WO2012076345A1 - Composition cosmétique comprenant un acide imidoperoxycarboxylique, un acide imidocarboxylique et un copolymère d'acide 2-acrylamido-2-méthyl- propanesulfonique - Google Patents

Composition cosmétique comprenant un acide imidoperoxycarboxylique, un acide imidocarboxylique et un copolymère d'acide 2-acrylamido-2-méthyl- propanesulfonique Download PDF

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Publication number
WO2012076345A1
WO2012076345A1 PCT/EP2011/071050 EP2011071050W WO2012076345A1 WO 2012076345 A1 WO2012076345 A1 WO 2012076345A1 EP 2011071050 W EP2011071050 W EP 2011071050W WO 2012076345 A1 WO2012076345 A1 WO 2012076345A1
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Prior art keywords
acid
weight
composition
compound
formula
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PCT/EP2011/071050
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English (en)
Inventor
Véronique Chevalier
Benoit Muller
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L'oreal
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Publication of WO2012076345A1 publication Critical patent/WO2012076345A1/fr

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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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/38—Percompounds, e.g. peracids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/042—Gels
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
    • 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
    • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • 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
    • A61Q19/008—Preparations for oily skin
    • 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
    • A61K2800/52—Stabilizers

Definitions

  • Cosmetic composition comprising an imidoperoxycarboxylic acid, an imidocarboxylic acid and copolymer of 2-acrylamido-2- methylpropanesulphonic acid
  • the invention relates to a composition, in particular a cosmetic composition, comprising an imidoperoxycarboxylic acid derivative, an imidocarboxylic acid derivative and a copolymer of 2-acrylamido-2-methylpropanesulphonic acid. It also relates to a method for cosmetic treatment of the skin that uses the said composition.
  • 6-Phthalimidoperoxyhexanoic acid is a compound sold by Solvay as an active deodorant, bacteriostatic and decolourizing agent.
  • Patent US 6,471 ,947 describes an aqueous cosmetic composition for oral use for the whitening of the teeth, which contains 6-phthalimidoperoxyhexanoic acid.
  • Patent application WO 2005/068470 describes aqueous compositions comprising 6- phthalimidoperoxyhexanoic acid and a nonionic surfactant.
  • compositions comprising 6-phthalimidoperoxyhexanoic acid are also described in documents EP-A-2105165 and WO 2009/001296.
  • 6-Phthalimidoperoxyhexanoic acid is an active ingredient which is difficult to formulate, in particular in aqueous media, more particularly in conventional vectors of cosmetic compositions or detergents (laundering compositions, surface cleaners), because of its chemical instability: the compound degrades. This degradation gives rise to a substantial loss of activity on the part of the compound.
  • imidoperoxycarboxylic acid derivatives can be stabilized when they are combined with imidocarboxylic acid or derivatives thereof in a particular weight ratio. This combination, indeed, is stable for 2 months at 45°C.
  • the invention accordingly relates to a composition
  • a composition comprising, in an aqueous vehicle medium, a) an imidoperoxycarboxylic acid of formula (I) as defined below, b) an imidocarboxylic acid of formula (II) as defined below, and c) a copolymer of 2-acrylamido- 2-methylpropanesulphonic acid and C2-C4 hydroxyalkyi (meth)acrylate, the compounds (I) and (II) being present in a compound (l)/compound (II) weight ratio of from 4 to 20.
  • the vehicle medium of the composition is advantageously an aqueous medium.
  • the vehicle medium of the composition is a physiologically acceptable medium, and more particularly a physiologically acceptable aqueous medium.
  • the invention likewise provides a method for cosmetic, non-therapeutic, treatment of the skin that comprises applying to the skin a composition comprising, in a vehicle medium, an imidoperoxycarboxylic acid of formula (I) as defined below and an imidocarboxylic acid of formula (II) as defined below, the compounds (I) and (II) being present in a compound (l)/compound (II) weight ratio of from 4 to 20.
  • the imidoperoxycarboxylic acid used in the composition according to the invention is selected from the compounds of formula (I) below:
  • - A represents a benzene ring which is optionally substituted by one or more, preferably up to 4, more preferably by 1 or 2 groups selected from a (d-C 5 )alkyl group,
  • - R represents a hydrogen atom, an -OH group, a (CrC 5 )alkyl group, a -COOH group, or a group -COOR 1 , where represents a (C C 5 )alkyl group, and
  • - n is an integer from 1 to 12, for example from 1 to 8, for example from 1 to 5, or for example from 3 to 5,
  • the imidoperoxycarboxylic acid derivative used in the composition according to the invention is selected from the compounds of formula (II) below:
  • - A' represents a benzene ring which is optionally substituted by one or more, preferably up to 4, more preferably by 1 or 2 groups selected from a (d-C 5 )alkyl group,
  • - m is an integer from 1 to 12, for example from 1 to 10 or for example from 1 to 6, and salts thereof.
  • the salts of the compounds (I) and (II) that can be used according to the invention are particularly selected from alkali metal salts, for example sodium and potassium salts; alkaline earth metal salts, for example calcium, magnesium and strontium salts, metal salts, for example zinc, aluminium, manganese and copper salts; salts of ammonium of formula NH 4 + ; quaternary ammonium salts; salts of organic amines, such as, for example, methylamine, dimethylamine, trimethylamine, triethylamine, ethylamine, 2- hydroxyethylamine, bis(2-hydroxyethyl)amine and tri(2-hydroxyethyl)amine salts; and lysine and arginine salts.
  • Preference is given to using salts selected from sodium, potassium, magnesium, strontium, copper, manganese and zinc salts. More preferably the sodium salt is used.
  • Examples of (CrC 5 )alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and pentyl.
  • a percarboxylic imidoaromatic acid derivative of formula (I) for which A is an unsubstituted benzene ring, R is a hydrogen atom, a -COOH group or a (CrC 3 )alkyl group, and n ranges from 1 to 5. R is preferably a hydrogen atom.
  • A preferably represents an unsubstituted benzene ring
  • n is preferably an integer from 1 to 5.
  • 3-phthalimidoperoxybutanoic acid phthalimidoperoxypentanoic acid, phthalimidoperoxyhexanoic acid, phthalimidoperoxyhexanoic acid, phthalimidoperoxyheptanoic acid, phthalimidoperoxyoctanoic acid, phthalimidoperoxynonanoic acid, phthalimidoperoxydecanoic acid, phthalimidoperoxyundecanoic acid, phthalimidoperoxydodecanoic acid and 2- phthalimidomonoperoxysuccinic acid.
  • the compound of formula (I) is preferably 6-phthalimidoperoxyhexanoic acid, also called phthalimidoperoxycaproic acid or ⁇ -phthalimidoperoxyhexanoic acid. Its chemical structure is as follows:
  • PAP 6-Phthalimidoperoxyhexanoic acid
  • 6-Phthalimidoperoxyhexanoic acid is also available in the form of an aqueous dispersion (containing 17% of active ingredient) under the trade name Eureco ® HC L17 from Solvay. 6-Phthalimidoperoxyhexanoic acid is also provided in the form of a powder under the trade name Eureco ® HC-P11.
  • Aqueous dispersions of 6-phthalimidoperoxyhexanoic acid are described in document EP 1 074 607. These aqueous dispersions are stabilized by copolymers of methyl vinyl ether with maleic acid and/or anhydride, in a 1 : 1 ratio, having an alternating structure.
  • the imidoperoxycarboxylic acid of formula (I) may be present in the composition according to the invention in an amount of from 0.0001 % to 30% by weight, relative to the total weight of the composition.
  • the amount of the said compound of formula (I) may preferably be from 0.001 % to 20% by weight, relative to the total weight of the composition.
  • the amount of the said compound of formula (I) may more particularly be from 0.01 % to 20% by weight, relative to the total weight of the composition.
  • the amount of the said compound of formula (I) may more preferably be from 0.05% to 5% by weight, relative to the total weight of the composition.
  • the invention likewise provides a composition comprising, in a physiological acceptable medium, an acid of formula (II) as described above.
  • the said composition is useful for treating greasy skin. It may therefore be used in a cosmetic method for treating greasy skin that comprises applying the composition to the greasy skin.
  • an imidocarboxylic acid derivative of formula (II) is used for which A' is an unsubstituted benzene ring and m ranges from 1 to 5.
  • A' preferably represents an unsubstituted benzene ring.
  • the compounds of formula (II) include the following:
  • the compound of formula (II) is preferably 6-phthalimidohexanoic acid, also called phthalimidocaproic acid, or ⁇ -phthalimidohexanoic acid (CAS No.: 4443-26-9). Its chemical structure is as follows:
  • the imidocarboxylic acid derivative of formula (II) may be present in the composition according to the invention in an amount of from 0.001 % to 3% by weight, relative to the total weight of the composition.
  • the amount of the said compound of formula (II) may preferably be from 0.005% to 2% by weight, relative to the total weight of the composition.
  • the amount of the said compound of formula (II) may particularly be from 0.01 % to 1 % by weight, relative to the total weight of the composition.
  • the amount of the said compound of formula (II) may more preferably be from 0.05% to 0.5% by weight, relative to the total weight of the composition.
  • This weight ratio is advantageously from 5 to 14.
  • This weight ratio is preferably from 6 to 13.
  • This weight ratio is more preferably from 6.5 to 10.5.
  • This weight ratio is more preferably still from 7.5 to 9.5.
  • composition according to the invention comprises an aqueous medium
  • it may advantageously comprise a copolymer of 2-acrylamido-2-methylpropanesulphonic acid and C2-C4 hydroxyalkyl (meth)acrylate.
  • a copolymer of this kind reinforces the stability of the compounds by maintaining them in suspension in the water and by preventing their chemical degradation over time.
  • the C2-C4 hydroxyalkyl (meth)acrylate monomer may be selected from 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2, 3-d i hydroxy propyl acrylate and 2, 3-d i hydroxy- propyl methacrylate.
  • the composition preferably comprises the 2-acrylamido-2-methylpropanesulphonic acid- 2-hydroxyethyl acrylate copolymer, such as, for example, those sold under the trade names Sepinov ® EMT 10 and Simulgel ® NS by SEPPIC (INCI name: Hydroxyethyl acrylate/sodium acryloyldimethyl taurate copolymer).
  • 2-acrylamido-2-methylpropanesulphonic acid- 2-hydroxyethyl acrylate copolymer such as, for example, those sold under the trade names Sepinov ® EMT 10 and Simulgel ® NS by SEPPIC (INCI name: Hydroxyethyl acrylate/sodium acryloyldimethyl taurate copolymer).
  • the copolymer of 2-acrylamido-2-methylpropanesulphonic acid and C2-C4 hydroxyalkyl (meth)acrylate may be present in the composition according to the invention in an amount of from 0.05% to 20% by weight, relative to the total weight of the composition.
  • the amount of the said copolymer may preferably be from 0.1 % to 10% by weight, relative to the total weight of the composition.
  • the amount of the said copolymer may more preferably be from 0.5% to 5% by weight, relative to the total weight of the composition.
  • the imidoperoxycarboxylic acid derivative of formula (I) (i.e. A) and the copolymer of 2- acrylamido-2-methylpropanesulphonic acid and C2-C4 hydroxyalkyl (meth)acrylate (i.e. B) may advantageously be present in the composition according to the invention in an A/B weight ratio of from 1/5 to 5/1. This A/B weight ratio may preferably be from 1/3 to 3/1. This A/B weight ratio may more preferably be from 0.4 to 1.1. This A/B weight ratio may more preferably still be from 0.5 to 1.
  • the composition according to the invention comprises a physiologically acceptable aqueous medium, in other words an aqueous medium which is non-toxic and can be applied to the keratinous matter of human beings, and which has a pleasant appearance, odour and feel.
  • the composition is in particular a cosmetic composition.
  • the composition according to the invention may comprise water, for example in an amount of from 50% to 99% by weight, relative to the total weight of the composition.
  • the water content of the composition may preferably be from 60% to 97% by weight.
  • composition according to the invention advantageously has a pH of from 3 to 5.
  • the pH of the composition is preferably from 3.5 to 4.2.
  • the pH of the composition may be adjusted for example using aqueous sodium hydroxide solution, citric acid, sodium citrate, potassium citrate, lactic acid, sodium lactate, potassium lactate, glycolic acid, sodium glycolate and/or potassium glycolate.
  • the composition may comprise at least one oil selected from C5-C-15 branched or linear alkanes, silicone oils which are linear or cyclic polydimethylsiloxanes having from 2 to 7 silicon atoms, such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethyl- cyclohexasiloxane, hexamethyldisiloxane, octamethyltnsiloxane, decamethyltetrasiloxane and dodecamethylpentasiloxane, polydimethylsiloxanes (and preferably those with a viscosity of less than 200 est), and capric/caprylic acid trig
  • the oil may be present in the composition according to the invention in an amount of from 0.05% to 50% by weight, relative to the total weight of the composition.
  • the said oil may preferably be present in an amount of from 0.01 % to 30% by weight, relative to the total weight of the composition.
  • the said oil may more preferably be present in an amount of from 1 % to 20% by weight, relative to the total weight of the composition.
  • composition according to the invention may further comprise an active cosmetic ingredient which is stable at acidic pH. It may comprise an active ingredient selected from the following:
  • composition may also comprise other cosmetic additives, with the proviso that the good stability of the compound of formula (I) is maintained.
  • Cosmetic additives include for example xanthan gum, polyvinyl methyl ether/maleic acid copolymer (such as, for example, that sold under the name Gantrez ® S-97 BF by ISP).
  • composition according to the invention may take the form of an aqueous gel or an oil-in-water (O/W) emulsion. It is intended in particular for topical application to the skin.
  • O/W oil-in-water
  • the invention further relates to a cosmetic, non-therapeutic, method for treating the skin, comprising applying to the skin a composition as described above. More particularly the cosmetic treatment method relates to the treatment of greasy skins, and the composition is applied to greasy skins.
  • the composition is applied to the facial zone, more particularly the T zone (forehead, nose, cheeks, chin), more particularly the cheeks and the nose.
  • T zone forehead, nose, cheeks, chin
  • the stability of each gel is evaluated after different storage times and at different temperatures by measuring the amount of 6-phthalimidoperoxyhexanoic acid (acid A).
  • the assay is carried out by measuring the peroxide index in accordance with the standard NFT 60-220; a test sample dissolved in acetic acid and chloroform is treated with a solution of potassium iodide, and the iodine liberated is titrated with a titred solution of sodium thiosulphate.
  • the peroxide index is the amount of product (acid A) present in the sample, expressed in milliequivalents of active oxygen per kilogram, which oxidizes the potassium iodide.
  • composition of gels 2 to 4 may be applied for facial skincare, and more particularly for treating greasy skin.
  • composition is stable after storage for 2 months at 45°C.
  • the composition may be used for facial skincare, more particularly for treating greasy skin.

Abstract

L'invention concerne une composition comprenant, dans un milieu formant véhicule, a) un composé d'acide imidoperoxycarboxylique de formule (I): où : - A représente un cycle benzène éventuellement substitué, - R représente un atome d'hydrogène, un groupe -OH, un groupe alkyle (C1-C5), un groupe -COOH, ou un groupe -COOR1, R1 représentant un groupe alkyle (C1-C5), et - n est un nombre entier de 1 à 12, et ses sels ; b) un acide imidocarboxylique de formule (II) : où : - A' représente un cycle benzène qui est éventuellement substitué par un ou plusieurs, de préférence, jusqu'à 4, de préférence encore, par 1 ou 2 groupes choisis parmi un groupe d'alkyle (C1-C5), - m est un nombre entier de 1 à 12, et ses sels ; c ) un copolymère d'acide 2-acrylamido- 2-méthylpropanesulfonique et de (méth)acrylate d'hydroxyalkyle C2-C4, les composés (I) et (II) étant présents dans un rapport en poids composé (I)/composé (II) de 4 à 20.
PCT/EP2011/071050 2010-12-06 2011-11-25 Composition cosmétique comprenant un acide imidoperoxycarboxylique, un acide imidocarboxylique et un copolymère d'acide 2-acrylamido-2-méthyl- propanesulfonique WO2012076345A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR1060099 2010-12-06
FR1060099 2010-12-06
US42268210P 2010-12-14 2010-12-14
US61/422,682 2010-12-14

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2984121A1 (fr) * 2011-12-16 2013-06-21 Oreal Utilisation de derives acide imido-carboxylique pour diminuer la taille des pores de la peau
FR2984119A1 (fr) * 2011-12-16 2013-06-21 Oreal Composition cosmetique comprenant un acide imido-carboxylique
FR2984120A1 (fr) * 2011-12-16 2013-06-21 Oreal Utilisation de derives acide imido-carboxylique pour matifier la peau grasse
FR2984123A1 (fr) * 2011-12-19 2013-06-21 Oreal Composition cosmetique comprenant un derive d'acide imido-carboxylique sous forme solubilisee
FR2991872A1 (fr) * 2012-06-15 2013-12-20 Oreal Composition cosmetique comprenant un derive acide imido-peroxycarboxylique et un compose mono-alkyl sulfosuccinate
FR2999935A1 (fr) * 2012-12-21 2014-06-27 Oreal Utilisation de derives de l'acide imidocarboxylique pour stimuler l'activite antimicrobienne de la peau
FR2999915A1 (fr) * 2012-12-21 2014-06-27 Oreal Utilisation de derives de l'acide imidocarboxylique en tant qu'agent apaisant
FR2999914A1 (fr) * 2012-12-21 2014-06-27 Oreal Utilisation de derives de l'acide imidocarboxylique pour traiter les alterations de la peau liees a l'age ou au photovieillissement

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JPH0543894A (ja) * 1991-08-20 1993-02-23 Kao Corp 漂白剤及び漂白洗浄剤組成物
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US6471947B2 (en) 2001-01-16 2002-10-29 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Oral composition
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JPH0543894A (ja) * 1991-08-20 1993-02-23 Kao Corp 漂白剤及び漂白洗浄剤組成物
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WO2009001296A1 (fr) 2007-06-26 2008-12-31 L'oreal Utilisation cosmétique d'un dérivé d'acide imidopercaboxylique comme agent desquamant
EP2105165A2 (fr) 2008-03-28 2009-09-30 L'Oréal Composition cosmétique comprenant un dérivé d'acide imido-percarboxylique et un ester n-acylé d'acide aminé

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DATABASE WPI Week 199313, Derwent World Patents Index; AN 1993-104545, XP002649492 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2984121A1 (fr) * 2011-12-16 2013-06-21 Oreal Utilisation de derives acide imido-carboxylique pour diminuer la taille des pores de la peau
FR2984119A1 (fr) * 2011-12-16 2013-06-21 Oreal Composition cosmetique comprenant un acide imido-carboxylique
FR2984120A1 (fr) * 2011-12-16 2013-06-21 Oreal Utilisation de derives acide imido-carboxylique pour matifier la peau grasse
FR2984123A1 (fr) * 2011-12-19 2013-06-21 Oreal Composition cosmetique comprenant un derive d'acide imido-carboxylique sous forme solubilisee
FR2991872A1 (fr) * 2012-06-15 2013-12-20 Oreal Composition cosmetique comprenant un derive acide imido-peroxycarboxylique et un compose mono-alkyl sulfosuccinate
FR2999935A1 (fr) * 2012-12-21 2014-06-27 Oreal Utilisation de derives de l'acide imidocarboxylique pour stimuler l'activite antimicrobienne de la peau
FR2999915A1 (fr) * 2012-12-21 2014-06-27 Oreal Utilisation de derives de l'acide imidocarboxylique en tant qu'agent apaisant
FR2999914A1 (fr) * 2012-12-21 2014-06-27 Oreal Utilisation de derives de l'acide imidocarboxylique pour traiter les alterations de la peau liees a l'age ou au photovieillissement

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