WO2018220147A1 - Parfums sous forme de microémulsions aqueuses - Google Patents

Parfums sous forme de microémulsions aqueuses Download PDF

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Publication number
WO2018220147A1
WO2018220147A1 PCT/EP2018/064389 EP2018064389W WO2018220147A1 WO 2018220147 A1 WO2018220147 A1 WO 2018220147A1 EP 2018064389 W EP2018064389 W EP 2018064389W WO 2018220147 A1 WO2018220147 A1 WO 2018220147A1
Authority
WO
WIPO (PCT)
Prior art keywords
microemulsion
formula
surfactant
sodium
group
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/EP2018/064389
Other languages
English (en)
French (fr)
Inventor
Oriana BOUCENNA VERDIER
Véronique RATAJ-NARDELLO
Jean-Marie Aubry
Grégory DOUYERE
Corentine MAINGUY
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chanel Parfums Beaute SAS
Universite de Lille
Original Assignee
Chanel Parfums Beaute SAS
Universite de Lille
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 Chanel Parfums Beaute SAS, Universite de Lille filed Critical Chanel Parfums Beaute SAS
Priority to EP18730991.9A priority Critical patent/EP3630057B1/fr
Priority to JP2019566073A priority patent/JP2020521787A/ja
Priority to KR1020197036592A priority patent/KR20200031565A/ko
Priority to US16/618,195 priority patent/US20200179247A1/en
Publication of WO2018220147A1 publication Critical patent/WO2018220147A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/06Emulsions
    • A61K8/068Microemulsions
    • 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
    • A61K8/46Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • 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
    • A61K8/46Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • 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
    • A61K8/60Sugars; Derivatives thereof
    • A61K8/602Glycosides, e.g. rutin
    • 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
    • A61K2800/10General cosmetic use
    • 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
    • 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
    • A61K2800/30Characterized by the absence of a particular group of ingredients
    • 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
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59Mixtures
    • A61K2800/596Mixtures of surface active compounds

Definitions

  • the invention relates to volatile aqueous perfume microemulsions based on the use of solvo-surfactants.
  • the perfumes comprise as solvents alcohols, such as ethanol or isopropanol.
  • solvents alcohols such as ethanol or isopropanol.
  • the use of these solvents has a number of disadvantages: they are very volatile and flammable, which causes a certain danger in their production, and to some extent, their use.
  • their own smell can interfere with that of the perfume.
  • these scents can cause drying, especially in consumers with sensitive skin.
  • thermodynamic stability of the microemulsion is related to the thermodynamic stability of the microemulsion, the non-stick nature of it and the absence of residue on the skin or clothing. It is therefore important to be able to prepare them using as little surfactant as possible.
  • the present invention aims to provide aqueous microemulsions, transparent, substantially free of ethanol, containing at least one hydrophobic perfuming substance (preferably at least 3% and preferably about 10% perfume), and at least one solvo-surfactant volatile.
  • odoriferous or perfume microemulsions are stable, and include as few substances as possible causing undesirable effects, particularly on the skin and / or the environment.
  • a substance is “volatile” when its boiling point is below 250 ° C at atmospheric pressure.
  • the "non-volatile” compounds have a boiling point above 250 ° C at atmospheric pressure.
  • solvo-surfactant preferably volatile, which is a monoalkylated glycerol derivative of formula (I) below:
  • oil-in-water microemulsion is meant a liquid system in which an oily (or hydrophobic) phase is dispersed in an aqueous (or hydrophilic) continuous phase, so as to form drops with a diameter of less than 100 nm. .
  • hydrophobic substance is meant a pure body or a mixture insoluble or very slightly soluble in water, by nature.
  • One possible method for determining the hydrophobicity of the substances is to measure their solubility in different solvents or the retention time on a chromatographic column (by high performance liquid chromatography HPLC) of said hydrophobic substance.
  • terpenoids is meant derivatives of terpenes, for example alcohols, phenols, ketones, aldehydes, esters or ethers.
  • terpenes pinenes, camphenes, limonene, cadinene, carina, caryophyllene,
  • esters linalyl acetate, menthyl acetate, geranyl acetate, geranyl succinate, phenols: thymol, carvacrol, eugenol, isoeugenol,
  • Essential oils can be ylang-ylang, bergamot, eucalyptus, lavender, lavandin, lemongrass, patchouli, peppermint, pine, rose, coriander, shiu, sage , Geranium, Palmarosa, LitseaCubeba, Lemon, Lemongrass, Orange Blossom, Grapefruit, Lime, Mandarin, Tangerine, Orange, Cajeput, Camphor, Rosemary, Anise green, star anise, fennel, basil, tarragon, clove, pepper, thyme, sassafras, wormwood, sagebrush, cedar, hyssop, tagetes, rue, elemi, galbanum, juniper berries, cabreuva, gaiac wood, sandalwood, vetiver, ambrette, angelica, rhizome of iris, carrot, celery, caraway , lovage, parsley, cinnamon, cardamom, ginger
  • the amount of perfuming hydrophobic substance in the microemulsions of the invention is 1% to 15% by weight, preferably 5% to 12% by weight relative to the total weight of microemulsion.
  • solvo-surfactant an amphiphilic compound, which combines certain properties of the surfactants, in particular the reduction of the surface tension water / air and
  • FIRE I LLE OF REM PLACEM ENT (RULE 26) interfacial oil / water, self-association ability in water, and some solvent properties, including the ability to evaporate without leaving any residue.
  • the solvo-surfactant present in the microemulsion of the invention is the monoalkylated glycerol derivative of formula (I) as defined above, namely:
  • FIRE I LLE OF REM PLACEM ENT (RULE 26) R 'is methyl, is 1-methoxy-3-pentoxypropan-2-ol. It is called "C501" in the examples of this application.
  • the solvo-surfactant present in the microemulsion of the invention is the monoalkylated glycerol derivative of formula (I) in which the "alkyl” group is a linear alkyl group comprising 3, 4 or 5 carbon atoms, R is a methyl group and R 'is H.
  • the solvo-surfactant present in the microemulsion of the invention is the monoalkylated glycerol derivative of formula (I) as defined above in which the "alkyl” group is a linear alkyl group comprising 5 carbon atoms.
  • This compound is 2-methoxy-3-pentoxypropan-1-ol, called "C510".
  • surfactant is meant a compound of amphiphilic nature, nonvolatile, having a hydrophilic and polar part, and an apolar hydrophobic part.
  • a surfactant lowers the surface tension of the aqueous solutions and decreases the interfacial tension between the water and an immiscible organic liquid. It thus solubilizes two immiscible phases, such as water and oil, by interacting with its polar part with water and its non-polar part with the oil.
  • the surfactant present in the microemulsion according to the invention is an anionic surfactant, namely a surfactant whose hydrophilic part is negatively charged.
  • Anionic surfactants have proved to be the most effective, in the context of the invention, with respect to nonionic, amphoteric or cationic surfactants.
  • the term "more effective" is intended to mean the introduction of a surfactant in a smaller quantity to form a microemulsion.
  • M + is Na + , K + , NH 4 , (HOCH 2 CH 2 ) 3 NH + , or
  • M + represents Na + , K + , NH 4 + , (HOCH 2 CH 2 ) 3 NH 4 alkylarylsulphonates of formula:
  • the Applicant has demonstrated that the combination of at least one anionic surfactant and at least one alkylglucoside makes it possible to increase the cloud point of the microemulsion.
  • this synergistic effect also has a positive impact on the amount of solvo-surfactant introduced into the microemulsion.
  • anionic surfactant and alkylglucoside it is possible to use amounts of
  • FIRE I LLE OF REM PLACEM ENT (RULE 26) solvosurfactif weaker, namely ranging from 4% to 10% by weight relative to the total weight of the microemulsion.
  • a quantity of 5% of solvosurfactant makes it possible to obtain a stable microemulsion and a perfect solubilization of the hydrophobic perfuming substance.
  • the decrease in the amount of solvo-surfactant is in favor of the amount of water that can be increased.
  • the aqueous character of the microemulsion is thus increased.
  • the quantity of anionic surfactant is less than or equal to 2% by weight relative to the total weight of microemulsion
  • the amount of alkylglucoside is from 0.5% to 13% by weight relative to the total weight of microemulsion, and preferably from 0.5% to 8%.
  • the anionic surfactant: alkylglucoside ratio is from 1: 4 to 1: 12, and preferably from 1: 4 to 1: 10.
  • the microemulsion according to the invention is substantially free of ethanol, ie it comprises less than 3% by weight of ethanol, preferably less than 2% by weight of ethanol, preferably less than 1% by weight of ethanol. ethanol. More preferably, it is devoid of ethanol, i.e. it contains 0% by weight of ethanol.
  • microemulsion according to the invention makes it possible in particular to obtain an aqueous perfuming composition having a transparency similar to an alcoholic product, without touching greasy or sticky, and leaving no traces or residues on the tissues or the skin.
  • the microemulsion according to the invention may comprise from 0.01% to
  • the microemulsion according to the invention may comprise, in a nonlimiting manner, one or more of the following additives:
  • an antifoam agent chosen from decamethylcyclopentasiloxane, dimethicone, cetyl dimethicone, dimethyl copolyol, dimethiconol, hexamethyldisiloxane, hexamidine diisethionate, hexyl alcohol, hexyldeceth-2 and isopropyl alcohol; phenyl disiloxane, phenyl trimethicone, polysilicone-10, polysilicone-7, polysilicone-8, propyl alcohol, silica dimethyl silylate, silica silylate, simethicone, tetramethyl decynediol and trimethylsiloxysilicate;
  • a preservative chosen for example from sodium benzoate, potassium benzoate, sodium salicylate, caprylyl glycol, pentylene glycol, ethylhexylglycerine, chlorphenesine, chlorhexidine, chlorhexidine digluconate, methylisothiazolinone, methylparaben, propylparaben, phenethyl alcohol and phenoxyethanol;
  • antioxidant chosen, for example, from BHA, BHT and tocopherol.
  • microemulsions according to the invention have a stable fragrance quality over time corresponding to the standard life of a cosmetic product, and stable in temperature from 5 to 45 ° C., which corresponds to the exposure and reaction temperatures. use of a cosmetic product.
  • FIRE I LLE OF REM PLACEM ENT (RULE 26) - Safety, which is the ability of a composition not to produce adverse effects once applied to the skin of the user.
  • the microemulsions of the invention are thermodynamically stable and have a transparent or translucent appearance and even more advantageously, the microemulsions of the invention are thermodynamically stable and have a transparent or translucent appearance for at least one or two years.
  • the present invention also relates to the use of a microemulsion according to the invention, for the preparation of a fine perfumery composition, or a cosmetic composition or personal hygiene.
  • Microemulsions can be used in cosmetics. They may then contain in particular, and without this list being limiting, one or more of the compounds chosen from silicones, paraffin oil, isooctane, isodecane, squalene, squalane, sebum and the lanolin.
  • the aim of this test is to classify solvo-surfactants according to their ability to solubilize (or not) gamma-undecalactone.
  • SUBSTITUTE SHEET (RULE 26) Formulas containing 5% gamma-undecalactone, 4.4% SDS (anionic surfactant), X% solvo-surfactant and QSP on water were made.
  • the solvo-surfactant having the best abilities to solubilize the hydrophobic perfuming substance is C510.
  • fragrance juice (P) was prepared:
  • formulations A, B, C, D and E must be temperature stable over a range of 5 ° C to 45 ° C.
  • the formulations are therefore placed in a bath at 5 ° C. and at 45 ° C. for 24 hours.
  • composition D has all the benefits of the invention through the implementation of a judicious ratio "surfactant: alkylglucoside” which is 1: 6, to obtain an aqueous formulation rich in water (> to 85%) in the presence of a small amount of solvo-surfactant (5%).
  • a microemulsion of the invention namely the formulation D described in the previous example 3, which comprises the solvo-surfactant C510, is compared with two other microemulsions (formulations D1 and D2) which respectively comprise hexylene glycol and propylene glycol instead of solvo-surfactant C510.
  • Hexylene glycol and propylene glycol do not correspond to formula (I) of the solvo-surfactant of the invention.
  • the heptyl glucoside used is that sold by Seppic under the name "Sepiclear G7".
  • the sodium lauryl sulphate (SDS) used is that marketed by BASF under the name "Texaplon LS30"
  • formulations D, D1 and D2 must be temperature stable over a range of 5 ° C to 45 ° C.
  • formulation D is clear whereas formulations D1 and D2 are already opalescent.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Cosmetics (AREA)
PCT/EP2018/064389 2017-06-01 2018-05-31 Parfums sous forme de microémulsions aqueuses Ceased WO2018220147A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP18730991.9A EP3630057B1 (fr) 2017-06-01 2018-05-31 Parfums sous forme de microémulsions aqueuses
JP2019566073A JP2020521787A (ja) 2017-06-01 2018-05-31 水性マイクロエマルジョンの形態の香水
KR1020197036592A KR20200031565A (ko) 2017-06-01 2018-05-31 수성 마이크로에멀전 형태의 퍼퓸
US16/618,195 US20200179247A1 (en) 2017-06-01 2018-05-31 Perfumes in the form of aqueous microemulsions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1754850 2017-06-01
FR1754850A FR3066913B1 (fr) 2017-06-01 2017-06-01 Parfums sous forme de microemulsions aqueuses

Publications (1)

Publication Number Publication Date
WO2018220147A1 true WO2018220147A1 (fr) 2018-12-06

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PCT/EP2018/064389 Ceased WO2018220147A1 (fr) 2017-06-01 2018-05-31 Parfums sous forme de microémulsions aqueuses

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US (1) US20200179247A1 (https=)
EP (1) EP3630057B1 (https=)
JP (1) JP2020521787A (https=)
KR (1) KR20200031565A (https=)
FR (1) FR3066913B1 (https=)
WO (1) WO2018220147A1 (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3669859A1 (en) * 2018-12-20 2020-06-24 Chanel Inc. Aqueous perfumes

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113354804B (zh) * 2020-12-31 2022-06-28 山东金智瑞新材料发展有限公司 一种脂肪醇聚氧丙烯醚含氧酸及其盐
WO2022245837A1 (en) * 2021-05-17 2022-11-24 P2S Science, Inc. Terpene ester surfactants
US12209069B2 (en) 2021-05-17 2025-01-28 P2 Science, Inc. Fatty acid terpene alcohol esters
US12215120B1 (en) 2021-05-17 2025-02-04 P2 Science, Inc. Terpene O-glycosides
US12528991B2 (en) 2021-07-15 2026-01-20 P2 Science, Inc. Citronellol alkoxylate surfactants
WO2026008596A1 (en) * 2024-07-03 2026-01-08 Firmenich Sa Ethanol-free emulsions and uses thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0003088A1 (fr) 1978-01-10 1979-07-25 COMMISSARIAT A L'ENERGIE ATOMIQUE Etablissement de Caractère Scientifique Technique et Industriel Olfactomètre différentiel
EP2340804A1 (en) * 2009-12-31 2011-07-06 Takasago International Corporation Fragrance microemulsion compositions
FR2998476A1 (fr) * 2012-11-26 2014-05-30 Univ Lille 1 Sciences & Technologies Microemulsions aqueuses volatiles de parfums et d huiles essentielles basees sur l utilisation de solvo- surfactifs
WO2014090959A1 (en) * 2012-12-13 2014-06-19 Firmenich Sa Ethanol-free microemulsion perfuming compositions

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0003088A1 (fr) 1978-01-10 1979-07-25 COMMISSARIAT A L'ENERGIE ATOMIQUE Etablissement de Caractère Scientifique Technique et Industriel Olfactomètre différentiel
EP2340804A1 (en) * 2009-12-31 2011-07-06 Takasago International Corporation Fragrance microemulsion compositions
FR2998476A1 (fr) * 2012-11-26 2014-05-30 Univ Lille 1 Sciences & Technologies Microemulsions aqueuses volatiles de parfums et d huiles essentielles basees sur l utilisation de solvo- surfactifs
WO2014090959A1 (en) * 2012-12-13 2014-06-19 Firmenich Sa Ethanol-free microemulsion perfuming compositions

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
J. I. GARCÍA ET AL: "Ecotoxicity studies of glycerol ethers in Vibrio fischeri : checking the environmental impact of glycerol-derived solvents", GREEN CHEMISTRY, vol. 17, no. 8, 1 January 2015 (2015-01-01), GB, pages 4326 - 4333, XP055416779, ISSN: 1463-9262, DOI: 10.1039/C5GC00857C *
JOSÉ I. GARCÍA ET AL: "Green solvents from glycerol. Synthesis and physico-chemical properties of alkyl glycerol ethers", GREEN CHEMISTRY, vol. 12, no. 3, 1 January 2010 (2010-01-01), pages 426, XP055025451, ISSN: 1463-9262, DOI: 10.1039/b923631g *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3669859A1 (en) * 2018-12-20 2020-06-24 Chanel Inc. Aqueous perfumes

Also Published As

Publication number Publication date
EP3630057A1 (fr) 2020-04-08
US20200179247A1 (en) 2020-06-11
FR3066913B1 (fr) 2019-07-26
JP2020521787A (ja) 2020-07-27
EP3630057B1 (fr) 2021-08-18
KR20200031565A (ko) 2020-03-24
FR3066913A1 (fr) 2018-12-07

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