Plural Acyclic Chalcogens Bonded Directly To The Hetero Ring At The Two Positions Adjacent To The Ring Nitrogen Patents (Class 534/772)
  • Patent number: 9910196
    Abstract: The present invention provides a dye compound excellent in both chroma and light fastness, an ink, and a resist composition for a color filter. The present invention provides an ink and a resist composition for a color filter, in which each of the ink and the resist composition contains a pyridone azo compound having a specific structure.
    Type: Grant
    Filed: September 24, 2014
    Date of Patent: March 6, 2018
    Assignee: Canon Kabushiki Kaisha
    Inventors: Takeshi Sekiguchi, Shosei Mori, Taichi Shintou, Takeshi Miyazaki
  • Patent number: 9388313
    Abstract: The present invention provides a water-insoluble coloring compound having a high solvent solubility, showing increased brightness and saturation, and being useful for increasing the green gamut and also provides an ink containing the water-insoluble coloring compound. The present invention provides a thermal transfer recording sheet including a coloring material layer formed on a base material from the ink and also provides a color filter resist composition showing an increased green gamut due to the ink.
    Type: Grant
    Filed: January 16, 2013
    Date of Patent: July 12, 2016
    Assignee: Canon Kabushiki Kaisha
    Inventors: Yuko Katsumoto, Shosei Mori, Takeshi Sekiguchi, Taichi Shintou, Takayuki Ujifusa, Takeshi Miyazaki
  • Patent number: 9382426
    Abstract: The present invention provides a water-insoluble coloring compound having excellent light resistance, an ink containing the coloring compound, a thermal transfer recording sheet including a coloring material layer formed on a base material from the ink, and a color filter resist composition containing the ink.
    Type: Grant
    Filed: January 16, 2013
    Date of Patent: July 5, 2016
    Assignee: Canon Kabushiki Kaisha
    Inventors: Takeshi Sekiguchi, Shosei Mori, Taichi Shintou, Yuko Katsumoto, Takayuki Ujifusa, Takeshi Miyazaki
  • Publication number: 20150073132
    Abstract: Disclosed is a method for continuously preparing a water-soluble azo dye by coupling a nebulizer with a pipeline. According to the method, the nebulizer is coupled with a pipeline with an interception tower plate, atomized and mixed reaction liquid flow flows through the pipeline with the interception tower plate, and mixing and reacting are further enhanced through turbulent mixing on the tower plate, so that instant separation of reaction heat generated in an atomizing contact reaction from a reactant is achieved, and normal-temperature rapid continuous production of the water-soluble azo dye is achieved. Fog drops which are atomized by using the nebulizer have small particle diameter and large specific surface area, so that a diazo salt and a coupling component are sprayed separately, move face to face and can be fully contacted, and mixing and reacting speeds are increased.
    Type: Application
    Filed: November 30, 2012
    Publication date: March 12, 2015
    Inventors: Shufen Zhang, Bingtao Tang, Rongwen Lv, Dong Liang
  • Publication number: 20140370207
    Abstract: The present invention provides a water-insoluble coloring compound having excellent light resistance, an ink containing the coloring compound, a thermal transfer recording sheet including a coloring material layer formed on a base material from the ink, and a color filter resist composition containing the ink.
    Type: Application
    Filed: January 16, 2013
    Publication date: December 18, 2014
    Applicant: Canon Kabushiki Kaisha
    Inventors: Takeshi Sekiguchi, Shosei Mori, Taichi Shintou, Yuko Katsumoto, Takayuki Ujifusa, Takeshi Miyazaki
  • Publication number: 20140349036
    Abstract: The present invention provides a water-insoluble coloring compound having a high solvent solubility, showing increased brightness and saturation, and being useful for increasing the green gamut and also provides an ink containing the water-insoluble coloring compound. The present invention provides a thermal transfer recording sheet including a coloring material layer formed on a base material from the ink and also provides a color filter resist composition showing an increased green gamut due to the ink.
    Type: Application
    Filed: January 16, 2013
    Publication date: November 27, 2014
    Inventors: Yuko Katsumoto, Shosei Mori, Takeshi Sekiguchi, Taichi Shintou, Takayuki Ujifusa, Takeshi Miyazaki
  • Patent number: 8696766
    Abstract: A dye of the general formula (I) where D is the residue of a diazo component; X is (C1-C6)-alkylene or oxygen-interrupted (C2-C6)-alkylene; R1 is methyl, ethyl or phenyl; R2 is hydrogen, cyano or carboxamido; R3 is phenyl or substituted phenyl; R4 is hydrogen or methyl or R3 and R4 combine with the atoms to which they are attached to form a five- or six-membered ring. The invention further relates to the process of the preparation of the dye of formula and its use.
    Type: Grant
    Filed: March 18, 2009
    Date of Patent: April 15, 2014
    Assignee: DyStar Colours Deutschland GmbH
    Inventor: Stefan Neubauer
  • Publication number: 20110306742
    Abstract: This invention relates to coloured polymer particles preferably with surface functionality for charge retention, a process for their preparation, the use of these particles for the preparation of an electrophoretic device, colour electrophoretic displays comprising such particle, and new water-soluble dyes.
    Type: Application
    Filed: January 29, 2010
    Publication date: December 15, 2011
    Applicant: MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG
    Inventors: Louise Diane Farrand, Mark James, Matthias Koch, Ashley Nathan Smith, Jonathan Henry Wilson, Mark John Goulding, Daniel Walker
  • Publication number: 20110030153
    Abstract: A dye of the general formula (I) where D is the residue of a diazo component; X is (C1-C6)-alkylene or oxygen-interrupted (C2-C6)-alkylene; R1 is methyl, ethyl or phenyl; R2 is hydrogen, cyano or carboxamido; R3 is phenyl or substituted phenyl; R4 is hydrogen or methyl or R3 and R4 combine with the atoms to which they are attached to form a five- or six-membered ring. The invention further relates to the process of the preparation of the dye of formula and its use.
    Type: Application
    Filed: March 18, 2009
    Publication date: February 10, 2011
    Applicant: DyStar Colours Deutschland GmbH
    Inventor: Stefan Neubauer
  • Patent number: 7833685
    Abstract: Provided are a coloring compound for color toner which satisfies all of solubility in an organic solvent, a color tone, and lightfastness, and does not inhibit the polymerization of a polymerizable monomer when used in a polymerized toner, and a yellow toner using the coloring compound and achieving compatibility between a good color tone and excellent lightfastness, in which, the coloring compound has a structure represented by the following formula (1).
    Type: Grant
    Filed: May 13, 2008
    Date of Patent: November 16, 2010
    Assignee: Canon Kabushiki Kaisha
    Inventors: Masatake Tanaka, Yasuaki Murai, Masayoshi Kato, Takayuki Toyoda, Takeshi Miyazaki
  • Publication number: 20100075098
    Abstract: The present invention relates to pyridinone based azo dyes and/or of anionic azo metal complex dye salts made thereof with cationic basic yellow dyes, which are characterized by an unsaturated bond in beta-position to the endocyclic N atom of the pyridinone, and to their use in optical layers for optical data recording, preferably for optical data recording using a laser with a wavelength up to 450 nm. The invention further relates to a write once read many (WORM) type optical data recording medium capable of recording and reproducing information with radiation of blue laser, which employs pyridinone based azo dyes and/or anionic azo metal complex dye salts made thereof with cationic basic yellow dyes, which are characterized by an unsaturated bond in beta-position to the endocyclic N atom of the pyridinone, in the optical layer.
    Type: Application
    Filed: May 7, 2008
    Publication date: March 25, 2010
    Inventors: Lars Luecke, Céderic Klein, Jean-Christophe Graciet, Martin Alexander Winter
  • Publication number: 20090075193
    Abstract: A coloring compound is provided which is excellent in coloring ability and transparency, has high solubility in organic solvents, and is superior in light resistance. A toner, a sheet for heat-sensitive transfer recording and an ink that use the coloring compound are also provided.
    Type: Application
    Filed: July 25, 2008
    Publication date: March 19, 2009
    Applicant: CANON KABUSHIKI KAISHA
    Inventors: Yasuaki Murai, Masashi Hirose, Masayoshi Kato, Takayuki Toyoda, Takeshi Miyazaki
  • Patent number: 7504488
    Abstract: The present invention is a dye represented by the following general formula (1), a method of producing the dye and an ink containing the dye, wherein R1 represents a hydrogen atom, an alkyl group that may be substituted, an aryl group that may be substituted or an aralkyl group that may be substituted; R2 represents an alkyl group that may be substituted, a cycloalkyl group that may be substituted or an aralkyl group that may be substituted; R3 represents an alkyl group that may be substituted, an aryl group that may be substituted or an aralkyl group that may be substituted; X1 through X3 independently represent a hydrogen atom or any substituent; and M represents a counter ion.
    Type: Grant
    Filed: May 15, 2007
    Date of Patent: March 17, 2009
    Assignee: Canon Kabushiki Kaisha
    Inventors: Takayuki Toyoda, Yasuaki Murai, Waka Hasegawa, Masashi Hirose, Kuniaki Fujimoto, Takeshi Miyazaki
  • Publication number: 20080220358
    Abstract: Provided are a coloring compound for color toner which satisfies all of solubility in an organic solvent, a color tone, and lightfastness, and does not inhibit the polymerization of a polymerizable monomer when used in a polymerized toner, and a yellow toner using the coloring compound and achieving compatibility between a good color tone and excellent lightfastness, in which, the coloring compound has a structure represented by the following formula (1).
    Type: Application
    Filed: May 13, 2008
    Publication date: September 11, 2008
    Applicant: CANON KABUSHIKI KAISHA
    Inventors: Masatake Tanaka, Yasuaki Murai, Masayoshi Kato, Takayuki Toyoda, Takeshi Miyazaki
  • Patent number: 7270702
    Abstract: The present invention discloses a yellow dye compound having a structure of the following formula (I): wherein M is H, Li, NH4 or Na. The dye compound of the present invention is particularly applied to yellow dye compound for paper-printing ink jet ink and can be made into yellow ink jet ink with greenish yellow, wide color gamut, and excellent solubility.
    Type: Grant
    Filed: June 15, 2006
    Date of Patent: September 18, 2007
    Assignee: Everlight USA, Inc.
    Inventors: Wen-Chin Lin, Tzu-Kwei Sun, Jen-Fang Lin
  • Patent number: 7193068
    Abstract: The invention provides a pyridone azo compound represented by the following Formula (I) R1, R3 and R4 each independently represent a hydrogen atom, an alkyl group having 1 to 21 carbon atoms, an alkenyl group having 2 to 21 carbon atoms, an aryl group having 6 to 21 carbon atoms, an aralkyl group having 7 to 21 carbon atoms, or a substituent having a hetero atom; at least one of R1, R3 and R4 represents a substituent having a hetero atom; R3 and R4 may be formed into a heterocycle together with a jointly bonded nitrogen atom; and R2 represents an alkyl group having 1 to 10 carbon atoms, a methoxymethyl group, or a trifluoromethyl group. The invention further provides a colorant-containing curable composition and a color filter which contain the pyridone azo compound of Formula (I) and/or a tautomer thereof as a colorant.
    Type: Grant
    Filed: July 11, 2005
    Date of Patent: March 20, 2007
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Katsumi Araki, Taeko Aizawa
  • Patent number: 7091261
    Abstract: Aqueous ink for ink-jet recording which contains at least a water-insoluble coloring matter, water and a resin as main components and which takes the form of an emulsion, in which the coloring matter is at least one yellow hue coloring matter selected from the group consisting of a quinophthalone compound represented by the formula (1); and a pyridone azo compound represented by the formula (2); The ink is ink for ink-jet recording having excellent light resistance and storage stability, and enables formation of a high quality image without blotting, and obtained recording image is excellent in water resistance as ink for ink-jet recording.
    Type: Grant
    Filed: July 26, 2000
    Date of Patent: August 15, 2006
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Yoriaki Matsuzaki, Tadashi Okuma, Ryu Oi, Osamu Kohgo
  • Patent number: 6953846
    Abstract: The present invention relates to pyrifone azo dyes of formula (1), wherein A is the radical of a diazo component of the benzene, naphthalene, diphenyl, azobenzene, thiophene, benzothiazole, benzoisothiazole, thiadiazole, indazole, benzotriazole, pyrazole, anthraquinone, naphttholic acid imide, chromone, phthalimide or diphenylene oxide series, R1 is hydrogen, unsubstituted or hydroxyl- or phenyl-substituted C1-C6alkyl, it being possible for the alkyl chain to be interrupted from C3 upwards by one or more oxygen atoms, or has the meanings of R2, R2 is a radical of formulae (2), (3), (4), (5), (6), or (7), wherein B is a bridging member, R4 is alkyl or aryl, R5 and R6 are each independently of the other alkyl, aryl or heteroaryl and A is as defined for formula (1), or R1 and R2 toghether with the nitrogen atom in NR1R2 form a heterocyclic ring, Y is cyano, —CONH2 or CH2SO3H, and n is an integer from 2 to 6, to a process for their preparation and to their use in the production coloured plastics or polymeric colo
    Type: Grant
    Filed: February 28, 2002
    Date of Patent: October 11, 2005
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Athanassios Tzikas, Urs Lauk, Romeo Dreier, Antoine Clément
  • Publication number: 20040231558
    Abstract: Aqueous ink which contains compounds having one or more structures represented by general formula (1) in a molecule or salts thereof and which has a clear hue and is excellent in light fastness and moisture resistance is provided.
    Type: Application
    Filed: March 25, 2004
    Publication date: November 25, 2004
    Inventors: Osamu Kohgo, Hiroshi Naruse, Kenichi Fujii, Tsutami Misawa, Akira Ogiso, Yasunori Saito, Rihoko Suzuki
  • Patent number: 6723835
    Abstract: Compositions containing a solvent and at least one compound of Formula (1) in which: R1 represents H, an optionally substituted C1-8carbyl derived group, or a group of Formula A: in which c is from 2 to 6; R3 represents H or optionally substituted C1-8carbyl derived group; R4 and R5 independently represent an optional substituent; R2 represents an optionally substituted C1-8carbyl derived group; X, Y and Z independently represent H or an optional substituent; M represents H or a cation; and m and n independently represent 0, 1 or 2, are useful as colorants for color filters for displays. Compounds of Formula (1) wherein at least one of R1, R2, X, Y or Z, represent SO3M or PO3M2 are also provided.
    Type: Grant
    Filed: March 20, 2002
    Date of Patent: April 20, 2004
    Assignee: Avecia Limited
    Inventors: Christine Millard, Neil Anthony Tallant
  • Publication number: 20040010058
    Abstract: Disclosed are compounds of the formula 1
    Type: Application
    Filed: June 27, 2002
    Publication date: January 15, 2004
    Applicant: Xerox Corporation
    Inventors: Rina Carlini, Jeffrey H. Banning, James M. Duff, Bo Wu, James D. Mayo
  • Publication number: 20030136301
    Abstract: A composition comprising a dye of Formula (I) and a dye of Formula (II) or salts thereof, and use of the composition in ink jet printing.
    Type: Application
    Filed: September 4, 2002
    Publication date: July 24, 2003
    Inventors: Andrew Paul Shawcross, Mark Holbrook, Paul Nicholas Ewing
  • Patent number: 6590082
    Abstract: Disclosed are compounds of the formula The compounds are useful as colorants, particularly in applications such as phase change inks.
    Type: Grant
    Filed: June 27, 2002
    Date of Patent: July 8, 2003
    Assignee: Xerox Corporation
    Inventors: Jeffrey H. Banning, Rina Carlini, James D. Mayo, James M. Duff, C. Wayne Jaeger
  • Patent number: 6582502
    Abstract: A dye which is represented by any of the following general formula (1), (2), (3) or (4), an ink for inkjet recording which contains at least one of the dyes, and an ink jet recording method which uses the ink. The dye has heterocyclic group which may be substituted and has at least one ionic aqueous group in a molecule.
    Type: Grant
    Filed: January 24, 2001
    Date of Patent: June 24, 2003
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Toshiki Fujiwara
  • Patent number: 6488752
    Abstract: Compounds of Formula (1) and salts and tautomers thereof, inks containing a compound of Formula (1), an ink jet printing process using the inks, substrates printed with the inks and ink jet printer cartridges containing the inks: wherein: R1 and R2 each independently is H, optionally substituted alkyl, optionally substituted aryl or optionally substituted arylalkyl; each W and each X independently is —COOH, —SO3H, —PO3H2 or alkyl substituted by one or more groups selected from —COOH, —SO3H and —PO3H2; each Y and each Z independently is a substituent other than those defined for W and X; a and d each independently is 1 to 5; b and c each independently is 0 to 4; (a+b) has a value of 5 or less; and (c+d) has a value of 5 or less.
    Type: Grant
    Filed: August 28, 2000
    Date of Patent: December 3, 2002
    Assignee: Avecia Limited
    Inventors: Mark Kenworthy, Ronald Wynford Kenyon
  • Patent number: 6406526
    Abstract: A dye of Formula (1) or tautomer thereof: wherein: A is di-, tri-, tetra-, or penta-substituted phenyl; R1 is methyl; R2 is H, CN, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl or a carbonamido group; and R3 is 5- or 6-membered ring comprising carbon atoms and one or two O, N and/or S atoms, wherein the ring may be substituted are useful as a component for inks, especially, ink jet printing inks and provide good storage stability, and high color strength. Inks containing the dye of formula (1) with a water dissipatable polymer in an aqueous medium produce images having high light-fastness and water-fastness and may be printed on various substrates, including paper, overhead transparencies and textiles, and may be applied using ink jet printers.
    Type: Grant
    Filed: March 9, 2000
    Date of Patent: June 18, 2002
    Assignee: Avecia Limited
    Inventors: Barry Huston Meyrick, Mark Holbrook, Roy Bradbury
  • Patent number: 6303763
    Abstract: Dyes of the Formula (1) and tautomers thereof: wherein: A is optionally substituted phenyl; R1 is H, optionally substituted alkyl, optionally substituted alkenyl or optionally substituted alkynyl; R2 is H, CN, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl or a carbonamido group; and R3 is an optionally substituted 5- or 6-membered ring; provided that R1 is not methyl. Also claimed are inks comprising a dye of the Formula (1) an aqueous medium and a water-dissipatable polymer; a method of ink jet printing using the inks; and a substrate printed with an ink according to the invention.
    Type: Grant
    Filed: December 21, 1999
    Date of Patent: October 16, 2001
    Assignee: Avecia Limited
    Inventors: Barry Huston Meyrick, Mark Holbrook, Roy Bradbury
  • Patent number: 6184363
    Abstract: The invention provides novel non-&bgr;-lactam inhibitors of &bgr;-lactamases. In particular, the invention provides such inhibitors which are boronic acids of formula (1) which is set forth in the specification. These compounds may be used with &bgr;-lactam antibiotics to treat &bgr;-lactam-antibiotic-resistant bacterial infections. These compounds are also antibacterial by themselves. Finally, the invention provides a pharmaceutical composition comprising these compounds.
    Type: Grant
    Filed: December 16, 1998
    Date of Patent: February 6, 2001
    Assignee: Northwestern University
    Inventors: Brian K. Shoichet, Grady Scott Weston
  • Patent number: 6140478
    Abstract: Basic azo compounds of formula I are suitable for coloring or printing especially of paper and leather.
    Type: Grant
    Filed: July 19, 1996
    Date of Patent: October 31, 2000
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Jurgen Geiwiz, Helmut Anton Moser, Reinhard Pedrazzi
  • Patent number: 6051360
    Abstract: Dyestuffs represented by the below-described formula (1), that is, dyestuffs formed of a chromophoric nucleus and a bisphenol introduced therein have excellent solubility in solvents and binder resins, and can provide color filters having excellent transmittance characteristics and durability. ##STR1## wherein Dye represents a chromophoric nucleus, X represents a direct bond or a divalent connecting group, R.sup.1 to R.sup.10 and n are defined with the provision that one of R.sup.9 and R.sup.10 has 3 or more carbon atoms.
    Type: Grant
    Filed: December 31, 1997
    Date of Patent: April 18, 2000
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Akio Karasawa, Hisato Itoh
  • Patent number: 6042621
    Abstract: The application is concerned with a compound of the formula (I) ##STR1## and a process for making the same. The compound is useful as fiber-reactive dyestuff in dyeing or printing onto hydroxy- or nitrogen-containing substrates. A printing composition comprising this fiber-reactive dyestuff and a copper phthalocyanine allows to obtain dyeings with less catalytic fading.
    Type: Grant
    Filed: August 11, 1998
    Date of Patent: March 28, 2000
    Assignee: Clariant Finance (BV) Limited
    Inventors: Roland Wald, Paul Doswald
  • 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: 5929218
    Abstract: The present invention relates to pyridone-based yellow monoazo dyes used in thermal transfer having following formula(I) which have good stability and hue. ##STR1## wherein, R.sub.1 is hydrogen atom; unsubstituted or substituted alkyl group of from 1 to 8 carbon atoms with alkoxy or aryl; or unsubstituted or sustituted aryl group with alkoxy or halogen.And,X is hydrogen atom; alkyl group of from 1 to 4 carbon atoms; alkoxy group; or halogen;R.sub.2 is selected from the following groups; ##STR2## wherein, R.sub.3 and R.sub.4 are independently selected from groups consisting hydrogen, substituted or unsubstituted alkyl group of from 1 to 4 carbon atoms, halogen, alkyl carboxylate, and carbonyl group;R.sub.3 -R.sub.4 is noncyclization with R.sub.3 and R.sub.4 and selected respectively from the above substituents(R.sub.3 and R.sub.
    Type: Grant
    Filed: May 8, 1996
    Date of Patent: July 27, 1999
    Assignee: Hansol Paper Co., Ltd.
    Inventors: Ki Taek Lee, Young Seup Son, Woo Sok Han, Beom Jun Joo, Soon Yeol Eom
  • Patent number: 5919914
    Abstract: Clathrates of bis?6-hydroxy-4-methyl-5-(3-methyl-imidazolium-1-yl)-3-(phen-4-ylazo)pyrid in-2-one!ethylene with aromatics of the general formula I ##STR1## where R.sup.1 is C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.5 -hydroxyalkyl, C.sub.1 -C.sub.5 -alkoxy, C.sub.1 -C.sub.5 -hydroxyalkoxy, C.sub.1 -C.sub.10 -alkyl which is interrupted by 1, 2 or 3 non-neighboring oxygen atoms and is unsubstituted or substituted by hydroxyl, C.sub.1 -C.sub.10 -alkoxy which is interrupted by 1, 2 or 3 non-neighboring oxygen atoms and is unsubstituted or substituted by hydroxyl, or is C.sub.1 -C.sub.6 -alkanoyl, hydroxy, carboxyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, phenylcarbonyl or C.sub.1 -C.sub.6 -alkenyl andR.sup.2 is R.sup.1, hydrogen or phenoxy,a process for their preparation and their use for the preparation of formulations of the dye.
    Type: Grant
    Filed: March 17, 1998
    Date of Patent: July 6, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Manfred Ruske, Peter Erk, Heidi Hengelsberg
  • Patent number: 5698681
    Abstract: Fiber-reactive disazo dyes correspond to formula I, ##STR1## and they are present as free acids or in salt form. They are used as reactive dyes for dyeing or printing hydroxy-group-containing or nitrogen-containing organic substrates, especially leather or fibrous material, which consists of or contains natural or synthetic polyamides or natural or regenerated cellulose. The dyeings obtained have high fixation values and good light fastness.
    Type: Grant
    Filed: June 19, 1996
    Date of Patent: December 16, 1997
    Assignee: Clariant Finance (BVI) Limited
    Inventor: Paul Doswald
  • Patent number: 5554737
    Abstract: Azo dyes of the formula ##STR1## where D is the radical of a diazo component, andX is substituted or unsubstituted C.sub.2 -C.sub.8 -alkylene, in the form of the free acid or its salts, the use thereof for dyeing or printing natural or synthetic substrates, sulfopyridones as coupling components for these dyes, and a process for preparing them.
    Type: Grant
    Filed: May 2, 1995
    Date of Patent: September 10, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Gunther Lamm, Helmut Reichelt, Matthias Wiesenfeldt
  • 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: 5484901
    Abstract: Isoindolineazo pigments of the general formula I ##STR1## where A is the radical of an active-methylene compound or .dbd.S;L is substituted or unsubstituted 1,4-phenylene, 1,3-phenylene or 1,5-naphthylene;K is the radical of a coupling component K--H; and the benzene ring D is optionally substituted,are useful for pigmenting high polymer organic materials.
    Type: Grant
    Filed: March 22, 1995
    Date of Patent: January 16, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Krapp, Georg Henning
  • Patent number: 5425785
    Abstract: The present invention relates to a process for dyeing polyester or polyester-containing textile materials at pH 8 to pH 11 with one or more monoazo dyestuffs of the general formula I ##STR1## in which A, R and X.sup.1 to X.sup.3 are as defined in claim 1.
    Type: Grant
    Filed: August 17, 1994
    Date of Patent: June 20, 1995
    Assignee: Hoechst Mitsubishi Kasei Co.
    Inventors: Ulrich Buhler, Ralf Zerrer
  • Patent number: 5420254
    Abstract: A compound of the formula I ##STR1## in which D is a diazo component,K is an aromatic group of formula a, b or c, ##STR2## Y is C.sub.2-3 alkylene and the remaining symbols are as defined in the specification. These compounds are useful for dyeing or printing textile substrates based on synthetic or semisynthetic, hydrophobic, high molecular weight organic materials. Preferably, the textile substrate is made from a linear aromatic polyester, cellulose 21/2 acetate or cellulose tri-acetate. The dyeings and prints obtained show good all round fastness properties such as good thermomigration properties, lightfastness, thermofixation, blistering properties as well as good wet fastness properties, especially after thermal fixation.
    Type: Grant
    Filed: October 19, 1993
    Date of Patent: May 30, 1995
    Assignee: Sandoz Ltd.
    Inventors: Ruedi Altermatt, Robert Egli, Beat Henzi
  • 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: 5352334
    Abstract: Metal-free compounds of the formula ##STR1## and 1:1 and 1:2 metal complexes thereof and acid addition salts of such metal-free compounds and 1:1 and 1:2 metal complexes,whereineach B is --A.sub.1 --NR.sub.7 R.sub.8 or --A.sub.1 --.sup..sym. NR.sub.7 R.sub.8 R.sub.9 A.sup..crclbar., the two B's being identical,whereineach A.sub.1 is linear or branched C.sub.2-8 alkylene,each R.sub.1 is hydrogen, C.sub.1-4 alkyl, C.sub.5-6 cycloalkyl, phenyl, benzyl or phenylethyl, the two R.sub.1 's being identical,each R.sub.2 is independently halo, hydroxy, nitro, carboxy, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,each T is hydrogen, cyano, --COOR.sub.4, --CON(R.sub.5).sub.2, --SO.sub.2 N(R.sub.5).sub.2,the two T's being identical, ##STR2## wherein each R.sub.3 is independently hydrogen, C.sub.1-4 alkyl, --N(R.sub.5).sub.2 or --CON(R.sub.5).sub.2,each R.sub.4 is C.sub.1-6 alkyl or phenyl(C.sub.1-3 alkyl),each R.sub.6 is C.sub.1-4 alkyl, andeach X.sub.a is --O--, --S-- or --NR.sub.5 --, andX.sub.
    Type: Grant
    Filed: November 25, 1992
    Date of Patent: October 4, 1994
    Assignee: Sandoz Ltd.
    Inventors: Helmut A. Moser, Roland Wald
  • Patent number: 5344465
    Abstract: A colorant mixture for use in printing inks contains a pigment of formula I ##STR1## a basic dye of the formula II ##STR2## where the substituents are as defined in the specification L-A. and exhibits higher color strength than that of the pigment of formula I alone.
    Type: Grant
    Filed: March 25, 1992
    Date of Patent: September 6, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Colberg, Joachim Jesse
  • Patent number: 5151506
    Abstract: Phenoneazo dyes of the formula ##STR1## where R.sup.1 is substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or substituted phenyl,R.sup.2 is cyano, carbamoyl or acetyl,R.sup.3 is substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or C.sub.3 -C.sub.12 -alkyl which is interrupted by from 1 to 3 oxygen atoms and may be substituted, andR.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl,are useful for thermal transfer processes and for dyeing or printing synthetic fabrics.
    Type: Grant
    Filed: August 16, 1990
    Date of Patent: September 29, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Volker Bach, Guenter Hansen, Gunther Lamm, Ruediger Sens
  • Patent number: 5106960
    Abstract: The present invention relates to azo dyes of the formula ##STR1## wherein X is an aryloxy radical or an unsubstituted or substituted C.sub.1 -C.sub.12 alkyl radical, a cycloalkyl radical or an aryl radical or a group of the formula ##STR2## wherein R.sub.1 is hydrogen, unsubstituted or substituted lower alkyl, cycloalkyl or aryl, and R.sub.2 is hydrogen or unsubstituted or substituted lower alkyl, or wherein R.sub.1 and R.sub.2, together with the nitrogen atom to which they are attached, form a 5- or 6-membered heterocyclic ring which may contain a further hetero-atom, Y is halogen, low molecular alkyl or low molecular alkoxy, and K is the radical of a coupling component of the benzene or naphthalene series or of the heterocyclic series.These dyes yield dyeings of good light- and wetfastness on polyamide material.
    Type: Grant
    Filed: March 22, 1991
    Date of Patent: April 21, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Rudolf Hurter, Dieter Mausezahl
  • Patent number: 5066791
    Abstract: Pyridoneazo dyes of the formula ##STR1## where L is C.sub.2 - or C.sub.3 -alkylene, R is C.sub.1 -C.sub.3 -alkyl and n is 1, 2 or 3, are useful for dyeing polyester fabrics.
    Type: Grant
    Filed: February 14, 1990
    Date of Patent: November 19, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Guenter Hansen, Gunther Lamm, Hermann Loeffler
  • Patent number: 5059683
    Abstract: Compounds of the formula ##STR1## and acid addition salts thereof whereinA.sub.1 is C.sub.1-8 alkylene; C.sub.2-8 alkylene substituted by 1 or 2 substituents selected from hydroxy, halo and cyano; C.sub.2-8 alkenylene; cyclohexylene; cyclohexylene substituted by 1 to 3 C.sub.1-4 alkyl groups; phenylene or phenylene substituted by 1 or 2 substituents selected from halo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy,B.sub.1 is ##STR2## wherein the quaternized nitrogen atom is bound to a carbon atom of A.sub.1,R is hydrogen, C.sub.1-4 alkyl, C.sub.5-6 cycloalkyl, phenyl, benzyl or phenylethyl,T is hydrogen, cyano, --COOR.sub.1, --CON(R.sub.2).sub.2, --SO.sub.2 N(R.sub.2).sub.2, ##STR3## wherein R.sub.1 is C.sub.1-6 alkyl or phenyl(C.sub.1-3 alkyl),each R.sub.3 is independently hydrogen, C.sub.1-4 alkyl, --CON(R.sub.2).sub.2 or --N(R.sub.5).sub.2, andX.sub.1 is --S--, --O-- or --N(R.sub.5)--,Y is hydrogen or a chromophoric group, andZ is ##STR4## wherein R.sub.11 is ##STR5## wherein W is --NR.sub.6 R.sub.7 or --.sup..sym.
    Type: Grant
    Filed: May 5, 1989
    Date of Patent: October 22, 1991
    Assignee: Sandoz Ltd.
    Inventors: Helmut A. Moser, Roland Wald
  • Patent number: 5055567
    Abstract: The dyes according to the invention consist of a chromophore and a radical which, on heating, forms an isocyanate or isothiocyanate group. The latter reacts with a suitable group in the environment. Dyeings of excellent thermomigration fastness are obtained. The disclosed dyes are of the formulae ##STR1## where F is the radical of an azo, anthraquinone or tricyanovinyl dye which is free of water-solubilizing groups,B and B' are each independently of the other a direct bond or a bridge member, selected from the group consisting of a straight-chain or branched alkylene group having 2 to 8 C atoms or one of the following groups ##STR2## where R is hydrogen or C.sub.1 -C.sub.6 alkyl, n is an integer from 1 to 8 and m is an integer from 2 to 4,Z is O or S,V is a group which at a temperature between 180.degree. and 240.degree. C. is eliminated as a radical HV, andV' is a direct bond which is cleaved at a temperature between 180.degree. and 240.degree. C.
    Type: Grant
    Filed: April 10, 1989
    Date of Patent: October 8, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Liechti, Karl Emmenegger, Martin Trottmann
  • Patent number: 5023324
    Abstract: Disazo and trisazo compounds free of sulfo groups which contain 6-hydroxy-4-methyl-3-N-pyridiniumpyridone-2 coupling component radicals, the preferred compounds being of the formula ##STR1## wherein R is a tetrazo component radical,each R.sub.1 is independently hydrogen, C.sub.1-4 alkyl, C.sub.2-4 hydroxyalkyl the hydroxy group of which is in other than the 1-position or --NR.sub.3 R.sub.4, wherein each of R.sub.3 and R.sub.4 is independently n-C.sub.1-4 alkyl,each R.sub.2 is independently hydrogen, n-C.sub.1-4 alkyl, n-C.sub.1-4 hydroxyalkyl or C.sub.1-4 alkoxy, andeach A.sup..crclbar. is an anion,and liquid and granulated dye compositions comprising such compounds, are useful for dyeing paper and basically dyeable substrates such as polymers and copolymers of acrylonitrile and dicyanoethylene and synthetic polyesters and polyamides modified to contain acid groups. Dyeings on paper are brilliant and possess good light fastness and good fastness to water and alcohol.
    Type: Grant
    Filed: July 29, 1986
    Date of Patent: June 11, 1991
    Assignee: Sandoz Ltd.
    Inventor: Helmut Moser
  • Patent number: 4952681
    Abstract: Compounds of the formula I ##STR1## where X is fluorine, chlorine, bromine, SO.sub.2 E or unsubstituted or substituted hydroxyl or mercapto, E is alkyl, alkenyl, cycloalkyl, aralkyl, aryl, chlorine or unsubstituted or substituted hydroxyl or amino, Y is cyano, nitro, alkanoyl, aroyl, alkylsulfonyl, arylsulfonyl, carboxyl, a carboxylic ester group or unsubstituted or substituted carbamyl, T is hydrogen, C.sub.1 -C.sub.4 -alkyl, a radical which can be introduced by electrophilic substitution or a radical of the formula --CH.dbd.B, in which B is a radical of a methylene-active compound or of an amine, and K is a radical of a coupling component, are disclosed. They are useful for dyeing synthetic fibers or plastics.
    Type: Grant
    Filed: July 27, 1988
    Date of Patent: August 28, 1990
    Assignee: Sandoz AG
    Inventors: Guenter Hansen, Ernst Schefczik, Karl-Heinz Etzbach, Helmut Reichelt, Hermann Loeffler