WO2002102339A1 - Emulsion parfumante transparente stable - Google Patents

Emulsion parfumante transparente stable Download PDF

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Publication number
WO2002102339A1
WO2002102339A1 PCT/IB2001/001047 IB0101047W WO02102339A1 WO 2002102339 A1 WO2002102339 A1 WO 2002102339A1 IB 0101047 W IB0101047 W IB 0101047W WO 02102339 A1 WO02102339 A1 WO 02102339A1
Authority
WO
WIPO (PCT)
Prior art keywords
emulsion
oil
perfuming
origin
water
Prior art date
Application number
PCT/IB2001/001047
Other languages
English (en)
Inventor
Thierry Stora
Original Assignee
Firmenich S.A.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Firmenich S.A. filed Critical Firmenich S.A.
Priority to PCT/IB2001/001047 priority Critical patent/WO2002102339A1/fr
Priority to CA002448496A priority patent/CA2448496C/fr
Priority to JP2003503196A priority patent/JP4072119B2/ja
Priority to PCT/IB2002/001964 priority patent/WO2002100372A2/fr
Priority to DE60222897T priority patent/DE60222897T2/de
Priority to AT02733098T priority patent/ATE375139T1/de
Priority to ES02733098T priority patent/ES2294137T3/es
Priority to BRPI0210303-6A priority patent/BR0210303B1/pt
Priority to EP02733098A priority patent/EP1399124B1/fr
Publication of WO2002102339A1 publication Critical patent/WO2002102339A1/fr
Priority to US10/723,922 priority patent/US7226901B2/en
Priority to HK04107386A priority patent/HK1064594A1/xx

Links

Classifications

    • 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
    • A61K8/69Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing fluorine
    • A61K8/70Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing fluorine containing perfluoro groups, e.g. perfluoroethers
    • 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
    • A61K8/06Emulsions
    • 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
    • A61K8/345Alcohols containing more than one hydroxy group
    • 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
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • 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
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/90Block copolymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00Formulations or additives for perfume preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/26Optical properties
    • A61K2800/262Transparent; Translucent

Definitions

  • the present invention relates to the field of perfumery. It concerns more particularly an alcohol-free perfuming composition in the form of a fluid, transparent water-in-oil or oil-in- water emulsion.
  • the emulsion of the invention is characterised by an outstanding stability, the densities of the respective oily and aqueous phases being particularly close to one another.
  • the stabilisation of formulations comprising high fragrance levels constitutes therefore a specific and challenging problem, notably different from that of the stabilisation of a cosmetic emulsion, which comprises other kinds of components, the nature of which is generally dependent on the type of the final cosmetic product (typical active ingredients include natural or synthetic oils, hydrocarbons, halogenated carbons, esters of mineral acids, silicones). Furthermore, such cosmetic compositions contain very low amoimts of perfuming ingredients.
  • an essential requirement sought in the formulation of an emulsion of any kind is the physical stability, without which the emulsion will soon revert back to separate bulk phases.
  • One typical phenomenon associated with physical instability is constituted by the upward and downward movement of dispersed droplets relative to the continuous phase, termed creaming or sedimentation respectively.
  • the factors that influence the rate of sedimentation or creaming are the diameter of the suspended droplets, the viscosity of the suspending medium and the difference in densities between the dispersed phase and the dispersion medium.
  • the prior art discloses a first means to avoid this destabilisation phenomenon, consisting in reducing the particle size of the dispersed system, which contributes greatly toward overcoming or minimising creaming.
  • microemulsions are liquid dispersions of water and oil that are made homogeneous, transparent and stable by the addition of relatively large amounts of a surfactant and a co-surfactant. While emulsions are unstable, microemulsions are stable and, therefore, they are formed spontaneously when oil, water, surfactants and co- surfactants are mixed together. Conversely, emulsions require input of considerable mechanical energy for their preparation. Furthermore, microemulsion droplets have a narrow droplet size distribution with a mean diameter range of approximately 5-50 nm.
  • a microemulsion does not constitute a suitable dispersed system for the present invention, which has to be in the form of an emulsion.
  • nanoemulsion characterised by an average size of the oily phase droplets below ca. 30-75 nm.
  • the droplets are small enough to make the emulsion translucent or partially transparent.
  • the invention now provides a transparent, fluid, water-in-oil or oil-in- water emulsion characterised by the fact that the densities of the respective continuous and dispersed phases have almost matching values.
  • This solution to the well-known problem of physical instability, and more particularly of creaming and sedimentation, specifically adapted to a dispersed system of the emulsion type has been achieved thanks to the presence of a specific additive in the oily phase of the emulsion, namely a volatile fluorinated oil having a density higher than 1.
  • This class of compounds has already been used in some kinds of emulsions.
  • EP 1064929 discloses the use of such a volatile fluorinated oil in a cosmetic composition for attenuating skin deficiencies and for giving a matt skin appearance.
  • the cosmetic composition there-disclosed is not only totally distinct, from a formulation point of view, from a perfuming composition, but also the fluorinated oil is used in this prior art for a technical effect consisting in modifying the skin appearance, thus an aim distinct from that achieved by the present invention, i.e. the stabilisation of an emulsion.
  • EP 1064989 also discloses a cosmetic emulsion comprising a volatile fluorinated oil.
  • a volatile fluorinated oil is very difficult to stabilise and may provoke an instability phenomenon such as foaming, demixing and changes in viscosity, and that it has thus to be used in combination with a specific surfactant, able to stabilise the emulsion.
  • a volatile fluorinated oil is thus very difficult to stabilise.
  • a perfuming composition in the form of an emulsion, could be advantageously stabilised by minimising the difference existing between the densities of the respective continuous and dispersed phases and that such an effect could be achieved by adding to the oily phase of the emulsion a volatile fluorinated oil having a density higher than one, without any need of combining said ingredient with a specific surfactant such as disclosed in EP 1064989.
  • composition of the invention is also alcohol-free, which is an advantage henceforth sought in such formulations.
  • an object of the present invention to provide an alcohol free perfuming composition in the form of a transparent water-in-oil or oil-in-water emulsion with an outstanding stability, characterised by the fact that the difference between the density of the oily phase and that of the aqueous phase in less than or equal to 0.005, preferably less than or equal to 0.003.
  • the emulsion of the invention is advantageously particularly resistant to phenomena such as creaming and sedimentation and constitutes a novel, effective solution to the instability problems known in the prior art compositions.
  • a substance can be added to a perfuming composition which is an emulsion and provide the technical effect of bringing closer the densities of the respective phases of this emulsion.
  • a volatile fluorinated oil having a density higher than 1 constitutes such a substance.
  • Another object of the invention is thus provided by a perfuming composition in the form of an emulsion, wherein the oily phase comprises a certain amount of a volatile fluorinated oil having a density higher than 1.
  • the invention also concerns the use of said ingredient as a stabilisation agent in an emulsion.
  • the perfuming composition of the invention is in the form of a transparent water-in-oil or oil-in-water emulsion susceptible of being sprayed, comprising an aqueous phase and an oily phase containing at least 3% by weight of perfuming ingredients relative to the total weight of the composition, wherein the difference between the density of the oily phase and that of the aqueous phase is less than or equal to 0.005, preferably less than or equal to 0.003.
  • This technical effect may be achieved when the oily phase contains a volatile fluorinated oil having a density higher than 1.
  • What is intended here by perfuming composition is a perfume vehicle, the main function of which is to impart, enhance or modify the odoriferous properties of a product.
  • the continuous phase is formed by water (aqueous phase) and the dispersed phase is formed by the oil (oily phase) which is essentially formed of perfuming ingredients.
  • the emulsion is a water-in-oil or inverse emulsion when the continuous phase is formed by the oil wherein the water is dispersed.
  • the latter type of emulsion is preferred according to one embodiment of the invention.
  • the emulsion according to the present invention meets a certain number of criteria required in the field of perfumery, for applications such as perfumes, eaux de toilette, or Colognes.
  • the composition of the invention is alcohol free. There is at present a demand for such types of compositions, particularly from consumers with sensitive skins or whose skins are often exposed to the sun.
  • composition of the invention is fluid, or in other words susceptible of being sprayed.
  • its viscosity is lower than 10 Pa.s, independently of the nature of the emulsion.
  • the emulsion is transparent, a desirable quality in the field of perfumery.
  • the transparency is achieved thanks to the addition to the perfuming compositions of ingredients capable of modifying the refractive indices of the two phases, so as to form a transparent emulsion.
  • the particular solid or liquid ingredients used to act either on the oily or on the aqueous phase in order to achieve transparency are described in WO 00/33804, the contents of which are hereby included by reference, namely as regards the citation of such ingredients.
  • the refractive index of a finished perfuming composition according to the invention has a value between ca. 1.40 and 1.44.
  • the present invention brings an advantageous improvement to the known transparent emulsions.
  • the addition of a certain ingredient to the oily phase of the emulsion could significantly improve the physical stability of the emulsion, in particular with regard to the creaming and sedimentation problems.
  • the addition of such an ingredient to the oily phase of the emulsion makes it possible to narrow the difference between the respective densities of the two phases, so as to bring it within the limit defined above, namely lower or equal to 0.005, or even 0.003 in preferred embodiments.
  • the invention brings thus a novel solution to the known problem of physical stability, by providing means for acting on the relative densities of both phases.
  • the above-mentioned agent which will be used to act on the oily phase must be soluble in the latter.
  • the agent is chosen with a density higher than 1.
  • the fluorinated oil used according to the present invention is selected from the group consisting of hydrofluoroethers such as methoxynonafluorobutane or ethoxynonafluorobutane.
  • the ingredient added to the oily phase of the emulsion is methoxynonafluorobutane.
  • the volatile fluorinated oil may also be used in mixture with a less volatile fluorinated oil such as a perfluoroalcane.
  • Perfluorodecaline is an example of a suitable perfluoroalcane for this purpose.
  • the amount of fluorinated oil added to the oily phase is comprised between 5 and 50% by weight relative to the oily phase.
  • the emulsions of the invention can contain from 5 to 50% by weight, preferably from 10 to 35% by weight, of dispersed phase and from 50 to 95% by weight, preferably 65 to 90% by weight, of continuous phase. These values are relative to the total weight of the emulsion and are independent of the fact that the compositions of the invention are in the form of a water-in-oil or an oil-in-water emulsion.
  • the oily phase is essentially formed of perfuming ingredients. Typically it comprises from 15 to 60%, preferably from 20 to 50% by weight of perfuming ingredients.
  • the aqueous phase comprises from 20 to 65% of water.
  • composition of the invention may further contain at least one surfactant.
  • This surfactant will be used in a proportion of 0 to 8%, preferably 0.1 to 5% by weight, relative to the total weight of the emulsion. The best results were obtained using 2 to 5% by weight of surfactant.
  • surfactants can be used in the context of the invention.
  • non-ionic, cationic, anionic, the amphoteric surfactants and the phospholipids which may all be used in the present invention.
  • a non-ionic surfactant or a mixture of two non-ionic surfactants there is used.
  • the ethoxylated nonylphenol comprising 9 to 10 units of ethyleneglycol (on sale under the name of Triton ® N-101 ; origin : Fluka, Switzerland) or the ethoxylated undecanol comprising 8 units of ethyleneglycol (on sale under the name of Imbentin ® 0800 ; origin : Kolb AG, Switzerland)
  • Imbentin ® 0800 origin : Kolb AG, Switzerland
  • Tween ® (origin : ICI, England), such as Tween ® 20 [polyoxyethylene (20) sorbitan monolaurate], Tween ® 40 [polyoxyethylene (20) sorbitan monopalmitate], Tween ® 60 [polyoxyethylene (20) sorbitan monostearate] and Tween ® 80 [polyoxyethylene (20) sorbitan monooleate], and the surfactants commercialised under the name of Span ® (origin : ICI, England), such as Span ® 20 (sorbitan monolaurate), Span ® 40 (sorbitan monopalmitate), Span ® 60 (sorbitan monostearate), and Span ® 80 (sorbitan monooleate).
  • Cremophor ® RH40 and RH60 oil : BASF AG, Germany, which are ethoxylated hydrogenated ricin oils
  • Genapol ® [origin : Hoechst AG, Germany, a sodium (alcohol polyglycol ether) laurylsulfate]
  • Poloxamer ® 407 a diblock copolymer of ethyleneoxyde and propyleneoxyde, also commercialised under the names of Pluronic ' F 127 and Pluracare" F 127, origin : BASF AG, Germany)
  • Tetronic ® (origin : BASF AG, Germany)
  • DC 3225 C, DC 5200, DC 193 (origin : Dow Corning, USA)
  • Abil ® Em 97 (origin : Goldschmidt).
  • the perfuming ingredients that can be used in the present invention are all the ingredients commonly used in perfumery. These ingredients shall not be described in greater detail here, as their description cannot be exhaustive and the skilled person is able to choose them using his general knowledge and as a function of the desired olfactory effect. These perfuming ingredients belong to a variety of chemical classes, as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpernic hydrocarbons, heterocyclic nitrogen- or sulfur- containing compounds, as well as essential oils of natural and synthetic origin. Many of these ingredients are furthermore described in reference textbooks such as the book of S.
  • the emulsion of the invention can be easily prepared by conventional mixing and homogenising methods, which therefore do not require a more detailed description here.
  • emulsions are created with an average drop size above 200 nm, preferably below 1 ⁇ m.
  • a water-in-oil emulsion containing a perfuming base has been prepared with the below- specified ingredients. Incorporation of the fluorinated oil was done after emulsification of the other ingredients by a current method in the art.
  • the perfuming base was obtained by mixing the following ingredients :
  • Phenethylol 9 Petitgrain essential oil 63
  • the density of each of the two phases of the composition was measured at 30° on a density meter (DMA 4500 ; Anton Paar).
  • the density of the aqueous phase was 1.0209 and that of the oily phase was 1.0249, thus forming a stable transparent emulsion.
  • a water-in-oil emulsion containing a perfuming base has been prepared with the below- specified ingredients. Incorporation of the fluorinated oil was done after emulsification of the other ingredients by a current method in the art.
  • the density of each of the two phases of the composition was measured at 30° on a density meter (DMA 4500 ; Anton Paar).
  • the density of the aqueous phase was 1.0193 and that of the oily phase was 1.0218, thus forming a stable transparent emulsion.
  • the respective refractive index of each phase was also measured and the difference between the two phases was of 0.0086.

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

Abstract

La présente invention concerne une composition parfumante particulièrement stable qui se présente sous la forme d'une émulsion liquide eau dans huile ou huile dans eau et qui est obtenue par addition dans la phase huileuse d'une substance capable de rapprocher les densités des phases dispersées et continues respectives.
PCT/IB2001/001047 2001-06-11 2001-06-14 Emulsion parfumante transparente stable WO2002102339A1 (fr)

Priority Applications (11)

Application Number Priority Date Filing Date Title
PCT/IB2001/001047 WO2002102339A1 (fr) 2001-06-14 2001-06-14 Emulsion parfumante transparente stable
AT02733098T ATE375139T1 (de) 2001-06-11 2002-05-29 Stabile durchsichtige parfüm-emulsion
JP2003503196A JP4072119B2 (ja) 2001-06-11 2002-05-29 安定化された透明な香料エマルション
PCT/IB2002/001964 WO2002100372A2 (fr) 2001-06-11 2002-05-29 Emulsion parfumee transparente et stable
DE60222897T DE60222897T2 (de) 2001-06-11 2002-05-29 Stabile durchsichtige parfüm-emulsion
CA002448496A CA2448496C (fr) 2001-06-11 2002-05-29 Emulsion parfumee transparente et stable
ES02733098T ES2294137T3 (es) 2001-06-11 2002-05-29 Emulsion perfumante transparente y estable.
BRPI0210303-6A BR0210303B1 (pt) 2001-06-11 2002-05-29 Composição perfumante livre de álcool, e, processo para a preparação da mesma
EP02733098A EP1399124B1 (fr) 2001-06-11 2002-05-29 Emulsion parfumee transparente et stable
US10/723,922 US7226901B2 (en) 2001-06-11 2003-11-24 Stable transparent perfuming emulsion
HK04107386A HK1064594A1 (en) 2001-06-11 2004-09-24 Stable transparent perfuming emulsion

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IB2001/001047 WO2002102339A1 (fr) 2001-06-14 2001-06-14 Emulsion parfumante transparente stable

Publications (1)

Publication Number Publication Date
WO2002102339A1 true WO2002102339A1 (fr) 2002-12-27

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Application Number Title Priority Date Filing Date
PCT/IB2001/001047 WO2002102339A1 (fr) 2001-06-11 2001-06-14 Emulsion parfumante transparente stable

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WO (1) WO2002102339A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006097759A1 (fr) * 2005-03-18 2006-09-21 Quest International Services B.V. Compositions de parfum
WO2007106213A2 (fr) * 2006-02-24 2007-09-20 Dow Global Technologies Inc. Emulsion d'une phase d'huile fluoree liquide dans une phase aqueuse liquide

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2771290A1 (fr) * 1997-11-26 1999-05-28 Archimex Pibs Utilisation des hydrofluoroethers en tant qu'agents de dissolution de composes aromatiques pour la realisation de compositions cosmetiques
WO2000033804A1 (fr) * 1998-12-08 2000-06-15 Firmenich S.A. Composition parfumante transparente
FR2797764A1 (fr) * 1999-08-26 2001-03-02 Lvmh Rech Composition non ethanolique comprenant un hydrofluoroether perfluore et au moins un co-solvant autre que l'eau et l'ethanol comprenant un ester d'un polyacide et son utilisation dans des compositions parfumantes

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2771290A1 (fr) * 1997-11-26 1999-05-28 Archimex Pibs Utilisation des hydrofluoroethers en tant qu'agents de dissolution de composes aromatiques pour la realisation de compositions cosmetiques
WO2000033804A1 (fr) * 1998-12-08 2000-06-15 Firmenich S.A. Composition parfumante transparente
FR2797764A1 (fr) * 1999-08-26 2001-03-02 Lvmh Rech Composition non ethanolique comprenant un hydrofluoroether perfluore et au moins un co-solvant autre que l'eau et l'ethanol comprenant un ester d'un polyacide et son utilisation dans des compositions parfumantes

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006097759A1 (fr) * 2005-03-18 2006-09-21 Quest International Services B.V. Compositions de parfum
WO2007106213A2 (fr) * 2006-02-24 2007-09-20 Dow Global Technologies Inc. Emulsion d'une phase d'huile fluoree liquide dans une phase aqueuse liquide
WO2007106213A3 (fr) * 2006-02-24 2011-09-01 Dow Global Technologies Inc. Emulsion d'une phase d'huile fluoree liquide dans une phase aqueuse liquide

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