At Least Three Azo Groups Attached Indirectly To Each Other By Nonionic Bonding Patents (Class 534/796)
  • Publication number: 20140024815
    Abstract: A dendritic structure includes a core and repeating units, wherein the repeating units comprise units of the type ABxCy, wherein x is 2, 3, or 4, wherein y is 1, 2, or 3, wherein C is selected from the group consisting of azides and alkynes, and wherein every repeating unit is bound to at least one other unit with at least one bond selected from the group consisting of the group consisting of an ester, an amide, a thioether, an ether, a urethane, an amine, and an imine. Advantages include that a “one-pot” growth of the dendritic structure is possible. It is possible to have more functional groups in a dendritic structure. It is possible to add different functional groups simultaneously both to an inner layer and to an outer layer in a dendritic structure.
    Type: Application
    Filed: September 25, 2013
    Publication date: January 23, 2014
    Applicant: POLYMER FACTORY SWEDEN AB
    Inventors: Anders HULT, Michael MALKOCH, Per ANTONI
  • Publication number: 20130302538
    Abstract: The present invention relates to an azo compound represented by the following formula (1), [wherein, A represents a phenyl group which may have a substituent, R1 to R6 each independently represent a hydrogen atom, an alkyl group having a carbon atom number of 1 to 5, an alkoxy group having a carbon atom number of 1 to 5, a sulfo group, or an alkoxy group having a sulfo group and a carbon atom number of 1 to 5, and X represents an amino group which may have a substituent, a benzoylamino group which may have a substituent, a phenylamino group which may have a substituent, a phenylazo group which may have a substituent, or a naphthotriazole group which may have a substituent] or/and a salt thereof and to a polarizing film and a polarizing plate which contain it.
    Type: Application
    Filed: February 6, 2012
    Publication date: November 14, 2013
    Applicants: POLATECHNO CO., LTD., NIPPON KAYAKU KABUSHIKI KAISHA
    Inventors: Takahiro Higeta, Takuto Nishiguchi
  • Patent number: 8512462
    Abstract: Azo compounds represented by general formula (1) or salts thereof are provided as highly water-soluble colorants which have hues of yellow, orange, brown or red, and excellent color development properties and which, when used in various recording processes, particularly in an inkjet recording process, ensure various excellent fastnesses such as light fastness, ozone fastness, and fading balance. Ink compositions containing the colorants are also provided. In general formula (1), R1 to R8 are each independently a hydrogen atom, C1-4 alkyl, C1-4 alkoxy, or the like; and X is C1-8 alkylenediamino, xylylenediamino, or the like.
    Type: Grant
    Filed: September 21, 2010
    Date of Patent: August 20, 2013
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Takahiko Matsui, Takashi Yoshimoto, Hiroaki Ohno, Koji Hirota, Takashi Yoneda, Akira Kawaguchi
  • Patent number: 8389124
    Abstract: Disclosed is an azo compound represented by the formula (1) or (2) below, or a salt thereof. (In the formulae, A represents a substituted phenyl group or a naphthyl group having 1-3 sulfonic acid groups; X represents —N?N— or —NHCO—; R1-R4 independently represent a hydrogen atom, a lower alkyl group or a lower alkoxyl group; m represents a number of 1-3; and n represents 0 or 1.
    Type: Grant
    Filed: July 13, 2011
    Date of Patent: March 5, 2013
    Assignees: Nippon Kayaku Kabushiki Kaisha, Polatechno Co., Ltd.
    Inventors: Yuichi Sadamitsu, Hiroaki Ohno, Takahiro Higeta
  • Patent number: 8389122
    Abstract: Disclosed is an azo compound represented by the formula (1) or (2) below, or a salt thereof. (In the formulae, A represents a substituted phenyl group or a naphthyl group having 1-3 sulfonic acid groups; X represents —N?N— or —NHCO—; R1-R4 independently represent a hydrogen atom, a lower alkyl group or a lower alkoxyl group; m represents a number of 1-3; and n represents 0 or 1).
    Type: Grant
    Filed: June 12, 2007
    Date of Patent: March 5, 2013
    Assignees: Nippon Kayaku Kabushiki Kaisha, Polatechno Co., Ltd.
    Inventors: Yuichi Sadamitsu, Hiroaki Ohno, Takahiro Higeta
  • Publication number: 20120202019
    Abstract: Azo compounds represented by general formula (1) or salts thereof are provided as highly water-soluble colorants which have hues of yellow, orange, brown or red, and excellent color development properties and which, when used in various recording processes, particularly in an inkjet recording process, ensure various excellent fastnesses such as light fastness, ozone fastness, and fading balance. Ink compositions containing the colorants are also provided. In general formula (1), R1 to R8 are each independently a hydrogen atom, C1-4 alkyl, C1-4 alkoxy, or the like; and X is C1-8 alkylenediamino, xylylenediamino, or the like.
    Type: Application
    Filed: September 21, 2010
    Publication date: August 9, 2012
    Applicant: NIPPON KAYAKU KABUSHIKI KAISHA
    Inventors: Takahiko Matsui, Takashi Yoshimoto, Hiroaki Ohno, Koji Hirota, Takashi Yoneda, Akira Kawaguchi
  • Publication number: 20110267691
    Abstract: Disclosed is an azo compound represented by the formula (1) or (2) below, or a salt thereof. (In the formulae, A represents a substituted phenyl group or a naphthyl group having 1-3 sulfonic acid groups; X represents —N?N— or —NHCO—; R1-R4 independently represent a hydrogen atom, a lower alkyl group or a lower alkoxyl group; m represents a number of 1-3; and n represents 0 or 1.
    Type: Application
    Filed: July 13, 2011
    Publication date: November 3, 2011
    Applicants: POLATECHNO CO., LTD., NIPPON KAYAKU KABUSHIKI KAISHA
    Inventors: Yuichi Sadamitsu, Hiroaki Ohno, Takahiro Higeta
  • Publication number: 20110052696
    Abstract: A dendritic structure includes a core and repeating units, wherein the repeating units comprise units of the type ABxCy, wherein x is 2, 3, or 4, wherein y is 1, 2, or 3, wherein C is selected from the group consisting of azides and alkynes, and wherein every repeating unit is bound to at least one other unit with at least one bond selected from the group consisting of the group consisting of an ester, an amide, a thioether, an ether, a urethane, an amine, and an imine. Advantages include that a “one-pot” growth of the dendritic structure is possible. It is possible to have more functional groups in a dendritic structure. It is possible to add different functional groups simultaneously both to an inner layer and to an outer layer in a dendritic structure.
    Type: Application
    Filed: May 6, 2009
    Publication date: March 3, 2011
    Applicant: POLYMER FACTORY SWEDEN AB
    Inventors: Anders Hult, Michael Malkoch, Per Antoni
  • Publication number: 20090174942
    Abstract: Disclosed is an azo compound represented by the formula (1) or (2) below, or a salt thereof. (In the formulae, A represents a substituted phenyl group or a naphthyl group having 1-3 sulfonic acid groups; X represents —N?N— or —NHCO—; R1-R4 independently represent a hydrogen atom, a lower alkyl group or a lower alkoxyl group; m represents a number of 1-3; and n represents 0 or 1.
    Type: Application
    Filed: June 12, 2007
    Publication date: July 9, 2009
    Inventors: Yuichi Sadamitsu, Hiroaki Ohno, Takahiro Higeta
  • Publication number: 20080196180
    Abstract: The present invention provides 6-azo-5,5?-dihydroxy-7,7?-disulfo-2,2?-dinaphthylamine derivatives, their use as dyes, dyed paper and formulations comprising them.
    Type: Application
    Filed: January 11, 2006
    Publication date: August 21, 2008
    Inventor: Holger Lautenbach
  • Patent number: 7371831
    Abstract: Compounds of formula (I) wherein all substituents have the meanings as defined in the Specification, their production and their use.
    Type: Grant
    Filed: February 11, 2002
    Date of Patent: May 13, 2008
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Martin Oberholzer, Jürgen Geiwiz
  • Patent number: 6451988
    Abstract: Novel naphthol derivatives, and various azo compounds and metal complexes prepared by using the derivatives are provided. The instant invention provides naphthol derivatives represented by general formula (1); wherein at least one of Y1 and Y2 is a group represented by formula (2); wherein X1 is —O—, —S— or —NH—; and Z is an optionally substituted aromatic group or heterocyclic group having conjugated double bonds, and salts thereof; mono-, bis-, and trisazo compounds prepared from the derivatives; and metal complexes containing the derivatives as the ligand.
    Type: Grant
    Filed: January 16, 2002
    Date of Patent: September 17, 2002
    Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo
    Inventors: Ryuzo Ueno, Masaya Kitayama, Kenji Minami, Hiroyuki Wakamori
  • Patent number: 6140477
    Abstract: A polyazo compound capable of effectively absorbing near-infrared rays, which can be produced from readily available raw materials is provided, which comprises at least one --OH group or at least one group derived from --OH group at p-position of the azo group in the molecule of the polyazo compound. This compound can be produced by diazotizing a substituted or nonsubstituted aromatic monocyclic or polycyclic compound or heterocyclic compound, each having a diazotizable primary amino group, and successively coupling the resulting diazo component with an azo component having a diazotizable primary amino group, the last azo component being such that --OH group or a group derived from --OH group be present at p-position to the azo group resulting from the azo component.
    Type: Grant
    Filed: March 23, 1999
    Date of Patent: October 31, 2000
    Assignee: Hakkol Chemical Co., Ltd.
    Inventors: Shigekazu Matsumoto, Takao Yanagisawa, Shigehiro Matsumoto, Kunio Shimabukuro
  • Patent number: 6068687
    Abstract: Azo dyes of formula (4) ##STR1## wherein A, R.sub.4, M and m are as defined in the specification, are excellent dyes for dyeing and printing of cellulose containing materials and especially for the preparation of inks for ink jet printing.
    Type: Grant
    Filed: November 19, 1998
    Date of Patent: May 30, 2000
    Assignee: Ilford Imaging Switzerland GmbH
    Inventors: Kurt Baettig, Gerald Jan
  • Patent number: 6013775
    Abstract: Polyazo dyes of the formula I ##STR1## where one of the two radicals X.sup.1 and X.sup.2 is hydroxyl and the other is amino,p and q are each independently of the other 0 or 1,D.sup.1 and D.sup.2 are each independently of the other a radical of the formula ##STR2## and B is a bridge member are prepared using novel sulfonamide intermediates and are useful as dyes for dyeing natural or synthetic substrates.
    Type: Grant
    Filed: October 28, 1997
    Date of Patent: January 11, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Gunther Lamm, Matthias Wiesenfeldt
  • Patent number: 6011141
    Abstract: Polyazo dyes of the formula ##STR1## where n, Y.sup.1, Y.sup.2, Y.sup.3, Y.sup.4, X, R.sup.1, R.sup.2 and R.sup.3 are each as defined in more detail in the description are useful for dyeing natural or synthetic substrates.
    Type: Grant
    Filed: June 19, 1998
    Date of Patent: January 4, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Gunther Lamm, Helmut Reichelt, Matthias Wiesenfeldt
  • Patent number: 5844100
    Abstract: There is described novel azo dyes of formula (4) with high water solubility for use in aqueous inks, particularly for ink jet recording, which provide images having high water, smudge and light resistance ##STR1## wherein n, m are each independently 2 to 6;R is hydrogen or an aliphatic radical having from 1 to 6 atoms;M is hydrogen, a metal atom, preferentially an alkali metal, an ammonium or ammonium substituted with alkyl, alkoxyalkyl or hydroxyalkyl each having 1 to 12 C atomsandF represents a mono-azo or a poly-azo dye residue.
    Type: Grant
    Filed: September 11, 1997
    Date of Patent: December 1, 1998
    Assignee: Ilford Imaging Switzerland GmbH
    Inventor: Kurt Baettig
  • Patent number: 5786459
    Abstract: Compounds of the formula (I) ##STR1## have been found which are suitable for dyeing and printing hydroxyl- and/or amido-containing substrates, in particular for printing paper by the ink-jet method.
    Type: Grant
    Filed: July 5, 1996
    Date of Patent: July 28, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Frank-Michael Stohr, Peter Wild
  • Patent number: 5773593
    Abstract: A bisazo compound of the Formula (1) and salts thereof: ##STR1## wherein Ar.sup.1, Ar.sup.2, each J, each X, L, R.sup.1 and R.sup.2 are as defined in the description, provided that L comprises the residue ##STR2## and/or L.sup.1 is--NH--A--NR.sup.9 R.sup.10wherein L.sup.1, A, R.sup.9 and R.sup.10 are as defined in the description, the compounds of Formula (1) being free from fiber-reactive groups and any carboxyl substituents present in the compounds being attached in the form of one or more residue of the following formulae: ##STR3## Also disclosed are ink compositions comprising the above compound; a process for printing substrates with the ink compositions using an ink-jet printer; paper, project slides and textile materials printed with the ink compositions; and a process for coloration of textile materials with the ink compositions.
    Type: Grant
    Filed: December 18, 1996
    Date of Patent: June 30, 1998
    Assignee: Zeneca Limited
    Inventors: Peter Gregory, Ronald Wynford Kenyon, Paul Wight
  • Patent number: 5756692
    Abstract: A bisazo compound of the Formula (1) and salts thereof: ##STR1## wherein the variables are as defined in the specification, the compounds of Formula (1) being free from fibre-reactive groups and any carboxyl substituents present in the compounds being attached in the form of one or more residue of the following formulae: ##STR2## Also claimed are ink compositions comprising the above compound; a precess for printing substrates with the ink compositions using an ink-jet printer; paper, project slides and textile materials printed with the ink compositions; and a process for coloration of textile materials with the ink compositions.
    Type: Grant
    Filed: December 18, 1996
    Date of Patent: May 26, 1998
    Assignee: Zeneca Limited
    Inventors: Peter Gregory, Ronald Wynford Kenyon, Paul Wight
  • Patent number: 5721344
    Abstract: There is described novel azo dyes of formula (4) with high water solubility for use in aqueous inks, particularly for ink jet recording, which provide images having high water, smudge and light resistance ##STR1## wherein n, m are each independently 2 to 6;R is hydrogen or an aliphatic radical having from 1 to 6 atoms;M is hydrogen, a metal atom, preferentially an alkali metal, an ammonium or ammonium substituted with alkyl, alkoxyalkyl or hydroxyalkyl each having 1 to 12 C atomsandF represents a mono-azo or a poly-azo dye residue.
    Type: Grant
    Filed: July 19, 1996
    Date of Patent: February 24, 1998
    Assignee: Ilford A.G.
    Inventor: Kurt Baettig
  • Patent number: 5646257
    Abstract: The new dyestuffs of the formula (I) ##STR1## wherein the substituents R and R.sup.1 and the index n have the meaning given in the description, are outstandingly suitable for dyeing and printing cellulose-containing materials, in particular for the preparation of recording liquids for ink jet recording systems.
    Type: Grant
    Filed: November 18, 1994
    Date of Patent: July 8, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karin Hassenruck, Karl-Heinz Reinhardt, Peter Wild, Klaus Wunderlich
  • Patent number: 5639864
    Abstract: Azo dyes of formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other hydrogen or unsubstituted or substituted C.sub.1 -C.sub.4 alkyl,R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are each independently of one another hydrogen, halogen, sulfo, carbamoyl, carboxy, unsubstituted or hydroxy-substituted C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;C.sub.2 -C.sub.4 alkanoylamino which is unsubstituted or substituted in the alkyl moiety by hydroxy or C.sub.1 -C.sub.4 alkoxy, or ureido which is unsubstituted or substituted in the amino end group by one or two C.sub.1 -C.sub.4 alkyl groups,Y.sub.1 is hydroxy, halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, amino; N-mono-C.sub.1 -C.sub.4 alkylamino or N,N-di-C.sub.1 -C.sub.4 alkylamino, each of which is unsubstituted or substituted in the alkyl moiety by hydroxy, sulfo, carboxy or C.sub.1 -C.sub.4 alkoxy; C.sub.5 -C.sub.7 cycloalkylamino which is unsubstituted or substituted in the cycloalkyl ring by C.sub.1 -C.sub.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: June 17, 1997
    Assignee: Ciba-Geigy Corporation
    Inventor: Urs Lauk
  • Patent number: 5637679
    Abstract: New azo dyestuffs of the formula (I) ##STR1## wherein n in each case independently of one another represents 0 or 1,a, b and c independently of one another denote 1 or 2,a+c<4, a+b+c=3 or 5andX and Y denote different mono- or bivalent radicals,a process for their preparation and their use for dyeing and printing cellulose-containing fibre materials, in particular paper by means of the ink jet process, have been found.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: June 10, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karin Hassenruck, Peter Wild, Frank-Michael Stohr
  • Patent number: 5631352
    Abstract: Dye mixtures which comprise at least one anionic acid dye of the formula ##STR1## together with at least one anionic acid dye of the formula ##STR2## in which the substituents are as defined in claim 1, and the novel dyes of the formulae (1) and (2) are direct dyes for cellulosic fibre materials in particular. They have a high heat stability and are particularly suitable for one-bath, one-stage dyeing of polyester/cotton blend fabrics with a disperse dye for the polyester fibres under the dyeing conditions for polyester fibres.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: May 20, 1997
    Assignee: Ciba-Geigy Corporation
    Inventor: Urs Lauk
  • Patent number: 5536818
    Abstract: A dichroic dye represented by the formula (I) or (II): ##STR1## wherein the substituents are as described in the specification. The dichroic dyes (I) and (II) exhibit excellent dichroism and can be prepared from 2,2'-ditrifluoromethylbenzidine having no toxicity, such as mutagenicity.
    Type: Grant
    Filed: November 4, 1994
    Date of Patent: July 16, 1996
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Masaharu Kaneko, Hisayo Ishio
  • Patent number: 5493011
    Abstract: Water-insoluble azo colorants, their preparation and use The invention relates to monoazo and disazo compounds of the formula (I) ##STR1## in which D is the radical of a carbocyclic or heterocyclic diazo or bisdiazo component, R.sup.1 and R.sup.2, independently of one another, are each a substituted or unsubstituted aryl or heteroaryl radical, X.sup.1 and X.sup.2, independently of one another, are each ring-forming ether oxygen or a substituted or unsubstituted imide grouping and n has the value 0 or 1, in which rings A and B, independently of one another, can each be additionally substituted and/or carry substituted or unsubstituted fused rings.These new compounds of the formula (I) are obtained by coupling diazotized amines or diamines of the type D--NH.sub.2 or H.sub.2 N--D--NH.sub.2 with (benzoxazol-2-yl)- or (benzimidazol-2-yl)-arylacetamides.Depending on the presence and length of alkyl chains, the compounds of the formula (I) are suitable for use as pigments, disperse dyes or oil-soluble dyes.
    Type: Grant
    Filed: November 6, 1992
    Date of Patent: February 20, 1996
    Assignee: Hoechst AG
    Inventors: Rudiger Jung, Reinhold Deubel
  • Patent number: 5489671
    Abstract: A trisazo compound represented by the following formula (1) in the free acid form: ##STR1## wherein Q' is phenylene group, Q.sup.2 is phenyl or naphtyl group, one of the A and B is a hydroxy group and the other is an amino group, K is 1 or 2, one of m and n is 1 and the other is 0, X and Y independently of one another are each --OR.sup.1, --SR.sup.2, --NR.sup.3 R.sup.4 or ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently of one another are each a hydrogen atom, an alkyl, phenyl or naphthyl group; r is 1 or 2; and Z is --CH.sub.2 --, --O--, --SO.sub.2 -- or --NR.sup.5 -- wherein R.sup.5 is a hydrogen atom or C.sub.1 -C.sub.4 alkyl group;a method for dyeing fiber material, paper or leather by using the trisazo compound;and an ink which contains the trisazo compound and which is excellent in storage stability and can give a clear black printed image having excellent water resistance and light fastness.
    Type: Grant
    Filed: September 27, 1994
    Date of Patent: February 6, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazuya Ogino, Yuriko Tamura, Takashi Omura, Mahito Fujita, Hideo Kawashita, Koji Aburada
  • Patent number: 5484899
    Abstract: The invention relates to compounds of the formula ##STR1## in which the variables are as defined in the claims. The compounds are suitable as dyes, in particular for dyeing and printing cellulosic fibre materials, and produce dyeings and prints with good all-round fastness properties.
    Type: Grant
    Filed: May 3, 1994
    Date of Patent: January 16, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Rolf Deitz, Athanassios Tzikas
  • Patent number: 5466282
    Abstract: Disclosed herein is a monoazo dye compound having a structural unit represented by the following formula in its molecule:--X--Y--(R.sub.1)(R.sub.2)(R.sub.3).sub.k [I]wherein Y is a 6-membered ring containing 2 or 3 nitrogen atoms, X is a linking group for bonding a main body of the dye molecule to Y, R.sub.1 is the first amino acid residue, R.sub.2 is an atomic group selected from the following group A, R.sub.3 is another atomic group selected from the following group BB, and k is a number of 0 or 1:Group A: H, OH, NH.sub.2, CN, .dbd.O and the second amino acid residue;Group BB: H, OH, NH.sub.2, CN and .dbd.O,the first and second amino acid residues being identical with or different from each other.
    Type: Grant
    Filed: May 12, 1994
    Date of Patent: November 14, 1995
    Assignee: Canon Kabushiki Kaisha
    Inventors: Tsuyoshi Eida, Osamu Nishiwaki, Takao Yamamoto, Kumiko Mafune
  • Patent number: 5328995
    Abstract: The compounds of the formula ##STR1## where the substituents are as defined in claim 1, are direct dyes for various substrates, in particular cellulosic fibre materials. They are high temperature resistant and therefore are particularly highly suitable for the one-bath, single-stage dyeing of polyester/cotton blend fabrics with a disperse dye for the polyester fibres under the dyeing conditions for polyester fibres.
    Type: Grant
    Filed: January 27, 1993
    Date of Patent: July 12, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Rudolf Schaulin, Urs Lauk
  • Patent number: 5225545
    Abstract: The compounds of the formula (1) indicated in claim 1 are suitable for use as direct dyes for dyeing and printing a wide range of materials, in particular cellulose-containing fibre materials, producing dyeings and prints having good fastness properties.
    Type: Grant
    Filed: May 12, 1992
    Date of Patent: July 6, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Urs Lauk
  • Patent number: 5183501
    Abstract: An ink composition for ink jet recording, which contains a water-soluble dye, an organic solvent and water, in which the dye is represented by the formula (1) as shown in the state of free acid:D--(SO.sub.2 CH.sub.2 CH.sub.2 SO.sub.3 H).sub.m (1)wherein D represents a dye residue selected from the group of monoazo and polyazo dyes, their complexes with Cr, Fe, Co and Cu, copper and nickel phthalocyanine dyes, anthraquinone dyes, dioxazine dyes, and formazane complex dyes, and m represents an integer of 1, 2, 3 or 4, and which is superior in its stability during preservation and while being used, thermal stability, image clearness, water resistivity, light fastness, etc.
    Type: Grant
    Filed: October 11, 1991
    Date of Patent: February 2, 1993
    Assignees: Sumitomo Chemical Company, Limited, Taoka Chemical Co. Ltd.
    Inventors: Hideo Kawashita, Mituhiro Ohta, Kazuya Ogino
  • Patent number: 5178671
    Abstract: Provided is an ink comprising a recording agent and a liquid medium for dissolution or dispersion thereof, the recording agent being a compound represented by the general formula ##STR1## where R.sup.1 is a radical selected from the group of lower alkyl, lower alkoxy, --COOM, and --SO.sub.3 M; R.sup.2 and R.sup.3 are respectively a radical selected from the group of hydrogen, lower alkyl, lower alkoxy, amino, --NHCOCH.sub.3, --SO.sub.3 M, and --COOM; R.sup.4 and R.sup.5 are respectively a radical selected from the group of lower alkyl, lower alkoxy, --NHCOCH.sub.3, --SO.sub.3 M, and COOM; A is ##STR2## R.sup.6 is a radical selected from the group of acetyl, benzoyl, --SO.sub.2 C.sub.6 H.sub.5, --SO.sub.2 C.sub.6 H.sub.4 --CH.sub.3, phenyl, which is unsubstituted or substituted by --COOM or methyl, and ##STR3## R.sup.7 and R.sup.8 are respectively a radical selected from the group of hydrogen, hydroxyl, and --C.sub.2 H.sub.4 OH; R.sup.9 and R.sup.
    Type: Grant
    Filed: June 11, 1992
    Date of Patent: January 12, 1993
    Assignee: Canon Kabushiki Kaisha
    Inventors: Takao Yamamoto, Tsuyoshi Eida, Mayumi Yamamoto
  • Patent number: 4997919
    Abstract: This invention relates to direct dyes for various substrates, in particular cellulosic fiber materials. The inventive dyes are high-temperature-resistant and highly suitable for the single bath, one step dyeing of polyester/cotton mixed fabrics with a disperse dye for the polyester fibers under the dyeing conditions for polyester fibers.The inventive dyes are of the formula ##STR1## in which A is a radical of the formula ##STR2## A' has the meaning of A or is a mono- or polyazo dye radical which is different from A, R and R', independently of one another, are hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by chlorine, hydroxyl, cyano, carboxyl, sulfo, sulfato, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl, R.sub.1 is hydroxyl, C.sub.1 -C.sub.4 alkoxy, halogen, C.sub.1 -C.sub.4 alkylthio, amino, N-mono- or N,N-di-C.sub.1 -C.sub.4 alkylamino which is unsubstituted or substituted in the alkyl moiety by hydroxyl, carboxyl or C.sub.1 -C.sub.
    Type: Grant
    Filed: June 19, 1989
    Date of Patent: March 5, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Schaulin
  • Patent number: 4990421
    Abstract: An electrophotographic recording material comprising a conductive support and a photosensitive layer containing a photoconductive compound that has p-type charge generating capacity and is a trisazo compound which is the reaction product of the coupling reaction between a coupler compound that does not contain a carboxylic acid or sulphonic acid group and a diazonium salt represented by the following general formula (I): ##STR1## wherein: each of L, M and Y (same or different) represents a phenylene group including a phenylene groups substituted with one or more substituents selected from the group consisting of lower alkyl (C.sub.1 -C.sub.2), nitro, methoxy, ethoxy or halogen, or represents said phenylene group fused-on with the necessary atoms to close a saturated or unsaturated carbocyclic or heterocyclic ring or ring system including said ring or ring-system in substituted form, and X.sup.- is an anion.
    Type: Grant
    Filed: July 14, 1989
    Date of Patent: February 5, 1991
    Assignee: Agfa-Gevaert, N.V.
    Inventors: David R. Terrell, Marcel J. Monbaliu, Carina Geelen, Guy P. Verbeek, Frans C. De Schrijver, Mark G. Van der Auweraer
  • Patent number: 4988593
    Abstract: An electrophotographic photosensitive member having a photosensitive layer is formed on a support and contains an azo pigment expressed by a general formula [I] or [II]: ##STR1## where A, B.sub.1 and B.sub.2 are aromatic hydrocarbon nucleus groups or heterocyclic groups which may be optionally linked by coupler groups, A is an univalent group, B.sub.1 is an univalent, bivalent or trivalent group, and B.sub.2 is a bivalent or trivalent group; X is a residue necessary for forming a polycyclic aromatic nucleus or a heterocycle by condensation with a benzene nucleus; R is a halogen atom, an alkyl group or an alkoxy group; n.sub.1 is an integer from 1 to 3; and n.sub.2 is an integer from 1 to 3. This photosensitive layer may be composed of a charge generation layer containing the above azo pigment and a charge transport layer.
    Type: Grant
    Filed: September 20, 1989
    Date of Patent: January 29, 1991
    Assignee: Canon Kabushiki Kaisha
    Inventor: Hideyuki Takai
  • Patent number: 4917981
    Abstract: A photosensitive member for electrophotography which comprises a photosensitive layer containing at least one member of the group consisting of thiophene structure-containing azo compounds having one of the general formulae (I) to (X): ##STR1## wherein all the symbols are defined in the specification.
    Type: Grant
    Filed: December 28, 1987
    Date of Patent: April 17, 1990
    Assignee: Fuji Electric Co., Ltd.
    Inventors: Yoichi Nakamura, Masami Kuroda, Noboru Furusho
  • Patent number: 4799960
    Abstract: 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;q is 1/2 or 1p is 1 or 2L is a transition metal capable of complexing with a dyeM is H, ammonium, or a monovalent metal;Q is H or SO.sub.3 MT is H or C.sub.1-4 -alkyl;D is a substituted azo group;B, E and F are H or substituents;X is NR.sup.1 R.sup.2, NR.sup.3 R.sup.4, --NR.sup.3 --Z--NR.sup.4 --, OR.sup.3, or the residue of a mono- or bis-azo chromophore comprising benzene, naphthalene or mono- or bi- cyclic heteroaryl diazo and coupling components, linked to the triazine nucleus through a primary or secondary amine linking group, wherein R.sup.3 & R.sup.
    Type: Grant
    Filed: November 10, 1986
    Date of Patent: January 24, 1989
    Assignee: Canon Kabushiki Kaisha
    Inventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
  • Patent number: 4780532
    Abstract: 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 & R.sup.2 together with the nitrogen atom form a morpholine ringa & b are different and from 1 to 8m is from 1 to 10;n is from 0 to 9;q is 1/2 or 1p is 1 or 2L is a transition metal capable of complexing with a dyeM is H, ammonium, or a monovalent metal;B, D, F & E are H or substituents;X is NR.sup.1 R.sup.2, NR.sup.3 R.sup.4, --NR.sup.3 --Z--NR.sup.4 --, OR.sup.3, or the residue of a mono- or dis-azo chromophore comprising benzene, naphthalene or hetero-mono- or bi-cyclic diazo and coupling components, linked to the triazine nucleus through a primary or secondary amino linking group in which R.sup.3 and R.sup.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: October 25, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
  • Patent number: 4746733
    Abstract: 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 & R.sup.2 together with the nitrogen atom form a morpholine ring;a & b are different and from 1 to 8;m is from 1 to 10;n is from 0 to 9;Y is a triphendioxazinylene (TPD) group;M is H, ammonium, or a metal;X is NR.sup.1 R.sup.2, alkoxy, NR.sup.3 R.sup.4 in which R.sup.3 and R.sup.4 are each independently selected from H, alkyl, aryl and heteroaryl, or the residue of a mono- or dis-azo chromophore comprising benzene, naphthalene or mono- or bi-cyclic heteroaryl diazo and coupling components, linked to the triazine nucleus through a primary or secondary amine linking group;andZ is an alkylene, arylene or aralkylene group,suitable for the preparation of a printing ink, especially for ink jet printing.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: May 24, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
  • Patent number: 4734218
    Abstract: Provided are novel dichroic azo dyestuffs, which contain skeletons represented by the following general formula: ##STR1## at one terminals of the long axes of the molecules of the azo dyestuffs, and liquid crystal compositions containing the dichroic azo dyestuffs in forms dissolved in liquid crystals. These dichroic azo dyestuffs have large dichroic ratios and high durability, and their compositions are employed as useful display devices.
    Type: Grant
    Filed: July 18, 1986
    Date of Patent: March 29, 1988
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Keisuke Takuma, Kimitoshi Kato, Hiroshi Aiga, Yasuyuki Yamada, Tsutomu Nishizawa
  • Patent number: 4705528
    Abstract: 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 & R.sup.2 together with the nitrogen atom form a morpholine ringa & b are different and from 1 to 8m is from 1 to 10;n is from 0 to 9;q is 1/2 or 1p is 1 or 2L is a transition metal capable of complexing with a dyeM is H, ammonium, or a monovalent metal;Q is H or SO.sub.3 MT is H or C.sub.1-4 -alkyl;D is a substituted azo group;B, E & F are H or substituents;X is NR.sup.1 R.sup.2, NR.sup.3 R.sup.4, --NR.sup.3 --Z--NR.sup.4 --, Or.sup.3, or the residue of a mono- or bis-azo chromophore comprising benzene, naphthalene or mono- or bi- cyclic heteroaryl diazo and coupling components, linked to the triazine nucleus through a primary or secondary amine linking group, wherein R.sup.3 & R.sup.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: November 10, 1987
    Assignee: Imperial Chemical Industries PLC
    Inventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
  • Patent number: 4703113
    Abstract: 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 & R.sup.2 together with the nitrogen atom form a morpholine ringa & 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: Grant
    Filed: August 12, 1985
    Date of Patent: October 27, 1987
    Assignee: Imperial Chemical Industries PLC
    Inventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
  • Patent number: 4670547
    Abstract: Tetrakisazo compounds of the formula ##STR1## and salts thereof, whereinB is ##STR2## wherein B.sub.1 is a bridging radical as defined in the specification,R.sub.7 is hydrogen or C.sub.1-4 alkyl,R.sub.8 is hydrogen or C.sub.1-4 alkyl, andeach Y is independently halo, hydroxy, amino, hydroxyamino, C.sub.1-4 alkoxy, phenoxy, substituted phenoxy, an aliphatic, cycloaliphatic or aromatic amine radical or a saturated heterocyclic amine radical,each D is independently mono-, di- or tri-sulfonaphthyl or ##STR3## wherein R.sub.2 is hydrogen, halo, carboxy, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy, --COOR.sub.4, (C.sub.1-4 alkyl)carbonylamino or (C.sub.1-4 alkoxy)carbonylamino, wherein R.sub.4 is C.sub.1-4 alkyl, phenyl, benzyl or phenyl or benzyl substituted by 1 or 2 substituents selected from halo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy,R.sub.3 is hydrogen, halo, hydroxy, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, andm is 0, 1 or 2,each M is independently ##STR4## wherein R.sub.5 is hydrogen, halo, C.sub.
    Type: Grant
    Filed: November 8, 1984
    Date of Patent: June 2, 1987
    Assignee: Sandoz Ltd.
    Inventor: Friedrich Lehr
  • Patent number: 4667019
    Abstract: Compounds of the general formula I ##STR1## where n is 0, 1 or 2, R.sup.1 and R.sup.2 are each hydrogen, unsubstituted or substituted alkyl, cycloalkyl, aralkyl, aryl, acyl, alkoxycarbonyl or aryloxycarbonyl, or together form alkylene or an unsubstituted or substituted benzo ring and Y is a radical of the formula ##STR2## where the rings A, B and C can be further substituted or benzo-fused, R.sup.3 and R.sup.4 are each hydrogen or unsubstituted or substituted alkyl, aralkyl or cycloalkyl, or, together with the nitrogen, form piperidino, pyrrolidino or morpholino, R.sup.5 is hydrogen, unsubstituted or substituted alkyl, cycloalkyl, aralkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, alkylsulfonyl, or arylsulfonyl and R.sup.6 is hydrogen, alkyl or cycloalkyl. These compounds are useful as pleochroic dyes and have a good degree of order coupled with high solubility and good stability in the liquid crystal matrix.
    Type: Grant
    Filed: January 13, 1986
    Date of Patent: May 19, 1987
    Assignee: Kernforschungszentrum Karlsruhe GmbH
    Inventors: Karl-Heinz Etzbach, Peter Neumann
  • Patent number: 4594410
    Abstract: Azo dyes of the formula ##STR1## and external salts thereof, wherein F is the residue of a monoazo or disazo compound in 1:1 metal complex form or of a trisazo, disazoazoxy or tetrakisazo compound in metal-free or 1:1 metal complex form,each X is independently --NR.sub.2 --Q--NR.sub.3 R.sub.4 or --NR.sub.2 --Q--N.sup..sym. R.sub.5 R.sub.6 R.sub.7,whereinQ is linear or branched C.sub.2-6 alkylene or --NH--CO--CH.sub.2 --,R.sub.2 is hydrogen or C.sub.1-4 alkyl,each of R.sub.3 and R.sub.4 is independently hydrogen; C.sub.1-6 alkyl; C.sub.2-6 alkyl monosubstituted by cyano or hydroxy in the 2-, 3-, 4-, 5- or 6-position; phenyl(C.sub.1-3 alkyl); phenyl(C.sub.1-3 alkyl) having, on the phenyl ring, 1, 2 or 3 substituents selected from chloro, C.sub.1-4 alkyl and C.sub.1-4 alkoxy; C.sub.5-6 cycloalkyl or C.sub.5-6 cycloalkyl substituted by 1, 2 or 3 C.sub.1-4 alkyl groups or --NR.sub.3 R.sub.
    Type: Grant
    Filed: August 18, 1982
    Date of Patent: June 10, 1986
    Assignee: Sandoz Ltd.
    Inventor: Reinhard Pedrazzi
  • Patent number: 4492653
    Abstract: Water soluble trisazo dyestuffs of the formula ##STR1## in which A is 1-amino-8-naphthol-3,6-disulfonic acid or 1-amino-8-naphthol-4,6-disulfonic acid, or a mixture of these two compounds, and B is 1-(3'- or 4'-aminophenyl)-3-methyl-5-pyrazolone, a process for their manufacture by diazotizing component A and coupling it with 3,3'-dihydroxy-diphenylamine to give a monoazo dyestuff, reacting this dyestuff with diazotized component B to give a disazo dyestuff, and converting this dyestuff to the trisazo dyestuff by uniting it with diazotized 4-nitro-4'-amino-diphenylamine-2-sulfonic acid, or by operating as described while, however, changing the sequence of reaction of component B and 4-nitro-4'-amino-diphenylamine-2-sulfonic acid, and use of these dyestuffs for the dyeing of leather and fur.
    Type: Grant
    Filed: August 23, 1982
    Date of Patent: January 8, 1985
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Karl Sommer, Norbert Armbrecht
  • Patent number: 4485042
    Abstract: Leathers can be advantageously dyed with water-soluble polyazo dyestuffs having, in the form of the free acid, the formula ##STR1## wherein A is a member of the benzene, naphthalene or heterocyclic series;B has the formula ##STR2## n is the number 1 or 2; m is a number from 1 to 4;X is hydroxyl or amino;Y is hydroxyl or amino but X differs from Y;Z is hydroxyl or amino unsubstituted or substituted by alkyl having 1 to 4 carbon atoms, alkanoyl having 1 to 4 carbon atoms or by a moiety of the formula ##STR3## R.sup.1 is hydrogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms or alkoxyalkoxy having 3 to 7 carbon atoms; andR.sup.2 and R.sup.3 independently of one another are each hydrogen or alkyl having 1 to 4 carbon atoms.
    Type: Grant
    Filed: August 20, 1982
    Date of Patent: November 27, 1984
    Assignee: Cassella Aktiengesellschaft
    Inventors: Norbert Armbrecht, Wolfgang Bauer, Joachim Ribka