Specified Crystalline Form Or Processes Of Milling (e.g., Alpha Crystalline Form, Ball Milling, Acid Milling, Etc.) Patents (Class 540/141)
  • Patent number: 9835961
    Abstract: Provided is an excellent phthalocyanine crystal having high sensitivity and little fluctuation in sensitivity for a humidity change in a use environment and applicable to the martial for solar battery, electronic paper, electrophotographic photoreceptor, etc. Namely, phthalocyanine crystal obtained by bringing a phthalocyanine crystal precursor into contact with an aromatic aldehyde compound to convert the crystal form. Also, provided is an electrophotographic photoreceptor that not only exhibits high sensitivity but also has little fluctuation in sensitivity for a humidity change in a use environment. Further, provided is an electrophotographic photoreceptor cartridge and an image-forming device, both of which can produce a stable quality images for a humidity change in a use environment by using the electrophotographic photoreceptor.
    Type: Grant
    Filed: October 26, 2015
    Date of Patent: December 5, 2017
    Assignee: MITSUBISHI CHEMICAL CORPORATION
    Inventors: Mitsuo Wada, Kazutaka Ida, Teruyuki Mitsumori, Hiroaki Takamura, Tadashi Mizushima
  • Patent number: 9296899
    Abstract: Provided is an excellent phthalocyanine crystal having high sensitivity and little fluctuation in sensitivity for a humidity change in a use environment and applicable to the martial for solar battery, electronic paper, electrophotographic photoreceptor, etc. Namely, phthalocyanine crystal obtained by bringing a phthalocyanine crystal precursor into contact with an aromatic aldehyde compound to convert the crystal form. Also, provided is an electrophotographic photoreceptor that not only exhibits high sensitivity but also has little fluctuation in sensitivity for a humidity change in a use environment. Further, provided is an electrophotographic photoreceptor cartridge and an image-forming device, both of which can produce a stable quality images for a humidity change in a use environment by using the electrophotographic photoreceptor.
    Type: Grant
    Filed: March 20, 2007
    Date of Patent: March 29, 2016
    Assignee: MITSUBISHI CHEMICAL CORPORATION
    Inventors: Mitsuo Wada, Kazutaka Ida, Teruyuki Mitsumori, Hiroaki Takamura, Tadashi Mizushima
  • Patent number: 9141007
    Abstract: Provided is a monolayer type photoconductor superior in sensitivity characteristics that allows reliable production by easy confirmation of the sensitivity characteristics, and an image forming device using such a monolayer type photoconductor. A monolayer type photoconductor including a base body and a single photo sensitive layer formed on the base body, the single photo sensitive layer containing a charge generating agent, a hole transfer agent, an electron transfer agent and a binding resin, wherein a maximum absorption wavelength (?max) of the photo sensitive layer is set to a value of below 850 nm and an absorbance (A850) of light at a wavelength of 850 nm per unit thickness of the photo sensitive layer is set to a value of 0.05 ?m?1 or less.
    Type: Grant
    Filed: March 13, 2008
    Date of Patent: September 22, 2015
    Assignee: Kyocera Mita Corporation
    Inventors: Kazunari Hamasaki, Yuko Iwashita, Daisuke Kuboshima, Keiji Maruo, Shiho Kuboshima
  • Publication number: 20140371192
    Abstract: The present invention relates to alpha-form zinc-phthalocyanine nanowires (ZnPc NWs) having enhanced water solubility and water dispersibility, to a composite of an alpha-form zinc-phthalocyanine nanowire/phenothiazine, to a method for preparing same, and to a photosensitizer including same or a pharmaceutical composition including same for preventing or treating cancers. Since the alpha-form zinc-phthalocyanine nanowires or the composite of alpha-form zinc-phthalocyanine nanowire/phenothiazine according to the present invention exhibit dual traits, i.e., photothermal and photodynamic traits in single molecules, they are very useful for the development of a multifunctional molecular system and can also be usefully applied to light therapy of cancers due to their good light therapeutic effects.
    Type: Application
    Filed: August 30, 2012
    Publication date: December 18, 2014
    Applicant: POHANG UNIVERSITY OF SCIENCE AND TECHNOLOGY INDUSTRYACADEMY COOPERATION CORPS
    Inventors: Hee Cheul Choi, Hye Kyung Moon, Sang Ho Lee
  • Publication number: 20140179915
    Abstract: Provided are methods for preparing a phthalocyanine pigment in high yield that eliminate the need to add a heavy metal catalyst. The resulting pigmentary phthalocyanine products thus contain no or only trace amounts of heavy metal impurities. The provided methods produce phthalocyanine pigments that can be used in any application that utilizes phthalocyanine pigments, such as in dispersions, printing inks, paints, plastics and coatings.
    Type: Application
    Filed: January 22, 2014
    Publication date: June 26, 2014
    Applicant: Sun Chemical Corporation
    Inventors: Norman W. Smith, Paul A. Merchak
  • Publication number: 20140054510
    Abstract: Oxotitanium phthalocyanine nanoparticles in the crystal form of phase-Y (Y-TiOPc) having particle diameters of 2˜4 nm, preparation, and applications thereof are disclosed. The preparation method comprises the following steps: mixing a concentrated sulfuric acid solution of TiOPc with water or dilute sulfuric acid, or water or dilute sulfuric acid with a surfactant dissolved therein, or an aqueous solution of a low molecular weight organic compound to form a suspension or hydrosol; adding into the resulting suspension or hydrosol chlorinated hydrocarbons to extract TiOPc into an organic phase, so as to form a colloidal solution of Y-TiOPc nanoparticles; and then, washing and drying the above nanoparticles to give rise to a powder of the Y-TiOPc nanoparticles. Such a nanoparticle powder can disperse in chlorinated hydrocarbons to form stable colloidal solutions, thereby providing an alternative approach for solving the problem of poor dispersibility for Y-type TiOPc.
    Type: Application
    Filed: March 5, 2012
    Publication date: February 27, 2014
    Inventors: Yuan Wang, Dejian Liang, Wenlian Peng
  • Patent number: 8563204
    Abstract: A photoconductor containing an optional supporting substrate, a photogenerating layer, and at least one charge transport layer comprised of at least one charge transport component, and wherein the photogenerating layer contains a hydroxygallium phthalocyanine, a hydroxyaluminum phthalocyanine, a polymeric binder, and a silanol.
    Type: Grant
    Filed: June 29, 2010
    Date of Patent: October 22, 2013
    Assignee: Xerox Corporation
    Inventor: Jin Wu
  • Publication number: 20130137025
    Abstract: Provided is an electrophotographic photosensitive member including a support and a photosensitive layer formed on the support, in which the photosensitive layer includes a phthalocyanine crystal containing a compound satisfying the following formulae (A) and (B) in itself: 8.9??P?10.7 (A) and ?3.2?L??1.5 (B) (in the formula (A), ?P represents a polar term of Hansen Solubility Parameters, and in the formula (B), L represents an energy level (eV) of an LUMO (lowest unoccupied molecular orbital) obtained as a result of structural optimization calculation based on density functional calculation B3LYP/6-31G).
    Type: Application
    Filed: November 29, 2012
    Publication date: May 30, 2013
    Applicant: CANON KABUSHIKI KAISHA
    Inventor: CANON KABUSHIKI KAISHA
  • Publication number: 20130137032
    Abstract: Provided is a method of producing an electrophotographic photosensitive member having improved sensitivity and capable of outputting an image having less image defects due to a ghost phenomenon not only under a normal-temperature, normal-humidity environment but also under a low-temperature, low-humidity environment as a particularly severe condition. The method of producing a gallium phthalocyanine crystal includes subjecting a gallium phthalocyanine and a specific amine compound, which are added to a solvent, to a milling treatment to perform crystal transformation of the gallium phthalocyanine. In addition, the gallium phthalocyanine crystal is used in the photosensitive layer of the electrophotographic photosensitive member.
    Type: Application
    Filed: November 29, 2012
    Publication date: May 30, 2013
    Applicant: CANON KABUSHIKI KAISHA
    Inventor: CANON KABUSHIKI KAISHA
  • Publication number: 20130071664
    Abstract: Disclosed are: copper phthalocyanine pigments which each contain at least one kind of copper phthalocyanine microparticles that has high spectral characteristics and that is in a crystal form other than ?-form; and processes for the production of the copper phthalocyanine microparticles. Provided are: a copper phthalocyanine pigment which contains at least one kind of copper phthalocyanine microparticles that is in a crystal form other than ?-form and that exhibits, in a region of 380 nm to 780 nm, an absorption spectrum shape extremely similar to that of ?-form copper phthalocyanine microparticles; and a process for the production of the copper phthalocyanine microparticles.
    Type: Application
    Filed: March 4, 2011
    Publication date: March 21, 2013
    Applicant: M. TECHNIQUE CO., LTD.
    Inventors: Masaki Maekawa, Daisuke Honda, Masakazu Enomura
  • Publication number: 20120322998
    Abstract: A gallium phthalocyanine crystal has a peak of spectral absorption spectrum within a wavelength range of from about 760 nm to about 773 nm or within a wavelength range of from about 790 nm to about 809 nm.
    Type: Application
    Filed: August 9, 2012
    Publication date: December 20, 2012
    Applicant: FUJI XEROX CO., LTD.
    Inventors: Kazuya HONGO, Tetsuo Ohta, Akira Hirano
  • Publication number: 20120296082
    Abstract: The invention provides an oxo-titanylphthalocyanine crystal which is stable, is superior in dispersibility in a photoreceptive layer and efficiently contributes to improvements in sensitivity and charge retention rate of an electophotographic photoreceptor when it is used as a charge generating agent, a method for producing the oxo-titanylphthalocyanine crystal, and an electrophotographic photoreceptor the oxo-titanylphthalocyanine crystal has predetermined optical characteristics and thermal properties and is produced by a production method including the following steps (a) to (d): (a) a step of dissolving a crude oxo-titanylphthalocyanine crystal in an acid to obtain an oxo-titanylphthalocyanine solution; (b) a step of adding the oxo-titanylphthalocyanine solution dropwise in a poor solvent to obtain a wet cake; (c) a step of washing the wet cake with an alcohol having 1 to 4 carbon atoms; and (d) a step of stirring the washed wet cake under heating in a nonaqueous solvent to obtain an oxo-titanylphthalocya
    Type: Application
    Filed: July 11, 2012
    Publication date: November 22, 2012
    Inventors: Daisuke KUBOSHIMA, Jun AZUMA, Yoshio INAGAKI, Junichiro OTSUBO, Keiji MARUO
  • Patent number: 8242261
    Abstract: The invention provides an oxo-titanylphthalocyanine crystal which is stable, is superior in dispersibility in a photoreceptive layer and efficiently contributes to improvements in sensitivity and charge retention rate of an electrophotographic photoreceptor when it is used as a charge generating agent, a method for producing the oxo-titanylphthalocyanine crystal, and an electrophotographic photoreceptor.
    Type: Grant
    Filed: October 1, 2010
    Date of Patent: August 14, 2012
    Assignee: Kyocera Mita Corporation
    Inventors: Daisuke Kuboshima, Jun Azuma, Yoshio Inagaki, Junichiro Otsubo, Keiji Maruo
  • Patent number: 8206502
    Abstract: The invention is directed to mixtures of PcTiO and a minor amount of another, substituted titanyl phthalocyanine and the synthesis of mixtures of PcTiO and a minor amount of another, substituted titanyl phthalocyanine. The invention is further directed towards milled pigment compositions of such mixtures, and to use of such milled pigment compositions in an electrophotographic element.
    Type: Grant
    Filed: December 15, 2008
    Date of Patent: June 26, 2012
    Assignee: Eastman Kodak Company
    Inventor: William T. Gruenbaum
  • Patent number: 8110038
    Abstract: The present invention provides a mixed crystal having absorption properties that are excellent for color reproducibility as a blue pigment, and including a compound represented by the following Formula (I) and a compound represented by the following Formula (II), and a colored pigment dispersion composition including the mixed crystal and a medium. In Formula (I), X represents —SO—Z, —SO2—Z, —SO2NR1R2, —SO3R1, —CONR1R2 or —CO2R1; Z, R1 and R2 each independently represent an alkyl group, an aryl group, a heterocyclic group or the like; Y represents a monovalent substituent; M1 represents a hydrogen atom, a metal element or the like; and a and b are integers from 0 to 16 and satisfy the relationship of 0?a+b?16. In Formula (II), G1 to G4 and Q1 to Q4 each independently represent a carbon atom or a nitrogen atom, and A1 to A4 each independently represent a group of atoms necessary for forming an aromatic ring or heterocycle with the respective G1 to G4 and Q1 to Q4.
    Type: Grant
    Filed: March 27, 2009
    Date of Patent: February 7, 2012
    Assignee: Fujifilm Corporation
    Inventors: Shigeaki Tanaka, Keiichi Tateishi
  • Patent number: 8053570
    Abstract: The present invention relates to a method for producing an ?-form titanylphthalocyanine represented by the formula (1): which has a peak at a Bragg angle (2?±0.2°) in X-ray diffraction spectrum with CuK ?-ray: 7.5°, 10.2°, 12.6°, 13.2°, 15.1°, 16.3°, 17.3°, 18.3°, 22.5°, 24.2°, 25.3° and 28.6°, wherein the method includes steps of: (I) subjecting a crude titanylphthalocyanine having an ?-form polymorph to an acid pasting treatment, and then filtering and washing with water to give a water-containing wet cake, and then subjecting the wet cake to drying and crushing to give a low crystalline titanylphthalocyanine; (II) adding a dispersing aid to the low crystalline titanylphthalocyanine and dispersing at room temperature, in DMF, to prepare a polymorph; and (III) filtering, washing, and drying under a reduced pressure.
    Type: Grant
    Filed: July 22, 2008
    Date of Patent: November 8, 2011
    Assignee: Orient Chemical Industries, Ltd.
    Inventors: Kenji Takaki, Yasuhiro Yamasaki
  • Patent number: 7998650
    Abstract: Disclosed herein is a method for preparing oxytitanium phthalocyanine as a charge generating material. The method comprises the steps of mixing 30˜100 wt % sulfuric acid and an oxytitanium phthalocyanine crude in a mixing ratio between 100:1 and 1:1, homogeneously grinding the mixture in a wet grinder filled with zirconia or glass beads as grinding media at ?20° C.˜60° C. for 0.1˜24 hours, and removing the grinding media from the ground mixture using a solvent. According to the method, oxytitanium phthalocyanine usable as a high-quality charge generating material can be prepared without the use of expensive and difficult-to-handle reactants, such as trifluoroacetic acid and pentafluoropropionic acid. Further disclosed is an oxytitanium phthalocyanine charge generating material prepared by the method.
    Type: Grant
    Filed: October 7, 2004
    Date of Patent: August 16, 2011
    Assignee: PHTALOS Co., Ltd.
    Inventors: Ki Suck Jung, Jong Ho Kwon, Seong Soo Park, Jun Sik Shin, Woo Ho Son, Seung Wook Song
  • Publication number: 20110177337
    Abstract: Disclosed is a copper phthalocyanine pigment comprising copper phthalocyanine that is in an ?-type crystal form and is superior in properties to ?-type copper phthalocyanine under specific conditions. Also disclosed is a process for producing copper phthalocyanine fine particles. The copper phthalocyanine pigment comprises copper phthalocyanine that is in an ?-type crystal form and exhibits a transmission spectrum at 380 to 780 nm that has a highest transmittance wavelength (?max) of less than 478 nm.
    Type: Application
    Filed: September 29, 2009
    Publication date: July 21, 2011
    Inventor: Masakazu Enomura
  • Patent number: 7981581
    Abstract: A phthalocyanine composite with high sensitivity and low environmental dependence is provided. It comprises both at least one phthalocyanine compound expressed by general formula (1) and at least one phthalocyanine compound expressed by general formula (2): where, in the general formulae (1) and (2), M1 represents at least one arbitrary atom or atomic group that is capable of binding to a phthalocyanine, M2 represents an atom, or an atomic group containing an atom, selected from the second and subsequent periods of the periodic table and capable of binding to a phthalocyanine, M1 and M2 being different in kind from each other, X1-X4 represent, independently of each other, a halogen atom, and a, b, c, and d represent, independently of each other, an integer between 0 and 4 and satisfy a+b+c+d?1.
    Type: Grant
    Filed: March 4, 2005
    Date of Patent: July 19, 2011
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Mitsuo Wada, Kazutaka Ida, Akiteru Fujii
  • Publication number: 20110087020
    Abstract: Processes for making photosensitive organic pigments for use in imaging members, specifically processes for making a photosensitive phthalocyanine pigments having a specific crystal form, comprising dissolving the pigment in a mixture of a haloacetic acid and alkylene halide to form a solution, precipitating the pigment by adding the solution to a non-solvent system, the solution comprised of one or more organic solvents and a small amount of water, wherein the amount of water controls the crystal form of the pigment, followed by a treatment with a halobenzene to obtain a highly photosensitive second crystal form of the pigment.
    Type: Application
    Filed: December 14, 2010
    Publication date: April 14, 2011
    Applicant: XEROX CORPORATION
    Inventors: George Liebermann, Marko Saban, Sandra Gardner, Cuong Vong
  • Patent number: 7905952
    Abstract: The invention pertains to pigment compositions comprising from 70 to 93%, preferably from 81 to 93%, of e copper phthalocyanine, from to 18% of an aminomethyl-substituted phthalocyanine, from 2 to 15% of an ammonium sulfonato phthalocyanine and less than 2% of other phthalocyanine compounds, preferably 5 made by wet-milling a mixture of a copper phthalocyanine and e copper phthalocyanine together with the aminomethyl-substituted phthalocyanine and a milling aid in an organic liquid and adding the ammonium sulfonato phthalocyanine before the milling aid and the organic liquid are separated from the wet-milled mixture.
    Type: Grant
    Filed: January 28, 2008
    Date of Patent: March 15, 2011
    Assignee: BASF SE
    Inventors: HyeonKook Lee, JangWon Jung, Takashi Deno, Masaki Ohwa
  • Patent number: 7794536
    Abstract: A method is provided for pigment dispersion. The method includes preparing a solution in which the pigment is dissolved in an organic acid, preparing a reaction liquid capable of decreasing the solubility of the pigment in the solution, and mixing the solution and the reaction liquid in the presence of an additive represented by a General Formula (1) below, CmH2m+1(OCH2CH2)nOH??(1) wherein m is an integer higher than 14 and lower than 18, and n is an integer equal to or higher than 15 and equal to or lower than 25.
    Type: Grant
    Filed: October 20, 2008
    Date of Patent: September 14, 2010
    Assignee: Canon Kabushiki Kaisha
    Inventors: Takayuki Teshima, Tetsuo Hino
  • Publication number: 20100081073
    Abstract: According to the present invention, a titanyl phthalocyanin crystal excellent in storage stability in organic solvents, a method for preparing the same and an electrophotographic photoconductor using the same are provided. In the titanyl phthalocyanin crystal, the method for preparing such a titanyl phthalocyanin crystal and the electrophotographic photoconductor using the same, the titanyl phthalocyanin crystal is characterized by having the maximum peak at a Bragg angle 2 ?±0.2°=27.2° in a CuK? characteristic X-ray diffraction spectrum and one peak within the range of 270 to 400° C. other than a peak accompanied by the vaporization of adsorbed water in a differential scanning calorimetric analysis.
    Type: Application
    Filed: October 29, 2009
    Publication date: April 1, 2010
    Inventors: Junichiro Otsubo, Jun Azuma
  • Patent number: 7682762
    Abstract: Processes for making photosensitive organic pigments for use in imaging members, specifically processes for making photosensitive phthalocyanine pigments having a specific nanocrystal form. Embodiments include a copper phthalocyanine nanocrystal with good charge generation for use in the formulation of a charge generating layer and narrow particle size distribution.
    Type: Grant
    Filed: May 8, 2007
    Date of Patent: March 23, 2010
    Assignee: Xerox Corporation
    Inventors: Daniel V. Levy, Liang-bih Lin, Jin Wu
  • Patent number: 7585363
    Abstract: A method for preparing a nanodispersion comprising the steps of: (i) introducing into a milling apparatus a solid fluorinated phthalocycanine pigment according to Formula (I): Wherein M is a metal cation chosen from Groups 1b, 2b, 2a or 3a of the Periodic Table of the Elements; R is fluorine, a perfluoroalkyl or a perfluoroaryl group; z is 1 to 4; L is an anionic ligand; and n is 0 or 1 such that the overall charge on the molecular unit is neutral; followed by milling with agitation the solid fluorinated phthalocyanine in an organic solvent into a suspension of particles so that at least 80 volume % of the particles have a particle size of less than 100 nm.
    Type: Grant
    Filed: October 29, 2008
    Date of Patent: September 8, 2009
    Assignee: Eastman Kodak Company
    Inventors: Tommie L. Royster, Jr., Marina E. Kondakova, Peter G. Bessey
  • Patent number: 7569106
    Abstract: The invention relates to a method for producing an aqueous suspension of pure-phase ?-copper phtalocyanine blue pigment using an agitator ball mill. According to said method: a) in a preparatory step, a phthalocyanine crude blue is suspended by means of a dissolver in an aqueous medium, said aqueous medium containing in particular lipophilic substances, which are similar to binding agents and are compatible with the final application medium and crystalline-phase controlling and/or pigment-surface conditioning compounds; b) said aqueous suspension of the phthalocyanine crude blue is ground in an agitator ball mill to form a suspension of a ?-phtalocyanine blue pigment. The aqueous suspension thus obtained is characterized in that it contains a high-grade ?-phtalocyanine blue pigment for producing a conditioned ?-phtalocyanine blue pigment. The advantage is that said suspension can also be directly converted into a colour concentrate, in particular by means of a flushing and kneading method.
    Type: Grant
    Filed: June 16, 2005
    Date of Patent: August 4, 2009
    Assignee: Colour Ltd.
    Inventors: Rainer Heubach, Dieter Lieske
  • Publication number: 20090068576
    Abstract: A gallium phthalocyanine crystal has a peak of spectral absorption spectrum within a wavelength range of from about 760 nm to about 773 nm or within a wavelength range of from about 790 nm to about 809 nm.
    Type: Application
    Filed: March 14, 2008
    Publication date: March 12, 2009
    Applicant: FUJI XEROX CO., LTD.
    Inventors: Kazuya Hongo, Tetsuo Ohta, Akira Hirano
  • Patent number: 7462711
    Abstract: An object of the present invention is to provide a novel ?-oxo bridged heterometal phthalocyanine compound, and a production method such that the ?-oxo bridged heterometal phthalocyanine compound is obtained simply, selectively and with high yield. The ?-oxo bridged heterometal phthalocyanine compound has a structure in which the central metal atom (M1) in a metal phthalocyanine including M1 as central metal thereof is oxo-bridged with the central metal M2 in a metal phthalocyanine including M2 as central metal thereof.
    Type: Grant
    Filed: June 9, 2003
    Date of Patent: December 9, 2008
    Assignee: Orient Chemical Industries, Ltd.
    Inventors: Kenji Takaki, Yasuhiro Yamasaki
  • Patent number: 7459016
    Abstract: A method for the production of a phthalocyanine pigment preparation includes finely distributing a crude phthalocyanine pigment by dry milling, wet milling, salt kneading, acid pasting or acid swelling to give a pre-pigment, the pre-pigment is subjected to a finishing treatment in a mixture of water and an organic solvent at alkaline pH, increased temperature and in the presence of at least one pigment dispersant from the group of phthalocyanine sulphonic acids, phthalocyanine carboxylic acids, phthalocyanine sulphonate salts, phthalocyanine carboxylate salts and phthalocyanine suiphonamides.
    Type: Grant
    Filed: November 27, 2003
    Date of Patent: December 2, 2008
    Assignee: Clariant Produkte (Deutschland) GmbH
    Inventors: Klaus Brychcy, Joachim Weber, Heidrun Mehler
  • Publication number: 20080286008
    Abstract: A titanylphthalocyanine crystal having an X-ray diffraction spectrum having plural diffraction peaks and a primary particle diameter not greater than 0.2 ?m, wherein a maximum diffraction peak is observed at a Bragg (2 ?) angle of 27.2±0.2°; main peaks are observed at 9.4°, 9.6° and 24.0°; and a minimum diffraction peak is observed at 7.3°; and preferably no diffraction peak is observed at an angle greater than 7.3° and less than 9.4° when a specific X-ray of CuK? having a wavelength of 1.542 ? irradiates the titanylphthalocyanine crystal.
    Type: Application
    Filed: July 16, 2008
    Publication date: November 20, 2008
    Inventor: Tatsuya NIIMI
  • Patent number: 7329315
    Abstract: Phthalocyanine blue pigments and pigment dispersions for water-borne inks and coatings are described. The pigments are produced by dry milling phthalocyanine blue and a polymeric dispersant, optionally with inorganic fillers and other additives, to obtain a material with improved coloristic, rheological, and stability properties. The resulting activated crude is then processed directly into water-based pigment dispersion with additives and/or surfactants to facilitate conversion to pigmentary form while maintaining the desirable green and clean shade.
    Type: Grant
    Filed: December 11, 2006
    Date of Patent: February 12, 2008
    Assignee: Sun Chemical Corporation
    Inventors: Stanislav Vilner, Tatiana N. Romanova, Mark Ortalano, George H. Robertson, Russell J. Schwartz
  • Patent number: 7255733
    Abstract: A process for the production of a ? type copper phthalocyanine pigment, comprising dry-milling a crude copper phthalocyanine having a purity of 97 to 100% and a primary crystal diameter of 0.5 to 100 ?m at a temperature of 180 to 50° C., to prepare an ?/? mixed crystal type copper phthalocyanine having an ? ratio of 5 to 35%, and treating the dry-milled product with a water-miscible organic solvent, wherein 0.1 to 20% by weight of at least one compound selected from the group consisting of a compound of the formula (1), a compound of the formula (2) and a compound of the formula (3) is added to the dry-milled product before, during or after the step (B) MePc—{X—(CH2)kNR1R2}n??(1) MePc—(SO3?N+R5R6R7R8)p.
    Type: Grant
    Filed: June 18, 2004
    Date of Patent: August 14, 2007
    Assignee: Toyo Ink Mfg. Co., Ltd.
    Inventors: Osamu Shiromaru, Yusaku Ide, Toshio Oshiba, Takuya Kotani
  • Patent number: 7186490
    Abstract: A titanyl phthalocyanine crystal having an X-ray diffraction spectrum having a plurality of diffraction peaks in which a maximum diffraction peak is observed at a Bragg (2 ?) angle of 27.2°±0.2° and a diffraction peak is observed at a lowest Bragg (2?) angle of 7.3°±0.2° when a specific X-ray of Cu—K? having a wavelength of 1.514 ? irradiates the titanyl phthalocyanine crystal. A photoreceptor having a photosensitive layer including the titanyl phthalocyanine crystal is also provided.
    Type: Grant
    Filed: May 8, 2000
    Date of Patent: March 6, 2007
    Assignee: Ricoh Company, Ltd.
    Inventors: Tatsuya Niimi, Tetsuro Suzuki
  • Patent number: 7169920
    Abstract: Methods for preparing phthalocyanine co-crystals are provided. The phthalocyanine co-crystals include titanyl phthalocyanines and metal free phthalocyanines.
    Type: Grant
    Filed: April 22, 2005
    Date of Patent: January 30, 2007
    Assignee: Xerox Corporation
    Inventors: Liang-Bih Lin, John S. Chambers, Jin Wu, Francisco José López
  • Patent number: 7087747
    Abstract: An object of the present invention is to provide a new ?-oxo bridged heterometal compound, which can make the photo-functional materials to have diversified properties, and a production method such that the ?-oxo bridged heterometal compound is obtained simply, selectively and with high yield. The present invention provides ?-oxo bridged heterometal compounds, NcM1-O-M2Nc, PcM1-O-M2Nc and NcM1-O-M2Pc wherein Nc represents naphthalocyanine, Pc represents phthalocyanine, M1 represents a metal atom which is able to have a valence of up to three, and M2 represents a metal atom which is able to have a valence of four or five.
    Type: Grant
    Filed: November 6, 2003
    Date of Patent: August 8, 2006
    Assignee: Orient Chemical Industries, Ltd.
    Inventors: Yasuhiro Yamasaki, Kenji Takaki
  • Patent number: 7057034
    Abstract: The present invention relates to a novel titanyl phthalocyanine crystal which can prepare a coating solution having excellent storage stability because it satisfies both of the following two characteristics (a) and (b), a method of producing the same, an electrophotosensitive material using the above crystal as an electric charge generating material. (a) The crystal has a maximum peak at a Bragg angle 2?±0.2°=27.2° and has no peak at 7.4° in a CuK? characteristic X-ray diffraction spectrum. (b) The crystal does not have a peak of a change in temperature within a range from 50 to 400° C. except for a peak associated with evaporation of adsorbed water in differential scanning calorimetry.
    Type: Grant
    Filed: August 27, 2003
    Date of Patent: June 6, 2006
    Assignee: Kyocera Mita Corporation
    Inventors: Kazunari Hamasaki, Daisuke Kuboshima, Hisakazu Honma, Jun Azuma, Eiichi Miyamoto
  • Patent number: 7033716
    Abstract: An amorphous mixture consisting essentially of TiOFPc and TiOPc and containing more than 75 weight percent of substantially chlorine-free TiOPc is produced by forming a mixture of crude crystalline TiOFPc and crude crystalline, substantially chlorine-free TiOPc that contains less than 80 weight percent TiOPc, treating the mixture under conditions effective to form a substantially amorphous mixture of TiOFPc and TiOPc containing less than 75 weight percent TiOPc, which is then treated with water, and dried. A further amount of crude crystalline, substantially chlorine-free TiOPc sufficient to form a new mixture containing more than 75 weight percent of substantially chlorine-free TiOPc is added, and the new mixture is converted to a substantially amorphous mixture of TiOFPc and TiOPc. A nanoparticulate cocrystalline composition is obtained by forming a slurry in an organic solvent of the dried substantially amorphous mixture, and wet milling the slurry to form the cocrystalline composition.
    Type: Grant
    Filed: September 4, 2003
    Date of Patent: April 25, 2006
    Assignee: Eastman Kodak Company
    Inventors: Michel F. Molaire, Jeanne E. Kaeding, Theodore Zubil
  • Patent number: 7029810
    Abstract: An electrophotographic image forming apparatus comprising: an electrophotographic photoreceptor comprising: an electroconductive substrate; a charge generation layer; and a charge transport layer in this order, a charger; an irradiator; an image developer; and a transferer applying an electric current not less than 65 ?A to the electrophotographic photoreceptor, wherein the charge generation layer comprises titanylphthalocyanine crystals having a CuK? 1.542 ? X-ray diffraction spectrum having plural diffraction peaks, wherein a maximum diffraction peak is observed at a Bragg (2 ?) angle of 27.2°; main peaks are observed at 9.4°, 9.6° and 24.0°; and a minimum diffraction peak is observed at 7.3°; and no diffraction peak is observed at an angle greater than 7.3° and less than 9.4°, wherein said angles may vary by ±0.2° and the minimum interval where no peak is observed between required peaks at 7.3 and 9.4 is 2.0 degrees absolute or more.
    Type: Grant
    Filed: September 22, 2003
    Date of Patent: April 18, 2006
    Assignee: Ricoh Company, Ltd.
    Inventors: Naohiro Toda, Tatsuya Niimi
  • Patent number: 7026084
    Abstract: In a process for forming an amorphous TiOPc/TiOFPc pigment mixture containing a low concentration of TiOFPc, a mixture containing phthalonitrile and titanium tetrachloride is subjected to reaction conditions effective to form lightly chlorine-substituted crude crystalline Cl—TiOPc. The lightly chlorine-substituted crude crystalline Cl—TiOPc is combined with crude crystalline TiOFPc in a weight ratio from about 75:25 Cl—TiOPc:TiOFPc to about 99.5:0.5 Cl—TiOPc:TiOFPC to form a crude crystalline pigment mixture, which is treated under conditions effective to form a substantially amorphous pigment mixture of Cl—TiOPc and TiOFPc. The substantially amorphous mixture can subsequently be converted to a nanocrystalline Cl—TiOPc/TiOFPc pigment composition containing a low concentration of TiOFPc.
    Type: Grant
    Filed: September 4, 2003
    Date of Patent: April 11, 2006
    Assignee: Eastman Kodak Company
    Inventors: Michel F. Molaire, Jeanne E. Kaeding, Theodore Zubil, Jeffrey R. Murray
  • Patent number: 6949139
    Abstract: In a process for forming an amorphous pigment mixture consisting essentially of TiOPc and TiOFPc and containing more than about 75 weight percent of TiOPc, a mixture of crude crystalline TiOPc and TiOFPc pigments in a weight ratio of at least 75:25 TiOPc:TiOFPc is combined with at least about 5 wt. %, based on the total weight of TiOPc and TiOFPc, of an organic milling aid. The mixture is treated under conditions effective to form a substantially amorphous pigment mixture of TiOPc and TiOFPc. The organic milling aid can be separated from the substantially amorphous pigment mixture, which can be converted to a nanoparticulate cocrystalline TiOPc/TiOFPc composition.
    Type: Grant
    Filed: September 4, 2003
    Date of Patent: September 27, 2005
    Assignee: Eastman Kodak Company
    Inventors: Michel F. Molaire, Louis J. Sorriero
  • Patent number: 6860934
    Abstract: A process for the production of a ? type copper phthalocyanine pigment having an average primary crystal diameter of 80±40 nm and a primary crystal aspect ratio of 2.0±1.0 and having a crystallite diameter of 22±5 nm in the direction perpendicular to a monoclinic ? (200) plane, a crystallite diameter of 27±5 nm in the direction perpendicular to a ? (001) plane and a crystallite diameter of 15±5 nm in the direction perpendicular to a ? (010) plane, which process comprises, dry-milling a crude copper phthalocyanine having a purity of 97 to 100% and a primary crystal diameter of 0.5 to 100 ?m at 180 to 50° C., to prepare an ?/? mixed crystal type copper phthalocyanine having an a ratio of 5 to 35%, and treating the dry-milled product in a water-miscible organic solvent.
    Type: Grant
    Filed: June 10, 2004
    Date of Patent: March 1, 2005
    Assignee: Toyo Ink Mfg. Co., Ltd.
    Inventors: Osamu Shiromaru, Yuusaku Ide, Toshio Oshiba, Takuya Kotani
  • Publication number: 20040260083
    Abstract: A process for the production of a &bgr; type copper phthalocyanine pigment, comprising dry-milling a crude copper phthalocyanine having a purity of 97 to 100% and a primary crystal diameter of 0.5 to 100 &mgr;m at a temperature of 180 to 50° C.
    Type: Application
    Filed: June 18, 2004
    Publication date: December 23, 2004
    Inventors: Osamu Shiromaru, Yusaku Ide, Toshio Oshiba, Takuya Kotani
  • Patent number: 6815132
    Abstract: A crystalline phase of titanyl oxyphthalocyanine, referred to herein as the S-phase, has an internal blend of lattice arrangements is provided by treatment of the gamma-form of titanyl oxyphthalocyanine. The S-phase is a truly new phase, and not a mixture of particles of various phases (e.g., combinations of the beta-phase and the gamma-phase), with internal lattice distributions of atoms and molecules forming a new, non-continuous, non-uniform lattice structure. The x-ray spectrum shows a blend of diffraction peaks, having peaks that have previously been distinctly present only collectively among various crystalline forms of titanyl oxyphthalocyanine, but can now be provided in a single crystalline form. The visible spectra show significant absorption differences. The novel S-form titanyl oxyphthalocyanine is also used in a photoconductor displaying major peaks of Bragg's 2 theta angle to the CuK-alpha characteristic X-ray (wavelength 1.541 Angstrom) at least at 9.5±0.2 degrees, 9.7±0.
    Type: Grant
    Filed: December 24, 2002
    Date of Patent: November 9, 2004
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Jiayi Zhu, Zbigniew Tokarski, James A. Baker, Ronald J. Moudry, David T. Ask, Nusrallah Jubran, Kam W. Law
  • Patent number: 6768006
    Abstract: An electrophotographic photosensitive member exhibiting a high sensitivity and a potential stability on repetitive use and capable of suppressing image defects, such as black spots in a reversal development scheme, is provided. The photosensitive member includes a support, and a phthalocyanine layer formed on the support and a novel phthalocyanine crystal, which comprises a phthalocyanine compound and a substituted or unsubstituted condensed polycyclic hydrocarbon compound.
    Type: Grant
    Filed: August 23, 2002
    Date of Patent: July 27, 2004
    Assignee: Canon Kabushiki Kaisha
    Inventors: Masato Tanaka, Hidetoshi Hirano, Kan Tanabe, Kazue Asakura, Atsushi Fujii
  • Publication number: 20040126686
    Abstract: An electrophotographic image forming apparatus comprising:
    Type: Application
    Filed: September 22, 2003
    Publication date: July 1, 2004
    Inventors: Naohiro Toda, Tatsuya Niimi
  • Publication number: 20040110075
    Abstract: In a process for forming an amorphous TiOPc/TiOFPc pigment mixture containing a low concentration of TiOFPc, a mixture containing phthalonitrile and titanium tetrachloride is subjected to reaction conditions effective to form lightly chlorine-substituted crude crystalline Cl—TiOPc. The lightly chlorine-substituted crude crystalline Cl—TiOPc is combined with crude crystalline TiOFPc in a weight ratio from about 75:25 Cl—TiOPc:TiOFPc to about 99.5:0.5 Cl—TiOPc:TiOFPC to form a crude crystalline pigment mixture, which is treated under conditions effective to form a substantially amorphous pigment mixture of Cl—TiOPc and TiOFPc. The substantially amorphous mixture can subsequently be converted to a nanocrystalline Cl—TiOPc/TiOFPc pigment composition containing a low concentration of TiOFPc.
    Type: Application
    Filed: September 4, 2003
    Publication date: June 10, 2004
    Applicant: NexPress Solutions LLC
    Inventors: Michel F. Molaire, Jeanne E. Kaeding, Theodore Zubil, Jeffrey R. Murray
  • Publication number: 20040106055
    Abstract: In a process for forming an amorphous pigment mixture consisting essentially of TiOPc and TiOFPc and containing more than about 75 weight percent of TiOPc, a mixture of crude crystalline TiOPc and TiOFPc pigments in a weight ratio of at least 75:25 TiOPc:TiOFPc is combined with at least about 5 wt. %, based on the total weight of TiOPc and TiOFPc, of an organic milling aid. The mixture is treated under conditions effective to form a substantially amorphous pigment mixture of TiOPc and TiOFPc. The organic milling aid can be separated from the substantially amorphous pigment mixture, which can be converted to a nanoparticulate cocrystalline TiOPc/TiOFPc composition.
    Type: Application
    Filed: September 4, 2003
    Publication date: June 3, 2004
    Applicants: NexPress Solutions LLC, Heidelberg Digital LLC
    Inventors: Michel F. Molaire, Louis J. Sorriero
  • Publication number: 20040106053
    Abstract: An amorphous mixture consisting essentially of TiOFPc and TiOPc and containing more than 75 weight percent of substantially chlorine-free TiOPc is produced by forming a mixture of crude crystalline TiOFPc and crude crystalline, substantially chlorine-free TiOPc that contains less than 80 weight percent TiOPc, treating the mixture under conditions effective to form a substantially amorphous mixture of TiOFPc and TiOPc containing less than 75 weight percent TiOPc, which is then treated with water, and dried. A further amount of crude crystalline, substantially chlorine-free TiOPc sufficient to form a new mixture containing more than 75 weight percent of substantially chlorine-free TiOPc is added, and the new mixture is converted to a substantially amorphous mixture of TiOFPc and TiOPc. A nanoparticulate cocrystalline composition is obtained by forming a slurry in an organic solvent of the dried substantially amorphous mixture, and wet milling the slurry to form the cocrystalline composition.
    Type: Application
    Filed: September 4, 2003
    Publication date: June 3, 2004
    Applicant: NexPress Solutions LLC
    Inventors: Michel F. Molaire, Jeanne E. Kaeding, Theodore Zubil
  • Publication number: 20040049027
    Abstract: The present invention relates to a novel titanyl phthalocyanine crystal which can prepare a coating solution having excellent storage stability because it satisfies both of the following two characteristics (a) and (b), a method of producing the same, an electrophotosensitive material using the above crystal as an electric charge generating material.
    Type: Application
    Filed: August 27, 2003
    Publication date: March 11, 2004
    Inventors: Kazunari Hamasaki, Daisuke Kuboshima, Hisakazu Honma, Jun Azuma, Eiichi Miyamoto
  • Publication number: 20040033428
    Abstract: A titanylphthalocyanine crystal having an X-ray diffraction spectrum having plural diffraction peaks and a primary particle diameter not greater than 0.2 &mgr;m, wherein a maximum diffraction peak is observed at a Bragg (2&thgr;) angle of 27.2±0.2°; main peaks are observed at 9.4°, 9.6° and 24.0°; and a minimum diffraction peak is observed at 7.3°; and preferably no diffraction peak is observed at an angle greater than 7.3° and less than 9.4° when a specific X-ray of CuK&agr; having a wavelength of 1.542 Å irradiates the titanylphthalocyanine crystal.
    Type: Application
    Filed: June 5, 2003
    Publication date: February 19, 2004
    Inventor: Tatsuya Niimi