Halogen In Alcohol Moiety Patents (Class 560/111)
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Publication number: 20150132702Abstract: 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: ApplicationFiled: January 16, 2015Publication date: May 14, 2015Inventors: Ching-Yu Chang, Ming-Feng Shieh, Wen-Hung Tseng
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Patent number: 8742159Abstract: 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: GrantFiled: September 14, 2012Date of Patent: June 3, 2014Assignee: Asahi Glass Company, LimitedInventor: Taiki Hoshino
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Patent number: 8617789Abstract: 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: GrantFiled: February 7, 2012Date of Patent: December 31, 2013Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Jung Hoon Oh, Jin Bong Shin, Tae Gon Kim, Dong Chul Seo
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Patent number: 8471056Abstract: 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: GrantFiled: March 28, 2012Date of Patent: June 25, 2013Assignee: Asahi Glass Company, LimitedInventor: Taiki Hoshino
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Publication number: 20130066091Abstract: 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: ApplicationFiled: May 19, 2011Publication date: March 14, 2013Applicant: Dow Global Technologies LLCInventors: Tina L. Arrowood, William J. Kruper, JR., John R. Briggs
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Patent number: 8304513Abstract: 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: GrantFiled: September 1, 2010Date of Patent: November 6, 2012Assignee: E I du Pont de Nemours and CompanyInventors: Neville Everton Drysdale, Surbhi Mahajan, Kenneth Gene Moloy, Fredrik Nederberg, Joel M. Pollino, Joachim C. Ritter
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Patent number: 8188290Abstract: 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: GrantFiled: October 26, 2006Date of Patent: May 29, 2012Assignee: Glaxo Group LimitedInventors: Ilaria Bientinesi, Zadeo Cimarosti, Giuseppe Guercio, Corinne Leroi, Alcide Perboni
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Publication number: 20110313190Abstract: 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: ApplicationFiled: March 12, 2010Publication date: December 22, 2011Applicant: Central Glass Company, LimitedInventors: Masashi Nagamori, Yuji Hagiwara, Takashi Masubuchi, Satoru Narizuka
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Publication number: 20110178323Abstract: 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: ApplicationFiled: October 2, 2009Publication date: July 21, 2011Applicant: NIPPON SODA CO., LTD.Inventor: Yasuhiro Miyashita
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Publication number: 20110088594Abstract: 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: ApplicationFiled: May 15, 2009Publication date: April 21, 2011Inventors: Eckhard Claus, Fanny Schooren, Martin Seidel, Wolfgang Hierse, Peer Kirsch
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Publication number: 20110028725Abstract: The present disclosure provides methods of synthesizing alkylating agents and methods of use.Type: ApplicationFiled: August 17, 2010Publication date: February 3, 2011Applicant: The Queen's Medical CenterInventor: John L. Lim
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Publication number: 20100113818Abstract: 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: ApplicationFiled: April 1, 2009Publication date: May 6, 2010Applicant: Korea Kumho Petrochemical Co., Ltd.Inventors: Jung-Hoon Oh, Dong-Cheol Seo, Jin-Bong Shin
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Patent number: 7615669Abstract: 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: GrantFiled: March 22, 2006Date of Patent: November 10, 2009Assignee: Tosoh F-Tech, Inc.Inventors: Norihisa Kondo, Akio Watanabe, Hiroki Kanezaki, Kosuke Kawada
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Functionalized esters, amides or urethanes of perfluorinated alcohols or amines as surface modifiers
Patent number: 7560502Abstract: 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: GrantFiled: January 30, 2006Date of Patent: July 14, 2009Assignee: Ciba Specialty Chemicals Corp.Inventors: Michèle Gerster, Manuel Mihalic, Armin Schneider -
Publication number: 20090030228Abstract: 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: ApplicationFiled: March 22, 2006Publication date: January 29, 2009Inventors: Norihisa Kondo, Akio Watanabe, Hiroki Kanezaki, Kosuke Kawada
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Patent number: 7462734Abstract: 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: GrantFiled: August 5, 2005Date of Patent: December 9, 2008Assignee: Central Glass Company, LimitedInventors: Akihiro Ishii, Hideyuki Tsuruta, Takashi Ootsuka, Yokusu Kuriyama, Manabu Yasumoto, Kenjin Inomiya, Koji Ueda
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Publication number: 20080262234Abstract: 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: ApplicationFiled: October 26, 2006Publication date: October 23, 2008Inventors: Ilaria Bientinesi, Zadeo Cimarosti, Giuseppe Guercio, Corinne Leroi, Alcide Perboni
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Publication number: 20080206820Abstract: 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: ApplicationFiled: May 20, 2005Publication date: August 28, 2008Inventors: Shigeyuki Yokoyama, Kazuhiko Yamada, Toshio Yamazaki
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Publication number: 20080177102Abstract: 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: ApplicationFiled: March 19, 2008Publication date: July 24, 2008Inventor: Jonathon Z. Zhao
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Patent number: 6989462Abstract: 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: GrantFiled: March 18, 2004Date of Patent: January 24, 2006Assignee: Sanofi-Aventis Deutschland GmbHInventors: Claus-Jürgen Maier, Tobias Metzenthin, Joachim Graeser, Richard Bicker, Javier Manero
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Patent number: 6972340Abstract: 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: GrantFiled: August 29, 2001Date of Patent: December 6, 2005Assignee: Abbott LaboratoriesInventors: Gang Liu, Bruce G. Szczepankiewicz, Zhonghua Pei, Zhili Xin, David A. Janowick
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Patent number: 6946566Abstract: 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: GrantFiled: July 30, 2003Date of Patent: September 20, 2005Assignee: Daiso Co., Ltd.Inventors: Keisuke Yaegashi, Yoshiro Furukawa
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Patent number: 6753444Abstract: 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: GrantFiled: July 24, 2002Date of Patent: June 22, 2004Assignee: Bayer AktiengesellschaftInventors: Reinhard Langer, Lars Rodefeld
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Patent number: 6392089Abstract: Alcohol, phosphate, and diacid derivatives that may be deprotected by irradiation are disclosed. The protecting group is an arylacyl or heteroarylacyl group.Type: GrantFiled: March 31, 2000Date of Patent: May 21, 2002Assignee: University of MarylandInventors: Daniel E. Falvey, Kwangjoo Lee, Anamitro Banerjee
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Publication number: 20020028466Abstract: A novel approach using solid phase chemistry for scale-up was developed. The method makes use of high-load Merrifield resin.Type: ApplicationFiled: May 4, 2001Publication date: March 7, 2002Inventors: Stephen P. Raillard, Gongjun Ji, Adam D. Mann, Ted A. Baer
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Patent number: 6111130Abstract: 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: GrantFiled: May 10, 1999Date of Patent: August 29, 2000Assignee: AlliedSignal Inc.Inventor: Michael Van Der Puy
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Patent number: 5756816Abstract: 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: GrantFiled: January 29, 1997Date of Patent: May 26, 1998Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Yuki Motoyama, Tomoyuki Yui
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Patent number: 5665877Abstract: 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: GrantFiled: May 17, 1996Date of Patent: September 9, 1997Assignee: Eli Lilly and CompanyInventors: Margaret M. Faul, Michael R. Jirousek, Leonard L. Winneroski, II
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Patent number: 5614647Abstract: 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: GrantFiled: May 25, 1995Date of Patent: March 25, 1997Assignee: Eli Lilly and CompanyInventors: Margaret M. Faul, Michael R. Jirousek, Leonard L. Winneroski, II
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Patent number: 5541347Abstract: 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: GrantFiled: October 3, 1994Date of Patent: July 30, 1996Assignee: Eli Lilly and CompanyInventors: Margaret M. Faul, Michael R. Jirousek, Leonard L. Winneroski II
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Patent number: 5488133Abstract: 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: GrantFiled: March 10, 1994Date of Patent: January 30, 1996Assignee: Eastman Kodak CompanyInventors: Baldev Singh, Edward R. Bacon, Shaughnessy Robinson
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Patent number: 5455371Abstract: 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: GrantFiled: June 15, 1993Date of Patent: October 3, 1995Assignee: Solvay Fluor und Derivative GmbHInventors: Dieter Naumann, Wieland Tyrra, Regina Moeckel
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Patent number: 5453468Abstract: 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: GrantFiled: January 24, 1995Date of Patent: September 26, 1995Assignee: Ausimont S.p.A.Inventors: Leno Mascia, Claudio Tonelli, Giovanni Simeone
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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: 5344638Abstract: 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: GrantFiled: March 11, 1993Date of Patent: September 6, 1994Assignee: Sterling Winthrop Inc.Inventors: Carl R. Illig, Brent D. Douty
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Patent number: 5292928Abstract: 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: GrantFiled: July 31, 1992Date of Patent: March 8, 1994Assignee: Hoechst AktiengesellschaftInventor: Karlheinz Miltenberger
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Patent number: 5275757Abstract: 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: GrantFiled: December 4, 1992Date of Patent: January 4, 1994Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hiroshi Mineta, Tomoyuki Yui, Takahiro Matsumoto
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Patent number: 5254732Abstract: 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: GrantFiled: February 28, 1992Date of Patent: October 19, 1993Assignee: Allied-Signal Inc.Inventor: Edmond Differding
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Patent number: 5238603Abstract: 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: GrantFiled: April 7, 1992Date of Patent: August 24, 1993Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Naoyuki Yoshida, Masakazu Kaneoya
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Patent number: 5237087Abstract: 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: GrantFiled: September 21, 1992Date of Patent: August 17, 1993Assignee: Hoechst AktiengesellschaftInventors: James H. Clark, Andrew J. Beaumont, Nubia Boechat
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Patent number: 5207946Abstract: 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: GrantFiled: July 25, 1990Date of Patent: May 4, 1993Assignee: Showa Shell Sekiyu K.K.Inventors: Koichi Numazawa, Noriko Yamakawa, Yoshiichi Suzuki, Ichiro Kawamura
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Patent number: 5175348Abstract: 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: GrantFiled: March 10, 1992Date of Patent: December 29, 1992Assignee: Saurefabrik SchweizerhallInventors: Pasquale Gallegra, Gerhard Degischer
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Patent number: 5171879Abstract: 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: GrantFiled: March 10, 1992Date of Patent: December 15, 1992Assignee: Saurefabrik SchweizerhallInventors: Pasquale Gallegra, Gerhard Degischer
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Patent number: 5149843Abstract: 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: GrantFiled: June 7, 1991Date of Patent: September 22, 1992Assignee: Mitsubishi Kasei CorporationInventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
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Patent number: 5136061Abstract: 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: GrantFiled: June 13, 1991Date of Patent: August 4, 1992Assignee: Asahi Denka Kogyo K.K.Inventors: Seiichi Takano, Kunio Ogasawara
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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: 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: 5011943Abstract: 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: GrantFiled: August 28, 1989Date of Patent: April 30, 1991Assignee: Merck Frosst Canada, Inc.Inventor: Zhaoyin Wang
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Patent number: 4999454Abstract: 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: GrantFiled: October 3, 1985Date of Patent: March 12, 1991Assignee: Chinoin Gyogyszer ES Vegyeszeti Termekek Gyara RT.Inventors: Rudolf Soos, Jozsef Nemes, Miklos Szelestei, Istvan Schler, Laszlo Vidra, Istvan Szekely
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Patent number: 4985588Abstract: 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: GrantFiled: August 28, 1989Date of Patent: January 15, 1991Assignee: Asahi Glass Company Ltd.Inventors: Seisaku Kumai, Osamu Yokokouji