Sulfonated Azo Patents (Class 8/681)
  • Patent number: 5399183
    Abstract: Process for the trichromatic dyeing or printing of natural or synthetic polyamide fibre materials, which comprises using at least one blue-dyeing anthraquinone dye of the formula ##STR1## in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4, independently of one another, are hydrogen or C.sub.1 -C.sub.6 alkyl, the sum of the carbon atoms of the radicals R.sub.1, R.sub.2, R.sub.3 and R.sub.4 being 4, 5 or 6 and the sulfo group in the anthraquinone dye of the formula (1) being attached in the position designated as 6 or 7, together with at least one red-dyeing dye of the formula (2) and at least one of the yellow- or orange-dyeing dyes of the formulae (3), (4) and (5), the dyes of the formulae (2), (3), (4) and (5) being as defined in claim 1.The process according to the invention is suitable for dyeing natural or synthetic polyamide materials from an aqueous liquor or for printing with printing pastes.
    Type: Grant
    Filed: November 24, 1993
    Date of Patent: March 21, 1995
    Assignee: Ciba-Geigy Corporation
    Inventor: Jean-Marie Adam
  • Patent number: 5393306
    Abstract: Dye mixtures which comprise a reactive dye of the formula ##STR1## together with at least one reactive dye of the formulae ##STR2## in which D, D', R.sub.1, R.sub.2, R.sub.3, R.sub.3 ' and B are as defined in claim 1, are particularly suitable for dyeing or printing cellulosic fibre materials or naturally occurring or synthetic polyamide fibre materials with a high tinctoffal yield, and produce dyeings and prints having good fastness properties.
    Type: Grant
    Filed: July 19, 1993
    Date of Patent: February 28, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Claudia Carisch
  • Patent number: 5393307
    Abstract: A reactive dyestuff mixture showing improved compatibility contains at least one vinylsulphonyltriazine dyestuff 1, at least one monofluorotriazine dyestuff 2 or fluorochloropyrimidine dyestuff 3 together with, if desired, additional dyestuffs.
    Type: Grant
    Filed: August 3, 1993
    Date of Patent: February 28, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Max Schwarz, Joachim Grutze, Dietrich Hildebrand, Joachim Wolff, Frank-Michael Stohr
  • Patent number: 5360472
    Abstract: Disclosed are dye compositions of the formula ##STR1## wherein Cp and Cp' are each coupler compounds of the formula ##STR2## wherein the --COOH group and the --OH group can be in any position on either ring, provided that in the naphthalene ring system there is present least one hydrogen activated through resonance by the --OH group for an electrophilic aromatic substitution coupling reaction, n represents the number of substituents on the rings and is a number of from 0 to 8, and R represents the substituent groups on the ring, wherein each R is independently selected from the group consisting of hydroxyl groups, alkyl groups, substituted alkyl groups, aryl groups, substituted aryl groups, aryl-alkyl groups, substituted aryl-alkyl groups, halogen atoms, and nitro groups. Also disclosed are aqueous ink compositions containing the dyes, processes for making the dyes, processes for making the inks containing the dyes, and printing processes employing the inks.
    Type: Grant
    Filed: July 26, 1993
    Date of Patent: November 1, 1994
    Assignee: Xerox Corporation
    Inventors: Edward J. Radigan, Jr., Louis V. Isganitis, Warren E. Solodar, Kurt B. Gundlach
  • Patent number: 5356445
    Abstract: The invention relates to a process for dyeing natural or synthetic polyamide fiber material from an aqueous liquor, in the presence of a levelling assistant and in the presence or absence of an alkali metal fluorosilicate or ammonium fluorosilicate, which process comprises the use of a mixture of the dyes of formulae (1), (2) and (3) or a mixture of the dyes of formulae (4) and (5), or a mixture which contains the dye of formula (6) together with at least one dye of formulae (7), (8) and (9), which dyes of fomaulae (1) to (9) are as defined in claim 1.The inventive process is suitable for dyeing natural or synthetic polyamide fiber material to give dyeings of fiber and surface levelness having good fastness properties.
    Type: Grant
    Filed: September 24, 1993
    Date of Patent: October 18, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Christian De Meulemeester, Patrick Runser
  • Patent number: 5350426
    Abstract: Nylon fibers of cationic-dyeable nylon are dyed with an acid or premetalized acid dye and heatset to impart stain and bleach resistance. Stain and bleach resistant nylon carpets prepared from these fibers are also described.
    Type: Grant
    Filed: August 11, 1993
    Date of Patent: September 27, 1994
    Assignee: Burlington Industries, Inc.
    Inventor: William G. Jenkins
  • Patent number: 5342417
    Abstract: A method for reducing the cold water bleed propensity of acid and premetallized acid dyed cationic dyeable nylon fibers which comprises treating such fibers with sulfonated anionic polymers, useful as nylon fixing agents, and cationic amine based polymers, useful as cotton fixing agents.
    Type: Grant
    Filed: December 16, 1992
    Date of Patent: August 30, 1994
    Inventors: Joseph A. Pacifici, Daniel G. Sims
  • Patent number: 5330539
    Abstract: A method for the exhaust dyeing of materials having hydroxy groups and materials containing carbonamide groups using a low salt content dye bath in conjunction with fiber reactive dyes exemplified by a dye of the following formula: ##STR1##
    Type: Grant
    Filed: December 18, 1991
    Date of Patent: July 19, 1994
    Assignee: Hoechst Celanese Corporation
    Inventors: Thomas S. Phillips, Kevin D. Costa, Werner Russ, Thomas V. Chambers
  • Patent number: 5324330
    Abstract: Dye mixtures comprising at least one dye of formula ##STR1## and at least one dye of formula ##STR2## wherein the substituents are as defined in claim 1, have good allround fastness properties and are suitable for dyeing cellulosic fibre materials.
    Type: Grant
    Filed: December 10, 1992
    Date of Patent: June 28, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Rudolf Schaulin, Urs Lauk
  • Patent number: 5320648
    Abstract: The invention relates to a process for dyeing or printing hydroxyl group containing fibre materials, which comprises using at least one yellow or orange dyeing dye of formula ##STR1## wherein the substituents are as defined in claim 1, together with at least one blue dyeing dye and/or at least one red dyeing dye. Level dyeings and prints with good allround fastness properties are obtained by the process of the invention.
    Type: Grant
    Filed: December 16, 1992
    Date of Patent: June 14, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: David H. McMullan, Rudolf Schaulin, Urs Lauk
  • Patent number: 5320647
    Abstract: Fluent dye preparations useful for dyeing leather or wool containa) at least 15% of the weight of the dye preparation of one or more polyazo dyes in salt form which have one or more hydroxysulfonyl and/or carboxyl groups and may be present in the form of a 1:1 or 1:2 metal complex,b) from 2 to 15% of the weight of the dye preparation of a surfactant, andc) water.
    Type: Grant
    Filed: August 14, 1992
    Date of Patent: June 14, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Georg Henning, Georg Zeidler, Ortwin Schaffer
  • Patent number: 5319075
    Abstract: Mixtures of iron complexes of metallizable disazo compounds, at least one compound being of the formula ##STR1## and at least one compound being of the formula ##STR2## wherein the substituents have the meaning given in the specification, are useful for dyeing substrates dyeable with anionic dyes, e.g., leather.
    Type: Grant
    Filed: February 22, 1993
    Date of Patent: June 7, 1994
    Assignee: Sandoz Ltd.
    Inventors: Jordi Berenguer Barra, Herbert Holliger, Jose Rocas Sorolla
  • Patent number: 5290347
    Abstract: The present invention provides a novel salt-forming type dye represented by the formula: ##STR1## wherein D is a residue of a monoazo or disazo dye, m is an integer of 1 to 3, n is an integer of 1 to 4, and M.sup.+ is a cation selected from the group consisting of cations represented by the formulas: ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and represent hydrogen, an alkyl group, an alkoxyalkyl group, a cyclohexyl group, an aralkyl group or a hydroxyalkyl group, and at least one of R.sup.1 to R.sup.4 is a branched or non-branched alkyl, alkoxyalkyl, cycloalkyl, aralkyl or polyoxyalkylene group having not less than 4 carbon atoms, ##STR3## wherein R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are the same or different and represent hydrogen, an alkyl group, or a substituted or non-substituted phenyl group, and at least one of R.sup.5 to R.sup.8 is a substituted or non-substituted phenyl group, and ##STR4## wherein R.sup.9 and R.sup.
    Type: Grant
    Filed: April 9, 1992
    Date of Patent: March 1, 1994
    Assignee: Orient Chemical Industries, Ltd.
    Inventors: Takashi Ono, Tatsuya Yagyu, Katsumi Fukuda
  • Patent number: 5288294
    Abstract: The dyes of formula ##STR1## wherein X, Y and M are as defined in claim 1, are suitable for dyeing paper with good lightfastness.
    Type: Grant
    Filed: September 21, 1992
    Date of Patent: February 22, 1994
    Assignee: Ciba-Geigy Corporation
    Inventor: Adolf Kaser
  • Patent number: 5234467
    Abstract: The invention relates to a dye mixture comprising at least one dye of the formula ##STR1## in which R.sub.1 and R.sub.2, independently of one another, are hydrogen or substituted or unsubstituted C.sub.1 -C.sub.8 alkyl or phenyl, R.sub.3 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.8 alkyl, C.sub.5 -C.sub.7 cycloalkyl or phenyl, R.sub.4 is hydrogen or a radical of the formula ##STR2## R.sub.5 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.8 alkyl or phenyl, and benzene rings I and II may be further substituted, together with at least one dye of the formulae (2) to (6) given in the description.The dye mixtures are suitable for the dyeing or printing of natural and synthetic polyamide fibre materials, in particular in combination with other dyes.
    Type: Grant
    Filed: July 14, 1992
    Date of Patent: August 10, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Jurgen Schaetzer
  • Patent number: 5211719
    Abstract: Concentrated aqueous solutions are described comprising specific anionic disazo dyes and polyglycol amines, which are highly suitable as commercial forms.
    Type: Grant
    Filed: September 27, 1991
    Date of Patent: May 18, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Adolf Kaser
  • Patent number: 5176717
    Abstract: The use of compounds of the formula ##STR1## in which the symbols are as defined in claim 1, for dyeing leather is described.
    Type: Grant
    Filed: July 19, 1991
    Date of Patent: January 5, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Rudolf Schaulin, Peter Moser, Alois Puntener
  • Patent number: 5171328
    Abstract: Wood stains contain in addition to a colorant and a solvent at least one stabilizer against the action of light, oxygen and heat on the wood treated with the wood stain, said stabilizer containing at least one structural element of the formula I ##STR1## where X is oxygen or nitrogen.
    Type: Grant
    Filed: October 4, 1991
    Date of Patent: December 15, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Hubert Trauth, Christos Vamvakaris
  • Patent number: 5152801
    Abstract: There is disclosed a process for dyeing leather by the exhaust process, which comprises treating leather with an aqueous liquor which contains a formulation comprising a black anionic dye and a sulfonated carbon black. The leather dyeings obtained by this process have good allround fastness properties.
    Type: Grant
    Filed: December 5, 1990
    Date of Patent: October 6, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans Altermatt, Alois Puntener, Peter Moser, Ernst Tempel
  • Patent number: 5123930
    Abstract: 1:2 metal complexes of the formula ##STR1## wherein each of R.sub.1 and R.sub.3 is independently hydrogen or nitro, with the proviso that when a ring has two nitro groups, they are meta to each other,each of R.sub.2 and R.sub.4 is independently hydrogen, chloro or --SO.sub.3 M,each of R.sub.5 and R.sub.6 is independently hydrogen, --COR.sub.7, --CONHR.sub.8 or --SO.sub.2 R.sub.9,whereinR.sub.7 is C.sub.1-6 alkyl, C.sub.1-6 alkoxy, phenyl(C.sub.1-4 -alkyl) or phenyl (C.sub.1-4 alkyl) the phenyl group of which is substituted by 1 or 2 substituents selected from halo, C.sub.1-4 -alkyl, C.sub.1-4 alkoxy, nitro, amino, --COOM, --SO.sub.3 M and acetamido,R.sub.8 is hydrogen; C.sub.1-6 alkyl; phenyl; phenyl substituted by 1 or 2 substituents selected from halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, nitro, amino, --COOM, --SO.sub.3 M and acetamido; naphthyl or naphthyl monosubstituted by chloro, amino, phenylamino, acetamido, benzamido or --SO.sub.3 M, andR.sub.9 is C.sub.
    Type: Grant
    Filed: August 21, 1990
    Date of Patent: June 23, 1992
    Assignee: Sandoz Ltd.
    Inventor: Peter Bitterli
  • Patent number: 5102459
    Abstract: The invention relates to a method using water-soluble dyestuffs for coloring recording fluids, particularly in the ink jet process, wherein the dyestuffs in the form of the free acid have the general formula A--(SO.sub.2 -X).sub.p.The dyestuffs (I) can be prepared analogously to methods for preparing known vinylsulfone or .beta.-sulfatoethylsulfone dyestuffs which are further reacted with nucleophiles R.sup.1 OH, HNR.sup.1 R.sup.2, HSR.sup.1 etc. Some of the reaction products are novel dyestuffs.
    Type: Grant
    Filed: May 28, 1991
    Date of Patent: April 7, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Josef Ritter, Alexander Sieber
  • Patent number: 5092905
    Abstract: Dye mixtures comprising(i) as a yellow component, at least one compound of the formula ##STR1## or a salt thereof, wherein R.sub.1 is hydrogen, C.sub.1-4 alkoxy, C.sub.1-4 alkyl or C.sub.1-4 alkyl monosubstituted by halo,R.sub.2 is C.sub.1-4 alkyl or --COR.sub.6,wherein R.sub.6 is C.sub.1-6 alkyl, C.sub.1-6 alkoxy or --NR.sub.7 R.sub.8,wherein each of R.sub.7 and R.sub.8 is independently hydrogen, C.sub.1-6 -alkyl or C.sub.2-6 alkyl mono-substituted by hydroxy,R.sub.4 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or --NR.sub.3 R.sub.9,R.sub.5 is c.sub.1-4 alkyl or C.sub.2-6 alkyl monosubstituted by hydroxy,R.sub.10 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or --NR.sub.3 R.sub.9, andR.sub.11 is hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, whereineach R.sub.3 is independently hydrogen or C.sub.1-4 alkyl, andeach R.sub.9 is independently (C.sub.1-6 alkyl)carbonyl or (C.sub.
    Type: Grant
    Filed: October 4, 1990
    Date of Patent: March 3, 1992
    Assignee: Sandoz Ltd.
    Inventor: Jacky Dore
  • Patent number: 5085667
    Abstract: Stain-resistant nylon, especially cationic-dyeable carpet nylon, is prepared by dyeing cationic-dyeable nylon fibers with acid or premetalized dye. Lightfastness and depth of shade of an apparent value equal to acid dyeable nylons is obtained with superior stain resistance equal to commercially available solution dyed nylon carpeting.
    Type: Grant
    Filed: July 12, 1990
    Date of Patent: February 4, 1992
    Assignee: Burlington Industries, Inc.
    Inventor: William G. Jenkins
  • Patent number: 5071442
    Abstract: A process for dyeing or printing cellulosic textile fibre materials by the trichromatic technique, which process comprises dyeing or printing said materials from an aqueous liquor with at least one red or reddish brown dyeing dye of formula ##STR1## and at least one yellow or orange dyeing dye of formula ##STR2## and at least one blue dyeing dye of formula ##STR3## wherein A.sub.1, A.sub.2, (B.sub.2).sub.1-3, R.sub.1, R.sub.2, R.sub.3, (R.sub.4).sub.1-2, (X).sub.1-2, (T.sub.1).sub.1-2, (T.sub.2).sub.1-2, (Y).sub.1-3 and Z in formulae (1) to (7) are as defined in claim 1.The process of this invention is suitable for dyeing or printing cellulosic fibre materials.
    Type: Grant
    Filed: January 4, 1991
    Date of Patent: December 10, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Jean P. Luttringer, Athanassios Tzikas, Pierre Galafassi
  • Patent number: 5049189
    Abstract: A liquid dyestuff, useful as a major component of a ballpoint ink is prepared. A dye base, having both a sulfonic acid group and an azo group bonded to the same aromatic ring system, is provided in the aqueous phase of a two-phase system in which the organic phase is about 30 percent or more benzyl alcohol. In this two-phase system, the dye base is complexed with a diaryl quanidine, and the resulting dye concentrates in the organic solvent phase.
    Type: Grant
    Filed: February 2, 1990
    Date of Patent: September 17, 1991
    Assignee: Morton International, Inc.
    Inventors: Michael R. Friswell, Michael P. Hinton, Alejandro Zimin
  • Patent number: 5045084
    Abstract: A process for the trichromatic dyeing or printing of natural and synthetic polyamide fibre materials, which comprises using at least one red dye of the formula ##STR1## in which D,R.sub.1,R.sub.2,R.sub.3,R.sub.4 and n are as defined in claim 1, together with at least one yellow or orange dye of the formula ##STR2## in which B.sub.1,B.sub.2,E.sub.1 and X are as defined in claim 1, or ##STR3## in which Z.sub.1,Z.sub.2 and Z.sub.3 are as defined in claim 1, or mixtures of dyes of the formulae (2) and (3), or a yellow dye of the formula ##STR4## in which W.sub.1,W.sub.2,W.sub.3 and W.sub.4 are as defined in claim 1, or mixtures of dyes of the formulae (2),(3) and (4) and at least one blue dye of the formula ##STR5## in which one Y and Z.sub.4 are as defined in claim 1 are used. The process according to the invention is suitable for dying natural or synthetic polyamide materials from aqueous liquor or for printing with printing pastes; and in particular for dyeing from short liquors.
    Type: Grant
    Filed: October 18, 1990
    Date of Patent: September 3, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Harald Walter
  • Patent number: 5043257
    Abstract: Azo dyes of the formula ##STR1## where X is alkyl or alkoxy each of 1 to 4 carbon atoms or halogen, X' is hydrogen, alkyl or alkoxy each of 1 to 4 carbon atoms or halogen, Y and Y' are independently of each other hydrogen or halogen, Z is hydrogen, alkyl or alkoxy or alkylthio each of 1 to 4 carbon atoms, or halogen, M is a 1-, 2- or 3-valent metal cation, ammonium or an organic ammonium compound, m is 1, 2 or 3 and n is 2 to 10, are suitable for use as image dyes in photographic silver dye bleach materials.The dyes of the invention can also be used to dye textile materials.
    Type: Grant
    Filed: December 8, 1989
    Date of Patent: August 27, 1991
    Assignee: Ilford Limited
    Inventors: Kurt Baettig, Gerald C. Jan
  • Patent number: 5034017
    Abstract: Dyestuffs of the formula ##STR1## in which the substituents have the meanings given in the description are highly suitable for the coloration of paper. They produce light and wetfast blue coloring.
    Type: Grant
    Filed: March 21, 1990
    Date of Patent: July 23, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Kunde, Peter Wild
  • Patent number: 5032142
    Abstract: Trichromatic dye mixtures containing(i) as the orange componentat least one dye of the formula ##STR1## or a salt thereof, or, as the yellow component,at least one dye of the formula ##STR2## or a salt thereof, whereinR.sub.1 is hydrogen or C.sub.1-4 alkyl,R.sub.2 is hydrogen, C.sub.1-4 alkyl or substituted C.sub.1-4 alkyl,each of R.sub.3 and R.sub.4 is independently hydrogen, C.sub.1-6 alkyl or substituted C.sub.1-6 alkyl,R.sub.10 is hydrogen or C.sub.2-3 hydroxyalkyl, andR.sub.11 is C.sub.2-3 hydroxyalkyl or 2-(2'-hydroxyethoxy)ethyl, with the proviso that when R.sub.11 is 2-(2'-hydroxyethoxy)ethyl, R.sub.10 must be hydrogen,(ii) as the red component,at least one dye of the formula ##STR3## or a salt thereof, wherein each of D and D' is independently ##STR4## wherein m is 1 or 2, each R.sub.5 is independently hydrogen or C.sub.1-4 alkyl,each R.sub.6 is independently hydrogen, C.sub.1-4 alkyl or C.sub.2-4 hydroxyalkyl, andx is linear or branched C.sub.2-6 alkylene, linear or branched C.sub.
    Type: Grant
    Filed: December 21, 1989
    Date of Patent: July 16, 1991
    Assignee: Sandoz Ltd.
    Inventors: Walter B. Egger, Ernst Schnider
  • Patent number: 5007941
    Abstract: There is disclosed a process for dyeing leather by the exhaust process, which comprises treating leather with an aqueous liquor which contains a formulation comprising an anionic dye and a pigment. The leather dyeings obtained by this process have good allround fastness properties.
    Type: Grant
    Filed: December 21, 1989
    Date of Patent: April 16, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Bruno Martinelli, Markus Ghezzi, Gunter Streicher
  • Patent number: 5006128
    Abstract: Compounds of the formula ##STR1## and salts thereof, whereinR.sub.1 is hydrogen or methyl,R.sub.2 is hydrogen, methyl or acetamido,R.sub.3 is hydrogen, methyl or methoxy,R.sub.4 is hydrogen, C.sub.1-4 alkyl or hydroxy(C.sub.2-4 alkyl),R.sub.5 is hydroxy(C.sub.2-4 alkyl) or hydroxy(C.sub.2-4 alkoxy)C.sub.2-4 alkyl, or--NR.sub.4 R.sub.5 is a 5- or 6-membered ring containing 1 to 3 hetero atoms which ring is unsubstituted or substituted by 1 to 3 substituents selected from C.sub.1-4 alkyl and C.sub.2-4 alkyl monosubstituted by hydroxy or amino, andthe two naphthyl-2 groups are identically substituted, with the proviso that when R.sub.3 is methoxy, R.sub.1 and R.sub.2 are different, solid and aqueous liquid dye compositions and printing inks comprising such compounds and salts and the use of such compounds and salts for dyeing and printing substrates, especially hydroxy group- and nitrogen-containing organic substrates.
    Type: Grant
    Filed: August 25, 1989
    Date of Patent: April 9, 1991
    Assignee: Sandoz Ltd.
    Inventor: Reinhard Pedrazzi
  • Patent number: 4954133
    Abstract: Compounds of the formula ##STR1## wherein each A, independently, is a ##STR2## wherein R.sub.1 is hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,R.sub.2 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, --NHCONH.sub.2 or --NHCOC.sub.1-4 alkyl,R.sub.3 is hydrogen or methoxy, andm is 0, 1 or 2,each B, independently, is a radical of a diazo or coupling component, and a and each b, independently, are 0 or 1,and metal complexes thereof, which compounds or complexes are in free acid or salt form, and mixtures thereof with a compound of the formula ##STR3## or a metal complex thereof, wherein A and b are as defined above and D is a radical of a diazo or coupling component of the benzene or 1-naphthalene series are useful for dyeing and printing hydroxy group- or nitrogen-containing organic substrates, especially cellulose fibre-containing textiles (e.g., cotton), paper and leather.
    Type: Grant
    Filed: February 12, 1986
    Date of Patent: September 4, 1990
    Assignee: Sandoz Ltd.
    Inventor: Max Oppliger
  • Patent number: 4935033
    Abstract: Natural polyamide fibres, in particular wool, are dyed by means of reactive dyes using the exhaust method in the presence of a dyeing assistant consisting of a combination of (a) quaternized ammonium compounds of polyglycol compounds and (b) of acidic esters or salts thereof derived from at least dibasic oxyacids and from polyglycol compounds, both the quaternary ammonium compounds and the acidic esters being derived from an aliphatic amine having 12 to 24 carbon atoms in the aliphatic moiety. The process comprises carrying out the dyeing in the additional presence of (c) a fatty alcohol/polyalkylene glycol ether of the formulaR-O-(alkylene-O.sub.m H (1)in which R is an aliphatic radical having at least 8 carbon atoms, "alkylene" is an ethylene radical or propylene radical and m is 3 to 25.
    Type: Grant
    Filed: September 21, 1988
    Date of Patent: June 19, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Walter Mosimann, Dieter Mausezahl
  • Patent number: 4923481
    Abstract: Aqueous dispersion of a sulfonated metallizable dye containing(a) based on the total weight at least 10% of the sulfonated metallizable dye and(b) a sulfonated condensation product obtained by reacting an aromatic compound having at least two replaceable ring-positioned hydrogen atoms in any desired order with a compound of the formula ##STR1## in which X is a direct bond or oxygen, Hal is chlorine or bromine and n is 1 to 4, and sulfonation.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: May 8, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Roberto Galli, Ernst Tempel
  • 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: 4894065
    Abstract: The invention refers to a mixture of anionic dyestuffs having a skitteriness value at pH5 of 3-4 and a combinability value at pH5 of 4-5 and to a process for dyeing a fibre material comprising wool with such a mixture of dyestuffs. These mixtures of anionic dyestuffs give surface and fibre level dyeings.
    Type: Grant
    Filed: March 3, 1988
    Date of Patent: January 16, 1990
    Assignee: Sandoz Ltd.
    Inventors: Oskar Annen, Wolfgang Beck, Josef Frauenknecht
  • Patent number: 4876333
    Abstract: A crystalline modification, designated ".beta.", of the dye of the structure ##STR1## The .beta.-crystalline modification of the dye is easier to isolate from water and gives filter cakes of higher solids and color content. The .beta.-form is also more suitable for making liquid formulations of the dye; the liquid formulations of the crystalline modification have lower viscosity and better dispersion stability than liquid formulations of non-modified form. The .beta.-modification of the dye is obtained by heating an aqueous slurry of the dye at about 90.degree.-95.degree. C. and pH of 8.5 to 9.5 until the modification is complete. The crystalline modification of the dye gives Debye-Scherrer X-ray diffraction patterns substantially different from the non-modified form.
    Type: Grant
    Filed: October 15, 1985
    Date of Patent: October 24, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Alfred Hoehener, Roy E. Smith
  • Patent number: 4874391
    Abstract: A process for the photochemical stabilization of polyamide fiber material or mixtures thereof with other fiber materials which comprises treating the fiber material with a mixture of (A) a water-soluble copper complex dye or a mixture of copper complex compounds, at least one component being a water-soluble copper complex dye, (B) a light stabilizer and if desired (C) an antioxidant, an agent for carrying out the process and the fiber material treated therewith are described.
    Type: Grant
    Filed: July 20, 1987
    Date of Patent: October 17, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Gerhard Reinert
  • Patent number: 4872881
    Abstract: A dye mixture and a method of dyeing cellulosic fibers by use of the dye mixture, the dye mixture being capable of dyeing the cellulosic fibers favorably even in the presence of a small amount of an inorganic salt at dyeing, and being composed of a blend of a red water-soluble reactive dye to be represented by the following general formula (I) in the form of free acid, and a specific yellow and/or blue water-soluble reactive dye: ##STR1## (where: each of R.sup.1 and R.sup.2 denotes a hydrogen atom or a lower alkyl group which may contain therein a substituent; R.sup.3 represents a hydrogen atom, a lower alkyl group or a halogen atom and X designates --CH.dbd.CH.sub.2 or --C.sub.2 H.sub.4 OSO.sub.3 H).
    Type: Grant
    Filed: October 31, 1988
    Date of Patent: October 10, 1989
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Takashi Fujita, Toshio Hihara, Yoshio Kogure, Riyouichi Sekioka, Noboru Nakamura
  • Patent number: 4861344
    Abstract: Water-soluble azo compounds having useful fiber-reactive dye properties conforming to the general formula ##STR1## in which: A is phenylene which may be substituted or unsubstituted, or is a radical of the formula ##STR2## in which W is a direct bond or a radical of the formula --CH.dbd.CH-- or --NH--CO--NH-- and R* denotes hydrogen, nitro, sulfo, carboxy, methyl, ethyl, methoxy or ethoxy;n is the number zero or 1;B is a radical of the formula ##STR3## where R is equal to carboxy or carbamoyl; M is hydrogen or an alkali metal; andK is one of five radicals described in the specification, each of which contains a fiber-reactive group.These azo compounds produce fast dyeings on carboxamido- and/or hydroxy-containing materials, in particular cellulose fibers. On cellulose, fast dyeings are also obtained in a weakly acid to neutral medium, for example together with disperse dyes for dyeing a polyester fiber portion.
    Type: Grant
    Filed: October 30, 1987
    Date of Patent: August 29, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ludwig Schlafer, Hartmut Springer, Reinhard Hahnle
  • Patent number: 4840642
    Abstract: Compounds of the formula ##STR1## and salts thereof, useful for dyeing and printing hydroxy group - or nitrogen-containing organic substrates, for example, leather and fibrous materials containing or consisting of natural or synthetic polyamides or natural or regenerated cellulose; preferably textile material containing or consisting of cotton which is preferably dyed using the exhaust dyeing method.
    Type: Grant
    Filed: September 4, 1987
    Date of Patent: June 20, 1989
    Assignee: Sandoz Ltd.
    Inventors: Gunther Auerbach, Helmut A. Moser
  • Patent number: 4838895
    Abstract: Concentrated aqueous dye formulations of anionic dyes are prepared from the corresponding crude dye solutions or suspensions, in which the anionic dyes are present as potassium, sodium/potassium or ammonium/potassium mixed salts, by desalinating and concentrating the solutions or suspensions by means of a membrane separation process. Sodium salts of mineral acids or lower organic carboxylic acids are added before or during this process in order to improve the solubility of the dyes and thus the stability of the dye formulations.
    Type: Grant
    Filed: April 8, 1988
    Date of Patent: June 13, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Roberto Galli, Petr Kvita
  • Patent number: 4836827
    Abstract: The compounds of the formula (1) given in claim 1 are suitable for use as dyes for dyeing a wide range of textile and non-textile materials and in particular for dyeing leather and pelts.
    Type: Grant
    Filed: January 29, 1988
    Date of Patent: June 6, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Alois Puntener
  • Patent number: 4828572
    Abstract: The invention relates to a process for dyeing or printing textile fibre materials in stable shades with reactive dyes which produce grey or black dyeings or prints, which process comprises dyeing or printing textile fibre materials with a mixture of heavy metal-containing, water-soluble reactive dyes which produce grey or black dyeings or prints, each component of which mixture, under identical dyeing, printing and fixation conditions, produces dyeings or prints with a tinge different from the tinge of the dyeings or prints produced by the other component, and carrying out subsequent fixation.
    Type: Grant
    Filed: October 13, 1987
    Date of Patent: May 9, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Wolfgang Sutterlin, Rainer Begrich
  • Patent number: 4818247
    Abstract: Reactive dyes of the formula ##STR1## in which D is the radical of a diazo component of the benzene, naphthalene, azobenzene, naphthylazobenzene, azonaphthalene or phenylazonaphthalene series, K is the radical of a coupling component of the benzene or naphthalene series or of the heterocyclic series, except a pyrazolone radical, R.sub.1 and R.sub.2, independently of each other, are each hydrogen or an unsubstituted or substituted C.sub.1-4 -alkyl radical, and X.sub.1 and X.sub.2, independently of each other, are each unsubstituted or substituted aminofluoro-s-triazinyl, are particularly suitable for dyeing and printing cellulose-containing fibre materials and produce, in high dyeing yield, dyeings and prints having good fastness properties.
    Type: Grant
    Filed: May 21, 1987
    Date of Patent: April 4, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Adolf Kaser
  • Patent number: 4816034
    Abstract: A water soluble direct black polyazo dyestuffs mixture comprising trisazo dyestuffs, polyazo dyestuffs and disazo dyestuff.
    Type: Grant
    Filed: August 12, 1986
    Date of Patent: March 28, 1989
    Assignee: The Atul Products Limited
    Inventors: Girish I. Bhatt, Subrao S. Kulkarni, Chandrashekhar B. Upasani, Mukundbhai Bhatt
  • Patent number: 4808193
    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: May 26, 1988
    Date of Patent: February 28, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ludwig Schlafer, Hartmut Springer, Michael Kunze
  • Patent number: 4802887
    Abstract: A composition comprising:(a) 30 to 90% by weight of one or more water soluble anionic dyestuffs in metal complex form,(b) 0.5 to 20% by weight of one or more compounds of formula I ##STR1## in which R.sub.1 is C.sub.12-22 alkyl or C.sub.12-22 alkenyl; R.sub.2 is hydrogen or --SO.sub.3 M;m is 2, 3 or 4;n is 2, 3 or 4;p+p' is 10 to 30 inclusive, each of p and p' being at least 1; and M is a cation; and(c) 5 to 40% by weight of a dispersing agent.These compositions are suitable for dyeing of textile and leather substrates.
    Type: Grant
    Filed: March 10, 1987
    Date of Patent: February 7, 1989
    Assignee: Sandoz Ltd.
    Inventor: Kamal Ateya
  • Patent number: 4780104
    Abstract: An aqueous liquid dye composition comprising 5 to 50% by weight of a reactive dye represented by the following formula, ##STR1## wherein D denotes a sulfo group-containing organic dye residue, R.sub.1 and R.sub.2 independently of one another denote a hydrogen atom or a C.sub.1 to C.sub.4 alkyl group unsubstituted or substituted with a halogen atom or a hydroxyl, cyano, C.sub.1 to C.sub.4 alkoxy, carboxy, carbamoyl, C.sub.1 to C.sub.4 alkoxycarbonyl, C.sub.1 to C.sub.4 alkylcarbonyloxy, sulfo or sulfamoyl group, A denotes a phenylene group unsubstituted or substituted with one or two members selected from methyl, ethyl, methoxy, ethoxy, chlorine, bromine and sulfo, or a naphthylene group unsubstituted or substituted with one sulfo group, X denotes a halogen atom, and Y is a 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 by the action of an alkali, 0.1 to 10% by weight of .epsilon.
    Type: Grant
    Filed: February 20, 1987
    Date of Patent: October 25, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noriaki Yamauchi, Kunihiko Imada, Shinei Ikeou
  • Patent number: 4780106
    Abstract: Metal-free compounds of the formula ##STR1## 1:1 and 1:2 metal complexes thereof, and acid addition salts of metal-free compounds of said formula and 1:1 and 1:2 metal complexes thereof, whereinB is hydrogen; C.sub.1-4 alkyl; C.sub.1-4 alkyl monosubstituted by C.sub.1-4 alkoxy; C.sub.2-4 alkyl substituted by hydroxy; C.sub.5-6 cycloalkyl; C.sub.5-6 cycloalkyl substituted by 1 to 3 C.sub.1-4 alkyl groups; phenyl(C.sub.1-3 alkyl); phenyl(C.sub.1-3 alkyl) the phenyl group of which is substituted by 1 to 3 substituents selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy and halo; --A--NH--R.sub.2 ; --A'.sub.4 --N(R.sub.7).sub.2 ; --A.sub.4 --N.sup..sym. (R.sub.8).sub.2 R.sub.9 A.sup..crclbar. or --N(R.sub.7).sub.2,R is hydrogen; C.sub.1-4 alkyl; C.sub.5-6 cycloalkyl; C.sub.5-6 cycloalkyl substituted by 1 or 2 C.sub.
    Type: Grant
    Filed: June 10, 1987
    Date of Patent: October 25, 1988
    Assignee: Sandoz Ltd.
    Inventors: Helmut Moser, Manfred Greve, Reinhard Pedrazzi, Roland Wald