WO2003002081A1

WO2003002081A1 - Composition comprising a hydroxydiphenyl ether derivative inhibiting the development of body odours

Info

Publication number: WO2003002081A1
Application number: PCT/FR2002/001790
Authority: WO
Inventors: Serge Forestier; Christophe Courbiere
Original assignee: L'oreal
Priority date: 2001-06-29
Filing date: 2002-05-28
Publication date: 2003-01-09
Also published as: FR2826574A1; FR2826574B1

Abstract

The invention relates to a cosmetic or dermopharmaceutical composition comprising at least one hydroxydiphenyl ether derivative and furthermore at least one compound selected from active deodorants or anti-perspirants. The invention also relates to a method for the treatment of body odours, in particular of the armpit, using the above compositions.

Description

COMPOSITIONS CONTAINING A BΗYDROXYDIPHENYL ETHER DERIVATIVE INHIBITING THE DEVELOPMENT OF BODY ODORS

The subject of the present invention is a cosmetic or dermopharmaceutical composition comprising at least one hydroxydiphenyl ether derivative and also at least one compound chosen from particular deodorant or antiperspirant active agents.

The present invention also relates to a process for treating human body odors and in particular axillary odors with these compositions.

In the cosmetic field, it is well known to use, in topical application, deodorant products containing active substances, of antiperspirant type or of bactericidal type, to reduce, even eliminate, generally unpleasant axillary odors.

Antiperspirants have the effect of limiting sweat flow. They generally consist of aluminum salts which, on the one hand, are irritating to the skin and which, on the other hand, reduce the sweat flow by modifying the cutaneous physiology, which is not satisfactory.

Bactericidal substances inhibit the development of the skin flora responsible for axillary odors.

Among the bactericidal products, the most commonly used is Triclosan (2,4,4'-trichloro-2'-hydroxydiphenylether).

In order to obtain long-term efficacy, we are looking for new products with deodorant action, that is to say products which are capable of modifying, reducing and / or removing or preventing development. body odor (this definition is given in the book "Cosmetic Science and Technology Series" - 1988 / Volume 7 chap.10 - Il le). In patent application EP1053989, the use in cosmetics of hydroxydiphenyl ethers has been cited as antimicrobial active agents in particular for deodorizing the skin, mucous membranes, hair, various materials such as paper, paint. However, the effectiveness of these products is limited and insufficient to ensure lasting inhibition of the development of body odors.

After numerous researches carried out on the question, the Applicant has now discovered, unexpectedly and surprisingly, that compositions associating derivatives of hydroxydiphenyl ethers with specific deodorant or antiperspirant active agents have the property of preventing the development of body sweat odors , without the drawbacks of the active substances previously used in deodorant compositions.

This discovery is the basis of the present invention.

The present invention thus has for first object, a cosmetic or dermopharmaceutical composition containing a) at least one derivative of hydroxydiphenyl ethers of formula (1):

wherein R1, R2, R3 and R4, identical or different, denote Z, OZ, COZ, -COOZ, CONZZ ', C ₆ -C ₃ o aralkyl or C ₇ -C ₄ o alkylaryl or C ₇ -C ₀ optionally substituted by one or more groups chosen from OH, NH ₂ , halogen, carboxy, or C1-C30 carbonyl alkoxy;

Z and Z ′, which may be identical or different, denote H, a linear or branched, cyclic or acyclic, saturated or unsaturated, CrC ₃₀ hydrocarbon radical, interrupted or not by one or more heteroatoms or carbonyl groups, substituted or not by one or more groups chosen from OH, NH ₂ , halogen, carboxy or alkoxy Ci -C30 carbonyl; b) at least one deodorant active agent chosen from water-soluble zinc or manganese salts, dicyclic aromatic halogen compounds, hydroxystilbenes, citric acid esters or 3,7,11 -trimethyldodeca-2,5,10-trienol (farnesol) and / or c) an antiperspirant active agent chosen from aluminum hydroxyhalides, aluminum / zirconium hydroxyhalides, aluminum or zirconium complexes with an amino acid.

A second object of the present invention is also a process consisting in using such a composition to prevent or attenuate the development of body sweat odors.

Among the compounds of formula (1) which can be used according to the present invention, preference is given to:

2,4'-dihydroxy diphenyl ether

2-hydroxy 2'-ethylI diphenyl ether

2-hydroxy 2'-isopropyl diphenyl ether

2-hydroxy 2'-methyl diphenyl ether

2-hydroxy 2'-sec.butyl diphenyl ether

2-hydroxy 2'-tert.butyl diphenyl ether

2-hydroxy 3-butanoyl diphenyl ether

2-hydroxy 3-propanoyl diphenyl ether

2-hydroxy 4-formyl diphenyl ether

2-hydroxy 4'-methyl 5-formyl diphenyl ether

2-hydroxy 5-butanoyl diphenyl ether

2-hydroxy 5-formyl diphenyl ether

2-hydroxy diphenyl ether

3-hydroxy 2'-methyl diphenyl ether

3-hydroxy 2'-sec.butyl diphenyl ether

3-hydroxy 2'-methyl 4-n-propyl diphenyl ether

3-hydroxy 3'-methyl diphenyl ether

3-hydroxy 3'-methyl 4-n-propyl diphenyl ether 3-hydroxy 4- (1-hydroxy 2-methylρropyl) diphenyl ether

3-hydroxy 4-butanoyl diphenyl ether

3-hydroxy 4-butyl diphenyl ether

3-hydroxy 4-dimethylpropyl diphenyl ether

3-hydroxy 4-dimethylpropyl 3'-methyl diphenyl ether

3-hydroxy 4-hexyl diphenyl ether

3-hydroxy 4-hexanoyl diphenyl ether

3-hydroxy 4-dodecyl diphenyl ether

3-hydroxy 4-isobutanoyl diphenyl ether

3-hydroxy 4-isobutyl diphenyl ether

3-hydroxy 4-isopentanoyl diphenyl ether

3-hydroxy 4-isopropyl diphenyl ether

3-hydroxy 4'-isopropyl diphenyl ether

3-hydroxy 4-n-butyl diphenyl ether

3-hydroxy 4-n-pentyl diphenyl ether

3-hydroxy 4-n-propyl diphenyl ether

3-hydroxy 4-pentanoyl diphenyl ether

3-hydroxy 4-pentyl diphenyl ether

3-hydroxy 4-phenylethyl diphenyl ether

3-hydroxy 2'-methyl 4-phenylethyl diphenyl ether

3-hydroxy 3'-methyl 4-phenylethyl diphenyl ether

3-hydroxy 4-propanoyl diphenyl ether

3-hydroxy diphenyl ether

3,4'-dihydroxy diphenyl ether

4,4'-dihydroxy diphenyl ether

4-hydroxy 2'-methyl 5'-isopropyl diphenyl ether

4-hydroxy 2'-tert.butyl 5'-methyl diphenyl ether

4-hydroxy 2 ', 5'-dimethyl diphenyl ether

4-hydroxy 2'-cyclohexyl 5'-methyl diphenyl ether

4-hydroxy 2'-isopropyl 4'-ethyl diphenyl ether

4-hydroxy 2'-isopropyl 4'-propyl diphenyl ether

4-hydroxy 2'-isopropyl 5'-methyl diphenyl ether 4-hydroxy 2'-isopropyl diphenyl ether

4-hydroxy 2'-isopropyl 4'-phenylethyl diphenyl ether

4-hydroxy 3- (3-methylbutyl) 4 '- (3-methylbutyl) diphenyl ether

4-hydroxy 4'-dimethylpropyl diphenyl ether

4-hydroxy 4'-ethyl diphenyl ether

4-hydroxy 4'-nonyl diphenyl ether

4-hydroxy 4'-phenylethyl diphenyl ether

4-hydroxy 4'-propyl diphenyl ether

4-hydroxy 4'-trifluoromethyl diphenyl ether

4-hydroxy 4'-propanoyl diphenyl ether

4-hydroxy diphenyl ether

Even more preferably, 4,4'-dihydroxydiphenyl ether will be used.

In the compositions of the invention, the concentration of compound (s) of formula (1) preferably varies from 0.001 to 20% by weight, more preferably from 0.01 to 15% by weight and even more preferably from 0.1 to 10% by weight. weight relative to the total weight of the composition.

Among the deodorant active agents (b) according to the invention, there may be mentioned for example, zinc pyrrolidone carboxylate (more commonly called zinc pidolate), zinc sulphate, zinc chloride, zinc lactate, zinc gluconate and zinc phenolsulfonate, 2,4,4 ^, -trichloro-2'-hydroxydiphenylether (Triclosan), 2,4-dichloro-2'-hydroxydiphenylether, 3 ', 4', 5'-trichlorosalicylanilide, la 1 - (3 ', 4'- dichlorophenyl) -3- (4'-chlorophenyl) urea (triclocarban) or 3,7,11-trimethyldodeca-2,5,10-trienol (Famesol).

Among the antiperspirant active agents (c) there may be mentioned for example aluminum hydrochloride, aluminum chlorohydrex, aluminum chlorohydrex PEG, aluminum chlorohydrex PG, aluminum dichlorohydrate, aluminum dichlorohydrex PEG, aluminum dichlorohydrex PG, aluminum sesquichlorohydrate, aluminum sesquichlorohydrex PEG, aluminum sesquichlorohydrex PG, aluminum sulfate, aluminum zirconium octachlorohydrate, aluminum zirconium pentachlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium trichlorohydrate, metal complexes (such as aluminum or zirconium) with an amino acid and as described in patent US-3792068. Such complexes are generally known by the name ZAG. ZAG complexes usually have an Al / Zr quotient ranging from approximately 1.67 to 12.5 and a Metal / Cl quotient ranging from approximately 0.73 to 1.93.

The preferred amino acid for preparing such ZAG complexes is glycine. Among these products, mention may be made of aluminum zirconium octachlorohydrex GLY, aluminum zirconium pentachlorohydrex GLY, aluminum zirconium tetrachlorohydrate GLY and aluminum zirconium trichlorohydrate-GLY.

These deodorant (b) or antiperspirant (c) active agents are preferably present in the composition according to the invention in an amount of approximately 0.001 to 20% by weight relative to the total weight of the composition, and more preferably in an amount of approximately 0.1 to 10% by weight.

The cosmetic composition according to the invention is conventionally formulated according to the form of presentation for which it is intended.

It is more particularly formulated in a cosmetically acceptable vehicle which can in particular be essentially aqueous, or contain organic solvents and in particular monoalcohols in CrC ₄ , preferably ethanol to accelerate the evaporation of the product, or propylene glycol, dipropylene glycol or their ethers.

The cosmetic composition according to the invention can also be formulated as a water-in-oil emulsion, oil-in-water, or as a triple water-in-oil-in-water emulsion (such emulsions are known and described for example by C. FOX in "Cosmetics and Toiletries" - November 1986 - Vol 101 - pages 101-112).

The cosmetic composition according to the invention can also comprise cosmetic adjuvants chosen from fatty substances, gelling agents, emollients, softeners, antioxidants, opacifiers, stabilizers, anti-foaming agents, moisturizing agents, vitamins, perfumes, preservatives, surfactants, fillers, sequestrants, polymers, propellants, basifying or acidifying agents, perfumes, dyes, pigments, thickening agents, or any other ingredient usually used in cosmetics for this type of application.

Of course, the person skilled in the art will take care to choose this or these optional additional compounds in such a way that the advantageous properties intrinsically attached to the cosmetic composition in accordance with the invention are not, or substantially not, impaired by the addition (s) envisaged. .

The surfactants are preferably chosen from anionic, amphoteric or nonionic surfactants.

The fatty substances may consist of an oil or a wax or their mixture, petrolatum, paraffin, lanolin, hydrogenated lanolin, acetylated lanolin; they also include fatty acids, fatty alcohols such as lauric, cetyl, myristic, stearic, palmitic, oleic alcohol as well as 2-octyldodecanol, fatty acid esters such as glycerol monostearate, polyethylene glycol monostearate , isopropyl myristate, isopropyl adipate, isopropyl palmitate, octyl palmitate, C12-C15 fatty alcohol benzoates (Finsolv TN from FINETEX), polyoxypropylenated myristic alcohol at 3 moles of propylene oxide (WITCONOL APM from WITCO), triglycerides of fatty acids CQ-C ^ Q such as triglycerides of caprylic / capric acid.

The oils are chosen from animal, vegetable, mineral or synthetic oils and in particular hydrogenated palm oil, hydrogenated castor oil, petroleum jelly oil, paraffin oil, Purcellin oil (octanoate stearyl), silicone oils and isoparaffins.

The waxes are chosen from animal, fossil, vegetable, mineral or synthetic waxes. Mention may in particular bees beeswax, Camauba waxes, Candellila, sugar cane, Japan, ozokerites, ontan wax, microcrystalline waxes, paraffins, waxes and silicone resins.

The thickeners, preferably nonionic, can be chosen from guar gums and modified or unmodified celluloses such as hydroxypropylated guar gum, cetylhydroxyethylcellulose, silicas such as, for example, Bentone Gel MiO sold by the company NL INDUSTRIES or Veegum Ultra, sold by the company POLYPLASTIC.

The cosmetic composition can comprise emollients, which contribute to a soft, dry feeling, non-sticky when the composition is applied to the skin. These emollients can be chosen from products of the volatile silicone type, non-volatile silicones and other non-volatile emollients.

Volatile silicones are defined in a known manner as volatile compounds at room temperature. Among these compounds, mention may be made of cyclic and linear volatile silicones of the dimethylsiloxane type, the chains of which comprise from 3 to 9 silicone residues. Preferably, cyclomethicones D4 or D5 are chosen.

Non-volatile silicones are defined in a known manner as compounds with low vapor pressure at room temperature. Among these compounds are included: polyalkylsiloxanes, in particular linear polyalkylsiloxanes such as, for example, linear polydimethylsiloxanes, or dimethicones, sold by the company Dow Corning under the name of "Dow Corning 200 Fluid"; polyalkylaryisiloxanes such as, for example, polymethylphenylsiloxanes, sold by the company Dow Corning under the name of "Dow Corning 556 Fluid"; polyether and siloxane copolymers, such as, for example, dimethicone copolyols.

Among the non-volatile emollients useful in the present invention include for example: hydrocarbon-based derivatives, mineral oils, fatty alcohols, alcohol esters of C ₃ -Cι ₈ with acids C ₃ -Cι ₈ , esters of benzoic acid with C ₁₂ -C ₁₈ alcohols and their mixtures, polyols in C2-C ₆ preferably chosen from glycerol, propylene glycol or sorbitol, polymers of polalkylene glycol.

The amounts of these various constituents which may be present in the cosmetic composition according to the invention are those conventionally used for the forms of presentation considered.

The cosmetic composition according to the invention can thus be in the form of a lotion, cream or fluid gel distributed in aerosol spray, in pump bottle or in roll-on, in the form of thick cream distributed in tube and in the form of stick or powder, and contain in this regard the ingredients and propellants generally used in this type of product and well known to those skilled in the art.

Concrete, but in no way limiting, examples illustrating the invention will now be given.

EXAMPLE 1: Roll on deodorant

Cetylstearyl alcohol (NAFOL 1618F from CONDEA) 2.5 g Cetylstearyl alcohol at 33 moles OE (EMULDAC AS 25 from CONDEA) 1.25 g Sorbitan monostearate (TWEEN 60 from ICI) 2.2 g

Stearyl alcohol (ACILOL 18 from AEGIS CHEMICAL) 0.3 g

Isohexadecane 6.0 g

Propylene glycol 3.0 g

4,4'-dihydroxy diphenyl ether 2.0 g Faresol 0.5 g

Preservatives qs

Demineralized water qs 100.0 g

EXAMPLE 2 Stick Laurylmethicone copolyol (Q2-5200 Formulation Aid from DOW CORNING) 5.0g Cyclohexadimethylsiloxane

(DOW CORNING 246 FLUID from DOW CORNING) 22.5 g

Hydrogenated castor oil 12.5 g

4,4'-dihydroxydiphenylether 2.0 g Aluminum hydrochloride 1.5 g

Antioxidants qs

Demineralized water qs 100.0 g

Claims

1. Cosmetic or dermopharmaceutical composition, characterized in that it contains: a) at least one derivative of hydroxydiphenyl ethers of formula (1):

in which R1, R2, R3 and R4, identical or different, denote Z, OZ, COZ, COOZ, CONZZ ', C ₆ -C ₃ aryl or C ₇ -C ₀ aralkyl or C ₇ -C ₄₀ alkyaryl optionally substituted by one or more groups chosen from OH,

NH ₂ , halogen, carboxy, or alkoxy C1 -C30 carbonyl;

Z and Z ', identical or different, denote H, a linear or branched C ₁ -C ₃₀ hydrocarbon radical, cyclic or acyclic, saturated or unsaturated, interrupted or not interrupted by one or more heteroatoms or carbonyl groups, substituted or not by one or more groups chosen from OH, NH ₂ , halogen, carboxy or alkoxy

C1-C30 carbonyl; b) at least one deodorant active agent chosen from water-soluble zinc or manganese salts, dicyclic aromatic halogen compounds, hydroxystilbenes, citric acid esters or 3,7,11-trimethyldodeca-2,5,10-trienol (famesol). and / or c) an antiperspirant active agent chosen from aluminum hydroxyhalides, aluminum / zirconium hydroxyhalides, aluminum or zirconium complexes with an amino acid.

2. Composition according to Claim 1, characterized in that the compound of formula (1) is chosen from the following compounds:

2,4'-dihydroxy diphenyl ether

2-hydroxy 2'-ethyl diphenyl ether

2-hydroxy 2'-isopropyl diphenyl ether 2-hydroxy 2'-methyl diphenyl ether

2-hydroxy 2'-sec.butyl diphenyl ether

2-hydroxy 2'-tert.butyl diphenyl ether

2-hydroxy 3-butanoyl diphenyl ether

2-hydroxy 3-propanoyl diphenyl ether

2-hydroxy 4-formyl diphenyl ether

2-hydroxy 4'-methyl 5-formyl diphenyl ether

2-hydroxy 5-butanoyl diphenyl ether

2-hydroxy 5-formyl diphenyl ether

2-hydroxy diphenyl ether

3-hydroxy 2'-methyl diphenyl ether

3-hydroxy 2'-sec.butyl diphenyl ether

3-hydroxy 2'-methyl 4-n-propyl diphenyl ether

3-hydroxy 3'-methyl diphenyl ether

3-hydroxy 3'-methyl 4-n-propyl diphenyl ether

3-hydroxy 4- (1-hydroxy 2-methylpropyl) diphenyl ether

3-hydroxy 4-butanoyl diphenyl ether

3-hydroxy 4-butyl diphenyl ether

3-hydroxy 4-dimethylpropyl diphenyl ether

3-hydroxy 4-dimethylpropyl 3'-methyl diphenyl ether

3-hydroxy 4-hexyl diphenyl ether

3-hydroxy 4-hexanoyl diphenyl ether

3-hydroxy 4-dodecyl diphenyl ether

3-hydroxy 4-isobutanoyl diphenyl ether

3-hydroxy 4-isobutyl diphenyl ether

3-hydroxy 4-isopentanoyl diphenyl ether

3-hydroxy 4-isopropyl diphenyl ether

3-hydroxy 4'-isopropyl diphenyl ether

3-hydroxy 4-n-butyl diphenyl ether

3-hydroxy 4-n-pentyl diphenyl ether

3-hydroxy 4-n-propyl diphenyl ether

3-hydroxy 4-pentanoyl diphenyl ether 3-hydroxy 4-pentyl diphenyl ether

3-hydroxy 4-phenylethyl diphenyl ether

3-hydroxy 2'-methyl 4-phenylethyl diphenyl ether

3-hydroxy 3'-methyl 4-phenylethyl diphenyl ether

3-hydroxy 4-propanoyl diphenyl ether

3-hydroxy diphenyl ether

3,4'-dihydroxy diphenyl ether

4,4'-dihydroxy diphenyl ether

4-hydroxy 2'-methyl 5'-isopropyl diphenyl ether

4-hydroxy 2'-tert.butyl 5'-methyl diphenyl ether

4-hydroxy 2 ', 5'-dimethyl diphenyl ether

4-hydroxy 2'-cyclohexyl 5'-methyl diphenyl ether

4-hydroxy 2'-isopropyl 4'-ethyl diphenyl ether

4-hydroxy 2'-isopropyl 4'-propyl diphenyl ether

4-hydroxy 2'-isopropyl 5'-methyl diphenyl ether

4-hydroxy 2'-isopropyl diphenyl ether

4-hydroxy 2'-isopropyl 4'-phenylethyl diphenyl ether

4-hydroxy 3- (3-methylbutyl) 4 '- (3-methylbutyl) diphenyl ether

4-hydroxy 4'-dimethylpropyl diphenyl ether

4-hydroxy 4'-ethyl diphenyl ether

4-hydroxy 4'-nonyl diphenyl ether

4-hydroxy 4'-phenylethyl diphenyl ether

4-hydroxy 4'-propyl diphenyl ether

4-hydroxy 4'-trifluoromethyl diphenyl ether

4-hydroxy 4'-propanoyl diphenyl ether

4-hydroxy diphenyl ether

3. Composition according to any one of claims 1 or 2, characterized in that the concentration of compound (s) of formula (1) varies from 0.001 to 20%, preferably from 0.01 to 15% and still preferably from 0.1 to 10% of the total weight of the composition.

4. Composition according to any one of claims 1 to 3, characterized in that the deodorant active agents (b) are chosen from pyrrolidone carboxylate zinc (more commonly known as zinc pidolate), zinc sulfate, zinc chloride, zinc lactate, zinc gluconate and zinc phenolsulfonate, 2,4,4'-trichloro-2'-hydroxydiphenylether (Triclosan), 2,4-dichloro-2'- hydroxydiphenylether, 3 ', 4', 5'-trichlorosalicylanilide, 1- (3 ', 4'-dichlorophenyl) -3- (4'-chlorophenyl) urea (triclocarban) or 3,7,11-trimethyldodeca-2,5,10-trienol (Famesol).

5. Composition according to any one of claims 1 to 3, characterized in that the active antiperspirant (c) are selected from aluminum chlorohydrate, aluminum chlorohydrex, aluminum chlorohydrex _PEG. aluminum chlorohydrex PG, aluminum dichlorohydrate, aluminum dichlorohydrex PEG, aluminum dichlorohydrex PG, aluminum sesquichlorohydrate, aluminum sesquichlorohydrex PEG, aluminum sesquichlorohydrex PG, aluminum sulfate, aluminum zirconium octachlorohydrate , aluminum zirconium pentachlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium trichlorohydrate, metal complexes with an amino acid

6. Composition according to claim 5, characterized in that the amino acid used with the metal complexes is glycine.

7. Composition according to claim 6, characterized in that the complexes are chosen from aluminum zirconium octachlorohydrex GLY, aluminum zirconium pentachlorohydrex GLY, aluminum zirconium tetrachlorohydrate GLY and aluminum zirconium trichlorohydrate-GLY.

8. Composition according to any one of claims 1 to 7, characterized in that the deodorant active agents (b) or antiperspirant (c) are present in an amount of about 0.001 to 20% by weight relative to the total weight of the composition.

9. Composition according to Claim 8, characterized in that the deodorant (b) or antiperspirant (c) active agents are present in an amount of approximately 0.1 to 10% by weight relative to the total weight of the composition.

10. Composition according to any one of claims 1 to 9, characterized in that it formulated in a cosmetically acceptable vehicle which contains water and / or one or more organic solvents.

11. Composition according to Claim 10, characterized in that the organic solvent is chosen from CrC monoalcohols, propylene glycol, dipropylene glycol or their ethers.

12. Composition according to claim 11, characterized in that the organic solvent is ethanol.

13. Composition according to any one of claims 1 to 12, characterized in that it is formulated in the form of a water-in-oil emulsion, oil-in-water, or a triple water-in-oil emulsion -in-water

14. Composition according to any one of claims 1 to 13, characterized in that it contains one or more cosmetic adjuvants chosen from fatty substances, gelling agents, emollients, softeners, antioxidants, opacifiers, stabilizers, anti-foaming agents, moisturizing agents, vitamins, perfumes, preservatives, surfactants, fillers, sequestrants, polymers, propellants, basifying or acidifying agents, perfumes, dyes, pigments, thickening agents, or any other ingredient usually used in cosmetics.

15. Composition according to any one of claims 1 to 14, characterized in that it is in the form of a lotion, cream or fluid gel distributed in aerosol spray, in pump bottle or in roll-on, in the form thick cream distributed in a tube and in the form of a stick or powder.

16. A method for preventing or attenuating the development of body sweat odors, characterized in that it consists in using a composition according to any one of claims 1 to 15.