FR3068209B1 - ANTIMICROBIAL MIXTURE CONTAINING 4- (3-ETHOXY-4-HYDROXYPHENYL) BUTAN-2-ONE AND 1,3-PROPANEDIOL, AND COSMETIC COMPOSITION CONTAINING SAME - Google Patents

Abstract

The invention relates to an antimicrobial mixture containing 4- (3-ethoxy-4-hydroxyphenyl) butan-2-one and 1,3-propanediol, and a cosmetic composition containing such a mixture. Application to the care, makeup and cleansing of keratin materials.

Description

The subject of the present invention is an antibacterial mixture containing 4- (3-ethoxy-4-hydroxyphenyl) butan-2-one and 1,3-propanediol, as well as a cosmetic composition containing such a mixture.

4- (3-Ethoxy-4-hydroxyphenyl) butan-2-one (ketone compound) is a substance of interest as a preservative of cosmetic compositions for protecting the compositions from microbial contamination, as described in WO 2011/039445 .

However, it is desirable to incorporate said ketone compound in reduced concentration in compositions, especially cosmetic or dermatological, while maintaining a good antimicrobial preservation performance. It is therefore sought for this purpose combinations of the ketone compound with other compounds having antimicrobial efficacy.

The inventors have discovered, unexpectedly, that the combination of 4- (3-ethoxy-4-hydroxyphenyl) butan-2-one with 1,3-propanediol in particular podaler ratios makes it possible to obtain an antimicrobial mixture having a synergy of antimicrobial activity, in particular on molds, in particular on Aspergillus niger. The results of Example 1 described hereinafter show the synergistic antimicrobial activity obtained with the minimum inhibitory concentration (MIC) measurements made with several mixtures. The antimicrobial activity is considered to be synergistic when the antimicrobial mixture makes it possible to obtain a percentage of growth of the strain of less than or equal to 20%.

Application FR-A-2973227describes a cosmetic composition containing 4- (3-ethoxy-4-hydroxyphenyl) butan-2-one and a particular hydrophilic solvent including 1,3-propanediol. The latter makes it possible to solubilize the ketone compound. This document does not describe an antimicrobial property for the mixture described.

More specifically, the subject of the invention is an antimicrobial blend comprising or consisting of (or consisting of) 4- (3-ethoxy-4-hydroxyphenyl) butan-2-one and 1,3-propanediol present in the present invention. in amounts such that the weight ratio of 4- (3-ethoxy-4-hydroxyphenyl) butan-2-one / 1,3-propanediol ranges from 0.02 to 0.15. The subject of the invention is also a composition, in particular a cosmetic or dermatological composition, comprising in a physiologically acceptable medium the said mixture described above. The subject of the invention is also a non-therapeutic cosmetic treatment process for keratinous materials comprising the application to the keratin materials of a composition as described above. The process may be a cosmetic process for caring for or making up or cleaning keratin materials.

4- (3-Ethoxy-4-hydroxyphenyl) butan-2-one is a compound of formula

Advantageously, 4- (3-ethoxy-4-hydroxyphenyl) butan-2-one and 1,3-propanediol are present in said mixture in a content such that the weight ratio 4- (3-ethoxy-4-hydroxyphenyl) Butan-2-one / 1,3-propanediol ranges from 0.02 to 0.07.

The compound 4- (3-ethoxy-4-hydroxyphenyl) butan-2-one may be present in the composition according to the invention, in a content ranging from 0.01% to 5% by weight, relative to the total weight of the composition, preferably ranging from 0.01% to 3% by weight, preferably ranging from 0.01 to 2.5% by weight, and more preferably ranging from 0.01 to 2% by weight. The invention also relates to a composition comprising, in a physiologically acceptable medium, the antimicrobial mixture described above.

Physiologically acceptable medium means a medium compatible with keratin materials of human beings such as the skin, the scalp, the hair, the nails. The said medium may comprise one or more additional ingredients, distinct from the ketone compound and 1,3-propanediol.

The composition may comprise at least one additional ingredient selected from water, oils, polyols having 2 to 10 carbon atoms, gelling agents, surfactants, film-forming polymers, dyestuffs, fragrances, fillers, UV filters, plant extracts, cosmetic and dermatological active ingredients, and salts.

The composition according to the invention may comprise an aqueous phase.

The composition may comprise water which may be present in a content ranging from 5% to 90% by weight, based on the total weight of the composition, and preferably ranging from 35% to 75% by weight.

The composition may also comprise a water-miscible polyol at ambient temperature (25 ° C.), chosen in particular from polyols having in particular from 2 to 10 carbon atoms, preferably having from 2 to 6 carbon atoms, such as glycerine, the

pylene glycol, 1,3-propanediol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol, diglycerine.

The compositions according to the invention may be in the form of oil-in-water (O / W) or water-in-oil (W / O) or multiple (triple: W / O / E or H / E / H), oily solutions, oily gels, aqueous solutions, aqueous gels, solid compositions. These compositions are prepared according to the usual methods.

The compositions according to the invention can be more or less fluid and have the appearance of a white or colored cream, an ointment, a milk, a lotion, a serum, a paste, of a foam. They may optionally be applied to the skin in the form of an aerosol. They may also be in solid form, for example in the form of a stick or a compact powder.

The composition according to the invention may especially be in the form of: a makeup product, in particular the skin of the face, of the body or of the lips or eyelashes; - an aftershave gel or lotion; shaving product; - a deodorant (stick, roll-on, aerosol) - a depilatory cream; in the form of a personal hygiene composition such as a shower gel or a shampoo; a pharmaceutical composition; a solid composition such as a soap or a cleaning roll; an aerosol composition also comprising a propellant under pressure; - a styling lotion, a styling cream or gel, a dyeing composition, a permanent composition, a lotion or a fall-prevention gel, an after-treatment shampoo; - a care composition or cleansing of the skin. The subject of the invention is also a process for preparing a composition, in particular a cosmetic or dermatological composition, comprising a step of mixing 4- (3-ethoxy-4-hydroxyphenyl) butan-2-one and 1,3-propanediol. and one or more additional ingredients, especially cosmetic or dermatological, such as those described above. The invention is further illustrated in the following example. The contents of the ingredients are expressed in percentage by weight.

EXAMPLE 1 Determination of the Synergistic Antimicrobial Activity in MIC on the Microbial Strain Aspergillus niger

Demonstration of a synergistic effect of antimicrobial activity with a mixture of 4- (3-ethoxy-4-hydroxyphenyl) butan-2-one (referred to as Substance A) and 1,3-propanediol (referred to as Substance B) is realized by calculating the synergy index (or FIC index) according to the following formula:

with: CMIa with B: minimum concentration of product A in the association A + B making it possible to obtain a CMIb inhibiting effect with A: minimum concentration of product B in the association A + B making it possible to obtain the inhibitory effect. CMIa: minimal inhibitory concentration of product A alone. MICb: minimal inhibitory concentration of product B alone.

This formula has been 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.

For each compound tested alone, the MIC is considered the first concentration to obtain a percentage of microbial growth of less than or equal to 20%.

Regarding the associations tested, CMIa with b and CMIb with a are the respective concentrations of A and B in the combinations allowing to obtain a percentage of microbial growth less than or equal to 20%.

Interpretation of the FIC Index:

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

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

The microbial strain Aspergillus niger ATCC 6275 was used, and Sabouraud broth liquid culture medium supplemented with polyoxyethylenesorbitan monopalmitate (20 EO) (Tween 40 from Croda) and Phytagel © BioReagent, at double concentration (either a mixture). of 5 g Phytagel +0.6 g tween 40 + 60g Sabouraud broth).

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

The incubation time of the microplate is 24 to 48 hours aerobically.

Trial

For each compound: A = 4- (3-ethoxy-4-hydroxyphenyl) butan-2-one compound B = 1,3-propanediol compound

A 10% (w / v) stock solution was prepared by mixing 1 g of compound in 9 ml of 1% aqueous agar solution. successive dilutions were made with the 1% o agar solution. Test of compounds A and B alone 50 μL of each of the daughter solutions obtained containing compound A or B is added to the wells of the microplate. 100 μl of Sabouraud liquid nutrient broth inoculated with the Aspergillus niger strain and 50 μl of aqueous 1% agar solution are also added.

• Assay of compounds A and B in mixture 50 μΙ of each of the daughter solutions obtained containing compound A and 50 μΙ of each of the daughter solutions obtained containing compound B are added to the wells of the microplate. It also adds 100μΙ of liquid nutrient broth Sabouraud seeded double concentration by the strain Aspergillus niger. Microbial growth control

A positive control of microbial growth has also been realized. The positive microbial growth control corresponds to the mixture of 100 μΙ of a 1% aqueous solution of agar with 10ΟμΙ of Sabouraud liquid nutrient broth inoculated at double concentration by the Aspergillus niger strain in the absence of the compounds A and B. absorbance of compounds A and B alone

In parallel, an absorbance control of compounds A and B alone was carried out. This control corresponds to 10ΟμΙ of liquid Sabouraud liquid nutrient broth at double concentration + 10ΟμΙ of compound A or B at double concentration.

In all three cases (absorbance control, growth control and test), the final volume present in each well of the microplate is 200 μL.

In both 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 5 cfu / ml in Aspergillus niger.

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

The following results were obtained:

The results obtained show a synergy of the inhibitory activity for the mixtures:

i) 0.025% of A and 1% of B is ratio A / B = 0.025 ii) 0.05% of A and 1% of B is ratio A / B = 0.05 iii) 0.05% of A and 0 , 5% of B is ratio A / B = 0.1 iv) 0.05% of A and 0.25% of B is ratio A / B = 0.2

Claims (7)

1. Antimicrobial mixture comprising 4- (3-ethoxy-4-hydroxyphenyl) butan-2-one and 1,3-propanediol present in amounts such that the weight ratio of 4- {3-ethoxy-4-hydroxy-phenyl) Butan-2-one / 1,3-propanediol ranges from 0.02 to 0.15. 2. antimicrobial mixture according to the preceding claim, characterized in that said weight ratio is from 0.02 to 0.07. 3. antimicrobial mixture according to one of claims 1 or 2, characterized in that it has antimicrobial activity against molds, in particular on Aspergillus niger. 4. A composition comprising, in a physiologically acceptable medium, an antimicrobial mixture according to one of claims 1 to 3. 5. Composition according to the preceding claim, characterized in that it comprises at least one additional ingredient selected from water, oils, polyols having 2 to 10 carbon atoms, gelling agents, surfactants, film-forming polymers, dyestuffs, perfumes, fillers, UV filters, plant extracts, cosmetic and dermatological active agents, and salts. 6. Composition according to one of Claims 4 or 5, characterized in that 4- (3-ethoxy-4-hydroxyphenyl) butan-2-one is present in a content ranging from 0.01% to 5% by weight. , relative to the total weight of the composition, preferably ranging from 0.01% to 3% by weight, and preferably ranging from 0.01 to 2.5% by weight. 7. Use of an antimicrobial blend according to any one of claims 1 to 3 for preserving a composition comprising a physiologically acceptable medium.