Chalcogen Or Carbon Bonded Directly To The Six-membered Hetero Ring And Is Between The Hetero Ring And The Azo Group Patents (Class 534/626)
  • Patent number: 6271355
    Abstract: Dyes of Formula (1) which are useful for the coloration of e.g. cellulosic materials and leathers. wherein: NiPc is a nickel phthalocyanine radical; r has a value from 1 to 3 inclusive; m has a value from 1 to 3 inclusive; p has a value from 0 to 1 inclusive; R1 is H, alkyl, substituted alkyl, aryl or substituted aryl; R2, R3 and R4 are each independently H, C1-6-alkyl or substituted C1-6-alkyl; A is phenylene, substituted phenylene, C1-6-alkylene or substituted C1-6-alkylene; Q is a labile substituent; B is phenylene, phenylene substituted by 1 or 2 sulpho groups or phenylene substituted by an alkyl or alkoxy group; Z is H or alkyl; and X and Y are each independently H, alkyl, alkoxy, halogen, carboxy or sulpho; provided that r+m+p does not exceed 4.
    Type: Grant
    Filed: August 17, 1993
    Date of Patent: August 7, 2001
    Assignee: Imperial Chemical Industries PLC
    Inventors: Denis Robert Annesley Ridyard, Andrew Hunter Morris Renfrew
  • Patent number: 5319074
    Abstract: A metal-free dyestuff of the formula ##STR1## and metal complex thereof wherein: Fb=the radical of a dyestuff selected from the group consisting of mono- or polyazo, anthraquinone, phthalocyanine, formazan, dioxazine and triphenylmethane radicals,B and B'=a direct bond or an aliphatic or aromatic bridge member to a ring C atom of an aromatic-carbocyclic ring or to a ring C or N atom or an aromatic-heterocyclic ring in Fb,X=CH.dbd.CH.sub.2 or CH.sub.2 CH.sub.2 --Y, whereinY=OSO.sub.3 H, SSO.sub.3 H, OCOCH.sub.3, OPO.sub.3 H.sub.2, OSO.sub.2 CH.sub.3, SCN, NHSO.sub.2 CH.sub.3 --, Cl, Br, F, OCOC.sub.6 H.sub.5, OSO.sub.2 --C.sub.6 H.sub.4 CH.sub.3, ##STR2## R=H or C.sub.1 -C.sub.4 -alkyl, which is optionally be substituted by halogen, hydroxy, cyano, C.sub.1 -C.sub.4 -alkoxy, carboxyl, sulpho or sulphato,Z=a fiber-reactive radical of the formula ##STR3## wherein M=H, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -thioalkyl, F or CF.sub.
    Type: Grant
    Filed: January 24, 1992
    Date of Patent: June 7, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfram Reddig, Karl-Josef Herd, Ernst Kysela
  • Patent number: 5298607
    Abstract: 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: Grant
    Filed: May 26, 1993
    Date of Patent: March 29, 1994
    Assignee: Ciba-Geigy Corporation
    Inventor: Herbert Seiler
  • Patent number: 5003052
    Abstract: 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: Grant
    Filed: May 11, 1988
    Date of Patent: March 26, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanassios Tzikas
  • Patent number: 4963660
    Abstract: Free radical heavy metal ions in water-soluble heavy metal complex dyestuffs are removed from the synthesis solution of the heavy metal complex dyestuff by means of a compound or several of the compounds mentioned below:(a) saturated and unsaturated fatty acids having about 8 to 18 carbon atoms and water-soluble salts thereof;(b) the monoesters and diesters of orthophosphoric acid and salts thereof corresponding to the general formula (1a) and (1b) ##STR1## in which R denotes a saturated or unsaturated aliphatic radical having about 8 to 18 carbon atoms and M stands for a hydrogen atom or a salt-forming, water-solubilizing metal;(c) aliphatic sulfonic acids and water-soluble salts thereof corresponding to the general formula (2)R--SO.sub.
    Type: Grant
    Filed: August 30, 1988
    Date of Patent: October 16, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Uwe Mrotzeck, Peter Mischke, Gunther Schwaiger, Werner Russ, Manfred Sittig
  • 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: 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: 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: 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: 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: 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: 4723001
    Abstract: The invention relates to chromium complexes of the formula ##STR1## in which B is the radical of a bidentate bianionic compound, L is H.sub.2 O, NH.sub.3, alkanol, alkylamine, dialkylamine, trialkylamine or pyridine, D is a benzene or naphthalene diazo component, Y is the nitrogen atom or the CH group, K is a coupling component, R is hydrogen, alkyl or phenyl, X is a fibre-reactive group,Ka is a cation, m is 1, 2 or 3, n is 1 or 2 and k is 0 or 1.These chromium complexes are suitable for dyeing nitrogen-containing or hydroxy-containing materials and they produce level dyeings having good all-round fastness properties.
    Type: Grant
    Filed: July 24, 1986
    Date of Patent: February 2, 1988
    Assignee: CIBA-GEIGY Corporation
    Inventors: Hans U. Schutz, Ulrich Schlesinger, Gerhard Back
  • Patent number: 4707545
    Abstract: 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: Grant
    Filed: November 26, 1985
    Date of Patent: November 17, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Fritz Meininger, Ludwig Schlafer
  • Patent number: 4677199
    Abstract: Compounds of the general formula I ##STR1## wherein R.sup.1 is hydrogen, fluorine, chlorine or bromine, R.sup.2 is hydrogen, fluorine, chlorine, bromine, or nitro, B is aliphatic or a sulfo-substituted phenylene radical, and X is a dye radical, are useful for dyeing hydroxyl-containing textile material, in particular cotton.
    Type: Grant
    Filed: September 19, 1985
    Date of Patent: June 30, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Dietmar Augart, Heinz Eilingsfeld, Heinz Krueger, Hartmut Lardon, Ortwin Schaffer, Guenther Seybold