At Least Three Azo Groups Attached Indirectly To Each Other By Nonionic Bonding Patents (Class 534/685)
  • Patent number: 7597721
    Abstract: 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: Grant
    Filed: December 2, 2004
    Date of Patent: October 6, 2009
    Assignee: Clariant Finance (BVI) Limited
    Inventor: Friedrich Lehr
  • Patent number: 7108897
    Abstract: 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: Grant
    Filed: July 26, 2004
    Date of Patent: September 19, 2006
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Shoji Oiso, Kumiko Ishii, Yoshitaka Kajiwara, Toru Tabei
  • Patent number: 6153734
    Abstract: 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: Grant
    Filed: November 1, 1999
    Date of Patent: November 28, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Gunter-Rudolf Schroder, Torsten Freund, Udo Mayer, Karl-Heinz Etzbach
  • Patent number: 6114512
    Abstract: 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: Grant
    Filed: September 17, 1999
    Date of Patent: September 5, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Gunter-Rudolf Schroder, Torsten Freund, Udo Mayer, Karl-Heinz Etzbach
  • Patent number: 6028180
    Abstract: 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: Grant
    Filed: March 18, 1999
    Date of Patent: February 22, 2000
    Assignee: Zeneca Limited
    Inventors: Andrew Paul Shawcross, Gavin Wright, Barry Huston Meyrick, Mark Holbrook
  • Patent number: 5700296
    Abstract: 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: Grant
    Filed: February 20, 1996
    Date of Patent: December 23, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazuya Ogino, Kaneo Yokoyama, Narutoshi Hayashi, Takashi Omura, Setsuko Yamamoto
  • Patent number: 5659020
    Abstract: 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: Grant
    Filed: September 13, 1995
    Date of Patent: August 19, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazuya Ogino, Kaneo Yokoyama, Narutoshi Hayashi, Takashi Omura
  • Patent number: 5536819
    Abstract: 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: Grant
    Filed: May 20, 1994
    Date of Patent: July 16, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yuriko Tamura, Kazuya Ogino, Mahito Fujita, Takashi Omura, Hideo Kawashita, Koji Aburada
  • Patent number: 5530105
    Abstract: 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: Grant
    Filed: September 27, 1994
    Date of Patent: June 25, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Satoshi Yamazaki, Hideo Kawashita, Koji Aburada, Kazuya Ogino, Yuriko Tamura, Takashi Omura
  • Patent number: 5488101
    Abstract: 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: Grant
    Filed: June 5, 1992
    Date of Patent: January 30, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazuya Ogino, Kingo Akahori, Naoki Harada, Yutaka Kayane, Hideo Kawashita, Mituhiro Ohta
  • Patent number: 5486601
    Abstract: 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: Grant
    Filed: September 28, 1994
    Date of Patent: January 23, 1996
    Assignee: Orient Chemical Industries, Ltd.
    Inventors: Tatsuya Yagyu, Takashi Ono
  • Patent number: 5470959
    Type: Grant
    Filed: January 24, 1994
    Date of Patent: November 28, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Gunther Lamm, Udo Mayer, Helmut Reichelt, Georg Zeidler
  • Patent number: 5340929
    Abstract: 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: Grant
    Filed: February 12, 1993
    Date of Patent: August 23, 1994
    Assignee: Orient Chemical Industries, Ltd.
    Inventors: Takashi Ono, Tatsuya Yagyu, Yoshihiro Sawatari, Masaki Yonezawa
  • Patent number: 5336763
    Abstract: 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: Grant
    Filed: February 12, 1993
    Date of Patent: August 9, 1994
    Assignee: Orient Chemical Industries, Ltd.
    Inventors: Takashi Ono, Tatsuya Yagyu, Yoshihiro Sawatari, Masaki Yonezawa
  • Patent number: 5320647
    Abstract: 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: Grant
    Filed: August 14, 1992
    Date of Patent: June 14, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Georg Henning, Georg Zeidler, Ortwin Schaffer
  • Patent number: 5270455
    Abstract: A metal complex suitable as dyes for the dyeing of a wide range of textile and non-textile materials, particularly leather and fur, said metal complex of a compound of the formula ##STR1## in which D and D.sub.1, independently of one another, are each the radical of a diazo component of the benzene or naphthalene series and M is a phenylene radical which may be further substituted.
    Type: Grant
    Filed: July 27, 1992
    Date of Patent: December 14, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Ulrich Schlesinger
  • Patent number: 5171848
    Abstract: 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: Grant
    Filed: March 30, 1992
    Date of Patent: December 15, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: David Greenwood, Peter Gregory, John E. Presgrave
  • Patent number: 5127946
    Abstract: 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: Grant
    Filed: January 23, 1991
    Date of Patent: July 7, 1992
    Assignee: Canon Kabushiki Kaisha
    Inventors: Tsuyoshi Eida, Takao Yamamoto, Mayumi Yamamoto
  • Patent number: 5116955
    Abstract: 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: Grant
    Filed: September 25, 1990
    Date of Patent: May 26, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Horst Langfeld, Roland Minges
  • Patent number: 5104979
    Abstract: 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: Grant
    Filed: July 31, 1990
    Date of Patent: April 14, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Guenter Hansen, Georg Zeidler, Ortwin Schaffer
  • Patent number: 5001226
    Abstract: 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: Grant
    Filed: December 19, 1989
    Date of Patent: March 19, 1991
    Assignee: Sandoz Ltd.
    Inventors: Helmut A. Moser, Roland Wald
  • Patent number: 4996302
    Abstract: A process for the preparation of polyazo dyes is described which comprises(a) diazotizing a compound of the formula ##STR1## and coupling the product onto a compound of the formula ##STR2## (b) diazotizing a compound of the formula ##STR3## and coupling the product onto the product obtained according to (a); (c) diazotizing a compound of the formula ##STR4## and coupling the product onto the product obtained according to (b); (d) if desired, coupling of a further diazotized compound of the formula (3) onto the product obtained according to (c); and(e) if desired, metallizing the product obtained according to (c) or (d); and in which the symbols are as defined in claim 1. The polyazo dyes obtainable by the process are suitable for dyeing a wide range of textile and non-textile materials and, in particular, for dyeing leather.
    Type: Grant
    Filed: December 7, 1988
    Date of Patent: February 26, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Horst Langfeld
  • Patent number: 4988804
    Abstract: 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: Grant
    Filed: October 31, 1988
    Date of Patent: January 29, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Horst Langfeld
  • Patent number: 4874848
    Abstract: 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: Grant
    Filed: June 4, 1986
    Date of Patent: October 17, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Gerhard Back, Fabio Beffa
  • Patent number: 4758659
    Abstract: 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: Grant
    Filed: July 29, 1986
    Date of Patent: July 19, 1988
    Assignee: Orient Chemical Industries, Ltd.
    Inventors: Hisashi Senshu, Sadahiko Matsubara, Tamotsu Naito
  • Patent number: 4701525
    Abstract: 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: Grant
    Filed: June 2, 1986
    Date of Patent: October 20, 1987
    Assignee: Ciba-Geigy AG
    Inventors: Thomas-Markus Rohr, Jakob Kuhn
  • Patent number: 4665162
    Abstract: 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: Grant
    Filed: June 18, 1985
    Date of Patent: May 12, 1987
    Assignee: Sandoz Ltd.
    Inventors: Paul Doswald, Emil Moriconi, Helmut Moser, Horst Schmid
  • Patent number: 4587292
    Abstract: 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: Grant
    Filed: August 18, 1982
    Date of Patent: May 6, 1986
    Assignee: Sandoz Ltd.
    Inventors: Paul Doswald, Emil Moriconi, Helmut Moser, Horst Schmid
  • Patent number: 4491543
    Abstract: 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: Grant
    Filed: May 21, 1982
    Date of Patent: January 1, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Udo Bergmann, Guenter Hansen, Dietrich Lach, Michael Thomas, Georg Zeidler