Phthalocyanines Patents (Class 540/122)
  • Patent number: 6043355
    Abstract: A phthalocyanine compound of formula (I): ##STR1## wherein FIGS. 1 to 16 around the phthalocyanine skeleton indicate the positions of carbon atoms in each benzene ring thereof; an oxygen atom is bonded to the carbon atom with position 1 or 4, to the carbon atom 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 Zn, Cu or Ni.
    Type: Grant
    Filed: February 5, 1998
    Date of Patent: March 28, 2000
    Assignees: Ricoh Company, Ltd., Yamada Chemical Co., Ltd.
    Inventors: Toru Yashiro, Masatoshi Taniguchi, Toshiro Narizuka, Hiroaki Tomita
  • Patent number: 6034236
    Abstract: A method for producing a novel phthalocyanine compound which excels in yield and purity, allows no introduction of a chlorine atom into the phthalocyanine skeleton, and possesses relatively bulky substituents is provided. This method is characterized by causing an orthophthalonitrile compound having a substituent exhibiting smaller .sigma..sub.p values than .sigma..sub.m values in the Hammett's rule to react with a metal oxide in the presence of a compound forming in the aqueous solution thereof at 25.degree. C. an acid or conjugate acid having a dissociation index pKa (the logarithmic value of the reciprocal of the dissociation constant of the acid or conjugate acid) of not more than 7.0.
    Type: Grant
    Filed: June 5, 1998
    Date of Patent: March 7, 2000
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Minoru Aoki, Osamu Kaieda
  • Patent number: 6025486
    Abstract: A compound of formula (1) and salts thereof, wherein: M is a metal or hydrogen; Pc is a phthalocyanine nucleus; each R.sup.1 independently is H or optionally substituted alkyl aryl or aralkyl; each L.sup.1 independently is a divalent organic linking group; Z is an optionally substituted piperazinyl group; q is 1 or 2; x and y each independently have a value of 0.5 to 3.5; and (x+y) is from 2 to 5. A process for making the compounds of formula (1). The compounds of formula (1) are useful as colorants for inks which are used in for example ink jet printing of substrates such as paper, plastics, textile materials, metal or glass.
    Type: Grant
    Filed: April 7, 1998
    Date of Patent: February 15, 2000
    Assignee: Zeneca Limited
    Inventors: Prahalad Manibhai Mistry, Ronald Wynford Kenyon
  • Patent number: 6015896
    Abstract: A compound of formula (1) and salts thereof, wherein: M is a metal or hydrogen; Pc is phthalocyanine nucleus; R.sup.1, R.sup.2, W.sup.1 and W.sup.2 are each independently H or optionally substituted alkyl, aryl or aralkyl; R.sup.3 is an aminoalkyl group; L is a divalent organic linking group; x, y and t are each independently 0.5 to 2.5; and (x+y+t) is from 3 to 4. A process for making the compounds of formula (1). The compounds of formula (1) are useful as colorants for inks which are used in for example ink jet printing of substrates such as paper, plastics, textile materials, metal or glass.
    Type: Grant
    Filed: April 7, 1998
    Date of Patent: January 18, 2000
    Assignee: Zeneca Limited
    Inventors: Prahalad Manibhai Mistry, Ronald Wynford Kenyon
  • Patent number: 6013777
    Abstract: 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: Grant
    Filed: June 10, 1998
    Date of Patent: January 11, 2000
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Zhimin Hao, John S. Zambounis, Abul Iqbal
  • Patent number: 6008346
    Abstract: The present invention provides an electrophotographic photoreceptor which can be prepared so easily as to exhibit a photosensitivity well-adjusted for the respective type of machine in the dip coating method, which is an ordinary method for the preparation of an electrophotographic photoreceptor. A novel electrophotographic photoreceptor is provided comprising a charge-transporting layer and a charge-generating layer provided on an electrically-conductive support, wherein the charge-generating layer is a layer comprising a charge-generating material containing a phthalocyanine compound represented by the following general formula (1) dispersed in a resin: ##STR1## wherein Ar.sup.1 and Ar.sup.2 each independently represent an orthophenylene group which may have a substituent; and Pc represents an unsubstituted or substituted phthalocyanine residue.
    Type: Grant
    Filed: April 30, 1999
    Date of Patent: December 28, 1999
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Yoshitaka Saito, Katsunori Oba, Shinichi Okada
  • Patent number: 6004530
    Abstract: The present invention refers to a process for the preparation of an activated metallo-porphyrin derivative and to novel activated metallo-porphyrin derivatives obtainable by said process. Further, the present invention refers to conjugates of metallo-porphyrins with molecules having at least one primary amino group, especially biomolecules. The conjugates are used in a procedure for the detection of a biological substance, especially in an immunoassay or a nucleic acid hybridization assay.
    Type: Grant
    Filed: May 30, 1997
    Date of Patent: December 21, 1999
    Assignee: Roche Diagnostics GmbH
    Inventors: Gregor Sagner, Richard Robert De Haas, Rob Van Gijlswijk, Hans Tanke
  • Patent number: 5998609
    Abstract: A phthalocyanine compound of a structural formula of phthalocyanine represented by the general formula (1): ##STR1## wherein 1 to 8 of a total 16 positions are substituted with a phenoxy group, the phenoxy group at either of the ortho positions is substituted with an aryl group which may be substituted, all the atoms in the aryl group and the substituents at the residual ortho positions excluding the hydrogen atoms assume a total atomic radius of not less than 6.0 .ANG., and a central atom group M contains a metal atom of not less than trivalence, a bromine-substituent of the compound, a phthalocyanine composition comprising the phthalocyanine compound and the bromine atom-containing phthalocyanine compound, and an optical recording medium containing it in a recording layer.
    Type: Grant
    Filed: June 12, 1998
    Date of Patent: December 7, 1999
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Minoru Aoki, Osamu Kaieda, Kiyoshi Masuda, Yasunori Okumura
  • Patent number: 5973140
    Abstract: The invention relates to a novel phthalocyanine compound absorbing in the near infrared region of the spectrum with a high absorption coefficient which features high solubility in solvents, good compatibility with resins and high aging resistance, thus finding application as a near infrared ray absorbing material or a light-heat conversion material with great advantage and to a process for producing the phthalocyanine compound. The novel phthalocyanine compound has the following general formula: ##STR1## wherein R represents alkyl or alkoxyalkyl; X represents halogen, alkylthio, phenylthio which may be substituted, or naphthylthio which may be substituted; M represents a couple of hydrogen atoms, a divalent metal, or a trivalent or tetravalent metal derivative. The near infrared ray absorbing and light-heat conversion materials containing the above phthalocyanine compound are also described.
    Type: Grant
    Filed: December 28, 1998
    Date of Patent: October 26, 1999
    Assignees: Yamamoto Chemicals, Inc, Mitsui Chemicals Inc.
    Inventors: Yojiro Kumagae, Toshihiro Masaoka, Shigeo Fujita, Tsunehito Eda
  • Patent number: 5942612
    Abstract: Phthalocyanines of formula (I) are described wherein M is a metal atom, metal compound or is 2H; one H being bonded to each of the two nitrogen atoms depicted as being bonded to M (positions 29 and 31 shown); R.sub.1 -R.sub.25 may be the same or different and are chosen independently from the following groups: straight or branched chain alkyl containing up to 32 carbon atoms where 1 or more non-adjacent CH.sub.2 groups may be replaced by O and/or a double bond; H; F; and at least one of R.sub.2.3.9.10.16.17.34.24 is chosen from formula (II) wherein Y, X and Z are chosen independently from HO, `O, --O, OR, H, C.sub.1-16 branched or straight chain alkyl or alkoxy; X and Z may also be selected from phenyl groups which may be, independently of each other, substituted with one or more C.sub.1-5 straight or branched chain alkyl groups; R may be C.sub.1-16 branched or straight chain alkyl or alkene wherein 1 or more non-adjacent CH.sub.
    Type: Grant
    Filed: June 20, 1997
    Date of Patent: August 24, 1999
    Assignee: Secretary of State for Defence in her Britannic Majesty's Government of the U.K. of Gt. Britain and N. Ireland Defence Evaluation & Research Agency
    Inventors: Neil Bruce McKeown, Guy James Clarkson, Paul Humberstone
  • Patent number: 5932722
    Abstract: An electrophotographic photosensitive member having a high sensitivity to long-wavelength light as emitted by a semiconductor laser and causing little change in potential change during repetitive use is formed by using as a charge-generating material a hydroxygallium phthalocyanine having a crystal form characterized by a strongest peak at a Bragg angle (2.theta..+-.0.2 deg.) of 28.1 deg. in a CuK.sub..alpha. characteristic X-ray diffraction pattern. The hydroxygallium phthalocyanine may preferably be produced through a process including treating a halogenated gallium phthalocyanine for conversion into a hydrous hydroxygallium phthalocyanine, freeze-drying the hydrous hydroxygallium phthalocyanine into a low-crystallinity hydroxygallium phthalocyanine, and milling the low-crystallinity hydroxygallium phthalocyanine.
    Type: Grant
    Filed: January 8, 1999
    Date of Patent: August 3, 1999
    Assignee: Canon Kabushiki Kaisha
    Inventors: Katsuaki Hirai, Noriyoshi Ueda, Yoshifumi Takehara, Masaaki Sato, Katsuhito Kato, Naho Saitoh, Kenichi Hayashi
  • Patent number: 5932721
    Abstract: 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: Grant
    Filed: March 25, 1997
    Date of Patent: August 3, 1999
    Assignee: Ricoh Company, Ltd.
    Inventors: Toru Yashiro, Masatoshi Taniguchi, Toshiro Narizuka
  • Patent number: 5932723
    Abstract: A process for preparing metal-free phthalocyanine by reductive cyclization of phthalonitrile in the presence of an aliphatic alcohol, of a redox catalyst and of an inorganic base comprises effecting the cyclization in the presence of one or more phthalocyanine derivatives selected from the group consisting of phthalocyanine-sulfonic acids and -carboxylic acids and their alkali metal, ammonium and alkylarnozium salts, the amino-substituted and aminomethylated phthalocyanines and their reaction products with alkylating agents, sulfonic acids, sulfonyl chlorides and carbonyl chlorides, the imidomethylene- and amidomethylene-substituted phthalocyanines, the alkyl-, aryl- and cyano-substituted phthalocyanines, the hydroxyl- and alkoxy-substituted phthalocyanines and their reaction products with tetraalkyl- and tetraalkoxy-silanes and the halogenated phthalocyanines.
    Type: Grant
    Filed: December 16, 1997
    Date of Patent: August 3, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Andrea Birgit Schutze, Frank Scherhag, Ingo Klopp, Anette Hartmann
  • Patent number: 5916481
    Abstract: 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: Grant
    Filed: June 18, 1996
    Date of Patent: June 29, 1999
    Assignee: The Procter & Gamble Company
    Inventor: Alan David Willey
  • Patent number: 5912341
    Abstract: 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: Grant
    Filed: September 12, 1997
    Date of Patent: June 15, 1999
    Assignee: Hoffman/Barrett, L.L.C.
    Inventors: Brian M. Hoffman, Anthony G.M. Barrett
  • Patent number: 5910585
    Abstract: A process for the production of copper phthalocyanine, which overcomes the defect of a method using two reaction steps that since phthalimide formed in the first step adheres to the wall of a reactor and a stirring blade, the reaction in the second step does not smoothly proceed, so that the yield and the purity of the resultant pigment are low, and which process enables the industrially stable production of highly pure copper phthalocyanine at high yields,the process comprising the steps of(A) reacting phthalic anhydride or a phthalic anhydride derivative with ammonia to form phthalimide,(B) adding part or all of urea to the phthalimide obtained in step (A) and melting the mixture under heat to form a homogeneous slurry, and(C) adding copper or a copper compound and remaining urea if any to the slurry obtained in step (B) and forming a copper phthalocyanine or a copper phthalocyanine derivative in the presence of a catalyst.
    Type: Grant
    Filed: April 21, 1998
    Date of Patent: June 8, 1999
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Atsushi Endo, Yasumasa Suda
  • Patent number: 5889181
    Abstract: 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: Grant
    Filed: August 25, 1995
    Date of Patent: March 30, 1999
    Assignee: University Of Sherbrooke
    Inventors: Sveltana V. Kudrevich, Hasrat Ali, Johan E. Van Lier
  • Patent number: 5886160
    Abstract: 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: Grant
    Filed: June 12, 1998
    Date of Patent: March 23, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Zhimin Hao, John S. Zambounis, Abul Iqbal
  • Patent number: 5883245
    Abstract: 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: Grant
    Filed: October 2, 1997
    Date of Patent: March 16, 1999
    Assignee: Orient Chemical Industries, Ltd.
    Inventors: Yasuhiro Yamasaki, Tatsuto Yamashita
  • Patent number: 5880279
    Abstract: Cobalt dihalodihydroxydisulfophthalocyanines are useful in the extraction of low molecular weight mercaptans from petroleum (e.g., crude oil) or gas condensate.
    Type: Grant
    Filed: June 11, 1997
    Date of Patent: March 9, 1999
    Assignee: Chevron U.S.A. Inc.
    Inventors: Akhmet Mazgarovich Mazgarov, Azat Faridovich Vildanov, Nailya Gilmutdinovna Bazhirova, Gulnara Burkhanova Niamutdinova, Sergei Nikolaevich Sukhov
  • Patent number: 5874570
    Abstract: A titanyloxyphthalocyanine crystal to be used as a charge generation material for an electrophotographic photoreceptor, having a maximum diffraction intensity observed at Bragg angle (2 .theta.) of 9.6.degree..+-.0.2.degree. and clear peaks of diffraction intensity observed at 7.22.degree..+-.0.2.degree., 9.60.degree..+-.0.2.degree., 11.60.degree..+-.0.2.degree., 13.40.degree..+-.0.2.degree., 14.88.degree..+-.0.2.degree.,18.34.degree..+-.0.2.degree., 23.62.degree..+-.0.2.degree., 24.14.degree..+-.0.2.degree., and 27.32.degree..+-.0.2.degree., respectively, in an X-ray diffraction spectrum obtained by performing an x-ray diffraction method using CuK.alpha. as a source of radiation. A method for preparing the crystal includes dispersing a predetermined amount of amorphous titanyloxyphthalocyanine in an aqueous solution in which ionic substances are dissolved, under mechanical force at a temperature of under 50.degree. C.
    Type: Grant
    Filed: January 26, 1998
    Date of Patent: February 23, 1999
    Assignee: Fuji Electric Co., Ltd.
    Inventors: Shinichi Tamura, Youichi Tei, Naoki Itoh, Kazumi Egota, Kenichi Ohkura
  • Patent number: 5872248
    Abstract: 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: Grant
    Filed: March 28, 1997
    Date of Patent: February 16, 1999
    Assignee: Case Western Reserve University
    Inventors: Gongzhen Cheng, Guolun Hao, Hongqiao Wu, Ying-Syi Li, Malcolm E. Kenney
  • Patent number: 5859237
    Abstract: 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: Grant
    Filed: October 8, 1997
    Date of Patent: January 12, 1999
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Hideko Noguchi, Mikio Hayashi, Masatoshi Momose
  • Patent number: 5847114
    Abstract: 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: Grant
    Filed: October 25, 1995
    Date of Patent: December 8, 1998
    Assignee: Zeneca Limited
    Inventors: Dean Thetford, Peter Gregory
  • Patent number: 5847111
    Abstract: Novel aluminium phthalocyanine compounds of having the formula ##STR1## and their salts wherein D represents --SO.sub.2 NR.sub.a --A--SO.sub.2 --B or ##STR2## --SO.sub.2 B is a fiber-reactive group and Z is a heterocyclic fiber-reactive group having 1 or 2 labile halogens selected from fluorine or chlorine.The novel aluminium phthalocyanine compounds and their salts are fiber-reactive dyestuffs useful in dyeing or printing hydroxy-group-containing or nitrogen-containing organic substrates.
    Type: Grant
    Filed: December 11, 1996
    Date of Patent: December 8, 1998
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Roland Wald, Markus Gisler
  • Patent number: 5834608
    Abstract: 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: Grant
    Filed: May 30, 1996
    Date of Patent: November 10, 1998
    Assignee: Kawasaki Kasei Chemicals Ltd.
    Inventor: Kazuhiro Maruyama
  • Patent number: 5830267
    Abstract: The invention relates to the coloration of high molecular weight organic materials in the mass with soluble phthalocyanine precursors of structure ##STR1## or isomers thereof, to the soluble phthalocyanine precursors as such wherein M is Zn, Ti or V or wherein L.sub.1 is morpholino, pyrrolidino or with C.sub.1 -C.sub.12 alkyl substituted piperidino, to compositions containing high molecular weight organic materials and the above soluble phthalocyanine precursors, and to a process for making structured color images and applications thereof.
    Type: Grant
    Filed: May 6, 1996
    Date of Patent: November 3, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: John Zambounis, Heinz Wolleb
  • Patent number: 5824800
    Abstract: 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: Grant
    Filed: June 21, 1996
    Date of Patent: October 20, 1998
    Assignee: Fuji Electric Co., Ltd.
    Inventors: Shinichi Tamura, Seishi Terasaki, Tadashi Mimura, Teruaki Kobayashi, Youichi Tei
  • Patent number: 5824799
    Abstract: 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: Grant
    Filed: March 22, 1996
    Date of Patent: October 20, 1998
    Assignee: Biosite Diagnostics Incorporated
    Inventors: Kenneth F. Buechler, Joseph B. Noar, Lema Tadesse
  • Patent number: 5817805
    Abstract: 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: Grant
    Filed: February 21, 1997
    Date of Patent: October 6, 1998
    Assignee: Eastman Kodak Company
    Inventors: William T. Gruenbaum, Chang K. Kim, Cataldo A. Magguilli, Robert J. Opitz
  • Patent number: 5817154
    Abstract: 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: Grant
    Filed: August 29, 1995
    Date of Patent: October 6, 1998
    Assignee: Zeneca Limited
    Inventors: Peter Gregory, Stephen James Reynolds, Raymond Lesley White
  • Patent number: 5817804
    Abstract: 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: Grant
    Filed: April 23, 1997
    Date of Patent: October 6, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventor: Heinz Wolleb
  • Patent number: 5811543
    Abstract: 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: Grant
    Filed: July 9, 1996
    Date of Patent: September 22, 1998
    Assignee: Ciba Speciality Chemicals Corporation
    Inventors: Zhimin Hao, John S. Zambounis, Abul Iqbal
  • Patent number: 5792860
    Abstract: 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: Grant
    Filed: September 25, 1996
    Date of Patent: August 11, 1998
    Assignee: 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 Agency
    Inventors: Neil Bruce McKeown, Kevin Edward Treacher, Guy James Clarkson
  • Patent number: 5789582
    Abstract: A nuclear halogenated aromatic compound possessing cyano groups is produced by a method using as a raw material an aromatic compound which possesses cyano groups and assumes a solid state at room temperature and subjecting the raw material to a procedure comprising a step of melting and transporting the compound by a means transport-melting, a step of vaporizing the compound, a step of mixing the compound with a halogen gas, and a step of causing the vapor of the compound to react with the halogen gas in vapor phase in the presence of a catalyst sequentially in the order mentioned, which comprises maintaining a content of a self-condensate of the aromatic compound possessing cyano groups which arise during the melting of the aromatic compound possessing cyano groups in a gas of the compound which reacts with the halogen gas to a level of not more than 2.5 mol % based on the compound.
    Type: Grant
    Filed: March 7, 1997
    Date of Patent: August 4, 1998
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Osamu Kaieda, Koichi Hirota, Teruhisa Kajiwara, Norimasa Okuda, Hisakazu Shindo, Yoshiro Hanayama, Yujin Shoda, Toyohiko Kohno, deceased, Takashi Yodoshi, Masaru Awashima
  • Patent number: 5783694
    Abstract: Compounds of the general formula I ##STR1## where the A radicals are, independently of one another, ##STR2## where the rings B and C can also, independently of one another, be substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, nitro, hydroxysulfonyl, benzoyl or a fused-on benzo ring,R is hydrogen or methyl, and the two hydrogen atoms on the nitrogens Can be replaced by copper, nickel, vanadyl, magnesium, AlCl or zinc,are suitable as IR-absorbers.
    Type: Grant
    Filed: March 24, 1997
    Date of Patent: July 21, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Hagen, Bernhard Albert
  • Patent number: 5780621
    Abstract: Phthalocyanines of the formula ##STR1## in which Z is a fiber-reactive radical and the other substituents and indices have the meaning given in the description, have improved use properties.
    Type: Grant
    Filed: August 8, 1996
    Date of Patent: July 14, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Harms, Karl-Josef Herd, Willi Brust
  • Patent number: 5776576
    Abstract: 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: Grant
    Filed: October 7, 1996
    Date of Patent: July 7, 1998
    Assignees: Hirofusa Shirai, TDK Corporation
    Inventors: Mutsumi Kimura, Hirofusa Shirai, Toshiki Koyama, Kenji Hanabusa, Yuichi Kubota
  • Patent number: 5773609
    Abstract: A broad class of photosensitive compounds having enhanced in vivo target tissue selectivity and versatility in photodynamic therapy. Many furocoumarin compounds, such as psoralens, exhibit cytostatic activity when photoactivated but exhibit little in vivo specificity for selectively accumulating in any particular target tissue such as atheromatous plaques. Reactive Oxygen Producing Photosensitizers ("ROPPs") are photoactivatable compounds having an affinity for hyperproliferating cells (such as atheromatous plaque cells), which when photoactivated, produce cytotoxic reaction products. The photoactivity of a ROPP, such as a porphyrin, may be reduced by metalating the porphyrin while the selective affinity of the metalized ROPP for hyperproliferating tissue remains substantially unchanged.
    Type: Grant
    Filed: February 14, 1997
    Date of Patent: June 30, 1998
    Assignee: PDT Pharmaceuticals, Inc.
    Inventors: Byron Robinson, Alan R. Morgan, Hugh L. Narciso, Jr.
  • Patent number: 5766268
    Abstract: A colorant composition which can be liquid in the neat form at 25.degree. C., having the structure ABXYZ, whereA is an organic chromophore;B is an electrophilic reactive group covalently bonded to A directly or through a linking group;X is a nucleophilic linking group covalently bonding B and Y;Y is a poly(oxyalkylene)-containing moiety comprising the formula (C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n where a and b are different and from 1 to 8, m is at least 3, n is 0 to 15; andZ is a terminal group for Y.The colorant composition can be prepared from a reactive dye AB which is reacted with XYZ, a poly(oxyalkylene)-containing moiety containing a nucleophilic group.
    Type: Grant
    Filed: March 13, 1997
    Date of Patent: June 16, 1998
    Assignee: Milliken Research Corporation
    Inventor: John D. Bruhnke
  • Patent number: 5763601
    Abstract: 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: Grant
    Filed: February 25, 1997
    Date of Patent: June 9, 1998
    Assignees: Hirofusa Shirai, TDK Corporation
    Inventors: Hirofusa Shirai, Mutsumi Kimura, Yuichi Kubota
  • Patent number: 5759254
    Abstract: 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: Grant
    Filed: July 18, 1996
    Date of Patent: June 2, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Ian Alexander Macpherson, Iain Frank Fraser, Sharon Kathleen Wilson
  • Patent number: 5750229
    Abstract: 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.4 is substituted by the halogen atom; X is a halogen atom; each of k, l, m and n is independently a value of from 0 to 3; each of o, p, q and r is independently a value of 0, 1 or 2, and all of them are not 0 simultaneously; each sum of k and o, l and p, m and q, and n and r is independently in the range of from 0 to 4; Met is two hydrogen atoms, a di, monosubstituted tri, disubstituted ter metal atom or an oxymetal atom. The above phthalocyanins can be used to provide optical recording medium.
    Type: Grant
    Filed: January 6, 1997
    Date of Patent: May 12, 1998
    Assignees: Mitsui Toatsu Chemicals, Inc., Yamamoto Chemicals, Inc.
    Inventors: Takahisa Oguchi, Hideki Umehara, Kenichi Sugimoto, Ryu Oi, Hisato Itoh
  • Patent number: 5739318
    Abstract: 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: Grant
    Filed: July 12, 1993
    Date of Patent: April 14, 1998
    Assignee: Axis Research AS
    Inventors: Frank Frantzen, Erling Sundrehagen
  • Patent number: 5739319
    Abstract: 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: Grant
    Filed: September 13, 1996
    Date of Patent: April 14, 1998
    Assignee: Orient Chemical Industries, Ltd.
    Inventor: Yasuhiro Yamasaki
  • Patent number: 5686439
    Abstract: 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: Grant
    Filed: December 15, 1995
    Date of Patent: November 11, 1997
    Assignee: Novartis Corporation
    Inventors: Hans Georg Capraro, Marcus Baumann
  • Patent number: 5677199
    Abstract: 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: Grant
    Filed: November 29, 1994
    Date of Patent: October 14, 1997
    Assignee: Diatron Corporation
    Inventor: Peter Olof Gustaf Arrhenuis
  • Patent number: 5675001
    Abstract: 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: Grant
    Filed: March 14, 1995
    Date of Patent: October 7, 1997
    Assignee: Hoffman/Barrett, L.L.C.
    Inventors: Brian M. Hoffman, Anthony G. M. Barrett
  • Patent number: 5675002
    Abstract: Purification of hydrophobic solids by forming granules in the presence of water comprises treating the solids, if desired more than once, with one or more different two-phase systems comprisingA) a phase which wets the solids and effects granule formation and which consists essentially of one or more water-immiscible or partially water-miscible organic liquids, andB) a phase which takes up the impurities and which consists essentially ofB1) water, one or more water-miscible organic liquids and if desired an inorganic acid or an inorganic base, orB2) water and an inorganic acidin the heat and subsequently separating the resulting granules from the aqueous phase.
    Type: Grant
    Filed: January 20, 1995
    Date of Patent: October 7, 1997
    Assignee: BASF Aktiengesellschaft
    Inventor: Karl Schmeidl
  • Patent number: 5670491
    Abstract: 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: Grant
    Filed: June 30, 1994
    Date of Patent: September 23, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans Georg Capraro, Marcus Baumann