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EP3082749A1 - Produit cosmétique nettoyant doux - Google Patents

Produit cosmétique nettoyant doux

Info

Publication number
EP3082749A1
EP3082749A1 EP14806666.5A EP14806666A EP3082749A1 EP 3082749 A1 EP3082749 A1 EP 3082749A1 EP 14806666 A EP14806666 A EP 14806666A EP 3082749 A1 EP3082749 A1 EP 3082749A1
Authority
EP
European Patent Office
Prior art keywords
weight
radical
formula
cleaning agent
agent according
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Withdrawn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
EP14806666.5A
Other languages
German (de)
English (en)
Inventor
Thomas Schröder
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP3082749A1 publication Critical patent/EP3082749A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A61K8/46—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
    • A61K8/40—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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/007—Preparations for dry skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/596—Mixtures of surface active compounds

Definitions

  • the invention is in the field of cosmetics and relates to mild detergents containing a special surfactant mixture.
  • Cosmetic cleaners such as hair shampoos, are based on classical anionic, amphoteric, zwitterionic, nonionic and / or cationic surfactants.
  • Typical anionic surfactants used in a variety of commercially available shampoos are alkyl sulfates or alkyl ether sulfates.
  • Alkyl ether sulfates are usually preferred because they are milder and have excellent foaming power.
  • alkyl ether sulfates are not always satisfactory, as they may be useful for these applications have high irritation potential and give damaged hair an increased brittleness.
  • surfactant mixtures which have sufficiently high foam quantities and qualities and which cause no or only a slight irritation potential on the skin and / or the mucous membrane.
  • the surfactant mixtures should also be suitable for use in hair-treatment compositions, especially for use in hair-cleansing preparations having good care properties.
  • the application WO 92/084440 discloses mild surfactant blends having excellent foaming properties containing a mixture of acyl isethionates, zwitterionic surfactants and alkyl ether sulfates.
  • WO11 / 015857 discloses skin low irritation cleaning compositions containing novel Cs so-alkoyl alkyl isethionates and amphoteric surfactants in a weight ratio of 4: 1 to 1: 4.
  • the mild detergents are suitable for use as a baby shampoo.
  • a disadvantage of a variety of mild skin and hair cleansers is that their better skin compatibility is often at the expense of the texture of the detergents.
  • Another disadvantage is the often unsatisfactory foam quantities and properties that can be achieved with mild hair cleansers.
  • the present invention therefore an object of the invention to produce very mild cosmetic cleanser, which are well tolerated by the skin and mucosa.
  • the detergents should have a user-friendly texture and produce high amounts of foam when combined with water. Furthermore, the cleaning agents should have improved care properties.
  • a first subject of the invention is a cosmetic cleanser which is in a suitable carrier
  • At least one of the radicals R 2 to R 5 is a C 1 -C 4 -alkyl radical, and the other radicals independently of one another represent a hydrogen atom or a C 1 -C 4 -alkyl radical,
  • Each R is a linear or branched, saturated or unsaturated alkyl radical having 6 to 30 carbon atoms
  • M + is in each case an ammonium, an alkanolammonium or a metal cation, b) at least one second anionic surfactant of the following formula (II),
  • R ' is a linear or branched, saturated or unsaturated alkyl radical having 6 to 30 carbon atoms
  • n is a number from 0 to 20, preferably from 1 to 10
  • X is an ammonium, an alkanolammonium or a metal cation, and c) at least one C2-C4 mono- and / or dialkanolamide of at least one C8-C24 - Contains carboxylic acid.
  • a suitable carrier is preferably understood as meaning an aqueous or aqueous-alcoholic carrier.
  • the carrier contains at least 50% by weight, more preferably at least 60% by weight, and most preferably at least 70% by weight of water.
  • the cosmetic carrier may contain from 0.01 to 40% by weight, preferably from 0.05 to 35% by weight and in particular from 0.1 to 30% by weight, of at least one alcohol which may be selected from ethanol, Propanol, 2-propanol, isopropanol, glycerol, diglycerol, triglycerol, 1-butanol, 2-butanol, 1, 2-butanediol, 1, 3-butanediol, 1-pentanol, 2-pentanol, 1, 2-pentanediol, 1, 5-pentanediol, 1, hexanol, 2-hexanol, 1, 2-hexanediol, 1, 6-hexanediol, polyethylene glycols, sorbitol, sorbitan, benzyl alcohol, phenoxyethanol or mixtures of these alcohols.
  • at least one alcohol which may be selected from ethanol, Propanol, 2-propanol, isopropanol
  • ethanol particularly preferred are ethanol, 1-propanol, 2-propanol, isopropanol, 1, 2-propylene glycol, glycerol, benzyl alcohol and / or phenoxyethanol and mixtures of these alcohols.
  • glycerin particularly preferred is glycerin.
  • Preferred anionic surfactants of the abovementioned formula (I) have, as radical R, a linear or branched, saturated or unsaturated alkyl radical having 8 to 18 carbon atoms.
  • the radical R is a Cs, Oo, C12, C14, Ci6 radical or mixtures of these fatty acid radicals, as are obtained when the fatty acid (s) is derived from natural oils such as coconut oil (s) ,
  • radicals R 2 to R 5 may each stand for hydrogen or a methyl, ethyl, n-propyl, n-butyl or 2-butyl group.
  • the radicals R 2 to R 5 are preferably hydrogen or at least one of the radicals R 2 to R 5 is a methyl, ethyl or n-propyl group and in particular a methyl group.
  • one of the radicals R 2 to R 5 is a C 1 -C 4 radical
  • Alkyl group - especially a methyl group - and the other radicals each for a
  • the anionic surfactant of the formula (I) contains an isomer mixture in which both components are present, for example, as the radical R 2 is a C 1 -C 4 alkyl group - especially a methyl group - and as radicals R 3 to R 5 each have a hydrogen atom, as well as components which, for example, as the radical R 5, a C1-C4 alkyl group - in particular a methyl group - and as radicals R 2 to R 4 each have a hydrogen atom.
  • M + in the aforementioned formula (I) is preferably an alkali metal cation or an ammonium ion. Most preferably, the M + is a potassium or a sodium ion and most preferably a sodium ion.
  • Particularly preferred anionic surfactants according to the aforementioned formula (I) are those under the INCI names Sodium Cocoyl Isethionate, Sodium Lauroyl Isethionate, Sodium Myristyl Isethionate, Sodium Palmitoyl Isethionate, Sodium Stearyl Isethionate, Sodium Oleyl Isethionate, Sodium Cocoyl Methyl Isethionate, Sodium Lauroyl Methyl Isethionate, Sodium Myristyl Methyl Isethionate, Sodium Palmitoyl Methyl Isethionate, Sodium Stearyl Methyl Isethionate and / or Sodium Oleyl Methyl Isethionate.
  • Preferred anionic surfactants of the abovementioned formula (II) have, as the radical R ', preferably a linear or branched, saturated or unsaturated alkyl radical having 8 to 18 carbon atoms. Particularly preferably, the radical R 'is a Cs, C10, C12, C14, Ci6 radical or mixtures of these fatty acid radicals as obtained when the fatty acid (s) is derived from natural oils such as coconut oil (n ).
  • n is particularly preferably 0 or the numbers 1, 2, 3, 4, 5, 6, 7 or 8.
  • X in the aforementioned formula (IV) is preferably an alkali metal or an ammonium ion.
  • the X is a potassium or a sodium ion and particularly preferably a sodium ion.
  • Very particularly preferred anionic surfactants of the formula (II) are, for example, the compounds known under the INCI names Disodium Lauryl Sulfosuccinate, Disodium Laureth Sulfosuccinate and Disodium Cocoyl Sulfosuccinate.
  • disodium laureth sulfosuccinate is Especially preferred.
  • C 2 -C 4 -mono- and / or dialkanolamides of at least one C 8 -C 24 -carboxylic acid are preferably understood as meaning the ethanol and / or isopropanolamides of Cs-C 24 -carboxylic acids, the representatives being those derived from coconut fatty acids, lauric acid, myristic acid , Palmitic acid and stearic acid are particularly preferred.
  • C2-C4 mono- and / or dialkanolamides are designated according to the INCI nomenclature as Cocamide MEA, Cocamide DEA, Cocamide MIPA, Lauramide MEA, Lauramide DEA, Lauramide MIPA, Palmitoylamide MEA, Palmitoylamide DEA, Stearamide MEA and Stearamide DEA ,
  • cosmetic cleansing compositions according to the invention are characterized in that they are known under the INCI names Cocamide MEA, Cocamide MIPA and / or Lauramide MEA.
  • cosmetic cleansing compositions according to the invention are characterized in that they are known under the INCI names Cocamide MEA, Cocamide MIPA and / or Lauramide MEA.
  • R 2 to R 5 is a methyl radical and the other radicals are a hydrogen atom
  • R is a linear or branched, saturated or unsaturated alkyl radical having 8 to 18 carbon atoms
  • M + is a sodium, potassium or ammonium ion.
  • R ' is a linear, saturated alkyl radical having 8 to 18 carbon atoms, n is a number from 1 to 8, and
  • X is a sodium, potassium or ammonium ion
  • c) contain at least one monoethanolamide of a Cs-Os carboxylic acid.
  • cosmetic cleansing compositions which are a) at least one of the anionic surfactants known under the INCI names sodium lauroyl methyl isethionate or sodium cocoyl methyl isethionate,
  • c) contains at least one of the known under the INCI name Cocamide MEA, Cocamide MIPA or Lauramide MEA compound.
  • the surfactants a), b) and c) are present in the cosmetic cleansing compositions according to the invention in specific quantitative ranges:
  • nonionic surfactant c) 0.1 to 5% by weight
  • the proportion by weight of the at least one anionic surfactant of the formula (I) in the total weight of the composition is preferably 1 to 20% by weight, more preferably 2 to 15% by weight and in particular at least 3 to 10% by weight,
  • the proportion by weight of the at least one anionic surfactant of the formula (II) in the total weight of the composition preferably 0.5 to 15 wt .-%, more preferably 1 to 10 wt .-% and in particular at least 2 to 7.5 wt .-%, and the proportion by weight of the at least one C2-C4 mono- and / or dialkanolamide of at least one Cs-C24 carboxylic acid in the total weight of the composition preferably 0.1 to 5 wt .-%, more preferably 0.5 to 4 wt .-% and in particular 1 to 3 wt .-% is.
  • the handle of the foam produced with the agents according to the invention and the creaminess of the foam can be further increased if the detergents contain the surfactants a), b) and c) in a certain weight ratio.
  • cosmetic cleansing compositions according to the invention are accordingly characterized in that they preferably contain the surfactants a), b) and c) in a weight ratio of (1-4) :( 1-3) :( 0.5-2), particularly preferably from (2-4): (1, 5-2.5): (0.75-1, 5).
  • An object of the invention was to provide particularly mild, foamy cosmetic compositions, which could be achieved by the combination of the surfactants a), b) and c).
  • the amount of foam produced by the agents according to the invention corresponds approximately to the amount of foam that can be achieved with alkyl ether sulfate-based cleaning agents, wherein the compositions according to the invention have a higher mildness.
  • the additional use of anionic alkyl ether sulfates in the cleaning agents according to the invention is therefore not necessary.
  • cosmetic cleansing compositions according to the invention are therefore characterized in that the proportion by weight of sulfate-containing surfactants in the total weight of the compositions is preferably less than 0.5% by weight, more preferably less than 0.3% by weight and in particular less than 0.2 wt .-% is.
  • the amount of foam, the foaming properties (in particular the high foam density) and / or the mildness of the compositions according to the invention could be further increased if special amphoteric surfactants were added to them.
  • Suitable amphoteric and / or zwitterionic surfactants preferably correspond to at least one compound of the following formulas (i) to (vii), in which the radical R is a straight-chain or branched, saturated or mono- or polyunsaturated alkyl or alkenyl radical having 7 to 23 carbon atoms (Formulas (i) and (ii)) or represents a straight-chain or branched, saturated or mono- or polyunsaturated alkyl or alkenyl radical having 8 to 24 carbon atoms (formulas (iii) to (vii)),
  • Preferred amphoteric and / or zwitterionic surfactants of the abovementioned formulas (i) to (vii) contain as radical R predominantly a straight-chain or branched, saturated, mono- or polyunsaturated alkyl radical having 8 to 20, more preferably 8 to 16 and in particular with 8 to 12 carbon atoms.
  • amphoteric and / or zwitterionic surfactants in which the radical R is derived from coconut oil.
  • amphoteric and / or zwitterionic surfactants of the formulas (iii), (v), (vi) and (vii).
  • amphoteric surfactants known under the INCI names cocamidopropyl betaine and / or cocoampho (di) acetate and commercially available from several suppliers.
  • the proportion by weight of the amphoteric / zwitterionic surfactant (s) of one of the abovementioned formulas (i) to (vii) in the total weight of the cosmetic compositions of the use according to the invention is preferably from 0.1 to 15% by weight, preferably from 0.5 to 12.5 wt .-% and in particular from 1 to 10 wt .-%.
  • cosmetic cleansing compositions according to the invention are therefore characterized in that they additionally contain at least one amphoteric surfactant, preferably an amphoteric surfactant according to one of the formulas (i) to (vii), where the weight fraction of the amphoteric surfactant is based on the total weight of the composition preferably 0, 1 to 15 wt .-%, more preferably 0.5 to 12.5 wt .-% and in particular 1 to 10 wt .-% is.
  • the surfactant mixture a), b) and c) in addition to the surfactant mixture a), b) and c), they additionally contain a conditioning agent complex d). It has been found that specific active substance complexes in combination with the surfactant combination a), b) and c) are particularly suitable for imparting a high care effect to the cleansing compositions according to the invention. In particular, the wet and dry combability of the hair could be further increased by adding the active ingredient complex.
  • cosmetic cleansing compositions according to the invention are accordingly characterized in that they additionally comprise at least one conditioning active complex d) containing at least one silicone compound and at least one cationic polymer.
  • Silicones have excellent conditioning properties on the hair. In particular, in many cases have a positive effect on the hair and the softness of the hair.
  • Suitable silicone compounds in the context of the present invention may be selected from:
  • polyalkyl siloxanes polyaryl siloxanes, polyalkylaryl siloxanes which are volatile or nonvolatile, straight chain, branched or cyclic, crosslinked or uncrosslinked;
  • grafted silicone polymers having a non-silicone organic backbone consisting of an organic backbone formed from organic monomers containing no silicone grafted with at least one polysiloxane macromer in the chain and optionally at least one chain end;
  • silicone compounds which are particularly suitable according to the invention are:
  • R 5 to R 5 independently of one another represent a radical from the group consisting of alkyl, aryl or alkylaryl having 1 to 30 C atoms,
  • R 6 is a radical which carries at least one quaternary ammonium group
  • x is a number in the range of 2 to 200, and / or
  • the radical R is a hydrogen atom, an alkyl group having 1 to 12 C atoms, an alkoxy group having 1 to 12 C atoms or a hydroxyl group,
  • x is a number from 1 to 100, preferably from 20 to 30,
  • y is a number from 1 to 20, preferably from 2 to 10, and
  • a and b are numbers from 0 to 50, preferably from 10 to 30.
  • preferred silicones according to formula (III) stands
  • the radical R is an aryl radical, preferably a phenyl radical
  • radicals R 2 to R 5 are identical C 1 -C 4 -alkyl radicals, preferably methyl radicals,
  • the radical R 6 is a radical of the structure -R 7 -R 8 , where
  • the group -R 7 - represents at least one grouping of the following formulas (V) to (VIII)
  • y is a number from 2 to 18,
  • z is a number from 0 to 3 and
  • R 9 is hydrogen, a C 1 -C 4 -alkyl group, a C 2 -C 4 -hydroxyalkyl group or an OH group, and
  • the group -R 8 corresponds to at least one of the following formulas (IX) or (X),
  • R 0 and R 2 are each independently of one another hydrogen or an alkyl radical having 1 to 30 C atoms,
  • R is an alkyl radical having 1 to 30 C atoms or a grouping - (CH 2 ) b-NR 0 R 12 , in which b is a number from 2 to 18,
  • R 3 represents a grouping -O- or -N (H) -
  • R 4 is an alkyl radical having 1 to 30 C atoms
  • a stands for a number from 2 to 18 and
  • Suitable C 1 -C 4 -alkyl groups include methyl, ethyl, n-propyl, isopropyl and n-butyl groups. Preference is given to methyl and ethyl groups. Especially preferred are methyl groups.
  • suitable C 2 -C 4 hydroxyalkyl groups are hydroxyethyl, 1-hydroxypropyl, 2
  • Halide ions preferably chloride or bromide ions understood.
  • x is a number from 3 to 120
  • the radical R represents a phenyl radical
  • radicals R 2 to R 5 are methyl radicals
  • the radical R 6 is a radical having the structure -R 7 -R 8 , where
  • x is a number from 8 to 80
  • the radical R represents a phenyl radical
  • radicals R 2 to R 5 are methyl radicals
  • the radical R 6 is a radical having the structure -R 7 -R 8 , where
  • the grouping -R 7 - corresponds to a grouping of the formula (V), in which y is the number 3, z is the number 1 and R 9 is an -OH group, and
  • the group -R 8 corresponds to the formula (X), in which R 0 and R 2 are methyl groups, a is the number 3, R 3 is the grouping -N (H) - and R 4 is a Cs-ds-alkyl group.
  • a silicone compound of the formula (III) which is particularly suitable for the cosmetic cleansing compositions according to the invention is known, for example, under the INCI name Silicone Quaternium-22 and is commercially available.
  • An example of a measure based on a silicone compound having the INCI designation Silicone Quaternium-22 commercial product that can be used in the inventive cleaning compositions is Abil Quat ® T 60 from Evonik.
  • Abil ® T Quat 60 contains a mixture of the ingredients known under the INCI names Silicone Quaternium-22 (65%) and PPG-3 Myristyl Ether (35%).
  • Preferred silicones according to formula (IV) are water-soluble.
  • water-soluble is to be understood as meaning those silicones which have a solubility of at least 2 g / 100 g of water under standard conditions (25 ° C., 1013 mbar.)
  • Particularly preferred silicones b) have at least one water solubility, each under standard conditions , of at least 5 g / 100 g of water, more preferably of at least 10 g / 100 g of water, and in particular preferred silicones according to formula (IV) are completely water-soluble, which is to be understood as forming a solution in any proportion with water.
  • silicones according to formula (IV) are non-volatile. It has been found that it is advantageous for a simpler preparation of the cosmetic cleansing compositions according to the invention if the silicones b) are liquid under standard conditions (25 ° C., 1013 mbar).
  • Particularly preferred silicones of formula (IV) are, for example, under the CTFA designation dimethicone copolyol known and commercially available for example under the names Silsoft ® (Momentive), Silwet ® (General Electric), Dow Corning ® (Dow), Belsil ® (Wacker) and Abil ® (Goldschmidt) available.
  • the silicones of formula (IV) with the CTFA designation dimethicone copolyol contain, and which can be used in the inventive cleaning compositions, Silwet ® L 722 (General Electric), Silwet ®, for example, Silsoft ® 895 (Momentive), 7001 (General Electric), Silwet ® 7605 (General Electric), Silwet ® 7500 (General Electric), Dow Corning ® 190 (Dow), Dow Corning ® 193 (Dow), Dow Corning ® 3225 (Dow), Belsil ® DMC 6031 ( Wacker) and / or Abil ® 8842 (Goldschmidt).
  • Silwet ® L 722 General Electric
  • Silwet ® for example, Silsoft ® 895 (Momentive), 7001 (General Electric), Silwet ® 7605 (General Electric), Silwet ® 7500 (General Electric), Dow Corning ® 190 (Dow), Dow Corning ® 193 (Dow), Dow Corning ® 3225
  • the proportion by weight of the at least one silicone compound in the total weight of the cosmetic cleaning agents is preferably 0.01 to 10 wt .-%, more preferably 0.05 to 7.5 wt .-%, particularly preferably 0.075 to 6 wt .-% and in particular 0, 1 to 4 wt .-%.
  • Suitable cationic polymers are, for example:
  • quaternized cellulose derivatives such as are available under the names of Celquat ® and Polymer JR ® commercially
  • quaternized cellulose derivatives which may be hydrophobically modified, for example
  • honey for example the commercial product Honeyquat ® 50,
  • cationic guar derivatives such as those under the trade names Cosmedia ® guar
  • Such compounds are sold under the names Gafquat ® 734 and Gafquat ® 755 commercially,
  • Vinylpyrrolidone vinylimidazoliummethochloride copolymers such as those offered under the names Luviquat.RTM ® FC 370, FC 550, FC 905 and HM 552,
  • Polyquaternium 2 Polyquaternium 17, Polyquaternium 18, Polyquaternium-24, Polyquaternium 27, Polyquaternium-32, Polyquaternium-37, Polyquaternium 74 and Polyquaternium 89 known polymers.
  • Preferred cationic polymers are preferably selected from the polymers known by the INCI names Guar Hydroxypropyltrimonium Chloride, Polyquaternium-67, Polyquaternium-10, Polyquaterniu-6, Polyquaternium-7 and / or Polyquaternium-37. Particularly preferred are the polymers known under the INCI names guar hydroxypropyltrimonium chlorides, polyquaternium-6, polyquaternium-7 and polyquaternium-10 known polymers.
  • the proportion by weight of the cationic polymer (s) in the total weight of the cosmetic cleaners is preferably from 0.01 to 10% by weight, more preferably from 0.025 to 7.5% by weight, particularly preferably from 0.05 to 6% by weight and in particular 0 , 1 to 5 wt .-%.
  • cosmetic cleansing compositions according to the invention are particularly preferred which comprise at least one conditioning active complex d) which
  • R 5 to R 5 independently of one another represent a radical from the group consisting of alkyl, aryl or alkylaryl having 1 to 30 C atoms,
  • R 6 is a radical which carries at least one quaternary ammonium group
  • x is a number in the range of 2 to 200, and / or
  • the radical R is a hydrogen atom, an alkyl group having 1 to 12 C atoms, an alkoxy group having 1 to 12 C atoms or a hydroxyl group, x is a number from 1 to 100, preferably from 20 to 30,
  • y is a number from 1 to 20, preferably from 2 to 10, and
  • a and b are numbers from 0 to 50, preferably from 10 to 30, and
  • Particularly preferred cosmetic cleaners within this fourth preferred embodiment contain as active ingredient complex d) preferably at least one under the INCI name Silicone Quaternium-22 and / or at least one known under the INCI name PEG-12 Dimethicone silicone compound and at least one of the INCI Designations Polyquaternium-6, Polyquaternium-7, Polyquaternium-10 and / or Guar Hydroxypropyltrimonium Chloride known cationic polymers.
  • the proportion by weight of the conditioning active complex d) in the total weight of the composition is preferably 0, 1 to 10 wt .-%, more preferably 0.25 to 7.5 wt .-% and in particular 0.5 to 5 wt .-%.
  • cosmetic cleansing compositions according to the invention are characterized in that they
  • R 2 to R 5 is a methyl radical and the other radicals are a hydrogen atom
  • R is a linear or branched, saturated or unsaturated alkyl radical having 8 to 18 carbon atoms
  • M + is a sodium, potassium or ammonium ion.
  • R ' is a linear, saturated alkyl radical having 8 to 18 carbon atoms, n is a number from 1 to 8, and
  • X is a sodium, potassium or ammonium ion
  • c) contain at least one monoethanolamide of a Cs-Os carboxylic acid
  • Cleaning agent preferably 1 to 20 wt .-%
  • Cleaning agent preferably 0.5 to 15 wt .-%
  • Cleaning agent preferably 0, 1 to 5, and
  • Detergent is preferably 0, 1 to 10 wt .-%. Within this embodiment, cleaning agents according to the invention are particularly preferred which
  • At least one active substance complex d) which contains at least one silicone compound known under the INCI name Silicone Quaternium-22 and / or at least one silicone compound known under the INCI name PEG-12 Dimethicone and at least one of the INCI names Polyquaternium-6, Polyquaternium-7, polyquaternium-10 and / or guar hydroxypropyltrimonium chloride known cationic polymers, wherein
  • Cleaning agent preferably 3 to 10 wt .-%
  • Cleaning agent preferably 2 to 7.5 wt .-%
  • Cleaning agent preferably 1 to 3 wt .-%
  • Detergent preferably 0.5 to 5 wt .-% is.
  • the care properties of the cosmetic compositions can be further increased if they additionally contain at least one further conditioning agent, which may be selected from the group of
  • Suitable protein hydrolysates are product mixtures which can be obtained by acid, alkaline or enzymatically catalyzed degradation of proteins (proteins).
  • Animal protein hydrolysates are, for example, elastin, collagen, keratin, silk and milk protein hydrolysates, which may also be present in the form of salts.
  • Such products are, for example, under the trademarks Dehylan ® (Cognis), Promois ® (Interorgana) Collapuron ® (Cognis), Nutrilan® ® (Cognis), Gelita-Sol ® (German Gelatinefabriken Stoess & Co), Lexein ® (Inolex) and kerasol tm ® (Croda) sold.
  • Protein hydrolysates of plant origin eg. Soybean, almond, rice, pea, potato and wheat protein hydrolysates.
  • Such products are, for example, under the trademarks Gluadin ® (Cognis), diamine ® (Diamalt) ® (Inolex) and Crotein ® (Croda) available.
  • cationized protein hydrolysates the protein hydrolyzate on which the animal is based, for example from collagen, milk or keratin, from the plant, for example from wheat, maize, rice, potatoes, soy or almonds, from marine life forms, for example from fish collages or algae, or from biotechnologically derived protein hydrolysates.
  • the protein hydrolyzates on which the cationic derivatives are based can be obtained from the corresponding proteins by chemical, in particular alkaline or acid hydrolysis, by enzymatic hydrolysis and / or a combination of both types of hydrolysis.
  • the hydrolysis of proteins usually results in a protein hydrolyzate having a molecular weight distribution of about 100 daltons up to several thousand daltons.
  • cationic protein hydrolyzates whose underlying protein content has a molecular weight of 100 to 25,000 daltons, preferably 250 to 5000 daltons.
  • cationic protein hydrolyzates are to be understood as meaning quaternized amino acids and mixtures thereof.
  • the quaternization of the protein hydrolyzates or amino acids is often carried out using quaternary ammonium salts such as N, N-dimethyl-N- (n-alkyl) -N- (2-hydroxy-3-chloro-n-propyl) ammonium halides.
  • the cationic protein hydrolysates may also be further derivatized.
  • Typical examples of the cationic protein hydrolysates and derivatives include the products known and commercially available under the INCI names: Cocodimonium Hydroxypropyl Hydrolyzed Collagen, Cocodimopnium Hydroxypropyl Hydrolyzed Casein, Cocodimonium Hydroxypropyl Hydrolyzed Collagen, Cocodimonium Hydroxypropyl Hydrolyzed Hair Keratin, Cocodimonium Hydroxypropyl Hydrolyzed Keratin , Cocodimonium Hydroxypropyl Hydrolyzed Rice Protein, Cocodimonium Hydroxypropyl Hydrolyzed Silk, Cocodimonium Hydroxypropyl Hydrolyzed Soy Protein, Cocodimonium Hydroxypropyl Hydrolyzed Wheat Protein, Cocodimonium Hydroxypropyl Silk Amino Acids, Hydroxypropyl Arginine Lauryl / Myristyl Ether HCl, Hydroxypropyltrimonium Gelatin, Hydroxypropyltrimonium Hydrolyzed Case
  • the proportion by weight of the protein hydrolyzate (s) in the total weight of the cosmetic compositions is preferably from 0.01 to 5% by weight, more preferably from 0.025 to 3% by weight and in particular from 0.05 to 2% by weight.
  • Suitable vitamins are preferably the following vitamins, provitamins and vitamin precursors and their derivatives:
  • Vitamin A the group of substances called vitamin A includes retinol (vitamin Ai) and 3,4-didehydroretinol (vitamin A2).
  • the ß-carotene is the provitamin of retinol.
  • vitamin A component for example, vitamin A acid and its esters, vitamin A aldehyde and vitamin A alcohol and its esters such as palmitate and acetate into consideration.
  • Vitamin B may belong to the vitamin B group or to the vitamin B complex. a.
  • Vitamin B3 > Vitamin B3.
  • the compounds nicotinic acid and nicotinamide (niacinamide) are often performed.
  • panthenol is preferred.
  • Useful derivatives of panthenol are in particular the esters and ethers of panthenol, pantolactone and cationically derivatized panthenols. Individual representatives are, for example, panthenol triacetate, panthenol monoethyl ether and its monoacetate, as well as cationic panthenol derivatives.
  • Vitamin ⁇ (pyridoxine and pyridoxamine and pyridoxal).
  • Vitamin C ascorbic acid: use in the form of palmitic acid ester, glucosides or phosphates may be preferred. The use in combination with tocopherols may also be preferred.
  • Vitamin E tocopherols, especially a-tocopherol
  • Vitamin F the term "vitamin F” is usually understood as meaning essential fatty acids, in particular linoleic acid, linolenic acid and arachidonic acid.
  • Vitamin H Vitamin H is the compound (3aS, 4S, 6aR) -2-oxohexahydrothienol [3,4-d] - imidazole-4-valeric acid, for which, in the meantime, the trivial name biotin has prevailed.
  • vitamins, provitamins and vitamin precursors from groups A, B, E and H Particular preference is given to nicotinamide, biotin, pantolactone and / or panthenol.
  • the proportion by weight of the vitamin (s), vitamin derivative (s), and / or the vitamin precursor (s) in the total weight of the cosmetic compositions is preferably from 0.001 to 2% by weight, particularly preferably from 0.005 to 1% by weight and in particular 0 , 01 to 0.5 wt .-%.
  • Suitable oil, wax and / or fat components may preferably be selected from mineral or natural oil components and / or fatty substances.
  • natural (vegetable) oils usually triglycerides and mixtures of triglycerides are used.
  • Preferred natural oils are coconut oil, (sweet) almond oil, walnut oil, peach kernel oil, apricot kernel oil, avocado oil, tea tree oil, soybean oil, sesame oil, sunflower oil, tsubaki oil, evening primrose oil, rice bran oil, palm kernel oil, mango seed oil, meadowfoam seed oil, thistle oil, macadamia nut oil, grapeseed oil, Amaranth seed oil, argan oil, bamboo oil, olive oil, wheat germ oil, pumpkin seed oil, mallow oil, hazelnut oil, safflower oil, canola oil, sasanqua oil, jojoba oil, rambutan oil, cocoa butter and shea butter.
  • mineral oils are used in particular mineral oils, paraffin and Isoparaffinöle and synthetic hydrocarbons.
  • An example of a usable hydrocarbon is for example that available as a commercial product 1, 3-di- (2-ethylhexyl) - cyclohexane (Cetiol ® S).
  • oil component may further serve a dialkyl ether.
  • dialkyl ethers are, in particular, di-n-alkyl ethers having a total of from 12 to 36 carbon atoms, in particular from 12 to 24 carbon atoms, such as, for example, di-n-octyl ether, di-n-decyl ether, di-n-nonyl ether, di-n -undecyl ether, di-n-dodecyl ether, n-hexyl n-octyl ether, n-octyl n-decyl ether, n-decyl n-undecyl ether, n-undecyl n-dodecyl ether and n-hexyl n-undecyl ether and di tert-butyl ether, di-iso-pentyl ether, di-3-ethyl decyl ether, tert-butyl n-oct
  • Fatty substances are to be understood fatty acids, fatty alcohols and natural and synthetic waxes, which may be present both in solid form and liquid in aqueous dispersion.
  • the fatty acids used can be linear and / or branched, saturated and / or unsaturated fatty acids having 6 to 30 carbon atoms. Preference is given to fatty acids having 10 to 22 carbon atoms. Among these could be mentioned, for example, isostearic as the commercial products Emersol ® 871 and Emersol ® 875, and isopalmitic acids such as the commercial product Edenor ® IP 95, and all other products sold under the trade names Edenor ® (Cognis) fatty acids.
  • fatty acids are caproic, caprylic, 2-ethylhexanoic, capric, lauric, isotridecanoic, myristic, palmitic, palmitoleic, stearic, isostearic, oleic, elaidic, petroselic, linoleic, Linolenic acid, elaeostearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures.
  • fatty acid cuttings obtainable from coconut oil or palm oil;
  • stearic acid is usually preferred.
  • fatty alcohols it is possible to use saturated, mono- or polyunsaturated, branched or unbranched fatty alcohols with C6-C30, preferably C10-C22 and very particularly preferably C12-C22, carbon atoms.
  • the fatty alcohols are derived from preferably natural fatty acids, which can usually be based on recovery from the esters of fatty acids by reduction.
  • those fatty alcohol cuts which are produced by reduction of naturally occurring triglycerides such as beef tallow, palm oil, peanut oil, rapeseed oil, cottonseed oil, soybean oil, sunflower oil and linseed oil or fatty acid esters formed from their transesterification products with corresponding alcohols, and thus represent a mixture of different fatty alcohols.
  • Such substances are, for example, under the names Stenol ® such as Stenol ® 1618 or Lanette ® such as Lanette ® O or Lorol ®, for example, Lorol ® C8, Lorol C14 ®, Lorol C18 ®, ® Lorol C8-18, HD-Ocenol ®, Crodacol ® such as Crodacol ® CS, Novol ®, Eutanol ® G, Guerbitol ® 16, Guerbitol ® 18, Guerbitol ® 20, Isofol ® 12, Isofol ® 16, lsofol ® 24, Isofol ® 36, Isocarb ® 12, Isocarb ® 16 or acquire Isocarb® ® 24 for sale.
  • Stenol ® such as Stenol ® 1618 or Lanette ® such as Lanette ® O or Lorol ®
  • Lorol ® C8 Lorol C8-18
  • wool wax alcohols as are commercially available, for example under the names of Corona ®, White Swan ®, Coronet ® or Fluilan ® can be used according to the invention.
  • natural or synthetic waxes there may be used solid paraffins or isoparaffins, carnauba waxes, beeswaxes, candelilla waxes, ozokerites, ceresin, spermaceti, sunflower wax, fruit waxes such as apple wax or citrus wax, microwaxes of PE or PP.
  • Such waxes are available, for example, from Kahl & Co., Trittau.
  • fatty substances are, for example
  • Ester oils are the esters of C6-C30 fatty acids with C2-C30 fatty alcohols.
  • the monoesters of the fatty acids with alcohols having 2 to 24 carbon atoms are preferred.
  • Examples of fatty acid components used in the esters are caproic, caprylic, 2-ethylhexanoic, capric, lauric, isotridecanoic, myristic, palmitic, palmitoleic, stearic, isostearic, oleic, elaidic, petroselic, linoleic, linolenic Behenic acid and erucic acid and their technical mixtures.
  • fatty alcohol components in the ester oils are isopropyl alcohol, caproic alcohol, capryl alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, elaeostearyl alcohol, arachyl alcohol, Gadoleyl alcohol, behenyl alcohol, erucyl alcohol and brassidyl alcohol and their technical mixtures.
  • isopropyl myristate IPM Rilanit ®
  • isononanoic acid C16-18 alkyl ester Cetiol ® SN
  • 2-ethylhexyl palmitate Cegesoft ® 24
  • stearic acid-2-ethylhexyl ester Cetiol ® 868
  • cetyl oleate glycerol tricaprylate, caprate Kokosfettalkohol- / caprylate (Cetiol ® LC)
  • n-butyl stearate oleyl erucate
  • isopropyl palmitate IPP Rilanit ®
  • oleyl Oleate Cetiol ®
  • hexyl laurate Cetiol ® A
  • di-n-butyl adipate Cetiol ® B
  • Dicarboxylic acid esters such as di-n-butyl adipate, di (2-ethylhexyl) adipate, di- (2-ethylhexyl) succinate and di-isotridecyl acelate
  • diol esters such as ethylene glycol dioleate, ethylene glycol diisotridecanoate, propylene glycol di (2 ethylhexanoate), propylene glycol diisostearate, propylene glycol di-pelargonate, butanediol diisostearate, neopentyl glycol dicaprylate,
  • ethoxylated or non ethoxylated mono, - di- and trifatty acid esters of saturated and / or unsaturated linear and / or branched fatty acids with glycerol such as Monomuls 90-018 ®, ® Monomuls 90-L12, Cetiol ® HE or Cutina ® MD.
  • the proportion by weight of the oil, wax and / or fat components in the total weight of the cosmetic compositions is preferably 0.01 to 5 wt .-%, particularly preferably 0.025 to 4 wt .-% and in particular 0.05 to 3 wt .-%.
  • Glycerol may be added to the cosmetics separately in an amount of up to 10% by weight (based on the total weight of the detergent). It may also be part of the aqueous-alcoholic carrier.
  • cosmetic compositions according to the invention are also suitable for use as antidandruff preparations.
  • the total weight of anti-dandruff agents in the total weight of the cosmetic compositions may preferably 0.01 to 10 wt .-%, more preferably 0.025 to 7.5 wt .-%, particularly preferably 0.05 to 5 wt .-% and in particular 0.075 to 3 wt .-% amount.
  • Suitable antidandruff active ingredients may be selected from Piroctone olamine, climbazole, zinc pyrithione, ketoconazole, salicylic acid, sulfur, selenium sulfide, tar preparations, undecenoic acid derivatives, burdock root extracts, poplar extracts, nettle extracts, walnut shell extracts, birch extracts, willow bark extracts, rosemary extracts and / or arnica extracts.
  • Further active ingredients, auxiliaries and additives which may preferably be present in the cosmetic compositions according to the invention are, for example:
  • Thickening agents such as gelatin or vegetable gums, for example agar-agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans, cellulose derivatives, e.g. As methylcellulose, hydroxyalkylcellulose and carboxymethylcellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays and phyllosilicates such. As bentonite or fully synthetic hydrocolloids such.
  • polyvinyl alcohol the Ca, Mg or Zn - soaps,
  • Thickeners such as acrylic and methacrylic (co) polymers, for example, the crosslinked homopolymers of acrylic acid (INCI name: Carbomer), which are also referred to as carboxyvinyl polymers.
  • Such polyacrylic acids are inter alia from the company. 3V Sigma under the trade name Polygel®, z. B. Polygel DA and from B.F. Goodrich under the trade name Carbopol® available, z. Carbopol 940 (molecular weight about 4,000,000), Carbopol 941 (molecular weight about 1 250,000) or Carbopol 934 (molecular weight about 3,000,000).
  • the following acrylic acid copolymers are suitable:
  • Copolymers of two or more monomers from the group of acrylic acid, methacrylic acid and their simple, preferably with C1-C4-alkanols formed ester (INCI name: Acrylates Copolymer), such as the copolymers of methacrylic acid, butyl acrylate and methyl methacrylate or butyl acrylate and methyl methacrylate, and which are available, for example, from Rohm & Haas under the trade names Aculyn® and Acusol® and from Degussa (Goldschmidt) under the trade name Tego® Polymer, eg Aculyn 22, Aculyn 28, Aculyn 33 (cross-linked), Acusol 810, Acusol 820, Acusol 823 and Acusol 830;
  • crosslinked high molecular weight acrylic acid copolymers such as those crosslinked with an allyl ether of sucrose or pentaerythritol copolymers of C10-C30 alkyl acrylates with one or more monomers selected from the group consisting of acrylic acid, methacrylic acid and their simple, preferably with C1-C4 alkanols , Esters (INCI name: acrylates (C10-C30) -alkyl acrylate crosspolymer), and which are available, for example, from the company BF Goodrich under the trade name Carbopol®, z. Carbopol ETD 2020 and Carbopol 1382 (INCI Acrylates (C10-C30) alkyl acrylate crosspolymer) and Carbopol Aqua 30,
  • Structurants such as maleic acid and lactic acid
  • Dyes for staining the agent for example ⁇ - and ⁇ -hydroxycarboxylic acids such as citric acid, lactic acid, malic acid, glycolic acid,
  • Active ingredients such as bisabolol,
  • Ceramides are understood as meaning N-acylsphingosine (fatty acid amides of sphingosine) or synthetic analogs of such lipids (so-called pseudo-ceramides),
  • Propellants such as propane-butane mixtures, N 2 O, dimethyl ether, CO 2 and air,
  • Preservatives such as sodium benzoate or salicylic acid
  • Additional viscosity regulators such as salts (NaCl).
  • the cosmetic compositions according to the invention may preferably have a pH in the range from 3 to 7, more preferably from 4 to 6.5, particularly preferably from 4.5 to 6.6 and in particular from 5 to 6.
  • the cosmetic compositions according to the invention preferably have a viscosity in the range from 1, 000 to 15,000 mPas, preferably from 1, 500 to 12,500 mPas and in particular from 3,000 to 10,000 mPas (measured in each case with a Haake VT550 20 ° C rotary viscometer, measuring device MV Spindle MV II; 8 rpm).
  • Compositions of such a viscosity can be well distributed on the respective application surface - particularly preferably on the hair - and, if appropriate, rinse off again with water after use.
  • compositions A and B were prepared (compositions A and B in the table below; amounts in [% by weight]):
  • compositions A and B the following commercial products were used:
  • the care of the hair during cleaning could be improved with the compositions according to the invention, which is particularly noticeable in the improved combability of the hair (wet and dry combability).

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Abstract

L'invention concerne un produit cosmétique nettoyant particulièrement doux, moussant et traitant, qui contient, dans un support approprié, a) au moins un premier tensioactif anionique de la formule (I), dans laquelle au moins un des restes R2 à R5 représente un reste alkyle C1-C4 et les autres restes représentent indépendamment les uns des autres un atome d'hydrogène ou un reste alkyle C1-C4, R1 représente respectivement un reste alkyle linéaire ou ramifié, saturé ou insaturé, comprenant 6 à 30 atomes de carbone, et M+ représente un ammonium, un alcanolammonium ou un cation métallique, b) au moins un deuxième tensioactif anionique de la formule (II), dans laquelle R1 représente un reste alkyle linéaire ou ramifié, saturé ou insaturé, comprenant 6 à 30 atomes de carbone, n représente un chiffre de 0 à 20, de préférence de 1 à 10, X représente un ammonium, un alcanolammonium ou un cation métallique et c) au moins un mono- et/ou di-alcanolamide C2-C4 au moins d'un acide carboxylique C8-C24.
EP14806666.5A 2013-12-17 2014-12-05 Produit cosmétique nettoyant doux Withdrawn EP3082749A1 (fr)

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JP7481470B2 (ja) 2020-02-27 2024-05-10 ザ プロクター アンド ギャンブル カンパニー 有効性及び美観が強化された硫黄含有フケ防止組成物
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