Nitrogen Bonded Directly At Alpha Position (i.e., 1-, 4-, 5- Or 8-position) Patents (Class 552/238)
  • Publication number: 20130225517
    Abstract: The invention provides compounds of formula I: or salts thereof as described herein. The invention also provides pharmaceutical compositions comprising a compound of formula I and therapeutic methods for treating cancer.
    Type: Application
    Filed: February 22, 2013
    Publication date: August 29, 2013
    Applicant: University of Iowa Research Foundation
    Inventor: University of Iowa Research Foundation
  • Patent number: 7901496
    Abstract: Disclosed is a phase change ink composition comprising a phase change ink carrier and a colorant compound of the formula wherein Y is a hydrogen atom or a bromine atom, n is an integer of 0, 1, 2, 3, or 4, R1 is an alkylene group, an arylene group, an arylalkylene group, or an alkylarylene group, provided that no oxygen atom creates a linkage, X is —O— or —NR3— wherein R3 is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, and R2 is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group.
    Type: Grant
    Filed: July 29, 2004
    Date of Patent: March 8, 2011
    Assignee: Xerox Corporation
    Inventors: Jeffrey H. Banning, Wolfgang G. Wedler, C. Wayne Jaeger
  • Patent number: 7683192
    Abstract: Disclosed is a colorant compound of the formula wherein Y is a hydrogen atom or a bromine atom, n is an integer of 0, 1, 2, 3, or 4, R1 is an alkylene group, an arylene group, an arylalkylene group, or an alkylarylene group, provided that no oxygen atom creates a linkage, X is —O— or —NR3— wherein R3 is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, and R2 is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group.
    Type: Grant
    Filed: July 29, 2004
    Date of Patent: March 23, 2010
    Assignee: Xerox Corporation
    Inventors: Jeffrey H. Banning, Wolfgang G. Wedler, C. Wayne Jaeger
  • Publication number: 20080201871
    Abstract: Quaternary ammonium salts were incorporated into anthraquinone dyes via a stable linkage. The structure of the antimicrobial colorants were characterized by Fourier Transform Infrared (FTIR), Nuclear Magnetic Resonance (NMR) and UV-vis spectrometry. The dyes demonstrated excellent antimicrobial ability against both gram-negative and gram-positive bacteria in aqueous solution, as indicated by very low minimum inhibitory concentration (MIC). The colorants showed excellent stability in water under light, continuous heating as well as acidic and alkaline conditions.
    Type: Application
    Filed: October 10, 2007
    Publication date: August 28, 2008
    Applicant: The Regents of the University of California
    Inventors: Gang Sun, Junshu Liu
  • Publication number: 20080168608
    Abstract: The subject of the present invention is the use, for dyeing in particular human keratin materials, of a specific direct anthraquinone dye by dry thermal transfer. Its subject is furthermore a method for dyeing keratin materials, in which at least one direct anthraquinone dye contained in a dry composition is applied to or close to the keratin materials, and a source of heat is applied, causing the thermal transfer of the direct dye(s) at the surface and/or inside the keratin materials. It relates furthermore to the dry composition and a method for preparing it.
    Type: Application
    Filed: February 28, 2006
    Publication date: July 17, 2008
    Inventors: Gregory Plos, Luc Gourlaouen, Jean-Dominique Bazin De Bezons
  • Publication number: 20080139830
    Abstract: Process for preparing substituted aminoanthraquinones by reacting 1,4-di-hydroxyanthraquinone with amines in the presence of dihydro-1,4-dihydroxyanthraquinone and a boric ester.
    Type: Application
    Filed: November 30, 2007
    Publication date: June 12, 2008
    Inventor: Horst Berneth
  • Patent number: 7244375
    Abstract: The present invention is related to a thermostable electroconductive polymer layer comprising an iodine-doped polymer layer based on 1-amino-9,10-anthraquinone having an electrical conductivity in the range of about 10?2 Sm/cm to about 102 Sm/cm. Additionally, the present invention is related to methods for preparing the thermostable electroconductive polymer layer. The method comprises polymerizing 1-amino-9,10-anthraquinone vapors at a reduced pressure in a direct current discharge on a cathode at a temperature in the range of about 150° C. to about 300° C., providing the necessary vapor pressure for a time period in the range of about 5 minutes to about 30 minutes and doping the prepared layer with iodine vapors.
    Type: Grant
    Filed: November 18, 2004
    Date of Patent: July 17, 2007
    Assignees: Samsung Electronics Co., Ltd., N S Enikolopov Institute of Synthetic Polymer Materials, Russian Academy of Sciences
    Inventors: Alexandr Ivanovich Drachev, Alla Borisovna Gilman, Alexandr Alexeevich Kuznetsov
  • Patent number: 7160335
    Abstract: The present invention relates to a compound of formula I wherein R1 and R3 are each independently of the other —NHR5, NHSO2R5, —NHCOR5, —OR6 or —SR7, R2 and R4 are each independently of the other —OR6 or —SR7, with the proviso that not all of the substituents R1 to R4 are —SR7, R5 is hydrogen, alkyl, aryl, aralkyl or a group of formula —(CnH2nX)m—H wherein X is —O—, —S—, —SO2—, —NH—, —NR8—, —CONH— or —CONR8— and R8 is alkyl or aryl, n is a number from 2 to 6 and m is a number from 1 to 10, R6 is aryl or heteroaryl and R7 is alkyl, aryl, heteroaryl or a group of formula —(CnH2nX)m—H wherein X is —O—, —S—, —SO2—, —NH—, —NR8—, CONH— or —CONR8— and R8 is alkyl or aryl, to a process for the preparation thereof and to the use thereof in a method of producing mass-coloured plastics or polymeric colour particles.
    Type: Grant
    Filed: March 13, 2003
    Date of Patent: January 9, 2007
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Urs Lauk, Patric Nowack, Alfons Arquint
  • Patent number: 7141685
    Abstract: Disclosed are thermally-stable, anthraquinone colorant compounds (dyes) which contain one or more vinyl groups which render the compounds copolymerizable with reactive vinyl monomers to produce colored, polymeric compositions such as acrylate and methacrylate polymeric materials. The compounds possess good fastness (stability) to ultraviolet (UV) light, good solubility in vinyl monomers, good color strength and excellent thermal stability. Also disclosed are (1) coating composition comprising (i) one or more polymerizable vinyl compounds, (ii) one or more of the dye compounds described above, and (iii) a photoinitiator and (2) polymeric materials, i.e., polymers derived from one or more acrylic acid esters, one or more methacrylic acid esters, one or more other polymerizable vinyl compounds or mixtures of any two or more thereof, having copolymerized therein one or more of the anthraquinone colorant compounds.
    Type: Grant
    Filed: December 12, 2003
    Date of Patent: November 28, 2006
    Assignee: Eastman Chemical Company
    Inventors: Michael John Cyr, Max Allen Weaver, Gerry Foust Rhodes, Jason Clay Pearson, Phillip Michael Cook, Jos Simon De Wit, Larry Keith Johnson
  • Patent number: 7052863
    Abstract: An alizarin-based chromogenic substrate, a composition containing the substrate, and its use to detect the presence of an enzymatic activity are disclosed. The substrate is particularly applicable in the field of biological diagnosis.
    Type: Grant
    Filed: December 11, 2000
    Date of Patent: May 30, 2006
    Assignee: Biomerieux S. A.
    Inventors: Lyle Armstrong, Arthur James
  • Patent number: 6740756
    Abstract: The present invention provides complexing agents of Formula I which contain novel photosensitizers and produce long-lived fluorescence for use in bioaffinity assays, especially HTRF (homogeneous time-resolved fluorescence) assays.
    Type: Grant
    Filed: June 20, 2001
    Date of Patent: May 25, 2004
    Assignee: SmithKline Beecham Corporation
    Inventors: George Wai-Kin Chan, Robert P. Hertzberg
  • Publication number: 20040087692
    Abstract: Disclosed herein is a method for producing a 1-[4-(biphenyl-4-carbonyl)]phenylaminoanthraquinone colorant composition where the method comprises: reacting 4-halobenzoic acid with about 1 mole to about 4 moles of a halogenating agent per mole of said 4-halobenzoic acid to form a 4-halobenzoyl halide composition; reacting in the presence of a first catalyst composition, said 4-halobenzoyl halide composition with biphenyl, in a solvent, to form a 1-[4-(biphenyl-4-carbonyl)]halobenzene composition; and reacting in the presence of a second catalyst composition and an acid scavenger, said 1-[4-(4-phenylbenzoyl)]halobenzene composition with a 1-aminoanthraquinone, in a reaction medium comprising a dipolar aprotic solvent, to form said 1-[4-(biphenyl-4-carbonyl)]phenylaminoanthraquinone colorant composition.
    Type: Application
    Filed: October 30, 2002
    Publication date: May 6, 2004
    Inventors: Arun Nandkishor Dixit, Adil Minoo Dhalla
  • Patent number: 6727372
    Abstract: Disclosed are novel colorant compounds which contain one or more ethylenically-unsaturated (vinyl), photopolymerizable radicals which may be copolymewrized (or cured) with ethylenically-unsaturated monomers to produce colored compositions such as colored acrylic coatings and polymers, e.g., coatings and polymers produced from acrylate and methacrylate esters, colored polystyrenes, and similar colored polymeric materials derived from other ethylenically-unsaturated monomers. The present invention also pertains to processes for the preparation of certain of the photopolymerizable colorant compounds.
    Type: Grant
    Filed: August 2, 2001
    Date of Patent: April 27, 2004
    Assignee: Eastman Chemical Company
    Inventors: Michael John Cyr, Max Allen Weaver, Gerry Foust Rhodes, Jason Clay Pearson, Phillip Michael Cook
  • Patent number: 6713641
    Abstract: Disclosed are blue, diol anthraquinone blue colorant compounds having excellent thermal stability and which can be reacted into or copolymerized with polyester thus providing a blue-colored polyesters useful for manufacturing a variety of shaped articles such as photographic film base, particularly roentgenographic (X-ray) film. Also disclosed are blue anthraquinone colorant compounds which contain two ethylenically-unsaturated (vinyl), photopolymerizable radicals which may be derived from the aforesaid diol anthraquinone compounds. The anthraquinone colorant compounds containing two ethylenically-unsaturated may be reacted into or copolymerized (or cured) with ethylenically-unsaturated monomers to produce colored vinyl polymers.
    Type: Grant
    Filed: October 19, 2001
    Date of Patent: March 30, 2004
    Assignee: Eastman Chemical Company
    Inventors: Max Allen Weaver, Gerry Foust Rhodes, Jason Clay Pearson, Sara Stanley Wells, Michael John Cyr
  • Patent number: 6635350
    Abstract: Red colorants comprising a chromophore having at least one poly(oxyalkylene) chain attached to the 1-position, as well as at least one poly(oxyalkylene) chain attached to either the 5-position or the 8-position of an anthraquinone backbone are provided. Such colorants exhibit excellent base stability, effective colorations, excellent low extraction rates, and high lightfastness levels, particularly when incorporated within certain media and/or on the surface of certain substrates, particularly polyesters. The poly(oxyalkylene) chains also increase the solubility in different solvents or resins thereby permitting the introduction of such excellent coloring chromophores within diverse media and/or diverse substrates as well as provides a liquid colorant which facilitates handling. Compositions and articles comprising such colorants are provided as well as methods for producing such inventive colorants are also provided.
    Type: Grant
    Filed: October 16, 2001
    Date of Patent: October 21, 2003
    Assignee: Milliken & Company
    Inventors: Daniel M. Connor, John W. Miley, Jr.
  • Patent number: 6596884
    Abstract: A method for synthesizing hydrogen peroxide comprises the steps of: synthesizing an analog of anthraquinone that is miscible or soluble in carbon dioxide; reacting the analog of anthraquinone with hydrogen in carbon dioxide to produce a corresponding analog of tetrahydroquinone; and reacting the analog of tetrahydroquinone with oxygen to produce the hydrogen peroxide and regenerate the analog of anthraquinone. A chemical compound having the formula: wherein R1, R2, R3, R4, R5, R6, R7, and R8 are independently, the same or different, H, RC, or RSRC, wherein RS is a spacer group and RC is a fluoroalkyl group, a fluoroether group, a silicone group, an alkylene oxide group, a fluorinated acrylate group, or a phosphazine group, and wherein at least one of R1, R2, R3, R4, R5, R6, R7, and R8 is not H.
    Type: Grant
    Filed: November 30, 2001
    Date of Patent: July 22, 2003
    Assignee: University of Pittsburgh
    Inventors: Eric J. Beckman, Dan Hâncu
  • Publication number: 20030082667
    Abstract: The invention concerns a novel chromogenic substrate based on Alizarin. The invention also concerns the uses to which this substrate can be put, and a formulation containing such a substrate.
    Type: Application
    Filed: June 3, 2002
    Publication date: May 1, 2003
    Inventors: Lyle Armstrong, Arthur James
  • Publication number: 20030073853
    Abstract: Cationic aminoanthraquinones in which at least one cationic charge is delocalized on a 5-membered unsaturated polynitrogen-containing heterocycle, their use as a direct dye in dyeing compositions for keratinous materials, in particular for human keratinous fibers such as hair, dyeing compositions containing them, and dyeing methods using these compositions.
    Type: Application
    Filed: July 9, 2002
    Publication date: April 17, 2003
    Applicant: L'Oreal S.A.
    Inventors: Alain Genet, Alain Lagrange
  • Patent number: 6485559
    Abstract: The present Application relates to pigment colourants of formula wherein R1 is C1-C6alkyl, C1-C6alkoxy, phenoxy or halogen, R2 is hydrogen, C1-C6alkyl, C1-C6alkoxy, phenoxy, halogen, acylamino, —CH2NHacyl or the radical and R3 is C1-C6alkyl, C1-C6alkoxy, phenoxy or halogen, the ring A may be further substituted by —SO3−M+, wherein M+ is a cation, and the rings B and C may be unsubstituted or further mono- or poly-substituted by halogen, hydroxy, —SH, amino, C1-C6alkylamino, C1-C6alkyl, C1-C6alkoxy, phenoxy, acylamino, C1-C6thioalkyl or by thiophenyl, and the ring B may be substituted in the 5- or 8-position by a radical of formula wherein R1, R2 and R3 are as defined above, to a process for their preparation, and to their use in the mass-coloring of synthetic materials.
    Type: Grant
    Filed: December 27, 2000
    Date of Patent: November 26, 2002
    Assignee: Ciba Specialty Chemicals Corporation
    Inventor: Jean-Marie Adam
  • Patent number: 6437155
    Abstract: Solid inks and toners contain at least one colorant that includes at least one substituted-9,10-anthraquinone compound, substituted with at least one monofunctional amine. The colorant can be formed very efficiently, and the product can be used in desirable image formation methods.
    Type: Grant
    Filed: August 24, 2001
    Date of Patent: August 20, 2002
    Assignee: Xerox Corporation
    Inventors: Donald R. Titterington, Jeffery H. Banning
  • Patent number: 6420576
    Abstract: The process for preparing arylaminohydroxyanthraquinone of the formula by reacting appropriate chlorohydroxyanthraquinone with an amine of the formula (III) H2N—Ar  (III), is characterized in that one mole of amine of the formula (III) plus an excess of 10 to 100% based on one mole of amine is used per chlorine atom in the compounds of the formula (II) and the reaction is carried out in an inert solvent in the presence of a base selected from the group consisting of the carbonates of the alkali and alkaline earth metals, the acetates of the alkali metals, the phosphates of the alkali metals and any mixtures thereof.
    Type: Grant
    Filed: July 26, 2000
    Date of Patent: July 16, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Josef-Walter Stawitz, Stephan Michaelis
  • Publication number: 20020043178
    Abstract: The present invention provides a method for reducing dust deposits on polyolefin films. Further subjects of the invention are the use of a polyetheresteramide for reducing dust deposits on polyolefin films and coextruded multilayer polyolefin films containing a polyetheresteramide at least in one outer layer.
    Type: Application
    Filed: August 27, 2001
    Publication date: April 18, 2002
    Inventors: Nicola Lelli, Nadi Ergenc
  • Publication number: 20020016480
    Abstract: Solid inks and toners contain at least one colorant that includes at least one substituted-9,10-anthraquinone compound, substituted with at least one monofunctional amine. The colorant can be formed very efficiently, and the product can be used in desirable image formation methods.
    Type: Application
    Filed: August 24, 2001
    Publication date: February 7, 2002
    Applicant: Xerox Corporation
    Inventors: Donald R. Titterington, Jeffery H. Banning
  • Patent number: 6090165
    Abstract: Dye mixtures which contain a dye of the formula ##STR1## together with a dye of the formula ##STR2## in which M.sup.+ in the dyes of the formulae (1) and (2) are ammonium cations ##STR3## which are identical to or different from one another, of an amine of the formula ##STR4## where R.sub.1 and R.sub.2 independently of one another are hydrogen, C.sub.1 --C.sub.6 alkyl or C.sub.2 --C.sub.6 alkyl substituted by hydroxyl or amino and, if appropriate, interrupted by an oxygen atom, and R.sub.3 is C.sub.2 --C.sub.6 alkyl substituted by hydroxyl or amino and, if appropriate, interrupted by an oxygen atom, afford dyeings having good fastnesses on nitrogen-containing or hydroxyl group-containing fibre materials.
    Type: Grant
    Filed: February 10, 1998
    Date of Patent: July 18, 2000
    Assignee: Ciba Specialty Chemicals Corporation
    Inventor: Roger Lacroix
  • Patent number: 6051360
    Abstract: Dyestuffs represented by the below-described formula (1), that is, dyestuffs formed of a chromophoric nucleus and a bisphenol introduced therein have excellent solubility in solvents and binder resins, and can provide color filters having excellent transmittance characteristics and durability. ##STR1## wherein Dye represents a chromophoric nucleus, X represents a direct bond or a divalent connecting group, R.sup.1 to R.sup.10 and n are defined with the provision that one of R.sup.9 and R.sup.10 has 3 or more carbon atoms.
    Type: Grant
    Filed: December 31, 1997
    Date of Patent: April 18, 2000
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Akio Karasawa, Hisato Itoh
  • Patent number: 6033445
    Abstract: Concentrated aqueous dye solutions, which comprise 5 to 50% by weight of at least one dye of formula (1) ##STR1## wherein X and Y are each independently of the other hydrogen or C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, and Z is C.sub.2 -C.sub.6 alkanoylamino or C.sub.2 -C.sub.4 hydroxyalkylsulfamoyl,M.sup.+ is the ammonium cation ##STR2## of an amine of formula ##STR3## wherein R.sub.1 and R.sub.2 are each independently of the other hydrogen, C.sub.1 -C.sub.6 alkyl, or hydroxy- or amino-substituted C.sub.2 -C.sub.6 alkyl which may be interrupted by an oxygen atom, and R.sub.3 is hydroxy- or amino-substituted C.sub.2 -C.sub.6 alkyl which may be interrupted by an oxygen atom, with the proviso that R.sub.1, R.sub.2 and R.sub.3 are not a radical of formula --CH.sub.2 --CH(OH)--CH.sub.
    Type: Grant
    Filed: December 9, 1998
    Date of Patent: March 7, 2000
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Roger Lacroix, Jean-Marie Adam
  • Patent number: 5733880
    Abstract: A compound having the structural formula, ##STR1## where R.sup.1 and R.sup.2 are independently hydrogen or hydroxyl. R.sup.2 and R.sup.3 are independently oxo or hydrogen, one of R.sup.5 and R.sup.6 is A--B and the other is hydrogen, hydroxyl, or a group A, wherein each A is a spacer group providing --NH-- or --CO-- in the bond with B (if present); at least one A group does not provide the residue of an .alpha.-amino acid adjacent the anthraquinone nucleus and the A of any A--B moiety is joined to the anthraquinone nucleus via an --NH-- bond, and each B is a peptide group or a physiologically acceptable derivative thereof. The compounds are useful as antitumor compounds.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: March 31, 1998
    Assignee: Napier University Ventures Limited
    Inventor: David John Mincher
  • Patent number: 5679808
    Abstract: The present invention discloses a tertiary non-linear optical material comprising a quinone derivative expressed by any one of the general formulas: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are as defined above, or the formula: ##STR2## The tertiary non-linear material enables the co-existence of large tertiary non-linear optical susceptibility and high-speed response.
    Type: Grant
    Filed: January 26, 1995
    Date of Patent: October 21, 1997
    Assignee: Sumitomo Electric Industries, Ltd.
    Inventors: Akira Mizoguchi, Yasuhiro Hattori, Michiru Kubata
  • Patent number: 5639896
    Abstract: A process for the preparation of N,N'-disubstituted 1,4-diaminoanthraquinones has been found which is characterized in that 1,4-dihydroxyanthraquinones are reacted with aliphatic or aromatic amines in the presence of a hydroxycarboxylic acid as a condensation auxiliary.
    Type: Grant
    Filed: May 3, 1996
    Date of Patent: June 17, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dietmar Kalz, Reinold Schmitz, Karl-Heinz Reinhardt, Josef Schroder, Stephan Michaelis
  • Patent number: 5504199
    Abstract: A dye which is either 2-naphthalenol (phenylazo) phenyl azo alkyl derivatives and 1,4-dialkylamino anthraquinone is added to sufficient non-ionic surfactant to compatibilize it with ethanol and an solvent to produce a homogeneous solution. The homogeneous solution is added to ethanol in an amount to provide a desired amount of coloration to the ethanol.
    Type: Grant
    Filed: October 28, 1994
    Date of Patent: April 2, 1996
    Assignee: Morton International, Inc.
    Inventors: Alejandra Zimin, Peter A. Caputo, Michael R. Friswell, David L. Booth, Michael P. Hinton
  • Patent number: 5387704
    Abstract: Process for preparing amino- and carbamoyl-substituted anthraquinones by Diels-Alder reaction of an N-butadienylcarbamic acid ester of the formula H.sub.2 C.dbd.CH--CH.dbd.CH--NH--COOR.sup.2, wherein R.sup.2 is alkyl or phenylalkyl, with a 1,4-naphthoquinone or with 1,4-benzoquinone to form a carbamoyl-substituted hydroanthraquinone intermediate and by oxidation of this intermediate with an oxygen-containing gas in a tertiary amine and in the presence of a copper salt to obtain a carbamoyl-substituted anthraquinone product. The Diels-Alder reaction and the oxidation reaction can be carried out as a one-pot synthesis or in separate steps. The carbamic acid ester reactant provides a blocking group represented by --COOR.sup.2, and this blocking group is optionally removed by treatment of the carbamoyl-substituted anthraquinone with an alkaline hydroxide solution.
    Type: Grant
    Filed: November 9, 1993
    Date of Patent: February 7, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Ebel, Juergen Schroeder
  • Patent number: 5237077
    Abstract: The present invention relates to a process for producing an aromatic nitro compound by introducing a nitrogen oxide gas and ozone-containing oxygen or air into a halogenated organic solvent dissolving or suspending therein an aromatic compound, thereby subjecting the aromatic compound to nitration. By the use of a system comprising the nitrogen oxide and ozone-containing oxygen or air as the nitrating agent, the aromatic nitro compound can be produced under mild conditions without using any mineral acid. In addition, the various disadvantages due to the use of mineral acid in the conventional process can be avoided by the process of the present invention.
    Type: Grant
    Filed: March 27, 1992
    Date of Patent: August 17, 1993
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Hitomi Suzuki, Takashi Murashima, Kenkichi Tsukamoto
  • Patent number: 5213665
    Abstract: A process for producing 1-aminoanthraquinones represented by formula (C) ##STR1## wherein R.sup.1 and R.sup.2, independently from each other, denote one type selected from a hydrogen atom, an alkyl group having 1 to 4 carbon atoms and a halogen atom,which comprises converting 5-nitro-1,4,4a,9a-tetrahydroanthraquinones represented by formula (A) ##STR2## wherein R.sup.1 and R.sup.2 are as defined above, into 1-hydroxylaminoanthraquinones represented by formula (B) ##STR3## wherein R.sup.1 and R.sup.2 are as defined above, in the presence of a basic compound, and electrolytically reducing the resulting 1-hydroxylaminoanthraquinones in the presence of a basic compound.
    Type: Grant
    Filed: April 8, 1991
    Date of Patent: May 25, 1993
    Assignee: Nippon Shokubai Kagaku Kogyo, Co., Ltd.
    Inventors: Noboru Sugishima, Noriaki Ikeda, Yasushi Fujii, Akira Inoue
  • Patent number: 5149848
    Abstract: A process for producing 1-aminoanthraquinones represented by the formula (C) ##STR1## wherein R.sup.1 and R.sup.2, independently from each other, denote one type selected from a hydrogen atom, an alkyl group having 1 to 4 carbon atoms and a halogen atom,which comprises converting 5-nitro-1,4,4a,9a-tetrahydroanthraquinones respresented by formula (A) ##STR2## wherein R.sup.1 and R.sup.2 are as defined above, into 1-hydroxylaminoanthraquinones represented by formula (B) ##STR3## wherein R.sup.1 and R.sup.2 are as defined above, in the presence of a basic compound, and electrolytically reducing the resulting 1-hydroxylaminoanthraquinones in the presence of a basic compound.
    Type: Grant
    Filed: April 8, 1991
    Date of Patent: September 22, 1992
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Noboru Sugishima, Noriaki Ikeda, Yasushi Fujii, Akira Inoue
  • Patent number: 5141957
    Abstract: The present invention provides novel substituted anthraquinones having the formula ##STR1## wherein R.sub.1 and R.sub.2 are independently H, alkyl, aryl, or arylalkyl;m and n are independently 1, 2, or 3;X is H, OH, NR.sub.3 R.sub.4, Cl, Br, I, F, alkyl, aryl alkoxy, aroxy, COOR.sub.5, or CONR.sub.6 R.sub.7 ;R.sub.3, R.sub.4, R.sub.5, R.sub.6, and R.sub.7 are independently H, lower alkyl or aryluseful for inhibiting protein kinase C and treating conditions related to, or affected by inhibition of protein kinase C, particularly cancer tumors, inflammatory disease, reperfusion injury, and cardiac dysfunctions related to reperfusion injury.
    Type: Grant
    Filed: November 5, 1990
    Date of Patent: August 25, 1992
    Assignee: Sphinx Pharmaceuticals Corporation
    Inventors: Jack B. Jiang, Mary G. Johnson
  • Patent number: 5132327
    Abstract: Compounds of formula (I) ##STR1## in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each separately selected from hydrogen, X, NH--A--NHR and NH--A--N(O)R'R" wherein X is hydroxy, halogeno, amino, C.sub.1-4 alkoxy or C.sub.2-8 alkanoyloxy, A is a C.sub.2-4 alkylene group with a chain length between NH and NHR or N(O)R'R" of at least 2 carbon atoms and R, R' and R" are each separately selected from C.sub.1-4 alkyl groups and C.sub.2-4 hydroxyalkyl and C.sub.2-4 dihydroxyalkyl groups in which the carbon atom attached to the nitrogen atom does not carry a hydroxy group and no carbon atom is substituted by two hydroxy groups, or R' and R" together are a C.sub.2-6 alkylene group which with the nitrogen atom to which R" and R" are attached forms a heterocyclic group having 3 to 7 atoms in the ring, but with the proviso that at least one of R.sub.1 to R.sub.4 is a group NH--A--N(O)R'R", and physiologically acceptable salts thereof are of value in the treatment of cancer.
    Type: Grant
    Filed: April 10, 1991
    Date of Patent: July 21, 1992
    Assignee: National Research Development Corporation
    Inventor: Laurence H. Patterson
  • Patent number: 5132437
    Abstract: 1-Aminoanthraquinone (1-AAQ) is synthesized by the reaction of 2-chlorobenzyl chloride and xylene in the presence of a solid acid catalyst to yield 2-chloro dimethyldiphenylmethane, subsequent oxidation of the methyl groups, ring closure to form a 1-chloroanthraquinone carboxylic acid, replacement of the 1-chloro group with ammonia, and decarboxylation.
    Type: Grant
    Filed: February 12, 1991
    Date of Patent: July 21, 1992
    Assignee: Hoechst Celanese Corporation
    Inventors: Mohammad Aslam, Daniel A. Aguilar
  • Patent number: 5112997
    Abstract: Aminoanthraquinones which are materials for dyes are prepared by allowing nitroanthraquinones to react with carbon monoxide and water in a liquid phase in the presence of a homogeneous catalyst comprising rhodium compounds or ruthenium compounds and solvents therefor.
    Type: Grant
    Filed: October 29, 1990
    Date of Patent: May 12, 1992
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Kotohiro Nomura, Masaru Ishino
  • Patent number: 5087755
    Abstract: A process for producing an aromatic amine under moderate conditions is provided wherein a catalyst higher in activity than conventional catalysts is used. Reduction of an aromatic nitro compound under a CO/H.sub.2 O system is conducted using a rhodium compound catalyst in the presence of an aqueous alkali solution such as aqueous sodium hydroxide solution. Alternatively, an aromatic nitro compound is reduced under a CO/H.sub.2 O system using a rhodium compound or a ruthenium compound catalyst in the presence of the aqueous alkali solution and additionally at least one compound of amine compounds, diamine compounds, phosphine compounds, phosphite compounds, and diphosphine compounds.
    Type: Grant
    Filed: November 15, 1989
    Date of Patent: February 11, 1992
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kotohiro Nomura, Masaru Ishino
  • Patent number: 5055602
    Abstract: Dye monomers of the general chemical formula ##STR1## where X denotes an unsaturated polymerizable organic radical; andR is an organic diradical with 2 to 12 carbon atoms.
    Type: Grant
    Filed: April 3, 1990
    Date of Patent: October 8, 1991
    Assignee: Bausch & Lomb Incorporated
    Inventor: John B. Melpolder
  • Patent number: 5032670
    Abstract: Disclosed are color concentrate compositions which comprise a polyester having copolymerized therein at least 0.5 weight percent of an anthraquinone colorant compound having the formula ##STR1## wherein AQ is a 1,5- or 1,8-anthraquinonylene radical; R.sup.1 and R.sup.2 are the same or different and are unsubstituted or substituted alkyl, cycloalkyl or aryl; and X is a group reactive with at least one of the functional groups of the monomers from which the polyester is prepared. Amorphous polyesters and partially-crystalline polyesters are preferred embodiments of the color concentrates. Also disclosed are colored semicrystalline powders which may be obtained from the amorphous and partially-crystalline color concentrates by a dissolution-crystallization-precipitation procedure.
    Type: Grant
    Filed: August 30, 1989
    Date of Patent: July 16, 1991
    Assignee: Eastman Kodak Company
    Inventors: William W. Parham, James J. Krutak, Max A. Weaver, Clarence A. Coates, Jr., Terry A. Oldfield
  • Patent number: 5030387
    Abstract: An organic conductive complex comprising an electron donor and an electron acceptor, the electron donor being an anthraquinone derivative represented by formula (1): ##STR1## wherein X.sup.1, X.sup.2, X.sup.3 and X.sup.4, which may be the same or different, each represents an electron donating group.
    Type: Grant
    Filed: June 27, 1989
    Date of Patent: July 9, 1991
    Assignee: Sumitomo Electric Industries Ltd.
    Inventors: Masaru Matsuoka, Teijiro Kitao, Yo Shimizu
  • Patent number: 4977281
    Abstract: Primary amino polyoxyalkylene 1,3-dioxane or 1,3-dioxolane compounds are provided of the formula: ##STR1## wherein R and R.sub.1 are independently selected from hydrogen or a lower alkyl group; R.sub.2 and R.sub.3 are independently selected from hydrogen, phenyl or lower alkyl groups; R.sub.4 is selected from hydrogen or a lower alkyl group; x is 0 or 1; N and M are each integers of from 1 to about 100 and the sum of N an M is from 2 to about 100; also disclosed are polyoxyalkylene amino alcohol compounds which may be derived from the compounds of Formula I above having the formula: ##STR2## wherein R, R.sub.1, R.sub.4, x, N and M all have the values given above. Also provided is a process for preparing a primary amino polyoxyalkylene 1,3-dioxane or 1,3-dioxolane.
    Type: Grant
    Filed: December 21, 1987
    Date of Patent: December 11, 1990
    Assignee: Milliken Research Corporation
    Inventors: John W. Miley, John W. Rekers
  • Patent number: 4940692
    Abstract: Heat transferable dyes which compared with the prior art show better solubility and/or higher light fastness and good to excellent transfer properties have the formula (I) ##STR1## where X is H or CN, R.sup.1, R.sup.2, and R.sup.3 independently of one another are alkyl, alkylcarbonyloxyalkyl, alkoxycarbonyloxyalkyl, alkoxycarbonylalkyl, haloalkyl, hydroxyalkyl, cyanoalkyl, unsubstituted or alkyl-or alkoxy-substituted phenyl or benzyl or a radical of the formula--Y--O].sub.m R.sup.4 (II)where Y is C.sub.2 -C.sub.6 -alkylene, m is 1 to 6 and R.sup.4 is alkyl or phenyl, with the proviso that if X is H then R.sup.1 and R.sup.3 are each substituted or unsubstituted alkyl or substituted or unsubstituted phenyl or if X is H and R.sup.1 is H, then R.sup.3 must be substituted or unsubstituted phenyl.
    Type: Grant
    Filed: April 3, 1989
    Date of Patent: July 10, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Volker Bach, Ruediger Sens, Karl-Heinz Etzbach, Manfred Ruske