Boron, Germanium, Phosphorus Or Silicon Containing Patents (Class 540/128)
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Publication number: 20030170178Abstract: The present invention is directed tometal-phthalocyanines of general formula (I) to the corresponding conjugates, the processes for their preparation and use in the photodynamic therapy of microbial infections (viral, bacterial and mycotic), tumor, pre-cancerous and proliferative pathologies and/or in the diagnosis, as well as for blood and blood derivatives sterilization.Type: ApplicationFiled: December 16, 2002Publication date: September 11, 2003Inventors: Gabrio Roncucci, Lia Fantetti, Maria Paola De Filippis, Donata Dei, Giulio Jori
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Patent number: 6593286Abstract: Consumer product compositions such as laundry detergents comprising selected photosensitive compounds for photobleaching, photodisinfection, antibacterial activity, hueing or other benefits. The compositions are preferably formulated with detersive surfactants and/or water-soluble polymers.Type: GrantFiled: January 23, 2002Date of Patent: July 15, 2003Assignee: Case Western Reserve UniversityInventors: Malcolm Edward Kenney, Ying-Syi Li, Rafael Ortiz, David Johnathan Kitko, Michael Eugene Burns
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Publication number: 20030092907Abstract: The present invention is phthalocyanine compounds with peripheral siloxane substitution, as well as methods for making these compounds and various uses thereof, having the basic structure: 1Type: ApplicationFiled: September 25, 2002Publication date: May 15, 2003Inventors: Arthur W. Snow, James S. Shirk, Eva M. Maya, Richard G.S. Pong, Steven R. Flom
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Patent number: 6498249Abstract: The present invention is phthalocyanine compounds with peripheral siloxane substitution, as well as methods for making these compounds and various uses thereof, having the basic structure: wherein —W—X—Y—Z are peripheral groups comprising individual W, X, Y, and Z subgroups; W is a linkage represented by the formula: —D—(R1)0,1—, where D=S or O; X is: —(CH2)n—, n=2 to 8; Y is a siloxane chain; Z is an aryl or alkyl terminal cap; M is two protons or a metal ion; and forms a transparent film of high optical quality with large nonlinear absorption and thermal refraction, free of scattering from solid or liquid crystalline domains making them highly suitable for use as the active component in thin films, protective eye wear, and optical data storage applications.Type: GrantFiled: June 22, 2001Date of Patent: December 24, 2002Assignee: The United States of America as represented by the Secretary of the NavyInventors: Arthur W. Snow, James S. Shirk, Eva M. Maya, Richard G. S. Pong, Steven R. Flom
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Patent number: 6476219Abstract: Disclosed is a process for preparing a colorant of the formula wherein M is an atom or group of atoms capable of bonding to the central cavity of a phthalocyanine molecule, wherein axial ligands optionally can be attached to M, which comprises (a) reacting 3-n-pentadecylphenol with 4-nitrophthalonitrile in the presence of a base to form an alkylarylether adduct of phthalonitrile; and (b) reacting the alkylarylether adduct of phthalonitrile with either (i) a metal compound, or (ii) an ammonia-releasing compound in the presence of an alkanolamine solvent, or (iii) mixtures of (i) and (ii), to form the colorant.Type: GrantFiled: February 8, 2002Date of Patent: November 5, 2002Assignee: Xerox CorporationInventors: James M. Duff, James D. Mayo, Roger E. Gaynor, Jeffrey H. Banning, Michael B. Meinhardt, Randall R. Bridgeman, Nan-Xing Hu, Carol A. Jennings, Marko D. Saban, Paul F. Smith, Hadi K. Mahabadi
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Patent number: 6472523Abstract: Disclosed are compounds of the formula wherein M is an atom or group of atoms capable of bonding to the central cavity of a phthalocyanine molecule, wherein axial ligands optionally can be attached to M.Type: GrantFiled: February 8, 2002Date of Patent: October 29, 2002Assignee: Xerox CorporationInventors: Jeffrey H. Banning, Nan-Xing Hu, James D. Mayo, James M. Duff, Roger E. Gaynor, Rosa M. Duque, Nam S. Ro
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Patent number: 6462008Abstract: Detergent compositions comprising photobleach delivery systems, processes for preparing them, and their methods of use, the compositions combine selected hydrophobic photobleaches, especially based on Si(IV) phthalocyanines, with selected axial ligands, with certain water-soluble polymers, nonbonded ligands, detersuve surfactants, especially certain mid-chain branched types, and non-surfactant detersive adjuncts.Type: GrantFiled: December 21, 2001Date of Patent: October 8, 2002Assignee: Case Western Reserve UniversityInventors: Rafael Ortiz, David Johnathan Kitko, Michael Eugene Burns, Stephen Wayne Heinzman, Alan David Willey, Brian Jeffreys, James Charles Theophile Roger Burckett-St. Laurent, Phillip Kyle Vinson, Trace Wendell de Guzman Trajano
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Publication number: 20020076648Abstract: The invention relates to an optical data medium containing a preferably transparent substrate that is optionally already coated with one or more reflective layers and on the surface of which have been applied:Type: ApplicationFiled: September 20, 2001Publication date: June 20, 2002Inventors: Horst Berneth, Karl-Friedrich Bruder, Wilfried Haese, Karin Hassenruck, Serguei Kostromine, Peter Landenberger, Thomas Sommermann, Josef-Walter Stawitz, Rainer Hagen, Rafael Oser
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Publication number: 20020061602Abstract: Water soluble hybrid phthalocyanine derivatives useful in competitive and noncompetitive assays immunoassays, nucleic acid and assays are disclosed and claimed having (1) at least one donor subunit with a desired excitation peak; and (2) at least one acceptor subunit with a desired emission peak, wherein said derivative(s) is/are capable of intramolecular energy transfer from said donor subunit to said acceptor subunit. Such derivatives also may contain an electron transfer subunit. Axial ligands may be covalently bound to the metals contained in the water soluble hybrid phthalocyanine derivatives. Ligands, ligand analogues, polypeptides, proteins and nucleic acids can be linked to the axial ligands of the dyes to form dye conjugates useful in immunoassays and nucleic acid assays.Type: ApplicationFiled: February 1, 2001Publication date: May 23, 2002Inventors: Kenneth F. Buechler, Joseph B. Noar, Lema Tadesse
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Patent number: 6391505Abstract: Disclosed are a phthalocyanine crystal in which an organic acceptor compound is associated with a phthalocyanine molecule, wherein said organic acceptor compound has a reduction potential to a reference electrode (Ag+/Ag) is not less than −1.5 V and not more than −0.5 V, and an electrophotosensitive material containing said phthalocyanine crystal as an electric charge generating material, which exhibits sufficient photosensitivity even in high-speed image forming apparatuses.Type: GrantFiled: July 27, 2000Date of Patent: May 21, 2002Assignee: Kyocera Mita CorporationInventors: Kazunari Hamasaki, Yukimasa Watanabe
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Patent number: 6340745Abstract: Phthalocyanines of the formula where Me is twice hydrogen, twice lithium, magnesium, zinc, copper, nickel, VO, TiO, AlCl, AlOH, AlOCOCH3, AlOCOCF3, SiCl2 or Si(OH)2, at least four of the radicals R1 to R16 are each independently of the others a five- or six-membered saturated nitrogen-containing heterocyclic radical which is bonded to the phthalocyanine structure via a ring nitrogen atom and which can additionally contain further hetero atoms, and any remaining radicals R1 to R16 are each hydrogen, halogen, hydroxysulfonyl or C1-C4-dialkylsulfamoyl, subject to the proviso that tetrakispiperidinylphthalocyanine shall be excluded, and heterocyclyl-substituted phthalocyanines are useful for marking liquids, in particular mineral oils.Type: GrantFiled: November 19, 1999Date of Patent: January 22, 2002Assignee: BASF AktiengesellschaftInventors: Frank Meyer, Christos Vamvakaris, Karin Heidrun Beck, Gerhard Wagenblast, Bernhard Albert
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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: 6297207Abstract: The invention relates to photochemical singlet oxygen generators useful as bleaching agents or anti-microbial agents in laundry detergent compositions or in hard surface cleaning compositions. The singlet oxygen generators described herein have enhanced singlet oxygen generation due to aromatic moieties teed to the molecules, said aromatic moieties absorbing ultra violet radiation then re-emitting the radiation as fluorescence at a wavelength absorbable by the singlet oxygen producing photosensitizer unit. The increase in the number of photons having an absorbable wavelength provides an increase in the production of singlet oxygen.Type: GrantFiled: July 23, 1999Date of Patent: October 2, 2001Assignee: Case Western Reserve UniversityInventors: Alan David Willey, Anthony Harriman, Brian Jeffreys, David William Ingram
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Patent number: 6232281Abstract: The present invention relates to photochemical singlet oxygen generators useful as bleaching agents for laundry detergent compositions or in hard surface cleaning compositions and as anti-microbials. The photochemical singlet oxygen generators comprise a heavy atom unit-containing axial unit wherein the heavy atoms overlap with the &pgr; electron cloud of the photosensitizer unit and enhance the quantum efficiency of the transition of an electron from exited singlet state to triplet state.Type: GrantFiled: July 23, 1999Date of Patent: May 15, 2001Assignee: Procter & Gamble Co.Inventors: Alan David Willey, Brian Jeffreys, David William Ingram
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Patent number: 6225273Abstract: Disclosed are photochemical super oxide generators useful as photobleaches for laundry detergent compositions and as photobleaches or photodisinfectants for use in hard surface cleaning compositions. The compounds described herein comprise an amino-containing electron transfer moiety bonded to the photosensitizing unit wherein the amino-containing moiety is capable of transferring an electron to the photochemically excited &pgr; electron cloud of the photosensitizer unit thereby enabling superoxide formation.Type: GrantFiled: July 23, 1999Date of Patent: May 1, 2001Assignee: Case Western Reserve UniversityInventors: Alan David Willey, Anthony Harriman
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Patent number: 6127543Abstract: Organometallic iron complexes containing one or more basic structural components characterizing a molecule with antimalarial properties such as quinine, chloroquinine or mepacrine, as well as one or more iron atoms are described. The complexes of the invention are more particularly characterized in that they contain one or more ferrocene groups.Type: GrantFiled: January 29, 1998Date of Patent: October 3, 2000Assignee: Universite des Sciences et Technologies de LilleInventors: Jacques Brocard, Jacques Lebibi, Lucien Maciejewski
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Patent number: 6060598Abstract: Fluorescence immunoassays methods are provided which use fluorescent dyes which are free of aggregation and serum binding. Such immunoassay methods are thus, particularly useful for the assay of biological fluids, such as serum, plasma, whole blood and urine.Type: GrantFiled: June 13, 1997Date of Patent: May 9, 2000Assignee: Hyperion, Inc.Inventors: Robert Francis Devlin, Walter Beach Dandliker, Peter Olaf Gustaf Arrhenius
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Patent number: 6057071Abstract: An electrophotographic photoreceptor which is excellent in sensitivity, durability and environmental capability comprises a photosensitive layer containing dihydroxysilicon phthalocyanine which is monoclinic and has lattice constants a=12.8.+-.1.ANG., b=14.5.+-.1.ANG., c=6.8.+-.1.ANG. and .beta.=94.4.+-.1.degree..Type: GrantFiled: December 1, 1997Date of Patent: May 2, 2000Assignee: Mitsubishi Chemical CorporationInventors: Toyoshi Ohashi, Yasuko Osano, Yuko Kojima, Ichiro Yokotake, Hitoshi Ono, Yuka Nagao, Masatomi Ozawa
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Patent number: 6013777Abstract: Compounds of formulaA(B).sub.x, (I),wherein x is an integer from 1 to 4,A is the radical of a chromophore of the quinacridone, anthraquinone, perylene, indigo, quinophthalone, isoindolinone, isoindoline, dioxazine, phthalocyanine or azo series, which radical contains x N-atoms attached to B, preferably with at least one directly adjacent or conjugated carbonyl group,B is a group of formula ##STR1## and, if x is 2, 3 or 4, may also be one, two or three hydrogen atoms. The symbols Q, R.sub.1, R.sub.2, R.sub.3, R.sub.4, X, Y, Z, m and n, are as defined in claim 1.These carbamate group-containing soluble chromophores are distinguished by outstanding solid state fluorescence in the UV range as well as the by ease with which they can be converted to the corresponding pigments in the substrate in which they are incorporated.Type: GrantFiled: June 10, 1998Date of Patent: January 11, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Zhimin Hao, John S. Zambounis, Abul Iqbal
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Patent number: 5916481Abstract: Low hue photobleaching compositions comprising organosilicon(IV) phthalocyanine and naphthalocyanines having Q-band absorption maxima at wavelengths greater than 660 nm and increased triplet state yields whereby production of singlet oxygen is increased. Use of Si.sup.4+ phthalocyanine and naphthalocyanines compounds in photobleaching compositions allows for formulation of low hue laundry compositions, bleach compositions, and hard surface cleaners.Type: GrantFiled: June 18, 1996Date of Patent: June 29, 1999Assignee: The Procter & Gamble CompanyInventor: Alan David Willey
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Patent number: 5886160Abstract: Compounds of formulaA(B).sub.x, (I),wherein x is an integer from 1 to 4,A is the radical of a chromophore of the quinacridone, anthraquinone, perylene, indigo, quinophthalone, isoindolinone, isoindoline, dioxazine, phthalocyanine or azo series, which radical contains x N-atoms attached to B, preferably with at least one directly adjacent or conjugated carbonyl group,B is a group of formula ##STR1## and, if x is 2, 3 or 4, may also be one, two or three hydrogen atoms. The symbols Q, R.sub.1, R.sub.2, R.sub.3, R.sub.4, X, Y, Z, m and n, are as defined in claim 1.These carbamate group-containing soluble chromophores are distinguished by outstanding solid state fluorescence in the UV range as well as the by ease with which they can be converted to the corresponding pigments in the substrate in which they are incorporated.Type: GrantFiled: June 12, 1998Date of Patent: March 23, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Zhimin Hao, John S. Zambounis, Abul Iqbal
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Patent number: 5872248Abstract: A simple, flexible, convenient method for making silicon phthalocyanines and naphthalocyanines by inserting silicon into metal-free phthalocyanines and metal-free naphthalocyanines is provided. The method comprises: providing a metal-free phthalocyanine or metal-free naphthalocyanine; reacting the metal-free phthalocyanine or metal-free naphthalocyanine with HSiCl.sub.3 to provide a reaction product; then reacting the reaction product with water; and extracting a silicon phthalocyanine or a silicon naphthalocyanine. The invention also relates to novel phthalocyanines and naphthalocyanines. The phthalocyanines and naphthalocyanines are useful as photosensitizers and as dyes.Type: GrantFiled: March 28, 1997Date of Patent: February 16, 1999Assignee: Case Western Reserve UniversityInventors: Gongzhen Cheng, Guolun Hao, Hongqiao Wu, Ying-Syi Li, Malcolm E. Kenney
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Patent number: 5856472Abstract: Novel aluminum phthalocyanine reactive dyestuffs of the formula (1) ##STR1## in which x is Cl or OH;Z is vinyl or a group of the formula --CH.sub.2 CH.sub.2 --Y, in which Y is a substituent which can be eliminated under alkaline conditions,c is a number from 0.5 to 4;M is a hydrogen, an alkali metal or a substituted or unsubstituted ammonium ion; andR.sup.1 and R.sup.2 independently of one another are hydrogen, substituted or unsubstituted C.sub.1 -C.sub.6 alkyl, a C.sub.1 -C.sub.6 -alkyl which is substituted by one or two radicals of the formulae OH, SO.sub.3 M or OSO.sub.Type: GrantFiled: June 16, 1997Date of Patent: January 5, 1999Assignee: DyStar Textilfarben GmbH & Co. Deutschland KGInventors: Karl-Josef Herd, Klaus Saitmacher
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Patent number: 5856471Abstract: An electrophotographic photoreceptor comprising a conductive substrate having thereon a photosensitive layer, the photosensitive layer containing a hydroxymetal or hydroxysilicon phthalocyanine pigment represented by formula (I) as a charge generating material, the phthalocyanine pigment having been treated with an orcanometallic compound having a hydrolyzable functional group or a hydrolysis product thereof: ##STR1## wherein Me represents A, Ga, In, Si, Ge or Sn; X representsH, C, Br or I; m represents an integer of from I to 4; and n represents 1 where Me is A, Ga or In, or 2 where Me is Si, Ge or Sn.Type: GrantFiled: January 29, 1997Date of Patent: January 5, 1999Assignee: Fuji Xerox Co., Ltd.Inventors: Hidemi Nukada, Takahiro Suzuki, Katsumi Nukada, Katsumi Daimon, Yasuo Sakaguchi
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Patent number: 5824799Abstract: Water soluble hybrid phthalocyanine derivatives useful in competitive and noncompetitive assays immunoassays, nucleic acid and assays are disclosed and claimed having (1) at least one donor subunit with a desired excitation peak; and (2) at least one acceptor subunit with a desired emission peak, wherein said derivative(s) is/are capable of intramolecular energy transfer from said donor subunit to said acceptor subunit. Such derivatives also may contain an electron transfer subunit. Axial ligands may be covalently bound to the metals contained in the water soluble hybrid phthalocyanine derivatives. Ligands, ligand analogs, polypeptides, proteins and nucleic acids can be linked to the axial ligands of the dyes to form dye conjugates useful in immunoassays and nucleic acid assays.Type: GrantFiled: March 22, 1996Date of Patent: October 20, 1998Assignee: Biosite Diagnostics IncorporatedInventors: Kenneth F. Buechler, Joseph B. Noar, Lema Tadesse
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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: 5811543Abstract: Compounds of the formulaA(B).sub.x (I),wherein x is an integer from 1 to 4,A is the radical of a chromophore of the phthalocyanine series, which radical contains x B groups attached to N-atoms, preferably with at least one directly adjacent to or conjugated with a carbonyl group,B is a group of the formula ##STR1## and, if x is 2,3 or 4, may also be one, two or three hydrogen atoms, wherein the symbols Q, R.sub.1, R.sub.2, R.sub.3, R.sub.4, Y, Z, m and n, are as defined in the disclosureThese carbamate group-containing soluble chromophores are distinguished by outstanding solid state fluorescence in the UV range as well as the by ease with which they can be converted to the corresponding pigments in the substrate in which they are incorporated.Type: GrantFiled: July 9, 1996Date of Patent: September 22, 1998Assignee: Ciba Speciality Chemicals CorporationInventors: Zhimin Hao, John S. Zambounis, Abul Iqbal
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Patent number: 5792860Abstract: Phthalocyanines of formula (I) are described, wherein M is a metal atom, metal compound or silicon or a compound of silicon or is 2H; R.sub.1 -R.sub.25 may be the same or different, provided that at least one of R.sub.1 -R.sub.25 has the Formula (II), wherein Y groups are independently H, C.sub.1-3 alkyl, halogen or CN; k=0 or 1; l=1-10; m=0 or 1; n=1-10; p=1-10; q=1-20; r=0 or 1; X may be H, Me, etc . . . Compounds of the above formulae are useful in a broad range of applications, including electrooptical devices, and for use in optical recording media.Type: GrantFiled: September 25, 1996Date of Patent: August 11, 1998Assignee: The Secretary of State for Defence in Her Majesty's Government of the United Kingdom of Great Britain and Northern Ireland of Defence Evaulation Research AgencyInventors: Neil Bruce McKeown, Kevin Edward Treacher, Guy James Clarkson
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Patent number: 5763602Abstract: The present invention provides improved methods for synthesizing phthalocyanines, particularly HOSiPcOSi(CH.sub.3).sub.2 (CH.sub.2).sub.3 N(CH.sub.3).sub.2, which do not involve photolysis, and which produces purity of at least about 95%, and in the preferred embodiment of the first method of synthesis provide a yield of greater than about 70% and typically greater than 80%. The first method involves a method for synthesizing a phthalocyanine compound comprising the following steps: providing a phthalocyanine precursor having a central silicon; adding a first aminosiloxy ligand to the central silicon of the phthalocyanine precursor; adding a second aminosiloxy ligand to the central silicon of the phthalocyanine precursor; displacing the second aminosiloxy ligand by an organic acid ligand, preferably Cl.sub.3 CCOO ligand; then displacing the Cl.sub.3 CCOO ligand with an HO ligand.Type: GrantFiled: October 1, 1996Date of Patent: June 9, 1998Inventors: Ying-Syi Li, Malcolm E. Kenney
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Patent number: 5739318Abstract: The present invention relates to labelling agents comprising non-proteinaceous boronic acid conjugates having absorption maxima at not less than 600 nm, said label being provided by e.g., an azine, triphenylmethane, cyanine or phthalocyanine dye. The labelling agents are useful in the estimation and quantification of cisdiols such as glycosylated haemoglobin, by virtue of the substantially total absence of overlap with the absorption spectrum of haemoglobin. Oxazine and thiazine dyes exhibiting similar absorption characteristics and containing other activated moieties are similarly useful labelling agents, especially in the presence of haemoglobin.Type: GrantFiled: July 12, 1993Date of Patent: April 14, 1998Assignee: Axis Research ASInventors: Frank Frantzen, Erling Sundrehagen
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Patent number: 5739319Abstract: A green or near infrared light absorbing water-soluble phthalocyanine or naphthalocyanine derivative which has excellent water resistance after dyeing, is provided. The present invention provides a phthalocyanine or naphthalocyanine derivative represented by the formula: ##STR1## wherein X represents a halogen atom substituted at nucleus; M represents two hydrogen atoms, a divalent metal atom, a trivalent mono-substituted metal atom, or a tetravalent di-substituted metal atom; m represents 4 or 8; and n represents an integer of 0 to 12.Type: GrantFiled: September 13, 1996Date of Patent: April 14, 1998Assignee: Orient Chemical Industries, Ltd.Inventor: Yasuhiro Yamasaki
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Patent number: 5703229Abstract: Provided are new compounds useful as near infrared fluorophoric markers. In the practice of this invention a method is also provided for tagging thermoplastic containers using near infrared fluorescing compounds or copolymerized residues readily capable of detection. The new compounds are phthalocyanine and naphthalocyanine derivatives which are covalently bonded to substituted silicon and aluminum compounds. The methods, compositions, and compounds described herein thus provide a total system useful for marking, for identification purposes, the various classes of thermoplastic wastes, so that they can be identified, sorted, and subsequently recycled.Type: GrantFiled: February 29, 1996Date of Patent: December 30, 1997Assignee: Eastman Chemical CompanyInventors: James J. Krutak, Michael R. Cushman, Clarence A. Coates, William W. Parham, Max A. Weaver, Gabor Patonay
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Patent number: 5702952Abstract: The invention provides novel labelled boronic acid conjugates of formula ##STR1## (wherein V is a reporter moiety; W.sup.2 is a bond or an organic linker moiety;W.sup.1 is a *SO.sub.2 NR.sup.2, *CONR.sup.2 or *CH.sub.2 N.sup..sym. R.sup.2.sub.2 group bound at the *-marked atom to the phenyl ring;R.sup.1 is hydrogen or an electron withdrawing substituent group; andeach R.sup.2 independently is hydrogen or an optionally hydroxylated and optionally C.sub.1-6 -alkoxylated C.sub.1-6 -alkyl group) and salts thereof, e.g. for use in assays for cis-diols such as glycated blood proteins, having enhanced water-solubility and storage stability.Type: GrantFiled: February 21, 1997Date of Patent: December 30, 1997Assignee: Axis Biochemicals ASAInventors: Erling Sundrehagen, Frank Frantzen
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Patent number: 5686439Abstract: Phthalocyanine-chelate complexes of formula I ##STR1## are described which contain as central atom M aluminium, gallium, indium, tin, ruthenium or preferably germanium and in which the remaining symbols are as defined in claim 1. The complexes can be used inter alia in the photodynamic chemotherapy of tumours.Type: GrantFiled: December 15, 1995Date of Patent: November 11, 1997Assignee: Novartis CorporationInventors: Hans Georg Capraro, Marcus Baumann
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Patent number: 5677199Abstract: Marker components are provided which are compatible with aqueous solutions, exhibit favorable fluorescence properties and exhibit decreased non-specific binding to macromolecules in solution. These marker components are useful in applications such as fluorescence immunoassays and in vivo imaging.Type: GrantFiled: November 29, 1994Date of Patent: October 14, 1997Assignee: Diatron CorporationInventor: Peter Olof Gustaf Arrhenuis
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Patent number: 5670491Abstract: Phthalocyanine chelate complexes of formula I ##STR1## are described which contain as central atom M aluminum; gallium, indium, tin, ruthenium or preferably germanium and in which the remaining symbols are as defined in claim 1. The complexes can be used inter alia in the photodynamic chemotherapy of tumors.Type: GrantFiled: June 30, 1994Date of Patent: September 23, 1997Assignee: Ciba-Geigy CorporationInventors: Hans Georg Capraro, Marcus Baumann
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Patent number: 5656751Abstract: Disclosed is a dichroic crystal including at least one member selected from the group consisting of phtharocyanine, a phtharocyanine derivative, phtharocyanine with a central metal introduced therein, a phtharocyanine derivative with a central metal introduced therein, and iodine. It is precipitated when the iodine is added to a solution containing the member, and it includes the iodine in a form of I.sub.3.sup.- and I.sub.5.sup.- ions. It not only has a high dichroic property but also superb heat resistance and weatherability, so that it is applicable to suspended particles display devices used in severe environments.Type: GrantFiled: April 17, 1996Date of Patent: August 12, 1997Assignee: Kabushiki Kaisha Toyota Chuo KenkyushoInventors: Hiromitsu Tanaka, Hisato Takeuchi, Arimitsu Usuki, Kazuo Tojima, Atsushi Shirasawa, Ai Kobayashi
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Patent number: 5646273Abstract: A phthalocyanine represented by the formula (1) ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 is independently an alkyl group substituted by 0 to 5 halogen atoms and having 1 to 20 carbon atoms, an alkenyl group substituted by 0 to 5 halogen atoms and having 2 to 20 carbon atoms or an alkynyl group substituted by 0 to 5 halogen atoms and having 2 to 20 carbon atoms, and at least one of R.sup.1, R.sup.2, R.sup.3 and R.sup.Type: GrantFiled: September 20, 1995Date of Patent: July 8, 1997Assignees: Mitsui Toatsu Chemicals, Inc., Yamamoto Chemicals, Inc.Inventors: Takahisa Oguchi, Hideki Umehara, Kenichi Sugimoto, Ryu Oi, Hisato Itoh
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Patent number: 5641878Abstract: Fluorescent dyes which are free of aggregation and serum binding are provided. These dyes are suitable for applications such as fluorescence immunoassays, in vivo imaging and in vivo tumor therapy. The dyes are particularly useful in fluorescence immunoassays of biological samples containing serum. Such dyes have two polyoxyhydrocarbyl moities, one located on either side of a planar molecular structure such as a porphyrin derivative, azaporphyrin derivative, corrin derivative, sapphyrin derivative or porphycene derivative.Type: GrantFiled: November 2, 1994Date of Patent: June 24, 1997Assignee: Diatron CorporationInventors: Walter B. Dandliker, Mao-Lin Hsu
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Patent number: 5641879Abstract: The invention relates to phthalocyanines and metal complexes thereof with divalent metals or divalent oxo metals, which contain at least one phosphorus-containing substituent bonded to the peripheral carbon skeleton via the phosphorus atom.The compounds preferably conform to the general structural formula (G).sub.k -A-(Q).sub.l, in which A is a phthalocyanine or metal complex thereof with a divalent metal or a divalent oxo metal, G is a phosphorus-containing substituent, Q is a further substituent as defined below, the index k is a number from 1 to 16, and l, independently thereof, is 0 or a number from 1 to 15, with the proviso that the sum of k and l is a number less than or equal to 16.The invention also relates to a material for the optical recording and storage of information, in which at least one storage layer (2) of a novel phthalocyanine compound or a metal complex thereof has been applied to a transparent, dielectric carrier material (1).Type: GrantFiled: September 20, 1995Date of Patent: June 24, 1997Assignee: Ciba-Geigy CorporationInventors: Heinz Wolleb, Hanspeter Preiswerk, Beat Schmidhalter, Heinz Spahni
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Patent number: 5631364Abstract: The invention provides novel labelled boronic acid conjugates of formula ##STR1## (wherein V is a reporter moiety; W.sup.2 is a bond or an organic linker moiety;W.sup.1 is a *SO.sub.2 NR.sup.2, *CON.sup.2 or *CH.sub.2 N.sym.R.sup.2 .sub.2 group bound at the *-marked atom to the phenyl ring;R.sup.1 is hydrogen or an electron withdrawing substituent group; andeach R.sup.2 independently is hydrogen or an optionally hydroxylated and optionally C.sub.1-6 -alkoxylated C.sub.1-6 -alkyl group) and salts thereof, e.g. for use in assays for cis-diols such as glycated blood proteins, having enhanced water-solubility and storage stability.Type: GrantFiled: March 31, 1994Date of Patent: May 20, 1997Assignee: AXIS Biochemicals ASAInventors: Erling Sundrehagen, Frank Frantzen
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Patent number: 5491228Abstract: A process for the preparation of dihydroxygermanium phthalocyanine, polymorphic Type III, which comprises treating dihalogermanium phthalocyanine or dialkoxygermanium phthalocyanine with a strong acid, followed by treatment with water, optionally washing with a dilute aqueous base and water, and subsequently optionally admixing with a solvent mixture comprised of a strong organic acid and aprotic organic solvent.Type: GrantFiled: April 18, 1994Date of Patent: February 13, 1996Assignee: Xerox CorporationInventors: Beng S. Ong, Cheng-Kuo Hsiao
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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: 5484778Abstract: The present invention relates to a series of novel phthalocyanine compositions (or compounds) suitable for use as photosensitizers for photodynamic therapy. Specifically, the invention relates to a series of new aluminum (Al) germanium (Ge), gallium (Ga), tin (Sn) and/or silicon (Si) phthalocyanines having substituted amine or quaternary ammonium axial ligands attached to the central metal, and the use of these new phthalocyanine compositions for the treatment of cancer through photosensitization. Moreover, the present invention is directed to the methods of preparing these compositions for use in photodynamic therapy.Type: GrantFiled: September 2, 1993Date of Patent: January 16, 1996Assignee: University Hospitals of ClevelandInventors: Malcolm E. Kenney, Nancy L. Oleinick, Boris D. Rihter, Ying-Syi Li
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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: 5438135Abstract: Water-soluble tetraazaporphins with novel structure is suitable as a fluorochrome for labeling and provides a reagent usable for fluorescence analysis process.Type: GrantFiled: March 5, 1992Date of Patent: August 1, 1995Assignee: Hitachi Chemical CompanyInventors: Seiji Tai, Mitsuo Katayose, Hiroo Watanabe
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Patent number: 5428152Abstract: Disclosed are naphthalocyanine compounds having siloxy groups bonded to a central metal silicon. The compounds can be used as a charge generating substance of an electrophotographic plate having high sensitivity to the longer wavelength light of about 800 nm without conducting a special treatment. The naphthalocyanine compounds are represented by the formula: ##STR1## wherein L is a group of the formula R.sub.1 R.sub.2 R.sub.3 SiO--, and R.sub.1, R.sub.2 and R.sub.3 are each a same alkyl group having 1-3 carbon atoms.Type: GrantFiled: June 10, 1993Date of Patent: June 27, 1995Assignee: Hitachi Chemical Company, Ltd.Inventors: Shigeru Hayashida, Seiji Tai
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Patent number: 5403928Abstract: Marker components are provided which are compatible with aqueous solutions, exhibit favorable fluorescence properties and exhibit decreased non-specific binding to macromolecules in solution. These marker components are useful in applications such as fluorescence immunoassays, in vivo imaging and in vivo tumor therapy.Type: GrantFiled: May 15, 1991Date of Patent: April 4, 1995Assignee: Diatron CorporationInventor: Peter O. G. Arrhenuis
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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: H1695Abstract: A one-step method of manufacturing soluble phthalocyanines and metallophthalocyanines, like zinc phthalocyanine, by converting a phthalocyanine or a metallophthalocyanine to a trialkylsilyl-substituted derivative is disclosed. The phthalocyanine or metallophthalocyanine is converted to a soluble trialkylsilyl-substituted derivative by interacting the phthalocyanine or metallophthalocyanine with an active metal amide, like lithium 2,2,6,6-tetramethylpiperidide, and a halotrialkylsilane, like chlorotrimethylsilane, to provide a phthalocyanine compound, like phthalocyanine monomers, dimers or polymers, metalated or unmetalated, that are soluble in organic media.Type: GrantFiled: June 1, 1990Date of Patent: November 4, 1997Assignee: The United States of America as represented by the United States Department of EnergyInventors: Jerome W. Rathke, Michael J. Chen, Carol M. Fendrick