Alicyclic Ring And Halogen Containing Patents (Class 568/669)
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Patent number: 12122875Abstract: The present invention relates to a process for the synthesis of partially and fully fluorinated polyether (PFPE) polymers, to PFPE polymers obtained therefrom and to the use of said PFPE polymers as intermediate compounds for the manufacture of additives for plastic and glass coating.Type: GrantFiled: April 18, 2019Date of Patent: October 22, 2024Assignee: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.Inventors: Giovanni Fontana, Marco Galimberti, Vito Tortelli
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Publication number: 20150098903Abstract: One aspect of the present invention relates to compounds, compositions and methods for diagnosis and/or treatment of a subject suffering from an amyloidosis-associated pathological condition. In certain embodiments, the imaging and/or therapeutic agents of the instant invention may be administered to a subject for identification and/or treatment of amyloid deposits. A specific imaging method detects amyloid deposits by administering the imaging agent to the subject and detecting the spatial distribution of the agent. Differential accumulation of the agent is indicative of AD or an amyloidosis-associated pathological condition and can be monitored by using a PET or SPECT camera.Type: ApplicationFiled: December 15, 2014Publication date: April 9, 2015Inventors: David R. Elmaleh, Timothy M. Shoup, Hongning Fu
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Patent number: 8945420Abstract: The invention relates to an electro-optical liquid-crystal display which contains, as dielectric, a liquid-crystalline medium having negative dielectric anisotropy and includes a backlight which essentially only emits light having a wavelength of 400 nm or more or has, between the liquid-crystal layer and the backlight, a cut-off filter which essentially only allows light having a wavelength of 420 nm or more to pass through. In particular, the liquid-crystalline medium comprises a) a (first) dielectrically negative component (component A) which consists of one or more dielectrically negative compounds of the formula I in which the parameters have the meanings indicated in claim 2, and a further (second) dielectrically negative component (component B).Type: GrantFiled: January 17, 2011Date of Patent: February 3, 2015Assignee: Merck Patent GmbHInventors: Atsutaka Manabe, Kazuaki Tarumi, Hubert Spreitzer, Axel Jansen, Melanie Klasen-Memmer
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Publication number: 20130172191Abstract: A method to inhibit the ethylene response in plants with cyclopropene compounds by first generating stable cyclopropane precursor compounds and then converting these compounds to the gaseous cyclopropene antagonist compound by use of a reducing or nucleophilic agent.Type: ApplicationFiled: February 25, 2013Publication date: July 4, 2013Inventors: Richard Martin Jacobson, Martha Jean Kelly, William Nixon James
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Patent number: 8304037Abstract: A liquid crystal compound having general physical properties necessary for a liquid crystal compound, a high stability to heat, light or the like, a small viscosity, a suitable refractive index anisotropy, a suitable dielectric anisotropy and steep electro-optic characteristics, a wide temperature range of a nematic phase and an excellent compatibility with other liquid crystal compounds, and a liquid crystal compound especially having a wide temperature range of a nematic phase. A compound represented by formula (1). with, for example, R1 and R2 are alkyl having 1 to 10 carbons; A1 is 1,4-cyclohexylene; A2 is 2,3-difluoro-1,4-phenylene; X is fluorine or chlorine; Z1 and Z2 are a single bond; and p and q is 0 or 1.Type: GrantFiled: May 24, 2011Date of Patent: November 6, 2012Assignees: JNC Corporation, JNC Petrochemical CorporationInventor: Tomohiro Yano
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Patent number: 8124196Abstract: A liquid crystal composition comprising at least one compound having a fluorobicyclo[2.2.2]octane skeleton represented by formula (I) below is disclosed. A fluorobicyclo[2.2.2]octane compound represented by formula (II) below is also disclosed. In the formulae, Y represents a hydrogen atom or fluorine atom.Type: GrantFiled: March 11, 2010Date of Patent: February 28, 2012Assignee: FUJIFILM CorporationInventors: Takashi Miyahara, Masayuki Harada
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Patent number: 8058481Abstract: Described is a process for the alkoxylation of alcohols with I, Cl, or CH3CO2 endgroups, using alkylene epoxides in the presence of boron based catalysts.Type: GrantFiled: April 30, 2009Date of Patent: November 15, 2011Assignee: E.I. du Pont de Nemours and CompanyInventors: Kenneth Gene Moloy, James A. Schultz
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Publication number: 20110136713Abstract: Hydrofluoro alcohols of formula (I): A—(Rf)a—CFX—O—RhO—(CFX—(Rf)a*—CFX—O—RhO—)nH in which: Rh is a hydrocarbon-based chain; X is F or a C1-C6 (per)fluoroalkyl; a or a* is 0 or 1; Rf is a (per)fluoro(poly)oxyalkylene chain or a (per)fluoroalkyl chain; A is selected from the group consisting of —F, —Cl, and —H (possible only when a=1) or is HO—Rh—O—CFX—; n is an integer from 0 to 200, with the condition that n=0 when A is selected from the group consisting of —F, —Cl, and —H.Type: ApplicationFiled: August 7, 2009Publication date: June 9, 2011Applicant: SOLVAY SOLEXIS S.P.A.Inventors: Giuseppe Marchionni, Ugo De Patto, Marco Avataneo
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Patent number: 7795468Abstract: This invention is directed to functionalized higher diamondoids having at least one functional group. Preferably these derivatives have the following Formula I: wherein D is a higher diamondoid nucleus and wherein R1, R2, R3, R4, R5 and R6 are independently selected from a group consisting of hydrogen and functional groups, provided that there is at least one functional group on the derivative. The functionalized higher diamondoid compounds may also be of the formula D—L—(D)n wherein D is a higher diamondoid nucleus and L is a linking group and n is 1 or more. The functionalized higher diamondoid compounds additionally may be of the formula R38—D—D—R39 wherein D is a higher diamondoid nucleus and R38 and R39 are substituents.Type: GrantFiled: December 6, 2002Date of Patent: September 14, 2010Assignee: Chevron U.S.A. Inc.Inventors: Shenggao Liu, Robert M. Carlson, Jeremy E. Dahl, Waqar R. Qureshi
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Patent number: 7615262Abstract: The present invention provides a liquid crystal material, method for producing the liquid crystal material, and liquid crystal device thereof which shows low light absorption in the ultraviolet light region. A compound of formula (I) wherein R is an alkyl or alkenyl group which is optionally interposed with one or more oxygen or sulphur atoms, Y is independently selected from oxygen or sulphur, n is an integer of from 2 to 8, X is a direct bond, C1-4alkylene or C2-4alkenylene, and A is selected from a various specified ring structures. The liquid crystal material (compounds) are of low birefringence and are U.V. stable and are useful in liquid crystal devices that need low birefringence such as reflective displays, or which are exposed to high levels of U.V. light such as phosphor display cells.Type: GrantFiled: July 15, 2005Date of Patent: November 10, 2009Assignee: Japan Science and Technology AgencyInventors: Neil Campbell, Jun Yamamoto, Hiroshi Yokoyama
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Patent number: 7592407Abstract: A polymerizable fluorinated compound having formula (2a) or (2b) wherein R1 and R2 are H or C1-C20 alkyl or fluoroalkyl, R3 is H, F or C1-C4 alkyl or fluoroalkyl, and R is H or a protective group is polymerized into a fluorinated polymer which is used as a base polymer to formulate a resist composition having transparency to laser light of wavelength?300 nm, alkali development amenability, and dry etch resistance.Type: GrantFiled: October 27, 2005Date of Patent: September 22, 2009Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Yuji Harada, Jun Hatakeyama, Takeru Watanabe, Takeshi Kinsho
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Patent number: 7470499Abstract: A noble alicyclic unsaturated compound represented by the general formula (1): wherein at least one of R1 and R2 is a fluorine atom or a fluorinated alkyl group; a polymer formed by the polymerization of a polymer precursor comprising the alicyclic compound. The polymer is useful, in the lithography using a light having a wavelength of 190 nm or less, as a chemically amplified resist which exhibits excellent transparency with respect to the light for use in exposure and also is excellent in the adhesion to a substrate and the resistance to dry etching.Type: GrantFiled: March 4, 2004Date of Patent: December 30, 2008Assignee: NEC CorporationInventors: Katsumi Maeda, Kaichiro Nakano
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Patent number: 7402712Abstract: Provided by the present invention are an adamantyl vinyl ether compound which is useful as a monomer for functional resins in the photolithography field or a raw material therefor and medical and agricultural intermediates and a production process for the same. The present invention relates to a production process for an adamantyl vinyl ether compound, characterized by subjecting an adamantyl vinyl ether compound having a specific structure and alcohol having an eliminating group in a ? position to chloroalkyl-etherification, then subjecting it to etherification to form an adamantyl group-containing ether and then subjecting it to vinyl-etherification.Type: GrantFiled: June 8, 2004Date of Patent: July 22, 2008Assignee: Idemitsu Petrochemical Co., Ltd.Inventors: Naoyoshi Hatakeyama, Shinji Tanaka, Hidetoshi Ono, Kouichi Kodoi
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Patent number: 7319173Abstract: A process for preparing (per)fluorohalogenethers having general formula: wherein: A and A?, equal to our different from each other, are selected among Cl, Br, H; m=1, 2; n=0, 1; R1 is a fluorinated substituent, preferably perfluorinated, selected from the following groups: C1-C20 linear or branched alkylic; C3-C7 cycloalkylic; aromatic, C6-C10 arylalkyl; heterocyclic or C5-C10-alkylheterocyclic; preferably perfluoroalkyl; R? is as defined in the application; by reaction of carbonyl compounds having formula: wherein: R1 and n are as above; u=0, 1; R? is as defined in the application; in liquid phase, with elemental fluorine and with olefinic compounds of formula: CAF?CA?F2??(III) wherein A and A? are as above, at temperatures from ?120° C. to ?20° C., preferably from ?100° C. to ?40° C., optionally in the presence of an inert solvent under the reaction conditions.Type: GrantFiled: January 28, 2005Date of Patent: January 15, 2008Assignee: Solvay Solexis S.p.A.Inventors: Vito Tortelli, Stefano Millefanti, Pierangelo Calini
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Patent number: 7256316Abstract: A fluorine-containing vinyl ether represented by formula 1, wherein R represents an organic group containing at least one fluorine atom and a cyclic structure is provided. A fluorine-containing copolymer containing (a) a first unit derived from a first monomer that is a fluorine-containing vinyl ether represented by formula 8: where R1 is —H or a C1-C8 alkyl group that optionally contains an oxygen atom; and (b) a second unit derived from a second monomer that is at least one selected from acrylic esters and methacrylic esters is also provided.Type: GrantFiled: October 30, 2003Date of Patent: August 14, 2007Assignee: Central Glass Company, LimitedInventors: Satoru Kobayashi, Kazuhiko Maeda, Tooru Tsujishita
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Patent number: 7172989Abstract: In a process for preparing alcohols by catalytic hydrogenation of carbonyl compounds over a catalyst comprising rhenium on activated carbon, the catalyst used comprises rhenium (calculated as metal) in a weight ratio to the activated carbon of from 0.0001 to 0.5, platinum (calculated as metal) in a weight ratio to the activated carbon of from 0.0001 to 0.5 and, if appropriate, at least one further metal selected from among Zn, Cu, Ag, Au, Ni, Fe, Ru, Mn, Cr, Mo, W and V in a weight ratio to the activated carbon of from 0 to 0.25, and the activated carbon has been nonoxidatively pretreated. It is also possible to prepare ethers and lactones if the hydrogen pressure is not more than 25 bar. In this case, the activated carbon in the catalyst may also have been nonoxidatively pretreated.Type: GrantFiled: April 13, 2005Date of Patent: February 6, 2007Assignee: BASF AktiengesellschaftInventors: Rolf-Hartmuth Fischer, Rolf Pinkos, Stephan Andreas Schunk, Joachim Wulff-Döring, Frank Stein, Thomas Nöbel, Sylvia Huber
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Patent number: 7166731Abstract: There are provided a method of simply preparing a 1,4,6-substituted, 1,4-substituted, 1,6-substituted, or 1-substituted fulvene compound, the intermediates of the fulvene compound, and a method of preparing an ansa-metallocene compound in which two cyclopentadienyl ligands are bridged by one carbon and there are substituents only at positions adjacent to the bridging point of a cyclopentadienyl ligand, using the fulvene compound.Type: GrantFiled: October 13, 2004Date of Patent: January 23, 2007Assignee: LG Chem. Ltd.Inventors: Young Whan Park, Hyosun Lee, Sung Don Hong, Kwang Ho Song, Boong Goon Jeong, Dae Woo Nam, Hye Young Jung, Bun Yeoul Lee, Young Chul Won
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Patent number: 7160967Abstract: Fluorovinyl ethers having the formula CFX?CXOCF2OR, wherein R is a C2–C6 linear, branched or C5–C6 cyclic (per)fluoroalkyl group, or a C2–C6 linear, branched (per)fluoro oxyalkyl group containing from one to three oxygen atoms; when R is fluoroalkyl or fluorooxyalkyl group as above defined, it can contain from 1 to 2 atoms, equal or different, selected from the following: H, Cl, Br, I; X?F, H; and homopolymers or polymers obtainable polymerizing said Fluorovinyl ethers with at least another polymerizable monomer.Type: GrantFiled: April 27, 2005Date of Patent: January 9, 2007Assignee: Solvey Solexis S.p.A.Inventor: Walter Navarrini
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Patent number: 7138550Abstract: Disclosed herein is a fluorinated bridged carbocyclic compound that can be polymerized by itself or with at least one other ethylenically unsaturated monomer to provide a polymer. The polymer may be used, for example, within a sub-300 nm photoresist composition. Also disclosed is a method to make the bridged carbocyclic compound.Type: GrantFiled: February 23, 2004Date of Patent: November 21, 2006Assignee: Air Products and Chemicals, Inc.Inventors: Richard Van Court Carr, Thomas John Markley, Atteye Houssein Abdourazak, John Anthony Marsella
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Patent number: 7109383Abstract: The invention relates to a fluorine-containing allyl ether compound represented by the formula 1, wherein R represents an organic group containing at least one fluorine atom and an alicyclic structure. The invention further relates to a fluorine-containing copolymer containing a first unit derived from the fluorine-containing allyl ether represented by the formula 1; and a second unit derived from a vinyl monomer.Type: GrantFiled: September 26, 2003Date of Patent: September 19, 2006Assignee: Central Glass Company, LimitedInventors: Satoru Kobayashi, Katsunori Kawamura, Kazuhiro Yamanaka, Haruhiko Komoriya, Kazuhiko Maeda
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Patent number: 6858760Abstract: A fluorine-containing cyclic compound is represented by the formula 1: wherein each of R1, R2 and R3 independently represents a hydrogen, alkyl group, fluorine, fluoroalkyl group or hexafluorocarbinol group, wherein at least one of the hexafluorocarbinol groups may partly or totally be protected with a protecting group, and wherein the protecting group is (a) a straight-chain, branched or cyclic hydrocarbon group having a carbon atom number of 1-25 or (b) an aromatic hydrocarbon group and optionally contains a fluorine atom, oxygen atom, nitrogen atom or carbonyl bond.Type: GrantFiled: February 20, 2004Date of Patent: February 22, 2005Assignee: Central Glass Company, LimitedInventors: Haruhiko Komoriya, Satoru Miyazawa, Katsunori Kawamura, Satoru Kobayashi, Kazuhiko Maeda
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Publication number: 20040116750Abstract: The invention relates to a fluorine-containing allyl ether compound represented by the formula 1, 1Type: ApplicationFiled: September 26, 2003Publication date: June 17, 2004Applicant: Central Glass Company, LimitedInventors: Satoru Kobayashi, Katsunori Kawamura, Kazuhiro Yamanaka, Haruhiko Komoriya, Kazuhiko Maeda
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Patent number: 6653512Abstract: Described are compositions comprising perfluoroalkyl haloalkyl ethers and, optionally, surfactant; uses for perfluoroalkyl haloalkyl ether compounds and compositions thereof, optionally comprising surfactant; and perfluoroalkyl haloalkyl ethers.Type: GrantFiled: January 14, 1999Date of Patent: November 25, 2003Assignee: 3M Innovative Properties CompanyInventors: Frederick E. Behr, Richard M. Flynn
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Publication number: 20030199710Abstract: This invention is directed to functionalized higher diamondoids having at least one functional group.Type: ApplicationFiled: December 6, 2002Publication date: October 23, 2003Inventors: Shenggao Liu, Robert M. Carlson, Jeremy E. Dahl, Waqar R. Qureshi
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Patent number: 6566559Abstract: Process for the production of unsaturated ethers, in particular isopropenyl methyl ether (IPM), by pyrolysis of a ketal-containing or acetal-containing mixture, in particular dimethoxypropane (DMP), in the liquid phase in the presence of an organic carboxylic acid, according to the following reaction scheme: wherein R1=H or alkyl with 1-8 C atoms; R2=H, CH3—, C2H5—, or Cl—; R3=alkyl with 1-8 C atoms; R4=H, CH3—, C2H5—, or C3H7—, and R1 and R4 may be joined to form a 5-, 6-, or 7-membered ring. DMP is produced by the process from acetone and methanol by reaction in an acidic heterogeneous ion exchanger, the product being isolated by extraction with aqueous alkaline solution. In particular the process involves combining the IPM reaction product with the DMP reaction product, which permits the execution of a stable recycling process in which the methanol-containing streams of the IPM and DMP stages can be simultaneously extracted.Type: GrantFiled: June 1, 2001Date of Patent: May 20, 2003Assignee: Degussa AGInventors: Steffen Krill, Stephan Kretz, Volker Häfner, Georg Markowz
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Patent number: 6559268Abstract: A perfluoro group-containing compound are represented by the following formula (I): —Rf— is a perfluoro group; and —A represents —OH or a group: or —CyF2y+1 or —CzF2z−1 and a perfluoro group-containing polymerizable compound represented by the following formula (II): R1—O—CH2—CH(OH)—CH2—O—Rf—B (II) In Formula (II), —Rf— is a perfluoro group; —B is —OH or —O—CH2—CH(OH)—CH2—O—R2, or —CyF2y+1 or —CzF2z−1; and R1 and R2 each is a dehydroxyl residue of a (meth)acryloyl group-containing compound or a vinyl group-containing compound. The hardened polymer from the compound has water-repellency, oil-repellency and adhering ability.Type: GrantFiled: March 17, 2000Date of Patent: May 6, 2003Assignee: Kyoeisha Chemcial Co., Ltd.Inventors: Junichi Ikeda, Hajimu Kawa
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Patent number: 6465059Abstract: The invention relates to a liquid-crystalline medium one or more compounds of the general formula IA and one or more compounds of the formula IB R, R*, R**, z, L and Y are defined herein.Type: GrantFiled: June 19, 2000Date of Patent: October 15, 2002Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Matthias Bremer, Georg Lüssem, Dagmar Klement
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Patent number: 6452060Abstract: The present invention relates to a method to prepare cyclopropenes.Type: GrantFiled: April 4, 2001Date of Patent: September 17, 2002Assignee: Rohm and Haas CompanyInventor: Richard Martin Jacobson
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Patent number: 6312618Abstract: A new class of asymmetric polar diphenyldiacetylene liquid crystal compounds and method for preparation are disclosed. The new class of liquid crystal compounds comprises the basic structure: Wherein R1 is an alkenyl group having the general formula (C2H2n−1), X is a cyano group, a fluoro group, CF3, OCF3, or a chloro group, Y1 is unsubstituted, a fluoro group, a chloro group or a methyl group, Y2 is unsubstituted, a fluoro group, a chloro group, or a methyl group, Z1 is unsubstituted, a fluoro group, or a methyl group, and Z2 is unsubstituted, a fluoro group, or a methyl group. The compounds disclosed exhibit high birefringence, low rotational viscosity, and have unexpectedly broad nematic ranges. Also disclosed are eutectic mixtures comprising at least one polar diphenyldiacetylene having the general structure described above. The eutectic mixtures also have unexpectedly broad nematic ranges.Type: GrantFiled: April 3, 2000Date of Patent: November 6, 2001Assignee: HRL LaboratoriesInventors: Shin-Tson Wu, Mary E. Neubert
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Patent number: 6310262Abstract: A new process prepares retiferol derivatives of formula I: wherein A is —C ≡C— or —CH═CH—, and R1 and R2 are independently of each other lower alkyl or lower perfluoroalkyl, one version couples ketones of formula 1I with compounds of formula III A second version couples phosphinoxides of formula IV with aldehydes of formula V. Compounds of formula I are useful in the treatment or prevention of hyperproliferative skin diseases and for reversing the conditions associated with photodamage.Type: GrantFiled: October 3, 2000Date of Patent: October 30, 2001Assignee: Basilea Pharmaceutica AGInventor: Hans Hilpert
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Patent number: 6309561Abstract: Fluorine-containing, chiral liquid crystal compounds comprise (a) a chiral fluorochemical terminal portion comprising (i) at least one chiral center, which can optionally be heteroatom-substituted; (ii) a terminal fluoroalkyl, fluoroether, perfluoroalkyl, or perfluoroether group; and (iii) an alkylene or fluoroalkylene group optionally containing at least one catenary ether oxygen atom; (b) a chiral or achiral terminal portion consisting of a hydrocarbon or hydrocarbon ether group, and, when chiral, comprising at least one chiral center, which can optionally be heteroatom-substituted; and (c) a central core connecting the terminal portions; the alkylene or fluoroalkylene group of the chiral fluorochemical terminal portion having at least 3 in-chain atoms and being located between the chiral center of the chiral fluorochemical terminal portion and the central core. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.Type: GrantFiled: December 24, 1997Date of Patent: October 30, 2001Assignee: 3M Innovative Properties CompanyInventors: Masakazu Hasegawa, Michael P. Keyes, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
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Patent number: 6300526Abstract: Hydro-2,2-difluoroalkylvinylethers having the formula CF2═CH—O—RA (I) wherein RA is a radical containing fluorine, optionally containing halogens such as Cl, Br, I, hydrogen, functional groups CM, COOR′, CON(R′)2, SO2OR′, m wherein R′ is a C1-C5 alkyl, RA being selected from the following: a linear or branched, saturated or unsaturated C2-C20 fluoroalkyl, or a saturated or unsaturated C4-C6 fluorinated cyclic group wherein optionally from 1 to 2 carbon atoms are substituted with oxygen atoms, or a linear, branched saturated or unsaturated, C3-C15 fluorooxyalkyl group, containing one or Core oxygen atoms.Type: GrantFiled: July 29, 1999Date of Patent: October 9, 2001Assignee: Austmont S.p.A.Inventors: Walter Navarrini, Antonio Russo
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Patent number: 6184422Abstract: Compounds of formula I wherein X is C═CH2 or CH2; Y and Z are independently of each other hydrogen, fluorine or hydroxy; A is —C≡C—, —CH═CH— or —CH2—CH2—, R1 and R2 are independently of each other alkyl or perfluoroalkyl; and R3 is lower alkyl are useful in the treatment or prevention of hyperproliferative skin diseases, particularly psoriasis, basal cell carcinomas, disorders of keratinization and keratosis; or for reversing the conditions associated with photodamage.Type: GrantFiled: February 18, 1999Date of Patent: February 6, 2001Assignee: Hoffman-La Roche Inc.Inventors: Pierre Barbier, Franz Bauer, Peter Mohr, Marc Muller, Wolfgang Pirson
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Patent number: 6133472Abstract: Fluorine containing oxyvinyl compounds characterized by having one or more oxyvinyl groups separated from fluorine containing groups by at least one alkylene group having 2-8 carbon atoms and by at least one oxygen atom in addition to the oxygen on the oxyvinyl. In general the compounds of the invention have the generic formula:Rz(L).sub.a (Ry).sub.b OROCH.dbd.CH.sub.2.Where L is .dbd.CHCOOROCH.dbd.CH.sub.2 ; a is number of 0 to about 1; R.sub.y is --CO--; b is a number of 0 to about 1; R is cycloalkane or (CH.sub.2).sub.x --, where x is a number of about 2 through about 10; R.sub.z is R.sub.f C.sub.n H.sub.m where R.sub.f is a fluorinated alkylene moiety of about 1 to about 12 carbon atoms which may be linear or branch chained and may contain a further --OROCH.dbd.CH.sub.2 group; n is an integer of about 1 through about 6; and m is an integer of n to 2n.Type: GrantFiled: January 20, 1998Date of Patent: October 17, 2000Assignee: AlliedSignal Inc.Inventors: David Nalewajek, David Bradley, John Schabel, Robert Blomquist
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Patent number: 6030547Abstract: Fluorine-containing, chiral liquid crystal compounds comprise (a) a chiral fluorochemical terminal portion comprising (i) at least one chiral center, which can optionally be heteroatom-substituted; (ii) a terminal fluoroalkyl, fluoroether, perfluoroalkyl, or perfluoroether group; and (iii) an alkylene or fluoroalkylene group optionally containing at least one caternary ether oxygen atom; (b) a chiral or achiral terminal portion consisting of a hydrocarbon or hydrocarbon ether group, and, when chiral, comprising at least one chiral center, which can optionally be heteroatom-substituted; and (c) a central core connecting the terminal portions; the alkylene or fluoroalkylene group of the chiral fluorochemical terminal portion having at least 3 in-chain atoms and being located between the chiral center of the chiral fluorochemical terminal portion and the central core. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.Type: GrantFiled: December 24, 1997Date of Patent: February 29, 2000Assignee: 3M Innovative Properties CompanyInventors: Masakazu Hasegawa, Michael P. Keyes, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
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Patent number: 5998674Abstract: Method of producing a bromine compound having an aliphatic unsaturated bond which includes reacting a compound having an aliphatic unsaturated bond represented by the following general formula (1) with bromine:R.sup.1 --O--Ar.sup.1 --Y--Ar.sup.2 --O--R.sup.2 (1)to produce a bromine compound represented by the following formula (2):R.sup.3 --O--Ar.sup.1 --Y--Ar.sup.2 --O--R.sup.4 (2)wherein Ar.sup.1, Ar.sup.2 and Y are the same as defined in the above general formula (1) , and R.sup.3 and R.sup.4 are groups obtained by saturating the unsaturated groups of R.sup.1 and R.sup.2 in the above general formula (1) with bromine, respectively.The reaction is carried out in the presence of a solvent which is inactive in the reaction, and a substantial amount of the heat of reaction is removed from a reaction system by the vaporization of the solvent or bromine. A high-purity bromine compound in high yield which is useful as flame retardant, can be obtained.Type: GrantFiled: August 21, 1998Date of Patent: December 7, 1999Assignee: Teijin Chemicals, Ltd.Inventors: Yutaka Taketani, Haruhisa Hoshimi, Masanori Monri, Seiichi Tanabe, Yasuhiro Shimidzu
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Patent number: 5972241Abstract: 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: November 6, 1997Date of Patent: October 26, 1999Assignee: 3M Innovative Properties CompanyInventors: Gilbert C. Johnson, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
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Patent number: 5969074Abstract: A reaction of perfluoroolefins with bis(silyl) ethers to produce novel partially fluorinated and perfluorinated copolymers and macrocyclic compounds is disclosed.Type: GrantFiled: May 21, 1993Date of Patent: October 19, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: William Brown Farnham, Mario Joseph Nappa
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Patent number: 5965779Abstract: The present invention provides processes for preparing 2,2,3,3,4-pentafluorooxetane and/or 2,2,3,3,4,4-hexafluorooxetane which comprises reacting 2,2,3,3-tetrafluorooxetane with fluorine gas, the process inhibiting decomposition of the oxetane ring during the reaction and producing a reduced amount of by-products.Type: GrantFiled: February 20, 1998Date of Patent: October 12, 1999Assignee: Daikin Industries, Ltd.Inventors: Tatsuya Otsuka, Hirokazu Aoyama
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Patent number: 5911912Abstract: Halovinyl ethers of the general formula I ##STR1## in which R, A.sup.1, A.sup.2, A.sup.3, Z.sup.1, Z.sup.2, X.sup.1, X.sup.2, l, m and n are as defined herein are suitable as components of liquid-crystalline media.Type: GrantFiled: November 20, 1997Date of Patent: June 15, 1999Assignee: Merck Patent Gesellschaft mit beschraenkter HaftungInventors: Peer Kirsch, Joachim Krause, Kazuaki Tarumi
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Patent number: 5723682Abstract: The invention relates to difluorovinyl ethers of the general formula I ##STR1## in which R, A, X and m are as defined in claim 1, and to the use of these compounds as components of liquid-crystalline media, and to liquid-crystal and electro-optical display elements which contain the novel liquid-crystalline media.Type: GrantFiled: March 5, 1997Date of Patent: March 3, 1998Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Eike Poetsch, Werner Binder, Michael Kompter, Joachim Krause, Kazuaki Tarumi, Ekkehard Bartmann
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Patent number: 5705713Abstract: Fluoro compounds are made by reaction of an activated oxy-acid ester or cyclic ether starting material with hydrogen fluoride in the presence of an organometallic compound.Type: GrantFiled: December 12, 1995Date of Patent: January 6, 1998Assignee: Rhone-Poulenc Chemicals LimitedInventors: Owen Ross Chambers, Patrick Charles Youmans
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Patent number: 5651919Abstract: Disclosed are a benzyl ether derivative represented by the following formula (I), useful as a liquid crystal display material, and a liquid crystal composition containing the same and a liquid crystal display device utilizing the composition. ##STR1## [wherein A represents a 4-alkylcyclohexyl group or an alkyl group, B represents a di- or tri-fluorophenyl group, a 4-(di- or tri-fluorophenyl)phenyl group, a 4-alkylphenyl group or a 4-alkoxyphenyl group].The compound (I) of the present invention has good compatibility with other compounds, and can be used in a liquid crystal composition by combining with many liquid crystal materials as a constitutional component of the liquid crystal composition. It has functions of lowering a C-N point of a liquid crystal composition, lowering a threshold voltage by enlarging a dielectric anisotropy, and also lowering a viscosity and increasing a N-I point of the liquid crystal composition.Type: GrantFiled: February 23, 1996Date of Patent: July 29, 1997Assignee: Citizen Watch Co., Ltd.Inventors: Tomijiro Naito, Yumiko Sakamaki, Hisato Sato
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Patent number: 5621144Abstract: New compounds are described typically having the formula CH.sub.3 C(CH.sub.2 R).sub.3 or ZCH.sub.2 C(CH.sub.2 R).sub.3 where R is a fluorohydrocarbon or perfluorocarbon group, preferably containing 4-16 carbon atoms and more F atoms that H atoms. Z is a hydrophilic group which may make the compound self-emulsifiable. The compounds are useful as oxygen transport agents in vivo, for which purpose aqueous emulsions are used, as a blood substitute.Type: GrantFiled: January 9, 1995Date of Patent: April 15, 1997Assignee: Isis Innovation LimitedInventor: Stephen R. Cooper
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Patent number: 5621147Abstract: A 1,1,2-trifluoro-2-(trans-4-substituted cyclohexyl)ethylene of the formula (1):R--(A).sub.m --Cy--CF=CF.sub.2 (1)wherein R is a C.sub.1-10 alkyl group, a halogen atom or a cyano group, provided that in the case of the alkyl group, an oxygen atom may be interposed in a carbon-carbon bond of the alkyl group or in a carbon-carbon bond between this alkyl group and A, some of carbon-carbon bonds in the alkyl group may be triple bonds or double bonds, one --CH.sub.2 -- group in the alkyl group may be substituted by a carbonyl group, and some or all of hydrogen atoms in the alkyl group may be substituted by fluorine atoms;Cy is an unsubstituted trans-1,4-cyclohexylene group;A is a trans-1,4-cyclohexylene group, a 1,4-phenylene group or a 1,4-cyclohexenylene group, wherein each of such cyclic groups is unsubstituted or substituted by one or more halogen atoms or cyano groups, one or more =CH-- groups constituting rings of such cyclic groups may be substituted by nitrogen atoms, and one or more --CH.sub.Type: GrantFiled: May 4, 1995Date of Patent: April 15, 1997Assignee: Asahi Glass Company Ltd.Inventors: Osamu Yokokoji, Tamaki Simizu, Seisaku Kumai
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Patent number: 5554316Abstract: A novel compound having superior characteristics as a liquid crystal material and having a good stability under usual use environment, and a composition having improved viscosity, optical anisotropy and other properties, and further a liquid crystal display element are provided,the compound being a hexenediyne compound expressed by the formula ##STR1## wherein R and R' each represent an alkyl group or an alkoxy group, independently of each other; rings A and B each represent 1,4-cyclohexylene or 1,4-phenylene; and X represents H or F), and particularly when fluorine atom is introduced into the central part of the molecule of the compound, the viscosity is notably lowered; and when a liquid crystal composition is composed of the compound as its component, the operation temperature range of the liquid crystal composition is broadened, and the high speed response becomes possible due to the viscosity reduction, and when the cell thickness is reduced, a good display can be realized.Type: GrantFiled: March 14, 1995Date of Patent: September 10, 1996Assignee: Chisso CorporationInventors: Atsuko Fujita, Shuichi Matsui, Kazutoshi Miyazawa, Yasuyuki Goto, Etsuo Nakagawa, Shinichi Sawada
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Patent number: 5545769Abstract: A process is disclosed for the manufacture of product compounds of the formula HC(R.sup.1).sub.2 C(R.sup.1).sub.2 C(R.sup.2).sub.2 H wherein each R.sup.1 is independently selected from the group consisting of H, F, Cl, CN, R, OR, CO.sub.2 R, C(O)R, OC(O)R, R.sup.f, OR.sup.f, CO.sub.2 R.sup.f, C(O)R.sup.f and OC(O)R.sup.f where R is a hydrocarbyl group and R.sup.f is a C.sub.1 to C.sub.10 polyfluoroalkyl group, provided that at least one R.sup.1 is F, and wherein each R.sup.2 is independently selected from the group consisting of H, F, Cl, CN, R, OR, CO.sub.2 R, C(O)R, OC(O)R, R.sup.f, OR.sup.f, CO.sub.2 R.sup.f, C(O)R.sup.f, OC(O)R.sup.f and difunctional linkages where an R.sup.2 group on each of two adjacent carbon atoms together form a link selected from the group consisting of --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH(CH.sub.3)--, --CH.sub.2 CH(CH.sub.3)CH.sub.2 --, --C(O)OC(O)--, and norborndiyl.Type: GrantFiled: September 29, 1994Date of Patent: August 13, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ralph T. Baker, Richard P. Beatty, William B. Farnham, Robert L. Wallace, Jr.
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Patent number: 5506309Abstract: This invention pertains to perfluoropolyethers and perhalogenated chlorofluoropolyethers that can be prepared by fluorinating addition polymers made by polymerizing epoxides.Type: GrantFiled: June 6, 1995Date of Patent: April 9, 1996Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhulke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5486636Abstract: New compounds of the formula ##STR1## where Y' represents hydroxy, protected-hydroxy, O-tosyl, O-mesyl, bromine, chlorine, or iodine and X.sup.1 and X.sup.2 may independently represent hydrogen or a hydroxy-protecting group are useful as intermediates for the production of 19-nor vitamin D derivatives, particularly 1.alpha.,25-dihydroxyvitamin D.sub.3, from (-)quinic acid.Type: GrantFiled: October 26, 1994Date of Patent: January 23, 1996Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Rolf E. Swenson
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Patent number: 5420359Abstract: Normally liquid chlorofluoroether compositions consisting or consisting essentially of one or a selected mixture of perhalogenated chlorofluoroether compounds are provided by direct fluorination of the corresponding chloroether or chlorofluoroether precursors. The compositions are useful, for example, as heat transfer agents, blood substitutes, and solvents.Type: GrantFiled: October 7, 1993Date of Patent: May 30, 1995Assignees: Minnesota Mining and Manufacturing Company, HemaGen/PFCInventors: George G. I. Moore, Richard M. Flynn, Robert J. Kaufman, Thomas J. Richard