From Reactant Which Contains Plural Cyano Groups (e.g., Preparing From Phthalonitrile, Etc.) Patents (Class 540/143)
  • Patent number: 10640650
    Abstract: The present application can provide a phthalonitrile compound and a use thereof. The phthalonitrile compound has a novel structure, and can exhibit an excellent effect in a use to which the phthalonitrile compound can be applied. An example of the use of the phthalonitrile compound may be a raw material or precursor for, so-called, a phthalonitrile resin, a phthalocyanine dye, a fluorescent whitening agent, a photographic sensitizer, an acid anhydride, or the like.
    Type: Grant
    Filed: December 2, 2016
    Date of Patent: May 5, 2020
    Assignee: LG CHEM, LTD.
    Inventors: Ki Ho Ahn, Sang Woo Kim, Seung Hee Lee
  • Patent number: 8809523
    Abstract: Nanoscale pigment particles of phthalocyanine pigments are prepared by providing a unsubstituted phthalocyanine chromogen material and a substituted phthalocyanine chromogen material, reacting the unsubstituted phthalocyanine chromogen material and the substituted phthalocyanine chromogen material to form a mixture of unsubstituted phthalocyanine dye molecules and substituted phthalocyanine dye molecules, and causing the substituted phthalocyanine dye molecules to non-covalently associate with the unsubstituted phthalocyanine dye molecules, so as to limit an extent of particle growth and aggregation and result in nanoscale pigment particles.
    Type: Grant
    Filed: July 22, 2008
    Date of Patent: August 19, 2014
    Assignee: Xerox Corporation
    Inventors: James D. Mayo, Rina Carlini, C. Geoffrey Allen
  • Publication number: 20140179915
    Abstract: Provided are methods for preparing a phthalocyanine pigment in high yield that eliminate the need to add a heavy metal catalyst. The resulting pigmentary phthalocyanine products thus contain no or only trace amounts of heavy metal impurities. The provided methods produce phthalocyanine pigments that can be used in any application that utilizes phthalocyanine pigments, such as in dispersions, printing inks, paints, plastics and coatings.
    Type: Application
    Filed: January 22, 2014
    Publication date: June 26, 2014
    Applicant: Sun Chemical Corporation
    Inventors: Norman W. Smith, Paul A. Merchak
  • Patent number: 8593713
    Abstract: Disclosed is an ink composition used in an electrowetting display device and an electrowetting display device employing the same. The ink composition used in the electrowetting display device includes a non-polar solvent and a modified hydrophobic pigment, wherein the modified hydrophobic pigment has a structure represented by Formula (I), of P-Gn wherein P is a pigment moiety, n is 1-4 and G is wherein R1 is a straight chain or a branched C4-20 alkyl group, or C5-20 cycloalkyl group.
    Type: Grant
    Filed: July 23, 2012
    Date of Patent: November 26, 2013
    Assignee: Industrial Technology Research Institute
    Inventors: Ming-Tzung Wu, Te-Yi Chang, Chin-Hua Chang, Wen-Jiunn Chen, Yu-Chin Lin, Ching-Mao Wu
  • 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: 8242261
    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: October 1, 2010
    Date of Patent: August 14, 2012
    Assignee: Kyocera Mita Corporation
    Inventors: Daisuke Kuboshima, Jun Azuma, Yoshio Inagaki, Junichiro Otsubo, Keiji Maruo
  • Publication number: 20110311911
    Abstract: Disclosed is a method of proving the authenticity of goods or a support comprising using a compound represented by Formula (I). wherein, in Formula (I), each of R11 to R46 independently represents a hydrogen atom or a substituent group, wherein when a benzene ring is substituted with any of R11 to R46, any groups adjacent to each other among R11 to R46 may be bonded each other to form a ring; M represents a hydrogen atom, a metal ion, or a group containing a metal ion; and n represents 1 or 2. The infrared absorption efficiency is high and the deterioration in infrared absorption over time is ameliorated. The infrared absorption efficiency is high and the deterioration in infrared absorption over time is ameliorated.
    Type: Application
    Filed: December 15, 2009
    Publication date: December 22, 2011
    Inventors: Keizo Kimura, Takuma Amemiya, Katsumi Kobayashi
  • Publication number: 20110073005
    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: Application
    Filed: September 30, 2009
    Publication date: March 31, 2011
    Inventors: Sivapackia Ganapathiappan, Jayprakash Bhatt, Hou Ng
  • Patent number: 7855286
    Abstract: According to the present invention, a titanyl phthalocyanin crystal excellent in storage stability in organic solvents, a method for preparing the same and an electrophotographic photoconductor using the same are provided. In the titanyl phthalocyanin crystal, the method for preparing such a titanyl phthalocyanin crystal and the electrophotographic photoconductor using the same, the titanyl phthalocyanin crystal is characterized by having the maximum peak at a Bragg angle 2?±0.2°=27.2° in a CuK? characteristic X-ray diffraction spectrum and one peak within the range of 270 to 400° C. other than a peak accompanied by the vaporization of adsorbed water in a differential scanning calorimetric analysis.
    Type: Grant
    Filed: October 29, 2009
    Date of Patent: December 21, 2010
    Assignee: Kyocera Mita Corporation
    Inventors: Junichiro Otsubo, Jun Azuma
  • Patent number: 7838670
    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: Grant
    Filed: December 22, 2006
    Date of Patent: November 23, 2010
    Assignee: FUJIFILM Corporation
    Inventors: Keizo Kimura, Katsuyoshi Yamakawa
  • 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: 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
  • Publication number: 20090227785
    Abstract: Nanoscale pigment particles of phthalocyanine pigments are prepared by providing a unsubstituted phthalocyanine chromogen material and a substituted phthalocyanine chromogen material, reacting the unsubstituted phthalocyanine chromogen material and the substituted phthalocyanine chromogen material to form a mixture of unsubstituted phthalocyanine dye molecules and substituted phthalocyanine dye molecules, and causing the substituted phthalocyanine dye molecules to non-covalently associate with the unsubstituted phthalocyanine dye molecules, so as to limit an extent of particle growth and aggregation and result in nanoscale pigment particles.
    Type: Application
    Filed: July 22, 2008
    Publication date: September 10, 2009
    Applicant: XEROX CORPORATION
    Inventors: James D. MAYO, Rina CARLINI, C. Geoffrey ALLEN
  • Patent number: 6472524
    Abstract: Iodogallium phthalocyanine and bromogallium phthalocyanine having novel crystalline forms characterized by X-ray diffraction patterns according to CuK&agr; characteristic X-ray diffraction method and exhibiting excellent sensitivity can be obtained through appropriate selection of a reaction solvent, followed by milling or stirring in an appropriate solvent. For example, &agr;-chloronaphthalene is a suitable solvent for reaction between phthalonitrile and gallium triiodide or tribromide to provide iodogallium phthalocyanine or bromogallium phthalocyanine. Reaction of chlorogallium phthalocyanine or hydroxygallium phthalocyanine with hydroiodic (or hydrobromic) acid is also effective for providing a novel crystal form of iodo- (or bromo-) gallium phthalocyanine. Zirconium phthalocyanine exhibiting good electrophotographic performances can be obtained through a similar process.
    Type: Grant
    Filed: February 9, 2001
    Date of Patent: October 29, 2002
    Assignee: Canon Kabushiki Kaisha
    Inventor: Masato Tanaka
  • 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: 6313288
    Abstract: A mixture is made of a plurality of different titanyltetraazaporphyrin compounds, each of which is represented by formula (1): wherein A, B, C and D are each independently an unsubstituted or substituted benzene ring or pyridine ring, a substituent thereof being selected from the group consisting of nitro group, cyano group, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxyl group having 1 to 8 carbon atoms, and an aryl group. The above-mentioned mixture is contained in a photoconductive layer of an electrophotographic photoconductor as a photoconductive material.
    Type: Grant
    Filed: November 17, 1999
    Date of Patent: November 6, 2001
    Assignee: Ricoh Company, Ltd.
    Inventors: Tomoyuki Shimada, Masayuki Shoshi, Kaoru Tadokoro, Chiaki Tanaka, Michihiko Namba
  • Patent number: 6232466
    Abstract: A process for preparing a stable titanyl phthalocyanine crystal showing at least one diffraction peak at a Bragg angle (2&thgr;±0.2) of 27.3° is disclosed, which comprises treating amorphous or quasi-amorphous titanyl phthalocyanine with a solvent selected from an alcohol solvent, an aromatic solvent, a mixed solvent of an alcohol solvent and an aromatic solvent, or a mixed solvent of an alcohol solvent and water. The resulting titanyl phthalocyanine exhibits high photosensitivity and excellent durability as a photoconductive material of an electrophotographic photoreceptor.
    Type: Grant
    Filed: March 19, 1991
    Date of Patent: May 15, 2001
    Assignee: Fuji Xerox Co., LTD
    Inventors: Katsumi Daimon, Akihiko Tokida, Katsumi Nukada, Hidemi Nukada, Yasuo Sakaguchi
  • Patent number: 6034236
    Abstract: A method for producing a novel phthalocyanine compound which excels in yield and purity, allows no introduction of a chlorine atom into the phthalocyanine skeleton, and possesses relatively bulky substituents is provided. This method is characterized by causing an orthophthalonitrile compound having a substituent exhibiting smaller .sigma..sub.p values than .sigma..sub.m values in the Hammett's rule to react with a metal oxide in the presence of a compound forming in the aqueous solution thereof at 25.degree. C. an acid or conjugate acid having a dissociation index pKa (the logarithmic value of the reciprocal of the dissociation constant of the acid or conjugate acid) of not more than 7.0.
    Type: Grant
    Filed: June 5, 1998
    Date of Patent: March 7, 2000
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Minoru Aoki, Osamu Kaieda
  • Patent number: 5932723
    Abstract: A process for preparing metal-free phthalocyanine by reductive cyclization of phthalonitrile in the presence of an aliphatic alcohol, of a redox catalyst and of an inorganic base comprises effecting the cyclization in the presence of one or more phthalocyanine derivatives selected from the group consisting of phthalocyanine-sulfonic acids and -carboxylic acids and their alkali metal, ammonium and alkylarnozium salts, the amino-substituted and aminomethylated phthalocyanines and their reaction products with alkylating agents, sulfonic acids, sulfonyl chlorides and carbonyl chlorides, the imidomethylene- and amidomethylene-substituted phthalocyanines, the alkyl-, aryl- and cyano-substituted phthalocyanines, the hydroxyl- and alkoxy-substituted phthalocyanines and their reaction products with tetraalkyl- and tetraalkoxy-silanes and the halogenated phthalocyanines.
    Type: Grant
    Filed: December 16, 1997
    Date of Patent: August 3, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Andrea Birgit Schutze, Frank Scherhag, Ingo Klopp, Anette Hartmann
  • Patent number: 5824800
    Abstract: Phthalonitrile, an alkali metal or an alkali metal compound, and a hydrogen donor compound are heated in an organic solvent to synthesize a partially hydrogenated alkali metal phthalocyanine, which is then brought into contact with a dealkalizing agent to effect substitution with hydrogen of the partially hydrogenated alkali metal phthalocyanine to thereby obtain high-purity metal-free phthalocyanine. FX-type metal-free phthalocyanine as obtained according to the foregoing procedure may be used as a charge-generating substance to produce an electrophotographic photoconductor of high image quality which is highly sensitive to near infrared rays.
    Type: Grant
    Filed: June 21, 1996
    Date of Patent: October 20, 1998
    Assignee: Fuji Electric Co., Ltd.
    Inventors: Shinichi Tamura, Seishi Terasaki, Tadashi Mimura, Teruaki Kobayashi, Youichi Tei
  • Patent number: 5817805
    Abstract: A cyan pigment, bis(phthalocyanylalumino)tetraphenyldisiloxane is prepared in a single reaction mixture. A phthalonitrile is reacted at high temperature with an aluminum salt in the presence of an ammonia donor such as urea, in an inert, high boiling organic solvent. The resulting reaction product is cooled and without isolation, refluxed in an aqueous solution of a pyridine compound containing dichlorodiphenylsilane. The desired cyan pigment is then isolated.
    Type: Grant
    Filed: February 21, 1997
    Date of Patent: October 6, 1998
    Assignee: Eastman Kodak Company
    Inventors: William T. Gruenbaum, Chang K. Kim, Cataldo A. Magguilli, Robert J. Opitz
  • Patent number: 5776576
    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: October 7, 1996
    Date of Patent: July 7, 1998
    Assignees: Hirofusa Shirai, TDK Corporation
    Inventors: Mutsumi Kimura, Hirofusa Shirai, Toshiki Koyama, Kenji Hanabusa, Yuichi Kubota
  • Patent number: 5763601
    Abstract: Novel naphthalocyanine compounds are provided including nitro- and amino-substituted naphthalocyanine compounds, and vinyl-containing naphthalocyanine compounds. The compounds have improved solubility and high purity and are expected to find use as photo-functional materials such as dyes. Polymers are obtained using the vinyl-containing naphthalocyanine compounds. The polymers also have improved solubility, high purity, a high naphthalocyanine content and ease of control of the orientation of naphthalocyanine rings and are expected of use as various functional materials.
    Type: Grant
    Filed: February 25, 1997
    Date of Patent: June 9, 1998
    Assignees: Hirofusa Shirai, TDK Corporation
    Inventors: Hirofusa Shirai, Mutsumi Kimura, Yuichi Kubota
  • Patent number: 5668276
    Abstract: A process for the preparation of hydroxygallium phthalocyanines Type A, Type B, Type C, or Type D, which comprises contacting Type V hydroxygallium phthalocyanine with an alcohol.
    Type: Grant
    Filed: July 29, 1996
    Date of Patent: September 16, 1997
    Assignee: Xerox Corporation
    Inventors: Cheng-Kuo Hsiao, Ah-Mee Hor, Sandra J. Gardner, Roger E. Gaynor, Jacques Poitras
  • Patent number: 5656752
    Abstract: A process is described for preparing alkoxy-octasubstituted metal-free or metal-containing naphthalocyanines by etherification of 1,4-dihydroxy-2,3-dicyanonaphthalene and formation of the metal-free naphthalocyanine with or without subsequent metallization.
    Type: Grant
    Filed: September 28, 1995
    Date of Patent: August 12, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Kipper, Bernhard Albert
  • 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: 5585213
    Abstract: A hole-transporting material having excellent hole transportation capability and excellent durability, and an organic EL device and an electrophotographic photoconductive drum for which the above hole-transporting material is adapted and which have excellent stability in the repetitive use.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: December 17, 1996
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Michiko Tamano, Toshikazu Onikubo, Toshio Enokida
  • Patent number: 5556967
    Abstract: Hydroxygallium phthalocyanine crystals are produced by reacting a gallium trihalide with phthalonitrile or diiminoisoindoline in a halogenated aromatic hydrocarbon solvent, treating the resulting halogenated gallium phthalocyanine with an amide solvent, and hydrolyzing the halogenated gallium phthalocyanine. The photoreceptor exhibits stabilized electrophotographic characteristics.
    Type: Grant
    Filed: October 14, 1994
    Date of Patent: September 17, 1996
    Assignee: Fuji Xerox Co., Ltd.
    Inventors: Katsumi Nukada, Katsumi Daimon, Yasuo Sakaguchi, Masakazu Iijima
  • Patent number: 5521306
    Abstract: A process for the preparation of Type V hydroxygallium phthalocyanine which comprises the in situ formation of an alkoxy-bridged gallium phthalocyanine dimer, hydrolyzing said alkoxy-bridged gallium phthalocyanine dimer to hydroxygallium phthalocyanine, and subsequently converting the hydroxygallium phthalocyanine product obtained to Type V hydroxygallium phthalocyanine.
    Type: Grant
    Filed: April 26, 1994
    Date of Patent: May 28, 1996
    Assignee: Xerox Corporation
    Inventors: Richard A. Burt, Cheng-Kuo Hsiao, Dasarao Murti, Roger E. Gaynor, Barkev Keoshkerian, James D. Mayo, George Liebermann
  • Patent number: 5512674
    Abstract: A process for preparing a titanyl phthalocyanine crystal showing at least one diffraction peak at a Bragg angle (2.theta..+-.0.2) of 27.3.degree. is disclosed, which comprises dissolving or suspending titanyl phthalocyanine in concentrated sulfuric acid to form a solution or a slurry and diluting the solution or slurry with an alcohol solvent, an aromatic solvent, a mixed solvent of an alcohol solvent and water, a mixed solvent of an aromatic solvent and water, or a mixed solvent of an alcohol solvent and an aromatic solvent with or without water thereby to precipitate a crystal, and, if desired, treating the precipitated crystal with an alcohol solvent, an aromatic solvent, a mixed solvent of an alcohol solvent and an aromatic solvent or a mixed solvent of an alcohol solvent and/or an aromatic solvent and water. The resulting titanyl phthalocyanine crystal exhibits high photosensitivity and excellent durability as a photoconductive material of an electrophotographic photoreceptor.
    Type: Grant
    Filed: December 6, 1993
    Date of Patent: April 30, 1996
    Assignee: Fuji Xerox Co., Ltd.
    Inventors: Hidemi Nukada, Akihiko Tokida, Yasuo Sakaguchi, Katsumi Daimon, Katsumi Nukada
  • Patent number: 5494767
    Abstract: Disclosed are a phthalocyanine composition which comprises having main diffraction peaks at 7.5.degree., 22.5.degree., 24.3.degree., 25.3.degree. and 28.6.degree. of Bragg angles (2.theta..+-.0.2.degree.) in an X-ray diffraction spectrum with Cu K.alpha., a process for preparing the same, an electrophotographic photoreceptor using the same and a coating solution for a charge generation layer containing the same.
    Type: Grant
    Filed: January 25, 1994
    Date of Patent: February 27, 1996
    Assignee: Hitachi Chemical Company Co., Ltd.
    Inventors: Mikio Itagaki, Shigeru Hayashida, Megumi Matsui, Hiroko Ishikawa, Yoshii Morishita, Takayuki Akimoto
  • Patent number: 5493016
    Abstract: A process for the preparation of alkoxy-bridged metallophthalocyanine dimers by the reaction of a trivalent metal compound with ortho-phthalodinitrile or 1,3-diiminoisoindoline in the presence of a diol.
    Type: Grant
    Filed: April 26, 1994
    Date of Patent: February 20, 1996
    Assignee: Xerox Corporation
    Inventors: Richard A. Burt, George Liebermann, Gordon K. Hamer, Sandra J. Gardner, Carol A. Jennings, Katsumi Daimon, Katsumi Nukada
  • Patent number: 5463044
    Abstract: A process for preparing chlorogallium phthalocyanine comprising the steps of: reacting gallium trichloride and phthalonitrile or diiminoisoindoline in an aromatic hydrocarbon solvent; and treating the resulting chlorogallium phthalocyanine with a second solvent different from the aromatic hydrocarbon solvent.
    Type: Grant
    Filed: August 18, 1993
    Date of Patent: October 31, 1995
    Assignee: Fuji Xerox Co., Ltd.
    Inventors: Katsumi Nukada, Akira Imai, Masakazu Iijima
  • Patent number: 5430143
    Abstract: A process is described for preparing metal phthalocyanines by reacting orthodinitriles dissolved or suspended in organic solvents or pulverulent mixtures of ortho-dinitriles with anhydrous ammine-metal carboxylate salts or metal-aminocarboxylic acid complexes without alkaline or chloride-containing additaments using an ortho-dinitrile excess of from 0.1 to 5% by weight.
    Type: Grant
    Filed: October 13, 1993
    Date of Patent: July 4, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Joachim Kranz, Wolfgang Habermann
  • Patent number: 5420268
    Abstract: A layered photoconductive imaging member comprised of a supporting substrate, a photogenerating layer and a charge transport layer, and wherein the photogenerating layer contains Type IV oxytitanium phthalocyanine obtained by a process which comprises the hydrolysis of a dihalotitanium phthalocyanine in a strong acid.
    Type: Grant
    Filed: May 27, 1993
    Date of Patent: May 30, 1995
    Assignee: Xerox Corporation
    Inventors: Denis Desilets, Terry L. Bluhm, Cheng-Kuo Hsiao
  • Patent number: 5405954
    Abstract: Disclosed is a process for the preparation of chloroindium phthalocyanine which comprises heating a mixture of indium trichloride and ortho-phthalodinitrile in a mixture of solvents comprised of a dialkylaminoalkanol and a high boiling second solvent; and cooling the mixture to enable precipitation.
    Type: Grant
    Filed: June 18, 1993
    Date of Patent: April 11, 1995
    Assignee: Xerox Corporation
    Inventors: George Liebermann, Roger E. Gaynor, Ah-Mee Hor, Charles G. Allen
  • Patent number: 5384397
    Abstract: The invention includes a water-soluble oxygen carrier. The oxygen carrier includes a meso-.alpha.,.alpha.,.alpha.,.alpha.-tetrakis(o-propanoylamino)phenylporph yrin, in which the 3-carbons of the propanoyl groups are each covalently bound to an amine nitrogen, and iron or cobalt is bound to the pyrrole nitrogens of the porphyrin. The oxygen carrier also includes a ligand L for protecting the open face of the porphyrin from .mu.-oxo dimer formation.
    Type: Grant
    Filed: November 9, 1993
    Date of Patent: January 24, 1995
    Assignee: The Board of Trustees of the Leland Stanford Junior University
    Inventors: Xumu Zhang, Erich Uffelman, James P. Collman
  • Patent number: 5350844
    Abstract: A process for the preparation of a more perfect crystalline form of the Type I polymorph of titanyl phthalocyanine which comprises dissolving a precursor titanyl phthalocyanine Type I in a solution of trihaloacetic acid and alkylene chloride; adding the resultant solution to a solvent thereby enabling precipitation of Type X titanyl phthalocyanine; separating the titanyl phthalocyanine Type X from the solution; followed by a first washing with an organic solvent and a second washing with water; slurrying the resulting Type X titanyl phthalocyanine in an organic solvent enabling conversion of said Type X to Type IV titanyl phthalocyanine; and thereafter, subjecting the Type IV titanyl phthalocyanine obtained to treatment with an organic solvent to enable said crystalline form of titanyl phthalocyanine Type I.
    Type: Grant
    Filed: March 1, 1993
    Date of Patent: September 27, 1994
    Assignee: Xerox Corporation
    Inventors: Trevor I. Martin, James D. Mayo, Nancy A. Listigovers, Cheng K. Hsiao, Terry L. Bluhm, Sharon E. Normandin, Kathleen M. Carmichael
  • Patent number: 5334856
    Abstract: An image readout device having a plurality of readout elements for converting image into electrical signals, each element having a photoconductive layer and a pair of electrodes which contact the photoconductive layer, and between which the layer is disposed. The photoconductive layer contains a charge generation material and a charge transport material. Oxytitanium phthalocyanine is used as the charge generation material.
    Type: Grant
    Filed: July 28, 1993
    Date of Patent: August 2, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Shigenori Otsuka, Hiromi Horiuchi, Masayuki Hiroi
  • Patent number: 5334714
    Abstract: There is here disclosed a method for preparing an alkoxyphthalocyanine represented by the formula (1): ##STR1## wherein each of Rs is independently a secondary alkyl group having 3 to 20 carbon atoms, Met is a divalent metal atom or an oxy metal, and the substitution positions of -ORs are the 1- or 4-position, the 5- or 8-position, the 9- or 12 position, and the 13- or 16-position, which comprises the steps of heating a mixture of 3-alkoxyphthalonitrile and an organic base in an alcohol to 90.degree.-120.degree. C., adding a metal derivative at the same temperature, and then carrying out reaction, or alternatively the step of reacting a mixture of a 1,3-diimino-4-alkoxyisoindoline and a metal derivative in the presence or absence of an organic base in an aliphatic alcohol having 6 or more carbon atoms. In addition, the ratio of isomers of the alkoxyphthalocyanine can be controlled by regulating the addition time of the organic base.
    Type: Grant
    Filed: March 2, 1993
    Date of Patent: August 2, 1994
    Assignees: Mitsui Toatsu Chemicals, Incorporated, Yamamoto Chemicals, Incorporated
    Inventors: Takahisa Oguchi, Kenichi Sugimoto, Shin Aihara, Hisato Itoh, Mansuke Matsumoto, Toshihiro Masaoka, Masakazu Nakamura
  • Patent number: 5290928
    Abstract: A process for preparing an oxytitanium phthalocyanine hydrate crystal which, when dried at 100.degree. C. and 0.1 mmHg for 8 hours and then allowed to stand in air at room temperature for 12 hours, has a structural formula of TiOPc.multidot.(H.sub.2 O).sub.n, wherein Pc represents a phthalocyanine nucleus, and n represents a number of from 0.15 to 1, and elemental analysis values of C: 65.0 to 66.3%, H: 2.5 to 3.1%, and N: 18.5 to 19.3% is disclosed, which process comprises the steps of: mechanically grinding a mixture of oxytitanium phthalocyanine and an inorganic salt to convert the crystal form of the oxytitanium phthalocyanine to a crystal form showing a distinct peak in its X-ray diffraction pattern at a Bragg angle (2.theta..+-.0.2.degree. ) of 27.3.degree. and treating the resulting oxytitanium phthalocyanine crystal with a mixed solvent of water and a water-insoluble organic solvent.
    Type: Grant
    Filed: August 12, 1992
    Date of Patent: March 1, 1994
    Assignee: Fuji Xerox Co., Ltd.
    Inventors: Katsumi Nukada, Masakazu Iijima, Akira Imai, Katsumi Daimon
  • Patent number: 5270463
    Abstract: A method for preparing a halogenated alkoxyphthalocyanine represented by the formula (7) ##STR1## wherein R.sup.3 to R.sup.6 may be different and each of them is a secondary alkyl group, X is a halogen atom, n is the number of X and in the range of from 1 to 4, and Met is two hydrogen atoms, a divalent metal atom, or a trivalent or a tetravalent metallic derivative, which comprises the step of reacting a metal or a metallic compound with one to four kinds of raw materials selected from the group consisting of phthalonitriles represented by the following formula (1) and diiminoisoindolines represented by the following formula (2) ##STR2## wherein R.sup.1 is a secondary alkyl group, X is a halogen atom, and each of p and q is 0 or 1, but in at least one raw material, p or q is 1, and halogenated alkoxyphthalocyanine prepared by said method.
    Type: Grant
    Filed: July 1, 1991
    Date of Patent: December 14, 1993
    Assignees: Mitsui Toatsu Chemicals, Incorporated, Yamamoto Chemicals, Incorporated
    Inventors: Hisato Itoh, Katashi Enomoto, Takahisa Oguchi, Tutomu Nishizawa
  • Patent number: 5220010
    Abstract: There is here disclosed a method for preparing an alkoxyphthalocyanine represented by the formula (1): ##STR1##
    Type: Grant
    Filed: December 24, 1991
    Date of Patent: June 15, 1993
    Assignees: Mitsui Toatsu Chemicals, Incorporated, Yamamoto Chemicals, Incorporated
    Inventors: Takahisa Oguchi, Kenichi Sugimoto, Shin Athara, Hisato Itoh, Mansuke Matsumoto, Toshihiro Masaoka, Masakazu Nakamura
  • Patent number: 5206359
    Abstract: A process for the preparation of titanyl phthalocyanine which comprises the treatment of titanyl phthalocyanine Type X with a halobenzene.
    Type: Grant
    Filed: April 11, 1991
    Date of Patent: April 27, 1993
    Assignee: Xerox Corporation
    Inventors: James D. Mayo, James M. Duff, Trevor I. Martin, Terry L. Bluhm, Cheng K. Hsiao, Ah-Mee Hor
  • Patent number: 5192788
    Abstract: Compositions for the treatment or prevention of AIDS or other diseases resulting from infection with the Human Immunodeficiency Virus containing one or more porphyrins.Porphyrins are tetrapyrrole macrocyle compounds with bridges of one carbon joining the pyrroles. Porphyrins occur naturally and are made synthetically. Derivatives of porphyrins include porphyrins with one or more substituents on one or more of the rings, porphyrins in which the conjugation of the ring has been altered by addition of substituents, porphyrins in which one or more center nitrogens is attached to substituents such as metals, liganded metals, and organic moieties, metalloporphyrins and metalloporphyrin-ligand complexes.Examples of natural and synthetic, positively, negatively, and neutrally charged porphyrins and porphyrin derivatives have been found to exhibit selective anti-HIV activity which is not dependent on the presence of light.
    Type: Grant
    Filed: May 23, 1988
    Date of Patent: March 9, 1993
    Assignees: Georgia State University Foundation, Inc., Emory University
    Inventors: Dabney W. Dixon, Raymond F. Schinazi, Luigi G. Marzilli
  • Patent number: 5189156
    Abstract: A process for the preparation of titanyl phthalocyanine which comprises the reaction of a titanium tetraalkoxide and diiminoisoindolene in the presence of a halonaphthalene solvent; dissolving the resulting Type I titanyl phthalocyanine in a haloacetic acid and an alkylene halide; adding the resulting mixture slowly to a cold alcohol solution; and thereafter isolating the resulting Type X titanyl phthalocyanine with an average volume particle size diameter of from about 0.02 to about 0.5 micron.
    Type: Grant
    Filed: April 1, 1991
    Date of Patent: February 23, 1993
    Assignee: Xerox Corporation
    Inventors: James D. Mayo, Sandra J. Gardner
  • Patent number: 5189155
    Abstract: A process for the preparation of titanyl phthalocyanine Type I which comprises the reaction of titanium tetraalkoxide and diminoisoindolene in the presence of a halonaphthalene solvent.
    Type: Grant
    Filed: April 11, 1991
    Date of Patent: February 23, 1993
    Assignee: Xerox Corporation
    Inventors: James D. Mayo, Terry L. Bluhm, Cheng K. Hsiao, Trevor I. Martin, Ah-Mee Hor
  • Patent number: 5183886
    Abstract: A process for the preparation of crystalline oxytitanium phthalocyanine comprising contacting dichlorotitanium phthalocyanine, dibromotitanium phthalocyanine or a mixture of them with at least one organic solvent selected from the group consisting of aromatic nitro compounds, nitrogen-containing cyclic ethers, aromatic amines, alcohols containing not less than 4 carbon atoms, aldehydes, ketones, lactones, lactams, acid amides, nitriles, alkyl sulfoxides, substituted phenols and non-substituted phenols in association with water.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: February 2, 1993
    Assignee: Mitsubishi Kasei Corporation
    Inventor: Iwao Takagishi
  • Patent number: 5182382
    Abstract: A process for the preparation of titanyl phthalocyanine Type X which comprises dissolving titanyl phthalocyanine Type I in a solution of trifluoroacetic acid and methylene chloride; adding the resultant solution to a solvent enabling precipitation of Type X titanyl phthalocyanine; separating the titanyl phthalocyanine Type X from the solution; followed by a first washing with an organic solvent and a second washing with water; and thereafter a solvent treatment with fluorobenzene.
    Type: Grant
    Filed: May 28, 1991
    Date of Patent: January 26, 1993
    Assignee: Xerox Corporation
    Inventors: James D. Mayo, James M. Duff, Terry L. Bluhm, Cheng K. Hsiao
  • Patent number: 5164493
    Abstract: A process for the preparation of titanyl phthalocyanine which comprises the reaction in a solvent of phthalonitrile and diiminoisoindoline with titanium tetraalkoxide.
    Type: Grant
    Filed: February 28, 1991
    Date of Patent: November 17, 1992
    Assignee: Xerox Corporation
    Inventors: James D. Mayo, James M. Duff