The Hetero Ring Consists Of Sulfur, Nitrogen And Carbon (e.g., Benzothiazole, Etc.) Patents (Class 534/788)
  • Publication number: 20120291207
    Abstract: Novel disperse azo dyes of formula (I), and processes for preparation thereof. These dyes possess superior washing fastness, sublimation fastness and light fastness.
    Type: Application
    Filed: December 23, 2010
    Publication date: November 22, 2012
    Applicant: COLOURTEX INDUSTRIES LIMITED
    Inventors: Pankaj Desai, Kiyoshi Himeno, Nikhil Desai
  • Publication number: 20110306742
    Abstract: This invention relates to coloured polymer particles preferably with surface functionality for charge retention, a process for their preparation, the use of these particles for the preparation of an electrophoretic device, colour electrophoretic displays comprising such particle, and new water-soluble dyes.
    Type: Application
    Filed: January 29, 2010
    Publication date: December 15, 2011
    Applicant: MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG
    Inventors: Louise Diane Farrand, Mark James, Matthias Koch, Ashley Nathan Smith, Jonathan Henry Wilson, Mark John Goulding, Daniel Walker
  • Patent number: 8070832
    Abstract: The invention provides for a dye of the formula (I) where D is the residue of a diazo component; R1 is hydrogen, (C1-C6)-alkyl, (C1-C4)-alkoxy, hydroxyl, halogen, —NHCHO, —NHCO(C1-C6)-alkyl or —NHSO2 (C1-C6)-alkyl; R2 is hydrogen, (C1-C6)-alkyl, (C1-C4)-alkoxy or halogen; R3 is hydrogen, (C1-C6)-alkyl, substituted (C1-C6)-alkyl, (C3-C4)-alkenyl or substituted (C3-C4)-alkenyl or R2 and R3 combine to form the radical —C*H(CH3)CH2C(CH3)2—, where the carbon atom marked * is attached to the phenyl nucleus; R4 is hydrogen or (C1-C6)-alkyl; R5 is hydrogen or (C1-C6)-alkyl; R6 is hydrogen or (C1-C6)-alkyl; X is phenyl, thiophenyl, sulfonylphenyl or phenoxy; n is 0, 1, or 2; and m is 0 or 1. The invention is also related to the process of using the dye and the process of preparing the dye.
    Type: Grant
    Filed: August 1, 2008
    Date of Patent: December 6, 2011
    Assignee: DyStar Colours Deutschland GmbH
    Inventor: Stefan Neubauer
  • Publication number: 20110247150
    Abstract: The invention provides for a dye of the formula (I) where D is the residue of a diazo component; R1 is hydrogen, (C1-C6)-alkyl, (C1-C4)-alkoxy, hydroxyl, halogen, —NHCHO, —NHCO(C1-C6)-alkyl or —NHSO2(C1-C6)-alkyl; R2 is hydrogen, (C1-C6)-alkyl, (C1-C4)-alkoxy or halogen; R3 is hydrogen, (C1-C6)-alkyl, substituted (C1-C6)-alkyl, (C3-C4)-alkenyl or substituted (C3-C4)-alkenyl or R2 and R3 combine to form the radical —C*H(CH3)CH2C(CH3)2—, where the carbon atom marked * is attached to the phenyl nucleus; R4 is hydrogen or (C1-C6)-alkyl; R5 is hydrogen or (C1-C6)-alkyl; R6 is hydrogen or (C1-C6)-alkyl; X is phenyl, thiophenyl, sulfonylphenyl or phenoxy; n is 0 , 1, or 2; and m is 0 or 1. The invention is also related to the process of using the dye and the process of preparing the dye.
    Type: Application
    Filed: August 1, 2008
    Publication date: October 13, 2011
    Applicant: DYSTAR COLOURS DEUTSCHLANDS GMBH
    Inventor: Stefan Neubauer
  • Publication number: 20110197377
    Abstract: The present invention relates to dyes of formula wherein R1 and R2 are each independently of the other hydrogen, vinyl, allyl or C1-C6alkyl which is unsubstituted or substituted by cyano, carboxy, hydroxy, C1-C6alkoxy or C6-C24aryl, R3 is hydrogen, C1-C6alkyl or C6-C24aryl, R4 is hydrogen, C1-C6alkyl or C6-C24aryl, 2-Cyano-C1-C6alkyl, 2-Alkoxy-C1-C6alkyl, 2-Oxo-C1-C6alkyl, n is 0, 1 or 2, and D denotes a radical of formula (2), (3), (4), (5), (6) or (7) wherein R5 is hydrogen, nitro, cyano or halogen, R6 and R7 are each independently of the other hydrogen, nitro, cyano or halogen, R8 and R9 are each independently of the other hydrogen, nitro, cyano or halogen, R10 and R11 are each independently of the other nitro, cyano, trifluoromethyl, carboxy, C1-C6alkyl, C1-C6alkoxy, C1-C6acylamino or halogen, R12 and R13 are each independently of the other hydrogen, nitro, cyano, trifluoromethyl, carboxy, C1-C6alkoxycarbonyl, C1-C6alkylsulfonyl, C1-C6alkylsulfonylamino, C1-C6acylamino or halogen, R14 represen
    Type: Application
    Filed: September 23, 2009
    Publication date: August 18, 2011
    Applicant: Huntsman International LLC
    Inventors: Ralf Petermann, Christian Suppiger, Urs Lauk
  • Patent number: 7875706
    Abstract: Disperse dyes of the general formula (I) where D is a diazo component derived from a substituted or unsubstituted aromatic amine, K is an aromatic radical of the formula and the substituents are each as defined in the first claim. Further described are the preparation and the use of the dyes according to the invention.
    Type: Grant
    Filed: December 2, 2004
    Date of Patent: January 25, 2011
    Assignee: Clariant Finance (BVI) Limited
    Inventor: Robert Egli
  • Patent number: 7871446
    Abstract: A dyestuff of the formula (I) wherein D is a diazo component; R1 is hydrogen, (C1-C4)-alkyl, hydroxy, —NHCOR6 or —NHSO2R6; R2 is hydrogen, halogen or (C1-C4)-alkoxy; R3 is hydrogen or methyl; R4 is hydrogen, (C1-C6)-alkyl, substituted (C1-C6)-alkyl, (C2-C6)-alkyl, which is interrupted by 1, 2 or 3 heteroatoms wherein said heteroatoms are —0—, —S— or —NR7, substituted (C2-C6)-alkyl, which is interrupted by 1, 2 or 3 heteroatoms wherein said heteroatoms are —0—, —S— or —NR7, (C2-C6)-alkenyl, substituted (C2-C6)-alkenyl, benzyl or phenethyl; R5 is hydrogen or methyl; R6 is (C1-C4)-alkyl, phenyl or substituted phenyl; R7 is (C1-C4)-alkyl, phenyl or substituted phenyl; m is 0, 1 or 2; and n is 0 or 1. The invention further relates to use of the dyestuff and the process of making the dyestuff.
    Type: Grant
    Filed: November 2, 2007
    Date of Patent: January 18, 2011
    Assignee: DyStar Colours Deutschland KG
    Inventors: Hartwig Jordan, Wolfgang Koster, Anthony Lawrence
  • Patent number: 7833291
    Abstract: The present invention provides dyes of the general formula (I) where D is the residue of a diazo component; R1 to R7 and L are each as defined in claim 1, processes for their preparation and their use.
    Type: Grant
    Filed: January 14, 2008
    Date of Patent: November 16, 2010
    Assignee: DyStar Textilfarben GmbH & Co. Deutschland KG
    Inventors: Hartwig Jordan, Stefan Neubauer, Anthony Lawrence, Nigel Hall
  • Publication number: 20100281629
    Abstract: The invention relates to a dye of the general formula (I) where D is the residue of a diazo component; R1 is hydrogen, (C1-C6-alkyl, (C1-C4)-alkoxy, hydroxyl, halogen, —NHCHO, —NHCO(C1-C6)-alkyl, —NHCOaryl, —NHSO2(C1-C6)-alkyl or —NHSO2aryl; R2 is hydrogen, (C1-C6)-alkyl, (C1-C4)-alkoxy, phenoxy or halogen; R3 is hydrogen, (C1-C6)-alkyl, substituted (C1-C6)-alkyl, (C3-C4)-alkenyl or substituted (C3-C4)-alkenyl; or R2 and R3 combine to form the radical —C*H(CH3)CH2C(CH3)2—, where the carbon atom marked * is attached to the phenyl nucleus; R4 is hydrogen, (C1-C6)-alkyl or phenyl; R5 is vinyl or a group of the formula —CHR6COR7, where R6 is hydrogen, (C1-C6)-alkyl or phenyl; R7 is (C1-C6)-alkyl, substituted (C1-C6)-alkyl, phenyl or substituted phenyl; and X is C1-C5)-alkylene. The invention for relates to a process to prepare the dye and their use.
    Type: Application
    Filed: September 15, 2008
    Publication date: November 11, 2010
    Applicant: DyStar Colours Deustschland GmbH
    Inventor: Stefan Neubauer
  • Patent number: 7824450
    Abstract: The present invention provides dyes of the general formula (I) where D, R1 to R7 and n are each as defined in claim 1, processes for their preparation and their use.
    Type: Grant
    Filed: October 16, 2007
    Date of Patent: November 2, 2010
    Assignee: DyStar Textilfarben GmbH & Co. Deutschland KG
    Inventors: Hartwig Jordan, Stefan Neubauer
  • Patent number: 7772377
    Abstract: Disclosed is a colorant composition of the formula wherein R is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, and wherein R can be joined to the phenyl moiety to form a ring, R? is an aromatic- or heteroaromatic-containing group, each Ra, independently of the others, is a halogen atom, an alkyl group, an alkoxy group, a nitrile group, a nitro group, an amide group, or a sulfonamide group, w is an integer of 0, 1, 2, 3, or 4, n is an integer representing the number of carbon atoms in each repeat alkylene oxide unit, and x is an integer representing the number of repeat alkylene oxide units, wherein said colorant has no more than one —OH, —SH, or primary or secondary amino group per molecule.
    Type: Grant
    Filed: January 25, 2008
    Date of Patent: August 10, 2010
    Assignee: Xerox Corporation
    Inventors: Jeffrey H Banning, Donald R Titterington, Clifford R King
  • Publication number: 20100092670
    Abstract: The present invention provides dyes of the general formula (I) where D, R1 to R7 and n are each as defined in claim 1, processes for their preparation and their use.
    Type: Application
    Filed: October 16, 2007
    Publication date: April 15, 2010
    Applicant: DyStar Textilfarben GmbH & Co. Deutschland KG
    Inventors: Hartwig Jordan, Stefan Neubauer
  • Publication number: 20100076182
    Abstract: The present invention provides dyes of the general formula (I) where D is the residue of a diazo component; R1 to R7 and L are each as defined in claim 1, processes for their preparation and their use.
    Type: Application
    Filed: January 14, 2008
    Publication date: March 25, 2010
    Inventors: Hartwig Jordan, Stefan Neubauer, Anthony Lawrence, Nigel Hall
  • Publication number: 20090056038
    Abstract: A hair dye composition containing an azo dye (1) or a salt thereof, (wherein R1 to R4 represents H, aliphatic hydrocarbon group, aryl group, halogen atom, acyl group, cyano group, acylamino group, or the like, wherein R1 and R2, and/or R3 and R4 may be coupled to form a 5- or 6-membered ring; X represents C or N, with the proviso that when X represents C, n stands for 1, and when X represents N, n stands for 0; A1, A2, A3 and A4 each represents N or represents C substituted by Y or having H, with the proviso that at least one of A1, A2, A3 and A4 is a nitrogen atom; and Y represents a substituent with the proviso that m stands for an integer from 0 to 3).
    Type: Application
    Filed: February 10, 2006
    Publication date: March 5, 2009
    Applicant: KAO CORPORATION
    Inventors: Masakazu Yamaguchi, Dominic Pratt, Yasuhiro Ishiwata
  • Patent number: 7358344
    Abstract: An azo dye represented by formula (I): A-N?N—B??formula (I) wherein, A represents a group having a substituent required for inducing an intramolecular nucleophilic substitution reaction with a nitrogen atom of a reduced azo group as a nucleophilic species when the azo group is reductively decomposed, the group forming a compound containing the nitrogen atom in a ring structure, and B represents an aromatic or hetero ring which is bound to the azo group through a carbon atom.
    Type: Grant
    Filed: November 4, 2004
    Date of Patent: April 15, 2008
    Assignee: Fujifilm Corporation
    Inventors: Yasuhiro Shimada, Yasuhiro Ishiwata, Makiko Yokoi
  • Patent number: 7358345
    Abstract: The present invention claims dyestuffs of formula (I), wherein D, R1 to R7 and n are defined as given in claim 1, a process for their preparation and their use
    Type: Grant
    Filed: October 15, 2004
    Date of Patent: April 15, 2008
    Assignee: Dystar Textilfarben GmbH & Co. Deutschland KG
    Inventor: Nigel Hall
  • Patent number: 6969759
    Abstract: Disclosed is a colorant composition of the formula wherein R is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, and wherein R can be joined to the phenyl moiety to form a ring, R? is an aromatic- or heteroaromatic-containing group, each Ra, independently of the others, is a halogen atom, an alkyl group, an alkoxy group, a nitrile group, a nitro group, an amide group, or a sulfonamide group, w is an integer of 0, 1, 2, 3, or 4, n is an integer representing the number of carbon atoms in each repeat alkylene oxide unit, and x is an integer representing the number of repeat alkylene oxide units, wherein said colorant has no more than one —OH, —SH, or primary or secondary amino group per molecule.
    Type: Grant
    Filed: May 25, 2004
    Date of Patent: November 29, 2005
    Assignee: Xerox Corporation
    Inventors: Jeffery H. Banning, Donald R. Titterington, Clifford R. King
  • Patent number: 6479647
    Abstract: Novel addition products of hydroxyl-protecting groups (such as isocyanates) with oxyalkylene-substituted intermediates, such as poly(oxyalkylenated) aniline compounds, for the eventual production of substituted, and substantially pure, colorants, particularly diazo and triphenylmethane derivatives, through the reaction of such intermediates with certain reactants are provided. These new colorants exhibit improved wax and/or oil solubility and high purity, particularly due to the inability of certain impurities to deleteriously react with the protected hydroxyl groups of either the intermediate or the colorant during and/or after formation thereof. A method for producing such novel colorants through utilization of these novel substantially pure colorant intermediates is also provided.
    Type: Grant
    Filed: September 6, 2001
    Date of Patent: November 12, 2002
    Assignee: Milliken & Company
    Inventor: Rajnish Batlaw
  • Publication number: 20020016260
    Abstract: The present invention provides a method for forming an azo colorant by reaction of a diazo compound and a coupler. The coupler has a leaving group at the coupling position thereof, such that a coupling reaction rate is faster than it would be if the coupler did not have the leaving group. The coupling reaction rate constant k is preferably 0.1 (s−1) or more.
    Type: Application
    Filed: April 18, 2001
    Publication date: February 7, 2002
    Inventors: Hisao Yamada, Mitsuyuki Tsurumi, Kazunori Nigorigawa
  • Patent number: 6191265
    Abstract: Azo dyes of the formula wherein the substituents are each as defined in the description, are useful for dyeing and printing synthetic textile materials.
    Type: Grant
    Filed: December 14, 1999
    Date of Patent: February 20, 2001
    Assignee: DyStar Textilfarben GmbH & Co. Deutschland KG
    Inventor: Rainer Hamprecht
  • Patent number: 5952328
    Abstract: The present invention is directed to novel benzothiazo and related heterocyclic group-containing inhibitors of cysteine or serine proteases. Methods for using the same are also described.
    Type: Grant
    Filed: November 12, 1997
    Date of Patent: September 14, 1999
    Assignee: Cephalon, Inc.
    Inventors: Ron Bihovsky, Gregory J. Wells, Ming Tao
  • Patent number: 5925150
    Abstract: A black colorant composition useful for coloring polyurethanes is provided having a red benzothiazole azo colorant which, when combined with a complementary blue and yellow colorant, exhibits low flairing.
    Type: Grant
    Filed: August 20, 1997
    Date of Patent: July 20, 1999
    Assignee: Milliken & Company
    Inventors: Mark Edward Ragsdale, David Jesse Moody, Eric B. Stephens
  • Patent number: 5877301
    Abstract: A benzothiazole azo dye for thermal transfer recording of the following formula (I): ##STR1## wherein R.sup.1 is a C.sub.3-8 branched chain alkyl group, R.sup.2 is a substituted or unsubstituted alkyl group, X is a hydrogen atom, a lower alkyl group, a formylamino group, a lower alkylcarbonylamino group, a lower alkoxycarbonylamino group or a benzoylamino group, Y is a chlorine atom or a bromine atom, and Z is a hydrogen atom, a chlorine atom or a bromine atom.
    Type: Grant
    Filed: November 17, 1997
    Date of Patent: March 2, 1999
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Yukichi Murata, Mio Ishida
  • Patent number: 5824117
    Abstract: The present invention relates to the dyestuff of the formula I ##STR1## modifications of this dyestuff which are stable during dyeing, processes for the preparation thereof and their use for dyeing and printing synthetic fiber materials.
    Type: Grant
    Filed: June 28, 1996
    Date of Patent: October 20, 1998
    Assignee: Dystar Japan Ltd.
    Inventors: Ulrich Buhler, Jurgen Kuhlwein, Hubert Kruse
  • Patent number: 5723587
    Abstract: Disperse dyes of formula ##STR1## wherein D is the radical of a diazo component of the benzene, naphthalene, diphenyl, azobenzene, thiophene, benzothiazole, benzisothiazole, thiazole, thiadiazole, indazole, benzotriazole, pyrazole, anthraquinone, naphtholimide, chromone or diphenylene oxid series;X is hydrogen, methyl, halogen or --NH--CO--R, wherein R is methyl, ethyl, propyl, isopropyl, ethoxy or amino;Y is hydrogen, halogen, methoxy or --O--(CH.sub.2).sub.n --OR', wherein R' is hydrogen, CH.sub.3 or CH.sub.2 CH.sub.2 CN, and n is an integer from 1 to 6;R.sub.3 is C.sub.1 -C.sub.6 alkyl, andR.sub.4 is hydrogen, C.sub.1 -C.sub.6 alkyl or alkyl.The dyes are particularly suitable for dyeing polyester textile material and are distinguished in particular by very good lightfastness.
    Type: Grant
    Filed: August 8, 1996
    Date of Patent: March 3, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Antoine Clement, Athanassios Tzikas
  • Patent number: 5719270
    Abstract: Azophenyl compounds of the formula: ##STR1## wherein R.sub.1 is an o-, p-directing substituent; R.sub.2 is a substituted or unsubstituted .beta.-hydroxyalkyl group; R.sub.3 is an aromatic carbocyclic or heterocyclic group which is mono- or poly-cyclic and is substituted or unsubstituted; and wherein the benzene ring A may contain one or more further substituents. The compounds are useful as dyestuffs (if they are themselves colored) or as intermediates in the preparation of dyestuffs.
    Type: Grant
    Filed: January 15, 1997
    Date of Patent: February 17, 1998
    Inventors: Steven Michael Partington, David Allan Clarke
  • Patent number: 5691458
    Abstract: There are described compounds which are represented by the formula ##STR1## The compounds are useful as dyes, and as intermediates and dye moieties in the preparation of compounds, which are particularly useful in imaging applications, such as, for example, diffusion transfer photographic systems.
    Type: Grant
    Filed: September 18, 1996
    Date of Patent: November 25, 1997
    Assignee: Polaroid Corporation
    Inventors: Michael J. Arnost, Peter Viski, David P. Waller, David C. Whritenour
  • Patent number: 5635607
    Abstract: The cationic or basic aminobenzothiazole dyes disclosed herein are particularly suitable for dyeing paper.Paper is dyed with these dyes in blue or violet shades of good fastness properties.
    Type: Grant
    Filed: April 21, 1995
    Date of Patent: June 3, 1997
    Assignee: Ciba-Geigy Corporation
    Inventor: Adolf Kaser
  • Patent number: 5608042
    Abstract: A monoazo dye of the following formula (I): ##STR1## wherein R is phenyl, phenoxy or benzyl, and D is a group of the formula (D1), (D2), (D3) or (D4): ##STR2## wherein each of X.sup.1, X.sup.2 and X.sup.3, which are independent of one another, is hydrogen or chlorine, X.sup.4 is hydrogen, chlorine, methyl or --NHCOR.sup.1, wherein R.sup.1 is C.sub.1-4 alkyl or phenyl; ##STR3## wherein X.sup.4 is as defined above, Y.sup.1 is hydrogen, chlorine or C.sub.1-4 alkoxy; ##STR4## wherein X.sup.5 is hydrogen, halogen, methyl or --NHZ, wherein Z is C.sub.1-4 alkylsurfonyl, C.sub.1-4 alkylcarbonyl, phenylsulfonyl, phenylcarbonyl, C.sub.1-2 alkoxy C.sub.1-2 alkylcarbonyl or aminocarbonyl, Y.sup.2 is hydrogen, methyl or C.sub.1-2 alkoxy, and Q.sup.1 is cyano or C.sub.1-4 alkylcarbonyl; ##STR5## wherein P is formyl, nitro or cyano, Q.sup.2 is cyano or nitro, T is halogen, methyl, phenyl or methylsulfonyl, X.sup.5 is as defined above, and Y.sup.3 is hydrogen or C.sub.1-2 alkoxy.
    Type: Grant
    Filed: January 31, 1996
    Date of Patent: March 4, 1997
    Assignee: Dystar Japan Ltd.
    Inventors: Kiyoshi Himeno, Toshio Hihara, Ryouichi Sekioka
  • Patent number: 5597905
    Abstract: Described is a process for preparing benzothiazolylazoanilines by diazotization of 2-aminobenzothiazoles in a mixture consisting essentially of phosphoric acid, sulfuric acid and water using customary diazotizing agents and subsequent addition of the reaction mixture to an aqueous acidic solution of the anilines.
    Type: Grant
    Filed: December 15, 1995
    Date of Patent: January 28, 1997
    Assignee: BASF Aktiengesellschaft
    Inventor: Rudolf Bermes
  • Patent number: 5567470
    Abstract: A blue dyestuff represented by the formula (2) ##STR1## wherein each of R.sub.1, R.sub.2 and R.sub.3 is independently a hydrogen atom, halogen atom, nitro group, hydroxy group, alkyl group which may have a substituent, alkoxy group, alkylsulfonylamino group or alkylcarbonylamino group, and each of R.sub.4 and R.sub.5 is independently an alkyl group which may have a substituent, and a heat-sensitive transfer sheet containing the above-mentioned dyestuff.
    Type: Grant
    Filed: August 18, 1995
    Date of Patent: October 22, 1996
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Hitoshi Koshida, Isamu Ghoda, Tsukasa Ohyama, Keisuke Takuma
  • Patent number: 5550218
    Abstract: Compounds of the formula ##STR1## wherein A is C.sub.1-6 alkylene, D is a diazo component radical of the triazolyl, pyrazolyl, cyano(C.sub.1-4 alkyl)-imidazolyl, 4-chlorothiazolyl, 4-chlorotheinyl-2, 3-phenyl-1,2,4-thiadiazolyl-5, isothiazolyl-5, benzoisothiazolyl-3 or 1,3,4-thiadiazolyl-5 series or the phenyl series wherein the phenyl group is free of sulfonyl groups and may be substituted, by a maximum of 3 substituents 5-nitrothiazolyl-2, ##STR2## R.sub.1a is phenyl or phenyl substituted by 1 to 4 substituents each of which is independently halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, trifluoromethyl, hydroxy, nitro, formyl, cyano, --SCN, (C.sub.1-4 alkyl)carbonyl, (C.sub.1-4 alkyl)carbonylamino, (C.sub.1-4 alkoxy)carbonyl, (C.sub.1-4 alkyl)carbonyloxy, carbamoyl, (C.sub.1-2 alkoxy)(C.sub.2-3 alkoxy)carbonyl or phenyl, andR.sub.2 -R.sub.4 and R.sub.10 -R.sub.
    Type: Grant
    Filed: October 6, 1994
    Date of Patent: August 27, 1996
    Assignee: Sandoz Ltd.
    Inventor: Ruedi Altermatt
  • Patent number: 5527888
    Abstract: A monoazo dye of the following formula (I): ##STR1## wherein R is phenyl, phenoxy or benzyl, and D is a group of the formula (D1), (D2), (D3) or (D4): ##STR2## wherein each of X.sup.1, X.sup.2 and X.sup.3, which are independent of one another, is hydrogen or chlorine, X.sup.4 is hydrogen, chlorine, methyl or --NHCOR.sup.1, wherein R.sup.1 is C.sub.1-4 alkyl or phenyl; ##STR3## wherein X.sup.4 is as defined above, Y.sup.1 is hydrogen, chlorine or C.sub.1-4 alkoxy; ##STR4## wherein X.sup.5 is hydrogen, halogen, methyl or --NHZ, wherein Z is C.sub.1-4 alkylsulfonyl, C.sub.1-4 alkylcarbonyl, phenylsulfonyl, phenylcarbonyl, C.sub.1-2 alkoxy C.sub.1-2 alkylcarbonyl or aminocarbonyl, Y.sup.2 is hydrogen, methyl or C.sub.1-2 alkoxy, and Q.sup.1 is cyano or C.sub.1-4 alkylcarbonyl; ##STR5## wherein P is formyl, nitro or cyano, Q.sup.2 is cyano or nitro, T is halogen, methyl, phenyl or methylsulfonyl, X.sup.5 is as defined above, and Y.sup.3 is hydrogen or C.sub.1-2 alkoxy.
    Type: Grant
    Filed: March 7, 1995
    Date of Patent: June 18, 1996
    Assignee: Dystar Japan Ltd.
    Inventors: Kiyoshi Himeno, Toshio Hihara, Ryouichi Sekioka
  • Patent number: 5342928
    Abstract: Azo dyes useful for dyeing or printing textile fibers or fabrics and containing novel aminobenzo heterocycles as diazo component have the formula ##STR1## where X is nitrogen or a radical of the formula CR.sup.6, where R.sup.6 is hydrogen, C.sub.1 -C.sub.4 -alkoxycarbonyl or C.sub.1 -C.sub.6 -alkanoyl,R.sup.1 and R.sup.2 are substituted or unsubstituted C.sub.1 -C.sub.10 -alkyl or substituted or unsubstituted C.sub.3 -C.sub.4 -alkenyl or additionally in the case of R.sup.1 hydrogen,R.sup.3 is hydrogen or C.sub.1 -C.sub.4 -alkoxy,R.sup.4 is C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy, substituted or unsubstituted C.sub.1 -C.sub.8 -alkanoylamino, C.sub.1 -C.sub.4 -alkylsulfonylamino, C.sub.3 -C.sub.4 -alkenoylamino or substituted or unsubstituted C.sub.1 -C.sub.4 -alkoxycarbonylamino, andR.sup.5 is hydrogen, nitro, halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio or cyano.
    Type: Grant
    Filed: April 30, 1993
    Date of Patent: August 30, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Roetsch, Helmut Hagen, Helmut Reichelt, Clemens Grund
  • 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: 5304222
    Abstract: A disperse dye mixture comprising from 20 to 80% by weight of a red disperse dye of the following formula (A) and from 20 to 80% by weight of a red disperse dye of the following formula (B): ##STR1## wherein R.sup.1 is --C.sub.2 H.sub.5 or --C.sub.2 H.sub.4 OCOCH.sub.3, R.sup.2 is --C.sub.2 H.sub.4 OCOCH.sub.3 or --C.sub.2 H.sub.4 CN, and R.sup.3 is hydrogen or --CH.sub.3.
    Type: Grant
    Filed: June 17, 1992
    Date of Patent: April 19, 1994
    Assignee: Hoechst Mitsubishi Kasei Co., Ltd.
    Inventors: Ryouichi Sekioka, Kouichi Seto
  • Patent number: 5278293
    Abstract: Azo dyestuffs of the formula ##STR1## having the substituent meanings given in the description, are outstandingly suitable for dyeing and printing materials containing hydroxyl groups and amide groups.
    Type: Grant
    Filed: October 31, 1990
    Date of Patent: January 11, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Josef Herd, Manfred Hoppe, Hermann Henk, Klaus Kunde, Frank-Michael Stuohr
  • Patent number: 5264032
    Abstract: Pigment preparation essentially comprisinga) at least one pigment from the class of azo, anthrapyrimidine, anthanthrone, quinacridone, perinone, diketopyrrolopyrrole, dioxazine, flavanthrone, indanthrone, isoindolinone, isoviolanthrone, perylene, phthalocyanine, pyranthrone or thioindigo pigments or a mixture of pigments belonging to various classes, andb) at least one dispersant of the formula (I) ##STR1## in which P, independently of the pigments mentioned in a), is a radical of an anthanthrone azo, quinacridone, perinone, diketopyrrolopyrrole, dioxazine, indanthrone, perylene, phthalocyanine or thioindigo pigment,R.sup.1 and R.sup.2, independently of one another, are hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.
    Type: Grant
    Filed: October 21, 1992
    Date of Patent: November 23, 1993
    Assignee: Hoechst AG
    Inventors: Erwin Dietz, Manfred Urban
  • Patent number: 5187265
    Abstract: The present invention relates to a chromogenic benzoisothiazolone polymer derivative for measuring the presence or appearance of thiols in an aqueous system.
    Type: Grant
    Filed: February 28, 1992
    Date of Patent: February 16, 1993
    Assignee: Miles Inc.
    Inventors: James P. Albarella, David L. Garling, Robert P. Hatch
  • Patent number: 5128457
    Abstract: Newly synthesized chromogenic thiol-indicating benzoisthiazolone derivatives having the structure: ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification, are useful in the detection of thiols, particularly in an aqueous system. This process comprises contacting the aqueous system with a chromogenic thiol-indicating benzoisothiazolone derivative as described herein. Chromophoric changes due to thiol-mediated reduction of the benzothiazolone derivative then occur. Such changes can be in a solution or on an indicator surface in contact or having been in contact with the aqueous system. The chromophoric changes, due to a bathochromic shift in characteristics light absorption upon reduction of the benzoisothiazolone derivative, are proportional to the amount or rate of appearance of thiols in the aqueous system.
    Type: Grant
    Filed: December 5, 1991
    Date of Patent: July 7, 1992
    Assignee: Miles Inc.
    Inventors: James P. Albarella, David L. Garling, Robert P. Hatch
  • Patent number: 5116958
    Abstract: Disperse dyes, which produce dyeings of excellent thermomigration fastness, consisting of a chromophore and a lactam or oxime radical which detaches on heating to leave an isocyanate or isothiocyanate group, which reacts with a suitable group in the environment. The disclosed dyes are described by the formula ##STR1## where F is the radical of a dye which is free of water-solubilizing groups,B is a bridge member or a direct bond,Z is O or S andV is the radical of a group H--V, where H--V is an oxime of the formula ##STR2## or a lactam of the formula ##STR3## in which R.sup.1 and R.sup.2 are each independently of the other substituted or unsubstituted alkyl or aryl, orR.sup.1 and R.sup.2 together with the carbon atom linking them form a cycloaliphatic ring,R is hydrogen or alkyl andn is an integer from 4 to 11.
    Type: Grant
    Filed: January 5, 1990
    Date of Patent: May 26, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Liechti, Martin Trottmann
  • Patent number: 5101021
    Abstract: Compounds of the formula ##STR1## and mixtures of such compounds, wherein each R.sub.1 is independently halo,R.sub.3 is hydrogen or methyl, with the proviso that when R.sub.5 is ethoxy, R.sub.3 must be methyl,R.sub.4 is hydrogen or methyl, andR.sub.5 is hydrogen: C.sub.1-2 alkyl; C.sub.1-2 alkyl monosubstituted by halo; phenoxymethyl; vinyl; C.sub.1-4 alkoxy; C.sub.2-5 alkoxy monosubstituted by C.sub.1-2 alkoxy or halo; allyloxy; phenoxy or benzyloxy,useful as disperse dyes for the dyeing of substrates such as polyester by, for example, the rapid dyeing method and substrates dyed therewith.
    Type: Grant
    Filed: May 25, 1990
    Date of Patent: March 31, 1992
    Assignee: Sandoz Ltd.
    Inventor: Ruedi Altermatt
  • Patent number: 5075429
    Abstract: A monoazo compound of the formula, ##STR1## wherein D is a heterocyclic or carbocyclic compound residue such as benzothiazolyl and phenyl, X is hydrogen, alkyl, alkoxy, halogeno, acylamino or the like, Y is hydrogen, halogeno, alkyl, alkoxy and the like, R.sub.1 is alkyl, R.sub.2 is C.sub.2 -C.sub.4 alkylene, B is a bridging group such as ##STR2## --O--, --S--, C.sub.1 -C.sub.6 alkylene and the like, and W.sub.1, W.sub.2, W.sub.3, Z.sub.1, Z.sub.2 and Z.sub.3 are independently hydrogen, alkyl, halogeno or the like, which is useful for dyeing hydrophobic fiber materials to give dyed or printed product of a deep color excellent in fastness properties, particularly those such as washing fastness, even after various finishing treatments of the product.
    Type: Grant
    Filed: October 10, 1989
    Date of Patent: December 24, 1991
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Jun Yamamoto, Yasuyoshi Ueda, Takashi Omura, Yosuke Yamamoto, Hideo Hattori, Junichi Sekihachi
  • Patent number: 5055567
    Abstract: The dyes according to the invention consist of a chromophore and a radical which, on heating, forms an isocyanate or isothiocyanate group. The latter reacts with a suitable group in the environment. Dyeings of excellent thermomigration fastness are obtained. The disclosed dyes are of the formulae ##STR1## where F is the radical of an azo, anthraquinone or tricyanovinyl dye which is free of water-solubilizing groups,B and B' are each independently of the other a direct bond or a bridge member, selected from the group consisting of a straight-chain or branched alkylene group having 2 to 8 C atoms or one of the following groups ##STR2## where R is hydrogen or C.sub.1 -C.sub.6 alkyl, n is an integer from 1 to 8 and m is an integer from 2 to 4,Z is O or S,V is a group which at a temperature between 180.degree. and 240.degree. C. is eliminated as a radical HV, andV' is a direct bond which is cleaved at a temperature between 180.degree. and 240.degree. C.
    Type: Grant
    Filed: April 10, 1989
    Date of Patent: October 8, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Liechti, Karl Emmenegger, Martin Trottmann
  • Patent number: 4997918
    Abstract: Novel cationic azo compounds of the formula ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.4 -alkylene, R.sub.2 is C.sub.1 -C.sub.4 -alkyl, R.sub.3 is C.sub.1 -C.sub.4 -alkyl, R.sub.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, acylamino or halogen, R.sub.5 is hydrogen, C.sub.1 -C.sub.4 - alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen, one or more or R.sub.5 independently of each other being present on the ring to which R.sub.5 is attached, and A is an anion. Also provided is the production, and the use of these novel compounds as dyes for dyeing and/or printing, especially polyacrylonitrile materials, neutral blue dyeings having in particular good fastness to light being obtained.
    Type: Grant
    Filed: May 6, 1987
    Date of Patent: March 5, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Zink
  • Patent number: 4994563
    Abstract: The azo dyes of the formula ##STR1## in which D is a diazo component, R.sub.1 and R.sub.2 independently of one another are each a C.sub.1 -C.sub.10 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or naphthyl radical each of which is substituted or unsubstituted, or R.sub.1 and R.sub.2, together with the nitrogen atom linking them, are a 5-membered, 6-membered or 7-membered ring each of which is unsubstituted or substituted by heteroatoms, R.sub.3 is hydrogen, halogen or a C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxy or phenoxy radical each of which is substituted or unsubstituted, X is --CO-- or --SO.sub.2 --, n is the number 1, 2, 3, 4, 5 or 6 and M is a cation, produce dyeings of good fastness properties on fibre materials containing nitrogen or containing hydroxyl groups. This application also relates to the preparation and use of said azo dyes and to intermediates utilized in the preparation of said azo dyes.
    Type: Grant
    Filed: June 27, 1989
    Date of Patent: February 19, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Harald Walter, Rudolf Hurter
  • Patent number: 4962040
    Abstract: 2-Hydrazono-4,6-dinitrobenzthiazolones of the formula ##STR1## in which X.sub.1 represents hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -hydroxyalkyl, C.sub.1 -C.sub.4 -sulphoalkyl or C.sub.1 -C.sub.4 -sulphatoalkyl, andX.sub.2 represents hydrogen or --SO.sub.2 X.sub.3, whereX.sub.3 may represent hydrogen, C.sub.1 -C.sub.8 -alkyl or optionally substituted aryl andX.sub.1 also represents a double bond between the cyclic nitrogen atom and the carbon atom 2 according to the formula II below: ##STR2## where X.sub.2 has the meaning specified under the above formula. These hydrazones may be employed in the preparation of azo dyestuffs and as color formers for detecting of biological substances, and in the determination of H.sub.2 O.sub.2.
    Type: Grant
    Filed: August 10, 1989
    Date of Patent: October 9, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Herbert Hugl, Aloysius Engel, Klaus Wehling
  • Patent number: 4912203
    Abstract: Thiophene based colorants useful for coloring thermoset resins such as polyurethanes being the formula; ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are selected from halogen, carboxylic acid, alkanoyl, aryloyl, carbocyclic forming polymethylene chains, alkyl, aryl, cyano, thioalkyl, dithioalkyl, thioaryl, dithioaryl, thiocyano, carboxyalkyl, carboxyaryl, amidoalkyl, amidodialkyl, amidoaryl, amidodiaryl, oxyalkyl, thioamidoalkyl, thioamidodialkyl, or hydrogen when an adjacent group is isobutyryl; R.sub.4, R.sub.5, and R.sub.7 are selected from hydrogen alkyl, oxyalkyl, sulfonamidoalkyl, sulfonamidoaryl, amidoalkyl, amidodialkyl, amidoaryl, amidodiaryl, halogen, thioalkyl and thioaryl; and R.sub.8 and R.sub.9 are selected from polyalkylene oxide, copolymers of polyalkylene oxides, and hydroxyalkylenes.
    Type: Grant
    Filed: May 17, 1988
    Date of Patent: March 27, 1990
    Assignee: Milliken Research Corporation
    Inventors: Edward W. Kluger, Patrick D. Moore
  • Patent number: 4889535
    Abstract: Compounds of the formula ##STR1## and mixtures thereof, wherien p1 R.sub.1 is hydrogen, chloro or bromo, p1 R.sub.2 is hydrogen, chloro, bromo or nitro, p1 R.sub.3 is hydrogen, chloro, bromo, nitro or --SCN, p1 R.sub.4 is hydrogen, chloro or bromo, p1 R.sub.5 is hydrogen or C.sub.1-4 alkyl, and p1 R.sub.5 is C.sub.8-14 alkyl,with the provisos that (i) at least one of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is other than hydrogen, (ii) when R.sub.3 is nitro or --SCN, R.sub.2 is other than nitro, and (iii) when two or more of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are halo, then R.sub.3 is one of those halos, are useful as disperse dyes for dyeing substrates such as synthetic and semi-synthetic, hydrophobic, high molecular weight organic materials.
    Type: Grant
    Filed: March 13, 1987
    Date of Patent: December 26, 1989
    Assignee: Sandoz Ltd.
    Inventor: Beat Henzi
  • Patent number: 4837308
    Abstract: A universally usable process for preparing azo dyestuffs by oxidative coupling consists in carrying out the oxidation in the presence of redox mediators with a standard potential of 0.2-1.5 volts and, if appropriate, an additional oxidizing agent with a standard potential of 0.25-2.5 volts, wherein the sum of the oxidation equivalents should be at least 4. The preferred redox mediator is iodine. The process is particularly suitable for the preparation of heteroaromatic azo dyestuffs using an aniline coupling component.
    Type: Grant
    Filed: January 12, 1988
    Date of Patent: June 6, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventor: Rainer Gerlach