Formation Of Azo Group By Coupling Diazonium Compound With Coupling Component In Presence Of An Additional Organic Compound Patents (Class 534/581)
  • Patent number: 10782625
    Abstract: 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: Grant
    Filed: May 31, 2016
    Date of Patent: September 22, 2020
    Assignee: Clariant Plastics & Coatings Ltd
    Inventors: Ulrike Rohr, Gemma Solduga Ramirez, Joachim Eichhorn
  • Patent number: 9316936
    Abstract: The disclosure describes a pigment of certain surface area for use in toner.
    Type: Grant
    Filed: August 28, 2013
    Date of Patent: April 19, 2016
    Assignee: Xerox Corporation
    Inventors: Kevin F Marcell, Maria M Barden, Kimberly Anne Stoll, Christopher M Wolfe, Brian J Andaya
  • Publication number: 20140171628
    Abstract: 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: Application
    Filed: March 5, 2013
    Publication date: June 19, 2014
    Applicant: HODOGAYA CHEMICAL CO., LTD.
    Inventors: Atsushi TAKESUE, Yoshihiko ABE, Hideyuki OTSUKA, Jun WATANABE, Shunsuke SAITOH, Kanae HIRAISHI
  • Publication number: 20140085771
    Abstract: 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: Application
    Filed: December 12, 2012
    Publication date: March 27, 2014
    Applicant: Soochow University
    Inventors: Jian-Mei LU, Hua LI
  • Publication number: 20120328984
    Abstract: 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: Application
    Filed: January 14, 2011
    Publication date: December 27, 2012
    Applicant: FUJIFILM CORPORATION
    Inventors: Masahiro Higashi, Nobuo Seto, Yoshihiro Jimbo, Keiichi Tateishi
  • Patent number: 8273877
    Abstract: 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: Grant
    Filed: November 18, 2011
    Date of Patent: September 25, 2012
    Assignee: The United States of America as Represented by the Secretary of the Navy
    Inventors: Alfred G. Stern, Patrick A. Caruana
  • Publication number: 20120101264
    Abstract: 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: Application
    Filed: December 2, 2011
    Publication date: April 26, 2012
    Inventors: Mark Berenfeld, Sal Harfouch, Peter Caputo
  • Patent number: 7927384
    Abstract: Compounds of the general formula (I) a process for their preparation and their use for dyeing and/or printing organic substrates are described.
    Type: Grant
    Filed: June 21, 2007
    Date of Patent: April 19, 2011
    Assignee: Clariant Finance (BVI) Limited
    Inventor: Rainer Nusser
  • Patent number: 7772376
    Abstract: 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: Grant
    Filed: July 18, 2005
    Date of Patent: August 10, 2010
    Assignee: Fujifilm Imaging Colorants Limited
    Inventors: David Martin Payne, Douglas John Edwin Spencer, John Heathcote Atherton, Zachary Richard Meadows
  • Patent number: 7754273
    Abstract: 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: Grant
    Filed: August 3, 2005
    Date of Patent: July 13, 2010
    Assignee: Ciba Specialty Chemicals Corp.
    Inventors: Hans Reichert, Bernhard Müller
  • Publication number: 20100159210
    Abstract: 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: Application
    Filed: July 31, 2006
    Publication date: June 24, 2010
    Inventors: Lilian Monahan, Philip John Double, Roy Bradbury, Lynn Patricia Bradbury
  • Patent number: 7708824
    Abstract: 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: Grant
    Filed: June 4, 2007
    Date of Patent: May 4, 2010
    Assignee: DIC Corporation
    Inventors: Akihiro Ogata, Nagatoshi Kobayashi, Keiko Otsubo
  • Publication number: 20090294762
    Abstract: 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: Application
    Filed: April 28, 2009
    Publication date: December 3, 2009
    Inventors: Hyoyoung Lee, Junghyun Lee, Heeyoel Baek, Gyeong Sook Bang, Jonghyurk Park, Nak-Jin Choi, Kun Jun, Seung Rim Shin
  • Patent number: 7521545
    Abstract: 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: Grant
    Filed: August 25, 2005
    Date of Patent: April 21, 2009
    Assignee: Takeda Pharmaceutical Company Limited
    Inventors: Tomomi Ikemoto, Takeshi Yamasaki
  • Patent number: 7439339
    Abstract: 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: Grant
    Filed: April 19, 2005
    Date of Patent: October 21, 2008
    Assignee: Eastman Kodak Company
    Inventor: Catherine Mineur
  • Patent number: 7402369
    Abstract: 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: Grant
    Filed: September 29, 2006
    Date of Patent: July 22, 2008
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Masaki Okubo, Hideyuki Otsuka, Kazuo Nemoto, Masami Ito, Eisuke Yamada
  • Publication number: 20080161545
    Abstract: 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: Application
    Filed: December 12, 2005
    Publication date: July 3, 2008
    Inventors: Robert Egli, Thomas Grabenstein
  • Patent number: 7074906
    Abstract: 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: Grant
    Filed: November 26, 2002
    Date of Patent: July 11, 2006
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Stephen Daniel Pastor, Joseph Suhadolnik, Deborah Judd, Mervin Gale Wood
  • Patent number: 6923856
    Abstract: 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: Grant
    Filed: November 8, 2001
    Date of Patent: August 2, 2005
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Iain Frank Fraser, Sharon Kathleen Wilson, Ian Alexander Macpherson
  • Patent number: 6913640
    Abstract: 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: Grant
    Filed: January 15, 2002
    Date of Patent: July 5, 2005
    Assignee: CIBA Specialty Chemicals
    Inventors: Philippe Bugnon, Carolin Sansonnens, Greig Chisholm
  • Patent number: 6913641
    Abstract: 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: Grant
    Filed: April 27, 2002
    Date of Patent: July 5, 2005
    Assignee: Clariant GmbH
    Inventors: Hans Joachim Metz, Uday T. Nabar, Frank Morgenroth, Chandrashekhar D. Patil, Sunil D. Deval
  • Patent number: 6902612
    Abstract: 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: Grant
    Filed: September 8, 2003
    Date of Patent: June 7, 2005
    Assignee: Engelhard Corporation
    Inventor: Amrit P. Bindra
  • Patent number: 6756486
    Abstract: 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: Grant
    Filed: September 18, 2003
    Date of Patent: June 29, 2004
    Assignee: Engelhard Corporation
    Inventors: Amrit P. Bindra, Steven A. Zamborsky
  • Patent number: 6756485
    Abstract: 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−: the
    Type: Grant
    Filed: February 11, 2003
    Date of Patent: June 29, 2004
    Assignee: Orient Chemical Industries, Ltd.
    Inventors: Masashi Yasumatsu, Akihiro Tada, Shun-ichiro Yamanaka
  • Patent number: 6706863
    Abstract: 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: Grant
    Filed: August 15, 2002
    Date of Patent: March 16, 2004
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Isao Hashimoto, Noboru Tsuda, Hiroshi Ohsawa, Tomonori Okazaki, Manabu Shiga, Kohei Ohtsuki
  • Patent number: 6576748
    Abstract: 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: Grant
    Filed: June 27, 2002
    Date of Patent: June 10, 2003
    Assignee: Xerox Corporation
    Inventors: Rina Carlini, James D. Mayo, James M. Duff, Jeffrey H. Banning, Paul F. Smith, George Liebermann, Roger E. Gaynor
  • Patent number: 6566507
    Abstract: 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: Grant
    Filed: May 31, 2001
    Date of Patent: May 20, 2003
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Mervin G. Wood, Deborah DeHessa, Joseph Suhadolnik, Andrew B. Naughton, Jerome Sanders, Jacqueline Lau, Rong Xiong, Joseph Babiarz
  • Publication number: 20030054281
    Abstract: A dye-forming method comprising: reacting a dye-forming coupler and a color developing agent precursor represented by the following general formula (I): 1
    Type: Application
    Filed: November 14, 2001
    Publication date: March 20, 2003
    Inventors: Kensuke Morita, Shun-ichi Ishikawa, Hideaki Naruse, Koki Nakamura, Toshio Kawagishi, Tadashi Ohmatsu, Kozo Aoki
  • Patent number: 6375733
    Abstract: 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: Grant
    Filed: August 28, 2000
    Date of Patent: April 23, 2002
    Assignee: Engelhard Corporation
    Inventor: Amrit P. Bindra
  • Patent number: 6281338
    Abstract: 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: Grant
    Filed: September 19, 2000
    Date of Patent: August 28, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Richard Sommer, Frank Linke, Udo Herrmann
  • Patent number: 6254671
    Abstract: 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: Grant
    Filed: November 15, 1999
    Date of Patent: July 3, 2001
    Assignee: Engelhard Corporation
    Inventor: Byron G. Hays
  • Patent number: 6235100
    Abstract: 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: Grant
    Filed: June 24, 1999
    Date of Patent: May 22, 2001
    Assignee: Engelhard Corporation
    Inventor: Byron G. Hays
  • Patent number: 6150509
    Abstract: A water-insoluble yellow monoazo pigment has the following formula (I): ##STR1##
    Type: Grant
    Filed: November 12, 1999
    Date of Patent: November 21, 2000
    Assignee: Dominion Colour Corporation
    Inventors: Alan Gray, Henry Lui, Dorothy-Grace Manarang
  • Patent number: 6133432
    Abstract: 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: Grant
    Filed: December 1, 1998
    Date of Patent: October 17, 2000
    Assignee: Rhone-Poulenc Agro
    Inventors: David William Hawkins, David Alan Roberts, John Harry Wilkinson, Jean-Louis Clavel
  • Patent number: 6111083
    Abstract: 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: Grant
    Filed: April 20, 1999
    Date of Patent: August 29, 2000
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Antoine Clement, Alfons Arquint, Urs Lauk
  • Patent number: 6090927
    Abstract: 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: Grant
    Filed: February 16, 1999
    Date of Patent: July 18, 2000
    Assignee: Rhone-Poulenc Inc.
    Inventor: Peter Wyatt Newsome
  • Patent number: 6028178
    Abstract: 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: Grant
    Filed: July 26, 1999
    Date of Patent: February 22, 2000
    Assignee: Clariant GmbH
    Inventors: Hans Joachim Metz, Rudiger Baur, Hans-Tobias Macholdt
  • Patent number: 5998592
    Abstract: 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: Grant
    Filed: August 17, 1998
    Date of Patent: December 7, 1999
    Assignee: BASF Aktiengesellschaft
    Inventor: Nigel Hall
  • Patent number: 5973126
    Abstract: 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: Grant
    Filed: May 20, 1998
    Date of Patent: October 26, 1999
    Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo
    Inventors: Ryuzo Ueno, Masaya Kitayama, Kenji Minami, Hiroyuki Wakamori
  • Patent number: 5964899
    Abstract: Azo dyes containing sulphur dye entities as a constitutional component are dyes of valuable properties, in particular for the dyeing of leather.
    Type: Grant
    Filed: October 8, 1997
    Date of Patent: October 12, 1999
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Jordi Berenguer, Manuel Jose Domingo, Jose Rocas
  • Patent number: 5942604
    Abstract: 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: Grant
    Filed: February 20, 1998
    Date of Patent: August 24, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Paul Herzig, Antoine Clement, Romeo Dreier, Alfons Arquint
  • Patent number: 5889162
    Abstract: 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: Grant
    Filed: August 10, 1998
    Date of Patent: March 30, 1999
    Assignee: Engelhard Corporation
    Inventor: Byron G. Hays
  • Patent number: 5869628
    Abstract: 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: Grant
    Filed: August 26, 1997
    Date of Patent: February 9, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Paul Herzig, Antoine Clement
  • Patent number: 5852179
    Abstract: 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: Grant
    Filed: May 27, 1998
    Date of Patent: December 22, 1998
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Gregory Paul Dado
  • Patent number: 5824117
    Abstract: 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: Grant
    Filed: June 28, 1996
    Date of Patent: October 20, 1998
    Assignee: Dystar Japan Ltd.
    Inventors: Ulrich Buhler, Jurgen Kuhlwein, Hubert Kruse
  • Patent number: 5770708
    Abstract: 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: Grant
    Filed: May 27, 1997
    Date of Patent: June 23, 1998
    Assignee: BASF Aktiengesellschaft
    Inventor: Rudolf Bermes
  • Patent number: 5747566
    Abstract: 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: Grant
    Filed: August 8, 1996
    Date of Patent: May 5, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Joachim Weber
  • Patent number: 5744588
    Abstract: 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: Grant
    Filed: October 9, 1996
    Date of Patent: April 28, 1998
    Assignee: DyStar Japan Ltd.
    Inventors: Kiyoshi Himeno, Toshio Hihara, Yousuke Takahashi
  • Patent number: 5697985
    Abstract: 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: Grant
    Filed: May 24, 1996
    Date of Patent: December 16, 1997
    Assignee: Bayer Corporation
    Inventors: James J. Good, Tanya T. Harper, Samuel S. Murphree, John G. Skabardonis
  • Patent number: 5677435
    Abstract: 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: Grant
    Filed: September 24, 1996
    Date of Patent: October 14, 1997
    Assignee: Engelhard Corporation
    Inventor: Amrit Bindra