Metal Containing Patents (Class 540/139)
  • Patent number: 9034095
    Abstract: An object is to overcome the drawbacks of conventional blue phthalocyanine pigments upon the formation of images, and to develop a blue pigment that can satisfactorily exhibit a greenish blue color high in chroma and excellent in colorfulness, brightness, dispersibility, hue, tinting power and the like and that is applicable to various image recording methods. The object can be achieved by a greenish blue pigment, which exhibits a greenish blue hue of high chroma and contains a pigment represented by the following formula (I): wherein the number, m, of substituent phthalimidomethyl group(s) is in a range of 1.0?m?5.0, and the number, n, of a substituent sulfonic group R1 is in a range of 0.05?n?1.0.
    Type: Grant
    Filed: July 19, 2012
    Date of Patent: May 19, 2015
    Assignee: DAINICHISEIKA COLOR & CHEMICALS MFG. CO., LTD.
    Inventors: Koji Tsuchiya, Masahiko Aoba, Kenjiro Matsumoto, Takeshi Tamaki
  • Patent number: 8808439
    Abstract: A water-soluble phthalocyanine dye or naphthalocyanine dye with near-infrared absorption comprises at least one complexed unit. Each unit comprises a phthalocyanine or a naphthalocyanine moiety and a metal atom complexed thereto and having a valency of at least three, with two valencies complexed to the phthalocynanine ring or the naphthalocyanine ring, each unit joined to another through a fused ring, at least one valency attached to water-soluble axial ligands. The dyes to may be employed in inkjet inks in conjunction with colorants.
    Type: Grant
    Filed: July 31, 2009
    Date of Patent: August 19, 2014
    Assignee: Hewlett-Packard Development Company, L.P.
    Inventors: Sivapackia Ganapathiappan, Jayprakash Bhatt
  • Patent number: 8784548
    Abstract: A water-soluble phthalocyanine dye or naphthalocyanine dye with near-infrared absorption comprises at least one complexed unit. Each unit comprises a phthalocyanine or a naphthalocyanine moiety and, optionally, a metal atom complexed thereto and, if present, having a valency of from 1 to 5, with two valencies complexed to the phthalocyanine ring or the naphthalocyanine ring. Each unit has two linker moieties on opposite sides or adjacent sides of the unit, wherein water-soluble groups are present on at least one of the linkers, on the metal atom, and optionally on the phthalocyanine or naphthalocyanine moiety.
    Type: Grant
    Filed: July 31, 2009
    Date of Patent: July 22, 2014
    Assignee: Hewlett-Packard Development Company, L.P.
    Inventors: Sivapackia Ganapathiappan, Jayprakash Bhatt
  • Patent number: 8778073
    Abstract: A phthalocyanine dye with extended conjugation includes one or both of a phthalocyanine component and a naphthalocyanine component and at least one water soluble substituent on an aryl group of the phthalocyanine dye. The extended conjugation of the phthalocyanine dye includes at least one benzene moiety of the component being one of (a) joined to an aryl group either indirectly using an alkylene linkage or directly, (b) joined to a benzene moiety of another of the components to form an oligomer of the components, and (c) a combination of (a) and (b). The extended conjugation shifts absorption of the phthalocyanine dye to greater than 800 nm.
    Type: Grant
    Filed: October 30, 2008
    Date of Patent: July 15, 2014
    Assignee: Hewlett-Packard Development Company, L.P.
    Inventors: Sivapackia Ganapathiappan, Zhang-Lin Zhou, Jayprakash C. Bhatt
  • Publication number: 20140170073
    Abstract: A new class of micro- and nano-particulate paramagnetic spin probes especially useful for magnetic resonance imaging techniques, including electron paramagnetic resonance (EPR) and magnetic resonance imaging (MRI). The probes are lithium phthalocyanine derivative compounds. Also provided are suspensions and emulsions comprising lithium phthalocyanine derivative probes. Also provided are noninvasive methods for measuring noninvasive methods of measuring oxygen concentration, oxygen partial pressure, oxygen metabolism, and nitric oxide concentration in a specific tissue, organ, or cell in vivo or in vitro.
    Type: Application
    Filed: August 30, 2013
    Publication date: June 19, 2014
    Applicant: The Ohio State University Research Foundation
    Inventors: Periannan Kuppusamy, Ramasamy P. Pandian, Narasimham L. Parinandi, Jay L. Zweier
  • Patent number: 8686133
    Abstract: The invention provides an oxo-titanylphthalocyanine crystal which is stable, is superior in dispersibility in a photoreceptive layer and efficiently contributes to improvements in sensitivity and charge retention rate of an electrophotographic photoreceptor when it is used as a charge generating agent, a method for producing the oxo-titanylphthalocyanine crystal, and an electrophotographic photoreceptor.
    Type: Grant
    Filed: July 11, 2012
    Date of Patent: April 1, 2014
    Assignee: Kyocera Document Solutions Inc.
    Inventors: Daisuke Kuboshima, Jun Azuma, Yoshio Inagaki, Junichiro Otsubo, Keiji Maruo
  • Patent number: 8658290
    Abstract: The present invention relates to the use of halogenated phthalocyanines as charge transport materials and/or as absorber materials.
    Type: Grant
    Filed: October 31, 2008
    Date of Patent: February 25, 2014
    Assignees: BASF SE, The Board of Trustees of the Leland Stanford Junior University
    Inventors: Martin Koenemann, Sudhakar Sundarraj, Jae Hyung Hwang, Jan Schoeneboom, Albert Liu, Peter Peumans, Felix Eickemeyer, Ingmar Bruder, Neil Gregory Pschirer, Ruediger Sens, Gerd Weber, Sheeja Bahulayan, Peter Erk
  • Patent number: 8608842
    Abstract: An infrared absorbing composition including a compound that is represented by formula (1) and has solubility of 30 mg/mL or less in toluene at 25° C., an organic solvent having a solubility parameter of from 7.3 to 12.1, and a resin is disclosed. In formula (1), each of R1 to R16 independently represents a hydrogen atom or a substituent group, provided that at least one of R1 to R16 represents an R17—X— group or that the compound represented by formula (1) contains at least one condensed-ring structure in which any adjacent two of R1 to R16 form a ring; X represents —S—, —NH—, —NR18—, or —O—; each of R17 and R18 independently represents an aliphatic group or an aryl group; and M represents two atoms selected from the group consisting of hydrogen atoms and monovalent metal atoms, or a divalent metal atom, or a divalent substituted metal atom moiety including a trivalent or tetravalent metal atom and a substituent group.
    Type: Grant
    Filed: May 12, 2011
    Date of Patent: December 17, 2013
    Assignee: FUJIFILM Corporation
    Inventors: Katsumi Kobayashi, Keizo Kimura
  • 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: 8569482
    Abstract: A new class of micro- and nano-particulate paramagnetic spin probes useful for magnetic resonance imaging techniques, including electron paramagnetic resonance (EPR) and magnetic resonance imaging (MRI). The probes are lithium phthalocyanine derivative compounds. Also provided are suspensions and emulsions comprising lithium phthalocyanine derivative probes. Also provided are noninvasive methods for measuring noninvasive methods of measuring oxygen concentration, oxygen partial pressure, oxygen metabolism, and nitric oxide concentration in a specific tissue, organ, or cell in vivo or in vitro.
    Type: Grant
    Filed: November 29, 2011
    Date of Patent: October 29, 2013
    Assignee: The Ohio State University Research Foundation
    Inventors: Periannan Kuppusamy, Vijay Kutala, Jay L. Zweier, Pawel Kwiatkowski
  • Patent number: 8440641
    Abstract: Pharmaceutical compositions of phthalocyanine compounds with a structure according to Formula (I) are described. Phthalocyanines are photosensitizer compounds having a phthalocyanine ring system that can be used for photodynamic therapy. Different phthalocyanines and phthalocyanine salts are shown to have useful characteristics such as water solubility, oil solubility, or tunable photostability. Formulations of phthalocyanines and phthalocyanine salts that can be used for topical and systemic administration are described.
    Type: Grant
    Filed: March 20, 2009
    Date of Patent: May 14, 2013
    Assignee: Case Western Reserve University
    Inventors: Ming Guo, Yun Liu, Malcolm E. Kenney
  • Publication number: 20130008503
    Abstract: Organic photovoltaic (OPV) devices are disclosed. An exemplary device has first and second electrodes and an organic, photovoltaically active zone located between the first and second electrodes. The photovoltaically active zone includes an organic electron-donor material and an organic electron-acceptor material. The electron-donor material includes one or more trivalent- or tetravalent-metal phthalocyanines with alkylchalcogenide ring substituents, and is soluble in at least one organic solvent. This solubility facilitates liquid-processability of the donor material, including formation of thin-films, on an unlimited scale to form planar and bulk heterojunctions in organic OPVs. These donor materials are photovoltaically active in both visible and near-IR wavelengths of light, enabling more of the solar spectrum, for example, to be applied to producing electricity. Also disclosed are methods for producing the metalated phthalocyanines and actual devices.
    Type: Application
    Filed: April 11, 2011
    Publication date: January 10, 2013
    Inventors: Dominic V. McGrath, Mayank Mayukh, Diogenes Placencia, Neal R. Armstrong
  • Patent number: 8346024
    Abstract: A method of initiating a requested action in a computer system via a printed substrate. The substrate has human-readable information and machine-readable coded data printed thereon. The coded data is indicative of a substrate identity and of a plurality of locations on the substrate. The method comprises the steps of: (a) interacting with the substrate using an optically imaging sensing device; (b) imaging the coded data; (c) generating indicating data in the sensing device using the imaged coded data, the indicating data identifying the substrate identity and a position of the sensing device relative to the substrate; and communicating the indicating data to the computer system so that the computer system can initiate the requested action. The coded data is printed with an ink comprising an IR-absorbing naphthalocyanine dye.
    Type: Grant
    Filed: July 28, 2009
    Date of Patent: January 1, 2013
    Assignee: Silverbrook Research Pty Ltd
    Inventors: Simone Charlotte Vonwiller, Damon Donald Ridley, Sutharsiny Indusegaram, Scott Matthew Starling, Graciel Gonzaga, Kia Silverbrook
  • Patent number: 8318005
    Abstract: The present invention relates to making tetra-sulfo iron-phthalocyanine by reacting sulfonated reactant(s) in the presence a boron-containing promoter. The present invention also relates to making tetra-sulfo iron phthalocyanine more tolerant to oxygen by combining the tetra-sulfo iron-phthalocyanine with a stabilizing amount of a complexing agent (e.g., a stabilizing amine) and/or contacting the tetra-sulfo iron-phthalocyanine with steam.
    Type: Grant
    Filed: December 21, 2007
    Date of Patent: November 27, 2012
    Assignee: DOW Global Technologies LLC
    Inventors: John M. Griffin, Stephen A. Bedell, Clare M. Worley
  • Patent number: 8221657
    Abstract: The instant invention relates to novel phthalocyanines and their use as IR-absorbers, in particular in transparent thermoplastic or crosslinkable polymers. A further aspect of the invention is a composition of these phthalocyanines and thermoplastic or crosslinkable polymers and an architectural or automotive glazing containing these phthatolcyanines.
    Type: Grant
    Filed: June 3, 2011
    Date of Patent: July 17, 2012
    Assignee: BASF SE
    Inventors: Francesca Peri, Cesare Lorenzetti, Samanta Cimitan, Markus Grob
  • Patent number: 8206497
    Abstract: Polyphenylated phthalocyanine water-soluble dyes with near-infrared absorption comprise four isoindole units linked together in a large ring to form a phthalocyanine macrocycle, with either four anthracenyl groups or four naphthacenyl groups each linked to an isoindole, and a metal atom optionally complexed to the phthalocyanine macrocycle.
    Type: Grant
    Filed: September 30, 2009
    Date of Patent: June 26, 2012
    Assignee: Hewlett-Packard Development Company, L.P.
    Inventors: Sivapackia Ganapathiappan, Jayprakash Bhatt, Hou Ng
  • Patent number: 8206496
    Abstract: Mixed phthalocyanine and naphthalocyanine water-soluble dyes with near-infrared absorption comprise four isoindole units linked together in a large ring to form a phthalocyanine macrocycle. At least one benzene ring is linked to an isoindole unit and at least one naphthalene ring is linked to another isoindole unit. The remaining two isoindole units each have a benzene ring or a naphthalene ring linked thereto, in any combination. A metal atom is optionally complexed to the phthalocyanine macrocycle.
    Type: Grant
    Filed: September 22, 2009
    Date of Patent: June 26, 2012
    Assignee: Hewlett-Packard Development Company, L.P.
    Inventors: Sivapackia Ganapathiappan, Jayprakash Bhatt
  • Patent number: 8206502
    Abstract: The invention is directed to mixtures of PcTiO and a minor amount of another, substituted titanyl phthalocyanine and the synthesis of mixtures of PcTiO and a minor amount of another, substituted titanyl phthalocyanine. The invention is further directed towards milled pigment compositions of such mixtures, and to use of such milled pigment compositions in an electrophotographic element.
    Type: Grant
    Filed: December 15, 2008
    Date of Patent: June 26, 2012
    Assignee: Eastman Kodak Company
    Inventor: William T. Gruenbaum
  • Patent number: 8202358
    Abstract: Phthalocyanine dyes, naphthalocyanine dyes, and/or bridged phthalocyanine/naphthalocyanine dyes represented by one of the general structures I to XVII, inkjet ink formulation comprising said dyes, and detection systems using said dyes are disclosed and described.
    Type: Grant
    Filed: October 2, 2009
    Date of Patent: June 19, 2012
    Assignee: Hewlett-Packard Development Company, L.P.
    Inventors: Sivapackia Ganapathiappan, Jayprakash C. Bhatt
  • Publication number: 20120137928
    Abstract: A water-soluble phthalocyanine dye or naphthalocyanine dye with near-infrared absorption comprises at least one complexed unit. Each unit comprises a phthalocyanine or a naphthalocyanine moiety and a metal atom complexed thereto and having a valency of at least three, with two valencies complexed to the phthalocynanine ring or the naphthalocyanine ring, each unit joined to another through a fused ring, at least one valency attached to water-soluble axial ligands. The dyes to may be employed in inkjet inks in conjunction with colorants.
    Type: Application
    Filed: July 31, 2009
    Publication date: June 7, 2012
    Inventors: Sivapackia Ganapathiappan, Jayprakash Bhatt
  • Patent number: 8168359
    Abstract: Nano-sized phthalocyanine pigment particles include a phthalocyanine chromogen structure as the main component, and a substituted soluble metal-phthalocyanine dye as a minor component that is associated non-covalently with the phthalocyanine chromogen structure, wherein the presence of one or more sterically bulky substituents on the substituted soluble metal-phthalocyanine dye limits an extent of pigment particle growth and aggregation, to afford nano-sized pigment particles.
    Type: Grant
    Filed: March 25, 2008
    Date of Patent: May 1, 2012
    Assignee: Xerox Corporation
    Inventors: James D. Mayo, Rina Carlini, Adela Goredema, Peter G. Odell, Jeffrey H. Banning
  • Patent number: 8110038
    Abstract: The present invention provides a mixed crystal having absorption properties that are excellent for color reproducibility as a blue pigment, and including a compound represented by the following Formula (I) and a compound represented by the following Formula (II), and a colored pigment dispersion composition including the mixed crystal and a medium. In Formula (I), X represents —SO—Z, —SO2—Z, —SO2NR1R2, —SO3R1, —CONR1R2 or —CO2R1; Z, R1 and R2 each independently represent an alkyl group, an aryl group, a heterocyclic group or the like; Y represents a monovalent substituent; M1 represents a hydrogen atom, a metal element or the like; and a and b are integers from 0 to 16 and satisfy the relationship of 0?a+b?16. In Formula (II), G1 to G4 and Q1 to Q4 each independently represent a carbon atom or a nitrogen atom, and A1 to A4 each independently represent a group of atoms necessary for forming an aromatic ring or heterocycle with the respective G1 to G4 and Q1 to Q4.
    Type: Grant
    Filed: March 27, 2009
    Date of Patent: February 7, 2012
    Assignee: Fujifilm Corporation
    Inventors: Shigeaki Tanaka, Keiichi Tateishi
  • Patent number: 8034531
    Abstract: The present invention relates to a photosensitive resin composition comprising a) as a component (A) a green colorant of the formula (I) in which the rings A, B, C and D are substituted by hydroxy or by moiety wherein R, is hydrogen or C1,-C4.-Alkyl, R2 is hydrogen or C1,-C4-Alkyl, n is 0, 1, 2 or 3 and the ring E is unsubstituted or substituted by C1,-C6alkyl, C1,-C6alkoxy, hydroxy, NHCOR3, NHSO2, R4 or SO2NHR5, wherein R3, is C1,-C4,-Alkyl or phenyl, R4, is C1,-C4-Alkyl or phenyl and R5 is C1,-C4-Alkyl or phenyl, b) as a component (B) an alkali soluble oligomer or polymer (reactive or unreactive), c) as a component (C) a polymerizable monomer, d) as a component (D) a photoinitiator, e) as a component (E) an epoxy compound, and also, if desired, f) as a component (F) further additives, used as solder resist, etching resist or plating resist in the manufacture of printed circuit boards.
    Type: Grant
    Filed: November 19, 2003
    Date of Patent: October 11, 2011
    Assignee: BASF SE
    Inventors: Hidetaka Oka, Jean-Marie Adam
  • Patent number: 7981208
    Abstract: The present invention relates to phthalocyanine compound of poly cross-linking type which is represented with the below formula 1 and is useful for preventing forgery and alternation due to a rapid velocity being responded to a gamma ray of Neutron, and an ink composition comprising it. wherein, M1 and M2 are any one selected from a group consisted of a metal, a metal oxide or a metal halide respectively and may be same or different, R is a hydrogen atom, a halogen atom, a hydroxyl group, an amino group, a hydroxysulfonyl group, an aminosulfonyl group, or an alky group having a substituent group having from 1 to 20 carbon atoms, and n is an integer of 0˜3.
    Type: Grant
    Filed: April 30, 2008
    Date of Patent: July 19, 2011
    Assignees: Nanocms Co., Ltd., Korea Minting and Security Printing Corp.
    Inventors: Shi Surk Kim, Kyung Mi Lee, Ku Won Seo, Sang Geun Lee, Won Gyun Choe, Sun Hong Yoon, Soo Dong Kim
  • Publication number: 20110067597
    Abstract: Mixed phthalocyanine and naphthalocyanine water-soluble dyes with near-infrared absorption comprise four isoindole units linked together in a large ring to form a phthalocyanine macrocycle. At least one benzene ring is linked to an isoindole unit and at least one naphthalene ring is linked to another isoindole unit. The remaining two isoindole units each have a benzene ring or a naphthalene ring linked thereto, in any combination. A metal atom is optionally complexed to the phthalocyanine macrocycle.
    Type: Application
    Filed: September 22, 2009
    Publication date: March 24, 2011
    Inventors: Sivapackia Ganapathiappan, Jayprakash Bhatt
  • Patent number: 7871855
    Abstract: This invention relates to the use of axial substituted phthalocyanine compound as a semiconductor layer between the source/drain electrodes of organic thin-film transistor. The centre ligand of the axial substituted phthalocyanine compound is an atom with 3 valences or higher, and the axial ligands are chlorine, fluorine, or oxygen which can be connected with the centre ligands of axial substituted phthalocyanine compounds. Crystalline Film with high quality can be prepared on an organic substrate from the axial substituted phthalocyanine compound using vapor deposition process. These crystalline films have high carrier mobility, rich energy level, and stable performances and are easy for integrated process. The field effect mobility and the on/off Ratio of the organic thin-film transistor are 0.01 cm2/Vs or more and higher than 105, respectively.
    Type: Grant
    Filed: January 17, 2008
    Date of Patent: January 18, 2011
    Assignee: Changchun Institute of Applied Chemistry Chinese Academy of Sciences
    Inventors: Donghang Yan, De Song, Feng Zhu, Bo Yu
  • Publication number: 20100299849
    Abstract: The present invention relates to a shading process characterized by using a composition comprising a phthalocyanine to which at least one dyestuff is attached through a covalent bonding, to shading compositions, to new compounds used in these shading compositions as well as to the production of these new compounds.
    Type: Application
    Filed: July 21, 2010
    Publication date: December 2, 2010
    Inventors: Alfred HÖHENER, Frank BACHMANN, Adolf KÄSER, Chandrasekhar Dayal MUDALIAR, Dinesh Narendra RELE, Sneha Shankar RANE, Georg ROENTGEN
  • Publication number: 20100240609
    Abstract: Pharmaceutical compositions of phthalocyanine compounds with a structure according to Formula (I) are described. Phthalocyanines are photosensitizer compounds having a phthalocyanine ring system that can be used for photodynamic therapy. Different phthalocyanines and phthalocyanine salts are shown to have useful characteristics such as water solubility, oil solubility, or tunable photostability. Formulations of phthalocyanines and phthalocyanine salts that can be used for topical and systemic administration are described.
    Type: Application
    Filed: March 20, 2009
    Publication date: September 23, 2010
    Applicant: CASE WESTERN RESERVE UNIVERSITY
    Inventors: Ming Guo, Yun Liu, Malcolm E. Kenney
  • Publication number: 20100240885
    Abstract: Provided is a method of manufacturing a phthalocyanine compound denoted by general formula (3). The method comprises conducting a reaction of a compound denoted by general formula (1) or (2) with a metal and/or metal compound in a solvent in the presence of a secondary amine and/or diamine to obtain the phthalocyanine compound denoted by general formula (3). In general formulas (1) and (2), Z denotes an organic group forming a six-membered cyclic aromatic structure with two carbon atoms bonded to Z. In general formula (3), Z is one defined as in general formulas (1) and (2), and M denotes a metal atom belonging to Periods 1 to 4 of Groups 1 to 12.
    Type: Application
    Filed: January 23, 2007
    Publication date: September 23, 2010
    Applicant: FUJIFLIM Corporation
    Inventors: Kazufumi Omura, Shingo Satoh
  • Publication number: 20100172843
    Abstract: A new class of micro- and nano-particulate paramagnetic spin probes especially useful for magnetic resonance imaging techniques, including electron paramagnetic resonance (EPR) and magnetic resonance imaging (MRI). The probes are lithium phthalocyanine derivative compounds. Also provided are suspensions and emulsions comprising lithium phthalocyanine derivative probes. Also provided are noninvasive methods for measuring noninvasive methods of measuring oxygen concentration, oxygen partial pressure, oxygen metabolism, and nitric oxide concentration in a specific tissue, organ, or cell in vivo or in vitro.
    Type: Application
    Filed: January 15, 2010
    Publication date: July 8, 2010
    Applicant: THE OHIO STATE UNIVERSITY RESEARCH FOUNDATION
    Inventors: Periannan Kuppusamy, Ramasamy P. Pandian, Narasimham L. Parinandi, Jay L. Zweier
  • Publication number: 20100113554
    Abstract: A method for the manufacture of a photosensitizing nanomaterial (40) and the products thereof are disclosed. The method for the treatment of a biological target (50) is disclosed. The photosensitizing nanomaterial (40) comprises a metal complex tetrapyrrole derivative (10). The metal complex tetrapyrrole derivative (10) is attached by an axial covalent bond (60) to the surface (25) of a solid nanomaterial (20). The solid nanomaterial (20) has at least one dimension in the nanometre and/or the micrometre range.
    Type: Application
    Filed: November 2, 2009
    Publication date: May 6, 2010
    Inventors: Cristian Alejandro Strassert, Rodrigo Queiroz De Albuquerque, Yolanda Vida, Luisa De Cola
  • Patent number: 7709633
    Abstract: There is provided an aqueous formulation comprising an IR-absorbing naphthalocyanine dye of formula (II): or a salt form thereof, wherein: M is Ga(A1); A1 is an axial ligand selected from —OH, halogen, —OR3, —OC(O)R4 or —O(CH2CH2O)eRe wherein e is an integer from 2 to 10 and Re is H, C1-8 alkyl or C(O)C1-8 alkyl; R1 and R2 may be the same or different and are selected from hydrogen or C1-12 alkoxy; R3 is selected from C1-12 alkyl, C5-12 aryl, C5-12 arylalkyl or Si(Rx)(Ry)(Rz); R4 is selected from C1-12 alkyl, C5-12 aryl or C5-12 arylalkyl; and Rx, Ry and Rz may be the same or different and are selected from C1-12 alkyl, C5-12 aryl, C5-12 arylalkyl, C1-12 alkoxy, C5-12 aryloxy or C5-12 arylalkoxy; The formulation has a pH in the range of 3.5 to 7 and is particularly suitable for use as an IR-absorbing inkjet ink, providing compatibility with known CMYK inks together with an optimally red-shifted ?max.
    Type: Grant
    Filed: July 10, 2006
    Date of Patent: May 4, 2010
    Assignee: Silverbrook Research Pty Ltd
    Inventors: Sutharsiny Indusegaram, Graciel Gonzaga, Simone Charlotte Vonwiller, Scott Matthew Starling, Lachlan Everett Hall, Damon Donald Ridley, Kia Silverbrook
  • Publication number: 20090270610
    Abstract: A naphthalocyanine compound of formula (I): wherein R111, R121, R131 and R141 represent a group of formula (II); R112, R122, R132 and R142 represent a substituent; M1 represents two hydrogen atoms, two monovalent metal atoms, etc.; n112, n122, n132 and n142 are 0 to 4; R211-R218 represent H or a substituent; X211 and X212 represent —O—, —S— or —N(R220)—; R219 and R220 represent H, an aliphatic group, etc.; n211 is 2 or more; and n212 is 1 or more.
    Type: Application
    Filed: December 22, 2006
    Publication date: October 29, 2009
    Applicant: FUJIFILM Corporation
    Inventors: Keizo Kimura, Katsuyoshi Yamakawa
  • Publication number: 20090247742
    Abstract: A method of producing a metal phthalocyanine compound, which contains: conducting a reaction between at least two compounds selected from among Compounds A to F of formula (I), and a metal compound, in a buffer solution of an organic base or an inorganic base and an acid, in the presence of a dehydrating agent: wherein R is a hydrogen atom or a substituent; l is an integer of 0 to 4; a plurality of Rs may be the same or different from each other when l is 2 to 4; and G is a group of atoms necessary for forming at least one of a 5- or 6-membered aromatic ring and a 5- or 6-membered hetero ring.
    Type: Application
    Filed: May 17, 2006
    Publication date: October 1, 2009
    Applicant: FUJIFILM Corporation
    Inventors: Keiichi Tateishi, Masahiko Taniguchi, Hideo Hanawa, Nobuo Seto, Kazufumi Omura
  • Patent number: 7585363
    Abstract: A method for preparing a nanodispersion comprising the steps of: (i) introducing into a milling apparatus a solid fluorinated phthalocycanine pigment according to Formula (I): Wherein M is a metal cation chosen from Groups 1b, 2b, 2a or 3a of the Periodic Table of the Elements; R is fluorine, a perfluoroalkyl or a perfluoroaryl group; z is 1 to 4; L is an anionic ligand; and n is 0 or 1 such that the overall charge on the molecular unit is neutral; followed by milling with agitation the solid fluorinated phthalocyanine in an organic solvent into a suspension of particles so that at least 80 volume % of the particles have a particle size of less than 100 nm.
    Type: Grant
    Filed: October 29, 2008
    Date of Patent: September 8, 2009
    Assignee: Eastman Kodak Company
    Inventors: Tommie L. Royster, Jr., Marina E. Kondakova, Peter G. Bessey
  • Patent number: 7582230
    Abstract: The invention relates to novel liquid crystal displays comprising a broad backlight emission around 530 nm and a green color filter containing a phthalocyanine colorant, most adequately tetrahydroxy- or tetraalkoxy-substituted but lacking solubilizing groups.
    Type: Grant
    Filed: August 5, 2003
    Date of Patent: September 1, 2009
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Gerardus de Keyzer, Taher Yousaf, Vadiraj Subbanna Ekkundi, Chandrasekhar Dayal Mudaliar
  • Patent number: 7550038
    Abstract: Disclosed herein is a novel crosslinked polyphthalocyanine compound. The polyphthalocyanine compound has a structure in which phthalocyanine units are crosslinked to absorb wavelengths in the near-infrared range of 750 to 900 nm, thus being suitable for use as a near-infrared absorber. Further disclosed is a near-infrared absorbing ink composition comprising the polyphthalocyanine compound as a near-infrared absorber.
    Type: Grant
    Filed: June 8, 2006
    Date of Patent: June 23, 2009
    Assignee: CMS Technology Inc.
    Inventors: Shi-surk Kim, Hwal-jong Lee, Kyung-mi Lee
  • Patent number: 7544796
    Abstract: Disclosed is a compound of the formula wherein 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: Grant
    Filed: December 19, 2006
    Date of Patent: June 9, 2009
    Assignee: Xerox Corporation
    Inventor: Jeffrey H. Banning
  • Patent number: 7524367
    Abstract: A poly cross linked phthalocyanine compound for a solar cell and ink composition comprising the same, and more particularly a poly cross linked phthalocyanine compound effective for use in a near infrared absorbent having a high absorption power in a near infrared wavelength from about 750 nm to about 1100 nm, wherein the poly cross linked phthalocyanine compound having structures according to the present inventive concept is sensitized to infrared region, although ruthenium-based compound used for existing dye-sensitized solar cells is sensitized to visible light region, such that the compound according to the present novel concept can be extended in wavelengths for use in solar cells to improve an energy conversion efficiency.
    Type: Grant
    Filed: December 14, 2007
    Date of Patent: April 28, 2009
    Inventors: Dae Woo Ihm, Shi Surk Kim, Kyung Mi Lee, Byung Sun Cho
  • Patent number: 7481954
    Abstract: A composition for a filter material includes a dye and possibly a polymer host. The dye includes a Co(II) compound, a Ni(II) compound or a mixture thereof. Filter material can have a transmittance at 500 nanometers of at least 80% and a steep cutoff absorption band with a transmittance between 600 and 700 nanometers of no more than 10%.
    Type: Grant
    Filed: March 14, 2003
    Date of Patent: January 27, 2009
    Assignee: Rockwell Collins, Inc.
    Inventors: Leslie F. Warren, Jr., Hong-Son Ryang
  • Publication number: 20080311304
    Abstract: Embodiments of the present invention provide an organic photosensitive optoelectronic device comprising at least one nonplanar porphyrin of formula (I), wherein the meanings of M, R and R? are disclosed herein.
    Type: Application
    Filed: June 13, 2007
    Publication date: December 18, 2008
    Inventors: Mark E. THOMPSON, Maria Dolores PEREZ, Carsten BOREK
  • Patent number: 7462711
    Abstract: An object of the present invention is to provide a novel ?-oxo bridged heterometal phthalocyanine compound, and a production method such that the ?-oxo bridged heterometal phthalocyanine compound is obtained simply, selectively and with high yield. The ?-oxo bridged heterometal phthalocyanine compound has a structure in which the central metal atom (M1) in a metal phthalocyanine including M1 as central metal thereof is oxo-bridged with the central metal M2 in a metal phthalocyanine including M2 as central metal thereof.
    Type: Grant
    Filed: June 9, 2003
    Date of Patent: December 9, 2008
    Assignee: Orient Chemical Industries, Ltd.
    Inventors: Kenji Takaki, Yasuhiro Yamasaki
  • 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: 20080194813
    Abstract: Processes for making photosensitive organic pigments for use in imaging members, specifically processes for making a photosensitive phthalocyanine pigments having a specific crystal form, comprising dissolving the pigment in a mixture of a haloacetic acid and alkylene halide to form a solution, precipitating the pigment by adding the solution to a non-solvent system, the solution comprised of one or more organic solvents and a small amount of water, wherein the amount of water controls the crystal form of the pigment, followed by a treatment with a halobenzene to obtain a highly photosensitive second crystal form of the pigment.
    Type: Application
    Filed: February 14, 2007
    Publication date: August 14, 2008
    Applicant: Xerox Corporation
    Inventors: George Liebermann, Marko Saban, Sandra Gardner, Cuong Vong
  • Publication number: 20080194814
    Abstract: Processes for making organic pigments useful in imaging members, specifically for pigments that after further polymorphic conversion may be used in a charge generating layer of an imaging member. More specifically, there are described processes for producing titanyl phthalocyanine (TiOPc) in high yields using tetrahydronaphthalene as reaction solvent, such as TiOPc Type I. This pigment can be successfully converted to a high sensitivity crystal form useful as charge generating pigment in an imaging member.
    Type: Application
    Filed: February 13, 2007
    Publication date: August 14, 2008
    Applicant: Xerox Corporation
    Inventors: Marko D. Saban, George Liebermann, Roger E. Gaynor, Sandra Gardner, Cuong Vong, Evelyn Juandi
  • Patent number: 7332261
    Abstract: A phthalocyanine compound represented by the following general formula (I) and the mixture thereof, and an optical recording medium containing the compound/mixture in its recording layer. wherein in formula (I), M is two hydrogen atoms, a divalent metal atom, a mono-substituted trivalent metal atom, a di-substituted tetravalent metal atom, or an oxymetal, and L1, L2, L3 and L4 are each independently formula (a), formula (b), or formula (c): wherein X, Y, Z and R are defined.
    Type: Grant
    Filed: February 14, 2003
    Date of Patent: February 19, 2008
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Kazuhiro Seino, Shinichi Nakagawa, Tsutami Misawa, Satoshi Kinoshita, Akihiro Kosaka, Hiroshi Terao, Yojiro Kumagae
  • Patent number: 7329315
    Abstract: Phthalocyanine blue pigments and pigment dispersions for water-borne inks and coatings are described. The pigments are produced by dry milling phthalocyanine blue and a polymeric dispersant, optionally with inorganic fillers and other additives, to obtain a material with improved coloristic, rheological, and stability properties. The resulting activated crude is then processed directly into water-based pigment dispersion with additives and/or surfactants to facilitate conversion to pigmentary form while maintaining the desirable green and clean shade.
    Type: Grant
    Filed: December 11, 2006
    Date of Patent: February 12, 2008
    Assignee: Sun Chemical Corporation
    Inventors: Stanislav Vilner, Tatiana N. Romanova, Mark Ortalano, George H. Robertson, Russell J. Schwartz
  • Patent number: 7306660
    Abstract: A cationized supporting material 2 is immersed into a treatment solution containing a level dyeing agent, and then immersed into a treatment solution containing a metal phthalocyanine complex and then dried to thereby obtain an odor eliminating material 1. Alternatively, a cationized supporting material 2 is immersed into a treatment solution containing a metal phthalocyanine complex and a migration inhibitor and then dried to thereby obtain an odor eliminating material 1. The odor eliminating material exerts excellent odor elimination performance against ammonia, hydrogen sulfide, methyl mercaptan, acetic acid and acetaldehyde.
    Type: Grant
    Filed: September 10, 2003
    Date of Patent: December 11, 2007
    Assignee: Suminoe Textile Co., Ltd.
    Inventors: Yasutaro Seto, Tatsuo Nakamura, Yoshiharu Nishino, Shuichi Yonezawa, Shuichi Gennaka
  • Patent number: 7238801
    Abstract: A phthalocyanine compound (1) of a specific structure excelling in ability to absorb near infrared, ability to effect selective absorption of near infrared radiation particularly in a wavelength range exceeding 920 nm and falling short of 1050 nm, solubility in a solvent as well, compatibility with resin, and in such characteristic properties as heat resistance, light resistance, and weatherability, and a near infrared absorbing filter characterized by using the phthalocyanine compound (1) and phthalocyanine compound (2) having a maximum absorption wavelength at least in the range of 800–920 nm are provided. It enjoys a long service life and permits extensive use without selecting a substrate.
    Type: Grant
    Filed: June 10, 2003
    Date of Patent: July 3, 2007
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Kiyoshi Masuda, Masunori Kitao
  • Patent number: 7199237
    Abstract: A flexible organic single crystal has a plurality of columns. The plurality of columns includes a plurality of planar organic compounds arranged so that molecular planes of molecules are respectively parallel to each other. As the organic compound, an organic compound is used that has a large molecular plane and a large area overlapping on an adjacent organic compound due to an intermolecular interaction. Further, energy changes in proportion to a strain. In this structure, when force along the direction of a stack axis is exerted, an angle formed by the stack axis and the normal of the molecular plane of the organic compound changes. Thus, the single crystal obtains flexibility.
    Type: Grant
    Filed: August 31, 2004
    Date of Patent: April 3, 2007
    Assignee: Sony Corporation
    Inventors: Hideo Yamakado, Toshiyuki Kunikiyo, Akito Ugawa