenzenes are prepared by reacting a polychlorobenzene with at least one alkali metal hydroxide and an alcohol, ROH, in the presence of at least one tertiary amine sequestering agent having the formula:N--CHR.sub.1 --CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O).sub.n R.sub.5 ].sub.3.
    Type: Grant
    Filed: March 11, 1981
    Date of Patent: August 24, 1982
    Assignee: Rhone-Poulenc Industries
    Inventors: Gerard Soula, Louis Linguenheld
  • Patent number: 4336268
    Abstract: Cyclohexenes of the formula ##STR1## wherein R.sup.1 is hydroxy or lower alkoxy; n is 1 or 2; R.sup.2 is lower alkyl; and R.sup.3 is hydrogen, lower alkyl, lower alkenyl or lower cycloalkylmethyl, and their pharmaceutically acceptable acid addition salts are disclosed. The compounds of formula I have analgesic activity and are useful for the control of pains.
    Type: Grant
    Filed: January 27, 1981
    Date of Patent: June 22, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Hans Bruderer, Albert E. Fischli, Rudolf Pfister
  • Patent number: 4335055
    Abstract: Compounds of the formula I ##STR1## in which Z, Z.sub.1, R, m and p are as defined in patent claim 1, can be obtained in a simple and economical manner by a novel process wherein a halide of the formula II ##STR2## is reacted with a substituted or unsubstituted vinylbenzene or vinylnaphthalene derivative in the presence of a base and of certain palladium catalysts, such as palladium acetate. The compounds (I) or functional derivatives preparable therefrom are useful, for example, for the preparation of known dyes or fluorescent brighteners, or can be used directly as fluorescent brighteners or as scintillators.
    Type: Grant
    Filed: May 8, 1981
    Date of Patent: June 15, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Ulrich Blaser, Dieter Reinehr, Alwyn Spencer
  • Patent number: 4287125
    Abstract: Benzenoid ethers/thioethers are prepared by reacting an activated halobenzene with an anionic reactant, RA.sup.- M.sup.+, in the presence of at least one tertiary amine sequestering agent having formula:N--CHR.sub.1 --CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.
    Type: Grant
    Filed: June 20, 1980
    Date of Patent: September 1, 1981
    Assignee: Rhone-Poulenc Industries
    Inventor: Gerard Soula
  • Patent number: 4194054
    Abstract: A process for the preparation of a substituted fluorobenzene of the formula ##STR1## in which R is alkyl, alkoxy, halogen, amino, acylamido, carboxyl, benzyloxy, aryloxy, or benzyloxy or aryloxy carrying at least one alkyl, alkoxy, halogen or halogenoalkyl substituent,R.sup.1 each independently is alkyl or halogen, andn is an integer from 0 to 4, comprising reacting an N-aryl-N',N'-dialkyl-triazene of the formula ##STR2## in which Alkyl is alkyl with 1 to 4 carbon atoms, with about a 5 to 25-fold molar excess of anhydrous hydrofluoric acid at a temperature between about -20.degree. and +150.degree. C.
    Type: Grant
    Filed: November 7, 1977
    Date of Patent: March 18, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Forster, Hans Klusacek, Arthur Wenz
  • Patent number: 4180680
    Abstract: The title compounds are prepared in a process comprising contacting an alkali metal or alkaline earth metal salt of a tetra- or pentahalophenol with a vinylbenzyl chloride in a liquid, aqueous solvent containing from about 68 to about 90 weight percent of a C.sub.1 or C.sub.2 alkanol in a remaining amount of water. The contact of the aforementioned reactants occurs at a pH from about 7 to about 11 and at a temperature less than about 65.degree. C. As an example, sodium pentachlorophenoxide can be reacted with vinylbenzyl chloride by this process in an aqueous methanol solvent (with about 20 weight percent water) to yield about 90 percent pentachlorophenylvinylbenzyl ether, based on vinylbenzyl chloride.
    Type: Grant
    Filed: July 28, 1978
    Date of Patent: December 25, 1979
    Assignee: The Dow Chemical Company
    Inventor: Kent S. Dennis
  • Patent number: 4168388
    Abstract: Trifluoromethylphenols are prepared by hydrogenation of the corresponding trifluoromethylbenzylethers.
    Type: Grant
    Filed: March 23, 1978
    Date of Patent: September 18, 1979
    Assignee: Eli Lilly and Company
    Inventors: Edward R. Lavagnino, Bryan B. Molloy, Paul Pranc
  • Patent number: 4153719
    Abstract: Beta-diketones substituted by an aryl-aliphatic group in which the aliphatic chain is interrupted by a cyclic group, and useful as anti-viral agents, are prepared by interacting the appropriate aryl-aliphatic halide with an alkali metal salt of a beta-diketone.
    Type: Grant
    Filed: September 6, 1977
    Date of Patent: May 8, 1979
    Assignee: Sterling Drug Inc.
    Inventor: Guy D. Diana