Formation Of Azo Group By Coupling Diazonium Compound With Coupling Component At A Specified Ph Range Patents (Class 534/582)
  • Patent number: 5196518
    Abstract: A process for the preparation of azo dyes of formula ##STR1## wherein K is the radical of a coupling component of the benzene or naphthalene series or of the heterocyclic series, and the hydroxy group is attached to K adjacent to the azo group, X is hydrogen or nitro and M is an alkali metal ion, which process comprises coupling a diazo component of formula ##STR2## in the presence of one or more buffer mixtures and in the absence or presence of an alkali metal chloride, to a coupling component of formula ##STR3## in which formulae (2) and (3) K and X are as defined for formula (1). The present invention makes it possible to prepare the azo dyes in high yields.
    Type: Grant
    Filed: August 28, 1991
    Date of Patent: March 23, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Horst Langfeld, Claudio Puebla, Gunter Sereinig
  • Patent number: 5194597
    Abstract: The industrial preparation of C.I. Pigment Yellow 81 by conventional coupling methods has the disadvantage that traces of polychlorinated biphenyls are formed in the course of the reaction of the two components.The invention now provides that the addition of quaternary dialkyldiallylammonium compounds during the azo coupling will decisively suppress the PCB-forming secondary reactions during the pigment synthesis.
    Type: Grant
    Filed: April 30, 1991
    Date of Patent: March 16, 1993
    Assignee: Hoechst AG
    Inventor: Wolfgang Rieper
  • Patent number: 5194598
    Abstract: Azo dyestuffs of the formula ##STR1## in which X denotes H, F, Cl, Br, I, R, CO.sub.2 R, CN, CF.sub.3 and the like,Y/Z denotes H, CH.sub.3, Cl or Br,R.sup.1, R.sup.2 and R denote C.sub.1 -C.sub.4 -alkyl andR.sup.3 and R.sup.4 denote H or CH.sub.3, are highly suitable for the dyeing of polyester fibres, where they are distinguished by a high thermomigration fastness.The preparation of the dyestuffs is preferably carried out by so-called "halogen/cyano exchange".
    Type: Grant
    Filed: February 20, 1991
    Date of Patent: March 16, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventor: Rainer Hamprecht
  • Patent number: 5191070
    Abstract: A continuous process for the preparation of a bisazo pigment mixture of at least two different bisazo pigments of the general formula ##STR1## wherein R.sub.1 and R.sub.2 each may be independent of themselves and are each independently of one another hydrogen, chloro, methyl or methoxy, which bisazo pigments differ from each other in at least one of the substituents R.sub.1 or R.sub.2, by simultaneously coupling a bisdiazotized diaminodiphenyl (A) of formula ##STR2## and a mixture (B) of two coupling components of formula ##STR3## wherein R.sub.1 and R.sub.2 are each independently of the other hydrogen, chloro, methyl or methoxy which coupling components differ from each other at least one of the substituents R.sub.1 or R.sub.
    Type: Grant
    Filed: June 19, 1992
    Date of Patent: March 2, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Werner Guthauser, Philippe Rohner
  • Patent number: 5151129
    Abstract: A process for the production of a pigment composition comprising precipitating a pigment coupling component from alkaline solution by adding to it an acid, in the presence of a pre-formed, water-soluble azo dyestuff; and subsequently coupling the precipitated coupling component, containing the azo dyestuff, with a pigment diazo or tetrazo component, ensuring that at no time is any substantial amount of uncoupled diazo or tetrazo component present, to form a pigment composition containing the water-soluble azo dyestuff.
    Type: Grant
    Filed: March 28, 1991
    Date of Patent: September 29, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Donald J. Morrison, David McGregor, James M. McCrae
  • Patent number: 5142030
    Abstract: Novel dyes are provided having the formula: ##STR1## wherein the R's are the same or different and each is a C.sub.6 -C.sub.12 alkyl.
    Type: Grant
    Filed: August 21, 1991
    Date of Patent: August 25, 1992
    Assignee: Morton International, Inc.
    Inventors: Alejandro Zimin, Michael R. Friswell, Adam E. Verillo
  • Patent number: 5132412
    Abstract: Thiazoleazo dyes of the formula ##STR1## where X is nitrogen or a radical C--R.sup.5, R.sup.5 being cyano, halogen, alkoxycarbonyl or thiocyanato, R.sup.1 is cyano, chlorine, unsubstituted or substituted C.sub.1 -C.sub.6 -alkyl, unsubstituted or substituted phenyl, unsubstituted or substituted thienyl, unsubstituted or substituted pyridyl or unsubstituted or substituted alkylthio, alkylsulfinyl or alkylsulfonyl, R.sup.2 is unsubstituted or substituted alkyl, cycloalkyl, unsubstituted or substituted phenyl, furyl, unsubstituted or substituted thienyl or pyridyl and R.sup.3 and R.sup.4 independently of one another are each unsubstituted or substituted alkyl, or R.sup.3 and R.sup.4, together with the nitrogen atom which links them, form a heterocyclic radical, are used for dyeing textile fibers having good wet fastness and color build-up.
    Type: Grant
    Filed: September 15, 1989
    Date of Patent: July 21, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Guenter Hansen, Gunther Lamm, Helmut Reichelt, Ernst Schefczik
  • Patent number: 5126435
    Abstract: A process for the preparation of azo dyes of formula ##STR1## wherein K is the radical of a coupling component of the benzene or naphthalene series or of the heterocyclic series, and the hydroxy group is attached to K adjacent to the azo group, X is hydrogen or nitro and M is an alkali metal ion or an ammonium ion, which process comprises coupling a diazo component of formula ##STR2## in the presence of a zinc salt and in an inert gas atmosphere, to a coupling component of formula ##STR3## in which formula (2) and (3) above K and X are as defined for formula (1). The process makes it possible to obtain the azo dyes in high yield.
    Type: Grant
    Filed: October 11, 1990
    Date of Patent: June 30, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans P. Joswig, Werner Huber
  • Patent number: 5116955
    Abstract: There is disclosed a process for coupling one or more different diazo components with resorcinol on an industrial scale. The process comprises adjusting and stabilizing the coupling pH of the resorcinol prior to the reaction with the aid of a buffer system and keeping it constant during the coupling reaction or reactions by controlling the ratio of flow of the streams of the diazo component or components and the base. The process makes it possible to prepare mono- and polyazo dyes in excellent uniform quality and yield.
    Type: Grant
    Filed: September 25, 1990
    Date of Patent: May 26, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Horst Langfeld, Roland Minges
  • Patent number: 5086168
    Abstract: The invention relates to monoazo pigments prepared from dichloroanilines as diazo components and CH-acidic coupling components of the acetoacetarylamide or naphthol series, these pigments only containing an extremely low level of polychlorinated biphenyls (PCBs) (at most 25 .mu.g per g of pigment).The process for preparing the pigments takes the form of an azo coupling in an aqueous medium, whereina) azo coupling is effected by adding the diazonium salt solution to a suspension or solution of the coupling component or by simultaneously metering the aqueous suspensions or solutions of the diazonium salt and of the coupling component into the reaction mixture,b) azo coupling is effected at a pH or within a pH range of less than pH 7 andb1) between pH 4 and 7 during and after azo coupling less than 0.
    Type: Grant
    Filed: September 5, 1990
    Date of Patent: February 4, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Wolfgang Rieper
  • Patent number: 5079347
    Abstract: Disazo compounds conforming to a general formula (1) shown below which have fiber-reactive dye properties and dye hydroxy- and/or carboxamido-containing fiber materials, such as wool and in particular cellulose, in strong fast shades. ##STR1## where R is a hydrogen atom or a sulfo group,R.sup.1 is a hydroxy group, a methoxy group or an ethoxy group,M is a hydrogen atom or an alkali metal,X is a chlorine atom or a fluorine atom,Y is a chlorine atom or an amino group or a group of the general formula (2) ##STR2## where R* is a hydrogen atom or a methyl or ethyl group,n is zero, 1 or 2,R.sup.2 is a hydrogen atom or a sulfo group or a .beta.-sulfatoethylsulfonyl group or a vinylsulfonyl group, andR.sup.3 is a sulfo group or a .beta.-sulfatoethylsulfonyl group or a vinylsulfonyl group,it being possible for R.sup.2 and R.sup.3 to be identical to or different from each other.
    Type: Grant
    Filed: December 6, 1988
    Date of Patent: January 7, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Holger M. Buch
  • Patent number: 5066791
    Abstract: Pyridoneazo dyes of the formula ##STR1## where L is C.sub.2 - or C.sub.3 -alkylene, R is C.sub.1 -C.sub.3 -alkyl and n is 1, 2 or 3, are useful for dyeing polyester fabrics.
    Type: Grant
    Filed: February 14, 1990
    Date of Patent: November 19, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Guenter Hansen, Gunther Lamm, Hermann Loeffler
  • Patent number: 5055565
    Abstract: Compounds according to the general formula ##STR1## in which: D is phenyl, optionally substituted by sulfo, carboxy, alkyl, alkoxy, alkanoylamino and/or chlorine, at least by sulfo or carboxy, or is a sulfosubstituted naphthyl;E is 1,4-phenylene, substituted by alkyl, alkoxy, alkanoylamino, ureido and/or chlorine, or is 1,4-naphthylene optionally substituted by sulfo;K is 1,4-phenylene, substituted by alkyl, alkoxy, alkanoylamino, ureido and/or chlorine, or is a 1,4-naphthylene optionally substituted by sulfo;A is a direct bond or is methylene or is a bivalent amino, alkylamino or (.beta.-cyanoethyl)-amino group;Y is vinyl or .beta.-chloroethyl.These compounds are fiber-reactive and have dyestuff properties and dye hydroxy--and/or carboxamido-containing material, in particular fiber material such as wool and, in particular cellulose, in strong color-fast shades.
    Type: Grant
    Filed: August 20, 1990
    Date of Patent: October 8, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Springer, Manfred Kuhn, Werner H. Russ, Ludwig Schlafer
  • Patent number: 5053494
    Abstract: A polyazo compound of the following formula, ##STR1## wherein F is a bisazo or trisazo dye moiety, R.sub.1, R.sub.2 and R.sub.3 are independently of one another are each hydrogen or alkyl, B.sub.1 and B.sub.2 independently of one another are each phenylene or naphthylene, Y.sub.1 and Y.sub.2 independently of one another are each --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 L in which L is group capable of being split by the action of an alkali. The compound is useful for dyeing or printing fiber materials to give dyed or printed products with superior dye performance such as build-up property.
    Type: Grant
    Filed: October 20, 1989
    Date of Patent: October 1, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takashi Omura, Naoki Harada, Hirokazu Sawamoto
  • Patent number: 5047514
    Abstract: Reactive dyes which contain at least one radical of the formula--SO.sub.2 --CH.dbd.CH.sub.2 (1a)or--SO.sub.2 --CH.sub.2 CH.sub.2 --X (1b)and at least one radical of the formula ##STR1## in which X is an inorganic or organic radical detachable under alkaline conditions, R is hydrogen or substituted or unsubstituted C.sub.1-4 -alkyl, Y is oxygen or sulfur and R.sub.1 is a substituted or unsubstituted aliphatic radical, give dyeings or prints having good fastness properties.
    Type: Grant
    Filed: November 5, 1987
    Date of Patent: September 10, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Scheibli, Karl Seitz
  • Patent number: 5047517
    Abstract: The invention relates to a yellow monoazo pigment which is obtained by diazotization of 2-amino-4-chloro-5-methylbenzene-1-sulfonic acid, coupling of the diazonium compound with 1-(3'-sulfophenyl)-3-methyl-5-pyrazolone and subsequent laking of the coupling product to the calcium salt.The new pigment has excellent heat stability and bleeding fastness and good light stability. It is particularly suitable for the pigmenting of polymeric plastics in the mass.
    Type: Grant
    Filed: September 28, 1989
    Date of Patent: September 10, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Walter Deucker
  • Patent number: 5047515
    Abstract: Monoazo compounds which conform to the general formula (1) given below and are used as fiber-reactive dyes for dyeing carboxamido-containing and/or hydroxy-containing materials, for example wool, synthetic polyamide fibers and in particular cellulose fibers, in fast, predominantly yellowish red, red and orange shades.
    Type: Grant
    Filed: May 21, 1990
    Date of Patent: September 10, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Springer, Kurt Hussong
  • Patent number: 5026830
    Abstract: Process for the preparation of azo dyes of the formula ##STR1## in which K is the radical of a coupling component of the benzene or naphthalene series or of the heterocyclic series in which the hydroxyl group is attached to K in a position adjacent to the azo group, X is hydrogen or nitro and M is an alkali metal ion or ammonium ion, which comprises coupling a diazo component of the formula ##STR2## in the presence of an alkali metal chloride and ammonium chloride with a coupling component of the formula (3) ##STR3## K and X in the formulae (2) and (3) being as defined under formula (1). The present invention allows the preparation of the said azodyes in high yields.
    Type: Grant
    Filed: August 29, 1988
    Date of Patent: June 25, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Horst Langfeld, Claudio Puebla, Gunter Sereinig
  • Patent number: 5023326
    Abstract: Reactive dyes of the formula ##STR1## in which Y is hydrogen or sulfo, U is --CN, --CONH.sub.2, --SO.sub.3 H, --OH or --OSO.sub.3 H, D is a phenyl or naphthyl radical, which can be substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl and sulfo, and which contains at least one reactive radical bound direclty or via a bridge member to a ring carbon atom, or to which a further radical is bound which contains a reactive radical, and u is the number 2, 3, 4 or 5, are suitable in particular for the dyeing or printing of cellulose-containing fiber materials by the exhaust method or by the continuous method and product in combination with a high colorisitc yield dyeings and prints which have good fastness properties.
    Type: Grant
    Filed: November 9, 1989
    Date of Patent: June 11, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Herbert Seiler
  • Patent number: 5021559
    Abstract: Water-soluble azo compounds of the general formula D--N.dbd.N--K are described, which have advantageous fiber-reactive dye properties and dye carboxamido-containing and in particular hydroxy-containing materials, such as wool and in particular cellulose fiber materials, in hues which have high color strength and good fastness properties.In the formula D--N.dbd.N--K, the symbols have the following meanings:D is a radical of the general formula ##STR1## in which Y is a vinyl group or an ethyl group which can be eliminated in the .beta.
    Type: Grant
    Filed: May 21, 1990
    Date of Patent: June 4, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Springer, Uwe Reiher
  • Patent number: 5011917
    Abstract: A process for the preparation of a pH-stabilized, liquid, aqueous dyestuff composition of the lithium azo dyestuff of formula (1) ##STR1## which composition has an Na-content of less than 0.2% b.w., based on the lithium azo compound of formula (1), in which process the lithium salt of 4-(.beta.-sulfatoethylsulfonyl)-aniline is diazotized in a mineral acid aqueous solution or in a mineral acidic solution containing a watermiscible organic solvent by means of an essentially sodium-free derivative of nitrous acid as the diazotizing agent, such as nitrosyl sulfuric acid, and the diazotized aniline is coupled in said solution with the lithium salt of 1-hydroxy-7-acetylamino-naphthalene-3-sulfonic acid and a buffering substance for adjusting and maintaining the pH of the composition at a value between 3 and 6.5 is added to that solution subsequent to the above-mentioned diazotizing step or preferably during said or subsequent to said coupling step, the amount of the buffering substance added is from 0.5 to 5% b.w.
    Type: Grant
    Filed: October 10, 1989
    Date of Patent: April 30, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Konrad Opitz, Marcos Segal
  • Patent number: 5010180
    Abstract: Water-soluble azo compounds corresponding to the general formula D--N.dbd.N--K which have advantageous fiber-reactive dyestuff properties and dye materials containing carboxamide groups and in particular materials containing hydroxy groups, such as wool and in particular cellulose fiber materials, in deep fast shades are described.In the formula D--N.dbd.N--K:D is a radical of the general formula ##STR1## in which Y is the vinyl group or an ethyl group in the .beta.
    Type: Grant
    Filed: February 1, 1990
    Date of Patent: April 23, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Springer, Uwe Reiher
  • Patent number: 5008379
    Abstract: Water-soluble, anionic, chromium complexes of disazo compounds, at least one of the complex-forming disazo compounds being of the formula, ##STR1## in which ##STR2## is the radical of a carboxy group-containing diazo component of the benzene or naphthalene series, the carboxy group being ortho to the azo group and the diazo component being free from other metallizable groups, andB-- is the radical of a diazo component of the benzene or naphthalene series free from metallizable substituents,which complexes contain at least one water-solubilizing group, are in free acid or salt form and are useful for dyeing and printing substrates such as natural and synthetic polyamides, polyurethanes and anodized aluminum, particularly fur-lined leather.
    Type: Grant
    Filed: October 29, 1987
    Date of Patent: April 16, 1991
    Assignee: Sandoz Ltd.
    Inventor: Herbert Holliger
  • Patent number: 5003051
    Abstract: A process for the preparation of azo dyes of the formula ##STR1## in which X is --NH.sub.2 or --OH, A is a benzene or naphthalene radical which can be substituted by nitro, halogen, sulfo, C.sub.2 -C.sub.6 alkanoylamino, C.sub.1 -C.sub.6 -alkoxycarbonylamino, sulfonamido and sulfone groups and B is a benzene radical which is monosubstituted or disubstituted by C.sub.1 -C.sub.6 alkyl, or a naphthalene radical which can be substituted by amino, phenylamino, C.sub.1 -C.sub.6 alkylamino and sulfo, or a 1-phenyl-3-methyl-5-pyrazlone radical which can be substituted by halogen, C.sub.1 -C.sub.6 alkyl and C.sub.1 -C.sub.6 alkoy, these radicals being bound to the azo group in the o-position with respect to the hydroxyl or amino groups, comprises diazotizing in aqueous solution an amine of the formula ##STR2## in the presence of at least one ketone of the formula ##STR3## in which R.sub.1 and R.sub.2, independently of one another, are each C.sub.1 -C.sub.
    Type: Grant
    Filed: August 23, 1989
    Date of Patent: March 26, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Ulrich Schlesinger, Peter Loew, Alois Puntener
  • Patent number: 5003053
    Abstract: Water-soluble monoazo compounds of the general formula (1) which dye in fast, mainly red shades materials which contain carboxamide and/or hydroxy groups, preferably in the form of fibers, in particular cellulose fiber materials. ##STR1## in which: Y is .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-chloroethyl, vinyl or .beta.-sulfatoethyl,M is hydrogen, an alkali metal or an alkaline-earth metal,D is naphthyl which is substituted by sulfo and/or a group of the formula Y--SO.sub.2 --,or is one of the radicals ##STR2## in which M and Y have one of the above meanings, m is the number zero or 1, R.sup.1 is hydrogen, lower alkyl, lower alkoxy or carboxy, and R.sup.2 is hydrogen, lower alkyl, lower alkoxy, sulfo, carboxy, optionally substituted aryl, hydroxy, nitro or halogen,n is the number zero or 1,R is hydrogen or optionally substituted lower alkyl,R* is hydrogen or optionally substituted lower alkyl,X is fluorine or chlorine,B is a group of the formula ##STR3## in which R.sup.
    Type: Grant
    Filed: March 19, 1990
    Date of Patent: March 26, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Springer, Walter Helmling, Ludwig Schlafer, Werner H. Russ
  • Patent number: 5001226
    Abstract: Compounds of the formula ##STR1## 1:1 and 1:2 metal complexes thereof, salts of such compounds and metal complexes and mixture thereof, whereineach of B.sub.1 and B.sub.2 is independently hydroxy or amino,each D is independently ##STR2## wherein R is hydrogen, C.sub.1-4 alkyl, C.sub.5-6 cycloalkyl, phenyl, benzyl or phenylethyl,R.sub.1 is hydrogen, cyano, --COOR.sub.4, --CONR.sub.5 R.sub.6, --SO.sub.2 NR.sub.5 R.sub.6, ##STR3## wherein each R.sub.3 is independently hydrogen, C.sub.1-4 alkyl, --NR.sub.5 R.sub.6 or --CONR.sub.5 R.sub.6,R.sub.4 is C.sub.1-6 alkyl or phenyl(C.sub.1-3 alkyl),R.sub.7 is C.sub.1-4 alkyl,R.sub.8 is hydrogen or C.sub.1-4 alkyl, andR.sub.9 is --S--, --O-- or --NR.sub.5 --,R.sub.2 is hydrogen, hydroxy or C.sub.1-4 alkoxy,R.sub.2a is hydrogen, C.sub.1-4 alkyl or halo,M is hydrogen; C.sub.1-8 alkyl; (C.sub.1-4 alkoxy)C.sub.1-4 alkyl; C.sub.2-4 hydroxyalkyl; C.sub.5-6 cycloalkyl; C.sub.5-6 cycloalkyl substituted by 1 to 3 C.sub.1-4 alkyls; phenyl(C.sub.1-3 alkyl); phenyl (C.sub.
    Type: Grant
    Filed: December 19, 1989
    Date of Patent: March 19, 1991
    Assignee: Sandoz Ltd.
    Inventors: Helmut A. Moser, Roland Wald
  • Patent number: 4997939
    Abstract: A process for preparing adenine by reacting an arylazomalononitrile with formic acid or its derivatives in the presence of ammonia and then subjecting the intermediate pyrimidine derivative to a reaction under catalytic reduction condition. Adenine can be prepared in high purity and high yields without isolating the intermediate pyrimidine derivative, when ammonia is removed before conducting the reaction under catalytic reduction condition. Also, the preparation of adenine in high purity and high yields can be more surely attained, when the arylazomalononitrile prepared under a specific condition is employed as a starting material or when Raney nickel is employed as a reduction catalyst in combination with active carbon. The produced adenine is effectively purified by separation of insoluble materials from an aqueous hot solution of adenine adjusted to pH 7.5 to 9.0 and formation of a mineral acid salt of adenine followed by decoloration by heating in the presence of active carbon.
    Type: Grant
    Filed: March 15, 1989
    Date of Patent: March 5, 1991
    Assignee: Kohjin Co., Ltd.
    Inventor: Jiro Suzuki
  • Patent number: 4996304
    Abstract: Reactive dyes of the formula ##STR1## in which D is the radical of a dye of the polyazo or metal complex azo 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: February 23, 1990
    Date of Patent: February 26, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanassios Tzikas
  • Patent number: 4996302
    Abstract: A process for the preparation of polyazo dyes is described which comprises(a) diazotizing a compound of the formula ##STR1## and coupling the product onto a compound of the formula ##STR2## (b) diazotizing a compound of the formula ##STR3## and coupling the product onto the product obtained according to (a); (c) diazotizing a compound of the formula ##STR4## and coupling the product onto the product obtained according to (b); (d) if desired, coupling of a further diazotized compound of the formula (3) onto the product obtained according to (c); and(e) if desired, metallizing the product obtained according to (c) or (d); and in which the symbols are as defined in claim 1. The polyazo dyes obtainable by the process are suitable for dyeing a wide range of textile and non-textile materials and, in particular, for dyeing leather.
    Type: Grant
    Filed: December 7, 1988
    Date of Patent: February 26, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Horst Langfeld
  • Patent number: 4994561
    Abstract: A process for the preparation of an azo dye of formula ##STR1## wherein K is the .beta.-naphthol radical, X is hydrogen or nitro and M is an alkali metal ion or an ammonium ion, which process comprises coupling an aqueous solution containing 15 to 30 percent by weight of a diazo component of formula ##STR2## and 6 to 20 mol % of an ammonium salt, based on the molar amount of the diazo component, at a pH in the range from 10.5 to 11.5 and in an inert gas atmosphere, to a coupling component of formula ##STR3## in which formulae (2) and (3) above K and X are as defined for formula (1).The present invention makes it possible to obtain the claimed azo dyes in high yield.
    Type: Grant
    Filed: June 8, 1990
    Date of Patent: February 19, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans P. Joswig, Werner Huber
  • Patent number: 4988803
    Abstract: An azo dyestuff of the formula ##STR1## in which u and v=H or SO.sub.3 H and u.noteq.v,R=H, unsubstituted C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkyl substituted by OH, halogen, SO.sub.3 H or OSO.sub.3 H,m=0 or 1 and ##STR2## in which R.sub.1 =H, unsubstituted C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -alkyl substituted by OH, OSO.sub.3 H, SO.sub.3 H or COOH. Such dye is particularly suitable for producing on cotton red dyeings and prints having excellent fiber-dyestuff bond stability, stability to oxidizing agents and wash-off properties.
    Type: Grant
    Filed: January 5, 1990
    Date of Patent: January 29, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Frank M. Stohr, Hermann Henk, Karl-Josef Herd
  • Patent number: 4988804
    Abstract: Polyazo dyes obtainable by(a) diazotizing 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid and coupling onto a compound of the formula ##STR1## (b) coupling a diazotized compound of the formula ##STR2## onto the monoazo dye thus obtained, (c) coupling a diazotized compound of the formula ##STR3## onto the product obtained as per (b), and (d) if desired metallizing the product obtained as per (c), the symbols in the formulae being as defined in claim 1, are suitable for dyeing a wide range of textile and nontextile materials, in particular leather.
    Type: Grant
    Filed: October 31, 1988
    Date of Patent: January 29, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Horst Langfeld
  • Patent number: 4988805
    Abstract: The dyestuffs of the general formulae ##STR1## and salts thereof whereinX denotes hydrogen, alkoxy or NHR.sub.3,R denotes hydrogen, alkyl or alkoxy,R.sub.1 denotes alkyl,R.sub.2 and R.sub.3 denote hydrogen, alkyl, alkylcarbonyl, alkylsulphonyl, aryl, arylcar=bonyl, arylsulphonyl, aralkyl, aralkylcarbonyl or aminocarbonyl andm and n denote 1 or 2, andwherein the substituents mentioned can, in turn, be substituted by nonionic radicals or carboxylic or sulphonic acid groups customary in dyestuffs chemistry, are used for dyeing cellulose-containing materials and leather.
    Type: Grant
    Filed: July 14, 1988
    Date of Patent: January 29, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus Kunde
  • Patent number: 4975539
    Abstract: Water-soluble azo compounds which have fiber-reactive and dye properties and dye carboxamido- and/or hydroxyl-containing materials, such as fiber materials, in particular cellulose fiber materials, in strong, predominantly bluish red to orange hues which have good fastness properties; they conform to the general formula (1) ##STR1## in which the symbols have the following meaning: M is a hydrogen atom or an alkali metal,T is a covalent bond or a methylene group or an amino group --N(R)--, in which R is alkyl of 1 to 4 carbon atoms,D is a group of the formula ##STR2## in which R.sup.1 is alkyl of 1 to 4 carbon atoms, hydroxy, nitro, hydrogen, alkoxy of 1 to 4 carbon atoms, chlorine, bromine or carboxy,R.sup.2 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, chlorine or sulfo,R.sup.3 is hydrogen or sulfo,k is the number zero or 1,p is the number zero, 1 or 2 andM has the abovementioned meaning;m is the number zero, 1 or 2;W has one of the meanings of T;X is vinyl, .beta.-chloroethyl, .
    Type: Grant
    Filed: August 31, 1989
    Date of Patent: December 4, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ludwig Schlafer, Werner H. Russ
  • 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: 4975540
    Abstract: Disazo compounds conforming to the general formula (1) below and suitable for use as fiber-reactive dyes for the dyeing of carboxamido-containing and/or hydroxy-containing materials such as wool and, in particular, cellulose fiber materials, in navy hues having good fastness properties ##STR1## in which M is a hydrogen atom or an alkali metal or alkaline earth metal,D.sup.1 is a phenyl radical which can be substituted by substituents from the group consisting of chlorine, bromine, sulfo, alkyl and alkoxy and additionally by a vinylsulfonyl or .beta.-sulfatoethylsulfonyl group or by a group of the general formula (3) ##STR2## where X is a vinyl or .beta.-sulfatoethyl group; D.sup.2 is a radical of the general formula (4) ##STR3## in which M and X have one of the abovementioned meanings and the amino group --NH-- is bound to the benzene ring in the para-position with respect to the sulfo group --SO.sub.3 M or in the paara-position with respect to the free bond.
    Type: Grant
    Filed: January 19, 1989
    Date of Patent: December 4, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Reinhard Hahnle, Hartmut Springer
  • Patent number: 4968784
    Abstract: Disazo compounds represented by the following formula (I): ##STR1## in which R.sub.1 and R.sub.2 are hydrogen, C.sub.1-3 alkyl, C.sub.1-4 alkoxy C.sub.1-3 alkyl, phenyl C.sub.1-3 alkyl, phenoxy C.sub.1-3 alkyl, hydroxy C.sub.1-3 alkyl, cyano C.sub.1-3 alkyl, C.sub.1-4 alkoxyhydroxy C.sub.1-3 alkyl or hydroxyphenoxy C.sub.1-3 alkyl,R.sub.3 is C.sub.1-4 alkyl,R.sub.4 is methyl or ethyl,R.sub.5 is hydrogen, chlorine, methyl or methoxy,n is 2 or 3 respectivelyin the form of the free acid is disclosed and these present compounds are used for dyeing of various fibre materials, leather, wood, pulp and paper etc. in black shade and preparing of black ink for ink-jet, felt-pen and signpen etc. The present compounds have high color value, high affinity and high dyeing velocity on paper and excellent fastnesses.
    Type: Grant
    Filed: May 31, 1989
    Date of Patent: November 6, 1990
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Hidenori Imai, Masahiro Hiraki, Yoshiaki Shimizu
  • Patent number: 4963661
    Abstract: Water-soluble monoazo compounds according to the general formula (1) below having valuable fiber-reactive dyestuff properties which dye carboxamido- and/or hydroxy-containing materials, in particular cellulose fibers, in fast yellow to orange hues. ##STR1## in which the symbols denote: M is hydrogen or an alkali metal,R.sup.1 is hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine, bromine, carboxy or sulfo,R.sup.2 is hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine, or bromine,R is carboxy or lower carbalkoxy,n is the number zero or 1,X and Y independently of each other are each .beta.-thiosulfatoethyl or .beta.-sulfatoethyl or vinyl, however, in the case of X and/or Y being equal to vinyl the index n must be 1.
    Type: Grant
    Filed: May 24, 1988
    Date of Patent: October 16, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Horst Tappe, Dieter Oehme, Ludwig Schlafer, Werner H. Russ
  • Patent number: 4962191
    Abstract: Dyes suitable for dyeing a wide range of textile and non-textile materials, in particular for dyeing leather and pelts, having, in the form of the free acid, the formula ##STR1## wherein D.sub.1 and D.sub.2 are each independently of the other the radical of a diazo component of the benzene or naphthalene series which carries a hydroxy or carboxy in ortho-position to the azo group and which may or may not be further substituted,K is the radical of a coupling component of the benzene or naphthalene series or of the heterocyclic series which carries the group X in ortho-position to the azo group and which may or may not be further substituted,Me is chromium or cobalt,Q is an unsubstituted or substituted phenyl or naphthyl radical or an unsubstituted or substituted aromatic-heterocyclic radical,R.sub.1 is unsubstituted or substituted C.sub.1 -C.sub.6 alkyl or unsubstituted or substituted phenyl,R.sub.2 is hydrogen or independently has the meaning of R.sub.1, X is --O-- or --NR.sub.3,R.sub.3 is hydrogen or C.sub.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: October 9, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Alois Puntener, Kurt Burdeska
  • Patent number: 4960872
    Abstract: Water-soluble monoazo compounds corresponding to the following general formula (1) which have valuable fiber-reactive dyestuff properties and which dye materials, in particular cellulose fibers, containing carboxamide and/or hydroxy groups in fast, yellow shades. ##STR1## in which the symbols have the following meanings: D is a benzene ring or a radical of the formula ##STR2## R.sup.1 and R.sup.3, independently of one another, are both hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine, bromine, carboxy or sulfo,R.sup.2 and R.sup.4, independently of one another, are each hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine or bromine,R is carboxy or lower carboalkoxy, andX and Y, independently of one another, are each .beta.-thiosulfatoethyl or .beta.-sulfatoethyl or vinyl, but, in the event that x and/or Y is vinyl, the radicals R.sup.1 and/or R.sup.2 are necessarily sulfo.
    Type: Grant
    Filed: February 3, 1988
    Date of Patent: October 2, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ludwig Schlafer, Gunther Schwaiger, Werner H. Russ
  • Patent number: 4952678
    Abstract: Trisazo dyes of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are identical or different and each, independently of the others, is hydrogen, methyl, ethyl, methoxy or chlorine, R.sup.5 is C.sub.2 -C.sub.4 -alkyl, X is C.sub.1 -C.sub.24 -mono- or dialkylamino, monobenzylamino, mono-(phenyl-ethyl)-amino, monophenylamino, N-(C.sub.1 -C.sub.12 -alkyl)-N-benzylamino, N-(C.sub.1 -C.sub.12 -alkyl)-N-(phenylethyl)amino or N-(C.sub.1 -C.sub.12 -alkyl)-N-phenylamino or each of the phenyls substituted by C.sub.1 -C.sub.12 -alkyl, cyclo-hexyl, 4-(C.sub.1 -C.sub.12 -alkyl)cyclohexyl, C.sub.1 -C.sub.24 -alkyloxy, phenoxy or C.sub.1 -C.sub.24 -alkanoyloxyl, or is OR, where R is C.sub.1 -C.sub.24 -alkyl, unsubstituted or C.sub.1 -C.sub.12 -alkyl-, cyclohexyl-, 4-(C.sub.1 -C.sub.12 -alkyl)cyclohexyl-, C.sub.1 -C.sub.24 -alkoxy-, phenoxy- or C.sub.1 -C.sub.
    Type: Grant
    Filed: October 29, 1987
    Date of Patent: August 28, 1990
    Assignee: BASF Aktiengesellschaft
    Inventor: Karl-Heinz Etzbach
  • Patent number: 4948879
    Abstract: Monoazo compounds conforming to the general formula (1) shown and defined hereinafter have very good fiber-reactive dye properties and dye hydroxy- and/or carboxamido-containing material, in particular fiber material, such as wool and in particular cellulose fibers, in strong fast shades. ##STR1## where the symbols have the following meanings: D is a benzene or naphthalene ring or a heterocyclic radical,R.sup.1 and R.sup.
    Type: Grant
    Filed: November 17, 1988
    Date of Patent: August 14, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Horst Tappe, Dieter Oehme, Werner H. Russ
  • Patent number: 4946947
    Abstract: Water-soluble azo compounds of the general formula D-N=N-K in which D is a radical of the general formula ##STR1## in which Y denotes the vinyl group or is an ethyl group which is substituted in the .beta.-position by a substituent which can be eliminated by means of alkali, R stands for hydrogen, hydroxy, lower alkyl, lower alkoxy, carboxy or halogen, n is the number zero or 1, M is hydrogen or a salt-forming metal atom, and the free bond from the benzene ring to the azo groups is in the meta- or para-position to the nitrogen atom of the benzotriazole radical, and in which K is a radical of a water-soluble coupling component, such as, for example, from the series comprising the aminobenzenes, phenols, naphthols, aminonaphthols, acylaminonaphthols, pyrazolones, aminopyrazoles, acetoacetylarylides and hydroxypyridones.
    Type: Grant
    Filed: June 5, 1989
    Date of Patent: August 7, 1990
    Inventors: Hartmut Springer, Kurt Hussong
  • Patent number: 4940492
    Abstract: Colorant mixtures for use in printing inks contain isoquinoline-azo pigments of the formula I ##STR1## where X is chlorine, bromine, C.sub.1 -C.sub.4 -alkoxy or nitro,n is 1, 2 or 3, and the ring A can be substituted, and an isoquinoline-azo dye of the formula II ##STR2## where Y is C.sub.6 -C.sub.20 -alkoxy which may be interrupted by one or more oxygen atoms, and the ring B can be substituted.
    Type: Grant
    Filed: June 22, 1988
    Date of Patent: July 10, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinrich Kowarsch, Johannes P. Dix
  • Patent number: 4939242
    Abstract: A process for the preparation of the lithium azo compound of the formula ##STR1## having an Na content of less than 0.2% by weight, in particular less than 0.1% by weight, in which the lithium salt of 4-(.beta.-sulfatoethylsulfonyl)-aniline is diazotized in an aqueous solution or in an aqueous solution containing a water-miscible organic solvent by means of nitrosylsulfuric acid, and the product is coupled with the lithium salt of 1-hydroxy-7-acetylaminonaphthalene-3-sulfonic acid.
    Type: Grant
    Filed: March 25, 1988
    Date of Patent: July 3, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Konrad Opitz, Marcos Segal
  • Patent number: 4935502
    Abstract: When a diamine of the formula ##STR1## in which n is 1 to 4, is bis-diazotized and the resulting bis-diazo compound is coupled with 2 moles of one or more coupling components of the formula ##STR2## in which R.sup.1 is hydrogen, chlorine, bromine, methyl or methoxy and R.sup.2 is hydrogen or, if R.sup.1 is hydrogen, also methyl or ethyl, disazo compounds are obtained which are colorants. Due to their high fastness to light and to migration and their heat stability and dispersibility, these compounds are useful for pigmenting high molecular weight materials, especially polyolefins.
    Type: Grant
    Filed: August 22, 1989
    Date of Patent: June 19, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rudolf Kuhne, Heinrich Hamal
  • Patent number: 4929720
    Abstract: Isothiazole dyes of the formula ##STR1## where X is substituted or unsubstituted C.sub.1 -C.sub.8 -alkyl or substituted or unsubstituted phenyl,Y is hydrogen, cyano, chlorine or bromine,R.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,R.sup.2 is hydrogen, cyano, carbamoyl, C.sub.1 -C.sub.4 -monoalkyl- or -dialkyl-carbamoyl, C.sub.1 -C.sub.6 -alkanoyl, C.sub.1 -C.sub.6 -alkoxycarbonyl or 2-(C.sub.1 -C.sub.4 -alkoxy)-ethoxycarbonyl andR.sup.3 is hydrogen, C.sub.1 -C.sub.8 -alkyl which may be substituted and/or interrupted by one or two oxygen atoms, or is C.sub.5 -C.sub.7 -cycloalkyl, C.sub.3 -C.sub.6 -alkenyl or phenyl, are useful for dyeing synthetic fibers.
    Type: Grant
    Filed: November 10, 1988
    Date of Patent: May 29, 1990
    Assignee: Basf Aktiengesellschaft
    Inventors: Guenter Hansen, Ernst Schefczik, Helmut Reichelt
  • Patent number: 4921945
    Abstract: Disazo dyes which are useful for dyeing and printing, of the formula ##STR1## in which: D is the radical of a substituted or unsubstituted, homocyclic or heterocyclic diazo component, V.sup.1 and V.sup.2 independently of one another are hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, halogen or cyano, X is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, halogen, cyano or a group of the formula --NH--CHO, --NH--CO--NH.sub.2, --NH--CO--NH--Q or --NH--CO--(0).sub.m --Q in which m is zero or 1 and Q is substituted or unsubstituted C.sub.1 -C.sub.4 alkyl or phenyl, Z is C.sub.1 -C.sub.4 alkyl--CO--, --CN, --COO--C.sub.1 -C.sub.4 alkyl, --CONH.sub.2 or --CO--C.sub.6 H.sub.5, R.sup.1, R.sup.2 and R.sup.3 independently of one another are in each case a substituted or unsubstituted alkyl radical or R.sup.1 and R.sup.2, together with the nitrogen atom linking them, or R.sup.1, R.sup.2 and R.sup.
    Type: Grant
    Filed: May 25, 1988
    Date of Patent: May 1, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Willy Stingelin
  • Patent number: 4920208
    Abstract: Basic azo dyestuffs of the general formula ##STR1## and tautomers thereof, in which D is the radical of a diazo or tetrazocomponent free of anionic groups,X is O or NH,R.sup.1, R.sup.2 are hydrogen, alkyl or aryl,B is a bridge member andR.sup.3, R.sup.4 are hydrogen, alkyl, alkenyl or aralkyl orR.sup.2 and R.sup.3 together with B and the two nitrogen atoms to which they are bonded form a 5- or 6-membered heterocyclic and in this caseB also stands for a direct bond, orR.sup.3 and R.sup.4 together with the nitrogen atom to which they are bonded form a 5- or 6-membered heterocyclic,n is 1 or 2, and in whichthe cyclic and acyclic radicals can in turn be substituted by radicals customary in dyestuff chemistry, find utility for dyeing and coloring synthetic and natural materials.
    Type: Grant
    Filed: September 28, 1988
    Date of Patent: April 24, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventor: Aloysius Engel
  • Patent number: 4920206
    Abstract: Azo Pigments are made by subjecting a diazo component to an azo coupling reaction with the equivalent quantity of a coupling component difficultly soluble at less than 65.degree. C. in the aqueous/acid and aqueous/neutral pH-ranges. More specifically, an aqueous/acid-solution of the diazo component is continuously mixed at a temperature of less than 65.degree. C. within a period of less than 1 minute with the aqueous/alkaline solution of the coupling component and a predetermined pH between 2 and 9 is established by controlling the flow of the mass streams of diazo component and coupling component; in this way a portion of the coupling component is caused to undergo immediate reaction to the azo pigment to be made whereas the balance portion of the coupling component simultaneously commences precipitating as finely crystalline reactive matter, which is reacted in a post-reaction phase with unreacted diazo component to give the azo pigment to be made.
    Type: Grant
    Filed: March 29, 1989
    Date of Patent: April 24, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Behringer, Heinrich Rehberg