Formation Of Azo Group By Coupling Diazonium Compound With Coupling Component In Presence Of Ammonia, A Group Iia Light Metal Hydroxide Or A Group Ia Or Iia Light Metal Phosphate Patents (Class 534/583)
  • Patent number: 7932366
    Abstract: Methods are disclosed for preparing compounds of Formula I: where R1, R3, and R4 are independently hydrogen or C1 to C4 alkyl, and R2 is: where R5 is selected from the group consisting of hydrogen and C1 to C4 alkyl, or where R6, R7 and R8 are independently hydrogen or C1 to C4 alkyl; or the esters or pharmacologically acceptable salts thereof. The methods can involve converting a suitably functionalized aniline compound to a diazonium salt (which aniline compound can be first formed by reduction of a nitrobenzene) and coupling the diazonium salt with a suitably functionalized benzene compound. The suitably functionalized aniline compound either includes a primary alcohol or aldehyde group, which is then oxidized to a carboxylic acid group, or includes a nitrile or amide group, which is hydrolyzed to a carboxylic acid group. The methods can also involve the direct coupling (via reduction of nitro groups to form an azo linkage) of suitably functionalized nitrobenzenes.
    Type: Grant
    Filed: July 7, 2005
    Date of Patent: April 26, 2011
    Assignee: Biocon Limited
    Inventors: Jennifer A. Riggs-Sauthier, Nnochiri N. Ekwuribe
  • Patent number: 5510468
    Abstract: There are described benzophenoneazo dyes of the formula ##STR1## where the ring A can be benzofused and a benzofused ring A can be overbridges,m is 1 or 2,K is the radical of a coupling component,Y is hydrogen or arylazo,one of the two radicals X.sup.1 and X.sup.2 is hydrogen and the other is hydroxysulfonyl,R.sup.1, R.sup.2 and R.sup.3 are independently of the others hydrogen, halogen, C.sub.1 -C.sub.12 -alkyl, cyclohexyl, phenyl, 2-hydroxy-ethylsulfonyl or C.sub.1 -C.sub.4 -alkoxy or, when m is 1 and Y is hydrogen, one of these substituents can also be the radical of the formula ##STR2## where L.sup.1 is a chemical bond or a bridge member, and X.sup.1, X.sup.2, R.sup.4, K and the ring A are each as defined above, andR.sup.4 is hydrogen, halogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: July 27, 1994
    Date of Patent: April 23, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Gunther Lamm, Helmut Reichelt, Ortwin Schaffer
  • Patent number: 5380859
    Abstract: There are described benzophenoneazo dyes of the formula ##STR1## where the ring A can be benzofused and a benzofused ring A can be overbridged,m is 1 or 2,K is the radical of a coupling component,Y is hydrogen or arylazo,one of the two radicals X.sup.1 and X.sup.2 is hydrogen and the other is hydroxysulfonyl,R.sup.1, R.sup.2 and R.sup.3 are independently of the others hydrogen, halogen, C.sub.1 -C.sub.12 -alkyl, cyclohexyl, phenyl, 2-hydroxyethylsulfonyl or C.sub.1 -C.sub.4 -alkoxy or, when m is 1 and Y is hydrogen, one of these substituents can also be the radical of the formula ##STR2## where L.sup.1 is a chemical bond or a bridge member, andX.sup.1, X.sup.2, R.sup.4, K and the ring A are each as defined above, andR.sup.4 is hydrogen, halogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: July 16, 1993
    Date of Patent: January 10, 1995
    Assignee: Basf Aktiengesellschaft
    Inventors: Gunther Lamm, Helmut Beichelt, Ortwin Schaffer
  • Patent number: 5278293
    Abstract: Azo dyestuffs of the formula ##STR1## having the substituent meanings given in the description, are outstandingly suitable for dyeing and printing materials containing hydroxyl groups and amide groups.
    Type: Grant
    Filed: October 31, 1990
    Date of Patent: January 11, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Josef Herd, Manfred Hoppe, Hermann Henk, Klaus Kunde, Frank-Michael Stuohr
  • Patent number: 5270455
    Abstract: A metal complex suitable as dyes for the dyeing of a wide range of textile and non-textile materials, particularly leather and fur, said metal complex of a compound of the formula ##STR1## in which D and D.sub.1, independently of one another, are each the radical of a diazo component of the benzene or naphthalene series and M is a phenylene radical which may be further substituted.
    Type: Grant
    Filed: July 27, 1992
    Date of Patent: December 14, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Ulrich Schlesinger
  • Patent number: 5256194
    Abstract: A recording liquid containing a dye, glycerine, an aliphatic monohydric alcohol and water. The dye is a mixture of C.I. Food Black 2 and at least one compound selected from compounds which are represented by the following general formulas [I] and [II]: ##STR1## [where Q1 is a phenyl group or a naphthyl group which are substituted by a lower alkyl carbonylamino group and a lower alkoxy group or a naphthyl group substituted by a SO.sub.3 M group, Q2 is a naphthyl group substituted by a SO.sub.3 M group or a phenyl group substituted by a lower alkoxy group, Q3 is a phenyl group, a naphthyl group, or a phenyl group or a naphthyl group which are substituted by a SO.sub.3 M group, R.sub.1 and R.sub.2 are each a lower alkyl group, a lower alkoxy group or a lower alkyl carbonylamino group, R.sub.3 is a hydrogen or a phenyl group substituted by a SO.sub.3 M group, n is 0 or 1, and M is an alkaline metal or an ammonium cation.
    Type: Grant
    Filed: September 2, 1992
    Date of Patent: October 26, 1993
    Assignee: Canon Kabushiki Kaisha
    Inventors: Osamu Nishiwaki, Kazuo Iwata, Shinichi Tochihara, Hitoshi Sugimoto
  • Patent number: 5243033
    Abstract: Reactive dyes of the formula ##STR1## in which R.sub.1, R.sub.2 and R.sub.3, independently of one another, are C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, ureido, C.sub.1 -C.sub.4 acylamino, carboxyl and sulfo and n, m and p, independently of one another, are the number 0, 1, 2 or 3, X is fluorine or chorine and Z is an aliphatic, araliphatic, aromatic or heterocyclic amino group free from fibre-reactive radicals; or Z is the radical of an aliphatic or aromatic diamine which contains the radical of the formula ##STR2## in which R.sub.1, R.sub.2, R.sub.3, n, m, p and X are as defined, bound via the second amino group; or Z is a radical of the formula ##STR3## in which R.sub.1, R.sub.2, R.sub.3, n, m, and p are as defined; or Z is a radical --NH--SO.sub.2 --(CH.sub.2).sub.2 --OSO.sub.3 H; and the reactive dye of the formula (1) contains at least two sulfo groups, produce, on cellulose fibres, orange dyeings of high color strength and prints of good fastness properties.
    Type: Grant
    Filed: January 13, 1992
    Date of Patent: September 7, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanassios Tzikas
  • Patent number: 5239063
    Abstract: Fiber reactive azo dyestuffs of the formula ##STR1## in which R=H or C.sub.1 -C.sub.6 alkyl, which can be substituted with OH, Hal, SO.sub.3 H or OSO.sub.3 H;Z=heterocyclic five or six membered ring;n, m=0, 1 or 2, wherein n+m=0, 1 or 2;Y=OH, OR, NR.sub.2 R.sub.3, OMe; andR.sub.2, R.sub.3, =H, R and R.sub.2, R.sub.3 and N can form a heterocyclic 5 or 6-membered ring.
    Type: Grant
    Filed: January 9, 1992
    Date of Patent: August 24, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Hoppe, Martin Michna, Karl-Josef Herd, Frank-Michael Stohr
  • 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: 5175260
    Abstract: Disazo dyes suitable for preparing inks have the formula ##STR1## where m is 1 or 2,n is 0 or 1,Z.sup.1 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl,Z.sup.2 is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkanoyl, substituted or unsubstituted benzoyl, C.sub.1 -C.sub.4 -alkylsulfonyl, substituted or unsubstituted phenylsulfonyl or a derivatized 1,3,5-triazinyl radical, andD is the radical of a diazo component of the class of the thiazole, thiophene, aminobenzoic acid or phenylenediamine compounds.
    Type: Grant
    Filed: August 8, 1991
    Date of Patent: December 29, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Gunter-Rudolf Schroeder, Udo Mayer
  • 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: 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: 5075428
    Abstract: A dyestuff of the formula ##STR1## in which R is H or Ch.sub.3 ##STR2## in which R.sub.1 is H, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or --X--YX is a divalent aliphatic, cycloaliphatic, aliphaticcycloaliphatic radical or an araliphatic radicalY is COOH, SO.sub.3 H, OSO.sub.3 H or SO.sub.2 G, in whichG is CH.dbd.CH.sub.2 or --CH.sub.2 --CH.sub.2 --Z, in which Z denotes a group which can be eliminated under alkaline conditions,R.sub.2 is H or C.sub.1 -C.sub.4 -alkyl, and the benzene radical D and the benzene or naphthalene radical L can contain customary substituents,is suitable for the dyeing and printing of OH- and NH-containing materials. They produce lightfast and wetfast brilliant dyeings and prints.
    Type: Grant
    Filed: July 11, 1989
    Date of Patent: December 24, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventor: Horst Jager
  • Patent number: 5069719
    Abstract: Disclosed is an organic solvent based ink composition which contains a specific dye and an organic solvent, especially an alcohol or a glycol and which has excellent stability with time and good writing properties. The organic solvent based ink composition comprises a dye and an organic solvent, wherein the dye is represented by ##STR1## wherein D represents a residue of an azo or anthraquinone dye which does not have a sulfone group and a carboxyl group, X represents an oxygen atom or a methylene group, Y represents a C.sub.2 -C.sub.12 alkyl group, a C.sub.2 -C.sub.4 hydroxyalkyl group, a C.sub.2 -C.sub.12 alkoxyalkyl group, a polybutyral residue, a polyvinyl alcohol residue, a phenol resin residue, or a cellulose residue and m shows 0 or 1.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: December 3, 1991
    Assignee: Orient Chemical Industries, Ltd.
    Inventor: Takashi Ono
  • 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: 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: 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: 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: 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: 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: 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: 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: 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: 4994563
    Abstract: The azo dyes of the formula ##STR1## in which D is a diazo component, R.sub.1 and R.sub.2 independently of one another are each a C.sub.1 -C.sub.10 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or naphthyl radical each of which is substituted or unsubstituted, or R.sub.1 and R.sub.2, together with the nitrogen atom linking them, are a 5-membered, 6-membered or 7-membered ring each of which is unsubstituted or substituted by heteroatoms, R.sub.3 is hydrogen, halogen or a C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxy or phenoxy radical each of which is substituted or unsubstituted, X is --CO-- or --SO.sub.2 --, n is the number 1, 2, 3, 4, 5 or 6 and M is a cation, produce dyeings of good fastness properties on fibre materials containing nitrogen or containing hydroxyl groups. This application also relates to the preparation and use of said azo dyes and to intermediates utilized in the preparation of said azo dyes.
    Type: Grant
    Filed: June 27, 1989
    Date of Patent: February 19, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Harald Walter, Rudolf Hurter
  • 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: 4994111
    Abstract: The dye of the formula: ##STR1## which is suitable for use in aqueous inks, especially for ink jet printing.
    Type: Grant
    Filed: November 30, 1989
    Date of Patent: February 19, 1991
    Assignee: Canon Kabushiki Kaisha
    Inventors: Arthur Quayle, Cecil V. Stead
  • 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: 4973671
    Abstract: Double copper formazan reactive dyes of the formula ##STR1## in which R.sup.1 is hydrogen, hydroxylsulfonyl or chlorine; R.sup.2 is hydrogen or hydroxylsulfonyl; one of two radicals R.sup.3 and R.sup.4 is hydrogen and the other is hydroxylsulfonyl; Q is fluorine or chlorine; and X is a radical of the formula ##STR2## where R.sup.5 and R.sup.6 are identical or different and each is independently of the other hydrogen or unsubstituted or cyano- or hydroxyl-substituted C.sub.1 -C.sub.4 -alkyl and Y is hydroxyl or the radical NR.sup.7 R.sup.8 where R.sup.7 and R.sup.8 are identical or different and each is independently of the other hydrogen or unsubstituted or cyano-, hydroxyl- or hydroxylsulfonyl-substituted C.sub.1 -C.sub.4 -alkyl, with the proviso that R.sup.5 and R.sup.6 are not both hydrogen, or salts thereof are useful for dyeing and printing hydroxyl- or nitrogen-containing organic substrates.
    Type: Grant
    Filed: November 4, 1988
    Date of Patent: November 27, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Pandl, Manfred Patsch
  • 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: 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: 4933436
    Abstract: Azo dyes are obtained by diazotizing an aromatic amine and combining the resulting diazonium salt solution with a sulpho-containing coupling component when the sole acid donor used for the diazotization reaction--instead of the otherwise customary mineral or fatty acids--is a low molecular weight, nonsurfactantlike aromatic sulphonic acid.
    Type: Grant
    Filed: January 27, 1987
    Date of Patent: June 12, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Joachim Wolff, Karl-Heinz Wolf, Reinhold M. Klipper
  • Patent number: 4931550
    Abstract: The dye of the formula: ##STR1## which is suitable for use in aqueous inks, especially for ink jet printing.
    Type: Grant
    Filed: May 5, 1987
    Date of Patent: June 5, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventors: Arthur Quayle, Cecil V. Stead
  • Patent number: 4920205
    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/netural pH-ranges. More specifically, an aqueous/alkaline solution of the coupling component is continuously mixed in a first reaction step with an aqueous solution of acetic acid, boric acid, phosphoric acid, hydrochloric acid or sulfuric acid at a temperature lower than 65.degree. C. within a period of less than 1 minute, during which the coupling component commenences precipitating at least partially as reactive matter; next, the suspension obtained is continuously mixed, in a second reaction step immediately following the first reaction step, with an aqueous/acid solution of the diazo component at a temperature of less than 65.degree. C.
    Type: Grant
    Filed: March 28, 1989
    Date of Patent: April 24, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heinrich Rehberg, Hartmut Behringer
  • 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
  • Patent number: 4917731
    Abstract: Water-soluble black trisazo dyestuffs of the general formula I ##STR1## wherein R denotes hydrogen, alkyl having 1 or 2 carbon atoms, alkoxy having 1 or 2 carbon atoms, acylamino having 2 or 3 carbon atoms or carboxamide and n denotes a number from 0 to 2.5 are suitable for the preparation of recording fluids.
    Type: Grant
    Filed: December 12, 1988
    Date of Patent: April 17, 1990
    Inventors: Wolfgang Bauer, Konstantin Morgenroth, Kuno Reh, Josef Ritter
  • Patent number: 4910298
    Abstract: A monoazo compound of the following formula, ##STR1## wherein D is sulfonaphthyl, sulfophenyl or carboxyphenyl, any one of A.sub.1 and A.sub.2 is sulfo and the other is hydrogen, methoxy or ethoxy, R.sub.1 and R.sub.2 are independently hydrogen or alkyl, B.sub.1 and B.sub.2 are independently phenylene or naphthylene, and Y.sub.1 and Y.sub.2 are independently vinyl, .beta.-sulfatoethyl or the like, which is useful for dyeing or printing fiber materials to give dyed or printed products of a deep color excellent in fastness properties.
    Type: Grant
    Filed: November 3, 1987
    Date of Patent: March 20, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazufumi Yokogawa, Sadanobu Kikkawa, Naoki Harada, Takashi Omura
  • Patent number: 4906739
    Abstract: A fibre-reactive azo dyestuff of the formula ##STR1## in which X is alkyl or alkoxy with 1 to 4 carbon atoms, carboxyl or halogen, n is 1, 2 or 3, m is 0 or 1, p is 0 or 1 and q is 0 or 1 and the benzene or naphthalene rings A, B and B' can contain further substituents in addition to SO.sub.3 H groups. The dyestuffs of the invention are suitable inter alia, for dyeing and printing silk, leather, wool, high molecular weight polyamide fibres and high molecular weight polyurethanes, but especially cellulose-containing materials having a fibrous structure.
    Type: Grant
    Filed: June 15, 1989
    Date of Patent: March 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Herbert Seiler, Gert Hegar
  • Patent number: 4894447
    Abstract: Azo dyes of the formula ##STR1## or tautomeric forms thereof, in which: Z is N or CH,X is O, NR.sub.1 or N,W is N or C,K is a coupling component,R is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, nitro, --CN, --NHR.sub.1, --NH-acyl, phenoxy, --COOH, COOR.sub.1, --CONHR.sub.1 or substituted or unsubstituted phenyl, R.sub.1 being hydrogen, substituted or unsubstituted C.sub.1 -C.sub.6 -alkyl or substituted or unsubstituted phenyl,M is H.sup..sym., Li.sup..sym., Na.sup..sym., K.sup..sym., NH.sub.4.sup..sym. or the protonated form of a C.sub.4 -C.sub.12 -trialkylamine, of a C.sub.4 -C.sub.12 -diamine or of a C.sub.2 -C.sub.12 -alkanolamine,A is a carbocyclic or nitrogen-containing aromatic radical which can be further substituted, andB is a 1,4-phenylene radical which can be further substituted.
    Type: Grant
    Filed: April 9, 1987
    Date of Patent: January 16, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Jean-Marie Adam
  • Patent number: 4891424
    Abstract: 4-Aralkyl-2-nitro-2'-hydroxy-3',5'-dialkyl (or cumyl)-azobenzenes are made by coupling the corresponding diazotized 4-aralkyl-o-nitroaniline with the corresponding phenol. These azobenzene intermediates are used to prepare the corresponding 2H-benzotriazole UV absorber stabilizers substituted on the 5-position of the benzo ring by an aralkyl group, preferably alpha,alpha-dimethylbenzyl.
    Type: Grant
    Filed: April 1, 1988
    Date of Patent: January 2, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Raymond Seltzer, Roland A. E. Winter
  • Patent number: 4889924
    Abstract: A bisazo compound having good electrophotographic properties is disclosed, which is represented by formula (I) ##STR1## wherein X represents a hydrogen atom, a chlorine atom or a nitro group. A process for producing the bisazo compound is also disclosed.
    Type: Grant
    Filed: October 2, 1987
    Date of Patent: December 26, 1989
    Assignee: Fuji Xerox Co., Ltd.
    Inventors: Yutaka Akasaki, Akihiko Tokita, Kaoru Torikoshi, Akira Imai, Touru Ishii
  • Patent number: 4881977
    Abstract: Water-soluble, yellow monoazo dyestuffs of the formula ##STR1## wherein R.sup.1 is a moiety of the formula ##STR2## R.sup.2 is methyl, ethyl, methoxy or ethoxy, R.sup.3 is methyl or ethyl, andn is a number from 0.3 to 1.7,are useful for the preparation of recording fluids.
    Type: Grant
    Filed: September 19, 1988
    Date of Patent: November 21, 1989
    Assignee: Cassella Aktiengesellschaft
    Inventors: Wolfgang Bauer, Willi Steckelberg, Josef Ritter
  • Patent number: 4866163
    Abstract: Compounds of the formula ##STR1## wherein each R.sub.1 is independently hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or --NHCOC.sub.1-4 alkyl, each R.sub.2 is H, halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, each R.sub.3 is independently halo, hydroxy, C.sub.1-4 alkoxy, --NHOH, amino or an aliphatic, aromatic cycloaliphatic or saturated heterocyclic amino radical, and is divalent aliphatic or aromatic group or, together with the NH radicals to which it is attached, forms a piperazine ring, and the use thereof for dyeing or printing hydroxy group- or nitrogen-containing organic substrates after which the dyed or printed substrate is optionally treated with a cationic fixing agent.
    Type: Grant
    Filed: May 2, 1984
    Date of Patent: September 12, 1989
    Assignee: Sandoz, Ltd.
    Inventor: Werner Koch
  • Patent number: 4853466
    Abstract: This invention relates to disazo dyes, and their metal complexes, which are useful for dyeing cellulosic fibers in lightfast and washfast hues. In addition, these dyes have high water solubility, a high degree of fixation, acceptable migration and high water solubility with reasonable cost.The disazo dyes have the structure: ##STR1## Wherein: R is selected from ##STR2## Wherein the azo bonds are ortho to the --OH or NH.sub.2 groups;R.sub.1 is H, lower alkyl, lower alkoxy, or --CO.sub.2 M;R.sub.2 is H, lower alkyl, lower alkoxy, Cl;R.sub.3 is lower alkylene;R.sub.4 is H, --lower alkyl;R.sub.5 is H, lower alkyl, --CO.sub.2 M;R.sub.6 is OH or --NH.sub.2 ;R.sub.7 is H, --CH.sub.2 SO.sub.3 M;M is H, Na, Li, K, Mg, Ca, NH.sub.4 ; ##STR3## and n is 0, 1, 2.
    Type: Grant
    Filed: November 20, 1987
    Date of Patent: August 1, 1989
    Assignee: Crompton & Knowles Corporation
    Inventor: James F. Feeman
  • Patent number: 4851516
    Abstract: This invention relates to novel disazo dyes and processes for their production having the structure: ##STR1## wherein: R.sub.1 is H, lower alkyl, chloro, lower alkoxy, --CO.sub.2 M;R.sub.2 is H, lower alkyl, lower alkoxy, chloro;R.sub.3 is lower alkylene;R.sub.4 is H or lower alkyl;R.sub.5 is H, lower alkyl, lower alkoxy, chloro, nitro, --NHCO-- lower alkyl; CF.sub.3 ;R.sub.6 is H, lower alkyl, lower alkoxy, chloro, --SO.sub.3 M;R.sub.7 is --SO.sub.3 M, --CO.sub.2 MM is H, Na, Li, K, N.sub.
    Type: Grant
    Filed: November 20, 1987
    Date of Patent: July 25, 1989
    Assignee: Crompton & Knowles Corporation
    Inventor: James F. Feeman
  • Patent number: 4841037
    Abstract: A naphthalene trisazo compound represented by the general formula (I) or (II): ##STR1## wherein A and B each represents a substituted or unsubstituted benzene or naphthalene ring; m represents zero or 1; and M represents an alkali metal atom, ammonium or H.Am (wherein Am represents an amine); or ##STR2## wherein X represents a hydrogen atom, a lower alkyl group, a phenyl group or a phenyl group substituted by --SO.sub.3 M; m represents zero or 1; M represents an alkali metal atom, ammonium or H.Am (wherein Am represents an amine); A, B and C each represents a substituted or an unsubstituted benzene or naphthalene ring, provided that B and C do not represent a naphthalene ring at the same time. A recording liquid containing these compounds is suitable for use in an ink-jet recording system.
    Type: Grant
    Filed: June 10, 1986
    Date of Patent: June 20, 1989
    Assignees: Canon Kabushiki Kaisha, Mitsubishi Chemical Industries Limited
    Inventors: Tokuya Ohta, Masatsune Kobayashi, Yuko Suga, Konoe Miura, Hiroshi Takimoto, Tomio Yoneyama
  • Patent number: 4833235
    Abstract: Disazo compounds of the formula ##STR1## and salt thereof, D is the radical of a diazo component of the benzene or naphthalene series.K is the radical of a heterocyclic coupling component of the aminopyrazole-, pyridone- or barbituric acid-series, n is 1 to 4,R.sub.1 is hydrogen, C.sub.1-4 alkyl or substituted C.sub.1-4 alkyl,each of R.sub.2 and R.sub.3 is independently hydrogen, halo, C.sub.1-4 alkyl, substituted C.sub.1-4 alkyl, C.sub.1-4 alkoxy, substituted C.sub.1-4 alkoxy, --NHCO--Rhd 5, amino, substituted amino or a quaternary ammonium group, wherein R.sub.5 is C.sub.1-4 alkyl, substituted C.sub.1-4 alkyl, C.sub.1-4 alkoxy or amino,R.sub.4 is hydrogen, C.sub.1-4 alkyl, C.sub.
    Type: Grant
    Filed: October 7, 1987
    Date of Patent: May 23, 1989
    Assignee: Sandoz Ltd.
    Inventor: Reinhard Pedrazzi
  • Patent number: 4795807
    Abstract: Azo disperse dyestuffs are prepared by diazotization and coupling in an aqueous phase, the coupling being carried out in the presence of an ester of a lower aliphatic carboxylic acid.
    Type: Grant
    Filed: March 30, 1987
    Date of Patent: January 3, 1989
    Assignee: Cassella Aktiengesellschaft
    Inventors: Ulrich Buhler, Friedrich Schophoff, Wolf Weidemuller
  • Patent number: 4771129
    Abstract: An azo compound of the formula: ##STR1## wherein M.sub.1, M.sub.2 and M.sub.3 are, the same or different, each a hydrogen atom, an alkali metal atom, an ammonium group or an organic ammonium group; R.sub.1 and R.sub.2 are, the same or different, each a C.sub.1 -C.sub.3 alkyl group, a C.sub.1 -C.sub.3 alkoxy group, a halogen atom or a hydrogen atom; m is 1 or 2; and X and Y are, the same or different, each a C.sub.6 -C.sub.18 alkylamine, alkoxyalkylamine, arylamine, aralkylamine, alkanolamine or alkarylamine residue, which is useful as a magenta color dyestuff for an aqueous ink composition, particularly for ink jet recording.
    Type: Grant
    Filed: March 13, 1986
    Date of Patent: September 13, 1988
    Assignees: Taoka Chemical Company, Limited, Sumitomo Chemical Company, Limited
    Inventors: Hideo Kawashita, Mitsuhiro Ota