Hydroxy Bonded Directly To A Bicyclo Ring System (h Of Hydroxy May Be Replaced By The Ammonium Ion Or A Group Ia Or Iia Light Metal) Patents (Class 534/815)
  • Patent number: 8477268
    Abstract: Azo compounds represented by formula (1) (In the formula, R1 represents a lower alkoxy group with a sulfone group. R2-R5 each independently represents a hydrogen atom, lower alkyl group or lower alkoxy group. X is an optionally substituted amino group, optionally substituted benzoylamino group, optionally substituted phenylamino group, optionally substituted phenyl azo group or optionally substituted naphthotriazole group. m represents 1 or 2 and n represents 0 or 1.) and salts thereof.
    Type: Grant
    Filed: May 19, 2009
    Date of Patent: July 2, 2013
    Assignees: Nippon Kayaku Kabushiki Kaisha, Polatechno Co., Ltd.
    Inventors: Takuto Nishiguchi, Hiroaki Ohno, Takahiro Higeta, Yuichi Sadamitsu
  • Patent number: 8232375
    Abstract: Disclosed is an azo compound represented by the formula (1) or (2) or a salt thereof. The azo compound or the salt thereof has an excellent light-polarizing property, and is extremely useful as a dichroic dye for use in a polarizing plate that shows less color leakage in a visible light range or a polarizing plate for a liquid crystal projector comprising the aforementioned polarizing plate. (1) (2) wherein R1 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a hydroxyl group, a sulfonate group or a carboxyl group; R2 to R5 independently represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or an acetylamino group; X represents 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; m represents a numeral number of 1 or 2; and n represents a numeral number of 0 or 1.
    Type: Grant
    Filed: October 30, 2008
    Date of Patent: July 31, 2012
    Assignees: Nippon Kayaku Kabushiki Kaisha, Polatechno Co., Ltd.
    Inventors: Takahiro Higeta, Hiroaki Ohno, Yuichi Sadamitsu
  • Publication number: 20110164208
    Abstract: Azo compounds represented by formula (1) (In the formula, R1 represents a lower alkoxy group with a sulfone group. R2-R5 each independently represents a hydrogen atom, lower alkyl group or lower alkoxy group. X is an optionally substituted amino group, optionally substituted benzoylamino group, optionally substituted phenylamino group, optionally substituted phenyl azo group or optionally substituted naphthotriazole group. m represents 1 or 2 and n represents 0 or 1.) and salts thereof.
    Type: Application
    Filed: May 19, 2009
    Publication date: July 7, 2011
    Applicants: NIPPON KAYAKU KABUSHIKI KAISHA, POLATECHNO CO., LTD.
    Inventors: Takuto Nishiguchi, Hiroaki Ohno, Takahiro Higeta, Yuichi Sadamitsu
  • Patent number: 7960521
    Abstract: To provide a dye capable of forming an anisotropic dye film showing high dichroism and having a high degree of molecular orientation, a composition containing the dye, an anisotropic dye film using the dye and a polarizing element. A trisazo dye, of which the free acid form is represented by the following formula (1), wherein at least one of B1 and D1 has at least one substituent as defined by the following Q1, a dye composition for an anisotropic dye film containing the dye, an anisotropic dye film and a polarizing element using the anisotropic dye film: Q1: an alkyl group or alkoxy group substituted by a hydrogen bond-forming group: wherein A1 is a phenyl group or a naphthyl group, each of B1 and D1 is a phenylene group or a naphthylene group, X1 is an amino group which may be substituted or a hydroxyl group, and m is 0 or 1.
    Type: Grant
    Filed: December 14, 2005
    Date of Patent: June 14, 2011
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hideo Sano, Masami Kadowaki, Ryuichi Hasegawa, Wataru Shimizu
  • Publication number: 20100257678
    Abstract: Disclosed is an azo compound represented by the formula (1) below, a salt thereof, or a copper complex salt compound thereof. (In the formula, R1 and R2 independently represent a hydrogen atom, a sulfonic acid group, a lower alkyl group or a lower alkoxyl group; R3-R6 independently represent a hydrogen atom, a lower alkyl group or a lower alkoxyl group; R7 represents a lower alkyl group or a lower alkoxyl group; and n represents 0 or 1.
    Type: Application
    Filed: June 21, 2007
    Publication date: October 14, 2010
    Inventors: Yuichi Sadamitsu, Takahiro Higeta
  • Publication number: 20090275742
    Abstract: It is to provide a dye for an anisotropic dye film to be formed by a wet system film-forming method, which is achromatic and has high dichroism and a high degree of molecular orientation, an anisotropic dye film containing the dye and a polarizing element employing the film. A dye for an anisotropic dye film to be formed by a wet system film-forming method, of which the free acid form is represented by the following formula (I), a composition for an anisotropic dye film containing the dye, an anisotropic dye film and a polarizing element employing the anisotropic dye film: wherein A11: a (substituted) phenyl group, a (substituted) naphthyl group or a (substituted) aromatic heterocyclic group; B11: a bivalent aromatic hydrocarbon group or aromatic hydrocyclic group; R11, R22: H, OH, a (substituted) alkyl group, a (substituted) phenyl group or a (substituted) acyl group; n?: 1 or 2; m: 0 or 1.
    Type: Application
    Filed: April 4, 2006
    Publication date: November 5, 2009
    Applicant: MITSUBISHI CHEMICAL CORPORATION
    Inventors: Hideo Sano, Tomio Yoneyama, Masaaki Nishimura, Wataru Shimizu, Ryuichi Hasegawa, Masami Kadowaki, Junichi Oizumi
  • Publication number: 20090267031
    Abstract: To provide a dye capable of forming an anisotropic dye film showing high dichroism and having a high degree of molecular orientation, a composition containing the dye, an anisotropic dye film using the dye and a polarizing element. A trisazo dye, of which the free acid form is represented by the following formula (1), wherein at least one of B1 and D1 has at least one substituent as defined by the following Q1, a dye composition for an anisotropic dye film containing the dye, an anisotropic dye film and a polarizing element using the anisotropic dye film: Q1: an alkyl group or alkoxy group substituted by a hydrogen bond-forming group: wherein A1 is a phenyl group or a naphthyl group, each of B1 and D1 is a phenylene group or a naphthylene group, X1 is an amino group which may be substituted or a hydroxyl group, and m is 0 or 1.
    Type: Application
    Filed: December 14, 2005
    Publication date: October 29, 2009
    Applicant: Mitsubishi Chemical Corporation
    Inventors: Hideo Sano, Masami Kadowaki, Ryuichi Hasegawa, Wataru Shimizu
  • Publication number: 20090208713
    Abstract: A compound selected from the group consisting of compounds of Formula (1) and compounds of Formula (2) or a salt thereof: wherein: A is an optionally substituted alpha naphthyl group of formula X, wherein * is the point of attachment to the azo group in Formula (1) or (2); B is optionally substituted phenylene or naphthylene; n is 0 or 1; and D is an optionally substituted pyrazolyl group. The compound is useful in an ink for ink jet printing. Also provided are printing processes, ink compositions and ink-jet cartridges for use in an ink-jet printer and substrates printed using an ink-jet printer.
    Type: Application
    Filed: April 27, 2007
    Publication date: August 20, 2009
    Inventors: Prahalad Manibhai Mistry, Roy Bradbury, Lynn Patricia Bradbury
  • Publication number: 20090041939
    Abstract: A compound selected from the group consisting of compounds of Formula (1) and compounds of Formula (2) or a salt thereof: wherein: A is a beta naphthyl group of formula X, wherein * is the point of attachment to the azo group in Formula (1) or (2) p and q are each independently 0, 1 or 2 and the sum of p+q is not zero; B is optionally substituted phenylene or naphthylene; n is 0 or 1; and D is an optionally substituted pyrazolyl group. The compound or salt is useful in an ink for ink jet printing. Also provided are printing processes, ink compositions and ink-jet cartridges for use in an ink-jet printer and substrates printed using an ink-jet printer.
    Type: Application
    Filed: April 27, 2007
    Publication date: February 12, 2009
    Inventor: Prahalad Manibhai Mistry
  • Patent number: 7326288
    Abstract: [PROBLEMS] To provide: a black compound which is for use in ink-jet recording or writing utensils, is excellent in ozone resistance, light resistance, moisture resistance, and color rendering, and gives a recording fluid having satisfactory storage stability; and an ink composition containing the compound. [MEANS FOR SOLVING PROBLEMS] The black compound is a trisazo compound represented by the following formula (1) or a salt thereof. (1) [In the formula (1), R1 and R2 each independently represents hydrogen, carboxy, sulfo, hydroxy, a C1-4 alkyl, C1-4 alkoxy, or sulfo group optionally substituted by C1-4 alkoxy, an optionally carboxylated C1-4 alkoxy group, etc.; and A represents phenyl or naphthyl (provided that the phenyl and naphthyl groups may be substituted by halogeno, carboxy, sulfo, sulfamonyl optionally substituted by alkyl or phenyl, nitro, etc.).
    Type: Grant
    Filed: November 26, 2004
    Date of Patent: February 5, 2008
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Takahiko Matsui, Hiroaki Ohno, Takashi Yoneda, Yoshiaki Kawaida, Yasuo Shirasaki
  • Patent number: 7056376
    Abstract: A process for printing an image on a substrate comprising applying thereto a composition comprising a liquid medium and a compound of Formula (1): T-Q-N?N-L-T??Formula (1) wherein: each T independently is an azo group; Q is an optionally substituted, optionally metallised 1,8-dihydroxynaphthyl group; and L is a divalent organic linker group. Also claimed are compositions and dyes.
    Type: Grant
    Filed: April 11, 2003
    Date of Patent: June 6, 2006
    Assignee: Avecia Limited
    Inventors: Ajay Haridas Popat, Alan Dickinson, Maria Soteri Hadjisoteriou, Neil James Thompson, Paul Wight, Peter Gregory, Roy Bradbury, Philip John Double, Thomas Paul
  • 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: 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: 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: 5739296
    Abstract: Polarizing coatings are formed from dyestuffs which provide a stable liquid crystalline phase in a wide range of concentrations, temperatures and pH-values. Particles formed by aggregates of the liquid crystal molecules are oriented in a predetermined direction to polarize light. The stability of the liquid crystalline state allows orienting the particles by mechanical forces such as a shearing force applied when the liquid crystal (10) is spread on a support surface (20) by a knife-like doctor (90) or a tension deformation force acting on the meniscus of the liquid crystal deposited between two surfaces (20, 30) as the surfaces are peeled off one another. As a result, the polarizing coatings are formed in some embodiments by simple methods. In some embodiments, the polarizing coatings have a high lightfastness, a high thermal stability, and a high dichroic ratio.
    Type: Grant
    Filed: November 20, 1995
    Date of Patent: April 14, 1998
    Assignee: Russian Technology Group
    Inventors: Khan Ir Gvon, Yuri A. Bobrov, Victor A. Bykov, Leonid Y. Ignatov, Tatiana D. Ivanova, Sergei I. Popov, Elena Y. Shishkina, Georgiy N. Vorozhtsov
  • Patent number: 5616174
    Abstract: An ink composition is provided which enables high-quality recording on plain paper and can record an image having excellent water resistance. The ink composition comprises a dye represented by the following formula (I): ##STR1## wherein M represents an unsubstituted or substituted ammonium, R.sup.1 represents COOM, R.sup.2 represents --P(=O)n--(OM).sub.2, where n is 0 or 1, R.sup.3 represents SO.sub.3 M, R.sup.4 and R.sup.5 independently represent H, an alkyl group, or an alkoxyl group, R.sup.6 represents H, a phenyl group which may be substituted, an alkylcarbonyl group, or an alkyl group which may be substituted with a hydroxyl or alkoxyl group, and m is 0 or 1.
    Type: Grant
    Filed: December 4, 1995
    Date of Patent: April 1, 1997
    Assignee: Seiko Epson Corporation
    Inventors: Miharu Kanaya, Akio Owatari, Junko Takatsuna, Masahiro Yatake, Hiroko Hayashi, Takashi Ono, Yoshihiro Sawatari, Tatsuya Yagyu
  • Patent number: 5494507
    Abstract: A dye having a representative formula as follows and an ink providing waterfast printing having the dye, in which a surfactant is not essential: ##STR1##
    Type: Grant
    Filed: December 19, 1994
    Date of Patent: February 27, 1996
    Assignee: Lexmark International, Inc.
    Inventors: Bradley L. Beach, James F. Feeman, Ann M. Piekunka, Allen C. Sanders
  • Patent number: 5488101
    Abstract: Herein is provided a trisazo compound represented by formula (I) in the free acid form: ##STR1## wherein Q.sub.1 is an unsubstituted or substituted phenylene or naphthylene group, Q.sub.2 is an unsubstituted or substituted phenyl or naphthyl group, Z is --SO.sub.2 CH.sub.2 CH.sub.2 OH or --SO.sub.2 CH.sub.2 CH.sub.2 SO.sub.3 H group, and L is 0 or 1. The trisazo compound provided herein is excellent in solubility and gives deep colored dyed product or image when used in dyeing or printing, so that it is useful as a dye and an ink. Herein are also provided a method for dyeing fiber materials, paper or leather by using said trisazo compound, and an ink containing said trisazo compound.
    Type: Grant
    Filed: June 5, 1992
    Date of Patent: January 30, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazuya Ogino, Kingo Akahori, Naoki Harada, Yutaka Kayane, Hideo Kawashita, Mituhiro Ohta
  • Patent number: 5486601
    Abstract: Disclosed is a trisazo dye represented by the formula: ##STR1## wherein R.sup.1 and R.sup.2 independently represent a substituted amino group which is substituted with hydrogen, a hydroxyl group, a carboxyl group, an amino group, an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group or an acyl group, or an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms; and R.sup.3 is hydrogen, an alkyl or alkoxy group having 1 to 6 carbon atoms; provided that R.sup.1 and R.sup.2 are not amino groups or substituted amino groups simultaneously.A process for producing the trisazo dye and an aqueous ink composition containing the trisazo dye are also disclosed.
    Type: Grant
    Filed: September 28, 1994
    Date of Patent: January 23, 1996
    Assignee: Orient Chemical Industries, Ltd.
    Inventors: Tatsuya Yagyu, Takashi Ono
  • Patent number: 5446135
    Abstract: Dyes having the specific structural formula (1) set out below, their copper salt dyes, water-soluble azo dyes containing the dyes or the copper salt dyes, and polarizing films containing the water-soluble azo dyes: ##STR1## wherein A means a benzene or naphthalene ring having a sulfone group or a base thereof, Y and Z individually denote a group of the following formula (a); ##STR2## wherein R.sup.2 is a hydrogen atom, a methyl group, a methoxyl group or an ethoxyl group and R.sup.3 is a methyl, methoxyl or ethoxyl group,R.sup.1 represents an amino, C.sub.1-4 alkylamino, C.sub.2-4 alkylcarboxyamino, benzoylamino or phenylamino group bonded to the 6 or 7 position of the naphthalene ring, and X denotes a hydrogen, sodium, potassium or lithium atom, with the proviso that Y and Z are different but, when both R.sup.2 s are hydrogen atoms and both R.sup.3 s are methoxyl groups, Y and Z may be the same.
    Type: Grant
    Filed: March 14, 1994
    Date of Patent: August 29, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Tsutami Misawa, Akira Ogiso, Rihoko Imai, Hisato Itoh
  • Patent number: 5423906
    Abstract: A compound of Formula (1) or salt thereof: ##STR1## wherein: R.sup.1 is H, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, CO.sub.2 H, SO.sub.3 H or --NR.sup.3 R.sup.4 ;R.sup.2 is H, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, CO.sub.2 H or SO.sub.3 H;R.sup.3 and R.sup.4 are each independently H, C.sub.1-18 -alkyl or R.sup.3 and R.sup.4, together with the nitrogen atom to which they are attached, form an optionally substituted 5- or 6-membered ring;W is --OH and X is --NH.sub.2, or W is --NH.sub.2 and X is --OH; andY and Z are each independently --OH or --NR.sup.3 R.sup.4.The compound is suitable for use as a black component of ink jet printing inks.
    Type: Grant
    Filed: August 19, 1993
    Date of Patent: June 13, 1995
    Assignee: Zeneca Limited
    Inventors: Peter Gregory, Prahalad M. Mistry
  • Patent number: 5370730
    Abstract: Dye compositions and aqueous inks derived therefrom, especially suitable for use in ink jet printing in which the dye composition contains (a) one or more dyes which, in the free acid form, are of Formula (1): ##STR1## wherein W is H or COOH;X is H or COOH;Y is H or COOH;U & Z are each independently H, COOH or SO.sub.3 H; andV is H or SO.sub.3 H;and (b) one or both dyes which in the free acid form is of Formula (2): ##STR2## wherein A is NH.sub.2 and B is OH; orA is OH and B is NH.sub.2.
    Type: Grant
    Filed: April 12, 1993
    Date of Patent: December 6, 1994
    Assignee: Zeneca Limited
    Inventors: Peter Gregory, Ronald W. Kenyon, John E. Presgrave
  • 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: 5340504
    Abstract: The invention relates to light-polarizing films based on water-soluble organic polymers, more particularly polyvinyl alcohol (PVAL), which contain one or more dichroic bis-, tris- or tetrakis-azo dyes.
    Type: Grant
    Filed: February 23, 1993
    Date of Patent: August 23, 1994
    Assignee: Bayer AG
    Inventor: Uwe Claussen
  • 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: 5318856
    Abstract: Dyes having the specific structural formula (1) set out below, their copper salt dyes, water-soluble azo dyes containing the dyes or the copper salt dyes, and polarizing films containing the water-soluble azo dyes: ##STR1## wherein A means a benzene or naphthalene ring having a sulfone group or a base thereof, Y and Z individually denote a group of the following formula (a): ##STR2## wherein R.sup.2 is a hydrogen atom, a methyl group, a methoxyl group or an ethoxyl group and R.sup.3 is a methyl, methoxyl or ethoxyl group, R.sup.1 represents an amino, C.sub.1-4 alkylamino, C.sub.2-4 alkylcarboxyamino, benzoylamino or phenylamino group bonded to the 6 or 7 position of the naphthalene ring, and X denotes a hydrogen, sodium, potassium or lithium atom, with the proviso that Y and Z are different but, when both R.sup.2 s are hydrogen atoms and both R.sup.3 s are methoxyl groups, Y and Z may be the same.
    Type: Grant
    Filed: December 24, 1992
    Date of Patent: June 7, 1994
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Tsutami Misawa, Akira Ogiso, Rihoko Imai, Hisato Itoh
  • Patent number: 5256194
    Abstract: A recording liquid containing a dye, glycerine, an aliphatic monohydric alcohol and water. The dye is a mixture of C.I. Food Black 2 and at least one compound selected from compounds which are represented by the following general formulas [I] and [II]: ##STR1## [where Q1 is a phenyl group or a naphthyl group which are substituted by a lower alkyl carbonylamino group and a lower alkoxy group or a naphthyl group substituted by a SO.sub.3 M group, Q2 is a naphthyl group substituted by a SO.sub.3 M group or a phenyl group substituted by a lower alkoxy group, Q3 is a phenyl group, a naphthyl group, or a phenyl group or a naphthyl group which are substituted by a SO.sub.3 M group, R.sub.1 and R.sub.2 are each a lower alkyl group, a lower alkoxy group or a lower alkyl carbonylamino group, R.sub.3 is a hydrogen or a phenyl group substituted by a SO.sub.3 M group, n is 0 or 1, and M is an alkaline metal or an ammonium cation.
    Type: Grant
    Filed: September 2, 1992
    Date of Patent: October 26, 1993
    Assignee: Canon Kabushiki Kaisha
    Inventors: Osamu Nishiwaki, Kazuo Iwata, Shinichi Tochihara, Hitoshi Sugimoto
  • Patent number: 5213614
    Abstract: An ink comprising: water, a water soluble organic solvent, and a colorant represented by the following general formula (I): ##STR1## wherein Q1 is a substituted phenyl group; Q2 is a substituted or unsubstituted p-phenylene or a substituted or unsubstituted 1,4-naphtylene group; Q3 is a substituted phenyl group; M is an alkali metal, ammonium or an organic ammonium; and n is 0 or 1, and wherein said colorant has at least a sulfone group and a carboxyl group and the number of said sulfone groups is not greater than the number of said carboxyl groups. Such an ink may be used for an ink jet recording.
    Type: Grant
    Filed: January 17, 1992
    Date of Patent: May 25, 1993
    Assignee: Canon Kabushiki Kaisha
    Inventors: Tsuyoshi Eida, Mayumi Yamamoto, Takao Yamamoto
  • 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: 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: 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: 5167703
    Abstract: Provided is an ink comprising at least water, a water-soluble organic solvent, and a dye, the dye comprising a compound represented by the general formula (I): ##STR1## wherein R.sub.1, R.sub.2, and R.sub.3 are respectively hydrogen or SO.sub.3 M; R.sub.4 is hydrogen, OCH.sub.3, NH.sub.2, NHCONH.sub.2, or SO.sub.3 M; R.sub.5 is hydrogen or SO.sub.3 M; R.sub.6 is hydrogen or NH.sub.2 ; R.sub.7 is hydrogen, CH.sub.3, or OCH.sub.3 ; R.sub.8 is hydrogen, COOM, or SO.sub.3 M; R.sub.5 is hydrogen and R.sub.8 is COOM when both of R.sub.4 and R.sub.6 are respectively NH.sub.2 ; M is an alkali metal, ammonium, or organic ammonium; and m is 0 or 1, or a compound represented by the general formula (II): ##STR2## wherein R.sub.1 is hydrogen, CH.sub.3, COOM, or SO.sub.3 M; R.sub.2 is hydrogen, CH.sub.3, or COOM; R.sub.3 is hydrogen, chlorine, COOM, or SO.sub.3 M; R.sub.4 is hydrogen, OCH.sub.3, NH.sub.2, NHCONH.sub.2, or SO.sub.3 M; R.sub.5 is hydrogen or SO.sub.3 M; R.sub.6 is hydrogen or NH.sub.2 ; R.sub.
    Type: Grant
    Filed: November 27, 1991
    Date of Patent: December 1, 1992
    Assignee: Canon Kabushiki Kaisha
    Inventors: Tsuyoshi Eida, Mayumi Yamamoto, Takao Yamamoto
  • Patent number: 5127946
    Abstract: Provided is an ink containing a recording agent and a liquid medium for dissolution or dispersion thereof, said ink comprising, as the recording agent, a compound represented by the general formula (A) ##STR1## where n is 0 or 1; R.sub.1, R.sub.2, and R.sub.3 are respectively a substituent selected from the group consisting of hydrogen, methyl, methoxy, hydroxy, amino, acetylamino, and sulfonic acid; and M is an alkali metal, ammonium, or an organic ammonium.
    Type: Grant
    Filed: January 23, 1991
    Date of Patent: July 7, 1992
    Assignee: Canon Kabushiki Kaisha
    Inventors: Tsuyoshi Eida, Takao Yamamoto, Mayumi Yamamoto
  • Patent number: 5125969
    Abstract: A recording liquid containing a dye, glycerine, an aliphatic monohydric alcohol and water. The dye is a mixture of C.I. Food Black 2 and at least one compound selected from compounds which are represented by the following general formulas [I] and [II]: ##STR1## where Q1 is a phenyl group or a naphthyl group which are substituted by a lower alkyl carbonylamino group and a lower alkoxy group or a naphthyl group substituted by a SO.sub.3 M group, Q2 is a naphthyl group substituted by a SO.sub.3 M group or a phenyl group substituted by a lower alkoxy group, Q3 is a phenyl group, a naphthyl group, or a phenyl group or a naphthyl group which are substituted by a SO.sub.3 M group, R.sub.1 and R.sub.2 are each a lower alkyl group, a lower alkoxy group or a lower alkyl carbonylamino group, R.sub.3 is a hydrogen or a phenyl group substituted by a SO.sub.3 M group, n is 0 or 1, and M is an alkaline metal or an ammonium cation.
    Type: Grant
    Filed: January 17, 1990
    Date of Patent: June 30, 1992
    Assignee: Canon Kabushiki Kaisha
    Inventors: Osamu Nishiwaki, Kazuo Iwata, Shinichi Tochihara, Hitoshi Sugimoto
  • Patent number: 5110917
    Abstract: The present invention relates to water-soluble trisazo dyes of the formula T ##STR1## and process for the preparation thereof and to the use thereof.
    Type: Grant
    Filed: August 5, 1991
    Date of Patent: May 5, 1992
    Assignee: Cassella Aktiengesellschaft
    Inventors: Wolfgang Bauer, Willi Steckelberg, Josef Ritter
  • Patent number: 5049238
    Abstract: A method of dyeing paper utilizing dyes suitable for dyeing paper in blue shades having the formula ##STR1## wherein R is hydrogen, --OH, --OR.sup.1 , --NH.sub.2, NHR.sup.1, --NHCOR.sup.1, --NHSO.sub.2 R.sup.1, --NHCONH.sub.2 or --NHCONHR.sup.1, in which R.sup.1 is unsubstituted alkyl or alkyl substituted by C.sub.1 -C.sub.4 -alkoxy, hydroxy-substituted C.sub.1 -C.sub.4 -alkoxy, phenyl, phenoxy or phenylcarbamoyl, in each instance the phenyl moiety being unsubstituted or substituted by C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxy or phenoxy, R.sup.1 is also unsubstituted phenyl or naphthyl or phenyl or naphthyl which is substituted by sulfo, carboxy, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, nitro, C.sub.1 -C.sub.4 -alkylcarbonylamino or C.sub.1 -C.sub.4 -alkoxycarbonylamino;X, each independently of the other, is hydrogen, unsubstituted alkyl or alkoxy or alkyl or alkoxy which is substituted by C.sub.1 -C.sub.4 -alkoxy, hydroxy-substituted C.sub.1 -C.sub.
    Type: Grant
    Filed: July 19, 1989
    Date of Patent: September 17, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Adolf Kaser
  • 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: 4836827
    Abstract: The compounds of the formula (1) given in claim 1 are suitable for use as dyes for dyeing a wide range of textile and non-textile materials and in particular for dyeing leather and pelts.
    Type: Grant
    Filed: January 29, 1988
    Date of Patent: June 6, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Alois Puntener
  • Patent number: 4804411
    Abstract: A recording liquid comprising a solution of a recording agent is provided. The recording agent has a structure containing a plural number of structural units linked together through a linking group or groups. The structural unit may be a dye residue.
    Type: Grant
    Filed: February 13, 1987
    Date of Patent: February 14, 1989
    Assignee: Canon Kabushiki Kaisha
    Inventors: Tsuyoshi Eida, Yuko Suga, Katsuhiro Shirota
  • Ink
    Patent number: 4767459
    Abstract: An ink for ink-jet printing comprising a solution of C.I. Direct Black 168.
    Type: Grant
    Filed: September 16, 1987
    Date of Patent: August 30, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: David Greenwood, John E. Presgrave
  • Patent number: 4737240
    Abstract: Black trisazo dyes for cellulosic textiles, leather and especially paper having the structure ##STR1## where A is ##STR2## one of B.sub.1 and B.sub.2 is hydrogen and the other is --SO.sub.3 M or a mixture thereof, and M is hydrogen, sodium, potassium, lithium or --HNR.sub.1 R.sub.2 R.sub.3 wherein R.sub.1, R.sub.2 and R.sub.3 represent the same or different substituents selected from hydrogen, lower alkyl and lower hydroxyalkyl, and stable liquid concentrates of these dyes are described.
    Type: Grant
    Filed: June 27, 1986
    Date of Patent: April 12, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Herbert S. Davis, Roy E. Smith, Mortimer Weiser
  • Patent number: 4734489
    Abstract: An azo compound of the formula: ##STR1## wherein R is of the formula: ##STR2## R.sub.1 is hydrogen, methyl or --SO.sub.3 M; R.sub.2 is hydrogen or --SO.sub.3 M; R.sub.2 is hydrogen or --SO.sub.3 M; R.sub.3 is C.sub.4 -C.sub.18 alkyl and M is hydrogen, an alkali metal, ammonium or organic ammonium, provided that when R includes --SO.sub.3 M, R.sub.1 l and R.sub.2 are not --SO.sub.3 M, and when R does not include --SO.sub.3 M, either one of R.sub.1 and R.sub.2 is --SO.sub.3 M, which is useful as a black dyestuff for a solvent type ink composition, particularly for ink jet recording.
    Type: Grant
    Filed: March 27, 1986
    Date of Patent: March 29, 1988
    Assignees: Taoka Chemical Company, Limited, Sumitomo Chemical Company, Limited
    Inventors: Shinjiro Kawasaki, Hideo Kitagawa, Yutaka Nishii, Hideo Kawashita, Minoru Akagi
  • Patent number: 4701525
    Abstract: Compounds of the formula(B--L.sub.m --A--L'--B'.sub.n, (1)in which A is the radical of a bisazo or trisazo dye, L and L' are organic radicals and B and B' are cyclic organic radicals and at least one of the radicals B and B' has spectral absorption in the UV region and one of the radicals B and B' is different from 2,4-dihydroxyphenyl, m is 1 or 2 and n is 0, 1 or 2.The compounds are suitable for use as image dyes in photographic silver dye bleach materials.
    Type: Grant
    Filed: June 2, 1986
    Date of Patent: October 20, 1987
    Assignee: Ciba-Geigy AG
    Inventors: Thomas-Markus Rohr, Jakob Kuhn
  • Patent number: 4600674
    Abstract: Disclosed is an electrophotographic photoconductive material excellent in sensitivity and durability which comprises an electroconductive substrate and, provided thereon, a photosensitive layer containing a trisazo pigment represented by the general formula ##STR1## wherein R's, which may be the same or different, represent each a hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, alkoxyl group, or nitrile group; n is an integer of 1 or 2; and A represents ##STR2## wherein Z represents a group of atoms necessary to complete a substituted or unsubstituted aromatic carbon ring or a substituted or unsubstituted aromatic hetero-ring; X represents a hydrogen atom, an alkyl group, or a group of atoms necessary to complete a substituted or unsubstituted aromatic carbon ring, a substituted or unsubstituted aromatic hetero ring, or a substituted or unsubstituted hetero ring; m is 0 or 1; B represents a group of atoms necessary to complete a substituted or unsubstituted aromatic carbon ring, a subst
    Type: Grant
    Filed: June 24, 1985
    Date of Patent: July 15, 1986
    Assignee: Mitsubishi Paper Mills, Ltd.
    Inventors: Kazuhiro Emoto, Akira Itoh
  • 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: 4591634
    Abstract: Trisazo/azoxy dyestuff mixtures which in the form of free acid correspond to the formula ##STR1## in which R denotes H or optionally substituted alkyl,X and Y denote H, alkyl, alkoxy, halogen, hydroxyl, alkylsulphonyl, optionally mono- or di-alkyl-substituted sulphamyl, carboxyl and carboxyalkoxy andK denotes the radical of a coupling component,are outstandingly suitable for dyeing fibre materials containing hydroxyl groups and fibre materials containing amide groups, such as cotton, natural and synthetic polyamide, paper and leather. They give dyeings having good build-up capacity and good combinability.
    Type: Grant
    Filed: July 15, 1985
    Date of Patent: May 27, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl J. Herd, Horst Nickel
  • 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