WO2012076345A1

WO2012076345A1 - Cosmetic composition comprising an imidoperoxycarboxylic acid, an imidocarboxylic acid and copolymer of 2-acrylamido-2-methylpropanesulphonic acid

Info

Publication number: WO2012076345A1
Application number: PCT/EP2011/071050
Authority: WO
Inventors: Véronique Chevalier; Benoit Muller
Original assignee: L'oreal
Priority date: 2010-12-06
Filing date: 2011-11-25
Publication date: 2012-06-14

Abstract

T he invention relates to a composition comprising, in a vehicle medium, a) an imidoperoxycarboxylic acid compound of formula (I): 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 group -COOR₁, where represents a (C₁-C₅)alkyl group, and - n is an integer from 1 to 12, and salts thereof; b) an imidocarboxylic acid of formula (II): in which: - 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 (C₁-C₅)alkyl group, - m is an integer from 1 to 12, and salts thereof; c ) a copolymer of 2-acrylamido-2-methylpropanesulphonic acid and C₂-C₄ hydroxyalkyl (meth)acrylate, the compounds (I) and (II) being present in a compound (l)/compound (II) weight ratio of from 4 to 20.

Description

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.

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

6-Phthalimidoperoxyhexanoic acid, though, 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.

The Applicant has now demonstrated that 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 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.

In one preferred embodiment, 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:

in which:

- 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-C₅)alkyl group,

- R, identical or different at each occurrence, represents a hydrogen atom, an -OH group, a (CrC₅)alkyl group, a -COOH group, or a group -COOR₁, where represents a (C C₅)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,

and salts thereof.

The imidoperoxycarboxylic acid derivative used in the composition according to the invention is selected from the compounds of formula (II) below:

in which:

- 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-C₅)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 NH₄ ⁺; 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 (CrC₅)alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and pentyl.

In one embodiment a percarboxylic imidoaromatic 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 (CrC₃)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.

The compounds of formula (I) include phthali idoperoxyacetic acid (A = benzene; R = H; n = 1), 2-phthalimidoperoxypropionic a d, 3-phthalimidoperoxypropionic 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 and 2- phthalimidomonoperoxysuccinic acid.

The compound of formula (I) is preferably 6-phthalimidoperoxyhexanoic acid, also called phthalimidoperoxycaproic acid or 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. Its I NCI name is phthalimidoperoxycaproic acid.

6-Phthalimidoperoxyhexanoic acid (abbreviated PAP) is available in particular in two commercial forms from Solvay.

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.

In one embodiment, 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:

and also 8-phthalimidooctanoic acid, 9-phthalimidononanoic

phthalimidodecanoic acid and 12-phthalimidododecanoic acid.

The compound of formula (II) is preferably 6-phthalimidohexanoic acid, also called phthalimidocaproic acid, or ε-phthalimidohexanoic acid (CAS No.: 4443-26-9). Its chemical structure is as follows:

It corresponds to a compound of formula (II) in which A' represents an unsubstituted benzene ring and m = 5.

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.

The above-described compounds (I) and (II) are present in the composition according to the invention in a compound (l)/compound (II) weight ratio of from 4 to 20.

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.

When the 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).

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

In one preferred embodiment, 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.

The 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. In one embodiment of the invention, 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 triglycerides (such as those sold under the name Miglyol 812 N by Sasol or Myritol 318 by Cognis).

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.

The 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:

ascorbic acid, kojic acid, caffeic acid, salicylic acid and derivatives thereof, 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-hydroxynonanoic acid, 2-hydroxydecanoic acid, 2- hydroxyundecanoic acid, 2-hydroxydodecanoic acid, 2-hydroxytetradecanoic acid, 2- hydroxyhexadecanoic acid, 2-hydroxyoctadecanoic acid, 2-hydroxytetracosanoic acid, 2- hydroxyeicosanoic acid, mandelic acid, benzoic acid, phenyllactic acid, gluconic acid, galacturonic acid, aleuritic acid, ribonic acid, tartronic acid, tartric acid, malic acid, fumaric acid, retinoic acid and derivatives thereof, benzene 1 ,4-di(3-methylidene-10- camphorsulphonic 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 xanthic derivatives, β- glycyrrhetinic acid, asiatic acid and mixtures thereof.

The 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).

The 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.

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.

In one particular embodiment, the composition is applied to the facial zone, more particularly the T zone (forehead, nose, cheeks, chin), more particularly the cheeks and the nose. The invention is illustrated in the examples which follow:

EXAMPLES 1 to 6 (comparative) 3 inventive aqueous gels (gels 2 to 4) and 3 non-inventive aqueous gels (gels 1 , 5 and 6) were prepared, having the following compositions:

(the amounts are expressed as weight percentages ; a.i. = active ingredient) Gel:

- 6-Phthalimidoperoxyhexanoic acid in aqueous dispersion containing 17% a.i.

(Eureco HC L17® from Solvay) 1.70% a.i. or 10% as is

- 6-Phthalimidohexanoic acid X% a.i.

- Sodium 2-acrylamidomethylpropanesulphonate/

2-hydroxyethyl methacrylate copolymer, 90% in water

(Sepinov EMT 10 from SEPPIC) 1.8% a.i. or 2% as is

- Sodium hydroxide 0.008%

- Water qs 100%

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.

The results obtained were as follows:

% of 6-phthalimido- Ratio (1) % acid A

hexanoic acid remaining

after 2

months at

45°C

Gel 1 (N.I.) 0 - 66

Gel 2 0.1 17 76 Gel 3 0.2 8.5 85

Gel 4 0.4 4.25 75

Gel 5 (N.I.) 0.85 2 72

Gel 6 (N.I.) 1.7 1 69

N.I.: not inventive

(1) 6-Phthalimidoperoxyhexanoic acid/6-phthalimidohexanoic acid weight ratio Gels 2 to 4 according to the invention exhibit good stability at 2 months at 45°C: the amount of 6-phthalimidoperoxyhexanoic acid is greater than that of the other gels, gels 1 , 5 and 6, which do not form part of the invention.

The composition of gels 2 to 4 may be applied for facial skincare, and more particularly for treating greasy skin.

Example 7:

The following composition was prepared:

- 6-Phthalimidoperoxyhexanoic acid in aqueous dispersion containing 17% a.i.

(Eureco HC L17® from Solvay) 1.70% a.i. or 10% as is

- 6-Phthalimidohexanoic acid 2 % a.i.

- Sodium 2-acrylamidomethylpropanesulphonate/

2-hydroxyethyl methacrylate copolymer, 90% in water

(Sepinov EMT 10 from SEPPIC) 1.8% a.i. or 2% as is

- Capric/caprylic acid triglycerides

(Miglyol 812 N from SASOL) 5%

- Water qs 100%

The 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.

Claims

1. Composition comprising, in an aqueous vehicle medium:

in which:

and salts thereof; b) an imidocarboxylic acid of formula (II) below:

in which:

- 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 (CrC₅)alkyl group,

- m is an integer from 1 to 12,

and salts thereof; c ) a copolymer of 2-acrylamido-2-methylpropanesulphonic acid and C2-C4 hydroxyalkyl (meth)acrylate, the compounds (I) and (II) being present in a compound (l)/compound (II) weight ratio of from 4 to 20.

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 1 to 5.

3. Composition according to either of the preceding claims, characterized in that the compound of formula (I) is 6-phthalimidoperoxyhexanoic acid.

4. Composition according to any of the preceding claims, characterized in that the compound of formula (I) is present in an amount of from 0.0001 % to 30% by weight, relative to the total weight of the composition, preferably of from 0.001 % to 20% by weight, more preferably of from 0.01 % to 20% by weight, and more preferably still of from 0.05% to 5% by weight.

5. Composition according to any of the preceding claims, characterized in that the compound of formula (II) is 6-phthalimidohexanoic acid.

6. Composition according to any of the preceding claims, characterized in that the compound of formula (II) is present in an amount of from 0.001 % to 3% by weight, relative to the total weight of the composition, preferably of from 0.005% to 2% by weight, more preferably of from 0.01 % to 1 % by weight, and more preferably still of from 0.05% to 0.5% by weight.

7. Composition according to any of the preceding claims, characterized in that the compound (l)/compound (II) weight ratio is from 5 to 14, preferably from 6 to 13, and more preferably from 6.5 to 10.5.

8. Composition according to any of Claims 1 to 7, characterized in that it comprises a 2- acrylamido-2-methylpropanesulphonic acid-2-hydroxyethyl acrylate copolymer.

9. Composition according to any of Claims 1 to 8, characterized in that it has a pH of from 3 to 5.

10. Composition according to any of the preceding claims, characterized in that it comprises 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, and polydimethylsiloxanes.

1 1. Composition according to the preceding claim, characterized in that the oil is present in an amount of from 0.05% to 50% by weight, relative to the total weight of the composition, preferably of from 0.1 % to 30% by weight, and more preferably of from 1 % to 20% by weight.

12. Cosmetic, non-therapeutic, method for treating the skin, which comprises applying to the skin a composition comprising, in a vehicle medium:

a) an imidoperoxycarboxylic acid of formula (I) below:

in which:

- R, identical or different at each occurrence, represents a hydrogen atom, an -OH group, a (CrC₅)alkyl group, a -COOH group, or a group -COOR₁, where represents a

(CrC₅)alkyl group, and

and salts thereof; b) an imidocarboxylic acid of formula (II) below:

in which: - 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-C₅)alkyl group,

- m is an integer from 1 to 12,

and salts thereof; the compounds (I) and (II) being present in a compound (l)/compound (II) weight ratio of from 4 to 20, preferably from 5 to 14, more particularly from 6 to 13, and more preferably from 6.5 to 10.5.

13. Method 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 1 to 5.

14. Method according to any of Claims 12 to 13, characterized in that the compound of formula (I) is 6-phthalimidoperoxyhexanoic acid.

15. Method according to any of Claims 12 to 14, characterized in that the compound of formula (I) is present in an amount of from 0.0001 % to 30% by weight, relative to the total weight of the composition, preferably of from 0.001 % to 20% by weight, more preferably of from 0.01 % to 20% by weight, and more preferably still of from 0.05% to 5% by weight.

16. Method according to any of Claims 12 to 15, characterized in that the compound of formula (II) is 6-phthalimidohexanoic acid.

17. Method according to any of Claims 12 to 16, characterized in that the compound of formula (II) is present in an amount of from 0.001 % to 3% by weight, relative to the total weight of the composition, preferably of from 0.005% to 2% by weight, more preferably of from 0.01 % to 1 % by weight, and more preferably still of from 0.05% to 0.5% by weight.

18. Method according to any of Claims 12 to 17, characterized in that the composition comprises an aqueous medium.

19. Method according to any of Claims 12 to 18, characterized in that the composition comprises a copolymer of 2-acrylamido-2-methylpropanesulphonic acid and C2-C4 hydroxyalkyl (meth)acrylate.

20. Method according to any of Claims 12 to 19, characterized in that the composition comprises a 2-acrylamido-2-methylpropanesulphonic acid-2-hydroxyethyl acrylate copolymer.

21. Method according to any of Claims 12 to 20, characterized in that the composition has a pH of from 3 to 5.

22. Cosmetic, non-therapeutic, method for treating greasy skin, which comprises applying to the greasy skin a composition according to any of Claims 1 to 1 1.