Esterified Phenolic Hydroxy Patents (Class 560/109)
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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: 5338484Abstract: Disclosed are novel active benzene derivatives represented by the general formula (I): ##STR1## (wherein X represents --COO--, --OCO--, --CH.sub.2 O-- or --OCH.sub.2 --; A represents a hydrogen atom, a halogen atom or an alkyl or alkoxyl group having 1 to 20 carbon atoms: R represents an alkyl group having 1 to 20 carbon atoms; l and m each represents a number of 1 or 2, n represents a number of 0 or 1, but when n is 0 the sum of l and m is 3 or less; and * indicates asymmetric carbon atom), a process for producing the same, liquid-crystalline substances containing said derivatives as active ingredient, and optical switching elements utilizing the liquid crystal compositions containing said liquid-crystalline substances.Type: GrantFiled: October 18, 1993Date of Patent: August 16, 1994Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Higashii, Masayoshi Minai
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Patent number: 5332856Abstract: 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: December 16, 1992Date of Patent: July 26, 1994Assignee: Centre International de Recherches Dermatologiques Galderma (CIRD Galderma)Inventors: Braham Shroot, Jean-Michel Bernardon, William R. Pilgrim
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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
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Patent number: 5306837Abstract: Novel intermediates useful in the preparation of the optically active antiviral compound [1R-(1.alpha.,2.beta.,3.alpha.)]-2-amino-9-[2,3-bis(hydroxymethyl)cyclobut yl]-1,9-dihydro-6H-purin-6-one are described.Type: GrantFiled: July 15, 1993Date of Patent: April 26, 1994Assignee: E. R. Squibb & Sons, Inc.Inventors: Gregory S. Bisacchi, Toomas Mitt
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Patent number: 5274172Abstract: There is disclosed a process for preparing granular esters in one step by the reaction of an alcohol with acid chloride in an aqueous alkaline medium with moderate shear agitation and optionally in the presence of a surfactant.Type: GrantFiled: June 24, 1992Date of Patent: December 28, 1993Assignee: Monsanto CompanyInventors: Yueting Chou, David A. Martin
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Patent number: 5238602Abstract: Compounds of the formula ##STR1## wherein n stands for the number 0 or 1; 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; X.sup.1 represents a single covalent bond, --COO--, --OOC--, --CH.sub.2 CH.sub.2 --, p--C.sub.6 H.sub.4 --, --CH.sub.2 CH.sub.2 --p-- C.sub.6 H.sub.4 --, --CH.sub.2 CH.sub.2 --p--C.sub.6 H.sub.4 --CH.sub.2 CH.sub.2 -- or, insofar as the rings A.sup.1 and A.sup.2 represent 1,4-phenylene, also --NON--; R.sup.2 represents 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or alkenyloxy, with the proviso that the oxygen atom in alkenyloxy is linked with a saturated carbon atom; and R.sup.1 signifies 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or, insofar as R.sup.2 represents alkenyloxy, also alkyl, their manufacture, as well as liquid crystalline mixtures and the use for electro-optical purposes.Type: GrantFiled: May 26, 1987Date of Patent: August 24, 1993Assignee: Hoffmann La Roche Inc.Inventors: Martin Petrzilka, Martin Schadt
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Patent number: 5234946Abstract: The substituted alkylamine derivatives represented by formula (I) ##STR1## wherein R.sup.1 represents (a) substituted or unsubstituted C.sub.2-6 alkenyl group, (b) substituted or unsubstituted C.sub.3-6 cycloalkenyl group, (c) substituted or unsubstituted C.sub.2-6 alkynyl group, (d) substituted or unsubstituted aryl group, (e) substituted or unsubstituted heterocyclic group, (f) fused heterocyclic group which may be substituted, or (g) group represented by the formula Ru.sup.11 -Ar wherein R.sup.11 is a heterocyclic group and Ar is a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and which may be substituted; ##STR2## represents a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and may be substituted by R.sup.7,X and Y are linking groups,R.sup.2 is H or lower alkyl,R.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl or lower cycloalkyl,R.sup.4 and R.sup.5 are independently hydrogen or halogen atoms,R.sup.Type: GrantFiled: August 30, 1991Date of Patent: August 10, 1993Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Hiroshi Takezawa, Masahiro Hayashi, Yoshikazu Iwasawa, Masaaki Hosoi, Yoshiaki Iida, Yoshimi Tsuchiya, Masahiro Horie, Toshio Kamei
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Patent number: 5230830Type: GrantFiled: April 15, 1992Date of Patent: July 27, 1993Assignee: The Secrteary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: David Coates, Simon Greenfield, Ian C. Sage
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Patent number: 5204454Abstract: Prepolymer polyols containing mesogenic moieties useful as reactants for the preparation of resinous materials are disclosed. Synthesized by condensing a polyether polyol with bifunctional mesogenic diacids, or diesters, the compounds of the invention are characterized by their reasonably low melt temperature which renders them suitable as additive materials in polymeric molding compositions and as precursors for the preparation of resinous materials.The liquid crystalline properties of the prepolymers of the invention were found to depend on the type and molecular weight of the glycols and on the molar ratio between the glycols and the mesogenic reactant.Type: GrantFiled: July 19, 1991Date of Patent: April 20, 1993Assignee: Miles Inc.Inventors: Randall A. Rodenhouse, Dittmar K. Nerger, Douglas A. Wicks
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Patent number: 5200550Abstract: 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 monoor 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: July 17, 1990Date of Patent: April 6, 1993Assignee: Centre International de Recherces Dermatologiques Galderma (Cird Galderma)Inventors: Braham Shroot, Jean-Michel Bernardon
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Patent number: 5167863Abstract: There are disclosed an optically active compound represented by the general formula: ##STR1## wherein n, 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 detailed explanation, and *-marked carbon atoms are each an asymmetric carbon atom; a liquid crystal composition comprising at least one optically active compound of said general formula and a liquid crystal optical modulator using the composition thereof.Type: GrantFiled: July 16, 1990Date of Patent: December 1, 1992Assignees: Hitachi, Ltd., Takeda Chemical Industries, Ltd.Inventors: Teruo Kitamura, Katsumi Kondo, Akio Mukoh, Koichi Matsumura, Mitsuru Kawada, Yoshihiro Sugihara
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Patent number: 5144059Abstract: The compound of the formula ##STR1## (wherein R, R.sub.1 and R.sub.2 have the meanings given in the description), salts thereof with pharmaceutically acceptable organic or inorganic acids, process and intermediates for the preparation thereof and a pharmaceutical composition containing said compound are described.The compounds of formula I and the salts thereof are useful in the treatment of heart and renal diseases.Type: GrantFiled: April 20, 1990Date of Patent: September 1, 1992Assignee: Simes Societa Italiana Medicinali E. Sintetici S.A.Inventors: Cesare Casagrande, Francesco Santangelo
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Patent number: 5137653Abstract: This invention provides a novel alkanoyl ester compound represented by general formula (I): ##STR1## (wherein A is of --, --O--, ##STR2## B is ##STR3## l and m are 1 or 2 provided that both are not simultaneously 2, k and n are an integer of 1 or more, respectively, provided that k>n, and R is an alkyl group), a liquid crystal composition containing this compound, a novel alkanoylphenyl compound or a novel alkanoylbiphenyl compound as an intermediate for the production of the above compound, and a method of producing the same. These novel alkanoyl ester compounds are excellent in the stability against light and the like and can take a liquid crystal state at a wide temperature range. Particularly, these compounds form liquid crystals of ferroelectricity having a large spontaneous polarization and a fast response rate by introducing an optically active group into the compound, so that they develop a very excellent effect as a starting material for optoelectronics and its related elements.Type: GrantFiled: October 18, 1991Date of Patent: August 11, 1992Assignee: Nippon Mining Co., Ltd.Inventors: Toshihiro Hirai, Atsushi Yoshizawa, Isa Nishiyama, Mitsuo Fukumasa, Nobuyuki Shiratori, Akihisa Yokoyama
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Patent number: 5133896Abstract: Novel cyanohydrin derivatives of general formula (I) wherein R.sup.1 is hydrogen, alkyl, alkoxy, perfluoroalkyl or perfluoroalkoxy, R.sup.2 is alkyl, r is 1 to 10, n and m are 0 or 1, provided if both n and m are 0 then X is (II) or (III), where (F) indicates one or more optional fluorines, p is 0 or 1, Z is a single bond if p is 0 and COO if p is 1; and if one or both of n or m are 1 then X is (IV), where each ring A, B and C is phenyl, fluoro- or chloro-phenyl, cyclohexyl, pyrimidyl, pyridyl, or dioxanyl, A, B and C are single bonds or linking groups, and (a+b+c) is 2 or 3. Liquid crystal materials containing these compounds are also described.Type: GrantFiled: July 11, 1990Date of Patent: July 28, 1992Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: David Coates, Simon Greenfield, Ian C. Sage
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Patent number: 5130048Abstract: The subject application discloses a chiral nonracemic composition of the general formula:R.sub.1 --Ar--O--CH.sub.2 --C*HX--C*HY--CH.sub.2 --O--R.sub.2wherein R.sub.1 is an achiral tail of two to sixteen carbons; Ar is an achiral FLC core of at least two rings; * denotes a chiral carbon; X and Y are halogens; and R.sub.2 is one to ten carbon atoms. The --O--CH.sub.2 --C*HX--C*HY--CH.sub.2 --O-- segment comprises the chiral proximal segment of the chiral tail; the proximal segment is selected from the enantiomers 2R,3R-dihalo and 2S,3S-dihalo. R.sub.2 is the distal segment of the chiral tail.Type: GrantFiled: July 20, 1990Date of Patent: July 14, 1992Assignee: Displaytech, Inc.Inventors: Michael Wand, William N. Thurmes, David Walba
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Patent number: 5124070Abstract: Disclosed are herein optically active ester derivatives represented by the formula (I): ##STR1## (wherein R.sub.1 represents an alkyl group having 3 to 20 carbon atoms; R.sub.2 represents an optically active alkyl or alkoxyalkyl group having 3 to 15 carbon atoms optionally substituted by halogen atoms; Y represents --O--, --COO-- or --OCO--; X represents --COO-- or --OCO--; l represents a number of 1 or 2; k and m each represents a number of 0 or 1; n represents a number of 1 to 6), preparation processes therefor, liquid crystal materials containing such ester derivatives as active ingredient, and a light switching element using said liquid crystal materials as liquid crystal element.Type: GrantFiled: August 28, 1989Date of Patent: June 23, 1992Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Higashii, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Takeshi Tani, Chizu Kawakami, Koichi Fujisawa, Kiyoshi Imamura
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Patent number: 5120368Abstract: This invention provides novel vanillyl 5-hydroxyesters, and smoking compositions which contain a vanillyl 5-hydroxyester as a flavorant-release additive.Under cigarette smoking conditions, a combustible filler and/or paper wrapper additive such as 4'-formyl-2'-methoxyphenyl 5-hydroxy-2-isopropylhexanoate pyrolyzes into vanillin and 2-isopropyl-5-hydroxyhexanoic acid delta lactone flavorants as volatile components of the cigarette smoke.Type: GrantFiled: August 10, 1990Date of Patent: June 9, 1992Assignees: Philip Morris Incorporated, Philip Morris Products, Inc.Inventors: Yoram Houminer, Kenneth F. Podraza, Everett W. Southwick
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Patent number: 5118683Abstract: Compounds of the formula I ##STR1## wherein R.sup.5 represents C.sub.1 to C.sub.6 -alkyl or the group --(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m --Ar;Z represents O, S or --CH.sub.2 --;n represents an integer of 1 to 8;m represents zero or an integer of 1 to 8;one of R.sup.1 and R.sup.2 represents the group ##STR2## and the other represents hydrogen or R.sup.7 CO--; R.sup.7 is C.sub.1 to C.sub.10 alkyl, C.sub.3 to C.sub.8 cycloalkyl, aryl, heteroaryl, --N(R.sup.9 R.sup.10), or R.sup.11 O--; R.sup.3, R.sup.4, R.sup.9, and R.sup.10 are each independently selected from hydrogen, C.sub.1 to C.sub.6 alkyl and Ar.sup.1 ; R.sup.6 and R.sup.11 are each independently C.sub.1 -C.sub.8 alkyl; Ar and Ar.sup.1 are each independently selected from the group consisting of phenyl or phenyl substituted by one or two substituents selected from the group consisting of R.sup.12, R.sup.13 O--; R.sup.14 S(O).sub.x --, R.sup.15 CO--, (R.sup.16 R.sup.17)NCO--, F, Cl, Br, I, NO.sub.2, CF.sub.3, CN, or phenyl; R.sup.12, R.sup.13, R.sup.Type: GrantFiled: June 13, 1990Date of Patent: June 2, 1992Assignee: Schering CorporationInventors: David J. Blythin, Ho-Jane Shue
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Patent number: 5116869Abstract: 2-Substituted-2-cyclopentenones represented by the formula (I): ##STR1## wherein A is a hydroxyl group or ##STR2## and B is a hydrogen atom or A and B are bonded together to form one bonding arm;R.sup.1 represents a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms;R.sup.2 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms;R.sup.3 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms; wherein,when R.sup.3 is a single bond bonded to the cyclopentene skeleton, X represents a hydrogen atom, a hydroxyl group or a protected hydroxyl group; andwhen R.sup.3 is a double bond bonded to the pentene skeleton, X represents a bonding arm constituting a part of said double bond; andm and n independently represent 0, 1 or 2.Type: GrantFiled: September 3, 1991Date of Patent: May 26, 1992Assignee: Teijin LimitedInventors: Satoshi Sugiura, Atsuo Hazato, Toru Minoshima, Yoshinori Kato, Yasuko Koshihara, Seizi Kurozumi
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Patent number: 5098602Abstract: This invention provides a novel halogen-containing ester compound represented by the following general formula (I): ##STR1## (wherein R is an alkyl group, A is selected from a single bond, --O--, --COO-- and --CO--, both of X and Y are halogen atoms or either one of X and Y is a halogen atom and the other is a hydrogen atom, each of m and n is 0 or 1, m+n=0 or 1, each of k and l is an integer of 1 or more, provide k<l), a liquid crystal composition and a light switching element each containing the above compound as well as a novel fluorophenol compound represented by the following general formula (II): ##STR2## (wherein each of k and l is an integer of 1 or more, provided k<l) as an intermediate for the synthesis of the above ester compound and a method of producing the same.Type: GrantFiled: May 2, 1989Date of Patent: March 24, 1992Assignee: Nippon Mining Co., Ltd.Inventors: Toshihiro Hirai, Atsushi Yoshizawa, Isa Nishiyama, Mitsuo Fukumasa, Nobuyuki Shiratori, Akihisa Yokoyama
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Patent number: 5089660Abstract: A comonomer composition of an aromatic polycyanate and an aromatic monocyanate substituted at each position ortho to the cyanate group, and a polytriazine copolymer derived therefrom.Type: GrantFiled: January 22, 1988Date of Patent: February 18, 1992Assignee: The Dow Chemical CompanyInventors: Daniel J. Murray, Mitchell G. Dibbs, Philip C. Yang
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Patent number: 5059345Abstract: An optically active compound represented by the general formula (I) of:R--Z--COO--(Ph).sub.k --Ph(Y)--CO--(CH.sub.2).sub.m C*HE L (1)In the general formula (I); R is an alkyl or alkoxy group having 4 to 22 carbon atoms; Z is the one selected from the group consisting of --Ph--, --Ph(X)--, --Ph--Ph--, Ph(X)--Ph--, --Ph--cy--, --Ph(X)--cy-- and --py--Ph-- is a 1,4-substituted phenylene group; --Ph--Ph-- is a 4,4'-substituted diphenylene group; --cy-- is a trans-1,4-cyclohexane group, --py is 2,5-substituted pyrimide group; X is a halogen atom at the ortho-position to R; k is zero or 1, Y is the one selected from the group consisting of H, OH, halogen atoms and methyl group; C* is an asymmetric carbon atom; E is the one selected from the group consisting of methyl group, halogen atoms and CF.sub.3 ; L is an alkyl, aryl or aralkyl group having not more than 10 carbon atoms; and m is an integer of zero to 6 where m takes zero when Y is H and Z is --Ph-- or --Ph--Ph--.Type: GrantFiled: November 3, 1988Date of Patent: October 22, 1991Assignee: Nippon Telegraph and Telephone CorporationInventors: Shogo Kobayashi, Shigeki Ishibashi, Toshio Horie, Shinji Tsuru, Kouzaburou Nakamura, Tohru Maruno
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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
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Patent number: 5051527Abstract: The invention lies in novel ferroelectric liquid crystal compounds particularly represented by the general formulae, having a good responsibility in relation to the applied electric field and a wide range of phase transition points inclusive of the room temperature so as to be useful alone as the liquid crystal material but also to be mixed with other liquid crystal compounds for expanding the phase transition points to a desired range and making the response speed of the liquid crystal composition faster. ##STR1## In the formulae, m and n are same or different with each other and represent an integral of 1-20.Type: GrantFiled: February 28, 1989Date of Patent: September 24, 1991Assignee: Showa Shell Sekiyu K.K.Inventors: Yoshiichi Suzuki, Takashi Hagiwara, Hiroyuki Mogamiya
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Patent number: 5013753Abstract: Compounds of formula ##STR1## (wherein R, R.sub.1, R.sub.2 and X have the meanings reported in the specification), the processes for their preparation and the pharmaceutical compositions containing them as active ingredient are described.The compounds of formula I are useful in the treatment of Parkinson's disease, renal failure, cardiac decompensation and hypertension.Type: GrantFiled: July 28, 1989Date of Patent: May 7, 1991Assignee: SimesInventors: Cesare Casagrande, Francesco Santangelo
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Patent number: 5013479Abstract: Disclosed are herein optically active ether derivatives represented by the formula (I): ##STR1## (wherein X represents --COO-- or --OCO--; A represents an alkyl or alkoxyl group having 3 to 15 carbon atoms; R represents an alkyl or alkyloxyalkyl group having 1 to 20 carbon atoms; l and m each represents a number of 1 to 2; and * indicates an asymmetric carbon atom), preparation processes therefor, liquid crystal materials containing such ether derivatives as active ingredient, and an optical switching element using said liquid crystal materials as liquid crystal element.Type: GrantFiled: April 18, 1990Date of Patent: May 7, 1991Assignees: Sumitomo Chemical Company, Limited, Hitachi, Ltd.Inventors: Masayoshi Minai, Takayuki Higashii
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Patent number: 5002693Abstract: Disclosed are novel active benzene derivatives represented by the general formula (I): ##STR1## (wherein X represents --COO--, --OCO--, --CH.sub.2 O-- or --OCH.sub.2 --; A represents a hydrogen atom, a halogen atom or an alkyl or alkoxyl group having 1 to 20 carbon atoms; R represents an alkyl group having 1 to 20 carbon atoms; l and m each represents a number of 1 or 2, n represents a number of 0 or 1, but when n is 0 the sum of l and m is 3 or less; and * indicates asymmetric carbon atom), a process for producing the same, liquid-crystalline substances containing said derivatives as active ingredient, and optical switching elements utilizing the liquid crystal compositions containing said liquid-crystalline substances.Type: GrantFiled: March 18, 1988Date of Patent: March 26, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Higashii, Masayoshi Minai
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Patent number: 4985180Abstract: Phenyl esters of substituted acids are prepared by a two-step process in which a phenol derivative is first treated with an acid halide to yield a phenyl ester intermediate, and the intermediate is reacted with an appropriate nucleophile.Type: GrantFiled: June 6, 1989Date of Patent: January 15, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventors: Harold E. Bellis, Donald J. Dumas, George C. Sonnichsen, Vinayakam Subramanyam
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Patent number: 4979805Abstract: A ferroelectric liquid crystal composition containing an optically active mesomorphic compound represented by the following formula (I) or (II): ##STR1## wherein R.sub.1 and R.sub.2 are respectively an alkyl, and C with * represents an asymmetric carbon atom. The mesomorphic compound provides the ferroelectric liquid crystal composition with an extended operational life in a liquid crystal device.Type: GrantFiled: December 1, 1989Date of Patent: December 25, 1990Assignee: Canon Kabushiki KaishaInventors: Kazuo Yoshinaga, Kazuharu Katagiri
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Patent number: 4966915Abstract: An L-dopa derivative represented by formula (I) ##STR1## wherein one of R.sup.1 and R.sup.2 denotes a hydrogen atom and the other denotes a group of formula R--CO-- in which R denotes an alkyl, alkenyl, optionally substituted cycloalkyl, optionally substituted phenyl, optionally substituted aralkyl, lower alkoxy or optionally substituted aralkyloxy group,and its acid addition salt. The compounds are useful in the medical field, especially in the treatment of a series of diseases called Parkinson's disease or Parkinsonism.Type: GrantFiled: September 16, 1988Date of Patent: October 30, 1990Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Yoshimi Tsuchiya, Masahiro Hayashi, Hiroshi Takehana, Akihiro Hisaka, Yoshio Sawasaki, Masaki Ihara
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Patent number: 4943384Abstract: Cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 IwhereinR.sup.1 and R.sup.2 are each H or an alkyl group which has 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-groups, and/or --CO--O-- groups and/or --CH.dbd.CH-- groups, or are F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, A.sup.4 --Z.sup.o --A-- or --A--Z.sup.o --A.sup.4 --,A is a trans-1,4-cyclohexylene or 1,4-cyclohexenylene group which is unsubstituted or is monosubstituted or polysubstituted in the 2-, 3-, 5- and/or 6-position by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group each of which has 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups, which trans-1,4-cyclohexylene or 1,4-cyclohexenylene group can optionally also be substituted in the 1-position and/or 4-position and one or two CH.sub.Type: GrantFiled: November 21, 1986Date of Patent: July 24, 1990Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Wolfgang Sucrow, Herbert Wolter, Rudolf Eidenschink
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Patent number: 4908474Abstract: Hitherto processes proposed in recent years for preparing esters of phenol sulphonate salts by reaction between a carboxylic acid chloride and a phenol sulphonate salt place considerable emphasis upon dehydrating the reactants before they are brought into contact in an organic solvent reaction medium.The present invention avoids the problems of employing non-aqueous solvents by carrying out the reaction under aqueous conditions but with controlled alkalinity and water content, especially at a base to phenol sulphonate mole ratio of from 1.3:1 to 1.6:1 and a total water to phenol sulphonate (as the anhydrous material) of not more than 4.5:1. The reaction advantageously employs in preference only a small molar excess of carboxylic acid chloride over the phenol sulphonate and preferably has a reaction temperature controlled to below 30.degree. C., expecially 5.degree. to 20.degree. C.Type: GrantFiled: May 26, 1988Date of Patent: March 13, 1990Assignee: Interox Chemicals LimitedInventors: John P. Sankey, Robert Johnson
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Patent number: 4900476Abstract: An asymmetric synthesis for Vitamin E in an optically active pure form for 4-(2,5-diloweralkanoyloxy)-3,4,6-trimethylphenyl-butan-2-one and intermediates therein.Type: GrantFiled: January 30, 1989Date of Patent: February 13, 1990Assignee: Hoffmann-La Roche Inc.Inventors: Ka-kong Chan, Gabriel G. Saucy
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Patent number: 4897216Abstract: 2,3-Difluorophenol derivatives of the formula ##STR1## wherein R.sup.1 and R.sup.2, in each case independently of one another, are an alkyl group having 1 to 15 C atoms in which, in addition, one or two nonadjacent CH.sub.2 groups may be replaced by --O--, --CO--, --CH.dbd.CH-- and/or --C.tbd.C--;A is 1,4-phenylene which is unsubstituted or substituted by one or two fluorines, or is trans-1,4-cyclohexylene or a single bond; andL.sup.1 and L.sup.2, in each case independently of one another, are H or F,are suitable as components of liquid-crystalline media.Type: GrantFiled: March 9, 1989Date of Patent: January 30, 1990Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Volker Reiffenrath, Joachim Krause, Andreas Wachtler, Georg Weber, Thomas Geelhaar
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Patent number: 4886902Abstract: This invention relates to a novel process for the preparation of isocyanates containing silylated alcoholic or phenolic hydroxyl groups as substituents and to the use of the compounds obtained by this process as reactants for isocyanatocarboxylic acid halides in the preparation of polyisocyanates containing ester groups.Type: GrantFiled: June 20, 1989Date of Patent: December 12, 1989Assignee: Bayer AktiengesellschaftInventors: Werner Mormann, Gabriele Leukel
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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: 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: 4877898Abstract: A process for the one step esterification of aldehydes and alcohols comprises the steps of combining an aldehyde with an alcohol, in the presence of oxygen and in contact with a catalyst having the general formulaPdTe.sub.a Zn.sub.d E.sub.ewhereE is one or more metals from the group consisting of group IA, IIA, IVA, VIIB or VIII metals, As or Sb; anda, d and e are from about 0 to 3 with the proviso that at least d or e.noteq.0.Type: GrantFiled: June 12, 1986Date of Patent: October 31, 1989Assignee: The Standard Oil CompanyInventors: Christos Paparizos, Wilfrid G. Shaw, James L. Callahan
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Patent number: 4876382Abstract: Two kinds of novel fluorobenzophenones represented by the general formula (A), wherein X is F or Cl, are synthesized from 1,2-difluorobenzene and 4,4'-difluorobenzophenone, respectively. Novel fluorophenyl fluorobenzoates represented by the general formula (B), wherein X is F or Cl, are obtained by oxidizing the fluorobenzophenones (A), respectively, in an organic solvent by using trifluoroacetic acid and aqueous solution of hydrogen peroxide. By hydrolysis of each of the fluorobenzoates (B), 3,4-difluorophenol or 3-chloro-4-fluorophenol can easily be obtained.Type: GrantFiled: January 13, 1988Date of Patent: October 24, 1989Assignee: Central Glass Company, LimitedInventors: Yasunobu Nishimura, Toshikazu Kawai
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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: 4867916Abstract: Phenol sulphonate esters can be made in a known process by reacting an alkali metal phenol sulphonate salt with an acyl halide in a hydrocarbon solvent at elevated temperatures, but the use of anhydrous materials were strongly advocated because any residual water hydrolyses the acyl chloride in a competitive reaction. However, it becomes particularly difficult and expensive to dehydrate phenol sulphonate salts below about 2% w/w water on a commercial scale and the product obtained by reaction from such partly dehydrated salts can be comparatively impure or reduced in yield. Consequently, changes to the process such as omitting the solvent or using a different acylating agent have been proposed, but these alternatives introduce their own respective manufacturing problems such as entrainment of viscous acyl chloride and anhydride in the product or introduction of a cumbersome and hence expensive recovery process involving an extra distillation step amongst others.Type: GrantFiled: December 3, 1987Date of Patent: September 19, 1989Assignee: Interox Chemicals LimitedInventors: William R. Sanderson, John P. Sankey
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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: 4855429Abstract: The novel compounds are chiral esters formed from .alpha.-substituted carboxylic acids and mesogenic hydroxyl compounds of the general formula (I) ##STR1## in which the symbols have the following meaning: MO=molecular radical of a mesogenic hydroxyl compound MOH after removing an H, the radial MO being expressed by the general formula (II):R.sup.2 --(A.sup.1).sub.n1 --(B--).sub.n2 (A.sup.2).sub.n3 --O(II)where the meaning ofR.sup.2 is a straight-chain or branched (C.sub.1 -C.sub.12)alkyl or alkenyl, it being possible for one or two nonadjacent CH.sub.2 groups to be replaced by O and/or S atoms, or if n1=1, also F, Cl, Br or CN,A.sup.1, A.sup.2 are, independently of each other, 1,4-phenylene, pyrimidine-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, it being possible for said groups to be substituted at least singly by F, Cl, Br, CN and/or (C.sub.1 -C.sub.12)alkyl (optionally, one or two nonadjacent CH.sub.Type: GrantFiled: May 28, 1987Date of Patent: August 8, 1989Assignee: Hoechst AktiengesellschaftInventors: Gerd Heppke, Christian Bahr, Ingrid Muller, Dieter Ohlendorf, Rainer Wingen
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Patent number: 4841081Abstract: A method of optically resolving a racemate, or a diastereomeric mixture, of a substituted or unsubstituted glycidyl ester or ether compound having at least one glycidylic structure represented by the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3, independently from each other, represent H or CH.sub.3, and 1 to 3 asymmetric carbon atoms in the molecule, or a racemate of a beta-dihalohydrin ester compound, which comprises contacting said racemate or diastereomeric mixture with an optically active form of a compound having the following formula (I) ##STR2## wherein X represents a halogen atom, to form an inclusion complex compound having the optically active compound of formula (I) as a host, and separating the resulting complex compound.Type: GrantFiled: October 14, 1986Date of Patent: June 20, 1989Assignee: Osaka Soda Co., Ltd.Inventors: Fumio Toda, Koichi Tanaka, Tetsuya Nakata
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Patent number: 4831185Abstract: An asymmetric synthesis for Vitamin E in an optically active pure form for 4-(2,5-diloweralkanoyloxy)-3,4,6-trimethylphenyl-butan-2-one and intermediates therein.Type: GrantFiled: December 18, 1987Date of Patent: May 16, 1989Assignee: Hoffmann-La Roche Inc.Inventors: Ka-kong Chan, Gabriel G. Saucy
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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: 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: RE34726Abstract: The subject application discloses a chiral nonracemic composition of the general formula:R.sub.1 --Ar--O--CH.sub.2 --C*HX--C*HY--CH.sub.2 --O--R.sub.2wherein R.sub.1 is an achiral tail of two to sixteen carbons; Ar is an achiral FLC core of at least two rings; * denotes a chiral carbon; X and Y are halogens; and R.sub.2 is one to ten carbon atoms. The --O--CH.sub.2 --C*HX--C*HY--CH.sub.2 --O-- segment comprises the chiral proximal segment of the chiral tail; the proximal segment is selected from the enantiomers 2R,3R-dihalo and 2S,3S-dihalo. R.sub.2 is the distal segment of the chiral tail.Type: GrantFiled: April 29, 1993Date of Patent: September 13, 1994Assignee: Displaytech, Inc.Inventors: Michael Wand, William N. Thurmes, David Walba