Azines (i.e., Hch=n-n=hch, Wherein Substitution May Be Made For Hydrogen) Patents (Class 564/249)
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Patent number: 8871977Abstract: 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: GrantFiled: June 17, 2009Date of Patent: October 28, 2014Assignee: Zeon CorporationInventors: Kei Sakamoto, Yasushi Nakano
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Patent number: 8362273Abstract: Process for preparing aminale and their use for preparing 1,3-disubstituted pyrazole compounds.Type: GrantFiled: October 28, 2010Date of Patent: January 29, 2013Assignee: BASF SEInventors: Maximilian Dochnahl, Michael Keil, Roland Goetz
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Publication number: 20120215009Abstract: Process for preparing aminale and their use for preparing 1,3-disubstituted pyrazole compounds.Type: ApplicationFiled: October 28, 2010Publication date: August 23, 2012Applicant: BASF SEInventors: Maximilian Dochnahl, Michael Keil, Roland Goetz
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Patent number: 8158021Abstract: 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: GrantFiled: April 24, 2008Date of Patent: April 17, 2012Assignee: Zeon CorporationInventors: Kei Sakamoto, Naoto Kogoshi, Yoshihide Yachi
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Publication number: 20110144379Abstract: 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: ApplicationFiled: June 17, 2009Publication date: June 16, 2011Applicant: ZEON CORPORATIONInventors: Kei Sakamoto, Yasushi Nakano
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Patent number: 7932422Abstract: 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: GrantFiled: October 3, 2007Date of Patent: April 26, 2011Inventors: Anne Bertolotti, Marc Blondel
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Patent number: 7812113Abstract: 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: GrantFiled: July 4, 2006Date of Patent: October 12, 2010Assignee: Agfa Graphics NVInventors: Geert Deroover, Wojciech Jaunky, Lambertus Groenendaal, Johan Loccufier
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Publication number: 20100105950Abstract: 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: ApplicationFiled: February 14, 2008Publication date: April 29, 2010Inventors: Masatoshi Taniguchi, Koji Mori
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Patent number: 7501216Abstract: 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: GrantFiled: March 19, 2004Date of Patent: March 10, 2009Assignee: Samsung Electronics Co., Ltd.Inventors: Nusrallah Jubran, Zbigniew Tokarski, Kam W. Law
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Patent number: 7488353Abstract: Cationic heteroarylazine dyes of general formulas (I) and (II) and colorants for keratin fibers containing these compounds.Type: GrantFiled: December 2, 2004Date of Patent: February 10, 2009Assignee: Wella AGInventors: Markus Speckbacher, Hans-Juergen Braun
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Patent number: 7439396Abstract: 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: GrantFiled: April 14, 2006Date of Patent: October 21, 2008Assignee: Galderma Research & DevelopmentInventors: Thibaud Biadatti, Anne-Pascale Luzy
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Patent number: 7316877Abstract: 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: GrantFiled: October 29, 2004Date of Patent: January 8, 2008Assignee: Samsung Electronics Co., Ltd.Inventors: Nusrallah Jubran, Patrick Knoll
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Patent number: 7300732Abstract: 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: GrantFiled: February 10, 2004Date of Patent: November 27, 2007Assignee: Samsung Electronics Co., Ltd.Inventors: Nusrallah Jubran, Zbigniew Tokarski, Kam W. Law
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Patent number: 7261988Abstract: 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: GrantFiled: April 27, 2004Date of Patent: August 28, 2007Assignee: Samsung Electronics Co. LtdInventors: Zbigniew Tokarski, Nusrallah Jubran, Vytautas Getautis, Maryte Daskeviciene, Ingrida Paulauskaite, Robertas Maldzius, Jonas Sidaravicius
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Patent number: 7115347Abstract: 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: GrantFiled: January 16, 2004Date of Patent: October 3, 2006Assignee: Samsung Electronics Co., LTDInventors: Zbigniew Tokarski, Nusrallah Jubran, Vytautas Getautis, Valentas Gaidelis, Maryte Daskeviciene, Edmundas Montrimas, Ingrida Paulauskaite, Jonas Sidaravicius
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Patent number: 7034184Abstract: 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: GrantFiled: March 6, 2003Date of Patent: April 25, 2006Assignee: Daicel Chemical Industries, Ltd.Inventors: Yasutaka Ishii, Tatsuya Nakano
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Patent number: 6818794Abstract: 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: GrantFiled: November 27, 2002Date of Patent: November 16, 2004Assignee: Bayer AktiengesellschaftInventors: Ottfried Schlak, Hans-Georg Adams, Johannes Kaulen
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Publication number: 20040147746Abstract: 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: ApplicationFiled: December 4, 2003Publication date: July 29, 2004Applicant: Millennium Pharmaceuticals, Inc.Inventors: Tricia J. Vos, Michael Patane, Michael E. Solomon, Christopher Blackburn, Mihaela D. Danca
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Patent number: 6605265Abstract: 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: GrantFiled: March 25, 1994Date of Patent: August 12, 2003Assignee: AtochemInventors: Jean-Pierre Schirmann, Jean-Pierre Pleuvry, Pierre Tellier
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Patent number: 6562311Abstract: 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: GrantFiled: January 25, 2001Date of Patent: May 13, 2003Assignee: AtofinaInventors: Jean-Pierre Schirmann, Paul Bourdauducq
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Patent number: 6551568Abstract: 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: GrantFiled: April 5, 2001Date of Patent: April 22, 2003Assignee: AtofinaInventors: Georges Brenguer, Rémi Jullin, Jean-Philippe Ricard
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Patent number: 6410600Abstract: The invention relates to novel azines, to a process for their preparation and to their use as fungicides.Type: GrantFiled: October 19, 2000Date of Patent: June 25, 2002Assignee: Bayer AktiengesellschaftInventors: Dirk Backhaus, Bernd-Wieland Krüger, Peter Gerdes, Herbert Gayer, Martin Vaupel, Klaus Stenzel
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Patent number: 6265613Abstract: 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: GrantFiled: February 24, 1998Date of Patent: July 24, 2001Assignee: BASF AktiengesellschaftInventors: 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
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Patent number: 6229047Abstract: 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: GrantFiled: December 4, 1995Date of Patent: May 8, 2001Assignee: The Curators of the University of MissouriInventors: Ranier E. Glaser, Grace S. Chen
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Patent number: 6010642Abstract: 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 forType: GrantFiled: August 21, 1997Date of Patent: January 4, 2000Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Haruyoshi Takatsu, Sadao Takehara, Kiyofumi Takeuchi, Makoto Negishi, Norie Osawa, Masashi Osawa, Shinji Ogawa, Hirokazu Yanagihara
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Patent number: 5986134Abstract: 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: GrantFiled: July 19, 1996Date of Patent: November 16, 1999Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Yasuhisa Kuriyama, Nobuhiro Nagata, Kiyoshi Yoshida
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Patent number: 5612479Abstract: 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: GrantFiled: August 17, 1994Date of Patent: March 18, 1997Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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Patent number: 5600001Abstract: 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: GrantFiled: February 22, 1996Date of Patent: February 4, 1997Assignee: Societe Francaise HoechstInventors: Alain Schouteeten, Yani Christidis
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Patent number: 5543433Abstract: 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: GrantFiled: June 3, 1994Date of Patent: August 6, 1996Assignee: BASF AktiengesellschaftInventors: Reinhard Doetzer, Hubert Sauter, Herbert Bayer, Franz Roehl, Gisela Lorenz, Eberhard Ammermann, Horst Wingert
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Patent number: 5527964Abstract: 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: GrantFiled: April 28, 1995Date of Patent: June 18, 1996Assignee: Societe Francaise HoechstInventors: Alain Schouteeten, Yani Christidis
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Patent number: 5288727Abstract: 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: GrantFiled: February 13, 1992Date of Patent: February 22, 1994Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Tadaaki Toki, Toru Koyanagi, Kiyomitsu Yoshida, Hiroshi Sasaki, Masayuki Morita, Tetsuo Yoneda
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Patent number: 5252309Abstract: 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: GrantFiled: June 12, 1992Date of Patent: October 12, 1993Assignee: Elf Atochem S.A.Inventors: Gerard Krempf, Bertrand Collier, Pierre Tellier, Jean-Pierre Schirmann
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Patent number: 5239119Abstract: 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: GrantFiled: November 25, 1991Date of Patent: August 24, 1993Assignee: AtochemInventors: Jean-Pierre Schirmann, Pierre Tellier
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Patent number: 4751326Abstract: An improved process for producing benzophenone-azine in which a catalyst can be removed, recovered and recycled is disclosed.Type: GrantFiled: December 20, 1984Date of Patent: June 14, 1988Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takanari Nawata, Shuzabu Sakaguchi, Toshiaki Kohzaki, Osamu Aoki, Norio Takeda, Masafumi Shimpo
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Patent number: 4740619Abstract: 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: GrantFiled: February 3, 1987Date of Patent: April 26, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Toru Haga, Eiki Nagano, Masayuki Takase, Ryo Sato
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Patent number: 4727190Abstract: 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: GrantFiled: October 14, 1986Date of Patent: February 23, 1988Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takanari Nawata, Shuzabu Sakaguchi, Toshiaki Kohzaki, Osamu Aoki, Norio Takeda, Yoshiyuki Aoki, Masafumi Shimpo
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Patent number: 4647697Abstract: 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: GrantFiled: December 28, 1983Date of Patent: March 3, 1987Assignee: Nippon Carbide Kogyo Kabushiki KaishaInventors: Minekazu Koshi, Osamu Fukao, Taisuke Saito, Tatsuo Sakan, Seiichi Nakahara
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Patent number: 4473708Abstract: 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: GrantFiled: July 9, 1982Date of Patent: September 25, 1984Assignee: Mitsubishi Gas Chemical Company Inc.Inventors: Yasuhisa Kuriyama, Minoru Kakuda, Shoichi Nitoh
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Patent number: 4446068Abstract: N-substituted fluoroaziridines useful as chemical intermediates and process or making by reaction of fluoroazines with fluorocarbenes.Type: GrantFiled: April 4, 1967Date of Patent: May 1, 1984Assignee: The United States of America as represented by the Secretary of the NavyInventor: Ronald A. Mitsch
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Patent number: 4423130Abstract: 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: GrantFiled: March 11, 1982Date of Patent: December 27, 1983Assignee: Fuji Photo Film Co., Ltd.Inventors: Seiji Horie, Junji Nakano, Hideo Sato
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Patent number: 4420548Abstract: 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: GrantFiled: November 16, 1981Date of Patent: December 13, 1983Assignee: Canon Kabushiki KaishaInventors: Kiyoshi Sakai, Minoru Mabuchi, Toshiko Suzuki, Yuji Egarashi, Shozo Ishikawa
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Patent number: 4366165Abstract: 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: GrantFiled: February 11, 1981Date of Patent: December 28, 1982Assignee: Rohm and Haas CompanyInventors: George A. Miller, Hak-Foon Chan
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Patent number: 4347383Abstract: 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: GrantFiled: May 6, 1980Date of Patent: August 31, 1982Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tomiya Isshiki, Tetsuo Tomita, Shuzabu Sakaguchi, Toshiaki Kohzaki, Osamu Aoki, Norio Takeda, Yoshiyuki Aoki
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Patent number: 4317929Abstract: 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: GrantFiled: May 27, 1980Date of Patent: March 2, 1982Assignee: Ciba-Geigy CorporationInventor: Ernst Model
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Patent number: 4293714Abstract: 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: GrantFiled: March 20, 1980Date of Patent: October 6, 1981Assignee: GAF CorporationInventors: Bruce A. Gruber, Donald H. Lorenz
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Patent number: 4265784Abstract: 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: GrantFiled: July 27, 1979Date of Patent: May 5, 1981Assignee: General Electric CompanyInventors: Hugh Mailer, Stanley Laskos, Jr.
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Patent number: 4233242Abstract: 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: GrantFiled: April 6, 1979Date of Patent: November 11, 1980Assignee: Showa Denko Kabushiki KaishaInventors: Nobuyuki Nagato, Yuichi Sugiyama
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Patent number: 4231931Abstract: 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: GrantFiled: January 30, 1979Date of Patent: November 4, 1980Assignee: Ciba-Geigy CorporationInventor: Ernst Model