FR3127119A1 - Use of fatty ester as fat-soluble UV filter solubilizing agent - Google Patents

Use of fatty ester as fat-soluble UV filter solubilizing agent Download PDF

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Publication number
FR3127119A1
FR3127119A1 FR2109777A FR2109777A FR3127119A1 FR 3127119 A1 FR3127119 A1 FR 3127119A1 FR 2109777 A FR2109777 A FR 2109777A FR 2109777 A FR2109777 A FR 2109777A FR 3127119 A1 FR3127119 A1 FR 3127119A1
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France
Prior art keywords
soluble
ester
fat
mono
use according
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.)
Pending
Application number
FR2109777A
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French (fr)
Inventor
Clémentine CHAMPAGNE
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.)
Arkema France SA
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Arkema France SA
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Publication date
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Priority to FR2109777A priority Critical patent/FR3127119A1/en
Priority to EP22790336.6A priority patent/EP4401702A1/en
Priority to PCT/FR2022/051724 priority patent/WO2023041869A1/en
Publication of FR3127119A1 publication Critical patent/FR3127119A1/en
Pending legal-status Critical Current

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    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • A61K2800/49—Solubiliser, Solubilising system

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Non-Alcoholic Beverages (AREA)
  • Fats And Perfumes (AREA)

Abstract

Utilisation d’ester gras en tant que solubilisant de filtre UV L’invention porte sur une utilisation d’un mono-ester de 2-octanol de formule suivante :R1-C(=O)OR2dans laquelle R1 désigne un groupe alkyle comprenant de 5 à 35 atomes de carbone etR2 désigne le 1-méthylheptyle,en tant qu’agent solubilisant de filtre UV liposoluble, le ratio massique du ou des filtres UV liposolubles sur le ou les mono-esters de 2-octanol étant compris entre 0,02 et 0,50.Use of a fatty ester as a UV filter solubilizer The invention relates to a use of a 2-octanol mono-ester of the following formula:R1-C(=O)OR2in which R1 denotes an alkyl group comprising from 5 with 35 carbon atoms andR2 denotes 1-methylheptyl, as a solubilizing agent for the fat-soluble UV filter, the mass ratio of the fat-soluble UV filter(s) to the 2-octanol mono-ester(s) being between 0.02 and 0.50.

Description

Utilisation d’ester gras en tant qu’agent solubilisant de filtre UV liposolubleUse of fatty ester as fat-soluble UV filter solubilizing agent

La présente invention concerne l’utilisation d’un mono-ester de 2-octanol en tant qu’agent solubilisant de filtre UV liposoluble.The present invention relates to the use of a 2-octanol mono-ester as a solubilizing agent for a fat-soluble UV filter.

Il est connu qu'un rayonnement de longueurs d'onde comprises entre 280 nm et 400 nm permet le bronzage de l'épiderme humain, tandis qu'un rayonnement de longueurs d'onde comprises entre 280 et 320 nm, appelés rayons UVB, nuit au développement d'un bronzage naturel. L'exposition à ces rayonnements est également susceptible d'entraîner un changement préjudiciable des propriétés biomécaniques de l'épiderme, se traduisant par l'apparition de rides conduisant à un vieillissement prématuré de la peau.It is known that radiation with wavelengths between 280 nm and 400 nm allows the human epidermis to be tanned, while radiation with wavelengths between 280 and 320 nm, called UVB rays, harms to the development of a natural tan. Exposure to this radiation is also likely to lead to a detrimental change in the biomechanical properties of the epidermis, resulting in the appearance of wrinkles leading to premature aging of the skin.

On sait également que les rayons UVA, dont la longueur d'onde est comprise entre 320 et 400 nm pénètrent plus profondément dans la peau que les rayons UVB. Les rayons UVA provoquent un brunissement immédiat et persistant de la peau. Une exposition quotidienne aux rayons UVA, même de courte durée, dans des conditions normales peut endommager les fibres de collagène et l’élastine, ce qui se traduit par une modification du microrelief de la peau, l’apparition de rides et une pigmentation inégale (taches, manque d'uniformité du teint).It is also known that UVA rays, whose wavelength is between 320 and 400 nm, penetrate deeper into the skin than UVB rays. UVA rays cause immediate and persistent darkening of the skin. Daily exposure to UVA rays, even of short duration, under normal conditions can damage collagen fibers and elastin, resulting in changes in the microrelief of the skin, the appearance of wrinkles and uneven pigmentation ( stains, uneven skin tone).

A ce jour, une grande diversité de compositions photoprotectrices sont déjà connues pour protéger les matières kératiniques, et plus particulièrement la peau, contre les effets néfastes induits par les rayonnements UVA et/ou UVB. Pour l’essentiel, elles contiennent une combinaison de plusieurs filtres UV organiques et/ou inorganiques à titre d’agent actif anti-UV, véhiculés en phase huileuse et/ou en phase aqueuse et sont généralement proposées sous une forme galénique de type brume, émulsion ou gel.To date, a wide variety of photoprotective compositions are already known for protecting keratin materials, and more particularly the skin, against the harmful effects induced by UVA and/or UVB radiation. Essentially, they contain a combination of several organic and/or inorganic UV filters as anti-UV active agent, conveyed in the oily phase and/or in the aqueous phase and are generally offered in a galenic form of the mist type, emulsion or gel.

Il est également connu que des forts taux de filtres sont nécessaires pour atteindre de hauts niveaux d’efficacité filtrante.It is also known that high filter rates are necessary to achieve high levels of filtering efficiency.

Or, des taux élevés en filtres UV ne se prêtent pas à une élaboration aisée de compositions dotées d’une texture stabilisée et agréable.However, high levels of UV filters do not lend themselves to easy preparation of compositions with a stabilized and pleasant texture.

L’un des premiers problèmes rencontrés porte sur la solubilisation de ces filtres. Des dispersions peuvent être observées. Or, une fois la composition appliquée sur la peau, la protection UV obtenue est totalement inhomogène.One of the first problems encountered relates to the solubilization of these filters. Dispersions can be observed. Now, once the composition has been applied to the skin, the UV protection obtained is completely inhomogeneous.

Ensuite, l’introduction de filtres UV à haute teneur provoque généralement des problèmes de déstabilisation de la composition. Une précipitation ou bien une cristallisation des filtres peut être observée. Dans le cas de compositions bi-phasiques, cette instabilité peut même parfois provoquer un déphasage de l’émulsion et/ou une perte de viscosité de la composition, rendant la formulation inefficace voire inutilisable.Then, the introduction of high-grade UV filters generally causes problems of destabilization of the composition. A precipitation or a crystallization of the filters can be observed. In the case of two-phase compositions, this instability can even sometimes cause a phase shift of the emulsion and/or a loss of viscosity of the composition, rendering the formulation ineffective or even unusable.

Ainsi, la qualité et la stabilité de la formulation ont un impact direct sur la protection UV attendue.Thus, the quality and stability of the formulation have a direct impact on the expected UV protection.

En conséquence, il existe un réel besoin de nouveaux solvants pour ces applications solaires, utilisant des composés complexes.Consequently, there is a real need for new solvents for these solar applications, using complex compounds.

La présente invention a pour but de proposer une nouvelle utilisation d’un solvant organique améliorant la solubilisation de filtres UV liposolubles, conduisant à des compositions stables et homogènes.The aim of the present invention is to propose a new use of an organic solvent improving the solubilization of fat-soluble UV filters, leading to stable and homogeneous compositions.

L’invention porte sur l’utilisation d’un mono-ester de 2-octanol de formule suivante :
R1-C(=O)OR2
dans laquelle
R1désigne un groupe alkyle comprenant de 5 à 35 atomes de carbone et
R2désigne le groupe 1-méthylheptyle,
en tant qu’agent solubilisant de filtres UV liposolubles,
le ratio massique du ou des filtres UV liposolubles sur le ou les mono-esters de 2-octanol étant compris entre 0,02 et 0,50.The invention relates to the use of a 2-octanol mono-ester of the following formula:
R 1 -C(=O)OR 2
in which
R 1 denotes an alkyl group comprising from 5 to 35 carbon atoms and
R 2 denotes the 1-methylheptyl group,
as a solubilizing agent for fat-soluble UV filters,
the mass ratio of the fat-soluble UV screening agent(s) to the 2-octanol mono-ester(s) being between 0.02 and 0.50.

Claims (10)

Utilisation d’un mono-ester de 2-octanol de formule suivante :
R1-C(=O)OR2
dans laquelle
R1désigne un groupe alkyle comprenant de 5 à 35 atomes de carbone et
R2désigne le 1-méthylheptyle,
en tant qu’agent solubilisant de filtre UV liposoluble,
le ratio massique du ou des filtres UV liposolubles sur le ou les mono-esters de 2-octanol étant compris entre 0,02 et 0,50.Use of a 2-octanol mono-ester of the following formula:
R 1 -C(=O)OR 2
in which
R 1 denotes an alkyl group comprising from 5 to 35 carbon atoms and
R 2 denotes 1-methylheptyl,
as a fat-soluble UV filter solubilizing agent,
the mass ratio of the fat-soluble UV screening agent(s) to the 2-octanol mono-ester(s) being between 0.02 and 0.50. Utilisation selon la revendication 1, caractérisée en ce que le groupe alkyle R1du mono-ester de 2-octanol comporte de 6 à 35 atomes de carbone, préférentiellement de 7 à 31 atomes de carbone, de préférence de 9 à 25 atomes de carbone, plus particulièrement de 11 à 23 atomes de carbone.Use according to claim 1, characterized in that the alkyl group R 1 of the 2-octanol mono-ester contains from 6 to 35 carbon atoms, preferably from 7 to 31 carbon atoms, preferably from 9 to 25 carbon atoms , more particularly from 11 to 23 carbon atoms. Utilisation selon la revendication 1 ou 2, caractérisée en ce que le mono-ester de 2-octanol est le palmitate de 1-méthylheptyle.Use according to Claim 1 or 2, characterized in that the 2-octanol mono-ester is 1-methylheptyl palmitate. Utilisation selon l’une quelconque des revendications précédentes, caractérisée en ce que le filtre UV liposoluble est choisi parmi l’avobenzone, éthylhexyltriazone, benzophenone-3, octocrylène, benzophenone-2, benzophénone-6, benzophénone-8, menthylanthranilate, éthylhexylsalicylate, 4-méthylbenzylidène camphor, octyl-N,N-diméthyl PABA, éthylhexyl diméthyl PABA, éthylhexyl méthoxycinnamate, isoamyl méthoxycinnamate, butyl méthoxydibenzoylméthane, diéthylamino hydroxybenzoyl hexyl benzoate, bis-éthylhexyloxyphénol méthoxyphényl triazine, drométrizole trisiloxane, méthylène bis-benzotriazolyl tétraméthylbutylphénol, diéthylhexyl butamido triazone, éthylhexyl triazone, isoamyl p-méthoxycinnamate, polysilicone-15, tris biphényl triazine, homomenthyl salicylate, et leur mélange.Use according to any one of the preceding claims, characterized in that the fat-soluble UV screening agent is chosen from avobenzone, ethylhexyltriazone, benzophenone-3, octocrylene, benzophenone-2, benzophenone-6, benzophenone-8, menthylanthranilate, ethylhexylsalicylate, 4 -methylbenzylidene camphor, octyl-N,N-dimethyl PABA, ethylhexyl dimethyl PABA, ethylhexyl methoxycinnamate, isoamyl methoxycinnamate, butyl methoxydibenzoylmethane, diethylamino hydroxybenzoyl hexyl benzoate, bis-ethylhexyloxyphenol methoxyphenyl triazine, drometrizole trisiloxane, methylene bis-benzotriazolyl tetramethylbutylphenol, diethylhexyl butamido tri azone, ethylhexyl triazone, isoamyl p-methoxycinnamate, polysilicone-15, tris biphenyl triazine, homomenthyl salicylate, and mixtures thereof. Utilisation selon l’une quelconque des revendications précédentes, caractérisée en ce que le ratio massique du ou des filtres UV liposolubles sur le ou les mono-esters de 2-octanol est compris entre 0,02 et 0,40, et plus particulièrement entre 0,03 et 0,30, et de manière encore plus préférée entre 0,04 et 0,20.Use according to any one of the preceding claims, characterized in that the mass ratio of the fat-soluble UV screening agent(s) to the 2-octanol mono-ester(s) is between 0.02 and 0.40, and more particularly between 0 0.03 and 0.30, and even more preferably between 0.04 and 0.20. Utilisation selon l’une quelconque des revendications précédentes, caractérisée en ce que le mono-ester est utilisé dans une composition solaire sous forme d’huile, d’émulsion huile dans l’eau ou eau dans l’huile.Use according to any one of the preceding claims, characterized in that the mono-ester is used in a sunscreen composition in the form of oil, oil-in-water or water-in-oil emulsion. Utilisation selon la revendication 6, caractérisée en ce que la composition solaire comporte en outre un ou plusieurs composants choisis parmi filtres UV hydrosolubles, filtres UV inorganiques, conservateurs, agents sensoriels, agents filmogènes, boosters de facteur de protection solaire, agents modificateurs de rhéologie, émulsionnants, émollients, humectants, parfums, colorants, pigments et principes actifs et leurs mélanges.Use according to Claim 6, characterized in that the sunscreen composition further comprises one or more components chosen from water-soluble UV filters, inorganic UV filters, preservatives, sensory agents, film-forming agents, sun protection factor boosters, rheology modifying agents, emulsifiers, emollients, humectants, perfumes, dyes, pigments and active ingredients and mixtures thereof. Composition solaire comportant au moins un filtre UV liposoluble, et au moins un mono-ester de 2-octanol, tel que défini dans l’une quelconque des revendications 1 à 3.Sun composition comprising at least one fat-soluble UV filter, and at least one 2-octanol mono-ester, as defined in any one of Claims 1 to 3. Composition selon la revendication 8, caractérisée en ce que le ratio massique du ou des filtres UV liposolubles sur le ou les mono-esters de 2-octanol est compris entre 0,02 et 0,40, et plus particulièrement entre 0,03 et 0,30, et de manière encore plus préférée entre 0,04 et 0,20.Composition according to Claim 8, characterized in that the mass ratio of the fat-soluble UV screening agent(s) to the 2-octanol mono-ester(s) is between 0.02 and 0.40, and more particularly between 0.03 and 0. .30, and even more preferably between 0.04 and 0.20. Composition solaire selon la revendication 8 ou 9, caractérisée en ce qu’elle comporte en outre un ou plusieurs composants choisis parmi filtres UV hydrosolubles, filtres UV inorganiques, conservateurs, agents sensoriels, agents filmogènes, boosters de facteur de protection solaire, agents modificateurs de rhéologie, émulsionnants, émollients, humectants, parfums, colorants, pigments et principes actifs et leurs mélanges.Sun composition according to Claim 8 or 9, characterized in that it additionally comprises one or more components chosen from water-soluble UV filters, inorganic UV filters, preservatives, sensory agents, film-forming agents, sun protection factor boosters, rheology, emulsifiers, emollients, humectants, perfumes, dyes, pigments and active ingredients and mixtures thereof.
FR2109777A 2021-09-17 2021-09-17 Use of fatty ester as fat-soluble UV filter solubilizing agent Pending FR3127119A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
FR2109777A FR3127119A1 (en) 2021-09-17 2021-09-17 Use of fatty ester as fat-soluble UV filter solubilizing agent
EP22790336.6A EP4401702A1 (en) 2021-09-17 2022-09-14 Use of fatty ester as a solubilising agent for fat-soluble uv filter
PCT/FR2022/051724 WO2023041869A1 (en) 2021-09-17 2022-09-14 Use of fatty ester as a solubilising agent for fat-soluble uv filter

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR2109777 2021-09-17
FR2109777A FR3127119A1 (en) 2021-09-17 2021-09-17 Use of fatty ester as fat-soluble UV filter solubilizing agent

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FR3127119A1 true FR3127119A1 (en) 2023-03-24

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016091930A1 (en) * 2014-12-09 2016-06-16 Basf Se Solubilizing agents for uv filters in cosmetic formulations
WO2018180009A1 (en) * 2017-03-30 2018-10-04 ビタミンＣ６０バイオリサーチ株式会社 Fullerene-containing cosmetic composition

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016091930A1 (en) * 2014-12-09 2016-06-16 Basf Se Solubilizing agents for uv filters in cosmetic formulations
WO2018180009A1 (en) * 2017-03-30 2018-10-04 ビタミンＣ６０バイオリサーチ株式会社 Fullerene-containing cosmetic composition

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DATABASE GNPD [online] MINTEL; 12 July 2018 (2018-07-12), ANONYMOUS: "High Protection Tanning Oil SPF 30", XP055917747, retrieved from https://www.gnpd.com/sinatra/recordpage/5825983/ Database accession no. 5825983 *
DATABASE GNPD [online] MINTEL; 2 May 2016 (2016-05-02), ANONYMOUS: "Perfect Protection Sunscreen SPF 50+/PA++++", XP055917740, retrieved from https://www.gnpd.com/sinatra/recordpage/4312773/ Database accession no. 4312773 *
DATABASE GNPD [online] MINTEL; 20 May 2013 (2013-05-20), ANONYMOUS: "Perfect Protection Sunscreen SPF 50+/PA+++", XP055918217, retrieved from https://www.gnpd.com/sinatra/recordpage/2129535/ Database accession no. 2129535 *

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Publication number Publication date
EP4401702A1 (en) 2024-07-24
WO2023041869A1 (en) 2023-03-23

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