The Hetero Ring Contains The Pentavalent Nitrogen Patents (Class 534/607)
  • Patent number: 10640651
    Abstract: The present application relates to novel whitening agents for cellulosic substrates. The whitening agents are comprised of at least two constituents: at least one chromophore constituent and at least one polymeric constituent. Suitable chromophore components generally fluoresce blue, red, violet, or purple color when exposed to light, or they may absorb light to reflect these same shades. The whitening agents are further characterized by the polymeric component comprising at least two repeating glycerol units. This disclosure also relates to laundry care compositions including but not limited to liquid and/or powder laundry detergent formulations and rinse added fabric softening (RAFS) compositions that comprise such whitening agents.
    Type: Grant
    Filed: November 5, 2018
    Date of Patent: May 5, 2020
    Assignee: Milliken & Company
    Inventors: Eduardo Torres, Gregory Scot Miracle
  • Patent number: 8921564
    Abstract: The invention relates to basic bisazo compounds according to formula (I) wherein all substituents are defined as in Claim 1, their production, their use as dyestuffs as well as material dyed with these dyestuffs.
    Type: Grant
    Filed: July 25, 2007
    Date of Patent: December 30, 2014
    Assignee: Clariant Finance (BVI) Ltd.
    Inventors: Ludwig Hasemann, Friedrich Lehr, Martin Oberholzer, Heidrun Schene
  • Publication number: 20140237735
    Abstract: The invention relates to agents for coloring keratinic fibers, in particular human hair, including in a cosmetic carrier at least one compound of the formula (I). The structures the of the general formula (I) have a heterocycle A which bears a quaternary nitrogen atom and thus a positive charge. The invention furthermore relates to the use of these novel azo dyes in agents for coloring hair and to the dyes themselves.
    Type: Application
    Filed: May 5, 2014
    Publication date: August 28, 2014
    Applicant: Henkel AG & Co. KGaA
    Inventors: Wibke Gross, Ralph Nemitz, Melanie Moch
  • Publication number: 20140157529
    Abstract: Disclosed are compounds of formula (1) or formula (2). The compounds are useful for the dyeing of organic materials, such as keratin fibers, wool, leather, silk, cellulose or polyamides, especially keratin-containing fibers, cotton or nylon, and preferably hair, more preferably human hair. (1) (2).
    Type: Application
    Filed: May 2, 2012
    Publication date: June 12, 2014
    Applicant: BASF SE
    Inventors: Sophie Marquais-Bienewald, Christian Cremer, Beate Frohling
  • Patent number: 7939644
    Abstract: The present invention relates to dyes of the general formula CAT+ Y? (I), where Y? is an anion selected from the group of the cyanoborates, fluoroalkylphosphates, fluoroalkylborates or imidates and CAT+ is a cation selected from the group of the azine, xanthene, polymethine, styryl, azo, tetrazolium, pyrylium, benzopyrylium, thiopyrylium, benzothiopyrylium, thiazine, oxazine, triarylmethane, diarylmethane, methine, acridine, quinoline, isoquinoline or quaternary azafluorenone dyes, for colouring plastics and plastic fibres, for the preparation of flexographic printing inks, as ball-point pen pastes, as stamp ink, for colouring leather and paper, for use in data acquisition systems, reprography, in ink microfilters, in photogalvanics, laser technology and the photo industry.
    Type: Grant
    Filed: July 22, 2004
    Date of Patent: May 10, 2011
    Assignee: Merck Patent GmbH
    Inventors: Nikolai (Mykola) Ignatyev, Urs Welz-Biermann, Helge Willner, Maik Finze, Eduard Bernhardt, Andriy Kucheryna
  • Publication number: 20110088173
    Abstract: Disclosed are polymeric dyes obtained by the reaction of (a) a basic polycondensate with (b) an electrophilic dye of formula (2) P—X—Ya+ Ana?; wherein the basic polycondensate (a) is obtained by the reaction of (a1) an amine of formula (I) in the presence of an anhydrous solvent with an ammonium salt (a2) with a cyanamide; wherein R1, R2, R3 and R4 independently from each other are hydrogen; or C1-C4alkyl, which may be substituted by amino, hydroxy, cyano or C1-C4alkoxy; A is C2-C20alkylene, which may be substituted or interrupted by one or more than one hetero atoms; P is a reactive grouping capable of reacting with a nitrogen nucleophile; X is a linkage group selected from C1-C30alkylene, C2-C12alkenylene, C5-C10arylene, C5-C10cycloalkylene and C1-C10alkylene(C5-C10arylene) which may be interrupted and/or terminated at one or both ends by one or more than one —O—, —S—, —N?, —N(R5)—, —S(O)—, SO2, —(CH2CH2—O)1-5—, —(CH2CH2CH2—O)1-5—, —C(O)—, —C(O)O—, —OC(O)—, (II), —CON(R5)—, —C(NR5R6)2—, —(R5)NC(O)—, —C(S)R5
    Type: Application
    Filed: January 7, 2009
    Publication date: April 21, 2011
    Applicant: BASF SE
    Inventors: Sophie Marquais-Bienewald, Christian Cremer, Olof Wallquist, Roberg Hochberg
  • Patent number: 7892295
    Abstract: A disperse dye of formula (I): Wherein R1 and R2 independently are each (C1-C4)-alkyl, OH or (C1-C4)-alkoxy-substituted (C1-C4)-alkyl; R3 and R4 independently are each hydrogen or methyl; one of A and B is cyano and the other is —COOX; and X is (C2-C12)-alkyl, O-interrupted (C2-C12)-alkyl, (C3-C4)-alkenyl or phenyl-(C1-C4)-alkyl. The invention also relates to the preparation of the dye and the use of the dye.
    Type: Grant
    Filed: August 1, 2008
    Date of Patent: February 22, 2011
    Assignee: DyStar Colours Deutschland GmbH
    Inventor: Hartwig Jordan
  • Patent number: 7354572
    Abstract: A method of dyeing keratin-containing fibers, especially human hair, which comprises using dyes of formula (1), wherein X? is an anion.
    Type: Grant
    Filed: October 10, 2001
    Date of Patent: April 8, 2008
    Assignee: Ciba Specialty Chemicals Corp.
    Inventor: Peter Möckli
  • Patent number: 7307155
    Abstract: The present invention relates to novel the cationic dyes of formula (1) wherein R1 is an unsubstituted or substituted C1-C14 alkyl or an aryl radical; X? is an anion; R3 is an unsubstituted or substituted C1-C14 alkyl, aryl radical, C1-C6 alkoxy, cyanid, nitro or halide; n is 1 or 2; and if n is 1, then R2 is hydrogen, unsubstituted or substituted C1-C14 alkyl; or if n is 2, then R2 is an unsubstituted or substituted C1-C14 alkylen.
    Type: Grant
    Filed: July 14, 2004
    Date of Patent: December 11, 2007
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Victor Paul Eliu, Beate Fröhling
  • Patent number: 7166711
    Abstract: The present invention relates to novel cationic dye of formula (1) wherein R1 and R7 are each independently of the other hydrogen, hydroxyl; unsubstituted or substituted C1–C6alkyl, aryl radical or C114 C6alkoxy; or —NR3R4, wherein R3 and R4 are each independently of the other hydrogen, unsubstituted or substituted aryl radical or C1–C6alkyl, and R2 is hydrogen, hydroxyl, unsubstituted or substituted C1–C6alkyl, aryl radical or C1–C6alkoxy, —NR3R4, or an organic radical of formula (2) wherein R5 is hydrogen, unsubstituted or substituted aryl radical or C1–C6alkyl, and X? is an anion. Further, the present invention relates to compositions thereof, especially comprising other dyes, to processes for the preparation thereof and to the use thereof in the dyeing of organic material, such as keratin, wool, leather, silk, cellulose or polyamides, and preferably human hair.
    Type: Grant
    Filed: February 20, 2004
    Date of Patent: January 23, 2007
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Victor Paul Eliu, Beate Fröhling
  • Patent number: 7078498
    Abstract: The cationic dyes of formula (1) specified in claim 1 are suitable especially for colouring keratin-containing fibres, more especially for colouring hair.
    Type: Grant
    Filed: July 11, 2001
    Date of Patent: July 18, 2006
    Assignee: Cibe Specialty Chemicals Corporation
    Inventors: Peter Möckli, Beate Susanne Fröhling
  • Patent number: 7045608
    Abstract: A process for the preparation of certain cationic azo compounds is described, as well as the use thereof for dyeing keratin-containing fibres, especially human hair, in which specific cationic azo dyes are used.
    Type: Grant
    Filed: February 20, 2003
    Date of Patent: May 16, 2006
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Victor Paul Eliu, Julia Hauser
  • Patent number: 6949630
    Abstract: The cationic dyes of formula (1) specified in claim 1 are suitable especially for colouring keratin-containing fibres, more especially for colouring hair.
    Type: Grant
    Filed: September 17, 2002
    Date of Patent: September 27, 2005
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Jean-Marie Adam, Jean-Pierre Bacher
  • Patent number: 6762287
    Abstract: Dyes of formula (1) or (2) wherein R1, R1′, R2 and R2′ are each independently of the others hydrogen, C1-C4alkyl, halogen or nitro, R3, R3′, R4 and R4′ are each independently of the others C1-C4alkyl unsubstituted or substituted by OH, C1-C4alkoxy, halogen, CN or phenyl, R5 is hydrogen or C1-C4alkyl, R6 is unsubstituted or amino-substituted C5-C12alkyl; or unsubstituted or amino-substituted C5-C8cycloalkyl; or phenyl-substituted C1-C4alkyl; or wherein R5 and R6 together with the nitrogen atom linking them from a piperazine ring, which is substituted, at the nitrogen atom that is not bonded to the phenyl group, by C1-C4-alkyl or phenyl, the alkyl and phenyl radicals mentioned as substituents of the nitrogen atom of the piperazine ring being unsubstituted or substituted by amino, X1, X2, X3 and X4 are each independently of the others hydrogen, C1-C4alkyl, C1-C4alkoxy or halogen, Y1 is a bridging member of formula (I) or —NH—(CH2)6—NH—, and X− is an anion, as
    Type: Grant
    Filed: April 10, 2003
    Date of Patent: July 13, 2004
    Assignee: Ciba Specialty Chemicals Corporation
    Inventor: Peter Möckli
  • Patent number: 6518407
    Abstract: A novel reactive dye compound is disclosed. It comprises (a) at least one chromophore moiety; (b) at least one nitrogen-containing heterocycle; (c) a linking group to link each chromophore moiety to each nitrogen-containing heterocycle; characterised in that at least one nitrogen-containing heterocycle is substituted with at least one thio-derivative and at least one quaternized nitrogen derivative.
    Type: Grant
    Filed: February 13, 2001
    Date of Patent: February 11, 2003
    Assignee: The Procter & Gamble Company
    Inventors: Earl David Brock, David Malcolm Lewis, Taher Iqbal Yousaf
  • Patent number: 6399166
    Abstract: A liquid crystal display has a first substrate plate and a second substrate plate, and a liquid crystal layer disposed between the plates. A polarizing coating, having molecules of one or more organic dyes capable of forming a lyotropic liquid crystalline phase, is formed overlying a selected surface of each plate. Orientation of the polarizing coating is obtained by applying a force to the dye molecules when in the liquid crystal phase and subsequently converting the liquid crystal phase to a solid film.
    Type: Grant
    Filed: April 23, 1999
    Date of Patent: June 4, 2002
    Assignee: Optiva, Inc.
    Inventors: Ir Gvon Khan, Yuri A. Bobrov, Victor A. Bykov, Leonid Y. Ignatov, Pavel I. Lazarev
  • Patent number: 6049428
    Abstract: The present invention provides dyes of formula I-XXXIV, described in detail below, and dichroic light polarizers based on the dyes. In the dichroic light polarizers of this invention the dye molecules are aggregated into particles oriented in a predetermined direction on a surface of a substrate to enable the dye to polarize light transmitted through the dye. In another embodiment, a dichroic light polarizer includes a molecularly oriented layer of an organic dye on a surface of a substrate. The layer has a non-periodic arrangement of different polarizing elements. Each of the polarizing elements have differing orientations of the polarization vector in the substrate plane and/or differing colors. The dichroic light polarizer may contain one or more additional dye layers and may have a transparent layer intermediate to the dye layer.
    Type: Grant
    Filed: August 4, 1997
    Date of Patent: April 11, 2000
    Assignee: Optiva, Inc.
    Inventors: Ir G Khan, Yuri A. Bobrov, Leonid Y. Ignatov, Elena Y. Shishkina, Pavel I Lazarev, Alexey V. Kurbatov
  • Patent number: 5969112
    Abstract: A flocculating dye reduces bleed between two inks when they are applied side by side. A first ink comprises the flocculating dye which flocculates the dispersant-pigment of the second ink.
    Type: Grant
    Filed: April 3, 1998
    Date of Patent: October 19, 1999
    Assignee: Lexmark International, Inc.
    Inventors: James F. Feeman, Jing X. Sun
  • Patent number: 5952475
    Abstract: The novel cationic thiadiazolediphenylamine dyes of the formula (I) ##STR1## in which the substituents R.sup.1 to R.sup.9 have the meaning indicated in the description, and their anhydro bases, are suitable for use for inkjet printing and in light-writable data storage media and in dye transfer films.
    Type: Grant
    Filed: June 4, 1998
    Date of Patent: September 14, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventor: Horst Berneth
  • Patent number: 5919914
    Abstract: Clathrates of bis?6-hydroxy-4-methyl-5-(3-methyl-imidazolium-1-yl)-3-(phen-4-ylazo)pyrid in-2-one!ethylene with aromatics of the general formula I ##STR1## where R.sup.1 is C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.5 -hydroxyalkyl, C.sub.1 -C.sub.5 -alkoxy, C.sub.1 -C.sub.5 -hydroxyalkoxy, C.sub.1 -C.sub.10 -alkyl which is interrupted by 1, 2 or 3 non-neighboring oxygen atoms and is unsubstituted or substituted by hydroxyl, C.sub.1 -C.sub.10 -alkoxy which is interrupted by 1, 2 or 3 non-neighboring oxygen atoms and is unsubstituted or substituted by hydroxyl, or is C.sub.1 -C.sub.6 -alkanoyl, hydroxy, carboxyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, phenylcarbonyl or C.sub.1 -C.sub.6 -alkenyl andR.sup.2 is R.sup.1, hydrogen or phenoxy,a process for their preparation and their use for the preparation of formulations of the dye.
    Type: Grant
    Filed: March 17, 1998
    Date of Patent: July 6, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Manfred Ruske, Peter Erk, Heidi Hengelsberg
  • Patent number: 5883232
    Abstract: Disclosed are diazahemicyanine hydrophobic cationic dyes represented by the formula (1): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are lower alkyl groups having not more than 5 carbon atoms, R.sup.5 is a lower alkyl group having not more than 5 carbon atoms or a lower alkoxy lower alkyl group having not more than 6 carbon atoms, and Z.sup.- is a counter ion having a hydrophobic organic group, and a thermal transfer ink ribbon having a substrate and and ink layer laminated thereon containing said cationic dye.
    Type: Grant
    Filed: July 14, 1998
    Date of Patent: March 16, 1999
    Assignees: Sony Corporation, Hodog aya Chemical Co., Ltd.
    Inventors: Masanobu Hida, Kengo Ito, Yoshio Fujiwara, Nobuo Suzuki, Hiroyoshi Yamaga, Junichi Hagiwara
  • Patent number: 5866353
    Abstract: A variety of diazacyanine mediators that are soluble in aqueous media and which do not inhibit enzymatic activity are provided for use on the surface of a working electrode of a electrochemical biosensor for electrochemical co-enzyme regeneration. The co-enzyme, dihydronicotinamide adenine dinucleotide (NADH) or dihydronicotinamide adenine dinucleotide phosphate (NADPH), is oxidized to NAD.sup.+ OR NADP.sup.+ which is reduced by an oxidoreductase such as a dehydrogenase acting on a substrate. By applying the mediator together with NADH or NADPH to the surface of the working electrode, the voltage necessary to achieve oxidation is substantially reduced. Biosensor electrodes such as graphite electrodes may be produced-by screen printing techniques.
    Type: Grant
    Filed: December 9, 1996
    Date of Patent: February 2, 1999
    Assignee: Bayer Corporation
    Inventors: Horst Berneth, Thomas Bocker, Henry Giera, Alison J. Murray, Hans-Ulrich Siegmund
  • Patent number: 5834600
    Abstract: Disclosed are diazahemicyanine hydrophobic cationic dyes represented by the formula (1): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are lower alkyl groups having not more than 5 carbon atoms, R.sup.5 is a lower alkyl group having not more than 5 carbon atoms or a lower alkoxy lower alkyl group having not more than 6 carbon atoms, and Z.sup.- is a counter ion having a hydrophobic organic group,and a thermal transfer ink ribbon having a substrate and and ink layer laminated thereon containing said cationic dye.
    Type: Grant
    Filed: June 28, 1996
    Date of Patent: November 10, 1998
    Assignees: Sony Corporation, Hodogaya Chemical Co., Ltd.
    Inventors: Masanobu Hida, Kengo Ito, Yoshio Fujiwara, Nobuo Suzuki, Hiroyoshi Yamaga, Junichi Hagiwara
  • Patent number: 5591833
    Abstract: Colorants and compositions useful as a fugitive or permanent colorant for a variety of substrates, or as intermediates for their manufacture, and having one or more improved properties of enhanced aqueous washability, compatibility with and non-extractibility from thermoplastic resins, or reactivity with resins having reactive functionality, said composition having the formula C(Z).sub.
    Type: Grant
    Filed: August 10, 1993
    Date of Patent: January 7, 1997
    Assignee: Milliken Research Corporation
    Inventors: John B. Hines, David J. Moody, Edward W. Kluger
  • Patent number: 5580964
    Abstract: Cationic 1,3,4-thiadiazole dyestuffs of the formula ##STR1## in which the symbols used have the meaning given in the description, corresponding anhydrobases, processes for the preparation of the cationic 1,3,4-thiadiazole dyestuffs, their use for dyeing and printing various materials and as dichroic dyestuffs in polarizing films, and various materials which comprise such dyestuffs.
    Type: Grant
    Filed: March 23, 1995
    Date of Patent: December 3, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Berneth, Uwe Claussen, Werner Hartwich, Peter Wild
  • Patent number: 5502172
    Abstract: New pyrazole azo dyestuffs of the formula (I) ##STR1## in which R.sup.1 denotes hydrogen or an acyl radical,R.sup.2 denotes hydrogen, alkyl, alkenyl, cycloalkyl, aralkyl, aryl or a heterocyclic radical which is optionally bonded via alkylene,R.sup.3 denotes hydrogen, halogen, alkyl or alkoxy,R.sup.4 denotes hydrogen, halogen, hydroxyl, amino, nitro, cyano, alkyl, alkoxy, acylamino, acyloxy or alkoxy-carbonyl,R.sup.5 and R.sup.6 independently of one another in each case denote hydrogen, alkyl, aralkyl or aryl orNR.sup.5 R.sup.6 together denotes a hydrogenated heterocyclic radical which is bonded via the nitrogen and optionally contains further hetero atoms,it being possible for all the alkyl, alkenyl, cycloalkyl, aralkyl, aryl, alkoxy and heterocyclic radicals present to be optionally substituted by nonionic substituents, a novel process for their preparation and their use for dyeing and printing materials.
    Type: Grant
    Filed: April 6, 1995
    Date of Patent: March 26, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kerstin Pape, Horst Berneth
  • Patent number: 5446136
    Abstract: Pyrazole azo dyestuffs of the formula (I) ##STR1## in which R.sup.1 denotes hydrogen or an acyl radical,R.sup.2 denotes hydrogen, alkyl, alkenyl, cycloalkyl, aralkyl, aryl or a heterocyclic radical which is optionally bonded via alkylene,R.sup.3 denotes hydrogen, halogen, alkyl or alkoxy,R.sup.4 denotes hydrogen, halogen, hydroxyl, amino, nitro, cyano, alkyl, alkoxy, acylamino, acyloxy or alkoxycarbonyl,R.sup.5 and R.sup.6 independently of one another in each case denote hydrogen, alkyl, aralkyl or aryl orNR.sup.5 R.sup.6 together denotes a hydrogenated heterocyclic radical which is bonded via the nitrogen and optionally contains further hetero atoms,it being possible for all the alkyl, alkenyl, cycloalkyl, aralkyl, aryl, alkoxy and heterocyclic radicals present to be optionally substituted by nonionic substituents, a novel process for their preparation and their use for dyeing and printing materials.
    Type: Grant
    Filed: December 13, 1994
    Date of Patent: August 29, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kerstin Pape, Horst Berneth
  • Patent number: 5436323
    Abstract: Cationic 1,3,4-thiadiazolyldiphenylamine dyestuffs and corresponding anhydro bases, the dyestuffs having the formula (I) ##STR1## their preparation and their use, and materials dyed with such dyestuffs.
    Type: Grant
    Filed: July 1, 1993
    Date of Patent: July 25, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Berneth, Werner Hartwich, Karl-Heinrich Lange
  • Patent number: 5424404
    Abstract: Biscationic azo dyes useful for dyeing or printing polymeric material have the formula ##STR1## where R.sup.1 is hydrogen or unsubstituted or phenyl-substituted C.sub.1 -C.sub.5 -alkyl,R.sup.2 is hydrogen or C.sub.1 -C.sub.5 -alkyl,R.sup.3 and R.sup.4 are independently of each other hydrogen or methyl,D is the radical of a diazo component, unsubstituted or substituted phenylene or a radical of the formula ##STR2## where Z is a bridge member, Y is hydrogen, C.sub.1 -C.sub.18 -alkyl, C.sub.2 -C.sub.6 -alkylene, xylidene or phenylene,An.sup..crclbar.
    Type: Grant
    Filed: June 11, 1993
    Date of Patent: June 13, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Manfred Ruske, Udo Mayer
  • Patent number: 5352334
    Abstract: Metal-free compounds of the formula ##STR1## and 1:1 and 1:2 metal complexes thereof and acid addition salts of such metal-free compounds and 1:1 and 1:2 metal complexes,whereineach B is --A.sub.1 --NR.sub.7 R.sub.8 or --A.sub.1 --.sup..sym. NR.sub.7 R.sub.8 R.sub.9 A.sup..crclbar., the two B's being identical,whereineach A.sub.1 is linear or branched C.sub.2-8 alkylene,each R.sub.1 is hydrogen, C.sub.1-4 alkyl, C.sub.5-6 cycloalkyl, phenyl, benzyl or phenylethyl, the two R.sub.1 's being identical,each R.sub.2 is independently halo, hydroxy, nitro, carboxy, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,each T is hydrogen, cyano, --COOR.sub.4, --CON(R.sub.5).sub.2, --SO.sub.2 N(R.sub.5).sub.2,the two T's being identical, ##STR2## wherein each R.sub.3 is independently hydrogen, C.sub.1-4 alkyl, --N(R.sub.5).sub.2 or --CON(R.sub.5).sub.2,each R.sub.4 is C.sub.1-6 alkyl or phenyl(C.sub.1-3 alkyl),each R.sub.6 is C.sub.1-4 alkyl, andeach X.sub.a is --O--, --S-- or --NR.sub.5 --, andX.sub.
    Type: Grant
    Filed: November 25, 1992
    Date of Patent: October 4, 1994
    Assignee: Sandoz Ltd.
    Inventors: Helmut A. Moser, Roland Wald
  • Patent number: 5328994
    Abstract: New azinoneutromethines of the formula ##STR1## in which the symbols used have the meaning given in the description, a process for their preparation and their use in thermal and photochromic recording materials, as nonlinear optical materials, as photoconductors in electrophotography and for dyeing fibres and woven fabrics of polyester and plastics.
    Type: Grant
    Filed: February 19, 1993
    Date of Patent: July 12, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Berneth, Karin Hassenruck
  • Patent number: 5290921
    Abstract: The present invention provides primary hydroxyl enhanced colorants having markedly improved reactivities in e.g., polyurethane foams for imparting permanent coloring thereto, the colorants having the formulaC--(Z).sub.1-4are provided wherein C is an azo, methine, or azamethine chromogen and Z is a poly(oxyalkylene) moiety comprised of (1) at least two (A) units independently selected from those of the formulae--CH.sub.2 CH(O--T)CH.sub.2 O-- or --CH.sub.2 CH(O--T)CH.sub.2 O--Tand (2) from none to about 200 (B) units of the formula (--RO--) wherein R is straight or branched chain hydrocarbon of 2-4 carbons, T is a moiety of the formula--CH.sub.2 CH(R.sub.1)--O--(RO).sub.0-40 --CH.sub.2 CH.sub.2 OHwherein R.sub.1 is selected from unsubstituted or substituted alkyl, aryl, alkenyloxyalkyl, alkoxyalkyl or aryloxyalkyl, and wherein the A units comprise at least 0.5 percent of the total A+B units.
    Type: Grant
    Filed: January 8, 1990
    Date of Patent: March 1, 1994
    Assignee: Milliken Research Corporation
    Inventors: David J. Moody, Edward W. Kluger, John W. Rekers
  • Patent number: 5264560
    Abstract: Quaternized azo dyes whose diazo components are derived from a five-membered nitrogen-containing aromatic aminoheterocycle and whose coupling components are derived from the aniline series are prepared by reacting to corresponding neutral dye-bases with an alkylating agent in .gamma.-butyrolactone as inert diluent.
    Type: Grant
    Filed: July 17, 1992
    Date of Patent: November 23, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Guenter Hansen, Johannes P. Dix, Helmut Reichelt, Clemens Grund
  • Patent number: 5208325
    Abstract: Cationic 1,3,4-thiadiazole dyestuff of the formula ##STR1##in whichR.sup.1 and R.sup.2, independently of one another, denote hydrogen, alkyl, alkenyl, cycloalkyl, aralkyl, aryl, a heterocycle, said heterocycle having a direct bond to the nitrogen atom, or being bound through a methylene or ethylene group, or R.sup.1 and R.sup.2, together with the nitrogen atom to which they are attached form a heterocycle,R.sup.3 denotes alkyl, alkenyl or aralkyl,R.sup.4 denotes hydrogen or alkyl,R.sup.5 denotes acyl,R.sup.6 and R.sup.7, independently of one another, denote hydrogen, alkyl, alkoxy, aryloxy or halogen andR.sup.8 and R.sup.9, independently of one another, denote hydrogen, alkyl, alkenyl, cycloalkyl, aralkyl, aryl, a heterocycle, said heterocycle having a direct bond to the nitrogen atom, or being bound through a methylene or ethylene group, or R.sup.8 and R.sup.9, together with the nitrogen atom to which they are attached form a heterocycle, orR.sup.6 and R.sup.8 together with the nitrogen to which R.sup.
    Type: Grant
    Filed: December 11, 1991
    Date of Patent: May 4, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Berneth, Klaus Leverenz
  • Patent number: 5163972
    Abstract: Process to dye polyacrylonitrile in blue shades with cationic dye compounds: substituted benzothiazolium azo N-alkyl-N-hydroxyalkyl alkyl-aniline salts.
    Type: Grant
    Filed: December 3, 1990
    Date of Patent: November 17, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Wilfried Herter, Josef Koller
  • Patent number: 5073634
    Abstract: Basic dyes of the formulaChr.sup..sym.[FeCl.sub.4 ].sup..crclbar.where Chr.sup.a is a dye cation are useful for dyeing acrylonitrile polymers or acid-modified polyesters.
    Type: Grant
    Filed: May 1, 1990
    Date of Patent: December 17, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Johannes P. Dix, Guenter Hansen, Hellmut Kast
  • Patent number: 5023324
    Abstract: Disazo and trisazo compounds free of sulfo groups which contain 6-hydroxy-4-methyl-3-N-pyridiniumpyridone-2 coupling component radicals, the preferred compounds being of the formula ##STR1## wherein R is a tetrazo component radical,each R.sub.1 is independently hydrogen, C.sub.1-4 alkyl, C.sub.2-4 hydroxyalkyl the hydroxy group of which is in other than the 1-position or --NR.sub.3 R.sub.4, wherein each of R.sub.3 and R.sub.4 is independently n-C.sub.1-4 alkyl,each R.sub.2 is independently hydrogen, n-C.sub.1-4 alkyl, n-C.sub.1-4 hydroxyalkyl or C.sub.1-4 alkoxy, andeach A.sup..crclbar. is an anion,and liquid and granulated dye compositions comprising such compounds, are useful for dyeing paper and basically dyeable substrates such as polymers and copolymers of acrylonitrile and dicyanoethylene and synthetic polyesters and polyamides modified to contain acid groups. Dyeings on paper are brilliant and possess good light fastness and good fastness to water and alcohol.
    Type: Grant
    Filed: July 29, 1986
    Date of Patent: June 11, 1991
    Assignee: Sandoz Ltd.
    Inventor: Helmut Moser
  • Patent number: 5001229
    Abstract: Basic dyestuffs of the formula ##STR1## or tautomeric forms thereof, whereinR.sub.1 and R.sub.2 stand for hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen,Q - E stands for C-S, C-O, C-NH or N.sup..sym. -N.sup..crclbar.,A stands for C.sub.1 -C.sub.4 -alkylene,W stands for the radical of an aliphatic mono-, di-, tri-, tetra-, penta-, hexa- or heptamine, which can be protonated or quaternized,n stands for 0 to 1.5 andp stands for 1.3 to 10,are suitable for dyeing materials which can be dyed with basic dyestuffs.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: March 19, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Franke, Peter Wild
  • Patent number: 4925926
    Abstract: The invention relates to a continuous process for the preparation of cationic azo or hydrazone dyes from heterocyclic diazo components and coupling components. The diazo component is diazotised in water and an acid, the diazo solution is coupled with the coupling component and continuously alkylated, preferably using sufficient acid that, after the alkylation, a two-phase system forms, consisting of an aqueous solution which is substantially free from dye and a highly concentrated oil phase or solid dye.
    Type: Grant
    Filed: December 7, 1987
    Date of Patent: May 15, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Roland Ronco, Ermanno Ciapponi, Pierre Pessonneaux
  • Patent number: 4883866
    Abstract: Methine-azo compounds of the formula ##STR1## in which A is the complement to a heterocyclic 5- or 6-membered ring which has a quaternized N atom as a ring member, which can contain further hetero atoms and which can be substituted and/or fused with carbocyclic or heterocyclic rings,R is hydrogen, cyano or C.sub.2 -C.sub.3 -alkylene which is bonded to an N atom of ring A to form a 5- or 6-membered ring,B is substituted or unsubstituted phenylene or naphthylene,X.sup..crclbar.
    Type: Grant
    Filed: February 29, 1988
    Date of Patent: November 28, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Mockli
  • Patent number: 4840641
    Abstract: Cationic diazacyanine dyestuffs of the formula ##STR1## and their mixtures with the isomeric dyestuffs of the formula ##STR2## wherein R represents methyl or ethyl andX.sup.- represents a colorless anion, are suitable for dyeing polyacrylonitrile and, in particular, polyacrylonitrile-wool mixtures.
    Type: Grant
    Filed: April 4, 1988
    Date of Patent: June 20, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventor: Alfred Brack
  • Patent number: 4818815
    Abstract: The invention relates to novel 1,2,3-thiadiazole-axo compounds of formula ##STR1## wherein R is unsubstituted or substituted alkyl or alkenyl,R.sub.1 is hydrogen or unsubstituted or substituted alkyl or alkenyl,R.sub.2 is hydrogen or unsubstituted or substituted alkyl, alkenyl, cycloalkyl or phenyl, orR.sub.1 and R.sub.2, together with the nitrogen atom to which they are attached, are a 5- or 6-membered heterocyclic ring which may contain one or two additional hetero atoms as ring members and/or may be substituted, or R.sub.1 together with R.sub.3 ortho to the amino group form a partially hydrogenated, unsubstituted or substituted 5-or 6-membered heterocyclic ring which may contain an additional N or O atom as ring member,R.sub.3 and R.sub.4 are each independently of the other hydrogen, alkyl, alkoxy, alkanoylamino or halogen,R.sub.5 is hydrogen or together with R.sub.4 in ortho-position forms the member which completes a fused benzene ring,R.sub.7 is hydrogen, optionally substituted phenyl or alkyl, andX.
    Type: Grant
    Filed: July 17, 1986
    Date of Patent: April 4, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Moser
  • Patent number: 4754022
    Abstract: The invention relates to novel cationic isothiazolazo compounds of the formula ##STR1## wherein R.sub.1 is unsubstituted or substituted C.sub.1 -C.sub.4 alkylR.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl,R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, cyano, C.sub.1 -C.sub.4 alkoxy or by phenyl which is in turn unsubstituted or substituted by methyl, methoxy and/or halogen,R.sub.5 and R.sub.6 are each independently of the other hydrogen or C.sub.1 -C.sub.4 alkylR.sub.7 is hydrogen, C.sub.1 -C.sub.4 alkyl or phenyl,Y is the direct bond or the group ##STR2## wherein R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.8 and R.sub.9 are each hydrogen and, if Y is the direct bond, they are each independently of the other hydrogen or C.sub.1 -C.sub.4 alkyl, andX.sup..crclbar. is an anion. These compounds can be used as dyes for dyeing or printing in particular polyacrylonitrile materials in blue shades.
    Type: Grant
    Filed: October 24, 1985
    Date of Patent: June 28, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Moser
  • Patent number: 4687842
    Abstract: Compounds of the formula ##STR1## wherein each of R and R.sub.1 is independently hydrogen, C.sub.1-4 alkyl, phenyl or phenyl substituted by 1 to 3 C.sub.1-4 alkyl, C.sub.1-4 alkoxy or halo substitutents orR and R.sub.1 taken together are trimethylene or tetramethylene,each of R.sub.2 and R.sub.3 is independently allyl, C.sub.1-4 alkyl, phenyl (C.sub.1-4 alkyl) or C.sub.2-4 alkyl monosubstituted by hydroxy, cyano or carbamoyl, ##STR2## wherein R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are as defined in the specification, andA.sup..crclbar. is an anion, and mixtures thereof with cationic 5-hydroxypyrazole dyes, are useful for dyeing and printing materials dyeable with basic dyes, e.g., homopolymers and copolymers of acrylonitrile and asymmetrical dicyanoethylene, polyamides and polyesters modified to contain acidic groups, leather and paper.
    Type: Grant
    Filed: January 14, 1980
    Date of Patent: August 18, 1987
    Assignee: Sandoz Ltd.
    Inventor: Beat Henzi
  • Patent number: 4638053
    Abstract: Chlorozincate salts of benzothiazonium azo compounds are prepared by reacting benzothiazolium azo compounds with an dialkylsulfate having from 1 to 4 carbon atoms in the alkyl radicals, which process comprises carrying out the reaction in an aqueous medium at a temperature of from 10.degree. to 80.degree. C. in the presence of an acid acceptor and the alkylation with the use of from 1.8 to 2.5 mols of the dialkylsulfate, calculated on the starting azo dyestuff, at a pH not exceeding 7. The prepared benzothiazolium azo compound is precipitated as chlorozincate salt, especially with the use of an alkali metal chloride. According to this process, the chlorozincate salts are obtained in higher purity. A perceptible decomposition of the benzothiazolium azo compound does not occur. Chemicals, for example the alkylation agent and acid-binding agents need be used in a small quantity.
    Type: Grant
    Filed: September 11, 1985
    Date of Patent: January 20, 1987
    Assignee: Hoechstaktiengesellschaft
    Inventors: Rudolf Neeb, Reinhard Mohr
  • 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: 4500715
    Abstract: 1,3,4-Thiazole derivatives of the formula ##STR1## wherein R.sub.26 ' denotes a C.sub.1 -C.sub.8 -alkyl radical which is optionally substituted by hydroxyl, halogen, cyano, C.sub.1 -C.sub.4 -alkoxy, carboxyl, aminocarbonyl or C.sub.1 -C.sub.4 -alkoxycarbonyl, a C.sub.2 -C.sub.4 -alkenyl radical, a cyclohexyl radical which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, a phenyl, benzyl or phenylethyl radical which is optionally substituted by halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, a C.sub.1 -C.sub.2 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, mono- or di-C.sub.1 -C.sub.4 -alkylaminocarbonyl, aminocarbonyl, mono- or di-C.sub.1 -C.sub.4 -alkylaminosulphonyl, 2-thienyl, 2-furyl, 2-tetrahydrofuryl, amino, C.sub.1 -C.sub.4 -alkylamino or di-(C.sub.1 -C.sub.4 -alkyl)-amino radical or a phenylamino or benzylamino radical which is optionally substituted by C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy and R.sub.27 ' denotes a C.sub.1 -C.sub.
    Type: Grant
    Filed: January 26, 1981
    Date of Patent: February 19, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hauke Furstenwerth