Aminoheterocyclic Dye Patents (Class 8/423)
  • 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: 5948121
    Abstract: The present invention relates to a permanent dyeing composition comprising a) above 0 to 1 mg enzyme protein per ml dyeing composition of microbial laccase, b) one or more dye precursor, and c) optionally one or more dye modifiers, the use of the dyeing composition for dyeing keratinous fibers, such as hair, fur, hide, and wool, and a method for permanent dyeing of keratinous fibers.
    Type: Grant
    Filed: May 22, 1998
    Date of Patent: September 7, 1999
    Assignee: Novo Nordisk A/S
    Inventors: Dorrit Aaslyng, Niels Henrik S.o slashed.rensen, Karen R.o slashed.rb.ae butted.k
  • 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: 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: 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: 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: 5858024
    Abstract: The invention relates to a composition, in particular a cosmetic composition, and more particularly one for dyeing keratin fibers, this composition containing at least one substance P antagonist in order to reduce or even eliminate the irritant effects of the dyes and/or pigments and/or dye precursors used during this dyeing. The substance P antagonist may form part of the dye composition itself or may be contained in a composition which is applied prior to the application of the dye composition.
    Type: Grant
    Filed: September 19, 1996
    Date of Patent: January 12, 1999
    Assignee: Societe L'Oreal S.A.
    Inventors: Olivier De Lacharriere, Lionel Breton, Genevieve Loussouarn
  • 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: 5827330
    Abstract: Water soluble, cationic products useful as hair colorants or for the treatment of skin which are esters or amides formed by reaction of melanin and a quaternary salt containing a reactive amino or hydroxyl group, as well as compositions containing them and methods of using such products to color hair or treat skin are described.
    Type: Grant
    Filed: June 13, 1997
    Date of Patent: October 27, 1998
    Assignee: Bristol-Myers Squibb Co.
    Inventors: Gottfried Wenke, Giuseppe Prota
  • 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: 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: 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: 5704949
    Abstract: The present invention is directed to the preparation of an aqueous hair dyeing composition containing an effective hair dyeing amount--at least 2 mg/ml--5,6-dihydroxyindole (DHI). An aqueous hair dyeing composition is produced by reacting under essentially anaerobic conditions dopa or a salt thereof with an alkali metal ferricyanide oxidant in an aqueous reaction medium to obtain dopachrome, and permitting the dopachrome to undergo rearrangement in the aqueous medium to form 5,6-dihydroxyindole, said rearrangement being conducted in the substantial absence of oxidant, the aqueous medium being buffered by sufficient buffering agent to maintain a pH of from about 4.5 to about 9 for the reaction medium throughout the series of reactions that take place thereafter, removing the ferrocyanide species present in the aqueous system, and lastly, charging the composition into a suitable container.
    Type: Grant
    Filed: February 16, 1996
    Date of Patent: January 6, 1998
    Assignee: Clairol Incorporated
    Inventors: Giuseppe Prota, Gottfried Wenke, Leszek Wolfram
  • 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: 5690697
    Abstract: A set for dyeing keratinous fibers, a dyeing composition, and a process for dyeing keratinous fibers using this dyeing composition are disclosed. Also disclosed is a multi-compartment device, or kit, one of the compartments of which contains the composition of the invention.
    Type: Grant
    Filed: July 20, 1995
    Date of Patent: November 25, 1997
    Assignee: L'Oreal
    Inventor: Henri Samain
  • 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: 5685882
    Abstract: A method for the dyeing of keratin fibers, and in particular human keratin fibers such as the hair, by applying to the fibers non-rinsed dye compositions containing guar gum as sole thickening agent.
    Type: Grant
    Filed: July 21, 1995
    Date of Patent: November 11, 1997
    Assignee: L'Oreal
    Inventors: Henri Samain, 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: 5645609
    Abstract: Process for the temporary dyeing of keratinous fibers with a composition containing an insoluble pigment obtained by the oxidative polymerization of an indole compound of formula (I) ##STR1## in which R.sup.1 and R.sup.3 are hydrogen or alkyl; R.sup.2 is hydrogen, alkyl carboxyl or alkoxy carbonyl; R.sup.4 and R.sup.7 are hydrogen, hydroxy, alkyl, amino, alkoxy, acyloxy or acylamino; R.sup.5 is hydrogen, hydroxy, alkoxy, alkyl, halogen, amino, acyloxy, acylamino or trimethylsilyloxy; R.sup.6 is hydrogen, hydroxy, alkoxy, amino, acyloxy, acylamino, trimethylsilyloxy or hydroxyalkylamino; R.sup.5 and R.sup.6 can also form, together with the carbon atoms to which they are attached, a carbonyl-dioxy ring; at least one of the radicals R.sup.4 to R.sup.7 is an OZ or NHR.sup.8 grouping, the R.sup.8 radical of the NHR.sup.8 grouping being hydrogen, acyl or hydroxyalkyl and the Z radical of the OZ grouping being hydrogen, acyl, alkyl or a trimethylsilyl group.
    Type: Grant
    Filed: March 18, 1996
    Date of Patent: July 8, 1997
    Assignee: L'Oreal
    Inventors: Herve Andrean, Alex Junino, Louis Lezoray, Jean Cotteret, Marie Pascale Audousset, Mireille Maubru
  • 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
  • Patent number: 5611817
    Abstract: A process for coloring keratin-containing fibers by contacting the fibers with a composition containing an isatin derivative corresponding to formula I: ##STR1## wherein R.sup.1 is hydrogen, a C.sub.1-4 alkyl group, a C.sub.2-4 hydroxyalkyl group, a C.sub.2-20 acyl group, a benzyl or phenyl group, R.sup.2 is hydrogen, a C.sub.1-4 alkyl group, a C.sub.1-4 alkoxy group, a hydroxy, halogen or nitro group, X is a sulfo group --SO.sub.3 H or a carboxyl group --COOH and n is an integer from 0 to 3, including water-soluble salts thereof.
    Type: Grant
    Filed: October 30, 1995
    Date of Patent: March 18, 1997
    Inventors: Hinrich Moeller, Horst Hoeffkes
  • Patent number: 5609649
    Abstract: Tinctorial composition for keratinous fibers, in particular for human hair, characterized in that it contains, in a medium appropriate for dyeing these fibers, at least one para oxidation dye precursor or at least one ortho oxidation dye precursor in combination with at least one heterocyclic coupler, corresponding to the formula: ##STR1## in which R.sub.1 denotes a hydrogen atom or a C.sub.1 -C.sub.4 alkyl radical; R.sub.2 denotes a hydrogen atom, a C.sub.1 -C.sub.4 lower alkyl radical, a carboxyl radical or an alkoxycarbonyl radical; R.sub.3 denotes a hydrogen or halogen atom, a C.sub.1 -C.sub.4 lower alkyl radical, a carboxyl radical, an alkoxycarbonyl radical or a formyl radical; X denotes a hydrogen atom, a C.sub.1 -C.sub.4 alkyl radical, a halogen atom, a C.sub.1 -C.sub.4 alkoxy radical, an acetylamino group or a dialkyl(C.sub.1 -C.sub.4)aminomethyl group; at least one of the groups X, R.sub.1, R.sub.2 and R.sub.3 differing from hydrogen; as well as their salts.
    Type: Grant
    Filed: June 20, 1994
    Date of Patent: March 11, 1997
    Assignee: L'Oreal
    Inventors: Alex Junino, Jean J. Vandenbossche, Herve Richard, Jean Cotteret
  • Patent number: 5609650
    Abstract: An oxidation dye composition for keratin fibers containing component A and component B wherein component A is an oxidation dye precursor indoline derivative of the formula I: ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.3 is hydrogen or an alkyl group having from 1 to 4 carbon atoms; each of R.sup.4 and R.sup.5 is hydrogen or an alkyl group having from 1 to 4 carbon atoms or together with the oxygen atom to which they are attached represent an alkylenedioxy group containing 1 to 4 carbon atoms; or a salt thereof; and wherein component B is a metal salt having a non-oxidizing anion selected from the group consisting of a lithium, magnesium, calcium, aluminum and a zinc salt.
    Type: Grant
    Filed: January 5, 1996
    Date of Patent: March 11, 1997
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Georg Knuebel, Horst Hoeffkes, Winifried Neuhaus, Edgar Lieske, deceased
  • Patent number: 5578087
    Abstract: Processes for the oxidative dyeing of keratinus fibers with compositions which comprise benzimidazole derivatives as couplers, at least one metaphenylenediaxnine and at least one para or ortho oxidation dye precursor, the benzimidazole derivative corresponding to the formula: ##STR1## in which: R.sub.1 represents a hydrogen atom or a C.sub.1 -C.sub.4 alkyl radical;R.sub.2 represents a hydrogen atom or a C.sub.1 -C.sub.4 alkyl radical or a phenyl radical;R.sub.3 represents a hydroxyl, amino or methoxy radical;R.sub.4 represents a hydrogen atom or a hydroxyl or methoxy or C.sub.1 -C.sub.4 alkyl radical;with the proviso that:when R.sub.3 denotes NH.sub.2, it occupies position 4;when R.sub.3 is at position 4, R.sub.4 is at position 7;when R.sub.3 is at position 5, then R.sub.4 is at position 6.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: November 26, 1996
    Assignee: L'Oreal
    Inventors: Marie P. Audousset, Jean Cotteret
  • Patent number: 5540738
    Abstract: A single-stage process for dyeing keratinous fibers in intense colors comprising simultaneously applying to said keratinous fibers a composition comprising iodide ions, an oxidant and an effective concentration of an oxidation dye to produce said intense colors when the pH of said composition is alkaline.
    Type: Grant
    Filed: March 13, 1995
    Date of Patent: July 30, 1996
    Inventors: Alexander C. Chan, David L. Chang, Yuh-Guo Pan
  • Patent number: 5538517
    Abstract: A method for dyeing keratin fibers by applying thereto: a component (1) consisting of an aqueous dyeing medium containing a compound of formula ##STR1## wherein R.sub.1 is hydrogen or alkyl; R.sub.2 is hydrogen, alkyl or COOH; R.sub.3 is hydrogen or alkyl; X is hydrogen, OH, NH.sub.2, alkyl or alkoxy; and Y is OH or NH.sub.2 ; a component (2) consisting of an aqueous dyeing medium containing a peroxidase enzyme; and a component (3) containing hydrogen peroxide or an enzymatic hydrogen peroxide source; said component (1) being applied first and separately from component (3).
    Type: Grant
    Filed: March 8, 1995
    Date of Patent: July 23, 1996
    Assignee: L'Oreal
    Inventors: Henri Samain, Claude Dubief
  • Patent number: 5518506
    Abstract: A process for dyeing keratinous fibres, wherein a mixture of at least one para-aminophenol of formula: ##STR1## in which, Y is oxygen or sulphur,R is alkyl, monohydroxyalkyl, polyhydroxyalkyl, or their acid addition salts, and 6-hydroxyindole, 7- hydroxyindole or mixtures thereof, is applied to the fibers, the colour being delayed at alkaline pH with an oxidising agent.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: May 21, 1996
    Assignee: L'Oreal
    Inventors: Jean Cotteret, Marie P. Audousset
  • Patent number: 5518505
    Abstract: Compositions for the oxidative dyeing of keratinous fibers comprising an indole derivative corresponding to the formula (I): ##STR1## in which: R.sub.1 denotes a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group, R.sub.2 and R.sub.3 denote a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group or a carboxyl or C.sub.1 -C.sub.4 alkoxycarbonyl group, R.sub.4 and R.sub.5, which are identical or different, denote a C.sub.1 -C.sub.4 alkyl group, a C.sub.2 -C.sub.20 acyl group, an aryl group, or else R.sub.4 and R.sub.5, together with the oxygen atoms and the two carbon atoms to which they are attached, form a ring optionally containing a carbonyl group or a methylene group unsubstituted or substituted by one or two alkyl or alkoxy or alkylamino groups, it being possible for R.sub.4 and R.sub.
    Type: Grant
    Filed: August 15, 1994
    Date of Patent: May 21, 1996
    Assignee: L'Oreal
    Inventor: Jean Cotteret
  • Patent number: 5494490
    Abstract: Processes for the dyeing of keratinous fibers with compositions which contain 4-hydroxy- or 4-aminobenzimidazole or their derivatives corresponding to the formula (I): ##STR1## in which: R.sub.1 and R.sub.2 represent hydrogen or alkyl, one at least of the substituents being equal to hydrogen,R.sub.3 denotes OH or NH.sub.2,as coupler for dyeing keratinous fibers, in particular hair, in the presence of a p-phenylenediamine, the ratio between the p-phenylenediamine and the coupler of formula (I) being greater than or equal to 1.2.
    Type: Grant
    Filed: November 19, 1993
    Date of Patent: February 27, 1996
    Assignee: L'Oreal
    Inventors: Marie P. Audousset, Jean Cotteret
  • Patent number: 5492541
    Abstract: A process for preparing dye compositions which comprises hydrolyzing an O-protected 5,6-dihydroxyindole with an alkaline material under substantially anaerobic condition and the products made by such process.
    Type: Grant
    Filed: January 5, 1990
    Date of Patent: February 20, 1996
    Assignee: Clairol Incorporated
    Inventors: Bryan P. Murphy, Keith C. Brown, Thomas M. Schultz, Alice A. Meyer
  • Patent number: 5480460
    Abstract: A dye concentrate for dyeing keratin fibers which comprises the following components (A), (B) and (C):(A) 10% by weight or more, based on the total weight of the composition, of an oxidation dye having two or more amino groups per molecule in the non-salt form or salt free;(B) 0.5% by weight or more, based on the total weight of the composition, of an inorganic or organic reducing agent; and(C) water or an organic solvent;and a dye composition for dyeing keratin fibers containing the same are disclosed. The dye concentrate of the present invention remains stable even when stored for a long time and can be easily formulated into a dye composition at use.
    Type: Grant
    Filed: August 18, 1994
    Date of Patent: January 2, 1996
    Assignee: Kao Corporation
    Inventor: Tsutomu Muraoka
  • Patent number: 5478360
    Abstract: Process for preserving the dyeing capacity of 5,6-dihydroxyindole or of its derivatives corresponding to the formula (I): ##STR1## in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which are identical or different, denote hydrogen or a C.sub.1 -C.sub.4 lower alkyl, R.sub.1, R.sub.2 and R.sub.3 denoting hydrogen when R.sub.4 denotes alkyl in an aqueous medium, characterized in that the pH of the aqueous medium is adjusted to a value pH.sub.C of between 5 and 10 by employing a pH-regulating agent containing two components (A) and (B), the component (A) being chosen from pH-regulating agents which have a dissociation constant K.sub.CA in aqueous solution at 25.degree. C., such as pk.sub.CA, that is:0<pk.sub.CA -pH.sub.C .ltoreq.2.5and the component (B) being chosen from pH-regulating agents which have a dissociation constant K.sub.CB in aqueous solution at 25.degree. C., such as pk.sub.CB, that is:2<pk.sub.CB <pH.sub.C.
    Type: Grant
    Filed: February 17, 1995
    Date of Patent: December 26, 1995
    Assignee: L'Oreal
    Inventors: Jean F. Grollier, Marie F. Bosq, Jean Cotteret, Arnaud De Labbey
  • Patent number: 5451254
    Abstract: The invention relates to a dispersion of melanic pigments containing in a medium selected amongst: a) the straight or branched monoalcohols comprising at least 3 carbon atoms; the straight or branched polyols comprising at least 2 carbon atoms; the saturated or unsaturated cycloaliphatic alcohols comprising at least 6 carbon atoms; the aromatic alcohols comprising at least 6 carbon atoms; the C.sub.8 -C.sub.22 fatty acid esters and C.sub.1 -C.sub.6 alcohol esters or the C.sub.2 -C.sub.6 polyol esters; the C.sub.1 -C.sub.6 aliphatic acid esters or the C.sub.8 -C.sub.22 aromatic acid and fatty alcohol esters; the C.sub.8 -C.sub.22 fatty acid esters and the C.sub.8 -C.sub.22 fatty alcohol esters, the C.sub.6 -C.sub.
    Type: Grant
    Filed: September 19, 1994
    Date of Patent: September 19, 1995
    Assignee: L'Oreal
    Inventors: Herve Andrean, Didier Candau, Myrian Mellul, Christos Papantoniou, Bertrand Piot
  • Patent number: 5449403
    Abstract: A product in the form of colored inorganic particles including one or a number of melanin pigments, a process for its preparation and to its use, especially in the field of cosmetics, for make-up for the exoskeleton and/or for the skin, and in protecting human skin against UV radiation.
    Type: Grant
    Filed: January 3, 1994
    Date of Patent: September 12, 1995
    Assignee: L'Oreal
    Inventors: Herve Andrean, Alex Junino, Jean P. Arraudeau
  • Patent number: 5427588
    Abstract: The invention relates to indoline compounds of formula (I): ##STR1## in which: R.sub.1 and R.sub.2 denote hydrogen, alkyl, monohydroxyalkyl, polyhydroxyalkyl, nitro, hydroxyl, alkoxy or NHR where R can be hydrogen, alkyl, monohydroxyalkyl or polyhydroxyalkyl;X denotes oxygen or sulfur;R.sub.3 represents --OR.sub.4 or NR.sub.5 R.sub.6 whereR4 denotes alkyl, alkenyl, benzyl, alkoxyalkyl or haloalkyl;R.sub.5 and R.sub.6 denote alkyl;R.sub.1 and R.sub.2 not simultaneously denoting hydrogen or nitro and when R.sub.1 denotes alkyl, alkoxy or mono- or polyhydroxyalkyl, R.sub.2 denotes NHR or hydroxyl,and to their use in dyeing keratinous fibers.
    Type: Grant
    Filed: December 14, 1993
    Date of Patent: June 27, 1995
    Assignee: L'Oreal
    Inventors: Alain Lagrange, Jean J. Vandenbosche, Herve Andrean