Azo Bonded Directly To An Acyclic Carbon Which Is Bonded Directly To Two Acyclic Carbons, Each Of Which Is Double Or Triple Bonded To An Atom Patents (Class 534/700)
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Patent number: 9440927Abstract: The present invention provides a process for the preparation of substituted 3?-hydrazino-biphenyl-3-carboxylic acid compounds. The present invention further provides a process for the preparation of 3?-{N?-[1-(3,4-dimethylphenyl)-3-methyl-5-oxo -1,5-dihydro-pyrazol-4-ylidene]hydrazino}-2?-hydroxybiphenyl-3-carboxylic acid, its intermediate compounds and pharmaceutically acceptable salts thereof.Type: GrantFiled: September 12, 2012Date of Patent: September 13, 2016Assignee: Glenmark Pharmaceuticals LimitedInventors: Bhargav Krishnaji Upadhye, Shivaji Eknath Jagadale, Mukesh Soni
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Patent number: 7699898Abstract: Dye mixtures comprising one or more, such as two or three, preferably 1 or 2, dyes of the formula (1) and at least 2 dyes of the formula (2) in which Me, M, n, and V1 to V11 are as defined in claim 1, their preparation, and their use for dyeing and printing hydroxyl- and carboxamido-containing material.Type: GrantFiled: March 15, 2006Date of Patent: April 20, 2010Assignee: DyStar Textilfarben GmbH & Co. Deutschland KGInventors: Thomas Ruchser, Oliver Steinau, Andreas Giehl
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Patent number: 7297200Abstract: A dye of the formula (2) and a process for preparing the same, wherein the radicals are as defined in the specificationType: GrantFiled: February 3, 2003Date of Patent: November 20, 2007Assignee: Clariant Produkte (Deutschland) GmbHInventors: Andreas Wuzik, Josef Geisenberger, Heidemarie Menzel
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Patent number: 6756486Abstract: Disclosed are green shade yellow pigments represented by the Formula I: wherein R1 and R2 are independently selected from hydrogen, hydroxy, halogen, an alkyl group having 1 to about 4 carbon atoms, an alkoxy group having 1 to about 4 carbon atoms, a halo-alkyl group containing 1 to about 4 carbon atoms, an alkoxy carbonyl group having 1 to about 5 carbon atoms; R3 and R4 are independently selected from hydrogen, hydroxy, halogen, an alkyl group containing from 1 to about 4 carbon atoms, an alkoxy group containing from 1 to about 4 carbon atoms, and halo-alkyl groups containing from 1 to about 4 carbon atoms; and M is at least one divalent metal. Also disclosed are methods of making the green shade yellow pigments, methods of using the green shade yellow pigments, and coating compositions, ink compositions, electrostatic toner compositions, paint compositions, paper compositions, and plastic compositions containing the green shade yellow pigments.Type: GrantFiled: September 18, 2003Date of Patent: June 29, 2004Assignee: Engelhard CorporationInventors: Amrit P. Bindra, Steven A. Zamborsky
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Patent number: 6210448Abstract: 1:2 chromium complex dyes of the formula: in which R signifies C1-9-alkyl or a radical of the formula: R1 signifies C1-4-alkyl, R2 signifies hydrogen or —SO3M, R3 signifies hydrogen, methyl or methoxy, R4 signifies hydrogen, methyl, methoxy or chloro, n signifies from 0 to 3, M signifies hydrogen or a non-chromophoric cation and Kat+signifies hydrogen or a non-chromophoric cation, are suitable for dyeing artificially produced oxide layers on aluminium or aluminium alloys and so give rise to highly lightfast dyeings in yellow shades.Type: GrantFiled: November 24, 1999Date of Patent: April 3, 2001Assignee: Clariant Finance (BVI) LimitedInventor: Klaus Körte
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Patent number: 5853431Abstract: Compounds of formula (I) ##STR1## wherein R.sub.1 is H or SO.sub.3 M, ##STR2## M is hydrogen or a non-chromophoric cation and X.sup.+ is hydrogen or a non-chromophoric cation, are useful as dyes for oxidized aluminium substrates.Type: GrantFiled: November 6, 1997Date of Patent: December 29, 1998Assignee: Clariant Finance (BVI) LimitedInventor: Klaus Korte
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Patent number: 5731422Abstract: Complexes of formulae I and II ##STR1## wherein the variables are as defined in the specification are useful as dyes for, for example, the mass dyeing of plastics and for lacquers.Type: GrantFiled: June 6, 1995Date of Patent: March 24, 1998Assignee: Clariant Finance (BVI) LimitedInventors: Bansi Lal Kaul, Dominique Pflieger
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Patent number: 5698683Abstract: A process for preparing a mixed aluminium-heavy metal dyestuff complex, in which the amount of heavy metal present is 10-98% and that of aluminium is 2 to 90% comprisingi) reacting the metal free dyestuff with less than a stoichiometric amount of a heavy metal compound followed byii) reacting the product with an aluminium compound in an amount to produce a stoichiometric excess of metal (calculated on all the metal present) to form a mixed aluminium-heavy metal complex.Type: GrantFiled: May 12, 1995Date of Patent: December 16, 1997Assignee: Clariant Finance (BVI) LimitedInventors: Bansi Lal Kaul, Dominique Pflieger
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Patent number: 5602237Abstract: The invention provides a 1:2 metal complex in which at least one of the complexants is a polyazo compound of formula ##STR1## wherein --A.sub.1 --(CO).sub.p --OH signifies the radical of a diazo component of formula H.sub.2 N--A--(CO).sub.p --OH, in which the substituent --(CO).sub.p --OH is in ortho-position to the diazotizable amino group --NH.sub.2, --A-- is the ortho-bivalent radical and p signifies 0 or 1, or a modified derivative thereof,--X-- signifies an aromatic bivalent radical,--B.sub.1 signifies the radical of a coupling component HB, or a modified derivative thereof,m signifies 0 or 1,n signifies 0, 1 or 2and M signifies hydrogen or a cation, with the proviso that m+n=1 or 2,or a mixture of such complexes and to the use thereof as dyestuffs, in particular for the dyeing of a substrate dyeable with anionic dyes, especially of leather or pelts.Type: GrantFiled: March 29, 1995Date of Patent: February 11, 1997Assignee: Sandoz Ltd.Inventors: Jordi B. Barra, Jose R. Sorolla
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Patent number: 5514783Abstract: The invention provides a process for the production of azodyes and their derivatives by diazotization and coupling reactions and optionally further modification reactions, wherein a compound of formula ##STR1## in which E signifies an aromatic bivalent radical,X.sub.1 signifies hydroxy or a primary amino group,Y.sub.1 signifies hydroxy or a primary amino groupand in whichthe aminogroup linked to the --SO.sub.2 -bound phenyl radical may optionally be acylated,or a mixture of compounds of formula (I), is employed as a coupling component or/and--in the non-acylated form--as a diazo component,the invention in particular relates also to the novel dyes and their use and to the novel intermediates.Type: GrantFiled: April 28, 1995Date of Patent: May 7, 1996Assignee: Sandoz Ltd.Inventors: Jordi B. Barra, Jose R. Sorolla
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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: 5095100Abstract: Metal complex dyes comprising a metalizable azo compound represented by one of Formulas [I] through [IV]: ##STR1## In Formulas [I] through [IV], Ps represents a phosphono group in the form of a free acid or a salt; Sf represents a sulfo group in the form of a free acid or a salt; m is 0, 1 or 2. R.sup.1 represents a hydrogen atom or an amino group; X represents a hydroxyl group, an alkoxy group having a carbon number of 1 or 2 or a carboxyl group. Y represents a hydroxyl group, an alkoxy group having a carbon number of 1 or 2, a carboxyl group or a methyl group; R.sup.2 represents a hydrogen atom or a hydroxyl group; A represents a phenyl group or naphthyl group selected from the group comprising the following 1 through 4: ##STR2## In the above formulas 1 through 4, Sf has the same definition as above; n is 0, 1 or 2. R.sup.3 represents a hydroxyl group or a carboxyl group; R.sup.4 represents a hydroxyl group, a carboxyl group or an amino group; R.sup.5 and R.sup.Type: GrantFiled: June 12, 1990Date of Patent: March 10, 1992Assignee: Orient Chemical Industries, Ltd.Inventors: Takashi Ono, Tatsuya Yagyu, Katsumi Fukuda, Minako Terasaki
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Patent number: 4874849Abstract: Dyes suitable for dyeing wool, polyamide and leather in orange, brown or olive-brown shades are disclosed, the dyes having the formula ##STR1## wherein A and D are each independently of the other a benzene or napththalene radical of a diazo component, which component carries the hydroxyl or carboxyl group in the ortho-position to the azo group;B is the radical of a coupling component which carries the group X adjacent to the azo group;X is oxygen or a radical of the formula --R--, in which R is hydrogen or C.sub.1 -C.sub.4 alkyl;Y is a radical of the formula ##STR2## in which formulae R.sup.1 and R.sup.5 are each independently of the other hydrogen or sulfo, R.sup.4 is hydrogen or nitro, R.sup.6 is hydrogen, methyl, methoxy or chlorine and R.sup.2 and R.sup.3 are each independently of the other hydrogen, halogen, nitro or sulfo;Ar.sup.1 is a benzene or napththalene radical which is unsubstituted or substituted by halogen, nitro, sulfo, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.Type: GrantFiled: December 19, 1986Date of Patent: October 17, 1989Assignee: Ciba-Geigy CorporationInventors: Gerhard Back, Fabic Beffa, Ulrich Schlesinger, Alois Puntener
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Patent number: 4772687Abstract: Metal complex dyestuffs which in the form of the free acid correspond to the formula ##STR1## in which the substituents have the meaning given in the description are, depending on the meanings of the substituents, suitable for use as reactive dyestuffs for cotton, wool or polyamide, as direct dyestuffs for cotton or as pigment dyestuffs. Dyeings are obtained which have good fastness properties, in particular good wet-, light- and chlorine fastness.Type: GrantFiled: May 1, 1986Date of Patent: September 20, 1988Assignee: Bayer AktiengesellschaftInventor: Hermann Henk
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Patent number: 4723001Abstract: The invention relates to chromium complexes of the formula ##STR1## in which B is the radical of a bidentate bianionic compound, L is H.sub.2 O, NH.sub.3, alkanol, alkylamine, dialkylamine, trialkylamine or pyridine, D is a benzene or naphthalene diazo component, Y is the nitrogen atom or the CH group, K is a coupling component, R is hydrogen, alkyl or phenyl, X is a fibre-reactive group,Ka is a cation, m is 1, 2 or 3, n is 1 or 2 and k is 0 or 1.These chromium complexes are suitable for dyeing nitrogen-containing or hydroxy-containing materials and they produce level dyeings having good all-round fastness properties.Type: GrantFiled: July 24, 1986Date of Patent: February 2, 1988Assignee: CIBA-GEIGY CorporationInventors: Hans U. Schutz, Ulrich Schlesinger, Gerhard Back
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Patent number: 4668774Abstract: Novel dye salts of anionic dyes of the general formula I ##STR1## where F is a radical of an anionic dye, n is 1, 2, 3 or 4, and B.sup.1 and B.sup.2 independently of one another are each unsubstituted or substituted branched alkyl or alkyl-substituted cycloalkyl having a total of 10 to 36 carbon atoms, are very useful for dyeing solvents, printing inks or polymeric film-forming materials.Type: GrantFiled: April 23, 1985Date of Patent: May 26, 1987Assignee: BASF AktiengesellschaftInventors: Hermann Loeffler, Rainer Dyllick-Brenzinger
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Patent number: 4665162Abstract: Metal-free azo compounds of the formula ##STR1## wherein Ra is an aromatic group or an active methylene coupling component radical as defined in the specification,R.sub.t is an arylazo group or a group of the formula --Y--Z,whereinY is a direct bond or a bridging radical, andZ is a basic amino or quaternary ammonium group, ##STR2## wherein each of the variables is as defined above or below, x is a direct bond or a bridging radical,x is hydrogen, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, amino or carboxy,ring B is further unsubstituted or further substituted,d is 0, 1 or 2, andn is 0 or 1,with the provisos that (i) the compounds contain an average of at least 1.3 basic water-solubilizing groups, and (ii) the compounds are free of sulfo groups, and 1:1 and 1:2 metal complexes thereof, which metal-free compounds and metal complexes are useful as dyes for leather and paper.Type: GrantFiled: June 18, 1985Date of Patent: May 12, 1987Assignee: Sandoz Ltd.Inventors: Paul Doswald, Emil Moriconi, Helmut Moser, Horst Schmid
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Patent number: 4663441Abstract: Compounds of the formula I ##STR1## where K.sup..sym. is a cation, R is methyl or is phenyl which is unsubstituted or substituted by chlorine, bromine, methyl, methoxy or ethoxy, R.sup.1 is hydrogen, chlorine, bromine or nitro, R.sup.2 is hydrogen, chlorine, bromine, nitro, sulfamyl or hydroxysulfonyl, X and Y are each --O-- or --COO--, Z is --O-- or --NH--, D is a radical of a diazo component of the aniline or naphthylamine series and K is a radical of a coupling component, are very useful for dyeing natural and synthetic polyamide textile fibers and leather.Type: GrantFiled: September 16, 1985Date of Patent: May 5, 1987Assignee: BASF AktiengesellschaftInventor: Klaus Grychtol
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Patent number: 4652631Abstract: 1:2 chromium complex dyes suitable for dyeing nitrogen-containing materials and materials which contain hydroxyl groups, are disclosed which, in the form of the free acid, have the formula ##STR1## wherein each of the symbols independently has the following meanings: Z is nitrogen or a --CH,A is a benzene or naphthalene radical which carries the hydroxyl or carboxy ortho to the azo or azomethine group, or, if n is 1 and Z is a --CH, is the radical of an aliphatic, cycloaliphatic or aromatic aminocarboxylic acid,B and D are each independently of the other the radical of a coupling component which couples in the alpha- or o-position relative to X if Z is nitrogen, or the radical of an o-hydroxyaldehyde if Z is --CH,X is oxygen or --NR, wherein R is hydrogen or C.sub.1 -C.sub.4 alkyl, with the proviso that X must be oxygen if Z is --CH,Y is a bridge member of the formula --SO.sub.2 or --SO.sub.2 --NR--SO.sub.2 --, wherein R is hydrogen or C.sub.1 -C.sub.4 alkyl,n is 0 or 1, andp is an integer from 0 to 6.Type: GrantFiled: March 28, 1985Date of Patent: March 24, 1987Assignee: Ciba-Geigy CorporationInventors: Fabio Beffa, Ulrich Schlesinger
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Patent number: 4650859Abstract: Chrome azo-azomethine dyes are disclosed which contain a benzthiazolylphenyl or stilbenyl radical bound via an aldehyde group to the aldehyde moiety of the azomethine dyes. The dyes are particularly useful for dyeing wool, polyamide and leather.Type: GrantFiled: December 31, 1984Date of Patent: March 17, 1987Assignee: Ciba-Geigy CorporationInventor: Fabio Beffa
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Patent number: 4649194Abstract: 1:2 Metal complexes of the formula ##STR1## wherein X.sub.1 is --O-- or ##STR2## and X.sub.2 is --O-- or ##STR3## the starred atom being attached A.sub.1 or A.sub.2, respectively, A.sub.1 is a diazo component radical of the benzene series,A.sub.2 is a diazo component radical of the benzene or naphthalene series,W is --CH.sub.3 or --COOH,R is hydrogen or --SO.sub.3 H,each of B.sub.1 and B.sub.2 is independently a coupling component radical or a phenolic hydroxy group-containing coupling component radical at least one phenolic hydroxy group of which is etherified or acylated,M is iron, cobalt or chromium, andn is 1 or 2,which complexes are useful as anionic dyestuffs having olive to brown colors for substrates such as natural and regenerated cellulose, natural and synthetic polyamides, polyurethane and anodized aluminum, especially leather.Type: GrantFiled: July 27, 1983Date of Patent: March 10, 1987Assignee: Sandoz Ltd.Inventor: Heinz Wicki
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Patent number: 4625017Abstract: Metallizable azo dyes of the formula I ##STR1## wherein A is the radical of a diazo component of the benzene or naphthalene series, which diazo component contains in the o-position with respect to the azo group a metallizable hydroxyl group,R is methyl or chloromethyl, or phenyl which can be substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen,R.sub.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl,R.sub.2 is hydrogen or methyl,n is 0 or 1, andm is 0, 1, 2 or 3.In the form of their heavy-metal complexes, the dyes are suitable in particular for dyeing leather. These dyes are deeply colored, cover well, have good substantivity and build-up while simultaneously having good fastness properties.Type: GrantFiled: November 12, 1982Date of Patent: November 25, 1986Assignee: Ciba-Geigy CorporationInventor: Alois Puntener
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Patent number: 4623720Abstract: 1:1 and 1:2 metal complexes comprising the unit of the formula ##STR1## wherein A and B, independently, are radicals of diazo or coupling components, with the proviso that when one of A and B is a radical of a diazo component, the other is a radical of a coupling component,T is --SO.sub.2 N(R.sub.1)-- or --N(R.sub.1)SO.sub.2 --, wherein R.sub.1 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkyl substituted by phenyl or carboxy or C.sub.2-4 alkyl substituted in the .beta.--, .gamma.-- or .delta.--position by phenoxy, C.sub.1-4 alkyl, chloro or hydroxy, with the proviso that T is --N(R.sub.1)SO.sub.2 -- when A is the radical of a diazo component and T is --SO.sub.2 N(R.sub.Type: GrantFiled: June 4, 1981Date of Patent: November 18, 1986Assignee: Sandoz Ltd.Inventor: Herbert Holliger
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Patent number: 4617382Abstract: The present invention relates to novel chromium complex dyes of the formula ##STR1## wherein Z is hydrogen, chloro, bromo, nitro, lower alkyl or acylamino;L is H.sub.Type: GrantFiled: April 13, 1983Date of Patent: October 14, 1986Assignee: Ciba-Geigy CorporationInventors: Gerhard Back, Fabio Beffa, Arthur Buhler
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Patent number: 4599402Abstract: The novel compounds of the general formula I ##STR1## where A is a radical of a coupling or diazo component which, if necessary after conversion, is capable of complex formation, Ar is an unsubstituted or substituted aromatic or heterocyclic radical, D is a radical of a diazo component and Me is a Co.sup.2+, Cu.sup.2+, Zn.sup.2+, Mn.sup.2+ or Ni.sup.2+ ion, and the ring B can be further substituted, are very useful for dyeing cellulose fibers, polyesters and blends of cellulose fibers and polyesters.The present dyes are lightfast and fast to washing and to solvents.Type: GrantFiled: October 12, 1984Date of Patent: July 8, 1986Assignee: BASF AktiengesellschaftInventors: Johannes Dehnert, Werner Junemann
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Patent number: 4560747Abstract: A process for producing granulates of water-soluble dyes by means of fluidized bed granulation, wherein there is added a granulating auxiliary having a softening point or softening range between 30.degree. and 150.degree. C. and consisting of(a) at least one compound of the formula IA--(CH.sub.2 CH.sub.2 O).sub.n --H (I)in which A is the group R--O-- or ##STR1## wherein R is an aliphatic or alicyclic hydrocarbon radical having 8 to 22 carbon atoms, R' is an aliphatic hydrocarbon radical having 8 to 22 carbon atoms, and n is 10 to 200, preferably 20 to 150, or(b) a mixture of a compound of the formula II ##STR2## in which m is 50 to 500, and x is 3 to 5, with a compound of the formula IIIR.sub.1 --NH--CO--NH--R.sub.1 (III),in which each R.sub.1 independently of the other is hydrogen or methyl, or(c) a mixture of a compound of the formula I with at least one compound of the formula II or III.Type: GrantFiled: October 20, 1980Date of Patent: December 24, 1985Assignee: Ciba Geigy CorporationInventors: Beat Bruttel, Hansjorg Schneider, Werner H. Dorfel
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Patent number: 4550158Abstract: Metal-free azo compounds of the formula ##STR1## wherein Ra is an aromatic group or an active methylene coupling component radical as defined in the specification,R.sub.t is an arylazo group or a group of the formula -Y-Z,whereinY is a direct bond or a bridging radical, andZ is a basic amino or quaternary ammonium group, ##STR2## wherein each of the variables is as defined above or below, X is a direct bond or a bridging radical,x is hydrogen, hydroxy C.sub.1-4 alkyl, C.sub.1-4 alkoxy, amino or carboxy,ring B is further unsubstituted or further substituted,d is 0, 1 or 2, andn is 0 or 1,with the provisos that (i) the compounds contain an average of at least 1.3 basic water-solubilizing groups, and (ii) the compounds are free of sulfo groups,and 1:1 and 1:2 metal complexes thereof,which metal-free compounds and metal complexes are useful as dyes for leather and paper.Type: GrantFiled: August 18, 1982Date of Patent: October 29, 1985Assignee: Sandoz Ltd.Inventors: Paul Doswald, Emil Moriconi, Helmut Moser, Horst Schmid
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Patent number: 4537955Abstract: An unsymmetrical 1:2 chromium complex of a monoazo dyestuff and a disazo dyestuff which is non-fiber reactive and is free of sulfonamido and amino groups and which, in the form of the free acid has the formula: ##STR1## wherein A' is the radical of a 1-hydroxy-2-aminobenzene which is monosubstituted or disubstituted by chlorine, nitro, or sulfo, B' is a naphth-2-ol, resorcinol, p-(C.sub.1 -C.sub.6 -alkyl)-phenol, 1-phenol-3-methylpyrazol-5-one or acetoacetanilide radical, and the phenol group in the last two mentioned compounds can be substituted by C.sub.1 -C.sub.4 -alkyl C.sub.1 -C.sub.4 -alkoxy, chlorine or sulfo, K' is an unsubstituted or sulfo-substituted naphth-1-ol or naphth-2-ol radical, phenol which is substituted in the p-positioned by C.sub.1 -C.sub.6 -alkyl, an unsubstituted or sulfo-substituted 2-naphthylanime, and 1-phenol-3-methylpyrazol-5-one or an acetoactanilide radical, and the phenol group in the last two mentioned compounds can be substituted by C.sub.1 -C.sub.Type: GrantFiled: March 1, 1983Date of Patent: August 27, 1985Assignee: BASF AktiengesellschaftInventors: Klaus Grychtol, Hans Baumann
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Patent number: 4481141Abstract: Photographic elements, diffusion transfer assemblages, coordination complexes and processes are described which employ a novel nondiffusible compound having a releasable yellow dye moiety or precursor thereof, the compound having the formula: ##STR1## wherein: (a) X represents the atoms necessary to complete a 5- or 6-membered aromatic heterocyclic fused ring;(b) Z represents alkyl, substituted alkyl, aryl or substituted aryl;(c) R represents CN or J-L;(d) J represents a bivalent ##STR2## (e) L represents alkyl, substituted alkyl, aryl, substituted aryl, or can be taken together with Z to complete a carbonyl-containing 5- or 6-membered heterocyclic or carbocyclic ring;(f) Z.sup.Type: GrantFiled: April 14, 1983Date of Patent: November 6, 1984Assignee: Eastman Kodak CompanyInventor: Steven Evans