The Hetero Ring And Benzene Ring, To Which An Azo Group Is Bonded Directly, Bonded Directly To The Same Nitrogen Patents (Class 534/638)
  • Patent number: 4952679
    Abstract: Reactive dyes suitable for dyeing and printing cellulosic fiber materials by the cold pad-batch process having the formula ##STR1## wherein Fa is a monoazo or polyazo, metal complex azo, anthraquinone, phthalocyanine, formazane, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye radical, X.sub.1 is halogen, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl, a sulfonic acid or phosphoric acid group or a quaternized ammonium group, X.sub.2 independently has the meaning of X.sub.1 or is C.sub.1 -C.sub.4 -alkyl which is unsubstituted or substituted by halogen, hydroxy, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl or C.sub.1 -C.sub.4 alkoxy, R is hydrogen or C.sub.1 -C.sub.4 -alkyl which is unsubstituted or substituted by halogen, hydroxy, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl or C.sub.1 -C.sub.4 -alkoxy, and r is 1 or 2.
    Type: Grant
    Filed: August 19, 1988
    Date of Patent: August 28, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Karl Hoegerle
  • Patent number: 4948879
    Abstract: Monoazo compounds conforming to the general formula (1) shown and defined hereinafter have very good fiber-reactive dye properties and dye hydroxy- and/or carboxamido-containing material, in particular fiber material, such as wool and in particular cellulose fibers, in strong fast shades. ##STR1## where the symbols have the following meanings: D is a benzene or naphthalene ring or a heterocyclic radical,R.sup.1 and R.sup.
    Type: Grant
    Filed: November 17, 1988
    Date of Patent: August 14, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Horst Tappe, Dieter Oehme, Werner H. Russ
  • Patent number: 4946947
    Abstract: Water-soluble azo compounds of the general formula D-N=N-K in which D is a radical of the general formula ##STR1## in which Y denotes the vinyl group or is an ethyl group which is substituted in the .beta.-position by a substituent which can be eliminated by means of alkali, R stands for hydrogen, hydroxy, lower alkyl, lower alkoxy, carboxy or halogen, n is the number zero or 1, M is hydrogen or a salt-forming metal atom, and the free bond from the benzene ring to the azo groups is in the meta- or para-position to the nitrogen atom of the benzotriazole radical, and in which K is a radical of a water-soluble coupling component, such as, for example, from the series comprising the aminobenzenes, phenols, naphthols, aminonaphthols, acylaminonaphthols, pyrazolones, aminopyrazoles, acetoacetylarylides and hydroxypyridones.
    Type: Grant
    Filed: June 5, 1989
    Date of Patent: August 7, 1990
    Inventors: Hartmut Springer, Kurt Hussong
  • Patent number: 4937326
    Abstract: A novel reactive monoazo dye, which can give to cellulose fiber materials a deep orange to scarlet color superior in build-up property and chlorine fastness, represented by a free acid of the formula, ##STR1## wherein D is a phenyl group substituted with 1 to 3 substitutes selected from methyl, ethyl, methoxy, ethoxy, halogen, acetylamino, propionylamino, benzoylamino, succinylamino, maleinylamino, nitro, suflonic acid and carboxyl groups; R.sub.1 is a hydrogen atom, or a methyl or ethyl group; R.sub.2 is an alkyl group having 1 to 4 carbon atoms which is unsubstituted or substituted with a hydroxy, cyano, alkoxy, halogen, carboxy, alkoxycarbonyl or sulfonic acid group; Z is a hydrogen atom or a sulfonic acid group; A is a phenylene residue which is unsubstituted or substituted with 1 or 2 substituents selected from methyl, ethyl, methoxy, ethoxy, chlorine, bromine and sulfonic acid groups; or a naphthylene residue which is unsubstituted or substituted with one sulfonic acid group; and X is --SO.sub.2 CH.dbd.
    Type: Grant
    Filed: March 22, 1985
    Date of Patent: June 26, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yutaka Kayane, Masaki Sunami, Katsumasa Otake, Yasuo Tezuka
  • Patent number: 4935501
    Abstract: Reactive dyes of the formula ##STR1## in which D is the radical of a dye of the monoazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide 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: Grant
    Filed: March 7, 1988
    Date of Patent: June 19, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanassios Tzikas
  • Patent number: 4929719
    Abstract: Reactive dyes which are particularly suitable for dyeing and printing cellulose containing fiber materials by the cold padbatch process and which produce, in high dye yield, dyeings and prints having good fastness properties containing the radical of an amine of the formula ##STR1## in which R is hydrogen, halogen, hydroxyl or sulfo, Z is a radical of the formula --CH.dbd.CH.sub.2 or --CH.sub.2 --CH.sub.2 --Y, Y is a detachable group, R' is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by --COOH, --CN, --OH or --SO.sub.3 H, and E is a radical of the formula ##STR2## in which R' and Z are as defined above, alk, alk' and alk" independently of one another are a C.sub.1 -C.sub.6 alkylene radical, U is hydrogen, halogen, hydroxyl, sulfato, C.sub.1 -C.sub.4 alkanoyloxy, cyano, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, carbamoyl or a radical --SO.sub.2 --Z in which Z is as defined above, V is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.
    Type: Grant
    Filed: August 10, 1989
    Date of Patent: May 29, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Hansrudolf Schwander, Athanassios Tzikas, Peter Aeschlimann
  • Patent number: 4917705
    Abstract: The invention relates to a process for dyeing or printing natural or synthetic polyamide fiber materials which comprises dyeing or printing these fiber materials with reactive dyes of the formula ##STR1## where each M is a cation, R.sub.1 and R.sub.2 are independently of each other hydrogen or C.sub.1 -alkyl, and X.sub.1 and X.sub.2 are independently of each other .alpha.,.beta.-dibromopropionyl, .alpha.-bromoacryloyl, chloroacetyl or a mono-, di- or trihalopyrimidinyl radical.
    Type: Grant
    Filed: September 21, 1988
    Date of Patent: April 17, 1990
    Assignee: Ciba-Geigy Corp.
    Inventors: Dieter Mausezahl, Peter Loew
  • Patent number: 4918183
    Abstract: The invention relates to monoazo dyes of the formula ##STR1## wherein K is the radical of a coupling component of the benzene, naphthalene or heterocyclic series, and R is hydrogen, halogen, carboxy, a C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.2 -C.sub.6 alkanoylamino, C.sub.1 -C.sub.6 alkylsulfonylamino, C.sub.1 -C.sub.6 alkylsulfonyl, phenyl(C.sub.1 -C.sub.4)alkylsulfonyl or naphthyl(C.sub.1 -C.sub.4)alkylsulfonyl or benzoyl radical, which radicals may be further substituted, or is a ##STR2## group, wherein each of R.sub.1 and R.sub.2 independently of the other is hydrogen or a C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or naphthyl radical, which radicals may be further substituted, and wherein X is hydrogen, halogen or a C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.2 -C.sub.6 alkanoylamino or C.sub.1 -C.sub.6 alkylsulfonylamino radical, which radicals may be further substituted.These dyes give dyeings of good light- and wetfastness properties on polyamide material.
    Type: Grant
    Filed: October 24, 1985
    Date of Patent: April 17, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Hurter
  • Patent number: 4918169
    Abstract: Reactive dyes suitable for dyeing and printing cellulosic fiber materials by the cold pad-batch process having the formula ##STR1## wherein Fa is a monoazo or polyazo, metal complex azo, anthraquinone, phthalocyanine, formazane, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, napthoquinone, pyrenequinone or perylene-tetracarbimide dye radical, X is halogen, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl, a sulfonic acid or phosphonic acid group or a quaternized ammonium group, r is 1 or 2, R is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy or phenyl, and A is a radical of the formula ##STR2## wherein R' is hydrogen, C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy or phenyl, C.sub.5 -C.sub.
    Type: Grant
    Filed: August 19, 1988
    Date of Patent: April 17, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Karl Hoegerle
  • Patent number: 4912244
    Abstract: Intermediate useful for the preparation of fiber-reactive dyes having the formula ##STR1## in which the alks independently of each other are C.sub.2 -C.sub.6 -alkylene and Z is .beta.-halogenoethyl, vinyl, .beta.-sulfatoethyl, .beta.-thiosulfatoethyl or .beta.-acetoxyethyl.
    Type: Grant
    Filed: July 19, 1988
    Date of Patent: March 27, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanassios Tzikas
  • Patent number: 4910298
    Abstract: A monoazo compound of the following formula, ##STR1## wherein D is sulfonaphthyl, sulfophenyl or carboxyphenyl, any one of A.sub.1 and A.sub.2 is sulfo and the other is hydrogen, methoxy or ethoxy, R.sub.1 and R.sub.2 are independently hydrogen or alkyl, B.sub.1 and B.sub.2 are independently phenylene or naphthylene, and Y.sub.1 and Y.sub.2 are independently vinyl, .beta.-sulfatoethyl or the like, which is useful for dyeing or printing fiber materials to give dyed or printed products of a deep color excellent in fastness properties.
    Type: Grant
    Filed: November 3, 1987
    Date of Patent: March 20, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazufumi Yokogawa, Sadanobu Kikkawa, Naoki Harada, Takashi Omura
  • Patent number: 4908436
    Abstract: A reactive dye of the formula ##STR1## or of the formula ##STR2## or of the formula ##STR3## in which D, D.sub.1 and D.sub.2 are each phenylene or naphthylene unsubstituted or substituted by alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, carboxylic acylamino having 1 to 8 carbon atoms, amino, alkylamino having 1 to 4 carbon atoms, phenylamino, N,N-di-.beta.-hydroxyethylamino, N,N-di-.beta.-sulfatoethylamino, sulfobenzylamino, N,N-disulfobenzylamino, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy radical, alkylsulfonyl having 1 to 4 carbon atoms, trifluoromethyl, nitro, cyano, halogen, carbamoyl, N-alkylcarbamoyl having 1 to 4 carbon atoms in the alkyl radical, sulfamoyl N-alkylsulfamoyl having 1 to 4 carbon atoms, N-(.beta.-hydroxyethyl)-sulfamoyl, N,N-di-(.beta.-hydroxyethyl)-sulfamoyl, N-phenylsulfamoyl, ureido hydroxyl, carboxyl, sulfomethyl, or sulfo, R.sub.1 is hydrogen or C.sub.1-4 -alkyl unsubstituted or substituted by halogen, hydroxyl, cyano, C.sub.
    Type: Grant
    Filed: October 23, 1986
    Date of Patent: March 13, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Scheibli
  • Patent number: 4906737
    Abstract: Fibre-reactive dyes of the formula ##STR1## wherein X is an alkyl or alkoxy group of 1 to 4 carbon atoms, a carboxy group or a halogen atom, each of R.sub.1 and R.sub.2 is independently a hydrogen atom or an alkyl group of 1 to 4 carbon atoms and D is the radical of an organic dye which contains sulpho groups, and the benzene ring A can contain further substituents apart from X and SO.sub.3 H.
    Type: Grant
    Filed: August 17, 1988
    Date of Patent: March 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Herbert Seiler, Gert Hegar, Ester Hegar-Zimmerman
  • Patent number: 4906739
    Abstract: A fibre-reactive azo dyestuff of the formula ##STR1## in which X is alkyl or alkoxy with 1 to 4 carbon atoms, carboxyl or halogen, n is 1, 2 or 3, m is 0 or 1, p is 0 or 1 and q is 0 or 1 and the benzene or naphthalene rings A, B and B' can contain further substituents in addition to SO.sub.3 H groups. The dyestuffs of the invention are suitable inter alia, for dyeing and printing silk, leather, wool, high molecular weight polyamide fibres and high molecular weight polyurethanes, but especially cellulose-containing materials having a fibrous structure.
    Type: Grant
    Filed: June 15, 1989
    Date of Patent: March 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Herbert Seiler, Gert Hegar
  • Patent number: 4904766
    Abstract: A monoazo compound represented by the following formula in a free acid form, ##STR1## wherein D is a sulfophenyl or sulfonaphthyl, R.sub.1, R.sub.2 and R.sub.3 are independently hydrogen or alkyl; B.sub.1 and B.sub.2 are independently phenylene, naphthylene, or alkylene, provided that at least one of B.sub.1 and B.sub.2 is phenylene or naphthylene, Y.sub.1 and Y.sub.2 are independently vinyl or --CH.sub.2 CH.sub.2 Z in which Z is splittable by the action of an alkali, and n is 0 or 1, and the monoazo compound is useful for dyeing or printing fiber materials to obtain dyed or printed products of extremely deep scarlet color excellent in various fastness with superior build-up property.
    Type: Grant
    Filed: October 13, 1987
    Date of Patent: February 27, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazufumi Yokogawa, Toshihiko Morimitsu, Naoki Harada, Takashi Omura, Sadanobu Kikkawa
  • Patent number: 4902786
    Abstract: 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: Grant
    Filed: May 20, 1988
    Date of Patent: February 20, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Springer, Michael Kunze, Marcos Segal
  • Patent number: 4897469
    Abstract: Azo reactive dyes of the aniline series for dye or printing fiber materials of the formula ##STR1## wherein K is the radical of a coupling component, and Z is a vinyl sulfonyl reactive group ortho- or para- to the azo bridge.
    Type: Grant
    Filed: April 1, 1988
    Date of Patent: January 30, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Eilingsfeld, Ruediger Iden
  • Patent number: 4879372
    Abstract: A triazine compound having a dye moiety, a sym-monohalotriazine moiety and an aminobenzoylamine moiety, which is represented, for example, by the following formula, ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are independently hydrogen or alkyl, A is phenylene or naphthylene, D is a dye moiety, X is chloro or fluoro, Z is --SO.sub.2 CH.dbd.CH.sub.2, --SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H or the like, and n is 0, 1 or 2, and which is useful for dyeing or printing fiber materials such as cellulose fiber materials with superior dye performance such as build-up property to give dyed or printed products excellent is fastness properties.
    Type: Grant
    Filed: November 6, 1987
    Date of Patent: November 7, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshihiko Morimitsu, Naoki Harada, Takashi Omura
  • Patent number: 4875903
    Abstract: Compounds of the formula ##STR1## wherein each R.sub.1 is independently hydrogen, C.sub.1-4 alkyl or C.sub.1-4 alkyl monosubstituted by hydroxy, halo, cyano or C.sub.1-4 alkoxy,each of X.sub.1 and X.sub.3 is independently halo, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenyl, phenoxy, amino or an aliphatic, cycloaliphatic, aromatic or heterocyclic amino group,each of X.sub.2 and X.sub.4 is independently an aliphatic, cycloaliphatic, aromatic or heterocyclic amino group containing at least one protonatable nitrogen atom or quaternary ammonium group,m is 0 or 1, andeach of n.sub.1 and n.sub.2 is independently 0 or 1, with the proviso that n.sub.1 +n.sub.2 is 1 or 2,wherein each halo is independently fluoro, chloro or bromo, with the provisos that (1) the total number of basic and cationic groups present as X.sub.1 -X.sub.
    Type: Grant
    Filed: June 5, 1987
    Date of Patent: October 24, 1989
    Assignee: Sandoz Ltd.
    Inventor: Reinhard Pedrazzi
  • Patent number: 4876334
    Abstract: Reactive dyes of the formula ##STR1## 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, B.sub.1 and B.sub.2 are independently of each other hydrogen or alkyl which has 1 to 4 carbon atoms and which can be substituted by halogen, hydroxyl, cyano, C.sub.1-4 alkoxy, C.sub.1-4 alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato, X is fluorine, chlorine, bromine, sulfo, alkylsulfonyl having 1 to 4 C atoms or phenylsulfonyl, B is a --CH.sub.2 --.sub.n or --O--CH.sub.2 --.sub.n radical, n is 1 to 6, R is a radical of the formula ##STR2## Z is .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-acyloxyethyl, .beta.
    Type: Grant
    Filed: February 1, 1988
    Date of Patent: October 24, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Paul Herzig
  • Patent number: 4873320
    Abstract: Water-soluble dyes which contain one or two fiber-reactive groups of the formula ##STR1## in which each R is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, it being possible for both R to have a meaning which is identical to or different from one another, Y is the vinyl group or a group of the general formula --CH.sub.2 --CH.sub.2 --X in which X represents a substituent which can be eliminated as an anion, and m represents the number 2 or 3. These novel dyes can be used to dye hydroxy and/or carboxamide group-containing materials in particular fiber-materials, such as, in particular, cellulose fiber materials, in fast shades.
    Type: Grant
    Filed: December 15, 1987
    Date of Patent: October 10, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Springer, Manfred Kuhn, Holger M. Buch
  • Patent number: 4866162
    Abstract: Azo dyes of the formula ##STR1## wherein D is a disulfonaphthyl-(2) residue, K is a naphtalene or benzene residue, R is hydrogen, and X is hydrogen, are especially suitable for dyeing of cellulosic materials of fibrous structure, they have a good exhaustion capacity and excellent dye fixation.
    Type: Grant
    Filed: October 2, 1986
    Date of Patent: September 12, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Herbert Seiler, Gert Hegar
  • Patent number: 4866163
    Abstract: Compounds of the formula ##STR1## wherein each R.sub.1 is independently hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or --NHCOC.sub.1-4 alkyl, each R.sub.2 is H, halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, each R.sub.3 is independently halo, hydroxy, C.sub.1-4 alkoxy, --NHOH, amino or an aliphatic, aromatic cycloaliphatic or saturated heterocyclic amino radical, and is divalent aliphatic or aromatic group or, together with the NH radicals to which it is attached, forms a piperazine ring, and the use thereof for dyeing or printing hydroxy group- or nitrogen-containing organic substrates after which the dyed or printed substrate is optionally treated with a cationic fixing agent.
    Type: Grant
    Filed: May 2, 1984
    Date of Patent: September 12, 1989
    Assignee: Sandoz, Ltd.
    Inventor: Werner Koch
  • Patent number: 4855410
    Abstract: The invention relates to a process for the preparation of azo compounds of the formula ##STR1## wherein K is the radical of a coupling component, R is a water-solubilising group and X is a fibre-reactive radical, and the benzene ring A may be further substituted, which process comprises reacting a compound of the formula ##STR2## in an aqueous medium containing 5 to 25% by weight of an alkali metal halide or alkali metal sulfate, based on the weight of the medium, with a compound which introduces the radical X to give the compound of the formula ##STR3## diazotising said compound direct and coupling the diazotisation product with a coupling component of the formulaH--K (4)in which formulae (2), (3) and (4) A, R, X and K are as defined for formula (1).
    Type: Grant
    Filed: July 9, 1986
    Date of Patent: August 8, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Rudiger Oxenius, Charles Wilhelm
  • Patent number: 4843149
    Abstract: A monoazo compound, or a salt thereof, represented by the formula, ##STR1## wherein D is a sulfophenyl group substituted with a methyl, ethyl, methoxy, ethoxy, phenoxy, acetylamino, pripionylamino, benzoylamino, carboxybenzoylamino, maleinylamino or succinylamino group, a naphthyl group substituted with two or three sulfo groups of a group of the formula ##STR2## any one of X.sub.1 or X.sub.2 is a sulfo group and the other is a methoxy or ethoxy group, Y is a fluorine or chlorine atom or an arylamino group substituted with one or two sulfo groups, R is a hydrogen atom or an unsubstituted or substituted lower alkyl group, A is an unsubstituted or substitued phenylene or naphthylene group, and Z is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub..sub.2 CH.sub.2 Z.sub.1 in which Z.sub.1 is a group capable of being split by the action of an alkali, which is useful as a fiber-reactive dye for dyeing materials in a greenish yellow color excellent in various fastness properties.
    Type: Grant
    Filed: November 13, 1985
    Date of Patent: June 27, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yutaka Kayane, Hirokazu Sawamoto, Takashi Omura, Naoki Harada, Akira Takeshita
  • Patent number: 4843148
    Abstract: A process for the preparation of reactive dyes of the formula ##STR1## in which D, R and Z are as defined in greater detail in the description, which comprises subjecting 2,4,6-trifluoro-s-triazine to a condensation reaction in a strongly acid solution and in the presence of an alkali metal fluoride with an amine of the formulaH--Z (3)and then subjecting the primary condensation product obtained to a condensation reaction with an amino dye of the formula ##STR2## affords reactive dyes of the formula (1) in a high yield and a high state of purity.
    Type: Grant
    Filed: December 23, 1986
    Date of Patent: June 27, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Emil Bonometti, Herbert Seiler
  • Patent number: 4841030
    Abstract: They are useful for dyeing and printing materials containing hydroxyl groups or amide groups.
    Type: Grant
    Filed: December 4, 1981
    Date of Patent: June 20, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventor: Horst Jager
  • Patent number: 4841027
    Abstract: Improvement in a process for producing an arylazo-aminonaphtholsulfonic acid represented by a free acid of the formula, ##STR1## wherein A is a phenyl or naphthyl group unsubstituted or substituted by one to four members selected from alkyl, alkoxy, phenoxy, sulfonic acid, carboxylic acid, arylamino, amino, nitro and hydroxyl groups and halogen atoms, and m is 0 or 1, which comprises reacting an aminonaphtholsulfonic acid represented by a free acid of the formula, ##STR2## wherein m is as defined above, with a dibasic acid anhydride to obtain an acylaminonaphtholsulfonic acid, coupling a diazonium compound of amine of the formula,A'--NH.sub.
    Type: Grant
    Filed: February 11, 1985
    Date of Patent: June 20, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yutaka Kayane, Takashi Omura, Yasuo Tezuka, Hideharu Sone
  • Patent number: 4840642
    Abstract: Compounds of the formula ##STR1## and salts thereof, useful for dyeing and printing hydroxy group - or nitrogen-containing organic substrates, for example, leather and fibrous materials containing or consisting of natural or synthetic polyamides or natural or regenerated cellulose; preferably textile material containing or consisting of cotton which is preferably dyed using the exhaust dyeing method.
    Type: Grant
    Filed: September 4, 1987
    Date of Patent: June 20, 1989
    Assignee: Sandoz Ltd.
    Inventors: Gunther Auerbach, Helmut A. Moser
  • Patent number: 4841029
    Abstract: 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: Grant
    Filed: April 19, 1988
    Date of Patent: June 20, 1989
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Yoshiaki Kato, Toshio Hihara
  • Patent number: 4841031
    Abstract: 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: Grant
    Filed: September 7, 1984
    Date of Patent: June 20, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yutaka Kayane, Katsumasa Otake, Yasuo Tezuka
  • Patent number: 4841028
    Abstract: Reactive dyes of the formula ##STR1## in which D 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, R is hydrogen or substituted or unsubstituted C.sub.1-4 -alkyl, A is a polymethylene radical having 2 to 6 C atoms (or its branched isomers) which can be substituted by chlorine, bromine, fluorine, hydroxyl, sulfato, acyloxy having 1 to 4 C atoms, cyano, carboxyl, alkoxycarbonyl having 1 to 5 C atoms or carbamoyl, or an alkyleneoxalkylene radical having 1 to 6 C atoms in each alkylene member, independently of each other; Y is a radical --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.
    Type: Grant
    Filed: August 10, 1987
    Date of Patent: June 20, 1989
    Inventors: Peter Aeschlimann, Hansrudolf Schwander
  • Patent number: 4841033
    Abstract: 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: Grant
    Filed: September 29, 1987
    Date of Patent: June 20, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshihiko Morimitsu, Sadanobu Kikkawa, Naoki Harada, Takashi Omura
  • Patent number: 4839468
    Abstract: 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: Grant
    Filed: November 13, 1984
    Date of Patent: June 13, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Nickel, Peter Wild, Frank-Michael Stohr
  • Patent number: 4837310
    Abstract: 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: Grant
    Filed: January 9, 1987
    Date of Patent: June 6, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshihiko Morimitsu, Sadanobu Kikkawa, Takashi Omura
  • Patent number: 4833235
    Abstract: Disazo compounds of the formula ##STR1## and salt thereof, D is the radical of a diazo component of the benzene or naphthalene series.K is the radical of a heterocyclic coupling component of the aminopyrazole-, pyridone- or barbituric acid-series, n is 1 to 4,R.sub.1 is hydrogen, C.sub.1-4 alkyl or substituted C.sub.1-4 alkyl,each of R.sub.2 and R.sub.3 is independently hydrogen, halo, C.sub.1-4 alkyl, substituted C.sub.1-4 alkyl, C.sub.1-4 alkoxy, substituted C.sub.1-4 alkoxy, --NHCO--Rhd 5, amino, substituted amino or a quaternary ammonium group, wherein R.sub.5 is C.sub.1-4 alkyl, substituted C.sub.1-4 alkyl, C.sub.1-4 alkoxy or amino,R.sub.4 is hydrogen, C.sub.1-4 alkyl, C.sub.
    Type: Grant
    Filed: October 7, 1987
    Date of Patent: May 23, 1989
    Assignee: Sandoz Ltd.
    Inventor: Reinhard Pedrazzi
  • Patent number: 4818247
    Abstract: Reactive dyes of the formula ##STR1## in which D is the radical of a diazo component of the benzene, naphthalene, azobenzene, naphthylazobenzene, azonaphthalene or phenylazonaphthalene series, K is the radical of a coupling component of the benzene or naphthalene series or of the heterocyclic series, except a pyrazolone radical, R.sub.1 and R.sub.2, independently of each other, are each hydrogen or an unsubstituted or substituted C.sub.1-4 -alkyl radical, and X.sub.1 and X.sub.2, independently of each other, are each unsubstituted or substituted aminofluoro-s-triazinyl, are particularly suitable for dyeing and printing cellulose-containing fibre materials and produce, in high dyeing yield, dyeings and prints having good fastness properties.
    Type: Grant
    Filed: May 21, 1987
    Date of Patent: April 4, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Adolf Kaser
  • Patent number: 4812558
    Abstract: 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: Grant
    Filed: November 10, 1987
    Date of Patent: March 14, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takashi Omura, Kazufumi Yokogawa
  • Patent number: 4808706
    Abstract: Dyes of the formula ##STR1## wherein D is the radical of an organic dye, R.sub.1 is hydrogen or methyl, R.sub.2 is alkyl of 2 to 4 carbon atoms, and X is hydrogen or methyl.
    Type: Grant
    Filed: February 14, 1984
    Date of Patent: February 28, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Herbert Seiler
  • Patent number: 4801694
    Abstract: Reactive dyes of the formula ##STR1## in which D is the radical of an organic dye of the monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthrone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide series, R is hydrogen or substituted or unsubstituted C.sub.1-4 -alkyl, X is a substituent which is detachable as an anion, B is a radical of the formula ##STR2## R.sub.1 and R.sub.2, independently of each other, are hydrogen or substituted or unsubstituted C.sub.1-4 -alkyl or phenyl, A is a substituted or unsubstituted aliphatic or aromatic bridge member, Y is a --CO--Z or --SO.sub.2 --Z radical, Z is an aliphatic, aromatic or heterocyclic reactive radical, and n is 1 or 2, are suitable for dyeing or printing cellulose-containing and nitrogen-containing materials and in high dyeing yield produce dyeings and prints having good fastness properties.
    Type: Grant
    Filed: July 13, 1987
    Date of Patent: January 31, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Scheibli, Karl Seitz, Herbert Seiler, Athanassios Tzikas
  • Patent number: 4786721
    Abstract: 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: Grant
    Filed: August 13, 1986
    Date of Patent: November 22, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Peter Aeschlimann, Paul Herzig
  • Patent number: 4785081
    Abstract: A new process for the production of reactive dyes by the reaction of cyanuric chloride with anionic dyes containing an amino group, which process comprises the adiabatic reaction of cyanuric chloride with the dye, at a temperature of 20.degree. to 80.degree. C. and a pH value of between 3.0 to 7.0, with the rapid addition of the educts within 1 to 30 minutes, produces reactive dyes in good yield and purity and is technically advantageous.
    Type: Grant
    Filed: September 22, 1986
    Date of Patent: November 15, 1988
    Assignee: Ciba-Geigy AG
    Inventor: Karlheinz Franke
  • Patent number: 4782140
    Abstract: 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: Grant
    Filed: October 2, 1986
    Date of Patent: November 1, 1988
    Assignee: Ciba-Giegy Corporation
    Inventor: Athanassios Tzikas
  • Patent number: 4780532
    Abstract: A water-soluble dye, free from cellulose reactive groups, of the formula: ##STR1## wherein R.sup.1 is --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H,R.sup.2 is H or --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H, orR.sup.1 & R.sup.2 together with the nitrogen atom form a morpholine ringa & b are different and from 1 to 8m is from 1 to 10;n is from 0 to 9;q is 1/2 or 1p is 1 or 2L is a transition metal capable of complexing with a dyeM is H, ammonium, or a monovalent metal;B, D, F & E are H or substituents;X is NR.sup.1 R.sup.2, NR.sup.3 R.sup.4, --NR.sup.3 --Z--NR.sup.4 --, OR.sup.3, or the residue of a mono- or dis-azo chromophore comprising benzene, naphthalene or hetero-mono- or bi-cyclic diazo and coupling components, linked to the triazine nucleus through a primary or secondary amino linking group in which R.sup.3 and R.sup.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: October 25, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
  • Patent number: 4777247
    Abstract: 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: Grant
    Filed: April 6, 1987
    Date of Patent: October 11, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hermann Henk
  • Patent number: 4775746
    Abstract: 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: Grant
    Filed: September 30, 1986
    Date of Patent: October 4, 1988
    Assignee: Hoechst Aktiengesellshaft
    Inventors: Hartmut Springer, Michael Kunze, Marcos Segal, Werner H. Russ
  • Patent number: 4766206
    Abstract: 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: Grant
    Filed: September 24, 1986
    Date of Patent: August 23, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanassios Tzikas
  • Patent number: 4764175
    Abstract: Metal-free compounds of the formula, ##STR1## and 1:1 copper complexes of metallizable metal-free compounds of said formula and internal and external salts of metal-free compounds of said formula and of 1:1 copper complexes of metallizable metal-free compounds of said formula, whereineach Q is independently linear or branched C.sub.2-6 alkylene; linear or branched C.sub.2-6 alkylene interrupted by --O--, --S-- or --NR.sub.4 --; linear or branched C.sub.3-6 alkylene monosubstituted or disubstituted by hydroxy or --*NHCO--CH.sub.2 --, wherein the * denotes the atom attached to the --NR.sub.4 -- radical,each R.sub.1 is independently hydrogen, halo, nitro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, (C.sub.1-4 alkyl)carbonylamino, --SO.sub.2 NR.sub.3 R.sub.4, --CONR.sub.4 --C.sub.6 H.sub.5 or benzamido,R.sub.2 is hydrogen, hydroxy, halo, nitro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, (C.sub.1-4 alkyl)carbonylamino or --NHCONR.sub.3 R.sub.4,X is --NR.sub.5 R.sub.6 or --N.sup..sym. R.sub.7 R.sub.8 R.sub.9 An.sup..crclbar.
    Type: Grant
    Filed: August 15, 1986
    Date of Patent: August 16, 1988
    Assignee: Sandoz Ltd.
    Inventors: Jacky Dore, Reinhard Pedrazzi
  • Patent number: 4762916
    Abstract: 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: Grant
    Filed: December 23, 1986
    Date of Patent: August 9, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ludwig Schlafer, Hartmut Springer, Michael Kunze
  • Patent number: 4757136
    Abstract: 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: Grant
    Filed: September 30, 1986
    Date of Patent: July 12, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Springer, Michael Kunze, Marcos Segal, Werner H. Russ