WO2015185264A1 - Agent éclaircissant à hydrolysats de kératine cationiques - Google Patents

Agent éclaircissant à hydrolysats de kératine cationiques Download PDF

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Publication number
WO2015185264A1
WO2015185264A1 PCT/EP2015/058717 EP2015058717W WO2015185264A1 WO 2015185264 A1 WO2015185264 A1 WO 2015185264A1 EP 2015058717 W EP2015058717 W EP 2015058717W WO 2015185264 A1 WO2015185264 A1 WO 2015185264A1
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Prior art keywords
amino
cationic
packaging unit
cosmetic
weight
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PCT/EP2015/058717
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German (de)
English (en)
Inventor
Sylvia KERL
Matthias Schweinsberg
Erik Schulze Zur Wiesche
Susanne Bietz
Camille Grosjacques
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Henkel Ag & Co. Kgaa
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Publication of WO2015185264A1 publication Critical patent/WO2015185264A1/fr

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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
    • A61Q5/10—Preparations for permanently dyeing 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/65—Collagen; Gelatin; Keratin; Derivatives or degradation products thereof
    • 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
    • A61K2800/882—Mixing prior to application

Definitions

  • the present invention relates to a kit of parts containing a cosmetic agent containing at least one cationic keratin hydroxylate and an oxidizing agent preparation containing a specific amount of oxidizing agent.
  • the present invention relates to a method for dyeing keratinic fibers using the packaging unit according to the invention.
  • the present invention relates to the use of the packaging unit according to the invention for increasing the care keratinischer fibers.
  • the change in the shape and color of hair represents an important area of modern cosmetics.
  • the appearance of the hair can be adapted to current fashion trends as well as to the individual needs of the individual consumer.
  • the fashionable color design of hairstyles or the lamination of gray or white hair with fashionable or natural tones is usually done with color-changing agents. In addition to the desired dyeing power, these agents should cause the least possible damage to the hair, and preferably possess additional care properties.
  • oxidation colorants For permanent, intensive colorations with corresponding fastness properties, so-called oxidation colorants are used. Such 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, however, it is usually necessary to use a mixture of a larger number of oxidation dye precursors; In many cases, direct dyes are still used for shading.
  • the dyes formed or used directly in the course of color formation have significantly different fastnesses (eg UV stability, perspiration fastness, wash fastness, etc.), then over time they can become one recognizable and mostly undesirable color shift come. This phenomenon is more pronounced when staining hairs or haircuts with different degrees of damage. An example of this is long hair, in which the hair tips are usually much more damaged than the freshly regrown hair zones.
  • fastnesses eg UV stability, perspiration fastness, wash fastness, etc.
  • dyeing or tinting agents which contain so-called direct drawers as coloring component. These are dye molecules that grow directly onto the substrate and do not require an oxidative process to form the paint. 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 oxidative dyeings, so that much earlier an often undesirable change in shade or a visible homogeneous color loss occurs.
  • precursors of the natural hair dye melanin are applied to the substrate, e.g. Hair, applied; These then form naturally-analogous dyes in the course of oxidative processes in the hair.
  • 5,6-dihydroxyindoline is used as the dye precursor.
  • the coloration can be carried out with atmospheric oxygen as the sole oxidant, so that can be dispensed with further oxidizing agent.
  • 5,6-dihydroxyindoline can be used as the sole dye precursor.
  • satisfactory results can often only be achieved for use in persons with originally red and, in particular, dark to black hair color, by using other dye components, in particular special oxidation dye precursors.
  • oxidative hair dyes are disadvantageous to the user despite their advantageous dyeing properties.
  • the use of the oxidizing agent for coloration or development of the actual dyeing leads to damage in the hair structure and on the hair surface.
  • the hair becomes brittle, its elasticity decreases and the combability decreases.
  • oxidative colorants generally require a basic pH for the coloration, in particular between pH 9.0 and pH 11.5. These pH values are necessary to ensure an opening of the outer cuticle (cuticle) and to allow penetration of the dye precursors and / or the oxidizing agent into the hair.
  • the spreading of the outer cuticle layer leads to an unpleasant surface sensation of the hair and thus to a deteriorated combability in the wet and dry state.
  • additional aftertreatment agents such as conditioning agents.
  • a first subject of the present invention is therefore a kit of parts for the coloring of keratinous fibers, comprising - made up separately - a) at least one container (C1) containing a cosmetic agent (M1) containing at least one cationic keratin hydrolyzate , at least one oxidation dye precursor and at least one alkalizing agent, and
  • M2 oxidizing agent preparation
  • keratinic fibers or also keratin fibers is understood to mean furs, wool, feathers and human hair, In the context of the present invention it is particularly preferred if the cosmetic agents are used for dyeing human hair.
  • the term "container” is understood to mean an envelope which is present in the form of an optionally resealable bottle, tube, can, sachet, sachet or similar wrappings However, these are enclosures made of glass or plastic.
  • combability in the context of the present invention means both the combability of the wet fiber and the combability of the dry fiber.
  • fatty alcohols in the context of the present invention is understood as meaning aliphatic, long-chain, monohydric, primary alcohols which have unbranched hydrocarbon radicals having 6 to 30 carbon atoms
  • the hydrocarbon radicals may be saturated but also mono- or polyunsaturated.
  • fatty acids in the context of the present invention is understood as meaning aliphatic monocarboxylic acids with unbranched carbon chain which have hydrocarbon radicals having 6 to 30 carbon atoms
  • the hydrocarbon radicals can be either saturated or mono- or polyunsaturated.
  • the indication of the total amount in relation to the components of the cosmetic agent (M1) and the oxidation preparation (M2) relates in the present case - unless stated otherwise - to the total amount of active substance of the respective component. Furthermore, the indication of the total amount with respect to the components of the cosmetic product (M1), unless stated otherwise, refers to the total weight of the oxidant-free cosmetic product.
  • the cosmetic agents (M1) in the first container (C1) of the packaging unit according to the invention contain a cosmetic carrier.
  • the cosmetic carrier is preferably aqueous, alcoholic or aqueous-alcoholic.
  • creams, emulsions, gels or surfactant-containing foaming solvents can be used in the context of the present invention.
  • solutions, such as shampoos, foam aerosols or other preparations which are suitable for use on the hair, can be used.
  • an aqueous carrier contains at least 30% by weight, in particular at least 50% by weight, of water, based on the total weight of the cosmetic product.
  • aqueous-alcoholic carriers are water-containing compositions comprising a C 1 -C 4 alcohol in a total amount of from 3 to 90% by weight, based on the total weight of the cosmetic agent, in particular ethanol or isopropanol.
  • the cosmetic agents (M1) may additionally contain other organic solvents, such as methoxybutanol, ethyldiglycol, 1, 2-propylene glycol, n-propanol, n-butanol, n-butylene glycol, glycerol, diethylene glycol monoethyl ether, and diethylene glycol mono-n-butyl ether. Preference is given to all water-soluble organic solvents, wherein the solvent in a total amount of 0.1 to 30 wt .-%, preferably from 1 to 20 wt .-%, in particular from 2 to 10 wt .-%, based on the total weight of cosmetic agent, is included.
  • organic solvents such as methoxybutanol, ethyldiglycol, 1, 2-propylene glycol, n-propanol, n-butanol, n-butylene glycol, glycerol, diethylene glycol monoethyl ether, and diethylene glyco
  • the cosmetic agent (M1) of the packaging unit according to the invention contains at least one cationic keratin hydrolyzate.
  • the cationic keratin hydrolyzate used in the context of the present invention has sufficient stability against various pH values and strongly oxidizing substances and therefore ensures a care effect as well as improved chroma of shades even under harsh chemical conditions which occur during oxidative hair coloring.
  • the keratin hydrolysates on which the cationic keratin hydrolysates used in the context of the present invention can be prepared from keratin by chemical, in particular alkaline or acid hydrolysis, by enzymatic hydrolysis and / or by a combination of the two types of hydrolysis.
  • hydrolytic enzymes are suitable, such as alkaline proteases.
  • the hydrolysis of keratins usually gives a keratin hydrolyzate having a molecular weight distribution of about 75 daltons to several thousand daltons.
  • cationic total hydrolysates of keratins have also proved to be preferred.
  • the at least one cationic keratin hydrolyzate is a cationic keratin hydrolyzate of sheep wool.
  • the at least one cationic keratin hydrolyzate one or more radical (s) of the formula R-N + (CH3) 2-CH2-CH (OH) -CH 2 -X, in which R represents a C 4 alkyl -2O or a Ci4-2o alkenyl group, X is O, NH or S and R is a hydrolyzed keratin residue on.
  • the cationization of the keratin hydrolysates with the above-described radicals can be achieved by reacting the keratin hydrolysates with the corresponding halides of the above formula, the above-described radicals being bonded to the keratin hydrolyzate via ether and / or ester and / or amide and / or amine bonds could be.
  • the at least one cationic keratin hydrolyzate has one or more steardimonium hydroxypropyl group (s).
  • the use of the special cationic keratin hydrolysates results in a significant improvement in care performance, especially combability and entanglement.
  • these particular cationic Keratinhydrolysate have sufficient stability against the oxidizing agents used in brightening oxidative colorants and pH values and can be easily incorporated into the cosmetic products.
  • the at least one cationic keratin hydrolyzate preferably has a weight-average molecular weight M w of from 100 to 10,000 Da, preferably from 150 to 8,000 Da, preferably from 200 to 6,000 Da, in particular from 300 to 5,000 Da.
  • the weight-average molecular weight M w can be determined, for example, by gel permeation chromatography (GPC) using polystyrene as an internal standard in accordance with DIN 55672-3
  • the at least one cationic keratin hydrolyzate is in a total amount of 0.01 to 5 wt .-%, preferably from 0.05 to 3.75 wt .-%, preferably from 0.1 to 2.5 Wt .-%, more preferably from 0.3 to 2 wt .-%, in particular from 0.4 to 1, 3 wt .-%, based on the total weight of the cosmetic composition containing.
  • the use of the at least one cationic keratin hydrolyzate in the abovementioned amounts results in a positive influence on the care performance, in particular the combability and the entanglement of keratinic fibers, which have been treated with oxidative brighteners prepared from the packaging unit according to the invention.
  • the use of the abovementioned amounts of the at least one cationic keratin hydrolyzate avoids a negative influence on further ingredients and the stability of the cosmetic agents (M1).
  • the cosmetic agents (M1) of the packaging unit according to the invention contain as further constituent at least one oxidation dye precursor.
  • Oxidation dye precursors can due to their reaction behavior are divided into two categories, so-called developer components and coupler components.
  • the cosmetic compositions of the present invention contain at least one type of oxidation dye precursor of the developer type.
  • the cosmetic compositions according to the invention comprise at least one coupler type oxidation dye precursor. Particularly good results with regard to the coloring of keratinic fibers are obtained when the cosmetic agents (M1) comprise at least one developer-type oxidation dye precursor and at least one coupler-type oxidation dye precursor.
  • the developer and coupler components are usually used in free form.
  • cosmetic agents (M1) are preferred which contain the developer and / or coupler components in a total amount of from 0.001 to 10% by weight, preferably from 0.01 to 8% by weight, preferably from 0.1 to 5% by weight .-%, in particular from 0.5 to 3 wt .-%, based on the total weight of the cosmetic agent.
  • the cosmetic agent (M1) is therefore characterized in that it comprises a developer and / or coupler-type oxidation dye precursor in a total amount of from 0.001 to 10% by weight, preferably from 0.01 to 8% by weight, preferably from 0.1 to 5 wt .-%, in particular from 0.5 to 3 wt .-%, based on the total weight of the cosmetic composition contains.
  • Suitable oxidation dye precursors of the developer type are, for example, p-phenylenediamine and its derivatives.
  • Preferred p-phenylenediamines are selected from one or more compounds of the group which is formed from p-phenylenediamine, p-toluenediamine, 2-chloro-p-phenylenediamine, 2,3-dimethyl-p-phenylenediamine, 2,6-dimethyl p-phenylenediamine, N, N-bis (2-hydroxy-ethyl) -p-phenylenediamine, 2- (2-hydroxyethyl) -p-phenylenediamine, 2- (1,2-dihydroxyethyl) -p-phenylenediamine, N- (2-hydroxypropyl) -p-phenylenediamine, N- (4'-aminophenyl) -p-phenylenediamine, 2-methoxymethyl-p-phenylenediamine, N-phen
  • developer component compounds which contain at least two aromatic nuclei which are reacted with amino and / or hydroxyl groups. groups are substituted.
  • Preferred binuclear developer components are selected from N, N'-bis (2-hydroxyethyl) -N, N'-bis (4'-aminophenyl) -1,3-diaminopropan-2-ol, N, N'-bis- (4-aminophenyl) - 1, 4-diazacycloheptane, bis (2-hydroxy-5-aminophenyl) methane and their physiologically acceptable salts.
  • p-aminophenol derivative or one of its physiologically tolerable salts.
  • Preferred p-aminophenols are p-aminophenol, N-methyl-p-aminophenol, 4-amino-3-methylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- (1, 2-dihydroxyethyl) phenol, 4-amino-2- (diethylaminomethyl) phenol and their physiologically acceptable salts.
  • the developer component may be selected from o-aminophenol and its derivatives, preferably from 2-amino-4-methylphenol, 2-amino-5-methylphenol, 2-amino-4-chlorophenol and / or their physiologically acceptable salts.
  • the developer component may be selected from heterocyclic developer components, such as pyrimidine derivatives, pyrazole derivatives, pyrazolopyrimidine derivatives or their physiologically acceptable salts.
  • Preferred pyrimidine derivatives are 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine and their physiologically acceptable salts.
  • a preferred pyrazole derivative is 4,5-diamino-1- (2-hydroxyethyl) pyrazole and its physiologically acceptable salts.
  • pyrazolopyrimidines in particular pyrazolo [1, 5-a] pyrimidines are preferred.
  • Preferred oxidation dye precursors of the developer type are selected from the group formed from p-phenylenediamine, p-toluenediamine, 2- (2-hydroxyethyl) -p-phenylenediamine, 2- (1, 2-dihydroxyethyl) -p-phenylenediamine, N, N-bis- (2-hydroxyethyl) -p-phenylenediamine, 2-
  • Methoxymethyl-p-phenylenediamine N- (4-amino-3-methylphenyl) -N- [3- (1 H -imidazol-1-yl) -propyl] amine, N, N'-bis (2-hydroxy-ethyl ) -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, 1, 10-bis (2,5-diaminophenyl) -1, 4J , 10-tetraoxadecane, p-aminophenol, 4-amino-3-methylphenol, 4-amino-2-amino-methylphenol, 4-amino-2- (1, 2-dihydroxyeth
  • the cosmetic agent (M1) as oxidation dye precursor additionally contains, in addition to at least one developer component, additionally at least one coupler component.
  • the coupler components m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenol derivatives are generally used.
  • Coupler components preferred according to the invention are selected from
  • (F) pyridine derivatives in particular 3-amino-2-methylamino-6-methoxypyridine, 2,6-diaminopyridine, 2,6-dihydroxy-3,4-dimethylpyridine, 2-amino-3-hydroxypyridine and 3,5-diamino 2,6-dimethoxy-pyridine,
  • Coupler components preferred according to the invention are selected from the group formed from 3-aminophenol, 5-amino-2-methylphenol, 3-amino-2-chloro-6-methylphenol, 2-hydroxy-4-aminophenoxyethanol, 5-amino-4 -chloro-2-methylphenol, 5- (2-hydroxyethyl) amino-2-methylphenol, 2,4-dichloro-3-aminophenol, 2-aminophenol, 3-phenylenediamine, 2- (2,4-diaminophenoxy) ethanol, 1,3-bis (2,4-diaminophenoxy) propane, 1-methoxy-2-amino-4- (2-hydroxyethylamino) benzene, 1,3-bis (2,4-diaminophenyl) propane, 2.6 Bis (2'-hydroxyethylamino) -1-methylbenzene, 2 - ( ⁇ 3 - [(2-hydroxyethyl) amino] -4- methoxy-5-methylphenyl ⁇ amino) ethanol, 2 -
  • 2-amino-3-hydroxypyridine 3-amino-2-methylamino-6-methoxypyridine, 2,6-dihydroxy-3,4-dimethylpyridine, 3,5-diamino-2,6-dimethoxypyridine, 1-phenyl-3-ol methylpyrazol-5-one, 1-naphthol, 1,5-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 1-dihydroxynaphthalene, 1,8-dihydroxynaphthalene, 4-hydroxyindole, 6-hydroxyindole, 7-hydroxyindole, 4-hydroxyindoline, 6 -Hydroxyindoline, 7-hydroxyindoline or the physiologically acceptable salts of the aforementioned compounds.
  • coupler components according to the invention are resorcinol, 2-methylresorcinol, 5-amino-2-methylphenol, 3-aminophenol, 2- (2,4-diaminophenoxy) ethanol, 1,3-bis- (2,4-diamino-phenoxy) propane , 1-Methoxy-2-amino-4- (2'-hydroxyethylamino) benzene, 2-amino-3-hydroxypyridine, 2,6-dihydroxy-3,4-dimethylpyridine, 1, 5-dihydroxynaphthalene, 2,7-dihydroxynaphthalene and 1-naphthol and their physiologically acceptable salts.
  • the cosmetic agents (M1) are characterized in that they contain as oxidation dye precursor at least one developer and / or coupler component from the group which is formed from p-phenylenediamine, p-toluenediamine, 2- (2-hydroxyethyl) p-phenylenediamine, 2- (1,2-dihydroxyethyl) -p-phenylenediamine, N, N-bis (2-hydroxyethyl) -p-phenylenediamine, 2-methoxymethyl-p-phenylenediamine, N- (4-aminobenzyl) 3-methylphenyl) -N- [3- (1H-imidazole)
  • Developer-type and coupler-type oxidation dye precursors are preferably used in certain combinations.
  • the following combinations have proved to be particularly advantageous: p-toluenediamine / resorcinol; p-toluenediamine / 2-methylresorcinol; p-toluenediamine / 5-amino-2-methylphenol; p-toluenediamine / 3-aminophenol; p-toluylenediamine / 2- (2,4-diaminophenoxy) ethanol; p-toluenediamine / 1,3-bis (2,4-diaminophenoxy) propane; p-toluenediamine / 1-methoxy-2-amino-4- (2-hydroxyethylamino) benzene; p-toluenediamine / 2-amino-3-hydroxypyridine; p-toluenediamine / 1-naphthol; 2- (2-hydroxyeth
  • the cosmetic agents (M1) additionally contain at least one substantive dye.
  • Direct dyes are dyes that are applied directly to the hair and do not require an oxidative process to form the dye. Direct dyes are usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
  • Direct dyes can be subdivided into anionic, cationic and nonionic substantive dyes.
  • Preferred anionic substantive dyes are those referred to as Acid Yellow 1, Yellow 10, Acid Yellow 23, Acid Yellow 36, Acid Orange 7, Acid Red 33, Acid Red 52, Pigment Red 57: 1, Acid Blue 7, Acid Green 50, Acid Violet 43, Acid Black 1, Acid Black 52 and tetrabromophenol blue known compounds.
  • Preferred cationic substantive dyes are cationic triphenylmethane dyes, such as Basic Blue 7, Basic Blue 26, Basic Violet 2 and Basic Violet 14, aromatic systems which are substituted by a quaternary nitrogen group, such as Basic Yellow 57, Basic Red 76, Basic Blue 99, Basic Brown 16 and Basic Brown 17 and HC Blue 16, as well as Basic Yellow 87, Basic Orange 31 and Basic Red 51.
  • Preferred nonionic substantive dyes are HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, HC Orange 1, Disperse Orange 3, HC Red 1, HC Red 3, HC Red 10, HC Red 1 1.
  • direct dyes also naturally occurring dyes can be used, as for example in henna red, henna neutral, henna black, chamomile flower, Sandalwood, black tea, walnut, buckthorn bark, sage, bluewood, madder root, catechu and alcano root are included.
  • the cosmetic agent (M1) contains the substantive dyes in a total amount of 0.001 to 10 wt .-%, preferably from 0.01 to 8 wt .-%, preferably from 0.1 to 5 wt .-%, in particular from 0 , 5 to 3 wt .-%, based on the total weight of the cosmetic product.
  • the cosmetic agents (M1) of the packaging unit according to the invention comprise at least one alkalizing agent, which may be inorganic or organic.
  • the cosmetic agents (M1) generally have a basic pH, in particular between pH 8.0 and pH 12. These pHs are required to ensure opening of the outer cuticle (cuticle) and to allow penetration of the oxidation dye precursors and / or the oxidizing agent into the hair.
  • Preferred inorganic alkalizing agents are selected from the group consisting of ammonia or ammonium hydroxide, ie aqueous solutions of ammonia, sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, sodium phosphate, potassium phosphate, sodium silicate, potassium silicate, sodium carbonate and potassium carbonate and mixtures thereof.
  • Ammonia or ammonium hydroxide is a particularly preferred alkalizing agent. Particular preference is given to containing ammonia in a total amount of from 0.1 to 20% by weight, preferably from 0.5 to 10% by weight, in particular from 1 to 7% by weight, based on the total weight of the cosmetic composition.
  • Preferred organic alkalizing agents are selected from at least one alkanolamine.
  • Alkanolamines which are preferred according to the invention are selected from alkanolamines of primary, secondary or tertiary amines having a C 2 -C 6 -alkyl basic body which carries at least one hydroxyl group.
  • alkanolamines are selected from the group consisting of 2-aminoethane-1-ol (monoethanolamine), 3-aminopropan-1-ol, 4-aminobutan-1-ol, 5-aminopentan-1-ol, 1 Aminopropan-2-ol (monoisopropanolamine), 1-aminobutan-2-ol, 1-aminopentan-2-ol, 1-aminopentan-3-ol, 1-aminopentan-4-ol, 2-amino-2-methyl-propanol , 2-Amino-2-methylbutanol, 3-amino-2-methylpropan-1-ol, 1-amino-2-methylpropan-2-ol, 3-aminopropane-1,2-diol, 2-amino-2-methylpropane -1, 3-diol, 2-amino-2-ethyl-1, 3-propanediol, ⁇ , ⁇ -dimethyl-ethanolamine, tri
  • Very particularly preferred alkanolamines according to the invention are selected from the group of 2-aminoethane-1-ol (monoethanolamine), 2-amino-2-methyl-propan-1-ol, 2-amino-2-methyl-propane-1, 3 diol and triethanolamine.
  • Particularly preferred cosmetic agents (M1) contain monoethanolamine as the alkanolamine.
  • the at least one alkanolamine is in a total amount of 0.05 to 10 wt .-%, preferably from 0.5 to 6 wt .-%, in particular from 1 to 3 wt .-%, based on the total weight of the cosmetic composition.
  • organic alkalizing agents are selected from basic amino acids, more preferably selected from the group which is formed from L-arginine, D-arginine, D / L-arginine, L-lysine, D-lysine, D / L-lysine and Mixtures thereof.
  • Basic amino acids which are particularly preferred according to the invention are selected from L-arginine, D-arginine and D / L-arginine.
  • Preferred cosmetic agents (M1) contain at least one alkalizing agent other than alkanolamines and ammonia in a total amount of from 0.05 to 5% by weight, in particular from 0.5 to 3% by weight, based on the total weight of the cosmetic agent.
  • the cosmetic agents (M1) comprise a mixture of ammonia and at least one alkanolamine and optionally at least one further alkalizing agent other than alkanolamines and ammonia.
  • the pH of the cosmetic compositions (M1) measured at 22 ° C., is preferably 8 to 13, preferably 9.5 to 12, preferably 10 to 11.5, in particular 10.5 to 11.
  • the cosmetic agents (M1) are present in the form of a cream-shaped oil-in-water emulsion.
  • the oil-in-water emulsion cosmetic agents (M1) comprise at least one linear saturated alkanol having 12 to 30 carbon atoms, in particular 16 to 22 carbon atoms, in a total amount from 2 to 20 wt .-%, in particular from 5 to 15 wt .-%, based on the total weight of the cosmetic composition.
  • Cetyl alcohol, stearyl alcohol, arachidyl alcohol, behenyl alcohol and lanolin alcohol or mixtures of these alcohols, such as are obtainable in the industrial hydrogenation of vegetable and animal fatty acids, and mixtures of these alkanols are particularly suitable in the context of the present invention.
  • the mixture cetearyl alcohol particularly suitable in the context of the present invention.
  • the cosmetic compositions (M1) present as oil-in-water emulsion preferably comprise at least one partial ester of a polyol having 2 to 6 carbon atoms and linear saturated fatty acids having 12 to 30, in particular 14 to 22, carbon atoms, whereby the partial esters may be hydroxylated, in a total amount of 0.5 to 8 wt .-%, in particular from 3 to 6 wt .-%, based on the total weight of the cosmetic composition.
  • Such partial esters are in particular the mono- and diesters of glycerol or the monoesters of propylene glycol or the mono- or diesters of ethylene glycol or the mono-, di-, tri- and tetra-esters of pentaerythritol, each with linear saturated C 12 -C 20 -carboxylic acids which hydroxylates especially those with palmitic and stearic acid, the sorbitan mono-, di- or triesters of linear saturated C 12 -C 20 -carboxylic acids, which may be hydroxylated, in particular those of myristic acid, palmitic acid, stearic acid or of mixtures of these fatty acids and the methylglucose mono- and diesters of linear saturated C 12 -C 30 -carboxylic acids which may be hydroxylated.
  • the cosmetic agents (M1) present as oil-in-water emulsion to comprise at least one polyol partial ester selected from glycerol monostearate, glycerol monopalmitate, glyceryl distearate, glycerol dipalmitate, ethylene glycol monostearate, ethylene glycol monopalmitate, ethylene glycol distearate, ethylene glycol dipalmitate, and mixtures thereof, in particular mixtures of glycerol monostearate, glycerol monopalmitate, glycerol distearate and glycerol dipalmitate in a total amount of from 0.5 to 8% by weight, in particular from 3 to 6% by weight, based on the total weight of the cosmetic composition.
  • the cosmetic agents (M1) contain at least one surfactant.
  • Surfactants for the purposes of the present invention are amphiphilic (bifunctional) compounds which consist of at least one hydrophobic and at least one hydrophilic moiety.
  • the hydrophobic residue is preferably a hydrocarbon chain of 8 to 28 carbon atoms, which may be saturated or unsaturated, linear or branched. Most preferably, this Cs-C28 alkyl chain is linear.
  • the hydrophilic moiety is preferably a polyethylene oxide group having at least 2 EO units or an acid group.
  • a basic property of surfactants and emulsifiers is oriented adsorption at interfaces as well as aggregation into micelles and the formation of lyotropic phases.
  • the cosmetic agents (M1) present as oil-in-water emulsion therefore contain at least one ethoxylated nonionic surfactant in a total amount of from 0.5 to 6% by weight, in particular from 1 to 4% by weight, based on the total weight of the cosmetic product. It has proved to be particularly advantageous if the ethoxylated nonionic surfactant has an HLB value above 10, preferably above 13. For this purpose, it is necessary that the nonionic surfactant has a sufficiently high degree of ethoxylation.
  • the cosmetic agent (M1) therefore contains as ethoxylated nonionic surfactant at least one ethoxylated surfactant having at least 12 ethylene oxide units.
  • the addition products of 20 to 60 mol of ethylene oxide with castor oil and hydrogenated castor oil are particularly suitable according to the invention.
  • the at least one ethoxylated nonionic surfactant is preferably selected from surfactants having the INCI name ceteth-12, steareth-12, ceteareth-12, ceteth-20, steareth-20, ceteareth-20, ceteth-30, steareth-30, ceteareth- 30, Oleth-30, Ceteareth-50, PEG-40 Hydrogenated Castor Oil and PEG-60 Hydrogenated Castor Oil and mixtures thereof Substances, more preferably selected from ceteth-20, steareth-20, ceteareth-20, ceteth-30, steareth-30 and ceteareth-30.
  • the oil-in-water emulsion cosmetic compositions (M1) comprise at least one anionic surfactant in a total amount of 0.5 to 6 wt.%, In particular 1 to 4 wt. , based on the total weight of the cosmetic product.
  • anionic surfactants the following compounds are particularly preferred in the context of the present invention
  • Alkyl sulfates and alkyl polyglycol ether sulfates of the formula R-O (CH 2 -CH 2 O) x -OSO 3 H, in which R is a preferably linear alkyl group having 8 to 30 carbon atoms and x 0 or 1 to 12,
  • the cosmetic agents (M1) present as oil-in-water emulsion comprise at least one cationic or amphoteric polymer selected from the compounds having the INCI name "Polyquaternium” in a total amount of 0 , From 05 to 2% by weight, in particular from 0.1 to 0.5% by weight, based on the total weight of the cosmetic agent.
  • Polyquaternium-10, Polyquaternium-11, Polyquaternium-22, Polyquaternium-37 and Polyquaternium-39 most preferred are Polyquaternium-22, Polyquaternium-37 and Polyquaternium-39, Polyquaternium-39 is most preferred.
  • the cosmetic agents (M1) present as oil-in-water emulsion contain at least one polymeric thickener in a total amount of 0.05 to 2 Wt .-%, in particular from 0.1 to 1 wt .-%, based on the total weight of the cosmetic composition.
  • thickening agents have proved to be particularly advantageous which comprise at least one monomer of the acrylic or methacrylic acid type and derivatives thereof.
  • a polymer which is very particularly preferred according to the invention is a copolymer of two or more monomers selected from acrylic acid, methacrylic acid and their esters with C 1 -C 4 -alkyl groups.
  • a polymer which is very particularly preferred according to the invention is the copolymer known from the INCI name Acrylates Copolymer of two or more monomers selected from acrylic acid, methacrylic acid and their esters with C 1 -C 4 -alkyl groups.
  • Another very particularly preferred polymer according to the invention is carbomer, a cross-linked acrylic acid homopolymer.
  • Further very particularly preferred polymers according to the invention are methacrylic acid-free copolymers of acrylic acid and acrylic acid C 1 -C 4 esters.
  • the cosmetic agents (M1) present as oil-in-water emulsion comprise at least one polymeric thickener, selected from carbomer, in a total amount of from 0.05 to 2% by weight, in particular from 0.1 to 1 wt .-%, based on the total weight of cosmetic agent.
  • the cosmetic agents (M1) present as oil-in-water emulsion contain, based on the total weight of the cosmetic compositions,
  • Cetearyl alcohol in a total amount of 2 to 20 wt .-%, in particular from 5 to 15 wt .-%, further
  • At least one ethoxylated nonionic surfactant selected from ceteth-20, steareth-20, ceteareth-20, ceteth-30, steareth-30 and ceteareth-30, in a total amount of 0.5 to 6% by weight, in particular of 1 to 4 wt .-%, and
  • the packaging unit according to the invention contains, in addition to the cosmetic agent (M1) in the container (C1), at least one container (C2) with an oxidation preparation (M2).
  • the oxidizing agents contained in this oxidation preparation (M2) are in this case different from atmospheric oxygen.
  • Hydrogen peroxide and its solid addition products of organic and inorganic compounds are preferably used as the oxidizing agent.
  • Suitable solid addition products according to the invention are in particular the addition products of urea, melamine, polyvinylpyrrolidinone and sodium borate in question.
  • the at least one oxidizing agent is hydrogen peroxide and / or one of its solid addition products of organic or inorganic compounds.
  • a particularly preferred embodiment of the present invention is therefore characterized in that the oxidizing agent used is hydrogen peroxide in a total amount of from 7.2 to 20% by weight, preferably from 7.7 to 18% by weight, in particular from 8 to 15% by weight. %, in particular based on the total weight of the oxidizing agent preparation is included.
  • the calculation of the total amount refers to 100% H2O2.
  • the oxidizing agent preparations (M2) may further comprise water in a total amount of from 40 to 98% by weight, in particular from 70 to 91% by weight, based on the total weight of the oxidizing agent preparation.
  • the oxidizing agent preparations (M2) contain at least one linear saturated alkanol having 12 to 30 carbon atoms, in particular 16 to 22 carbon atoms in a total amount of 0.1 to 10 wt .-%, preferably from 0.5 to 5 wt .-%, in particular from 1 to 4 wt .-%, based on the total weight of the oxidizing agent preparation.
  • the mixture is cetearyl alcohol.
  • the oxidizing agent preparations (M2) comprise at least one ethoxylated nonionic surfactant, which is preferably selected from surfactants having the INCI name ceteth-12, steareth-12, ceteareth-12, ceteth-20, steareth-20 , Ceteareth-20, Ceteth-30, Steareth-30, Ceteareth-30, Oleth-30, Ceteareth-50, PEG-40 Hydrogenated Castor Oil and PEG-60 Hydrogenated Castor Oil and mixtures of these substances, most preferably selected from Ceteth-20 , Steareth-20, Ceteareth-20, Ceteth-30, Steareth-30 and Ceteareth-30 in a total amount of 0.1 to 10 wt .-%, preferably of 0.5 to 5 wt .-%, in particular from 1 to 4 wt .-%, based on the total weight of the oxidizing agent preparation.
  • ethoxylated nonionic surfactant which is preferably selected from surfactants having the INCI
  • the oxidizing agent preparations (M2) comprise at least one cationic surfactant in a total amount of 0.05 to 2% by weight, preferably of 0.1 to 1% by weight, in particular from 0.3 to 0.7% by weight, based on the total weight of the oxidizing agent preparation.
  • Preferred cationic surfactants have the formula (Tkat1 -1)
  • R 1, R 2, R 3 and R 4 each independently represent hydrogen, a methyl group, a phenyl group, a benzyl group or a saturated, branched or unbranched alkyl group having a chain length of 8 to 30 carbon atoms, which may optionally be substituted by one or more hydroxy groups.
  • A is a physiologically acceptable anion, for example halides such as chloride or bromide and methosulfates.
  • Examples of preferred compounds of the formula (Tkat1-1) are lauryltrimethylammonium chloride, cetyltrimethylammonium chloride, cetyltrimethylammonium bromide, cetyltrimethylammonium methosulfate, dicetyldimethylammonium chloride, tricetylmethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylbenzylammonium chloride, behenyltrimethylammonium chloride, behenyltrimethylammonium bromide and behenyltrimethylammonium methosulfate.
  • cationic surfactants have the formula (Tkat1 -2) on R2
  • radicals R1, R2 and R3 are each independently and may be the same or different.
  • the radicals R1, R2 and R3 mean:
  • branched or unbranched alkyl radical having 1 to 4 carbon atoms which may contain at least one hydroxyl group, or a saturated or unsaturated, branched or unbranched or cyclic saturated or unsaturated alkyl radical having from 6 to 30 carbon atoms which may contain at least one hydroxyl group, or
  • aryl or alkaryl radical for example phenyl or benzyl
  • n 1 to 200, preferably 1 to 100, preferably 1 to 50, in particular 1 to 20, with R 5 in the meaning of hydrogen, methyl or ethyl, or
  • hydroxyalkyl group of one to four carbon atoms which may be branched or unbranched, and which contains at least one and at most 3 hydroxy groups, such as -CHOH, -CHCH2OH, -CH2CHOH, -COHCHOH, -CHOHCOH, -CHCHOHCH3, -CH2COHCH3, -CH 2 CHOHCH 2 -, -C (CH 2 OH) 2, -CH 2 CHOHCH 2 OH, -CH 2 CH 2 CHOH, -CH 2 COHCH 3 and hydroxybutyl radicals, where the bond of -X- to R 4 is based on the free valence of the relevant carbon atom,
  • R6-0-CO- wherein R6 is a saturated or unsaturated, branched or unbranched or cyclic saturated or unsaturated alkyl radical having 6 to 30 carbon atoms, which may contain at least one hydroxy group, and which optionally further with 1 to 100 ethylene oxide units and / or 1 to 100 propylene oxide units can be ethoxylated, or
  • R 7-CO- in which R 7 is a saturated or unsaturated, branched or unbranched or cyclic saturated or unsaturated alkyl radical having 6 to 30 carbon atoms, which may contain at least one hydroxy group, and which may furthermore be admixed with 1 to 100 ethylene oxide units and / or or 1 to 100 propylene oxide units can be ethoxylated.
  • A is a physiologically acceptable organic or inorganic anion and is defined here as representative of all structures also described below.
  • the anion of all described cationic compounds is selected from the halide ions, fluoride, chloride, bromide, iodide, sulfates of the general formula RSO3 " , wherein R has the meaning of saturated or unsaturated alkyl radicals having 1 to 4 carbon atoms, or anionic radicals of organic acids such as maleate , Fumarate, oxalate, tartrate, citrate, lactate or acetate.
  • particularly preferred cationic surfactants of the formula (Tkatl - 2) contain the radical - (X - R 4) at least once to three times.
  • Such products are marketed under the trademarks Rewoquat ®, Stepantex® ®, Dehyquart® ®, ® and Armocare® Akypoquat ®.
  • Tkat1 -2) which are particularly preferred according to the invention include the formula (Tkat1-2.1), the cationic betaine esters.
  • R8 corresponds in its meaning to the previously defined radical R7.
  • esterquats with tradenames Armocare ® VGH-70 are, as well as Dehyquart ® F-75, Dehyquart ® L80, Stepantex ® VS 90 and Akypoquat ® 131st
  • the radicals R independently of one another each represent a saturated or unsaturated, linear or branched hydrocarbon radical having a chain length of 8 to 30 carbon atoms.
  • the preferred compounds of the formula (Tkat2) contain for R the same hydrocarbon radical.
  • the chain length of the radicals R is preferably 12 to 21 carbon atoms.
  • A is an anion as previously described. Examples according to the invention are obtainable, for example, under the INCI names Quaternium-27, Quaternium-72, Quaternium-83 and Quaternium-91. Quaternium-91 is particularly preferred according to the invention.
  • Another preferred cationic surfactant is an amidoamine and / or a cationized amidoamine having the following structural formula (Tkat3):
  • R 1 is an acyl or alkyl radical having 6 to 30 C atoms, which may be branched or unbranched, saturated or unsaturated, and wherein the acyl radical and / or the alkyl radical may contain at least one OH group, and R2, R3 and R4 are each independently
  • an alkyl radical having 1 to 4 carbon atoms which may be identical or different, saturated or unsaturated, or
  • hydroxyalkyl group having one to four carbon atoms having at least one and at most three hydroxy groups, for example -CH 2 OH, -CH 2 CH 2 OH, -CHOHCHOH, -CH 2 CHOHCH 3, -CH (CH 2 OH) 2, -COH (CH 2 OH) 2 , -CH 2 CHOHCH 2 OH, -CH 2 CH 2 CH 2 OH and hydroxybutyl radicals, and
  • A is an anion as previously described and
  • n is an integer between 1 and 10.
  • the alkylamidoamines can be present as such and converted by protonation in a correspondingly acidic solution into a quaternary compound.
  • the cationic alkylamidoamines are preferred. Examples of such used in this invention commercial products are Witcamine ® 100, Incromine ® BB, Mackine ® 401 and other Mackine ® grades, Adogen ® S18V, and as a permanent cationic aminoamines: Rewoquat ® RTM 50, Empigen ® CSC, Swanol ® Lanoquat DES-50 , Rewoquat ® UTM 50, Schercoquat® ® BAS ® Lexquat AMG-BEO, or Incroquat ® behenyl HE.
  • the oxidizing agent preparations (M2) contain, based on the total weight of the oxidizing agent preparations,
  • At least one ethoxylated nonionic surfactant which is preferably selected from surfactants having the INCI name ceteth-12, steareth-12, ceteareth-12, ceteth-20, steareth-20, ceteareth-20, ceteth-30, steareth-30, Ceteareth-30, Oleth-30, Ceteareth-50, PEG-40 Hydrogenated Castor Oil and PEG-60 Hydrogenated Castor Oil and mixtures of these substances, more preferably selected from Ceteth-20, Steareth-20, Ceteareth-20, Ceteth-30, Steareth-30 and ceteareth-30, in a total amount of 0.1 to 10 wt .-%, preferably from 0.5 to 5 wt .-%, in particular from 1 to 4 wt .-%, and
  • At least one cationic surfactant which is preferably selected from at least one cationic surfactant of the formula (Tkat1 -1), in a total amount of 0.05 to 2 wt .-%, preferably from 0.1 to 1 wt .-%, in particular from 0.3 to 0.7% by weight.
  • the oxidizing agent preparations (M2) of the packaging unit according to the invention also contain at least one acid.
  • Preferred acids are selected from dipicolinic acid, edible acids, such as, for example, citric acid, acetic acid, malic acid, lactic acid and tartaric acid, diluted mineral acids, such as hydrochloric acid, phosphoric acid and sulfuric acid, and mixtures thereof.
  • the oxidizing agent preparations (M2) preferably have a pH in the range from 2 to 5, in particular from 3 to 4, on.
  • the packaging unit contains at least one further hair treatment agent in an additional container, in particular a conditioner preparation or a bleaching powder with peroxodisulfates.
  • the conditioner composition advantageously contains at least one conditioning agent selected from the group of cationic polymers, silicone derivatives and oils.
  • the packaging unit application aids, such as combs, brushes, Applicetten or brush, personal protective clothing, especially disposable gloves, and optionally include instructions for use.
  • An applicette is understood to mean a broad brush, on whose end of the stem there is a tip, which allows and simplifies the division of fiber bundles out of the total amount of fibers.
  • a further subject of the present invention is a process for coloring keratinic fibers, which process comprises the following process steps:
  • step c) applying the mixture obtained in step c) to the keratinic fibers and leaving this mixture on the keratinic fibers for a time of 10 to 60 minutes, preferably from 20 to 45 minutes, at room temperature and / or at least 30 ° C,
  • the inventive method using the packaging unit according to the invention results in brightened keratinic fibers, which have a significantly improved combability and thus care.
  • the mixing of the cosmetic agent (M1) present in the packaging unit (kit-of-parts) with the oxidizing agent preparation (M2) in process step b) can be carried out either by mixing the cosmetic agent (M1) in the container (C1) with the oxidizing agent preparation ( M2) in the container (C2) or by mixing the oxidizing agent preparation (M2) in the container (C2) with the cosmetic agent (M1) in the container (C1).
  • Room temperature is to be understood in the context of the present invention, the ambient temperature.
  • the effect of the whitening preparation can be enhanced by external heat, for example by means of a heat hood.
  • the preferred exposure time of the whitening preparation to the keratinic fiber is 10 to 60 minutes, preferably 20 to 45 minutes.
  • the remaining lightening agent is washed out of the keratinic fibers by means of a cleaning preparation, which preferably contains at least one cationic and / or anionic and / or nonionic surfactant, and / or water. If necessary, the process is repeated with a further agent.
  • the keratinic fibers are optionally rinsed with an aftertreatment agent, such as a conditioner, and dried with a towel or a hot air blower.
  • an aftertreatment agent such as a conditioner
  • the application of the whitening preparation is usually done by hand by the user.
  • Personal protective clothing is preferably worn here, in particular suitable protective gloves, for example made of plastic or latex for single use (disposable gloves) and optionally an apron. But it is also possible to apply the brightening agent with an application aid on the keratinic fibers.
  • a further subject of the present invention is the use of the packaging unit according to the invention for increasing the care of keratinic fibers.
  • compositions of the cosmetic agents used oil-in-water emulsions, all amounts in% by weight.
  • the at least one cationic keratin hydrolyzate used in the following formulations preferably has one or more steardimonium hydroxypropyl group (s).
  • the fat base was melted together at 80 ° C and dispersed with a portion of the amount of water. Subsequently, the remaining recipe ingredients were incorporated with stirring in order. It was then made up to 100% by weight with water and the formulation was stirred cold.
  • the formulation V1 is a comparative formulation not according to the invention without cationized keratin hydrolyzate.
  • the formulations E1 and E2 are examples according to the invention.
  • Oxidizing agent preparation 01 (all amounts in% by weight) Raw material 01
  • Emulgade F (INCI name: Cetearyl alcohol, PEG-40 castor oil, sodium cetearyl sulfate, BASF) 2. Increasing the volume of dyed strands of hair
  • the cosmetic agents V1 and E1 and E2 were each mixed in a weight ratio of 1: 1 with the above oxidizing agent preparation 01.
  • each tress was moistened with combing with a hard rubber crest with fine teeth (Hercules shegemann, Hamburg Germany) for 2 seconds with water. After 3 combing operations have been performed, the combing force is measured during a further 10 combing operations, whereby the respective hair strand rotates slowly during the combing process. The resulting measurements are compared using the following statistical tests embedded in Statistica 10.0 software (StatSoft Inc., USA):
  • Ko is the average of the combing power for the undyed hair strands and Ki is the mean value for the hair strands treated with the respective oxidative coloring agent.
  • Table 1 shows the dK values for the colorations using the cosmetic agents V1, E1 and E2.
  • the colorations with the cosmetic compositions E1 and E2 according to the invention which comprise at least one cationic keratin hydrolyzate in a total amount of 0.5% by weight and 1.3% by weight, respectively, show, in comparison to a coloration without cationic keratin hydrolyzate (V1). a lower combing power and thus a significantly improved care.

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Abstract

La présente invention concerne une unité de vente (Kit), comprenant, dans des contenants distincts, un agent cosmétique (M1) contenant au moins un hydrolysat de kératine cationique, au moins un précurseur de colorant d'oxydation et au moins un agent basifiant, ainsi qu'une préparation d'agent d'oxydation (M2), l'utilisation du au moins un hydrolysat de kératine cationique entraînant l'amélioration du soin des fibres kératiniques. L'invention concerne également un procédé de coloration des fibres kératiniques à l'aide d'une unité de vente selon l'invention. La présente invention concerne enfin l'utilisation de l'unité de vente selon l'invention aux fins d'amélioration du soin des fibres kératiniques.
PCT/EP2015/058717 2014-06-05 2015-04-22 Agent éclaircissant à hydrolysats de kératine cationiques WO2015185264A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4369037A (en) * 1980-11-19 1983-01-18 Kao Soap Co., Ltd. Hair treatment cosmetics containing cationic keratin derivatives
US6312677B1 (en) * 1992-02-21 2001-11-06 L'oreal Cosmetic composition based on nonionic surfactants and cationic or amphoteric substantive polymers and its use as a dyeing or bleaching vehicle
WO2006108505A2 (fr) * 2005-04-12 2006-10-19 Henkel Kommanditgesellschaft Auf Aktien Colorants d'oxydation comprenant des derives de 2-furanone et de collagene
US20070256254A1 (en) * 2006-05-02 2007-11-08 L'oreal Conditioning cream color base having improved color deposition properties
US20090111750A1 (en) * 2007-10-31 2009-04-30 Keratec, Ltd. Keratin derivatives and methods of making the same
DE102012215968A1 (de) * 2012-09-10 2013-06-06 Henkel Ag & Co. Kgaa Stabilisierung künstlicher Haarfarben

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4369037A (en) * 1980-11-19 1983-01-18 Kao Soap Co., Ltd. Hair treatment cosmetics containing cationic keratin derivatives
US6312677B1 (en) * 1992-02-21 2001-11-06 L'oreal Cosmetic composition based on nonionic surfactants and cationic or amphoteric substantive polymers and its use as a dyeing or bleaching vehicle
WO2006108505A2 (fr) * 2005-04-12 2006-10-19 Henkel Kommanditgesellschaft Auf Aktien Colorants d'oxydation comprenant des derives de 2-furanone et de collagene
US20070256254A1 (en) * 2006-05-02 2007-11-08 L'oreal Conditioning cream color base having improved color deposition properties
US20090111750A1 (en) * 2007-10-31 2009-04-30 Keratec, Ltd. Keratin derivatives and methods of making the same
DE102012215968A1 (de) * 2012-09-10 2013-06-06 Henkel Ag & Co. Kgaa Stabilisierung künstlicher Haarfarben

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Title
COSM.TOIL., vol. 99, 1984, pages 63
F. AURICH ET AL., TENS.SURF.DET., vol. 29, 1992, pages 389
G. SCHUSTER; A. DOMSCH, SEIFEN ÖLE FETTE WACHSE, vol. 108, 1982, pages 177
H. W. STEISSLINGER, PARF.KOSM., vol. 72, 1991, pages 556

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