Metal Containing Patents (Class 540/139)
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Patent number: 5932721Abstract: A phthalocyanine compound of formula (1): ##STR1## wherein FIGS. 1 to 16 around the phthalocyanine skeleton indicate the positions of carbon atoms, an oxygen atom is bonded to the carbon atom with position 1 or 4, to the carbon with position 5 or 8, to the carbon atom with position 9 or 12, and to the carbon atom with position 13 or 16, R.sup.1 is a fluorine-atom substituted alkyl group, R.sup.2 is an unsubstituted phenyl group or an alkyl-group-substituted phenyl group, R.sup.3 is an unsubstituted alkyl group, a fluorine-atom substituted alkyl group or a hydrogen atom, and M represents VO or TiO.Type: GrantFiled: March 25, 1997Date of Patent: August 3, 1999Assignee: Ricoh Company, Ltd.Inventors: Toru Yashiro, Masatoshi Taniguchi, Toshiro Narizuka
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Patent number: 5912342Abstract: The invention relates to a compound of the formula (I) wherein whereinY is the fraction of a solid or soluble support, where Y may include a residue of a functional group having been attached to said support, said functional group having been hydroxy, amino, thio, epoxy or halogen,R.sup.1 is aryl, heteroaryl, alkyl chain or ring or ring system, which may include a heteroatom, or R.sup.1 is nothing, and R.sup.2 is vinyl;CH.sub.2 CH.sub.2 X, where X is halogen; orR.sup.3 C.dbd.CHR or R.sup.3 CH--CH.sub.2 R.sup.4 X, where R.sup.3 and R.sup.4 are the same or different and are alkyl, acyl, carbonyl, cyano or nitro groups and X is halogen.The invention also relates to a method for preparation of compound (I) and to its use as a substrate in the synthesis of tertiary amines. The invention still concerns a group of alpha-2-receptor active tetrahydroisoquinoline derivatives.Type: GrantFiled: August 12, 1997Date of Patent: June 15, 1999Inventors: Petri Heinonen, Harri Lonnberg, Victor Cockcroft
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Patent number: 5912341Abstract: Porphyrazine compounds having moieties substituted at the eight peripheral .beta.-pyrrole positions are disclosed. The porphyrazine compounds have the general structural formula: ##STR1## wherein M is H.sub.2 or a metal capable of complexing with the pyrrole nitrogen atoms, and A, B, C, and D are independently selected from the group consisting of a thio moiety, an amino moiety, an oxo moiety, a phospho moiety, a seleno moiety, a telluro moiety and a noncoordinating moiety, like a hydrocarbon moiety, with the proviso that not all of A, B, C, and D are a thio moiety and that not all of A, B, C, and D are a hydrocarbon moiety. The porphyrazine compounds, depending on the identity of A, B, C, and D, are capable of complexing one to four metal ions to the periphery of the porphyrazine to form a multimetallic porphyrazine. Multimetallic porphyrazine compounds can be linked peripherally to form a linear, i.e., ribbon, polymer or a two-dimension, i.e., sheet polymer.Type: GrantFiled: September 12, 1997Date of Patent: June 15, 1999Assignee: Hoffman/Barrett, L.L.C.Inventors: Brian M. Hoffman, Anthony G.M. Barrett
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Patent number: 5889181Abstract: Disclosed herein is a selective method for the preparation of single positional isomers of monosulphonated metallo derivatives of compounds selected from the group consisting of monosulphophthalocyanines, monosulphonaphthobenzoporphyrazines and monosulphotetraphenylporphyrins.Type: GrantFiled: August 25, 1995Date of Patent: March 30, 1999Assignee: University Of SherbrookeInventors: Sveltana V. Kudrevich, Hasrat Ali, Johan E. Van Lier
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Patent number: 5883245Abstract: The present invention provides a deodorizer consisting of the water-soluble metallophthalocyanine represented by the formula: ##STR1## wherein, "Met" is a central metal, X is an acidic group or alkali metal salt thereof, m and p are respectively an integer of from 1 to 15, and m+p is not more than 16. The deodorizer shows excellent deodorizing ability for an aldehyde-origin odor.Type: GrantFiled: October 2, 1997Date of Patent: March 16, 1999Assignee: Orient Chemical Industries, Ltd.Inventors: Yasuhiro Yamasaki, Tatsuto Yamashita
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Patent number: 5880279Abstract: Cobalt dihalodihydroxydisulfophthalocyanines are useful in the extraction of low molecular weight mercaptans from petroleum (e.g., crude oil) or gas condensate.Type: GrantFiled: June 11, 1997Date of Patent: March 9, 1999Assignee: Chevron U.S.A. Inc.Inventors: Akhmet Mazgarovich Mazgarov, Azat Faridovich Vildanov, Nailya Gilmutdinovna Bazhirova, Gulnara Burkhanova Niamutdinova, Sergei Nikolaevich Sukhov
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Patent number: 5859237Abstract: A process for the production of a phthalocyanine pigment having a clear color tone, a high tinting strength and a finely milled structure by an efficient and economical process, in which the pigmentation from a phthalocyanine crude can be carried out without removing an aromatic hydrocarbon solvent used in the synthesis of the phthalocyanine crude, the process comprising thes steps of(a) reacting phthalic anhydride or its derivative, urea or its derivative and a catalyst in an organic solvent to synthesize a phthalocyanine crude,(b) wet-milling a slurry of the synthesized phthalocyanine crude in the presence of a milling medium without removing the aromatic hydrocarbon solvent, and(c) removing the organic solvent from the slurry of the milled product, purifying the milled product and drying the milled product with a spray type dryer.Type: GrantFiled: October 8, 1997Date of Patent: January 12, 1999Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Hideko Noguchi, Mikio Hayashi, Masatoshi Momose
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Patent number: 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: 5847114Abstract: The use of substituted phthalocyanines for the generation of singlet oxygen in which at least one of the peripheral carbon atoms in the 1-16 positions of the phthalocyanine nucleus (M.sub.k Pc) of Formula (1): ##STR1## wherein: M is selected from H, metal, halometal, oxymetal and hydroxymetal; andk is the inverse of 1/2 of the valency of M; is linked via an oxygen atom to an aromatic radical and the remaining peripheral carbon atoms are unsubstituted or substituted by any combination of atoms or groups and sulphonated derivatives thereof provided that the phthalocyanine absorbs electromagnetic radiation at a wavelength from 650 nm to 800 nm.Type: GrantFiled: October 25, 1995Date of Patent: December 8, 1998Assignee: Zeneca LimitedInventors: Dean Thetford, Peter Gregory
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Patent number: 5847113Abstract: A process for preparing sulfo-containing copper phthalocyanine dyes having an absorption maximum .lambda..sub.max..gtoreq.605 nm comprises heating copper phthalocyanine with at least 15% strength oleum at about 50.degree.-110.degree. C. until the reaction product has a .lambda..sub.max..gtoreq.605 nm, then diluting the resulting sulfonation product with water, adding a tertiary, lipophilic amine and stirring at elevated temperature until the lipophilic phase comprising the ammonium salt separates from the aqueous sulfuric acid phase, subsequently admixing the lipophilic phase, optionally after washing with water, with a water-soluble base whose sulfonate salt is to be prepared and water, separating the resulting phases and leaving the salt in the aqueous solution or isolating it therefrom.The products are especially useful for dyeing cellulosic fibers or polyamides.Type: GrantFiled: October 10, 1997Date of Patent: December 8, 1998Assignee: BASF AktiengesellschaftInventor: Rudolf Bermes
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Patent number: 5834608Abstract: Copper phthalocyanine is prepared by heating and reacting phthalic acid or a derivative thereof, urea or a derivative thereof and copper or a copper compound in the presence of molybdenum or a molybdenum compound as a catalyst and sulfur.Type: GrantFiled: May 30, 1996Date of Patent: November 10, 1998Assignee: Kawasaki Kasei Chemicals Ltd.Inventor: Kazuhiro Maruyama
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Patent number: 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: 5817804Abstract: Mixtures of isomeric substituted phthalocyanines, and process for their preparation Mixtures of four .alpha.-alkoxy-substituted phthalocyanine isomers, predominantly ##STR1## or of four .beta.-alkoxy-substituted phthalocyanine isomers, whereMe is a divalent metal atom or a divalent oxo metal,R.sub.1 is a linear or branched C.sub.1 --C.sub.16 alkyl, C.sub.3 --C.sub.16 alkenyl or C.sub.3 --C.sub.16 alkynyl radical which is unsubstituted or substituted by C.sub.1 --C.sub.12 alkoxy, --CN, NO.sub.2, halogen, --OH, phenyl, cyanophenyl, nitrophenyl, halophenyl, hydroxyphenyl or (C.sub.1 --C.sub.12 alkoxy)phenyl,wherein two isomers of the formula II and of the formula III make up at least 80% of the total mixture and the two other isomers make up at most 20% of the total mixture, with the ratio between the compounds of the formula II and the compounds of the formula III being from 0.3 to 3.0: 1.The isomer mixtures can be obtained by reacting .alpha.- or .beta.Type: GrantFiled: April 23, 1997Date of Patent: October 6, 1998Assignee: Ciba Specialty Chemicals CorporationInventor: Heinz Wolleb
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Patent number: 5817154Abstract: 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.Type: GrantFiled: August 29, 1995Date of Patent: October 6, 1998Assignee: Zeneca LimitedInventors: Peter Gregory, Stephen James Reynolds, Raymond Lesley White
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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: 5788914Abstract: A near infrared ray absorbing compound having an improved solubility and light resistance can be obtained by amidating and/or imidating the amino groups on substituents of a phthalocyanine. According to its preparation process, the desired near infrared ray absorbing compound can be easily prepared by reacting the phthalocyanine having an elimination group such as a halogen atom with a 2-aminothiophenol derivative, and then amidating and/or imidating a part or all of the remaining primary or secondary amino groups. Moreover, substituents on the benzene rings of the phthalocyanine can be coordinated with metals, whereby an absorption wavelength can be broadened and the near infrared rays in a long wave range can be absorbed. The near infrared ray absorbing compound of the present invention is useful as a heat ray absorbing material.Type: GrantFiled: September 26, 1996Date of Patent: August 4, 1998Assignees: Mitsui Chemicals, Inc., Yamamoto Chemicals, Inc.Inventors: Ryu Oi, Kazuhiro Seino, Yuko Mochizuki, Keisuke Takuma
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Patent number: 5776576Abstract: A novel phthalocyanine compound having improved solubility and high purity and containing a polymerizable vinyl group within its molecule is provided. Intermediates to this phthalocyanine compound also have improved solubility and high purity. Further, with the novel phthalocyanine compound used as a starting monomer, a novel polymer is obtained which has a high content of (metal) phthalocyanine and is easy to control the orientation of phthalocyanine rings. The polymer having improved solubility and high purity is expected of use as functional material such as catalysts and recording material.Type: GrantFiled: October 7, 1996Date of Patent: July 7, 1998Assignees: Hirofusa Shirai, TDK CorporationInventors: Mutsumi Kimura, Hirofusa Shirai, Toshiki Koyama, Kenji Hanabusa, Yuichi Kubota
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Patent number: 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: 5756247Abstract: Hydroxygallium phthalocyanine crystals having intense diffraction peaks at Bragg angles (2.theta..+-.0.2.degree.) of 7.5.degree., 9.9.degree., 12.5.degree., 16.3.degree., 18.6.degree., 25.1.degree. and 28.3.degree. in Cuk.alpha. characteristic X-ray diffractometry, a process for producing the same, and an electrophotographic photoreceptor containing the same are disclosed. The hydroxygallium phthalocyanine crystals are obtained by once preparing impurity-free hydroxygallium phthalocyanine having intense X-ray diffraction peaks at specific Bragg angles, followed by a solvent treatment for crystal transformation, in which the impurity-free crystals are prepared by using excess phthalocyanine ring-forming compound in the synthesis of starting gallium phthalocyanine or by removing insoluble matter from the acid paste of starting gallium phthalocyanine.Type: GrantFiled: May 23, 1997Date of Patent: May 26, 1998Assignee: Fuji Xerox Co., Ltd.Inventors: Fumiaki Tambo, Katsumi Daimon, Yasuo Sakaguchi, Kazuo Yamasaki
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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: 5705101Abstract: A phthalocyanine near infrared absorber having a broad absorption range in the near infrared region and represented by the following formula (1): ##STR1## wherein each of the groups is defined.Type: GrantFiled: December 18, 1995Date of Patent: January 6, 1998Assignees: Mitsui Toatsu Chemicals, Inc., Yamamoto Chemicals Inc.Inventors: Ryu Oi, Kazuhiro Seino, Keisuke Takuma
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Patent number: 5675001Abstract: Porphyrazine compounds having moieties substituted at the eight peripheral .beta.-pyrrole positions are disclosed. The porphyrazine compounds have the general structural formula: ##STR1## wherein M is H.sub.2 or a metal capable of complexing with the pyrrole nitrogen atoms, and A, B, C and D are independently selected from the group consisting of a thio moiety, an amino moiety, an oxo moiety, a phospho moiety, a seleno moiety, a telluro moiety and a non-coordinating moiety, like a hydrocarbon moiety, with the proviso that not all of A, B, C and D are a thio moiety and that not all of A, B, C, and D are a hydrocarbon moiety. The porphyrazine compounds, depending on the identity of A, B, C and D, are capable of complexing one to four metal ions to the periphery of the porphyrazine to form a multimetallic porphyrazine. Multimetallic porphyrazine compounds can be linked by the peripherally-complexed metal ions to form a linear, i.e., ribbon, polymer or a two-dimension, i.e., sheet polymer.Type: GrantFiled: March 14, 1995Date of Patent: October 7, 1997Assignee: Hoffman/Barrett, L.L.C.Inventors: Brian M. Hoffman, Anthony G. M. Barrett
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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: 5665875Abstract: Tetraazaporphins represented by the general formula (I): ##STR1## provide substances derived from organisms (e.g. antigens, antibodies, nucleotides, etc.) which have been labeled with a fluorochrome for labeling comprising the tetraazaporphin; reagents comprising any of the labeled substances which can be utilized for assay of various antigens, drugs, DNAs and the like; and analysis of the base sequence of DNA. Fluorescence analysis can be carried out using the labeled substances.Type: GrantFiled: June 5, 1995Date of Patent: September 9, 1997Assignee: Hitachi Chemical Co., Ltd.Inventors: Seiji Tai, Mitsuo Katayose, Hiroo Watanabe
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Patent number: 5663327Abstract: Hydroxygallium phthalocyanine crystals having intense diffraction peaks at Bragg angles (2.theta..+-.0.2.degree.) of 7.5.degree., 9.9.degree., 12.5.degree., 16.3.degree., 18.6.degree., 25.1.degree. and 28.3.degree. in CuK.alpha. characteristic X-ray diffractometry, a process for producing the same, and an electrophotographic photoreceptor containing the same are disclosed. The hydroxygallium phthalocyanine crystals are obtained by once preparing impurity-free hydroxygallium phthalocyanine having intense X-ray diffraction peaks at specific Bragg angles, followed by a solvent treatment for crystal transformation, in which the impurity-free crystals are prepared by using excess phthalocyanine ring-forming compound in the synthesis of starting gallium phthalocyanine or by removing insoluble matter from the acid paste of starting gallium phthalocyanine.Type: GrantFiled: September 29, 1995Date of Patent: September 2, 1997Assignee: Fuji Xerox Co., Ltd.Inventors: Fumiaki Tambo, Katsumi Daimon, Yasuo Sakaguchi, Kazuo Yamasaki
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Patent number: 5663326Abstract: Mixtures of four .alpha.-alkoxy-substituted phthalocyanine isomers, predominantly ##STR1## or of four .beta.-alkoxy-substituted phthalocyanine isomers, whereMe is a divalent metal atom or a divalent oxo metal,R.sub.1 is a linear or branched C.sub.1 -C.sub.16 alkyl, C.sub.3 -C.sub.16 alkenyl or C.sub.3 -C.sub.16 alkynyl radical which is unsubstituted or substituted by C.sub.1 -C.sub.12 alkoxy, --CN, NO.sub.2, halogen, --OH, phenyl, cyanophenyl, nitrophenyl, halophenyl, hydroxyphenyl or (C.sub.1 -C.sub.12 alkoxy)phenyl,wherein two isomers of the formula II and of the formula III make up at least 80% of the total mixture and the two other isomers make up at most 20% of the total mixture, with the ratio between the compounds of the formula II and the compounds of the formula III being from 0.3 to 3.0:1.The isomer mixtures can be obtained by reacting .alpha.- or .beta.Type: GrantFiled: September 18, 1995Date of Patent: September 2, 1997Assignee: Ciba-Geigy CorporationInventor: Heinz Wolleb
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Patent number: 5656752Abstract: A process is described for preparing alkoxy-octasubstituted metal-free or metal-containing naphthalocyanines by etherification of 1,4-dihydroxy-2,3-dicyanonaphthalene and formation of the metal-free naphthalocyanine with or without subsequent metallization.Type: GrantFiled: September 28, 1995Date of Patent: August 12, 1997Assignee: BASF AktiengesellschaftInventors: Juergen Kipper, Bernhard Albert
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Patent number: 5646274Abstract: A phthalocyanine monoazo compound which is represented by the following formula (I): ##STR1## wherein the variable radicals have the meaning given in the description, and the phthalocyanine monoazo compound has green color.Type: GrantFiled: October 30, 1995Date of Patent: July 8, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Toshiyuki Araki, Takemi Tokieda, Shin-ichi Yabushita, Yasuyoshi Ueda, Bunzi Tsukise
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Patent number: 5633370Abstract: Novel naphthalocyanine compounds are provided including nitro- and amino-substituted naphthalocyanine compounds, and vinyl-containing naphthalocyanine compounds. The compounds have improved solubility and high purity and are expected to find use as photo-functional materials such as dyes. Polymers are obtained using the vinyl-containing naphthalocyanine compounds- The polymers also have improved solubility, high purity, a high naphthalocyanine content and ease of control of the orientation of naphthalocyanine rings and are expected of use as various functional materials.Type: GrantFiled: October 21, 1994Date of Patent: May 27, 1997Assignees: Hirofusa Shirai, TDK CorporationInventors: Hirofusa Shirai, Mutsumi Kimura, Yuichi Kubota
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Patent number: 5629418Abstract: Titanyl fluorophthalocyanines, and electrophotographic elements, and a method for preparing titanyl fluorophthalocyanine having the steps of: dissolving titanyl fluorophthalocyanine in acid to form a solution; admixing the solution and water to precipitate out amorphous titanyl fluorophthalocyanine; washing the amorphous titanyl fluorophthalocyanine until substantially all of the acid is removed; and retaining the amorphous titanyl fluorophthalocyanine under ambient conditions of wetness/dryness and temperature exclusive of conditions combining both dryness and a temperature of greater than about 50.degree. C.Type: GrantFiled: October 27, 1994Date of Patent: May 13, 1997Assignee: Eastman Kodak CompanyInventors: Michel F. Molaire, Jeanne E. Kaeding, William T. Gruenbaum
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Patent number: 5629417Abstract: A phthalocyanine of Formula (1): ##STR1## wherein: M.sub.k PC is a phthalocyanine nucleus of Formula (2): ##STR2## M is a metal atom, a chloro-metal group, and oxy-metal group or hydrogen; k is inverse of 1/2 valency of M; R and R.sup.1 each independently is an organic radical;R.sup.2 is H or optionally substituted alkyl;a is an average value from 15 to 8;b is an average value from 1 to 8; anda+b is from 15 to 16; and sulphonated derivatives thereof and process for their preparation.The phthalocyanines of the present invention are useful for absorbing electro-magnetic radiation from for example a laser source and may be used in a coating for optical data storage disks, or in security applications such as printing banknotes or cheques, or in the preparation of lithographic printing plates or in washing powders to assist in bleaching.Type: GrantFiled: January 31, 1996Date of Patent: May 13, 1997Assignee: Zeneca LimitedInventors: James S. Campbell, Peter Gregory, Dean Thetford
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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: 5618930Abstract: A novel phthalocyanine compound having improved solubility and high purity and containing a polymerizable vinyl group within its molecule is provided. Intermediates to this phthalocyanine compound also have improved solubility and high purity. Further, with the novel phthalocyanine compound used as a starting monomer, a novel polymer is obtained which has a high content of (metal) phthalocyanine and is easy to control the orientation of phthalocyanine rings. The polymer having improved solubility and high purity is expected of use as functional material such as catalysts and recording material.Type: GrantFiled: March 1, 1996Date of Patent: April 8, 1997Assignees: Hirofusa Shirai, TDK CorporationInventors: Mutsumi Kimura, Hirofusa Shirai, Toshiki Koyama, Kenji Hanabusa, Yuichi Kubota
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Patent number: 5608112Abstract: Nitrogen-containing substituents of aliphatic or aromatic compounds can be reduced by treatment with a reagent comprising (i) at least one complex of a transition metal of group 4 or 5 with a multidentate or unidentate organic or inorganic ligand and (ii) a reducing agent. The reaction is conducted optionally in the presence of an aliphatic or aromatic amine, and/or in the presence of an inert organic solvent.Type: GrantFiled: July 10, 1995Date of Patent: March 4, 1997Assignee: The Trustees of Princeton UniversityInventor: Jeffrey Schwartz
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Patent number: 5608053Abstract: The use of substituted phthalocyanines for the generation of singlet oxygen in which at least one of the peripheral carbon atoms in the 1-16 positions of the phthalocyanine nucleus (M.sub.k Pc) of Formula (1): ##STR1## wherein: M is selected from H, metal, halometal, oxymetal and hydroxymetal; andk is the inverse of 1/2 of the valency of M;is linked via an oxygen atom to an aromatic radical and the remaining peripheral carbon atoms are unsubstituted or substituted by any combination of atoms or groups and sulphonated derivatives thereof provided that the phthalocyanine absorbs electromagnetic radiation at a wavelength from 650 nm to 800 nm.Type: GrantFiled: October 25, 1995Date of Patent: March 4, 1997Assignee: Zeneca LimitedInventors: Dean Thetford, Peter Gregory
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Patent number: 5602249Abstract: A process for the production of a copper phthalocyanine by a urea method, which enables the production of a highly pure copper phthalocyanine and/or its derivative by a uniform reaction, i.e., is free from problems of an insufficient mixing, nonuniformity in heat transfer and adhesion of the reaction mixture to a reactor wall, the process comprising heating a raw material mixture containing a phthalic acid, a nitrogen source, a copper compound and a catalyst in an inert solvent, the process being carried out in the presence of a surfactant which enables the raw material mixture and a reaction product to be dispersed in the inert solvent while the raw materials are being reacted and which can be removed or deactivated by hydrolysis with an acid or an alkali at a step of purifying the reaction product or forming the reaction product into a pigment after the reaction.Type: GrantFiled: March 29, 1995Date of Patent: February 11, 1997Assignee: Toyo Ink Manufacturing Co., Ltd.Inventor: Michichika Hikosaka
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Patent number: 5585483Abstract: Phthalonitrile, an alkali metal or an alkali metal compound, and a hydrogen donor compound are heated in an organic solvent to synthesize a partially hydrogenated alkali metal phthalocyanine, which is then brought into contact with a dealkalizing agent to effect substitution with hydrogen of the partially hydrogenated alkali metal phthalocyanine to thereby obtain high-purity metal-free phthalocyanine. FX-type metal-free phthalocyanine as obtained according to the foregoing procedure may be used as a charge-generating substance to produce an electrophotographic photoconductor of high image quality which is highly sensitive to near infrared rays.Type: GrantFiled: October 20, 1995Date of Patent: December 17, 1996Assignee: Fuji Electric., Ltd.Inventors: Shinichi Tamura, Seishi Terasaki, Tadashi Mimura, Teruaki Kobayashi, Youichi Tei
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Patent number: 5582774Abstract: 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: February 26, 1991Date of Patent: December 10, 1996Assignees: Mitsui Toatsu Chemicals, Incorporated, Yamamoto Chemicals, IncorporatedInventors: Hisato Itoh, Katashi Enomoto, Takahisa Oguchi, Tsutomu Nishizawa
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Patent number: 5563261Abstract: A process for the preparation of hydroxygallium phthalocyanines which comprises hydrolyzing a gallium phthalocyanine precursor pigment by dissolving said hydroxygallium phthalocyanine in a strong acid and then reprecipitating the resulting dissolved pigment in basic aqueous media; removing any ionic species formed by washing with water, concentrating the resulting aqueous slurry comprised of water and hydroxygallium phthalocyanine to a wet cake; removing water from said slurry by azeotropic distillation with an organic solvent, and subjecting said resulting pigment slurry to mixing with the addition of a second solvent to cause the formation of said hydroxygallium phthalocyanine polymorphs.Type: GrantFiled: June 6, 1995Date of Patent: October 8, 1996Assignee: Xerox CorporationInventors: Barkev Keoshkerian, George Liebermann, Cheng-Kuo Hsiao, James D. Mayo, Dasarao Murti, Sandra J. Gardner
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Patent number: 5556967Abstract: Hydroxygallium phthalocyanine crystals are produced by reacting a gallium trihalide with phthalonitrile or diiminoisoindoline in a halogenated aromatic hydrocarbon solvent, treating the resulting halogenated gallium phthalocyanine with an amide solvent, and hydrolyzing the halogenated gallium phthalocyanine. The photoreceptor exhibits stabilized electrophotographic characteristics.Type: GrantFiled: October 14, 1994Date of Patent: September 17, 1996Assignee: Fuji Xerox Co., Ltd.Inventors: Katsumi Nukada, Katsumi Daimon, Yasuo Sakaguchi, Masakazu Iijima
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Patent number: 5556966Abstract: A process for the production of an aluminum phthalocyanine composition or a halogenated aluminum phthalocyanine composition in high yield and purity is provided which entails bringing a molten salt of aluminum chloride and/or aluminum bromide and a phthalocyanine compound having a central element other than aluminum into contact with each other in a predetermined temperature range thereby to substitute aluminum for the central element. Alternatively, the process involves conducting the aforementioned step, and introducing a halogen into the resultant reaction mixture.Type: GrantFiled: July 19, 1994Date of Patent: September 17, 1996Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Shuuichi Kimura, Michichika Hikosaka, Masami Shirao, Akimitsu Mochizuki, Junichi Tsuchida
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Patent number: 5545733Abstract: A method for preparing hydroxygallium phthalocyanine crystals wherein hydroxygallium phthalocyanine crystals having distinct diffraction peaks at 7.0.degree., 13.4.degree., 16.6.degree., 26.0.degree. and 26.7.degree. of the Bragg angle (2.theta..+-.0.2.degree.) with respect to CuK.alpha. characteristics X-ray in the X-ray diffraction spectrum are crystal-transferred by solvent treatment. The crystals after crystal-transfer have distinct diffraction peaks at (i) 7.7.degree., 16.5.degree., 25.1.degree. and 26.6.degree., (ii) 7.9.degree., 16.5.degree., 24.4.degree. and 27.6.degree., (iii) 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, (iv) 7.5.degree., 9.9.degree., 12.5.degree., 16.3.degree., 18.6.degree., 25.1.degree. and 28.8.degree. or (v) 6.8.degree., 12.8.degree., 15.8.degree. and 26.0.degree. of the Bragg angle (2.theta..+-.0.2.degree. C.) with respect to CuK.alpha. characteristics X-ray in the X-ray diffraction spectrum.Type: GrantFiled: August 10, 1994Date of Patent: August 13, 1996Assignee: Fuji Xerox Co., Ltd.Inventors: Katsumi Daimon, Katsumi Nukada, Yasuo Sakaguchi, Ryosaku Igarashi
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Patent number: 5521306Abstract: A process for the preparation of Type V hydroxygallium phthalocyanine which comprises the in situ formation of an alkoxy-bridged gallium phthalocyanine dimer, hydrolyzing said alkoxy-bridged gallium phthalocyanine dimer to hydroxygallium phthalocyanine, and subsequently converting the hydroxygallium phthalocyanine product obtained to Type V hydroxygallium phthalocyanine.Type: GrantFiled: April 26, 1994Date of Patent: May 28, 1996Assignee: Xerox CorporationInventors: Richard A. Burt, Cheng-Kuo Hsiao, Dasarao Murti, Roger E. Gaynor, Barkev Keoshkerian, James D. Mayo, George Liebermann
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Patent number: 5516899Abstract: A phthalocyanine of Formula (1): ##STR1## wherein: M.sub.k PC iS a phthalocyanine nucleus of Formula (2): ##STR2## M is a metal atom, a chloro-metal group, and oxy-metal group or hydrogen; k is inverse of 1/2 valency of M;R and R.sup.1 each independently is an organic radical;R.sup.2 is H or optionally substituted alkyl;a is an average value from 15 to 8;b is an average value from 1 to 8; anda+b is from 15 to 16; and sulphonated derivatives thereof and process for their preparation.The phthalocyanines of the present invention are useful for absorbing electro-magnetic radiation from for example a laser source and may be used in a coating for optical data storage disks, or in security applications such as printing banknotes or checks, or in the preparation of lithographic printing plates or in washing powders to assist in bleaching.Type: GrantFiled: July 20, 1994Date of Patent: May 14, 1996Assignee: Zeneca LimitedInventors: James S. Campbell, Peter Gregory, Dean Thetford
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Patent number: 5508395Abstract: A hydroxygallium phthalocyanine crystal, having distinct diffraction peaks at Bragg angles (2.theta.+/-0.2.degree.) of 7.0.degree., 13.4.degree., 16.6.degree., 26.0.degree. and 26.7.degree. to CuK.alpha. characteristic X-ray-in X-ray diffraction spectrum; a process for preparing the hydroxygallium phthalocyanine crystal; and a electrophotographic photoreceptor comprising the hydroxygallium phthalocyanine crystal.Type: GrantFiled: March 25, 1994Date of Patent: April 16, 1996Assignee: Fuji Xerox Co., Ltd.Inventors: Katsumi Daimon, Katsumi Nukada, Yasuo Sakaguchi, Ryosaku Igarashi
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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: 5496378Abstract: Basic dyes of the formula ##STR1## where n is from 1 to 3,CuPc is a copper phthalocyanine radical,R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl,R.sup.2 is C.sub.1 -C.sub.4 -alkyl,R.sup.3 is hydrogen or C.sub.1 -C.sub.4 -alkyl,R.sup.4 is C.sub.1 -C.sub.4 -alkyl andAn.sup..crclbar. is the equivalent of an anion,with the proviso that R.sup.1 and R.sup.3 are not both hydrogen, are useful for dyeing or printing polymeric material.Type: GrantFiled: September 12, 1994Date of Patent: March 5, 1996Assignee: BASF AktiengesellschaftInventors: Heidi Hengelsberg, Manfred Ruske, Udo Mayer
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Patent number: 5496939Abstract: A method for producing copper phthalocyanine, which comprises heating and reacting phthalic acid or a phthalic acid derivative, urea or a urea derivative, and a copper compound, using molybdenum or a molybdenum compound as a catalyst, in the presence or absence of an inert organic solvent, wherein at least one compound selected from the group consisting of an aromatic dithiol compound of the following formula (I), a saturated aliphatic dithiol compound of the following formula (II), and their precursors, or at least one compound selected from the group consisting of a ruthenium compound and an osmium compound, is added to the reaction system: ##STR1##C.sub.m H.sub.2m-x R.sub.x (SH).sub.2 (II)wherein ring A in the formula (I) is a 6-membered single carbon ring or polycyclic condensed carbon ring aromatic compound, R for R.sub.n in the formula (I) or for R.sub.Type: GrantFiled: March 8, 1995Date of Patent: March 5, 1996Assignee: Kawasaki Kasei Chemicals Ltd.Inventor: Kazuhiro Maruyama
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Patent number: 5495011Abstract: A process for preparing hydroxygallium phthalocyanine comprising reacting a gallium trialkoxide and phthalonitrile or diiminoisoindoline in an alcohol solvent, preferably an alcohol having a boiling point of not lower than 150.degree. C., such as ethylene glycol, and hydrolyzing the resulting gallium phthalocyanine, preferably in an aqueous solution of an acid, such as sulfuric acid. The resulting hydroxygallium phthalocyanine exhibits stable electrophotographic characteristics, particularly photosensitivity, charging properties, and a dark decay rate.Type: GrantFiled: August 19, 1993Date of Patent: February 27, 1996Assignee: Fuji Xerox Co., Ltd.Inventors: Katsumi Nukada, Katsumi Daimon, Masakazu Iijima, Yasuo Sakaguchi