WO2023212375A1 - Compositions comprenant un polyphénol et un composé non ionique y - Google Patents

Compositions comprenant un polyphénol et un composé non ionique y Download PDF

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Publication number
WO2023212375A1
WO2023212375A1 PCT/US2023/020491 US2023020491W WO2023212375A1 WO 2023212375 A1 WO2023212375 A1 WO 2023212375A1 US 2023020491 W US2023020491 W US 2023020491W WO 2023212375 A1 WO2023212375 A1 WO 2023212375A1
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Prior art keywords
composition
compound
compositions
present
weight
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PCT/US2023/020491
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English (en)
Inventor
Brady ZARKET
Anne-Laure Suzanne BERNARD
Yixin Yang
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L'oreal
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Priority claimed from US17/731,815 external-priority patent/US20230346653A1/en
Priority claimed from US17/731,809 external-priority patent/US20230346681A1/en
Priority claimed from US17/731,802 external-priority patent/US20230346658A1/en
Priority claimed from FR2206831A external-priority patent/FR3137567A1/fr
Priority claimed from FR2206835A external-priority patent/FR3137568A1/fr
Priority claimed from FR2206832A external-priority patent/FR3137571A1/fr
Application filed by L'oreal filed Critical L'oreal
Publication of WO2023212375A1 publication Critical patent/WO2023212375A1/fr

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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
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • 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
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • 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
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • 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
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06—Lipsticks
    • 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
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • 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
    • A61Q1/08—Preparations containing skin colorants, e.g. pigments for cheeks, e.g. rouge
    • 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
    • A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara

Definitions

  • compositions in particular foundation compositions for cosmetics, comprising (1) at least one polyphenol X comprising at least two different phenol groups; (2) at least one nonionic compound Y, as well as to methods of using said compositions.
  • 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 from one day, including makeup removal at the end of the day, to staying power over several days, which is resistant to mechanical friction, water, sweat and perspiration, sebum, oil, cleansing products such as shower gels, shampoos, two-phase products and certain micellar waters.
  • keratin materials skin, lips, nails, hair, eyelashes, eyebrows
  • cleansing products such as shower gels, shampoos, two-phase products and certain micellar waters.
  • one aspect of the present invention is a composition, in particular a foundation composition, which has improved properties with respect to composition ease and/or comfort of application of the composition, composition stability, and/or composition color stability, and in particular with respect to improved properties related to the presence of polyphenols such as tannic acid in the compositions including properties such as improved stability and/or water resistance.
  • the present invention relates to compositions, in particular foundation compositions for cosmetics, comprising a solvent system.
  • the solvent system comprises water and the water is present in an amount of at least about 10% by weight with respect to the total weight of the composition.
  • the solvent system further comprises at least one C2-C5 monoalcohol in an amount effective to inhibit formation of a precipitate of compound X and compound Y in the composition prior to application.
  • the compositions further comprise at least one poly oxy alky lenated nonionic compound Y preferably having about four to about seven oxyalkylene units per molecule and optionally with a molar mass greater than 200 g/mol. Additionally, the compositions comprise at least one pigment.
  • the polyoxyalkylenated nonionic compound Y has an HLB above about 7.
  • the at least one C2-C5 monoalcohol is present in the composition in a concentration by weight of about 55% by weight or less.
  • the at least one at least one C2-C5 monoalcohol e.g., ethanol
  • the at least one at least one C2-C5 monoalcohol is or includes ethanol.
  • the at least one C2-C5 monoalcohol (e.g., ethanol) is present in a concentration by weight in the composition from about 5% to about 55%
  • the water is present in a concentration by weight in the composition from 10% to about 40%
  • compound X and compound Y are each independently present in a concentration by weight from about 0.5% to about 25%
  • the at least one C2-C5 monoalcohol is present in a concentration such that a weight ratio of (C2- C5 monoalcohol) to (C2-C5 monoalcohol plus water) is present in a weight ratio of at least about 0.3.
  • the present invention also relates to compositions, in particular foundation compositions for cosmetics, comprising a solvent system.
  • the solvent system comprises water and the water is present in an amount of at least about 10% by weight with respect to the total weight of the composition.
  • the solvent system further comprises at least one C2-C5 monoalcohol in an amount effective to inhibit formation of a precipitate of compound X and compound Y in the composition prior to application.
  • the compositions further comprise at least one glycerolated nonionic compound Y optionally with a molar mass greater than 200 g/mol.
  • the compositions comprise at least one pigment.
  • the glycerolated nomomc compound Y has an HLB above 7.
  • the at least one C2-C5 monoalcohol is present in the composition in a concentration by weight of about 55% by weight or less. In certain embodiments, the at least one at least one C2-C5 monoalcohol (e.g., ethanol) may be present in a concentration by weight in the composition ranging from about 5% to about 55%. In certain embodiments, the at least one at least one C2-C5 monoalcohol is or includes ethanol.
  • the at least one C2-C5 monoalcohol (e.g., ethanol) is present in a concentration by weight in the composition from about 5% to about 55%
  • the water is present in a concentration by weight in the composition from 10% to about 40%
  • compound X and compound Y are each independently present in a concentration by weight from about 0.5% to about 25%
  • the at least one C2-C5 monoalcohol is present in a concentration such that a weight ratio of (C2- C5 monoalcohol) to (C2-C5 monoalcohol plus water) is present in a weight ratio of at least about 0.3.
  • the present invention further relates to compositions, in particular emulsion compositions for cosmetics, comprising water.
  • the water is present in an amount of at least about 5% by weight with respect to the total weight of the composition.
  • the compositions further comprise at least one polyphenol X comprising at least two phenol groups.
  • the compositions further comprise at least one polyoxyalkylenated and/or glycerolated nonionic compound Y, optionally with a molar mass greater than 200 g/mol.
  • the at least one polyoxyalkylenated and/or glycerolated nonionic compound Y preferably has an HLB less than about 8.
  • the compositions comprise at least one pigment.
  • compound X is tannic acid.
  • compound Y has an HLB value less than six.
  • the composition system optionally comprises at least one C2-C5 monoalcohol such as ethanol that, if present, is present in the composition in a concentration by weight of less than about 50% by weight.
  • nonionic compound Y has an HLB value less than six, the water is present in a concentration by weight in the composition from 5% to about 70%, compound X and compound Y are each independently present in a concentration by weight from about 0.5% to about 25%, and the emulsion composition meets one or more of the following properties: has a shear modulus, G’ at 0.1% strain of at least about 150 Pa or has a yield stress of at least 7 Pa.
  • the present invention also relates to methods of caring for, and/or making up, and/or priming for caring for and/or making up keratinous material by applying compositions of the present invention to the keratinous material in an amount sufficient to care for, and/or to make up, and/or to prime for caring for and/or making up the keratinous material.
  • “About” as used herein means within 15% of the indicated number (e.g. “about I5%” means 8.5% - 11.5% and “about 2%” means 1.7% - 2.3%), such as within 10% of the indicated number, such as within 5% of the indicated number.
  • At least one means one or more and thus includes individual components as well as mixtures/combinati ons .
  • ranges provided are meant to include every specific range within, and combination of subranges between, the given ranges.
  • a range from 1-5 includes specifically 1, 2, 3, 4 and 5, as well as subranges such as and 2-5, 3-5, 2-3, 2-4, 1-4, etc.
  • Ranges in the form of, for example, “from about 0.5%, 1%, or 2% to about 4%, 5%, or 15%, ” also specifically contemplate from about 0.5% to about 4%, from about 0.5% to about 5%, 0.5% to about 15%, from about 1% to about 4%, from about 1% to about 5%, 1% to about 15%, from about 2% to about 4%, from about 2% to about 5%, and 2% to about 15%.
  • Film former means a polymer or resin that leaves 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.
  • Additional film former refer to film formers other than compound X and compound Y, which are capable of forming a film upon removal of the C2-C5 monoalcohol.
  • “Wax” as used herein is a lipophilic fatty compound that is solid at ambient temperature (25°C) and changes from the solid to the liquid state reversibly, having a melting temperature of more than 30°C and, for example, more than 45°C, and a hardness of more than 0.5 MPa at ambient temperature.
  • “Substituted” as used herein, means comprising at least one substituent.
  • Non-limiting examples of substituents include atoms, such as oxygen atoms and nitrogen 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, arnrde 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 100°C.
  • Non-volatile means having a flash point of greater than about 100°C.
  • Poly mer as used herein means a compound which is made up of at least two monomers.
  • Polymer as used herein means a compound which is made up of at least two monomers.
  • free of triethanolamine (TEA) means that an effective amount (that is, more than trace amounts) of TEA is omitted from the composition
  • substantially free of TEA means that TEA is are present in amounts not greater than 0.
  • compositions of the invention which are “free of oils,” “substantially free of oils,” and “devoid of oils” have meanings consistent with the discussion within this paragraph), even if not specifically discussed for each identified ingredient. Discussed examples of the use of such language are intended to be exemplary, not limiting.
  • “Makeup Result” refers to compositions where color remains the same or substantially the same as at the time of application, as viewed by the naked eye, after an extended period of time. “Makeup Result” may be evaluated by evaluating long wear properties by any method known in the art for evaluating such properties. For example, long wear may be evaluated by a test involving the application of a composition to keratin materials such as lips and evaluating the color of the composition after an extended period of time. For example, the color of a composition may be evaluated immediately following application to keratin materials such as lips and these characteristics may then be re-evaluated and compared after a certain amount of time. Further, these characteristics may be evaluated with respect to other compositions, such as commercially available compositions.
  • Keratinous material or “keratin material” means natural nails, lips, skin such as the face, the body, the hands, and the area around the eyes, and keratin fibres such as head hair, eyelashes, eyebrows, bodily hair of a human, as well as synthetic additions such as false eyelashes, false eyebrows, false nails, etc.
  • “Phy siologically acceptable” means compatible with keratinous material 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.
  • Acceptable pH levels for compositions of the present invention are preferably slightly or somewhat acidic, that is, less than 7, preferably 6.5 or less, preferably 6.0 or less, preferably 5.5 or less, including all ranges and subranges therebetween such as, for example 3 to 5, 4 to 6, 3 to 4.5, etc.
  • compositions of the present invention may also be in the form of a gel composition.
  • Gel composition means a composition which does not flow similar to a liquid when applied to a substrate, a composition which has a 3 -dimensional network that inhibits the composition from spreading on, or dripping from, a substrate after application owing to gravity.
  • G' storage modulus
  • G" loss modulus
  • G' storage modulus
  • G" loss modulus
  • the gel may have a gel crossover point at >0.1% strain, preferably >1% strain, and preferably less than 200% strain, preferably less than 150% strain.
  • Gel Crossover Point (Sol/Gel Point), means the point at which the G" (loss modulus) intersects the G' (storage modulus), reported in % strain. It is the point at which a composition goes from a more solid state to a more liquid state.
  • An example of a method for determining gel crossover point is as follows: G" (loss modulus) and G' (storage modulus) using a Discovery HR- 3 Rheometer by TA Instruments, having 40 mm 2° cone-and-plate stainless steel geometry. The test can be run @ 25°C, with test parameter of angular frequency of 1.0 rad/s and logarithmic sweep: Strain % 0.01 to 100.0% or 1000.0% with 10 points per decade. Results reported in % strain.
  • “Hydrogen bonding interaction” means an interaction involving a hydrogen atom of one of the two reagents and an electronegative heteroatom of the other reagent, such as oxygen, nitrogen, sulfur and fluorine.
  • the hydrogen bonding forms between the hydroxyl functions (OH) of the reactive phenol groups of the polyphenol X and the reactive hydroxyl groups of the compound Y, which are capable of forming hydrogen bonding with those of said phenol groups of the polyphenol X.
  • Coating agent formed by interaction by hydrogen bonds of at least one polyphenol X comprising at least two different phenol groups with the compound Y means that the conditions are met so that the reaction can be carried out between the two reagents, in particular that : i) the amount of polyphenol X is sufficient in the composition containing it, and ii) the compound Y is soluble, miscible or solubilized by another solvent in the medium of the composition containing it, and iii) the compound Y has a sufficient number of hydrogen bond acceptor groups to react with the phenol groups of polyphenol X and, in the medium of the composition containing it, and iv) the compound Y, in the medium of the composition containing it, does not comprise in its structure any group which does not allow the formation of hydrogen bonding with the functions of the reactive phenol groups of the polyphenol X, such as for example, one or more anionic group.
  • “Natural compound” refers to any compound derived directly from a natural substance such as a
  • Compound of natural origin refers to any compound derived from a natural compound which has undergone one or more chemical modifications, for example by organic synthesis reaction, without the properties of the natural compound having been modified.
  • Synthetic compound refers to any compound which is not a natural compound or a compound of natural origin.
  • Root temperature means 25°C.
  • “Atmospheric pressure” means 760 mmHg, i.e. 10 5 pascals.
  • Coating agent refers to any compound which is capable of forming a deposit on the surface of a keratin material to which it has been applied.
  • Haldrogen bonding-inhibiting agent refers to any compound which is capable of preventing hydrogen bonding interaction between the polyphenol X and the compound Y and/or which is capable of dissociating the complex formed by said interaction by breaking the hydrogen bonding.
  • compositions and methods of the present invention can comprise, consist of, or consist essentially of the essential elements and limitations of the invention descnbed herein, as well as any additional or optional ingredients, components, or limitations described herein or otherwise useful.
  • the surfactant component of the composition can “consist essentially of’ identified surfactant(s) or types of surfactants discussed below.
  • compositions, components and methods which “consist essentially of’ identified ingredients or actions is either “prevention of precipitation or chemical associations generated by compound X and compound Y prior to use” or, if the composition is an emulsion composition, “building viscosity, yield stress or shear modulus.”
  • compositions comprising at least one polyphenol X comprising at least two different phenol groups are provided.
  • the polyphenols X that may be used according to the present invention include in their structure at least two different phenol groups.
  • polyphenol refers to any compound containing in its chemical structure at least two and preferably at least three phenol groups.
  • phenol group refers to any group comprising an aromatic ring, preferably a benzene ring, including at least one hydroxyl group (OH).
  • the polyphenols X that may be used according to the invention may be synthetic or natural. They may be in isolated form or contained in a mixture, notably contained in a plant extract. Polyphenols are phenols comprising at least two phenol groups that are differently substituted on the aromatic ring.
  • the two classes of polyphenols are flavonoids and non-flavonoids.
  • flavonoids examples include chaicones such as phloretin, phloridzin, aspalathin or neohesperidin; flavanols such as catechin, fisetin, kaempferol, myricetin, quercetin, rutin, procyanidins, proanthocyanidins, pyroanthocyanidins, theaflavins or thearubigins (or thearubrins); dihydroflavonols such as astilbin, dihydroquercetin (taxifolin) or silibinin; flavanones such as hesperidin, neohesperidin, hesperetin, naringenin or naringin; anthocyanins such as cyanidin, delphinidin, malvidin, peonidin or petunidin; catechin tannins such as tannic acid; isoflavonoids such as
  • non-flavonoids examples include curcuminoids such as curcumin or tetrahydrocurcumin; stilbenoids such as astringin, resveratrol or rhaponticin; aurones such as aureusidin; and mixtures thereof.
  • polyphenols that may be used according to the invention, mention may also be made of chlorogenic acid, verbascoside; coumarins substituted with phenols.
  • the polyphenol X will be chosen from catechin tannins such as gallotannins chosen from tannic acid; ellagitannins such as epigallocatechin, epigallocatechin gallate, castalagin, vescalagin, vescalin, castalin, casuarictin, castanopsinins, excoecarianins, grandinin, notn, roburins, pterocarinin, acutissimin, tellimagrandins, sanguiin, potentillin, pedunculagin, geraniin, chebulagic acid, repandisinic acid, ascorgeraniin, stachyurin, casuarinin, casuariin, punicacortein, coriariin, cameliatannin, isodeshy drodigalloyl, dehydrodigalloyl, hellinoyl, punicalagin and r
  • the polyphenol X is epigallocatechin, in particular a green tea extract having the INCI name Green Tea Extract, notably comprising at least 45% epigallocatechin relative to the total weight of said extract, for instance the commercial product sold under the name Dermofeel Phenon 90 M-C® sold by the company Evonik Nutrition & Care or the commercial product sold under the name Tea Polyphenols Green Tea Extract® by the company Tayo Green Power.
  • the polyphenol X is a procyanidin or a mixture of procyanidins, in particular an extract of maritime pine bark having the INCI name Pinus pinaster Bark/Bud Extract, notably comprising at least 65% by weight of procyanidins relative to the total weight of said extract, such as the commercial product sold under the name Pycnogenol® sold by the company Bio prises Aromes.
  • Tannic acid will be used more particularly as polyphenol X.
  • the polyphenol(s) X according to the invention is preferably present in a content equal or greater than 0.5% by weight, such as from about 0.5%, 0.75% 1 %, 1 .5% or 2% to about 2.5%, 4%, 5%, 10%, 15%, 20% 25% or 30% - all percentages by weight relative to the total weight of the composition containing it (them).
  • Nonionic Compound Y is preferably present in a content equal or greater than 0.5% by weight, such as from about 0.5%, 0.75% 1 %, 1 .5% or 2% to about 2.5%, 4%, 5%, 10%, 15%, 20% 25% or 30% - all percentages by weight relative to the total weight of the composition containing it (them).
  • compositions comprising at least one glycerolated and/or polyoxyalkylenated nonionic compound Y are provided.
  • compound Y has a molar mass greater than 200 g/mol. In one preferred embodiment, the molar mass of the compound Y is greater than 350 g/mol.
  • the compound Y is surface active (i.e., is a surfactant) and may be capable of depressing surface tension of deionized water when placed in such deionized water at a surfactant concentration of 0.25% by weight at room temperature and pressure to less than about 60 mN/m, such as less than about 50 mN/m, such as less than about 40 mN/m.
  • nonionic compound it is meant a compound that does not ionize in water.
  • polyoxyalkylenated compound refers to any molecule comprising in its chemical structure at least chain comprising oxyalkylene units, in particular oxy ethylene units - (OCH2CH2)n and/or oxypropylene units - (OCFhCFhCFDp, where n and p are 2 or greater.
  • the term “glycerolated compound” refers to any molecule comprising in its chemical structure a glycerol group or a chain comprising glycerol units -(O-CH2-CHOH-CH2)m.
  • the compound Y is a polyglycerolated compound, meaning any molecule comprising in its chemical structure a glycerol group or a chain comprising glycerol units -(O-CFh-CHOH-CFF)TM, where m is 2 or greater.
  • PG is used as an abbreviation of poly glycerol or polyglyceryl.
  • Glycerolated alkyl ethers such as glyceryl lauryl ether
  • Glycerol or poly glycerol esters of fatty acids which are optionally polyhydroxylated, such as polyglyceryl-3 polyncinoleate, polyglyceryl-2 dhsostearate, polyglyceryl-4 dnsostearate, polyglyceryl-2 stearate, polyglyceryl-3 diisostearate, polyglyceryl-2 triisostearate, glyceryl stearate citrate and polyglyceryl-2 dipolyhydroxystearate,
  • Polyoxyethylenated or polyglycerolated waxes notably chosen from polyoxy ethylenated ester waxes such as PEG-8 Beeswax, and Polyglyceryl-3 Beeswax,
  • nonionic compound Y can be a “polyoxyalkylenated compound” which refers to any molecule comprising in its chemical structure at least chain comprising oxy alkylene units, in particular oxy ethylene units - (OCH2CH2)n and/or oxypropylene units - (OCH 2 CH 2 CH2)p, where n or p are, on average from 4 to 7.
  • a polyoxyalkylenated Nonionic Compound Y may also optionally be glycerolated.
  • polyoxyethylenated alkylglycerides such as PEG-6 Caprylic/Capric Glycerides (PEG-6 “CCG,” herein), PEG-7 Caprylic/capric glycerides (PEG-7 “CCG,” herein), and PEG-7 Glyceryl cocoate.
  • the polyoxyalkylenated compound may be, for example polyethylene glycols of the type H(O-CH 2 -CH 2 )n-OH; poloxamers of the type HO-(CH2-CH2-O)n-(CHCH 3 -CH 2 -O)O-(CH 2 - CH2-O)p-H; polypropylene glycol alkyl ethers of the type:
  • Polyoxyethylenated butters in particular polyoxyethylenated shea butter,
  • Nonionic Compound Y is selected from a polyoxyalkenated compound having from about 4 to about 7 (e.g., from 4 to 7) oxy ethylene groups on average and having at least one fatty acid ester group.
  • compound Y is selected from PEG-6 Caprylic/capric glycerides, PEG-7 Caprylic/capric glycerides, PEG-7 Glyceryl cocoate.
  • nonionic compound Y can be a “glycerolated compound” which refers to any molecule comprising in its chemical structure a glycerol group or a chain comprising glycerol units -(O-CH2-CHOH-CH2)m, where m is 1 or greater.
  • the glycerolated compound is a polyglycerolated compound meaning that m is 2 or greater.
  • PG is used as an abbreviation of polyglycerol or polyglyceryl.
  • Glycerolated alkyl ethers such as glyceryl lauryl ether
  • Polyglycerolated alkyl ether nonionic surfactants in particular chosen from polygly ceryl-2 oleyl ether and polyglyceryl-4 oleyl ether,
  • Glycerol or poly glycerol esters of fatty acids which are optionally polyhydroxylated, in particular chosen from polyglycerol-2 oleate, polyglyceryl-4 caprate, polygly ceryl-6 caprylate, polyglyceryl-3 dicitrate/stearate, polyglyceryl-10 dioleate, poly glyceryl- 10 laurate, glyceryl stearate citrate.
  • Such a glycerolated Nonionic Compound Y may also optionally be polyoxyalkenate.
  • glycerolated compounds that are also polyoxyalkenated include Polyoxyethylenated alkylglycendes, in particular chosen from PEG-6 Capryhc/Capnc Glycendes, PEG-60 Almond Glycerides, PEG-10 Olive Glycerides and PEG-45 Palm Kernel Glycerides; PEG-7 Caprylic/capric triglycerides, and PEG-7 Glyceryl cocoate.
  • the compound(s) Y will be chosen from fatty acid esters of polyglycerol, in particular polyglyceryl-2 oleate, polyglyceryl-4 caprate, polyglyceryl-6 caprate, polyglyceryl-10 dioleate; and mixtures thereof
  • the glycerolated compounds Y are chosen from those having a single carbon chain or, if having multiple carbon chains, then the multiple carbon chains are unsaturated.
  • the compound(s) Y according to the invention is preferably present in a content equal or greater than 0.5% by weight. According to a particular embodiment, the compound(s) Y according to the invention is preferably present in a concentration by weight from about 0.5%, 0.75% 1%, 1.5% or 2% to about 2.5%, 4%, 5%, 10%, 15%, 20% or 30% - all percentages by weight relative to the total weight of the composition containing it (them). [00117] According to certain embodiments, the compound Y has a hydrophile-lipophile balance (HLB) greater than 7.
  • HLB hydrophile-lipophile balance
  • the mole ratio of the reactive hydroxyl groups (OH) of the polyphenol(s) X to the hy droxyl groups of the compound(s) Y that are reactive with those of the polyphenol(s) X preferably ranges from 1/3 to 20 (20/1), preferably from 1/2 to 15 (15/1), and preferably from 3/4 to 4 (4/1).
  • the at least one polyphenol X comprising at least two different phenol groups and the at least one nonionic compound Y are present in the composition in a X:Y weight ratio from about 1 : 10 to about 10: 1, such as from about 1 :5 to about 5: 1, such as from about 1 : 3 to about 3: 1, such as from about 1 : 1 to about 3:1.
  • compositions comprising water and at least one C2-C5 monoalcohol are provided.
  • Suitable C2-C5 monoalcohols include ethanol, propanol, butanol, pentanol, isopropanol, isobutanol and isopentanol.
  • the at least one monoalcohol is selected from one or more C2-C4 monoalcohols. Ethanol is particularly preferred.
  • the concentration of C2-C5 monoalcohols in the composition ranges from about 5%, 15%, 25%, 35% or 40% to about 40%, 45% 50% or 55%.
  • the at least one C2-C5 monoalcohol is present in a concentration by weight that is effective to inhibit formation of a precipitate of compound X and compound Y in the composition prior to application.
  • the C2-C5 monoalcohol(s) in the solvent system, is/are present in a weight ratio of (C2-C5 monoalcohol) to (C2-C5 monoalcohol plus water) of at least about 0.3 such as ranging from about 0.3, 0.35, 0.40, 0.45, 0.50, 0.55, 0.60, 0.65, 0.70 or 0.75 to about 0.70, 0.75, 0.80, 0.95, or 0.90.
  • the C2-C5 monoalcohol(s) is/are present in the solvent system in a weight ratio of (C2-C5 monoalcohol) to (C2-C5 monoalcohol plus water) from about 0.70 to about 0.90.
  • the remainder of the solvent system is water (i.e., the solvent system is substantially free or free of solvents other than water and C2-C5 monoalcohol.
  • the concentration by weight of water in the composition ranges from about 10% to about 40%, 50% or 60%.
  • the water in the solvent system, is present in in a weight ratio of water to (C2-C5 monoalcohol plus water) from about 0.10, 0.20, or 0.30 to about 0.30, 0.40, 0.50, 0.60 or 0.70.
  • the various ingredients are present such that: the at least one C2-C5 monoalcohol (e.g., ethanol) is present in a concentration by weight in the composition from about 5% to about 55%, the water is present in a concentration by weight in the composition from 10% to about 40%, compound X and compound Y are each independently present in a concentration by weight from about 0.5% to about 25%, and the at least one C2-C5 monoalcohol is present in a concentration such that a weight ratio of (C2-C5 monoalcohol) to (C2- C5 monoalcohol plus water) is present in a weight ratio of at least about 0.3, such as at least about 0.4, such as at least about 0.5, such as at least about 0.6, such as at least about 0.7.
  • the at least one C2-C5 monoalcohol e.g., ethanol
  • the water is present in a concentration by weight in the composition from 10% to about 40%
  • compound X and compound Y are each independently present in a concentration by weight from about 0.5% to
  • the solvent component of these embodiments consists essentially of, or consists of, water and C2-C5 monoalcohols.
  • the solvent component of the composition is “free of,” “devoid of’ or “substantially free of’ solvents other than water and C2-C5 monoalcohols.
  • the composition is an emulsion
  • such compositions comprise water, and such compositions optionally may further comprise at least one C2-C5 monoalcohol.
  • Suitable C2-C5 monoalcohols in emulsions include ethanol, propanol, butanol, pentanol, isopropanol, isobutanol and isopentanol.
  • the at least one monoalcohol is selected from one or more C2-C4 monoalcohols. Ethanol is particularly preferred.
  • the concentration of C2-C5 monoalcohols, if present, is desirable to limit the concentration of C2-C5 monoalcohols, if present, to less than about 50%, such as less than about 40% by weight in the composition.
  • the concentration of C2-C5 monoalcohols in the composition ranges from about 0%, 2%, 5%, or 10% to about 10%, 20% 40% .or 50%.
  • solvent system is substantially free or free of solvents other than water and C2-C5 monoalcohol (if present).
  • the concentration by weight of water in the composition ranges from about 10%, 20%, 30% to about 40%, 50%, or 60%.
  • composition is such that: the compound Y has an HLB less than six, the water is present in a concentration by weight in the composition from 5% to about 70%, compound X and compound Y are each independently present in a concentration by weight from about 0.5% to about 25%, and the emulsion meets one or more of the following properties: has a shear modulus, G’ at 0. 1% strain of at least about 150 Pa or has a yield stress of at least 7 Pa.
  • shear modulus, G’ at 0. 1 % strain, and yield stress are measured using methods described in this specification, below.
  • the solvent component of the compositions of the present invention consists essentially of, or consists of, water and C2-C5 monoalcohols.
  • the solvent component of the composition is “free of,” “devoid of’ or “substantially free of’ solvents other than water and C2-C5 monoalcohols.
  • compositions optionally further comprising at least one coloring agent are provided.
  • the at least one coloring agent is preferably chosen from pigments, dyes, such as liposoluble dyes, nacreous pigments, and pearling agents.
  • the composition includes at least one pigment.
  • liposoluble dyes which may be used according to the present invention include Sudan Red, DC Red 17, DC Green 6, B-carotene, soybean oil, Sudan Brown, DC Yellow 11, DC Violet 2, DC Orange 5, annatto, and quinoline yellow.
  • the liposoluble dyes when present, generally have a concentration ranging up to 20% by weight of the total weight of the composition, such as from 0.0001% to 6%, including all ranges and subranges therebetween.
  • the pigments which may be used according to the present invention, may be chosen from white, colored, inorganic, organic, polymeric, nonpolymenc, coated and uncoated pigments.
  • Representative examples of mineral pigments include titanium dioxide, optionally surface-treated, zirconium oxide, zinc oxide, cerium oxide, iron oxides, chromium oxides, manganese violet, ultramarine blue, chromium hydrate, and ferric blue.
  • Representative examples of organic pigments include carbon black, pigments of D & C type, and lakes based on cochineal carmine, barium, strontium, calcium, and aluminum.
  • Nacreous pigments such as mica coated with titanium or with bismuth oxychloride, colored nacreous pigments such as titanium mica with iron oxides, titanium mica with ferric blue or chromium oxide, titanium mica with an organic pigment chosen from those mentioned above, and nacreous pigments based on bismuth oxy chloride may also be used.
  • the pigments may be present in a coloring-effective amount.
  • coloring-effective amount it is meant that the pigments may be present in an amount sufficient to provide visual color, such as when the compositions are applied to the face and observed under standard lighting conditions (e.g., ASTM D1729-2016) on Fitzpatrick skin phototype III.
  • the pigments may be present in the composition in a concentration ranging up to 30% by weight of the total weight of the composition, such as from 2.5% to 20%, and further such as from 5% to 15%, including all ranges and subranges therebetween.
  • compositions of the present invention are free, substantially free, or devoid of coloring agents as defined above.
  • compositions optionally further comprising at least one gelling agent are provided.
  • Suitable gelling agents include amphiphilic polymers.
  • the amphiphilic polymers may compnse at least one ethylemcally unsaturated monomer containing a sulphonic group, in freeform or partially or totally neutralized form.
  • the amphiphilic polymers may comprise at least one hydrophobic portion.
  • the hydrophobic portion present in these polymers preferably contains from 6 to 50 carbon atoms, preferably from 6 to 22 carbon atoms, preferably from 6 to 18 carbon atoms and preferably from 12 to 18 carbon atoms, including all ranges and subranges therebetween.
  • the amphiphilic polymers may have a molar mass ranging from 50,000 g/mole to 10,000,000 g/mole, preferably from 80,000 g/mole to 8,000,000 g/mole, and preferably from 100,000 g/mole to 7,000,000 g/mole.
  • the amphiphilic polymers may be based on at least one ethylenically unsaturated hydrophilic monomer A and on at least one hydrophobic monomer B.
  • the monomer A comprises a strong acid function, in particular a sulphonic acid or phosphonic acid function.
  • the hydrophobic monomer B comprises at least one hydrophobic radical, chosen from: saturated or unsaturated C6-C18 linear alkyl radicals (for example, n-hexyl, n-octyl, n-decyl, n-hexadecyl, n- dodecyl or oleyl); branched alkyl radicals (for example, isostearic) or cyclic alkyl radicals (for example, cyclododecane or adamantane); C6-C18 fluoro or alkylfluoro radicals (for example, the group of formula — (CH2)2 — (CF2)9 — CF3); a cholesteryl radical or radicals derived from cholesterol (for example, cholesteryl hexanoate); aromatic polycyclic groups, for instance naphthalene or pyrene; and silicone or alkylsilicone or alkylfluorosilicone radicals.
  • the amphiphilic polymers may be crosslinked.
  • the crosslinking agents may be chosen from, for example, the polyolefinically unsaturated compounds commonly used for crosslinking polymers obtained by free-radical polymerization.
  • the crosslinking agent is chosen from methylenebisacrylamide, allyl methacrylate or trimethylolpropane triacrylate (TMPTA).
  • TMPTA trimethylolpropane triacrylate
  • the degree of crosslinking preferably ranges from 0.01 mol % to 10 mol %, and preferably from 0.2 mol % to 2 mol %, relative to the polymer, including all ranges and subranges therebetween.
  • amphiphilic polymers may be homopolymers or copolymers.
  • the amphiphilic polymers can be partially or totally neutralized with a mineral base (for example, sodium hydroxide, potassium hydroxide or aqueous ammonia) or an organic base such as monoethanolamine, diethanolamine, triethanolamine, aminomethylpropanediol, N- methylglucamine, or basic amino acids, for instance arginine and ly sine, and mixtures thereof.
  • a mineral base for example, sodium hydroxide, potassium hydroxide or aqueous ammonia
  • organic base such as monoethanolamine, diethanolamine, triethanolamine, aminomethylpropanediol, N- methylglucamine, or basic amino acids, for instance arginine and ly sine, and mixtures thereof.
  • the amphiphilic polymers may be water-soluble or water-dispersible homopolymers such as, for example, optionally cross-linked polymers of sodium 2-acrylamido-2-methylpropane sulfonate acid such as that used in the commercial product SIMULGEL 800 (CTFA name: Sodium Polyacryloyldimethyl Taurate), cross-linked polymers of ammonium 2-acrylamido-2- methyl propane sulfonate acid (INCI name: AMMONIUM
  • amphiphilic polymers may be chosen from crosslinked or non- crosslinked amphiphilic polymers of 2acrylamido-2-methylpropanesulphonic (AMPS) acid and of at least one ethylenically unsaturated monomer comprising at least one hydrophobic portion containing from 6 to 30 carbon atoms, preferably from 6 to 22 carbon atoms, preferably from 6 to 18 carbon atoms and preferably from 12 to 18 carbon atoms, including all ranges and subranges therebetween.
  • AMPS 2acrylamido-2-methylpropanesulphonic
  • amphiphilic polymers include, but are not limited to, hydrophobically-modified sulfonic acid copolymers such as Ammonium Acryloyldimethyltaurate/VP Copolymer (Aristoflex AVC from Clariant), Ammonium Acryloyldimethyltaurate/Beheneth-25 Methacrylate Crosspolymer (Aristoflex HMB from Clariant) (crosslinked ethoxylated AMPS/behenyl methacrylate), Ammonium Acryloyldimethyltaurate/Steareth-25 Methacrylate Crosspolymer (Aristoflex HMS) (ethoxylated copolymer of AMPS/stearyl methacrylate crosslinked with trimethylol triacrylate), Aristoflex SNC (crosslinked ethoxylated AMPS/C16-C18), Aristoflex LNC (noncrosslinked AMPS/C12-C14), and mixtures thereof.
  • the gelling agent is an acrylic acid polymer, such as a high molecular weight homo or copolymer of acrylic acid that may be crosslinked with a poly alkenyl poly ether- e.g., a “carbomer.”
  • the gelling agent(s) is/are present in the compositions of the present invention in amounts ranging from about 0.05 to about 5% by weight, preferably from 0.1 to 2.5% by weight, preferably from 0.3 to 2% and preferably from 0.5 to 1% by weight, all weights based on the weight of the composition as a whole, including all ranges and subranges therebetween such as, for example, 0.1 to 1.5%, 0.25 to 1.25%, 0.4 to 0.75%, etc.
  • compositions of the present invention may optionally further comprise at least one oil.
  • Oil means any non-aqueous medium which is liquid at ambient temperature (25 °C) and atmospheric pressure (760 mm Hg). Suitable oils can be volatile or non-volatile.
  • Suitable oils include volatile silicone oils.
  • volatile silicone oils include linear or cyclic silicone oils having a viscosity at room temperature less than or equal to 6cSt 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, dodecamethylcyclohexasiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane and their mixtures.
  • volatile oils which may be used include KF 96A of 6 cSt viscosity, a commercial product from Shin Etsu having a flash point of 94°C.
  • the volatile silicone oils Preferably, have a flash point of at least 40°C.
  • Suitable oils include 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 Ci6 alkanes such as C8 to Ci6 isoalkanes (also known as isoparaffins), isododecane, isodecane, and for example, the oils sold under the trade names of Tsopar or Permethyl.
  • the volatile non-silicone oils have a flash point of at least 40°C.
  • Suitable oils include synthetic oils or esters of formula R5COOR6 in which Rs represents a linear or branched higher fatty acid residue containing from 1 to 40 carbon atoms, including from 7 to 19 carbon atoms, and R6 represents a branched hydrocarbon-based chain containing from 1 to 40 carbon atoms, including from 3 to 20 carbon atoms, with Re + R7 ⁇ 10, such as, for example, Purcellin oil (cetostearyl octanoate), isononyl isononanoate, C12 to C15 alkyl benzoate, isopropyl myristate, 2-ethylhexyl palmitate, and octanoates, decanoates or ricinoleates of alcohols or of polyalcohols; hydroxylated esters, for instance isostearyl lactate or diisostearyl malate; pentaerythritol esters; and synthetic ethers containing from 10 to 40 carbon atoms.
  • the oil(s) is/are present in the compositions of the present invention in an amount ranging from about 0.1% to about 20% by weight, more preferably from about 0.4% to about 15% by weight, and preferably from about 0.5% to about 10% by weight, based on the total weight of the composition, including all ranges and subranges within these ranges.
  • compositions of the present invention are substantially free of, devoid of, or free of oils.
  • the composition may be an emulsion.
  • the emulsion has external fatty phase and as such may be a water-in-oil (or water-in silicone) emulsion.
  • the fatty phase generally includes one or more oils, waxes, silicones, and/or other water-insoluble ingredients.
  • composition of the invention can also comprise any additive usually used in the field under consideration.
  • additional film forming agents such as poly(12-hydroxy stearic acid), sunscreens, preserving agents, fragrances, fillers, neutralizing agents, cosmetic and dermatological active agents, moisturizers, silicone elastomers, chelating agents and mixtures thereof can be added.
  • compositions of the invention include at least one rheology modifier and/or at least one filler.
  • Rheology modifiers include ingredients whose function is to modify rheological properties. Such ingredients include natural gums, natural or synthetic polymers, clays, and the like.
  • Fillers include ingredients whose function is create bulk, slip or texture and may secondarily modify rheology as well.
  • ingredients include, for example, boron nitride, starch powders, talc, mica, rice powders, silicas, and the like.
  • Additional fdm-forming agents include for example silicones such as silicone resins, urethanes, or any of various hydrocarbon film forming polymers such as those including acrylic functionality (ethylenic unsaturation), polyester functionality, vinyl functionality, and the like.
  • Humectants as one skilled in the art will recognize include for example, poly hydric alcohols, such as glycerin and various glycol such as butylene glycol, hexylene glycol, hydroxy ethyl urea and the like.
  • 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 eyelashes of human beings.
  • methods of caring for, and/or making up, and/or care for keratinous material by applying compositions of the present invention to the keratinous material in an amount sufficient to care for, and/or to make up, and/or to prime for caring for and/or making up the keratinous material are provided.
  • “making up” the keratin material includes applying at least one coloring agent to the keratin material (in either the composition itself or in a color coat compostion applied over the composition) in an amount sufficient to provide color to the keratin material.
  • the compositions of the present invention are applied topically to the desired keratinous material in an amount sufficient to care for, and/or to make up, and/or to prime for caring for and/or making 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, a color coat composition or a topcoat applied over the composition).
  • the composition is allowed to dry for about 1 minute or less, more preferably for about 45 seconds or less.
  • the compositions may be used in particular, as a makeup foundation or for other facial makeup (for example, exclusive of the eye area and/or lip area) such as blush, concealer, highlighter, bronzer and the like.
  • Example IA Sample Formulations With Polyoxyethylenated Nonionic Compound Y and Ethanol Tolerance Testing
  • Sample formulations were prepared by first making a stock solution of eight grams ethanol, 1 gram of water, 1 gram of tannic acid, and 1 gram of a polyoxyethylenated nonionic compound Y. Water was sequentially added to the stock solution in order to achieve a monoalcohol/total solvent ratio (in this case, %monoalcohol/ (%monoalcohol + %water) that was 0 8. The appearance of turbidity or precipitation was noted. Additional water was then added to achieve an alcohol/total solvent ratio was 0.75. The appearance of turbidity or precipitation was again noted. This was continued to ratios of 0.70 and then additionally in increments of 0.05 until 0.30 was reached. Results were recorded as “clear,” (C) or showing turbidity or a precipitate (X).
  • Example IB Sample Formulations With Polyoxyethylenated Nonionic Compound Y and Wear Testing
  • Sample formulations were prepared by combining and mixing the ingredients below to form various test compositions, each identical except for the polyoxyethylenated nonionic compound Y.
  • Water resistance testing was performed by applying 20 microliters of sample formulation on a dry forearm, followed by spreading the sample evenly with finger over a 3 cm by 3cm square area. Samples were dried (typically 45 minutes) at ambient conditions, then rubbed with fingers under lukewarm running water. Samples were rubbed down the length of the arm toward the wrist and then backward toward the elbow 10 times (for a total of 20 passes over each sample deposit). Remaining color was compared to the initial color of the deposit, evaluated visually then given a comparative scoring.
  • compositions were prepared and evaluated for ethanol tolerance (clarity/turbidity/precipitate) by first mixing tannic acid (5 wt.%), water (52.25 wt.%), and ethanol (42.75 wt.%) to form a first stock solution of tannic acid: and PEG-6 CCG (5 wt.%) in water (52.25 wt.%), and ethanol (42.75 wt.%) to form a second stock solution of polyoxyethanol compound.
  • the first and second stock solutions were mixed in varying volume ratios (1 :3 to 3: 1) to form five test compositions such that the test compositions had an approximate weight ratio of X: Y as shown in Table 3, below, which also shows test results.
  • a “C” indicates a clear composition and “X” indicates mild turbidity.
  • Table 3 Ethanol Tolerance Testing
  • Example IIA Sample Formulations With Glycerolated Nonionic Compound Y and Ethanol Tolerance Testing
  • Sample fonnulations were prepared by first making a stock solution of eight grams ethanol, 1 gram of water, 1 gram of tannic acid, and 1 gram of a glycerolated nonionic compound Y. Water was sequentially added to the stock solution in order to achieve a monoalcohol/total solvent ratio (in this case, %monoalcohol/ (%monoalcohol + %water) that was 0.8. The appearance of turbidity or precipitation was noted. Additional water was then added to achieve an alcohol/total solvent ratio was 0.75. The appearance of turbidity or precipitation was again noted. This was continued to ratios of 0.70 and then additionally in increments of 0.05 until 0.30 was reached. Results were recorded as “clear,” (C) or showing turbidity or a precipitate (X). The results are shown in Tables 1 and 2 below:
  • Sample formulations were prepared by combining and mixing the ingredients below to form various test compositions, each identical except for the polyoglycerolated nonionic compound Y.
  • Table 3 Water Resistance testing Example IIC - Evaluation of X:Y Ratios (Polyphenol: Glvcerolated Compound) for Ethanol Tolerance.
  • compositions were prepared and evaluated for ethanol tolerance (clarity/turbidity/precipitate) by first mixing tannic acid (5 wt.%), water (52.25 wt.%), and ethanol (42.75 wt.%) to form a first stock solution of tannic acid; and polyglyceryl-6 caprylate (5 wt.%) in water (52.25 wt.%), and ethanol (42.75 wt.%) to form a second stock solution of polyglycerolated compound.
  • the first and second stock solutions were mixed in varying volume ratios (1:3 to 3: 1) to form five test compositions such that the test compositions had an approximate weight ratio of X:Y as shown in Table 3, below, which also shows test results.
  • a “C” indicates that all test compositions were clear composition and showed no discernible turbidity or precipitation.
  • Sample gel formulations were prepared by mixing various ingredients to form an emulsion having an external fatty phase.
  • the samples differed only with respect to type of acid and pH of aqueous phase.
  • the compositions and pHs are shown below in Table 1.
  • Phase A The samples were made by combining the ingredients of Phase A sequentially at 50°C using a Silverson Rotor-Stator homogenizer. Ingredients of Phase Bl B2, and B3 were separately prepared, heated to 50°C, and then combined together to form a combined B phase that was then added to Phase A and emulsified using the homogenizer. Phase C (particulate fillers) was added after reducing temperature to below 45°C. Table 1
  • Ex. 1 is consistent with embodiments of the invention described herein.
  • Comp 1 no acid
  • Comp 2 replaces tannic acid with same mass of citric acid, no pH correction
  • Comp 3 replaces tannic acid with enough citric acid, to approximate the pH of Ex. 1 are comparative.
  • Example IIIB Evaluation of Rheology of Emulsion Compositions.
  • compositions were evaluated for rheological properties: (a) storage modulus (G’ measured at 0.1% strain); (b) yield stress at onset; (c) viscosity at a shear rate of 0.01 s’ 1 ; and (d) viscosity at a shear rate of 93 s’ 1 .
  • Yield stress also called apparent yield stress, is the point at which a material undergoes plastic deformation.
  • a material with a yield stress evaluated with dynamic rheology will ty pically exhibit G’ higher than G” at low oscillatory stress.
  • G’ will be relatively constant with increasing oscillatory stress, until at some stress value G’ values will suddenly decrease.
  • G’ and yield stress were determined as follows: using a Discovery HR-3 Rheometer by TA Instruments, with a 40mm 2° steel cone-and-plate geometry, an oscillation amplitude sweep is performed at 1.0 rad/s from 0.01% strain to 100% strain, with 10 points per decade. Afterward, the G’ (Pa) is plotted on the y-axis and oscillation stress (Pa) on the x-axis, both in log-scale. G’ measured at 0.1% strain is recorded. The analysis software is utilized to perform an onset-point analysis which is the apparent yield stress.
  • Viscosity was determined using a Discovery HR-3 Rheometer by TA Instruments, having 40 mm 2° cone-and-plate stainless steel geometry. A flow Ramp was performed in log-mode from 0.001 (1/s) to 1000 (1/s) shear rate with 10 points per decade over a duration of 600 seconds at a temperature of 25°C.

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Abstract

L'invention concerne des compositions, en particulier des compositions de fondation pour produits cosmétiques, comprenant (1) au moins un polyphénol X comprenant au moins deux groupes phénol différents ; (2) au moins un composé non ionique Y, ainsi que des procédés d'utilisation des compositions.
PCT/US2023/020491 2022-04-28 2023-04-28 Compositions comprenant un polyphénol et un composé non ionique y WO2023212375A1 (fr)

Applications Claiming Priority (12)

Application Number Priority Date Filing Date Title
US17/731,815 2022-04-28
US17/731,815 US20230346653A1 (en) 2022-04-28 2022-04-28 Emulsion compositions comprising a polyphenol and low hlb nonionic compound
US17/731,809 US20230346681A1 (en) 2022-04-28 2022-04-28 Compositions comprising a polyphenol and a glycerolated compound
US17/731,809 2022-04-28
US17/731,802 US20230346658A1 (en) 2022-04-28 2022-04-28 Compositions comprising a polyphenol and a polyoxyalkenated compound
US17/731,802 2022-04-28
FRFR2206832 2022-07-05
FR2206831A FR3137567A1 (fr) 2022-07-05 2022-07-05 Compositions d’émulsion comprenant un polyphénol et un composé non ionique a hlb faible
FRFR2206831 2022-07-05
FR2206835A FR3137568A1 (fr) 2022-07-05 2022-07-05 Compositions comprenant un polyphénol et un composé polyoxyalkyléné
FRFR2206835 2022-07-05
FR2206832A FR3137571A1 (fr) 2022-07-05 2022-07-05 Compositions comprenant un polyphénol et un composé glycérolé

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FR3117357A1 (fr) * 2020-12-15 2022-06-17 L'oreal Procédé de revêtement des matières kératiniques consistant à appliquer un agent de revêtement formé par liaisons hydrogène d’un polyphénol avec un composé apte à réagir avec celui-ci
FR3117350A1 (fr) * 2020-12-15 2022-06-17 L'oreal Procédé de revêtement cosmétique en milieu anhydre avec un produit d’interaction d’un polyphénol avec un composé à liaisons hydrogène
FR3117361A1 (fr) * 2020-12-15 2022-06-17 L'oreal Procédé de maquillage des matières kératiniques appliquant une couche de revêtement formée par interaction d’un polyphénol avec un composé à liaisons hydrogène et une couche de maquillage
FR3117362A1 (fr) * 2020-12-15 2022-06-17 L'oreal Procédé de revêtement des matières kératiniques avec un agent de revêtement formé par liaisons hydrogène d’un polyphénol avec un composé non-ionique polyoxyalkyléné, monoet/ ou polyglycérolé

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FR3117357A1 (fr) * 2020-12-15 2022-06-17 L'oreal Procédé de revêtement des matières kératiniques consistant à appliquer un agent de revêtement formé par liaisons hydrogène d’un polyphénol avec un composé apte à réagir avec celui-ci
FR3117350A1 (fr) * 2020-12-15 2022-06-17 L'oreal Procédé de revêtement cosmétique en milieu anhydre avec un produit d’interaction d’un polyphénol avec un composé à liaisons hydrogène
FR3117361A1 (fr) * 2020-12-15 2022-06-17 L'oreal Procédé de maquillage des matières kératiniques appliquant une couche de revêtement formée par interaction d’un polyphénol avec un composé à liaisons hydrogène et une couche de maquillage
FR3117362A1 (fr) * 2020-12-15 2022-06-17 L'oreal Procédé de revêtement des matières kératiniques avec un agent de revêtement formé par liaisons hydrogène d’un polyphénol avec un composé non-ionique polyoxyalkyléné, monoet/ ou polyglycérolé

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