Sulfonated Azo Patents (Class 8/681)
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Patent number: 7078497Abstract: The dyes of formula (1) according to claim 1 and the copper complexes of dyes of formula (2) according to claim 9 or the mixtures of mono-copper complex with the bis-copper complex are excellently suitable for dyeing paper with good light-fastness properties.Type: GrantFiled: December 19, 2001Date of Patent: July 18, 2006Assignee: Ciba Specialty Chemicals CorporationInventors: Adolf Käser, Holger Lautenbach
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Patent number: 6997978Abstract: The present invention is drawn to magenta dye blends and magenta ink-jet inks that can be used in ink sets for creating photo quality images. The dye blend can comprise a nickel-containing azo dye blended with a rhodamine dye at a 1:80 to 125:4 weight ratio.Type: GrantFiled: July 18, 2003Date of Patent: February 14, 2006Assignee: Hewlett-Packard Development Company, L.P.Inventors: Alexey S Kabalnov, Charles G. Dupuy, Patricia A Wang
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Patent number: 6991676Abstract: The present invention is drawn to dye sets for formulating ink-jet ink sets, and to specific ink sets. The dye set can comprise cyan colorant including a phthalocyanine dye; magenta colorant including a copper- or nickel-containing azo dye; and yellow colorant including at least one of Yellow 1189 dye and Yellow 104 dye yellow colorant having the structure Formula 1: wherein R1 is H, SO3M, COOM, or SO2NH2; and wherein R2 is H, SO3M, COOM, or SO2NH2; and wherein R3 is H or CH3; and wherein n and m are 2, 3, 4, 5 or 6; and wherein M is H, Na, Li, K, ammonium, ammonium substituted with alkyl or combinations thereof. Optionally, a cyan triarylmethine dye such as Acid Blue 9, or another similar cyan dye, can be blended with the phthalocyanine dye; a rhodamine dye can be blended with the copper- or nickel-containing azo dye; and/or Acid Yellow 17 or Acid Yellow 23 can be blended with Formula 1.Type: GrantFiled: July 18, 2003Date of Patent: January 31, 2006Assignee: Hewlett-Packard Development Company, L.P.Inventors: Alexey S Kabalnov, Charles G. Dupuy, Luanne J. Rolly, Naomi Oak, Patricia A Wang
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Patent number: 6984723Abstract: Use of the mono-copper complex of a dye of formula (1) wherein Z1, Z2, R1, R2, R3, R4, X, n and m are as defined in the claims, and mixtures thereof with the bis-copper complex of such a dye, for dyeing natural and synthetic material.Type: GrantFiled: December 19, 2001Date of Patent: January 10, 2006Assignee: Ciba Specialty Chemicals CorporationInventor: Adolf Käser
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Patent number: 6930178Abstract: The present invention relates to novel 1:2 chromium complex dyes, processes for their preparation and their use for dyeing or printing fiber materials containing hydroxyl groups or containing nitrogen. The present invention relates to a 1:2 chromium complex dye of formula (I): wherein all substituents are as defined in the claims, a process for their preparation and their use for dyeing or printing fiber materials containing hydroxyl groups or containing nitrogen.Type: GrantFiled: September 26, 2002Date of Patent: August 16, 2005Assignee: Clariant Finance (BVI) LimitedInventors: Rainer Nusser, Georg Schoefberger, Reinhard Pedrazzi
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Patent number: 6844428Abstract: The invention relates to the use of disazo compounds according to formula (I) wherein all substituents are as defined in claim 1 salts thereof and mixtures of these compounds for dyeing or printing organic substrates, to novel compounds, to the process for the production of these compounds and to substrates dyed or printed by these compounds.Type: GrantFiled: December 3, 2001Date of Patent: January 18, 2005Assignee: Clariant Finance (BVI) LimitedInventors: Ludwig Hasemann, Friedrich Lehr
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Patent number: 6767394Abstract: A composition comprising a dye of Formula (I) and a dye of Formula (II) or salts thereof, and use of the composition in ink jet printingType: GrantFiled: September 4, 2002Date of Patent: July 27, 2004Assignee: Avecia LimitedInventors: Andrew Paul Shawcross, Mark Holbrook, Paul Nicholas Ewing
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Patent number: 6727351Abstract: Azoxy dyes of the general formula I in the form of the free acid where n is 0 or 1, each R1 is selected from the group consisting of methoxy, hydroxyl and carboxyl, each R2 is selected from the group consisting of carboxyl, amino, C1-C4-alkylamino, allylamino, benzylamino and methoxycarbonylmethylamino, and the phenyl rings A may additionally be substituted by C1-C8-alkyl, unsubstituted or methyl- or halogen-substituted phenyl, hydroxyl, amino, nitro, halogen, carboxyl, N-benzylcarbamoyl, unsubstituted or nitro-, halogen-, C1-C4-alkoxy- or acetoxy-substituted phenylcarbamoyl and naphthylcarbamoyl or be benzofused, their copper complexes, a process for preparing the copper complex dyes, azoxy dyes of the formula I in their partially or completely deacylated form, their copper complexes, colorants comprising these azoxy dyes and/or their copper complexes and also their use for dyeing and printing natural or synthetic substrates.Type: GrantFiled: September 13, 2001Date of Patent: April 27, 2004Assignee: BASF AktiengesellschaftInventors: Rainer Tresch, Karl-Heinz Etzbach, Rüdiger Sens, Claudia Kräh
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Patent number: 6712862Abstract: Granular compacts (G) of a mixture of (A) at least one water-soluble dye or optical brightener, and (B) extender and, optionally, (C) at least one hydrophilic surfactant and/or (D) further additives, additionally containing (E) a dust-binding oil, are low-dust dry formulations of high bulk density which feature good dissolution, transportation and storage properties and are outstandingly suitable for the dyeing of the respective substrates.Type: GrantFiled: May 1, 2000Date of Patent: March 30, 2004Assignee: Clariant Finance (BVI) LimitedInventors: Roland Grimm, Claude Haldimann, Werner Schumann
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Publication number: 20030226221Abstract: A compound which can be used as a dye and is represented by the following general formulae (I), (II) and (III). In the general formulae, A and B each independently represents a monovalent heterocyclic group bonded to an azo group by a carbon atom of the monovalent heterocyclic group; m and n each independently represents one of 0 and 1; and M represents one of a hydrogen atom and a monovalent positive ion.Type: ApplicationFiled: January 24, 2003Publication date: December 11, 2003Inventors: Hisashi Mikoshiba, Tadashi Omatsu, Makoto Suzuki, Koushin Matsuoka, Masuji Motoki
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Patent number: 6660048Abstract: The aqueous dye solutions of the composition shown in claim 1 are distinguished by a good storage stability and are suitable for dyeing paper in red color shades.Type: GrantFiled: April 17, 2001Date of Patent: December 9, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: Alfred Höhener, Roland Frick, Adolf Kaeser
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Publication number: 20030136301Abstract: A composition comprising a dye of Formula (I) and a dye of Formula (II) or salts thereof, and use of the composition in ink jet printing.Type: ApplicationFiled: September 4, 2002Publication date: July 24, 2003Inventors: Andrew Paul Shawcross, Mark Holbrook, Paul Nicholas Ewing
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Patent number: 6511535Abstract: The invention relates to a method for printing fibrous textile materials using the ink-jet printing technique, wherein the fibrous materials are printed with an aqueous ink that comprises at least one acid dye according to claim 1 and that has a viscosity of from 1 to 40 mPa·s.Type: GrantFiled: January 3, 2001Date of Patent: January 28, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: Roger Lacroix, Peter Scheibli, Mickael Mheidle
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Patent number: 6365719Abstract: Compounds of formula (I) with the meanings of D, R1, R2, X and Y as given in claim 1 can be used as paper dyes or direct dyes or for the preparation of ink-jet inks.Type: GrantFiled: March 27, 2000Date of Patent: April 2, 2002Assignee: Clariant Finance (BVI) LimitedInventor: Friedrich Lehr
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Patent number: 6254671Abstract: 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: GrantFiled: November 15, 1999Date of Patent: July 3, 2001Assignee: Engelhard CorporationInventor: Byron G. Hays
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Patent number: 6221114Abstract: Dye salts which are free from fiber-reactive radicals and have the formula where Chr is an (m+n)-valent radical of a chromophore from the series of the metal-free or metal-containing phthalocyanines, of the quinacridones, of the mono-, dis- or polyazo dyes, of the anthraquinones or copper formazans, Ar is phenyl or naphthyl each of which is unsubstituted or substituted, x⊕ is a metal cation or ammonium ion, y⊕ is a proton, metal cation or ammonium ion, m is 1 to 6 and n is 1 to 6, the sum of m and n being not more than 7, are used in methods of dyeing or printing polymeric material and in dye preparations.Type: GrantFiled: September 17, 1999Date of Patent: April 24, 2001Assignee: BASF AktiengesellschaftInventors: Frank Würthner, Rüdiger Sens, Günther Seybold, Karl-Heinz Etzbach
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Patent number: 6130320Abstract: Disazo dyes of formula (I) where one of the two symbols X.sup.1 and X.sup.2 means hydroxy and the other amino and R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are as defined in the specification. The invention also relates to sulphonamides as their intermediate products and to the use of the dyes for the dyeing of natural and synthetic substrates.Type: GrantFiled: July 22, 1998Date of Patent: October 10, 2000Assignee: BASF AktiengesellschaftInventors: Gunther Lamm, Helmut Reichelt, Gerhard Wagenblast
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Patent number: 6120561Abstract: Process for the preparation of low-salt liquid dyestuff preparations, characterized in that they are obtained by:a) diazotization of an aromatic amine,b) 2-fold coupling of the diazo component obtained according to a) to I-acid-urea, in the presence of an inorganic base and in the absence of an organic base,c) desalination and, if appropriate, concentration by means of a pressure permeation of the reaction mixture obtained according to b), so that an inorganic salt content of less than 1% by weight is achieved.Type: GrantFiled: April 17, 1997Date of Patent: September 19, 2000Assignee: Bayer AktiengesellschaftInventors: Peter Wild, Volker Paulat, Wolfgang Frank, Shaun Murphree
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Patent number: 6084078Abstract: The novel disazo dyestuffs of the formula (I) in which the substituents and indices have the meanings given in the description, are outstandingly suitable for dyeing cellulosic materials in red-violet to blue brilliant color shades.Type: GrantFiled: December 17, 1997Date of Patent: July 4, 2000Assignee: Bayer AktiengesellschaftInventor: Winfried Mennicke
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Patent number: 6080209Abstract: Stable aqueous dye compositions containing at least one anionic colorant and at least one pigment and a polyanionic thickening agent. The dye compositions may be used to dye leather.Type: GrantFiled: September 25, 1998Date of Patent: June 27, 2000Assignee: BASF AktiengesellschaftInventors: Matthias Wiesenfeldt, Johannes Peter Dix, Rudolf Paulus, Manfred Herrmann
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Patent number: 6031083Abstract: The new disazo dyestuffs of the formula (I) ##STR1## wherein the substituents and the indices have the meanings given in the description,wherein more than 25 equivalent % of all the M cations in the molecule are alcohol ammonium radicals of the formula .sup..sym. NR.sub.1 R.sub.2 R.sub.3 R.sub.4 whereinR.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently of one another represent hydrogen, C.sub.1 -C.sub.4 -alkyl and C.sub.2 -C.sub.4 -hydroxyalkyl, with the proviso that at least one of the radicals R.sub.1 -R.sub.4 denotes C.sub.2 -C.sub.4 -hydroxyalkyl,are excellently suitable for dyeing cellulose-containing materials, and in particular paper, and are distinguished by high degrees of fastness.Type: GrantFiled: March 19, 1999Date of Patent: February 29, 2000Assignee: Bayer AktiengesellschaftInventors: Klaus Kunde, Wolfgang Zarges
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Patent number: 5922085Abstract: A process of preparing a dye composition and a resultant dye composition. The process includes preparing a mixture comprising a triphenylmethane dye and oxidation products by reacting methylenedianiline, aniline, an oxidation catalyst, and an oxidant; separating the oxidation products from the triphenylmethane dye to produce an aqueous solution of oxidation products; treating the solution of oxidation products with a basic compound; separating unreacted aniline from the solution of oxidation products and forming a mixture of oxidation products; and sulfonating the mixture of oxidation products to form a dye composition.Type: GrantFiled: September 30, 1997Date of Patent: July 13, 1999Assignee: BASF CorporationInventors: Gray D. Ellis, Belinda J. DiMarcello, Debra J. Bradshaw
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Patent number: 5883234Abstract: The novel process for dyeing cellulosic materials with disazo dyestuffs of the formula ##STR1## in which the substituents NHR.sup.1 and NHR.sup.2 are in each case in the 6- and/or 7-position and R.sup.1, R.sup.2, m, n, p and q have the meaning given in the description, produces blue dyeings with very good fastness properties.Type: GrantFiled: September 18, 1997Date of Patent: March 16, 1999Assignee: Bayer AktiengesellschaftInventors: Winfried Mennicke, Klaus Kunde
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Patent number: 5834602Abstract: Disazo dyes of the formula ##STR1## where the ring A may be benzofused,X is hydrogen or C.sub.1 -C.sub.4 -alkyl,R.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl, halogen, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl or hydroxysulfonyl,R.sup.2 is hydrogen, C.sub.1 -C.sub.4 -alkyl, halogen, carboxyl or C.sub.1 -C.sub.4 -alkoxycarbonyl, or R.sup.1 and R.sup.2 together are a radical of the formula L--NZ--CO, where L is methylene or carbonyl and Z is substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or substituted or unsubstituted phenyl, andR.sup.3 is hydrogen, C.sub.1 -C.sub.4 -alkyl, hydroxyl, C.sub.1 -C.sub.4 -alkoxy, phenoxy, C.sub.1 -C.sub.4 -alkanoyloxy or benzoyloxy,are useful for dyeing natural or synthetic substrates.Type: GrantFiled: January 26, 1998Date of Patent: November 10, 1998Assignee: BASF AktiengesellschaftInventors: Gunther Lamm, Helmut Reichelt
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Patent number: 5808016Abstract: The novel disazo dyestuffs of the formula (I) ##STR1## in which the substituents and indices have the meaning given in the description, are outstandingly suitable for dyeing cellulosic materials, in particular paper, and are distinguished by good fastness properties.Type: GrantFiled: September 17, 1997Date of Patent: September 15, 1998Assignee: Bayer AktiengesellschaftInventor: Klaus Kunde
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Patent number: 5704951Abstract: A solid or dissolved dye mixture of azo dyes having fiber-reactive groups of the vinyl sulfone series, yielding dyeings of blue color shade, comprising one or more copper formazane dyes of the general formula (1) shown and defined in claim 1, one or more disazo dyes of the general formula (2) shown and defined in claim 1, and one or two monoazo dyes of the general formula (3) shown and defined in claim 1, respectively in the description part of the patent application, which dye mixtures are suitable for dyeing hydroxy- and/or caroboxamido groups containing materials, in particular fiber materials, such as cellulose fibers, for example cotton, wool and synthetic polyamide fibers, also together with other suitable dyes in trichromatic dyeing.Type: GrantFiled: April 1, 1996Date of Patent: January 6, 1998Assignee: Hoechst AktiengesellschaftInventors: Daniele Negri, Andreas Von Der Eltz, Werner Hubert Russ, Bengt-Thomas Grobel
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Patent number: 5700296Abstract: An azo compound of the following formulae (I) or (II): ##STR1## wherein Q.sub.1 represents a phenyl group or a naphthyl group, Q.sub.2 represents a phenyl group; R represents hydroxy group; R.sub.1 and R.sub.2 each independently represent a hydrogen atom, a hydroxy group, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group or a halogen atom; R.sub.3 and R.sub.4 each independently represent a hydrogen atom, a hydroxy group, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group or a substituted amino group; and X represents --NH--, --NHCO-- or --N.dbd.N--; or a salt thereof;and a polarizing film containing the same.Type: GrantFiled: February 20, 1996Date of Patent: December 23, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Kazuya Ogino, Kaneo Yokoyama, Narutoshi Hayashi, Takashi Omura, Setsuko Yamamoto
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Patent number: 5697985Abstract: This invention relates to a process for the preparation of storage-stable dye dispersions of alkali metal salts of anionic azo direct dyes by(a) preparing an aqueous slurry of an alkali metal salt of an azo direct dye, said salt having a solubility in water at 25.degree. C. of about 0.1 to about 15% by weight, by azo coupling one or more aromatic diazonium salts with one or more couplers while maintaining a pH of at least about 5 by adding a basic alkali metal compound in the absence of a nitrogen-containing base;(b) optionally, stirring the aqueous slurry at a temperature of about 5.degree. C. to about 100.degree. C. for up to about six hours;(c) optionally, adjusting the temperature of the aqueous slurry to about 5.degree. C. to about 40.degree. C.; and(d) adding to the aqueous slum/a viscosity enhancing agent in an amount sufficient to obtain a viscosity, determined at a temperature of about 20.degree. to about 25.degree. C.Type: GrantFiled: May 24, 1996Date of Patent: December 16, 1997Assignee: Bayer CorporationInventors: James J. Good, Tanya T. Harper, Samuel S. Murphree, John G. Skabardonis
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Patent number: 5668259Abstract: Compounds of the formula ##STR1## iron complexes thereof and mixtures of such iron complexes, wherein D is a monocyclic or bicyclic aromatic diazo component radical of the benzene series containing one --SO.sub.3 M group or is ##STR2## R.sub.1 is hydrogen, methyl or ethyl, and R.sub.4 is hydrogen, chloro or C.sub.1-2 alkyl,wherein R' is hydrogen, C.sub.1-4 alkyl, C.sub.2-4 hydroxyalkyl, methoxy(C.sub.2-4 alkyl) or ##STR3## R" is hydrogen, C.sub.1-4 alkyl, C.sub.2-4 hydroxyalkyl or methoxy(C.sub.2-4 alkyl), or--NR'R" is a saturated 5- or 6-membered ring,R.sub.5 is hydrogen, chloro or C.sub.1-2 alkyl, andX is hydrogen or hydroxy,wherein each R.sub.2 is independently hydrogen, chloro, hydroxy, C.sub.1-2 alkyl, C.sub.1-2 alkoxy or --SO.sub.2 NR.sub.o R.sub.o, andeach R.sub.3 is independently hydrogen, C.sub.1-2 alkyl, C.sub.1-2 alkoxy, --COOM, trifluoromethyl or --NR"'R"",wherein each R"' and R"" is independently C.sub.1-4 alkyl, C.sub.2-4 hydroxyalkyl, methoxy(C.sub.2-4 alkyl) or carbamoyl(C.sub.Type: GrantFiled: May 15, 1995Date of Patent: September 16, 1997Assignee: Clariant Finance (BVI) LimitedInventors: Jordi Berenuger Barra, Herbert Holliger, Jose Rocas Sorolla
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Patent number: 5665124Abstract: Dyeings having improved properties are obtained with a dyestuff of the following formula ##STR1## wherein the substituents have the meaning given in the description.Type: GrantFiled: October 20, 1995Date of Patent: September 9, 1997Assignee: Bayer AktiengesellschaftInventors: Horst Jager, Joachim Wolff
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Patent number: 5650497Abstract: Azo dyes of the formula ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 independently of one another are hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen,R.sub.6 is hydrogen or C.sub.1 -C.sub.4 Alkyl,X is --C.sub.1 -C.sub.4 alkylene-O--C.sub.1 -C.sub.4 alkyl andY is hydrogen; unsubstituted or hydroxy- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.4 -alkonoyl or C.sub.1 -C.sub.4 alkoxycarbonyl; a radical of the formula --CH.sub.2 --CH.dbd.CH.sub.2 ;C.sub.1 -C.sub.4 alkylsulfonyl; or unsubstituted or C.sub.1 -C.sub.4 alkyl-, C.sub.1 -C.sub.4 alkoxy- or halogen-substituted phenylsulfonyl, produce dyeings with good fastness properties on fibre materials containing nitrogen or containing hydroxyl groups.Type: GrantFiled: July 15, 1996Date of Patent: July 22, 1997Assignee: Ciba-Geigy CorporationInventors: Jean-Marie Adam, Peter Sutter
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Patent number: 5632783Abstract: Reactive dye mixtures comprising the dyes of the formulae ##STR1## where Kat.sup..sym. is a cation, L is C.sub.2 -C.sub.4 -alkylene, and X.sup.1, X.sup.2, Y.sup.1 and Y.sup.2 are each vinyl or a radical of the formula C.sub.2 H.sub.4 -Q, where Q is a group detachable under alkaline reaction conditions, in a weight ratio of from 20:80 to 90:10, are useful for dyeing or printing hydroxyl-containing or nitrogenous organic substrates.Type: GrantFiled: February 28, 1996Date of Patent: May 27, 1997Assignee: BASF AktiengesellschaftInventors: Reinhold Krallmann, Manfred Sulflow
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Patent number: 5611821Abstract: A black reactive dye composition comprising a black reactive dye of the formula (I) and multiple mono ##STR1## azo reactive dye. The black reactive dye composition is suitable for exhaust dyeing, printing, discharge printing and continuous dyeing.Type: GrantFiled: October 19, 1995Date of Patent: March 18, 1997Assignee: Everlight USA, Inc.Inventors: Huei C. Huang, Sheue R. Lee
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Patent number: 5597387Abstract: The present invention relates to water-soluble polyazo dyestuffs of the general formula I ##STR1## wherein Y, Z, m and M.sup..sym.1 to M.sup..sym.4 are as defined in claim 1, processes for dyeing leather and paper with the polyazo dyestuffs, and recording liquids and inks containing the polyazo dyestuffs.Type: GrantFiled: November 9, 1995Date of Patent: January 28, 1997Assignee: Hoechst AGInventors: Wolfgang Bauer, Dieter Baumgart, Walter Zoller
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Patent number: 5559217Abstract: The dyestuffs of the formula ##STR1## in which A, R.sub.1, M and n are as defined in claim 1, are suitable for dyeing paper with good light-fastness.Type: GrantFiled: October 2, 1995Date of Patent: September 24, 1996Assignee: Ciba-Geigy CorporationInventor: Adolf K aser
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Patent number: 5545725Abstract: Disazo dyes are disclosed which are particularly suitable for dyeing paper.Paper is dyed with these dyes in greenish-yellow or yellow to red shades of good fastness properties.Type: GrantFiled: November 10, 1994Date of Patent: August 13, 1996Assignee: Ciba-Geigy CorporationInventors: Adolf K aser, Willy Stingelin
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Patent number: 5527887Abstract: Disazo acid dyestuff with the following general formula: ##STR1## wherein R represents H, C.sub.n H.sub.2n+1 wherein n is a natural number between 1 and 4, or (CH.sub.2).sub.m OR' wherein m is a natural number between 1 and 4 and R' represents C.sub.p H.sub.2p+1 wherein p is an integral number between 0 and 4; wherein R" represents H, CN or COOR wherein R has the same definition as above. The sulfo group may be at any position of the benzene ring.Type: GrantFiled: January 12, 1995Date of Patent: June 18, 1996Assignee: Allied Industrial Corp., Ltd.Inventors: Hsien-Chyang Tsien, Chen-Kung Chi, Hung Chang
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Patent number: 5527889Abstract: Azo dyes of formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, unsubstituted C.sub.2 -C.sub.4 alkanoylamino or C.sub.2 -C.sub.4 alkanoylamino which is substituted by hydroxy, sulfo or sulfato, or are halogen or sulfo,R.sub.3, R.sub.4 and R.sub.5 are each independently of one another hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen or sulfo,R.sub.6 is hydrogen, C.sub.1 -C.sub.4 alkyl, halogen, sulfo, unsubstituted C.sub.2 -C.sub.4 alkanoylamino or C.sub.2 -C.sub.4 alkanoylamino which is substituted by hydroxy, sulfo or sulfato, or is a radical of formula --O--Y, wherein Y is hydrogen, C.sub.1 -C.sub.8 alkyl or C.sub.1 -C.sub.8 alkyl which is substituted by hydroxy, C.sub.1 -C.sub.4 alkoxy, sulfo or sulfato,R.sub.7 is hydrogen, C.sub.1 -C.sub.8 alkyl or hydroxy-substituted C.sub.1 -C.sub.8 alkyl, or C.sub.2 -C.sub.8 alkyl which is interrupted in the chain by the group --O-- or ##STR2## and X is C.sub.1 -C.Type: GrantFiled: April 17, 1995Date of Patent: June 18, 1996Assignee: Ciba-Geigy CorporationInventors: Jurgen Schaetzer, James C. Posey
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Patent number: 5519121Abstract: Novel dyestuffs of the formula (I) ##STR1## in which DK denotes a radical of the formula ##STR2## where m is 1 or 2 and DK' denotes a radical of the formula ##STR3## where n is 1 or 2 R.sub.1 represents hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkyl,R.sub.2 represents hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,R.sub.3 represents substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -acylamino andR.sub.4 represents substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl.have now been found.The invention also relates to a process for their preparation and to their use for dyeing/coloring and printing textiles and paper, in particular in printing inks containing these dyestuffs.Type: GrantFiled: February 24, 1995Date of Patent: May 21, 1996Assignee: Bayer AktiengesellschaftInventors: Gerd-Friedrich Renner, Peter Wild, Karin Hassenruck
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Patent number: 5514783Abstract: 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 groupand in whichthe 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: GrantFiled: April 28, 1995Date of Patent: May 7, 1996Assignee: Sandoz Ltd.Inventors: Jordi B. Barra, Jose R. Sorolla
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Patent number: 5495003Abstract: The disazo dyestuffs and mixtures thereof, of the general formula I ##STR1## wherein the symbols R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and M possess the significances given in claim 1, are eminently suitable for dyeing or printing organic substrates containing hydroxyl, thiol or amido groups, especially cotton or paper.Type: GrantFiled: February 27, 1994Date of Patent: February 27, 1996Assignee: Sandoz Ltd.Inventors: Reinhard Pedrazzi, Ulrich Zirngibl
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Patent number: 5489671Abstract: A trisazo compound represented by the following formula (1) in the free acid form: ##STR1## wherein Q' is phenylene group, Q.sup.2 is phenyl or naphtyl group, one of the A and B is a hydroxy group and the other is an amino group, K is 1 or 2, one of m and n is 1 and the other is 0, X and Y independently of one another are each --OR.sup.1, --SR.sup.2, --NR.sup.3 R.sup.4 or ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently of one another are each a hydrogen atom, an alkyl, phenyl or naphthyl group; r is 1 or 2; and Z is --CH.sub.2 --, --O--, --SO.sub.2 -- or --NR.sup.5 -- wherein R.sup.5 is a hydrogen atom or C.sub.1 -C.sub.4 alkyl group;a method for dyeing fiber material, paper or leather by using the trisazo compound;and an ink which contains the trisazo compound and which is excellent in storage stability and can give a clear black printed image having excellent water resistance and light fastness.Type: GrantFiled: September 27, 1994Date of Patent: February 6, 1996Assignee: Sumitomo Chemical Company, LimitedInventors: Kazuya Ogino, Yuriko Tamura, Takashi Omura, Mahito Fujita, Hideo Kawashita, Koji Aburada
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Patent number: 5487761Abstract: The dyestuffs of the formula ##STR1## in which A, R.sub.1, M and n are as defined in claim 1, are suitable for dyeing paper with good light-fastness.Type: GrantFiled: April 20, 1994Date of Patent: January 30, 1996Assignee: Ciba-Geigy CorporationInventor: Adolf Kaser
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Patent number: 5466527Abstract: Stain-resistant nylon, especially cationic-dyeable carpet nylon, is prepared by dyeing cationic-dyeable nylon fibers with acid or premetallized dye. Lightfastness and depth of shade of an apparent value equal to acid dyeable nylons is obtained with superior stain resistance equal to commercially available solution dyed nylon carpeting.Type: GrantFiled: November 3, 1994Date of Patent: November 14, 1995Assignee: Burlington IndustriesInventor: William G. Jenkins
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Patent number: 5456728Abstract: An improved reactive dyestuff mixture comprises at least one monochlorotriazine dyestuff 1 and at least one monofluorotriazine dyestuff 2 and/or fluorochloropyrimidine dyestuff 3, and if appropriate additional dyestuffs having the formulae given in the description.Type: GrantFiled: December 14, 1994Date of Patent: October 10, 1995Assignee: Bayer AktiengesellschaftInventors: Max Schwarz, Joachim Grutze, Dietrich Hildebrand, Joachim Wolff, Frank-Michael Stohr
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Patent number: 5445654Abstract: The disclosed black dye mixtures contain 50 to 95% by weight of one or more disazo dyes of the formula (1) and 5 to 50% by weight of one or more monoazo dyes of the formula (2) ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6, identical to or different from each other, are each hydrogen, methyl, ethyl, methoxy, ethoxy, sulfo or carboxy,Y is in each instance independently of the others vinyl, .beta.-chloroethyl, .beta.thiosulfatoethyl or .beta.-sulfatoethyl, andM is hydrogen or an alkali metal.Type: GrantFiled: November 24, 1993Date of Patent: August 29, 1995Assignee: Hoechst AktiengesellschaftInventors: Kurt Hussong, Werner H. Russ, Karl Krieger
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Patent number: 5423100Abstract: Novel azo compounds having the specific structural formula (1) or (3) set out below, water-soluble dyes containing the compounds, and polarizing films containing the water-soluble dyes: ##STR1## wherein R.sub.1 represents a hydrogen or halogen atom or a hydroxyl, C.sub.1-2 alkyl, C.sub.1-2 alkoxy, C.sub.1-2 acylamino, cyano, carboxyl or sulfonic acid group; R.sub.3 and R.sub.8 individually represent a hydrogen atom or a hydroxyl, C.sub.1-2 alkyl or C.sub.1-2 alkoxy group; R.sub.2 and R.sub.4 individually represent a hydrogen atom or a hydroxyl, C.sub.1-2 alkyl, C.sub.1-2 alkoxy or C.sub.1-2 acylamino group; R.sub.5 represents a hydrogen atom or a carboxyl or C.sub.1-2 alkoxy group; R.sub.6 represents a hydrogen atom, a hydroxyl, amino, methylamino, .beta.-hydroxyethylamino or C.sub.1-2 acylamino group, or a phenylamino or benzoylamino group which the phenyl nucleus may be substituted by one or more nitro, amino, hydroxyl, C.sub.1-2 alkyl, carboxyl and/or sulfonic acid groups and/or chlorine atoms; R.sub.Type: GrantFiled: July 23, 1993Date of Patent: June 13, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tsutami Misawa, Akira Ogiso, Rihoko Imai, Hisato Itoh
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Patent number: 5411556Abstract: There is described a process for dyeing leather with the dye of the formula ##STR1##Type: GrantFiled: October 14, 1993Date of Patent: May 2, 1995Assignee: BASF AktiengesellschaftInventors: Johannes P. Dix, Gunther Lamm, Helmut Reichelt, Georg Zeidler
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Patent number: 5401834Abstract: Complexes of the formula ##STR1## which are in free acid or salt form, and mixtures thereof, wherein each ofR.sub.1 and R.sub.3 is independently hydrogen, C.sub.1-4 alkyl or C.sub.1-4 alkyl monosubstituted by hydroxy, amino, sulfo or carboxy,each ofR.sub.2 and R.sub.4 is independently hydrogen; C.sub.1-4 alkyl; C.sub.1-4 alkyl monosubstituted by hydroxy, amino, sulfo or carboxy; --COR.sub.5 ; --COOR.sub.6 or --CONHR.sub.7,M is chromium or cobalt, andM.sub.K.sup..sym. is hydrogen or a non-chromophoric cation, useful for dyeing or printing, materials such as natural and synthetic polyamides and particularly artificially produced oxide layers on aluminum and aluminum alloys.Type: GrantFiled: June 22, 1993Date of Patent: March 28, 1995Assignee: Sandoz Ltd.Inventor: Klaus Koerte
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Patent number: 5401277Abstract: 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: May 17, 1994Date of Patent: March 28, 1995Assignee: Bayer AktiengesellschaftInventors: Wolfram Reddig, Karl-Josef Herd