WO2011114009A1 - Cosmetic composition comprising an imidoperoxycarboxylic acid derivative and a 2-acrylamido-2-methylpropanesulphonic acid copolymer - Google Patents

Abstract

The invention relates to a composition comprising, in a physiologically acceptable aqueous medium, an imidoperoxycarboxylic acid compound having the following formula (I): in which: - A is an optionally substituted benzene ring - R is a hydrogen atom, an -OH group, a (C₁-C₅)alkyl group, a -COOH group or a -COOR₁ group, R₁ being a (C₁-C₅)alkyl group, and - n is an integer ranging from 1 to 5, and salts thereof; and a 2-acrylamido-2-methylpropanesulphonic acid/hydroxylated C₂-C₄ alkyl (meth)acrylate copolymer. Use in the treatment of oily skin.

Description

 Cosmetic composition comprising an imido-peroxycarboxylic acid derivative and a 2-acrylamido-2-methylpropanesulfonic acid copolymer.

The invention relates to a cosmetic composition comprising an imidoperoxycarboxylic acid derivative and a 2-acrylamido-2-methylpropanesulfonic acid copolymer. It also relates to a method of cosmetic treatment of the skin using said composition.

6-Phthalimidoperoxyhexanoic acid is a compound marketed by SOLVAY as a deodorant, bacteriostatic and decolorizing active agent.

US Pat. No. 6,471,947 discloses a cosmetic oral cosmetic composition for bleaching teeth containing 6-phthalimidoperoxyhexanoic acid.

WO 2005/068470 discloses aqueous compositions comprising 6-phthalimidoperoxyhexanoic acid and a nonionic surfactant.

 Cosmetic compositions comprising 6-phthalimidoperoxyhexanoic acid are also described in EP-A-2105165 and WO 2009/001296.

However, 6-phthalimidoperoxyhexanoic acid is an asset that is difficult to formulate in conventional carriers of cosmetic compositions because of its chemical instability: the compound degrades, the peracid being converted into acid. This degradation causes a significant loss of activity of the compound.

Now the Applicant has just demonstrated that the imidoperoxycarboxylic acid derivatives could be kept in suspension in water and stably for 2 months at 45 ° C when combined with a particular copolymer of 2-acrylamido acid -2-methylpropane-sulfonic acid. This maintenance in suspension in water makes it possible to keep a good stability of the compounds while avoiding their chemical degradation over time.

The invention therefore relates to a composition comprising, in a physiologically acceptable aqueous medium, an imido-peroxycarboxylic acid derivative as defined below and a copolymer of 2-acrylamido-2-methylpropanesulfonic acid and neutral monomer such as as defined below. The subject of the invention is also a process for the cosmetic, non-therapeutic treatment of the skin comprising the application to the skin of a composition as described above. The imido-peroxycarboxylic acid derivative used in the composition according to the invention is chosen from the compounds of formula (I) below:

in which :

A represents a benzene ring optionally substituted with one or more, preferably up to 4, and even more preferably with 1 or 2 groups chosen from a (C ₁ -C ₅ ) alkyl group,

R, identical or different, represents a hydrogen atom, an -OH group, a (C ₁ -C ₅ ) alkyl group, a -COOH group, a -COOR ₁ group, R ₁ representing a (C ₁ -C ₅ ) alkyl group, and

 n is an integer ranging from 1 to 5, for example from 1 to 3 or for example from 3 to 5, and their salts.

The salts of the compounds that may be used according to the invention are in particular chosen from alkali metal salts, for example sodium and potassium; alkaline earth metal salts, for example calcium, magnesium, strontium, metal salts, for example zinc, aluminum, manganese, copper; ammonium salts of formula NH ₄ ⁺ ; quaternary ammonium salts; organic amine salts, such as for example the salts of methylamine, dimethylamine, trimethylamine, triethylamine, ethylamine, 2-hydroxyethylamine, bis- (2-hydroxyethyl) amine, tri- (2- hydroxyethyl) amine; lysine salts, arginine. Salts chosen from among the sodium, potassium, magnesium, strontium, copper, manganese and zinc salts are preferably used. Preferably, the sodium salt is used. Examples of (C ₁ -C ₅ ) alkyl groups are methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, and pentyl.

According to one embodiment, an imido-aromatic percarboxylic acid derivative of formula (I) is used, 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 3 to 5.

Preferably, R is a hydrogen atom.

Preferably, A represents an unsubstituted benzene ring.

Among the compounds of formula (I), mention may be made of phthalimido-peroxyacetic acid

(A = benzene, R = H, n = 1), 2-phthalimido-peroxy-propionic acid, the acid

3-phthalimido-peroxypropionic acid (A = benzene, R = H; n = 2), 4-phthalimidoperoxybutanoic acid, 3-phthalimidoperoxybutanoic acid, phthalimidoperoxypentanoic acid, phthalimidoperoxyhexanoic acid, phthalimidoperoxyhexanoic acid, phthalimidoperoxyheptanoic acid, phthalimidoperoxyoctanoic acid, phthalimidoperoxynonanoic acid, phthalimidoperoxydecanoic acid, phthalimidoperoxyundecanoic acid, phthalimidoperoxydodecanoic acid, 2-phthalimido-mono-peroxysuccinic acid.

Preferably, the compound of formula (I) is phthalimidoperoxyhexanoic acid, also called phthalimidoperoxycaproic acid, ε-phthalimidoperoxyhexanoic acid. Its chemical structure is as follows:

 It corresponds to a compound of formula (I) in which R represents a hydrogen atom, A represents an unsubstituted benzene ring and n = 5. It is called INCI: phthalimidoperoxycaproic acid. 6-Phthalimidoperoxyhexanoic acid (abbreviated as PAP) is in particular available in two commercial forms by SOLVAY.

The 6-phthalimidopéroxyhexanoïque acid is also available as an aqueous dispersion (17% active material) under the trade name EURECO ^® HC L17 by the company Solvay.

The 6-phthalimidopéroxyhexanoïque acid is also provided in the form of a powder under the tradename EURECO ^® HC-P1 1. Aqueous dispersions of 6-phthalimidoperoxyhexanoic acid are described in EP 1 074 607. These aqueous dispersions are stabilized by copolymers of methyl vinyl ether with maleic acid and / or maleic anhydride in a 1: 1 ratio. having an alternating structure.

The amount of imido-peroxycarboxylic 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 easily, on the basis of their general knowledge, determine the appropriate quantities.

The imido-peroxycarboxylic acid derivative of formula (I) may be present in the composition according to the invention in a content ranging from 0.0001% to 30% by weight, relative to the total weight of the composition. Preferably, the content of said compound of formula (I) can range from 0.001% to 20% by weight, relative to the total weight of the composition. In particular, the content of said compound of formula (I) can range from 0.01% to 20% by weight, relative to the total weight of the composition.

 Preferably, the content of said compound of formula (I) may range from 0.05% to 5% by weight, relative to the total weight of the composition. The composition according to the invention comprises a copolymer of 2-acrylamido-2-methylpropanesulfonic acid and hydroxylated (C 2 -C 4) alkyl (meth) acrylate, optionally salified.

The C2-C4 alkyl (meth) acrylate hydroxyl monomer may be chosen from 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2,3-dihydroxypropyl acrylate, 2,3-methacrylate and 2,3-dihydroxypropyl acrylate. -dihydroxypropyle.

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 aminoalcohol such as, for example, salt monoethanolamine, or in the form of an amino acid salt such as, for example, the lysine salt.

Advantageously, the copolymer is salified in the form of sodium salt.

Preferably, the composition comprises the copolymer of 2-acrylamido-2-methylpropanesulphonic acid and of 2-hydroxyethyl acrylate, especially in the form of sodium salt, for example those sold under the trade names "Sepinov ^® EMT 10" or "SIMULGEL ^® NS" by Seppic (INCI name: Hydroxyethyl Acrylate / Sodium acryloyldimethyltaurate copolymer).

Such polymers are described in application FR-A-2856691.

The copolymer of 2-acrylamido-2-methylpropanesulfonic acid and of C2-C4 alkyl (meth) acrylate hydroxylated may 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 may range from 0.1% to 10% by weight, relative to the total weight of the composition.

 Preferably, the content of said copolymer may range from 0.5% to 5% by weight, relative to the total weight of the composition.

Advantageously, the imido-peroxycarboxylic acid derivative of formula (I) (referred to as A) and the copolymer of 2-acrylamido-2-methylpropanesulfonic acid and of C2-C4 alkyl (meth) acrylate hydroxylated (said B) may be present in the composition according to the invention in a weight ratio A / B ranging from 1/5 to 5/1. Preferably, this A / B weight ratio can range from 1/3 to 3/1. Preferably, this weight ratio A / B may range from 0.4 to 1.1. More preferably, this weight ratio A / B can range from 0.5 to 1.

The composition according to the invention comprises a physiologically acceptable aqueous medium, ie a non-toxic aqueous medium that can be applied to human keratin materials and has a pleasant appearance, odor 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 may range from 60% to 97% by weight. Advantageously, the composition according to the invention has a pH ranging from 3 to 5.

Preferably, the pH of the composition ranges from 3.5 to 4.2.

The pH of the composition may be adjusted, for example, with sodium hydroxide, citric acid of sodium citrate, potassium citrate, lactic acid, sodium lactate, potassium lactate or glycolic acid. , sodium glycolate, potassium glycolate. According to one embodiment of the invention, the composition may comprise at least one oil chosen from linear or branched C 8 -C 15 alkanes, linear or cyclic polydimethylsiloxane silicone oils having from 2 to 7 silicon atoms such as that octamethyl cyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, hexamethyl disiloxane, octamethylsiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, polydimethylsiloxanes (and preferably those of viscosity less than 200), triglycerides of capric / caprylic acids (such as those sold under the name MIGLYOL 812 N by the company SASOL or MYRITOL 318 by the company COGNIS).

The oil may 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 may be present in a content ranging from 0.1% to 30% by weight, relative to the total weight of the composition. Preferably, said oil may 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 may further contain a stable cosmetic active at acidic pH. It may contain an asset 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-hydroxy-butanoic acid, 2-hydroxypentanoic acid, 2-hydroxyhexanoic acid, 2-hydroxyheptanoic acid, 2-hydroxyoctanoic acid, 2-hydroxy-nonanoic acid, 2-hydroxydecanoic acid, 2-hydroxyundecanoic acid, 2-hydroxydodecanoic acid, 2-hydroxy-tetradecanoic acid, 2-hydroxy-hexadecanoic acid, 2-hydroxy-octadecanoic acid, acid 2-hydroxytetra-cosanoic acid, 2-hydroxy-eicosanoic acid, mandelic acid, benzoic acid, phenyllactic acid, gluconic acid, galacturonic acid, aleuritic acid, ribonic acid, tartaric acid, tartaric acid, malic acid, fumaric acid, retinoic acid and its derivatives, benzene-1,4-di (3-methylidene 10-camphosulfoic acid) urocanic acid, 2-phenyl benzimidazole 5-sulphonic acid, α- (2-oxo-2-bornylidene) toluene-4-sulfonic acid, 2-hydroxy-4-methoxy-5-acid - sulphonic acid, vegetable extracts containing acids and more especially extracts fruit, acid xanthic derivatives, β-glycyrrhetinic acid, Asian acid and mixtures thereof.

The composition may also comprise other cosmetic additives, provided that the stability of the compound of formula (I) is maintained. As cosmetic additives can for example be made of xanthan gum, polyvinyl methyl ether / maleic acid copolymer (such as that sold under the name Gantrez ^® S-97 BF by ISP) The composition according to the invention can be present as an aqueous gel or oil-in-water (O / W) emulsion. It is especially intended to be applied topically to the skin.

The invention also relates to a non-therapeutic cosmetic method for treating the skin, comprising the application to the skin of a composition as described above. In particular, the cosmetic treatment process relates to the treatment of oily skin and the composition is applied to oily skin.

According to a particular mode, the composition is applied to the area of the face, in particular the T-zone (forehead, nose, cheeks, chin), in particular the cheeks and the nose.

The invention is illustrated in the following examples.

EXAMPLES 1 to 8 comparative

An aqueous gel according to the invention (Gel 1) and an aqueous gel not forming part of the invention (gels 2 to 8) having the following compositions were prepared:

(Quantities are in percent by weight) Gel 1:

 - 6-phthalimidoperoxyhexanoic acid in aqueous dispersion

at 17% MA (EURECO HC L17® from Solvay) 0.85% MA ie 5% as is

sodium acrylamido 2-methyl propane sulfonate copolymer

90% 2-hydroxyethyl methacrylate in water

(SEPINOV EMT 10 from Seppic) 1, 8% MA or 2% as is

- water qs 100% Gel 2:

 - 6-phthalimidoperoxyhexanoic acid in aqueous dispersion

at 17% MA (EURECO HC L17® from Solvay) 0.85% MA is 5% as such - cetyl hydroxyethyl cellulose 91.3% in a mixture of sodium nitrate, silica, sodium acetate, Polysorbate (POLYSURF 67 from at Aqualon) 0.91% MA is 1% as is - water qs 100%

Gel 3:

- 6-phthalimidoperoxyhexanoic acid in aqueous dispersion

at 17% MA (EURECO HC L17® from Solvay) 0.85% MA ie 5% as is

- hydroxyethyl cellulose (NATROSOL 250 HH R from Aqualon) 1% MA

 - water qs 100% Gel 4:

 - 6-phthalimidoperoxyhexanoic acid in aqueous dispersion

at 17% MA (EURECO HC L17® from Solvay) 0.85% MA ie 5% as is

PEG-136 / Steareth-100l / SMDI Copolymer (Elementis Rheolate FX1 100) 2% MA

- water qs 100%

Gel 5:

 - 6-phthalimidoperoxyhexanoic acid in aqueous dispersion

at 17% MA (EURECO HC L17® from Solvay) 0.85% MA ie 5% as is

Cross-linked acrylate / C ₁ -C ₃ alkyl acrylate polymer (Carbopol ^® Ultrez 20

 Polymer from Noveon) 1% MA - water qs 100%

Gel 6:

- 6-phthalimidoperoxyhexanoic acid in aqueous dispersion

at 17% MA (EURECO HC L17® from Solvay) 0.85% MA ie 5% as is

- Neutralized poly acrylamidomethyl propane sulfonic acid

partially with ammonia and highly crosslinked

 (Hostacerin AMPS® from Clariant) 1% MA - water qs 100%

Gel 7 - 6-phthalimidoperoxyhexanoic acid in aqueous dispersion

 at 17% MA (EURECO HC L17® from Solvay) 0.85% MA ie 5% as is

acrylamide / acrylamido 2-methyl propane sulphonate sodium copolymer in 40% inverse emulsion in isoparaffin / water (Sepigel 305 from Seppic) 2% MA - water qs 100%

Gel 8:

 - 6-phthalimidoperoxyhexanoic acid in aqueous dispersion

 at 17% MA (EURECO HC L17® from Solvay) 0.85% MA, ie 5% as is - sodium / magnesium / lithium silicate (LAPONITE XLG from Rockwood additives)

 0.5% MA

- water qs 100%

The microscopic appearance of each gel was evaluated after different storage times and at different temperatures. The following results were obtained:

Only gel 1 according to the invention has a good stability at 2 months 45 ° C: the gel remains homogeneous without precipitation of 6-phthalimidoperoxyhexanoic acid crystals which remain in dispersion in the gel.

The composition of the gel 1 applied to the oily skin makes it possible to treat it.

Example 9

The following composition was prepared: - 6-phthalimidoperoxyhexanoic acid in aqueous dispersion

at 17% MA (EURECO HC L17® from Solvay) 0.85% MA ie 5% as is

sodium acrylamido 2-methyl propane sulfonate copolymer

90% 2-hydroxyethyl methacrylate in water

(SEPINOVEMTIOdechezSeppic) 1.8% MA ie 2% as is

- isohexadecane 5%

 water qsp100%

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

1. A composition comprising, in a physiologically acceptable aqueous medium, a

 in which : A represents a benzene ring optionally substituted with one or more, preferably up to 4, and even more preferably with 1 or 2 groups chosen from a (C ₁ -C ₅ ) alkyl group, R, identical or different, represents a hydrogen atom, an -OH group, a (C ₁ -C ₅ ) alkyl group, a -COOH group, a -COOR ₁ group, R ₁ representing a (C ₁ -C ₅ ) alkyl group, and  n is an integer ranging from 1 to 5, for example from 1 to 3 or for example from 3 to 5, and their salts; and a copolymer of 2-acrylamido-2-methylpropanesulfonic acid and hydroxylated (C 2 -C 4) alkyl (meth) acrylate, optionally salified. 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 (CrC ₃ ) alkyl group, and n varies from 3 to 5. 3. Composition according to any 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 0.0001% to 30% by weight, relative to the total weight of the composition, preferably ranging from 0.001% to 20% by weight, preferably ranging from 0.01% to 20% by weight, and more preferably ranging from 0.05% to 5% by weight. 5. Composition according to any one of the preceding claims, characterized in that the monomer of C2-C4 alkyl (meth) acrylate hydroxylated is selected from 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2,3-dihydroxypropyl acrylate, 2,3-dihydroxypropyl methacrylate. 6. Composition according to any one of the preceding claims, characterized in that it comprises a copolymer of 2-acrylamido-2-methylpropanesulfonic acid and 2-hydroxyethyl acrylate. 7. Composition according to any one of the preceding claims, characterized in that the copolymer of 2-acrylamido-2-methylpropanesulfonic acid and C2-C4 alkyl (meth) acrylate hydroxyl is present in a content ranging from 0.05% to 20% by weight, relative to the total weight of the composition, preferably ranging from 0.1% to 10% by weight, and preferably ranging from 0.5% to 5% by weight. 8. Composition according to any one of the preceding claims, characterized in that the copolymer of 2-acrylamido-2-methylpropanesulfonic acid and C2-C4 alkyl (meth) acrylate hydroxyl is salified in the form of salt selected alkali metal salts, ammonium salts, amino alcohol salts, amino acid salts. 9. Composition according to any one of the preceding claims, characterized in that the copolymer of 2-acrylamido-2-methylpropanesulfonic acid and C2-C4 alkyl (meth) acrylate hydroxyl is salified in the form of sodium salt. 10. Composition according to any one of the preceding claims, characterized in that it comprises water in a content ranging from 50% to 99% by weight, relative to the total weight of the composition, preferably ranging from 60% to 97% by weight. 1 1. Composition according to any one of the preceding claims, characterized in that it has a pH ranging from 3 to 5. 12. Composition according to any one of the preceding claims, characterized in that it comprises at least one oil selected from linear or branched C 8 -C 15 alkanes, linear or cyclic polydimethylsiloxane silicone oils having from 2 to 7 silicon atoms, polydimethylsiloxanes. 13. Composition according to the preceding claim, characterized in that the oil is present in a content ranging from 0.05% to 50% by weight, relative to the total weight of the composition, preferably ranging from 0.1%. at 30% by weight, and preferably ranging from 1% to 20% by weight. 14. Non-therapeutic cosmetic method for treating the skin, comprising the application to the skin of a composition according to any one of the preceding claims. 15. Non-therapeutic cosmetic process for treating oily skin, comprising the application to oily skin of a composition according to any one of Claims 1 to 13.