Formation Of Azo Group By Simultaneous Diazotization And Coupling Patents (Class 534/579)
  • Patent number: 9359503
    Abstract: An azo pigment or a tautomer thereof represented by the following Formula (1), and having characteristic X-ray diffraction peaks at Bragg angles (2?±0.2°) of 6.5°, 7.1° and 21.8° in the CuK? characteristic X-ray diffraction.
    Type: Grant
    Filed: January 28, 2014
    Date of Patent: June 7, 2016
    Assignee: FUJIFILM Corporation
    Inventors: Keiichi Tateishi, Shinya Hayashi, Hiroshi Yamada, Yoshiaki Nagata
  • Patent number: 9359502
    Abstract: There is provided a pigment dispersion including an azo pigment or a tautomer thereof represented by the following Formula (1) and having characteristic X-ray diffraction peaks at Bragg angles (2?±0.2°) of 4.8°, 7.2° and 9.7° in a CuK? characteristic X-ray diffraction.
    Type: Grant
    Filed: January 27, 2014
    Date of Patent: June 7, 2016
    Assignee: FUJIFILM Corporation
    Inventors: Keiichi Tateishi, Shinya Hayashi, Hiroshi Yamada, Yoshiaki Nagata
  • Patent number: 8834620
    Abstract: Black disazo dyes of general formula (V) wherein A is a moiety of formula (VI) or of formula (VII) and B is a moiety of formula (VII) or of formula (IX) and wherein M, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, R23, and R24, are as defined in the specification, are excellent black dyes for dying and printing cellulose containing materials and textile materials and, in particular, for preparation of recording liquids for ink jet printing and for writing utensils.
    Type: Grant
    Filed: October 17, 2011
    Date of Patent: September 16, 2014
    Assignee: Ilford Imaging Switzerland GmbH
    Inventors: Kurt Baettig, Jean-Luc Gremaud, Damien Moigno
  • Publication number: 20120090503
    Abstract: Black disazo dyes of general formula (V) wherein A is a moiety of formula (VI) or of formula (VII) and B is a moiety of formula (VIII) or of formula (IX) and wherein M, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, R23 and R24 are as defined in the specification, are excellent black dyes for dying and printing cellulose containing materials and textile materials and, in particular, for the preparation of recording liquids for ink jet printing and for writing utensils.
    Type: Application
    Filed: October 17, 2011
    Publication date: April 19, 2012
    Inventors: Kurt BAETTIG, Jean-Luc Gremaud, Damien Moigno
  • Patent number: 8137416
    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: April 2, 2007
    Date of Patent: March 20, 2012
    Assignee: Clariant Finance (BVI) Limited
    Inventor: Rainer Nusser
  • Patent number: 8088182
    Abstract: The present invention relates to dyes of formula wherein D, R1, R2, R3, R4 and n are defined as in the claims, to the process for the preparation thereof and to the use thereof in dyeing or printing semi-synthetic and especially synthetic hydrophobic textile materials, more especially textile materials.
    Type: Grant
    Filed: September 23, 2009
    Date of Patent: January 3, 2012
    Assignee: Huntsman International LLC
    Inventors: Ralf Petermann, Christian Suppiger, Urs Lauk
  • Publication number: 20110245475
    Abstract: There is provided an azo pigment having excellently good color reproducibility, dispersibility, and storage stability of pigment dispersions and having excellent hue and tinctorial strength. An azo pigment represented by the following formula (1) and having characteristic peaks at Bragg angles (2?±0.2°) of 7.2°, 13.4°, 15.0°, and 25.
    Type: Application
    Filed: December 8, 2009
    Publication date: October 6, 2011
    Applicant: FUJIFILM Corporation
    Inventors: Keiichi Tateishi, Yoshiaki Nagata, Shinya Hayashi
  • Publication number: 20110203058
    Abstract: Compounds of the general formula (I) a process for their preparation and their use for dyeing and/or printing organic substrates.
    Type: Application
    Filed: May 3, 2011
    Publication date: August 25, 2011
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Rainer NUSSER, Urs DÄETWYLER
  • 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: 7909891
    Abstract: The invention relates to a dye of the general formula (I) where D is the residue of a diazo component; R1 is hydrogen, (C1-C6-alkyl, (C1-C4)-alkoxy, hydroxyl, halogen, —NHCHO, —NHCO(C1-C6)-alkyl, —NHCOaryl, —NHSO2(C1-C6)-alkyl or —NHSO2aryl; R2 is hydrogen, (C1-C6)-alkyl, (C1-C4)-alkoxy, phenoxy or halogen; R3 is hydrogen, (C1-C6)-alkyl, substituted (C1-C6)-alkyl, (C3-C4)-alkenyl or substituted (C3-C4)-alkenyl; or R2 and R3 combine to form the radical —C*H(CH3)CH2C(CH3)2—, where the carbon atom marked * is attached to the phenyl nucleus; R4 is hydrogen, (C1-C6)-alkyl or phenyl; R5 is vinyl or a group of the formula —CHR6COR7, where R6 is hydrogen, (C1-C6)-alkyl or phenyl; R7 is (C1-C6)-alkyl, substituted (C1-C6)-alkyl, phenyl or substituted phenyl; and X is C1-C5)-alkylene. The invention for relates to a process to prepare the dye and their use.
    Type: Grant
    Filed: September 15, 2008
    Date of Patent: March 22, 2011
    Assignee: DyStar Colours Deutschland GmbH
    Inventor: Stefan Neubauer
  • Publication number: 20110023753
    Abstract: To provide an azo pigment composition having extremely good hue and extremely good light fastness and showing excellent tinctorial strength (color density) and, preferably, to provide an azo pigment composition further containing an azo pigment having characteristic X-ray diffraction peaks at different positions or a tautomer thereof. An azo pigment composition which contains at least one azo pigment represented by the following formula (1) and having characteristic peaks at Bragg angles (2?±0.2°) of 7.2° and 25.
    Type: Application
    Filed: March 5, 2009
    Publication date: February 3, 2011
    Applicant: FUJIFILM CORPORATION
    Inventor: Keiichi Tateishi
  • Publication number: 20110017099
    Abstract: To provide an azo pigment composition exhibiting very good hue and light fastness and having excellent tinctorial strength (color density) and preferably further provide an azo pigment composition containing an azo pigment having characteristic X-ray diffraction peaks at different positions or a tautomer thereof. An azo pigment composition comprising at least one kind of an azo pigment represented by formula (1) having characteristic X-ray diffraction peaks at Bragg angles) (2?±0.2°) of 7.6°, 25.6° and 27.
    Type: Application
    Filed: March 5, 2009
    Publication date: January 27, 2011
    Applicant: FUJIFILM CORPORATION
    Inventors: Keiichi Tateishi, Shinya Hayashi
  • Publication number: 20100233443
    Abstract: Compounds of the general formula (I) a process for their preparation and their use for dyeing and/or printing organic substrates.
    Type: Application
    Filed: June 21, 2007
    Publication date: September 16, 2010
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventor: Rainer Nusser
  • 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
  • Patent number: 7682406
    Abstract: The invention relates to novel dyes of the formula (1) in which D represents a phenyl or naphthalene residue which is substituted by one or two sulphonic Acid or carboxylic acid groups and, optionally, by one or two groups selected from C1-C4alkyl, hydroxyl and nitro, each R1 and R2, independently, represent hydrogen or, a C1-C4alkyl group, R?1 represents hydrogen, hydroxyl, C1-C4alkyl or C1-C4hydroxyalkyl, R3 represents hydrogen, C1-C4alkyl or phenyl, which is unsubstituted or substituted by one or two groups selected from C1-C4alkyl, C1-C4alkoxy, halogen, hydroxyl, —NH2, nitro, —SO3M and —CO2M and M represents hydrogen, an alkaline or alkaline earth metal, ammonium or ammonium that is mono-, di-, tri- or tetrasubstituted by C1-C4alkyl or C2-C4hydroxyalkyl or a polyglycolammonium cation and also known dyes of formula (5), in which D? represents a phenyl or naphthalene residue which is substituted by one or two sulphonic acid or carboxylic acid groups and, optionally, by one or two groups selected from C1-C4a
    Type: Grant
    Filed: June 26, 2006
    Date of Patent: March 23, 2010
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Adolf Käser, Wolfgang Schlenker
  • Patent number: 7649026
    Abstract: Radiation curable compositions, such as UV curable ink compositions, contain a polymeric dispersant, a curable material, and a nanoscale pigment particle composition including an organic monoazo laked pigment including at least one functional moiety, and a sterically bulky stabilizer compound including at least one functional group, wherein the functional moiety of the pigment associates non-covalently with the functional group of the stabilizer; and the presence of the associated stabilizer limits the extent of particle growth and aggregation, to afford nanoscale-sized pigment particles.
    Type: Grant
    Filed: November 1, 2007
    Date of Patent: January 19, 2010
    Assignee: Xerox Corporation
    Inventors: C. Geoffrey Allen, Rina Carlini, Sandra J. Gardner
  • Patent number: 7563318
    Abstract: A process for preparing nanoscale azo pigment particles includes providing an organic pigment precursor that contains at least one functional moiety, providing a sterically bulky stabilizer compound that contains at least one functional group, and carrying out a chemical reaction to form a pigment composition in a microreactor or micromixer, whereby the functional moiety found on the pigment precursor is incorporated within the pigment and non-covalently associated with the functional group of the stabilizer, so as to allow the formation of nanoscale-sized pigment particles and the production of such in a microreactor under laminar or turbulent flow conditions without clogging.
    Type: Grant
    Filed: July 2, 2008
    Date of Patent: July 21, 2009
    Assignee: Xerox Corporation
    Inventors: Santiago Faucher, Rina Carlini, Emily L. Moore, Christine M. Thompson, Sandra J. Gardner, Paul J. Gerroir, C. Geoffrey Allen
  • Publication number: 20090126128
    Abstract: Compounds of the general formula (I) a process for their preparation and their use for dyeing and/or printing organic substrates.
    Type: Application
    Filed: May 11, 2007
    Publication date: May 21, 2009
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Rainer Nusser, Urs Datwyler
  • Publication number: 20090083913
    Abstract: The invention relates to novel dyes of the formula (1) in which D represents a phenyl or naphthalene residue which is substituted by one or two sulphonic Acid or carboxylic acid groups and, optionally, by one or two groups selected from C1-C4alkyl, hydroxyl and nitro, each R1 and R2, independently, represent hydrogen or, a C1-C4alkyl group, R?1 represents hydrogen, hydroxyl, C1-C4alkyl or C1-C4hydroxyalkyl, R3 represents hydrogen, C1-C4alkyl or phenyl, which is unsubstituted or substituted by one or two groups selected from C1-C4alkyl, C1-C4alkoxy, halogen, hydroxyl, —NH2, nitro, —SO3M and —CO2M and M represents hydrogen, an alkaline or alkaline earth metal, ammonium or ammonium that is mono-, di-, tri- or tetrasubstituted by C1-C4alkyl or C2-C4hydroxyalkyl or a polyglycolammonium cation and also known dyes of formula (5), in which D? represents a phenyl or naphthalene residue which is substituted by one or two sulphonic acid or carboxylic acid groups and, optionally, by one or two groups selected from C1-C4a
    Type: Application
    Filed: June 26, 2006
    Publication date: April 2, 2009
    Inventors: Adolf Kaser, Wolfgang Schlenker
  • Patent number: 7473310
    Abstract: A nanoscale pigment particle composition includes an organic monoazo laked pigment including at least one functional moiety, and a sterically bulky stabilizer compound including at least one functional group, wherein the mono-azo laked pigment includes a nono-azo dye molecule laked with a divalent metal cation; the functional moiety associates non-covalently with the functional group; and the presence of the associated stabilizer limits the extent of particle growth and aggregation, to afford nanoscale-sized pigment particles. Non-aqueous dispersion compositions, such as ink compositions, contain a polymeric dispersant, an organic liquid, and the nanoscale pigment particle composition.
    Type: Grant
    Filed: December 21, 2007
    Date of Patent: January 6, 2009
    Assignee: Xerox Corporation
    Inventors: Rina Carlini, Jeffrey H. Banning, C. Geoffrey Allen, Sandra J. Gardner, Jonathan Siu-Chung Lee
  • Patent number: 7465348
    Abstract: A nanoscale pigment particle composition includes an organic monoazo laked pigment including at least one functional moiety, and a sterically bulky stabilizer compound including at least one functional group, wherein the functional moiety associates non-covalently with the functional group; and the presence of the associated stabilizer limits the extent of particle growth and aggregation, to afford nanoscale-sized pigment particles.
    Type: Grant
    Filed: June 7, 2007
    Date of Patent: December 16, 2008
    Assignee: Xerox Corporation
    Inventors: Rina Carlini, C. Geoffrey Allen, Sandra J. Gardner, Karl W. Dawson, Peter G. Odell, Paul F. Smith, Jennifer L. Belelie
  • Patent number: 7465349
    Abstract: A nanoscale pigment particle composition includes an organic monoazo laked pigment including at least one functional moiety, and a sterically bulky stabilizer compound including at least one functional group, wherein the functional moiety associates non-covalently with the functional group; and the presence of the associated stabilizer limits the extent of particle growth and aggregation, to afford nanoscale-sized pigment particles.
    Type: Grant
    Filed: November 1, 2007
    Date of Patent: December 16, 2008
    Assignee: Xerox Corporation
    Inventors: Rina Carlini, Karl W. Dawson, Sandra J. Gardner, C. Geoffrey Allen
  • Patent number: 6989055
    Abstract: A monoazo lake pigment composition containing a monoazo lake pigment obtained from a laked pigment aqueous slurry prepared by conducting coupling of a diazo component obtained by diazotizing an aromatic amine having a soluble group and a coupler component and conducting laking after or simultaneously with the coupling, wherein the laking is carried out in the presence of a water-soluble acrylic polymer in an amount of 0.1 to 40 parts by weight per 100 parts of the above coupler component, and a gravure ink containing the above pigment composition and a gravure ink vehicle.
    Type: Grant
    Filed: August 6, 2003
    Date of Patent: January 24, 2006
    Assignee: Toyo Ink Mfg. Co., Ltd.
    Inventors: Kenji Kitamura, Shigeki Kato, Hitoshi Maki, Shoko Goto, Motoi Shitaka, Osamu Shiromaru
  • Patent number: 6872245
    Abstract: This invention relates to azo pigments of general formula (I) wherein D represents the radical of a diazo component; R1 and R2 are the same or different and represent hydrogen, a C1-C4 alkyl radical which is optionally substituted by hydroxy, amino, halogen or methoxy, or a (C6-C10) aryl radical which is optionally substituted by one, two or three substituents from the group C1-C4 alkyl, C1-C4 alkoxy, F, Cl, Br, CF3, NO2, OH, CONH2, CONH(C1-C4 alkyl), CON(C1-C4 alkyl)2, COO(C1-C4 alkyl), SO2NH2, SO2NH(C1-C4 alkyl) and SO2N(C1-C4 alkyl)2, provided that R1 and R2 do not simultaneously represent hydrogen; R4 represents hydrogen, C1-C4 alkyl, halogen, trifluoromethyl, C1-C4 alkoxy, NO2, or CN; and n represents 1, 2 or 3
    Type: Grant
    Filed: July 24, 2002
    Date of Patent: March 29, 2005
    Assignee: Clariant GmbH
    Inventors: Felix W. Grimm, Hans Joachim Metz, Andreas Wacker
  • Patent number: 6780427
    Abstract: SOD and other active oxygen inhibitors are directly applied in combination with a barrier material at local sites of tissue injury to prevent or decrease formation of adhesions and undesirable proliferation of cells. Preferred barrier materials are polymeric hydrogels providing controlled release of AOI which are directly applied to the afflicted tissue. Examples demonstrate the effects of SOD on pelvic adhesions in the rat when administered by intraperitoneal (I.P.) bolus and by localized sustained release from a topically applied hydrogel system.
    Type: Grant
    Filed: July 27, 1998
    Date of Patent: August 24, 2004
    Assignee: Genzyme Corporation
    Inventors: Keith Baker, Arthur J. Coury
  • Patent number: 6504045
    Abstract: The invention relates to six new crystal polymorphs, &agr; (alpha), &bgr; (beta), &ggr; (gamma), &dgr; (delta), &zgr; (zeta), and &eegr; (eta), of the disazo colorant of the formula I, having characteristic reflections in the X-ray diffraction spectrum. The novel crystal polymorphs are prepared by treatment in organic solvents.
    Type: Grant
    Filed: September 13, 2001
    Date of Patent: January 7, 2003
    Assignee: Clariant GmbH
    Inventors: Ruediger Jung, Hans-Joachim Metz, Joachim Weber, Martin U. Schmidt, Olaf Schupp, Andreas Wacker
  • Publication number: 20020188112
    Abstract: A method for the production of diazomethane comprising the steps of a) feeding a base and a diazomethane precursor into a reactor vessel; b) generating gaseous diazomethane by allowing the base and the gaseous diazomethane precursor to react; and c) removing the gaseous diazomethane using a diluent gas.
    Type: Application
    Filed: May 2, 2002
    Publication date: December 12, 2002
    Inventors: Antony John Warr, Lee Proctor
  • Publication number: 20020128452
    Abstract: There is provided a process for the production of a compound of formula I, 1
    Type: Application
    Filed: March 28, 2001
    Publication date: September 12, 2002
    Inventors: Jorgen Alvhall, Daniel Edvardsson, Panagiotis Ioannidis, Magnus Sjogren, Maria Szonyi
  • Publication number: 20020055619
    Abstract: The invention provides a process for preparing azo colorants which comprises spraying one or more coupling components individually or in a mixture and one or more compatible diazonium salts individually or in a mixture, in their solution or suspension form through nozzles to a point of conjoint collision in a reactor chamber enclosed by a housing in a microjet reactor, a gas or an evaporating liquid being passed into the reactor chamber through an opening in the housing for the purpose of maintaining a gas atmosphere in the reactor chamber, and the resulting product solution or suspension and the gas or the evaporated liquid being removed from the reactor through a further opening in the housing by means of overpressure on the gas entry side or underpressure on the product and gas exit side.
    Type: Application
    Filed: October 5, 2001
    Publication date: May 9, 2002
    Applicant: Clariant GmbH
    Inventors: Erwin Dietz, Joachim Weber, Dieter Schnaitmann, Christian Wille, Leonhard Unverdorben, Klaus Saitmacher, Jorg Jung, Kristina Schiffer
  • Patent number: 5746821
    Abstract: Disclosed are compositions comprising one or more compounds characterized by the formula: ##STR1## wherein Ar is an aromatic moiety having at least one substituent which is an acid group or salt thereof; X is a hydrocarbyl, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide or sulfonic acid amide group; each Y is independently a hydrocarbyl, halogen, hydrocarbyloxy, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide, imidazolone, sulfonic acid amide or nitro group; and a is 1, 2 or 3. Also disclosed is a process for preparing azo dyes which comprises coupling (i) at least one diazonium component of one or more aromatic amines containing at least one sulfonic acid group or carboxylic acid group, or salts thereof; with (ii) at least one coupling component represented by the formula: ##STR2## wherein X, Y and a are as defined above. The dye compositions prepared by this process and the azo pigments derived from such dyes are also disclosed.
    Type: Grant
    Filed: February 13, 1995
    Date of Patent: May 5, 1998
    Assignee: Engelhard Corporation
    Inventor: Byron G. Hays
  • 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: 5606034
    Abstract: The invention discloses a process for the preparation of azo dyes using an aminodiphenylamine as diazo component. The process comprises reacting the amine, an alkali metal nitrite and a mineral acid continuously in the temperature range from 35.degree. to 65.degree. C. to give the diazo compound, using a 3 to 15% excess of alkali metal nitrite, and thereafter coupling the diazo compound to a coupling component. Azo dyes of superior quality constancy and in high yield are obtained by the novel process.
    Type: Grant
    Filed: February 16, 1995
    Date of Patent: February 25, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Horst Langfeld, Karl-Friedrich Haarburger, Herbert Mauser
  • Patent number: 5578711
    Abstract: Dyestuffs of the formula ##STR1## in which D is the radical of an aromatic or heterocyclic diazo component andK is the radical of an aromatic or heterocyclic coupling component, or is the radical of an active methylene compound,are obtained in an ecologically advantageous manner by reacting an aromatic or heterocyclic diazo components of the formulaD--NH.sub.2and a coupling component of the formulaH--Kwith a nitrite, for example NaNO.sub.2, in the presence of CO.sub.2 at a pressure of 5-100 at. The process is suitable in particular for the preparation of concentrated dye-stuff solutions, because expensive operations, such as, for example, pressure permeation and reverse osmosis, can be omitted.
    Type: Grant
    Filed: September 14, 1995
    Date of Patent: November 26, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Roderich Raue, Alfred Brack, Karl-Heinrich Lange
  • Patent number: 5559216
    Abstract: An ecologically and economically advantageous process for preparing a disazo pigment of the formula (I) or a mixture of said disazo pigments ##STR1## where D.sup.1 and D.sup.2 are identical or different and each is unsubstituted phenyl, phenyl with from 1 to 5 substituents, unsubstituted naphthyl, naphthyl with from 1 to 3 substituents, unsubstituted anthraquinonyl, anthraquinonyl with from 1 to 3 substituents, or a radical of a fused aromatic heterocycle which contains from 1 to 3 identical or different heteroatoms from nitrogen or oxygen and sulfur and is unsubstituted or has from 1 to 3 substituents,R.sup.1 and R.sup.2 are identical or different and each is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.
    Type: Grant
    Filed: September 1, 1993
    Date of Patent: September 24, 1996
    Assignee: Hoechst AG
    Inventors: Ruediger Jung, Joachim Weide, Hans J. Metz
  • Patent number: 5541299
    Abstract: Dyestuffs of the formula ##STR1## in which D is the radical of an aromatic or heterocyclic diazo component andK is the radical of an aromatic or heterocyclic coupling component, or is the radical of an active methylene compound,are obtained in an ecologically advantageous manner by reacting an aromatic or heterocyclic diazo components of the formulaD--NH.sub.2and a coupling component of the formulaH--Kwith a nitrite, for example NaNO.sub.2, in the presence of CO.sub.2 at a pressure of 5-100 at. The process is suitable in particular for the preparation of concentrated dye-stuff solutions, because expensive operations, such as, for example, pressure permeation and reverse osmosis, can be omitted.
    Type: Grant
    Filed: September 23, 1994
    Date of Patent: July 30, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Roderich Raue, Alfred Brack, Karl-Heinrich Lange
  • Patent number: 5502171
    Abstract: Dyestuffs of the formula ##STR1## in which D is the radical of an aromatic or heterocyclic diazo component andZ is the radical of an aromatic or heterocyclic coupling component,are obtained in an ecologically advantageous manner by reacting an aromatic or heterocyclic diazo components of the formulaD--NH.sub.2and a coupling component of the formulaH--Z.sub.1with a nitrite, in the presence of CO.sub.2 at a pressure of 5-100 at. The process is suitable in particular for the preparation of concentrated dyestuff solutions, because expensive operations, such as, for example, pressure permeation and reverse osmosis, can be omitted.
    Type: Grant
    Filed: May 16, 1995
    Date of Patent: March 26, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Roderich Raue, Alfred Brack, Karl-Heinrich Lange
  • Patent number: 5360472
    Abstract: Disclosed are dye compositions of the formula ##STR1## wherein Cp and Cp' are each coupler compounds of the formula ##STR2## wherein the --COOH group and the --OH group can be in any position on either ring, provided that in the naphthalene ring system there is present least one hydrogen activated through resonance by the --OH group for an electrophilic aromatic substitution coupling reaction, n represents the number of substituents on the rings and is a number of from 0 to 8, and R represents the substituent groups on the ring, wherein each R is independently selected from the group consisting of hydroxyl groups, alkyl groups, substituted alkyl groups, aryl groups, substituted aryl groups, aryl-alkyl groups, substituted aryl-alkyl groups, halogen atoms, and nitro groups. Also disclosed are aqueous ink compositions containing the dyes, processes for making the dyes, processes for making the inks containing the dyes, and printing processes employing the inks.
    Type: Grant
    Filed: July 26, 1993
    Date of Patent: November 1, 1994
    Assignee: Xerox Corporation
    Inventors: Edward J. Radigan, Jr., Louis V. Isganitis, Warren E. Solodar, Kurt B. Gundlach
  • Patent number: 5194597
    Abstract: The industrial preparation of C.I. Pigment Yellow 81 by conventional coupling methods has the disadvantage that traces of polychlorinated biphenyls are formed in the course of the reaction of the two components.The invention now provides that the addition of quaternary dialkyldiallylammonium compounds during the azo coupling will decisively suppress the PCB-forming secondary reactions during the pigment synthesis.
    Type: Grant
    Filed: April 30, 1991
    Date of Patent: March 16, 1993
    Assignee: Hoechst AG
    Inventor: Wolfgang Rieper
  • Patent number: 5162511
    Abstract: Sulfonic acids are reacted with sodium nitrite to form new compositions specifically nitrosyl sulfonates. The nitrosyl sulfonates are useful in reacting with a dye base to form a diazo composition which can in turn react with a coupling agent to form a diazo dye. The nitrosyl sulfonate can also be used to react with an aromatic composition to nitrosoate an aromatic composition. These reactions are particularly useful in the formation of a dispersed dye because the dye can be formed directly in a nonpolar organic solvent and can be used without purification of the dye product. Particularly useful is the nitrosyl dodecyl benzene sulfonate since the formed product is soluble in nonpolar solvents and all reaction products remain in solution and aid with the dyeing of fabrics.
    Type: Grant
    Filed: March 27, 1992
    Date of Patent: November 10, 1992
    Inventor: Rodger L. Gamblin
  • Patent number: 5086168
    Abstract: The invention relates to monoazo pigments prepared from dichloroanilines as diazo components and CH-acidic coupling components of the acetoacetarylamide or naphthol series, these pigments only containing an extremely low level of polychlorinated biphenyls (PCBs) (at most 25 .mu.g per g of pigment).The process for preparing the pigments takes the form of an azo coupling in an aqueous medium, whereina) azo coupling is effected by adding the diazonium salt solution to a suspension or solution of the coupling component or by simultaneously metering the aqueous suspensions or solutions of the diazonium salt and of the coupling component into the reaction mixture,b) azo coupling is effected at a pH or within a pH range of less than pH 7 andb1) between pH 4 and 7 during and after azo coupling less than 0.
    Type: Grant
    Filed: September 5, 1990
    Date of Patent: February 4, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Wolfgang Rieper
  • Patent number: 5024698
    Abstract: Monoazo pigments are provided which have improved properties achieved by incorporating certain azomethine compounds. The pigment compositions are prepared by reacting a primary amine-terminated alkylene oxide polymer and an acetoacetanilide to form an azomethine coupler and subsequently preparing the monoazo pigment composition by reacting the desired diazo component and coupling component in the presence of the azomethine coupler so as to form an azomethine composition of matter and the desired pigment.
    Type: Grant
    Filed: March 22, 1990
    Date of Patent: June 18, 1991
    Assignee: Sun Chemical Corporation
    Inventors: Russell J. Schwartz, Manuel Z. Gregorio
  • Patent number: 4985045
    Abstract: A monoazo dyestuff composition comprising at least two different individual compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2, independently of each other, are linear or branched alkyl having 1 to 4 carbon atoms and R is linear or branched alkyl having 1 to 5 carbon atoms, and where said individual compounds differ from each other in at least the R moiety, has improved dyeing properties compared with the individual dyestuffs when used to dye or print hydrophobic fiber materials.
    Type: Grant
    Filed: October 30, 1989
    Date of Patent: January 15, 1991
    Assignee: Cassella Aktiengesellschaft
    Inventors: Ulrich Buhler, Klaus Hofmann
  • Patent number: 4980459
    Abstract: The invention describes a process for the preparation of formulations of water-insoluble to sparingly soluble azo dyes by simultaneous diazotization and coupling in a single step reaction, filtering the dye dispersion and, if desired, drying the dyestuff, which process comprises carrying out said simultaneous diazotization and coupling by intimately mixing the aqueous solution or suspension of the reactants, in the presence of one or more surface-active agents, concentrating the dilute dye dispersion by membrane separating methods, and at the same time at least partially removing salt and/or acid from the dispersion and converting it into a storage stable liquid formulation or, by drying, into a solid dye formulation.
    Type: Grant
    Filed: August 14, 1989
    Date of Patent: December 25, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Alberto Rabassa, Beat Bruttel
  • Patent number: 4925926
    Abstract: The invention relates to a continuous process for the preparation of cationic azo or hydrazone dyes from heterocyclic diazo components and coupling components. The diazo component is diazotised in water and an acid, the diazo solution is coupled with the coupling component and continuously alkylated, preferably using sufficient acid that, after the alkylation, a two-phase system forms, consisting of an aqueous solution which is substantially free from dye and a highly concentrated oil phase or solid dye.
    Type: Grant
    Filed: December 7, 1987
    Date of Patent: May 15, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Roland Ronco, Ermanno Ciapponi, Pierre Pessonneaux
  • Patent number: 4923972
    Abstract: Liquid formulations of basic azo dyes are prepared from unsubstituted or C.sub.1 -C.sub.4 -alkyl- or C.sub.1 -C.sub.4 -alkoxy-substituted m-phenylenediamine by diazotizing and coupling in carboxylic acid solution, which comprises performing the reaction with 0.76 to 0.95 mole of nitrile, calculated as nitrous acid and based on 1 mole of m-phenylenediamine, and then heating the resulting reaction mixture at from 60.degree. C. to the boiling point of the reaction mixture.
    Type: Grant
    Filed: April 14, 1988
    Date of Patent: May 8, 1990
    Assignee: BASF Aktiengesellschaft
    Inventor: Karl Schmeidl
  • Patent number: 4921945
    Abstract: Disazo dyes which are useful for dyeing and printing, of the formula ##STR1## in which: D is the radical of a substituted or unsubstituted, homocyclic or heterocyclic diazo component, V.sup.1 and V.sup.2 independently of one another are hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, halogen or cyano, X is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, halogen, cyano or a group of the formula --NH--CHO, --NH--CO--NH.sub.2, --NH--CO--NH--Q or --NH--CO--(0).sub.m --Q in which m is zero or 1 and Q is substituted or unsubstituted C.sub.1 -C.sub.4 alkyl or phenyl, Z is C.sub.1 -C.sub.4 alkyl--CO--, --CN, --COO--C.sub.1 -C.sub.4 alkyl, --CONH.sub.2 or --CO--C.sub.6 H.sub.5, R.sup.1, R.sup.2 and R.sup.3 independently of one another are in each case a substituted or unsubstituted alkyl radical or R.sup.1 and R.sup.2, together with the nitrogen atom linking them, or R.sup.1, R.sup.2 and R.sup.
    Type: Grant
    Filed: May 25, 1988
    Date of Patent: May 1, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Willy Stingelin
  • Patent number: 4918168
    Abstract: Disclosed is a process for continuous preparation of aromatic diazonium fluoride salts wherein diazotizable aromatic primary amines are continuously diazotized in a reactor containing a plurality of sequential reaction zones, wherein a portion of the diazotization agent is continuously injected into each of the reaction zones.
    Type: Grant
    Filed: November 24, 1987
    Date of Patent: April 17, 1990
    Assignee: Mallinckrodt Inc.
    Inventors: Nickolas J. Stepaniuk, Bruce J. Lamb
  • Patent number: 4880916
    Abstract: Azo dyes of the formula ##STR1## or tautomers thereof, wherein Z is N,S or CH,X is O,S,NR.sup.2 or N, V is N or CH, W is N or C, K is a coupling component from the group consisting of acylacetarylamides, phenols, pyridones, quinolines, pyrazoles, indoles, diphenylamines, aminopyridines, pyrimidines, pyrimidones, naphthols, naphthylamines, aminoathiozoles, thiophenes and hydroxypyridines, R is unsubstituted or substituted alkyl or alkenyl, R.sup.1 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, nitro, --CN, --NHR.sup.2, --NH--acyl, phenoxy, --COOR.sup.2, --COOR.sup.2 --CONHR.sup.2 or substituted or unsubstituted phenyl, R.sup.2 is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.6 alkyl or substituted or unsubstituted phenyl, D is a 1,4-phenylene radical which can be substituted further and AN.THETA.
    Type: Grant
    Filed: March 24, 1988
    Date of Patent: November 14, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Jean-Marie Adam
  • Patent number: 4845638
    Abstract: The invention relates to an automatically controlled continuous method of eliminating excess nitrite in diazotization solutions of aromatic amines, which comprises controlling the addition of the agent employed for eliminating the nitrite ions by means of an electrochemically controlled variable.The process permits a smooth monitoring of the nitrite ion concentration in diazotization solutions. It is advantageous that the determination of the electrochemical controlled variable is almost instantaneous and that the addition of agent for removing nitrite ions can be controlled in simple manner via the fluctuations in the potential.
    Type: Grant
    Filed: July 8, 1986
    Date of Patent: July 4, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Ferenc Rakoczi, Bruno Fortsch
  • Patent number: 4791211
    Abstract: An improved process for the production of 2-stilbylnaphthotriazole optical bleaches which involves diazotizing aminostilbene 2-sulfonic acids, coupling the thus formed diazonium salt with naphthylamino-sulfonic acid to form the stilbylnaphthyl monoazo salt by adding the naphthylamino-sulfonic acid to the diazonium salt from the diazotization, neutralized to a pH in the range of 6-8, in the presence of 2-butoxyethanol, oxidizing said monoazo salt to form the 2-stilbylnaphthotriazole compounds with air in an aqueous alkaline medium containing butoxyethanol and isolating and recovering said 2-stilbylnaphotriazole optical bleaches as their sodium salts.
    Type: Grant
    Filed: January 20, 1987
    Date of Patent: December 13, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Richard B. Lund, Larry W. Bass