Plural Monocyclic Benzene Rings, Each Bonded Directly To An Azo Group, Are Between The Azo Groups Patents (Class 534/759)
  • Patent number: 8992633
    Abstract: Disclosed are compounds of formula (1) or formula (2). The compounds are useful for the dyeing of organic materials, such as keratin fibers, wool, leather, silk, cellulose or polyamides, especially keratin-containing fibers, cotton or nylon, and preferably hair, more preferably human hair. (1) (2).
    Type: Grant
    Filed: May 2, 2012
    Date of Patent: March 31, 2015
    Assignee: BASF SE
    Inventors: Sophie Marquais-Bienewald, Christian Cremer, Beate Frohling
  • Patent number: 8541557
    Abstract: An azo compound having the following formula (I): A(E)n??(I) wherein A represents a residue of an azo compound, bonded with n pieces of E group through one or more heteroatom being N or O and forming a part of the residue A; E independently represents a hydrogen atom or —C(?O)—O—R1 wherein R1 represents a substituted or an unsubstituted alkyl group having 4 to 10 carbon atoms, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group or an aralkyl group; and n represents an integer of from 1 to 10.
    Type: Grant
    Filed: June 15, 2012
    Date of Patent: September 24, 2013
    Assignee: Ricoh Company, Ltd.
    Inventor: Masafumi Ohta
  • Patent number: 8357673
    Abstract: A series of mono- and binuclear 4-arylazo-3,5-diamino-pyrazoles which are useful for inhibition of cyclin-dependent kinases (preferably CDK9). Hence they can be used as antimitotic-, pro-apoptotic and antiinflammatory drugs, in particular, in chemotherapy of cancer and asthma, therapy of psoriasis and parasitoses as those caused by fungi or protists, treatment of Alzheimer's disease or as antineurodegenerative drugs, or to suppress immunostimulation. These compounds are useful in a variety of utilities, including as intermediates in the preparation of flame-retardants, diagnostic reagents and therapeutics, including antivirals and immunosuppressors.
    Type: Grant
    Filed: September 1, 2005
    Date of Patent: January 22, 2013
    Assignee: Univerzita Palackeho V Olomouci
    Inventors: Petr Cankar, Iveta Frysova, Vladimir Krystof, Rene Lenobel, Jan Slouka, Miroslav Strnad, Peter Martin Fischer
  • Patent number: 8309696
    Abstract: The present invention provides an azo pigment comprising a group represented by the general formula (1) below, an electrophotographic photosensitive member comprising an intermediate layer comprising the azo pigment, and a process cartridge and an electrophotographic apparatus that comprise the electrophotographic photosensitive member.
    Type: Grant
    Filed: August 31, 2009
    Date of Patent: November 13, 2012
    Assignee: Canon Kabushiki Kaisha
    Inventors: Atsushi Fujii, Mai Murakami
  • Publication number: 20120253025
    Abstract: An azo compound having the following formula (I): A(E)n??(I) wherein A represents a residue of an azo compound, bonded with n pieces of E group through one or more heteroatom being N or O and forming a part of the residue A; E independently represents a hydrogen atom or —C(?O)—O—R1 wherein R1 represents a substituted or an unsubstituted alkyl group having 4 to 10 carbon atoms, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group or an aralkyl group; and n represents an integer of from 1 to 10.
    Type: Application
    Filed: June 15, 2012
    Publication date: October 4, 2012
    Applicant: RICOH COMPANY, LTD.
    Inventor: Masafumi OHTA
  • Patent number: 8101731
    Abstract: The present invention relates to novel yellow anionic dyes, a process for their preparation, certain novel intermediates necessary for their preparation and the use of these dyes for dyeing natural or synthetic materials, in particular, paper. The dyes are of formula (14), (15) or (16) in which R1 represents hydrogen, C1-C4alkyl, C1-C4alkoxy or SO3H, R2 represents SO3H or CO2H, R3 represents hydrogen, C1-C4alkyl, halogen, hydroxy, C1-C4alkoxy, carboxy, NH2 or NHC1-C4alkyl, R3a represents hydrogen or NH2 and A1 and A2, independently of the other, is selected from the group consisting of an acetoacetylated amine, a derivative of barbituric acid, a 2,4,6-triaminopyrimidine derivative, a pyridone derivative, an aminopyrazole or a pyrazolone derivative and a benzoic acid derivative, or A1 and A2, each one independently of the other, represent a certain phenol residue.
    Type: Grant
    Filed: March 29, 2010
    Date of Patent: January 24, 2012
    Inventors: Michael Lennartz, Adolf Käser, Sandra Weiss
  • Publication number: 20100199443
    Abstract: The present invention relates to novel yellow anionic dyes, a process for their preparation, certain novel intermediates necessary for their preparation and the use of these dyes for dyeing natural or synthetic materials, in particular, paper. The dyes are of formula (14), (15) or (16) in which R1 represents hydrogen, C1-C4alkyl, C1-C4alkoxy or SO3H, R2 represents SO3H or CO2H, R3 represents hydrogen, C1-C4alkyl, halogen, hydroxy, C1-C4alkoxy, carboxy, NH2 or NHC1-C4alkyl, R3a represents hydrogen or NH2 and A1 and A2, independently of the other, is selected from the group consisting of an acetoacetylated amine, a derivative of barbituric acid, a 2,4,6-triaminopyrimidine derivative, a pyridone derivative, an aminopyrazole or a pyrazolone derivative and a benzoic acid derivative, or A1 and A2, each one independently of the other, represent a certain phenol residue.
    Type: Application
    Filed: March 29, 2010
    Publication date: August 12, 2010
    Inventors: Michael Lennartz, Adolf Kåser, Sandra Weiss
  • Patent number: 7772377
    Abstract: Disclosed is a colorant composition of the formula wherein R is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, and wherein R can be joined to the phenyl moiety to form a ring, R? is an aromatic- or heteroaromatic-containing group, each Ra, independently of the others, is a halogen atom, an alkyl group, an alkoxy group, a nitrile group, a nitro group, an amide group, or a sulfonamide group, w is an integer of 0, 1, 2, 3, or 4, n is an integer representing the number of carbon atoms in each repeat alkylene oxide unit, and x is an integer representing the number of repeat alkylene oxide units, wherein said colorant has no more than one —OH, —SH, or primary or secondary amino group per molecule.
    Type: Grant
    Filed: January 25, 2008
    Date of Patent: August 10, 2010
    Assignee: Xerox Corporation
    Inventors: Jeffrey H Banning, Donald R Titterington, Clifford R King
  • Patent number: 7732581
    Abstract: Disclosed is a compound of the formula and dimers thereof, wherein R, R?, X, (Y)m, and (Z)n are as defined herein. The compounds are useful as colorants, particularly in applications such as phase change inks.
    Type: Grant
    Filed: March 25, 2009
    Date of Patent: June 8, 2010
    Assignee: Xerox Corporation
    Inventors: Jeffrey H. Banning, James D. Mayo, Rina Carlini
  • Patent number: 7723494
    Abstract: The present invention relates to novel yellow anionic dyes, a process for their preparation, certain novel intermediates necessary for their preparation and the use of these dyes for dyeing natural or synthetic materials, in particular, paper.
    Type: Grant
    Filed: January 4, 2008
    Date of Patent: May 25, 2010
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Michael Lennartz, Adolf Käser, Sandra Weiss
  • Patent number: 7619075
    Abstract: Disclosed is a colorant composition of the formula wherein R is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, and wherein R can be joined to the phenyl moiety to form a ring, R? is an aromatic- or heteroaromatic-containing group, each Ra, independently of the others, is a halogen atom, an alkyl group, an alkoxy group, a nitrile group, a nitro group, an amide group, or a sulfonamide group, w is an integer of 0, 1, 2, 3, or 4, n is an integer representing the number of carbon atoms in each repeat alkylene oxide unit, and x is an integer representing the number of repeat alkylene oxide units, wherein said colorant has no more than one —OH, —SH, or primary or secondary amino group per molecule.
    Type: Grant
    Filed: August 16, 2005
    Date of Patent: November 17, 2009
    Assignee: Xerox Corporation
    Inventors: Jeffery H. Banning, Donald R. Titterington, Clifford R. King
  • Patent number: 7488354
    Abstract: Disclosed herein is a dyeing composition comprising a particular disulphide dye and a method of dyeing human keratin fibers, such as hair, using this composition. This composition makes it possible to obtain particularly fast chromatic colorations.
    Type: Grant
    Filed: October 14, 2005
    Date of Patent: February 10, 2009
    Assignee: L'Oreal S.A.
    Inventors: Nicolas Daubress, Gilles Genain
  • Patent number: 7476260
    Abstract: Formula (I) wherein R1 and R2 each independently from each other are a residue of an organic dye: Y1 and Y2 each independently from each other are unsubstituted or substituted, straightchain or branched, interrupted or uninterrupted —C1-C10alkylene-; —C5-C10cycloalkylene-; C5-C10arylene; or —C5-C10arylene-(C1-C10alkylene)-; Z1 and Z2 independently from each other are Formula (II) are each independently from each other hydrogen; or unsubstituted or substituted, straight-chain or branched, mono-cyclic or polycyclic, interrupted or uninterrupted C1-C14alkyl; C2-C14alkenyl; C6-C10aryl; C6-C10aryl-C1-C10alkyl; or C5-C10alkyl(C5-C10aryl); r, q and n independently from each other are 0 or 1, if n is 0, Z3 is hydrogen; and if n is 1, Z3 is —S—: with the proviso that the method does not comprise treating the fiber with an enzyme of the type of a protein disulfidisomerase (EC 5.3.4.1).
    Type: Grant
    Filed: March 29, 2005
    Date of Patent: January 13, 2009
    Assignee: Ciba Specialty Chemicals Corp.
    Inventors: Victor Paul Eliu, Beate Fröhling, Dominique Kauffmann
  • Patent number: 6923855
    Abstract: An ink, which contains at least one dye of formula (1): A—N?N—BX1n1B?—N?N—A???Formula (1) wherein A and A? each independently represent an aryl group or a monovalent heterocyclic group; B and B? each independently represent an arylene group or a divalent heterocyclic group; X1 represents a divalent linking group; n1 is 0 or 1; and at least one of A, B, A?, and B? is a heterocyclic group.
    Type: Grant
    Filed: August 1, 2003
    Date of Patent: August 2, 2005
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toru Harada, Naotaka Wachi
  • Patent number: 6713614
    Abstract: Disclosed are compounds of the formula The compounds are useful as colorants, particularly in applications such as phase change inks.
    Type: Grant
    Filed: June 27, 2002
    Date of Patent: March 30, 2004
    Assignee: Xerox Corporation
    Inventors: Rina Carlini, Jeffrey H. Banning, James M. Duff, Bo Wu, James D. Mayo
  • Patent number: 6576748
    Abstract: Disclosed is a process for preparing a diazopyridone compound either (A) of the formula or (B) of the formula which comprises diazotizing a dianiline and coupling it with a pyridone or diazotizing an aniline and coupling it with a dipyridone.
    Type: Grant
    Filed: June 27, 2002
    Date of Patent: June 10, 2003
    Assignee: Xerox Corporation
    Inventors: Rina Carlini, James D. Mayo, James M. Duff, Jeffrey H. Banning, Paul F. Smith, George Liebermann, Roger E. Gaynor
  • Patent number: 6140478
    Abstract: Basic azo compounds of formula I are suitable for coloring or printing especially of paper and leather.
    Type: Grant
    Filed: July 19, 1996
    Date of Patent: October 31, 2000
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Jurgen Geiwiz, Helmut Anton Moser, Reinhard Pedrazzi
  • Patent number: 5693766
    Abstract: A thermal transfer sheet comprising a substrate having a coating comprising a dye of Formula (1): ##STR1## wherein: Y is --H, alkyl, alkoxy, --NHCOalkyl, NHCOaryl, --NHSO.sub.2 alkyl or --NHSO.sub.2 aryl;Ring A is unsubstituted apart from the --N.dbd.N--, --Y and --N< groups or may be substituted by from 1 to 3 substituent groups;R.sup.1 and R.sup.2 each independently is alkyl;R.sup.3 is --H, alkyl, aryl, --SO.sub.2 alkyl, --Salkyl, --Saryl, halogen, pyridyl or R.sup.6 O(CH.sub.2).sub.n -- in which R.sup.6 is alkyl, acyl, aryl and n is from 1 to 10;R.sup.4 is --CN, --NO.sub.2, --SCN or --COOalkyl; andR.sup.5 is a group of Formula (2): ##STR2## in which: Z is --H, alkyl, alkoxy, --NHCOalkyl, --NHCOaryl, --NHSO.sub.2 alkyl or --NHSO.sub.2 aryl;Ring B is unsubstituted apart from the --N.dbd.N--, --Z and --N< groups or may be substituted by from 1 to 3 substituent groups;R.sup.7 and R.sup.8 each independently is --H or alkyl;R.sup.9 independently is any of the groups defined for R.sup.4 ;R.sup.
    Type: Grant
    Filed: December 18, 1995
    Date of Patent: December 2, 1997
    Assignee: Zeneca Limited
    Inventor: Roy Bradbury
  • Patent number: 5686585
    Abstract: An azo dye for use in color filters soluble in alkaline aqueous solutions and organic solvents and having in one molecule at least one sulfonamido group of which one hydrogen atom is substituted; and a method for producing a color filter having a plurality of color filter elements which comprises the steps of a) coating a substrate with an organic solvent solution of a photoresist composition containing said azo dye and drying the coat to form an adhering layer, b) exposing a specific part of said layer to radiation ray, c) developing the exposed or unexposed region with alkali to form a colored pattern, and d) repeating the steps a)-c) on every dye of different color present in said composition.
    Type: Grant
    Filed: November 18, 1994
    Date of Patent: November 11, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshiki Hishiro, Naoki Takeyama, Shigeki Yamamoto
  • Patent number: 5681832
    Abstract: Aroylaniline compounds which exhibit anti-retroviral activity, pharmaceutical compositions containing such aroylaniline compounds, and methods for treating a retroviral-infected host comprising administering an antiviral effective amount of an aroylaniline compound to a host.
    Type: Grant
    Filed: February 17, 1995
    Date of Patent: October 28, 1997
    Assignees: The United States of America as represented by the Department of Health and Human Services, Georgia Tech Research Corporation
    Inventors: Rudiger D. Haugwitz, Leon Zalkow, Ewa Gruszecka-Kowalik, Edward Burgess
  • Patent number: 5545725
    Abstract: Disazo dyes are disclosed which are particularly suitable for dyeing paper.Paper is dyed with these dyes in greenish-yellow or yellow to red shades of good fastness properties.
    Type: Grant
    Filed: November 10, 1994
    Date of Patent: August 13, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Adolf K aser, Willy Stingelin
  • Patent number: 5468848
    Abstract: The new basic azo dyestuffs of the formula ##STR1## wherein the symbols have the meaning given in the description, are suitable for dyeing synthetic and naturally occurring substrates which can be dyed with basic dyestuffs.
    Type: Grant
    Filed: June 21, 1994
    Date of Patent: November 21, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karin Hassenruck, Peter Wild
  • Patent number: 5395926
    Abstract: Compounds of formula ##STR1## wherein R is hydrogen or a group ##STR2## M.sub.1 and M.sub.2 are each independently of the other an alkali metal or alkaline earth metal or aluminum or a group of formula ##STR3## wherein n is 1, 2 or 3, and R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are hydrogen or C.sub.1 -C.sub.8 alkyl,X.sub.1 and X.sub.2 are each independently of the other --N.dbd. or --CH.dbd.,Q.sub.1 and Q.sub.2 are each independently of the other radicals of formula ##STR4## These compounds have excellent suitability for pigmenting organic material of high molecular weight, preferably polyolefins, and have superior lightfastness.
    Type: Grant
    Filed: September 22, 1993
    Date of Patent: March 7, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Stefan Hari, Olof Wallquist
  • Patent number: 5391720
    Abstract: Disclosed is an imidazole azo dye of formula (I), which is useful for image formation and as a filter dye, which has a sharp absorption wave and which is fast to light, heat, air, moisture and chemicals. Also disclosed is a thermal transfer dye-donating material containing imidazole azo dye(s) of formula (I) preferably along with aminopyrazole azo dye(s) of formula (II). The material gives a high-density image with good color reproduction, and the image formed has improved storage stability. ##STR1## In (I), B and C independently represent a hydrogen atom or a substituent capable of being substituted in the imidazole ring; A represents an aryl or heterocyclic group; provided that when B is a hydrogen atom, C is not a hydrogen atom nor an alkyl group having from 1 to 3 carbon atoms; provided that when C is a hydrogen atom, B is not a substituted nor unsubstituted alkyl group; provided that C is not a mercapto group or an alkylthio group; and provided that B is not a carboxyl group.
    Type: Grant
    Filed: December 3, 1992
    Date of Patent: February 21, 1995
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hisashi Mikoshiba, Tomomi Tateishi
  • Patent number: 5312906
    Abstract: Bisazo compounds of formula (I), an intermediate for producing the bisazo compound of formula (I), and trisazo compounds of formula (II) for use in optical information recording media, and methods of producing these compounds are disclosed: ##STR1## wherein R represents hydrogen, an alkyl group having 1 to 20 carbon atoms; an aryl group selected from the group consisting of phenyl group, naphthyl group, mesityl group, and tri-t-butyl phenyl group; an alkoxyl group having 1 to 4 carbon atoms; a nitro group; a cyano group; chlorine; or bromine; n is an integer of 1, 2, or 3; and C.sub.p represents a coupler residue.
    Type: Grant
    Filed: July 24, 1992
    Date of Patent: May 17, 1994
    Assignee: Ricoh Company, Ltd.
    Inventor: Masakatsu Shimoda
  • Patent number: 5274084
    Abstract: An azo compound represented by the following general formula IA and an electrophotographic photosensitive member comprising a photosensitive layer containing the azo compound: ##STR1## wherein R.sup.1 and R.sup.2 are the same or different from each other and indicate a hydrogen atom, an alkyl group, an alkenyl group, a hydroxyl group, an alkoxy group, a carboxy group, an alkoxy carbonyl group, an acyl group, an aryl group, a halogen group or a cyano group, respectively; R.sup.14 indicates a hydrogen atom, a halogen group, an alkyl group, an alkoxy group, an aryl group, an amino group, a cyano group, a nitro group or a sulfoxide group; and A indicates a coupler residue having an acceptor property.
    Type: Grant
    Filed: November 24, 1992
    Date of Patent: December 28, 1993
    Assignee: Mita Industrial Co., Ltd.
    Inventors: Eiichi Miyamoto, Yasuyuki Hanatani, Hiroaki Iwasaki, Yasufumi Mizuta, Akihiko Kawahara
  • Patent number: 5097022
    Abstract: An electrophotographic photoconductor comprises an electroconductive support and a photoconductive layer formed thereon comprising a bisazo compound having the formula (I) serving as a charge generating material: ##STR1## wherein Y represents a halogen, an alkyl group which may have a substituent, an alkoxyl group, an acyl group, a substituted amino group, a cyano group or a nitro group; R represents hydrogen, or an alkyl group which may have a substitutent; and Ar represents an aryl group which may have a substituent.
    Type: Grant
    Filed: November 3, 1989
    Date of Patent: March 17, 1992
    Assignee: Ricoh Company, Ltd.
    Inventors: Masaomi Sasaki, Tomoyuki Shimada, Mitsuru Hashimoto
  • Patent number: 5081233
    Abstract: A bisazo compound of the general formula: ##STR1## where Ar is selected from the group consisting of substituents (a) .about. (i), a dinitro compound, a diamino compound, and a tetrazonium salt, which respectively serve as a starting material, a first intermediate and a second intermediate for producing the above bisazo compound are prepared, and an electrophotographic photoconductor comprising an electroconductive support having thereon a photoconductive layer containing any of the above bisazo compounds is disclosed.
    Type: Grant
    Filed: October 24, 1988
    Date of Patent: January 14, 1992
    Assignee: Ricoh Company, Ltd.
    Inventors: Masaomi Sasaki, Tomoyuki Shimada
  • Patent number: 5068319
    Abstract: The present invention relates to dyestuffs soluble in organic solvents having the structure: ##STR1## wherein R is CF.sub.3 or phenyl, R.sub.1 and R.sub.2 are the same or different substituent groups selected from the group consisting of hydrogen, hydroxy, halogen, C.sub.1 to C.sub.3 alkyl and C.sub.1 to C.sub.4 alkoxy, R.sub.3 is selected from the groups consisting of hydrogen, C.sub.1 to C.sub.3 alkyl, C.sub.1 to C.sub.3 alkoxy, COOH, and COOR.sub.5 wherein R.sub.5 is C.sub.1 to C.sub.4 alkyl, R.sub.6 is selected from the group consisting of hydrogen, sulfonyl, C.sub.1 to C.sub.3 alkyl, C.sub.1 to C.sub.3 alkoxy and halogen, and n is zero or a whole number ranging from 1 to 3. The dyestuffs of the invention are useful as light absorbers or antihalation agents in photosensitive compositions. They may also be used as dyeing agents for paper, fibers or films and as components in printing ink formulations.
    Type: Grant
    Filed: March 29, 1990
    Date of Patent: November 26, 1991
    Assignee: Hoechst Celanese Corporation
    Inventors: David M. Brown, Robert E. Potvin
  • Patent number: 5059683
    Abstract: Compounds of the formula ##STR1## and acid addition salts thereof whereinA.sub.1 is C.sub.1-8 alkylene; C.sub.2-8 alkylene substituted by 1 or 2 substituents selected from hydroxy, halo and cyano; C.sub.2-8 alkenylene; cyclohexylene; cyclohexylene substituted by 1 to 3 C.sub.1-4 alkyl groups; phenylene or phenylene substituted by 1 or 2 substituents selected from halo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy,B.sub.1 is ##STR2## wherein the quaternized nitrogen atom is bound to a carbon atom of A.sub.1,R is hydrogen, C.sub.1-4 alkyl, C.sub.5-6 cycloalkyl, phenyl, benzyl or phenylethyl,T is hydrogen, cyano, --COOR.sub.1, --CON(R.sub.2).sub.2, --SO.sub.2 N(R.sub.2).sub.2, ##STR3## wherein R.sub.1 is C.sub.1-6 alkyl or phenyl(C.sub.1-3 alkyl),each R.sub.3 is independently hydrogen, C.sub.1-4 alkyl, --CON(R.sub.2).sub.2 or --N(R.sub.5).sub.2, andX.sub.1 is --S--, --O-- or --N(R.sub.5)--,Y is hydrogen or a chromophoric group, andZ is ##STR4## wherein R.sub.11 is ##STR5## wherein W is --NR.sub.6 R.sub.7 or --.sup..sym.
    Type: Grant
    Filed: May 5, 1989
    Date of Patent: October 22, 1991
    Assignee: Sandoz Ltd.
    Inventors: Helmut A. Moser, Roland Wald
  • Patent number: 5037967
    Abstract: Disperse dyes containing a monoazo coupling component of the formula ##STR1## in which X is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, acylamino, halogen or a group of the formula --NH--CO--NHQ in which Q is hydrogen, C.sub.1 -C.sub.4 alkyl or phenyl,Y is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkoxy,R is hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.12 alkenyl or phenyl, or Y and R, together with the nitrogen atom and the two C atoms linking them, form a 5-membered or 6-membered ring,B is a linear or branched C.sub.2 -C.sub.6 alkylene radical,W is halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy,Z is halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or nitro andm and n are each 0, 1, 2 or 3.
    Type: Grant
    Filed: November 7, 1989
    Date of Patent: August 6, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Angelo D. Casa, Peter Liechti, Max Dempfle
  • Patent number: 4920208
    Abstract: Basic azo dyestuffs of the general formula ##STR1## and tautomers thereof, in which D is the radical of a diazo or tetrazocomponent free of anionic groups,X is O or NH,R.sup.1, R.sup.2 are hydrogen, alkyl or aryl,B is a bridge member andR.sup.3, R.sup.4 are hydrogen, alkyl, alkenyl or aralkyl orR.sup.2 and R.sup.3 together with B and the two nitrogen atoms to which they are bonded form a 5- or 6-membered heterocyclic and in this caseB also stands for a direct bond, orR.sup.3 and R.sup.4 together with the nitrogen atom to which they are bonded form a 5- or 6-membered heterocyclic,n is 1 or 2, and in whichthe cyclic and acyclic radicals can in turn be substituted by radicals customary in dyestuff chemistry, find utility for dyeing and coloring synthetic and natural materials.
    Type: Grant
    Filed: September 28, 1988
    Date of Patent: April 24, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventor: Aloysius Engel
  • Patent number: 4833235
    Abstract: Disazo compounds of the formula ##STR1## and salt thereof, D is the radical of a diazo component of the benzene or naphthalene series.K is the radical of a heterocyclic coupling component of the aminopyrazole-, pyridone- or barbituric acid-series, n is 1 to 4,R.sub.1 is hydrogen, C.sub.1-4 alkyl or substituted C.sub.1-4 alkyl,each of R.sub.2 and R.sub.3 is independently hydrogen, halo, C.sub.1-4 alkyl, substituted C.sub.1-4 alkyl, C.sub.1-4 alkoxy, substituted C.sub.1-4 alkoxy, --NHCO--Rhd 5, amino, substituted amino or a quaternary ammonium group, wherein R.sub.5 is C.sub.1-4 alkyl, substituted C.sub.1-4 alkyl, C.sub.1-4 alkoxy or amino,R.sub.4 is hydrogen, C.sub.1-4 alkyl, C.sub.
    Type: Grant
    Filed: October 7, 1987
    Date of Patent: May 23, 1989
    Assignee: Sandoz Ltd.
    Inventor: Reinhard Pedrazzi
  • Patent number: 4764599
    Abstract: Sulfo-free compounds of the formula ##STR1## where R is hydrogen or C.sub.1 -C.sub.4 -alkyl andK.sup.1 and K.sup.2 independently of one another are a radical of a coupling component, and the rings A and B may furthermore be monosubstituted or polysubstituted by fluorine, chlorine, bromine, nitro, methyl, trifluoromethyl, ethyl, acetyl, benzoyl, a carboxylic ester group, unsubstituted or substituted carbamyl or sulfamyl, an aryl sulfonate group, C.sub.1 -C.sub.4 -alkylsulfonyl, unsubstituted or substituted phenylsulfonyl, cyano or acylamino or a fused ring, are very useful as pigments for coloring printing inks, surface coatings or plastics.
    Type: Grant
    Filed: September 30, 1986
    Date of Patent: August 16, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Colberg, Erwin Hahn
  • Patent number: 4760003
    Abstract: An electrophotographic photosensitive member comprises a photosensitive layer on a substrate, said photosensitive layer comprising a disazo pigment represented by the formula (1).
    Type: Grant
    Filed: May 21, 1986
    Date of Patent: July 26, 1988
    Assignee: Canon Kabushiki Kaisha
    Inventors: Masakazu Matsumoto, Takao Takiguchi, Masataka Yamashita, Shoji Umehara, Shozo Ishikawa, Hajime Miyazaki
  • Patent number: 4742161
    Abstract: Disazo and trisazo compounds of the formula ##STR1## and salts thereof, wherein in each B is independently hydrogen; C.sub.1-4 alkyl; (C.sub.1-4 alkoxy) C.sub.1-4 alkyl; C.sub.2-4 hydroxyalkyl; C.sub.5-6 cycloalkyl; C.sub.5-6 cyloalkyl substituted by 1 to 3 C.sub.1-4 alkyls; phenyl (C.sub.1-3 alkyl); phenyl (C.sub.1-3 alkyl) the phenyl group of which is substituted by 1 to 3 substituents selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy and halo; --A--NH--R.sub.2 ; --A.sub.2 --N(R.sub.7).sub.2 ; --A.sub.N.sup..crclbar. (R.sub.8).sub.2 R.sub.9 A.sup..sym. or --N(R.sub.7).sub.2,whereinA, A.sub.1, A.sub.2 and R.sub.7 -R.sub.9 are as defined in the specification,each R is independently hydrogen; amino C.sub.1-4 alkyl; C.sub.5-6 cycloalkyl; C.sub.5-6 cycloalkyl substituted by 1 or 2 C.sub.1-4 alkyls; phenyl; benzyl; phenylethyl; or phenyl, benzyl or phenylethyl the phenyl group of which is substituted by 1 or 2 substituents selected from methyl, ethyl, methoxy and ethoxy,each R.sub.5 is independently hydrogen or C.
    Type: Grant
    Filed: May 20, 1985
    Date of Patent: May 3, 1988
    Assignee: Sandoz Ltd.
    Inventor: Jacky Dore
  • Patent number: 4739042
    Abstract: Halftone gravure printing inks containing pyridone azo dyestuffs wherein the dyestuffs are obtained by reacting a pyridone dyestuff of the formula ##STR1## with a dicarboxylic or polycarboxylic acid or a pyridone azo dyestuff of the formula ##STR2## with a dihydroxy or polyhydroxy compound.
    Type: Grant
    Filed: August 4, 1986
    Date of Patent: April 19, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Lorenz, Artur Haus
  • Patent number: 4663442
    Abstract: A disazo compound, having the general formula, ##STR1## wherein Y represents a substituted or non-substituted cyclic hydrocarbon or substituted or non-substituted heterocycle; R represents hydrogen, substituted or non-substituted alkyl group, or substituted or non-substituted phenyl group; andZ represents a substituted or non-substituted cyclic hydrocarbon or heterocycle fused with phenyl nucleus.
    Type: Grant
    Filed: July 18, 1985
    Date of Patent: May 5, 1987
    Assignee: Ricoh Co., Ltd.
    Inventor: Masafumi Ohta
  • Patent number: 4634764
    Abstract: Compounds of the formula ##STR1## wherein each R is independently --N(R.sub.1).sub.2, --N.sup..sym. (R.sub.2).sub.3 A.sup..crclbar. or hydroxy, whereineach R.sub.1 is independently hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl or aryl orboth R.sub.1 's taken together and with the nitrogen atom to which they are attached form a 5- or 6-membered saturated heterocyclic ring,each R.sub.2 is independently alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl or aryl ortwo R.sub.2 's taken together and with the nitrogen atom to which they are attached form a 5- or 6-membered saturated heterocyclic ring orall three R.sub.2 's taken together and with the nitrogen atom to which they are attached form a 5- or 6-membered unsaturated heterocyclic ring, andA.sup..crclbar. is a non-chromophoric anion,each T is independently a bridging radical, andZ is hydrogen or --N.dbd.
    Type: Grant
    Filed: November 10, 1983
    Date of Patent: January 6, 1987
    Assignee: Sandoz Ltd.
    Inventor: Manfred Greve
  • Patent number: 4631242
    Abstract: An electrophotographic material comprises a conductive support and a light-sensitive layer containing at least one of the azo compound of the formulas [I]-[III]:formula [I]:Cp.sub.1 --N.dbd.N--A--N.dbd.N--Cp.sub.2A represents a divalent residue which bonds through C atoms to N atoms which constitute azo and Cp.sub.1 is a group of by the formula: ##STR1## Z represents a substituted or unsubstituted carbocyclic aromatic ring, a substituted or unsubstituted heterocyclic aromatic ring or a unsaturated monocyclic hydrocarbon ring and R represents an aryl group containing one or two CF.sub.3 groups and Cp.sub.2 is a coupler residue different from said Cp.sub.1 and is selected from following formulas (a)-(f): ##STR2## Z.sup.1 and Z.sup.2 represent a substituted or unsubstituted aromatic hydrocarbon ring or substituted or unsubstituted hetero ring, R.sup.1 and R.sup.2 represent substituted or unsubstituted alkyl, aralkyl, aryl or hetero ring group, R.sup.3 represents an alkyl or carboxyl group or an ester thereof, R.
    Type: Grant
    Filed: September 5, 1985
    Date of Patent: December 23, 1986
    Assignee: Mitsubishi Paper Mills, Ltd.
    Inventors: Kazuhiro Emoto, Kozo Haino, Akira Itoh
  • Patent number: 4623720
    Abstract: 1:1 and 1:2 metal complexes comprising the unit of the formula ##STR1## wherein A and B, independently, are radicals of diazo or coupling components, with the proviso that when one of A and B is a radical of a diazo component, the other is a radical of a coupling component,T is --SO.sub.2 N(R.sub.1)-- or --N(R.sub.1)SO.sub.2 --, wherein R.sub.1 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkyl substituted by phenyl or carboxy or C.sub.2-4 alkyl substituted in the .beta.--, .gamma.-- or .delta.--position by phenoxy, C.sub.1-4 alkyl, chloro or hydroxy, with the proviso that T is --N(R.sub.1)SO.sub.2 -- when A is the radical of a diazo component and T is --SO.sub.2 N(R.sub.
    Type: Grant
    Filed: June 4, 1981
    Date of Patent: November 18, 1986
    Assignee: Sandoz Ltd.
    Inventor: Herbert Holliger
  • Patent number: 4582771
    Abstract: This invention relates to a disazo compound, a method for producing said disazo compound and an electrophotographic element containing said disazo compound, said disazo compound has the general formula (I), ##STR1## wherein Y represents a substituted or non-substituted cyclic hydrocarbon or substituted or non-substituted heterocycle; R represents hydrogen, substituted or non-substituted alkyl group, or substituted or non-substituted phenyl group; and Z represents a substituted or non-substituted cyclic hydrocarbon or heterocycle fused with phenyl nucleus.
    Type: Grant
    Filed: December 28, 1984
    Date of Patent: April 15, 1986
    Assignee: Ricoh Co., Ltd.
    Inventor: Masafumi Ohta
  • Patent number: 4562249
    Abstract: There are described novel yellow to red azo compounds of the formula I ##STR1## wherein each D independently of the other is the radical of an aromatic or heterocyclic diazo component, each Z independently of the other is hydrogen or a C.sub.1 -C.sub.4 -alkyl group or an acylamino group, Y is hydrogen or an unsubstituted or substituted C.sub.1 -C.sub.6 -alkyl group, X is either the direct bond or C.sub.1 -C.sub.6 -alkylene, ##STR2## and n is a number from 2 to 6, preferably 2; and the substituent Y, in the case of an unsubstituted or substituted C.sub.1 -C.sub.6 -alkyl group, can also be bonded to the o-position relative to the N atom of the phenylene group to form a six-membered ring, or both Y substituents can be linked together to form a C.sub.1 -C.sub.
    Type: Grant
    Filed: March 5, 1985
    Date of Patent: December 31, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Hansrudolf Schwander, Rudolf Hurter
  • Patent number: 4540643
    Abstract: The present invention provides a tetrazoneum salt compound represented by the general formula (I): ##STR1## (wherein, X stands for an anion functional group.); a disazo compound represented by the general formula (II): ##STR2## (wherein, R stands for an alkyl group, an alkoxy group, a nitro group, halogen, a cyano group or a halomethyl group, n stands for an integer of 0, 1, 2 or 3, and in case n is an integer of 2 or 3 R may be the same or different.); a method for the production thereof, and electrophotographic elements using the same or like disazo compounds as the charge carrier generating materials.
    Type: Grant
    Filed: April 9, 1984
    Date of Patent: September 10, 1985
    Assignee: Ricoh Co., Ltd.
    Inventor: Kyoji Tsutsui
  • Patent number: 4537844
    Abstract: A novel disazo compound is provided which is represented by the general formula (I): ##STR1## (wherein, R.sub.1 and R.sub.2 each stands for hydrogen, a lower alkyl group with 1-4 carbon atoms, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aromatic group, or a substituted or unsubstituted hetero ring group. R.sub.1 and R.sub.2 may be the same or different. And, R.sub.1 and R.sub.2 may mutually bond to form a ring).This disazo compound may be obtained by diazotating 2,6-diaminoanthraquinone and reacting the same with a coupler represented by the general formula (IV): ##STR2## (wherein, R.sub.1 and R.sub.2 are the same as defined above). Further, a multilayer type electrophotographic element is provided which comprises a charge carrier generating layer and a charge transfer layer and uses, as a charge carrier generating substance, a disazo compound represented by the general formula (I).
    Type: Grant
    Filed: September 28, 1983
    Date of Patent: August 27, 1985
    Assignee: Ricoh Co. Ltd.
    Inventor: Mitsuru Hashimoto
  • Patent number: 4536570
    Abstract: This invention relates to novel mixtures consisting essentially of benzanilide bridged disazo compounds which are randomly substituted with x (N-substituted sulfonamido) groups, to acid-addition salts of said disazo compounds, useful as direct dyes particularly in the dyeing of cellulose, and to methods of preparation of said mixtures of (N-substituted sulfonamido) substituted disazo compounds.
    Type: Grant
    Filed: October 25, 1982
    Date of Patent: August 20, 1985
    Assignee: The Hilton-Davis Chemical Co.
    Inventor: Nathan N. Crounse
  • Patent number: 4500619
    Abstract: An electrophotographic photosensitive member comprises a layer containing at least one disazo pigment represented by the formula: ##STR1## wherein R.sub.1 and R.sub.2 each represent hydrogen, halogen, lower alkyl or lower alkoxy; R.sub.3 represents methyl, ehtyl or C.sub.3 -C.sub.10 linear alkyl; and X represents a residue necessary to complete an aromatic hydrocarbon ring or heterocyclic ring, substituted or unsubstituted.
    Type: Grant
    Filed: March 22, 1984
    Date of Patent: February 19, 1985
    Assignees: Copyer Kabushiki Kaisha, Canon Kabushiki Kaisha
    Inventors: Shozo Ishikawa, Kazuharu Katagiri, Katsunori Watanabe, Kiyoshi Sakai, Makoto Kitahara
  • Patent number: 4483796
    Abstract: Disazo and polyazo compounds of the formula ##STR1## wherein each A is independently ##STR2## and each R.sub.3 is independently C.sub.1-4 alkyl, oreach A, R.sub.3 and the ##STR3## radical to which they are attached, taken together, independently, are ##STR4## wherein each R.sub.21 is independently halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,p is 0, 1 or 2,the * denotes the carbon atom attached to the --N.dbd.N-- radical, andthe ** denotes the carbon atom attached to X,each R.sub.1 and the ##STR5## radical to which it is attached taken together, independently, are the radical of an aromatic or heterocyclic coupling component,each A.sub.1 and A.sub.2 taken together are --O--Me--O--, wherein Me is copper, cobalt, iron, nickel, manganese or zinc, oreach A.sub.1 is hydroxy, andeach A.sub.2 is independently hydrogen, hydroxy or C.sub.1-4 alkoxy,X is a direct bond or a bridging radical,each Y is independently a direct bond, C.sub.1-4 alkylene, --CO--NH--(CH.sub.2).sub.m --, --NH--CO--(CH.sub.2).sub.m -- or --SO.sub.
    Type: Grant
    Filed: August 18, 1982
    Date of Patent: November 20, 1984
    Assignee: Sandoz Ltd.
    Inventors: Paul Doswald, Emil Moriconi, Helmut Moser, Horst Schmid