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WO2012079997A2 - Cosmetic composition comprising an imidoperoxycarboxylic acid derivative a bis-alkyl sulphosuccinate derivative and a 2-acrylamido-2-methylpropanesulphonic acid copolymer - Google Patents

Cosmetic composition comprising an imidoperoxycarboxylic acid derivative a bis-alkyl sulphosuccinate derivative and a 2-acrylamido-2-methylpropanesulphonic acid copolymer 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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Prior art keywords
sulphosuccinate
sodium
acid
composition according
formula
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PCT/EP2011/071565
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French (fr)
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WO2012079997A3 (en
Inventor
Véronique Chevalier
Céline Moussay
Benoit Muller
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LOreal SA
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LOreal SA
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913Cosmetics 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
    • A61K8/492Cosmetics 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141Compositions 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
    • A61K8/8152Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141Compositions 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
    • A61K8/8158Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/008Preparations 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)
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  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

The invention relates to a composition comprising, in a physiologically acceptable aqueous medium, an imidoperoxycarboxyiic acid compound of formula (I) below: in which: - A represents an optionally substituted benzene ring, - R represents a hydrogen atom, an -OH group, a (C1-C5)alkyl group, a -COOH group or a -COOR1 group, R1 representing a (C1-C5)alkyl group, and - n is an integer ranging from 1 to 12, and salts thereof; and a bis-alkyl sulphosuccinate compound of formula (II) below, in which: R1 and R2, which may be identical or different, denote a linear C1-C20, or linear or branched C3-C20, alkyl radical; M+ represents a cation chosen from sodium, potassium, lithium or ammonium, and an optionally salified copolymer of 2-acrylamido-2-methylpropanesulphonic acid and of hydroxylated C2-C4 alkyl (meth)acrylate. Use in the treatment of oily skin.

Description

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.
Application WO 2005/068470 describes aqueous compositions comprising 6-phthalimidoperoxyhexanoic acid and a nonionic surfactant.
Cosmetic compositions comprising 6-phthalimidoperoxyhexanoic acid are also described in documents EP-A-2 105 165 and WO 2009/001296. However, 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.
As it happens, the applicant has just demonstrated that 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 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 C2-C4 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:
Figure imgf000003_0001
in which:
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-C5)alkyl group,
R, which may be identical or different, represents a hydrogen atom, an -OH group, a (CrC5)alkyl group, a -COOH group, or a -COOR1 group, representing a (CrC5)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,
and salts thereof.
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 NH4 +; 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. Preferentially, the sodium salt is used.
Examples of (CrC5)alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and pentyl.
According to one embodiment, an imido-aromatic percarboxylic acid derivative of formula (I), for which A is an unsubstituted benzene ring, R is a hydrogen atom, a -COOH group or a (CrC3)alkyl group, and n ranges from 1 to 5, is used. Preferably, R is a hydrogen atom.
Preferably, A represents an unsubstituted benzene ring.
Preferably, n is an integer ranging from 1 to 5.
Among the compounds of formula (I), mention may be made of phthalimidoperoxyacetic acid (A = benzene; R = H; n = 1), 2-phthalimidoperoxypropionic acid, 3-phthalimido- peroxypropionic acid (A = benzene; R = H; n = 2), 4-phthalimidoperoxybutanoic acid, 3-phthalimidoperoxybutanoic acid, phthalimidoperoxypentanoic acid, phthalimido- peroxyhexanoic acid, phthalimidoperoxyheptanoic acid, phthalimidoperoxyoctanoic acid, phthalimidoperoxynonanoic acid, phthalimidoperoxydecanoic acid, phthalimido- peroxyundecanoic acid, phthalimidoperoxydodecanoic acid and 2-phthalimidomono- peroxysuccinic acid.
Preferably, the compound of formula (I) is 6-phthalimidoperoxyhexanoic acid, also known as phthalimidoperoxycaproic acid, or ε-phthalimidoperoxyhexanoic acid. Its chemical structure is the following:
Figure imgf000004_0001
It corresponds to a compound for formula (I) in which R represents a hydrogen atom, A represents an unsubstituted benzene ring and n = 5. Its I NCI name is: phthalimidoperoxycaproic acid.
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. Preferably, the content of said compound of formula
(I) can range from 0.05% to 15% by weight, relative to the total weight of the composition.
In particular, 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.
Preferentially, 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.
The composition according to the invention also comprises a bis-alkyl sulphosuccinate compound of formula (II) below:
FL 2OOC— ChL 2— C I H— COOR, 1 M (II)
SO, in which:
Ri and R2, which may be identical or different, denote a linear C C20, or linear or branched C3-C2o, alkyl radical;
M+ represents a cation chosen from sodium, potassium, lithium or ammonium.
In the compounds of formula (II) as alkyl groups, mention may in particular be made of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-octyl, 2-ethylhexyl, dodecyl and hexadecyl groups.
Use is preferably made of compounds (II) for which and R2, which may be identical or different, denote a linear C Ci4, or linear or branched C3-Ci4, alkyl radical. Preferentially, use is made of compounds (II) for which and R2, which may be identical or different, denote a linear or branched C6-Ci4 alkyl radical.
More preferentially, use is made of compounds (II) for which and R2, which may be identical or different, denote a linear or branched C6-Ci0 alkyl radical.
Advantageously, M+ represents a cation chosen from sodium, potassium and ammonium. Preferably, M+ represents a sodium cation.
As examples of compounds (II), mention may be made of:
Figure imgf000006_0001
Sodium di(1 ,3- dimethylbutyl)
1 ,3- 1 ,3-
1 2373-38-8 sulphosuccinate Na dimethylbutyl dimethylbutyl
(Aerosol MA 80
from Cytec)
Sodium dioctyl
sulphosuccinate
J 1639-66-3 n-octyl n-octyl Na
(Texapon DOS
from Cognis)
Sodium dipentyl
sulphosuccinate
K 922-80-5 n-pentyl n-pentyl Na
(Aerosol AY from
Cytec)
Sodium
diethylhexyl
577-11 -7
L sulphosuccinate 2-ethylhexyl 2-ethylhexyl Na
(Aerosol OT from
Cytec)
Sodium diisobutyl
sulphosuccinate
M 127-39-9 2-methylpropyl 2-methylpropyl Na
(Monawet MB 100
from Akzonobel)
Potassium di¬
N 7491 -09-0 ethylhexyl) 2-ethylhexyl 2-ethylhexyl K sulphosuccinate
Ammonium didecyl
0 94313-89-0 decyl decyl NH4 sulphosuccinate
Ammonium di(2-
P 30673-56-4 ethylhexyl) 2-ethylhexyl 2-ethylhexyl NH4 sulphosuccinate
Ammonium dinonyl
Q 27501 -55-9 nonyl nonyl NH4 sulphosuccinate
Ammonium
R 2160-35-2 ditridecyl tri decyl tri decyl NH4 sulphosuccinate
Among the compounds of formula (II), use will more particularly be made of the compounds (J) or (L) which have the following chemical structures:
Figure imgf000007_0001
Figure imgf000008_0001
(L)
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. Preferably, 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. In particular, 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.
Preferentially, 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.
Advantageously, 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.
Advantageously, this weight ratio ranges from 6 to 18.
Preferably, this weight ratio ranges from 8 to 17.
Preferentially, this weight ratio ranges from 8 to 12.
The composition according to the invention comprises an optionally salified copolymer of 2-acrylamido-2-methylpropanesulphonic acid and of hydroxylated C2-C4 alkyl (meth)acrylate.
Such a copolymer reinforces the stability of the compounds by maintaining them in suspension in water and by avoiding chemical degradation thereof over time. The hydroxylated C2-C4 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.
Advantageously, the copolymer is salified in sodium salt form. Preferably, 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 C2-C4 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. Preferably, the content of said copolymer can range from 0.1 % to 10% by weight, relative to the total weight of the composition.
Preferentially, the content of said copolymer can range from 0.5% to 5% by weight, relative to the total weight of the composition.
Advantageously, the imidoperoxycarboxylic acid derivative of formula (I) (termed A) and the copolymer of 2-acrylamido-2-methylpropanesulphonic acid and of hydroxylated C2-C4 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. Preferably, this A/B weight ratio can range from 1/3 to 3/1. Preferentially, 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.
The 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.
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. Preferably, the water content in the composition can range from 60% to 97% by weight.
Advantageously, the composition according to the invention has a pH included in the range of from 3 to 5.
Preferably, 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. According to one embodiment of the invention, the composition can comprise at least one oil in particular chosen from linear or branched C6-Ci5 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. Preferably, said oil can be present in a content ranging from 0.1 % to 30% by weight, relative to the total weight of the composition. Preferentially, said oil can be present in a content ranging from 1 % to 20% by weight, relative to the total weight of the composition.
The 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:
ascorbic acid, kojic acid, caffeic acid, salicylic acid and its derivatives, citric acid, lactic acid, methyllactic acid, glucuronic acid, glycolic acid, pyruvic acid, 2-hydroxybutanoic acid, 2-hydroxypentanoic acid, 2-hydroxyhexanoic acid, 2-hydroxyheptanoic acid, 2-hydroxyoctanoic acid, 2-hydroxynonanoic acid, 2-hydroxydecanoic acid, 2-hydroxy- undecanoic acid, 2-hydroxydodecanoic acid, 2-hydroxytetradecanoic acid, 2-hydroxy- hexadecanoic acid, 2-hydroxyoctadecanoic acid, 2-hydroxytetracosanoic acid, 2-hydroxy- eicosanoic acid, mandelic acid, benzoic acid, phenyllactic acid, gluconic acid, galacturonic acid, aleuritic acid, ribonic acid, tartronic acid, tartaric acid, maleic acid, fumaric acid, retinoic acid and its derivatives, benzene-1 ,4-di(3-methylidene-10-camphor- sulphonic acid, urocanic acid, 2-phenylbenzimidazole-5-sulphonic acid, oc-(oxo-2- bornylidene-3-)-toluene-4-sulphonic acid, 2-hydroxy-4-methoxy-5-sulphonic acid, plant extracts containing acids and more especially fruit extracts, acidic xanthine derivatives, β-glycyrrhetinic acid and asiatic acid, and mixtures thereof. The composition can also comprise other cosmetic additives, provided that the good stability of the compound of formula (I) is maintained. As 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).
The 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.
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. In particular, the cosmetic treatment process concerns the treatment of oily skin and the composition is applied to oily skin.
According to one particular embodiment, the composition is applied to the facial zone, in particular the T-zone (forehead, nose, cheeks, chin), in particular the cheeks and the nose.
The invention is illustrated in the examples which follow.
COMPARATIVE EXAMPLES 1 TO 3
2 aqueous gels according to the invention (gels 2, 3) and one aqueous gel which is not part of the invention (gel 1) having the following compositions were prepared:
(The amounts are expressed as percentage by weight)
Gel:
- 6-phthalimidoperoxyhexanoic acid in an aqueous dispersion
containing 17% AM (Eureco HC L17® from Solvay) 1.70% AM, i.e. 10% as it is - Monosodium salt of di(2-ethylhexyl) sulphosuccinate
(Aerosol OT from Cytec) X% AM
- Sodium 2-acrylamido-2-methylpropanesulphonate/
2-hydroxyethyl methacrylate copolymer at 90% in water
(Sepinov EMT 10 from SEPPIC) 1.8% AM, i.e. 2% as it is - Sodium hydroxide 0.008%
- Water qs 100% The stability of each gel was evaluated after 2 months of storage at 45°C by measuring the content of 6-phthalimidoperoxyhexanoic acid (acid A). The assay is carried out by measuring the peroxide number according to standard NFT 60-220; a test sample dissolved in acetic acid and chloroform is treated with a solution of potassium iodide, and the iodine released is titrated with a titred solution of sodium thiosulphate.
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. The following results were obtained:
Figure imgf000012_0001
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.
The composition of gels 2 and 3, applied to oily skin, makes it possible to treat said skin. Example 4:
The following composition was prepared:
- 6-phthalimidoperoxyhexanoic acid in an aqueous dispersion
containing 17% AM (Eureco HC L17® from Solvay) 1.70% AM, i.e. 10% as it is
- Monosodium salt of di(2-ethylhexyl) sulphosuccinate
(Aerosol OT from Cytec) 0.1 % AM
- Sodium 2-acrylamido-2-methylpropanesulphonate/
2-hydroxyethyl methacrylate copolymer at 90% in water
(Sepinov EMT 10 from SEPPIC) 1.8% AM, i.e. 2% as it is - Capric/caprylic acid triglycerides
(Miglyol 812 N from the company Sasol) 5%
- Water qs 100% The composition is stable after storage for 2 months at 45°C.
The composition applied to the face makes it possible to treat oily skin.

Claims

Composition comprising, in a physiologically acceptable aqueous medium, an imidoperoxycarboxylic acid compound of formula (I) below:
Figure imgf000014_0001
in which:
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-C5)alkyl group, - R, which may be identical or different, represents a hydrogen atom, an -OH group, a (CrC5)alkyl group, a -COOH group or a -COOR1 group, representing a (CrC5)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,
and salts thereof; b) a bis-alkyl sulphosuccinate compound of formula (II) below:
FL 2OOC— ChL 2— C I H— COOR, 1 M (II)
SO,
in which:
R and R2, which may be identical or different, denote a linear C C2o, or linear or branched C3-C20, alkyl radical;
M+ represents a cation chosen from sodium, potassium, lithium or ammonium, and c) an optionally salified copolymer of 2-acrylamido-2-methylpropanesulphonic acid and of hydroxylated C2-C4 alkyl (meth)acrylate.
2. Composition according to the preceding claim, characterized in that, for the compound of formula (I), A is an unsubstituted benzene ring, R is a hydrogen atom, a -COOH group or a (CrC3)alkyl group, and n ranges from 3 to 5.
3. Composition according to either one of the preceding claims, characterized in that the compound of formula (I) is 6-phthalimidoperoxyhexanoic acid.
4. Composition according to any one of the preceding claims, characterized in that the compound of formula (I) is present in a content ranging from 0.01 % to 20% by weight, relative to the total weight of the composition, preferably ranging from 0.05% to 15% by weight, preferentially ranging from 0.1 % to 10% by weight, and more preferentially ranging from 0.5% to 5% by weight.
5. Composition according to any one of the preceding claims, characterized in that, for the compound of formula (II):
and R2, which may be identical or different, denote a linear or branched C6-Ci4 alkyl radical;
M+ represents a cation chosen from sodium, potassium and ammonium.
6. Composition according to any one of the preceding claims, characterized in that the compound of formula (II) is chosen from
sodium dihexyl sulphosuccinate;
sodium di(2,6-dimethylheptyl) sulphosuccinate;
sodium di(l -methylpentyl) sulphosuccinate;
sodium dibutyl sulphosuccinate;
sodium didodecyl sulphosuccinate;
sodium dinonyl sulphosuccinate;
sodium dihexyl sulphosuccinate;
sodium ditridecyl sulphosuccinate;
sodium di(1 ,3-dimethylbutyl) sulphosuccinate;
sodium dioctyl sulphosuccinate;
sodium dipentyl sulphosuccinate;
sodium diethylhexyl sulphosuccinate;
sodium diisobutyl sulphosuccinate;
potassium di(2-ethylhexyl) sulphosuccinate;
ammonium didecyl sulphosuccinate;
ammonium di(2-ethylhexyl) sulphosuccinate;
ammonium dinonyl sulphosuccinate;
ammonium ditridecyl sulphosuccinate.
7. Composition according to any one of the preceding claims, characterized in that the compound of formula (II) is chosen from sodium dioctyl sulphosuccinate and sodium diethylhexyl sulphosuccinate.
8. Composition according to any one of the preceding claims, characterized in that the compound of formula (II) is present in a content ranging from 0.001 % to 3% by weight, relative to the total weight of the composition, preferably ranging from 0.005% to 2% by weight, preferentially ranging from 0.01 % to 1 % by weight, and more preferentially ranging from 0.05% to 0.5% by weight.
9. Composition according to any one of the preceding claims, characterized in that it comprises an optionally salified copolymer of 2-acrylamido-2-methylpropanesulphonic acid and of 2-hydroxyethyl acrylate.
10. Composition according to any one of the preceding claims, characterized in that it has a pH included in the range of from 3 to 5.
1 1 . Composition according to any one of the preceding claims, characterized in that it comprises at least one oil chosen from linear or branched C6-Ci5 alkanes, linear or cyclic polydimethylsiloxane silicone oils having from 2 to 7 silicon atoms, polydimethylsiloxanes, and capric/caprylic acid triglycerides.
12. Nontherapeutic, cosmetic treatment process for the skin, comprising the application, to the skin, of a composition according to any one of the preceding claims.
13. Nontherapeutic, cosmetic treatment process for oily skin, comprising the application, to oily skin, of a composition according to any one of Claims 1 to 1 1.
PCT/EP2011/071565 2010-12-17 2011-12-01 Cosmetic composition comprising an imidoperoxycarboxylic acid derivative a bis-alkyl sulphosuccinate derivative and a 2-acrylamido-2-methylpropanesulphonic acid copolymer Ceased WO2012079997A2 (en)

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