Sulfonic Acid Group Containing (-(o=)s(=o)-oh, Wherein H Of -oh May Be Replaced By The Ammonium Ion Or A Metal) Patents (Class 534/724)
  • Patent number: 7083674
    Abstract: A pigment dispersant represented by the following general formula (1) is provided: wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 each independently is —H, —Cl, —CH3, —CF3, —NO2, —COOCH(CH3)2 or —COOCH2CH2Cl; R11, R12, R13 and R14 each independently is —H, —Cl, —CH3 or —CN; M is one equivalent of a bivalent or trivalent metal; and n is an integer of 1 to 3.
    Type: Grant
    Filed: September 6, 2005
    Date of Patent: August 1, 2006
    Assignee: Toyo Ink Mfg. Co., Ltd.
    Inventors: Takashi Kamikubo, Tetsuya Sai
  • 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: 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: 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
  • Publication number: 20040198964
    Abstract: The invention relates to novel monoazo compounds of formula (1), wherein R1 represents 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═SO3−, 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 lightfastness.
    Type: Application
    Filed: February 13, 2004
    Publication date: October 7, 2004
    Inventors: Hans Joachim Metz, Uday T. Nabar, Frank Morgenroth, Chandrashekhar D Patil, Sunil D. Deval
  • Patent number: 6521032
    Abstract: Inks comprising a dye of formula (1) wherein X is hydroxy, unsubstituted or hydroxy-substituted C1-C4alkyl, vinyl or a radical —CH2—CH2—Z, wherein Z is a group removable under alkaline conditions or is C1-C24alkoxy unsubstituted or substituted in the alkyl moiety, which may further be interrupted in the alkyl moiety by oxygen; phenoxy unsubstituted or substituted in the phenyl ring; C1-C4alkylthio unsubstituted or substituted in the alkyl moiety; phenylthio unsubstituted or substituted in the phenyl ring; amino; N-mono- or N,N-di-C1-C24alkylamino unsubstituted or substituted in the alkyl moiety, which may further be interrupted in the alkyl moiety by oxygen or by a radical —NR1— in which R1 is hydrogen or unsubstituted or further substituted C1-C4alkyl; C10-C20terpeneamino; C5-C7cycloalkylamino unsubstituted or substituted in the cycloalkyl ring; phenyl- or naphthyl-amino or N—C1-C4alkyl-N-phenyl- or N—C1-C4alkyl-N-naphthyl-amino unsubstituted or su
    Type: Grant
    Filed: September 25, 2000
    Date of Patent: February 18, 2003
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Urs Lehmann, Marcel Frick
  • 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
  • Publication number: 20020139281
    Abstract: Reactive Red 23 magenta dye that is hydrolyzed to produce a passivated form having improved lightfastness in inkjet ink.
    Type: Application
    Filed: January 26, 2001
    Publication date: October 3, 2002
    Inventors: John L. Stoffel, Peter C. Morris
  • Patent number: 6458195
    Abstract: Reactive Red 23 magenta dye that is hydrolyzed to produce a passivated form having improved lightfastness in inkjet ink.
    Type: Grant
    Filed: January 26, 2001
    Date of Patent: October 1, 2002
    Assignee: Hewlett-Packard Company
    Inventors: John L Stoffel, Peter C. Morris
  • Publication number: 20020091241
    Abstract: This invention provides azo-metal complex dyes for a high-density optical disc recording medium having the following formula (I): 1
    Type: Application
    Filed: May 16, 2001
    Publication date: July 11, 2002
    Applicant: Industrial Technology Research Institute
    Inventors: Shin-Shin Wang, Hui-Ping Tsai, Wen-Yih Liao, Chien-Liang Huang, Tzuan-Ren Jeng
  • Patent number: 6379442
    Abstract: A composition comprising: (a) a water-soluble magenta dye; and (b) a dye of the Formula (1) or a salt thereof: wherein R1, R2, R3 are defined in the description.
    Type: Grant
    Filed: April 6, 2000
    Date of Patent: April 30, 2002
    Assignee: Avecia Limited
    Inventors: Aidan Joseph Lavery, Bachaspati Roy, Janette Watkinson, Mark Kenworthy
  • Patent number: 6210448
    Abstract: 1:2 chromium complex dyes of the formula: in which R signifies C1-9-alkyl or a radical of the formula: R1 signifies C1-4-alkyl, R2 signifies hydrogen or —SO3M, R3 signifies hydrogen, methyl or methoxy, R4 signifies hydrogen, methyl, methoxy or chloro, n signifies from 0 to 3, M signifies hydrogen or a non-chromophoric cation and Kat+signifies hydrogen or a non-chromophoric cation, are suitable for dyeing artificially produced oxide layers on aluminium or aluminium alloys and so give rise to highly lightfast dyeings in yellow shades.
    Type: Grant
    Filed: November 24, 1999
    Date of Patent: April 3, 2001
    Assignee: Clariant Finance (BVI) Limited
    Inventor: Klaus Körte
  • Patent number: 5376151
    Abstract: Disclosed is an original approach to solving the environmental problem associated with the use of Cr-based metallized azo dyes to deliver black shades on natural and synthetic substrates. This invention affords methods for both the synthesis of metallized dyes and the generation of black dyeings using those dyes without employing metals designated as priority pollutants at any stage in either method. The key element of the disclosure is the use of black 1:2 Fe complexes of azo dyes in lieu of currently used Cr-based complexes which are based on environmentally unfriendly priority pollutant metals without compromising the desirable high fastness properties of the latter complexes, an accomplishment heretofore assumed unachievable.
    Type: Grant
    Filed: April 16, 1993
    Date of Patent: December 27, 1994
    Assignee: North Carolina State University
    Inventors: Harold S. Freeman, Abraham Reife, Jolanta Sokolawska-Gajda
  • Patent number: 5256194
    Abstract: A recording liquid containing a dye, glycerine, an aliphatic monohydric alcohol and water. The dye is a mixture of C.I. Food Black 2 and at least one compound selected from compounds which are represented by the following general formulas [I] and [II]: ##STR1## [where Q1 is a phenyl group or a naphthyl group which are substituted by a lower alkyl carbonylamino group and a lower alkoxy group or a naphthyl group substituted by a SO.sub.3 M group, Q2 is a naphthyl group substituted by a SO.sub.3 M group or a phenyl group substituted by a lower alkoxy group, Q3 is a phenyl group, a naphthyl group, or a phenyl group or a naphthyl group which are substituted by a SO.sub.3 M group, R.sub.1 and R.sub.2 are each a lower alkyl group, a lower alkoxy group or a lower alkyl carbonylamino group, R.sub.3 is a hydrogen or a phenyl group substituted by a SO.sub.3 M group, n is 0 or 1, and M is an alkaline metal or an ammonium cation.
    Type: Grant
    Filed: September 2, 1992
    Date of Patent: October 26, 1993
    Assignee: Canon Kabushiki Kaisha
    Inventors: Osamu Nishiwaki, Kazuo Iwata, Shinichi Tochihara, Hitoshi Sugimoto
  • Patent number: 5125969
    Abstract: A recording liquid containing a dye, glycerine, an aliphatic monohydric alcohol and water. The dye is a mixture of C.I. Food Black 2 and at least one compound selected from compounds which are represented by the following general formulas [I] and [II]: ##STR1## where Q1 is a phenyl group or a naphthyl group which are substituted by a lower alkyl carbonylamino group and a lower alkoxy group or a naphthyl group substituted by a SO.sub.3 M group, Q2 is a naphthyl group substituted by a SO.sub.3 M group or a phenyl group substituted by a lower alkoxy group, Q3 is a phenyl group, a naphthyl group, or a phenyl group or a naphthyl group which are substituted by a SO.sub.3 M group, R.sub.1 and R.sub.2 are each a lower alkyl group, a lower alkoxy group or a lower alkyl carbonylamino group, R.sub.3 is a hydrogen or a phenyl group substituted by a SO.sub.3 M group, n is 0 or 1, and M is an alkaline metal or an ammonium cation.
    Type: Grant
    Filed: January 17, 1990
    Date of Patent: June 30, 1992
    Assignee: Canon Kabushiki Kaisha
    Inventors: Osamu Nishiwaki, Kazuo Iwata, Shinichi Tochihara, Hitoshi Sugimoto
  • 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: 4994111
    Abstract: The dye of the formula: ##STR1## which is suitable for use in aqueous inks, especially for ink jet printing.
    Type: Grant
    Filed: November 30, 1989
    Date of Patent: February 19, 1991
    Assignee: Canon Kabushiki Kaisha
    Inventors: Arthur Quayle, Cecil V. Stead
  • Patent number: 4931550
    Abstract: The dye of the formula: ##STR1## which is suitable for use in aqueous inks, especially for ink jet printing.
    Type: Grant
    Filed: May 5, 1987
    Date of Patent: June 5, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventors: Arthur Quayle, Cecil V. Stead
  • Patent number: 4904767
    Abstract: Asymmetric 1:2-chrome complex dyes of the formula: ##STR1## wherein A is the radical of 1-hydroxynaphthalene or 2-hydroxynaphthalene,R.sub.1 is hydrogen, chlorine or methyl,R.sub.2 is hydrogen, nitro or chlorine, andKa.sup.+ is a cation, and of the substituents X.sub.1, X.sub.2 and X.sub.3 one is an SO.sub.3 group, and the other two are hydrogen, X.sub.3 being hydrogen when R.sub.1 is chlorine and R.sub.2 is hydrogen,give blue shades on leather and other polyamides, which shades are lightfast and fast to wet processing.
    Type: Grant
    Filed: June 29, 1987
    Date of Patent: February 27, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Fabio Beffa, Alois Puntener, Peter Loew
  • Patent number: 4820309
    Abstract: Complexes of the formula ##STR1## wherein each R.sub.1 is independently (a) the radical of a coupling component of the active methylene non-cyclic or homocyclic series, (b) the radical of a coupling component of the heterocyclic series or (c) the radical of a coupling component of the monocyclic benzene series,with the proviso that at least one R.sub.1 is the radical of a coupling component of the active methylene non-cyclic or homocyclic series,each R.sub.2 is independently hydrogen, C.sub.1-4 alkyl or --SO.sub.2 NR.sub.4 R.sub.5,each R.sub.3 is independently hydrogen, halo, C.sub.1-4 alkyl or --SO.sub.2 NR.sub.4 R.sub.5, andeach M and M.sub.1 is independently hydrogen or a cation,wherein each R.sub.4 is independently hydrogen, C.sub.1-4 alkyl or C.sub.2-3 hydroxyalkyl, andeach R.sub.5 is independently hydrogen, C.sub.1-4 alkyl, C.sub.2-3 hydroxyalkyl, cyclohexyl, cyclohexyl substituted by methyl, phenyl or phenyl substituted by methyl, with the proviso that at least one of Ring A and R.sub.
    Type: Grant
    Filed: March 3, 1988
    Date of Patent: April 11, 1989
    Assignee: Sandoz Ltd.
    Inventor: Herbert Holliger
  • Patent number: 4668774
    Abstract: Novel dye salts of anionic dyes of the general formula I ##STR1## where F is a radical of an anionic dye, n is 1, 2, 3 or 4, and B.sup.1 and B.sup.2 independently of one another are each unsubstituted or substituted branched alkyl or alkyl-substituted cycloalkyl having a total of 10 to 36 carbon atoms, are very useful for dyeing solvents, printing inks or polymeric film-forming materials.
    Type: Grant
    Filed: April 23, 1985
    Date of Patent: May 26, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Hermann Loeffler, Rainer Dyllick-Brenzinger
  • Patent number: 4663441
    Abstract: Compounds of the formula I ##STR1## where K.sup..sym. is a cation, R is methyl or is phenyl which is unsubstituted or substituted by chlorine, bromine, methyl, methoxy or ethoxy, R.sup.1 is hydrogen, chlorine, bromine or nitro, R.sup.2 is hydrogen, chlorine, bromine, nitro, sulfamyl or hydroxysulfonyl, X and Y are each --O-- or --COO--, Z is --O-- or --NH--, D is a radical of a diazo component of the aniline or naphthylamine series and K is a radical of a coupling component, are very useful for dyeing natural and synthetic polyamide textile fibers and leather.
    Type: Grant
    Filed: September 16, 1985
    Date of Patent: May 5, 1987
    Assignee: BASF Aktiengesellschaft
    Inventor: Klaus Grychtol
  • Patent number: 4661587
    Abstract: Disclosed are chrome complex dyes of the formula ##STR1## and of the formula ##STR2## wherein Z and Z' independently of one another are each nitrogen or --CH--;X and X' independently of one another are each oxygen, or a group of the formula --NR--, in which R is hydrogen or C.sub.1 -C.sub.4 -alkyl, provided X is oxygen when Z is --CH-- and provided X' is oxygen when Z' is --CH--;A and B independently of one another are each a diazo component of a benzene or naphthalene radical which carries the hydroxyl or carboxyl group in the o-position with respect to the azo group;C and D independently of one another are each a benzene or naphthalene radical which carries in the o-position with respect to the azo or azomethine group a hydroxyl or carboxyl group, or the radical of an aliphatic or cycloaliphatic aminocarboxylic acid, if n.sub.2 or n.sub.
    Type: Grant
    Filed: May 3, 1985
    Date of Patent: April 28, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Ulrich Schlesinger, Fabio Beffa
  • Patent number: 4650859
    Abstract: Chrome azo-azomethine dyes are disclosed which contain a benzthiazolylphenyl or stilbenyl radical bound via an aldehyde group to the aldehyde moiety of the azomethine dyes. The dyes are particularly useful for dyeing wool, polyamide and leather.
    Type: Grant
    Filed: December 31, 1984
    Date of Patent: March 17, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Fabio Beffa
  • Patent number: 4625018
    Abstract: Novel red azo pigment--fortified latex compositions for use in printing inks. The novel pigment compositions have superior burn-out resistance and color strength. The novel pigment compositions are made by coupling orthanilic acid derivatives (including optionally, disulfonated amine derivatives) with B-napthal precipitating the metal salts and mixing with fortified latex dispersions. The fortified latex dispersion comprises a dispersed polymer phase in a dissolved polymer phase. The dispersed polymer is preferably a high molecular weight copolymer while the soluble polymer is preferably a low molecular weight acrylic copolymer containing carboxyl group functionality. The novel pigment compositions have superior color strength.
    Type: Grant
    Filed: August 26, 1985
    Date of Patent: November 25, 1986
    Assignee: Inmont Corporation
    Inventor: Byron G. Hays
  • Patent number: 4560744
    Abstract: Compounds which in the form of the free acids correspond to the formula ##STR1## where A is a radical of a diazo component or of an amine,B is a radical of a coupling component or of an aldehyde,R.sup.1 is chlorine or bromine,R.sup.2 is methoxy or ethoxy,X is .dbd.N-- or .dbd.CH--,Y is --O-- or --COO-- andZ is --O-- or --NH--,are dyes which are very suitable for dyeing nylons and natural polyamides.
    Type: Grant
    Filed: March 6, 1981
    Date of Patent: December 24, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Baumann, Klaus Grychtol
  • Patent number: 4537955
    Abstract: An unsymmetrical 1:2 chromium complex of a monoazo dyestuff and a disazo dyestuff which is non-fiber reactive and is free of sulfonamido and amino groups and which, in the form of the free acid has the formula: ##STR1## wherein A' is the radical of a 1-hydroxy-2-aminobenzene which is monosubstituted or disubstituted by chlorine, nitro, or sulfo, B' is a naphth-2-ol, resorcinol, p-(C.sub.1 -C.sub.6 -alkyl)-phenol, 1-phenol-3-methylpyrazol-5-one or acetoacetanilide radical, and the phenol group in the last two mentioned compounds can be substituted by C.sub.1 -C.sub.4 -alkyl C.sub.1 -C.sub.4 -alkoxy, chlorine or sulfo, K' is an unsubstituted or sulfo-substituted naphth-1-ol or naphth-2-ol radical, phenol which is substituted in the p-positioned by C.sub.1 -C.sub.6 -alkyl, an unsubstituted or sulfo-substituted 2-naphthylanime, and 1-phenol-3-methylpyrazol-5-one or an acetoactanilide radical, and the phenol group in the last two mentioned compounds can be substituted by C.sub.1 -C.sub.
    Type: Grant
    Filed: March 1, 1983
    Date of Patent: August 27, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Grychtol, Hans Baumann