Heterocyclic Amine Dye Patents (Class 8/409)
  • Patent number: 6077320
    Abstract: Diiminoisoindoline derivatives or 3-aminoisoindolone derivatives, or tautomeric forms thereof, used as oxidizing-agent-free dye precursors in dyeing keratin fibers, in particular human keratin fibers such as the hair, without an oxidizing agent, in the presence of compounds containing a primary or secondary amine function; dye compositions containing these compounds and to the dyeing devices and processes used.
    Type: Grant
    Filed: December 11, 1997
    Date of Patent: June 20, 2000
    Assignee: L'Oreal
    Inventors: Herve Andrean, Alain Lagrange
  • Patent number: 6074438
    Abstract: The invention provides compositions and methods for the oxidative coloring of human hair. The compositions of the invention contain as a primary intermediate at least one aminophenol of the formulas: ##STR1## or a cosmetically acceptable salt thereof, and at least one pyrazolone coupler of the formulas: ##STR2## or a cosmetically acceptable salt thereof. The compositions may also contain one or more other primary intermediates and conventional coupling compounds, in addition to an oxidizing agent and other components typically used in oxidative hair dye preparations.
    Type: Grant
    Filed: March 3, 1998
    Date of Patent: June 13, 2000
    Assignee: Bristol-Myers Squibb Co.
    Inventors: Mu-Ill Lim, Yuh-Guo Pan, Linas R. Stasaitis
  • Patent number: 6074439
    Abstract: An oxidation dye composition for keratin fibers, in particular for human keratin fibers such as the hair, this composition comprising, in a medium which is suitable for dyeing, at least one oxidation dye precursor and optionally one or more couplers, and also an anionic amphiphilic polymer containing at least one hydrophilic unit, and at least one allyl ether unit containing a fatty chain, and dyeing processes and dyeing devices using the oxidation composition.
    Type: Grant
    Filed: April 16, 1999
    Date of Patent: June 13, 2000
    Assignee: L'Oreal
    Inventors: Roland De La Mettrie, Fran.cedilla.oise Boudy
  • Patent number: 6063136
    Abstract: The present invention relates to a composition and a dyeing process for the dyeing of keratinous fibers, in particular of human hair, having,as coupler, at least one compound of formula: ##STR1## where Z.sub.a and Z.sub.b, which are different from one another, represent an oxygen or nitrogen atom,and at least one oxidation base.
    Type: Grant
    Filed: February 26, 1999
    Date of Patent: May 16, 2000
    Assignee: L'Oreal S.A.
    Inventors: Laurent Vidal, Gerard Malle
  • Patent number: 6042620
    Abstract: New p-diaminobenzene derivative compounds of the formula (I): ##STR1## and physiologically compatible water soluble salts thereof are described, wherein X represents oxygen, sulfur, selenium or N-R9, wherein R9 represents hydrogen, an alkyl group, a hydroxyalkyl group, a phenyl group or an acetyl group; and the remaining R groups each represent variously hydrogen, hydroxy, amino, nitro, nitrile, alkyl, alkoxy, hydroxyalkyl, cyclic or aromatic groups, among others. Compositions for dyeing keratin fibers including a combination of coupler and developer substance are disclosed, in which the developer substance includes at least one of the new p-diaminobenzene derivative compounds.
    Type: Grant
    Filed: February 25, 1999
    Date of Patent: March 28, 2000
    Assignee: Wella AG
    Inventors: Hans-Juergen Braun, Laurent Chassot
  • Patent number: 6027538
    Abstract: A composition for the oxidation dyeing of keratinous fibers containing at least one coupler selected from indazoleamine derivatives and acid addition salts thereof and at least one oxidation base. Another aspect of the invention is the use of indazoleamine derivatives as coupler for the oxidation dyeing of keratinous fibers, in combination with at least one oxidation base, and the dyeing processes employing them.
    Type: Grant
    Filed: August 24, 1998
    Date of Patent: February 22, 2000
    Assignee: L'Oreal S.A.
    Inventors: Jean Jacques Vandenbossche, Alain Lagrange
  • Patent number: 6004356
    Abstract: A composition for the oxidation dyeing of keratin fibers, in particular human keratin fibers such as the hair, comprising at least one suitably selected oxidation base, at least one meta-aminophenol as first coupler and 4-hydroxyindoline and/or at least one of the addition salts thereof with an acid as second coupler, and dyeing processes using this composition with an oxidizing agent.
    Type: Grant
    Filed: December 30, 1997
    Date of Patent: December 21, 1999
    Assignee: L'Oreal
    Inventor: Marie-Pascale Audousset
  • Patent number: 6002018
    Abstract: The invention relates to N-substituted 4-hydroxyindoline derivatives, to their process of synthesis, to their use as couplers for the oxidation of dyeing of keratinous fibers, in combination with at least one oxidation base, and to the dyeing processes in which they are used.
    Type: Grant
    Filed: January 28, 1998
    Date of Patent: December 14, 1999
    Assignee: L'Oreal
    Inventors: Eric Terranova, Aziz Fadli, Alain Lagrange
  • Patent number: 6001134
    Abstract: Oxidation dyeing compositions for keratinous fibers which contain an oxidation enzyme derived from a strain of the genus Pyricularia, one or more dye precursors, and optionally, one or more modifiers, and methods for dyeing hair with such compositions.
    Type: Grant
    Filed: September 22, 1998
    Date of Patent: December 14, 1999
    Assignee: Novo Nordisk A/S
    Inventor: Niels Henrik S.o slashed.rensen
  • Patent number: 6001135
    Abstract: A ready-to-use composition for the oxidation dyeing of keratin fibers, in particular human keratin fibers such as the hair, this ready-to-use composition comprising at least one oxidation base in combination with at least one selected cationic direct dye and at least one oxidizing agent, as well as to the dyeing process using this ready-to-use composition.
    Type: Grant
    Filed: December 19, 1997
    Date of Patent: December 14, 1999
    Assignee: L'Oreal
    Inventors: Christine Rondeau, Jean Cotteret, Roland De La Mettrie
  • Patent number: 5993490
    Abstract: A ready-to-use composition for the oxidation dyeing of keratin fibers, in particular human keratin fibers such as the hair, comprising at least one oxidation base selected from para-phenylenediamines and bis(phenyl)alkylenediamines, in combination with at least one coupler selected from meta-diphenols, at least one selected cationic direct dye and at least one oxidizing agent, as well as to the dyeing process using this composition.
    Type: Grant
    Filed: December 19, 1997
    Date of Patent: November 30, 1999
    Assignee: L'Oreal
    Inventors: Christine Rondeau, Jean Cotteret, Roland de la Mettrie
  • Patent number: 5993491
    Abstract: Compositions and methods for the oxidative coloring of human hair, wherein the compositions contain as a novel primary dye intermediate a 1-(4-aminophenyl)-2-pyrrolidinemethanol, or a cosmetically acceptable salt thereof. The compositions may also contain at least one other primary intermediate and conventional coupling compounds, in addition to an oxidizing agent and other components typically used in oxidative hair dye preparations. A preferred dye intermediate in the composition is 1-(4-aminophenyl)-2-pyrrolidinemethanol or cosmetically acceptable salts thereof, which produce intense black colors when used in admixture with a suitable coupling agents, such as 3-aminophenol, in conventional hair dye base formulations.
    Type: Grant
    Filed: May 13, 1998
    Date of Patent: November 30, 1999
    Assignee: Bristol-Myers Squibb Company
    Inventors: Mu-Ill Lim, Margaret Popp, Yuh-Guo Pan
  • Patent number: 5989295
    Abstract: An oxidation dye composition for keratin fibers, in particular for human keratin fibers such as the hair, comprising, in a medium which is suitable for dyeing, at least one oxidation dye precursor and optionally one or more couplers, which is characterized in that it also contains an anionic amphiphilic polymer containing at least one hydrophilic unit of an unsaturated olefinic carboxylic acid, and at least one hydrophobic unit which is a (C.sub.10 -C.sub.30)alkyl ester of unsaturated carboxylic acid, preferably exclusively of said (C.sub.10 -C.sub.30)alkyl ester of unsaturated carboxylic acid. The oxidation dye compositions are used in dyeing processes and dyeing devices.
    Type: Grant
    Filed: September 5, 1997
    Date of Patent: November 23, 1999
    Assignee: L'Oreal
    Inventors: Roland de la Mettrie, Fran.cedilla.oise Boudy
  • Patent number: 5980585
    Abstract: A composition for the oxidation dyeing of keratinous fibers comprising at least one imidazopyridine derivative as coupler and at least one oxidation base and the use of such an imidazopyridine derivative as a coupler, in combination with at least one oxidation base, for the oxidation dyeing of keratinous fibers and the dyeing processes employing them.
    Type: Grant
    Filed: December 16, 1998
    Date of Patent: November 9, 1999
    Assignee: L'Oreal
    Inventors: Eric Terranova, Aziz Fadli, Alain Lagrange
  • Patent number: 5976195
    Abstract: An oxidation dye composition for keratin fibers, in particular for human keratin fibers such as the hair, comprising, in a medium which is suitable for dyeing, at least one oxidation dye precursor and optionally one or more couplers, and also an anionic amphiphilic polymer containing at least one hydrophilic unit, and at least one allyl ether unit containing a fatty chain. The oxidation dye compositions are used in dyeing processes and dyeing kits.
    Type: Grant
    Filed: May 20, 1997
    Date of Patent: November 2, 1999
    Assignee: L'Oreal
    Inventors: Roland de la Mettrie, Fran.cedilla.oise Boudy
  • Patent number: 5968206
    Abstract: A ready-to-use composition for the oxidation dyeing of keratinous fibers, especially of human keratinous fibers such as hair, which comprises, in an alkaline medium (pH>7), an appropriately selected para-phenylenediamine derivative in combination with 4-hydroxyindole and an oxidizing agent, and dyeing processes using this composition.
    Type: Grant
    Filed: June 30, 1998
    Date of Patent: October 19, 1999
    Assignee: L'Oreal
    Inventors: Marie-Pascale Audousset, Jean Cotteret
  • Patent number: 5961667
    Abstract: A new oxidizing agent composition for mixing with oxidation dye pre-cursor compounds, such as developer and coupler substances, to form a ready-to-use dye mixture for dyeing keratin fibers is described. The oxidizing agent composition contains from 0.01 to 25 percent by weight of at least one alkaline earth peroxide, based on the ready-to-use dye mixture, and from 0.01 to 25 percent by weight of at least one inorganic or organic acid, salt of the at least one organic or inorganic acid or mixture of the salt and/or the at least one acid, based on the ready-to-use dye mixture.
    Type: Grant
    Filed: January 30, 1998
    Date of Patent: October 5, 1999
    Assignee: Wella AG
    Inventors: Annelie Doehling, Dirk Lauscher
  • Patent number: 5961668
    Abstract: Compounds of the formula (I): ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently of one another may represent a hydrogen atom, a (C.sub.1-4) alkyl group, a hydroxy (C.sub.2-3) alkyl group, an alkoxy (C.sub.2-3) alkyl group, an amino (C.sub.2-3) alkyl group or a 2,3-dihydroxypropyl group and R.sub.5 and R.sub.6 independently of one another may represent hydrogen or a (C.sub.1-4) alkyl group, are made by reacting 2,4-dinitrohalobenzenes with 4-hydroxymethyl-1,3-dioxolanes under alkaline conditions to form 4-(2,4-dinitrophenoxymethyl)-1,3-dioxolanes, which are further reduced to the compounds of formula (I). In an alternate process, the 4-hydroxymethyl-1,3-dioxolanes are reacted with 4-halo-3-nitranilines or 2-halo-5-nitranilines, the product further reacted first under basic conditions with chloroformic acid ester followed by treatment with strong base, alkylation or alkoxylation, reduction, and optionally further alkylation of alkoxylation to arrive at the compounds (I).
    Type: Grant
    Filed: May 13, 1998
    Date of Patent: October 5, 1999
    Assignee: Hans Schwarzkopf GmbH & Co. KG
    Inventors: Mustafa Akram, Wolfgang Bauer, Andreas Bittner, Astrid Kleen
  • Patent number: 5938792
    Abstract: The invention relates to a process for dyeing keratinous fibres, which consists in applying to these fibres a composition containing, in a suitable medium for dyeing, at least one coupler of formula: ##STR1## where R.sub.1 denotes hydrogen or alkyl,R.sub.2 and R.sub.3 denote hydrogen, alkyl, COOR' where R' is alkyl or hydrogen,at least one of the groups R.sub.2 and R.sub.3 denoting hydrogen,R.sub.4 denotes hydrogen, alkyl, hydroxyalkyl, polyhydroxyalkyl or aminoalkyl,Z.sub.1 and Z.sub.2 denote hydrogen, alkyl, hydroxyl, halogen, alkoxy,at least one of the groups Z.sub.1 and Z.sub.2 is other than hydrogenat least one oxidation dye precursor,at least one oxidizing agent, the pH of the composition applied to the fibres being higher than 7.
    Type: Grant
    Filed: July 8, 1997
    Date of Patent: August 17, 1999
    Assignee: L'Oreal
    Inventors: Gerard Lang, Alex Junino, Jean Cotteret, Alain Lagrange
  • Patent number: 5922086
    Abstract: A method of preparing an oxidation dyestuff comprising the step of:mixing a coupler substance of formula I ##STR1## wherein R.sup.1 is hydrogen, (C.sub.1 -C.sub.6)-alkyl, hydroxy-(C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.4)-alkoxy-(C.sub.1 -C.sub.6)-alkyl, carboxy-(C.sub.1 -C.sub.6)-alkyl, 2,3-dihydroxypropyl, 2-hydroxy-3-((C.sub.1 -C.sub.4)-alkoxy)-propyl, cyano-(C.sub.1 -C.sub.6)-alkyl, carbamoyl-(C.sub.1 -C.sub.6)-alkyl, ((C.sub.1 -C.sub.4)-alkoxy) carbonyl-(C.sub.1 -C.sub.4)-alkyl, benzyl, phenyl or substituted phenyl;R.sup.2 is hydrogen, (C.sub.1 -C.sub.6)-alkyl, hydroxy-(C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.4)-alkoxy-(C.sub.1 -C.sub.6)-alkyl, oxo-(C.sub.1 -C.sub.6)-alkyl, carboxy-(C.sub.1 -C.sub.6)-alkyl, ((C.sub.1 -C.sub.4)-alkoxy) carbonyl-(C.sub.1 -C.sub.6)-alkyl, carbamoyl-(C.sub.1 -C.sub.6)-alkyl, carboxyl, ((C.sub.1 -C.sub.4)-alkoxy) carbonyl, carbamoyl, phenyl, substituted phenyl or pyridyl;R.sup.3 is (C.sub.1 -C.sub.
    Type: Grant
    Filed: March 27, 1998
    Date of Patent: July 13, 1999
    Assignee: Clariant GmbH
    Inventors: Wolfgang Bauer, Mustafa Akram, Herbert Deutz
  • Patent number: 5919273
    Abstract: A ready-to-use composition for the oxidation dyeing of keratin fibers, in particular human keratin fibers such as hair, comprising at least one oxidation base in combination with at least one coupler of substituted meta-aminophenol type, at least one cationic direct dye and at least one oxidizing agent, as well as to the dyeing process using this composition.
    Type: Grant
    Filed: December 19, 1997
    Date of Patent: July 6, 1999
    Assignee: L'Oreal
    Inventors: Christine Rondeau, Jean Cotteret, Roland de la Mettrie
  • Patent number: 5900028
    Abstract: An oxidation dye composition for keratin fibre, in particular human hair, comprising at least one 2-amino-3-hydroxypyridine as coupler, in combination with at least one suitably selected oxidation base, as well as the dyeing process using this composition with an oxidizing agent.
    Type: Grant
    Filed: October 4, 1996
    Date of Patent: May 4, 1999
    Assignee: L 'Oreal
    Inventor: Marie-Pascale Audousset
  • Patent number: 5879412
    Abstract: A ready-to-use composition for the oxidation dyeing of keratin fibers, in particular human keratin fibers such as hair, this composition comprising at least one oxidation base selected from para-phenylenediamines and bis(phenyl)-alkylenediamines, in combination with at least one coupler selected from meta-phenylenediamines, at least one selected cationic direct dye and at least one oxidizing agent, as well as to the dyeing process using this composition.
    Type: Grant
    Filed: December 19, 1997
    Date of Patent: March 9, 1999
    Assignee: L'Oreal
    Inventors: Christine Rondeau, Jean Cotteret, Roland de la Mettrie
  • Patent number: 5876464
    Abstract: N-(4-Aminophenol) prolineamide and cosmetically acceptable salts thereof are useful as primary intermediates in oxidative hair dyeing. Compositions which contain a hair dye produced by oxidatively coupling N-(4-aminophenol) prolineamide with a coupler in the presence of an oxidizing agent are applied to the hair in oxidative hair dyeing processes.
    Type: Grant
    Filed: February 17, 1998
    Date of Patent: March 2, 1999
    Assignee: Bristol-Myers Squibb Company
    Inventors: Mu-Ill Lim, Margaret A. Popp, Yuh-Guo Pan
  • Patent number: 5876465
    Abstract: A composition for dyeing keratin fibres, and in particular human keratin fibres such as the hair, characterized in that it comprises, in a medium which is suitable for dyeing:at least one coupler selected from 2-iminoindoline derivatives of formula (I) and acid addition salts thereof: ##STR1## in which: R.sub.1 represents hydrogen, alkyl, hydroxyalkyl, alkoxycarbonyl or acyl;R.sub.2 represents hydrogen, alkyl, phenyl or arylsulphonyl;R.sub.3 represents hydrogen or alkyl which may be substituted with one or more hydroxyl, alkoxy, amino, alkylamino, dialkylamino, cyano or aryl groups;R.sub.4 and R.sub.5, which may be identical or different, denote hydrogen, hydroxyl, alkyl, alkoxy, amino, alkylamino, dialkylamino, aralkyl, halogen or a nitro group; andat least one oxidation base.
    Type: Grant
    Filed: August 22, 1997
    Date of Patent: March 2, 1999
    Assignee: L'Oreal
    Inventors: Eric Terranova, Aziz Fadli, Alain Lagrange
  • Patent number: 5873910
    Abstract: A process for the two-stage oxidation dyeing of keratin fibers by applying to the keratin fibers:in a first stage, at least one composition A containing at least one manganese salt and/or a manganese complex,in a second stage, at least one composition B having a pH of greater than or equal to 6, and resulting from the extemporaneous mixing of at least one composition B1 containing at least one 4-substituted 1-naphthol and at least one composition B2 containing at least one oxidizing agent, and corresponding multi-compartment dyeing kit.
    Type: Grant
    Filed: December 19, 1997
    Date of Patent: February 23, 1999
    Assignee: L'Oreal
    Inventors: Jean-Christophe Henrion, Herve Andrean
  • Patent number: 5868800
    Abstract: The invention relates to an oxidation dyeing composition for keratinous fibres, in particular for human keratinous fibres such as hair, of the type which comprises, in a medium appropriate for dyeing, at least one oxidation dye precursor and at least one coupler, and which is characterized in that it contains, as oxidation dye precursor, at least one para-phenylenediamine which is substituted in position 2 on the benzene ring, and/or at least one of its addition salts with an acid, and, as coupler, at least one specific 6-hydroxy-1,4-benzomorpholine and/or at least one of its addition salts with an acid. The invention also relates to the use of this composition for the dyeing of keratinous fibres, especially hair.
    Type: Grant
    Filed: June 10, 1997
    Date of Patent: February 9, 1999
    Assignee: L'Oreal
    Inventors: Jean Cotteret, Marie-Pascale Audousset
  • Patent number: 5865855
    Abstract: The new bis-pyrazole aza compounds have the formula (I): ##STR1## wherein R.sub.1, R.sub.1 ', R.sub.2, R.sub.2 ', R.sub.3 and R.sub.3 ' are the same or different, and are each, independently of each other, H, a straight, branched or cyclic alkyl group having 1 to 6 carbon atoms, a straight chain or branched monohydroxyalkyl group or polyhydroxyalkyl group with 1 to 6 carbon atoms, a straight or branched alkoxyalkyl group with 2 to 6 carbon atoms, a straight or branched monoaminoalkyl group or polyaminoalkyl group with 2 to 6 carbon atoms, or an unsubstituted aromatic or heteroaromatic ring, or a substituted aromatic or heteroaromatic ring having one or more halogen, a C.sub.1 - to C.sub.4 -alkyl group, a nitro group, a sulfonic acid group, a carboxylic acid group or a C.sub.1 - to C.sub.4 -alkoxy substituent, or an unsubstituted benzyl group, or a benzyl group substituted with one or more halogen atom, a hydroxy group, a C.sub.1 - to C.sub.4 - alkyl group, a nitro group or a C.sub.1 - to C.sub.
    Type: Grant
    Filed: June 24, 1998
    Date of Patent: February 2, 1999
    Assignee: Wella Aktiengesellschaft
    Inventors: Annelie Doehling, Wolfram Geibel, Otto Goettel
  • Patent number: 5851237
    Abstract: The invention provides compositions and methods for the oxidative coloring of human hair. The compositions of the invention contain as a primary dye intermediate a 1-(4-aminophenyl) pyrrolidine, or a cosmetically acceptable salt thereof. The compositions may also contain at least one other primary intermediate and conventional coupling compounds, in addition to an oxidizing agent and other components typically used in oxidative hair dye preparations. Preferred dye intermediates in the compositions of the invention include 1-(4-aminophenyl) pyrrolidine and 1-(4-amino-3-methylphenyl) pyrrolidine, or cosmetically acceptable salts thereof, which produce intense neutral colors when used in admixture with a suitable coupling agents, such as 3-aminophenol, in conventional hair dye base formulations.
    Type: Grant
    Filed: July 14, 1997
    Date of Patent: December 22, 1998
    Inventors: James S. Anderson, Michael Y. M. Wong
  • Patent number: 5814106
    Abstract: The present invention relates to a ready-to-use composition for the oxidation dyeing of keratin fibers, in particular human keratin fibers such as the hair, this composition comprising, in an acidic medium (pH<7), at least one oxidation base, in combination with 4-hydroxyindoline as coupler, and an oxidizing agent, as well as to the dyeing process using this composition.
    Type: Grant
    Filed: May 22, 1997
    Date of Patent: September 29, 1998
    Assignee: L'Oreal
    Inventor: Marie-Pascale Audousset
  • Patent number: 5792220
    Abstract: The present invention concerns improved processes for dyeing keratinous fibers especially hair on the human scalp using a two-step oxidation process for the oxidation of the melanin precursors 5,6-dihydroxyindoline (DHIN), 5,6-dihydroxyindole (DHI), and derivatives thereof such as 5,6-dihydroxyindole-2-carboxylic acid (DHICA).
    Type: Grant
    Filed: May 16, 1997
    Date of Patent: August 11, 1998
    Assignee: Bristol-Myers Squibb Company
    Inventors: Gottfried Wenke, Giuseppe Prota
  • Patent number: 5785717
    Abstract: The present invention relates to a composition for the oxidation dyeing of keratin fibers, in particular human keratin fibers such as the hair, comprising at least one diaminopyrazole derivative as oxidation base in combination with at least one suitably selected heterocyclic coupler, and to the dyeing process using this composition with an oxidizing agent.
    Type: Grant
    Filed: February 27, 1996
    Date of Patent: July 28, 1998
    Assignee: L'Oreal
    Inventors: Mireille Maubru, Marie-Pascale Audousset
  • Patent number: 5769902
    Abstract: Compositions for dyeing keratinous fibers comprising at least one an ortho-diaminopyrazole or an acid addition salt thereof and a manganese salt as well as a dyeing process using these compositions, without any oxidizing agent other than atmospheric oxygen.
    Type: Grant
    Filed: June 19, 1996
    Date of Patent: June 23, 1998
    Assignee: L'Oreal
    Inventor: Henri Samain
  • Patent number: 5769903
    Abstract: The present invention relates to a composition for the oxidation dyeing of keratin fibers, in particular human keratin fibers such as the hair, comprising an oxidation base in combination with at least one suitably selected indole coupler and at least one additional heterocyclic coupler which is also suitably selected, as well as to the dyeing process using this composition with an oxidizing agent.
    Type: Grant
    Filed: April 17, 1997
    Date of Patent: June 23, 1998
    Assignee: L'Oreal
    Inventors: Marie-Pascale Audousset, Jean Cotteret
  • Patent number: 5755829
    Abstract: The subject of the invention is a composition for the oxidation dyeing of keratinous fibers containing at least one N-substituted 4-hydroxyindoline derivative as coupler and at least one oxidation base. The invention also relates to new N-substituted 4-hydroxyindoline derivatives, to their process of synthesis, to their use as couplers for the oxidation dyeing of keratinous fibers, in combination with at least one oxidation base, and to the dyeing processes in which they are used.
    Type: Grant
    Filed: December 5, 1996
    Date of Patent: May 26, 1998
    Assignee: L'Oreal
    Inventors: Eric Terranova, Aziz Fadli, Alain Lagrange
  • Patent number: 5752982
    Abstract: A method for dyeing keratin fibers, wherein a composition is applied to said fibers which contains, in a suitable dyeing medium, at least one coupler having formula (I) ##STR1## wherein R.sub.1 is hydrogen or alkyl; R.sub.2 and R.sub.3 are hydrogen, alkyl, COOR', where R' is alkyl or hydrogen; R.sub.4 is hydrogen, hydroxyalkyl, alkyl, polyhydroxyalkyl or acetyl or aminoalkyl wherein the amine may be mono- or disubstituted by alkyl; Z.sub.1 and Z.sub.2 are hydrogen, alkyl, hydroxy, halogen, alkoxy or a salt thereof; at least one precursor of an oxidation hair dye; and at least one oxidizing agent, the pH of the composition applied to the fibers being less than 7.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: May 19, 1998
    Assignee: L'Oreal
    Inventors: Gerard Lang, Alex Junino, Jean Cotteret, Alain Lagrange
  • Patent number: 5752984
    Abstract: An oxidative coloring composition for coloring human hair cointaining an oxidation dye precursor in a water-containing carrier, wherein the dye precursor comprises 1,2,3,4-tetrahydroquinoxalines corresponding to formula (I): ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 independently of one another represent hydrogen, C.sub.1-4 alkyl groups, benzyl groups, 2-phenylethyl groups or C.sub.2-4 hydroxyalkyl groups and X, Y and Z represent hydrogen, fluorine, chlorine, bromine or iodine atoms or C.sub.1-4 alkyl groups, and wherein at least one of the groups X, Y and Z is hydrogen.
    Type: Grant
    Filed: August 12, 1996
    Date of Patent: May 19, 1998
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Georg Knuebel, David Rose, Horst Hoeffkes, Bernd Meinigke
  • Patent number: 5752983
    Abstract: The invention relates to a ready-for-use composition for the oxidation dyeing of keratinous fibres, in particular human keratinous fibres such as hair, including an oxidation dye precursor in combination with 4-hydroxyindole, a benzene-based coupler and an oxidizing agent in an alkaline medium, and to the dyeing process making use of this composition.
    Type: Grant
    Filed: January 22, 1996
    Date of Patent: May 19, 1998
    Assignee: L'Oreal
    Inventors: Marie-Pascale Audousset, Jean Cotteret
  • Patent number: 5746779
    Abstract: Quaternized blue anthraquinone compounds of Formula I ##STR1## wherein R.sub.1 and R.sub.2 are methyl and R.sub.3 is propyl, or R.sub.1 and R.sub.2 are ethyl and R.sub.3 is methyl and A.sup.- is a cosmetically acceptable anion, when employed in an isatin/amine dye system for the dyeing of hair enable the hair colorist to develop a full range of shades for the isatin/amine dye system. The compound of Formula I wherein R1 and R2 are methyl and R3 is propyl is preferred. Compositions and a method of use employing same are disclosed.
    Type: Grant
    Filed: July 12, 1996
    Date of Patent: May 5, 1998
    Assignee: Bristol-Myers Squibb Company
    Inventor: Keith Brown
  • Patent number: 5743919
    Abstract: The process of coloring keratin-containing fibers by contacting the fibers with an isatin derivative corresponding to formula (I): ##STR1## in which R.sup.1 is a hydroxy group, an optionally C.sub.1-4 -alkyl- or phenyl-substituted amino group, a C.sub.3-8 alkenyl, dihydroxy-(C.sub.3-6)-alkyl, trihydroxy-(C.sub.4-6)-alkyl, tetrahydroxy-(C.sub.5-6)-alkyl, pentahydroxy-C.sub.6 -alkyl, C.sub.2-4 -aminoalkyl, C.sub.1-4 -sulfoalkyl group, an optionally C.sub.1-4 -alkyl-substituted 2-furylmethyl, 2-thienylmethyl, 2-pyridylmethyl, 3-pyridylmethyl, 4-pyridylmethyl group or an aralkyl group corresponding to formula (II): ##STR2## in which R.sup.6 and R.sup.7 independently of one another represent hydrogen, halogen atoms, hydroxy groups, amino groups optionally substituted by C.sub.1-4 alkyl or phenyl, C.sub.1-4 alkyl groups, C.sub.1-4 alkoxy groups, carboxy groups or sulfo groups and R.sup.8 is hydrogen, a C.sub.1-4 alkyl group or a C.sub.2-4 hydroxyalkyl group and x=0, 1 or 2, and R.sup.2, R.sup.3, R.sup.4 and R.sup.
    Type: Grant
    Filed: September 17, 1996
    Date of Patent: April 28, 1998
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Hinrich Moeller, Horst Hoeffkes
  • Patent number: 5735909
    Abstract: A composition for the oxidation dyeing of keratin fibres, in particular human keratin fibres such as the hair, comprising at least one suitably selected oxidation base, at least one meta-aminophenol or an acid addition salt thereof as a first coupler, and at least one 6-hydroxyindoline or an acid addition salt thereof as a second coupler, and to the dyeing process using this composition with an oxidizing agent.
    Type: Grant
    Filed: February 27, 1996
    Date of Patent: April 7, 1998
    Assignee: L'Oreal
    Inventor: Mireille Maubru
  • Patent number: 5718731
    Abstract: The oxidation hair dye composition contains from 0.01 to 4.0 percent by weight of a developer substance including at least one diaminopyrazole of the formula (I) ##STR1## wherein R.sup.1 is selected from the group consisting of hydrogen, an alkyl group having from 1 to 6 carbon atoms, a hydroxyalkyl group having from 2 to 4 carbon atoms and a substituted or unsubstituted benzyl group, and R.sup.2 and R.sup.3, independently, are each selected from the group consisting of hydrogen, an alkyl group having from 1 to 6 carbon atoms and a hydroxyalkyl group having from 2 to 4 carbon atoms; and from 0.01 to 4.0 percent by weight of a coupler substance including at least one m-phenylenediamine selected from the group consisting of N-(3-dimethylamino)phenyl urea and 3-(N-methylsulfonyl)amino-N,N-dimethylaniline.
    Type: Grant
    Filed: August 13, 1996
    Date of Patent: February 17, 1998
    Assignee: Wella Aktiengesellschaft
    Inventors: Isolde Loewe, Alexa Weinges, Wolfgang R. Balzer, Stefan Gerstung
  • Patent number: 5704948
    Abstract: A composition for the oxidation dyeing of keratinous fibers containing at least one coupler selected from N-substituted 4-hydroxyindole compounds and acid addition salt thereofs and at least one oxidation base, N-substituted 4-hydroxyindole compounds, a process for synthesizing these substituted compounds, their use as couplers for the oxidation dyeing of keratinous fibers in combination with at least one oxidation base, as well as dyeing processes employing them.
    Type: Grant
    Filed: July 12, 1996
    Date of Patent: January 6, 1998
    Assignee: L'Oreal
    Inventors: Eric Terranova, Aziz Fadli, Alain Lagrange
  • Patent number: 5690695
    Abstract: The invention relates to an oxidation dyeing composition for keratinous fibres, in particular for human keratinous fibres such as hair, of the type which comprises, in a medium appropriate for dyeing, at least one oxidation dye precursor and at least one coupler, and which is characterized in that it contains, as oxidation dye precursor, at least one para-phenylenediamine which is substituted in position 2 on the benzene ring, and/or at least one of its addition salts with an acid, and, as coupler, at least one specific 6-hydroxy-1,4-benzomorpholine and/or at least one of its addition salts with an acid. The invention also relates to the use of this composition for the dyeing of keratinous fibres, especially hair.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: November 25, 1997
    Assignee: L'Oreal
    Inventors: Jean Cotteret, Marie-Pascale Audousset
  • Patent number: 5683474
    Abstract: Method for dyeing keratinous fibres, in particular human keratinous fibres such as hair, characterized in that a composition containing, in a medium appropriate for dyeing, at least one 4-hydroxyindole derivative of formula: ##STR1## in which R.sub.1 denotes hydrogen or C.sub.1 -C.sub.4 alkyl; R.sub.2 and R.sub.3, which may be identical or different, denote hydrogen, C.sub.1 -C.sub.4 alkyl, carboxyl or alkoxycarbonyl; and X denotes hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.18 alkoxy, halogen or acetyl-amino; at least one of the groups X, R.sub.1, R.sub.2 and R.sub.3 being other than hydrogen; as well as the salts of these compounds;at least one oxidation dye precursor; andat least one oxidizing agent; is applied to said fibres, the pH of the composition applied to the fibres being less than 7.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: November 4, 1997
    Assignee: L'Oreal
    Inventors: Jean Cotteret, Marie Pascale Audousset
  • Patent number: 5645610
    Abstract: The new coupler compounds of the invention are 4-amino-2 -(2'-hydroxyethyl)-amino-5-methoxytoluene and/or 4-amino-2-(2'-hydroxyethyl)amino-5-chlorotoluene. The invention also includes an oxidation hair dye composition including an effective amount, advantageously from 0.01 to 5 percent by weight, of the above-mentioned new coupler compounds together with one or more known developer compounds and optionally certain direct dyes.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: July 8, 1997
    Inventors: Wolfgang R. Balzer, Anke Frank, Alexa Weinges
  • Patent number: 5637115
    Abstract: The oxidation hair dye composition consists of a combination of 0.01 to 10 percent by weight of one or more developer substances and 0.01 to 5 percent by weight of one or more coupler substances, and 0.01 to 2 percent by weight of one or more azo dye compounds of the formula I, A--N=N--B, wherein A is a p-aminophenyl group or a 3-pyridyl group and B is a 2,6-diamino-3-pyridyl group or a substituted 4-[N,N-bis-(2'-hydroxyethyl)amino]phenyl group of formula IV: ##STR1## wherein R is hydrogen, an alkyl group having from 1 to 6 carbon atoms, fluorine, chlorine, bromine or iodine; andone or more cosmetic additive selected from the group consisting of solvents, surfactants, antioxidants, thickeners, pH-adjusting compounds, hair care materials and additional dye components. The additional dye components can be 6-amino-2-methylphenol, 2-amino-5-methylphenol, triphenylmethane dye compounds and/or aromatic nitro dye compounds.
    Type: Grant
    Filed: January 16, 1996
    Date of Patent: June 10, 1997
    Assignee: Wella Aktiengesellschat
    Inventors: Wolfgang R. Balzer, Hans-Juergen Braun
  • Patent number: 5620484
    Abstract: A ready-to-use composition for the oxidation dyeing of keratin fibers, in particular human keratin fibers such as the hair, comprising, in an acidic medium (pH<7), at least one oxidation base in combination with at least one coupler selected from 6-hydroxyindoline and acid addition salts thereof and an oxidizing agent, as well as to the dyeing process using this composition.
    Type: Grant
    Filed: February 27, 1996
    Date of Patent: April 15, 1997
    Assignee: L'Oreal
    Inventor: Mireille Maubru
  • Patent number: 5616150
    Abstract: A composition for coloring keratin-containing fibers containing:(a) at least one isatin derivative corresponding to formula I: ##STR1## wherein R.sup.1 can represent hydrogen, a C.sub.1-4 alkyl group, a C.sub.2-4 hydroxyalkyl group, a C.sub.2-20 acyl group, a phenyl group, and a benzoyl group, and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 independently of one another can represent hydrogen, hydroxy, halogen, nitro groups, sulfo groups, carboxyl groups, C.sub.1-4 alkyl groups, C.sub.1-4 alkoxy groups or NR.sup.6 R.sup.7 groups and where R.sup.6 and R.sup.7 independently of one another represent hydrogen, C.sub.1-4 alkyl groups or C.sub.2-4 hydroxyalkyl groups, and wherein two adjacent groups R.sup.3, R.sup.4 and R.sup.
    Type: Grant
    Filed: October 30, 1995
    Date of Patent: April 1, 1997
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Hinrich Moeller, Horst Hoeffkes
  • Patent number: 5613985
    Abstract: The present invention relates to the use of a compound of the general formula I ##STR1## wherein R.sup.1 to R.sup.4, Hal and n are defined as in claim 1, as a coupler substance for the preparation of oxidation dyestuffs, and to hair colouring compositions which comprise a compound of the general formula I.
    Type: Grant
    Filed: September 22, 1995
    Date of Patent: March 25, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Bauer, Mustafa Akram