Amino Nitrogen Containing Patents (Class 534/725)
  • Publication number: 20100257678
    Abstract: Disclosed is an azo compound represented by the formula (1) below, a salt thereof, or a copper complex salt compound thereof. (In the formula, R1 and R2 independently represent a hydrogen atom, a sulfonic acid group, a lower alkyl group or a lower alkoxyl group; R3-R6 independently represent a hydrogen atom, a lower alkyl group or a lower alkoxyl group; R7 represents a lower alkyl group or a lower alkoxyl group; and n represents 0 or 1.
    Type: Application
    Filed: June 21, 2007
    Publication date: October 14, 2010
    Inventors: Yuichi Sadamitsu, Takahiro Higeta
  • Patent number: 6927284
    Abstract: 1:2-metal complex dyes of the formula wherein the symbols R1, R1?, R2, R2?, R3, R3?, Y, Z, n, n?, Me, M and (Kat)+ are defined as in the Claims, mixtures thereof, their compositions, their production and their use as anionic dyes for dyeing substrates, especially leather, in brown to red shades.
    Type: Grant
    Filed: October 14, 2002
    Date of Patent: August 9, 2005
    Assignee: Clariant Finance (BVI) Limited
    Inventor: Jordi Berenguer
  • Patent number: 6764524
    Abstract: Asymmetrical 1:2 chromium complex dyes of formula (I), wherein X signifies —SO3M, —SO2NR1R2 or chlorine, Y signifies hydrogen, —SO3M or chlorine, R1 signifies hydrogen, C1-6alkyl, C2-3-hydroxyalkyl or a radical of formulae (a) or (b), R2 signifies hydrogen, C1-6alkyl or C2-3-hydroxyalkyl, or R1 and R2 together with the nitrogen atom to which they are attached, form a 5- or 6-membered saturated heterocycle, R3 signifies hydrogen, C1-2-alkyl, chlorine, —COOM or —SO3M, R4 signifies hydrogen, C1-2-alkyl, C1-2-alkoxy chlorine or —SO3M, n signifies from 0 to 3, M signifies in each case hydrogen or a nonhromophoric cation, and M+signifies hydrogen or a nonchromophoric cation, are useful for dyeing artificially produced oxide layers on aluminium or aluminium alloys, on which they produce grey dyeings in high color yield and hue reproducibility
    Type: Grant
    Filed: September 28, 2000
    Date of Patent: July 20, 2004
    Assignee: Clariant Finance (BVI) Limited
    Inventor: Klaus Körte
  • Patent number: 6210448
    Abstract: 1:2 chromium complex dyes of the formula: in which R signifies C1-9-alkyl or a radical of the formula: R1 signifies C1-4-alkyl, R2 signifies hydrogen or —SO3M, R3 signifies hydrogen, methyl or methoxy, R4 signifies hydrogen, methyl, methoxy or chloro, n signifies from 0 to 3, M signifies hydrogen or a non-chromophoric cation and Kat+signifies hydrogen or a non-chromophoric cation, are suitable for dyeing artificially produced oxide layers on aluminium or aluminium alloys and so give rise to highly lightfast dyeings in yellow shades.
    Type: Grant
    Filed: November 24, 1999
    Date of Patent: April 3, 2001
    Assignee: Clariant Finance (BVI) Limited
    Inventor: Klaus Körte
  • Patent number: 5401834
    Abstract: Complexes of the formula ##STR1## which are in free acid or salt form, and mixtures thereof, wherein each ofR.sub.1 and R.sub.3 is independently hydrogen, C.sub.1-4 alkyl or C.sub.1-4 alkyl monosubstituted by hydroxy, amino, sulfo or carboxy,each ofR.sub.2 and R.sub.4 is independently hydrogen; C.sub.1-4 alkyl; C.sub.1-4 alkyl monosubstituted by hydroxy, amino, sulfo or carboxy; --COR.sub.5 ; --COOR.sub.6 or --CONHR.sub.7,M is chromium or cobalt, andM.sub.K.sup..sym. is hydrogen or a non-chromophoric cation, useful for dyeing or printing, materials such as natural and synthetic polyamides and particularly artificially produced oxide layers on aluminum and aluminum alloys.
    Type: Grant
    Filed: June 22, 1993
    Date of Patent: March 28, 1995
    Assignee: Sandoz Ltd.
    Inventor: Klaus Koerte
  • Patent number: 5189181
    Abstract: A process for the preparation of a polycyclic dye of the Formula (1): ##STR1## by reacting a substituted acetic acid of the Formula (2): ##STR2## with a compound of the Formula (3): ##STR3## and oxidation of the intermediate leuco compound to dehydrogenate the peripheral heterocyclic rings whereinY is an optionally substituted aromatic or heteroaromatic radical;Ring A is unsubstituted or is substituted by from one to five groups;Z is --NR.sup.1 R.sup.2 ;R.sup.1 and R.sup.2 are each independently H or are independently selected from optionally substituted alkyl, alkenyl, cycloalkyl, aralkyl, aryl and heteroaryl; orR.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached form a heterocyclic ring; orR.sup.1 and R.sup.2 each independently together with the nitrogen to which they are attached and the adjacent carbon atom of Ring B form a heterocyclic ring; andX.sup.1 and X.sup.
    Type: Grant
    Filed: January 7, 1992
    Date of Patent: February 23, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Nigel Hall, Nigel Hughes, Prakash Patel
  • Patent number: 4996303
    Abstract: The invention relates to a process for the preparation of 1:2 metal complex azo dyes of formula ##STR1## wherein each X is hydrogen, halogen or nitro, K and K' are each independently of the other the radical of a coupling component of the benzene, naphthalene or pyrazolone series, Y and Y' are each --O-- or --N(R), wherein R is hydrogen, C.sub.1 -C.sub.4 alkyl or phenyl, Me is chromium or cobalt and Ka is a cation, and Y and Y' are attached to K and K' adjacent to the azo group, by coupling and metallising, which process comprises coupling, in aqueous solution, a diazo component of formula ##STR2## wherein X is as defined for formula (1), in the presence of the 5- to 30-fold molar amount of sodium and/or potassium chloride, based on the molar amount of diazo component, and in the presence of a compound that donates a chromium or cobalt atom, to coupling components of formulaeHK--YH and HK'--Y'H (3),wherein K, K', Y and Y' are as defined for formula (1).
    Type: Grant
    Filed: November 22, 1988
    Date of Patent: February 26, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Alois Puntener, Daniel Parisot
  • 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: 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: 4748236
    Abstract: Reactive azo dyestuffs of the formula ##STR1## wherein D . . . radical of the benzene or naphthalene series, having a sulpho group in the o-position to the azo bridge,K . . . radical of a coupling component of the benzene, naphthalene, pyridone, pyrazolone or hydroxynaphthalene series, or an aryl-azo-aryl radical,R . . . hydrogen or C.sub.1 -C.sub.4 -alkyl,Y . . . OR.sub.1 or SR.sub.1, R.sub.1 representing an optionally substituted alkyl, aryl or heteroaryl radical, or NR.sub.2 R.sub.3, R.sub.2 representing hydrogen or an optionally substituted alkyl radical and R.sub.3 representing hydrogen or an optionally substituted alkyl or aryl radical, or R.sub.2 and R.sub.3 forming a ring, optionally with inclusion of a hetero-atom, andX . . . halogen, such as chlorine or fluorine and their use for dyeing and printing materials containing hydroxyl groups or containing amide groups.
    Type: Grant
    Filed: November 9, 1984
    Date of Patent: May 31, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Jager, Richard Schwaebel
  • Patent number: 4723001
    Abstract: The invention relates to chromium complexes of the formula ##STR1## in which B is the radical of a bidentate bianionic compound, L is H.sub.2 O, NH.sub.3, alkanol, alkylamine, dialkylamine, trialkylamine or pyridine, D is a benzene or naphthalene diazo component, Y is the nitrogen atom or the CH group, K is a coupling component, R is hydrogen, alkyl or phenyl, X is a fibre-reactive group,Ka is a cation, m is 1, 2 or 3, n is 1 or 2 and k is 0 or 1.These chromium complexes are suitable for dyeing nitrogen-containing or hydroxy-containing materials and they produce level dyeings having good all-round fastness properties.
    Type: Grant
    Filed: July 24, 1986
    Date of Patent: February 2, 1988
    Assignee: CIBA-GEIGY Corporation
    Inventors: Hans U. Schutz, Ulrich Schlesinger, Gerhard Back
  • Patent number: 4710198
    Abstract: A process of dyeing polyamide-containing material is disclosed using dyes of the following formula: ##STR1## wherein Me is cobalt or chromium,Ka.sup..sym. is a cation,p is 0 or 1,R and R' are each independently of the other hydrogen or a group of the formula --CO--(O).sub.n --Y, wheren is 0 or 1, andY is C.sub.1 -C.sub.5 alkyl, or phenyl which may be substituted by nitro, halogen, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy,with the proviso that R and R' may not both be hydrogen if p is 1.Novel dyes within this class are also disclosed. The process is especially useful for dyeing leather.
    Type: Grant
    Filed: December 9, 1985
    Date of Patent: December 1, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Fabio Beffa, Hans U. Schutz
  • Patent number: 4670486
    Abstract: High molecular weight organic material is effectively colored by the incorporation therein of a copper or nickel complex of the ligand compound of formula I ##STR1## wherein A is an isocyclic or heterocyclic aromatic moiety, R is H, halogen, lower alkyl or alkoxy, R.sub.1 is H, lower alkyl, phenyl or substituted phenyl, and B is H, lower alkyl, ureido or substituted ureido, guanidino, anilino, benzamido or a heterocyclic aromatic moiety.
    Type: Grant
    Filed: June 13, 1985
    Date of Patent: June 2, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Georg Cseh, Paul Lienhard
  • Patent number: 4667021
    Abstract: A chromium complex compound represented as the free acid form by the formula (I): ##STR1## wherein X.sup.1 represents a hydrogen atom, a methyl group, a methoxy group or a sulfonic acid group; X.sup.2, X.sup.3 and X.sup.4 represent independently a hydrogen atom, a chlorine atom, a methyl gorup, a methoxy group, a carboxyl group or a sulfonic acid group; Y represents a hydrogen atom or a sulfonic acid group; Z represents a chlorine atom, a fluorine atom or --N.sup.30 (R).sub.3 (R represents a C.sub.1 to C.sub.4 -alkyl group), ##STR2## and M represents a hydrogen atom or an alkali metal, a process for producing the chromium complex compound (I) and a method for dyeing cellulosic fibers with the same. The chromium complex compound represented by formula (I) is excellent in affinity to cellulosic fibers and in color-yield, build-up properties and fastness properties. These compounds are dyes for cellulosic fibers.
    Type: Grant
    Filed: September 26, 1984
    Date of Patent: May 19, 1987
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Junji Toda, Eiichi Ogawa
  • Patent number: 4650859
    Abstract: Chrome azo-azomethine dyes are disclosed which contain a benzthiazolylphenyl or stilbenyl radical bound via an aldehyde group to the aldehyde moiety of the azomethine dyes. The dyes are particularly useful for dyeing wool, polyamide and leather.
    Type: Grant
    Filed: December 31, 1984
    Date of Patent: March 17, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Fabio Beffa
  • Patent number: 4544739
    Abstract: Chromium complex dyes which, in the form of the free acid, have the formula ##STR1## wherein Z is hydrogen, nitro, chlorine or naphthylazo or phenylazo, wherein naphthyl or phenyl is unsubstituted or substituted by nitro, chlorine, bromine, C.sub.1-5 -alkyl or C.sub.1-5 -alkoxy, A is naphthyl or phenyl containing the oxygen atom in o-position to the azomethine and wherein naphthyl or phenyl is unsubstituted or substituted by C.sub.1-5 -alkyl, halogen or naphthylazo or phenylazo wherein naphthyl or phenyl is unsubstituted or substituted by nitro, chlorine, bromine, C.sub.1-5 -alkyl or C.sub.1-5 -alkoxy, D is sulfophenyl which is unsubstituted or substituted by nitro or chlorine, or sulfonaphthyl which is unsubstituted or substituted by nitro, and is bonded to the azo group in the ortho-position to the oxygen atom and R is chloroacetyl, bromoacetyl, .alpha.-chloroacryloyl, .alpha.-bromoacryloyl, .alpha.,.beta.-dichloropropionyl, .alpha.,.beta.
    Type: Grant
    Filed: September 28, 1982
    Date of Patent: October 1, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans U. Schutz, Arthur Buhler