Phthalocyanines Patents (Class 540/122)
  • 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
  • Patent number: 5663326
    Abstract: 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: September 18, 1995
    Date of Patent: September 2, 1997
    Assignee: Ciba-Geigy Corporation
    Inventor: Heinz Wolleb
  • Patent number: 5656752
    Abstract: 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: Grant
    Filed: September 28, 1995
    Date of Patent: August 12, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Kipper, Bernhard Albert
  • Patent number: 5646273
    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.
    Type: Grant
    Filed: September 20, 1995
    Date of Patent: July 8, 1997
    Assignees: Mitsui Toatsu Chemicals, Inc., Yamamoto Chemicals, Inc.
    Inventors: Takahisa Oguchi, Hideki Umehara, Kenichi Sugimoto, Ryu Oi, Hisato Itoh
  • Patent number: 5641879
    Abstract: The invention relates to phthalocyanines and metal complexes thereof with divalent metals or divalent oxo metals, which contain at least one phosphorus-containing substituent bonded to the peripheral carbon skeleton via the phosphorus atom.The compounds preferably conform to the general structural formula (G).sub.k -A-(Q).sub.l, in which A is a phthalocyanine or metal complex thereof with a divalent metal or a divalent oxo metal, G is a phosphorus-containing substituent, Q is a further substituent as defined below, the index k is a number from 1 to 16, and l, independently thereof, is 0 or a number from 1 to 15, with the proviso that the sum of k and l is a number less than or equal to 16.The invention also relates to a material for the optical recording and storage of information, in which at least one storage layer (2) of a novel phthalocyanine compound or a metal complex thereof has been applied to a transparent, dielectric carrier material (1).
    Type: Grant
    Filed: September 20, 1995
    Date of Patent: June 24, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Heinz Wolleb, Hanspeter Preiswerk, Beat Schmidhalter, Heinz Spahni
  • Patent number: 5633370
    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: October 21, 1994
    Date of Patent: May 27, 1997
    Assignees: Hirofusa Shirai, TDK Corporation
    Inventors: Hirofusa Shirai, Mutsumi Kimura, Yuichi Kubota
  • Patent number: 5629418
    Abstract: 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: Grant
    Filed: October 27, 1994
    Date of Patent: May 13, 1997
    Assignee: Eastman Kodak Company
    Inventors: Michel F. Molaire, Jeanne E. Kaeding, William T. Gruenbaum
  • Patent number: 5629417
    Abstract: 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: Grant
    Filed: January 31, 1996
    Date of Patent: May 13, 1997
    Assignee: Zeneca Limited
    Inventors: James S. Campbell, Peter Gregory, Dean Thetford
  • Patent number: 5622685
    Abstract: Tumor-active or tumor-diagnostic substances having preferred accumulation in the tumor, which are characterized in that they haveat least two phenolic hydroxyl and/or amino groups,at least one aliphatic amino group, orat least one phenolic hydroxyl and/or amino group andat least one aliphatic amino groupand that these groups are substituted with polyethylene glycol chains whose polymerization degree n is 5 to 250 and whose terminal hydroxyl group is substituted by C.sub.1 -C.sub.12 alkyl ester or ether, each of the substances being substituted by at least two such polyethylene glycol chains.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: April 22, 1997
    Assignee: Deutches Krebsforchunszentrum Stiftung des Offentlichen Rechts
    Inventors: Hans J. Sinn, Hans-Hermann Schrenk, Wolfgang Maier-Borst, Eckhard Friedrich, Georgi Graschew, Dieter Wohrle, Thomas Klenner
  • Patent number: 5618930
    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: March 1, 1996
    Date of Patent: April 8, 1997
    Assignees: Hirofusa Shirai, TDK Corporation
    Inventors: Mutsumi Kimura, Hirofusa Shirai, Toshiki Koyama, Kenji Hanabusa, Yuichi Kubota
  • Patent number: 5618929
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: April 8, 1997
    Assignee: The Secretary of State for Defence in Her Brittanic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Kenneth J. Harrison, Michael J. Cook, Andrew J. Thomson, Neil B. McKeown, Mervyn F. Daniel, Adrian J. Dunn
  • Patent number: 5602249
    Abstract: 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: Grant
    Filed: March 29, 1995
    Date of Patent: February 11, 1997
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventor: Michichika Hikosaka
  • Patent number: 5594128
    Abstract: A process for the preparation of a mixture of positionally isomeric brominated tetraalkoxymetal phthalocyanines of the formula I, ##STR1## where Me is Cu(II), Pd(II), Zn(II), Sn(II), Ni(II), Co(II), Pb(II), Mn(O) or V(O), x is a number from 1 to 5, and R.sub.1 to R.sub.4, independently of one another, are 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 radicals which are 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,by reacting a tetraalkoxy metal phthalocyanine of the formula II with bromine, ##STR2## which comprises carrying out the reaction in a halogenated, aromatic solvent, essentially water-immiscible in the presence of a second, aqueous phase.
    Type: Grant
    Filed: September 20, 1995
    Date of Patent: January 14, 1997
    Assignee: Ciba-Geigy Corporation
    Inventor: Heinz Wolleb
  • Patent number: 5591555
    Abstract: An electrophotographic photoconductor, includes metal-free phthalocyanine as a charge-generating substance, wherein the X-ray diffraction spectrum of said metal-free phthalocyanine as measured using CuK.alpha. as a radiation source includes intense diffraction peaks at Bragg angles (2.theta..+-.0.2.degree.) of 7.5.degree., 9.0.degree., 16.6.degree., 17.2.degree., 21.5.degree., 22.2.degree., 23.8.degree., and 28.5.degree., and wherein the infrared absorption spectrum of said metal-free phthalocyanine includes four absorption bands with the maximum absorption intensity at a wavenumber of 716 cm.sup.-1 between a wavenumber of 700 cm.sup.-1 and a wavenumber of 760 cm.sup.-1 and a characteristic absorption band at a wavenumber of 3,291.+-.2 cm.sup.-1.
    Type: Grant
    Filed: January 10, 1995
    Date of Patent: January 7, 1997
    Assignee: Fuji Electric Co., Ltd.
    Inventors: Shinichi Tamura, Seishi Terasaki, Tadashi Mimura, Teruaki Kobayashi, Youichi Tei
  • Patent number: 5585483
    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: October 20, 1995
    Date of Patent: December 17, 1996
    Assignee: Fuji Electric., Ltd.
    Inventors: Shinichi Tamura, Seishi Terasaki, Tadashi Mimura, Teruaki Kobayashi, Youichi Tei
  • Patent number: 5582774
    Abstract: 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: Grant
    Filed: February 26, 1991
    Date of Patent: December 10, 1996
    Assignees: Mitsui Toatsu Chemicals, Incorporated, Yamamoto Chemicals, Incorporated
    Inventors: Hisato Itoh, Katashi Enomoto, Takahisa Oguchi, Tsutomu Nishizawa
  • Patent number: 5569758
    Abstract: A process for preparing metal-free phthalocyanines which can carry up to 16 halogen atoms, cyano groups, carboxyl groups, sulfo groups, C.sub.1 -C.sub.18 -alkyl groups and/or aryl radicals as substituents by reductive cyclization of ortho-phthalodinitrile substituted ortho-phthalodinitriles or mixtures thereof comprises effecting the cyclization in C.sub.2 -C.sub.4 -alkylene monoglycols, oligoglycols or polyglycols, their mono-C.sub.1 -C.sub.4 -alkyl or -aryl ethers or their mixtures in the presence of an aromatic compound of the formula I ##STR1## where the substituents X can be identical or different and each denotes hydroxyl, mercapto, amino or C.sub.1 -C.sub.6 -alkylamino, the substituents Y can likewise be identical or different and each denotes halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -alkoxycarbonyl, m is from 1 to 4 and n is from 0 to 5, subject to the proviso that m+n .ltoreq.
    Type: Grant
    Filed: December 16, 1994
    Date of Patent: October 29, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Ingo Klopp, Peter B ottcher, Ulrich Frick, Otto Schiller
  • Patent number: 5563260
    Abstract: The compounds of general formula I ##STR1## wherein R represents chlorine or hydroxylPc represents a phthalocyanine radicalR.sub.1 may be alkyl and R.sub.2 may be alkyl ammoniumare excellently suitable for dyeing of plastic materials, paper and inks for ball point pens.
    Type: Grant
    Filed: February 9, 1995
    Date of Patent: October 8, 1996
    Assignee: Sandoz Ltd.
    Inventors: Bansi L. Kaul, Dominique Pflieger
  • Patent number: 5556966
    Abstract: 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: Grant
    Filed: July 19, 1994
    Date of Patent: September 17, 1996
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Shuuichi Kimura, Michichika Hikosaka, Masami Shirao, Akimitsu Mochizuki, Junichi Tsuchida
  • Patent number: 5534055
    Abstract: This invention relates to a process for preparing alpha-phase metal phthalocyanine pigments from crude metal phthalocyanine pigments comprising(a) acid pasting or acid swelling a crude metal phthalocyanine pigment;(b) dry milling the acid-pasted or acid-swelled metal phthalocyanine pigment in the presence of 5 to 50 parts by weight of a stabilizer per 100 parts by weight of the crude metal phthalocyanine pigment until the average particle size is reduced to less than about 0.5 .mu.m;(c) finishing the milled metal phthalocyanine pigment by thoroughly mixing said milled metal phthalocyanine pigment with a finishing solvent mixture comprising 3 to 6 parts by weight, relative to the crude metal phthalocyanine pigment, of water and 0.4 to 1.
    Type: Grant
    Filed: August 24, 1994
    Date of Patent: July 9, 1996
    Assignee: Bayer Corporation
    Inventors: Herman Gerson, Abdul Sattar
  • Patent number: 5516899
    Abstract: 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: Grant
    Filed: July 20, 1994
    Date of Patent: May 14, 1996
    Assignee: Zeneca Limited
    Inventors: James S. Campbell, Peter Gregory, Dean Thetford
  • Patent number: 5516901
    Abstract: Reactive phthalocyanine dyes are prepared by reacting phthalocyaninesulfonyl chlorides with amines containing a reactive group and subjecting the resulting reaction mixture to a membrane treatment.
    Type: Grant
    Filed: December 10, 1993
    Date of Patent: May 14, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Dornhagen, Manfred Patsch
  • Patent number: 5506708
    Abstract: 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: Grant
    Filed: July 17, 1989
    Date of Patent: April 9, 1996
    Assignee: The Secretary of State for Defence in Her Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Kenneth J. Harrison, Michael J. Cook, Andrew J. Thomson, Neil B. McKeown, Mervyn F. Daniel, Adrian J. Dunn
  • Patent number: 5492563
    Abstract: Copper phthalocyanine pigments are finely divided in an ecologically and economically advantageous manner by first of all subjecting crude, coarsely crystalline copper phthalocyanine pigments to dry milling and then wet milling the finely divided prepigments which are obtained in the course of dry milling, in aqueous suspension and with the addition of from 0.1 to 5% by weight, based on the total millbase, of an organic solvent which is inert with respect to the process conditions, on a stirred ball mill which is operated at an energy density of more than 2.5 kW per liter of milling space and a peripheral stirrer speed of more than 12 m/s under the action of grinding media having a diameter of less than or equal to 1 mm. Copper phthalocyanine pigments prepared in this way are particularly suitable as colorants for pigmenting paints, printing inks and plastics.
    Type: Grant
    Filed: April 13, 1995
    Date of Patent: February 20, 1996
    Assignee: Hoechst AG
    Inventor: Manfred Urban
  • Patent number: 5491228
    Abstract: A process for the preparation of dihydroxygermanium phthalocyanine, polymorphic Type III, which comprises treating dihalogermanium phthalocyanine or dialkoxygermanium phthalocyanine with a strong acid, followed by treatment with water, optionally washing with a dilute aqueous base and water, and subsequently optionally admixing with a solvent mixture comprised of a strong organic acid and aprotic organic solvent.
    Type: Grant
    Filed: April 18, 1994
    Date of Patent: February 13, 1996
    Assignee: Xerox Corporation
    Inventors: Beng S. Ong, Cheng-Kuo Hsiao
  • Patent number: 5484915
    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. Compositions comprising one or more compounds of Formula (1) and their use as cleaning materials are also disclosed along with a process for removing stains and/or grime from fabrics using these compositions.
    Type: Grant
    Filed: July 6, 1994
    Date of Patent: January 16, 1996
    Assignee: Zeneca Limited
    Inventors: Peter Gregory, Stephen J. Reynolds, Raymond L. White
  • Patent number: 5466796
    Abstract: Alkoxy-bridged metallophthalocyanine dimers of the formula C.sub.32 H.sub.16 N.sub.8 MOROMN.sub.8 H.sub.16 C.sub.32, or of the formula ##STR1## wherein M is a metal, and R is an alkyl or an alkyl ether.
    Type: Grant
    Filed: April 26, 1994
    Date of Patent: November 14, 1995
    Assignee: Xerox Corporation
    Inventors: Richard A. Burt, George Liebermann, Gordon K. Hamer, Sandra J. Gardner, Carol A. Jennings, Katsumi Daimon, Katsumi Nukada
  • Patent number: 5463044
    Abstract: A process for preparing chlorogallium phthalocyanine comprising the steps of: reacting gallium trichloride and phthalonitrile or diiminoisoindoline in an aromatic hydrocarbon solvent; and treating the resulting chlorogallium phthalocyanine with a second solvent different from the aromatic hydrocarbon solvent.
    Type: Grant
    Filed: August 18, 1993
    Date of Patent: October 31, 1995
    Assignee: Fuji Xerox Co., Ltd.
    Inventors: Katsumi Nukada, Akira Imai, Masakazu Iijima
  • Patent number: 5446142
    Abstract: The present invention provides a light-absorbing compound represented by the formula (I):Dye-(OR.sup.1)(OR.sup.2)(OR.sup.3) . . . (OR.sup.n) (I)wherein Dye is a light-absorbing compound residue having at least one aromatic ring; OR.sup.1 to OR.sup.n are substituents on the aromatic ring, and are independently (a) substituted or unsubstituted saturated hydrocarbonoxy groups having 1 to 20 carbon atoms, or (b) substituted or unsubstituted unsaturated hydrocarbonoxy groups having 2 to 20 carbon atoms, and at least one of OR.sup.1 to OR.sup.n is an unsaturated hydrocarbonoxy group; and n is a value of from 1 to 10. The present invention also provides an optical recording medium containing the above-mentioned light-absorbing compound in a recording layer.
    Type: Grant
    Filed: June 11, 1993
    Date of Patent: August 29, 1995
    Assignees: Mitsui Toatsu Chemicals, Inc., Yamamoto Chemicals, Inc.
    Inventors: Hisato Itoh, Takahisa Oguchi, Kenichi Sugimoto, Ryu Oi, Hideki Umehara, Shin Aihara
  • Patent number: 5437929
    Abstract: A process for preparing film structures comprising phthalocyanine oligomers having metal coordinating atoms in adjacent rings connected along a central axis through oxygen atoms. The ligands on the outermost rings of the structures are hydrophilic. The preferred coordinating atom is germanium and the structures may be prepared on a Langmuir-Blodgett balance using phthalocyanine oligomers in which one of the outermost rings is connected to a hydrophobic ligand while the other outermost ring is connected to a hydrophilic ligand. The pH of the subphase in the trough of the balance is maintained at a pH of from about 2 to 6, and the hydrophobic ligand is converted to a hydrophilic ligand during the process of coating a substrate by passing it upward through the film on the subphase.
    Type: Grant
    Filed: January 19, 1994
    Date of Patent: August 1, 1995
    Assignee: Edison Polymer Innovation Corp.
    Inventors: Malcom E. Kenney, Terri R. Clark
  • Patent number: 5432277
    Abstract: Metal-free phthalocyanine of the .gamma.-form is suitable inter alia for coloring printing inks, plastics and coatings and is characterized by the X-ray powder diagram (Cu.sub.K.alpha.) having the essential glancing angles 2 theta [.degree.]6.8, 7.4, 13.6, 14.9, 15.9, 16.9, 20.5, 22.4, 24.7, 26.2 and 27.8, possibly in mixture with other crystal forms, in which case the glancing angles may be shifted by .+-.0.2.degree. (FIG. 1).
    Type: Grant
    Filed: October 15, 1993
    Date of Patent: July 11, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Boettcher, Peter Erk, Joachim Jesse
  • Patent number: 5427616
    Abstract: A process for the production of a copper phthalocyanine pigment composition from 70 to 99% by weight of a crude copper phthalocyanine and 30 to 1% by weight of a phthalocyanine derivative,the crude copper phthalocyanine being converted to a pigment without a large amount of energy and the treatment of exhaust water,the copper phthalocyanine pigment composition having excellent fluidity, tinting strength and stability with time when used in a coating composition or a printing ink,the copper phthalocyanine pigment composition showing almost no "strike-through" when used for gravure printing on low-quality paper,the process comprising dry milling the entirety of the crude copper phthalocyanine and the phthalocyanine derivative in an amount of 0.5 to 10% by weight of a final composition in the absence of a milling auxiliary until the content of an .alpha.
    Type: Grant
    Filed: June 1, 1994
    Date of Patent: June 27, 1995
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Kosaku Tsuji, Yoshio Muramatsu, Shigeki Kato
  • Patent number: 5367069
    Abstract: Metal-free phthalocyanines in the .chi.-modification substituted in up to four ortho positions can be prepared by tetramerisation of a reaction mixture consisting of phthalonitriles substituted in the 3-position with phthalonitrile in a molar ratio of 4:0 to 1:40 in the presence of a base and subsequent heat treatment at temperatures of between 100.degree. and 300.degree. C. They constitute excellent organic pigments.
    Type: Grant
    Filed: May 10, 1993
    Date of Patent: November 22, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunther Beck, Bernd Kaletta
  • Patent number: 5318623
    Abstract: A process for producing a metal phthalocyanine pigment which comprises the steps of: reacting phthalic anhydride or a derivative thereof with urea or a derivative thereof with heating in the presence of a catalyst either in the presence or absence of an organic solvent; adding to the reaction mixture of the preceding step a metal or its compound capable of constituting the core of the metal phthalocyanine either alone or together with urea or a derivative thereof, without isolating the reaction product from the reaction mixture of the preceding step; and allowing the reaction mixture to react while simultaneously applying a mechanical grinding force in the presence or absence of a grinding agent.
    Type: Grant
    Filed: April 30, 1993
    Date of Patent: June 7, 1994
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Shinichi Azuma, Takashi Kano, Takanori Miyake, Hideo Shimizu
  • Patent number: 5296034
    Abstract: Copper phthalocyanine pigments and pigment preparations in the .alpha. phase are prepared with phase conversion from copper phthalocyanine crude pigments of the .beta. phase in an environmentally safe and economical manner bya) first wet milling a copper phthalocyanine pigment, which is predominantly present in the .beta. phase, in an aqueous, preferably neutral to alkaline medium in a stirred ball mill which is operated at a power density of more than 2.
    Type: Grant
    Filed: June 18, 1993
    Date of Patent: March 22, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Erwin Dietz, Manfred Urban
  • Patent number: 5296033
    Abstract: Phthalocyanine pigments and phthalocyanine pigment preparations in the .alpha. phase and in the .beta. phase are prepared with phase conservation in an environmentally safe and economical manner bya) first wet milling a phthalocyanine pigment in an inert liquid medium in a stirred ball mill which is operated at a power density of more than 2.
    Type: Grant
    Filed: June 18, 1993
    Date of Patent: March 22, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Erwin Dietz, Manfred Urban
  • Patent number: 5284511
    Abstract: The present invention relates to a process for preparing a beta-phase metal phthalocyanine pigments in which(a) a crude metal phthalocyanine having an average particle size of about 10 to about 200 .mu.M is dry milled until the average particle size is reduced to about 0.01 to about 0.5 .mu.m;(b) the milled metal phthalocyanine is finished by thoroughly mixing said metal phthalocyanine with at least about 4 parts by weight, relative to the metal phthalocyanine, of a finishing solvent containing a mixture of(i) about 5 to 100 percent by weight, based on the total amount of finishing solvent, of a monocarboxylic acid monoester, dicarboxylic acid diester, diol diester, lactone, or cyclic carbonate, or a mixture thereof, and(ii) 0 to about 95 percent by weight, based on the total amount of finishing solvent, of water;(c) the ester used in step (b) is hydrolyzed; and(d) the beta-phase metal phthalocyanine pigment is collected.
    Type: Grant
    Filed: April 12, 1993
    Date of Patent: February 8, 1994
    Assignees: Miles Inc., Bayer Aktiengesellschaft
    Inventors: Meinhard Rolf, Abdul Sattar
  • Patent number: 5281616
    Abstract: Compositions for the inhibition of replication of human immunodeficiency virus containing one or more "porphyrins" possessing antiviral activity. As used herein "porphyrins" includes porphyrins, phthalocyanines, chlorins, metallo derivatives thereof, and other porphyrin-like compounds. Examples of natural and synthetic, positively, negatively, and neutrally charged porphyrins, phthalocyanines, and derivatives thereof have been found to exhibit selective anti-HIV activity which is not dependent on the presence of light.
    Type: Grant
    Filed: April 24, 1992
    Date of Patent: January 25, 1994
    Assignees: Georgia State University Foundation, Inc., Emory University
    Inventors: Dabney W. Dixon, Raymond F. Schinazi, Luigi G. Marzilli
  • Patent number: 5281268
    Abstract: A process for the production of a .beta.-form copper phthalocyanine having a particle size of 0.005 to 0.2 .mu.m and an aspect ratio of 1 to 3, which comprises the following steps:a. dry-milling a crude copper phthalocyanine in a milling apparatus until the resultant dry-milled product has an .alpha.-crystal content of more than 45% by weight,wet-milling the resultant dry-milled product in the presence of a water-soluble inorganic salt and at least one organic liquid selected from the group consisting of water-soluble alkylene glycols having 2 to 3 carbon atoms and polyoxyalkylene glycols, wherein the inorganic salt is used in an amount that is 2 to 10 times, by weight, as large as that of the dry-milled copper phthalocyanine, and wherein the organic liquid is used in an amount that is 0.1 to 2 times, by weight, as large as that of the dry-milled copper phthalocyanine, andc. removing the inorganic salt and the organic liquid from the resultant wet-milled product.
    Type: Grant
    Filed: April 23, 1993
    Date of Patent: January 25, 1994
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Yusaku Ide, Toshimitsu Ikegaya, Michichika Hikosaka
  • Patent number: 5280114
    Abstract: Halogenated alkoxyphthalocyanine having a controlled grade of halogenation can be prepared by reacting a single compound or a mixture of phthalocyanine represented by the formula (1): ##STR1## wherein R.sup.1 is a substituted or unsubstituted alkyl group and may be the same or different, and Met is two hydrogen atoms, a divalent metal atom or a trivalent or tetravalent metal derivative, with 1 to 6 mole ratio of a halogenating agent at 0.degree. to 260.degree. C. in a solvent of from 1 to 1000 times by weight.
    Type: Grant
    Filed: July 12, 1991
    Date of Patent: January 18, 1994
    Assignees: Mitsui Toatsu Chemicals, Incorporated, Yamamoto Chemicals, Incorporated
    Inventors: Hisato Itoh, Takahisa Oguchi, Shin Aihara
  • Patent number: 5264032
    Abstract: Pigment preparation essentially comprisinga) at least one pigment from the class of azo, anthrapyrimidine, anthanthrone, quinacridone, perinone, diketopyrrolopyrrole, dioxazine, flavanthrone, indanthrone, isoindolinone, isoviolanthrone, perylene, phthalocyanine, pyranthrone or thioindigo pigments or a mixture of pigments belonging to various classes, andb) at least one dispersant of the formula (I) ##STR1## in which P, independently of the pigments mentioned in a), is a radical of an anthanthrone azo, quinacridone, perinone, diketopyrrolopyrrole, dioxazine, indanthrone, perylene, phthalocyanine or thioindigo pigment,R.sup.1 and R.sup.2, independently of one another, are hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.
    Type: Grant
    Filed: October 21, 1992
    Date of Patent: November 23, 1993
    Assignee: Hoechst AG
    Inventors: Erwin Dietz, Manfred Urban
  • Patent number: 5260435
    Abstract: A derivative of naphthalocyanine containing a perfluoroalkyl group and having a particular structure for ensuring excellent weather-proof properties, extremely high solubility in various solvents and capability of forming a film, and an optical recording medium prepared by using the derivative and capable of recording while using a focused beam of a semiconductor laser or the like. The derivative of naphthalocyanine containing a perfluoroalkyl group may be prepared by reacting a perfluoroalkanoyl peroxide having a particular structure with a naphthalocyanine.
    Type: Grant
    Filed: March 18, 1992
    Date of Patent: November 9, 1993
    Assignees: Nippon Oil and Fats Co., Ltd., Hitachi Chemical Co., Ltd.
    Inventors: Hideo Sawada, Motohiro Mitani, Masaharu Nakayama, Yoshii Morishita, Mitsuo Katayose, Tadashi Okamoto, Nobuyuki Hayashi
  • Patent number: 5204203
    Abstract: A photosensitive material for electrophotography, comprises a support and, provided thereon, an organic photoconductive layer of single-layer structure comprising a mixture of a metal-free phthalocyanine and a binder organic compound; said binder organic compound being comprised of an isocyanate in which the isocyanate terminal has been blocked with a blocking agent.The present photosensitive material can achieve good sensitivity and charge characteristics and is suited for the positive charge system.
    Type: Grant
    Filed: November 20, 1991
    Date of Patent: April 20, 1993
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Yoshimasa Ito, Sohji Tsuchiya, Mutsuaki Murakami, Atsushi Omote
  • Patent number: 5189153
    Abstract: A phthalocyanine compound of the Formula (1): ##STR1## wherein: Pc is a phthalocyanine nucleus which is metal free or contains a metal or oxymetal;X is S; NT or O;Y is S; NT or O;Z is S or Se; in which T in the above is H; alkyl or aryl;.sup.+ HA is an aliphatic polyamino ammonium ion or a substituted diguanidinium ion;each R independently is an aromatic radical linked to a peripheral carbon atom of the Pc nucleus through an atom Z;each R.sup.1 independently is optionally substituted phenylene or naphthylene in which the atoms X and Y are attached to adjacent nuclear carbon atoms in R.sup.1 and to adjacent peripheral carbon atoms of the Pc nucleus;a is 0 to 16; provided thatb is 0 to 8; a+b>0; andc+d is 1 to 16.
    Type: Grant
    Filed: June 19, 1990
    Date of Patent: February 23, 1993
    Assignee: Imperial Chemical Industries, PLC
    Inventors: Peter Gregory, Prakash Patel
  • Patent number: 5177200
    Abstract: A colorant for natural or synthetic resinous or polymeric materials, having the formula A--[SO.sub.2 --N(R.sub.2)--Y].sub.1-4 ; wherein: R.sub.
    Type: Grant
    Filed: May 19, 1989
    Date of Patent: January 5, 1993
    Assignee: Milliken Research Corporation
    Inventors: Edward W. Kluger, John W. Rekers, David J. Moody
  • Patent number: 5168022
    Abstract: In a process for preparing a photoconductive pigment having a small particle size, a polymorph of a pigment is produced by a conversion process wherein a seed amount of the desired polymorph of the pigment and a larger amount of another polymorph of the pigment are subjected to a liquid jet interaction process.
    Type: Grant
    Filed: December 31, 1990
    Date of Patent: December 1, 1992
    Assignee: Xerox Corporation
    Inventors: Eric B. Wasmund, T. Edward Petroff
  • Patent number: 5087390
    Abstract: In one embodiment this invention provides a tetraazaporphyrin dye mixture which exhibits light absorption over a spectrum range of about 660-850 nm, and provides a process for production of the dye mixture.An invention dye mixture has utility in optical recording media, or as a nonlinear optical component in optical light switch or light modulator devices.Illustrative of an invention dye mixture is a blend of dye constituents respectively having varying combinations of phthalocyanine and naphthalocyanine entities in the macrocyclic structures.
    Type: Grant
    Filed: April 4, 1989
    Date of Patent: February 11, 1992
    Assignee: Hoechst Celanese Corp.
    Inventors: James R. Sounik, Jacquelyn Popolo
  • Patent number: 5073295
    Abstract: There are disclosed coated active substances and a process for the preparation thereof, wherein said active substances are dyes, fluorescent whitening agents, photoactivators and/or textile microbicides, if appropriate together with extenders, dispersants, buffers, stabilizers and/or other auxiliaries.
    Type: Grant
    Filed: July 3, 1990
    Date of Patent: December 17, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Beat Bruttel, Petr Kvita
  • Patent number: 5068339
    Abstract: Triggerable dioxetanes with a fluorescent molecule containing group bonded or tethered in the dioxetane so as to produce fluorescence from the group are described. The compounds are useful in immunoassays and in probes using enzymes or other chemicals for triggering the dioxetanes to produce light from the flurorescent molecule in the group as a signal.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: November 26, 1991
    Assignee: Board of Governors of Wayne State University
    Inventors: Arthur P. Schaap, Hashem Akhavan-Jaffi
  • Patent number: 5015735
    Abstract: 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: Grant
    Filed: December 4, 1989
    Date of Patent: May 14, 1991
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Yusaku Ide, Koji Nakamura, Shigeki Kato