Stilbene Containing Patents (Class 534/689)
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Patent number: 8940059Abstract: Disclosed is an azo compound represented by the formula (1) below, a salt thereof, or a copper complex salt compound thereof. (In the formula, R1 and R2 independently represent a hydrogen atom, a sulfonic acid group, a lower alkyl group or a lower alkoxyl group; R3-R6 independently represent a hydrogen atom, a lower alkyl group or a lower alkoxyl group; R7 represents a lower alkyl group or a lower alkoxyl group; and n represents 0 or 1.Type: GrantFiled: December 21, 2010Date of Patent: January 27, 2015Assignees: Nippon Kayaku Kabushiki Kaisha, Polatechno Co., Ltd.Inventors: Yuichi Sadamitsu, Takahiro Higeta
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Patent number: 8771378Abstract: Disclosed is an azo compound represented by the general formula (1) or a salt thereof: wherein R1 and R2 independently represent a hydrogen atom, a lower alkyl group or a lower alkoxy group; and n represents 1 or 2. Also disclosed are a dye-containing polarizing film and a dye-containing polarizing plate, each of which comprises a polarizing film base material and the azo compound contained in the base material.Type: GrantFiled: November 17, 2010Date of Patent: July 8, 2014Assignees: Nippon Kayaku Kabushiki Kaisha, Polatechno Co., Ltd.Inventors: Yuichi Sadamitsu, Takuto Nishiguchi, Hiroaki Ohno
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Patent number: 8541557Abstract: 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: GrantFiled: June 15, 2012Date of Patent: September 24, 2013Assignee: Ricoh Company, Ltd.Inventor: Masafumi Ohta
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Patent number: 8309696Abstract: 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: GrantFiled: August 31, 2009Date of Patent: November 13, 2012Assignee: Canon Kabushiki KaishaInventors: Atsushi Fujii, Mai Murakami
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Publication number: 20120253025Abstract: 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: ApplicationFiled: June 15, 2012Publication date: October 4, 2012Applicant: RICOH COMPANY, LTD.Inventor: Masafumi OHTA
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Patent number: 7931702Abstract: Disclosed is an azo compound represented by the general formula (1) or a salt thereof: wherein R1 and R2 independently represent a hydrogen atom, a lower alkyl group or a lower alkoxy group; and n represents 1 or 2. Also disclosed are a dye-containing polarizing film and a dye-containing polarizing plate, each of which comprises a polarizing film base material and the azo compound contained in the base material.Type: GrantFiled: May 24, 2007Date of Patent: April 26, 2011Assignees: Nippon Kayaku Kabushiki Kaisha, Polatechno Co., Ltd.Inventors: Yuichi Sadamitsu, Takuto Nishiguchi, Hiroaki Ohno
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Publication number: 20100075239Abstract: 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: ApplicationFiled: August 31, 2009Publication date: March 25, 2010Applicant: CANON KABUSHIKI KAISHAInventors: Atsushi Fujii, Mai Murakami
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Publication number: 20070190269Abstract: The present invention relates to a azo dyestuff compound of the following formula (I), of which the free acid is represented by the following formula: wherein R1, R2, R3, R4, and n are defined as in the specification. The azo dyestuff compound of formula (I) of the present invention is used for preparing polarizing film. The present invention also relates to a polarizing film comprising the azo dyestuff compound of formula (I), which has excellent degree of polarization.Type: ApplicationFiled: September 12, 2006Publication date: August 16, 2007Applicant: Everlight USA, Inc.Inventor: Ming-Chin Cheng
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Patent number: 7078497Abstract: The dyes of formula (1) according to claim 1 and the copper complexes of dyes of formula (2) according to claim 9 or the mixtures of mono-copper complex with the bis-copper complex are excellently suitable for dyeing paper with good light-fastness properties.Type: GrantFiled: December 19, 2001Date of Patent: July 18, 2006Assignee: Ciba Specialty Chemicals CorporationInventors: Adolf Käser, Holger Lautenbach
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Patent number: 6861106Abstract: Dichroic dyes, dichroic dye compositions, and liquid crystal composition and liquid crystal display element containing the dichroic dyes. The dichroic dye has increased solubility and stability.Type: GrantFiled: May 23, 2003Date of Patent: March 1, 2005Assignee: Industrial Technology Research InstituteInventors: Shih-Hsien Liu, Yang-Chu Lin, Woan-Shiow Tzeng, Jie-Hwa Ma, Kung-Lung Cheng, Long-Li Lai
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Patent number: 6790490Abstract: This invention relates to a polyvinyl alcohol type polarizing film or plate which comprises a water-soluble dye having the formula (1) in a free acid form or a copper complex salt thereof. The said polarizing plate has excellent polarizing performance capability and durability, and is suitably used for the green channel of a liquid crystal projector when B in formula (1) is a benzoylamino group and the water-soluble dye has a wavelength for maximum absorption (&lgr;max) of 520 nm or more and less than 580 nm.Type: GrantFiled: December 17, 2001Date of Patent: September 14, 2004Assignee: Nippon Kayaku Kabushiki KaishaInventors: Shoji Oiso, Kumiko Ishii, Yoshitaka Kajiwara, Toru Tabei
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Publication number: 20040135117Abstract: Dichroic dyes, dichroic dye compositions, and liquid crystal composition and liquid crystal display element containing the dichroic dyes. The dichroic dye has increased solubility and stability.Type: ApplicationFiled: May 23, 2003Publication date: July 15, 2004Applicant: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTEInventors: Shih-Hsien Liu, Yang-Chu Lin, Woan-Shiow Tzeng, Jie-Hwa Ma, Kung-Lung Cheng, Long-Li Lai
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Patent number: 6464768Abstract: The invention relates to a dye in which R1 is hydrogen, alkyl of 1 to 4 carbon atoms, or alkoxy of 1 to 4 carbon atoms; R2 is hydrogen, carboxyl, chloro or nitro; R21 is hydrogen; or R2 and R21 together form a benzene ring which is fused on in positions 3 and 4 of the ring A and can carry 1, 2 or 3 sulfo groups; m is a number from 0 to 1; n is a number from 1 to 2; M+ is a cation or a mixture of different cations, at least one equivalent of the cations M+ per mole of the dye being lithium cations and/or cations of the formula (II) where p is a number from 1 to 30; X is CH2CH2, CH(CH3)CH2, CH2CH(CH3) or a combination thereof and R3, R4 and R5 independently of one another are hydrogen, a group of the formula (III) —(—X—O—)pH (III) or an aliphatic radical of 1 to 18 carbon atoms. Dyes of the formula (I) are particularly suitable as colorants in inkjet inks.Type: GrantFiled: July 12, 1999Date of Patent: October 15, 2002Assignee: Clariant GmbHInventors: Wolfgang Bauer, Heidemarie Menzel, Josef Geisenberger, Reinhard Pedrazzi
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Patent number: 6448384Abstract: An electrophotographic photoconductor has an electroconductive support, and a photoconductive layer formed thereon which contains at least one bisazo compound of formula (I): wherein Cp1 and Cp2 are each a coupler radical which may be the same or different. Further, these are disclosed a bisazo compound of formula (II), and raw materials thereof, that is, 1,4-bis[4-(4-nitrophenyl)-1,3-butadienyl]benzene of formula (V), 1,4-bis[4-(4-aminophenyl)-1,3-butadienyl]benzene of formula (VI) and a bis(diazonium salt) compound of formula (III).Type: GrantFiled: September 4, 2001Date of Patent: September 10, 2002Assignee: Ricoh Company, Ltd.Inventor: Tomoyuki Shimada
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Patent number: 6365719Abstract: Compounds of formula (I) with the meanings of D, R1, R2, X and Y as given in claim 1 can be used as paper dyes or direct dyes or for the preparation of ink-jet inks.Type: GrantFiled: March 27, 2000Date of Patent: April 2, 2002Assignee: Clariant Finance (BVI) LimitedInventor: Friedrich Lehr
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Patent number: 6140477Abstract: A polyazo compound capable of effectively absorbing near-infrared rays, which can be produced from readily available raw materials is provided, which comprises at least one --OH group or at least one group derived from --OH group at p-position of the azo group in the molecule of the polyazo compound. This compound can be produced by diazotizing a substituted or nonsubstituted aromatic monocyclic or polycyclic compound or heterocyclic compound, each having a diazotizable primary amino group, and successively coupling the resulting diazo component with an azo component having a diazotizable primary amino group, the last azo component being such that --OH group or a group derived from --OH group be present at p-position to the azo group resulting from the azo component.Type: GrantFiled: March 23, 1999Date of Patent: October 31, 2000Assignee: Hakkol Chemical Co., Ltd.Inventors: Shigekazu Matsumoto, Takao Yanagisawa, Shigehiro Matsumoto, Kunio Shimabukuro
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Patent number: 6114512Abstract: Oligomeric azo dyes having an alternating construction made up of diazo components and coupling components, containing in the molecule at least 3 units of the structure I--[D--K]-- (I)where D is a tetrazo component of the formula II ##STR1## where x is a direct bond, oxygen, sulfur or a bridge member of the formula --NHCO--, --NHCONH--, --CO--, --NHSO.sub.2 --, --SO.sub.2 NHSO.sub.2 --, --SO.sub.2 --, --SO.sub.2 --NH--A--NH--SO.sub.2 --, -NAlk-CO-, -NAlk-CO-NAlk-, -NAlk-CO--NH--, -NAlk-SO.sub.2 --, --SO.sub.2 -NAlk-SO.sub.2 --, --SO.sub.2 -NAlk-A-NAlk-SO.sub.2 --, --SO.sub.2 -NAlk-A-NH--SO.sub.2 --, --CH.dbd.CH--, --CH.sub.2 CH.sub.2 --, --C(CH.sub.3).sub.2 --, --CH.sub.2 -- or --NH--,R.sup.1 and R.sup.2 are each independently of the other hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkanoyl, cyano, carboxyl, hydroxysulfonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, hydroxyl, carbamoyl, mono- or di-(C.sub.1 -C.sub.4)-alkyl-carbamoyl, sulfamoyl, mono- or di-(C.sub.1 -C.sub.Type: GrantFiled: September 17, 1999Date of Patent: September 5, 2000Assignee: BASF AktiengesellschaftInventors: Gunter-Rudolf Schroder, Torsten Freund, Udo Mayer, Karl-Heinz Etzbach
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Patent number: 6036760Abstract: Aqueous liquid dye concentrates comprising, based on the weight of the concentrate, from 15 to 35% by weight of a dye quantity, from 90 to 100% by weight of the dye quantity consisting of the dye of the formula ##STR1## where Kat.sym. is the equivalent of a tertiary alkylalkanolammonium cation, are useful in the inkjet process.Type: GrantFiled: October 31, 1997Date of Patent: March 14, 2000Assignee: BASF AktiengesellschaftInventor: Rudolf Bermes
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Patent number: 6005085Abstract: The present invention provides novel condensed azo compounds using bisamide compounds of 2-hydroxynaphthalene-3,6-dicarboxylic acid, amide, or ester as the couplers, which have excellent properties such as excellent water resistance, chemical resistance, solvent resistance, and heat resistance.Type: GrantFiled: November 18, 1998Date of Patent: December 21, 1999Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Masaya Kitayama, Kenji Minami, Hiroyuki Wakamori, Katsunori Tanikawa
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Patent number: 5965715Abstract: The invention provides novel bisazo compounds which is obtained by coupling two molecules of a 2-hydroxynaphthalene-3,6-dicarboxylic acid derivative and a compound having two diazo groups in its molecule, as well as a process for producing the same. The present compounds are superior in resistance to water, chemical agents, solvents, heat and the like.Type: GrantFiled: June 22, 1998Date of Patent: October 12, 1999Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Masaya Kitayama, Kenji Minami, Hiroyuki Wakamori
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Patent number: 5952477Abstract: The present invention is concerned with a novel azo compound represented by formula (1), (2) or (3), a water-soluble dye comprising this azo compound, and a polarizing film containing this azo compound. The obtained polarizing film has high hydrothermoresistance and a high polarization degree and is excellent in optical characteristics: ##STR1## wherein each of the groups is defined.Type: GrantFiled: October 15, 1997Date of Patent: September 14, 1999Assignee: Mitsui Chemicals, Inc.Inventors: Tsutami Misawa, Akira Ogiso, Rihoko Imai, Hisato Itoh
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Patent number: 5891227Abstract: Aqueous dye preparations useful for producing inks for the inkjet process or writing inks or for producing aqueous alcoholic coating or printing colors comprise, based on the weight of the preparation, from 0.1 to 15% by weight of a dye quantity comprising from 90 to 100% by weight of the dye of the formula I ##STR1## where Kat.sup..sym. is the equivalent of a metal or ammonium ion, from 1 to 40% by weight of carbon black and from 0.1 to 15% by weight of polyethylene glycol.Type: GrantFiled: August 14, 1997Date of Patent: April 6, 1999Assignee: BASF AktiengesellschaftInventors: Dietrich Hoffmann, Ulrike Schlosser, Erwin Czech, Walter Kurtz, Karin Heidrun Beck, Doug R. Campbell, Helmut Bellaire, Horst Belde
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Patent number: 5883233Abstract: This invention relates to a dye having the formula (I) ##STR1## wherein each M is a hydrogen ion, an alkali metal ion, or R.sup.a R.sup.b R.sup.c R.sup.d N.sup.+ (where R.sup.a, R.sup.b, R.sup.c and R.sup.d are independently hydrogen, C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 hydroxyalkyl). This invention further relates to the use of the dye.Type: GrantFiled: July 24, 1998Date of Patent: March 16, 1999Assignee: Bayer CorporationInventors: Joseph C. Catlin, Richard H. Kokel
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Patent number: 5739298Abstract: Novel azo compounds having the specific structural formula (1) or (3) set out below, water-soluble dyes containing the compounds, and polarizing films containing the water-soluble dyes: ##STR1## wherein R.sub.1 represents a hydrogen or halogen atom or a hydroxyl, C.sub.1-2 alkyl, C.sub.1-2 alkoxyl, C.sub.1-2 acylamino, cyano, carboxyl or sulfonic acid group; R.sub.3 and R.sub.8 individually represent a hydrogen atom or a hydroxyl, C.sub.1-2 alkyl or C.sub.1-2 alkoxyl group; R.sub.2 and R.sub.4 individually represent a hydrogen atom or a hydroxyl, C.sub.1-2 alkyl, C.sub.1-2 alkoxyl or C.sub.1-2 acylamino group; R.sub.5 represents a hydrogen atom or a carboxyl or C.sub.1-2 alkoxyl group; R.sub.6 represents a hydrogen atom, a hydroxyl, amino, methylamino, .beta.-hydroxyethylamino or C.sub.1-2 acylamino group, or a phenylamino or benzoylamino group which the phenyl nucleus may be substituted by one or more nitro, amino, hydroxyl, C.sub.1-2 alkyl, carboxyl and/or sulfonic acid groups and/or chlorine atoms; R.sub.Type: GrantFiled: June 5, 1996Date of Patent: April 14, 1998Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tsutami Misawa, Akira Ogiso, Rihoko Imai, Hisato Itoh
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Patent number: 5646257Abstract: The new dyestuffs of the formula (I) ##STR1## wherein the substituents R and R.sup.1 and the index n have the meaning given in the description, are outstandingly suitable for dyeing and printing cellulose-containing materials, in particular for the preparation of recording liquids for ink jet recording systems.Type: GrantFiled: November 18, 1994Date of Patent: July 8, 1997Assignee: Bayer AktiengesellschaftInventors: Karin Hassenruck, Karl-Heinz Reinhardt, Peter Wild, Klaus Wunderlich
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Patent number: 5623062Abstract: An electrophotographic photoconductor is disclosed, which comprises an electroconductive support and a photoconductive layer formed thereon comprising a bisazo pigment having the formula (I) serving as a charge generating material: ##STR1## wherein Ar represents a residual group of a coupler represented by ArH selected from the group consisting of: an aromatic hydrocarbon compound having a hydroxyl group, a heterocyclic compound having a hydroxyl group, an aromatic hydrocarbon compound having an amino group, a heterocyclic compound having an amino group, an aromatic hydrocarbon compound having a hydroxyl group and an amino group, a heterocyclic compound having a hydroxyl group and an amino group, an aliphatic compound having an enolic ketone group, and an aromatic hydrocarbon compound having an enolic ketone group. Further, charge generating materials and novel bisazo pigments for use in the electrophotographic photoconductor are disclosed.Type: GrantFiled: April 28, 1994Date of Patent: April 22, 1997Assignee: Ricoh Company, Ltd.Inventors: Masaomi Sasaki, Tomoyuki Shimada
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Patent number: 5569749Abstract: An organic photoconductive material is represented by the following general formula [1]:A.sub.1 --N.dbd.N--B--N.dbd.N--A.sub.2 [1],wherein B is a divalent organic group bonded to nitrogen atoms forming azo groups, A.sub.1 and A.sub.2 are groups different from each other, A.sub.1 is represented by the following general formula [A1]: ##STR1## wherein X is an atomic group which is necessary for forming an aromatic hydrocarbon ring or an aromatic hetero-ring by condensation with the benzene ring, Y is a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, m is an integer of 1 to 4, R is an aromatic hydrocarbon ring group or an aromatic hetero-ring group and n is 1 or 2, and A.sub.2 is a group represented by one of the following general formulae [A2] and [A3]: ##STR2## wherein a.sub.1 is a group selected from R, --N.dbd.CH--R and ##STR3## R, X, Y, m and n are the same as those in the general formula [A1] and p is 0 or 1.Type: GrantFiled: January 18, 1996Date of Patent: October 29, 1996Assignee: Dainichiseika Color & Chemicals Mfg. Co., Ltd.Inventors: Hisao Kouno, Shyouichi Takahashi, Kazuhiro Higashide, Nakaji Komiyama, Osamu Suda, Masaru Hasegawa
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Patent number: 5548073Abstract: Novel azo compounds having the specific structural formula (1) or (3) set out below, water-soluble dyes containing the compounds, and polarizing films containing the water-soluble dyes: ##STR1## wherein R.sub.1 represents a hydrogen or halogen atom or a hydroxyl, C.sub.1-2 alkyl, C.sub.1-2 alkoxyl, C.sub.1-2 acylamino, cyano, carboxyl or sulfonic acid group; R.sub.3 and R.sub.8 individually represent a hydrogen atom or a hydroxyl, C.sub.1-2 alkyl or C.sub.1-2 alkoxyl group; R.sub.2 and R.sub.4 individually represent a hydrogen atom or a hydroxyl, C.sub.1-2 alkyl, C.sub.1-2 alkoxyl or C.sub.1-2 acylamino group; R.sub.5 represents a hydrogen atom or a carboxyl or C.sub.1-2 alkoxyl group; R.sub.6 represents a hydrogen atom, a hydroxyl, amino, methylamino, .beta.-hydroxyethylamino or C.sub.1-2 acylamino group, or a phenylamino or benzoylamino group which the phenyl nucleus may be substituted by one or more nitro, amino, hydroxyl, C.sub.1-2 alkyl, carboxyl and/or sulfonic acid groups and/or chlorine atoms; R.sub.Type: GrantFiled: March 15, 1995Date of Patent: August 20, 1996Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tsutami Misawa, Akira Ogiso, Rihoko Imai, Hisato Itoh
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Patent number: 5536818Abstract: A dichroic dye represented by the formula (I) or (II): ##STR1## wherein the substituents are as described in the specification. The dichroic dyes (I) and (II) exhibit excellent dichroism and can be prepared from 2,2'-ditrifluoromethylbenzidine having no toxicity, such as mutagenicity.Type: GrantFiled: November 4, 1994Date of Patent: July 16, 1996Assignee: Mitsubishi Chemical CorporationInventors: Masaharu Kaneko, Hisayo Ishio
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Patent number: 5506346Abstract: An organic photoconductive material is represented by the following general formula [1]:A.sub.1 -N.dbd.N-B-N.dbd.N-A.sub.2 [1],wherein B is a divalent organic group bonded to nitrogen atoms forming azo groups, A.sub.1 and A.sub.2 are groups different from each other, A.sub.1 is represented by the following general formula [A1]: ##STR1## wherein X is an atomic group which is necessary for forming an aromatic hydrocarbon ring or an aromatic hetero-ring by condensation with the benzene ring, Y is a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, m is an integer of 1 to 4, R is an aromatic hydrocarbon ring group or an aromatic hetero-ring group and n is 1 or 2, and A.sub.2 is a group represented by one of the following general formulae [A2] and [A3]: ##STR2## wherein a.sub.1 is a group selected from R, -N.dbd.CH-R and ##STR3## R, X, Y, m and n are the same as those in the general formula [A1] and p is 0 or 1.Type: GrantFiled: February 28, 1994Date of Patent: April 9, 1996Assignee: Dainichiseika Color & Chemicals Mfg. Co., Ltd.Inventors: Hisao Kouno, Shyouichi Takahashi, Kazuhiro Higashide, Nakaji Komiyama, Osamu Suda, Masaru Hasegawa
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Patent number: 5431723Abstract: Useful for the ink jet process are dye preparations which contain from 0.01 to 10% by weight, based on the weight of the preparation, of a dye quantity which is from 90 to 100% by weight the dye of the formula I ##STR1## where Kat.sym. is the equivalent of a metal or ammonium ion, from 0 to 15% by weight, based on the weight of the preparation, of one or more water-miscible organic solvents, and from 75 to 99.99% by weight, based on the weight of preparation, of water and which are essentially free of foreign salts, in the ink jet process.Type: GrantFiled: July 30, 1993Date of Patent: July 11, 1995Assignee: BASF AktiengesellschaftInventors: Rudolf Bermes, Rainer Dyllick-Brenzinger, Karin H. Beck
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Patent number: 5423100Abstract: Novel azo compounds having the specific structural formula (1) or (3) set out below, water-soluble dyes containing the compounds, and polarizing films containing the water-soluble dyes: ##STR1## wherein R.sub.1 represents a hydrogen or halogen atom or a hydroxyl, C.sub.1-2 alkyl, C.sub.1-2 alkoxy, C.sub.1-2 acylamino, cyano, carboxyl or sulfonic acid group; R.sub.3 and R.sub.8 individually represent a hydrogen atom or a hydroxyl, C.sub.1-2 alkyl or C.sub.1-2 alkoxy group; R.sub.2 and R.sub.4 individually represent a hydrogen atom or a hydroxyl, C.sub.1-2 alkyl, C.sub.1-2 alkoxy or C.sub.1-2 acylamino group; R.sub.5 represents a hydrogen atom or a carboxyl or C.sub.1-2 alkoxy group; R.sub.6 represents a hydrogen atom, a hydroxyl, amino, methylamino, .beta.-hydroxyethylamino or C.sub.1-2 acylamino group, or a phenylamino or benzoylamino group which the phenyl nucleus may be substituted by one or more nitro, amino, hydroxyl, C.sub.1-2 alkyl, carboxyl and/or sulfonic acid groups and/or chlorine atoms; R.sub.Type: GrantFiled: July 23, 1993Date of Patent: June 13, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tsutami Misawa, Akira Ogiso, Rihoko Imai, Hisato Itoh
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Patent number: 5360472Abstract: Disclosed are dye compositions of the formula ##STR1## wherein Cp and Cp' are each coupler compounds of the formula ##STR2## wherein the --COOH group and the --OH group can be in any position on either ring, provided that in the naphthalene ring system there is present least one hydrogen activated through resonance by the --OH group for an electrophilic aromatic substitution coupling reaction, n represents the number of substituents on the rings and is a number of from 0 to 8, and R represents the substituent groups on the ring, wherein each R is independently selected from the group consisting of hydroxyl groups, alkyl groups, substituted alkyl groups, aryl groups, substituted aryl groups, aryl-alkyl groups, substituted aryl-alkyl groups, halogen atoms, and nitro groups. Also disclosed are aqueous ink compositions containing the dyes, processes for making the dyes, processes for making the inks containing the dyes, and printing processes employing the inks.Type: GrantFiled: July 26, 1993Date of Patent: November 1, 1994Assignee: Xerox CorporationInventors: Edward J. Radigan, Jr., Louis V. Isganitis, Warren E. Solodar, Kurt B. Gundlach
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Patent number: 5340504Abstract: The invention relates to light-polarizing films based on water-soluble organic polymers, more particularly polyvinyl alcohol (PVAL), which contain one or more dichroic bis-, tris- or tetrakis-azo dyes.Type: GrantFiled: February 23, 1993Date of Patent: August 23, 1994Assignee: Bayer AGInventor: Uwe Claussen
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Patent number: 5272259Abstract: Dyestuffs which in the form of the free acid conform to the formula ##STR1## in which X and Y independently represent --N.dbd.N--R, --CF.sub.3, --CONH.sub.2, --CONHR.sup.1, --CONR.sup.1 R.sup.2, --COOH, --COOR.sup.1, --CN, --NO.sub.2, --NH.sub.2, --NHR.sup.1, --NR.sup.1 R.sup.2, --OH, --OR.sup.1, --R.sup.1 CONH--, --O--CO--R.sup.1, halogen or a substituted or unsubstituted heterocyclic radical, provided that at least one of the radicals X or Y represents --N.dbd.N--R, in whichR represents an aryl or heterocyclic radical, andR.sup.1 and R.sup.2 independently represent alkyl, cycloalkyl, aryl or aralkyl, which are uninterrupted or interrupted by O, S or both O and S,and in which furthermore the radicals mentioned for R, R.sup.1 and R.sup.Type: GrantFiled: May 26, 1992Date of Patent: December 21, 1993Assignee: Bayer AktiengesellschaftInventors: Uwe Claussen, Friedrich W. Krock
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Patent number: 5262330Abstract: A chromogenic compound found to be especially selective in the determination of calcium in blood of the general formula (I): ##STR1## where: R is hydrogen or lower alkyl;X is CH.sub.2, CH.sub.2 CH.sub.2, CH.dbd.CH, O, S, SO.sub.2, S--S, or NR;X is CH, C--OH or N;M is p-nitrophenylazo, 2,4-dinitrophenylazo, 2,4,6-trinitrophenylazo, p-nitrostyryl, p-benzoquinoneimino, bis-(4-dimethylaminophenyl) hydroxymethyl, 3-phenylisothiazolyl-5-azo, thiazolyl-5-azo, or isothiazolyl-5-azo;k is 1;l is 0 or 1; andn is 0 or 1.Type: GrantFiled: February 27, 1992Date of Patent: November 16, 1993Assignee: Miles Inc.Inventors: Eddy Chapoteau, Bronislaw P. Czech, Wolodymyr I. Zazulak
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Patent number: 5081233Abstract: 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: GrantFiled: October 24, 1988Date of Patent: January 14, 1992Assignee: Ricoh Company, Ltd.Inventors: Masaomi Sasaki, Tomoyuki Shimada
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Patent number: 5041539Abstract: The invention relates to a process for the preparation of concentrated storage-stable aqueous solutions of yellow azo- and azoxystilbene dyes which are obtained by self-condensation of 4-nitrotoluene-2-sulfonic acid in the presence of an alkali metal hydroxide, by converting the sparingly soluble alkali metal salt of the dye into a water-soluble ammonium salt by double cation exchange via a lipophilic ammonium salt, which process comprises carrying out the double ion exchange in a two-phase system of nitrobenzene/water and using, for the first ion exchange a di- or trialkylamine containing a total of 12 to 40 carbon atoms and, for the second ion exchange, a mono-, di- or trialkanolamine containing 2 to 4 carbon atoms in each alkyl moiety.The concentrated storage-stable dye solutions so obtained are particularly suitable for dyeing paper.Type: GrantFiled: June 19, 1989Date of Patent: August 20, 1991Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Paul Herzig, Jurgen Markert
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Patent number: 4954133Abstract: Compounds of the formula ##STR1## wherein each A, independently, is a ##STR2## wherein R.sub.1 is hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,R.sub.2 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, --NHCONH.sub.2 or --NHCOC.sub.1-4 alkyl,R.sub.3 is hydrogen or methoxy, andm is 0, 1 or 2,each B, independently, is a radical of a diazo or coupling component, and a and each b, independently, are 0 or 1,and metal complexes thereof, which compounds or complexes are in free acid or salt form, and mixtures thereof with a compound of the formula ##STR3## or a metal complex thereof, wherein A and b are as defined above and D is a radical of a diazo or coupling component of the benzene or 1-naphthalene series are useful for dyeing and printing hydroxy group- or nitrogen-containing organic substrates, especially cellulose fibre-containing textiles (e.g., cotton), paper and leather.Type: GrantFiled: February 12, 1986Date of Patent: September 4, 1990Assignee: Sandoz Ltd.Inventor: Max Oppliger
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Patent number: 4940783Abstract: Disazo dyes which are suitable for dyeing and printing, especially of paper of all kinds. The dyes correspond to the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each an alkyl radical,A is an alkylene radical,X and Y are nonionic substituents customarily in azo dyes andAn.sup..crclbar. is an anion.Type: GrantFiled: August 30, 1988Date of Patent: July 10, 1990Assignee: Ciba-Geigy CorporationInventor: Willy Stingelin
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Patent number: 4918169Abstract: Reactive dyes suitable for dyeing and printing cellulosic fiber materials by the cold pad-batch process having the formula ##STR1## wherein Fa is a monoazo or polyazo, metal complex azo, anthraquinone, phthalocyanine, formazane, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, napthoquinone, pyrenequinone or perylene-tetracarbimide dye radical, X is halogen, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl, a sulfonic acid or phosphonic acid group or a quaternized ammonium group, r is 1 or 2, R is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy or phenyl, and A is a radical of the formula ##STR2## wherein R' is hydrogen, C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy or phenyl, C.sub.5 -C.sub.Type: GrantFiled: August 19, 1988Date of Patent: April 17, 1990Assignee: Ciba-Geigy CorporationInventor: Karl Hoegerle
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Patent number: 4885254Abstract: A method for determining the extent of polymerization of a polymer system consisting of adding a fluorescent label, the label having a reactivity similar to the reactivity of the curing agent, to the polymer system and measuring the fluorescence intensity proportional to cure species concentration during polymerization. The fluorescence intensity of the label exhibits sensitive changes throughout the polymerization process, allowing one to follow cure reactions in a quantitive way by measuring fluorescence, especially in the latter stages of cure. The cure species composition, reactivity ratio, activation energy and weight-average molecular weight can also be determined by adding a label and measuring the UV-VIS spectra in addition to the fluorescence intensity.Type: GrantFiled: December 11, 1987Date of Patent: December 5, 1989Assignee: University of ConnecticutInventor: Chong S. P. Sung
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Patent number: 4791211Abstract: An improved process for the production of 2-stilbylnaphthotriazole optical bleaches which involves diazotizing aminostilbene 2-sulfonic acids, coupling the thus formed diazonium salt with naphthylamino-sulfonic acid to form the stilbylnaphthyl monoazo salt by adding the naphthylamino-sulfonic acid to the diazonium salt from the diazotization, neutralized to a pH in the range of 6-8, in the presence of 2-butoxyethanol, oxidizing said monoazo salt to form the 2-stilbylnaphthotriazole compounds with air in an aqueous alkaline medium containing butoxyethanol and isolating and recovering said 2-stilbylnaphotriazole optical bleaches as their sodium salts.Type: GrantFiled: January 20, 1987Date of Patent: December 13, 1988Assignee: Ciba-Geigy CorporationInventors: Richard B. Lund, Larry W. Bass
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Patent number: 4758659Abstract: A hexakisazo dye suitable for dyeing cellulose, natural or synthetic polyamide meterials, leather, represented by the formula ##STR1## wherein X is --CH.dbd.CH--, --CONH--, --CRH-- (wherein R is phenyl which is unsubstituted or substituted by H or a sulfonic acid group), -SO.sub.2 -- or --O--; Y is H, CH.sub.3 OCH.sub.3, Cl or SO.sub.3 M; A.sub.1 and A.sub.2 are each ##STR2## (wherein Z.sub.1 is H, Cl, CH.sub.3, OH, OCH.sub.3, OC.sub.2 H.sub.5 or SO.sub.3 M, and Z.sub.2 is H, CH.sub.3, NO.sub.2 or COOM); B.sub.1 and B.sub.2 are each ##STR3## (wherein Z.sub.3 is H, OH, NH.sub.2 Cl or COOM, Z.sub.4 is H, Cl, CH.sub.3, OH OCH.sub.3, NH.sub.2, COOM or SO.sub.3 M, and Z.sub.5 is H, C.sub.1 -C.sub.4 alkyl or OH); M is H, Na, K, Li or NH.sub.4 ; f is 0 or 1; m is 0, 1 or 2; and n is 0, 1 or 2.Type: GrantFiled: July 29, 1986Date of Patent: July 19, 1988Assignee: Orient Chemical Industries, Ltd.Inventors: Hisashi Senshu, Sadahiko Matsubara, Tamotsu Naito
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Patent number: 4743523Abstract: A photosensitive member for electrophotography comprising a photosensitive layer containing an azo pigment selected from those represented by the following formulas (1)-(6): ##STR1## wherein R is an alkyl, aralkyl, aryl, or acyl each capable of having a substituent; Ar is an arylene or heterocyclic group each capable of having a substituent; Ar is a coupler residue group having a phenolic OH group; B is hydrogen, nitroso, or an alkyl, aralkyl, aryl or acyl group capable of having a substituent; and n is 0 or 1.Type: GrantFiled: March 27, 1986Date of Patent: May 10, 1988Assignee: Canon Kabushiki KaishaInventors: Masataka Yamashita, Takao Takiguchi, Shoji Umehara, Masakazu Matsumoto, Shozo Ishikawa
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Patent number: 4742162Abstract: Condensates of an azo compound of the formula ##STR1## wherein n is 1 or 2, with the stilbene compound of the formula ##STR2## in the molar ratio of 1:1 to 2:1, dye leather in a yellowish-brown shade, which penetrate deeply into the leather, and give fast dyeings.Type: GrantFiled: April 6, 1984Date of Patent: May 3, 1988Assignee: Ciba-Geigy CorporationInventor: Ulrich Schlesinger
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Patent number: 4735882Abstract: An electrophotographic photosensitive member comprises a photosensitive layer containing an azo pigment selected from the following general formulae (1) to (5): ##STR1## wherein groups Ar are arylene groups and divalent heterocyclic groups, each of which may contain a substituent; n is 0 or 1; and group A is a coupler residue group having a phenolic OH group.Type: GrantFiled: April 1, 1986Date of Patent: April 5, 1988Assignee: Canon Kabushiki KaishaInventors: Masataka Yamashita, Takao Takiguchi, Shoji Umehara, Masakazu Matsumoto, Shozo Ishikawa
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Patent number: 4717674Abstract: A method for determining the extent of polymerization of an epoxy system consisting of adding a fluorescent label, the label having a reactivity similar to the reactivity of the curing agent, to the epoxy system and measuring the fluorescence intensity during polymerization. The fluorescence intensity of the label at its emission maximum increases sharply with polymerization, allowing one to follow cure reactions in a quantitative way by measuring fluorescence, especially in the later stages of cure beyond gelation. The composition, reactivity ratio, activation energy and weight-average molecular weight can also be determined by adding a label, such as p,p'-diaminoazobenzene (DAA) or trans diamine-stilbene (DAS), to mimic the reactivity of the curing agent, such as diaminodiphenyl sulfone (DDS) or methylene dianiline (MDA), and measuring the UV-VIS spectra in addition to the fluorescence intensity.Type: GrantFiled: June 25, 1986Date of Patent: January 5, 1988Inventor: Chong S. P. Sung
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Patent number: 4663442Abstract: 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: GrantFiled: July 18, 1985Date of Patent: May 5, 1987Assignee: Ricoh Co., Ltd.Inventor: Masafumi Ohta
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Patent number: 4650859Abstract: Chrome azo-azomethine dyes are disclosed which contain a benzthiazolylphenyl or stilbenyl radical bound via an aldehyde group to the aldehyde moiety of the azomethine dyes. The dyes are particularly useful for dyeing wool, polyamide and leather.Type: GrantFiled: December 31, 1984Date of Patent: March 17, 1987Assignee: Ciba-Geigy CorporationInventor: Fabio Beffa