The Alkylene, Alkenyl Or Alkenylene And The Ring Are Both Bonded Directly To The Same Sulfonyl Group Patents (Class 534/642)
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Patent number: 4841029Abstract: A disazo color having three triazine rings, one of which is substituted with a reactive group of --NR.sup.1 --A--SO.sub.2 C.sub.2 H.sub.4 OSO.sub.3 M, wherein R.sup.1 represents a hydrogen atom or a lower alkyl group; A represents a substituted or unsubstituted phenylene or naphthylene group; and M represents a hydrogen atom or an alkali metal. The disazo color is capable of dyeing cellulose-containing fibers under conditions conventionally employed for dyeing polyester fibers with a disperse dye, making it possible to dye mixed fibers of cellulose fiber and polyester fiber in a single-bath through one step.Type: GrantFiled: April 19, 1988Date of Patent: June 20, 1989Assignee: Mitsubishi Chemical Industries LimitedInventors: Yoshiaki Kato, Toshio Hihara
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Patent number: 4841033Abstract: A monoazo compound of the following formula in a free acid form, ##STR1## wherein R.sub.1 is alkyl, .beta.-carboxyethyl, .beta.-carboxyvinyl or phenyl, R.sub.2, R.sub.3 and R.sub.4 are each hydrogen or alkyl, A.sub.1 and A.sub.2 are each phenylene or naphthylene, B is ##STR2## in which R.sub.5 is hydrogen, methyl or sulfo, L is hydrogen or sulfo, and the asterisked linkage is bonded to the azo group, and Z.sub.1 and Z.sub.2 are each --SO.sub.2 CH.dbd.CH.sub.2, --SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H or the like, which is useful for dyeing or printing fiber materials to give dyed or printed products of extremely deep red color excellent in various fastness properties and dischargeability.Type: GrantFiled: September 29, 1987Date of Patent: June 20, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Toshihiko Morimitsu, Sadanobu Kikkawa, Naoki Harada, Takashi Omura
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Patent number: 4841031Abstract: A novel reactive monoazo dye, capable of giving cellulose fiber materials a deep orange to scarlet color and superior in build-up and chlorine fastness properties, represented by a free acid of the formula, ##STR1## wherein R.sub.1 is hydrogen, methyl or ethyl; R.sub.2 is an alkyl having 1 to 4 carbons that is either unsubstituted or substituted with hydroxy, cyano, alkoxy, halogen, carboxy, alkoxycarbonyl or sulfonic acid; Z is hydrogen or sulfonic acid; A is phenylene and is either unsubstituted or substituted with 1 or 2 substituents selected from the group consisting of methyl, ethyl, methoxy, ethoxy, chlorine, bromine and sulfonic acid, or natphthylene that is either unsubstituted or substituted with sulfonic acid; X is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Y in which Y is a group that is splittable by alkalis; and m is an integer of 1 to 3.Type: GrantFiled: September 7, 1984Date of Patent: June 20, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Yutaka Kayane, Katsumasa Otake, Yasuo Tezuka
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Patent number: 4839469Abstract: Dyestuffs of the formula ##STR1## wherein B=CH.dbd.CH.sub.2 or CH.sub.2 CH.sub.2 OSO.sub.3 H,u and v=H or SO.sub.3 H, with u=v,R=Cl, Br, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, COOH, SO.sub.3 H, NHCOCH.sub.3, SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 Hn=0, 1 or 2 ##STR2## These dyestuffs are outstandingly suitable for the dyeing and printing of materials containing hydroxyl groups or amide groups, such as cellulose, wool and polyamide, and give dyeings with good wet and light fastness properties.Type: GrantFiled: November 13, 1987Date of Patent: June 13, 1989Assignee: Bayer AktiengesellschaftInventor: Horst Jager
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Patent number: 4839468Abstract: Triazine compounds which in their betaine form correspond to the formula ##STR1## wherein Y denotes hydrogen or the radical of an azo dye-stuff,R denotes hydrogen or alkyl,Ar denotes arylene,Z denotes halogen, hydroxyl, alkoxy, alkyl, aryl or an amino group which may be monosubstituted or disubstituted,m denotes 0 or 1 andX.sup.(+) denotes an ammonium groupamd whereimthe cyclic and acyclic radicals can carry further substituents,are used for dyeing/coloring natural and synthetic substrates and compositions, in particular paper.Type: GrantFiled: November 13, 1984Date of Patent: June 13, 1989Assignee: Bayer AktiengesellschaftInventors: Horst Nickel, Peter Wild, Frank-Michael Stohr
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Patent number: 4837310Abstract: A monoazo compound of the following formula in a free acid form, ##STR1## wherein R.sub.1, R.sub.2 and R.sub.4 are independently hydrogen or lower alkyl, R.sub.3 is lower alkyl, acyl or (sulfo)- phenyl, R.sub.5 is hydrogen or sulfo, B is (sulfo)phenylene or sulfonaphthylmethylene, X is chlorine, fluorine, phenoxy or (substituted)amino, A is (substituted)phenylene or (substituted)naphthylene, and Z is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Y in which Y is a splittable group by the action of an alkali, which meets requirements of high degree in a dye industry with respect to dyeing properties such as build-up property and fastness properties such as formalin fastness, formalin-light fastness.Type: GrantFiled: January 9, 1987Date of Patent: June 6, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Toshihiko Morimitsu, Sadanobu Kikkawa, Takashi Omura
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Patent number: 4824942Abstract: A monoazo compound represented by the following formula in a free acid form, ##STR1## wherein A is phenylene unsubstituted or substituted with methyl, methoxy, chloro, carboxy or sulfo, or naphthylene unsubstituted or substituted with sulfo, R.sub.1 and R.sub.2 are independently hydrogen, chloro, methyl, nitro, carboxy or sulfo, excepting the case where both R.sub.1 and R.sub.2 are hydrogen, and X is --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 Y in which Y is a splittable group by the action of an alkali, which is useful for dyeing or printing fiber materials in a deep red color, and an aqueous liquid product of which is stable chemically and physically, even when stored for a long period of time.Type: GrantFiled: January 21, 1988Date of Patent: April 25, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Kazufumi Yokogawa, Noriaki Yamauchi, Takashi Omura
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Patent number: 4820806Abstract: Metal-free monoazo and disazo compounds of the formulaCH.sub.2 .dbd.CH--SO.sub.2 --W.sub.1 --D--N.dbd.N--K--(W.sub.2 --Z).sub.n,1:1 and 1:2 metal complexes of such metallizable metal-free compounds and acid addition salts of such metal-free compounds and 1:1 and 1:2 metal complexes, whereinD is the radical of a diazo component of the benzene, naphthalene or tetrahydronaphthalene series,K is the radical of a coupling component of the benzene, naphthalene, pyrazol-5-one, pyridine, pyridone, barbituric acid, quinoline, isoquinoline, benzeneazobenzene, benzeneazonaphthalene, naphthaleneazobenzene, naphthaleneazonaphthalene, tetrahydronaphthaleneazobenzene, tetrahydronaphthaleneazonaphthalene or acetoacetamide series,W.sub.1 is a direct bond or a divalent bridging radical,each W.sub.Type: GrantFiled: February 28, 1986Date of Patent: April 11, 1989Assignee: Sandoz, Ltd.Inventors: Werner Baumann, Joseph V. Diest, Herbert Eichenberger, Max Oppliger
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Patent number: 4818814Abstract: Water-soluble disazo compounds of the formula ##STR1## in which D is a benzene ring or a naphthalene ring which can both be substituted by substituents from the group consisting of chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, carboxy and sulfo, X is the vinyl group or a .beta.-sulfatoethyl group, R is a .beta.-sulfatoethylsulfonyl, 3-(.beta.-chloroethylsulfonyl)-benzoyl, 4-(.beta.-chloroethylsulfonyl)-benzoyl, 3-(.beta.-chloroethylsulfonylmethyl)-benzoyl, 4-(.beta.-chloroethylsulfonylmethyl)-benzoyl,4-(.beta.-chloroethylsulfonyl )-cinnamoyl, 3-(N-methyl-N-.beta.chloroethylsulfonyl)-aminobenzoyl or 4-(N-methyl-N-.beta.-chloroethylsulfonyl)-aminobenzoyl group, m is the number 1 or 2 and M denotes a hydrogen atom or an alkali metal.The disazo compounds are suitable for use as dyes having fiber-reactive properties for dyeing hydroxy- and/or carboxamido-containing fiber material, such as in particular cellulose fiber materials and polyamide fiber materials.Type: GrantFiled: October 14, 1986Date of Patent: April 4, 1989Assignee: Hoechst AktiengesellschaftInventor: Ludwig Schlafer
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Patent number: 4812558Abstract: A triazine compound having at least one symtriazine moiety of the following formula, ##STR1## wherein R is hydrogen or unsubstituted or substituted alkyl, Y is vinyl or --CH.sub.2 CH.sub.2 L in which L is a group splittable by the action of an alkali, and Z is phenylene or naphthylene unsubstituted or substituted once by sulfo, which is useful for dyeing or printing fiber materials to give dyed or printed products of excellent fastness properties with superior dye performance, even when dyebath conditions including temperatures, pH, amounts of an inorganic salt and bath ratio are varied to some extent.Type: GrantFiled: November 10, 1987Date of Patent: March 14, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Takashi Omura, Kazufumi Yokogawa
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Patent number: 4801693Abstract: Novel compounds of the general formula I ##STR1## where A is a fiber-reactive radical of the triazine, pyrimidine or vinylsulfone series, D is a radical of a sulfo-containing diazo component of the aniline or aminonaphthalene series, K is the radical of a coupling component of the aminohydroxynaphthalene series, X is fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, trifluoromethyl, C.sub.1 -C.sub.4 -alkoxy, phenoxy, hydroxysulfonyl, carboxyl, acetyl, propionyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, phenoxysulfonyl or unsubstituted or substituted carbamyl or sulfamyl, and Y is fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, trifluoromethyl, C.sub.1 -C.sub.4 -alkoxy, phenoxy, phenoxysulfonyl, acetyl, propionyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl, p-acetylaminophenylsulfonyl, hydroxysulfonyl, C.sub.1 -C.sub.Type: GrantFiled: August 20, 1987Date of Patent: January 31, 1989Assignee: BASF AktiengesellschaftInventors: Ortwin Schaffer, Manfred Patsch
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Patent number: 4798887Abstract: Novel compounds which, in the form of the free acid, are of the formula 1 ##STR1## where X is chlorine or fluorine and R is hydrogen, vinylsulfonylphenyl, .beta.-sulfatoethylsulfonylphenyl, vinylsulfonylbenzyl, sulfophenyl or .beta.-sulfatoethylsulfonylbenzyl, are particularly suitable for dyeing cotton.Type: GrantFiled: April 29, 1986Date of Patent: January 17, 1989Assignee: BASF AktiengesellschaftInventors: Heinz Krueger, Hartmut Lardon, Manfred Patsch
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Patent number: 4786721Abstract: The reactive dyes are useful, in particular, for dyeing or printing cellulose-containing fiber materials by the cold pad-batch method and produce, with a high dyeing yield, dyeings and prints having good fastness properties.Type: GrantFiled: August 13, 1986Date of Patent: November 22, 1988Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Peter Aeschlimann, Paul Herzig
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Patent number: 4782140Abstract: The invention relates to novel useful reactive dyes of the formula I ##STR1## in which: F is a radical selected from the group consisting of metal-free or metal-containing monoazo or disazo dyes containing at least one --SO.sub.3 H group, anthraquinone dyes, sulfophthalocyanine dyes, formazan dyes, phenazine dyes, oxanine dyes and nitroaryl dyes,R is hydrogen, C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted with --COOH or --SO.sub.3 H, cyanoethyl, or hydroxyethyl, X is fluorine, chlorine, bromine, --SO.sub.3 H, phenylsulfonyl or C.sub.1 -C.sub.4 -alkylsulfonyl,P is 1 or 2 andA is a radical of the formula ##STR2## in which: the groups designated "alk" are independently of each other straight or branched polymethylene radicals having 2 to 6 carbon atoms, andZ is .beta.-halogenoethyl, vinyl, .beta.-sulfatoethyl, .beta.-thiosulfatoethyl or .beta.acetoxyethyl.Type: GrantFiled: October 2, 1986Date of Patent: November 1, 1988Assignee: Ciba-Giegy CorporationInventor: Athanassios Tzikas
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Patent number: 4777247Abstract: A dyestuff which, in the form of its free acid, corresponds to the formula ##STR1## wherein W=a direct bond or a bridge member to a C atom of the naphthalene nucleus C or the benzene nucleus A, wherein the bridge member is ##STR2## wherein R=H or C.sub.1 -C.sub.4 -alkyl,alkylene=C.sub.2 -C.sub.5 -alkylene andarylene=unsubstituted or substituted phenylene,R.sub.1, R.sub.2 and R.sub.3 =H--, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, hydroxyl, halogen, carboxyl, sulphonamido, nitro, alkyl or arylcarbonylamino, --SO.sub.3 H, --SO.sub.2 --CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 --CH.sub.2 --Z,whereinZ=--OSO.sub.3 H, --SSO.sub.3 H, OPO.sub.3 H.sub.2, --OCOCH.sub.3, dialkylamino, or quaternary ammoniumR.sub.4 =H or C.sub.1 -C.sub.4 -alkyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkoxy, --OSO.sub.3 H, --SO.sub.3 H, --COOH or hydroxyl.X=a fibre-reactive radical,p=1 or 2,q=0 or 1,l, m and n=0 or 1,k=1 or 2 andMe=Cu.Type: GrantFiled: April 6, 1987Date of Patent: October 11, 1988Assignee: Bayer AktiengesellschaftInventor: Hermann Henk
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Patent number: 4775746Abstract: Water-soluble azo compounds having fiber-reactive dye properties conforming to the formula ##STR1## in which D denotes a benzene or naphthalene ring;R.sup.1 denotes hydrogen, alkyl, alkoxy, sulfo or carboxy;R.sup.Type: GrantFiled: September 30, 1986Date of Patent: October 4, 1988Assignee: Hoechst AktiengesellshaftInventors: Hartmut Springer, Michael Kunze, Marcos Segal, Werner H. Russ
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Patent number: 4769446Abstract: A water-soluble fiber-reactive red dyestuff is disclosed which, in its free acid form, has the formula ##STR1## wherein X is --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --Z wherein Z is --OH, --Cl, --Br, --OSO.sub.3 H, --SSO.sub.3 H, --OPO.sub.3 H.sub.2, --O.sub.2 CCH.sub.3, --O.sub.2 CCH.sub.2 CH.sub.3 or --N(lower alkyl).sub.2. Liquid compositions of said dyestuff are also disclosed. This dyestuff yields brilliant red shades on cellulosic materials having excellent fastness properties and superior color yield and build up.Type: GrantFiled: April 18, 1983Date of Patent: September 6, 1988Assignee: Hoechst Celanese CorporationInventors: Anthony J. Corso, Fritz Meininger, Thomas S. Phillips
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Patent number: 4766206Abstract: Disclosed are reactive dyes, and the use thereof, according to the formula(R--U).sub.n D--(X).sub.r,in which D is the radical of a monoazo, polyazo or metal complex azo dye; U is --CO-- or --SO.sub.2 --; R is a radical of the formula ##STR1## Z is sulfatoethyl, .beta.-thiosultafoethyl, .beta.-phosphatoethyl, .beta.-acetoxyethyl, .beta.-halogenoethyl or vinyl; alk is straight-chained or branched C.sub.1 -C.sub.6 -alkylene; Y is hydrogen, chlorine, bromine, fluorine, hydroxyl, sulfato, C.sub.1 -C.sub.4 -alkanoyloxy, cyano, carboxyl, alkoxycarbonyl having 1 to 5 C-atoms, carbamoyl or a radical --SO.sub.2 --Z in which Z is as defined above; V is hydrogen or C.sub.1 -C.sub.4 -alkyl unsubstituted or substituted by carboxyl, sulfo, C.sub.1 -C.sub.2 -alkoxy, halogen or hydroxyl or is a radical ##STR2## in which Z, alk and Y are as defined above; R.sub.1 is hydrogen or C.sub.1 -C.sub.6 -alkyl; alk' are independently of each other straight-chained or branched C.sub.2 -C.sub.Type: GrantFiled: September 24, 1986Date of Patent: August 23, 1988Assignee: Ciba-Geigy CorporationInventor: Athanassios Tzikas
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Patent number: 4762916Abstract: Water-soluble compounds having fiber-reactive dye properties of the general formula ##STR1## in which A is an alkylene of 2 to 6 carbon atoms or a phenylene which can be substituted by 1 or 2 substituents, or is a radical of the formula ##STR2## in which W is a direct bond or a bridge member and the R' and R* each denote hydrogen, chlorine, methyl, methoxy, ethoxy, carboxy or sulfo;B is chlorine or fluorine;R is hydrogen, chlorine, an alkyl of 1 to 4 carbon atoms or an alkoxy of 1 to 4 carbon atoms;M is hydrogen or an alkali metal;n stands for the number zero, 1 or 2,K is a radical of the formula ##STR3## in which D is phenylene which can be substituted by chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, carboxy or sulfo, or is naphthalene with optionally 1 or 2 sulfo groups,R.sup.1 denotes hydrogen, chlorine, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms,R.sup.Type: GrantFiled: December 23, 1986Date of Patent: August 9, 1988Assignee: Hoechst AktiengesellschaftInventors: Ludwig Schlafer, Hartmut Springer, Michael Kunze
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Patent number: 4757136Abstract: Water-soluble azo compounds having fiber-reactive dye properties conforming to the formula ##STR1## in which D denotes a benzene or naphthalene ring;R.sup.1 denotes hydrogen, alkyl, alkoxy, sulfo or carboxy;R.sup.Type: GrantFiled: September 30, 1986Date of Patent: July 12, 1988Assignee: Hoechst AktiengesellschaftInventors: Hartmut Springer, Michael Kunze, Marcos Segal, Werner H. Russ
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Patent number: 4754024Abstract: The invention relates to reactive dyes of the formula ##STR1## wherein D is the radical of a diazo component, R.sub.1 and R.sub.2 are each independently an unsubstituted or substituted alkyl or alkenyl group, Y is a --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --X radical in which X is a fibre-reactive radical, and the benzene ring A may be further substituted. These dyes are suitable for dyeing and printing textile fibre material and yield dyeings and prints of good fastness properties.Type: GrantFiled: August 25, 1986Date of Patent: June 28, 1988Inventor: Hansrudolf Schwander
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Patent number: 4754023Abstract: A reactive dye of the formula ##STR1## in which: F is a radical selected from the group consisting of metal-free or metal-containing monoazo or disazo dyes containing at least one --SO.sub.3 H group, anthraquinone dyes, sulfophthalocyanine dyes, formazan dyes, phenazine dyes, oxazine dyes and nitroaryl dyes,R is hydrogen, C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted with --COOH or --SO.sub.3 H, cyanoethyl, or hydroxyethyl,X is fluorine, chlorine, bromine, --SO.sub.3 H, phenylsulfonyl or C.sub.1 -C.sub.4 -alkylsulfonyl,p is 1 or 2 andA is a radical of the formula ##STR2## in which: Y is chlorine, bromine, fluorine, --OH, --OSO.sub.3 H, --O-acyl, --CN, --COOH, --COO--C.sub.1 -C.sub.4 -alkyl, --CONH.sub.2 or --SO.sub.2 --Z,the group designated "alk" is a straight or branched polymethylene radical having 2 to 6 carbon atoms,V is ##STR3## hydrogen or C.sub.1 -C.sub.4 -alkyl which is unsubstituted or substituted by C.sub.1 -C.sub.2 -alkoxy, carboxyl, sulfo, halogen or hydroxy,Z is .beta.Type: GrantFiled: January 23, 1986Date of Patent: June 28, 1988Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Herbert Seiler, Peter Scheibli
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Patent number: 4746323Abstract: This invention is directed to mixtures of water-soluble, fiber reactive yellow dyestuffs which exhibit superior build-up and color properties over those properties obtained with the individual components of the mixtures. The dyestuffs disclosed herein have the following general formula in their free acid form: ##STR1## wherein R is lower alkyl, lower alkoxy or hydrogen and wherein X is --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --Z wherein Z is --OH, --Cl, --Br, --OSO.sub.3 H, --SSO.sub.3 H, OPO.sub.3 H.sub.2 or --N(R.sub.1).sub.2, and wherein R.sub.1 is lower alkyl or hydrogen.Type: GrantFiled: August 24, 1987Date of Patent: May 24, 1988Assignee: Hoechst Celanese CorporationInventors: Thomas S. Phillips, Anthony J. Corso
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Patent number: 4746732Abstract: 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: July 30, 1984Date of Patent: May 24, 1988Assignee: Ciba-Geigy CorporationInventor: Athanassios Tzikas
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Patent number: 4740592Abstract: Water soluble azo compounds having fiber-reactive dye properties conforming to the formula ##STR1## in which D denotes a benzene or naphthalene ring;R.sup.1 denotes hydrogen, alkyl, alkoxy, sulfo or carboxy;R.sup.Type: GrantFiled: September 30, 1986Date of Patent: April 26, 1988Assignee: Hoechst AktiengesellschaftInventors: Hartmut Springer, Michael Kunze, Marcos Segal, Werner H. Russ
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Patent number: 4731441Abstract: Water-soluble monoazo and disazo compounds having fiber-reactive dye properties which are suitable for dyeing carbamoyl- and hydroxyl-containing materials, in particular cellulose fiber materials, and containing as diazo components an optionally substituted phenyl radical or naphthyl radical or a phenylazophenyl, phenylazonaphthyl, naphthylazophenyl or naphthylazonaphthyl radical, one of these radicals containing bonded in the diazo component a vinylsulfonyl, .beta.-thiosulfatoethylsulfonyl, .beta.-phosphatoethylsulfonyl, .beta.-chloroethylsulfonyl or .beta.-sulfatoethylsulfonyl group, and as coupling component that of a naphthol, aminonaphthaline or aminobenzene having a fiber-reactive grouping of the general formula ##STR1## in which the two R.sup.1 s, identical to or different from each other, denote a hydrogen atom or an optionally substituted alkyl group of 1 to 4 carbon atoms, R is a hydrogen atom or a sulfo group and Y represents the vinyl group, a .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.Type: GrantFiled: March 19, 1986Date of Patent: March 15, 1988Assignee: Hoechst AktiengesellschaftInventors: Marcos Segal, Michael Kunze
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Patent number: 4730038Abstract: Water-soluble disazo compounds having fiber-reactive dyestuff properties of the general formula (1) ##STR1## in which D.sub.1 and D.sub.2 are identical or different and each represents a phenyl radical or a naphthyl radical, both of which are substituted by a group of the formula moiety Y or formula moiety Z defined below and can additionally be substituted by one or two substituents from the group comprising sulfo, chlorine, bromine, lower alkyl and lower alkoxy, Z is a group of the formula (2a), (2b), (2c), (2d), (2e) or (2f) ##STR2## in which R denotes an alkyl group having 1 to 4 C atoms and X denotes a chlorine atom, the acetoxy group, the thiosulfate group, the phosphate group or the sulfato group; Y is a radical of the formula (3) ##STR3## in which R.sup.1 and R.sup.Type: GrantFiled: December 16, 1985Date of Patent: March 8, 1988Assignee: Hoechst AktiengesellschaftInventors: Fritz Meininger, Ernst Hoyer, Rudolf Fass
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Patent number: 4725675Abstract: Water-soluble azo compounds of the formula (1) ##STR1## in which R is hydrogen or alkyl of 1 to 4 carbon atoms, X is alkyl of 1 to 6 carbon atoms substituted by carboxy or sulfo, or is phenyl substituted by 1 or 2 sulfo or carboxy or both, and Z is vinyl, .beta.-thiosulfatoethyl or .beta.-sulfatoethyl and M is hydrogen or the equivalent of a metal, and in which the second sulfo group in the naphthalene is bonded in the m-position or p-position relative to the acylated amino group. The new azo compounds are very valuable dyestuffs having fiber-reactive properties, and give color-fast and deep dyeings and prints on fiber materials made of cellulose or synthetic or natural polyamide fibers.Type: GrantFiled: December 5, 1983Date of Patent: February 16, 1988Assignee: Hoechst AktiengesellschaftInventors: Fritz Meininger, Joachim Otten
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Patent number: 4725674Abstract: Water-soluble monoazo and disazo compounds which have fiber-reactive dyestuff properties and containing as diazo component an optionally substituted phenyl radical or naphthyl radical or an optionally substituted phenylazophenyl, phenylazonaphthyl, naphthylazophenyl or naphthylazonaphthyl radical, and as coupling component that of a naphthol, aminonaphthaline or aminobenzene and as fiber-reactive group a group of the formula ##STR1## in which both R.sup.1 s, identical to or different from one another, denote a hydrogen atom or an optionally substituted alkyl group of 1 to 4 carbon atoms, R is a hydrogen atom or a sulfo group and Y represents a vinyl group or a .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-chloroethyl or .beta.-sulfatoethyl group, this fiber-reactive grouping being bonded to the radical of the coupling component.Type: GrantFiled: March 19, 1986Date of Patent: February 16, 1988Assignee: Hoechst AktiengesellschaftInventors: Marcos Segal, Michael Kunze
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Patent number: 4707545Abstract: Lithium salts of anionic dyes are prepared by first converting another salt of this anionic dye in aqueous solution or suspension by means of a compound which releases calcium ions into the water-insoluble or sparingly water-soluble calcium salt of the dye, which is separated from the aqueous medium and is then converted to an aqueous suspension by treatment with lithium sulfate or lithium hydrogensulfate or a mixture thereof in an equivalent amount of each or in an excess of up to 10% into its lithium salt.Type: GrantFiled: November 26, 1985Date of Patent: November 17, 1987Assignee: Hoechst AktiengesellschaftInventors: Fritz Meininger, Ludwig Schlafer
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Patent number: 4703112Abstract: Water-soluble azo compounds, having fiber-reactive properties and yielding (for instance, on cellulose fiber materials) deep and fast dyeings and prints, of the formula ##STR1## in which D is phenylene which can be substituted by one or two subtituents from the group consisting of lower alkyl, lower alkoxy, hydroxy, lower alkanoylamino, benzoylamino, benzoylamino substituted by lower alkyl, lower alkoxy, chlorine and/or sulfo, chlorine, bromine, fluorine and carboxy and/or by a nitro group and/or by a further group of the formula Y--SO.sub.2 --(CH.sub.2).sub.Type: GrantFiled: October 30, 1986Date of Patent: October 27, 1987Assignee: Hoechst AktiengesellschaftInventors: Peter Mischke, Ludwig Schlafer
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Patent number: 4703111Abstract: Water-soluble monoazo and disazo compounds having fiber-reactive dye properties which are suitable for dyeing carboxamido and/or hydroxy-containing materials, in particular cellulose fiber materials, and contain as coupling component that of a naphthol, aminonaphthalene or aminobenzene and as diazo component an optionally chlorine-, alkyl-, alkoxy- and/or sulfo-substituted phenyl radical or an optionally substituted phenylazophenyl or phenylazonaphthyl radical having the fiber-reactive group of the general formula ##STR1## in which the two R.sup.1, identical to or different from each other, denote a hydrogen atom or an optionally substituted alkyl group of 1 to 4 carbon atoms, R is a hydrogen atom or a sulfo group and Y represents the vinyl group or a .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-chloroethyl or .beta.-sulfatoethyl group, as substituent, and a further such fiber-reactive grouping can be bonded to the radical of the coupling component.Type: GrantFiled: April 7, 1986Date of Patent: October 27, 1987Inventors: Marcos Segal, Michael Kunze
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Patent number: 4701524Abstract: A monoazo compound, or a salt thereof, of the formula, ##STR1## wherein W is a hydrogen atom or a carbamoyl group, R.sub.1 is a lower alkyl group, R.sub.2 and R.sub.3 are independently a hydrogen atom or a lower alkyl group, A is an unsubstituted or substituted phenylene or naphthylene group, Y is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z, in which Z is a group capable of being split by the action of an alkali, and X is an aromatic or aliphatic group substituted with one or two members selected from sulfonic acid group and carboxylic acid group, which is useful for dyeing fiber materials to give dyed products of a characteristic yellow color excellent in various fastness properties.Type: GrantFiled: November 5, 1985Date of Patent: October 20, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Yutaka Kayane, Hirokazu Sawamoto, Takashi Omura, Naoki Harada, Akira Takeshita
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Patent number: 4701523Abstract: Water-soluble disazo compounds which have fiber-reactive dye properties, which are suitable for dyeing carboxamido- and/or hydroxy- containing materials, in particular cellulose fiber materials, and which contain as bivalent coupling component 1-amino-8-naphthol-3,6- or -4,6-disulfonic acid and as diazo components an optionally substituted phenyl radical or naphthyl radical, one or both of the diazo components possessing a fiber-reactive group of the general formula ##STR1## in which the two R.sup.1, identical to or different from each other, denote a hydrogen atom or an optionally substituted alkyl group of 1 to 4 carbon atoms, R is a hydrogen atom of a sulfo group and Y represents the vinyl group or a .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-chloroethyl or .beta.-sulfatoethyl group, and it being possible for one of these diazo components also to contain, as substituent in place of this fiber-reactive grouping, a fiber-reactive group of the formula --SO.sub.Type: GrantFiled: May 13, 1986Date of Patent: October 20, 1987Inventors: Marcos Segal, Michael Kunze
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Patent number: 4698421Abstract: A compound, or a salt thereof, represented by the following formula, ##STR1## wherein A is a substituted or unsubstituted phenylene or naphthylene group, B is ##STR2## in which R.sub.3 is a hydrogen atom or a lower alkyl, lower alkoxy, acylamino or ureido group, and R.sub.4 is a hydrogen atom or a lower alkyl or lower alkoxy group, R.sub.1 and R.sub.3 are independently a hydrogen atom or a substituted or unsubstituted lower alkyl group, X is a substituted or unsubstituted amino, lower alkoxy, substituted phenoxy or sulfo group, Y is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z, in which Z is a group capable of being split by the action of an alkali, and m is 2 or 3, which is useful for dyeing hydroxyl group- or amide group-containing fiber materials to give dyed products of a brown color having excellent fastness properties with good build-up property.Type: GrantFiled: June 7, 1985Date of Patent: October 6, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Yutaka Kayane, Hirokazu Sawamoto, Takashi Omura, Naoki Harada
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Patent number: 4686286Abstract: A disazo reaction dyestuff for cellulose fibers which is of the formula: ##STR1## wherein D is a residue of a monoazo dye, R.sup.1 is hydrogen or lower alkyl, and X is a group: ##STR2## wherein R.sup.2 and R.sup.3 are each hydrogen, methyl, methoxy or --SO.sub.3 M, Y is an aromatic or aliphatic divalent residue and M is hydrogen or an alkali metal.Type: GrantFiled: May 17, 1985Date of Patent: August 11, 1987Assignee: Mitsubishi Chemical Industries LimitedInventors: Toshio Niwa, Yoshiaki Katoh
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Patent number: 4678851Abstract: Metal complex dyes that produce level, fast dyeings on textile materials are provided according to the formula ##STR1## wherein: D is a benzene, naphthalene or heterocyclic radical of a diazo component;Y is nitrogen or --CH;K is the radical of a coupling component if Y is nitrogen, or an o-hydroxyaldehyde radical if Y is --CH:Ka is a cation;Me is chromium or cobalt;Z.sub.1 is --O-- or --COO-- ortho to N.dbd.YZ.sub.2 is --O-- or --NR vicinal to N.dbd.Y, wherein R is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl or phenyl;X is a fiber reactive radical bound directly to or through an amino or amino-containing group to the complex;R.sub.1 is a direct bond or substituted or unsubstituted C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkenyl, or aryl radical or heterocyclic radical containing 1 to 3 sulfur, oxygen or nitrogen atoms;R.sub.2 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.8 -alkyl or aryl;R.sub.3 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.Type: GrantFiled: March 28, 1985Date of Patent: July 7, 1987Assignee: Ciba-Geigy CorporationInventors: Gerhard Back, Hans U. Schutz, Ulrich Schlesinger
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Patent number: 4667022Abstract: A red reactive dye represented by a free acid of the formula, ##STR1## wherein X is a hydrogen atom, a methyl, methoxy or sulfonic acid group, Y is --CH.dbd.CH.sub.2, --CH.sub.2 CH.sub.2 Y.sub.1 or --CH.sub.2 CH.sub.2 OY.sub.2 (in which Y.sub.1 is a halogen atom, and Y.sub.2 is the residue of polybasic acids), R is a C.sub.1 -C.sub.4 alkyl group, R.sub.1 and R.sub.2 are each a hydrogen atom, a methyl or ethyl group, and the azo group is located on a meta-or para-position of the benzene ring A with respect to the --NR.sub.2 -- group and the sulfonic acid group on the benzene ring A is adjacent to the azo group. This dye is suitable for dyeingcellulose fibers red to afford dyeings superior in fastnesses, acid stability, build-up property, level dyeing property and white dischargeability.Type: GrantFiled: February 13, 1981Date of Patent: May 19, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Toshio Nakamatsu, Yoshikazu Matsuo, Yasuo Tezuka
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Patent number: 4663440Abstract: A brown reactive dye represented by a free acid of the formula, ##STR1## wherein R is a hydrogen atom or a C.sub.1 to C.sub.4 alkyl group, X is --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 or --SO.sub.2 CH.sub.2 CH.sub.2 OPO.sub.3 H.sub.2, rings A, B and C are each a benzene or naphthalene ring which may have other substituent, m is 0 to 3 and n is 0 to 1.This dye is suitable for dyeing cellulose fibers brown to afford dyeings superior in fastnesses, acid stability, build-up property and level dyeing property.Type: GrantFiled: May 26, 1981Date of Patent: May 5, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Takashi Omura, Masaki Sunami, Yasuo Tezuka
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Patent number: 4659807Abstract: Monoazo compounds which are suitable as fiber-reactive dyestuffs have the general formula (1) ##STR1## in which: D is a benzene or naphthalene ring or a radical of the formula (2) or (3) ##STR2## R.sup.1 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, hydroxy, nitro or halogen, if D stands for a benzene ring, andR.sup.2 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, carboxy or sulfo, if D stands for a benzene ring, orR.sup.1 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, carboxy, halogen, sulfo or a group of the formula --SO.sub.2 --Y (where Y has the meaning mentioned hereinafter), if D stands for a naphthalene ring, andR.sup.2 is hydrogen or sulfo, if D is a naphthalene ring, orR.sup.1 is, if D is a radical of the formula (2), hydrogen, nitro, chlorine or alkoxy of 1 to 4 carbon atoms, R.sup.1 being bonded to the benzene nucleus V, andR.sup.Type: GrantFiled: July 22, 1985Date of Patent: April 21, 1987Assignee: Hoechst AktiengesellschaftInventor: Marcos Segal
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Patent number: 4652634Abstract: A water-soluble azo compund of formula ##STR1## in which Y is vinyl or --CH.sub.2 --CH.sub.2 --Z in which Z is chlorine, bromine, fluorine, lower alkanoyloxy, benzoyloxy, sulfobenzoyloxy, benzenesulfonyloxy, toluenesulfonyloxy, lower alkylsulfonylamino, arylsulfonylamino, phenoxy, dialkylamino, each alkyl being of from 1 to 4 carbon atoms, thiosulfato, phosphato or sulfato;n is the number zero or 1;D is phenylene unsubstituted or substituted by one or two substituents selected from the group consisting of lower alkyl, lower alkoxy, hydroxy, lower alkanoylamino, chlorine, bromine, fluorine and carboxy; by one nitro substituent; by one sulfo substituent; by one substituent of the formula Y--SO.sub.2 --(CH.sub.2).sub.n -- in which n is 1; by a plurality of substituents selected from the group consisting of said one or two substituents, said one nitro substituent, said one sulfo substituent and said one substituent of the formula Y--SO.sub.2 --(CH.sub.2).sub.Type: GrantFiled: January 15, 1986Date of Patent: March 24, 1987Assignee: Hoechst AktiengesellschaftInventors: Peter Mischke, Hermann Fuchs
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Patent number: 4649193Abstract: Water-soluble fibre-reactive dyestuffs containing one or two fibre-reactive groups of the vinylsulfone series and one or two fibre-reactive groups of the fluoro-s-triazinyl-amino series. These dyestuffs can be applied on fibre materials containing hydroxy and/or carbonamide groups by known application and fixation techniques for fibre-reactive dyes to yield deep and fast dyeings on these materials.Type: GrantFiled: August 1, 1983Date of Patent: March 10, 1987Assignee: Hoechst AktiengesellschaftInventors: Fritz Meininger, Joachim W. Otten, deceased, by Ursula Otten, heir, by Anna G. Rudolph nee Otten, heir
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Patent number: 4645832Abstract: Reactive azo dyes represented by the general formula (I) or (II): ##STR1## wherein M is a hydrogen atom or an alkali metal, R.sup.1 is a hydrogen atom, a chlorine atom, a lower alkyl group, a lower alkoxy group, a nitro group or a carboxyl group, R.sup.2 and R.sup.8 are a lower alkyl group, a lower alkoxy group or a sulfonic acid group, R.sup.3, R.sup.7 and R.sup.9 are a hydrogen atom, a lower alkyl group, a lower alkoxy group, an acetylamino group or a sulfonic acid group, R.sup.4 and R.sup.5 are a hydrogen atom, a methyl group, a methoxy group or a sulfonic acid group, R.sup.6 is a hydrogen atom, a lower alkyl group, a lower alkoxy group or a sulfonic acid group, Z.sup.1 is a chlorine atom, a fluorine atom, an aliphatic or an aromatic amino residual group, a methoxy group or a phenoxy group, Z.sup.2 is the same one as Z.sup.1 when Z.sup.3 is ##STR2## Z.sup.2 is a chlorine atom or a fluorine atom when Z.sup.Type: GrantFiled: April 9, 1985Date of Patent: February 24, 1987Assignee: Mitsubishi Chemical Industries LimitedInventors: Toshio Niwa, Yoshiaki Kato
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Patent number: 4644058Abstract: A monoazo compound represented by a free acid of the formula: ##STR1## wherein R.sub.1 and R.sub.2 independently represent a hydrogen atom, or an alkyl, aralkyl or cyclohexyl group; R.sub.3 represents a hydrogen atom or a methyl or sulfonic acid group; R.sub.4 represents a hydrogen atom or an alkyl group; A represents an oxygen atom or --NH--; X.sub.1 and X.sub.2 independently represent a hydrogen or chlorine atom, or a methyl, methoxy, carboxyl or sulfonic acid group; and Y represents --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 Z in which Z represents a halogen atom, --OSO.sub.3 H or --OPO.sub.3 H.sub.2. This compound is used for dyeing cellulose fibers to give dyed products of yellow to reddish yellow having excellent fastnesses, particularly chlorine fastness.Type: GrantFiled: November 18, 1982Date of Patent: February 17, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Yasutaka Shimidzu, Naoki Harada, Yasuo Tezuka
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Patent number: 4638054Abstract: The invention provides new reaction dyestuffs of the formula ##STR1## where n and m are each 0 or 1 such that n+m=1 or 2 and whereG is a radical of the formula ##STR2## wherein B is a direct bond between D or D' and X or represents a bridge member as described in the specification,X is S, SO or SO.sub.2,Y is optionally substituted alkylene,R is H, optionally substituted C.sub.1 -C.sub.4 -alkyl or optionally substituted C.sub.2 -C.sub.4 -alkylene or optionally substituted phenylalkylene,Z is a fibre-reactive radical, and whereD and D' are as defined in the body of the Application.On hydroxyl- or amide-containing textile materials the new reactive dyestuffs produce prints and dyeings of a high fastness level.Type: GrantFiled: October 18, 1984Date of Patent: January 20, 1987Assignee: Bayer AktiengesellschaftInventors: Karl J. Herd, Martin Michna
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Patent number: 4626589Abstract: A compound of the formula, ##STR1## wherein D is an organic dye moiety, R.sub.1 and R.sub.2 are independently hydrogen or a substituted or unsubstituted lower alkyl group, R.sub.3 is hydrogen or a substituted or unsubstituted lower alkyl, phenyl or naphthyl group, X.sub.1 and X.sub.2 are independently hydrogen, halogen or a lower alkyl, cyano, carbamoyl, vinyl, .beta.-hydroxyethyl, .beta.-sulfoethyl, .beta.-sulfatoethyl, carboxyl, carboxylic acid ester or sulfonic acid group, and Z is appended to the above-defined D or R.sub.3 and stands for --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Y, in which Y is a group capable of being split by the action of an alkali, which is useful for dyeing hydroxyl or amido group-containing fiber materials with excellent build-up properties, thereby giving dyed products having excellent various fastness properties.Type: GrantFiled: February 7, 1985Date of Patent: December 2, 1986Assignee: Sumitomo Chemical Company, LimitedInventors: Takashi Omura, Yutaka Kayane, Mikoto Takahashi, Tetsuya Miyamoto, Akira Takeshita, Naoki Harada, Katsumasa Otake
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Patent number: 4622390Abstract: Water-soluble disazo dyestuffs of the formula ##STR1## which contain a 1-amino-8-naphthol-3,6- or -4,6-disulfonic acid moiety as a bivalent coupling component and which contain diazo components with fibre-reactive groups characterized by the inclusion of one or two chloro-triazinyl groups and one or two of the six groups defined by the substituent Z, namely, ##STR2## each of which are connected to the benzene moiety of the diazo component; the chloro-triazinyl group is further substituted by a substituted or unsubstituted phenylamino or substituted or unsubstituted naphthylamino group, a substitutent of which may be one of the six groups defined by the Z substituent; if there is only one chloro-triazinyl group in the compound, then the diazo component is also substituted by one of the Z substituents; these compounds are dyestuffs which exhibit a good fixation degree of the dyestuffs in fabrics.Type: GrantFiled: September 9, 1985Date of Patent: November 11, 1986Assignee: Hoechst AktiengesellschaftInventors: Fritz Meininger, Ernst Hoyer, Joachim W. Otten, deceased, by Ursula Otten, heir, by Anna G. Rudolph nee Otten, heir, Rudolf Fass
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Patent number: 4602084Abstract: Monoazo dyes of the formula ##STR1## in which K is the radical of a coupling component of the benzene or naphthalene series or of the heterocyclic series, and R is a ##STR2## --CO--R.sub.2 or --SO.sub.2 --O--R.sub.2 group in which R.sub.1 is hydrogen or C.sub.1-4 -alkyl and R.sub.2 is a substituted or unsubstituted monosulfo-C.sub.1-12 -alkyl radical, a substituted or unsubstituted monosulfophenyl, disulfophenyl, monosulfonaphthyl or disulfonaphthyl radical, and X and Y, independently of each other, are hydrogen, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, halogen, C.sub.2-6 -alkanoylamino, C.sub.1-5 -alkylsulfonylamino or a substituted or unsubstituted phenyl or phenoxy radical, produce dyeings on polyamide material which have good light and wet fastness properties.Type: GrantFiled: July 8, 1983Date of Patent: July 22, 1986Assignee: Ciba-Geigy CorporationInventor: Rudolf Hurter
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Patent number: 4585460Abstract: Reactive dyes of the formula ##STR1## wherein Y is a --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --X radical, in which X is a leaving group, and Z is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or carboxy, and K is the radical of a coupling component which couples at pH.ltoreq.7, are suitable for dyeing and printing textile fibre material and give dyeings and prints of good fastness properties.Type: GrantFiled: September 30, 1983Date of Patent: April 29, 1986Assignee: Ciba-Geigy CorporationInventors: Hansrudolf Schwander, Jurgen Markert, Peter Aeschlimann
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Patent number: 4564672Abstract: New water-soluble azo compounds which have the general formula (1) ##STR1## in which K is the radical of a water-soluble coupling component which can couple at one or two positions in the molecule and which belongs to the series comprising aminobenzenes, phenols, naphthols, aminonaphthols, acylaminonaphthols, dihydroxynaphthalenesulfonic acids, phenylazoaminonaphtholsulfonic and naphthylazoaminonaphtholsulfonic acids, 5-pyrazolones and 5-aminopyrazoles and 2-hydroxy-6-pyridones, R represents an alkoxy group of 1 to 4 C-atoms and X a group of the formula --SO.sub.2 --CH.dbd.CH.sub.2 or --SO.sub.2 --CH.sub.2 --CH.sub.2 --Z in which Z is a group which can be eliminated under alkaline conditions, furthermore, the copper complex compounds of the above-mentioned metal-free compounds of the general formula (1).Type: GrantFiled: July 27, 1983Date of Patent: January 14, 1986Assignee: Hoechst AktiengesellschaftInventor: Ludwig Schlafer