The Cyano Group Is Bonded Directly To The Carbon Adjacent To The Carbonyl Carbon (e.g., Alpha Cyano Acrylates, Etc.) Patents (Class 558/443)
  • Patent number: 11597695
    Abstract: A method of preparing an ester by reacting a carboxylic acid with a (C1-C36)alcohol in the presence of a catalyst that is suitable for preparing carboxylic acid esters of monomeric carboxylic acids in high yield. The method reduces by-products of the reaction, in particular esters of dimeric, trimeric and/or oligomeric carboxylic acids. The method requires a minimal excess of alcohol and does not require removal of water and/or carboxylic acid ester from the reaction mixture. The method is particularly suitable for the reaction of hydroxyalkylcarboxylic acids and fatty alcohols.
    Type: Grant
    Filed: October 11, 2017
    Date of Patent: March 7, 2023
    Assignee: BASF SE
    Inventors: Miriam Kolk, Konstantinos Scholinakis, Eike Ulf Mahnke, Lutz Hilterhaus, Volker Winterhoff
  • Patent number: 10159912
    Abstract: Methods of processing distillates, methods of removing at least some portion of total phosphorus in a distillate, methods of removing at least some portion of the soluble inorganic phosphorus, phytate phosphorus, or some combination thereof in a distillate, methods for obtaining phytate from distillates, methods for producing phytate derivatives and combinations thereof.
    Type: Grant
    Filed: May 6, 2016
    Date of Patent: December 25, 2018
    Assignee: REGENTS OF THE UNIVERSITY OF MINNESOTA
    Inventors: Bo Hu, Qiyang He
  • Patent number: 9296684
    Abstract: An allyl 2-cyanoacrylate prepolymer, a preparation method thereof, and a bioadhesive composition including the prepolymer thus produced are provided, and more particularly, an allyl 2-cyanoacrylate prepolymer having a structure, in which at least one double bond in a molecule remains at an adjacent site to a cyano group prepared by causing a prepolymerization in a double bond moiety of an allyl group by pre-polymerizing through heating 2-cyanoacrylate having at least two double bonds in a molecule such as allyl 2-cyanoacrylate, a method for preparing the same, and a bioadhesive composition including the prepolymer thus produced are provided.
    Type: Grant
    Filed: November 6, 2012
    Date of Patent: March 29, 2016
    Assignee: UNIVERSITY-INDUSTRY COOPERATION GROUP OF KYUNG HEE UNIVERSITY
    Inventors: Hun Kuk Park, Jin Ik Lim, Ji Hye Kim
  • Patent number: 8975433
    Abstract: Provided is a 2-cyanoacrylate-purifying method for decoloring a 2-cyanoacrylate which has been colored, and preventing further coloring of the 2-cyanoacrylate thus decolored. The 2-cyanoacrylate-purifying method includes the steps of: (a) adding a specific polyhydric aromatic compound to the 2-cyanoacrylate which has been colored; and (b) storing, at a temperature in a range of 0° C. to 40° C. for 0.5 day or more, the resulting mixture obtained in the step (a), and then subjecting the mixture to reduced pressure distillation.
    Type: Grant
    Filed: February 24, 2012
    Date of Patent: March 10, 2015
    Assignee: Taoka Chemical Co., Ltd.
    Inventors: Yoshio Nagahama, Yukinori Nishino, Hiroaki Yamamoto
  • Patent number: 8927557
    Abstract: The compounds of Formula (I), wherein R1, R2, R21, R22, R23, R24, Y and R3 have the meanings as given in the description, the salts thereof, the stereoisomers of the compounds and the salts thereof are effective inhibitors of the type 5 phosphodiesterase.
    Type: Grant
    Filed: August 24, 2010
    Date of Patent: January 6, 2015
    Assignee: Takeda GmbH
    Inventors: Josef Stadlwieser, Beate Schmidt, Heiko Bernsmann, Torsten Dunkern, Ewald Benediktus, Andreas Pahl, Ragna Hussong, Olaf Nimz, Matthias Mueller, Martin Viertelhaus
  • Patent number: 8829225
    Abstract: An improvement in the production of 1,1-disubstituted ethylenes is attained by contacting a 1,1-disubstituted ethylene with alumina and separating the alumina to obtain a 1,1-disubstituted ethylene with a good combination of cost, purity, shelf life and cure rate.
    Type: Grant
    Filed: January 28, 2013
    Date of Patent: September 9, 2014
    Assignee: OptMed, Inc.
    Inventors: Francis McConville, John Gregory Reid, Murugappa Vedachalam
  • Patent number: 8829192
    Abstract: Described is the use of specific merocyanine derivatives for protecting body-care and household products from photolytic and oxidative degradation. These compounds perform outstanding UV absorber properties.
    Type: Grant
    Filed: July 19, 2006
    Date of Patent: September 9, 2014
    Assignee: BASF SE
    Inventors: Barbara Wagner, Oliver Reich
  • Publication number: 20140150380
    Abstract: Disclosed are compounds of formula (1) and (2) and/or E/E-, E/Z- or Z/Z geometrical isomer forms thereof; wherein R1-R5, R1-R11 and A are defined as in description. The compounds are used as UV absorbers for protecting household products from photolytic and oxidative degradation, as plastic additives, preferably for food and pharmaceutical packaging applications, for preventing photo-degradation of food by incorporation of the compounds of formula (1?) and/or (2?) into transparent food containers, for protection of UV-A sensitive drugs from photo-degradation by incorporation of UV absorber in transparent blister foils or transparent pharmacy containers, as additives for photographic and printing applications, as additives for electronic applications and protecting the ingredients in agriculture applications.
    Type: Application
    Filed: July 19, 2012
    Publication date: June 5, 2014
    Inventors: Barbara Winkler, Dietmar Hueglin, Kai Eichin, Larissa Ehrsam, Xavier Marat, Hervé Richard, ILona Marion Kienzle, Ute Schroeder
  • Publication number: 20140051881
    Abstract: The present disclosure provides a process for preparing 2,3-dicyanopropionic acid ester of formula (I); said process comprising the following steps: i) treating an alkali metal cyanide dissolved in a solvent with a solution of 2-cyano-2-propenoic acid ester of formula (II) at a temperature ranging between 0° C. and 50° C. for a time period ranging between 2 hours and 15 hours followed by cooling below 20° C.
    Type: Application
    Filed: October 24, 2013
    Publication date: February 20, 2014
    Inventor: Keki Hormusji GHARDA
  • Publication number: 20130331598
    Abstract: Provided is a 2-cyanoacrylate-purifying method for decoloring a 2-cyanoacrylate which has been colored, and preventing further coloring of the 2-cyanoacrylate thus decolored. The 2-cyanoacrylate-purifying method includes the steps of: (a) adding a specific polyhydric aromatic compound to the 2-cyanoacrylate which has been colored; and (b) storing, at a temperature in a range of 0° C. to 40° C. for 0.5 day or more, the resulting mixture obtained in the step (a), and then subjecting the mixture to reduced pressure distillation.
    Type: Application
    Filed: February 24, 2012
    Publication date: December 12, 2013
    Applicant: TAOKA CHEMICAL CO., LTD.
    Inventors: Yoshio Nagahama, Yukinori Nishino, Hiroaki Yamamoto
  • Publication number: 20130310594
    Abstract: An improvement in the production of 1,1-disubstituted ethylenes is attained by contacting a 1,1-disubstituted ethylene with alumina and separating the alumina to obtain a 1,1-disubstituted ethylene with a good combination of cost, purity, shelf life and cure rate.
    Type: Application
    Filed: January 28, 2013
    Publication date: November 21, 2013
    Applicant: OptMed, Inc.
    Inventors: Francis McConville, John Gregory Reid, Murugappa Vedachalam
  • Publication number: 20130253213
    Abstract: Provided is a method for producing cyanoacetic acid in a hydrolysis reaction of a predetermined cyanoacetate in the presence of an acid catalyst. Further, are provided methods for producing a cyanoacetic acid derivative and a metal containing compound by using the produced cyanoacetic acid as a staring material. Herein, the method for producing cyanoacetic acid enables the content of a malonic acid byproduct generated in the hydrolysis reaction to be greatly lowered, allowing the produced cyanoacetic acid to be used as a starting material without any purification treatments. Those advantageous effects result in the great improvement in the purity and yields of the cyanoacetic acid derivative and the metal containing compound produced by said cyanoacetic acid. Accordingly, the above mentioned methods make it possible to produce cyanoacetic acid, the cyanoacetic acid derivative and the metal containing compound, as excellent in the productivity and economical efficiency.
    Type: Application
    Filed: March 15, 2013
    Publication date: September 26, 2013
    Applicant: Konica Minolta Business Technologies, Inc.
    Inventors: Dai IKEMIZU, Ryohei IWAMOTO, Keiko ISHIDAI, Kimihiko OOKUBO
  • Publication number: 20130178426
    Abstract: The invention has as its object the provision of a medicine capable of reducing a volume of emphysema-suffering pulmonary alveoli or alveolar sacs by means of a respiratory region volume inhibitor containing a coating film formation as a main component and capable of forming a coating film in a respiratory region, characterized by being used in such a way that the coating film-forming component is administered to an emphysema-suffering pulmonary alveolar parenchyma in a human-respiratory region in an amount of 0.004 to 200 g/application, preferably 0.07 to 20 g/application and more preferably 0.5 to 5 g/application on each occasion.
    Type: Application
    Filed: August 10, 2011
    Publication date: July 11, 2013
    Applicant: Terumo Kabushiki Kaisha
    Inventors: Takao Anzai, Atsuhiko Nogawa, Yuichi Tada
  • Patent number: 8455544
    Abstract: The present invention concerns methods for treating and preventing renal/kidney disease, insulin resistance/diabetes, fatty liver disease, and/or endothelial dysfunction/cardiovascular disease using synthetic triterpenoids, optionally in combination with a second treatment or prophylaxis.
    Type: Grant
    Filed: January 26, 2012
    Date of Patent: June 4, 2013
    Assignees: Reata Pharmaecuticals, Inc., Trustees of Dartmouth College
    Inventors: Michael B. Sporn, Karen T. Liby, Gordon W. Gribble, Tadashi Honda, Robert M. Kral, Colin J. Meyer
  • Publication number: 20130064871
    Abstract: The present invention relates to a cosmetic composition comprising the combination i) of at least one screening agent of the dibenzoylmethane derivative type and ii) of at least one specific merocyanine dicyano or cyanoacetate derivative. It also relates to a method for the photostabilization, with regard to radiation, of at least one screening agent of the dibenzoylmethane derivative type by an effective amount of at least one specific merocyanine dicyano or cyanoacetate derivative.
    Type: Application
    Filed: March 7, 2011
    Publication date: March 14, 2013
    Applicant: L'OREAL
    Inventors: Herve Richard, Benoit Muller
  • Patent number: 8329936
    Abstract: The present invention relates to a method for producing cyanoacrylic acid esters. The method is based substantially on a transesterification reaction, wherein the transesterification reaction is performed in the presence of at least one transition metal catalyst that is formed by reacting at least one hydroxyl group-containing support material with at least one transition metal alkoxide.
    Type: Grant
    Filed: January 3, 2012
    Date of Patent: December 11, 2012
    Assignee: Henkel AG & Co. KGaA
    Inventors: Carsten Friese, Andreas Kirschning, Ludovic Coutable
  • Publication number: 20120215023
    Abstract: A method for performing a chemical reaction to produce a target compound by heating a reaction medium containing a reactant in a reactor, the reaction medium being brought into contact with a solid heating medium that can be heated by electromagnetic induction and that is located inside the reactor and surrounded by the reaction medium and the heating medium being heated by electromagnetic induction with the aid of an inductor, causing the target compound to form, and the target compound being separated from the heating medium, wherein the target compound has a lower molar mass than the reactant and at least one covalent bond of the reactant is cleaved in order to produce said target compound from the reactant.
    Type: Application
    Filed: February 21, 2012
    Publication date: August 23, 2012
    Inventors: Carsten Friese, Andreas Kirschning, Sascha Volkan Ceylan, Juergen Wichelhaus
  • Publication number: 20120203021
    Abstract: The present invention relates to a method for producing cyanoacrylic acid esters. The method is based substantially on a transesterification reaction, wherein the transesterification reaction is performed in the presence of at least one transition metal catalyst that is formed by reacting at least one hydroxyl group-containing support material with at least one transition metal alkoxide.
    Type: Application
    Filed: January 3, 2012
    Publication date: August 9, 2012
    Applicant: Henkel AG & Co. KGaa
    Inventors: Carsten Friese, Andreas Kirschning, Ludovic Coutable
  • Publication number: 20120082934
    Abstract: [Problem] To reduce the time required for a film to exhibit decreased hydrophobicity after liquid immersion lithography while allowing the surface of a film to exhibit high hydrophobicity during liquid immersion lithography. [Solution] A radiation-sensitive resin composition including (A) a polymer that includes a repeating unit (a1) and a fluorine atom, and (B) a photoacid generator, the repeating unit (a1) including a group shown by any of the following formulas (1-1) to (1-3).
    Type: Application
    Filed: September 23, 2011
    Publication date: April 5, 2012
    Applicant: JSR Corporation
    Inventors: Kazuo Nakahara, Mitsuo Sato, Yusuke Asano
  • Patent number: 8129429
    Abstract: The present invention concerns methods for treating and preventing renal/kidney disease, insulin resistance/diabetes, fatty liver disease, and/or endothelial dysfunction/cardiovascular disease using synthetic triterpenoids, optionally in combination with a second treatment or prophylaxis.
    Type: Grant
    Filed: January 12, 2009
    Date of Patent: March 6, 2012
    Assignees: Reata Pharmaceuticals, Inc., Trustees of Dartmouth College
    Inventors: Michael B. Sporn, Karen T. Liby, Gordon W. Gribble, Tadashi Honda, Robert M. Kral, Colin J. Meyer
  • Patent number: 7851411
    Abstract: ?-Cyanoacrylates of the formula I, where: R1 is ORa wherein Ra is hydrogen, substituted alkyl, branched alkyl, branched alkenyl, cycloloalkyl, heterocyclyl, aryl, phenylalkyl or alkylimino; is NRbRc wherein Rb is hydrogen, alkyl which may be substituted, alkenyl, alkynyl; Rc is hydrogen, alkyl which may be substituted alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, phenylalkyl or alkylimino; or Rb and Rc form an alkandiyl-chain which may be substituted; or is SRd wherein Rd is hydrogen, alkyl which may be substituted, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, phenylalkyl or alkylimino; R2 is alkyl which may be substituted; is alkenyl or alkynyl; R3 is alkyl may be substituted; is alkenyl or alkynyl; R4 is hydrogen, halogen, cyano or alkyl; and their agriculturally useful salts, processes and intermediates for their preparation; and the use of these compounds or of compositions comprising these compounds for controlling undesirable plants are described.
    Type: Grant
    Filed: December 17, 2002
    Date of Patent: December 14, 2010
    Assignee: BASF SE
    Inventors: Peter Plath, Norbert Götz, Michael Rack, Andreas Landes, Cyrill Zagar, Matthias Witschel, Klaus Groβmann
  • Patent number: 7842832
    Abstract: ?-Amino-?-Cyanoacrylates of formula I where the variables have the following meanings: R1 is n-alkyl, n-alkenyl or alkoxyalkyl; R2,R3 are alkyl, which may be partially or fully halogenated and/or may carry a substituent from the group consisting of cyano, alkoxy, haloalkoxy, alkylthio, haloalkylthio, C1-C6-alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl and haloalkylsulfonyl, are alkenyl or alkynyl; or R2 and R3 together with the carbon atom to which they are attached form a cycloalkyl ring in which one or two nonadjacent CH2 groups may be replaced by oxygen or sulfur, and where the cycloalkyl ring may be substituted by halogen or alkyl; R4 is hydrogen, halogen, cyano or alkyl, where the substituents R2, R3 and R4 or two of the radicals R2, R3 and R4 are not simultaneously methyl, and their agriculturally useful salts, processes and intermediates for their preparation; and the use of these compounds or of compositions comprising these compounds for controlling undesirable plants are described.
    Type: Grant
    Filed: December 17, 2002
    Date of Patent: November 30, 2010
    Assignee: BASF SE
    Inventors: Albert C. Everson, Daniel J. Coughlin, Michael A. Guaciaro, Linda B. Fleming, Lester L. Maravetz, John L. Huppatz
  • Publication number: 20100210788
    Abstract: This invention relates to novel electron deficient olefins, such as certain 2-cyanoacrylates and methylidene malonates, prepared using an imine or an iminium salt.
    Type: Application
    Filed: April 23, 2010
    Publication date: August 19, 2010
    Applicant: Loctite (R&D) Limited
    Inventors: Ciaran B. McArdle, Ligang Zhao, Stefano Gherardi, Kevin Murnaghan
  • Publication number: 20100199888
    Abstract: This invention relates to novel compounds with ester linkage(s) capped with either electron deficient olefinic linkage(s) or group(s) or reactive functional groups (termed herein as “active methylene reagents”), and curable compositions prepared therefrom.
    Type: Application
    Filed: April 23, 2010
    Publication date: August 12, 2010
    Applicant: Loctite (R&D) Limited
    Inventors: Ciaran B. McArdle, Ligang Zhao, Stefano Gherardi, Kevin Murnaghan
  • Patent number: 7718821
    Abstract: This invention relates to a process for producing electron deficient olefins, such as 2-cyanoacrylates, using an iminium salt.
    Type: Grant
    Filed: December 19, 2006
    Date of Patent: May 18, 2010
    Assignees: Loctite (R&D) Limited, Universita Degli Studi di Parma
    Inventors: Franca Bigi, Stefano Gheradi, Ciaran B. McArdle
  • Patent number: 7709676
    Abstract: A method for producing a purified 2-cyanoacrylate is characterized in that distillation is conducted in the presence of a polymerization inhibitor whose boiling point is within ±12° C. of the boiling point of the 2-cyanoacrylate. With this method, polymerization of 2-cyanoacrylate can be continuously prevented in the distillate system during distillation of a crude 2-cyanoacrylate, so that a purified 2-cyanoacrylate can be obtained.
    Type: Grant
    Filed: May 27, 2004
    Date of Patent: May 4, 2010
    Assignee: Toagosei Co., Ltd.
    Inventors: Muneaki Kanou, Yoshiharu Ohashi
  • Patent number: 7659423
    Abstract: This invention relates to a process for producing electron deficient olefins, such as 2-cyanoacrylates, in a polar solvent, such as an ionic liquid.
    Type: Grant
    Filed: April 18, 2006
    Date of Patent: February 9, 2010
    Assignee: Loctite (R&D) Limited
    Inventor: Ciaran B. McArdle
  • Publication number: 20090317529
    Abstract: Aromachemical compounds of Formula I, compositions comprising these compounds and processes for their preparation are disclosed, wherein R1 is H, C(O)O—CH2—CH3; C(O)O—CH3, or C(O)O—H; R2 is methyl; R3 and R4 are H; R5 and R6 are CH3; Z is C(H)2; and X is —CN. The double bond attached to X can be in the E or Z configuration.
    Type: Application
    Filed: June 15, 2009
    Publication date: December 24, 2009
    Applicant: Flexitral, Inc.
    Inventor: Luca Turin
  • Patent number: 7622603
    Abstract: Disclosed is a process for producing a ?-aminopentadienoate compound represented by the following formula (I), the process including reacting a ?-aminopentadienoate compound represented by the following formula (II) with an alcohol represented by the following formula (III): wherein in formulae (I to III) R11 and R21 each independently represent an aliphatic group, an aromatic group, or a heterocyclic group bonded via a carbon atom; R12 to R16 each independently represent a hydrogen atom, an aliphatic group, an aromatic group, or a heterocyclic group bonded via a carbon atom; Y11 represents an electron-withdrawing group; and R11 and R21 are not the same group.
    Type: Grant
    Filed: September 27, 2007
    Date of Patent: November 24, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Keizo Kimura
  • Publication number: 20090264657
    Abstract: Described is the use of specific merocyanine derivatives for protecting body-care and household products from photolytic and oxidative degradation. These compounds perform outstanding UV absorber properties.
    Type: Application
    Filed: July 19, 2006
    Publication date: October 22, 2009
    Inventors: Barbara Wagner, Oliver Reich
  • Patent number: 6730803
    Abstract: The &bgr;-keto ester compound, &bgr;-hydroxy acid compound and acetonide form of a 1,3-diol derivative of the formulas (I), (V) and (VIII) wherein each symbol is as defined in the specification, are useful as a synthetic intermediate for an epothilone derivative being developed as a pharmaceutical agent having an antitumor activity.
    Type: Grant
    Filed: September 30, 2002
    Date of Patent: May 4, 2004
    Assignee: Sumika Fine Chemicals Co., Ltd.
    Inventors: Mitsuhiro Iwasaki, Kiyoshi Sugi, Hideto Miyamoto, Nobushige Itaya
  • Patent number: 6700010
    Abstract: A method for producing cyanoacetic acid esters of general formula (I): wherein R represents on optionally substituted linear or branched C1-8 alkyl group or an aryl C1-4 alkyl group. According to the method, an alkoxypropionitrile of the general formula (II): wherein R is defined above, is oxidized to form the desired product in the presence of a catalyst, based on lead or on one of the transition metals, using oxygen or an oxygen-forming reagent.
    Type: Grant
    Filed: July 12, 2002
    Date of Patent: March 2, 2004
    Assignee: Lonza AG
    Inventors: Paul Hanselmann, Stefan Hildbrand
  • Patent number: 6420590
    Abstract: Continuous processes for forming cyanoacrylate from polycyanoacrylate include stripping a solvent from a reaction mass; cracking a polymer in the reaction mass to form a cracked cyanoacrylate monomer and residue substances; and distilling the cracked cyanoacrylate monomer to produce a cyanoacrylate monomer product. These steps can be performed in short-path, wiped-film evaporators. Polycyanoacrylate used in the processes can be formed using cyanoacetate produced by processes for continuously producing cyanoacetate by forming a higher homologue cyanoacetate from a lower homologue cyanoacetate. The cyanoacetate can be formed in short-path, wiped-film evaporators.
    Type: Grant
    Filed: October 31, 2000
    Date of Patent: July 16, 2002
    Assignee: Closure Medical Corporation
    Inventors: Ibraheem T. Badejo, Jaime Ayarza, Kenneth W. Davis, Jeffrey R. Hennenkamp
  • Publication number: 20010016665
    Abstract: A method of making (±)-3-(aminomethyl)-5-methylhexanoic acid that comprises condensing isovaleraldehyde with 1
    Type: Application
    Filed: October 5, 1999
    Publication date: August 23, 2001
    Inventors: TODD MICHEL GROTE, BRIAN KEITH HUCKABEE, THOMAS MULHERN, DENIS MARTIN SOBIERAY, ROBERT DANIEL TITUS
  • Patent number: 6271410
    Abstract: C3-12 alkyl, substituted alkyl, alkenyl and cycloalkyl cyanoacetates are prepared by an efficient and simplified one-step process in which a small molar excess of the corresponding alcohol, i.e., C3-12 alkyl, substituted alkyl, alkenyl or cycloalkenyl alcohol is reacted with crystalline cyanoacetic acid, or a concentrated aqueous solution of cyanoacetic acid, in the presence of an acid catalyst, such as, for example, methanesulfonic acid, p-toluenesulfonic acid, sulfuric acid and phosphoric acid at a temperature in the range of from about 60° C. to about 150° C., in accordance with the following reaction: CNCH2COOH+R—OH→(cat)CNCH2COOR+H2O  (I) where R is a C3-12 alkyl, substituted alkyl, alkenyl or cycloalkyl.
    Type: Grant
    Filed: June 6, 2000
    Date of Patent: August 7, 2001
    Assignee: Creanova Inc.
    Inventors: Thomas V. John, Chitoor S. Subramaniam, Mark Whipkey
  • Patent number: 6245933
    Abstract: An &agr;-cyanoacrylate may be formed by first condensing a cyanoacetate with paraformaldehyde or formaldehyde; reacting the polymer formed with an alcohol to transesterify the polymer; and depolymerizing the polymer to form &agr;-cyanoacrylate monomers.
    Type: Grant
    Filed: November 19, 1999
    Date of Patent: June 12, 2001
    Assignee: Closure Medical Corporation
    Inventors: Bernard Malofsky, Ibraheem T. Badejo
  • Patent number: 6239307
    Abstract: Cyanoacetic esters of the general formula: in which R is C1-10-alkyl, C3-10-alkenyl or aryl-C1-4alkyl, are prepared by the reaction of alkali metal cyanoacetates with the corresponding halides R—X, in which X is chlorine, bromine or iodine, in an aqueous/organic two-phase system in the presence of a phase-transfer catalyst.
    Type: Grant
    Filed: February 9, 2000
    Date of Patent: May 29, 2001
    Assignee: Lonza AG
    Inventors: Stefan Hildbrand, Paul Hanselmann
  • Patent number: 6191202
    Abstract: Alkyl cyanoacrylate compositions comprising at least one alkyl cyanoacrylate, a biocompatible plasticizer (preferably an acyl trialkyl citrate wherein the acyl group contains from 2 to 4 carbon atoms and each alkyl group contains from 4 to 6 carbon atoms), and SO2 as an anionic polymerization inhibitor are provided. These compositions are suitable for topical application to human skin.
    Type: Grant
    Filed: July 3, 1997
    Date of Patent: February 20, 2001
    Assignee: Medlogic Global Corporation
    Inventors: Richard J. Greff, Patrick J. Tighe, Michael M. Byram, Leonard V. Barley
  • Patent number: 6191301
    Abstract: Use of 4,4-diarylbutadienes of the formula I, where the variables have the meanings explained in the description, as water-soluble photostable UV filters in cosmetic and pharmaceutical preparations for protecting the human skin or human hair from the sun's rays, alone or together with compounds which absorb in the UV region and are known per se for cosmetic and pharmaceutical preparations.
    Type: Grant
    Filed: March 16, 2000
    Date of Patent: February 20, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Thorsten Habeck, Horst Westenfelder, Thomas Wünsch
  • Patent number: 5998472
    Abstract: Disclosed are mixed alkyl cyanoacrylate compositions which are specifically formulated for topical application onto intact or broken human skin, preferably without the addition of a plasticizing agent to the composition.
    Type: Grant
    Filed: October 9, 1998
    Date of Patent: December 7, 1999
    Assignee: MedLogic Global Corporation
    Inventors: Thomas Jay Berger, Carlos Roberto Morales, Richard J. Greff, Ian N. Askill
  • Patent number: 5908954
    Abstract: A process for the preparation of five-membered or six-membered ring lactams from aliphatic .alpha.,.omega.-dinitriles has been developed. In the process an aliphatic .alpha.,.omega.-dinitrile is first converted to an ammonium salt of an .omega.-nitrile-carboxylic acid in aqueous solution using a catalyst having an aliphatic nitrilase (EC 3.5.5.7) activity, or a combination of nitrile hydratase (EC 4.2.1.84) and arnidase (EC 3.5.1.4) activities. The ammonium salt of the .omega.-nitrilecarboxylic acid is then converted directly to the corresponding lactam by hydrogenation in aqueous solution, without isolation of the intermediate .omega.-nitrilecarboxylic acid or .omega.-aminocarboxylic acid. When the aliphatic .alpha.,.omega.-dinitrile is also unsymmetrically substituted at the .alpha.-carbon atom, the nitrilase produces the .omega.-nitrilecarboxylic acid ammonium salt resulting from hydrolysis of the .omega.
    Type: Grant
    Filed: July 1, 1998
    Date of Patent: June 1, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Robert Di Cosimo, Robert Donald Fallon, John Edward Gavagan, Frank Edward Herkes
  • Patent number: 5861533
    Abstract: A process for nitrosating C-H-acidic compounds. The process substantially avoids producing polluted wastewater.
    Type: Grant
    Filed: June 5, 1997
    Date of Patent: January 19, 1999
    Assignee: Huels Aktiengesellschaft
    Inventors: Frank Bauer, Marcel Feld
  • Patent number: 5856521
    Abstract: A monomer of the formula: ##STR1## wherein R5, R6 and R7 are independently hydrogen, alkyl, cyano, alkyloxycarbonyl or carbamoyl; Z is a spacer or a direct link; and R is hydroxyalkyl having a protected terminal hydroxy, can produce a polymer useful for producting a resist composition.
    Type: Grant
    Filed: April 28, 1998
    Date of Patent: January 5, 1999
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Motoshige Sumino, Kazuhito Fukasawa
  • Patent number: 5821380
    Abstract: Novel 2-cyanoacrylic esters I ##STR1## where the radicals have the following meanings: R.sup.1 and R.sup.2 are each hydrogen or a radical having an iso- or heterocyclic ring system with at least one iso- or heteroaromatic nucleus, and at least one of the radicals R.sup.1 or R.sup.2 must be different from hydrogen,n is from 2 to 10, andX is, when n=2, a radical of the formula II ##STR2## where m is from 2 to 8, and X is, when n>2, the radical of an n-hydric aliphatic or cycloaliphatic polyol having 3-20 carbon atoms, it also being possible for a cycloaliphatic radical to contain 1 or 2 hetero atoms, and for an aliphatic radical to be interrupted by up to 8 non-adjacent oxygen atoms, sulfur atoms, imino or C.sub.1 -C.sub.4 -alkylimino groups, are used as light stabilizers.
    Type: Grant
    Filed: May 12, 1997
    Date of Patent: October 13, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Holderbaum, Alexander Aumuller, Hubert Trauth, Guido Voit, Karin Sperling, Alfred Krause
  • Patent number: 5762919
    Abstract: Disclosed are cyanoacrylate compositions comprising a compatible antimicrobial agent and, in particular, a compatible iodine containing antimicrobial agent. These compositions provide for in situ formation of an antimicrobial polymeric cyanoacrylate film on mammalian skin.
    Type: Grant
    Filed: June 6, 1997
    Date of Patent: June 9, 1998
    Assignee: Medlogic Global Corporation
    Inventors: Richard J. Greff, Michael M. Byram
  • Patent number: 5756807
    Abstract: A process for preparing alkyl cyanoacetates of the general formula I ##STR1## where R is an n-valent aliphatic radical which has 6 to 20 carbon atoms and whose carbon framework can be interrupted by one to three oxygen atoms in ether functionality, and n is a number from 1 to 6, by reacting cyanoacetic acid in aqueous medium with an alcohol R(OH).sub.n, where the esterification is carried out in the presence of an inert entrainer and, during the reaction, water and entrainer are distilled out.
    Type: Grant
    Filed: October 21, 1996
    Date of Patent: May 26, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Clemens Grund, Martin Holderbaum, Helmut Reichelt, Stefan Beckmann
  • Patent number: 5753699
    Abstract: Antimicrobial cyanoacrylate compositions are applied to non-suturable, superficial wound surfaces. In situ polymerization of the cyanoacrylate ester provides for a polymeric film over the wound which promotes wound healing and retards infection of the wound.
    Type: Grant
    Filed: October 9, 1997
    Date of Patent: May 19, 1998
    Assignee: MedLogic Global Corporation
    Inventors: Richard J. Greff, Michael M. Byram
  • Patent number: 5726342
    Abstract: There is provide an advantageous process for producing an .alpha.-(tert-alkyl)cyanoacetic acid ester characterized by reacting cyanoacetic acid ester with a di(lower alkyl)aluminum halide, and then reacting the resulting reaction with a tert-alkyl halide.
    Type: Grant
    Filed: January 22, 1997
    Date of Patent: March 10, 1998
    Assignee: Sumitomo Chemical Limited, Company
    Inventors: Atsushi Kaetsu, Yoshimi Yamada
  • Patent number: 5698730
    Abstract: A cyanoacetic acid higher ester represented by the general formula: NCCH.sub.2 COOR', wherein R' represents an alkyl group having 4 to 20 carbon atoms, is prepared by subjecting a cyanoacetic acid ester represented by the general formula: NCCH.sub.2 COOR.sup.1, wherein R.sup.1 represents an alkyl group having 1 to 3 carbon atom, to a transesterification with an alcohol represented by the general formula: R'OH, wherein R' represents an alkyl group having 4 to 20 carbon atoms, in the presence of a specific tin compound as the catalyst. According to the present invention, the cyanoacetic acid higher esters which are useful as intermediates for pharmaceuticals and agricultural chemicals as well as intermediates for industrial products can be prepared easily and in higher yield as compared with conventional methods, by using a cyanoacetic acid ester and an alcohol which are less expensive and easily available as raw materials.
    Type: Grant
    Filed: December 18, 1996
    Date of Patent: December 16, 1997
    Assignee: Nitto Chemical Industry Co., Ltd.
    Inventors: Katsumi Nakamura, Yasuyuki Takayanagi, Masaaki Seya
  • Patent number: 5684042
    Abstract: Disclosed are cyanoacrylate compositions comprising a compatible antimicrobial agent and, in particular, a compatible iodine containing antimicrobial agent. These compositions provide for in situ formation of an antimicrobial polymeric cyanoacrylate film on mammalian skin.
    Type: Grant
    Filed: January 10, 1997
    Date of Patent: November 4, 1997
    Assignee: Medlogic Global Corporation
    Inventors: Richard J. Greff, Michael M. Byram