Containing -c(=x)-, Wherein X Is Chalcogen (e.g., Carbonyl, Etc.) Patents (Class 534/829)
  • Patent number: 5698682
    Abstract: 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: Grant
    Filed: February 18, 1997
    Date of Patent: December 16, 1997
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Yoriaki Matsuzaki, Ryu Oi, Rihoko Imai, Keisuke Takuma, Hisato Itoh
  • Patent number: 5696243
    Abstract: 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: Grant
    Filed: April 19, 1996
    Date of Patent: December 9, 1997
    Assignee: GASF Aktiengesellschaft
    Inventors: Stefan Beckmann, Karl-Heinz Etzbach, Ruediger Sens
  • Patent number: 5691459
    Abstract: 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: Grant
    Filed: July 15, 1996
    Date of Patent: November 25, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Jean-Marie Adam, Peter Sutter
  • Patent number: 5684139
    Abstract: 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: Grant
    Filed: July 5, 1996
    Date of Patent: November 4, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Wild, Karin Hassenruck, Frank-Michael Stohr
  • Patent number: 5650497
    Abstract: 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: Grant
    Filed: July 15, 1996
    Date of Patent: July 22, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Jean-Marie Adam, Peter Sutter
  • Patent number: 5580965
    Abstract: 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: Grant
    Filed: March 20, 1996
    Date of Patent: December 3, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventor: Horst J ager
  • Patent number: 5571898
    Abstract: 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: Grant
    Filed: July 11, 1995
    Date of Patent: November 5, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrike Schloesser, Udo Mayer
  • Patent number: 5554738
    Abstract: 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: Grant
    Filed: October 18, 1991
    Date of Patent: September 10, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Jean-Marie Adam, Adolf K aser
  • Patent number: 5549853
    Abstract: 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: Grant
    Filed: June 6, 1994
    Date of Patent: August 27, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Stefan Beckmann, Karl-Heinz Etzbach, Karl Siemensmeyer, Ruediger Sens
  • Patent number: 5527889
    Abstract: 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: Grant
    Filed: April 17, 1995
    Date of Patent: June 18, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Jurgen Schaetzer, James C. Posey
  • Patent number: 5420258
    Abstract: 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: Grant
    Filed: August 23, 1993
    Date of Patent: May 30, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Jurgen Schaetzer, James C. Posey
  • 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: 5298036
    Abstract: 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: Grant
    Filed: July 14, 1992
    Date of Patent: March 29, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Dieter Mausezahl, Urs Lehmann
  • Patent number: 5281263
    Abstract: 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: Grant
    Filed: January 21, 1992
    Date of Patent: January 25, 1994
    Assignee: Imperial Chemical Industries PLC
    Inventors: Peter Gregory, Prahalad M. Mistry
  • Patent number: 5278293
    Abstract: 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: Grant
    Filed: October 31, 1990
    Date of Patent: January 11, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Josef Herd, Manfred Hoppe, Hermann Henk, Klaus Kunde, Frank-Michael Stuohr
  • Patent number: 5262527
    Abstract: 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: Grant
    Filed: June 28, 1991
    Date of Patent: November 16, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Peter Gregory, Ronald W. Kenyon, Prahalad M. Mistry
  • Patent number: 5262330
    Abstract: 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: Grant
    Filed: February 27, 1992
    Date of Patent: November 16, 1993
    Assignee: Miles Inc.
    Inventors: Eddy Chapoteau, Bronislaw P. Czech, Wolodymyr I. Zazulak
  • Patent number: 5258505
    Abstract: 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: Grant
    Filed: March 27, 1992
    Date of Patent: November 2, 1993
    Assignee: Canon Kabushiki Kaisha
    Inventors: Tsuyoshi Eida, Mayumi Yamamoto, Takao Yamamoto
  • Patent number: 5254675
    Abstract: 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: Grant
    Filed: January 3, 1992
    Date of Patent: October 19, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Peter Gregory, Prahalad M. Mistry, David Greenwood
  • Patent number: 5243033
    Abstract: 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: Grant
    Filed: January 13, 1992
    Date of Patent: September 7, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanassios Tzikas
  • Patent number: 5225545
    Abstract: 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: Grant
    Filed: May 12, 1992
    Date of Patent: July 6, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Urs Lauk
  • Patent number: 5198022
    Abstract: 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: Grant
    Filed: January 17, 1992
    Date of Patent: March 30, 1993
    Assignee: 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
  • Patent number: 5185435
    Abstract: 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: Grant
    Filed: January 30, 1992
    Date of Patent: February 9, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Klaus Ruf, Bilge Gulec, Michael Reisinger, Werner Surber
  • Patent number: 5177195
    Abstract: 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: Grant
    Filed: January 3, 1992
    Date of Patent: January 5, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Peter Gregory, Prahalad M. Mistry
  • Patent number: 5175258
    Abstract: 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: Grant
    Filed: December 14, 1990
    Date of Patent: December 29, 1992
    Assignee: Xerox Corporation
    Inventors: Kock-Yee Law, Ihor W. Tarnawskyj
  • Patent number: 5149366
    Abstract: 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: Grant
    Filed: October 9, 1991
    Date of Patent: September 22, 1992
    Assignees: Sumitomo Chemical Company, Limited, Taoka Chemical Company
    Inventors: Hideo Kawashita, Mituhiro Ohta, Kazuya Ogino
  • Patent number: 5145953
    Abstract: 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: Grant
    Filed: February 2, 1988
    Date of Patent: September 8, 1992
    Assignee: The Dow Chemical Company
    Inventors: Robert A. Kirchhoff, Alan K. Schrock
  • Patent number: 5075429
    Abstract: 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: Grant
    Filed: October 10, 1989
    Date of Patent: December 24, 1991
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Jun Yamamoto, Yasuyoshi Ueda, Takashi Omura, Yosuke Yamamoto, Hideo Hattori, Junichi Sekihachi
  • Patent number: 5053495
    Abstract: 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: Grant
    Filed: August 24, 1989
    Date of Patent: October 1, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: David Greenwood, Nigel Hughes, Ronald W. Kenyon, Suraj L. Hindagolla
  • 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: 4994563
    Abstract: 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: Grant
    Filed: June 27, 1989
    Date of Patent: February 19, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Harald Walter, Rudolf Hurter
  • Patent number: 4988805
    Abstract: 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: Grant
    Filed: July 14, 1988
    Date of Patent: January 29, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus Kunde
  • Patent number: 4978747
    Abstract: 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: Grant
    Filed: April 13, 1989
    Date of Patent: December 18, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Arnold Weber, Hermann Henk, Klaus Kunde, Jochen Westphal, Klaus Wunderlich
  • Patent number: 4965345
    Abstract: 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: Grant
    Filed: October 2, 1987
    Date of Patent: October 23, 1990
    Assignee: BASF Aktiengesellschaft
    Inventor: Hermann Loeffler
  • Patent number: 4956457
    Abstract: 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: Grant
    Filed: August 10, 1989
    Date of Patent: September 11, 1990
    Inventor: Takeo Takayanagi
  • Patent number: 4910299
    Abstract: 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: Grant
    Filed: December 2, 1987
    Date of Patent: March 20, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Angelo D. Casa, Peter Liechti, Max Dempfle
  • Patent number: 4904765
    Abstract: 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: Grant
    Filed: July 14, 1987
    Date of Patent: February 27, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Derber, Rudolf Denninger
  • Patent number: 4863910
    Abstract: 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: Grant
    Filed: May 20, 1986
    Date of Patent: September 5, 1989
    Inventor: Takeo Takayanagi
  • Patent number: 4861344
    Abstract: 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: Grant
    Filed: October 30, 1987
    Date of Patent: August 29, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ludwig Schlafer, Hartmut Springer, Reinhard Hahnle
  • Patent number: 4841037
    Abstract: 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: Grant
    Filed: June 10, 1986
    Date of Patent: June 20, 1989
    Assignees: Canon Kabushiki Kaisha, Mitsubishi Chemical Industries Limited
    Inventors: Tokuya Ohta, Masatsune Kobayashi, Yuko Suga, Konoe Miura, Hiroshi Takimoto, Tomio Yoneyama
  • 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: 4754020
    Abstract: 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: Grant
    Filed: March 7, 1986
    Date of Patent: June 28, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Joachim Wolff, Karlheinz Wolf, Reinhold M. Klipper, Peter M. Lange
  • Patent number: 4752337
    Abstract: 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: Grant
    Filed: June 5, 1987
    Date of Patent: June 21, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus Kunde
  • Patent number: 4734218
    Abstract: 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: Grant
    Filed: July 18, 1986
    Date of Patent: March 29, 1988
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Keisuke Takuma, Kimitoshi Kato, Hiroshi Aiga, Yasuyuki Yamada, Tsutomu Nishizawa
  • Patent number: 4703113
    Abstract: 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: Grant
    Filed: August 12, 1985
    Date of Patent: October 27, 1987
    Assignee: Imperial Chemical Industries PLC
    Inventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
  • Patent number: 4694075
    Abstract: 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: Grant
    Filed: January 21, 1986
    Date of Patent: September 15, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Colberg, Erwin Hahn
  • Patent number: 4676923
    Abstract: 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: Grant
    Filed: December 2, 1985
    Date of Patent: June 30, 1987
    Assignee: Kabushiki Kaisha Nippon Kanko Shikiso Kenkyusho
    Inventors: Shigeo Yasui, Masashi Ono, Seiko Kobayashi, Shigeo Senzai, Tatsuo Uchida
  • Patent number: 4663440
    Abstract: 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: Grant
    Filed: May 26, 1981
    Date of Patent: May 5, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takashi Omura, Masaki Sunami, Yasuo Tezuka
  • 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: 4645832
    Abstract: 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: Grant
    Filed: April 9, 1985
    Date of Patent: February 24, 1987
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Toshio Niwa, Yoshiaki Kato