Having -c(=x)-, Wherein X Is Chalcogen, Attached Indirectly To Ring Carbon Of The Phthalocyanine Ring System By Nonionic Bonding (e.g., Phthalocyanine Acetic Acids, Etc.) Patents (Class 540/130)
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Patent number: 8809427Abstract: Provided is a phthalocyanine compound which is halogen-free and which has a green hue, excellent resistance to organic solvents and acids, and high chroma. Also provided are a metal-free phthalocyanine compound or a metal phthalocyanine compound represented by specified general formula (1-1) or (1-2) and having a N,N?-disubstituted imidazolone structure or piperazinedione structure introduced therein, and a coloring composition including the compound and a synthetic resin. The phthalocyanine compound of the present invention exhibits a clear green color and is halogen-free, and is thus useful as a clear green pigment for coloring materials such as a coating material, plastic, a printing ink, rubber, leather, textile printing, a color filter, a jet ink, a heat transfer ink, etc.Type: GrantFiled: August 6, 2010Date of Patent: August 19, 2014Assignee: DIC CorporationInventors: Hitoshi Kondou, Yoshiyuki Sano, Yutaka Tachikawa
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Patent number: 8795422Abstract: The present disclosure includes naphthalocyanine dyes or fused naphthalocyanine dyes represented by one of the general structures I to XV; inkjet ink formulations including the naphthalocyanine dyes; and a detection system (300) including the dyes.Type: GrantFiled: August 31, 2009Date of Patent: August 5, 2014Assignee: Hewlett-Packard Development Company, L.P.Inventors: Sivapackia Ganapathiappan, Jayprakash C. Bhatt
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Patent number: 8633310Abstract: Herein are described compounds having a structure or a pharmaceutically acceptable salt thereof, wherein Y, A, and B are as described. Methods, compositions, and medicaments related thereto are also disclosed.Type: GrantFiled: February 12, 2009Date of Patent: January 21, 2014Assignee: Allergan, Inc.Inventors: David W. Old, Danny T. Dinh
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Patent number: 8586198Abstract: A dendritic molecule represented by Formula 3: where Pc is metal phthalocyanine represented by Formula 2: where M is a core metal of the dendritic molecule; n is an integer in the range of 1 to 50; each of the Xs is a bivalent linking group independently selected from the group consisting of O, S, CH2, CO, SO2 and NHCO; and each of the Rs is independently selected from the group consisting of CN, COOH, SO3H and PO3H. The dendritic molecule containing metal phthalocyanine is dissolved in an organic solvent, and thus can be used to easily form a hole injection layer or a hole transport layer using solution deposition. The hole injection layer comprising the dendritic molecule containing metal phthalocyanine has good adhesion to an electrode and improved hole injection ability. The organic light emitting diode including the hole injection layer exhibits high luminance and emitting efficiency.Type: GrantFiled: November 28, 2007Date of Patent: November 19, 2013Assignee: Samsung Display Co., Ltd.Inventors: Tae-Woo Lee, Jong-Jin Park, Lyong-Sun Pu, Masa-Aki Kakimoto
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Patent number: 8383304Abstract: A gallium phthalocyanine compound represented by the following chemical structure I, where X represents a substituted or non-substituted alkyl group, a substituted or non-substituted alkenyl group, a substituted or non-substituted alkynyl group, a substituted or non-substituted aralkyl group, a substituted or non-substituted cycloalkyl group, a substituted or non-substituted aryl group, or a hydrogen atom, where substitution groups thereof are an alkoxy group, an alkylthio group, an alkyl group, a halogen atom, nitro group, amino group, an aryl group, carboxylic group, and cyano group, R1 to R16 independently represent a hydrogen atom, an alkoxy group, an alkylthio group, an alkyl group, a halogen atom, nitro group, or aryl group, n represents an integer of from 1 to 3 but excluding a combination in which n is 1 and X is methyl group.Type: GrantFiled: February 17, 2011Date of Patent: February 26, 2013Assignee: Ricoh Company, Ltd.Inventors: Yoshiki Yanagawa, Masafumi Ohta
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Publication number: 20120232194Abstract: Provided is a phthalocyanine compound which is halogen-free and which has a green hue, excellent resistance to organic solvents and acids, and high chroma. Also provided are a metal-free phthalocyanine compound or a metal phthalocyanine compound represented by specified general formula (1-1) or (1-2) and having a N,N?-disubstituted imidazolone structure or piperazinedione structure introduced therein, and a coloring composition including the compound and a synthetic resin. The phthalocyanine compound of the present invention exhibits a clear green color and is halogen-free, and is thus useful as a clear green pigment for coloring materials such as a coating material, plastic, a printing ink, rubber, leather, textile printing, a color filter, a jet ink, a heat transfer ink, etc.Type: ApplicationFiled: August 6, 2010Publication date: September 13, 2012Inventors: Hitoshi Kondou, Yoshiyuki Sano, Yutaka Tachikawa
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Publication number: 20110207043Abstract: A gallium phthalocyanine compound represented by the following chemical structure I, where X represents a substituted or non-substituted alkyl group, a substituted or non-substituted alkenyl group, a substituted or non-substituted alkynyl group, a substituted or non-substituted aralkyl group, a substituted or non-substituted cycloalkyl group, a substituted or non-substituted aryl group, or a hydrogen atom, where substitution groups thereof are an alkoxy group, an alkylthio group, an alkyl group, a halogen atom, nitro group, amino group, an aryl group, carboxylic group, and cyano group, R1 to R16 independently represent a hydrogen atom, an alkoxy group, an alkylthio group, an alkyl group, a halogen atom, nitro group, or aryl group, n represents an integer of from 1 to 3 but excluding a combination in which n is 1 and X is methyl group.Type: ApplicationFiled: February 17, 2011Publication date: August 25, 2011Inventors: Yoshiki YANAGAWA, Masafumi Ohta
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Publication number: 20100126377Abstract: The present invention relates to an ink composition containing a phthalocyanine coloring matter represented by the following formula (1): (wherein, each of the rings A to D independently represents a benzene ring or a pyridine ring, M represents a metal atom or the like, X represents a carbonyl group or the like, Y represents a hydrogen atom; a nitro group; a hydroxy group; a sulfo group; a carboxy group; an amino group; an alkoxy group, an alkylthio group, an alkylsulfonyl group which may be substituted; an aryloxy group, an arylthio group, an arylsulfonyl group, a heteroaryloxy group, a heteroarylthio group, a heteroarylsulfonyl group or an amino group, which may be substituted; or the like, and L is from 2 to 8) or a salt thereof; and said ink composition gives, in inkjet printing on plain paper, printed matters exhibiting an extremely excellent water fastness.Type: ApplicationFiled: July 3, 2008Publication date: May 27, 2010Applicant: Nippon Kayaku Kabushiki KaishaInventors: Takashi Yoneda, Takafumi Fujii, Shinsuke Shimizu, Hirokazu Kitayama
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Publication number: 20090047585Abstract: The present invention provides a compound represented by the following Formula (C1), or a colored curable composition containing a tetraazaporphyrin colorant having at least one group represented by the following Formula (I), and a color filter using the composition and a manufacturing method thereof: wherein Rc1: a halogen atom, aliphatic group, aryl group, heterocyclic group, cyano group, carboxyl group, carbamoyl group, aliphatic oxycarbonyl group, aryloxycarbonyl group, acyl group, hydroxyl group, aliphatic oxy group, aryloxy group, etc.Type: ApplicationFiled: July 6, 2005Publication date: February 19, 2009Applicant: FUJIFILM CorporationInventors: Nobuo Seto, Yuki Mizukawa, Toru Fujimori
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Patent number: 7459016Abstract: A method for the production of a phthalocyanine pigment preparation includes finely distributing a crude phthalocyanine pigment by dry milling, wet milling, salt kneading, acid pasting or acid swelling to give a pre-pigment, the pre-pigment is subjected to a finishing treatment in a mixture of water and an organic solvent at alkaline pH, increased temperature and in the presence of at least one pigment dispersant from the group of phthalocyanine sulphonic acids, phthalocyanine carboxylic acids, phthalocyanine sulphonate salts, phthalocyanine carboxylate salts and phthalocyanine suiphonamides.Type: GrantFiled: November 27, 2003Date of Patent: December 2, 2008Assignee: Clariant Produkte (Deutschland) GmbHInventors: Klaus Brychcy, Joachim Weber, Heidrun Mehler
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Publication number: 20080199732Abstract: A dendritic molecule represented by Formula 3: where Pc is metal phthalocyanine represented by Formula 2: where M is a core metal of the dendritic molecule; n is an integer in the range of 1 to 50; each of the Xs is a bivalent linking group independently selected from the group consisting of O, S, CH2, CO, SO2 and NHCO; and each of the Rs is independently selected from the group consisting of CN, COOH, SO3H and PO3H. The dendritic molecule containing metal phthalocyanine is dissolved in an organic solvent, and thus can be used to easily form a hole injection layer or a hole transport layer using solution deposition. The hole injection layer comprising the dendritic molecule containing metal phthalocyanine has good adhesion to an electrode and improved hole injection ability. The organic light emitting diode including the hole injection layer exhibits high luminance and emitting efficiency.Type: ApplicationFiled: November 28, 2007Publication date: August 21, 2008Inventors: Tae-Woo Lee, Jong-Jin Park, Lyong-Sun Pu, Masa-Aki Kakimoto
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Publication number: 20080154032Abstract: Disclosed is a compound of the formula wherein X1, X2, X3, and X4 each, independently of the others, are —S—, —S(?O)—, or —S(?O)2—, R1, R2, R3, and R4 each, independently of the others, are alkyl, aryl, arylalkyl, or alkylaryl, R1?, R2?, R3?, and R4? each, independently of the others, are substituents, n1, n2, n3, and n4 each, independently of the others, are 0, 1, 2, or 3, and M is an atom or group of atoms capable of bonding to the central cavity of a phthalocyanine molecule, wherein axial ligands optionally can be attached to M.Type: ApplicationFiled: December 21, 2006Publication date: June 26, 2008Inventor: Jeffrey H. Banning
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Publication number: 20080146794Abstract: Disclosed is a compound of the formula wherein M is atom or group of atoms capable of bonding to central cavity of phthalocyanine molecule, wherein axial ligands optionally can be attached to M, each R? is a substituent, each n is 0, 1, 2, 3, or 4, each R? is a substituent, each m is 0, 1, 2, or 3, each R is alkylene, arylene, arylalkylene, or alkylarylene, each X is —OH, —COOH, or wherein each Y and each Z is a direct bond, oxygen, or —NR1—, wherein R1 is hydrogen, alkyl, aryl, arylalkyl, or alkylaryl, provided that Z and Y are not both direct bonds connected to a single C?O moiety at the same time, provided that when X is —COOH, R can also be a direct bond, and each Rd is alkyl, aryl, arylalkyl, or alkylaryl.Type: ApplicationFiled: December 19, 2006Publication date: June 19, 2008Inventor: Jeffrey H. Banning
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Publication number: 20080081268Abstract: Provided is a colored curable composition, comprising at least one tetraazaporphyrin dye represented by the following Formula (C1), a color filter prepared by using the same, and a production method thereof. wherein, R1 represents a substituent group; L represents an aliphatic or aromatic connecting group; Z1 represents a non-metal atom group needed for forming a six-membered ring with carbon atoms; at least one of the multiple groups R1 has —OY, —COOY, —SO3Y, —CON(Y)CO—, —CON(Y)SO2— or —SO2N(Y)CO—; Y represents a hydrogen atom, a metal atom or a conjugate acid; and M represents two hydrogen atoms, a bivalent metal atom, a bivalent metal oxide, a bivalent metal hydroxide or a bivalent metal chloride.Type: ApplicationFiled: August 27, 2007Publication date: April 3, 2008Applicant: FUJIFILM CORPORATIONInventors: Masuji MOTOKI, Yuki MIZUKAWA, Toru FUJIMORI, Hideki TAKAKUWA
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Patent number: 7326255Abstract: The invention relates to the use, for dyeing keratin fibres, of at least one latent pigment, which is soluble in a medium that is suitable for dyeing, and which can be chemically, thermally or photochemically converted in the fibres into water-insoluble pigments, of formula A(B)x with A representing the chromophoric radical of dyes, and B representing a hydrogen atom or a group of formula (II) with Z representing a cationic water-solubilizing group Z+ or a polyethylene glycol residue, Y representing a hetero atom, F and F? representing a linear or branched C1-C14 alkylene chain, which may contain hetero atoms and may be substituted with one or more hydroxyl, amino or halogen groups. The invention also relates to processes for dyeing keratin fibres using latent pigments, to particular compositions containing them and to multi-compartment dyeing devices or “kits”.Type: GrantFiled: November 19, 2003Date of Patent: February 5, 2008Assignee: L'Oreal S.A.Inventors: Alain Lagrange, Sylvain Kravtchenko, Andrew Greaves
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Patent number: 7018456Abstract: A metal phthalocyanine compound that is useful as a black colorant suitable for use in an ink-jet recording ink, a water-based ink composition containing the metal phthalocyanine compound, and a product colored with the metal phthalocyanine compound. In particular, a metal phthalocyanine compound having, as substituents, both an acylamino group and a carboxyethylamino group on the phthalocyanine structure, or the salt thereof is used as a black colorant. Recorded images formed by the use of this colorant are excellent in light fastness and water fastness and exhibit absorption in infrared and visible regions, so that highly effective utilization can be found in printing of, for example, bar codes which are available in near-infrared ray reading.Type: GrantFiled: March 5, 2003Date of Patent: March 28, 2006Assignee: Nippon Kayaku Kabushiki KaishaInventors: Yoshinori Katoh, Isao Yamaguchi
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Patent number: 7014696Abstract: A compound of Formula (1) and salts thereof: wherein: M is 2H, Si, a metal, an oxymetal group, a hydroxymetal group or a halometal group; Pc represents a phthalocyanine nucleus of Formula (2); R1, R2 and R3 independently are H or optionally substituted C1-4 alkyl; R4 is an optionally substituted cyclic or an optionally substituted acyclic alkene optionally interrupted with a hetero atom; x and z are both greater than 0; y is 0 to 4; and the sum of (x+y+z) is 2 to 5. Also compositions and inks comprising compounds of Formula (1); processes for printing these compositions and substrates printed with said compositions and inks; and ink jet printer cartridges.Type: GrantFiled: January 23, 2003Date of Patent: March 21, 2006Assignee: Avecia LimitedInventor: Prakash Patel
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Publication number: 20040260083Abstract: A process for the production of a &bgr; type copper phthalocyanine pigment, comprising dry-milling a crude copper phthalocyanine having a purity of 97 to 100% and a primary crystal diameter of 0.5 to 100 &mgr;m at a temperature of 180 to 50° C.Type: ApplicationFiled: June 18, 2004Publication date: December 23, 2004Inventors: Osamu Shiromaru, Yusaku Ide, Toshio Oshiba, Takuya Kotani
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Publication number: 20030187250Abstract: Provided is a solubility-controallable compound being soluble in a solvent due to a solvent-philic group thereof, of which solubility in the solvent is irreversibly lowered when the group is removed by retro-Diels-Alder reaction.Type: ApplicationFiled: March 6, 2003Publication date: October 2, 2003Applicant: Canon Kabushiki KaishaInventors: Takayuki Ishikawa, Teigo Sakakibara, Daisuke Miura, Hidemitsu Uno, Noboru Ono
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Publication number: 20030180224Abstract: According to the present invention there is provided a compound for use as a photosensitiser in PDT, in photochemical internalisation in the production of a cancer vaccine or in the diagnosis or detection of medical conditions, the compound having a photosensitising chromophoric system, a sulphonamido functionality and a carboxy functionality.Type: ApplicationFiled: March 21, 2003Publication date: September 25, 2003Applicant: PHOTOPHARMICA LIMITEDInventors: Stanley Beames Brown, Andrea Lucille Bell, John Griffiths, Jack Schofield
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Publication number: 20030105321Abstract: Compound of formula 1Type: ApplicationFiled: July 12, 2002Publication date: June 5, 2003Inventors: Annemarie Wolleb, Heinz Wolleb, Gerardus De Keyzer, Barbara Wagner
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Publication number: 20020065401Abstract: The invention relates to novel soluble pigment precursors possessing not only higher thermal stability but also improved solubility characteristics and to a process for mass coloration of high temperature polymers that utilizes these novel soluble pigment precursors.Type: ApplicationFiled: November 20, 2001Publication date: May 30, 2002Inventors: Leonhard Feiler, Zhimin Hao
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Patent number: 6391505Abstract: Disclosed are a phthalocyanine crystal in which an organic acceptor compound is associated with a phthalocyanine molecule, wherein said organic acceptor compound has a reduction potential to a reference electrode (Ag+/Ag) is not less than −1.5 V and not more than −0.5 V, and an electrophotosensitive material containing said phthalocyanine crystal as an electric charge generating material, which exhibits sufficient photosensitivity even in high-speed image forming apparatuses.Type: GrantFiled: July 27, 2000Date of Patent: May 21, 2002Assignee: Kyocera Mita CorporationInventors: Kazunari Hamasaki, Yukimasa Watanabe
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Patent number: 6365720Abstract: The invention relates to a method for preparing a compound of the formula A(D)x(E)y (I) by reaction of a compound of the formula A(H)x(H)y with a pyrocarbonic acid diester of the formula wherein x and y are each independently of the other an integer from 0 to 6, but x and y are not simultaneously the number 0, A is the radical of a chromophore of the quinacridone, anthraquinone, perylene, indigo, quinophthalone, indanthrone, isoindolinone, isoindoline, dioxazine, azo, phthalocyanine or diketopyrrolopyrrole series, which radical is bonded via one or more nitrogen atoms to x groups D and via one or more oxygen atoms to y groups E, the nitrogen atoms and oxygen atoms forming part of the radical A, each group D or E independently of any other(s) is hydrogen or a group of the formula wherein at least one group D or E is not hydrogen, and L is any desired group suitable solubilization, in the presence of a base as catalyst, in which method the reaction takes place in an aromaType: GrantFiled: June 20, 2001Date of Patent: April 2, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Hans-Thomas Schacht, Ramaswami Sreenivasan, Mudaliar Dayal Chandrasekhar, Gilbert Moegle, Barbara Wagner, Charles Edward Monnier
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Patent number: 6355783Abstract: The invention relates to novel soluble pigment precursors possessing not only higher thermal stability but also improved solubility characteristics and to a process for mass coloration of high temperature polymers that utilizes these novel soluble pigment precursors. The pigment precursors of the invention are essentially of the formula A(B)x (I) where x is an integer from 1 to 8, A is the radical of a chromophore of the quinacridone, anthraquinone, perylene, indigo, quinophthalone, indanthrone, isoindolinone, isoindoline, dioxazine, azo, phthalocyanine or diketopyrrolopyrrole series, this radical being linked with xB groups via one or more heteroatoms, these heteroatoms being selected from the group consisting of N, O and S and forming part of the radical A, and B is hydrogen or a group of the formula although at least one B group is not hydrogen and when x is from 2 to 8 the B groups may be identical or different.Type: GrantFiled: September 7, 2000Date of Patent: March 12, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Leonhard Feiler, Zhimin Hao
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Patent number: 6323340Abstract: A phthalocyanine compound is provided which exhibits particularly high transmittance to a visible ray, offers a highly efficient cut of a near infrared ray, excels in the ability to effect selective absorption in a near infrared region, excels in the solubility in a solvent, excels in the compatibility with a resin, and excels in heat resistance, light resistance, and weatherability, a method for the production thereof, a near infrared absorbable dye using the same, and a heat ray shielding material, a plasma display grade filter and a near infrared absorbable material formed thereof.Type: GrantFiled: July 24, 2000Date of Patent: November 27, 2001Assignee: Nippon Shobukai Co., Ltd.Inventors: Kiyoshi Masuda, Masunori Kitao, Chie Tateyama
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Patent number: 6281339Abstract: Monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan or dioxazine dyes comprising at least one structural unit of formula (1) wherein Z is C1-C24alkoxy unsubstituted or substituted in the alkyl moiety, or uninterrupted or interrupted in the alkyl moiety by oxygen; phenoxy unsubstituted or substituted in the phenyl ring; C1-C4alkylthio unsubstituted or substituted in the alkyl moiety; phenylthio unsubstituted or substituted in the phenyl ring; amino; N-mono- or N,N-di-C1-C24-alkylamino, unsubstituted or substituted in the alkyl moiety, or uninterrupted or interrupted in the alkyl moiety by oxygen or by a radical —NR1— in which R1 is hydrogen or C1-C4alkyl; C10-C20terpeneamino; C5-C7cycloalkylamino unsubstituted or substituted in the cycloalkyl ring; phenyl- or naphthyl-amino or N—C1-C4alkyl-N-phenyl- or N—C1-C4alkyl-N-naphthyl-amino, each unsubstituted or substituted in the aryl moiety; morpholino; piperazin-1-yl or piperidin-1-yl, and X is hydType: GrantFiled: September 13, 2000Date of Patent: August 28, 2001Assignee: Ciba Specialty Chemicals CorporationInventors: Urs Lehmann, Marcel Frick
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Patent number: 6274728Abstract: Compounds of formula A(B)x (I), wherein x is an integer from 1 to 8, A is the radical of a chromophore of the quinacridone, anthraquinone, perylene, indigo, quinophthalone, indanthrone, isoindolinone, isoindoline, dioxazine, azo, phthalocyanine or diketopyrrolopyrrole series that is bonded to x groups B via one or more hetero atoms, those hetero atoms being selected from the group consisting of N, O and S and forming part of the radical A, each group B independently of any other(s) is hydrogen or a group of the formula at least one group B being a group of the formula The compounds according to the invention are used in high-molecular-weight organic materials, thermo-, photo- or chemo-sensitive recording materials, light-sensitive negative or positive resist compositions, ink compositions for ink-jet printing and color tapes for thermal transfer printing.Type: GrantFiled: December 16, 1999Date of Patent: August 14, 2001Assignee: Ciba Specialty Chemicals Corp.Inventors: Véronique Hall-Goulle, Aline Bize
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Patent number: 6222047Abstract: The invention relates to the preparation of pyrocarbonic acid diesters by an improved process and to the novel pyrocarbonic acid diesters prepared according to said process as well as to the use thereof. The core of the invention is a process for the preparation of a pyrocarbonic acid diester of formula (I) wherein R1 and R1′ are each independently of the other branched or straight-chain C1-C24alkyl, C3-C24alkenyl, C3-C24alkynyl, C4-C12cycloalkyl, C4-C12cycloalkenyl or C7-C24aralkyl, each of which is unsubstituted or substituted by one or more than one substituent which is inert under the reaction conditions, by reacting at least one ester carbonate of formula (II) with 40-50 mol % of a sulfochloride of formula (IV) in the presence of 0.Type: GrantFiled: January 13, 1998Date of Patent: April 24, 2001Assignee: Ciba Specialty Chemicals CorporationInventors: John Zambounis, Véronique Hall-Goulle
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Patent number: 6149722Abstract: Phthalocyanine compounds of Formula (1) have utility as colorants in inks for ink-jet printing, where Formula (1) represents: ##STR1## in which: M represents a metal or H;Pc represents a phthalocyanine nucleus; andR.sup.1 represents H or --(CH.sub.2).sub.n R.sup.3 ; R.sup.2 represents(CH.sub.2).sub.n R.sup.3 ; or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached represent a 5 or 6-membered ring; where:n is independently an integer from 1 to 30; andR.sup.3 is independently a group selected from hydroxy, sulpho, cyano, --SR.sup.4, --CO.sub.2 R.sup.5, --PO.sub.3 H.sub.2 and --NR.sup.6 R.sup.7 ; where:R.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently represent H, C.sub.1-30 alkyl optionally substituted by one or more groups selected from hydroxy, mercapto, sulpho, carboxy, cyano and --PO.sub.3 H.sub.2 ;v is the valence of Pc divided by the valence of M;x is from 1.2 to 3.8;y is from 0.1 to 2.7;z is from 0.1 to 2.7; andx, y and z satisfy 2.ltoreq.x+y+z.ltoreq.4.Type: GrantFiled: February 1, 1999Date of Patent: November 21, 2000Assignee: Zeneca LimitedInventors: Colin Dick Robertson, Mark Kenworthy
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Patent number: 6124451Abstract: A process for the preparation of substituted amido phthalocyanines having the general formula I:MPc--(CONR.sup.1 R.sup.2).sub.n Ivia the reaction of a phthalocyanine carboxamide having the formula MPc(CONH.sub.2).sub.x wherein Pc is a Phthalocyanine ring; M is a hydrogen or a metal capable of forming a metal phthalocyanine such as Mg, Al, Ni, Fe, Zn, Pb, Sn or Cu and x is a number from 0.1 to 4.0, with an amine acid salt denoted by formula II: ##STR1## wherein R.sup.1 and R.sup.2 are independently selected from the group consisting of hydrogen; an alkyl group having 1-20 carbons; a cyclic alkyl group; an aryl group; an arylalkyl having 1-20 carbons; an alcohol group having 2-20 carbons; an alkyl amino alkyl group; an aliphatic amine having 1-20 carbons; an aliphatic amine acid salt having 1-20 carbons; polyoxyalkylene groups ranging in molecular weight 89-2000; polyoxyalkyleneamines ranging in molecular weight 148-4000; Z is the hydrogen sulphate or the hydrochloride salt of the amine.Type: GrantFiled: August 17, 1999Date of Patent: September 26, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Thomas Healy, Cairan Thomas Ewins
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Patent number: 6090786Abstract: The present invention relates to new compounds of the general formula: Z-Xaa-Y', in which Xaa is an amino acid, Z is a protecting group and Y' is one of various types of ring structures. The new compounds have a modulating activity on serine proteases. The invention further relates to the use of the compounds in therapy and diagnosis and to a method of purifying the serine protease DPPIV.Type: GrantFiled: February 19, 1997Date of Patent: July 18, 2000Assignee: FondaTech Benelux N.V.Inventors: Koen Jan Ludovicus Augustyns, Greta Constantia Vanhoof, Marianne Jean Frieda Borloo, Ingrid Anna Jozef De Meester, Filip Jozef Anny Goossens, Achiel Jean-Marie Haemers, Dirk Frans Hendriks, Anne-Marie Virginie Renee Lambeir, Simon Lodewijk Scharpe
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Patent number: 5817770Abstract: The ethyl ester of derivatives of benzoyl ecgonine are provided having a linking group at the para position of the benzoyl group. The derivatives are used to bond to immunogenic polypeptides for production of antisera and monoclonal antibodies. The antisera and antibodies find use in assays, for treatment of cocaine overdose and detoxification.Type: GrantFiled: March 21, 1997Date of Patent: October 6, 1998Assignee: Drug Abuse Sciences, Inc.Inventors: Jean-Michel Scherrmann, Philippe Pouletty, Herve Galons
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Patent number: 5789137Abstract: Dyes suitable for use in the fabrication of color filters are described which contain one or more photopolymerizable substituents preferably represented by the following formula:D--(A--Yn.sup.1)n.sup.2 (1)where D represents a chromphoric nucleus, A denotes a connecting group, Y means the photopolymerizable group, .sub.n.sup.1 is 1-10,000, and .sub.n.sup.2 stands for an integer of 1-10. Also described are photosensitive resist resin compositions containing the dyes as well as color filters fabricated by curing the photosensitive resist resin compositions.Type: GrantFiled: May 24, 1996Date of Patent: August 4, 1998Assignee: Mitsui Chemicals, Inc.Inventors: Hisato Itoh, Akio Karasawa, Kenichi Sugimoto
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Patent number: 5618930Abstract: A novel phthalocyanine compound having improved solubility and high purity and containing a polymerizable vinyl group within its molecule is provided. Intermediates to this phthalocyanine compound also have improved solubility and high purity. Further, with the novel phthalocyanine compound used as a starting monomer, a novel polymer is obtained which has a high content of (metal) phthalocyanine and is easy to control the orientation of phthalocyanine rings. The polymer having improved solubility and high purity is expected of use as functional material such as catalysts and recording material.Type: GrantFiled: March 1, 1996Date of Patent: April 8, 1997Assignees: Hirofusa Shirai, TDK CorporationInventors: Mutsumi Kimura, Hirofusa Shirai, Toshiki Koyama, Kenji Hanabusa, Yuichi Kubota
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Patent number: 5618929Abstract: Substituted phthalocyanines of a formula (I) ##STR1## wherein M is a metal atom or a metal halide or oxide, or M is 2H, one H being bonded to each of the bonding N atoms (29 and 31 positions) shown, R.sub.1 to R.sub.8 are the same or different and are independently selected from C.sub.1 to C.sub.20 alkyl, C.sub.1 -C.sub.20 alkenyl, --X--COO--X.sup.1, --X--O--Y, .alpha., and --X--COZ where X is independently selected from a chemical bond, (--CH.sub.2).sub.n where n=0-20 or (CH.sub.2).sub.n --CH.dbd.CH (--CH.sub.2).sub.b where a and b are independently selected from 0-20 and a+b is in the range 0-20, X.sup.1 is independently selected from C.sub.1 -C.sub.20 alkyl or C.sub.2 -C.sub.20 alkenyl, Y is independently selected from C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.20 alkenyl or H and Z is selected from OH or NR.sup.1 R.sup.11 where R.sup.1 and R.sup.11 are independently selected from H, C.sub.1 -C.sub.20 alkyl and C.sub.2 -C.sub.Type: GrantFiled: June 7, 1995Date of Patent: April 8, 1997Assignee: The Secretary of State for Defence in Her Brittanic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Kenneth J. Harrison, Michael J. Cook, Andrew J. Thomson, Neil B. McKeown, Mervyn F. Daniel, Adrian J. Dunn
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Patent number: 5516900Abstract: A novel phthalocyanine compound having improved solubility and high purity and containing a polymerizable vinyl group within its molecule is provided. Intermediates to this phthalocyanine compound also have improved solubility and high purity. Further, with the novel phthalocyanine compound used as a starting monomer, a novel polymer is obtained which has a high content of (metal) phthalocyanine and is easy to control the orientation of phthalocyanine rings. The polymer having improved solubility and high purity is expected of use as functional material such as catalysts and recording material.Type: GrantFiled: September 14, 1994Date of Patent: May 14, 1996Assignees: Hirofusa Shirai, TDK CorporationInventors: Mutsumi Kimura, Hirofusa Shirai, Toshiki Koyama, Kenji Hanabusa, Yuichi Kubota
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Patent number: 5359056Abstract: A novel fluorine-containing phthalocyanine compound represented by the following formula (I): ##STR1## wherein Y is ##STR2## wherein R.sub.1 and R.sub.2 are independently a hydrogen atom or a C1-C8 alkyl group; R.sub.3 and R.sub.4 are independently a C1-C8 alkyl group; X is a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkoxyl group or a halogen atom; Z is a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkoxyl group, a C1-C4 alkoxycarbonyl group or a halogen atom; W is a C1-C4 alkoxyl group; e, f, g, h and j are independently an integer of 1 or 2; n is an integer of 1 to 8; and p and q are independently an integer of 1 to 6; a to d are an integer of 0 to 2 with the proviso that the sum of a to d is 1 to 8; and M is a non-metal, a metal, a metal oxide, a metal carbonyl or a metal halide, and further, a method of producing a fluorine-containing phthalocyanine compound represented by the above formula (I).Type: GrantFiled: July 14, 1992Date of Patent: October 25, 1994Assignee: Nippon Shokubai Co., Ltd.Inventors: Osamu Kaieda, Takashi Yodoshi, Hideki Itoh, Miho Onozaki
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Patent number: 5296023Abstract: A colorant of Formula (1): ##STR1## wherein: L is a metal cation or hydrogen;Pc is a phthalocyanine radical having a valency from 3 to 4;R.sup.1 is H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, aralkyl or substituted aralkyl;R.sup.2 is H, alkyl, alkoxy, halo or an optionally substituted amino group;M.sup.+ is NH.sub.4.sup.+ or a substituted annonium cation; and(t+q) is from 3 to 4 inclusive;with the proviso that the group CO.sub.2 -M.sup.+ is at the 2-, 3-, 5- or 6-position in Formula (1).Type: GrantFiled: January 4, 1993Date of Patent: March 22, 1994Assignee: Zeneca LimitedInventors: Peter Gregory, Ronald W. Kenyon
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Patent number: 5250111Abstract: A pigment composition comprising a) a pigment; and b) a phthalocyanine compound having the formula I:MPc(CH.sub.2 NHCO--A).sub.n Iin which Pc represents a phthalocyanine residue which is optionally further substituted by up to an average of one chlorine or bromine atom or by a sulphonic acid group; M is hydrogen or a metal capable of forming a metal phthalocyanine; n is a number ranging from 0.1 to 4.0; and A is C.sub.3 -C.sub.21 alkenyl, C.sub.5 -C.sub.8 cycloalkyl, C.sub.7 -C.sub.11 aralkyl, C.sub.6 -C.sub.10 aryl, a 5- or 6-membered heterocyclic residue or a fused heterocyclic system.Type: GrantFiled: April 6, 1992Date of Patent: October 5, 1993Assignee: Ciba-Geigy CorporationInventors: Robert Langley, Michael D. McFarland
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Patent number: 5229507Abstract: Compounds of the formula I ##STR1## in which R is the group --OC.sub.m H.sub.2mn R.sub.1 and M is two H or is Cu or Ni, R.sub.1 is --OH, --Cl, --Br, C.sub.1 -C.sub.30 alkoxy or --OC(O)R.sub.2, m is an integer from 2 to 6 and n is a number from 1 to 20, and R.sub.2 is C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.20 alkenyl, cyclopentyl, cyclohexyl or C.sub.6 -C.sub.10 aryl or C.sub.6 -C.sub.10 arylmethyl which is unsubstituted or substituted by C.sub.1 -C.sub.18 alkyl.The compounds are dyes and IR absorbers and can be used for optical information storage systems employing diode lasers.Type: GrantFiled: November 16, 1990Date of Patent: July 20, 1993Assignee: Ciba-Geigy CorporationInventors: Marcus Baumann, Hanspeter Stricker, Walter Fischer, Jurgen Vogt, Jin Mizuguchi
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Patent number: 5189154Abstract: Anionic phthalocyanine compounds which, in the free acid form, have the Formula (1):Pc(SO.sub.3 H).sub.t (SO.sub.2 --NR.sup.1 --L--NR.sup.2 --X--NR.sup.3 --G).sub.q (1)The compounds are useful as the colored component of inks, particularly those used in ink jet printing.Type: GrantFiled: June 28, 1991Date of Patent: February 23, 1993Assignee: Imperial Chemical Industries PLCInventors: Peter Gregory, Ronald W. Kenyon, Christine Millard
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Patent number: 5166338Abstract: Anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone and perylenetetracarbimide dyes which contain one or two groups of the general formula ##STR1## where Y is vinyl or an ethyl group which contains in a .beta.-position a substituent which is eliminable by means of alkali to form a vinyl group, and W is a direct bond or a group of the general formula ##STR2## where M is a hydrogen atom or an alkali metal and n is zero, 1 or 2. The dyes have very good fiber-reactive properties and are advantageously suitable for dyeing carboxamino- and/or hydroxy-containing material, for example wool, in particular cellulose fiber materials; on these materials they produce strong fast shades in a high degree of fixation.Type: GrantFiled: February 13, 1991Date of Patent: November 24, 1992Assignee: Hoechst AktiengesellschaftInventors: Holger M. Buch, Josef Geisenberger, Hartmut Springer
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Patent number: 5023325Abstract: A reactive dye of the formulaD--U--R).sub.nin which D is the radical of an anthraquinone, phthalocyanine, formazane, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye; U is --CO-- or --SO.sub.2 --; R is a radical of the formula ##STR1## Z is sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-acetoxyethyl, .beta.-halogenoethyl or vinyl; alk is a polymethylene radical having 1 to 6 C atoms or its branched isomers; Y is hydrogen, chlorine, bromine, fluorine, hydroxyl, sulfato, C.sub.1 -C.sub.4 -alkanoyloxy, cyano, carboxyl, alkoxycarbonyl having 1 to 5 C atoms, carbamoyl or a radical --SO.sub.2 --Z in which Z is as defined above; V is hydrogen or C.sub.1 -C.sub.4 -alkyl which is unsubstituted or substituted by carboxyl, sulfo, C.sub.1 -C.sub.2 -alkoxy, halogen or hydroxyl;or a radical ##STR2## in which Z, alk and Y are as defined above; R.sub.1 is hydrogen or C.sub.1 -C.sub.Type: GrantFiled: May 11, 1988Date of Patent: June 11, 1991Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Peter Aeschlimann
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Patent number: 4978747Abstract: Colorants are obtained by reacting a dyestuff which is free from ionic groups and has.gtoreq.2 NH.sub.2 groups which are preferably arranged in such a manner that they do not participate in the resonance of the chromophore with such an amount of a (cyclo)aliphatic diisocyante so as to form an adduct that still contains at least two free NCO groups, and subsequently reacting this adduct with a (cyclo)aliphatic diamine, to form an adduct suitable for dyeing and pigmenting macromolecular substances, in particular for coloring PUR-based paints, coatings and laminates.Type: GrantFiled: April 13, 1989Date of Patent: December 18, 1990Assignee: Bayer AktiengesellschaftInventors: Karl-Arnold Weber, Hermann Henk, Klaus Kunde, Jochen Westphal, Klaus Wunderlich
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Patent number: 4968782Abstract: Reactive dyes of the formula ##STR1## in which D is the radial of an anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye; Q is hydrogen or alkyl which has 1 to 4 carbon atoms and can be substituted by carboxyl, sulfo, cyano, hydroxyl, C.sub.1- C.sub.4 alkoxy or halogen; B is a radical --CH.sub.2n, --O--CH.sub.2n or --NH --CH.sub.2n and n is 1 to 6; R is a radical of the formula ##STR2## Z is .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-acyloxyethyl, .beta.-halogenoethyl or vinyl; alk is an alkylene radical having 1 to 6 C atoms or branched isomers thereof; Y is hydrogen, chlorine, bromine, flourine, hydroxyl, sulfato, acyloxy having 1 to 4 C atoms, cyano, carboxyl, alkoxycarbonyl having 1 to 5 C atoms, carbamoyl or a radical --SO.sub.Type: GrantFiled: October 13, 1989Date of Patent: November 6, 1990Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Peter Aeschlimann
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Patent number: 4960538Abstract: Disclosed are near-infrared absorbents comprising 1,2-naphthalocyanine derivatives wherein the four naphthalene rings contained in the molecule independently have 1 to 6 substituents. Also disclosed is the use of these near-infrared absorbents in optical recording media, near-infrared absorption filters and display materials.Type: GrantFiled: October 20, 1988Date of Patent: October 2, 1990Assignees: Mitsui Toatsu Chemicals, Inc, Yamamoto Chemicals, Inc.Inventors: Hisato Itoh, Takahisa Oguchi, Katashi Enomoto, Masakatsu Nakatsuka, Tsutomu Nishizawa
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Patent number: 4885360Abstract: Reactive dyes of the formula ##STR1## in which D is the radical of a dye of the monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide series, R.sub.1 and R.sub.2, independently of each other, are each hydrogen or the radical of an unsubstituted or substituted hydrocarbon, A is an unsubstituted or substituted aliphatic or aromatic bridge member, n is 0 or 1, Y is a --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --X radical, X is an inorganic or organic radical detachable under alkaline conditions, Z is a radical of the formula ##STR2## and Hal is chlorine or bromine, and if n is 1 Z must not be either of the two radicals mentioned at the end for Z, are suitable for dyeing or printing cellulose fibre materials and produce lightfast and wetfast dyeings or prints.Type: GrantFiled: November 21, 1988Date of Patent: December 5, 1989Assignee: Ciba-Geigy CorporationInventor: Peter Scheibli
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Patent number: 4841028Abstract: Reactive dyes of the formula ##STR1## in which D is the radical of an organic dye of the monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide series, R is hydrogen or substituted or unsubstituted C.sub.1-4 -alkyl, A is a polymethylene radical having 2 to 6 C atoms (or its branched isomers) which can be substituted by chlorine, bromine, fluorine, hydroxyl, sulfato, acyloxy having 1 to 4 C atoms, cyano, carboxyl, alkoxycarbonyl having 1 to 5 C atoms or carbamoyl, or an alkyleneoxalkylene radical having 1 to 6 C atoms in each alkylene member, independently of each other; Y is a radical --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.Type: GrantFiled: August 10, 1987Date of Patent: June 20, 1989Inventors: Peter Aeschlimann, Hansrudolf Schwander
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Patent number: RE35145Abstract: A phthalocyanine compound of the formula:(R--X--).sub.m Pc(--Y--R.sup.1 --Z--).sub.n (--SO.sub.3 M).sub.p IwhereinPc is a phthalocyanine nucleus (Pc);eachR independently is a monovalent aromatic radical linked to a peripheral carbon atom of the Pc nucleus through X;X selected from S, Se and Te;m is 4 to 16;eachR.sup.1 independently is a divalent aromatic radical linked to two adjacent peripheral carbon atoms of the Pc nucleus through Y and Z;Y is selected from S, NT, Se and Te;Z is selected from S, Se, Te, NT and O;T is selected from H, alkyl and aryl;n is 0 to 7;M is H, a metal or optionally-substituted ammonium;andP is from 1 to 16.The compounds have a significant absorption band in the near infra red and depending on the number of sulphonic acids groups and the nature of the counter ion are soluble in aqueous and polar organic media.Type: GrantFiled: October 25, 1993Date of Patent: January 9, 1996Assignee: Zeneca LimitedInventors: William Stark, Nigel Hughes, Donald M. Gunn