Formazan Containing (i.e., Hnh-n=ch-n=nh, Wherein Substitution May Be Made For Hydrogen Only) Patents (Class 534/618)
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Patent number: 10093816Abstract: The present invention is related to a novel high fixation ink composition for digital textile printing, which comprises: (A) at least one reactive dye compound with two reactive groups in an amount of 1% to 50% by weight; (B) an organic buffer in an amount of 0.05% to 10% by weight; (C) a humectant in an amount of 10% to 50% by weight; and (D) a solvent in remaining amount. When the aforesaid ink composition is applied in digital textile printing, fixation rate of dye on fabrics is high.Type: GrantFiled: April 26, 2016Date of Patent: October 9, 2018Assignee: EVERLIGHT CHEMICAL INDUSTRIAL CORPORATIONInventors: Hsiao-San Chen, Chuan-Hsi Lee, Chien-Yu Chen, Tz-Yi Wu, Hsuan Yang
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Patent number: 9732467Abstract: An ink jet textile printing method includes recording by applying an ink composition containing a dye to a front surface of a fabric by an ink jet method and applying a liquid penetrant to the front surface or a rear surface of the fabric before or after the recording. The liquid penetrant includes a nitrogen compound having a boiling point of 230 to 260° C. and an alkyl polyol having a boiling point of 230 to 260° C. and does not substantially include alkyl polyols having a boiling point higher than 260° C.Type: GrantFiled: January 26, 2016Date of Patent: August 15, 2017Assignee: Seiko Epson CorporationInventor: Hidehiko Komatsu
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Patent number: 9045421Abstract: Method and reagent for converting a carboxylic acid to a positively charge amide are described. The method and reagent facilitate positive ion mass spectral analysis of carboxylic acids. The method includes reacting a carboxylic acid with a compound having formula I: wherein A and B are aromatic rings, ring A includes a quaternized nitrogen and has n additional ring atoms, each additional ring atom optionally substituted with an RA group, and n is an integer from 4 to 10, and ring B includes a carbon atom and has m additional ring atoms, each additional ring atom optionally substituted with an RB group, and m is an integer from 4 to 10. The compound includes at least one RA or RB group, and the at least one RA and RB group is -L-N(Z)H; and X? is a counterion.Type: GrantFiled: April 1, 2011Date of Patent: June 2, 2015Assignee: University of WashingtonInventors: Michael H. Gelb, Frantisek Turecek, James Bollinger
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Patent number: 7604669Abstract: Dye mixtures, comprising at least one dye of formula and at least one dye from the group of formulae wherein B1, B2 and B3 are each independently of the others an organic bridging member, Q1 is C1-C4alkyl, halogen or a radical —SO2-Z, Q2 and Q3 are each independently of the other C1-C4alkoxy, Q4 is C1-C4alkoxy, C1-C4alkyl, halogen or sulfo Q5 is C1-C4alkoxy, C1-C4alkyl, C1-C4alkanoylamino, ureido, halogen or sulfo, R1, R2, R3, R4, R5, R6, R7, R8 and R9 are each independently of the others hydrogen or unsubstituted or substituted C1-C4alkyl, k and q are each independently of the other the number 0 or 1, n and p are each independently of the other the number 0, 1 or 2, m is the number 0, 1, 2 or 3, t is the number 1, 2 or 3, X1, X2, X3, X4, X5 and X6 are each independently of the others halogen, and T1, T2 and T3 are each independently of the others a non-fiber-reactive substituent or a fiber-reactive radical of formula wherein (R10)0-2 denotes from 0 to 2 identical or different substituents frType: GrantFiled: November 6, 2006Date of Patent: October 20, 2009Assignee: Huntsman International LLCInventors: Jean-Marie Sire, Athanassios Tzikas, Georg Roentgen
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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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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: 7087730Abstract: Reactive dyes of formula (I), wherein A is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan or dioxazine chromophore, Q1, and Q2 are each independently of the other hydrogen or unsubstituted or substituted C1–C4alkyl, (Q3)n denotes n substituents selected from the group C1–C4alkyl, C1–C4alkoxy, halogen and sulfo, X is halogen, 3-carboxypyridin-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, Y is vinyl or a radical —CH2—CH2—U and U is a group removable under alkaline conditions, k is a number 2, 3, 4, 5 or 6, m is a number 0 or 1, and n is a number 0, 1 or 2, with the proviso that when A denotes a monoazo chromophore it is not directly linked to the triazinyl radical through a hydroxynaType: GrantFiled: July 15, 2003Date of Patent: August 8, 2006Assignee: Ciba Specialty Chemicals CorporationInventors: Athanassios Tzikas, Bernhard Müller, Georg Roentgen
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Patent number: 7057024Abstract: Black-dyeing aqueous inks comprising 20 to 95% by weight of at least one dye (A), together with 5 to 80% by weight of at least one dye chosen from the group consisting of (B) and (C), based on the total weight of the dyes (A), (B) and (C) in the ink, and 1 to 40% by weight of a water-miscible organic solvent, based on the total weight of the ink, the dye (A) containing, as the colouring part of the molecule, one or more radicals of the formula (I), (II), (III) or (IV) the dye (B) containing, as the coloring part of the molecule, one or more mono- or disazo radicals containing sulfo groups or one or more radicals of the formula (V), (VI), (VII) or (VIII) and the dye (C) containing, as the coloring part of the molecule, one or more mono- or disazo radicals containing sulfo groups or one or more radicals of the abovementioned formula (V), (VI), (VII) or (VIII) and one or more radicals of the abovementioned formula (I), (II), (III) or (IV), in which (G)0-2 is 0 to 2 identical or different substituenType: GrantFiled: January 30, 2002Date of Patent: June 6, 2006Assignee: Ciba Specialty Chemicals CorporationInventors: Urs Lehmann, Athanassios Tzikas, Marcel Frick
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Patent number: 7015314Abstract: This invention relates to novel fibre-reactive formazan dyes of the formula (I): where the symbols are each as defined in claim 1, their preparation, their use for dyeing and printing hydroxyl-containing or nitrogenous organic substrates and substrates dyed or printed with these compounds.Type: GrantFiled: July 29, 2002Date of Patent: March 21, 2006Assignee: Clariant Finance (BVI) LimitedInventor: Markus Gisler
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Patent number: 6864361Abstract: The present invention refers to dyestuffs of the formula I wherein each of R1, R2, R3, R4 and R5, independently, is H or an optionally substituted alkyl group; each of X1 and X2, independently, is a labile atom or group; each of x and y, independently, is 0 or 1 and at least one of x and y is 1; each of a and b is 2 to 5 and when each of x and y is 1, a>b; and z is 0, 1, 2, 3 or 4; and wherein the variables D1 and D2 are defined as given in claim 1, processes for their preparation and their use for dyeing and printing hydroxy- and/or carboxamido-containing fiber materials.Type: GrantFiled: July 1, 2003Date of Patent: March 8, 2005Assignee: DyStar Textilfarben GmbH & Co. Deutschland KGInventors: Warren James Ebenezer, Werner Russ
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Publication number: 20040167321Abstract: This invention relates to novel fibre-reactive formazan dyes of the formula (I): 1Type: ApplicationFiled: January 22, 2004Publication date: August 26, 2004Inventor: Markus Gisler
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Publication number: 20030060608Abstract: Disclosed are compositions for printing recording materials, especially textile fibre materials, paper and papery substrates and plastic films and plastic transparencies by the inkjet printing process, includingType: ApplicationFiled: September 20, 2002Publication date: March 27, 2003Inventors: Ludwig Hasemann, Reinhard Pedrazzi, Josef Geisenberger, Josef Ritter, Hans-Tobias Macholdt, Andreas Wuzik
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Patent number: 6444794Abstract: Disclosed are water-soluble dyes, such as azo dyes, metal complex dyes, anthraquinone, phthalocyanine and formazan dyes which, optionally via a bridge member, possess a fiber-reactive group of the vinyl sulfone series and further contain a 4-cyanamido-1,3,5-triazin-6-ylamino radical which is 2-substituted by a group of the general formula (2) where Rz is hydrogen, lower alkyl optionally substituted by alkyl, hydroxyl, cyano, lower alkoxy, carboxyl, sulfamoyl, sulfo or sulfato or an optionally substituted phenyl radical, or is a cyclohexyl radical or an optionally substituted phenyl radical, W is an alkyl radical which is substituted by a reactive group and may be interrupted by a hetero atom, A is zero or 1 and B is 1 or 2, subject to the proviso that the sum of (A+B) is 2.Type: GrantFiled: May 22, 2000Date of Patent: September 3, 2002Assignee: DyStar Textilfarben GmbH & Co. Deutschland KGInventors: Jörg Dannheim, Stefan Ehrenberg
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Patent number: 6407220Abstract: The present invention provides reactive formazan dyestuffs of the general formula (I), Wherein A, B, D, Me, Q, R, and Z are defined in this document. The dyes according to the invention are distinguished by high fixation and a very good build-up. They are distinguished also by a low substantivity and a high exhaustion, and they have fiber-reactive properties and are very highly suitable for dyeing and printing of materials containing either cellulose fibers.Type: GrantFiled: December 14, 2001Date of Patent: June 18, 2002Assignee: Everlight USA, Inc.Inventors: Huei Ching Huang, Wen-Jang Chen
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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: 6353094Abstract: Dyes of the formula in which Me, R1, X1, A, u and q are as defined in the specification are particularly suitable for dyeing cotton and produce dyeings with good all-round properties.Type: GrantFiled: March 15, 2000Date of Patent: March 5, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Athanassios Tzikas, Herbert Klier
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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: 6307034Abstract: Reactive dyes of formula (1) wherein R1, R2, R3 and R4 are each independently of the others hydrogen or unsubstituted or substituted C1-C4alkyl, X1 and X2 are halogen, B is a C2-C12alkylene radical which may be interrupted by 1, 2 or 3 —O— members and is unsubstituted or substituted by hydroxy, A is a formazan radical of formula (2) or (3) D is a radical of formula (4) or (5) wherein m, n and R5 are as defined in the claims are suitable especially for dyeing or printing hydroxy-group-containing or nitrogen-containing fiber materials. Olive-green dyeings are obtained having good fastness properties and a high tinctorial yield.Type: GrantFiled: September 25, 2000Date of Patent: October 23, 2001Assignee: Ciba Specialty Chemicals CorporationInventor: Hans Reichert
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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: 6197941Abstract: Reactive dyes of the formula I where a is 1 or 2, b is 0 or 1, Y is vinyl or a radical of the formula C2H4Q, where Q is an alkali-detachable group, Het is the radical of a 5- or 6-membered aromatic hetero-cyclic ring having from 1 to 3 hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, W is either in case 1) the radical of a coupling component, of a monoazo dye or additionally, when b=0, of a disazo dye, which may each bear further fiber-reactive groups, or in case 2) the radical of a chromophore which optionally has further fiber-reactive groups and is derived from an optionally metallized mono- or disazo dye, a triphendioxazine, an anthraquinone, a metallized formazan or a metallized phthalocyanine, and L1 and L2 are each a bridge member, are useful for dyeing or printing hydroxyl-containing or nitrogenous substrates.Type: GrantFiled: March 29, 1999Date of Patent: March 6, 2001Assignee: BASF AktiengesellschaftInventors: Andrea Zamponi, Manfred Patsch, Helmut Hagen, Bernd-Peter Walther
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Patent number: 6086640Abstract: For dyeing (printing, for example) cellulose fibers with a reactive dye, a blue compound is greatly desired, the blue compound being capable of generating a product dyed in blue at excellent dyeing reproducibility and with good light fastness and superior fastness against chlorine water, involving less staining of white area. The invention relates to a formazan compound in a free acid form as represented by the following formula I, a dyeing method of cellulose fibers using the same and a final dyed product prepared by the method, characterized in that the compound, the method and the product are suitable so as to overcome the problem.Formula I ##STR1## (wherein R represents hydrogen, sulfo group, hydroxyl group, halogen, a C1-C4 alkyl group, a C1-C4 alkoxyl group or carboxyl group; and M represents copper or nickel.Type: GrantFiled: August 9, 1999Date of Patent: July 11, 2000Assignee: Nippon Kayaku Kabushiki KaishaInventors: Toru Tabei, Eiichi Ogawa, Shin-ichi Namba
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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: 6046311Abstract: Dyes containing a 5,6-difluoropyrimidin-4-yl radical as fiber-reactive group are useful for dyeing hydroxy- and/or carboxamido-containing material, including fiber material, for example cellulose fibers, wool and polyamide.Type: GrantFiled: March 19, 1998Date of Patent: April 4, 2000Assignee: DyStar Textilfarben GmbH & Co. Deutschland KGInventors: Wilfried Hansmann, Hermann Henk, Stefan Ehrenberg, Wolfram Reddig
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Patent number: 6025478Abstract: Reactive dyestuff of the formula ##STR1## wherein D is a radical of a monaozo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone or nitroaryl organic dyestuff,a process for their preparation and their use for dyeing fiber materials containing OH groups and NH groups have been found.Type: GrantFiled: February 27, 1998Date of Patent: February 15, 2000Assignee: Bayer AGInventors: Klaus Kunde, Karl-Josef Herd
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Patent number: 5936072Abstract: A description is given of reactive dyes of formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other hydrogen, sulfo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen,X is fluoro or chloro, andY is a --CHT--CH.sub.2 T or --CT.dbd.CH.sub.2 group, and T is bromo or chloro. The reactive dyes of formula (1) are particularly suitable for dyeing or printing cellulosic fiber materials.Type: GrantFiled: March 12, 1998Date of Patent: August 10, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Athanassios Tzikas, Herbert Klier
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Patent number: 5936073Abstract: The present invention provides the reactive formazan dyestuffs of the following formula (I), ##STR1## wherein m, Y, R, X.sub.1, X.sub.2, and M are defined in this document. These kinds of dyestuffs have deep-dyeing ability, and they are suitable for dyeing and printing of materials containing either cellulose fibers, such as cotton, synthetic cotton, hemp, and synthetic hemp.Type: GrantFiled: December 4, 1998Date of Patent: August 10, 1999Assignee: Everlight USA, Inc.Inventors: Duncan Adrian Sidney Phillips, John Anthony Taylor, Wen-Jang Chen
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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: 5858026Abstract: The invention relates to dicyclic metal complex formazan dye derivatives and processes for producing compositions and for using them in dyeing processes.Type: GrantFiled: December 5, 1996Date of Patent: January 12, 1999Assignee: Kyung-In Synthetic CorporationInventors: Dong Gil Kim, Sung Yong Cho
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Patent number: 5837827Abstract: Compounds of the formula ##STR1## in which the variables have the meaning given in the claims, which are suitable as fibre-reactive dyes for dyeing or printing widely varying fibre materials are described.Type: GrantFiled: November 12, 1996Date of Patent: November 17, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Hans Reichert, Herbert Klier
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Patent number: 5834601Abstract: Dyes of the formula (1) indicated and defined below, containing at least one sulfo group, which can be used for dyeing hydroxy and/or carboxamido-containing material, especially fiber material, for example cellulosic fiber materials, wool and synthetic polyamide. ##STR1## in which F is the radical of a dye molecule, n is the number 1 or 2, R.sup.A is hydrogen or substituted or unsubstituted lower alkyl, R.sup.B is hydrogen, unsubstituted or substituted lower alkyl or unsubstituted or substituted phenyl, X is halogen, R is hydrogen, lower alkyl, lower alkoxy halogen or sulfo, and G at the benzene ring forms the radical of a heterocycle which includes at least one carbonylamido group whose N atom can be substituted.Type: GrantFiled: October 17, 1997Date of Patent: November 10, 1998Assignee: Dystar Textilfarben GmbH & Co. Deutschland KGInventors: Stefan Ehrenberg, Christian Schumacher
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Monoazotriaziayl group-containing fiber reactive dyes, processes for their preparation and their use
Patent number: 5760194Abstract: Reactive dyes of the formula ##STR1## in which D is a radical of the formula ##STR2## are particularly suitable for dyeing or printing natural or synthetic polyamide fibre materials.Type: GrantFiled: November 19, 1996Date of Patent: June 2, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Urs Lehmann, Marcel Frick -
Patent number: 5717078Abstract: Reactive dyes of the formula ##STR1## in which 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,X.sub.1 and X.sub.2 are halogen,B.sub.1 is an aromatic or aliphatic bridge member, or the radical of the formula --N(R.sub.2)--B.sub.1 --N(R.sub.3)-- is a piperazine radical,A.sub.1 is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan or dioxazine chromophore and,A.sub.2 is a radical of the formula ##STR2## in which D.sub.1 is substituted or unsubstituted phenyl or naphthyl,R.sub.5 and R.sub.6 independently of one another are hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl, alk is substituted or unsubstituted C.sub.2 -C.sub.6 alkylene andZ is vinyl or a radical --CH.sub.2 --CH.sub.2 --U.sub.1, and U.sub.1 is a leaving group, andthe radicals A.sub.1 and A.sub.Type: GrantFiled: August 22, 1996Date of Patent: February 10, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Athanassios Tzikas, Peter Aeschlimann
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Patent number: 5717077Abstract: A phthalocyanine monoazo compound which is represented by the following formula (I): ##STR1## wherein Pc represents a phthalocyanine group; M represents nickel, cobalt or copper;R.sub.1 represents a hydrogen atom or a lower alkyl group;R.sub.2 and R.sub.3 represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a sulfo group;R.sub.4 represents a hydrogen or a lower alkyl group;A represents a group containing a triazine group or a pyrazole group and/or --SO.sub.2 X wherein X represents --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 Y and Y represents a group splittable by the action of an alkali;p is a number of 0-2; q is a number of 1-3; r is a number of 1-2; p+q+r is 4 or lessor which is a salt of the compound of formula (I).Type: GrantFiled: December 11, 1995Date of Patent: February 10, 1998Assignee: Sumitomo Chemical Company, LimitedInventors: Toshiyuki Araki, Takemi Tokieda, Shin-ichi Yabushita, Yasuyoshi Ueda, Bunzi Tsukise
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Patent number: 5684138Abstract: Reactive dyes of the formula ##STR1## in which 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,B is an aliphatic bridge member,Y.sub.1 and Y.sub.2 independently of one another are halogen or carboxypyridinium,A.sub.1 is the radical of an anthraquinone, phthalocyanine, dioxazine, formazan or disazo dye or a radical of the formulae (2a) to (2h) defined in claim 1 andA.sub.2 is as defined above for A.sub.1 or is a radical of the formulae (2i) to (2m),where A.sub.1 and A.sub.2 have different meanings to one another, are particularly suitable for dyeing or printing fibre materials containing hydroxyl groups or containing nitrogen. Dyeings having good fastness properties coupled with a high tinctorial yield are obtained.Type: GrantFiled: May 29, 1996Date of Patent: November 4, 1997Assignee: Ciba Specialty Chemicals CorporationInventors: Herbert Klier, Bernhard Muller, Edmond Ruhlmann, Athanassios Tzikas
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Patent number: 5677434Abstract: A family of 1:2 Fe-complexed formazan dyes is described. The dyes unexpectedly afford reddish-violet, violet, blue and black shades on natural and synthetic substrates. Methods for synthesizing the dyes and for dyeing a substrate are described. The dyes represent environmentally friendly alternatives to conventional Cr- and Co-based azo and formazan dyes.Type: GrantFiled: May 31, 1996Date of Patent: October 14, 1997Assignee: North Carolina State UniversityInventors: Harold S. Freeman, Jolanta Sokolowska-Gajda, Abraham Reife
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Patent number: 5599911Abstract: Reactive dyes of the formula ##STR1## in which the variables have the meanings stated in the claims, are described. The dyes according to the invention are particularly suitable for dyeing cellulosic fibre materials and give dyeings with good fastness properties and a high color yield.Type: GrantFiled: August 25, 1994Date of Patent: February 4, 1997Assignee: Ciba-Geigy CorporationInventors: Rolf Deitz, Bernhard M uller, Athanassios Tzikas
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Patent number: 5591834Abstract: Reactive dyestuffs of the formula ##STR1## in which Z is a cyano-free pyrimidine 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: December 22, 1994Date of Patent: January 7, 1997Assignee: Bayer AktiengesellschaftInventors: Konrad Bootz, Karl-Josef Herd
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Patent number: 5565553Abstract: Reactive dyes of the formula ##STR1## where A, K and Z are each as defined in the claims, are especially useful for dyeing or printing cellulosic fiber materials, producing dyeings and prints having good fastness properties in a high yield.Type: GrantFiled: January 11, 1996Date of Patent: October 15, 1996Assignee: Ciba-Geigy CorporationInventors: Rolf Deitz, Paul Herzig, Athanassios Tzikas
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Patent number: 5563248Abstract: 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 23, 1995Date of Patent: October 8, 1996Assignee: Hoechst Celanese CorporationInventors: Walter Helmling, Philomen DeCroos
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Patent number: 5552532Abstract: Reactive dyes of the formula ##STR1## in which 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,B is an aliphatic bridge member,Y.sub.1 and Y.sub.2 independently of one another are halogen or carboxypyridinium,A.sub.1 is the radical of an anthraquinone, phthalocyanine, dioxazine, formazan or disazo dye or a radical of the formulae (2a) to (2h) defined in claim 1 andA.sub.2 is as defined above for A.sub.1 or is a radical of the formulae (2i) to (2m),where A.sub.1 and A.sub.2 have different meanings to one another, are particularly suitable for dyeing or printing fibre materials containing hydroxyl groups or containing nitrogen. Dyeings having good fastness properties coupled with a high tinctorial yield are obtained.Type: GrantFiled: May 13, 1994Date of Patent: September 3, 1996Assignee: Ciba-Geigy CorporationInventors: Herbert Klier, Bernhard M uller, Edmond Ruhlmann, Athanassios Tzikas
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Patent number: 5548071Abstract: The invention relates to compounds of the formula ##STR1## where the variables are each as defined in the claims. The compounds are suitable for use as dyes, in particular for dyeing and printing cellulose-containing fibre materials and produce dyeings and prints having good allround fastness properties.Type: GrantFiled: May 13, 1994Date of Patent: August 20, 1996Assignee: Ciba-Geigy CorporationInventors: Rolf Deitz, Athanassios Tzikas, Paul Herzig
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Patent number: 5536876Abstract: Fiber-reactive formazan dyes are prepared by diazotizing a protectively formylated hydroxyphenylenediamine, coupling with a hydrazone compound, metallizing, eliminating the protective group, and reacting with a halotriazine and optionally thereafter with an amine or a hydroxy compound via novel aminophenol intermediates.Type: GrantFiled: October 31, 1994Date of Patent: July 16, 1996Assignee: BASF AktiengesellschaftInventors: Claus Marschner, Manfred Patsch
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Patent number: 5491221Abstract: Fibre-reactive formazan compounds, salts thereof or free acid forms thereof according to formula (I) ##STR1## in which R.sub.1 is hydrogen or --COOH, each of R.sub.2 and R.sub.4 is independently hydrogen, --COOH, --SO.sub.3 H, --NHCOCH.sub.3, --NHCOCHY.sub.2 --CH.sub.2 Y.sub.1, --NHCOCY.sub.2 .dbd.CH.sub.2 or --NHCOCH.sub.2 Y.sub.1,R.sub.3 is hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, --COOH or --SO.sub.3 H,Y.sub.1 is chlorine, bromine, --OSO.sub.3 H or --SSO.sub.3 H,Y.sub.2 is hydrogen, chlorine or bromine, andZ is ##STR2## The compounds are particularly useful in dyeing or printing hydroxy-group containing or nitrogen-containing organic substrates, including leather, fiber materials, and textiles.Type: GrantFiled: May 20, 1994Date of Patent: February 13, 1996Assignee: Sandoz Ltd.Inventors: Markus Gisler, Roland Wald
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Patent number: 5488100Abstract: There are described formazan dyes of the formula ##STR1## where m and n are each 1 or 2,Kat.sup..sym. is the equivalent of a cation,Me is copper or nickel,X is oxygen or a radical of the formula CO--O or SO.sub.2 --O,Y is vinyl or a radical of the formula C.sub.2 H.sub.4 --Q, wherein Q is a group that is detachable under alkaline reaction conditions,E is a fiber-reactive radical,the rings A and B may be substituted and benzofused, andthe ring C may be substituted,the use thereof for dyeing or printing hydroxyl- or nitrogen-containing organic substrates, novel aminophenols and a process for preparing same.Type: GrantFiled: March 22, 1995Date of Patent: January 30, 1996Assignee: BASF AktiengesellschaftInventors: Claus Marschner, Manfred Patsch
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Patent number: 5484899Abstract: The invention relates to compounds of the formula ##STR1## in which the variables are as defined in the claims. The compounds are suitable as dyes, in particular for dyeing and printing cellulosic fibre materials, and produce dyeings and prints with good all-round fastness properties.Type: GrantFiled: May 3, 1994Date of Patent: January 16, 1996Assignee: Ciba-Geigy CorporationInventors: Rolf Deitz, Athanassios Tzikas
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Patent number: 5463031Abstract: Reactive dyestuffs of the formula ##STR1## in which the substituents have the meanings given in the description are highly suitable for the dyeing and printing of cellulose materials and nitrogen-containing materials.They produce dyeings and prints having good wet and light fastness properties.Type: GrantFiled: April 12, 1994Date of Patent: October 31, 1995Assignee: Bayer AktiengesellschaftInventors: Horst Jager, Frank-Michael Stohr, Karl K. Schundehutte
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Patent number: 5451666Abstract: A water-soluble dye having a reactive group of the Formula (1): ##STR1## wherein: R.sup.1 is H or optionally substituted alkyl;R.sup.2 is H or C.sub.1-4 -alkyl;L is a divalent organic spacer group; andV is vinyl or a group convertible to vinyl on treatment with aqueous alkali.The reactive dyes of the present invention are useful for coloring natural and artificial textile materials containing amino or hydroxyl groups.Type: GrantFiled: June 9, 1993Date of Patent: September 19, 1995Assignee: Zeneca LimitedInventor: Kenneth Anderton
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Patent number: 5451665Abstract: The invention relates to dye mixtures which contain dyes of the formulae ##STR1## and to dyes of the formula ##STR2## in which A.sub.1, A.sub.2, A.sub.3, B, B.sub.1, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, Z.sub.1, Z,.sub.2, X.sub.1, X.sub.2 and X.sub.3 are as defined in claim 1.The dyes and dye mixtures are distinguished by generally good properties and produce dyeings and prints having good wet and light fastness properties.Type: GrantFiled: April 15, 1993Date of Patent: September 19, 1995Assignee: Ciba-Geigy CorporationInventor: Athanassios Tzikas
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Patent number: 5420255Abstract: A process for the continuous reaction of halogenopyrimidines with amines, a halogenopyrimidine and an aqueous amine solution or suspension being passed into a reactor and the reaction product being subsequently conducted away, is described, characterized in that the starting materials are introduced into the reactor simultaneously and continuously with intensive mixing.Type: GrantFiled: February 22, 1994Date of Patent: May 30, 1995Assignee: Bayer AktiengesellschaftInventors: Siegbert Arnold, Hans-Georg Frosch, Manfred Hoppe, Wolfgang Mullers, Richard Sommer