Halogen In Alcohol Moiety Patents (Class 560/111)
  • Publication number: 20150132702
    Abstract: A method for fabricating a semiconductor product includes applying a photo-resist layer to a substrate, the photo-resist layer including a higher acid concentration at an upper portion of the photo-resist layer than at a lower portion of the photo-resist layer. The method also includes exposing the photo-resist layer to a light source through a mask including a feature, the photo-resist layer including a floating, diffusing acid that will diffuse into a region of the photo-resist layer affected by the feature while not diffusing into a feature formed by the mask.
    Type: Application
    Filed: January 16, 2015
    Publication date: May 14, 2015
    Inventors: Ching-Yu Chang, Ming-Feng Shieh, Wen-Hung Tseng
  • Patent number: 8742159
    Abstract: To provide a fluorinated compound having an RF group with at most 6 carbon atoms, whereby a fluorinated polymer having a highly durable water/oil repellency can be produced, and an environmental load is little, and a fluorinated polymer having a highly durable water/oil repellency and presenting little environmental load, obtainable by polymerizing such a fluorinated compound. A fluorinated compound represented by the following formula (I) and its polymer: CH2?C(M)COOXPhCOO(CH2)mCrF2r+1??(I) (in the formula (I), M is a hydrogen atom, a methyl group or a halogen atom, X is CHR1CH2O or CH2CHR1O, R1 is a C1-4 linear or branched alkyl group or CH2OR2, R2 is a C1-4 linear or branched alkyl group, Ph is a phenylene group, m is an integer of from 1 to 4, and r is an integer of from 1 to 6).
    Type: Grant
    Filed: September 14, 2012
    Date of Patent: June 3, 2014
    Assignee: Asahi Glass Company, Limited
    Inventor: Taiki Hoshino
  • Patent number: 8617789
    Abstract: A photoacid generator represented by the following formula (1), a method for producing the photoacid generator, and a resist composition containing the photoacid generator are provided. wherein in the formula (1), Y1, Y2, X, R1, R2, n1, n2 and A+ have the same meanings as defined in the detailed description of the invention. The photoacid generator can maintain an appropriate contact angle at the time of ArF liquid immersion lithography, can reduce defects occurring during liquid immersion lithography, and has excellent solubility in resist solvents and excellent compatibility with resins. Furthermore, the photoacid generator can be produced by an efficient and simple method using an epoxy compound that is industrially easily available.
    Type: Grant
    Filed: February 7, 2012
    Date of Patent: December 31, 2013
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Jung Hoon Oh, Jin Bong Shin, Tae Gon Kim, Dong Chul Seo
  • Patent number: 8471056
    Abstract: To provide a fluorinated compound having an RF group with at most 6 carbon atoms, whereby a fluorinated polymer having a highly durable water/oil repellency can be produced, and an environmental load is little, and a fluorinated polymer and a fluorinated copolymer having a highly durable water/oil repellency and presenting little environmental load, obtainable by polymerizing such a fluorinated compound. A fluorinated compound represented by the following formula (I) and its polymer: CH2?C(M)COO(CH2)nPhCOO(CH2)mCrF2r+1??(I) (in the formula (I), M is a hydrogen atom, a methyl group or a halogen atom, n is an integer of from 0 to 2, Ph is a phenylene group, m is an integer of from 1 to 4, and r is an integer of from 1 to 6).
    Type: Grant
    Filed: March 28, 2012
    Date of Patent: June 25, 2013
    Assignee: Asahi Glass Company, Limited
    Inventor: Taiki Hoshino
  • Publication number: 20130066091
    Abstract: A process for producing a chlorohydrin, an ester of a chlorohydrin, or a mixture thereof including the steps of contacting, in a hydrochlorination reactor, a multihydroxylated aliphatic hydrocarbon, an ester of a multihydroxylated aliphatic hydrocarbon, or a mixture thereof with a source of a hydrogen chloride, in the presence of a hydrophobic or extractable carboxylic acid catalyst is provided.
    Type: Application
    Filed: May 19, 2011
    Publication date: March 14, 2013
    Applicant: Dow Global Technologies LLC
    Inventors: Tina L. Arrowood, William J. Kruper, JR., John R. Briggs
  • Patent number: 8304513
    Abstract: Disclosed are polyesters, particularly poly(trimethylene terephthalate), comprising fluorovinylether functionalized aromatic repeat units, and methods to make the polyester polymers. The polymers are useful for imparting soil resistance to polyesters, particularly in the form of fibers, fabrics, and carpets.
    Type: Grant
    Filed: September 1, 2010
    Date of Patent: November 6, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventors: Neville Everton Drysdale, Surbhi Mahajan, Kenneth Gene Moloy, Fredrik Nederberg, Joel M. Pollino, Joachim C. Ritter
  • Patent number: 8188290
    Abstract: The present invention relates to a new and useful process for preparing N,N-substituted carbamoyl halides from secondary amines, carbon dioxide, trialkylsilyl chloride and a halogenating agent.
    Type: Grant
    Filed: October 26, 2006
    Date of Patent: May 29, 2012
    Assignee: Glaxo Group Limited
    Inventors: Ilaria Bientinesi, Zadeo Cimarosti, Giuseppe Guercio, Corinne Leroi, Alcide Perboni
  • Publication number: 20110313190
    Abstract: When sulfinating a carboxylic acid bromofluoroalkyl ester by using a sulfinating agent, an organic base is used, thereby obtaining a fluoroalkanesulfinic acid ammonium salt. This is oxidized to obtain a fluoroalkanesulfonic acid ammonium salt. This is used as the raw material and is converted to an onium salt or is converted to an onium salt by going through saponification and esterification, thereby obtaining a fluoroalkanesulfonic acid onium salt. This fluoroalkanesulfonic acid onium salt is useful as a photoacid generator used for chemically amplified resist materials, etc.
    Type: Application
    Filed: March 12, 2010
    Publication date: December 22, 2011
    Applicant: Central Glass Company, Limited
    Inventors: Masashi Nagamori, Yuji Hagiwara, Takashi Masubuchi, Satoru Narizuka
  • Publication number: 20110178323
    Abstract: Provided is a method for producing a tetrafluoro nitrogen-containing heterocyclic compound such as tetrafluoropyrrolidine in good yield and at low cost. The method comprises the steps of: (A) reacting a compound represented by the formula (I) with fluorine gas to produce a tetrafluoro compound represented by the formula (II), (B) converting the tetrafluoro derivative represented by the formula (II) to a compound represented by the formula (III), and (C) reacting the compound represented by the formula (III) with an amine compound represented by the formula NH2R9 to produce a tetrafluoro nitrogen-containing heterocyclic compound represented by the formula (IV) or salt thereof.
    Type: Application
    Filed: October 2, 2009
    Publication date: July 21, 2011
    Applicant: NIPPON SODA CO., LTD.
    Inventor: Yasuhiro Miyashita
  • Publication number: 20110088594
    Abstract: The present invention relates to compounds of the formulae (I), (II) and (III), to the use of compounds containing at least one perfluoro-tert-butoxy group and at least one substituted or unsubstituted aromatic end group as surface-active agent, and to a process for the preparation of compounds of the formula (II).
    Type: Application
    Filed: May 15, 2009
    Publication date: April 21, 2011
    Inventors: Eckhard Claus, Fanny Schooren, Martin Seidel, Wolfgang Hierse, Peer Kirsch
  • Publication number: 20110028725
    Abstract: The present disclosure provides methods of synthesizing alkylating agents and methods of use.
    Type: Application
    Filed: August 17, 2010
    Publication date: February 3, 2011
    Applicant: The Queen's Medical Center
    Inventor: John L. Lim
  • Publication number: 20100113818
    Abstract: An acid generator represented by the following formula (1) is provided: wherein X represents an alkylene group having 1 to 10 carbon atoms, —X1—O—X2—, or a heteroatom selected from the group consisting of nitrogen, sulfur and fluorine; X1 and X2 each independently represent an alkylene group having 1 to 10 carbon atoms; Y represents a cyclic hydrocarbon group having 5 to 30 carbon atoms and containing one or more aromatic rings, while one or more hydrogen atoms on the ring of the cyclic hydrocarbon group may be substituted by one or more members selected from the group consisting of —O—Y1, —CO—Y2, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, a perfluoroalkoxy group having 1 to 4 carbon atoms, a hydroxyalkyl group having 1 to 6 carbon atoms, a halogen atom, a hydroxyl group and a cyano group; Y1 and Y2 each independently represent an alkyl group having 1 to 6 carbon atoms; n represents an integer of 0 or 5; and A+
    Type: Application
    Filed: April 1, 2009
    Publication date: May 6, 2010
    Applicant: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Jung-Hoon Oh, Dong-Cheol Seo, Jin-Bong Shin
  • Patent number: 7615669
    Abstract: The present invention provides a process for producing highly pure fluoro-compounds by making use of N-(2-chloro-1,1,2-trifluoroethyl)diethylamine. The process produces little or no chlorinated by-products.
    Type: Grant
    Filed: March 22, 2006
    Date of Patent: November 10, 2009
    Assignee: Tosoh F-Tech, Inc.
    Inventors: Norihisa Kondo, Akio Watanabe, Hiroki Kanezaki, Kosuke Kawada
  • Patent number: 7560502
    Abstract: The invention describes a composition comprising a) an organic material which is susceptible to oxidative, thermal or light-induced degradation, and b) at least one melt additive of a compound of the formula I R1(I)R3XR2 wherein the general symbols are as defined in claim 1. The compounds of the formula I are useful as reducers of surface energy for organic materials, for example, for increasing the oil and water repellency of organic materials.
    Type: Grant
    Filed: January 30, 2006
    Date of Patent: July 14, 2009
    Assignee: Ciba Specialty Chemicals Corp.
    Inventors: Michèle Gerster, Manuel Mihalic, Armin Schneider
  • Publication number: 20090030228
    Abstract: The present invention provides a process for producing highly pure fluoro-compounds by making use of less costly and readily handleable N-(2-chloro-1,1,2-trifluoroethyl)diethylamine. The process produces little or no chlorinated by-products.
    Type: Application
    Filed: March 22, 2006
    Publication date: January 29, 2009
    Inventors: Norihisa Kondo, Akio Watanabe, Hiroki Kanezaki, Kosuke Kawada
  • Patent number: 7462734
    Abstract: The present invention relates to a process for producing an optically active ?-fluorocarboxylate derivative represented by the formula [2], by reacting an optically active ?-hydroxycarboxylate derivative with trifluoromethanesulfonyl fluoride (CF3SO2F) in the presence of an organic base, in the formula [2], R represents a straight-chain or branched-chain alkyl group of a carbon number of 1 to 12; one of or two by any combination of aromatic hydrocarbon groups, unsaturated hydrocarbon groups, straight-chain or branched alkoxy groups of a carbon number of 1 to 6, aryloxy groups, halogen atoms (fluorine, chlorine, bromine and iodine), protected carboxyl groups, protected amino groups or protected hydroxyl group can be substituted on any carbon atoms of the alkyl group; R1 represents a straight-chain or branched-chain alkyl group of a carbon number of 1 to 8; any carbon atoms of the alkyl groups of R and R1 may form a covalent bond; and * represents an asymmetric carbon.
    Type: Grant
    Filed: August 5, 2005
    Date of Patent: December 9, 2008
    Assignee: Central Glass Company, Limited
    Inventors: Akihiro Ishii, Hideyuki Tsuruta, Takashi Ootsuka, Yokusu Kuriyama, Manabu Yasumoto, Kenjin Inomiya, Koji Ueda
  • Publication number: 20080262234
    Abstract: The present invention relates to a new and useful process for preparing N,N-substituted carbamoyl halides from secondary amines, carbon dioxide, trialkylsilyl chloride and a halogenating agent.
    Type: Application
    Filed: October 26, 2006
    Publication date: October 23, 2008
    Inventors: Ilaria Bientinesi, Zadeo Cimarosti, Giuseppe Guercio, Corinne Leroi, Alcide Perboni
  • Publication number: 20080206820
    Abstract: The present invention provides methods for labeling One or two oxygen atom(s) in a carboxyl group of a carboxyl-containing compound with an oxygen isotope selected from oxygen-17 (17O) or oxygen-18 (18O). The methods of the present invention are characterized in that an activated ester of the carboxyl-containing compound (carboxylic acid) is reacted with H217O or H218O in the presence of an activator. In the methods of the present invention, the reaction between the activated ester of a carboxylic acid and H217O or H218O can be allowed to proceed without including drastic conditions such as strongly acidic conditions or alkaline hydrolysis because an activator is used.
    Type: Application
    Filed: May 20, 2005
    Publication date: August 28, 2008
    Inventors: Shigeyuki Yokoyama, Kazuhiko Yamada, Toshio Yamazaki
  • Publication number: 20080177102
    Abstract: In accordance with the present invention, a high intensity radiopaque contrast agent is disclosed. The agent may be coated on or incorporated within bulk materials, which may then be subsequently utilized to fabricate a radiopaque medical device. Primary effects through chemistry include higher radiopaque concentrations per unit weight of the radiopaque element or agent. Secondary effects include selective placement of the radiopaque elements which may further enhance the radiopacity of the device with reduced requirements of the radiopaque agent. Such a radiopaque contrast agent may be produced in various forms such as a dendrimer and/or incorporated as the end groups of polymeric chain. In addition one can incorporate biological and/or pharmaceutical agents in combination with the present invention.
    Type: Application
    Filed: March 19, 2008
    Publication date: July 24, 2008
    Inventor: Jonathon Z. Zhao
  • Patent number: 6989462
    Abstract: A process is described for preparing compounds of formula (I) where R is H, optionally halogen-substituted alkyl, cycloalkyl, aryl, alkyl-aryl or heteroaryl, and, in alkyl and cycloalkyl, one or more CH2 groups may be replaced by —O—. The compounds of the formula (I) are valuable intermediates in the synthesis of PPAR agonists.
    Type: Grant
    Filed: March 18, 2004
    Date of Patent: January 24, 2006
    Assignee: Sanofi-Aventis Deutschland GmbH
    Inventors: Claus-Jürgen Maier, Tobias Metzenthin, Joachim Graeser, Richard Bicker, Javier Manero
  • Patent number: 6972340
    Abstract: Compounds of formula (I) or therapeutically acceptable salts thereof, are selective protein tyrosine kinase-B (PTP1B) inhibitors. Preparation of the compounds, compositions containing the compounds, and treatment of disorders using the compounds are disclosed.
    Type: Grant
    Filed: August 29, 2001
    Date of Patent: December 6, 2005
    Assignee: Abbott Laboratories
    Inventors: Gang Liu, Bruce G. Szczepankiewicz, Zhonghua Pei, Zhili Xin, David A. Janowick
  • Patent number: 6946566
    Abstract: A process for preparing regioselectively an optically active 1-halogeno-2-hydroxypropyl compound of the following formula; wherein X is halogen atom and Nu is a heteroatom having a substituent, and an optically active glycidyl compound of the formula; which comprises reacting an optically active epihalohydrin of the formula; with a neucleophilic agent, in the presence of a metal complex of the formula; wherein n is an integer of 0, 1 or 2, Y1, Y2 and Y3 are hydrogen atom, etc., and Y2 and Y3 may form a ring such as benzene, A is a counterion and M is a metal ion, and further subjecting the compound (4) to reaction with a base to prepare the optically active glycidyl compound (5).
    Type: Grant
    Filed: July 30, 2003
    Date of Patent: September 20, 2005
    Assignee: Daiso Co., Ltd.
    Inventors: Keisuke Yaegashi, Yoshiro Furukawa
  • Patent number: 6753444
    Abstract: The invention relates to a process for preparing 2,3,5,6-tetrahaloxylylidene compounds of formula (I) where each Hal is independently fluorine or chlorine, and X is fluorine, chlorine, bromine, —O—R, or —O—C(═O)R, where R is hydrogen, a straight-chain or branched C1-C12-alkyl- or a C6-C14-aryl radical, by reacting 2,3,5,6-tetrahaloxylylidenediamines of formula (II) with an alkyl nitrite and/or nitrous acid in HX as a solvent.
    Type: Grant
    Filed: July 24, 2002
    Date of Patent: June 22, 2004
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Langer, Lars Rodefeld
  • Patent number: 6392089
    Abstract: Alcohol, phosphate, and diacid derivatives that may be deprotected by irradiation are disclosed. The protecting group is an arylacyl or heteroarylacyl group.
    Type: Grant
    Filed: March 31, 2000
    Date of Patent: May 21, 2002
    Assignee: University of Maryland
    Inventors: Daniel E. Falvey, Kwangjoo Lee, Anamitro Banerjee
  • Publication number: 20020028466
    Abstract: A novel approach using solid phase chemistry for scale-up was developed. The method makes use of high-load Merrifield resin.
    Type: Application
    Filed: May 4, 2001
    Publication date: March 7, 2002
    Inventors: Stephen P. Raillard, Gongjun Ji, Adam D. Mann, Ted A. Baer
  • Patent number: 6111130
    Abstract: The present invention relates to a process for the preparation of trifluoromethylated derivatives of the formula CF.sub.3 CCl.dbd.CHCH.sub.2 OC(.dbd.O)R, wherein R is unsubstituted or substituted C.sub.1 to C.sub.6 straight chain or branched alkyl, unsubstituted or substituted C.sub.3 to C.sub.7 cycloalkyl, unsubstituted or substituted C.sub.2 to C.sub.12 alkenyl, a benzyl group unsubstituted or substituted with R', a phenyl group unsubstituted or substituted with R'; R' is an unsubstituted or substituted C.sub.1 to C.sub.6 straight chain or branched alkyl; and wherein where R and/or R' are substituted each is substituted with R', by reaction of HCFC-353 with carboxylic acid salts. The trifluoromethylated derivatives, particularly CF.sub.3 CCl.dbd.CHCH.sub.2 OC(.dbd.O)CH.sub.3, are versatile intermediates for the synthesis of a wide variety of trifluoromethylated organic compounds, which find utility as pharmaceuticals, agricultural chemicals, and materials such as liquid crystals.
    Type: Grant
    Filed: May 10, 1999
    Date of Patent: August 29, 2000
    Assignee: AlliedSignal Inc.
    Inventor: Michael Van Der Puy
  • Patent number: 5756816
    Abstract: A process for the production of a phenol derivative of the formula (2), which comprises subjecting a diester compound of the formula (1) in which a hydroxyl group is protected by an acyl group, to a reaction for removal of protection, wherein the reaction is carried out in the presence of an aliphatic amine as a protection-removal agent, ##STR1## wherein X is hydrogen or fluorine, Y is --CH.sub.3 or --CF.sub.3, Q is an alkyl group having 1 to 4 carbon atoms, p is 0 or 1, m is an integer of 2 to 7, n is an integer of at least 1, and C* is an asymmetric carbon,the process enabling to obtain the phenol derivative of the formula (2) useful as an intermediate for a liquid crystal compound with ease and at high purity.
    Type: Grant
    Filed: January 29, 1997
    Date of Patent: May 26, 1998
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Yuki Motoyama, Tomoyuki Yui
  • Patent number: 5665877
    Abstract: The present invention provides a novel synthesis of the compounds of Formula (I): ##STR1## The compounds are produced in high yield and without utilizing expensive chromatographic separations. The synthesis is particularly advantageous because it is stereoselective.
    Type: Grant
    Filed: May 17, 1996
    Date of Patent: September 9, 1997
    Assignee: Eli Lilly and Company
    Inventors: Margaret M. Faul, Michael R. Jirousek, Leonard L. Winneroski, II
  • Patent number: 5614647
    Abstract: The present invention provides a novel synthesis of the compounds of Formula (I): ##STR1## The compounds are produced in high yield and without utilizing expensive chromatographic separations. The synthesis is particularly advantageous because it is stereoselective.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: March 25, 1997
    Assignee: Eli Lilly and Company
    Inventors: Margaret M. Faul, Michael R. Jirousek, Leonard L. Winneroski, II
  • Patent number: 5541347
    Abstract: The present invention provides a novel synthesis of the compounds of Formula (I): ##STR1## The compounds are produced in high yield and without utilizing expensive chromatographic separations. The synthesis is particularly advantageous because it is stereoselective.
    Type: Grant
    Filed: October 3, 1994
    Date of Patent: July 30, 1996
    Assignee: Eli Lilly and Company
    Inventors: Margaret M. Faul, Michael R. Jirousek, Leonard L. Winneroski II
  • Patent number: 5488133
    Abstract: Compounds having the structure ##STR1## wherein (Z--COO is the residue of an iodinated aromatic acid; n is an integer from 0 to 20;R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently H, alkyl, fluoroalkyl, cycloalkyl, aryl, aralkyl, alkoxy, aryloxy, halogen, hydroxy, acylamino, acetamidoalkyl, acetamidoaryl, --COO-alkyl, --COO-aryl, --COO-aralkyl, --CO-alkyl, --CO-aryl, --CO-heterocyclyl, cyano or heterocyclyl;R.sup.5 is H, alkyl, fluoroalkyl, cycloalkyl, aryl, aralkyl, alkoxyalkyl, heterocyclyl, or a Z-CO.sub.2 -CR.sup.1 R.sup.2 (CR.sup.3 R.sup.4).sub.n group, wherein Z, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and n are as defined above, m is an integer from 0 to 10, p is an integer from 0 to 10, and m+p.gtoreq.1 are useful as contrast agents in x-ray imaging compositions and methods.
    Type: Grant
    Filed: March 10, 1994
    Date of Patent: January 30, 1996
    Assignee: Eastman Kodak Company
    Inventors: Baldev Singh, Edward R. Bacon, Shaughnessy Robinson
  • Patent number: 5455371
    Abstract: A process for producing difluoromethyl ethers and esters by reacting an ether or an acid with a cadmium, zinc or bismuth compound containing the CF.sub.3 group and selected from the group consisting of Cd(CF.sub.3).sub.2, Zn(CF.sub.3).sub.2,Bi(CF.sub.3).sub.3, CdHal(CF.sub.3), ZnHal(CF.sub.3), BiHal(CF.sub.3).sub.2 and BiHal.sub.2 (CF.sub.3) in the presence of a Lewis acid.
    Type: Grant
    Filed: June 15, 1993
    Date of Patent: October 3, 1995
    Assignee: Solvay Fluor und Derivative GmbH
    Inventors: Dieter Naumann, Wieland Tyrra, Regina Moeckel
  • Patent number: 5453468
    Abstract: The invention relates to two classes of prepolymers containing a perfluoropolyethereal chain and carboxylic end groups, suitable as cross-linking agents for epoxy prepolymers. The first class contains anhydride-derived end groups; the second lactone-derived end groups; prepolymers therefrom are also disclosed. Additional non-fluorinated curing agents may also be added.
    Type: Grant
    Filed: January 24, 1995
    Date of Patent: September 26, 1995
    Assignee: Ausimont S.p.A.
    Inventors: Leno Mascia, Claudio Tonelli, Giovanni Simeone
  • Patent number: 5374376
    Abstract: 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: Grant
    Filed: September 21, 1993
    Date of Patent: December 20, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takayuki Higashii, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Shigeaki Chika, Koichi Fujisawa, Kiyoshi Imamura
  • Patent number: 5344638
    Abstract: Disclosed are contrast agents of the formula ##STR1## contained in aqueous compositions and methods for their use in diagnostic radiology of the gastrointestinal tract whereinwhereinZ=H, halo, C.sub.1 -C.sub.20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups;R=C.sub.1 -C.sub.25 alkyl, cycloalkyl, or halo-lower-alkyl, optionally substituted with halo, fluoro-lower-alkyl, aryl, lower-alkoxy, hydroxy, carboxy, lower-alkoxy carbonyl or lower-alkoxy-carbonyloxy, (CR.sub.1 R.sub.2).sub.p --(CR.sub.3 .dbd.CR.sub.4).sub.m Q, or (CR.sub.1 R.sub.2).sub.p --C.tbd.C--Q;R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently lower-alkyl, optionally substituted with halo;x is 1-3y is 1-4;n is 1-5;m is 1-15;p is 1-10; andQ is H, lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkylene, aryl, or aryl-lower alkylin an aqueous, pharmaceutically acceptable carrier.
    Type: Grant
    Filed: March 11, 1993
    Date of Patent: September 6, 1994
    Assignee: Sterling Winthrop Inc.
    Inventors: Carl R. Illig, Brent D. Douty
  • Patent number: 5292928
    Abstract: In a process for reacting a low molecular weight hydroxy compound with a carboxylic acid halide, a small amount of the acid halide is introduced into the reaction vessel and the remainder of the acid halide and the hydroxy compound are added gradually in an approximately stoichiometric ratio. The hydrogen halide formed is thus prevented from dissolving in the reaction medium. The heat of reaction to be dissipated is negligible.
    Type: Grant
    Filed: July 31, 1992
    Date of Patent: March 8, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Karlheinz Miltenberger
  • Patent number: 5275757
    Abstract: Novel anti-ferroelectric liquid crystal compounds represented by the following general formula (I) and a liquid crystal display element wherein such a compound is used. ##STR1## Ph represents a phenylene group, R represents a straight-chain alkyl group having 6 to 10 carbon atoms,X represents an oxygen atom or a single bond provided that when X is an oxygen atom, L is an integer of 5 to 8, m is 1 and n is an integer of 1 to 7, or L and m are zero (0) and n is an integer of 6 to 8, and when X is a single bond,L is an integer of 5 to 8, m is 1 and n is an integer of 1 to 7, andC* represents an asymmetric carbon atom.
    Type: Grant
    Filed: December 4, 1992
    Date of Patent: January 4, 1994
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hiroshi Mineta, Tomoyuki Yui, Takahiro Matsumoto
  • Patent number: 5254732
    Abstract: The invention describes N-fluorosulfonimides which are useful as fluorinating agents. The N-fluorosulfonimides are stable, easily synthesized, and allow the introduction of fluorine into organic compounds under mild conditions.
    Type: Grant
    Filed: February 28, 1992
    Date of Patent: October 19, 1993
    Assignee: Allied-Signal Inc.
    Inventor: Edmond Differding
  • Patent number: 5238603
    Abstract: A liquid crystal compound having specific features suitable to use for a display mode utilizing ferroelectric liquid crystals, particularly a large spontaneous polarization value and a liquid crystal composition using the compound are provided, which compound is an optically active liquid crystalline compound of the formula ##STR1## wherein l and m each are 0 or 1; at least one of R.sup.1 and R.sup.2 is an optically active alkoxy group of the formula ##STR2## wherein R.sup.3 is 2 or 3C alkyl and R.sup.4 is 3-18C alkyl, but R.sup.3 .noteq.R.sup.4 and the other thereof is 1-20C alkyl, alkoxy or alkanoyloxy, halogen or cyano; and A is a specified two or three rings compound.
    Type: Grant
    Filed: April 7, 1992
    Date of Patent: August 24, 1993
    Assignee: Chisso Corporation
    Inventors: Kazutoshi Miyazawa, Naoyuki Yoshida, Masakazu Kaneoya
  • Patent number: 5237087
    Abstract: A process for the preparation of chlorinated and fluorinated benzene compounds of the general formula (1) ##STR1## in which R denotes --CN or --COOalkyl(C.sub.1 -C.sub.6), and X and Y each denote chlorine or fluorine, X and Y being not identical, by fluorodenitration, which comprises reacting a compound of the formula (2) ##STR2## in which R is defined as above, and X' and Y' each denote chlorine or nitro, X' and Y' being nor identical, with potassium fluoride in a dipolar aprotic solvent in the presence of a transfer catalyst at a temperature from about 50.degree. C. to about 250.degree. C.
    Type: Grant
    Filed: September 21, 1992
    Date of Patent: August 17, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: James H. Clark, Andrew J. Beaumont, Nubia Boechat
  • Patent number: 5207946
    Abstract: A liquid crystal compound represented by formula (I): ##STR1## wherein R.sub.1 represents an alkyl group having from 3 to 18 carbon atoms; R.sub.2 represents an alkyl group having from 3 to 18 carbon atoms; X represents ##STR2## (A) and (B) each represents a group selected from the group consisting of ##STR3## and * indicates an optically active center.
    Type: Grant
    Filed: July 25, 1990
    Date of Patent: May 4, 1993
    Assignee: Showa Shell Sekiyu K.K.
    Inventors: Koichi Numazawa, Noriko Yamakawa, Yoshiichi Suzuki, Ichiro Kawamura
  • Patent number: 5175348
    Abstract: The invention relates to a novel process for the preparation of halogenated carboxylic acid esters of formula I ##STR1## wherein R.sub.1 is alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl or aryl, R.sub.2 hydrogen is alkyl or cycloalkyl, and R.sub.3 is halogen having an atomic number of from 9 up to and including 53, which process comprises reacting an acylal of formula II ##STR2## with a hydrogen halide of the formula H--R.sub.3 (III).
    Type: Grant
    Filed: March 10, 1992
    Date of Patent: December 29, 1992
    Assignee: Saurefabrik Schweizerhall
    Inventors: Pasquale Gallegra, Gerhard Degischer
  • Patent number: 5171879
    Abstract: The invention relates to a novel process for the preparation of chlorinated carboxylic acid esters of formula I ##STR1## wherein R.sub.1 is alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl or aryl and R.sub.2 hydrogen is alkyl or cycloalkyl, which process comprises reacting an acylal of formula II ##STR2## with thionyl chloride.
    Type: Grant
    Filed: March 10, 1992
    Date of Patent: December 15, 1992
    Assignee: Saurefabrik Schweizerhall
    Inventors: Pasquale Gallegra, Gerhard Degischer
  • Patent number: 5149843
    Abstract: Conjugated diene compounds of the general formula: ##STR1## which are industrially advantageous intermediates for preparing sarcophytol A useful as an anticarcinogenic promotor or antitumor agent are provided.
    Type: Grant
    Filed: June 7, 1991
    Date of Patent: September 22, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
  • Patent number: 5136061
    Abstract: An optically active pentane compound of the general formula (I): ##STR1## wherein R.sub.1 represents a lower alkyl group having 1 to 4 carbon atoms, R.sub.2 represents a lower alkoxycarbonyl group having an alkoxy moiety of 1 to 4 carbon atoms, or a straight-chain or branched alkyl group having 1 to 7 carbon atoms which is unsubstituted or substituted with a hydroxy or protected hydroxy group, A represents a halogen atom, hydroxy, protected hydroxy, or ethynyl group, or a group of the formula ##STR2## B represents a hydrogen atom, hydroxy, protected hydroxy or acyloxy group, D represents a hydrogen atom, or A and B together can form an acetal or epoxy group, A and D together can form an ethylidene group, and B and D together can form a carbon-carbon direct bond, and a chiral central carbon atoms marked with symbols *, # and .thrfore. in said formula (I) alternatively have one of an R-configuration and an S-configuration.
    Type: Grant
    Filed: June 13, 1991
    Date of Patent: August 4, 1992
    Assignee: Asahi Denka Kogyo K.K.
    Inventors: Seiichi Takano, Kunio Ogasawara
  • Patent number: 5124070
    Abstract: 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: Grant
    Filed: August 28, 1989
    Date of Patent: June 23, 1992
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takayuki Higashii, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Takeshi Tani, Chizu Kawakami, Koichi Fujisawa, Kiyoshi Imamura
  • Patent number: 5098602
    Abstract: 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: Grant
    Filed: May 2, 1989
    Date of Patent: March 24, 1992
    Assignee: Nippon Mining Co., Ltd.
    Inventors: Toshihiro Hirai, Atsushi Yoshizawa, Isa Nishiyama, Mitsuo Fukumasa, Nobuyuki Shiratori, Akihisa Yokoyama
  • Patent number: 5011943
    Abstract: A process is described for the improved synthesis of the optically pure C.sub.10 -C.sub.24 fragment of the macrolide structure of the immunosuppressant FK-506. This compound is also useful as an intermediate for preparing FK-506 derivatives.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: April 30, 1991
    Assignee: Merck Frosst Canada, Inc.
    Inventor: Zhaoyin Wang
  • Patent number: 4999454
    Abstract: The invention is directed to a new process for the preparation of carbinols of the general formula I ##STR1## by reaction chloral and olefins of the general formula ##STR2## and by optional acylation of the product comprising dissolving a catalyst of the general formula IIIFe.sub.n (NH.sub.4).sub.x Y.sub.m .multidot.A.sub.p IIIin chloral, then adding the olefin of the general formula II in order to produce a complex of the general formula IV ##STR3## from which a complex of the general formula V ##STR4## is formed, and from the reaction mixture a compound of the general formula I is obtained whereafter(a) the residual complex of the general formula V dissolved in the product is decomposed with an acidic solution and if desired the obtained product is distilled or(b) the product in the reaction mixture is acylated.The compounds prepared according to the invention can be utilized as intermediates when preparing e.g., permethrin and other pyrethroid insecticides.
    Type: Grant
    Filed: October 3, 1985
    Date of Patent: March 12, 1991
    Assignee: Chinoin Gyogyszer ES Vegyeszeti Termekek Gyara RT.
    Inventors: Rudolf Soos, Jozsef Nemes, Miklos Szelestei, Istvan Schler, Laszlo Vidra, Istvan Szekely
  • Patent number: 4985588
    Abstract: A process for producing nucleus-fluorinated aromatic carboxylates, which comprise nucleus-fluorinating aromatic carboxylates of the following formula (1) with a fluorinating agent to obtain nucleus-fluorinated aromatic carboxylates of the following formula (2): ##STR1## wherein R.sup.1 is an alkyl group, an aryl group or a fluoroalkyl group, each of A and B is at least one member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group, an aryl group and a fluoroalkyl group, and n and m are integers satisfying m+n=6, provided that m is 1 or 2, provided that at least one A is an activated chlorine or bromine atom, and B corresponding to such an activated chlorine or bromine atom is a fluorine atom.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: January 15, 1991
    Assignee: Asahi Glass Company Ltd.
    Inventors: Seisaku Kumai, Osamu Yokokouji