Amine Salt Patents (Class 534/728)
  • Patent number: 5049238
    Abstract: A method of dyeing paper utilizing dyes suitable for dyeing paper in blue shades having the formula ##STR1## wherein R is hydrogen, --OH, --OR.sup.1 , --NH.sub.2, NHR.sup.1, --NHCOR.sup.1, --NHSO.sub.2 R.sup.1, --NHCONH.sub.2 or --NHCONHR.sup.1, in which R.sup.1 is unsubstituted alkyl or alkyl substituted by C.sub.1 -C.sub.4 -alkoxy, hydroxy-substituted C.sub.1 -C.sub.4 -alkoxy, phenyl, phenoxy or phenylcarbamoyl, in each instance the phenyl moiety being unsubstituted or substituted by C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxy or phenoxy, R.sup.1 is also unsubstituted phenyl or naphthyl or phenyl or naphthyl which is substituted by sulfo, carboxy, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, nitro, C.sub.1 -C.sub.4 -alkylcarbonylamino or C.sub.1 -C.sub.4 -alkoxycarbonylamino;X, each independently of the other, is hydrogen, unsubstituted alkyl or alkoxy or alkyl or alkoxy which is substituted by C.sub.1 -C.sub.4 -alkoxy, hydroxy-substituted C.sub.1 -C.sub.
    Type: Grant
    Filed: July 19, 1989
    Date of Patent: September 17, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Adolf Kaser
  • Patent number: 5047516
    Abstract: An azo compound of the formula: ##STR1## wherein R is an non-hydrophilic aliphatic or cycloaliphatic group containing from 8 to 40 carbon atoms;m is 0 or 1;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.The compound has non-linear optical properties which make it suitable for use in an optical element such as a waveguide, for altering the characteristics of light passing through the element.
    Type: Grant
    Filed: May 5, 1988
    Date of Patent: September 10, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Simon Allen, Paul F. Gordon
  • Patent number: 5043257
    Abstract: Azo dyes of the formula ##STR1## where X is alkyl or alkoxy each of 1 to 4 carbon atoms or halogen, X' is hydrogen, alkyl or alkoxy each of 1 to 4 carbon atoms or halogen, Y and Y' are independently of each other hydrogen or halogen, Z is hydrogen, alkyl or alkoxy or alkylthio each of 1 to 4 carbon atoms, or halogen, M is a 1-, 2- or 3-valent metal cation, ammonium or an organic ammonium compound, m is 1, 2 or 3 and n is 2 to 10, are suitable for use as image dyes in photographic silver dye bleach materials.The dyes of the invention can also be used to dye textile materials.
    Type: Grant
    Filed: December 8, 1989
    Date of Patent: August 27, 1991
    Assignee: Ilford Limited
    Inventors: Kurt Baettig, Gerald C. Jan
  • Patent number: 5041539
    Abstract: The invention relates to a process for the preparation of concentrated storage-stable aqueous solutions of yellow azo- and azoxystilbene dyes which are obtained by self-condensation of 4-nitrotoluene-2-sulfonic acid in the presence of an alkali metal hydroxide, by converting the sparingly soluble alkali metal salt of the dye into a water-soluble ammonium salt by double cation exchange via a lipophilic ammonium salt, which process comprises carrying out the double ion exchange in a two-phase system of nitrobenzene/water and using, for the first ion exchange a di- or trialkylamine containing a total of 12 to 40 carbon atoms and, for the second ion exchange, a mono-, di- or trialkanolamine containing 2 to 4 carbon atoms in each alkyl moiety.The concentrated storage-stable dye solutions so obtained are particularly suitable for dyeing paper.
    Type: Grant
    Filed: June 19, 1989
    Date of Patent: August 20, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Paul Herzig, Jurgen Markert
  • Patent number: 5026830
    Abstract: Process for the preparation of azo 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 in which the hydroxyl group is attached to K in a position adjacent to the azo group, X is hydrogen or nitro and M is an alkali metal ion or ammonium ion, which comprises coupling a diazo component of the formula ##STR2## in the presence of an alkali metal chloride and ammonium chloride with a coupling component of the formula (3) ##STR3## K and X in the formulae (2) and (3) being as defined under formula (1). The present invention allows the preparation of the said azodyes in high yields.
    Type: Grant
    Filed: August 29, 1988
    Date of Patent: June 25, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Horst Langfeld, Claudio Puebla, Gunter Sereinig
  • Patent number: 5013826
    Abstract: The azo dyes of the formula ##STR1## in which R.sub.1 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.10 alkyl, R.sub.2 is a group of the formula, --CN, --CON(R.sub.8)R.sub.9, --COR.sub.10, --COOR.sub.11, --SO.sub.2 R.sub.12 or --CONHNHR.sub.13, R.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.6 alkanoylamino, C.sub.1 -C.sub.10 alkoxy or phenoxy, R.sub.4 is substituted or unsubstituted C.sub.1 -C.sub.10 alkyl, R.sub.5 is C.sub.1 -C.sub.4 alkyl, R.sub.6 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.7 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.8, R.sub.9 and R.sub.13, independently of one another, are hydrogen or substituted or unsubstituted C.sub.1 -C.sub.10 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or naphthyl, R.sub.10, R.sub.11 and R.sub.12 are substituted or unsubstituted C.sub.1 -C.sub.10 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or naphthyl, X is an oxygen atom or a group of the formula --CH(R.sub.14)-- in which R.sub.14 is hydrogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: May 7, 1991
    Assignee: Ciba-Giegy Corporation
    Inventor: Harald Walter
  • Patent number: 5008379
    Abstract: Water-soluble, anionic, chromium complexes of disazo compounds, at least one of the complex-forming disazo compounds being of the formula, ##STR1## in which ##STR2## is the radical of a carboxy group-containing diazo component of the benzene or naphthalene series, the carboxy group being ortho to the azo group and the diazo component being free from other metallizable groups, andB-- is the radical of a diazo component of the benzene or naphthalene series free from metallizable substituents,which complexes contain at least one water-solubilizing group, are in free acid or salt form and are useful for dyeing and printing substrates such as natural and synthetic polyamides, polyurethanes and anodized aluminum, particularly fur-lined leather.
    Type: Grant
    Filed: October 29, 1987
    Date of Patent: April 16, 1991
    Assignee: Sandoz Ltd.
    Inventor: Herbert Holliger
  • 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: 4992495
    Abstract: Compounds of formula ##STR1## wherein a and b are each independently of the other halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, c and d are each independently of the other hydrogen, halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, and R.sup.1 is --CH.sub.3, phenyl, --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, and R.sup.2, R.sup.3, R.sub.4 and R.sub.5 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted by a chlorine atom or a --OH group, or are C.sub.7 -C.sub.9 aralkyl, C.sub.5 -C.sub.8 cycloalkyl, phenyl or phenyl which is substituted by 1 to 3 halogen atoms or methyl or methoxy groups, or is a heterocyclic radical of the benzimidazole, benzoxazole, benzthiazole or pyridine series, or R.sup.3 and R.sup.
    Type: Grant
    Filed: June 16, 1988
    Date of Patent: February 12, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Stefan Hari, Georg Cseh
  • Patent number: 4988805
    Abstract: The dyestuffs of the general formulae ##STR1## and salts thereof whereinX denotes hydrogen, alkoxy or NHR.sub.3,R denotes hydrogen, alkyl or alkoxy,R.sub.1 denotes alkyl,R.sub.2 and R.sub.3 denote hydrogen, alkyl, alkylcarbonyl, alkylsulphonyl, aryl, arylcar=bonyl, arylsulphonyl, aralkyl, aralkylcarbonyl or aminocarbonyl andm and n denote 1 or 2, andwherein the substituents mentioned can, in turn, be substituted by nonionic radicals or carboxylic or sulphonic acid groups customary in dyestuffs chemistry, are used for dyeing cellulose-containing materials and leather.
    Type: Grant
    Filed: July 14, 1988
    Date of Patent: January 29, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus Kunde
  • 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
  • Patent number: 4946508
    Abstract: Disazo pyrazolone pigments are provided which have improved properties achieved by incorporating certain azomethine compounds. The pigment is prepared by reacting a primary amine terminated alkylene oxide polymer and acetoacetanilide or substituted acetoacetanilide to form an azomethine coupler, and subsequently co-reacting the azomethine coupler and a pyrazolone coupler with tetrazotized 3,3'-dichlorobenzidine or tetrazotized o-dianisidine. The pigment is useful in printing ink, plastics and paints.
    Type: Grant
    Filed: May 23, 1989
    Date of Patent: August 7, 1990
    Assignee: Sun Chemical Corporation
    Inventors: Russell J. Schwartz, Manuel Z. Gregorio
  • Patent number: 4894447
    Abstract: Azo dyes of the formula ##STR1## or tautomeric forms thereof, in which: Z is N or CH,X is O, NR.sub.1 or N,W is N or C,K is a coupling component,R is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, nitro, --CN, --NHR.sub.1, --NH-acyl, phenoxy, --COOH, COOR.sub.1, --CONHR.sub.1 or substituted or unsubstituted phenyl, R.sub.1 being hydrogen, substituted or unsubstituted C.sub.1 -C.sub.6 -alkyl or substituted or unsubstituted phenyl,M is H.sup..sym., Li.sup..sym., Na.sup..sym., K.sup..sym., NH.sub.4.sup..sym. or the protonated form of a C.sub.4 -C.sub.12 -trialkylamine, of a C.sub.4 -C.sub.12 -diamine or of a C.sub.2 -C.sub.12 -alkanolamine,A is a carbocyclic or nitrogen-containing aromatic radical which can be further substituted, andB is a 1,4-phenylene radical which can be further substituted.
    Type: Grant
    Filed: April 9, 1987
    Date of Patent: January 16, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Jean-Marie Adam
  • Patent number: 4889846
    Abstract: The invention concerns azo compounds of formula ##STR1## or a salt thereof, in which formula R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, and R.sup.6 are each independently hydrogen or lower alkyl, R.sup.7 and R.sup.8 are each independently alkyl of 1 to 7 carbon atom or cycloalkyl of 5 to 7 carbon atoms optionally substituted by lower alkyl which possess anti-inflammatory activity.
    Type: Grant
    Filed: April 15, 1988
    Date of Patent: December 26, 1989
    Assignee: John Wyeth & Brother Limited
    Inventor: Roger Crossley
  • Patent number: 4866163
    Abstract: Compounds of the formula ##STR1## wherein each R.sub.1 is independently hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or --NHCOC.sub.1-4 alkyl, each R.sub.2 is H, halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, each R.sub.3 is independently halo, hydroxy, C.sub.1-4 alkoxy, --NHOH, amino or an aliphatic, aromatic cycloaliphatic or saturated heterocyclic amino radical, and is divalent aliphatic or aromatic group or, together with the NH radicals to which it is attached, forms a piperazine ring, and the use thereof for dyeing or printing hydroxy group- or nitrogen-containing organic substrates after which the dyed or printed substrate is optionally treated with a cationic fixing agent.
    Type: Grant
    Filed: May 2, 1984
    Date of Patent: September 12, 1989
    Assignee: Sandoz, Ltd.
    Inventor: Werner Koch
  • Patent number: 4863910
    Abstract: A complex of an azo compound of the formula ##STR1## wherein R and R' are selected from the group consisting of hydrogen, --COCR.sub.4.sup.3, --COCHR.sub.2.sup.4, --CO.sub.2 C.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 R.sup.4, --(CH.sub.2 CH.sub.2 R.sup.4)2, --CH.sub.2 CH.sub.2 OH, --CONHCH.sub.2 CH.sub.2 R.sup.4 and --CH.sub.2 CH.sub.2 OCOHN.sub.2, R.sup.4 is selected from the group consisting of chlorine, ##STR2## --NHCO.sub.2 CH.sub.2 CH.sub.2 OH, --HNCO.sub.2 C.sub.2 H.sub.5, --NHOH, --NHCONHOH and --NHCH.sub.3 ; R.sup.1 and R.sup.2 are individually selected from the group consisting of ##STR3## --NHCH.sub.2 CH.sub.2 Cl, --NHCONHOH, --NHCO.sub.2 C.sub.2 H.sub.5, 6-mercapropurin, 5-fluoruracil and prenissolin, R.sup.3 is selected from the group consisting of hydrogen, --COCHR.sub.2.sup.4, --SO.sub.2 CH.sub.3, --COC.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 R.sub.4 and --CONH.sub.2, R.sup.
    Type: Grant
    Filed: May 20, 1986
    Date of Patent: September 5, 1989
    Inventor: Takeo Takayanagi
  • Patent number: 4841037
    Abstract: A naphthalene trisazo compound represented by the general formula (I) or (II): ##STR1## wherein A and B each represents a substituted or unsubstituted benzene or naphthalene ring; m represents zero or 1; and M represents an alkali metal atom, ammonium or H.Am (wherein Am represents an amine); or ##STR2## wherein X represents a hydrogen atom, a lower alkyl group, a phenyl group or a phenyl group substituted by --SO.sub.3 M; m represents zero or 1; M represents an alkali metal atom, ammonium or H.Am (wherein Am represents an amine); A, B and C each represents a substituted or an unsubstituted benzene or naphthalene ring, provided that B and C do not represent a naphthalene ring at the same time. A recording liquid containing these compounds is suitable for use in an ink-jet recording system.
    Type: Grant
    Filed: June 10, 1986
    Date of Patent: June 20, 1989
    Assignees: Canon Kabushiki Kaisha, Mitsubishi Chemical Industries Limited
    Inventors: Tokuya Ohta, Masatsune Kobayashi, Yuko Suga, Konoe Miura, Hiroshi Takimoto, Tomio Yoneyama
  • Patent number: 4833235
    Abstract: Disazo compounds of the formula ##STR1## and salt thereof, D is the radical of a diazo component of the benzene or naphthalene series.K is the radical of a heterocyclic coupling component of the aminopyrazole-, pyridone- or barbituric acid-series, n is 1 to 4,R.sub.1 is hydrogen, C.sub.1-4 alkyl or substituted C.sub.1-4 alkyl,each of R.sub.2 and R.sub.3 is independently hydrogen, halo, C.sub.1-4 alkyl, substituted C.sub.1-4 alkyl, C.sub.1-4 alkoxy, substituted C.sub.1-4 alkoxy, --NHCO--Rhd 5, amino, substituted amino or a quaternary ammonium group, wherein R.sub.5 is C.sub.1-4 alkyl, substituted C.sub.1-4 alkyl, C.sub.1-4 alkoxy or amino,R.sub.4 is hydrogen, C.sub.1-4 alkyl, C.sub.
    Type: Grant
    Filed: October 7, 1987
    Date of Patent: May 23, 1989
    Assignee: Sandoz Ltd.
    Inventor: Reinhard Pedrazzi
  • Patent number: 4780532
    Abstract: A water-soluble dye, free from cellulose reactive groups, of the formula: ##STR1## wherein R.sup.1 is --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H,R.sup.2 is H or --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H, orR.sup.1 & R.sup.2 together with the nitrogen atom form a morpholine ringa & b are different and from 1 to 8m is from 1 to 10;n is from 0 to 9;q is 1/2 or 1p is 1 or 2L is a transition metal capable of complexing with a dyeM is H, ammonium, or a monovalent metal;B, D, F & E are H or substituents;X is NR.sup.1 R.sup.2, NR.sup.3 R.sup.4, --NR.sup.3 --Z--NR.sup.4 --, OR.sup.3, or the residue of a mono- or dis-azo chromophore comprising benzene, naphthalene or hetero-mono- or bi-cyclic diazo and coupling components, linked to the triazine nucleus through a primary or secondary amino linking group in which R.sup.3 and R.sup.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: October 25, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
  • Patent number: 4769447
    Abstract: The present invention provides gamma-glutamyl-4-azoanilides, processes for their preparation and their use as substrates for gamma-glutamyl transferase determination, of the formula ##STR1## wherein X is alkyl, --(CH.sub.2).sub.m --COOH or --O--(CH.sub.2).sub.n --COOH wherein m is 0-4 and n is 1-4; R is optionally substituted p-nitrophenyl; an optionally substituted thiophene residue; an optionally substituted thiazole residue; an optionally substituted benzothiazole residue; an optionally substituted benzoisothiazole residue; an N-alkylthiazole residue; or an optionally substituted 1,3,5-thiodiazole residue; as well as the alkali metal, alkaline earth metal and ammonium salts thereof.
    Type: Grant
    Filed: January 27, 1987
    Date of Patent: September 6, 1988
    Assignee: Boehringer Mannheim GmbH
    Inventors: Elli Rauscher, John Griffiths, Leonard F. Dixon
  • Patent number: 4764599
    Abstract: Sulfo-free compounds of the formula ##STR1## where R is hydrogen or C.sub.1 -C.sub.4 -alkyl andK.sup.1 and K.sup.2 independently of one another are a radical of a coupling component, and the rings A and B may furthermore be monosubstituted or polysubstituted by fluorine, chlorine, bromine, nitro, methyl, trifluoromethyl, ethyl, acetyl, benzoyl, a carboxylic ester group, unsubstituted or substituted carbamyl or sulfamyl, an aryl sulfonate group, C.sub.1 -C.sub.4 -alkylsulfonyl, unsubstituted or substituted phenylsulfonyl, cyano or acylamino or a fused ring, are very useful as pigments for coloring printing inks, surface coatings or plastics.
    Type: Grant
    Filed: September 30, 1986
    Date of Patent: August 16, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Colberg, Erwin Hahn
  • Patent number: 4750936
    Abstract: Stabilized, aqueous dispersions of multivalent metal humates are disclosed as a compatible and functional component in printing ink formulations.
    Type: Grant
    Filed: January 27, 1987
    Date of Patent: June 14, 1988
    Assignee: Union Camp Corporation
    Inventors: James C. West, William C. Firth, Jr.
  • Patent number: 4749784
    Abstract: The specification describes a new group of alkanol substituted disazo compounds that are useful in dyeing polyamide textile fibers in orange hues. The new compounds are compatible with several acid blue dyes and several acid red dyes that are commercially important as dyes for nylon. The new compounds are particularly well suited for use as the "yellow" component in trichromatic systems for dying polyamide carpeting and other textiles. The new compounds are relatively inexpensive to make and have outstanding application and fastness properties. Other aspects of the specification are concerned with a method of making the new compounds and with a method of dyeing polyamides with said compounds and to the novel dyed polyamides resulting from the use of the new group of compounds as dyes.
    Type: Grant
    Filed: February 10, 1987
    Date of Patent: June 7, 1988
    Assignee: Crompton & Knowles Corporation
    Inventors: James F. Feeman, Jay E. Rowe
  • Patent number: 4746733
    Abstract: A water-soluble dye, free from cellulose reactive groups, of the formula: ##STR1## wherein R.sup.1 is --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H;R.sup.2 is H or --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H; orR.sup.1 & R.sup.2 together with the nitrogen atom form a morpholine ring;a & b are different and from 1 to 8;m is from 1 to 10;n is from 0 to 9;Y is a triphendioxazinylene (TPD) group;M is H, ammonium, or a metal;X is NR.sup.1 R.sup.2, alkoxy, NR.sup.3 R.sup.4 in which R.sup.3 and R.sup.4 are each independently selected from H, alkyl, aryl and heteroaryl, or the residue of a mono- or dis-azo chromophore comprising benzene, naphthalene or mono- or bi-cyclic heteroaryl diazo and coupling components, linked to the triazine nucleus through a primary or secondary amine linking group;andZ is an alkylene, arylene or aralkylene group,suitable for the preparation of a printing ink, especially for ink jet printing.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: May 24, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
  • Patent number: 4737240
    Abstract: Black trisazo dyes for cellulosic textiles, leather and especially paper having the structure ##STR1## where A is ##STR2## one of B.sub.1 and B.sub.2 is hydrogen and the other is --SO.sub.3 M or a mixture thereof, and M is hydrogen, sodium, potassium, lithium or --HNR.sub.1 R.sub.2 R.sub.3 wherein R.sub.1, R.sub.2 and R.sub.3 represent the same or different substituents selected from hydrogen, lower alkyl and lower hydroxyalkyl, and stable liquid concentrates of these dyes are described.
    Type: Grant
    Filed: June 27, 1986
    Date of Patent: April 12, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Herbert S. Davis, Roy E. Smith, Mortimer Weiser
  • Patent number: 4725676
    Abstract: The present invention is concerned with azo compounds having the structure ##STR1## in which: Y is hydrogen, andX and Z are carboxy or lower alkoxycarbonyl,or the lactones or salts of said azo compound, such compounds being useful in pharmaceutical compositions and being specifically useful to inhibit 15-prostaglandin dehydrogenase (PGDH).
    Type: Grant
    Filed: July 3, 1986
    Date of Patent: February 16, 1988
    Assignee: Pharmacia AB
    Inventors: Karl H. Agback, Alf S. Nygren
  • Patent number: 4703113
    Abstract: A water-soluble dye, free from cellulose reactive groups, of the formula: ##STR1## wherein R.sup.1 is --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H,R.sup.2 is H or --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H, orR.sup.1 & R.sup.2 together with the nitrogen atom form a morpholine ringa & b are different and from 1 to 8m is from 1 to 10;n is from 0 to 9;M is H, ammonium, or a monovalent metal;X (i) NR.sup.1 R.sup.2, (ii) NR.sup.3 R.sup.4, in which R.sup.3 and R.sup.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: October 27, 1987
    Assignee: Imperial Chemical Industries PLC
    Inventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
  • Patent number: 4694075
    Abstract: The compounds of the formula ##STR1## where Y is hydrogen, chlorine, bromine or nitro, Z is hydrogen, chlorine, bromine, a sulfonic ester group or unsubstituted or substituted sulfamyl, X is --O-- or ##STR2## R is alkylene which may or may not be interrupted by oxygen or ##STR3## m is 0 or 1, p is 1 or 2, R.sup.1 and R.sup.2 independently of one another are each hydrogen, unsubstituted or substituted alkyl, alkenyl, cycloalkyl, aralkyl, or aryl, or R.sup.1 and R.sup.2 together with the nitrogen form a heterocyclic structure, R.sup.3 is hydrogen or unsubstituted or substituted alkyl, R.sup.6 and R.sup.7 independently of one another are each hydrogen, unsubstituted or substituted alkyl, alkoxy or acylamino, K is a radical of a coupling component, A.crclbar. is an anion, R.sup.4 is unsubtituted or substituted alkyl and R.sup.5 is hydrogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: January 21, 1986
    Date of Patent: September 15, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Colberg, Erwin Hahn
  • Patent number: 4686285
    Abstract: (i) Metal-free compounds of the formula ##STR1## (ii) tautomers thereof, (iii) 1:1 and 1:2 metal complexes of (i) and (ii),(iv) salts of (i), (ii), and (iii), and(v) mixtures of (i), (ii), (iii), and (iv),wherein the symbols are as defined in the Specification, are useful as dyes for, for example, polymers and copolymers of acrylonitrile, polyesters modified to contain acid groups, polyamides such as wool, leather, cotton, bast fibers such as hemp, flax, sisal jute, coir and straw, regenerated cellulose, glass fibers and paper (those wherein R.sub.o is other than hydrogen) or as intermediates for the synthesis of dyes.
    Type: Grant
    Filed: February 8, 1985
    Date of Patent: August 11, 1987
    Assignee: Sandoz Ltd.
    Inventor: Reinhard Pedrazzi
  • Patent number: 4670547
    Abstract: Tetrakisazo compounds of the formula ##STR1## and salts thereof, whereinB is ##STR2## wherein B.sub.1 is a bridging radical as defined in the specification,R.sub.7 is hydrogen or C.sub.1-4 alkyl,R.sub.8 is hydrogen or C.sub.1-4 alkyl, andeach Y is independently halo, hydroxy, amino, hydroxyamino, C.sub.1-4 alkoxy, phenoxy, substituted phenoxy, an aliphatic, cycloaliphatic or aromatic amine radical or a saturated heterocyclic amine radical,each D is independently mono-, di- or tri-sulfonaphthyl or ##STR3## wherein R.sub.2 is hydrogen, halo, carboxy, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy, --COOR.sub.4, (C.sub.1-4 alkyl)carbonylamino or (C.sub.1-4 alkoxy)carbonylamino, wherein R.sub.4 is C.sub.1-4 alkyl, phenyl, benzyl or phenyl or benzyl substituted by 1 or 2 substituents selected from halo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy,R.sub.3 is hydrogen, halo, hydroxy, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, andm is 0, 1 or 2,each M is independently ##STR4## wherein R.sub.5 is hydrogen, halo, C.sub.
    Type: Grant
    Filed: November 8, 1984
    Date of Patent: June 2, 1987
    Assignee: Sandoz Ltd.
    Inventor: Friedrich Lehr
  • Patent number: 4668774
    Abstract: Novel dye salts of anionic dyes of the general formula I ##STR1## where F is a radical of an anionic dye, n is 1, 2, 3 or 4, and B.sup.1 and B.sup.2 independently of one another are each unsubstituted or substituted branched alkyl or alkyl-substituted cycloalkyl having a total of 10 to 36 carbon atoms, are very useful for dyeing solvents, printing inks or polymeric film-forming materials.
    Type: Grant
    Filed: April 23, 1985
    Date of Patent: May 26, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Hermann Loeffler, Rainer Dyllick-Brenzinger
  • Patent number: 4656256
    Abstract: Compounds of the formula ##STR1## where Y is chlorine or bromine, Z is hydrogen, chlorine, bromine, a sulfonic ester group, nitro or unsubstituted or substituted sulfamyl, X is --O-- or ##STR2## R is alkylene which may or may not be interrupted by oxygen, ##STR3## m is 1 or 2, n is 0 or 1, p is 0, 1 or 2, q is 1 or 2, R.sup.1 and R.sup.2 independently of one another are each hydrogen, unsubstituted or substituted alkyl, alkenyl, cycloalkyl, aralkyl or aryl, or R.sup.1 and R.sup.2, together with the nitrogen atom, form a heterocyclic structure, R.sup.3 is hydrogen or unsubstituted or substituted alkyl, B is hydrogen or C.sub.1 -C.sub.4 -alkyl, B.sup.1 is hydrogen, hydroxyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkyl, A.sup.- is an anion, R.sup.4 is unsubstituted or substituted alkyl, R.sub.5 is hydrogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: May 16, 1985
    Date of Patent: April 7, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Colberg, Hans-Juergen Degen, Johannes P. Dix
  • Patent number: 4652632
    Abstract: Naphtholazo benzoylalkylene amines and salts thereof which are useful as dyes for acid-modified fibers, leather and paper, and which are represented by the formula ##STR1## wherein n is 0 or 1,A is an anion,R is C.sub.2 - to C.sub.4 -alkyleneR.sup.1 and R.sup.2 independently of one another are C.sub.1 - to C.sub.4 -alkyl, methoxyethyl, cyclohexyl, and R.sup.1 and R.sup.2 together are ##STR2## and R.sup.3 is methyl, ethyl or hydroxyethyl.
    Type: Grant
    Filed: April 1, 1985
    Date of Patent: March 24, 1987
    Assignee: BASF Aktiengesellschaft
    Inventor: Horst Colberg
  • Patent number: 4628082
    Abstract: Azobarbituric acid derivatives characterized in that in their free acid form they have the following tautomeric structure are disclosed: ##STR1## The azobarbituric acid derivatives are characterized in that X and Y rings can each carry one or two substituents from the series comprising .dbd.O, .dbd.S, .dbd.NR.sub.7, --NR.sub.6 R.sub.7, --OR.sub.6, --SR.sub.6, --COOR.sub.6, --CN, --CONR.sub.6 R.sub.7, --SO.sub.2 R.sub.8, ##STR2## alkyl, cycloalkyl, aryl and aralkyl, the total number of the endocyclic and exocyclic double bonds for each of the rings X and Y being three.The new azobarbituric acid derivatives are other than those of azobarbituric acid, azouracil and uracil-5-azobarbituric acid and their salts. The compounds are useful as pigments which pigments are useful for pigmented paints, in printing inks, distempers or emulsion paints, inter alia.
    Type: Grant
    Filed: May 14, 1985
    Date of Patent: December 9, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Lorenz, Karl H. Schundehutte
  • Patent number: 4622391
    Abstract: New inclusion compound, intercalation compounds or solid solutions which are the nickel salts or nickel complexes of a compound which, in one of its tauteromeric structures, corresponds to the formula ##STR1## which contain at least one other included compound, except for one composition of matter which consists of 45 to 82% by weight of azobarbituric acid/nickel 1:1 complex, 3 to 15% by weight of benzene-sulphonamide, 5 to 20% by weight of nickel acetate and 10 to 20% by weight of water and the use of these materials as pigments are disclosed.
    Type: Grant
    Filed: May 15, 1985
    Date of Patent: November 11, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Lorenz, Karl H. Schundehutte
  • Patent number: 4618674
    Abstract: Red monoazo dyestuffs from diazotized 1-aminobenzonitrile or 1-amino-4-, 5- or 6-halo-benzonitrile and 2-amino-8-hydroxynaphthalene-6-sulfonic acid. These dyes are particularly distinguished by their good migration and leveling properties and excellent fastness to light. Said dyestuffs are moreover suitable for obtaining very even combination dyeings together with known blue, yellow and orange acid dyestuffs. These dyestuffs are particularly suited for the dyeing of carpeting, upholstery fabrics and drapery materials.
    Type: Grant
    Filed: December 30, 1983
    Date of Patent: October 21, 1986
    Inventor: Kurt A. Dellian
  • Patent number: 4617380
    Abstract: A process is disclosed for the preparation of concentrated stable liquid dye solutions of CI Direct Yellow 11 starting with the tetrasodium complex of the stilbeneazo(xy) based-catalyzed condensation of 4-nitro-toluene-2-sulfonic acid, the wet-cake or the dried technical grade of the condensed tetrasodium complex. The process comprises the steps of forming an aqueous suspension of the starting materials which are admixed with the extended surface silica filter aid and the resulting slurry is acidified with a strong inorganic acid to pH below about 2.
    Type: Grant
    Filed: September 11, 1984
    Date of Patent: October 14, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: James W. Hinson, Jo A. Cleverdon
  • Patent number: 4617381
    Abstract: A process is disclosed for the preparation of concentrated stable liquid dye solutions of CI Direct Yellow 11 starting with the product of the basic condensation of para-nitrotoluene-ortho-sulfonic acid in the form of its tetrasodium reaction mass or the wet filter cake separation of the solids from said mass and the reaction liquids or the dry technical grade sodium complex which is the dried filter cake. The solid starting material is suspended in a lower alkanol/water medium; the suspension is acidified to a pH below about 2.5 to acidify each sulfo moiety on the chromophore and to form the free inorganic salt; this acidified suspension is heated to assure completion of the metathetical salt-forming reaction; after sufficient heating, the mixture of the acidified chromophore and the salt is neutralized to a pH in the range 6.0 to 7.
    Type: Grant
    Filed: September 11, 1984
    Date of Patent: October 14, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: James W. Hinson, Jo A. Cleverdon
  • Patent number: 4594410
    Abstract: Azo dyes of the formula ##STR1## and external salts thereof, wherein F is the residue of a monoazo or disazo compound in 1:1 metal complex form or of a trisazo, disazoazoxy or tetrakisazo compound in metal-free or 1:1 metal complex form,each X is independently --NR.sub.2 --Q--NR.sub.3 R.sub.4 or --NR.sub.2 --Q--N.sup..sym. R.sub.5 R.sub.6 R.sub.7,whereinQ is linear or branched C.sub.2-6 alkylene or --NH--CO--CH.sub.2 --,R.sub.2 is hydrogen or C.sub.1-4 alkyl,each of R.sub.3 and R.sub.4 is independently hydrogen; C.sub.1-6 alkyl; C.sub.2-6 alkyl monosubstituted by cyano or hydroxy in the 2-, 3-, 4-, 5- or 6-position; phenyl(C.sub.1-3 alkyl); phenyl(C.sub.1-3 alkyl) having, on the phenyl ring, 1, 2 or 3 substituents selected from chloro, C.sub.1-4 alkyl and C.sub.1-4 alkoxy; C.sub.5-6 cycloalkyl or C.sub.5-6 cycloalkyl substituted by 1, 2 or 3 C.sub.1-4 alkyl groups or --NR.sub.3 R.sub.
    Type: Grant
    Filed: August 18, 1982
    Date of Patent: June 10, 1986
    Assignee: Sandoz Ltd.
    Inventor: Reinhard Pedrazzi
  • Patent number: 4593087
    Abstract: Disclosed are azo dyes containing diazonium moieties from aminothiazoles, aminoisothiazoles, or aminothiadiazoles (1,2,4- or 1,3,4-), and certain coupler moieties from aniline, tetrahydroquinoline, and benzomorpholine type compounds, wherein the diazonium moieties have at least one cinnamoyl group, and wherein a wide variety of groups, e.g., one or more water-solubilizing substituents such as sulfonic acid groups or their metal or amine salts may be present in the dye molecule. These dyes are useful for dyeing materials selected from polyamide, cellulose ester, polyester, wool and other natural and synthetic fibers and generally exhibit improvements in dyeability and fastness properties.
    Type: Grant
    Filed: January 23, 1984
    Date of Patent: June 3, 1986
    Assignee: Eastman Kodak Company
    Inventor: Robert N. Gourley
  • Patent number: 4581445
    Abstract: There are described novel cationic benzothiazole disazo compounds of the formula ##STR1## K independently of one another are each a coupling component, R independently of one another are each an unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl group,R.sub.1 independently of one another are each hydrogen, unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted C.sub.1 -C.sub.4 -alkoxy, or halogen,X is the direct bond, --(CH.sub.2).sub.y wherein y is a number from 1 to 4, --CH.dbd.CH--, a phenylene group, a naphthylene group, a heterocyclic radical, an --NH-alkylene-(C.sub.1 -C.sub.6)--NH-- radical or an --NH-arylene-NH-- radical, andAn is an anion, with the proviso that when the coupling component K is a dimethylaminophenyl radical, the divalent bridge member X is not the --(CH.sub.2).sub.2 -- group are useful for dyeing and printing textile materials, leather and in particular paper. The dyeings obtained have good fastness properties, especially good fastness on paper to light.
    Type: Grant
    Filed: September 16, 1983
    Date of Patent: April 8, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Visvanathan Ramanathan
  • Patent number: 4562249
    Abstract: There are described novel yellow to red azo compounds of the formula I ##STR1## wherein each D independently of the other is the radical of an aromatic or heterocyclic diazo component, each Z independently of the other is hydrogen or a C.sub.1 -C.sub.4 -alkyl group or an acylamino group, Y is hydrogen or an unsubstituted or substituted C.sub.1 -C.sub.6 -alkyl group, X is either the direct bond or C.sub.1 -C.sub.6 -alkylene, ##STR2## and n is a number from 2 to 6, preferably 2; and the substituent Y, in the case of an unsubstituted or substituted C.sub.1 -C.sub.6 -alkyl group, can also be bonded to the o-position relative to the N atom of the phenylene group to form a six-membered ring, or both Y substituents can be linked together to form a C.sub.1 -C.sub.
    Type: Grant
    Filed: March 5, 1985
    Date of Patent: December 31, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Hansrudolf Schwander, Rudolf Hurter
  • Patent number: 4560745
    Abstract: A process for the preparation of dyes which contain sulfonic acid groups and have a low electrolyte content, wherein an aqueous solution or suspension, which may or may not contain inorganic salts, of the dye containing sulfonic acid groups is(a) mixed with an amount, equivalent to the said dye, of a non-emulsifying, water-insoluble amine of a total of 12 to 40 carbon atoms, which forms, with the said dye, a salt which is sufficiently lipophilic for it to separate spontaneously from the aqueous phase,(b) the pH is brought to <5 with an acid and the batch is mixed thoroughly,(c) the two resulting phases of different density are separated, and(d) the phase which consists of the lipophilic ammonium salt of the dye is mixed, with or without prior washing with water, with a water-soluble base whose sulfonate salt is to be prepared, and with water, the resulting phases are separated, and the salt is left in the aqueous solution or is isolated therefrom.
    Type: Grant
    Filed: May 12, 1981
    Date of Patent: December 24, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Volkmar Weberndoerfer, Friedrich Brunnmueller, Manfred Eisert, Rudolf Bermes
  • Patent number: 4554348
    Abstract: Disclosed are new acid azo dyes prepared from 2-amino-cinnamoylthiophene compounds. These dyes give bright red to blue shades, for example, on polyester, cellulose acetate, wool and particularly polyamide fibers and exhibit improvements in one or more of such properties as bathochromic shift, fastness to light, sublimation, chlorine, heat, ozone, gas, perspiration, crock, and wash, build, pH stability, bloom resistance, depth of shade, leveling, strike rate, migration, and the like. The dyes have the general formula ##STR1## wherein: R.sup.14 is H or alkyl; R is a substituent selected, for example, from alkyl, substituted alkyl, hydroxy, alkoxy, halogen, nitro, alkoxycarbonyl, alkanoyloxy, alkanoyl, cyano, alkylamino, and dialkylamino; C.sup.1 represents an aniline, tetrahydroquinoline or benzomorpholine coupling component which may be extensively substituted; each of R.sup.12 and R.sup.13 is selected from H, alkyl, alkoxy, acyl, halogen, and the like; and at least one of the water solubilizing groups, --SO.
    Type: Grant
    Filed: January 23, 1984
    Date of Patent: November 19, 1985
    Assignee: Eastman Kodak Company
    Inventor: Robert N. Gourley
  • Patent number: 4552952
    Abstract: This invention relates to azo dyes which may be unsubstituted or substituted with a variety of groups known to the dye art, and containing diazonium moieties from 2-aminobenzothiazole or 2-aminobenzisothiazole type compounds, and certain coupler moieties from aniline, tetrahydroquinoline, or benzomorpholine compounds, wherein the diazonium moieties have one or two cinnamoyl substituents, and wherein one or more water-solubilizing groups such as a sulfonic acid group or its metal or amine salt may be present as a substituent in the dye molecule for acid dyeing. These dyes are particularly useful in dyeing one or more of polyamide cellulose acetate polyester, wool and other fibers.
    Type: Grant
    Filed: January 23, 1984
    Date of Patent: November 12, 1985
    Assignee: Eastman Kodak Company
    Inventor: Robert N. Gourley
  • Patent number: 4552951
    Abstract: This invention relates to azo dyes which may be unsubstituted or substituted with a variety of groups known to the dye art, and containing a diazonium moieties from an aniline type compound and certain coupler moieties from aniline, tetrahydroquinoline, or benzomorpholine compounds, wherein the diazonium moiety has one or two cinnamoyl substituents, and wherein one or more water-solubilizing groups such as a sulfonic acid group or its metal or amine salt may be present as a substituent in the dye molecule for acid dyeing. These dyes are particularly useful in dyeing one or more of polyamide cellulose acetate polyester, wool and other fibers.
    Type: Grant
    Filed: January 23, 1984
    Date of Patent: November 12, 1985
    Assignee: Eastman Kodak Company
    Inventor: Robert N. Gourley
  • Patent number: 4536570
    Abstract: This invention relates to novel mixtures consisting essentially of benzanilide bridged disazo compounds which are randomly substituted with x (N-substituted sulfonamido) groups, to acid-addition salts of said disazo compounds, useful as direct dyes particularly in the dyeing of cellulose, and to methods of preparation of said mixtures of (N-substituted sulfonamido) substituted disazo compounds.
    Type: Grant
    Filed: October 25, 1982
    Date of Patent: August 20, 1985
    Assignee: The Hilton-Davis Chemical Co.
    Inventor: Nathan N. Crounse
  • Patent number: 4483796
    Abstract: Disazo and polyazo compounds of the formula ##STR1## wherein each A is independently ##STR2## and each R.sub.3 is independently C.sub.1-4 alkyl, oreach A, R.sub.3 and the ##STR3## radical to which they are attached, taken together, independently, are ##STR4## wherein each R.sub.21 is independently halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,p is 0, 1 or 2,the * denotes the carbon atom attached to the --N.dbd.N-- radical, andthe ** denotes the carbon atom attached to X,each R.sub.1 and the ##STR5## radical to which it is attached taken together, independently, are the radical of an aromatic or heterocyclic coupling component,each A.sub.1 and A.sub.2 taken together are --O--Me--O--, wherein Me is copper, cobalt, iron, nickel, manganese or zinc, oreach A.sub.1 is hydroxy, andeach A.sub.2 is independently hydrogen, hydroxy or C.sub.1-4 alkoxy,X is a direct bond or a bridging radical,each Y is independently a direct bond, C.sub.1-4 alkylene, --CO--NH--(CH.sub.2).sub.m --, --NH--CO--(CH.sub.2).sub.m -- or --SO.sub.
    Type: Grant
    Filed: August 18, 1982
    Date of Patent: November 20, 1984
    Assignee: Sandoz Ltd.
    Inventors: Paul Doswald, Emil Moriconi, Helmut Moser, Horst Schmid