Acyclic -c(=x)-, Wherein X Is Chalcogen, Attached Directly Or Indirectly To The Hetero Ring By Nonionic Bonding Patents (Class 534/612)
  • 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: 5541300
    Abstract: Trifunctional reactive dyestuffs of the formula ##STR1## a process for their preparation and their use, wherein D=the radical of a diazo component of the benzene or naphthalene series,K=the radical of a coupling component of the formula ##STR2## where the radical of the formula II and the azo group are linked to one another via the bond marked with *,X=a radical of the formula ##STR3## Z=a heterocyclic fibre-reactive radical which differs from X and the other substituents have the meaning given in the description.
    Type: Grant
    Filed: May 27, 1994
    Date of Patent: July 30, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Konrad Bootz, Eckhard Bock, Manfred Hoppe, Wolfram Reddig
  • Patent number: 5532345
    Abstract: Compounds of the formula ##STR1## in which the variables are as defined in the claims, which are suitable as fibre-reactive dyes for dyeing or printing widely varying fibre materials, are described.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: July 2, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Paul Herzig, Anton Andreoli
  • Patent number: 5488098
    Abstract: A monoazo compound of the following formula, ##STR1## wherein D is phenylene or naphthylene; X is halogeno, pyridinio or ##STR2## B is --OR.sub.3, --SR.sub.4, ##STR3## in which R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each hydrogen, alkyl, phenyl, naphthyl or benzyl, r is 0 or 1, and E is O, SO, SO.sub.2, CH.sub.2 or NR.sub.8, in which R.sub.8 is hydrogen or C.sub.1 -C.sub.4 alkyl; R, R.sub.1, R.sub.2 and R.sub.7 are each hydrogen or alkyl; A.sub.1, A.sub.2 and A.sub.3 are each phenylene, naphthylene or alkylene; Z.sub.1, Z.sub.2 and Z.sub.3 are each --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; and p is 0 or 1; which compound is useful for dyeing or printing fiber materials to obtain a product dyed or printed in a color superior in various fastness properties with superior build-up property.
    Type: Grant
    Filed: February 7, 1994
    Date of Patent: January 30, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masayuki Miki, Kingo Akahori, Yutaka Kayane, Takeshi Washimi
  • 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: 5484898
    Abstract: The invention relates to compounds of formula ##STR1## wherein the variables are as defined in the claims. The compounds are suitable for use as dyes, especially for dyeing and printing cellulosic fibre materials, and give dyeings and prints of good fastness properties.
    Type: Grant
    Filed: May 10, 1994
    Date of Patent: January 16, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Rolf Deitz, Athanassios Tzikas
  • Patent number: 5451666
    Abstract: A water-soluble dye having a reactive group of the Formula (1): ##STR1## wherein: R.sup.1 is H or optionally substituted alkyl;R.sup.2 is H or C.sub.1-4 -alkyl;L is a divalent organic spacer group; andV is vinyl or a group convertible to vinyl on treatment with aqueous alkali.The reactive dyes of the present invention are useful for coloring natural and artificial textile materials containing amino or hydroxyl groups.
    Type: Grant
    Filed: June 9, 1993
    Date of Patent: September 19, 1995
    Assignee: Zeneca Limited
    Inventor: Kenneth Anderton
  • Patent number: 5449762
    Abstract: Reactive dyes of the formula I ##STR1## where n is 0 or 1R.sup.1, R.sup.2 and R.sup.3 are in each case hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,R.sup.4 is fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl or a radical of the formula ##STR2## L is a bridge member, A is unsubstituted or substituted C.sub.2 -C.sub.8 -alkylene,Y is vinyl or a radical of the formula --CH.sub.2 --CH.sub.2 --Q, Q being a group which can be removed under alkaline reaction conditions, andD is phenyl or naphthyl, it being possible for these radicals to be substituted, and a process for preparing reactive dyes by oxidation of the abovementioned compounds are described.
    Type: Grant
    Filed: February 1, 1995
    Date of Patent: September 12, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Wiesenfeldt, Bernd Siegel, Manfred Patsch
  • Patent number: 5428140
    Abstract: Reactive dyes of the formula ##STR1## where n is 0 or 1R.sup.1, R.sup.2 and R.sup.3 are in each case hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,R.sup.4 is fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl or a radical of the formula ##STR2## L is a bridge member, A is unsubstitued or substituted C.sub.2 -C.sub.8 -alkylene,Y is vinyl or a radical of the formula --CH.sub.2 --CH.sub.2 --Q, Q being a group which can be removed under alkaline reaction conditions, andD is phenyl or naphthyl, it being possible for these radicals to be substituted,and a process for preparing reactive dyes by oxidation of the abovementioned compounds are described.
    Type: Grant
    Filed: June 6, 1994
    Date of Patent: June 27, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Wiesenfeldt, Bernd Siegel, Manfred Patsch
  • Patent number: 5420256
    Abstract: Reactive dyestuffs have the following formula ##STR1## in which D is the radical of an organic dyestuffB is a direct bond or a bridging member on a ring C atom of an aromatic-carbocyclic or on a ring C atom or N atom of an aromatic-heterocyclic ring in D,R.sub.a, R.sub.b, identical or different, are H, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkyl substituted by OH, CN, CO.sub.2 H, OSO.sub.3 H or SO.sub.3 H,U is Cl, F or a pyridinium radical which is unsubstituted or substituted by CO.sub.2 H, CONH.sub.2, SO.sub.3 H or C.sub.1 -C.sub.4 -alkyl,W is straight-chain or branched C.sub.1 -C.sub.6 -alkylene,Y is CH.dbd.CH.sub.2 or CH.sub.2 --CH.sub.2 --X, in whichX is a radical which can be eliminated by alkali,V is H, halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.3 -alkyl, CN, COOH, CONH.sub.2, SO.sub.3 H.
    Type: Grant
    Filed: January 27, 1993
    Date of Patent: May 30, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Thomas Eizenhofer, Wolfgang Harms, Karl-Josef Herd
  • Patent number: 5342927
    Abstract: Reactive dyestuffs of the formula ##STR1## in which X is ##STR2## and Z is a heterocyclic reactive group and the remaining groups have the meaning given in the description, are highly suitable for the dyeing and printing of hydroxyl- or amido-containing materials.
    Type: Grant
    Filed: July 21, 1992
    Date of Patent: August 30, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfram Reddig, Karl-Josef Herd
  • Patent number: 5328995
    Abstract: The compounds of the formula ##STR1## where the substituents are as defined in claim 1, are direct dyes for various substrates, in particular cellulosic fibre materials. They are high temperature resistant and therefore are particularly highly suitable for the one-bath, single-stage dyeing of polyester/cotton blend fabrics with a disperse dye for the polyester fibres under the dyeing conditions for polyester fibres.
    Type: Grant
    Filed: January 27, 1993
    Date of Patent: July 12, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Rudolf Schaulin, Urs Lauk
  • Patent number: 5306813
    Abstract: A compound which, in the free acid form, is of Formula (1): ##STR1## wherein: D is optionally substituted phenyl or optionally substituted naphthyl;K is optionally substituted phenylene or optionally substituted naphthylene;R.sup.1 and R.sup.4 are each independently H or optionally substituted alkyl;R.sup.2 and R.sup.3 are each independently H or optionally substituted alkyl, provided at least one of R.sup.2 and R.sup.3 is optionally substituted alkyl;B is H, optionally substituted alkyl or optionally substituted each A is H or a substituent; andeachA is H or a substituent; andL is an optionally substituted divalent organic radical. The compound is useful as a reactive dye for textiles.
    Type: Grant
    Filed: January 22, 1993
    Date of Patent: April 26, 1994
    Assignee: Imperial Chemical Industries PLC
    Inventors: Andrew H. M. Renfrew, John A. Taylor
  • Patent number: 5292870
    Abstract: A compound which, in the free acid form, is of Formula (1): ##STR1## wherein: Z is vinyl, or an ethyl group having a substituent at the 2-position which is capable of being eliminated in the presence of alkali to give a vinyl group;D is substituted or unsubstituted phenylene or naphthylene;K is the residue of a coupling component;R.sup.1 is H, alkyl or substituted alkyl;R.sup.2 is alkyl or substituted alkyl;X is halo or quaternary ammonium; andL is substituted or unsubstituted phenylene.The compound is useful as a dye for the coloration of, for example, cotton, on which it has excellent build up, good fixation efficiency and good wash off properties.
    Type: Grant
    Filed: November 8, 1991
    Date of Patent: March 8, 1994
    Assignee: Imperial Chemical Industries PLC
    Inventor: Kenneth Anderton
  • Patent number: 5286854
    Abstract: Basic azo dyes useful for dyeing or printing polymeric material have the formula ##STR1## where R.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkanoylamino,R.sup.2 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or a radical of the formula CO-X, andX is hydroxyl, C.sub.1 -C.sub.4 -alkoxy, amino, mono- or di(C.sub.1 -C.sub.6 -alkyl)amino or a radical of the formula ##STR2## where n is 0 or 1,R.sup.3, R.sup.4 and R.sup.5 are hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl,R.sup.6 is hydrogen or C.sub.1 -C.sub.4 -alkyl,L is C.sub.2 -C.sub.6 -alkylene, andAn.sup..crclbar. is one equivalent of an anion,with the proviso that at least one basic or quaternary radical is present in the molecule.
    Type: Grant
    Filed: December 30, 1992
    Date of Patent: February 15, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Erwin Hahn, Heidi Hengelsberg, Udo Mayer
  • Patent number: 5276148
    Abstract: Reactive dyes of the formula ##STR1## where n is 0 or 1,R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,A is unsubstituted or substituted C.sub.2 -C.sub.8 -alkylene,Y is vinyl or a radical of the formula --CH.sub.2 --CH.sub.2 --Q, whereQ is a group which can be eliminated under alkaline reaction conditions,D.sup.1 is phenyl or naphthyl, where these radicals may be substituted,D.sup.2 is phenylene or naphthylene, where these radicals may be substituted, andZ is a reactive radical,with the proviso thata) n is zero when D.sup.1 is substituted by unsubstituted or substituted phenylazo or by unsubstituted or substituted naphthylazo andb) the reactive radical Z is not devised from the triazine series when n is zero and D.sup.1 is dihydroxysulfonylphenyl or trihydroxysulfonylnaphthyl,are used for dyeing and printing organic substrates containing hydroxyl groups or nitrogen atoms.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: January 4, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Siegel, Manfred Patsch
  • Patent number: 5256774
    Abstract: Improved reactive dyestuffs have the following formula ##STR1## in which the substituents have the meaning given in the description.
    Type: Grant
    Filed: February 20, 1992
    Date of Patent: October 26, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Harms, Thomas Eizenhofer
  • Patent number: 5239063
    Abstract: Fiber reactive azo dyestuffs of the formula ##STR1## in which R=H or C.sub.1 -C.sub.6 alkyl, which can be substituted with OH, Hal, SO.sub.3 H or OSO.sub.3 H;Z=heterocyclic five or six membered ring;n, m=0, 1 or 2, wherein n+m=0, 1 or 2;Y=OH, OR, NR.sub.2 R.sub.3, OMe; andR.sub.2, R.sub.3, =H, R and R.sub.2, R.sub.3 and N can form a heterocyclic 5 or 6-membered ring.
    Type: Grant
    Filed: January 9, 1992
    Date of Patent: August 24, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Hoppe, Martin Michna, Karl-Josef Herd, Frank-Michael Stohr
  • Patent number: 5202436
    Abstract: The new triphendioxazine dyestuffs of the formula ##STR1## in which the substituents have the meaning given in the description are suitable for the dyeing and printing of cellulose-containing and amido-containing materials.
    Type: Grant
    Filed: March 7, 1991
    Date of Patent: April 13, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventor: Horst Jager
  • Patent number: 5182371
    Abstract: The reactive dyes have the formula ##STR1## where n is 0 or 1,R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,R.sup.4 is fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl or a radical of the formula ##STR2## L is a bridgemember, A is substituted or unsubstituted C.sub.2 -C.sub.8 -alkylene,Y is vinyl or a radical of the formula --CH.sub.2 --CH.sub.2 --Q, where Q is a group which is detachable under alkaline reaction conditions, andD is phenyl or naphthyl, which may each be substituted.The present dyes are useful in dyeing or printing hydroxyl- or nitrogen-containing fibres.
    Type: Grant
    Filed: February 14, 1992
    Date of Patent: January 26, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Siegel, Manfred Patsch
  • Patent number: 5116956
    Abstract: A polyazo compound of the following formula, ##STR1## wherein X is ##STR2## --NR.sub.2 R.sub.3, --OR.sub.4 or --SR.sub.5, in which R.sub.1 is hydrogen or alkyl, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each hydrogen, alkyl, phenyl, naphthyl or benzyl, A is phenylene, naphthylene or alkylene, Z is a fiber-reactive group of --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z' in which Z' is a splittable group, Y is pyridinio, and F is polyazo dye moiety carrying a fiber-reactive group like that represented by Z, which compound is useful for dyeing or printing fiber materials to obtain a product dyed or printed in a color superior in various fastness properties with superior build-up property.
    Type: Grant
    Filed: May 17, 1990
    Date of Patent: May 26, 1992
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Tetsuya Miyamoto, Kazufumi Yokogawa, Yutaka Kayane, Takashi Omura, Takeshi Washimi, Naoki Harada, Kingo Akahori
  • Patent number: 5104978
    Abstract: A monoazo compound represented by the following formula in the free acid form: ##STR1## wherein D is unsubstituted or substituted phenylene or naphthylene, X is unsubstituted or substituted pyridinio, Z is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 L in which L is a group capable of being split by the action of an alkali, and Y is --V--R in which V is --O-- or --S--, and R is hydrogen or which may be substituted alkyl, cyclohexyl, phenyl which may be substituted, naphthyl which may be substituted or benzyl which may be substituted, or ##STR2## in which R.sub.1 and R.sub.2 independently of one another are each hydrogen or unsubstituted or substituted alkyl, phenyl, naphthyl or benzyl, which is superior in solubility and useful for dyeing or printing fiber materials such as cellulose to a red color with superior build-up properties.
    Type: Grant
    Filed: November 20, 1989
    Date of Patent: April 14, 1992
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kingo Akahori, Masayuki Miki, Takashi Omura, Naoki Harada, Takeshi Washimi
  • Patent number: 5095102
    Abstract: Reactive dyestuffs of the formula ##STR1## in which A=H, halogen, alkyl, alkoxy, acylamino or amino,B=H, alkyl or alkoxy,X=--CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --Y, whereY=a radical which can be removed under alkaline conditions andZ=a fibre-reactive radical.
    Type: Grant
    Filed: August 13, 1990
    Date of Patent: March 10, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Josef Herd, Manfred Hoppe, Hermann Henk, Rolf Brockmann, Frank-Michael Stohr
  • Patent number: 5091516
    Abstract: Reactive dyes useful for dyeing or printing hydroxyl- or amino-containing organic substrates have the formula ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,R.sup.4 is C.sub.1 -C.sub.4 -alkoxy, phenoxy or a radical of the formula NL.sup.1 L.sup.2, where L.sup.1 and L.sup.2 are each substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or substituted or unsubstituted phenyl, or L.sup.1 and L.sup.2 together combine with the nitrogen atom joining them to form a heterocyclic radical, or L.sup.1 may also be hydrogen,R.sup.5 is fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl or a radical of the formula ##STR2## A is substituted or unsubstituted C.sub.2 -C.sub.8 -alkylene, Y is vinyl or a radical of the formula --CH.sub.2 --CH.sub.
    Type: Grant
    Filed: November 5, 1990
    Date of Patent: February 25, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Siegel, Manfred Patsch
  • Patent number: 5037965
    Abstract: A monoazo compound represented by the following formula in the free acid form, ##STR1## wherein D is phenylene or naphthylene, R is hydrogen or alkyl, A is phenylene or naphthylene, Z.sub.1 and Z.sub.2 independently of one another are each vinylsulfonyl, .beta.-sulfatoethylsulfonyl and the like, and X is pyridinio or amino represented by the following formula ##STR2## wherein R.sub.1 and R.sub.2 independently of one another are each hydrogen, alkyl, phenyl, naphthyl or benzyl, which is useful for dyeing or printing fiber materials to give dyed or printed products of red color excellent in fastness properties with excellent build-up, level-dyeing and washing-off properties.
    Type: Grant
    Filed: November 21, 1988
    Date of Patent: August 6, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshihiko Morimitsu, Kingo Akahori, Yutaka Kayane, Naoki Harada, Takashi Omura
  • Patent number: 5023326
    Abstract: Reactive dyes of the formula ##STR1## in which Y is hydrogen or sulfo, U is --CN, --CONH.sub.2, --SO.sub.3 H, --OH or --OSO.sub.3 H, D is a phenyl or naphthyl radical, which can be substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl and sulfo, and which contains at least one reactive radical bound direclty or via a bridge member to a ring carbon atom, or to which a further radical is bound which contains a reactive radical, and u is the number 2, 3, 4 or 5, are suitable in particular for the dyeing or printing of cellulose-containing fiber materials by the exhaust method or by the continuous method and product in combination with a high colorisitc yield dyeings and prints which have good fastness properties.
    Type: Grant
    Filed: November 9, 1989
    Date of Patent: June 11, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Herbert Seiler
  • Patent number: 4985545
    Abstract: A water-soluble formazan colorant, which is represented by the following general formula (I) in the form of free acid: ##STR1## (where: R represents a hydrogen atom or a lower alkyl group which may be substituted; X denotes a phenylene group or a naphthylene group which may be substituted; Y indicates --SO.sub.2 CH.dbd.CH.sub.2 group or --SO.sub.2 C.sub.2 H.sub.4 W group wherein W represents a group to be eliminated by the action of alkali; and Z designates a lower alkylamino group, a phenylamino group or a naphthylamino group, having one or two water-soluble groups selected from the group consisting of hydroxyl group, sulfonic acid group and carboxylic acid group); and a method of dyeing by use of the colorant. The colorant is used to dye cellulosic and nitrogen-containing fibers in blue shades with excellent reactive fixing properties.
    Type: Grant
    Filed: August 15, 1988
    Date of Patent: January 15, 1991
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Kiyoshi Himeno, Toshio Hihara, Kanzi Shimizu, Yukiharu Shimizu
  • Patent number: 4885360
    Abstract: Reactive dyes of the formula ##STR1## in which D is the radical of a 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.sub.1 and R.sub.2, independently of each other, are each hydrogen or the radical of an unsubstituted or substituted hydrocarbon, A is an unsubstituted or substituted aliphatic or aromatic bridge member, n is 0 or 1, Y is a --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --X radical, X is an inorganic or organic radical detachable under alkaline conditions, Z is a radical of the formula ##STR2## and Hal is chlorine or bromine, and if n is 1 Z must not be either of the two radicals mentioned at the end for Z, are suitable for dyeing or printing cellulose fibre materials and produce lightfast and wetfast dyeings or prints.
    Type: Grant
    Filed: November 21, 1988
    Date of Patent: December 5, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Scheibli
  • Patent number: 4847364
    Abstract: Methine-azo compounds of the formula ##STR1## in which A is the complement to a heterocyclic 5- or 6-membered ring which has a quaternized N atom as a ring member, which can contain further hetero atoms and which can be substituted or/and be fused with carbocyclic or heterocyclic rings,R is hydrogen, cyano or C.sub.2 --C.sub.3 -alkylene which is bonded to an N atom of ring A to form a 5- or 6-membered ring,B is substituted or unsubstituted phenylene or naphthylene,X.sup..crclbar. is an anion andKK is the radical of an open-chain coupling component which contains active methylene groups, except that, if A is the complement to a pyridinium ring, KK cannot be the radical of acetoacetanilide which is unsubstituted or alkyl-substituted in the aniline ring.They are suitable for use as dyes for dyeing and printing cationically dyeable substrates, in particular paper.
    Type: Grant
    Filed: June 16, 1987
    Date of Patent: July 11, 1989
    Inventor: Peter Mockli
  • Patent number: 4820806
    Abstract: Metal-free monoazo and disazo compounds of the formulaCH.sub.2 .dbd.CH--SO.sub.2 --W.sub.1 --D--N.dbd.N--K--(W.sub.2 --Z).sub.n,1:1 and 1:2 metal complexes of such metallizable metal-free compounds and acid addition salts of such metal-free compounds and 1:1 and 1:2 metal complexes, whereinD is the radical of a diazo component of the benzene, naphthalene or tetrahydronaphthalene series,K is the radical of a coupling component of the benzene, naphthalene, pyrazol-5-one, pyridine, pyridone, barbituric acid, quinoline, isoquinoline, benzeneazobenzene, benzeneazonaphthalene, naphthaleneazobenzene, naphthaleneazonaphthalene, tetrahydronaphthaleneazobenzene, tetrahydronaphthaleneazonaphthalene or acetoacetamide series,W.sub.1 is a direct bond or a divalent bridging radical,each W.sub.
    Type: Grant
    Filed: February 28, 1986
    Date of Patent: April 11, 1989
    Assignee: Sandoz, Ltd.
    Inventors: Werner Baumann, Joseph V. Diest, Herbert Eichenberger, Max Oppliger
  • Patent number: 4736021
    Abstract: There are described azo compounds of the formula ##STR1## wherein K is an optionally quaternized basic group,X is the radical COOR, in which R is an alkyl group or a substituted or unsubstituted phenyl group, or X is the radical CONHR', in which R' is an alkyl group or a substituted or unsubstituted phenyl group; and wherein the benzene rings B and/or D can be further substituted;and the use thereof as dyes for the dyeing of textile materials, and particularly for the dyeing of paper of all types, especially bleached, lignin-free, unsized paper.
    Type: Grant
    Filed: September 13, 1982
    Date of Patent: April 5, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Jean-Marie Adam, Pierre Galafassi
  • Patent number: 4686285
    Abstract: (i) Metal-free compounds of the formula ##STR1## (ii) tautomers thereof, (iii) 1:1 and 1:2 metal complexes of (i) and (ii),(iv) salts of (i), (ii), and (iii), and(v) mixtures of (i), (ii), (iii), and (iv),wherein the symbols are as defined in the Specification, are useful as dyes for, for example, polymers and copolymers of acrylonitrile, polyesters modified to contain acid groups, polyamides such as wool, leather, cotton, bast fibers such as hemp, flax, sisal jute, coir and straw, regenerated cellulose, glass fibers and paper (those wherein R.sub.o is other than hydrogen) or as intermediates for the synthesis of dyes.
    Type: Grant
    Filed: February 8, 1985
    Date of Patent: August 11, 1987
    Assignee: Sandoz Ltd.
    Inventor: Reinhard Pedrazzi
  • Patent number: 4670546
    Abstract: Compounds of the formula ##STR1## in metal-free, 1:1 or 1:2 metal complex form, or in acid addition salt form, where the symbols are defined in the specification, useful as dyes for, for example, regenerated cellulose, cotton, synthetic polyamides and polyesters modified to contain acid groups and polymers and copolymers of acrylonitrile and 1,1-dicyanoethylene.
    Type: Grant
    Filed: June 28, 1984
    Date of Patent: June 2, 1987
    Assignee: Sandoz Ltd.
    Inventors: Jacky Dore, Reinhard Pedrazzi
  • Patent number: 4664714
    Abstract: A pigment composition consisting of 100 parts by weight of a pigment, and from 0.1 to 30 parts by weight of a pigment dispersant of formula ##STR1## in which Q is (a) an anthraquinone dye or pigment radical, (b) an azo dye or pigment radical, (c) a benzimidazolone dye or pigment radical, (d) a phthalocyanine dye or pigment radical, (e) a quinacridone dye or pigment radical, (f) a dioxazine dye or pigment radical, (g) an anthrapyrimidine dye or pigment radical, (h) an anthanthrone dye or pigment radical, (i) an indanthrone dye or pigment radical, (j) a falvanthrone dye or pigment radical, (k) a pyranthrone dye or pigment radical, (l) a perinone dye or pigment radical, (m) a perylene dye or pigment or (n) a thioindigo dye or pigment radical; X is a direct bonds, --CH.sub.2 --; ##STR2## Y.sub.1 is NH or --O--; Z is in which Y.sub.2 is --NH-- or --O--, or --NH--X--Q when n is 1; R.sub.1 and R.sub.
    Type: Grant
    Filed: April 10, 1985
    Date of Patent: May 12, 1987
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Hiromitsu Katsura, Shigeyuki Ehashi, Motohiko Kashioka, Makoto Sakamoto
  • Patent number: 4656256
    Abstract: Compounds of the formula ##STR1## where Y is chlorine or bromine, Z is hydrogen, chlorine, bromine, a sulfonic ester group, nitro or unsubstituted or substituted sulfamyl, X is --O-- or ##STR2## R is alkylene which may or may not be interrupted by oxygen, ##STR3## m is 1 or 2, n is 0 or 1, p is 0, 1 or 2, q is 1 or 2, R.sup.1 and R.sup.2 independently of one another are each hydrogen, unsubstituted or substituted alkyl, alkenyl, cycloalkyl, aralkyl or aryl, or R.sup.1 and R.sup.2, together with the nitrogen atom, form a heterocyclic structure, R.sup.3 is hydrogen or unsubstituted or substituted alkyl, B is hydrogen or C.sub.1 -C.sub.4 -alkyl, B.sup.1 is hydrogen, hydroxyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkyl, A.sup.- is an anion, R.sup.4 is unsubstituted or substituted alkyl, R.sub.5 is hydrogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: May 16, 1985
    Date of Patent: April 7, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Colberg, Hans-Juergen Degen, Johannes P. Dix
  • Patent number: 4652632
    Abstract: Naphtholazo benzoylalkylene amines and salts thereof which are useful as dyes for acid-modified fibers, leather and paper, and which are represented by the formula ##STR1## wherein n is 0 or 1,A is an anion,R is C.sub.2 - to C.sub.4 -alkyleneR.sup.1 and R.sup.2 independently of one another are C.sub.1 - to C.sub.4 -alkyl, methoxyethyl, cyclohexyl, and R.sup.1 and R.sup.2 together are ##STR2## and R.sup.3 is methyl, ethyl or hydroxyethyl.
    Type: Grant
    Filed: April 1, 1985
    Date of Patent: March 24, 1987
    Assignee: BASF Aktiengesellschaft
    Inventor: Horst Colberg
  • Patent number: 4591635
    Abstract: Metal-free compounds and 1:1 and 1:2 metal complexes of the formula ##STR1## or a 1:2 metal complex of a metal-free compound of said formula and a metallizable azo compound not of said formula, whereineach K is independently a coupling component radical of the pyrazolone-5, 5-aminopyrazole, pyridone, 2,6-diaminopyridine, .beta.-naphthol, acetic acid ester, acetic acid amide or N-substituted N,N-disubstituted aniline series,each K.sub.1 is independently ##STR2## wherein R.sub.3 is hydrogen, C.sub.1-4 alkyl, phenyl or benzyl,R.sub.4 is C.sub.1-4 alkyl, (C.sub.1-4 alkoxy)-carbonyl or --CO--N(R.sub.8).sub.2, wherein each R.sub.8 is independently hydrogen or C.sub.1-4 alkyl,R.sub.5 is amino or hydroxy,R.sub.5a is hydroxy,T is hydrogen, cyano, ##STR3## or (C.sub.1-4 alkyl)carbonyl, wherein R.sub.7, R.sub.10, R.sub.12, Z.sub.a and A.crclbar. are as defined in the specification,each R.sub.1 is independently hydrogen, halo, hydroxy, C.sub.1-4 alkoxy or C.sub.1-4 alkyl, orR.sub.1 and R.sub.
    Type: Grant
    Filed: November 10, 1983
    Date of Patent: May 27, 1986
    Assignee: Sandoz Ltd.
    Inventors: Manfred Greve, Helmut Moser
  • Patent number: 4550158
    Abstract: Metal-free azo compounds of the formula ##STR1## wherein Ra is an aromatic group or an active methylene coupling component radical as defined in the specification,R.sub.t is an arylazo group or a group of the formula -Y-Z,whereinY is a direct bond or a bridging radical, andZ is a basic amino or quaternary ammonium group, ##STR2## wherein each of the variables is as defined above or below, X is a direct bond or a bridging radical,x is hydrogen, hydroxy C.sub.1-4 alkyl, C.sub.1-4 alkoxy, amino or carboxy,ring B is further unsubstituted or further substituted,d is 0, 1 or 2, andn is 0 or 1,with the provisos that (i) the compounds contain an average of at least 1.3 basic water-solubilizing groups, and (ii) the compounds are free of sulfo groups,and 1:1 and 1:2 metal complexes thereof,which metal-free compounds and metal complexes are useful as dyes for leather and paper.
    Type: Grant
    Filed: August 18, 1982
    Date of Patent: October 29, 1985
    Assignee: Sandoz Ltd.
    Inventors: Paul Doswald, Emil Moriconi, Helmut Moser, Horst Schmid
  • Patent number: 4525583
    Abstract: Benzthiazole compounds of the formula ##STR1## or a tautomeric form thereof, in which KK is the radical of a pyrimidine coupling compound as defined, W is a radical of the formula --CH.sub.2 --NH--CO--C.sub.1 --C.sub.4 -alkyl-Q.sup..sym. An.sup..crclbar. in which An is an anion and Q is a quaternary radical of the formula ##STR2## in which R.sub.1 to R.sub.6 independently of one another are a substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl radical, or the radicals R.sub.1 and R.sub.2, or R.sub.3 and R.sub.4, or R.sub.3 and R.sub.4 and R.sub.5, together with the N atom, form a heterocyclic ring, m is the number 1, 2 or 3 and n is the number 0 or 1, and in which the benzene radicals A, B and/or C may be further substituted are particularly suitable as dyes for paper, brilliant yellow to orange dyeings which have, in particular, good wet-fastness and light-fastness, being obtained.
    Type: Grant
    Filed: January 13, 1983
    Date of Patent: June 25, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Jean-Marie Adam
  • Patent number: 4486348
    Abstract: Cationic triazinyl dyestuffs of the formula ##STR1## wherein R.sub.11 and R.sub.12 independently of one another are H, Cl, Br, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.3 or C.sub.2 H.sub.5,X is a radical of the formula COCH.sub.3, CN, COOCH.sub.3, COOC.sub.2 H.sub.5, CONH.sub.2 or COC.sub.6 H.sub.5,Y and Z independently of one another are C.sub.2 -C.sub.5 -alkylene,R.sub.1 and R.sub.2 independently of one another are H, Cl, Br, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.3 or C.sub.2 H.sub.5,R.sub.3 and R.sub.4 independently of one another are hydrogen or C.sub.1 -C.sub.4 -alkyl,R.sub.5 -R.sub.10 independently of one another are hydrogen, C.sub.1 -C.sub.4 -alkyl, .beta.- or .gamma.-hydroxy-C.sub.2 -C.sub.4 -alkyl, phenyl or benzyl, orR.sub.5 and R.sub.6, and/or R.sub.8 and R.sub.9 in each case together with the nitrogen, form a pyrrolidine, morpholine or piperidine ring, orR.sub.5, R.sub.6 and R.sub.7 and/or R.sub.8, R.sub.9 and R.sub.
    Type: Grant
    Filed: February 24, 1984
    Date of Patent: December 4, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus Kunde