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WO2025006850A1 - Compositions d'émulsion e/h contenant un composé pullulane modifié de manière hydrophobe et un agent de formation de film en phase aqueuse - Google Patents

Compositions d'émulsion e/h contenant un composé pullulane modifié de manière hydrophobe et un agent de formation de film en phase aqueuse Download PDF

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Publication number
WO2025006850A1
WO2025006850A1 PCT/US2024/035974 US2024035974W WO2025006850A1 WO 2025006850 A1 WO2025006850 A1 WO 2025006850A1 US 2024035974 W US2024035974 W US 2024035974W WO 2025006850 A1 WO2025006850 A1 WO 2025006850A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
oil
compound
present
water
Prior art date
Application number
PCT/US2024/035974
Other languages
English (en)
Inventor
Brady ZARKET
Yixin Yang
Original Assignee
L'oreal
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 US18/345,499 external-priority patent/US20250000760A1/en
Priority claimed from FR2311122A external-priority patent/FR3154002A3/fr
Application filed by L'oreal filed Critical L'oreal
Publication of WO2025006850A1 publication Critical patent/WO2025006850A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • 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
    • A61K8/064—Water-in-oil emulsions, e.g. Water-in-silicone emulsions
    • 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
    • A61K8/31—Hydrocarbons
    • 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
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon compounds
    • 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
    • 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
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8176—Homopolymers of N-vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • 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
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers

Definitions

  • the present invention relates to water-in-oil (w/o) emulsions (compositions) comprising at least one hydrophobically-modified pullulan compound and at least one aqueous phase film former, as well as to methods and kits comprising such emulsion compositions in container(s) or in application.
  • the compositions have beneficial cosmetic properties including good or improved wear, water and/or sebum resistance, and/or transfer resistance properties, in particular sebum resistance.
  • DISCUSSION OF THE BACKGROUND [0003] At the present time on the market for caring for and making up keratin materials, many products claim staying power throughout the day, withstanding external factors such as water, sebum, mechanical friction, etc.
  • compositions comprising unmodified silicone resin as film forming agent are known, such as the compound having the INCI name: Trimethylsiloxysilicate or a compound having the INCI name: Polypropylsilsesquioxane, or alternatively a silicone acrylate copolymer such as the product having the INCI name: Acrylates/polytrimethylsiloxymethacrylate copolymer).
  • unmodified silicone resin such as the compound having the INCI name: Trimethylsiloxysilicate or a compound having the INCI name: Polypropylsilsesquioxane, or alternatively a silicone acrylate copolymer such as the product having the INCI name: Acrylates/polytrimethylsiloxymethacrylate copolymer).
  • the aim of the present invention is to propose compositions which offer excellent staying power of the expected cosmetic effects, notably the color of the makeup on keratin materials (skin, lips, nails, hair, eyelashes, eyebrows) which may extend the duration of the cosmetic composition on keratin materials, as well as improve wear of the cosmetic composition on keratin materials and its resistance to external forces such as one or more of mechanical friction, water, sweat and perspiration, sebum, oil, etc.
  • the aim of the present invention is to propose compositions which afford staying power of the expected cosmetic effects, notably the color of the makeup on keratin materials, combined with a good level of comfort in comparison with conventional systems, in particular based on unmodified silicone resin.
  • volatile silicone oils examples include linear or cyclic silicone oils having a viscosity at room temperature less than or equal to 6 cSt and having from 2 to 7 silicon atoms, these silicones being optionally substituted with alkyl or alkoxy groups of 1 to 10 carbon atoms.
  • Specific oils that may be used in the invention include octamethyltetrasiloxane, decamethylcyclopentasiloxane, 19 WBD (US) 4857-1748-0140v1 Atty. Dkt.
  • the oil carrier comprises one or more non-silicone volatile oils and may be selected from volatile hydrocarbon oils, volatile esters and volatile ethers.
  • volatile non-silicone oils include, but are not limited to, volatile hydrocarbon oils having from 8 to 16 carbon atoms and their mixtures and in particular branched C8 to C16 alkanes such as C8 to C16 isoalkanes (also known as isoparaffins), isododecane, isodecane, and for example, the oils sold under the trade names of Isopar or Permethyl.
  • the low HLB surfactant comprises a backbone and pendant group(s), wherein (1) the backbone is hydrophobic and one or more pendant groups is/are hydrophilic, or (2) the backbone is hydrophilic and one or more pendant groups is/are hydrophobic.
  • the backbone can be silicone-based or hydrocarbon based.
  • backbone it is meant that the surfactant comprises a main chain.
  • pendant group(s), it is meant that one or more groups is attached to the backbone or main chain of the surfactant.
  • the pendant group(s) can be silicone-based or hydrocarbon based, and can be attached at any location along the backbone or main chain, for example at one or both terminal ends of the chain, at location(s) not at a terminal end of the chain, or both. According to preferred embodiments, the pendant group(s) include one or more ester group(s) attached to the backbone or main chain.
  • a preferred backbone is a hydrophobic such as, for example, one or more C8-C24 fatty compounds, preferably C12-C20 fatty compound(s), and preferably C16-C18 fatty compound(s) such as, for example, stearate, isostearate, laurate, etc, and a preferred pendant group 24 WBD (US) 4857-1748-0140v1 Atty. Dkt. L1170431860WO (0186.3) OA23217-WO-PCT for such a backbone is a hydrophilic group such as a polyethylene glycol (PEG) polymer or a polyglyceryl polymer.
  • PEG polyethylene glycol
  • Suitable emulsifiers include alkoxylated compounds, partial glycerides of alkoxylated compounds, polyglycerolated compounds, and mixtures thereof, etc. Polyglycerolated compounds are preferred. [00111] Suitable polyglycerolated compounds include, but are not limited to, compounds preferably containing 2 to 20 glyceryl groups, preferably 3 to 15 glyceryl groups, and preferably 4 to 10 glyceryl groups. Polyglyceryl-4 Diisostearate/Polyhydroxystearate/Sebacate, sold under the tradename Isolan GPS by Evonik, is particularly preferred. 25 WBD (US) 4857-1748-0140v1 Atty. Dkt.
  • compositions further comprising at least one thickening agent are provided.
  • Clays that may especially be mentioned include kaolinite, 27 WBD (US) 4857-1748-0140v1 Atty. Dkt. L1170431860WO (0186.3) OA23217-WO-PCT montmorillonites, saponites, laponites, hectorites, and illites. Mixtures of clays and natural clays may also be used.
  • Natural clays that may be mentioned include green clays, in particular rich in illite; clays rich in montmorillonite, known as fuller's earth, or such as bentonite or else white clays rich in kaolinite.
  • the thickening agent(s) is/are present in the compositions of the present invention in amounts ranging from about 0.1 to about 30% by weight, preferably from 0.5 to 25% by weight, preferably from 1 to 20% and preferably from 2.5 to 15% by weight, all weights based on the weight of the composition as a whole, including all 28 WBD (US) 4857-1748-0140v1 Atty. Dkt. L1170431860WO (0186.3) OA23217-WO-PCT ranges and subranges therebetween such as, for example, 0.1 to 1.5%, 2 to 20%, 10 to 20%, etc.
  • compositions further comprising at least one active agent are provided.
  • the active agent is in the aqueous phase (hydrophilic active agent), although active agents may be present in the oil phase (hydrophobic active agent).
  • the active agent may be: [00132] a moisturizing agent, such as a polyol such as, for example, glycerin and sugars, urea and its derivatives, such as in particular hydroxyalkyl urea, in particular hydroxyalkylurea, and mixtures thereof; [00133] a desquamating agent, which may be a compound capable of acting either directly on desquamation by promoting exfoliation, such as ⁇ -hydroxy acids, in particular salicylic acid and its derivatives (including 5-n-octanoylsalicylic acid); ⁇ -hydroxy acids, such as glycolic acid, citric acid, lactic acid, tartaric acid, malic acid or mandelic acid; urea; gentisic acid; oligofucoses; cinnamic acid; extract of Saphora japonica; resveratrol and certain jasmonic acid derivatives; or acting on the enzymes involved in the desquamation or degradation of
  • a moisturizing agent
  • agents for chelating mineral salts EDTA; N-acyl-N,N′,N′-ethylenediaminetriacetic acid; aminosulfonic compounds and in particular (N-2-hydroxyethylpiperazine-N- 2-ethane)sulfonic acid (HEPES); 2-oxothiazolidine-4-carboxylic acid 29 WBD (US) 4857-1748-0140v1 Atty. Dkt.
  • OA23217-WO-PCT procysteine derivatives
  • ⁇ -amino acid derivatives of the type such as glycine (as described in EP-0852949 and sodium methylglycinediacetate sold by BASF under the trade name Trilon M); honey; sugar derivatives such as O-octanoyl-6-D-maltose and N-acetylglucosamine; [00134] a humectant;
  • an anti-aging agent which may include, for example, one or more of C-beta-D-xylopyranoside-2-hydroxypropane (Pro-Xylane), retinol, peptides, caffeine, and other components that provide improvement to skin texture, any other suitable soluble/dispersible targeted active ingredient, and combinations thereof.
  • a mattifying agent which may include, but is not limited to, mattifying fillers such as, for example, talc, silica, silicone elastomers, and polyamides, and waxes such as, for example, beeswax and copernicia cerifera (carnauba) wax.
  • a pigment modifying agent and/or skin lightening agents such as double-stranded RNA oligonucleotides are useful for decreasing tyrosinase expression.
  • the composition of the invention should be cosmetically or dermatologically acceptable, i.e., it should contain a non- toxic physiologically acceptable medium and should be able to be applied to the skin of human beings.
  • methods of treating, caring for and/or enhancing the appearance of skin by applying compositions of the present invention to the skin in an amount sufficient to treat, care for and/or enhance the appearance of the skin are provided.
  • the compositions of the present invention are applied topically to the desired area of the skin in an amount sufficient to treat, care for and/or enhance the appearance of the skin.
  • 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, a topcoat).
  • the composition is 33 WBD (US) 4857-1748-0140v1 Atty. Dkt. L1170431860WO (0186.3) OA23217-WO-PCT allowed to dry for about 1 minute or less, more preferably for about 45 seconds or less.
  • the composition is preferably applied to the desired area that is dry or has been dried prior to application, or to which a basecoat has been previously applied.
  • Example 1 Sample W/O Emulsion Foundation Formulation 37 WBD (US) 4857-1748-0140v1 Atty. Dkt. L1170431860WO (0186.3) OA23217-WO-PCT [00168]
  • Example 2 Exemplified W/O Emulsion Foundations [00169]
  • Example 3 Comparison of 60o gloss values for oil- phase and combined oil-phase + water-phase film former foundations.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dispersion Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des compositions d'émulsion eau dans huile (E/H), de préférence pour le maquillage de la peau, comprenant au moins un composé pullulane modifié de manière hydrophobe et au moins un agent filmogène aqueux, ainsi que des procédés comprenant de telles compositions d'émulsion dans l'application.
PCT/US2024/035974 2023-06-30 2024-06-28 Compositions d'émulsion e/h contenant un composé pullulane modifié de manière hydrophobe et un agent de formation de film en phase aqueuse WO2025006850A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US18/345,499 US20250000760A1 (en) 2023-06-30 2023-06-30 Emulsion compositions containing pullulan compound and acrylamide film former
US18/345,499 2023-06-30
FRFR2311122 2023-10-16
FR2311122A FR3154002A3 (fr) 2023-10-16 2023-10-16 Compositions d’émulsion contenant un composé pullulane hydrophobiquement modifié et un filmogène en phase aqueuse

Publications (1)

Publication Number Publication Date
WO2025006850A1 true WO2025006850A1 (fr) 2025-01-02

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2024/035974 WO2025006850A1 (fr) 2023-06-30 2024-06-28 Compositions d'émulsion e/h contenant un composé pullulane modifié de manière hydrophobe et un agent de formation de film en phase aqueuse

Country Status (1)

Country Link
WO (1) WO2025006850A1 (fr)

Citations (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2311122A1 (fr) 1975-05-14 1976-12-10 Bentley Eng Co Ltd Mecanismes a encliquetage destines notamment a equiper un metier circulaire de bonneterie
WO1993018743A1 (fr) 1992-03-20 1993-09-30 Janssen Pharmaceutica N.V. Agent de regulation de l'etat graisseux de la peau
JPH08208989A (ja) 1994-12-01 1996-08-13 Shin Etsu Chem Co Ltd シリコーンオイル組成物
EP0852949A2 (fr) 1997-03-31 1998-07-15 Shiseido Company Limited Utilisation des alpha-aminoacides pour favoriser la dégradation des desmosomes ou la desquamation du stratum corneum
JP2001278729A (ja) * 2000-03-28 2001-10-10 Shiseido Co Ltd 油中水型乳化組成物
US6338839B1 (en) 1998-08-10 2002-01-15 L'oreal Transfer-resistant make-up or care composition containing a volatile linear silicone
US20030082221A1 (en) 2001-09-27 2003-05-01 Lavipharm Laboratories Inc. Pullulan based film forming cosmetic compositions
WO2003042221A1 (fr) 2001-11-13 2003-05-22 Ge Bayer Silicones Gmbh & Co. Kg Utilisation de siloxanes comme supports evaporables
US20040170586A1 (en) 2002-06-12 2004-09-02 L'oreal Cosmetic composition containing a polyorganosiloxane polymer
JP2005325088A (ja) * 2004-05-17 2005-11-24 Shiseido Co Ltd 皮膚外用剤
EP1604632B1 (fr) * 2004-06-08 2007-06-06 Shiseido Co., Ltd. Composition cosmétique comprenant un terpolymère spécifique
US20160113860A1 (en) 2013-05-09 2016-04-28 Shin-Etsu Chemical Co., Ltd. Oil-based thickening agent, oil-based thickening composition, and cosmetic preparation
EP3308767A1 (fr) * 2015-06-10 2018-04-18 Shin-Etsu Chemical Co., Ltd. Produit cosmétique
US20200022898A1 (en) 2017-06-30 2020-01-23 Coty Inc. Film forming compositions and uses thereof
WO2020104502A1 (fr) * 2018-11-20 2020-05-28 L V M H Recherche Composition cosmétique de maquillage à effet perfecteur longue tenue
CN111801092A (zh) 2019-02-01 2020-10-20 株式会社资生堂 浸渗用油包水型乳化化妆料
US11033478B2 (en) 2017-11-29 2021-06-15 L'oreal Mascara compositions comprising a polymer having cyclic amide, cyclic amine and acrylamide functionality
FR3104958A1 (fr) 2019-12-19 2021-06-25 L V M H Recherche Fond de Teint ultra-haute tenue
FR3110849A1 (fr) 2020-05-28 2021-12-03 L V M H Recherche Composition cosmétique eyeliner
US11253462B2 (en) 2017-12-15 2022-02-22 Lvmh Recherche Cosmetic composition comprising a pullulan derivative
WO2022135682A1 (fr) * 2020-12-21 2022-06-30 Lvmh Recherche Composition cosmétique eau-dans-huile

Patent Citations (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2311122A1 (fr) 1975-05-14 1976-12-10 Bentley Eng Co Ltd Mecanismes a encliquetage destines notamment a equiper un metier circulaire de bonneterie
WO1993018743A1 (fr) 1992-03-20 1993-09-30 Janssen Pharmaceutica N.V. Agent de regulation de l'etat graisseux de la peau
JPH08208989A (ja) 1994-12-01 1996-08-13 Shin Etsu Chem Co Ltd シリコーンオイル組成物
EP0852949A2 (fr) 1997-03-31 1998-07-15 Shiseido Company Limited Utilisation des alpha-aminoacides pour favoriser la dégradation des desmosomes ou la desquamation du stratum corneum
US6338839B1 (en) 1998-08-10 2002-01-15 L'oreal Transfer-resistant make-up or care composition containing a volatile linear silicone
JP2001278729A (ja) * 2000-03-28 2001-10-10 Shiseido Co Ltd 油中水型乳化組成物
US20030082221A1 (en) 2001-09-27 2003-05-01 Lavipharm Laboratories Inc. Pullulan based film forming cosmetic compositions
WO2003042221A1 (fr) 2001-11-13 2003-05-22 Ge Bayer Silicones Gmbh & Co. Kg Utilisation de siloxanes comme supports evaporables
US20040170586A1 (en) 2002-06-12 2004-09-02 L'oreal Cosmetic composition containing a polyorganosiloxane polymer
JP2005325088A (ja) * 2004-05-17 2005-11-24 Shiseido Co Ltd 皮膚外用剤
EP1604632B1 (fr) * 2004-06-08 2007-06-06 Shiseido Co., Ltd. Composition cosmétique comprenant un terpolymère spécifique
US20160113860A1 (en) 2013-05-09 2016-04-28 Shin-Etsu Chemical Co., Ltd. Oil-based thickening agent, oil-based thickening composition, and cosmetic preparation
EP3308767A1 (fr) * 2015-06-10 2018-04-18 Shin-Etsu Chemical Co., Ltd. Produit cosmétique
US20200022898A1 (en) 2017-06-30 2020-01-23 Coty Inc. Film forming compositions and uses thereof
US11033478B2 (en) 2017-11-29 2021-06-15 L'oreal Mascara compositions comprising a polymer having cyclic amide, cyclic amine and acrylamide functionality
US11253462B2 (en) 2017-12-15 2022-02-22 Lvmh Recherche Cosmetic composition comprising a pullulan derivative
WO2020104502A1 (fr) * 2018-11-20 2020-05-28 L V M H Recherche Composition cosmétique de maquillage à effet perfecteur longue tenue
CN111801092A (zh) 2019-02-01 2020-10-20 株式会社资生堂 浸渗用油包水型乳化化妆料
FR3104958A1 (fr) 2019-12-19 2021-06-25 L V M H Recherche Fond de Teint ultra-haute tenue
FR3110849A1 (fr) 2020-05-28 2021-12-03 L V M H Recherche Composition cosmétique eyeliner
WO2022135682A1 (fr) * 2020-12-21 2022-06-30 Lvmh Recherche Composition cosmétique eau-dans-huile

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
"International Cosmetic Ingredient Dictionary and Handbook", 2002
S. CAILLÈRES. HÉNINM. RAUTUREAU: "Clay Mineralogy", 1982, article "Mineralogie des argiles"

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