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: 5310886Abstract: There are disclosed azo compounds conforming to formula (1) shown and defined hereinafter, and the preparation thereof. They have fiber-reactive properties and are used for preparing strong and fast dyeings on hydroxy- and/or carboxamido-containing material, preferably fiber material, such as synthetic polyamide, wool and in particular cellulose fibers. ##STR1## where: M is hydrogen or a salt-forming metal,K.sup.o is a radical of the formula (2A) or (2B) ##STR2## where Z is a radical of the formula (3) ##STR3## where R.sup.o is hydrogen or lower alkyl which may be substituted by certain substituents, G is halogen, methoxy, hydroxy or substituted or unsubstituted anilino, Z.sup.1 is a radical of the formula (3a) or (3b) ##STR4##--alk--SO.sub.2 --Yand wherein A, B, R*, R", Y, a, k, D, E and K are as defined in the specification.Type: GrantFiled: June 25, 1992Date of Patent: May 10, 1994Assignee: Hoechst AktiengesellschaftInventors: Hartmut Springer, Kurt Hussong
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Patent number: 5300633Abstract: Azo compounds of the formula D.sup.o --N.dbd.N--K.sup.o, in which D.sup.o is a radical of the formula (2), (2a) or (2b) ##STR1## in which Y is a substituent which can be eliminated by alkali to form the vinyl group, X is chlorine or bromine and R is hydrogen, lower alkyl, phenyl or halogen, and K.sup.o is the radical of a coupling component or another radical which contains azo groups, K.sup.o containing a group of the formula --N(R.sup.o)--Z, in which R.sup.o is hydrogen or lower alkyl and Z is a radical of the formula ##STR2## in which A is halogen or cyanoamido, R.sup.20 is hydrogen or lower alkyl, and R.sup.21 has one of the meanings given for R.sup.20, or is an optionally methyl-substituted cycloalkylene radical, or is a phenyl radical, or in which R.sup.20 and R.sup.21, together with the nitrogen atom and if appropriate one or two further hetero groups, can form a 5- or 6-membered heterocyclic radical.Type: GrantFiled: May 8, 1992Date of Patent: April 5, 1994Assignee: Hoechst AktiengesellschaftInventors: Jorg Dannheim, Werner H. Russ
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Patent number: 5298607Abstract: The invention provides reactive dyes of the formula ##STR1## wherein D is a mono- or polyazo, metal complex azo, anthraquinone, phthalocyanine, formazane, dioxazine or stilbene dye which contains sulfo groups, R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.2 is hydrogen, methyl or ethyl, X is a radical of the formula --SO.sub.2 CH.sub.2 CH.sub.2 Cl, --SO.sub.2 CH.dbd.CH.sub.2, --SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H, --SO.sub.2 CH.sub.2 CH.sub.2 OPO.sub.3 H or --N(R.sub.3)SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H, and R.sub.3 is hydrogen, methyl or ethyl, and the benzene or naphthalene radical is not further substituted or is further substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.Type: GrantFiled: May 26, 1993Date of Patent: March 29, 1994Assignee: Ciba-Geigy CorporationInventor: Herbert Seiler
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Patent number: 5292870Abstract: A compound which, in the free acid form, is of Formula (1): ##STR1## wherein: Z is vinyl, or an ethyl group having a substituent at the 2-position which is capable of being eliminated in the presence of alkali to give a vinyl group;D is substituted or unsubstituted phenylene or naphthylene;K is the residue of a coupling component;R.sup.1 is H, alkyl or substituted alkyl;R.sup.2 is alkyl or substituted alkyl;X is halo or quaternary ammonium; andL is substituted or unsubstituted phenylene.The compound is useful as a dye for the coloration of, for example, cotton, on which it has excellent build up, good fixation efficiency and good wash off properties.Type: GrantFiled: November 8, 1991Date of Patent: March 8, 1994Assignee: Imperial Chemical Industries PLCInventor: Kenneth Anderton
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Patent number: 5278292Abstract: Water-soluble fiber-reactive dyes are described conforming to the below-indicated formula (1) which are capable of dyeing hydroxyl- and/or carboxamido-containing material, in particular fiber material, such as wool and in particular cellulose fiber materials, in strong, fast shades. ##STR1## in which F is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, triphenoldioxazine, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, formazan, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye;R.sup.x is hydrogen or alkyl of 1 to 4 carbon atoms;R is hydrogen, sulfo, carboxyl, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or chlorine;w is 1, 2, 3 or 4;Y is vinyl or an ethyl group which contains in the .beta.-position a substituent which is eliminable by alkali to form a vinyl group;n is 1 or 2.Type: GrantFiled: July 17, 1992Date of Patent: January 11, 1994Assignee: Hoechst AktiengesellschaftInventors: Hartmut Springer, Rolf Gleissner, Gunther Schwaiger
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Patent number: 5276148Abstract: Reactive dyes of the formula ##STR1## where n is 0 or 1,R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,A is unsubstituted or substituted C.sub.2 -C.sub.8 -alkylene,Y is vinyl or a radical of the formula --CH.sub.2 --CH.sub.2 --Q, whereQ is a group which can be eliminated under alkaline reaction conditions,D.sup.1 is phenyl or naphthyl, where these radicals may be substituted,D.sup.2 is phenylene or naphthylene, where these radicals may be substituted, andZ is a reactive radical,with the proviso thata) n is zero when D.sup.1 is substituted by unsubstituted or substituted phenylazo or by unsubstituted or substituted naphthylazo andb) the reactive radical Z is not devised from the triazine series when n is zero and D.sup.1 is dihydroxysulfonylphenyl or trihydroxysulfonylnaphthyl,are used for dyeing and printing organic substrates containing hydroxyl groups or nitrogen atoms.Type: GrantFiled: May 22, 1992Date of Patent: January 4, 1994Assignee: BASF AktiengesellschaftInventors: Bernd Siegel, Manfred Patsch
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Patent number: 5268457Abstract: Reactive dyes of the formula ##STR1## are particularly suitable for dyeing or printing cellulosic fibre materials by the exhaust method or by continuous processes and give, with a high color yield, dyeings and prints with good fastness properties, in which D is 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 is hydrogen or alkyl having 1 to 4 carbon atoms, which can be substituted by hydroxyl, cyano, carboxyl, sulfo or sulfato; X is fluorine or chlorine; B is a substituted or unsubstituted aliphatic or aromatic bridge member; Y is a substituted or unsubstituted aliphatic, aromatic, araliphatic or heterocyclic radical, which is free from reactive groups; R.sub.2 is hydrogen or alkyl having 1 to 4 carbon atoms, which can be substituted by halogen, hydroxyl, cyano, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.Type: GrantFiled: December 28, 1992Date of Patent: December 7, 1993Assignee: Ciba-Geigy CorporationInventor: Athanassios Tzikas
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Patent number: 5268458Abstract: Azo compounds containing, as the diazo constituent, 1-sulpho-6-carboxy-2-aminonaphthalene and, as the coupling constituent, substances which contain a residue of the pyrimidine or triazine series which reacts with fibers. The azo compounds possess dye properties and, when used in the usual application fixing process for fiber-reactive dyes, color materials containing carbonamide and/or hydroxyl groups, in particular fibrous material such as wool, synthetic nylon and, in particular, cellulose fiber materials in intense, permanent shades.Type: GrantFiled: June 25, 1992Date of Patent: December 7, 1993Assignee: Hoechst AktiengesellschaftInventors: Hartmut Springer, Kurt Hussong
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Patent number: 5256774Abstract: Improved reactive dyestuffs have the following formula ##STR1## in which the substituents have the meaning given in the description.Type: GrantFiled: February 20, 1992Date of Patent: October 26, 1993Assignee: Bayer AktiengesellschaftInventors: Wolfgang Harms, Thomas Eizenhofer
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Patent number: 5250670Abstract: There are described monoazo compounds which exhibit fiber-reactive properties and dye hydroxy- and/or carboxamido-containing materials, in particular fiber materials, such as, for example, cellulose fiber materials and wool, in shades of high color strength and good fastness properties and can also be used in particular for resist and discharge printing. They have the formula (1) ##STR1## in which: A is substituted or unsubstituted phenylene or unsubstituted or sulfo-substituted naphthylene, the groups X--SO.sub.2 -- and --SO.sub.2 X.sup.1 are fiber-reactive groups from the vinylsulfonyl series, n is the number 1 or 2, M is hydrogen or an alkali metal, R is hydrogen or a lower alkyl, W is phenylene or lower alkylene, B is lower alkyl and one group --SO.sub.3 M is bound to the 8-naphthol radical in the 3- or 4-position.Type: GrantFiled: September 24, 1992Date of Patent: October 5, 1993Assignee: Hoechst AktiengesellschaftInventors: Ludwig Schlafer, Werner H. Russ
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Patent number: 5241056Abstract: Reactive dyestuffs of the formula ##STR1## and the meanings of substituents given in the description produce on hydroxyl- and amido-containing fibre materials orange dyeings which are fast to boiling.Type: GrantFiled: May 4, 1992Date of Patent: August 31, 1993Assignee: Bayer AktiengesellschaftInventors: Manfred Hoppe, Karl-Josef Herd, Hermann Henk
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Patent number: 5239063Abstract: Fiber reactive azo dyestuffs of the formula ##STR1## in which R=H or C.sub.1 -C.sub.6 alkyl, which can be substituted with OH, Hal, SO.sub.3 H or OSO.sub.3 H;Z=heterocyclic five or six membered ring;n, m=0, 1 or 2, wherein n+m=0, 1 or 2;Y=OH, OR, NR.sub.2 R.sub.3, OMe; andR.sub.2, R.sub.3, =H, R and R.sub.2, R.sub.3 and N can form a heterocyclic 5 or 6-membered ring.Type: GrantFiled: January 9, 1992Date of Patent: August 24, 1993Assignee: Bayer AktiengesellschaftInventors: Manfred Hoppe, Martin Michna, Karl-Josef Herd, Frank-Michael Stohr
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Patent number: 5233026Abstract: Reactive dyes of the formula ##STR1## in which D is a monoazo dye, R.sub.1 is hydrogen or a substituted or unsubstituted C.sub.1-4 alkyl radical, Z is an unsubstituted or substituted amino group, and X is a vinyl, .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-chloroethyl or .beta.-acetoxyethyl group, with the condition that Z is not a sulfo- or carboxyl-substituted phenylamino group when the triazine radical is bonded to the radical of 1,8-aminonaphthol-3,6- or -4,6-disulfonic acid, and the X--SO.sub.2 radical is bonded directly to an aromatic C atom, are suitable in particular for dyeing and printing cellulose-containing fiber materials by the cold pad-batch method and produce, in high dyeing yields, dyeings and prints having good fastness properties.Type: GrantFiled: August 2, 1991Date of Patent: August 3, 1993Assignee: Ciba-Geigy CorporationInventor: Athanassios Tzikas
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Patent number: 5231171Abstract: Reactive dyes useful for dyeing or printing hydroxyl- or nitrogen-containing substrates have the formula ##STR1## where Rg is a radical of the formula ##STR2## Ar is the radical of a benzene or naphthalene ring, Z.sup.1 and Z.sup.2 are each hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, substituted or unsubstituted phenyl, C.sub.1 -C.sub.4 -alkoxy, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, cyano, halogen or hydroxysulfonyl,Z.sup.3, Z.sup.4 and Z.sup.5 are each hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or substituted or unsubstituted phenyl,U is a group which is detachable under alkaline reaction conditions,X is in case a) the radical of a chromophore or in case b) the radical of a coupling component to which may additionally be attached, via an azo bridge, the radical of a diazo component and which may have additional reactive groups, andL is in case a) a bridge member or in case b) an azo bridge.Type: GrantFiled: December 13, 1991Date of Patent: July 27, 1993Assignee: BASF AktiengesellschaftInventors: Claus Marschner, Matthias Niedenbrueck, Bernd Siegel, Manfred Patsch, Klaus Pandl
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Patent number: 5227478Abstract: Compounds of the formula ##STR1## in which either and salts thereof R.sub.1 is hydrogen or hydroxy-C.sub.2-3 alkyl, andR.sub.2 is hydroxy-C.sub.2-3 alkyl, orR.sub.1 is hydrogen or 2-cyanoethyl, andR.sub.2 is --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OH,and mixtures of such compounds, which compounds are in free acid or salt form, are useful for dyeing or printing hydroxy group- or nitrogen-containing organic substrates, particularly leather and textiles containing or consisting of natural or synthetic polyamides or of natural or regenerated cellulose, especially textile material containing or consisting of cotton.Type: GrantFiled: January 24, 1992Date of Patent: July 13, 1993Assignee: Sandoz Ltd.Inventor: Werner Koch
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Patent number: 5227475Abstract: Water-soluble dyestuffs which correspond to the formula (1) given below, have fiber-reactive properties and dye synthetic and natural materials, in particular fiber materials, containing hydroxyl and/or carboxamide groups, such as wool and in particular cellulose fiber materials, in deep shades ##STR1## in which: F is the radical of a dyestuff, such as of an azo dyestuff, heavy metal complex azo dyestuff, anthraquinone dyestuff or phthalocyanine dyestuff,R.sup.x is hydrogen or lower alkyl, which can be substituted by halogen, hydroxyl, cyano, lower alkoxy, lower alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato;n is the number 1 or 2; andQ is a group of the formula ##STR2## in whichR.sup.Type: GrantFiled: January 10, 1992Date of Patent: July 13, 1993Assignee: Hoechst AktiengesellschaftInventors: Holger M. Buch, Reinhard Hahnle, Hartmut Springer
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Patent number: 5216137Abstract: Azo reactive dyes useful for dyeing or printing hydroxyl- or nitrogen-containing substrates have the formula ##STR1## where m is 0, 1 or 2,n is 0 or 1,p is 0 or 1,R.sup.1 and R.sup.2 are each independently of the other hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl,R.sup.3 is hydrogen, methyl or ethyl,T is carboxyl or hydroxysulfonyl,Hal is fluorine or chlorine, andthe ring A may be benzofused or substituted.Type: GrantFiled: July 5, 1991Date of Patent: June 1, 1993Assignee: BASF AktiengesellschaftInventors: Hermann Loeffler, Manfred Patsch, Reinhold Krallmann
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Patent number: 5210187Abstract: Double attachment reactive dyes have the formula ##STR1## where U.sup.1 is C.sub.1 -C.sub.4 -alkyl, phenyl, C.sub.2 -C.sub.10 -alkenyl or the radical ##STR2## where Q.sup.1 and Q.sup.2 are each independently of the other hydrogen or C.sub.1 -C.sub.4 -alkyl and Q.sup.3 is a group which is detachable under alkaline reaction conditions,Z is the radical ##STR3## where each Q.sup.4 is independently of the other hydrogen or C.sub.1 -C.sub.4 -alkyl which may be substituted by cyano, U.sup.2 is C.sub.1 -C.sub.4 -alkyl, phenyl, C.sub.2 -C.sub.10 -alkenyl or the radical ##STR4## where Q.sup.5 and Q.sup.6 are each independently of the other hydrogen or C.sub.1 -C.sub.4 -alkyl and Q.sup.7 is a group which is detachable under alkaline reaction conditions, and w is 0, 1 or 2,t is 0, 1 or 2,v is 1 or 2 and X and L are each as defined in the description, with the proviso that at least one of the two radicals U.sup.1 and U.sup.2 is not C.sub.1 -C.sub.Type: GrantFiled: April 9, 1992Date of Patent: May 11, 1993Assignee: BASF AktiengesellschaftInventors: Manfred Patsch, Uwe Nahr, Friedrich Wirsing, Joerg L. Jessen, Klaus Pandl, Claus Marschner, Matthias Dust
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Patent number: 5189206Abstract: There is disclosed a process for the preparation of compounds of formula ##STR1## wherein the symbols are as defined in claim 1, which process comprises dissolving a compound of formula ##STR2## in sulfuric acid, adding this solution to oleum and reacting the mixture in the temperature range from 10.degree. to 80.degree. C. until a sulfo group has been completely introduced, and, in an optional further step, subjecting the reaction mixture to further reaction in the temperature range from 100.degree. to 200.degree. C. to introduce a second sulfo group.The compounds of formula (1) obtainable by this process are useful intermediates for the synthesis of dyes and are particularly suitable diazo components for the synthesis of azo dyes.Type: GrantFiled: August 12, 1991Date of Patent: February 23, 1993Assignee: Ciba-Geigy CorporationInventor: Paul Herzig
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Patent number: 5175263Abstract: Azo compounds with fiber-reactive dye properties, having defined general formula (1) below, are described which dye fiber materials containing hydroxy and/or carboxamide groups, such as synthetic polyamide fibers or wool, and especially cellulose fiber materials such as cotton, in strong, fast, predominantly red shades. ##STR1## in which: X is vinyl or .beta.-sulfatoethyl;T is a direct bond or the methylene or divalent methyl amino group;D is phenylene which is unsubstituted or substituted by lower alkyl, lower alkoxy, chlorine, bromine, sulfo and/or carboxy, or is an unsubstituted or sulfo-substituted naphthylene or a group of the formula ##STR2## R is phenyl which is unsubstituted or substituted by hydroxy lower alkyl, lower alkoxy, carboxy and/or sulfo, or is a lower alkyl substituted by unsubstituted or sulfo-substituted phenyl or by unsubstituted or sulfo-substituted naphthyl; andM is a hydrogen atom or an alkali metal.Type: GrantFiled: February 14, 1991Date of Patent: December 29, 1992Assignee: Hoechst AktiengesellschaftInventor: Ludwig Schlafer
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Patent number: 5149791Abstract: Novel reactive dyes of the formula ##STR1## in which Z is a radical of the formula ##STR2## in which R.sub.1 and R.sub.2 independently of one another are hydrogen or C.sub.1 -C.sub.6 alkyl, which can be substituted by C.sub.1 -C.sub.4 alkoxy, hydroxy-C.sub.1 -C.sub.4 alkoxy, HO--(CH.sub.2 CH.sub.2 --O).sub.2-4 --, C.sub.1 -C.sub.4 alkoxy-carbonyl, C.sub.2 -C.sub.4 alkanoyloxy, carboxyl, cyano, chlorine, sulfo or sulfato, n is the number 0, 1 or 2 and m is the number 1 or 2, (Q.sub.1).sub.m is 1 or 2 substituents Q.sub.1 independent of one another from the group comprising C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, acetylamino and carboxyl, (Q.sub.2).sub.n is 0 to 2 substituents Q.sub.2 and (Q.sub.2).sub.m is 1 or 2 substituents Q.sub.2 independent of one another from the group comprising C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.Type: GrantFiled: October 26, 1990Date of Patent: September 22, 1992Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Urs Lauk
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Patent number: 5149789Abstract: Reactive dyes of the formula ##STR1## where 1 is 0 or 1,n is 0 or 1,E is nitrogen or C--Cl,A is the radical of an azo dye attached to the triazine ring via an imino or C.sub.1 -C.sub.4 -alkylimino group,B--if E is nitrogen--is the radical of an azo dye or of a formazan dye which in either case is bonded to the triazine ring via an imino or C.sub.1 -C.sub.4 -alkylimino group or else--if n is 0--is fluorine, chlorine or unsubstituted or substituted amino, or --if E is C--C1--is fluorine, chlorine or methyl,X.sup.1 and X.sup.2 are independently of the other fluorine or chlorine,X.sup.3 is fluorine or chlorine or else--if E is C--Cl--methylsulfonyl andZ.sup.1 and Z.sup.2 are independently of the other a radical of the formula ##STR2## where L.sup.3 and L.sup.4 are independently of the other hydrogen or unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl,with the proviso that l and n are not simultaneously 0 and that, if E is C--Cl or if n is 0 and Z.sup.1 is the radical of the formula ##STR3## where L.sup.Type: GrantFiled: March 8, 1990Date of Patent: September 22, 1992Assignee: BASF AktiengesellschaftInventors: Joerg L. Jessen, Klaus Pandl, Hermann Loeffler, Bernd Siegel, Manfred Patsch
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Patent number: 5136028Abstract: Novel reactive dyes of formula ##STR1## wherein Z is a radical of formula ##STR2## and R.sub.1, R.sub.2, R.sub.3, (R.sub.4).sub.2-3, (R.sub.5).sub.1-3, R.sub.7 and (R.sub.8).sub.1-3 are as defined in claim 1, give intense red dyeings and prints of good fastness properties on cellulosic fibres.Type: GrantFiled: November 9, 1990Date of Patent: August 4, 1992Assignee: Ciba-Geigy CorporationInventor: Herbert Seiler
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Patent number: 5128456Abstract: Novel reactive dyes of the formula ##STR1## in which (R).sub.0-3 is 0-3 substituents R, independent of one another, from the group comprising halogen, nitro, cyano, trifluoromethyl, sulfamoyl, carbamoyl, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, amino, acetylamino, ureido, hydroxyl, carboxyl, sulfomethyl and sulfo, R.sub.1 is hydrogen, C.sub.1-8 alky or C.sub.5-7 cycloalkyl and R.sub.2 is C.sub.1-8 alkyl or C.sub.5-7 cycloalkyl, it being possible for the alkyl and cycloalkyl radicals R.sub.1 and R.sub.2 to be substituted independently of one another by hydroxyl, C.sub.1-4 alkoxy, hydroxy-C.sub.1-4 alkoxy, HO--(CH.sub.2 CH.sub.2 --O).sub.2-4 --, sulfato-C.sub.1-4 alkoxy, C.sub.2-4 alkanoyl, C.sub.1-4 alkoxy-carbonyl, C.sub.2-4 alkanoyloxy, carboxyl, cyano, halogen, C.sub.1-4 alkylamino, or N,N-Di-C.sub.1-4 alkylamino, or sulfato, or in which R.sub.1 is C.sub.1-8 alkyl or C.sub.5-7 cycloalkyl, and the alkyl or cycloalkyl radical can be substituted as defined, and R.sub.2 is a C.sub.1-8 alkyl or C.sub.Type: GrantFiled: October 26, 1990Date of Patent: July 7, 1992Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Paul Herzig
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Patent number: 5116957Abstract: Reactive azo dyestuffs of the formula ##STR1## wherein R, Z and A have the meaning indicated in the description, and their use for dyeing and printing materials containing hydroxyl groups or amide groups, such as textile fibers, filaments and fabrics of wool, silk and synthetic polyamide fibers and polyurethane fibers, and for dyeing and printing natural or regenerated cellulose in shades which are fast to washing.Type: GrantFiled: October 25, 1990Date of Patent: May 26, 1992Assignee: Bayer AktiengesellschaftInventor: Horst Jager
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Patent number: 5116959Abstract: A monoazo compound represented by the following formula in a free acid form, ##STR1## wherein R is hydrogen or unsubstituted or substituted C.sub.1 to C.sub.4 alkyl, X is unsubstituted or substituted phentyl or naphthyl, Y is unsubstituted or substituted phenylene or naphthylene, Z is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z.sub.1, in which Z.sub.1 is a splittable group by the action of an alkali, and R.sub.1 and R.sub.2 are independently hydrogen or unsubstituted or substituted C.sub.1 to C.sub.4 alkyl, phenyl or benzyl, excepting the case where R.sub.1 and R.sub.2 are hydrogen, which is useful as reactive dyes of high solubility and good build-up property for giving dyed or printed products of a deep red color excellent in fastness properties.Type: GrantFiled: March 9, 1987Date of Patent: May 26, 1992Assignee: Sumitomo Chemical Company, LimitedInventors: Toshihiko Morimitsu, Naoki Harada, Takashi Omura, Sadanobu Kikkawa
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Patent number: 5106960Abstract: The present invention relates to azo dyes of the formula ##STR1## wherein X is an aryloxy radical or an unsubstituted or substituted C.sub.1 -C.sub.12 alkyl radical, a cycloalkyl radical or an aryl radical or a group of the formula ##STR2## wherein R.sub.1 is hydrogen, unsubstituted or substituted lower alkyl, cycloalkyl or aryl, and R.sub.2 is hydrogen or unsubstituted or substituted lower alkyl, or wherein R.sub.1 and R.sub.2, together with the nitrogen atom to which they are attached, form a 5- or 6-membered heterocyclic ring which may contain a further hetero-atom, Y is halogen, low molecular alkyl or low molecular alkoxy, and K is the radical of a coupling component of the benzene or naphthalene series or of the heterocyclic series.These dyes yield dyeings of good light- and wetfastness on polyamide material.Type: GrantFiled: March 22, 1991Date of Patent: April 21, 1992Assignee: Ciba-Geigy CorporationInventors: Rudolf Hurter, Dieter Mausezahl
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Patent number: 5095102Abstract: Reactive dyestuffs of the formula ##STR1## in which A=H, halogen, alkyl, alkoxy, acylamino or amino,B=H, alkyl or alkoxy,X=--CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --Y, whereY=a radical which can be removed under alkaline conditions andZ=a fibre-reactive radical.Type: GrantFiled: August 13, 1990Date of Patent: March 10, 1992Assignee: Bayer AktiengesellschaftInventors: Karl-Josef Herd, Manfred Hoppe, Hermann Henk, Rolf Brockmann, Frank-Michael Stohr
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Patent number: 5093482Abstract: Reactive dyestuffs of the formula ##STR1## in which the R=C.sub.1 -C.sub.5 -alkyl, cyclohexyl or aryl,R.sub.1 =H or sulpho, halogen (Cl, Br) or C.sub.1 -C.sub.4 -alkyl, gives scarlet dyeings, which are fast to boiling, on fibre materials containing hydroxyl and amide groups.Type: GrantFiled: August 27, 1991Date of Patent: March 3, 1992Assignee: Bayer AktiengesellschaftInventors: Karl H. Schundehutte, Frank-Michael Stohr
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Patent number: 5091515Abstract: A new process for the preparation of substituted 2,4-diamino-6-flurotriazines of the formula ##STR1## in which the substituents have the meanings given in the description, comprises reacting ammonium salts of the formula ##STR2## in an aqueous medium at pH values of about 2.5-10 with 2,4,6-trifluorotriazine in a continuous process. The reaction products can be converted to dyestuffs without isolating the intermediates.Type: GrantFiled: May 3, 1990Date of Patent: February 25, 1992Assignee: Bayer AktiengesellschaftInventors: Karl J. Herd, Hans-Georg Frosch, Hermann Henk, Wolfgang Mullers, Frank-Michael Stohr
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Patent number: 5091516Abstract: Reactive dyes useful for dyeing or printing hydroxyl- or amino-containing organic substrates have the formula ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,R.sup.4 is C.sub.1 -C.sub.4 -alkoxy, phenoxy or a radical of the formula NL.sup.1 L.sup.2, where L.sup.1 and L.sup.2 are each substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or substituted or unsubstituted phenyl, or L.sup.1 and L.sup.2 together combine with the nitrogen atom joining them to form a heterocyclic radical, or L.sup.1 may also be hydrogen,R.sup.5 is fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl or a radical of the formula ##STR2## A is substituted or unsubstituted C.sub.2 -C.sub.8 -alkylene, Y is vinyl or a radical of the formula --CH.sub.2 --CH.sub.Type: GrantFiled: November 5, 1990Date of Patent: February 25, 1992Assignee: BASF AktiengesellschaftInventors: Bernd Siegel, Manfred Patsch
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Patent number: 5073631Abstract: Reactive dyes of the formulaX.sub.1 --NH--CH.sub.2).sub.0-1 A--N.dbd.N--M--N.dbd.N--B--CH.sub.2).sub.0-1 NH--X.sub.2 (1)in which M is twice-coupled 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid, 1-amino-8-hydroxynaphthalene-4,6-disulfonic acid, 1-amino-8-hydroxynaphthalene-4-sulfonic acid or 2-amino-5-hydroxynaphthalene-7-sulfonic acid, A and B, independently of each other, are each unsubstituted or substituted phenylene or naphthylene, and X.sub.1 and X.sub.2, independently of each other, are each unsubstituted or substituted amino-fluoro-1,3,5-triazinyl, excluding the reactive dyes of German Offenlegungsschrift 2,738,823, are suitable in particular for dyeing and printing cellulose-containing fibre materials and produce, combined with a high dyeing yield, dyeings and prints having good fastness properties.Type: GrantFiled: September 14, 1988Date of Patent: December 17, 1991Assignee: Ciba-Geigy CorporationInventor: Peter Scheibli
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Patent number: 5047514Abstract: Reactive dyes which contain at least one radical of the formula--SO.sub.2 --CH.dbd.CH.sub.2 (1a)or--SO.sub.2 --CH.sub.2 CH.sub.2 --X (1b)and at least one radical of the formula ##STR1## in which X is an inorganic or organic radical detachable under alkaline conditions, R is hydrogen or substituted or unsubstituted C.sub.1-4 -alkyl, Y is oxygen or sulfur and R.sub.1 is a substituted or unsubstituted aliphatic radical, give dyeings or prints having good fastness properties.Type: GrantFiled: November 5, 1987Date of Patent: September 10, 1991Assignee: Ciba-Geigy CorporationInventors: Peter Scheibli, Karl Seitz
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Patent number: 5047515Abstract: Monoazo compounds which conform to the general formula (1) given below and are used as fiber-reactive dyes for dyeing carboxamido-containing and/or hydroxy-containing materials, for example wool, synthetic polyamide fibers and in particular cellulose fibers, in fast, predominantly yellowish red, red and orange shades.Type: GrantFiled: May 21, 1990Date of Patent: September 10, 1991Assignee: Hoechst AktiengesellschaftInventors: Hartmut Springer, Kurt Hussong
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Patent number: 5037965Abstract: A monoazo compound represented by the following formula in the free acid form, ##STR1## wherein D is phenylene or naphthylene, R is hydrogen or alkyl, A is phenylene or naphthylene, Z.sub.1 and Z.sub.2 independently of one another are each vinylsulfonyl, .beta.-sulfatoethylsulfonyl and the like, and X is pyridinio or amino represented by the following formula ##STR2## wherein R.sub.1 and R.sub.2 independently of one another are each hydrogen, alkyl, phenyl, naphthyl or benzyl, which is useful for dyeing or printing fiber materials to give dyed or printed products of red color excellent in fastness properties with excellent build-up, level-dyeing and washing-off properties.Type: GrantFiled: November 21, 1988Date of Patent: August 6, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Toshihiko Morimitsu, Kingo Akahori, Yutaka Kayane, Naoki Harada, Takashi Omura
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Patent number: 5032140Abstract: A reactive dye represented by the formula (I), ##STR1## wherein R represents --NH.sub.2 or --NHC.sub.2 H.sub.4 SO.sub.3 M, and M's independently represent Li.sup..sym., Na.sup..sym., K.sup..sym. or .sup..sym. NH(C.sub.2 H.sub.4 OH).sub.3, provided that at least one of M's represents Li.sup..sym. or .sup..sym. NH(C.sub.2 H.sub.4 OH).sub.3. This reactive dye easily gives a stable liquid composition and is useful to dye cellulosic or polyamide fibers.Type: GrantFiled: October 24, 1989Date of Patent: July 16, 1991Assignee: Nippon Kayaku Kabushiki KaishaInventors: Nobuyuki Yamanaka, Kazuo Hanawa, Eiichi Ogawa
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Patent number: 5023326Abstract: Reactive dyes of the formula ##STR1## in which Y is hydrogen or sulfo, U is --CN, --CONH.sub.2, --SO.sub.3 H, --OH or --OSO.sub.3 H, D is a phenyl or naphthyl radical, which can be substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl and sulfo, and which contains at least one reactive radical bound direclty or via a bridge member to a ring carbon atom, or to which a further radical is bound which contains a reactive radical, and u is the number 2, 3, 4 or 5, are suitable in particular for the dyeing or printing of cellulose-containing fiber materials by the exhaust method or by the continuous method and product in combination with a high colorisitc yield dyeings and prints which have good fastness properties.Type: GrantFiled: November 9, 1989Date of Patent: June 11, 1991Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Herbert Seiler
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Patent number: 5021558Abstract: Water-soluble fiber-reactive azo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylemthane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dyes which contain once or twice the group of the general formula ##STR1## in which: R.sup.x and R.sup.z are, independently of one another, hydrogen or lower alkyl, which can be substituted by halogen, hydroxyl, cyano, lower alkoxy, lower alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato;W is fluorine, chlorine, bromine, sulfo, phenylsulfonyl or alkylsulfonyl of 1 to 4 carbon atoms;Y is vinyl, .beta.-substituted, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-alkanoyloxyethyl of 2 to 5 carbon atoms in the alkanoyl radical, .beta.-benozoyloxyethyl, .beta.-(sulfobenzoyloxy)ethyl, .beta.-(p-toluenesulfonyloxy)ethyl or .beta.-halogenoethyl.Type: GrantFiled: March 20, 1990Date of Patent: June 4, 1991Assignee: Hoechst AktiengesellschaftInventor: Holger M. Buch
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Patent number: 5021559Abstract: Water-soluble azo compounds of the general formula D--N.dbd.N--K are described, which have advantageous fiber-reactive dye properties and dye carboxamido-containing and in particular hydroxy-containing materials, such as wool and in particular cellulose fiber materials, in hues which have high color strength and good fastness properties.In the formula D--N.dbd.N--K, the symbols have the following meanings:D is a radical of the general formula ##STR1## in which Y is a vinyl group or an ethyl group which can be eliminated in the .beta.Type: GrantFiled: May 21, 1990Date of Patent: June 4, 1991Assignee: Hoechst AktiengesellschaftInventors: Hartmut Springer, Uwe Reiher
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Patent number: 5010180Abstract: Water-soluble azo compounds corresponding to the general formula D--N.dbd.N--K which have advantageous fiber-reactive dyestuff properties and dye materials containing carboxamide groups and in particular materials containing hydroxy groups, such as wool and in particular cellulose fiber materials, in deep fast shades are described.In the formula D--N.dbd.N--K:D is a radical of the general formula ##STR1## in which Y is the vinyl group or an ethyl group in the .beta.Type: GrantFiled: February 1, 1990Date of Patent: April 23, 1991Assignee: Hoechst AktiengesellschaftInventors: Hartmut Springer, Uwe Reiher
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Patent number: 5006645Abstract: Dyes of the formula ##STR1## wherein K is the radical of a coupling component which can additionally contain azo groups, R is hydrogen or methyl, and Z is a fluorine atom, a substituted or unsubstituted amino group, a substituted or unsubstituted hydroxyl group, a substituted or unsubstituted mercapto group, or a substituted or unsubstituted hydrocarbon radical are distinguished by high reactivity and they produce dyeings of good wet- and light-fastness properties. The dyes of the Formula (I) are suitable for dyeing and printing a very wide variety of materials, such as silk, leather, wool, polyamide and polyurethane fibres, and especially cellulosic materials of fibrous structure, such as liner, cellulose, regenerated cellulose, and in particular cotton. They are suitable both for the exhaust method and for dyeing by the pad-dyeing process. They are also suitable for printing, in particular on cotton.Type: GrantFiled: September 14, 1989Date of Patent: April 9, 1991Assignee: Ciba-Geigy CorporationInventor: Karl Seitz
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Patent number: 5003052Abstract: A reactive dye of the formula ##STR1## in which R is a radical of the formula ##STR2## or Z is .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-acetoxyethyl, .beta.-halogenoethyl or vinyl; V is hydrogen or a radicalZ--SO.sub.2 --CH.sub.2 --CH.sub.2 --in which z is as defined above; R.sub.1 is hydrogen or C.sub.1-6 -alkyl; alk, independently of each other, are polymethylene radicals having 2 to 6 C atoms or their branched isomers; K is a benzene, naphthalene or heterocyclic radical; m is 1 to 6, p is 1 to 6 and q is 1 to 6; and the benzene or naphthalene radical A is further unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.8 -acylamino, C.sub.1 -C.sub.4 -alkylamino, phenylamino, N,N-di-.beta.-hydroxyethylamino, N,N-di-.beta.-sulfatoethylamino, sulfobenzylamino, N,N-disulfobenzylamino, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkylsulfonyl, trifluoromethyl, nitro, cyano, halogen, carbamoyl, N-C.sub.1 -C.sub.Type: GrantFiled: May 11, 1988Date of Patent: March 26, 1991Assignee: Ciba-Geigy CorporationInventor: Athanassios Tzikas
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Patent number: 5003053Abstract: Water-soluble monoazo compounds of the general formula (1) which dye in fast, mainly red shades materials which contain carboxamide and/or hydroxy groups, preferably in the form of fibers, in particular cellulose fiber materials. ##STR1## in which: Y is .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-chloroethyl, vinyl or .beta.-sulfatoethyl,M is hydrogen, an alkali metal or an alkaline-earth metal,D is naphthyl which is substituted by sulfo and/or a group of the formula Y--SO.sub.2 --,or is one of the radicals ##STR2## in which M and Y have one of the above meanings, m is the number zero or 1, R.sup.1 is hydrogen, lower alkyl, lower alkoxy or carboxy, and R.sup.2 is hydrogen, lower alkyl, lower alkoxy, sulfo, carboxy, optionally substituted aryl, hydroxy, nitro or halogen,n is the number zero or 1,R is hydrogen or optionally substituted lower alkyl,R* is hydrogen or optionally substituted lower alkyl,X is fluorine or chlorine,B is a group of the formula ##STR3## in which R.sup.Type: GrantFiled: March 19, 1990Date of Patent: March 26, 1991Assignee: Hoechst AktiengesellschaftInventors: Hartmut Springer, Walter Helmling, Ludwig Schlafer, Werner H. Russ
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Patent number: 4996304Abstract: Reactive dyes of the formula ##STR1## in which D is the radical of a dye of the polyazo or metal complex azo series, R.sub.1 is hydrogen or an unsubstituted or substituted C.sub.1-4 -alkyl radical, and X is the vinyl, .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-chloroethyl or .beta.-acetoxyethyl group, are suitable in particular for dyeing and printing cellulose-containing fibre materials by the cold pad-batch method and produce, in high dyeing yields, dyeings and prints having good fastness properties.Type: GrantFiled: February 23, 1990Date of Patent: February 26, 1991Assignee: Ciba-Geigy CorporationInventor: Athanassios Tzikas
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Patent number: 4994562Abstract: The fibre-reactive formazan dyes of the formula ##STR1## where B is an aliphatic or sulfo-free aromatic bridge member, R is .alpha.,.beta.-dihalopropionyl, .alpha.-haloacryloyl or haloacetyl, T.sub.1 is halogen, X is halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, cyano or nitro, Y is --CO-- or --SO.sub.2 --, Z is nitrogen or --C--T.sub.2, T.sub.2 is halogen, hydrogen, C.sub.1 -C.sub.4 alkylthio, cyano, formyl or C.sub.1 -C.sub.4 alkylsulfonyl, m is 1, 2 or 3, n is 0, 1 or 2, qu is 0 or 1 and r and s are each eitehr 0 or 1 but never the same as each other, produce dyeings having good fastness properties on nitrogen-containing or hydroxyl-containing fibre materials.Type: GrantFiled: June 29, 1989Date of Patent: February 19, 1991Assignee: Ciba-Geigy CorporationInventor: Urs Lehmann
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Patent number: 4988803Abstract: An azo dyestuff of the formula ##STR1## in which u and v=H or SO.sub.3 H and u.noteq.v,R=H, unsubstituted C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkyl substituted by OH, halogen, SO.sub.3 H or OSO.sub.3 H,m=0 or 1 and ##STR2## in which R.sub.1 =H, unsubstituted C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -alkyl substituted by OH, OSO.sub.3 H, SO.sub.3 H or COOH. Such dye is particularly suitable for producing on cotton red dyeings and prints having excellent fiber-dyestuff bond stability, stability to oxidizing agents and wash-off properties.Type: GrantFiled: January 5, 1990Date of Patent: January 29, 1991Assignee: Bayer AktiengesellschaftInventors: Frank M. Stohr, Hermann Henk, Karl-Josef Herd
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Patent number: 4988801Abstract: A water-soluble monoazo colorant represented by formula (I) in a form of a free acid: ##STR1## wherein D represents ##STR2## (wherein W.sup.2 represents lower alkoxy; U represents lower alkyl or lower alkoxy; Z represents --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 OSO.sub.3 H and p and q represent each 0 or 1);W.sup.1 represents lower alkoxy; andV represents ##STR3## (wherein X represents halogen; Y represents halogen, sulfo, --OR.sup.1 wherein R.sup.1 represents lower alkyl or lower alkyl substituted by hydroxy, carboxy or sulfo, --O--R.sup.2 O).sub.m R.sup.3 alkyl and m is an integer of 1 to 6, or aliphatic or aromatic amino each substituted by one or two sulfo or carboxy groups);as well as a dyeing process by using the same. These colorants are useful in the dyeing of fibers. These colorants are useful in the dyeing of fibers.Type: GrantFiled: December 20, 1989Date of Patent: January 29, 1991Assignee: Mitsubishi Kasei CorporationInventors: Toshio Hihara, Kanzi Shimizu, Yukiharu Shimizu
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Patent number: 4975530Abstract: Intermediates useful for the preparation of fiber-reactive dyes having the formula ##STR1## in which Q is phenyl unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, nitro, cyano, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylsulfonyl, sulfo or trihalomethyl; 1- or 2-naphthyl; or unsubstituted or C.sub.1 -C.sub.4 alkyl, nitro, cyano, C.sub.1 -C.sub.4 alkoxycarbonyl or C.sub.1 -C.sub.4 alkylthio substituted furanyl, thienyl, thiazolyl, oxazolyl, isothiazolyl, benzothiazolyl, benzoisothiazolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl or 1,3,5-triazinyl, and A.sub.1 and A.sub.2 independently of one another are a radical of the formula ##STR2## in which R.sub.1 and R.sub.2 independently of one another are hydrogen; C.sub.1 -C.sub.4 alkyl unsubstituted or substituted by hydroxyl, sulfo, sulfato, carboxyl, cyano, halogen, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.Type: GrantFiled: November 22, 1989Date of Patent: December 4, 1990Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Kurt Burdeska
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Patent number: 4968781Abstract: A reactive dye of the formula ##STR1## in which Fa is the radical of an organic dye of the monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide series, T is a negative substituent, one X is a detachable substituent and the other X is a group of the formula ##STR2## A is arylene, V is hydrogen, a substituted or unsubstituted C.sub.1 -C.sub.4 alkyl radical or a radical of the formula --(CH.sub.2).sub.q --SO.sub.2 --Z, Z is a --CH.dbd.CH.sub.2 or CH.sub.2 --Y radical and Y is an inorganic or organic radical which is detachable under alkaline conditions, q, m and n are independently of one another an integral number from 2 to 6, R and R' are independently of one another hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl, and r is 1 or 2.Type: GrantFiled: March 28, 1988Date of Patent: November 6, 1990Assignee: Ciba-Geigy CorporationInventors: Karl Seitz, Karl Hoegerle
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Patent number: 4955987Abstract: The invention describes a process for the preparation of concentrated aqueous, substantially salt-free solutions of aminotriazinyl reactive dyes, which process comprises starting from a dye which contains sulfo groups and one or more radicals capable of reaction with cyanuric halide, said dye being at least partly in the form of the ammonium salt, reacting said dye with cyanuric halide, in the presence of lithium hydroxide, and deionizing and concentrating the salt-containing synthesis solution by a membrane separation process.The so prepared mixed lithium/ammonium salts of the acid aminotriazinyl reaction dyes are readily water soluble and are suitable for the preparation of concentrated storage stable dye solutions.Type: GrantFiled: December 6, 1985Date of Patent: September 11, 1990Assignee: Ciba-Geigy CorporationInventors: Roger Lacroix, Edmond Ruhlmann