Halogen Containing Patents (Class 568/661)
  • Patent number: 5104987
    Abstract: This invention relates to a process for the alkoxylation of an active hydrogen-containing compound comprising contacting the active hydrogen-containing compound with an alkylene carbonate in the presence of a mixed metal oxide catalyst under conditions effective to alkoxylate the active hydrogen-containing compound.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: April 14, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Stephen W. King
  • Patent number: 5087764
    Abstract: 1,4-disubstituted 2,3-difluorobenzenes according to formula I are suitable as intermediates for the synthesis of liquid crystalline compounds.
    Type: Grant
    Filed: May 12, 1989
    Date of Patent: February 11, 1992
    Assignee: Merck Patent Gesellschaft mit beschrankter Hafung
    Inventors: Volker Reiffenrath, Joachim Krause
  • Patent number: 5079245
    Abstract: The compounds 2-trifluoromethyl-7-substituted-6,7,8,9-tetrahydro-[5H]-benzocycloheptenes are disclosed and disclosed to be useful in the treatment of metabolic illnesses such as diabetes, obesity, and their complications. A perferred compound is 2-trifluoromethyl-7-amino-6,7,8,9-tetrahydro-[5H-benzocycloheptane.
    Type: Grant
    Filed: July 5, 1989
    Date of Patent: January 7, 1992
    Assignee: Adir et Compagnie
    Inventors: Michel Wierzbicki, Pierre Hugon, Jacques Duhault, Francoise Lacour
  • Patent number: 5068462
    Abstract: A fluorine-substituted compound containing an ether bond and an intermediate thereof are described, which are represented by: ##STR1## wherein R represents a straight-chain alkyl group having 1 to 8 carbon atoms; n represents an integer of 2 to 7; m represents 1 or 2, X represents a hydrogen atom or a fluorine atom and ##STR2## represents a trans-(equatorial-equatorial)cyclohexane ring. A compound represented by formula (II): ##STR3## wherein R represents a straight-chain alkyl group having 1 to 8 carbon atoms; n represents an integer of 2 to 7; m represents 1 or 2, ##STR4## represents a trans-(equatorial-equatorial)cyclohexane ring.
    Type: Grant
    Filed: July 26, 1990
    Date of Patent: November 26, 1991
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Makoto Sasaki, Haruyoshi Takatsu, Kiyofumi Takeuchi
  • Patent number: 5030765
    Abstract: The present invention is concerned with novel tetrahydronaphthalene and indane derivatives of the formula ##STR1## useful as for combatting dermatoses as well as neoplasmas.
    Type: Grant
    Filed: October 16, 1990
    Date of Patent: July 9, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Loeliger, Peter Mohr, Ekkehard Weiss
  • Patent number: 5030764
    Abstract: Novel styryl-tetrahydronaphthalene and indane derivatives useful for treating neoplasms and dermatoses.
    Type: Grant
    Filed: October 15, 1990
    Date of Patent: July 9, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Loeliger, Peter Mohr, Ekkehard Weiss
  • Patent number: 4990703
    Abstract: Novel styryl-tetrahydromaphthalene and indane derivatives useful for treating neoplasms and dermatoses.
    Type: Grant
    Filed: May 11, 1989
    Date of Patent: February 5, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Loeliger, Peter Mohr, Ekkehard Weiss
  • Patent number: 4988826
    Abstract: The invention provides novel arylalkene compounds of formula I, a process for their preparation and their use as intermediates for insecticidal compounds, comprising, ##STR1## wherein W represents 1 to 4 substituents selected from halo, alkyl, alkoxy, haloalkyl, haloalkoxy and alkoxyalkyl, or W represents a bidentate alkylene or alkylenedioxy group linking adjacent carbon atoms, X represents fluoroalkyl, and Y is selected from chlorine, bromine and alkoxy; and a process for preparing said ethers. The compounds of formula I are prepared by reacting a ketone of formula: ##STR2## with a phosphonium salt of formula Hal.sup.- (Q).sub.3 P.sup.+ --CH.sub.2 --Y, where Hal.sup.- represents a halide ion and Q represents alkyl or aryl.
    Type: Grant
    Filed: September 25, 1989
    Date of Patent: January 29, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Robin A. E. Carr, Lyn Powell
  • Patent number: 4960884
    Abstract: Pesticidal mono-, di-, and tri-2-fluoroethyl ethers of the formula R.sup.1 R.sup.2.sub.m Ar(OCH.sub.2 CH.sub.2 F).sub.n, compositions thereof and their insecticidal, acaricidal and nematicidal uses are described and claimed.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: October 2, 1990
    Assignee: FMC Corporation
    Inventors: David M. Roush, Donald A. Shaw, Michael L. Jones, Jun H. Chang
  • Patent number: 4957986
    Abstract: Partially fluorinated polyesters are disclosed having increased biodegradability and water repellency. The incorporation of an ester group into the backbone of the partially fluorinated compound permits modification of the compound's physical properties.
    Type: Grant
    Filed: December 15, 1989
    Date of Patent: September 18, 1990
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Harry N. Cripps
  • 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: 4918215
    Abstract: Novel compounds of the formula ##STR1## and processes for their preparation are described. X represents bromine or iodine and R.sub.1, R.sub.2 and R.sub.3 have the meaning indicated in the patent claim. The compounds (I) are valuable intermediates for the preparation of fluorescent brighteners of the divinylstilbene type.
    Type: Grant
    Filed: October 3, 1984
    Date of Patent: April 17, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Dieter Reinehr, Alwyn Spencer
  • Patent number: 4918242
    Abstract: A process for producing the optically pure (+)- or (-)-isomer of a phenyl- or substituted-phenylalkanolamine compounds having pharmacologic activity without the need for resolution processes and novel intermediates useful in the process including optically pure haloalcohols are provided.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: April 17, 1990
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4902835
    Abstract: New chemical reactions of 1,1,2-trifluoro-1,3-butadiene provide simple access to a series of new fluorinated alkene derivatives. These derivatives provide a simple, general methodology for the stereocontrolled preparation of 2-fluoro-2-alkenoate esters and related monofluoroalkene derivatives which include fluoro analogs of known insecticides, pheromones or pharmaceuticals. A new method for the preparation of 1,1,2-trifluoro-1,3-butadiene is also provided.
    Type: Grant
    Filed: January 11, 1988
    Date of Patent: February 20, 1990
    Assignee: The University of Rochester
    Inventors: Andrew S. Kende, Noritada Matsuo
  • Patent number: 4895987
    Abstract: Ruthenium-cobalt- or cobalt-containing catalysts which have been promoted with phosphonites or phosphinites effectively catalyze the dealkoxyhydroxymethylation of aldehyde acetals to form glycol monoethers. Methylal, for example, may be reacted with syngas, i.e., CO and H.sub.2, in the presence of these phosphonite- or phosphinite-promoted cobalt or ruthenium- cobalt catalysts to form the monomethyl ether of ethylene glycol. In a like manner acetaldehyde may be converted to the corresponding propylene glycol monoether. The process may advantageously be carried out with high yields and selectivities in the presence of a polar or non-polar organic solvent in combination with the catalyst system of this invention.The invention is also directed to the phosphonite- or phosphonite-promoted cobalt and ruthenium-cobalt catalyst system per se.
    Type: Grant
    Filed: June 6, 1986
    Date of Patent: January 23, 1990
    Assignee: Sun Refining and Marketing Company
    Inventors: D. Michael Duggan, James E. Lyons, Harry K. Myers, Robert E. Ledley
  • 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: 4871470
    Abstract: Cyclohexane derivatives of formula I ##STR1## wherein R is an alkyl group which has 1-12 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by O, --CO--O-- or --OCO--,A.sup.1 and A.sup.2 each independently of one another are trans-1,4-cyclohexylene or unsubstituted or fluorine-substituted 1,4-phenylene, and one of the groups A.sup.1 and A.sup.2 can also be a single bond,X is --CN, halogen, OH, --COOR.sup.1, --OOCR.sup.1, --COR.sup.1, --OR.sup.1 or R.sup.1 andR.sup.1 is an alkyl group which has 1-12 C atoms and in which one or two CH.sub.2 groups can also be replaced by O, but excluding direct links between two O atoms,with the proviso that, in the case of X=CN, A.sup.2 is trans-1,4-cyclohexylene or fluorine-substituted, 1,4-phenylene, are suitable as components of liquid-crystalline phases.
    Type: Grant
    Filed: October 30, 1987
    Date of Patent: October 3, 1989
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Andreas Wachtler, Joachim Krause, Rudolf Eidenschink, Georg Weber
  • 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: 4853151
    Abstract: Dispirotetradecanes of the formula I ##STR1## wherein R.sup.1 and R.sup.2 are each independently of each other alkyl containing 1 to 12 carbon atoms wherein one or more non-adjacent CH.sub.2 groups may also be replaced by --O--, --CO--, --CO--O--, --O--CO--, --O--COO-- and/or --CH.dbd.CH-- (trans), one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, I, CN, NO.sub.2, NCS,A.sup.1 and A.sup.2 are each independently of each other trans-1,4-cyclohexylene wherein one or two non-adjacent CH.sub.2 groups may be replaced by --O-- and/or --S--, or 1,4-phenylene wherein one or more CH groups may also be replaced by N, with it also being possible optionally for A.sup.1 and A.sup.2 to be substituted laterally or axially by F, Cl, CN, CH.sub.3,Z.sup.1 and Z.sup.2 are each independently of each other --C--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 -- or a single bond,m and n are each 0, 1 or 2,(m+n) 0, 1 or 2,X.sup.1, X.sup.2, X.sup.3 and X.sup.
    Type: Grant
    Filed: August 11, 1987
    Date of Patent: August 1, 1989
    Assignee: Merck Patent Gesellschaft Mit Beschrankfter Haftung
    Inventors: Fritz Vogtle, Wolfgang Calaminus
  • Patent number: 4840971
    Abstract: An ether compound represented by the following general formula (I), its produciton method and an insecticidal and/or acaricidal composition containing it as an active ingredient: ##STR1## wherein R.sub.1 and R.sub.2, which may be identical or different, represent a hydrogen or halogen atom or a lower alkyl, lower haloalkyl, lower alkoxyl, lower haloalkoxyl, lower alkenyl or lower alkenyloxyl group, or represent, taken together, methylenedioxy, lower alkylene, ethyleneoxy or lower alkylethyleneoxy group; R.sub.3 represents a hydrogen or fluorine atom; R.sub.4 represents a hydrogen or halogen atom or a lower alkyl, lower haloalkyl, lower alkoxyl or lower haloalkoxyl group; m represents an integer of 1 or 2; Y represents an oxygen or sulfur atom or a group represented by the formula --CH.sub.2 -- or --NH--; and Z represents a nitrogen atom or a group represented by the formula --CH.dbd., and its starting materials.
    Type: Grant
    Filed: April 2, 1987
    Date of Patent: June 20, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazunori Tsushima, Noritada Matsuo, Yoo Tanabe, Toshihiko Yano, Masachika Hirano
  • Patent number: 4812483
    Abstract: A compound of formula:CXY.dbd.CH--CR.sup.1 R.sup.2 --CH.sub.2 OCH.sub.2 Rwherein X and Y are each selected from hydrogen and halogen, R.sup.1 and R.sup.2 are each lower alkyl of up to four carbon atoms, or together with the adjacent carbon atom form a cycloalkyl group of up to six carbon atoms, and R represents a phenoxy- or benzyl-substituted phenyl group which may optionally be substituted with fluorine. The compounds are useful for combating insect pests.
    Type: Grant
    Filed: December 9, 1986
    Date of Patent: March 14, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventor: Alan J. Whittle
  • Patent number: 4808762
    Abstract: Compounds of the formula ##STR1## in which Ar is substituted or unsubstituted phenyl, naphthyl, or thienyl; Z is oxygen, sulfur, or methylene; and Ar' is 2-methyl[1,1'-biphenyl]-3-yl, 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, or 6-phenoxy-2-pyridyl exhibit pyrethroid-like insecticidal and acaricidal activity and are relatively harmless to aquatic fauna.
    Type: Grant
    Filed: September 9, 1987
    Date of Patent: February 28, 1989
    Assignee: FMC Corporation
    Inventors: Gary A. Meier, Scott M. Sieburth, Thomas G. Cullen, John F. Engel
  • Patent number: 4792563
    Abstract: Insecticidally active compounds of the formula (I): ##STR1## wherein R.sup.4 represents a group selected from those groups represented by R.sup.5 in insecticidally active compounds of formula: ##STR2## R.sup.3 is selected from fluoromethyl and difluoromethyl, and either (a) R.sup.1 and R.sup.2 represent alkyl of one, two, three or four carbon atoms, or (b) R.sup.1 and R.sup.2 taken together with the adjacent carbon atom form a cycloalkyl ring of four, five or six carbon atoms.
    Type: Grant
    Filed: October 6, 1987
    Date of Patent: December 20, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventor: Alan J. Whittle
  • Patent number: 4786654
    Abstract: There are disclosed novel unsubstituted or substituted phenoxyfluorobenzyltetramethylcyclopropylmethyl ethers of formula ##STR1## wherein Y is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkyl which is substituted by 1 to 9 halogen atoms, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkoxy which is substituted by 1 to 9 halogen atoms, C.sub.1 -C.sub.4 alkylthio or C.sub.1 -C.sub.4 alkylthio which is substituted by 1 to 9 halogen atoms, or is C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkynyl and their benzyl ether intermediates of formula IV ##STR2## wherein X is halogen or p-tosyl. Also disclosed is a process for the preparation of these compounds and compositions containing them for use in pest control, especially for controlling insects that attack plants and animals, in particular their larval stages. The novel compounds are particularly effective against plant-destructive insects in rice crops.
    Type: Grant
    Filed: May 26, 1987
    Date of Patent: November 22, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Laurenz Gsell, Peter Ackermann
  • Patent number: 4742077
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 represents a group of formula ##STR2## whereby R.sub.4 and R.sub.5 are the same or different and represent hydrogen, halogen, lower alkyl, lower alkoxy or trifluoromethyl and X represents oxygen, sulfur, imino, lower alkylimino, --(CH.sub.2)--, --(S.CH.sub.2)-- or --(O.CH.sub.2)--,R.sub.2 represents hydrogen or lower alkyl,R.sub.3 represents a group of formula ##STR3## whereby R.sub.6, R.sub.7 and R.sub.8 are the same or different and represent hydrogen or alkyl or R.sub.6 together with R.sub.7 or R.sub.7 together with R.sub.8 represent --(CH.sub.2).sub.m -- wherein m is 3 to 6,R.sub.9 represents alkyl, alkenyl, trialkylsilyl or alkyl substituted by hydroxy, lower alkoxy, lower halogenalkyl or aryl andn stands for 1, 2 or 3,which possess pharmaceutical in particular antimycotic activity as well as activity against phytopathogenic fungi.
    Type: Grant
    Filed: September 8, 1986
    Date of Patent: May 3, 1988
    Assignee: Sandoz Ltd.
    Inventor: Anton Stutz
  • 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: 4707295
    Abstract: Bicyclooctane derivatives of the formula IR.sup.1 --A.sup.1 --A.sup.2 --R.sup.2 IwhereinR.sup.1 and R.sup.2 independently of one another are each an alkyl group which has 1-12 C atoms and in which it is also possible for one or two non-adjacent CH.sub.2 groups to be replaced by O atoms and/or CO groups and/or --O13 CO groups and/or --CO--O groups and/or --CH.dbd.CH-- groups, one of the radicals R.sup.1 and R.sup.2 being also --A.sup.3 --R.sup.3,A.sup.1 is a 1,4-cyclohexylene group which is unsubstituted or substituted in the 1-position and/or 2-position and/or 3-position and/or 4-position by alkyl which has in each case 1-5 C atoms and is unsubstituted or substituted or fluorinated, and in which it is also possible for one or two non-adjacent CH.sub.2 groups to be replaced by one or two different groupings from the group --O--, --CO--, --CH.dbd.CH--, --S--, --SO-- or --SO.sub.2 --, or is substituted by F, Cl, Br, CN and/or CHO,A.sup.2 is a 1,4-bicyclo[2.2.2] octylene group,--A.sup.3 --R.sup.3 is --Cy--R.sup.
    Type: Grant
    Filed: March 24, 1986
    Date of Patent: November 17, 1987
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Ludwig Pohl, Bernhard Scheuble, Andreas Wachtler, Reinhard Hittich, Peter Fuss
  • Patent number: 4695131
    Abstract: A fluorinated compound having a formula: ##STR1## R.sub.1 is hydrogen or alkyl having up to 12 carbon atoms; R.sub.2 is selected from hydrogen, alkyl having up to 12 carbon atoms, alkoxy having up to 12 carbon atoms, ##STR2## wherein R.sub.3 is hydrogen or alkyl having up to 12 carbon atoms, and wherein R.sub.4 is hydrogen, alkyl having up to 12 carbon atoms or alkoxy having up to 12 carbon atoms; ##STR3## represents a cyclohexane ring which is in the trans configuration if 1, 4-disubstituted; ##STR4## represents a benzene ring; each of X, Y and Z independently represents hydrogen or fluorine in one or more of the lateral benzene ring positions, provided that at least one of X, Y and Z is present representing fluorine;n=0 or 1 provided that when n=0 ##STR5## and R.sub.1 is alkyl; with the proviso that in Formula I when n is 1 and ##STR6## where R.sub.1 is n-alkyl and R.sub.2 is n-alkyl or n-alkoxy the total number of carbon plus oxygen atoms in the two groups R.sub.1 and R.sub.2 is less than 10.
    Type: Grant
    Filed: January 25, 1984
    Date of Patent: September 22, 1987
    Inventors: Peter H. Balkwill, David I. Bishop, Andrew D. Pearson, Ian C. Sage, George W. Gray, David Lacey, Kenneth J. Toyne, Damien G. McDonnell
  • Patent number: 4686289
    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: February 25, 1986
    Date of Patent: August 11, 1987
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Tuong Huynh-Ba, Maged A. Osman
  • Patent number: 4606845
    Abstract: New bicyclohexylethanes of formula IR.sup.1 --Cy--Cy--CH.sub.2 CH.sub.2 --A--(Cy).sub.n --R.sup.2 (I)wherein R.sup.1 is alkyl; R.sup.2 is alkyl, in which one or two non-adjacent CH.sub.2 groups can be replaced by O atoms, or is F, Cl, Br, CN, --COOalkyl or --O--CO-alkyl; or one of the radicals R.sup.1 and R.sup.2 can also be H; A is Cy, or 1,4-phenylene which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH.sub.3 groups or by a CN group; Cy is 1,4-cyclohexylene and n is 0 or 1; the alkyl groups in each case containing 1-10 C atoms, with the proviso that n is 1 if A is Cy and R.sup.2 is CN,can be used as constituents of dielectrics for electrooptical display elements.
    Type: Grant
    Filed: May 14, 1984
    Date of Patent: August 19, 1986
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Michael Romer, Rudolf Eidenschink, Joachim Krause, Bernhard Scheuble, Georg Weber
  • Patent number: 4575516
    Abstract: Substituted cyclopropylmethyl(ene) ethers of the formula ##STR1## in which X.sup.1 and X.sup.2 are identical or different and represent halogen,R.sup.1 represents hydrogen or alkyl,R.sup.2 and R.sup.3 are identical or different and represent hydrogen, alkyl, optionally substituted aryl, halogenoalkyl, hetero-alkyl, alkoxyalkyl, alkylthioalkyl, optionally substituted alkenoxyalkyl, optionally substituted alkinoxyalkyl or (di)alkylaminoalkyl,R.sup.4 represents hydrogen or alkyl,R.sup.5 and R.sup.6 are identical or different and represent hydrogen or optionally substituted radicals from the series comprising alkyl, aryl and aralkyl andR represents a trihalogenoalkenyl, alkinyl or iodoalkinyl radical,exhibit some arthropodicidal activity and synergize other known arthropodicides.
    Type: Grant
    Filed: February 1, 1984
    Date of Patent: March 11, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd-Wieland Kruger, Uwe Priesnitz, Gerhard Jager, Wolfgang Behrenz
  • Patent number: 4575517
    Abstract: Cyclopropylmethyl(ene) ethers have an outstanding action in microbicidal agents for preserving industrial materials from damage or destruction by microorganisms.
    Type: Grant
    Filed: February 16, 1984
    Date of Patent: March 11, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd-Wieland Kruger, Uwe Priesnitz, Gerhard Jager, Wilfried Paulus, Hermann Genth
  • Patent number: 4528406
    Abstract: Production of bis(alpha-alkylbenzyl)ethers or substituted derivatives thereof by reaction at elevated temperature of the corresponding alpha alkylbenzyl alcohols in the presence of a particular acidic clay catalyst, quenching of the catalyst and recovery of the desired ether by distillation directly from the reaction mixture containing the quenched catalyst, is disclosed. The alkyl methylbenzyl alcohol may be present as a component of an aromatic rich distilland product mixture derived from the ethyl benzene hydroperoxide epoxidation of an olefinically unsaturated compound.
    Type: Grant
    Filed: November 30, 1983
    Date of Patent: July 9, 1985
    Assignee: Atlantic Richfield Company
    Inventors: Mary T. Arnold, George R. Siciliano
  • Patent number: 4521635
    Abstract: Production of bis-(alpha-alkylbenzyl)ethers or substituted derivatives thereof by reaction at elevated temperature of the corresponding alpha alkylbenzyl alcohols in the presence of a mineral acid treated calcined alumina catalyst, quenching the catalyst with a basic compound and recovery of the desired ether by distillation following separation of the quenched catalyst, is disclosed. The alkyl methylbenzyl alcohol may be present as a component of an aromatic rich distill and product mixture derived from the ethyl benzene hydroperoxide epoxidation of an olefinically unsaturated compound.
    Type: Grant
    Filed: December 16, 1983
    Date of Patent: June 4, 1985
    Assignee: Atlantic Richfield Company
    Inventor: Frank Stevens
  • Patent number: 4521637
    Abstract: Production of bis-(alpha-alkylbenzyl)ethers or substituted derivatives thereof by reaction at elevated temperature of the corresponding alpha alkylbenzyl alcohols in the presence of an aryl sulfonic acid treated calcined alumina catalyst, quenching the catalyst with a basic compound and recovery of the desired ether by distillation following separation of the quenched catalyst, is disclosed. The alkyl methylbenzyl alcohol may be present as a component of an aromatic rich distilled product mixture derived from the ethyl benzene hydroperoxide epoxidation of an olefinically unsaturated compound.
    Type: Grant
    Filed: December 16, 1983
    Date of Patent: June 4, 1985
    Assignee: Atlantic Richfield Company
    Inventor: Frank Stevens
  • Patent number: 4431845
    Abstract: A method for the preparation of hydroxyl-terminated poly(haloalkylene ethers) is disclosed wherein a catalyst system comprising a fluorinated acid and a polyvalent tin compound is utilized.
    Type: Grant
    Filed: March 5, 1982
    Date of Patent: February 14, 1984
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Chung I. Young, Loren L. Barber, Jr.
  • Patent number: 4419264
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 are identical or different and each is alkyl or alkoxy each of up to 8 C atoms, and one or two of the substituents X are fluorine and the others are hydrogen are valuable liquid crystalline materials.
    Type: Grant
    Filed: April 30, 1982
    Date of Patent: December 6, 1983
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Rudolf Eidenschink, Michael Romer, Ludwig Pohl
  • Patent number: 4397864
    Abstract: The present invention relates to 2-arylpropyl ether or thioether derivatives represented by the following general formula [I]: ##STR1## wherein Ar stands for an aryl group, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula [II]: ##STR2## or the following general formula [III]: ##STR3## wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R.sup.1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R.sup.1 may be the same or different, and also to processes for the preparation or these ethers of thioethers and a use of these ethers or thioethers.These compounds of the present invention have excellent insecticidal and acaricidal activities while the toxicity of these compounds are very low.
    Type: Grant
    Filed: April 14, 1981
    Date of Patent: August 9, 1983
    Assignee: Mitsuitoatsu Chemicals Inc.
    Inventors: Kiyoshi Nakatani, Satoshi Numata, Tsuneo Inoue, Kenji Kodaka, Tsutomu Ishii, Teruhiko Toyama, Hajime Tachibana, Takatoshi Udagawa, Masatoshi Gohbara
  • Patent number: 4385185
    Abstract: Compounds of the general formula I: ##STR1## wherein R.sub.1 and R.sub.2 are equal or different alkyl-, alkoxyalkyl-, or aryl groups, or together form a ring; R.sub.3 is an allyl or benzyl radical; and R.sub.4 and R.sub.5 represent hydrogen, alkyl, alkoxyalkyl, alkenyl or further compounds of the formula II: ##STR2## wherein R.sub.1, R.sub.2, R.sub.4 and R.sub.5 have the meaning indicated above and R.sub.6 stands for hydrogen or methyl or to compounds which are modified by the addition of hydrogen to at least one olefinic or carbonylic double bond of compounds of the general formula I or II. The invention also relates to a process for preparing the new compounds. The compounds of the general formula II are obtained by thermal treatment of a selection of compounds of formula I, for which R.sub.3 stands for the allyl or methallyl radical. The compounds according to the invention are used as fragrant and flavoring substances.
    Type: Grant
    Filed: March 20, 1981
    Date of Patent: May 24, 1983
    Assignee: Consortium fur Elektrochemische Industrie GmbH
    Inventors: Helmut Gebauer, Walter Hafner
  • Patent number: 4368135
    Abstract: Anisotropic compounds with negative or positive DCA and .DELTA.n.ltoreq.0.2 have the formula (1) ##STR1## in which R.sup.1 and R.sup.2 l are independently hydrogen, alkyl, alkoxy having 1 to 12 carbon atoms respectively, or one of R.sup.1 and R.sup.2 can represent cyclical fragment of formulae (1a) or (1b); ##STR2## the bridges Z.sup.1, Z.sup.2 and Z.sup.3 are identical or different and means covalent bonds or carboxyl or oxycarbonyl groups; R.sup.3 is hydrogen, alkyl or alkoxy group having 1 to 12 carbon atoms, respectively; X.sup.1 and X.sup.4 are independently hydrogen, halogen, nitrile or nitro, wherein at least one of X.sup.1 and X.sup.4 is not hydrogen when R.sup.2 represents a cyclical fragment of formula (1a) or (1b) and Z.sup.2 is a carboxyl group or Z.sup.3 is an oxycarbonyl group, respectively. Liquid crystal compositions are also disclosed.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: January 11, 1983
    Assignee: BBC, Brown, Boveri & Company, Ltd.
    Inventor: Maged A. Osman
  • Patent number: 4361494
    Abstract: New anisotropic compounds suitable for use in LC-display devices are disclosed and claimed. The new compounds are cyclohexyl cyclohexylmethyl ethers of formula (1): ##STR1## in which X and Y are respectively hydrogen, alkyl group with 1 to 12 C-atoms, alkoxy group with 1 to 12 C-atoms, monoalkylamino group with 1 to 12 C-atoms, nitrile group, nitro group, halogen, or cyclic radical of formula (1a) or (1b): ##STR2## in which R.sup.1 and R.sup.2 represent hydrogen alkyl group with 1 to 12 C-atoms, alkoxy group with 1 to 12 C-atoms, monoalkylamino group with 1 to 12 C-atoms, nitrile group, nitro group or halogen, and Z.sup.1 and Z.sup.2 represent simple covalent bonds or grounds of the formulas --COO--, --OOC--, --CH.sub.2 O-- or --OCH.sub.2, with the requirement that only one of the groups X, Y can be a cyclicradical or formula (1a) or (1b). Also disclosed and claimed are LC-mixtures containing these compounds and methods for their synthesis.
    Type: Grant
    Filed: December 17, 1980
    Date of Patent: November 30, 1982
    Assignee: BBC Brown, Boveri, & Company, Limited
    Inventors: Maged A. Osman, Laszlo Revesz
  • Patent number: 4360698
    Abstract: A process to form glycol ethers by reacting an organic compound (A) having at least one aliphatic hydroxyl group with an oxirane compound (B) under reaction conditions in the presence of a catalytic amount of a polymeric material that is substantially insoluble in the reaction mixture, said polymeric material having a plurality of pendant sulfonate moieties with divalent metal counterions. Preferential formation of the mono adduct of glycol ethers is noted.
    Type: Grant
    Filed: July 22, 1981
    Date of Patent: November 23, 1982
    Assignee: The Dow Chemical Company
    Inventor: James H. Sedon
  • Patent number: 4326087
    Type: Grant
    Filed: July 30, 1980
    Date of Patent: April 20, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel, Erich Klauke
  • Patent number: 4326055
    Abstract: This invention is directed to 5,6,7,8-tetrahydro-naphthyl or indanyl stilbene derivatives which are useful as tumor inhibiting agents, in the treatment of neoplasms, dermatological conditions and rheumatic illnesses.
    Type: Grant
    Filed: December 15, 1978
    Date of Patent: April 20, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Peter Loeliger
  • Patent number: 4263212
    Abstract: The present invention relates to a process for the preparation of aromatic or furyl substituted olefins, which comprises reacting an olefinic compound with an aromatic compound or furan compound in the presence of carbon monoxide by using a rhodium carbonyl complex as a catalyst to form a corresponding aromatic or furyl substituted olefin.
    Type: Grant
    Filed: February 14, 1980
    Date of Patent: April 21, 1981
    Assignee: Rikagaku Kenkyusho
    Inventors: Pangbu Hong, Hiroshi Yamazaki
  • Patent number: 4243682
    Abstract: 4-(6-Substituted naphthyl)butan-2-ols,-butan-2-ones,-pentan-2-ols and -pentan-2-ones bearing a fluoro group in the naphthyl ring, and pro-drugs thereof, are anti-inflammatory agents. A typical embodiment is 4-(4-fluoro-6-methoxy-2-naphthyl)-butan-2-one.
    Type: Grant
    Filed: October 23, 1978
    Date of Patent: January 6, 1981
    Assignee: Beecham Group Limited
    Inventors: Alexander C. Goudie, Laramie M. Gaster
  • Patent number: 4235820
    Abstract: This invention relates to a process for the preparation of 5H-dibenzo[a,d]cycloheptene compounds and derivatives having aminoalkyl substituents at the 5-position by reducing the corresponding 5-aminoalkyl-5-hydroxy compounds with an alkali metal borohydride in trifluoroacetic acid.
    Type: Grant
    Filed: August 10, 1976
    Date of Patent: November 25, 1980
    Assignee: Merck & Co., Inc.
    Inventor: Ben E. Evans
  • Patent number: 4193931
    Abstract: Novel 7-(substituted indanyl or naphthyl)-3-methyl-octa-2,4,6-triene derivatives useful as anti-tumor agents are disclosed.
    Type: Grant
    Filed: April 24, 1978
    Date of Patent: March 18, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Peter Loeliger
  • Patent number: 4172839
    Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.2 series.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: October 30, 1979
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner