WO2023212368A1 - Compositions de fixation - Google Patents

Compositions de fixation Download PDF

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Publication number
WO2023212368A1
WO2023212368A1 PCT/US2023/020481 US2023020481W WO2023212368A1 WO 2023212368 A1 WO2023212368 A1 WO 2023212368A1 US 2023020481 W US2023020481 W US 2023020481W WO 2023212368 A1 WO2023212368 A1 WO 2023212368A1
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WO
WIPO (PCT)
Prior art keywords
composition
compound
compositions
glycerolated
poly
Prior art date
Application number
PCT/US2023/020481
Other languages
English (en)
Inventor
Brady ZARKET
Yixin Yang
Anne-Laure Suzanne BERNARD
Treasure BELLAMY
Original Assignee
L'oreal
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US17/731,712 external-priority patent/US20230346657A1/en
Priority claimed from US17/731,759 external-priority patent/US20230346662A1/en
Priority claimed from US17/731,816 external-priority patent/US20230346664A1/en
Priority claimed from FR2206834A external-priority patent/FR3137565A1/fr
Priority claimed from FR2206833A external-priority patent/FR3137572A1/fr
Application filed by L'oreal filed Critical L'oreal
Publication of WO2023212368A1 publication Critical patent/WO2023212368A1/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
    • A61K8/30—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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4993—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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/676—Ascorbic acid, i.e. vitamin C
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—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
    • 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; (4) optionally at least one chelating agent; and (5) optionally at least one antioxidant selected from the group consisting of at least one ascorbic acid compound, at least one sulfur-containing antioxidant, and mixtures thereof, 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 against oxidation and/or hydrolysis leading to aggregation of byproducts.
  • 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 can affect composition color stability.
  • 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; (4) optionally at least one chelating agent; and (5) optionally at least one antioxidant selected from the group consisting of at least one ascorbic acid compound, at least one sulfur-containing antioxidant, and mixtures thereof.
  • the composition further comprises at least one gelling agent.
  • the composition is a gel composition and/or has a pH less than 7.
  • 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 sulfur-containing antioxidant.
  • the composition further comprises at least one gelling agent and/or at least one chelating agent.
  • the composition is a gel composition and/or has a pH less than 7.
  • 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 nonionic compound Y which is a surfactant having a hydrophilic-lipophilic balance (HLB) greater than or equal to 7, has at least one carbon chain having at least 8 carbon atoms, and has at least one (poly)glycerolated chain and/or polyoxyalkylenated chain; 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 (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.
  • the composition further comprises at least one gelling agent.
  • the composition is a gel composition and/or has a pH less than 7.
  • 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, (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, (4) at least one chelating agent, and (5) at least one ascorbic acid compound.
  • the composition further comprises at least one gelling agent.
  • the composition is a gel composition and/or has a pH less than 7.
  • 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 sulfur-containing antioxidant, as well as to methods, kits and sets comprising such compositions in container(s) or in application.
  • 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 nonionic compound Y which is a surfactant having a hydrophilic-lipophilic balance (HLB) greater than or equal to 7, has at least one carbon chain having at least 8 carbon atoms, and has at least one (poly)glycerolated chain and/or polyoxyalkylenated chain; 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 (h) 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, as well as to methods, kits and sets comprising such compositions in container(s) or in application.
  • HLB hydrophilic-lipophilic balance
  • 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; (4) optionally at least one chelating agent; and (5) optionally at least one antioxidant selected from the group consisting of at least one ascorbic acid compound, at least one sulfur-containing antioxidant, and mixtures thereof; and (B) at least one color coat composition comprising at least one colorant.
  • the composition (A) further comprises at least one gelling agent
  • 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; (4) optionally at least one chelating agent; and (5) optionally at least one antioxidant selected from the group consisting of at least one ascorbic acid compound, at least one sulfur- containing antioxidant, and mixtures thereof.
  • 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 in layer (B) further comprises at least one gelling agent.
  • the composition in layer (B) is a gel composition and/or has a pH less than 7.
  • 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 earned 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.
  • Room temperature means 25°C.
  • “Atmospheric pressure” means 760 mmHg, i.e. 10 5 pascals.
  • C oating 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 reduced amount of color darkening or aggregation as defined above.”
  • 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 thearubrms); 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, 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, preferably greater than 250 g/mol, preferably greater than 300 g/mol, preferably greater than 350 g/mol, and preferably less than 5,000 g/mol, preferably less than 3,500 g/mol, preferably less than 2,500 g/mol, including all ranges and subranges therebetween including ranges including the identified weights above such as, for example, 250-1,500 g/mol, 350-3,500 g/mol, etc.
  • 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 - (OCH 2 CH 2 CH2) P , 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.
  • 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 diisostearate, polyglyceryl-4 diisostearate, polyglyceryl-4 caprate, polyglyceryl-2 stearate, polyglyceryl-3 dicitrate/stearate, polyglyceryl-10 dioleate, polyglyceryl-3 dhsostearate, polyglyceryl-2 triisostearate, polyglyceryl-10 laurate, glyceryl stearate citrate and polyglyceryl-2 dipolyhydroxystearate,
  • Polyoxyethylenated or (poly)glycerolated waxes notably chosen from poly oxy ethylenated 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,
  • Polyethylene glycols of the type HtG-CFL-CFLjn-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 CnH 2n +i-(0-CH 2 -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,
  • Poly oxyethylenated alkylglycerides in particular chosen from PEG-6 Caprylic/Capric Glycerides, PEG-60 Almond Glycerides, PEG- 10 Olive Glycerides and PEG-45 Palm Kernel Glycerides,
  • nonionic compound Y is preferably a surfactant having a hydrophilic-lipophilic balance (HLB) of greater than or equal to 7, having at least one carbon chain having at least 8 carbon atoms, and having at least one (poly)glycerolated chain and/or poly oxy alkylenated chain.
  • HLB hydrophilic-lipophilic balance
  • nonionic compound Y has at least one carbon chain having from about 8 to about 50 carbon atoms, preferably from about 8 to about 30 carbon atoms, preferably from about 8 to about 26 carbon atoms, preferably from about 8 to about 22 carbon atoms, preferably from about 8 to about 18 carbon atoms, and preferably from about 8 to about 16 carbon atoms, including all ranges and subranges therebetween such as 10 to 28 carbon atoms, 10 to 20 carbon atoms, 12 to 22 carbon atoms, 16 to 30 carbon atoms, etc.
  • the at least one carbon chain may be unsaturated (for example, oleate) or saturated (for example, caprylate), and/or straight (for example, laurate) or branched (for example, isostearate).
  • nonionic compound Y has only a single carbon chain (for example, an ester such as a caprate), although it is possible that nonionic compound Y has two or more carbon chains (for example, a diester). If two or more carbon chains are present, the chains may be identical (for example, a diester such as a dicaprylate or a triester such as a tri caprate, etc.) or different (for example, a mixture of esters such as those found in natural sources such as rapeseed oil (for example, PEG-4 rapeseedamide) or coconut oil (for example, PEG-7 glyceryl cocoate), or a mixture of esters such as caprate and caprylate).
  • rapeseed oil for example, PEG-4 rapeseedamide
  • coconut oil for example, PEG-7 glyceryl cocoate
  • nonionic compound Y has at least one (poly)glycerolated and/or poly oxy alk lenated chain.
  • Each chain present may respectively contain (poly)glycerolated unit(s) (that is, one or more such units — for example, 2 such units in poly gly eery 1-2 oleate) and/or multiple oxy alkylenated units (that is, two or more such units) (for example, four such units in a polyethyleneglycol-4 (PEG-4) modified compound like PEG-4 caprylate/caprate).
  • PEG-4 polyethyleneglycol-4
  • nonionic compound Y may contain both (poly)glycerolated (for example, a single glyceryl) and poly oxyalkylenated chains, such as in the compound PEG-7 glyceryl cocoate.
  • nonionic compound Y has at least one (poly)glycerolated chain containing one or more glycerolated unit(s) such as, for example, 1 to 100 glycerolated unit(s), preferably 1 to 75 glycerolated unit(s), preferably 1 to 50 glycerolated unit(s), preferably 1 to 25 glycerolated unit(s), preferably 1 to 15 glycerolated unit(s), preferably 1 to 10 glycerolated unit(s), including all ranges and subranges therebetween such as 1 to 8 glycerolated unit(s), 2 to 20 glycerolated units, 3 to 30 glycerolated units, 2 to 9 glycerolated units, and 5 to 25 glycerolated units, etc.
  • glycerolated unit(s) such as, for example, 1 to 100 glycerolated unit(s), preferably 1 to 75 glycerolated unit(s), preferably 1 to 50 g
  • nonionic compound Y has at least one polyoxyalkylenated chain containing two or more oxyalkylenated units such as, for example, 2 to 100 oxyalkylenated units, preferably 2 to 75 oxyalkylenated units, preferably 2 to 50 oxyalkylenated units, preferably 2 to 25 oxyalkylenated units, preferably 2 to 15 oxyalkylenated units, preferably 2 to 10 oxyalkylenated units, including all ranges and subranges therebetween such as 2 to 9 oxyalkylenated units, 3 to 20 oxyalkylenated units, 5 to 30 oxyalkylenated units, 10 to 50 oxyalkylenated units, and 7 to 25 oxyalkylenated units, etc.
  • oxyalkylenated units such as, for example, 2 to 100 oxyalkylenated units, preferably 2 to 75 oxyalkylenated units, preferably 2 to 50 oxyalkylenated units, preferably 2 to
  • nonionic comopund Y has an HLB value of 7 or greater, preferably an HLB value of 8 or greater, preferably an HLB value of 9 or greater, and preferably an HLB value of 10 or greater,
  • nonionic compound Y is selected from the group consisting of surfactants having an HLB value of 7, which have (1) one or more carbon chains having 8 to 30 carbon atoms and one chain having 2 to 9 poly oxyalkylene units, (2) two or more carbon chains having 8 to 30 carbon atoms and one chain having 10 or more poly glycerolated units, (3) a single carbon chain having 8 to 30 carbon atoms and one chain having 2 to 9 polyglycerolated units, or (4) mixtures thereof.
  • 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 chelating agent are provided.
  • chelating agents are known in the art and described, for example, in “Chelating agents” Kirk Othmer Encyclopedia of Chemical Technology, Vol. 5 pp. 708-739, published in 2003 and subsequent editions.
  • Suitable chelating agents include, but are not limited to, polyphosphates, aminocarboxylic acids, 1,3-diketones, hydroxy carboxylic acids, polyamines, amino alcohols, heterocyclic aromatic bases, aminophenols, Schiffs bases, tetrapyrroles, sulfur compounds, synthetic macrocyclic compounds, polymers and phosphonic acids.
  • chelating agents are selected from aminocarboxylic acids.
  • Suitable chelating agents include, but are not limited to, ethylenediaminetetraacetic acid (EDTA), tetrasodium etidronate, tetrasodium pyrophosphate, pentasodium ethylenediamine tetramethylene phosphonate, sodium staminate, tetrasodium glutamate diacetate, tetraacetic acid, DPTA (1,3-diaminopropanetetraacetic acid), and mixtures thereof.
  • EDTA ethylenediaminetetraacetic acid
  • tetrasodium etidronate tetrasodium pyrophosphate
  • pentasodium ethylenediamine tetramethylene phosphonate pentasodium ethylenediamine tetramethylene phosphonate
  • sodium staminate tetrasodium glutamate diacetate
  • tetraacetic acid DPTA (1,3-d
  • the compositions of the invention comprise chelating agent(s) in an amount ranging from about 0.0001 to about 5%, preferably from about 0.0002 to about 3%, preferably from about 0.002 to about 1%, and preferably from about 0.005 to 1 %, by weight, based on the total weight of the composition, including all ranges and subranges therebetween such as, for example, 0.002 to 0.007%, 0.001 to 4%, 0.00025 to 1.25%, etc.
  • compositions further comprising at least one antioxidant selected from the group consisting of ascorbic acid compounds, sulfur-containing antioxidants, and mixtures thereof, are provided.
  • the antioxidant component of the compositions of the present invention consists essentially of, or consists of, ascorbic acid compounds, sulfur-containing antioxidants, and mixtures thereof.
  • the antioxidant component of the composition is “free of,” “devoid of’ or “substantially free of’ antioxidants other than ascorbic acid compounds, sulfur-containing antioxidants, and mixtures thereof.
  • compositions further comprising at least one ascorbic acid compound are provided.
  • the ascorbic acid compound can be vitamin c (ascorbic acid) or substituted versions of vitamin c.
  • Ascorbic acid compound(s) can function as antioxidants in the invention compositions and, thus, are preferably added in antioxidant effective amounts.
  • Suitable ascorbic acid compounds include esters of ascorbic acid (Vitamin C) which include, but are not limited to, water-soluble or fat-soluble ester(s) of ascorbic acid, such as for example tetrahexyldecyl ascorbate, ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl glucoside, glucosamine ascorbate, ascorbyl acetate, and mixtures thereof.
  • esters of ascorbic acid Vitamin C
  • water-soluble or fat-soluble ester(s) of ascorbic acid such as for example tetrahexyldecyl ascorbate, ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl glucoside, glucosamine ascorbate, ascorbyl acetate, and mixtures thereof.
  • the compositions of the invention comprise ascorbic acid compound(s) in an amount ranging from about 0.01 to about 5%, preferably from about 0.05 to about 3%, preferably from about 0.1 to about 1%, and preferably from about 0.25 to 0.75%, by weight, based on the total weight of the composition, including all ranges and subranges therebetween such as, for example, 0.1 to 3%, 0.2 to 1%, 0.075 to 0.75%, etc.
  • the antioxidant component of the compositions of the present invention consists essentially of, or consists of, ascorbic acid compound(s).
  • the antioxidant component of the composition is “free of,” “devoid of’ or “substantially free of’ antioxidants other than ascorbic acid compound(s), in particular sulfites and/or bisulfite antioxidants.
  • compositions further comprising at least one sulfur-containing antioxidant compounds are provided.
  • Such compounds function as antioxidants in the invention compositions and, thus, are preferably added in antioxidant effective amounts.
  • Suitable sulfur-containing antioxidant compounds for use in the invention compositions include, but are not limited to, alkali metal or alkaline-earth metal (or ammonium) sulfites and/or bisulfites such as potassium sulfite, sodium sulfite, potassium bisulfite, sodium bisulfite, potassium metabisulfite, and sodium metabisulfite, and substituted or unsubstituted sulfur-containing amino acids such as, for example, cysteine, methionine, and taurine, and substituted derivatives thereof such as N-acetyl cysteine and cysteine hydrochloride, glutathione, and mixtures thereof.
  • alkali metal or alkaline-earth metal (or ammonium) sulfites and/or bisulfites such as potassium sulfite, sodium sulfite, potassium bisulfite, sodium bisulfite, potassium metabisulfite, and sodium metabisulfite
  • the compositions of the invention comprise sulfur-containing antioxidant(s) in an amount ranging from about 0.0001 to about 0.5%, preferably from about 0.0005 to about 0.1%, preferably from about 0.001 to about 0.075%, and preferably from about 0.002 to 0.05%, by weight, based on the total weight of the composition, including all ranges and subranges therebetween such as, for example, 0.1 to 0.3%, 0.02 to 0.075%, 0.075 to 0.25%, etc.
  • the antioxidant component of the compositions of the present invention consists essentially of, or consists of, sulfur-containing antioxidant(s).
  • the antioxidant component of the composition is “free of,” “devoid of’ or “substantially free of’ antioxidants other than sulfur-containing antioxidant(s), in particular ascorbic acid compounds such as ascorbic acid and ester(s) of ascorbic acid.
  • 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)e — 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 water-soluble or water-dispersible in neutralized form.
  • the amphiphilic polymers may be crosslinked.
  • the crosslinking agents may be chosen from, for example, the polyolefmically 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 lysine, 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 lysine, 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
  • POLYACRYLDIMEHYLTAURAMIDE 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 Ci6 alkanes such as Cs to Ci6 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?
  • Purcellin oil cetostearyl octanoate
  • isononyl isononanoate C12 to Cis alkyl benzoate
  • isopropyl myristate 2-ethylhexyl palmitate
  • octanoates decanoates or ricinoleates of alcohols or of polyalcohols
  • hydroxylated esters for instance isostearyl lactate or dnsostearyl 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.
  • 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 such as poly(12-hydroxystearic acid), sunscreens, preserving agents, fragrances, fillers, 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 composition 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.
  • the composition in particular a setter composition for cosmetics, comprises (1) at least one polyphenol X comprising at least two different phenol groups, (2) at least one (poly)glycerolated and/or poly oxy alkylenated 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 (li) 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 chelating agent and at least one ascorbic acid compound to the composition during preparation of the composition in an amount sufficient to stabilize the polyphenol X with respect to reducing aggregation as defined above in the composition are provided.
  • the amount of the at least one chelating agent and at least one ascorbic acid compound comprises adding at least one chelating agent and at least one ascorbic
  • compositions in particular a setter composition for cosmetics, comprises adding (1) at least one nonionic compound Y which is a surfactant having ahydrophihc-lipophihc balance (HLB) greater than or equal to 7, has at least one carbon chain having at least 8 carbon atoms, and has at least one (poly)glycerolated chain and/or polyoxyalkylenated chain and (2) 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, to the composition during preparation of the composition
  • HLB hydrophilophihc-lipophihc balance
  • compositions in particular a setter composition for cosmetics, comprises (1) at least one polyphenol X comprising at least two different phenol groups, (2) at least one (poly)glycerolated and/or poly oxy alkylenated 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 (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, wherein the method comprises adding at least one sulfur-containing antioxidant to the composition during preparation of the composition in an amount sufficient to stabilize the polyphenol X with respect to reducing aggregation as defined above in the composition are provided.
  • the amount of the at least one sulfur-containing antioxidant added to the composition during preparation of the composition to stabilize the polyphenol is
  • 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; (4) optionally at least one chelating agent; and (5) optionally at least one antioxidant selected from the group consisting of at least one ascorbic acid compound, at least one sulfur-containing antioxidant, and mixtures thereof; and (B) at least one other composition such as a color coat composition comprising at least one colorant are provided.
  • a composition in particular a setter composition for cosmetics, comprising (1)
  • 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 formation of a precipitate of compound X and compound Y in the composition prior to application; (4) optionally at least one chelating agent; and (5) optionally at least one antioxidant selected from the group consisting of
  • compositions containing chelating agent and ascorbic acid compound were formulated by mixing the ingredients in following Table
  • a composition such as that from Example 1A is placed into a 45°C oven for 4 weeks or 8 weeks.
  • the composition is visually observed for aggregation in the composition.
  • Visual aggregation within the composition indicates composition instability.
  • a composition such as that from Example 1A is placed into a 45°C oven for 4 weeks or 8 weeks. Color can be evaluated upon removal from the oven.
  • compositions containing different antioxidants and/or chelating agents can be compared to determine color differences, with lighter colors indicating better composition stability, in particular better polyphenol X stability within the composition. In this way, the effect on composition stability, in particular polyphenol X stability, of different antioxidants and/or chelating agents can be determined.
  • colorimetry analysis can be performed to more quantitatively determine composition color and thus composition stability, in particular polyphenol X stability within the composition.
  • the composition can be deposited on white cards, coating the white card with a thickness of 6 mils.
  • a color spectrometer can be used to determine the color value of areas of the white card with or without the deposit (or coating). The color for both areas can be recorded using L, a, b values as is known in the art. Color difference values AE can be calculated using differences in L, a, and b values in the white and coated/deposited areas of the card as follows:
  • compositions were prepared in accordance with the Table in Example 1A above. These compositions were placed into a 45°C oven for period of 4 weeks and 8 weeks. AE values were determined as described above.
  • compositions containing both chelating agent and ascorbic acid compounds were substantially more stable than compositions lacking both ingredients.
  • Invention Composition 1 and 2 contained ascorbyl glucoside and chelator, and both had limited color changes and had no visible aggregations.
  • Invention Composition 3 contained ascorbic acid and chelator. It was a darker composition (red) indicating that Vitamin C does not provide as much color stability to compositions as esters of ascorbic acid, which was a surprising additional benefit of the esters of ascorbic acid. However, it did prevent aggregation of polyphenol compound X as described above.
  • Comparative composition 1 did not contain any chelating agent or ascorbic acid compound. It contained visible aggregations at both 4 weeks and 8 weeks. Also, an increase of aggregates in size and number in 8 weeks versus 4 week was observed. With brown aggregates increased, the film deposit (coating) lost consistency for accurate and lower color readings.
  • Comparative composition 2 contained niacinamide instead of ascorbic acid compound. It did contain chelating agent. It only slightly improved inhibition of color darkening properties, and aggregations were formed.
  • compositions of the invention containing ascorbyl glucoside and chelating agent were noticeably lighter in color and did not contain visual aggregations, indicating better stability of polyphenol X.
  • Example IIA Sample Formulations Containing Sulfur-Containing Antioxidant
  • compositions containing sulfur-containing antioxidant were formulated by mixing the ingredients in the following Table.
  • a composition such as one from Example IIB is placed into a 45°C oven for 4 weeks or 8 weeks.
  • the composition is visually observed for aggregation in the composition.
  • Visual aggregation within the composition indicates composition instability.
  • a composition such as one from Example IIB is placed into a 45°C oven 4 weeks or 8 weeks. Color can be evaluated after removal of the samples from the oven at the desired time interval.
  • compositions containing different antioxidants and/or sulfur-containing antioxidants can be compared to determine color differences, with lighter colors indicating better composition stability, in particular better polyphenol X stability within the composition. In this way, the effect on composition stability, in particular polyphenol X stability, of different antioxidants and/or sulfur-containing antioxidants can be determined.
  • composition stability in particular polyphenol X stability within the composition.
  • the composition can be deposited on white cards, coating the white card with a thickness of 6 mils. After a set amount of time to allow the deposit (or coating) to dry (for example, 1-4 hours), a color spectrometer can be used to determine the color value of areas of the white card with or without the deposit (or coating). The color for both areas can be recorded using L, a, b values as is known in the art.
  • Color difference values AE can be calculated using differences in L, a, and b values as is known in the art.
  • Color difference values AE can be calculated using differences in L, a, and b values in the white and coated/deposited areas of the card as follows:
  • Comparative compositions 1 and 2 did not contain any sulfur-containing antioxidant. They were dark compositions and contained aggregations after 4 weeks and the number and size for the aggregates increased after 8 weeks.
  • Invention Compositions did not contain aggregations upon visual inspection after 4 weeks.
  • Invention Composition 2 turned dark after 8 weeks, and started showing some visible aggregates.
  • Invention Composition 1 and 3 still had light color after 8 weeks and did not contain visible aggregates.
  • Example IIIA Sample Formulations
  • Example IIIB Preparation Of Compositions Containing High HLB Value Surfactant As
  • compositions falling within the preferred ranges for ingredients in the Table in example IIIA were prepared.
  • a cosmetic product e.g., foundation
  • keratinous material e.g., skin
  • a controlled amount e.g., 0.020 gram
  • a controlled area e.g., 3 cm x 3 cm square
  • the makeup (e.g. foundation) quality/alteration is evaluated visually before and after applying the composition (setter).
  • a white cotton ball or pad is used to mb across the area a pre-determined number of times (for example, for 5 times) to assess transfer resistance of cosmetic composition to the cotton ball or pad.
  • Transfer resistance is evaluated by determining the difference in cosmetic composition transferred to the cotton ball or pad, with or without the applied setting composition.
  • Example 1IIB For the comparative examples in Example 1IIB, higher C2-C5 monoalcohol levels were needed to inhibit precipitate formation. As a result, composition homogeneity was affected, resulting in unacceptable alteration/change of previously-applied foundation to which the comparative compositions had been applied. Contrary to the comparative compositions, the invention compositions inhibited precipitate formation in formulation with lower alcohol level and resulted in better makeup characteristics when applied to previously-applied foundation.
  • Comparative example 1 level 4, with makeup shift
  • Comparative example 3 level 3, with makeup shift Comparative example 4: level 3, with makeup shift Invention example 1: level 4 Invention example 2: level 3 Invention example 3: level 3 Invention example 4: level 4 Invention example 5: level 4 Invention example 6: level 4
  • Invention example 7 level 5, lowest transfer

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  • Veterinary Medicine (AREA)
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  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des compositions, en particulier des compositions de consigne 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 ; (4) éventuellement au moins un agent chélatant ; et (5) éventuellement au moins un antioxydant choisi dans le groupe constitué par au moins un composé d'acide ascorbique, au moins un antioxydant contenant du soufre et des mélanges de ceux-ci, ainsi que des procédés, des kits et des ensembles comprenant de telles compositions dans un ou plusieurs récipients ou dans une application.
PCT/US2023/020481 2022-04-28 2023-04-28 Compositions de fixation WO2023212368A1 (fr)

Applications Claiming Priority (12)

Application Number Priority Date Filing Date Title
US17/731,712 US20230346657A1 (en) 2022-04-28 2022-04-28 Compositions suitable as setters
US17/731,759 US20230346662A1 (en) 2022-04-28 2022-04-28 Compositions suitable as setters
US17/731,712 2022-04-28
US17/731,816 US20230346664A1 (en) 2022-04-28 2022-04-28 Compositions suitable as setters
US17/731,759 2022-04-28
US17/731,816 2022-04-28
FR2206834A FR3137565A1 (fr) 2022-07-05 2022-07-05 Compositions convenables comme fixateurs
FR2206833A FR3137572A1 (fr) 2022-07-05 2022-07-05 Compositions appropriées comme fixateurs
FRFR2206834 2022-07-05
FR2206839A FR3134975A1 (fr) 2022-04-28 2022-07-05 Compositions appropriées comme fixateurs
FRFR2206839 2022-07-05
FRFR2206833 2022-07-05

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US20040170586A1 (en) 2002-06-12 2004-09-02 L'oreal Cosmetic composition containing a polyorganosiloxane polymer
CA2649412A1 (fr) 2006-04-20 2007-11-01 M-I Llc Gels aqueux pour le renforcement de forages de puits
JP2007314483A (ja) * 2006-05-29 2007-12-06 Ichimaru Pharcos Co Ltd 外用製剤並びに外用製剤の製造方法
CN104971200A (zh) 2015-07-10 2015-10-14 浙江红雨医药用品有限公司 一种鞣酸ph稳定型痔疮凝胶及其制备方法
CN108175765A (zh) 2017-12-01 2018-06-19 东南大学 一种酸敏控释抗炎凝胶及其制备方法与应用
US20200268633A1 (en) * 2019-02-25 2020-08-27 Jonathan Joseph Petrillo Skin treatment
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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US20040170586A1 (en) 2002-06-12 2004-09-02 L'oreal Cosmetic composition containing a polyorganosiloxane polymer
CA2649412A1 (fr) 2006-04-20 2007-11-01 M-I Llc Gels aqueux pour le renforcement de forages de puits
US8377853B2 (en) 2006-04-20 2013-02-19 M-I L.L.C. Aqueous gels for well bore strengthening
JP2007314483A (ja) * 2006-05-29 2007-12-06 Ichimaru Pharcos Co Ltd 外用製剤並びに外用製剤の製造方法
CN104971200A (zh) 2015-07-10 2015-10-14 浙江红雨医药用品有限公司 一种鞣酸ph稳定型痔疮凝胶及其制备方法
CN108175765A (zh) 2017-12-01 2018-06-19 东南大学 一种酸敏控释抗炎凝胶及其制备方法与应用
US20200268633A1 (en) * 2019-02-25 2020-08-27 Jonathan Joseph Petrillo Skin treatment
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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"Kirk Othmer Encyclopedia of Chemical Technology", vol. 5, 2003, article "Chelating agents", pages: 708 - 739
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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