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)
  • Patent number: 8809427
    Abstract: 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: Grant
    Filed: August 6, 2010
    Date of Patent: August 19, 2014
    Assignee: DIC Corporation
    Inventors: Hitoshi Kondou, Yoshiyuki Sano, Yutaka Tachikawa
  • Patent number: 8795422
    Abstract: 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: Grant
    Filed: August 31, 2009
    Date of Patent: August 5, 2014
    Assignee: Hewlett-Packard Development Company, L.P.
    Inventors: Sivapackia Ganapathiappan, Jayprakash C. Bhatt
  • Patent number: 8633310
    Abstract: 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: Grant
    Filed: February 12, 2009
    Date of Patent: January 21, 2014
    Assignee: Allergan, Inc.
    Inventors: David W. Old, Danny T. Dinh
  • Patent number: 8586198
    Abstract: 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: Grant
    Filed: November 28, 2007
    Date of Patent: November 19, 2013
    Assignee: Samsung Display Co., Ltd.
    Inventors: Tae-Woo Lee, Jong-Jin Park, Lyong-Sun Pu, Masa-Aki Kakimoto
  • Patent number: 8383304
    Abstract: 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: Grant
    Filed: February 17, 2011
    Date of Patent: February 26, 2013
    Assignee: Ricoh Company, Ltd.
    Inventors: Yoshiki Yanagawa, Masafumi Ohta
  • Publication number: 20120232194
    Abstract: 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: Application
    Filed: August 6, 2010
    Publication date: September 13, 2012
    Inventors: Hitoshi Kondou, Yoshiyuki Sano, Yutaka Tachikawa
  • Publication number: 20110207043
    Abstract: 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: Application
    Filed: February 17, 2011
    Publication date: August 25, 2011
    Inventors: Yoshiki YANAGAWA, Masafumi Ohta
  • Publication number: 20100126377
    Abstract: 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: Application
    Filed: July 3, 2008
    Publication date: May 27, 2010
    Applicant: Nippon Kayaku Kabushiki Kaisha
    Inventors: Takashi Yoneda, Takafumi Fujii, Shinsuke Shimizu, Hirokazu Kitayama
  • Publication number: 20090047585
    Abstract: 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: Application
    Filed: July 6, 2005
    Publication date: February 19, 2009
    Applicant: FUJIFILM Corporation
    Inventors: Nobuo Seto, Yuki Mizukawa, Toru Fujimori
  • Patent number: 7459016
    Abstract: 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: Grant
    Filed: November 27, 2003
    Date of Patent: December 2, 2008
    Assignee: Clariant Produkte (Deutschland) GmbH
    Inventors: Klaus Brychcy, Joachim Weber, Heidrun Mehler
  • Publication number: 20080199732
    Abstract: 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: Application
    Filed: November 28, 2007
    Publication date: August 21, 2008
    Inventors: Tae-Woo Lee, Jong-Jin Park, Lyong-Sun Pu, Masa-Aki Kakimoto
  • Publication number: 20080154032
    Abstract: 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: Application
    Filed: December 21, 2006
    Publication date: June 26, 2008
    Inventor: Jeffrey H. Banning
  • Publication number: 20080146794
    Abstract: 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: Application
    Filed: December 19, 2006
    Publication date: June 19, 2008
    Inventor: Jeffrey H. Banning
  • Publication number: 20080081268
    Abstract: 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: Application
    Filed: August 27, 2007
    Publication date: April 3, 2008
    Applicant: FUJIFILM CORPORATION
    Inventors: Masuji MOTOKI, Yuki MIZUKAWA, Toru FUJIMORI, Hideki TAKAKUWA
  • Patent number: 7326255
    Abstract: 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: Grant
    Filed: November 19, 2003
    Date of Patent: February 5, 2008
    Assignee: L'Oreal S.A.
    Inventors: Alain Lagrange, Sylvain Kravtchenko, Andrew Greaves
  • Patent number: 7018456
    Abstract: 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: Grant
    Filed: March 5, 2003
    Date of Patent: March 28, 2006
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Yoshinori Katoh, Isao Yamaguchi
  • Patent number: 7014696
    Abstract: 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: Grant
    Filed: January 23, 2003
    Date of Patent: March 21, 2006
    Assignee: Avecia Limited
    Inventor: Prakash Patel
  • Publication number: 20040260083
    Abstract: 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: Application
    Filed: June 18, 2004
    Publication date: December 23, 2004
    Inventors: Osamu Shiromaru, Yusaku Ide, Toshio Oshiba, Takuya Kotani
  • Publication number: 20030187250
    Abstract: 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: Application
    Filed: March 6, 2003
    Publication date: October 2, 2003
    Applicant: Canon Kabushiki Kaisha
    Inventors: Takayuki Ishikawa, Teigo Sakakibara, Daisuke Miura, Hidemitsu Uno, Noboru Ono
  • Publication number: 20030180224
    Abstract: 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: Application
    Filed: March 21, 2003
    Publication date: September 25, 2003
    Applicant: PHOTOPHARMICA LIMITED
    Inventors: Stanley Beames Brown, Andrea Lucille Bell, John Griffiths, Jack Schofield
  • Publication number: 20030105321
    Abstract: Compound of formula 1
    Type: Application
    Filed: July 12, 2002
    Publication date: June 5, 2003
    Inventors: Annemarie Wolleb, Heinz Wolleb, Gerardus De Keyzer, Barbara Wagner
  • Publication number: 20020065401
    Abstract: 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: Application
    Filed: November 20, 2001
    Publication date: May 30, 2002
    Inventors: Leonhard Feiler, Zhimin Hao
  • Patent number: 6391505
    Abstract: 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: Grant
    Filed: July 27, 2000
    Date of Patent: May 21, 2002
    Assignee: Kyocera Mita Corporation
    Inventors: Kazunari Hamasaki, Yukimasa Watanabe
  • Patent number: 6365720
    Abstract: 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 aroma
    Type: Grant
    Filed: June 20, 2001
    Date of Patent: April 2, 2002
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Hans-Thomas Schacht, Ramaswami Sreenivasan, Mudaliar Dayal Chandrasekhar, Gilbert Moegle, Barbara Wagner, Charles Edward Monnier
  • Patent number: 6355783
    Abstract: 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: Grant
    Filed: September 7, 2000
    Date of Patent: March 12, 2002
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Leonhard Feiler, Zhimin Hao
  • Patent number: 6323340
    Abstract: 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: Grant
    Filed: July 24, 2000
    Date of Patent: November 27, 2001
    Assignee: Nippon Shobukai Co., Ltd.
    Inventors: Kiyoshi Masuda, Masunori Kitao, Chie Tateyama
  • Patent number: 6281339
    Abstract: 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 hyd
    Type: Grant
    Filed: September 13, 2000
    Date of Patent: August 28, 2001
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Urs Lehmann, Marcel Frick
  • Patent number: 6274728
    Abstract: 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: Grant
    Filed: December 16, 1999
    Date of Patent: August 14, 2001
    Assignee: Ciba Specialty Chemicals Corp.
    Inventors: Véronique Hall-Goulle, Aline Bize
  • Patent number: 6222047
    Abstract: 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: Grant
    Filed: January 13, 1998
    Date of Patent: April 24, 2001
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: John Zambounis, Véronique Hall-Goulle
  • Patent number: 6149722
    Abstract: 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: Grant
    Filed: February 1, 1999
    Date of Patent: November 21, 2000
    Assignee: Zeneca Limited
    Inventors: Colin Dick Robertson, Mark Kenworthy
  • Patent number: 6124451
    Abstract: 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: Grant
    Filed: August 17, 1999
    Date of Patent: September 26, 2000
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Thomas Healy, Cairan Thomas Ewins
  • Patent number: 6090786
    Abstract: 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: Grant
    Filed: February 19, 1997
    Date of Patent: July 18, 2000
    Assignee: 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
  • Patent number: 5817770
    Abstract: 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: Grant
    Filed: March 21, 1997
    Date of Patent: October 6, 1998
    Assignee: Drug Abuse Sciences, Inc.
    Inventors: Jean-Michel Scherrmann, Philippe Pouletty, Herve Galons
  • Patent number: 5789137
    Abstract: 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: Grant
    Filed: May 24, 1996
    Date of Patent: August 4, 1998
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Hisato Itoh, Akio Karasawa, Kenichi Sugimoto
  • Patent number: 5618929
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: April 8, 1997
    Assignee: The Secretary of State for Defence in Her Brittanic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Kenneth J. Harrison, Michael J. Cook, Andrew J. Thomson, Neil B. McKeown, Mervyn F. Daniel, Adrian J. Dunn
  • Patent number: 5618930
    Abstract: 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: Grant
    Filed: March 1, 1996
    Date of Patent: April 8, 1997
    Assignees: Hirofusa Shirai, TDK Corporation
    Inventors: Mutsumi Kimura, Hirofusa Shirai, Toshiki Koyama, Kenji Hanabusa, Yuichi Kubota
  • Patent number: 5516900
    Abstract: 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: Grant
    Filed: September 14, 1994
    Date of Patent: May 14, 1996
    Assignees: Hirofusa Shirai, TDK Corporation
    Inventors: Mutsumi Kimura, Hirofusa Shirai, Toshiki Koyama, Kenji Hanabusa, Yuichi Kubota
  • Patent number: 5359056
    Abstract: 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: Grant
    Filed: July 14, 1992
    Date of Patent: October 25, 1994
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Osamu Kaieda, Takashi Yodoshi, Hideki Itoh, Miho Onozaki
  • Patent number: 5296023
    Abstract: 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: Grant
    Filed: January 4, 1993
    Date of Patent: March 22, 1994
    Assignee: Zeneca Limited
    Inventors: Peter Gregory, Ronald W. Kenyon
  • Patent number: 5250111
    Abstract: 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: Grant
    Filed: April 6, 1992
    Date of Patent: October 5, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert Langley, Michael D. McFarland
  • Patent number: 5229507
    Abstract: 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: Grant
    Filed: November 16, 1990
    Date of Patent: July 20, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Marcus Baumann, Hanspeter Stricker, Walter Fischer, Jurgen Vogt, Jin Mizuguchi
  • Patent number: 5189154
    Abstract: 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: Grant
    Filed: June 28, 1991
    Date of Patent: February 23, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Peter Gregory, Ronald W. Kenyon, Christine Millard
  • Patent number: 5166338
    Abstract: 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: Grant
    Filed: February 13, 1991
    Date of Patent: November 24, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Holger M. Buch, Josef Geisenberger, Hartmut Springer
  • Patent number: 5023325
    Abstract: 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: Grant
    Filed: May 11, 1988
    Date of Patent: June 11, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Peter Aeschlimann
  • Patent number: 4978747
    Abstract: 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: Grant
    Filed: April 13, 1989
    Date of Patent: December 18, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Arnold Weber, Hermann Henk, Klaus Kunde, Jochen Westphal, Klaus Wunderlich
  • Patent number: 4968782
    Abstract: 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: Grant
    Filed: October 13, 1989
    Date of Patent: November 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Peter Aeschlimann
  • Patent number: 4960538
    Abstract: 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: Grant
    Filed: October 20, 1988
    Date of Patent: October 2, 1990
    Assignees: Mitsui Toatsu Chemicals, Inc, Yamamoto Chemicals, Inc.
    Inventors: Hisato Itoh, Takahisa Oguchi, Katashi Enomoto, Masakatsu Nakatsuka, Tsutomu Nishizawa
  • Patent number: 4885360
    Abstract: 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: Grant
    Filed: November 21, 1988
    Date of Patent: December 5, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Scheibli
  • Patent number: 4841028
    Abstract: 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: Grant
    Filed: August 10, 1987
    Date of Patent: June 20, 1989
    Inventors: Peter Aeschlimann, Hansrudolf Schwander
  • Patent number: RE35145
    Abstract: 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: Grant
    Filed: October 25, 1993
    Date of Patent: January 9, 1996
    Assignee: Zeneca Limited
    Inventors: William Stark, Nigel Hughes, Donald M. Gunn