Azo Patents (Class 534/573)
  • Patent number: 5169404
    Abstract: Use of water-insoluble monoazo dyestuffs of the formula I ##STR1## wherein R.sup.1 denotes alkyl having 1 to 6 C atoms, cyclopentyl, cyclohexyl, fluorine, chlorine, bromine, alkoxy having 1 to 4 C atoms or trifluoromethyl,R.sup.2 denotes alkyl having 1 to 7 C atoms andR.sup.3 and R.sup.4 independently of one another denote alkyl having 1 to 4 C atoms,for the sublimation transfer process.
    Type: Grant
    Filed: February 21, 1991
    Date of Patent: December 8, 1992
    Assignee: Cassella AG
    Inventors: Ulrich Buhler, Erika Kunz, Josef Ritter
  • Patent number: 5160348
    Abstract: Mixtures of dyestuffs of the formulae I to IV ##STR1## wherein the radicals have the meanings customary in dyestuff chemistry, are excellent substitute products for the expensive anthraquinone dyestuff Disperse Blue 56.
    Type: Grant
    Filed: December 17, 1991
    Date of Patent: November 3, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Hoppe, Dieter Wiegner, Klaus-Peter Sagner, Heinz D. Jordan, Horst Brandt
  • Patent number: 5160495
    Abstract: Monoazo dyestuffs useful for dyeing and printing hydrophobic fibers have the formula ##STR1## in which R.sup.1 denotes alkyl having 1 to 3 carbon atoms, R.sup.2 and R.sup.3 independently of one another denote alkyl having 2 to 5 carbon atoms and R.sup.4 denotes methyl or ethyl.
    Type: Grant
    Filed: October 29, 1990
    Date of Patent: November 3, 1992
    Assignee: Cassella Aktiengesellschaft
    Inventors: Ulrich Buhler, Reinhard Kuhn, Margareta Boos
  • Patent number: 5156971
    Abstract: A diagnostic test for environmental bacillus which comprises the steps of inoculating an agar growth medium comprising a nitrate source, luminol and 3-amino-L-tyrosine (3AT) with the sample, incubating the inoculated medium and determining the presence of the bacillus. The novel medium preferably comprises potassium nitrate, luminol, 3-amino-L-tyrosine and trypticase soy agar. Antibiotics and/or a specific bacteriophage may be added to the medium surface in localized areas to show specific bacterial lysis for identification. The novel medium and the methods of this invention are suitable for the identification of B. anthracis.
    Type: Grant
    Filed: January 15, 1992
    Date of Patent: October 20, 1992
    Inventors: Johnathan L. Kiel, John L. Alls, Richard A. Weber, Jill E. Parker
  • Patent number: 5151129
    Abstract: A process for the production of a pigment composition comprising precipitating a pigment coupling component from alkaline solution by adding to it an acid, in the presence of a pre-formed, water-soluble azo dyestuff; and subsequently coupling the precipitated coupling component, containing the azo dyestuff, with a pigment diazo or tetrazo component, ensuring that at no time is any substantial amount of uncoupled diazo or tetrazo component present, to form a pigment composition containing the water-soluble azo dyestuff.
    Type: Grant
    Filed: March 28, 1991
    Date of Patent: September 29, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Donald J. Morrison, David McGregor, James M. McCrae
  • Patent number: 5145953
    Abstract: A biscyclobutarene monomer is prepared having two cyclobutarene moieties bridged by a divalent radical having at least one azo linkage. The monomers can be polymerized to form polymers exhibiting outstanding thermooxidative stability at high temperatures for prolonged time periods.
    Type: Grant
    Filed: February 2, 1988
    Date of Patent: September 8, 1992
    Assignee: The Dow Chemical Company
    Inventors: Robert A. Kirchhoff, Alan K. Schrock
  • Patent number: 5144014
    Abstract: A monoazo lake which comprises a monoazo dye, a lake-forming metal and a water-insoluble metal salt of a rosin, and which is coated with the water-insoluble water salt of the rosin, the lake-forming metal being at least one metal selected from calcium, barium and strontium, the metal of the water-insoluble metal salt being at least one metal selected from zinc, aluminum, copper and manganese, and a process for the production of a monoazo lake coated with a water-insoluble metal salt of a rosin, which comprises carrying out the following steps (1) and (2) in the order of (1) to (2) or (2) to (1):(1) a step of forming a monoazo lake by forming a lake of a monoazo dye with a metal salt of at least one metal for formation of a lake of the monoazo dye selected from calcium, barium and strontium, and(2) a step of forming the water-insoluble metal salt of the rosin by insolubilizing the rosin with a metal salt of at least one metal for insolubilization of the rosin selected from zinc, aluminum, copper and manganese.
    Type: Grant
    Filed: August 8, 1990
    Date of Patent: September 1, 1992
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Hitoshi Sugamo, Nobuyuki Tomiya, Yusuke Watabe
  • Patent number: 5136029
    Abstract: A hydrolyzable silyl group-containing azo compound is represented by the following general formula (I): ##STR1## wherein A represents a group originating from an azo compound having one or more active hydrogen groups;R.sup.1 represents a monovalent organic group;R.sup.2 represents a divalent organic group;X represents a hydrolyzable group;Y represents --O--, --S--, ##STR2## m is an integer of 1 to 3; and n is an integer of 1 or 2;and process for producing the same is disclosed. The hydrolyzable silyl group-containing azo compound is used to prepare a hydrolyzable silyl group-containing vinyl polymer produced by polymerizing vinyl monomer as a radical polymerization initiator.
    Type: Grant
    Filed: October 17, 1989
    Date of Patent: August 4, 1992
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Hisao Furukawa, Katsuhiko Isayama, Yasushi Kato
  • Patent number: 5128454
    Abstract: The invention relates to a novel crystallographic modification (.beta.-modification) of the pigment of the formula I ##STR1## The .beta.-modification shows reflections in the Cu-K.sub..alpha. radiation X-ray diffraction spectrum at the following diffraction angles 2.theta. (accuracy .+-.0.2.degree.): at 21.95.degree. a maximum of high intensity, at 5.40.degree., 7.30.degree., 10.85.degree., 14.50.degree. and 27.60.degree. maxima of medium intensity and at 10.05.degree., 12.80.degree., 16.40.degree., 17.95.degree., 24.65.degree. and 25.80.degree. maxima of low intensity.The .beta.
    Type: Grant
    Filed: February 21, 1990
    Date of Patent: July 7, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Heinrich Frolich
  • Patent number: 5112958
    Abstract: The fibre-reactive formazan dyes of the formula ##STR1## in which R is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, cyano or nitro, X is fluorine or chlorine, Y is .beta.-chloroethyl or vinyl and n is the number 0, 1 or 2 produce dyeings which have good fastness properties on nitrogen-containing or hydroxyl-containing fibre materials.
    Type: Grant
    Filed: July 19, 1990
    Date of Patent: May 12, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Urs Lehmann, Josef Koller
  • Patent number: 5095101
    Abstract: The present invention provides compounds of the formula, ##STR1## in which both groups --NR.sub.1 R.sub.2 are identical; R.sub.1 is C.sub.2-4 alkyl, substituted by one or two hydroxy groups or by one --OR.sub.3 groups, where R.sub.3 is C.sub.1-4 alkyl or C.sub.2-4 hydroxyalkyl, andR.sub.2 is hydrogen, C.sub.2-4 hydroxyalkyl or --CH.sub.2 CH.sub.2 CN, provided that when R.sub.2 is --CH.sub.2 CH.sub.2 CN then R.sub.1 can only be --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OH,and mixtures of such compounds, which compounds are in free acid or salt form, and are useful for dyeing or printing hydroxy group- or nitrogen-containing organic substrates, especially leather and textiles containing or consisting of natural or synthetic polyamides or of natural or regenerated cellulose; the most preferred substrate is textile material containing or consisting of cotton.
    Type: Grant
    Filed: July 14, 1988
    Date of Patent: March 10, 1992
    Assignee: Sandoz Ltd.
    Inventor: Hans von Tobel
  • Patent number: 5076811
    Abstract: The fibre-reactive formazan dyes of the formula ##STR1## in which R is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, cyano or nitro, X is fluorine or chlorine, and n is the number 0, 1 or 2 produce dyeings which have good fastness properties on nitrogen-containing or hydroxyl-containing fibre materials.
    Type: Grant
    Filed: July 19, 1990
    Date of Patent: December 31, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Urs Lehmann, Josef Koller
  • Patent number: 5077396
    Abstract: Compounds of the formula ##STR1## wherein each A is independently linear or branched C.sub.2-6 alkylene or linear or branched C.sub.3-6 alkylene substituted by hydroxy,each D is independently the radical of a diazo component of the benzene, azobenzene or naphthalene series, E is a divalent radical attached to each --N.sup..sym. R.sub.3 R.sub.4 -- radical through an aliphatic carbon atom,each R.sub.1 is independently hydrogen, C.sub.1-4 alkyl, cyclohexyl, phenyl or phenyl(C.sub.1-2 alkyl),each R.sub.2 is independently hydrogen, cyano, --COOR.sub.5, --CONR.sub.6 R.sub.7 or ##STR2## wherein R.sub.5 is hydrogen, C.sub.1-4 alkyl or phenyl(C.sub.1-2 alkyl),each of R.sub.6 and R.sub.7 is independently hydrogen or C.sub.1-4 alkyl,each R.sub.8 is independently C.sub.1-4 alkyl, and r is 0, 1, 2 or 3,each R.sub.3 is independently C.sub.1-4 alkyl or C.sub.1-4 alkyl monosubstituted by halo, cyano, hydroxy or phenyl,each R.sub.4 is independently hydrogen, C.sub.1-4 alkyl or C.sub.
    Type: Grant
    Filed: May 14, 1990
    Date of Patent: December 31, 1991
    Assignee: Sandoz Ltd.
    Inventors: Helmut A. Moser, Roland Wald
  • Patent number: 5068319
    Abstract: The present invention relates to dyestuffs soluble in organic solvents having the structure: ##STR1## wherein R is CF.sub.3 or phenyl, R.sub.1 and R.sub.2 are the same or different substituent groups selected from the group consisting of hydrogen, hydroxy, halogen, C.sub.1 to C.sub.3 alkyl and C.sub.1 to C.sub.4 alkoxy, R.sub.3 is selected from the groups consisting of hydrogen, C.sub.1 to C.sub.3 alkyl, C.sub.1 to C.sub.3 alkoxy, COOH, and COOR.sub.5 wherein R.sub.5 is C.sub.1 to C.sub.4 alkyl, R.sub.6 is selected from the group consisting of hydrogen, sulfonyl, C.sub.1 to C.sub.3 alkyl, C.sub.1 to C.sub.3 alkoxy and halogen, and n is zero or a whole number ranging from 1 to 3. The dyestuffs of the invention are useful as light absorbers or antihalation agents in photosensitive compositions. They may also be used as dyeing agents for paper, fibers or films and as components in printing ink formulations.
    Type: Grant
    Filed: March 29, 1990
    Date of Patent: November 26, 1991
    Assignee: Hoechst Celanese Corporation
    Inventors: David M. Brown, Robert E. Potvin
  • Patent number: 5068318
    Abstract: The invention relates to compounds of formula I ##STR1## wherein R.sup.1 is C.sub.12 -C.sub.30 alkyl, R.sup.2 is hydrogen or C.sub.1 -C.sub.30 alkyl, R.sup.3 is C.sub.1 -C.sub.3 -alkyl or C.sub.1 -C.sub.3 alkoxy, R.sup.4 may have one of the meanings of R.sup.3 or is halogen, k and n are each independently of the other 0, 1 or 2, and R.sup.5 and R.sup.6 are each independently of the other C.sub.1 -C.sub.4 alkyl, any of which alkyl groups as defined herein may also be partly fluorinated or perfluorinated, with the proviso that R.sup.1 is alkyl of not less than 18 carbon atoms if R.sup.2 is hydrogen or alkyl of less than 12 carbon atoms.From these compounds it is possible to prepare molecular aggregates, especially LB layer systems, which have reversible thermochromic and solvatochromic properties. The invention also relates to intermediates of formula II ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and n are as defined above.
    Type: Grant
    Filed: May 15, 1990
    Date of Patent: November 26, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Gero Decher, Bernd Tieka
  • Patent number: 5066791
    Abstract: Pyridoneazo dyes of the formula ##STR1## where L is C.sub.2 - or C.sub.3 -alkylene, R is C.sub.1 -C.sub.3 -alkyl and n is 1, 2 or 3, are useful for dyeing polyester fabrics.
    Type: Grant
    Filed: February 14, 1990
    Date of Patent: November 19, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Guenter Hansen, Gunther Lamm, Hermann Loeffler
  • Patent number: 5055564
    Abstract: A monoazo lake pigment for use in inks and paints of the formula (I): ##STR1## whose X-ray diffraction pattern shows a high diffraction intensity at a diffraction angle (2.theta..+-.0.2.degree.; Cu-K.sub..alpha.) of 5.0.degree., moderate diffraction intensity at 25.0.degree. and relatively low diffraction intensities at 14.8.degree., 19.5.degree..
    Type: Grant
    Filed: September 15, 1988
    Date of Patent: October 8, 1991
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Nagatoshi Koyayashi, Hirohito Ando
  • Patent number: 5055566
    Abstract: A compound of the Formula (1): ##STR1## wherein R is H, SO.sub.3 A, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, NO.sub.2, OH or halogen;W, X, Y and Z are independently H or SO.sub.3 A; andA is NQ.sub.4 wherein at least one Q is a branched chain fatty C.sub.6-20 -aliph atic group.
    Type: Grant
    Filed: June 19, 1990
    Date of Patent: October 8, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Peter Gregory, Ronald W. Kenyon
  • Patent number: 5053495
    Abstract: A dye which, in the free acid form, has the formula ##STR1## wherein W is COOHX is selected from H, COOH, SO.sub.3 H, halo, hydroxy, nitro, cyano, C.sub.1-6 -alkyl, C.sub.1-6 -alkoxy and C.sub.1-6 -acylamino;Y is H, COOH or SO.sub.3 H;Z is H, COOH or SO.sub.3 H;R & R.sup.1 are each independently H or C.sub.1-6 -alkyl substituted by 0, 1 or 2 --COOR.sup.2 groups; andR.sup.2 is H or C.sub.1-6 -alkyl;provided that there are at least two COOH groups and that the number of COOH groups is equal to or greater than the number of SO.sub.3 H groups.The dye is adapted for the preparation of inks for use in ink jet printing in which it displays high water-fastness on paper.
    Type: Grant
    Filed: August 24, 1989
    Date of Patent: October 1, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: David Greenwood, Nigel Hughes, Ronald W. Kenyon, Suraj L. Hindagolla
  • Patent number: 5053496
    Abstract: The present invention generally relates to statistical monofunctional terminated reactive liquid rubbers including a statistical monofunctional carboxylic-terminated reactive liquid rubber, a statistical monofunctional amine-terminated reactive liquid rubber, and a statistical monofunctional epoxy-terminated reactive liquid rubber. These polymers are pourable, making them useful in a variety of applications particularly as toughening agents for epoxy resins to which they impart good physical properties.
    Type: Grant
    Filed: April 27, 1990
    Date of Patent: October 1, 1991
    Assignee: The BF Goodrich Company
    Inventors: Robert J. Bertsch, Alan R. Siebert
  • Patent number: 5051131
    Abstract: An azo pigment composition which forms a dispersion having high tinting strength and excellent clearness, transparency, fluidity and storage stability, and which is formed from a coupling reaction between a diazo component and a coupler component, and contains a compound represented by formula (I) ##STR1## wherein Q represents a diazo or coupler component moiety, A represents a divalent bonding group selected from a class consisting of --CONR'--, SO.sub.2 NR'--, --CH.sub.2 NH-- and --CH.sub.2 NHCOCH.sub.2 NH-- in which R' represents a hydrogen atom, alkyl group having 1 to 20 carbon atoms or aryl group,each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represents a hydrogen atom, alkyl group having 1 to 20 carbon atoms or alkenyl group having 2 to 20 carbon atoms, and R.sub.3 and R.sub.
    Type: Grant
    Filed: December 12, 1989
    Date of Patent: September 24, 1991
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Takahiro Yuasa, Kenzi Kitamura
  • Patent number: 5047517
    Abstract: The invention relates to a yellow monoazo pigment which is obtained by diazotization of 2-amino-4-chloro-5-methylbenzene-1-sulfonic acid, coupling of the diazonium compound with 1-(3'-sulfophenyl)-3-methyl-5-pyrazolone and subsequent laking of the coupling product to the calcium salt.The new pigment has excellent heat stability and bleeding fastness and good light stability. It is particularly suitable for the pigmenting of polymeric plastics in the mass.
    Type: Grant
    Filed: September 28, 1989
    Date of Patent: September 10, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Walter Deucker
  • Patent number: 5037961
    Abstract: Aryldiazosulphonates having polymerizable ethylenically unsaturated groups are excellent starting materials for water-soluble homopolymers and copolymers, which can be converted to water-soluble polymers by irradiation. Thus, the polymers can be utilized for the preparation of aqueous coating compositions.
    Type: Grant
    Filed: April 12, 1989
    Date of Patent: August 6, 1991
    Inventors: Oskar Nuyken, Thomas Knepper, Brigitte Voit, Stephen D. Pask
  • Patent number: 5032572
    Abstract: Polymers from ethylenically unsaturated monomers, cross-linked by a substituted divinylazobenzene are useful as pharmaceutical compositions for the delivery of medicaments. The polymers are degraded by the enzymes of the upper gastrointestinal tract or are transferred intact past the upper gastrointestinal tract, to deliver the medicament to the large intestine. In particular, the polymers contain divinylazobenzene compounds of the formulae ##STR1## wherein R.sub.1 and R.sub.2 are independently selected from the group consisting of H, (except that R.sub.1 and R.sub.2 are not both H), Cl, Br, I, NO.sub.2, NH.sub.2, RO, ArO, COOH or salts thereof, COOR, COOAr, CHO, COR, SO.sub.3 H or salts thereof, R or Ar and wherein R is alkyl of up to 18 carbon atoms and Ar is mono- or bicyclic aryl of up to 15 carbon atoms.
    Type: Grant
    Filed: August 12, 1988
    Date of Patent: July 16, 1991
    Assignees: Medical College of Ohio, Bowling Green State University
    Inventors: Murray Saffran, Douglas C. Neckers
  • Patent number: 5030247
    Abstract: Mixtures of azo pigments of the formulae ##STR1## wherein each R.sub.1 is independently C.sub.1-4 alkyl, andeach R.sub.2 is independently 1,4-phenylene; 1,4-phenylene substituted by 1 or 2 substituents independently selected from chloro, bromo, methyl, methoxy, trifluoromethyl (maximum of one) and nitro (maximum of one); 4,4'-diphenylene substituted by 1 or 2 substituents independently selected from chloro, bromo, methyl and methoxy, each substituent being in the 3- or 3'-position; 1,4-naphthylene or 1,5-naphthylene, the mixture containing from 8 to 20% mole of benzoic acid ester residues and from 92 to 80% mole of terephthalic acid ester residues, useful for pigmenting in the mass synthetic polymers, for example, polyethylene, polypropylene, polystyrene, polyvinyl chloride, synthetic leather and rubber latices.
    Type: Grant
    Filed: November 9, 1989
    Date of Patent: July 9, 1991
    Assignee: Sandoz Ltd.
    Inventor: Jurgen Goldmann
  • Patent number: 5026831
    Abstract: The invention relates to compounds of the formula (I) ##STR1## where D.sup.1 and D.sup.2 are each independently of each other unsubstituted or substituted aryl or hetaryl. The compounds are obtained by diazotizing one or more amines of the formula D-NH.sub.2 where D has the meaning D.sup.1 or D.sup.2 as per the formula (I) and coupling with 0.5 mole of 1,5-diazabicyclo[3.3.0]octane-2,4,6,8-tetrone per mole of total reacting diazonium salts. Depending on the presence and length of alkyl chains the compounds are suitable for use as pigments, disperse dyes or even fat dyes.
    Type: Grant
    Filed: November 10, 1988
    Date of Patent: June 25, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rudiger Jung, Reinhold Deubel
  • Patent number: 5006644
    Abstract: Complexes of the formula ##STR1## and salts thereof, wherein each of R.sub.1 -R.sub.4 is independently hydrogen, halo, nitro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, --NHCOR.sub.8, --COX or --SO.sub.2 Z,wherein R.sub.8 is C.sub.1-4 alkyl or phenyl,X is hydroxy, C.sub.1-4 alkoxy, phenoxy, substituted phenoxy, phenyl(C.sub.1-4 alkoxy), substituted phenyl(C.sub.1-4 alkoxy), C.sub.1-4 alkyl, phenyl, substituted phenyl, cyclohexyl, cyclohexyl substituted by 1 to 3 C.sub.1-4 alkyl groups, amino or substituted amino, andZ is --CH.sub.2 CH.sub.2 OSO.sub.3 H, --CH.dbd.CH.sub.2 or a significance of X with the exception of C.sub.1-4 alkyl,with the proviso that 1 to 3 of R.sub.1 -R.sub.4 are --SO.sub.2 Z or at least two of R.sub.1 -R.sub.4 are --COOH,each R.sub.5 is independently hydrogen, C.sub.1-4 alkyl or C.sub.1-4 alkyl monosubstituted by hydroxy, chloro or cyano,R.sub.6 is halo, hydroxy, C.sub.1-4 alkoxy, phenoxy, amino or substituted amino, andeach R.sub.
    Type: Grant
    Filed: January 7, 1987
    Date of Patent: April 9, 1991
    Assignee: Sandoz Ltd.
    Inventor: Friedrich Lehr
  • Patent number: 5003050
    Abstract: A water-soluble luminescent compound having repeating units of the formula: ##STR1## The product, which is a polymer having repeating units comprising diazo-linked luminol and hydroxyindole, is referred to as diazoluminomelanin (DALM), since one of the precursors to this product, 3-amino-L-tyrosine (3AT) is closely related to the biological substrates which are converted into melanin.Also provided is a method for preparing DALM which comprises reacting 3AT with an alkali metal nitrite, and reacting the resulting diazonium salt with luminol.DALM can be used for chemiluminescent immunoassays for biological and chemical agents; in radiofrequency and ionizing radiation dosimeters; and for RNA/DNA hybridization assays for viruses and genetic detection.
    Type: Grant
    Filed: March 7, 1990
    Date of Patent: March 26, 1991
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Johnathan L. Kiel, Gerald J. O'Brien
  • Patent number: 5001229
    Abstract: Basic dyestuffs of the formula ##STR1## or tautomeric forms thereof, whereinR.sub.1 and R.sub.2 stand for hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen,Q - E stands for C-S, C-O, C-NH or N.sup..sym. -N.sup..crclbar.,A stands for C.sub.1 -C.sub.4 -alkylene,W stands for the radical of an aliphatic mono-, di-, tri-, tetra-, penta-, hexa- or heptamine, which can be protonated or quaternized,n stands for 0 to 1.5 andp stands for 1.3 to 10,are suitable for dyeing materials which can be dyed with basic dyestuffs.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: March 19, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Franke, Peter Wild
  • Patent number: 5001226
    Abstract: Compounds of the formula ##STR1## 1:1 and 1:2 metal complexes thereof, salts of such compounds and metal complexes and mixture thereof, whereineach of B.sub.1 and B.sub.2 is independently hydroxy or amino,each D is independently ##STR2## wherein R is hydrogen, C.sub.1-4 alkyl, C.sub.5-6 cycloalkyl, phenyl, benzyl or phenylethyl,R.sub.1 is hydrogen, cyano, --COOR.sub.4, --CONR.sub.5 R.sub.6, --SO.sub.2 NR.sub.5 R.sub.6, ##STR3## wherein each R.sub.3 is independently hydrogen, C.sub.1-4 alkyl, --NR.sub.5 R.sub.6 or --CONR.sub.5 R.sub.6,R.sub.4 is C.sub.1-6 alkyl or phenyl(C.sub.1-3 alkyl),R.sub.7 is C.sub.1-4 alkyl,R.sub.8 is hydrogen or C.sub.1-4 alkyl, andR.sub.9 is --S--, --O-- or --NR.sub.5 --,R.sub.2 is hydrogen, hydroxy or C.sub.1-4 alkoxy,R.sub.2a is hydrogen, C.sub.1-4 alkyl or halo,M is hydrogen; C.sub.1-8 alkyl; (C.sub.1-4 alkoxy)C.sub.1-4 alkyl; C.sub.2-4 hydroxyalkyl; C.sub.5-6 cycloalkyl; C.sub.5-6 cycloalkyl substituted by 1 to 3 C.sub.1-4 alkyls; phenyl(C.sub.1-3 alkyl); phenyl (C.sub.
    Type: Grant
    Filed: December 19, 1989
    Date of Patent: March 19, 1991
    Assignee: Sandoz Ltd.
    Inventors: Helmut A. Moser, Roland Wald
  • Patent number: 4994561
    Abstract: A process for the preparation of an azo dye of formula ##STR1## wherein K is the .beta.-naphthol radical, X is hydrogen or nitro and M is an alkali metal ion or an ammonium ion, which process comprises coupling an aqueous solution containing 15 to 30 percent by weight of a diazo component of formula ##STR2## and 6 to 20 mol % of an ammonium salt, based on the molar amount of the diazo component, at a pH in the range from 10.5 to 11.5 and in an inert gas atmosphere, to a coupling component of formula ##STR3## in which formulae (2) and (3) above K and X are as defined for formula (1).The present invention makes it possible to obtain the claimed azo dyes in high yield.
    Type: Grant
    Filed: June 8, 1990
    Date of Patent: February 19, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans P. Joswig, Werner Huber
  • Patent number: 4994111
    Abstract: The dye of the formula: ##STR1## which is suitable for use in aqueous inks, especially for ink jet printing.
    Type: Grant
    Filed: November 30, 1989
    Date of Patent: February 19, 1991
    Assignee: Canon Kabushiki Kaisha
    Inventors: Arthur Quayle, Cecil V. Stead
  • Patent number: 4994562
    Abstract: The fibre-reactive formazan dyes of the formula ##STR1## where B is an aliphatic or sulfo-free aromatic bridge member, R is .alpha.,.beta.-dihalopropionyl, .alpha.-haloacryloyl or haloacetyl, T.sub.1 is halogen, X is halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, cyano or nitro, Y is --CO-- or --SO.sub.2 --, Z is nitrogen or --C--T.sub.2, T.sub.2 is halogen, hydrogen, C.sub.1 -C.sub.4 alkylthio, cyano, formyl or C.sub.1 -C.sub.4 alkylsulfonyl, m is 1, 2 or 3, n is 0, 1 or 2, qu is 0 or 1 and r and s are each eitehr 0 or 1 but never the same as each other, produce dyeings having good fastness properties on nitrogen-containing or hydroxyl-containing fibre materials.
    Type: Grant
    Filed: June 29, 1989
    Date of Patent: February 19, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Urs Lehmann
  • 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: 4990598
    Abstract: The invention relates to chromium complexes of the formula ##STR1## in which A is the radical of a dicyclically metallizable azo or azomethine dye, B is the radical of a monoanionic bidentate complexible organic compound which is bonded to the chromium atom via oxygen atoms, L is a colorless monofunctional ligand, X is halogen-substituted C.sub.1-4 -alkanoyl, C.sub.1-4 -alkenoyl, halogen-substituted C.sub.1-4 -alkenoyl, monohalogenopyrimidinyl, dihalogenopyrimidinyl or trihalogenopyrimidinyl which is bonded to A and/or B via ##STR2## and R.sub.5 is hydrogen or C.sub.1-4 -alkyl, Ka is a cation, m is 1, 2 or 3, n is 1 or 2 and the SO.sub.3.sup..crclbar. Ka group is bonded to A and/or B. These chromium complexes are suitable for dyeing nitrogen-containing or hydroxy-containing materials and they produce level dyeings having good all-round fastness properties.
    Type: Grant
    Filed: November 7, 1984
    Date of Patent: February 5, 1991
    Inventors: Hans U. Schutz, Ulrich Schlesinger, Gerhard Back
  • Patent number: 4985546
    Abstract: A substituted colorant which may be copolymerized with a condensation polymer to provide a covalently bound, nonextractable coloring, having the formula ##STR1## wherein R and R.sub.1 are independently selected from hydrogen or lower alkyl; R.sub.4 is selected from hydrogen or lower alkyl; x is 0 or 1; N and M are each integers of from 1 to about 100 and the sum of N and M is from 3 to about 100. The hydroxyl groups are protected by formation of a ring structure during alkoxylation and amination of the substituent.
    Type: Grant
    Filed: June 19, 1989
    Date of Patent: January 15, 1991
    Assignee: Milliken Research Corporation
    Inventors: John W. Miley, John W. Rekers
  • Patent number: 4985045
    Abstract: A monoazo dyestuff composition comprising at least two different individual compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2, independently of each other, are linear or branched alkyl having 1 to 4 carbon atoms and R is linear or branched alkyl having 1 to 5 carbon atoms, and where said individual compounds differ from each other in at least the R moiety, has improved dyeing properties compared with the individual dyestuffs when used to dye or print hydrophobic fiber materials.
    Type: Grant
    Filed: October 30, 1989
    Date of Patent: January 15, 1991
    Assignee: Cassella Aktiengesellschaft
    Inventors: Ulrich Buhler, Klaus Hofmann
  • Patent number: 4985043
    Abstract: Mixtures of monoazo dyes suitable for dyeing and printing hydrophobic fiber materials and mixtures thereof with natural fibers contain one or more dyes of the formula I ##STR1## and one or more dyes of the formula II ##STR2## in which Hal denotes bromo or chloro; R.sup.1 and R.sup.2, independently of one another, denote methyl or ethyl; R.sup.3, R.sup.4, R.sup.5 and R.sup.6, independently of one another, denote linear alkyl having 1 to 4 carbon atoms or alkenyl having 3 or 4 carbon atoms; and R denotes methyl, acetylamino, propionylamino, i-butyrylamino, or n-butyrylamino.
    Type: Grant
    Filed: March 15, 1989
    Date of Patent: January 15, 1991
    Assignee: Cassella Aktiengesellschaft
    Inventors: Ulrich Buhler, Manfred Hahnke, Reinhard Kuhn, Margarete Boos
  • Patent number: 4981612
    Abstract: An optical element, such as a wave guide, having non-linear optical properties, suitable for use in optical devices in which it is desirable to alter the characteristics of the light, comprising a transparent or reflecting substrate having at least a partial superficial coating comprising alternating monolayers of a first non-linear optical (NLO) compound of the formula: ##STR1## wherein R is an non-hydrophilic aliphatic or cycloaliphatic group containing from 8 to 40 carbon atoms;m is 1 or 2;R.sup.1 is NO.sub.2, CN or COOR.sup.2 ;R.sup.2 is H or C.sub.1-4 -alkyl;n is from 1 to 4; andR.sup.3 is H, a metal or a group containing a tetravalent N atom anda second NLO compound of the formula: ##STR2## wherein T is H, a metal or a group containing a tetravalent N atom;X is S, O, ##STR3## T.sup.1 is NO.sub.2, CN or COOY; Y is selected from H, C.sub.1-4 -alkyl, a metal or a group containing a tetravalent N atom;T.sup.2 and T.sup.
    Type: Grant
    Filed: May 5, 1988
    Date of Patent: January 1, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Simon Allen, Paul F. Gordon, Joseph Zyss
  • Patent number: 4981489
    Abstract: Disazo compounds based on 4,4'-diaminodiphenyl compounds contain not less than 50% by weight of a disazo compound of the general formulaA--N.dbd.N--Z--N.dbd.N--B (I)where Z is a radical of an unsubstituted or symmetrically substituted diphenylene, A is a radical of a coupling component of a 1-phenylpyrazolone or of an acetoacetarylide, where the phenyl and the aryl radical is subtsituted by sulfo or carboxyl groups, and B is a radical of a coupling component based on 1-phenylpyrazolone or acetoacetarylide, which are free of sulfo and/or carboxyl groups.The disazo compounds can be obtained by coupling the tetrazotized diamine H.sub.2 N--Z--NH.sub.2 to the coupling component AH containing an acidic group in a medium containing a mineral acid, and then coupling the product to BH in a buffered medium (pH about 4).The novel disazo compounds are suitable as additives to pigments, in particular azo and disazo pigments, for improving the transparency and heat stability of the pigment particles, and the flow behavior.
    Type: Grant
    Filed: October 23, 1989
    Date of Patent: January 1, 1991
    Assignee: BASF Lacke & Farben Aktiengesellschaft
    Inventors: Wolfgang Ruff, Egon Liedek, Gerhard Berger, Hans W. Sonneborn
  • Patent number: 4980458
    Abstract: Mixed crystals of at least two different compounds of formula I ##STR1## wherein R is --CH.sub.3, phenyl, --COOCH.sub.3, --COOCH.sub.3, --COOC.sub.2 H.sub.5, --NHCO--C.sub.1 -C.sub.4 alkyl or --CONH--C.sub.1 -C.sub.4 alkyl, M.sup.+ and M.sub.1.sup.+ are each independently of the other an alkali metal cation, an alkaline earth metal cation or a heavy metal cation or NH.sub.4.sup.+ ; wherein X, Y, X' and Y' are each independently hydrogen, halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5, --NO.sub.2 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, wherein at least two of the cations M.sup.+ and M.sub.1.sup.+ in the compounds forming the mixed crystals of formula I are different and the X-ray diffraction patterns of the mixed crystals differ from the X-ray diffraction patterns of the individual components and of their sum.
    Type: Grant
    Filed: May 8, 1989
    Date of Patent: December 25, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Stefan Hari, Arnold Grubenmann, Andreas Burkhard
  • Patent number: 4978747
    Abstract: Colorants are obtained by reacting a dyestuff which is free from ionic groups and has.gtoreq.2 NH.sub.2 groups which are preferably arranged in such a manner that they do not participate in the resonance of the chromophore with such an amount of a (cyclo)aliphatic diisocyante so as to form an adduct that still contains at least two free NCO groups, and subsequently reacting this adduct with a (cyclo)aliphatic diamine, to form an adduct suitable for dyeing and pigmenting macromolecular substances, in particular for coloring PUR-based paints, coatings and laminates.
    Type: Grant
    Filed: April 13, 1989
    Date of Patent: December 18, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Arnold Weber, Hermann Henk, Klaus Kunde, Jochen Westphal, Klaus Wunderlich
  • Patent number: 4978362
    Abstract: A thermoplastic resin composition is provided which contains a thermoplastic resin and a colorant in the form of a polyalkyleneoxy-trifluoromethyl aniline colorant provided in said thermoplastic resin in a minor amount sufficient to provide coloration to said resin, said colorant having the formula: ##STR1## wherein R.sub.1 is selected from H, a lower alkyl group containing from 1 to about 10 carbon atoms, CH.sub.2 Cl, CH.sub.2 Br, CH.sub.2 OH, phenyl or ##STR2## wherein R.sub.4 is H or a lower alkyl group containing from 1 to about 9 carbon atoms; R.sub.2 is H, CF.sub.3, a lower alkyl group containing from 1 to about 9 carbon atoms, Cl or Br; R.sub.3 is an aromatic or heteroaromatic containing group, and n is an integer from 2 to about 75.
    Type: Grant
    Filed: October 11, 1988
    Date of Patent: December 18, 1990
    Assignee: Milliken Research Corporation
    Inventors: Edward W. Kluger, John W. Rekers
  • Patent number: 4968352
    Abstract: Diaryl pigments having excellent dried ink transparency and improved process heat stability are prepared by carrying out the coupling of a bisdiazotized substituted 4,4' diaminobiphenyl with acetoacetanilides and/or pyrazolinones in the presence of an added quantity of one or more substituted aromatic amines containing at least one sulfonic or carboxylic acid substituent, or their salts. The pigments exhibit improved tolerance to variations in drying temperatures and to high drying temperatures, and have improved transparency when present in dried ink formulations.
    Type: Grant
    Filed: April 28, 1988
    Date of Patent: November 6, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Boyd A. Keys, John T. Ouderkirk
  • Patent number: 4965346
    Abstract: The novel dyes of the general formula I ##STR1## where X is hydrogen or C.sub.1-C.sub.4 -alkyl or is phenyl which is unsubstituted or substituted by fluorine, chlorine, bromine, methyl, methoxy or nitro, Y is cyano, a carboxylic ester group or nitro, Z is cyano, acetyl, benzoyl or unsubstituted or substituted carbamyl, or X and Z or Y and Z may simultaneously be a carboxylic ester group, and R.sup.1 and R.sup.2 independently of one another are each hydrogen or unsubstituted or substituted alkyl or aryl, are very useful for dyeing polyesters, polyester/cellulose blends or thermoplastics.
    Type: Grant
    Filed: March 16, 1989
    Date of Patent: October 23, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Johannes Dehnert, Gunther Lamm, Hermann Loeffler
  • Patent number: 4965345
    Abstract: Solvent dyes of the formula ##STR1## where ##STR2## R.sup.1 and R.sup.2 are each, independently of the other, hydrogen, methyl, ethyl, methoxy or ethoxy,n is 0 or 1 andk, if n is 0, is the radical of a coupling component of the pyrazolone series or, if n is 1, is the radical of a coupling component of the pyrazolone, 2-naphthol, hydroxyquinoline, aniline, naphthylamine, pyridone or 2,6-diaminopyridine series,R.sup.3 and R.sup.4 each independently of the other being C.sub.1 -C.sub.22 -alkyl which may be substituted or interrupted by oxygen, imino or C.sub.1 -C.sub.4 -alkylimino, subject to the proviso that COR has more than 8 carbon atoms, are very highly suitable for coloring organic substrates.
    Type: Grant
    Filed: October 2, 1987
    Date of Patent: October 23, 1990
    Assignee: BASF Aktiengesellschaft
    Inventor: Hermann Loeffler
  • Patent number: 4962190
    Abstract: Polyethyleneimine-containing azo dyes of the formula[(D-N=N-K-).sub.y X-].sub.m PwhereD is the radical of a diazo component which is derived from an isocyclic aromatic amine or from a heteroaromatic amine and is free of hydroxysulfonyl groups,K is the radical of a coupling component of the hydroxynaphthalene, aminopyridine or pyrazolone series which has at most one hydroxysulfonyl group, or is the radical of a coupling component derived from acetoacetic acid,y is 1 or 2,X is a covalent bond or a bridge member if y is 1 or a bridge member if y is 2, andP is the radical of a polyethyleneimine whose degree of polymerization n is from 5 to 25000,and the number m of chromophore radicals is dependent upon the degree of polymerization n and is defined by the ratio m:n=from 1:1 to 1:35, with the proviso that when K is substituted by hydroxysulfonyl the ratio m:n is from 1:2 to 1:35, are useful for dyeing or printing fiber materials and for preparing inks for the ink jet process.
    Type: Grant
    Filed: November 21, 1988
    Date of Patent: October 9, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Udo Mayer, Friedrich-Wilhelm Raulfs
  • Patent number: 4960874
    Abstract: Compounds of the general formula I ##STR1## where R is alkyl or unsubstituted or substituted aryl and K is a radical of the formula ##STR2## B is C.sub.1 -C.sub.4 -alkyl or substituted amino, R.sup.1 is hydrogen, methyl, methoxy or ethoxy, R.sup.2 and R.sup.3 independently of one another are each unsubstituted or substituted alkyl, R.sup.3 may furthermore be hydrogen, R.sup.4 is a radical of the formula --A--OCO--Y--R, Z is hydrogen or methyl, X is hydrogen, methyl, methoxy, chlorine or acylamino, A is C.sub.2 - or C.sub.3 -alkylene and Y is --O-- or --NH--, are very useful for dyeing cellulose esters and synthetic polyesters.
    Type: Grant
    Filed: July 1, 1988
    Date of Patent: October 2, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Udo Bergmann, Johannes D. Dix, Guenter Hansen, Ernst Schefczik, Guenther Seybold
  • Patent number: 4960873
    Abstract: Isothiazoleazo dyes I ##STR1## where R.sup.1 is H, halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy and A is the radical of a coupling component are used predominantly as disperse dyes for dyeing hydrophobic organic fibers and fiber materials.
    Type: Grant
    Filed: March 9, 1989
    Date of Patent: October 2, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Guenter Hansen, Gunther Lamm, Helmut Reichelt, Ernst Schefczik
  • Patent number: 4954133
    Abstract: Compounds of the formula ##STR1## wherein each A, independently, is a ##STR2## wherein R.sub.1 is hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,R.sub.2 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, --NHCONH.sub.2 or --NHCOC.sub.1-4 alkyl,R.sub.3 is hydrogen or methoxy, andm is 0, 1 or 2,each B, independently, is a radical of a diazo or coupling component, and a and each b, independently, are 0 or 1,and metal complexes thereof, which compounds or complexes are in free acid or salt form, and mixtures thereof with a compound of the formula ##STR3## or a metal complex thereof, wherein A and b are as defined above and D is a radical of a diazo or coupling component of the benzene or 1-naphthalene series are useful for dyeing and printing hydroxy group- or nitrogen-containing organic substrates, especially cellulose fibre-containing textiles (e.g., cotton), paper and leather.
    Type: Grant
    Filed: February 12, 1986
    Date of Patent: September 4, 1990
    Assignee: Sandoz Ltd.
    Inventor: Max Oppliger