Purification Or Recovery Patents (Class 534/887)
  • Patent number: 5041539
    Abstract: The invention relates to a process for the preparation of concentrated storage-stable aqueous solutions of yellow azo- and azoxystilbene dyes which are obtained by self-condensation of 4-nitrotoluene-2-sulfonic acid in the presence of an alkali metal hydroxide, by converting the sparingly soluble alkali metal salt of the dye into a water-soluble ammonium salt by double cation exchange via a lipophilic ammonium salt, which process comprises carrying out the double ion exchange in a two-phase system of nitrobenzene/water and using, for the first ion exchange a di- or trialkylamine containing a total of 12 to 40 carbon atoms and, for the second ion exchange, a mono-, di- or trialkanolamine containing 2 to 4 carbon atoms in each alkyl moiety.The concentrated storage-stable dye solutions so obtained are particularly suitable for dyeing paper.
    Type: Grant
    Filed: June 19, 1989
    Date of Patent: August 20, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Paul Herzig, Jurgen Markert
  • Patent number: 5041540
    Abstract: Novel copper formazan reactive dyes which contain one or two chromophoric radicals derived from a copper formazan of the formula ##STR1## where R.sup.1 is hydrogen, hydroxysulfonyl, C.sub.1 -C.sub.4 -alkoxy or chlorine, R.sup.2 is hydrogen or hydroxysulfonyl and one of the two radicals R.sup.3 and R.sup.4 is hydrogen and the other is hydroxysulfonyl or, if at least one of the two radicals R.sup.1 and R.sup.2 is hydroxysulfonyl, R.sup.3 and R.sup.4 can each at the same time also be hydrogen, and two or three halotriazine radicals as reactive system, and salts thereof, are useful for dyeing or printing hydroxyl- or nitrogen-containing organic substrates.
    Type: Grant
    Filed: November 3, 1989
    Date of Patent: August 20, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Pandl, Manfred Patsch
  • Patent number: 5037967
    Abstract: Disperse dyes containing a monoazo coupling component of the formula ##STR1## in which X is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, acylamino, halogen or a group of the formula --NH--CO--NHQ in which Q is hydrogen, C.sub.1 -C.sub.4 alkyl or phenyl,Y is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkoxy,R is hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.12 alkenyl or phenyl, or Y and R, together with the nitrogen atom and the two C atoms linking them, form a 5-membered or 6-membered ring,B is a linear or branched C.sub.2 -C.sub.6 alkylene radical,W is halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy,Z is halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or nitro andm and n are each 0, 1, 2 or 3.
    Type: Grant
    Filed: November 7, 1989
    Date of Patent: August 6, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Angelo D. Casa, Peter Liechti, Max Dempfle
  • Patent number: 5037966
    Abstract: Dyes of the formula ##STR1## where R and R.sub.1 are independently of the other hydrogen, halogen, nitro, alkyl or alkoxy and KK is the radical of a coupling component, which are particularly suitable for dyeing polyester fibers if no water-solubilizing group is present, and which are particularly suitable for dyeing and printing textile materials made of polyamide fibers when at least one sulfo group is present in the dye.
    Type: Grant
    Filed: February 28, 1990
    Date of Patent: August 6, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Naef
  • Patent number: 5037963
    Abstract: The preparation of symmetrical azodinitriles prepared from keto acids is disclosed. A keto acid of the formula ##STR1## is reacted with M(CN).sub.x and an ammonia source to obtain an aminonitrile metal carboxylate of the formula ##STR2## The aminonitrile metal carboxylate is reacted with M.sub.1 (OCl).sub.x with the proviso that no alcohol or surface active agent is utilized to form a metal salt of an azo compound. This metal salt is reacted with mineral acid to give the symmetrical azodinitrile compound of the formula ##STR3## R.sub.1 is an alkyl group containing from 1 to about 12 carbon atoms and R.sub.2 is an alkylene group containing from 1 to about 12 carbon atoms. M is a metal comprising lithium, sodium, potassium, magnesium or calcium; M.sub.1 is a metal comprising sodium, potassium or calcium; and x is the valence of M and M.sub.1.
    Type: Grant
    Filed: December 26, 1989
    Date of Patent: August 6, 1991
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 5037965
    Abstract: A monoazo compound represented by the following formula in the free acid form, ##STR1## wherein D is phenylene or naphthylene, R is hydrogen or alkyl, A is phenylene or naphthylene, Z.sub.1 and Z.sub.2 independently of one another are each vinylsulfonyl, .beta.-sulfatoethylsulfonyl and the like, and X is pyridinio or amino represented by the following formula ##STR2## wherein R.sub.1 and R.sub.2 independently of one another are each hydrogen, alkyl, phenyl, naphthyl or benzyl, which is useful for dyeing or printing fiber materials to give dyed or printed products of red color excellent in fastness properties with excellent build-up, level-dyeing and washing-off properties.
    Type: Grant
    Filed: November 21, 1988
    Date of Patent: August 6, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshihiko Morimitsu, Kingo Akahori, Yutaka Kayane, Naoki Harada, Takashi Omura
  • Patent number: 5037962
    Abstract: The .beta.-modification, which is stable under dyeing conditions, of the dyestuff of the formula ##STR1## is prepared by heating the .alpha.-modification, which is unstable under dyeing conditions, at temperatures of 60.degree. to 180.degree. C. and the .beta.-modification is useful in printing and dyeing fiber materials of cellulose esters, synthetic linear polyesters or mixed fabrics of the polyester fiber material with wool or viscose staple.
    Type: Grant
    Filed: August 21, 1989
    Date of Patent: August 6, 1991
    Assignee: Cassella AG
    Inventors: Hubert Kruse, Ulrich Buhler, Konrad Opitz, Willi Steckelberg
  • Patent number: 5028701
    Abstract: Disperse dyestuffs of the formula ##STR1## in which A/B denotes H, alkyl, C1 or O-alkyl,R.sub.1, R.sub.2, R.sub.3 denote H or alkyl,R.sub.4 denotes alkyl, aryl or COO-alkyl,R.sub.5 denotes alkyl or aryl,Y denotes H or CN,X denotes NO.sub.2, Cl, Br, CN or SO.sub.2 -alkyl,V denotes NO.sub.2, Cl, Br, COOR.sub.5, COR.sub.5 CF.sub.3 or alkyl andZ denotes H, Cl, Br, SCN or CN,are very color-strong and are suitable in particular for the dyeing of polyester by a wide range of methods.
    Type: Grant
    Filed: June 15, 1989
    Date of Patent: July 2, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Hamprecht, Manfred Hoppe
  • Patent number: 5026831
    Abstract: The invention relates to compounds of the formula (I) ##STR1## where D.sup.1 and D.sup.2 are each independently of each other unsubstituted or substituted aryl or hetaryl. The compounds are obtained by diazotizing one or more amines of the formula D-NH.sub.2 where D has the meaning D.sup.1 or D.sup.2 as per the formula (I) and coupling with 0.5 mole of 1,5-diazabicyclo[3.3.0]octane-2,4,6,8-tetrone per mole of total reacting diazonium salts. Depending on the presence and length of alkyl chains the compounds are suitable for use as pigments, disperse dyes or even fat dyes.
    Type: Grant
    Filed: November 10, 1988
    Date of Patent: June 25, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rudiger Jung, Reinhold Deubel
  • 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: 5023274
    Abstract: The fibre-reactive formazan dyes of the formula ##STR1## where X is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, cyano or nitro, Y is .beta.-haloethyl or vinyl, m is 1, 2 or 3, n is 3 or 4, p is 0, 1 or 2 and q is 0 or 1, produce dyeings having good fastness properties on nitrogen-containing or hydroxyl-containing fibre materials.
    Type: Grant
    Filed: April 25, 1989
    Date of Patent: June 11, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Alois Puntener, Urs Lehmann, Peter Scheibli, Josef Koller
  • 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: 5015731
    Abstract: Copper complex formazan compounds which have fiber-reactive properties and are very highly suitable for use as dyes for dyeing carboxamido-containing and/or hydroxy-containing material, such as fiber material, for example wool and cellulose fiber materials, have the general formula (1) ##STR1## where A is a benzene or naphthylene ring which may be substituted by substituents customary in dyes, such as halogen, nitro, alkyl and alkoxy,B is alkylene of 1 to 8 carbon atoms or alkenylene of 2 to 8 carbon atoms which may each be substituted by phenyl which in turn may contain the substituents customary in dyes, or is alkylene-phenylene or alkenylene-phenylene having lower alkylene and alkenylene radicals, while the phenylene radicals may in turn contain the substituents customary in dyes, or is a phenylene or naphthylene radical which may contain substituents customary in dyes, or is the bivalent radical of a heterocycle, such as furan, thiophene or benzimidazole, or--B--Z together is hydrogen,Z is a water-solubil
    Type: Grant
    Filed: February 2, 1990
    Date of Patent: May 14, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunther Schwaiger, Hartmut Springer
  • Patent number: 5013826
    Abstract: The azo dyes of the formula ##STR1## in which R.sub.1 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.10 alkyl, R.sub.2 is a group of the formula, --CN, --CON(R.sub.8)R.sub.9, --COR.sub.10, --COOR.sub.11, --SO.sub.2 R.sub.12 or --CONHNHR.sub.13, R.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.6 alkanoylamino, C.sub.1 -C.sub.10 alkoxy or phenoxy, R.sub.4 is substituted or unsubstituted C.sub.1 -C.sub.10 alkyl, R.sub.5 is C.sub.1 -C.sub.4 alkyl, R.sub.6 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.7 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.8, R.sub.9 and R.sub.13, independently of one another, are hydrogen or substituted or unsubstituted C.sub.1 -C.sub.10 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or naphthyl, R.sub.10, R.sub.11 and R.sub.12 are substituted or unsubstituted C.sub.1 -C.sub.10 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or naphthyl, X is an oxygen atom or a group of the formula --CH(R.sub.14)-- in which R.sub.14 is hydrogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: May 7, 1991
    Assignee: Ciba-Giegy Corporation
    Inventor: Harald Walter
  • Patent number: 5010179
    Abstract: The preparation of mixed, symmetrical azonitrile initiators prepared from keto acids and aminonitrile is disclosed. A keto acid of the formula ##STR1## is reacted with M(CN).sub.x and an ammonia source to obtain an aminonitrile metal carboxylate of the formula ##STR2## The aminonitrile metal carboxylate is reacted with M.sub.1 (OCl).sub.x in the presence of a surfactant to form an azonitrile metal carboxylate. The excess M.sub.1 (OCl).sub.x is reacted with an aminonitrile of the formula ##STR3## in the presence of the surfactant to form a symmetrical azonitrile initiator ##STR4## The aminonitrile metal carboxylate is reacted with mineral acid to give the symmetrical azonitrile compound of the formula ##STR5## R.sub.1 is an alkyl group containing from about 1 to about 12 carbon atoms and R.sub.2 is an alkylene group containing from 1 to about 12 carbon atoms. M is a metal comprising lithium, sodium, potassium, magnesium or calcium; M.sub.
    Type: Grant
    Filed: December 26, 1989
    Date of Patent: April 23, 1991
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • 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: 5010178
    Abstract: Disclosed are processes for the preparation of mixed azodinitriles initiators of the formulae ##STR1## These initiators are prepared by reacting a keto acid of the formula ##STR2## with M(CN).sub.x, a hydrazine source, a ketone of the formula ##STR3## and hydrochloric acid to form ##STR4## The hydrazo intermediates are reacted with chlorine gas in the presence of acetone solvent to oxidize the mixture of hydrazo intermediates to the mixed azonitrile initiators. R.sub.1 is an alkyl group containing from about 1 to about 12 carbon atoms, R.sub.2 is non-existent or an alkylene group containing from 1 to about 12 carbon atoms, or a cycloalkylene or alkyl cycloalkylene group containing from about 3 to about 12 carbon atoms, R.sub.3 and R.sub.4 are alkyl groups containing from 1 to about 12 carbon atoms, or one of R.sub.3 and R.sub.4 is an alkoxy group containing from 1 to about 4 carbon atoms and M is a metal comprising lithium, sodium, potassium, magnesium, or calcium.
    Type: Grant
    Filed: December 26, 1989
    Date of Patent: April 23, 1991
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 5010177
    Abstract: Disclosed are processes for the preparation of an azonitrile initiator having both a low salt and low water content of the formula ##STR1## This initiator is prepared by reacting a keto acid of the formula ##STR2## with M(CN).sub.x, a hydrazine source, and hydrochloric acid to form ##STR3## The hydrazo intermediate is reacted with chlorine gas in the presence of acetone to oxidize the hydrazo intermediate to the azonitrile initiator. After oxidation, the reaction mixture is permitted to separate into layers. The bottom aqueous layer is removed and discarded. The upper acetone-azonitrile initiator level is treated with solid calcium chloride or a saturated calcium chloride or sodium chloride solution. This salting out procedure generates an additional water layer that further contains (M(Cl).sub.x. The final acetone-azonitrile initiator solution has a low salt and low water content.R.sub.1 is an alkyl group containing from about 1 to about 12 carbon atoms, R.sub.
    Type: Grant
    Filed: December 26, 1989
    Date of Patent: April 23, 1991
    Assignee: The B. F. Goodrich Company
    Inventors: John T. Lai, Deborah S. Filla
  • 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: 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: 5001229
    Abstract: Basic dyestuffs of the formula ##STR1## or tautomeric forms thereof, whereinR.sub.1 and R.sub.2 stand for hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen,Q - E stands for C-S, C-O, C-NH or N.sup..sym. -N.sup..crclbar.,A stands for C.sub.1 -C.sub.4 -alkylene,W stands for the radical of an aliphatic mono-, di-, tri-, tetra-, penta-, hexa- or heptamine, which can be protonated or quaternized,n stands for 0 to 1.5 andp stands for 1.3 to 10,are suitable for dyeing materials which can be dyed with basic dyestuffs.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: March 19, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Franke, Peter Wild
  • Patent number: 4997920
    Abstract: Compounds of the formulae I and II ##STR1## in which A is a radical of the formulae III, IV or V ##STR2## R.sub.1 and R.sub.4 are --H or --Cl, R.sub.2 and R.sub.5 are --H, halogen, --NO.sub.2, --CN, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 alkoxy, --CF.sub.3 or phenyloxy which is unsubstituted or substituted by one or two chlorine atoms and/or one or two methyl or methoxy groups, and R.sub.3 is alkyl having at least 10 C atoms, X is a radical of the formulae --NH--, --O--, ##STR3## n is the number 1 or 2, Y is the radical of the formulae --COO--, --OOC--, --CONH-- or --NHCO-- or a radical of the formulae ##STR4## in which R.sub.1 and R.sub.2 are as defined above, D is an aromatic heterocyclic 5- or 6-membered ring, in which the ring contains 1 or 2 N atoms and may additionally contain an O atom or S atom, Z is --H, --Br, --OCH.sub.3, --CN or --NO.sub.2 and X.sub.1 and X.sub.2, independently of one another, are --H, halogen, --CH.sub.3, --OCH.sub.3, --OC.sub.2 H.sub.5 or --NO.sub.2 and X.sub.
    Type: Grant
    Filed: September 11, 1989
    Date of Patent: March 5, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Stefan Hari, Olof Wallquist, Jost von der Crone
  • Patent number: 4997918
    Abstract: Novel cationic azo compounds of the formula ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.4 -alkylene, R.sub.2 is C.sub.1 -C.sub.4 -alkyl, R.sub.3 is C.sub.1 -C.sub.4 -alkyl, R.sub.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, acylamino or halogen, R.sub.5 is hydrogen, C.sub.1 -C.sub.4 - alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen, one or more or R.sub.5 independently of each other being present on the ring to which R.sub.5 is attached, and A is an anion. Also provided is the production, and the use of these novel compounds as dyes for dyeing and/or printing, especially polyacrylonitrile materials, neutral blue dyeings having in particular good fastness to light being obtained.
    Type: Grant
    Filed: May 6, 1987
    Date of Patent: March 5, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Zink
  • Patent number: 4997917
    Abstract: The invention relates to a process for the preparation of asymmetrical 1:2 chromium complex dyes of not less than 90% purity and containing at least one water-solubilizing group, which process comprises reacting a mixture of two metallizable azo dyes that contain different diazo components and different coupling components, or a mixture of a metallizable azo dye and a metallizable azomethine dye, in the molar ratio of 0.85:1.0 to 1.2:1.0, with the proviso that only one of said two mixture components contains at least one water-solubilizing group, with a chromium donor, under pressure and at a temperature above 100.degree. C. and in the pH range from 0 to 2, and subsequently carrying out further reaction in a weakly acid, neutral or weakly alkaline pH range, utilizing a single vessel for all steps.The dyes obtained by the process of the invention are particularly suitable for dyeing wool or polyamide materials.
    Type: Grant
    Filed: March 4, 1985
    Date of Patent: March 5, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Walter Iff, Daniel Parisot, Hans Schaller
  • Patent number: 4996303
    Abstract: The invention relates to a process for the preparation of 1:2 metal complex azo dyes of formula ##STR1## wherein each X is hydrogen, halogen or nitro, K and K' are each independently of the other the radical of a coupling component of the benzene, naphthalene or pyrazolone series, Y and Y' are each --O-- or --N(R), wherein R is hydrogen, C.sub.1 -C.sub.4 alkyl or phenyl, Me is chromium or cobalt and Ka is a cation, and Y and Y' are attached to K and K' adjacent to the azo group, by coupling and metallising, which process comprises coupling, in aqueous solution, a diazo component of formula ##STR2## wherein X is as defined for formula (1), in the presence of the 5- to 30-fold molar amount of sodium and/or potassium chloride, based on the molar amount of diazo component, and in the presence of a compound that donates a chromium or cobalt atom, to coupling components of formulaeHK--YH and HK'--Y'H (3),wherein K, K', Y and Y' are as defined for formula (1).
    Type: Grant
    Filed: November 22, 1988
    Date of Patent: February 26, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Alois Puntener, Daniel Parisot
  • Patent number: 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: 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: 4988802
    Abstract: Reactive dyes which possess three reactive groups and conform to the formula ##STR1## where R.sup.1 is hydrogen, methyl or ethyl,X is hydrogen or hydroxysulfonyl,Hal is fluorine or chlorine,D is phenylene, carboxyl- hydroxysulfonyl-monosubstituted or -disubstituted phenylene or hydroxysulfonylmonosubstituted or -disubstituted naphthylene, andA is a reactive group which reacts only substitutively with the hydroxyl groups of the cellulose, or A--D together are a benzo-fused reactive group which reacts only substitutively with the hydroxyl groups of the cellulose, are used for dyeing or printing hydroxyl- or nitrogen-containing substrates.
    Type: Grant
    Filed: February 23, 1990
    Date of Patent: January 29, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Hermann Loeffler, Manfred Patsch
  • 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: 4985043
    Abstract: Mixtures of monoazo dyes suitable for dyeing and printing hydrophobic fiber materials and mixtures thereof with natural fibers contain one or more dyes of the formula I ##STR1## and one or more dyes of the formula II ##STR2## in which Hal denotes bromo or chloro; R.sup.1 and R.sup.2, independently of one another, denote methyl or ethyl; R.sup.3, R.sup.4, R.sup.5 and R.sup.6, independently of one another, denote linear alkyl having 1 to 4 carbon atoms or alkenyl having 3 or 4 carbon atoms; and R denotes methyl, acetylamino, propionylamino, i-butyrylamino, or n-butyrylamino.
    Type: Grant
    Filed: March 15, 1989
    Date of Patent: January 15, 1991
    Assignee: Cassella Aktiengesellschaft
    Inventors: Ulrich Buhler, Manfred Hahnke, Reinhard Kuhn, Margarete Boos
  • Patent number: 4985545
    Abstract: A water-soluble formazan colorant, which is represented by the following general formula (I) in the form of free acid: ##STR1## (where: R represents a hydrogen atom or a lower alkyl group which may be substituted; X denotes a phenylene group or a naphthylene group which may be substituted; Y indicates --SO.sub.2 CH.dbd.CH.sub.2 group or --SO.sub.2 C.sub.2 H.sub.4 W group wherein W represents a group to be eliminated by the action of alkali; and Z designates a lower alkylamino group, a phenylamino group or a naphthylamino group, having one or two water-soluble groups selected from the group consisting of hydroxyl group, sulfonic acid group and carboxylic acid group); and a method of dyeing by use of the colorant. The colorant is used to dye cellulosic and nitrogen-containing fibers in blue shades with excellent reactive fixing properties.
    Type: Grant
    Filed: August 15, 1988
    Date of Patent: January 15, 1991
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Kiyoshi Himeno, Toshio Hihara, Kanzi Shimizu, Yukiharu Shimizu
  • Patent number: 4985045
    Abstract: A monoazo dyestuff composition comprising at least two different individual compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2, independently of each other, are linear or branched alkyl having 1 to 4 carbon atoms and R is linear or branched alkyl having 1 to 5 carbon atoms, and where said individual compounds differ from each other in at least the R moiety, has improved dyeing properties compared with the individual dyestuffs when used to dye or print hydrophobic fiber materials.
    Type: Grant
    Filed: October 30, 1989
    Date of Patent: January 15, 1991
    Assignee: Cassella Aktiengesellschaft
    Inventors: Ulrich Buhler, Klaus Hofmann
  • Patent number: 4981489
    Abstract: Disazo compounds based on 4,4'-diaminodiphenyl compounds contain not less than 50% by weight of a disazo compound of the general formulaA--N.dbd.N--Z--N.dbd.N--B (I)where Z is a radical of an unsubstituted or symmetrically substituted diphenylene, A is a radical of a coupling component of a 1-phenylpyrazolone or of an acetoacetarylide, where the phenyl and the aryl radical is subtsituted by sulfo or carboxyl groups, and B is a radical of a coupling component based on 1-phenylpyrazolone or acetoacetarylide, which are free of sulfo and/or carboxyl groups.The disazo compounds can be obtained by coupling the tetrazotized diamine H.sub.2 N--Z--NH.sub.2 to the coupling component AH containing an acidic group in a medium containing a mineral acid, and then coupling the product to BH in a buffered medium (pH about 4).The novel disazo compounds are suitable as additives to pigments, in particular azo and disazo pigments, for improving the transparency and heat stability of the pigment particles, and the flow behavior.
    Type: Grant
    Filed: October 23, 1989
    Date of Patent: January 1, 1991
    Assignee: BASF Lacke & Farben Aktiengesellschaft
    Inventors: Wolfgang Ruff, Egon Liedek, Gerhard Berger, Hans W. Sonneborn
  • Patent number: 4980459
    Abstract: The invention describes a process for the preparation of formulations of water-insoluble to sparingly soluble azo dyes by simultaneous diazotization and coupling in a single step reaction, filtering the dye dispersion and, if desired, drying the dyestuff, which process comprises carrying out said simultaneous diazotization and coupling by intimately mixing the aqueous solution or suspension of the reactants, in the presence of one or more surface-active agents, concentrating the dilute dye dispersion by membrane separating methods, and at the same time at least partially removing salt and/or acid from the dispersion and converting it into a storage stable liquid formulation or, by drying, into a solid dye formulation.
    Type: Grant
    Filed: August 14, 1989
    Date of Patent: December 25, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Alberto Rabassa, Beat Bruttel
  • Patent number: 4980458
    Abstract: Mixed crystals of at least two different compounds of formula I ##STR1## wherein R is --CH.sub.3, phenyl, --COOCH.sub.3, --COOCH.sub.3, --COOC.sub.2 H.sub.5, --NHCO--C.sub.1 -C.sub.4 alkyl or --CONH--C.sub.1 -C.sub.4 alkyl, M.sup.+ and M.sub.1.sup.+ are each independently of the other an alkali metal cation, an alkaline earth metal cation or a heavy metal cation or NH.sub.4.sup.+ ; wherein X, Y, X' and Y' are each independently hydrogen, halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5, --NO.sub.2 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, wherein at least two of the cations M.sup.+ and M.sub.1.sup.+ in the compounds forming the mixed crystals of formula I are different and the X-ray diffraction patterns of the mixed crystals differ from the X-ray diffraction patterns of the individual components and of their sum.
    Type: Grant
    Filed: May 8, 1989
    Date of Patent: December 25, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Stefan Hari, Arnold Grubenmann, Andreas Burkhard
  • Patent number: 4978746
    Abstract: A dyestuff of the formula ##STR1## wherein A=H, unsubstituted C.sub.1 -C.sub.4, C.sub.1 -C.sub.4 -alkyl substituted by OH, SO.sub.3 H or COOH or phenyl or COOR',R'=H or C.sub.1 -C.sub.4 -alkyl,X=--CH.dbd.CH.sub.2 or --CH.sub.2 C.sub.2 --Y,Y=--OSO.sub.3 H, --SSO.sub.3 H, --OCOCH.sub.3 or Cl,R=H, unsubstituted C.sub.1 -C.sub.4 -alkyl, or C.sub.1 -C.sub.4 alkyl substituted by OH, SO.sub.3 H, COOH, or OSO.sub.3 H or NR"Z, whereinR".dbd.H, unsubstituted C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkyl substituted by a substituent selected from the group consisting of OH, SO.sub.3 H, COOH, OSO.sub.3 H, and Z=a heterocyclic fiber reactive radical selected from the group consisting of 2,4-dichlorotriazin-6-yl, monohalogeno-sym.-triazinyl, monohalogenopyrimidinyl, dihalogenopyrimidinyl and trihalogenopyrimidinyl. Such dyestuff gives, on cellulose or polypeptide materials, high yields of brilliant yellow dyeings with outstanding wet--and oxidation--fastnesses and a high stability of the fiber--dyestuff bond.
    Type: Grant
    Filed: November 20, 1989
    Date of Patent: December 18, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventor: Karl-Josef Herd
  • 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: 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: 4968783
    Abstract: Reactive dyes useful for dyeing natural and synthetic fibers of the formula ##STR1## in which D.sub.1 is a benzene or naphthalene radical, which can be substituted, D.sub.2 is a benzene radical, which can be substituted, R.sub.1 is hydrogen or C.sub.1-4 -alkyl, the bridge member --N(R.sub.1)-- is bonded to a ring carbon atom of D.sub.2, R.sub.2 is hydrogen or C.sub.1-4 -alkyl, which can be substituted, and R.sub.3 is hydrogen or substituted or unsubstituted alkyl, cycloalkyl, aralkyl or aryl.
    Type: Grant
    Filed: January 19, 1989
    Date of Patent: November 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Karl Seitz, Gert Hegar
  • Patent number: 4968352
    Abstract: Diaryl pigments having excellent dried ink transparency and improved process heat stability are prepared by carrying out the coupling of a bisdiazotized substituted 4,4' diaminobiphenyl with acetoacetanilides and/or pyrazolinones in the presence of an added quantity of one or more substituted aromatic amines containing at least one sulfonic or carboxylic acid substituent, or their salts. The pigments exhibit improved tolerance to variations in drying temperatures and to high drying temperatures, and have improved transparency when present in dried ink formulations.
    Type: Grant
    Filed: April 28, 1988
    Date of Patent: November 6, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Boyd A. Keys, John T. Ouderkirk
  • 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: 4963660
    Abstract: Free radical heavy metal ions in water-soluble heavy metal complex dyestuffs are removed from the synthesis solution of the heavy metal complex dyestuff by means of a compound or several of the compounds mentioned below:(a) saturated and unsaturated fatty acids having about 8 to 18 carbon atoms and water-soluble salts thereof;(b) the monoesters and diesters of orthophosphoric acid and salts thereof corresponding to the general formula (1a) and (1b) ##STR1## in which R denotes a saturated or unsaturated aliphatic radical having about 8 to 18 carbon atoms and M stands for a hydrogen atom or a salt-forming, water-solubilizing metal;(c) aliphatic sulfonic acids and water-soluble salts thereof corresponding to the general formula (2)R--SO.sub.
    Type: Grant
    Filed: August 30, 1988
    Date of Patent: October 16, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Uwe Mrotzeck, Peter Mischke, Gunther Schwaiger, Werner Russ, Manfred Sittig
  • 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: 4960873
    Abstract: Isothiazoleazo dyes I ##STR1## where R.sup.1 is H, halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy and A is the radical of a coupling component are used predominantly as disperse dyes for dyeing hydrophobic organic fibers and fiber materials.
    Type: Grant
    Filed: March 9, 1989
    Date of Patent: October 2, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Guenter Hansen, Gunther Lamm, Helmut Reichelt, Ernst Schefczik
  • Patent number: 4960874
    Abstract: Compounds of the general formula I ##STR1## where R is alkyl or unsubstituted or substituted aryl and K is a radical of the formula ##STR2## B is C.sub.1 -C.sub.4 -alkyl or substituted amino, R.sup.1 is hydrogen, methyl, methoxy or ethoxy, R.sup.2 and R.sup.3 independently of one another are each unsubstituted or substituted alkyl, R.sup.3 may furthermore be hydrogen, R.sup.4 is a radical of the formula --A--OCO--Y--R, Z is hydrogen or methyl, X is hydrogen, methyl, methoxy, chlorine or acylamino, A is C.sub.2 - or C.sub.3 -alkylene and Y is --O-- or --NH--, are very useful for dyeing cellulose esters and synthetic polyesters.
    Type: Grant
    Filed: July 1, 1988
    Date of Patent: October 2, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Udo Bergmann, Johannes D. Dix, Guenter Hansen, Ernst Schefczik, Guenther Seybold
  • Patent number: 4955987
    Abstract: The invention describes a process for the preparation of concentrated aqueous, substantially salt-free solutions of aminotriazinyl reactive dyes, which process comprises starting from a dye which contains sulfo groups and one or more radicals capable of reaction with cyanuric halide, said dye being at least partly in the form of the ammonium salt, reacting said dye with cyanuric halide, in the presence of lithium hydroxide, and deionizing and concentrating the salt-containing synthesis solution by a membrane separation process.The so prepared mixed lithium/ammonium salts of the acid aminotriazinyl reaction dyes are readily water soluble and are suitable for the preparation of concentrated storage stable dye solutions.
    Type: Grant
    Filed: December 6, 1985
    Date of Patent: September 11, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Roger Lacroix, Edmond Ruhlmann
  • Patent number: 4954563
    Abstract: Monoazo dyes of the formula ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, C.sub.2 -C.sub.4 alkanoylamino or is an unsubstituted or substituted arylsulfonyl, aryloxy or arylcarbonyl radical; R.sub.2 is hydrogen, halogen, an unsubstituted or substituted alkyl, aryloxy or aryloxysulfonyl radical or a radical of the formula ##STR2## R.sub.3 is an unsubstituted or substituted alkyl or aryl radical; R.sub.4 is hydrogen or alkyl; and R.sub.5 and R.sub.6 are each independently hydrogen or an unsubstituted or substituted alkyl, cycloalkyl or aryl radical, with the proviso that R.sub.1 may not be hydrogen or halogen if R.sub.2 is an unsubstituted or substituted aryloxysulfonyl radical, a radical of the formula ##STR3## or the trifluoromethyl group, and the sulfo group is attached to the benzene ring of the indole radical, produce dyeings of good light- and wetfastness properties on polyamide material.
    Type: Grant
    Filed: February 27, 1984
    Date of Patent: September 4, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Hurter
  • Patent number: 4952677
    Abstract: Reddish-brown to yellow shade colorants suitable for ribbon and ball point inks are produced from the glassy waste by-product of pararosaniline manufacture by slurrying the residue in mineral acid, diazotizing, and coupling. the resulting colorants are useful in preparing inks.
    Type: Grant
    Filed: September 15, 1988
    Date of Patent: August 28, 1990
    Assignee: BASF Corporation
    Inventors: Floyd G. Spence, Louis R. de Alvare, Robert J. Allen
  • Patent number: 4952680
    Abstract: Stable solutions of azo dyes obtained by diazotizing and coupling m-phenylenediamine or derivatives thereof are prepared after the reaction has ended by treating the resulting reaction mixture with from 0.1 to 1.2 moles of formic acid, based on 1 mole of m-phenylenediamine, at from 60.degree. C. to the boiling point of the reaction mixture.
    Type: Grant
    Filed: April 14, 1988
    Date of Patent: August 28, 1990
    Assignee: BASF Aktiengesellschaft
    Inventor: Karl Schmeidl