Each Benzene Ring Is Bonded Directly To An Azo Group Patents (Class 534/747)
  • Patent number: 6329531
    Abstract: The invention relates to compounds of formula (I): Fm(—A1)(—Bn)(—Wo) wherein F is a colorant-signal molecule with a maximum absorption value ranging from 600-1200 nm; A is a &bgr;-amyloid plaque binding biomolecule; B is a &bgr;-amyloid plaque binding colorant; and W is a &bgr;-amyloid plaque binding hydrophilic low-molecular structural element. The invention also describes the use of these compounds in in vivo an din vitro diagnosis of neurodegenerative diseases such as Alzheimer's disease by means of near infra-red radiation (NIR radiation) as a constrasting agent in fluoresecence and transillumination diagnosis in the NIR range. Diagnostic agents containing said componenets are also disclosed.
    Type: Grant
    Filed: November 18, 1999
    Date of Patent: December 11, 2001
    Assignee: Schering AG
    Inventors: Jonathan Turner, Thomas Dyrks, Wolfhard Semmler, Kai Licha, Bjorn Riefke
  • Patent number: 6303762
    Abstract: Disclosed is a method of producing a disazo pigment, which a coupling reaction is carried out while feeding, into an acidic aqueous solution, a tetrazo aqueous solution containing a tetrazo component of benzidines and a coupler aqueous solution containing a coupling component, wherein the coupling component is a mixture comprising a main component represented by the formula (1): CH3COCH2CONH—X, wherein X represents a phenyl group optionally having one or the same or different plural substituents selected from the group consisting of a methyl group, methoxy group and chlorine atom; a first additional component represented by the formula (2): CH3COCH2CONH—Y, wherein Y represents a phenyl group having a substituent selected from the group consisting of —CONR2 group, —SO2NR2 group and —NHCOR group, and the phenyl group may further have a substituent selected from the group consisting of a methyl group, methoxy group, chlorine atom, —CONR2 group, —SO2NR2 group and —N
    Type: Grant
    Filed: April 6, 2001
    Date of Patent: October 16, 2001
    Assignee: TOYO INK Mfg. Co., Ltd.
    Inventors: Hitoshi Maki, Hideto Noguchi, Kenji Kitamura, Masami Shirao
  • Patent number: 5958128
    Abstract: In the method of manufacturing a disazo pigment according to the present invention, a superior coupling reaction rate during the coupling reaction process makes it possible to manufacture a disazo pigment having superior transparency, brightness, color strength and gloss for the case in which a color strength agent is used. In this method, a coupling reaction is carried out while continuously feeding a coupler aqueous solution comprising a coupler component having the general formula (I) shown below and a tetrazo aqueous solution comprising a benzidine derivative tetrazo component at a molar ratio of 2:0.8.about.0.99 into an acidic aqueous solution held in a batch type mixing vessel. ##STR1## (where each of X, Y, Z independently represents H, CH.sub.3, OCH.sub.
    Type: Grant
    Filed: October 24, 1997
    Date of Patent: September 28, 1999
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Yoshimi Kikuchi, Hitoshi Sugamo
  • Patent number: 5489672
    Abstract: A process for the production of a dis-azo pigment which is excellent in sanitary condition and almost free of a residual coupler component and decomposition products derived from the residual coupler component, and has a reduced aromatic amine content, and a dis-azo pigment produced by the said process, the process comprising the steps of (a) coupling-reacting a solution of a tetrazonium salt of benzidine with a slurry of acetoacetanilide of which the amount is stoichiometrically excess relative to an amount of said tetrazonium salt, to prepare a dis-azo pigment slurry, and (b) adding a halogen to the dis-azo pigment slurry to treat the acetoacetanilide in said slurry.
    Type: Grant
    Filed: October 26, 1994
    Date of Patent: February 6, 1996
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Osamu Shiromaru, Hitoshi Sugamo
  • Patent number: 5194597
    Abstract: The industrial preparation of C.I. Pigment Yellow 81 by conventional coupling methods has the disadvantage that traces of polychlorinated biphenyls are formed in the course of the reaction of the two components.The invention now provides that the addition of quaternary dialkyldiallylammonium compounds during the azo coupling will decisively suppress the PCB-forming secondary reactions during the pigment synthesis.
    Type: Grant
    Filed: April 30, 1991
    Date of Patent: March 16, 1993
    Assignee: Hoechst AG
    Inventor: Wolfgang Rieper
  • Patent number: 5051131
    Abstract: An azo pigment composition which forms a dispersion having high tinting strength and excellent clearness, transparency, fluidity and storage stability, and which is formed from a coupling reaction between a diazo component and a coupler component, and contains a compound represented by formula (I) ##STR1## wherein Q represents a diazo or coupler component moiety, A represents a divalent bonding group selected from a class consisting of --CONR'--, SO.sub.2 NR'--, --CH.sub.2 NH-- and --CH.sub.2 NHCOCH.sub.2 NH-- in which R' represents a hydrogen atom, alkyl group having 1 to 20 carbon atoms or aryl group,each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represents a hydrogen atom, alkyl group having 1 to 20 carbon atoms or alkenyl group having 2 to 20 carbon atoms, and R.sub.3 and R.sub.
    Type: Grant
    Filed: December 12, 1989
    Date of Patent: September 24, 1991
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Takahiro Yuasa, Kenzi Kitamura
  • Patent number: 5034063
    Abstract: A disazo pigment composition which can provide a printing ink having excellent fluidity, gloss and storage stability, and which contains:a disazo pigment obtained by a coupling reaction between a tetrazo compound of dihalogenobenzidine and acetoacetanilides, anda reaction product from a coupling reaction between an acetoacetylation product and a tetrazo compound of dihalogenobenzidine.
    Type: Grant
    Filed: October 4, 1989
    Date of Patent: July 23, 1991
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Yoshie Suzuki, Ataru Chiba, Kenji Kitamura, Akimitsu Mochizuki
  • Patent number: 5021090
    Abstract: Water-based diarylide pigment compositions containing diarylide pigment modified with water-soluble amines. The pigment compositions are useful in both water-based coating and ink compositions.
    Type: Grant
    Filed: May 23, 1989
    Date of Patent: June 4, 1991
    Assignee: Sun Chemical Corporation
    Inventors: Russell J. Schwartz, Manuel Z. Gregorio
  • Patent number: 4981489
    Abstract: Disazo compounds based on 4,4'-diaminodiphenyl compounds contain not less than 50% by weight of a disazo compound of the general formulaA--N.dbd.N--Z--N.dbd.N--B (I)where Z is a radical of an unsubstituted or symmetrically substituted diphenylene, A is a radical of a coupling component of a 1-phenylpyrazolone or of an acetoacetarylide, where the phenyl and the aryl radical is subtsituted by sulfo or carboxyl groups, and B is a radical of a coupling component based on 1-phenylpyrazolone or acetoacetarylide, which are free of sulfo and/or carboxyl groups.The disazo compounds can be obtained by coupling the tetrazotized diamine H.sub.2 N--Z--NH.sub.2 to the coupling component AH containing an acidic group in a medium containing a mineral acid, and then coupling the product to BH in a buffered medium (pH about 4).The novel disazo compounds are suitable as additives to pigments, in particular azo and disazo pigments, for improving the transparency and heat stability of the pigment particles, and the flow behavior.
    Type: Grant
    Filed: October 23, 1989
    Date of Patent: January 1, 1991
    Assignee: BASF Lacke & Farben Aktiengesellschaft
    Inventors: Wolfgang Ruff, Egon Liedek, Gerhard Berger, Hans W. Sonneborn
  • Patent number: 4968352
    Abstract: Diaryl pigments having excellent dried ink transparency and improved process heat stability are prepared by carrying out the coupling of a bisdiazotized substituted 4,4' diaminobiphenyl with acetoacetanilides and/or pyrazolinones in the presence of an added quantity of one or more substituted aromatic amines containing at least one sulfonic or carboxylic acid substituent, or their salts. The pigments exhibit improved tolerance to variations in drying temperatures and to high drying temperatures, and have improved transparency when present in dried ink formulations.
    Type: Grant
    Filed: April 28, 1988
    Date of Patent: November 6, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Boyd A. Keys, John T. Ouderkirk
  • Patent number: 4894094
    Abstract: Disazo compounds based on 4,4'-diaminodiphenyl compounds contain not less than 50% by weight of a disazo compound of the general formulaA--N.dbd.N--Z--N.dbd.N--B (I)where Z is a radical of an unsubstituted of symmetrically substituted diphenylene, A is a radical of a coupling component of a 1-phenylpyrazolone or of an acetoacetarylide, where the phenyl and the aryl radical is substituted by sulfo or carboxyl groups, and B is a radical of a coupling component based on 1-phenylpyrazolone or acetoacetarylide, which are free of sulfo and/or carboxyl groups.The disazo compounds can be obtained by coupling the tetrazotized diamine H.sub.2 N--Z--NH.sub.2 to the coupling component AH containing an acidic group in a medium containing a mineral acid, and then coupling the product to BH in a buffered medium (pH about 4).The novel disazo compounds are suitable as additives to pigments, in particular azo and disazo pigments, for improving the transparency and heat stability of the pigment particles, and the flow behavior.
    Type: Grant
    Filed: August 19, 1987
    Date of Patent: January 16, 1990
    Assignee: Basf Lacke & Farben Aktiengesellschaft
    Inventors: Wolfgang Ruff, Egon Liedek, Gerhard Berger, Hans W. Sonneborn
  • Patent number: 4801702
    Abstract: A process for the preparation and conditioning of organic pigments, which comprises the use of at least one tricyclodecane alcohol or tricyclodecene alcohol.
    Type: Grant
    Filed: October 30, 1986
    Date of Patent: January 31, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Fridolin Babler
  • Patent number: 4780533
    Abstract: A disazo pigment is prepared by coupling the tetrazo compound of 3,3'-dichlorobenzidine with an acetoacetanilide compound which is other than those represented by the below-described general formula (I) and is free of water-soluble groups. In the present invention, about 0.5-50 mole % of the acetoacetanilide compound is replaced by a compound represented by the following general formula (I): ##STR1## wherein R means a methyl, ethyl, propyl or butyl group or a substituted or unsubstituted phenyl group.
    Type: Grant
    Filed: February 9, 1987
    Date of Patent: October 25, 1988
    Assignee: Dainichiseika Color & Chemicals Mfg. Co., Ltd.
    Inventors: Naonori Takami, Tetsuo Fukuda, Takeshi Uehara
  • Patent number: 4767844
    Abstract: An azo lake pigment is obtained by coupling an aromatic diazo component having a sulfonic acid group with a mixture of 2-hydroxy-3-naphthoic acid and a 2-hydroxy-3-naphthoic acid derivative represented by formula [I] ##STR1## wherein R represents a hydrogen atom, a naphthalene residue, a cyclohexyl group, or a group of the formula ##STR2## in which each of X, Y and Z represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, an acetylamino group, a benzoylamino group, a carbomoyl group or a phenylcarbamoyl group, and X and Y together may form a cyclized benzimidazolone, benzthiazole or benzoxazole group,and laking the resulting dye with an alkaline earth metal salt or a manganese salt.
    Type: Grant
    Filed: August 21, 1987
    Date of Patent: August 30, 1988
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Hirohito Ando, Zenji Takada, Shigeto Aoki, Yuko Shigeta
  • Patent number: 4720541
    Abstract: Process for improving the application properties of disazo pigments obtained by coupling bis-diazotized chlorine-substituted 4,4'-diaminobiphenyls with acetoacetylaminobenzenes, which includes adding sulfite ions to the pigment suspension obtained in the coupling and then heating for one half to two hours at 50.degree. to 100.degree. C. The process produces, above all in large scale industrial batches, a product of uniform quality and having acceptable fastness to solvents, overlacquering, migration and bleeding.
    Type: Grant
    Filed: July 6, 1984
    Date of Patent: January 19, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Rieper, Klaus Hunger
  • Patent number: 4664709
    Abstract: This invention is directed to new azoacylacetamide dispersing agents for azo pigments and azo pigment compositions made therefrom. The pigment compositions of this invention comprise a mixture of dispersing agents which are represented below by abbreviated Formula I and pigments which are represented by the abbreviated Formula II, wherein said dispersing agents are present in an amount of 1-25% and said pigments are present in an amount of 99 to 75%: ##STR1## where: A is an aromatic or heterocyclic amino group;B is an aromatic or heterocyclic bisdiazonium group;D is an aliphatic polyamino group containing at least three nitrogen atoms.
    Type: Grant
    Filed: February 25, 1985
    Date of Patent: May 12, 1987
    Assignee: American Hoechst Corporation
    Inventor: Richard Castenson
  • Patent number: 4665163
    Abstract: Diaryl pigments having an excellent stability to heat are obtained by carrying out the coupling of bis-diazotized 3,3'-dichloro-4,4'-diaminobiphenyl with acetoacetanilides in the presence of an added quantity of acetoacetanilides which are monosubstituted or disubstituted in the 3-position or 4-position of the nucleus. As a result of their good heat stability, these pigments are particularly suitable for pigmenting plastics having processing temperatures above 200.degree. C.
    Type: Grant
    Filed: June 23, 1983
    Date of Patent: May 12, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Klaus Hunger, Heinrich Frolich, Hans-Joachim Lenz
  • Patent number: 4602960
    Abstract: A novel modified diarylide pigment contains (a) a pigment which is composed of a tetrazotized benzidine, coupled to an acetoacetarylide and/or a 1-phenyl-3-methylpyrazole-5-one, and (b) a water-soluble component obtained from a symmetric or asymmetric coupling product of a tetrazotized 4,4'-diamino-2,2'-stilbenedisulfonic acid and an acetoacetarylide and/or a 1-phenyl-3-methyl-5-pyrazolone. The novel pigments possess very good color strength, very good gloss characteristics and very good transparency, and exhibit improved printing characteristics, particularly in offset printing inks.
    Type: Grant
    Filed: August 16, 1984
    Date of Patent: July 29, 1986
    Assignee: BASF Farben & Fasern Aktiengesellschaft
    Inventors: Egon Liedek, Wolfgang Ruff, Gerhard Berger, Hans W. Sonneborn, Reinhard Kemper
  • Patent number: 4589921
    Abstract: The invention relates to a process for improving the application properties of Pigment Yellow 13. The crude pigment is heated in an aqueous suspension to temperatures above 100.degree. C. Pigment Yellow 13 thus obtained is particularly suitable for replacing lead-containing chrome yellow pigments of comparable shade.
    Type: Grant
    Filed: June 10, 1985
    Date of Patent: May 20, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Klaus Hunger, Wolfgang Rieper
  • Patent number: 4535151
    Abstract: A process for the wet granulation of organic pigment is disclosed which consists in treating under vigorous agitation an aqueous suspension of pigment with acetic anhydride, propionic anhydride or a mixture thereof. Acetic anhydride is used preferentially. After hydrolysis of the anhydride, besides the granules, an aqueous solution of acid or its corresponding salt, directly saleable or re-usable in the chemical industry, is recovered whereby problems related to the recovery of organic solvents are avoided.
    Type: Grant
    Filed: May 16, 1984
    Date of Patent: August 13, 1985
    Assignee: I.C.I. Francolor S.A.
    Inventor: Pierre L. E. Fournier
  • Patent number: 4515639
    Abstract: Intense azo pigment formulations which have good flow and are readily dispersible are obtained on adding a long-chain aliphatic primary amine and a diamine of the formulaH.sub.2 N--A--NH.sub.2in which A is an aliphatic hydrocarbon radical having 6 to 30 C atoms, before, during or preferably after the coupling. The formulations are in particular suitable for intaglio printing inks which produce glossy prints which do not even strike through thin papers.
    Type: Grant
    Filed: February 5, 1982
    Date of Patent: May 7, 1985
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Peter Dopfer, Johann Ostermeier, Siegfried Schwerin