WO2003002072A1 - Compositions containing a hydroxydiphenyl ether derivative inhibiting body odours - Google Patents

Compositions containing a hydroxydiphenyl ether derivative inhibiting body odours Download PDF

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Publication number
WO2003002072A1
WO2003002072A1 PCT/FR2002/001788 FR0201788W WO03002072A1 WO 2003002072 A1 WO2003002072 A1 WO 2003002072A1 FR 0201788 W FR0201788 W FR 0201788W WO 03002072 A1 WO03002072 A1 WO 03002072A1
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WO
WIPO (PCT)
Prior art keywords
hydroxy
diphenyl ether
aluminum
composition
methyl
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Application number
PCT/FR2002/001788
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French (fr)
Inventor
Serge Forestier
Christophe Courbiere
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L'oréal
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Publication date
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Publication of WO2003002072A1 publication Critical patent/WO2003002072A1/en

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00Anti-perspirants or body deodorants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/046Aerosols; Foams
    • 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
    • A61K8/34Alcohols
    • A61K8/347Phenols

Definitions

  • the present invention relates to an aerosol device consisting of a container comprising an aerosol composition consisting, on the one hand, of a liquid phase (a) (or juice) comprising at least one derivative of hydroxydiphenyl ether and (b) of at least at least one particular propellant and by a means of distributing said aerosol composition as well as to the process for treating human body odors and in particular axillary using this device.
  • 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.
  • Triclosan (2,4,4'-trichloro-2'-hydroxydiphenylether).
  • the present invention thus firstly relates to an aerosol device consisting of a container comprising an aerosol composition and a means of dispensing said aerosol composition, the latter comprising a liquid phase (or juice) containing: a) at least one derivative of 'hydroxydiphenyl ethers of formula (1):
  • Z and Z ' identical or different, denote H, a linear or branched C ⁇ -C 30 hydrocarbon radical, cyclic or acyclic, saturated or unsaturated, 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
  • At least one propellant selected from dimethyl ether, linear or branched alkanes containing from 2 to 6 carbon atoms or their mixtures.
  • the concentration of compound (s) of formula (1) preferably varies from 0.001 to 20%, more preferably from 0.01 to 15% and even more preferably from 0.1 to 10% by weight per relative to the total weight of the composition.
  • the propellant is chosen from dimethyl ether, volatile hydrocarbons such as n-butane, propane, isobutane and their mixtures.
  • composition containing the compound (s) of formula (1) and the propellant (s) may be in the same compartment or in different compartments in the aerosol container.
  • the concentration of propellant (s) generally varies from 5 to 90% by weight pressurized and more preferably from 15 to 70% by weight relative to the total weight of the pressurized composition.
  • composition according to the invention may also contain deodorant active agents or antiperspirant active agents.
  • deodorant active agents there may be mentioned for example, zinc pyrrolidone carboxylate (more commonly called zinc pidolate), zinc sulfate, zinc chloride, zinc lactate, zinc gluconate and zinc phenoisulfonate, 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).
  • zinc pyrrolidone carboxylate more commonly called zinc pidolate
  • zinc sulfate zinc chloride
  • zinc lactate zinc gluconate
  • zinc phenoisulfonate 2,4,4'-trichloro-2'-
  • antiperspirant active agents there may be mentioned for example aluminum hydrochloride, aluminum chlorohydrex, aluminum chlorohydrex PEG, aluminum chlorohydrex PG, aluminum dichlorohydrate, aluminum dichlorohydrex PEG, aluminum dichlorohydrex PG, l 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 US Pat. No. 3,792,068.
  • 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.
  • glycine aluminum zirconium octachlorohydrex GLY, aluminum zirconium pentachlorohydrex GLY, aluminum zirconium tetrachlorohydrate GLY and aluminum zirconium trichlorohydrate-GLY.
  • deodorant or antiperspirant active agents may be present in the composition according to the invention in an amount of approximately 0.001 to 20% by weight relative to the total composition, and 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.
  • a cosmetically acceptable vehicle which may in particular be essentially aqueous, or contain organic solvents and in particular CrC monoalcohols, preferably of 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, oil-in-water emulsion, 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, basifying or acidifying agents, perfumes, dyes, pigments, thickening agents, or any other ingredient usually used in cosmetics for this type of application .
  • 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, basifying or acidifying agents, perfumes, dyes, pigments, thickening agents, or any other ingredient usually used in cosmetics for this type of application .
  • the surfactants are preferably chosen from anionic, amphoteric or nonionic surfactants.
  • the fatty substances can consist of an oil or a wax or a mixture thereof, 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, isoprppyl adipate, isopropyl palmitate, octyl palmitate, C12-C15 fatty alcohol benzoates (Finsolv TN from FINETEX), myristic alcohol polyoxypropylenated to 3 moles of propylene oxide (WITCONOL APM from WITCO), triglycerides of fatty acids in C ⁇ -C-js such as caprylic / capric acid triglycer
  • 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 beeswaxes, Camauba, Candellila, sugar cane, Japanese waxes, ozokerites, Montan 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.
  • 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.
  • polyalkylsiloxanes in particular linear polyalkylsiloxanes such as, for example, the linear polydimethylsiloxanes, or dimethicones, sold by the company Dow Corning under the name of "Dow Corning 200 Fluid”
  • polyalkylarylsiloxanes 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.
  • nonvolatile emollients useful in the present invention include for example: hydrocarbon-based derivatives, mineral oils, fatty alcohols, alcohol esters of C 3 -C ⁇ 8 with acids C 3 -C ⁇ 8 , the esters of benzoic acid with alcohols in C ⁇ 2 -C ⁇ 8 and their mixtures, polyols in C 2 -C 6 preferably chosen from glycerol, propylene glycol or sorbitol, polymers of polalkylene glycol.
  • the cosmetic composition according to the invention can thus be in the form of a lotion, cream or fluid gel distributed in aerosol spray, and in this regard contain the ingredients generally used in this type of product and well known to those skilled in the art. 'art.
  • the dispensing means which forms part of the aerosol device, generally consists of a dispensing valve controlled by a dispensing head, itself comprising a nozzle by which the aerosol composition is vaporized.
  • the container containing the pressurized composition can be opaque or transparent.
  • the following aerosol device is produced in accordance with the invention by introducing the following juice and the propellants into an aerosol container provided with conventional dispensing means.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
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  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Cosmetics (AREA)

Abstract

The invention concerns an aerosol device consisting of a container comprising a aerosol composition consisting of a liquid phase (a) (or liquor) comprising at least a hydroxydiphenyl ether derivative and (b) at least a particular propellant and of means for dispensing said aerosol composition as well as the method for treating human body odours and in particular axillary odours with said device.

Description

COMPOSITIONS CONTENANT UN DERIVE D'HYDROXYDIPHENYL ETHER INHIBANT LE DEVELOPPEMENT DES ODEURS CORPORELLES COMPOSITIONS CONTAINING A HYDROXYDIPHENYL ETHER DERIVATIVE INHIBITING THE DEVELOPMENT OF BODY ODORS
La présente invention a trait à un dispositif aérosol constitué par un récipient comprenant une composition aérosol constituée, d'une part par une phase liquide (a)( ou jus) comprenant au moins un dérivé d'hydroxydiphényl éther et (b) d'au moins un agent propulseur particulier et par un moyen de distribution de la dite composition aérosol ainsi qu'au procédé de traitement des odeurs corporelles humaines et notamment axillaires à l'aide de ce dispositif.The present invention relates to an aerosol device consisting of a container comprising an aerosol composition consisting, on the one hand, of a liquid phase (a) (or juice) comprising at least one derivative of hydroxydiphenyl ether and (b) of at least at least one particular propellant and by a means of distributing said aerosol composition as well as to the process for treating human body odors and in particular axillary using this device.
Dans le domaine cosmétique, il est bien connu d'utiliser, en application topique, des produits déodorants contenant des substances actives, de type antitranspirant ou de type bactéricide, pour diminuer, voire supprimer, les odeurs axillaires généralement désagréables.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.
Les substances antitranspirantes ont pour effet de limiter le flux sudoral. Elles sont généralement constituées de sels d'aluminium qui, d'une part, sont irritants pour la peau et qui, d'autre part, diminuent le flux sudoral en modifiant la physiologie cutanée, ce qui n'est pas satisfaisant.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.
Les substances bactéricides inhibent le développement de la flore cutanée responsable des odeurs axillaires.Bactericidal substances inhibit the development of the skin flora responsible for axillary odors.
Parmi les produits bactéricides, le plus couramment employé est le Triclosan (2,4,4'-trichloro-2'-hydroxydiphényléther).Among the bactericidal products, the most commonly used is Triclosan (2,4,4'-trichloro-2'-hydroxydiphenylether).
Dans le but d'obtenir une efficacité à long terme, on recherche de nouveaux produits exerçant une action déodorante, c'est-à-dire des produits qui soient capables de modifier, de réduire et/ou d'ôter ou de prévenir le développement des odeurs corporelles (cette définition est donnée dans l'ouvrage « Cosmetic Science and Technology Séries » - 1988 / Volume 7 chap.10 - lllc). Dans la demande de brevet EP1053989, on a cité l'utilisation en cosmétique dé dérivés d'hydroxydiphényl éthers comme actifs antimicrobiens en particulier pour désodoriser la peau, les muqueuses, les cheveux, les matériaux divers comme le papier, la peinture. Ces dérivés peuvent être utilisés sous différentes formes galeniques telles que des solutions, des lotions, des emulsions qui peuvent être délivrées par exemple sous forme de compositions à pulvériser. La présentation sous forme de dispositif aérosol mis sous pression à l'aide d'un agent propulseur est particulièrement appréciée par les consommateurs. La nature de l'agent propulseur joue un rôle capital dans la stabilité de la composition et la qualité de la pulvérisation et par conséquent dans l'efficacité du produit.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 - lllc). In patent application EP1053989, use has been made in cosmetics of derivatives of hydroxydiphenyl ethers as antimicrobial active agents in particular for deodorizing the skin, mucous membranes, hair, various materials such as paper, paint. These derivatives can be used in different galenical forms such as solutions, lotions, emulsions which can be delivered, for example, in the form of spray compositions. The presentation in the form of an aerosol device pressurized with a propellant is particularly appreciated by consumers. The nature of the propellant plays a crucial role in the stability of the composition and the quality of the spray and therefore in the effectiveness of the product.
Après de nombreuses recherches menées sur la question, la Demanderesse a maintenant découvert, de façon inattendue et surprenante, que des dispositifs aérosols associant des compositions contenant des dérivés d'hydroxydiphényl éthers avec des agents propulseurs particuliers présentaient la propriété de prévenir le développement des odeurs de sueur corporelle, sans les inconvénients liés à l'utilisation des autres agents propulseurs .After numerous researches carried out on the question, the Applicant has now discovered, unexpectedly and surprisingly, that aerosol devices associating compositions containing derivatives of hydroxydiphenyl ethers with particular propellants had the property of preventing the development of odors. body sweat, without the drawbacks of using other propellants.
Cette découverte est à la base de la présente invention.This discovery is the basis of the present invention.
La présente invention a ainsi pour premier objet un dispositif aérosol constitué par un récipient comportant une composition aérosol et un moyen de distribution de la dite composition aérosol,celle-ci comprenant une phase liquide (ou jus) contenant : a) au moins un dérivé d'hydroxydiphényl éthers de formule (1) :The present invention thus firstly relates to an aerosol device consisting of a container comprising an aerosol composition and a means of dispensing said aerosol composition, the latter comprising a liquid phase (or juice) containing: a) at least one derivative of 'hydroxydiphenyl ethers of formula (1):
Figure imgf000003_0001
Figure imgf000003_0001
dans laquelle R1 , R2, R3 et R4, identiques ou différentes, désignent Z, OZ, COZ, COOZ, CONZZ', aryle en C6-C3o ou aralkyle en C7-C40 ou alkyaryle en C7-C40 éventuellement substitués par un ou plusieurs groupements choisis parmi OH,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 40 alkylaryl or C 7 -C 40 optionally substituted by one or more groups chosen from OH,
NH2, halogène, carboxy, ou alcoxy C1-C30 carbonyle ;NH 2 , halogen, carboxy, or C1-C30 carbonyl alkoxy;
Z et Z', identiques ou différentes, désignent H, un radical hydrocarboné Cι-C30 linéaire ou ramifié, cyclique ou acyclique, saturé ou insaturé, interrompu ou non par un plusieurs heteroatomes ou groupements carbonyles, substitué ou non par un ou plusieurs groupements choisis parmi OH, NH2, halogène, carboxy ou alcoxyZ and Z ', identical or different, denote H, a linear or branched Cι-C 30 hydrocarbon radical, cyclic or acyclic, saturated or unsaturated, 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
C-ι-C30 carbonyle ; b) au moins un agent propulseur sélectionné parmi le diméthyléther, les alcanes linéaires ou ramifiés contenant de 2 à 6 atomes de carbone ou leurs mélanges.C-ι-C 30 carbonyl; b) at least one propellant selected from dimethyl ether, linear or branched alkanes containing from 2 to 6 carbon atoms or their mixtures.
Parmi les composés de formule (1) utilisables selon la présente invention on préfère :Among the compounds of formula (1) which can be used according to the present invention, preference is given to:
- Le 2,4'-dihydroxy diphényl éther- 2,4'-dihydroxy diphenyl ether
- Le 2-hydroxy 2'-éthyl diphényl éther- 2-hydroxy 2'-ethyl diphenyl ether
- Le 2-hydroxy 2'-isopropyl diphényl éther- 2-hydroxy 2'-isopropyl diphenyl ether
- Le 2-hydroxy 2'-méthyl diphényl éther- 2-hydroxy 2'-methyl diphenyl ether
- Le 2-hydroxy 2'-sec.butyl diphényl éther- 2-hydroxy 2'-sec.butyl diphenyl ether
- Le 2-hydroxy 2'-tert.butyl diphényl éther- 2-hydroxy 2'-tert.butyl diphenyl ether
- Le 2-hydroxy 3-butanoyl diphényl éther- 2-hydroxy 3-butanoyl diphenyl ether
- Le 2-hydroxy 3-propanoyl diphényl éther- 2-hydroxy 3-propanoyl diphenyl ether
- Le 2-hydroxy 4-formyl diphényl éther- 2-hydroxy 4-formyl diphenyl ether
- Le 2-hydroxy 4'-méthyl 5-formyl diphényl éther- 2-hydroxy 4'-methyl 5-formyl diphenyl ether
- Le 2-hydroxy 5-butanoyl diphényl éther- 2-hydroxy 5-butanoyl diphenyl ether
- Le 2-hydroxy 5-formyl diphényl éther- 2-hydroxy 5-formyl diphenyl ether
- Le 2-hydroxy diphényl éther- 2-hydroxy diphenyl ether
- Le 3-hydroxy 2'-méthyl diphényl éther- 3-hydroxy 2'-methyl diphenyl ether
- Le 3-hydroxy 2'-sec.butyl diphényl éther- 3-hydroxy 2'-sec.butyl diphenyl ether
- Le 3-hydroxy 2'-méthyl 4-n-propyl diphényl éther- 3-hydroxy 2'-methyl 4-n-propyl diphenyl ether
- Le 3-hydroxy 3'-méthyl diphényl éther- 3-hydroxy 3'-methyl diphenyl ether
- Le 3-hydroxy 3'-méthyl 4-n-propyl diphényl éther- 3-hydroxy 3'-methyl 4-n-propyl diphenyl ether
- Le 3-hydroxy 4-(1 -hydroxy 2-méthylpropyl) diphényl éther- 3-hydroxy 4- (1-hydroxy 2-methylpropyl) diphenyl ether
- Le 3-hydroxy 4-butanoyl diphényl éther - Le 3-hydroxy 4-butyl diphényl éther- 3-hydroxy 4-butanoyl diphenyl ether - 3-hydroxy 4-butyl diphenyl ether
- Le 3-hydroxy 4-diméthylpropyl diphényl éther- 3-hydroxy 4-dimethylpropyl diphenyl ether
- Le 3-hydroxy 4-diméthylpropyl 3'-méthyl diphényl éther- 3-hydroxy 4-dimethylpropyl 3'-methyl diphenyl ether
- Le 3-hydroxy 4-hexyl diphényl éther- 3-hydroxy 4-hexyl diphenyl ether
- Le 3-hydroxy 4-hexanoyl diphényl éther- 3-hydroxy 4-hexanoyl diphenyl ether
- Le 3-hydroxy 4-dodécyl diphényl éther- 3-hydroxy 4-dodecyl diphenyl ether
- Le 3-hydroxy 4-isobutanoyl diphényl éther- 3-hydroxy 4-isobutanoyl diphenyl ether
- Le 3-hydroxy 4-isobutyl diphényl éther- 3-hydroxy 4-isobutyl diphenyl ether
- Le 3-hydroxy 4-isopentanoyl diphényl éther- 3-hydroxy 4-isopentanoyl diphenyl ether
- Le 3-hydroxy 4-isopropyl diphényl éther- 3-hydroxy 4-isopropyl diphenyl ether
- Le 3-hydroxy 4'-isopropyl diphényl éther- 3-hydroxy 4'-isopropyl diphenyl ether
- Le 3-hydroxy 4-n-butyl diphényl éther- 3-hydroxy 4-n-butyl diphenyl ether
- Le 3-hydroxy 4-n-butyl diphényl éther- 3-hydroxy 4-n-butyl diphenyl ether
- Le 3-hydroxy 4-n-pentyl diphényl éther- 3-hydroxy 4-n-pentyl diphenyl ether
- Le 3-hydroxy 4-n-propyl diphényl éther- 3-hydroxy 4-n-propyl diphenyl ether
- Le 3-hydroxy 4-pentanoyl diphényl éther- 3-hydroxy 4-pentanoyl diphenyl ether
- Le 3-hydroxy 4-pentyl diphényl éther- 3-hydroxy 4-pentyl diphenyl ether
- Le 3-hydroxy 4-phenyléthyl diphényl éther- 3-hydroxy 4-phenylethyl diphenyl ether
- Le 3-hydroxy 2'-méthyl 4-phenyléthyl diphényl éther .- 3-hydroxy 2'-methyl 4-phenylethyl diphenyl ether.
- Le 3-hydroxy 3'-méthyl 4-phenyléthyl diphényl éther- 3-hydroxy 3'-methyl 4-phenylethyl diphenyl ether
- Le 3-hydroxy 4-propanoyl diphényl éther- 3-hydroxy 4-propanoyl diphenyl ether
- Le 3-hydroxy diphényl éther- 3-hydroxy diphenyl ether
- Le 3,4'-dihydroxy diphényl éther- 3,4'-dihydroxy diphenyl ether
- Le 4,4'-dihydroxy diphényl éther- 4,4'-dihydroxy diphenyl ether
- Le 4-hydroxy 2'- méthyl 5'-isopropyl diphényl éther- 4-hydroxy 2'-methyl 5'-isopropyl diphenyl ether
- Lé 4-hydroxy 2'- tert.butyl 5'-méthyl diphényl éther- Lé 4-hydroxy 2'- tert.butyl 5'-methyl diphenyl ether
- Le 4-hydroxy 2',5'-diméthyl diphényl éther- 4-hydroxy 2 ', 5'-dimethyl diphenyl ether
- Le 4-hydroxy 2'-cyclohexyl 5'-méthyl diphényl éther- 4-hydroxy 2'-cyclohexyl 5'-methyl diphenyl ether
- Le 4-hydroxy 2'-isopropyl 4'-éthyl diphényl éther- 4-hydroxy 2'-isopropyl 4'-ethyl diphenyl ether
- Le 4-hydroxy 2'-isopropyl 4'-propyl diphényl éther- 4-hydroxy 2'-isopropyl 4'-propyl diphenyl ether
- Le 4-hydroxy 2'-isopropyl 5'-méthyl diphényl éther- 4-hydroxy 2'-isopropyl 5'-methyl diphenyl ether
- Le 4-hydroxy 2'-isopropyl diphényl éther- 4-hydroxy 2'-isopropyl diphenyl ether
- Le 4-hydroxy 2'-isopropyl 4'-phényléthyl diphényl éther - Le 4-hydroxy 3-(3-méthylbutyl) 4'-(3-méthylbutyl) diphényl éther- 4-hydroxy 2'-isopropyl 4'-phenylethyl diphenyl ether - 4-hydroxy 3- (3-methylbutyl) 4 '- (3-methylbutyl) diphenyl ether
- Le 4-hydroxy 4'-diméthylpropyl diphényl éther- 4-hydroxy 4'-dimethylpropyl diphenyl ether
- Le 4-hydroxy 4'-éthyl diphényl éther- 4-hydroxy 4'-ethyl diphenyl ether
- Le 4-hydroxy 4'-nonyl diphényl éther- 4-hydroxy 4'-nonyl diphenyl ether
- Le 4-hydroxy 4'-phényléthyl diphényl éther- 4-hydroxy 4'-phenylethyl diphenyl ether
- Le 4-hydroxy 4'-propyl diphényl éther- 4-hydroxy 4'-propyl diphenyl ether
- Le 4-hydroxy 4'-trifluorométhyl diphényl éther- 4-hydroxy 4'-trifluoromethyl diphenyl ether
- Le 4-hydroxy 4'-propanoyl diphényl éther- 4-hydroxy 4'-propanoyl diphenyl ether
- Le 4-hydroxy diphényl éther- 4-hydroxy diphenyl ether
Encore plus preferentiellement on utilisera le 4,4'-dihydroxydiphényl éther.Even more preferably, 4,4'-dihydroxydiphenyl ether will be used.
Dans les compositions a) de l'invention, la concentration en composé(s) de formule (1) varie de préférence de 0.001 à 20%, plus preferentiellement de 0.01 à 15% et encore plus preferentiellement de 0.1 à 10% en poids par rapport au poids total de la composition.In the compositions a) of the invention, the concentration of compound (s) of formula (1) preferably varies from 0.001 to 20%, more preferably from 0.01 to 15% and even more preferably from 0.1 to 10% by weight per relative to the total weight of the composition.
L'agent propulseur est choisi parmi le diméthyléther, les hydrocarbures volatils tels que le n-butane, le propane, l'isobutane et leurs mélanges.The propellant is chosen from dimethyl ether, volatile hydrocarbons such as n-butane, propane, isobutane and their mixtures.
La composition contenant le ou les composés de formule (1) et le ou les agents propulseurs peuvent se trouver dans le même compartiment ou dans des compartiments différents dans le récipient aérosol.The composition containing the compound (s) of formula (1) and the propellant (s) may be in the same compartment or in different compartments in the aerosol container.
Selon l'invention, la concentration en agent(s) propulseur(s) varie généralement de 5 à 90% en poids pressurisée et plus preferentiellement de 15 à 70% en poids par rapport au poids total de la composition pressurisée.According to the invention, the concentration of propellant (s) generally varies from 5 to 90% by weight pressurized and more preferably from 15 to 70% by weight relative to the total weight of the pressurized composition.
En plus des dérivés d'hydroxydiphényl éthers de formule (1), la composition selon l'invention peut également contenir des actifs déodorants ou des actifs antitranspirants .In addition to the hydroxydiphenyl ether derivatives of formula (1), the composition according to the invention may also contain deodorant active agents or antiperspirant active agents.
Parmi les actifs déodorants selon l'invention on peut citer par exemple, le pyrrolidone carboxylate de zinc (plus communément appelé pidolate de zinc), le sulfate de zinc, le chlorure de zinc, le lactate de zinc, le gluconate de zinc et le phenoisulfonate de zinc, le 2,4,4'-trichloro-2'-hydroxydiphényléther (Triclosan), le 2,4-dichloro-2'-hydroxydiphényléther, le 3',4',5'-trichlorosalicylanilide, la 1-(3',4'- dichlorophenyl)-3-(4'-chlorophenyl)urée (triclocarban) ou le 3,7,11- triméthyldodéca-2,5,10-triénol (Famesol).Among the deodorant active agents according to the invention, there may be mentioned for example, zinc pyrrolidone carboxylate (more commonly called zinc pidolate), zinc sulfate, zinc chloride, zinc lactate, zinc gluconate and zinc phenoisulfonate, 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).
Parmi les actifs antitranspirants on peut citer par exemple le chlorhydrate d'aluminium, l'aluminium chlorohydrex, l'aluminium chlorohydrex PEG, l'aluminium chlorohydrex PG, l'aluminium dichlorohydrate, l'aluminium dichlorohydrex PEG, l'aluminium dichlorohydrex PG, l'aluminium sesquichlorohydrate, l'aluminium sesquichlorohydrex PEG, l'aluminium sesquichlorohydrex PG, l'aluminium sulfate, l'aluminium zirconium octachlorohydrate, l'aluminium zirconium pentachlorohydrate, l'aluminium zirconium tetrachlorohydrate, l'aluminium zirconium trichlorohydrate, les complexes de métaux (comme l'aluminium ou le zirconium) avec un acide aminé et tels que décrits dans le brevet US-3792068. De tels complexes sont généralement connus sous l'appellation ZAG. Les complexes ZAG présentent d'ordinaire un quotient Al/Zr allant d'environ 1 ,67 à 12,5 et un quotient Métal/Cl allant d'environ 0,73 à 1 ,93.Among the antiperspirant active agents there may be mentioned for example aluminum hydrochloride, aluminum chlorohydrex, aluminum chlorohydrex PEG, aluminum chlorohydrex PG, aluminum dichlorohydrate, aluminum dichlorohydrex PEG, aluminum dichlorohydrex PG, l 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 US Pat. No. 3,792,068. 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.
L'amino-acide préféré pour préparer de tels complexes ZAG est la glycine. Parmi ces produits on peut citer l'aluminium zirconium octachlorohydrex GLY, l'aluminium zirconium pentachlorohydrex GLY, l'aluminium zirconium tetrachlorohydrate GLY et l'aluminium zirconium trichlorohydrate-GLY.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.
Ces actifs déodorants ou antitranspirants peuvent être présents dans la composition selon l'invention à raison d'environ 0,001 à 20% en poids par rapport à la composition totale, et de préférence à raison d'environ 0,1 à 10% en poids.These deodorant or antiperspirant active agents may be present in the composition according to the invention in an amount of approximately 0.001 to 20% by weight relative to the total composition, and preferably in an amount of approximately 0.1 to 10% by weight.
La composition cosmétique selon l'invention est formulée classiquement selon la forme de présentation à laquelle elle est destinée.The cosmetic composition according to the invention is conventionally formulated according to the form of presentation for which it is intended.
Elle est plus particulièrement formulée dans un véhicule cosmétiquement acceptable qui peut être notamment essentiellement aqueux, ou contenir des solvants organiques et notamment des monoalcools en CrC , de préférence de l'éthanol pour accélérer l'évaporation du produit, ou du propylène glycol, du dipropylène glycol ou leurs éthers.It is more particularly formulated in a cosmetically acceptable vehicle which may in particular be essentially aqueous, or contain organic solvents and in particular CrC monoalcohols, preferably of ethanol to accelerate the evaporation of the product, or propylene glycol, dipropylene glycol or their ethers.
La composition cosmétique selon l'invention peut également être formulée en émulsion eau-dans-huile, huile-dans-eau, ou en émulsion triple eau-dans-huile- dans-eau, (de telles emulsions sont connues et décrites par exemple par C. FOX dans « Cosmetics and Toiletries » - november 1986 - Vol 101 - pages 101-112).The cosmetic composition according to the invention can also be formulated as a water-in-oil, oil-in-water emulsion, 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).
La composition cosmétique selon l'invention peut comprendre en outre des adjuvants cosmétiques choisis parmi les corps gras, les gélifiants, les émollients, les adoucissants, les antioxydants, les opacifiants, les stabilisants, les agents antimousse, les agents hydratants, les vitamines, les parfums, les conservateurs, les tensioactifs, les charges, les séquestrants, les polymères, les agents alcalinisants ou acidifiants, les parfums, les colorants, les pigments, les agents épaississants, ou tout autre ingrédient habituellement utilisé en cosmétique pour ce type d'application.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, basifying or acidifying agents, perfumes, dyes, pigments, thickening agents, or any other ingredient usually used in cosmetics for this type of application .
Bien entendu, l'homme de métier veillera à choisir ce ou ces éventuels composés complémentaires de manière telle que les propriétés avantageuses attachées intrinsèquement à la composition cosmétique conforme à l'invention ne soient pas, ou substantiellement pas, altérées par la ou les adjonctions envisagées.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 not substantially, altered by the addition (s) envisaged. .
Les tensio-actifs sont choisis de préférence parmi les tensio-actifs anioniques, amphotères ou non-ioniques.The surfactants are preferably chosen from anionic, amphoteric or nonionic surfactants.
Les corps gras peuvent être constitués par une huile ou une cire ou leur mélange, la vaseline, la paraffine, la lanoline, la lanoline hydrogénée, la lanoline acétylée ; ils comprennent également les acides gras, les alcools gras tels que l'alcool laurique, cétylique, myristique, stéarique, palmitique, oléique ainsi que le 2- octyldodécanol, les esters d'acides gras tels que le monostéarate de glycérol, le monostéarate de polyéthylèneglycol, le myristate d'isopropyle, l'adipate d'isoprppyle, le palmitate d'isopropyle, le palmitate d'octyle, les benzoates d'alcools gras en C12-C15 (Finsolv TN de FINETEX), l'alcool myristique polyoxypropyléné à 3 moles d'oxyde de propylène (WITCONOL APM de WITCO), les triglycérides d'acides gras en Cρ-C-js tels que les triglycérides d'acide caprylique/caprique.The fatty substances can consist of an oil or a wax or a mixture thereof, 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, isoprppyl adipate, isopropyl palmitate, octyl palmitate, C12-C15 fatty alcohol benzoates (Finsolv TN from FINETEX), myristic alcohol polyoxypropylenated to 3 moles of propylene oxide (WITCONOL APM from WITCO), triglycerides of fatty acids in Cρ-C-js such as caprylic / capric acid triglycerides.
Les huiles sont choisies parmi les huiles animales, végétales, minérales ou de synthèse et notamment l'huile de palme hydrogénée, l'huile de ricin hydrogénée, l'huile de vaseline, l'huiie de paraffine, l'huile de Purcellin (octanoate de stéaryle), les huiles de silicone et les isoparaffines.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.
Les cires sont choisies parmi les cires animales, fossiles, végétales, minérales ou de synthèse. On peut citer notamment les cires d'abeille, les cires de Camauba, de Candellila, de canne à sucre, du Japon, les ozokerites, la cire de Montan, les cires microcristallines, les paraffines, les cires et résines de silicone.The waxes are chosen from animal, fossil, vegetable, mineral or synthetic waxes. Mention may in particular bees beeswaxes, Camauba, Candellila, sugar cane, Japanese waxes, ozokerites, Montan wax, microcrystalline waxes, paraffins, waxes and silicone resins.
Les épaississants, de préférence non ioniques, peuvent être choisis parmi les gommes de guar et celluloses modifiées ou non modifiées telles que la gomme de guar hydroxypropylee, la cetylhydroxyethylcellulose, les silices comme par exemple la Bentone Gel MiO vendue, par la société NL INDUSTRIES ou la Veegum Ultra, vendue par la société POLYPLASTIC.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.
La composition cosmétique peut comprendre des émollients, qui contribuent à une sensation douce, sèche, non-collante à l'application de la composition sur la peau. Ces émollients peuvent être choisis parmi des produits du type silicone volatile, des silicones non-volatiles et d'autres émollients non-volatils.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.
Les silicones volatiles sont définies de façon connue comme des composés volatils à température ambiante. On peut citer parmi ces composés les silicones volatiles cycliques et linéaires du type diméthylsiloxane dont les chaînes comprennent de 3 à 9 résidus silicones. De préférence on choisit les cyclométhicones D4 ou D5.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.
Les silicones non-volatiles sont définies de façon connue comme des composés de pression de vapeur faible à température ambiante. Parmi ces composés sont inclus : les polyalkylsiloxanes, en particulier les polyalkylsiloxanes linéaires comme par exemple les polydiméthylsiloxanes, ou diméthicones, linéaires, commercialisés par la société Dow Corning sous le nom de « Dow Corning 200 Fluid » ; les polyalkylarylsiloxanes comme par exemple les polymethylphenylsiloxanes, commercialisés par la société Dow Corning sous le nom de « Dow Corning 556 Fluid » ; les copolymères polyéther et siloxane, comme par exemple les diméthicone copolyols.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, the linear polydimethylsiloxanes, or dimethicones, sold by the company Dow Corning under the name of "Dow Corning 200 Fluid"; polyalkylarylsiloxanes 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.
Parmi les émollients non-volatils utilisables dans la présente invention, on peut citer par exemple : les dérivés hydrocarbonés, les huiles minérales, les alcools gras, les esters d'alcools en C3-Cι8 avec des acides en C3-Cι8, les esters de l'acide benzoïque avec des alcools en Cι2-Cι8 et leurs mélanges, des polyols en C2-C6 choisis de préférence parmi le glycérol, le propylèneglycol ou le sorbitol, les polymères de polalkylène glycol.Among the nonvolatile 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 , the esters of benzoic acid with alcohols in Cι 2 -Cι 8 and their mixtures, polyols in C 2 -C 6 preferably chosen from glycerol, propylene glycol or sorbitol, polymers of polalkylene glycol.
Les quantités de ces différents constituants pouvant être présents dans la composition cosmétique selon l'invention sont celles classiquement utilisées pour les formes de présentation considérées.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.
La composition cosmétique selon l'invention peut ainsi se présenter sous forme de lotion, de crème ou de gel fluide distribués en spray aérosol, et contenir à cet égard les ingrédients généralement utilisés dans ce type de produits et bien connus de l'homme de l'art.The cosmetic composition according to the invention can thus be in the form of a lotion, cream or fluid gel distributed in aerosol spray, and in this regard contain the ingredients generally used in this type of product and well known to those skilled in the art. 'art.
Le moyen de distribution, qui forme une partie du dispositif aérosol, est généralement constitué par une valve de distribution commandée par une tête de distribution, elle même comprenant une buse par laquelle la composition aérosol est vaporisée.The dispensing means, which forms part of the aerosol device, generally consists of a dispensing valve controlled by a dispensing head, itself comprising a nozzle by which the aerosol composition is vaporized.
Le récipient contenant la composition pressurisée peut être opaque ou transparent.The container containing the pressurized composition can be opaque or transparent.
Il peut être en verre, en matériau polymérique ou en métal, recouvert éventuellement d'une couche de vernis protecteur. Un exemple concret, mais nullement limitatif, illustrant l'invention va maintenant être donné.It can be made of glass, polymeric material or metal, possibly covered with a layer of protective varnish. A concrete, but in no way limiting, example illustrating the invention will now be given.
On réalise le dispositif aérosol suivant conforme à l'invention en introduisant le jus suivant et les propulseurs dans un récipient aérosol munis des moyens de distribution classiquesThe following aerosol device is produced in accordance with the invention by introducing the following juice and the propellants into an aerosol container provided with conventional dispensing means.
JusJuice
4,4'-dihydroxy diphényl éther 2,0g4,4'-dihydroxy diphenyl ether 2.0g
Ethanol qsp 100,0 gEthanol qs 100.0 g
Schéma de pressurisationPressurization scheme
Jus 37%Juice 37%
Diméthyléther 43%Dimethyl ether 43%
Pentane 20% Pentane 20%

Claims

REVENDICATIONS
1. Dispositif aérosol constitué par un récipient comportant une composition aérosol et un moyen de distribution de la dite composition aérosol, celle-ci comprenant une phase liquide (ou jus) contenant : a) au moins un dérivé d'hydroxydiphényl éther de formule (1) :1. Aerosol device consisting of a container comprising an aerosol composition and a means of dispensing said aerosol composition, the latter comprising a liquid phase (or juice) containing: a) at least one hydroxydiphenyl ether derivative of formula (1 ):
Figure imgf000012_0001
dans laquelle R1 , R2, R3 et R4, identiques ou différentes, désignent Z, OZ, COZ, COOZ, CONZZ', aryle en C6-C3ά ou aralkyle en C7-C40 ou alkyaryle en C7-C40 éventuellement substitués par un ou plusieurs groupements choisis parmi OH, NH2, halogène, carboxy, ou alcoxy C1-C30 carbonyle ; Z et Z', identiques ou différentes, désignent H, un radical hydrocarboné C1-C30 linéaire ou ramifié, cyclique ou acyclique, saturé ou insaturé, interrompu ou non par un plusieurs heteroatomes ou groupements carbonyles, substitué ou non par un ou plusieurs groupements choisis parmi OH, NH2, halogène, carboxy ou alcoxy C1-C30 carbonyle ; b) au moins un agent propulseur sélectionné parmi le diméthyléther, les alcanes linéaires ou ramifiés contenant de 2 à 6 atomes de carbone ou leurs mélanges.
Figure imgf000012_0001
in which R1, R2, R3 and R4, identical or different, denote Z, OZ, COZ, COOZ, CONZZ ', C 6 -C 3 yle aryl or C7-C40 aralkyl or C 7 -C 40 alkylaryl optionally substituted by one or more groups chosen from OH, NH 2 , halogen, carboxy, or C1-C30 carbonyl alkoxy; 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 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 propellant selected from dimethyl ether, linear or branched alkanes containing from 2 to 6 carbon atoms or their mixtures.
2. Dispositif selon la revendication 1 , caractérisé par le fait que le composé de formule (1) est choisi parmi les composés suivants :2. Device according to claim 1, characterized in that the compound of formula (1) is chosen from the following compounds:
Le 2,4'-dihydroxy diphényl éther2,4'-dihydroxy diphenyl ether
Le 2-hydroxy 2'-éthyl diphényl éther2-hydroxy 2'-ethyl diphenyl ether
Le 2-hydroxy 2'-isopropyl diphényl éther2-hydroxy 2'-isopropyl diphenyl ether
Le 2-hydroxy 2'-méthyl diphényl éther - Le 2-hydroxy 2'-sec.butyl diphényl éther2-hydroxy 2'-methyl diphenyl ether - 2-hydroxy 2'-sec.butyl diphenyl ether
Le 2-hydroxy 2'-tert.butyl diphényl éther2-hydroxy 2'-tert.butyl diphenyl ether
Le 2-hydroxy 3-butanoyl diphényl éther2-hydroxy 3-butanoyl diphenyl ether
Le 2-hydroxy 3-propanoyl diphényl éther Le 2-hydroxy 4-formyl diphényl éther2-hydroxy 3-propanoyl diphenyl ether 2-hydroxy 4-formyl diphenyl ether
Le 2-hydroxy 4'-méthyl 5-formyl diphényl éther2-hydroxy 4'-methyl 5-formyl diphenyl ether
Le 2-hydroxy 5-butanoyl diphényl éther2-hydroxy 5-butanoyl diphenyl ether
Le 2-hydroxy 5-formyl diphényl éther2-hydroxy 5-formyl diphenyl ether
Le 2-hydroxy diphényl éther2-hydroxy diphenyl ether
Le 3-hydroxy 2'-méthyl diphényl éther3-hydroxy 2'-methyl diphenyl ether
Le 3-hydroxy 2'-sec.butyl diphényl éther3-hydroxy 2'-sec.butyl diphenyl ether
Le 3-hydroxy 2'-méthyl 4-n-propyl diphényl éther3-hydroxy 2'-methyl 4-n-propyl diphenyl ether
Le 3-hydroxy 3'-méthyI diphényl éther3-hydroxy 3'-methyl diphenyl ether
Le 3-hydroxy 3'-méthyl 4-n-propyl diphényl éther3-hydroxy 3'-methyl 4-n-propyl diphenyl ether
Le 3-hydroxy 4-(1 -hydroxy 2-méthylpropyl) diphényl éther3-hydroxy 4- (1-hydroxy 2-methylpropyl) diphenyl ether
Le 3-hydroxy 4-butanoyl diphényl éther3-hydroxy 4-butanoyl diphenyl ether
Le 3-hydroxy 4-butyl diphényl éther3-hydroxy 4-butyl diphenyl ether
Le 3-hydroxy 4-diméthylpropyl diphényl éther3-hydroxy 4-dimethylpropyl diphenyl ether
Le 3-hydroxy 4-diméthylpropyl 3'-méthyl diphényl éther3-hydroxy 4-dimethylpropyl 3'-methyl diphenyl ether
Le 3-hydroxy 4-hexyl diphényl éther3-hydroxy 4-hexyl diphenyl ether
Le 3-hydroxy 4-hexanoyl diphényl éther3-hydroxy 4-hexanoyl diphenyl ether
Le 3-hydroxy 4-dodécyl diphényl éther3-hydroxy 4-dodecyl diphenyl ether
Le 3-hydroxy 4-isobutanoyl diphényl éther3-hydroxy 4-isobutanoyl diphenyl ether
Le 3-hydroxy 4-isobutyl diphényl éther3-hydroxy 4-isobutyl diphenyl ether
Le 3-hydroxy 4-isopentanoyl diphényl éther3-hydroxy 4-isopentanoyl diphenyl ether
Le 3-hydroxy 4-isopropyl diphényl éther3-hydroxy 4-isopropyl diphenyl ether
Le 3-hydroxy 4'-isopropyl diphényl éther3-hydroxy 4'-isopropyl diphenyl ether
Le 3-hydroxy 4-n-butyl diphényl éther3-hydroxy 4-n-butyl diphenyl ether
Le 3τhydroxy 4-n-butyl diphényl éther3τhydroxy 4-n-butyl diphenyl ether
Le 3-hydroxy 4-n-pentyl diphényl éther3-hydroxy 4-n-pentyl diphenyl ether
Le 3-hydroxy 4-n-propyl diphényl éther3-hydroxy 4-n-propyl diphenyl ether
Le 3-hydroxy 4-pentanoyl diphényl éther3-hydroxy 4-pentanoyl diphenyl ether
Le 3-hydroxy 4-pentyl diphényl éther3-hydroxy 4-pentyl diphenyl ether
Le 3-hydroxy 4-phenyléthyl diphényl éther3-hydroxy 4-phenylethyl diphenyl ether
Le 3-hydroxy 2'-méthyl 4-phenyléthyl diphényl éther3-hydroxy 2'-methyl 4-phenylethyl diphenyl ether
Le 3-hydroxy 3'-méthyl 4-phenyléthyl diphényl éther3-hydroxy 3'-methyl 4-phenylethyl diphenyl ether
Le 3-hydroxy 4-propanoyl diphényl éther Le 3-hydroxy diphényl éther3-hydroxy 4-propanoyl diphenyl ether 3-hydroxy diphenyl ether
Le 3,4'-dihydroxy diphényl éther3,4'-dihydroxy diphenyl ether
Le 4,4'-dihydroxy diphényl éther4,4'-dihydroxy diphenyl ether
Le 4-hydroxy 2'- méthyl 5'-isopropyl diphényl éther4-hydroxy 2'-methyl 5'-isopropyl diphenyl ether
Le 4-hydroxy 2'- tert.butyl 5'-méthyl diphényl éther4-hydroxy 2'-tert.butyl 5'-methyl diphenyl ether
Le 4-hydroxy 2',5'-diméthyl diphényl éther4-hydroxy 2 ', 5'-dimethyl diphenyl ether
Le 4-hydroxy 2'-cyclohexyl 5'-méthyl diphényl éther4-hydroxy 2'-cyclohexyl 5'-methyl diphenyl ether
Le 4-hydroxy 2'-isopropyl 4'-éthyl diphényl éther4-hydroxy 2'-isopropyl 4'-ethyl diphenyl ether
Le 4-hydroxy 2'-isopropyl 4'-propyl diphényl éther4-hydroxy 2'-isopropyl 4'-propyl diphenyl ether
Le 4-hydroxy 2'-isopropyl 5'-méthyl diphényl éther4-hydroxy 2'-isopropyl 5'-methyl diphenyl ether
Le 4-hydroxy 2'-isopropyl diphényl éther4-hydroxy 2'-isopropyl diphenyl ether
Le 4-hydroxy 2'-isopropyl 4'-phényléthyl diphényl éther4-hydroxy 2'-isopropyl 4'-phenylethyl diphenyl ether
Le 4-hydroxy 3-(3-méthylbutyl) 4'-(3-méthylbutyl) diphényl éther4-hydroxy 3- (3-methylbutyl) 4 '- (3-methylbutyl) diphenyl ether
Le 4-hydroxy 4'-diméthylpropyl diphényl éther4-hydroxy 4'-dimethylpropyl diphenyl ether
Le 4-hydroxy 4'-éthyl diphényl éther4-hydroxy 4'-ethyl diphenyl ether
Le 4-hydroxy 4'-nonyl diphényl éther4-hydroxy 4'-nonyl diphenyl ether
Le 4-hydroxy 4'-phényléthyl diphényl éther4-hydroxy 4'-phenylethyl diphenyl ether
Le 4-hydroxy 4'-propyl diphényl éther4-hydroxy 4'-propyl diphenyl ether
Le 4-hydroxy 4'-trifluorométhyl diphényl éther4-hydroxy 4'-trifluoromethyl diphenyl ether
Le 4-hydroxy 4'-propanoyl diphényl éther4-hydroxy 4'-propanoyl diphenyl ether
Le 4-hydroxy diphényl éther4-hydroxy diphenyl ether
3. Dispositif selon l'une quelconque des revendications 1 et 2 , caractérisé par le fait que la concentration en composé(s) de formule (1) varie de 0.001 à 20%, de préférence de 0.01 à 15% et encore preferentiellement de 0.1 à 10% en poids rapport au poids total de la composition.3. Device according to any one of claims 1 and 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 more preferably from 0.1 at 10% by weight relative to the total weight of the composition.
4. Dispositif selon l'une quelconque des revendications 1 à 3, caractérisé par le fait que les alcanes sont choisis parmi le n-butane, le propane, l'isobutane et leurs mélanges.4. Device according to any one of claims 1 to 3, characterized in that the alkanes are chosen from n-butane, propane, isobutane and their mixtures.
5. Dispositif selon l'une quelconque des revendications 1 à 4 , caractérisée par le fait que la concentration en agent(s) propulseur(s) varie de 5 à 90% en poids par rapport au poids total de la composition pressurisée. 5. Device according to any one of claims 1 to 4, characterized in that the concentration of propellant (s) varies from 5 to 90% by weight relative to the total weight of the pressurized composition.
6. Dispositif selon l'une quelconque des revendications 1 à 5 , caractérisé par le fait que la concentration en agent(s) propulseur(s) varie de 15 à 70% en poids par rapport au poids total de la composition pressurisée.6. Device according to any one of claims 1 to 5, characterized in that the concentration of propellant (s) varies from 15 to 70% by weight relative to the total weight of the pressurized composition.
7. Dispositif selon l'une quelconque des revendications 1 à 6 , caractérisé par le fait que la composition contenant le ou les composés de formule (1) et le ou les agents propulseurs peuvent se trouver dans le même compartiment ou dans des compartiments différents dans le récipient aérosol.7. Device according to any one of claims 1 to 6, characterized in that the composition containing the compound (s) of formula (1) and the propellant (s) may be in the same compartment or in different compartments in the aerosol container.
8. Dispositif selon l'une quelconque des revendications 1 à 7 , caractérisé par le fait que la composition contient en plus au moins un actif déodorant et/ou un actif antitranspirant.8. Device according to any one of claims 1 to 7, characterized in that the composition additionally contains at least one deodorant active and / or an antiperspirant active.
9. Dispositif selon la revendication 8 , caractérisé par le fait que la composition aérosol contient au moins un actif déodorant choisi parmi le pyrrolidone carboxylate de zinc (plus communément appelé pidolate de zinc), le sulfate de zinc, le chlorure de zinc, le lactate de zinc, le gluconate de zinc et le phenoisulfonate de zinc, le 2,4,4'-trichloro-2'-hydroxydiphényléther (Triclosan), le 2,4-dichloro-2'-hydroxydiphényléther, le 3',4',5'-trichlorosalicylanilide, la 1-(3',4'- dichlorophenyl)-3-(4'-chlorophenyl)urée (triclocarban) ou le 3,7,11- triméthyldodéca-2,5, 10-triénol (Famesol) .9. Device according to claim 8, characterized in that the aerosol composition contains at least one deodorant active agent chosen from zinc pyrrolidone carboxylate (more commonly called zinc pidolate), zinc sulphate, zinc chloride, lactate zinc, zinc gluconate and zinc phenoisulfonate, 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) .
10. Dispositif selon la revendication 8, caractérisée par le fait que la composition aérosol contient un actif antitranspirant choisi parmi le chlorhydrate d'aluminium, l'aluminium chlorohydrex, l'aluminium chlorohydrex PEG, l'aluminium chlorohydrex PG, l'aluminium dichlorohydrate, l'aluminium dichlorohydrex PEG, l'aluminium dichlorohydrex PG, l'aluminium sesquichlorohydrate, l'aluminium sesquichlorohydrex PEG, l'aluminium sesquichlorohydrex PG, l'aluminium sulfate, l'aluminium zirconium octachlorohydrate, l'aluminium zirconium pentachlorohydrate, l'aluminium zirconium tetrachlorohydrate, l'aluminium zirconium trichlorohydrate, les complexes de métaux avec un acide aminé 10. Device according to claim 8, characterized in that the aerosol composition contains an antiperspirant active agent chosen from 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 with an amino acid
11. Dispositif selon la revendication 10, caractérisé par le fait que l'acide aminé utilisé avec les complexes de métaux est la glycine.11. Device according to claim 10, characterized in that the amino acid used with the metal complexes is glycine.
12. Dispositif selon la revendication 11 , caractérisé par le fait que les complexes sont choisis parmi l'aluminium zirconium octachlorohydréx GLY, l'aluminium zirconium pentachlorohydrex GLY, l'aluminium zirconium tetrachlorohydrate GLY et l'aluminium zirconium trichlorohydrate-GLY.12. Device according to claim 11, 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.
13. Dispositif selon l'une quelconque des revendications 8 à 12 , caractérisé par le fait que les actifs déodorants ou antitranspirants sont présents dans la composition à raison d'environ 0,001 à 20% en poids par rapport au poids total de la composition.13. Device according to any one of claims 8 to 12, characterized in that the deodorant or antiperspirant active agents are present in the composition in an amount of about 0.001 to 20% by weight relative to the total weight of the composition.
14. Dispositif selon la revendication 13, caractérisé par le fait que les actifs déodorants ou antitranspirants sont présents à raison d'environ 0,1 à 10% en poids par rapport au poids total de la composition.14. Device according to claim 13, characterized in that the deodorant or antiperspirant active agents are present in an amount of approximately 0.1 to 10% by weight relative to the total weight of the composition.
15. Dispositif selon l'une quelconque des revendications 1 à14, caractérisé par le fait que la composition comprenant le ou les composés de formule (1) est formulée dans un véhicule cosmetiquement acceptable qui contient de l'eau et/ou un ou plusieurs solvants organiques.15. Device according to any one of claims 1 to 14, characterized in that the composition comprising the compound or compounds of formula (1) is formulated in a cosmetically acceptable vehicle which contains water and / or one or more solvents organic.
16. Dispositif selon la revendication 15, caractérisé par le fait que le solvant organique est choisi parmi les monoalcools en CrC4,le propylène glycol, le dipropylène glycol ou leurs éthers.16. Device according to claim 15, characterized in that the organic solvent is chosen from CrC 4 monoalcohols, propylene glycol, dipropylene glycol or their ethers.
17. Dispositif selon la revendication 16, caractérisée par le fait que le solvant organique est Péthanol.17. Device according to claim 16, characterized in that the organic solvent is ethanol.
18. Dispositif selon l'une quelconque des revendications 1 à 17, caractérisé par le fait que la composition comprenant le ou les composés de formule (1) est formulée sous forme Φ émulsion eau-dans-huile, huile-dans-eau, ou d' émulsion triple éau-dans-huile-dans-eau 18. Device according to any one of claims 1 to 17, characterized in that the composition comprising the compound or compounds of formula (1) is formulated in the form Φ water-in-oil emulsion, oil-in-water, or of water-in-oil-in-water triple emulsion
19. Dispositif selon l'une quelconque des revendications 1 à 18, caractérisé par le fait que la composition comprenant le ou les composés de formule (1) contient un ou plusieurs adjuvants cosmétiques choisis parmi les corps gras, les gélifiants, les émollients, les adoucissants, les antioxydants, les opacifiants, les stabilisants, les agents anti-mousse, les agents hydratants, les vitamines, les parfums, les conservateurs, les tensioactifs, les charges, les séquestrants, les polymères, les propulseurs, les agents alcalinisants ou acidifiants, les parfums, les colorants, les pigments, les agents épaississants, ou tout autre ingrédient habituellement utilisé en cosmétique.19. Device according to any one of claims 1 to 18, characterized in that the composition comprising the compound or compounds of formula (1) contains one or more cosmetic adjuvants chosen from fatty substances, gelling agents, emollients, softeners, antioxidants, opacifiers, stabilizers, defoamers, moisturizers, vitamins, fragrances, preservatives, surfactants, fillers, sequestrants, polymers, propellants, alkalizing or acidifying agents , perfumes, dyes, pigments, thickening agents, or any other ingredient usually used in cosmetics.
20. Dispositif selon l'une quelconque des revendications 1 à 19, caractérisé par le fait que la composition comprenant le ou les composés de formule (1 ) se présente sous forme de lotion, de crème ou de gel fluide distribué en spray aérosol.20. Device according to any one of claims 1 to 19, characterized in that the composition comprising the compound or compounds of formula (1) is in the form of a lotion, cream or fluid gel distributed in aerosol spray.
21. Procédé de traitement des odeurs corporelles humaines et notamment axillaires par utilisation du dispositif décrit selon l'une quelconque des revendications 1 à 20. 21. A method of treating human body odors and in particular axillary odors by using the device described according to any one of claims 1 to 20.
PCT/FR2002/001788 2001-06-29 2002-05-28 Compositions containing a hydroxydiphenyl ether derivative inhibiting body odours WO2003002072A1 (en)

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FR0108660A FR2826572B1 (en) 2001-06-29 2001-06-29 COMPOSITIONS CONTAINING A HYDROXYDIPHENYL ETHER DERIVATIVE INHIBITING THE DEVELOPMENT OF BODY ODORS
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EP2719700A1 (en) 2008-01-09 2014-04-16 Amura Therapeutics Limited Tetrahydrofuro(3,2-b)pyrrol-3-one derivatives as inhibitors of cysteine proteinases
US10533033B2 (en) * 2015-01-06 2020-01-14 Immunovaccine Technologies Inc. Lipid A mimics, methods of preparation, and uses thereof

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US5098693A (en) * 1989-07-21 1992-03-24 Cast Blast Anti-irritant spray for use with cast and method of application
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WO2003086338A1 (en) * 2002-04-12 2003-10-23 Ciba Specialty Chemicals Holding Inc. Use of hydroxydiphenyl ether derivatives as arylsulfatase- inhibitors in deodorants and antiperspirants
EP2719700A1 (en) 2008-01-09 2014-04-16 Amura Therapeutics Limited Tetrahydrofuro(3,2-b)pyrrol-3-one derivatives as inhibitors of cysteine proteinases
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US10988500B2 (en) 2015-01-06 2021-04-27 Immunovaccine Technologies Inc. Lipid A mimics, methods of preparation, and uses thereof

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