Plural Azo Groups In The Same Azo Moiety Attached Indirectly To Each Other By Nonionic Bonding Patents (Class 534/699)
  • Patent number: 6930178
    Abstract: The present invention relates to novel 1:2 chromium complex dyes, processes for their preparation and their use for dyeing or printing fiber materials containing hydroxyl groups or containing nitrogen. The present invention relates to a 1:2 chromium complex dye of formula (I): wherein all substituents are as defined in the claims, a process for their preparation and their use for dyeing or printing fiber materials containing hydroxyl groups or containing nitrogen.
    Type: Grant
    Filed: September 26, 2002
    Date of Patent: August 16, 2005
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Rainer Nusser, Georg Schoefberger, Reinhard Pedrazzi
  • Patent number: 5229502
    Abstract: A process is described for the preparation of pure, asymmetric 1:2 chromium complex dyes containing at least two groups which impart solubility in water, which process comprises reacting a mixture of two dyes of the formulaeF.sub.1 --(SO.sub.3 H).sub.t (1)andF.sub.2 --SO.sub.2 --Y (2)in which the symbols are as defined in claim 1 with a chromium donor in a molar ratio of 0.85:1.0 to 1.2:1.0 in a one-pot process under pressure at a temperature above 100.degree. C. and at a pH between 0 and 2 and then continuing the reaction at a slightly acid, neutral or slightly alkaline pH. The dyes obtained by the process according to the invention are suitable for dyeing, in particular, wool, silk, leather and synthetic polyamide fibres.
    Type: Grant
    Filed: February 21, 1990
    Date of Patent: July 20, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Gerhard Back, Alois Puntener
  • Patent number: 4997917
    Abstract: The invention relates to a process for the preparation of asymmetrical 1:2 chromium complex dyes of not less than 90% purity and containing at least one water-solubilizing group, which process comprises reacting a mixture of two metallizable azo dyes that contain different diazo components and different coupling components, or a mixture of a metallizable azo dye and a metallizable azomethine dye, in the molar ratio of 0.85:1.0 to 1.2:1.0, with the proviso that only one of said two mixture components contains at least one water-solubilizing group, with a chromium donor, under pressure and at a temperature above 100.degree. C. and in the pH range from 0 to 2, and subsequently carrying out further reaction in a weakly acid, neutral or weakly alkaline pH range, utilizing a single vessel for all steps.The dyes obtained by the process of the invention are particularly suitable for dyeing wool or polyamide materials.
    Type: Grant
    Filed: March 4, 1985
    Date of Patent: March 5, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Walter Iff, Daniel Parisot, Hans Schaller
  • Patent number: 4933437
    Abstract: The invention relates to a process for the preparation of asymmetrical 1:2 chromium complex azo dyes of not less than 90% purity and containing at least one water-solubilizing group, which process comprises reacting a mixture of two metallizable azo dyes that contain identical diazo components or identical coupling components, in the molar ratio of 0.85:1.0 to 1.2:1.0, with the proviso that only one of said two azo dyes contains at least one water-solubilizing group, with a chromium donor, under pressure and at a temperature above 100.degree. C. and in the pH range from 0 to 2, and subsequently carrying out further reaction in a weakly acid, neutral or weakly alkaline pH range, utilizing a single vessel for all stepsThe dyes obtained by the process of the invention are particularly suitable for dyeing wool or polyamide materials.
    Type: Grant
    Filed: March 23, 1987
    Date of Patent: June 12, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Walter Iff, Daniel Parisot, Hans Schaller
  • Patent number: 4923973
    Abstract: 1:2 Cobalt complex dyes of the general formula I ##STR1## in which X.sub.1 is nitro or hydrogen, X.sub.2 is nitro, hydrogen, chlorine or methyl, Y.sub.1 is nitro or hydrogen, Y.sub.2 is nitro, hydrogen, chlorine or methyl, m and n, independently of each other, are each 1, 2 or 3, and Ka.sup.+ is a cation, and one of each pair of substituents X.sub.1 or X.sub.2 and Y.sub.1 or Y.sub.2 is nitro and the other is as defined but not nitro are especially suitable for dyeing wool or polyamide and, in particular, leather.
    Type: Grant
    Filed: July 17, 1989
    Date of Patent: May 8, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Alois Puntener
  • Patent number: 4874849
    Abstract: Dyes suitable for dyeing wool, polyamide and leather in orange, brown or olive-brown shades are disclosed, the dyes having the formula ##STR1## wherein A and D are each independently of the other a benzene or napththalene radical of a diazo component, which component carries the hydroxyl or carboxyl group in the ortho-position to the azo group;B is the radical of a coupling component which carries the group X adjacent to the azo group;X is oxygen or a radical of the formula --R--, in which R is hydrogen or C.sub.1 -C.sub.4 alkyl;Y is a radical of the formula ##STR2## in which formulae R.sup.1 and R.sup.5 are each independently of the other hydrogen or sulfo, R.sup.4 is hydrogen or nitro, R.sup.6 is hydrogen, methyl, methoxy or chlorine and R.sup.2 and R.sup.3 are each independently of the other hydrogen, halogen, nitro or sulfo;Ar.sup.1 is a benzene or napththalene radical which is unsubstituted or substituted by halogen, nitro, sulfo, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.
    Type: Grant
    Filed: December 19, 1986
    Date of Patent: October 17, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Gerhard Back, Fabic Beffa, Ulrich Schlesinger, Alois Puntener
  • Patent number: 4820309
    Abstract: Complexes of the formula ##STR1## wherein each R.sub.1 is independently (a) the radical of a coupling component of the active methylene non-cyclic or homocyclic series, (b) the radical of a coupling component of the heterocyclic series or (c) the radical of a coupling component of the monocyclic benzene series,with the proviso that at least one R.sub.1 is the radical of a coupling component of the active methylene non-cyclic or homocyclic series,each R.sub.2 is independently hydrogen, C.sub.1-4 alkyl or --SO.sub.2 NR.sub.4 R.sub.5,each R.sub.3 is independently hydrogen, halo, C.sub.1-4 alkyl or --SO.sub.2 NR.sub.4 R.sub.5, andeach M and M.sub.1 is independently hydrogen or a cation,wherein each R.sub.4 is independently hydrogen, C.sub.1-4 alkyl or C.sub.2-3 hydroxyalkyl, andeach R.sub.5 is independently hydrogen, C.sub.1-4 alkyl, C.sub.2-3 hydroxyalkyl, cyclohexyl, cyclohexyl substituted by methyl, phenyl or phenyl substituted by methyl, with the proviso that at least one of Ring A and R.sub.
    Type: Grant
    Filed: March 3, 1988
    Date of Patent: April 11, 1989
    Assignee: Sandoz Ltd.
    Inventor: Herbert Holliger
  • Patent number: 4680385
    Abstract: Metal complex dyes that produce level, fast dyeings on textile materials are provided according to the formula ##STR1## wherein: D is a benzene, naphthalene or heterocyclic radical of a diazo component;Y is nitrogen or --CH;K is the radical of a coupling component if Y is nitrogen, or an o-hydroxyaldehyde radical if Y is --CH;Ka is a cation;Me is chromium or cobalt;Z.sub.1 is --O-- or --COO-- ortho to N.dbd.YZ.sub.2 is --O-- or --NR vicinal to N.dbd.Y, wherein R is hydrogen or a C.sub.1 -C.sub.4 alkyl or phenyl radical;R.sub.1 is a direct bond or a C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkenyl, or aryl radical or heterocyclic radial containing 1 to 3 sulfur, oxygen or nitrogen atoms;R.sub.2 is hydrogen or C.sub.1 -C.sub.8 -alkyl or aryl radical;R.sub.3 is hydrogen or a C.sub.1 -C.sub.8 alkyl, aryl or amino radical, or a heterocyclic radical containing 1 to 3 sulfur, oxygen or nitrogen atoms;V is a direct bond or oxygen;Q is oxygen or sulfur; andw is 0 or 1.
    Type: Grant
    Filed: March 28, 1985
    Date of Patent: July 14, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Gerhard Back
  • Patent number: 4678851
    Abstract: Metal complex dyes that produce level, fast dyeings on textile materials are provided according to the formula ##STR1## wherein: D is a benzene, naphthalene or heterocyclic radical of a diazo component;Y is nitrogen or --CH;K is the radical of a coupling component if Y is nitrogen, or an o-hydroxyaldehyde radical if Y is --CH:Ka is a cation;Me is chromium or cobalt;Z.sub.1 is --O-- or --COO-- ortho to N.dbd.YZ.sub.2 is --O-- or --NR vicinal to N.dbd.Y, wherein R is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl or phenyl;X is a fiber reactive radical bound directly to or through an amino or amino-containing group to the complex;R.sub.1 is a direct bond or substituted or unsubstituted C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkenyl, or aryl radical or heterocyclic radical containing 1 to 3 sulfur, oxygen or nitrogen atoms;R.sub.2 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.8 -alkyl or aryl;R.sub.3 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.
    Type: Grant
    Filed: March 28, 1985
    Date of Patent: July 7, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Gerhard Back, Hans U. Schutz, Ulrich Schlesinger
  • Patent number: 4665162
    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: June 18, 1985
    Date of Patent: May 12, 1987
    Assignee: Sandoz Ltd.
    Inventors: Paul Doswald, Emil Moriconi, Helmut Moser, Horst Schmid
  • Patent number: 4661587
    Abstract: Disclosed are chrome complex dyes of the formula ##STR1## and of the formula ##STR2## wherein Z and Z' independently of one another are each nitrogen or --CH--;X and X' independently of one another are each oxygen, or a group of the formula --NR--, in which R is hydrogen or C.sub.1 -C.sub.4 -alkyl, provided X is oxygen when Z is --CH-- and provided X' is oxygen when Z' is --CH--;A and B independently of one another are each a diazo component of a benzene or naphthalene radical which carries the hydroxyl or carboxyl group in the o-position with respect to the azo group;C and D independently of one another are each a benzene or naphthalene radical which carries in the o-position with respect to the azo or azomethine group a hydroxyl or carboxyl group, or the radical of an aliphatic or cycloaliphatic aminocarboxylic acid, if n.sub.2 or n.sub.
    Type: Grant
    Filed: May 3, 1985
    Date of Patent: April 28, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Ulrich Schlesinger, Fabio Beffa
  • Patent number: 4652631
    Abstract: 1:2 chromium complex dyes suitable for dyeing nitrogen-containing materials and materials which contain hydroxyl groups, are disclosed which, in the form of the free acid, have the formula ##STR1## wherein each of the symbols independently has the following meanings: Z is nitrogen or a --CH,A is a benzene or naphthalene radical which carries the hydroxyl or carboxy ortho to the azo or azomethine group, or, if n is 1 and Z is a --CH, is the radical of an aliphatic, cycloaliphatic or aromatic aminocarboxylic acid,B and D are each independently of the other the radical of a coupling component which couples in the alpha- or o-position relative to X if Z is nitrogen, or the radical of an o-hydroxyaldehyde if Z is --CH,X is oxygen or --NR, wherein R is hydrogen or C.sub.1 -C.sub.4 alkyl, with the proviso that X must be oxygen if Z is --CH,Y is a bridge member of the formula --SO.sub.2 or --SO.sub.2 --NR--SO.sub.2 --, wherein R is hydrogen or C.sub.1 -C.sub.4 alkyl,n is 0 or 1, andp is an integer from 0 to 6.
    Type: Grant
    Filed: March 28, 1985
    Date of Patent: March 24, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Fabio Beffa, Ulrich Schlesinger
  • Patent number: 4582896
    Abstract: Dyes of the formula ##STR1## in which Me is cobalt or chromium, A is a diazo component of a benzene or naphthalene which carries a hydroxyl or carboxyl group in the o-position relative to the azo group, B is an o-aminonaphthol, R and R' independently of each other are each benzene or naphthalene which can carry further substituents, but no arylamino radicals, no sulfo groups and no metallizable groups, in the o-position relative to the azo group, Ka is a cation, p is 0 or 1, m and n independently of each other are each such a number from 0 to 1 that the total n+m is a number from 1 to 2, and q is an integer from 1 to 6 are particularly suitable for dyeing wool or polyamide and especially leather in shades of deep brown, grey and black.These dyes exhibit good affinity, good acid and alkali stability, and good fastness.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: April 15, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Gerhard Back
  • Patent number: 4502860
    Abstract: Dyes of the formula I ##STR1## in which A, B, C, D, E, F, Z, Z', X, X', n, n.sub.1, n.sub.2 and n.sub.3, p and Ka.sup..sym. are as defined in claim 1, are particularly suitable for dyeing wool or polyamide and especially leather.
    Type: Grant
    Filed: June 20, 1983
    Date of Patent: March 5, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Gerhard Back