WO2007031117A1 - Use op a lipophilic salicylic acid derivative as a deodorant active agent, process for treating body odour - Google Patents

Use op a lipophilic salicylic acid derivative as a deodorant active agent, process for treating body odour Download PDF

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WO2007031117A1
WO2007031117A1 PCT/EP2006/003302 EP2006003302W WO2007031117A1 WO 2007031117 A1 WO2007031117 A1 WO 2007031117A1 EP 2006003302 W EP2006003302 W EP 2006003302W WO 2007031117 A1 WO2007031117 A1 WO 2007031117A1
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formula
acid
carbon atoms
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PCT/EP2006/003302
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Cyril Lemoine
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L'oreal
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Priority claimed from FR0550989A external-priority patent/FR2884416B1/en
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Publication of WO2007031117A1 publication Critical patent/WO2007031117A1/en

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00Anti-perspirants or body deodorants

Definitions

  • Aluminium salts These active agents are the ones most commonly used as antiperspirant active agents. The principle of action of these active agents is to form a gel in the sweat duct. This gel creates a plug that partially blocks the sweat pores. The flow of sweat is thus reduced. These aluminium salts also have intrinsic efficacy since they are antibacterial. They thus also have a direct role on the deodorant efficacy by reducing the number of bacteria responsible for the degradation of sweat.
  • the lipophilic salicylic acid derivatives of formula (I) of the invention which will be defined later, are known in patent FR 2 581 542 for treating skin of keratolytic and/or comedolytic type. These derivatives have good antibacterial activity on the Propionibacterium strains involved in acne.
  • R represents a chain derived from linoleic acid, linolenic acid or oleic acid.
  • the waxes may be chosen from animal, fossil, plant, mineral and synthetic waxes. Mention may be made especially of beeswax, carnauba wax, candelilla wax, sugar cane wax, Japan wax, ozokerites, montan wax, microcrystalline waxes, paraffins and silicone waxes and resins.
  • the thickeners which are preferably nonionic, may be chosen from modified or unmodified guar gums and celluloses, such as hydroxypropyl guar gum or cetylhydroxyethylcellulose, silicas, for instance Bentone Gel MIO sold by the company NL Industries, or Veegum Ultra sold by the company Polyplastic.
  • results are expressed, for each microorganism tested, as the Log number of reduction after 24 hours relative to the placebo: identical results: none,

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  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
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Abstract

The present invention relates to the cosmetic use of at least one lipophilic salicylic acid derivative of formula (I) below, or a salt thereof : as deodorant agent in a deodorant cosmetic composition not containing antiperspirant agent. The invention also relates to a cosmetic process for treating human perspiration and human body odour, in particular underarm perspiration and underarm odour, which consists in applying a deodorant composition comprising at least one lipophilic salicylic acid derivative of formula (I) below, or a salt thereof derived from a mineral base, and containing no antiperspirant active agent.

Description

USE OF A LIPOPHILIC SALICYLIC ACID DERIVATIVE AS A DEODORANT ACTIVE AGENT, PROCESS FOR TREATING BODY ODOUR
5 The present invention relates to the cosmetic use of at least one lipophilic salicylic acid derivative of particular chemical structure as a deodorant agent in a deodorant cosmetic composition not containing antiperspirant agent.
10 The invention also relates to a cosmetic process for treating human perspiration and human body odour, in particular underarm perspiration and underarm odour, which consists in applying a deodorant composition comprising at least one lipophilic
15 salicylic acid derivative of formula (I) below, or a salt thereof derived from a mineral base, and containing no antiperspirant active agent.
Eccrine or apocrine sweat has little odour when it is secreted. It is the degradation of this
20 sweat by bacteria via enzymatic reactions that produces malodorous compounds. The function of deodorant active agents is to reduce or prevent the formation of unpleasant odours. The various systems proposed to date may be grouped in major families.
25 (i) Bactericidal substances or substances that limit bacterial growth:
There are bactericidal substances that destroy the resident bacterial flora. Among these substances, the one most widely used is Triclosan (2, 4, 4' -trichloro-2' -hydroxydiphenyl ether), which has the drawback of substantially modifying the ecology of the cutaneous flora. There are substances that reduce bacterial growth. Among these substances, mention may be made of transition-metal-chelating agents, for instance EDTA or DPTA. These materials deprive the medium of the metals required for the growth of the bacteria. These active agents are, unfortunately, potentially ecotoxic and can cause environmental problems .
(ii) Substances that block the enzymatic reactions responsible for the formation of odoriferous compounds: Particular examples that may be mentioned include arylsulfatase inhibitors, 5-lipoxygenase inhibitors, aminocyclase inhibitors and β-glucuronidase inhibitors. Unfortunately, these inhibitors are often specific and thus of relatively poor efficacy compared with antibacterial agents. (iii) Unpleasant-odour absorbers:
These odour absorbers "capture" or reduce the volatility of odoriferous compounds. Odour absorbers that may be mentioned include zeolites and cyclodextrins. These compounds are difficult to formulate since the compounds of the formula may interact and reduce their efficacy. Furthermore, the absorption is often selective, which limits the efficacy of these compositions. Eccrine sweat is secreted to enable thermolysis during body heat disequilibria caused by effort or external heat. This sweat is responsible for the sensations of moisture and for the ring stains on clothing. Antiperspirant products were developed to avoid these unpleasant phenomena.
Several types of antiperspirant active agent exist :
(a) Moisture absorbers: The object of moisture absorbers is to capture sweat at the surface of the skin. Perspiration takes place, but the unpleasant phenomena associated therewith are avoided (panty liner principle) . The moisture absorbers known in the prior art that may be mentioned include superabsorbent polymers of starch type grafted with homopolymers and copolymers of a sodium salt of poly (2-propenamide-co-propenoic acid) as described in patent application WO 03/030 853.
(b) Film-forming agents: The principle of film-forming agents is to form a film at the surface of the skin that is sufficiently uniform to partially block the sweat ducts and thus prevent the sweat from being secreted.
(c) Aluminium salts: These active agents are the ones most commonly used as antiperspirant active agents. The principle of action of these active agents is to form a gel in the sweat duct. This gel creates a plug that partially blocks the sweat pores. The flow of sweat is thus reduced. These aluminium salts also have intrinsic efficacy since they are antibacterial. They thus also have a direct role on the deodorant efficacy by reducing the number of bacteria responsible for the degradation of sweat.
With the aim of obtaining long-term efficacy, there is a need to find better combinations of active agents . The lipophilic salicylic acid derivatives of formula (I) of the invention, which will be defined later, are known in patent FR 2 581 542 for treating skin of keratolytic and/or comedolytic type. These derivatives have good antibacterial activity on the Propionibacterium strains involved in acne.
The combination of a lipophilic salicylic acid derivative of formula (I) with an antiperspirant active agent was suggested in patent application WO 97/15278, which describes the cosmetic use of a substance P antagonist as an antiperspirant agent and the possibility of adding as a lipophilic additive a salicylic acid derivative into these antiperspirant formulations .
The combination of a lipophilic salicylic acid derivative with an antiperspirant active agent has also been mentioned in patent application WO 04/073 745. The said document describes the efficacy-boosting effect of these salicylic acid derivatives on 48 types of cosmetic active agent, among which are mentioned, without specifying their nature, antiperspirant active agents.
The Applicant has discovered, surprisingly and unexpectedly, that the particular lipophilic salicylic acid derivatives of formula (I) as defined later show good intrinsic deodorant activity without modifying the natural flow of perspiration and do not have the drawbacks of the other known deodorant active agents mentioned previously.
The applicant has also found that these same lipophilic salicylic acid derivatives show lower bactericidal activity than Triclosan and thus better respect the cutaneous flora. For the purposes of the present invention, the term "deodorant agent" means any compound capable of producing a reduction in the unpleasant odours associated with the degradation of sweat.
One subject of the present invention is thus the use of at least one lipophilic salicylic acid derivative of particular chemical structure as a deodorant active agent in a deodorant cosmetic composition not containing antiperspirant agent.
The invention also relates to a cosmetic process for treating human perspiration and human body odour, in particular underarm perspiration and underarm odour, which consists in applying a deodorant composition comprising at least one lipophilic salicylic acid derivative of formula (I) below, or a salt thereof, and not containing antiperspirant active agent .
Other subjects of the invention will be described later.
For the purposes of the present invention, the term "deodorant composition" means any composition capable of masking, absorbing, improving and/or reducing the unpleasant odour resulting from the decomposition of human sweat by bacteria.
The term "antiperspirant active agent" means any substance that has the effect of reducing the flow of sweat.
The term "composition not containing antiperspirant active agent" means any composition containing less than 1% and preferably less than 0.1% by weight of antiperspirant active agent relative to the total weight of the composition.
The term "lipophilic salicylic acid derivative" means any compound in its acid form whose solubility in water at 25°C is less than 1%.
The lipophilic salicylic acid derivatives in accordance with the invention correspond to formula (I):
Figure imgf000008_0001
in which:
- the radical R denotes a linear, branched or cyclic, saturated aliphatic chain containing from 2 to 22 carbon atoms; an unsaturated chain containing from 2 to 22 carbon atoms containing one or more double bonds that may be conjugated; an aromatic nucleus linked to the carbonyl radical directly or via saturated or unsaturated aliphatic chains containing from 2 to 7 carbon atoms; the said groups possibly being substituted with one or more substituents, which may be identical or different, chosen from (a) halogen atoms, (b) a trifluoromethyl group, (c) hydroxyl groups in free form or esterified with an acid containing from 1 to 6 carbon atoms, or (d) a carboxyl function in free form or esterified with a lower alcohol containing from 1 to 6 carbon atoms;
- R' is a hydroxyl group or ester group of formula:
Figure imgf000008_0002
in which R1 denotes a linear or branched, saturated or unsaturated aliphatic chain containing from 1 to 18 carbon atoms; and also salts thereof derived from a mineral base.
The lipophilic salicylic acid derivatives of formula (I) that may be used according to the invention are described in patents US 6 159 479 and US 5 558 871, FR 2 581 542, US 4 767 750, EP 378 936, US 5 267 407, US 5 667 789, US 5 580 549 and EP-A-570 230.
Preferentially, the radical R denotes a linear, branched or cyclic, saturated aliphatic chain containing from 3 to 11 carbon atoms; an unsaturated chain containing from 3 to 17 carbon atoms and comprising one or more conjugated or unconjugated double bonds; the said hydrocarbon-based chains possibly being substituted with one or more substituents, which may be identical or different, chosen from (a) halogen atoms, (b) a trifluoromethyl group, (c) hydroxyl groups in free form or esterified with an acid containing from 1 to 6 carbon atoms, or (d) a carboxyl function in free form or esterified with a lower alcohol containing from 1 to 6 carbon atoms; - R' is a hydroxyl group or ester group of formula:
—0-C-R1
Il O in which Ri denotes a -0- (C=O) - (CH2) n~CH3 radical in which n is a number ranging from 0 to 14; and also salts thereof obtained by salification with a mineral base.
The compounds that are more particularly preferred are those in which the radical R is a Ca-Cn alkyl group and R' denotes hydroxyl.
Other compounds that are particularly advantageous are those in which R represents a chain derived from linoleic acid, linolenic acid or oleic acid.
Another group of compounds that are particularly preferred consists of compounds in which the radical R denotes a C3-C11 alkyl group bearing a carboxyl function in free form or esterified with a lower alcohol containing from 1 to 6 carbon atoms and R' denotes hydroxyl.
Among the compounds of formula (I) that are particularly preferred, mention may be made of: 5-n-octanoylsalicylic acid (or capryloylsalicylic acid) ; 5-n-decanoylsalicylic acid; 5-n-dodecanoyl- salicylic acid; 5-n-heptyloxysalicylic acid, and the corresponding salts thereof.
5-n-Octanoylsalicylic acid (or capryloylsalicylic acid) manufactured under the trade name Mexoryl SAB by the company Chimex (see page 139 of the International Cosmetic Ingredient Dictionary, 6th edition, Volume 1, published by the review Cosmetic Toiletries and Fragrance Association, 1995) will be used more particularly. The salts of the lipophilic salicylic acid derivatives of formula (I) are obtained by salification with a mineral base. Examples of mineral bases that may be used preferably include alkali metal or alkaline- earth metal hydroxides, for instance sodium hydroxide or potassium hydroxide.
In the compositions of the invention, the concentration of salicylic compound of formula (I) preferably ranges from 0.001% to 20%, more preferentially from 0.01% to 15% and even more preferentially from 0.05% to 5% by weight relative to the total weight of the composition.
The deodorant compositions according to the invention intended for cosmetic use may be in the form of lotions, creams or fluid gels distributed as an aerosol spray, in a pump-dispenser bottle or as a roll- on, in the form of thick creams distributed in tubes or a grille; in the form of wands (sticks) , and may contain in this regard the ingredients generally used in products of this type and well known to those skilled in the art, provided that they do not interfere with the lipophilic salicyclic acid derivative (s) described in the present invention. The deodorant compositions according to the present invention intended for cosmetic use may comprise at least one aqueous phase. They are especially formulated as aqueous lotions or as water- in-oil, oil-in-water emulsions, or as multiple emulsions (oil-in-water-in-oil or water-in-oil-in-water triple emulsions (such emulsions are known and described, for example, by CF. Fox in "Cosmetics and Toiletries", November 1986, Vol. 101, pages 101-112)). The aqueous phase of the said compositions contains water and generally other water-soluble or water-miscible solvents. The water-soluble or water- rniscible solvents include short-chain monoalcohols, for example of C1-C4, for instance ethanol or isopropanol; diols or polyols, for instance ethylene glycol, 1,2- propylene glycol, 1,3-butylene glycol, hexylene glycol, diethylene glycol, dipropylene glycol, 2-ethoxyethanol, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether and sorbitol. Propylene glycol and glycerol will more particularly be used.
According to one particular form of the invention, the deodorant compositions may be anhydrous. For the purposes of the invention, the term "anhydrous" refers to a composition whose content of free or added water is less than 3% and preferably whose content of added water is less than 1% by weight relative to the total weight of the composition.
The compositions according to the invention preferably comprise at least one water-immiscible organic liquid phase. This phase generally comprises one or more hydrophobic compounds that render the said phase water-immiscible. The said phase is liquid (in the absence of a structuring agent) at room temperature (20-250C) . The water-immiscible organic liquid phase in accordance with the invention generally consists of an oil or a mixture of oils and comprises at least 80% of compounds with a vapour pressure not exceeding 4 kPa ( 30 mmHg) at 250C .
The water-immiscible organic liquid phase preferably contains one or more volatile or nonvolatile, silicone-based or hydrocarbon-based emollient oils. These emollient oils are especially described in patents US 4 822 596 and US 4 904 463.
Volatile silicones are defined, in a known manner, as being compounds that are volatile at room temperature. Mention may be made among these compounds of cyclic and linear volatile silicones of the dimethylsiloxane type whose chains comprise from 3 to 9 silicone-based residues. Cyclomethicones D4, D5 or D6 are preferably chosen.
Non-volatile silicones are defined, in a known manner, as being compounds with a low vapour pressure at room temperature. The following are included among these compounds: polyalkylsiloxanes, in particular linear polyalkylsiloxanes, for instance the linear polydimethylsiloxanes, or dimethicones, sold by the company Dow Corning under the name "Dow Corning 245 Fluid"; polyalkylarylsiloxanes, for instance the polymethylphenylsiloxanes sold by the company Dow Corning under the name "Dow Corning 556 Fluid"; copolymers of polyether and siloxane, for instance dimethicone copolyols.
Among the non-volatile emollient oils that may be used in the present invention, examples that may be mentioned include: hydrocarbon-based derivatives, mineral oils, fatty alcohols, esters of C3-C18 alcohols with C3-C18 acids, esters of benzoic acid with Ci2-CiS alcohols and mixtures thereof, C2-C6 polyols preferably chosen from glycerol, propylene glycol or sorbitol, polyalkylene glycol polymers.
The emollient oils are preferably present in amounts ranging from 1% to 50% by weight and more preferably from 5% to 40% by weight relative to the total weight of the composition. The deodorant cosmetic composition according to the invention may contain one or more additional deodorant active agents, for instance bacteriostatic agents or bactericidal agents such as 2, 4, 4' -trichloro- 2' -hydroxydiphenyl ether (Triclosan) , 2, 4-dichloro-2' - hydroxydiphenyl ether, 3',4',5'- trichlorosalicylanilide, 1- (3' , 4' -dichlorophenyl) -3- (4' -chlorophenyl) urea (Triclocarban) or 3,7,11- trimethyldodeca-2, 5, 10-trienol (Farnesol); quaternary ammonium salts, for instance cetyltrimethylammonium salts or cetylpyridinium salts; chlorhexidine and salts; diglyceryl monocaprate, diglyceryl monolaurate or glyceryl monolaurate; polyhexamethylene biguanide salts.
In order to improve the homogeneity of the product, it is possible also to use one or more suspension agents preferably chosen from hydrophobic- modified montmorillonite clays, for instance hydrophobic-modified bentonites or hectorites. Examples that may be mentioned include the product stearalkonium bentonite (CTFA name) (product of reaction of bentonite and the quaternary ammonium stearalkonium chloride) , such as the commercial product sold under the name Tixogel MP 250 by the company Sϋd Chemie Rheologicals, United Catalysts Inc. or the product disteardimonium hectorite (CTFA name) (product of reaction of hectorite and of distearyldimonium chloride) sold under the name Bentone 38 or Bentone Gel by the company Elementis Specialities.
The suspension agents are preferably present in amounts ranging from 0.1% to 5% by weight and more preferentially from 0.2% to 2% by weight relative to the total weight of the composition. The compositions according to the invention may also contain at least one organic powder.
Among the fillers that may be used according to the invention, mention may be made of organic powders. In the present patent application, the term "organic powder" means any solid that is insoluble in the medium at room temperature (25°C) .
As organic powders that may be used in the composition of the invention, examples that may be mentioned include polyamide particles and especially those sold under the name Orgasol by the company
Atochem; polyethylene powders; microspheres based on acrylic copolymers, such as those made of ethylene glycol dimethacrylate/lauryl methacrylate copolymer, sold by the company Dow Corning under the name Polytrap; polymethyl methacrylate microspheres, sold under the name Microsphere M-100 by the company Matsumoto or under the name Covabead LH85 by the company Wackherr; ethylene-acrylate copolymer powders, for instance those sold under the name Flobeads by the company Sumitomo Seika Chemicals; expanded powders such as hollow microspheres and especially microspheres formed from a terpolymer of vinylidene chloride, of acrylonitrile and of methacrylate and sold under the name Expancel by the company Kemanord Plast under the references 551 DE 12 (particle size of about 12 μm and density of 40 kg/m3) , 551 DE 20 (particle size of about 30 μm and a density of 65 kg/m3) and 551 DE 50 (particle size of about 40 μm) , or the microspheres sold under the name Micropearl F 80 ED by the company Matsumoto; powders of natural organic materials such as starch powders, especially of corn starch, wheat starch or rice starch, which may or may not be crosslinked, such as the starch powder crosslinked with octenylsuccinate anhydride, sold under the name Dry-Flo by the company National Starch; silicone resin microbeads such as those sold under the name Tospearl by the company Toshiba Silicone, especially Tospearl 240; amino acid powders such as the lauroyllysine powder sold under the name Amihope LL-Il by the company Ajinomoto; particles of wax microdispersion, which preferably have mean sizes of less than 1 μm and especially ranging from 0.02 μm to 1 μm, and which consist essentially of a wax or a mixture of waxes, such as the products sold under the name Aquacer by the company Byk Cera, and especially: Aquacer 520 (mixture of synthetic and natural waxes) , Aquacer 514 or 513 (polyethylene wax) , Aquacer 511 (polymer wax) , or such as the products sold under the name Jonwax 120 by the company Johnson Polymer (mixture of polyethylene wax and paraffin wax) and under the name Ceraflour 961 by the company Byk Cera (micronized modified polyethylene wax) ; and mixtures thereof. The organic powdai (s)—may be present,
£O*3ύT I O 2"I Cl flip j- Q j lxi QiI d IU IU uill L
The cosmetic composition according to the invention may also comprise cosmetic adjuvants chosen from waxes, softeners, antioxidants, opacifiers, stabilizers, moisturizers, vitamins, fragrances, bactericides, preserving agents, polymers, fragrances, thickeners, propellants or any other ingredient usually used in cosmetics for this type of application. Needless to say, a person skilled in the art will take care to select this or these optional additional compound (s) such that the advantageous properties intrinsically associated with the cosmetic composition in accordance with the invention are not, or are not substantially, adversely affected by the envisaged addition (s).
The waxes may be chosen from animal, fossil, plant, mineral and synthetic waxes. Mention may be made especially of beeswax, carnauba wax, candelilla wax, sugar cane wax, Japan wax, ozokerites, montan wax, microcrystalline waxes, paraffins and silicone waxes and resins. The thickeners, which are preferably nonionic, may be chosen from modified or unmodified guar gums and celluloses, such as hydroxypropyl guar gum or cetylhydroxyethylcellulose, silicas, for instance Bentone Gel MIO sold by the company NL Industries, or Veegum Ultra sold by the company Polyplastic.
The amounts of these various constituents that may be present in the cosmetic composition according to the invention are those conventionally used in deodorant compositions.
The compositions according to the invention may also contain one or more other agents for structuring or gelling the water-immiscible organic liquid phase of the composition, such as linear solid fatty alcohols and/or waxes; fatty acids or salts thereof (stearic acid, sodium stearate or 12-hydroxy- stearic acid) ; dibenzylidene alditols (DBS) ; lanosterol, N-acylamino acid derivatives; di- or tricarboxylic acid derivatives, for instance alkyl- N, N1 -dialkylsuccin-amides (i.e.: dodecyl-N,N' - dibutylsuccinamide) ; elastomeric polyorganosiloxanes such as those described in patent application WO 97/44010. The composition according to the invention may also be pressurized and may be packaged in an aerosol device.
The propellants generally used in products of this type, which are well known to those skilled in the art, are, for example, dimethyl ether (DME); volatile hydrocarbons such as n-butane, propane or isobutane, and mixtures thereof, optionally with at least one chlorohydrocarbon and/or fluorohydrocarbon; among the latter, mention may be made of the compounds sold by the company Dupont de Nemours under the names Freon® and Dymel®, and in particular monofluorotrichloro- methane, difluorodichloromethane, tetrafluorodichloro- ethane and 1, 1-difluoroethane sold especially under the trade name Dymel 152 A by the company Dupont. Carbon dioxide, nitrous oxide, nitrogen or compressed air may also be used as propellant.
The composition containing the deodorant active agent (s) and the propellant (s) may be in the same compartment or in different compartments in the aerosol container. According to the invention, the concentration of propellant generally ranges from 5% to 95% by pressurized weight and more preferably from 50% to 85% by weight relative to the total weight of the pressurized composition.
The distribution means, which forms a part of the aerosol device, generally consists of a distribution valve controlled by a distribution head, itself comprising a nozzle via which the aerosol composition is vaporized. The container containing the pressurized composition may be opaque or transparent. It may be made of glass, of polymeric material or of metal, optionally coated with a coat of protective varnish.
A subject of the present invention is also a cosmetic process for treating human underarm odours, which consists in applying to the underarm area an effective amount of a composition as defined above.
The examples that follow serve to illustrate the present invention. The amounts used in the compositions are expressed as weight percentages. Examples I/ Deodorant activity:
1) Test of in vitro efficacy
Underarm sweat is collected in a sauna from 6 volunteers, the samples of individual sweat, stored in ice for a few hours, are then virtually odourless. They are then mixed together and divided into 1 ml aliquots. The active agents are added to these aliquots, which are then incubated in an oven at 37°C. After 18 and 24 hours of incubation, a panel of experts evaluates the intensity of the odour compared with a control sample: 1 ml of sweat incubated without addition of active agent.
The intensity is evaluated on a scale from 0 (no odour) to 4 (very strong odour) . The results are expressed as a percentage of variation of the intensity of the odour compared with this control sweat sample (mean of the percentages of variation at T 18 h and T 24 h) .
? = (odour intensity of the control sample - odour intensity of the sample with active agent) * 100 odour intensity of the control sample
Figure imgf000021_0001
2) Test of in vivo efficacy
A sensory test is performed on a panel of 20 volunteers. The composition is applied in a single application to each volunteer against the untreated armpit in a quantity of 1.2 ± 0.05 g vaporized 15 cm from the armpit. The deodorant is applied after wiping the armpit.- The control armpit is also wiped, but does not receive any treatment. A panel of 5 experts
(5 individuals) evaluates on the volunteers' underarms:
(1) the intensity of the perspiration odour 8 hours after application, and gives a grade from 1 to 9
(1: imperceptible perspiration odour, and 9: extremely strong odour)
(2) the intensity of the unpleasantness or the hedonic value, 8 and 24 hours after application, and gives a grade from 1 to 9 (1: extremely unpleasant odour, and
9: extremely pleasant) .
Test formula: alcoholic aerosol
Figure imgf000022_0001
Procedure
The lipophilic 5-n-octanoylsalicylic derivative is dissolved in the alcohol. The propellant is then introduced in a standard manner.
The results obtained are summarized in the following table:
Figure imgf000022_0002
24 hours after application, it is observed that the deodorant of the invention based on 5-n-octanoylsalicylic allows the intensity of the perspiration odour and also the unpleasantness thereby caused to be reduced very significantly. 11/ Antibacterial activity: demonstration of the bactericidal activity of a composition against the microorganisms involved in underarm odour
The test described here allows a quantitative determination of the bactericidal activity of a composition on microorganisms under optimum growth conditions, i.e. microorganisms of the type Corynebacterium xerosis (Institut Pasteur collection No. 5216) and Brevibacterium me brellneri (Institut Pasteur collection No. 104342) cultured on a gradient of tryptocasein soybean agar.
On the day before the test, 32 g of tryptocasein soybean broth are placed in a pillbottle and incubated at 35°C. On the day of the test, 4 g of the test composition are added and the mixture is homogenized with a Vortex blender.
A growth control without product is prepared under the same conditions in order to check that the microorganisms are under favourable growth conditions throughout the test.
For the preparation of the inoculum, five days before the start of the test, the two bacterial strains are subcultured on suitable medium. They are incubated for 5 days at 35°C. On the day of the test, the gradient is washed with about 9 ml of diluent. The suspension obtained has a titre of
108 microorganisms/ml (counting is performed) . 4 ml of inoculum are introduced into the pillbottle, which corresponds to a proportion of 107 bacteria per gram of preparation. The pillbottle is placed in an incubator- stirrer (35°C - 200 rpm) .
After each contact time (2, 4, 6 and 24 hours) , the contents of the pillbottle are homogenized using a Vortex blender. Tenfold dilutions are performed. The contents are placed on the surface of agar Petri dishes (Eugon LT 100 medium) . The Petri dishes are incubated for 6 to 7 days in an oven at 35°C.
The colonies on the dishes containing more than 20 and less than 200 colonies are counted.
As regards the evaluation as active agent, the results are expressed, for each microorganism tested, as the Log number of reduction after 24 hours relative to the placebo: identical results: none,
1 Log of reduction: poor,
2 Log of reduction: average, 3 Log of reduction: good,
≥ 4 Log of reduction: excellent.
Test formulation: deodorant gel
Figure imgf000024_0001
Figure imgf000025_0001
Results
Figure imgf000025_0002
5-n-Octanoylsalicylic acid has little bactericidal activity on the strains C. xerosis and
B. me brellneri. This salicylic acid derivative is much less bactericidal than Triclosan at a concentration 6 times higher. Example 3: Soap stick:
Figure imgf000025_0003
Figure imgf000026_0001
Procedure :
The stick is prepared according to a standard process for manufacturing a deodorant soap stick. The active agent is dissolved in the water-glycol phase. The stick obtained is uniform and transparent.

Claims

1. Use of at least one lipophilic salicylic acid derivative of formula (I) below, or a salt thereof derived from a mineral base:
Figure imgf000027_0001
in which:
- the radical R denotes a linear, branched or cyclic, saturated aliphatic chain containing from 2 to 22 carbon atoms; an unsaturated chain containing from 2 to 22 carbon atoms containing one or more double bonds that may be conjugated; an aromatic nucleus linked to the carbonyl radical directly or via saturated or . unsaturated aliphatic chains containing from 2. to 7 carbon atoms; the said groups possibly being substituted with one or more substituents, which may be identical or different, chosen from (a) halogen atoms, (b) a trifluoromethyl group, (c) hydroxyl groups in free form or esterified with an acid containing from 1 to 6 carbon atoms, or (d) a carboxyl function in free form or esterified with a lower alcohol containing from 1 to 6 carbon atoms;
- R' is a hydroxyl group. or ester group of formula: —0-C-R1 Il O in which Ri denotes a linear or branched, saturated or unsaturated aliphatic chain containing from 1 to 18 carbon atoms; as deodorant agent in a deodorant cosmetic composition not containing antiperspirant agent.
2. Use according to Claim 1, in which the compound of formula (I) is chosen from those for which the radical R denotes a linear, branched or cyclic, saturated aliphatic chain containing from 3 to 11 carbon atoms; an unsaturated chain containing from 3 to 17 carbon atoms comprising one or more conjugated or unconjugated double bonds; the said hydrocarbon chains possibly being substituted with one or more substituents, which may be identical or different, chosen from (a) halogen atoms, (b) a trifluoromethyl group, (c) hydroxyl groups in free form or esterified with an acid containing from 1 to 6 carbon atoms, or (d) a carboxyl function in free form or esterified with a lower alcohol containing from 1 to 6 carbon atoms; - R' is a hydroxyl group or ester group of formula:
—O-C-Ri Il O in which Ri denotes a -0- (C=O) - (CH2) n-CH3 radical in which n is a number ranging from 0 to 14; and also salts thereof obtained by salification with a mineral base.
3. Use according to Claim 1 or 2, in which the compound of formula (I) is chosen from those for which the radical R is a C3-C11 alkyl group and R' denotes hydroxyl .
4. Use according to any one of Claims 1 to
3, in which the compound of formula (I) is chosen from those for which R represents a chain derived from linoleic acid, linolenic acid or oleic acid.
5. Use according to any one of Claims 1 to 4, in which the compound of formula (I) is chosen from those for which the radical R denotes a C3-Cu alkyl group bearing a carboxyl function in free form or esterified with a lower alcohol containing from 1 to 6 carbon atoms and R' denotes hydroxyl.
6. Use according to any one of the preceding claims, in which the compound of formula (I) is chosen from 5-n-octanoylsalicylic acid (or capryloylsalicylic acid) ; 5-n-decanoylsalicylic acid; 5-n-dodecanoyl- salicylic acid; 5-n-heptyloxysalicylic acid, and the salts thereof derived from a mineral base.
7. Use according to Claim 6, in which the compound of formula (I) is 5-n-octanoylsalicylic acid (or capryloylsalicylic acid) and the salts thereof derived from a mineral base.
8. Use according to any one of the preceding claims, in which the salts of the lipophilic salicylic acid derivatives of formula (I) are obtained by salification with a mineral base chosen from alkali metal and alkaline-earth metal hydroxides.
9. Use according to any one of the preceding claims, in which the concentration of salicylic compound of formula (I) ranges from 0.001% to 20%, more preferentially from 0.01% to 15% and even more preferentially from 0.05% to 5% by weight relative to the total weight of the composition.
10. Cosmetic process for treating human perspiration and human body odour, in particular underarm perspiration and underarm odour, which consists in applying a deodorant composition comprising at least one lipophilic salicylic acid derivative of formula (I) , or a salt thereof derived from a mineral base, as defined according to any one of the preceding claims, and not containing antiperspirant active agent.
PCT/EP2006/003302 2005-04-19 2006-03-15 Use op a lipophilic salicylic acid derivative as a deodorant active agent, process for treating body odour WO2007031117A1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR0550989 2005-04-19
FR0550989A FR2884416B1 (en) 2005-04-19 2005-04-19 USE AS DEODORANT ACTIVE OF A LIPOPHILIC DERIVATIVE OF SALICYLIC ACID IN A DEODORANT COMPOSITION CONTAINING NO ANTITRANSPIRANT AGENT; METHOD OF TREATING BODY ODORS
US67586405P 2005-04-29 2005-04-29
US60/675,864 2005-04-29

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3012960A1 (en) * 2013-11-13 2015-05-15 Oreal USE AS A DEODORANT AGENT OF A SALICYLIC ACID SALICY DERIVATIVE, ALONE OR IN MIXING

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2581542A1 (en) * 1985-05-07 1986-11-14 Oreal TOPICAL COMPOSITIONS FOR THE TREATMENT OF SKIN BASED ON SALICYLIC ACID DERIVATIVES
EP0378936A2 (en) * 1988-12-16 1990-07-25 L'oreal Use of salicylic-acid derivatives in the treatment of aging of the skin
EP1428520A2 (en) * 2002-12-10 2004-06-16 Henkel Kommanditgesellschaft auf Aktien Lipase inhibitors in deodorants and antiperspirants
WO2004073745A1 (en) * 2003-02-19 2004-09-02 L'oréal Salicylic acid derivative as efficacy enhancer and method
EP1486199A1 (en) * 2003-06-02 2004-12-15 L'oreal Alcoholic aerosol deodorant composition containing zinc salicylate or a derivative thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2581542A1 (en) * 1985-05-07 1986-11-14 Oreal TOPICAL COMPOSITIONS FOR THE TREATMENT OF SKIN BASED ON SALICYLIC ACID DERIVATIVES
EP0378936A2 (en) * 1988-12-16 1990-07-25 L'oreal Use of salicylic-acid derivatives in the treatment of aging of the skin
EP1428520A2 (en) * 2002-12-10 2004-06-16 Henkel Kommanditgesellschaft auf Aktien Lipase inhibitors in deodorants and antiperspirants
WO2004073745A1 (en) * 2003-02-19 2004-09-02 L'oréal Salicylic acid derivative as efficacy enhancer and method
EP1486199A1 (en) * 2003-06-02 2004-12-15 L'oreal Alcoholic aerosol deodorant composition containing zinc salicylate or a derivative thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3012960A1 (en) * 2013-11-13 2015-05-15 Oreal USE AS A DEODORANT AGENT OF A SALICYLIC ACID SALICY DERIVATIVE, ALONE OR IN MIXING
WO2015071374A1 (en) 2013-11-13 2015-05-21 L'oreal Use as a deodorant agent of a salified salicylic acid derivative, alone or in a mixture

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