Plural Benzene Rings Bonded Directly To Each Other Patents (Class 568/642)
-
Patent number: 6864397Abstract: The present invention provides a process for producing a difluoromethyl ether derivative simple and efficient process for producing the difluoromethyl ether derivative represented by Formula (1d?) or a difluoromethyl ether derivative represented by Formula (1c?): wherein all the variables are defined in the specification.Type: GrantFiled: June 18, 2003Date of Patent: March 8, 2005Assignees: Chisso Corporation, Chisso Petrochemical CorporationInventors: Tomoyuki Kondo, Kouki Sagou, Shuichi Matsui, Hiroyuki Takeuchi, Yasuhiro Kubo, Etsuo Nakagawa
-
Patent number: 6841502Abstract: New ligands and compositions with bridged bis-aromatic ligands are disclosed that catalyze the polymerization of monomers into polymers. These catalysts with metal centers have high performance characteristics, including higher comonomer incorporation into ethylene/olefin copolymers, where such olefins are for example, 1-octene, propylene or styrene. The catalysts also polymerize propylene into isotactic polypropylene.Type: GrantFiled: April 23, 2003Date of Patent: January 11, 2005Assignee: Symyx Technologies, Inc.Inventors: Thomas R. Boussie, Oliver Brümmer, Gary M. Diamond, Christopher Goh, Anne M. LaPointe, Margarete K. Leclerc, James A. W. Shoemaker
-
Patent number: 6784322Abstract: OLED materials are provided that have the general formula: R1—(Ari)n—R2 wherein the subscript n is an integer of from 5 to 15; the superscript i is an integer of from 1 to n and denotes the position downstream from R1; each Ari is a substituted or unsubstituted aryl group; R1 and R2 are each substituents that increase the solubility of the para-phenylene compound in nonpolar organic solvents relative to the solubility of the corresponding compound wherein R1 and R2 are hydrogen; with the proviso that the Ari groups are linked together in a 1,4-paraphenylene manner.Type: GrantFiled: April 10, 2001Date of Patent: August 31, 2004Assignee: Honeywell International Inc.Inventor: Gene Koch
-
Patent number: 6762330Abstract: Phosphine oxide and sulfoxide compounds were used with transition metals, preferably palladium and nickel, to produce biaryls, arylthiols, arylphosphine oxides and arylamines via cross-coupling reactions with aryl halides and arylboronic acids, aryl Grignard reagents, thiols, phosphine oxides or amines.Type: GrantFiled: July 6, 2001Date of Patent: July 13, 2004Assignee: E. I. du Pont de Nemours and CompanyInventor: George Y. Li
-
Patent number: 6605747Abstract: The present invention provides a difluoromethyl ether derivative which shows various suitable physical properties as a liquid crystal compound, a liquid crystal composition comprising the compound and a liquid crystal display element containing the composition, and also provides a simple and efficient process for producing the difluoromethyl ether derivative. According to the present invention, a process for producing a difluoromethyl ether derivative represented by Formula (1d): wherein the variables are defined in the specification, is characterized by using an &agr;&agr;-difluorocyclohexylidene derivative represented by Formula (1a): wherein R1, rings A1 and A2, Z1, Z2, k and l have the same meanings as defined in the specification, as a starting material.Type: GrantFiled: August 10, 2001Date of Patent: August 12, 2003Assignees: Chisso Corporation, Chisso Petrochemical CorporationInventors: Tomoyuki Kondo, Kouki Sagou, Shuichi Matsui, Hiroyuki Takeuchi, Yasuhiro Kubo, Etsuo Nakagawa
-
Patent number: 6586599Abstract: A process for conducting coupling reactions of aryl halides with unsaturated silanes is described. The processes use N-heterocyclic carbenes as ancillary ligands in these coupling reactions. A coupling of an aryl halide with an unsaturated silane can be carried out by mixing, in a liquid medium, at least one strong base; at least one aryl halide or aryl pseudohalide in which all substituents are other than silyl groups, wherein the aryl halide has, directly bonded to the aromatic ring(s), at least one chlorine atom, bromine atom, or iodine atom; at least one silane wherein the silicon atom is quaternary, wherein one group bound to the silicon atom is unsaturated at the alpha or beta position, and wherein each of the remaining groups bound to the silicon atom is a saturated hydrocarbyl or a saturated hydrocarbyloxy group; at least one nickel, palladium, or platinum compound, wherein the formal oxidation state of the metal is zero or two; and at least one N-heterocyclic carbene.Type: GrantFiled: April 20, 2000Date of Patent: July 1, 2003Assignee: University of New Orleans Research and Technology FoundationInventors: Steven P. Nolan, Hon Man Lee
-
Patent number: 6583307Abstract: A Pd(OAc)2/diazabutadiene system has been developed for the catalytic cross-coupling of aryl halides with arylboronic acids. A combination of the diazabutadiene DAB-Cy (1, N,N′-Dicyclohexyl-1,4-dizabutadiene) and Pd(OAc)2 was found to form an excellent catalyst for the Suzuki-Miyaura cross-coupling of various aryl bromides and activated aryl chlorides with arylboronic acids.Type: GrantFiled: March 7, 2002Date of Patent: June 24, 2003Assignee: University of New Orleans Research and Technology Foundation, Inc.Inventors: Steven P. Nolan, Gabriela Grasa
-
Publication number: 20020137974Abstract: Phosphine oxide and sulfoxide compounds were used with transition metals, preferably palladium and nickel, to produce biaryls, arylthiols, arylphosphine oxides and arylamines via cross-coupling reactions with aryl halides and arylboronic acids, aryl Grignard reagents, thiols, phosphine oxides or amines.Type: ApplicationFiled: July 6, 2001Publication date: September 26, 2002Inventor: George Y. Li
-
Patent number: 6444858Abstract: The present invention provides a method for alkoxylating organic compounds comprising contacting an organic compound adapted to be alkoxylated with an alkylene oxide in a reaction vessel under conditions effective to alkoxylate the organic compound. The alkylene oxide is maintained in vapor form during transport to said reaction vessel, during discharge into said reaction vessel, and during contacting of the organic compound with the alkylene oxide. The result is an alkoxylated product containing less flocculant.Type: GrantFiled: April 19, 1999Date of Patent: September 3, 2002Assignee: Baker Hughes IncorporatedInventor: Philip Leung
-
Patent number: 6417357Abstract: This invention relates to a novel, inventive process for the preparation of biphenyls or aromatic olefins by coupling reactions of the Suzuki coupling and Heck coupling type, using allylpalladium catalysts of the &mgr;-halo(triisopropylphosphine)(&eegr;3-allyl)palladium(II) type.Type: GrantFiled: September 14, 2000Date of Patent: July 9, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Michael Tinkl, Andreas Hafner
-
Patent number: 6291722Abstract: Phosphine oxide compounds were used with transition metals, preferably palladium and nickel, to produce biaryls and arylamines via cross-coupling reactions with aryl halides and arylboronic acids, aryl Grignard reagents or amines.Type: GrantFiled: June 26, 2000Date of Patent: September 18, 2001Assignee: E. I. du Pont de Nemours and CompanyInventor: George Yanwu Li
-
Patent number: 6278028Abstract: An electroclinic device having two spaced cell walls each bearing electrode structures and treated on at least one facing surface with an alignment layer, a layer of a smectic liquid crystal material enclosed between the cell walls, where the liquid crystal material contains one or more of the compounds described by formula I as defined in the specification.Type: GrantFiled: March 7, 2000Date of Patent: August 21, 2001Assignee: The Secretary of State for in Defence in Her Brittanic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Andrew John Slaney, Damien Gerard McDonnell, Amarjit Kaur Samra, Maurice Stanley, Victoria Minter, John William Goodby, Michael Hird, Simon John Cross, Chu Chuan Dong
-
Patent number: 6218564Abstract: A process for the preparation of a substituted aromatic compound in which a chloroaromatic compound and an alkyl-, alkenyl- or aryl-boronic acid ester or anhydride are coupled in the presence of palladium and a lipophilic aliphatic phosphine comprising at least one branched aliphatic group or a lipophilic aliphatic Dis(phosphine). Preferred phosphines include triisopropyl, triisobutyl and tricyclohexylphosphine.Type: GrantFiled: June 10, 1999Date of Patent: April 17, 2001Assignee: Zeneca LimitedInventor: Michael John Monteith
-
Patent number: 6124462Abstract: Phosphine oxide compounds were used with transition metals, preferably palladium, to produce biaryls and arylamines via cross-coupling reactions with aryl halides and arylboronic acids or amines.Type: GrantFiled: November 30, 1999Date of Patent: September 26, 2000Assignee: E. I. du Pont de Nemours and CompanyInventor: George Y. Li
-
Patent number: 6066766Abstract: 4-Chlorobiphenyls are prepared by reacting a haloaromatic with an aryl Grignard compound, where halogen is chlorine, bromine or iodine, in the presence of a palladium catalyst of the formula (IV) ##STR1##Type: GrantFiled: August 3, 1999Date of Patent: May 23, 2000Assignee: Clariant GmbHInventors: Steffen Haber, Stefan Scherer, Andreas Meudt, Antje Noerenberg
-
Patent number: 5969147Abstract: New pesticidal substituted biphenyloxazolines of the formula (I) in whichA, B, X, m and n have the meanings stated in the description, and new intermediates therefor.Type: GrantFiled: November 12, 1998Date of Patent: October 19, 1999Assignees: Bayer Aktiengesellschaft, Yashima Chemical Industry Co., LtdInventors: Reinhard Lantzsch, Albrecht Marhold, Wolfgang Kramer, Christoph Erdelen, Ulrike Wachendorff-Neumann, Andreas Turberg, Norbert Mencke
-
Patent number: 5827333Abstract: Substituted biphenyl polyalkyl ethers having the formula: ##STR1## wherein R.sub.1 is hydrogen or hydroxyl; R.sub.2 is hydroxyl, cyano, nitro, amino, aminomethyl, N-alkylamino or N-alkylaminomethyl wherein the alkyl group contains 1 to about 6 carbon atoms, N,N-dialkylamino or N,N-dialkylaminomethyl wherein each alkyl group independently contains 1 to about 6 carbon atoms, with the proviso that R.sub.1 and R.sub.2 are ortho relative to each other and meta or para relative to the adjoining phenyl substitutent; and R.sub.3 is a polyalkyl group having an average molecular weight in the range of about 450 to about 5,000.The subsitituted biphenyl polyalkyl ethers of the present invention are useful as fuel additives for the prevention and control of engine deposits.Type: GrantFiled: September 30, 1997Date of Patent: October 27, 1998Assignee: Chevron Chemical Company LLCInventor: Richard E. Cherpeck
-
Patent number: 5723621Abstract: A novel process for producing a biaryl compound represented by formula (III), which is useful as a medicine, an agricultural chemical and an electrooptical liquid-crystal display material:Ar--Ar' (III)(wherein Ar and Ar' each independently represents a substituted or unsubstituted aromatic group) which comprises the steps of (i) reacting a trialkoxysilyl-substituted aromatic compound represented by formula (I):Ar--Si(OR).sub.3 (I)(wherein Ar has the same meaning as defined above and R represents an alkyl group having from 1 to 5 carbon atoms) with a fluoride ion source in the presence of a solvent, and then (ii) adding thereto an aromatic compound represented by formula (II):X--Ar' (II)(wherein X represents an eliminating group and Ar' has the same meaning as defined above) and a catalyst comprising a transition metal of tenth group to conduct a further reaction.Type: GrantFiled: May 14, 1996Date of Patent: March 3, 1998Assignee: Chisso CorporationInventors: Koichi Shibata, Shuichi Matsui, Kazutoshi Miyazawa
-
Patent number: 5686608Abstract: A process for preparing polycyclic aromatic compounds by cross-coupling aromatic boron compounds with aromatic halogen compounds or perfluoroalkylsulfonates in the presence of metallic palladium as catalyst comprises adding to the reactiona) at least one water-soluble complexing ligand andb) sufficient water for the reaction mixture to form an aqueous phase.The reaction of the invention proceeds chemoselectively so that even electrophilic groups such as esters or nitriles do not have an adverse effect on the course of the reaction.The use according to the invention of a water-soluble complexing ligand in an aqueous phase enables polycyclic aromatic compounds to be prepared in very good yields and at the same time very high purity, in particular without contamination by the complexing ligands.Type: GrantFiled: April 24, 1995Date of Patent: November 11, 1997Assignee: Hoechst AktiengesellschaftInventors: Steffen Haber, Javier Manero
-
Patent number: 5679285Abstract: Vinylene compounds of the formula I ##STR1## in which R, A.sup.1, Z.sup.1, X, L.sup.1, L.sup.2 and m have the meaning given in claim 1 are suitable as components of liquid-crystalline media.Type: GrantFiled: February 15, 1996Date of Patent: October 21, 1997Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ekkehard Bartmann, Sabine Schoen, Kazuaki Tarumi
-
Patent number: 5599952Abstract: Methods of producing carboxylic acid ester derivatives of formulae (I) and (II), which are useful, for instance, as intermediates for producing an anti-hypercholesterolemic agent having an inhibitory effect on HMG-CoA Reductase: ##STR1## wherein R.sup.1 and R.sup.2 are independently a protective group for hydroxyl group, or R.sup.1 and R.sup.2 integrally constitute a protective group for hydroxyl groups; R.sup.3 is an alkyl group, or an aryl group; and R.sup.4 is a substituted aryl group, a substituted heterocyclic group, a substituted vinyl group, or a substituted cycloalkenyl group; and ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are respectively the same as defined in the above formula (I), are disclosed. In addition, intermediates for use in these methods of producing the carboxylic acid ester derivatives are disclosed.Type: GrantFiled: May 18, 1995Date of Patent: February 4, 1997Assignee: Fujirebio Inc.Inventors: Masakatsu Matsumoto, Nobuko Watanabe, Eiko Mori, Hisako Kobayashi, Hiroshi Ikawa
-
Patent number: 5550236Abstract: A process for preparing polycyclic aromatic compounds by cross-coupling aromatic boronic acids with aromatic halogen compounds or perfluoroalkylsulfonates in the presence of metallic palladium, if desired applied to a support material, as catalyst, wherein the coupling is carried out in the presence of a ligand and a base. The process of the invention allows the yield of polycyclic aromatic compounds to be significantly increased in comparison with processes not using a ligand and thus allows a yield optimum for the Pd(0)-catalyzed cross-coupling of aromatic boronic acids with aromatic halogen compounds to be achieved.Type: GrantFiled: April 24, 1995Date of Patent: August 27, 1996Assignee: Hoechst AktiengesellschaftInventors: Hubert Schlosser, Rainer Wingen, Javier Manero
-
Patent number: 5494605Abstract: The p-terphenyl derivatives of the formula shown below are useful in preparing practical ferroelectric liquid crystalline compositions. The derivatives exhibit excellent chemical stability and display the chiral smectic C or smectic C phase over a wide temperature range. ##STR1## wherein each of R.sub.1 and R.sub.2 is a straight or branched chain alkyl group having 1-18 carbon atoms; each of Y and Z is a single bond, O, COO or OCO; and any two of X.sub.1, X.sub.2, and X.sub.3 are fluorine atoms and the remainder is a hydrogen atom.Type: GrantFiled: November 24, 1993Date of Patent: February 27, 1996Assignee: Kanto Kagaku Kabushiki KaishaInventors: Makoto Kurihara, Hiromi Inoue, Atsushi Sugiura, Kenji Suzuki, Tsunenori Fujii
-
Patent number: 5399291Abstract: Fluorine-containing, chiral and achiral liquid crystal compounds comprise (a) an aliphatic fluorocarbon terminal portion comprising a perfluorinated or partially-fluorinated alkylene group and a terminal hydrocarbon alkyl group, the groups optionally containing at least one catenary ether oxygen atom; (b) an aliphatic hydrocarbon terminal portion; and (c) a central core connecting the terminal portions. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.Type: GrantFiled: September 30, 1993Date of Patent: March 21, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventors: Eugene P. Janulis, Gilbert C. Johnson, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
-
Patent number: 5397504Abstract: A new biphenyl compound which is chemically stable and possesses practically excellent properties as a component for preparing ferroelectric smetic liquid crystalline compositions as well as a new liquid crystalline composition containing this compound.Type: GrantFiled: January 10, 1994Date of Patent: March 14, 1995Assignee: Kanto Kagaku Kabushiki KaishaInventors: Kazuhiko Tsuchiya, Kenji Suzuki, Atsushi Sugiura, Tsunenori Fujii
-
Patent number: 5382380Abstract: New p-terphenyl derivatives useful as components for preparing practical ferroelectric liquid crystalline compositions and excellent in chemical stability, as well as liquid crystalline compositions containing at least one of the p-terphenyl derivatives.Type: GrantFiled: June 1, 1992Date of Patent: January 17, 1995Assignee: Kanto Kagaku Kabushiki KaishaInventors: Makoto Kurihara, Hiromi Inoue, Atsushi Sugiura, Kenji Suzuki, Tsunenori Fujii
-
Patent number: 5366656Abstract: Optically active compounds of general formulae ##STR1## wherein A is O or S, R.sub.1 is a hydrogen atom, an alkyl group having 1-22 carbon atoms, a hydroxy containing alkyl group, para-alkyl substituted phenyl, para-alkyl substituted biphenyl, hydroxyphenyl, hydroxybiphenyl or tosyl; R.sub.2 is an alkyl group having 2-8 carbon atoms; m is an integer of 0-5, n is 0 or 1, where when m=0, n is not 1; p is 0 or 1; q is 0 or 1; D and E are independently H or a halogen atom; R.sub.3 is a linear alkyl group having 1 to 22 carbon atoms; and * and ** are asymmetric centers.Type: GrantFiled: February 24, 1994Date of Patent: November 22, 1994Assignee: Industrial Technology Research InstituteInventors: Wen-Liang Tsai, Shu-Hui Yang
-
Patent number: 5328643Abstract: The invention relates to optically active compounds represented by the general formula I ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, Q.sub.1, Q.sub.2, Q.sub.3, and M are defined as in the specification, methods and intermediates for their preparation, liquid crystal compositions comprising at least one optically active compound of formula I and their use in electrooptical display, switching and modulation devices.Type: GrantFiled: February 26, 1992Date of Patent: July 12, 1994Assignees: Takeda Chemical Industries, Ltd., Hitachi, Ltd.Inventors: Yuka Sudo, Katsumi Kondo, Teruo Kitamura, Koichi Matsumura, Mitsuru Kawada, Yoshihiro Sugihara
-
Patent number: 5312975Abstract: A process for the preparation of 5-(2,4-difluorophenyl)-salicylic acid comprising the reaction of an organometallic derivative with a suitable substituted benzene in the presence of a transition-metal based catalyst is described.Type: GrantFiled: December 27, 1991Date of Patent: May 17, 1994Assignee: Zambon Group S.p.A.Inventors: Claudio Giordano, Laura Coppi, Francesco Minisci
-
Patent number: 5262082Abstract: Fluorine-containing liquid crystal compounds are provided. The compounds comprise a fluorocarbon terminal portion having at least one catenary ether oxygen and a hydrocarbon terminal portion, the terminal portion being connected by a central core, the compounds having smectic mesophases or having latent smectic mesophases.Type: GrantFiled: April 28, 1992Date of Patent: November 16, 1993Assignee: Minnesota Mining and Manufacturing CompanyInventors: Eugene P. Janulis, Gilbert C. Johnson, Patricia M. Savu, Terence D. Spawn
-
Patent number: 5238603Abstract: A liquid crystal compound having specific features suitable to use for a display mode utilizing ferroelectric liquid crystals, particularly a large spontaneous polarization value and a liquid crystal composition using the compound are provided, which compound is an optically active liquid crystalline compound of the formula ##STR1## wherein l and m each are 0 or 1; at least one of R.sup.1 and R.sup.2 is an optically active alkoxy group of the formula ##STR2## wherein R.sup.3 is 2 or 3C alkyl and R.sup.4 is 3-18C alkyl, but R.sup.3 .noteq.R.sup.4 and the other thereof is 1-20C alkyl, alkoxy or alkanoyloxy, halogen or cyano; and A is a specified two or three rings compound.Type: GrantFiled: April 7, 1992Date of Patent: August 24, 1993Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Naoyuki Yoshida, Masakazu Kaneoya
-
Patent number: 5204018Abstract: Compounds of the formula ##STR1## wherein n stands for the number 0 or 1; R.sup.1 denotes a group R.sup.3 or R.sup.3 --A.sup.3 --Z.sup.2 -- and R.sup.2 denotes a group R.sup.4 or R.sup.4 --A.sup.4 --Z.sup.3 --; ring A.sup.1 signifies unsubstituted or halogen-, cyano- and/or methyl-substituted 1,4-phenylene in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen; A.sup.3, A.sup.4 and ring A.sup.2 each independently represent unsubstituted or halogen-, cyano- and/or methyl-substituted 1,4-phenylene in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen or trans-1,4-cyclohexylene, trans-1,3-dioxane-2,5-diyl, 1-cyano-trans-1,4-cyclohexylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, tetralin-2,6-diyl or trans-decalin-2,6-diyl; Z.sup.1, Z.sup.2 and Z.sup.3 each independently signify a single covalent bond, --COO--, --OOC--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.tbd.C--, --(CH.sub.2).sub.3 O--, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 -- or the trans form of --CH.Type: GrantFiled: January 22, 1991Date of Patent: April 20, 1993Assignee: Hoffmann-La Roche Inc.Inventor: Stephen Kelly
-
Patent number: 5171470Abstract: A bifunctional optically active liquid crystal intermediate compound represented by the following Formula (I): X--Y--C.sub.* H(M)--CH.sub.2 --OH is disclosed, wherein X represents CH.sub.2 .dbd.CH--, HOCH.sub.2 --CH.sub.2 --, HSCH.sub.2 --CH.sub.2 --, HOCH.sub.2 --, HOOC--, HOCH.sub.2 CH.dbd.CH--, CH.sub.3 CH(OH)-- or HOCH.sub.2 C.sub.* H(Z)--; Y represents --CH.sub.2).sub.n or --CH.sub.2 (.sub.m O).sub.l CH.sub.2 --, where n represents an integer of 1 to 18, m represents an integer of 1 to 12, and l represents an integer of 1 to 4; M and Z each represents halogen atom, an alkyl group or an alkoxy group, said halogen atom being selected from the group consisting of I, Cl, Br and F, and said alkyl group or alkoxy group having 1 to 8 carbon atoms; and the mark * represents an asymmetric carbon atom. A process for preparing the intermediate compound is also disclosed.Type: GrantFiled: August 7, 1990Date of Patent: December 15, 1992Assignees: Canon Kabushiki Kaisha, Hiroyuki NohiraInventors: Hiroyuki Nohira, Takahiro Ishizuka, Kazuo Yoshinaga
-
Patent number: 5122297Abstract: The invention relates to novel tetracyclic benzene derivatives of the formula I ##STR1## in which n is 1 to 7, A is trans-1,4-cyclohexylene, 1,4-phenylene, 3-fluoro-1,4-phenylene or 3,5-difluoro-1,4-phenylene, X is F, Cl, CF.sub.3, --OCF.sub.3 or --OCHF.sub.2, and L, Y and Z are each, independently of one another, H or F.Type: GrantFiled: April 25, 1991Date of Patent: June 16, 1992Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Volker Reiffenrath, Reinhard Hittich, Herbert Plach
-
Patent number: 5082587Abstract: Achiral fluorine-containing liquid crystal compounds are provided. The compounds comprise a fluorocarbon terminal portion and a hydrocarbon or another fluorocarbon terminal portion, the terminal portions being connected by a central core, the compounds having smectic mesophases or having latent smectic mesophases. The compounds are useful in liquid crystal display devices both along and in mixtures with other materials. Also provided is a process for preparing these compounds.Type: GrantFiled: September 23, 1988Date of Patent: January 21, 1992Inventor: Eugene P. Janulis
-
Patent number: 5051506Abstract: Chiral, nonracemic compounds of the general formula: ##STR1## wherein m and n are either both zero, both equal one or n is equal to one and m is equal to zero, X and Y and Z are halogens, R' is an alkyl or alkoxy group having three to fifteen carbons, R is an alkyl group having one to fifteen carbons, and Ar is a 4,4'-substituted phenylvenzoate, 4,4'-substituted biphenylbenzoate, 5,4-substituted 2-phenylpyrimidine or 4,4'-substituted biphenyl core, and wherein * indicates a chiral center, which are useful as ferroelectric liquid crystal components having high polarization are described.Type: GrantFiled: March 4, 1988Date of Patent: September 24, 1991Assignee: Displaytech, Inc.Inventors: Michael D. Wand, David M. Walba
-
Patent number: 4973691Abstract: An etheric derivative of 4(3H)-quinazolinone which is a fluorinated 3-[2-(4-biphenylyloxy)ethyl]-4(3H)-quinazolinone, produced by reacting said 4(3H)-quinazolinone with the corresponding fluorinated 4-(2-chloroethoxy)biphenyl, and its acid addition salts, especially the hydrochloride. This compound possesses substantially higher analgesic activity and lower acute toxicity than aminophenazone, ibuprofen, acetylosalicyclic acid and paracetamol.Type: GrantFiled: November 1, 1989Date of Patent: November 27, 1990Assignee: Spojene Podniky Prozdravotnickou Vyrobu (SPOFA)Inventors: Ludmila Fisnerova, Bohumila Brunova, Eva Maturova, Jaroslava Grimova
-
Patent number: 4939309Abstract: A method for the preparation of biaryl compounds is disclosed which comprises contacting an aryl halide with a tertiary-alkyl organometallic reagent (or the precursor components thereof) in the presence of a catalyst comprising a nickel compound and a coordinating ligand under conditions suitable for the formation of biaryl compound.In an alternative embodiment of the present invention, nickel(0) compounds are prepared from nickel(II) compounds by contacting a nickel(II) compound with a combination of an organophosphine and a bidentate nitrogen-containing coordinating ligand, and a tertiary-alkyl organometallic reagent (or the precursor components thereof) in an aprotic, non-polar, ether-containing solvent system for a time and under conditions suitable for the formation of nickel(0) compound.Type: GrantFiled: May 3, 1989Date of Patent: July 3, 1990Assignee: Eastman Kodak CompanyInventor: Thomas A. Puckette
-
Patent number: 4917817Abstract: An optically active functional compound represented by the following formula (1) is disclosed: ##STR1## wherein R denotes an alkyl group having 1-14 carbon atoms; -X- denotes ##STR2## denotes a single bond, ##STR3## n=0, 1 or 2; and C* denotes an asymmetric carbon atom. The compound of the formula (1) may be produced through an optically active compound of the following formula (2) or (3): ##STR4## The compounds of the above formulas (1)-(3) are all characterized by a trifluoromethyl group providing a large spontaneous polarization attached to an asymmetric carbon atom.Type: GrantFiled: July 21, 1988Date of Patent: April 17, 1990Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Masanao Kamei, Hideki Kanazawa, Tetsuya Abe, Yoko Yamada, Yuko Etoh
-
Patent number: 4916227Abstract: A method for the preparation of biaryl compounds is disclosed which comprises contacting an aromatic halide in the presence of a catalyst comprising zerovalent nickel, a bidentate phosphorus-containing coordinating ligand and a reducing metal in a polar, aprotic solvent system for a time and under conditions suitable for the formation of biaryl compound.Type: GrantFiled: August 3, 1989Date of Patent: April 10, 1990Assignee: Eastman Kodak CompanyInventor: Thomas A. Puckette
-
Patent number: 4914244Abstract: Difluorochloromethoxybenzenes are prepared by reacting phenols with trichloromethyl chloroformate (=di-phosgene) in the presence of hydrogen fluoride.Type: GrantFiled: January 14, 1987Date of Patent: April 3, 1990Assignee: Bayer AktiengesellschaftInventor: Albrecht Marhold
-
Patent number: 4895986Abstract: The invention relates to novel compounds usable as liquid crystals in liquid crystal display devices utilizing the electrically controlled birefringence effect.These compounds comply with formula: ##STR1## in which R.sup.1 represents an alkoxy or alkyl radical with 1 to 12 carbon atoms and Z represents a single bond or a radical chosen from among: ##STR2## provided that R.sup.1 represents an alkyl radical when Z represents a single bond and R.sup.2 represents an alkyl radical with 1 to 12 carbon atoms.They can be obtained by reacting an acid chloride of formula R.sup.Type: GrantFiled: September 15, 1988Date of Patent: January 23, 1990Assignee: Commissariat a l'EnergieInventors: Claude Vauchier, Francoise Vinet
-
Patent number: 4886619Abstract: Compounds are provided which comprise a fluorocarbon terminal portion and a chiral hydrocarbon terminal portion, said terminal portions being connected by a central core, said compounds having tilted smectic mesophases or having latent tilted smectic mesophases which develop when said compounds having said latent mesophases are in admixture with said compounds having tilted smectic mesophases or said compounds having latent tilted smectic mesophases.Type: GrantFiled: May 29, 1987Date of Patent: December 12, 1989Assignee: Minnesota Mining and Manufacturing CompanyInventor: Eugene P. Janulis
-
Patent number: 4879061Abstract: A method of making liquid crystalline compounds of the formula ##STR1## where A represents a cyclohexane ring, n has values of 1, 2 or 3, R1 is an alkyl radical, R2 is an alkyl, alkoxy, or alkylcyclohexyl or cyanide radical, and X1 is lower alkyl and X2, X3 and X4 is alkyl and preferably methyl, ethyl or propyl, hydrogen, halogen and preferably fluorine or cyanide and to the compound.Type: GrantFiled: September 29, 1986Date of Patent: November 7, 1989Assignee: Crystaloid Electronics Co.Inventors: Joseph P. Ferrato, Julie C. Ferrato
-
Patent number: 4877548Abstract: 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: GrantFiled: December 27, 1988Date of Patent: October 31, 1989Assignee: Chisso CorporationInventors: Kisei Kitano, Makoto Ushioda, Manabu Uchida, Toshiharu Suzuki
-
Optically active compound, process for producing same and liquid crystal composition containing same
Patent number: 4873018Abstract: An optically active 2-fluoro-1-alkanol compound represented by the formula (Ia): ##STR1## wherein R is an alkyl group having 1-16 carbon atoms, and C* is an asymmetric carbon atom; and an optically active compound derived from the fluoroalkanol and represented by the formula (Ib): ##STR2## wherein R and C* are the same as above, m is 1 or 2, n is 0 or 1, and A is a releasable substitutent. Because of the fluorine atom directly attached to an asymmetric carbon atom, these compounds are particularly effective in increasing a spontaneous polarization, improving a electric field responsive characteristic of a liquid crystal composition, and controlling the liquid crystal state.Type: GrantFiled: October 27, 1987Date of Patent: October 10, 1989Assignees: Canon Kabushiki Kaisha, Yamakawa Yakuhin Kogyo Kabushiki KaishaInventors: Hiroyuki Nohira, Masanao Kamei, Shinichi Nakamura, Kazuo Yoshinaga, Mariko Kai, Kazuharu Katagiri -
Patent number: 4871470Abstract: 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: GrantFiled: October 30, 1987Date of Patent: October 3, 1989Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Andreas Wachtler, Joachim Krause, Rudolf Eidenschink, Georg Weber
-
Patent number: 4867903Abstract: A fluoroalkane derivative represented by the formula: ##STR1## wherein R denotes an alkyl group having 1-16 carbon atoms, C* denotes an asymmetric carbon atom, R.sup.1 denotes an alkyl or alkoxy group having 1-16 carbon atoms; ##STR2## respectively denote a phenylene group ##STR3## a cyclohexylene group ##STR4## or a pyrimidinylene group ##STR5## p is 0 or 1, q is 0 or 1 when p is 1, r is 0 or 1; and l, m and n are respectively 0 or a positive integer satisfying the relationship of l+m+n.gtoreq.1. The fluoroalkane derivative has a fluorine atom providing a large dipole moment and directly connected to an asymmetric carbon atom, so that it provides a high speed responsive characteristic through an increased spontaneous polarization when contained in a liquid crystal composition, especially a ferroelectric liquid crystal composition.Type: GrantFiled: March 6, 1987Date of Patent: September 19, 1989Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Masanao Kamei, Shinichi Nakamura, Kazuharu Katagiri
-
Patent number: 4853151Abstract: 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: GrantFiled: August 11, 1987Date of Patent: August 1, 1989Assignee: Merck Patent Gesellschaft Mit Beschrankfter HaftungInventors: Fritz Vogtle, Wolfgang Calaminus
-
Patent number: RE36849Abstract: 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: GrantFiled: April 1, 1993Date of Patent: September 5, 2000Assignee: Merck Patent GmbHInventors: Hans P. Schad, Stephen M. Kelly, Eike Poetsch, Reinhard Hittich, Georg Weber