Sulfonic Acid Group Bonded Directly To The Bicyclo Ring System (-(o=)s(=o) Oh, Wherein H Of The -oh May Be Replaced By The Ammonium Ion Or A Group Ia Or Iia Light Metal) Patents (Class 534/837)
  • Patent number: 7446184
    Abstract: A compound of Formula (1) and salts thereof: wherein: Q is an optionally substituted aryl ring; Y is CO2H, SO3H or PO3H2; R and X are substituents; m is 0 to 3; n is 0 to 6; and q is 0 to 6. Also compositions comprising these compounds, ink-jet inks, an ink jet process and an ink-jet cartridge.
    Type: Grant
    Filed: December 6, 2004
    Date of Patent: November 4, 2008
    Assignee: Fujifilm Imaging Colorants Limited
    Inventors: Clive Edwin Foster, David Schofield, Julie Ann Downey, Neil Burnham, Philip John Double, Roy Bradbury
  • Patent number: 6143062
    Abstract: Are disclosed disazo compounds represented by the general formula (1): ##STR1## wherein A represents a phenylene or naphthylene group which may be optionally substituted; each of R.sup.1 and R.sup.2 represent independently a hydrogen atom, an alkyl group or a phenyl group which may be optionally substituted; and m is 1 or 2. The compounds are highly water-soluble and are stable to long term storage. Ink compositions comprising the compounds of the invention can produce a printed image with full depth of shade and are excellent in resistance to water.
    Type: Grant
    Filed: December 21, 1998
    Date of Patent: November 7, 2000
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Takashi Miyazawa, Toru Tabei, Isao Yamaguchi, Yasuo Shirasaki, Junko Yoshioka
  • Patent number: 5989326
    Abstract: Disazo dyes formula (VIII) ##STR1## or of formula (IX) ##STR2## Where A, R.sub.1, R.sub.2, n and M are as defined in the specification are excellent dyes for ink jet printing.
    Type: Grant
    Filed: February 3, 1998
    Date of Patent: November 23, 1999
    Assignee: Ilford Imaging Switzerland GmbH
    Inventor: Heinz Peter
  • Patent number: 5882392
    Abstract: A dye of Formula (1) and salts thereof: ##STR1## in which R is H, --NHC.sub.1-4 -alkylN(C.sub.1-4 -alkyl).sub.2 or ##STR2## R.sub.1 and R.sub.2 each independently is H, optionally substituted C.sub.1-4 -alkyl or optionally substituted aryl;R.sub.3 is C.sub.1-4 -alkyl;R.sub.4 is C.sub.1-4 -alkyl or OC.sub.1-4 -alkyl;R.sub.5 is H;R.sub.6 is COOH; andn is 1, 2 or 3.The dyes are useful for preparing ink jet printer inks.
    Type: Grant
    Filed: October 9, 1997
    Date of Patent: March 16, 1999
    Assignee: Zeneca Limited
    Inventors: Peter Gregory, Prahalad Manibhai Mistry, Roy Bradbury, Paul Wight
  • Patent number: 5663309
    Abstract: Azo dyes of the formula ##STR1## in which R.sub.1 is hydrogen or substituted or unsubstituted phenylamino,R.sub.2 is hydrogen, amino or N-mono- or N,N-di-C.sub.1 -C.sub.4 alkylamino,R.sub.3 is hydrogen or hydroxyl,R.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkanoylamino, ureido or halogen andK is as defined in claim 1,the azo dyes of the formula (1) comprising at least one and not more than two sulfo groups,are particularly suitable for dyeing or printing cellulosic fibre materials or naturally occurring or synthetic polyamide fibre materials with a high dyeing yield, and give dyeings and prints with good fastness properties.
    Type: Grant
    Filed: December 5, 1995
    Date of Patent: September 2, 1997
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Hurter
  • Patent number: 5647897
    Abstract: An ink composition for ink jet recording is provided which can satisfy property requirements of quality of print, drying property of print, clogging resistance, water resistance, storage stability, and nonattacking on members constituting an ink passage, such as a printing head. The ink composition for ink jet recording comprises a dye represented by the following formula (I), glycerin, pyrrolidone, a monohydric lower alcohol, a tri(hydroxyalkyl)amine, and water: ##STR1## wherein R.sup.1 represents phenyl or naphthyl substituted by a group selected from hydroxyl, --NH.sub.2, --SO.sub.3 M and --COOM, R.sup.2 represents carboxyalkyl, alkoxyalkyl, phenyl, or alkanoyl, R.sup.3, R.sup.4, and R.sup.5 represent hydrogen or --SO.sub.3 M.
    Type: Grant
    Filed: October 31, 1995
    Date of Patent: July 15, 1997
    Assignee: Seiko Epson Corporation
    Inventors: Yasuhiro Ouki, Miharu Kanaya, Hiroko Hayashi, Kiyohiko Takemoto, Masaaki Itano
  • Patent number: 5510468
    Abstract: There are described benzophenoneazo dyes of the formula ##STR1## where the ring A can be benzofused and a benzofused ring A can be overbridges,m is 1 or 2,K is the radical of a coupling component,Y is hydrogen or arylazo,one of the two radicals X.sup.1 and X.sup.2 is hydrogen and the other is hydroxysulfonyl,R.sup.1, R.sup.2 and R.sup.3 are independently of the others hydrogen, halogen, C.sub.1 -C.sub.12 -alkyl, cyclohexyl, phenyl, 2-hydroxy-ethylsulfonyl or C.sub.1 -C.sub.4 -alkoxy or, when m is 1 and Y is hydrogen, one of these substituents can also be the radical of the formula ##STR2## where L.sup.1 is a chemical bond or a bridge member, and X.sup.1, X.sup.2, R.sup.4, K and the ring A are each as defined above, andR.sup.4 is hydrogen, halogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: July 27, 1994
    Date of Patent: April 23, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Gunther Lamm, Helmut Reichelt, Ortwin Schaffer
  • Patent number: 5380859
    Abstract: There are described benzophenoneazo dyes of the formula ##STR1## where the ring A can be benzofused and a benzofused ring A can be overbridged,m is 1 or 2,K is the radical of a coupling component,Y is hydrogen or arylazo,one of the two radicals X.sup.1 and X.sup.2 is hydrogen and the other is hydroxysulfonyl,R.sup.1, R.sup.2 and R.sup.3 are independently of the others hydrogen, halogen, C.sub.1 -C.sub.12 -alkyl, cyclohexyl, phenyl, 2-hydroxyethylsulfonyl or C.sub.1 -C.sub.4 -alkoxy or, when m is 1 and Y is hydrogen, one of these substituents can also be the radical of the formula ##STR2## where L.sup.1 is a chemical bond or a bridge member, andX.sup.1, X.sup.2, R.sup.4, K and the ring A are each as defined above, andR.sup.4 is hydrogen, halogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: July 16, 1993
    Date of Patent: January 10, 1995
    Assignee: Basf Aktiengesellschaft
    Inventors: Gunther Lamm, Helmut Beichelt, Ortwin Schaffer
  • 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: 5332806
    Abstract: Azo dyes of the formula ##STR1## where A and B are each independently of the other substituted or unsubstituted phenyl or naphthyl and X is --N(R.sub.1)--SO.sub.2 --, --O--SO.sub.2 -- or --SO.sub.2 --N(R.sub.1)--, where R.sub.1 is hydrogen or C.sub.1 -C.sub.8 alkyl, produce very fast dyeings on nitrogen-containing or hydroxyl-containing fibre materials, paper or leather.
    Type: Grant
    Filed: December 10, 1992
    Date of Patent: July 26, 1994
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Hurter
  • 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: 5203912
    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: June 24, 1991
    Date of Patent: April 20, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: David Greenwood, Nigel Hughes, Ronald W. Kenyon, Suraj L. Hindagolla
  • Patent number: 5198022
    Abstract: A alkali-soluble dye for a waterfast ink having structural formula as follows: ##STR1## and an ink containing the dye dissolved in water. Printing from the ink is insoluble below pH 6.0; is an intense black at low concentration; and remains black on acid papers. The aqueous inks are stable and exhibit good printhead nozzle maintenance.
    Type: Grant
    Filed: January 17, 1992
    Date of Patent: March 30, 1993
    Assignee: Lexmark International, Inc.
    Inventors: Rodney O. Aulick, Bradley L. Beach, Donald L. Elbert, Terence E. Franey, James F. Feeman, John M. Olson, Allen C. Sanders, Robert L. Vollmer
  • 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: 5062893
    Abstract: Inks are provided comprising (a) at least two dyes corresponding to the formula ##STR1## wherein W is COOH,X is H, or COOH,Y is H, COOH, or SO.sub.3 H,Z is H, COOH, or SO.sub.3 H, andR is H, CH.sub.2 COOH, or CH.sub.2 CH.sub.2 COOH;with the proviso 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, and (b) a solvent which may be water or a mixture of water and a water-soluble organic solvent provide excellent waterfast prints on paper. The inks preferably have a pH from about 7 to about 9.5. Also preferably, a phosphate is added to reduce kogation and a metal chelating agent is added to further reduce nozzle clogging.
    Type: Grant
    Filed: June 22, 1990
    Date of Patent: November 5, 1991
    Assignee: Hewlett-Packard Company
    Inventors: Raymond J. Adamic, Palitha Wickramanayake, Suraj L. Hindagolla, Garold E. Radke, David J. Halko
  • Patent number: 4963189
    Abstract: Inks are provided comprising (a) a dye corresponding to the formula ##STR1## wherein W is COOH,X is H, or COOH,Y is H, COOH, or SO.sub.3 H,Z is H, COOH, or SO.sub.3 H, andR is H, CH.sub.2 COOH, or CH.sub.2 CH.sub.2 COOH;with the proviso 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 groups, and (b) a solvent which may be water or a mixture of water and a water-soluble organic solvent provide excellent waterfast prints on paper. The inks preferably have a pH from about 7 to about 9.5.
    Type: Grant
    Filed: August 24, 1989
    Date of Patent: October 16, 1990
    Assignee: Hewlett-Packard Company
    Inventor: Suraj L. Hindagolla
  • Patent number: 4841037
    Abstract: A naphthalene trisazo compound represented by the general formula (I) or (II): ##STR1## wherein A and B each represents a substituted or unsubstituted benzene or naphthalene ring; m represents zero or 1; and M represents an alkali metal atom, ammonium or H.Am (wherein Am represents an amine); or ##STR2## wherein X represents a hydrogen atom, a lower alkyl group, a phenyl group or a phenyl group substituted by --SO.sub.3 M; m represents zero or 1; M represents an alkali metal atom, ammonium or H.Am (wherein Am represents an amine); A, B and C each represents a substituted or an unsubstituted benzene or naphthalene ring, provided that B and C do not represent a naphthalene ring at the same time. A recording liquid containing these compounds is suitable for use in an ink-jet recording system.
    Type: Grant
    Filed: June 10, 1986
    Date of Patent: June 20, 1989
    Assignees: Canon Kabushiki Kaisha, Mitsubishi Chemical Industries Limited
    Inventors: Tokuya Ohta, Masatsune Kobayashi, Yuko Suga, Konoe Miura, Hiroshi Takimoto, Tomio Yoneyama
  • Patent number: 4772687
    Abstract: Metal complex dyestuffs which in the form of the free acid correspond to the formula ##STR1## in which the substituents have the meaning given in the description are, depending on the meanings of the substituents, suitable for use as reactive dyestuffs for cotton, wool or polyamide, as direct dyestuffs for cotton or as pigment dyestuffs. Dyeings are obtained which have good fastness properties, in particular good wet-, light- and chlorine fastness.
    Type: Grant
    Filed: May 1, 1986
    Date of Patent: September 20, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hermann Henk
  • 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: 4544739
    Abstract: Chromium complex dyes which, in the form of the free acid, have the formula ##STR1## wherein Z is hydrogen, nitro, chlorine or naphthylazo or phenylazo, wherein naphthyl or phenyl is unsubstituted or substituted by nitro, chlorine, bromine, C.sub.1-5 -alkyl or C.sub.1-5 -alkoxy, A is naphthyl or phenyl containing the oxygen atom in o-position to the azomethine and wherein naphthyl or phenyl is unsubstituted or substituted by C.sub.1-5 -alkyl, halogen or naphthylazo or phenylazo wherein naphthyl or phenyl is unsubstituted or substituted by nitro, chlorine, bromine, C.sub.1-5 -alkyl or C.sub.1-5 -alkoxy, D is sulfophenyl which is unsubstituted or substituted by nitro or chlorine, or sulfonaphthyl which is unsubstituted or substituted by nitro, and is bonded to the azo group in the ortho-position to the oxygen atom and R is chloroacetyl, bromoacetyl, .alpha.-chloroacryloyl, .alpha.-bromoacryloyl, .alpha.,.beta.-dichloropropionyl, .alpha.,.beta.
    Type: Grant
    Filed: September 28, 1982
    Date of Patent: October 1, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans U. Schutz, Arthur Buhler