Replacement Of Halogen By Amino Nitrogen Patents (Class 534/598)
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Dyes Comprising [(4-[2-Amino-3,6-Disulpho-8-Hydroxynaphth-1-Ylazo]Anilino)- 1,3,5-Triazinyl] Moities
Publication number: 20080233289Abstract: A dyestuff according to formula (1) or a salt thereof wherein the substituents have the definitions as defined in claim 1. The dyestuffs are useful for dyeing or printing nitrogen-containing or hydroxy-group-containing organic substrates and for the production of (ink-jet) printing inks.Type: ApplicationFiled: September 23, 2004Publication date: September 25, 2008Inventor: Markus Gisler -
Patent number: 7041856Abstract: There are disclosed a process for producing a coupling compound of formula (1): (Y—)(n?1)R1—R2—(R1)(n??1),??(1) wherein R1 and R2 independently represent a substituted or unsubstituted aryl group, which process is characterized by reacting an unsaturated organic compound of formula (2): n?(R1X1n)??(2) wherein n, n?, and R1 are the same as defined above, and X1 is the same or different and independently represents a leaving group and bonded with a sp2 carbon atom of R1 group, with a boron compound of formula (3): m{R2(BX22)n?}??(3) wherein R2 and n? are the same as defined above, X2 represents a hydroxy group, an alkoxy group, in the presence of a catalyst containing (A) a nickel compound, and (B) a nitrogen-containing cyclic compound, and the catalyst.Type: GrantFiled: October 22, 2002Date of Patent: May 9, 2006Assignee: Sumitomo Chemical Company, LimitedInventors: Tamon Itahashi, Takashi Kamikawa
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Publication number: 20030162950Abstract: There are disclosed a process for producing a coupling compound of formula (1):Type: ApplicationFiled: October 22, 2002Publication date: August 28, 2003Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Tamon Itahashi, Takashi Kamikawa
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Patent number: 6504016Abstract: Reactive dyes of the formula (1) wherein the variables are as defined in the specification are especially suitable for dyeing cotton and yield dyeings having good all-round fastness properties.Type: GrantFiled: November 13, 2001Date of Patent: January 7, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: Athanassios Tzikas, Bruno Cortese
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Patent number: 6437104Abstract: A process for preparing disazo condensation pigments by diazotization of an aromatic amine, azo coupling with a coupling component to form an azocarboxylic acid or azodicarboxylic acid, formation of an azocarbonyl chloride or azodicarbonyl dichloride and condensation of the azocarbonyl chloride with an aromatic diamine or of the azodicarbonyl dichloride with an aromatic amine comprises effecting the acyl chloride formation and/or the condensation and optionally the diazotization and optionally the azo coupling in a microreactor.Type: GrantFiled: June 28, 2001Date of Patent: August 20, 2002Assignee: Clariant GmbHInventors: Uwe Nickel, Klaus Kund, Frank Alfter
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Patent number: 6130319Abstract: A flocculating dye reduces bleed between two inks when they are applied side by side. A first ink comprises the flocculating dye which flocculates the dispersant-pigment of the second ink.Type: GrantFiled: April 3, 1998Date of Patent: October 10, 2000Assignee: Lexmark International, Inc.Inventors: James F. Feeman, Jing X. Sun
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Patent number: 5872228Abstract: Reactive dyestuffs of the formula (I) ##STR1## wherein A denotes the radical of a diazo component andX is a fibre-reactive heterocyclic radicalare obtained by hydrolysis of maleylated azo dyestuffs of the formula (IV) ##STR2## and subsequent reaction with reactive components of the formula X-Hal without intermediate isolation, the other substituents having the meaning given in the description.Type: GrantFiled: August 5, 1997Date of Patent: February 16, 1999Assignee: Bayer AGInventor: Klaus Kunde
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Patent number: 5844101Abstract: The novel dyestuffs of the formula (I) ##STR1## in which the substituents R and X have the meaning given in the description, are outstandingly suitable for dyeing cellulosic materials in blue color shades which are particularly fast to light.Type: GrantFiled: September 17, 1997Date of Patent: December 1, 1998Assignee: Bayer AktiengesellschaftInventor: Klaus Kunde
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Patent number: 5616694Abstract: A compound of Formula (1) and salts thereof wherein the variables are as defined in the specification:Ar.sup.1 N.dbd.N-J-X-L-X-J-N.dbd.NAr.sup.2 (1)A compound of Formula (1) is suitable for use in the coloration of cellulosic substrates, such as paper, to give bright prints with good light and water fastness. It is especially suitable for use in the printing of paper by non-impact printing techniques, such as ink jet printing, especially thermal ink jet printing.Type: GrantFiled: July 12, 1995Date of Patent: April 1, 1997Assignee: Zeneca LimitedInventors: Ronald W. Kenyon, Prahalad M. Mistry
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Patent number: 5541302Abstract: Water-soluble disazo compounds, preparation thereof and use thereof as dyes There are described disazo compounds of the formula (1) ##STR1## where D is phenyl or naphthyl, R.sup.1 is hydrogen, lower alkyl, lower alkoxy, carboxyl, halogen, lower alkanoylamino or benzoylamino, R.sup.2 is hydrogen or lower alkyl, M is hydrogen or a salt-forming metal, m is 1, 2 or 3, n is 1 or 2, and R is hydrogen or lower alkyl. The compounds (1) have fiber-reactive properties and are used as dyes for dyeing and printing amino- and/or hydroxy-containing material, in particular fiber material, such as wool, silk and synthetic polyamide and also cellulose fiber materials, such as cotton; the dyeings and prints obtained are strong, fast and reddish brown.Type: GrantFiled: May 31, 1995Date of Patent: July 30, 1996Assignee: Hoechst AktiengesellschaftInventors: Andreas von der Eltz, Werner H. Russ
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Patent number: 5519121Abstract: Novel dyestuffs of the formula (I) ##STR1## in which DK denotes a radical of the formula ##STR2## where m is 1 or 2 and DK' denotes a radical of the formula ##STR3## where n is 1 or 2 R.sub.1 represents hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkyl,R.sub.2 represents hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,R.sub.3 represents substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -acylamino andR.sub.4 represents substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl.have now been found.The invention also relates to a process for their preparation and to their use for dyeing/coloring and printing textiles and paper, in particular in printing inks containing these dyestuffs.Type: GrantFiled: February 24, 1995Date of Patent: May 21, 1996Assignee: Bayer AktiengesellschaftInventors: Gerd-Friedrich Renner, Peter Wild, Karin Hassenruck
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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: 5498700Abstract: Reactive dyestuffs of the formula ##STR1## produce bluish red dyes having excellent fastness properties on hydroxyl- and amido-containing fibre material.Type: GrantFiled: September 1, 1994Date of Patent: March 12, 1996Assignee: Bayer AktiengesellschaftInventors: Hermann Henk, Wilfried Hansmann
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Patent number: 5420255Abstract: A process for the continuous reaction of halogenopyrimidines with amines, a halogenopyrimidine and an aqueous amine solution or suspension being passed into a reactor and the reaction product being subsequently conducted away, is described, characterized in that the starting materials are introduced into the reactor simultaneously and continuously with intensive mixing.Type: GrantFiled: February 22, 1994Date of Patent: May 30, 1995Assignee: Bayer AktiengesellschaftInventors: Siegbert Arnold, Hans-Georg Frosch, Manfred Hoppe, Wolfgang Mullers, Richard Sommer
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Patent number: 5412078Abstract: The reactive dyestuffs of the formula ##STR1## wherein the substituents have the meaning given in the description, are particularly suitable for dyeing naturally occurring and synthetic materials containing OH groups and/or amide groups.Type: GrantFiled: January 26, 1993Date of Patent: May 2, 1995Assignee: Bayer AktiengesellschaftInventors: Thomas Eizenhofer, Wolfgang Harms, Karl-Josef Herd
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Patent number: 5410027Abstract: Fiber-reactive formazan dyes are prepared by diazotizing a protectively formylated hydroxyphenylenediamine, coupling with a hydrazone compound, metallizing, eliminating the protective group, and reacting with a halotriazine and optionally thereafter with an amine or a hydroxy compound via novel aminophenol intermediates.Type: GrantFiled: June 11, 1993Date of Patent: April 25, 1995Assignee: BASF AktiengesellschaftInventors: Claus Marschner, Manfred Patsch
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Patent number: 5300633Abstract: Azo compounds of the formula D.sup.o --N.dbd.N--K.sup.o, in which D.sup.o is a radical of the formula (2), (2a) or (2b) ##STR1## in which Y is a substituent which can be eliminated by alkali to form the vinyl group, X is chlorine or bromine and R is hydrogen, lower alkyl, phenyl or halogen, and K.sup.o is the radical of a coupling component or another radical which contains azo groups, K.sup.o containing a group of the formula --N(R.sup.o)--Z, in which R.sup.o is hydrogen or lower alkyl and Z is a radical of the formula ##STR2## in which A is halogen or cyanoamido, R.sup.20 is hydrogen or lower alkyl, and R.sup.21 has one of the meanings given for R.sup.20, or is an optionally methyl-substituted cycloalkylene radical, or is a phenyl radical, or in which R.sup.20 and R.sup.21, together with the nitrogen atom and if appropriate one or two further hetero groups, can form a 5- or 6-membered heterocyclic radical.Type: GrantFiled: May 8, 1992Date of Patent: April 5, 1994Assignee: Hoechst AktiengesellschaftInventors: Jorg Dannheim, Werner H. Russ
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Patent number: 5298609Abstract: Compounds of formula I ##STR1## wherein R is a radical of formula --OR.sub.3 or --NHR.sub.3, A is a radical of formula II or III ##STR2## and B is a radical of formula ##STR3## wherein n is 1 or 2,R.sub.1 is --H or --Cl,R.sub.2 is --H, halogen, --NO.sub.2, --CN, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --CF.sub.3, C.sub.2 -C.sub.5 alkoxycarbonyl, --CONH--phenyl, --NHCO-phenyl or phenoxy, each unsubstituted or substituted in the phenyl nucleus by one or two chlorine atoms or by one or two methyl, methoxy or ethoxy groups,R.sub.3 is C.sub.5 -C.sub.12 cycloalkyl, which is unsubstituted or substituted by 1 to 3 C.sub.1 -C.sub.4 alkyl or C.sub.5 -C.sub.6 cycloalkyl groups,R.sub.4 and R.sub.5 are each independently of the other --H, halogen, --NO.sub.2, --CN, --CF.sub.3, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy,R.sub.6 is --H, --Cl, --Br, --CH.sub.3 or --OCH.sub.3, andX is --H, --Br, --OCH.sub.3, --CN or --NO.sub.2,are suitable for use as pigments, especially for colouring polyolefins.Type: GrantFiled: July 14, 1993Date of Patent: March 29, 1994Assignee: Ciba-Geigy CorporationInventor: Stefan Hari
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Patent number: 5298607Abstract: The invention provides reactive dyes of the formula ##STR1## wherein D is a mono- or polyazo, metal complex azo, anthraquinone, phthalocyanine, formazane, dioxazine or stilbene dye which contains sulfo groups, R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.2 is hydrogen, methyl or ethyl, X is a radical of the formula --SO.sub.2 CH.sub.2 CH.sub.2 Cl, --SO.sub.2 CH.dbd.CH.sub.2, --SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H, --SO.sub.2 CH.sub.2 CH.sub.2 OPO.sub.3 H or --N(R.sub.3)SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H, and R.sub.3 is hydrogen, methyl or ethyl, and the benzene or naphthalene radical is not further substituted or is further substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.Type: GrantFiled: May 26, 1993Date of Patent: March 29, 1994Assignee: Ciba-Geigy CorporationInventor: Herbert Seiler
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Patent number: 5270456Abstract: Thiopheneazo dye I which are chiefly useful as disperse dyes for dyeing textile material, in particular polyesters, have the formula ##STR1## where the substituents are as defined in the description.Type: GrantFiled: July 10, 1991Date of Patent: December 14, 1993Assignee: BASF AktiengesellschaftInventors: Erwin Hahn, Guenter Hansen, Karl-Heinz Etzbach, Helmut Reichelt, Ernst Schefczik, Sabine Greuttner, Helmut Degen
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Patent number: 5239063Abstract: 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: GrantFiled: January 9, 1992Date of Patent: August 24, 1993Assignee: Bayer AktiengesellschaftInventors: Manfred Hoppe, Martin Michna, Karl-Josef Herd, Frank-Michael Stohr
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Patent number: 5227476Abstract: Compounds of the formula ##STR1## and salts thereof, wherein R.sub.1 is hydrogen, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,R.sub.2 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, (C.sub.1-4 alkyl)carbonylamino or --NHCONH.sub.2, andW is -NR.sub.3 -B.sub.1 -NR.sub.3 -, ##STR2## wherein B.sub.1 is linear or branched C.sub.2-6 alkylene, linear or branched C.sub.2-6 alkylene interrupted by --O-- or --NR.sub.3 -- or linear or branched C.sub.3-6 alkylene monosubstituted or disubstituted by hydroxy, with the proviso that the hydroxy groups of any linear or branched C.sub.3-6 alkylene disubstituted by hydroxy are bound to different carbon atoms, andR.sub.4 is linear or branched C.sub.2-4 alkylene,whereineach R.sub.3 is independently hydrogen, C.sub.1-4 alkyl or C.sub.1-4 alkyl substituted by hydroxy, halo, cyano, sulfo, sulfato or carboxy,with the provisos that the --N.dbd.Type: GrantFiled: August 21, 1990Date of Patent: July 13, 1993Assignee: Sandoz Ltd.Inventors: Paul Doswald, Werner Koch
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Patent number: 5227475Abstract: Water-soluble dyestuffs which correspond to the formula (1) given below, have fiber-reactive properties and dye synthetic and natural materials, in particular fiber materials, containing hydroxyl and/or carboxamide groups, such as wool and in particular cellulose fiber materials, in deep shades ##STR1## in which: F is the radical of a dyestuff, such as of an azo dyestuff, heavy metal complex azo dyestuff, anthraquinone dyestuff or phthalocyanine dyestuff,R.sup.x is hydrogen or lower alkyl, which can be substituted by halogen, hydroxyl, cyano, lower alkoxy, lower alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato;n is the number 1 or 2; andQ is a group of the formula ##STR2## in whichR.sup.Type: GrantFiled: January 10, 1992Date of Patent: July 13, 1993Assignee: Hoechst AktiengesellschaftInventors: Holger M. Buch, Reinhard Hahnle, Hartmut Springer
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Patent number: 5166325Abstract: The new polyazo reactive dyestuffs of the formula ##STR1## in which the substituents have the meaning given in the description are highly suitable for the dyeing or printing of hydroxyl- or amido-containing materials. The dyeings and prints obtained are distinguished by high fibre-dyestuff bonding stability and by particularly good stability to oxidizing agents.Type: GrantFiled: April 25, 1991Date of Patent: November 24, 1992Assignee: Bayer AktiengesellschaftInventors: Karl-Josef Herd, Hermann Henk, Karl-Heinz Schundehutte, Frank-Michael Stohr
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Patent number: 5118737Abstract: A water-soluble dye, free from cellulose reactive groups, of the formula: ##STR1## wherein R.sup.1 is --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H,R.sup.2 is H or --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H, orR.sup.1 and R.sup.2 together with the nitrogen atom form a morpholine ringa and b are different and from 1 to 8m is from 1 to 10;n is from 0 to 9;M is H, ammonium, or a monovalent metal;X (i) NR.sup.1 R.sup.2, (ii) NR.sup.3 R.sup.4, in which R.sup.3 and R.sup.Type: GrantFiled: June 22, 1990Date of Patent: June 2, 1992Assignee: Canon Kabushiki KaishaInventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
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Patent number: 5091515Abstract: A new process for the preparation of substituted 2,4-diamino-6-flurotriazines of the formula ##STR1## in which the substituents have the meanings given in the description, comprises reacting ammonium salts of the formula ##STR2## in an aqueous medium at pH values of about 2.5-10 with 2,4,6-trifluorotriazine in a continuous process. The reaction products can be converted to dyestuffs without isolating the intermediates.Type: GrantFiled: May 3, 1990Date of Patent: February 25, 1992Assignee: Bayer AktiengesellschaftInventors: Karl J. Herd, Hans-Georg Frosch, Hermann Henk, Wolfgang Mullers, Frank-Michael Stohr
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Patent number: 5079347Abstract: Disazo compounds conforming to a general formula (1) shown below which have fiber-reactive dye properties and dye hydroxy- and/or carboxamido-containing fiber materials, such as wool and in particular cellulose, in strong fast shades. ##STR1## where R is a hydrogen atom or a sulfo group,R.sup.1 is a hydroxy group, a methoxy group or an ethoxy group,M is a hydrogen atom or an alkali metal,X is a chlorine atom or a fluorine atom,Y is a chlorine atom or an amino group or a group of the general formula (2) ##STR2## where R* is a hydrogen atom or a methyl or ethyl group,n is zero, 1 or 2,R.sup.2 is a hydrogen atom or a sulfo group or a .beta.-sulfatoethylsulfonyl group or a vinylsulfonyl group, andR.sup.3 is a sulfo group or a .beta.-sulfatoethylsulfonyl group or a vinylsulfonyl group,it being possible for R.sup.2 and R.sup.3 to be identical to or different from each other.Type: GrantFiled: December 6, 1988Date of Patent: January 7, 1992Assignee: Hoechst AktiengesellschaftInventor: Holger M. Buch
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Patent number: 5068447Abstract: Aromatic carbonyl compounds, in particular arylene ether ketones, are prepared by reacting an appropriate reagent system in the presence of free Lewis acid and a complex between a Lewis acid, for example, aluminum trichloride, and an inorganic salt controlling agent, for example, lithium chloride, and, optionally, a diluent, such as methylene chloride. The process is particularly advantageous for the preparation of substantially or all para-linked arylene ether ketones as the presence of the Lewis acid/Lewis base complex markedly reduces alkylation and ensures the substantial absence of ortho substitution.Type: GrantFiled: July 6, 1990Date of Patent: November 26, 1991Assignee: Raychem CorporationInventors: Heinrich C. Gors, Patrick J. Horner, Viktors Jansons
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Patent number: 5053494Abstract: A polyazo compound of the following formula, ##STR1## wherein F is a bisazo or trisazo dye moiety, R.sub.1, R.sub.2 and R.sub.3 are independently of one another are each hydrogen or alkyl, B.sub.1 and B.sub.2 independently of one another are each phenylene or naphthylene, Y.sub.1 and Y.sub.2 independently of one another are each --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 L in which L is group capable of being split by the action of an alkali. The compound is useful for dyeing or printing fiber materials to give dyed or printed products with superior dye performance such as build-up property.Type: GrantFiled: October 20, 1989Date of Patent: October 1, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Takashi Omura, Naoki Harada, Hirokazu Sawamoto
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Patent number: 5047514Abstract: Reactive dyes which contain at least one radical of the formula--SO.sub.2 --CH.dbd.CH.sub.2 (1a)or--SO.sub.2 --CH.sub.2 CH.sub.2 --X (1b)and at least one radical of the formula ##STR1## in which X is an inorganic or organic radical detachable under alkaline conditions, R is hydrogen or substituted or unsubstituted C.sub.1-4 -alkyl, Y is oxygen or sulfur and R.sub.1 is a substituted or unsubstituted aliphatic radical, give dyeings or prints having good fastness properties.Type: GrantFiled: November 5, 1987Date of Patent: September 10, 1991Assignee: Ciba-Geigy CorporationInventors: Peter Scheibli, Karl Seitz
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Patent number: 5037967Abstract: 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: GrantFiled: November 7, 1989Date of Patent: August 6, 1991Assignee: Ciba-Geigy CorporationInventors: Angelo D. Casa, Peter Liechti, Max Dempfle
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Patent number: 5023326Abstract: 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: GrantFiled: November 9, 1989Date of Patent: June 11, 1991Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Herbert Seiler
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Patent number: 5021558Abstract: Water-soluble fiber-reactive azo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylemthane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dyes which contain once or twice the group of the general formula ##STR1## in which: R.sup.x and R.sup.z are, independently of one another, hydrogen or lower alkyl, which can be substituted by halogen, hydroxyl, cyano, lower alkoxy, lower alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato;W is fluorine, chlorine, bromine, sulfo, phenylsulfonyl or alkylsulfonyl of 1 to 4 carbon atoms;Y is vinyl, .beta.-substituted, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-alkanoyloxyethyl of 2 to 5 carbon atoms in the alkanoyl radical, .beta.-benozoyloxyethyl, .beta.-(sulfobenzoyloxy)ethyl, .beta.-(p-toluenesulfonyloxy)ethyl or .beta.-halogenoethyl.Type: GrantFiled: March 20, 1990Date of Patent: June 4, 1991Assignee: Hoechst AktiengesellschaftInventor: Holger M. Buch
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Patent number: 5015731Abstract: 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-solubilType: GrantFiled: February 2, 1990Date of Patent: May 14, 1991Assignee: Hoechst AktiengesellschaftInventors: Gunther Schwaiger, Hartmut Springer
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Patent number: 5003049Abstract: The compounds of the general formula (I) ##STR1## where A is a dye radical, where relevant the radicals Y independently of one another are each oxygen, sulfur, R.sup.1 --N or a direct bond, n is 1 or 2, the radicals R.sup.1 independently of one another are each hydrogen or unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl and Z is a bridge member, are very useful for dyeing hydroxyl-containing textile material.Type: GrantFiled: February 8, 1989Date of Patent: March 26, 1991Assignee: BASF AktiengesellschaftInventors: Udo Bergmann, Alfred Hackenberger, Manfred Patsch
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Patent number: 5003053Abstract: 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: GrantFiled: March 19, 1990Date of Patent: March 26, 1991Assignee: Hoechst AktiengesellschaftInventors: Hartmut Springer, Walter Helmling, Ludwig Schlafer, Werner H. Russ
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Patent number: 5001229Abstract: 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: GrantFiled: December 16, 1988Date of Patent: March 19, 1991Assignee: Bayer AktiengesellschaftInventors: Gunter Franke, Peter Wild
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Patent number: 4968783Abstract: 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: GrantFiled: January 19, 1989Date of Patent: November 6, 1990Assignee: Ciba-Geigy CorporationInventors: Karl Seitz, Gert Hegar
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Patent number: 4963659Abstract: Reactive dyes which are particularly suitable for the dyeing or printing of cellulose-containing fiber materials by the exhaust process or by the continuous process and give, at a high color yield, dyeings and prints having good fastness properties, having the formula ##STR1## in which D.sub.1 and D.sub.2, independently of one another, are each a radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye; R.sub.1, R.sub.2, B.sub.1 and B.sub.2, independently of one another, are hydrogen or alkyl having 1 to 4 carbon atoms, which is unsubstituted or substituted by halogen, hydroxyl, cyano, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato; X is fluorine, chlorine, bromine, sulfo, C.sub.1 -C.sub.Type: GrantFiled: March 14, 1989Date of Patent: October 16, 1990Assignee: Ciba-Geigy CorporationInventor: Athanassios Tzikas
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Patent number: 4918169Abstract: Reactive dyes suitable for dyeing and printing cellulosic fiber materials by the cold pad-batch process having the formula ##STR1## wherein Fa is a monoazo or polyazo, metal complex azo, anthraquinone, phthalocyanine, formazane, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, napthoquinone, pyrenequinone or perylene-tetracarbimide dye radical, X is halogen, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl, a sulfonic acid or phosphonic acid group or a quaternized ammonium group, r is 1 or 2, R is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy or phenyl, and A is a radical of the formula ##STR2## wherein R' is hydrogen, C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy or phenyl, C.sub.5 -C.sub.Type: GrantFiled: August 19, 1988Date of Patent: April 17, 1990Assignee: Ciba-Geigy CorporationInventor: Karl Hoegerle
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Patent number: 4918183Abstract: The invention relates to monoazo dyes of the formula ##STR1## wherein K is the radical of a coupling component of the benzene, naphthalene or heterocyclic series, and R is hydrogen, halogen, carboxy, a C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.2 -C.sub.6 alkanoylamino, C.sub.1 -C.sub.6 alkylsulfonylamino, C.sub.1 -C.sub.6 alkylsulfonyl, phenyl(C.sub.1 -C.sub.4)alkylsulfonyl or naphthyl(C.sub.1 -C.sub.4)alkylsulfonyl or benzoyl radical, which radicals may be further substituted, or is a ##STR2## group, wherein each of R.sub.1 and R.sub.2 independently of the other is hydrogen or a C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or naphthyl radical, which radicals may be further substituted, and wherein X is hydrogen, halogen or a C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.2 -C.sub.6 alkanoylamino or C.sub.1 -C.sub.6 alkylsulfonylamino radical, which radicals may be further substituted.These dyes give dyeings of good light- and wetfastness properties on polyamide material.Type: GrantFiled: October 24, 1985Date of Patent: April 17, 1990Assignee: Ciba-Geigy CorporationInventor: Rudolf Hurter
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Patent number: 4916215Abstract: Water-soluble disazo compounds of the general formula ##STR1## in which D.sub.1 and D.sub.2 are each a phenylene or naphthylene radical which can be substituted by 1 or 2 substituents from the group consisting of 1 chlorine, 1 bromine, 2 sulfo, 2 carboxyl, 2 alkyl of 1 to 4 carbon atoms and 2 alkoxy of 1 to 4 carbon atoms, R' and R" each denote an amino or hydroxyl group, R.sup.+ and R* each represent methyl, carboxyl or lower carbalkoxy, R.sup.1 and R.sup.3 are each hydrogen, lower alkyl, lower alkoxy, chlorine or bromine, R.sup.2 and R.sup.4 each denote hydrogen, lower alkyl, lower alkoxy or chlorine, X denotes a vinyl, .beta.-sulfatoethyl,.beta.-thiosulfatoethyl or .beta.-chloroethyl group and Y is a chlorine, fluorine or bromine atom or a sulfo, hydroxyl, aliphatic or aromatic ether group or thioether group or a primary, secondary or tertiary amino group.Type: GrantFiled: March 29, 1988Date of Patent: April 10, 1990Assignee: Hoechst AktiengesellschaftInventors: Ernst Hoyer, Rudolf Fass
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Patent number: 4914190Abstract: Disperse dyes of the formula ##STR1## in which X is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen, 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- or 6-ring, B is a straight-chain or branched C.sub.2 -C.sub.6 alkylene radical, Z is a bridge member of the formula ##STR2## or a direct bond and A is a radical of the formula ##STR3## which radicals are unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen or nitro are suitable in particular for dyeing textile material made of polyester fibers.Type: GrantFiled: March 11, 1988Date of Patent: April 3, 1990Assignee: Ciba-Geigy CorporationInventors: Peter Liechti, Angelo Della Casa
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Patent number: 4910299Abstract: Disperse dyes suitable for dyeing textile material composed of polyester dyes of the formula ##STR1## in which D is the radical of a substituted or unsubstituted, homocyclic or heterocyclic diazo component belonging to the series comprising thienyl, thiazolyl, isothiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, benzothiazolyl, benzoisothiazolyl, pyrazolyl, imidazolyl or phenyl,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 ring or 6-membered ring,B is a l inear or branched C.sub.2 -C.sub.6 -alkylene radical,W is halogen, C.sub.Type: GrantFiled: December 2, 1987Date of Patent: March 20, 1990Assignee: Ciba-Geigy CorporationInventors: Angelo D. Casa, Peter Liechti, Max Dempfle
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Patent number: 4906739Abstract: 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: GrantFiled: June 15, 1989Date of Patent: March 6, 1990Assignee: Ciba-Geigy CorporationInventors: Herbert Seiler, Gert Hegar
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Patent number: 4906738Abstract: Water-soluble monoazo compounds of the general formula (1) ##STR1## in which D is a phenyl radical or naphthyl radical, either of which is substituted and mandatorily contains at least one group which imparts solubility in water and D is substituted, for example by 1, 2 or 3 substituents which can be selected from the set consisting of 1 sulfamoyl, 1 carbamoyl, 1 trifluoromethyl, 1 benzothiazol-2-yl, 1 sulfobenzothiazol-2-yl, 1 methylbenzothiazol-2-yl, 1 methylsulfobenzothiazol-2-yl, 1 styryl, 1 nitrostyryl, 1 sulfostyryl and 1 nitrosulfostyryl group and, preferably, three sulfo groups, two carboxy groups, two alkyl groups of 1-4 C atoms, two alkoxy groups of 1-4 C atoms, 1 bromine atom and two chlorine atoms and one or two groups of the formula --SO.sub.2 --Z with Z of the meaning below, and the group --SO.sub.2 --Z can also be bonded to one of the substituents and Z represents the .beta.Type: GrantFiled: April 15, 1985Date of Patent: March 6, 1990Assignee: Hoechst AktiengesellschaftInventors: Folker Kohlhaas, Fritz Meininger, Hans H. Steuernagel
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Patent number: 4906736Abstract: Water-soluble copper complex formazan compounds which conform to the general formula (1) below and have useful fiber-reactive dye properties and dye carboxamido- and/or hydroxy-containing material, in particular cellulose fibers, in fast blue shades. ##STR1## in which: M is hydrogen or a salt-forming metal atom,k, m and n each denote the number zero, 1 or 2, the sum (k+m+n) being equal to 1 to 4,A is a benzene or napththalene ring which additionally can contain the fiber-reactive group --NH--Q and further substituents,B is a benzene or naphthalene ring which additionally contains the fiber-reactive group --NH--Q and further substituents,D is substituted or unsubstituted alkylene of 1 to 8 carbon atoms or is a benzene or naphthalene ring having optionally additional substituents or is a heterocyclic radical,X is a sulfo group or an oxy or carbonyloxy group,r is the number 1 or 2,Q is a radical of the formula (2) ##STR2## in which Y is halogen, Z is vinyl or a .beta.Type: GrantFiled: February 23, 1988Date of Patent: March 6, 1990Assignee: Hoechst AktiengesellschaftInventors: Gunther Schwaiger, Hartmut Springer, Werner H. Russ
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Monoazo compound having two vinylsulfone type fiber reactive groups through triazinyl bridging group
Patent number: 4904766Abstract: A monoazo compound represented by the following formula in a free acid form, ##STR1## wherein D is a sulfophenyl or sulfonaphthyl, R.sub.1, R.sub.2 and R.sub.3 are independently hydrogen or alkyl; B.sub.1 and B.sub.2 are independently phenylene, naphthylene, or alkylene, provided that at least one of B.sub.1 and B.sub.2 is phenylene or naphthylene, Y.sub.1 and Y.sub.2 are independently vinyl or --CH.sub.2 CH.sub.2 Z in which Z is splittable by the action of an alkali, and n is 0 or 1, and the monoazo compound is useful for dyeing or printing fiber materials to obtain dyed or printed products of extremely deep scarlet color excellent in various fastness with superior build-up property.Type: GrantFiled: October 13, 1987Date of Patent: February 27, 1990Assignee: Sumitomo Chemical Company, LimitedInventors: Kazufumi Yokogawa, Toshihiko Morimitsu, Naoki Harada, Takashi Omura, Sadanobu Kikkawa -
Patent number: 4879372Abstract: A triazine compound having a dye moiety, a sym-monohalotriazine moiety and an aminobenzoylamine moiety, which is represented, for example, by the following formula, ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are independently hydrogen or alkyl, A is phenylene or naphthylene, D is a dye moiety, X is chloro or fluoro, Z is --SO.sub.2 CH.dbd.CH.sub.2, --SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H or the like, and n is 0, 1 or 2, and which is useful for dyeing or printing fiber materials such as cellulose fiber materials with superior dye performance such as build-up property to give dyed or printed products excellent is fastness properties.Type: GrantFiled: November 6, 1987Date of Patent: November 7, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Toshihiko Morimitsu, Naoki Harada, Takashi Omura
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Patent number: 4873320Abstract: Water-soluble dyes which contain one or two fiber-reactive groups of the formula ##STR1## in which each R is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, it being possible for both R to have a meaning which is identical to or different from one another, Y is the vinyl group or a group of the general formula --CH.sub.2 --CH.sub.2 --X in which X represents a substituent which can be eliminated as an anion, and m represents the number 2 or 3. These novel dyes can be used to dye hydroxy and/or carboxamide group-containing materials in particular fiber-materials, such as, in particular, cellulose fiber materials, in fast shades.Type: GrantFiled: December 15, 1987Date of Patent: October 10, 1989Assignee: Hoechst AktiengesellschaftInventors: Hartmut Springer, Manfred Kuhn, Holger M. Buch