Amine Salt Patents (Class 534/728)
  • Patent number: 7470780
    Abstract: The present invention relates to dyes of formula (1) that are soluble in organic solvents, wherein Cat+ is an organic cation, to a process for their preparation and to their use in the production of colored plastics or polymeric color particles, printing colorants, printing pastes and printing inks.
    Type: Grant
    Filed: December 19, 2005
    Date of Patent: December 30, 2008
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Thomas Ruch, Ursula Luterbacher
  • Patent number: 6632932
    Abstract: The objective of the present invention is to provide a high-purity trisazo compound with excellent light resistance that is useful as a coloring matter for a black aqueous ink for ink jet recording and the like. Thus, the present invention provides a trisazo compound represented by the formula: wherein A1 is a group represented by the formula —COOM or —SO3M, A2 is a hydrogen atom or a group represented by the formula —COOM or —SO3M, M is each independently a hydrogen atom, or onium, R is each independently a hydrogen atom, an alkyl group, an alkoxy group and the like, B is a residue of K acid, Nps is a residue of &ggr; acid, J acid, or RR acid.
    Type: Grant
    Filed: October 25, 2002
    Date of Patent: October 14, 2003
    Assignee: Orient Chemical Industries, Ltd.
    Inventors: Yoshihiro Sawatari, Makiko Matsui, Shuji Sugawara
  • Patent number: 6451989
    Abstract: Provided are novel black azo dyes which are useful in ink compositions, especially ink jet ink compositions. The dyes and ink compositions of the present invention exhibit a good balance of optical density, print reliability, water fastness and light fastness.
    Type: Grant
    Filed: June 18, 2001
    Date of Patent: September 17, 2002
    Assignee: Lexmark International, Inc.
    Inventors: Bradley Leonard Beach, Ann P Holloway, James F Feeman
  • Patent number: 6320031
    Abstract: Monoazo dyes of formula (3) wherein A, R1, R2, M and n 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: February 23, 2000
    Date of Patent: November 20, 2001
    Assignee: Ilford Imaging Switzerland GmbH
    Inventors: Kurt Baettig, GĂ©rald Jan
  • Patent number: 6288217
    Abstract: Provided are novel black azo dyes which are useful in ink compositions, especially ink jet ink compositions. The dyes and ink compositions of the present invention exhibit a good balance of optical density, print reliability, water fastness and light fastness.
    Type: Grant
    Filed: August 18, 2000
    Date of Patent: September 11, 2001
    Assignee: Lexmark International, Inc.
    Inventors: Bradley Leonard Beach, Ann P Holloway, James F Feeman
  • Patent number: 6160169
    Abstract: A process for preparing amine salts of 4-nitrotoluene-2-sulfonic acid by sulfonation of nitrotoluene with oleum, subsequent dilution of the reaction mixture with water and extraction with lipophilic amines, wherein the acidic aqueous solution of the sulfonation product is partially neutralized with mineral bases. The compounds prepared according to the invention are particularly suitable for preparing dyes.
    Type: Grant
    Filed: December 7, 1998
    Date of Patent: December 12, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Rudolf Bermes, Armin Haag, Hellmut Kast, Peter Krotzsch
  • Patent number: 6130319
    Abstract: A flocculating dye reduces bleed between two inks when they are applied side by side. A first ink comprises the flocculating dye which flocculates the dispersant-pigment of the second ink.
    Type: Grant
    Filed: April 3, 1998
    Date of Patent: October 10, 2000
    Assignee: Lexmark International, Inc.
    Inventors: James F. Feeman, Jing X. Sun
  • Patent number: 6084078
    Abstract: The novel disazo dyestuffs of the formula (I) in which the substituents and indices have the meanings given in the description, are outstandingly suitable for dyeing cellulosic materials in red-violet to blue brilliant color shades.
    Type: Grant
    Filed: December 17, 1997
    Date of Patent: July 4, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventor: Winfried Mennicke
  • Patent number: 6031083
    Abstract: The new disazo dyestuffs of the formula (I) ##STR1## wherein the substituents and the indices have the meanings given in the description,wherein more than 25 equivalent % of all the M cations in the molecule are alcohol ammonium radicals of the formula .sup..sym. NR.sub.1 R.sub.2 R.sub.3 R.sub.4 whereinR.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently of one another represent hydrogen, C.sub.1 -C.sub.4 -alkyl and C.sub.2 -C.sub.4 -hydroxyalkyl, with the proviso that at least one of the radicals R.sub.1 -R.sub.4 denotes C.sub.2 -C.sub.4 -hydroxyalkyl,are excellently suitable for dyeing cellulose-containing materials, and in particular paper, and are distinguished by high degrees of fastness.
    Type: Grant
    Filed: March 19, 1999
    Date of Patent: February 29, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Kunde, Wolfgang Zarges
  • Patent number: 5997628
    Abstract: Disclosed are red shade yellow compositions characterized by the formula: ##STR1## wherein X is a lower alkyl or a --COOR.sub.1 group; wherein R.sub.1 is a hydrogen or lower alkyl group; each Y is independently a lower alkyl, lower alkyloxy or halogen group; a is 0, 1, or 2; and M is a divalent metal. Also disclosed is a process for preparing red shade yellow pigment compositions prepared by initially a diazonium component comprised of one or more aromatic amines wherein at least one of said amines is a 1-sulfo-2-naphthylamine; and thereafter coupling the diazonium component with a coupling component comprised of a pyrazolone coupler to form a dye, and metallizing said dye with at least one divalent metal.
    Type: Grant
    Filed: June 8, 1998
    Date of Patent: December 7, 1999
    Assignee: Engelhard Corporation
    Inventor: Amrit Pal Bindra
  • Patent number: 5986075
    Abstract: The present invention relates to a process for desalting aqueous suspensions containing an organic diazonium compound and electrolytes containing Na ions, in which the aqueous suspension is passed through a semipermeable membrane.
    Type: Grant
    Filed: January 20, 1999
    Date of Patent: November 16, 1999
    Assignees: Bayer Corporation, Bayer Aktiengesellschaft
    Inventors: John C. DuBose, Andrew D. Johnson, Samuel Shaun Murphree, Edzard Tholema, Helmut Hoffmann, Wolfgang Zarges, Wolfgang Frank, Bettina Burkhardt
  • Patent number: 5965716
    Abstract: A salt of formula IF.sub.n.A (I)in which F is the residue of a metal free anionic dyestuff having 1 to 4 acids groups,n is 1 to 2; andA is a group containing 1 to 4 sterically hindered amine groups and at least n ammonium or immonium groups.
    Type: Grant
    Filed: April 25, 1997
    Date of Patent: October 12, 1999
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Bansi Lal Kaul, Angelos-Elie Vougioukas
  • Patent number: 5919915
    Abstract: An azo pyrazolone compound of the formula: ##STR1## wherein Z represents a substituent selected from Cl, Br, F, NO.sub.2, SO.sub.2 R, CO.sub.2 R, NHSO.sub.2 R.sup.1 and NHCOR.sup.1 in which R and R.sup.1 are hydrocarbyl groups and the sulphonic acid group in ring A is in the 3- or 4-position relative to the pyrazolyl group, said compound being in the form of a salt, and its use as a pigment.
    Type: Grant
    Filed: July 17, 1997
    Date of Patent: July 6, 1999
    Assignee: Zeneca Limited
    Inventors: Alan Patrick Chorlton, James Mason
  • Patent number: 5892105
    Abstract: A process for preparing amine salts of 4-nitrotoluene-2-sulfonic acid by sulfonation of nitrotoluene with oleum, subsequent dilution of the reaction mixture with water and extraction with lipophilic amines, wherein the acidic aqueous solution of the sulfonation product is partially neutralized with mineral bases.The compounds prepared according to the invention are particularly suitable for preparing dyes.
    Type: Grant
    Filed: December 9, 1997
    Date of Patent: April 6, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Rudolf Bermes, Armin Haag, Hellmut Kast, Peter Krotzsch
  • Patent number: 5834600
    Abstract: Disclosed are diazahemicyanine hydrophobic cationic dyes represented by the formula (1): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are lower alkyl groups having not more than 5 carbon atoms, R.sup.5 is a lower alkyl group having not more than 5 carbon atoms or a lower alkoxy lower alkyl group having not more than 6 carbon atoms, and Z.sup.- is a counter ion having a hydrophobic organic group,and a thermal transfer ink ribbon having a substrate and and ink layer laminated thereon containing said cationic dye.
    Type: Grant
    Filed: June 28, 1996
    Date of Patent: November 10, 1998
    Assignees: Sony Corporation, Hodogaya Chemical Co., Ltd.
    Inventors: Masanobu Hida, Kengo Ito, Yoshio Fujiwara, Nobuo Suzuki, Hiroyoshi Yamaga, Junichi Hagiwara
  • Patent number: 5770708
    Abstract: A process for preparing aqueous preparations of azo dyes of the formula ##STR1## where R is hydrogen or C.sub.1 -C.sub.4 -alkyl andKat.sym. is the equivalent of a cation which derives from a tertiary amine of the ethanolamine or propanolamine series,by diazotization of an aniline of the formula ##STR2## with neopentylglycol dinitrite in an aqueous medium and coupling of the resulting reaction mixture with .beta.-naphthol in the presence of a water-miscible diluent and of an amine comprises using an amine comprising a tertiary amine of the ethanolamine or propanolamine series.
    Type: Grant
    Filed: May 27, 1997
    Date of Patent: June 23, 1998
    Assignee: BASF Aktiengesellschaft
    Inventor: Rudolf Bermes
  • Patent number: 5744590
    Abstract: An azo pyrazolone compound of the formula: ##STR1## in the form of a salt, and its use as a pigment.
    Type: Grant
    Filed: July 17, 1997
    Date of Patent: April 28, 1998
    Assignee: Zeneca Limited
    Inventors: Alan Patrick Chorlton, James Mason
  • Patent number: 5684140
    Abstract: There is described a new magenta azo dye which can be used in an aqueous composition in an ink-jet printing process.
    Type: Grant
    Filed: December 16, 1996
    Date of Patent: November 4, 1997
    Assignee: Ilford A.G.
    Inventors: Kurt Baettig, Gerald Jan
  • Patent number: 5616694
    Abstract: A compound of Formula (1) and salts thereof wherein the variables are as defined in the specification:Ar.sup.1 N.dbd.N-J-X-L-X-J-N.dbd.NAr.sup.2 (1)A compound of Formula (1) is suitable for use in the coloration of cellulosic substrates, such as paper, to give bright prints with good light and water fastness. It is especially suitable for use in the printing of paper by non-impact printing techniques, such as ink jet printing, especially thermal ink jet printing.
    Type: Grant
    Filed: July 12, 1995
    Date of Patent: April 1, 1997
    Assignee: Zeneca Limited
    Inventors: Ronald W. Kenyon, Prahalad M. Mistry
  • Patent number: 5597387
    Abstract: The present invention relates to water-soluble polyazo dyestuffs of the general formula I ##STR1## wherein Y, Z, m and M.sup..sym.1 to M.sup..sym.4 are as defined in claim 1, processes for dyeing leather and paper with the polyazo dyestuffs, and recording liquids and inks containing the polyazo dyestuffs.
    Type: Grant
    Filed: November 9, 1995
    Date of Patent: January 28, 1997
    Assignee: Hoechst AG
    Inventors: Wolfgang Bauer, Dieter Baumgart, Walter Zoller
  • Patent number: 5571899
    Abstract: Salts of the formulaF.sub.n.A,wherein F is an anion of a metal-free anionic dye having m acid groupswherein m is 1 to 4, inclusive,A is a cation of an amine containing 1 to 6 sterically hindered amine groups, andn is 1 or 2,with the proviso that the salt contains 1 to n.times.m groups selected from ammonium and immonium groups, useful as pigments, particularly for the coloring of solvent-free and solvent-containing plastic materials, lacquers and printing inks.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: November 5, 1996
    Assignee: Sandoz, Ltd.
    Inventors: Bansi L. Kaul, Angelos-Elie Vougioukas
  • Patent number: 5556885
    Abstract: There are provided N-arylthiohydrazone derivatives of formula I ##STR1## the use thereof for the control of insect and acarid pests and methods and compositions for the protection of crops from the damage and loss caused by said pests.
    Type: Grant
    Filed: October 27, 1994
    Date of Patent: September 17, 1996
    Assignee: American Cyanamid Company
    Inventors: Susan Trotto, Joseph A. Furch, III, David G. Kuhn, David A. Hunt
  • Patent number: 5554735
    Abstract: Azo oxime ethers of formula (I), in which X is CH or N, R.sub.1 is hydrogen, C.sub.1 -C.sub.3 alkyl, trifluoromethyl or cylclopopy and R.sub.2 is aryl or heteroaryl, have an activity against phytopathogenic fungi. They can be used in the form of formulaions as crop protection products, seed-dressing products and wood preservatives.
    Type: Grant
    Filed: August 26, 1994
    Date of Patent: September 10, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Hugo Ziegler, Stephan Trah
  • Patent number: 5523387
    Abstract: This invention relates to dyes in salt form which are useful for mass dyeing of synthetic polymers. In particular, this invention relates to ammonium or immonium salt-containing dyes that display good polymer affinity, and the methods for using those dyes to color polymeric substrates.
    Type: Grant
    Filed: June 14, 1994
    Date of Patent: June 4, 1996
    Assignee: Sandoz Ltd.
    Inventors: Jurgen Goldmann, Bansi L. Kaul
  • Patent number: 5519121
    Abstract: Novel dyestuffs of the formula (I) ##STR1## in which DK denotes a radical of the formula ##STR2## where m is 1 or 2 and DK' denotes a radical of the formula ##STR3## where n is 1 or 2 R.sub.1 represents hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkyl,R.sub.2 represents hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,R.sub.3 represents substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -acylamino andR.sub.4 represents substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl.have now been found.The invention also relates to a process for their preparation and to their use for dyeing/coloring and printing textiles and paper, in particular in printing inks containing these dyestuffs.
    Type: Grant
    Filed: February 24, 1995
    Date of Patent: May 21, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerd-Friedrich Renner, Peter Wild, Karin Hassenruck
  • Patent number: 5510467
    Abstract: Salts of the formulaF.sub.n .multidot.A,wherein F is an anion of a metal-free anionic dye having m acid groupswherein m is 1 to 4, inclusive,A is a cation of an amine containing 1 to 4 sterically hindered amine groups, andn is 1 or 2,with the proviso that the salt contains 1 to n.times.m groups selected from ammonium and immonium groups, useful as pigments, particularly for the coloring of solvent-free and solvent-containing plastic materials, lacquers and printing inks.
    Type: Grant
    Filed: December 13, 1993
    Date of Patent: April 23, 1996
    Assignee: Sandoz Ltd.
    Inventors: Bansi L. Kaul, Angelos-Elie Vougioukas
  • 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: 5473053
    Abstract: A compound of Formula (1) and salts thereof:Ar.sup.1 N.dbd.N--J--X--L--X--J--N.dbd.NAr.sup.2 (1)wherein: ##STR1## Ar.sup.1 and Ar.sup.2 are each independently aryl containing at least two carboxy groups; andL is a group of the Formula (3a) or (3b): ##STR2## in which T.sup.1 and T.sup.2 each independently is C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy or C.sub.3-4 -alkenyl;T.sup.3 and T.sup.4 each independently is H, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy or C.sub.3-4 -alkenyl provided that T.sup.3 and T.sup.4 are not both H;each X independently is a group of the Formula (4), (5) or (6): ##STR3## each Z independently is H, halogen, alkyl, NR.sup.1 R.sup.2, SR.sup.3 or 0R.sup.3 ;each Y independently is Z, SR.sup.4 or OR.sup.4 ;each E independently is Cl or CN; andR.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each as defined in the specification.A compound of Formula (1) is suitable for use in the coloration of cellulosic substrates, such as paper, to give bright prints with good light and water fastness.
    Type: Grant
    Filed: January 7, 1994
    Date of Patent: December 5, 1995
    Assignee: Zeneca Limited
    Inventors: Ronald W. Kenyon, Prahalad M. Mistry
  • Patent number: 5453495
    Abstract: A compound of Formula (1) and salts thereof: ##STR1## wherein: L is optionally substituted piperazinyl;D is optionally substituted phenylene or naphthylene;E is optionally substituted phenylene, naphthylene or quinoline;R is H or C.sub.1-4 -alkyl;Z is optionally substituted carboxyaryl; andn has a value of 0 or 1.A compound of Formula (1) is useful as a colorant for black inks suitable for ink jet printing.
    Type: Grant
    Filed: December 22, 1994
    Date of Patent: September 26, 1995
    Assignee: Zeneca Limited
    Inventors: Peter Gregory, Ronald W. Kenyon, Prahalad M. Mistry
  • Patent number: 5446134
    Abstract: Bis(perfluorosulphonyl)methanes, process for preparing same and uses thereof. The compounds of the invention are based on the formula (1/nM)+[(R.sub.F SO.sub.2).sub.2 CY].sup.- in which Y denotes an electron-attracting group chosen from --C.dbd.N and RZ groupings in which Z denotes a carbonyl grouping, sulphonyl grouping or a phosphonyl grouping and R denotes an organic monovalent grouping, M denotes a metal having valency n or an organic group capable of existing in the cationic form, R.sub.F denotes a perfluoroalkyl or perfluoroaryl grouping. Said compounds are especially useful in the production of electrochemical devices.
    Type: Grant
    Filed: July 8, 1993
    Date of Patent: August 29, 1995
    Assignees: Centre National de la Recherche Scientifique, Hydro Quebec
    Inventors: Michel Armand, Djamila Benrabah, Jean-Yves Sanchez
  • Patent number: 5378269
    Abstract: A recording liquid for ink-jet recording comprising coloring matter, which is an image-forming component, and a liquid medium for dissolving the coloring matter therein. The liquid medium is ethanol and the coloring matter is a dye represented by the following general formula (A): ##STR1## or the following general formula (B): ##STR2## as an image-forming component.
    Type: Grant
    Filed: December 29, 1993
    Date of Patent: January 3, 1995
    Assignee: Scitex Digital Printing, Inc.
    Inventors: Louis J. Rossi, Sunita P. Chavan
  • Patent number: 5366543
    Abstract: The present invention provides a disazo salt-forming dye having excellent solubility with organic solvents, especially alcohols and glycols.The present invention thus provides a disazo salt-forming dye represented by the Formula (I): ##STR1## or the Formula (II): ##STR2## wherein Ka.sup.+ represents a cation of an amine which is substituted with at least one linear or cyclic alkyl group or aralkyl group having 6-12 carbon atoms which may be branched or interrupted by oxygen.
    Type: Grant
    Filed: June 9, 1993
    Date of Patent: November 22, 1994
    Assignee: Orient Chemical Industries, Ltd.
    Inventors: Takashi Ono, Tatsuya Yagyu, Tetsui Akase
  • Patent number: 5359064
    Abstract: This invention relates to salts of triazine derivatives with oxygenated as of phoshporus, having general formula (I): ##STR1## obtained by salification, with an acid containing phosphorus, of polycondensates of 2,4,6-triamino-1,3,5-triazine. The compounds having the general formula (I) are particularly used as flame-resistant additives.
    Type: Grant
    Filed: July 10, 1991
    Date of Patent: October 25, 1994
    Assignee: Ministero Dell `Universita` e Della Ricerca Scientifica e Tecnologica
    Inventors: Roberto Cipolli, Enrico Masarati, Gilberto Nucida, Roberto Oriani, Mario Pirozzi
  • 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: 5330542
    Abstract: A dye-incorporated composition which comprises a cyanine type dye and an azo metal chelate compound comprising an azo type compound of the following formula (I): ##STR1## (wherein A is a residue forming a hetero ring together with the carbon atom and the nitrogen atom to which it is bonded, B is a residue forming an aromatic ring or a hetero ring together with the two carbon atoms to which it is bonded, and X is a group having an active hydrogen), and a metal, and an optical recording medium comprising a recording layer which contains the dye-incorporated composition.
    Type: Grant
    Filed: January 24, 1992
    Date of Patent: July 19, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Shuichi Maeda, Satoru Imamura, Kazuo Mitsuhashi, Takako Tsukahara
  • Patent number: 5262527
    Abstract: Anionic azo compounds which, in the free acid form, have the Formula (1): ##STR1## Ar.sup.1 and Ar.sup.2 are each independently aryl or substituted aryl providing at least one of Ar.sup.1 and Ar.sup.2 has at least one substituent selected from COOH and COSH;each R.sup.1 and R.sup.2 is independently H, alkyl, substituted alkyl, alkenyl or substituted alkenyl;L is a divalent organic linking group;n is 0 or 1;each X independently is carbonyl or a group of the formula (2), (3) or (4): ##STR2## each Z independently is NR.sup.3 R.sup.4, SR.sup.5 or OR.sup.5 ; each Y independently is H, Cl, Z, SR.sup.6 or OR.sup.6 ;each E independently is Cl or CN;R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl, substituted aryl, aralkyl, substituted aralkyl or R.sup.3 and R.sup.
    Type: Grant
    Filed: June 28, 1991
    Date of Patent: November 16, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Peter Gregory, Ronald W. Kenyon, Prahalad M. Mistry
  • Patent number: 5258505
    Abstract: Disclosed herein is an azo compound represented by the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 each are a group or atom selected from the group consisting of a hydrogen atom, alkyl groups having 1 to 4 carbon atoms, a methoxy group, halogen atoms, COOM and COOR.sub.4 in which R.sub.4 is an alkyl group having 1 to 4 carbon atoms, and M denotes an alkali metal atom, or an ammonium or organic ammonium ion. An ink containing this compound is suitable for use in an ink-jet recording.
    Type: Grant
    Filed: March 27, 1992
    Date of Patent: November 2, 1993
    Assignee: Canon Kabushiki Kaisha
    Inventors: Tsuyoshi Eida, Mayumi Yamamoto, Takao Yamamoto
  • Patent number: 5254674
    Abstract: A diaminoazothiophene compound represented by the formula (I): ##STR1## salts thereof or metal complexes thereof and a method for preparing the same.
    Type: Grant
    Filed: November 6, 1992
    Date of Patent: October 19, 1993
    Assignee: Osaka Gas Company, Limited
    Inventors: Yasunori Yokomichi, Shinichi Tada, Hitoshi Nishino, Kenji Seki
  • Patent number: 5241058
    Abstract: Azo dye salts corresponding to formula I are suitable as masking couplers. ##STR1## In Formula I, A denotes an optionally substituted aryl group;CC denotes a group optionally carrying a ballast group and capable of coupling under the conditions of photographic color development to produce a dye preferably a cyan dye (color coupler residue);L denotes a linking member which is attached at the coupling position of the color coupler residue by an oxygen, sulphur or nitrogen atom;Z denotes a group conferring solubility in alkalies;R denotes NH--CO--R.sup.1, NH--SO.sub.2 --R.sup.1, COOR.sup.2 or NR.sup.1 --R.sup.2 ;R.sup.1 denotes an optionally substituted alkyl or aryl group;R.sup.2 denotes H or a group such as R.sup.1 ;[M.sup..sym. ] denotes a mixture of organic and inorganic cations optionally containing protons, in which the proportion of organic cation amounts to at least 1/2 mol per mol of dye;m stands for 0, 1 or 2; andn stands for 1, 2, 3 or 4; n.gtoreq.m.
    Type: Grant
    Filed: May 15, 1991
    Date of Patent: August 31, 1993
    Assignee: Agfa-Gevaert Aktiengesellschaft
    Inventors: Gunter Renner, Hans Langen, Ulrich Klein
  • Patent number: 5229503
    Abstract: The invention relates to azo compounds, especially to compounds of formula ##STR1## wherein R.sub.1 is lower alkyl, R.sub.2 is lower alkyl, R.sub.3 is hydrogen, carboxy or sulfo, R.sub.4 is carboxy or sulfo, G is an unsubstituted or substituted 1,4-phenylene group or an unsubstituted or substituted 1,4-naphthylene group, and wherein either R.sub.5 and R.sub.6 together are an additional bond and L is an oxygen or sulfur atom or wherein R.sub.5 is hydrogen, R.sub.6 is halomethyl and L is an oxygen atom, and salts thereof, to the use of compounds I and their salts, to a process for the preparation of compounds I and their salts, to starting materials used in that preparation process, and salts thereof, to a process for the preparation of those starting materials and their salts, to a device in which the compounds I and their salts are used, and to a process in which that device is used.
    Type: Grant
    Filed: September 11, 1991
    Date of Patent: July 20, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Jui Y. Chang
  • Patent number: 5210188
    Abstract: 1. Dyestuffs for cyclic or straight polyfluoropolyoxyalkylenes, of general formula:Q[B--(A).sub.s ].sub.t (III)or[(Q).sub.s --B].sub.2 A (IV)where:Q=an organic group containing a chromophore group, free from free or salified sulphonic and/or carboxylic groups, and/or sulphon-amidic groups;A=a perfluorooxyalkylene chain, which is monovalent in formula (II) and divalent in formula (III);B=an organic at least divalent group;s, t=1 or 2, respectively.2. Compositions comprising cyclic or straight polyfluoropolyoxyalkylenes and at least a dyestuff of formula (III) or (IV) dissolved therein.
    Type: Grant
    Filed: February 11, 1992
    Date of Patent: May 11, 1993
    Assignee: Ausimont S.p.A.
    Inventors: Ezio Strepparola, Piero Gavezotti, Giovanni Gavazzi
  • Patent number: 5175260
    Abstract: Disazo dyes suitable for preparing inks have the formula ##STR1## where m is 1 or 2,n is 0 or 1,Z.sup.1 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl,Z.sup.2 is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkanoyl, substituted or unsubstituted benzoyl, C.sub.1 -C.sub.4 -alkylsulfonyl, substituted or unsubstituted phenylsulfonyl or a derivatized 1,3,5-triazinyl radical, andD is the radical of a diazo component of the class of the thiazole, thiophene, aminobenzoic acid or phenylenediamine compounds.
    Type: Grant
    Filed: August 8, 1991
    Date of Patent: December 29, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Gunter-Rudolf Schroeder, Udo Mayer
  • 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: 5151505
    Abstract: Compounds of formula ##STR1## wherein a and b are each independently of the other halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, c and d are each independently of the other hydrogen, halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, and R.sup.1 is --CH.sub.3, phenyl, --COOCH.sub.3, --COOC.sub.2 H.sub.5, --NHCO--C.sub.1 -C.sub.4 alkyl or --CONH--C.sub.1 -C.sub.4 alkyl, and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted by a chlorine atom or a --OH group, or are C.sub.7 -C.sub.9 aralkyl, C.sub.5 -C.sub.8 cycloalkyl, phenyl or phenyl which is substituted by 1 to 3 halogen atoms or methyl or methoxy groups, or is a heterocyclic radical of the benzimidazole, benzoxazole, benzthiazole or pyridine series, or R.sup.3 and R.sup.
    Type: Grant
    Filed: November 13, 1990
    Date of Patent: September 29, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Stefan Hari, Georg Cseh
  • Patent number: 5118737
    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;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: June 22, 1990
    Date of Patent: June 2, 1992
    Assignee: Canon Kabushiki Kaisha
    Inventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
  • Patent number: 5091517
    Abstract: The invention relates to novel azo dyes of the formula ##STR1## wherein R.sup.1 is an alkyl radical containing 1 to 12 carbon atoms, which is unsubstituted or substituted by hydroxy, alkoxy, cyano or phenyl, or is an aryl radical selected from the group consisting of phenyl, 1-naphthyl, 2-naphthyl, 2-pyridyl, 4-pyridyl, 2-pyrimidinyl and 2-thienyl, these radicals being unsubstituted or substituted by halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, cyano, --NHR.sup.3, --NH--C.sub.2 -C.sub.6 alkanoyl,--NH--benzoyl, phenoxy, COOR.sup.3, --CONHR.sup.3, phenyl, sulfo or C.sub.1 -C.sub.4 alkylsulfone,R.sup.2 is hydrogen or a radical as defined for R.sup.1,R.sup.3 is hydrogen, C.sub.1 -C.sub.6 alkyl, which is unsubstituted or substituted by hydroxy, alkoxy, cyano or phenyl, or phenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, cyano, --NH--C.sub.2 -C.sub.6 alkanoyl, --NH--benzoyl, phenoxy, phenyl, sulfo or C.sub.1 -C.sub.
    Type: Grant
    Filed: November 6, 1990
    Date of Patent: February 25, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Naef
  • Patent number: 5071968
    Abstract: Azo dyes of the formula ##STR1## where D is a diazo component, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently of the others hydrogen or substituted or unsubstituted C.sub.1 -C.sub.8 alkyl, and n is 1,2,3,4 or 5, produce dyeings of good fastness properties on nitrogen-containing or hydroxyl-containing fibre materials.
    Type: Grant
    Filed: March 5, 1990
    Date of Patent: December 10, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Harald Walter
  • Patent number: 5053495
    Abstract: A dye which, in the free acid form, has the formula ##STR1## wherein W is COOHX is selected from H, COOH, SO.sub.3 H, halo, hydroxy, nitro, cyano, C.sub.1-6 -alkyl, C.sub.1-6 -alkoxy and C.sub.1-6 -acylamino;Y is H, COOH or SO.sub.3 H;Z is H, COOH or SO.sub.3 H;R & R.sup.1 are each independently H or C.sub.1-6 -alkyl substituted by 0, 1 or 2 --COOR.sup.2 groups; andR.sup.2 is H or C.sub.1-6 -alkyl;provided that there are at least two COOH groups and that the number of COOH groups is equal to or greater than the number of SO.sub.3 H groups.The dye is adapted for the preparation of inks for use in ink jet printing in which it displays high water-fastness on paper.
    Type: Grant
    Filed: August 24, 1989
    Date of Patent: October 1, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: David Greenwood, Nigel Hughes, Ronald W. Kenyon, Suraj L. Hindagolla
  • Patent number: RE35359
    Abstract: Compounds of formula ##STR1## wherein a and b are each independently of the other halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, c and d are each independently of the other hydrogen, halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, and R.sup.1 is --CH.sub.3, phenyl, --COOCH.sub.3, --COOC.sub.2 H.sub.5, --NHCO--C.sub.1 --C.sub.4 alkyl or --CONH--C.sub.1 -C.sub.4 alkyl, and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted by a chlorine atom or a --OH group, or are C.sub.7 -C.sub.9 aralkyl, C.sub.6 -C.sub.8 cycloalkyl, phenyl or phenyl which is substituted by 1 to 3 halogen atoms or methyl or methoxy groups, or is a heterocyclic radical of the benzimidazole, benzoxazole, benzthiazole or pyridine series, or R.sup.3 and R.sup.
    Type: Grant
    Filed: September 26, 1994
    Date of Patent: October 22, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Stefan Hari, Georg Cseh