WO2008028895A1 - Diminution du vieillissement capillaire - Google Patents

Diminution du vieillissement capillaire Download PDF

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Publication number
WO2008028895A1
WO2008028895A1 PCT/EP2007/059202 EP2007059202W WO2008028895A1 WO 2008028895 A1 WO2008028895 A1 WO 2008028895A1 EP 2007059202 W EP2007059202 W EP 2007059202W WO 2008028895 A1 WO2008028895 A1 WO 2008028895A1
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Prior art keywords
hair
amino
group
alkyl group
carnitine
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PCT/EP2007/059202
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German (de)
English (en)
Inventor
Astrid Kleen
Mustafa Akram
Melanie Giesen
Elisabeth Poppe
Edo Hoting
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Henkel Ag & Co. Kgaa
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Publication of WO2008028895A1 publication Critical patent/WO2008028895A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q7/00—Preparations for affecting hair growth
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/14—Drugs for dermatological disorders for baldness or alopecia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair

Definitions

  • the present invention relates to the use of quaternized beta-hydroxybutyric acid derivatives to compensate for the hair aging agent caused by premature aging or dying of hair.
  • Human hair is today treated in a variety of ways with hair cosmetic preparations. These include, for example, the cleansing of hair with shampoos, the care and regeneration with rinses and cures, and the bleaching, dyeing and shaping of the hair with bleaching agents, dyes, tinting agents, waving agents and styling preparations. In this case, means for changing the color of the head hair, as well as the deformation of the hair play a prominent role.
  • oxidation colorants For permanent, intensive colorations with corresponding fastness properties, so-called oxidation colorants are used.
  • Such hairline colorants usually contain oxidation dye precursors, so-called developer components and coupler components.
  • the developer components form the actual dyes under the influence of oxidizing agents or of atmospheric oxygen with one another or with coupling with one or more coupler components.
  • the oxidation dyes are characterized by excellent, long-lasting dyeing results. For naturally acting dyeings but usually a mixture of a larger number of oxidation dye precursors must be used; In many cases, direct dyes are still used for shading.
  • the developer components are usually primary aromatic amines having a further, in the para or ortho position, free or substituted hydroxy or amino group, Diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and its derivatives used.
  • coupler components m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols are generally used.
  • Suitable coupler substances are, in particular, 1-naphthol, 1,5-dihydroxynaphthalene, 2,7-dihydroxynaphthalene and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monoethyl ether, m-phenylenediamine, 1 -Phenyl-3-methyl-pyrazolone-5, 2,4-dichloro-3-aminophenol, 1,3-bis (2,4-diaminophenoxy) -propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6 -methyl-3-aminophenol, 2-methylresorcinol, 5-methylre
  • dyeing or tinting agents which contain so-called direct drawers as a coloring component. These are dye molecules that grow directly on the hair and do not require an oxidative process to form the color. These dyes include, for example, the henna already known from antiquity for coloring body and hair. These dyeings are generally much more sensitive to shampooing than the oxidative dyeings, so that a much more undesirable nuance shift or even a visible "discoloration" occurs much more quickly.
  • One way to stain keratinous fibers is to use stains that contain a combination of component
  • component B compounds selected from (a) CH-acidic compounds and (b) compounds having primary or secondary amino group or hydroxy group selected from primary or secondary aromatic amines, nitrogen-containing heterocyclic compounds and aromatic hydroxy compounds
  • the corresponding dyeing method (referred to below as oxo dyeing) is described, for example, in the publications WO-A1-99 / 18916, WO-A1 -00 / 38638, WO-A1-01 / 34106 and WO-A1-01 / 47483.
  • the resulting dyeings have partially color fastness on the keratin-containing fiber, which are comparable to those of the oxidation dyeing.
  • the Nuancenspektrum achievable with the gentle oxo staining is very broad and the color obtained often has an acceptable brilliance and color depth.
  • the aforementioned components A and B hereinafter referred to as Oxofarbstoffvor area, are generally not themselves dyes, and are therefore each alone taken not for coloring keratin-containing fibers. In combination, they form dyes in a non-oxidative process.
  • the oxo staining method can be readily combined with the oxidative staining system.
  • dyes obtained should have a high degree of color fastness, for example, to washing, light or friction, and in particular must be compatible with other hair treatment preparations in the context of hair care.
  • oxidative color change agents should protect the hair structure.
  • a permanent deformation keratin braver fibers is usually carried out by mechanically deforming the fiber and determines the deformation by suitable means.
  • the fiber Before and / or after this deformation, the fiber is treated with a keratin-reducing preparation. After a rinsing process, the fiber is then treated with an oxidizing agent preparation, rinsed and freed from the deformation aids (winders, papillots).
  • a mercaptan eg ammonium thioglycolate
  • it splits a part of the disulfide bridges of the keratin molecule into -SH groups, so that the keratin fibers are softened.
  • disulfide bridges are knotted in the hair keratin, so that the Keratingeglage is fixed in the predetermined deformation.
  • Hydrogen sulfite, sulfite or disulfite containing reducing agents do not have the strong odor of the mercaptan-containing agents.
  • the cleavage can be reversed as described above in a fixing step using an oxidizing agent to form new disulfide bridges.
  • the Applicant's latest research has shown that the energy balance of the hair root (hair follicles) is reduced during hair treatment, in particular due to the influence of oxidizing agents, such as peroxides.
  • the energy balance of hair follicles is represented by the content of adenosine 5'-triphosphate (ATP).
  • ATP adenosine 5'-triphosphate
  • the apoptosis of the hair follicle cells ie the programmed cell death of the hair follicle cells can be promoted by the action of oxidant-containing cosmetics as a stress factor.
  • the programmed cell death first manifests itself in morphological changes such as the shrinkage of the cells.
  • a fragmentation of the chromosomal DNA shows up and it ultimately comes to the death and degradation of the affected cells.
  • necrosis apoptosis is actively performed by the cell itself and is part of the metabolism of the cell. As a result, this form of cell death is subject to strict control and it is ensured that the cell in question is destroyed without damaging the neighboring tissue.
  • the triggers of apoptosis are intrinsic or extrinsic signals, such as tumor necrosis factor alpha (TNF), so-called “death factors” or genotoxic substances, and central regulators of apoptosis are caspases belonging to the family of cysteine proteases or the antagonists Bax and Bcl
  • This group of proteins, commonly referred to as the Bcl-2 family can be divided into two groups, an anti-apoptotic (Bcl-2, Bcl-xL, Bcl-w, Mcl-1, etc.) and a pro-apoptotic (Bax, Bak, Bad, Bcl-xS, Bik, Bid), with Bax and Bcl-2 representing the two major representatives (for a review of apoptotic processes in the cell, see Figure 1), and normally both groups are in equilibrium. If the ratio of Bax and Bcl-2 shifts, there are changes in the cell. For example, the increased expression of Bax leads to increased apoptos
  • apoptosis plays a role, especially in the hair cycle, since the regression phase of the follicle, which precedes the subsequent resting phase and rejection of the hair, is initiated by apoptosis. Also in the hair follicle, apoptosis is controlled by various factors, including TGFbI (transforming growth factor beta 1), Bax / Bcl2 or various caspases play a role. In addition to the naturally occurring apoptosis in the normal hair cycle of humans, apoptosis is also discussed in connection with increased hair loss. Various triggers (hereditary, stress factors, etc.) can lead to increased apoptosis in the hair follicle, and thus the regression phase and thus ultimately the ejection of the hair is prematurely initiated.
  • TGFbI transforming growth factor beta 1
  • Bax / Bcl2 transforming growth factor beta 1
  • caspases caspases
  • Oxidative stress can also induce apoptosis in cells.
  • cyclooxygenase-2 (Cox2) plays a role in this process as a mediator.
  • the effect of oxidative stress is discussed, for example as a cause of hair graying, as oxidative stress can lead to apoptosis in the hair follicle melanocytes.
  • Further effects of oxidative Stress, especially in the hair follicle, has not yet been studied, but there is no evidence that the hair follicle has a special protective mechanism that protects it from stress factors, such as oxidative stress, so that it can be assumed that the biologically active hair follicle cells, like other cells, can be damaged by oxidative stress.
  • the Applicant has now surprisingly found that the use of quaternized beta-hydroxybutyric acid derivatives protects the hair follicle cells from premature apoptosis induced by stress factors, such as oxidative stress, UV radiation, aging processes, stress by a non-physiological pH , The protection against oxidative stress occurs even during the oxidative hair treatment.
  • stress factors such as oxidative stress, UV radiation, aging processes, stress by a non-physiological pH
  • a first subject of the invention is therefore the cosmetic use of at least one compound according to formula (I)
  • R 1 , R 2 and R 3 independently of one another represent a C 1 - to C 4 -alkyl group or a C 2 - to C 4 -
  • R 4 is a hydrogen atom, a C 1 - to C 4 -alkyl group or a C 2 - to C 6 -
  • R 5 is a hydrogen atom, a negative charge or a C 1 - to C 4 alkyl group, to protect the hair, especially the hair follicle cells, from stress factors.
  • Stress factors in the sense of the inventions are those internal or external factors or stimuli which initiate premature apoptosis.
  • the effect of stress factors (such as the effect of oxidative stress, caused for example by free radicals), stress due to UV radiation, stress due to aging processes, mental stress or stress due to non-physiological pH values) on the metabolism of the hair Hair follicle cells, is prevented by the use of the invention or reduced. In doing so, the favored or accelerated apoptosis of the hair follicle cells is prevented or reduced. The premature death of the hair or premature failure of the hair, which is promoted by stress factors, is prevented or reduced in this way.
  • stress factors such as the effect of oxidative stress, caused for example by free radicals
  • stress due to UV radiation stress due to aging processes
  • mental stress or stress due to non-physiological pH values on the metabolism of the hair Hair follicle cells
  • the compounds of the formula (I) preferably have a molecular weight of less than 500 g / mol, more preferably less than 400 g / mol.
  • the cosmetic treatment is preferably carried out by topical application of cosmetic compositions containing at least one compound according to formula (I).
  • radicals R 1 , R 2 and R 3 are preferably, independently of one another, a methyl or an ethyl group, particularly preferably a methyl group.
  • the radical R 4 is preferably a hydrogen atom or a C 2 to C 4 acyl group.
  • a preferred C 2 to C 4 acyl group is the acetyl group.
  • the compounds of formula (I) are in the form of an inner salt.
  • R 5 is a hydrogen atom or a C 1 -C 4 -alkyl group
  • the compound of the formula (I) is in the form of a salt with a physiologically tolerable anion X " as counterion. I).
  • the physiologically acceptable anions X ' must not only carry a negative charge, but may also have a charge number greater than one. In the latter case, the anions X 'of the salt form are described to maintain electroneutrality by formulating a stoichiometric coefficient of less than 1 before the name of the anion.
  • the physiologically acceptable anions are preferably selected from halide, 0.5 sulfate, hydrogen sulfate, 0.5 carbonate, bicarbonate, 1/3 phosphate, 0.5 hydrogen phosphate, dihydrogen phosphate, carboxylate, such as lactate, citrate or tartrate.
  • X ' particularly preferably represents chloride, bromide or a carboxylate counterion, in particular lactate, citrate or tartrate.
  • the beta carbon atom of the butyric acid skeleton of the compounds of the formula (I) is chiral.
  • the subject matter of the invention relates both to compounds of the formula (I) in Configuration, as well as compounds of formula (I) in D configuration and mixtures of both configurations, such as racemates.
  • Examples of a (C 2 - to C 4 ) -hydroxyalkyl group of the formula (I) are 2-hydroxyethyl, 2-
  • Examples of a (C 1 - to C 4 ) -alkyl group of the formula (I) are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.
  • Examples of a (C 2 - to C 6 ) -acyl group of the formula (I) are acetyl, propionyl, butyryl and
  • the compound of the formula (I) used according to the invention is preferably at least one compound selected from the group consisting of L-carnitine, D-carnitine, D, L-carnitine, L-carnitine tartrate, D-carnitine tartrate, D, L-carnitine tartrate , L-carnitine lactate, D-carnitine lactate, D, L-carnitine lactate, L-carnitine citrate, D-carnitine citrate, D, L-carnitine citrate, L-acetyl carnitine, D-acetyl carnitine and D, L-acetyl carnitine.
  • the use according to the invention of the compounds of the formula (I) according to the first subject of the invention preferably takes place i) before, during or subsequent to an oxidative hair treatment and / or ii) before, during or subsequent to a hair treatment at non-physiological pH values, in particular of pH values greater than pH 7.4, in particular greater than pH 8, instead.
  • the physiological pH is by definition in a pH range of pH 7.4 to 5.5.
  • following to a hair treatment means at intervals of up to 12 hours, preferably directly following said hair treatment
  • the use of the first subject of the invention is not therapeutic.
  • a second object of the invention is the use of at least one compound according to formula (I),
  • R 1 , R 2 and R 3 independently of one another represent a C 1 - to C 4 -alkyl group or a C 2 - to C 4 -
  • R 4 is a hydrogen atom, a C 1 - to C 4 -alkyl group or a C 2 - to C 6 -
  • R 5 represents a hydrogen atom, a negative charge or a C 1 - to C 4 alkyl group, for the preparation of an agent for protecting the hair, in particular the hair follicle cells, from stress factors.
  • a third object of the invention is the use of at least one compound according to formula (I),
  • R 1 , R 2 and R 3 independently of one another represent a C 1 - to C 4 -alkyl group or a C 2 - to C 4 -
  • R 4 is a hydrogen atom, a C 1 - to C 4 -alkyl group or a C 2 - to C 6 -
  • R 5 represents a hydrogen atom, a negative charge or a C 1 - to C 4 alkyl group, for the preparation of an agent for protecting against stress factors favored, premature hair loss.
  • the compounds of the formula (I) are preferably in an amount of 0.001 to 10 wt .-%, particularly preferably from 0.01 to 5 wt .-%, most preferably from 0.1 to 2 wt .-%, respectively based on the weight of the ready-to-use agent, contained in the funds.
  • the agents additionally contain at least one color changing component.
  • the color changing component is preferably selected
  • developer components are usually primary aromatic amines with another, in the para or ortho position, free or substituted hydroxy or amino group, diaminopyridine, heterocyclic hydrazones, 4-aminopyrazole derivatives and 2,4,5,6-tetraaminopyrimidine and its derivatives used ,
  • p-phenylenediamine derivatives of the formula (Ent1) it may be preferred according to the invention to use as the developer component a p-phenylenediamine derivative or one of its physiologically acceptable salts. Particular preference is given to p-phenylenediamine derivatives of the formula (Ent1) ) in which
  • G 1 represents a hydrogen atom, a C 1 - to C 4 alkyl, C 1 - to C 4 - monohydroxyalkyl radical, a C 2 - to C 4 polyhydroxyalkyl radical, a (C 1 - to C 4) alkoxy ( C 1 -C 4 ) -alkyl radical, a 4'-aminophenyl radical or a C 1 -C 4 -alkyl radical which is substituted by a nitrogen-containing group, a phenyl or a 4'-aminophenyl radical;
  • G 2 represents a hydrogen atom, a C 1 - to C 4 alkyl, C 1 - to C 4 - monohydroxyalkyl radical, a C 2 - to C 4 polyhydroxyalkyl radical, a (C 1 - to C 4) alkoxy ( C 1 -C 4 ) -alkyl radical or a C 1 -C 4 -alkyl radical which is substituted by a nitrogen-containing group
  • G 3 represents a hydrogen atom, a halogen atom such as a chlorine, bromine, iodine or fluorine atom, a C 1 - to C 4 -alkyl radical, a C 1 - to C 4 -monohydroxyalkyl radical, a C 2 - to C 4 Polyhydroxyalkyl, C 1 to C 4 hydroxyalkoxy, C 1 to C 4 acetylaminoalkoxy, C 1 to C 4 mesylaminoalkoxy or C 1 to C 4 carbamoylaminoalkoxy;
  • a halogen atom such as a chlorine, bromine, iodine or fluorine atom
  • a C 1 - to C 4 -alkyl radical such as a chlorine, bromine, iodine or fluorine atom
  • a C 1 - to C 4 -alkyl radical such as a chlorine, bromine, iodine or fluorine atom
  • G 4 represents a hydrogen atom, a halogen atom or a C 1 - to C 4 -alkyl radical or when G 3 and G 4 are ortho to each other, they may together form a bridging ⁇ , ⁇ -alkylenedioxy group, such as, for example, an ethylenedioxy group.
  • C 1 - to C 4 -alkyl radicals mentioned as substituents in the compounds according to the invention are the groups methyl, ethyl, propyl, isopropyl and butyl. Ethyl and methyl are preferred alkyl radicals.
  • C 1 -C 4 -alkoxy radicals preferred according to the invention are, for example, a methoxy or an ethoxy group.
  • a C 1 - to C 4 -hydroxyalkyl group a hydroxymethyl, a 2-hydroxyethyl, a 3-hydroxypropyl or a 4-hydroxybutyl group may be mentioned.
  • a 2-hydroxyethyl group is particularly preferred.
  • a particularly preferred C 2 to C 4 polyhydroxyalkyl group is the 1, 2-dihydroxyethyl group.
  • halogen atoms are according to the invention F, Cl or Br atoms, Cl atoms are very particularly preferred.
  • the other terms used are derived according to the invention from the definitions given here.
  • nitrogen-containing groups of the formula (Ent1) are in particular the amino groups, C 1 - to C 4 -monoalkylamino groups, C 1 - -C 4 -dialkylamino, C 1 - to C 4 -Trialkylammonium phenomenon, C 1 - to C 4 - Monohydroxyalkylamino phenomenon, imidazolinium and ammonium.
  • Particularly preferred p-phenylenediamines of the formula (Ent1) are selected from p-phenylenediamine, p-toluenediamine, 2-chloro-p-phenylenediamine, 2,3-dimethyl-p-phenylenediamine, 2,6-dimethyl-p-phenylenediamine, 2 , 6-diethyl-p-phenylenediamine, 2,5-dimethyl-p-phenylenediamine, N, N-dimethyl-p-phenylenediamine, N, N-diethyl-p-phenylenediamine, N, N-dipropyl-p-phenylenediamine, 4 -Amino-3-methyl- (N, N-diethyl) -aniline, N, N-bis- ( ⁇ -hydroxyethyl) -p-phenylenediamine, 4-N, N-bis- ( ⁇ -hydroxyethyl) amino-2- methylaniline, 4-N,
  • Very particular preferred p-phenylenediamine derivatives of the formula (Ent1) according to the invention are p-phenylenediamine, p-toluenediamine, 2- ( ⁇ -hydroxyethyl) -p-phenylenediamine, 2- ( ⁇ , ⁇ -dihydroxyethyl) -p-phenylenediamine and N, N bis (.beta.-hydroxyethyl) -p-phenylenediamine.
  • developer component compounds which contain at least two aromatic nuclei which are substituted by amino and / or hydroxyl groups.
  • binuclear developer components that can be used in the compositions according to the invention, mention may be made in particular of the compounds which correspond to the following formula (Ent2) and their physiologically tolerated salts:
  • Z 1 and Z 2 independently of one another represent a hydroxyl or NH 2 radical which is optionally substituted by a C 1 - to C 4 -alkyl radical, by a C 1 - to C 4 -hydroxyalkyl radical and / or by a bridge Y.
  • the bridge Y is an alkylene group having 1 to 14 carbon atoms, such as a linear or branched alkylene chain or an alkylene ring, which is one or more nitrogen-containing groups and / or one or more heteroatoms such as oxygen , Sulfur or nitrogen atoms may be interrupted or terminated and may possibly be substituted by one or more hydroxyl or C 1 - to C 8 -alkoxy radicals, or a direct bond,
  • G 5 and G 6 independently of one another represent a hydrogen or halogen atom, a C 1 - to C 4 -alkyl radical, a C 1 - to C 4 -monohydroxyalkyl radical, a C 2 - to C 4 -hydroxyalkyl radical, a C 1 - to C 4 -aminoalkyl radical or a direct compound for bridging Y,
  • G 7 , G 8 , G 9 , G 10 , G 11 and G 12 independently represent a hydrogen atom, a direct bond to the bridge Y or a C 1 - to C 4 -alkyl radical, with the provisos that the compounds of the formula (Ent2) contain only one bridge Y per molecule and the compounds of the formula (Ent2) contain at least one amino group which carries at least one hydrogen atom.
  • Preferred binuclear developer components of the formula (Ent2) are in particular: N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) -1,3-diamino-propan-2-ol, N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) ethylenediamine, N, N'-bis (4-aminophenyl) tetramethylenediamine, N, N'- Bis ( ⁇ -hydroxyethyl) -N, N'-bis (4-aminophenyl) tetramethylenediamine, N, N'-bis (4-methylaminophenyl) tetramethylenediamine, N, N'-diethyl-N, N 'bis (4'-amino-3'-methylphenyl) ethylenediamine, bis (2-hydroxy-5-aminophenyl) methane, 1,3-
  • Very particularly preferred binuclear developer components of the formula (Ent2) are N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) -1,3-diamino-propan-2-ol, Bis (2-hydroxy-5-aminophenyl) methane, 1, 3-bis (2,5-diaminophenoxy) -propan-2-ol, N, N'-bis (4'-aminophenyl) -1, 4-diazacycloheptane and 1, 10-bis (2 ', 5'-diaminophenyl) -1, 4,7,10-tetraoxadecan or one of its physiologically acceptable salts.
  • p-aminophenol derivatives of the formula (Ent3) it may be preferred according to the invention to use as the developer component a p-aminophenol derivative or one of its physiologically tolerable salts. Particular preference is given to p-aminophenol derivatives of the formula (Ent3)
  • G 13 represents a hydrogen atom, a halogen atom, a C 1 - to C 4 -alkyl radical, a C 1 - to
  • (C 1 - to C 4) alkyl group a C 1 - to C 4 aminoalkyl radical, a hydroxy (C- ⁇ - to C 4) - alkylamino, C 1 - to C 4 -Hydroxyalkoxyrest, a C 1 - to C 4 -hydroxyalkyl- (C-1 bis
  • G 14 is a hydrogen or halogen atom, a C 1 - to C 4 -alkyl radical, a C 1 - to C 4 -
  • Monohydroxyalkyl radical a C 2 - to C 4 -polyhydroxyalkyl radical, a (C 1 - to C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl radical, a C 1 - to C 4 -aminoalkyl radical or a C 1 - to C 4 -Cyanoalkylrest,
  • G 15 is hydrogen, C 1 - to C 4 -alkyl, C 1 - to C 4 -monohydroxyalkyl, C 2 - to C 4 -polyhydroxyalkyl, phenyl or benzyl, and
  • G 16 is hydrogen or a halogen atom.
  • the substituents used in formula (Ent3) are defined according to the invention analogously to the above statements.
  • Preferred p-aminophenols of the formula (Ent3) are, in particular, p-aminophenol, N-methyl-p-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 2-hydroxymethylamino-4-aminophenol, 4 -Amino-3-hydroxymethylphenol, 4-amino-2- ( ⁇ -hydroxyethoxy) -phenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethyl-phenol, 4-amino -2-aminomethylphenol, 4-amino-2- ( ⁇ -hydroxyethyl-aminomethyl) phenol, 4-amino-2- ( ⁇ , ⁇ -dihydroxyethyl) phenol, 4-amino-2-fluorophenol, 4-amino-2 -chlorophenol, 4-amino-2,6-dichlorophenol, 4-amino-2- (diethyl-aminomethyl) -phenol and their physiological
  • Very particularly preferred compounds of the formula (Ent3) are p-aminophenol, 4-amino-3-methylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- ( ⁇ , ⁇ -dihydroxyethyl) phenol and A-amino 2- (diethylaminomethyl) -phenol.
  • the developer component may be selected from o-aminophenol and its derivatives such as 2-amino-4-methylphenol, 2-amino-5-methylphenol or 2-amino-4-chlorophenol.
  • the developer component may be selected from heterocyclic developer components, such as the pyridine, pyrimidine, pyrazole, pyrazole pyrimidine derivatives and their physiologically acceptable salts.
  • Preferred pyridine derivatives are, in particular, the compounds described in the patents GB 1 026 978 and GB 1 153 196, such as 2,5-diamino-pyridine, 2- (4'-methoxyphenyl) amino-3-amino-pyridine, 2,3-diamino-6-methoxy-pyridine, 2- ( ⁇ -methoxyethyl) amino-3-amino-6-methoxy-pyridine and 3,4-diamino-pyridine.
  • Preferred pyrimidine derivatives are, in particular, the compounds described in German Patent DE 2 359 399, Japanese Laid-Open Patent Publication JP 02019576 A2 or in the published patent application WO 96/15765, such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy- 2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2-dimethylamino-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6- triaminopyrimidine.
  • Preferred pyrazole derivatives are, in particular, the compounds described in patents DE 3 843 892, DE 4 133 957 and patent applications WO 94/08969, WO 94/08970, EP-740 931 and DE 195 43 988, such as 4,5 Diamino-1-methylpyrazole, 4,5-diamino-1- ( ⁇ -hydroxyethyl) pyrazole, 3,4-diaminopyrazole, 4,5-diamino-1- (4'-chlorobenzyl) pyrazole, 4.5- Diamino-1, 3-dimethylpyrazole, 4,5-diamino-3-methyl-1-phenylpyrazole, 4,5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1,3-dimethyl-5-hydrazinopyrazole, 1-Benzyl-4,5-diamino-3-methylpyrazole, 4,5-diamino-3-tert-butyl-1
  • Triaminopyrazole 1-methyl-3,4,5-triaminopyrazole, 3,5-diamino-1-methyl-4-methylaminopyrazole and 3,5-diamino-4- ( ⁇ -hydroxyethyl) amino-1-methylpyrazole.
  • Preferred pyrazolopyrimidine derivatives are, in particular, the derivatives of the pyrazolo [1,5-a] opyrimidine of the following formula (Ent4) and their tautomeric forms, if a tautomeric equilibrium exists:
  • G 17 , G 18 , G 19 and G 20 independently of one another represent a hydrogen atom, a C 1 - to C 4 -alkyl radical, an aryl radical, a C 1 - to C 4 -hydroxyalkyl radical, a C 2 - to C 4 - Polyhydroxyalkylrest a (C 1 - to C 4 ) -alkoxy- (C-
  • - to C 4 ) -alkyl radical, a C 1 - to C 4 - aminoalkyl radical, optionally protected by an acetyl-ureide or a sulfonyl radical may be a (C 1 - to C 4 ) -alkylamino- (C- ⁇ - to C 4 ) -alkyl radical, a di - [(C- ⁇ - to C 4 ) alkyl] - (C- ⁇ - bis C 4 ) -aminoalkyl radical, where the dialkyl radicals optionally form a carbon cycle or
  • Group OH occupy the positions (2,3); (5,6); (6,7); (3,5) or (3,7);
  • pyrazolo [1, 5-a] pyrimidines of the above formula (Ent4) can be prepared as described in the literature by cyclization from an aminopyrazole or hydrazine.
  • m-phenylenediamine derivatives naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenol derivatives and heterocyclic compounds are generally used.
  • Preferred coupler components according to the invention are m-aminophenol and its derivatives, such as, for example, 5-amino-2-methylphenol, N-cyclopentyl-3-aminophenol, 3-amino-2-chloro-6-methylphenol, 2-hydroxy-4-aminophenoxyethanol, 2 6-Dimethyl-3-aminophenol, 3-trifluoroacetylamino-2-chloro-6-methylphenol, 5-amino-4-chloro-2-methylphenol, 5-amino-4-methoxy-2-methylphenol, 5- (2'- Hydroxyethyl) amino-2-methylphenol, 3- (diethylamino) -phenol, N-cyclopentyl-3-aminophenol, 1,3-dihydroxy-5- (methylamino) -benzene, 3-ethylamino-4-methylphenol and 2,4 Dichloro-3-aminophenol, o-aminophenol and its derivatives, m-diaminobenzene and its derivatives such as
  • Di- or trihydroxybenzene derivatives such as resorcinol, resorcinol monomethyl ether, 2-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol, 2-chlororesorcinol, 4-chlororesorcinol, pyrogallol and 1,2,4-trihydroxybenzene, pyridine derivatives such as 2,6-dihydroxypyridine , 2-amino-3-hydroxypyridine, 2-amino-5-chloro-3-hydroxypyridine, 3-amino-2-methylamino-6-methoxypyridine, 2,6-dihydroxy-3,4-dimethylpyridine, 2,6-dihydroxy 4-methylpyridine, 2,6-diaminopyridine, 2,3-diamino-6-methoxypyridine and 3,5-diamino-2,6-dimethoxypyridine,
  • Naphthalene derivatives such as 1-naphthol, 2-methyl-1-naphthol, 2-hydroxymethyl-1-naphthol, 2-hydroxyethyl-1-naphthol, 1, 5-dihydroxynaphthalene, 1, 6-dihydroxynaphthalene, 1, 7-dihydroxynaphthalene, 1 , 8-dihydroxynaphthalene, 2,7-dihydroxynaphthalene and 2,3-dihydroxynaphthalene,
  • Morpholine derivatives such as 6-hydroxybenzomorpholine and 6-aminobenzomorpholine,
  • Quinoxaline derivatives such as 6-methyl-1,2,3,4-tetrahydroquinoxaline, pyrazole derivatives such as 1-phenyl-3-methylpyrazol-5-one, indole derivatives such as 4-hydroxyindole, 6-hydroxyindole and 7-hydroxyindole, pyrimidine derivatives such as For example, 4,6-diaminopyrimidine, 4-amino-2,6-dihydroxypyrimidine, 2,4-diamino-6-hydroxypyrimidine, 2,4,6-trihydroxypyrimidine, 2-amino-4-methylpyrimidine, 2-amino-4-hydroxy 6-methylpyrimidine and 4,6-dihydroxy-2-methylpyrimidine, or methylenedioxybenzene derivatives such as, for example, 1-hydroxy-3,4-methylenedioxybenzene, 1-amino-3,4-methylenedioxybenzene and 1- (2'-hydroxyethyl) -amino 3,4-methylenedioxybenzene and their physiologically
  • coupler components according to the invention are 1-naphthol, 1, 5, 2,7- and 1, 7-dihydroxynaphthalene, 3-aminophenol, 5-amino-2-methylphenol, 2-amino-3-hydroxypyridine, resorcinol, 4-chlororesorcinol , 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol and 2,6-dihydroxy-3,4-dimethylpyridine and the physiologically acceptable salts of the aforementioned compounds.
  • the agents preferably contain the developer components in an amount of 0.005 to 10% by weight, preferably from 0.1 to 5% by weight, in each case based on the total agent.
  • the agents contain the coupler components preferably in an amount of 0.005 to 10 wt .-%, preferably from 0.1 to 5 wt .-%, each based on the total agent.
  • the agent can be used as color-modifying component in the form of Oxofarbstoffvor pasus at least one combination of at least one compound of the component
  • Compounds according to the invention having a reactive carbonyl group (also referred to below as reactive carbonyl compounds or component A) have at least one carbonyl group as reactive group which reacts with the compounds of component B to form a chemical bond linking both components. Furthermore, those compounds according to the invention are also included as component A in which the reactive carbonyl group is derivatized or masked in such a way that the reactivity of the carbon atom of the derivatized or masked carbonyl group with respect to component B is always present.
  • These derivatives are preferably condensation compounds of reactive carbonyl compounds with a) amines and their derivatives to form imines or oximes as a condensation compound b) alcohols to form acetals or ketals as a condensation compound c) water to form hydrates as a condensation compound of aldehydes.
  • Component A is preferably selected from the group formed from acetophenone, propiophenone, 2-hydroxyacetophenone, 3-hydroxyacetophenone, 4-hydroxyacetophenone, 2-hydroxypropiophenone, 3-hydroxypropiophenone, 4-hydroxypropiophenone, 2-hydroxybutyrophenone, 3 Hydroxybutyrophenone, 4-hydroxybutyrophenone, 2,4-dihydroxyacetophenone, 2,5-dihydroxyacetophenone, 2,6-dihydroxyacetophenone, 2,3,4-trihydroxyacetophenone, 3,4,5-trihydroxyacetophenone, 2,4,6-dihydroxyacetophenone Trihydroxyacetophenone, 2,4,6-trimethoxyacetophenone, 3,4,5-trimethoxyacetophenone, 3,4,5-trimethoxyacetophenone diethyl ketal, A-hydroxy-3-methoxy-acetophenone, 3,5-dimethoxy-4- hydroxyacetophenone, 4-aminoacetophenone, 4-dimethylamin
  • CH-acidic compounds are generally considered to carry a bound to an aliphatic carbon atom hydrogen atom, wherein due to electron-withdrawing substituents activation of the corresponding carbon atom Hydrogen bond is effected.
  • CH-acidic compounds also include enamines which are formed by alkaline treatment of quaternized N-heterocycles with a CH-acidic alkyl group in conjugation with the quaternary nitrogen.
  • the CH-acidic compounds of component B are preferably selected from the group consisting of 1, 2,3,3-tetramethyl-3H-indolium iodide, 1, 2,3,3-tetramethyl-3H-indolium p-toluenesulfonate, 1, 2,3,3-tetramethyl-3H-indolium methanesulfonate, 1,3,3-trimethyl-2-methylenindoline (Fischer's base), 2,3-dimethylbenzothiazolium iodide, 2,3-dimethylbenzothiazolium p-toluenesulfonate, 2,3-dimethyl-naphtho [1,2-d] thiazolium p-toluenesulfonate, 3-ethyl-2-methylnaphtho [1,2-d] thiazolium p-toluenesulfonate, rhodanine, rhodanine-3-acetic acid
  • Preferred primary or secondary aromatic amines of component B are selected from N, N-dimethyl-p-phenylenediamine, N, N-diethyl-p-phenylenediamine, N- (2-hydroxyethyl) -N-ethyl-p-phenylenediamine, N, N-bis (2-hydroxyethyl) -p-phenylenediamine, N- (2-methoxyethyl) -p-phenylenediamine, 2,3-dichloro-p-phenylenediamine, 2,4-dichloro-p-phenylenediamine, 2.5- Dichloro-p-phenylenediamine, 2-chloro-p-phenylenediamine, 2,5-dihydroxy-4-morpholinoaniline, 2-aminophenol, 3-aminophenol, 4-aminophenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4- aminophenol, o-phenylenediamine, m-phen
  • R 7 represents a hydroxy or an amino group represented by C
  • R 8 , R 9 , R 10 , R 11 and R 12 independently of one another represent a hydrogen atom, a hydroxy or an amino group which is represented by C 1 -C 4 -alkyl-, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 - Alkoxy, Ci-C 4 - Aminoalkyl- or Ci-C 4- Alkoxy-Ci-C 4 -alkyl phenomenon can be substituted, stand, and
  • P is a direct bond, a saturated or unsaturated, optionally substituted by hydroxy groups carbon chain having 1 to 4 carbon atoms, a carbonyl, sulfoxy, sulfonyl or imino group, an oxygen or sulfur atom, or a group having the formula IM
  • Q signifies a direct bond, a CH 2 or CHOH group
  • Q 'and Q "independently represent an oxygen atom, an NR 13 group, wherein R 13 is a hydrogen atom, a Ci_ 4 alkyl or a it being possible for both groups together with the remainder of the molecule to form a 5-, 6- or 7-membered ring, the group O- (CH 2 ) p -NH or NH- (CH 2 ) p -O, where p and p ' 2 or 3 are, stand and
  • O is a number from 1 to 4, such as 4,4'-diaminostilbene and its hydrochloride, 4,4'-diaminostilbene-2,2'-disulphonic acid mono- or di-Na salt, 4-amino-4'-dimethylaminostilbene and its hydrochloride, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylsulfide, 4,4'-diaminodiphenylsulfoxide, 4,4'-diaminodiphenylamine, 4,4'-diaminodiphenylamine-2-sulfonic acid, 4,4'-diaminobenzophenone, 4,4 ' - Diaminodiphenylether, 3,3 ', 4,4'-tetraaminodiphenyl, 3,3', 4,4'-tetraamino-benzophenone, 1, 3-bis (2,4-diaminophenoxy) -
  • the abovementioned compounds can be used both in free form and in the form of their physiologically acceptable salts, in particular as salts of inorganic acids, such as hydrochloric or sulfuric acid.
  • Suitable nitrogen-containing heterocyclic compounds are, for. B. 2-aminopyridine, 3-aminopyridine, 4-aminopyridine, 2-amino-3-hydroxy-pyridine, 2,6-diamino-pyridine, 2,5-diamino-pyridine, 2- (aminoethylamino) -5-aminopyridine, 2,3-diamino-pyridine, 2-dimethylamino-5-amino-pyridine, 2-methylamino-3-amino-6-methoxy-pyridine, 2,3-diamino-6-methoxy-pyridine, 2,6-dimethoxy 3,5-diamino-pyridine, 2,4,5-triamino-pyridine, 2,6-dihydroxy-3,4-dimethyl-pyridine, N- [2- (2,4-diaminophenyl) aminoethyl] -N- (5- amino-2-pyridyl) amine, N- [2- (4-aminopheny
  • heterocyclic compounds according to the invention can be used in DE-U1-299 08 573 disclosed hydroxypyrimidines.
  • the aforementioned compounds can be used both in free form and in the form of their physiologically acceptable salts, for. B. as salts of inorganic acids, such as hydrochloric or sulfuric acid, are used.
  • Suitable aromatic hydroxy compounds are, for.
  • the compounds of component A and the compounds of component B are preferably used in the compositions in each case in an amount of 0.03 to 65 mmol, in particular from 1 to 40 mmol, based on 100 g of the total Nuancierstoffs used.
  • the molar ratio of the compound of component A and the compound of component B may range from 0.5 to 2.0, preferably using equimolar amounts.
  • the actual Nuancierstoff is prepared with separate storage of components A and B immediately before use by mixing.
  • indoles and indolines which have at least one hydroxy or amino group, preferably as a substituent on the six-membered ring.
  • these groups may carry further substituents, e.g. Example in the form of etherification or esterification of the hydroxy group or alkylation of the amino group.
  • the colorants contain at least one indole and / or indoline derivative.
  • Particularly suitable precursors of naturally-analogous hair dyes are derivatives of 5,6-dihydroxyindoline of the formula (IVa),
  • R 1 is hydrogen, a C 1 -C 4 -alkyl group or a C 1 -C 4 -hydroxy-alkyl group
  • R 2 is hydrogen or a -COOH group, wherein the -COOH group may also be present as a salt with a physiologically compatible cation
  • R 3 is hydrogen or a C 1 -C 4 alkyl group
  • R 4 is hydrogen, a dC ⁇ alkyl group or a group -CO-R 6 , in which R 6 is a C-rC 4 alkyl group, and
  • R 5 is one of the groups mentioned under R 4 , as well as physiologically acceptable salts of these compounds with an organic or inorganic acid.
  • indoline Particularly preferred derivatives of indoline are 5,6-dihydroxyindoline, N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline,
  • N-methyl-5,6-dihydroxyindoline N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline and especially 5, 6-Dihydroxyindolin.
  • R 1 is hydrogen, a C 1 -C 4 -alkyl group or a C 1 -C 4 -hydroxyalkyl group
  • R 2 is hydrogen or a -COOH group, wherein the -COOH group may also be present as a salt with a physiologically compatible cation,
  • R 3 is hydrogen or a C 1 -C 4 alkyl group
  • R 4 is hydrogen, a C 1 -C 4 alkyl group or a group -CO-R 6 , in which R 6 is a C 1 -C 4 alkyl group, and
  • R 5 is one of the groups mentioned under R 4 , as well as physiologically acceptable salts of these compounds with an organic or inorganic acid.
  • Particularly preferred derivatives of indole are 5,6-dihydroxyindole, N-methyl-5,6-dihydroxyindole, N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6- dihydroxyindole, 5,6-dihydroxyindole-2-carboxylic acid, 6-hydroxyindole, 6-aminoindole and 4-aminoindole.
  • N-methyl-5,6-dihydroxyindole N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6-dihydroxyindole, and especially the 5,6 -Dihydroxyindol.
  • Preferred substantive dyes which find use as color-modifying components in the compositions are nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
  • Preferred substantive dyes are those having the international designations or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, Acid Yellow 1, Acid Yellow 10, Acid Yellow 23, Acid Yellow 36, HC Orange Disperse Orange 3, Acid Orange 7, HC Red 1, HC Red 3, HC Red 10, HC Red 11, HC Red 13, Acid Red 33, Acid Red 52, HC Red BN, Pigment Red 57: 1, HC Blue 2, HC Blue 12, Disperse Blue 3, Acid Blue 7, Acid Green 50, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Acid Violet 43, Disperse Black 9, Acid Black 1, and Acid Black 52 known compounds as well as 1 , 4-diamino-2-nitrobenzene, 2-amino-4-nitrophenol, 1, 4-bis ( ⁇ -hydroxyethyl) amino-2-nitrobenzen
  • the agents may contain a cationic substantive dye. Particularly preferred are
  • aromatic systems substituted with a quaternary nitrogen group such as Basic Yellow 57, Basic Red 76, Basic Blue 99, Basic Brown 16 and Basic Brown 17, as well as
  • Preferred cationic substantive dyes of group (c) are in particular the following compounds:
  • the compounds of the formulas (DZ1), (DZ3) and (DZ5) which are also known by the names Basic Yellow 87, Basic Orange 31 and Basic Red 51, are very particularly preferred cationic substantive dyes of group (c).
  • the cationic substantive dyes sold under the trademark Arianor are also very particularly preferred cationic substantive dyes according to the invention.
  • the agents contain the substantive dyes preferably in an amount of 0.01 to 20 wt .-%, based on the ready-to-use agent.
  • preparations may also naturally occurring dyes such as henna red, henna neutral, henna black, chamomile flower, sandalwood, black tea, buckthorn bark, sage, bluewood, madder root, Catechu, Sedre and alkano root are included.
  • naturally occurring dyes such as henna red, henna neutral, henna black, chamomile flower, sandalwood, black tea, buckthorn bark, sage, bluewood, madder root, Catechu, Sedre and alkano root are included.
  • oxidation dye precursors or the direct dyes it is not necessary for the oxidation dye precursors or the direct dyes to be in each case homogeneous compounds. Rather, in the compositions, due to the production process for the individual dyes, minor amounts of other components may be included, as far as they do not adversely affect the dyeing result or for other reasons, e.g. toxicological, must be excluded.
  • a further embodiment of the composition is a hair dye which is mixed immediately before use of two components, wherein the first component comprises an agent containing in a carrier at least one developer component and optionally at least one
  • the second component is an oxidizing agent composition containing at least one chemical oxidizing agent, in particular hydrogen peroxide, and at least one of the two components contains at least one compound according to formula (I),
  • R 1 , R 2 and R 3 independently of one another represent a C 1 - to C 4 -alkyl group or a C 2 - to C 4 -
  • R 4 is a hydrogen atom, a C 1 - to C 4 -alkyl group or a C 2 - to C 6 -
  • R 5 is a hydrogen atom, a negative charge or a C 1 - to C 4 alkyl group.
  • the first component contains at least one compound of the formula (I).
  • an oxidative dyeing can be carried out in the presence of atmospheric oxygen in the presence of oxidation dye precursors.
  • a chemical oxidizing agent also called oxidizing agent
  • oxidizing agent is used, especially if, in addition to the coloring, a whitening effect of the natural pigments of the human hair is desired. This lightening effect may be desired regardless of the staining method.
  • the presence of oxidation dye precursors is not a mandatory requirement for the use of oxidizing agents in the cosmetic compositions of the process according to the invention.
  • a chemical oxidizing agent is in particular hydrogen peroxide and / or at least one addition product thereof, in particular to inorganic or organic compounds such as sodium perborate, sodium percarbonate, magnesium percarbonate,
  • n H 2 O 2 a positive integer greater than 0
  • urea peroxide and melamine peroxide in question.
  • the actual colorant is prepared by separate storage of the dye precursors and the chemical oxidant immediately before use by mixing.
  • the agent before the application of a composition comprising in a cosmetic carrier at least one color changing component, and a further composition containing in a cosmetic carrier at least one oxidizing agent, mixed.
  • the actual (oxidative) hair dye is conveniently prepared immediately prior to use by mixing a separate oxidizer composition with the composition containing the color-changing components, preferably in the weight ratio range of 1 to 4 to 4 to 1, especially 1 to 2 to 2 to 1.
  • the colorant can also be applied to the hair together with a catalyst which activates the oxidation of the dye precursors, for example by atmospheric oxygen.
  • catalysts are, for example, metal ions, iodides, quinones or certain enzymes.
  • the catalysts can also be used in the presence of an oxidizing agent.
  • Suitable metal ions are, for example, Zn 2+ , Cu 2+ , Fe 2+ , Fe 3+ , Mn 2+ , Mn 4+ , Li + , Mg 2+ , Ca 2+ and Al 3+ . Particularly suitable are Zn 2+ , Cu 2+ and Mn 2+ .
  • the metal ions can in principle be used in the form of any physiologically acceptable salt or in the form of a complex compound.
  • Preferred salts are the acetates, sulfates, halides, lactates and tartrates.
  • Suitable enzymes are e.g. Peroxidases that can significantly increase the effect of small amounts of hydrogen peroxide. Furthermore, such enzymes are suitable according to the invention which directly oxidize the oxidation dye precursors with the aid of atmospheric oxygen, such as, for example, the laccases, or generate small amounts of hydrogen peroxide in situ and thus biocatalytically activate the oxidation of the dye precursors. Particularly suitable catalysts for the oxidation of the dye precursors are the so-called 2-electron oxidoreductases in combination with the specific substrates, e.g.
  • Lactate oxidase and lactic acid and their salts Lactate oxidase and lactic acid and their salts
  • the ready-to-use composition is conveniently prepared immediately prior to use by mixing a composition containing the oxidizing agent with the composition containing the color-changing components.
  • the resulting ready-to-use hair dye preparation should preferably have a pH in the range of 6 to 12. Particularly preferred is the use of the colorants in a weakly alkaline medium.
  • Another embodiment of the composition is a hair bleach which is mixed immediately prior to use of two components, wherein the first component comprises an agent containing in a carrier at least one alkalizing agent and optionally at least one bleach booster, the second component an oxidizing agent composition containing at least one chemical Oxidizing agent, in particular hydrogen peroxide, and at least one of the two components contains at least one compound according to formula (I),
  • R 1, R 2 and R 3 independently represent a C to C 4 alkyl group or a C 2 - to C 4 -
  • R 4 is a hydrogen atom, a C 1 - to C 4 -alkyl group or a C 2 - to C 6 -
  • R 5 is a hydrogen atom, a negative charge or a C 1 to C 4 alkyl group.
  • At least one bleach booster is additionally preferably used in addition to the chemical oxidizing agents.
  • Bleach boosters are preferably used in bleaching agents for increasing the bleaching action of the chemical oxidizing agent, in particular the hydrogen peroxide.
  • bleach amplifiers it is possible to use compounds which, under perhydrolysis conditions, give aliphatic peroxycarboxylic acids having preferably 1 to 10 C atoms, in particular 2 to 4 C atoms, and / or optionally substituted perbenzoic acid.
  • Suitable substances are those which carry O- and / or N-acyl groups of the stated C atom number and / or optionally substituted benzoyl groups.
  • polyacylated alkylene diamines in particular tetraacetylethylenediamine (TAED), acylated triazine derivatives, in particular 1,5-diacetyl-2,4-dioxohexahydro-1,3,5-triazine (DADHT), acylated glycolurils, especially tetraacetylglycoluril (TAGU), N-acylimides, in particular N-nonanoylsuccinimide (NOSI), acylated phenolsulfonates, in particular n-nonanoyl or isononanoyloxybenzenesulfonate (n- or iso- NOBS), carboxylic acid anhydrides, in particular phthalic anhydride, acylated polyhydric alcohols, in particular triacetin, ethylene glycol diacetate and 2,5-diacetoxy-2,5-dihydrofuran.
  • TAED tetraacetyl
  • Bleach amplifiers are preferably peroxo compounds.
  • the bleach-enhancing peroxy compounds according to the invention there are no addition products of hydrogen peroxide to other components and also not hydrogen peroxide itself.
  • the choice of peroxo compounds is subject to no restrictions.
  • Preferred peroxo compounds are peroxydisulfate salts, monopersulfate salts, (especially ammonium peroxydisulfate, potassium peroxodisulfate, sodium peroxodisulfate, ammonium monopersulfate, potassium monopersulfate, sodium monopersulfate, potassium peroxydiphosphate) and peroxides (such as barium peroxide, calcium peroxide and magnesium peroxide).
  • the inorganic compounds are preferred according to the invention. Particularly preferred are the peroxydisulfates, in particular ammonium peroxydisulfate.
  • the bleach boosters are contained in the ready-to-use compositions preferably in amounts of 5-30% by weight, in particular in amounts of 8-20% by weight.
  • the cosmetic compositions when acting as a bleaching agent, contain as preferred alkalizing agent at least one compound selected from ammonia, ammonium, alkali metal and alkaline earth metal hydroxides, carbonates, bicarbonates, hydroxycarbonates, metasilicates and carbamides, and alkali phosphates Alkanolamines such as 2-ethanolamine.
  • the ready-to-use agent may have a nonphysiological pH in the embodiment as a coloring or bleaching agent. It should preferably have a pH in the range of pH 7.5 to pH 12, in particular from pH 7.5 to pH 11.
  • the agents may additionally contain all known and commonly used active ingredients and auxiliaries in these fields.
  • the agents additionally contain at least one surfactant, with both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants being suitable in principle. In many cases, however, it has proved to be advantageous to select the surfactants from anionic, zwitterionic or nonionic surfactants.
  • Suitable anionic surfactants in preparations are all anionic surfactants suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such. Example, a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group having about 10 to 22 carbon atoms.
  • glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups may be present in the molecule.
  • suitable anionic surfactants are, in each case in the form of the sodium, potassium and ammonium and the mono-, di- and Trialkanolammoniumsalze with 2 or 3 C atoms in the alkanol group, linear fatty acids having 10 to 22 carbon atoms (soaps ), anionic alkyl oligoglycosides or anionic alkenyl oligoglycoside derivatives selected from alkyl and / or alkenyl oligoglycoside carboxylates, sulfates, phosphates and / or isethionates, which are derived from alkyl and / or alkenyl oligoglycosides of the general formula (V), RO- (G) p (V) with the meaning
  • G glycoside unit which is derived from a sugar containing 5 or 6 carbon atoms, p number from 1 to 10, in particular the Laurylglucosidcarboxylat, such as is available as Plantapon ® LGC from Cognis Germany.
  • esters of tartaric acid and citric acid with alcohols the addition products of about
  • Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids having 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule and in particular salts of saturated and in particular unsaturated C 8 -C 22 carboxylic acids, such as oleic acid, stearic acid, isostearic acid and palmitic acid.
  • Nonionic surfactants contain as hydrophilic group z.
  • Such compounds are, for example
  • Alkylphenols having 8 to 15 C atoms in the alkyl group having 8 to 15 C atoms in the alkyl group
  • Preferred nonionic surfactants are alkyl polyglycosides of the general formula R 1 O- (Z) x . These connections are identified by the following parameters.
  • the alkyl radical R 1 contains 6 to 22 carbon atoms and may be both linear and branched. Preference is given to primary linear and methyl-branched in the 2-position aliphatic radicals.
  • Such alkyl radicals are, for example, 1-octyl, 1-decyl, 1-lauryl, 1-myristyl, 1-cetyl and 1-stearyl. Particularly preferred are 1-octyl, 1-decyl, 1-lauryl, 1-myristyl.
  • oxo-alcohols compounds with an odd number of carbon atoms in the alkyl chain predominate.
  • the alkyl polyglycosides which can be used according to the invention can contain, for example, only one particular alkyl radical R 1 .
  • these compounds are starting made from natural fats and oils or mineral oils.
  • the alkyl radicals R are mixtures corresponding to the starting compounds or corresponding to the particular work-up of these compounds.
  • R 1 consists essentially of C 8 and C 10 -alkyl groups, essentially of C 2 - and C 4 -alkyl groups, essentially of C 8 - to C-
  • sugar building block Z it is possible to use any desired mono- or oligosaccharides.
  • sugars with 5 or 6 carbon atoms and the corresponding oligosaccharides are used.
  • Such sugars are, for example, glucose, fructose, galactose, arabinose, ribose, xylose, lyxose, allose, altrose, mannose, gulose, idose, talose and sucrose.
  • Preferred sugar building blocks are glucose, fructose, galactose, arabinose and sucrose; Glucose is particularly preferred.
  • alkyl polyglycosides which can be used according to the invention contain on average from 1.1 to 5 sugar units. Alkyl polyglycosides having x values of 1.1 to 1.6 are preferred. Very particular preference is given to alkyl glycosides in which x is 1: 1 to 1, 4.
  • the alkyl glycosides can also serve to improve the fixation of fragrance components on the hair.
  • This substance class as a further ingredient of the preparations in the event that an effect of the perfume oil on the hair that goes beyond the duration of the hair treatment is desired.
  • alkoxylated homologs of said alkyl polyglycosides can also be used according to the invention. These homologs may contain on average up to 10 ethylene oxide and / or propylene oxide units per alkyl glycoside unit.
  • zwitterionic surfactants can be used, in particular as cosurfactants.
  • Zwitterionic surfactants are surface-active compounds which carry at least one quaternary ammonium group and at least one -COO () or -SO 3 ' " ' group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as N-alkyl-N , N-dimethylammonium glycinates, for example the cocoalkyl di- methylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example cocoacylaminopropyl-dimethylammonium glycinate, and 2-alkyl-3-carboxylmethyl-3-hydroxyethyl-imidazoline having in each case 8 to 18 C atoms in the alkyl or acyl group and the coco acylaminoethylhydroxyethylcarboxymethylglycinate.
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known by the INCI name Cocamidopropyl Betaine.
  • ampholytic surfactants are to be understood as meaning those surface-active compounds which, apart from a C 8 -C 20 -alkyl or acyl group in the molecule, contain at least one free amino group and at least one -COOH or -SO 3 H group and which are capable of forming internal salts .
  • suitable ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each having about 8 to 18 C atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, coco
  • the cationic surfactants used are, in particular, those of the quaternary ammonium compound type, the esterquats and the amidoamines.
  • Preferred quaternary ammonium compounds are ammonium halides, especially chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, e.g.
  • alkyltrimethylammonium chlorides dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, e.g.
  • cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride as well as the imidazolium compounds known under the INCI names Quaternium-27 and Quaternium-83.
  • the long alkyl chains of the above-mentioned surfactants preferably have 10 to 18 carbon atoms.
  • Esterquats are known substances which contain both at least one ester function and at least one quaternary ammonium group as a structural element.
  • Preferred esterquats are quaternized ester salts of fatty acids with triethanolamine, quaternized ester salts of fatty acids with diethanolalkylamines and quaternized ester salts of fatty acids with 1,2-dihydroxypropyldialkylamines.
  • Such products are marketed under the trade names Stepantex® ®, ® and Dehyquart® Armocare® ®.
  • the alkylamidoamines are usually prepared by amidation of natural or synthetic fatty acids and fatty acid cuts with dialkylaminoamines.
  • An inventively particularly suitable compound from this group of substances under the name Tegoamid ® S 18 commercial stearamidopropyl dimethylamine is.
  • cationic surfactants which can be used according to the invention are the quaternized protein hydrolysates.
  • cationic silicone oils such as, for example, the commercially available products Q2-7224 (manufacturer: Dow Corning, a stabilized trimethylsilylamodimethicone), Dow Corning 929 emulsion (containing a hydroxylamino-modified silicone, also referred to as amodimethicones), SM -2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abif-Quat 3270 and 3272 (manufacturer: Th. Goldschmidt; diquaternary polydimethylsiloxanes, quaternium-80).
  • Glucquat ® 100 is, according to INCI nomenclature a "lauryl methyl Gluceth-10 Hydroxypropyl Dimonium Chloride”.
  • the compounds used as surfactant with alkyl groups may each be uniform substances. However, it is generally preferred to use native vegetable or animal raw materials in the production of these substances, so that substance mixtures having different alkyl chain lengths depending on the respective raw material are obtained.
  • both products with a "normal” homolog distribution and those with a narrow homolog distribution can be used.
  • "normal” homolog distribution are meant mixtures of homologs obtained in the reaction of fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alcoholates as catalysts. Narrowed homolog distributions are obtained when, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or Alcohols are used as catalysts.
  • the use of products with narrow homolog distribution may be preferred.
  • agents may contain further active ingredients, auxiliaries and additives, for example nonionic polymers, for example vinylpyrrolidone / vinyl acrylate copolymers,
  • dimethyldiallylammonium chloride polymers acrylamide-dimethyldiallylammonium chloride copolymers, diethyl sulfate quaternized dimethylaminoethylmethacrylate-vinylpyrrolidone copolymers, vinylpyrrolidone-imidazolinium methochloride copolymers and quaternized polyvinyl alcohol, zwitterionic and amphoteric polymers such as acrylamidopropyltrimidine methylammonium chloride / acrylate copolymers and octylacrylamide / methyl methacrylate / tert-butyl
  • Butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers anionic polymers such as polyacrylic acids, crosslinked polyacrylic acids,
  • Structural agents such as maleic acid and lactic acid, hair conditioning compounds such as phospholipids, for example soya lecithin, egg lecithin and cephalins,
  • Protein hydrolysates in particular elastin, collagen, keratin, milk protein, soy protein and
  • Solvents and mediators such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol, fiber structure-improving agents, in particular mono-, di- and oligosaccharides such as glucose, galactose, fructose, fructose and lactose, quaternized amines such as methyl-1-alkylamidoethyl -2-alkylimidazolinium methosulfate
  • Anti-dandruff agents such as Piroctone Olamine, Zinc Omadine and Climbazole,
  • Light stabilizers in particular derivatized benzophenones, cinnamic acid derivatives and
  • Active ingredients such as allantoin, pyrrolidonecarboxylic acids and their salts, and also bisabolol, vitamins, provitamins and vitamin precursors, in particular those of groups A, B 3 , B 5 , B 6 , C, E, F and H,
  • Plant extracts such as extracts of green tea, oak bark, stinging nettle, witch hazel, hops, chamomile, burdock root, horsetail, hawthorn, lime blossom, almond, aloe vera, spruce needle, horse chestnut, sandalwood, juniper, coconut, mango, apricot, lime, wheat, kiwi , Melon, orange, grapefruit, sage, rosemary, birch, mallow, meadowfoam, quenelle, yarrow, thyme, lemon balm, toadstool, coltsfoot, marshmallow, meristem, ginseng and ginger root ,. Cholesterol,
  • Bodying agents such as sugar esters, polyol esters or polyol alkyl ethers, fats and waxes such as spermaceti, beeswax, montan wax and paraffins, fatty acid alkanolamides,
  • Complexing agents such as EDTA, NTA, ⁇ -alaninediacetic acid and phosphonic acids, swelling and penetrating agents such as glycerol, propylene glycol monoethyl ether, carbonates, bicarbonates, guanidines, ureas and primary, secondary and tertiary phosphates, opacifiers such as latex, styrene / PVP and styrene / acrylamide copolymers Pearlescing agents such as ethylene glycol mono- and distearate and PEG-3-distearate, pigments,
  • Stabilizers for hydrogen peroxide and other oxidizing agents propellants such as propane-butane mixtures, N 2 O, dimethyl ether, CO 2 and air, antioxidants.
  • the agent contains the ingredients according to the invention in a cosmetic carrier.
  • a cosmetic carrier are, for example, creams, emulsions, gels or surfactant-containing foaming solutions, such as shampoos, foam aerosols or other preparations which are particularly suitable for use on the hair.
  • the ingredients in a powdered or tablet-like formulation, which is dissolved in water before use.
  • the carriers may in particular be aqueous or aqueous-alcoholic.
  • An aqueous carrier contains at least 50% by weight of water.
  • aqueous-alcoholic carriers are to be understood as meaning aqueous solutions containing from 3 to 70% by weight of a C 1 -C 4 -alcohol, in particular ethanol or isopropanol.
  • the compositions according to the invention may additionally contain further organic solvents, for example methoxybutanol, benzyl alcohol, ethyl diglycol or 1,2-propylene glycol. Preference is given to all water-soluble organic solvents.
  • a fourth object of the present invention is a cosmetic method for hair treatment in which an agent according to the third subject of the invention is applied to hair and the hair roots bearing skin parts and rinsed again after an exposure time.
  • the application temperatures can be in a range between 15 and 40 0 C.
  • the agent is removed by rinsing off the hair.
  • the washing with a shampoo is omitted if a strong surfactant-containing carrier, such as a shampoo was used.
  • a fifth item is a cosmetic procedure in which
  • R 1 , R 2 and R 3 independently of one another are a C 1 to C 4 alkyl group or a C 2 to C 4 hydroxyalkyl group
  • R 4 is a hydrogen atom, a C 1 to C 4 alkyl group or a C 2 - to C 6 acyl group
  • R 5 is a hydrogen atom, a negative charge or a C 1 - to C 4 -Al gylg group, and rinsed again after an exposure time.
  • a "treatment" according to the first step is preferably carried out by application of a corresponding cosmetic composition After a period of action has elapsed, the cosmetic composition is rinsed out again.
  • hair colorants or hair bleaches which contain at least one chemical oxidizing agent and / or at least one color-modifying component in a cosmetic carrier are used as hair treatment compositions of the first step.
  • the application temperatures for both steps may be in a range between 15 and 40 ° C.
  • the agent is removed by rinsing off the hair.
  • the washing with a shampoo is omitted if a strong surfactant-containing carrier, such as a shampoo was used.
  • the agent can thus be provided in a packaging unit (kit) which contains at least one separately prepared inventive agent of the fifth subject of the invention.
  • kit contains at least one separately prepared inventive agent of the fifth subject of the invention.
  • the kit may contain at least one separately formulated oxidizer composition, especially if an (oxidative) colorant is to be provided.
  • a sixth aspect of the invention is a kit comprising, in a container C1, a cosmetic composition which contains in a cosmetic carrier at least one compound of the formula (I), wherein
  • R 1 , R 2 and R 3 independently of one another are a C 1 - to C 4 -alkyl group or a C 2 - to
  • R 4 denotes a hydrogen atom, a C 1 - to C 4 -alkenyl group or a C 2 - to C 6 -acyl group,
  • R 5 is a hydrogen atom, a negative charge or a C 1 - to C 4 alkyl group, in a container C2, a cosmetic composition containing in a cosmetic carrier at least one cosmetic active ingredient.
  • the cosmetic active ingredient is preferably selected from chemical oxidizing agents and / or color-modifying components. Preferred representatives of these ingredients according to the invention were defined for the second or third subject of the invention.
  • composition of the container C2 contains as additional, cosmetic active ingredient at least one chemical oxidizing agent. It is again preferred if the cosmetic agent of the container C1 additionally contains at least one color-changing component which is selected.
  • kit may additionally contain optional instructions for use, application aids, mixing bowls or protective gloves.
  • the compositions of the kit may be mixed before application, or applied sequentially on the hair.
  • the above recipe was provided according to a known manufacturing method. Before use, the above formulation was mixed with an aqueous 6 wt .-% strength hydrogen peroxide lotion in a weight ratio of 1 to 1 and the mixture applied to the hair and rinsed out again after a contact time of 30 minutes.
  • the above recipe was provided according to a known manufacturing method. Before use, the above formulation was mixed with an aqueous 3 wt .-% hydrogen peroxide lotion in a weight ratio of 1 to 1 and the mixture applied to the hair and rinsed again after a contact time of 30 minutes.
  • hair follicles differ which were treated either with a placebo formulation (application mixture prepared according to example 2 without carnitine tartrate) or with an oxidative coloring with carnitine tartrate additive (application mixture prepared according to example 2).
  • a placebo formulation application mixture prepared according to example 2 without carnitine tartrate
  • an oxidative coloring with carnitine tartrate additive application mixture prepared according to example 2.
  • 21 subjects were treated over a period of 30 minutes on one half side with the placebo formulation and on the other half side with the formulation according to Example 2.
  • hair follicles were collected on each half side of each volunteer to obtain RNA.
  • apoptosis-relevant markers (Bax, Bcl-2, caspase 2, caspase 3, caspase 9, TNFalpha and cyclooxygenase 2) were analyzed by RNA using polymerase chain reaction (PCR).
  • the PCR provides information about the genetic information stored in the cell, ie the genes that are activated or deactivated by the treatment.
  • the investigations show that the addition of carnitine tartrate significantly reduces apoptosis in the treated hair follicles.
  • the quotient of the respective gene expression was formed and the two quotients (placebo / example 2) were compared.
  • the ratio of Bax and Bcl-2 is important because the pro-apoptotic (bax) and anti-apoptotic (Bcl-2) markers usually balance each other. If the equilibrium is influenced in favor of a marker, this can be said about apoptosis. If, for example, the ratio Bax / Bcl-2 decreases due to an increase in Bcl-2, this indicates increased apoptosis protection.
  • the total of 21 subjects were divided into 5 pools to reduce the number of samples.
  • Example 2 (according to the invention) ratio Bax / Bcl-2 ratio Bax / Bcl-2
  • the ratio between Bax and Bcl-2 could be influenced 15 hours after coloring.
  • the quotient of Bax and Bcl-2 is lower for all carnitine tartrate pools than for the no carnitine tartrate formulation. That is, apoptosis was reduced in terms of increased apoptosis protection in the hair follicle cells.
  • the values of the control treated with the placebo formulation were set to 1 and the change in expression in the follicles treated with the agent according to Example 2 was shown as an x-fold change).

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Abstract

La mort cellulaire programmée (apoptose) des cellules du follicule pileux est favorisée ou induite prématurément par des facteurs de stress, en particulier dans le cadre d'un traitement capillaire oxydant. L'utilisation de dérivés d'acide bêta-hydroxy-butyrique quaternisé protège les cheveux contre une apoptose prématurée des cellules folliculaires.
PCT/EP2007/059202 2006-09-06 2007-09-04 Diminution du vieillissement capillaire WO2008028895A1 (fr)

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Cited By (3)

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Publication number Priority date Publication date Assignee Title
DE102013219916A1 (de) 2013-10-01 2014-04-24 Henkel Ag & Co. Kgaa leistungsgesteigerte Haarbehandlungsmittel II
DE102013219920A1 (de) 2013-10-01 2015-04-02 Henkel Ag & Co. Kgaa leistungsgesteigerte Haarbehandlungsmittel
EP2879649B1 (fr) 2012-08-02 2018-11-07 L'oreal Composition de teinture comprenant au moins une substance grasse, au moins un agent oxydant et au moins un tensio-actif non ionique, anionique et amphotère

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WO2012119112A2 (fr) * 2011-03-03 2012-09-07 Toby Orthopaedics, Llc Dispositif de renfort cortical modulaire et non modulaire

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WO1998034610A1 (fr) * 1997-02-10 1998-08-13 Groton Robert B Composition favorisant la repousse des cheveux et son procede d'utilisation
WO2002074265A1 (fr) * 2001-03-19 2002-09-26 Hans Schwarzkopf Gmbh & Co. Kg Agent de soin capillaire comprenant des betaines
WO2004078117A2 (fr) * 2003-02-28 2004-09-16 E-L Management Corp. Methode visant a augmenter la croissance des cheveux
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EP1800654A2 (fr) * 2005-12-23 2007-06-27 Henkel Kommanditgesellschaft auf Aktien Réduction des signes de vieillesse des cheveux
EP1815839A2 (fr) * 2005-12-23 2007-08-08 Henkel KGaA Procédé de coloration des cheveux

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JPS51148042A (en) * 1975-06-14 1976-12-18 Kanebo Ltd Skin toiletry
WO1998034610A1 (fr) * 1997-02-10 1998-08-13 Groton Robert B Composition favorisant la repousse des cheveux et son procede d'utilisation
WO2002074265A1 (fr) * 2001-03-19 2002-09-26 Hans Schwarzkopf Gmbh & Co. Kg Agent de soin capillaire comprenant des betaines
WO2004078117A2 (fr) * 2003-02-28 2004-09-16 E-L Management Corp. Methode visant a augmenter la croissance des cheveux
WO2007003307A1 (fr) * 2005-07-05 2007-01-11 Henkel Kommanditgesellschaft Auf Aktien Agents contenant de la l-carnitine, des derives de l-carnitine et au moins une autre substance
EP1800654A2 (fr) * 2005-12-23 2007-06-27 Henkel Kommanditgesellschaft auf Aktien Réduction des signes de vieillesse des cheveux
EP1815839A2 (fr) * 2005-12-23 2007-08-08 Henkel KGaA Procédé de coloration des cheveux

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2879649B1 (fr) 2012-08-02 2018-11-07 L'oreal Composition de teinture comprenant au moins une substance grasse, au moins un agent oxydant et au moins un tensio-actif non ionique, anionique et amphotère
EP2879649B2 (fr) † 2012-08-02 2022-08-24 L'oreal Composition de teinture comprenant au moins une substance grasse, au moins un agent oxydant et au moins un tensio-actif non ionique, anionique et amphotère
DE102013219916A1 (de) 2013-10-01 2014-04-24 Henkel Ag & Co. Kgaa leistungsgesteigerte Haarbehandlungsmittel II
DE102013219920A1 (de) 2013-10-01 2015-04-02 Henkel Ag & Co. Kgaa leistungsgesteigerte Haarbehandlungsmittel
WO2015048945A1 (fr) 2013-10-01 2015-04-09 Henkel Ag & Co. Kgaa Agents de traitement capillaire à performances améliorées

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