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)
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Patent number: 7083674Abstract: 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: GrantFiled: September 6, 2005Date of Patent: August 1, 2006Assignee: Toyo Ink Mfg. Co., Ltd.Inventors: Takashi Kamikubo, Tetsuya Sai
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Patent number: 6984724Abstract: 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: GrantFiled: July 27, 2002Date of Patent: January 10, 2006Assignee: Clariant GmbHInventors: Hans Joachim Metz, Uday T. Nabar, Frank Morgenroth, Chandrashekhar D. Patil, Sunil D. Deval
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Patent number: 6913641Abstract: The invention relates to novel monoazo compounds of formula (1), wherein R represents H or Cl, M2+ represents Ca2+ or SR2+ and Y1=H and Y2=SO3? or Y1=SO3? and Y2=H. The compounds of formula (1) are characterized by their high drying power and high light-fastness.Type: GrantFiled: April 27, 2002Date of Patent: July 5, 2005Assignee: Clariant GmbHInventors: Hans Joachim Metz, Uday T. Nabar, Frank Morgenroth, Chandrashekhar D. Patil, Sunil D. Deval
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Patent number: 6913640Abstract: Novel improved single-phase mixed crystals of monoazo dyes laked with alkaline earth metal cations and ammonium cations in a molar ratio of about 1:2 having a fine particle size and substantially better fastness properties than similar known products are excellently suitable as tinctorially strong pigments. Also claimed is a process for the preparation of a single-phase mixed crystal pigment of formula wherein E is Mg, Ca or Sr, by crystallisation from an inert hydrophilic liquid in the presence of solvated catiens E++, NR5R6R7R8+, x is a number from 0.33 to 0.62 and y is a number from 0.76 to 1.34, and the concentration of solvated catiens E++ at the beginning of the crystallisation is higher than the concentration of solvated cations NR5R8R7R8+.Type: GrantFiled: January 15, 2002Date of Patent: July 5, 2005Assignee: CIBA Specialty ChemicalsInventors: Philippe Bugnon, Carolin Sansonnens, Greig Chisholm
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Publication number: 20040198964Abstract: 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: ApplicationFiled: February 13, 2004Publication date: October 7, 2004Inventors: Hans Joachim Metz, Uday T. Nabar, Frank Morgenroth, Chandrashekhar D Patil, Sunil D. Deval
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Patent number: 6521032Abstract: 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 suType: GrantFiled: September 25, 2000Date of Patent: February 18, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: Urs Lehmann, Marcel Frick
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Patent number: 6469147Abstract: 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: GrantFiled: February 9, 2001Date of Patent: October 22, 2002Assignee: Clariant Finance (BVI) LimitedInventors: Uwe Nickel, Rüdiger Jung, Klaus Saitmacher, Leonhard Unverdorben
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Publication number: 20020139281Abstract: Reactive Red 23 magenta dye that is hydrolyzed to produce a passivated form having improved lightfastness in inkjet ink.Type: ApplicationFiled: January 26, 2001Publication date: October 3, 2002Inventors: John L. Stoffel, Peter C. Morris
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Patent number: 6458195Abstract: Reactive Red 23 magenta dye that is hydrolyzed to produce a passivated form having improved lightfastness in inkjet ink.Type: GrantFiled: January 26, 2001Date of Patent: October 1, 2002Assignee: Hewlett-Packard CompanyInventors: John L Stoffel, Peter C. Morris
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Publication number: 20020091241Abstract: This invention provides azo-metal complex dyes for a high-density optical disc recording medium having the following formula (I): 1Type: ApplicationFiled: May 16, 2001Publication date: July 11, 2002Applicant: Industrial Technology Research InstituteInventors: Shin-Shin Wang, Hui-Ping Tsai, Wen-Yih Liao, Chien-Liang Huang, Tzuan-Ren Jeng
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Patent number: 6379442Abstract: 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: GrantFiled: April 6, 2000Date of Patent: April 30, 2002Assignee: Avecia LimitedInventors: Aidan Joseph Lavery, Bachaspati Roy, Janette Watkinson, Mark Kenworthy
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Patent number: 6210448Abstract: 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: GrantFiled: November 24, 1999Date of Patent: April 3, 2001Assignee: Clariant Finance (BVI) LimitedInventor: Klaus Körte
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Patent number: 5376151Abstract: 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: GrantFiled: April 16, 1993Date of Patent: December 27, 1994Assignee: North Carolina State UniversityInventors: Harold S. Freeman, Abraham Reife, Jolanta Sokolawska-Gajda
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Patent number: 5256194Abstract: 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: GrantFiled: September 2, 1992Date of Patent: October 26, 1993Assignee: Canon Kabushiki KaishaInventors: Osamu Nishiwaki, Kazuo Iwata, Shinichi Tochihara, Hitoshi Sugimoto
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Patent number: 5125969Abstract: 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: GrantFiled: January 17, 1990Date of Patent: June 30, 1992Assignee: Canon Kabushiki KaishaInventors: Osamu Nishiwaki, Kazuo Iwata, Shinichi Tochihara, Hitoshi Sugimoto
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Patent number: 4996303Abstract: 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: GrantFiled: November 22, 1988Date of Patent: February 26, 1991Assignee: Ciba-Geigy CorporationInventors: Alois Puntener, Daniel Parisot
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Patent number: 4994111Abstract: The dye of the formula: ##STR1## which is suitable for use in aqueous inks, especially for ink jet printing.Type: GrantFiled: November 30, 1989Date of Patent: February 19, 1991Assignee: Canon Kabushiki KaishaInventors: Arthur Quayle, Cecil V. Stead
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Patent number: 4931550Abstract: The dye of the formula: ##STR1## which is suitable for use in aqueous inks, especially for ink jet printing.Type: GrantFiled: May 5, 1987Date of Patent: June 5, 1990Assignee: Imperial Chemical Industries PLCInventors: Arthur Quayle, Cecil V. Stead
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Patent number: 4904767Abstract: 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: GrantFiled: June 29, 1987Date of Patent: February 27, 1990Assignee: Ciba-Geigy CorporationInventors: Fabio Beffa, Alois Puntener, Peter Loew
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Patent number: 4820309Abstract: 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: GrantFiled: March 3, 1988Date of Patent: April 11, 1989Assignee: Sandoz Ltd.Inventor: Herbert Holliger
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Patent number: 4668774Abstract: 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: GrantFiled: April 23, 1985Date of Patent: May 26, 1987Assignee: BASF AktiengesellschaftInventors: Hermann Loeffler, Rainer Dyllick-Brenzinger
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Patent number: 4663441Abstract: 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: GrantFiled: September 16, 1985Date of Patent: May 5, 1987Assignee: BASF AktiengesellschaftInventor: Klaus Grychtol
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Patent number: 4661587Abstract: 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: GrantFiled: May 3, 1985Date of Patent: April 28, 1987Assignee: Ciba-Geigy CorporationInventors: Ulrich Schlesinger, Fabio Beffa
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Patent number: 4650859Abstract: 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: GrantFiled: December 31, 1984Date of Patent: March 17, 1987Assignee: Ciba-Geigy CorporationInventor: Fabio Beffa
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Patent number: 4625018Abstract: 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: GrantFiled: August 26, 1985Date of Patent: November 25, 1986Assignee: Inmont CorporationInventor: Byron G. Hays
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Patent number: 4560744Abstract: 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: GrantFiled: March 6, 1981Date of Patent: December 24, 1985Assignee: BASF AktiengesellschaftInventors: Hans Baumann, Klaus Grychtol
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Patent number: 4537955Abstract: 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: GrantFiled: March 1, 1983Date of Patent: August 27, 1985Assignee: BASF AktiengesellschaftInventors: Klaus Grychtol, Hans Baumann