Acyclic Nitrogen Is Bonded Directly To A -c(=x)- Group, Wherein X Is Chalcogen Patents (Class 544/77)
  • Patent number: 7905928
    Abstract: Reactive dyes of the formula (1) in which Q1, X, V1, V2, B, T and R1, R2, R4 and R5 are defined in the claims and in the disclosure and wherein the reactive dyes are suitable for dyeing widely varying fiber materials, in particular cellulosic fiber materials and produce dyeings with good allround properties.
    Type: Grant
    Filed: October 7, 2008
    Date of Patent: March 15, 2011
    Assignee: Huntsman International LLC
    Inventors: Athanassios Tzikas, Thomas Verdugo, Georg Roentgen
  • Publication number: 20100251490
    Abstract: Reactive dyes of the formula (1) in which Q1 is hydrogen, halogen or a radical of the formula R1, R2 and R3 independently of one another are hydrogen or C1-C4alkyl which is unsubstituted or substituted by hydroxyl, sulfo, carboxyl or sulfato, and R1 in formula (1) and R1 in formula (2a) have identical or different meanings and R2 in formula (1) and R2 in formula (2a) have identical or different meanings, (R4)0-1 and (R5)0-1 independently of one another are 0 or 1 identical or different substituents from the group consisting of C1-C4alkyl, C1-C4alkoxy, halogen and sulfo, A is hydrogen or C1-C4alkyl which is unsubstituted or substituted by hydroxyl, sulfo, carboxyl or sulfato, phenyl which is unsubstituted or substituted by C1-C4alkyl, C1-C4alkoxy, C2-C4alkanoylamino, hydroxyl, carboxyl, carbamoyl, sulfo or halogen, phenyl-C1-C2alkylene which is unsubstituted or substituted in the phenyl ring by C1-C4alkyl, C1-C4alkoxy, C2-C4alkanoylamino, hydroxyl, carboxyl, sulfo, carbamoyl or halogen, or C5-
    Type: Application
    Filed: October 7, 2008
    Publication date: October 7, 2010
    Applicant: Huntsman International LLC
    Inventors: Athanassios Tzikas, Thomas Verdugo, Georg Roentgen
  • Patent number: 6355783
    Abstract: The invention relates to novel soluble pigment precursors possessing not only higher thermal stability but also improved solubility characteristics and to a process for mass coloration of high temperature polymers that utilizes these novel soluble pigment precursors. The pigment precursors of the invention are essentially of the formula A(B)x  (I) where x is an integer from 1 to 8, A is the radical of a chromophore of the quinacridone, anthraquinone, perylene, indigo, quinophthalone, indanthrone, isoindolinone, isoindoline, dioxazine, azo, phthalocyanine or diketopyrrolopyrrole series, this radical being linked with xB groups via one or more heteroatoms, these heteroatoms being selected from the group consisting of N, O and S and forming part of the radical A, and B is hydrogen or a group of the formula although at least one B group is not hydrogen and when x is from 2 to 8 the B groups may be identical or different.
    Type: Grant
    Filed: September 7, 2000
    Date of Patent: March 12, 2002
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Leonhard Feiler, Zhimin Hao
  • Patent number: 6319289
    Abstract: Compounds of formula (I) wherein A is hydrogen or a descretionary radical, a novel process for their preparation and their use for the dyeing of organic substrates.
    Type: Grant
    Filed: March 31, 1999
    Date of Patent: November 20, 2001
    Assignee: Clariant Finance (BVI) Limited
    Inventor: Georg Schöfberger
  • Publication number: 20010031864
    Abstract: The invention relates to a process for preparing triphendioxazine compounds by cyclizing the intermediates (IV) 1
    Type: Application
    Filed: March 6, 2001
    Publication date: October 18, 2001
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Bansi Lal Kaul, Bruno Piastra, Pascal Steffanut
  • Patent number: 6302923
    Abstract: Compounds of formula (I) with the meanings of R1, R1′, R2, R2′, X, X′, Y, Y′, m and n as given in claim 1 can be used as paper dyes or direct dyes or for the preparation of ink-jet inks.
    Type: Grant
    Filed: May 19, 2000
    Date of Patent: October 16, 2001
    Assignee: Clariant Finance (BVI) Limited
    Inventor: Ludwig Hasemann
  • Patent number: 6281339
    Abstract: Monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan or dioxazine dyes comprising at least one structural unit of formula (1) wherein Z is C1-C24alkoxy unsubstituted or substituted in the alkyl moiety, or uninterrupted or interrupted in the alkyl moiety by oxygen; phenoxy unsubstituted or substituted in the phenyl ring; C1-C4alkylthio unsubstituted or substituted in the alkyl moiety; phenylthio unsubstituted or substituted in the phenyl ring; amino; N-mono- or N,N-di-C1-C24-alkylamino, unsubstituted or substituted in the alkyl moiety, or uninterrupted or interrupted in the alkyl moiety by oxygen or by a radical —NR1— in which R1 is hydrogen or C1-C4alkyl; C10-C20terpeneamino; C5-C7cycloalkylamino unsubstituted or substituted in the cycloalkyl ring; phenyl- or naphthyl-amino or N—C1-C4alkyl-N-phenyl- or N—C1-C4alkyl-N-naphthyl-amino, each unsubstituted or substituted in the aryl moiety; morpholino; piperazin-1-yl or piperidin-1-yl, and X is hyd
    Type: Grant
    Filed: September 13, 2000
    Date of Patent: August 28, 2001
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Urs Lehmann, Marcel Frick
  • Patent number: 6274728
    Abstract: Compounds of formula A(B)x  (I), wherein x is an integer from 1 to 8, A is the radical of a chromophore of the quinacridone, anthraquinone, perylene, indigo, quinophthalone, indanthrone, isoindolinone, isoindoline, dioxazine, azo, phthalocyanine or diketopyrrolopyrrole series that is bonded to x groups B via one or more hetero atoms, those hetero atoms being selected from the group consisting of N, O and S and forming part of the radical A, each group B independently of any other(s) is hydrogen or a group of the formula  at least one group B being a group of the formula The compounds according to the invention are used in high-molecular-weight organic materials, thermo-, photo- or chemo-sensitive recording materials, light-sensitive negative or positive resist compositions, ink compositions for ink-jet printing and color tapes for thermal transfer printing.
    Type: Grant
    Filed: December 16, 1999
    Date of Patent: August 14, 2001
    Assignee: Ciba Specialty Chemicals Corp.
    Inventors: Véronique Hall-Goulle, Aline Bize
  • Patent number: 6159250
    Abstract: Doubled reactive dyes of the general formula I ##STR1## where Chr is a chromophore residue with or without further fiber-reactive groups and derived from a metallized or unmetallized mono- or disazo dye, from a triphendioxazine, from an anthraquinone, from a metallized formazan or from a metallized phthalocyanine,Z.sup.1, Z.sup.2 and Z.sup.3 are each independently of the others hydrogen or substituted or unsubstituted C.sub.1 -C.sub.6 -alkyl,Hal is fluorine or chlorineL.sup.1 and L.sup.2 are each independently of the other C.sub.2 -C.sub.6 -alkylene with or without interruption by 1 or 2 unadjacent oxygen atoms, andA is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.6 -alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted C.sub.2 -C.sub.3 -alkenyl, substituted or unsubstituted C.sub.1 -C.sub.6 -alkoxy, substituted or unsubstituted phenoxy or C.sub.1 -C.sub.6 -alkylamino,and their mixtures are prepared and useful for dyeing or printing hydroxyl-containing or nitrogenous substances.
    Type: Grant
    Filed: December 22, 1999
    Date of Patent: December 12, 2000
    Assignee: BASF Aktiengesellschaft
    Inventor: Manfred Patsch
  • Patent number: 6136970
    Abstract: An asymmetric dioxazine compound represented by the following formula (I) in the free acid form: ##STR1## wherein A.sub.1 and A.sub.2 independently of one another are each sulfo, halo, alkyl or alkoxy, X.sub.1 and X.sub.2 independently of one another are each hydrogen, halo, alkyl, alkoxy or phenoxy, R.sub.1 is hydrogen or unsubstituted or substituted alkyl, R.sub.2 and R.sub.3 independently of one another are each hydrogen, alkyl, alkoxy, halo or unsubstituted or substituted amino, Z is a fiber-reactive group, m and n independently of one another are each 0 or 1, provided that m.noteq.n, and L is 1 or 2. This compound is suitable for dyeing and printing cellulose fiber, natural and synthetic polyamide fibers, polyurethane fiber, leather and the like and mixed yarns thereof, to obtain dyed or printed products of a color fast to light, wetness and chlorine with superior build-up and level dyeing properties.
    Type: Grant
    Filed: October 29, 1992
    Date of Patent: October 24, 2000
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazufumi Yokogawa, Takahiko Fujisaki, Miyao Takahashi, Shigeru Kawabata, Naoki Harada, Kingo Akahori, Yutaka Kayane, Takashi Omura
  • Patent number: 6013777
    Abstract: Compounds of formulaA(B).sub.x, (I),wherein x is an integer from 1 to 4,A is the radical of a chromophore of the quinacridone, anthraquinone, perylene, indigo, quinophthalone, isoindolinone, isoindoline, dioxazine, phthalocyanine or azo series, which radical contains x N-atoms attached to B, preferably with at least one directly adjacent or conjugated carbonyl group,B is a group of formula ##STR1## and, if x is 2, 3 or 4, may also be one, two or three hydrogen atoms. The symbols Q, R.sub.1, R.sub.2, R.sub.3, R.sub.4, X, Y, Z, m and n, are as defined in claim 1.These carbamate group-containing soluble chromophores are distinguished by outstanding solid state fluorescence in the UV range as well as the by ease with which they can be converted to the corresponding pigments in the substrate in which they are incorporated.
    Type: Grant
    Filed: June 10, 1998
    Date of Patent: January 11, 2000
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Zhimin Hao, John S. Zambounis, Abul Iqbal
  • Patent number: 5977358
    Abstract: An asymmetric dioxazine compound represented, when shown in free acid form, by the general formula (I): ##STR1## wherein T.sub.1 and T.sub.2 represent a hydrogen atom, a chlorine atom, a bromine atom, a lower alkyl group, a phenoxy group or others, A.sub.1 represents an alkyl group, a chlorine atom, a carboxyl group or others, A.sub.2 represents a hydrogen atom, an alkyl group, a chlorine atom, a carboxyl group or others, R represents a hydrogen atom or a lower alkyl group, X and Y represent a halogen atom, a fiber-reactive group or others, respectively, with the proviso that at least one of X and Y is a fiber-reactive group is provided.The compound is suitable for dyeing or printing of a fiber material or the like which has a hydroxy group and/or an amide group, and provides a blue-dyed product with various fastness, including particularly chlorine fastness.
    Type: Grant
    Filed: July 15, 1998
    Date of Patent: November 2, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masato Inoue, Junya Hada, Toshiyuki Araki
  • Patent number: 5962442
    Abstract: The invention concerns the treatment of hyderandrogenic conditions in humans by the formation of a novel mechanism-based irreversible inhibitor of human 5.alpha.-reductase enzymes from 3-oxo-4-azasteroids having a 1,2-double bond and the pyridine-nucleotide cofactor of the 5.alpha.-reductase enzyme, NADPH. Until the present invention, it was not know or predicted that 3-oxo-4-azasteroids having 1,2-double bond would form a complex with NADPH by the mechanism of 5.alpha.-reductase in vivo. The invention further relates to the novel inhibitor-cofactor complex and pharmaceutical compositions containing the complex.
    Type: Grant
    Filed: May 5, 1997
    Date of Patent: October 5, 1999
    Assignee: Merck & Co., INc.
    Inventors: Herb G. Bull, Georgianna S. Harris
  • Patent number: 5944854
    Abstract: According to the invention, a process for the preparation of triphendioxazines systemetrically or asymmetrically amidated on both sides comprises reducing a triphendioxazine chromophore, which is optionally already amidated on one side, to give the leuco form end amidating and re-oxidizing the leuco form. Products amidated on both sides are obtained in this manner with a high yield and product quality. Novel triphendioxazine dyestuffs are furthermore prepared in this manner.
    Type: Grant
    Filed: July 15, 1997
    Date of Patent: August 31, 1999
    Assignee: Dystar Textilfarben GmbH & Co.
    Inventors: Christian Schumacher, Karl-Josef Herd
  • Patent number: 5886160
    Abstract: Compounds of formulaA(B).sub.x, (I),wherein x is an integer from 1 to 4,A is the radical of a chromophore of the quinacridone, anthraquinone, perylene, indigo, quinophthalone, isoindolinone, isoindoline, dioxazine, phthalocyanine or azo series, which radical contains x N-atoms attached to B, preferably with at least one directly adjacent or conjugated carbonyl group,B is a group of formula ##STR1## and, if x is 2, 3 or 4, may also be one, two or three hydrogen atoms. The symbols Q, R.sub.1, R.sub.2, R.sub.3, R.sub.4, X, Y, Z, m and n, are as defined in claim 1.These carbamate group-containing soluble chromophores are distinguished by outstanding solid state fluorescence in the UV range as well as the by ease with which they can be converted to the corresponding pigments in the substrate in which they are incorporated.
    Type: Grant
    Filed: June 12, 1998
    Date of Patent: March 23, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Zhimin Hao, John S. Zambounis, Abul Iqbal
  • Patent number: 5880282
    Abstract: Improved unsymmetric reactive dyestuffs have the following formula ##STR1## wherein Y.sub.1 is a radical of the formula ##STR2## and wherein the other substituents have the meaning given in the description.
    Type: Grant
    Filed: February 6, 1997
    Date of Patent: March 9, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Harms, Stefan Ehrenberg
  • Patent number: 5780627
    Abstract: Compounds of formulaA(B).sub.x, (I),wherein x is an integer from 1 to 4,A is the radical of a chromophore of the quinacridone, anthraquinone, perylene, indigo, quinophthalone, isoindolinone, isoindoline, dioxazine, phthalocyanine or azo series, which radical contains x N-atoms attached to B, preferably with at least one directly adjacent or conjugated carbonyl group,B is a group of formula ##STR1## and, if x is 2, 3 or 4, may also be one, two or three hydrogen atoms. The symbols Q, R.sub.1, R.sub.2, R.sub.3, R.sub.4, X, Y, Z, m und n, are as defined in claim 1. These carbamate group-containing soluble chromophores are distinguished by outstanding solid state fluorescence in the UV range as well as the by ease with which they can be converted to the corresponding pigments in the substrate in which they are incorporated.
    Type: Grant
    Filed: July 9, 1996
    Date of Patent: July 14, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Zhimin Hao, John S. Zambounis, Abul Iqbal
  • Patent number: 5772698
    Abstract: Compounds of the formula ##STR1## are described in which the variables are as defined in the claims and which are suitable as fiber-reactive dyes for dyeing a wide range of fiber materials.
    Type: Grant
    Filed: April 22, 1996
    Date of Patent: June 30, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Hans Reichert, Bernhard Muller
  • Patent number: 5696258
    Abstract: According to the invention, a process for the preparation of triphendioxazines symmetrically or asymmetrically amidated on both sides comprises reducing a triphendioxazine chromophore, which is optionally already amidated on one side, to give the leuco form and amidating and re-oxidizing the leuco form. Products amidated on both sides are obtained in this manner with a high yield and product quality. Novel triphendioxazine dyestuffs are furthermore prepared in this manner.
    Type: Grant
    Filed: November 8, 1996
    Date of Patent: December 9, 1997
    Assignee: DyStar Textilfarben GmbH
    Inventors: Christian Schumacher, Karl-Josef Herd
  • Patent number: 5656613
    Abstract: The invention concerns the treatment of hyperandrogenic conditions in humans by the formation of a novel mechanism-based irreversible inhibitor of human 5.alpha.-reductase enzymes from 3-oxo-4-azasteroids having a 1,2-double bond and the pyridine-nucleotide cofactor of the 5.alpha.-reductase enzyme, NADPH. Until the present invention, it was not known or predicted that 3-oxo-4-azasteroids having a 1,2-double bond would form a complex with NADPH by the mechanism of 5.alpha.-reductase in vivo. The invention further relates to the novel inhibitor-cofactor complex and pharmaceutical compositions containing the complex.
    Type: Grant
    Filed: January 4, 1995
    Date of Patent: August 12, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Herb G. Bull, Georgianna S. Harris
  • Patent number: 5650507
    Abstract: An asymmetric dioxazine compound of the following formula: ##STR1## wherein R is sulfo, halogeno, alkoxy, alkyl or carboxy; R.sub.1 and R.sub.2 are each hydrogen or alkyl; R.sub.3 is hydrogen, alkyl or acyl; X.sub.1 and X.sub.2 are each hydrogen, halogeno, alkyl, alkoxy or phenoxy; Y is aliphatic amino having a vinylsulfonyl or .beta.-substituted ethylsulfonyl fiber-reactive group; and Q is unsubstitued, substituted or cyclic amino; is useful for dyeing or printing fiber materials blue with excellence in build-up properties and various fastness properties.
    Type: Grant
    Filed: December 27, 1995
    Date of Patent: July 22, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kingo Akahori, Junya Hada, Takashi Omura, Shigeru Kawabata, Naoki Harada
  • Patent number: 5591834
    Abstract: Reactive dyestuffs of the formula ##STR1## in which Z is a cyano-free pyrimidine reactive group and the remaining groups have the meaning given in the description, are highly suitable for the dyeing and printing of hydroxyl- or amido-containing materials.
    Type: Grant
    Filed: December 22, 1994
    Date of Patent: January 7, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Konrad Bootz, Karl-Josef Herd
  • Patent number: 5585489
    Abstract: Triphendioxazine compounds corresponding to the formula (1) ##STR1## in which Z is a radical of the formula (2) ##STR2## in which Y.sup.1 and Y.sup.2 each vinyl .beta.-hydroxyethyl or an ethyl radical which contains a substituent which can be eliminated under alkaline conditions in the .beta.-position, and in which Y.sup.1 and Y.sup.2 are not simultaneously .beta.-hydroxyethyl, W.sup.1 and W.sup.2 are both allyene having 2 to 6 carbon atoms, A is a covalent bond of a group of the formula --B.sup.1 --N(R.sup.3)--, in which R.sup.3 has one of the meanings of R.sup.1 and B.sup.1 is an aliphatic or aromatic bridge member, and in which the group--N(R.sup.1) --B.sup.1 --N(R.sup.3)-- can also be in total a bivalent saturated heterocyclic radical, and Z.sup.0 is hydrogen or a group of the formula (4) ##STR3## in which A.sup.0 is a covalent bond or a radical or the formula --N(R.sup.4)--B.sup.2 -- having the meaning corresponding to the above formula --B.sup.1 (NR.sup.3)-- are described.
    Type: Grant
    Filed: May 4, 1995
    Date of Patent: December 17, 1996
    Assignee: Hoechst AG
    Inventors: Werner H. Russ, Christian Schumacher
  • Patent number: 5532362
    Abstract: The present invention is directed to a dioxazine dye which provides brilliant reddish blue dyeings possessing superior fastness properties and high tinctorial strength.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: July 2, 1996
    Assignee: Hoechst Celanese Corporation
    Inventors: Walter Helmling, David Brunetti, Uwe Reiher
  • Patent number: 5498712
    Abstract: A water-soluble triphenodioxazine dye having a chloro or bromo atom at one of the 6- and 13-positions and a group of Formula (1) at the remaining 6- or 13-position: ##STR1## wherein: R.sup.1 is H, OH or CH.sub.3 ; andR.sup.2 is C.sub.1-3 -alkyl, hydroxy-C.sub.1-3 -alkyl or --CH.sub.2 --(C.sub.1-4 -alkyl).The dyes are useful for the coloration of textile materials.
    Type: Grant
    Filed: May 13, 1993
    Date of Patent: March 12, 1996
    Assignee: Zeneca Limited
    Inventor: Gordon A. Thomson
  • Patent number: 5486607
    Abstract: A dioxazine compound represented by the following formula in the free acid form, ##STR1## wherein V is a direct linkage or ##STR2## in which R.sub.3 is hydrogen or alkyl, X is a direct linkage or an aliphatic, araliphatic or aromatic bridging group, Y is phenylene or naphthylene, Z is a so-called vinylsulfone type fiber reactive group, and R.sub.1 and R.sub.2 are each hydrogen or alkyl, which is useful for dyeing or printing fiber materials to give a dyed or printed product of a blue color superior in fastness properties with superior build-up property.
    Type: Grant
    Filed: January 27, 1995
    Date of Patent: January 23, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tetsuya Miyamoto, Miyao Takahashi, Takahiko Fujisaki, Naoki Harada, Yutaka Kayane, Takashi Omura
  • Patent number: 5478936
    Abstract: An asymmetric dioxazine compound represented by the following formula (I) in the free acid form: ##STR1## wherein A.sub.1 and A.sub.2 independently of one another are each sulfo, halo, alkyl or alkoxy, W is an unsubstituted or substituted aliphatic or aromatic bridging group, X.sub.1 and X.sub.2 independently of one another are each hydrogen, halo, alkyl, alkoxy or phenoxy, R.sub.1 and R.sub.2 independently of one another are each hydrogen or unsubstituted or substituted alkyl, R.sub.3 and R.sub.4 independently of one another are each hydrogen, halo, alkyl, alkoxy or unsubstituted or substituted amino, Z is a fiber-reactive group, m and n independently of one another are each 0 or 1, provided that m.noteq.n, and l is 1 or 2.
    Type: Grant
    Filed: March 21, 1994
    Date of Patent: December 26, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazufumi Yokogawa, Miyao Takahashi, Takahiko Fuzisaki, Yutaka Kayane, Shigeru Kawabata, Naoki Harada
  • Patent number: 5439486
    Abstract: Dye mixtures obtainable by condensing a compound of the formula ##STR1## and a compound of the formula ##STR2## with a compound of the formulaT--B--T (9)where the ring substituents are as defined herein, B is a bivalent organic linking group and T is halogen are suitable for use as direct dyes for dyeing and printing a wide range of materials and especially of cellulosic fibre materials, to give dyeings and prints of good allround fastness properties.
    Type: Grant
    Filed: September 3, 1993
    Date of Patent: August 8, 1995
    Assignee: Ciba-Geigy Corporation
    Inventor: Urs Lauk
  • Patent number: 5438137
    Abstract: An asymmetric dioxazine compound of the following formula in the free acid form, ##STR1## wherein R is hydrogen, halogen, sulfo or alkoxy, R.sub.1, R.sub.2 and R.sub.3 are each hydrogen or alkyl, X.sub.1 and X.sub.2 are each hydrogen, halogen, alkyl, alkoxy or phenoxy, Y is alkylene, phenylene or naphthylene, Z is --SO.sub.2 CH.dbd.CH.sub.2, --SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H or the like, V is hydrogen, alkyl, acyl or substituted triazinyl, and Q is halogen, alkoxy, amino or a group similar to that of ##STR2## provided that R is hydrogen, and Q is amino or a group similar to that of ##STR3## when V is substituted triazinyl, which is useful for dyeing or printing fiber materials to give dyed or printed products of a brilliant blue color superior in fastness properties, particularly those such as chlorine fastness with superior build-up property.
    Type: Grant
    Filed: September 30, 1993
    Date of Patent: August 1, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tetsuya Miyamoto, Miyao Takahashi, Takahiko Fujisaki, Shinei Ikeou, Takashi Omura, Naoki Harada
  • Patent number: 5378817
    Abstract: Reactive dyestuffs of the formula ##STR1## wherein Z=a heterocyclic reactive group and the remaining groups have the meaning given in the description, are outstandingly suitable for dyeing and printing materials containing hydroxyl groups or amide groups.
    Type: Grant
    Filed: January 15, 1993
    Date of Patent: January 3, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Konrad Bootz, Karl-Josef Herd
  • Patent number: 5310906
    Abstract: The novel triphendioxazine dyestuffs of the formula ##STR1## in which the substituents R, R', T.sub.1, T.sub.2, X, Y and n have the meanings given in the description are highly suitable for the dyeing and printing of cellulose-containing or amido-containing material.
    Type: Grant
    Filed: April 26, 1993
    Date of Patent: May 10, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventor: Horst Jager
  • Patent number: 5272267
    Abstract: An asymmetric dioxazine compound of the following formula in the free acid form, ##STR1## wherein R is hydrogen, halogen, sulfo or alkoxy, R.sub.1, R.sub.2 and R.sub.3 are each hydrogen or alkyl, X.sub.1 and X.sub.2 are each hydrogen, halogen, alkyl, alkoxy or phenoxy, Y is alkylene, phenylene or naphthylene, Z is --SO.sub.2 CH.dbd.CH.sub.2, --SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H or the like, V is hydrogen, alkyl, acyl or substituted triazinyl, and Q is halogen, alkoxy, amino or a group similar to that of ##STR2## provided that R is hydrogen, and Q is amino or a group similar to that of ##STR3## when V is substituted triazinyl, which is useful for dyeing or printing fiber materials to give dyed or printed products of a brilliant blue color superior in fastness properties, particularly those such as chlorine fastness with superior build-up property.
    Type: Grant
    Filed: July 17, 1992
    Date of Patent: December 21, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tetsuya Miyamoto, Naoki Harada
  • Patent number: 5268475
    Abstract: The compounds of formula (1) are suitable for use as direct dyes for dyeing and printing a wide range of materials, especially cellulosic fibers, to give dyeings and prints of good all-round fastness properties: ##STR1## wherein R and R.sub.1 are each independently of the other hydrogen or unsubstituted or substituted alkyl, cycloalkyl, aryl or aralkyl,X is a direct bond, --O--, --S-- or --N(R.sub.4)--, wherein R.sub.4 is hydrogen or unsubstituted or substituted alkyl, cycloalkyl, aryl or aralkyl, X.sub.1 is --O--, --S-- or --N(R.sub.4)--, wherein R.sub.4 is hydrogen or unsubstituted or substituted alkyl, cycloalkyl, aryl or aralkyl,Y and Y.sub.1 are each independently of the other C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, sulfo, carboxy, carbamoyl, N-mono- or N,N-di-C.sub.1 -C.sub.4 alkylcarbamoyl, N-phenyl- or N,N-diphenylcarbamoyl, sulfamoyl, N-mono- or N,N-di-C.sub.1 -C.sub.4 alkylsulfamoyl or N-phenyl- or N,N-diphenylsulfamoyl, Z and Z.sub.
    Type: Grant
    Filed: October 28, 1991
    Date of Patent: December 7, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Urs Lauk
  • Patent number: 5202436
    Abstract: The new triphendioxazine dyestuffs of the formula ##STR1## in which the substituents have the meaning given in the description are suitable for the dyeing and printing of cellulose-containing and amido-containing materials.
    Type: Grant
    Filed: March 7, 1991
    Date of Patent: April 13, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventor: Horst Jager
  • Patent number: 5171852
    Abstract: Triphenodioxazine reactive dyes, useful for dyeing cellulosic fibers, of the formula: ##STR1## wherein each of T.sup.1 and T.sup.2, independently, represents H, Cl, Br, F, SO.sub.3 H or an optionally substituted alkyl or aryl radical;R.sup.1 represents H or an optionally substituted hydrocarbon or heterocyclic radical;R.sup.2 represents an optionally substituted hydrocarbon radical;A represents C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, Cl, COOH or SO.sub.3 H, andn has a value of 0 or 1,the nature of the substituents being such that the dyes contain at least two SO.sub.3 H groups and at least two fibre-reactive groups.
    Type: Grant
    Filed: April 25, 1990
    Date of Patent: December 15, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Andrew H. M. Renfrew, Denis R. A. Ridyard, Brian Lamble
  • Patent number: 5128455
    Abstract: Water-soluble fiber-reactive dyes which contain one or more groups of the general formula (1) ##STR1## where R.sup..alpha. and R.sup..beta. are each hydrogen or lower alkyl,R is hydrogen or sulfoY is vinyl or ethyl which is substituted in the .beta.-position by a substituent which is eliminatable under alkaline conditions,W is hydroxy, N-morpholino, N-piperidinyl, N-pyrrolidinyl or a group of the general formula (2) ##STR2## where G is hydrogen or alkyl of 1 to 6 carbon atoms andQ is a group of the general formula (2a), (2b), (2c) or (2d) ##STR3##--(CH.sub.2).sub.t --R.sup.a (2b)--(CH.sub.2).sub.t --O--(CH.sub.2).sub.w --R.sup.a (2c)--(CH.sub.2).sub.t --R.sup.2 (2d)whereR.sup.a is a group of the general formula --SO.sub.2 --Y, where Y is as defined above, or sulfo,R.sup.b is hydrogen, alkoxy of 1 to 4 carbon atoms, sulfo, hydroxy, carboxy or chlorine,R.sup.
    Type: Grant
    Filed: December 21, 1989
    Date of Patent: July 7, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Springer, Patrick Scheidhauer, Karl-Michael Reichert, Guther Schwaiger, Kurt Hussong
  • Patent number: 5126450
    Abstract: Unsymmetrical triphendioxazine (TPD) reactive dyes of Formula (1) for the colouration of e.g. wool, silk, leather and cotton are claimed as well as intermediates for their manufacture. ##STR1## wherein W.sup.1 and W.sup.2 are different and each independently of the formula: ##STR2## R.sup.1 and R.sup.2 in each group defined by W.sup.1 or W.sup.2 independently represent H or an optionally substituted hydrocarbon radical or are joined together to form, with B and the two N atoms, a piperazine ring;each x independently has a value of 0 or 1;each B independently represents an optionally substituted divalent hydrocarbon radical;each Z independently represents a fibre-reactive group;T.sup.1 and T.sup.2 each independently represents H, Cl, Br, F, SO.sub.3 H or an optionally substituted alkyl or aryl radical;A.sup.1 and A.sup.2 each independently represents an alkyl, alkoxy, Cl, Br, COOH, SO.sub.
    Type: Grant
    Filed: November 1, 1990
    Date of Patent: June 30, 1992
    Assignee: Imperial Chemical Industries Plc
    Inventor: Peter Smith
  • Patent number: 5112970
    Abstract: Water-soluble triphendioxazine compounds of the formula (1) with quaternary ammonium groups ##STR1## in which the substituents are defined in claim 1. The compounds (1) have fiber-reactive dyestuff properties and dye, for example, cellulose fiber materials, wool and synthetic polyamide in deep, fast shades.
    Type: Grant
    Filed: August 23, 1989
    Date of Patent: May 12, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Holger M. Buch, Hartmut Springer
  • Patent number: 5068327
    Abstract: A dioxazine compound represented by the following formula (I) in the free acid form, ##STR1## wherein V is a direct linkage or ##STR2## in which R.sub.3 is hydrogen or unsubstituted or substituted alkyl, and X is a direct linkage or an aliphatic, araliphatic or aromatic bridging group, provided that X stands for the bridging group as defined hereinabove when V is ##STR3## Y is unsubstituted or substituted phenylene, or unsubstituted or substituted naphthylene, Z is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z.sub.1 in which Z.sub.1 is a group capable of being split by the action of an alkali, Q is sulfo, hydroxy, halo, alkoxy, unsubstituted or substituted phenoxy or unsubstituted or substituted amino, and R.sub.1 and R.sub.
    Type: Grant
    Filed: December 11, 1989
    Date of Patent: November 26, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tetsuya Miyamoto, Miyao Takahashi, Takahiko Fujisaki, Shinei Ikeou, Takashi Omura
  • Patent number: 5057609
    Abstract: Dyestuffs of the formula ##STR1## in which the substituents have the meanings given in the description are suitable for the dyeing and printing of hydroxy-containing and amido-containing materials. They produce blue dyeings having high color density and high light fastness and wet fastness properties.
    Type: Grant
    Filed: June 20, 1989
    Date of Patent: October 15, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Jager, Joachim Wolff
  • Patent number: 5019134
    Abstract: Triphenodioxazine reactive dyes containing at least one fiber-reactive group, the dye, in the free acid form, having the formula: ##STR1## wherein each of T.sup.1 and T.sup.2, independently, represents H, Cl, Br, F, SO.sub.3 H or an optionally substituted alkyl or aryl radical;each of A.sup.1 and A.sup.2 represents alkyl, alkoxy, Cl, Br, COOH, SO.sub.3 H or optionally substituted sulphamoyl;n has a value of 0, 1 or 2;m has a value of 1 or 2;R.sup.1 represents H or a group of the formula: ##STR2## wherein Z represents a fiber-reactive group;each of R.sup.2 and R.sup.3, independently, represents H or an optionally substituted hydrocarbon radical;B represents an optionally substituted divalent hydrocarbon radical; andD represents a group of the formula ##STR3## wherein R.sup.4 represents H, an optionally substituted hydrocarbon radical free from fiber-reactive residues or an acyl radical;R.sup.5 represents H or an optionally substituted hydrocarbon radical;R.sup.
    Type: Grant
    Filed: August 8, 1989
    Date of Patent: May 28, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Denis R. A. Ridyard, Peter Smith
  • Patent number: 4997937
    Abstract: Dyes suitable for dyeing and printing cellulose-containing fiber materials which produce blue dyeings and prints having good fastness properties. These dyes are of the formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, phenoxy, carboxyl carbamoyl or C.sub.1 -C.sub.4 alkanoylamino; R.sub.3 is hydrogen, sulfo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl, carbamoyl, N-C.sub.1 -C.sub.4 alkylcarbamoyl, N,N-di-C.sub.1 -C.sub.4 alkylcarbamoyl, C.sub.1 -C.sub.4 alkylsulfonyl, sulfamoyl, N-C.sub.1 -C.sub.4 alkylsulfamoyl or N,N-di-C.sub.1 -C.sub.4 alkylsulfamoyl; R.sub.4 is a radical of the formula ##STR2## R.sub.5 and R.sub.6 are independently of each other hydrogen or unsubstituted or hydroxyl-, sulfo-, sulfato-, carboxyl-, cyano-, halogen-, C.sub.1 -C.sub.4 alkoxycarbonyl-, C.sub.1 -C.sub.
    Type: Grant
    Filed: October 16, 1989
    Date of Patent: March 5, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Peter Aeschlimann
  • Patent number: 4990615
    Abstract: Triphendioxazine and triphendithiazine direct dyestuffs of the formula ##STR1## in which the substituents have the meanings given in the description produce on natural and synthetic OH-- and NH-- containing materials clear blue dyeings having good light and wet properties.
    Type: Grant
    Filed: September 12, 1989
    Date of Patent: February 5, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hermann Henk, Wolfgang Harms, Peter Wild
  • Patent number: 4923988
    Abstract: Triphendioxazines are prepared by cyclizing benzoquinone derivatives in oleum in the presence of an organic iodine compound.
    Type: Grant
    Filed: October 14, 1988
    Date of Patent: May 8, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Uwe Nahr, Manfred Pastsch
  • Patent number: 4886880
    Abstract: A process for the preparation of triphendioxazines of oxidising cyclisation of 2,5-diarylamino-1,4-benzoquinones with oleum and further optional oxidising agents and/or catalysts, which process comprises charging a reactor simultaneously with the 2,5 diarylamino-1,4-benzoquinone and oleum.
    Type: Grant
    Filed: June 28, 1988
    Date of Patent: December 12, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Holger Hahn, Rudolf Blattner
  • Patent number: 4885360
    Abstract: Reactive dyes of the formula ##STR1## in which D is the radical of a dye of the monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide series, R.sub.1 and R.sub.2, independently of each other, are each hydrogen or the radical of an unsubstituted or substituted hydrocarbon, A is an unsubstituted or substituted aliphatic or aromatic bridge member, n is 0 or 1, Y is a --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --X radical, X is an inorganic or organic radical detachable under alkaline conditions, Z is a radical of the formula ##STR2## and Hal is chlorine or bromine, and if n is 1 Z must not be either of the two radicals mentioned at the end for Z, are suitable for dyeing or printing cellulose fibre materials and produce lightfast and wetfast dyeings or prints.
    Type: Grant
    Filed: November 21, 1988
    Date of Patent: December 5, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Scheibli
  • Patent number: 4851527
    Abstract: Water-soluble triphendioxazine compounds of the formula ##STR1## having at least one sulfato or sulfo group, in which R is a hydrogen atom, a water-solubilizing group, an alkyl group having 1 to 6 carbon atoms which is substituted by an acidic group, or an optionally substituted sulfonamide group,B is an oxygen or sulfur atom or a group of the formula --NH--or --N(R')--, where R' equals optionally substituted alkyl, cycloalkyl which is optionally substituted by certain substituents, or optionally substituted phenyl, or naphthyl which is optionally substituted by sulfo and/or a --SO.sub.2 --Y' group,B.sup.1 has one of the meanings stated for B and is identical to B or different from B,W is a bivalent aliphatic, araliphatic or aromatic radical which may be interrupted by 1 or 2 hetero groups from the series comprising groups of the formulae --O--, --NH--and --N(R')--, where R' has the above meaning,W.sup.
    Type: Grant
    Filed: August 27, 1986
    Date of Patent: July 25, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Springer, Gunther Schwaiger, Walter Helmling
  • Patent number: 4845213
    Abstract: A novel, simple process for preparing triphendioxazines by oxidative cyclization of 2,5-diarylaminobenzoquinones in sulphuric acid which, if necessary, contains sulphur trioxide consists in using as an oxidizing agent chlorine, bromine or an inorganic bromine compound.
    Type: Grant
    Filed: June 6, 1988
    Date of Patent: July 4, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Josef-Walter Stawitz, Wolfgang Harms
  • Patent number: 4841049
    Abstract: Reactive dyes of the formula ##STR1## in which (R).sub.n stands for n substituents R which, independently of each other, can be C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, halogen, carboxyl, carbamoyl, N-C.sub.1-4 -alkylcarbamoyl, N,N-di-C.sub.1-4 -alkylcarbamoyl, C.sub.1-4 -alkylsulfonyl, sulfamoyl, N-C.sub.1-4 -alkylsulfamoyl or N,N-di-C.sub.1-4 -alkylsulfamoyl, n is 0 to 2, m is 1 to 2, one X is an H.sub.2 N group and the other X is a radical of the formula ##STR2## in which R.sub.1 and R.sub.2 are independently of each other hydrogen or substituted or unsubstituted C.sub.1-4 -alkyl, A is C.sub.2-4 -alkylene which can be substituted by halogen, hydroxyl, carboxyl, sulfo, phenyl, sulfophenyl or C.sub.1-4 -alkoxycarbonyl, or is cyclohexylene which can be substituted by C.sub.1-4 -alkyl, or in which the group --N(R.sub.1)--A--N(R.sub.
    Type: Grant
    Filed: September 3, 1987
    Date of Patent: June 20, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Karl Seitz
  • Patent number: 4816574
    Abstract: Water-soluble triphendioxazine compounds which have fiber-reactive properties as dyestuffs, which afford deep and fast dyeings on fiber materials, such as wool and, in particular, cellulose, and which correspond to the formula (1) ##STR1## in which: n is the number 0 or 1;Y is the vinyl group or an ethyl group containing, in .beta.-position, a substituent which can be eliminated by means of an alkali;Q.sup.1 and Q.sup.2 both represent a benzotriazole radical which can also be additionally substituted in the benzene nucleus by alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogen, carboxy or sulfo;B is --O--, --S--, --NH--or --N(R')--wherein R' is optionally substituted alkyl having 1 to 6 carbon atoms;W.sup.1 and W.sup.2 both represent a divalent, optionally substituted aliphatic, cycloaliphatic, aliphatic-cycloaliphatic, araliphatic or aromatic-carbocyclic radical, it being possible for the aliphatic radicals to be interrupted by hetero groups --O--, --S--, --SO.sub.
    Type: Grant
    Filed: July 23, 1987
    Date of Patent: March 28, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunther Schwaiger, Hartmut Springer, Walter Helmling