WO2007115657A2 - Agents d'éclaircissement et/ou de coloration bien tolérés par la peau - Google Patents

Agents d'éclaircissement et/ou de coloration bien tolérés par la peau Download PDF

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WO2007115657A2
WO2007115657A2 PCT/EP2007/002527 EP2007002527W WO2007115657A2 WO 2007115657 A2 WO2007115657 A2 WO 2007115657A2 EP 2007002527 W EP2007002527 W EP 2007002527W WO 2007115657 A2 WO2007115657 A2 WO 2007115657A2
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acid
agents
amino
preferred
weight
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WO2007115657A3 (fr
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Horst Höffkes
Georg KNÜBEL
Claudia Brockmann
Denise Fuhr
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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    • 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
    • A61Q5/08—Preparations for bleaching the hair
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/23—Sulfur; Selenium; Tellurium; Compounds thereof
    • 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
    • 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
    • A61K8/41—Amines
    • 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
    • A61K8/42—Amides
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • 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
    • A61K8/55—Phosphorus compounds

Definitions

  • the invention relates to a blonding agent for human hair, in particular a bleaching agent for human hair, which is in paste or powder form.
  • solid or paste-like preparations with solid oxidizing agents are usually mixed with a dilute hydrogen peroxide solution immediately before use. This mixture is then applied to the hair and rinsed again after a certain exposure time.
  • the invention relates in a first embodiment to an agent for bleaching human hair, containing - in each case based on its weight - a) 5 to 70 wt .-% of at least one solid peroxo compound which is selected from ammonium and alkali metal persulfates and peroxydisulfates , b1) 0.05 to 5 wt .-% of at least one cyanate of the formula
  • M + [OCN] ' in which M + stands for K + , Na + , Li + or NH 4 + or Vz Ca 2+ , Vz Mg 2+ or Vz Zn 2+ and / or b2) 0.05 to 5% by wt .-% of at least one compound of the formula
  • the bleaching compositions according to the invention contain as the first compulsory component a solid peroxo compound which is selected from ammonium and alkali metal persulfates and peroxidisulfates.
  • a solid peroxo compound which is selected from ammonium and alkali metal persulfates and peroxidisulfates.
  • the selection of this peroxo compound is in principle not limited; Typical peroxo compounds known to the person skilled in the art are, for example, ammonium peroxydisulfate, potassium peroxodisulfate, sodium peroxodisulfate, ammonium persulfate, potassium persulfate, sodium persulfate.
  • the peroxydisulfates are preferred, in particular combinations of at least two peroxydisulfates.
  • Preferred agents according to the invention are therefore characterized in that they contain sodium peroxydisulfate and / or potassium peroxodisulfate and / or ammonium peroxodisulfate, preferred agents containing at least two different peroxidisulfates. Furthermore, use within narrower ranges is preferred, so that preferred agents according to the invention are characterized in that they contain from 6 to 65% by weight, preferably from 7.5 to 60% by weight, more preferably 8 to 55 wt .-% and in particular 10 to 50 wt .-% Peroxidisulfa.t (e) included.
  • the bleaching compositions according to the invention may contain an alkalizing agent which serves to adjust the alkaline pH of the application mixture. This is preferred according to the invention.
  • the usual alkalizing agents known to the person skilled in the art for bleaching agents such as ammonium, alkali metal and alkaline earth metal hydroxides, carbonates, bicarbonates, hydroxycarbonates, silicates, in particular metasilicates, and also alkali metal phosphates, can be used.
  • Short-chain amines such as monoethanolamines, 3-amino-2-methylpropanol or alkaline-reacting amino acids such as arginine, ornithine and lysine can also be used.
  • the bleaching powders according to the invention contain at least two different alkalizing agents. In this case, mixtures of, for example, a metasilicate and a hydroxycarbonate may be preferred.
  • the bleaching compositions according to the invention preferably comprise alkalizing agents in amounts of from 1 to 30% by weight, in particular from 2 to 25% by weight.
  • the bleaching agents according to the invention contain from 0.05 to 5% by weight of at least one cyanate of the formula M + [OCN] ' in M + for K + , Na + , Li + or NH 4 + or V-Ca 2 + , V ⁇ Mg 2+ or>. Zn 2+ and / or 0.05 to 5 wt .-% of at least one compound of the formula H 2 NC (O) -L, in which L is a displaceable by the anion " OOH group.
  • cyanates may be potassium cyanate, KOCN, and / or sodium cyanate, NaOCN, and / or lithium cyanate, LiOCN, and / or ammonium cyanate, NH 4 OCN, and / or calcium cyanate, Ca (OCN) 2 , and / or magnesium cyanate, Mg ( OCN) 2 , and / or zinc cyanate, Zn (OCN) 2 , are used.
  • Agents preferred according to the invention are characterized in that they contain 0.075 to 4% by weight, preferably 0.1 to 2.5% by weight and in particular 0.2 to 1% by weight of sodium cyanate and / or potassium cyanate and / or ammonium cyanate with sodium cyanate being particularly preferred.
  • H 2 NC (O) -L in which L is selected from -S-CH 2 -COOH 1 -S- (CH 2 ) 3 SO 3 H, -S- (CH 2 ) 2 -NH 2 , -OCH 3 , -O- (C 6 H 4 J-SO 3 M, -Q + , -NH-OH 1 -O-C (O) -R 1 , -O-C (O) -H 1 -O-CH (OH) 2 , -SO 3 M 1 -PH (O) OH 1 -P (O) (OH) 2 , - (NH-Glucosamine) n , -NH-C (O) -NH 2 , -NH-NH 2 , -NH-CN 1 -P (OH) (O) -C (O) NH 2 , -SCN 1 -OCN, -SC (NH) NH 2 , OONa
  • M is -H 1 Na, K, NH 4
  • Q is selected from quaternary ammonium radicals, heteroaryl radicals or non-aromatic heterocycles formed from tertiary amines and R 1 is --H, -CH 3 , -CH 2 CH 3 , - (CH 2 J 2 CH 3 , -CH (CH 3 J 2 or another alkyl group.
  • Particularly preferred agents according to the invention contain from 0.075 to 4% by weight, preferably from 0.1 to 3.5% by weight and in particular from 0.2 to 3% by weight of at least one of the compounds listed below:
  • the bleaching according to the invention contain nonionic surfactants.
  • Such surfactants having an HLB of 5.0 and greater are preferred.
  • HLB value For the definition of the HLB value, explicit reference is made to the statements in Hugo Janistyn, Handbuch der Kosmetika und Riechstoffe, III. Volume: The personal care products, 2nd edition, Dr. med. Alfred Hüthig Verlag Heidelberg, 1973, pages 68-78 and Hugo Janistyn, Paperback of modern perfumery and cosmetics, 4th edition, Scientific Publishing Company m.b.H. Stuttgart, 1974, pages 466-474, as well as the original works cited therein.
  • non-ionic surface-active substances are substances that are commercially available as solids or liquids in pure form because of their ease of processing.
  • the definition of purity in this context does not refer to chemically pure compounds. Rather, especially when it comes to natural-based products, mixtures of different homologs can be used, for example, with different alkyl chain lengths, such as those obtained with products based on natural fats and oils. Even with alkoxylated products, mixtures of different degrees of alkoxylation are usually present.
  • purity in this context refers rather to the fact that the chosen substances should preferably be free from solvents, stabilizers and other impurities.
  • Preferred nonionic surfactants are:
  • - alkoxylated fatty alcohols having 8 to 22, in particular 10 to 16, carbon atoms in the fatty alkyl group and 1 to 30, in particular 1 to 15, ethylene oxide and / or
  • Preferred fatty alkyl groups are, for example, lauryl, myristyl, cetyl, but also stearyl, isostearyl and oleyl groups.
  • Particularly preferred compounds of this class are, for example, lauryl alcohol with 2 to 4 ethylene oxide units, oleyl and cetyl alcohol with 5 to 10 ethylene oxide, cetyl alcohol and stearyl alcohol and mixtures thereof with 10 to 30 ethylene oxide units and the commercial product Aethoxal ® B (Henkel), a Lauryl alcohol with 5 ethylene oxide and 3 propylene oxide units.
  • alkoxylated fatty alcohols it is also possible to use so-called "end-capped” compounds according to the invention
  • the alkoxy group has no OH group at the end but is "closed” in the form of an ether, in particular a C 1 -C 4 -alkyl ether.
  • An example of such a compound is the commercially available product ® Dehypon LT 054, a C 12th 18- fatty alcohol + 4.5 ethylene oxide-butyl ether.
  • - alkoxylated fatty acids having 8 to 22, in particular 10 to 16, carbon atoms in the fatty acid group and 1 to 30, in particular 1 to 15, ethylene oxide and / or propylene oxide units.
  • Preferred fatty acids are, for example, lauric, myristic, palmitic, stearic, isostearic and oleic acids.
  • - alkoxylated, preferably propoxylated and especially ethoxylated, mono-, di- and triglycerides examples are glycerol monolaurate + 20 ethylene oxide and glycerol monostearate + 20 ethylene oxide.
  • Polyglycerol esters and alkoxylated polyglycerol esters are for example poly (3) glycerol diisostearate (commercial product: Lameform ® TGI (Henkel)) and poly (2) glycerinpolyhydroxy- stearate (commercial product: Dehymuls ® PGPH (Henkel)).
  • Sorbitan fatty acid esters and alkoxylated sorbitan fatty acid esters such as sorbitan monolaurate and sorbitan monolaurate + 20 ethylene oxide (EO).
  • Alkylphenols and Alkylphenolalkoxylate having 6 to 21, in particular 6 to 15, carbon atoms in the alkyl chain and 0 to 30 ethylene oxide and / or propylene oxide units.
  • Preferred representatives of this class are, for example, nonylphenol + 4 EO, nonylphenol + 9 EO, octylphenol + 3 EO and octylphenol + 8 EO.
  • nonionic surfactants are the alkoxylated fatty alcohols, the alkoxylated fatty acids and the alkylphenols and alkylphenol alkoxylates.
  • Agents according to the invention which contain non-ionic surface-active substances in amounts of 1 to 5% by weight have proved to be particularly advantageous.
  • the bleaching according to the invention may contain all known in such preparations active ingredients, additives and excipients.
  • the agents contain at least one surfactant, wherein in principle both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants are suitable.
  • anionic surfactants may be very particularly preferred.
  • Preferred anionic surfactants are alkyl sulfates, ether carboxylic acid salts having 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule such as C 12 H 25 - (C 2 H 4 O) 6 -CH 2 - COONa and in particular salts of saturated and especially unsaturated C8-C22 carboxylic acids such as oleic acid, stearic acid, isostearic acid and palmitic acid.
  • anionic surfactants should preferably be present in solid, in particular powder form. Very particular preference is given to solid soaps, especially sodium stearate, at room temperature. These are preferably present in amounts of from 5 to 20% by weight, in particular from 10 to 15% by weight.
  • Suitable nonionic surfactants are in particular C 8 -C 22 -alkyl mono- and oligoglycosides and their ethoxylated analogs.
  • the nonethoxylated compounds have been found to be particularly suitable.
  • cationic surfactants which can be used in the hair treatment compositions according to the invention are, in particular, quaternary ammonium compounds.
  • ammonium halides such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, eg. Cetyltrimethylammonium chloride,
  • Stearyltrimethylammonium chloride distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride.
  • Further cationic surfactants which can be used according to the invention are the quaternized protein hydrolysates.
  • Alkylamidoamines in particular fatty acid amidoamines, such as the stearylamidopropyldimethylamine obtainable under the name Tego Amid® S 18, are distinguished not only by a good conditioning action but also by their good biodegradability.
  • esterquats such as the Distearoylethylhydroxyethylammoniummethosulfat available in a blend with Cetearylalkohle under the name Dehyquart® ® F 75 miles.
  • the compounds containing alkyl groups used as surfactants may each be uniform substances. However, it is usually preferred to start with the production of these substances from native plant or animal raw materials, so that one Substance mixtures with different, depending on the particular raw material alkyl chain lengths obtained.
  • nonionic polymers such as vinyl pyrrolidone / vinyl acrylate copolymers, polyvinyl pyrrolidone and vinyl pyrrolidone / vinyl acetate copolymers and polysiloxanes, cationic polymers such as quaternized cellulose ethers, and other solid-stable compounds, zwitterionic and amphoteric polymers, which are stable or preferred as solids are available as commercial products, anionic polymers such as polyacrylic acids, crosslinked polyacrylic acids and vinyl acetate / crotonic acid copolymers, provided that they are stable or preferably commercially available as solids,
  • Thickeners such as agar-agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans, cellulose derivatives, e.g. For example, methylcellulose, hydroxyalkylcellulose and carboxymethylcellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such.
  • Bentonite or fully synthetic hydrocolloids such as e.g. Polyvinyl alcohol, structurants such as glucose, maleic acid and lactic acid, hair conditioning compounds such as phospholipids, for example soya lecithin, egg lecithin and cephalins, and silicone oils
  • Protein hydrolysates in particular elastin, collagen, keratin, milk protein, soy protein and wheat protein hydrolysates, their condensation products with fatty acids and quaternized protein hydrolysates, perfume oils, dimethyl isosorbide and cyclodextrins, dyes for coloring the preparations,
  • Active substances such as panthenol, pantothenic acid, allantoin, pyrrolidonecarboxylic acids and their salts,
  • Fats and waxes such as spermaceti, beeswax, montan wax, paraffins,
  • Complexing agents such as EDTA, NTA and phosphonic acids, Swelling and penetration substances such as carbonates, bicarbonates, guanidines. Ureas and primary, secondary and tertiary phosphates,
  • the agents according to the invention may contain one or more dye precursors.
  • compositions according to the invention which additionally comprise at least one oxidation-type dye precursor of the developer type and / or optionally at least one coupler-type oxidation dye precursor are preferred.
  • the present invention is not subject to any restrictions.
  • the bleaching agents according to the invention can be used as further dye precursors
  • Precursors of natural analog dyes such as indole and indoline derivatives, and mixtures of representatives of these groups.
  • the bleaching agent further contains at least one developer component.
  • developer components are usually primary aromatic amines with another, located in the para or ortho position, free or substituted hydroxy or amino group, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazole derivatives and 2,4,5,6-tetraaminopyrimidine and its derivatives used ,
  • p-phenylenediamine derivatives of the formula (E1) 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 (E1)
  • 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 J-AIkOXy- ( C 1 to C 4 ) alkyl, a 4'-aminophenyl or C 1 to C 4 alkyl substituted with a nitrogen-containing group, a phenyl or a 4'-aminophenyl;
  • G 2 is 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 (Ci to C 4 J-AIkOXy- (C 1 - to C 4) alkyl radical or a C 1 to 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 Ci to C 4 alkyl, 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 Ci to C 4 alkyl 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
  • 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 which are 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 (E1) are in particular the amino groups, C 1 - to C 4 -monoalkylamino groups, C 1 - to C 4 -dialkylamino groups, C 1 - to C 4 -trialkylammonium groups, C 1 - to C 4 - Monohydroxyalkylamino groups, imidazolinium and ammonium.
  • Particularly preferred p-phenylenediamines of the formula (E1) 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, N-bis-
  • Very particular preferred p-phenylenediamine derivatives of the formula (E1) 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 which 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 (E2) and their physiologically tolerated salts:
  • Z 1 and Z 2 independently of one another represent a hydroxyl or NH 2 -ReSt 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 bond 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 interrupted or terminated may be substituted by one or more hydroxyl or C r to C 8 -Al koxyreste, or a direct bond,
  • G 5 and G 6 are each independently a hydrogen or halogen atom, a Ci to C 4 alkyl radical, a Ci to C 4 monohydroxyalkyl radical, a C 2 - to C 4 -
  • Polyhydroxyalkyl radical a C 1 - to C 4 -Aminoalkylrest or a direct connection to
  • G 7 , G 8 , G 9 , G 10 , G 11 and G 12 independently of one another represent a hydrogen atom, a direct bond to the bridge Y or a C r to C 4 -alkyl radical, with the provisos that the compounds of the formula ( E2) contain only one bridging Y per molecule and the compounds of the formula (E2) contain at least one amino group which carries at least one hydrogen atom.
  • Preferred binuclear developer components of the formula (E2) 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 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-bis (2,5-diaminoph
  • Very particularly preferred binuclear developer components of the formula (E2) 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-amino-bis-1,3'-dibiaminophenyl O-1-A /.-O-tetraoxadecane or one of its physiologically acceptable salts.
  • p-aminophenol derivatives of the formula (E3) 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 (E3)
  • G 13 represents a hydrogen atom, a 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 , alkyl to C 4) a C 1 - -) alkoxy- (C 1 -C 4 aminoalkyl radical, a hydroxy ⁇ C ⁇ to C 4) - alkylamino, C 1 - to C 4 -Hydroxyalkoxyrest, a Ci- to d-hydroxyalkyl ⁇ d to C 4 ) aminoalkyl or a (di-C 1 - to C 4 alkylamino) - (C r to C 4 ) alkyl, and
  • G 14 represents a hydrogen or halogen 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 J- AIkOXy- (C 1 - to C 4 ) -alkyl radical, a C 1 - to C 4 -Aminoalkylrest 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.
  • Preferred p-aminophenols of the formula (E3) 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 (E3) are p-aminophenol, 4-amino-3-methylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- ( ⁇ , ⁇ -dihydroxyethyl) -phenol and 4-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 2,5-diamino-pyridine, 2- (4'-methoxyphenyl) amino-3-amino-pyridine, 2,3-diamino-6-methoxypyridine, 2- ( ⁇ -methoxyethyl ) amino-3-amino-6-methoxypyridine and 3,4-diamino-pyridine.
  • Preferred pyrimidine derivatives are in particular 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 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-methylpyrazole, 4,5-diamino-1 - tert-butyl-3-methylpyrazole, 4,5-diamino-1- ( ⁇ -hydroxyethyl) -3
  • Triaminopyrazole 1-methyl-3,4,5-triaminopyrazole, 3,5-diamino-1-methyl-4-methylaminopyrazole and 3, 5-diamino-4- ( ⁇ -hydroxyethyl) amino-1-methylpyrazole.
  • Preferred pyrazole-pyrimidine derivatives are, in particular, the derivatives of the pyrazolo [1,5-a] pyrimidine of the following formula (E4) 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 polyhydroxyalkyl a 4 J-AIkOXy- -C (C 1 - - C 4) - (C -)!
  • a C 1 - to C 4 - aminoalkyl radical which is optionally substituted by an acetyl ureide or a sulfonyl Rest can be protected, a (C 1 - to C 4 ) alkylamino (C 1 - to C 4 ) alkyl, a DK (C 1 - to C 4 ) alkyl] - (Cr to C 4 ) aminoalkyl where the dialkyl radicals optionally form a carbon cycle or a heterocycle having 5 or 6 chain members, a C 1 - to C 4 -hydroxyalkyl- or a di- (C 1 - to C 4 ) - [hydroxyalkyl] - (C 1 - to C 4 ) -aminoalkylrest, the X radicals 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 -hydroxy
  • the pyrazolo [1, 5-a] -pyrimidines of the above formula (E4) can be prepared as described in the literature by cyclization from an aminopyrazole or from hydrazine.
  • the agents according to the invention contain at least one coupler component.
  • coupler components m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenol derivatives are generally used.
  • Suitable coupler substances are in particular 1-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 1-phenyl 3-methyl-pyrazolone-5, 2,4-dichloro-3-aminophenol, 1, 3-bis (2 ', 4'-diaminophenoxy) -propane, 2- Chloro-resorcinol, 4-chloro-resorcinol, 2-chloro-6-methyl-3-aminophenol, 2-amino-3-hydroxypyridine, 2-methylresorcinol, 5-methylresorcinol and 2-methyl
  • Coupler components preferred according to the invention are m-aminophenol and its derivatives, such as, for example, 5-amino-2-methylphenol, N-
  • 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
  • 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
  • Morpholine derivatives such as 6-hydroxybenzomorpholine and 6-aminobenzomorpholine,
  • Indole derivatives such as 4-hydroxyindole, 6-hydroxyindole and 7-hydroxyindole,
  • Pyrimidine derivatives such as 4,6-diaminopyrimidine, 4-amino-2,6-dihydroxypyrimidine,
  • Amino-4-hydroxy-6-methylpyrimidine and 4,6-dihydroxy-2-methylpyrimidine or Methylenedioxybenzene derivatives such as 1-hydroxy-3,4-methylenedioxybenzene, 1-amino-3,4-methylenedioxybenzene and 1- (2'-hydroxyethyl) amino-3,4-methylenedioxybenzene.
  • 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.
  • 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 agents 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 (IIIa),
  • R 1 is hydrogen, a C 1 -C 4 -alkyl group or a C 1 -C 8 -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.
  • 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,
  • Particularly noteworthy within this group are 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 ⁇ 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.
  • the indoline and indole derivatives can be used in the agents used in the process according to the invention both as free bases and in the form of their physiologically acceptable salts with inorganic or organic acids, eg. As the hydrochlorides, the sulfates and Hydrobromide used.
  • the indole or indoline derivatives are contained therein usually in amounts of 0.05-10 wt .-%, preferably 0.2-5 wt .-%.
  • the amino acid is advantageously an ⁇ -amino acid; Very particularly preferred ⁇ -amino acids are arginine, ornithine, lysine, serine and histidine, in particular arginine.
  • Preferred agents according to the invention are characterized in that they contain at least one dye precursor from the groups of aromatic and heteroaromatic diamines, aminophenols, naphthols, polyphenols CH-acidic coupler components and their derivatives in amounts of from 0.01 to 25% by weight, preferably 0.5 to 10 wt.%, In particular from 1 to 5 wt .-%, each based on the total agent included.
  • compositions according to the invention for shading may contain one or more substantive dyes.
  • Direct dyes are usually 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 1, Disperse Orange 3, Acid Orange 7, HC Red 1, HC Red 3, HC Red 10, HC Red
  • Corresponding agents according to the invention which are characterized in that they contain at least one substantive dye from the group of cationic (basic) dyes, preferably Basic Blue 6, CI-No. 51, 175; Basic Blue 7, CI -No. 42.595; Basic Blue 9, Cl-No. 52.015; Basic Blue 26, Cl-No. 44.045; Basic Blue 41, Cl-No. 11, 154; Basic Blue 99, Cl-No. 56.059; Basic Brown 4, Cl-No. 21, 010; Basic Brown 16, Cl-No. 12.250; Basic Brown 17, Cl- No. 12,251; Basic Green 1, Cl-No. 42.040; Basic Orange 31; Basic Red 2, Cl-No. 50.240; Basic Red 22, Cl-No.
  • Basic Blue 6 cationic (basic) dyes
  • dyes some representatives are particularly preferred, for which reason further preferred agents according to the invention are characterized in that they comprise at least one direct-puller selected from Basic Blue 7, Basic Blue 99, Basic Violet 14, Basic Brown 16, Basic Brown 17, Basic Orange 31, Basic Red 46, Basic Red 51, Basic Red 76, Basic Yellow 57, Basic Yellow 87, Acid Black 1, Acid Blue 7, Acid Violet 43, Acid Red 23, Acid Red 52, Acid Orange 7, Acid Yellow Disperse Blue 1, Disperse Blue 3, Disperse Violet 1, Disperse Violet 4, HC Orange 1, HC Red 1, HC Red 1, Acid Yellow 10, Acid Yellow 36, Food Green 3, Pigment Red 57-1, Disperse Black 9, Disperse Blue 1 3, HC Red 13, HC Yellow 2, HC Yellow 4, Na Pikramat, 1, 4- Bis (2 '-hydroxyethyl) amino-2-nitro-p-phenylenediamine, HC Yellow 5, HC Blue 2, HC Blue 12, 4-amino-3-nitrophenol, HC Yellow 6, HC Yellow 12, 2-nitro 1- (2 'hydroxyethyl) amino-4
  • agents according to the invention 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 direct dyes which are sold under the trademark Arianor ® are, according to the invention also very particularly preferred cationic direct dyes.
  • the agents according to the invention according to this embodiment preferably contain the substantive dyes in an amount of 0.01 to 20 wt .-%, based on the total agent.
  • the preparations of the invention may also naturally occurring dyes such as henna red, henna neutral, henna black, chamomile, sandalwood, black tea, buckthorn bark, sage, bluewood, madder root, Catechu, Sedre and alkano root are included. It is not necessary for the oxidation dye precursors or the direct dyes to be in each case homogeneous compounds. Rather, in the inventive compositions, due to the production process for the individual dyes, in minor amounts, other components may be included, as far as they do not adversely affect the staining or other reasons, such as toxicological, must be excluded.
  • other components may be included, as far as they do not adversely affect the staining or other reasons, such as toxicological, must be excluded.
  • the agent according to the invention additionally contains a
  • B Compounds selected from (a) CH-acidic compounds, (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, (c) amino acids, (d) from 2 up to 9 amino acids oligopeptides.
  • Compounds according to the invention having a reactive carbonyl group 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) of alcohols to form acetals or ketals as a condensation compound.
  • 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, 4-hydroxy-3-methoxy-acetophenone, 3,5-dimethoxy-4- hydroxyacetophenone, 4-aminoacetophenone, 4-dimethylamino
  • Benzylideneacetone 4-hydroxybenzylideneacetone, 2-hydroxybenzylideneacetone, 4-methoxybenzylideneacetone, 4-hydroxy-3-methoxybenzylideneacetone, 4-dimethylaminobenzylideneacetone, 3,4-methylenedioxybenzylideneacetone, 4-pyrrolidinobenzylideneacetone, 4-piperidinobenzylideneacetone, 4-morpholinobenzylideneacetone, 4- Diethylaminobenzylideneacetone, 3-benzylidene-2,4-pentanedione, 3- (4'-hydroxybenzylidene) -2,4-pentanedione, 3- (4'-dimethylaminobenzylidene) -2,4-pentanedione, 2-benzylidenecyclohexanone, 2- (4 '-Hydroxybenzylidene) cyclohexanone, 2- (4'-dimethyl
  • 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-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
  • compositions according to the invention may contain further ingredients.
  • use of certain metal ions or complexes may be preferred to obtain intense colorations.
  • Agents according to the invention which additionally contain Cu, Fe, Mn, Ru ions or complexes of these ions are preferred here.
  • Preferred bleaching agents according to the invention additionally comprise Cu, Fe, Mn, Co, Ce, V, Ru or ions of complexes of these ions, with particularly preferred agents 0.0001 to 2.5 wt .-%, preferably 0.001 to 1 wt .-% of at least one compound from the group copper chloride (CuCl 2 ), copper sulfate (CuSO 4 ), iron (II) sulfate, manganese (II) sulfate, manganese (II) chloride, cobalt (II) chloride, cerium sulfate, cerium chloride , Vanadium sulfate, manganese dioxide (MnO 2 ).
  • compositions according to the invention may contain at least one ammonium compound from the group of ammonium chloride, ammonium carbonate, ammonium bicarbonate, ammonium sulfate and / or ammonium carbamate in an amount of from 0.5 to 10, preferably from 1 to 5,% by weight, based on the total composition of the composition ,
  • the bleaching according to the invention other active ingredients, excipients and additives such as nonionic polymers such as vinylpyrrolidone / vinyl acrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone / vinyl acetate copolymers and polysiloxanes, cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternary groups, dimethyldiallylammonium chloride polymers , Acrylamide-dimethyldiallyl-ammonium chloride copolymers, diethyl sulfate quaternized dimethylamino-ethylmethacrylate-vinylpyrrolidone copolymers, vinylpyrrolidone-imidazolinium methochloride copolymers and quaternized polyvinyl alcohol, zwitterionic and amphoteric polymers such as acrylamidopropyltrimethylammonium chloride / acrylate copolymers,
  • bentonite or fully synthetic hydrocolloids such as polyvinyl alcohol, structurants such as maleic acid and lactic acid, hair conditioning compounds such as phospholipids, such as soybean 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 bisabolol,
  • Vitamins, provitamins and vitamin precursors in particular those of groups A, B 3 , B 5 , B 6 ,
  • Plant extracts such as extracts of green tea, oak bark, stinging nettle, witch hazel,
  • Spruce needle horse chestnut, sandalwood, juniper, coconut, mango, apricot, lime,
  • Bodying agents such as sugar esters, polyol esters or polyol alkyl ethers,
  • Fats and waxes such as spermaceti, beeswax, montan wax and paraffins,
  • Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates,
  • Opacifiers such as latex, styrene / PVP and styrene / acrylamide copolymers
  • Pearlescing agents such as ethylene glycol mono- and distearate and PEG-3-distearate,
  • Propellants such as propane-butane mixtures, N 2 O, dimethyl ether, CO 2 and air, Antioxidants, included
  • compositions according to the invention may contain the ingredients in a suitable aqueous, alcoholic or aqueous-alcoholic carrier.
  • a suitable aqueous, alcoholic or aqueous-alcoholic carrier for the purpose of hair coloring such carriers are, for example, creams, emulsions, gels or surfactant-containing foaming solutions, such as shampoos, foam aerosols or other preparations which are suitable for use on the hair.
  • surfactant-containing foaming solutions such as shampoos, foam aerosols or other preparations which are suitable for use on the hair.
  • aqueous-alcoholic solutions are to be understood as meaning aqueous solutions containing from 3 to 70% by weight of a C 1 -C 4 -alkoxyethane, 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.
  • Preferred agents according to the invention are characterized in that they additionally contain a nonaqueous solvent, particularly preferred compositions according to the invention the solvent in a concentration of 0.1 to 30 weight percent, preferably in a concentration of 1 to 20 weight percent, most preferably in a concentration of 2 - 10 weight percent, each based on the agent included.
  • the solvent is selected from ethanol, n-propanol, isoropanol, n-butanol, propylene glycol, n-butylene glycol, glycerol, diethylene glycol monoethyl ether, diethylene glycol mono-n-butyl ether, phenoxyethanol and benzyl alcohol and mixtures thereof.
  • the pH of the compositions according to the invention can be adjusted within a wide range by suitable ingredients such as acidifying agent or alkalizing agent.
  • Oxidative dyeing of the fibers can in principle be carried out with atmospheric oxygen in the presence of oxidation dye precursors.
  • a chemical oxidizing agent used, especially if in addition to the coloring, a lightening effect on human hair is desired. This lightening effect may be desired regardless of the staining method. Accordingly, the presence of oxidation dye precursors is not a mandatory requirement for the use of oxidizing agents in the compositions according to the invention.
  • Suitable oxidizing agents are persulfates, chlorites and in particular hydrogen peroxide or its addition products of urea, melamine and sodium borate.
  • the oxidation colorant can also be applied to the hair together with a catalyst which promotes the oxidation of the dye precursors, e.g. by atmospheric oxygen, activated.
  • catalysts are e.g. Metal ions, iodides, quinones or certain enzymes.
  • 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 actual colorant is conveniently prepared immediately prior to use by mixing the preparation of the oxidizing agent with the preparation containing the compounds of formula I and optionally dye precursors.
  • 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 hair dye in a weakly alkaline medium.
  • the application temperatures can be in a range between 15 and 40 0 C. After a contact time of 5 to 45 minutes, the hair dye is removed by rinsing of the hair to be dyed. The washing with a shampoo is omitted if a strong surfactant-containing carrier, such as a dyeing shampoo was used.
  • an agent according to the invention may optionally be applied to the hair with additional dye precursors but also without prior mixing with the oxidation component. After an exposure time of 20 to 30 minutes, the oxidation component is then applied, if appropriate after an intermediate rinse. After a further exposure time of 10 to 20 minutes, the product is then rinsed and, if desired, shampooed again.
  • the corresponding agent is adjusted to a pH of about 4 to 7.
  • an air oxidation is initially desired, wherein the applied agent preferably has a pH of 7 to 10.
  • the use of acidified peroxydisulfate solutions may be preferred as the oxidizing agent.
  • compositions of the invention are mixed immediately before application with a hydrogen peroxide solution.
  • concentration of this hydrogen peroxide solution is determined on the one hand by the legal requirements and on the other hand by the desired effect; As a rule, 6-12% solutions in water are used.
  • the proportions of blonding agent and hydrogen peroxide solution are usually in the range 1: 1 to 1: 2, with an excess of hydrogen peroxide solution is particularly selected when no too pronounced Blondier Ober is desired.
  • Complex images are substances that can complex metal ions.
  • Preferred complexing agents are so-called chelate complexing agents, ie substances which form cyclic compounds with metal ions, where a single ligand occupies more than one coordination site on a central atom, ie at least " bidentate".
  • chelate complexing agents ie substances which form cyclic compounds with metal ions, where a single ligand occupies more than one coordination site on a central atom, ie at least " bidentate".
  • normally stretched compounds are closed by complex formation via an ion into rings. The number of bound ligands depends on the coordination number of the central ion.
  • Customary and preferred chelate complex images in the context of the present invention are, for example, polyoxycarboxylic acids, polyamines, ethylenediaminetetraacetic acid (EDTA), nitrilotriacetic acid (NTA) and hydroxyethanediphosphonic acids or their alkali metal salts.
  • complex-forming polymers ie polymers which carry functional groups either in the main chain itself or laterally to it, which can act as ligands and react with suitable metal atoms usually with the formation of chelate complexes, can be used according to the invention.
  • the polymer-bound ligands of the resulting metal complexes can originate from only one macromolecule or belong to different polymer chains. The latter leads to the crosslinking of the material, provided that the complex-forming polymers were not previously crosslinked via covalent bonds.
  • Complexing groups (ligands) of conventional complexing polymers are iminodiacetic acid, hydroxyquinoline, thiourea, guanidine, dithiocarbamate, hydroxamic acid, amidoxime, aminophosphoric acid, (cyclic) polyamino, mercapto, 1,3-dicarbonyl - And crown ether residues with z. T. very specific. Activities towards ions of different metals.
  • Base polymers of many also commercially important complex-forming polymers are polystyrene, polyacrylates, polyacrylonitriles, polyvinyl alcohols, polyvinylpyridines and polyethyleneimines. Natural polymers such as cellulose, starch or chitin are also complex-forming polymers. In addition, these can be provided by polymer-analogous transformations with other ligand functionalities.
  • Hydroxyl groups is at least 5,
  • polycarboxylic acids a) are understood as meaning carboxylic acids, including monocarboxylic acids, in which the sum of carboxyl and the hydroxyl groups contained in the molecule is at least 5.
  • Complexing agents from the group of nitrogen-containing polycarboxylic acids, in particular EDTA are preferred.
  • these complexing agents are at least partially present as anions. It is irrelevant whether they are introduced in the form of acids or in the form of salts.
  • alkali metal, ammonium or alkylammonium salts, in particular sodium salts are preferred.
  • polymeric aminodicarboxylic acids their salts or their precursors.
  • polyaspartic acids or their salts and derivatives which, in addition to cobuilder properties, also have a bleach-stabilizing action.
  • polyacetals which can be obtained by reacting dialdehydes with polyolcarboxylic acids which have 5 to 7 C atoms and at least 3 hydroxyl groups.
  • Preferred polyacetals are selected from dialdehydes such as glyoxal, Glutaraldehyde, terephthalaldehyde and mixtures thereof and from Polyolcarbon Textren such as Giucon Textre and / or glucoheptonic acid.
  • phosphonates are, in particular, hydroxyalkane or aminoalkanephosphonates.
  • hydroxyalkane phosphonates 1-hydroxyethane-1,1-diphosphonate (HEDP) is of particular importance. It is preferably used as the sodium salt, the disodium salt neutral and the tetrasodium salt alkaline (pH 9).
  • Preferred aminoalkane phosphonates are ethylenediamine tetramethylene phosphonate (EDTMP), diethylene triamine pentamethylene phosphonate (DTPMP) and their higher homologs. They are preferably in the form of neutral sodium salts, eg. B.
  • the complexing agent used here is preferably HEDP from the class of phosphonates.
  • the aminoalkanephosphonates also have a pronounced heavy metal binding capacity. Accordingly, in particular if the agents also contain bleach, it may be preferable to use aminoalkanephosphonates, in particular DTPMP, or to use mixtures of the phosphonates mentioned. These substances will be described below.
  • phosphonates preferably hydroxyalkane or aminoalkane phosphonates and in particular 1-hydroxyethane-1,1-diphosphonate (HEDP) or its di- or tetrasodium salt and / or ethylenediamine tetramethylene phosphonate (EDTMP) or its hexasodium salt and / or diethylene triamine pentamethylene phosphonate (DTPMP ) or its hepta- or octasodium salt.
  • HEDP 1-hydroxyethane-1,1-diphosphonate
  • ETMP ethylenediamine tetramethylene phosphonate
  • DTPMP diethylene triamine pentamethylene phosphonate
  • Particularly preferred agents according to the invention contain one or more substances from the group
  • NTA nitrilotriacetic acid
  • EDDG ethylenediamine-N-N'-diglutaric acid
  • HPDDS 2-Hydroxypropylenediamine-N-N'-dibemic acid
  • EDTA Ethylenediaminetetraacetic acid
  • ETC Ethylenedicysteic acid
  • DDS diaminoalkyldi (sulfosuccinic acid)
  • cyclodextrins preferred agents being phosphonates, preferably hydroxyalkane or aminoalkane phosphonates and especially 1-hydroxyethane-1,1-diphosphonate (HEDP) or its di- or tetrasodium salt and / or ethylenediamine tetramethylene phosphonate (EDTMP) or its hexasodium salt and or diethylenetriaminepentamethylenephosphonate (DTPMP) or its hepta- or octasodium salt.
  • HEDP 1-hydroxyethane-1,1-diphosphonate
  • ETMP ethylenediamine tetramethylene phosphonate
  • DTPMP diethylenetriaminepentamethylenephosphonate
  • preferred agents according to the invention additionally contain 0.1 to 25 wt.%, Preferably 0.5 to 20 wt.%, Particularly preferably 1 to 15 wt.% And in particular 1, 5 to 10 wt.% Of at least one substance from the groups of
  • Monoalkyl carbonates (carbonic acid monoesters) and / or
  • Carbonic acid monoamides and / or
  • Silylcarbamate Particularly suitable carbonates are ammonium, alkali metal and alkaline earth metal carbonates and bicarbonates.
  • alkali metal and alkaline earth metal carbonates and bicarbonates.
  • sodium bicarbonate, sodium carbonate are particularly preferred.
  • compositions according to the invention may preferably also contain at least one carbonic acid monoester and / or at least one carbonic acid monoamide. These substances are described in detail below.
  • Agents preferred according to the invention are characterized in that they contain at least one carbonic acid monoester of the formula (I)
  • R represents a saturated or unsaturated, straight-chain, branched, or cyclic, substituted or unsubstituted hydrocarbon radical, or a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocycle.
  • R preferably represents a substituted or unsubstituted, straight-chain or branched alkyl, alkenyl or alkynyl radical, preference being given to hydroxy, amino, nitro, sulfonic acid groups or halogens as substituents.
  • Further preferred radicals R are phenyl and benzyl radicals and further substituted representatives. More preferably, R is a C 1-6 alkyl group. Examples of inventive The groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, iso-pentyl and hexyl.
  • radical R in formula (I) is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl as well as hydroxymethyl and hydroxyethyl radicals.
  • compositions according to the invention may contain carbonic acid monoamides.
  • preferred agents according to the invention are characterized in that they contain at least one carbonic acid monoamide of the formula (II)
  • R preferably represents a substituted or unsubstituted, straight-chain or branched alkyl, alkenyl or alkynyl radical, preference being given to hydroxy, amino, nitro, sulfonic acid groups or halogens as substituents.
  • Further preferred radicals R are phenyl and benzyl radicals and further substituted representatives. More preferably R is a Cv ⁇ -alkyl group.
  • C-i-C ⁇ -alkyl groups are the groups methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl and hexyl.
  • radical R in formula (II) is selected from methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, fe / t Butyl and hydroxymethyl and hydroxyethyl radicals.
  • the acidic H atom of the carbonic acid monoester or monoamide may also be in neutralized form, i. salts of carbonic acid monoesters or carbonic acid monoamides can also be used according to the invention.
  • agents according to the invention are preferred which contain the carbonic acid monoester or the carbonic acid monoamide in completely or partially neutralized form, preferably in the form of its alkali metal, ammonium, alkaline earth metal or aluminum salt and in particular in the form of its sodium salt.
  • compositions according to the invention comprise one or more carbonic acid monoesters and / or one or more carbonic acid monoamides
  • agents according to the invention are preferred which contain the carbonic acid monoester and / or carbonic acid monoamides in amounts of from 0.1 to 20% by weight, preferably from 0 , 5 to 18 wt.%, Particularly preferably from 2 to 15 wt.% And in particular from 5 to 12 wt.%, Each based on the total agent.
  • compositions according to the invention may preferably also contain at least one silyl carbonate and / or at least one silyl carbamate. These substances are described in detail below. Agents preferred according to the invention are characterized in that they contain at least one silyl carbonate of the formula (III)
  • radicals R 1 , R 2 and R 3 independently of one another represent a hydrogen atom, a saturated or unsaturated, straight-chain, branched or cyclic, substituted or unsubstituted hydrocarbon radical or for a trialkylsilyl group, preferably a trimethylsilyl group or for a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocycle or a halogen, a substituted or unsubstituted hydroxy, oxo, amino, imino groups and the radical R 4 is a chemical bond to the Si atom or to one of the radicals R 1 , R 2 or R 3 , a hydrogen atom, a saturated or unsaturated, straight-chain, branched, or cyclic, substituted or unsubstituted hydrocarbon radical or for a substituted or unsubstituted SiIyI or alumino group or for a substituted or unsubstituted aryl group
  • Preferred radicals R 1 , R 2 and R 3 in the abovementioned formula (III) are substituted or unsubstituted, straight-chain or branched alkyl radicals.
  • the alkyl radicals having 1 to 5 carbon atoms and the hydroxyalkyl radicals are preferred, so that preferred agents according to the invention are characterized in that the radicals R 1 , R 2 and R 3 in formula (I) are selected from methyl, ethyl, n Propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, hydroxymethyl and hydroxyethyl radicals.
  • Preferred radicals R 4 in the abovementioned formula (III) are hydrogen, substituted or unsubstituted, straight-chain or branched alkyl radicals and trialkylsilyl radicals. Among them, preferred are hydrogen, methyl, ethyl, tert-butyl and trimethylsilyl radicals.
  • agents according to the invention are preferred which comprise at least one silyl carbonate in completely or partially neutralized form, preferably in the form of its alkali metal, ammonium, alkaline earth metal or aluminum salt and in particular in the form of its sodium salt.
  • the compositions of the invention may contain silyl carbamates.
  • Agents preferred according to the invention are characterized in that they contain a silyl carbamate of the formula (IV)
  • radicals R 1 , R 2 and R 3 independently of one another represent a hydrogen atom, a saturated or unsaturated, straight-chain, branched or cyclic, substituted or unsubstituted hydrocarbon radical or for a trialkylsilyl group, preferably a trimethylsilyl group or a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocycle or a halogen, a substituted or unsubstituted hydroxy, oxo, amino groups and the radicals R 4 and R 5 independently of one another for a chemical bond to the Si atom or to a the radicals R 1 , R 2 or R 3 , a hydrogen atom, a saturated or unsaturated, straight-chain, branched or cyclic, substituted or unsubstituted hydrocarbon radical or a substituted or unsubstituted SiIyI or alumino group or a substituted or unsubstituted
  • Preferred radicals R 1 , R 2 and R 3 in the abovementioned formula (IV) are substituted or unsubstituted, straight-chain or branched alkyl radicals.
  • the alkyl radicals having 1 to 5 carbon atoms and the hydroxyalkyl radicals are preferred, so that preferred agents according to the invention are characterized in that the radicals R 1 , R 2 and R 3 in formula (II) are selected from methyl, ethyl, n Propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, hydroxymethyl and hydroxyethyl radicals.
  • Preferred radicals R 4 and R 5 in the abovementioned formula (IV) are hydrogen, substituted or unsubstituted, straight-chain or branched alkyl radicals and trialkylsilyl radicals. Among them, preferred are hydrogen, methyl, ethyl, tert-butyl and trimethylsilyl radicals.
  • compositions according to the invention contain one or more silyl carbonates and / or one or more silyl carbamates
  • agents according to the invention are preferred which contain the silyl carbonate (s) and / or silyl carbamate (s) in amounts of from 0.1 to 25% by weight .%, Preferably from 0.5 to 20 wt.%, Particularly preferably from 1 to 15 wt.% And in particular from 1, 5 to 10 wt.%, Each based on the total agent.
  • the agents according to the invention preferably have a pH of from 5.0 to 9.0, preferably from 5.5 to 8.0, particularly preferably from 6.0 to 7.7, more preferably from 6.2 to 7.2 and especially from 6.5 to 6.8.
  • Preferred agents according to the invention are formulated with little or no water. Particularly preferred agents according to the invention are characterized in that they contain less than 5% by weight, preferably less than 2% by weight, more preferably less than 1% by weight and in particular less than 0.5% by weight of water, preferred agents being anhydrous.
  • the water content of the agent can be determined, for example, by means of titration according to Karl Fischer.
  • a second object of the present invention is a method for lightening
  • Keratinmaschinen in particular human hair, in which, if desired, a pretreatment agent M1 is applied to the fiber, then a means M2 is applied to the fiber, wherein, if desired, the means
  • this agent M2 is added before use another agent M3, this agent M2 is rinsed from the fiber after a period of 5-30 minutes and after treatment optionally a post-treatment agent M4 applied to the fiber and rinsed after a contact time of a few minutes, wherein at least one of the means M1, M2 or M3 is an agent according to the invention.
  • the agents according to the invention can therefore be formulated as one-component agents (bleaching agent M2 or aftertreatment agent M4), as two-component agents (M2 + M3) or as three-component agents (M2 + M3 + M4) and used accordingly. Separation into multicomponent systems is particularly suitable where incompatibilities of the ingredients are to be expected or feared; the agent to be used in such systems is manufactured by the consumer just prior to use by mixing the component. A whitening process in which the whitening cream and the oxidizing agent are initially separate is preferred.
  • a further subject of the present invention is therefore a process for whitening human hair, in which an aqueous-based composition containing hydrogen peroxide is mixed with an agent according to the invention to form a homogeneous composition and applied to the hair.
  • the aqueous composition contains from 1 to 20% by weight, preferably from 2 to 10% by weight and in particular from 3 to 6% by weight of hydrogen peroxide, calculated as 100% H 2 O 2 .
  • aqueous-based composition comprising hydrogen peroxide is mixed with an agent according to the invention in a weight ratio of 1: 5 to 10: 1, preferably 1: 2 to 5: 1 and in particular 1: 2 to 2: 1 mixed into a homogeneous composition, and this is applied to the hair.
  • Another object of the present invention is therefore a process for whitening human hair, wherein an aqueous composition containing hydrogen peroxide, with a further agent containing preferably at least one alkalinity donor and / or direct hair dye and / or at least one oxidation dye precursor, and a Mixture of the invention mixed to form a homogeneous composition, and this is applied to the hair.
  • Another object of the present invention is the use of mixtures of a) at least one solid peroxo compound, which is selected from ammonium and alkali metal persulfates and peroxidisulfates, b1) at least one cyanate of the formula
  • H 2 NC (O) -L in which L stands for a group displaceable by the anion " OOH, in bleaching agents, preferably in weakly alkaline to neutral bleaching agents.
  • the use of the mixtures is the achievement of certain advantageous
  • Preferred according to the invention are uses for i. Increase in the whitening or bleaching performance and / or ii. Increase the skin compatibility of brightening or bleaching agents.
  • the mutated mutandis applies to the preferred agents.
  • Titanium dioxide 0.3 0.3 0.3
  • Aerosil 200 0.1 0.1 0.1
  • Aerosil ® 200 Fumed Silica (INCI name: Silica) (Degussa) Cekol ® Carboxymethylcellulose (INCI name Cellulose Gum) (CP Kelco)
  • Turpinal SL 1.5% by weight hydrogen peroxide 12.0% by weight ammonia solution; 25% 0.65% by weight Acrysol 33 12.0% by weight water ad 100% by weight
  • Texapon ® N28 lauryl ether sulfate sodium salt (at least 26.5%
  • Formulations 1 to 3 were mixed with the developer dispersion in a weight ratio of 1: 3 and, after mixing with phosphoric acid, adjusted to a pH of between 7 and 7.5.
  • a comparative bleaching powder according to the invention was prepared, the composition of which (in g) is given in Table 1: Components V1 E4
  • Aerosil 200 3.0 3.0
  • Aerosil ® 200 fumed silica (INCI E 3ezeic

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Abstract

La présente invention concerne des agents pour blondir les cheveux/poils d'une personne, qui contiennent, rapportés à leur poids, 5 à 70 % en poids d'au moins un composé peroxo solide qui est choisi parmi les persulfates et peroxysulfates d'ammonium et de métaux alcalins, et 0,05 à 5 % en poids d'au moins un cyanate de formule M+ [OCN]- dans laquelle M+ est K+, Na+, Li+ ou NH4+ ou 1/2 Ca2+, 1/2 Mg2+ ou 1/2 Zn2+ et/ou 0,05 à 5 % en poids d'au moins un composé de formule H2N-C(O)-L dans laquelle L est un groupe qui peut être substitué par l'anion -OOH. Ces agents se caractérisent par une réduction de leur temps d'action et de leur potentiel d'irritation.
PCT/EP2007/002527 2006-04-07 2007-03-22 Agents d'éclaircissement et/ou de coloration bien tolérés par la peau Ceased WO2007115657A2 (fr)

Applications Claiming Priority (2)

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DE102006016817.8 2006-04-07
DE200610016817 DE102006016817A1 (de) 2006-04-07 2006-04-07 Aufhell- und/oder Färbemittel mit guter Hautverträglichkeit

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1882495A3 (fr) * 2006-07-28 2010-08-18 Henkel AG & Co. KGaA Activation de peroxyde d'hydrogène avec des tensioactifs anioniques
CN102786433A (zh) * 2012-03-15 2012-11-21 浙江康恩贝制药股份有限公司 一种延胡索酰胺类化合物提取物及其制备方法和应用
US9248080B2 (en) 2011-05-20 2016-02-02 L'oreal Process for bleaching keratin fibres comprising the application of a composition in compressed form
CN115867358A (zh) * 2020-06-17 2023-03-28 汉高股份有限及两合公司 用于氧化性毛发淡化剂的增稠碱化组分

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2975290B1 (fr) * 2011-05-20 2013-08-09 Oreal Composition de decoloration des fibres keratiniques sous forme de tablette avec persulfate et un polymere particulier
FR2975291B1 (fr) * 2011-05-20 2013-11-08 Oreal Composition de decoloration des fibres keratiniques sous forme de tablette avec persulfate et un sel d'ammonium

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Publication number Priority date Publication date Assignee Title
DE1138511B (de) * 1959-07-07 1962-10-25 Colgate Palmolive Co Haarpflegemittel
GB2175621B (en) * 1985-05-28 1989-07-05 Lion Corp Bleaching compositions
DE10206292A1 (de) * 2002-02-15 2003-08-28 Wella Ag Verfahren zur dauerhaften Haarverformung mit verzögertem Reaktionsstart des Reduktionsmittels
EP1503725B1 (fr) * 2002-03-28 2015-09-30 The Procter & Gamble Company Produit de decoloration des cheveux
US6821302B2 (en) * 2002-11-01 2004-11-23 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Permanent coloring of hair using carbonate salts and bicarbonate salts and using percarbamic acid precursors
DE20303559U1 (de) * 2003-03-06 2003-08-28 L'Avant Garde Inc., Simi Valley, Calif. Mittel zum gleichzeitigen Färben und Aufhellen von Keratinfasern
DE10339164A1 (de) * 2003-08-26 2005-03-31 Henkel Kgaa Stabilisierung von Wasserstoffperoxid während der Auflösung alkalisierend wirkender Feststoffe in wasserstoffperoxidhaltigen Systemen
DE102005053850A1 (de) * 2005-11-09 2007-05-10 Henkel Kgaa Wasserfreie Zusammensetzungen und daraus herstellbare Mittel

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1882495A3 (fr) * 2006-07-28 2010-08-18 Henkel AG & Co. KGaA Activation de peroxyde d'hydrogène avec des tensioactifs anioniques
US9248080B2 (en) 2011-05-20 2016-02-02 L'oreal Process for bleaching keratin fibres comprising the application of a composition in compressed form
CN102786433A (zh) * 2012-03-15 2012-11-21 浙江康恩贝制药股份有限公司 一种延胡索酰胺类化合物提取物及其制备方法和应用
CN115867358A (zh) * 2020-06-17 2023-03-28 汉高股份有限及两合公司 用于氧化性毛发淡化剂的增稠碱化组分

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