Plural Sulfonic Acid Groups Patents (Class 534/784)
  • Publication number: 20130227797
    Abstract: The invention relates to the dyeing of human keratinous fibres, in particular the hair, using anionic direct dyes or acid dyes having a tetraalkylammonium counterion of formula (I) with Col(?)m. R1, R2, R3, R4, m, and n as defined in the description. A subject-matter of the invention is a dyeing composition comprising an anionic dye of formula (I) and a method for dyeing keratinous fibres, such as the hair, employing the said composition. A subject-matter of the invention is likewise novel dyes of formula (I) and their uses for the colouring of keratinous fibres. This composition makes it possible to obtain a chromatic, powerful and particularly persistent colouring on keratinous fibres.
    Type: Application
    Filed: November 16, 2011
    Publication date: September 5, 2013
    Applicant: L'OREAL
    Inventor: Andrew Greaves
  • Patent number: 7341607
    Abstract: The present invention relates to novel yellow anionic dyes, a process for their preparation, certain novel intermediates for their preparation and the use of these dyes for dyeing natural or synthetic materials, in particular, paper.
    Type: Grant
    Filed: May 27, 2003
    Date of Patent: March 11, 2008
    Assignee: Ciba Specialty Chemicals Corp.
    Inventors: Michael Lennartz, Adolf Käser, Sandra Weiss
  • Patent number: 6913640
    Abstract: Novel improved single-phase mixed crystals of monoazo dyes laked with alkaline earth metal cations and ammonium cations in a molar ratio of about 1:2 having a fine particle size and substantially better fastness properties than similar known products are excellently suitable as tinctorially strong pigments. Also claimed is a process for the preparation of a single-phase mixed crystal pigment of formula wherein E is Mg, Ca or Sr, by crystallisation from an inert hydrophilic liquid in the presence of solvated catiens E++, NR5R6R7R8+, x is a number from 0.33 to 0.62 and y is a number from 0.76 to 1.34, and the concentration of solvated catiens E++ at the beginning of the crystallisation is higher than the concentration of solvated cations NR5R8R7R8+.
    Type: Grant
    Filed: January 15, 2002
    Date of Patent: July 5, 2005
    Assignee: CIBA Specialty Chemicals
    Inventors: Philippe Bugnon, Carolin Sansonnens, Greig Chisholm
  • Patent number: 6784286
    Abstract: The invention relates to pyrazolone pigments of general formula (I), wherein the radicals R1, R2, R3 and R4 independently represent hydrogen, chlorine, methyl or ethyl, whereby at least one of the radicals R1-R4 is different from hydrogen. The inventive pigments are characterised by a CIELAB colour angle of 80-85°, a chroma of 58-62 and a luminosity ≧87 (measuring angle 45°, standard illuminant D65).
    Type: Grant
    Filed: June 13, 2003
    Date of Patent: August 31, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Blaschka, Günter Smeyts, Paul Günthert
  • Publication number: 20040087781
    Abstract: Novel improved mixed crystals of monoazo dyes of formula (I), wherein R1 is methyl or chlorine, and R2, R3 and R4 are each independently of the others hydrogen, methyl or chlorine, which dyes have been laked with alkaline earth metal cations and ammonium cations in a molar ratio of about 1:2. The mixed crystals are single-phase. The products according to the invention, while having a fine particle size, exhibit substantially better fasteness properties than similar known products and are therefore excellently suitable as tinctorially strong pigments. In addition, the part played by after-treatment is less critical.
    Type: Application
    Filed: December 23, 2003
    Publication date: May 6, 2004
    Inventors: Philippe Bugnon, Caroline Sansonnens, Greig Chisholm
  • Patent number: 6613888
    Abstract: An azo dye represented by the following general formulae (10) and (12): (wherein the variables are as defined herein) and a process for making the azo dye is disclosed. The process comprises a step in which a diazonium salt is formed by the reaction between an aminopyrazole represented by the general formula (3) and an diazotizing agent, a step in which a compound represented by the general formula (5) is formed by the reaction between the diazonium salt and an aromatic coupling agent represented by the general formula (4), and a step in which an azo dye represented by the general formula (6) is formed by the reaction between the compound represented by the general formula (5) and an arylating agent or a heterylating agent in the presence of a base.
    Type: Grant
    Filed: June 24, 2002
    Date of Patent: September 2, 2003
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Keiichi Tateishi, Toshiki Fujiwara, Makoto Yamada
  • Patent number: 6489452
    Abstract: An azo dye represented by the following general formula (1) and a process for making the azo dye is disclosed. The process comprises a step in which a diazonium salt is formed by the reaction between an aminopyrazole represented by the general formula (3) and an diazotizing agent, a step in which a compound represented by the general formula (5) is formed by the reaction between the diazonium salt and an aromatic coupling agent represented by the general formula (4), and a step in which an azo dye represented by the general formula (6) is formed by the reaction between the compound represented by the general formula (5) and an arylating agent or a heterylating agent in the presence of a base.
    Type: Grant
    Filed: March 21, 2001
    Date of Patent: December 3, 2002
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Keiichi Tateishi, Toshiki Fujiwara, Makoto Yamada
  • Patent number: 6235100
    Abstract: In one embodiment, the present invention relates to a method of preparing a medium shade yellow pigment composition comprising making an azo pigment by coupling (i) two or more diazonium components made from two or more aromatic amines including 2-amino-5-chloro-4-ethylbenzene-1-sulfonic acid and 2-amino-4-chloro-5-methylbenzene-1-sulfonic acid with (ii) at least 1-(3′-sulfophenyl)-3-methyl-5-pyrazolone, and metallizing the azo pigment with a divalent metal to provide the medium shade yellow pigment composition. The medium shade yellow pigment composition is suitable for use in plastics, paints and inks.
    Type: Grant
    Filed: June 24, 1999
    Date of Patent: May 22, 2001
    Assignee: Engelhard Corporation
    Inventor: Byron G. Hays
  • Patent number: 6042621
    Abstract: The application is concerned with a compound of the formula (I) ##STR1## and a process for making the same. The compound is useful as fiber-reactive dyestuff in dyeing or printing onto hydroxy- or nitrogen-containing substrates. A printing composition comprising this fiber-reactive dyestuff and a copper phthalocyanine allows to obtain dyeings with less catalytic fading.
    Type: Grant
    Filed: August 11, 1998
    Date of Patent: March 28, 2000
    Assignee: Clariant Finance (BV) Limited
    Inventors: Roland Wald, Paul Doswald
  • Patent number: 5919915
    Abstract: An azo pyrazolone compound of the formula: ##STR1## wherein Z represents a substituent selected from Cl, Br, F, NO.sub.2, SO.sub.2 R, CO.sub.2 R, NHSO.sub.2 R.sup.1 and NHCOR.sup.1 in which R and R.sup.1 are hydrocarbyl groups and the sulphonic acid group in ring A is in the 3- or 4-position relative to the pyrazolyl group, said compound being in the form of a salt, and its use as a pigment.
    Type: Grant
    Filed: July 17, 1997
    Date of Patent: July 6, 1999
    Assignee: Zeneca Limited
    Inventors: Alan Patrick Chorlton, James Mason
  • Patent number: 5746821
    Abstract: Disclosed are compositions comprising one or more compounds characterized by the formula: ##STR1## wherein Ar is an aromatic moiety having at least one substituent which is an acid group or salt thereof; X is a hydrocarbyl, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide or sulfonic acid amide group; each Y is independently a hydrocarbyl, halogen, hydrocarbyloxy, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide, imidazolone, sulfonic acid amide or nitro group; and a is 1, 2 or 3. Also disclosed is a process for preparing azo dyes which comprises coupling (i) at least one diazonium component of one or more aromatic amines containing at least one sulfonic acid group or carboxylic acid group, or salts thereof; with (ii) at least one coupling component represented by the formula: ##STR2## wherein X, Y and a are as defined above. The dye compositions prepared by this process and the azo pigments derived from such dyes are also disclosed.
    Type: Grant
    Filed: February 13, 1995
    Date of Patent: May 5, 1998
    Assignee: Engelhard Corporation
    Inventor: Byron G. Hays
  • Patent number: 5669967
    Abstract: Disclosed are compositions comprising one or more compounds characterized by the formula: ##STR1## wherein X is a hydrocarbyl, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide or sulfonic acid amide group; Y is a hydrocarbyl, halogen or hydrocarbyloxy group; Ar is an aromatic moiety characterized by the formula: ##STR2## wherein A is a halogen group; each Z is independently a --COOH or --SO.sub.3 H group, or salts of such groups; m is 1 or 2; each R is independently a halogen, hydrocarbyl, hydrocarbyloxy, carboxylic acid ester, sulfonic acid ester, carboxylic amide, imidazolone, sulfonic acid amide, nitro group; and n is 0, 1 or 2.A process for preparing azo dyes, the dye compositions prepared by this process and the azo pigments derived from such dyes are also disclosed. Paint, ink and plastic compositions containing the foregoing pigments compositions are disclosed.
    Type: Grant
    Filed: May 30, 1996
    Date of Patent: September 23, 1997
    Assignee: Engelhard Corporation
    Inventor: Byron G. Hays
  • Patent number: 5510468
    Abstract: There are described benzophenoneazo dyes of the formula ##STR1## where the ring A can be benzofused and a benzofused ring A can be overbridges,m is 1 or 2,K is the radical of a coupling component,Y is hydrogen or arylazo,one of the two radicals X.sup.1 and X.sup.2 is hydrogen and the other is hydroxysulfonyl,R.sup.1, R.sup.2 and R.sup.3 are independently of the others hydrogen, halogen, C.sub.1 -C.sub.12 -alkyl, cyclohexyl, phenyl, 2-hydroxy-ethylsulfonyl or C.sub.1 -C.sub.4 -alkoxy or, when m is 1 and Y is hydrogen, one of these substituents can also be the radical of the formula ##STR2## where L.sup.1 is a chemical bond or a bridge member, and X.sup.1, X.sup.2, R.sup.4, K and the ring A are each as defined above, andR.sup.4 is hydrogen, halogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: July 27, 1994
    Date of Patent: April 23, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Gunther Lamm, Helmut Reichelt, Ortwin Schaffer
  • Patent number: 5502174
    Abstract: Fibre-reactive dyestuffs based on barbituric acid, of the following formula ##STR1## wherein the substituents have the meaning given in the description, are distinguished by improved properties.
    Type: Grant
    Filed: August 25, 1994
    Date of Patent: March 26, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Stefan Ehrenberg, Aloysius Engel, Hermann Henk
  • Patent number: 5457188
    Abstract: An azo lake of the formula ##STR1## in which ##STR2## R.sup.1 =--OH or --NR.sup.4 R.sup.5, R.sup.2 = ##STR3## except the lake of the formula ##STR4## Such azo lakes are useful as pigments.
    Type: Grant
    Filed: July 22, 1994
    Date of Patent: October 10, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventor: Gesine Zimmermann
  • Patent number: 5380859
    Abstract: There are described benzophenoneazo dyes of the formula ##STR1## where the ring A can be benzofused and a benzofused ring A can be overbridged,m is 1 or 2,K is the radical of a coupling component,Y is hydrogen or arylazo,one of the two radicals X.sup.1 and X.sup.2 is hydrogen and the other is hydroxysulfonyl,R.sup.1, R.sup.2 and R.sup.3 are independently of the others hydrogen, halogen, C.sub.1 -C.sub.12 -alkyl, cyclohexyl, phenyl, 2-hydroxyethylsulfonyl or C.sub.1 -C.sub.4 -alkoxy or, when m is 1 and Y is hydrogen, one of these substituents can also be the radical of the formula ##STR2## where L.sup.1 is a chemical bond or a bridge member, andX.sup.1, X.sup.2, R.sup.4, K and the ring A are each as defined above, andR.sup.4 is hydrogen, halogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: July 16, 1993
    Date of Patent: January 10, 1995
    Assignee: Basf Aktiengesellschaft
    Inventors: Gunther Lamm, Helmut Beichelt, Ortwin Schaffer
  • Patent number: 5278291
    Abstract: A process for the preparation of the sulphone of the formula ##STR1## consists in reductive cleavage of azo/azoxy dyestuffs of the formula ##STR2## where D is a radical of a diazo component from the benzene or naphthalene series.The invention also relates to the azo/azoxy dyestuffs mentioned.
    Type: Grant
    Filed: October 9, 1992
    Date of Patent: January 11, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventor: Karl-Josef Herd
  • Patent number: 5151505
    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, --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.sup.4 and R.sup.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: November 13, 1990
    Date of Patent: September 29, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Stefan Hari, Georg Cseh
  • Patent number: 5106960
    Abstract: The present invention relates to azo dyes of the formula ##STR1## wherein X is an aryloxy radical or an unsubstituted or substituted C.sub.1 -C.sub.12 alkyl radical, a cycloalkyl radical or an aryl radical or a group of the formula ##STR2## wherein R.sub.1 is hydrogen, unsubstituted or substituted lower alkyl, cycloalkyl or aryl, and R.sub.2 is hydrogen or unsubstituted or substituted lower alkyl, or wherein R.sub.1 and R.sub.2, together with the nitrogen atom to which they are attached, form a 5- or 6-membered heterocyclic ring which may contain a further hetero-atom, Y is halogen, low molecular alkyl or low molecular alkoxy, and K is the radical of a coupling component of the benzene or naphthalene series or of the heterocyclic series.These dyes yield dyeings of good light- and wetfastness on polyamide material.
    Type: Grant
    Filed: March 22, 1991
    Date of Patent: April 21, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Rudolf Hurter, Dieter Mausezahl
  • 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: 5043269
    Abstract: A novel chromogenic substrate to peroxidase enzymes is provided which is comprised of a mixture of a colorless mixture of two compounds, such as, 3-methyl-2-benzothiazolinone hydrazone and 2-hydroxy-2,4,6-cycloheptatrienone, which undergo an oxidative coupling in the presence of peroxidase and hydrogen peroxide forming a purple indamine dye. Under certain circumstances the dye will precipitate out from the buffered solution and thus provide a permanent record of the determination. The mixture is also stable and unaffected by oxygen of the air or by hydrogen peroxide.
    Type: Grant
    Filed: February 16, 1988
    Date of Patent: August 27, 1991
    Inventor: Spyros Theodoropulos
  • 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: 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: 4880431
    Abstract: A monoazo compound of the following formula, ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are independently hydrogen or alkyl, R.sub.4 is alkyl or carboxy, A is ##STR2## in which R.sub.5 is hydrogen, methyl, methoxy, ethoxy, sulfo or carboxy, X is hydrogen or sulfo, n is 0 or 1, and the asterisked linkage bonds to the azo group, B.sub.1 and B.sub.2 are independently phenylene or naphthylene, W is hydrogen, carbamoyl, sulfoalkyl, cyano, sulfo, chloro or bromo, and Y.sub.1 and Y.sub.2 are independently --CH.dbd.CH.sub.2, --CH.sub.2 CH.sub.2 OSO.sub.3 H or the like, which is useful for dyeing hydroxy group- or carbonamide group-containing materials in a deep yellow color excellent in various fastness properties such as light fastness, perspiration-light fastness and chlorine fastness.
    Type: Grant
    Filed: December 8, 1987
    Date of Patent: November 14, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazufumi Yokogawa, Naoki Harada, Takashi Omura
  • Patent number: 4820808
    Abstract: Complexes of the formula ##STR1## and salts thereof each cation of which is independently a non-chromophoric cation,wherein B is --CO--CH.dbd.CH--CO--, --CO--(CH.sub.2).sub.a --CO--, ##STR2## and each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is independently hydrogen, halo, nitro, C.sub.1-4 alkyl, C.sub.1-4 alkyoxy, --NHCO--R.sub.6, --CO--R.sub.7 or --SO.sub.2 --R.sub.8,wherein R.sub.6 is C.sub.1-4 alkyl or phenyl,R.sub.7 is hydroxy; --OR.sub.9 ; C.sub.1-4 alkyl; phenyl; phenyl substituted by 1 or 2 substituents selected from halo, nitro, C.sub.1-4 alkyl and C.sub.1-4 alkoxy; cyclohexyl; cyclohexyl substituted by 1 to 3 C.sub.1-4 alkyl groups; or --NR.sub.10 R.sub.11, and,R.sub.8 is hydroxy; C.sub.1-4 alkyl; C.sub.1-4 alkyl monosubstituted by halo or sulfato; C.sub.2-4 alkenyl; phenyl; phenyl substituted by 1 or 2 substituents selected from halo, nitro, C.sub.1-4 alkyl and C.sub.1-4 alkoxy; cyclohexyl; cyclohexyl substituted by 1 to 3 C.sub.1-4 alkyl groups; or --NR.sub.10 R.sub.
    Type: Grant
    Filed: November 5, 1986
    Date of Patent: April 11, 1989
    Assignee: Sandoz Ltd.
    Inventors: Kurt Brenneisen, Friedrich Lehr
  • Patent number: 4773937
    Abstract: The invention relates to pasty pigment formulations of pigments of the arylpararosanilinesulfonic acid series, which are free of aromatics-containing mineral oils and are suitable for preparing printing inks, in particular letterpress and offset printing inks. The pigment formulations are obtainable by flushing aqueous presscakes of the pigments by means of the solution of a flushing resin in aromatics-free mineral oil and preparing the flushed paste obtained with an oil- or fatty-acid modified alkyd resin.
    Type: Grant
    Filed: December 5, 1986
    Date of Patent: September 27, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Manfred Schneider, Christa Uhde, Manfred Zimmermann
  • Patent number: 4652633
    Abstract: Compounds useful for dyeing nylon, wool, and leather, having the formula: ##STR1## wherein X.sup.1 is chlorine, bromine, methyl or trifluoromethyl, Y.sup.3 is chlorine or bromine, and K.sup.1 is a radical of the formula ##STR2## where R.sup.3 is C.sub.2 to C.sub.4 hydroxyalkyl, methoxyethyl or methoxypropyl.
    Type: Grant
    Filed: February 15, 1985
    Date of Patent: March 24, 1987
    Assignee: BASF Aktiengesellschaft
    Inventor: Gunther Lamm
  • Patent number: 4594411
    Abstract: This invention relates to a method of dyeing thermoplastics with sulfonated monoazo colorant lakes having a sulfophenyl pyrazole substituent, of general formula ##STR1## wherein R is CH.sub.3 or COO.sup.- ; X is Cl, CH.sub.3, CH.sub.3 O, C.sub.2 H.sub.5 O, C.sub.2 H.sub.5 CONH, NH.sub.2 CONH, C.sub.6 H.sub.5 CONH, CH.sub.3 SO.sub.2 NH, C.sub.6 H.sub.5 SO.sub.2 NH, CH.sub.3 CONH, or hydrogen; Y is hydrogen, Cl, or CH.sub.3 ; Z is hydrogen or Cl, n is 0, 1 or 2; and Me.sup.+ is one equivalent of a cation selected from the group consisting of NH.sub.4.sup.+, Li.sup.+, K.sup.+, Na.sup.+, 1/2Sr.sup.2+, 1/2Mn.sup.2+, 1/2Ni.sup.2+, 1/2Ba.sup.2+, 1/2Mg.sup.2+ and 1/2Ca.sup.2+ ; with the proviso that if R is COO.sup.-, the additional equivalent charge is compensated by a further equivalent of said or another cation.
    Type: Grant
    Filed: June 6, 1984
    Date of Patent: June 10, 1986
    Assignee: BASF Aktiengesellschaft
    Inventor: Georg Henning
  • 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: 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: 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: 4486347
    Abstract: The halogenated azo dyestuffs of the present invention possess fire-proofing and antimicrobial properties and have the following general formula: ##STR1##
    Type: Grant
    Filed: January 22, 1982
    Date of Patent: December 4, 1984
    Assignee: Tsentralny Nauchnoissledovatelsky Institut Shersti
    Inventors: Irina N. Gorbacheva, Ljudmila M. Sukhova, Zinaida J. Kozinda, Vladislav L. Molokov, Lev T. Antonov, Vadim D. Simonov, Viktor A. Chertov, Semen I. Dvoskin, Raisa S. Veseneva
  • Patent number: RE35359
    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, --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.sup.4 and R.sup.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.6 -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: September 26, 1994
    Date of Patent: October 22, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Stefan Hari, Georg Cseh