Nitrogen Attached Indirectly To Ring Carbon Of The Phthalocyanine Ring System By Acyclic Nonionic Bonding Patents (Class 540/135)
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Patent number: 10568963Abstract: A composition comprising PAA nanoparticles containing a post loaded tetrapyrollic photosensitizer and a postloaded imaging agent and methods for making and using same.Type: GrantFiled: August 3, 2012Date of Patent: February 25, 2020Assignees: HEALTH RESEARCH, INC., HE RESEARCH FOUNDATION OF STATE UNIVERSITY OF NEW YORK, REGENTS OF THE UNIVERSITY OF MICHIGANInventors: Ravindra K. Pandey, Raoul Kopelman, Anurag Gupta, Munawwar Sajjad
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Patent number: 9034095Abstract: An object is to overcome the drawbacks of conventional blue phthalocyanine pigments upon the formation of images, and to develop a blue pigment that can satisfactorily exhibit a greenish blue color high in chroma and excellent in colorfulness, brightness, dispersibility, hue, tinting power and the like and that is applicable to various image recording methods. The object can be achieved by a greenish blue pigment, which exhibits a greenish blue hue of high chroma and contains a pigment represented by the following formula (I): wherein the number, m, of substituent phthalimidomethyl group(s) is in a range of 1.0?m?5.0, and the number, n, of a substituent sulfonic group R1 is in a range of 0.05?n?1.0.Type: GrantFiled: July 19, 2012Date of Patent: May 19, 2015Assignee: DAINICHISEIKA COLOR & CHEMICALS MFG. CO., LTD.Inventors: Koji Tsuchiya, Masahiko Aoba, Kenjiro Matsumoto, Takeshi Tamaki
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Patent number: 8808439Abstract: A water-soluble phthalocyanine dye or naphthalocyanine dye with near-infrared absorption comprises at least one complexed unit. Each unit comprises a phthalocyanine or a naphthalocyanine moiety and a metal atom complexed thereto and having a valency of at least three, with two valencies complexed to the phthalocynanine ring or the naphthalocyanine ring, each unit joined to another through a fused ring, at least one valency attached to water-soluble axial ligands. The dyes to may be employed in inkjet inks in conjunction with colorants.Type: GrantFiled: July 31, 2009Date of Patent: August 19, 2014Assignee: Hewlett-Packard Development Company, L.P.Inventors: Sivapackia Ganapathiappan, Jayprakash Bhatt
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Patent number: 8586198Abstract: A dendritic molecule represented by Formula 3: where Pc is metal phthalocyanine represented by Formula 2: where M is a core metal of the dendritic molecule; n is an integer in the range of 1 to 50; each of the Xs is a bivalent linking group independently selected from the group consisting of O, S, CH2, CO, SO2 and NHCO; and each of the Rs is independently selected from the group consisting of CN, COOH, SO3H and PO3H. The dendritic molecule containing metal phthalocyanine is dissolved in an organic solvent, and thus can be used to easily form a hole injection layer or a hole transport layer using solution deposition. The hole injection layer comprising the dendritic molecule containing metal phthalocyanine has good adhesion to an electrode and improved hole injection ability. The organic light emitting diode including the hole injection layer exhibits high luminance and emitting efficiency.Type: GrantFiled: November 28, 2007Date of Patent: November 19, 2013Assignee: Samsung Display Co., Ltd.Inventors: Tae-Woo Lee, Jong-Jin Park, Lyong-Sun Pu, Masa-Aki Kakimoto
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Publication number: 20120267612Abstract: Cross-linkable copper complexes comprising a copper phthalocyanine core and one or more cross-linkable functionalities linked to the phthalocyanine core. The copper complex may have a spacer group with the one or more cross-linkable functionalities on the spacer group. The spacer group contains a chain or one or more aryl groups. These cross-linkable copper complexes may be used in making organic electronic devices, such as OLEDs, by solution processing techniques.Type: ApplicationFiled: January 14, 2009Publication date: October 25, 2012Applicant: UNIVERSAL DISPLAY CORPORATIONInventors: Chuanjun Xia, Raymond Kwong, Ken-Tsung Wong, Hsiao-Fan Chen, Ming-Chen Kuo, Kwang-Ohk Cheon
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Patent number: 8221657Abstract: The instant invention relates to novel phthalocyanines and their use as IR-absorbers, in particular in transparent thermoplastic or crosslinkable polymers. A further aspect of the invention is a composition of these phthalocyanines and thermoplastic or crosslinkable polymers and an architectural or automotive glazing containing these phthatolcyanines.Type: GrantFiled: June 3, 2011Date of Patent: July 17, 2012Assignee: BASF SEInventors: Francesca Peri, Cesare Lorenzetti, Samanta Cimitan, Markus Grob
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Patent number: 8034531Abstract: The present invention relates to a photosensitive resin composition comprising a) as a component (A) a green colorant of the formula (I) in which the rings A, B, C and D are substituted by hydroxy or by moiety wherein R, is hydrogen or C1,-C4.-Alkyl, R2 is hydrogen or C1,-C4-Alkyl, n is 0, 1, 2 or 3 and the ring E is unsubstituted or substituted by C1,-C6alkyl, C1,-C6alkoxy, hydroxy, NHCOR3, NHSO2, R4 or SO2NHR5, wherein R3, is C1,-C4,-Alkyl or phenyl, R4, is C1,-C4-Alkyl or phenyl and R5 is C1,-C4-Alkyl or phenyl, b) as a component (B) an alkali soluble oligomer or polymer (reactive or unreactive), c) as a component (C) a polymerizable monomer, d) as a component (D) a photoinitiator, e) as a component (E) an epoxy compound, and also, if desired, f) as a component (F) further additives, used as solder resist, etching resist or plating resist in the manufacture of printed circuit boards.Type: GrantFiled: November 19, 2003Date of Patent: October 11, 2011Assignee: BASF SEInventors: Hidetaka Oka, Jean-Marie Adam
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Publication number: 20090255986Abstract: A method of initiating a requested action in a computer system via a printed substrate. The substrate contains human-readable information and machine-readable coded data. The method includes the steps of: positioning a sensing device in an operative position relative to the substrate; sensing the coded data; generating indicating data in the sensing device using the sensed coded data; and sending the indicating data to the computer system. The coded data comprises a phthalocyanine salt comprising one or more sulfonate groups. A counterion of at least one sulfonate group is an ammonium cation comprising at least 20 carbon atoms.Type: ApplicationFiled: June 28, 2009Publication date: October 15, 2009Inventors: Scott Matthew Starling, Simone Charlotte Vonwiller, Damon Donald Ridley, Kia Silverbrook
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Publication number: 20090226687Abstract: A composition comprising: (a) a dye component comprising a major dye component which is the salt of a mixture of phthalocyanine dyes of Formula (1) with an organic compound carrying two or more acidic groups: wherein: M is Cu or Ni; Pc represents a phthalocyanine R1 and R2 independently are H or methyl; R3 is H, methyl or optionally substituted C1-8alkylNR5R6; R4 is optionally substituted C1-8alkylNR5R6; R5 is H or optionally substituted C1-4alkyl; R6 is H or optionally substituted C1-4alkyl; x is 0 to 3.9; y is 0 to 3.9; z is 0.1 to 4.0 the sum of (x+y+z) is 2 to 4; and the substituents, represented by x, y and z are attached to a ? position on the phthalocyanine ring; and (b) a liquid medium. Also ink-jet printing processes, printed materials, ink-jet cartridges and new dye salts.Type: ApplicationFiled: September 29, 2006Publication date: September 10, 2009Inventor: Thomas Paul
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Patent number: 7566363Abstract: A phthalocyanine phthalocyanine salt suitable for formulation in a solvent-based or oil-based ink vehicle is disclosed. The phthalocyanine comprises one or more sulfonate groups and a counterion of at least one sulfonate group is an ammonium cation comprising at least 15 carbon atoms. Ammonium salts of sulfonated gallium naphthalocyanines exemplify such phthalocyanine salts.Type: GrantFiled: May 13, 2008Date of Patent: July 28, 2009Assignee: Silverbrook Research Pty LtdInventors: Scott Matthew Starling, Simone Charlotte Vonwiller, Damon Donald Ridley, Kia Silverbrook
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Publication number: 20090043090Abstract: A compound having preferential localization in tumor tissue relative to normal tissue, a preferential electromagnetic absorption at a wavelength between about 660 and 900 nm, and a fluorescence at a wavelength shifted from the preferential absorption by at least +30 nm and preferably at least +50 nm. The compound further preferably destroys tumor tissue in which it is absorbed when exposed to light at its preferential absorption wavelength. In a preferred embodiment of the invention, the compound is a conjugate of a tumor avid tetrapyrrole compound with a fluorescent dye, and more preferably the fluorescent dye is an indocyanine dye such as indocyanine green. The tumor avid tetrapyrrole compound is preferably a porphyrin derivative selected from the group consisting of chlorins, bacteriochlorins, purpurins and derivatives thereof.Type: ApplicationFiled: July 13, 2005Publication date: February 12, 2009Applicant: HEALTH RESEARCH, INC.Inventors: Ravindra K. Pandey, Yihui Chen, William Potter, Allan Oseroff
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Patent number: 7459016Abstract: A method for the production of a phthalocyanine pigment preparation includes finely distributing a crude phthalocyanine pigment by dry milling, wet milling, salt kneading, acid pasting or acid swelling to give a pre-pigment, the pre-pigment is subjected to a finishing treatment in a mixture of water and an organic solvent at alkaline pH, increased temperature and in the presence of at least one pigment dispersant from the group of phthalocyanine sulphonic acids, phthalocyanine carboxylic acids, phthalocyanine sulphonate salts, phthalocyanine carboxylate salts and phthalocyanine suiphonamides.Type: GrantFiled: November 27, 2003Date of Patent: December 2, 2008Assignee: Clariant Produkte (Deutschland) GmbHInventors: Klaus Brychcy, Joachim Weber, Heidrun Mehler
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Publication number: 20080199732Abstract: A dendritic molecule represented by Formula 3: where Pc is metal phthalocyanine represented by Formula 2: where M is a core metal of the dendritic molecule; n is an integer in the range of 1 to 50; each of the Xs is a bivalent linking group independently selected from the group consisting of O, S, CH2, CO, SO2 and NHCO; and each of the Rs is independently selected from the group consisting of CN, COOH, SO3H and PO3H. The dendritic molecule containing metal phthalocyanine is dissolved in an organic solvent, and thus can be used to easily form a hole injection layer or a hole transport layer using solution deposition. The hole injection layer comprising the dendritic molecule containing metal phthalocyanine has good adhesion to an electrode and improved hole injection ability. The organic light emitting diode including the hole injection layer exhibits high luminance and emitting efficiency.Type: ApplicationFiled: November 28, 2007Publication date: August 21, 2008Inventors: Tae-Woo Lee, Jong-Jin Park, Lyong-Sun Pu, Masa-Aki Kakimoto
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Patent number: 7332261Abstract: A phthalocyanine compound represented by the following general formula (I) and the mixture thereof, and an optical recording medium containing the compound/mixture in its recording layer. wherein in formula (I), M is two hydrogen atoms, a divalent metal atom, a mono-substituted trivalent metal atom, a di-substituted tetravalent metal atom, or an oxymetal, and L1, L2, L3 and L4 are each independently formula (a), formula (b), or formula (c): wherein X, Y, Z and R are defined.Type: GrantFiled: February 14, 2003Date of Patent: February 19, 2008Assignee: Ciba Specialty Chemicals CorporationInventors: Kazuhiro Seino, Shinichi Nakagawa, Tsutami Misawa, Satoshi Kinoshita, Akihiro Kosaka, Hiroshi Terao, Yojiro Kumagae
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Patent number: 7265100Abstract: The present invention refers to a process for the separation of regioisomeric mixtures of metal phthalocyanines of formula (I), to the regioisomers obtained by this process, and their use as phototherapeutic and photodiagnostic agentsType: GrantFiled: October 28, 2002Date of Patent: September 4, 2007Assignee: L. Molteni & C. Dei Fratelli Alitti Societa' di Esercizio S.p.A.Inventors: Gabrio Roncucci, Francesca Giuntini, Donata Dei, Maria Paola De Filippis, Paolo Sarri, Marco Possenti, Valentina Paschetta, Giacomo Chiti
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Titanyl phthalocyanine crystal and production method of the same, and electrophotosensitive material
Publication number: 20040049027Abstract: The present invention relates to a novel titanyl phthalocyanine crystal which can prepare a coating solution having excellent storage stability because it satisfies both of the following two characteristics (a) and (b), a method of producing the same, an electrophotosensitive material using the above crystal as an electric charge generating material.Type: ApplicationFiled: August 27, 2003Publication date: March 11, 2004Inventors: Kazunari Hamasaki, Daisuke Kuboshima, Hisakazu Honma, Jun Azuma, Eiichi Miyamoto -
Publication number: 20030234995Abstract: A phthalocyanine compound (1) of a specific structure excelling in ability to absorb near infrared, ability to effect selective absorption of near infrared radiation particularly in a wavelength range exceeding 920 nm and falling short of 1050 nm, solubility in a solvent as well, compatibility with resin, and in such characteristic properties as heat resistance, light resistance, and weatherability, and a near infrared absorbing filter characterized by using the phthalocyanine compound (1) and phthalocyanine compound (2) having a maximum absorption wavelength at least in the range of 800-920 nm are provided. It enjoys a long service life and permits extensive use without selecting a substrate.Type: ApplicationFiled: June 10, 2003Publication date: December 25, 2003Inventors: Kiyoshi Masuda, Masunori Kitao
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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: 6589325Abstract: An object of the present invention is to provide a novel phthalocyanine compound or the salt thereof as a black colorant that has a hue suitable for ink-jet recording and can provide a recorded material with strong light fastness and water fastness, an ink composition containing the compound, an ink-jet recording method using the ink composition, a tank containing the ink composition, an ink-jet printer set with the tank, and a colored product colored by the colorant. The novel phthalocyanine compound or the salt thereof can be easily obtained by reacting an aminophthalocyanine with (meth)acrylic acid.Type: GrantFiled: October 9, 2001Date of Patent: July 8, 2003Assignee: Nippon Kayaku Kabushiki KaishaInventors: Yoshinori Katoh, Hirokazu Kitayama, Yasuo Shirasaki
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Publication number: 20030017164Abstract: The present invention discloses dye-azide derivatives and their bioconjugates for dual phototherapy of tumors and other lesions. The compounds of the present invention may contain either a mixture of Type 1 and Type 2 agents or a single entity that integrates both units in the same molecules. The compounds are designed to produce both Type 1 and Type 2 phototherapeutic effect at once using dual wavelength light source that will produce singlet oxygen and nitrene at the lesion of interest.Type: ApplicationFiled: July 3, 2001Publication date: January 23, 2003Applicant: MALLINCKRODT INC.Inventors: Raghavan Rajagopalan, Samuel I. Achilefu, Joseph E. Bugaj, Richard B. Dorshow
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Patent number: 6423839Abstract: This invention relates to substituted azophthalocyanine pigment precursors which produce uniform mixed colors when their solubilising groups are eliminated.Type: GrantFiled: March 22, 2000Date of Patent: July 23, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Véronique Hall-Goulle, Gerardus De Keyzer
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Patent number: 6221137Abstract: Phase change inks containing at least one colorant that comprises at least one metal phthalocyanine tetraamide chromogen, at least one metal phthalocyanine tetraester chromogen, or mixtures thereof.Type: GrantFiled: June 18, 1999Date of Patent: April 24, 2001Assignee: Xerox CorporationInventors: Clifford R. King, Donald R. Titterington, Jeffrey H. Banning
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Patent number: 6124451Abstract: A process for the preparation of substituted amido phthalocyanines having the general formula I:MPc--(CONR.sup.1 R.sup.2).sub.n Ivia the reaction of a phthalocyanine carboxamide having the formula MPc(CONH.sub.2).sub.x wherein Pc is a Phthalocyanine ring; M is a hydrogen or a metal capable of forming a metal phthalocyanine such as Mg, Al, Ni, Fe, Zn, Pb, Sn or Cu and x is a number from 0.1 to 4.0, with an amine acid salt denoted by formula II: ##STR1## wherein R.sup.1 and R.sup.2 are independently selected from the group consisting of hydrogen; an alkyl group having 1-20 carbons; a cyclic alkyl group; an aryl group; an arylalkyl having 1-20 carbons; an alcohol group having 2-20 carbons; an alkyl amino alkyl group; an aliphatic amine having 1-20 carbons; an aliphatic amine acid salt having 1-20 carbons; polyoxyalkylene groups ranging in molecular weight 89-2000; polyoxyalkyleneamines ranging in molecular weight 148-4000; Z is the hydrogen sulphate or the hydrochloride salt of the amine.Type: GrantFiled: August 17, 1999Date of Patent: September 26, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Thomas Healy, Cairan Thomas Ewins
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Patent number: 6063924Abstract: 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, diketopyrrolopyrrole or azo series, which radical A contains x N-atoms linked with B, preferably with at least one immediately adjacent or conjugated carbonyl group.B is a group of formula ##STR1## and, if x=2, 3 or 4, can also be one, two or three hydrogen atom(s), and wherein Q is a group of formula ##STR2## These soluble chromophores can be readily converted to the corresponding pigments by heating, even in the substrate into which they can be incorporated without any difficulty in dissolved form.R.sub.1 -R.sub.9 are as defined herein.Type: GrantFiled: July 22, 1996Date of Patent: May 16, 2000Assignee: Ciba Specialty Chemicals CorporationInventor: Veronique Hall-Goulle
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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: 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: 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: 5759254Abstract: The present invention provides a phthalocyanine of Formula (1): ##STR1## wherein: MPc is a phthalocyanine nucleus of Formula (2); ##STR2## in which M is a metal atom, a chloro-metal group, an oxy-metal group or hydrogenX is halogenR.sup.1 is an benzylamino or N-alkyl aminoalkylR.sup.2 is H or an optionally substituted alkyla has an average value from 15 to 8b has an average value from 1 to 8a+b is from 4 to 16.Type: GrantFiled: July 18, 1996Date of Patent: June 2, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Ian Alexander Macpherson, Iain Frank Fraser, Sharon Kathleen Wilson
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Patent number: 5618929Abstract: Substituted phthalocyanines of a formula (I) ##STR1## wherein M is a metal atom or a metal halide or oxide, or M is 2H, one H being bonded to each of the bonding N atoms (29 and 31 positions) shown, R.sub.1 to R.sub.8 are the same or different and are independently selected from C.sub.1 to C.sub.20 alkyl, C.sub.1 -C.sub.20 alkenyl, --X--COO--X.sup.1, --X--O--Y, .alpha., and --X--COZ where X is independently selected from a chemical bond, (--CH.sub.2).sub.n where n=0-20 or (CH.sub.2).sub.n --CH.dbd.CH (--CH.sub.2).sub.b where a and b are independently selected from 0-20 and a+b is in the range 0-20, X.sup.1 is independently selected from C.sub.1 -C.sub.20 alkyl or C.sub.2 -C.sub.20 alkenyl, Y is independently selected from C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.20 alkenyl or H and Z is selected from OH or NR.sup.1 R.sup.11 where R.sup.1 and R.sup.11 are independently selected from H, C.sub.1 -C.sub.20 alkyl and C.sub.2 -C.sub.Type: GrantFiled: June 7, 1995Date of Patent: April 8, 1997Assignee: The Secretary of State for Defence in Her Brittanic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Kenneth J. Harrison, Michael J. Cook, Andrew J. Thomson, Neil B. McKeown, Mervyn F. Daniel, Adrian J. Dunn
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Patent number: 5516900Abstract: A novel phthalocyanine compound having improved solubility and high purity and containing a polymerizable vinyl group within its molecule is provided. Intermediates to this phthalocyanine compound also have improved solubility and high purity. Further, with the novel phthalocyanine compound used as a starting monomer, a novel polymer is obtained which has a high content of (metal) phthalocyanine and is easy to control the orientation of phthalocyanine rings. The polymer having improved solubility and high purity is expected of use as functional material such as catalysts and recording material.Type: GrantFiled: September 14, 1994Date of Patent: May 14, 1996Assignees: Hirofusa Shirai, TDK CorporationInventors: Mutsumi Kimura, Hirofusa Shirai, Toshiki Koyama, Kenji Hanabusa, Yuichi Kubota
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Patent number: 5506708Abstract: Phthalocyanine of formula (I), wherein M is a metal or is 2H, bonded at 29 and 31 positions shown, R.sub.1 to R.sub.8 are the same or different and are independently selected from C.sub.1 to C.sub.20 alkyl, C.sub.1 -C.sub.20 alkenyl, --X--COO--X.sup.1, --X--O--Y, a, and --X--COZ where X is independently selected from a chemical bond, (CH.sub.2).sub.n where n-0-20 or (CH.sub.2).sub.a CH--CH (CH.sub.2).sub.b where a and b are independently selected from 0-20 and a+b is in the range 0-20, X.sup.1 is independently selected from C.sub.1 -C.sub.20 alkyl or C.sub.2 -C.sub.20 alkenyl, Y is independently selected from C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.20 alkenyl or H and Z is selected from OH or NR.sup.1 R.sup.11 are independently selected from H, C.sub.1 -C.sub.20 alkyl and C.sub.2 -C.sub.20 alkenyl. These phthalocyanines may exhibit discotic liquid crystal phases, absorb infra-red radiation and make good Langmuir-Blodgett films.Type: GrantFiled: July 17, 1989Date of Patent: April 9, 1996Assignee: The Secretary of State for Defence in Her Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Kenneth J. Harrison, Michael J. Cook, Andrew J. Thomson, Neil B. McKeown, Mervyn F. Daniel, Adrian J. Dunn
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Patent number: 5501710Abstract: The novel copper phthalocyanine dyestuffs of the formula (I) ##STR1## in which CuPc represents a copper phthalocyanine radical,W represents branched or straight-chain C.sub.9-16 -alkylene,a represents 2 to 4,b represents 0 to 2, andthe sum of a and b is 3 to 4,are suitable for dyeing and printing cellulose-coating materials and for producing printing inks, in particular for ink-jet printing systems.Type: GrantFiled: October 14, 1994Date of Patent: March 26, 1996Assignee: Bayer AktiengesellschaftInventor: Klaus Wunderlich
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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: 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: 5359056Abstract: A novel fluorine-containing phthalocyanine compound represented by the following formula (I): ##STR1## wherein Y is ##STR2## wherein R.sub.1 and R.sub.2 are independently a hydrogen atom or a C1-C8 alkyl group; R.sub.3 and R.sub.4 are independently a C1-C8 alkyl group; X is a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkoxyl group or a halogen atom; Z is a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkoxyl group, a C1-C4 alkoxycarbonyl group or a halogen atom; W is a C1-C4 alkoxyl group; e, f, g, h and j are independently an integer of 1 or 2; n is an integer of 1 to 8; and p and q are independently an integer of 1 to 6; a to d are an integer of 0 to 2 with the proviso that the sum of a to d is 1 to 8; and M is a non-metal, a metal, a metal oxide, a metal carbonyl or a metal halide, and further, a method of producing a fluorine-containing phthalocyanine compound represented by the above formula (I).Type: GrantFiled: July 14, 1992Date of Patent: October 25, 1994Assignee: Nippon Shokubai Co., Ltd.Inventors: Osamu Kaieda, Takashi Yodoshi, Hideki Itoh, Miho Onozaki
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Patent number: 5354857Abstract: As a new composition of matter, alkali metal or ammonium or tetraalkylammonium diazidoperfluorophthalocyanatoferrate. Other embodiments of the invention comprise compositions wherein the metal of the coordination complex is cobalt, manganese and chromium.Type: GrantFiled: July 29, 1993Date of Patent: October 11, 1994Assignee: Sun Company, Inc. (R&M)Inventors: Paul E. Ellis, Jr., James E. Lyons
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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: 5302708Abstract: Phthalocyanine dyes, in particular copper phthalocyanine and nickel phthalocyanine dyes which contain one or more groups of the formula given and defined below ##STR1## or one or more carboxy groups or both groups and which furthermore can contain one or more sulfo groups, customary sulfonamide groups and/or groups of the formula given and defined below ##STR2## dye hydroxy- and/or carboxamide-containing materials, in particular fiber materials, such as cellulose fiber materials, wool and polyamide fibers, in fast, predominantly green hues of high color strength.Type: GrantFiled: August 6, 1992Date of Patent: April 12, 1994Assignee: Hoechst AktiengesellschaftInventors: Thomas Beck, Werner H. Russ, Hartmut Springer, Marcus Banfer
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Patent number: 5296023Abstract: A colorant of Formula (1): ##STR1## wherein: L is a metal cation or hydrogen;Pc is a phthalocyanine radical having a valency from 3 to 4;R.sup.1 is H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, aralkyl or substituted aralkyl;R.sup.2 is H, alkyl, alkoxy, halo or an optionally substituted amino group;M.sup.+ is NH.sub.4.sup.+ or a substituted annonium cation; and(t+q) is from 3 to 4 inclusive;with the proviso that the group CO.sub.2 -M.sup.+ is at the 2-, 3-, 5- or 6-position in Formula (1).Type: GrantFiled: January 4, 1993Date of Patent: March 22, 1994Assignee: Zeneca LimitedInventors: Peter Gregory, Ronald W. Kenyon
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Patent number: 5250111Abstract: A pigment composition comprising a) a pigment; and b) a phthalocyanine compound having the formula I:MPc(CH.sub.2 NHCO--A).sub.n Iin which Pc represents a phthalocyanine residue which is optionally further substituted by up to an average of one chlorine or bromine atom or by a sulphonic acid group; M is hydrogen or a metal capable of forming a metal phthalocyanine; n is a number ranging from 0.1 to 4.0; and A is C.sub.3 -C.sub.21 alkenyl, C.sub.5 -C.sub.8 cycloalkyl, C.sub.7 -C.sub.11 aralkyl, C.sub.6 -C.sub.10 aryl, a 5- or 6-membered heterocyclic residue or a fused heterocyclic system.Type: GrantFiled: April 6, 1992Date of Patent: October 5, 1993Assignee: Ciba-Geigy CorporationInventors: Robert Langley, Michael D. McFarland
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Patent number: 5149800Abstract: A colorant for natural or synthetic resinous or polymeric materials, having the formula:A--[D--Z--SO.sub.2 --N(R.sub.2)--Y].sub.1-16wherein; R.sub.2 is selected from hydrogen, methyl, cyclohexyl, phenyl or Y; A is a nonionic metallophthalocyanine chromophore which can be substituted for example with halogen, alkyl, alkoxy, alkylthio, or aryloxy; Z is an arylene moiety; D is a linking group being or containing at least one of --O--, --S--, --SO.sub.2 --, --N(R.sub.3)--, or --N(SO.sub.2 R.sub.4)-- as the linking moiety, wherein R.sub.4 is unsubstituted or substituted alkyl, cycloalkyl or aryl, and R.sub.3 is R.sub.Type: GrantFiled: June 26, 1989Date of Patent: September 22, 1992Assignee: Milliken Research CorporationInventors: Edward W. Kluger, Max A. Weaver
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Patent number: 5135972Abstract: Colorants and compositions containing the same, including polymeric substrates, especially polyurethane foams which are tinted or deeper colored with the colorants which have the general formula: ##STR1## wherein R.sub.2 is selected from hydrogen or unsubstituted or substituted alkyl, cycloalkyl, aryl or Y; A is a nonionic metallophthalocyanine chromophore which can be substituted or unsubstituted; Z is an arylene moiety; each D or D' is selected from a covalent bond or a linking group consisting of or containing at least one of --O--, --S--, --N(R.sub.3)--, or --N(SO.sub.2 R.sub.4)-- as the linking moiety, wherein R.sub.4 is unsubstituted or substituted alkyl, cycloaliphatic or aryl, and R.sub.3 is R.sub.Type: GrantFiled: July 15, 1991Date of Patent: August 4, 1992Assignee: Milliken Research CorporationInventors: Edward W. Kluger, John W. Rekers, Max A. Weaver
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Patent number: 5093491Abstract: Hydrocarbons, and particularly lower molecular weight alkanes and cycloalkanes, may readily be oxidized with air or O.sub.2 to form such products as alcohols, ketones, and the like selectively on high yields when there is employed as the catalyst a highly active azide-activated metal coordination complex having the structure ##STR1## where M is a transition metal; " " is a ligand; and X is azide. The invention is also directed to certain novel azide-activated metal coordination complex catalysts per se.Type: GrantFiled: January 17, 1990Date of Patent: March 3, 1992Assignee: Sun Refining and Marketing CompanyInventors: Paul E. Ellis, Jr., James E. Lyons, Harry K. Myers, Jr.
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Patent number: 5024926Abstract: 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: October 1, 1990Date of Patent: June 18, 1991Assignees: Mitsui Toatsu Chemicals, Incorporated, Yamamoto Chemicals, IncorporatedInventors: Hisato Itoh, Katashi Enomoto, Takahisa Oguchi, Tsutomu Nishizawa
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Patent number: 5015735Abstract: A process for the preparation of a copper phthalocyanine pigment which comprises adding a dry ground mixture of crude copper phthalocyanine containing 0.1 to 20% by weight of a crystal growth inhibitor to a 50 to 90% by weight aqueous solution of sulfuric acid to obtain a sulfuric acid slurry of the dry ground mixture, adding water to the slurry to form a precipitate and recovering it to obtain pigment grade copper phthalocyanine. The copper phthalocyanine pigment prepared according to the present invention is usable in coating materials, inks or plastics.Type: GrantFiled: December 4, 1989Date of Patent: May 14, 1991Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Yusaku Ide, Koji Nakamura, Shigeki Kato
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Patent number: 4920217Abstract: The present invention provides a process for the production of dimethylaminomethyl copper phthalocyanine having an average of 1 to 4 dimethylaminomethyl groups per molecule which comprises reacting aminomethyl copper phthalocyanine having an average of 1 to 4 aminomethyl groups per molecule with formaldehyde and aqueous formic acid at a concentration of 2 to 60%, at atmospheric pressure, and at an elevated temperature.Type: GrantFiled: September 19, 1988Date of Patent: April 24, 1990Assignee: Ciba-Geigy CorporationInventors: Ian A. Lambie, Paul I. W. Yarrow, Robert Langley, Colin D. Campbell
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Patent number: 4888422Abstract: Dimethylaminomethyl copper phthalocyanine and/or its derivative represented by the general formula, ##STR1## wherein CuPc represents a copper phthalocyanine residue, X represents a hydrogen atom, a halogen atom, the group --SO.sub.3 H or the group --CH.sub.2 OH, and m and n independently represent an integer of 1 to 4,and containing only small amounts of by-products is produced by a process comprising reacting aminomethyl copper phthalocyanine and/or its derivatives represented by the general formula ##STR2## wherein CuPc, X, m and n are as defined above, with formic acid and a formaldehyde-generating substance at a temperature of 130.degree. to 150.degree. C. under a pressure of 3 to 10 kg/cm.sup.2 (gauge).Type: GrantFiled: December 5, 1988Date of Patent: December 19, 1989Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Toshio Takei, Toshio Tanaka
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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: 4784736Abstract: The preparation of a novel class of thin film membranes by interfacial polymerization is disclosed, said membanes incorporating as part of their polymeric structure the functionality of monomeric or oligomeric precursors. Specific embodiments include porphyrin and phthalocyanime derivatives that are photochemically or electrochemically active, as well as chemically asymmetric membranes.Type: GrantFiled: July 7, 1986Date of Patent: November 15, 1988Assignee: Bend Research, Inc.Inventors: Harold K. Lonsdale, Carl C. Wamser
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Patent number: 4648992Abstract: Novel phthalocyanine compounds are described, which have the formula ##STR1## in which MePc is the Si(IV)-, P(V)-, Ti(IV)-, Ge(IV)-, Cr(IV)-, Ga(III)-, Zr(IV)-, In(III)-, Sn(IV)- or Hf(IV)- phthalocyanine or -naphthalocyanine ring system, A is an anionic, nonionic or cationic group which imparts solubility in water, Z is the counter-ion to A, if the latter is an ionic group, and is 0 if A is a nonionic group, n is any desired number from 1 to 8, Y is a neutral substituent which does not impart solubility in water and p is any desired number from 0 to 6, it being possible for the groups AZ and Y present in the molecule to be identical or different in either case, and the sum of n+p being not more than 8 and MePc not being the Sn(IV)-phthalocyanine or Sn(IV)-naphthalocyanine ring system if p is 0 and if the only groups imparting water-solubility in the molecule are sulfo groups.Type: GrantFiled: February 11, 1985Date of Patent: March 10, 1987Assignee: Ciba-Geigy CorporationInventors: Gregor Graf, Gerd Holzle, Gerhard Reinert