Oxygen Bonded Directly To The Sulfonyl Group (e.g., Sulfonic Acid, Etc.) Patents (Class 534/845)
  • Patent number: 10301474
    Abstract: Dyes of formula (1) their production and their use are described.
    Type: Grant
    Filed: September 10, 2015
    Date of Patent: May 28, 2019
    Assignee: DyStar Colours Distribution GmbH
    Inventors: Adrian Murgatroyd, Manfred Hoppe, Clemens Grund
  • Publication number: 20130078186
    Abstract: The present invention relates to compounds suitable as modulators of protein misfolding and/or protein aggregation. The compounds are particularly suitable as inhibitors of amyloid aggregate formation and/or modulators of amyloid surface properties, and/or as activators of degradation or reduction of amyloid aggregates.
    Type: Application
    Filed: March 23, 2011
    Publication date: March 28, 2013
    Applicant: MAX-DELBRUECK-CENTRUM FUER MOLEKULARE MEDIZIN
    Inventors: Erich Wanker, Thomas Wiglenda, Julius Tachu Babila, Annett Boeddrich, Michael Schmidt, Franziska Schiele
  • Publication number: 20040198964
    Abstract: The invention relates to novel monoazo compounds of formula (1), wherein R1 represents H, Cl or CH3; R2 represents H or Cl; M2+ represents Mg2+, Mn2+ or Sr2+; Y1=represents COO− or SO3−; Y2═SO3−, Y3═Y4═Y5═H; or Y3═SO3−, Y2═Y4═Y5═H; or Y4═SO3−, Y2═Y3═Y5═H; or Y5═SO3−, Y2═Y3═Y4═H. The compounds of formula (1) are characterized by high intensity and lightfastness.
    Type: Application
    Filed: February 13, 2004
    Publication date: October 7, 2004
    Inventors: Hans Joachim Metz, Uday T. Nabar, Frank Morgenroth, Chandrashekhar D Patil, Sunil D. Deval
  • Publication number: 20040139880
    Abstract: The invention relates to novel monoazo compounds of formula (1), wherein R represents H or Cl, M2+ represents Ca2+ or Sr2+ and Y1=H and Y2=SO3− or Y1=SO3− and Y2=H. The compounds of formula (1) are characterized by their high dying power and high light-fastness.
    Type: Application
    Filed: November 5, 2003
    Publication date: July 22, 2004
    Inventors: Hans Joachim Metz, Uday T. Nabar, Frank Morgenroth, Chanrashekhar D. Patil, Sunil D. Deval
  • Patent number: 6583273
    Abstract: This invention relates to dyes of formula wherein R1 is hydrogen, halogen, C1-C8alkyl, —NH—CO—C1-C4alkyl or phenyl, R2 is hydrogen, halogen, C1-C8alkyl, C1-C8alkoxy, —NH—CO—C1-C4alkyl or phenyl, R3 is hydrogen, C1-C8alkyl or phenyl, R4 is hydrogen, halogen or C1-C8alkyl, and X is —CO—, — COO—or —SO2—, and n is the number 1 or 2, to their preparation and to their use for dyeing or printing natural and synthetic materials, in particular synthetic polyamide fibre materials.
    Type: Grant
    Filed: May 4, 2000
    Date of Patent: June 24, 2003
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Jean-Pierre Bacher, Jean-Marie Adam
  • Patent number: 6395885
    Abstract: The use of lithium as a cation for an anionic dye to enhance the light-fastness of the dye. Also claimed are the lithium salts of certain anionic dyes as defined in the description; mixed lithium/sodium salts of an anionic dye wherein the molar ratio of lithium to sodium is from 1:4 to 99:1 and at least 20 mole % of the total counter ions in the dye are lithium cations; inks containing the dyes; a method of ink jet printing using the inks; a substrate printed with the inks; an ink jet printer cartridge containing the ink and a ink jet printer containing the ink jet printer cartridge.
    Type: Grant
    Filed: December 5, 2000
    Date of Patent: May 28, 2002
    Assignee: Avecia Limited
    Inventors: Aidan Joseph Lavery, Janette Watkinson, John Parker Meyers
  • Patent number: 6241789
    Abstract: Process for dyeing or printing paper, films of plastic or fibre material containing hydroxyl groups or containing nitrogen with reactive dyes, which comprises using at least one reactive dye of the formula (1) from the following group a) and at least one reactive dye from the following groups b), c) and d): a) green- or blue-dyeing reactive dyes of the formula (1) b) blue-dyeing reactive dyes of the formula (2) or (3) c) red-dyeing reactive dyes of the formula (4) d) yellow- or orange-dyeing reactive dyes of the formula (5)
    Type: Grant
    Filed: April 3, 2000
    Date of Patent: June 5, 2001
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Peter Scheibli, Peter Aeschilmann, Urs Lehmann, Marcel Frick
  • Patent number: 6124504
    Abstract: The application describes a process for preparing 4-hydroxyanilines by the reaction of phenols with diazonium salts and subsequent reduction.
    Type: Grant
    Filed: June 27, 1997
    Date of Patent: September 26, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Achim Hupperts, Karl Steinbeck, Uwe Stelzer, Reinhard Lantzsch, Hermann Seifert
  • Patent number: 6096889
    Abstract: An aromatic amino sulfonic acid compound is purified by a process including steps of:(a) dissolving the aromatic amino sulfonic acid compound in aqueous medium having a basic pH;(b) acidifying the aqueous medium with acetic acid to precipitate the aromatic amino sulfonic acid compound; and(c) removing the precipitated aromatic amino sulfonic acid compound from the aqueous medium.Using acetic acid in the process results in removal of more impurities and undesirable sulfate and chloride salts to provide an improved material for synthesizing dyes and pigments.
    Type: Grant
    Filed: June 1, 1999
    Date of Patent: August 1, 2000
    Assignee: BASF Corporation
    Inventors: Kevin P. Cusack, Louis Molinsek
  • Patent number: 6045593
    Abstract: The invention is a composition of matter useful as an acid yellow dye having formula (I) ##STR1## wherein: X is hydrogen or SO.sub.3.sup.- M.sup.+ ; M.sup.+ Na.sup.+, Li.sup.+, K.sup.+, NH.sub.4.sup.+, or hydroxyalkylammonium of the formula [H--(OCH.sub.2 CH.sub.2).sub.n ].sub.p NH.sub.m, where n is 1 to 5, p is 1 to 3, and p+m is 4; R.sub.1 is hydrogen, a metal ion, an alkyl or C.sub.1-4, of hydroxyalkyl of C.sub.1-4, and combinations thereof; and R.sub.2 is an unsubstituted aromatic ring or a substituted aromatic ring having at least one substituent, provided that when one of the substituents is SO.sub.3.sup.- M.sup.+, X is hydrogen; and combinations thereof. The invention also includes a process for dyeing a material with this compound and the material so dyed.
    Type: Grant
    Filed: April 27, 1999
    Date of Patent: April 4, 2000
    Inventor: Howard L. Smith
  • Patent number: 5719270
    Abstract: Azophenyl compounds of the formula: ##STR1## wherein R.sub.1 is an o-, p-directing substituent; R.sub.2 is a substituted or unsubstituted .beta.-hydroxyalkyl group; R.sub.3 is an aromatic carbocyclic or heterocyclic group which is mono- or poly-cyclic and is substituted or unsubstituted; and wherein the benzene ring A may contain one or more further substituents. The compounds are useful as dyestuffs (if they are themselves colored) or as intermediates in the preparation of dyestuffs.
    Type: Grant
    Filed: January 15, 1997
    Date of Patent: February 17, 1998
    Inventors: Steven Michael Partington, David Allan Clarke
  • Patent number: 5644040
    Abstract: Azo dyes of the formula (1) ##STR1## in which R.sub.1 and R.sub.2 are hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkanoylamino, ureido or halogen, X is chlorine or fluorine, B.sub.1 is phenyl, naphthyl or heterocyclic radical, and A.sub.1 is a radical of the formula (2) ##STR2## in which R.sup.7 is hydrogen, amino, N-mono- or N,N-di-C.sub.1 -C.sub.4 alkylamino or optionally substituted phenylamino and R.sub.8 is hydrogen or hydroxyl, or A.sub.1 is a radical of the formula (3) ##STR3## in which R.sub.9 is hydrogen, C.sub.1 -C.sub.8 alkyl or phenyl which is optionally substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.2 -C.sub.4 alkanoylamino, ureido, halogen or sulfo, R.sub.10 is hydrogen or C.sub.1 -C.sub.8 alkyl and R.sub.11 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.
    Type: Grant
    Filed: November 21, 1995
    Date of Patent: July 1, 1997
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Hurter
  • Patent number: 5510468
    Abstract: There are described benzophenoneazo dyes of the formula ##STR1## where the ring A can be benzofused and a benzofused ring A can be overbridges,m is 1 or 2,K is the radical of a coupling component,Y is hydrogen or arylazo,one of the two radicals X.sup.1 and X.sup.2 is hydrogen and the other is hydroxysulfonyl,R.sup.1, R.sup.2 and R.sup.3 are independently of the others hydrogen, halogen, C.sub.1 -C.sub.12 -alkyl, cyclohexyl, phenyl, 2-hydroxy-ethylsulfonyl or C.sub.1 -C.sub.4 -alkoxy or, when m is 1 and Y is hydrogen, one of these substituents can also be the radical of the formula ##STR2## where L.sup.1 is a chemical bond or a bridge member, and X.sup.1, X.sup.2, R.sup.4, K and the ring A are each as defined above, andR.sup.4 is hydrogen, halogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: July 27, 1994
    Date of Patent: April 23, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Gunther Lamm, Helmut Reichelt, Ortwin Schaffer
  • Patent number: 5486214
    Abstract: A biodegradable azo dye contains a nitrogen atom linked to an aromatic ring having a lignin-like substitution pattern. The ring is preferably a syringyl or guaiacol moiety, and provides a naturally-occurring structure for attack by microorganisms, such as Streptomyces or Phanerochaete. In especially preferred embodiments, the aromatic ring has a first substituent R.sub.1 selected from among hydroxy, lower alkoxy, or amino, and a second substituent R.sub.2 selected from among lower alkyl, lower alkoxy and halogen. Some embodiments include a third ring substituent R.sub.3 selected from the group lower alkyl, lower alkoxy, and halogen.
    Type: Grant
    Filed: August 12, 1992
    Date of Patent: January 23, 1996
    Assignee: Idaho Research Foundation, Inc.
    Inventors: Andrzej Paszczynski, Stefan Goszczynski, Ronald L. Crawford, Donald L. Crawford, Maria B. Pasti
  • Patent number: 5424403
    Abstract: Aminoazo dyes are prepared from the corresponding N-sulfomethylated aminoazo dyes by aqueous acid hydrolysis in the presence of amidosulfuric acid, urea or mixtures thereof.
    Type: Grant
    Filed: May 20, 1994
    Date of Patent: June 13, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Rudolf Bermes, Heinz Keilhauer
  • Patent number: 5382659
    Abstract: The invention relates to novel aromatic acids, especially to compounds of formula ##STR1## wherein R.sub.1 is lower alkyl, R.sub.2 is lower alkyl, R.sub.3 is hydrogen, carboxy or sulfo, R.sub.4 is carboxy or sulfo, G is an unsubstituted or substituted 1,4-phenylene group or an unsubstituted or substituted 1,4-naphthylene group, and wherein either R.sub.5 and R.sub.6 together are an additional bond and L is an oxygen or sulfur atom or wherein R.sub.5 is hydrogen, R.sub.6 is halomethyl and L is an oxygen atom, and salts thereof, to the use of compounds I and their salts, to a process for the preparation of compounds I and their salts, to starting materials used in that preparation process, and salts thereof, to a process for the preparation of those starting materials and their salts, to a device in which the compounds I and their salts are used, and to a process in which that device is used.
    Type: Grant
    Filed: June 7, 1994
    Date of Patent: January 17, 1995
    Assignee: Ciba-Geigy Corp.
    Inventor: Jui Y. Chang
  • Patent number: 5380859
    Abstract: There are described benzophenoneazo dyes of the formula ##STR1## where the ring A can be benzofused and a benzofused ring A can be overbridged,m is 1 or 2,K is the radical of a coupling component,Y is hydrogen or arylazo,one of the two radicals X.sup.1 and X.sup.2 is hydrogen and the other is hydroxysulfonyl,R.sup.1, R.sup.2 and R.sup.3 are independently of the others hydrogen, halogen, C.sub.1 -C.sub.12 -alkyl, cyclohexyl, phenyl, 2-hydroxyethylsulfonyl or C.sub.1 -C.sub.4 -alkoxy or, when m is 1 and Y is hydrogen, one of these substituents can also be the radical of the formula ##STR2## where L.sup.1 is a chemical bond or a bridge member, andX.sup.1, X.sup.2, R.sup.4, K and the ring A are each as defined above, andR.sup.4 is hydrogen, halogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: July 16, 1993
    Date of Patent: January 10, 1995
    Assignee: Basf Aktiengesellschaft
    Inventors: Gunther Lamm, Helmut Beichelt, Ortwin Schaffer
  • Patent number: 5340931
    Abstract: Allene compounds have the formula:(CH.sub.2 .dbd.C.dbd.CH--O).sub.n --R--(A).sub.m (I)in which R is a substituted or unsubstituted mono- or polyvalent benzene, naphthalene, anthracene, azobenzene, bisphenol or polyphenyl (containing 2 to 10 benzene rings connected in line) nucleus, or a group--Ph--R.sup.1 --Ph-- (II)(in which each group Ph is a phenylene, halophenylene, alkylphenylene, cyanophenylene or alkoxyphenylene group, and the chain R.sup.1 linking the two group Ph is a C.sub.1 -C.sub.6 aliphatic hydrocarbon or an alicyclic hydrocarbon group, the chain optionally being interrupted by one or more oxygen atoms); A is a carboxyl or sulphonyl group or a group --CH.dbd.C.dbd.CH.sub.2 ; n is an integer of from 1 to 10; m is 0, 1, 2 or 3; and the sum of m and n is equal to the valence of the group R.They may be prepared by isomerization of corresponding propargyloxy compounds.
    Type: Grant
    Filed: March 15, 1989
    Date of Patent: August 23, 1994
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Mitsuo Yamada, Hiromichi Kayano, Kei Aoki, Keizou Ishii
  • Patent number: 5278291
    Abstract: A process for the preparation of the sulphone of the formula ##STR1## consists in reductive cleavage of azo/azoxy dyestuffs of the formula ##STR2## where D is a radical of a diazo component from the benzene or naphthalene series.The invention also relates to the azo/azoxy dyestuffs mentioned.
    Type: Grant
    Filed: October 9, 1992
    Date of Patent: January 11, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventor: Karl-Josef Herd
  • 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: 5229503
    Abstract: The invention relates to azo compounds, especially to compounds of formula ##STR1## wherein R.sub.1 is lower alkyl, R.sub.2 is lower alkyl, R.sub.3 is hydrogen, carboxy or sulfo, R.sub.4 is carboxy or sulfo, G is an unsubstituted or substituted 1,4-phenylene group or an unsubstituted or substituted 1,4-naphthylene group, and wherein either R.sub.5 and R.sub.6 together are an additional bond and L is an oxygen or sulfur atom or wherein R.sub.5 is hydrogen, R.sub.6 is halomethyl and L is an oxygen atom, and salts thereof, to the use of compounds I and their salts, to a process for the preparation of compounds I and their salts, to starting materials used in that preparation process, and salts thereof, to a process for the preparation of those starting materials and their salts, to a device in which the compounds I and their salts are used, and to a process in which that device is used.
    Type: Grant
    Filed: September 11, 1991
    Date of Patent: July 20, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Jui Y. Chang
  • Patent number: 5106960
    Abstract: The present invention relates to azo dyes of the formula ##STR1## wherein X is an aryloxy radical or an unsubstituted or substituted C.sub.1 -C.sub.12 alkyl radical, a cycloalkyl radical or an aryl radical or a group of the formula ##STR2## wherein R.sub.1 is hydrogen, unsubstituted or substituted lower alkyl, cycloalkyl or aryl, and R.sub.2 is hydrogen or unsubstituted or substituted lower alkyl, or wherein R.sub.1 and R.sub.2, together with the nitrogen atom to which they are attached, form a 5- or 6-membered heterocyclic ring which may contain a further hetero-atom, Y is halogen, low molecular alkyl or low molecular alkoxy, and K is the radical of a coupling component of the benzene or naphthalene series or of the heterocyclic series.These dyes yield dyeings of good light- and wetfastness on polyamide material.
    Type: Grant
    Filed: March 22, 1991
    Date of Patent: April 21, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Rudolf Hurter, Dieter Mausezahl
  • Patent number: 4997919
    Abstract: This invention relates to direct dyes for various substrates, in particular cellulosic fiber materials. The inventive dyes are high-temperature-resistant and highly suitable for the single bath, one step dyeing of polyester/cotton mixed fabrics with a disperse dye for the polyester fibers under the dyeing conditions for polyester fibers.The inventive dyes are of the formula ##STR1## in which A is a radical of the formula ##STR2## A' has the meaning of A or is a mono- or polyazo dye radical which is different from A, R and R', independently of one another, are hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by chlorine, hydroxyl, cyano, carboxyl, sulfo, sulfato, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl, R.sub.1 is hydroxyl, C.sub.1 -C.sub.4 alkoxy, halogen, C.sub.1 -C.sub.4 alkylthio, amino, N-mono- or N,N-di-C.sub.1 -C.sub.4 alkylamino which is unsubstituted or substituted in the alkyl moiety by hydroxyl, carboxyl or C.sub.1 -C.sub.
    Type: Grant
    Filed: June 19, 1989
    Date of Patent: March 5, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Schaulin
  • 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: 4992532
    Abstract: The compounds of the formula ##STR1## where the substituents and indices are as defined in claim 1, are green direct dyes for various substrates, in particular cellulosic fibre materials. They are high-temperature stable and therefore are particularly highly suitable for the one-bath, single-stage dyeing of polyester/cotton blend fabrics together with a disperse dye for the polyester fibres under the dyeing conditions for polyester fibres.
    Type: Grant
    Filed: May 3, 1989
    Date of Patent: February 12, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Schaulin
  • Patent number: 4918183
    Abstract: The invention relates to monoazo dyes of the formula ##STR1## wherein K is the radical of a coupling component of the benzene, naphthalene or heterocyclic series, and R is hydrogen, halogen, carboxy, a C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.2 -C.sub.6 alkanoylamino, C.sub.1 -C.sub.6 alkylsulfonylamino, C.sub.1 -C.sub.6 alkylsulfonyl, phenyl(C.sub.1 -C.sub.4)alkylsulfonyl or naphthyl(C.sub.1 -C.sub.4)alkylsulfonyl or benzoyl radical, which radicals may be further substituted, or is a ##STR2## group, wherein each of R.sub.1 and R.sub.2 independently of the other is hydrogen or a C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or naphthyl radical, which radicals may be further substituted, and wherein X is hydrogen, halogen or a C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.2 -C.sub.6 alkanoylamino or C.sub.1 -C.sub.6 alkylsulfonylamino radical, which radicals may be further substituted.These dyes give dyeings of good light- and wetfastness properties on polyamide material.
    Type: Grant
    Filed: October 24, 1985
    Date of Patent: April 17, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Hurter
  • Patent number: 4906740
    Abstract: The present invention relates to monoazo dyes which dye polyamide material with good light- and wet-fastness and which have the formula ##STR1## in which K is the radical of an amino- or alkoxy-benzene, amino- or alkoxy-naphthalene, naphthol, aminonaphthol, pyrazolone, aminopyrazole, indole, naphthimidazole, diphenylamine, tetrahydroquinoline or acetoacetamide and can be further substituted, R is hydrogen, halogen, C.sub.1-6 -alkyl, trifluoromethyl, carboxyl or a --SO.sub.2 --C.sub.1-6 --alkyl, --SO.sub.2 --R.sub.1, ##STR2## --CO--R.sub.4 group, in which R.sub.1 is a substituted or unsubstituted phenyl- or naphthyl-C.sub.1-4 -alkyl radical, R.sub.2 and R.sub.3 independently of one another are hydrogen or a substituted or unsubstituted C.sub.1-6 -alkyl or C.sub.5-7 -cycloalkyl radical and R.sub.4 is a substituted or unsubstituted phenyl radical, and X is hydrogen, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy or halogen, and in which R in formula (1) may not be hydrogen or chlorine if the radical --N.dbd.
    Type: Grant
    Filed: July 15, 1986
    Date of Patent: March 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Hurter
  • Patent number: 4873321
    Abstract: A monoazo compound of the following formula, ##STR1## wherein A is phenyl or naphthyl, B.sub.1 and B.sub.2 are each phenylene or naphthylene, R.sub.1 is hydrogen, halogeno, alkyl, alkoxy, ureido or acylamino, R.sub.2 is hydrogen or takes together with R.sub.1 to form benzene, R.sub.3 is hydrogen, alkyl, alkoxy or sulfo, R.sub.4 and R.sub.5 are each hydrogen or alkyl, and Y.sub.1 and Y.sub.2 are each vinyl, sulfatoethyl or the like, which is useful for dyeing hydroxyl group-containing and amide-containing fiber materials to obtain dyed products of excellent fastness properties with excellent build-up property and reproducibility of dyeing irrespective of changes in dyeing temperatures, bath ratio or salt concentration in some degree.
    Type: Grant
    Filed: September 29, 1987
    Date of Patent: October 10, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takashi Omura, Sadanobu Kikkawa, Toshihiko Morimitsu, Naoki Harada, Tetsuya Miyamoto
  • Patent number: 4843151
    Abstract: The monoazo dyes of the formula ##STR1## in which K is the radical of a coupling component of the aminobenzene, alkoxybenzene, hydroxybenzene, pyrazolone, aminopyrazole, pyrimmidine, indole, diphenylamine or acetoacetamide series, R is a substituted or unsubstituted C.sub.1-12 alkyl, cycloalkyl, aralkyl or aryl radical, X is a --CO-- or --SO.sub.2 -- group, a --COO-- group, R being attached to the oxygen atoms, or an --SO.sub.2 NH-- or ##STR2## group, R being attached to the nitrogen atom and Y being hydrogen or C.sub.1-4 alkyl, and Z is hydrogen or C.sub.1-4 alkyl, produce dyeings having good fastness to light and wet processing on polyamide material.
    Type: Grant
    Filed: April 9, 1987
    Date of Patent: June 27, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Hurter
  • Patent number: 4841009
    Abstract: Described herein are novel substantially linear monomeric compositions which can be polymerized with one or more difunctional monomers to give novel polymeric compositions having liquid crystal properties. This invention is also directed to a process for preparation of the novel substantially linear monomeric compositions.
    Type: Grant
    Filed: July 5, 1985
    Date of Patent: June 20, 1989
    Assignee: Amoco Corporation
    Inventor: Donald R. Kelsey
  • Patent number: 4835284
    Abstract: This invention relates to a method for preparing 2-phenylbenzotriazoles having the formula I, ##STR1##
    Type: Grant
    Filed: January 27, 1988
    Date of Patent: May 30, 1989
    Assignee: Chemipro Kasei Kaisha, Ltd.
    Inventor: Shuichi Seino
  • Patent number: 4772687
    Abstract: Metal complex dyestuffs which in the form of the free acid correspond to the formula ##STR1## in which the substituents have the meaning given in the description are, depending on the meanings of the substituents, suitable for use as reactive dyestuffs for cotton, wool or polyamide, as direct dyestuffs for cotton or as pigment dyestuffs. Dyeings are obtained which have good fastness properties, in particular good wet-, light- and chlorine fastness.
    Type: Grant
    Filed: May 1, 1986
    Date of Patent: September 20, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hermann Henk
  • Patent number: 4749813
    Abstract: 4-Alkyl-2-trifluoromethylanilines, in particular the 4-isopropyl derivative, are starting materials for preparing valuable azo dyestuffs. While the nonionic dyestuff types can preferably be used in transfer printing synthetic hydrophobic fibre materials, the sulpho-containing dyestuffs--in particular those based on "gamma acid"--are suitable for dyeing polyamides.
    Type: Grant
    Filed: December 30, 1982
    Date of Patent: June 7, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Gerhard Wolfrum
  • Patent number: 4748236
    Abstract: Reactive azo dyestuffs of the formula ##STR1## wherein D . . . radical of the benzene or naphthalene series, having a sulpho group in the o-position to the azo bridge,K . . . radical of a coupling component of the benzene, naphthalene, pyridone, pyrazolone or hydroxynaphthalene series, or an aryl-azo-aryl radical,R . . . hydrogen or C.sub.1 -C.sub.4 -alkyl,Y . . . OR.sub.1 or SR.sub.1, R.sub.1 representing an optionally substituted alkyl, aryl or heteroaryl radical, or NR.sub.2 R.sub.3, R.sub.2 representing hydrogen or an optionally substituted alkyl radical and R.sub.3 representing hydrogen or an optionally substituted alkyl or aryl radical, or R.sub.2 and R.sub.3 forming a ring, optionally with inclusion of a hetero-atom, andX . . . halogen, such as chlorine or fluorine and their use for dyeing and printing materials containing hydroxyl groups or containing amide groups.
    Type: Grant
    Filed: November 9, 1984
    Date of Patent: May 31, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Jager, Richard Schwaebel
  • 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
  • Patent number: 4602084
    Abstract: Monoazo dyes of the formula ##STR1## in which K is the radical of a coupling component of the benzene or naphthalene series or of the heterocyclic series, and R is a ##STR2## --CO--R.sub.2 or --SO.sub.2 --O--R.sub.2 group in which R.sub.1 is hydrogen or C.sub.1-4 -alkyl and R.sub.2 is a substituted or unsubstituted monosulfo-C.sub.1-12 -alkyl radical, a substituted or unsubstituted monosulfophenyl, disulfophenyl, monosulfonaphthyl or disulfonaphthyl radical, and X and Y, independently of each other, are hydrogen, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, halogen, C.sub.2-6 -alkanoylamino, C.sub.1-5 -alkylsulfonylamino or a substituted or unsubstituted phenyl or phenoxy radical, produce dyeings on polyamide material which have good light and wet fastness properties.
    Type: Grant
    Filed: July 8, 1983
    Date of Patent: July 22, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Hurter
  • Patent number: 4585460
    Abstract: Reactive dyes of the formula ##STR1## wherein Y is a --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --X radical, in which X is a leaving group, and Z is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or carboxy, and K is the radical of a coupling component which couples at pH.ltoreq.7, are suitable for dyeing and printing textile fibre material and give dyeings and prints of good fastness properties.
    Type: Grant
    Filed: September 30, 1983
    Date of Patent: April 29, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Hansrudolf Schwander, Jurgen Markert, Peter Aeschlimann
  • Patent number: 4582897
    Abstract: Monoazo dyes of the formula ##STR1## in which K is a radical of the formula ##STR2## or of the formula ##STR3## in which R.sub.1 and R.sub.2 independently of one another is (sic) hydrogen, C.sub.1-4 -alkyl, which can be substituted by halogen, cyano, hydroxyl, carboxyl, sulfo, sulfato, C.sub.1-4 -alkoxy, C.sub.1-4 -alkoxycarbonyl, C.sub.1-4 -alkanoyloxy, phenyl, sulfophenyl and naphthyl, or cyclohexyl, or C.sub.1-4 -alkenyl, which can be substituted by halogen, or phenyl or naphthyl, or in which R.sub.1 and R.sub.2, together with the nitrogen atom connecting them and where relevant with the inclusion of a further hetero-atom, form a heterocyclic 5-membered or 6-membered ring, R.sub.3 is hydrogen, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, which can be substituted by hydroxyl and C.sub.1-4 -alkoxy, or C.sub.1-4 -alkanoylamino, or benzoylamino, which can be substituted in the benzene nucleus by methyl, ethyl, methoxy, ethoxy, chlorine, carboxyl and sulfo, or ureido, C.sub.
    Type: Grant
    Filed: May 2, 1984
    Date of Patent: April 15, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Dieter Mausezahl, Rudolf Hurter, Hansrudolf Schwander
  • Patent number: 4563518
    Abstract: The invention relates to fibre-reactive monoazo dyestuffs of the general formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 and n have the meaning given in the text of the application, and also relates to a process for the preparation of these dyestuffs and their use for dyeing and printing materials containing hydroxyl groups or amide groups, such as wool and cotton.
    Type: Grant
    Filed: October 20, 1980
    Date of Patent: January 7, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hermann Henk
  • Patent number: 4552951
    Abstract: This invention relates to azo dyes which may be unsubstituted or substituted with a variety of groups known to the dye art, and containing a diazonium moieties from an aniline type compound and certain coupler moieties from aniline, tetrahydroquinoline, or benzomorpholine compounds, wherein the diazonium moiety has one or two cinnamoyl substituents, and wherein one or more water-solubilizing groups such as a sulfonic acid group or its metal or amine salt may be present as a substituent in the dye molecule for acid dyeing. These dyes are particularly useful in dyeing one or more of polyamide cellulose acetate polyester, wool and other fibers.
    Type: Grant
    Filed: January 23, 1984
    Date of Patent: November 12, 1985
    Assignee: Eastman Kodak Company
    Inventor: Robert N. Gourley
  • Patent number: 4541831
    Abstract: Described is a process for the production of substantially dustless water-soluble dye or optical brightener compositions, which process comprises mixing a dry, solid inorganic salt, heated to at least 50.degree. C., with a mixture of at least one dye or optical brightener, an adhesive as e.g. sorbitol, a dust binding surface active agent and further additives. Such compositions are negligibly dusty to dustfree, and retain these properties even after storage for months, particularly in the case where spray-dried material is used.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: September 17, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Walter Gunther, Kurt Hintermayr
  • Patent number: 4530724
    Abstract: The color of azo pigments derived from 2-hydroxynaphthalene-3-carboxylic acid or its salts are improved by the coupling reaction of a diazonium compound of an aromatic aminosulfonic acid with a coupling component which is a mixture of (1) 2-hydroxynaphthalene-3-carboxylic acid or its salt, (2) .beta.-naphthol or its salt, and (3) a phenolic by-product having a molecular weight of about 300 and containing about 1 equivalent of phenolic hydroxy groups. The phenolic by-product can be obtained by evaporating .beta.-naphthol from a tarry substance formed as a by-product during the reaction of an alkali .beta.-naphtholate with carbon dioxide, extracting the residue with an alkali and precipitating the soluble matter with an acid. The color or tone of the azo pigment is stabilized by the use of the coupling component.
    Type: Grant
    Filed: September 1, 1982
    Date of Patent: July 23, 1985
    Assignee: Kabushiki Kaisha Ueno Seiyaku Uno Kenkyujo
    Inventors: Ryuzo Ueno, Hiroaki Tsuchiya, Shigeru Itoh
  • Patent number: 4486347
    Abstract: The halogenated azo dyestuffs of the present invention possess fire-proofing and antimicrobial properties and have the following general formula: ##STR1##
    Type: Grant
    Filed: January 22, 1982
    Date of Patent: December 4, 1984
    Assignee: Tsentralny Nauchnoissledovatelsky Institut Shersti
    Inventors: Irina N. Gorbacheva, Ljudmila M. Sukhova, Zinaida J. Kozinda, Vladislav L. Molokov, Lev T. Antonov, Vadim D. Simonov, Viktor A. Chertov, Semen I. Dvoskin, Raisa S. Veseneva