Halogen Attached Directly To A Hetero Ring Or To An Alicyclic Ring By Nonionic Bonding Patents (Class 534/630)
  • Patent number: 10870777
    Abstract: An improved composition for protecting a vehicle, building, or airplane surface that will be painted or mechanically processed. For example, certain regions of a vehicle, building, or airplane may be masked in accordance with the present disclosure to protect those regions from paint overspray. The composition produces a film which adheres well to a surface to be protected, with few or no pinholes. Additionally, the composition can absorb any oil or grease present on the surface which can eliminate the need for towels and chemical solvents that may create toxic fumes, hazardous waste, and flammable hazards. Further, the material can be removed easily from the surface after use by peeling the film layer away from the surface.
    Type: Grant
    Filed: December 1, 2016
    Date of Patent: December 22, 2020
    Assignee: Kimberly-Clark Worldwide, Inc.
    Inventor: John Gavin MacDonald
  • Publication number: 20090036638
    Abstract: A contrast dye for preparing a lithographic printing plate includes at least one A, D, and B group wherein A represents a phosphorous containing group capable of reacting with the surface of a lithographic receiver; D represents a chromophore group absorbing light between 400 nm and 700 nm; and B represents an aliphatic group of at least 6 carbon atoms. A lithographic printing plate includes such a contrast dye.
    Type: Application
    Filed: December 5, 2006
    Publication date: February 5, 2009
    Applicant: AGFA GRAPHICS NV
    Inventors: Emiel Verdonck, Johan Loccufier
  • Publication number: 20080256726
    Abstract: Dye mixtures, comprising at least one dye of formula and at least one dye from the group of formulae wherein B1, B2 and B3 are each independently of the others an organic bridging member, Q1 is C1-C4alkyl, halogen or a radical —SO2-Z, Q2 and Q3 are each independently of the other C1-C4alkoxy, Q4 is C1-C4alkoxy, C1-C4alkyl, halogen or sulfo Q5 is C1-C4alkoxy, C1-C4alkyl, C1-C4alkanoylamino, ureido, halogen or sulfo, R1, R2, R3, R4, R5, R6, R7, R8 and R9 are each independently of the others hydrogen or unsubstituted or substituted C1-C4alkyl, k and q are each independently of the other the number 0 or 1, n and p are each independently of the other the number 0, 1 or 2, m is the number 0, 1, 2 or 3, t is the number 1, 2 or 3, X1, X2, X3, X4, X5 and X6 are each independently of the others halogen, and T1, T2 and T3 are each independently of the others a non-fibre-reactive substituent or a fibre-reactive radical of formula wherein (R10)0-2 denotes from 0 to 2 identical or different substi
    Type: Application
    Filed: November 6, 2006
    Publication date: October 23, 2008
    Inventors: Jean-Marie Sire, Athanassios Tzikas, Georg Roentgen
  • Publication number: 20040249136
    Abstract: Fibre-reactive trisazo compounds of the formula (I) 1
    Type: Application
    Filed: April 6, 2004
    Publication date: December 9, 2004
    Inventor: Markus Gisler
  • Publication number: 20040158049
    Abstract: The invention relates to basic mono- and bisazo compounds according to formula (I) 1
    Type: Application
    Filed: November 25, 2003
    Publication date: August 12, 2004
    Inventors: Friedrich Lehr, Reinhard Pedrazzi, Heidrun Schene
  • Publication number: 20040138434
    Abstract: Monoazo based yellow pigment compositions for image recording that are suitable as a well-balanced yellow coloring agent for image recording with favorable reproducibility of images and image retaining capacity, which is inexpensive and excellent in safety are provided.
    Type: Application
    Filed: November 25, 2003
    Publication date: July 15, 2004
    Applicant: SANYO COLOR WORKS, LTD.
    Inventors: Koichi Takahara, Kensuke Misono, Hidehiro Tamatome, Junichiro Sato, Kunji Kitamura
  • Publication number: 20040127693
    Abstract: According to the invention there are provided fiber-reactive dyestuffs which are compounds of the formula (I) 1
    Type: Application
    Filed: October 20, 2003
    Publication date: July 1, 2004
    Inventors: Roland Wald, Markus Gisler
  • Publication number: 20040059099
    Abstract: The present invention relates to reactive azo dyes of the formula (I) or an alkali metal salt thereof, wherein A is formula (i) or (ii) C is an optionally substituted aromatic or heteroaromatic residue; and R1, R2, B, D, Y, a, b, c, d and n are defined as given in claim 1, a process for preparing said dyes and a process for colouring fibre material, which comprises applying thereto said dyes.
    Type: Application
    Filed: November 15, 2002
    Publication date: March 25, 2004
    Inventor: Warren James Ebenezer
  • Publication number: 20040049019
    Abstract: Described are mixtures of fiber-reactive azo dyes whereby black dyeings, including prints, are obtained on hydroxyl- and/or carboxamido-containing fiber materials, such as cellulose fiber materials, wool and synthetic polyamide fibers. The dye mixtures comprise one or more disazo dyes conforming to the general formula (1), one or more monoazo dyes conforming to the general formula (3), one or more monoazo dyes of the general formula (4) and/or (4a), optionally one or more monoazo dyes (2) and optionally one or more monoazo dyes conforming to the general formula (3a), as described in claim 1.
    Type: Application
    Filed: October 7, 2003
    Publication date: March 11, 2004
    Inventor: Jorg Dannheim
  • Patent number: 6670457
    Abstract: Compounds of the formula in which the variables are as defined in the claims, which are suitable as fiber-reactive dyes for dyeing widely varying fiber materials, are described.
    Type: Grant
    Filed: August 16, 2002
    Date of Patent: December 30, 2003
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Rolf Deitz, Bernhard Müller, Athanassios Tzikas
  • Publication number: 20030158395
    Abstract: 1.
    Type: Application
    Filed: June 3, 2002
    Publication date: August 21, 2003
    Applicant: BASF Akiengesellschaft
    Inventors: Warren James Ebenezer, David Greenwood, Michael Gordon Hutchings, Michael Alan Rabjohns, Andrea Maria Zamponi
  • Publication number: 20030060608
    Abstract: Disclosed are compositions for printing recording materials, especially textile fibre materials, paper and papery substrates and plastic films and plastic transparencies by the inkjet printing process, including
    Type: Application
    Filed: September 20, 2002
    Publication date: March 27, 2003
    Inventors: Ludwig Hasemann, Reinhard Pedrazzi, Josef Geisenberger, Josef Ritter, Hans-Tobias Macholdt, Andreas Wuzik
  • Patent number: 6458167
    Abstract: The invention relates to dyeing compositions containing phenyl-azo-benzene compounds comprising at least one cationic group Z, Z being chosen from quaternized aliphatic chains, aliphatic chains comprising at least one quaternized saturated ring and aliphatic chains comprising at least one quaternized unsaturated ring, to the use of such compositions as direct dyes in dyeing applications for keratin substances, in particular human keratin fibers and especially the hair, and to the direct dyeing processes employing these compositions.
    Type: Grant
    Filed: January 18, 2000
    Date of Patent: October 1, 2002
    Assignee: L'Oreal S.A.
    Inventors: Alain Genet, Alan Lagrange
  • Patent number: 5969113
    Abstract: Compounds of the formula ##STR1## in which the variables are as defined in the claims, which are suitable as fibre-reactive dyes for dyeing widely varying fibre materials, are described.
    Type: Grant
    Filed: November 26, 1997
    Date of Patent: October 19, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Rolf Deitz, Bernhard Muller, Athanassios Tzikas
  • Patent number: 5569747
    Abstract: Azo class reactive dyestuffs have been found which have the general formula (1) ##STR1## and in which Z.sup.1 and Z.sup.2 represent a reactive group from the pyrimidine series, X represents SR.sup.1, OR.sup.2 or NR.sup.3 R.sup.4, and the remaining substituents have the meanings given in the description, which dyestuffs are particularly suitable for dyeing hydroxyl- and amido-containing fibres, in particular cotton.
    Type: Grant
    Filed: August 25, 1994
    Date of Patent: October 29, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Jager, Joachim Wolff
  • Patent number: 5466790
    Abstract: Azo dyes of the formula ##STR1## where L.sup.1 is hydrogen, C.sub.1 -C.sub.8 -alkyl or phenyl,L.sup.2 and L.sup.3 are each substituted or unsubstituted C.sub.1 -C.sub.8 -alkyl, or together a radical of the formula ##STR2## where n is 0, 1 or 2, Y.sup.1 and Y.sup.4 are hydrogen, hydroxymethyl, 1,2-dihydroxyethyl or a radical of the formula COO.sym.M.sup..crclbar. or SO.sub.3.sup..crclbar. M.sup..sym., Y.sup.2 and Y.sup.3 are halogen or hydroxymethyl, and M.sup..sym. is the equivalent of a cation,L.sup.4 is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.8 -alkyl, substituted or unsubstituted phenyl, halogen, C.sub.1 -C.sub.8 -alkoxy, substituted or unsubstituted phenoxy, C.sub.1 -C.sub.8 -alkylthio, C.sub.1 -C.sub.8 -alkylsulfonyl, substituted or unsubstituted phenylthio, substituted or unsubstituted phenylsulfonyl, C.sub.1 -C.sub.8 -alkoxycarbonyl, C.sub.3 -C.sub.6 -alkenyloxycarbonyl or phenoxycarbonyl,X is nitrogen or the radical C--L.sup.5, where L.sup.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: November 14, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Sabine Gruettner-Merten, Helmut Reichelt, Arno Lange, Helmut Degen
  • Patent number: 5373094
    Abstract: A water-soluble dye which contains a group of Formula (1): ##STR1## The dyes of Formula (1) can be used to dye materials including natural and artificial textile materials such as wool, silk, polymides and modified polyacrylonitrile fibers.
    Type: Grant
    Filed: June 24, 1993
    Date of Patent: December 13, 1994
    Assignee: Zeneca Limited
    Inventor: John A. Taylor
  • 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: 5233026
    Abstract: Reactive dyes of the formula ##STR1## in which D is a monoazo dye, R.sub.1 is hydrogen or a substituted or unsubstituted C.sub.1-4 alkyl radical, Z is an unsubstituted or substituted amino group, and X is a vinyl, .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-chloroethyl or .beta.-acetoxyethyl group, with the condition that Z is not a sulfo- or carboxyl-substituted phenylamino group when the triazine radical is bonded to the radical of 1,8-aminonaphthol-3,6- or -4,6-disulfonic acid, and the X--SO.sub.2 radical is bonded directly to an aromatic C atom, are suitable in particular for dyeing and printing cellulose-containing fiber materials by the cold pad-batch method and produce, in high dyeing yields, dyeings and prints having good fastness properties.
    Type: Grant
    Filed: August 2, 1991
    Date of Patent: August 3, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanassios Tzikas
  • Patent number: 5216136
    Abstract: Compounds of the formula ##STR1## and salts thereof, and their use as as reactive dyes for the dyeing and printing of hydroxy group- and nitrogen- containing organic substrates, e.g., leather, natural and synthetic polyamides and natural and regenerated cellulose.
    Type: Grant
    Filed: March 22, 1991
    Date of Patent: June 1, 1993
    Assignee: Sandoz Ltd.
    Inventor: Markus Gisler
  • Patent number: 5206376
    Abstract: A process for the preparation of 2-amino-5-formyl-4-halothiazoles by reaction, in a first stage, of thiourea with chloroacetic or bromoacetic acid in the presence of an N,N-disubstituted formamide, followed by treatment of the reaction mixture with a phosphoric trihalide and then with water in the presence of a base.
    Type: Grant
    Filed: April 2, 1991
    Date of Patent: April 27, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Wiesenfeldt, Karl-Heinz Etzbach
  • Patent number: 5095102
    Abstract: Reactive dyestuffs of the formula ##STR1## in which A=H, halogen, alkyl, alkoxy, acylamino or amino,B=H, alkyl or alkoxy,X=--CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --Y, whereY=a radical which can be removed under alkaline conditions andZ=a fibre-reactive radical.
    Type: Grant
    Filed: August 13, 1990
    Date of Patent: March 10, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Josef Herd, Manfred Hoppe, Hermann Henk, Rolf Brockmann, Frank-Michael Stohr
  • Patent number: 5003052
    Abstract: A reactive dye of the formula ##STR1## in which R is a radical of the formula ##STR2## or Z is .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-acetoxyethyl, .beta.-halogenoethyl or vinyl; V is hydrogen or a radicalZ--SO.sub.2 --CH.sub.2 --CH.sub.2 --in which z is as defined above; R.sub.1 is hydrogen or C.sub.1-6 -alkyl; alk, independently of each other, are polymethylene radicals having 2 to 6 C atoms or their branched isomers; K is a benzene, naphthalene or heterocyclic radical; m is 1 to 6, p is 1 to 6 and q is 1 to 6; and the benzene or naphthalene radical A is further unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.8 -acylamino, C.sub.1 -C.sub.4 -alkylamino, phenylamino, N,N-di-.beta.-hydroxyethylamino, N,N-di-.beta.-sulfatoethylamino, sulfobenzylamino, N,N-disulfobenzylamino, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkylsulfonyl, trifluoromethyl, nitro, cyano, halogen, carbamoyl, N-C.sub.1 -C.sub.
    Type: Grant
    Filed: May 11, 1988
    Date of Patent: March 26, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanassios Tzikas
  • Patent number: 4994564
    Abstract: Thien-3-ylazo dyes of the formula: ##STR1## where X is cyano, nitro, C.sub.1 -C.sub.6 -alkanoyl, substituted or unsubstituted benzoyl, substituted or unsubstituted phenyl or the radical COOR.sup.1 or CONR.sup.1 R.sup.2 where R.sup.1 and R.sup.2 are identical or different and each is independently of each other substituted or unsubstituted C.sub.1 -C.sub.8 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, C.sub.3 -C.sub.4 -alkenyl, substituted or unsubstituted phenyl or together with the nitrogen atom linking them a 5- or 6-membered saturated heterocyclic radical, and R.sup.2 may additionally be hydrogen, Y is hydrogen, cyano, C.sub.1 -C.sub.6 -alkanoyl, substituted or unsubstituted benzoyl, C.sub.1 -C.sub.4 -alkylsulfonyl, substituted or unsubstituted phenylsulfonyl, substituted or unsubstituted phenyl or the radical COOR.sup.1 or CONR.sup.1 R.sup.2 where R.sup.1 and R.sup.2 are each as defined above, Z is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.
    Type: Grant
    Filed: November 10, 1988
    Date of Patent: February 19, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Karl-Heinz Etzbach, Helmut Reichelt, Guenter Hansen, Ernst Schefczik, Helmut Hagen, Gunther Lamm
  • 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: 4960871
    Abstract: Monoazo colorants represented by the general formula (I): ##STR1## wherein: D represents ##STR2## (wherein X represents a hydrogen atom or a halogen atom, and Y represents a nitro group, a lower alkylsulfonyl group, a thiocyanic acid group or a halogen atom), or ##STR3## (wherein P represents a nitro group or a lower alkylsulfonyl group, and Q and T each represents a hydrogen atom, a halogen atom or a cyano group);R.sup.1 and R.sup.2 each represents an ethylene group or a propylene group;R.sup.3 and R.sup.4 each represents a hydrogen atom or an alkyl group which may be substituted by a lower alkoxy group or a lower alkoxyalkoxy group; andZ represents a halogen atom.This monoazo colorants include a reactive type pyridine-based monoazo dye suitable for use in dyeing of cellulose or cellulose/polyester mixed fibers in red to orange.
    Type: Grant
    Filed: February 17, 1989
    Date of Patent: October 2, 1990
    Assignee: Mitsubishi Chemical Industries Inc.
    Inventors: Toshio Hihara, Yukiharu Shimizu
  • Patent number: 4952681
    Abstract: Compounds of the formula I ##STR1## where X is fluorine, chlorine, bromine, SO.sub.2 E or unsubstituted or substituted hydroxyl or mercapto, E is alkyl, alkenyl, cycloalkyl, aralkyl, aryl, chlorine or unsubstituted or substituted hydroxyl or amino, Y is cyano, nitro, alkanoyl, aroyl, alkylsulfonyl, arylsulfonyl, carboxyl, a carboxylic ester group or unsubstituted or substituted carbamyl, T is hydrogen, C.sub.1 -C.sub.4 -alkyl, a radical which can be introduced by electrophilic substitution or a radical of the formula --CH.dbd.B, in which B is a radical of a methylene-active compound or of an amine, and K is a radical of a coupling component, are disclosed. They are useful for dyeing synthetic fibers or plastics.
    Type: Grant
    Filed: July 27, 1988
    Date of Patent: August 28, 1990
    Assignee: Sandoz AG
    Inventors: Guenter Hansen, Ernst Schefczik, Karl-Heinz Etzbach, Helmut Reichelt, Hermann Loeffler
  • Patent number: 4950305
    Abstract: Hydrophobic textile materials can be dyed or printed with one or more monoazo dyes of the formula ##STR1## in which R.sup.1 is fluoro, chloro or bromo;R.sup.2 is hydrogen or chloro; andR.sup.3 is allyl, alkyl having 1 to 4 carbon atoms, alkoxyalkyl having 2 to 4 carbon atoms in the alkyl portion and 1 to 4 carbon atoms in the alkoxy portion or cyanoalkyl having 2 to 4 carbon atoms.
    Type: Grant
    Filed: August 7, 1989
    Date of Patent: August 21, 1990
    Assignee: Cassella Aktiengesellschaft
    Inventors: Ulrich Buhler, Margareta Boos, Reinhard Kuhn
  • Patent number: 4935501
    Abstract: Reactive dyes of the formula ##STR1## in which D is the radical of a dye of the monoazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide series, R.sub.1 is hydrogen or an unsubstituted or substituted C.sub.1-4 -alkyl radical, and X is the vinyl, .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-chloroethyl or .beta.-acetoxyethyl group, are suitable in particular for dyeing and printing cellulose-containing fibre materials by the cold pad-batch method and produce, in high dyeing yields, dyeings and prints having good fastness properties.
    Type: Grant
    Filed: March 7, 1988
    Date of Patent: June 19, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanassios Tzikas
  • Patent number: 4929719
    Abstract: Reactive dyes which are particularly suitable for dyeing and printing cellulose containing fiber materials by the cold padbatch process and which produce, in high dye yield, dyeings and prints having good fastness properties containing the radical of an amine of the formula ##STR1## in which R is hydrogen, halogen, hydroxyl or sulfo, Z is a radical of the formula --CH.dbd.CH.sub.2 or --CH.sub.2 --CH.sub.2 --Y, Y is a detachable group, R' is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by --COOH, --CN, --OH or --SO.sub.3 H, and E is a radical of the formula ##STR2## in which R' and Z are as defined above, alk, alk' and alk" independently of one another are a C.sub.1 -C.sub.6 alkylene radical, U is hydrogen, halogen, hydroxyl, sulfato, C.sub.1 -C.sub.4 alkanoyloxy, cyano, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, carbamoyl or a radical --SO.sub.2 --Z in which Z is as defined above, V is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.
    Type: Grant
    Filed: August 10, 1989
    Date of Patent: May 29, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Hansrudolf Schwander, Athanassios Tzikas, Peter Aeschlimann
  • Patent number: 4918169
    Abstract: Reactive dyes suitable for dyeing and printing cellulosic fiber materials by the cold pad-batch process having the formula ##STR1## wherein Fa is a monoazo or polyazo, metal complex azo, anthraquinone, phthalocyanine, formazane, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, napthoquinone, pyrenequinone or perylene-tetracarbimide dye radical, X is halogen, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl, a sulfonic acid or phosphonic acid group or a quaternized ammonium group, r is 1 or 2, R is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy or phenyl, and A is a radical of the formula ##STR2## wherein R' is hydrogen, C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy or phenyl, C.sub.5 -C.sub.
    Type: Grant
    Filed: August 19, 1988
    Date of Patent: April 17, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Karl Hoegerle
  • Patent number: 4910299
    Abstract: Disperse dyes suitable for dyeing textile material composed of polyester dyes of the formula ##STR1## in which D is the radical of a substituted or unsubstituted, homocyclic or heterocyclic diazo component belonging to the series comprising thienyl, thiazolyl, isothiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, benzothiazolyl, benzoisothiazolyl, pyrazolyl, imidazolyl or phenyl,X is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, acylamino, halogen or a group of the formula -NH-CO-NHQ in which Q is hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,Y is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkoxy,R is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.2 -C.sub.12 -alkenyl or phenyl, or Y and R, together with the nitrogen atom and the two C atoms linking them, form a 5-membered ring or 6-membered ring,B is a l inear or branched C.sub.2 -C.sub.6 -alkylene radical,W is halogen, C.sub.
    Type: Grant
    Filed: December 2, 1987
    Date of Patent: March 20, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Angelo D. Casa, Peter Liechti, Max Dempfle
  • Patent number: 4904777
    Abstract: A thiophene-containing azo dye of the formula ##STR1## where R is substituted or unsubstituted alkyl, alkenyl, cycloalkyl or phenyl, X is hydrogen, halogen, hydroxyl, unsubstituted or substituted alkoxy, cycloalkoxy, phenoxy, mercapto, alkylthio, phenylthio, alkylsulfonyl, phenylsulfonyl or phenyl and Y is cyano, nitro, alkanoyl, substituted or unsubstituted benzoyl, alkylsulfonyl, phenylsulfonyl, Co-Z, where Z is unsubstituted or substituted phenoxy, amino, mono- or dialkyl-amino, pyrrolidino, piperidino, morpholino or N-alkyl-piperazino, and K is the radical of a coupling component is used as dyes for dyeing fiber material.
    Type: Grant
    Filed: October 19, 1987
    Date of Patent: February 27, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Karl-Heinz Etzbach, Guenter Hansen, Ernst Schefczik, Helmut Reichelt
  • Patent number: 4876334
    Abstract: Reactive dyes of the formula ##STR1## in which D is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye, B.sub.1 and B.sub.2 are independently of each other hydrogen or alkyl which has 1 to 4 carbon atoms and which can be substituted by halogen, hydroxyl, cyano, C.sub.1-4 alkoxy, C.sub.1-4 alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato, X is fluorine, chlorine, bromine, sulfo, alkylsulfonyl having 1 to 4 C atoms or phenylsulfonyl, B is a --CH.sub.2 --.sub.n or --O--CH.sub.2 --.sub.n radical, n is 1 to 6, R is a radical of the formula ##STR2## Z is .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-acyloxyethyl, .beta.
    Type: Grant
    Filed: February 1, 1988
    Date of Patent: October 24, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Paul Herzig
  • Patent number: 4843153
    Abstract: Thienothiophene dyes of the formula ##STR1## wherein Z is carboxylate, acyl, carboxyl, substituted or unsubstituted carbamoyl, cyano or nitro, X is hydrogen, fluorine, chlorine, bromine, Z or a group of the formula ##STR2## T.sup.1 and T.sup.2 are identical or different and each is independently of the other cyano, substituted or unsubstituted alkoxycarbonyl, alkenyloxycarbonyl, carbamoyl or alkylcarbamoyl and W is hydrogen, methyl or ethyl, Y is hydrogen, chlorine or bromine and K is the radical of a coupling component, are highly suitable for dyeing synthetic fibers, in particular polyesters wherein the dyeing obtained have good fastness properties.
    Type: Grant
    Filed: July 1, 1987
    Date of Patent: June 27, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Eilingsfeld, Karl-Heinz Etzbach, Guenter Hansen, Helmut Reichelt
  • Patent number: 4841036
    Abstract: A dis-azo dye for polyester fibers represented by the formula ##STR1## wherein Y is hydrogen or acetylamino and R.sup.1 and R.sup.2 are each C.sub.1 -C.sub.4 alkyl, cyanoethyl, acetoxyethyl or C.sub.1 -C.sub.4 alkoxyethyl.
    Type: Grant
    Filed: December 18, 1984
    Date of Patent: June 20, 1989
    Assignee: Mitsubishi Chemical Industries, Limited
    Inventors: Seiichi Imahori, Kiyoshi Himeno, Junji Yoshihara
  • Patent number: 4837269
    Abstract: Disazothiphene dyes of the formula ##STR1## where X is an electron withdrawing group, Z is an electron withdrawing group, D is the radical of a diazo component and K is the radical of a coupling component, are highly suitable for dyeing synthetic fibers, in particular polyesters.
    Type: Grant
    Filed: June 30, 1987
    Date of Patent: June 6, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Karl-Heinz Etzbach, Guenter Hansen, Ernst Schefczik, Helmut Reichelt
  • Patent number: 4826505
    Abstract: A monoazo pyridone compound of the following formula, ##STR1## wherein X is a member selected from hydrogen, halogeno, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, aralkoxycarbonyl, alkylsulfonyl, arylsulfonyl, carbamoyl, sulfamoyl or cyano, and R is alkyl, alkenyl, cycloalkyl, phenyl or anilino, with the provisos that X is a member selected from those defined above except for hydrogen, chloro, methyl and methoxy when R is ethyl, and X is a member selected from those defined above except for alkyl when R is iso-butyl, which is stable under dyeing conditions, and useful for dyeing hydrophobic fiber materials to give dyed products of a deep, fast and brilliant color of greenish yellow to orange.
    Type: Grant
    Filed: February 8, 1988
    Date of Patent: May 2, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masao Nishikuri, Kiyoyasu Hashimoto, Hideo Hattori
  • Patent number: 4766206
    Abstract: Disclosed are reactive dyes, and the use thereof, according to the formula(R--U).sub.n D--(X).sub.r,in which D is the radical of a monoazo, polyazo or metal complex azo dye; U is --CO-- or --SO.sub.2 --; R is a radical of the formula ##STR1## Z is sulfatoethyl, .beta.-thiosultafoethyl, .beta.-phosphatoethyl, .beta.-acetoxyethyl, .beta.-halogenoethyl or vinyl; alk is straight-chained or branched C.sub.1 -C.sub.6 -alkylene; Y is hydrogen, chlorine, bromine, fluorine, hydroxyl, sulfato, C.sub.1 -C.sub.4 -alkanoyloxy, cyano, carboxyl, alkoxycarbonyl having 1 to 5 C-atoms, carbamoyl or a radical --SO.sub.2 --Z in which Z is as defined above; V is hydrogen or C.sub.1 -C.sub.4 -alkyl unsubstituted or substituted by carboxyl, sulfo, C.sub.1 -C.sub.2 -alkoxy, halogen or hydroxyl or is a radical ##STR2## in which Z, alk and Y are as defined above; R.sub.1 is hydrogen or C.sub.1 -C.sub.6 -alkyl; alk' are independently of each other straight-chained or branched C.sub.2 -C.sub.
    Type: Grant
    Filed: September 24, 1986
    Date of Patent: August 23, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanassios Tzikas
  • Patent number: 4757136
    Abstract: Water-soluble azo compounds having fiber-reactive dye properties conforming to the formula ##STR1## in which D denotes a benzene or naphthalene ring;R.sup.1 denotes hydrogen, alkyl, alkoxy, sulfo or carboxy;R.sup.
    Type: Grant
    Filed: September 30, 1986
    Date of Patent: July 12, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Springer, Michael Kunze, Marcos Segal, Werner H. Russ
  • Patent number: 4693726
    Abstract: Process for dyeing cellulose fibers or cellulose blend fibers, which comprises dyeing the fibers mentioned with water-soluble reactive dyes which contain in the dye molecule at least once the structural element of the formula ##STR1## in which Y denotes a hydroxyl, hydroxymethyl, alkoxy C.sub.1 -C.sub.4, aldehyde, carboxamide, monoalkyl C.sub.1 -C.sub.4 -carboxamide, dialkyl C.sub.1 -C.sub.4 -carboxamide, monophenyl carboxamide, cyano, alkyl C.sub.1 -C.sub.4 -oxycarbonyl or sulfo group or a halogen atom, in an aqueous medium within the pH range 4-11.
    Type: Grant
    Filed: April 3, 1986
    Date of Patent: September 15, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Fritz Meininger, Peter Mischke, Gerd Konig, Hartmut Springer
  • Patent number: 4659806
    Abstract: Copper complexes of disazo dyestuffs of the formula ##STR1## wherein R, Z, K and A have the meaning given in the description, and their use for dyeing and printing materials containing hydroxyl groups or amide groups, such as textile fibres, filaments and fabrics of wool, silk or synthetic polyamide or polyurethane fibres, and for dyeing and printing natural or regenerated cellulose in shades which are fast to washing.
    Type: Grant
    Filed: June 11, 1980
    Date of Patent: April 21, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventor: Horst Jager
  • Patent number: 4602084
    Abstract: Monoazo dyes of the formula ##STR1## in which K is the radical of a coupling component of the benzene or naphthalene series or of the heterocyclic series, and R is a ##STR2## --CO--R.sub.2 or --SO.sub.2 --O--R.sub.2 group in which R.sub.1 is hydrogen or C.sub.1-4 -alkyl and R.sub.2 is a substituted or unsubstituted monosulfo-C.sub.1-12 -alkyl radical, a substituted or unsubstituted monosulfophenyl, disulfophenyl, monosulfonaphthyl or disulfonaphthyl radical, and X and Y, independently of each other, are hydrogen, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, halogen, C.sub.2-6 -alkanoylamino, C.sub.1-5 -alkylsulfonylamino or a substituted or unsubstituted phenyl or phenoxy radical, produce dyeings on polyamide material which have good light and wet fastness properties.
    Type: Grant
    Filed: July 8, 1983
    Date of Patent: July 22, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Hurter
  • Patent number: 4562248
    Abstract: Azo dyes having the general formula ##STR1## in which each of X, Y and Z are independently selected from H and a variety of substituents, preferably provided that at least one of X and Y is a substituent selected, for example, from --CN, halogen, alkyl, and alkylsulfonyl, and C is the residue of a phenol, naphthol, indole, imidazothiazole, pyrazolone, thiazole, isothiazole or pyrazole type disperse dye coupling component. These dyes which are unexpectedly non-phototropic produce yellow to orange shades on hydrophobic fibers and exhibit improvements in one or more properties such as dyeability, dye exhaustion rate, light fastness, nonblooming, pH stability, build, fastness to ozone and nitrogen oxide, crock and wash fastness, migration, transfer, and pH stability on polyester, polyamide and other fibers including cellulose ester.
    Type: Grant
    Filed: November 25, 1983
    Date of Patent: December 31, 1985
    Assignee: Eastman Kodak Company
    Inventors: Max A. Weaver, Jean C. Fleischer
  • Patent number: 4556707
    Abstract: The invention provides reactive dyestuffs of the formula ##STR1## wherein X is a fibre-reactive group of the triazine or pyrimidine series; R.sub.3 and R.sub.4 are each hydrogen; n is 0 or 1; and k is a pyridone or pyrimidone coupling component; the dyestuffs are particularly suitable for dyeing and printing natural and regenerated cellulose fibre materials and synthetic polyamide fibre materials.
    Type: Grant
    Filed: February 1, 1984
    Date of Patent: December 3, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hermann Henk
  • Patent number: 4544738
    Abstract: A dye of the formula ##STR1## wherein R.sup.1 is is fluorine, chlorine, bromine, methyl, ethyl, cyano, carboxyl, nitro, tribfluoromethyl, methylsulfonyl, phenylsulfonyl, acetyl, C.sub.1 -C.sub.4 alkoxy, phenoxy, chlorophenoxy or benzoyl; R.sup.2 is hydrogen, chlorine, bromine, methyl, ethyl, C.sub.1 -C.sub.4 alkoxy, benzthiazol-2-yl, 6-methylbenzthiazol-2-yl, acetylamino, carboxyl aminosulfonyl, or aminocarbonyl; R.sup.3 is hydrogen chlorine, bromine or methyl; R.sup.5 is hydrogen, methyl, methoxy or ethoxy; and X is fluorohydroxyphosphonyl or dihydroxyphosphonyl. The dye of the present invention is useful in the dyeing of cellulose-containing material, polyamides and leather. The high tinctorial strength of the dyes and the very good lightfastness and wetfastness properties of the dyeings are particularly noteworthy.
    Type: Grant
    Filed: September 24, 1980
    Date of Patent: October 1, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Baumann, Hermann Kaack
  • Patent number: 4542207
    Abstract: Monoazo dyes for dyeing polyester fibers represented by the formula: ##STR1## wherein D represents a substituted or unsubstituted thiazolyl, benzothiazolyl, thiadiazolyl or pyridyl group, X represents a hydrogen atom, a chlorine atom, a methyl group, a methoxy group or an acylamino group, Y represents a hydrogen atom, a chlorine atom, a methyl group, an alkoxy group or an alkoxyalkyl group, R.sup.1 represents a hydrogen atom, a substituted or unsubstituted alkyl, alkenyl or aryl group, and R.sup.2 represents a phenoxymethyl group, a phenoxyethyl group, a benzyl group or a tetrahydrofurfuryl group.Fibers which can be dyed with the azo dyes of the present invention include polyester fibers such as polyethylene terephthalate, a polycondensate between terephthalic acid and 1,4-bis (hydroxymethyl) cyclohexane or the like and blended or mixed fibers of the above-described polyester fibers with natural fibers such as cotton, silk or wool.
    Type: Grant
    Filed: April 7, 1983
    Date of Patent: September 17, 1985
    Assignee: Research Association Of Synthetic Dyestuffs
    Inventors: Toshio Niwa, Kiyoshi Himeno, Junji Yoshihara