Metallization Of The Azo Reactant In Presence Of An Additional Organic Compound Patents (Class 534/602)
  • Patent number: 8932786
    Abstract: The new metal azo pigments comprising the adduct of a) at least two metal azo compounds of the formula (I) or their tautomeric forms in which the substituents have the definition indicated in the description, and b) at least one compound of the formula (II) in which R6 has the definition indicated in the description, are characterized in that in the X-ray diffractogram with a lattice constant of d=10.3 (±0.2) ? the metal azo pigment has a signal S1 with an intensity I1 and in the lattice constant range from d=16.05 ? to d=11.78 ? has no signal S2 whose intensity I2 in relation to the intensity I1 of signal S1, expressed as ratio I2/I1 of the background-corrected intensities, exceeds a value of 0.02, and are outstandingly suitable for producing pigment preparations and especially for producing color filters.
    Type: Grant
    Filed: July 2, 2013
    Date of Patent: January 13, 2015
    Assignee: LANXESS Deutschland GmbH
    Inventors: Hans-Ulrich Borst, Frank Linke, Heinz-Josef Fuellmann, Stephan Michaelis, Dirk Pfuetzenreuter, Sabine Endert
  • Publication number: 20140016072
    Abstract: The new metal azo pigments comprising the adduct of a) at least two metal azo compounds of the formula (I) or their tautomeric forms in which the substituents have the definition indicated in the description, and b) at least one compound of the formula (II) in which R6 has the definition indicated in the description, are characterized in that in the X-ray diffractogram with a lattice constant of d=10.3 (±0.2) ? the metal azo pigment has a signal S1 with an intensity I1 and in the lattice constant range from d=16.05 ? to d=11.78 ? has no signal S2 whose intensity I2 in relation to the intensity I1 of signal S1, expressed as ratio I2/I1 of the background-corrected intensities, exceeds a value of 0.02, and are outstandingly suitable for producing pigment preparations and especially for producing colour filters.
    Type: Application
    Filed: July 2, 2013
    Publication date: January 16, 2014
    Applicant: LANXESS Deutschland GmbH
    Inventors: Hans-Ulrich BORST, Frank LINKE, Heinz-Josef FUELLMANN, Stephan MICHAELIS, Dirk PFUETZENREUTER, Sabine ENDERT
  • Patent number: 8445651
    Abstract: The invention discloses a method for producing a charge control agent and a toner containing the charge control agent. The preparation method includes the technical proposal that in aqueous medium, an azo compound is reacted with a salicylic acid chromium complex, which is used as a complexing agent to synthesize a specific azo chromium complex. The preparation method is characterized by complex synthesis engineering. The toner of the invention includes a charge control agent obtained from the method described herein. Provided is a method for obtaining a charge control agent and a toner with excellent chargeability in that no flying or fogging is observed, even during image formation at high printing speeds. The toner is relatively free from the influences of variations in the environmental temperature and humidity, which ensures stable image printing with high picture quality for long periods of time.
    Type: Grant
    Filed: February 26, 2009
    Date of Patent: May 21, 2013
    Assignee: Hubei Dinglong Chemical Co., Ltd.
    Inventors: Shunquan Zhu, Yubin Wang
  • Publication number: 20110319604
    Abstract: The present invention relates to a method for preparing an MOF solid of a crystallised and porous aluminium aromatic azocarboxylate, in a non-aqueous organic medium. The invention also relates to solids made up of metal-organic frameworks (MOF) of aluminium aromatic azocarboxylates capable of being obtained by the method of the invention, as well as to the uses thereof for the storage of liquid or gaseous molecules, for selective separation of gas and for catalysis.
    Type: Application
    Filed: November 17, 2009
    Publication date: December 29, 2011
    Applicants: UNIVERSITE DE VERSAILLES-SAINT QUENTIN EN YVELINES, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE CNRS-
    Inventors: Thierry Loiseau, Gérard Ferey, Christophe Volkringer, Francis Taulelle, Mohamed Haouas
  • Patent number: 8076465
    Abstract: A method for manufacturing a charge control agent comprising steps of: an initiative chelating step by reacting with a monoazo compound represented by the following chemical formula [1] (in the chemical formula [1], —Ar1— and —Ar2— are aromatic groups) and a metal chelating agent to prepare an azo-type metal complex salt intermediate; a subsequent ion-exchanging step by reacting with the azo-type metal complex salt intermediate and an ammonium counter ion forming agent including an inorganic ammonium salt and aqueous ammonia to prepare an azo-type metal complex salt having an ammonium ion of a counter ion represented by the following chemical formula [2] (in the chemical formula [2], —Ar1— and —Ar2— are the same as the chemical formula [1]; M is a trivalent metal; B+ is a cation except an ammonium ion; n is from 0.70 to 1.00).
    Type: Grant
    Filed: October 7, 2004
    Date of Patent: December 13, 2011
    Assignee: Orient Chemicals Industries, Lt.
    Inventors: Kazuyoshi Kuroda, Masashi Yasumatsu, Osamu Yamate, Kaori Sato, Jun Hikata
  • Publication number: 20100105884
    Abstract: A method for producing a charge control agent or a toner containing the charge control agent comprising reacting in aqueous medium an azo compound with a salicylic acid chromium complex.
    Type: Application
    Filed: February 26, 2009
    Publication date: April 29, 2010
    Applicant: HUBEI DINGLONG CHEMICAL CO., LTD.
    Inventors: Shunquan ZHU, Yubin WANG
  • Patent number: 7132516
    Abstract: This invention relates to coppered azo dyestuffs containing an alkyl-, aryl or alkoxyalkyl sulfamyl group on one moiety of the molecule and an alkyl-, aryl or alkoxyalkyl ammonium sulfonate or carboxylate group on the other moiety. The invention also relates to various intermediates, to compositions and to processes for preparing the metalized dyestuffs. The compounds are particularly suited for the application in laquers, ink-jet inks and electrographic toners.
    Type: Grant
    Filed: January 29, 2003
    Date of Patent: November 7, 2006
    Assignee: Clariant Finance (BVI) Limited
    Inventor: Dominique Pflieger
  • Patent number: 6984724
    Abstract: The invention relates to novel monoazo compounds of formula (1), wherein R1 re resents H, Cl or CH3; R2 represents H or Cl; M2+ represents Mg2+, Mn2+ or Sr2+; Y1=represents COO? or SO3?; Y2=SO3?; Y3=Y4=Y5=H; or Y3=SO331 , Y2=Y4=Y5=H; or Y4=SO3?, Y2=Y3=Y5=H; or Y5=SO3?, Y2=Y3=Y4=H. The compounds of formula (1) are characterized by high intensity and light-fastness.
    Type: Grant
    Filed: July 27, 2002
    Date of Patent: January 10, 2006
    Assignee: Clariant GmbH
    Inventors: Hans Joachim Metz, Uday T. Nabar, Frank Morgenroth, Chandrashekhar D. Patil, Sunil D. Deval
  • 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: 6881830
    Abstract: Metal complexes of metals of the scandium group with an azo compound which conforms to the formula (I) or to one of its tautomeric structures where R is OH, NH2, NH—CN, arylamino or acylamino, R? is NH2, NH—CN, arylamino or acylamino and R1 and R1? are independently —OH or —NH2.
    Type: Grant
    Filed: March 25, 2003
    Date of Patent: April 19, 2005
    Assignee: Bayer Chemicals AG
    Inventors: Ulrich Feldhues, Frank Linke, Ronald Göbel, Udo Herrmann, Sabine Endert
  • Patent number: 6852135
    Abstract: Dyes of the general formula (1): where M is hydrogen, alkali, ammonium or the equivalent of an alkaline earth metal ion, X is halogen, alkoxy or an N-containing heterocycle, Q is a grouping of the formula (e) where Y is vinyl or an alkali-eliminable grouping and W is alkyl which may be interrupted by an O or an NR group and the radicals R1 and R2 represent alkyl, alkoxy, alkylcarbonylamino, arylcarbonylamino, and also the radicals R3 and R4 are alkyl or hydrogen, their preparation and their use for dyeing and printing hydroxyl- and/or carboxamido-containing material, preferably fiber material.
    Type: Grant
    Filed: July 14, 2001
    Date of Patent: February 8, 2005
    Assignee: DyStar Textilfarben GmbH & Co. Deutschland KG
    Inventors: Joachim Steckelberg, Hermann Henk
  • Patent number: 6784286
    Abstract: The invention relates to pyrazolone pigments of general formula (I), wherein the radicals R1, R2, R3 and R4 independently represent hydrogen, chlorine, methyl or ethyl, whereby at least one of the radicals R1-R4 is different from hydrogen. The inventive pigments are characterised by a CIELAB colour angle of 80-85°, a chroma of 58-62 and a luminosity ≧87 (measuring angle 45°, standard illuminant D65).
    Type: Grant
    Filed: June 13, 2003
    Date of Patent: August 31, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Blaschka, Günter Smeyts, Paul Günthert
  • 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: 6548648
    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: wherein the substituents are as defined in the disclosure.
    Type: Grant
    Filed: July 13, 2000
    Date of Patent: April 15, 2003
    Assignee: Orient Chemical Industries, Ltd.
    Inventors: Masashi Yasumatsu, Akihiro Tada, Shun-ichiro Yamanaka
  • Patent number: 6469147
    Abstract: Azo colorants are prepared by conducting the diazotization of aromatic or hetaromatic amines or the azo coupling reaction or the diazotization and the azo coupling reaction in a microreactor.
    Type: Grant
    Filed: February 9, 2001
    Date of Patent: October 22, 2002
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Uwe Nickel, Rüdiger Jung, Klaus Saitmacher, Leonhard Unverdorben
  • 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: 6350307
    Abstract: Metal complexes of an azo compound which conforms to the formula (I) or one of its tautomeric structures wherein R and R′ are independently OH, NH2, NH—CN, acylamino or arylamino, R1 and R1′ are independently —OH or —NH2, and which contain at least one guest compound, characterized in that the metal complexes correspond to the mono-, di-, tri- and tetrainions of the azo compounds of the formula (I) with the metals selected from the group consisting of Ca, Zn, Cu, Fe, Co, Sr, Ba, Cr, Sn, Al, Mg, Cd, Pb and La.
    Type: Grant
    Filed: October 8, 1999
    Date of Patent: February 26, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Frank Linke, Kent Faubion, Udo Herrmann, Richard Sommer
  • Patent number: 6302949
    Abstract: Metallized bisazo dyes of general formula (IX) or of general formula (X) wherein A, R1, R2, R3, M and Met are defined in the specification are excellent dyes for dying and printing cellulose containing materials and especially for the preparation of inks for ink jet printing.
    Type: Grant
    Filed: August 18, 1999
    Date of Patent: October 16, 2001
    Assignee: Ilford Imaging Switzerland GmbH
    Inventor: Heinz Peter
  • 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: 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: 5637678
    Abstract: The invention provides a process for the production of azodyes and their derivatives by diazotization and coupling reactions and optionally further modification reactions, wherein a compound of formula ##STR1## in which E signifies an aromatic bivalent radical,X.sub.1 signifies hydroxy or a primary amino group,Y.sub.1 signifies hydroxy or a primary amino group and in which the aminogroup linked to the --SO.sub.2 -bound phenyl radical may optionally be acylated,or a mixture of compounds of formula (I), is employed as a coupling component or/and--in the non-acylated form--as a diazo component,the invention in particular relates also to the novel dyes and their use and to the novel intermediates.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: June 10, 1997
    Assignee: Sandoz Ltd.
    Inventors: Jordi Berenguer Barra, Jose Rocas Sorolla
  • Patent number: 5493011
    Abstract: Water-insoluble azo colorants, their preparation and use The invention relates to monoazo and disazo compounds of the formula (I) ##STR1## in which D is the radical of a carbocyclic or heterocyclic diazo or bisdiazo component, R.sup.1 and R.sup.2, independently of one another, are each a substituted or unsubstituted aryl or heteroaryl radical, X.sup.1 and X.sup.2, independently of one another, are each ring-forming ether oxygen or a substituted or unsubstituted imide grouping and n has the value 0 or 1, in which rings A and B, independently of one another, can each be additionally substituted and/or carry substituted or unsubstituted fused rings.These new compounds of the formula (I) are obtained by coupling diazotized amines or diamines of the type D--NH.sub.2 or H.sub.2 N--D--NH.sub.2 with (benzoxazol-2-yl)- or (benzimidazol-2-yl)-arylacetamides.Depending on the presence and length of alkyl chains, the compounds of the formula (I) are suitable for use as pigments, disperse dyes or oil-soluble dyes.
    Type: Grant
    Filed: November 6, 1992
    Date of Patent: February 20, 1996
    Assignee: Hoechst AG
    Inventors: Rudiger Jung, Reinhold Deubel
  • Patent number: 5484900
    Abstract: 1:2 chromium complex dyestuffs of the formula (I) ##STR1## in which A, B, R.sup.1, R.sup.2, R.sup.3, R.sup.4, p, m, n, n' and Cat.sup.(+) have the meaning given in the description, are suitable for dyeing and printing amido-containing materials.
    Type: Grant
    Filed: February 25, 1994
    Date of Patent: January 16, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventor: Winfried Mennicke
  • Patent number: 5446135
    Abstract: Dyes having the specific structural formula (1) set out below, their copper salt dyes, water-soluble azo dyes containing the dyes or the copper salt dyes, and polarizing films containing the water-soluble azo dyes: ##STR1## wherein A means a benzene or naphthalene ring having a sulfone group or a base thereof, Y and Z individually denote a group of the following formula (a); ##STR2## wherein R.sup.2 is a hydrogen atom, a methyl group, a methoxyl group or an ethoxyl group and R.sup.3 is a methyl, methoxyl or ethoxyl group,R.sup.1 represents an amino, C.sub.1-4 alkylamino, C.sub.2-4 alkylcarboxyamino, benzoylamino or phenylamino group bonded to the 6 or 7 position of the naphthalene ring, and X denotes a hydrogen, sodium, potassium or lithium atom, with the proviso that Y and Z are different but, when both R.sup.2 s are hydrogen atoms and both R.sup.3 s are methoxyl groups, Y and Z may be the same.
    Type: Grant
    Filed: March 14, 1994
    Date of Patent: August 29, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Tsutami Misawa, Akira Ogiso, Rihoko Imai, Hisato Itoh
  • Patent number: 5298608
    Abstract: A metal chelate compound comprising a monoazo compound of the following formula (I): ##STR1## (wherein A is a residue forming a hetero ring together with the carbon atom and the nitrogen atom to which it is bonded, B is a residue forming an aromatic group together with the two carbon atoms to which it is bonded, and X is a hydrogen atom or a cation), and a metal, and an optical recording medium comprising a substrate and a recording layer formed thereon for information to be written in and/or read out by laser, wherein said recording layer contains the metal chelate compound comprising a monoazo compound of the above formula (I) and a metal.
    Type: Grant
    Filed: January 16, 1992
    Date of Patent: March 29, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Tetsuo Murayama, Shuichi Maeda, Chiyoko Fukabori, Takumi Nagao
  • Patent number: 5270455
    Abstract: A metal complex suitable as dyes for the dyeing of a wide range of textile and non-textile materials, particularly leather and fur, said metal complex of a compound of the formula ##STR1## in which D and D.sub.1, independently of one another, are each the radical of a diazo component of the benzene or naphthalene series and M is a phenylene radical which may be further substituted.
    Type: Grant
    Filed: July 27, 1992
    Date of Patent: December 14, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Ulrich Schlesinger
  • Patent number: 5250671
    Abstract: The novel unsymmetrical 1:2 chromium complex dyestuffs of the formula ##STR1## in which the substituents R.sup.1, R.sup.2, R.sup.3, n and Cat.sup.(+) have the meaning given in the description, are highly suitable for the dyeing and printing of natural and synthetic amido-containing materials in predominantly red hues having good light, wet and diffusion fastness properties.
    Type: Grant
    Filed: September 8, 1992
    Date of Patent: October 5, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventor: Winfried Mennicke
  • Patent number: 5243031
    Abstract: A process for the production of a monoazo lake coated with a water-insoluble metal salt of rosin, which comprises the steps of:(a) adjusting a mixed solution containing a monoazo dye having a water-soluble group and an alkali metal or ammonium salt of rosin to pH of 8 to 12, and adding an stoichiometeric amount of a metal salt of at least one metal for insolubilizing rosin selected from the group consisting of zinc, aluminum, copper and manganese to form a water-insoluble rosin metal salt, and(b) adjusting the resultant mixture containing the water-insoluble rosin metal salt to pH of 9 to 12 and adding a metal salt of at least one metal for forming a lake of a monoazo dye selected from the group consisting of calcium, barium and strontium to form a monoazo lake.
    Type: Grant
    Filed: January 6, 1992
    Date of Patent: September 7, 1993
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Hitoshi Sugamo, Nobuyuki Tomiya, Yusuke Watabe
  • Patent number: 5233027
    Abstract: The new disazo dyestuffs of the formula (I) ##STR1## in which the substituents and indices have the meaning given in the description, and salts thereof are outstandingly suitable for dyeing cellulose-containing materials and leather in blue shades having good wet- and light-fastnesses.
    Type: Grant
    Filed: May 23, 1991
    Date of Patent: August 3, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rolf Hinrichs, Klaus Kunde
  • Patent number: 5229502
    Abstract: A process is described for the preparation of pure, asymmetric 1:2 chromium complex dyes containing at least two groups which impart solubility in water, which process comprises reacting a mixture of two dyes of the formulaeF.sub.1 --(SO.sub.3 H).sub.t (1)andF.sub.2 --SO.sub.2 --Y (2)in which the symbols are as defined in claim 1 with a chromium donor in a molar ratio of 0.85:1.0 to 1.2:1.0 in a one-pot process under pressure at a temperature above 100.degree. C. and at a pH between 0 and 2 and then continuing the reaction at a slightly acid, neutral or slightly alkaline pH. The dyes obtained by the process according to the invention are suitable for dyeing, in particular, wool, silk, leather and synthetic polyamide fibres.
    Type: Grant
    Filed: February 21, 1990
    Date of Patent: July 20, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Gerhard Back, Alois Puntener
  • Patent number: 5204453
    Abstract: The invention relates to a process for the preparation of 1:2 chromium, 1:2 cobalt, 1:2 nickel or 1:2 iron complex azo dyes diazotisation, coupling and metallizing, without isolation of the coupling product, which process comprises diazotizing at least one amine of the benzene or naphthalene series in aqueous solution and coupling the diazonium compound so obtained to at least one coupling component of the benzene or naphthalene series or of the heterocyclic series, such that the azo dye obtained as intermediate contains groups suitable for metal complex formation, and carrying out the diazotization or coupling in the presence of a chromium, cobalt, nickel or iron donor.The dyes obtained by the process of the invention are suitable for dyeing in particular wool or synthetic textile polyamide fibre materials as well as leather, and for use as wood mordant dyes.
    Type: Grant
    Filed: December 30, 1991
    Date of Patent: April 20, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Bernard Chambon, Horst H. Jager, Rudiger Oxenius, Alois Puntener
  • Patent number: 5196518
    Abstract: A process for the preparation of azo dyes of formula ##STR1## wherein K is the radical of a coupling component of the benzene or naphthalene series or of the heterocyclic series, and the hydroxy group is attached to K adjacent to the azo group, X is hydrogen or nitro and M is an alkali metal ion, which process comprises coupling a diazo component of formula ##STR2## in the presence of one or more buffer mixtures and in the absence or presence of an alkali metal chloride, to a coupling component of formula ##STR3## in which formulae (2) and (3) K and X are as defined for formula (1). The present invention makes it possible to prepare the azo dyes in high yields.
    Type: Grant
    Filed: August 28, 1991
    Date of Patent: March 23, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Horst Langfeld, Claudio Puebla, Gunter Sereinig
  • Patent number: 5126435
    Abstract: A process for the preparation of azo dyes of formula ##STR1## wherein K is the radical of a coupling component of the benzene or naphthalene series or of the heterocyclic series, and the hydroxy group is attached to K adjacent to the azo group, X is hydrogen or nitro and M is an alkali metal ion or an ammonium ion, which process comprises coupling a diazo component of formula ##STR2## in the presence of a zinc salt and in an inert gas atmosphere, to a coupling component of formula ##STR3## in which formula (2) and (3) above K and X are as defined for formula (1). The process makes it possible to obtain the azo dyes in high yield.
    Type: Grant
    Filed: October 11, 1990
    Date of Patent: June 30, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans P. Joswig, Werner Huber
  • Patent number: 5047517
    Abstract: The invention relates to a yellow monoazo pigment which is obtained by diazotization of 2-amino-4-chloro-5-methylbenzene-1-sulfonic acid, coupling of the diazonium compound with 1-(3'-sulfophenyl)-3-methyl-5-pyrazolone and subsequent laking of the coupling product to the calcium salt.The new pigment has excellent heat stability and bleeding fastness and good light stability. It is particularly suitable for the pigmenting of polymeric plastics in the mass.
    Type: Grant
    Filed: September 28, 1989
    Date of Patent: September 10, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Walter Deucker
  • Patent number: 5037964
    Abstract: (i) Metal-free compounds of the formula ##STR1## These compounds are useful as dyes for paper and textiles.
    Type: Grant
    Filed: October 17, 1986
    Date of Patent: August 6, 1991
    Assignee: Sandoz Ltd.
    Inventors: Helmut A. Moser, Roland Wald
  • Patent number: 5026830
    Abstract: Process for the preparation of azo dyes of the formula ##STR1## in which K is the radical of a coupling component of the benzene or naphthalene series or of the heterocyclic series in which the hydroxyl group is attached to K in a position adjacent to the azo group, X is hydrogen or nitro and M is an alkali metal ion or ammonium ion, which comprises coupling a diazo component of the formula ##STR2## in the presence of an alkali metal chloride and ammonium chloride with a coupling component of the formula (3) ##STR3## K and X in the formulae (2) and (3) being as defined under formula (1). The present invention allows the preparation of the said azodyes in high yields.
    Type: Grant
    Filed: August 29, 1988
    Date of Patent: June 25, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Horst Langfeld, Claudio Puebla, Gunter Sereinig
  • Patent number: 5008379
    Abstract: Water-soluble, anionic, chromium complexes of disazo compounds, at least one of the complex-forming disazo compounds being of the formula, ##STR1## in which ##STR2## is the radical of a carboxy group-containing diazo component of the benzene or naphthalene series, the carboxy group being ortho to the azo group and the diazo component being free from other metallizable groups, andB-- is the radical of a diazo component of the benzene or naphthalene series free from metallizable substituents,which complexes contain at least one water-solubilizing group, are in free acid or salt form and are useful for dyeing and printing substrates such as natural and synthetic polyamides, polyurethanes and anodized aluminum, particularly fur-lined leather.
    Type: Grant
    Filed: October 29, 1987
    Date of Patent: April 16, 1991
    Assignee: Sandoz Ltd.
    Inventor: Herbert Holliger
  • Patent number: 5003051
    Abstract: A process for the preparation of azo dyes of the formula ##STR1## in which X is --NH.sub.2 or --OH, A is a benzene or naphthalene radical which can be substituted by nitro, halogen, sulfo, C.sub.2 -C.sub.6 alkanoylamino, C.sub.1 -C.sub.6 -alkoxycarbonylamino, sulfonamido and sulfone groups and B is a benzene radical which is monosubstituted or disubstituted by C.sub.1 -C.sub.6 alkyl, or a naphthalene radical which can be substituted by amino, phenylamino, C.sub.1 -C.sub.6 alkylamino and sulfo, or a 1-phenyl-3-methyl-5-pyrazlone radical which can be substituted by halogen, C.sub.1 -C.sub.6 alkyl and C.sub.1 -C.sub.6 alkoy, these radicals being bound to the azo group in the o-position with respect to the hydroxyl or amino groups, comprises diazotizing in aqueous solution an amine of the formula ##STR2## in the presence of at least one ketone of the formula ##STR3## in which R.sub.1 and R.sub.2, independently of one another, are each C.sub.1 -C.sub.
    Type: Grant
    Filed: August 23, 1989
    Date of Patent: March 26, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Ulrich Schlesinger, Peter Loew, Alois Puntener
  • Patent number: 5001226
    Abstract: Compounds of the formula ##STR1## 1:1 and 1:2 metal complexes thereof, salts of such compounds and metal complexes and mixture thereof, whereineach of B.sub.1 and B.sub.2 is independently hydroxy or amino,each D is independently ##STR2## wherein R is hydrogen, C.sub.1-4 alkyl, C.sub.5-6 cycloalkyl, phenyl, benzyl or phenylethyl,R.sub.1 is hydrogen, cyano, --COOR.sub.4, --CONR.sub.5 R.sub.6, --SO.sub.2 NR.sub.5 R.sub.6, ##STR3## wherein each R.sub.3 is independently hydrogen, C.sub.1-4 alkyl, --NR.sub.5 R.sub.6 or --CONR.sub.5 R.sub.6,R.sub.4 is C.sub.1-6 alkyl or phenyl(C.sub.1-3 alkyl),R.sub.7 is C.sub.1-4 alkyl,R.sub.8 is hydrogen or C.sub.1-4 alkyl, andR.sub.9 is --S--, --O-- or --NR.sub.5 --,R.sub.2 is hydrogen, hydroxy or C.sub.1-4 alkoxy,R.sub.2a is hydrogen, C.sub.1-4 alkyl or halo,M is hydrogen; C.sub.1-8 alkyl; (C.sub.1-4 alkoxy)C.sub.1-4 alkyl; C.sub.2-4 hydroxyalkyl; C.sub.5-6 cycloalkyl; C.sub.5-6 cycloalkyl substituted by 1 to 3 C.sub.1-4 alkyls; phenyl(C.sub.1-3 alkyl); phenyl (C.sub.
    Type: Grant
    Filed: December 19, 1989
    Date of Patent: March 19, 1991
    Assignee: Sandoz Ltd.
    Inventors: Helmut A. Moser, Roland Wald
  • Patent number: 4997917
    Abstract: The invention relates to a process for the preparation of asymmetrical 1:2 chromium complex dyes of not less than 90% purity and containing at least one water-solubilizing group, which process comprises reacting a mixture of two metallizable azo dyes that contain different diazo components and different coupling components, or a mixture of a metallizable azo dye and a metallizable azomethine dye, in the molar ratio of 0.85:1.0 to 1.2:1.0, with the proviso that only one of said two mixture components contains at least one water-solubilizing group, with a chromium donor, under pressure and at a temperature above 100.degree. C. and in the pH range from 0 to 2, and subsequently carrying out further reaction in a weakly acid, neutral or weakly alkaline pH range, utilizing a single vessel for all steps.The dyes obtained by the process of the invention are particularly suitable for dyeing wool or polyamide materials.
    Type: Grant
    Filed: March 4, 1985
    Date of Patent: March 5, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Walter Iff, Daniel Parisot, Hans Schaller
  • Patent number: 4996302
    Abstract: A process for the preparation of polyazo dyes is described which comprises(a) diazotizing a compound of the formula ##STR1## and coupling the product onto a compound of the formula ##STR2## (b) diazotizing a compound of the formula ##STR3## and coupling the product onto the product obtained according to (a); (c) diazotizing a compound of the formula ##STR4## and coupling the product onto the product obtained according to (b); (d) if desired, coupling of a further diazotized compound of the formula (3) onto the product obtained according to (c); and(e) if desired, metallizing the product obtained according to (c) or (d); and in which the symbols are as defined in claim 1. The polyazo dyes obtainable by the process are suitable for dyeing a wide range of textile and non-textile materials and, in particular, for dyeing leather.
    Type: Grant
    Filed: December 7, 1988
    Date of Patent: February 26, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Horst Langfeld
  • Patent number: 4996303
    Abstract: The invention relates to a process for the preparation of 1:2 metal complex azo dyes of formula ##STR1## wherein each X is hydrogen, halogen or nitro, K and K' are each independently of the other the radical of a coupling component of the benzene, naphthalene or pyrazolone series, Y and Y' are each --O-- or --N(R), wherein R is hydrogen, C.sub.1 -C.sub.4 alkyl or phenyl, Me is chromium or cobalt and Ka is a cation, and Y and Y' are attached to K and K' adjacent to the azo group, by coupling and metallising, which process comprises coupling, in aqueous solution, a diazo component of formula ##STR2## wherein X is as defined for formula (1), in the presence of the 5- to 30-fold molar amount of sodium and/or potassium chloride, based on the molar amount of diazo component, and in the presence of a compound that donates a chromium or cobalt atom, to coupling components of formulaeHK--YH and HK'--Y'H (3),wherein K, K', Y and Y' are as defined for formula (1).
    Type: Grant
    Filed: November 22, 1988
    Date of Patent: February 26, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Alois Puntener, Daniel Parisot
  • Patent number: 4994561
    Abstract: A process for the preparation of an azo dye of formula ##STR1## wherein K is the .beta.-naphthol radical, X is hydrogen or nitro and M is an alkali metal ion or an ammonium ion, which process comprises coupling an aqueous solution containing 15 to 30 percent by weight of a diazo component of formula ##STR2## and 6 to 20 mol % of an ammonium salt, based on the molar amount of the diazo component, at a pH in the range from 10.5 to 11.5 and in an inert gas atmosphere, to a coupling component of formula ##STR3## in which formulae (2) and (3) above K and X are as defined for formula (1).The present invention makes it possible to obtain the claimed azo dyes in high yield.
    Type: Grant
    Filed: June 8, 1990
    Date of Patent: February 19, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans P. Joswig, Werner Huber
  • Patent number: 4990598
    Abstract: The invention relates to chromium complexes of the formula ##STR1## in which A is the radical of a dicyclically metallizable azo or azomethine dye, B is the radical of a monoanionic bidentate complexible organic compound which is bonded to the chromium atom via oxygen atoms, L is a colorless monofunctional ligand, X is halogen-substituted C.sub.1-4 -alkanoyl, C.sub.1-4 -alkenoyl, halogen-substituted C.sub.1-4 -alkenoyl, monohalogenopyrimidinyl, dihalogenopyrimidinyl or trihalogenopyrimidinyl which is bonded to A and/or B via ##STR2## and R.sub.5 is hydrogen or C.sub.1-4 -alkyl, Ka is a cation, m is 1, 2 or 3, n is 1 or 2 and the SO.sub.3.sup..crclbar. Ka group is bonded to A and/or B. These chromium complexes are suitable for dyeing nitrogen-containing or hydroxy-containing materials and they produce level dyeings having good all-round fastness properties.
    Type: Grant
    Filed: November 7, 1984
    Date of Patent: February 5, 1991
    Inventors: Hans U. Schutz, Ulrich Schlesinger, Gerhard Back
  • Patent number: 4988805
    Abstract: The dyestuffs of the general formulae ##STR1## and salts thereof whereinX denotes hydrogen, alkoxy or NHR.sub.3,R denotes hydrogen, alkyl or alkoxy,R.sub.1 denotes alkyl,R.sub.2 and R.sub.3 denote hydrogen, alkyl, alkylcarbonyl, alkylsulphonyl, aryl, arylcar=bonyl, arylsulphonyl, aralkyl, aralkylcarbonyl or aminocarbonyl andm and n denote 1 or 2, andwherein the substituents mentioned can, in turn, be substituted by nonionic radicals or carboxylic or sulphonic acid groups customary in dyestuffs chemistry, are used for dyeing cellulose-containing materials and leather.
    Type: Grant
    Filed: July 14, 1988
    Date of Patent: January 29, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus Kunde