WO2021021978A1 - Compositions contenant un copolymère de vinylpyrrolidone et d'acide acrylique et agent de formation de film - Google Patents

Compositions contenant un copolymère de vinylpyrrolidone et d'acide acrylique et agent de formation de film Download PDF

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Publication number
WO2021021978A1
WO2021021978A1 PCT/US2020/044146 US2020044146W WO2021021978A1 WO 2021021978 A1 WO2021021978 A1 WO 2021021978A1 US 2020044146 W US2020044146 W US 2020044146W WO 2021021978 A1 WO2021021978 A1 WO 2021021978A1
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Prior art keywords
composition
present
vinylpyrrolidone
compositions
acrylic acid
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PCT/US2020/044146
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English (en)
Inventor
I-Fan Hsieh
Ramakrishnan Hariharan
Charles Ward
Original Assignee
L'oreal
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Filing date
Publication date
Priority claimed from US16/527,675 external-priority patent/US11878067B2/en
Priority claimed from US16/527,632 external-priority patent/US20210030636A1/en
Application filed by L'oreal filed Critical L'oreal
Publication of WO2021021978A1 publication Critical patent/WO2021021978A1/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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/042—Gels
    • 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
    • A61K8/85—Polyesters
    • 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
    • A61K8/88—Polyamides
    • 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

  • the present invention relates to compositions comprising at least one copolymer of vinylpyrrolidone and acrylic acid and at least one film forming agent.
  • compositions comprising at least one copolymer of vinylpyrrolidone and acrylic acid and at least one film forming agent.
  • these compositions have surprisingly good properties including transfer-resistance and oil-resistance.
  • these compositions have surprisingly good properties including transfer-resistance and playtime properties, as well as good anti-pilling properties when used as a primer composition.
  • US 9,655,836 discloses using anionic crosslinked rheology-modifying polymers with high molecular weight charged polymers.
  • US 2011/0097289 discloses polyurethane dispersions for decorative cosmetics which may include thickeners.
  • EP 2468238 discloses hair fixative that lists numerous polymers for possible inclusion but which requires silicone wax and propellant and does not contain coloring agent.
  • EP 2234583 discloses compositions containing solid microspheres.
  • US 9,126,303 discloses a mascara primer containing polyquat-69.
  • US 2016/0000687 discloses cosmetic compositions containing polyester/polyurethanes.
  • one aspect of the present invention is a care and/or makeup and/or treatment composition for keratinous materials which has good cosmetic properties such as, for example, good transfer-resistance and oil- resistance, particularly a composition containing a coloring agent.
  • one aspect of the present invention is a care and/or makeup and/or treatment composition for keratinous materials which has good cosmetic properties such as, for example, good transfer-resistance and playtime properties, particularly a primer composition.
  • the present invention relates to compositions comprising at least one copolymer of vinylpyrrolidone and acrylic acid and at least one film forming agent.
  • the present invention relates to gel compositions comprising at least one copolymer of vinylpyrrolidone and acrylic acid, at least one film forming agent, and at least one coloring agent.
  • the present invention relates to emulsion compositions comprising at least one polymer including imide group(s), at least one humectant, and at least one copolymer of vinylpyrrolidone and acrylic acid.
  • the composition is an oil- in-water (O/W) emulsion.
  • the compositions are free of colorants, and when free of colorants, preferably are in the form of a primer composition.
  • the present invention also relates to colored emulsion compositions comprising at least one colorant, at least one polymer including imide group, at least one humectant, and at least one copolymer of vinylpyrrolidone and acrylic acid.
  • the composition is an oil-in-water (O/W) emulsion.
  • the present invention also relates to methods of treating, caring for and/or making up keratinous materials by applying compositions of the present invention to a keratinous material in an amount sufficient to treat, care for and/or make up the keratinous material.
  • the present invention also relates to methods of enhancing the appearance of keratinous materials by applying compositions of the present invention to a keratinous material in an amount sufficient to enhance the appearance of the keratinous material.
  • the present invention also relates to methods of treating, caring for and/or making up keratinous materials by applying gel compositions of the present invention to a keratinous material in an amount sufficient to treat, care for and/or make up the keratinous material.
  • the present invention also relates to methods of enhancing the appearance of keratinous materials by applying gel compositions of the present invention to a keratinous material in an amount sufficient to enhance the appearance of the keratinous material.
  • the present invention also relates to methods of treating, caring for and/or making up keratinous materials by applying emulsion compositions of the present invention to a keratinous material in an amount sufficient to treat, care for and/or make up the keratinous material.
  • the present invention also relates to methods of enhancing the appearance of keratinous materials by applying emulsion compositions of the present invention to a keratinous material in an amount sufficient to enhance the appearance of the keratinous material.
  • the present invention also relates to methods of enhancing the appearance of keratinous materials by a primer composition to a keratinous material, and then applying a gel composition of the present invention to the primer
  • composition in an amount sufficient to enhance the appearance of the keratinous material.
  • the present invention also relates to methods of enhancing the appearance of keratinous materials by applying emulsion compositions of the present invention to a keratinous material, and then applying a colored cosmetic composition to the compositions of the present invention in an amount sufficient to enhance the appearance of the keratinous material.
  • the expression “at least one” means one or more and thus includes individual components as well as mixtures/combinations.
  • Film former or“film forming agent” as used herein means any material such as, for example, a polymer or a resin that leaves a film on the substrate to which it is applied.
  • Polymer as used herein means a compound which is made up of at least two monomers.
  • Keratinous materials includes materials containing keratin such as hair, skin, eyebrows, lips and nails.
  • “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, acyloxyalkyl 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, hydroxyalkyl 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.
  • Long wear compositions refers to compositions where the compositions, after application to a keratinous material, do not transfer or smudge after contact with another substrate and retain a consistent appearance on the keratinous material for an extended period of time.
  • Long wear compositions can also refer 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.
  • Long wear properties may be evaluated 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 keratinous materials such as skin, eyelashes or lips and evaluating the color of the composition after an extended period of time.
  • the color of a composition may be evaluated immediately following application to the keratinous material 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. Additionally, long wear properties may be evaluated by applying a sample, allowing it to dry, and then abrading the sample to determine removal/loss of sample.
  • Transfer refers to the displacement of a fraction of a composition which has been applied to a keratinous material by contact with another substrate, whether of the same nature or of a different nature.
  • a composition such as an eyeshadow, eyeliner or mascara
  • the composition can be transferred onto hands by rubbing or by contact of the hands with the eyes.
  • a composition such as a lipstick
  • the composition can be transferred onto teeth or hands, or onto the cheek of another person.
  • the composition can also transfer from the keratinous material to which if has been applied to another substrate such as napkins, collars, glasses, cups or other containers.
  • Transfer-resistance refers to the quality exhibited by a composition in resisting transfer.
  • the amount of composition transferred from a keratinous material to a substrate may be evaluated and compared.
  • a composition may be transfer-resistant if, after application to a keratinous material such as lips, skin or eyelashes and contact with a substrate, a majority of the composition is left on the wearer. Further, the amount transferred may be compared with that transferred by other compositions, such as commercially-available compositions. In a preferred embodiment of the present invention, little or no composition is transferred to the substrate from the keratinous material.
  • Oil-resistance or“sebum-resistance” as used herein means transfer resistance when the composition contacts oil or sebum, respectively.
  • Gel Crossover 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: a Discovery HR-2 Rheometer by TA Instruments can be used, 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 % 0.1 to 1000.0%. 5 points per decade.
  • Playtime as used herein relates to how the formula spreads upon application to keratinous material (e.g., skin) and the amount of time it takes to spread upon application. It also relates to the amount of time it takes for the formula to be absorbed into keratinous material (e.g., skin).
  • pilling refers to accumulation or agglomeration of materials (“balling up” or“pilling up”) from a composition on a keratinous material during application of a composition on the keratinous material.
  • the composition of the present invention may be in any form, either liquid or non-liquid (semi-solid, soft solid, solid, etc.).
  • it may be a paste, a solid, or a cream.
  • It may be an oil-in-water or water-in-oil emulsion, a multiple emulsion, such as an oil-in-water-in-oil emulsion or a water-in-oil-in-water emulsion.
  • the composition of the invention may, for example, comprise an external or continuous fatty phase.
  • the composition can also be a molded composition or cast as a stick or a dish.
  • 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 in personal care.
  • gel compositions comprising at least one copolymer of vinylpyrrolidone and acrylic acid, at least one film forming agent, and at least one coloring agent are provided.
  • gel compositions of the present invention have a gel crossover point ranging from about 2% to about 50% strain, preferably from about 3% to about 40% strain, and preferably from about 4% to about 30% strain, including all ranges and subranges therebetween.
  • emulsion compositions comprising water, at least one polymer including imide group(s), at least one humectant, and at least one copolymer of vinylpyrrolidone and acrylic acid are provided.
  • compositions comprising at least one copolymer of vinylpyrrolidone and acrylic acid are provided.
  • Suitable copolymers are described, for example, in U.S. patents 7,799,321 and 7,205,271 , the entire contents of both of which are hereby incorporated by reference.
  • the copolymer is crosslinked.
  • Suitable crosslinkers have at least two free radical polymerizable groups in the molecule, e.g. pentaerythritol trial lylether, pentaerythritol triacrylate, pentaerythritol tetraacrylate or methylene bisacrylamide.
  • the copolymer is linear.
  • the copolymer comprises about 10-90 wt. % of vinyl pyrrolidone and about 10-90 wt. % of acrylic acid, including all ranges and subranges there between. So, for example, copolymers could include 10%-50% vinylpyrrolidone and 50%-90% acrylic acid; 40%-80% vinylpyrrolidone and 20%-60% acrylic acid; 25%-75% vinylpyrrolidone and 25%-75% acrylic acid; 55%- 85% vinylpyrrolidone and 15%-45% acrylic acid; 30%-60% vinylpyrrolidone and 40%-70% acrylic acid, etc.
  • a suitable example of a commercially-available copolymer of vinylpyrrolidone and acrylic acid is UltrathixTM P-100 available from Ashland
  • the copolymer of vinylpyrrolidone and acrylic acid is preferably present in the compositions of the present invention in an active solid content amount ranging from greater than 0.1 % to about 20%, preferably from greater than 0.5% to about 10%, and preferably from about 1 % to about 5%, by weight with respect to the total weight of the composition, including all ranges and subranges there between, such as 1 -10%, 2-8%, 1-6%, etc.
  • compositions comprising at least one film forming agent are provided.
  • Suitable film forming agents include, for example, Si-based film forming agents such as silicone resins, silicone acrylate compounds, silicone elastomer resins, and dendritic silicone acrylates.
  • suitable silicone resins include, for example, MQ resins (for example, trimethylsiloxysilicates), T-propyl silsesquioxanes and MK resins (for example, polymethylsilsesquioxanes), silicone esters such as those disclosed in U.S. Pat. Nos. 6,045,782, 5,334,737, and 4,725,658, the disclosures of which are hereby incorporated by reference.
  • MQ resins for example, trimethylsiloxysilicates
  • T-propyl silsesquioxanes for example, polymethylsilsesquioxanes
  • silicone esters such as those disclosed in U.S. Pat. Nos. 6,045,782, 5,334,737, and 4,725,658, the disclosures of which are hereby incorporated by reference.
  • Silicone acrylate compounds include polymers comprising a backbone chosen from vinyl polymers, methacrylic polymers, and acrylic polymers and at least one chain chosen from pendant siloxane groups and pendant fluorochemical groups such as those disclosed in U.S. Pat. Nos. 5,209,924,
  • Suitable silicone elastomer resins include, for example, compounds which comprise a“silicone elastomer” portion and a“resin” portion. Silicone elastomer resins are described or referenced in U.S. patents 8,987,373 and
  • Suitable dendritic silicone acrylates copolymers include, for example, branched polymers comprising at least one siloxane group and at least one hydrocarbon group.
  • Specific examples of suitable dendritic silicone acrylate copolymers include the acrylate/dimethicone copolymers sold by Dow Corning under the tradenames FA 4001 CM SILICONE ACRYLATE (cyclopentasiloxane (and) acrylates/polytrimethylsiloxymethacrylate copolymer), FA 4002 ID SILICONE ACRYLATE (isododecane (and) acrylates/polytrimethylsiloxymethacrylate
  • the film forming agent is selected from the group consisting of (1 ) polymers including imide group(s), (2) low molecular weight sulfopolyester compounds, and (3) mixtures thereof.
  • (1 ) polymers including imide group(s), (2) low molecular weight sulfopolyester compounds, and (3) mixtures thereof will be discussed below.
  • the copolymer of vinylpyrrolidone and acrylic acid can possess film forming properties as well.
  • the polymer including imide group(s) is selected from the group consisting of alkylmaleimides, polysuccinimides, and hydroxyalkylmaleimides.
  • suitable polymers include polymers containing repeating units of alpha-olefin N-alkylmaleimide or alpha-olefin N- hydroxyalkylmaleimide, a specific example of which is
  • polyimide-1 isobutylene/ethylmaleimide/hydroxyethylmaleimide copolymer
  • Polyimide-1 which is available in a commercial product sold under the name Aquaflex®FX-64 (30% active solid content in water).
  • Polysuccinimide sold under the name Rhodomer PSI, polysuccinimide partially (50%) modified, and polyisobutylene succinimide sold under the name Flostacerin PIB are other examples of acceptable polymers.
  • the copolymer of vinylpyrrolidone and acrylic acid and the polymer including imide group(s) are present in the compositions of the present invention in an active solid content weight ratio of less than or equal to 1.25: 1 , preferably less than or equal to 1 :1 , preferably less than or equal to 0.8:1 , and preferably less than or equal to 0.6:1 , including all ranges and subranges therebetween, such as, for example, 0.1 :1 to 0.9:1 , 0.5:1 to 1.25:1 , etc.
  • the weight amount of polymer including imide group(s) present in the compositions of the present invention is greater than the weight amount of copolymer of vinylpyrrolidone and acrylic acid.
  • the polymer including imide group(s) when the composition is an emulsion composition, preferably is present in the compositions of the present invention in an active solid content amount ranging from about 0.1 % to about 20%, preferably from about 0.5% to about 10%, and preferably from about 1 % to about 5%, by weight with respect to the total weight of the composition, including all ranges and subranges there between, such as 1 -10%, 2-8%, 1 -6%, etc.
  • “sulfopolyester compound” means a polymeric compound made from glycol(s), aromatic diacid(s), phthalic acid(s) and neutralized phthalic acid sulfonates.
  • the sulfopolyester compound may be made from additional monomers in addition to the four identified monomers - that is, the sulfopolyester compound may“comprise” the four identified monomers, or it may“consist essentially of” the four identified monomers.
  • the sulfopolyester compound may also “consist of” only the four identified monomers.
  • Suitable glycols include, but are not limited to, alkylene glycols and diglycols such as ethylene glycol, propylene glycol, ethylene diglycol and propylene diglycol.
  • Suitable aromatic diacids include, but are not limited to, cyclohexanedialkanols such as, for example, cyclohexanedimethanol,
  • cyclohexanediisobutanol, etc. and cyclopentanedialkanols such as, for example, cyclopentanedimethanol, cyclopentanediethanol, etc.
  • Suitable phthalic acids include, but are not limited to, isophthalic acid and terephthalic acid.
  • Suitable neutralized phthalic acid sulfonates include, but are not limited to, alkali isophthalic acid sulfonates such as sodium isophthalic acid sulfonates, potassium isophthalic acid sulfonates, etc., and alkali terephthalic acid sulfonates such as sodium terephthalic acid sulfonate and potassium terephthalic acid sulfonate.
  • low molecular weight means less than 75,000 Da weight average molecular weight, preferably less than 60,000 Da, preferably less than 50,000 Da, and preferably less than 40,000 Da, including all ranges and subranges therebetween.
  • the low molecular weight sulfopolyester compound is polyester-1 or polyester-5, a diethylene
  • glycol/phthalate/isophthalate/1 ,4-cyclohexanedimethanol copolymer sold under the names Eastman AQ polymer (AQ35S, AQ38S, AQ55S, AQ48 Ultra) by the company Eastman Chemical.
  • the film forming agent is preferably a low molecular weight
  • compositions of the present invention in an active solid content amount ranging from about 0.1 % to about 20%, preferably from about 0.2% to about 10%, preferably from about 0.25% to about 5%, and preferably from about 0.33% to about 3%, by weight with respect to the total weight of the composition, including all ranges and subranges there between, such as 1 -10%, 2- 8%, 1 -6%, etc.
  • the film forming agent is preferably present in the compositions of the present invention in an active solid content amount ranging from about 0.1 % to about 20%, preferably from about 0.2% to about 10%, preferably from about 0.25% to about 5%, and preferably from about 0.33% to about 3%, by weight with respect to the total weight of the composition, including all ranges and subranges there between, such as 1 -10%, 2-8%, 1 -6%, etc.
  • vinylpyrrolidone and acrylic acid and the film forming agent are present in the compositions of the present invention in an active solid content weight ratio of greater than or equal to 1 :1 , preferably greater than or equal to 1.5:1 , preferably greater than or equal to 2:1 , and preferably greater than or equal to 3:1 , including all ranges and subranges therebetween, such as, for example, 1 :1 to 10:1 , 2:1 to .7:1 ; and 1.5:1 to 4:1 , etc.
  • the weight amount of copolymer of vinylpyrrolidone and acrylic acid present in the compositions of the present invention is greater than the weight amount of film forming agent.
  • compositions comprising at least one humectant are provided.
  • Humectants and their properties are well-known to those in the art.
  • Suitable humectants include, but are not limited to, polyhydric alcohols such as, for example, C 2 -C 8 and preferably C 3 -C 6 compounds comprising from 2 to 6 hydroxyl radicals, such as glycerol, propylene glycol, tripropylene glycol, 1 ,3-butylene glycol, dipropylene glycol or diglycerol, and a mixture thereof, sugars such as sorbitol or xylitol, hyaluronic acid and salts thereof, hyaluronic acid spheres such as those sold by the company Engelhard Lyon, urea and derivatives thereof such as hydroxyethyl urea, especially Hydrovance (2-hydroxyethylurea) sold by National Starch, sodium pido
  • Preferred humectants are selected from the group consisting of glycol compounds, urea derivatives, and mixtures thereof, in particular propylene glycol, tripropylene glycol, 1 ,3-butylene glycol, dipropylene glycol, and hydroxyethyl urea.
  • the humectant is preferably present in the compositions of the present invention in an amount greater than or equal to 10%, preferably in an amount greater than or equal to 12%, preferably in an amount greater than or equal to 15%, and preferably in an amount greater than or equal to 20%, by weight with respect to the total weight of the composition, including all ranges and subranges there between, such as 10-50%, 12-60%, 15-25%, 10-25%, etc.
  • one aspect of the present invention is providing a playtime improving effective amount of humectant to compositions containing polymer including imide group(s) and copolymer of vinylpyrrolidone and acrylic acid.
  • compositions further comprising at least one coloring agent are provided.
  • the coloring agent is preferably chosen from pigments, dyes, such as liposoluble dyes or water-soluble dyes, nacreous pigments, glitter and pearlescent pigments.
  • Representative liposoluble dyes which may be used according to the present invention include Sudan Red, DC Red 17, DC Green 6, b-carotene, soybean oil, Sudan Brown, DC Yellow 11 , DC Violet 2, DC Orange 5, annatto, and quinoline yellow.
  • the liposoluble dyes when present, generally have a concentration ranging up to 40% by weight of the total weight of the composition, such as from 0.0001 % to 30%, including all ranges and subranges therebetween.
  • the nacreous pigments which may be used according to the present invention may be chosen from 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 nacreous pigments if present, be present in the composition in a concentration ranging up to 50% by weight of the total weight of the composition, such as from 0.0001 % to 40%, preferably from 0.001 % to 30%, including all ranges and subranges therebetween.
  • Pigments may be chosen from white, colored, inorganic, organic, polymeric, and nonpolymeric pigments.
  • mineral pigments include titanium dioxide, zirconium oxide, zinc oxide, cerium oxide, iron oxides, chromium oxides, manganese violet, ultramarine blue, chromium hydrate, and ferric blue.
  • organic pigments include carbon black, pigments of D & C type, and lakes based on cochineal carmine, barium, strontium, calcium, and aluminum.
  • the coloring agents (colorants), if present, are preferably present in the compositions of the present invention in a concentration ranging up to 50 % by weight of the total weight of the composition, such as from 1 % to 40%, and further such as from 5% to 30%, including all ranges and subranges therebetween such as, for example, 2-25%, 5-35%, 10-40%, etc.
  • compositions of the present invention are in emulsion form, the compositions comprise little or no colorant.
  • compositions of the present invention contain little or no colorant
  • the composition is in the form of a primer composition to be applied between keratinous material and a colored cosmetic composition containing colorant.
  • compositions of the present invention preferably contain less than 0.1 % colorant.
  • compositions of the present invention preferably contain less than 0.05% colorant.
  • compositions of the present invention preferably contain less than 0.01 % colorant.
  • compositions of the present invention also contain water.
  • Water is preferably present in an amount of from about 10% to about 80% by weight, preferably from about 20% to about 70% by weight, preferably from about 35% to about 65% by weight, including all ranges and subranges therebetween, all weights being based on the total weight of the composition.
  • compositions of the present invention contain water, and are in the form of an oil-in-water emulsion (O/W) or a water-in-oil emulsion (W/O). Particularly preferred compositions are in the form of an oil-in-water emulsion.
  • compositions further comprising at least one fatty substance are provided.
  • Suitable fatty substances include oil(s) and/or wax(es).
  • Oil means any non-aqueous medium which is liquid at ambient temperature (25°C) and atmospheric pressure (760 mm Hg).
  • a "wax” for the purposes of the present disclosure 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, which can be as high as 150°C, a hardness of more than 0.5 MPa at ambient temperature, and an anisotropic crystalline organization in the solid state.
  • Suitable oils include volatile and/or non-volatile oils.
  • Such oils can be any acceptable oil including but not limited to silicone oils and/or hydrocarbon oils.
  • the compositions of the present invention preferably comprise one or more 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
  • 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 have a flash point of at least 40°C.
  • a volatile linear silicone oil may be employed in the present invention.
  • Suitable volatile linear silicone oils include those described in U.S. patent no. 6,338,839 and W003/042221 , the contents of which are incorporated herein by reference.
  • the volatile linear silicone oil is
  • decamethyltetrasiloxane In another embodiment, the decamethyltetrasiloxane is further combined with another solvent that is more volatile than
  • the composition of preferably comprises one or more non-silicone volatile oils and may be selected from volatile hydrocarbon oils, volatile esters and volatile ethers.
  • volatile non-silicone oils include, but are not limited to, volatile hydrocarbon oils having from 8 to 16 carbon atoms and their mixtures and in particular branched C 8 to Ci 6 alkanes such as C 8 to Ci 6 isoalkanes (also known as isoparaffins), isohexadecane, 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.
  • Non-limiting examples of volatile non-silicone volatile oils are given in Table 2 below.
  • the volatility of the solvents/oils can be determined using the evaporation speed as set forth in U.S. patent no. 6,338,839, the contents of which are incorporated by reference herein.
  • the composition comprises at least one non-volatile oil.
  • non-volatile oils that may be used in the present invention include, but are not limited to, polar oils such as: [00108] - hydrocarbon-based plant oils with a high triglyceride content consisting of fatty acid esters of glycerol, the fatty acids of which may have varied chain lengths, these chains possibly being linear or branched, and saturated or unsaturated; these oils are especially wheat germ oil, corn oil, sunflower oil, karite butter, castor oil, sweet almond oil, macadamia oil, apricot oil, soybean oil, rapeseed oil, cottonseed oil, alfalfa oil, poppy oil, pumpkin oil, sesame seed oil, marrow oil, avocado oil, hazelnut oil, grape seed oil, blackcurrant seed oil, evening primrose oil, millet oil, barley oil, quinoa oil, olive oil, rye oil, safflower
  • R 5 COOR 6 in which R 5 represents a linear or branched higher fatty acid residue containing from 1 to 40 carbon atoms, including from 7 to 19 carbon atoms, and R 6 represents a branched hydrocarbon-based chain containing from 1 to 40 carbon atoms, including from 3 to 20 carbon atoms, with R 6 + R 7 3 10, such as, for example, Purcellin oil (cetearyl octanoate), isononyl isononanoate, octyldodecyl neopentanoate, C 12 to C 15 alkyl benzoate, isopropyl myristate, 2-ethylhexyl palmitate, and octanoates, decanoates or ricinoleates of alcohols or of polyalcohols; hydroxylated esters, for instance isostearyl lactate or diisostearyl malate; and pentaerythrito
  • C 8 to C 26 fatty alcohols for instance oleyl alcohol, cetyl alcohol, stearyl alcohol, and cetearyl alcohol;
  • non-volatile oils examples include, but are not limited to, non-polar oils such as branched and unbranched hydrocarbons and hydrocarbon waxes including polyolefins, in particular Vaseline (petrolatum), paraffin oil, squalane, squalene, hydrogenated polyisobutene, hydrogenated polydecene, polybutene, mineral oil, pentahydrosqualene, and mixtures thereof.
  • non-polar oils such as branched and unbranched hydrocarbons and hydrocarbon waxes including polyolefins, in particular Vaseline (petrolatum), paraffin oil, squalane, squalene, hydrogenated polyisobutene, hydrogenated polydecene, polybutene, mineral oil, pentahydrosqualene, and mixtures thereof.
  • the at least one oil when present, is present in the compositions of the present invention in an amount ranging from about 0.5 to about 30% by weight, preferably from about 1 to about 10% by weight, and preferably from about 1 to about 5% by weight, based on the total weight of the composition, including all ranges and subranges within these ranges.
  • the at least one oil when present, is present in the compositions of the present invention in an amount ranging from about 5 to about 80% by weight, more preferably from about 10 to about 70% by weight, and most preferably from about 15 to about 60% by weight, based on the total weight of the composition, including all ranges and subranges within these ranges.
  • compositions of the present invention further comprise at least one wax.
  • Suitable examples of waxes that can be used in accordance with the present disclosure include those generally used in the cosmetics field: they include those of natural origin, such as beeswax, carnauba wax, candelilla wax, ouricoury wax, Japan wax, cork fibre wax or sugar cane wax, rice bran wax, rice wax, montan wax, paraffin wax, lignite wax or microcrystalline wax, ceresin or ozokerite, and hydrogenated oils such as hydrogenated castor oil or jojoba oil; synthetic waxes such as the polyethylene waxes obtained from the polymerization or copolymerization of ethylene, and Fischer-Tropsch waxes, or else esters of fatty acids, such as octacosanyl stearate, glycerides which are concrete at 30°C, for example at 45°C.
  • natural origin such as beeswax, carnauba wax, candelilla wax, ouricoury wax, Japan wax, cork fibre wax or sugar cane wax,
  • compositions of the present invention further include at least one silicone wax.
  • suitable silicone waxes include, but are not limited to, silicone waxes such as alkyl- or alkoxydimethicones having an alkyl or alkoxy chain ranging from 10 to 45 carbon atoms, poly(di)methylsiloxane esters which are solid at 30°C.
  • alkylated silicone acrylate copolymer waxes comprising at least 40 mole % of siloxy units having the formula (R 2 R'SiO 1/2 ) x (R"SiO 3/2 ) y , where x and y have a value of 0.05 to 0.95, R is an alkyl group having from 1 to 8 carbon atoms, an aryl group, a carbinol group, or an amino group, R is a monovalent hydrocarbon having 9-40 carbon atoms, R" is a monovalent hydrocarbon group having 1 to 8 carbon atoms, an aryl group such as those disclosed in U.S. patent application 2007/0149703, the entire contents of which is hereby incorporated by reference, with a particular example being C30-
  • the compositions of the present invention further include at least one long-chain alcohol wax.
  • the at least one long-chain alcohol wax has an average carbon chain length of between about 20 and about 60 carbon atoms, most preferably between about 30 and about 50 carbon atoms.
  • Suitable examples of long- chain alcohol waxes include but are not limited to alcohol waxes commercially available from Baker Hughes under the Performacol trade name such as, for example, Performacol 350, 425 and 550.
  • the long-chain alcohol wax has a melting temperature range from about 93°C to about 105°C.
  • the wax(es), if present may be present in an amount ranging from 0.5% to 10% by weight relative to the total weight of the composition, for example from 1 % to 10%, and for example from 1 % to 5%, including all ranges and subranges therebetween.
  • the wax(es), if present may be present in an amount ranging from 1 to 30% by weight relative to the total weight of the composition, for example from 2 to 20%, and for example from 3 to 10%, including all ranges and subranges therebetween.
  • compositions of the present invention contain less than 1 % wax and/or less than 1 % oil.
  • compositions of the present invention contain less than 0.5% wax and/or less than 0.5% oil.
  • compositions of the present invention contain no wax and/or oil.
  • composition of the invention can also comprise any additive usually used in the field under consideration.
  • dispersants such as poly(12-hydroxystearic acid), antioxidants, essential oils, sunscreens, preserving agents, fragrances, fillers such as cellulose fibers, neutralizing agents, cosmetic and dermatological active agents such as, for example, emollients, moisturizers, vitamins, essential fatty acids, surfactants, silicone elastomers, thickening agents, gelling agents, particles, pasty compounds, viscosity increasing agents can be added.
  • emollients such as, for example, emollients, moisturizers, vitamins, essential fatty acids, surfactants, silicone elastomers, thickening agents, gelling agents, particles, pasty compounds, viscosity increasing agents
  • 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).
  • additives may be present in the composition in a proportion from 0% to 99% (such as from 0.01 % to 90%) relative to the total weight of the composition and further such as from 0.1 % to 50% (if present), including all ranges and subranges therebetween.
  • composition of the invention should be cosmetically or dermatologically acceptable, i.e. , it should contain a non-toxic physiologically acceptable medium and should be able to be applied to the keratinous materials of human beings such as, for example, lips, skin or eyelashes.
  • suitable gelling agents for an oil phase include, but are not limited to, lipophilic or hydrophilic clays.
  • hydrophilic clay means a clay that is capable of swelling in water; this clay swells in water and forms after hydration a colloidal dispersion. These clays are products that are already well known per se, which are described, for example, in the book “Mineralogie des argiles", S. Caillere, S. Henin,
  • Clays are silicates containing a cation that may be chosen from calcium, magnesium, aluminium, sodium, potassium and lithium cations, and mixtures thereof. Examples of such products that may be mentioned include clays of the smectite family such as montmorillonites, hectorites, bentonites, beidellites and saponites, and also of the family of vermiculites, stevensite and chlorites. These clays may be of natural or synthetic origin.
  • Hydrophilic clays that may be mentioned include smectite products such as saponites, hectorites, montmorillonites, bentonites and beidellite. Hydrophilic clays that may be mentioned include synthetic hectorites (also known as laponites), for instance the products sold by the company Laporte under the names Laponite XLG, Laponite RD and Laponite RDS (these products are sodium
  • magnesium silicates and in particular sodium lithium magnesium silicates
  • lipophilic clay means a clay that is capable of swelling in a lipophilic medium; this clay swells in the medium and thus forms a colloidal dispersion.
  • lipophilic clays examples include modified clays such as modified magnesium silicate (Bentone Gel VS38 from Rheox), and hectorites modified with a C- 1 0 to C 22 fatty-acid ammonium chloride, for instance hectorite modified with distearyldimethylammonium chloride (CTFA name: disteardimonium hectorite) sold under the name Bentone 38 CE by the company Rheox or Bentone 38V® by the company Elementis.
  • modified clays such as modified magnesium silicate (Bentone Gel VS38 from Rheox), and hectorites modified with a C- 1 0 to C 22 fatty-acid ammonium chloride, for instance hectorite modified with distearyldimethylammonium chloride (CTFA name: disteardimonium hectorite) sold under the name Bentone 38 CE by the company Rheox or Bentone 38V® by the company Elementis.
  • CTFA name distearyldi
  • the silica particles are fumed silica particles.
  • Suitable silicas include, but are not limited to, hydrophobic silicas, such as pyrogenic silica optionally with hydrophobic surface treatment whose particle size is less than 1 micron, preferably less than 500 nm, preferably less than 100 nm, preferably from 5 nm to 30 nm, including all ranges and subranges therebetween . It is in fact possible to modify the surface of silica chemically, by a chemical reaction producing a decrease in the number of silanol groups present on the surface of the silica. The silanol groups can notably be replaced with
  • hydrophobic groups a hydrophobic silica is then obtained.
  • the hydrophobic groups can be:
  • Silicas treated in this way are called “Silica dimethyl silylate” according to the CTFA (6th edition, 1995). They are for example marketed under the references “AEROSIL R972®”, “AEROSIL R974®” by the company Degussa, "CAB-O-SIL TS-610®”, “CAB-O-SIL TS-720®” by the company Cabot.
  • silica aerogel particles can be added to compositions of the present invention, if desired.
  • Silica aerogels are porous materials obtained by replacing (by drying) the liquid component of a silica gel with air. They are generally synthesized via a sol-gel process in a liquid medium and then dried, usually by extraction with a supercritical fluid, the one most commonly used being supercritical C0 2. This type of drying makes it possible to avoid shrinkage of the pores and of the material.
  • the sol-gel process and the various drying operations are described in detail in Brinker C.J., and Scherer G.W., Sol-Gel Science: New York: Academic Press, 1990.
  • Hydrophobic silica aerogel particles which may be used in the present invention can have a specific surface area per unit of mass (S M ) ranging from 500 to 1500 m 2 /g, preferably from 600 to 1200 m 2 /g and better still from 600 to 800 m 2 /g, and a size expressed as the volume-average diameter (D[0.5]) ranging from 1 to 1500 pm, better still from 1 to 1000 pm, preferably from 1 to 100 pm, in particular from 1 to 30 pm, more preferably from 5 to 25 pm, better still from 5 to 20 pm and even better still from 5 to 15 pm.
  • S M specific surface area per unit of mass
  • D[0.5] volume-average diameter
  • the hydrophobic silica aerogel particles which may be used in the present invention have a size, expressed as volume-average diameter (D[0.5]), ranging from 1 to 30 mm, preferably from 5 to 25 mm, better still from 5 to 20 pm and even better still from 5 to 15 pm.
  • D[0.5] volume-average diameter
  • the specific surface area per unit of mass can be any substance having the specific surface area per unit of mass.
  • the BET specific surface area corresponds to the total specific surface area of the particles under consideration.
  • the sizes of the silica aerogel particles may be measured by static light scattering using a commercial particle size analyser such as the
  • hydrophobic silica aerogel particles which may be used in the present invention have a specific surface area per unit of mass (S M ) ranging from 600 to 800 m 2 /g and a size expressed as the volume-average diameter (D[0.5]) ranging from 5 to 20 pm and even better still from 5 to 15 pm.
  • S M specific surface area per unit of mass
  • D[0.5] volume-average diameter
  • the silica aerogel particles which may be used in the present invention may advantageously have a tapped density p ranging from 0.02 g/cm 3 to 0.10 g/cm 3 , preferably from 0.03 g/cm 3 to 0.08 g/cm 3 and preferably from 0.05 g/cm 3 to 0.08 g/cm 3 .
  • the hydrophobic silica aerogel particles which may be used in the present invention have a specific surface area per unit of volume S ranging from 5 to 60 m 2 /cm 3 , preferably from 10 to 50 m 2 /cm 3 and better still from 15 to 40 m 2 /cm 3 .
  • S v S M x p, where p is the tapped density, expressed in g/cm 3 , and S M is the specific surface area per unit of mass, expressed in m 2 /g, as defined above.
  • the hydrophobic silica aerogel particles which may be used according to the invention have an oil-absorbing capacity, measured at the wet point, ranging from 5 to 18 ml/g, preferably from 6 to 15 ml/g and better still from 8 to 12 ml/g.
  • the absorbing capacity measured at the wet point, noted Wp corresponds to the amount of oil that needs to be added to 100 g of particles in order to obtain a homogeneous paste. It is measured according to the "wet point" method or the method for determining the oil uptake of a powder described in standard NF T 30-022.
  • the aerogels which may be used according to the present invention are hydrophobic silica aerogels, preferably of silyl silica (INCI name: silica silylate).
  • hydrophobic silica is understood to mean any silica of which the surface is treated with silylating agents, for example with halogenated silanes, such as alkylchlorosilanes, siloxanes, in particular dimethylsiloxanes, such as
  • hexamethyldisiloxane or silazanes, so as to functionalize the OH groups with silyl Si-Rn groups, for example trimethylsilyl groups.
  • compositions of the present invention contain less than 1 % surfactant.
  • compositions of the present invention contain less than 0.5% surfactant.
  • compositions of the present invention when the compositions are in the form of a gel composition, the compositions of the present invention contain no surfactant.
  • compositions are in the form of an emulsion
  • surfactants or emulsifiers which may be used in compositions of the present invention
  • low HLB emulsifier(s) HLB value less than 8
  • intermediate HLB emulsifier(s) HLB value of 8 to 16
  • high HLB emulsifier(s) HLB value greater than 16
  • HLB refers to the“hydrophilic-lipophilic balance” associated with emulsifiers.
  • “HLB” value relates to the ratio of hydrophilic groups and lipophilic groups in emulsifiers, and also relates to solubility of the emulsifiers.
  • Lower HLB emulsifiers are more soluble in oils (lipophilic material) and are more appropriate for use in water-in-oil (W/O) emulsions.
  • W/O water-in-oil
  • Higher HLB emulsifiers are more soluble in water (hydrophilic material) and are more appropriate for oil-in-water (O/W) emulsions.
  • Particularly preferred emulsifiers in emulsion compositions of the present invention include alkoxylated silicone emulsifiers, such as pegylated silicone emulsifiers such as, for example, PEG dimethicone emulsifiers, where the amount of PEG (polyethylene glycol) groups on the dimethicone preferably ranges from 1 to 100, preferably from 2 to 50, preferably from 3 to 25, including all ranges and subranges therebetween.
  • alkoxylated silicone emulsifiers such as pegylated silicone emulsifiers such as, for example, PEG dimethicone emulsifiers, where the amount of PEG (polyethylene glycol) groups on the dimethicone preferably ranges from 1 to 100, preferably from 2 to 50, preferably from 3 to 25, including all ranges and subranges therebetween.
  • the composition is an emulsion composition in the form of a primer composition
  • a high HLB emulsifier and an low HLB emulsifier are present in a weight ratio of 10: 1 to 1 : 10, preferably a weight ratio of 5: 1 to 1 :5, preferably a weight ratio of 3:1 to 1 :3, including all ranges and subranges therebetween such as, for example, 7.5:1 to 1.5:1 , 6:1 to 3:1 , 1.5:1 to 1 :5, 3:1 to 1 :2, etc.
  • high and low HLB emulsifiers are present in such ratios in a primer composition, improved anti-pilling properties result when colored cosmetic compositions are applied to such primer compositions.
  • compositions of the present invention to the keratinous material in an amount sufficient to treat, care for and/or make up the keratinous material.
  • “making up” the keratinous material includes applying at least one coloring agent to the keratinous material in an amount sufficient to provide color to the keratinous material.
  • compositions of the present invention are provided.
  • the compositions of the present invention are applied topically to the desired area of the keratinous material in an amount sufficient to treat, care for and/or make up the keratinous material, to cover or hide defects associated with keratinous material, or to enhance the appearance of keratinous material.
  • the compositions may be applied to the desired area as needed, preferably once daily, and then preferably allowed to dry before subjecting to contact such as with clothing or other objects.
  • the composition is allowed to dry for about 4 minutes or less, more preferably for about 2 minutes or less.
  • Particularly preferred embodiments of the present invention include: [00193] 1. A composition comprising at least one copolymer of vinylpyrrolidone and acrylic acid and at least one film forming agent;
  • a gel composition comprising water, at least one copolymer of vinylpyrrolidone and acrylic acid, at least one coloring agent, and at least one film forming agent selected from the group consisting of (1 ) polymers including imide group(s), (2) low molecular weight sulfopolyester compounds, and (3) mixtures thereof, wherein the copolymer of vinylpyrrolidone and acrylic acid and the film forming agent are present in an active solid content weight ratio of greater than or equal to 1 :1 ;
  • composition of embodiment 2, wherein the coloring agent is a pearlescent pigment
  • composition of embodiments 2-3, wherein the at least one film forming agent is a polymer including imide group(s), in particular polyimide-
  • composition of embodiments 2-3, wherein the at least one film forming agent is is a low molecular weight sulfopolyester compound
  • composition is a gel composition comprising water, at least one crosslinked, linear copolymer of vinylpyrrolidone and acrylic acid, at least one pigment, and at least one film forming agent selected from the group consisting of (1 ) polymers including imide group(s), (2) low molecular weight sulfopolyester compounds, and (3) mixtures thereof, wherein the weight amount of copolymer of vinylpyrrolidone and acrylic acid present in the compositions of the present invention is greater than the weight amount of film forming agent; [00199] 7.
  • the pigment is a pearlescent pigment
  • An oil-in-water emulsion composition comprising water, at least one polymer including imide group(s), in particular polyimide-1 , at least 10% by weight of the weight of the composition of at least one humectant, and at least one copolymer of vinylpyrrolidone and acrylic acid;
  • composition of embodiment 9, wherein the composition is free of coloring agent
  • composition of embodiments 9-10 in the form of a primer composition
  • composition of embodiments 9-11 further comprising at least one low HLB emulsifier and at least one high HLB emulsifier, in particular PEG dimethicone emulsifier;
  • composition in example 1 was used as a base composition, and various amounts of film forming agent were added to this base composition to produce different compositions (as reflected in the Tables below).
  • compositions were tested for oil-resistance and adhesion using the following protocols:
  • Oil-Resistance Protocol Use a 3m I drawdown bar to drawdown the composition on abrasion paper. Let it dry for 24 hours. After drying, put a drop of artificial sebum on top of it, wait for 5 minutes and use kimwipe to wipe it back and forth 5 time and evaluate the amount of composition transferred on the kimwipe as well as the residual of the drawdown on the paper.
  • Adhesion Protocol Press a piece of pressure-sensitive tape on the drawdown film and quickly remove the tape. The adhesion was rated by the amount of the composition be removed by the tape. The tape used in the adhesion test is ASTM D3359 cross hatch adhesion test tape.
  • Example 4 Examples Determining Surface Energy Of
  • Example 5 Examples Determining Playtime Improvement

Abstract

L'invention concerne des compositions comprenant au moins un copolymère de vinylpyrrolidone et d'acide acrylique et au moins un agent filmogène, et des procédés d'application de telles compositions sur des matières kératiniques.
PCT/US2020/044146 2019-07-31 2020-07-30 Compositions contenant un copolymère de vinylpyrrolidone et d'acide acrylique et agent de formation de film WO2021021978A1 (fr)

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US16/527,675 US11878067B2 (en) 2019-07-31 2019-07-31 Gel compositions containing copolymer of vinylpyrrolidone and acrylic acid
US16/527,632 US20210030636A1 (en) 2019-07-31 2019-07-31 Emulsion compositions containing polymer including imide group(s), humectant, and copolymer of vinylpyrrolidone and acrylic acid
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