Ring In Alcohol Moiety Patents (Class 560/73)
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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
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Patent number: 4886623Abstract: A liquid crystal compound represented by formula: ##STR1## wherein R.sub.1 represents a straight chain alkyl group having from 4 to 18 carbon atoms; R.sub.2 represents a straight chain alkyl group having from 2 to 6 carbon atoms or a branched alkyl group having from 3 to 6 atoms and having a methyl group as a side chain; and m and n each represents 1 or 2, is disclosed.The liquid crystal compound of formula (I) is optically and electrically stable and exhibits fast electro-optical switching in image display.Type: GrantFiled: December 23, 1987Date of Patent: December 12, 1989Assignee: Takasago International CorporationInventors: Shigeru Mitsuhashi, Hitoshi Kondo, Tetsuharu Okazaki, Shinji Endoh, Hiroko Kudo, Akio Yamaguchi, Haruki Tsuruta, Susumu Akutagawa
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Patent number: 4882085Abstract: An optically active lactic acid derivative represented by the following formula (I): ##STR1## wherein R represents a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 1 to 18 carbon atoms; C* represents an asymmetric carbon atom; l is 0 or 1; m is 1 or 2; A represents a group selected from the following groups (a) and (b):(a) hydroxyl group, halogen, benzyloxy group, phenoxy group, toluenesulfonic acid group, acetyloxy group trifluoroacetyloxy group; ##STR2## (wherein R' is an alkyl group or alkoxy group having 4 to 18 carbon atoms, n is 0 or 1, ##STR3## with proviso that when A is selected from the group in the above group (a), l is 1 and m is 1 or 2; and when A is selected from the groups in the above group (b), m=n=1 when l is 0, or m and n are 0, 1 or 2 and m+n is 1 or 2 when l is 1, and ##STR4##Type: GrantFiled: December 28, 1988Date of Patent: November 21, 1989Assignee: Canon Kabushiki KaishaInventors: Kazuo Yoshinaga, Kazuharu Katagiri, Akira Tsuboyama, Hiroyuki Kitayama, Kenji Shinjo, Chieko Hioki
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Patent number: 4871472Abstract: Compounds of the formula I ##STR1## wherein R.sup.1 and R.sup.2 each independently of one another are R, OR, OCOR, COOR or OCOOR,is alkyl with 1 to 15 C atoms, wherein one or more CH.sub.2 groups which are not adjacent and are not linked by O can also be replaced by --O--, --CO--, --O--CO--, --CO--O--, --CH--halogen, --CHCN-- and/or --CH.dbd.CH--,A.sup.1, A.sup.2 and A.sup.3 each independently of one another are 1,4-phenylene or trans-1,4-cyclohexylene,m, n and o are each 0 or 1,m+n+o is 0, 1 or 2,Z.sup.1 and Z.sup.2 each independently of one another are --CH.sub.2 --O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 -- or a single bond andX is F, Cl, Br, I or CN,with the provisos given in claim 1, can be used as components of ferroelectric liquid crystal phases.Type: GrantFiled: October 9, 1987Date of Patent: October 3, 1989Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Joachim Krause, Volker Reiffenrath, Thomas Geelhaar
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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
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Patent number: 4866199Abstract: An optically active ester compound is provided represented by the following general formula: ##STR1## wherein R.sub.1 is a normal alkyl group having from 6 to 18 carbon atoms; m is zero or one, n is zero or one, and m+n is one or two; X is --CO--O-- or --O--CO--; p is 3 to 6; Y is a hydrogen atom or chlorine atom; R.sub.2 is hydrogen or a normal alkyl group having from 1 to 11 carbon atoms but may be a hydrogen atom only when Y is a chlorine atom; and *C represents an asymmetric carbon atom. The ester compound of the present invention is useful as a ferroelectric liquid crystal compound.Type: GrantFiled: March 8, 1988Date of Patent: September 12, 1989Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Toshihiro Shibata, Masaki Kimura, Norio Kurosawa
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Patent number: 4855482Abstract: The present invention provides a novel bis(phenoxymethyl)benzene derivative or bis(naphthoxymethyl)benzene derivative, which improves the stability of image on a heat sensitive recording paper composed of a leuco dye and a developer.Type: GrantFiled: June 26, 1987Date of Patent: August 8, 1989Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Shinichi Katsura, Yoshirou Uchiyama, Satomi Inoue
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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
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Patent number: 4841094Abstract: Organic compounds having functional groups such as aromatic ester, thioester, or carbonate groups are prepared by reacting an organometallic reactant where the metal is gallium, indium, thallium arsenic, antimony, or bismuth, with a suitable second reactant. For example, the ester ##STR1## can be prepared by reacting an organometallic derivative of hydroquinone with p-phenoxybenzoyl chloride.Type: GrantFiled: July 29, 1988Date of Patent: June 20, 1989Assignee: Raychem LimitedInventor: Ian D. H. Towle
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Patent number: 4834905Abstract: Compounds of the formulaR.sup.1 --Q.sup.1 --(CH.sub.2).sub.m --(COO).sub.n --(CH.sub.2).sub.p --Q.sup.2 --R.sup.2whereinR.sup.1 and R.sup.2 are each independently alkyl or alkoxy each of 1-12 C atoms, F, Cl, Br, CN or --Q.sup.3 --R.sup.3, or one of R.sup.1 and R.sup.2 can also be H;Q.sup.1, Q.sup.2 and Q.sup.3 are each independently 1,4-phenylene, 1,4-cyclohexylene, 1,4-bicyclo(2,2,2)-octylene or 1,3-dioxane-2,5-diyl, each of which is unsubstituted or substituted by 1-4 fluorine, chlorine or bromine atoms;R.sup.3 is alkyl or alkoxy each of 1-8 C atoms, H, F, Cl, Br or CN;m is 1, 2, 3, 4, 5 or 6; n is 0 or 1; and p is 0, 1, 2, 3, 4 or 5; the sum of (m+p) being 2, 4 or 6 and the sum of (m+n+p) being at least 3;but with the proviso that Q.sup.3 is unsubstituted 1,4-phenylene or 1,4-phenylene substituted by a fluorine, chlorine or bromine atom, only when n=1 or (m+p)=6 or at least one of R.sup.1 to R.sup.3 is F, Cl or Br or none of R.sup.1 to R.sup.3 is CN or two of the radicals R.sup.1 to R.sup.Type: GrantFiled: October 3, 1986Date of Patent: May 30, 1989Assignees: Merck Patent Gesellschaft mit beschrankter Haftung, The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Rudolf Eidenschink, Joachim Krause, Beatrice M. Andrews, George W. Gray, Neil Carr
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Patent number: 4834907Abstract: Novel chiral smectic liquid crystalline ester compounds having a superior stability and exhibiting a high response rate when used in the form of display elements and chiral smectic mixtures containing at least one of these compounds are provided, which compounds are expressed by the formula ##STR1## wherein n is an integer of 2 to 16; l is 0, 1 or 2; m is 1 or 2 under the condition of l+m.gtoreq.2; X represents methylene group --CH.sub.2 -- or single bond when l is zero, methylene group --CH.sub.2 -- or ether linkage --O-- when l=1 or ether linkage --O-- when l=2; and Y represents R, OR, --COR, --OCOR, --OCOOR or --COOR wherein R throughout represents an alkyl group of 1 to 18 carbon atoms; and asterisk * shows an optically active carbon atom.Type: GrantFiled: January 8, 1987Date of Patent: May 30, 1989Assignee: Chisso CorporationInventors: Hiromichi Inoue, Shinichi Saito, Kazutoshi Miyazawa, Takashi Inukai, Kanetsugu Terashima
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Patent number: 4830470Abstract: Compounds of the formula ##STR1## wherein m represents is the number 0 or 1; A is a single covalent bond, --CH.sub.2 --CH.sub.2 --, --OCH.sub.2 --, --COO-- or --OOC--; rings B, C and D are 1,4-phenylene optionally substituted with cyano, halogen or lower alkyl; Y.sup.1 and Y.sup.2 are hydrogen or one of them also is cyano; and R.sup.1 and R.sup.2 each represents C.sub.1 -C.sub.18 -alkyl or C.sub.2 -C.sub.18 alkenyl, either of which is optionally halogen-substituted, in which one CH.sub.2 group or two non-adjacent CH.sub.2 groups is/are optionally replaced by oxygen; with the provisos that at least one of R.sup.1 and R.sup.2 has a chiral carbon atom or a C--C double bond or both when A is --COO-- and at least one of R.sup.1 and R.sup.2 has a C--C double bond when A is a single covalent bond, their preparation, liquid crystalline mixtures containing these compounds and their use for electro-optical purposes are described.Type: GrantFiled: May 20, 1987Date of Patent: May 16, 1989Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Hans-Jurgen Fromm, Stephen Kelly, Martin Schadt
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Patent number: 4828754Abstract: A liquid crystalline compound represented by formula ##STR1## wherein R denotes an alkyl or alkoxy group having 1 to 20 carbon atoms,m and n are each 0 or 1, provided m and n are not 1 at the same time. ##STR2## X and Y each denote a hydrogen atom, a halogen atom or a nitro group, provided X and Y are not hydrogen atoms at the same time, and Q* denotes an optically active group having an asymmetric carbon atom and a linear or cyclic alkyl or alkenyl group which may be substituted by a halogen atom, or the like.Type: GrantFiled: February 23, 1988Date of Patent: May 9, 1989Assignees: Dainippon Ink & Chemicals, Inc., Kawamura Institute of Chemical Res.Inventors: Sadao Takehara, Toru Fujisawa, Yoshi Arai, Jitsuo Kurokawa
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Patent number: 4822906Abstract: Intermediate compounds of the structural formula ##STR1## wherein R.sup.60 is hydrogen; halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl; or trifluoromethoxy or difluoromethoxy; R.sup.61 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.62 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.61 and R.sup.62 together are C.sub.2 -C.sub.5 alkylene; R.sup.63 C.sub.1 -C.sub.4 alkyl; R.sup.64 is C.sub.1 -C.sub.4 alkyl; or R.sup.63 R.sup.64 together are C.sub.2 -C.sub.5 alkylene; R.sup.65 and R.sup.66 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.Type: GrantFiled: December 4, 1987Date of Patent: April 18, 1989Assignee: Stauffer Chemical CompanyInventor: Charles G. Carter
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Patent number: 4816179Abstract: A novel liquid crystal compound suitable to use as a component of liquid crystal dielectrics and a liquid crystal composition containing the same are provided, which compound is a dihalogeno-aromatic compound expressed by the formula ##STR1## wherein R is alkyl or alkoxy of 1.about.12 C or alkoxymethyl of 2.about.Type: GrantFiled: January 20, 1987Date of Patent: March 28, 1989Assignee: Chisso CorporationInventors: Shigeru Sugimori, Yasuyuki Goto, Tetsuya Ogawa
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Patent number: 4816604Abstract: The compounds of formula I, ##STR1## where the substituents have various significances, and physiologically acceptable hydrolyzable derivatives thereof having the hydroxy group in the 2 position of the 3-aminopropoxy side chain in esterifield form, are useful as cardioselective .beta.-adrenoceptor blocking agents.Type: GrantFiled: March 9, 1987Date of Patent: March 28, 1989Assignee: William J. LouisInventors: William J. Louis, Richard Berthold, Andre Stoll
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Patent number: 4812259Abstract: An optically active lactic acid derivative represented by the following formula (Ia) or (Ib): ##STR1## wherein R is a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 1-16 carbon atoms, R.sup.1 is an alkyl group having 4-16 carbon atoms, m and n are respectively 1 or 2, k is 0 or 1, and C* is an asymmetric carbon atom. A liquid crystal composition containing the lactic acid derivative and a liquid crystal device using the liquid crystal composition are also disclosed.Type: GrantFiled: October 23, 1986Date of Patent: March 14, 1989Assignee: Canon Kabushiki KaishaInventors: Kazuo Yoshinaga, Kazuharu Katagiri, Kenji Shinjo
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Patent number: 4808338Abstract: Intermediate compounds of the formula ##STR1## wherein X is oxy, thio, sulfinyl or sulfonyl; R is halogen; C.sub.1 C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy; difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl; trifluoromethyl or difluoromethyl; R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, or phenyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene; R.sup.3 hydrogen, C.sub.1 C.sub.4 alkyl, or phenyl with the proviso that R.sup.1 and R.sup.3 are not both phenyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, or phenyl; R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.Type: GrantFiled: February 1, 1988Date of Patent: February 28, 1989Assignee: Stauffer Chemical CompanyInventor: David L. Lee
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Patent number: 4801734Abstract: Nonionic substances which form disk-shaped micelles in aqueous solution and are of the formula ##STR1## where R is H or ##STR2## R.sup.1 is C.sub.1 -C.sub.4 alkyl, R.sup.2 is H or CH.sub.3, x is from 3 to 12 and y is from 3 to 15, and polymers of compounds of the formula I where R is ##STR3## processes for the preparation of the compounds of the formula I and of the polymers, and the use of the compounds described as additives to detergents and cleaning agents, for other surfactant applications and as liquid crystals for optical, electronic and optoelectronic applications.Type: GrantFiled: June 25, 1987Date of Patent: January 31, 1989Assignee: BASF AktiengesellschaftInventors: Hans-Jakob Kock, Ekhard Winkler, Richard Baur, Heino Finkelmann, Markus Schafheutle
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Patent number: 4795579Abstract: 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: February 26, 1987Date of Patent: January 3, 1989Assignee: Commissariat a l'Energie AtomiqueInventors: Claude Vauchier, Francoise Vinet
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Patent number: 4792556Abstract: Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: ##STR1## wherein: R.sup.1 and R.sup.2 are the same and are lower alkoxy or optionally substituted phenoxy,R.sup.3 is lower alkyl, lower alkoxy, or halo and m is 0, 1 or 2 or R.sup.3 is optionally substituted phenyl, optionally substituted phenyl lower alkyl, optionally substituted phenyl lower alkoxy, amino, lower alkylamino, lower dialkylamino, cyano, or S(O).sub.n R wherein R is lower alkyl; optionally substituted phenyl; optionally substituted phenyl lower alkyl; or optionally substituted heterocyclic aryl of three to nine ring atoms containing one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and the pharmaceutically acceptable acid addition salts thereof; and m is 1 and n is 0, 1 or 2;at least one of X or Y is C(O)W and the other X or Y is different and is hydrogen, C(O)W or R.sup.Type: GrantFiled: April 28, 1986Date of Patent: December 20, 1988Assignee: Syntex (U.S.A.) Inc.Inventors: D. V. K. Murthy, Michael C. Venuti, John M. Young
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Patent number: 4784793Abstract: Novel derivatives of cyclic and acyclic terpenoid alcohols, having general formula (I) X--(CO).sub.n --O--T.sub.1, where n=O or l, T.sub.1 is a terpenoid group and X is a combination of cyclic groups, e.g. phenyl, cyclohexyl and pyrimidyl, X preferably contains up to three cyclic groups. Preferred derivatives are esters of cyclic terpenoid alcohols, e.g. menthol, borneol and isopineocampheol, e.g. formula (II) (-)-menthol. Ferroelectric smectic liquid crystal mixtures and devices containing these derivatives as chiral dopants in a tilted smectic host are also described. The properties of various other derivatives of terpenoid alcohols of formula (I) are also described, e.g. those of neomenthol, isolongifolol, fenchol, carveol, myrthenol, nopol, citronellol, perilla alcohol and dihydrocitronellol.Type: GrantFiled: September 22, 1986Date of Patent: November 15, 1988Assignees: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland, STC PLCInventors: David Coates, George W. Gray, David Lacey, Daniel J. S. Young, Kenneth J. Toyne, Matthew F. Bone
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Patent number: 4780542Abstract: The invention relates to the preparation of an ester or an amide from an anhydride with an alcohol or an amine, wherein the anhydride is first prepared by reacting an acid and an alkyl chloroformate in a 100% aqueous medium, that is, 100% water.Type: GrantFiled: September 26, 1983Date of Patent: October 25, 1988Assignee: Montefiore Medical CenterInventor: Iraj Lalezari
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Patent number: 4780550Abstract: Compounds of the formula ##STR1## wherein R is hydrogen; halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.m -- wherein m is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are methyl or ethyl;R.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R hu d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)-- wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) --SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined; and (13) --N(R.sup.c)C(O)R.sup.d wherein R.sup.c and R.sup.Type: GrantFiled: September 17, 1987Date of Patent: October 25, 1988Assignee: Stauffer Chemical CompanyInventor: Charles G. Carter
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Patent number: 4780242Abstract: A novel optically active liquid crystal compound and a liquid crystal composition containing the same are provided, which compound is expressed by the formula ##STR1## wherein R.sub.1 is alkyl or alkoxy of 4-18 C; R.sub.2 is alkyl, alkoxy, acyl or alkoxymethyl of 4-18 C; but either one of R.sub.1 or R.sub.2 is an optically active group; either one of X.sub.1 or X.sub.2 is halogen atom and the other is H; m and n each are 0 or 1 and m+n is 0 or 1.Type: GrantFiled: March 11, 1986Date of Patent: October 25, 1988Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Hiromichi Inoue, Shinichi Saito, Takashi Inukai, Kanetsugu Terashima, Mitsuyoshi Inchihashi
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Patent number: 4778621Abstract: A novel ester compound which, when added to a liqud crystal composition, can raise its nematic phase-isotropic liquid phase transition point without raising its viscosity, and a liquid crystal composition containing the same are provided, which ester compound is expressed by the formula ##STR1## wherein R.sub.1 and R.sub.Type: GrantFiled: October 10, 1986Date of Patent: October 18, 1988Assignee: Chisso CorporationInventors: Toyoshiro Isoyama, Tetsuya Ogawa, Shigeru Sugimori
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Patent number: 4777282Abstract: Organic compounds having functional groups such as aromatic ester, thioester, or carbonate groups are prepared by reacting an organo- germanium, tin, or lead reactant with a suitable second reactant. For example, the ester ##STR1## is prepared by reacting the bis-tri-n-butyl tin derivative of hydroquinone with p-phenoxybenzoyl chloride.Type: GrantFiled: June 3, 1986Date of Patent: October 11, 1988Assignee: Raychem LimitedInventor: Ian D. H. Towle
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Patent number: 4769176Abstract: Biphenyl esters of formula (I), wherein formula (II) represents formula (III) or formula (IV), R.sub.1 represents C.sub.3 -C.sub.12 alkyl, alkoxy, alkylcarbonyloxy, alkoxycarbonyl or alkoxycarbonyloxy, j is 0 or 1, R.sub.2 represents C.sub.3 -C.sub.12 alkyl or alkoxy, one of Q.sub.1 or Q.sub.2 is fluorine and the other is hydrogen, provided that when j is 0 and formula (II) is formula (III) and both R.sub.1 and R.sub.2 are n-alkyl, then the total number of carbon atoms in R.sub.1 and R.sub.2 is more than 12. These compounds may be used as constituents of liquid crystal mixtures which show a room temperature ferroelectric smectic phase, and a number of such mixtures are described.Type: GrantFiled: October 30, 1986Date of Patent: September 6, 1988Assignee: The Secretary of State for Defence In Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Madeline J. Bradshaw, Edward P. Raynes, David I. Bishop, Ian C. Sage, John A. Jenner
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Patent number: 4764619Abstract: An optically active compound having the formula: ##STR1## wherein each of Z and Z' is a single bond, --COO--, --OCO--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 -- or --CH.sub.2 O--, R is an alkyl group having from 1 to 12 carbon atoms, an alkoxyl group having from 1 to 12 carbon atoms, a cyano group or a halogen atom, each of rings A and B is a 1,4-di-substituted phenylene group or a trans-1,4-di-substituted cyclohexylene group, n is 0 or 1, X is ##STR2## wherein * indicates an optical center, and R' is an alkyl group having from 2 to 12 carbon atoms or ##STR3## where R" is a hydrogen atom, an alkyl or alkoxy group having from 1 to 12 carbon atoms, provided that when X is ##STR4## R is the alkyl group or the alkoxy group.Type: GrantFiled: March 21, 1986Date of Patent: August 16, 1988Assignee: Asahi Glass Company Ltd.Inventors: Tomoki Gunjima, Ryutaro Takei, Eriko Aoyama
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Patent number: 4746350Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: Y is selected from phenyl, furyl, thienyl and pyrrolyl rings (each optionally substituted by group X), optionally branched alkylene or alkylenethio(oxy)alkylene;X which may be the same or different are independently selected from halogen, nitro, alkyl, substituted alkyl, hydroxy, alkoxy, carboxy, alkoxycarbonyl, alkylthio, sulfamoyl, substituted sulfamoyl, amino, substituted amino and alkanoyl;R.sup.1 is selected from hydrogen, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl and alkynyl;R.sup.3 is selected from alkyl; andR.sup.4 is selected from hydrogen, alkyl, and alkoxycarbonyl.Type: GrantFiled: April 14, 1986Date of Patent: May 24, 1988Assignee: Imperial Chemical Industries PLCInventor: Keith G. Watson
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Patent number: 4744918Abstract: Liquid crystal phases containing at least one optically active compound of the formula IR.sup.1 --X.sup.1 --CHR.sup.o (CH.sub.2).sub.p X.sup.2 --R.sup.2 Iwherein X.sup.1 and X.sup.2 independently of one another are each --CO--O-- or --O--CO--, one of X.sup.1 and X.sup.2 may also be --O--, R.sup.1 and R.sup.2 independently of one another are each a group --(A.sup.1 --Z).sub.m --(A.sup.2).sub.n -Y, whereinA.sup.1 and A.sup.2 in each case independently of one another are a 1,4-phenylene, pyrimidine-2,5-diyl, pyrazine-2,5-diyl, pyridine-2,5-diyl, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-dithiane-2,5-diyl or 1,4-bicyclo(2,2,2)-octylene group, it also being possible for this to be monosubstituted or polysubstituted by F, Cl, Br, CN and/or alkyl groups with up to 12 C atoms, and it being possible for 1 or 2 non-adjacent CH.sub.2 groups in the alkyl groups to be replaced by O atoms,Z is --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --CH.dbd.N--, --N.dbd.CH--, --N.dbd.N--, --N(O).Type: GrantFiled: July 11, 1985Date of Patent: May 17, 1988Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Gerd Heppke, Feodor Oestreicher
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Patent number: 4737313Abstract: Novel ferroelectric liquid crystals exhibiting a chiral smectic C phase and liquid crystal compositions containing the same are provided, which liquid crystals are substituted biphenyl esters expressed by the general formula ##STR1## wherein R.sub.1 * represents an optically active alkyl group of 4 to 18 carbon atoms; ##STR2## represents ##STR3## or ##STR4## Z represents R.sub.2, R.sub.2 CO or R.sub.2 COO wherein R.sub.2 represents an alkyl group or an alkoxy group each of 1 to 18 carbon atoms; and X and Y each represent hydrogen atom (H), bromine atom (Br), chlorine atom (Cl), fluorine atom (F) or cyano group (CN), and either one of X or Y is always hydrogen atom.Type: GrantFiled: August 8, 1986Date of Patent: April 12, 1988Assignee: Chisso CorporationInventors: Shinichi Saito, Hiromichi Inoue, Kanetsugu Terashima, Takashi Inukai, Kenji Furukawa
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Patent number: 4729847Abstract: A novel, superior, optically active liquid crystal compound exhibiting a smectic C* phase, and a liquid crystal composition containing the same are provided, which compound is expressed by the formula ##STR1## wherein X represents --CH.sub.2 O-- or --OCH.sub.2 --; Y represents --COO-- or --OCO--; and either one of R.sup.1 or R.sup.2 represents an optically active alkyl group, alkoxy group or alkoxycarbonyl group and the other represents a non-optically-active alkyl group or alkoxy group each of 4 to 18 carbon atoms.Type: GrantFiled: July 10, 1986Date of Patent: March 8, 1988Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Hiromichi Inoue, Takashi Inukai, Kanetsugu Terashima
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Patent number: 4728458Abstract: Polyphenyl-based liquid crystal compounds represented by the following general formula (1) and liquid crystal composition containing the same: ##STR1## wherein R.sup.1 represents a straight or branched C.sub.1-18 alkyl group, haloalkyl group, aralkyl group or haloaralkyl group with or without optically active carbon, R.sup.2 represents a straight or branched C.sub.1-6 alkyl group, haloalkyl group or aralkyl group with or without optically active carbon, W represents (1) --OCO-- or --COO--, in which case T represents a halogen atom or a methyl group, or (2) a single bond, --O-- or --OCOO--, in which case T represents a halogen atom, X represents --OCO--, --COO--, --C.tbd.C--, --CH.dbd.N--, --N.dbd.CH, Y represents single bond, --O--, --COO--, --OCO--, --CH.sub.2 --, --OCH.sub.2 --, --COOCH.sub.2 -- or --OCOCH.sub.2 --, Z.sub.1 and Z.sub.2 represent a hydrogen or halogen atom, a cyano group or nitro group, Z.sub.1 may be the same or different from Z.sub.Type: GrantFiled: February 10, 1986Date of Patent: March 1, 1988Assignee: Ajinomoto Co., Ltd.Inventors: Ryoichi Higuchi, Takao Sakurai, Tatsuru Tabohashi, Naoko Mikami, Kiriko Akaiwa, Eri Yamamoto, Koji Takeuchi
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Patent number: 4723005Abstract: 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: GrantFiled: September 10, 1984Date of Patent: February 2, 1988Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Tuong Huynh-Ba, Maged A. Osman
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Patent number: 4717418Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein R.sup.1 is selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, acyl, alkylsulfonyl, benzenesulfonyl, substituted benzenesulfonyl, and an inorganic or organic cation;R.sup.2 is selected from alkyl, alkenyl, alkynyl, substituted alkyl, haloalkenyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl and phenyl; andn is an integer chosen from 2 to 5.The compounds are cereal selective herbicides and in further embodiments of the invention provides processes for the preparation of compounds of formula I, intermediates useful in the preparation of compounds of formula I, herbicidal compositions containing as active ingredient a compound of formula I, and processes for severely damaging or killing unwanted plants by applying to the plants or to the growth medium of the plants an effective amount of a compound of formula I.Type: GrantFiled: November 10, 1982Date of Patent: January 5, 1988Assignee: ICI Australia LimitedInventors: Richard B. Warner, Alexander Serban, Keith G. Watson, Graham J. Bird, Lindsay E. Cross, Graeme J. Farquharson
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Patent number: 4708441Abstract: Compounds of the formula ##STR1## wherein X.sup.2 is a single covalent bond or --COO--; X.sup.1 is a single covalent bond, --COO--, --CH.sub.2 CH.sub.2 -- or when X.sup.2 is --COO--, X.sup.1 also can be p--C.sub.6 H.sub.4 --, p--C.sub.6 H.sub.4 --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --p--C.sub.6 H.sub.4, p--C.sub.6 H.sub.4 --COO-- or --COO--p--C.sub.6 H.sub.4 ; ring A is a benzene ring or trans-1,4-cyclohexylene; ring B is a benzene ring or when X.sup.2 is --COO-- and X.sup.1 is a single covalent bond, --COO-- or --CH.sub.2 CH.sub.2 --, ring B also can be trans-1,4-cyclohexylene; Z.sup.1, Z.sup.2 and Z.sup.3 individually are hydrogen or when positioned on a benzene ring which is not linked directly with a further ring via a single covalent bond, Z.sup.1, Z.sup.2 and Z.sup.3 also can be halogen, cyano or methyl; Y.sup.2 is cyano, nitro, 2,2-dicyanovinyl or when Y.sup.1 is hydrogen Y.sup.2 also can be 2,2-dicyano-1-methylvinyl; Y.sup.1 is halogen, cyano, C.sub.1 -C.sub.3 -alkyl or, when X.sup.Type: GrantFiled: August 16, 1985Date of Patent: November 24, 1987Assignee: Hoffman-La Roche Inc.Inventors: Martin Petrzilka, Martin Schadt, Alois Villiger
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Patent number: 4709030Abstract: Liquid crystalline mixtures containing compounds of the formula ##STR1## wherein n stands for the number 0 or 1; X.sup.1 and X.sup.2 denote single covalent bonds or one of the symbols X.sup.1 and X.sup.2 also denotes --COO--, --OOC-- or --CH.sub.2 CH.sub.2 --; the rings A.sup.1, A.sup.2 and A.sup.3 represent 1,4-phenylene, 2-fluoro-1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also represents a 2,5-disubstituted pyrimidine ring or a trans-2,5-disubstituted m-dioxane ring; R.sup.1 signifies 4-alkenyl or on a cyclohexyl ring also 2Z-alkenyl; and R.sup.2 denotes alkyl, alkoxy, --CN or --NCS,as well as the manufacture of these compounds and the use for electro-optical purposes are described.Type: GrantFiled: July 11, 1986Date of Patent: November 24, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Martin Petrzilka, Martin Schadt
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Patent number: 4701547Abstract: New liquid-crystalline ester compounds which exhibit a liquid-crystalline phase within a broad temperature range and have a positive, dielectric anisotropy, and a liquid-crystalline composition comprising the same are provided which ester compounds are expressed by the general formula ##STR1## wherein R represents hydrogen atom or an alkyl group of 1 to 10 carbon atoms; ##STR2## each represent ##STR3## X represents ##STR4## Y represents hydrogen atom, F, Cl or CN; and Z represents F, Cl or CN.Type: GrantFiled: December 19, 1984Date of Patent: October 20, 1987Assignee: Chisso CorporationInventors: Shigeru Sugimori, Tetsuhiko Kojima
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Patent number: 4689176Abstract: A novel optically active compound suitable for use in a display mode utilizing a ferroelectric liquid crystal, and a chiral smectic liquid crystal composition containing the same are provided, which novel optically active compound is expressed by the formula ##STR1## wherein R represents an alkyl group of 2 to 15 carbon atoms; X represents CN group or a halogen atom; Y and Z each represent a halogen atom or hydrogen atom, but either one of Y and Z is hydrogen atom; l is 1 or 2; m is 0 or 1; and a symbol * shows that the carbon atom having this symbol attached thereto constitutes an optically active center.Type: GrantFiled: December 20, 1985Date of Patent: August 25, 1987Assignee: Chisso CorporationInventors: Hiromichi Inoue, Shinichi Saito, Kazutoshi Miyazawa, Takashi Inukai, Kanetsugu Terashima
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Patent number: 4686289Abstract: 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: GrantFiled: February 25, 1986Date of Patent: August 11, 1987Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Tuong Huynh-Ba, Maged A. Osman
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Patent number: 4683079Abstract: Liquid crystal 4-n-pentylphenyl esters of 4'-(trans-4"-n-alkylcyclohex-2-enoyloxy(benzoic acids of the general formula: ##STR1## wherein R is C.sub.2 H.sub.5, n--C.sub.3 H.sub.7.Type: GrantFiled: June 20, 1986Date of Patent: July 28, 1987Inventors: Vladimir S. Bezborodov, Viktor A. Konovalov, Jury L. Ptashnikov, Vladimir M. Astafiev, Alexandr E. Petrovich
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Patent number: 4683078Abstract: A novel liquid crystal compound suitable to use as a component of liquid crystal dielectrics and a liquid crystal composition containing the same are provided, which compound is a dihalogeno-aromatic compound expressed by the formula ##STR1## wherein R represents an alkyl group or an alkoxy group, each of 1 to 12 carbon atoms, or an alkoxymethyl group of 2 to 12 carbon atoms.Type: GrantFiled: March 4, 1986Date of Patent: July 28, 1987Assignee: Chisso CorporationInventors: Shigeru Sugimori, Yasuyuki Goto, Tetsuya Ogawa
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Patent number: 4676925Abstract: Chiral smectic compounds having a high response rate and being superior as a ferroelectric liquid crystalline material, and chiral smectic mixtures containing the same are provided, which compounds being expressed by the formula ##STR1## wherein X represents --CH.sub.2 --, --O-- or --CO--; n represents 0, 1 or 2; when X represents --CH.sub.2 --, Y represents R--, R--CO--, ROCO--, ##STR2## wherein R represents an alkyl group having 1 to 18 carbon atoms, and when X represents --O-- or --CO--, Y represents R; and * represents a symbol indicating an optically active carbon atom.Type: GrantFiled: April 21, 1986Date of Patent: June 30, 1987Assignee: Chisso CorporationInventors: Hiromichi Inoue, Shinichi Saito, Kanetsugu Terashima, Takashi Inukai, Kenji Furukawa
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Patent number: 4676604Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is hydrogen or straight-chain alkyl; R.sup.2 is --CN, --R, --COR, --COOR or when R.sup.2 is positioned on an aromatic ring R.sup.2 also can be --OR, --OOCR or --F; R is alkyl; A is a group with 1 to 4 six-membered rings, these rings being linked directly with one another and with ring B in each case via a single covalent bond or being linked at one or two positions also via --COO--, --OOC-- or --CH.sub.2 CH.sub.Type: GrantFiled: March 5, 1984Date of Patent: June 30, 1987Assignee: Hoffmann-La Roche Inc.Inventor: Martin Petrzilka
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Patent number: 4672076Abstract: A non-steroidal anti-inflammatory composition comprising an active anti-inflammatory agent having the formula: ##STR1## wherein R.sub.1 and R.sub.2 are hydrogen hydroxy. The active agent is formulated with a pharmaceutically acceptable carrier for use in the treatment of pain, inflammation and other related symptoms on mammals. Benzyl paraben, benzyl salicylate and benzyl benzoate are preferred.Type: GrantFiled: April 27, 1984Date of Patent: June 9, 1987Assignee: Warner-Lambert CompanyInventors: Eugene P. Pittz, Richard V. Smerbeck
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Patent number: 4666510Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: X is selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, substituted alkoxy, alkenyl, alkynyl, alkenyloxy, alkynyloxy, acyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, amino, substituted amino, and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof;R.sup.1 is selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, alkylsulfonyl, arylsulfonyl, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl;m is an integer chosen from 3 to 5.Type: GrantFiled: January 25, 1983Date of Patent: May 19, 1987Assignee: ICI Australia LimitedInventors: Keith G. Watson, Lynette A. Garson, Graham J. Bird, Lindsay E. Cross, Graeme J. Farquharson
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Patent number: 4664851Abstract: Process for the co-production of carboxylic acids of the general formula R.sup.1 --COOH and R.sup.2 --COOH and carboxylic acid esters of the general formula R.sup.1 --COOCH.sub.2 R.sup.2 and R.sup.2 --COOCH.sub.2 R.sup.1 from carboxylic acid esters of the general formula R.sup.1 --COOR.sup.2 and/or ethers of the general formula R.sup.3 OR.sup.4 (R.sup.1, R.sup.2, R.sup.3, R.sup.4 representing (substituted) alkyl or (substituted) aryl, alkaryl or aralkyl, R.sup.1 also representing H), carbon monoxide and hydrogen at elevated temperature and pressure in the presence of a ruthenium compound, a further Group VIII metal compound, and a compound R.sup.5 Hal or R.sup.5 COHal where R.sup.5 has one of the meanings given for R.sup.2 and Hal is iodine or bromine, the reaction mixture being substantially free from other transistion metal or Group II metal iodides or bromides, and containing a trivalent nitrogen compound containing a group ##STR1## (X=O or S), such as an amide, a carbamate, a urea or a derivative thereof.Type: GrantFiled: July 19, 1982Date of Patent: May 12, 1987Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4659372Abstract: 2-Aryl-1,3-cyclohexanedione enol ester compounds exhibit outstanding miticidal, mite ovicidal and herbicidal activity.Type: GrantFiled: November 28, 1983Date of Patent: April 21, 1987Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4659855Abstract: Certain novel aryl sulfonyl fluorides, their preparation, and their use in inhibiting serine proteases with chymotrypsin-like and elastase-like specificity.Type: GrantFiled: May 9, 1983Date of Patent: April 21, 1987Assignee: Georgia Tech Research CorporationInventor: James C. Powers