Processes Of Halogenating The Phthalocyanine Ring System Patents (Class 540/138)
  • 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: 6794504
    Abstract: Incipiently chlorinated copper phthalocyanine pigments having a chlorine content of from 10 to 40% by weight and a dispersion harshness ≦10 in LDPE are useful for coloring plastics.
    Type: Grant
    Filed: September 27, 2002
    Date of Patent: September 21, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Ingo Klopp, Josef Hetzenegger, Peter Böttcher
  • Patent number: 5475103
    Abstract: A process for the production of a halogenated phthalocyanine, in which a solvent can be easily recovered and the halogenated phthalocyanine has reduced residual metal amount, the process comprising forming a complex of aluminum chloride and phthalocyanine in sulfonyl chloride and then halogenating the phthalocyanine.
    Type: Grant
    Filed: November 30, 1994
    Date of Patent: December 12, 1995
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventor: Yoshiyuki Nonaka
  • Patent number: 5428153
    Abstract: A process for the production of a halogenated phthalocyanine, in which a solvent can be easily recovered and the produced halogenated phthalocyanine has a reduced residual metal amount, the process comprising forming a complex of aluminum chloride and phthalocyanine in a halogenated hydrocarbon and then halogenating the phthalocyanine.
    Type: Grant
    Filed: November 30, 1994
    Date of Patent: June 27, 1995
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventor: Yoshiyuki Nonaka
  • Patent number: 5387678
    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: June 3, 1993
    Date of Patent: February 7, 1995
    Assignees: Mitsui Toatsu Chemicals, Incorporated, Yamamoto Chemicals, Incorporated
    Inventors: Hisato Itoh, Takahisa Oguchi, Shin Aihara
  • Patent number: 5350843
    Abstract: A method for preparing a mixture of the halogenated alkoxyphthalocyanines represented by the formula (8) which comprises the step of reacting alkoxyphthalocyanines represented by the formula (7) and a mixture thereof with a halogenating agent in a mixed solvent of an organic solvent and water.
    Type: Grant
    Filed: July 6, 1992
    Date of Patent: September 27, 1994
    Assignees: Mitsui Toatsu Chemicals, Incorporated, Yamamoto Chemicals, Incorporated
    Inventors: Hisato Itoh, Takahisa Oguchi, Shin Aihara, Kenichi Sugimoto
  • Patent number: 5286855
    Abstract: A process for producing a polyhalogenated phthalocyanine containing not more than 0.02 part by weight of water-insoluble inorganic impurities derived from aluminum chloride per 100 parts by weight of phthalocyanine before halogenation, which comprises the following steps A, B and C;step A of halogenating phthalocyanine in titanium tetrachloride in the presence of aluminum chloride,step B of evaporating titanium tetrachloride and sublimating aluminum chloride by heating the halogenation reaction mixture, thereby recovering aluminum chloride as a mixture with titanium tetrachloride and obtaining a polyhalogenated phthalocyanine, andstep C of recycling aluminum chloride isolated from the mixture with titanium tetrachloride or said mixture to the step A.
    Type: Grant
    Filed: November 7, 1991
    Date of Patent: February 15, 1994
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Yoshiyuki Nonaka, Junichi Tsuchida, Masami Shirao, Michichika Hikosaka
  • Patent number: 5223027
    Abstract: A polyhalogenated phthalocyanine obtained by halogenation of phthalocyanine in the presence of aluminum chloride and contains not more than 0.02 part by weight, per 100 parts by weight of the phthalocyanine before the halogenation, of water-insoluble inorganic impurities derived from the aluminum chloride contributes to improvement of a printing ink in form plate abrasion properties.
    Type: Grant
    Filed: October 8, 1991
    Date of Patent: June 29, 1993
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Yoshiyuki Nonaka, Junichi Tsuchida, Masami Shirao, Michichika Hikosaka
  • Patent number: 5153313
    Abstract: A process for the preparation of phthalocyanine composites which comprises adding a metal free phthalocyanine, a metal phthalocyanine, a metalloxy phthalocyanine or mixtures thereof to a solution of trifluoroacetic acid and a monohaloalkane; adding to the resulting mixture a titanyl phthalocyanine; adding the resulting solution to a mixture that will enable precipitation of said composite, and recovering the phthalocyanine composite precipitated product.
    Type: Grant
    Filed: June 4, 1990
    Date of Patent: October 6, 1992
    Assignee: Xerox Corporation
    Inventors: Peter M. Kazmaier, Hai-Yen T. Tran, James M. Duff, James D. Mayo, Gordon K. Hamer, Terry L. Bluhm, Cheng K. Hsiao
  • 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
  • Patent number: 4977068
    Abstract: Provided is a novel aromatic ether capped naphthalocyanine compound containing a central hetero atom having a siloxy group substituent off of said hetero atom, with said siloxy substituent having the formula--OSiR.sub.1 R.sub.2 --ZArwhereinR.sub.1 and R.sub.2 can be the same or different, and can be alkyl having from 1 to about 18 carbons; aryl having from 6 to 10 carbons; cycloalkyl having at least 4 carbons or alkoxy having at least 3 carbons,Z is O or S, andAr is an aromatic moiety.Also provided is a process for preparing a naphthalocyanine compound containing a central hetero atom having a siloxy group substituent off of said hetero atom, with said siloxy group containing a terminal ether function, which process comprises reacting in the presence of a nucleophile in a moisture free environment(i) a naphthalocyanine dihydroxy compound,(ii) a compound of the formula SiR.sub.1 R.sub.2 L.sub.2, wherein R.sub.1 and R.sub.
    Type: Grant
    Filed: March 9, 1990
    Date of Patent: December 11, 1990
    Assignee: Hoechst Celanese Corp.
    Inventor: Palaiyur S. Kalyanaraman
  • Patent number: 4948884
    Abstract: Provided according to this invention is a process for the halogenation of copper phthalocyanine in titanium tetrachloride in the presence of aluminum chloride, which comprises preliminarily stirring both a part or all of the aluminum chloride and the copper phthalocyanine in titanium tetrachloride at not less than 50.degree. C. and carrying out the halogenation reaction, provided that when the part of the aluminum chloride is added for the preliminary stirring, the remaining portion of the aluminum chloride is added during the halogenation reaction.
    Type: Grant
    Filed: May 16, 1989
    Date of Patent: August 14, 1990
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Yoshiyuki Nonaka, Junichi Tsuchida, Masami Shirao, Toshiro Notoji, Michichika Hikosaka
  • Patent number: 4879380
    Abstract: A polyhalogenated pigment crude is combined with a heterocyclic organic liquid in which the pigment is only "slightly stable", and the resulting mixture is mixed under high shear conditions to produce a pigmentary product.
    Type: Grant
    Filed: May 5, 1988
    Date of Patent: November 7, 1989
    Assignee: BASF Corp.
    Inventors: John Henry Banties, Thomas Edward Donegan
  • Patent number: 4789739
    Abstract: Polyhalocopper phthalocyanine pigments of high color strength are prepared by recrystallizing the finely divided agglomerated crude pigment in a heterogeneous aqueous organic phase at elevated temperatures by a process in which the aqueous organic phase used is a heterogeneous mixture of an aliphatic ketone having a total of 3 to 9 carbon atoms and water. The process gives the pigments in the form of spherical granules which are dust-free or have a low dust content. The pigments give deep, brilliant colorations of pure hues.
    Type: Grant
    Filed: October 23, 1987
    Date of Patent: December 6, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Joachim Kranz, Karl Schmeidl
  • Patent number: 4680387
    Abstract: Finely divided, agglomerated crude polyhalo-copper phthalocyanine is recrystallized (conditioned) by heating the crude pigment with benzoic acid, toluic acid, ethylbenzoic acid or a mixture of these, in the presence of water, at from 80.degree. to 130.degree. C.The resulting polyhalo-copper phthalocyanine pigments are readily dispersible and of high color strength, and pigmentary forms ranging from transparent to high-hiding can be obtained in a selective manner.The carboxylic acids used as conditioning media can readily be recovered by acidifying the mother liquor.
    Type: Grant
    Filed: November 15, 1985
    Date of Patent: July 14, 1987
    Assignee: BASF Aktiengesellschaft
    Inventor: Joachim Kranz