Azo Bonded Directly To A Hetero Ring Or To A Polycyclo Ring System Having A Hetero Ring As One Of The Cyclos Patents (Class 534/606)
- Plural azo groups in the same azo moiety attached indirectly to each other by nonionic bonding (Class 534/608)
- Acyclic carbon bonded directly to the azo group (Class 534/609)
- Additional hetero ring or polycyclo ring system having a hetero ring as one of the cyclos bonded directly to the azo group (Class 534/610)
- The hetero ring is one of the cyclos in a polycyclo ring system (Class 534/611)
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Patent number: 8921564Abstract: The invention relates to basic bisazo compounds according to formula (I) wherein all substituents are defined as in Claim 1, their production, their use as dyestuffs as well as material dyed with these dyestuffs.Type: GrantFiled: July 25, 2007Date of Patent: December 30, 2014Assignee: Clariant Finance (BVI) Ltd.Inventors: Ludwig Hasemann, Friedrich Lehr, Martin Oberholzer, Heidrun Schene
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Patent number: 8211606Abstract: A coloring compound is provided which is excellent in coloring ability and transparency, has high solubility in organic solvents, and is superior in light resistance. A toner, a sheet for heat-sensitive transfer recording and an ink that use the coloring compound are also provided.Type: GrantFiled: July 25, 2008Date of Patent: July 3, 2012Assignee: Canon Kabushiki KaishaInventors: Yasuaki Murai, Masashi Hirose, Masayoshi Kato, Takayuki Toyoda, Takeshi Miyazaki
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Publication number: 20120123101Abstract: This application relates to thiophene azo dyes for use as hueing agents, laundry care compositions comprising such thiophene azo dyes, processes for making such thiophene azo dyes, and laundry care compositions and methods of using the same. The thiophene azo dyes contain a formally charged moiety and are generally comprised of at least two components: at least one chromophore component and at least one polymeric component. Suitable chromophore components generally fluoresce blue, red, violet, or purple color when exposed to ultraviolet light, or they may absorb light to reflect these same shades. These thiophene azo dyes are advantageous in providing a hueing effect, for example, a whitening effect to fabrics, while not building up over time and causing undesirable blue discoloration to the treated fabrics. The thiophene azo dyes are also generally stable to bleaching agents used in laundry care compositions.Type: ApplicationFiled: November 1, 2011Publication date: May 17, 2012Inventors: Eduardo Torres, Xiaoyong Michael Hong, Robert L. Mahaffey, JR., Dominick J. Valenti, Gregory S. Miracle
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Patent number: 7993446Abstract: This invention relates to a dispersant for an organic pigment comprising a compound represented by the below-described formula (1) or (2), and also to its use. According to the present invention, it is possible to provide a dispersant or the like, which can afford a coating formulation for a color filter. The coating formulation is prevented from an increase in viscosity and a reduction in storage stability even when the concentration of a pigment is high, and can fabricate the color filter with excellent transparency and color quality.Type: GrantFiled: January 30, 2008Date of Patent: August 9, 2011Assignee: Dainichiseika Color & Chemicals Mfg. Co., Ltd.Inventors: Hiroaki Saikatsu, Hiromitsu Yanagimoto, Naoto Kamata, Michiei Nakamura
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Patent number: 7658770Abstract: The present invention relates to agents for coloring keratin fibers which comprise at least one cationic azodye of the general formula (I).Type: GrantFiled: February 26, 2009Date of Patent: February 9, 2010Assignee: The Procter & Gamble CompanyInventors: Cécile Pasquier, Eric Tinguely, Markus Speckbacher, Annik Marguet, Hans-Jürgen Braun
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Patent number: 7371831Abstract: Compounds of formula (I) wherein all substituents have the meanings as defined in the Specification, their production and their use.Type: GrantFiled: February 11, 2002Date of Patent: May 13, 2008Assignee: Clariant Finance (BVI) LimitedInventors: Martin Oberholzer, Jürgen Geiwiz
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Patent number: 7109312Abstract: The present invention provides a family of dark quenchers, termed Black Hole Quenchers (“BHQs”), that are efficient quenchers of excited state energy but which are themselves substantially non-fluorescent. Also provided are methods of using the BHQs, probes incorporating the BHQs and methods of using the probes.Type: GrantFiled: July 29, 2005Date of Patent: September 19, 2006Assignee: Biosearch Technologies, Inc.Inventors: Ronald M. Cook, Matt Lyttle, Daren Dick
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Patent number: 6518407Abstract: A novel reactive dye compound is disclosed. It comprises (a) at least one chromophore moiety; (b) at least one nitrogen-containing heterocycle; (c) a linking group to link each chromophore moiety to each nitrogen-containing heterocycle; characterised in that at least one nitrogen-containing heterocycle is substituted with at least one thio-derivative and at least one quaternized nitrogen derivative.Type: GrantFiled: February 13, 2001Date of Patent: February 11, 2003Assignee: The Procter & Gamble CompanyInventors: Earl David Brock, David Malcolm Lewis, Taher Iqbal Yousaf
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Patent number: 6140478Abstract: Basic azo compounds of formula I are suitable for coloring or printing especially of paper and leather.Type: GrantFiled: July 19, 1996Date of Patent: October 31, 2000Assignee: Clariant Finance (BVI) LimitedInventors: Jurgen Geiwiz, Helmut Anton Moser, Reinhard Pedrazzi
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Patent number: 6130319Abstract: A flocculating dye reduces bleed between two inks when they are applied side by side. A first ink comprises the flocculating dye which flocculates the dispersant-pigment of the second ink.Type: GrantFiled: April 3, 1998Date of Patent: October 10, 2000Assignee: Lexmark International, Inc.Inventors: James F. Feeman, Jing X. Sun
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Patent number: 6048968Abstract: Cationic azo dyes of the formula I ##STR1## where the variables are as defined in the specification, amines as their intermediates, processes for preparing them, their use for dyeing and printing natural or synthtic substrates, and their mixtures are described.Type: GrantFiled: May 5, 1999Date of Patent: April 11, 2000Assignee: BASF AktiengesellschaftInventors: Karl-Heinz Etzbach, Torsten Freund, Rainer Tresch
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Patent number: 5969112Abstract: A flocculating dye reduces bleed between two inks when they are applied side by side. A first ink comprises the flocculating dye which flocculates the dispersant-pigment of the second ink.Type: GrantFiled: April 3, 1998Date of Patent: October 19, 1999Assignee: Lexmark International, Inc.Inventors: James F. Feeman, Jing X. Sun
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Patent number: 5925745Abstract: A fiber-reactive dye corresponding to formula (1) ##STR1## in which: Fb is the radical of an azo dye, of a heavy metal complex azo dye, of a formazan dye, of a triphenodioxazine dye or of a phthalocyanine dye;U.sup.(+) is a permanent quaternary ammonium group;A.sup.(-) is a colorless anion, andR.sup.x, R.sub.4, G, Q and n are as defined in the specification, with the proviso that the dye contains at least one group of the vinylsulfone series, such as a group of the formula --SO.sub.2 Y, wherein Y is as defined in the specification, these dyes being capable of dyeing hydroxy- and/or carboxamido-containing fibres, such as cellulosic fibre and wool.Type: GrantFiled: May 11, 1998Date of Patent: July 20, 1999Assignee: Dystar, L.P.Inventors: Thomas S. Phillips, Ralph Svenningsen, Ronald P. Pedemonte
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Patent number: 5919914Abstract: Clathrates of bis?6-hydroxy-4-methyl-5-(3-methyl-imidazolium-1-yl)-3-(phen-4-ylazo)pyrid in-2-one!ethylene with aromatics of the general formula I ##STR1## where R.sup.1 is C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.5 -hydroxyalkyl, C.sub.1 -C.sub.5 -alkoxy, C.sub.1 -C.sub.5 -hydroxyalkoxy, C.sub.1 -C.sub.10 -alkyl which is interrupted by 1, 2 or 3 non-neighboring oxygen atoms and is unsubstituted or substituted by hydroxyl, C.sub.1 -C.sub.10 -alkoxy which is interrupted by 1, 2 or 3 non-neighboring oxygen atoms and is unsubstituted or substituted by hydroxyl, or is C.sub.1 -C.sub.6 -alkanoyl, hydroxy, carboxyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, phenylcarbonyl or C.sub.1 -C.sub.6 -alkenyl andR.sup.2 is R.sup.1, hydrogen or phenoxy,a process for their preparation and their use for the preparation of formulations of the dye.Type: GrantFiled: March 17, 1998Date of Patent: July 6, 1999Assignee: BASF AktiengesellschaftInventors: Manfred Ruske, Peter Erk, Heidi Hengelsberg
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Patent number: 5587465Abstract: Dyestuffs of the formula ##STR1## wherein D represents the radical of a diazo component;R represents hydrogen, an optionally substituted alkyl radical, a cycloaliphatic hydrocarbon radical, an optionally substituted phenyl radical, or a hetaryl radical;represents H, Cl, Br, CH.sub.3, CH.sub.2 SO.sub.3 H, CH(CH.sub.3)--SO.sub.3 H, CONH.sub.2, CN, COCH.sub.3, SO.sub.3 H, ##STR2## Y represents hydrogen, hydroxyl, an optionally substituted alkyl radical, an optionally substituted phenyl or benzyl radical, or carboxyl; andZ represents a fiber-reactive radical of the formula ##STR3## are suitable for dyeing fiber materials containing OH and amide groups and produce dyeings and prints with good fastness properties.Type: GrantFiled: January 4, 1990Date of Patent: December 24, 1996Assignee: Bayer AktiengesellschaftInventors: Karl-Heinz Sch undeh utte, Karl J. Herd
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Patent number: 5545724Abstract: The invention relates to cationically bridged tetrakisazo compounds, corresponding to formula I, ##STR1## wherein the individual symbols are defined as in claim 1, as well as residues and liquid preparations thereof. The compounds and their preparations are used for dyeing and printing hydroxy-group-containing or nitrogen-containing organic substrates by a known method. Preferred substrates are textile materials which consist of or contain cellulose, especially cotton, or also bast fibres, leather and preferably paper or paper pulp products, especially wood-containing paper.Type: GrantFiled: October 10, 1995Date of Patent: August 13, 1996Assignee: Sandoz Ltd.Inventor: Helmut A. Moser
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Patent number: 5424404Abstract: Biscationic azo dyes useful for dyeing or printing polymeric material have the formula ##STR1## where R.sup.1 is hydrogen or unsubstituted or phenyl-substituted C.sub.1 -C.sub.5 -alkyl,R.sup.2 is hydrogen or C.sub.1 -C.sub.5 -alkyl,R.sup.3 and R.sup.4 are independently of each other hydrogen or methyl,D is the radical of a diazo component, unsubstituted or substituted phenylene or a radical of the formula ##STR2## where Z is a bridge member, Y is hydrogen, C.sub.1 -C.sub.18 -alkyl, C.sub.2 -C.sub.6 -alkylene, xylidene or phenylene,An.sup..crclbar.Type: GrantFiled: June 11, 1993Date of Patent: June 13, 1995Assignee: BASF AktiengesellschaftInventors: Manfred Ruske, Udo Mayer
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Patent number: 5386015Abstract: Compounds of the formula ##STR1## and salts thereof, and mixtures of such compounds and salts, wherein F.sub.c is ##STR2## wherein D.sub.1 is an unsubstituted or substituted phenyl or naphthyl diazo component radical,each of Q.sub.1, Q.sub.2 and Q.sub.3 is independently hydrogen or a substituent,each R.sub.5 is independently hydrogen, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,each R.sub.6 is independently hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, (C.sub.1-4 alkyl)carbonylamino or --NH--CO--NH.sub.2,R.sub.16 is hydrogen or --SO.sub.3 H,r is 1 or 2, andt is 2 or 3, andb is 1 or 2,whereineach R.sub.1 is independently hydrogen or C.sub.1-4 alkyl,each R.sub.7 is independently hydroxy, C.sub.1-4 alkoxy or --NH.sub.2,each Z is independently ##STR3## and each m is independently 0 or 1.Type: GrantFiled: July 9, 1993Date of Patent: January 31, 1995Assignee: Sandoz Ltd.Inventors: Paul Doswald, Werner Koch
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Patent number: 5359041Abstract: Dyestuffs of the formula ##STR1## in which the substituents have the meaning given in the description, are suitable for the dyeing and printing of, for example, cellulose and polyamides.Type: GrantFiled: July 1, 1992Date of Patent: October 25, 1994Assignee: Bayer AktiengesellschaftInventors: Wolfram Reddig, Karl-Joef Herd
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Patent number: 5352334Abstract: Metal-free compounds of the formula ##STR1## and 1:1 and 1:2 metal complexes thereof and acid addition salts of such metal-free compounds and 1:1 and 1:2 metal complexes,whereineach B is --A.sub.1 --NR.sub.7 R.sub.8 or --A.sub.1 --.sup..sym. NR.sub.7 R.sub.8 R.sub.9 A.sup..crclbar., the two B's being identical,whereineach A.sub.1 is linear or branched C.sub.2-8 alkylene,each R.sub.1 is hydrogen, C.sub.1-4 alkyl, C.sub.5-6 cycloalkyl, phenyl, benzyl or phenylethyl, the two R.sub.1 's being identical,each R.sub.2 is independently halo, hydroxy, nitro, carboxy, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,each T is hydrogen, cyano, --COOR.sub.4, --CON(R.sub.5).sub.2, --SO.sub.2 N(R.sub.5).sub.2,the two T's being identical, ##STR2## wherein each R.sub.3 is independently hydrogen, C.sub.1-4 alkyl, --N(R.sub.5).sub.2 or --CON(R.sub.5).sub.2,each R.sub.4 is C.sub.1-6 alkyl or phenyl(C.sub.1-3 alkyl),each R.sub.6 is C.sub.1-4 alkyl, andeach X.sub.a is --O--, --S-- or --NR.sub.5 --, andX.sub.Type: GrantFiled: November 25, 1992Date of Patent: October 4, 1994Assignee: Sandoz Ltd.Inventors: Helmut A. Moser, Roland Wald
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Patent number: 5342927Abstract: Reactive dyestuffs of the formula ##STR1## in which X is ##STR2## and Z is a heterocyclic reactive group and the remaining groups have the meaning given in the description, are highly suitable for the dyeing and printing of hydroxyl- or amido-containing materials.Type: GrantFiled: July 21, 1992Date of Patent: August 30, 1994Assignee: Bayer AktiengesellschaftInventors: Wolfram Reddig, Karl-Josef Herd
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Patent number: 5328995Abstract: The compounds of the formula ##STR1## where the substituents are as defined in claim 1, are direct dyes for various substrates, in particular cellulosic fibre materials. They are high temperature resistant and therefore are particularly highly suitable for the one-bath, single-stage dyeing of polyester/cotton blend fabrics with a disperse dye for the polyester fibres under the dyeing conditions for polyester fibres.Type: GrantFiled: January 27, 1993Date of Patent: July 12, 1994Assignee: Ciba-Geigy CorporationInventors: Rudolf Schaulin, Urs Lauk
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Patent number: 5306813Abstract: A compound which, in the free acid form, is of Formula (1): ##STR1## wherein: D is optionally substituted phenyl or optionally substituted naphthyl;K is optionally substituted phenylene or optionally substituted naphthylene;R.sup.1 and R.sup.4 are each independently H or optionally substituted alkyl;R.sup.2 and R.sup.3 are each independently H or optionally substituted alkyl, provided at least one of R.sup.2 and R.sup.3 is optionally substituted alkyl;B is H, optionally substituted alkyl or optionally substituted each A is H or a substituent; andeachA is H or a substituent; andL is an optionally substituted divalent organic radical. The compound is useful as a reactive dye for textiles.Type: GrantFiled: January 22, 1993Date of Patent: April 26, 1994Assignee: Imperial Chemical Industries PLCInventors: Andrew H. M. Renfrew, John A. Taylor
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Patent number: 5284939Abstract: There is described a process for the preparation of highly concentrated aqueous solutions of specific cationic azo dyes. The solutions are prepared by diazotising a diazo component in a solution which contains sulfuric acid, coupling the diazotised component to a coupling component, treating the resultant azo dye with a bicarbonate, and converting the dye bicarbonate with an organic acid into the dye salt of said acid.Type: GrantFiled: May 14, 1992Date of Patent: February 8, 1994Assignee: Ciba-Geigy CorporationInventors: Alex Nicopoulos, Hanspeter Birri, Gerhard Hanika
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Patent number: 5264560Abstract: Quaternized azo dyes whose diazo components are derived from a five-membered nitrogen-containing aromatic aminoheterocycle and whose coupling components are derived from the aniline series are prepared by reacting to corresponding neutral dye-bases with an alkylating agent in .gamma.-butyrolactone as inert diluent.Type: GrantFiled: July 17, 1992Date of Patent: November 23, 1993Assignee: BASF AktiengesellschaftInventors: Guenter Hansen, Johannes P. Dix, Helmut Reichelt, Clemens Grund
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Patent number: 5241054Abstract: The novel azo dyes of formula I as indicated in claim 1 are suitable for dyeing and printing, especially paper of all kinds.Type: GrantFiled: December 17, 1990Date of Patent: August 31, 1993Assignee: Ciba-Geigy CorporationInventor: Willy Stingelin
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Patent number: 5175260Abstract: Disazo dyes suitable for preparing inks have the formula ##STR1## where m is 1 or 2,n is 0 or 1,Z.sup.1 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl,Z.sup.2 is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkanoyl, substituted or unsubstituted benzoyl, C.sub.1 -C.sub.4 -alkylsulfonyl, substituted or unsubstituted phenylsulfonyl or a derivatized 1,3,5-triazinyl radical, andD is the radical of a diazo component of the class of the thiazole, thiophene, aminobenzoic acid or phenylenediamine compounds.Type: GrantFiled: August 8, 1991Date of Patent: December 29, 1992Assignee: BASF AktiengesellschaftInventors: Gunter-Rudolf Schroeder, Udo Mayer
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Patent number: 5175259Abstract: Reactive dyes of the formula ##STR1## where n is 1 or 2,X is a six-membered halogen-containing nitrogen heterocycle,L.sup.1, depending on n, is fluorine, chlorine, C.sub.1 -C.sub.4 -alkoxy, phenoxy, C.sub.1 -C.sub.4 -alkyl, substituted or unsubstituted phenyl or a bridge member which has one or two hydroxysulfonyl groups,D is the radical of a diazo component of the aniline or naphthalene series which has at least one hydroxysulfonyl group,L.sup.2 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.8 -alkyl,L.sup.3 is the cationic radical of an aromatic heterocycle which is linked to the pyridone ring via a nitrogen atom, andL.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl,with the proviso that the number of hydroxysulfonyl groups in the molecule exceeds that of the cationic groups by at least one, are useful for dyeing and printing hydroxyl- or nitrogen-containing substrates.Type: GrantFiled: February 28, 1992Date of Patent: December 29, 1992Assignee: BASF AktiengesellschaftInventors: Joerg L. Jessen, Manfred Ruske, Knut Kessel, Manfred Patsch
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Patent number: 5077396Abstract: Compounds of the formula ##STR1## wherein each A is independently linear or branched C.sub.2-6 alkylene or linear or branched C.sub.3-6 alkylene substituted by hydroxy,each D is independently the radical of a diazo component of the benzene, azobenzene or naphthalene series, E is a divalent radical attached to each --N.sup..sym. R.sub.3 R.sub.4 -- radical through an aliphatic carbon atom,each R.sub.1 is independently hydrogen, C.sub.1-4 alkyl, cyclohexyl, phenyl or phenyl(C.sub.1-2 alkyl),each R.sub.2 is independently hydrogen, cyano, --COOR.sub.5, --CONR.sub.6 R.sub.7 or ##STR2## wherein R.sub.5 is hydrogen, C.sub.1-4 alkyl or phenyl(C.sub.1-2 alkyl),each of R.sub.6 and R.sub.7 is independently hydrogen or C.sub.1-4 alkyl,each R.sub.8 is independently C.sub.1-4 alkyl, and r is 0, 1, 2 or 3,each R.sub.3 is independently C.sub.1-4 alkyl or C.sub.1-4 alkyl monosubstituted by halo, cyano, hydroxy or phenyl,each R.sub.4 is independently hydrogen, C.sub.1-4 alkyl or C.sub.Type: GrantFiled: May 14, 1990Date of Patent: December 31, 1991Assignee: Sandoz Ltd.Inventors: Helmut A. Moser, Roland Wald
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Patent number: 5059683Abstract: Compounds of the formula ##STR1## and acid addition salts thereof whereinA.sub.1 is C.sub.1-8 alkylene; C.sub.2-8 alkylene substituted by 1 or 2 substituents selected from hydroxy, halo and cyano; C.sub.2-8 alkenylene; cyclohexylene; cyclohexylene substituted by 1 to 3 C.sub.1-4 alkyl groups; phenylene or phenylene substituted by 1 or 2 substituents selected from halo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy,B.sub.1 is ##STR2## wherein the quaternized nitrogen atom is bound to a carbon atom of A.sub.1,R is hydrogen, C.sub.1-4 alkyl, C.sub.5-6 cycloalkyl, phenyl, benzyl or phenylethyl,T is hydrogen, cyano, --COOR.sub.1, --CON(R.sub.2).sub.2, --SO.sub.2 N(R.sub.2).sub.2, ##STR3## wherein R.sub.1 is C.sub.1-6 alkyl or phenyl(C.sub.1-3 alkyl),each R.sub.3 is independently hydrogen, C.sub.1-4 alkyl, --CON(R.sub.2).sub.2 or --N(R.sub.5).sub.2, andX.sub.1 is --S--, --O-- or --N(R.sub.5)--,Y is hydrogen or a chromophoric group, andZ is ##STR4## wherein R.sub.11 is ##STR5## wherein W is --NR.sub.6 R.sub.7 or --.sup..sym.Type: GrantFiled: May 5, 1989Date of Patent: October 22, 1991Assignee: Sandoz Ltd.Inventors: Helmut A. Moser, Roland Wald
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Patent number: 5037964Abstract: (i) Metal-free compounds of the formula ##STR1## These compounds are useful as dyes for paper and textiles.Type: GrantFiled: October 17, 1986Date of Patent: August 6, 1991Assignee: Sandoz Ltd.Inventors: Helmut A. Moser, Roland Wald
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Patent number: 5023324Abstract: Disazo and trisazo compounds free of sulfo groups which contain 6-hydroxy-4-methyl-3-N-pyridiniumpyridone-2 coupling component radicals, the preferred compounds being of the formula ##STR1## wherein R is a tetrazo component radical,each R.sub.1 is independently hydrogen, C.sub.1-4 alkyl, C.sub.2-4 hydroxyalkyl the hydroxy group of which is in other than the 1-position or --NR.sub.3 R.sub.4, wherein each of R.sub.3 and R.sub.4 is independently n-C.sub.1-4 alkyl,each R.sub.2 is independently hydrogen, n-C.sub.1-4 alkyl, n-C.sub.1-4 hydroxyalkyl or C.sub.1-4 alkoxy, andeach A.sup..crclbar. is an anion,and liquid and granulated dye compositions comprising such compounds, are useful for dyeing paper and basically dyeable substrates such as polymers and copolymers of acrylonitrile and dicyanoethylene and synthetic polyesters and polyamides modified to contain acid groups. Dyeings on paper are brilliant and possess good light fastness and good fastness to water and alcohol.Type: GrantFiled: July 29, 1986Date of Patent: June 11, 1991Assignee: Sandoz Ltd.Inventor: Helmut Moser
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Patent number: 5015292Abstract: A recording fluid for the ink jet process contains a water-miscible organic solvent and a dye of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each have specified meanings, An.crclbar. is an anion and X is a bridge member of the formula ##STR2## where Y and the rings A and B each have specified meanings.Type: GrantFiled: January 23, 1989Date of Patent: May 14, 1991Assignee: BASF AktiengesellschaftInventors: Horst Bruder, Rainer Dyllick-Brenzinger, Udo Mayer, Steven J. Bares
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Patent number: 5001229Abstract: Basic dyestuffs of the formula ##STR1## or tautomeric forms thereof, whereinR.sub.1 and R.sub.2 stand for hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen,Q - E stands for C-S, C-O, C-NH or N.sup..sym. -N.sup..crclbar.,A stands for C.sub.1 -C.sub.4 -alkylene,W stands for the radical of an aliphatic mono-, di-, tri-, tetra-, penta-, hexa- or heptamine, which can be protonated or quaternized,n stands for 0 to 1.5 andp stands for 1.3 to 10,are suitable for dyeing materials which can be dyed with basic dyestuffs.Type: GrantFiled: December 16, 1988Date of Patent: March 19, 1991Assignee: Bayer AktiengesellschaftInventors: Gunter Franke, Peter Wild
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Patent number: 5001226Abstract: 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: GrantFiled: December 19, 1989Date of Patent: March 19, 1991Assignee: Sandoz Ltd.Inventors: Helmut A. Moser, Roland Wald
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Patent number: 4968781Abstract: A reactive dye of the formula ##STR1## in which Fa is the radical of an organic dye of the monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide series, T is a negative substituent, one X is a detachable substituent and the other X is a group of the formula ##STR2## A is arylene, V is hydrogen, a substituted or unsubstituted C.sub.1 -C.sub.4 alkyl radical or a radical of the formula --(CH.sub.2).sub.q --SO.sub.2 --Z, Z is a --CH.dbd.CH.sub.2 or CH.sub.2 --Y radical and Y is an inorganic or organic radical which is detachable under alkaline conditions, q, m and n are independently of one another an integral number from 2 to 6, R and R' are independently of one another hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl, and r is 1 or 2.Type: GrantFiled: March 28, 1988Date of Patent: November 6, 1990Assignee: Ciba-Geigy CorporationInventors: Karl Seitz, Karl Hoegerle
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Patent number: 4921945Abstract: 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: GrantFiled: May 25, 1988Date of Patent: May 1, 1990Assignee: Ciba-Geigy CorporationInventor: Willy Stingelin
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Patent number: 4898933Abstract: Water-soluble azo compounds having useful fiber-reactive dye properties conforming to the general formula ##STR1## in which: A is phenylene which may be substituted by lower alkoxy, lower alkyl, chlorine, sulfo and carboxy, or is a radical of the formula ##STR2## in which W is a direct bond or a radical of the formula --CH.dbd.CH-- or --NH--CO--NH-- and R* denotes hydrogen, nitro, sulfo, carboxy, methyl, ethyl, methoxy or ethoxy;n is the number zero or 1;B is a radical of the formula ##STR3## where R is equal to carboxy or carbamoyl; M is hydrogen or an alkali metal;K is a radical of the formula ##STR4## in which D is phenylene which may be substituted by chlorine, bromine, lower alkyl, lower alkoxy, carboxy and sulfo, or unsubstituted or sulfo substituted naphthylene;R.sup.1 is hydrogen, chlorine, lower alkyl or lower alkoxy;R.sup.2 is hydrogen or lower alkyl;G is carboxy, methyl or lower carbalkoxy;Y is vinyl, .beta.-sulfatoethyl or .beta.-chloroethyl;m is the number zero or 1;Z is .alpha.- or .beta.Type: GrantFiled: May 5, 1989Date of Patent: February 6, 1990Assignee: Hoechst AktiengesellschaftInventors: Ludwig Schlafer, Hartmut Springer, Reinhard Hahnle
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Patent number: 4897469Abstract: Azo reactive dyes of the aniline series for dye or printing fiber materials of the formula ##STR1## wherein K is the radical of a coupling component, and Z is a vinyl sulfonyl reactive group ortho- or para- to the azo bridge.Type: GrantFiled: April 1, 1988Date of Patent: January 30, 1990Assignee: BASF AktiengesellschaftInventors: Heinz Eilingsfeld, Ruediger Iden
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Patent number: 4883866Abstract: Methine-azo compounds of the formula ##STR1## in which A is the complement to a heterocyclic 5- or 6-membered ring which has a quaternized N atom as a ring member, which can contain further hetero atoms and which can be substituted and/or fused with carbocyclic or heterocyclic rings,R is hydrogen, cyano or C.sub.2 -C.sub.3 -alkylene which is bonded to an N atom of ring A to form a 5- or 6-membered ring,B is substituted or unsubstituted phenylene or naphthylene,X.sup..crclbar.Type: GrantFiled: February 29, 1988Date of Patent: November 28, 1989Assignee: Ciba-Geigy CorporationInventor: Peter Mockli
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Patent number: 4880916Abstract: 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: GrantFiled: March 24, 1988Date of Patent: November 14, 1989Assignee: Ciba-Geigy CorporationInventor: Jean-Marie Adam
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Patent number: 4877412Abstract: Compounds of the formula ##STR1## in free acid or salt form and internal, external and acid addition salts thereof, whereinK is ##STR2## wherein R.sub.3 -R.sub.5, R.sub.20, R.sub.21 and X-Z are as defined in the specification,each of Q.sub.1 and Q.sub.2 is independently hydrogen or --SO.sub.3 M.sub.1,each R.sub.1 and R.sub.2 is independently hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or --COOM, andn is 0 or 1,wherein each M and M.sub.1 is independently hydrogen or a nonchromophoric cation, with the provisos that (i) the compound contains at least one --SO.sub.3 M or --SO.sub.3 M.sub.1 group, (ii) when K is a gruop of Formula (a), at least one of R.sub.4 and R.sub.5 is hydrogen, (iii) the total number of anionic groups equals or exceeds the total number of basic and cationic groups, (iv) the positive charge of each cationic group is balanced by the negative charge of an --SO.sub.3.sup..crclbar. or --COO.sup..crclbar.Type: GrantFiled: March 31, 1988Date of Patent: October 31, 1989Assignee: Sandoz Ltd.Inventor: Reinhard Pedrazzi
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Patent number: 4875903Abstract: Compounds of the formula ##STR1## wherein each R.sub.1 is independently hydrogen, C.sub.1-4 alkyl or C.sub.1-4 alkyl monosubstituted by hydroxy, halo, cyano or C.sub.1-4 alkoxy,each of X.sub.1 and X.sub.3 is independently halo, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenyl, phenoxy, amino or an aliphatic, cycloaliphatic, aromatic or heterocyclic amino group,each of X.sub.2 and X.sub.4 is independently an aliphatic, cycloaliphatic, aromatic or heterocyclic amino group containing at least one protonatable nitrogen atom or quaternary ammonium group,m is 0 or 1, andeach of n.sub.1 and n.sub.2 is independently 0 or 1, with the proviso that n.sub.1 +n.sub.2 is 1 or 2,wherein each halo is independently fluoro, chloro or bromo, with the provisos that (1) the total number of basic and cationic groups present as X.sub.1 -X.sub.Type: GrantFiled: June 5, 1987Date of Patent: October 24, 1989Assignee: Sandoz Ltd.Inventor: Reinhard Pedrazzi
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Patent number: 4865990Abstract: A colored compound containing a cationic group and a cellulose reactive group, especially a compound of the formula:A--Y--B IY'--B IIwhereinA is the cationic group;Y is a chromophore;Y' is a cationic chromophoreandB is the reactive group, which is suitable for the preparation of a protein adsorbent or precipitant for use in the separation of mixtures of proteins.Type: GrantFiled: July 9, 1987Date of Patent: September 12, 1989Assignee: Imperial Chemical Industries PlcInventors: Cecil V. Stead, Christopher R. Lowe
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Patent number: 4847364Abstract: Methine-azo compounds of the formula ##STR1## in which A is the complement to a heterocyclic 5- or 6-membered ring which has a quaternized N atom as a ring member, which can contain further hetero atoms and which can be substituted or/and be fused with carbocyclic or heterocyclic rings,R is hydrogen, cyano or C.sub.2 --C.sub.3 -alkylene which is bonded to an N atom of ring A to form a 5- or 6-membered ring,B is substituted or unsubstituted phenylene or naphthylene,X.sup..crclbar. is an anion andKK is the radical of an open-chain coupling component which contains active methylene groups, except that, if A is the complement to a pyridinium ring, KK cannot be the radical of acetoacetanilide which is unsubstituted or alkyl-substituted in the aniline ring.They are suitable for use as dyes for dyeing and printing cationically dyeable substrates, in particular paper.Type: GrantFiled: June 16, 1987Date of Patent: July 11, 1989Inventor: Peter Mockli
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Patent number: 4820806Abstract: Metal-free monoazo and disazo compounds of the formulaCH.sub.2 .dbd.CH--SO.sub.2 --W.sub.1 --D--N.dbd.N--K--(W.sub.2 --Z).sub.n,1:1 and 1:2 metal complexes of such metallizable metal-free compounds and acid addition salts of such metal-free compounds and 1:1 and 1:2 metal complexes, whereinD is the radical of a diazo component of the benzene, naphthalene or tetrahydronaphthalene series,K is the radical of a coupling component of the benzene, naphthalene, pyrazol-5-one, pyridine, pyridone, barbituric acid, quinoline, isoquinoline, benzeneazobenzene, benzeneazonaphthalene, naphthaleneazobenzene, naphthaleneazonaphthalene, tetrahydronaphthaleneazobenzene, tetrahydronaphthaleneazonaphthalene or acetoacetamide series,W.sub.1 is a direct bond or a divalent bridging radical,each W.sub.Type: GrantFiled: February 28, 1986Date of Patent: April 11, 1989Assignee: Sandoz, Ltd.Inventors: Werner Baumann, Joseph V. Diest, Herbert Eichenberger, Max Oppliger
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Patent number: 4754021Abstract: Methine-azo compounds of the formulae ##STR1## in which A is the complement to a heterocyclic 5- or 6-membered ring which has a quaternized N atom as a ring member, which can contain further hetero atoms and which can be substituted and/or be fused with carbocyclic or heterocyclic rings,R is hydrogen, cyano or C.sub.2 -C.sub.3 -alkylene which is bonded to an N atom of ring A to form a 5- or 6-membered ring,B is substituted or unsubstituted phenylene or naphthylene,m and n independently of each other are the numbers 1 or 2, in the formula (I) at least one of the two symbols m and n being the number 2 and where in the case m=2 the two B's are identical or different,KK is the radical of a coupling componentX.sup..crclbar. is an anion and Y is a bridge member. These compounds can be used for dyeing and printing in particular polyacrylonitrile, acid-modified polyester and especially paper.Type: GrantFiled: August 21, 1985Date of Patent: June 28, 1988Assignee: Ciba-Geigy CorporationInventor: Peter Mockli
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Patent number: 4742160Abstract: Metal-free compounds of the formula ##STR1## and 1:1 and 1:2 metal complexes thereof, and salts of the metal-free compounds and 1:1 and 1:2 metal complexes, whereR is hydrogen, --SO.sub.3 H or --NR.sub.5 R.sub.6 ;R.sub.a is hydrogen or --NR.sub.5 R.sub.6 ;R.sub.1 is hydrogen, halogen, --OH, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or --SO.sub.3 H;R.sub.3 is hydrogen or C.sub.1-4 alkyl;R.sub.4 is halogen, --OH, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenyl, --NH.sub.2, an aliphatic, cycloaliphatic or aromatic amino group, a heterocyclic amino group containing 1 to 3 hereto atoms or a hydrazino group,R.sub.5 is hydrogen or C.sub.1-4 alkyl; andR.sub.6 is an organic radical, are useful as cationic dyes for dyeing and printing fibers, threads and textile materials comprising, for example, a natural or regenerated cellulosic material such as cotton, a modified synthetic polyamide or polyester, and a homo- or co-polymer of acrylonitrile or 1,1-dicyanoethylene, bast fibers such as hemp and particularly paper and leather.Type: GrantFiled: February 28, 1986Date of Patent: May 3, 1988Assignee: Sandoz Ltd.Inventors: Jacky Dore, Reinhard Pedrazzi
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Patent number: 4742161Abstract: Disazo and trisazo compounds of the formula ##STR1## and salts thereof, wherein in each B is independently hydrogen; C.sub.1-4 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 cyloalkyl substituted by 1 to 3 C.sub.1-4 alkyls; phenyl (C.sub.1-3 alkyl); phenyl (C.sub.1-3 alkyl) the phenyl group of which is substituted by 1 to 3 substituents selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy and halo; --A--NH--R.sub.2 ; --A.sub.2 --N(R.sub.7).sub.2 ; --A.sub.N.sup..crclbar. (R.sub.8).sub.2 R.sub.9 A.sup..sym. or --N(R.sub.7).sub.2,whereinA, A.sub.1, A.sub.2 and R.sub.7 -R.sub.9 are as defined in the specification,each R is independently hydrogen; amino C.sub.1-4 alkyl; C.sub.5-6 cycloalkyl; C.sub.5-6 cycloalkyl substituted by 1 or 2 C.sub.1-4 alkyls; phenyl; benzyl; phenylethyl; or phenyl, benzyl or phenylethyl the phenyl group of which is substituted by 1 or 2 substituents selected from methyl, ethyl, methoxy and ethoxy,each R.sub.5 is independently hydrogen or C.Type: GrantFiled: May 20, 1985Date of Patent: May 3, 1988Assignee: Sandoz Ltd.Inventor: Jacky Dore
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Patent number: 4686285Abstract: (i) Metal-free compounds of the formula ##STR1## (ii) tautomers thereof, (iii) 1:1 and 1:2 metal complexes of (i) and (ii),(iv) salts of (i), (ii), and (iii), and(v) mixtures of (i), (ii), (iii), and (iv),wherein the symbols are as defined in the Specification, are useful as dyes for, for example, polymers and copolymers of acrylonitrile, polyesters modified to contain acid groups, polyamides such as wool, leather, cotton, bast fibers such as hemp, flax, sisal jute, coir and straw, regenerated cellulose, glass fibers and paper (those wherein R.sub.o is other than hydrogen) or as intermediates for the synthesis of dyes.Type: GrantFiled: February 8, 1985Date of Patent: August 11, 1987Assignee: Sandoz Ltd.Inventor: Reinhard Pedrazzi