Plural Acyclic Chalcogens Bonded Directly To The Hetero Ring At The Two Positions Adjacent To The Ring Nitrogen Patents (Class 534/772)
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Patent number: 9910196Abstract: 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: GrantFiled: September 24, 2014Date of Patent: March 6, 2018Assignee: Canon Kabushiki KaishaInventors: Takeshi Sekiguchi, Shosei Mori, Taichi Shintou, Takeshi Miyazaki
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Patent number: 9388313Abstract: 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: GrantFiled: January 16, 2013Date of Patent: July 12, 2016Assignee: Canon Kabushiki KaishaInventors: Yuko Katsumoto, Shosei Mori, Takeshi Sekiguchi, Taichi Shintou, Takayuki Ujifusa, Takeshi Miyazaki
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Patent number: 9382426Abstract: 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: GrantFiled: January 16, 2013Date of Patent: July 5, 2016Assignee: Canon Kabushiki KaishaInventors: Takeshi Sekiguchi, Shosei Mori, Taichi Shintou, Yuko Katsumoto, Takayuki Ujifusa, Takeshi Miyazaki
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Publication number: 20150073132Abstract: 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: ApplicationFiled: November 30, 2012Publication date: March 12, 2015Inventors: Shufen Zhang, Bingtao Tang, Rongwen Lv, Dong Liang
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Publication number: 20140370207Abstract: 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: ApplicationFiled: January 16, 2013Publication date: December 18, 2014Applicant: Canon Kabushiki KaishaInventors: Takeshi Sekiguchi, Shosei Mori, Taichi Shintou, Yuko Katsumoto, Takayuki Ujifusa, Takeshi Miyazaki
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Publication number: 20140349036Abstract: 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: ApplicationFiled: January 16, 2013Publication date: November 27, 2014Inventors: Yuko Katsumoto, Shosei Mori, Takeshi Sekiguchi, Taichi Shintou, Takayuki Ujifusa, Takeshi Miyazaki
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Patent number: 8696766Abstract: 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: GrantFiled: March 18, 2009Date of Patent: April 15, 2014Assignee: DyStar Colours Deutschland GmbHInventor: Stefan Neubauer
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Publication number: 20110306742Abstract: 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: ApplicationFiled: January 29, 2010Publication date: December 15, 2011Applicant: MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNGInventors: Louise Diane Farrand, Mark James, Matthias Koch, Ashley Nathan Smith, Jonathan Henry Wilson, Mark John Goulding, Daniel Walker
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Publication number: 20110030153Abstract: 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: ApplicationFiled: March 18, 2009Publication date: February 10, 2011Applicant: DyStar Colours Deutschland GmbHInventor: Stefan Neubauer
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Patent number: 7833685Abstract: 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: GrantFiled: May 13, 2008Date of Patent: November 16, 2010Assignee: Canon Kabushiki KaishaInventors: Masatake Tanaka, Yasuaki Murai, Masayoshi Kato, Takayuki Toyoda, Takeshi Miyazaki
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Publication number: 20100075098Abstract: 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: ApplicationFiled: May 7, 2008Publication date: March 25, 2010Inventors: Lars Luecke, Céderic Klein, Jean-Christophe Graciet, Martin Alexander Winter
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Publication number: 20090075193Abstract: 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: ApplicationFiled: July 25, 2008Publication date: March 19, 2009Applicant: CANON KABUSHIKI KAISHAInventors: Yasuaki Murai, Masashi Hirose, Masayoshi Kato, Takayuki Toyoda, Takeshi Miyazaki
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Patent number: 7504488Abstract: 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: GrantFiled: May 15, 2007Date of Patent: March 17, 2009Assignee: Canon Kabushiki KaishaInventors: Takayuki Toyoda, Yasuaki Murai, Waka Hasegawa, Masashi Hirose, Kuniaki Fujimoto, Takeshi Miyazaki
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Publication number: 20080220358Abstract: 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: ApplicationFiled: May 13, 2008Publication date: September 11, 2008Applicant: CANON KABUSHIKI KAISHAInventors: Masatake Tanaka, Yasuaki Murai, Masayoshi Kato, Takayuki Toyoda, Takeshi Miyazaki
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Patent number: 7270702Abstract: 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: GrantFiled: June 15, 2006Date of Patent: September 18, 2007Assignee: Everlight USA, Inc.Inventors: Wen-Chin Lin, Tzu-Kwei Sun, Jen-Fang Lin
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Patent number: 7193068Abstract: 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: GrantFiled: July 11, 2005Date of Patent: March 20, 2007Assignee: Fuji Photo Film Co., Ltd.Inventors: Katsumi Araki, Taeko Aizawa
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Patent number: 7091261Abstract: 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: GrantFiled: July 26, 2000Date of Patent: August 15, 2006Assignee: Mitsui Chemicals, Inc.Inventors: Yoriaki Matsuzaki, Tadashi Okuma, Ryu Oi, Osamu Kohgo
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Patent number: 6953846Abstract: 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 coloType: GrantFiled: February 28, 2002Date of Patent: October 11, 2005Assignee: Ciba Specialty Chemicals CorporationInventors: Athanassios Tzikas, Urs Lauk, Romeo Dreier, Antoine Clément
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Publication number: 20040231558Abstract: 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: ApplicationFiled: March 25, 2004Publication date: November 25, 2004Inventors: Osamu Kohgo, Hiroshi Naruse, Kenichi Fujii, Tsutami Misawa, Akira Ogiso, Yasunori Saito, Rihoko Suzuki
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Patent number: 6723835Abstract: 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: GrantFiled: March 20, 2002Date of Patent: April 20, 2004Assignee: Avecia LimitedInventors: Christine Millard, Neil Anthony Tallant
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Publication number: 20040010058Abstract: Disclosed are compounds of the formula 1Type: ApplicationFiled: June 27, 2002Publication date: January 15, 2004Applicant: Xerox CorporationInventors: Rina Carlini, Jeffrey H. Banning, James M. Duff, Bo Wu, James D. Mayo
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Publication number: 20030136301Abstract: 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: ApplicationFiled: September 4, 2002Publication date: July 24, 2003Inventors: Andrew Paul Shawcross, Mark Holbrook, Paul Nicholas Ewing
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Patent number: 6590082Abstract: Disclosed are compounds of the formula The compounds are useful as colorants, particularly in applications such as phase change inks.Type: GrantFiled: June 27, 2002Date of Patent: July 8, 2003Assignee: Xerox CorporationInventors: Jeffrey H. Banning, Rina Carlini, James D. Mayo, James M. Duff, C. Wayne Jaeger
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Patent number: 6582502Abstract: 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: GrantFiled: January 24, 2001Date of Patent: June 24, 2003Assignee: Fuji Photo Film Co., Ltd.Inventor: Toshiki Fujiwara
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Patent number: 6488752Abstract: 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: GrantFiled: August 28, 2000Date of Patent: December 3, 2002Assignee: Avecia LimitedInventors: Mark Kenworthy, Ronald Wynford Kenyon
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Patent number: 6406526Abstract: 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: GrantFiled: March 9, 2000Date of Patent: June 18, 2002Assignee: Avecia LimitedInventors: Barry Huston Meyrick, Mark Holbrook, Roy Bradbury
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Patent number: 6303763Abstract: 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: GrantFiled: December 21, 1999Date of Patent: October 16, 2001Assignee: Avecia LimitedInventors: Barry Huston Meyrick, Mark Holbrook, Roy Bradbury
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Patent number: 6184363Abstract: 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: GrantFiled: December 16, 1998Date of Patent: February 6, 2001Assignee: Northwestern UniversityInventors: Brian K. Shoichet, Grady Scott Weston
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Patent number: 6140478Abstract: Basic azo compounds of formula I are suitable for coloring or printing especially of paper and leather.Type: GrantFiled: July 19, 1996Date of Patent: October 31, 2000Assignee: Clariant Finance (BVI) LimitedInventors: Jurgen Geiwiz, Helmut Anton Moser, Reinhard Pedrazzi
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Patent number: 6051360Abstract: 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: GrantFiled: December 31, 1997Date of Patent: April 18, 2000Assignee: Mitsui Chemicals, Inc.Inventors: Akio Karasawa, Hisato Itoh
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Patent number: 6042621Abstract: 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: GrantFiled: August 11, 1998Date of Patent: March 28, 2000Assignee: Clariant Finance (BV) LimitedInventors: Roland Wald, Paul Doswald
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Patent number: 5986075Abstract: 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: GrantFiled: January 20, 1999Date of Patent: November 16, 1999Assignees: Bayer Corporation, Bayer AktiengesellschaftInventors: John C. DuBose, Andrew D. Johnson, Samuel Shaun Murphree, Edzard Tholema, Helmut Hoffmann, Wolfgang Zarges, Wolfgang Frank, Bettina Burkhardt
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Patent number: 5929218Abstract: 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: GrantFiled: May 8, 1996Date of Patent: July 27, 1999Assignee: Hansol Paper Co., Ltd.Inventors: Ki Taek Lee, Young Seup Son, Woo Sok Han, Beom Jun Joo, Soon Yeol Eom
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Patent number: 5919914Abstract: 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: GrantFiled: March 17, 1998Date of Patent: July 6, 1999Assignee: BASF AktiengesellschaftInventors: Manfred Ruske, Peter Erk, Heidi Hengelsberg
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Patent number: 5698681Abstract: 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: GrantFiled: June 19, 1996Date of Patent: December 16, 1997Assignee: Clariant Finance (BVI) LimitedInventor: Paul Doswald
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Patent number: 5554737Abstract: 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: GrantFiled: May 2, 1995Date of Patent: September 10, 1996Assignee: BASF AktiengesellschaftInventors: Gunther Lamm, Helmut Reichelt, Matthias Wiesenfeldt
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Patent number: 5510468Abstract: 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: GrantFiled: July 27, 1994Date of Patent: April 23, 1996Assignee: BASF AktiengesellschaftInventors: Gunther Lamm, Helmut Reichelt, Ortwin Schaffer
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Patent number: 5484901Abstract: 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: GrantFiled: March 22, 1995Date of Patent: January 16, 1996Assignee: BASF AktiengesellschaftInventors: Michael Krapp, Georg Henning
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Patent number: 5425785Abstract: 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: GrantFiled: August 17, 1994Date of Patent: June 20, 1995Assignee: Hoechst Mitsubishi Kasei Co.Inventors: Ulrich Buhler, Ralf Zerrer
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Patent number: 5420254Abstract: 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: GrantFiled: October 19, 1993Date of Patent: May 30, 1995Assignee: Sandoz Ltd.Inventors: Ruedi Altermatt, Robert Egli, Beat Henzi
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Patent number: 5380859Abstract: 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: GrantFiled: July 16, 1993Date of Patent: January 10, 1995Assignee: Basf AktiengesellschaftInventors: Gunther Lamm, Helmut Beichelt, Ortwin Schaffer
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Patent number: 5352334Abstract: 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: GrantFiled: November 25, 1992Date of Patent: October 4, 1994Assignee: Sandoz Ltd.Inventors: Helmut A. Moser, Roland Wald
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Patent number: 5344465Abstract: 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: GrantFiled: March 25, 1992Date of Patent: September 6, 1994Assignee: BASF AktiengesellschaftInventors: Horst Colberg, Joachim Jesse
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Patent number: 5151506Abstract: 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: GrantFiled: August 16, 1990Date of Patent: September 29, 1992Assignee: BASF AktiengesellschaftInventors: Volker Bach, Guenter Hansen, Gunther Lamm, Ruediger Sens
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Patent number: 5106960Abstract: 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: GrantFiled: March 22, 1991Date of Patent: April 21, 1992Assignee: Ciba-Geigy CorporationInventors: Rudolf Hurter, Dieter Mausezahl
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Patent number: 5066791Abstract: 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: GrantFiled: February 14, 1990Date of Patent: November 19, 1991Assignee: BASF AktiengesellschaftInventors: Guenter Hansen, Gunther Lamm, Hermann Loeffler
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Patent number: 5059683Abstract: 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: GrantFiled: May 5, 1989Date of Patent: October 22, 1991Assignee: Sandoz Ltd.Inventors: Helmut A. Moser, Roland Wald
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Patent number: 5055567Abstract: 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: GrantFiled: April 10, 1989Date of Patent: October 8, 1991Assignee: Ciba-Geigy CorporationInventors: Peter Liechti, Karl Emmenegger, Martin Trottmann
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Patent number: 5023324Abstract: 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: GrantFiled: July 29, 1986Date of Patent: June 11, 1991Assignee: Sandoz Ltd.Inventor: Helmut Moser
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Patent number: 4952681Abstract: 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: GrantFiled: July 27, 1988Date of Patent: August 28, 1990Assignee: Sandoz AGInventors: Guenter Hansen, Ernst Schefczik, Karl-Heinz Etzbach, Helmut Reichelt, Hermann Loeffler