EP1150651A1 - Kosmetische zusammensetzungen enthaltend mindestens eine wachse und mindestens eine ceramideverbindung sowie das verfahren - Google Patents

Kosmetische zusammensetzungen enthaltend mindestens eine wachse und mindestens eine ceramideverbindung sowie das verfahren

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Publication number
EP1150651A1
EP1150651A1 EP00900630A EP00900630A EP1150651A1 EP 1150651 A1 EP1150651 A1 EP 1150651A1 EP 00900630 A EP00900630 A EP 00900630A EP 00900630 A EP00900630 A EP 00900630A EP 1150651 A1 EP1150651 A1 EP 1150651A1
Authority
EP
European Patent Office
Prior art keywords
radical
composition
composition according
denotes
weight
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP00900630A
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English (en)
French (fr)
Inventor
Serge Restle
Danièle Cauwet-Martin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by LOreal SA filed Critical LOreal SA
Publication of EP1150651A1 publication Critical patent/EP1150651A1/de
Withdrawn legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/68Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair

Definitions

  • the present invention relates to a cosmetic composition for the treatment of eratin materials such as the hair, comprising at least one particular wax and at least one compound of ceramide type as well as to the non-therapeutic treatment process using this composition.
  • Ceramides or glycoceramides are also known which have already been combined with cholesterol esters in order to protect the hair fiber.
  • the hair is damaged by the heat of the blow dryer and the passage of the brush through the hair to shape the hair.
  • compositions containing a particular wax in combination with compounds of Ceramide type a significant improvement in cosmetic performance was observed both on wet hair and on dry hair.
  • the Applicant has found in particular that the combination has a synergistic effect which is not simply the addition of the properties of the two components.
  • the disentangling properties are also superior to those of a composition containing only the compound of ceramide type or that wax.
  • the subject of the invention is therefore a cosmetic composition intended for the treatment of keratin materials, in particular the hair, characterized in that it contains in a cosmetically acceptable medium at least one wax having a melting point of between 70 and 85 °. C and of which at least 80% of the carbon chains have more than 40 carbon atoms and at least one compound of the ceramide type.
  • compositions defined above to protect keratin materials, in particular the hair, from physical or chemical attack and in particular with regard to brushing.
  • compositions also make it possible to improve the cosmetic properties, in particular the softness and straightening of the hair.
  • ceramide-type compound means ceramides and / or glycoceramides and / or pseudoceramides and / or neoceramides, natural or synthetic. Ceramide-type compounds are described for example in patent applications DE4424530, DE4424533, DE4402929, DE4420736, WO95 / 23807, WO94 / 07844, EP-A-0646572, WO95 / 16665, FR-2 673 179, EP-A- 0227994 and WO 94/07844, WO94 / 24097, WO94 / 10131, the teachings of which are included here for reference.
  • ceramide-type compounds which can be used according to the present invention preferably correspond to the general formula (I):
  • R7 being a radical hydrocarbon, saturated or unsaturated, linear or branched, optionally mono or polyhydroxylated, in C1-C35, the hydroxyl or hydroxyls of the radical R7 can be esterified with a saturated or unsaturated fatty acid, linear or branched, optionally mono or polyhydroxylated, in C- 1-C35; - or a radical R "- (NR-CO) -R ', R denotes a hydrogen atom or a hydrocarbon radical C1-C20 mono or polyhydroxylated, preferably monohydroxylated, R' and R" are hydrocarbon radicals whose sum of carbon atoms is between 9 and 30, R 'being a divalent radical.
  • R denotes a hydrocarbon radical in C-1-C20 P t are an integer ranging from 1 to 12.
  • R2 is chosen from a hydrogen atom, a saccharide-type radical, in particular a (glycosyl) n , (galactosyl) m or sulfogalactosyl radical, a sulfate or phosphate residue, a phosphorylethylamine radical and a radical phosphorylethylammonium, in which n is an integer varying from 1 to 4 and m is an integer varying from 1 to 8;
  • R3 denotes a hydrogen atom or a C-1-C33 hydrocarbon radical, saturated or unsaturated, hydroxyl or not, the hydroxyl or hydroxyls which can be esterified by a mineral acid or an acid R7COOH, R7 having the same meanings as ci above, the hydroxyl or hydroxyls which can be etherified by a (glycosyl) n , (galactosyl) m sulfogalactosyl, phosphorylethylamine or phosphorylethylammonium radical, R3 can also be substituted by one or more C alk alkyl radicals
  • R4 denotes a hydrogen atom, a methyl, ethyl radical, a C3-C5Q hydrocarbon radical, saturated or unsaturated, linear or branched, optionally hydroxyl or a -CH2-CHOH-CH2-O-R5 radical in which R ⁇ denotes a C ⁇ n-C-26 hydrocarbon radical or a rad ' ca ' R8-0-CO- (CH2) p , Rg denotes a C ⁇ -C20 hydrocarbon radical > P is an integer varying from 1 to 12,
  • R5 denotes a hydrogen atom or a saturated or unsaturated, linear or branched C-1-C30 hydrocarbon radical, optionally mono or polyhydroxylated, the hydroxyl (s) possibly being etherified by a (glycosyl) n , (galactosyl) radical m ] sulfogalactosyl, phosphorylethylamine or phosphorylethylammonium,
  • R3 and R5 denote hydrogen or when R3 denotes hydrogen and R5 denotes methyl then R4 does not denote a hydrogen atom, a methyl or ethyl radical.
  • ceramides and / or glycoceramides are preferred, the structure of which is described by DOWNING in Journal of Lipid Research Vol. 35, 2060-2068, 1994, or those described in French patent application FR-2 673 179, the teachings of which are included here for reference.
  • the compounds of ceramide type more particularly preferred according to the invention are the compounds of formula (I) for which R- j denotes a saturated or unsaturated alkyl derived from C14-C22 fatty acids optionally hydroxylated; R2 denotes a hydrogen atom; and R3 denotes a linear radical in C-) 1.-17 optionally hydroxyl and preferably in Ci 3. 5.
  • Such compounds are for example:
  • R denotes a saturated or unsaturated alkyl radical derived from C 2 -C 22 fatty acids
  • R2 denotes a galactosyl or sulfogalactosyl radical
  • the concentration of ceramide-type compounds can vary between 0.0001% and 20% by weight approximately relative to the total weight of the composition, and preferably between 0.001 and 10% approximately and even more preferably between 0.005 and 3% by weight.
  • the waxes which can be used according to the invention preferably have at least 80% by weight of carbon chains comprising from 40 to 65 carbon atoms and preferably more than 95% by weight.
  • Waxes meeting these characteristics are in particular sunflower wax, in particular hydrogenated sunflower wax sold by the Soetenaey Laboratory, the melting point of which is approximately 77 ° C. (measured in the KOFLER block), the drop point is d 'about 70 ° C and which contains more than 95% by weight of carbon chains having 40 to 65 carbon atoms.
  • the wax concentration according to the invention can vary between 0.0001% and 20% by weight approximately relative to the total weight of the composition, and preferably between 0.001 and 10% approximately and even more preferably between 0.005 and 3% by weight .
  • compositions of the invention also advantageously contain at least one surfactant which is generally present in an amount of between 0.1% and 60% by weight approximately, preferably between 3% and 40% and even more preferably between 5% and 30%, relative to the total weight of the composition.
  • This surfactant can be chosen from anionic, amphoteric, nonionic, cationic surfactants or mixtures thereof.
  • the surfactants which are suitable for carrying out the present invention are in particular the following:
  • Anionic surfactant (s): Their nature is not, in the context of the present invention, of a truly critical nature.
  • anionic surfactants which can be used, alone or in mixtures, in the context of the present invention, mention may be made in particular (non-limiting list) of the salts (in particular alkali salts, in particular sodium salts, ammonium salts, amine salts, amino alcohol salts or magnesium salts) of the following compounds: alkylsulphates, alkylethersulphates, alkylamidoethersulphates, alkylarylpolyethersulphates, monoglycerides sulphates; alkylsulfonates, alkylphosphates, alkylamidesulfonates, alkylarylsulfonates, ⁇ -olefin-sulfonates, paraffin-sulfonates; alkylsulfosuccinates, alkylethersulfosuccinates, alkylamidesulfosuccinates; alkyl sulfosuccinamates; alkyl sulfoacetate
  • anionic surfactants which can still be used, mention may also be made of the salts of fatty acids such as the salts of oleic, ricinoleic, palmitic, stearic acids, coconut oil or hydrogenated coconut oil acids; acyl-lactylates whose acyl radical contains 8 to 20 carbon atoms.
  • Weakly anionic surfactants can also be used, such as alkyl D galactoside uronic acids and their salts as well as polyoxyalkylenated (C 6 -C 2 ) alkyl ether acids, (C 6 -C 24 ) aryl ether carboxylic acids. polyoxyalkylenated, (C 6 -C 24 ) alkyl amido ether polyoxyalkylenated carboxylic acids and their salts, in particular those comprising from 2 to 50 ethylene oxide groups, and mixtures thereof.
  • anionic surfactants it is preferred to use, according to the invention, the salts of alkyl sulfates and of alkyl ether sulfates and their mixtures.
  • Nonionic surfactant (ii) Nonionic surfactant (s):
  • the nonionic surfactants are also compounds well known per se (see in particular in this regard "Handbook of Surfactants” by MR PORTER, Blackie & Son editions (Glasgow and London), 1991, pp 116-178) and their nature is not, in the context of the present invention, of a critical nature.
  • alcohols can in particular be chosen from (nonlimiting list) alcohols, alpha-diols, alkylphenols or polyethoxylated, polypropoxylated or polyglycerolated fatty acids, having a fatty chain comprising for example 8 to 18 carbon atoms, the number of ethylene oxide or propylene oxide groups which may range in particular from 2 to 50 and the number of glycerol groups which may range in particular from 2 to 30.
  • copolymers of ethylene oxide and of propylene, condensates of ethylene and propylene oxide on fatty alcohols polyethoxylated fatty amides preferably having from 2 to 30 moles of ethylene oxide, polyglycerolated fatty amides comprising on average 1 to 5 glycerol groups and in particular 1, 5 to 4; polyethoxylated fatty amines preferably having 2 to 30 moles of ethylene oxide; esters of oxyethylenated sorbitan fatty acids having from 2 to 30 moles of ethylene oxide; sucrose fatty acid esters, polyethylene glycol fatty acid esters, alkylpolyglycosides, N-alkyl glucamine derivatives, amine oxides such as amino (CQ - C 4) alkyl oxides or N-acylaminopropylmorpholine oxides.
  • the alkylpolyglycosides constitute nonionic surfactants which fall particularly well within
  • amphoteric surfactant (s) can in particular be (non-limiting list) derivatives of secondary or tertiary amines aliphatics, in which the aliphatic radical is a linear or branched chain containing 8 to 22 carbon atoms and containing at least one water-soluble anionic group (for example carboxylate, sulfonate, sulfate, phosphate or phosphonate); mention may also be made of (C 8 -C 20 ) alkyl betaines, sulfobetaines, (C 8 -C 20 ) alkyl amidoalkyl (C, -C 6 ) betaines or (C 8 -C 20 ) alkyl amidoalkyl (CC 6) ) sulfobetaines.
  • aliphatic radical is a linear or branched chain containing 8 to 22 carbon atoms and containing at least one water-soluble anionic group (for example carboxylate, sulfonate, sulf
  • B represents -CH 2 CH 2 OX '
  • C represents - (CH 2 ) Z -Y
  • z 1 or 2
  • X' denotes the group -CH 2 CH 2 -COOH or a hydrogen atom
  • Y denotes -COOH or the radical -CH 2 - CHOH - SO3H
  • R 5 denotes an alkyl radical of an acid R 9 -COOH present in coconut oil or in hydrolyzed linseed oil, an alkyl radical, in particular C 7 , C 9 , C fatigueor C 13 , a C 17 alkyl radical and its iso form, an unsaturated C 17 radical.
  • Cocoamphodipropionic acid By way of example, mention may be made of the cocoamphodiacetate sold under the trade name MIRANOL C2M concentrated by the company RHONE
  • compositions in accordance with the invention mixtures of surfactants and in particular mixtures of anionic surfactants and mixtures of anionic surfactants and amphoteric or nonionic surfactants are preferably used.
  • a particularly preferred mixture is a mixture consisting of at least one anionic surfactant and at least one amphoteric surfactant.
  • an anionic surfactant is used selected from alkyl (C 12 -C 14) alkyl sulphates of sodium, triethanolamine or ammonium alkyl (C 12 -C 14) alkyl ether sulfates of sodium, triethanolamine or ammonium oxyethylenated with 2.2 moles of ethylene oxide, sodium cocoyl isethionate and alphaolefin (C 14 -C ⁇ 6 ) sodium sulfonate and their mixture with: - or an amphoteric surfactant such as the amine derivatives called disodiumcocoamphodipropionate or sodiumcocoamphopropionate sold in particular by the company RHONE POULENC under the trade name "MIF ANOL C2M CONC" in aqueous solution at 38% of active material or under the name MIRANOL C32;
  • amphoteric surfactant of zwitterionic type such as alkylbetaines in particular cocobetaine sold under the name "DEHYTON AB 30" in aqueous solution at 32% of MA by the company HENKEL.
  • cationic surfactants among which there may be mentioned in particular (non-limiting list): the salts of primary, secondary or tertiary fatty amines, possibly polyoxyalkylenated; quaternary ammonium salts such as chlorides or bromides of tetraalkylammonium, alkylamidoalkyltrialkylammoniurn, trialkylbenzylammonium, trialkylhydroxyalkylammonium or alkylpyridinium; imidazoline derivatives; or amine oxides of a cationic nature.
  • quaternary ammonium salts such as chlorides or bromides of tetraalkylammonium, alkylamidoalkyltrialkylammoniurn, trialkylbenzylammonium, trialkylhydroxyalkylammonium or alkylpyridinium
  • imidazoline derivatives or amine oxides of a cationic nature.
  • composition of the invention may also contain at least one additive chosen from thickeners, perfumes, pearlescent agents, preservatives, sun filters, anionic or nonionic or cationic or amphoteric polymers, proteins, protein hydrolysates. , fatty acids with linear or branched C 1S -C 40 chains such as 18-methyl eicosanoic acid, hydroxy acids, vitamins, panthenol, vegetable, animal, mineral or synthetic oils and any other additive conventionally used in the cosmetic field which does not affect the properties of the compositions according to the invention.
  • additives are present in the composition according to the invention in proportions which can range from 0 to 50% by weight relative to the total weight of the composition.
  • the precise quantity of each additive is easily determined by the skilled person according to its nature and its function.
  • the cosmetically acceptable medium can consist solely of water or of a mixture of water and at least one cosmetically acceptable solvent such as monoalcohols, polyalcohols, glycol ethers and their mixture.
  • Monoalcohols are in particular chosen from CC 4 lower alcohols, such as ethanol, isopropanol, tert-butanol, n-butanol; alkylene glycols such as propylene glycol, glycol ethers and their mixture.
  • the composition comprises from 50 to 95% by weight of water relative to the total weight of the composition.
  • the pH of the compositions is generally between 2 and 12 and preferably between 4 and 9.
  • the adjustment of the pH to the desired value can be carried out conventionally by adding a base (organic or inorganic) in the composition, for example of ammonia or a primary, secondary or tertiary (poly) amine such as monoethanolamine, diethanolamine, triethanolamine, isopropanolamine or propane-1, 3, or alternatively by addition of a mineral or organic acid, preferably a carboxylic acid such as for example citric acid.
  • a base organic or inorganic
  • a primary, secondary or tertiary (poly) amine such as monoethanolamine, diethanolamine, triethanolamine, isopropanolamine or propane-1, 3, or alternatively by addition of a mineral or organic acid, preferably a carboxylic acid such as for example citric acid.
  • compositions according to the invention can be more particularly used for washing or treating keratin materials such as the hair, the skin, the eyelashes, the eyebrows, the nails, the lips, the scalp and more particularly the hair.
  • compositions according to the invention are detergent compositions such as shampoos, shower gels and bubble baths.
  • the compositions comprise a washing base, generally aqueous.
  • the surfactant (s) forming the washing base can be chosen either, alone or as a mixture, from anionic, amphoteric, nonionic and cationic surfactants as defined above.
  • the quantity and quality of the washing base are those sufficient to give the final composition a satisfactory foaming and / or detergent power.
  • the washing base can represent from 4% to 50% by weight, preferably from 6% to 35% by weight, and even more preferably from 8% to 25% by weight, of the total weight of the final composition.
  • the subject of the invention is also a process for treating keratin materials such as the skin or the hair, characterized in that it consists in applying to the keratin materials a cosmetic composition as defined above, then in optionally rinsing with the water.
  • this method according to the invention allows the hairstyle to be maintained, the treatment, the care or the washing or the make-up removal of the skin, the hair or any other keratin material.
  • compositions of the invention can also be in the form of conditioner to rinse off or not, of compositions for perm, straightening, coloring or discoloration, or also in the form of compositions to rinse, to be applied before or after coloring, discoloration, perm or straightening or between the two stages of a perm or straightening.
  • compositions according to the invention can be used as leave-in products, in particular for maintaining the hairstyle, shaping or styling the hair.
  • They are more particularly styling lotions, brushing lotions, fixing compositions (lacquers) and styling.
  • compositions of the invention may also be in the form of washing compositions for the skin, and in particular in the form of solutions or gels for the bath or shower or of make-up removing products.
  • compositions according to the invention can also be in the form of aqueous or hydroalcoholic lotions for the care of the skin and / or the hair.
  • the cosmetic compositions according to the invention can be in the form of a gel, milk, cream, lotion, stick, emulsion, thickened lotion or foam and can be used for the skin, nails, eyelashes, the lips and more particularly the hair.
  • compositions can be packaged in various forms, in particular in vaporizers, pump-dispenser bottles or in aerosol containers in order to ensure application of the composition in vaporized form or in the form of foam.
  • forms of packaging are indicated, for example, when it is desired to obtain a spray, a lacquer or a foam for the treatment of hair.
  • composition according to the invention when packaged in the form of an aerosol in order to obtain an aerosol lacquer or foam, it comprises at least one propellant which can be chosen from volatile hydrocarbons such as n-butane, propane , isobutane, pentane, a chlorinated and / or fluorinated hydrocarbon and their mixtures. Carbon dioxide, nitrous oxide, dimethyl ether, nitrogen, compressed air and mixtures thereof can also be used as the propellant.
  • propellant can be chosen from volatile hydrocarbons such as n-butane, propane , isobutane, pentane, a chlorinated and / or fluorinated hydrocarbon and their mixtures.
  • Carbon dioxide, nitrous oxide, dimethyl ether, nitrogen, compressed air and mixtures thereof can also be used as the propellant.
  • MA means active material
  • composition 1 g is applied to locks (2.7 g) of hair previously washed and towel-dried. Leave to stand for 5 minutes, comb the locks and then rinse them with water.
  • a movable wick, fixed on a sliding bench, is driven in a horizontal rectilinear movement between two other fixed wicks.
  • the force to be applied to slide the wick is measured using an electronic gauge connected to the drive arm. The lower the sliding force, the better the cosmetic properties.
  • composition 1 according to the invention is much lower than that of compositions 2,3 and 4.
  • the composition containing both ceramide and sunflower wax therefore has better cosmetic properties than those containing only one of the two compounds.
  • composition 1 g is applied to locks (2.7 g) of hair previously washed and towel-dried. Leave to stand for 5 minutes, comb the locks and then rinse them with water.
  • Brushing is carried out using a brush and a hair dryer. Brushing is carried out by passing the brush from root to tip. Broken hair is carefully collected on the brush using a comb, then it is weighed. The mass of hair recovered for a lock is reduced to the mass of hair recovered for one gram of starting hair.
  • the mass of hair recovered was compared for each of the compositions 1 to 4. The higher the mass of broken hair, the less the composition protects the hair.
  • the following shampoo composition was prepared:
  • Cocoyl betaine at 30% MA 2.5 g MA
  • Hair treated with this composition has very good cosmetic properties.
  • a rinse-off conditioner of the following composition was prepared
  • Cetylstearyl alcohol (50/50 by weight) 5 g Mixture of myristate, palmitate, myristyl stearate, cetyl and stearyl 1 g
  • a rinse-off conditioner of the following composition was prepared
  • a rinse-off conditioner of the following composition was prepared Cetylstearyl alcohol (50/50 by weight) 6 g
EP00900630A 1999-01-27 2000-01-20 Kosmetische zusammensetzungen enthaltend mindestens eine wachse und mindestens eine ceramideverbindung sowie das verfahren Withdrawn EP1150651A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9900883A FR2788689B1 (fr) 1999-01-27 1999-01-27 Composition cosmetique comprenant au moins une cire et au moins un compose de type ceramide et procedes
FR9900883 1999-01-27
PCT/FR2000/000128 WO2000044345A1 (fr) 1999-01-27 2000-01-20 Composition cosmetique comprenant au moins une cire et au moins un compose de type ceramide et procedes

Publications (1)

Publication Number Publication Date
EP1150651A1 true EP1150651A1 (de) 2001-11-07

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EP00900630A Withdrawn EP1150651A1 (de) 1999-01-27 2000-01-20 Kosmetische zusammensetzungen enthaltend mindestens eine wachse und mindestens eine ceramideverbindung sowie das verfahren

Country Status (10)

Country Link
EP (1) EP1150651A1 (de)
JP (1) JP2003500337A (de)
KR (1) KR20010089623A (de)
CN (1) CN1338921A (de)
AU (1) AU3057300A (de)
BR (1) BR0009137A (de)
CA (1) CA2360639A1 (de)
FR (1) FR2788689B1 (de)
PL (1) PL350299A1 (de)
WO (1) WO2000044345A1 (de)

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CN115947666A (zh) * 2023-02-02 2023-04-11 深圳市迪克曼生物科技有限公司 米糠油神经酰胺及其合成方法与用途

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CN100438852C (zh) 2002-12-25 2008-12-03 花王株式会社 毛发清洁剂
JP3779679B2 (ja) 2002-12-25 2006-05-31 花王株式会社 毛髪洗浄剤
FR2850579B1 (fr) * 2003-02-03 2006-08-18 Oreal Utilisation de mono-ou di-esters d'acide cinnamique ou de l'un de ses derives et de vitamine c, comme donneur de no
CA2456031A1 (fr) * 2003-02-03 2004-08-03 L'oreal Utilisation de mono- ou di-esters d'acide cinnamique ou de l'un de ses derives et de vitamine c, comme donneur de no
JP4220824B2 (ja) 2003-04-17 2009-02-04 花王株式会社 毛髪洗浄剤
GB2416303A (en) * 2004-07-14 2006-01-25 Mercy Ege After relaxer hair cream
KR100837558B1 (ko) * 2007-04-30 2008-06-12 (주)아모레퍼시픽 이중으로 안정된 세라마이드 나노 캡슐 포함 에멀젼조성물, 그의 제조방법 및 이를 이용한 피부 화장료 조성물
CN104840373A (zh) * 2015-04-28 2015-08-19 苏州药基美研医药科技有限公司 一种用于缓解干燥性嘴唇的护理品
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Publication number Priority date Publication date Assignee Title
CN115947666A (zh) * 2023-02-02 2023-04-11 深圳市迪克曼生物科技有限公司 米糠油神经酰胺及其合成方法与用途

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JP2003500337A (ja) 2003-01-07
CN1338921A (zh) 2002-03-06
PL350299A1 (en) 2002-12-02
WO2000044345A1 (fr) 2000-08-03
FR2788689A1 (fr) 2000-07-28
KR20010089623A (ko) 2001-10-06
FR2788689B1 (fr) 2002-06-07
AU3057300A (en) 2000-08-18
CA2360639A1 (fr) 2000-08-03
BR0009137A (pt) 2002-02-26

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