Formation Of Azo Group By Coupling Diazonium Compound With Coupling Component In Presence Of An Additional Organic Compound Patents (Class 534/581)
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Patent number: 10782625Abstract: The invention relates to the use of pigment mixtures which contain at least one pigment of formulas (la) and (lb), wherein variables X1, X2, X3, X4, Y1, Y2, Z1 and Z2 are as defined and wherein the pigment mixtures are useful as dyes in printing methods.Type: GrantFiled: May 31, 2016Date of Patent: September 22, 2020Assignee: Clariant Plastics & Coatings LtdInventors: Ulrike Rohr, Gemma Solduga Ramirez, Joachim Eichhorn
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Patent number: 9316936Abstract: The disclosure describes a pigment of certain surface area for use in toner.Type: GrantFiled: August 28, 2013Date of Patent: April 19, 2016Assignee: Xerox CorporationInventors: Kevin F Marcell, Maria M Barden, Kimberly Anne Stoll, Christopher M Wolfe, Brian J Andaya
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Publication number: 20140171628Abstract: A process for producing a charge control agent comprising an azo-based iron complex salt compound as an effective component, comprises: synthesizing a monoazo compound through diazotization coupling; and ironing the monoazo compound by using an ironizing agent such as ferric chloride to produce an azo-based iron complex salt compound represented by the following formula. The ironization reaction of the monoazo compound is carried out while pH is kept at 7.0 to 8.0. Since the above azo-based iron complex salt compound having high purity can be obtained at a high yield, it can be used as a charge control agent directly and a special purification step can be eliminated, thereby making it possible to greatly cut the production cost.Type: ApplicationFiled: March 5, 2013Publication date: June 19, 2014Applicant: HODOGAYA CHEMICAL CO., LTD.Inventors: Atsushi TAKESUE, Yoshihiko ABE, Hideyuki OTSUKA, Jun WATANABE, Shunsuke SAITOH, Kanae HIRAISHI
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Publication number: 20140085771Abstract: An organic compound has the following chemical structure: wherein R is different from R*; R and R* are independently hydrogen, halogen, nitro or methoxyl; and R1 is a C1-C6 alkyl or a phenyl group. A quaternary data storage device includes a bottom electrode, a top electrode, and the organic film layer sandwiched between the bottom electrode and the top electrode.Type: ApplicationFiled: December 12, 2012Publication date: March 27, 2014Applicant: Soochow UniversityInventors: Jian-Mei LU, Hua LI
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Publication number: 20120328984Abstract: To provide a process for producing an azo pigment showing excellent coloring characteristics such as tinctorial strength and hue and showing excellent fastness such as light fastness and ozone fastness, an azo pigment dispersion, a coloring composition, and an ink for inkjet recording. A process for producing, for example, an azo pigment represented by the general formula (9), which includes a step of preparing a solution containing a compound represented by the following general formula (7) and an acid, and a step of bringing the solution incontact with a diazonium salt (8) derived from a heterocyclic amine.Type: ApplicationFiled: January 14, 2011Publication date: December 27, 2012Applicant: FUJIFILM CORPORATIONInventors: Masahiro Higashi, Nobuo Seto, Yoshihiro Jimbo, Keiichi Tateishi
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Patent number: 8273877Abstract: Substituted tetraazapentalenes have two benzenoid rings and eight substitutable positions. Substitutions are made of hydrogen or C—H groups in favor of amino groups, nitro groups or nitrogen atoms. The tetraazapentalenes are synthesized through an intermediate azo, which is made from a 1:1:1 molar ratio of a nitroaniline, sodium nitrite and an amine.Type: GrantFiled: November 18, 2011Date of Patent: September 25, 2012Assignee: The United States of America as Represented by the Secretary of the NavyInventors: Alfred G. Stern, Patrick A. Caruana
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Publication number: 20120101264Abstract: Rinsable dyes with improved fugitivity are formulated by attaching dyestuff compounds with amine-capped sulfonic solubilizing groups to commercially available ethoxylated aniline, so that the surfactant effect of the ethoxylated aniline counteracts the substantivity of the dyestuff compound, while the neutralization of the sulfonic solubilizing groups reduces substantivity.Type: ApplicationFiled: December 2, 2011Publication date: April 26, 2012Inventors: Mark Berenfeld, Sal Harfouch, Peter Caputo
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Patent number: 7927384Abstract: Compounds of the general formula (I) a process for their preparation and their use for dyeing and/or printing organic substrates are described.Type: GrantFiled: June 21, 2007Date of Patent: April 19, 2011Assignee: Clariant Finance (BVI) LimitedInventor: Rainer Nusser
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Patent number: 7772376Abstract: A process for the preparation of a desired chemical compound in a continuous reactor in which a part of the product stream exits the reactor and part of the product stream is recycled around the reactor in order to reduce the amount of buffer that would otherwise be required.Type: GrantFiled: July 18, 2005Date of Patent: August 10, 2010Assignee: Fujifilm Imaging Colorants LimitedInventors: David Martin Payne, Douglas John Edwin Spencer, John Heathcote Atherton, Zachary Richard Meadows
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Patent number: 7754273Abstract: The present invention relates to a method of printing a substrate, comprising (a) printing onto the substrate at least one time temperature indicator with chromic properties based on an azo coupling reaction between a capped diazonium component and a coupling component.Type: GrantFiled: August 3, 2005Date of Patent: July 13, 2010Assignee: Ciba Specialty Chemicals Corp.Inventors: Hans Reichert, Bernhard Müller
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Publication number: 20100159210Abstract: The invention provides a compound of Formula (1): wherein: A and D each independently represent optionally substituted aryl or optionally substituted heteroaryl; E represents optionally substituted pyrazolyl; Z represents H, halogen, nitro, cyano, hydroxy, amino, carboxy, optionally substituted alkyl, optionally substituted alkoxy or optionally substituted aryloxy; and p is an integer from 0 to 5; provided that E has an optionally substituted carbonamide group of formula —CONR1R2 directly attached to it, wherein R1 and R2 each independently represent H, optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl. Also provided are ink compositions containing the compound and processes for printing an image using such compositions, preferably ink jet printing processes.Type: ApplicationFiled: July 31, 2006Publication date: June 24, 2010Inventors: Lilian Monahan, Philip John Double, Roy Bradbury, Lynn Patricia Bradbury
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Patent number: 7708824Abstract: In C. I. pigment red 57:1 of the present invention, the total content of 3-hydroxy-2-naphthoic acid and a metal salt thereof, which is measured by quantitative analysis using liquid chromatography, is 2,500 ppm or less as converted into the 3-hydroxy-2-naphthoic acid.Type: GrantFiled: June 4, 2007Date of Patent: May 4, 2010Assignee: DIC CorporationInventors: Akihiro Ogata, Nagatoshi Kobayashi, Keiko Otsubo
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Publication number: 20090294762Abstract: Provided are an electron donor-azo-electron acceptor compound having a thiol-based anchoring group, a method of synthesizing the compound, and a molecular electronic device having a molecular active layer formed of the compound. The compound for forming a molecular electronic device includes an azo compound that has a dinitrothiophene group and an aminobenzene group having thiol derivatives. The compound forms a molecular active layer in the molecular electronic devices. The molecular active layer is self-assembled on an electrode using the thiol derivative in the azo compound as an anchoring group. The molecular active layer in the molecular electronic device forms a switching device switching between an on-state and an off-state in response to a voltage applied to electrodes or a memory device storing a predetermined electric signal in response to a voltage applied to the electrodes.Type: ApplicationFiled: April 28, 2009Publication date: December 3, 2009Inventors: Hyoyoung Lee, Junghyun Lee, Heeyoel Baek, Gyeong Sook Bang, Jonghyurk Park, Nak-Jin Choi, Kun Jun, Seung Rim Shin
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Patent number: 7521545Abstract: A process for the production of an aromatic azo compound having a 2,3-dihydrobenzofuran ring bearing a diazo group at the 5-position of the ring by conducting the diazo coupling of a 2,3-dihydrobenzofuran derivative represented by the general formula (II): [wherein R1 and R2 are each independently C1-6 alkyl; R3 is optionally substituted aryl; and R4, R5 and R6 are each independently hydrogen, C1-6 alkyl, halogeno, C1-6 alkoxy, or C1-6 alkylthio] with a benzenediazonium salt having an electron-withdrawing group at the p- and/or o-position in a mixed solvent composed of water and a polar organic solvent.Type: GrantFiled: August 25, 2005Date of Patent: April 21, 2009Assignee: Takeda Pharmaceutical Company LimitedInventors: Tomomi Ikemoto, Takeshi Yamasaki
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Patent number: 7439339Abstract: A process for forming a diazo compound comprises reacting an organic compound bearing an acidic hydrogen with an aryl-diazonium salt in the presence of an inorganic base and a non-halogenated solvent. The process is simpler and more environmentally friendly than known processes.Type: GrantFiled: April 19, 2005Date of Patent: October 21, 2008Assignee: Eastman Kodak CompanyInventor: Catherine Mineur
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Patent number: 7402369Abstract: The present invention is to provide a charge controlling agent and negatively chargeable toner that do not contain any toxic metal, are essentially free from the risk of evoking ignition or explosion, and can exhibit a high charge amount and rapid initial increase in charging. The charge controlling agent is a mono azo iron complex compound represented by Formula (1): wherein J represents H, alkali metal, ammonium, or alkyl ammonium, or two or more of those elements in combination.Type: GrantFiled: September 29, 2006Date of Patent: July 22, 2008Assignee: Hodogaya Chemical Co., Ltd.Inventors: Masaki Okubo, Hideyuki Otsuka, Kazuo Nemoto, Masami Ito, Eisuke Yamada
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Publication number: 20080161545Abstract: The present invention relates to novel dyestuffs of formula (I) wherein the substituents have the meanings defined in the claims, the production of such dyestuffs, the use of these dyestuffs and material dyed or printed by such dyestuffs.Type: ApplicationFiled: December 12, 2005Publication date: July 3, 2008Inventors: Robert Egli, Thomas Grabenstein
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Patent number: 7074906Abstract: Provided is a novel one-pot, organic solvent-free process for the preparation of 2-(2-nitrophenylazo) substituted phenols. The 2-(2-nitrophenylazo) substituted phenols are precursors for hydroxyphenylbenzotriazole UV absorbers.Type: GrantFiled: November 26, 2002Date of Patent: July 11, 2006Assignee: Ciba Specialty Chemicals CorporationInventors: Stephen Daniel Pastor, Joseph Suhadolnik, Deborah Judd, Mervin Gale Wood
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Patent number: 6923856Abstract: A process for the preparation of organic pigments with enhanced fluorescence, which process comprises treating said pigments with a surfactant, and to the fluorescent organic pigments obtained by said process. The pigments according to the present invention can be used in marking applications, wherein durable fluorescence is required.Type: GrantFiled: November 8, 2001Date of Patent: August 2, 2005Assignee: Ciba Specialty Chemicals CorporationInventors: Iain Frank Fraser, Sharon Kathleen Wilson, Ian Alexander Macpherson
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Patent number: 6913640Abstract: Novel improved single-phase mixed crystals of monoazo dyes laked with alkaline earth metal cations and ammonium cations in a molar ratio of about 1:2 having a fine particle size and substantially better fastness properties than similar known products are excellently suitable as tinctorially strong pigments. Also claimed is a process for the preparation of a single-phase mixed crystal pigment of formula wherein E is Mg, Ca or Sr, by crystallisation from an inert hydrophilic liquid in the presence of solvated catiens E++, NR5R6R7R8+, x is a number from 0.33 to 0.62 and y is a number from 0.76 to 1.34, and the concentration of solvated catiens E++ at the beginning of the crystallisation is higher than the concentration of solvated cations NR5R8R7R8+.Type: GrantFiled: January 15, 2002Date of Patent: July 5, 2005Assignee: CIBA Specialty ChemicalsInventors: Philippe Bugnon, Carolin Sansonnens, Greig Chisholm
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Patent number: 6913641Abstract: The invention relates to novel monoazo compounds of formula (1), wherein R represents H or Cl, M2+ represents Ca2+ or SR2+ and Y1=H and Y2=SO3? or Y1=SO3? and Y2=H. The compounds of formula (1) are characterized by their high drying power and high light-fastness.Type: GrantFiled: April 27, 2002Date of Patent: July 5, 2005Assignee: Clariant GmbHInventors: Hans Joachim Metz, Uday T. Nabar, Frank Morgenroth, Chandrashekhar D. Patil, Sunil D. Deval
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Patent number: 6902612Abstract: Disclosed is a red pigment represented by Formula I: having a unique X-ray diffraction pattern. Also disclosed is a red pigment composition containing the pigment represented by Formula I and a surfactant. Also disclosed is a method of making a red pigment composition. Further disclosures relate to coating compositions, ink compositions, plastic compositions, electrostatic toner compositions, powder coating compositions, paint compositions, and paper compositions containing the red pigment represented by Formula I.Type: GrantFiled: September 8, 2003Date of Patent: June 7, 2005Assignee: Engelhard CorporationInventor: Amrit P. Bindra
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Patent number: 6756486Abstract: Disclosed are green shade yellow pigments represented by the Formula I: wherein R1 and R2 are independently selected from hydrogen, hydroxy, halogen, an alkyl group having 1 to about 4 carbon atoms, an alkoxy group having 1 to about 4 carbon atoms, a halo-alkyl group containing 1 to about 4 carbon atoms, an alkoxy carbonyl group having 1 to about 5 carbon atoms; R3 and R4 are independently selected from hydrogen, hydroxy, halogen, an alkyl group containing from 1 to about 4 carbon atoms, an alkoxy group containing from 1 to about 4 carbon atoms, and halo-alkyl groups containing from 1 to about 4 carbon atoms; and M is at least one divalent metal. Also disclosed are methods of making the green shade yellow pigments, methods of using the green shade yellow pigments, and coating compositions, ink compositions, electrostatic toner compositions, paint compositions, paper compositions, and plastic compositions containing the green shade yellow pigments.Type: GrantFiled: September 18, 2003Date of Patent: June 29, 2004Assignee: Engelhard CorporationInventors: Amrit P. Bindra, Steven A. Zamborsky
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Patent number: 6756485Abstract: Charge control agent comprising a metal complex salt compound of Formula (I) containing substantially no monoazo compound constituting the ligand thereof, toner containing the charge control agent, and process for manufacturing a metal complex salt compound of Formula (I), which comprises a metallizing reaction for metallizing a monoazo compound of Formula (II) with iron, nickel, aluminum, titanium or zirconium to produce a metal complex salt compound, in which metallizing reaction a monohydric or dihydric alcohol is used as a reaction-promoting solvent: R: alkyl (C4 to 12); Y: halogen or alkyl (C 1 to 5); p and q: number of monoazo compounds coordinated to the metal M; p: 1, 2, 3 or 4; q: 0, 1, 2 or 3; p+q: 1 to 6; L1 and L2 is —O—; one of L3 and L4 is —O—, while the other is an —OH group or an —O− ion; M is iron, nickel, aluminum, titanium or zirconium; (Mx+)m: m number of metals of atomic valence x; m: 1 to 4; x: 2 or more; Z−: theType: GrantFiled: February 11, 2003Date of Patent: June 29, 2004Assignee: Orient Chemical Industries, Ltd.Inventors: Masashi Yasumatsu, Akihiro Tada, Shun-ichiro Yamanaka
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Patent number: 6706863Abstract: The present invention provides Pigment Yellow 180 having an excellent transparency produced by using a fine slurry of 5-acetoacetylamino-benzimidazolone as a coupling component when Pigment Yellow 180 is produced by coupling reaction of 5-acetoacetylamino-benzimidazolone and diazo component obtained by diazotization of 1,2-bis(2-aminophenoxy)ethane.Type: GrantFiled: August 15, 2002Date of Patent: March 16, 2004Assignee: Clariant Finance (BVI) LimitedInventors: Isao Hashimoto, Noboru Tsuda, Hiroshi Ohsawa, Tomonori Okazaki, Manabu Shiga, Kohei Ohtsuki
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Patent number: 6576748Abstract: Disclosed is a process for preparing a diazopyridone compound either (A) of the formula or (B) of the formula which comprises diazotizing a dianiline and coupling it with a pyridone or diazotizing an aniline and coupling it with a dipyridone.Type: GrantFiled: June 27, 2002Date of Patent: June 10, 2003Assignee: Xerox CorporationInventors: Rina Carlini, James D. Mayo, James M. Duff, Jeffrey H. Banning, Paul F. Smith, George Liebermann, Roger E. Gaynor
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Patent number: 6566507Abstract: Provided is a process for preparing 2H-benzotriazole UV absorbers containing a perfluoroalkyl moiety at the 5-position of the benzo ring, for example a trifluoromethyl group, which involves diazotizing the perfluoroalkyl substituted o-nitroaniline using concentrated sulfuric acid plus sodium nitrite or nitrosylsulfuric acid to form the corresponding monoazobenzene intermediate via the diazonium salt intermediate which is reduced to the corresponding 5-perfluoroalkyl substituted 2H-benzotriazole UV absorber compound by conventional reduction means. Also provided is a novel one-pot, multiphase reaction for the preparation of 2(2-nitrophenylazo) substituted phenols, which are precursors for 2H-benzotriazole UV absorbers.Type: GrantFiled: May 31, 2001Date of Patent: May 20, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: Mervin G. Wood, Deborah DeHessa, Joseph Suhadolnik, Andrew B. Naughton, Jerome Sanders, Jacqueline Lau, Rong Xiong, Joseph Babiarz
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Publication number: 20030054281Abstract: A dye-forming method comprising: reacting a dye-forming coupler and a color developing agent precursor represented by the following general formula (I): 1Type: ApplicationFiled: November 14, 2001Publication date: March 20, 2003Inventors: Kensuke Morita, Shun-ichi Ishikawa, Hideaki Naruse, Koki Nakamura, Toshio Kawagishi, Tadashi Ohmatsu, Kozo Aoki
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Patent number: 6375733Abstract: Disclosed are blue shade red to magenta monoazo pigments which are obtained by diazotization of 5-alkoxy-2-aminobenzenesulfonic acids, coupling of the diazonium compound with a hydoxynaphthalenesulfonic acid and subsequent laking of the coupling product with a divalent metal salt. The pigments are characterized by the formula: wherein R is a lower alkyl, e.g. a methyl or ethyl group, or a hydroxycarbyl group, R1 is hydrogen, chloro, a lower alkyl group such as methyl or ethyl, or a lower alkoxy group such as a methoxy or an ethoxy group, and M is Ca, Sr, Ba, Mn, Mg or Zn. The new pigments have a magenta color, excellent heat stability, bleed fastness and very high color strength. These pigments are suitable for the pigmenting of plastics, inks and coatings, among other materials.Type: GrantFiled: August 28, 2000Date of Patent: April 23, 2002Assignee: Engelhard CorporationInventor: Amrit P. Bindra
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Patent number: 6281338Abstract: Mono- or dipotassium salts of azo compounds conforming to the formula (I) or one of its tautomeric structures where R and R′ are independently OH, NH2, NH—CN, acylamino or arylamino and R1 and R1′are independently —OH or —NH2, and also their hydrates.Type: GrantFiled: September 19, 2000Date of Patent: August 28, 2001Assignee: Bayer AktiengesellschaftInventors: Richard Sommer, Frank Linke, Udo Herrmann
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Patent number: 6254671Abstract: In one embodiment, the present invention relates to a green shade yellow pigment composition comprising a compound having the formula: wherein R1 and R2 are independently hydrogen, halogen, an alkyl group having 1 to about 4 carbon atoms, an alkoxy group having 1 to about 4 carbon atoms, an alkoxycarbonyl group having 1 to about 6 carbon atoms, nitro, cyano, phenoxy or trifluoromethyl; and M2+ is a divalent metal. The green shade yellow pigment composition is suitable for use in plastics, paints, inks, electrostatic toners, powder coatings, and paper.Type: GrantFiled: November 15, 1999Date of Patent: July 3, 2001Assignee: Engelhard CorporationInventor: Byron G. Hays
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Patent number: 6235100Abstract: In one embodiment, the present invention relates to a method of preparing a medium shade yellow pigment composition comprising making an azo pigment by coupling (i) two or more diazonium components made from two or more aromatic amines including 2-amino-5-chloro-4-ethylbenzene-1-sulfonic acid and 2-amino-4-chloro-5-methylbenzene-1-sulfonic acid with (ii) at least 1-(3′-sulfophenyl)-3-methyl-5-pyrazolone, and metallizing the azo pigment with a divalent metal to provide the medium shade yellow pigment composition. The medium shade yellow pigment composition is suitable for use in plastics, paints and inks.Type: GrantFiled: June 24, 1999Date of Patent: May 22, 2001Assignee: Engelhard CorporationInventor: Byron G. Hays
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Patent number: 6150509Abstract: A water-insoluble yellow monoazo pigment has the following formula (I): ##STR1##Type: GrantFiled: November 12, 1999Date of Patent: November 21, 2000Assignee: Dominion Colour CorporationInventors: Alan Gray, Henry Lui, Dorothy-Grace Manarang
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Patent number: 6133432Abstract: A process for preparing a compound of the formula ##STR1## wherein R is C.sub.1 -C.sub.18 alkyl by reacting a compound of the formulaRO.sub.2 C--CH.sub.2 CN (II)with a cyanide salt and formaldehyde or source thereof. Compounds of formula (I) are useful intermediates to pesticidally active compounds.Type: GrantFiled: December 1, 1998Date of Patent: October 17, 2000Assignee: Rhone-Poulenc AgroInventors: David William Hawkins, David Alan Roberts, John Harry Wilkinson, Jean-Louis Clavel
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Patent number: 6111083Abstract: Disperse dyes of formula ##STR1## wherein R.sub.1 is nitro or cyano, R.sub.2 is halogen, R.sub.3 is C.sub.1 -C.sub.4 alkyl, R.sub.4 and R.sub.5 are each independently of the other methyl or ethyl and R.sub.6 is hydrogen, methyl or ethyl, with the proviso that R.sub.6 is not hydrogen if R.sub.1 is cyano, R.sub.2 is halogen and R.sub.3 is methyl or isopropyl or if R.sub.1 is nitro, R.sub.2 is halogen and R.sub.3 is methyl.These dyes are suitable in particular for dyeing and printing polyester textile materials.Type: GrantFiled: April 20, 1999Date of Patent: August 29, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Antoine Clement, Alfons Arquint, Urs Lauk
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Patent number: 6090927Abstract: The invention relates to novel intermediates in a process for preparing compounds having the formula: ##STR1## wherein R.sub.3, R.sub.4, R.sub.6 and Ar are as defined in the description, by reaction of a compound of formula (I) with a compound of formula (II) according to the following reaction scheme: ##STR2## The compounds of formula (IV) are useful as pesticides.Type: GrantFiled: February 16, 1999Date of Patent: July 18, 2000Assignee: Rhone-Poulenc Inc.Inventor: Peter Wyatt Newsome
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Patent number: 6028178Abstract: Azo pigment of the formula (1) ##STR1## which has a specific surface area of the pigment powder of more than 45 m.sup.2 /g.The azo pigment is particularly suitable as colorant in electrophotographic toners and developers, and in powder coatings and electret materials.Type: GrantFiled: July 26, 1999Date of Patent: February 22, 2000Assignee: Clariant GmbHInventors: Hans Joachim Metz, Rudiger Baur, Hans-Tobias Macholdt
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Patent number: 5998592Abstract: A monoazo dye of the formula: ##STR1## wherein: R.sup.1 represents --C.sub.3 H.sub.6 CN, --C.sub.2 H.sub.4 Cl, --C.sub.3 H.sub.6 Cl, --C.sub.2 H.sub.4 OCOCH.sub.3 or --C.sub.2 H.sub.4 OCOCH.sub.2 Cl;R.sup.2 and R.sup.3 each independently represent a C.sub.1-4 -alkyl group; andR.sup.4, R.sup.5 and R.sup.6 each independently represent H, F, Cl, Br, I, --SO.sub.2 F, or an organic moiety selected from the group consisting of C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-4 alkanoylamino, --NHSO.sub.2 alkyl, --NHCOC.sub.1-4 alkyl and -Ophenyl moieties, each organic moiety being unsubstituted or substituted by at least one nonionic substituent.Type: GrantFiled: August 17, 1998Date of Patent: December 7, 1999Assignee: BASF AktiengesellschaftInventor: Nigel Hall
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Patent number: 5973126Abstract: A monoazo compound synthesized using 2-hydroxynaphthalene-3,6-dicarboxylic acid (or salt thereof), an amide, an ureide or an ester thereof as a coupler is novel, and is superior in water resistance, chemical resistance and solvent resistance. The present invention provides such a novel azo compound and a process for producing the same.Type: GrantFiled: May 20, 1998Date of Patent: October 26, 1999Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Masaya Kitayama, Kenji Minami, Hiroyuki Wakamori
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Patent number: 5964899Abstract: Azo dyes containing sulphur dye entities as a constitutional component are dyes of valuable properties, in particular for the dyeing of leather.Type: GrantFiled: October 8, 1997Date of Patent: October 12, 1999Assignee: Clariant Finance (BVI) LimitedInventors: Jordi Berenguer, Manuel Jose Domingo, Jose Rocas
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Patent number: 5942604Abstract: A dye mixture, which comprises as component (A) a dye of formula as component (B) a dye of formula ##STR1## and/or as component (C) a dye of formula ##STR2## wherein D, X and Y are as defined in the specification. These dyes are particularly suitable for dyeing polyester fiber textile material.Type: GrantFiled: February 20, 1998Date of Patent: August 24, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Paul Herzig, Antoine Clement, Romeo Dreier, Alfons Arquint
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Patent number: 5889162Abstract: In one embodiment, the present invention relates to a green shade yellow pigment composition comprising a compound having the formula: ##STR1## wherein R.sub.1 and R.sub.2 are independently hydrogen, halogen, an alkyl group having 1 to about 4 carbon atoms, an alkoxy group having 1 to about 4 carbon atoms, an alkoxycarbonyl group having 1 to about 6 carbon atoms, nitro, cyano, phenoxy or trifluoromethyl. The green shade yellow pigment composition is suitable for use in plastics, paints and inks.Type: GrantFiled: August 10, 1998Date of Patent: March 30, 1999Assignee: Engelhard CorporationInventor: Byron G. Hays
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Patent number: 5869628Abstract: Disperse dyes of formula ##STR1## wherein R.sub.1 is chloro or bromo,R.sub.2 is methyl or ethyl, andR.sub.3 is methyl or ethyl.The dyes are particularly suitable for dyeing or printing polyester fiber textile material.Type: GrantFiled: August 26, 1997Date of Patent: February 9, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Paul Herzig, Antoine Clement
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Patent number: 5852179Abstract: The use of alkoxylated acetylenic diol surfactants in the aqueous synthesis of disperse azo dyes provides a simple process for improving filtration properties of dyestuff. The surfactants may be added prior to the coupling step of the synthesis or prior to heat treatment of the dye slurry. Advantages that are realized by incorporation of the surfactants into the synthesis include decreased filtration time, increased solid content in filter cake, improved washing properties of filter cake, and increased dye yield. In addition, for azo dyes that are synthesized as non-heat-stable crystal modifications, the presence of alkoxylated acetylenic diol surfactants in the dye slurry is effective in promoting the conversion of the dye to the desired thermally stable crystal modification.Type: GrantFiled: May 27, 1998Date of Patent: December 22, 1998Assignee: Air Products and Chemicals, Inc.Inventor: Gregory Paul Dado
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Patent number: 5824117Abstract: The present invention relates to the dyestuff of the formula I ##STR1## modifications of this dyestuff which are stable during dyeing, processes for the preparation thereof and their use for dyeing and printing synthetic fiber materials.Type: GrantFiled: June 28, 1996Date of Patent: October 20, 1998Assignee: Dystar Japan Ltd.Inventors: Ulrich Buhler, Jurgen Kuhlwein, Hubert Kruse
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Patent number: 5770708Abstract: A process for preparing aqueous preparations of azo dyes of the formula ##STR1## where R is hydrogen or C.sub.1 -C.sub.4 -alkyl andKat.sym. is the equivalent of a cation which derives from a tertiary amine of the ethanolamine or propanolamine series,by diazotization of an aniline of the formula ##STR2## with neopentylglycol dinitrite in an aqueous medium and coupling of the resulting reaction mixture with .beta.-naphthol in the presence of a water-miscible diluent and of an amine comprises using an amine comprising a tertiary amine of the ethanolamine or propanolamine series.Type: GrantFiled: May 27, 1997Date of Patent: June 23, 1998Assignee: BASF AktiengesellschaftInventor: Rudolf Bermes
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Patent number: 5747566Abstract: Compound of the general formula (I) ##STR1## in which X is an O or S atom or an imino group,Y is an O atom or an imino group,R.sub.1 and R.sub.2 are a hydrogen atom, C.sub.1 -C.sub.4 -alkyl, an unsubstituted phenyl group or a substituted phenyl group having 1 to 5 substituents from the group consisting of C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, nitro, cyano, hydroxyl, CF.sub.3, CONH.sub.2, CONH(C.sub.5 -C.sub.6 -cycloalkyl), CON(C.sub.1 -C.sub.4 -alkyl).sub.2, CONH(C.sub.1 -C.sub.4)-alkyl, COO(C.sub.1 -C.sub.4)-alkyl, COO(C.sub.5 -C.sub.6 -cycloalkyl) and CONH(phenyl), with the proviso that at least one of the radicals R.sub.1 or R.sub.2 has one of the meanings mentioned which differ from hydrogen,R.sub.3 is a hydrogen atom, a trifluoromethyl group, a halogen atom or a C.sub.1 -C.sub.4 -alkyl, a C.sub.1 -C.sub.4 -alkoxy, a nitro or a cyano group andR.sub.4 and R.sub.5 independently of one another are a hydrogen atom, C.sub.1 -C.sub.Type: GrantFiled: August 8, 1996Date of Patent: May 5, 1998Assignee: Hoechst AktiengesellschaftInventor: Joachim Weber
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Patent number: 5744588Abstract: A blue type disperse dye mixture comprising 1.0 part by weight of at least one dye of the formula (1), from 0 to 0.2 part by weight of at least one dye of the formula (2), from 0.05 to 1.0 part by weight of at least one dye of the formula (3) and from 0.05 to 1.0 part by weight of at least one dye of the formula (4): ##STR1## wherein X is a chlorine atom or a bromine atom, R.sup.1 is a C.sub.1-5 alkyl group, R.sup.2 is a C.sub.1-4 alkyl group, and R.sup.3 is a C.sub.1-5 alkyl group or an allyl group, provided that R.sup.1, R.sup.2 and R.sup.3 may, respectively, be the same or different among the formulae (1) to (4).Type: GrantFiled: October 9, 1996Date of Patent: April 28, 1998Assignee: DyStar Japan Ltd.Inventors: Kiyoshi Himeno, Toshio Hihara, Yousuke Takahashi
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Patent number: 5697985Abstract: This invention relates to a process for the preparation of storage-stable dye dispersions of alkali metal salts of anionic azo direct dyes by(a) preparing an aqueous slurry of an alkali metal salt of an azo direct dye, said salt having a solubility in water at 25.degree. C. of about 0.1 to about 15% by weight, by azo coupling one or more aromatic diazonium salts with one or more couplers while maintaining a pH of at least about 5 by adding a basic alkali metal compound in the absence of a nitrogen-containing base;(b) optionally, stirring the aqueous slurry at a temperature of about 5.degree. C. to about 100.degree. C. for up to about six hours;(c) optionally, adjusting the temperature of the aqueous slurry to about 5.degree. C. to about 40.degree. C.; and(d) adding to the aqueous slum/a viscosity enhancing agent in an amount sufficient to obtain a viscosity, determined at a temperature of about 20.degree. to about 25.degree. C.Type: GrantFiled: May 24, 1996Date of Patent: December 16, 1997Assignee: Bayer CorporationInventors: James J. Good, Tanya T. Harper, Samuel S. Murphree, John G. Skabardonis
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Patent number: 5677435Abstract: Disclosed are compositions comprising one or more compounds characterized by the formula: ##STR1## wherein R and R.sub.1 are independently hydrogen, chloro, methyl or ethyl groups.A process for preparing azo pigment compositions is also disclosed.Paint, ink and plastic compositions containing the foregoing pigments compositions are disclosed.Type: GrantFiled: September 24, 1996Date of Patent: October 14, 1997Assignee: Engelhard CorporationInventor: Amrit Bindra