Containing -c(=x)-, Wherein X Is Chalcogen (e.g., Carbonyl, Etc.) Patents (Class 534/829)
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Patent number: 5698682Abstract: The present invention provides a polarizing film having high heat resistance and a high degree of polarization and excellent optical properties by dyeing a polymer film with a novel azo compound represented by the following formula (1) or (2): ##STR1##Type: GrantFiled: February 18, 1997Date of Patent: December 16, 1997Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Yoriaki Matsuzaki, Ryu Oi, Rihoko Imai, Keisuke Takuma, Hisato Itoh
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Patent number: 5696243Abstract: Diphenylamines of the formula ##STR1## where the ring A can be benzo-fused, andD is aryl or a five-membered aromatic heterocyclyl which contains one to three hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, in the heterocyclic ring and can be fused to a benzene, thiophene, pyridine or pyrimidine ring,X is N.dbd.N or, if D is aryl, is alternatively CH.dbd.CH, or D--X together is 1,2,2-tricyanovinyl,R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy or halogen,R.sup.5 is prop-1-en-3-yl, acryloyl or methacryloyl,R.sup.6 and R.sup.7 are each hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, halogen, prop-1-en-3-yl, acryloyl, methacryloyl or oxiranylmethoxy, andY is C.sub.1 -C.sub.20 -alkylene,polymers derived from the compounds, and their use in non-linear optics.Type: GrantFiled: April 19, 1996Date of Patent: December 9, 1997Assignee: GASF AktiengesellschaftInventors: Stefan Beckmann, Karl-Heinz Etzbach, Ruediger Sens
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Patent number: 5691459Abstract: Azo dyes of the formula ##STR1## in which R.sub.1 and R.sub.2 independently of one another are unsubstituted or hydroxy-, C.sub.1 -C4-alkoxy- or halogen-substituted C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy;unsubstituted or C.sub.1 -C4-alkyl-, C.sub.1 -C4-alkoxy- or halogen-substituted phenyl or phenoxy; ora radical of the formula --N(R.sub.3)R.sub.4, in which R.sub.3 und R.sub.4 independently of one another are hydrogen, C.sub.1 -C.sub.4 -alkyl, or C.sub.2 -C.sub.4 -alkanoyl which is unsubstituted or further substituted in the alkyl part by hydroxyl or C.sub.1 -C.sub.4 -alkoxy,with the proviso that R.sub.1 and R.sub.2 are not simultaneously methyl, produce dyeings with good fastnesses on fibre materials containing nitrogen or containing hydroxyl groups.Type: GrantFiled: July 15, 1996Date of Patent: November 25, 1997Assignee: Ciba-Geigy CorporationInventors: Jean-Marie Adam, Peter Sutter
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Patent number: 5684139Abstract: Dyestuffs of the formula (I) ##STR1## wherein R.sup.1 and R.sup.4 independently of one another represent an acyl radical,R.sup.2 and R.sup.3 independently of one another represent hydrogen or unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl,X represents a bridge member which is not fibre-reactive andn and m independently of one another represent 1 or 2,are outstandingly suitable for dyeing and printing substrates containing hydroxyl and/or amide groups, in particular for printing paper by the ink-jet method.Type: GrantFiled: July 5, 1996Date of Patent: November 4, 1997Assignee: Bayer AktiengesellschaftInventors: Peter Wild, Karin Hassenruck, Frank-Michael Stohr
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Patent number: 5650497Abstract: Azo dyes of the formula ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 independently of one another are hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen,R.sub.6 is hydrogen or C.sub.1 -C.sub.4 Alkyl,X is --C.sub.1 -C.sub.4 alkylene-O--C.sub.1 -C.sub.4 alkyl andY is hydrogen; unsubstituted or hydroxy- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.4 -alkonoyl or C.sub.1 -C.sub.4 alkoxycarbonyl; a radical of the formula --CH.sub.2 --CH.dbd.CH.sub.2 ;C.sub.1 -C.sub.4 alkylsulfonyl; or unsubstituted or C.sub.1 -C.sub.4 alkyl-, C.sub.1 -C.sub.4 alkoxy- or halogen-substituted phenylsulfonyl, produce dyeings with good fastness properties on fibre materials containing nitrogen or containing hydroxyl groups.Type: GrantFiled: July 15, 1996Date of Patent: July 22, 1997Assignee: Ciba-Geigy CorporationInventors: Jean-Marie Adam, Peter Sutter
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Patent number: 5580965Abstract: Disazo dyestuffs have been found which, in the form of the free acid, correspond to the formula (I) ##STR1## represents H or an optionally substituted aliphatic or aromatic radical and R.sup.1 to R.sup.6 and A have the meaning given in the description, which are outstandingly suitable for inkjet printing.Type: GrantFiled: March 20, 1996Date of Patent: December 3, 1996Assignee: Bayer AktiengesellschaftInventor: Horst J ager
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Patent number: 5571898Abstract: There are described dyes of the formula ##STR1## where the ring A may be benzofused, R.sup.1 is substituted or unsubstituted C.sub.1 -C.sub.13 -alkyl, substituted or unsubstituted phenyl, C.sub.1 -C.sub.8 -alkanoyl, substituted or unsubstituted benzoyl, substituted C.sub.2 -C.sub.4 -alkanoyl, or substituted diaminotriazinyl,R.sup.2 is hydrogen or C.sub.1 -C.sub.4 -alkyl or R.sup.1 and R.sup.2 together with the nitrogen atom joining them together are a heterocyclic radical,R.sup.3 and R.sup.4 are each substituted or unsubstituted C.sub.1 -C.sub.13 -alkyl, substituted or unsubstituted C.sub.5 -C.sub.7 -cycloalkyl or substituted or unsubstituted piperidinyl and R.sup.3 may also be hydrogen,R.sup.5 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.2 -C.sub.5 -alkanoylamino, halogen, nitro, cyano, substituted or unsubstituted phenylazo, C.sub.2 -C.sub.4 -alkanoylamino substituted by a quaternizable or quaternary group, or C.sub.2 -C.sub.4 -alkoxy, C.sub.2 -C.sub.4 -alkoxycarbonyl or C.sub.2 -C.Type: GrantFiled: July 11, 1995Date of Patent: November 5, 1996Assignee: BASF AktiengesellschaftInventors: Ulrike Schloesser, Udo Mayer
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Patent number: 5554738Abstract: Anionic disazo dyes useful for dyeing and printing textile materials, paper and leather and for the preparation of inks of the formula ##STR1## wherein D, R.sup.3, R.sup.4, M, R.sup.5 and R.sup.7 are defined as in the specification.Type: GrantFiled: October 18, 1991Date of Patent: September 10, 1996Assignee: Ciba-Geigy CorporationInventors: Jean-Marie Adam, Adolf K aser
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Patent number: 5549853Abstract: Azo dyes of the formulaW(--X--Y--Chr).sub.n,wheren is 2 to 6,y is C.sub.1 -C.sub.6 -alkylene,Chr is the radical of a mono- or polyazo dye,X is a radical of the formula CO--O or O--CO andW is an n-valent radical which is derived from an unsubstituted or substituted C.sub.2 -C.sub.20 -alkane, an unsubstituted or substituted C.sub.4 -C.sub.7 -cycloalkane, an unsubstituted or substituted benzene or an unsubstituted or substituted naphthalene, or, if n is 4, is also silicon,and their use in nonlinear optics or for dyeing or printing textile materials are described.Type: GrantFiled: June 6, 1994Date of Patent: August 27, 1996Assignee: BASF AktiengesellschaftInventors: Stefan Beckmann, Karl-Heinz Etzbach, Karl Siemensmeyer, Ruediger Sens
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Patent number: 5527889Abstract: Azo dyes of formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, unsubstituted C.sub.2 -C.sub.4 alkanoylamino or C.sub.2 -C.sub.4 alkanoylamino which is substituted by hydroxy, sulfo or sulfato, or are halogen or sulfo,R.sub.3, R.sub.4 and R.sub.5 are each independently of one another hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen or sulfo,R.sub.6 is hydrogen, C.sub.1 -C.sub.4 alkyl, halogen, sulfo, unsubstituted C.sub.2 -C.sub.4 alkanoylamino or C.sub.2 -C.sub.4 alkanoylamino which is substituted by hydroxy, sulfo or sulfato, or is a radical of formula --O--Y, wherein Y is hydrogen, C.sub.1 -C.sub.8 alkyl or C.sub.1 -C.sub.8 alkyl which is substituted by hydroxy, C.sub.1 -C.sub.4 alkoxy, sulfo or sulfato,R.sub.7 is hydrogen, C.sub.1 -C.sub.8 alkyl or hydroxy-substituted C.sub.1 -C.sub.8 alkyl, or C.sub.2 -C.sub.8 alkyl which is interrupted in the chain by the group --O-- or ##STR2## and X is C.sub.1 -C.Type: GrantFiled: April 17, 1995Date of Patent: June 18, 1996Assignee: Ciba-Geigy CorporationInventors: Jurgen Schaetzer, James C. Posey
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Patent number: 5420258Abstract: Azo dyes of formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, X, Y and n are as defined in claim 1, give dyeings of good fastness properties on nitrogen-containing or hydroxyl group containing fibre materials.Type: GrantFiled: August 23, 1993Date of Patent: May 30, 1995Assignee: Ciba-Geigy CorporationInventors: Jurgen Schaetzer, James C. Posey
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Patent number: 5312906Abstract: 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: GrantFiled: July 24, 1992Date of Patent: May 17, 1994Assignee: Ricoh Company, Ltd.Inventor: Masakatsu Shimoda
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Patent number: 5298036Abstract: Azo dyes of the formula ##STR1## in which R.sub.1 and K are as defined in claim 1, produce on nitrogen-containing or hydroxyl-containing fibre materials dyeings having good fastness properties.Type: GrantFiled: July 14, 1992Date of Patent: March 29, 1994Assignee: Ciba-Geigy CorporationInventors: Dieter Mausezahl, Urs Lehmann
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Patent number: 5281263Abstract: According to the present invention there is provided a compound which, in the free acid form, is of the Formula (1): ##STR1## wherein A is an optionally substituted phenyl or naphthyl group;Z is H, CO.sub.2 H, SO.sub.3 H or SO.sub.2 NH.sub.2 ;T is H or SO.sub.3 H;R.sup.1 is H or optionally substituted alkyl;V is H, CO.sub.2 H, SO.sub.3 H, CH.sub.3 or Cl; provided that the compound of Formula (1) has at least as many CO.sub.2 H groups as SO.sub.3 H groups.The compound is useful as a colorant for inks used in ink jet printing.Type: GrantFiled: January 21, 1992Date of Patent: January 25, 1994Assignee: Imperial Chemical Industries PLCInventors: Peter Gregory, Prahalad M. Mistry
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Patent number: 5278293Abstract: Azo dyestuffs of the formula ##STR1## having the substituent meanings given in the description, are outstandingly suitable for dyeing and printing materials containing hydroxyl groups and amide groups.Type: GrantFiled: October 31, 1990Date of Patent: January 11, 1994Assignee: Bayer AktiengesellschaftInventors: Karl-Josef Herd, Manfred Hoppe, Hermann Henk, Klaus Kunde, Frank-Michael Stuohr
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Patent number: 5262527Abstract: Anionic azo compounds which, in the free acid form, have the Formula (1): ##STR1## Ar.sup.1 and Ar.sup.2 are each independently aryl or substituted aryl providing at least one of Ar.sup.1 and Ar.sup.2 has at least one substituent selected from COOH and COSH;each R.sup.1 and R.sup.2 is independently H, alkyl, substituted alkyl, alkenyl or substituted alkenyl;L is a divalent organic linking group;n is 0 or 1;each X independently is carbonyl or a group of the formula (2), (3) or (4): ##STR2## each Z independently is NR.sup.3 R.sup.4, SR.sup.5 or OR.sup.5 ; each Y independently is H, Cl, Z, SR.sup.6 or OR.sup.6 ;each E independently is Cl or CN;R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl, substituted aryl, aralkyl, substituted aralkyl or R.sup.3 and R.sup.Type: GrantFiled: June 28, 1991Date of Patent: November 16, 1993Assignee: Imperial Chemical Industries PLCInventors: Peter Gregory, Ronald W. Kenyon, Prahalad M. Mistry
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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: 5258505Abstract: Disclosed herein is an azo compound represented by the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 each are a group or atom selected from the group consisting of a hydrogen atom, alkyl groups having 1 to 4 carbon atoms, a methoxy group, halogen atoms, COOM and COOR.sub.4 in which R.sub.4 is an alkyl group having 1 to 4 carbon atoms, and M denotes an alkali metal atom, or an ammonium or organic ammonium ion. An ink containing this compound is suitable for use in an ink-jet recording.Type: GrantFiled: March 27, 1992Date of Patent: November 2, 1993Assignee: Canon Kabushiki KaishaInventors: Tsuyoshi Eida, Mayumi Yamamoto, Takao Yamamoto
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Patent number: 5254675Abstract: A compound which, in the free acid form, is of the Formula (1): ##STR1## wherein B is 3- or 4-carboxyphenyl; andX is H.The compound is useful in the preparation of inks for ink jet printing of substrates such as paper, on which it gives highly water fast prints which show little bronzing.Type: GrantFiled: January 3, 1992Date of Patent: October 19, 1993Assignee: Imperial Chemical Industries PLCInventors: Peter Gregory, Prahalad M. Mistry, David Greenwood
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Patent number: 5243033Abstract: Reactive dyes of the formula ##STR1## in which R.sub.1, R.sub.2 and R.sub.3, independently of one another, are C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, ureido, C.sub.1 -C.sub.4 acylamino, carboxyl and sulfo and n, m and p, independently of one another, are the number 0, 1, 2 or 3, X is fluorine or chorine and Z is an aliphatic, araliphatic, aromatic or heterocyclic amino group free from fibre-reactive radicals; or Z is the radical of an aliphatic or aromatic diamine which contains the radical of the formula ##STR2## in which R.sub.1, R.sub.2, R.sub.3, n, m, p and X are as defined, bound via the second amino group; or Z is a radical of the formula ##STR3## in which R.sub.1, R.sub.2, R.sub.3, n, m, and p are as defined; or Z is a radical --NH--SO.sub.2 --(CH.sub.2).sub.2 --OSO.sub.3 H; and the reactive dye of the formula (1) contains at least two sulfo groups, produce, on cellulose fibres, orange dyeings of high color strength and prints of good fastness properties.Type: GrantFiled: January 13, 1992Date of Patent: September 7, 1993Assignee: Ciba-Geigy CorporationInventor: Athanassios Tzikas
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Patent number: 5225545Abstract: The compounds of the formula (1) indicated in claim 1 are suitable for use as direct dyes for dyeing and printing a wide range of materials, in particular cellulose-containing fibre materials, producing dyeings and prints having good fastness properties.Type: GrantFiled: May 12, 1992Date of Patent: July 6, 1993Assignee: Ciba-Geigy CorporationInventor: Urs Lauk
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Patent number: 5198022Abstract: A alkali-soluble dye for a waterfast ink having structural formula as follows: ##STR1## and an ink containing the dye dissolved in water. Printing from the ink is insoluble below pH 6.0; is an intense black at low concentration; and remains black on acid papers. The aqueous inks are stable and exhibit good printhead nozzle maintenance.Type: GrantFiled: January 17, 1992Date of Patent: March 30, 1993Assignee: Lexmark International, Inc.Inventors: Rodney O. Aulick, Bradley L. Beach, Donald L. Elbert, Terence E. Franey, James F. Feeman, John M. Olson, Allen C. Sanders, Robert L. Vollmer
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Patent number: 5185435Abstract: The present invention relates to the preparation of bisazo pigments by reaction (a) of 2 mol of an azocarbonyl chloride of the formula ##STR1## with 1 mol of a diamine of the formula ##STR2## by reaction (b) of one mole of a bis(azocarbonyl chloride) of the formula ##STR3## with 2 mol of an amine of the formula ##STR4## which comprises carrying out the reactions (a) or (b) in the presence of 1,2,3-trimethylbenzene or anisole as the solvent.Type: GrantFiled: January 30, 1992Date of Patent: February 9, 1993Assignee: Ciba-Geigy CorporationInventors: Klaus Ruf, Bilge Gulec, Michael Reisinger, Werner Surber
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Patent number: 5177195Abstract: A compound which, in the free acid form, is of the Formula (1): ##STR1## wherein B is 3,4- or 3,5-dicarboxyphenyl.The compound is useful in the preparation of inks for ink jet printing of paper, on which it has high water-fastness and low bronzing.Type: GrantFiled: January 3, 1992Date of Patent: January 5, 1993Assignee: Imperial Chemical Industries PLCInventors: Peter Gregory, Prahalad M. Mistry
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Patent number: 5175258Abstract: A process for the preparation of photogenerating pigments which comprises the reaction of a diaminofluorenone with an alkali nitrite, an acid, and a tetrafluoroborate; thereafter reacting the resulting product with an anilide coupler; and subsequently annealing the product obtained.Type: GrantFiled: December 14, 1990Date of Patent: December 29, 1992Assignee: Xerox CorporationInventors: Kock-Yee Law, Ihor W. Tarnawskyj
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Patent number: 5149366Abstract: A disazo compound of the formula (I) in the free acid form, ##STR1## and an ink jet recording ink composition containing the same are provided, and the composition is superior in stability during storage or use, heat resistance, image clearness, water resistance and light fastness, and has a desirable tint as a red color.Type: GrantFiled: October 9, 1991Date of Patent: September 22, 1992Assignees: Sumitomo Chemical Company, Limited, Taoka Chemical CompanyInventors: Hideo Kawashita, Mituhiro Ohta, Kazuya Ogino
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Patent number: 5145953Abstract: A biscyclobutarene monomer is prepared having two cyclobutarene moieties bridged by a divalent radical having at least one azo linkage. The monomers can be polymerized to form polymers exhibiting outstanding thermooxidative stability at high temperatures for prolonged time periods.Type: GrantFiled: February 2, 1988Date of Patent: September 8, 1992Assignee: The Dow Chemical CompanyInventors: Robert A. Kirchhoff, Alan K. Schrock
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Patent number: 5075429Abstract: A monoazo compound of the formula, ##STR1## wherein D is a heterocyclic or carbocyclic compound residue such as benzothiazolyl and phenyl, X is hydrogen, alkyl, alkoxy, halogeno, acylamino or the like, Y is hydrogen, halogeno, alkyl, alkoxy and the like, R.sub.1 is alkyl, R.sub.2 is C.sub.2 -C.sub.4 alkylene, B is a bridging group such as ##STR2## --O--, --S--, C.sub.1 -C.sub.6 alkylene and the like, and W.sub.1, W.sub.2, W.sub.3, Z.sub.1, Z.sub.2 and Z.sub.3 are independently hydrogen, alkyl, halogeno or the like, which is useful for dyeing hydrophobic fiber materials to give dyed or printed product of a deep color excellent in fastness properties, particularly those such as washing fastness, even after various finishing treatments of the product.Type: GrantFiled: October 10, 1989Date of Patent: December 24, 1991Assignee: Sumitomo Chemical Company LimitedInventors: Jun Yamamoto, Yasuyoshi Ueda, Takashi Omura, Yosuke Yamamoto, Hideo Hattori, Junichi Sekihachi
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Patent number: 5053495Abstract: A dye which, in the free acid form, has the formula ##STR1## wherein W is COOHX is selected from H, COOH, SO.sub.3 H, halo, hydroxy, nitro, cyano, C.sub.1-6 -alkyl, C.sub.1-6 -alkoxy and C.sub.1-6 -acylamino;Y is H, COOH or SO.sub.3 H;Z is H, COOH or SO.sub.3 H;R & R.sup.1 are each independently H or C.sub.1-6 -alkyl substituted by 0, 1 or 2 --COOR.sup.2 groups; andR.sup.2 is H or C.sub.1-6 -alkyl;provided that there are at least two COOH groups and that the number of COOH groups is equal to or greater than the number of SO.sub.3 H groups.The dye is adapted for the preparation of inks for use in ink jet printing in which it displays high water-fastness on paper.Type: GrantFiled: August 24, 1989Date of Patent: October 1, 1991Assignee: Imperial Chemical Industries PLCInventors: David Greenwood, Nigel Hughes, Ronald W. Kenyon, Suraj L. Hindagolla
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Patent number: 5037967Abstract: 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: GrantFiled: November 7, 1989Date of Patent: August 6, 1991Assignee: Ciba-Geigy CorporationInventors: Angelo D. Casa, Peter Liechti, Max Dempfle
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Patent number: 4994563Abstract: The azo dyes of the formula ##STR1## in which D is a diazo component, R.sub.1 and R.sub.2 independently of one another are each a C.sub.1 -C.sub.10 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or naphthyl radical each of which is substituted or unsubstituted, or R.sub.1 and R.sub.2, together with the nitrogen atom linking them, are a 5-membered, 6-membered or 7-membered ring each of which is unsubstituted or substituted by heteroatoms, R.sub.3 is hydrogen, halogen or a C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxy or phenoxy radical each of which is substituted or unsubstituted, X is --CO-- or --SO.sub.2 --, n is the number 1, 2, 3, 4, 5 or 6 and M is a cation, produce dyeings of good fastness properties on fibre materials containing nitrogen or containing hydroxyl groups. This application also relates to the preparation and use of said azo dyes and to intermediates utilized in the preparation of said azo dyes.Type: GrantFiled: June 27, 1989Date of Patent: February 19, 1991Assignee: Ciba-Geigy CorporationInventors: Harald Walter, Rudolf Hurter
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Patent number: 4988805Abstract: The dyestuffs of the general formulae ##STR1## and salts thereof whereinX denotes hydrogen, alkoxy or NHR.sub.3,R denotes hydrogen, alkyl or alkoxy,R.sub.1 denotes alkyl,R.sub.2 and R.sub.3 denote hydrogen, alkyl, alkylcarbonyl, alkylsulphonyl, aryl, arylcar=bonyl, arylsulphonyl, aralkyl, aralkylcarbonyl or aminocarbonyl andm and n denote 1 or 2, andwherein the substituents mentioned can, in turn, be substituted by nonionic radicals or carboxylic or sulphonic acid groups customary in dyestuffs chemistry, are used for dyeing cellulose-containing materials and leather.Type: GrantFiled: July 14, 1988Date of Patent: January 29, 1991Assignee: Bayer AktiengesellschaftInventor: Klaus Kunde
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Patent number: 4978747Abstract: Colorants are obtained by reacting a dyestuff which is free from ionic groups and has.gtoreq.2 NH.sub.2 groups which are preferably arranged in such a manner that they do not participate in the resonance of the chromophore with such an amount of a (cyclo)aliphatic diisocyante so as to form an adduct that still contains at least two free NCO groups, and subsequently reacting this adduct with a (cyclo)aliphatic diamine, to form an adduct suitable for dyeing and pigmenting macromolecular substances, in particular for coloring PUR-based paints, coatings and laminates.Type: GrantFiled: April 13, 1989Date of Patent: December 18, 1990Assignee: Bayer AktiengesellschaftInventors: Karl-Arnold Weber, Hermann Henk, Klaus Kunde, Jochen Westphal, Klaus Wunderlich
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Patent number: 4965345Abstract: Solvent dyes of the formula ##STR1## where ##STR2## R.sup.1 and R.sup.2 are each, independently of the other, hydrogen, methyl, ethyl, methoxy or ethoxy,n is 0 or 1 andk, if n is 0, is the radical of a coupling component of the pyrazolone series or, if n is 1, is the radical of a coupling component of the pyrazolone, 2-naphthol, hydroxyquinoline, aniline, naphthylamine, pyridone or 2,6-diaminopyridine series,R.sup.3 and R.sup.4 each independently of the other being C.sub.1 -C.sub.22 -alkyl which may be substituted or interrupted by oxygen, imino or C.sub.1 -C.sub.4 -alkylimino, subject to the proviso that COR has more than 8 carbon atoms, are very highly suitable for coloring organic substrates.Type: GrantFiled: October 2, 1987Date of Patent: October 23, 1990Assignee: BASF AktiengesellschaftInventor: Hermann Loeffler
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Patent number: 4956457Abstract: The new azo compounds are represented by the following general formula I ##STR1## Wherein R and R.sup.1 are hydrogen, --COCR.sub.3.sup.4 --COCHR.sub.2.sup.4, --SO.sub.2 CH.sub.3, --CO.sub.2 C.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 R.sup.4, --( CH.sub.2 CH.sub.2 R.sup.4).sub.2, --CH.sub.2 CH.sub.2 OH, --CONHCH.sub.2 CH.sub.2 R.sup.4 or --CH.sub.2 CH.sub.2 OCONH.sub.2 and R.sup.4 is Cl or a group of the formula ##STR2## --NHCO.sub.2 CH.sub.3 CH.sub.2 OH, --NHCO.sub.2 C.sub.2 H.sub.5, --NHOH, --NHCONHOH, or --NHCH.sub.3, whereby R.sup.1 and R.sup.2 are similar or dissimilar.Type: GrantFiled: August 10, 1989Date of Patent: September 11, 1990Inventor: Takeo Takayanagi
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Patent number: 4910299Abstract: Disperse dyes suitable for dyeing textile material composed of polyester dyes of the formula ##STR1## in which D is the radical of a substituted or unsubstituted, homocyclic or heterocyclic diazo component belonging to the series comprising thienyl, thiazolyl, isothiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, benzothiazolyl, benzoisothiazolyl, pyrazolyl, imidazolyl or phenyl,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 ring or 6-membered ring,B is a l inear or branched C.sub.2 -C.sub.6 -alkylene radical,W is halogen, C.sub.Type: GrantFiled: December 2, 1987Date of Patent: March 20, 1990Assignee: Ciba-Geigy CorporationInventors: Angelo D. Casa, Peter Liechti, Max Dempfle
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Patent number: 4904765Abstract: Dye mixtures contain an oil-soluble dye and a dye of the formula ##STR1## where D is phenyl which is unsubstituted or substituted by methyl or methoxy, R is hydrogen or methyl, R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sup.2 is C.sub.3 - or C.sub.4 -alkyl.The mixtures according to the invention are preferably used for coloring and marking mineral oil products.Type: GrantFiled: July 14, 1987Date of Patent: February 27, 1990Assignee: BASF AktiengesellschaftInventors: Bernd Derber, Rudolf Denninger
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Patent number: 4863910Abstract: A complex of an azo compound of the formula ##STR1## wherein R and R' are selected from the group consisting of hydrogen, --COCR.sub.4.sup.3, --COCHR.sub.2.sup.4, --CO.sub.2 C.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 R.sup.4, --(CH.sub.2 CH.sub.2 R.sup.4)2, --CH.sub.2 CH.sub.2 OH, --CONHCH.sub.2 CH.sub.2 R.sup.4 and --CH.sub.2 CH.sub.2 OCOHN.sub.2, R.sup.4 is selected from the group consisting of chlorine, ##STR2## --NHCO.sub.2 CH.sub.2 CH.sub.2 OH, --HNCO.sub.2 C.sub.2 H.sub.5, --NHOH, --NHCONHOH and --NHCH.sub.3 ; R.sup.1 and R.sup.2 are individually selected from the group consisting of ##STR3## --NHCH.sub.2 CH.sub.2 Cl, --NHCONHOH, --NHCO.sub.2 C.sub.2 H.sub.5, 6-mercapropurin, 5-fluoruracil and prenissolin, R.sup.3 is selected from the group consisting of hydrogen, --COCHR.sub.2.sup.4, --SO.sub.2 CH.sub.3, --COC.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 R.sub.4 and --CONH.sub.2, R.sup.Type: GrantFiled: May 20, 1986Date of Patent: September 5, 1989Inventor: Takeo Takayanagi
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Patent number: 4861344Abstract: Water-soluble azo compounds having useful fiber-reactive dye properties conforming to the general formula ##STR1## in which: A is phenylene which may be substituted or unsubstituted, or is a radical of the formula ##STR2## in which W is a direct bond or a radical of the formula --CH.dbd.CH-- or --NH--CO--NH-- and R* denotes hydrogen, nitro, sulfo, carboxy, methyl, ethyl, methoxy or ethoxy;n is the number zero or 1;B is a radical of the formula ##STR3## where R is equal to carboxy or carbamoyl; M is hydrogen or an alkali metal; andK is one of five radicals described in the specification, each of which contains a fiber-reactive group.These azo compounds produce fast dyeings on carboxamido- and/or hydroxy-containing materials, in particular cellulose fibers. On cellulose, fast dyeings are also obtained in a weakly acid to neutral medium, for example together with disperse dyes for dyeing a polyester fiber portion.Type: GrantFiled: October 30, 1987Date of Patent: August 29, 1989Assignee: Hoechst AktiengesellschaftInventors: Ludwig Schlafer, Hartmut Springer, Reinhard Hahnle
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Patent number: 4841037Abstract: A naphthalene trisazo compound represented by the general formula (I) or (II): ##STR1## wherein A and B each represents a substituted or unsubstituted benzene or naphthalene ring; m represents zero or 1; and M represents an alkali metal atom, ammonium or H.Am (wherein Am represents an amine); or ##STR2## wherein X represents a hydrogen atom, a lower alkyl group, a phenyl group or a phenyl group substituted by --SO.sub.3 M; m represents zero or 1; M represents an alkali metal atom, ammonium or H.Am (wherein Am represents an amine); A, B and C each represents a substituted or an unsubstituted benzene or naphthalene ring, provided that B and C do not represent a naphthalene ring at the same time. A recording liquid containing these compounds is suitable for use in an ink-jet recording system.Type: GrantFiled: June 10, 1986Date of Patent: June 20, 1989Assignees: Canon Kabushiki Kaisha, Mitsubishi Chemical Industries LimitedInventors: Tokuya Ohta, Masatsune Kobayashi, Yuko Suga, Konoe Miura, Hiroshi Takimoto, Tomio Yoneyama
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Patent number: 4760003Abstract: An electrophotographic photosensitive member comprises a photosensitive layer on a substrate, said photosensitive layer comprising a disazo pigment represented by the formula (1).Type: GrantFiled: May 21, 1986Date of Patent: July 26, 1988Assignee: Canon Kabushiki KaishaInventors: Masakazu Matsumoto, Takao Takiguchi, Masataka Yamashita, Shoji Umehara, Shozo Ishikawa, Hajime Miyazaki
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Patent number: 4754020Abstract: A new method of diazotization consists in using as the diazotizing agent in an aqueous, aqueous organic or organic medium the system comprising salt of nitrous acid+acid insoluble in the reaction medium, in particular organic or inorganic cation exchangers having acid groups. The diazonium salt solutions thus prepared are immediately reacted with coupling components to give azo dyestuffs, the insoluble acid and/or its salt being separated off before or after the coupling.Type: GrantFiled: March 7, 1986Date of Patent: June 28, 1988Assignee: Bayer AktiengesellschaftInventors: Joachim Wolff, Karlheinz Wolf, Reinhold M. Klipper, Peter M. Lange
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Patent number: 4752337Abstract: Recording liquid for ink jet recording systems containing dyestuffs of the formulae ##STR1## with the substituent definitions given in the description. They form high-contrast images of high fastness to water, light and abrasion.Type: GrantFiled: June 5, 1987Date of Patent: June 21, 1988Assignee: Bayer AktiengesellschaftInventor: Klaus Kunde
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Patent number: 4734218Abstract: Provided are novel dichroic azo dyestuffs, which contain skeletons represented by the following general formula: ##STR1## at one terminals of the long axes of the molecules of the azo dyestuffs, and liquid crystal compositions containing the dichroic azo dyestuffs in forms dissolved in liquid crystals. These dichroic azo dyestuffs have large dichroic ratios and high durability, and their compositions are employed as useful display devices.Type: GrantFiled: July 18, 1986Date of Patent: March 29, 1988Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Keisuke Takuma, Kimitoshi Kato, Hiroshi Aiga, Yasuyuki Yamada, Tsutomu Nishizawa
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Patent number: 4703113Abstract: A water-soluble dye, free from cellulose reactive groups, of the formula: ##STR1## wherein R.sup.1 is --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H,R.sup.2 is H or --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H, orR.sup.1 & R.sup.2 together with the nitrogen atom form a morpholine ringa & b are different and from 1 to 8m is from 1 to 10;n is from 0 to 9;M is H, ammonium, or a monovalent metal;X (i) NR.sup.1 R.sup.2, (ii) NR.sup.3 R.sup.4, in which R.sup.3 and R.sup.Type: GrantFiled: August 12, 1985Date of Patent: October 27, 1987Assignee: Imperial Chemical Industries PLCInventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
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Patent number: 4694075Abstract: The compounds of the formula ##STR1## where Y is hydrogen, chlorine, bromine or nitro, Z is hydrogen, chlorine, bromine, a sulfonic ester group or unsubstituted or substituted sulfamyl, X is --O-- or ##STR2## R is alkylene which may or may not be interrupted by oxygen or ##STR3## m is 0 or 1, p is 1 or 2, R.sup.1 and R.sup.2 independently of one another are each hydrogen, unsubstituted or substituted alkyl, alkenyl, cycloalkyl, aralkyl, or aryl, or R.sup.1 and R.sup.2 together with the nitrogen form a heterocyclic structure, R.sup.3 is hydrogen or unsubstituted or substituted alkyl, R.sup.6 and R.sup.7 independently of one another are each hydrogen, unsubstituted or substituted alkyl, alkoxy or acylamino, K is a radical of a coupling component, A.crclbar. is an anion, R.sup.4 is unsubtituted or substituted alkyl and R.sup.5 is hydrogen or C.sub.1 -C.sub.Type: GrantFiled: January 21, 1986Date of Patent: September 15, 1987Assignee: BASF AktiengesellschaftInventors: Horst Colberg, Erwin Hahn
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Patent number: 4676923Abstract: New dichroic dyestuffs for the guest-host type liquid crystal and new liquid crystal compositions containing said dyestuff having an excellent improved dichroism and being prepared by introducing at least one group selected from the group consisting of phenyl, cyclohexyl, phenylcarbonyloxy and phenyloxycarbonyl group into a phenyl, a cyclohexyl or a naphthyl group at its 4-position, which is arranged at the end of a known dichroic dyestuff molecule along the major axis of the molecule.Type: GrantFiled: December 2, 1985Date of Patent: June 30, 1987Assignee: Kabushiki Kaisha Nippon Kanko Shikiso KenkyushoInventors: Shigeo Yasui, Masashi Ono, Seiko Kobayashi, Shigeo Senzai, Tatsuo Uchida
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Patent number: 4663440Abstract: A brown reactive dye represented by a free acid of the formula, ##STR1## wherein R is a hydrogen atom or a C.sub.1 to C.sub.4 alkyl group, X is --SO.sub.2 CH.sub.2 CH.sub.2 Cl, --SO.sub.2 CH.dbd.CH.sub.2, --SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H or --SO.sub.2 CH.sub.2 CH.sub.2 OPO.sub.3 H.sub.2, rings A, B and C are each a benzene or naphthalene ring which may have other substituent, m is 0 to 3 and n is 0 to 1.This dye is suitable for dyeing cellulose fibers brown to afford dyeings superior in fastnesses, acid stability, build-up property and level dyeing property.Type: GrantFiled: May 26, 1981Date of Patent: May 5, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Takashi Omura, Masaki Sunami, Yasuo Tezuka
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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: 4645832Abstract: Reactive azo dyes represented by the general formula (I) or (II): ##STR1## wherein M is a hydrogen atom or an alkali metal, R.sup.1 is a hydrogen atom, a chlorine atom, a lower alkyl group, a lower alkoxy group, a nitro group or a carboxyl group, R.sup.2 and R.sup.8 are a lower alkyl group, a lower alkoxy group or a sulfonic acid group, R.sup.3, R.sup.7 and R.sup.9 are a hydrogen atom, a lower alkyl group, a lower alkoxy group, an acetylamino group or a sulfonic acid group, R.sup.4 and R.sup.5 are a hydrogen atom, a methyl group, a methoxy group or a sulfonic acid group, R.sup.6 is a hydrogen atom, a lower alkyl group, a lower alkoxy group or a sulfonic acid group, Z.sup.1 is a chlorine atom, a fluorine atom, an aliphatic or an aromatic amino residual group, a methoxy group or a phenoxy group, Z.sup.2 is the same one as Z.sup.1 when Z.sup.3 is ##STR2## Z.sup.2 is a chlorine atom or a fluorine atom when Z.sup.Type: GrantFiled: April 9, 1985Date of Patent: February 24, 1987Assignee: Mitsubishi Chemical Industries LimitedInventors: Toshio Niwa, Yoshiaki Kato