Halogen In Acid Moiety Patents (Class 560/65)
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Patent number: 5972243Abstract: A ferrielectric liquid crystal compound of the following general formula (1), ##STR1## wherein R is a linear alkyl group having 6 to 12 carbon atoms; X is a hydrogen atom or a fluorine atom; m and n are the same or different from each other, each being an integer of 1 to 3; and C* is an asymmetric carbon atom,the ferrielectric liquid crystal compound being remarkably valuable as a raw material for a liquid crystal display device since it shows a ferrielectric phase in a broad temperature range and shows a high-speed response in spite of its small spontaneous polarization.Type: GrantFiled: July 23, 1998Date of Patent: October 26, 1999Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takakiyo Mine, Masahiro Johno, Tomoyuki Yui, Yasue Yoshioka
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Patent number: 5968413Abstract: Novel anti-ferroelectric liquid crystal compounds of the formula (1), ##STR1## wherein R is a linear alkyl group having 6 to 12 carbon atoms, X is a hydrogen atom or a fluorine atom, n is an integer of 2 to 7, p is an integer of 0 to 2 and C* is an asymmetric carbon atom. The above anti-ferroelectric liquid crystal compounds have an anti-ferroelectric phase in a broad temperature range and have a low melting point, so that they can be advantageously used as a main component for a practically valuable liquid crystal material or as a component for a liquid crystal composition.Type: GrantFiled: January 27, 1998Date of Patent: October 19, 1999Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takakiyo Mine, Tomoyuki Yui, Masahiro Johno, Hiroshi Mineta
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Patent number: 5938973Abstract: A swallow-tailed compound of the following general formula (1), ##STR1## wherein m is an integer of 4 to 10, n is an integer of 2 to 6, p is 0 or 1 and each of X and Y is independently a hydrogen or fluorine atom; and a ferrielectric liquid crystal composition consisting essentially of the swallow-tailed compound of the general formula (1) and a ferrielectric liquid crystal compound of the following general formula (2), ##STR2## wherein R is a linear alkyl group having 6 to 12 carbon atoms, Z is a hydrogen or fluorine atom, r is an integer of 2 to 4 and s is an integer of 2 to 4. The ferrielectric liquid crystal composition has a ferrielectric phase in a broad temperature range and attains a fast response and a large tilt angle in a broad temperature range so that a ferrielectric liquid crystal display device having high display qualities can be provided.Type: GrantFiled: September 11, 1997Date of Patent: August 17, 1999Assignee: Mitsubishi Gas Chemical CompanyInventors: Yuki Motoyama, Tomoyuki Yui, Masahiro Johno, Takahiro Matsumoto
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Patent number: 5874608Abstract: The present invention relates to a process for the preparation of compounds of the formula (1)R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOR (1)in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms or OR, NHR, NR.sub.2, SR or COOR, in which R is an alkyl radical having 1 to 4 carbon atoms, Ar is an aryl radical having 6 to 12 carbon atoms and the radical R shown in formula (1) has the above meaning, by reacting a compound of the formula (2)R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOH (2)in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms, OH, NH.sub.2, NHR, SH or COOH and Ar has the same meaning as in formula (1), with a sulfate of the formula (RO).sub.2 SO.sub.2, in which R has the above meaning, in the presence of a water-insoluble tertiary amine and water at a temperature of 10.degree.Type: GrantFiled: May 19, 1997Date of Patent: February 23, 1999Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Theodor Papenfuhs
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Patent number: 5861109Abstract: Liquid crystal compounds of formula I may be used by themselves or they may be mixed with other liquid crystal compounds to give useful liquid crystal mixtures which may then be used in liquid crystal devices. The materials exhibit smectic mesophases and may therefore be used in ferroelectric, ferrielectric, antiferroelectric, themochromic and electroclinic devices. They may also be used as long pitch materials.Type: GrantFiled: January 24, 1996Date of Patent: January 19, 1999Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland of Defence Evaluation Research AgencyInventors: John W. Goodby, Peter Styring, Christa Loubser, Philippus L Wessels
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Patent number: 5851424Abstract: The present invention is concerned with photo cross-linkable liquid crystalline compounds of the general formula ##STR1## wherein A.sup.1 and A.sup.2 each represent a cross-linkable, mesogenic residue,liquid crystalline mixtures which contain such compounds and their use in the cross-linked state as optical components.Type: GrantFiled: July 25, 1996Date of Patent: December 22, 1998Assignee: Rolic AGInventor: Stephen Kelly
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Patent number: 5840209Abstract: ?I! An optically active compound of the formula (1), ##STR1## wherein R.sup.1 is a linear alkyl group, each of X.sup.1 and X.sup.2 is a hydrogen atom or one of X.sup.1 and X.sup.2 is a hydrogen atom and the other is a fluorine atom, each of Y.sup.1 and Y.sup.2 is a hydrogen atom or one of Y.sup.1 and Y.sup.2 is a hydrogen atom and the other is a fluorine atom, m is an integer of 3 to 10, and C* is an asymmetric carbon atom,?II! an anti-ferroelectric liquid crystal composition consisting essentially of the optically active compound of the above formula (1) and a compound of the formula (2), ##STR2## and ?III! a ferrielectric liquid crystal composition consisting essentially of the optically active compound of the formula (1) and a compound of the formula (3).Type: GrantFiled: May 14, 1997Date of Patent: November 24, 1998Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hiroshi Mineta, Tomoyuki Yui, Masahiro Johno, Seiji Adachi, Yuki Motoyama
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Patent number: 5817862Abstract: The invention relates to a process for the preparation of cinnamic acid derivatives which involves reacting chlorinated aromatic compounds and acrylic acid derivatives in the presence of palladium catalysts.Type: GrantFiled: August 22, 1996Date of Patent: October 6, 1998Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Eike Poetsch, Volker Meyer, Ulrich Heywang, Rainer Christ, Jurgen Seubert
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Patent number: 5800734Abstract: A compound of the formula ##STR1## wherein R is C.sub.1 -C.sub.7 alkyl or C.sub.2 -C.sub.12 alkenyl; rings A and B each independently are 1,4-phenylene,trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl;Z.sup.1 is a single bond or --CH.sub.2 CH.sub.2 --; andZ.sup.2 is a single bond, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --,--C.tbd.C--, --COO-- or --OOC--; andm, n are 0 or 1, with the proviso that m+n.ltoreq.1;as well as liquid crystalline mixtures which contain such compounds and the use of such compounds and, respectively, mixtures for electro-optical display devices.Type: GrantFiled: March 4, 1996Date of Patent: September 1, 1998Assignee: Rolic AGInventors: Richard Buchecker, Guy Marck
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Patent number: 5800733Abstract: The present invention is concerned with photo cross-linkable liquid crystalline compounds in the formula ##STR1## wherein for example: A,B,C,D,E,F independently is pyridine-2,5-diyl, pyrimidine-2,5-diyl, trans-1,4-cyclohexylene, trans-1,3-dioxane-2,5-diylZ.sup.1, Z.sup.2, Z.sup.7 independently is --(CH.sub.2).sub.s O--, --COO--, --(CH.sub.2).sub.s COO--Z.sup.3, Z.sup.4, Z.sup.8 independently is a single bond, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--Z.sup.5, Z.sup.6 independently is --(CH.sub.2).sub.s --m, n, q and r independently is 0, 1 or 2;s is a whole number of 1 to 16;R.sup.1, R.sup.2 independently is CH.sub.2 .dbd.CH--COO--, CH.sub.2 .dbd.C(CH.sub.3)--COO--R.sup.3 is H, CH, COOC.sub.n H.sub.2n+1, CnH.sub.2n+1 ; n=1 . . . 10X.sup.1, X.sup.2 and X.sup.3 independently is hydrogen, halogen, cyano or lower alkyl.The invention is also related to liquid crystalline mixtures and their use for electro-optical purpose.Type: GrantFiled: July 25, 1996Date of Patent: September 1, 1998Assignee: Rolic AGInventor: Stephen Kelly
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Patent number: 5798058Abstract: Compounds of formula (I) which are suitable for use in liquid crystal devices including those devices which exploit the electroclinic effect. The compounds of formula (I) may also be used as chiral dopoants suitable for use with ferroelectric liquid crystals or they may be used as chiral nematic dopants.Type: GrantFiled: December 31, 1996Date of Patent: August 25, 1998Assignee: Secretary of State for Defence in her Britannic Majesty's Government of the United Kingdom of Gt. Britain & N. Ireland of Defence Evaluation and Research AgencyInventors: John William Goodby, Kenneth Johnson Toyne, Michael Hird, Robert Andrew Lewis
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Patent number: 5792876Abstract: A process is described for producing acetals comprising reacting an aldehyde or a ketone with an alcohol in the presence of a titanium compound having an acetylacetone as a ligand, or in the presence of a compound selected from the group consisting of stannous chloride dihydrate, cerium chloride hexahydrate and bismuth chloride. The process can be used in the synthesis of unstable acetals or when water exists in the reaction mixture, and therefore the process can be used for a wide variety of applications.Type: GrantFiled: November 6, 1996Date of Patent: August 11, 1998Assignee: Kuraray Co., Ltd.Inventors: Hideharu Iwasaki, Masahiko Kitayama, Takashi Onishi
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Patent number: 5755994Abstract: A novel liquid crystalline compound having a large dielectric anisotropy value, a small change in the threshold voltage depending upon temperatures, and an improved solubility in other liquid crystal materials at low temperatures, and a liquid crystal composition containing the compound are provided,which liquid crystalline compound is expressed by the formula (1) ##STR1## wherein R is H or an alkyl group of 1 to 10C; l is an integer of 1 to 9; m, n and o are each independently 0 or 1; A.sub.1, A.sub.2 and A.sub.3 are each independently trans-1,4-cyclohexylene group, 1,4-phenylene group, one or more H atoms on the ring of which group may be replaced by F, or the like group; Z.sub.1, Z.sub.2 and Z.sub.3 are each independently --COO--, etc., but at least one of them is --COO--; X is CF.sub.3, etc.; and Y.sub.1, and Y.sub.2 are each independently H or F.Type: GrantFiled: February 22, 1996Date of Patent: May 26, 1998Assignee: Chisso CorporationInventors: Tomoyuki Kondo, Shuichi Matsui, Yasuyuki Koizumi, Koichi Shibata, Yasuhiro Haseba, Norihisa Hachiya, Etsuo Nakagawa, Kazutoshi Miyazawa
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Patent number: 5755997Abstract: Compounds of the following formula exhibit broad chiral smectic C phases and have excellent stability: ##STR1## wherein R represents a hydrocarbon group having 1 to 14 carbon atoms, X is a halogen atom, and R.sup.1 represents a branched alkyl group having 3 to 8 carbon atoms.Type: GrantFiled: October 3, 1996Date of Patent: May 26, 1998Assignee: Samsung Display Devices Co., Ltd.Inventor: Bagavant Shivkumar
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Patent number: 5756814Abstract: (1) CF.sub.2 .dbd.CFO(CF.sub.2).sub.n COOR is allowed to react with chlorine or bromine to obtain CF.sub.2 XCFXO(CF.sub.2).sub.n COOR', (2) which is allowed to react with a Grignard reagent MgBrC.sub.6 H.sub.3 (CH.sub.3).sub.2 to convert the terminal group to --COC.sub.6 H.sub.3 (CH.sub.3).sub.2, (3) followed by reaction with diethylaminosulfur trifluoride to convert --COC.sub.6 H.sub.3 (CH.sub.3).sub.2 to --CF.sub.2 C.sub.6 H.sub.3 (CH.sub.3).sub.2, (4) followed further by oxidation of the resulting methyl group and by esterification to convert the methyl group to --CF.sub.2 C.sub.6 H.sub.3 (COOR).sub.2 and (5) followed by dechlorination or debromination to obtain CF.sub.2 .dbd.CFO(CF.sub.2).sub.n CF.sub.2 C.sub.6 H.sub.3 (COOR).sub.2. The resulting bifunctional vinyl ether compound having an aromatic ring is a novel compound and can be used as a copolymer component for fluorine-containing elastomers.Type: GrantFiled: June 23, 1997Date of Patent: May 26, 1998Assignee: Nippon Mektron, LimitedInventors: Leng-Tain Lin, Kenji Iimura, Takehiro Sonoi
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Patent number: 5744628Abstract: The present invention relates to a process for the preparation of compounds of the formula (1)R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOR (1)in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms, OR, NHR, NR.sub.2, SR or COOR, R being an alkyl radical having 1 to 4 carbon atoms, Ar is an aryl radical having 6 to 12 carbon atoms and the radical R identified in formula (1) has the above meaning, by reacting a compound of the formula (2)R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOH (2)in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms, OH, NH.sub.2, NHR, SH or COOH and Ar has the same meaning as in formula (1), with a sulfate of the formula (RO).sub.2 SO.sub.Type: GrantFiled: July 29, 1996Date of Patent: April 28, 1998Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Theodor Papenfuhs
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Patent number: 5744058Abstract: Dienes of the formula I ##STR1## in which n is 0, 1, 2, 3, 4 or 5,r is 1, 2 or 3,s is 1 or 2, ##STR2## is trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl, ##STR3## is trans-1,4-cyclohexylene, trans-1,3-dioxane-2,5-diyl, unfluorinated or mono- or polyfluorinated 1,4-phenylene, in which one or two CH groups may also be replaced by N, or the central part ##STR4## Z is a single bond, a bridging member selected from the group consisting of --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C--, --CO--O--, --CH.sub.2 O--, --OCH.sub.2 -- and --O--CO--, or any desired combination of two such bridging members, where two O atoms are not linked directly to one another, andR is --CN, --NCS, halogen or an alkyl, alkenyl, alkoxy or alkenyloxy group, in each case having up to 12 carbon atoms and in each case unsubstituted or monosubstituted or polysubstituted by fluorine and/or chlorine.Type: GrantFiled: June 2, 1995Date of Patent: April 28, 1998Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Volker Reiffenrath, Bernhard Rieger
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Patent number: 5728864Abstract: A liquid crystal compound of the formula (1) ##STR1## wherein R is a linear alkyl group having 6 to 12 carbon atoms,both X and Y are hydrogen atoms or one of X and Y is a fluorine atom and the other is a hydrogen atom,A is --CF.sub.3 or --C.sub.2 F.sub.5,m is an integer of 2 to 4,n is an integer of 2 to 4, andC* is an asymmetric carbon,having a ferrielectric phase in its phase sequence, or a ferrielectric liquid crystal composition containing the liquid crystal compound of the formula (1) having a ferrielectric phase, may be injected between substrates provided with nonlinear active elements, such as thin film transistors or diodes formed on each pixel, to form an active matrix liquid crystal display device.Type: GrantFiled: April 12, 1996Date of Patent: March 17, 1998Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Yuki Motoyama, Tomoyuki Yui, Masahiro Johno, Maki Ito, Takahiro Matsumoto, Hiroshi Mineta
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Patent number: 5728323Abstract: A process for the preparation of dialkyl tetrahalophthalates. A tetrahalophthalic anhydride or acid is dissolved in excess C.sub.1 -C.sub.18 alkanols. Residual sulfuric acid is removed by treatment with magnesium acetate or multiple water washes. The mass is esterified with a tetraalkyl titanate, and residual acidic components are removed by treatment with magnesium silicate. These treatments improve processability, production cycle time, product color, clarity and purity.Type: GrantFiled: November 6, 1995Date of Patent: March 17, 1998Assignee: Unitex Chemical CorporationInventors: James F. Day, James J. Good
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Patent number: 5723069Abstract: An anti-ferroelectric liquid crystal compound of the following general formula (1), and an anti-ferroelectric liquid crystal composition containing it, ##STR1## wherein R is a linear alkyl group, A is --O-- or --COO--, m is an integer of 5 or greater, n is an integer of 1 to 3, each of X and Y is independently a hydrogen atom or a fluorine atom, and C* is asymmetric carbon.Type: GrantFiled: December 17, 1996Date of Patent: March 3, 1998Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hiroshi Mineta, Tomoyuki Yui, Masahiro Johno, Teruyo Tomiyama
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Patent number: 5719309Abstract: A process for preparing 4-bromomethyl-3-methoxybenzoic esters of the formula ##STR1## entails the corresponding 4-methyl-3-methoxybenzoic esters being reacted in chlorobenzene or an ester as solvent with N-bromosuccinimide with exposure to light of wavelength 10.sup.-5 to 10.sup.-8 m at -10.degree. to 120.degree. C.Type: GrantFiled: August 26, 1996Date of Patent: February 17, 1998Assignee: Hoechst AktiengesellschaftInventors: Dieter Regnat, Hans-Jerg Kleiner
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Patent number: 5707544Abstract: The present invention is concerned with chromophore-containing photo cross-linkable liquid crystalline compounds having the formula ##STR1## wherein A.sup.1 and A.sup.2 each represent a cross-linkable, mesogenic group; andA.sup.3 represents a dichroic group.as well as liquid crystalline mixtures which contain such compounds and their use in the cross-linked state as optical components.Type: GrantFiled: May 20, 1996Date of Patent: January 13, 1998Assignee: Rolic AGInventor: Stephen Kelly
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Patent number: 5702637Abstract: Fluorine-containing, chiral liquid crystal compounds comprise (a) a chiral fluorochemical terminal portion containing at least one methylene group and optionally containing at least one catenary ether oxygen atom; (b) a saturated, chiral or achiral, 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: April 19, 1995Date of Patent: December 30, 1997Assignee: Minnesota Mining and Manufacturing CompanyInventors: Gilbert C. Johnson, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
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Patent number: 5700393Abstract: The present invention is concerned with photo cross-linkable liquid crystalline compounds of the general formula ##STR1## wherein A.sup.1 and A.sup.2 each are a cross-linkable mesogenic residue; andA.sup.3 is (R,R)- or (S,S)-trans-1,2-cyclohexyl-diyl,liquid crystalline mixtures which contain such compounds and their use in the cross-linked state as optical components.Type: GrantFiled: July 26, 1996Date of Patent: December 23, 1997Assignee: Rolic AGInventor: Stephen Kelly
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Patent number: 5686633Abstract: Inks, particularly inks for ink jet printing, contain at least one compound of the formula I ##STR1## as a stabilizer. The symbols R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.3 ' and R.sub.4 ' are as defined in claim 1. The compounds are in part novel and are suitable for use as light stabilizers for organic materials.Type: GrantFiled: December 31, 1991Date of Patent: November 11, 1997Assignee: Ciba Specialty Chemicals CorporationInventors: Eric Vieira, Hugh Stephen Laver
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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
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Patent number: 5658493Abstract: This invention provides chiral, non-racemic compounds and liquid crystal compositions comprising such compounds. The compounds of this invention include those having the formula: ##STR1## wherein k=0 or 1 and when k=1, B=COO, OOC, --C.tbd.C--, or --C.tbd.C--C.tbd.C--; X.sub.1, X.sub.2, X.sub.3 and X.sub.4 are either H, an electron donor or an electron acceptor where at least one of the groups X.sub.1, X.sub.2, X.sub.3 or X.sub.4 is an electron acceptor and at least one of these groups is an electron donor or H and when one of X.sub.1 or X.sub.3 is an electron donor or H, the other is an electron acceptor and when one of X.sub.2 or X.sub.4 is an electron donor or H, the other is an electron acceptor; and R.sub.1 and R.sub.2 can be various substituted and unsubstituted alkanes and monoalkenes. Compounds provided include those where one of R.sub.1 or R.sub.2 is a chiral non-racemic tail group, particularly a group selected from --O--C*H(CH.sub.3)R.sub.c, --O--C*H(CH.sub.3)COOR.sub.d, and --O--CH.sub.Type: GrantFiled: May 26, 1995Date of Patent: August 19, 1997Assignee: University Research CorporationInventors: David M. Walba, Maria Blanca Ros, James A. Rego, Teresa Sierra
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Patent number: 5648021Abstract: This invention relates to novel phenanthrene derivatives of the formula (I) which are particularly suitable for use in liquid-crystal mixtures. The compounds of formula (I) have a broad range of applications. Depending on the choice of substituents, they can be used as base materials from which liquid-crystalline phases are predominantly composed. They can also be added to liquid-crystalline base materials to modify the dielectric and/or optical anisotropy of a dielectric and to optimize its threshold voltage or viscosity. Liquid-crystalline mixtures containing compounds of formula (I) are particularly suitable for use in electrooptical switching and display devices.Type: GrantFiled: January 13, 1995Date of Patent: July 15, 1997Assignee: Hoechst AktiengesellschaftInventors: Rainer Wingen, Barbara Hornung
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Patent number: 5643495Abstract: 1,2,2,2-Tetrafluoroethyl ethers of the formula IR--(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --Z.sup.2 A.sup.3 --O--CHF--CF.sub.3(I)are suitable as components of liquid-crystalline media whereinR is H, a substituted or unsubstituted alkyl or alkenyl radical having 1 to 15 carbon atoms,A.sup.1 and A.sup.2 are each, independently of one another, a(a) trans-1,4-cyclohexylene radicals and derivatives thereof in which, in addition, one or more non-adjacent CH.sub.2 groups is optionally replaced by --O-- and/or --S--,(b) 1,4-phenylene radicals and derivatives thereof in which, in addition, one or two CH groups is optionally replaced by N, or(c) radical from the group consisting of 1,4-cyclohexenylene, 1,4-bicyclo(2,2,2)octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl,wherein radicals (a) and (b) are optionally substituted by one or two fluorine atoms,Z.sup.1 and Z.sup.2 are each, independently of one another, --CO--O--, --O--CO--, --CH.sub.Type: GrantFiled: September 12, 1995Date of Patent: July 1, 1997Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Ekkehard Bartmann, Ulrich Finkenzeller
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Patent number: 5597943Abstract: The present invention relates to the new thielocin derivatives, which exhibit phospholipase A.sub.2 inhibitory activity of the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, and R.sup.8 are independently hydrogen, lower alkyl, lower alkoxy, hydroxy, or halogen;E.sub.1 and E.sub.2 are independently hydrogen, or an ester residue;m and n are independently an integer of 0 to 4;--Y-- is a bivalent group which is selected from the group consisiting of the following radicals: ##STR2## or the salts thereof.Type: GrantFiled: December 13, 1995Date of Patent: January 28, 1997Assignee: Shionogi & Co., Ltd.Inventors: Mitsuaki Ohtani, Shigeru Matsutani, Tadashi Yoshida, Kazushige Tanaka, Yasuhiko Fujii, Kazuhiro Shirahase
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Patent number: 5536442Abstract: The invention relates to liquid crystal compounds having a terminal structure in accordance with formula 1, 2, 3 or 4:--A.sup.3 --OCF.sub.3 1--A.sup.2 --Q--CHF.sub.2 2--3,5-difluoro-1,4-phenylene-X.sup.1 3--3-fluoro-1,4-phenylene-X.sup.2 4wherein A.sup.2, A.sup.3, X.sup.1 and X.sup.2 and are defined herein. The invention further relates liquid crystal phases containing the above components as well as electrooptical displays containing same.Type: GrantFiled: July 6, 1992Date of Patent: July 16, 1996Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Volker Reiffenrath, Hans A. Kurmeier, Eike Poetsch, Herbert Plach, Ulrich Finkenzeller, Ekkehard Bartmann, Joachim Krause, Bernhard Scheuble, Dieter Dorsch, Georg Weber
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Patent number: 5516931Abstract: A release tag reagent suitable for use in the chemical analysis of a substance to be detected comprises signal, release, and reactivity groups. A class of release tag compounds that are cleaved to release as signal groups very stable electrophoric ketones which are sufficiently volatile for determination in the gas phase of an analytical reaction mixture is disclosed.Type: GrantFiled: April 22, 1993Date of Patent: May 14, 1996Assignee: Northeastern UniversityInventors: Roger W. Giese, Samy Abdel-Baky, Linxiao Xu
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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
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Patent number: 5481013Abstract: Compounds of the formula ##STR1## in which A is oxygen, sulfur or --NR.sub.1 --;B is C.sub.2 -C.sub.6 alkylene,D-E is --O--E, --S--E, --O--CH.sub.2 --E, --O--C(.dbd.O)--E, --O--C(.dbd.O)--O--E, --O--C(.dbd.O)--N(H)--E or --O--C(.dbd.S)--N(H)--E;E is phenyl; phenyl which is substituted by one to three substituents; a five-membered aromatic heterocycle having one to three hetero atoms; a five-membered aromatic heterocycle which has one to three hetero atoms and which is substituted by one or two substituents; a six-membered aromatic heterocycle which has one to three nitrogen atoms; or a six-membered aromatic heterocycle which has one to three nitrogen atoms and which is substituted by one or two substituents;L is halogen or methyl;X is fluorine;Y is chlorine or fluorine;Z is hydrogen, fluorine or methyl;m is the number zero, one, two, three, four or five;n is the number zero, one or two andR.sub.1 is hydrogen, C.sub.1 -C.sub.Type: GrantFiled: June 23, 1993Date of Patent: January 2, 1996Assignee: Ciba-Geigy CorporationInventors: Peter Maienfisch, Thomas Pitterna, Manfred Boger
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Patent number: 5474705Abstract: Fluorine-containing, chiral liquid crystal compounds comprise (a) an aliphatic fluorocarbon terminal portion containing at least two catenary ether oxygen atoms; (b) a chiral, 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: November 14, 1994Date of Patent: December 12, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventors: Eugene P. Janulis, Gilbert C. Johnson, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
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Patent number: 5474707Abstract: A cyclic hydrocarbon derivative represented by formula (I): ##STR1## wherein each of Y.sup.1 and Y.sup.2 is independently F, Cl, CN, OCN, SCN, OCF.sub.3, OCF.sub.2 H, OCF.sub.2 CF.sub.3, CF.sub.3, R, --OR, --COOR or --OCOR, wherein R is alkyl, alkenyl or alkoxyalkyl, provided that at least one of Y.sup.1 and Y.sup.2 is R, --OR, --COOR or --OCOR; each of Z, Z.sup.1, Z.sup.2, Z.sup.3 and Z.sup.4 is independently a single bond, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C--, --COO--, --OCO--, --CH.sub.2 O--, OCH.sub.2 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.3 --O-- or --O--(CH.sub.2).sub.3 --; ring A is group of formula (II): ##STR2## wherein each of X.sup.1, X.sup.2, X.sup.3, X.sup.4, X.sup.5, X.sup.6, X.sup.7, X.sup.8, X.sup.9, and X.sup.Type: GrantFiled: July 21, 1994Date of Patent: December 12, 1995Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Haruyoshi Takatsu, Sadao Takehara, Kiyohumi Takeuchi, Masashi Osawa, Shinji Ogawa, Norie Ishida
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Patent number: 5468897Abstract: Bi-aromatic esters have the formula ##STR1## wherein R.sub.1 represents H, OH, --CH.sub.3, --CH.sub.2 OH, --CH(OH)CH.sub.3, --COOR.sub.9, ##STR2## or SO.sub.2 R.sub.10 ; R.sub.9 represents H, C.sub.1 -C.sub.6 alkyl or mono or polyhydroxyalkyl; R.sub.10 represents OH, C.sub.1 -C.sub.6 alkyl or ##STR3## r' and r" represent H, C.sub.1 -C.sub.6 alkyl, aryl, aralkyl, mono or polyhydroxyalkyl, or r' and r" taken together form a heterocycle; R.sub.2 represents H, C.sub.1 -C.sub.6 alkyl, OR.sub.9, F or --CF.sub.3 ; R.sub.3, R.sub.4 and R.sub.5 represent H, F, OH, --CH.sub.3, --OCH.sub.3, --CF.sub.3, --COOH or --CH.sub.2 OH; R.sub.6 and R.sub.8 represent H, .alpha.-substituted C.sub.3 -C.sub.15 alkyl, .alpha., .alpha.'-disubstituted C.sub.4 -C.sub.12 alkyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.12 mono or polycyclic cycloalkyl whose linking carbon is trisubstituted, --SR.sub.11, --SO.sub.2 R.sub.11 or --SOR.sub.11 ; R.sub.11 represents C.sub.1 -C.sub.6 alkyl or cycloalkyl; R.sub.6 and R.sub.Type: GrantFiled: May 4, 1994Date of Patent: November 21, 1995Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)Inventors: Braham Shroot, Jean-Michel Bernardon, William R. Pilgrim
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Patent number: 5458806Abstract: Fluoromethyl ketones of the formula I ##STR1## are suitable as components of liquid-crystalline media wherein R is H, a substituted or unsubstituted alkyl or alkenyl radical having 1 to 15 carbon atoms,A.sup.1 and A.sup.2 are each, independently of one another, a(a) trans-1,4-cyclohexylene radicals and derivatives thereof in which, in addition, one or more non-adjacent CH.sub.2 groups is optionally replaced by --O-- and/or --S--,(b) 1,4-phenylene radicals and derivatives thereof in which, in addition, one or two CH groups is optionally replaced by N, or(c) radical from the group consisting of 1,4-cyclohexenylene, 1,4-bicyclo(2,2,2)octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl,wherein radicals (a) and (b) are optionally substituted by one or two fluorine atoms,Z.sup.1 and Z.sup.2 are each, independently of one another, --CO--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.Type: GrantFiled: May 4, 1994Date of Patent: October 17, 1995Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ekkehard Bartmann, Herbert Plach
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Patent number: 5442092Abstract: An improved process for the preparation of esters of 3,5,6-trichlorosalicylic acid which comprises reacting the acid with an alcohol under distillation conditions in the presence of a catalyst comprising a glycol titanate or glycol stannate. The process results in substantially quantitative yields of the ester without any significant side reactions, e.g. conversion of the alcohol to by-product ether.Type: GrantFiled: April 4, 1994Date of Patent: August 15, 1995Assignee: Jame Fine Chemicals, Inc.Inventors: Vilas M. Chopdekar, James R. Schleck
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Patent number: 5430173Abstract: The present invention relates to a process for preparing alkyl 3-hydroxy-2,4,5-trifluorobenzoate and/or alkyl 3-alkoxy-2,4,5-trifluorobenzoate by reacting 3-hydroxy-2,4,5-trifluorobenzoic acid with a dialkyl carbonate at 80.degree. to 200.degree. C.Type: GrantFiled: September 15, 1994Date of Patent: July 4, 1995Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Theodor Papenfuhs
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Patent number: 5417885Abstract: An antiferroelectric liquid crystal compound of the following formulae: ##STR1## wherein R.sup.1 and R.sup.2 each is an alkyl group of C.sub.4 - C.sub.18, Rf is CF.sub.3 or C.sub.2 F.sub.5, X is O, COO, or a single bond, and * shows an optically active carbon atom.Type: GrantFiled: August 3, 1993Date of Patent: May 23, 1995Assignee: Showa Shell Sekiyu Kabushiki KaishaInventors: Yoshiichi Suzuki, Takashi Hagiwara, Ichiro Kawamura
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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
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Patent number: 5387718Abstract: Alkylphenyl alkyl ethers or alkylphenyl alkyl thioethers, of the formula ##STR1## where U represents O or S; and R.sub.1 -R.sub.6 each independently represent an alkyl or aryl group with 1-6 C atoms, but R.sub.1 -R.sub.5 may each independently represent a functional group other than these, particularly --COOR (R=C.sub.1-4 alkyl), --NO.sub.2, --NH.sub.2, --O--CH.sub.2 --CH.sub.2 --OH, --OH, --CHO, --H, or -halogen;R.sub.1 -R.sub.5 may be bridged by suitable bifunctional substituents, such as, e.g., --(CH.sub.2).sub.x --, or --(CH.sub.2).sub.x --Z--(CH.sub.2).sub.y -- (where Z represents a hetero atom; x=0-7 and y=0-7), or by unsaturated substituents or anellated ring systems; may be produced in high space-time yield by reacting the corresponding phenol or thiophenol with a arylalkyl carbonate at a temperature of 70.degree.-300.degree. C. under elevated or normal pressure, in the presence of a monocyclic, bicyclic, polycyclic, or acyclic amidine as a catalyst.Type: GrantFiled: July 14, 1992Date of Patent: February 7, 1995Assignee: Huels AktiengesellschaftInventors: Gunther Kohler, Peter Bickert
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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
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Patent number: 5380915Abstract: A liquid-crystalline copolymer comprising the repeating units represented by the following general formulas ##STR1## wherein each of r and p is an integer of 2 to 5, q is an integer of 0 to 3, m is an integer of 1 to 20, and R.sup.1 is ##STR2## R.sup.2 being --COOR.sup.3, --OR.sup.3 or --OCOR.sup.3 R.sup.3, ##STR3## each of R.sup.4 and R.sup.5 being --CH.sub.3 or a halogen atom, each of a and d being an integer of 0 to 10, b being an integer of 0 or 1, with the proviso that d is not 0 when R.sup.5 is --CH.sub.3, the repeating units [I] and [II] being present in the liquid-crystalline copolymer in a substantial molar ratio [I]:[II] of 1:1, exhibits ferroelectricity even at a temperature neighboring room temperature and having a high response speed to changes of external electric fields.Type: GrantFiled: May 26, 1993Date of Patent: January 10, 1995Assignee: Idemitsu Kosan Co., Ltd.Inventors: Kazuharu Morita, Satoshi Hachiya, Fumio Moriwaki, Hiroyuki Endo
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Patent number: 5374376Abstract: Disclosed are herein optically active aromatic compounds represented by the formula (I): ##STR1## wherein X represents --COO-- or --OCO--; Y represents --COO--, --OCO-- or --O--; R.sub.2 represents an alkyl or alkoxyalkyl group having 1 to 20 carbon atoms unsubstituted or substituted by a halogen atom; R.sub.1 represents an alkyl group having 3 to 20 carbon atoms;Z represents ##STR2## wherein p represents a number of 1 to 5 and * indicates an asymmetric carbon atom; l and k each represents a number of 1 or 2; m and s each represents a number of 0 or 1, which are useful as a liquid crystal.Type: GrantFiled: September 21, 1993Date of Patent: December 20, 1994Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Higashii, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Shigeaki Chika, Koichi Fujisawa, Kiyoshi Imamura
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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
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Patent number: 5364560Abstract: An antiferroelectric liquid crystal compound which is a compound represented by ##STR1## wherein R denotes a linear aliphatic alkyl group having 6 to 14 carbon atoms; A denotes a single bond or an oxygen atom; X and Y independently denote a hydrogen atom or a fluorine atom but they are not hydrogen atoms at the same time; h and i are independently 1 or 2; m is an integer of 3 to 10; Z denotes CH.sub.3, C.sub.2 H.sub.5 or CF.sub.3 ; k is 0 or an integer of 5 to 8; l is 0 or 1; n is an integer of 1 to 6; W denotes CH.sub.3 or CF.sub.3 ; when W is CH.sub.3, p and q are both 0 and r is 8; when W is CF.sub.3, p is 5 to 8, q is 1 and r is 1 to 4; and C* denotes an asymmetric carbon atom,and a liquid crystal display device using same.Type: GrantFiled: January 29, 1992Date of Patent: November 15, 1994Assignee: Mitsubishi Gas Chemical Co., Inc.Inventors: Masamichi Mizukami, Tomoyuki Yui, Masahiro Johno, Yoshihisa Arai, Hiroshi Mineta
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Patent number: 5344958Abstract: Insecticidal compounds having the formula N-(2-R.sup.a -3-R.sup.b -benzoyl)-N'-(2-R.sup.c -3-R.sup.d -4-R.sup.e -5-R.sup.f -benzoyl)-N'-R.sup.g -hydrazine, where R.sup.a is a halogen or a lower alkyl; R.sup.b is lower alkoxy; R.sup.c-f are selected from hydrogen, bromo, chloro, fluoro, lower alkyl and lower alkoxy; and Rg is a (C.sub.4 -C.sub.6)alkyl or (C.sub.4 -C.sub.6)alkenyl; as well as compositions comprising an agronomically acceptable carrier and an insecticidally effective amount of such compounds; and methods of using such compounds and compositions.Also, methods for the production of the compounds and their intermediates, which methods comprise admixing a 3-amino-2-(substituted)-benzoic acid, sodium nitrite and methanol under acidic conditions.Type: GrantFiled: November 23, 1992Date of Patent: September 6, 1994Assignee: Rohm and Haas CompanyInventors: Zev Lidert, Dat P. Le
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Patent number: 5340498Abstract: A novel anti-ferroelectric liquid crystal of the formula (I), ##STR1## wherein: is an integer of 3 to 8,each of X and Y is independently a hydrogen atom or a fluorine atom,Z is --CF.sub.3, --CH.sub.3 or --C.sub.2 H.sub.5,q is 0 or 5,m is 0 or 1,n is an integer of 2 to 8, andC* is an asymmetric carbon, provided that when m is 0, q is 0 and n is an integer of 4 to 8 and that when m is 1, q is 5 and z is --CF.sub.3,and use of tile above liquid crystal as a liquid crystal display device.Type: GrantFiled: August 19, 1993Date of Patent: August 23, 1994Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Yoshihisa Arai, tomoyuki Yui, Yoshihiro Gocho