From Reactant Which Contains Plural Cyano Groups (e.g., Preparing From Phthalonitrile, Etc.) Patents (Class 540/143)
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Patent number: 10640650Abstract: 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: GrantFiled: December 2, 2016Date of Patent: May 5, 2020Assignee: LG CHEM, LTD.Inventors: Ki Ho Ahn, Sang Woo Kim, Seung Hee Lee
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Patent number: 8809523Abstract: 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: GrantFiled: July 22, 2008Date of Patent: August 19, 2014Assignee: Xerox CorporationInventors: James D. Mayo, Rina Carlini, C. Geoffrey Allen
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Publication number: 20140179915Abstract: 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: ApplicationFiled: January 22, 2014Publication date: June 26, 2014Applicant: Sun Chemical CorporationInventors: Norman W. Smith, Paul A. Merchak
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Patent number: 8593713Abstract: 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: GrantFiled: July 23, 2012Date of Patent: November 26, 2013Assignee: Industrial Technology Research InstituteInventors: Ming-Tzung Wu, Te-Yi Chang, Chin-Hua Chang, Wen-Jiunn Chen, Yu-Chin Lin, Ching-Mao Wu
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Publication number: 20130008503Abstract: 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: ApplicationFiled: April 11, 2011Publication date: January 10, 2013Inventors: Dominic V. McGrath, Mayank Mayukh, Diogenes Placencia, Neal R. Armstrong
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Patent number: 8242261Abstract: 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: GrantFiled: October 1, 2010Date of Patent: August 14, 2012Assignee: Kyocera Mita CorporationInventors: Daisuke Kuboshima, Jun Azuma, Yoshio Inagaki, Junichiro Otsubo, Keiji Maruo
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Publication number: 20110311911Abstract: 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: ApplicationFiled: December 15, 2009Publication date: December 22, 2011Inventors: Keizo Kimura, Takuma Amemiya, Katsumi Kobayashi
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Publication number: 20110073005Abstract: 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: ApplicationFiled: September 30, 2009Publication date: March 31, 2011Inventors: Sivapackia Ganapathiappan, Jayprakash Bhatt, Hou Ng
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Patent number: 7855286Abstract: 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: GrantFiled: October 29, 2009Date of Patent: December 21, 2010Assignee: Kyocera Mita CorporationInventors: Junichiro Otsubo, Jun Azuma
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Patent number: 7838670Abstract: 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: GrantFiled: December 22, 2006Date of Patent: November 23, 2010Assignee: FUJIFILM CorporationInventors: Keizo Kimura, Katsuyoshi Yamakawa
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Publication number: 20100240885Abstract: 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: ApplicationFiled: January 23, 2007Publication date: September 23, 2010Applicant: FUJIFLIM CorporationInventors: Kazufumi Omura, Shingo Satoh
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Publication number: 20090247742Abstract: 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: ApplicationFiled: May 17, 2006Publication date: October 1, 2009Applicant: FUJIFILM CorporationInventors: Keiichi Tateishi, Masahiko Taniguchi, Hideo Hanawa, Nobuo Seto, Kazufumi Omura
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Publication number: 20090227785Abstract: 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: ApplicationFiled: July 22, 2008Publication date: September 10, 2009Applicant: XEROX CORPORATIONInventors: James D. MAYO, Rina CARLINI, C. Geoffrey ALLEN
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Patent number: 6472524Abstract: 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: GrantFiled: February 9, 2001Date of Patent: October 29, 2002Assignee: Canon Kabushiki KaishaInventor: Masato Tanaka
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Patent number: 6323340Abstract: A phthalocyanine compound is provided which exhibits particularly high transmittance to a visible ray, offers a highly efficient cut of a near infrared ray, excels in the ability to effect selective absorption in a near infrared region, excels in the solubility in a solvent, excels in the compatibility with a resin, and excels in heat resistance, light resistance, and weatherability, a method for the production thereof, a near infrared absorbable dye using the same, and a heat ray shielding material, a plasma display grade filter and a near infrared absorbable material formed thereof.Type: GrantFiled: July 24, 2000Date of Patent: November 27, 2001Assignee: Nippon Shobukai Co., Ltd.Inventors: Kiyoshi Masuda, Masunori Kitao, Chie Tateyama
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Patent number: 6313288Abstract: 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: GrantFiled: November 17, 1999Date of Patent: November 6, 2001Assignee: Ricoh Company, Ltd.Inventors: Tomoyuki Shimada, Masayuki Shoshi, Kaoru Tadokoro, Chiaki Tanaka, Michihiko Namba
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Patent number: 6232466Abstract: 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: GrantFiled: March 19, 1991Date of Patent: May 15, 2001Assignee: Fuji Xerox Co., LTDInventors: Katsumi Daimon, Akihiko Tokida, Katsumi Nukada, Hidemi Nukada, Yasuo Sakaguchi
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Patent number: 6034236Abstract: 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: GrantFiled: June 5, 1998Date of Patent: March 7, 2000Assignee: Nippon Shokubai Co., Ltd.Inventors: Minoru Aoki, Osamu Kaieda
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Patent number: 5932723Abstract: 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: GrantFiled: December 16, 1997Date of Patent: August 3, 1999Assignee: BASF AktiengesellschaftInventors: Andrea Birgit Schutze, Frank Scherhag, Ingo Klopp, Anette Hartmann
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Patent number: 5824800Abstract: 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: GrantFiled: June 21, 1996Date of Patent: October 20, 1998Assignee: Fuji Electric Co., Ltd.Inventors: Shinichi Tamura, Seishi Terasaki, Tadashi Mimura, Teruaki Kobayashi, Youichi Tei
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Patent number: 5817805Abstract: 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: GrantFiled: February 21, 1997Date of Patent: October 6, 1998Assignee: Eastman Kodak CompanyInventors: William T. Gruenbaum, Chang K. Kim, Cataldo A. Magguilli, Robert J. Opitz
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Patent number: 5776576Abstract: A novel phthalocyanine compound having improved solubility and high purity and containing a polymerizable vinyl group within its molecule is provided. Intermediates to this phthalocyanine compound also have improved solubility and high purity. Further, with the novel phthalocyanine compound used as a starting monomer, a novel polymer is obtained which has a high content of (metal) phthalocyanine and is easy to control the orientation of phthalocyanine rings. The polymer having improved solubility and high purity is expected of use as functional material such as catalysts and recording material.Type: GrantFiled: October 7, 1996Date of Patent: July 7, 1998Assignees: Hirofusa Shirai, TDK CorporationInventors: Mutsumi Kimura, Hirofusa Shirai, Toshiki Koyama, Kenji Hanabusa, Yuichi Kubota
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Patent number: 5763601Abstract: 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: GrantFiled: February 25, 1997Date of Patent: June 9, 1998Assignees: Hirofusa Shirai, TDK CorporationInventors: Hirofusa Shirai, Mutsumi Kimura, Yuichi Kubota
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Patent number: 5668276Abstract: 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: GrantFiled: July 29, 1996Date of Patent: September 16, 1997Assignee: Xerox CorporationInventors: Cheng-Kuo Hsiao, Ah-Mee Hor, Sandra J. Gardner, Roger E. Gaynor, Jacques Poitras
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Patent number: 5656752Abstract: 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: GrantFiled: September 28, 1995Date of Patent: August 12, 1997Assignee: BASF AktiengesellschaftInventors: Juergen Kipper, Bernhard Albert
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Patent number: 5618930Abstract: A novel phthalocyanine compound having improved solubility and high purity and containing a polymerizable vinyl group within its molecule is provided. Intermediates to this phthalocyanine compound also have improved solubility and high purity. Further, with the novel phthalocyanine compound used as a starting monomer, a novel polymer is obtained which has a high content of (metal) phthalocyanine and is easy to control the orientation of phthalocyanine rings. The polymer having improved solubility and high purity is expected of use as functional material such as catalysts and recording material.Type: GrantFiled: March 1, 1996Date of Patent: April 8, 1997Assignees: Hirofusa Shirai, TDK CorporationInventors: Mutsumi Kimura, Hirofusa Shirai, Toshiki Koyama, Kenji Hanabusa, Yuichi Kubota
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Patent number: 5585213Abstract: 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: GrantFiled: June 6, 1995Date of Patent: December 17, 1996Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Michiko Tamano, Toshikazu Onikubo, Toshio Enokida
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Patent number: 5556967Abstract: 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: GrantFiled: October 14, 1994Date of Patent: September 17, 1996Assignee: Fuji Xerox Co., Ltd.Inventors: Katsumi Nukada, Katsumi Daimon, Yasuo Sakaguchi, Masakazu Iijima
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Patent number: 5521306Abstract: 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: GrantFiled: April 26, 1994Date of Patent: May 28, 1996Assignee: Xerox CorporationInventors: Richard A. Burt, Cheng-Kuo Hsiao, Dasarao Murti, Roger E. Gaynor, Barkev Keoshkerian, James D. Mayo, George Liebermann
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Patent number: 5512674Abstract: 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: GrantFiled: December 6, 1993Date of Patent: April 30, 1996Assignee: Fuji Xerox Co., Ltd.Inventors: Hidemi Nukada, Akihiko Tokida, Yasuo Sakaguchi, Katsumi Daimon, Katsumi Nukada
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Patent number: 5494767Abstract: 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: GrantFiled: January 25, 1994Date of Patent: February 27, 1996Assignee: Hitachi Chemical Company Co., Ltd.Inventors: Mikio Itagaki, Shigeru Hayashida, Megumi Matsui, Hiroko Ishikawa, Yoshii Morishita, Takayuki Akimoto
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Patent number: 5493016Abstract: 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: GrantFiled: April 26, 1994Date of Patent: February 20, 1996Assignee: Xerox CorporationInventors: Richard A. Burt, George Liebermann, Gordon K. Hamer, Sandra J. Gardner, Carol A. Jennings, Katsumi Daimon, Katsumi Nukada
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Patent number: 5463044Abstract: 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: GrantFiled: August 18, 1993Date of Patent: October 31, 1995Assignee: Fuji Xerox Co., Ltd.Inventors: Katsumi Nukada, Akira Imai, Masakazu Iijima
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Patent number: 5430143Abstract: 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: GrantFiled: October 13, 1993Date of Patent: July 4, 1995Assignee: BASF AktiengesellschaftInventors: Joachim Kranz, Wolfgang Habermann
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Patent number: 5420268Abstract: 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: GrantFiled: May 27, 1993Date of Patent: May 30, 1995Assignee: Xerox CorporationInventors: Denis Desilets, Terry L. Bluhm, Cheng-Kuo Hsiao
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Patent number: 5405954Abstract: 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: GrantFiled: June 18, 1993Date of Patent: April 11, 1995Assignee: Xerox CorporationInventors: George Liebermann, Roger E. Gaynor, Ah-Mee Hor, Charles G. Allen
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Patent number: 5384397Abstract: 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: GrantFiled: November 9, 1993Date of Patent: January 24, 1995Assignee: The Board of Trustees of the Leland Stanford Junior UniversityInventors: Xumu Zhang, Erich Uffelman, James P. Collman
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Patent number: 5350844Abstract: 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: GrantFiled: March 1, 1993Date of Patent: September 27, 1994Assignee: Xerox CorporationInventors: Trevor I. Martin, James D. Mayo, Nancy A. Listigovers, Cheng K. Hsiao, Terry L. Bluhm, Sharon E. Normandin, Kathleen M. Carmichael
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Patent number: 5334856Abstract: 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: GrantFiled: July 28, 1993Date of Patent: August 2, 1994Assignee: Mitsubishi Kasei CorporationInventors: Shigenori Otsuka, Hiromi Horiuchi, Masayuki Hiroi
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Patent number: 5334714Abstract: 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: GrantFiled: March 2, 1993Date of Patent: August 2, 1994Assignees: Mitsui Toatsu Chemicals, Incorporated, Yamamoto Chemicals, IncorporatedInventors: Takahisa Oguchi, Kenichi Sugimoto, Shin Aihara, Hisato Itoh, Mansuke Matsumoto, Toshihiro Masaoka, Masakazu Nakamura
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Patent number: 5290928Abstract: 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: GrantFiled: August 12, 1992Date of Patent: March 1, 1994Assignee: Fuji Xerox Co., Ltd.Inventors: Katsumi Nukada, Masakazu Iijima, Akira Imai, Katsumi Daimon
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Patent number: 5270463Abstract: 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: GrantFiled: July 1, 1991Date of Patent: December 14, 1993Assignees: Mitsui Toatsu Chemicals, Incorporated, Yamamoto Chemicals, IncorporatedInventors: Hisato Itoh, Katashi Enomoto, Takahisa Oguchi, Tutomu Nishizawa
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Patent number: 5220010Abstract: There is here disclosed a method for preparing an alkoxyphthalocyanine represented by the formula (1): ##STR1##Type: GrantFiled: December 24, 1991Date of Patent: June 15, 1993Assignees: Mitsui Toatsu Chemicals, Incorporated, Yamamoto Chemicals, IncorporatedInventors: Takahisa Oguchi, Kenichi Sugimoto, Shin Athara, Hisato Itoh, Mansuke Matsumoto, Toshihiro Masaoka, Masakazu Nakamura
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Patent number: 5206359Abstract: A process for the preparation of titanyl phthalocyanine which comprises the treatment of titanyl phthalocyanine Type X with a halobenzene.Type: GrantFiled: April 11, 1991Date of Patent: April 27, 1993Assignee: Xerox CorporationInventors: James D. Mayo, James M. Duff, Trevor I. Martin, Terry L. Bluhm, Cheng K. Hsiao, Ah-Mee Hor
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Patent number: 5192788Abstract: 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: GrantFiled: May 23, 1988Date of Patent: March 9, 1993Assignees: Georgia State University Foundation, Inc., Emory UniversityInventors: Dabney W. Dixon, Raymond F. Schinazi, Luigi G. Marzilli
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Patent number: 5189156Abstract: 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: GrantFiled: April 1, 1991Date of Patent: February 23, 1993Assignee: Xerox CorporationInventors: James D. Mayo, Sandra J. Gardner
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Patent number: 5189155Abstract: 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: GrantFiled: April 11, 1991Date of Patent: February 23, 1993Assignee: Xerox CorporationInventors: James D. Mayo, Terry L. Bluhm, Cheng K. Hsiao, Trevor I. Martin, Ah-Mee Hor
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Patent number: 5183886Abstract: 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: GrantFiled: May 22, 1992Date of Patent: February 2, 1993Assignee: Mitsubishi Kasei CorporationInventor: Iwao Takagishi
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Patent number: 5182382Abstract: 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: GrantFiled: May 28, 1991Date of Patent: January 26, 1993Assignee: Xerox CorporationInventors: James D. Mayo, James M. Duff, Terry L. Bluhm, Cheng K. Hsiao
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Patent number: 5164493Abstract: A process for the preparation of titanyl phthalocyanine which comprises the reaction in a solvent of phthalonitrile and diiminoisoindoline with titanium tetraalkoxide.Type: GrantFiled: February 28, 1991Date of Patent: November 17, 1992Assignee: Xerox CorporationInventors: James D. Mayo, James M. Duff