Metal Containing Patents (Class 540/139)
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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: 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: 5484915Abstract: A substituted phthalocyanine in which at least one of the peripheral carbon atoms in the 1-16 positions of the phthalocyanine nucleus (MnPc) as shown in Formula (1) ##STR1## is linked via an oxygen atom or a sulphur atom to an organic radical, the remaining peripheral carbon atoms being unsubstituted or substituted by any combination of atoms or groups and sulphonated derivatives thereof. Compositions comprising one or more compounds of Formula (1) and their use as cleaning materials are also disclosed along with a process for removing stains and/or grime from fabrics using these compositions.Type: GrantFiled: July 6, 1994Date of Patent: January 16, 1996Assignee: Zeneca LimitedInventors: Peter Gregory, Stephen J. Reynolds, Raymond L. White
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Patent number: 5484685Abstract: A naphthalocyanine derivative of the formula: ##STR1## wherein M, Y, R.sup.1, k, l, m, n are as defined in the specification, is an effective substance for forming a recording layer on a substrate of an optical recording medium having high sensitivity with good properties.Type: GrantFiled: May 30, 1991Date of Patent: January 16, 1996Assignees: Hitachi, Ltd., Hitachi Chemical Co., Ltd.Inventors: Seiji Tai, Nobuyuki Hayashi, Koichi Kamijima, Mitsuo Katayose, Takayuki Akimoto, Shigeru Hayashida, Hideo Hagiwara, Susumu Era, Setsuo Kobayashi, Akio Mukoh
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Patent number: 5466796Abstract: Alkoxy-bridged metallophthalocyanine dimers of the formula C.sub.32 H.sub.16 N.sub.8 MOROMN.sub.8 H.sub.16 C.sub.32, or of the formula ##STR1## wherein M is a metal, and R is an alkyl or an alkyl ether.Type: GrantFiled: April 26, 1994Date of Patent: November 14, 1995Assignee: 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: 5463041Abstract: A process for preparing a purified hydroxymetal phthalocyanine with stable charging characteristics and small dark decay and an electrophotographic photoreceptor containing the same are disclosed. The process comprises dissolving or slurrying a precursor of a hydroxymetal phthalocyanine in an acid, precipitating a hydroxymetal phthalocyanine in a solvent or a basic solution, and heat treating the resulting hydroxymetal phthalocyanine in a basic solution. The purified hydroxymetal phthalocyanine wherein the metal is gallium is further subjected to a solvent treatment to provide a new crystal showing further improved electrophotographic characteristics.Type: GrantFiled: June 14, 1993Date of Patent: October 31, 1995Assignee: Fuji Xerox Co., Ltd.Inventors: Katsumi Nukada, Katsumi Daimon
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Patent number: 5463042Abstract: A layered double hydroxide intercalated with a metal complex of a polyaryl compound is described. A preferred complex is porphin or phthylocyanine. The metals are preferably selected from Group VII-B and Group VIII cobalt and iron triads. The resulting LDH metal complexes are useful for the oxidation of oxidate compounds such as thiols and phenols.Type: GrantFiled: January 25, 1994Date of Patent: October 31, 1995Assignee: Board of Trustees operating Michigan State UniversityInventors: Thomas J. Pinnavaia, Elena M. Perez-Bernal, Ricardo Ruarno-Casero, Malama Chibwe
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Patent number: 5463043Abstract: A novel dichlorotin phthalocyanine crystal having distinct diffraction peaks at 8.5.degree., 11.2.degree., 14.5.degree., and 27.2.degree. of the Bragg angles (2.theta..+-.0.2) in the X-ray diffraction spectrum; a process for producing the dichlorotin phthalocyanine crystal, comprising mechanically grinding a known dichlorotin phthalocyanine crystal together with an inorganic salt, followed by, if desired, a solvent treatment; an electrophotographic photoreceptor containing, in the photosensitive layer thereof, the dichlorotin phthalocyanine crystal; and a coating composition for producing an electrophotographic photoreceptor, comprising the dichlorotin phthalocyanine crystal, a binder resin, and an acetic ester solvent. The photoreceptor exhibits high sensitivity and excellent durability. The coating composition maintains the dichlorotin phthalocyanine crystal in its desired form either while being prepared or after being coated.Type: GrantFiled: May 10, 1994Date of Patent: October 31, 1995Assignee: Fuji Xerox Co., Ltd.Inventors: Katsumi Nukada, Akira Imai, Katsumi Daimon, Masakazu Iijima, Kiyokazu Mashimo, Yasuo Sakaguchi, Ichiro Takegawa
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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: 5459259Abstract: A layered double hydroxide intercalated with a metal complex of a polyaryl compound is described. A preferred complex is porphin or phthylocyanine. The metals are preferably selected from Group VII-B and Group VIII cobalt and iron triads. The resulting LDH metal complexes are useful for the oxidation of oxidate compounds such as thiols and phenols.Type: GrantFiled: January 25, 1994Date of Patent: October 17, 1995Assignee: Board of Trustees operating Michigan State UniversityInventors: Thomas J. Pinnavaia, Elena M. Perez-Bernal, Ricardo Ruarno-Casero, Malama Chibwe
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Patent number: 5446142Abstract: The present invention provides a light-absorbing compound represented by the formula (I):Dye-(OR.sup.1)(OR.sup.2)(OR.sup.3) . . . (OR.sup.n) (I)wherein Dye is a light-absorbing compound residue having at least one aromatic ring; OR.sup.1 to OR.sup.n are substituents on the aromatic ring, and are independently (a) substituted or unsubstituted saturated hydrocarbonoxy groups having 1 to 20 carbon atoms, or (b) substituted or unsubstituted unsaturated hydrocarbonoxy groups having 2 to 20 carbon atoms, and at least one of OR.sup.1 to OR.sup.n is an unsaturated hydrocarbonoxy group; and n is a value of from 1 to 10. The present invention also provides an optical recording medium containing the above-mentioned light-absorbing compound in a recording layer.Type: GrantFiled: June 11, 1993Date of Patent: August 29, 1995Assignees: Mitsui Toatsu Chemicals, Inc., Yamamoto Chemicals, Inc.Inventors: Hisato Itoh, Takahisa Oguchi, Kenichi Sugimoto, Ryu Oi, Hideki Umehara, Shin Aihara
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Patent number: 5446141Abstract: Near-infrared absorbers which contain phthalocyanine derivatives in which the four benzene rings contained in the molecule independently have 1 to 4 substituents are light and thermal resistant and possess high molar extinction coefficients. Such near-infrared absorbers are useful in optical recording media, near-infrared absorption filters, and liquid crystal display devices.Type: GrantFiled: September 17, 1992Date of Patent: August 29, 1995Assignees: Mitsui Toatsu Chemicals, Incorporated, Yamamoto Chemicals, IncorporatedInventors: Hisato Itoh, Katashi Enomoto, Takahisa Oguchi, Tsutomu Nishizawa
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Patent number: 5437929Abstract: A process for preparing film structures comprising phthalocyanine oligomers having metal coordinating atoms in adjacent rings connected along a central axis through oxygen atoms. The ligands on the outermost rings of the structures are hydrophilic. The preferred coordinating atom is germanium and the structures may be prepared on a Langmuir-Blodgett balance using phthalocyanine oligomers in which one of the outermost rings is connected to a hydrophobic ligand while the other outermost ring is connected to a hydrophilic ligand. The pH of the subphase in the trough of the balance is maintained at a pH of from about 2 to 6, and the hydrophobic ligand is converted to a hydrophilic ligand during the process of coating a substrate by passing it upward through the film on the subphase.Type: GrantFiled: January 19, 1994Date of Patent: August 1, 1995Assignee: Edison Polymer Innovation Corp.Inventors: Malcom E. Kenney, Terri R. Clark
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Patent number: 5427616Abstract: A process for the production of a copper phthalocyanine pigment composition from 70 to 99% by weight of a crude copper phthalocyanine and 30 to 1% by weight of a phthalocyanine derivative,the crude copper phthalocyanine being converted to a pigment without a large amount of energy and the treatment of exhaust water,the copper phthalocyanine pigment composition having excellent fluidity, tinting strength and stability with time when used in a coating composition or a printing ink,the copper phthalocyanine pigment composition showing almost no "strike-through" when used for gravure printing on low-quality paper,the process comprising dry milling the entirety of the crude copper phthalocyanine and the phthalocyanine derivative in an amount of 0.5 to 10% by weight of a final composition in the absence of a milling auxiliary until the content of an .alpha.Type: GrantFiled: June 1, 1994Date of Patent: June 27, 1995Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Kosaku Tsuji, Yoshio Muramatsu, Shigeki Kato
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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: 5393881Abstract: A halogenated hydroxygallium phthalocyanine crystal shows intense diffraction peaks at Bragg angles (2.THETA..+-.0.2.degree.) of (1) 7.7.degree., 16.5.degree., 25.1.degree. and 26.6.degree.; (2) 7.9.degree., 16.5.degree., 24.4.degree., and 27.6.degree.; (3) 7.0.degree., 7.5.degree., 10.5.degree., 11.7.degree., 12.7.degree., 17.3.degree., 18.1.degree., 24.5.degree., 26.2.degree., and 27.1.degree.; (4) 7.5.degree., 9.9.degree., 12.5.degree., 16,3.degree., 18.6.degree., 25.1.degree., and 28.3.degree. or (5) 6.8.degree., 12.8.degree., 15.8.degree., and 26.0.degree. and is suited for use in an electrophotographic photoreceptor is disclosed.Type: GrantFiled: August 19, 1993Date of Patent: February 28, 1995Assignee: Fuji Xerox Co., Ltd.Inventors: Katsumi Nukada, Katsumi Daimon
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Patent number: 5380842Abstract: Phthalocyanine compounds represented by the below-described formula are suitable for use in the fabrication of color filters. ##STR1## wherein R.sup.1, R.sup.4, R.sup.5, R.sup.8, R.sup.9, R.sup.12, R.sup.13 and R.sup.16 represent a group represented by the below-described formula, H or a halogen atom, R.sup.2, R.sup.3, R.sup.6, R.sup.7, R.sup.10, R.sup.11, R.sup.14 and R.sup.15 represent an alkyl, alkoxyl, alkylthio, alkylamino, dialkylamino or aryloxyl, arylthio group or --COOR.sup.17, R.sup.17 being a particular monovalent group, H or a halogen atom; and Met represents a metal atom. ##STR2## wherein X and Z represent O or S, R.sup.18, R.sup.19 and R.sup.20 represent H or an alkyl group, A, B and D represent a connecting group, n and l is an integer of 0-10, m, q, t, u, r and w are an integer of 0-2, and p is 0 or 1.Type: GrantFiled: June 22, 1992Date of Patent: January 10, 1995Assignees: Mitsui Toatsu Chemicals, Incorporated, Yamamoto Chemicals, IncorporatedInventors: Hisato Itoh, Akio Karasawa, Kenichi Sugimoto, Takahisa Oguchi, Shin Aihara
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Patent number: 5360475Abstract: A process for preparing a hydroxymetal phthalocyanine pigment containing a central metal atom selected from aluminum, gallium, indium, silicon, germanium and tin and having a novel crystal form is disclosed, comprising treating a precursor of a hydroxymetal phthalocyanine pigment with an acid and treating the precipitated hydroxymetal phthalocyanine pigment with a solvent under an acidic condition. The resulting hydroxymetal phthalocyanine pigment includes hydroxygallium crystals showing distinct diffraction peaks at Bragg angles (2.theta..+-.0.2.degree.) of (1) 8.2.degree., 12.4.degree., 16.5.degree. and 26.3.degree. or (2) 6.8.degree., 12.5.degree. and 26.4.degree.. The resulting hydroxymetal phthalocyanine pigment exhibits high photosensitivity and excellent stability as a charge generating material of an electrophotographic photoreceptor.Type: GrantFiled: October 5, 1993Date of Patent: November 1, 1994Assignee: Fuji Xerox Co., Ltd.Inventors: Katsumi Nukada, Katsumi Daimon, Yasuo Sakaguchi
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Patent number: 5348840Abstract: An optical recording medium which has physical and chemical stability, has high sensitivity to laser light and permits accurate recording and highly reliable reproduction. The medium comprises a transparent substrate and a recording layer formed on the substrate, the recording layer being formed of an organic thin layer containing at least one of phthalocyanine compounds of the formula [1].Type: GrantFiled: May 5, 1993Date of Patent: September 20, 1994Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Makoto Sakamoto, Michiko Tamano
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Patent number: 5346670Abstract: Red-shifted, water-soluble, fluorescent, monomerically-tetherable derivatives having the formula: ##STR1##wherein, M represents either H.sub.2 or is selected from among the following metals: aluminum, silicon, phosphorus, gallium, germanium, cadmium, scandium, magnesium, tin, and zinc. Each R.sub.1 is independently selected from --XYW, --YW, and --W. X represents either a carbon, or heteroatom selected from among oxygen, nitrogen, sulfur, phosphorus, silicon, and selenium; Y represents a linking group; and W represents a water solubilizing group. The substituent R.sub.2 is selected from among --A, --Y'A, --XA, and --XY'A, where A denotes a biological entity such as an antibody, antibody fragment, nucleotide, nucleic acid probe, antigen, oligonucleotide, deoxynucleotide, dideoxynucleotide, avidin, streptavidin or membrane probe, or R.sub.2 is a reactive or activatable group suitable for conjugating to a biological entity.Type: GrantFiled: June 8, 1992Date of Patent: September 13, 1994Assignee: British Technology Group U.S.A. Inc.Inventors: George E. Renzoni, Deborah C. Schindele, Louis J. Theodore, Clifford C. Leznoff, Karen L. Fearon, Barry V. Pepich
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Patent number: 5345032Abstract: A method for dehalogenation of organohalogen compounds, e.g. environmental pollutants in industrial waste. The organohalogen is reacted with a reducing agent in the presence of a selected metal-centered corrin, porphyrin or phthalocyanine complex. Preferred complexes are hydrolysis products of cyanocobalamin, of formula (I), in which R.sup.1 is NH.sub.2 or OH, R.sup.2 is H, CH.sub.2 CH.sub.2 COOH or CH.sub.2 CH.sub.2 CONH.sub.2, R.sup.3 is H, CH.sub.2 CH.sub.2 COOH or CH.sub.2 CH.sub.2 CONH.sub.2, and R.sup.4 is NHCH.sub.2 CH(OH)CH.sub.3, OH or NH.sub.2. The complex is preferably immobilized on a substrate. Some novel metal-centered porphyrin complexes are also described. A dehalogenation apparatus using the method of the invention is also described.Type: GrantFiled: April 19, 1993Date of Patent: September 6, 1994Assignee: The Public Health Laboratory Service BoardInventors: Trevor S. Marks, Andrew Maule
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Patent number: 5322760Abstract: A nonlinear optical element comprising a tetraazaporphyrin compound represented by the formula (I): ##STR1## This nonlinear optical element is excellent in that it is improved over low switching speed of the conventional inorganic materials and over small nonlinearity and poor chemical and physical stability and workability of the conventional organic materials.Type: GrantFiled: November 29, 1991Date of Patent: June 21, 1994Assignee: Hitachi, Ltd.Inventors: Yuzo Itoh, Atsushi Kakuta, Akio Mukoh
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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: 5319074Abstract: A metal-free dyestuff of the formula ##STR1## and metal complex thereof wherein: Fb=the radical of a dyestuff selected from the group consisting of mono- or polyazo, anthraquinone, phthalocyanine, formazan, dioxazine and triphenylmethane radicals,B and B'=a direct bond or an aliphatic or aromatic bridge member to a ring C atom of an aromatic-carbocyclic ring or to a ring C or N atom or an aromatic-heterocyclic ring in Fb,X=CH.dbd.CH.sub.2 or CH.sub.2 CH.sub.2 --Y, whereinY=OSO.sub.3 H, SSO.sub.3 H, OCOCH.sub.3, OPO.sub.3 H.sub.2, OSO.sub.2 CH.sub.3, SCN, NHSO.sub.2 CH.sub.3 --, Cl, Br, F, OCOC.sub.6 H.sub.5, OSO.sub.2 --C.sub.6 H.sub.4 CH.sub.3, ##STR2## R=H or C.sub.1 -C.sub.4 -alkyl, which is optionally be substituted by halogen, hydroxy, cyano, C.sub.1 -C.sub.4 -alkoxy, carboxyl, sulpho or sulphato,Z=a fiber-reactive radical of the formula ##STR3## wherein M=H, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -thioalkyl, F or CF.sub.Type: GrantFiled: January 24, 1992Date of Patent: June 7, 1994Assignee: Bayer AktiengesellschaftInventors: Wolfram Reddig, Karl-Josef Herd, Ernst Kysela
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Patent number: 5298607Abstract: The invention provides reactive dyes of the formula ##STR1## wherein D is a mono- or polyazo, metal complex azo, anthraquinone, phthalocyanine, formazane, dioxazine or stilbene dye which contains sulfo groups, R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.2 is hydrogen, methyl or ethyl, X is a radical of the formula --SO.sub.2 CH.sub.2 CH.sub.2 Cl, --SO.sub.2 CH.dbd.CH.sub.2, --SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H, --SO.sub.2 CH.sub.2 CH.sub.2 OPO.sub.3 H or --N(R.sub.3)SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H, and R.sub.3 is hydrogen, methyl or ethyl, and the benzene or naphthalene radical is not further substituted or is further substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.Type: GrantFiled: May 26, 1993Date of Patent: March 29, 1994Assignee: Ciba-Geigy CorporationInventor: Herbert Seiler
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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: 5282896Abstract: A process for producing a pigment composition containing a highly halogenated copper phthalocyanine, produced by halogenation of copper phthalocyanine in the presence of chlorosulfonic acid, titanium tetrachloride or a mixture of titanium tetrachloride with aluminum chloride, a highly halogenated copper phthalocyanine produced by halogenation of a copper phthalocyanine in a solid powder state, or a highly halogenated copper phthalocyanine produced by cyclization. The composition further contains at least one highly halogenated different-metalo-phthalocyanine selected from highly halogenated metalo-phthalocyanines each of which has Al, Mg, Si, Ti, V, Mn, Fe, Co, Ni, Zn, Ge or Sn as a central metal.Type: GrantFiled: August 16, 1991Date of Patent: February 1, 1994Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Junichi Tsuchida, Masami Shirao, Michichika Hikosaka, Yoshiyuki Nonaka
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Patent number: 5281616Abstract: Compositions for the inhibition of replication of human immunodeficiency virus containing one or more "porphyrins" possessing antiviral activity. As used herein "porphyrins" includes porphyrins, phthalocyanines, chlorins, metallo derivatives thereof, and other porphyrin-like compounds. Examples of natural and synthetic, positively, negatively, and neutrally charged porphyrins, phthalocyanines, and derivatives thereof have been found to exhibit selective anti-HIV activity which is not dependent on the presence of light.Type: GrantFiled: April 24, 1992Date of Patent: January 25, 1994Assignees: Georgia State University Foundation, Inc., Emory UniversityInventors: Dabney W. Dixon, Raymond F. Schinazi, Luigi G. Marzilli
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Patent number: 5258313Abstract: The present invention relates to a process for the detection or determination of molecular oxygen by EPR spectrometry using radical lithium phthalocyanines and a composition usable for in vivo determination. In the process, a medium is contacted with a radical lithium phthalocyanine in accordance with the formula: ##STR1## in which R.sup.2, R.sup.3, R.sup.6, R.sup.7, R.sup.10, R.sup.11, R.sup.14 and R.sup.15 represent an alkyl or an alkoxy radical group with 1-3 carbon atoms and R.sup.1, R.sup.4, R.sup.5, R.sup.8, R.sup.9, R.sup.12, R.sup.13 and R.sup.16 represent a hydrogen or deuterium atom, and the EPR signal of the radical lithium phthalocyanine in contact with the medium is examined.Type: GrantFiled: June 28, 1991Date of Patent: November 2, 1993Assignee: Commissariat a l'Energie AtomiqueInventor: Mehdi Moussavi
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Patent number: 5248336Abstract: This invention relates to solid solutions containing (a) about 90 to about 10% by weight of a chlorinated copper phthalocyanine containing about 14 to about 16 atoms of chlorine per molecule and (b) about 10 to about 90% by weight of a copper phthalocyanine containing about 3 to about 4 atoms of chlorine wherein said compositions are characterized by X-ray diffraction patterns that differ from the sum of the X-ray diffraction patterns of the individual components.Type: GrantFiled: November 5, 1991Date of Patent: September 28, 1993Assignee: Miles Inc.Inventors: Herman Gerson, Abdul Sattar
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Patent number: 5223027Abstract: A polyhalogenated phthalocyanine obtained by halogenation of phthalocyanine in the presence of aluminum chloride and contains not more than 0.02 part by weight, per 100 parts by weight of the phthalocyanine before the halogenation, of water-insoluble inorganic impurities derived from the aluminum chloride contributes to improvement of a printing ink in form plate abrasion properties.Type: GrantFiled: October 8, 1991Date of Patent: June 29, 1993Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Yoshiyuki Nonaka, Junichi Tsuchida, Masami Shirao, Michichika Hikosaka
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Patent number: 5219706Abstract: There are disclosed a novel naphthalocyanine derivative represented by the general formula [I] or [II] shown below, a process for preparing said derivative, an optical information recording medium using said derivative, and a process for preparing thereof: ##STR1## wherein M is a metal, metal oxide, metal hydroxide and the like, R.sup.1 is an alkyl group of 1-22 carbon atoms, n is an integer of 1 to 4, and Y.sub.1 and Y.sub.2 aryloxy group and the like.Type: GrantFiled: January 21, 1992Date of Patent: June 15, 1993Assignee: Hitachi, Ltd.Inventors: Seiji Tai, Shigeru Hayashida, Nobuyuki Hayashi, Yasushi Iwakabe, Shunichi Numata, Noriyuki Kinjo, Susumu Era, Setsuo Kobayashi, Akio Mukoh, Yoshio Sato
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Patent number: 5189153Abstract: A phthalocyanine compound of the Formula (1): ##STR1## wherein: Pc is a phthalocyanine nucleus which is metal free or contains a metal or oxymetal;X is S; NT or O;Y is S; NT or O;Z is S or Se; in which T in the above is H; alkyl or aryl;.sup.+ HA is an aliphatic polyamino ammonium ion or a substituted diguanidinium ion;each R independently is an aromatic radical linked to a peripheral carbon atom of the Pc nucleus through an atom Z;each R.sup.1 independently is optionally substituted phenylene or naphthylene in which the atoms X and Y are attached to adjacent nuclear carbon atoms in R.sup.1 and to adjacent peripheral carbon atoms of the Pc nucleus;a is 0 to 16; provided thatb is 0 to 8; a+b>0; andc+d is 1 to 16.Type: GrantFiled: June 19, 1990Date of Patent: February 23, 1993Assignee: Imperial Chemical Industries, PLCInventors: Peter Gregory, Prakash Patel
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Patent number: 5135717Abstract: Red-shifted, water-soluble, fluorescent, monomerically-tetherable derivatives having the formula: ##STR1## wherein, M represents either H.sub.2 or is selected from among the following metals: aluminum, silicon, phosphorus, gallium, germanium, cadmium, scandium, magnesium, tin, and zinc. Each R.sub.1 is independently selected from --XYW, --YW, and --W. X represents either a carbon, or heteroatom selected from among oxygen, nitrogen, sulfur, phosphorus, silicon, and selenium; Y represents a linking group; and W represents a water solubilizing group. The substituent R.sub.2 is selected from among --A, --Y'A, --XA, and --XY'A, where A denotes a biological entity such as an antibody, antibody fragment, nucleotide, nucleic acid probe, antigen, oligonucleotide, deoxynucleotide, dideoxynucleotide, avidin, streptavidin or membrane probe, or R.sub.2 is a reactive or activatable group suitable for conjugating to a biological entity.Type: GrantFiled: August 29, 1989Date of Patent: August 4, 1992Assignee: British Technology Group USA Inc.Inventors: George E. Renzoni, Deborah C. Schindele, Louis J. Theodore, Clifford C. Leznoff, Karen L. Fearon, Barry V. Pepich
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Patent number: 5112597Abstract: The invention relates to novel radical lithium phthalocyanine crystals, their preparation process and their use for in vivo determination of molecular oxygen.These radical lithium phthalocyanine crystals comply with the formula: ##STR1## in which R.sup.1 and R.sup.2, which can be the same or different, represent a deuterium or hydrogen atom having a tetragonal crystalline structure belonging to the space group P4/mcc.They are usable for in vivo oxygen determination by EPR spectrometry.Type: GrantFiled: June 28, 1991Date of Patent: May 12, 1992Assignee: Commissariat a l'Energie AtomiqueInventor: Mehdi Moussavi
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Patent number: 5110916Abstract: The present invention discloses lanthanide series bisphthalocyanine complex compounds, wherein chemically and thermally stable side chains effective for the development of a functional film due to generation of solubility and liquid crystallization in a solvent.The compounds according to the present invention having no reacting positions at side chains thereof possess electrochromic properties and further possess excellent electrochemical characteristics. Moreover, these compounds are soluble in a solvent and show discotic liquid crystal phase. Therefore, these compounds are very effective for the development of a functional film.Type: GrantFiled: December 21, 1990Date of Patent: May 5, 1992Assignees: Eastern Co., Ltd., Iwawo YamamotoInventors: Iwao Yamamoto, Kazuchika Ohta, Tsuyoshi Komatsu
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Patent number: 5087390Abstract: In one embodiment this invention provides a tetraazaporphyrin dye mixture which exhibits light absorption over a spectrum range of about 660-850 nm, and provides a process for production of the dye mixture.An invention dye mixture has utility in optical recording media, or as a nonlinear optical component in optical light switch or light modulator devices.Illustrative of an invention dye mixture is a blend of dye constituents respectively having varying combinations of phthalocyanine and naphthalocyanine entities in the macrocyclic structures.Type: GrantFiled: April 4, 1989Date of Patent: February 11, 1992Assignee: Hoechst Celanese Corp.Inventors: James R. Sounik, Jacquelyn Popolo
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Patent number: 5073295Abstract: There are disclosed coated active substances and a process for the preparation thereof, wherein said active substances are dyes, fluorescent whitening agents, photoactivators and/or textile microbicides, if appropriate together with extenders, dispersants, buffers, stabilizers and/or other auxiliaries.Type: GrantFiled: July 3, 1990Date of Patent: December 17, 1991Assignee: Ciba-Geigy CorporationInventors: Beat Bruttel, Petr Kvita
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Patent number: 5059510Abstract: Provided is an information recording medium, e.g., an optical recording medium, and a method for recording information thereon. The information layer of the recording medium comprises an organo macrocyclic chromophore containing a central hetero atom or two central hydrogen atoms or isotopes of hydrogen, e.g., a naphthalocyanine having silicon as the hetero atom, which chromophore is substituted with at least one substituent conferring film forming properties to the chromophore, e.g., a monomer or oligomeric substituent comprised of acid, amide or ester units. The information layer thereby offers excellent thermomechanical properties and exhibits excellent absorption properties all in a single component material. By utilizing a single component material, the problem of dye/polymer phase separation frequently encountered in dye/polymer mixtures is also overcome.Type: GrantFiled: August 22, 1989Date of Patent: October 22, 1991Assignee: Hoechst Celanese Corp.Inventors: R. Sidney Jones, Jr., David E. Nikles, Malcolm E. Kenney
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Patent number: 5039798Abstract: Provided are novel naphthalocyanine dimer compounds of the general formula:RO--YNc--O--NcY--OR (I)wherein Nc represents a naphthalocyanine moiety, which can be substituted or unsubstituted; Y represents a central hetero atom of the naphthalocyanine moiety; and, OR represents an alkoxide cap bonded to the central hetero atom Y, with the first carbon atom of the alkoxide (OR) capping group being a tertiary carbon. Also provided is a method for preparing the dimer compounds, which method comprises reacting a naphthalocyanine dihalide in solution with a tertiary alcohol and a nucleophile. The process efficiently and reproducibly provides a naphthalocyanine oxo-bridged dimer having terminal alkoxide caps.Type: GrantFiled: March 1, 1990Date of Patent: August 13, 1991Assignee: Hoechst Celanese Corp.Inventor: Robert E. Johnson
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Patent number: 5030244Abstract: Process for the preparation of granules by spray-drying of an aqueous suspension having a solids content of greater than/equal to 30% and containing at least one dye, fluorescent brightener or photoactivator and one condensation product from naphthalenesulfonic acid and formaldehyde and, if necessary, further auxiliaries and/or diluents. The spray-drying is carried out at a feed pressure of 50-150 bar, the residual moisture content of the product is less than 4%, and the granules obtained are in particular very pressure resistant and abrasion resistant.Type: GrantFiled: June 2, 1989Date of Patent: July 9, 1991Assignee: Ciba-Geigy CorporationInventors: Konrad Neumann, Angelika Hayer, Wolfgang Rehmann, Horst O. Brucker
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Patent number: 5009986Abstract: A novel naphthalocyanine based compound having Si atom as a central metal and groups selected from ##STR1## CN, and --CH.dbd.CH.sub.2 which is bonded to said Si atom via a specific hydrocarbon group, by which solubility in an organic solvent, compatibility with a polymeric substance and durability against an infrared ray are improved. The compound may be incorporated into a polymeric substance layer to form a recording layer of an optical recording medium.Type: GrantFiled: January 17, 1990Date of Patent: April 23, 1991Assignee: Teijin LimitedInventors: Takayuki Kawaguchi, Takashi Shiro, Kaoru Iwata, Takahiro Daido
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Patent number: 4996311Abstract: The invention concerns an octasubstituted lithium phthalocyanine responding to the formula: ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8, which are identical or different, represent an alkyl or alcoxy radical, possibly substituted by fluorine, and M represents Li or Li.sub.2.When M represents Li, this involves a lithium phthalocyanine octasubstituted like a radical which can be used in electronic paramagnetic resonance magnetometry.In this case, the substituents are preferably all identical and represent the methyl or methoxy radical.Type: GrantFiled: July 14, 1989Date of Patent: February 26, 1991Assignee: Commissariat a. l'Energie AtomiqueInventors: Mehdi Moussavi, Liliane Secourgeon
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Patent number: 4970021Abstract: Phthalocyanine compounds are described, which are represented by the following general formula (I): ##STR1## wherein R.sub.1 -R.sub.8 are individually a hydrogen atom or an alkyl or aryl group, a-h stand individually for an integer of 1-20, and M denotes two hydrogen atoms or a metal atom, metal halide, metal oxide, metal hydroxide, dialkylmetal, diarylmetal, bis(alkyloxy)metal or bis(trialkylsilyloxy)metal. Optical recording media and liquid crystal display panels, which contain at least one of the phthalocyanine compounds, are also described.Type: GrantFiled: August 29, 1988Date of Patent: November 13, 1990Assignees: Mitsui Toatsu Chemicals, Incorporated, Yamamoto Chemicals, IncorporatedInventors: Masakatsu Nakatsuka, Tsutomu Nishizawa, Takahisa Oguchi, Hisato Itoh, Katashi Enomoto
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Patent number: 4960538Abstract: Disclosed are near-infrared absorbents comprising 1,2-naphthalocyanine derivatives wherein the four naphthalene rings contained in the molecule independently have 1 to 6 substituents. Also disclosed is the use of these near-infrared absorbents in optical recording media, near-infrared absorption filters and display materials.Type: GrantFiled: October 20, 1988Date of Patent: October 2, 1990Assignees: Mitsui Toatsu Chemicals, Inc, Yamamoto Chemicals, Inc.Inventors: Hisato Itoh, Takahisa Oguchi, Katashi Enomoto, Masakatsu Nakatsuka, Tsutomu Nishizawa
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Patent number: 4935501Abstract: Reactive dyes of the formula ##STR1## in which D is the radical of a dye of the monoazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide series, R.sub.1 is hydrogen or an unsubstituted or substituted C.sub.1-4 -alkyl radical, and X is the vinyl, .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-chloroethyl or .beta.-acetoxyethyl group, are suitable in particular for dyeing and printing cellulose-containing fibre materials by the cold pad-batch method and produce, in high dyeing yields, dyeings and prints having good fastness properties.Type: GrantFiled: March 7, 1988Date of Patent: June 19, 1990Assignee: Ciba-Geigy CorporationInventor: Athanassios Tzikas
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Patent number: 4900817Abstract: Compounds are disclosed which comprise parallel, multiring, porphyrin-related compounds, particularly two-ring phthalocyanine compounds, which have a coordinating atom, either a metal or a metalloid, located at their center. The coordinating atoms in adjacent rings are connected by an oxygen bridge along an axial backbone disposed at right angles to the rings, and the coordinating atom and the ring on one end of the axis has a hydrophilic group attached thereto, while the coordinating atom in the ring at the other end of the axis has a hydrophobic group attached to it. Semiconducting films made from such compounds and devices made from such films, especially gas sensors, are also disclosed.Type: GrantFiled: May 31, 1988Date of Patent: February 13, 1990Assignee: Edison Polymer Innovation CorporationInventors: Daniel A. Batzel, Scott E. Rickert, Malcolm E. Kenney
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Patent number: 4814256Abstract: An optical recording material possesses a light-absorbing layer on a base, the said layer containing one or more colorants of the formula (I) ##STR1## where M is two hydrogen atoms or Fe, Cu, Co, Ni, Pb, Cr, Mn, VO, TiO, ZrO, Nb, Ta, Pd, SiCl.sub.2, Sn or SnX.sub.2, X is Cl, Br or I, and A is a divalent radical of an unsaturated, unsubstituted or substituted carbocyclic ring system.The colorants (I) present on the novel recording materials have a high absorption in the range from 650 to 850 nm and accordingly can be written on and read by means of a laser. The colorants can be applied as 20-1000 nm layers on a suitable base by vapor deposition or as a solution or dispersion, with or without the addition of a polymeric binder, by a conventional method.The layers are very stable to atmospheric influences and daylight.Type: GrantFiled: July 2, 1987Date of Patent: March 21, 1989Assignee: BASF AktiengesellschaftInventors: Reinhard Aldag, Peter Neumann
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Patent number: RE34480Abstract: Naphthalocyanine compounds represented by the general formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be the same or different, are each a straight chain or branched chain alkyl group of 5 to 12 carbon atoms and M is a metal selected from the group consisting of Cu, Ni, Mg, Pb, Pd, V, Co, .[.Nb,.]. Al, Sn, In, Fe and Ge, or its oxide, chloride or bromide, are bluish green or green crystals and are superior in absorption or near infrared rays of 750 and 850 nm, highly resistant to light, heat, acids and alkalis, soluble in organic acids, liquid crystals and resins, and accordingly are very useful as a dyestuff capable of absorbing near infrared rays.Type: GrantFiled: September 3, 1992Date of Patent: December 14, 1993Assignee: Yamamoto Kagaku Gosei Co., Ltd.Inventor: Tsunehito Eda