Pyrazole Containing (including Hydrogenated) Patents (Class 534/636)
  • Patent number: 4975530
    Abstract: Intermediates useful for the preparation of fiber-reactive dyes having the formula ##STR1## in which Q is phenyl unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, nitro, cyano, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylsulfonyl, sulfo or trihalomethyl; 1- or 2-naphthyl; or unsubstituted or C.sub.1 -C.sub.4 alkyl, nitro, cyano, C.sub.1 -C.sub.4 alkoxycarbonyl or C.sub.1 -C.sub.4 alkylthio substituted furanyl, thienyl, thiazolyl, oxazolyl, isothiazolyl, benzothiazolyl, benzoisothiazolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl or 1,3,5-triazinyl, and A.sub.1 and A.sub.2 independently of one another are a radical of the formula ##STR2## in which R.sub.1 and R.sub.2 independently of one another are hydrogen; C.sub.1 -C.sub.4 alkyl unsubstituted or substituted by hydroxyl, sulfo, sulfato, carboxyl, cyano, halogen, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.
    Type: Grant
    Filed: November 22, 1989
    Date of Patent: December 4, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Kurt Burdeska
  • 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: 4955987
    Abstract: The invention describes a process for the preparation of concentrated aqueous, substantially salt-free solutions of aminotriazinyl reactive dyes, which process comprises starting from a dye which contains sulfo groups and one or more radicals capable of reaction with cyanuric halide, said dye being at least partly in the form of the ammonium salt, reacting said dye with cyanuric halide, in the presence of lithium hydroxide, and deionizing and concentrating the salt-containing synthesis solution by a membrane separation process.The so prepared mixed lithium/ammonium salts of the acid aminotriazinyl reaction dyes are readily water soluble and are suitable for the preparation of concentrated storage stable dye solutions.
    Type: Grant
    Filed: December 6, 1985
    Date of Patent: September 11, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Roger Lacroix, Edmond Ruhlmann
  • 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: 4931067
    Abstract: Method is set forth of dyeing a material comprising forming a solution having a basic salt of a water soluble dye of the formula: ##STR1## wherein n is 0 or 1;m is 0 or 1;m=1 when n=0;p=0 when m=1;p=1 when m=0;the subscripts 1 and 0 indicating, respectively, the presence and absence of the substituent subscripted;Y is CR.sub.2 COO, CR.sub.2 CR.sub.2 COO or CR.sub.2 CR.sub.2 CR.sub.2 COO;each R is independently hydrogen, methyl, ethyl, phenyl or phenyl substituted with methyl, ethyl, halo, cyano, ethynyl or nitro;G is CR, CR.sub.2 CR, CRCR.sub.2, CR.sub.2 CR.sub.2 CR, CR.sub.2 CRCR.sub.2 or CRCR.sub.2 CR.sub.2 ;E is OH, SH or NH.sub.
    Type: Grant
    Filed: March 27, 1987
    Date of Patent: June 5, 1990
    Assignee: SRI International
    Inventor: Ronald Swidler
  • Patent number: 4929719
    Abstract: Reactive dyes which are particularly suitable for dyeing and printing cellulose containing fiber materials by the cold padbatch process and which produce, in high dye yield, dyeings and prints having good fastness properties containing the radical of an amine of the formula ##STR1## in which R is hydrogen, halogen, hydroxyl or sulfo, Z is a radical of the formula --CH.dbd.CH.sub.2 or --CH.sub.2 --CH.sub.2 --Y, Y is a detachable group, R' is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by --COOH, --CN, --OH or --SO.sub.3 H, and E is a radical of the formula ##STR2## in which R' and Z are as defined above, alk, alk' and alk" independently of one another are a C.sub.1 -C.sub.6 alkylene radical, U is hydrogen, halogen, hydroxyl, sulfato, C.sub.1 -C.sub.4 alkanoyloxy, cyano, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, carbamoyl or a radical --SO.sub.2 --Z in which Z is as defined above, V is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.
    Type: Grant
    Filed: August 10, 1989
    Date of Patent: May 29, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Hansrudolf Schwander, Athanassios Tzikas, Peter Aeschlimann
  • Patent number: 4917705
    Abstract: The invention relates to a process for dyeing or printing natural or synthetic polyamide fiber materials which comprises dyeing or printing these fiber materials with reactive dyes of the formula ##STR1## where each M is a cation, R.sub.1 and R.sub.2 are independently of each other hydrogen or C.sub.1 -alkyl, and X.sub.1 and X.sub.2 are independently of each other .alpha.,.beta.-dibromopropionyl, .alpha.-bromoacryloyl, chloroacetyl or a mono-, di- or trihalopyrimidinyl radical.
    Type: Grant
    Filed: September 21, 1988
    Date of Patent: April 17, 1990
    Assignee: Ciba-Geigy Corp.
    Inventors: Dieter Mausezahl, Peter Loew
  • Patent number: 4918183
    Abstract: The invention relates to monoazo dyes of the formula ##STR1## wherein K is the radical of a coupling component of the benzene, naphthalene or heterocyclic series, and R is hydrogen, halogen, carboxy, a C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.2 -C.sub.6 alkanoylamino, C.sub.1 -C.sub.6 alkylsulfonylamino, C.sub.1 -C.sub.6 alkylsulfonyl, phenyl(C.sub.1 -C.sub.4)alkylsulfonyl or naphthyl(C.sub.1 -C.sub.4)alkylsulfonyl or benzoyl radical, which radicals may be further substituted, or is a ##STR2## group, wherein each of R.sub.1 and R.sub.2 independently of the other is hydrogen or a C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or naphthyl radical, which radicals may be further substituted, and wherein X is hydrogen, halogen or a C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.2 -C.sub.6 alkanoylamino or C.sub.1 -C.sub.6 alkylsulfonylamino radical, which radicals may be further substituted.These dyes give dyeings of good light- and wetfastness properties on polyamide material.
    Type: Grant
    Filed: October 24, 1985
    Date of Patent: April 17, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Hurter
  • Patent number: 4918169
    Abstract: Reactive dyes suitable for dyeing and printing cellulosic fiber materials by the cold pad-batch process having the formula ##STR1## wherein Fa is a monoazo or polyazo, metal complex azo, anthraquinone, phthalocyanine, formazane, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, napthoquinone, pyrenequinone or perylene-tetracarbimide dye radical, X is halogen, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl, a sulfonic acid or phosphonic acid group or a quaternized ammonium group, r is 1 or 2, R is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy or phenyl, and A is a radical of the formula ##STR2## wherein R' is hydrogen, C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy or phenyl, C.sub.5 -C.sub.
    Type: Grant
    Filed: August 19, 1988
    Date of Patent: April 17, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Karl Hoegerle
  • Patent number: 4916215
    Abstract: Water-soluble disazo compounds of the general formula ##STR1## in which D.sub.1 and D.sub.2 are each a phenylene or naphthylene radical which can be substituted by 1 or 2 substituents from the group consisting of 1 chlorine, 1 bromine, 2 sulfo, 2 carboxyl, 2 alkyl of 1 to 4 carbon atoms and 2 alkoxy of 1 to 4 carbon atoms, R' and R" each denote an amino or hydroxyl group, R.sup.+ and R* each represent methyl, carboxyl or lower carbalkoxy, R.sup.1 and R.sup.3 are each hydrogen, lower alkyl, lower alkoxy, chlorine or bromine, R.sup.2 and R.sup.4 each denote hydrogen, lower alkyl, lower alkoxy or chlorine, X denotes a vinyl, .beta.-sulfatoethyl,.beta.-thiosulfatoethyl or .beta.-chloroethyl group and Y is a chlorine, fluorine or bromine atom or a sulfo, hydroxyl, aliphatic or aromatic ether group or thioether group or a primary, secondary or tertiary amino group.
    Type: Grant
    Filed: March 29, 1988
    Date of Patent: April 10, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ernst Hoyer, Rudolf Fass
  • Patent number: 4908436
    Abstract: A reactive dye of the formula ##STR1## or of the formula ##STR2## or of the formula ##STR3## in which D, D.sub.1 and D.sub.2 are each phenylene or naphthylene unsubstituted or substituted by alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, carboxylic acylamino having 1 to 8 carbon atoms, amino, alkylamino having 1 to 4 carbon atoms, phenylamino, N,N-di-.beta.-hydroxyethylamino, N,N-di-.beta.-sulfatoethylamino, sulfobenzylamino, N,N-disulfobenzylamino, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy radical, alkylsulfonyl having 1 to 4 carbon atoms, trifluoromethyl, nitro, cyano, halogen, carbamoyl, N-alkylcarbamoyl having 1 to 4 carbon atoms in the alkyl radical, sulfamoyl N-alkylsulfamoyl having 1 to 4 carbon atoms, N-(.beta.-hydroxyethyl)-sulfamoyl, N,N-di-(.beta.-hydroxyethyl)-sulfamoyl, N-phenylsulfamoyl, ureido hydroxyl, carboxyl, sulfomethyl, or sulfo, R.sub.1 is hydrogen or C.sub.1-4 -alkyl unsubstituted or substituted by halogen, hydroxyl, cyano, C.sub.
    Type: Grant
    Filed: October 23, 1986
    Date of Patent: March 13, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Scheibli
  • Patent number: 4906737
    Abstract: Fibre-reactive dyes of the formula ##STR1## wherein X is an alkyl or alkoxy group of 1 to 4 carbon atoms, a carboxy group or a halogen atom, each of R.sub.1 and R.sub.2 is independently a hydrogen atom or an alkyl group of 1 to 4 carbon atoms and D is the radical of an organic dye which contains sulpho groups, and the benzene ring A can contain further substituents apart from X and SO.sub.3 H.
    Type: Grant
    Filed: August 17, 1988
    Date of Patent: March 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Herbert Seiler, Gert Hegar, Ester Hegar-Zimmerman
  • Patent number: 4906738
    Abstract: Water-soluble monoazo compounds of the general formula (1) ##STR1## in which D is a phenyl radical or naphthyl radical, either of which is substituted and mandatorily contains at least one group which imparts solubility in water and D is substituted, for example by 1, 2 or 3 substituents which can be selected from the set consisting of 1 sulfamoyl, 1 carbamoyl, 1 trifluoromethyl, 1 benzothiazol-2-yl, 1 sulfobenzothiazol-2-yl, 1 methylbenzothiazol-2-yl, 1 methylsulfobenzothiazol-2-yl, 1 styryl, 1 nitrostyryl, 1 sulfostyryl and 1 nitrosulfostyryl group and, preferably, three sulfo groups, two carboxy groups, two alkyl groups of 1-4 C atoms, two alkoxy groups of 1-4 C atoms, 1 bromine atom and two chlorine atoms and one or two groups of the formula --SO.sub.2 --Z with Z of the meaning below, and the group --SO.sub.2 --Z can also be bonded to one of the substituents and Z represents the .beta.
    Type: Grant
    Filed: April 15, 1985
    Date of Patent: March 6, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Folker Kohlhaas, Fritz Meininger, Hans H. Steuernagel
  • Patent number: 4900813
    Abstract: Novel reactive dyes particularly suitable for the dyeing and printing of cellulose-containing fiber materials which give, in combination with a high color yield, dyeings and prints having good fastness properties, said dyes having the formula ##STR1## in which D is the radical of a diazo component, Q is a substituted or unsubstituted phenyl or naphthyl radical or a substituted or unsubstituted aromatic heterocyclic radical and A.sub.1 and A.sub.2 independently of one another are a radical of the formula ##STR2## in which R.sub.1 and R.sub.2 independently of one another are hydrogen, substituted or unsubstituted C.sub.1 -C.sub.6 alkyl or substituted or unsubstituted aryl, or R.sub.1 and R.sub.2 together with the N atom form a further substituted or unsubstituted heterocyclic 5- or 6-ring, with the proviso that at least one of the radicals A.sub.1, A.sub.2 and D has a fiber-reactive group.
    Type: Grant
    Filed: June 23, 1988
    Date of Patent: February 13, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Kurt Burdeska
  • Patent number: 4897469
    Abstract: Azo reactive dyes of the aniline series for dye or printing fiber materials of the formula ##STR1## wherein K is the radical of a coupling component, and Z is a vinyl sulfonyl reactive group ortho- or para- to the azo bridge.
    Type: Grant
    Filed: April 1, 1988
    Date of Patent: January 30, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Eilingsfeld, Ruediger Iden
  • Patent number: 4876334
    Abstract: Reactive dyes of the formula ##STR1## in which D is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye, B.sub.1 and B.sub.2 are independently of each other hydrogen or alkyl which has 1 to 4 carbon atoms and which can be substituted by halogen, hydroxyl, cyano, C.sub.1-4 alkoxy, C.sub.1-4 alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato, X is fluorine, chlorine, bromine, sulfo, alkylsulfonyl having 1 to 4 C atoms or phenylsulfonyl, B is a --CH.sub.2 --.sub.n or --O--CH.sub.2 --.sub.n radical, n is 1 to 6, R is a radical of the formula ##STR2## Z is .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-acyloxyethyl, .beta.
    Type: Grant
    Filed: February 1, 1988
    Date of Patent: October 24, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Paul Herzig
  • Patent number: 4873320
    Abstract: Water-soluble dyes which contain one or two fiber-reactive groups of the formula ##STR1## in which each R is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, it being possible for both R to have a meaning which is identical to or different from one another, Y is the vinyl group or a group of the general formula --CH.sub.2 --CH.sub.2 --X in which X represents a substituent which can be eliminated as an anion, and m represents the number 2 or 3. These novel dyes can be used to dye hydroxy and/or carboxamide group-containing materials in particular fiber-materials, such as, in particular, cellulose fiber materials, in fast shades.
    Type: Grant
    Filed: December 15, 1987
    Date of Patent: October 10, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Springer, Manfred Kuhn, Holger M. Buch
  • Patent number: 4866164
    Abstract: The monoazo dyes of the formula ##STR1## wherein R.sub.1 is N-ethylanilino or anilino which is substituted by C.sub.2 -C.sub.5 alkanoylamino, R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl and R.sub.3 is halogen or C.sub.1 -C.sub.4 alkyl, produce dyeings and prints of good lightfastness and wetfastness properties on polyamide fibre materials.
    Type: Grant
    Filed: March 24, 1986
    Date of Patent: September 12, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Hurter
  • Patent number: 4855410
    Abstract: The invention relates to a process for the preparation of azo compounds of the formula ##STR1## wherein K is the radical of a coupling component, R is a water-solubilising group and X is a fibre-reactive radical, and the benzene ring A may be further substituted, which process comprises reacting a compound of the formula ##STR2## in an aqueous medium containing 5 to 25% by weight of an alkali metal halide or alkali metal sulfate, based on the weight of the medium, with a compound which introduces the radical X to give the compound of the formula ##STR3## diazotising said compound direct and coupling the diazotisation product with a coupling component of the formulaH--K (4)in which formulae (2), (3) and (4) A, R, X and K are as defined for formula (1).
    Type: Grant
    Filed: July 9, 1986
    Date of Patent: August 8, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Rudiger Oxenius, Charles Wilhelm
  • Patent number: 4843148
    Abstract: A process for the preparation of reactive dyes of the formula ##STR1## in which D, R and Z are as defined in greater detail in the description, which comprises subjecting 2,4,6-trifluoro-s-triazine to a condensation reaction in a strongly acid solution and in the presence of an alkali metal fluoride with an amine of the formulaH--Z (3)and then subjecting the primary condensation product obtained to a condensation reaction with an amino dye of the formula ##STR2## affords reactive dyes of the formula (1) in a high yield and a high state of purity.
    Type: Grant
    Filed: December 23, 1986
    Date of Patent: June 27, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Emil Bonometti, Herbert Seiler
  • Patent number: 4843150
    Abstract: A water soluble disazo colorant represented by formula (I) in the form of free acid: ##STR1## wherein K represents ##STR2## [wherein A represents a methyl group or a carboxylic group; R.sup.2 represents a hydrogen atom, an alkyl group of 1 to 8 carbon atoms, a sulfoalkyl grouop of 1 to 4 carbon atoms, or an alkyl group of 1 to 4 carbon atoms which is substituted by an alkoxy group of 1 to 4 carbon atoms;R.sup.3 represents a hydrogen atom, a halogen atom, a cyano group, a --CONH.sub.2 group, a carboxyl group, a sulfonic group, or a sulfomethyl group, p represents an integer of 1 or 2];Z represents a fluorine atom or ##STR3## [wherein R.sup.4 represents a hydrogen atom or an alkyl group of 1 to 4 carbon atoms;R.sup.5 and R.sup.6 each represents independently a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, a sulfonic group, or a halogen atom; Y represents --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.
    Type: Grant
    Filed: July 9, 1987
    Date of Patent: June 27, 1989
    Assignee: Mitsubushi Chemical Industries Limited
    Inventors: Toshio Hihara, Yukiharu Shimizu, Kanzi Shimizu
  • Patent number: 4843149
    Abstract: A monoazo compound, or a salt thereof, represented by the formula, ##STR1## wherein D is a sulfophenyl group substituted with a methyl, ethyl, methoxy, ethoxy, phenoxy, acetylamino, pripionylamino, benzoylamino, carboxybenzoylamino, maleinylamino or succinylamino group, a naphthyl group substituted with two or three sulfo groups of a group of the formula ##STR2## any one of X.sub.1 or X.sub.2 is a sulfo group and the other is a methoxy or ethoxy group, Y is a fluorine or chlorine atom or an arylamino group substituted with one or two sulfo groups, R is a hydrogen atom or an unsubstituted or substituted lower alkyl group, A is an unsubstituted or substitued phenylene or naphthylene group, and Z is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub..sub.2 CH.sub.2 Z.sub.1 in which Z.sub.1 is a group capable of being split by the action of an alkali, which is useful as a fiber-reactive dye for dyeing materials in a greenish yellow color excellent in various fastness properties.
    Type: Grant
    Filed: November 13, 1985
    Date of Patent: June 27, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yutaka Kayane, Hirokazu Sawamoto, Takashi Omura, Naoki Harada, Akira Takeshita
  • Patent number: 4841030
    Abstract: They are useful for dyeing and printing materials containing hydroxyl groups or amide groups.
    Type: Grant
    Filed: December 4, 1981
    Date of Patent: June 20, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventor: Horst Jager
  • Patent number: 4839468
    Abstract: Triazine compounds which in their betaine form correspond to the formula ##STR1## wherein Y denotes hydrogen or the radical of an azo dye-stuff,R denotes hydrogen or alkyl,Ar denotes arylene,Z denotes halogen, hydroxyl, alkoxy, alkyl, aryl or an amino group which may be monosubstituted or disubstituted,m denotes 0 or 1 andX.sup.(+) denotes an ammonium groupamd whereimthe cyclic and acyclic radicals can carry further substituents,are used for dyeing/coloring natural and synthetic substrates and compositions, in particular paper.
    Type: Grant
    Filed: November 13, 1984
    Date of Patent: June 13, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Nickel, Peter Wild, Frank-Michael Stohr
  • Patent number: 4808706
    Abstract: Dyes of the formula ##STR1## wherein D is the radical of an organic dye, R.sub.1 is hydrogen or methyl, R.sub.2 is alkyl of 2 to 4 carbon atoms, and X is hydrogen or methyl.
    Type: Grant
    Filed: February 14, 1984
    Date of Patent: February 28, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Herbert Seiler
  • Patent number: 4801694
    Abstract: Reactive dyes of the formula ##STR1## in which D is the radical of an organic dye of the monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthrone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide series, R is hydrogen or substituted or unsubstituted C.sub.1-4 -alkyl, X is a substituent which is detachable as an anion, B is a radical of the formula ##STR2## R.sub.1 and R.sub.2, independently of each other, are hydrogen or substituted or unsubstituted C.sub.1-4 -alkyl or phenyl, A is a substituted or unsubstituted aliphatic or aromatic bridge member, Y is a --CO--Z or --SO.sub.2 --Z radical, Z is an aliphatic, aromatic or heterocyclic reactive radical, and n is 1 or 2, are suitable for dyeing or printing cellulose-containing and nitrogen-containing materials and in high dyeing yield produce dyeings and prints having good fastness properties.
    Type: Grant
    Filed: July 13, 1987
    Date of Patent: January 31, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Scheibli, Karl Seitz, Herbert Seiler, Athanassios Tzikas
  • Patent number: 4786721
    Abstract: The reactive dyes are useful, in particular, for dyeing or printing cellulose-containing fiber materials by the cold pad-batch method and produce, with a high dyeing yield, dyeings and prints having good fastness properties.
    Type: Grant
    Filed: August 13, 1986
    Date of Patent: November 22, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Peter Aeschlimann, Paul Herzig
  • Patent number: 4785081
    Abstract: A new process for the production of reactive dyes by the reaction of cyanuric chloride with anionic dyes containing an amino group, which process comprises the adiabatic reaction of cyanuric chloride with the dye, at a temperature of 20.degree. to 80.degree. C. and a pH value of between 3.0 to 7.0, with the rapid addition of the educts within 1 to 30 minutes, produces reactive dyes in good yield and purity and is technically advantageous.
    Type: Grant
    Filed: September 22, 1986
    Date of Patent: November 15, 1988
    Assignee: Ciba-Geigy AG
    Inventor: Karlheinz Franke
  • Patent number: 4782140
    Abstract: The invention relates to novel useful reactive dyes of the formula I ##STR1## in which: F is a radical selected from the group consisting of metal-free or metal-containing monoazo or disazo dyes containing at least one --SO.sub.3 H group, anthraquinone dyes, sulfophthalocyanine dyes, formazan dyes, phenazine dyes, oxanine dyes and nitroaryl dyes,R is hydrogen, C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted with --COOH or --SO.sub.3 H, cyanoethyl, or hydroxyethyl, X is fluorine, chlorine, bromine, --SO.sub.3 H, phenylsulfonyl or C.sub.1 -C.sub.4 -alkylsulfonyl,P is 1 or 2 andA is a radical of the formula ##STR2## in which: the groups designated "alk" are independently of each other straight or branched polymethylene radicals having 2 to 6 carbon atoms, andZ is .beta.-halogenoethyl, vinyl, .beta.-sulfatoethyl, .beta.-thiosulfatoethyl or .beta.acetoxyethyl.
    Type: Grant
    Filed: October 2, 1986
    Date of Patent: November 1, 1988
    Assignee: Ciba-Giegy Corporation
    Inventor: Athanassios Tzikas
  • Patent number: 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: 4762916
    Abstract: Water-soluble compounds having fiber-reactive dye properties of the general formula ##STR1## in which A is an alkylene of 2 to 6 carbon atoms or a phenylene which can be substituted by 1 or 2 substituents, or is a radical of the formula ##STR2## in which W is a direct bond or a bridge member and the R' and R* each denote hydrogen, chlorine, methyl, methoxy, ethoxy, carboxy or sulfo;B is chlorine or fluorine;R is hydrogen, chlorine, an alkyl of 1 to 4 carbon atoms or an alkoxy of 1 to 4 carbon atoms;M is hydrogen or an alkali metal;n stands for the number zero, 1 or 2,K is a radical of the formula ##STR3## in which D is phenylene which can be substituted by chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, carboxy or sulfo, or is naphthalene with optionally 1 or 2 sulfo groups,R.sup.1 denotes hydrogen, chlorine, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms,R.sup.
    Type: Grant
    Filed: December 23, 1986
    Date of Patent: August 9, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ludwig Schlafer, Hartmut Springer, Michael Kunze
  • Patent number: 4754023
    Abstract: A reactive dye of the formula ##STR1## in which: F is a radical selected from the group consisting of metal-free or metal-containing monoazo or disazo dyes containing at least one --SO.sub.3 H group, anthraquinone dyes, sulfophthalocyanine dyes, formazan dyes, phenazine dyes, oxazine dyes and nitroaryl dyes,R is hydrogen, C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted with --COOH or --SO.sub.3 H, cyanoethyl, or hydroxyethyl,X is fluorine, chlorine, bromine, --SO.sub.3 H, phenylsulfonyl or C.sub.1 -C.sub.4 -alkylsulfonyl,p is 1 or 2 andA is a radical of the formula ##STR2## in which: Y is chlorine, bromine, fluorine, --OH, --OSO.sub.3 H, --O-acyl, --CN, --COOH, --COO--C.sub.1 -C.sub.4 -alkyl, --CONH.sub.2 or --SO.sub.2 --Z,the group designated "alk" is a straight or branched polymethylene radical having 2 to 6 carbon atoms,V is ##STR3## hydrogen or C.sub.1 -C.sub.4 -alkyl which is unsubstituted or substituted by C.sub.1 -C.sub.2 -alkoxy, carboxyl, sulfo, halogen or hydroxy,Z is .beta.
    Type: Grant
    Filed: January 23, 1986
    Date of Patent: June 28, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Herbert Seiler, Peter Scheibli
  • Patent number: 4731441
    Abstract: Water-soluble monoazo and disazo compounds having fiber-reactive dye properties which are suitable for dyeing carbamoyl- and hydroxyl-containing materials, in particular cellulose fiber materials, and containing as diazo components an optionally substituted phenyl radical or naphthyl radical or a phenylazophenyl, phenylazonaphthyl, naphthylazophenyl or naphthylazonaphthyl radical, one of these radicals containing bonded in the diazo component a vinylsulfonyl, .beta.-thiosulfatoethylsulfonyl, .beta.-phosphatoethylsulfonyl, .beta.-chloroethylsulfonyl or .beta.-sulfatoethylsulfonyl group, and as coupling component that of a naphthol, aminonaphthaline or aminobenzene having a fiber-reactive grouping of the general formula ##STR1## in which the two R.sup.1 s, identical to or different from each other, denote a hydrogen atom or an optionally substituted alkyl group of 1 to 4 carbon atoms, R is a hydrogen atom or a sulfo group and Y represents the vinyl group, a .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.
    Type: Grant
    Filed: March 19, 1986
    Date of Patent: March 15, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Marcos Segal, Michael Kunze
  • Patent number: 4709018
    Abstract: Reactive dyes of the formula ##STR1## in which D is the radical of an organic dye of the monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide series, R is hydrogen or substituted or unsubstituted C.sub.1-4 -alkyl, X is a substituent which is detatchable in the form of an anion, A is arylene or C.sub.2-6 -alkylene, Y is a --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --Z radical, Z is an inorganic or organic radical which is detachable under alkaline conditions, B is hydrogen or the radical of a substituted or unsubstituted hydrocarbon, T is a negative substituent, and n is 1 or 2, are suitable for dyeing or printing cellulose-containing and nitrogen-containing materials and produce, in high colouristic yields, dyeings and prints having good fastness properties.
    Type: Grant
    Filed: August 30, 1984
    Date of Patent: November 24, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Karl Seitz
  • 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: 4649193
    Abstract: Water-soluble fibre-reactive dyestuffs containing one or two fibre-reactive groups of the vinylsulfone series and one or two fibre-reactive groups of the fluoro-s-triazinyl-amino series. These dyestuffs can be applied on fibre materials containing hydroxy and/or carbonamide groups by known application and fixation techniques for fibre-reactive dyes to yield deep and fast dyeings on these materials.
    Type: Grant
    Filed: August 1, 1983
    Date of Patent: March 10, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Fritz Meininger, Joachim W. Otten, deceased, by Ursula Otten, heir, by Anna G. Rudolph nee Otten, heir
  • Patent number: 4626589
    Abstract: A compound of the formula, ##STR1## wherein D is an organic dye moiety, R.sub.1 and R.sub.2 are independently hydrogen or a substituted or unsubstituted lower alkyl group, R.sub.3 is hydrogen or a substituted or unsubstituted lower alkyl, phenyl or naphthyl group, X.sub.1 and X.sub.2 are independently hydrogen, halogen or a lower alkyl, cyano, carbamoyl, vinyl, .beta.-hydroxyethyl, .beta.-sulfoethyl, .beta.-sulfatoethyl, carboxyl, carboxylic acid ester or sulfonic acid group, and Z is appended to the above-defined D or R.sub.3 and stands for --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Y, in which Y is a group capable of being split by the action of an alkali, which is useful for dyeing hydroxyl or amido group-containing fiber materials with excellent build-up properties, thereby giving dyed products having excellent various fastness properties.
    Type: Grant
    Filed: February 7, 1985
    Date of Patent: December 2, 1986
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takashi Omura, Yutaka Kayane, Mikoto Takahashi, Tetsuya Miyamoto, Akira Takeshita, Naoki Harada, Katsumasa Otake
  • Patent number: 4623719
    Abstract: This invention relates to disazo dyestuffs for cellulose or cellulose-containing fibers represented by the formula: ##STR1## wherein R.sup.1 represents a hydrogen atom, a nitro group, a halogen atom, an alkyl group of 1 or 2 carbon atoms or an acetylamino group; R.sup.2 and R.sup.3 each represents a hydrogen atom, an alkyl group of 1 or 2 carbon atoms, and alkoxy group or an acetylamino group; Y.sup.1 and Y.sup.2 each represents a hydrogen atom or an alkyl group, and alkenyl group, a cyclohexyl group, an aryl group or an aralkyl group which group ma optionally be substituted by cyano, hydroxyl, lower alkoxy or dialkylamino, or NY.sup.1 Y.sup.2 represents a 5-membered or 6-membered nitrogen-containing heretocyclic ring formed by combination of Y.sup.1 and Y.sup.2, and the total carbon atoms in Y.sup.1 and Y.sup.2 is 18 or less.
    Type: Grant
    Filed: March 24, 1986
    Date of Patent: November 18, 1986
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Toshio Niwa, Kiyoshi Himeno, Toshio Hihara
  • Patent number: 4614818
    Abstract: A process for the preparation of dyes of the formula ##STR1## in which D is a dye radical and R.sub.1 and R.sub.2 independently of one another is hydrogen or C.sub.1-4 -alkyl, which comprises reacting cyanuric fluoride of the formula ##STR2## simultaneously with a dye of the formula ##STR3## and with an ammonium salt of an amine of the formulaH.sub.2 N--R.sub.2 (4)in a neutral to alkaline medium, to give dyes of the formula (1) as single compounds in good yields in one operation. The novel process has the advantage of being able to be carried out as a "one-pot process" in a closed reaction vessel so that the apparatus is simple and immission by cyanuric fluoride is excluded.
    Type: Grant
    Filed: January 18, 1983
    Date of Patent: September 30, 1986
    Assignee: Ciba Geigy Corporation
    Inventors: Rolf Deitz, Herbert Seiler
  • Patent number: 4560747
    Abstract: A process for producing granulates of water-soluble dyes by means of fluidized bed granulation, wherein there is added a granulating auxiliary having a softening point or softening range between 30.degree. and 150.degree. C. and consisting of(a) at least one compound of the formula IA--(CH.sub.2 CH.sub.2 O).sub.n --H (I)in which A is the group R--O-- or ##STR1## wherein R is an aliphatic or alicyclic hydrocarbon radical having 8 to 22 carbon atoms, R' is an aliphatic hydrocarbon radical having 8 to 22 carbon atoms, and n is 10 to 200, preferably 20 to 150, or(b) a mixture of a compound of the formula II ##STR2## in which m is 50 to 500, and x is 3 to 5, with a compound of the formula IIIR.sub.1 --NH--CO--NH--R.sub.1 (III),in which each R.sub.1 independently of the other is hydrogen or methyl, or(c) a mixture of a compound of the formula I with at least one compound of the formula II or III.
    Type: Grant
    Filed: October 20, 1980
    Date of Patent: December 24, 1985
    Assignee: Ciba Geigy Corporation
    Inventors: Beat Bruttel, Hansjorg Schneider, Werner H. Dorfel
  • Patent number: 4556707
    Abstract: The invention provides reactive dyestuffs of the formula ##STR1## wherein X is a fibre-reactive group of the triazine or pyrimidine series; R.sub.3 and R.sub.4 are each hydrogen; n is 0 or 1; and k is a pyridone or pyrimidone coupling component; the dyestuffs are particularly suitable for dyeing and printing natural and regenerated cellulose fibre materials and synthetic polyamide fibre materials.
    Type: Grant
    Filed: February 1, 1984
    Date of Patent: December 3, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hermann Henk
  • Patent number: 4544738
    Abstract: A dye of the formula ##STR1## wherein R.sup.1 is is fluorine, chlorine, bromine, methyl, ethyl, cyano, carboxyl, nitro, tribfluoromethyl, methylsulfonyl, phenylsulfonyl, acetyl, C.sub.1 -C.sub.4 alkoxy, phenoxy, chlorophenoxy or benzoyl; R.sup.2 is hydrogen, chlorine, bromine, methyl, ethyl, C.sub.1 -C.sub.4 alkoxy, benzthiazol-2-yl, 6-methylbenzthiazol-2-yl, acetylamino, carboxyl aminosulfonyl, or aminocarbonyl; R.sup.3 is hydrogen chlorine, bromine or methyl; R.sup.5 is hydrogen, methyl, methoxy or ethoxy; and X is fluorohydroxyphosphonyl or dihydroxyphosphonyl. The dye of the present invention is useful in the dyeing of cellulose-containing material, polyamides and leather. The high tinctorial strength of the dyes and the very good lightfastness and wetfastness properties of the dyeings are particularly noteworthy.
    Type: Grant
    Filed: September 24, 1980
    Date of Patent: October 1, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Baumann, Hermann Kaack
  • Patent number: 4540776
    Abstract: A metal free azo dyestuff of the formula ##STR1## in which K is the radical of a coupling component of pyridone, andR.sub.3 and R.sub.4 each independently is hydrogen; C.sub.1 -C.sub.6 -alkyl; C.sub.1 -C.sub.6 -alkyl substituted by OH, SO.sub.3 H, COOH or OSO.sub.3 H; phenyl; naphthyl; or phenyl or naphthyl substituted by SO.sub.3 H or COOH.
    Type: Grant
    Filed: May 9, 1984
    Date of Patent: September 10, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hermann Henk, Erich Kramer, Karl H. Schundehutte, Horst Nickel