Azo Moiety And Moiety Which Contains Acyclic -ch=n- Group Bonded To The Same Metal Patents (Class 534/695)
  • Patent number: 4775747
    Abstract: Transition metal complexes of the compounds of the formulae I and II ##STR1## in which A is an isocylic or heterocyclic aromatic radical, R is --H, halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, R.sub.1 is --H, C.sub.1 -C.sub.4 -alkyl or phenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, --NO.sub.2, --CONH.sub.2, --CONHR.sub.2 or C.sub.2 -C.sub.5 -N-alkylcarbamoyl, X is --CH.dbd. or --N.dbd. andB is --H, C.sub.1 -C.sub.4 -alkyl, --NHCONH.sub.2, --NHCONH-C.sub.1 -C.sub.4 -alkyl, --NHCONR.sub.2, --NHCSNH.sub.2, --NHCSR.sub.3, --NHC(NH)NH.sub.2, --NHR.sub.2, --NHCOR.sub.3, --NHSO.sub.2 R.sub.3 or a heterocyclic aromatic radical, and R.sub.2 and R.sub.3 are phenyl or substituted phenyl, are suitable for pigmenting high-molecular organic material.
    Type: Grant
    Filed: February 17, 1987
    Date of Patent: October 4, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Georg Cseh, Paul Lienhard
  • 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: 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: 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: 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: 4625017
    Abstract: Metallizable azo dyes of the formula I ##STR1## wherein A is the radical of a diazo component of the benzene or naphthalene series, which diazo component contains in the o-position with respect to the azo group a metallizable hydroxyl group,R is methyl or chloromethyl, or phenyl which can be substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen,R.sub.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl,R.sub.2 is hydrogen or methyl,n is 0 or 1, andm is 0, 1, 2 or 3.In the form of their heavy-metal complexes, the dyes are suitable in particular for dyeing leather. These dyes are deeply colored, cover well, have good substantivity and build-up while simultaneously having good fastness properties.
    Type: Grant
    Filed: November 12, 1982
    Date of Patent: November 25, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Alois Puntener
  • Patent number: 4617382
    Abstract: The present invention relates to novel chromium complex dyes of the formula ##STR1## wherein Z is hydrogen, chloro, bromo, nitro, lower alkyl or acylamino;L is H.sub.
    Type: Grant
    Filed: April 13, 1983
    Date of Patent: October 14, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Gerhard Back, Fabio Beffa, Arthur Buhler
  • Patent number: 4599402
    Abstract: The novel compounds of the general formula I ##STR1## where A is a radical of a coupling or diazo component which, if necessary after conversion, is capable of complex formation, Ar is an unsubstituted or substituted aromatic or heterocyclic radical, D is a radical of a diazo component and Me is a Co.sup.2+, Cu.sup.2+, Zn.sup.2+, Mn.sup.2+ or Ni.sup.2+ ion, and the ring B can be further substituted, are very useful for dyeing cellulose fibers, polyesters and blends of cellulose fibers and polyesters.The present dyes are lightfast and fast to washing and to solvents.
    Type: Grant
    Filed: October 12, 1984
    Date of Patent: July 8, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Johannes Dehnert, Werner Junemann
  • Patent number: 4563193
    Abstract: The novel asymmetric 1:2 chrome complex dyes of the formula I given in claim 1 are suitable in particular for dyeing wool or polyamide and especially leather.
    Type: Grant
    Filed: November 7, 1983
    Date of Patent: January 7, 1986
    Assignee: Ciba Geigy Corporation
    Inventor: Fabio Beffa
  • Patent number: 4560744
    Abstract: Compounds which in the form of the free acids correspond to the formula ##STR1## where A is a radical of a diazo component or of an amine,B is a radical of a coupling component or of an aldehyde,R.sup.1 is chlorine or bromine,R.sup.2 is methoxy or ethoxy,X is .dbd.N-- or .dbd.CH--,Y is --O-- or --COO-- andZ is --O-- or --NH--,are dyes which are very suitable for dyeing nylons and natural polyamides.
    Type: Grant
    Filed: March 6, 1981
    Date of Patent: December 24, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Baumann, Klaus Grychtol
  • 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: 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
  • Patent number: 4507124
    Abstract: The dyes of the formula I ##STR1## in which Me is cobalt or chromium, A and A' independently of each other are each the radical of an amine of the benzene series which carries the hydroxyl group in the o-position relative to the azomethine group, Ar.sub.1 and Ar.sub.3 independently of each other are each a substituted or unsubstituted phenylene or naphthylene radical, Ar.sub.2 and Ar.sub.4 independently of each other are each a substituted or unsubstituted benzene or naphthalene radical, m and n independently of each other are each 0 or 1, p is an integer from 3 to 6 and Ka.sym. is a cation, are suitable for dyeing polyamides, particularly wool and leather.
    Type: Grant
    Filed: June 20, 1983
    Date of Patent: March 26, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Alois Puntener, Fabio Beffa
  • 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
  • Patent number: 4497734
    Abstract: Asymmetrical 1:2 chromium complex dyestuffs which, in the form of the free acid, correspond to the formula ##STR1## wherein X represents CO or a direct bond andm represents 0 or 1 andthe rings a, b and c and, if present, fused-on benzene rings can carry further substituents customary in the chemistry of metal complex dyestuffs,are used for dyeing materials containing amide groups, in particular leather, and produce dyeings having a green hue and good general fastness properties.
    Type: Grant
    Filed: August 3, 1982
    Date of Patent: February 5, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventor: Winfried Mennicke
  • Patent number: 4493798
    Abstract: Metallizable disazo dyes of the formula (1) ##STR1## in which A and A' independently of one another are each the radical of a diazo component of the benzene or naphthalene series, at least one of the groups A or A' carrying a metallizable hydroxyl or carboxyl group in the o-position relative to the azo group, and X is substituted or unsubstituted phenylene, naphthylene or C.sub.2 -C.sub.4 -alkylene and R is C.sub.1 -C.sub.4 -alkyl, COO-Q or CONQQ.sub.1, in which Q and Q.sub.1 are each hydrogen or C.sub.1 -C.sub.4 -alkyl.In the form of their cobalt or chromium complexes, the dyes are suitable for dyeing natural or synthetic polyamide materials, and especially wool or leather.
    Type: Grant
    Filed: September 8, 1981
    Date of Patent: January 15, 1985
    Assignee: Ciba Geigy Corporation
    Inventor: Fabio Beffa
  • Patent number: 4489002
    Abstract: Compounds of the general formula I ##STR1## where E is --CH.dbd. or --N.dbd., K is the radical of an amine or of a coupling component of the benzene, naphthalene, pyrazole, pyridine, pyrimidine, quinoline or isoquinoline series, or the radical of a 1,3-dicarbonyl compound which can be coupled, X is --O-- or --COO--, Y is --O--, --COO-- or --NH--, Z.sup.1 and Z.sup.2 independently of one another are unsubstituted or substituted alkyl or cycloalkyl, and one of them may furthermore be unsubstituted or substituted aryl, or Z.sup.1 and Z.sup.2 together with the nitrogen atom are a heterocyclic radical, and Z is unsubstituted or substituted C.sub.2 - or C.sub.3 -alkylene, from 1 to 4 sulfonic acid groups can be present and the rings A and B can be further substituted or can carry a fused benzene ring.The compounds of the present invention are suitable for dyeing or printing natural or synthetic N-containing materials, i.e., wool, leather or polyamide or polyurethane fibers, as wells as for coloring inks.
    Type: Grant
    Filed: June 4, 1982
    Date of Patent: December 18, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Baumann, Klaus Grychtol
  • Patent number: 4486196
    Abstract: Chrome-complex dyes of the formula (I) ##STR1## wherein the phenyl groups A and B independently of one another are each unsubstituted or are mono- or disubstituted by chlorine, methyl, ethyl, methoxy or ethoxy, and wherein Me.sup..sym. is a cation.The dyes are suitable for dyeing nitrogen-containing materials, particularly for dyeing wool in orange shades.
    Type: Grant
    Filed: January 16, 1984
    Date of Patent: December 4, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Alois Puntener