WO2018220147A1 - Parfums sous forme de microémulsions aqueuses - Google Patents
Parfums sous forme de microémulsions aqueuses Download PDFInfo
- 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
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
- A61K8/068—Microemulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/10—General cosmetic use
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/26—Optical properties
- A61K2800/262—Transparent; Translucent
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/30—Characterized by the absence of a particular group of ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/59—Mixtures
- A61K2800/596—Mixtures 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)
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 |
Family
ID=59859199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2018/064389 Ceased WO2018220147A1 (fr) | 2017-06-01 | 2018-05-31 | Parfums sous forme de microémulsions aqueuses |
Country Status (6)
| Country | Link |
|---|---|
| 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)
| 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)
| 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)
| 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 |
-
2017
- 2017-06-01 FR FR1754850A patent/FR3066913B1/fr not_active Expired - Fee Related
-
2018
- 2018-05-31 JP JP2019566073A patent/JP2020521787A/ja not_active Withdrawn
- 2018-05-31 WO PCT/EP2018/064389 patent/WO2018220147A1/fr not_active Ceased
- 2018-05-31 KR KR1020197036592A patent/KR20200031565A/ko not_active Ceased
- 2018-05-31 EP EP18730991.9A patent/EP3630057B1/fr active Active
- 2018-05-31 US US16/618,195 patent/US20200179247A1/en not_active Abandoned
Patent Citations (4)
| 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)
| 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)
| 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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