Formation Of Azo Group By Coupling Diazonium Compound With Coupling Component In Presence Of An Additional Organic Compound Patents (Class 534/581)
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Patent number: 5597905Abstract: Described is a process for preparing benzothiazolylazoanilines by diazotization of 2-aminobenzothiazoles in a mixture consisting essentially of phosphoric acid, sulfuric acid and water using customary diazotizing agents and subsequent addition of the reaction mixture to an aqueous acidic solution of the anilines.Type: GrantFiled: December 15, 1995Date of Patent: January 28, 1997Assignee: BASF AktiengesellschaftInventor: Rudolf Bermes
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Patent number: 5578711Abstract: Dyestuffs of the formula ##STR1## in which D is the radical of an aromatic or heterocyclic diazo component andK is the radical of an aromatic or heterocyclic coupling component, or is the radical of an active methylene compound,are obtained in an ecologically advantageous manner by reacting an aromatic or heterocyclic diazo components of the formulaD--NH.sub.2and a coupling component of the formulaH--Kwith a nitrite, for example NaNO.sub.2, in the presence of CO.sub.2 at a pressure of 5-100 at. The process is suitable in particular for the preparation of concentrated dye-stuff solutions, because expensive operations, such as, for example, pressure permeation and reverse osmosis, can be omitted.Type: GrantFiled: September 14, 1995Date of Patent: November 26, 1996Assignee: Bayer AktiengesellschaftInventors: Roderich Raue, Alfred Brack, Karl-Heinrich Lange
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Patent number: 5541299Abstract: Dyestuffs of the formula ##STR1## in which D is the radical of an aromatic or heterocyclic diazo component andK is the radical of an aromatic or heterocyclic coupling component, or is the radical of an active methylene compound,are obtained in an ecologically advantageous manner by reacting an aromatic or heterocyclic diazo components of the formulaD--NH.sub.2and a coupling component of the formulaH--Kwith a nitrite, for example NaNO.sub.2, in the presence of CO.sub.2 at a pressure of 5-100 at. The process is suitable in particular for the preparation of concentrated dye-stuff solutions, because expensive operations, such as, for example, pressure permeation and reverse osmosis, can be omitted.Type: GrantFiled: September 23, 1994Date of Patent: July 30, 1996Assignee: Bayer AktiengesellschaftInventors: Roderich Raue, Alfred Brack, Karl-Heinrich Lange
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Patent number: 5532344Abstract: A process for producing a monoazodye of the following formula (III): ##STR1## wherein X.sup.1 is nitro or halogen, X.sup.2 is halogen, R.sup.1 is lower alkoxy, R.sup.2 is lower alkyl, each of R.sup.3 and R.sup.4, which are independent of each other, is alkyl, cyanoalkyl or alkylcarbonyloxyalkyl, and each of m and n, which are independent of each other, is 0 or 1, which comprises diazotizing an aniline derivative of the following formula (I): ##STR2## wherein X.sup.1 and X.sup.2 are as defined above, followed by coupling with an aniline derivative of the following formula (II): ##STR3## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, m and n are as defined above, wherein a reaction mixture obtained by the coupling reaction is heat-treated in the presence of a polyoxyethylene higher fatty acid ester type nonionic surfactant, followed by filtration to obtain said monoazo compound in the form of a cake.Type: GrantFiled: March 29, 1993Date of Patent: July 2, 1996Assignee: Dystar Japan Ltd.Inventors: Kiyoshi Himeno, Toshio Hihara, Yoshiharu Hamano, Shinji Kubo
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Patent number: 5508389Abstract: If highly concentrated aqueous solutions of azo dyes are prepared directly by diazotization and coupling reactions, appreciable difficulties generally result as a consequence of the fact that the diazotization and coupling reactions give rise to viscous phases which lead to stirring problems in the reaction apparatus used, which in turn results in an incomplete synthesis. The novel process for preparing concentrated aqueous dye solutions of an anionic dye in an aqueous medium overcomes this disadvantage by carrying out the diazotization of the aromatic amine diazo component and/or the coupling reaction between the diazonium salt and the coupling component in the presence of an auxiliary which exerts a viscosity-reducing effect on pasty phases. Examples of such auxiliaries are optionally alkyl-substituted naphthalenesulfonic acid-formaldehyde condensation products, ligninsulfonates, polyacrylates and copolymers of maleic anhydride and methacrylic acid or acrylic acid.Type: GrantFiled: March 26, 1993Date of Patent: April 16, 1996Assignee: Hoechst AktiengesellschaftInventors: Peter Mischke, Kurt Hohmann, Eckhard Schwab, Manfred Sittig
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Patent number: 5502173Abstract: 2,4,6-trifluoro-5-chloro-pyrimidine and the aqueous solution of a salt of 2-amino-5-aminomethyl-naphthalene-1-sulphonic acid are simultaneously metered into a reactor in approximately equimolar amounts and afford a valuable intermediate for the preparation of high-purity dyes.Type: GrantFiled: September 27, 1994Date of Patent: March 26, 1996Assignee: Bayer AktiengesellschaftInventors: Horst Ja/ ger, Siegbert Arnold, Richard Sommer
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Patent number: 5502171Abstract: Dyestuffs of the formula ##STR1## in which D is the radical of an aromatic or heterocyclic diazo component andZ is the radical of an aromatic or heterocyclic coupling component,are obtained in an ecologically advantageous manner by reacting an aromatic or heterocyclic diazo components of the formulaD--NH.sub.2and a coupling component of the formulaH--Z.sub.1with a nitrite, in the presence of CO.sub.2 at a pressure of 5-100 at. The process is suitable in particular for the preparation of concentrated dyestuff solutions, because expensive operations, such as, for example, pressure permeation and reverse osmosis, can be omitted.Type: GrantFiled: May 16, 1995Date of Patent: March 26, 1996Assignee: Bayer AktiengesellschaftInventors: Roderich Raue, Alfred Brack, Karl-Heinrich Lange
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Patent number: 5493011Abstract: Water-insoluble azo colorants, their preparation and use The invention relates to monoazo and disazo compounds of the formula (I) ##STR1## in which D is the radical of a carbocyclic or heterocyclic diazo or bisdiazo component, R.sup.1 and R.sup.2, independently of one another, are each a substituted or unsubstituted aryl or heteroaryl radical, X.sup.1 and X.sup.2, independently of one another, are each ring-forming ether oxygen or a substituted or unsubstituted imide grouping and n has the value 0 or 1, in which rings A and B, independently of one another, can each be additionally substituted and/or carry substituted or unsubstituted fused rings.These new compounds of the formula (I) are obtained by coupling diazotized amines or diamines of the type D--NH.sub.2 or H.sub.2 N--D--NH.sub.2 with (benzoxazol-2-yl)- or (benzimidazol-2-yl)-arylacetamides.Depending on the presence and length of alkyl chains, the compounds of the formula (I) are suitable for use as pigments, disperse dyes or oil-soluble dyes.Type: GrantFiled: November 6, 1992Date of Patent: February 20, 1996Assignee: Hoechst AGInventors: Rudiger Jung, Reinhold Deubel
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Patent number: 5484900Abstract: 1:2 chromium complex dyestuffs of the formula (I) ##STR1## in which A, B, R.sup.1, R.sup.2, R.sup.3, R.sup.4, p, m, n, n' and Cat.sup.(+) have the meaning given in the description, are suitable for dyeing and printing amido-containing materials.Type: GrantFiled: February 25, 1994Date of Patent: January 16, 1996Assignee: Bayer AktiengesellschaftInventor: Winfried Mennicke
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Patent number: 5459245Abstract: Reactive dyestuffs which, in the form of the free acid, have the following formula ##STR1## in which the substituents have the meaning given in the description, are suitable for the dyeing and printing of hydroxyl- and amido-containing materials, in particular cellulose materials.Type: GrantFiled: October 27, 1994Date of Patent: October 17, 1995Assignee: Bayer AktiengesellschaftInventor: Horst Jaeger
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Patent number: 5446135Abstract: Dyes having the specific structural formula (1) set out below, their copper salt dyes, water-soluble azo dyes containing the dyes or the copper salt dyes, and polarizing films containing the water-soluble azo dyes: ##STR1## wherein A means a benzene or naphthalene ring having a sulfone group or a base thereof, Y and Z individually denote a group of the following formula (a); ##STR2## wherein R.sup.2 is a hydrogen atom, a methyl group, a methoxyl group or an ethoxyl group and R.sup.3 is a methyl, methoxyl or ethoxyl group,R.sup.1 represents an amino, C.sub.1-4 alkylamino, C.sub.2-4 alkylcarboxyamino, benzoylamino or phenylamino group bonded to the 6 or 7 position of the naphthalene ring, and X denotes a hydrogen, sodium, potassium or lithium atom, with the proviso that Y and Z are different but, when both R.sup.2 s are hydrogen atoms and both R.sup.3 s are methoxyl groups, Y and Z may be the same.Type: GrantFiled: March 14, 1994Date of Patent: August 29, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tsutami Misawa, Akira Ogiso, Rihoko Imai, Hisato Itoh
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Patent number: 5436322Abstract: A process for the preparation of compounds of the formula I is described ##STR1## in which R.sup.1 and R.sup.2 independently of one another are C.sub.1 -C.sub.7 alkyl; and R.sup.3 is hydrogen or halogen, by reaction of a diazonium salt of a 2-nitroaniline in acid aqueous solution with a phenol dispersed in water.The process comprises employing as the dispersant a C.sub.8 -C.sub.20 alkanesulfonic acid or a corresponding alkanesulfonate or a mixture of sulfonic acid and sulfonate together with a polyvinyl alcohol.The resulting compounds of the formula I can advantageously be reacted further to give benzotriazoles of the formula V ##STR2## which are used as light stabilizers.Type: GrantFiled: September 12, 1994Date of Patent: July 25, 1995Assignee: Ciba-Geigy CorporationInventors: Ivan Orban, Martin Holer
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Patent number: 5428136Abstract: Disazo compounds of the formula (I) ##STR1## in which R.sup.1 and R.sup.2 are identical or different and are a hydrogen or halogen atom or a C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.5 -alkoxycarbonyl, nitro, cyano or trifluoromethyl group and the rings A, B, C and D independently of one another are unsubstituted or contain one or more substituents from the group comprising C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, carboxyl, C.sub.1 -C.sub.5 -carbalkoxy, C.sub.2 -C.sub.5 -alkanoyl, benzoyl, acyloxy, acylamino, unsubstituted or N-mono- or N,N-disubstituted carbamoyl or unsubstituted or N-mono- or N,N-disubstituted sulfamoyl, possible substituents being C.sub.1 -C.sub.4 -alkyl or mono- to trisubstituted phenyl; C.sub.1 -C.sub.4 -alkylamino or phenylamino; C.sub.1 -C.sub.Type: GrantFiled: July 29, 1993Date of Patent: June 27, 1995Assignee: Hoechst AGInventors: Rudiger Jung, Joachim Weide, Hans J. Metz
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Patent number: 5354850Abstract: Water-soluble disazo compounds, a process for their preparation and their use as dyes.Disazo compounds are described which have the formula (1) given and defined below and are used in their function as fiber-reactive dyes for the dyeing of hydroxy- and/or carboxamido-containing fiber material, such as cellulose fiber materials and synthetic and natural polyamide fiber materials, such as wool. They produce brown dyeings and prints having high color strength and good color fastness by the application and fixation methods customary for fiber-reactive dyes ##STR1## in which R is hydrogen or sulfo,R.sup.1 is hydroxy, methoxy or ethoxy,is hydrogen or an alkali metal and the non-fixed sulfo group in the naphthylene radical is in the 6 or 7 position.Type: GrantFiled: June 24, 1993Date of Patent: October 11, 1994Assignee: Hoechst AGInventors: Andreas von der Eltz, Werner H. Russ
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Patent number: 5258505Abstract: Disclosed herein is an azo compound represented by the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 each are a group or atom selected from the group consisting of a hydrogen atom, alkyl groups having 1 to 4 carbon atoms, a methoxy group, halogen atoms, COOM and COOR.sub.4 in which R.sub.4 is an alkyl group having 1 to 4 carbon atoms, and M denotes an alkali metal atom, or an ammonium or organic ammonium ion. An ink containing this compound is suitable for use in an ink-jet recording.Type: GrantFiled: March 27, 1992Date of Patent: November 2, 1993Assignee: Canon Kabushiki KaishaInventors: Tsuyoshi Eida, Mayumi Yamamoto, Takao Yamamoto
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Patent number: 5247071Abstract: Acetalized azo dyes are prepared by diazotizing an amine, coupling with a hydroxyalkyl-containing coupling component and subsequently reacting with a vinyl ether in a process which comprises carrying out the coupling reaction in a two-phase reaction mixture comprising water and an aromatic hydrocarbon, subsequently separating off the aqueous phase and reacting the azo dye, which is present in the organic phase, without intermediate isolation, with a vinyl ether in the presence of a polybasic carboxylic acid as catalyst.Type: GrantFiled: June 5, 1992Date of Patent: September 21, 1993Assignee: BASF AktiengesellschaftInventors: Guenter Hansen, Georg Zeidler
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Patent number: 5243031Abstract: A process for the production of a monoazo lake coated with a water-insoluble metal salt of rosin, which comprises the steps of:(a) adjusting a mixed solution containing a monoazo dye having a water-soluble group and an alkali metal or ammonium salt of rosin to pH of 8 to 12, and adding an stoichiometeric amount of a metal salt of at least one metal for insolubilizing rosin selected from the group consisting of zinc, aluminum, copper and manganese to form a water-insoluble rosin metal salt, and(b) adjusting the resultant mixture containing the water-insoluble rosin metal salt to pH of 9 to 12 and adding a metal salt of at least one metal for forming a lake of a monoazo dye selected from the group consisting of calcium, barium and strontium to form a monoazo lake.Type: GrantFiled: January 6, 1992Date of Patent: September 7, 1993Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Hitoshi Sugamo, Nobuyuki Tomiya, Yusuke Watabe
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Patent number: 5243032Abstract: The production which is customary in practice of monoazo compounds based on dichloro- and trichloroanilines or disazo compounds of the chlorinated biphenyl series by conventional coupling methods meets with difficulties in that the resulting pigments are contaminated by traces of polychlorinated biphenyls.According to the invention, it has now been found that by addition of water-soluble olefins of the type ##STR1## (R =H, alk or Oalk; X =--COOR.sup.1, --CONHR.sup.2 or --NR.sup.3 COR.sup.4)in the azo coupling, the side reactions which form PCBs can be decidedly suppressed during synthesis of the pigments.Type: GrantFiled: February 21, 1992Date of Patent: September 7, 1993Assignee: Hoechst AktiengesellschaftInventor: Wolfgang Rieper
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Patent number: 5241058Abstract: Azo dye salts corresponding to formula I are suitable as masking couplers. ##STR1## In Formula I, A denotes an optionally substituted aryl group;CC denotes a group optionally carrying a ballast group and capable of coupling under the conditions of photographic color development to produce a dye preferably a cyan dye (color coupler residue);L denotes a linking member which is attached at the coupling position of the color coupler residue by an oxygen, sulphur or nitrogen atom;Z denotes a group conferring solubility in alkalies;R denotes NH--CO--R.sup.1, NH--SO.sub.2 --R.sup.1, COOR.sup.2 or NR.sup.1 --R.sup.2 ;R.sup.1 denotes an optionally substituted alkyl or aryl group;R.sup.2 denotes H or a group such as R.sup.1 ;[M.sup..sym. ] denotes a mixture of organic and inorganic cations optionally containing protons, in which the proportion of organic cation amounts to at least 1/2 mol per mol of dye;m stands for 0, 1 or 2; andn stands for 1, 2, 3 or 4; n.gtoreq.m.Type: GrantFiled: May 15, 1991Date of Patent: August 31, 1993Assignee: Agfa-Gevaert AktiengesellschaftInventors: Gunter Renner, Hans Langen, Ulrich Klein
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Patent number: 5216139Abstract: Thiopheneazo dyes of the formula ##STR1## where R.sup.1 is cyano, C.sub.1 -C.sub.4 -alkoxycarbonyl, phenylazo, phenylsulfonyl, formyl or the radical ##STR2## where R.sup.7 and R.sup.8 are independently of the other cyano or C.sub.1 -C.sub.4 -alkoxycarbonyl,R.sup.2 is C.sub.1 -C.sub.4 -alkyl, phenyl, halogen, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkoxycarbonyl, or R.sup.1 and R.sup.2 together are the radical (CH.sub.2).sub.3 --CO, which may be substituted by 1 or 2 methyl groups and whose carbonyl group is bonded to the thiophene ring in the ortho position relative to the sulfur atom,R.sup.3 is cyano or C.sub.1 -C.sub.4 -alkoxycarbonyl,R.sup.4 is C.sub.1 -C.sub.8 -alkyl, cyclohexyl, phenoxy-C.sub.1 -C.sub.4 -alkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted thienyl,R.sup.5 is C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.7 -alkyl whose alkyl chain is interrupted by 1 or 2 oxygen atoms, or C.sub.1 -C.sub.4 -alkoxy andR.sup.6 is cyanoethyl, phenylethyl or C.sub.3 -C.sub.Type: GrantFiled: December 4, 1990Date of Patent: June 1, 1993Assignee: BASF AktiengesellschaftInventors: Karl-Heinz Etzbach, Guenter Hansen, Gunther Lamm, Helmut Reichelt
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Patent number: 5204453Abstract: The invention relates to a process for the preparation of 1:2 chromium, 1:2 cobalt, 1:2 nickel or 1:2 iron complex azo dyes diazotisation, coupling and metallizing, without isolation of the coupling product, which process comprises diazotizing at least one amine of the benzene or naphthalene series in aqueous solution and coupling the diazonium compound so obtained to at least one coupling component of the benzene or naphthalene series or of the heterocyclic series, such that the azo dye obtained as intermediate contains groups suitable for metal complex formation, and carrying out the diazotization or coupling in the presence of a chromium, cobalt, nickel or iron donor.The dyes obtained by the process of the invention are suitable for dyeing in particular wool or synthetic textile polyamide fibre materials as well as leather, and for use as wood mordant dyes.Type: GrantFiled: December 30, 1991Date of Patent: April 20, 1993Assignee: Ciba-Geigy CorporationInventors: Bernard Chambon, Horst H. Jager, Rudiger Oxenius, Alois Puntener
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Patent number: 5200511Abstract: Reactive dyes of the formula ##STR1## where m is 0 or 1,A.sup.1 and A.sup.2 are different and each is a fiber-reactive radical or else, in the case of A.sup.2, hydrogen,D.sup.1 and D.sup.2 are substituted or unsubstituted phenylene, substituted or unsubstituted phenylenemethyl, substituted or unsubstituted naphthylene or substituted or unsubstituted naphthylenemethyl,K.sup.1 and K.sup.2 are each the radical of a coupling component of the aminonaphthalenesulfonic acid series andL is a bridge member,are useful for dyeing and printing hydroxyl- or nitrogen-containing substrates.Type: GrantFiled: March 30, 1992Date of Patent: April 6, 1993Assignee: Basf AktiengesellschaftInventors: Hermann Loeffler, Manfred Patsch
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Patent number: 5196518Abstract: 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: GrantFiled: August 28, 1991Date of Patent: March 23, 1993Assignee: Ciba-Geigy CorporationInventors: Horst Langfeld, Claudio Puebla, Gunter Sereinig
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Patent number: 5194597Abstract: 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: GrantFiled: April 30, 1991Date of Patent: March 16, 1993Assignee: Hoechst AGInventor: Wolfgang Rieper
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Patent number: 5176750Abstract: This invention is that of an azo pigment composition containing about 1 to 10 percent by weight of a nonionic alkyl polyglycoside dispersing agent. The polyglycosides useful in the invention have the general formulae:C.sub.n H.sub.2n+1 M (C.sub.6 H.sub.10 O.sub.5).sub.x Hwherein: M is an oxygen, sulfur, nitrogen phosphorous or silicon atom; n is an integer from 8 to 18, preferably 8 to 11 and X represents the number average degree of polymerization having a numerical value from about 1 to about 2. These azo pigment compositions are prepared by conducting the azo pigment coupling reaction in the presence of said alkyl polyglycoside. The resulting pigment exhibit superior application properties in water based ink systems.Type: GrantFiled: November 27, 1991Date of Patent: January 5, 1993Assignee: Hoechst Celanese CorporationInventors: Joseph Kammer, Richard Fischer
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Patent number: 5175258Abstract: A process for the preparation of photogenerating pigments which comprises the reaction of a diaminofluorenone with an alkali nitrite, an acid, and a tetrafluoroborate; thereafter reacting the resulting product with an anilide coupler; and subsequently annealing the product obtained.Type: GrantFiled: December 14, 1990Date of Patent: December 29, 1992Assignee: Xerox CorporationInventors: Kock-Yee Law, Ihor W. Tarnawskyj
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Patent number: 5160495Abstract: Monoazo dyestuffs useful for dyeing and printing hydrophobic fibers have the formula ##STR1## in which R.sup.1 denotes alkyl having 1 to 3 carbon atoms, R.sup.2 and R.sup.3 independently of one another denote alkyl having 2 to 5 carbon atoms and R.sup.4 denotes methyl or ethyl.Type: GrantFiled: October 29, 1990Date of Patent: November 3, 1992Assignee: Cassella AktiengesellschaftInventors: Ulrich Buhler, Reinhard Kuhn, Margareta Boos
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Patent number: 5151129Abstract: 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: GrantFiled: March 28, 1991Date of Patent: September 29, 1992Assignee: Ciba-Geigy CorporationInventors: Donald J. Morrison, David McGregor, James M. McCrae
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Patent number: 5144014Abstract: A monoazo lake which comprises a monoazo dye, a lake-forming metal and a water-insoluble metal salt of a rosin, and which is coated with the water-insoluble water salt of the rosin, the lake-forming metal being at least one metal selected from calcium, barium and strontium, the metal of the water-insoluble metal salt being at least one metal selected from zinc, aluminum, copper and manganese, and a process for the production of a monoazo lake coated with a water-insoluble metal salt of a rosin, which comprises carrying out the following steps (1) and (2) in the order of (1) to (2) or (2) to (1):(1) a step of forming a monoazo lake by forming a lake of a monoazo dye with a metal salt of at least one metal for formation of a lake of the monoazo dye selected from calcium, barium and strontium, and(2) a step of forming the water-insoluble metal salt of the rosin by insolubilizing the rosin with a metal salt of at least one metal for insolubilization of the rosin selected from zinc, aluminum, copper and manganese.Type: GrantFiled: August 8, 1990Date of Patent: September 1, 1992Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Hitoshi Sugamo, Nobuyuki Tomiya, Yusuke Watabe
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Patent number: 5132412Abstract: 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: GrantFiled: September 15, 1989Date of Patent: July 21, 1992Assignee: BASF AktiengesellschaftInventors: Guenter Hansen, Gunther Lamm, Helmut Reichelt, Ernst Schefczik
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Patent number: 5128454Abstract: The invention relates to a novel crystallographic modification (.beta.-modification) of the pigment of the formula I ##STR1## The .beta.-modification shows reflections in the Cu-K.sub..alpha. radiation X-ray diffraction spectrum at the following diffraction angles 2.theta. (accuracy .+-.0.2.degree.): at 21.95.degree. a maximum of high intensity, at 5.40.degree., 7.30.degree., 10.85.degree., 14.50.degree. and 27.60.degree. maxima of medium intensity and at 10.05.degree., 12.80.degree., 16.40.degree., 17.95.degree., 24.65.degree. and 25.80.degree. maxima of low intensity.The .beta.Type: GrantFiled: February 21, 1990Date of Patent: July 7, 1992Assignee: Hoechst AktiengesellschaftInventor: Heinrich Frolich
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Monoazo pigments derived from diazotized di- or trichloroanilines, preparation thereof and their use
Patent number: 5086168Abstract: 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: GrantFiled: September 5, 1990Date of Patent: February 4, 1992Assignee: Hoechst AktiengesellschaftInventor: Wolfgang Rieper -
Patent number: 5068319Abstract: The present invention relates to dyestuffs soluble in organic solvents having the structure: ##STR1## wherein R is CF.sub.3 or phenyl, R.sub.1 and R.sub.2 are the same or different substituent groups selected from the group consisting of hydrogen, hydroxy, halogen, C.sub.1 to C.sub.3 alkyl and C.sub.1 to C.sub.4 alkoxy, R.sub.3 is selected from the groups consisting of hydrogen, C.sub.1 to C.sub.3 alkyl, C.sub.1 to C.sub.3 alkoxy, COOH, and COOR.sub.5 wherein R.sub.5 is C.sub.1 to C.sub.4 alkyl, R.sub.6 is selected from the group consisting of hydrogen, sulfonyl, C.sub.1 to C.sub.3 alkyl, C.sub.1 to C.sub.3 alkoxy and halogen, and n is zero or a whole number ranging from 1 to 3. The dyestuffs of the invention are useful as light absorbers or antihalation agents in photosensitive compositions. They may also be used as dyeing agents for paper, fibers or films and as components in printing ink formulations.Type: GrantFiled: March 29, 1990Date of Patent: November 26, 1991Assignee: Hoechst Celanese CorporationInventors: David M. Brown, Robert E. Potvin
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Patent number: 5059684Abstract: Thiazole-azo dyes of the formula ##STR1## where R.sup.1 is C.sub.1 -C.sub.12 -alkyl, which may be interrupted by oxygen atoms, phenyl, halogen, cyano or C.sub.1 -C.sub.4 -alkoxycarbonyl,R.sup.2 is formyl, cyano, C.sub.1 -C.sub.4 -alkoxycarbonyl or a radical of the formula --CH.dbd.CX.sup.1 X.sup.2, where X.sup.1 and X.sup.2 independently of each other are cyano or C.sub.1 -C.sub.4 -alkoxycarbonyl,R.sup.3 is C.sub.1 -C.sub.12 -alkyl, which may be interrupted by oxygen atoms or substituted by phenyl or phenoxy, C.sub.5 -C.sub.7 -cycloalkyl, substituted or unsubstituted phenyl, furyl, thienyl, C.sub.1 -C.sub.4 -alkylthienyl or pyridyl, andR.sup.4 and R.sup.5 independently of each other are C.sub.1 -C.sub.12 -alkyl, which may be interrupted by oxygen atoms and/or substituted,with the proviso that in at least one of R.sup.1, R.sup.4 and R.sup.5 the alkyl chain is interrupted by oxygen atoms, are useful for dyeing textile fibers.Type: GrantFiled: March 5, 1990Date of Patent: October 22, 1991Assignee: BASF AktiengesellschaftInventors: Gunther Lamm, Karl H. Etzbach, Matthias Wiesenfeldt, Guenter Hansen, Helmut Reichelt
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Patent number: 5047517Abstract: 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: GrantFiled: September 28, 1989Date of Patent: September 10, 1991Assignee: Hoechst AktiengesellschaftInventor: Walter Deucker
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Patent number: 5047516Abstract: An azo compound of the formula: ##STR1## wherein R is an non-hydrophilic aliphatic or cycloaliphatic group containing from 8 to 40 carbon atoms;m is 0 or 1;R.sup.1 is NO.sub.2, CN or COOR.sup.2 ;R.sup.2 is H or C.sub.1-4 -alkyl;n is from 1 to 4 andR.sup.3 is H, a metal or a group containing a tetravalent N atom.The compound has non-linear optical properties which make it suitable for use in an optical element such as a waveguide, for altering the characteristics of light passing through the element.Type: GrantFiled: May 5, 1988Date of Patent: September 10, 1991Assignee: Imperial Chemical Industries PLCInventors: Simon Allen, Paul F. Gordon
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Patent number: 5037966Abstract: 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: GrantFiled: February 28, 1990Date of Patent: August 6, 1991Assignee: Ciba-Geigy CorporationInventor: Rudolf Naef
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Patent number: 5037964Abstract: (i) Metal-free compounds of the formula ##STR1## These compounds are useful as dyes for paper and textiles.Type: GrantFiled: October 17, 1986Date of Patent: August 6, 1991Assignee: Sandoz Ltd.Inventors: Helmut A. Moser, Roland Wald
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Patent number: 5026831Abstract: 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: GrantFiled: November 10, 1988Date of Patent: June 25, 1991Assignee: Hoechst AktiengesellschaftInventors: Rudiger Jung, Reinhold Deubel
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Patent number: 5024698Abstract: Monoazo pigments are provided which have improved properties achieved by incorporating certain azomethine compounds. The pigment compositions are prepared by reacting a primary amine-terminated alkylene oxide polymer and an acetoacetanilide to form an azomethine coupler and subsequently preparing the monoazo pigment composition by reacting the desired diazo component and coupling component in the presence of the azomethine coupler so as to form an azomethine composition of matter and the desired pigment.Type: GrantFiled: March 22, 1990Date of Patent: June 18, 1991Assignee: Sun Chemical CorporationInventors: Russell J. Schwartz, Manuel Z. Gregorio
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Patent number: 5011917Abstract: 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: GrantFiled: October 10, 1989Date of Patent: April 30, 1991Assignee: Hoechst AktiengesellschaftInventors: Konrad Opitz, Marcos Segal
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Patent number: 5003051Abstract: 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: GrantFiled: August 23, 1989Date of Patent: March 26, 1991Assignee: Ciba-Geigy CorporationInventors: Ulrich Schlesinger, Peter Loew, Alois Puntener
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Patent number: 5001226Abstract: 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: GrantFiled: December 19, 1989Date of Patent: March 19, 1991Assignee: Sandoz Ltd.Inventors: Helmut A. Moser, Roland Wald
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Patent number: 4996302Abstract: 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: GrantFiled: December 7, 1988Date of Patent: February 26, 1991Assignee: Ciba-Geigy CorporationInventor: Horst Langfeld
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Patent number: 4996304Abstract: 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: GrantFiled: February 23, 1990Date of Patent: February 26, 1991Assignee: Ciba-Geigy CorporationInventor: Athanassios Tzikas
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Patent number: 4985045Abstract: 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: GrantFiled: October 30, 1989Date of Patent: January 15, 1991Assignee: Cassella AktiengesellschaftInventors: Ulrich Buhler, Klaus Hofmann
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Patent number: 4960873Abstract: 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: GrantFiled: March 9, 1989Date of Patent: October 2, 1990Assignee: BASF AktiengesellschaftInventors: Guenter Hansen, Gunther Lamm, Helmut Reichelt, Ernst Schefczik
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Patent number: 4939242Abstract: 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: GrantFiled: March 25, 1988Date of Patent: July 3, 1990Assignee: Hoechst AktiengesellschaftInventors: Konrad Opitz, Marcos Segal
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Patent number: 4935502Abstract: 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: GrantFiled: August 22, 1989Date of Patent: June 19, 1990Assignee: Hoechst AktiengesellschaftInventors: Rudolf Kuhne, Heinrich Hamal
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Patent number: 4933436Abstract: 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: GrantFiled: January 27, 1987Date of Patent: June 12, 1990Assignee: Bayer AktiengesellschaftInventors: Joachim Wolff, Karl-Heinz Wolf, Reinhold M. Klipper