WO2023212372A1 - Compositions appropriées en tant que fixateurs - Google Patents

Compositions appropriées en tant que fixateurs Download PDF

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Publication number
WO2023212372A1
WO2023212372A1 PCT/US2023/020488 US2023020488W WO2023212372A1 WO 2023212372 A1 WO2023212372 A1 WO 2023212372A1 US 2023020488 W US2023020488 W US 2023020488W WO 2023212372 A1 WO2023212372 A1 WO 2023212372A1
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Prior art keywords
composition
compound
weight
compositions
peg
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PCT/US2023/020488
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English (en)
Inventor
Brady ZARKET
Yixin Yang
Anne-Laure Suzanne BERNARD
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L'oreal
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Priority claimed from US17/731,733 external-priority patent/US20230346672A1/en
Priority claimed from FR2206844A external-priority patent/FR3137569A1/fr
Application filed by L'oreal filed Critical L'oreal
Publication of WO2023212372A1 publication Critical patent/WO2023212372A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/25—Silicon; Compounds thereof
    • 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
    • A61K8/34—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
    • A61K8/39—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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—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
    • 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

Definitions

  • compositions in particular setter compositions for cosmetics, comprising (1) at least one polyphenol X comprising at least two different phenol groups; (2) at least one (poly)glycerolated and/or polyoxyalkylenated nonionic compound Y; (3) a solvent system comprising (i) water in an amount of at least about 10% by weight with respect to the total weight of the composition; and (ii) 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; and (4) at least one non-mineral filler, as well as to methods, kits and sets comprising such compositions in container(s) or in application.
  • compositions comprising a silicone resin as coating 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).
  • a silicone resin as coating agent
  • Long-lasting makeup products for the eyelashes and/or the eyebrows use, for their part, waxes or film-forming polymer particles in aqueous suspension of the latex type (i.e.: styrene/acrylate copolymers).
  • 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 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 colour of the makeup on keratin materials, combined with a good level of comfort in comparison with conventional systems, in particular based on silicone resin.
  • CN108175765 is titled “Acid-sensitive controlled-release antiinflammatory gel as well as preparation method and application thereof,” where the purpose is to design a hyaluronic acid hydrogel structure according to the characteristics of pH drop caused by the accumulation of inflammatory metabolites in the joint cavity, to provide an acid-sensitive controlled-release anti-inflammatory gel which is formed by phenylboronic acid-modified hyaluronic acid and tannic acid under neutral to weakly alkaline conditions.
  • US 8,377,853 (corresponding to CA2649412) is titled “Aqueous gels for well bore strengthening” and discloses in the abstract “A process for treating an earth formation is disclosed, the process may include: injecting a gelling agent into the earthen formation; injecting a crosslinking agent into the earthen formation; and reacting the gelling agent and the crosslinking agent to form a gel.
  • the gelling agent may include at least one of a lignin, a lignosulfonate, a tannin, a tannic acid, a modified lignin, a modified lignosulfonate, a modified tannin, a modified tannic acid, biopolymers, starches, carboxy methyl cellulose, polyacrylates, polyacrylamides, polyamines, polyether amines, poly vinyl amines, polyethylene imines, and combinations thereof.
  • the crosslinking agent may include at least one of ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, butylene glycol diglycidyl ether, sorbitol polyglycidyl ether, trimethylolpropane triglycidyl ether, sorbitol polyglycidyl ether, diglycidyl ether of neopentyl glycol, epoxidized 1,6-hexanediol, aziridine derivatives, epoxy functionalized polyalkalene glycols, an oxidized starch, a polymeric dialdehyde, an aldehyde adduct, a tetra methoxy propane, a hydrolized acetal, and combinations thereof.”
  • compositions such as setter compositions having improved properties with respect to composition ease of 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 polyphenol stability' with respect to hydrolysis, aggregation and/or oxidation which affects composition color stability, composition viscosity and/or composition stability (e.g., phase separation).
  • polyphenols such as tannic acid
  • properties such as improved polyphenol stability' with respect to hydrolysis, aggregation and/or oxidation which affects composition color stability, composition viscosity and/or composition stability (e.g., phase separation).
  • one aspect of the present invention is a composition, in particular a setter composition, which has improved properties with respect to composition ease of 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 polyphenol stability with respect to hydrolysis, aggregation and/or oxidation which affects composition color stability, composition viscosity and/or composition stability (e.g., phase separation).
  • compositions in particular setter compositions for cosmetics, comprising (1) at least one polyphenol X comprising at least two different phenol groups, (2) at least one (poly)glycerolated and/or poly oxy alky lenated nonionic compound Y, (3) a solvent system comprising (i) water in an amount of at least about 10% by weight with respect to the total weight of the composition; and (ii) 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, and (4) at least one non-mineral fdler.
  • the composition further comprises at least one gelling agent.
  • the composition is a gel composition and/or has a pH less than 7.
  • the present invention also relates to methods of 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 the keratinous material.
  • the present invention also relates to methods of setting a cosmetic composition (e.g., color coat composition) and/or priming keratinous material for a cosmetic composition (e.g., color coat composition) by applying compositions of the present invention to the keratinous material (priming) and/or to a cosmetic composition (e.g., color coat composition) previously- applied to keratinous material (setting) in an amount sufficient to prime the keratinous material for the cosmetic composition and/or in an amount sufficient to obtain setting of the previously-applied cosmetic composition to keratinous material.
  • a cosmetic composition e.g., color coat composition
  • priming keratinous material for a cosmetic composition e.g., color coat composition
  • kits comprising, as separate compositions in one or more containers within the kits, (A) a composition, in particular a setter composition for cosmetics, comprising (1) at least one polyphenol X comprising at least two different phenol groups, (2) at least one (poly)glycerolated and/or polyoxyalkylenated nonionic compound Y, (3) a solvent system comprising (i) water in an amount of at least about 10% by weight with respect to the total weight of the composition; and (ii) 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, and (4) at least one non-mineral filler; and (B) at least one color coat composition comprising at least one colorant.
  • the composition further comprises at least one gelling agent.
  • the composition is a gel composition and/or has a pH less than 7.
  • the present invention also relates to sets, as applied onto keratinous material, comprising (A) at least one first layer of at least one color coat composition; and (B) at least one second layer of at least one composition, in particular a setter composition for cosmetics, comprising (1) at least one polyphenol X comprising at least two different phenol groups, (2) at least one (poly)glycerolated and/or polyoxyalkylenated nonionic compound Y, (3) a solvent system comprising (i) water in an amount of at least about 10% by weight with respect to the total weight of the composition; and (ii) 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, and (4) at least one non-mineral filler.
  • a setter composition for cosmetics comprising (1) at least one polyphenol X comprising at least two different phenol groups, (2) at least one (poly)glycerolated and/or polyoxyalkylenated noni
  • the at least one second layer is applied over the at least one first layer (in which case the second layer is a setter layer formed by application of a setter composition to the first layer).
  • the at least one first layer is applied over the at least one second layer
  • the at least one second layer is a primer layer formed by application of a primer composition over keratinous material.
  • the composition further comprises at least one gelling agent.
  • the composition is a gel composition and/or has a pH less than 7.
  • “About” as used herein means within 10% of the indicated number (e.g. “about 10%” means 9% - 11% and “about 2%” means 1.8% - 2.2%).
  • At least one means one or more and thus includes individual components as well as mixtures/combinations.
  • 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.
  • ‘Film former”, “film-forming polymer” or “film-forming agent” as used herein 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.
  • “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.
  • 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, amide groups, halogen containing groups, ester groups, thiol groups, sulphonate groups, thiosulphate groups, siloxane groups, and polysiloxane groups.
  • the substituent(s) may be further substituted.
  • Volatile as used herein, means having a flash point of less than about 100°C.
  • Non-volatile as used herein, means having a flash point of greater than about 100°C.
  • Polymer as used herein means a compound which is made up of at least two monomers.
  • Free or “substantially free” or “devoid of' as it is used herein means that while it is preferred that no amount of the specific component be present in the composition, it is possible to have very small amounts of it in the compositions of the invention provided that these amounts do not materially affect at least one, preferably most, of the advantageous properties of the conditioning compositions of the invention.
  • TEA triethanolamine
  • 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.
  • compositions of the present invention are preferably 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 over short period of time (e.g. less than 10 seconds).
  • G' (storage modulus) is higher than G” (loss modulus) at all range of strains up to 300% strain.
  • G’ (storage modulus) is higher than G” (loss modulus) at low strain, but with G’ decreasing and G” increasing, the a gel has the 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 parallel plate geometry on a stainless steel flat peltier plate. 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 1000.0%. 5 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 plant without having undergone any chemical modification.
  • 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.
  • Precipitate or “precipitation” refers to the result of hydrogen bonding interaction between the polyphenol X and the compound Y in the composition.
  • Aggregate or “aggregation” refers to the result of decomposition of polyphenol X in the composition owing to reactions such as hydrolysis and/or oxidation.
  • compositions and methods of the present invention can comprise, consist of, or consist essentially of the essential elements and limitations of the invention described herein, as well as any additional or optional ingredients, components, or limitations described herein or otherwise useful.
  • the solvent system can “consist essentially of’ water and C2-C5 monoalcohol
  • the surfactant system 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 “polyphenol stability as evidenced by composition viscosity stability and/or composition stability (e.g., phase separation).”
  • 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, acutis simin, tellimagrandins, sanguiin, potentillin, pedunculagin, geraniin, chebulagic acid, repandisinic acid, ascorgeraniin, stachyurin, casuarinin, casuariin, punicacortein, coriariin, cameliatannin, isodeshy drodigalloyl, dehydrodigalloyl, hellinoyl, punicalagin and rh
  • catechin tannins such as gallotannins
  • 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, preferably equal or greater than 0.8% by weight, preferably equal or greater than 1% by weight, preferably equal or greater than 2% by weight relative to the total weight of the composition containing it (them).
  • the polyphenol(s) X according to the invention is preferably present in a content from about 0.5 to about 30% by weight, preferably from about 0.75 to about 25% by weight, preferably from about 1 to about 25% by weight, and preferably from about 2 to about 15% by weight, relative to the total weight of the composition containing it (them), including all ranges and subranges therebetween such as, for example, 3 to 8% by weight, 0.5% to 7.5% by weight, 2 to 5% by weight, etc.
  • compositions comprising at least one (poly)glycerolated and/or polyoxyalkylenated nonionic compound Y are provided.
  • nonionic compound Y has a molar mass greater than 200 g/mol.
  • polyoxyalkylenated compound refers to any molecule comprising in its chemical structure at least chain comprising oxyalkylene units, in particular oxyethylene units - (OCH2CH2)n and/or oxypropylene units - (OCFLCFLCFhjp, where n and p are 2 or greater.
  • polyglycerolated compound 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 2 or greater; “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, where m is 1; and “(poly)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, where m is 1 or greater.
  • the molar mass of the compound Y is greater than 350 g/mol.
  • Glycerolated alkyl ethers such as glyceryl lauryl ether
  • Glycerol or polyglycerol esters of fatty acids which are optionally polyhydroxylated, in particular chosen from polyglyceryl-3 polyricinoleate, polyglyceryl-2 dhsostearate, polyglyceryl-4 dhsostearate, polyglyceryl-4 caprate, polyglyceryl-2 stearate, polyglyceryl-3 dicitrate/stearate, polyglyceryl-10 dioleate, polyglyceryl-3 diisostearate, polyglyceryl-2 triisostearate, polyglyceryl-10 laurate, glycery l stearate citrate and polyglyceryl-2 dipoly hy droxy s tearate,
  • Polyoxyethylenated or (poly)glycerolated waxes notably chosen from polyoxyethylenated ester waxes such as polyoxyethylenated jojoba wax, PEG-8 Beeswax, PEG- 60 Lanolin, PEG-75 Lanolin, PPG-12-PEG-50 Lanolin and Polyglyceryl-3 Beeswax, [0081] (5) Polyethylene glycols of the type H(O-CH2-CH2)n-OH, in particular chosen fromPEG-6, PEG-8, PEG-14M, PEG-20, PEG-45M, PEG-90, PEG-90M, PEG-150, PEG-180 and PEG-220,
  • Alkylpolyethylene glycols of the type CnH2n+i-(0-CH2-CH2)o-OH in particular chosen from Ceteth-2, Ceteth-10, Ceteth-20, Ceteth-25, Isoceteth-20, Laureth-2, Laureth-3, Laureth-4, Laureth-12, Laureth-23, Oleth-2, Oleth-5, Oleth-lO, Oleth-20, Oleth-25, Deceth-3, Deceth-5, Beheneth-10, Steareth-2, Steareth-10, Steareth-20, Steareth-21, Steareth-100, Ceteareth-12, Ceteareth-15, Ceteareth-20, Ceteareth-25, Ceteareth-30, Ceteareth-33, Coceth-7 and Trideceth-12,
  • Polysorbates in particular chosen from Polysorbate-20, Polysorbate-21, Polysorbate-60, Polysorbate-61, Polysorbate-80 and Polysorbate-85,
  • the compound(s) Y according to the invention is preferably present in a content equal or greater than 0.5% by weight, preferably equal or greater than 0.8% by weight, preferably equal or greater than 1% by weight, more particularly equal or greater than 2% by weight relative to the total weight of the composition containing it (them).
  • the compound(s) Y according to the invention is preferably present in a content from about 0.5 to about 30% by weight, preferably from about 0.75 to about 25% by weight, preferably from about 1 to about 25% by weight, and preferably from about 2 to about 15% by weight, relative to the total weight of the composition containing it (them), including all ranges and subranges therebetween such as, for example, 3 to 8% by weight, 0.5% to 7.5% by weight, 2 to 5% by weight, etc.
  • the mole ratio of the reactive hydroxyl groups (OH) of the polyphenol(s) X to the hydroxyl 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).
  • compositions comprising a solvent system comprising (i) water in an amount of at least about 10% by weight with respect to the total weight of the composition; and (ii) 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 are provided.
  • Suitable C2-C5 monoalcohols include ethanol, propanol, butanol, pentanol, isopropanol, isobutanol and isopentanol. Ethanol is particularly preferred.
  • the C2-C5 monoalcohol(s) is/are present in the compositions of the present invention in an amount effective to inhibit formation of a precipitate of compound X and compound Y in the composition prior to application.
  • the C2-C5 monoalcohol(s) is/are present in the compositions of the present invention in amounts ranging from about 5% to about 75%, preferably from about 10% to about 65%, preferably from about 20% to about 55%, and preferably from about 25% to about 50%, by weight, based on the total weight of the composition, including all ranges and subranges in between such as, for example, about 25% to about 65%.
  • the compositions of the present invention further comprise water.
  • the compositions comprise at least about 10% water by weight, preferably in amounts from about 10% to about 75%, preferably from about 15% to about 65%, preferably from about 20% to about 55%, and preferably from about 25% to about 50%, by weight, based on the total weight of the composition, including all ranges and subranges therebetween such as, for example, about 35% to about 55%.
  • 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 of the present invention are devoid of, free of, or substantially free of, oils
  • compositions of the present invention are devoid of, free of, or substantially free of, waxes.
  • compositions further comprising at least one non-mineral filler are provided.
  • “Non-mineral filler” as used herein means filler which does not contain mineral elements, more specifically filler which does not contain more than 1% monovalent or divalent metal compounds.
  • silica containing silicon and oxygen
  • magnesium aluminum silicate and other metal silicates such as lithium magnesium sodium silicate
  • perlite containing significant amounts of aluminum
  • kaolin containing significant amounts of aluminum
  • non-mineral filler(s) have an apparent diameter ranging from 0.01 to 150 pm, preferably from 0.5 to 120 pm, and preferably from 1 to 80 pm.
  • An apparent diameter corresponds to the diameter of the circle into which the elementary particle fits along its shortest dimension (thickness for leaflets).
  • non-mineral filler(s) are lamellar, spherical or oblong.
  • Suitable non-mineral fillers include, but are not limited to, silica, modified and/or unmodified polyamide powders such as Nylon® powder (e.g., nylon 12) and modified polyamide powders such as, for example, modified with a coating or shell (e.g., polyvinylalcohol shell) and/or with an optical brightener attached, poly- -alanine powder, polyethylene powder, acrylic polymer powder and in particular polymethyl methacrylate (PMMA) powder, acrylic acid copolymer powder, polytetrafluoroethylene powders, lauroyllysine, hollow polymer microspheres such as those of poly vinylidene chlbride/acrylonitrile, for instance Expancel® (Nobel Industries), hollow polymer microspheres (Tospearl®from Toshiba, for example), hollow silica microspheres (Silica Beads® from Maprecos), cellulose particles including microcrystalline cellulose particles, and polyester particles.
  • Nylon® powder e.g.,
  • the non-mineral filler(s) may be surface-treated, e.g., to make them lipophilic. However, the non-mineral filler(s) may also be unsurface-treated.
  • suitable surface treatments include, but are not limited to, trimethylsiloxyl groups, which are obtained, for example, by treating fumed silica in the presence of hexamethyldisilazane. Silicas thus treated are known as "silica silylate” according to the CTFA (6th edition, 1995).
  • non-mineral fillers have minimal reaction with polyphenols such that their presence in the invention compositions does not adversely materially affect composition viscosity and/or composition stability (e.g., phase separation), as well as not materially adversely affecting color stability of the compositions.
  • Non-mineral fillers can also provide additional benefits to invention compositions to which they are added, such as, for example, improved optical properties (e g., reflection or glitter), improved texture, and reduced cost of production.
  • the compositions of the invention comprise non-mineral filler(s) in an amount ranging from about 0. 1 to about 10%, preferably from about 0.5 to about 7.5%, preferably from about 0.75 to about 5%, and preferably from about 1 to 3%, by weight, based on the total weight of the composition, including all ranges and subranges therebetween such as, for example, 2 to 5%, 1 to 10%, 0.8 to 5.5%, etc.
  • compositions optionally further comprising at least one gelling agent are provided.
  • suitable gelling agents include any gelling agent capable of providing thickening to a high-alcohol content solvent system such as for example acrylic acid (co)polymers, such as high molecular weight homo- or copolymers comprising acrylic acid, optionally crosslinked with a polyalkenyl polyether, including some polymers identified as “carbomer” as well as amphiphilic polymers.
  • the gelling agent is an amphiphilic polymer.
  • the gelling agents may comprise at least one ethylenically unsaturated monomer, preferably 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 Ce-C is 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); Ce-Cis fluoro or alky I fluoro radicals (for example, the group of formula — (CH2)2 — (CF2)9 — CFs); 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 tnacrylate (TMPTA).
  • TMPTA trimethylolpropane tnacrylate
  • 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
  • POLYACRYLDIMEHYLTAURAM1DE such as the product sold under the tradename HOSTACERIN AMPS@ by Clariant.
  • the amphiphilic polymers may be chosen from crosslinked or noncrosslinked 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(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 Cs to C16 alkanes such as Cs to C16 isoalkanes (also known as isoparaffins), isododecane, isodecane, and for example, the oils sold under the trade names of Isopar 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 RsCOORe 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 Re represents a branched hydrocarbon-based chain containing from 1 to 40 carbon atoms, including from 3 to 20 carbon atoms, with Re + R?
  • 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.
  • compositions of the present invention are substantially free of, devoid of, or free of volatile oils such as, for example, isododecane.
  • compositions of the present invention are substantially free of, devoid of, or free of silicone oils such as, for example, dimethicone.
  • 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.
  • 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 nacreous pigments which may be used according to the present invention may be chosen from white 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 oxychloride.
  • the pigments which may be used according to the present invention, may be chosen from white, colored, inorganic, organic, polymeric, nonpolymeric, 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.
  • the coloring agents may be present in compositions of the present invention in an amount insufficient to provide visual color to the compositions (that is, the color of compositions of the present invention are a result of factor(s) other than the presence of coloring effective amounts of coloring agent, such as for example hydrolysis of polyphenol X which can provide color to the compositions) and/or in an amount insufficient to alter the visual color characteristics of a color cosmetic composition (for example, a makeup composition such as a foundation) when the composition of the present invention is used in conjunction with the color cosmetic composition as a primer or setter composition.
  • a color cosmetic composition for example, a makeup composition such as a foundation
  • compositions of the present invention are free, substantially free, or devoid of coloring agents as defined above.
  • composition of the invention can also comprise any additive usually used in the field under consideration.
  • film forming agents, waxes, dispersants such as poly(12-hydroxystearic acid), sunscreens, preserving agents, fragrances, chelating agents, vitamins, antioxidants, neutralizing agents, cosmetic and dermatological active agents, moisturizers, silicone elastomers, and mixtures thereof can be added.
  • suitable additional components can be found in the other references which have been incorporated by reference in this application. Still further examples of such additional ingredients may be found in the International Cosmetic Ingredient Dictionary and Handbook (9 th ed. 2002).
  • preferred embodiments of the present invention include compositions which are “free,” substantially free” or “devoid” of the ingredients discussed in this paragraph such as film forming agents and waxes.
  • composition of the invention should be cosmetically or dermatologically acceptable, i.e., it should contain anon-toxic physiologically acceptable medium and should be able to be applied to the eyelashes of human beings.
  • compositions of the present invention are provided.
  • preferred embodiments of the present invention include methods of priming keratinous material for a cosmetic composition and/or of setting a cosmetic composition which has been previously applied to keratinous material by applying compositions of the present invention over keratinous material prior to application of a cosmetic composition (priming) and/or by applying compositions of the present invention over a cosmetic composition previously-applied to keratinous material (setting).
  • “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 either over or under the composition as described above) 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.
  • 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.
  • compositions having stable composition viscosity and/or composition stability comprising (1) at least one polyphenol X comprising at least two different phenol groups, (2) at least one (poly)glycerolated and/or polyoxyalkylenated nonionic compound Y, and (3) a solvent system comprising (i) water in an amount of at least about 10% by weight with respect to the total weight of the composition; and (n) 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, wherein the method comprises adding at least one non-mineral filler to the composition during preparation of the composition in an amount sufficient to produce a composition having stable composition viscosity and/or composition stability (e.g., phase separation). The amount of the at least one non-mineral filler added to the composition during preparation
  • kits comprising, as separate compositions in one or more containers within the kits, (A) a composition, in particular a setter composition for cosmetics, comprising (1) at least one polyphenol X comprising at least two different phenol groups, (2) at least one (poly)glycerolated and/or polyoxyalkylenated nonionic compound Y, (3) a solvent system comprising (i) water in an amount of at least about 10% by weight with respect to the total weight of the composition; and (ii) 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, and (4) at least one non-mineral filler; and (B) at least one other composition such as a color coat composition comprising at least one colorant are provided.
  • the composition further comprises at least one gelling agent.
  • the composition is a gel composition and/or has a pH less than 7.
  • compositions (A) and (B) may be contained in different portions or sections of the same container within the kit. However, compositions (A) and (B) may also be in different containers with the kit.
  • sets, as applied onto keratinous material comprising (A) at least one first layer of at least one composition, in particular a setter composition for cosmetics, comprising (1) at least one polyphenol X comprising at least two different phenol groups, (2) at least one (poly)glycerolated and/or polyoxyalkylenated nonionic compound Y, (3) a solvent system comprising (i) water in an amount of at least about 10% by weight with respect to the total weight of the composition; and (ii) at least one C2-C5 monoalcohol in an amount effective to inhibit fonnation of a precipitate of compound X and compound Y in the composition prior to application, and (4) at least one non-mineral filler; and (B) at least one second layer of a color coat composition comprising at least one colorant, where the at least one second layer is applied over (where the composition of the invention is a primer composition) or under (where the composition of the invention is a setter composition)
  • a composition comprising (a) at least one polyphenol X comprising at least two different phenol groups; (b) at least one (poly)glycerolated and/or polyoxyalkylenated nonionic compound Y; (c) a solvent system comprising (i) water in an amount of at least about 10% by weight with respect to the total weight of the composition; and (ii) 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; and (d) at least one non-mineral filler;
  • composition of the preceding embodiment in the form of a gel composition
  • composition of any preceding embodiment wherein the at least one C2-C5 monoalcohol is ethanol;
  • composition of any preceding embodiment, wherein the at least one nonmineral filler is selected from the group consisting of silica, silica silylate, cellulose, and polyamide;
  • composition of any preceding embodiment comprising (a) from about 0.5 to about 15% by weight of at least one polyphenol X comprising at least two different phenol groups; (b) from about 0.5 to about 15% by weight of at least one (poly)glycerolated and/or polyoxyalkylenated nonionic compound Y; (c) from about 25 to about 65% by weight of at least one C2-C5 monoalcohol; (d) from about 1 to about 10% by weight of at least one non-mineral filler; and (e) from about 20 to about 55% by weight of water, all weights being based on the total weight of the composition;
  • a method of making up keratinous material comprising applying a color coat composition to the keratinous material to form an applied composition, and applying the composition of any preceding embodiment over the applied composition;
  • a method of making up keratinous material comprising applying the composition of any preceding embodiment to the keratinous material to form an applied composition, and applying a color coat composition over the applied composition.
  • compositions were prepared by mixing the ingredients shown in Table 2 and Table 3 below.
  • Each prepared composition contained 2% of different types of mineral (comparative) and non-mineral (invention) fillers as identified in Tables 2 and 3. All compositions were placed into 25°C and 45°C ovens for a period of 8 weeks and visually inspected.
  • Invention compositions containing 2% of non-mineral fillers (1) silica silylate, (2) silica, (3) cellulose, (4) microcrystalline cellulose or (5) polyamide did not have much color change after 8 weeks at 45°C and 8 weeks at 25 °C.
  • Comparative compositions containing 2% of mineral fillers (1) zinc oxide, (2) purified natural silicate, (3) synthesis silicate clay, (4) perlite, or (5) kaolin have significant color changes, become dark yellow, brown or black after 8 weeks at 45°C. Further, compositions containing ZnO or perlite change the color even at room temperature over 8 weeks. These results indicate that invention compositions containing non-mineral filler were substantially more color stable than compositions containing mineral filler.

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  • Epidemiology (AREA)
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Abstract

L'invention concerne des compositions, en particulier des compositions de fixation pour produits cosmétiques, comprenant (1) au moins un polyphénol X comprenant au moins deux groupes phénol différents ; (2) au moins un composé non ionique (poly)glycérolé et/ou polyoxyalkyléné Y ; (3) un système de solvant comprenant (i) de l'eau en une quantité d'au moins environ 10 % en poids par rapport au poids total de la composition ; et (ii) au moins un monoalcool en C2-C5 en une quantité efficace pour inhiber la formation d'un précipité du composé X et du composé Y dans la composition avant l'application ; et (4) au moins une charge non minérale, ainsi que des procédés, des kits et des ensembles comprenant de telles compositions dans le ou les récipients ou dans l'application.
PCT/US2023/020488 2022-04-28 2023-04-28 Compositions appropriées en tant que fixateurs WO2023212372A1 (fr)

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US17/731,733 2022-04-28
US17/731,733 US20230346672A1 (en) 2022-04-28 2022-04-28 Compositions suitable as setters
FRFR2206844 2022-07-05
FR2206844A FR3137569A1 (fr) 2022-07-05 2022-07-05 Compositions appropriées comme fixateurs

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CA2649412A1 (fr) 2006-04-20 2007-11-01 M-I Llc Gels aqueux pour le renforcement de forages de puits
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WO2022128543A1 (fr) * 2020-12-15 2022-06-23 L'oreal Procédé de revêtement de matières kératiniques consistant à appliquer auxdites matières un agent de revêtement formé par interaction du type liaison hydrogène d'un polyphénol avec au moins un composé non ionique polyoxyalkyléné polyglycérolé et/ou monoglycérolé

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CA2649412A1 (fr) 2006-04-20 2007-11-01 M-I Llc Gels aqueux pour le renforcement de forages de puits
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WO2022128543A1 (fr) * 2020-12-15 2022-06-23 L'oreal Procédé de revêtement de matières kératiniques consistant à appliquer auxdites matières un agent de revêtement formé par interaction du type liaison hydrogène d'un polyphénol avec au moins un composé non ionique polyoxyalkyléné polyglycérolé et/ou monoglycérolé

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BEATA KACZMAREK ET AL: "Development of tannic acid-enriched materials modified by poly(ethylene glycol) for potential applications as wound dressing", PROGRESS IN BIOMATERIALS, BIOMED CENTRAL LTD, LONDON, UK, vol. 9, no. 3, 20 September 2020 (2020-09-20), pages 115 - 123, XP021282681, ISSN: 2194-0509, DOI: 10.1007/S40204-020-00136-1 *
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