Azines (i.e., Hch=n-n=hch, Wherein Substitution May Be Made For Hydrogen) Patents (Class 564/249)
  • Patent number: 8871977
    Abstract: Disclosed are a novel asymmetric azine compound (I) and a method for producing an asymmetric azine compound (I) which is characterized in that an aldehyde compound (III) and hydrazine are reacted in an alcohol solvent at a molar ratio (aldehyde compound (III)):(hydrazine) of from 2:1 to 1:2, thereby obtaining a reaction solution including a hydrazone compound (IV), and then an aldehyde compound (V) is added for a reaction into the thus-obtained reaction solution at a molar ratio (aldehyde compound (V)):(hydrazone compound (IV)) of from 2:1 to 1:2. The method can commercially advantageously produce an asymmetric azine compound having a polar group such as a hydroxyl group or a carboxyl group in each molecule. The novel asymmetric azine compound can be obtained by this production method. (In the formulae, R1 and R2 each represents a hydroxyl group or a carboxyl group, X1 to X8 each represents a hydrogen atom, —C(?O)—OR3 or the like; and R3 represents an alkyl group having 1 to 10 carbon atoms or the like.
    Type: Grant
    Filed: June 17, 2009
    Date of Patent: October 28, 2014
    Assignee: Zeon Corporation
    Inventors: Kei Sakamoto, Yasushi Nakano
  • Patent number: 8362273
    Abstract: Process for preparing aminale and their use for preparing 1,3-disubstituted pyrazole compounds.
    Type: Grant
    Filed: October 28, 2010
    Date of Patent: January 29, 2013
    Assignee: BASF SE
    Inventors: Maximilian Dochnahl, Michael Keil, Roland Goetz
  • Publication number: 20120215009
    Abstract: Process for preparing aminale and their use for preparing 1,3-disubstituted pyrazole compounds.
    Type: Application
    Filed: October 28, 2010
    Publication date: August 23, 2012
    Applicant: BASF SE
    Inventors: Maximilian Dochnahl, Michael Keil, Roland Goetz
  • Patent number: 8158021
    Abstract: A polymerizable liquid crystal compound shown by the following formula (I), a polymerizable liquid crystal composition that includes the polymerizable liquid crystal compound and a chiral compound polymerizable with the polymerizable liquid crystal compound, a liquid crystalline polymer obtained by polymerizing the polymerizable liquid crystal compound or the polymerizable liquid crystal composition, and an optical anisotropic article that includes the liquid crystalline polymer. The polymerizable liquid crystal compound shows a liquid crystal phase over a wider temperature range, is chemically stable, can be inexpensively produced, and has a wide selective reflection wavelength band ?? (i.e., a large value ?n).
    Type: Grant
    Filed: April 24, 2008
    Date of Patent: April 17, 2012
    Assignee: Zeon Corporation
    Inventors: Kei Sakamoto, Naoto Kogoshi, Yoshihide Yachi
  • Publication number: 20110144379
    Abstract: Disclosed are a novel asymmetric azine compound (I) and a method for producing an asymmetric azine compound (I) which is characterized in that an aldehyde compound (III) and hydrazine are reacted in an alcohol solvent at a molar ratio (aldehyde compound (III)):(hydrazine) of from 2:1 to 1:2, thereby obtaining a reaction solution including a hydrazone compound (IV), and then an aldehyde compound (V) is added for a reaction into the thus-obtained reaction solution at a molar ratio (aldehyde compound (V)):(hydrazone compound (IV)) of from 2:1 to 1:2. The method can commercially advantageously produce an asymmetric azine compound having a polar group such as a hydroxyl group or a carboxyl group in each molecule. The novel asymmetric azine compound can be obtained by this production method. (In the formulae, R1 and R2 each represents a hydroxyl group or a carboxyl group, X1 to X8 each represents a hydrogen atom, —C(?O)—OR3 or the like; and R3 represents an alkyl group having 1 to 10 carbon atoms or the like.
    Type: Application
    Filed: June 17, 2009
    Publication date: June 16, 2011
    Applicant: ZEON CORPORATION
    Inventors: Kei Sakamoto, Yasushi Nakano
  • Patent number: 7932422
    Abstract: The invention relates to chlorine Guanabenz derivatives for treating Huntington's disease and other polyglutamine expansion associated diseases. More specifically, it relates to the use of the molecule of formula (I) wherein R?H or Cl and the phenyl group is at least substituted twice, or a pharmaceutically acceptable salt thereof, for the manufacture of a medicament for treating polyglutamine expansion associated diseases.
    Type: Grant
    Filed: October 3, 2007
    Date of Patent: April 26, 2011
    Inventors: Anne Bertolotti, Marc Blondel
  • Patent number: 7812113
    Abstract: A monomer with a chromophore group represented by Formula (I): wherein AR1 represents a substituted or unsubstituted aromatic group; AR2 represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted alkyl group; and R represents a substituted or unsubstituted alkyl group, with the proviso that one of R, AR1, and AR2 has a substituent with a polymerizable functional group. The monomer can be advantageously used to prepare polymeric dispersants for pigment dispersion, especially inkjet inks.
    Type: Grant
    Filed: July 4, 2006
    Date of Patent: October 12, 2010
    Assignee: Agfa Graphics NV
    Inventors: Geert Deroover, Wojciech Jaunky, Lambertus Groenendaal, Johan Loccufier
  • Publication number: 20100105950
    Abstract: A process for preparing a ketazine compound of the formula (1) from a ketone compound of the formula (2), ammonia and an oxidizing agent, wherein a solution containing the ketone compound of the formula (2) and ammonia is brought into contact with an aqueous solution of the oxidizing agent in a tubular reactor having a flow channel width of 2 to 10000 ?m wherein R1 and R2 are the same or different and are each a C1-6 alkyl group, or R1 and R2 are combined with each other into a straight-chain C2-7 alkylene group wherein R1 and R2 are the same as above.
    Type: Application
    Filed: February 14, 2008
    Publication date: April 29, 2010
    Inventors: Masatoshi Taniguchi, Koji Mori
  • Patent number: 7501216
    Abstract: This invention includes an improved organophotoreceptor having an electrically conductive substrate and a photoconductive element on the electrically conductive substrate where the photoconductive element comprises: (a) a charge transport material having the formula Y?N—N?X?N—N?Y? where Y and Y? comprise, each independently, a 9-fluorenylidene group; and X is a conjugated linking group that allows the delocalization of pi electrons over at least Y and Y?, such as a 1,2-ethanediylidene group, a 1,4-phenylenedimethylidyne group, a 2,4-cyclohexadienylidene group, a 2,5-cyclohexadienylidene group, a bicyclohexylidene-2,5,2?,5?-tetraene group, a bicyclohexylidene-2,4,2?,4?-tetraene group, or a combination thereof; and (b) a charge generating compound. Corresponding electrophotographic apparatuses and imaging methods are described.
    Type: Grant
    Filed: March 19, 2004
    Date of Patent: March 10, 2009
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Nusrallah Jubran, Zbigniew Tokarski, Kam W. Law
  • Patent number: 7488353
    Abstract: Cationic heteroarylazine dyes of general formulas (I) and (II) and colorants for keratin fibers containing these compounds.
    Type: Grant
    Filed: December 2, 2004
    Date of Patent: February 10, 2009
    Assignee: Wella AG
    Inventors: Markus Speckbacher, Hans-Juergen Braun
  • Patent number: 7439396
    Abstract: Novel ligand compounds that activate RAR receptors have the following structural formula (I): and are suited for formulation into pharmaceutical compositions useful in human or veterinary medicine, or, alternatively, into cosmetic compositions.
    Type: Grant
    Filed: April 14, 2006
    Date of Patent: October 21, 2008
    Assignee: Galderma Research & Development
    Inventors: Thibaud Biadatti, Anne-Pascale Luzy
  • Patent number: 7316877
    Abstract: Improved organophotoreceptor comprises an electrically conductive substrate and a photoconductive element on the electrically conductive substrate, the photoconductive element comprising: (c) a charge transport material having the formula: R1—N?N—Ar1—X—Ar2—N?N—R2 where R1 and R2 comprise, each independently, a 4-oxo-2,5-cyclohexadiene-1-ylidenyl group; X comprises oxy, thio, sulfonyl, sulfinyl, sulfonyldioxy, azo, carbonyl, thiocarbonyl, carbonyldioxy, oxalyl, an arylene group, an arylenebisazo group, an imino group, a hydrazo group, a carbonimidoyl group, a vinylene group, or a combination thereof; and Ar1 and Ar2 comprise, each independently, an aromatic group; and (b) a charge generating compound. Corresponding electrophotographic apparatuses, imaging methods, and the charge transport material are also described.
    Type: Grant
    Filed: October 29, 2004
    Date of Patent: January 8, 2008
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Nusrallah Jubran, Patrick Knoll
  • Patent number: 7300732
    Abstract: Improved organophotoreceptor comprises an electrically conductive substrate and a photoconductive element on the electrically conductive substrate, the photoconductive element comprising: (a) a charge transport material having the formula, where R comprises a hydrogen, an alkyl group, an alkenyl group, a heterocyclic group, or an aromatic group; X comprises an arylamine group; and Y comprises a 9-fluorenylidene group having at least a solubilizing substituent; and (b) a charge generating compound. Corresponding electrophotographic apparatuses and imaging methods are described.
    Type: Grant
    Filed: February 10, 2004
    Date of Patent: November 27, 2007
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Nusrallah Jubran, Zbigniew Tokarski, Kam W. Law
  • Patent number: 7261988
    Abstract: An improved organophotoreceptor comprises an electrically conductive substrate and a photoconductive element on the electrically conductive substrate, the photoconductive element comprising: (a) a charge transport material having the formula where X comprises a linking group; R1 and R1? comprise, each independently, H, an alkyl group, an alkenyl group, an alkynyl group, an aromatic group, or a heterocyclic group; and R2, R3, R2?, and R3? comprise, each independently, an arylamine group; and (b) a charge generating compound. Corresponding electrophotographic apparatuses, imaging methods, and methods of forming the charge transport material are described.
    Type: Grant
    Filed: April 27, 2004
    Date of Patent: August 28, 2007
    Assignee: Samsung Electronics Co. Ltd
    Inventors: Zbigniew Tokarski, Nusrallah Jubran, Vytautas Getautis, Maryte Daskeviciene, Ingrida Paulauskaite, Robertas Maldzius, Jonas Sidaravicius
  • Patent number: 7115347
    Abstract: Improved organophotoreceptor comprises an electrically conductive substrate and a photoconductive element on the electrically conductive substrate, the photoconductive element comprising: (a) a charge transport material having the formula where R1, R2, R3, and R4 comprise, each independently, an alkyl group, an alkenyl group, an aromatic group, a heterocyclic group, or a part of a ring group; X and X? comprise, each independently, an aromatic group; Y and Y? comprise, each independently, a (disubstituted)methylene group; and Z is a linking group; (b) a charge generating compound; and (c) an electrically conductive substrate on which said charge transport material and said charge generating compound are located. Corresponding electrophotographic apparatuses and imaging methods are also described.
    Type: Grant
    Filed: January 16, 2004
    Date of Patent: October 3, 2006
    Assignee: Samsung Electronics Co., LTD
    Inventors: Zbigniew Tokarski, Nusrallah Jubran, Vytautas Getautis, Valentas Gaidelis, Maryte Daskeviciene, Edmundas Montrimas, Ingrida Paulauskaite, Jonas Sidaravicius
  • Patent number: 7034184
    Abstract: A process comprising allowing a peroxide compound represented by following Formula (2): wherein Ra, Rb, Rc and Rd are the same or different and are each a hydrogen atom or a hydrocarbon group, and wherein Ra and Rb, Rc and Rd may be combined to form a ring together with the adjacent carbon atom, respectively, to react with ammonia and water to yield an azine compound represented by following Formula (3): wherein Ra, Rb, Rc and Rd have the same meanings as defined above, or oxime compounds represented by following Formulae (4a) and/or (4b): wherein Ra, Rb, Rc and Rd have the same meanings as defined above, in the presence of a nitrogen-containing cyclic compound constitutively having a skeleton represented by following Formula (A) in its ring: wherein X is one of an oxygen atom and an —OR group, and wherein R is one of a hydrogen atom and a hydroxyl-protecting group.
    Type: Grant
    Filed: March 6, 2003
    Date of Patent: April 25, 2006
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yasutaka Ishii, Tatsuya Nakano
  • Patent number: 6818794
    Abstract: Process for extracting aqueous ketazine solutions which is carried out using an aqueous ketazine solution having a salt content of 5 to 27% by weight and an ammonia content of 0 to 28% by weight to extract at temperatures of 50 to 120° C., which is characterized in that the ketazine solution to be extracted has a molar excess of 50 to 200% of ketone based on the ketazine to be extracted, and that an aliphatic hydrocarbon extractant is used which has a boiling point of 150 to 300° C. at atmospheric pressure.
    Type: Grant
    Filed: November 27, 2002
    Date of Patent: November 16, 2004
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ottfried Schlak, Hans-Georg Adams, Johannes Kaulen
  • Publication number: 20040147746
    Abstract: This invention provides compounds and methods for treating melanocortin receptor associated disorders, such as weight loss disorders including cachexia resulting from cancer and other chronic illnesses.
    Type: Application
    Filed: December 4, 2003
    Publication date: July 29, 2004
    Applicant: Millennium Pharmaceuticals, Inc.
    Inventors: Tricia J. Vos, Michael Patane, Michael E. Solomon, Christopher Blackburn, Mihaela D. Danca
  • Patent number: 6605265
    Abstract: Azines, e.g., ketazines, are continuously produced by (i) establishing a loop having an azine reaction medium circulating therein, such loop including an azine reaction zone, means for separating azine final product from the circulating reaction medium, means for heating the reaction medium and for purging water therefrom, and means for recycling heated and purged reaction medium to the azine reaction zone, (ii) introducing hydrogen peroxide, ammonia and a carbonyl compound into the circulating reaction medium in the azine reaction zone, (iii) withdrawing azine final product thus formed from the circulating reaction medium. downstream of the azine reaction zone, (iii) thereafter purging water from the circulating reaction medium to maintain the volume thereof essentially constant, (iv) heating the circulating reaction medium to a temperature of at least 130° C.
    Type: Grant
    Filed: March 25, 1994
    Date of Patent: August 12, 2003
    Assignee: Atochem
    Inventors: Jean-Pierre Schirmann, Jean-Pierre Pleuvry, Pierre Tellier
  • Patent number: 6562311
    Abstract: The invention concerns a method for preparing methyl ethyl ketone azine which consists in: (a) reacting ammonia, hydrogen peroxide and methyl ethyl ketone in the presence of a working solution to form an azine; (b) separating the working solution and the azine possibly containing methyl ethyl ketone which has not reacted and butanol-2; (c) recycling the working solution to step (a) after optional treatment; (d) separating the methyl ethyl ketone and the butanol-2 from the azine. The butanol-2 of the flow in step (d) is either purged or dehydrogenated in MEK and recycled at step (a).
    Type: Grant
    Filed: January 25, 2001
    Date of Patent: May 13, 2003
    Assignee: Atofina
    Inventors: Jean-Pierre Schirmann, Paul Bourdauducq
  • Patent number: 6551568
    Abstract: Process for the preparation of azine and of hydrazine by bringing ammonia, hydrogen peroxide and a reactant carrying a carbonyl group into contact with a working solution, comprising: the treatment of an aqueous stream resulting from the circuit for the regeneration of the said working solution with an amount of acid such that the pH of the said stream is brought to a value of less than 6.4, then the recycling of the said stream in the reactor for the synthesis of the azine.
    Type: Grant
    Filed: April 5, 2001
    Date of Patent: April 22, 2003
    Assignee: Atofina
    Inventors: Georges Brenguer, Rémi Jullin, Jean-Philippe Ricard
  • Patent number: 6410600
    Abstract: The invention relates to novel azines, to a process for their preparation and to their use as fungicides.
    Type: Grant
    Filed: October 19, 2000
    Date of Patent: June 25, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dirk Backhaus, Bernd-Wieland Krüger, Peter Gerdes, Herbert Gayer, Martin Vaupel, Klaus Stenzel
  • Patent number: 6265613
    Abstract: Phenylacetic acid derivatives of the formula I where the substituents and the indexes have the meanings given in the specification, their salts, their preparation and their use.
    Type: Grant
    Filed: February 24, 1998
    Date of Patent: July 24, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Müller, Hubert Sauter, Herbert Bayer, Wassilios Grammenos, Thomas Grote, Reinhard Kirstgen, Klaus Oberdorf, Franz Röhl, Norbert Götz, Michael Rack, Ruth Müller, Gisela Lorenz, Eberhard Ammermann, Siegfried Strathmann, Volker Harries
  • Patent number: 6229047
    Abstract: A nonlinear optical material which is characterized as having a relatively high macroscopic dipole moment achieved through the generally parallel packing of dipolar molecules in a relative orientation to reinforce their dipole moments. The nonlinear optical material may be a crystalline azine or imine bridged di-arene in which the arenyl groups, which can be the same or different, are substituted with an electron donor group on the first arenyl group Ar1 and A is an electron acceptor group which is substituted on the second arenyl group Ar2. B is an azine or imine bridge which extends between and interconnects the first and second arenyl groups. The nonlinear optical material has a dipole alignment factor of at least 0.1, more preferably, at least 0.5.
    Type: Grant
    Filed: December 4, 1995
    Date of Patent: May 8, 2001
    Assignee: The Curators of the University of Missouri
    Inventors: Ranier E. Glaser, Grace S. Chen
  • Patent number: 6010642
    Abstract: Disclosed is to provide an azine derivative as a novel liquid crystal compound, a novel process for the preparation of an asymmetrical azine in a high reaction yield with an extremely small amount of by-products such as symmetrical azines, a nematic liquid crystal composition containing the azine derivative which exhibits a broad driving temperature range and an excellent response for the desired high birefringence index, a liquid crystal display device such as TN-LCD, STN-LCD and TFT-LCD having improved electro-optical properties comprising the liquid crystal composition as a constituent material, and a light-scattering type liquid crystal display system which exhibits a suppressed memory phenomenon, a higher uniformity in turbidity for display and improved display properties and response against temperature change while maintaining and improving the required display properties such as fast switching time, lower voltage driving, higher light-control layer resistivity and higher contrast ratio even in the for
    Type: Grant
    Filed: August 21, 1997
    Date of Patent: January 4, 2000
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Haruyoshi Takatsu, Sadao Takehara, Kiyofumi Takeuchi, Makoto Negishi, Norie Osawa, Masashi Osawa, Shinji Ogawa, Hirokazu Yanagihara
  • Patent number: 5986134
    Abstract: A process for continuously and stably synthesizing a ketazine from hydrogen peroxide, ammonia and methyl ethyl ketone in the presence of a solution containing a catalyst. The process comprises removing sec-butyl alcohol by distillation from methyl ethyl ketone, which is reused by circulation. Also a process for preparing a hydrazine hydrate which comprises hydrolyzing the ketazine. By circulating unreacted ketone, accumulation of impurities in the circulated ketone can be prevented to obtain a high yield of the ketazine and the hydrazine hydrate, for a long period of time.
    Type: Grant
    Filed: July 19, 1996
    Date of Patent: November 16, 1999
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Yasuhisa Kuriyama, Nobuhiro Nagata, Kiyoshi Yoshida
  • Patent number: 5612479
    Abstract: Novel polycyanate compositions containing one or more mesogenic moieties as lateral substituents are disclosed which provide improved processability relative to polycyanates containing one or more mesogenic moieties in the main chain of the molecule. Molecular level ordering of the resulting thermosets is maintained much similar to that found thermosets of polycyanates which have one or more mesogenic moieties in the main chain.
    Type: Grant
    Filed: August 17, 1994
    Date of Patent: March 18, 1997
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5600001
    Abstract: Azines of formula (I): ##STR1## in which R and R' either are identical and represent an alkyl radical containing 1 to 4 carbon atoms or an alkenyl radical containing 3 to 5 carbon atoms, or together form a radical of formula (II):--CHR.sub.1 --(CR.sub.2 R.sub.3).sub.n --CHR.sub.4 -- (II)in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4, identical or different, represent a hydrogen atom or an alkyl radical containing 1 to 4 carbon atoms and n represents 0 or 1, in their different stereoisomer forms, their preparation process and their use.
    Type: Grant
    Filed: February 22, 1996
    Date of Patent: February 4, 1997
    Assignee: Societe Francaise Hoechst
    Inventors: Alain Schouteeten, Yani Christidis
  • Patent number: 5543433
    Abstract: Compounds of the formula I ##STR1## where X is hydrogen, halogen, alkyl, alkoxy, trifluoromethyl, cyano or nitro,Y is an amino, methylamino or dimethylamino group,Z is a group CHCH.sub.3, CHOCH.sub.3 or NOCH.sub.3,R is hydrogen or alkyl,A is hydrogen, alkyl, haloalkyl or cycloalkyl,B is unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl or the group ##STR2## where W is hydrogen, alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, unsubstituted or substituted aryl or heteroaryl, unsubstituted or substituted aryloxy, arylthio, arylamino or aryl-N-(C.sub.1 -C.sub.6 -alkyl)amino, heteroaryloxy, heteroarylthio, heteroarylamino or heteroaryl-N-(alkyl)amino orA and B, together with the C atom whose substituents they are, are an isocyclic or heterocyclic ring which can also be quinonoid,and fungicides containing these compounds.
    Type: Grant
    Filed: June 3, 1994
    Date of Patent: August 6, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhard Doetzer, Hubert Sauter, Herbert Bayer, Franz Roehl, Gisela Lorenz, Eberhard Ammermann, Horst Wingert
  • Patent number: 5527964
    Abstract: Azines of formula (I): ##STR1## in which R and R' either are identical and represent an alkyl radical containing 1 to 4 carbon atoms or an alkenyl radical containing 3 to 5 carbon atoms, or together form a radical of formula (II):--CHR.sub.1 --(CR.sub.2 R.sub.3).sub.n --CHR.sub.4 -- (II)in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4, identical or different, represent a hydrogen atom or an alkyl radical containing 1 to 4 carbon atoms and n represents 0 or 1, in their different stereoisomer forms, their preparation process and their use.
    Type: Grant
    Filed: April 28, 1995
    Date of Patent: June 18, 1996
    Assignee: Societe Francaise Hoechst
    Inventors: Alain Schouteeten, Yani Christidis
  • Patent number: 5288727
    Abstract: The present invention relates to a hydrazone compound of the formula (I) or its salt, a process for its preparation, an intermediate of the formula (II-5), a pesticidal composition containing said hydrazone compound or its salt as the active ingredient, and a pesticidal method of applying an effective amount thereof: ##STR1##
    Type: Grant
    Filed: February 13, 1992
    Date of Patent: February 22, 1994
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Tadaaki Toki, Toru Koyanagi, Kiyomitsu Yoshida, Hiroshi Sasaki, Masayuki Morita, Tetsuo Yoneda
  • Patent number: 5252309
    Abstract: Azines, well suited for hydrolysis into hydrazine, are prepared in high yields by reacting ammonia, aqueous hydrogen peroxide and a carbonyl compound reactant in the presence of a catalytically effective amount of a catalyst medium therefor, i.e., an aqueous solution of ammonium acetate and acetamide or of acetamide and acetic acid, but in the absence of CO.sub.2.
    Type: Grant
    Filed: June 12, 1992
    Date of Patent: October 12, 1993
    Assignee: Elf Atochem S.A.
    Inventors: Gerard Krempf, Bertrand Collier, Pierre Tellier, Jean-Pierre Schirmann
  • Patent number: 5239119
    Abstract: Azines are synthesized from aqueous hydrogen peroxide, ammonia and a carbonyl compound, e.g., acetone, methyl ethyl ketone or methyl isobutyl ketone, in the presence of a catalytically effective amount of immixture of an amide of a weak acid and an ammonium salt corresponding to such weak acid. A more general high output such process comprises (a) interreacting aqueous hydrogen peroxide, ammonia and a carbonyl compound in the presence of a catalytically effective amount of immixture comprising an amide of a weak acid, (b) separating the azine thus produced from the medium of reaction, (c) reconstituting the amount of the amide in the medium of reaction to the initial amount thereof present at the onset of step (a), and (d) recycling such reconstituted medium of reaction to step (a).
    Type: Grant
    Filed: November 25, 1991
    Date of Patent: August 24, 1993
    Assignee: Atochem
    Inventors: Jean-Pierre Schirmann, Pierre Tellier
  • Patent number: 4751326
    Abstract: An improved process for producing benzophenone-azine in which a catalyst can be removed, recovered and recycled is disclosed.
    Type: Grant
    Filed: December 20, 1984
    Date of Patent: June 14, 1988
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takanari Nawata, Shuzabu Sakaguchi, Toshiaki Kohzaki, Osamu Aoki, Norio Takeda, Masafumi Shimpo
  • Patent number: 4740619
    Abstract: A compound of the formula: ##STR1## wherein R is a hydrogen atom, a C.sub.1 -C.sub.4 alkoxy group, a C.sub.1 -C.sub.4 alkenyloxy group, a C.sub.3 -C.sub.4 alkynyloxy group, a C.sub.1 -C.sub.4 alkylthio group, a dichlorocyclopropylmethoxy group or a methyldichlorocyclopropylmethoxy group, X is a chlorine atom or a bromine atom and Y is a hydrogen atom, a fluorine atom or a chlorine atom, which is useful as a herbicide.
    Type: Grant
    Filed: February 3, 1987
    Date of Patent: April 26, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toru Haga, Eiki Nagano, Masayuki Takase, Ryo Sato
  • Patent number: 4727190
    Abstract: A process for continuously preparing benzophenone-azines comprising oxidizing benzophenone-imines with molecular oxygen or a molecular oxygen-containing gas in the presence of a copper halide catalyst is disclosed. The oxidation reaction is carried out in a multistage system under an oxygen partial pressure gradually decreasing from the former stage to the latter stage and at a conversion gradually decreasing from the former stage to the latter stage, while controlling the conversion so that the molar ratio of the benzophenone-imines to the copper halide in the final stage be maintained at 1 or more. By the process, the continuous reaction can stably be performed at a high conversion of the benzophenone-imines without involving insolubilization and sedimentation of the catalyst.
    Type: Grant
    Filed: October 14, 1986
    Date of Patent: February 23, 1988
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takanari Nawata, Shuzabu Sakaguchi, Toshiaki Kohzaki, Osamu Aoki, Norio Takeda, Yoshiyuki Aoki, Masafumi Shimpo
  • Patent number: 4647697
    Abstract: In a process for producing an azine compound which comprises reacting ammonia with a hypochlorite in an aqueous medium in the presence of a carbonyl compound selected from the group consisting of acetone and methyl ethyl ketone at room temperature or a higher temperature and an atmospheric or higher pressure, the amounts of the carbonyl compound and ammonia being 2 to 5 moles and 5 to 35 moles, respectively, per mole of available chlorine of the hypochlorite; the improvement wherein(i) the reaction is carried out at a temperature of about 25.degree. C. to about 60.degree. C.,(ii) the reaction is carried out by using calcium hypochlorite as the hypochlorite and while feeding an aqueous solution of calcium hypochlorite having an available chlorine concentration of 5 to 20% by weight to the reaction system, and(iii) the reaction is carried out while controlling the rate of feeding the aqueous solution of calcium hypochlorite to the reaction system such that the amount of available chlorine is 0.001 to 0.
    Type: Grant
    Filed: December 28, 1983
    Date of Patent: March 3, 1987
    Assignee: Nippon Carbide Kogyo Kabushiki Kaisha
    Inventors: Minekazu Koshi, Osamu Fukao, Taisuke Saito, Tatsuo Sakan, Seiichi Nakahara
  • Patent number: 4473708
    Abstract: A process for preparing a ketazine useful as an intermediate for the synthesis of hydrazine is disclosed. The process comprises reacting an aliphatic or aromatic ketone with ammonia and hydrogen peroxide in the presence of a catalyst of an arsenic compound to produce a corresponding ketazine.
    Type: Grant
    Filed: July 9, 1982
    Date of Patent: September 25, 1984
    Assignee: Mitsubishi Gas Chemical Company Inc.
    Inventors: Yasuhisa Kuriyama, Minoru Kakuda, Shoichi Nitoh
  • Patent number: 4446068
    Abstract: N-substituted fluoroaziridines useful as chemical intermediates and process or making by reaction of fluoroazines with fluorocarbenes.
    Type: Grant
    Filed: April 4, 1967
    Date of Patent: May 1, 1984
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: Ronald A. Mitsch
  • Patent number: 4423130
    Abstract: In an electrophotographic light-sensitive material having on a conductive support a light-sensitive layer composed of a charge generating material and a charge transporting material. A hydrazone compound is used as the charge transporting material for providing the light sensitive layer having high sensitivity and less residual surface potential. The light-sensitive layer is stable to oxidation by ozone generated by corona discharging as well as to heat and light, results in less dark decay of the surface potential. Furthermore, the layer shows less deviation in residual potential and sensitivity due to repeated use.
    Type: Grant
    Filed: March 11, 1982
    Date of Patent: December 27, 1983
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Seiji Horie, Junji Nakano, Hideo Sato
  • Patent number: 4420548
    Abstract: An electrophotographic photosensitive member is characterized by having a layer containing at least one of hydrazone group compounds represented by the following formula (1) or of ketazine group compounds represented by the following formula (2): ##STR1## In the formula, R.sub.11 and R.sub.12 independently of one another represent hydrogen, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic radical; R.sub.13 and R.sub.14 independently of one another represent subsituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic radical; and R.sub.15 represents a divalent organic residue. ##STR2## In the formula, R.sub.21, R.sub.22, R.sub.23, and R.sub.24 independently one another represent substituted or unsubstituted alkyl, substituted or substituted aralkyl, or substituted or unsubstituted aryl, or R.sub.21 and R.sub.
    Type: Grant
    Filed: November 16, 1981
    Date of Patent: December 13, 1983
    Assignee: Canon Kabushiki Kaisha
    Inventors: Kiyoshi Sakai, Minoru Mabuchi, Toshiko Suzuki, Yuji Egarashi, Shozo Ishikawa
  • Patent number: 4366165
    Abstract: This invention relates to 1 and 4-arylcyanoalkyl-1,2,4-triazoles, their enantiomorphs, and acid addition salts and metal salt complexes. This invention also relates to the method of preparation and use of these compounds. These compounds enantiomorphs, salts and complexes are highly active broad-spectrum systemic fungicides effective in controlling phytopathogenic fungi such as barley net blotch (Helminthosporium teres), grey mold (Botrytis cinerea), bean powdery mildew (Erysiphe polygoni), grape downy mildew (Plasmopora viticola), rice blast (Piricularia oryzae), tomato late blight (Phytophthora infestans) and wheat stem rust (Puccinia graminis f. sp. tritici race 15B-2).
    Type: Grant
    Filed: February 11, 1981
    Date of Patent: December 28, 1982
    Assignee: Rohm and Haas Company
    Inventors: George A. Miller, Hak-Foon Chan
  • Patent number: 4347383
    Abstract: A process for producing a benzophenone-azine which comprises reacting the corresponding benzophenone-imine with molecular oxygen or benzophenone with ammonia and molecular oxygen in the presence of a catalyst selected from the group consisting of metals, metal oxides and alloys of two or more metals, particularly copper or copper alloy-containing catalyst, is disclosed.
    Type: Grant
    Filed: May 6, 1980
    Date of Patent: August 31, 1982
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tomiya Isshiki, Tetsuo Tomita, Shuzabu Sakaguchi, Toshiaki Kohzaki, Osamu Aoki, Norio Takeda, Yoshiyuki Aoki
  • Patent number: 4317929
    Abstract: Isoindolinone pigments of the formula ##STR1## wherein X.sub.1, X.sub.2, X.sub.3 and X.sub.4 represent hydrogen or halogen atoms, or one or two of X.sub.1 -X.sub.4 represents alkoxy groups of 1 to 4 carbon atoms of phenoxy groups and the others represent hydrogen or halogen atoms, R and R" represent hydrogen or halogen atoms or methyl or methoxy groups, R.sub.1, R.sub.2, R.sub.4 and R.sub.5 represent hydrogen, chlorine or bromine atoms or alkyl groups of 1 to 2 carbon atoms, R.sub.3 and R.sub.6 represent hydrogen or halogen atoms, alkyl or alkoxy groups of 1 to 2 carbon atoms or radicals of the formula ##STR2## Q represents a direct bond or a p-phenylene group, n is 1 or 2 and X represents a group of the formula ##STR3## wherein R.sub.7 and R.sub.8 represent hydrogen or chlorine atoms or methyl groups.
    Type: Grant
    Filed: May 27, 1980
    Date of Patent: March 2, 1982
    Assignee: Ciba-Geigy Corporation
    Inventor: Ernst Model
  • Patent number: 4293714
    Abstract: This invention relates to copolymerizable ultraviolet light absorber compounds having the formula: ##STR1## where: R is alkylene oxyalkylene, alkyleneoxyalkylene or phenylene, which R groups are of up to 10 carbon atoms and are unsubstituted or substituted with hydroxy;R' and R" are independently hydrogen or alkyl; C.sub.1 -C.sub.6 ; andR'" is alkyl C.sub.1 -C.sub.6, substituted alkyl C.sub.1 -C.sub.6, or alkoxy C.sub.1 -C.sub.6.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: October 6, 1981
    Assignee: GAF Corporation
    Inventors: Bruce A. Gruber, Donald H. Lorenz
  • Patent number: 4265784
    Abstract: A light-control device includes a liquid crystal material sandwiched between a pair of planar, light-transmitting members. The liquid crystal material particularly includes an asymmetrical azine compound having the general formula: ##STR1## wherein R.sub.1 and R.sub.2 are different para-substituents selected from the group comprising cyano, halogen, alkyl, and substituted alkyl radicals in which the alkyl radical has from one to nine carbon atoms, and wherein X and Y are selected from the group comprising hydrogen and methyl radicals.
    Type: Grant
    Filed: July 27, 1979
    Date of Patent: May 5, 1981
    Assignee: General Electric Company
    Inventors: Hugh Mailer, Stanley Laskos, Jr.
  • Patent number: 4233242
    Abstract: Ketazines having the general formula (I) ##STR1## wherein R.sub.1 represents alkyl group having 1 to 4 carbon atoms and R.sub.2 represents (i) an alkyl group having 1 to 4 carbon atoms or (ii) a phenyl group optionally substituted with an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or a halogen group, and R.sub.1 and R.sub.2 together with the carbon atom to which they are both bonded may form a ring, are advantageously manufactured by reacting an aliphatic or aromatic ketone having the formula (II) ##STR2## wherein R.sub.1 and R.sub.2 are as defined above, with ammonia and a peroxide compound or compounds in the presence of amorphous silica or palladium compounds, as a catalyst, at a temperature of from 0.degree. to 120.degree. C., in a liquid phase.
    Type: Grant
    Filed: April 6, 1979
    Date of Patent: November 11, 1980
    Assignee: Showa Denko Kabushiki Kaisha
    Inventors: Nobuyuki Nagato, Yuichi Sugiyama
  • Patent number: 4231931
    Abstract: Isoindolinone pigments of the formula ##STR1## wherein X.sub.1, X.sub.2, X.sub.3 and X.sub.4 represent hydrogen or halogen atoms, or one or two of X.sub.1 -X.sub.4 represent alkoxy groups of 1 to 4 carbon atoms or phenoxy groups and the others represent hydrogen or halogen atoms, R and R" represent hydrogen or halogen atoms or methyl or methoxy groups, R.sub.1, R.sub.2, R.sub.4 and R.sub.5 represent hydrogen, chlorine or bromine atoms or alkyl groups of 1 to 2 carbon atoms, R.sub.3 and R.sub.6 represent hydrogen or halogen atoms, alkyl or alkoxy groups of 1 to 2 carbon atoms or radicals of the formula ##STR2## Q represents a direct bond or a p-phenylene group, n is 1 or 2 and X represents a group of the formula ##STR3## wherein R.sub.7 and R.sub.8 represent hydrogen or chlorine atoms or methyl groups.
    Type: Grant
    Filed: January 30, 1979
    Date of Patent: November 4, 1980
    Assignee: Ciba-Geigy Corporation
    Inventor: Ernst Model