At Least Three Azo Groups Attached Indirectly To Each Other By Nonionic Bonding Patents (Class 534/685)
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Patent number: 7597721Abstract: The present invention relates to a process for producing storage-stable concentrated aqueous dye preparations of anionic dyes, to the dye preparations as such, blends/shadings with further anionic dyes and to their use, especially for printing and dyeing fiber materials.Type: GrantFiled: December 2, 2004Date of Patent: October 6, 2009Assignee: Clariant Finance (BVI) LimitedInventor: Friedrich Lehr
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Patent number: 7108897Abstract: This invention relates to a polyvinyl alcohol type polarizing film or plate which comprises a water-soluble dye having the formula (1) in a free acid form or a copper complex salt thereof.Type: GrantFiled: July 26, 2004Date of Patent: September 19, 2006Assignee: Nippon Kayaku Kabushiki KaishaInventors: Shoji Oiso, Kumiko Ishii, Yoshitaka Kajiwara, Toru Tabei
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Patent number: 6153734Abstract: Oligomeric azo dyes having an alternating construction made up of tetrazo components and coupling components, containing in the molecule at least 2 units of the structure I------[D--------K]------ (I)where D and K are as defined in the specification, are prepared and used alone or in mixtures for dyeing and printing natural or synthetic substrates.Type: GrantFiled: November 1, 1999Date of Patent: November 28, 2000Assignee: BASF AktiengesellschaftInventors: Gunter-Rudolf Schroder, Torsten Freund, Udo Mayer, Karl-Heinz Etzbach
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Patent number: 6114512Abstract: Oligomeric azo dyes having an alternating construction made up of diazo components and coupling components, containing in the molecule at least 3 units of the structure I--[D--K]-- (I)where D is a tetrazo component of the formula II ##STR1## where x is a direct bond, oxygen, sulfur or a bridge member of the formula --NHCO--, --NHCONH--, --CO--, --NHSO.sub.2 --, --SO.sub.2 NHSO.sub.2 --, --SO.sub.2 --, --SO.sub.2 --NH--A--NH--SO.sub.2 --, -NAlk-CO-, -NAlk-CO-NAlk-, -NAlk-CO--NH--, -NAlk-SO.sub.2 --, --SO.sub.2 -NAlk-SO.sub.2 --, --SO.sub.2 -NAlk-A-NAlk-SO.sub.2 --, --SO.sub.2 -NAlk-A-NH--SO.sub.2 --, --CH.dbd.CH--, --CH.sub.2 CH.sub.2 --, --C(CH.sub.3).sub.2 --, --CH.sub.2 -- or --NH--,R.sup.1 and R.sup.2 are each independently of the other hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkanoyl, cyano, carboxyl, hydroxysulfonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, hydroxyl, carbamoyl, mono- or di-(C.sub.1 -C.sub.4)-alkyl-carbamoyl, sulfamoyl, mono- or di-(C.sub.1 -C.sub.Type: GrantFiled: September 17, 1999Date of Patent: September 5, 2000Assignee: BASF AktiengesellschaftInventors: Gunter-Rudolf Schroder, Torsten Freund, Udo Mayer, Karl-Heinz Etzbach
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Patent number: 6028180Abstract: An ink comprising water, a water-dissipatable polymer and one or more dyes having a benzene ring carrying a hydroxy group at each of the 1-, 3- and 5-positions and an azo group at each of the 2-, 4- and 6-positions or a tautomer thereof.Also claimed are certain dyes, compositions printer cartridges and ink jet printers.Type: GrantFiled: March 18, 1999Date of Patent: February 22, 2000Assignee: Zeneca LimitedInventors: Andrew Paul Shawcross, Gavin Wright, Barry Huston Meyrick, Mark Holbrook
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Patent number: 5700296Abstract: An azo compound of the following formulae (I) or (II): ##STR1## wherein Q.sub.1 represents a phenyl group or a naphthyl group, Q.sub.2 represents a phenyl group; R represents hydroxy group; R.sub.1 and R.sub.2 each independently represent a hydrogen atom, a hydroxy group, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group or a halogen atom; R.sub.3 and R.sub.4 each independently represent a hydrogen atom, a hydroxy group, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group or a substituted amino group; and X represents --NH--, --NHCO-- or --N.dbd.N--; or a salt thereof;and a polarizing film containing the same.Type: GrantFiled: February 20, 1996Date of Patent: December 23, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Kazuya Ogino, Kaneo Yokoyama, Narutoshi Hayashi, Takashi Omura, Setsuko Yamamoto
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Patent number: 5659020Abstract: A tetrakisazo compound of the formulae: ##STR1## wherein Q.sup.1 represents a phenyl or naphthyl group, Q.sup.2 represents a phenyl which is substituted by at least one substituent selected from a hydroxy group and an amino group, and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each independently represents a hydrogen atom, a hydroxy group, a lower alkyl group, a lower alkoxy group or a substituted or unsubstituted amino group, or a salt thereof, and a polarizing film which comprises the tetrakisazo compound or a salt thereof and which may further comprise other organic dyes.Type: GrantFiled: September 13, 1995Date of Patent: August 19, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Kazuya Ogino, Kaneo Yokoyama, Narutoshi Hayashi, Takashi Omura
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Patent number: 5536819Abstract: A trisazo compound represented by the following formula (I) in the free acid form: ##STR1## wherein Q is an phenyl or naphthyl group both of which may be unsubstituted or substituted; one of the A and B is hydroxy group and the other is amino group; K is 1 or 2; and one of m and n is 1 and the other is 0; a method for dyeing fiber materials, paper or leather by using the trisazo compounds and an ink containing the trisazo compounds, and the trisazo compound is excellent in solubility, and good in storage stability and free from clogging of nozzle caused by deposition. The ink using the trisazo compound gives a deep black-colored image excellent in clarity, water-durability and durability to light.Type: GrantFiled: May 20, 1994Date of Patent: July 16, 1996Assignee: Sumitomo Chemical Company, LimitedInventors: Yuriko Tamura, Kazuya Ogino, Mahito Fujita, Takashi Omura, Hideo Kawashita, Koji Aburada
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Patent number: 5530105Abstract: A tetrakisazo compound represented by the following formula (1) in the free acid form: ##STR1## wherein Q.sub.1 and Q.sub.2 independently represent phenylene or naphthylene group which may be optionally substituted, R.sub.4, R.sub.5 and R.sub.6 independently represent a hydrogen atom, a halogen atom, a hydroxy group, a sulfonic acid group or an amino, alkyl, alkoxy, carbamoyl or sulfamoyl group which may be optionally substituted, m is 0 or 1 and n is 1 or 2, and an ink which comprises the tetrakisazo compound. The ink exhibit excellent properties for ink jet printing.Type: GrantFiled: September 27, 1994Date of Patent: June 25, 1996Assignee: Sumitomo Chemical Company, LimitedInventors: Satoshi Yamazaki, Hideo Kawashita, Koji Aburada, Kazuya Ogino, Yuriko Tamura, Takashi Omura
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Patent number: 5488101Abstract: Herein is provided a trisazo compound represented by formula (I) in the free acid form: ##STR1## wherein Q.sub.1 is an unsubstituted or substituted phenylene or naphthylene group, Q.sub.2 is an unsubstituted or substituted phenyl or naphthyl group, Z is --SO.sub.2 CH.sub.2 CH.sub.2 OH or --SO.sub.2 CH.sub.2 CH.sub.2 SO.sub.3 H group, and L is 0 or 1. The trisazo compound provided herein is excellent in solubility and gives deep colored dyed product or image when used in dyeing or printing, so that it is useful as a dye and an ink. Herein are also provided a method for dyeing fiber materials, paper or leather by using said trisazo compound, and an ink containing said trisazo compound.Type: GrantFiled: June 5, 1992Date of Patent: January 30, 1996Assignee: Sumitomo Chemical Company, LimitedInventors: Kazuya Ogino, Kingo Akahori, Naoki Harada, Yutaka Kayane, Hideo Kawashita, Mituhiro Ohta
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Patent number: 5486601Abstract: Disclosed is a trisazo dye represented by the formula: ##STR1## wherein R.sup.1 and R.sup.2 independently represent a substituted amino group which is substituted with hydrogen, a hydroxyl group, a carboxyl group, an amino group, an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group or an acyl group, or an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms; and R.sup.3 is hydrogen, an alkyl or alkoxy group having 1 to 6 carbon atoms; provided that R.sup.1 and R.sup.2 are not amino groups or substituted amino groups simultaneously.A process for producing the trisazo dye and an aqueous ink composition containing the trisazo dye are also disclosed.Type: GrantFiled: September 28, 1994Date of Patent: January 23, 1996Assignee: Orient Chemical Industries, Ltd.Inventors: Tatsuya Yagyu, Takashi Ono
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Patent number: 5470959Type: GrantFiled: January 24, 1994Date of Patent: November 28, 1995Assignee: BASF AktiengesellschaftInventors: Gunther Lamm, Udo Mayer, Helmut Reichelt, Georg Zeidler
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Patent number: 5340929Abstract: The present invention provides a trisazo dye represented by the formula: ##STR1## wherein B is a substituted or non-substituted phenyl group, A is a phenyl group substituted with at least one substituent selected from the group consisting of an amino group, a substituted amino and a hydroxyl group, R is a substituted or non-substituted phenyl group or an alkyl group having 1 to 8 carbon atoms, and M is hydrogen, alkali metal, aliphatic alkyl ammonium or alkanol ammonium. An aqueous ink composition and a process for the producing a concentrated solution containing the trisazo dye are also disclosed.Type: GrantFiled: February 12, 1993Date of Patent: August 23, 1994Assignee: Orient Chemical Industries, Ltd.Inventors: Takashi Ono, Tatsuya Yagyu, Yoshihiro Sawatari, Masaki Yonezawa
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Patent number: 5336763Abstract: The present invention provides a trisazo dye represented by the formula: ##STR1## [wherein A is a phenyl group substituted with at least one substituent selected from the group consisting of an amino group, a substituted amino group and a hydroxyl group, B is a substituted or non-substituted phenyl group, X is a group of the formula: ##STR2## Q is a group of the formula: ##STR3## (wherein n is 1 or 2), and M is hydrogen, alkali metal, aliphatic alkyl ammonium or alkanol ammonium]. An aqueous ink composition and a process for the producing a concentrated solution containing the trisazo dye are also disclosed.Type: GrantFiled: February 12, 1993Date of Patent: August 9, 1994Assignee: Orient Chemical Industries, Ltd.Inventors: Takashi Ono, Tatsuya Yagyu, Yoshihiro Sawatari, Masaki Yonezawa
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Patent number: 5320647Abstract: Fluent dye preparations useful for dyeing leather or wool containa) at least 15% of the weight of the dye preparation of one or more polyazo dyes in salt form which have one or more hydroxysulfonyl and/or carboxyl groups and may be present in the form of a 1:1 or 1:2 metal complex,b) from 2 to 15% of the weight of the dye preparation of a surfactant, andc) water.Type: GrantFiled: August 14, 1992Date of Patent: June 14, 1994Assignee: BASF AktiengesellschaftInventors: Georg Henning, Georg Zeidler, Ortwin Schaffer
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Patent number: 5270455Abstract: A metal complex suitable as dyes for the dyeing of a wide range of textile and non-textile materials, particularly leather and fur, said metal complex of a compound of the formula ##STR1## in which D and D.sub.1, independently of one another, are each the radical of a diazo component of the benzene or naphthalene series and M is a phenylene radical which may be further substituted.Type: GrantFiled: July 27, 1992Date of Patent: December 14, 1993Assignee: Ciba-Geigy CorporationInventor: Ulrich Schlesinger
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Patent number: 5171848Abstract: Black compounds of Formula (1) having enhanced solubility in polar organic liquids which are useful as ink colorants in conventional and hot melt ink-jet printing and automatic identification, as black colorants for toners and thermal wax transfer sheets and as charge control agents for electrophotographic toners; ##STR1## wherein R is H, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, aryl, C.sub.4-8 cycloalkyl, --CN, --NO.sub.2, halogen, --COOR.sup.1, --OH, --SH or --SO.sub.3 A;R.sup.1 is A, C.sub.1-4 -alkyl or aryl;R.sup.2 is --NH.sub.2, --OH or --SO.sub.3 A;R.sup.3 is --NH.sub.2 or --OH;R.sup.4 is --NH.sub.2, --OH, --SO.sub.3 A or H; andA is NQ.sub.4 in which at least one Q is a branched chain fatty C.sub.6-20 -aliphatic group.Type: GrantFiled: March 30, 1992Date of Patent: December 15, 1992Assignee: Imperial Chemical Industries PLCInventors: David Greenwood, Peter Gregory, John E. Presgrave
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Patent number: 5127946Abstract: Provided is an ink containing a recording agent and a liquid medium for dissolution or dispersion thereof, said ink comprising, as the recording agent, a compound represented by the general formula (A) ##STR1## where n is 0 or 1; R.sub.1, R.sub.2, and R.sub.3 are respectively a substituent selected from the group consisting of hydrogen, methyl, methoxy, hydroxy, amino, acetylamino, and sulfonic acid; and M is an alkali metal, ammonium, or an organic ammonium.Type: GrantFiled: January 23, 1991Date of Patent: July 7, 1992Assignee: Canon Kabushiki KaishaInventors: Tsuyoshi Eida, Takao Yamamoto, Mayumi Yamamoto
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Patent number: 5116955Abstract: There is disclosed a process for coupling one or more different diazo components with resorcinol on an industrial scale. The process comprises adjusting and stabilizing the coupling pH of the resorcinol prior to the reaction with the aid of a buffer system and keeping it constant during the coupling reaction or reactions by controlling the ratio of flow of the streams of the diazo component or components and the base. The process makes it possible to prepare mono- and polyazo dyes in excellent uniform quality and yield.Type: GrantFiled: September 25, 1990Date of Patent: May 26, 1992Assignee: Ciba-Geigy CorporationInventors: Horst Langfeld, Roland Minges
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Patent number: 5104979Abstract: Polyazo dyes useful for dyeing leather in the free form or as copper, chromium, iron, cobalt or nickel complexes have the formula ##STR1## where m is 0, 1 or 2, n is 0 or 1, p is from 1 to 2, q is from 0 to 1, and R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, X, Y and the ring A are each as defined, and may be prepared from aniline derivatives of the formula ##STR2## where m is 0, 1, or 2, n is 0 or 1, and X, R.sup.1, R.sub.2 and R.sup.3 are each as defined.Type: GrantFiled: July 31, 1990Date of Patent: April 14, 1992Assignee: BASF AktiengesellschaftInventors: Guenter Hansen, Georg Zeidler, Ortwin Schaffer
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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: 4988804Abstract: Polyazo dyes obtainable by(a) diazotizing 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid and coupling onto a compound of the formula ##STR1## (b) coupling a diazotized compound of the formula ##STR2## onto the monoazo dye thus obtained, (c) coupling a diazotized compound of the formula ##STR3## onto the product obtained as per (b), and (d) if desired metallizing the product obtained as per (c), the symbols in the formulae being as defined in claim 1, are suitable for dyeing a wide range of textile and nontextile materials, in particular leather.Type: GrantFiled: October 31, 1988Date of Patent: January 29, 1991Assignee: Ciba-Geigy CorporationInventor: Horst Langfeld
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Patent number: 4874848Abstract: Dyes which are 1:2-chromium complexes, containing one azo dye or azomethine dye and one disazo dye or trisazo dye. The dyes are suitable for dyeing wool, synthetic polyamides and leather.Type: GrantFiled: June 4, 1986Date of Patent: October 17, 1989Assignee: Ciba-Geigy CorporationInventors: Gerhard Back, Fabio Beffa
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Patent number: 4758659Abstract: A hexakisazo dye suitable for dyeing cellulose, natural or synthetic polyamide meterials, leather, represented by the formula ##STR1## wherein X is --CH.dbd.CH--, --CONH--, --CRH-- (wherein R is phenyl which is unsubstituted or substituted by H or a sulfonic acid group), -SO.sub.2 -- or --O--; Y is H, CH.sub.3 OCH.sub.3, Cl or SO.sub.3 M; A.sub.1 and A.sub.2 are each ##STR2## (wherein Z.sub.1 is H, Cl, CH.sub.3, OH, OCH.sub.3, OC.sub.2 H.sub.5 or SO.sub.3 M, and Z.sub.2 is H, CH.sub.3, NO.sub.2 or COOM); B.sub.1 and B.sub.2 are each ##STR3## (wherein Z.sub.3 is H, OH, NH.sub.2 Cl or COOM, Z.sub.4 is H, Cl, CH.sub.3, OH OCH.sub.3, NH.sub.2, COOM or SO.sub.3 M, and Z.sub.5 is H, C.sub.1 -C.sub.4 alkyl or OH); M is H, Na, K, Li or NH.sub.4 ; f is 0 or 1; m is 0, 1 or 2; and n is 0, 1 or 2.Type: GrantFiled: July 29, 1986Date of Patent: July 19, 1988Assignee: Orient Chemical Industries, Ltd.Inventors: Hisashi Senshu, Sadahiko Matsubara, Tamotsu Naito
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Patent number: 4701525Abstract: Compounds of the formula(B--L.sub.m --A--L'--B'.sub.n, (1)in which A is the radical of a bisazo or trisazo dye, L and L' are organic radicals and B and B' are cyclic organic radicals and at least one of the radicals B and B' has spectral absorption in the UV region and one of the radicals B and B' is different from 2,4-dihydroxyphenyl, m is 1 or 2 and n is 0, 1 or 2.The compounds are suitable for use as image dyes in photographic silver dye bleach materials.Type: GrantFiled: June 2, 1986Date of Patent: October 20, 1987Assignee: Ciba-Geigy AGInventors: Thomas-Markus Rohr, Jakob Kuhn
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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: 4587292Abstract: 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,R is ##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: May 6, 1986Assignee: Sandoz Ltd.Inventors: Paul Doswald, Emil Moriconi, Helmut Moser, Horst Schmid
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Patent number: 4491543Abstract: The present invention discloses substituted phenyl di and trisazo dyes free of reactive groups having two or three sulfonic acid groups, of the general formula: ##STR1## wherein D.sup.1 is ##STR2## Z is hydrogen or D.sup.4 --N.dbd.N--; D.sup.2 is phenyl substituted by hydroxyl, hydroxysulfonyl, chlorine or nitro, or is naphthyl substituted by hydroxy, hydroxysulfonyl or nitro, X, independently of one another, are hydroxyl or amino, D.sup.3 is phenyl which is substituted by hydroxysulfonyl, chlorine, bromine, methyl, methoxy, ethoxy, nitro, phenylamino, sulfophenylamino or nitrosulfophenylamino, or is naphthyl which is substituted by hydroxysulfonyl; D.sup.4 is phenyl which is unsubstituted or substituted by methyl, ethyl, methoxy, ethoxy, chlorine, bromine, nitro, sulfamoyl or hydroxysulfonyl, or is naphthyl which is substituted by hydroxysulfonyl; and R.sup.Type: GrantFiled: May 21, 1982Date of Patent: January 1, 1985Assignee: BASF AktiengesellschaftInventors: Udo Bergmann, Guenter Hansen, Dietrich Lach, Michael Thomas, Georg Zeidler