The Hetero Ring And Benzene Ring, To Which An Azo Group Is Bonded Directly, Bonded Directly To The Same Nitrogen Patents (Class 534/638)
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Patent number: 9193870Abstract: Reactive dyes of formula (1) wherein Q1 and Q2 are each independently of the other hydrogen or unsubstituted or substituted C1-C4alkyl, A is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan or dioxazine chromophore, X is halogen, 3- or 4-carboxypyridin-1-yl, or 3- or 4-carbamoylpyridin-1-yl, Y is vinyl or a radical —CH2—CH2—U and U is a group removable under alkaline conditions, and q is the number 1 or 2, are suitable for dyeing and printing cellulosic or amide-group-containing fiber materials.Type: GrantFiled: May 24, 2013Date of Patent: November 24, 2015Assignee: Huntsman International LLCInventors: Georg Roentgen, Jean-Christophe Graciet, Rainer Hildebrand, Laszlo Fekete, Marie Schmidlin, Hubert Jean-Luc Christnacher
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Publication number: 20150096131Abstract: Reactive dyes of formula (1) wherein Q1 and Q2 are each independently of the other hydrogen or unsubstituted or substituted C1-C4alkyl, A is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan or dioxazine chromophore, X is halogen, 3- or 4-carboxypyridin-1-yl, or 3- or 4-carbamoylpyridin-1-yl, Y is vinyl or a radical —CH2—CH2—U and U is a group removable under alkaline conditions, and q is the number 1 or 2, are suitable for dyeing and printing cellulosic or amide-group-containing fibre materials.Type: ApplicationFiled: May 24, 2013Publication date: April 9, 2015Inventors: Georg Roentgen, Jean-Christophe Graciet, Rainer Hildebrand, Laszlo Fekete, Marie Schmidlin, Hubert Jean-Luc Christnacher
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Patent number: 7632316Abstract: The present invention relates to dyes of the general formula (1) where M and X are each as defined in claim 1, dye mixtures comprising one or more of the dyes of the general formula (1) and also one or more further fiber-reactive dyes, processes for their preparation, their use and printing inks comprising same.Type: GrantFiled: May 24, 2006Date of Patent: December 15, 2009Assignee: DyStar Textilfarben GmbH & Co. Deutschland KGInventors: Stefan Meier, Uwe Reiher, Werner Hubert Russ, Günther Schwaiger
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Patent number: 7439340Abstract: A reactive dyestuff containing an alkylthio-s-triazinyl reactive group of the following formula (I) is disclosed, wherein A, X, Y, Z, R, Q, and a are defined the same as the specification. It is suitable for exhaust dyeing, cold batch-up dyeing and continuous dyeing materials that contain hydroxyl group or nitrogen group fibers.Type: GrantFiled: February 15, 2007Date of Patent: October 21, 2008Assignee: Everlight USA, Inc.Inventors: Wen-Jang Chen, Hsien-Chung Shia, Duncan Adrian Sidney Phillips, John Anthony Taylor
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Publication number: 20080207881Abstract: A reactive dyestuff containing an alkylthio-s-triazinyl reactive group of the following formula (I) is disclosed, wherein A, X, Y, Z, R, Q, and a are defined the same as the specification. It is suitable for exhaust dyeing, cold batch-up dyeing and continuous dyeing materials that contain hydroxyl group or nitrogen group fibers.Type: ApplicationFiled: April 30, 2008Publication date: August 28, 2008Applicant: Everlight USA, Inc.Inventors: Wen-Jang Chen, Hsien-Chung Shia, Duncan Adrian Sidney Phillips, John Anthony Taylor
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Publication number: 20080189880Abstract: The present invention relates to dyes of the general formula (1) where M and X are each as defined in claim 1, dye mixtures comprising one or more of the dyes of the general formula (1) and also one or more further fiber-reactive dyes, processes for their preparation, their use and printing inks comprising same.Type: ApplicationFiled: May 24, 2006Publication date: August 14, 2008Applicant: DyStar Textilfarben GmbH & Co. Deutschland KGInventors: Stefan Meier, Uwe Reiher, Werner Hubert Russ, Gunther Schwaiger
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Patent number: 7326777Abstract: A fiber reactive dyestuff of the following formula (I) wherein the definition of D, R, R1, R2, X and Z have the same meaning as given in the specification. The fiber reactive dyestuff of the present invention is suitable for dyeing and printing on cellulose fiber or fiber materials containing cellulose. Dyed material with various excellent properties in dyed color can be obtained, showing especially outstanding performance in the property of wash fastness, build-up and chlorine fastness.Type: GrantFiled: October 6, 2005Date of Patent: February 5, 2008Assignee: Everlight USA, Inc.Inventors: Wen-Jang Chen, Hong-Chang Huang
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Patent number: 7129336Abstract: The present invention relates to reactive dyes of the general formula (1) where Y is a heterocyclic reactive group of the general formula (2) or (3) where X1 to X5 are each as defined in claim 1, processes for their preparation and their use for dyeing and printing hydroxyl- and/or carboxamido-containing materials.Type: GrantFiled: January 10, 2005Date of Patent: October 31, 2006Assignee: DyStar Textilfarben GmbH & Co. Deutschland KGInventors: Stefan Ehrenberg, Jörg Wörner, Tracy Livesey
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Patent number: 7122667Abstract: Reactive dyes of formula (1) wherein Q1, Q2, Q3 and Q4 are each independently of the others hydrogen or unsubstituted or substituted C1–C4alkyl, A is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan or dioxazine chromophore, D is the radical of a diazo component, of the benzene or naphthalene series, X is halogen, 3-carboxpyridin-1-yl, 3-carbamoylpyridin-1-yl, hydroxy, C1–C4alkoxy unsubstituted or substituted in the alkyl moiety, phenoxy unsubstituted or substituted in the phenyl moiety, C1–C4alkylthio unsubstituted or substituted in the alkyl moiety, unsubstituted or substituted amino, or an N-heterocycle which may or may not contain further hetero atoms, and Y is vinyl or a radical —CH2—CH2—U and U is a group removable under alkaline conditions, are suitable for dyeing cellulosic or amide-group-containing fibre materials.Type: GrantFiled: October 29, 2002Date of Patent: October 17, 2006Assignee: Ciba Specialty Chemicals CorporationInventors: Athanassios Tzikas, Bernhard Müller
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Patent number: 7109313Abstract: The present invention relates to dyes of the general formula (I) where X1 is a radical —CH2CH2Z or —CH?CH2, Z being analkali-eliminable group, X2 is alkyl, alkoxy, halogen, COOM or SO3M, X3 is a heterocyclic reactive group of the general formula (IIa) or (IIb) ?or a reactive group of the formula (IIc), (IId) or (IIe) the stated variables being as defined in claim 1, to processes for preparing them and to their use for dyeing and printing hydroxyl-containing and/or carboxamido-containing material.Type: GrantFiled: March 18, 2003Date of Patent: September 19, 2006Assignee: DyStar Textilfarben GmbH & Co. Deutschland KGInventors: Stefan Meier, Werner Russ, Stefan Ehrenberg
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Patent number: 7091328Abstract: According to the invention there are provided fiber-reactive dyestuffs which are compounds of the formula (I) wherein the substituents are defined as in claim 1, a process making the same and their use in dyeing or printing hydroxy-group-containing organic substrates.Type: GrantFiled: April 15, 2002Date of Patent: August 15, 2006Assignee: Clariant Finance (BVI) LimitedInventors: Roland Wald, Markus Gisler
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Patent number: 7038024Abstract: Reactive dyes containing at least one structural unit of formula (I), wherein Y is vinyl or a radical —CH2—CH2—U and U is a group removable under alkaline conditions, are suitable for dyeing cellulosic or amide-group-containing fiber materials.Type: GrantFiled: October 4, 2002Date of Patent: May 2, 2006Assignee: Ciba Specialty Chemicals CorporationInventors: Athanassios Tzikas, Bernhard Müller
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Patent number: 6949631Abstract: The present invention relates to reactive dyes of the general formula (1) where X1, X2, R, M, m and n are each as defined in claim 1, processes for their preparation and also their use for dyeing and printing hydroxyl- and/or carboxamido-containing materials.Type: GrantFiled: November 28, 2002Date of Patent: September 27, 2005Assignee: DyStar Textilfarbon GmbH & Co. Deutschland KGInventors: Stefan Meier, Werner Russ, Jörg Wörner
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Patent number: 6930179Abstract: Method for the trichromatic dyeing or printing of synthetic polyamide fiber material, wherein at least one red reactive dye of formula is used together with at least one of the yellow or orange reactive dyes of formulae and at least one blue reactive dye of formula in which formulae the variables are as defined in claim 1, which method is distinguished by a uniform color build-up and a very good combinability.Type: GrantFiled: May 17, 2004Date of Patent: August 16, 2005Assignee: Ciba Specialty Chemicals CorporationInventors: Jürgen Schmiedl, Klaus Koch, Wolfgang Mundle, Franz Grüner
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Patent number: 6900294Abstract: The present invention relates to reactive dyes of the general formula (1) where Y is a heterocyclic reactive group of the general formula (2) or (3) where X1 to X5 are each as defined in claim 1, their preparation and their use for dyeing and printing hydroxyl- and/or carboxamido-containing materials.Type: GrantFiled: August 11, 2001Date of Patent: May 31, 2005Assignee: DyStar Textilfarben GmbH & Co. Deutschland KGInventors: Stefan Meier, Werner Russ, Jörg Wörner
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Patent number: 6815536Abstract: A monoazo reactive red dyestuff of the formula (I), wherein the R1, R2, R3, X, D, Z and n are as defined in the description. These kinds of dyestuffs are suitable for dyeing and printing of materials containing either cellulose fibers, such as cotton, artificial cotton, linen, and artificial linen, or synthetic polyamide, such as wool, silk, and nylon etc., as well as on mixed or cross-linked cellulose fibers and other fibers. Dyed materials with excellent properties can be obtained, showing especially outstanding performance in of wash-off, level-dyeing, light fastness and perspiration-light fastness.Type: GrantFiled: October 17, 2002Date of Patent: November 9, 2004Assignee: Everlight USA, Inc.Inventors: Huei-Chin Huang, Chia-Huei Yu
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Patent number: 6809187Abstract: Reactive copper, cobalt or chromium complex compounds of the general formula (1) where R1-R5, M, Me, W1, X, k, l and m are each as defined in claim 1, processes for their preparation and their use for dyeing or printing textile fiber materials.Type: GrantFiled: April 10, 2003Date of Patent: October 26, 2004Assignee: Oystar Textil Farben GmbH & Co.Inventors: Stefan Ehrenberg, Klaus Kunde
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Patent number: 6790943Abstract: A reactive dye compound comprising: (a) at least one chromophore moiety; (b) at least one SO2C2H4 group which is attached to the chromophore moiety either directly via the sulphur atom of the SO2C2H4 group or via a linking group L; characterized in that at least one SO2C2H4 group is substituted on its terminal carbon atom with at least one Y group wherein Y is derived from a hydrated aldehyde, a hydrated ketone, a hydrated alpha-hydroxy ketone or the hydrated form of formic acid, and linked via one of its oxygen atoms to the terminal carbon of the SO2C2H4 group thereby forming a hemiacetal.Type: GrantFiled: March 27, 2002Date of Patent: September 14, 2004Assignee: North Carolina State UniversityInventors: Peter Jeffrey Broadbent, David Malcolm Lewis, Gilles Yves Marie Fernand Genain, Wei Dong He, Taher Iqbal Yousaf
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Patent number: 6723834Abstract: A reactive dye compound comprising: (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; characterized in that at least one nitrogen-containing heterocycle is substituted with at least one Y group wherein Y is derived from a hydrated aldehyde, a hydrated ketone, a hydrated alpha-hydroxy ketone, or the hydrated form of formic acid and linked via one of its oxygen atoms to the nitrogen-containing heterocycle thereby forming a hemiacetal.Type: GrantFiled: March 27, 2002Date of Patent: April 20, 2004Assignee: North Carolina State UniversityInventors: Peter Jeffrey Broadbent, Dong Wei He, David Malcolm Lewis, Gilles Yves Marie Fernand Ganain, Taher Iqbal Yousaf
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Patent number: 6713613Abstract: A reactive dye compound comprising: (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 oxy- or thio-carbonyl derivative wherein the oxy- or thio-carbonyl derivative is selected from Y wherein Y is —A(CO)R* wherein A is selected from O or S and wherein R* is an organic residue which comprises at least one nucleophilic group, and salts thereof.Type: GrantFiled: November 8, 2001Date of Patent: March 30, 2004Assignee: North Carolina State UniversityInventors: David Malcolm Lewis, Wei Dong He, Taher Iqbal Yousaf, Gilles Yves Marie Fernand Genain
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Patent number: 6624291Abstract: Monoazo dyestuffs of the formula (1) wherein Y is vinyl or is ethyl which is substituted in the &bgr;-position by a substituent which can be eliminated by the action of an alkali, forming the vinyl group; M, X, are groups customary to dyestuffs, R1, R2 is hydrogen methyl, methoxy or sulfo; Q is cyanamido or is a group of the formula (a) or (b): A, B, D are hydrogen, optionally substituted C1-C6 alkyl or phenyl, or is alternately a group of the formula (a) or (b) wherein (a) is a cyclic ring system having a tertiary nitrogen of (b) is a cyclic having a quarternary nitrogen; n is 0 if Q is a group of the formula (a) and n is 1 if Q is a group of formula (b); W— is a halogenide or the equivalent of a divalent anionic group; The invention further relates to the method for preparing the dyestuff and use for dyeing.Type: GrantFiled: July 24, 2001Date of Patent: September 23, 2003Assignee: DyStar Textilfarben GmbH & Co. Deutschland KGInventor: Ronald Pedemonte
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Patent number: 6552175Abstract: Reactive dyes of formula wherein R1 is halogen, C1-C4alkyl, C1-C4alkoxy, C2-C4alkanoylamino, &agr;,&bgr;-dihalopropionylamino or &agr;-haloacryloylamino, X is halogen, n is the number 0, 1 or 2, and V is a radical of formula wherein (R2)l denotes l identical or different substituents selected from the group halogen, hydroxy, nitro, sulfo, C1-C4alkyl and C1-C4alkoxy, Y is &agr;,&bgr;-dihalopropionylamino, &agr;-haloacryloylamino or a radical —CONH—(CH2)2-3—SO2—Z and Z is vinyl or a radical —CH2CH2—U and U is a group removable under alkaline conditions, m is the number 0 or 1, and l is the number 0, 1, 2 or 3, with the proviso that R1 is not &agr;,&bgr;-dihalopropionylamino or &agr;-haloacryloylamino when V is a radical of formula (2) wherein Y is &agr;,&bgr;-dihalopropionylamino or &agr;-haloacryloylamino, are suitable for the dyeing or printing of cellulosic fiber materials or natural or synthetic polyamide fiber materials, witType: GrantFiled: March 29, 2002Date of Patent: April 22, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: Jürgen Schmiedl, Carlos Moyano
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Patent number: 6518409Abstract: Reactive dyes of formula wherein R1 and R2 are each independently of the other hydrogen or unsubstituted or substituted C1-C4alkyl, A is C2-C8alkylene interrupted by oxygen, X is halogen, and Y is a fiber-reactive radical of formula (2) —SO2—Z (2) wherein Z is vinyl or a radical —CH2—CH2—U and U is a group removable under alkaline conditions, are suitable especially for dyeing cotton and yield dyeings having good allround properties.Type: GrantFiled: March 19, 2001Date of Patent: February 11, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: Athanassios Tzikas, Rolf Deitz, Bruno Cortese
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Patent number: 6410698Abstract: The reactive dyes have the general formula I where n is 0 or 1, m is 0 or 1, Y is vinyl or a radical of the formula C2H4Q, where Q is an alkali-detachable group, L is C2-C6-alkylene with or without interruption by 1 or 2 nonadjacent oxygen atoms or 1 or 2 imino groups or is cyclohexylene, Hal is fluorine or chlorine, R1 is hydrogen or hydroxysulfonylmethyl, R2 is hydrogen or hydroxysulfonylmethyl, and R3 is carboxyl or hydroxysulfonyl and may also be hydrogen when R1 and/or R2 are each hydroxysulfonylmethyl.Type: GrantFiled: September 7, 2000Date of Patent: June 25, 2002Assignee: BASF AktiengesellschaftInventors: Frank Prechtl, Manfred Patsch
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Patent number: 6398822Abstract: Packaged hair coloring composition comprising a stable aqueous hair coloring composition comprising a compound of formula (I): wherein the variables are each as defined in the claims. The packaged hair coloring compositions of the present invention provide improved wash fastness of dye on hair, less color fade over time, improved consumer acceptance in terms of providing a single packaged hair dye composition and improved product stability.Type: GrantFiled: December 18, 2000Date of Patent: June 4, 2002Assignee: The Proctor & Gamble CompanyInventors: Earl David Brock, Heather Holden Harper, Taher Iqbal Yousaf
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Patent number: 6399751Abstract: This application relates to reactive dyes having at least one halobenzene nucleus linked to a chromophoric group via an amino linkage and additionally containing a second reactive group.Type: GrantFiled: July 24, 2000Date of Patent: June 4, 2002Assignee: BASF AktiengesellschaftInventors: Warren James Ebenezer, David Greenwood, Michael Gordon Hutchings, Michael Alan Rabjohns, Andrea Maria Zamponi
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Patent number: 6395885Abstract: The use of lithium as a cation for an anionic dye to enhance the light-fastness of the dye. Also claimed are the lithium salts of certain anionic dyes as defined in the description; mixed lithium/sodium salts of an anionic dye wherein the molar ratio of lithium to sodium is from 1:4 to 99:1 and at least 20 mole % of the total counter ions in the dye are lithium cations; inks containing the dyes; a method of ink jet printing using the inks; a substrate printed with the inks; an ink jet printer cartridge containing the ink and a ink jet printer containing the ink jet printer cartridge.Type: GrantFiled: December 5, 2000Date of Patent: May 28, 2002Assignee: Avecia LimitedInventors: Aidan Joseph Lavery, Janette Watkinson, John Parker Meyers
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Patent number: 6372893Abstract: Claimed are novel azo dyes of the formula (I) where the substituents are each as defined in the claims, their preparation, their use as dyes and as an ingredient of an ink-jet printing ink and also substrates dyed with such compounds.Type: GrantFiled: October 31, 2000Date of Patent: April 16, 2002Assignee: Clariant Finance (BVI) LimitedInventor: Rainer Nusser
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Patent number: 6329514Abstract: A fiber reactive dyestuff of the following formula (I) wherein the definition of D, and Z the same meaning as given in the description. The fiber reactive dyestuff of the present invention is suitable for dyeing and printing on cellulose fiber or fiber materials containing cellulose. Dyed material with various excellent properties in dyed color can be obtained, showing especially outstanding performance in the property of wash fastness.Type: GrantFiled: February 8, 2000Date of Patent: December 11, 2001Assignee: Everlight USA, Inc.Inventors: Huei Ching Huang, Keh Loong Chen, Mao Cheng Hsu, Ta Chung Yin
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Patent number: 6319290Abstract: Compounds of the general formula (I) wherein R1 represents hydrogen or a C1-C4-alkyl group, X represents the radical of aliphatic, cyclic or aromatic diamines and Y represents hydrogen or an alkali metal, and a process for their preparation and their use for dyeing organic substrates, and organic substrates dyed with these compounds.Type: GrantFiled: December 9, 1999Date of Patent: November 20, 2001Assignee: Clariant Finance (BVI) LimitedInventors: Detlef Kalweit, Martin Oberholzer
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Patent number: 6310187Abstract: The present invention relates to a bifunctional red reactive dye and more particularly, to the bifunctional red reactive dye with monochlorotriazine and acetoxyethylsulfone as reactive groups expressed by formula (I), wherein, M is alkaline metal atom, which provides excellent combination of properties in that 1) the introduction of aminophenyl-&bgr;-acetoxyethylsulfone group to the dye may minimize the loss of dye, since its low solubility to water lessens the amount of the remaining solution during filtration, 2) an easier salting-out process requires a smaller amount of salt during the process so that the costs for the treatment of waste water may be significantly reduced, and 3) a better dyeing yield with enhanced substantivity and better brightness in colorType: GrantFiled: April 9, 2001Date of Patent: October 30, 2001Assignee: Korea Research Institute of Chemical TechnologyInventors: Sea Wha Oh, Myeong Nyeo Kang, Seung Rim Shin, Tae Kyung Kim, Mi Kyoung Song
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Patent number: 6281339Abstract: Monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan or dioxazine dyes comprising at least one structural unit of formula (1) wherein Z is C1-C24alkoxy unsubstituted or substituted in the alkyl moiety, or uninterrupted or interrupted in the alkyl moiety by oxygen; phenoxy unsubstituted or substituted in the phenyl ring; C1-C4alkylthio unsubstituted or substituted in the alkyl moiety; phenylthio unsubstituted or substituted in the phenyl ring; amino; N-mono- or N,N-di-C1-C24-alkylamino, unsubstituted or substituted in the alkyl moiety, or uninterrupted or interrupted in the alkyl moiety by oxygen or by a radical —NR1— in which R1 is hydrogen or C1-C4alkyl; C10-C20terpeneamino; C5-C7cycloalkylamino unsubstituted or substituted in the cycloalkyl ring; phenyl- or naphthyl-amino or N—C1-C4alkyl-N-phenyl- or N—C1-C4alkyl-N-naphthyl-amino, each unsubstituted or substituted in the aryl moiety; morpholino; piperazin-1-yl or piperidin-1-yl, and X is hydType: GrantFiled: September 13, 2000Date of Patent: August 28, 2001Assignee: Ciba Specialty Chemicals CorporationInventors: Urs Lehmann, Marcel Frick
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Patent number: 6271355Abstract: Dyes of Formula (1) which are useful for the coloration of e.g. cellulosic materials and leathers. wherein: NiPc is a nickel phthalocyanine radical; r has a value from 1 to 3 inclusive; m has a value from 1 to 3 inclusive; p has a value from 0 to 1 inclusive; R1 is H, alkyl, substituted alkyl, aryl or substituted aryl; R2, R3 and R4 are each independently H, C1-6-alkyl or substituted C1-6-alkyl; A is phenylene, substituted phenylene, C1-6-alkylene or substituted C1-6-alkylene; Q is a labile substituent; B is phenylene, phenylene substituted by 1 or 2 sulpho groups or phenylene substituted by an alkyl or alkoxy group; Z is H or alkyl; and X and Y are each independently H, alkyl, alkoxy, halogen, carboxy or sulpho; provided that r+m+p does not exceed 4.Type: GrantFiled: August 17, 1993Date of Patent: August 7, 2001Assignee: Imperial Chemical Industries PLCInventors: Denis Robert Annesley Ridyard, Andrew Hunter Morris Renfrew
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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: 6200963Abstract: wherein: R1 is a moiety selected from: R2 is CH2CH2CONH2 or CH2CH2OH; R3 and R4 are independent substituents selected from the group including H, —N(CH3)2, or —OCH3; or pharmaceutically acceptable salts thereof.Type: GrantFiled: March 24, 2000Date of Patent: March 13, 2001Assignee: American Home Products CorporationInventors: Jay E. Wrobel, John F. Rogers, Wenling Kao
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Patent number: 6177552Abstract: Described are fiber-reactive water-soluble azo compounds which contain a group of the general formula (2) as diazo component where R21 is hydrogen, methyl, ethyl, methoxy, ethoxy or sulfo, R22 is hydrogen, methyl, ethyl, methoxy, ethoxy or sulfo, R23 is hydrogen, alkyl of 1 to 4 carbon atoms or phenyl, n is 2 or 3 and the group —SO2—Y is a fiber-reactive group of the vinyl sulfone series, and which are capable of dyeing hydroxy- and/or carboxamido-containing material, especially fiber material, such as cellulose fibers, for example cotton, or regenerated cellulose fibers and also wool and synthetic polyamide fibers in high color strength and good fastnesses.Type: GrantFiled: December 28, 1999Date of Patent: January 23, 2001Assignee: DyStarTextilfarben GmbH & Co. Deutschland KGInventors: Uwe Reiher, Ron Pedemonte
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Patent number: 6159250Abstract: Doubled reactive dyes of the general formula I ##STR1## where Chr is a chromophore residue with or without further fiber-reactive groups and derived from a metallized or unmetallized mono- or disazo dye, from a triphendioxazine, from an anthraquinone, from a metallized formazan or from a metallized phthalocyanine,Z.sup.1, Z.sup.2 and Z.sup.3 are each independently of the others hydrogen or substituted or unsubstituted C.sub.1 -C.sub.6 -alkyl,Hal is fluorine or chlorineL.sup.1 and L.sup.2 are each independently of the other C.sub.2 -C.sub.6 -alkylene with or without interruption by 1 or 2 unadjacent oxygen atoms, andA is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.6 -alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted C.sub.2 -C.sub.3 -alkenyl, substituted or unsubstituted C.sub.1 -C.sub.6 -alkoxy, substituted or unsubstituted phenoxy or C.sub.1 -C.sub.6 -alkylamino,and their mixtures are prepared and useful for dyeing or printing hydroxyl-containing or nitrogenous substances.Type: GrantFiled: December 22, 1999Date of Patent: December 12, 2000Assignee: BASF AktiengesellschaftInventor: Manfred Patsch
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Patent number: 6127531Abstract: A dyestuff according to formula (I) ##STR1## or a salt thereof wherein the substituents have the definitions as defined in claim 1.The dyestuffs are useful for dyeing or printing nitrogen-containing or hydroxy-group-containing organic substrates and for the production of printing inks.Type: GrantFiled: May 26, 1999Date of Patent: October 3, 2000Assignee: Clariant Finance (BVI) LimitedInventor: Rainer Nusser
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Patent number: 6124441Abstract: Described are fiber-reactive, water-soluble monoazo compounds which conform to the hereinbelow indicated and defined general formula (1) and which are capable of dyeing hydroxy- and/or carboxamido-containing material, especially fiber material, such as cellulose fibers, for example cotton or regenerated cellulose fibers, and also wool and synthetic polyamide fibers in high color strength and good fastnesses. ##STR1## where M is hydrogen, an alkali metal or some other salt-forming, colorless metal, D is a 2-sulfophenyl radical which may be additionally substituted by alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, sulfo and/or carboxy or is a 1-sulfonaphth-2-yl radical which may be additionally substituted by sulfo and/or carboxy, and the group --SO.sub.2 --Y is a fiber-reactive group of the vinyl sulfone series.Type: GrantFiled: April 13, 1999Date of Patent: September 26, 2000Assignee: DyStar Textilfarben GmbH & Co. Deutschland KGInventors: Stefan Ehrenberg, Karl-Josef Herd
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Patent number: 6114511Abstract: Fiber-reactive, water-soluble monoazo compounds conforming to the hereinbelow indicated and defined general formula (1) are capable of dyeing hydroxyl- and/or carboxamido-containing material, especially fiber material, such as cellulose fibers, for example cotton, or regenerated cellulose fibers and also wool and synthetic polyamide fibers in red shades and in high color strength and good fastnesses. ##STR1## where M is hydrogen, an alkali metal or some other colorless salt-forming metal, R is hydrogen or optionally sulfo-, methoxy-, ethoxy-, hydroxyl-, sulfato-, phosphate-, acetyloxy- or propionyloxy-substituted alkyl of 1 to 4 carbon atoms, R.sup.1 is hydrogen, carboxyl, optionally substituted alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, m is zero or 1, n is zero, 1 or 2 and X is a fiber-reactive radical from the halopyrimidine, dichloroquinoxazoline or fluorotriazinylamino series.Type: GrantFiled: May 24, 1999Date of Patent: September 5, 2000Assignee: Dystar Textilfarben GmbH & Co.Inventor: Jorg Dannheim
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Patent number: 6060591Abstract: The disclosed dyes (which are fiber-reactive and are useful for dyeing materials containing OH and/or carboxamide groups) are compounds of the formula (1)Fb--Z.sub.n (1)in which:Fb is the radical of various classes of dyestuffs, including the formazans, azomethines, phthalocyanines, etc., and particularly sulfo group-containing monoazo or disazo dyes of the formulas (a-1) through (a-5):D.sup.1 --N.dbd.N--K.sup.2 -- (a-1)--D.sup.2 --N.dbd.N--(E--N.dbd.N).sub.v --K.sup.1 (a-2)--D.sup.2 --N.dbd.N--(E--N.dbd.N).sub.v --K.sup.2 -- (a-3)D.sup.1 --N.dbd.N--K.sup.0 --N.dbd.N--D.sup.2 -- (a-4)--D.sup.1 --N.dbd.N--K.sup.0 --N.dbd.N--D.sup.2 -- (a-5)in which in which D.sup.1 is a substituted or unsubstituted phenyl or naphthyl radical, D.sup.2 is the radical of a diazo component and K.sup.1, K.sup.2, and K.sup.0 are various coupling components, and E is a middle component.Type: GrantFiled: December 1, 1997Date of Patent: May 9, 2000Assignee: Dy Star Textilfarben GmbH & Co. Deutschland K.G.Inventors: Wilfried Hansmann, Hermann Henk, Stefan Ehrenberg, Wolfram Reddig
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Patent number: 6042621Abstract: The application is concerned with a compound of the formula (I) ##STR1## and a process for making the same. The compound is useful as fiber-reactive dyestuff in dyeing or printing onto hydroxy- or nitrogen-containing substrates. A printing composition comprising this fiber-reactive dyestuff and a copper phthalocyanine allows to obtain dyeings with less catalytic fading.Type: GrantFiled: August 11, 1998Date of Patent: March 28, 2000Assignee: Clariant Finance (BV) LimitedInventors: Roland Wald, Paul Doswald
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Patent number: 6022384Abstract: The present invention relates to a water-soluble reactive dye of the formula N(Z).sub.3, wherein each Z independently has the formula (III): ##STR1## wherein m, Q, Y and D are defined in the claims. The present invention also relates to a process for coloring a substrate that includes applying to the substrate the water-soluble reactive dye of the above formula at a pH above 7.Type: GrantFiled: February 24, 1999Date of Patent: February 8, 2000Assignee: Zeneca LimitedInventor: John Anthony Taylor
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Patent number: 6022956Abstract: Described are fiber-reactive, water-soluble monoazo compounds conforming to the hereinbelow indicated and defined general formula (1) that are capable of dyeing hydroxyl- and/or carboxamido-containing material, especially fiber material, such as cellulose fibers, for example cotton, or regenerated cellulose fibers and also wool and synthetic polyamide fibers in red shades and in high color strength and good fastnesses. ##STR1## where M is hydrogen or an alkali metal, m is 1, 2 or 3, X is chlorine or fluorine, R.sup.0 is hydrogen or carboxyl, R is alkyl of 1 to 4 carbon atoms which is unsubstituted or substituted by hydroxyl, carboxyl, sulfo, sulfato, phosphate, chlorine, alkanoyloxy of 2 to 5 carbon atoms or alkoxy of 1 to 4 carbon atoms, and R is hydrogen, alkyl of 1 to 4 carbon atoms, which may be substituted, alkoxy of 1 to 4 carbon atoms, which may be substituted, alkanoylamino of 2 to 5 carbon atoms, optionally substituted benzoylamino or halogen, and R.sup.2 is hydrogen, carboxyl or sulfo and the --SO.Type: GrantFiled: May 10, 1999Date of Patent: February 8, 2000Assignee: Dy Star Textilfarben GmbH & Co. Deutschland KGInventors: Jorg Dannheim, Manfred Hoppe
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Patent number: 6020470Abstract: The present invention provides novel water-soluble azo compounds derived from 2-hydroxynaphthalene-3,6-dicarboxylic acid or derivatives thereof and diazonium salts having sulfo group(s). These compounds are useful as raw materials for dyes having excellent dyeing properties and fastness.Type: GrantFiled: March 22, 1999Date of Patent: February 1, 2000Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Masaya Kitayama, Kenji Minami, Masaharu Kittaka
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Patent number: 5962655Abstract: There is provided a monoazo compound which is useful as a reactive dye for dyeing or printing a fiber material in an orange to scarlet color; and intermediate compounds for producing the compound is provided; the monoazo compound being represented by the following formula (1): ##STR1## wherein m represents 0 or 1; R.sup.1 represents a hydrogen atom or a lower alkyl group; D represents a specific diazo component of benzene type having substitution of a fiber reactive group; B.sup.1 represents a direct bond or connecting group; Z.sup.1 represents an alkylcarbonyl group, phenylcarbonyl group or a fiber-reactive group of vinylsulfone, triazine or pirimidine type; a group represented by --NR.sup.1 -- bonds to 6-position or 7-position of a naphthalene ring;and the intermediate compounds being represented by the following formulae (A) or (B): ##STR2## wherein U represents a connecting group such as alkylene and the like, Y represents vinyl or --CH.sub.2 CH.sub.Type: GrantFiled: January 20, 1998Date of Patent: October 5, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Nobutaka Kunimi, Shigeru Sasaki, Kouji Toishi, Atsushi Inoue
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Patent number: 5952476Abstract: A red reactive dyestuff of the formula (I) ##STR1## wherein the substituents have the meaning given in the description. The red reactive dyestuff of the present invention is suitable for dying and printing on cellulose fiber such as cotton, artificial cotton, linen and artificial linen, etc., and polyamide and polyurethane fibers like wool, silk and nylon, etc. It is also suitable for dying and printing on mixed or cross-linking spinning of cellulose fiber or polyamide fiber and polyurethane fiber, polyacrylonitrile fiber and other fiber.Type: GrantFiled: August 21, 1998Date of Patent: September 14, 1999Assignee: Everlight USA, Inc.Inventors: Duncan Adrian Sidney Phillips, Yung-Chien Kao
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Patent number: 5931975Abstract: Dyes of the formula ##STR1## in which A.sub.1 and A.sub.2 independently of one another are the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye,R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently of one another are hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl,Y.sub.1 and Y.sub.2 independently of one another are halogen, carboxypyridinium, substituted or unsubstituted amino or a heterocyclic radical bonded via a nitrogen atom andn is a number from 1 to 7,are particularly suitable for dyeing or printing fiber materials containing hydroxyl groups or nitrogen. Dyeings with good fastness properties are obtained with a high dyeing yield.Type: GrantFiled: October 16, 1997Date of Patent: August 3, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Bernhard Muller, Patric Nowack
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Patent number: 5929217Abstract: Reactive dyes of the formula I ##STR1## where a is 1 or 2,b is 0 or 1,Z.sup.1 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, halogen, nitro, amino, hydroxysulfonyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, carbamoyl or C.sub.1 -C.sub.6 -mono- or dialkylcarbamoyl,A is methylene, carbonyl, sulfonyl or a radical of the formula CH.sub.2 --CO or CH.sub.2 --SO.sub.2,X is a direct linkage or a linker,Y.sup.1 is vinyl or a radical of the formula C.sub.2 H.sub.4 Q where Q is a group which can be eliminated under alkaline conditions,W is in case 1) the radical of a chromophore which may have further reactive groups, or in case 2) the radical of a coupling component to which additionally the radical of a diazo component may be linked via an azo bridge and which may have additional reactive groups, andL.sup.1 and L.sup.2 are each linkers,their intermediates and a process for dyeing or printing substrates having hydroxyl groups or nitrogen atoms using the novel dyes are described.Type: GrantFiled: March 22, 1996Date of Patent: July 27, 1999Assignee: BASF AktiengesellschaftInventors: Manfred Patsch, Hermann Loffler, Claus Marschner
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Patent number: RE37004Abstract: A water-soluble monoazodye having the following formula (I) in its free acid form: ##STR1## wherein X is --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 W wherein W is a leaving group removable by alkali; R.sup.1 is methyl, --NHCONH.sub.2 or --NHCOT.sup.1 wherein T.sup.1 is methyl, ethyl, --CH.sub.2 CH.sub.2 COOH or --CH.dbd.CHCOOH; R.sup.2 is hydrogen, lower alkyl or lower alkoxy; and Z is ##STR2## wherein P is cyano or halogen, each of Q and U which are independent of each other, is halogen, V is halogen or ##STR3## and Y is halogen or a group of the following formula (1) or (2): ##STR4## wherein R.sup.3, A, R.sup.4 and E are as defined in the disclosure and G is as defined above, has a moderate yellow to orange color and is particularly suitable for dyeing cellulose fibers or nitrogen-containing fibers.Type: GrantFiled: August 22, 1997Date of Patent: December 26, 2000Assignee: Dystar Japan Ltd.Inventors: Yousuke Takahashi, Yukihara Shimizu, Toshio Hihara, Kiyoshi Himeno