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WO2025137031A1 - Compositions contenant de la bis-éthylhexyloxyphénol méthoxyphényl triazine et un système antioxydant - Google Patents

Compositions contenant de la bis-éthylhexyloxyphénol méthoxyphényl triazine et un système antioxydant Download PDF

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Publication number
WO2025137031A1
WO2025137031A1 PCT/US2024/060658 US2024060658W WO2025137031A1 WO 2025137031 A1 WO2025137031 A1 WO 2025137031A1 US 2024060658 W US2024060658 W US 2024060658W WO 2025137031 A1 WO2025137031 A1 WO 2025137031A1
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WO
WIPO (PCT)
Prior art keywords
composition
compositions
weight
antioxidant system
present disclosure
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
PCT/US2024/060658
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English (en)
Inventor
Sang Lee BANG
Brian Bodnar
Martin Josso
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.)
LOreal SA
Original Assignee
LOreal SA
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
Priority claimed from US18/543,921 external-priority patent/US20250195377A1/en
Priority claimed from FR2403282A external-priority patent/FR3160578A3/fr
Application filed by LOreal SA filed Critical LOreal SA
Publication of WO2025137031A1 publication Critical patent/WO2025137031A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4966—Triazines or their condensed derivatives
    • 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
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • 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
    • A61K8/67—Vitamins
    • A61K8/676—Ascorbic acid, i.e. vitamin C
    • 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
    • A61K8/67—Vitamins
    • A61K8/678—Tocopherol, i.e. vitamin E
    • 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
    • A61K2800/20—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
    • A61K2800/31—Anhydrous

Definitions

  • compositions comprising 2,4-bis- ⁇ [4- (2-ethyl hexyloxy) -2-hydroxy] -phenyl ⁇ -6- (4-methoxyphenyl) -1,3,5-triazine (INCI name: bis-ethylhexyloxyphenol methoxyphenyl triazine) and an antioxidant system, as well as to methods of making and using such compositions.
  • UVB rays Radiation of wavelengths between 290 nm and 400 nm allows tanning of the human epidermis, while radiation of wavelengths between 290 and 320 nm, called UVB rays, hinders the development of a natural tan. Exposure 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 (i.e. photoaging). Docket No.: L1170432420WO (0413.7) [0004] UVA rays with wavelengths between 320 and 400 nm penetrate deeper into the skin than UVB rays. UVA rays cause immediate and persistent browning of the skin.
  • antioxidants it is advantageous to add antioxidants to products designed to be applied to keratinous material, particularly the skin, for their ability to neutralize free radicals and Reactive Oxygen Species (ROS) generated under Oxidative Stress.
  • Oxidative Stress can be initiated by many extrinsic factors, including UV light.
  • antioxidants in combination with UV filters into sun care compositions to attempt to reduce the effect of oxidative stress resulting from exposure to UV light.
  • UVA light is particularly implicated in the ability to generate ROS and oxidative Stress, which can be particularly problematic for skin and can lead to skin damage.
  • antioxidants are not particularly stable against light, breaking down after exposure to light, which can result in less antioxidant activity being Docket No.: L1170432420WO (0413.7) available over time in a composition which ultimately would result in lower amounts of compounds in need of antioxidant protection available in the composition to effect their desired or intended functionality.
  • L1170432420WO (0413.7) available over time in a composition which ultimately would result in lower amounts of compounds in need of antioxidant protection available in the composition to effect their desired or intended functionality.
  • one aspect of the present disclosure is a composition which possesses good antioxidant stability against light in addition to possessing good UV protection properties.
  • compositions comprising an antioxidant system and bis-ethylhexyloxyphenol methoxyphenyl triazine (BEMT or bemotrizinol).
  • BEMT bis-ethylhexyloxyphenol methoxyphenyl triazine
  • the bis-ethylhexyloxyphenol methoxyphenyl triazine (BEMT) is present in the compositions in an amount effective to improve antioxidant system photostability against light.
  • the present disclosure also relates to methods of treating, caring for, protecting, enhancing the appearance of, and/or making up a keratinous material comprising applying compositions of the present disclosure to a keratinous material in an amount sufficient to treat, care for, enhance the appearance of, and/or make up the keratinous material.
  • the present disclosure also relates to methods of improving antioxidant system stability, in particular photostability, in compositions comprising an antioxidant system, wherein the methods comprise adding bis-ethylhexyloxyphenol methoxyphenyl triazine to the compositions during formation of the compositions in an Docket No.: L1170432420WO (0413.7) amount sufficient to improve stability, in particular photostability, of the antioxidant system.
  • the present disclosure also relates to methods of making compositions comprising combining bis-ethylhexyloxyphenol methoxyphenyl triazine and an antioxidant system in the compositions during formation of the compositions.
  • the bis-ethylhexyloxyphenol methoxyphenyl triazine (BEMT) is added to the compositions in an amount effective to improve stability, in particular photostability, of the antioxidant system.
  • the present disclosure also relates to methods of improving antioxidant system stability against light of compositions comprising an antioxidant system, wherein the methods comprise adding bis-ethylhexyloxyphenol methoxyphenyl triazine (BEMT) to the compositions during formation of the compositions in an amount sufficient to improve antioxidant system stability in the compositions against light.
  • BEMT bis-ethylhexyloxyphenol methoxyphenyl triazine
  • “About” as used herein means within 10% of the indicated number (e.g., “about 10%” means 9% – 11% and “about 2%” means 1.8% - 2.2%).
  • “A” or “an” as used herein means “at least one.” Docket No.: L1170432420WO (0413.7)
  • “At least one” means one or more and thus includes individual components as well as mixtures/combinations.
  • all ranges provided are meant to include every specific point and range within, and combination of subranges between, the given ranges.
  • a range from 1-5 includes specifically the integers within the range 1, 2, 3, 4 and 5, as well as subranges such as and 2-5, 3-5, 2-3, 2-4, 1-4, etc., as well as all fractional numbers within the range such as 1.2, 2.3, 3.4, etc., and subranges including such fractional numbers such as 1.5-3.8, 2-4.3, 4.2-4.9, etc.
  • “Film former”, “film-forming polymer” or “film-forming agent” as used herein means a polymer or resin which is capable of leaving a film on the substrate to which it is applied, for example, after a solvent accompanying the film former has evaporated, absorbed into and/ or dissipated on the substrate.
  • “Substituted” as used herein, means comprising at least one substituent.
  • substituents include atoms, such as hydrogen atoms or chlorine atoms, as well as functional groups, such as hydroxyl groups, ether groups, alkoxy groups, acyloxyalky groups, oxyalkylene groups, polyoxyalkylene groups, carboxylic acid groups, amine groups, acylamino groups, amide groups, halogen containing groups, ester groups, thiol groups, sulphonate groups, thiosulphate groups, siloxane groups, and polysiloxane groups.
  • the substituent(s) may be further substituted.
  • Volatile as used herein, means having a flash point of less than about 115°C.
  • Non-volatile as used herein, means having a flash point of greater than about 115°C. Docket No.: L1170432420WO (0413.7)
  • Polymer as used herein means a compound which is made up of at least two monomers.
  • Free or “substantially free” or “devoid of” as it is used herein means that while it is preferred that no amount of the specific component be present in the composition, it is possible to have very small amounts of it in the compositions of the disclosure provided that these amounts do not materially affect at least one, preferably most, of the advantageous properties of the compositions of the disclosure.
  • free of oil means that an effective amount (that is, more than trace amounts) of oil(s) is/are omitted from the composition (that is, about 0% by weight), “substantially free of oil” means that oil(s) is/are present in amounts not greater than 0.1% by weight, and “devoid of oil” means that oil(s) is/are present in amounts not greater than 0.25% by weight, based on the total weight of the composition.
  • UV filters as it is used herein means sunscreen active agents approved by a governmental regulatory agency such as the Food and Drug Administration (FDA) in the U.S. or the EU Commission in Europe and includes Docket No.: L1170432420WO (0413.7) organic UV filters such as avobenzone, octocrylene, benzophenones, benzotriazoles and merocyanines, as well as mineral UV filters such as zinc oxide (ZnO) and titanium dioxide (TiO2).
  • FDA Food and Drug Administration
  • “Physiologically acceptable” means compatible with keratinous materials and having a pleasant color, odor and feel, and which does not cause any unacceptable discomfort (stinging or tautness) liable to discourage a consumer from using the composition.
  • “UV protection efficiency” or “filtering efficiency” in the context of the present disclosure is evaluated from one or more of SPF, UVAPF, Critical Wavelength, and UVA-I/UV ratio.
  • SPF Stress Protection Factor
  • compositions of the present disclosure comprise 10% or less by weight relative to the total weight of composition of additional UV filters, preferably less than 5% by weight relative to the total weight of composition, preferably less than 3% by weight relative to the total weight of composition, and preferably less than 1% by weight relative to the total weight of composition.
  • compositions of the present disclosure comprise 10% or less by weight relative to the total weight of composition of additional organic UV filters, preferably less than 5% by weight relative to the total weight of composition, preferably less than 3% by weight relative to the total weight of composition, and preferably less than 1% by weight relative to the total weight of composition.
  • the composition comprises at least one non-volatile oil.
  • non-volatile oils that may be used in the present disclosure include, but are not limited to, polar oils such as, for example: [0121] - - esters and ethers, in particular fatty acids, such as oils of formulas R1COOR2, wherein R 1 represents the remainder of a fatty acid having from 8 to 29 carbon atoms, and R 2 represents a hydrocarbon chain, branched or not, containing from 3 to 30 carbon atoms, such as for example Purcellin oil, isononyl isononanoate, isopropyl myristate, ethyl-2-hexyl palmitate, octyl-2-dodecyl stearate, octyl-2-dodecyl erucate, isostearyl isostearate;
  • non-volatile oils examples include, but are not limited to, non-polar oils such as branched and unbranched hydrocarbons, in particular Vaseline (petrolatum), paraffin oil, squalane, squalene, hydrogenated polyisobutene, hydrogenated polydecene, polybutene, mineral oil, pentahydrosqualene, and mixtures thereof. Docket No.: L1170432420WO (0413.7) [0128] According to certain embodiments of the present disclosure, the compositions of the present disclosure comprise at least one non-volatile silicone oil.
  • Suitable examples of such silicone oils include, but are not limited to, non-volatile silicone fluids such as, for example, polyalkyl (aryl) siloxanes.
  • Suitable polyalkyl siloxanes include, but are not limited to, polydimethyl siloxanes, which have the CTFA designation dimethicone, polydiethyl siloxane, phenyl trimethicone, trimethyl pentaphenyl trisiloxane, phenyldimethicone, phenyltrimethylsiloxydiphenylsiloxane, diphenyldimethicone, and diphenylmethyldiphenyltrisiloxane and those siloxanes disclosed in U.S.
  • Suitable high viscosity silicone oils include, but are not limited to, 15 M 30 from PCR (500 cSt) or Belsil PDM 1000 (1000 cSt) from Wacker and Dow Corning 200 (350 cSt) (the values in parenthesis represent viscosities at 25 ⁇ C).
  • Particularly preferred oils include, but are not limited to, one or more of the following: Diisopropyl Sebacate, C12-15 Alkyl Benzoate, Phenethyl Benzoate, Isopropyl Lauroyl Sarcosinate, Diisopropyl Adipate, Dibutyl Adipate, Dicaprylyl Carbonate, Dicaprylate/Dicaprate, Coco Glycerides, Caprylic/capric triglyceride, Isopropyl Myristat, Isopropyl Palmitate, Coco Caprylate/Caprate, Ethylhexyl Palmitate, Isononyl isononanoate, Octyl dodecanol, Isohexadecane, isododecane, Dicaprylyl Ether, C15-19 Alkane, and mxtures thereof.
  • compositions of the present disclosure are devoid of water, substantially free of water, or free of water as defined herein.
  • the compositions of the present disclosure are anhydrous.
  • the aqueous phase may comprise at least one water-soluble organic solvent which is liquid at room temperature and atmospheric pressure.
  • such at least one water- soluble organic solvent may include: [0134] Triethyl citrate; Docket No.: L1170432420WO (0413.7) [0135] C1-C5 monoalcohols having a C1-C5 alkane chain and a single hydroxyl function (OH).
  • Suitable C1-C5 monoalcohols include methanol, ethanol, propanol, isopropanol, butanol and mixtures thereof; [0136] polyols (compounds having 2 or more hydroxyl groups) having, for example from 2 to 20 carbon atoms, preferably from 2 to 6 carbon atoms, such as for example glycerol, diglycerol, propylene glycol, isoprene glycol, dipropylene glycol, butylene glycol, hexylene glycol, 1,3-propanediol, pentylene glycol, simple sugars, and water-soluble polyalkylene glycols; [0137] and mixtures thereof.
  • polyols compounds having 2 or more hydroxyl groups having, for example from 2 to 20 carbon atoms, preferably from 2 to 6 carbon atoms, such as for example glycerol, diglycerol, propylene glycol, isoprene glycol, dipropylene glycol,
  • compositions of the present disclosure are “free of,” “substantially free of,” or “devoid of” such additives.
  • an example of a commercially-available product of such a piperidinol compound is Tinogard® Q available from BASF, which contains 10% active agent, and/or SPF boosters.
  • composition of the disclosure should be cosmetically or dermatologically acceptable, i.e., it should contain a non-toxic physiologically acceptable.
  • the composition may be in any galenic form normally employed in the cosmetic and dermatological fields which is suitable for topical administration as discussed above.
  • compositions of the present disclosure can be a stand-alone product (for use by itself), or they can be a product for use in conjunction with another composition, for example it can be a basecoat (primer) composition, a color coat composition, or a topcoat (over coat) composition.
  • compositions of the present disclosure when applied to keratinous materials in the form of any of such compositions, such application can comprise one or more layers of the product.
  • application of at least one color coat composition can comprise one or more color coat layers
  • application of the at least topcoat composition can comprise one or more topcoat layers
  • application of the at least one basecoat composition can comprise one or more basecoat layers.
  • basecoat, color coat and topcoat compositions contain three or fewer layers of compositions, preferably two or fewer layers of compositions, and preferably a single layer of compositions.
  • compositions of the present disclosure are typically applied directly to keratinous material, color coat is typically applied either directly to the keratinous material (if no basecoat is present) or to a previously-applied basecoat, and topcoat (if present) is typically applied to a color coat.
  • methods of treating, protecting, enhancing the appearance of, caring for and/or making up keratinous material by applying compositions of the present disclosure to the keratinous material in an amount sufficient to treat, enhance the appearance of, care for and/or make up the keratinous material are provided.
  • “treating” keratinous material includes applying a composition comprising an antioxidant system to the keratinous material in an amount sufficient to provide treatment effect to the keratinous material such as, for example, decreasing the appearance of fine lines and/or wrinkles, decreasing the appearance of discoloration (e.g., age spots), increasing smoothness, increasing moisturization, decreasing free radical formation, etc.
  • “protecting” keratinous material includes applying a composition of the present disclosure to the keratinous material in an amount sufficient to protect the keratinous material from damage resulting from exposure to UV rays.
  • compositions of the present disclosure are applied topically to the keratinous material in an amount sufficient to treat, enhance the appearance of, care for and/or make up the keratinous material.
  • the compositions may be applied to the desired area as needed, preferably once or twice daily, more preferably once daily and then preferably allowed to dry before subjecting to contact such as with clothing or other objects (for example, clothes or a topcoat).
  • the composition is allowed to dry for about 1 minute or less, more preferably for about 45 seconds or less.
  • compositions comprising an antioxidant system
  • methods of improving antioxidant system stability, in particular photostability, in compositions comprising an antioxidant system comprising adding bis-ethylhexyloxyphenol methoxyphenyl triazine to the compositions during formation of the compositions in an amount sufficient to improve stability, in particular photostability, of the antioxidant system.
  • Docket No.: L1170432420WO (0413.7) [0152]
  • methods of making compositions comprising combining bis-ethylhexyloxyphenol methoxyphenyl triazine and an antioxidant system in the compositions during formation of the compositions.
  • the bis-ethylhexyloxyphenol methoxyphenyl triazine (BEMT) is added to the compositions in an amount effective to improve stability, in particular photostability, of the antioxidant system.
  • the methods comprise adding bis-ethylhexyloxyphenol methoxyphenyl triazine (BEMT) to the compositions during formation of the compositions in an amount sufficient to improve antioxidant system stability in the compositions against light.
  • kits and/or prepackaged materials suitable for consumer use containing one or more compositions according to the description herein, alone or in combination with other consumer care products such as makeup products such as basecoats, topcoats, removal compositions, etc.
  • the packaging and application device for any subject of the disclosure may be chosen and manufactured by persons skilled in the art on the basis of their general knowledge, and adapted according to the nature of the composition to be packaged. Indeed, the type of device to be used can be in particular linked to the consistency of the composition, in particular to its viscosity; it can also depend on the nature of the constituents present in the composition, such as the presence of volatile compounds.
  • compositions comprising bemotrizinol and an antioxidant system, wherein the bemotrizinol is present in the composition in an amount effective to improve antioxidant system stability; [0157] The composition of the preceding embodiment, wherein the composition comprises 10% or less by weight relative to the total weight of composition of additional UV filters; [0158] The composition of any preceding embodiment, wherein the composition comprises less than 1.25% by weight relative to the total weight of composition of the antioxidant system, preferably than 1% by weight relative to the total weight of composition of the antioxidant system; [0159] The composition of any preceding embodiment, wherein the composition comprises 10% or less by weight relative to the total weight of composition of additional organic UV filters; [0160] The composition of any preceding embodiment, wherein the composition is anhydrous or in the form of an emulsion; [0161] The composition of any preceding embodiment, in the form of a stick.
  • composition of any preceding embodiment further comprising at least one coloring agent
  • composition of any preceding embodiment further comprising at least one active agent
  • a method of improving antioxidant system stability in a composition comprising an antioxidant system comprising adding bis-ethylhexyloxyphenol methoxyphenyl triazine to the composition during formation of the composition in an amount sufficient to improve stability of the antioxidant system.

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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)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne des compositions comprenant de la 2,4-bis-{[4-(2-éthyl hexyloxy)-2-hydroxy]-phényl}-6-(4-méthoxyphényl)-1,3,5-triazine et un système antioxydant, ainsi que des procédés de fabrication et d'utilisation de telles compositions.
PCT/US2024/060658 2023-12-18 2024-12-18 Compositions contenant de la bis-éthylhexyloxyphénol méthoxyphényl triazine et un système antioxydant Pending WO2025137031A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US18/543,921 2023-12-18
US18/543,921 US20250195377A1 (en) 2023-12-18 2023-12-18 Compositions containing bis-ethylhexyloxyphenol methoxyphenyl triazine and antioxidant system
FRFR2403282 2024-03-29
FR2403282A FR3160578A3 (fr) 2024-03-29 2024-03-29 Compositions contenant de la bis-ethylhexyloxyphenol methoxyphenyl triazine et systeme antioxydant

Publications (1)

Publication Number Publication Date
WO2025137031A1 true WO2025137031A1 (fr) 2025-06-26

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