Plural Azo Groups In The Same Azo Moiety Attached Indirectly To Each Other By Nonionic Bonding Patents (Class 534/608)
  • 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: 20110023242
    Abstract: The invention relates to the dyeing of keratin materials using dichromophore dyes with a carbonyl or heterocyclic linker. The invention relates to a dye composition comprising a dye with a carbonyl or heterocyclic linker, and to a dyeing process with a lightening effect on keratin materials, in particular keratin fibers, especially human keratin fibers such as the hair, using said composition, optionally in the presence of a cosmetically acceptable acid or base. It similarly relates to novel dyes and to the uses thereof in lightening keratin materials. This composition makes it possible to obtain a coloring with a lightening effect which is particularly resistant and visible on dark keratin fibers.
    Type: Application
    Filed: September 23, 2008
    Publication date: February 3, 2011
    Inventor: Andrew Greaves
  • Patent number: 7824451
    Abstract: The present invention provides a blue dye mixture which contains the pigments represented by formulae [1], [2], [3], and [4] The present invention also relates to dye mixtures in which there are compounded therewith a yellow dye mixture and/or a red dye mixture. The invention further relates to a method of dyeing polyester-based fibers and dyed polyester-based fibers and dyed polyester-based fiber materials.
    Type: Grant
    Filed: June 29, 2004
    Date of Patent: November 2, 2010
    Assignee: DyStar Textilfarben GmbH & Co. Deutschland KG
    Inventors: Toshio Hihara, Wataru Seto, Koichi Fujisaki, Daisuke Hosoda, Hiroshi Inoue
  • Publication number: 20100263139
    Abstract: The present invention relates to thiol/disulphide azo quinolinium compounds for dyeing keratin fibres. The invention relates to a dye composition comprising a particular thiol/disulphide azo quinolinium chromophore-containing thiol or disulphide dye, and to a process for dyeing keratin fibres such as the hair, using said composition. It similarly relates to novel particular thiol/disulphide azo quinolinium chromophore-containing dyes and to the uses thereof in dyeing keratin fibres. The dyeing process according to the invention makes it possible to dye keratin fibres without damaging them, in a manner which is particularly persistent with respect to shampooing operations and common attacks. Moreover, the novel dyes according to the invention extend the colour range to violets and blues. This process also makes it possible to dye bleached keratin fibres in a strong and chromatic manner.
    Type: Application
    Filed: September 8, 2008
    Publication date: October 21, 2010
    Inventors: Nicolas Daubresse, Andrew Greaves
  • Publication number: 20080295260
    Abstract: Formula (I) wherein R1 and R2 each independently from each other are a residue of an organic dye: Y1 and Y2 each independently from each other are unsubstituted or substituted, straightchain or branched, interrupted or uninterrupted —C1-C10alkylene-; —C5-C10cycloalkylene-; C5-C10arylene; or —C5-C10arylene-(C1C10alkylene)-; Z1 and Z2 independently from each other are Formula (II) are each independently from each other hydrogen; or unsubstituted or substituted, straight-chain or branched, monocyclic or polycyclic, interrupted or uninterrupted C1-C14alkyl; C2-C14alkenyl; C6-C10aryl; C6-C10aryl-C1-C10alkyl; or C5-C10alkyl(C5-C10aryl); r, q and n independently from each other are 0 or 1, if n is 0, Z3 is hydrogen; and if n is 1, Z3 is —S—; with the proviso that the method does not comprise treating the fiber with an enzyme of the type of a protein disulfidisomerase (EC 5.3.4.1).
    Type: Application
    Filed: March 29, 2005
    Publication date: December 4, 2008
    Inventors: Victor Paul Eliu, Beate Frohling, Dominique Kauffmann
  • Publication number: 20080196175
    Abstract: The present invention concerns a new dissymmetrical cationic polyazo compounds of formula (I) Dye1-L-Dye2. The present invention also relates to dye compositions comprising such compounds as direct dye in a medium that is suitable for dyeing keratin fibres, and also to a process for dyeing keratin fibres using this composition and a multi-compartment device. The present invention provides direct dyes with which strong and varied shades that are resistant to external attacking factors such as bad weather and shampooing, for which there is no observation of any problem of change in colour over time.
    Type: Application
    Filed: November 24, 2005
    Publication date: August 21, 2008
    Inventors: Andrew Greaves, Herve David
  • Patent number: 7396368
    Abstract: Disclosed herein are symmetrical cationic diazo compounds chosen from compounds of formula (I), their resonance forms, their acid addition salts, and their solvates: Also disclosed herein are dyeing compositions comprising such compounds as a direct dye in a medium appropriate for the dyeing of keratin fibers, a method of coloring keratin fibers comprising contacting the keratin fibers with such compositions, and a device comprising a plurality of compartments.
    Type: Grant
    Filed: December 15, 2005
    Date of Patent: July 8, 2008
    Assignee: L'Oreal S.A.
    Inventors: Hervé David, Andrew Greaves, Nicolas Daubresse
  • 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: 7351267
    Abstract: The present disclosure relates to symmetrical cationic diazo compounds of formula (I) below, their resonance forms, and also their acid addition salts and their solvates: wherein W1 radicals, which are identical, are chosen from a halogen atom, or an —NR4-Ph-NR5R6, —NR4-Ph-OR7, —O-Ph-OR7 or —O-Ph-NR5R6 group or else an —NR5R6 or —OR7 group with certain provisos; L, a non-cationic linker connecting the two identical azo chromophores, is chosen from a covalent bond; an optionally substituted C1-C40 alkyl radical optionally interrupted by a (hetero)cycle, the alkyl radical being optionally interrupted by at least one heteroatom or group comprising at least one heteroatom or an optionally substituted phenyl radical. The disclosure further relates to dyeing compositions comprising such compounds as a direct dye in a medium appropriate for the dyeing of keratin fibers, and also to a method of coloring keratin fibers that employs this composition, and a device comprising a plurality of compartments.
    Type: Grant
    Filed: December 15, 2005
    Date of Patent: April 1, 2008
    Assignee: L'Oreal S.A.
    Inventors: Hervé David, Andrew Greaves, Nicolas Daubresse
  • 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: 7288639
    Abstract: The present disclosure relates to dissymmetrical cationic diazo compounds having at least one 4-pyridinium unit and a cationic or non-cationic linker. The disclosure further relates to dyeing compositions comprising these compounds as a direct dye in a medium appropriate for the dyeing of keratin fibers. Further, the disclosure relates to a method of coloring keratin fibers that employs this composition, and a device having a plurality of compartments.
    Type: Grant
    Filed: December 15, 2005
    Date of Patent: October 30, 2007
    Assignee: L'Oreal S.A.
    Inventors: Hervé David, Andrew Greaves, Nicolas Daubresse
  • Patent number: 7288122
    Abstract: The present disclosure relates to cationic diazo dye compounds of formula (I): Dye1-LK-Dye2, ??(I) dye compositions comprising the direct dye compounds, and also to a process for dyeing keratin fibers using this composition and a multi-compartment kit.
    Type: Grant
    Filed: June 23, 2005
    Date of Patent: October 30, 2007
    Assignee: L'Oreal S.A.
    Inventors: Andrew Greaves, Hervé David
  • Patent number: 7285138
    Abstract: The present disclosure relates to a cationic diazo compound of formula (I): Dye1-LK-Dye2 wherein Dye1 and Dye2 are such that the compound of formula (I) is not symmetrical, and are chosen from: The disclosure also relates to dye compositions comprising compounds of formula (I) as direct dye, and further relates to a process for dyeing keratin fibers using the compositions disclosed herein and also to a multi-compartment device.
    Type: Grant
    Filed: June 23, 2005
    Date of Patent: October 23, 2007
    Assignee: L'Oreal, S.A.
    Inventors: Andrew Greaves, Hervé David
  • Patent number: 7282069
    Abstract: The present disclosure relates to cationic diazo compounds chosen from those of formula (I) and the acid addition salts thereof: Dye1-LK-Dye2 (I); and to dye compositions comprising the the compounds as direct dye, and also to a process for dyeing keratin fibers using this composition and a multi-compartment device.
    Type: Grant
    Filed: June 23, 2005
    Date of Patent: October 16, 2007
    Assignee: L'Oreal S.A.
    Inventors: Andrew Greaves, Hervé David
  • Patent number: 7261743
    Abstract: The present disclosure relates to the process of dyeing human keratinous fibers, such as the hair, with at least one specific direct dye in cosmetic compositions. Also disclosed herein are the direct dyeing and lightening compositions comprising said compounds, and the corresponding dyeing kits.
    Type: Grant
    Filed: June 7, 2002
    Date of Patent: August 28, 2007
    Assignee: L'Oreal
    Inventors: Grégory Plos, Henri Samain
  • Patent number: 7247713
    Abstract: The present disclosure relates to symmetrical cationic diazo compounds of formula (I), the resonance forms, and also the acid addition salts and/or the solvates thereof: The present disclosure further relates to dyeing compositions comprising such compounds as a direct dye in a medium appropriate for the dyeing of keratin fibers, and also to a method of coloring keratin fibers that employs this composition, and a multi-compartment kit containing such compositions.
    Type: Grant
    Filed: December 15, 2005
    Date of Patent: July 24, 2007
    Assignee: L'Oreal, S.A.
    Inventors: Hervé David, Andrew Greaves, Nicolas Daubresse
  • Patent number: 7208586
    Abstract: Disclosed are cationic diazo compounds of the following formula Dye1-LK-Dye2??(I) in which Dye1 and Dye2 represent: Also herein disclosed are dye compositions comprising the cationic diazo compounds as direct dye, a process for dyeing keratin fibers using this composition, and a multi-compartment device.
    Type: Grant
    Filed: June 23, 2005
    Date of Patent: April 24, 2007
    Assignee: L'Oreal S.A.
    Inventors: Andrew Greaves, Hervé David
  • Patent number: 7189266
    Abstract: The present disclosure relates to a composition for dyeing human keratin fibers, such as the hair, comprising, in a medium suitable for dyeing, at least one direct dye and at least on dicationic compound. Also disclosed herein is a process for dyeing and lightening human keratin fibers, such as the hair, with the compositions disclosed, as well as a the corresponding dyeing kits.
    Type: Grant
    Filed: June 10, 2002
    Date of Patent: March 13, 2007
    Assignee: L'Oreal, S.A.
    Inventors: Grégory Plos, Henri Samain
  • Patent number: 7172633
    Abstract: The present invention relates to a lightening dye composition comprising, in a suitable dyeing medium, an oxidizing agent, an alkaline agent in an amount such that the pH of the composition is greater than 7, and a mixed cationic dye comprising several chromophores linked together via a linker, at least two of the chromophores being different, the chromophores having an absorbance of between 400 and 800 nm. The invention makes it possible to obtain particularly fast colorations.
    Type: Grant
    Filed: June 16, 2004
    Date of Patent: February 6, 2007
    Assignee: L'Oréal S.A.
    Inventors: Henri Samain, Leila Hercouet
  • Patent number: 7172631
    Abstract: The present disclosure relates to a dyeing composition for human keratinous fibers, such as the hair, comprising, in a suitable dyeing medium, at least one oxidation dye, and at least one dicationic compound. The disclosure further relates to the dyeing methods and dyeing kit using the dye composition.
    Type: Grant
    Filed: June 7, 2002
    Date of Patent: February 6, 2007
    Assignee: L'Oreal S.A.
    Inventors: Grégory Plos, Henri Samain
  • 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: 7166710
    Abstract: The present invention relates to novel cationic dye of formula (1) and (1a) wherein A is an organic radical of formula (2) or (3) wherein R1 and R2 are each independently of the other unsubstituted or substituted C1–C14alkyl or an aryl radical, R3 is hydrogen, unsubstituted or substituted C1–C14alkyl, unsubstituted or substituted C1–C14alkoxy, cyan or halogenid, R4 is hydrogen, unsubstituted or substituted C1–C14alkyl or an aryl radical, 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, paper, cellulose or polyamides, and preferably human hair.
    Type: Grant
    Filed: March 16, 2004
    Date of Patent: January 23, 2007
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Victor Paul Eliu, Beate Fröhling
  • Patent number: 7153384
    Abstract: Laser ray transmitting colored thermoplastic resin composition containing a dis-azo salt forming dye consisting of an anionic component from a dis-azo acid dye and an organic ammonium component, said acid dye being represented by Formula (1) below, R1—N?N-E-N?N—R2; ??(1) E: (2), (3), (4); R1, R2: aryl, pyrazolone; one or more of E, R1, R2 have sulfonic acid group, R3, R4: hydrogen atom, alkyl, sulfonic acid group, R5, R6: hydrogen atom, sulfonic acid group, R15: sulfonic acid group. Method of laser welding wherein a contact portion of a laser ray transmitting material comprising the laser ray transmitting colored thermoplastic resin composition above and a laser ray absorbing material is welded by irradiating laser ray so that the laser ray passes through the laser ray transmitting material and is absorbed in the laser ray absorbing material with the laser ray transmitting material and the laser ray absorbing material in contact with each other.
    Type: Grant
    Filed: November 5, 2003
    Date of Patent: December 26, 2006
    Assignee: Orient Chemical Industries, Ltd.
    Inventors: Shuji Sugawara, Yoshiteru Hatase
  • 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: 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: 6346609
    Abstract: Cationic azo dyes of the general formula I where R1, R2, R3, A1, A2, B1, B2, An⊖, n and K have the meaning given in the specification are prepared and used for the dyeing and printing of natural or synthetic substrates and mixtures thereof.
    Type: Grant
    Filed: May 4, 2001
    Date of Patent: February 12, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Karl-Heinz Etzbach, Torsten Freund, Rainer Tresch
  • 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: 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: 5824118
    Abstract: A dye which is durable for practical use in the field of coloring automobile seat materials for which a good light-fastness is required and a dyeing method making use of the dye is provided. In the method, a disazo dye is obtained by converting guanazole to a tetrazo compound and coupling the tetrazo with an indole derivative to form a compound which is then quaternized using e.g., an alkylating agent resulting in a red dye with superior light-fastness at high temperatures.
    Type: Grant
    Filed: September 8, 1995
    Date of Patent: October 20, 1998
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Minoru Akai, Itsuo Suda, Katsumi Nonomura, Kumiko Arai
  • Patent number: 5708151
    Abstract: The cationic imidazole azo dyes of the formulae ##STR1## in which A and A.sub.1 independently of one another are each a radical of the formula ##STR2## Z is the radical of an aliphatic or aromatic diamine, R.sub.1 and R.sub.2 are each hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl or, together with the two nitrogen atoms to which they are attached and with Z, form a 5-, 6- or 7-membered ring, X is the radical of a bridging member, n is 2, 3 or 4, Z.sub.1 is the radical of an aromatic diamine, Z.sub.2 is the radical of an aliphatic diamine, KK is the radical of a coupling component, R.sub.3 and R.sub.4 are each hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl, R.sub.5 and R.sub.6 independently of one another are each hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy and An.sup..crclbar. is a colorless anion, are particularly suitable for the dyeing of paper in red or violet shades having good fastness properties.
    Type: Grant
    Filed: November 2, 1995
    Date of Patent: January 13, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventor: Peter Mockli
  • 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: 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: 5037964
    Abstract: (i) Metal-free compounds of the formula ##STR1## These compounds are useful as dyes for paper and textiles.
    Type: Grant
    Filed: October 17, 1986
    Date of Patent: August 6, 1991
    Assignee: Sandoz Ltd.
    Inventors: Helmut A. Moser, Roland Wald
  • 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: 4833235
    Abstract: Disazo compounds of the formula ##STR1## and salt thereof, D is the radical of a diazo component of the benzene or naphthalene series.K is the radical of a heterocyclic coupling component of the aminopyrazole-, pyridone- or barbituric acid-series, n is 1 to 4,R.sub.1 is hydrogen, C.sub.1-4 alkyl or substituted C.sub.1-4 alkyl,each of R.sub.2 and R.sub.3 is independently hydrogen, halo, C.sub.1-4 alkyl, substituted C.sub.1-4 alkyl, C.sub.1-4 alkoxy, substituted C.sub.1-4 alkoxy, --NHCO--Rhd 5, amino, substituted amino or a quaternary ammonium group, wherein R.sub.5 is C.sub.1-4 alkyl, substituted C.sub.1-4 alkyl, C.sub.1-4 alkoxy or amino,R.sub.4 is hydrogen, C.sub.1-4 alkyl, C.sub.
    Type: Grant
    Filed: October 7, 1987
    Date of Patent: May 23, 1989
    Assignee: Sandoz Ltd.
    Inventor: Reinhard Pedrazzi
  • Patent number: 4686285
    Abstract: (i) Metal-free compounds of the formula ##STR1## (ii) tautomers thereof, (iii) 1:1 and 1:2 metal complexes of (i) and (ii),(iv) salts of (i), (ii), and (iii), and(v) mixtures of (i), (ii), (iii), and (iv),wherein the symbols are as defined in the Specification, are useful as dyes for, for example, polymers and copolymers of acrylonitrile, polyesters modified to contain acid groups, polyamides such as wool, leather, cotton, bast fibers such as hemp, flax, sisal jute, coir and straw, regenerated cellulose, glass fibers and paper (those wherein R.sub.o is other than hydrogen) or as intermediates for the synthesis of dyes.
    Type: Grant
    Filed: February 8, 1985
    Date of Patent: August 11, 1987
    Assignee: Sandoz Ltd.
    Inventor: Reinhard Pedrazzi
  • Patent number: 4675388
    Abstract: Polymers comprising two the more recurring units of formula ##STR1## wherein A.sub.1 is an aromatic bridging groupeach K.sub.1 is independently the radical of a coupling component,E is an aliphatic, aromatic or aromatic heterocyclic bridging radical,each R.sub.1 and R.sub.2 is independently C.sub.1-4 alkyl substituted C.sub.1-4 alkyl, C.sub.3-6 alkenyl or substituted C.sub.3-6 alkenyl orboth R.sub.1 's together with the nitrogen atom to which they are attached and/or both R.sub.2 3 s together with the nitrogen atom to which they are attached form a morpholinium, piperidinium or pyrrolidinium group, andeach A.sup..crclbar. is independently a non-chromophoric anion, are useful as dyes, particularly for dyeing paper and leather.
    Type: Grant
    Filed: November 13, 1984
    Date of Patent: June 23, 1987
    Assignee: Sandoz Ltd.
    Inventors: Manfred Greve, Emil J. Moriconi, Helmut Moser
  • Patent number: 4665162
    Abstract: Metal-free azo compounds of the formula ##STR1## wherein Ra is an aromatic group or an active methylene coupling component radical as defined in the specification,R.sub.t is an arylazo group or a group of the formula --Y--Z,whereinY is a direct bond or a bridging radical, andZ is a basic amino or quaternary ammonium group, ##STR2## wherein each of the variables is as defined above or below, x is a direct bond or a bridging radical,x is hydrogen, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, amino or carboxy,ring B is further unsubstituted or further substituted,d is 0, 1 or 2, andn is 0 or 1,with the provisos that (i) the compounds contain an average of at least 1.3 basic water-solubilizing groups, and (ii) the compounds are free of sulfo groups, and 1:1 and 1:2 metal complexes thereof, which metal-free compounds and metal complexes are useful as dyes for leather and paper.
    Type: Grant
    Filed: June 18, 1985
    Date of Patent: May 12, 1987
    Assignee: Sandoz Ltd.
    Inventors: Paul Doswald, Emil Moriconi, Helmut Moser, Horst Schmid
  • Patent number: 4634764
    Abstract: Compounds of the formula ##STR1## wherein each R is independently --N(R.sub.1).sub.2, --N.sup..sym. (R.sub.2).sub.3 A.sup..crclbar. or hydroxy, whereineach R.sub.1 is independently hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl or aryl orboth R.sub.1 's taken together and with the nitrogen atom to which they are attached form a 5- or 6-membered saturated heterocyclic ring,each R.sub.2 is independently alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl or aryl ortwo R.sub.2 's taken together and with the nitrogen atom to which they are attached form a 5- or 6-membered saturated heterocyclic ring orall three R.sub.2 's taken together and with the nitrogen atom to which they are attached form a 5- or 6-membered unsaturated heterocyclic ring, andA.sup..crclbar. is a non-chromophoric anion,each T is independently a bridging radical, andZ is hydrogen or --N.dbd.
    Type: Grant
    Filed: November 10, 1983
    Date of Patent: January 6, 1987
    Assignee: Sandoz Ltd.
    Inventor: Manfred Greve
  • Patent number: 4591635
    Abstract: Metal-free compounds and 1:1 and 1:2 metal complexes of the formula ##STR1## or a 1:2 metal complex of a metal-free compound of said formula and a metallizable azo compound not of said formula, whereineach K is independently a coupling component radical of the pyrazolone-5, 5-aminopyrazole, pyridone, 2,6-diaminopyridine, .beta.-naphthol, acetic acid ester, acetic acid amide or N-substituted N,N-disubstituted aniline series,each K.sub.1 is independently ##STR2## wherein R.sub.3 is hydrogen, C.sub.1-4 alkyl, phenyl or benzyl,R.sub.4 is C.sub.1-4 alkyl, (C.sub.1-4 alkoxy)-carbonyl or --CO--N(R.sub.8).sub.2, wherein each R.sub.8 is independently hydrogen or C.sub.1-4 alkyl,R.sub.5 is amino or hydroxy,R.sub.5a is hydroxy,T is hydrogen, cyano, ##STR3## or (C.sub.1-4 alkyl)carbonyl, wherein R.sub.7, R.sub.10, R.sub.12, Z.sub.a and A.crclbar. are as defined in the specification,each R.sub.1 is independently hydrogen, halo, hydroxy, C.sub.1-4 alkoxy or C.sub.1-4 alkyl, orR.sub.1 and R.sub.
    Type: Grant
    Filed: November 10, 1983
    Date of Patent: May 27, 1986
    Assignee: Sandoz Ltd.
    Inventors: Manfred Greve, Helmut Moser
  • Patent number: 4587292
    Abstract: Metal-free azo compounds of the formula ##STR1## wherein Ra is an aromatic group or an active methylene coupling component radical as defined in the specification,R.sub.t is an arylazo group or a group of the formula --Y--Z, whereinY is a direct bond or a bridging radical, andZ is a basic amino or quaternary ammonium group,R is ##STR2## wherein each of the variables is as defined above or below, X is a direct bond or a bridging radical,x is hydrogen, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, amino or carboxy,ring B is further unsubstituted or further substituted,d is 0, 1 or 2, andn is 0 or 1,with the provisos that (i) the compounds contain an average of at least 1.3 basic water-solubilizing groups, and (ii) the compounds are free of sulfo groups, and 1:1 and 1:2 metal complexes thereof, which metal-free compounds and metal complexes are useful as dyes for leather and paper.
    Type: Grant
    Filed: August 18, 1982
    Date of Patent: May 6, 1986
    Assignee: Sandoz Ltd.
    Inventors: Paul Doswald, Emil Moriconi, Helmut Moser, Horst Schmid
  • Patent number: 4581445
    Abstract: There are described novel cationic benzothiazole disazo compounds of the formula ##STR1## K independently of one another are each a coupling component, R independently of one another are each an unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl group,R.sub.1 independently of one another are each hydrogen, unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted C.sub.1 -C.sub.4 -alkoxy, or halogen,X is the direct bond, --(CH.sub.2).sub.y wherein y is a number from 1 to 4, --CH.dbd.CH--, a phenylene group, a naphthylene group, a heterocyclic radical, an --NH-alkylene-(C.sub.1 -C.sub.6)--NH-- radical or an --NH-arylene-NH-- radical, andAn is an anion, with the proviso that when the coupling component K is a dimethylaminophenyl radical, the divalent bridge member X is not the --(CH.sub.2).sub.2 -- group are useful for dyeing and printing textile materials, leather and in particular paper. The dyeings obtained have good fastness properties, especially good fastness on paper to light.
    Type: Grant
    Filed: September 16, 1983
    Date of Patent: April 8, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Visvanathan Ramanathan
  • Patent number: 4562247
    Abstract: There are described azo compounds of the formula ##STR1## wherein D.sub.1 and D.sub.2 are each the radical of a diazo component, R is C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 alkyl substituted by C.sub.1 -C.sub.4 -alkoxy or halogen or is phenyl or phenyl substituted by C.sub.1 -C.sub.4 -alkyl, halogen or C.sub.1 -C.sub.4 alkoxy, and Y is a basic or cationic group. These azo compounds can be used as dyes for dyeing and printing natural and synthetic, cationically dyeing substrates, particularly textile materials and paper.
    Type: Grant
    Filed: May 29, 1984
    Date of Patent: December 31, 1985
    Assignee: Ciba Geigy Corporation
    Inventor: Visvanathan Ramanathan
  • Patent number: 4517358
    Abstract: Cationic disazo compounds of the formula ##STR1## wherein K independently of one another are each a coupling component,R independently of one another are each an unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl group,R.sub.1 independently of one another are each hydrogen, unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted C.sub.1 -C.sub.4 -alkoxy, or halogen, andAn is an anionare useful as dyes, in particular as paper dyes, whereby dyeings fast to water are obtained. The dyeings obtained have very good fastness to light and to wet processing.Disazo compounds of the formula ##STR2## wherein K and R, are as defined above are useful as disperse dyes and as intermediates in the preparation of the above cationic disazo compounds.
    Type: Grant
    Filed: September 14, 1982
    Date of Patent: May 14, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Visvanathan Ramanathan