Monosulfonated Patents (Class 8/683)
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Patent number: 8349029Abstract: The present invention relates to azo dyes of the formula (1) in which R, M, and Y are defined as stated in claim 1, to dye mixtures comprising them, to processes for preparing them, and to their use.Type: GrantFiled: January 30, 2012Date of Patent: January 8, 2013Assignee: DyStar Colours Deutschland GmbHInventors: Jörg Wörner, Andreas Schrell
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Patent number: 7909892Abstract: The present invention relates storage stable aqueous dye solutions comprising a) 5 to 30% by weight of a dye of the formula in which K is a residue of a coupling component of the acetoacetanilide, pyridone, pyrazolone or pyrimidine series and M is hydrogen, an alkali metal or alkaline earth metal, ammonium or alkyl ammonium, b) 0.05 to 5% by weight of one or more compounds of the formula or a residue of the formula in which A, X, Y, R, P and Q are defined herein, c) an organic or an inorganic base or mixtures thereof, d) if desired, further additives and e) water, a process for their preparation and the use thereof for the dyeing, in particular of paper.Type: GrantFiled: January 21, 2003Date of Patent: March 22, 2011Assignee: BASF SEInventors: Holger Lautenbach, Adolf Käser, Michael Heneghan
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Publication number: 20110027548Abstract: Use of the customary dyes for the type of fibre in question and using the customary dyeing and/or printing processes for the type of fibre in question for minimally reducing, retaining or increasing the NIR reflectance, preferably increasing the NIR reflectance, in the region of electromagnetic radiation of wavelength 700 nm to 1100 nm of textile material in relation to the undyed and untreated textile material, characterized in that metal-free dyes are used.Type: ApplicationFiled: March 27, 2009Publication date: February 3, 2011Applicants: CLARIANT FINANCE (BVI) LIMITED, SCHOELLER TECHNOLOGIES AGInventors: Rainer Nusser, Martin Leiler, Roland Lottenbach, Hans-Juergen Huebner
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Patent number: 7217803Abstract: The present invention relates to azo dyes of formula (1) which are soluble in organic solvents, wherein R1 is —CN, —COOR5, —CONR6R7 or a heterocyclic ring, R2 is unsubstituted or substituted alkyl, unsubstituted or substituted aryl, —CF3, —COOR5, —CONR6R7 or —COR5, R3 is hydrogen, —SO3M, alkyl, alkoxy, alkylcarbonyl, —NO2 or halogen, R4 is substituted aryl, substituted heteroaryl or an aryl-N?N-aryl radical, wherein one or both of the aryl radicals in aryl-N?N-aryl is/are unsubstituted or substituted, or a radical heteroaryl-N?N-heteroaryl, wherein one or both of the heteroaryl radicals in heteroaryl-N?N-heteroaryl is/are unsubstituted or substituted, R5 is hydrogen, alkyl or unsubstituted or substituted aryl, R6 is hydrogen, alkyl or unsubstituted or substituted aryl, R7 is hydrogen, alkyl or unsubstituted or substituted aryl, M+ is a cation, n is a number 1, 2 or 3 and m is a number 1, 2 or 3, to a process for the preparation thereof and to the use thereof in the production of colored plastics or polymericType: GrantFiled: November 26, 2003Date of Patent: May 15, 2007Assignee: Ciba Specialty Chemicals CorporationInventors: Leonhard Feiler, Thomas Raimann, Thomas Eichenberger, Max Hügin
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Patent number: 7066969Abstract: The present invention relates to novel compounds of the formulae A, D1, D2, R1 and n are as defined in the description the compounds being in an internal or external salt form, or mixtures of compounds (1) and (2), a process for their preparation and preparations containing them used for dyeing paper.Type: GrantFiled: July 11, 2002Date of Patent: June 27, 2006Assignee: Ciba Specialty Chemicals CorporationInventors: Michael Lennartz, Dölf Käser, Sandra Weiss
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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: 20030177944Abstract: Compounds of the formula I 1Type: ApplicationFiled: February 13, 2003Publication date: September 25, 2003Inventors: Klaus Kunde, Stefan Ehrenberg
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Patent number: 6583273Abstract: This invention relates to dyes of formula wherein R1 is hydrogen, halogen, C1-C8alkyl, —NH—CO—C1-C4alkyl or phenyl, R2 is hydrogen, halogen, C1-C8alkyl, C1-C8alkoxy, —NH—CO—C1-C4alkyl or phenyl, R3 is hydrogen, C1-C8alkyl or phenyl, R4 is hydrogen, halogen or C1-C8alkyl, and X is —CO—, — COO—or —SO2—, and n is the number 1 or 2, to their preparation and to their use for dyeing or printing natural and synthetic materials, in particular synthetic polyamide fibre materials.Type: GrantFiled: May 4, 2000Date of Patent: June 24, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: Jean-Pierre Bacher, Jean-Marie Adam
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Patent number: 6515114Abstract: The invention relates to a Bunte salt azo dye composition comprising an azo dye containing at least one Bunte salt group. The resulting dye is water soluble material which is useful in the rapid dying of natural and synthetic fibers. The Bunte salt azo dye of the present invention can be used without requiring a mordanting step or a concurrent or pre-reducing step to condition fibers of animal hair to accept the dye to achieve strong color performance.Type: GrantFiled: June 10, 2002Date of Patent: February 4, 2003Assignee: Clariant Finance (BVI) LimitedInventors: James Myron Hanna, Jr., Guido Joseph Danhieux
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Patent number: 6241789Abstract: Process for dyeing or printing paper, films of plastic or fibre material containing hydroxyl groups or containing nitrogen with reactive dyes, which comprises using at least one reactive dye of the formula (1) from the following group a) and at least one reactive dye from the following groups b), c) and d): a) green- or blue-dyeing reactive dyes of the formula (1) b) blue-dyeing reactive dyes of the formula (2) or (3) c) red-dyeing reactive dyes of the formula (4) d) yellow- or orange-dyeing reactive dyes of the formula (5)Type: GrantFiled: April 3, 2000Date of Patent: June 5, 2001Assignee: Ciba Specialty Chemicals CorporationInventors: Peter Scheibli, Peter Aeschilmann, Urs Lehmann, Marcel Frick
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Patent number: 6191263Abstract: The invention relates to a novel crystal modification (&ggr;-modification ) of C.I. Pigment Red 53:2 of the formula (1) having the following characteristic reflections in the X-ray powder diffraction pattern: 2&THgr; d Relative intensity in % 4.4 20.2 49 5.8 15.4 100 8.8 10.0 23 10.3 8.6 25 10.9 8.1 33 12.2 7.3 15 13.9 6.4 16 15.4 5.8 15 16.7 5.3 28 17.6 5.0 16 18.4 4.8 18 18.6 4.8 18 19.7 4.5 20 20.8 4.3 18 23.2 3.8 48 24.0 3.7 21 24.8 3.6 37 25.2 3.5 34 26.6 3.3 19 27.3 3.3 19 27.9 3.2 12 29.3 3.Type: GrantFiled: June 21, 1999Date of Patent: February 20, 2001Assignee: Clariant GmbHInventors: Martin Ulrich Schmidt, Hans Joachim Metz
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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: 6045593Abstract: The invention is a composition of matter useful as an acid yellow dye having formula (I) ##STR1## wherein: X is hydrogen or SO.sub.3.sup.- M.sup.+ ; M.sup.+ Na.sup.+, Li.sup.+, K.sup.+, NH.sub.4.sup.+, or hydroxyalkylammonium of the formula [H--(OCH.sub.2 CH.sub.2).sub.n ].sub.p NH.sub.m, where n is 1 to 5, p is 1 to 3, and p+m is 4; R.sub.1 is hydrogen, a metal ion, an alkyl or C.sub.1-4, of hydroxyalkyl of C.sub.1-4, and combinations thereof; and R.sub.2 is an unsubstituted aromatic ring or a substituted aromatic ring having at least one substituent, provided that when one of the substituents is SO.sub.3.sup.- M.sup.+, X is hydrogen; and combinations thereof. The invention also includes a process for dyeing a material with this compound and the material so dyed.Type: GrantFiled: April 27, 1999Date of Patent: April 4, 2000Inventor: Howard L. Smith
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Patent number: 5993492Abstract: A dye mixture comprising at least two dyes of the formula (1) ##STR1## in which: D is phenyl or naphthyl which is substituted by 1, 2 or 3, sulfo groupsR.sup.A is aminocarbonyl of the formula --CO--NH.sub.2 or is a group of the formula (2) ##STR2## in which X is fluoro or hydroxyl,R.sup.1 is hydrogen, methyl, ethyl, methoxy or chloro,R.sup.2 is hydrogen, methyl, ethyl, methoxy or ethoxy,Y is vinyl or is ethyl substituted in .beta.-position by a substituent which can be eliminated by the action of an alkali to form the vinyl group, or is .beta.-hydroxyethyl, andn is zero or 1 (and if n is zero this group is hydrogen).Type: GrantFiled: November 13, 1998Date of Patent: November 30, 1999Assignee: DyStar Textilfarben GmbH & Co. Duetschland KGInventor: Uwe Reiher
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Patent number: 5725606Abstract: Dye mixtures comprising at least one dye of formula ##STR1## together with at least one dye of formula ##STR2## 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, C.sub.2 -C.sub.4 -alkanoylamino, halogen or sulfo,R.sub.3 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkanoylamino, halogen or sulfo, andY is C.sub.1 -C.sub.4 alkyl or phenyl or naphthyl, each of which is unsubstituted or substituted byC.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkanoylamino, halogen or sulfo, which dye mixtures contain at least 10% by weight of one or more than one dye of formula (1), based on the total amount of the dyes of formulae (1) and (2), dye nitrogen-containing or hydroxyl group-containing fiber materials with good properties.Type: GrantFiled: April 22, 1996Date of Patent: March 10, 1998Assignee: Ciba Specialty Chemicals CorporationInventor: Guido Jordine
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Patent number: 5630851Abstract: A process for dyeing or printing polyamide material by the trichromatic technique using a dye mixture which contains least two yellow- or orange-dyeing dyes of formula (1) ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen, and X is hydrogen or C.sub.1 -C.sub.4 alkyl; together with at least one red-dyeing dye of formulae (2) and (3) ##STR2## wherein R.sub.2 is C.sub.1 -C.sub.6 alkyl, phenyl or cyclohexyl and R.sub.3 is C.sub.1 -C.sub.6 alkyl, or wherein R.sub.2 and R.sub.3, together with the linking nitrogen atom, form an azepinyl ring, and R.sub.4 is hydrogen, C.sub.2 -C.sub.4 alkanoylamino or halogen; and together with at least one of the blue-dyeing dyes of formulae (4) and (5) ##STR3## wherein R.sub.5 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.6 is C.sub.1 -C.sub.4 alkyl or amino, R.sub.7 is hydrogen or methyl, and R.sub.8 is a C.sub.2-4 hydroxyalkylsulfamoyl radical, is disclosed.Type: GrantFiled: March 1, 1996Date of Patent: May 20, 1997Assignee: Ciba-Geigy CorporationInventors: Guido Jordine, Jean-Marie Adam
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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: 5607502Abstract: A process has been found for dyeing and printing pater, wood, plastic or metal, in which dyestuffs which, in the form of the free acid, correspond to the formula (I) ##STR1## wherein A denotes a phenol radical which is optionally substituted by alkyl or cycloalkyl andn represents 0 or 1,are employed.Type: GrantFiled: October 19, 1995Date of Patent: March 4, 1997Assignee: Bayer AktiengesellschaftInventors: Karin Hassenruck, Peter Wild, Martin Michna
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Patent number: 5456727Abstract: The invention is a dye composition containing two or more dyes of the vinyl sulfone type which can be used in combination to dye polyamide substrates. Preferably the dye compositions of the invention contain at least three dyes of different primary colors.Type: GrantFiled: May 24, 1994Date of Patent: October 10, 1995Assignee: Hoechst Celanese CorporationInventors: Walter Heimling, Mark Helle, Kerry Proulx, Leslie McIntosh, Philomen DeCroos
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Patent number: 5356445Abstract: The invention relates to a process for dyeing natural or synthetic polyamide fiber material from an aqueous liquor, in the presence of a levelling assistant and in the presence or absence of an alkali metal fluorosilicate or ammonium fluorosilicate, which process comprises the use of a mixture of the dyes of formulae (1), (2) and (3) or a mixture of the dyes of formulae (4) and (5), or a mixture which contains the dye of formula (6) together with at least one dye of formulae (7), (8) and (9), which dyes of fomaulae (1) to (9) are as defined in claim 1.The inventive process is suitable for dyeing natural or synthetic polyamide fiber material to give dyeings of fiber and surface levelness having good fastness properties.Type: GrantFiled: September 24, 1993Date of Patent: October 18, 1994Assignee: Ciba-Geigy CorporationInventors: Christian De Meulemeester, Patrick Runser
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Patent number: 5242467Abstract: A reactive dye mixture which comprises, as dye components, from 10 to 57% by weight of C.I. Reactive Orange 16 and from 90 to 43% by weight of C.I. Reactive Orange 7.Type: GrantFiled: August 28, 1992Date of Patent: September 7, 1993Assignee: Hoechst Mitsubishi Kasei Co., Ltd.Inventors: Yuji Yamada, Mitsuhiro Suzuki, Kensuke Suzuki
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Patent number: 5234467Abstract: The invention relates to a dye mixture comprising at least one dye of the formula ##STR1## in which R.sub.1 and R.sub.2, independently of one another, are hydrogen or substituted or unsubstituted C.sub.1 -C.sub.8 alkyl or phenyl, R.sub.3 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.8 alkyl, C.sub.5 -C.sub.7 cycloalkyl or phenyl, R.sub.4 is hydrogen or a radical of the formula ##STR2## R.sub.5 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.8 alkyl or phenyl, and benzene rings I and II may be further substituted, together with at least one dye of the formulae (2) to (6) given in the description.The dye mixtures are suitable for the dyeing or printing of natural and synthetic polyamide fibre materials, in particular in combination with other dyes.Type: GrantFiled: July 14, 1992Date of Patent: August 10, 1993Assignee: Ciba-Geigy CorporationInventor: Jurgen Schaetzer
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Patent number: 5131919Abstract: The invention relates to a dye mixture containing a dye of the formula ##STR1## and a dye of the formula ##STR2## where R is cyclohexyl or phenyl, which may each be substituted by C.sub.1 -C.sub.4 alkyl, acetylamino, N-C.sub.1 -C.sub.4 alkylacetylamino, benzoylamino, ureido or by phenylsulfonylamino or phenylsulfonyloxy which may be substituted in the phenyl ring by C.sub.1 -C.sub.4 alkyl.Said dye mixture is suitable for dyeing and printing natural or synthetic polyamide materials, in particular in combination with other dyes and in particular from short liquors. The mixture is notable for generally good properties, in particular good dyeing properties and good solubility.Type: GrantFiled: April 18, 1991Date of Patent: July 21, 1992Assignee: Ciba-Geigy CorporationInventor: Dieter Mausezahl
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Patent number: 5096460Abstract: The invention relates to a dye mixture containing a dye of the formula ##STR1## in which R.sub.1 is methyl or ethyl and at least one dye of the formulae (2) and (3) ##STR2## in which D is substituted or unsubstituted phenyl, thiophenyl or benzothiazolyl, R.sub.2 is C.sub.1 -C.sub.8 alkyl, R.sub.3 is substituted or unsubstituted C.sub.1 -C.sub.8 alkyl, and R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl, and ##STR3## in which R.sub.5 is C.sub.1 -C.sub.4 alkyl. The dye mixture is distinguished by generally good properties, in particular by good exhaustion.Type: GrantFiled: November 19, 1990Date of Patent: March 17, 1992Assignee: Ciba-Geigy CorporationInventor: Dieter Mausezahl
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Patent number: 5094665Abstract: The invention relates to a dye mixture containing a dye of the formula ##STR1## in which R.sub.1 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halogen, C.sub.2-4 alkanoylamino or an unsubstituted or substituted arylsulfonyl, aryloxy or arylcarbonyl radical, R.sub.2 is hydrogen, halogen, an unsubstituted or substituted alkyl, aryloxy or aryloxysulfonyl radical or a radical of the formula ##STR2## R.sub.3 is unsubstituted or substituted alkyl or aryl radical, R.sub.4 is hydrogen or alkyl and R.sub.5 and R.sub.6 independently of one another are hydrogen or an unsubstituted or substituted alkyl, cycloalkyl or aryl radical, and at least one dye of the formula (2) to (5) ##STR3## in which the benzene rings I, II and III can be substituted, ##STR4## in which the benzene rings IV, V and VI can be substituted and R is hydrogen or arylsulfonyl, ##STR5## in which B.sub.1, B.sub.2 and E.sub.1 are hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or C.sub.2-4 hydroxyalkoxy and X is straight-chain or branched C.sub.Type: GrantFiled: October 18, 1990Date of Patent: March 10, 1992Assignee: Ciba-Geigy CorporationInventor: Dieter Mausezahl
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Patent number: 5092906Abstract: The invention relates to a dye mixture containing a dye of the formula ##STR1## in which R.sub.1 is methyl or ethyl and at least one dye of the formulae (2) to (4) ##STR2## in which R.sub.2 is halogen, benzoylamino which is unsubstituted or substituted in the phenyl ring by halogen, 1-azacycloheptane-N-sulfonyl or ##STR3## in which R.sub.5 is C.sub.1 -C.sub.8 alkyl or phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, and R.sub.6 is hydrogen, or R.sub.5 and R.sub.6 are C.sub.1 -C.sub.8 alkyl, R.sub.3 is hydrogen, halogen or C.sub.1 -C.sub.8 alkyl, and R.sub.4 is hydrogen or halogen, ##STR4## in which D is substituted or unsubstituted phenyl, thiophenyl or benzothiazolyl, R.sub.7 is C.sub.1 -C.sub.8 alkyl, R.sub.8 is substituted or unsubstituted C.sub.1 -C.sub.8 alkyl, and R.sub.9 is hydrogen or C.sub.1 -C.sub.4 alkyl, and ##STR5## in which R.sub.10 is C.sub.1 -C.sub.4 alkyl. The dye mixture is extinguished by generally good properties, in particular by good exhaustion.Type: GrantFiled: November 19, 1990Date of Patent: March 3, 1992Assignee: Ciba-Geigy CorporationInventor: Dieter Mausezahl
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Patent number: 5092905Abstract: Dye mixtures comprising(i) as a yellow component, at least one compound of the formula ##STR1## or a salt thereof, wherein R.sub.1 is hydrogen, C.sub.1-4 alkoxy, C.sub.1-4 alkyl or C.sub.1-4 alkyl monosubstituted by halo,R.sub.2 is C.sub.1-4 alkyl or --COR.sub.6,wherein R.sub.6 is C.sub.1-6 alkyl, C.sub.1-6 alkoxy or --NR.sub.7 R.sub.8,wherein each of R.sub.7 and R.sub.8 is independently hydrogen, C.sub.1-6 -alkyl or C.sub.2-6 alkyl mono-substituted by hydroxy,R.sub.4 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or --NR.sub.3 R.sub.9,R.sub.5 is c.sub.1-4 alkyl or C.sub.2-6 alkyl monosubstituted by hydroxy,R.sub.10 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or --NR.sub.3 R.sub.9, andR.sub.11 is hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, whereineach R.sub.3 is independently hydrogen or C.sub.1-4 alkyl, andeach R.sub.9 is independently (C.sub.1-6 alkyl)carbonyl or (C.sub.Type: GrantFiled: October 4, 1990Date of Patent: March 3, 1992Assignee: Sandoz Ltd.Inventor: Jacky Dore
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Patent number: 5090964Abstract: The invention relates to a dye mixture containing a dye of the formula ##STR1## in which R.sub.1 is methyl or ethyl and at least one dye of the formula ##STR2## in which R.sub.2 is substituted or unsubstituted C.sub.1 -C.sub.8 alkyl is halogen, benzoylamino which unsubstituted or substituted in the phenyl ring by halogen, or 1-azacycloheptane-N-sulfonyl or ##STR3## in which R.sub.5 is C.sub.1 14 C.sub.8 alkyl or phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, and R.sub.6 is hydrogen or C.sub.1 -C.sub.8 alkyl, R.sub.3 is hydrogen, halogen or C.sub.1 -C.sub.8 alkyl, and R.sub.4 is hydrogen or halogen. The dye mixture is distinguished by generally good properties, in particular by good exhaustion.Type: GrantFiled: November 19, 1990Date of Patent: February 25, 1992Assignee: Ciba-Geigy CorporationInventor: Dieter Mausezahl
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Patent number: 5045084Abstract: A process for the trichromatic dyeing or printing of natural and synthetic polyamide fibre materials, which comprises using at least one red dye of the formula ##STR1## in which D,R.sub.1,R.sub.2,R.sub.3,R.sub.4 and n are as defined in claim 1, together with at least one yellow or orange dye of the formula ##STR2## in which B.sub.1,B.sub.2,E.sub.1 and X are as defined in claim 1, or ##STR3## in which Z.sub.1,Z.sub.2 and Z.sub.3 are as defined in claim 1, or mixtures of dyes of the formulae (2) and (3), or a yellow dye of the formula ##STR4## in which W.sub.1,W.sub.2,W.sub.3 and W.sub.4 are as defined in claim 1, or mixtures of dyes of the formulae (2),(3) and (4) and at least one blue dye of the formula ##STR5## in which one Y and Z.sub.4 are as defined in claim 1 are used. The process according to the invention is suitable for dying natural or synthetic polyamide materials from aqueous liquor or for printing with printing pastes; and in particular for dyeing from short liquors.Type: GrantFiled: October 18, 1990Date of Patent: September 3, 1991Assignee: Ciba-Geigy CorporationInventor: Harald Walter
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Patent number: 5007941Abstract: There is disclosed a process for dyeing leather by the exhaust process, which comprises treating leather with an aqueous liquor which contains a formulation comprising an anionic dye and a pigment. The leather dyeings obtained by this process have good allround fastness properties.Type: GrantFiled: December 21, 1989Date of Patent: April 16, 1991Assignee: Ciba-Geigy CorporationInventors: Bruno Martinelli, Markus Ghezzi, Gunter Streicher
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Patent number: 4954133Abstract: Compounds of the formula ##STR1## wherein each A, independently, is a ##STR2## wherein R.sub.1 is hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,R.sub.2 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, --NHCONH.sub.2 or --NHCOC.sub.1-4 alkyl,R.sub.3 is hydrogen or methoxy, andm is 0, 1 or 2,each B, independently, is a radical of a diazo or coupling component, and a and each b, independently, are 0 or 1,and metal complexes thereof, which compounds or complexes are in free acid or salt form, and mixtures thereof with a compound of the formula ##STR3## or a metal complex thereof, wherein A and b are as defined above and D is a radical of a diazo or coupling component of the benzene or 1-naphthalene series are useful for dyeing and printing hydroxy group- or nitrogen-containing organic substrates, especially cellulose fibre-containing textiles (e.g., cotton), paper and leather.Type: GrantFiled: February 12, 1986Date of Patent: September 4, 1990Assignee: Sandoz Ltd.Inventor: Max Oppliger
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Patent number: 4944768Abstract: There are disclosed solid dye formulations which comprise at least one anionic wool dye and optional additional components as well as a mixture of an anionic dispersant and an amphoteric surfactant. Such formulations are distinguished in particular by improved solubility in water.Type: GrantFiled: February 13, 1989Date of Patent: July 31, 1990Assignee: Ciba-Geigy CorporationInventors: Paolo Balliello, Otto Schilling, Beat Bruttel
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Patent number: 4880431Abstract: A monoazo compound of the following formula, ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are independently hydrogen or alkyl, R.sub.4 is alkyl or carboxy, A is ##STR2## in which R.sub.5 is hydrogen, methyl, methoxy, ethoxy, sulfo or carboxy, X is hydrogen or sulfo, n is 0 or 1, and the asterisked linkage bonds to the azo group, B.sub.1 and B.sub.2 are independently phenylene or naphthylene, W is hydrogen, carbamoyl, sulfoalkyl, cyano, sulfo, chloro or bromo, and Y.sub.1 and Y.sub.2 are independently --CH.dbd.CH.sub.2, --CH.sub.2 CH.sub.2 OSO.sub.3 H or the like, which is useful for dyeing hydroxy group- or carbonamide group-containing materials in a deep yellow color excellent in various fastness properties such as light fastness, perspiration-light fastness and chlorine fastness.Type: GrantFiled: December 8, 1987Date of Patent: November 14, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Kazufumi Yokogawa, Naoki Harada, Takashi Omura
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Patent number: 4859207Abstract: A process for dyeing textile planar fabrics made from natural or synthetic polyamides with anionic dyes by(a) locally applying a resist agent by itself or in conjunction with an anionic dye of fluorescent whitening agent,(b) subjecting the textiles to a heat treatment, and(c) carrying out ground dyeing with a dye liquor that contains a further anionic dye,which process comprises using, as resist agent, a melamine compound of formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are each independently phenyl or naphthyl, each of which may be substituted by halogen, hydroxy, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, Z is an acid water-solubilizing group, and m is 1 to 6.Type: GrantFiled: July 19, 1988Date of Patent: August 22, 1989Assignee: Ciba-Geigy CorporationInventors: Thys Bouwknegt, Heinz Abel
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Patent number: 4826505Abstract: A monoazo pyridone compound of the following formula, ##STR1## wherein X is a member selected from hydrogen, halogeno, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, aralkoxycarbonyl, alkylsulfonyl, arylsulfonyl, carbamoyl, sulfamoyl or cyano, and R is alkyl, alkenyl, cycloalkyl, phenyl or anilino, with the provisos that X is a member selected from those defined above except for hydrogen, chloro, methyl and methoxy when R is ethyl, and X is a member selected from those defined above except for alkyl when R is iso-butyl, which is stable under dyeing conditions, and useful for dyeing hydrophobic fiber materials to give dyed products of a deep, fast and brilliant color of greenish yellow to orange.Type: GrantFiled: February 8, 1988Date of Patent: May 2, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Masao Nishikuri, Kiyoyasu Hashimoto, Hideo Hattori
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Patent number: 4780106Abstract: Metal-free compounds of the formula ##STR1## 1:1 and 1:2 metal complexes thereof, and acid addition salts of metal-free compounds of said formula and 1:1 and 1:2 metal complexes thereof, whereinB is hydrogen; C.sub.1-4 alkyl; C.sub.1-4 alkyl monosubstituted by C.sub.1-4 alkoxy; C.sub.2-4 alkyl substituted by hydroxy; C.sub.5-6 cycloalkyl; C.sub.5-6 cycloalkyl substituted by 1 to 3 C.sub.1-4 alkyl groups; 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.4 --N(R.sub.7).sub.2 ; --A.sub.4 --N.sup..sym. (R.sub.8).sub.2 R.sub.9 A.sup..crclbar. or --N(R.sub.7).sub.2,R is hydrogen; C.sub.1-4 alkyl; C.sub.5-6 cycloalkyl; C.sub.5-6 cycloalkyl substituted by 1 or 2 C.sub.Type: GrantFiled: June 10, 1987Date of Patent: October 25, 1988Assignee: Sandoz Ltd.Inventors: Helmut Moser, Manfred Greve, Reinhard Pedrazzi, Roland Wald
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Patent number: 4746323Abstract: This invention is directed to mixtures of water-soluble, fiber reactive yellow dyestuffs which exhibit superior build-up and color properties over those properties obtained with the individual components of the mixtures. The dyestuffs disclosed herein have the following general formula in their free acid form: ##STR1## wherein R is lower alkyl, lower alkoxy or hydrogen and wherein X is --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --Z wherein Z is --OH, --Cl, --Br, --OSO.sub.3 H, --SSO.sub.3 H, OPO.sub.3 H.sub.2 or --N(R.sub.1).sub.2, and wherein R.sub.1 is lower alkyl or hydrogen.Type: GrantFiled: August 24, 1987Date of Patent: May 24, 1988Assignee: Hoechst Celanese CorporationInventors: Thomas S. Phillips, Anthony J. Corso
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Patent number: 4699624Abstract: This invention is directed to mixtures of water-soluble, fiber reactive yellow dyestuffs which exhibit superior build-up and color properties over those properties obtained with the individual components of the mixtures. The dyestuffs disclosed herein have the following general formula in their free acid form: ##STR1## wherein R is lower alkyl, lower alkoxy or hydrogen and wherein X is --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --Z wherein Z is --OH, --Cl, --Br, --OSO.sub.3 H, --SSO.sub.3 H, OPO.sub.3 H.sub.2 or --N(R.sub.1).sub.2, and wherein R.sub.1 is lower alkyl or hydrogen.Type: GrantFiled: April 7, 1986Date of Patent: October 13, 1987Assignee: Hoechst Celanese CorporationInventors: Thomas S. Phillips, Anthony J. Corso
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Patent number: 4685934Abstract: Monoazo compounds of formula ##STR1## wherein R.sub.1 is a coupling component radical,R.sub.1 is C.sub.1-6 alkyl; C.sub.1-6 alkyl substituted by 1 or 2 substituents selected from chloro, cyano, hydroxy, C.sub.1-4 alkoxy, phenyl and phenyl substituted by 1 or 2 substituents selected from chloro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, carboxy, sulfo, sulfamoyl and acetamido; C.sub.5-7 cycloalkyl; C.sub.5-7 cycloalkyl substituted by 1 to 3 C.sub.1-4 alkyl groups; phenyl; phenyl substituted by 1 to 3 substituents selected from chloro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, acetamido (maximum of 1), carboxy (maximum of 1), sulfo (maximum of 1) and --SO.sub.2 NR.sub.7 R.sub.8 (maximum of 1); 1- or 2-naphthyl or 1- or 2-naphthyl substituted by sulfo,whereineach of R.sub.7 and R.sub.8 is independently hydrogen; C.sub.1-4 alkyl; C.sub.1-4 alkyl monosubstituted by hydroxy or phenyl; cyclohexyl; phenyl or phenyl monosubstituted by chloro, methyl or methoxy, or--NR.sub.7 R.sub.Type: GrantFiled: July 12, 1985Date of Patent: August 11, 1987Assignee: Sandoz Ltd.Inventors: Francois Benguerel, Roland Mislin
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Patent number: 4678611Abstract: Dyestuff intermediates of the formula ##STR1## wherein R.sub.1 represents hydrogen, an alkyl radical of 1 to 8 carbon atoms or a phenyl radical, R.sub.2 represents hydrogen or an acyl radical and Z represents hydrogen or a sulfo group, and the use thereof for the manufacture of azo dyes of the formula ##STR2## wherein D represents the radical of a coupling component, R.sub.1 represents hydrogen, an alkyl radical of 1 to 8 carbon atoms or a phenyl radical, and R.sub.2 represents hydrogen or an acyl radical, or of azo dyes of the formula ##STR3## wherein K is the radical of a coupling component, Z represents hydrogen or the sulfo group, and R.sub.2 represents hydrogen or an acyl radical.Type: GrantFiled: January 17, 1986Date of Patent: July 7, 1987Assignee: Ciba-Geigy CorporationInventor: Rudolf Hurter
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Patent number: 4654045Abstract: The present invention is a process for the preparation of concentrated anionic red dye solutions which are storage stable. The process allows manufacture of a solution of a dye having the formula: ##STR1## wherein R.sub.1 is --SO.sub.2 N(CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3).sub.2, --SO.sub.2 N(C.sub.6 H.sub.5)(CH.sub.2 CH.sub.3), --SO.sub.2 N(CH.sub.3)(C.sub.6 H.sub.11), or --CF.sub.3 ;R.sub.2 is --H, --Cl or ##STR2## and R.sub.3 is lower alkyl M is ##STR3## wherein R.sub.4 and R.sub.5 are --H or --CH.sub.3 independently andm+n+q.ltoreq.9, but >0,by reacting a dye having the structure: ##STR4## wherein R.sub.1 is --SO.sub.2 N(CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3).sub.2, --SO.sub.2 N(C.sub.6 H.sub.5)(CH.sub.2 CH.sub.3), --SO.sub.2 N(CH.sub.3)(C.sub.6 H.sub.11), or --CF.sub.3 ;R.sub.2 is --H, --Cl or ##STR5## wherein R.sub.3 is lower alkyl, andX is NH(R.sub.6).sub.3,wherein R.sub.Type: GrantFiled: January 30, 1986Date of Patent: March 31, 1987Assignee: Crompton & Knowles CorporationInventor: Jay E. Rowe
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Patent number: 4652269Abstract: Process for the continuous trichromatic dyeing of synthetic polyamide materials which comprises using at least one blue-dyeing fibre-reactive sulfo-containing anthraquinone dye together with at least one red-dyeing sulfo-containing azo dye and at least one yellow- or orange-dyeing sulfo-containing azo dye.The process according to the invention is suitable for the continuous dyeing of synthetic polyamide materials from aqueous liquors, producing level dyeings having good fastness properties, in particular good ozone fastness.Type: GrantFiled: April 30, 1986Date of Patent: March 24, 1987Assignee: Ciba-Geigy CorporationInventors: James B. Bowles, Marshall White, Jr., Alois Puntener, Jean-Marie Adam, Peter Loew
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Patent number: 4622045Abstract: The invention provides a process for dyeing a textile substrate comprising wool fibres, which process comprises bringing the substrate into contact with an aqueous dyebath containing an acid dyestuff or a mixture of acid dyestuffs having(a) a build-up power on wool of from 90 to 98% at pH 4.5; together with(b) a migrating ability on wool of from 25 to 40%, at pH 4.5;(a) and (b) being determined under specific conditions, in the presence of a levelling agent which is the alkoxylation product of an amine substituted by a fatty saturated or unsaturated residue, the aqueous dyebath containing a mixture of acid dyestuffs when the substrate is a wool/synthetic polyamide fibre blend.These dyestuffs give level, fast and reproducible dyeings of a high quality.Type: GrantFiled: September 28, 1984Date of Patent: November 11, 1986Assignee: Sandoz Ltd.Inventors: Josef Frauenknecht, Karl Zeller
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Patent number: 4579561Abstract: A trichromatic dye system for the dyeing of synthetic polyamide fibers, the system including an acid red dye component, an acid blue dye component, and an acid yellow dye component, each of the dye components being compatible from a performance standpoint.Type: GrantFiled: January 9, 1985Date of Patent: April 1, 1986Assignee: Crompton and Knowles CorporationInventors: Jay E. Rowe, James F. Feeman
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Patent number: 4563192Abstract: The invention relates to a process for dyeing synthetic polyamide fibre material with dyes or dye mixtures in the presence of a mixture of dyeing assistants, which comprises using for the dyeing of these materials an aqueous liquor which contains at least one anionic dye which, under the defined dyeing conditions, has a degree of exhaustion of at least 95% at 1/1 standard depth of shade, and a dyeing assistant mixture containing an anionic compound, a quaternary compound and a non-ionic compound, and wherein the liquor contains an alkali metal salt and an organic acid, and finishing the dyeing at pH 5-7, preferably pH 5.5-6, and at a temperature of 95.degree. to 130.degree. C.The process according to the invention is suitable for dyeing synthetic polyamide materials, producing level dyeings having good fastness properties with all types of dye or mixtures of dyes of identical or different types.Type: GrantFiled: September 14, 1984Date of Patent: January 7, 1986Assignee: Ciba-Geigy CorporationInventors: Heinz Salathe, Hermann Flensberg, Harry Schaetzer
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Patent number: 4560386Abstract: Disclosed is a method for dyeing sueded wool- or fur-bearing skins tone-in-tone in a single bath and in one step. The dyeing is carried out with reactive dyestuffs bearing at least one reactive group selected from acryloylimino, halogenoacryloylimino and .beta.-halogenopropionylimino, in the presence of non-ionic or anionically modified polyalkoxylated surfactants.Type: GrantFiled: March 16, 1984Date of Patent: December 24, 1985Assignee: Sandoz Ltd.Inventors: Tony A. Hopkins, Rudolf Seitz
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Patent number: 4553976Abstract: The invention describes a process for dyeing or printing natural or synthetic polyamide fibre material by a rapid fixation method, which comprises the use of dyes or mixtures of dyes of the formulae as defined in the description in a continuous dyeing method or printing method, and fixing the dyes or prints by steaming for less than 3 minutes such that at least 95% fixation of the dyes is achieved. The process is particularly suitable for combination dyeing and polyamide carpet printing, and produces level dyeings and prints having excellent fastness properties.Type: GrantFiled: January 12, 1984Date of Patent: November 19, 1985Assignee: Ciba-Geigy CorporationInventors: Helmut Raisin, Bernard C. Teutelink
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Patent number: 4537598Abstract: A process for dyeing or printing natural and synthetic polyamide material by the trichromatic technique, which comprises the use of a red dye of the formula (1) defined in the specification, or a mixture of the red dye of the formula (1) with a red dye of the formula (2) together with at least one yellow or orange dye of the formula (3), or a mixture of at least one yellow or orange dye of the formula (3) with a yellow dye of the formula (4) and at least one blue dye of the formula (5). The process of the invention is suitable for dyeing natural or synthetic polyamide material from an aqueous liquor or for printing with printing pastes. It is particularly suitable for dyeing from short liquors.Type: GrantFiled: May 24, 1984Date of Patent: August 27, 1985Assignee: Ciba-Geigy CorporationInventors: Harry Schaetzer, Helmut Raisin, Dieter Mausezahl
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Patent number: 4496364Abstract: A process for dyeing a voluminous flat form polyamide substrate with anionic dyestuffs according to the cold pad-batch method, which process comprises the step of selecting the initial pH of the dyeing liquor within a range depending on the affinity of the substrate for anionic dyestuffs and the molecular weight of the anionic dyestuffs so as to give a substantial linear exhaustion of the dyeing liquor, the dyeing liquor being free from a thickening, swelling or foaming agent.Type: GrantFiled: April 25, 1983Date of Patent: January 29, 1985Assignee: Sandoz Ltd.Inventor: Hans-Peter Stakelbeck
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Patent number: 4469485Abstract: Disclosed are the 1:2 chromium complex of the formula ##STR1## and the alkali metal salts thereof which are useful for the coloration of oxide layers produced on aluminum and alloys thereof and for dyeing natural and synthetic polyamides.Type: GrantFiled: August 22, 1983Date of Patent: September 4, 1984Assignee: Sandoz Ltd.Inventor: Hans Grossmann