The Hetero Ring Is Six-membered And Contains At Least Two Nitrogens Patents (Class 534/622)
  • Patent number: 7887602
    Abstract: Reactive dyes of formula wherein the variables are defined herein.
    Type: Grant
    Filed: August 2, 2006
    Date of Patent: February 15, 2011
    Assignee: Huntsman International, LLC
    Inventors: Hubert Jean Luc Christnacher, Athanassios Tzikas, Georg Roentgen
  • Patent number: 7439340
    Abstract: A reactive dyestuff containing an alkylthio-s-triazinyl reactive group of the following formula (I) is disclosed, wherein A, X, Y, Z, R, Q, and a are defined the same as the specification. It is suitable for exhaust dyeing, cold batch-up dyeing and continuous dyeing materials that contain hydroxyl group or nitrogen group fibers.
    Type: Grant
    Filed: February 15, 2007
    Date of Patent: October 21, 2008
    Assignee: Everlight USA, Inc.
    Inventors: Wen-Jang Chen, Hsien-Chung Shia, Duncan Adrian Sidney Phillips, John Anthony Taylor
  • Publication number: 20080207881
    Abstract: A reactive dyestuff containing an alkylthio-s-triazinyl reactive group of the following formula (I) is disclosed, wherein A, X, Y, Z, R, Q, and a are defined the same as the specification. It is suitable for exhaust dyeing, cold batch-up dyeing and continuous dyeing materials that contain hydroxyl group or nitrogen group fibers.
    Type: Application
    Filed: April 30, 2008
    Publication date: August 28, 2008
    Applicant: Everlight USA, Inc.
    Inventors: Wen-Jang Chen, Hsien-Chung Shia, Duncan Adrian Sidney Phillips, John Anthony Taylor
  • Patent number: 7105645
    Abstract: Dyes of general formula (I) wherein R1, R2, M, Y and x have the meaning cited in the description, the production and use thereof for dyeing or printing material containing hydroxy and/or carbonamide groups, preferably fiber material.
    Type: Grant
    Filed: April 22, 2003
    Date of Patent: September 12, 2006
    Assignee: DyStar Textilfarben GmbH & Co. Deutschland KG
    Inventors: Günther Schwaiger, Stefan Meier, Werner Russ
  • Patent number: 7087730
    Abstract: Reactive dyes of formula (I), wherein A is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan or dioxazine chromophore, Q1, and Q2 are each independently of the other hydrogen or unsubstituted or substituted C1–C4alkyl, (Q3)n denotes n substituents selected from the group C1–C4alkyl, C1–C4alkoxy, halogen and sulfo, X is halogen, 3-carboxypyridin-1-yl, 3-carbamoylpyridin-1-yl, hydroxy, C1–C4alkoxy unsubstituted or substituted in the alkyl moiety, phenoxy unsubstituted or substituted in the phenyl moiety, C1–C4alkylthio unsubstituted or substituted in the alkyl moiety, unsubstituted or substituted amino, or an N-heterocycle which may or may not contain further hetero atoms, Y is vinyl or a radical —CH2—CH2—U and U is a group removable under alkaline conditions, k is a number 2, 3, 4, 5 or 6, m is a number 0 or 1, and n is a number 0, 1 or 2, with the proviso that when A denotes a monoazo chromophore it is not directly linked to the triazinyl radical through a hydroxyna
    Type: Grant
    Filed: July 15, 2003
    Date of Patent: August 8, 2006
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Athanassios Tzikas, Bernhard Müller, Georg Roentgen
  • Patent number: 6974497
    Abstract: Claimed are compounds of formula (I) where the substituents are each as defined in the claims, their preparation, their use as dyes and as a ingredients of an ink-jet printing ink and also substrates dyed with such compounds.
    Type: Grant
    Filed: September 27, 2001
    Date of Patent: December 13, 2005
    Assignee: Clariant Finance (BVI) Limited
    Inventor: Rainer Nusser
  • Patent number: 6852135
    Abstract: Dyes of the general formula (1): where M is hydrogen, alkali, ammonium or the equivalent of an alkaline earth metal ion, X is halogen, alkoxy or an N-containing heterocycle, Q is a grouping of the formula (e) where Y is vinyl or an alkali-eliminable grouping and W is alkyl which may be interrupted by an O or an NR group and the radicals R1 and R2 represent alkyl, alkoxy, alkylcarbonylamino, arylcarbonylamino, and also the radicals R3 and R4 are alkyl or hydrogen, their preparation and their use for dyeing and printing hydroxyl- and/or carboxamido-containing material, preferably fiber material.
    Type: Grant
    Filed: July 14, 2001
    Date of Patent: February 8, 2005
    Assignee: DyStar Textilfarben GmbH & Co. Deutschland KG
    Inventors: Joachim Steckelberg, Hermann Henk
  • Patent number: 6809187
    Abstract: Reactive copper, cobalt or chromium complex compounds of the general formula (1) where R1-R5, M, Me, W1, X, k, l and m are each as defined in claim 1, processes for their preparation and their use for dyeing or printing textile fiber materials.
    Type: Grant
    Filed: April 10, 2003
    Date of Patent: October 26, 2004
    Assignee: Oystar Textil Farben GmbH & Co.
    Inventors: Stefan Ehrenberg, Klaus Kunde
  • Patent number: 6329514
    Abstract: A fiber reactive dyestuff of the following formula (I) wherein the definition of D, and Z the same meaning as given in the description. The fiber reactive dyestuff of the present invention is suitable for dyeing and printing on cellulose fiber or fiber materials containing cellulose. Dyed material with various excellent properties in dyed color can be obtained, showing especially outstanding performance in the property of wash fastness.
    Type: Grant
    Filed: February 8, 2000
    Date of Patent: December 11, 2001
    Assignee: Everlight USA, Inc.
    Inventors: Huei Ching Huang, Keh Loong Chen, Mao Cheng Hsu, Ta Chung Yin
  • Patent number: 5721343
    Abstract: Fiber-reactive monoazo and disazo compounds of the formulaD-N.dbd.N--Kwhich compounds are in free acid or salt form, and mixtures thereof, are useful for dyeing or printing hydroxy group- or nitrogen-containing organic substrates, for example leather and fiber material comprising natural or synthetic polyamides or natural or regenerated cellulose; the most preferred substrate is a textile material comprising cotton.
    Type: Grant
    Filed: May 2, 1995
    Date of Patent: February 24, 1998
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Paul Doswald, Rainer Nusser, Roland Wald
  • Patent number: 5717077
    Abstract: A phthalocyanine monoazo compound which is represented by the following formula (I): ##STR1## wherein Pc represents a phthalocyanine group; M represents nickel, cobalt or copper;R.sub.1 represents a hydrogen atom or a lower alkyl group;R.sub.2 and R.sub.3 represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a sulfo group;R.sub.4 represents a hydrogen or a lower alkyl group;A represents a group containing a triazine group or a pyrazole group and/or --SO.sub.2 X wherein X represents --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 Y and Y represents a group splittable by the action of an alkali;p is a number of 0-2; q is a number of 1-3; r is a number of 1-2; p+q+r is 4 or lessor which is a salt of the compound of formula (I).
    Type: Grant
    Filed: December 11, 1995
    Date of Patent: February 10, 1998
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshiyuki Araki, Takemi Tokieda, Shin-ichi Yabushita, Yasuyoshi Ueda, Bunzi Tsukise
  • Patent number: 5597902
    Abstract: Reactive dyestuffs which, in the form of the free acid, correspond to the following formula ##STR1## wherein D is the radical of an organic dyestuff of the monoazo, polyazo or metal complex azo series and the other substituents have the meaning given in the description, show improved application properties.
    Type: Grant
    Filed: April 27, 1993
    Date of Patent: January 28, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Konrad Bootz, Manfred Hoppe, Eckhard Bock, Wolfram Reddig, Thomas Eizenh ofer, Wolfgang Harms, Karl-Joseph Herd
  • Patent number: 5583207
    Abstract: Fibre-reactive 1:1 copper complexes of the formula ##STR1## which compounds are in free acid or salt form, and mixtures thereof, are useful for dyeing or printing hydroxy group- or nitrogen-containing organic substrates, for example leather and fibre material comprising natural or synthetic polyamides or natural or regenerated cellulose; the most preferred substrate is a textile material comprising cotton.
    Type: Grant
    Filed: May 2, 1995
    Date of Patent: December 10, 1996
    Assignee: Sandoz Ltd.
    Inventors: Rainer Nusser, Roland Wald
  • Patent number: 5548071
    Abstract: The invention relates to compounds of the formula ##STR1## where the variables are each as defined in the claims. The compounds are suitable for use as dyes, in particular for dyeing and printing cellulose-containing fibre materials and produce dyeings and prints having good allround fastness properties.
    Type: Grant
    Filed: May 13, 1994
    Date of Patent: August 20, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Rolf Deitz, Athanassios Tzikas, Paul Herzig
  • Patent number: 5484899
    Abstract: The invention relates to compounds of the formula ##STR1## in which the variables are as defined in the claims. The compounds are suitable as dyes, in particular for dyeing and printing cellulosic fibre materials, and produce dyeings and prints with good all-round fastness properties.
    Type: Grant
    Filed: May 3, 1994
    Date of Patent: January 16, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Rolf Deitz, Athanassios Tzikas
  • Patent number: 5455334
    Abstract: Phthalocyanine compounds which contain a heterocyclic fibre-reactive radical correspond to the formula ##STR1## in which the symbols are as defined in the specification, which compounds are in free acid or salt form, and mixtures thereof, are useful for dyeing or printing hydroxy group- or nitrogen-containing organic substrates, for example leather and fibre material comprising natural or synthetic polyamides or natural or regenerated cellulose; the most preferred substrate is a textile material comprising cotton.
    Type: Grant
    Filed: February 10, 1994
    Date of Patent: October 3, 1995
    Inventor: Roland Wald
  • Patent number: 5359043
    Abstract: A water soluble dye having a reactive group of the formula: ##STR1## wherein: T is a labile atom or group; andR.sup.2 and R.sup.3 are each independently a non-chromophoric optionally substituted aryl or alkyl group.
    Type: Grant
    Filed: April 21, 1992
    Date of Patent: October 25, 1994
    Assignee: Zeneca Limited
    Inventors: Stephen B. Bostock, Michael G. Hutchings, John A. Taylor
  • Patent number: 5349057
    Abstract: Water-soluble azo dyes and their heavy metal complex derivatives, such as copper, cobalt and chromium complex azo dyes are described, which have the general formula (1) shown below, have fiber-reactive properties and dye natural and synthetic hydroxyl- and/or carboxamido-containing materials, in particular fiber materials, such as wool and in particular cellulose fiber materials, by the dyeing and printing processes customary for fiber-reactive dyes, in hues which have high color strength and good fastness properties.
    Type: Grant
    Filed: January 10, 1992
    Date of Patent: September 20, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Holger M. Buch, Hartmut Springer
  • 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: 5278292
    Abstract: Water-soluble fiber-reactive dyes are described conforming to the below-indicated formula (1) which are capable of dyeing hydroxyl- and/or carboxamido-containing material, in particular fiber material, such as wool and in particular cellulose fiber materials, in strong, fast shades. ##STR1## in which F is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, triphenoldioxazine, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, formazan, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye;R.sup.x is hydrogen or alkyl of 1 to 4 carbon atoms;R is hydrogen, sulfo, carboxyl, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or chlorine;w is 1, 2, 3 or 4;Y is vinyl or an ethyl group which contains in the .beta.-position a substituent which is eliminable by alkali to form a vinyl group;n is 1 or 2.
    Type: Grant
    Filed: July 17, 1992
    Date of Patent: January 11, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Springer, Rolf Gleissner, Gunther Schwaiger
  • Patent number: 5268457
    Abstract: Reactive dyes of the formula ##STR1## are particularly suitable for dyeing or printing cellulosic fibre materials by the exhaust method or by continuous processes and give, with a high color yield, dyeings and prints with good fastness properties, in which D is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye; R is hydrogen or alkyl having 1 to 4 carbon atoms, which can be substituted by hydroxyl, cyano, carboxyl, sulfo or sulfato; X is fluorine or chlorine; B is a substituted or unsubstituted aliphatic or aromatic bridge member; Y is a substituted or unsubstituted aliphatic, aromatic, araliphatic or heterocyclic radical, which is free from reactive groups; R.sub.2 is hydrogen or alkyl having 1 to 4 carbon atoms, which can be substituted by halogen, hydroxyl, cyano, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.
    Type: Grant
    Filed: December 28, 1992
    Date of Patent: December 7, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanassios Tzikas
  • Patent number: 5256773
    Abstract: The reactive dyes of the formula ##STR1## in which the substituents and indices have the meaning given in the description, are outstandingly suitable for dyeing or printing naturally occurring or synthetic materials containing hydroxyl or amide groups.
    Type: Grant
    Filed: December 14, 1992
    Date of Patent: October 26, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Kunde, Hermann Henk, Karl-Heinz Schundehutte, deceased, Frank-Michael Stohr
  • Patent number: 5231171
    Abstract: Reactive dyes useful for dyeing or printing hydroxyl- or nitrogen-containing substrates have the formula ##STR1## where Rg is a radical of the formula ##STR2## Ar is the radical of a benzene or naphthalene ring, Z.sup.1 and Z.sup.2 are each hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, substituted or unsubstituted phenyl, C.sub.1 -C.sub.4 -alkoxy, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, cyano, halogen or hydroxysulfonyl,Z.sup.3, Z.sup.4 and Z.sup.5 are each hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or substituted or unsubstituted phenyl,U is a group which is detachable under alkaline reaction conditions,X is in case a) the radical of a chromophore or in case b) the radical of a coupling component to which may additionally be attached, via an azo bridge, the radical of a diazo component and which may have additional reactive groups, andL is in case a) a bridge member or in case b) an azo bridge.
    Type: Grant
    Filed: December 13, 1991
    Date of Patent: July 27, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Claus Marschner, Matthias Niedenbrueck, Bernd Siegel, Manfred Patsch, Klaus Pandl
  • Patent number: 5210187
    Abstract: Double attachment reactive dyes have the formula ##STR1## where U.sup.1 is C.sub.1 -C.sub.4 -alkyl, phenyl, C.sub.2 -C.sub.10 -alkenyl or the radical ##STR2## where Q.sup.1 and Q.sup.2 are each independently of the other hydrogen or C.sub.1 -C.sub.4 -alkyl and Q.sup.3 is a group which is detachable under alkaline reaction conditions,Z is the radical ##STR3## where each Q.sup.4 is independently of the other hydrogen or C.sub.1 -C.sub.4 -alkyl which may be substituted by cyano, U.sup.2 is C.sub.1 -C.sub.4 -alkyl, phenyl, C.sub.2 -C.sub.10 -alkenyl or the radical ##STR4## where Q.sup.5 and Q.sup.6 are each independently of the other hydrogen or C.sub.1 -C.sub.4 -alkyl and Q.sup.7 is a group which is detachable under alkaline reaction conditions, and w is 0, 1 or 2,t is 0, 1 or 2,v is 1 or 2 and X and L are each as defined in the description, with the proviso that at least one of the two radicals U.sup.1 and U.sup.2 is not C.sub.1 -C.sub.
    Type: Grant
    Filed: April 9, 1992
    Date of Patent: May 11, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Manfred Patsch, Uwe Nahr, Friedrich Wirsing, Joerg L. Jessen, Klaus Pandl, Claus Marschner, Matthias Dust
  • Patent number: 5106958
    Abstract: Compounds of the formula ##STR1## and salts thereof, wherein R.sub.1 is hydrogen, chloro, bromo, carboxy or sulfo,R.sub.2 is hydrogen or C.sub.1-4 alkyl,R.sub.3 is hydrogen, C.sub.1-4 alkyl or C.sub.1-4 hydroxyalkyl, andR.sub.4 is C.sub.1-6 alkyl monosubstituted by carboxy or sulfo; C.sub.2-6 alkyl monosubstituted by hydroxy or --OR.sub.5 ; C.sub.2-6 dihydroxyalkyl the hydroxy groups of which are on different carbon atoms; phenyl or phenyl monosubstituted or disubstituted by C.sub.1-4 alkyl,wherein R.sub.5 is C.sub.2-4 hydroxyalkyl, with the proviso that when each of R.sub.1, R.sub.2 and R.sub.3 is hydrogen, R.sub.4 is other than 2-hydroxyethyl, and mixtures of such complexes and salts, useful for dyeing or printing hydroxy group- or nitrogen-containing organic substrates, for example leather and fiber materials containing or consisting of natural or synthetic polyamides or of natural or regenerated cellulose, preferably textile material containing or consisting of cotton.
    Type: Grant
    Filed: March 22, 1991
    Date of Patent: April 21, 1992
    Assignee: Sandoz Ltd.
    Inventor: Werner Koch
  • Patent number: 5021558
    Abstract: Water-soluble fiber-reactive azo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylemthane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dyes which contain once or twice the group of the general formula ##STR1## in which: R.sup.x and R.sup.z are, independently of one another, hydrogen or lower alkyl, which can be substituted by halogen, hydroxyl, cyano, lower alkoxy, lower alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato;W is fluorine, chlorine, bromine, sulfo, phenylsulfonyl or alkylsulfonyl of 1 to 4 carbon atoms;Y is vinyl, .beta.-substituted, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-alkanoyloxyethyl of 2 to 5 carbon atoms in the alkanoyl radical, .beta.-benozoyloxyethyl, .beta.-(sulfobenzoyloxy)ethyl, .beta.-(p-toluenesulfonyloxy)ethyl or .beta.-halogenoethyl.
    Type: Grant
    Filed: March 20, 1990
    Date of Patent: June 4, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Holger M. Buch
  • Patent number: 5015732
    Abstract: Water-soluble copper complex monoazo compounds of the general formula (1) ##STR1## in which D denotes the radical of a diazo component of the benzene or naphthalene series with the oxy group in the ortho-position relative to the azo bridge, K denotes the radical of a coupling component of the benzene, naphthalene, pyridone or pyrazolone series with the phenolic or enolic oxy group in ortho-position relative to the azo group, R denotes hydrogen or alkyl of 1 to 4 C atoms, Y denotes the radical of the formula --NH--, --N(lower alkyl)-- or --CH.sub.2 --, n represents the number zero or 1, Z denotes the vinyl, .beta.-acetoxyethyl, .beta.-thiosulfatoethyl, .beta.-chloroethyl or .beta.-sulfatoethyl group and X denotes a radical of the general formula (2a), (2b) or (2c) ##STR2## in which R.sup.1 is an optionally substituted alkyl radical, an optionally substituted aryl radical or an optionally substituted heteroaromatic radical, R.sup.
    Type: Grant
    Filed: March 29, 1988
    Date of Patent: May 14, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Fritz Meininger
  • 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: 5001227
    Abstract: The invention relates to chromium complexes of the formula ##STR1## in which L is H.sub.2 O, NH.sub.3, R.sub.2 --OH, R.sub.2 --NH.sub.2, (R.sub.2).sub.2 NH, (R.sub.2).sub.3 N or pyridine, wherein R.sub.2 is C.sub.1-6 -alkyl unsubstituted or substituted by halogen, C.sub.1-4 -alkoxy or amino, B is 8-hydroxyquinoline, 5-chloro-8-hydroxyquinoline, 5-hydroxyacridine, 6-hydroxy-4,7-phenanthroline, pyridine-2-carboxylic acid, 8-carboxyquinoline, 5,7-dibromo-8-hydroxyquinoline, o-hydroxyaniline, o-hydroxynaphthylamine, proline, glycine, serine, aspartic acid or R.sub.1 --CH(NH.sub.2)--COOH, wherein R.sub.1 is C.sub.1-6 -alkyl unsubstituted or substituted by halogen, C.sub.
    Type: Grant
    Filed: November 9, 1984
    Date of Patent: March 19, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans U. Schutz, Ulrich Schlesinger, Gerhard Back
  • Patent number: 4997918
    Abstract: Novel cationic azo compounds of the formula ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.4 -alkylene, R.sub.2 is C.sub.1 -C.sub.4 -alkyl, R.sub.3 is C.sub.1 -C.sub.4 -alkyl, R.sub.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, acylamino or halogen, R.sub.5 is hydrogen, C.sub.1 -C.sub.4 - alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen, one or more or R.sub.5 independently of each other being present on the ring to which R.sub.5 is attached, and A is an anion. Also provided is the production, and the use of these novel compounds as dyes for dyeing and/or printing, especially polyacrylonitrile materials, neutral blue dyeings having in particular good fastness to light being obtained.
    Type: Grant
    Filed: May 6, 1987
    Date of Patent: March 5, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Zink
  • Patent number: 4996304
    Abstract: 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: Grant
    Filed: February 23, 1990
    Date of Patent: February 26, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanassios Tzikas
  • Patent number: 4990598
    Abstract: The invention relates to chromium complexes of the formula ##STR1## in which A is the radical of a dicyclically metallizable azo or azomethine dye, B is the radical of a monoanionic bidentate complexible organic compound which is bonded to the chromium atom via oxygen atoms, L is a colorless monofunctional ligand, X is halogen-substituted C.sub.1-4 -alkanoyl, C.sub.1-4 -alkenoyl, halogen-substituted C.sub.1-4 -alkenoyl, monohalogenopyrimidinyl, dihalogenopyrimidinyl or trihalogenopyrimidinyl which is bonded to A and/or B via ##STR2## and R.sub.5 is hydrogen or C.sub.1-4 -alkyl, Ka is a cation, m is 1, 2 or 3, n is 1 or 2 and the SO.sub.3.sup..crclbar. Ka group is bonded to A and/or B. 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: November 7, 1984
    Date of Patent: February 5, 1991
    Inventors: Hans U. Schutz, Ulrich Schlesinger, Gerhard Back
  • Patent number: 4968781
    Abstract: A reactive dye of the formula ##STR1## in which Fa is the radical of an organic dye of the monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide series, T is a negative substituent, one X is a detachable substituent and the other X is a group of the formula ##STR2## A is arylene, V is hydrogen, a substituted or unsubstituted C.sub.1 -C.sub.4 alkyl radical or a radical of the formula --(CH.sub.2).sub.q --SO.sub.2 --Z, Z is a --CH.dbd.CH.sub.2 or CH.sub.2 --Y radical and Y is an inorganic or organic radical which is detachable under alkaline conditions, q, m and n are independently of one another an integral number from 2 to 6, R and R' are independently of one another hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl, and r is 1 or 2.
    Type: Grant
    Filed: March 28, 1988
    Date of Patent: November 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Karl Seitz, Karl Hoegerle
  • 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: 4963659
    Abstract: Reactive dyes which are particularly suitable for the dyeing or printing of cellulose-containing fiber materials by the exhaust process or by the continuous process and give, at a high color yield, dyeings and prints having good fastness properties, having the formula ##STR1## in which D.sub.1 and D.sub.2, independently of one another, are each a radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye; R.sub.1, R.sub.2, B.sub.1 and B.sub.2, independently of one another, are hydrogen or alkyl having 1 to 4 carbon atoms, which is unsubstituted or substituted by halogen, hydroxyl, cyano, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato; X is fluorine, chlorine, bromine, sulfo, C.sub.1 -C.sub.
    Type: Grant
    Filed: March 14, 1989
    Date of Patent: October 16, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanassios Tzikas
  • Patent number: 4960870
    Abstract: The heavy metal complex dyes of azo or azomethine dyes of the formula ##STR1## in which D is the radical of a dizao component of the benzene, naphthalene or heterocyclic series, K--OH is the radical of the formula ##STR2## in which the symbols A, A', B and B' each represent a carbon atom or in which one of the symbols A, A', B or B' represents a nitrogen atom while the others represent a carbon atom, R is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 alkyl or substituted or unsubstituted phenyl, and the ring E can be further substituted, Y is a nitrogen atom or a CH group, and n is 0 or 1, and in which --(CO).sub.n --OH is bonded to D in a position adjacent to --N.dbd.Y--, produce dyeings having good fastnesses particular very good crock, wet, wet crock and light fastness on nitrogen-containing or hydroxyl-containing fibre materials.
    Type: Grant
    Filed: February 1, 1988
    Date of Patent: October 2, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Urs Lehmann
  • 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: 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: 4925927
    Abstract: Reactive dyes which are particularly suitable for dyeing or printing cellulose-containing fiber materials by the exhaust method or by continuous methods having the formula ##STR1## in which D and D' are each independently of the other a radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye, R', R", B.sub.1 and B.sub.2 are independently of each other hydrogen or alkyl which has 1 to 4 carbon atoms and which is unsubstituted or substituted by halogen, hydroxyl, cyano, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato, X and Y are independently of each other fluorine, chlorine, bromine, sulfo, C.sub.1 -C.sub.4 -alkylsulfonyl or phenylsulfonyl, B is a direct bond or a radical --CH.sub.2).sub.n or --O--CH.sub.2).sub.n, n is 1 to 6; R is a radical of the formula ##STR2## Z is .
    Type: Grant
    Filed: June 27, 1988
    Date of Patent: May 15, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanassios Tzikas
  • Patent number: 4925928
    Abstract: Reactive dyes suitable in particular for dyeing or printing cellulose-containing fiber materials by the exhaust method or by continuous methods and, while giving a high dyeing yield, produce dyes and prints having good fastness properties; having the formula ##STR1## in which D is the radical or a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thiozanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye, R, 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 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato, X and Y independently of each other are fluorine, chlorine, bromine, sulfo C.sub.1 -C.sub.4 alkylsulfonyl or phenylsulfonyl, A is an amino substituent which contains at least one group of the formula--SO.sub.2 --Z(2)z is .beta.
    Type: Grant
    Filed: June 23, 1988
    Date of Patent: May 15, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanassios Tzikas
  • 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: 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: 4900812
    Abstract: Compounds of the formula ##STR1## and water-soluble salts thereof each cation of which is independently a non-chromophoric cation, whereinMe is cobalt, copper or nickel,Pc is the phthalocyanine radical,each R.sub.1 and R.sub.2 is independently hydrogen or C.sub.1-6 alkyl,each R.sub.4 is independently hydrogen, halo, hydroxy, C.sub.1-4 alkoxy, C.sub.1-4 alkyl, carboxy or sulfo,each R.sub.6 is hydrogen, cyano, carbamoyl or ##STR2## wherein An .crclbar. is a non-chromophoric anion,each R.sub.7 is hydrogen, C.sub.1-4 alkyl, C.sub.5-6 cycloalkyl, phenyl, benzyl, phenylethyl or carboxy,each W is linear or branched C.sub.2-6 alkylene; linear or branched C.sub.3-6 alkylene monosubstituted by hydroxy; linear or branched C.sub.2-6 alkylene interrupted by ##STR3## wherein R.sub.11 is linear or branched C.sub.
    Type: Grant
    Filed: January 29, 1988
    Date of Patent: February 13, 1990
    Assignee: Sandoz Ltd.
    Inventors: Helmut A. Moser, Roland Wald
  • 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: 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: 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