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WO2025071660A1 - Composition de vernis à ongles contenant un composé pipéridinol - Google Patents

Composition de vernis à ongles contenant un composé pipéridinol Download PDF

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Publication number
WO2025071660A1
WO2025071660A1 PCT/US2024/015534 US2024015534W WO2025071660A1 WO 2025071660 A1 WO2025071660 A1 WO 2025071660A1 US 2024015534 W US2024015534 W US 2024015534W WO 2025071660 A1 WO2025071660 A1 WO 2025071660A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
nail
compositions
color
nail composition
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/US2024/015534
Other languages
English (en)
Inventor
Sam Morrison
Ramakrishnan Hariharan
I-Fan Hsieh
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 US18/478,091 external-priority patent/US20250107987A1/en
Priority claimed from FR2313885A external-priority patent/FR3156324A3/fr
Application filed by LOreal SA filed Critical LOreal SA
Publication of WO2025071660A1 publication Critical patent/WO2025071660A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00—Manicure or pedicure preparations
    • A61Q3/02—Nail coatings
    • 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
    • A61K8/34—Alcohols
    • 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
    • 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
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives

Definitions

  • No.8,454,940 relates to compositions containing stabilizing mixtures of (a) an effective stabilizing amount of at least one merocyanine derivative having an absorption maximum of 350 to 400 nm, (b) at least one UV filter selected from benzotriazole derivatives; and optionally (c) at least one excited state quencher; for the protection of body care and household products against the deleterious effects of light, heat and oxygen.
  • a) an effective stabilizing amount of at least one merocyanine derivative having an absorption maximum of 350 to 400 nm (b) at least one UV filter selected from benzotriazole derivatives; and optionally (c) at least one excited state quencher; for the protection of body care and household products against the deleterious effects of light, heat and oxygen.
  • some colorants found in nail polish such as red pigments are not particularly color stable against light and/or heat as well, which can result in changes in color intensity and/or color shade of the composition after exposure to light and/or heat.
  • the compositions contain little or no avobenzone, octocrylene, benzophenones, benzotriazoles and/or merocyanines.
  • the present invention also relates to methods of making nail compositions comprising combining at least one solvent, at least one coloring agent, at least one film forming agent, and at least one piperidinol compound during formation of the nail compositions.
  • at least one plasticizing agent is also added during formation of the nail compositions.
  • little or no UV filters are added during formation of the nail compositions.
  • the compositions contain little or no avobenzone, octocrylene, benzophenones, benzotriazoles and/or merocyanines.
  • UV filters and/or surfactants compositions of the invention which are “free of UV filters,” “substantially free of UV filters,” and “devoid of UV filters,” as well as “free of surfactants,” “substantially free of surfactants,” and “devoid of surfactants,” have meanings consistent with the discussion within this paragraph), even if not specifically discussed for each identified ingredient in the application. Discussed examples of the use of such language such as those in this paragraph are intended to be exemplary, not limiting.
  • “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.
  • FDA Food and Drug Administration
  • nail compositions comprising solvent, at least one coloring agent, at least one film forming agent, and at least one piperidinol compound are provided.
  • Solvent [0049] According to the present invention, nail compositions comprising at least one solvent are provided.
  • the at least one solvent is chosen from organic and inorganic solvents, which can be either volatile or non-volatile. Most preferably, the at least one solvent is at least one alkyl acetate.
  • the at least one solvent includes at least one C2-C8 monoalcohol.
  • suitable C2-C8 monoalchols include, but are not limited to, ethanol, propanol, butanol, isopropanol and isobutanol.
  • the nail compositions of the present invention are anhydrous.
  • the nail compositions of the present invention are free, substantially free, or devoid of water.
  • the nail compositions of the present invention are free, substantially free, or devoid of oil.
  • the nail compositions of the present invention are free, substantially free, or devoid of surfactant.
  • cellulose esters such as cellulose acetobutyrates or cellulose acetopropionates
  • cellulose alkylethers such as ethylcelluloses
  • ethylguars cellulose esters
  • Suitable film forming agents of natural origin also include plant resins such as dammars, elemi, copals, benzoin; gums such as shellac, sandarac and mastic. Atty.
  • Suitable acrylic polymers include polymers resulting from the copolymerization of monomers chosen from the esters and/or amides of acrylic acid and/or of methacrylic acid.
  • monomers of ester type mention may be made of methyl methacrylate, ethyl methacrylate, butyl methacrylate, isobutyl methacrylate, 2-ethylhexyl methacrylate and lauryl methacrylate.
  • monomers of amide type mention may be made of N-t-butylacrylamide and N-t- octylacrylamide.
  • Suitable acrylic polymers include polymers obtained by copolymerization of ethylenically unsaturated monomers containing hydrophilic groups, preferably of nonionic nature, such as hydroxyethyl acrylate, 2-hydroxypropyl acrylate, hydroxyethyl methacrylate and 2-hydroxypropyl methacrylate.
  • Suitable acrylic polymers also include styrene acrylate copolymers and acrylate silicone copolymers.
  • Piperidinol can also be substituted with non-hydroxyl group substitutions at one or more carbon positions on the ring, if desired, and up to two such substitutions can occur at each ring position, if desired.
  • Such additional non-hydroxyl group substitutions at one or more ring positions can include, but are not limited to, one or two substituted or unsubstituted, linear or branched, alkyl groups, preferably containing 1-8 carbon atoms, preferably 1-6 carbon atoms, preferably 1-3 carbon atoms, and preferably 1-2 carbon atoms.
  • Piperidinol can be in nonionic form, or in the form of a salt. Suitable salt forms of the piperidinol compound of the present invention include but are not Atty.
  • the at least one piperidinol compound has one hydroxy substitution.
  • the at least one piperidinol compound has at least one methyl substitution, preferably two to six methyl substitutions, and preferably 4 methyl substitutions. According to preferred embodiments, the 4 methyl substitutions occur at two positions on the ring.
  • nail compositions of the present invention may optionally further comprise at least one plasticizer.
  • plasticizers are additives used to optimize the mechanical properties of films. They tend to reduce the Glass Transition Temperature (Tg) and increase the softness and flexibility of the films.
  • suitable plasticizers have a boiling point measured at ambient pressure of less than or equal to 285° C., preferably less than or equal to 270° C., and preferably less than or equal to 250° C.
  • any plasticizing agent typically found in nail polish compositions can be used.
  • suitable plasticizers include, but are not limited to, glycols and their ester derivatives, esters of acids, in particular carboxylic acids, such as citrates, adipates, carbonates, tartrates, phosphates or sebacates, oxyethylenated derivatives, such as oxyethylenated oils, and their mixtures.
  • suitable plasticizing agents include, but are not limited to, diisobutyl adipate, the ester of tertbutyl acid and 2,2,4-trimethylpentane-1,3-diol, diethyl adipate, diethyl phthalate, dibutyl phthalate, dioctyl phthalate, butyl 2-ethylhexyl phthalate, dimethyl sebacate, dibutyl sebacate, ethyl stearate, 2-ethylhexyl palmitate, dipropylene glycol n-butyl ether, tributyl phosphate, tributoxyethyl phosphate, tricresyl phosphate, triphenyl phosphate, glycerol triacetate, butyl stearate, butyl glycolate, benzyl benzoate, butyl acetyltricinoleate, glyceryl acetyltricinole
  • the plasticizer is present in the nail compositions in an amount from about 0.1% to about 25% by weight, preferably from about 0.5% to about 20% by weight, preferably from about 1% to about 10% by weight, and preferably from about 3% to about 8% by weight, of the total weight of the composition, including all ranges and subranges there between.
  • the nail compositions of the present invention may also optionally further include at least one thixotropic.
  • the at least one thixotropic agent may be chosen, for example, from hydrophilic or organophilic clays, hydrophilic or hydrophobic fumed silicas, elastomeric organopolysiloxanes, and mixtures thereof.
  • Clays are silicates containing a cation that may be chosen from calcium, magnesium, aluminium, sodium, potassium, and lithium cations, and mixtures thereof.
  • hydrophilic clay means a clay that is capable of swelling in water; this clay swells in water and forms after hydration a colloidal dispersion.
  • examples of such products include, but are not limited to, clays of the smectite family such as montmorillonites, hectorites, bentonites, beidellites, and saponites, clays of the vermiculite family, stevensite, and chlorites.
  • These clays may be of natural or synthetic origin.
  • Non-limiting examples of hydrophilic clays include smectites such as saponites, hectorites, montmorillonites, bentonites, beidellite and, in at least one embodiment, synthetic hectorites (also known as laponites), for instance, the Atty.
  • the organophilic clays are clays modified with chemical compounds that make the clay capable of swelling in solvent media.
  • the clay may be chosen, for example, from montmorillonite, bentonite, hectorite, attapulgite, sepiolite, and mixtures thereof. In one embodiment, the clay is chosen from bentonite and hectorite.
  • the chemical compound used to modify the organophilic clay may be chosen, for instance, from quaternary amines, tertiary amines, amine acetates, imidazolines, amine soaps, fatty sulfates, alkyl aryl sulfonates, amine oxides, and mixtures thereof.
  • Suitable organophilic clays include, but are not limited to, stearalkonium clays such as stearalkonium hectorite and stearalkonium bentonites such as those sold under the names Bentone 27V by the company Elementis, Tixogel LG by the company United Catalyst, and Claytone AF and Claytone APA by the company Southern Clay; quaternium-18 bentonites such as those sold under the names Bentone 3, Bentone 38, Bentone 27 V CG, and Bentone 38V by the company Elementis, Tixogel VP by the company United Catalyst, and Claytone 34, Claytone 40, and Claytone XL by the company Southern Clay; and quaternium- Atty.
  • stearalkonium clays such as stearalkonium hectorite and stearalkonium bentonites such as those sold under the names Bentone 27V by the company Elementis, Tixogel LG by the company United Catalyst, and Claytone AF
  • hydrophilic fumed silicas may be obtained by high-temperature hydrolysis of a volatile silicon compound in an oxyhydric flame, producing a finely divided silica. Hydrophilic silicas have a large number of silanol groups at their surface.
  • hydrophilic silicas are sold, for example, under the names Aerosil 130®, Aerosil 200®, Aerosil 255®, Aerosil 300®, and Aerosil 380® by the company Degussa, and Cab-O-Sil HS-5®, Cab-O-Sil EH-5®, Cab-O-Sil LM-130®, Cab-O-Sil MS-55®, and Cab-O-Sil M-5® by the company Cabot.
  • the hydrophobic fumed silicas may be obtained by modification of the surface of the silica via a chemical reaction that generates a reduction in the number of silanol groups, these groups possibly being substituted, for example, with hydrophobic groups.
  • the hydrophobic groups may be chosen, for instance, from: [0122] trimethylsiloxyl groups, which may be obtained by treating fumed silica in the presence of hexamethyldisilazane.
  • Silicas thus treated are known as “Silica silylate” according to the CTFA (6th edition, 1995). They are sold, for example, under the references Aerosil R812® by the company Degussa, and Cab-O-Sil TS-530® by the company Cabot, [0123] dimethylsilyloxyl or polydimethylsiloxane groups, which may be obtained by treating fumed silica in the presence of polydimethylsiloxane or dimethyldichlorosilane.
  • Silicas thus treated are known as “Silica dimethyl silylate” according to the CTFA (6th edition, 1995). They are sold, for example, under the references Aerosil R972® and Aerosil R974® by the company Degussa, and Cab-O- Sil TS-610® and Cab-O-Sil TS-720® by the company Cabot. Atty.
  • the at least one thixotropic agent may be present in the composition in an amount from 0.05 percent by weight, for example, preferably ranging from about 0.05 percent to about 15 percent by weight, preferably from about 0.5 percent to about 10 percent by weight, and preferably from about 0.75 percent to about 5 percent by weight, relative to the total weight of the composition, including all ranges and subranges therebetween such as, for example 1% to 3%, 0.5% to 7%, 5% to 15%, etc.
  • Fillers [0126] According to preferred embodiments, the nail compositions of the present invention may also optionally further include at least one filler.
  • Suitable examples of fillers include mineral or organic particles of any shape, in sheet, spherical or oblong form, regardless of the crystallographic shape (for example sheet, cubic, hexagonal, orthorhombic, etc). Mention may be made of talc, mica, kaolin, polyamide (Nylon®) (Orgasol® from Atochem), poly- ⁇ -alanine and polyethylene powders, tetrafluoroethylene polymer powders (Teflon®), lauroyl-lysine, starch, boron nitride, acrylic acid copolymers (Polytrap® from Dow Corning) and silicone resin microbeads (Tospearls® from Toshiba, for example), elastomer polyorganosiloxane particles, precipitated calcium carbonate, magnesium carbonate and hydro-carbonate, hydroxyapatite, glass or ceramic microcapsules, metallic soaps derived from carboxylic organic acids having 8 to 22 carbon atoms, preferably from 12 to 18 carbon atom
  • the at least one filler is preferably present in an amount ranging from about 0.01% to about 15% by weight, preferably from about 0.1% to about 5% Atty. Docket: L1170432210US.1 (0397.1) OA23322-WO-PCT by weight, preferably from about 0.5% to about 2.5%, in relation to the total weight of the nail compositions, including all ranges and subranges therebetween.
  • Auxiliaries/Additives According to preferred embodiments, the compositions of the present invention may also optionally further include at least one additive or auxiliary commonly used in cosmetic compositions and known to a person skilled in the art as being capable of being incorporated into said compositions.
  • Such additives or auxiliaries may be chosen from preservatives, fragrances, oils, waxes, surfactants, antioxidants, agents for combating free radicals, spreading agents, wetting agents, dispersing agents, antifoaming agents, neutralizing agents, stabilizing agents, active principles chosen from essential oils, UV filters, moisturizing agents, vitamins, actives, proteins, ceramides, plant extracts, fibers, and the like, wetting agents and their mixtures.
  • nail compositions of the present invention are “free of,” “substantially free of,” or “devoid of” such additives.
  • composition of the invention 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 onto nails.
  • auxiliary additives may be present in the composition in a proportion from 0% to 99% (such as from 0.01% to 90%) relative to the total weight of the Atty.
  • the nail compositions of the present invention can be a basecoat (primer), a color coat or a topcoat (over coat).
  • each coat in the nail composition, itself, can comprise one or more layers.
  • the at least one color coat can comprise one or more color coat layers;
  • the at least topcoat can comprise one or more topcoat layers;
  • the at least one basecoat can comprise one or more basecoat layers.
  • each 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.
  • the basecoat (if present) is typically applied directly to the nail
  • the color coat is typically applied either directly to the nail (if no basecoat is present) or to a previously-applied basecoat
  • the topcoat (if present) is typically applied to a color coat.
  • methods of treating, protecting, enhancing the appearance of, caring for and/or making up nails by applying compositions of the present invention to the nails in an amount sufficient to treat, enhance the appearance of, care for and/or make up the nails are provided.
  • “making up” the nails includes applying at least one coloring agent to the nails in an amount sufficient to provide color and/or optical effect to the nails.
  • the compositions of the present invention are applied topically to the nails in an amount sufficient to treat, enhance the appearance of, care for and/or make up the nails.
  • the compositions may be applied to the desired area as needed, preferably once or twice Atty. Docket: L1170432210US.1 (0397.1) OA23322-WO-PCT 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.
  • methods of improving color intensity stability and/or color shade stability against light and/or heat of nail compositions comprising at least one solvent, at least one coloring agent, and at least one film forming agent are provided, wherein the methods comprise adding at least one piperidinol compound to the nail compositions during formation of the nail compositions in an amount sufficient to improve color stability of the nail compositions against light and/or heat.
  • the nail compositions further comprise at least one plasticizing agent.
  • the nail compositions contain little or no UV filters.

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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)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne des compositions pour les ongles contenant au moins un solvant, au moins un agent colorant, au moins un agent filmogène et au moins un composé pipéridinol, ainsi que des procédés de fabrication et d'utilisation de telles compositions.
PCT/US2024/015534 2023-09-29 2024-02-13 Composition de vernis à ongles contenant un composé pipéridinol Pending WO2025071660A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US18/478,091 US20250107987A1 (en) 2023-09-29 2023-09-29 Nail polish composition containing piperidinol compound
US18/478,091 2023-09-29
FRFR2313885 2023-12-11
FR2313885A FR3156324A3 (fr) 2023-12-11 2023-12-11 Composition de vernis a ongles contenant un composé pipéridinol

Publications (1)

Publication Number Publication Date
WO2025071660A1 true WO2025071660A1 (fr) 2025-04-03

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2024/015534 Pending WO2025071660A1 (fr) 2023-09-29 2024-02-13 Composition de vernis à ongles contenant un composé pipéridinol

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Country Link
WO (1) WO2025071660A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5001175A (en) 1989-04-11 1991-03-19 Estron Chemical, Inc. Epoxy-sulfonamide compounds and compositions
US6939551B2 (en) 2001-05-21 2005-09-06 Coty Inc. Cosmetic films
US8454940B2 (en) 2007-08-24 2013-06-04 Basf Se Mixtures comprising benzotriazoles and merocyanines
US20140093460A1 (en) * 2012-10-02 2014-04-03 Amy Doan Nail enamel composition
US8790669B2 (en) 2011-09-30 2014-07-29 L'oreal Cosmetic compositions comprising latex film formers
CN105919831A (zh) * 2016-06-22 2016-09-07 上海零玖科技有限公司 一种免擦洗光固化甲油胶
BE1025011B1 (nl) * 2017-08-28 2018-09-20 Professionails N.V. Samenstelling voor het aanbrengen van een kunstnagel en/of nagelcoating

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5001175A (en) 1989-04-11 1991-03-19 Estron Chemical, Inc. Epoxy-sulfonamide compounds and compositions
US6939551B2 (en) 2001-05-21 2005-09-06 Coty Inc. Cosmetic films
US8454940B2 (en) 2007-08-24 2013-06-04 Basf Se Mixtures comprising benzotriazoles and merocyanines
US8790669B2 (en) 2011-09-30 2014-07-29 L'oreal Cosmetic compositions comprising latex film formers
US20140093460A1 (en) * 2012-10-02 2014-04-03 Amy Doan Nail enamel composition
CN105919831A (zh) * 2016-06-22 2016-09-07 上海零玖科技有限公司 一种免擦洗光固化甲油胶
BE1025011B1 (nl) * 2017-08-28 2018-09-20 Professionails N.V. Samenstelling voor het aanbrengen van een kunstnagel en/of nagelcoating

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
ANONYMOUS: "CIBA TINOSAN SDC", INTERNET CITATION, 1 October 2009 (2009-10-01), pages 1 - 50, XP002548625, Retrieved from the Internet <URL:http://www.ciba.com/ext-hpc-new2007q4prestsdc20070919.pdf?wobj=62680> [retrieved on 20091001] *
DATABASE GNPD [online] MINTEL; 1 December 2015 (2015-12-01), ANONYMOUS: "Nail Colour", XP093173983, retrieved from https://www.gnpd.com/sinatra/recordpage/3646011/ Database accession no. 3646011 *
DATABASE GNPD [online] MINTEL; 26 November 2014 (2014-11-26), ANONYMOUS: "Nail Colour", XP093173776, retrieved from https://www.gnpd.com/sinatra/recordpage/2791887/ Database accession no. 2791887 *
DATABASE GNPD [online] MINTEL; 8 December 2017 (2017-12-08), ANONYMOUS: "Nail BB Gel", XP093173770, retrieved from https://www.gnpd.com/sinatra/recordpage/5305727/ Database accession no. 5305727 *

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