COMPOSITION CONTAINING 4-(3-ETHOXY-4-HYDROXYPHENYL)BUTAN-2-ONE, A PRESERVATIVE AND/OR ANTIOXIDANT, A SURFACTANT AND A POLYMER, AND THE METHOD FOR PROCESSING KERATIN MATERIALS FROM THE COMPOSITION

Abstract

The present invention relates to a composition comprising i) at least one 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one compound; ii) at least one preserving agent other than i) and/or antioxidant; iii) at least one surfactant chosen from the surfactants; iv) at least one polymer, notably a thickening polymer, which is preferably organic, and v) optionally a fatty substance. The invention also relates to the use of i) to vi) as antimicrobial agent, to a process for treating keratin materials using the composition comprising i) to vi) and to a kit comprising ingredients i) to vi).

The combination of i) ii), iii), iv) and optionally v) makes it possible to obtain an antimicrobial mixture which has excellent antimicrobial activity, in particular with respect to Aspergillus niger, Escherichia coli, Staphylococcus aureus and Candida albicans. In addition, the formulations remain stable over time while at the same time retaining antimicrobial activity over time even after 7 days, 15 days, 1 month, and at room temperature.

Claims

1. A mixture comprising: i) one or more 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one compounds or one or more organic or mineral base salts thereof, solvates thereof or mixtures thereof; ii) one or more preserving agents other than i) and/or one or more antioxidants; iii) one or more surfactants; iv) one or more thickening polymers; and optionally v) one or more fatty substances; it being understood that when the mixture comprises one or more cationic surfactants, they are in an amount of less than 3% by weight relative to the total weight of i) to v).

2. The mixture as claimed in claim 1, in which the weight ratio i)/ii) ranges from 0.05 to 5.

3. The mixture as claimed in claim 1, in which the preserving agent(s) and/or antioxidants ii) are chosen from organic preserving agents bearing aromatic groups.

4. The mixture as claimed in claim in which ii) is or are chosen from antioxidants.

5. The mixture as claimed in claim 1, in which ii) is or are chosen from 4-hydroxyacetophenone, the salts thereof, and the solvates thereof.

6. A composition comprising the mixture of ingredients i), ii), iii) and iv) and optionally v) as defined in claim 1, it being understood that said composition comprises an amount of cationic surfactants of less than 0.5% by weight.

7. The composition as claimed in claim 6, which comprises one or more surfactants chosen from nonionic and anionic surfactants, and a mixture thereof.

8. The composition as claimed in claim 6, which comprises one or more nonionic surfactants chosen from: (poly)ethoxylated fatty alcohols; glycerolated fatty alcohols; alkylpolyglycosides or a mixture thereof.

9. The composition as claimed in claim 6, which comprises one or more anionic surfactants chosen from: alkyl carboxylic acids, alkyl sulfates, alkyl ether sulfates, alkylamido ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates, alkylsulfonates, alkylamidesulfonates, alkylarylsulfonates, α-olefin sulfonates, paraffin sulfonates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, alkylamide sulfosuccinates, alkyl sulfoacetates, acyl sarcosinates, acyl glutamates, alkyl sulfosuccinamates, acyl isethionates and N-acyltaurates, salts of alkyl monoesters of polyglycoside-polycarboxylic acids, salts of alkyl diesters of polyglycoside-polycarboxylic acids, acyl lactylates, D-galactoside-uronic acid salts, alkyl ether carboxylic acid salts, alkylaryl ether carboxylic acid salts, alkylamido ether carboxylic acid salts, and the corresponding non-salified forms of all these compounds, the alkyl and acyl groups of all these compounds including from 8 to 30 carbon atoms and the aryl group denoting a phenyl group which may be oxyethylenated.

10. The composition as claimed in claim 6, in which the amount of surfactants ranges from 0.5% to 30% by weight relative to the total weight of the composition of the invention.

11. The composition as claimed in claim 6, which comprises one or more fatty substances preferably chosen from: a) butters; b) waxes; c) non-liquid fatty alcohols; d) non-liquid fatty acid and/or fatty alcohol esters; e) esters of monoalcohols, at least one from among the alcohol or of the acid from which said esters are derived is branched; f) cyclic polydialkylsiloxanes including from 3 to 7.

12. The composition as claimed in claim 6, which comprises one or more fatty substances in an amount ranging from 1% to 40% by weight relative to the total weight of the composition.

13. The composition as claimed in claim 6, which comprises one or more thickening organic polymers of natural or synthetic origin, which are associative or non-associative.

14. The composition as claimed in claim 6, which comprises one or more thickening organic polymers resulting from the (co)polymerization:
of acrylate monomer CH.sub.2═C(R′)—COOR′″  (VIa) and/or
of acrylamide monomer CH.sub.2═C(R′)—CO—N(R″)-LY.sup.−M  (VIb) in which formulae (VIa) and (VIb): R′ and R″, which may be identical or different, represent a hydrogen atom or a (C.sub.1-C.sub.6)alkyl group, R′″ represents an alkali metal, an alkaline-earth metal, a hydrogen atom or a (C.sub.1-C.sub.6)alkyl group optionally substituted with one or more hydroxyl, carboxyl or amino groups; L representing a linear or branched, saturated or unsaturated, cyclic or acyclic, divalent hydrocarbon-based group optionally interrupted and/or substituted with one or more heteroatoms and comprising from 1 to 20 carbon atoms; Y.sup.− represents an anionic group.

15. The composition as claimed in claim 6, which comprises one or more thickening organic polymers bearing sugar units.

16. The composition as claimed in claim 6, which comprises one or more thickening organic polymers in a content ranging from 0.01% to 10% by weight relative to the total weight of the composition.

17. The composition as claimed in claim 6, which comprises one or more fatty substances chosen from a) butters; b) waxes; c) non-liquid fatty alcohols; d) non-liquid fatty acid and/or fatty alcohol esters e) esters of monoalcohols, at least one from among the alcohol or of the acid from which said esters are derived is branched; f) cyclic polydialkylsiloxanes including from 3 to 7, and one or more surfactants chosen from 4-hydroxyacetophenone, the salts thereof, and the solvates thereof, the fatty substance/surfactant(s) weight ratio of which is inclusively between 5 and 20.

18. The composition as claimed in claim 6, which comprises one or more fatty substances chosen from a) butters; b) waxes; c) non-liquid fatty alcohols; d) non-liquid fatty acid and/or fatty alcohol esters; e) esters of monoalcohols, at least one from among the alcohol or of the acid from which said esters are derived is branched; f) cyclic polydialkylsiloxanes including from 3 to 7 and one or more surfactants chosen from nonionic and anionic surfactants, and a mixture thereof, and one or more thickening organic polymers of natural or synthetic origin, which are associative or non-associative, the weight ratio of the fatty substance/sum of surfactant(s) and polymer(s) [surfactant(s)+polymer] of which is inclusively between 0.8 and 10.

19. The composition as claimed in claim 6, which comprises an aqueous phase and an organic or oily phase.

20. The composition as claimed in claim 6, which comprises one or more organic solvents.

21. The composition as claimed in claim 6, which comprises one or more organic solvents present in amounts inclusively between 0.1% and 40% by weight relative to the total weight of the composition.

22. A non-therapeutic cosmetic treatment process comprising the application to said keratin materials of a composition as claimed in claim 6.

23. A process for preserving a composition comprising a physiologically acceptable medium incorporating into said composition an antimicrobial mixture as defined in claim 1 or a composition thereof.

Description

EXAMPLES

Example 1: Determination of the Synergistic Antimicrobial Activity as MIC

[0531] The demonstration of a synergistic antimicrobial activity effect with a mixture of 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one (referred to as substance A) and of an alcohol compound (referred to as substance B) was performed by calculating the synergy index (or FIC index) according to the following formula:

FIC Index=(CMI avec B/CMI de A)+(CMI de B avec A/CMI de B)  [Math. 1]

with: [0532] MIC of A with B: minimum concentration of product A in the combination A+B which makes it possible to obtain an inhibitory effect; [0533] MIC of B with A: minimum concentration of product B in the combination A+B which makes it possible to obtain an inhibitory effect; [0534] MIC of A: minimum inhibitory concentration of product A alone; [0535] MIC of B: minimum inhibitory concentration of product B alone.
This formula was described for the first time in the article by F. C. Kull, P. C. Eisman, H. D. Sylwestrowka, and R. L. Mayer, Applied Microbiology 9:538-541, 1961.

[0536] For each compound tested alone, the MIC is considered as the first concentration which makes it possible to obtain a microbial growth percentage of less than or equal to 25%.

[0537] As regards the combinations tested, MIC of A with B and MIC of B with A are the respective concentrations of A and of B in the combinations which make it possible to obtain a microbial growth percentage of less than or equal to 25%.

[0538] Interpretation of the FIC Index:

[0539] When the FIC index value is less than or equal to 1, it is considered that the combination of test compounds has a synergistic effect.

[0540] The summary of the results obtained is presented in the following tables.

[0541] The combination of compounds A and B, and the compositions containing them, were tested on the following strains or a part thereof: Aspergillus niger, Escherichia coli, Staphylococcus aureus, and Candida albicans.

[0542] The microbial strain Aspergillus niger ATCC 6275, and a double-concentration Sabouraud broth liquid culture medium supplemented with polyoxyethylenated (20 OE) sorbitan monopalmitate (Tween 40 from Croda) and Phytagel© BioReagent were used (i.e. a mixture of 5 g of Phytagel+0.6 g Tween 40+60 g of Sabouraud broth).

[0543] The microbial strain Staphylococcus aureus ATCC 6538 and a double-concentration nutrient broth liquid culture medium were used.

[0544] The microbial strain Candida albicans ATCC 10231, and a double-concentration Sabouraud broth liquid culture medium were used (i.e. a mixture of 5 g of Phytagel+0.6 g Tween 40+60 g of Sabouraud broth).

[0545] A 96-well microplate at an incubation temperature of 32.5° C. is used.

[0546] The incubation time of the microplate is: [0547] from 24 to 30 h under aerobic conditions for microbial Aspergillus niger ATCC 6275; [0548] from 18 to 24 h under aerobic conditions for Candida albicans ATCC 10231, Pseudomonas aeruginosa ATCC 9027 and Staphylococcus aureus ATCC 6538;

[0549] Tests

[0550] For each compound:

[0551] A=compound i) 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one

[0552] B=compound ii) preserving agent and/or antioxidant:

[0553] B1: 4-hydroxyacetophenone, B2: salicylic acid

[0554] Tests of Compounds A and B Alone

[0555] 50 μl of each of the daughter solutions obtained containing compound A or B are added to the microplate wells. 100 μl of Sabouraud liquid nutrient broth inoculated at double concentration with the Aspergillus niger strain and 50 μl of solution are also added thereto.

[0556] Tests of Compounds A and B as a Mixture

[0557] 50 μl of each of the daughter solutions obtained containing compound A and 50 μl of each of the daughter solutions obtained containing compound B are added to the microplate wells. 100 μl of Sabouraud liquid nutrient broth inoculated at double concentration with the strain Aspergillus niger are also added thereto.

[0558] Microbial Growth Control

[0559] A positive microbial growth control was also prepared. The positive microbial growth control corresponds to the mixture of 100 μl of aqueous 1‰ agar solution with 100 μl of Sabouraud liquid nutrient broth inoculated at double concentration with the strain Aspergillus niger in the absence of compounds A and B.

[0560] Absorbance Control for Compounds A and B Alone

[0561] An absorbance control was performed in parallel on compounds A and B alone. This control corresponds to 100 μl of double concentration sterile Sabouraud liquid nutrient broth+100 μl of double concentration compound A or B.

[0562] In the three cases (absorbance control, growth control and test), the final volume present in each of the microplate wells is 200 μl.

[0563] In the two cases (test and control), the inoculum represents the concentration of the Aspergillus niger strain present in the final volume of the wells (200 μl) and is between 2 and 6×10.sup.5 cfu/ml of Aspergillus niger.

[0564] The minimum inhibitory concentration (MIC) of each compound A and B alone and in combination was determined in a known manner by means of optical density measurements at a wavelength of 620 nm.

[0565] The test as described above (tests, absorbance control and growth control) was performed again to test the combination A+B on the following strains: Aspergillus niger, Escherichia coli, Staphylococcus aureus, and Candida albicans

[0566] The following results were obtained with compound B1=4-hydroxyacetophenone:

[0567] The antimicrobial properties were also evaluated with other compositions, such as those detailed below in table 3 in which the ingredients are given by weight (g) per 100 g of composition. The properties were evaluated at 7 days, 14 days and 1 month.

TABLE-US-00001 TABLE 1 Com- Com- Com- position parative parative 1 composi- composition Ingredients Invention tion 2 3 A ingredient, i) 0.7 0.7 — B1, ingredient ii) 0.2 — 0.2 Propylene glycol stearate (20 0.8 0.8 0.8 EO), ingredient iii) Glyceryl 2 2 2 monostearate/distearate/ polyethylene glycol stearate (100 EO) mixture, ingredient iii) Fatty acid (mainly stearic acid) 3 3 3 of plant origin, ingredient iii) Acrylamide/sodium acrylamido- 2.2 2.2 2.2 2-methylpropanesulfonate copolymer Polysorbate 80/I- C16, ingredient iv) Cetyl alcohol, ingredient v) 0.5 0.5 0.5 Stearyl alcohol, ingredient v) 0.5 0.5 0.5 Myristyl myristate, ingredient v) 2 2 2 White beeswax, ingredient v) 1 1 1 Shea butter, ingredient v) 2 2 2 Mixture of caprylic and capric 3.1 3.1 3.1 acid triglycerides, ingredient v) Isopropyl isostearate, ingredient 1.2 1.2 1.2 v) Cyclohexadimethylsiloxane, 6 6 6 ingredient v) Glycerol 7.0 7.0 7.0 Mineral pigment 0.15 0.15 0.15 Organic pigment 0.01 0.01 0.01 Triethanolamine (basic pH 0.15 0.15 0.15 agent) Vitamin E: DL-α-tocopherol 0.5 0.5 0.5 Water qs 100 qs 100 qs 100

[0568] The results on the microbial strain Escherichia coli at 7 days are given in the table below:

TABLE-US-00002 TABLE 2 Compositions Number of microbes after 7 days Composition 1 (invention) <200 Composition 2 (comparative) 2.4 × 10.sup.4 Composition 3 (comparative) 2.1 × 10.sup.5

[0569] The results on the microbial strain Staphylococcus aureus at 7 and 14 days are given in the table below:

TABLE-US-00003 TABLE 3 Number of microbes Number of microbes Compositions after 7 days after 14 days Composition 1 (invention) 3.7 × 10.sup.5 3.4 × 10.sup.3 Composition 2 2.4 × 10.sup.6 9.6 × 10.sup.5 (comparative) Composition 3 1.9 × 10.sup.6 3.0 × 10.sup.4 (comparative)

[0570] The results on other microbial strains at 7 days, 14 days and then 1 month are given in the table below:

TABLE-US-00004 TABLE 4 After Compositions/Strains targeted After 7 days After 14 days 1 month Composition 1 (invention) Candida albicans 8.6 × 10.sup.3 <200 <200 Aspergillus niger 6.8 × 10.sup.5 2.0 × 10.sup.3 <200 Composition 2 (comparative) Candida albicans 2.0 × 10.sup.5 8.2 × 10.sup.4 3.0 × 10.sup.3 Aspergillus niger 4.1 × 10.sup.6 5.0 × 10.sup.6 5.4 × 10.sup.6 Composition 3 (comparative) Candida albicans 3.4 × 10.sup.5   1 × 10.sup.5 3.8 × 10.sup.4 Aspergillus niger 3.4 × 10.sup.6 3.4 × 10.sup.6 2.3 × 10.sup.6
It is seen from the results in the tables above that the combination of A and 1B1 according to the invention allows a marked antimicrobial improvement, this being after 7 days, 15 days or even one month for a wide variety of microbial strains (Aspergillus niger, Escherichia coli, Staphylococcus aureus, and Candida albicans).

[0571] The following compositions with ii) compound 1B2=salicylic acid were prepared:

TABLE-US-00005 TABLE 5 Com- Com- position parative 4 composition Ingredients Invention 5 A, ingredient i) 0.7 0.7 B2, ingredient ii) 0.2 0.2 Propylene glycol stearate (20 EO), 0.8 0.8 ingredient iii) Glyceryl monostearate/distearate/ 2 2 polyethylene glycol stearate (100 EO) mixture, ingredient iii) Stearic acid, ingredient iii) 3 — Dipalmitoylethylhydroxyammonium — 3 methosulfate (30% by weight) and cetearyl alcohol Acrylamide/sodium acrylamido-2- 2.2 2.2 methylpropanesulfonate copolymer Polysorbate 80/I-C16, ingredient iv) Cetyl alcohol, ingredient v) 0.5 0.5 Stearyl alcohol, ingredient v) 0.5 0.5 Myristyl myristate, ingredient v) 2 2 White beeswax, ingredient v) 1 1 Shea butter, ingredient v) 2 2 Mixture of caprylic and capric acid 3.1 3.1 triglycerides, ingredient v) Isopropyl isostearate, ingredient v) 1.2 1.2 Cyclohexadimethylsiloxane, ingredient v) 6 6 Glycerol 7.0 7.0 Mineral pigment (mica) 0.15 0.15 Organic pigment 0.01 0.01 Triethanolamine (pH 6.4 agent) 0.35 0.28 Vitamin E: DL-α-tocopherol 0.5 0.5 Water qs 100 qs 100

[0572] It is seen that comparative composition 5 comprising a cationic surfactant is much less stable than composition 4 according to the invention. In addition, the viscosity of composition 4 according to the invention is 32.5 poises, whereas comparative composition 5 is much more viscous, since its viscosity is 51.5 poises. These viscosity values were measured at 25° C. and at atmospheric pressure.

[0573] Other Comparative Tests:

[0574] The following two compositions were prepared; the amounts of the ingredients are given in g per 100 g of composition:

TABLE-US-00006 TABLE 6 Com- Com- parative position composi- 7 Ingredients tion 6 invention Sorbitan tristearate (Span 65 V from Croda) 0.9% 0.9% (ingredient iii) Mixtureofglycerylmonostearate/distearate   3%   3% (36/64)/potassium stearate (Tegin Pellets from Goldschmidt) (ingredient iii) Polyethylene glycol stearate (40 ethylene oxide   2%   2% units - 40 EO) (ingredient iii) 4-(3-Ethoxy-4-hydroxyphenyl)butan-2-one - 0.05% 0.05% EZ (ingredient D Phenoxyethanol (ingredient ii) 0.2% 0.2% Caffeine (ingredient ii) 0.1% 0.1% 1,3-Propanediol   3%   3% Mixture of liquid petroleum jelly (mineral oil),   4%   4% microcrystalline wax and paraffin (Vaseline Blanche Codex 236 from Aiglon) (ingredient v) Stabilized shea olein (Shea Olein from Olvea)   1%   1% (ingredient v) Cyclopentadimethylsiloxane (ingredient v)   5%   5% Cetyl alcohol (ingredient v)   4%   4% Apricot kernel oil (ingredient v) 0.3% 0.3% Hydrogenated polyisobutene (Parleam from   2% NOF Corporation) Acrylamide/sodium acrylamido-2- —   2% methylpropanesulfonatecopolymer Polysorbate 80/I-C16 (ingredient iv) Myristyl myristate (ingredient v)   2%   2% Stearic acid (ingredient iii) 1.2% 1.2% Citric acid 0.2% 0.2% Glycerol   3%   3% Sodium hydroxide 0.05%  0.05%  Water qs 100 qs 100

[0575] The composition according to the invention is glossy, aerated, white, with a “base” odor.

[0576] Microscopic Evaluation of the Compositions:

[0577] It is seen under a microscope in white light, with a magnification of ×400 (Leica DM2500 with Archimed Microvision software) that comparative composition 6 comprises vacuoles, whereas composition 7 according to the invention is more structured, with no visible vacuoles, making it more stable.

[0578] Sensory Evaluation:

[0579] The application of composition 7 of the invention is fresher, easier, more viscous and applies better, with a pleasant sensation by rotation of the fingers on the skin for significantly longer than that obtained with composition 6.

[0580] It is also seen after application of composition 7 according to the invention to the skin, and a much more matt and soft-focus appearance than that obtained with comparative composition 6.

[0581] Measurement of the Soft Focus/Matt Effect on Keratin Materials: To measure the transmittance, the haze and the brightness, use was made of a Byk hazemeter, model: HazeGard Plus.

[0582] The matt effect/soft focus results after application to the skin, judged by a panel of evaluators, are corroborated with the transmittance, haze, brightness and gloss measurements. To quantify the transmitted light of a formulation and also its soft focus capacity, the “haze” parameters are measured. The haze measurement consists in determining the amount of light rays deviated from their trajectory by the sample. It makes it possible to quantify the soft-focus power of the material.

[0583] Study conditions: Room temperature: 25° C., film drying temperature: 25° C., film drying time: 1 h.

[0584] Elcometer spreader, model: 4340—A transparent 100 micron sheet is placed on the spreader, adjusted to a thickness in position of 25 microns, the sample is then added and the film is then left to dry for 1 hour at room temperature. The transparent sheet onto which the sample 25 microns thick is spread is then placed on the lenses of the apparatus and the H (haze) and B (brightness) values are measured.

[0585] To measure the gloss, use is made of a Byk glossmeter, model: Micro TRI gloss. The spreading is identical to that described above, with a measurement being taken directly using a transparent sheet placed on a black surface and the glossmeter.

TABLE-US-00007 TABLE 7 Comparative Composition 7 Observations/measurements composition 6 Invention Haze 22.77 53.28 Brightness 48.15 12.15 Sheen 40.32 18.65

[0586] It is seen from the results of table 7 that the composition according to the invention, composition 7, makes it possible to significantly improve the soft-focus and matt effect relative to the comparative composition.