WO2012079997A2 - Composition cosmétique comprenant un dérivé d'acide imidoperoxycarboxylique, un dérivé de sulfosuccinate de bis-alkyle et un copolymère d'acide 2-acrylamido-2-méthylpropanesulfonique - Google Patents

Composition cosmétique comprenant un dérivé d'acide imidoperoxycarboxylique, un dérivé de sulfosuccinate de bis-alkyle et un copolymère d'acide 2-acrylamido-2-méthylpropanesulfonique Download PDF

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Publication number
WO2012079997A2
WO2012079997A2 PCT/EP2011/071565 EP2011071565W WO2012079997A2 WO 2012079997 A2 WO2012079997 A2 WO 2012079997A2 EP 2011071565 W EP2011071565 W EP 2011071565W WO 2012079997 A2 WO2012079997 A2 WO 2012079997A2
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WO
WIPO (PCT)
Prior art keywords
sulphosuccinate
sodium
acid
composition according
formula
Prior art date
Application number
PCT/EP2011/071565
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English (en)
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WO2012079997A3 (fr
Inventor
Véronique Chevalier
Céline Moussay
Benoit Muller
Original Assignee
L'oreal
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Publication date
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Publication of WO2012079997A2 publication Critical patent/WO2012079997A2/fr
Publication of WO2012079997A3 publication Critical patent/WO2012079997A3/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
    • A61K8/46—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
    • A61K8/49—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
    • A61K8/8152—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
    • A61K8/81—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

Definitions

  • Cosmetic composition comprising an imidoperoxycarboxylic acid derivative a bis- alkyl sulphosuccinate derivative and a 2-acrylamido-2-methylpropanesulphonic acid copolymer
  • the invention relates to a cosmetic composition comprising an imidoperoxycarboxylic acid derivative, a bis-alkyl sulphosuccinate derivative and a 2-acrylamido-2-methyl- propanesulphonic acid copolymer. It also relates to a cosmetic treatment process for the skin using said composition.
  • 6-Phthalimidoperoxyhexanoic acid is a compound sold by the company Solvay as a deodorizing, bacteriostatic and bleaching active agent.
  • US patent 6 471 947 describes an oral cosmetic aqueous composition for whitening teeth, containing 6-phthalimidoperoxyhexanoic acid.
  • WO 2005/068470 describes aqueous compositions comprising 6-phthalimidoperoxyhexanoic acid and a nonionic surfactant.
  • 6-phthalimidoperoxyhexanoic acid Cosmetic compositions comprising 6-phthalimidoperoxyhexanoic acid are also described in documents EP-A-2 105 165 and WO 2009/001296.
  • 6-phthalimidoperoxyhexanoic acid is an active agent that is difficult to formulate in aqueous media, in particular in the conventional carriers for cosmetic compositions or detergents owing to its chemical instability: the compound degrades, the peracid being converted into an acid. This degradation causes a notable loss of activity of the compound.
  • imidoperoxycarboxylic acid derivatives can be stabilized in water when they are associated with a bis-alkyl sulphosuccinate derivative such as sodium docusate and with a 2-acrylamido-2- methylpropanesulphonic acid copolymer. Indeed, this association is stable for 2 months at 45°C.
  • the invention therefore relates to a composition
  • a composition comprising, in a physiologically acceptable aqueous medium, an imidoperoxycarboxylic acid derivative of formula (I) as defined hereinafter, a bis-alkyl sulphosuccinate derivative of formula (II) as defined hereinafter and an optionally salified copolymer of 2-acrylamido-2- methylpropanesulphonic acid and of hydroxylated C 2 -C 4 alkyl (meth)acrylate.
  • the subject of the invention is also a nontherapeutic, cosmetic treatment process for the skin, comprising the application to the skin of a composition as described above.
  • the imidoperoxycarboxylic acid derivative used in the composition according to the invention is chosen from the compounds having formula (I) below:
  • A represents a benzene ring optionally substituted with one or more, preferably up to 4, and even more preferentially with 1 or 2, groups chosen from a (d-C 5 )alkyl group,
  • R which may be identical or different, represents a hydrogen atom, an -OH group, a (CrC 5 )alkyl group, a -COOH group, or a -COOR 1 group, representing a (CrC 5 )alkyl group, and
  • n is an integer ranging from 1 to 12, for example from 1 to 8, for example from 1 to 5, or for example from 3 to 5,
  • the salts of the compounds (I) that can be used according to the invention are in particular chosen from the alkali metal salts, for example sodium or potassium salts; the alkaline earth metal salts, for example calcium, magnesium or strontium salts; the metal salts, for example zinc, aluminium, manganese or copper salts; the ammonium salts of formula NH 4 + ; the quaternary ammonium salts; the organic amine salts, for instance the methylamine, dimethylamine, trimethylamine, triethylamine, ethylamine, 2-hydroxy- ethylamine, bis(2-hydroxyethyl)amine or tris(2-hydroxyethyl)amine salts; the lysine salts and the arginine salts.
  • the salts chosen from the sodium, potassium, magnesium, strontium, copper, manganese and zinc salts are preferably used.
  • the sodium salt is used.
  • Examples of (CrC 5 )alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and pentyl.
  • R is a hydrogen atom.
  • A represents an unsubstituted benzene ring.
  • n is an integer ranging from 1 to 5.
  • the compound of formula (I) is 6-phthalimidoperoxyhexanoic acid, also known as phthalimidoperoxycaproic acid, or ⁇ -phthalimidoperoxyhexanoic acid. Its chemical structure is the following:
  • 6-Phthalimidoperoxyhexanoic acid (abbreviated to PAP) is in particular available in two commercial forms via the company Solvay.
  • 6-Phthalimidoperoxyhexanoic acid is also available in the form of an aqueous dispersion (containing 17% active material) under the trade name Eureco ® HC L17 via the company 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 using copolymers of methyl vinyl ether with maleic acid and/or anhydride, in a 1 : 1 ratio, having an alternating structure.
  • the amount of imidoperoxycarboxylic acid derivative of formula (I) to be used in a composition according to the invention depends on the desired cosmetic effect, and can therefore vary to a large extent. Those skilled in the art can readily determine the appropriate amounts on the basis of their general knowledge.
  • the imidoperoxycarboxylic acid derivative of formula (I) can be present in the composition according to the invention in a content ranging from 0.01 % to 20% by weight, relative to the total weight of the composition.
  • (I) can range from 0.05% to 15% by weight, relative to the total weight of the composition.
  • the content of said composition of formula (I) can range from 0.1 % to 10% by weight, relative to the total weight of the composition.
  • the content of said compound of formula (I) can range from 0.5% to 5% by weight, relative to the total weight of the composition.
  • composition according to the invention also comprises a bis-alkyl sulphosuccinate compound of formula (II) below:
  • Ri and R 2 which may be identical or different, denote a linear C C 20 , or linear or branched C 3 -C 2 o, alkyl radical;
  • M + represents a cation chosen from sodium, potassium, lithium or ammonium.
  • Use is preferably made of compounds (II) for which and R 2 , which may be identical or different, denote a linear C Ci 4 , or linear or branched C 3 -Ci 4 , alkyl radical.
  • R 2 which may be identical or different, denote a linear or branched C 6 -Ci 4 alkyl radical.
  • R 2 which may be identical or different, denote a linear or branched C 6 -Ci 0 alkyl radical.
  • M + represents a cation chosen from sodium, potassium and ammonium.
  • M + represents a sodium cation.
  • the bis-alkyl sulphosuccinate compound of formula (II) can be present in the composition according to the invention in a content ranging from 0.001 % to 3% by weight, relative to the total weight of the composition.
  • the content of said compound of formula (II) can range from 0.005% to 2% by weight, relative to the total weight of the composition.
  • the content of said compound of formula (II) can range from 0.01 % to 1 % by weight, relative to the total weight of the composition.
  • the content of said compound of formula (II) can range from 0.05% to 0.5% by weight, relative to the total weight of the composition.
  • the compounds (I) and (II) described above can be present in the composition according to the invention according to a compound (l)/compound (II) weight ratio ranging from 5 to 20.
  • this weight ratio ranges from 6 to 18.
  • this weight ratio ranges from 8 to 17.
  • this weight ratio ranges from 8 to 12.
  • composition according to the invention comprises an optionally salified copolymer of 2-acrylamido-2-methylpropanesulphonic acid and of hydroxylated C 2 -C 4 alkyl (meth)acrylate.
  • the hydroxylated C 2 -C 4 alkyl (meth)acrylate monomer can be chosen from 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2,3-dihydroxypropyl acrylate and 2, 3-d i hydroxy propyl methacrylate.
  • Said copolymer may be salified, in particular in the form of an alkali metal salt such as, for example, the sodium or potassium salt, or in the form of an ammonium salt, or in the form of a salt of an amino alcohol, such as, for example, the monoethanolamine salt, or in the form of an amino acid salt, such as, for example, the lysine salt.
  • an alkali metal salt such as, for example, the sodium or potassium salt
  • an ammonium salt or in the form of a salt of an amino alcohol, such as, for example, the monoethanolamine salt
  • an amino acid salt such as, for example, the lysine salt.
  • the copolymer is salified in sodium salt form.
  • the composition comprises the copolymer of 2-acrylamido-2- methylpropanesulphonic acid and of 2-hydroxyethyl acrylate, in particular in sodium salt form, for instance those sold under the trade names Sepinov ® EMT 10 or Simulgel ® NS by the company SEPPIC (I NCI name: hydroxyethyl acrylate/sodium acryloyldimethyl taurate copolymer) .
  • Such polymers are in particular described in application FR-A-2856691.
  • the copolymer of 2-acrylamido-2-methylpropanesulphonic acid and of hydroxylated C 2 -C 4 alkyl (meth)acrylate can be present in the composition according to the invention in a content ranging from 0.05% to 20% by weight, relative to the total weight of the composition.
  • the content of said copolymer can range from 0.1 % to 10% by weight, relative to the total weight of the composition.
  • the content of said copolymer can range from 0.5% to 5% by weight, relative to the total weight of the composition.
  • the imidoperoxycarboxylic acid derivative of formula (I) (termed A) and the copolymer of 2-acrylamido-2-methylpropanesulphonic acid and of hydroxylated C 2 -C 4 alkyl (meth)acrylate (termed B) can be present in the composition according to the invention according to an A/B weight ratio ranging from 1/5 to 5/1.
  • this A/B weight ratio can range from 1/3 to 3/1.
  • this A/B weight ratio can range from 0.4 to 1.1. More preferentially, this A/B weight ratio can range from 0.5 to 1.
  • composition according to the invention comprises a physiologically acceptable aqueous medium, i.e. an aqueous medium which is nontoxic, which is capable of being applied to human keratin materials, and which has a pleasant appearance, odour and feel.
  • a physiologically acceptable aqueous medium i.e. an aqueous medium which is nontoxic, which is capable of being applied to human keratin materials, and which has a pleasant appearance, odour and feel.
  • the composition is in particular a cosmetic composition.
  • the composition according to the invention comprises water, for example in a content ranging from 50% to 99% by weight, relative to the total weight of the composition.
  • the water content in the composition can range from 60% to 97% by weight.
  • composition according to the invention has a pH included in the range of from 3 to 5.
  • the pH of the composition ranges from 3.5 to 4.2.
  • the pH of the composition can be adjusted, for example, using sodium hydroxide, citric acid, sodium citrate, potassium citrate, lactic acid, sodium lactate, potassium lactate, glycolic acid, sodium glycolate or potassium glycolate.
  • the composition can comprise at least one oil in particular chosen from linear or branched C 6 -Ci 5 alkanes, linear or cyclic polydimethylsiloxane silicone oils having from 2 to 7 silicon atoms, such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexa- siloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane or dodecamethylpentasiloxane, polydimethylsiloxanes (and preferably those with a viscosity less than 200 cSt), and fatty acid triglycerides, in particular capric/caprylic acid triglycerides (such as those sold under the name Miglyol 812 N by the company Sasol or Myritol 318 by the company Cognis).
  • the oil can be present in the composition according to the invention in a content ranging from 0.05% to 50% by weight, relative to the total weight of the composition.
  • said oil can be present in a content ranging from 0.1 % to 30% by weight, relative to the total weight of the composition.
  • said oil can be present in a content ranging from 1 % to 20% by weight, relative to the total weight of the composition.
  • composition according to the invention can also contain a cosmetic active agent which is stable at acid pH. It can contain an active agent chosen from:
  • composition can also comprise other cosmetic additives, provided that the good stability of the compound of formula (I) is maintained.
  • cosmetic additives mention may, for example, be made of xanthan gum and the polyvinyl methyl ether)/maleic acid copolymer (such as, for example, the product sold under the name Gantrez ® S-97 BF by the company ISP).
  • composition according to the invention can be in the form of an aqueous gel or of an oil-in-water (O/W) emulsion. It is in particular intended to be applied topically to the skin.
  • O/W oil-in-water
  • the invention also relates to a nontherapeutic, cosmetic treatment process for the skin, comprising the application, to the skin, of a composition as described above.
  • the cosmetic treatment process concerns the treatment of oily skin and the composition is applied to oily skin.
  • the composition is applied to the facial zone, in particular the T-zone (forehead, nose, cheeks, chin), in particular the cheeks and the nose.
  • T-zone forehead, nose, cheeks, chin
  • the peroxide number is the amount of product (acid A) present in the sample, expressed in milliequivalents of active oxygen per kilogram, which oxidizes the potassium iodide.
  • Gels 2 and 3 according to the invention exhibit good stability at 2 months at 45°C: the 6-phthalimidoperoxyhexanoic acid content is greater than that of gel 1 which is not part of the invention.
  • composition applied to the face makes it possible to treat oily skin.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne une composition qui comprend, dans un milieu aqueux physiologiquement acceptable, un composé d'acide imidoperoxycarboxylique de formule (I) ci-dessous : dans laquelle : - A représente un cycle benzène éventuellement substitué, - R représente un atome d'hydrogène, un groupe -OH, un groupe alkyle en C1-C5, un groupe -COOH ou un groupe -COOR1, R1 représentant un groupe alkyle en C1-C5, et - n est un entier allant de 1 à 12, et ses sels ; et un composé de sulfosuccinate de bis-alkyle de formule (II) ci-dessous, dans laquelle : R1 et R2, qui peuvent être identiques ou différents, représentent un radical alkyle linéaire en C1-C20 ou linéaire ou ramifié en C3-C20 ; M+ représente un cation choisi parmi le sodium, le potassium, le lithium ou l'ammonium, et un copolymère éventuellement salifié d'acide 2-acrylamido-2-méthylpropanesulfonique et de (méth)acrylate d'alkyle en C2-C4 hydroxylé. L'invention concerne également son utilisation pour le traitement de la peau grasse.
PCT/EP2011/071565 2010-12-17 2011-12-01 Composition cosmétique comprenant un dérivé d'acide imidoperoxycarboxylique, un dérivé de sulfosuccinate de bis-alkyle et un copolymère d'acide 2-acrylamido-2-méthylpropanesulfonique WO2012079997A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR1060706A FR2968958B1 (fr) 2010-12-17 2010-12-17 Composition cosmetique comprenant un derive acide imido-peroxycarboxylique et un compose bis-akyl sulfosuccinate
FR1060706 2010-12-17
US201061425261P 2010-12-21 2010-12-21
US61/425,261 2010-12-21

Publications (2)

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WO2012079997A2 true WO2012079997A2 (fr) 2012-06-21
WO2012079997A3 WO2012079997A3 (fr) 2014-01-23

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2991872A1 (fr) * 2012-06-15 2013-12-20 Oreal Composition cosmetique comprenant un derive acide imido-peroxycarboxylique et un compose mono-alkyl sulfosuccinate

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1074607A1 (fr) 1999-08-04 2001-02-07 Ausimont S.p.A. Dispersions aqueuses d'acides percarboxyliques
US6471947B2 (en) 2001-01-16 2002-10-29 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Oral composition
FR2856691A1 (fr) 2003-06-26 2004-12-31 Seppic Sa Nouveau polymere en poudre, procede pour sa preparation et utilisation comme epaississant
WO2005068470A2 (fr) 2004-01-08 2005-07-28 Solvay Solexis S.P.A. Formulations aqueuses d'acides imido-alcane-percarboxyliques
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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Publication number Priority date Publication date Assignee Title
IT1293820B1 (it) * 1997-08-05 1999-03-10 Ausimont Spa Composizioni a base di perossiacidi
US6013637A (en) * 1998-06-12 2000-01-11 Dermik Laboratories Inc. Anti-acne method and composition
ATE392465T1 (de) * 2005-04-27 2008-05-15 Mifa Ag Frenkendorf Flüssigwaschmittel mit bleichmittelzusatz
US7994112B2 (en) * 2009-01-26 2011-08-09 Procter & Gamble Comany Fabric softening laundry detergent

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1074607A1 (fr) 1999-08-04 2001-02-07 Ausimont S.p.A. Dispersions aqueuses d'acides percarboxyliques
US6471947B2 (en) 2001-01-16 2002-10-29 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Oral composition
FR2856691A1 (fr) 2003-06-26 2004-12-31 Seppic Sa Nouveau polymere en poudre, procede pour sa preparation et utilisation comme epaississant
WO2005068470A2 (fr) 2004-01-08 2005-07-28 Solvay Solexis S.P.A. Formulations aqueuses d'acides imido-alcane-percarboxyliques
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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2991872A1 (fr) * 2012-06-15 2013-12-20 Oreal Composition cosmetique comprenant un derive acide imido-peroxycarboxylique et un compose mono-alkyl sulfosuccinate

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WO2012079997A3 (fr) 2014-01-23
FR2968958B1 (fr) 2015-06-26

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