From Reactant Which Contains Plural Carbonyl Groups (e.g., Preparing From Phthalic Anhydride, Etc.) Patents (Class 540/144)
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Patent number: 9108247Abstract: A nanopowder and a method of making are disclosed. The nanopowder may be in the form of nanoparticles with an average size of less than about 200 nm and contain a reactive transition metal, such as hafnium, zirconium, or titanium. The nanopowder can be formed in a liquid under sonication by reducing a halide of the transition metal.Type: GrantFiled: May 16, 2014Date of Patent: August 18, 2015Assignee: The United States of America, as represented by the Secretary of the NavyInventors: Albert Epshteyn, Andrew P. Purdy
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Patent number: 9056810Abstract: The present invention disclosed a preparation method of parylene AF4, which provides a reactant and a reducing agent with the use of catalyst or exposure to UV light with photo-initiator, to shorten the reaction time as a result of minimized the byproduct(s) formation, and obtain high purity (>99.0%) of parylene AF4 product under high concentrated reaction mixture.Type: GrantFiled: April 7, 2014Date of Patent: June 16, 2015Assignee: YUAN-SHIN MATERIALS TECHNOLOGY CORP.Inventors: Chun-Hsu Lin, Chien-Yi Sun, Yung-Yu Yin, Chun-Shih Li, Yo-Chun Chou
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Patent number: 8318005Abstract: 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: GrantFiled: December 21, 2007Date of Patent: November 27, 2012Assignee: DOW Global Technologies LLCInventors: John M. Griffin, Stephen A. Bedell, Clare M. Worley
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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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Publication number: 20090036670Abstract: A method of preparing a naphthalocyanine is provided. The method comprises the steps of: (i) providing a tetrahydronaphthalic anhydride; (ii) converting said tetrahydronaphthalic anhydride to a benzisoindolenine; and (iii) macrocyclizing said benzisoindolenine to form a naphthalocyanine.Type: ApplicationFiled: August 1, 2007Publication date: February 5, 2009Inventors: Sutharsiny Indusegaram, Simone Charlotte Vonwiller, Damon Donald Ridley, Kia Siverbrook
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Publication number: 20090036671Abstract: A method of effecting a one-pot conversion of a tetrahydronaphthalic anhydride to a benzisoindolenine salt is provided. The method comprises heating the tetrahydronaphthalic anhydride with a reagent mixture comprising ammonium nitrate.Type: ApplicationFiled: August 1, 2007Publication date: February 5, 2009Inventors: Sutharsiny Indusegaram, Simone Charlotte Vonwiller, Damon Donald Ridley, Kia Silverbrook
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Patent number: 6103896Abstract: A process for the production of a metal phthalocyanine excellent in color-related properties such as tinting strength, clearness and hue, in which no reactions of raw materials with a solvent take place and a substance harmful to human bodies such as polychlorinated biphenyl (PCB) is not formed, the process comprising heating phthalic anhydride or phthalimide, urea, metal salt and a catalyst in mixed solvents of chlorinated benzene and a linear hydrocarbon.Type: GrantFiled: April 2, 1999Date of Patent: August 15, 2000Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Atsushi Endo, Yasumasa Suda
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Patent number: 5910585Abstract: A process for the production of copper phthalocyanine, which overcomes the defect of a method using two reaction steps that since phthalimide formed in the first step adheres to the wall of a reactor and a stirring blade, the reaction in the second step does not smoothly proceed, so that the yield and the purity of the resultant pigment are low, and which process enables the industrially stable production of highly pure copper phthalocyanine at high yields,the process comprising the steps of(A) reacting phthalic anhydride or a phthalic anhydride derivative with ammonia to form phthalimide,(B) adding part or all of urea to the phthalimide obtained in step (A) and melting the mixture under heat to form a homogeneous slurry, and(C) adding copper or a copper compound and remaining urea if any to the slurry obtained in step (B) and forming a copper phthalocyanine or a copper phthalocyanine derivative in the presence of a catalyst.Type: GrantFiled: April 21, 1998Date of Patent: June 8, 1999Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Atsushi Endo, Yasumasa Suda
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Patent number: 5883245Abstract: The present invention provides a deodorizer consisting of the water-soluble metallophthalocyanine represented by the formula: ##STR1## wherein, "Met" is a central metal, X is an acidic group or alkali metal salt thereof, m and p are respectively an integer of from 1 to 15, and m+p is not more than 16. The deodorizer shows excellent deodorizing ability for an aldehyde-origin odor.Type: GrantFiled: October 2, 1997Date of Patent: March 16, 1999Assignee: Orient Chemical Industries, Ltd.Inventors: Yasuhiro Yamasaki, Tatsuto Yamashita
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Patent number: 5859237Abstract: A process for the production of a phthalocyanine pigment having a clear color tone, a high tinting strength and a finely milled structure by an efficient and economical process, in which the pigmentation from a phthalocyanine crude can be carried out without removing an aromatic hydrocarbon solvent used in the synthesis of the phthalocyanine crude, the process comprising thes steps of(a) reacting phthalic anhydride or its derivative, urea or its derivative and a catalyst in an organic solvent to synthesize a phthalocyanine crude,(b) wet-milling a slurry of the synthesized phthalocyanine crude in the presence of a milling medium without removing the aromatic hydrocarbon solvent, and(c) removing the organic solvent from the slurry of the milled product, purifying the milled product and drying the milled product with a spray type dryer.Type: GrantFiled: October 8, 1997Date of Patent: January 12, 1999Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Hideko Noguchi, Mikio Hayashi, Masatoshi Momose
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Patent number: 5834608Abstract: Copper phthalocyanine is prepared by heating and reacting phthalic acid or a derivative thereof, urea or a derivative thereof and copper or a copper compound in the presence of molybdenum or a molybdenum compound as a catalyst and sulfur.Type: GrantFiled: May 30, 1996Date of Patent: November 10, 1998Assignee: Kawasaki Kasei Chemicals Ltd.Inventor: Kazuhiro Maruyama
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Patent number: 5831083Abstract: A production method of beta-type copper phthalocyanine pigment comprising steps of: a) producing a reaction mixture containing crude copper phthalocyanine in an organic solvent; b) wet-grounding the reaction mixture by mechanical energy to form a suspension; c) removing the organic solvent from the obtained suspension does not contaminate the work environment and represents an improvement in terms of both productivity and economic savings compared with conventional methods. The beta-type copper phthalocyanine pigment produced by this method demonstrates excellent dispersability, such that it may be dispersed without further modification in a resin, varnish, plastic or other medium as required, to produce a paint, ink, or plastic tinting agent, for example.Type: GrantFiled: January 3, 1997Date of Patent: November 3, 1998Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Kouji Ohno, Akemi Kanai, Toshio Takei
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Patent number: 5800607Abstract: Process for the preparation of pigment preparations, which comprises wet milling the crude pigments which are present in coarsely crystalline state, or prepigments or pigments which are present in a form in which they are difficult to disperse, in a concentration of from 20 to 60% by weight based on the total weight of the pigment preparation, in a flocculation-stable liquid medium and in a stirred ball mill which is operated with a peripheral stirrer speed of more than 12 m/s, under the action of nonmetallic grinding media with a diameter of less than or equal to 1.0 mm, until the desired degree of fine division is reached, and then isolating the pigment preparation.Type: GrantFiled: July 3, 1996Date of Patent: September 1, 1998Assignee: Hoechst AktiengesellschaftInventors: Dieter Schnaitmann, Martin Bohmer, Manfred Urban
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Patent number: 5721358Abstract: A process for the production of a highly pure copper phthalocyanine at high yields while improving the state of a reaction system, the improvement in which a dispersing agent of the formula (1) in the form of a polymer is added to the reaction system,A--(O--R.sup.1 --CO).sub.n --B (1)wherein A is hydrogen, a linear or branched alkyl group having 1 to 20 carbon atoms, a linear or branched alkenyl group having 1 to 20 carbon atoms or a polyisobutylene residue having a polymerization degree of 50 to 500, R.sup.1 is a linear or branched aliphatic residue having up to 20 carbon atoms, n is a number in the range of 0.ltoreq.n.ltoreq.20, and when n=0, B is a compound of the formula (2), ##STR1## wherein P is (CH.sub.2 CH.sub.2 NH).sub.k CH.sub.2 CH.sub.2 NH.sub.2 in which k is an integer of 0 to 20 or an alkyleneamine group having 3 to 20 carbon atoms, or when n.noteq.0, B is a compound of the formula (3),--X--(C.sub.m --H.sub.2m)--Q (3)wherein X is --NH-- or --O--, m is a number of 0 to 6 and Q is --NR.sup.2 R.sup.Type: GrantFiled: July 10, 1996Date of Patent: February 24, 1998Assignees: Toyo Ink Manufacturing Co., Ltd., Francolor PigmentsInventors: Michichika Hikosaka, Gerard Coispeau
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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: 5602249Abstract: A process for the production of a copper phthalocyanine by a urea method, which enables the production of a highly pure copper phthalocyanine and/or its derivative by a uniform reaction, i.e., is free from problems of an insufficient mixing, nonuniformity in heat transfer and adhesion of the reaction mixture to a reactor wall, the process comprising heating a raw material mixture containing a phthalic acid, a nitrogen source, a copper compound and a catalyst in an inert solvent, the process being carried out in the presence of a surfactant which enables the raw material mixture and a reaction product to be dispersed in the inert solvent while the raw materials are being reacted and which can be removed or deactivated by hydrolysis with an acid or an alkali at a step of purifying the reaction product or forming the reaction product into a pigment after the reaction.Type: GrantFiled: March 29, 1995Date of Patent: February 11, 1997Assignee: Toyo Ink Manufacturing Co., Ltd.Inventor: Michichika Hikosaka
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Patent number: 5534055Abstract: This invention relates to a process for preparing alpha-phase metal phthalocyanine pigments from crude metal phthalocyanine pigments comprising(a) acid pasting or acid swelling a crude metal phthalocyanine pigment;(b) dry milling the acid-pasted or acid-swelled metal phthalocyanine pigment in the presence of 5 to 50 parts by weight of a stabilizer per 100 parts by weight of the crude metal phthalocyanine pigment until the average particle size is reduced to less than about 0.5 .mu.m;(c) finishing the milled metal phthalocyanine pigment by thoroughly mixing said milled metal phthalocyanine pigment with a finishing solvent mixture comprising 3 to 6 parts by weight, relative to the crude metal phthalocyanine pigment, of water and 0.4 to 1.Type: GrantFiled: August 24, 1994Date of Patent: July 9, 1996Assignee: Bayer CorporationInventors: Herman Gerson, Abdul Sattar
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Patent number: 5496939Abstract: A method for producing copper phthalocyanine, which comprises heating and reacting phthalic acid or a phthalic acid derivative, urea or a urea derivative, and a copper compound, using molybdenum or a molybdenum compound as a catalyst, in the presence or absence of an inert organic solvent, wherein at least one compound selected from the group consisting of an aromatic dithiol compound of the following formula (I), a saturated aliphatic dithiol compound of the following formula (II), and their precursors, or at least one compound selected from the group consisting of a ruthenium compound and an osmium compound, is added to the reaction system: ##STR1##C.sub.m H.sub.2m-x R.sub.x (SH).sub.2 (II)wherein ring A in the formula (I) is a 6-membered single carbon ring or polycyclic condensed carbon ring aromatic compound, R for R.sub.n in the formula (I) or for R.sub.Type: GrantFiled: March 8, 1995Date of Patent: March 5, 1996Assignee: Kawasaki Kasei Chemicals Ltd.Inventor: Kazuhiro Maruyama
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Patent number: 5492563Abstract: Copper phthalocyanine pigments are finely divided in an ecologically and economically advantageous manner by first of all subjecting crude, coarsely crystalline copper phthalocyanine pigments to dry milling and then wet milling the finely divided prepigments which are obtained in the course of dry milling, in aqueous suspension and with the addition of from 0.1 to 5% by weight, based on the total millbase, of an organic solvent which is inert with respect to the process conditions, on a stirred ball mill which is operated at an energy density of more than 2.5 kW per liter of milling space and a peripheral stirrer speed of more than 12 m/s under the action of grinding media having a diameter of less than or equal to 1 mm. Copper phthalocyanine pigments prepared in this way are particularly suitable as colorants for pigmenting paints, printing inks and plastics.Type: GrantFiled: April 13, 1995Date of Patent: February 20, 1996Assignee: Hoechst AGInventor: Manfred Urban
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Patent number: 5449774Abstract: The present invention provides a process for producing beta-form pigmentary copper phthalocyanine comprising a) producing crude copper phthalocyanine by charging phthalic anhydride or phthalimide, urea, a copper compound and a catalyst, at a substantially continuous and uniform rate, into a reaction chamber containing dry, granular, pre-formed copper phthalocyanine, and removing the reaction product from the reaction chamber; and b) convening the crude copper phthalocyanine produced in step a) into pigmentary form, by milling it either in the dry state or in an aqueous medium; mixing the milled material with an aqueous emulsion comprising i) a liquid C.sub.6 -C.sub.20 amine which is insoluble in water or alkali but is soluble in acid and ii) a surfactant capable of emulsifying the liquid amine; rendering the resulting mixture acidic to thereby dissolve the amine; and finally separating the desired pigmentary copper phthalocyanine from the treatment mixture.Type: GrantFiled: April 1, 1991Date of Patent: September 12, 1995Assignee: Ciba-Geigy CorporationInventors: Ian A. Lambie, Michael D. McFarlane, Robert Langley
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Patent number: 5393339Abstract: This invention relates to an improved process for preparing metal phthalocyanine pigments comprising(a) heating at a temperature of about 150.degree. C. to about 200.degree. C. a mixture comprising(i) a phthalocyanine-forming material based on phthalic acid,(ii) at least about 25 mole percent, relative to the phthalocyanine-forming material (i), of a metal donor,(iii) at least about 100 mole percent, relative to the phthalocyanine-forming material (i), of a nitrogen donor,(iv) 1 to about 20 percent by weight, relative to the phthalocyanine-forming material (i), of a catalyst, and(v) about 250 to about 400 percent by weight, relative to the phthalocyanine-forming material (i), of a di(C.sub.1 -C.sub.3 alkyl) phthalate solvent; and(b) isolating the metal phthalocyanine pigment.Type: GrantFiled: May 11, 1994Date of Patent: February 28, 1995Assignee: Miles Inc.Inventors: Herman Gerson, Abdul Sattar
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Patent number: 5318623Abstract: A process for producing a metal phthalocyanine pigment which comprises the steps of: reacting phthalic anhydride or a derivative thereof with urea or a derivative thereof with heating in the presence of a catalyst either in the presence or absence of an organic solvent; adding to the reaction mixture of the preceding step a metal or its compound capable of constituting the core of the metal phthalocyanine either alone or together with urea or a derivative thereof, without isolating the reaction product from the reaction mixture of the preceding step; and allowing the reaction mixture to react while simultaneously applying a mechanical grinding force in the presence or absence of a grinding agent.Type: GrantFiled: April 30, 1993Date of Patent: June 7, 1994Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Shinichi Azuma, Takashi Kano, Takanori Miyake, Hideo Shimizu
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Patent number: 5296033Abstract: Phthalocyanine pigments and phthalocyanine pigment preparations in the .alpha. phase and in the .beta. phase are prepared with phase conservation in an environmentally safe and economical manner bya) first wet milling a phthalocyanine pigment in an inert liquid medium in a stirred ball mill which is operated at a power density of more than 2.Type: GrantFiled: June 18, 1993Date of Patent: March 22, 1994Assignee: Hoechst AktiengesellschaftInventors: Erwin Dietz, Manfred Urban
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Patent number: 5296034Abstract: Copper phthalocyanine pigments and pigment preparations in the .alpha. phase are prepared with phase conversion from copper phthalocyanine crude pigments of the .beta. phase in an environmentally safe and economical manner bya) first wet milling a copper phthalocyanine pigment, which is predominantly present in the .beta. phase, in an aqueous, preferably neutral to alkaline medium in a stirred ball mill which is operated at a power density of more than 2.Type: GrantFiled: June 18, 1993Date of Patent: March 22, 1994Assignee: Hoechst AktiengesellschaftInventors: Erwin Dietz, Manfred Urban
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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: 5229508Abstract: A process for the preparation of a copper phthalocyanine pigment, which comprises dry grinding crude copper phthalocyanine, treating the dry ground crude copper phthalocyanine with an aqueous solution of a mineral acid under such conditions of acid concentration and temperature as not to transform the .beta. form contained in the ground crude copper phthalocyanine into the .alpha. one to thereby carry out the pigmentation and removing the mineral acid from the resulting mixture.Type: GrantFiled: December 13, 1991Date of Patent: July 20, 1993Assignee: Toyo Ink Manufacturing Co., Inc.Inventors: Toshimitsu Ikegaya, Yusaku Ide, Tsuneo Kawamura, Michichika Hikosaka
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Patent number: 5153314Abstract: A process for producing a copper phthalocyanine compound, which comprises heating and reacting phthalic acid or a phthalic acid derivative, urea or a urea derivative and cuprous chloride in the presence of a catalyst in an inert organic solvent, wherein the cuprous chloride is used in an amount of from 95 to 99% of the stoichiometric amount relative to the phthalic acid or the phthalic acid derivative.Type: GrantFiled: October 31, 1990Date of Patent: October 6, 1992Assignee: Kawasaki Kasei Chemicals Ltd.Inventors: Tomio Segawa, Kazuhiro Maruyama, Tadashi Ninomiya, Motokazu Suyama
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Patent number: 5138047Abstract: This invention relates to improved catalytic process for the manufacture of copper phthalocyanine by allowing phthalic anhydride to react with urea and a copper compound, in the presence of a hydrophobic liquid (dispersing agent), characterized by the presence, along with the catalyst and the dispersing agent, of a promoter selected from particular classes of amides, imides, ureas, thioureas, guanidines, amines or sulphoxides.Type: GrantFiled: December 6, 1990Date of Patent: August 11, 1992Assignee: ACNA Chimica Organica S.P.A.Inventors: Giorgio Bornengo, Giovanni Agnes, Augusto Menconi, Giorgio Bottaccio, Zafferino Bozzolasco, Danilo Domenis
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Patent number: 4906747Abstract: In a process for producing a metal phthalocyanine and/or its derivative by heating phthalic anhydride and/or its derivative, urea and a metal compound in an organic solvent in the presence of a catalyst, or by heating phthalodinitrile and a metal or a metal compound in an organic solvent, the improvement wherein the reaction for the production of the metal phthalocyanine and/or its derivative is conducted by an addition of cyanuric acid and/or its derivative.Type: GrantFiled: December 15, 1988Date of Patent: March 6, 1990Assignee: Kawasaki Kasei Chemicals Ltd.Inventors: Tomio Segawa, Kazuhiro Maruyama, Tadashi Ninomiya, Motokazu Suyama
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Patent number: 4801702Abstract: A process for the preparation and conditioning of organic pigments, which comprises the use of at least one tricyclodecane alcohol or tricyclodecene alcohol.Type: GrantFiled: October 30, 1986Date of Patent: January 31, 1989Assignee: Ciba-Geigy CorporationInventor: Fridolin Babler
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Patent number: 4785091Abstract: Copper phthalocyanine pigment which is a coloring material for ink or paint is prepared by allowing, for example, phthalate, urea, and cuprous chloride to react in a hydrophilic solvent in the presence of a catalyst and at least one element selected from the group consisting of aliphatic tetracarboxylic acids, benzophenone 3,3',4,4'-tetracarboxylic acid or anhydride thereof, pyromellitic acid or anhydride thereof, copper phthalocyanine sulfonic acids, copper phthalocyanine carbonyl imide, tetrahydrophthalic acid or derivative thereof, pyromellitic imide or derivative thereof, sulfophthalic acid, derivative thereof or the salt thereof and benzene carboxylic acid.Type: GrantFiled: October 20, 1987Date of Patent: November 15, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Taira Fujita, Toshiaki Kishimoto, Hiroshi Okayasu