WO2014011456A9 - Compositions comprenant des particules solides encapsulées dans une matrice de silicone réticulée, et procédés de fabrication de celles-ci - Google Patents

Compositions comprenant des particules solides encapsulées dans une matrice de silicone réticulée, et procédés de fabrication de celles-ci Download PDF

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Publication number
WO2014011456A9
WO2014011456A9 PCT/US2013/049161 US2013049161W WO2014011456A9 WO 2014011456 A9 WO2014011456 A9 WO 2014011456A9 US 2013049161 W US2013049161 W US 2013049161W WO 2014011456 A9 WO2014011456 A9 WO 2014011456A9
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Prior art keywords
cross
particles
composition
silicone
treated
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PCT/US2013/049161
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English (en)
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WO2014011456A1 (fr
Inventor
Wilson A. LEE (Dr.)
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Elc Management Llc
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Priority claimed from US13/544,297 external-priority patent/US8932639B2/en
Application filed by Elc Management Llc filed Critical Elc Management Llc
Priority to JP2015521658A priority Critical patent/JP2015522071A/ja
Priority to KR20157000194A priority patent/KR20150018868A/ko
Priority to AU2013288950A priority patent/AU2013288950A1/en
Priority to EP13817152.5A priority patent/EP2869812A4/fr
Priority to CA2877317A priority patent/CA2877317A1/fr
Priority to CN201380036884.XA priority patent/CN104640535A/zh
Publication of WO2014011456A1 publication Critical patent/WO2014011456A1/fr
Publication of WO2014011456A9 publication Critical patent/WO2014011456A9/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/27—Zinc; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/29—Titanium; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—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
    • A61K8/8141—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8164—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 carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers, e.g. poly (methyl vinyl ether-co-maleic anhydride)
    • 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
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/893—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone
    • 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
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/60—Particulates further characterized by their structure or composition
    • A61K2800/61—Surface treated
    • A61K2800/62—Coated
    • A61K2800/622—Coated by organic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/60—Particulates further characterized by their structure or composition
    • A61K2800/61—Surface treated
    • A61K2800/62—Coated
    • A61K2800/623—Coating mediated by organosilicone compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/60—Particulates further characterized by their structure or composition
    • A61K2800/65—Characterized by the composition of the particulate/core
    • A61K2800/651—The particulate/core comprising inorganic material

Definitions

  • the present invention relates to topical compositions comprising stabilized particulate components, as well as methods of making the same.
  • Cosmetic or topical compositions typically comprise one or more particulate components, such as, for example, pigments or dyes, fillers, thickeners, sunscreen agents, and the like. Such particulate components are often insoluble in the respective solvent or carrier system and remain dispersed or suspended in the cosmetic or topical compositions.
  • particulate components such as, for example, pigments or dyes, fillers, thickeners, sunscreen agents, and the like.
  • the dispersed or suspended particles may agglomerate with one another and precipitate out of the composition.
  • the smaller the particle size, the larger the active surface area, and the more susceptible such particulate components are toward adverse interactions or interference with other ingredients or components in the cosmetic or topical compositions, which may destabilize the cosmetic or topical compositions or reduce the overall performance thereof.
  • particulate components that are less than 40nm in size can penetrate into the skin and lead to apoptosis.
  • the present invention relates to a topical composition
  • a topical composition comprising a dispersion of treated particles in a cosmetically or pharmaceutically acceptable carrier, wherein each of the treated particles comprises one or more core particles encapsulated in a cross-linked silicone matrix, and wherein each of the treated particles possesses an electrical potential in the range of from about -40mV to about -80mV.
  • the present invention relates to a treated particle comprising one or more titanium dioxide or zinc oxide core particles encapsulated in a cross-linked silicone matrix, while the treated particle has a particle size ranging from about 1 micron to about 50 microns and possesses an electrical potential in the range of from about -40mV to about - 80mV.
  • the present invention relates to a method for forming treated particles, comprising:
  • cross-linking agent comprises a stannous carboxylate capable of effectuating cross-linking of the silicone coating, thereby forming a cross-linked structure with the core particles encapsulated therein;
  • the lone figure is a microscope image of a treated particle formed by first coating Ti0 2 core particles with silicone, then cross-linking the silicone coating to form a cross-linked structure, followed by milling/grinding of the cross-linked structure, according to one embodiment of the present invention.
  • the present invention provides stabilized particulate components that are useful in cosmetic or topical compositions, as well as methods for stabilizing particulate components.
  • the treated particles which are formed by encapsulating the particulate components in a cross-linked silicone matrix, are characterized by an average particle size that is at least 10 times, preferably 20 times, more preferably 50 times, and most preferably 100 times, larger than the average particle size of the initial particulate components.
  • Each of the treated particles comprises a cross-linked silicone matrix encapsulating therein one or more core particles.
  • the physical and/or chemical properties of the entrapped core particles pertaining to or associated with their desired activities in the cosmetic or topical compositions are not adversely affected, while the significantly larger treated particles provide improved structural and spatial stability.
  • the core particles useful for the present invention can be any particulate components that are commonly used in cosmetic or pharmaceutical compositions, which include, but are not limited to: mineral pigments and fillers such as, for example, talc, kaolin, mica, bismuth oxychloride, chromium hydroxide, barium sulfate, polymethylmethacrylates (PMMA), boron nitride, nylon beads, polymeric powders (e.g., BPD 500 powders comprised of hexamethylene diisocyanate/trimethylol hexyllactone crosspolymer and silica that is commercially available from Kobo Products, Inc.
  • mineral pigments and fillers such as, for example, talc, kaolin, mica, bismuth oxychloride, chromium hydroxide, barium sulfate, polymethylmethacrylates (PMMA), boron nitride, nylon beads, polymeric powders (e.g., BPD 500 powders comprised of
  • the core particles are comprised of a material capable of generating free oxygen radicals, and more preferably a metal oxide such as zinc oxide or titanium dioxide.
  • the core particles can be of any regular or irregular shape, such as, for example, spherical, cubic, cylindrical, planar, fibrous, laminar, and the like.
  • the average particle size of the core particles as used in the present invention is preferably less than 1 micron, more preferably from about 0.001 micron to about 0.5 micron, and most preferably from about 0.01 to about 0.05 micron.
  • a particularly preferred example of the core particles is a manganese modified titanium dioxide particle commercially available under the trade name of OptisolTM from Croda, Inc. at Edison, NJ.
  • the core particle preferably constitutes about 10 to about 99 percent by weight of the treated particle, and more preferably, about 40 to 90 percent by weight of the treated particle.
  • Encapsulation of the core particles can be readily achieved in the present invention by first coating the core particles with silicone, then contacting the coated particles with a cross- linking agent comprising a stannous carboxylate capable of effectuating cross-linking of the silicone coating so as to form a cross-linked structure with the core particles encapsulated therein, and followed by reducing the cross-linked structure into treated particles of desired size.
  • a cross- linking agent comprising a stannous carboxylate capable of effectuating cross-linking of the silicone coating so as to form a cross-linked structure with the core particles encapsulated therein, and followed by reducing the cross-linked structure into treated particles of desired size.
  • the silicone as used in the present invention is preferably a silicone with branched reactive moieties.
  • branched reactive moieties refers to side chain moieties that are branching off the polymeric backbone of the hydrophobic polymer and are capable of forming chemical bonds (which include, but are not limited to: van der Waals' bonds, hydrogen bonds, covalent bonds, and ionic bonds) with the surface of the core particle.
  • the branched reactive moieties of the hydrophobic polymer of the present invention may include, but are not limited to: amino moieties, imino moieties, halogen moieties, hydroxyl moieties, and alkoxyl moieties.
  • the polyorganosiloxane backbone of the silicone forms a continuous coating over the core particles, while the branched reactive moieties of the silicone extend inwardly to the surface of the core particle and form a chemical bond with the core particle, thereby welding or anchoring the entire silicone coating onto the core particle.
  • the silicone is a reactive ethoxy modified silicone with ethoxy or ethoxysilylethyl branched moieties, as described in U.S. Patent 6,660,281, the content of which is incorporated herein by reference in its entirety for all purposes.
  • Suitable reactive ethoxy modified silicones are commercially available under the trade names KF9901, KF9908, KF9909 or KP574 from Shin-Etsu Silicones of America, Inc., Akron, OH.
  • the hydrophobic polymer of the present invention comprises a triethoxysilylethyl polydimethylsiloxyethyl hexyl dimethicone, which is commercially available under the trade name KF9909 from Shin-Etsu.
  • the silicone is preferably present in an amount of about 0.01 to about 50 percent by total weight of the treated particle, and preferably, about 0.5 to about 15.0 percent by total weight of the treated particle.
  • the silicone as described hereinabove can be coated onto the core particles using any known coating technique, such as simple mixing, spray drying, fluid bed coating, and the like.
  • the silicone is coated onto the core particles using techniques involving localized heat treatment, such as, for example, sonication achieved by using an Ultrasonic Processor, model # UPP-400A, Cycles: 20 KHz, available from Sonicor Instrument Corp., Copiague, NY.
  • the core particles are provided in batches of from about 100 grams to about 1 kilogram, and each batch is mixed with a solution or dispersion of silicone.
  • the mixture is then sonicated to form a silicone coating over the core particles in a period of time ranging from about 15 minutes to about 2 hours, and preferably from 10 minutes to about 1 hour.
  • the branched reactive alkoxyl moieties of the silicone are energized and consequently form chemical bonds with the surface of the core particles, thereby cladding the polyorganosiloxane backbone of the silicone onto the surface of the core particles and forming a securely attached silicone coating thereover.
  • the silicone-coated particles are subjected to a centrifugation step whereby any residual silicone is removed from the batch of silicone-coated particles.
  • the silicone- coated particles are dried by placing them in an oven for about 12 to 19 hours at a temperature at least sufficient to remove any residual water by evaporation (for example, about 100°C to about 120°C).
  • a cross- linking agent which is preferably a stannous carboxylate capable of effectuating cross-linking of the silicone coating.
  • Suitable stannous carboxylates that can be used as the cross-linking agent of the present invention include, but are not limited to stannous salts of linear or branched Cs-Ci2 alkyl carboxylic acids, among which stannous octoate is the most preferred.
  • stannous octoate demonstrates in the present invention the capability of effectively cross-linking the silicone as described hereinabove at room temperature (i.e., 25°C) upon continuous mixing for a period of time ranging from about 30 seconds to about 5 minutes, more preferably from about 45 seconds to about 2 minutes, and most preferably for about 1 minute.
  • the mixture is then allowed to sit for from about 1 minute to about 45 minutes, and a cross-linked structure is thereby formed with the core particles encapsulated therein.
  • the cross-linked structure readily conforms to the shape of the container in which it is allowed to form. For example, if the mixture is poured onto a flat surface, the cross-linked structure will be formed into a flat sheet. For another example, if the mixture is poured into a cubic container, the cross-linked structure will be formed into a cube.
  • the cross-linked structure so formed is typically a relatively solid structure.
  • Such cross-linked structure can be subsequently reduced into treated particles of desired average particle size by any suitable methods, such as crushing, grinding, pulverizing, milling, filtering, and the like.
  • the resulting treated particles preferably have an average particle size ranging from about 1 micron to about 50 microns, more preferably from about 1 to about 15 microns, and most preferably from about 5 to about 8 microns, as determined by a Malvern Particle Size Analyzer, available from Malvern Instrument at Worcestershire, UK.
  • the entrapped core particles may account for from about 10% to about 90% of the total weight of the resulting treated particles, more preferably 30%> to about 75% of the total weight, and most preferably from about 40% to about 60% of the total weight.
  • the cross-linked silicone may account for from about 5% to about 75% of the total weight of the resulting treated particles, more preferably from about 10% to about 60% of the total weight, and most preferably from about 30% to about 50% of the total weight.
  • the figure shows a microscopic view of a treated particle formed by the process described hereinabove, according to one embodiment of the present invention.
  • submicron particles particularly those that are less than 40nm in size, can penetrate or be engulfed into the skin cells and consequently lead to apoptosis.
  • the inventor has discovered that one of the ways to prevent particles from penetrating into the cells is to modify the particles to have the same charge as the skin cells. Human skin and blood cells are known to be negatively charged, the skin cells possessing a negative charge of about -24mV.
  • the inventor has also found that when the particles possess an electrical potential which is at least 2.5 to 3 times the electrical potential of skin cells, a repulsive force between the particles and the skin is created. As a result, penetration of the particles into the cells can be prevented.
  • the core particles are first coated with an inner layer of an anionic polymer before being encapsulated into the cross-linked silicone matrix.
  • the core particles are first coated with the anionic polymer and then with silicone followed by sonication, thereby forming coated particles that each comprises an inner coating of the anionic polymer and an outer coating of the silicone.
  • Such coated particles are subsequently treated by cross-linking the outer silicone coating in the presence of a cross-linking agent as described hereinabove to form the cross-linked structure with the core particles encapsulated therein.
  • the anionic polymer is believed to impart a negative charge to the overall treated particle.
  • any anionic polymer possessing an electrical potential ranging from about -lOmV to -100 mV, more preferably from about -30mV to - 80mV, which will impart to the treated particle an electrical potential ranging from about - 40mV to -80mV, more preferably from about -50mV to -70mV, can be used. It is important to select a polymer with a suitable electrical potential, because if the electrical potential of the treated particle is too low, the repulsion between the skin and the treated particles would be insufficient to prevent the particles from penetrating into the skin. On the other hand, if the electrical potential of the treated particles is too high, then the particles would not disperse properly when used in a composition.
  • the electrical potential can be measured by diluting 0.1 part of the specimen in 30 parts of 99% ethanol and using a Zeta potential analyzer, such as the Zetasizer Nano available from Malvern Instruments Ltd, Worcestershire, UK.
  • the Zeta potential is a measure of the magnitude of charge repulsion or attraction between particles.
  • the particles of the present invention possessing an electrical potential ranging from about -40mV to - 80mV, such as those containing an inner layer of an anionic polymer, will not settle into the wrinkles or creases on the skin surface when situated on the surface of the skin due to the repulsive forces between the skin and the treated particles.
  • coating the surface of the particles (e.g. titanium dioxide) with 2% PVM/MA by total weight of the treated particles generates approximately -64mV in a solvent system of water and/or alcohol.
  • the two like charges of the skin cells and the particles repel one another, and this repulsive force can be measured.
  • the negative charge is trapped within the inner layer between the core particle and the outer cross-linked silicone matrix, and thereby becoming localized or immobilized around the core particle. As a result, a uniform negative charge is created around the entire particle.
  • the branched reactive alkoxyl moieties of the silicone in the outer matrix are believed to extend through the inner layer of the anionic polymer onto the surface of the core particle, preferably forming chemical bonds therewith to anchor the silicone layer as well as entrap the inner layer onto the core particle surface.
  • the anionic polymer preferably has a higher density than the silicone but a lower density than the core particle.
  • the anionic polymer and the silicone can be sequentially coated onto the surface of the core particle, and the anionic polymer can be successfully entrapped between the core particle surface and the outer silicone layer. More preferably, a density difference of at least 0.01 g/cm 3 exists between the anionic polymer and the silicone so as to ensure the desired sequential deposition thereof.
  • anionic polymers examples include, but are not limited to, anionic copolymers such as acrylates copolymers and methyl vinyl ether and maleic anhydride (PVM/MA) copolymers.
  • anionic copolymers such as acrylates copolymers and methyl vinyl ether and maleic anhydride (PVM/MA) copolymers.
  • Acrylates copolymers include, but are not limited to, the Aculyn series of copolymers available from The Dow Chemical Company, Philadelphia, PA.
  • the anionic polymer is a
  • the Gantrez copolymers include, for example, Gantrez AN-119, Gantrez AN-139, Gantrez AN-149, Gantrez AN-169, Gantrez AN-903, and Gantrez S-97BF.
  • the Gantrez copolymers are white, free-flowing powders that are initially insoluble in water, but they can be easily dispersed in water where the polymeric anhydride gradually hydrolyzes to produce a transparent solution of the free acid.
  • the Gantrez copolymers contain methyl vinyl ether and maleic anhydride moieties but are differentiated from one another by molecular weights, which range widely from about 200,000 (for Gantrez AN-119) to about 2,000,000 (for Gantrez AN-179). More preferably, the anionic polymer used for forming the inner layer in the present invention comprises Gantrez AN-149 or Gantrez S-97BF.
  • the inner layer may be present in an amount of about 0.2 to 5.0 percent by weight of the treated particle, and preferably, 0.5 to 2.0 percent by weight of the treated particle.
  • an active agent can be co-encapsulated with the core particles into the cross-linked silicone matrix, either with or without the inner layer of anionic polymer.
  • the active agent is preferably a hydrophilic active agent including, but not limited to: water-soluble preservatives,
  • water-soluble extracts include but are not limited to, extracts from, artemia, phytosphingosine, polygonum cuspidatum root, yeast such as saccharomyces lysate, thermos thermophillus ferment, birch (Betula alba), mimosa tenuiflora (bark) extract, fruit, clove, rye, malt, corn, spelt, millet, barley, oat, wheat, sesame, cumin, turmeric, green onion, celery, ginseng, ginger, licorice, carrot, bupleurum root, Ginkgo biloba (gingko), Foeniculi Fructus (fennel), kiwi, berry such as Morus bombycis (mulberry),
  • Gentiana lutea (gentian), algae such as red algae, Arctium lappa (burdock), Salvia officinalis (sage), Lentinus edodes (shiitake mushroom), Perilla frutescens (perilla), Filipendula
  • Multijuga, Fucus vesiculosis (bladderwrack, sea weed), peach kernel, Allium sativum (garlic), Poria cocos (poria), Humulus lupulus (hops), Mutan Cortex (Moutan Bark), Pimpinella major, Lactuca sative (lettuce), Astragalus membranaceous (astragalus) and Rosmarinus officinalis (rosemary), Prunus amygdalus (almond), Althea officinale (althea), aloe, Rosae Fructus (rose fruit, or Rosa multiflora), Scuttelaria baicalensis (Huang qin), Puerariae Radix (Pueraria Root, or Pueraria lobata), chamomile such as Chamomillae Flos (German chamomile), Gardenia jasminoides (zhii zi, Gardeniae Fructus), Sophora flavescens A
  • Pericarpium bitster orange peel
  • Ruscus aculeatus butcher's bloom
  • Vitis vinifera grape
  • Tilia japonica lime
  • Citrus junos and Rosa canina rose hip
  • caffeine Cinnamomi Cortex (cinnamon bark) and Eriobotrya japonica Lindl. (loquat)
  • Gambir Echinacea
  • Phellodendri Cortex amur cork tree or Phellodendron amurense
  • Hypericum perforatum St.
  • Calendula officinalis pot marigold
  • Houttuynia cordata Houttuyniae Herba, Houttuynia Herba
  • Potentilla erecta Petroselinum crispum (parsley), Parietaria officinalis, Santalum album (sandalwood), Prunus persica (peach), Centaurea cyanus (cornflower), Eucalyptus globulus (eucalyptus) and Lavandula angustifolia (lavender), Persea americana (avocado), Nasturtium officinalis (watercress), Symphytum officinale (comfrey), Asarum sieboldii (wild ginger), Xanthoxyum piperitum (Japan pepper), Rehmannia glutinosa (di huang), Mentha piperita (peppermint), Syzygium aromaticum (clove), Tussilago farfara
  • the active agent preferably, is an antioxidant or a natural water-soluble extract having antioxidant activities. More preferably, the active agent is a grape seed extract or a French maritime pine tree bark extract (also referred to as pycnogenol).
  • the hydrophilic active agent can be present in the treated particle of the present invention in an amount of about 0.01 to 50.0 percent, and preferably, about 0.25 to 30.0 percent by weight of the treated particle.
  • the treated particles, according to one preferred embodiment, of the present invention as illustrated hereinabove can be readily formed, for example, by adding an anionic polymer and optionally a hydrophilic active agent, such as an antioxidant, into a specific solvent system to solubilize the anionic polymer and the hydrophilic active agent.
  • a specific solvent system for practicing the present invention may contain a single solvent or a mixture of two or more solvents. Suitable solvents that can be used for forming such a solvent system include, but are not limited to: water, alcohols, and organic solvents, such as ethers, ketones, aliphatic hydrocarbons, halogenated hydrocarbons, and the like.
  • the solvent system as used in the present invention is an aqueous solvent system containing water and optionally one or more alcohols.
  • Core particles to be treated can then be added into the aqueous solution of anionic polymer and hydrophilic active agent and mixed until uniform.
  • a silicone with branched reactive alkoxyl moieties is added into the aqueous solution, preferably with additional water and alcohol.
  • the mixture is then sonicated for a sufficient period of time so as to form coated particles having an inner layer of anionic polymer and an optional hydrophilic active agent and an outer layer of hydrophobic polymer that are securely attached to the core particle, i.e., with little or no flaking-off.
  • a cross-linking agent e.g., stannous octoate
  • a cross-linking agent e.g., stannous octoate
  • the resulting mixture is next poured into a container and allowed to sit for a sufficient period time to thereby forming a cross-linked structure, which is subsequently reduced to treated particles of desirable particle size by grinding, milling, crushing, pulverizing, filtering, and the like.
  • the treated particles of the present invention provide various advantages and benefits that are not available in their un- encapsulated or "naked” counterparts.
  • the core particles encapsulated in the cross-linked silicone matrix are sealed off from potentially destabilizing or degrading active ingredients in the topical composition, they are significantly more stable than their un- encapsulated or "naked” counterparts.
  • the core particles contain material or materials potentially capable of causing generation of reactive oxygen species (ROS), which may in turn degrade or otherwise interfere with other active ingredients in the topical composition
  • ROS reactive oxygen species
  • Encapsulation by the cross-linked silicone matrix may also alter the hydrophobicity/hydrophilicity of certain core particles that are intrinsically hydrophilic and allow such core particles to be formulated into oil or silicone phases that are typically incompatible with the un-encapsulated or "naked” hydrophilic particles. It is important to note that the desired chemical and/or physical properties of the core particles should remain substantially unaffected by the encapsulation described hereinabove.
  • ROS reactive oxygen species
  • ROS if not reduced or eliminated timely, may cause extensive damage to all components of living cells, including proteins, lipids, and DNA.
  • Various enzymes produced by the living cells such as superoxide dismutase, catalase, and glutathione peroxidase, function as cellular antioxidants to eliminate the excess reactive oxygen species. Consequently, the ROS are present only at low levels in normal living cells, and the damage caused by them is constantly repaired by various cellular repair mechanisms.
  • the ROS levels can increase dramatically, which may lead to an imbalance between the production of ROS by a biological system and the biological system's capability to detoxify the reactive
  • Oxidative stress is involved in many diseases, such as atherosclerosis, Parkinson's disease and Alzheimer's disease. Oxidative stress is also believed to be a major contributor to the aging process. Certain particles commonly used in cosmetic compositions, such as iron oxides, titanium dioxide, and zinc oxide, are known to cause generation of ROS, which not only can exert oxidative stress on the skin, but may also interfere with other ingredients or components in the cosmetic compositions. For example, many organic dyes/colorants, organic sunscreen agents, and other organic cosmetic ingredients are known to be susceptible to oxidative decomposition or degradation.
  • ROS-releasing particles may consequently lead to in situ decomposition or degradation of such organic cosmetic ingredients and adversely affect the overall performance and stability of the cosmetic compositions.
  • Encapsulation of such ROS-releasing particles into the cross-linked silicone matrix of the present invention is believed to effectively eliminate or reduce any potential oxidative stress that such particles may exert on the skin, and to prevent such particles from causing the decomposition or degradation of other cosmetic ingredients. Consequently, the cross-linked silicone- encapsulated metal oxide particles of the present invention can be readily used with organic compounds that are known to be susceptible to oxidative decomposition or degradation to form topical or cosmetic compositions with significantly improved overall stability and prolonged shelf life.
  • the treated particles of the present invention can be added directly to any one of the following ingredients of the present invention.
  • pharmaceutically or cosmetically acceptable carrier to form a cosmetic or topical composition.
  • pharmaceutically or cosmetically acceptable carriers are substances that are biologically compatible with human skin and can be used to formulate active ingredients described hereinabove and/or hereinafter into a cream, gel, emulsion, liquid, suspension, powder, nail coating, skin oil, or lotion that can be topically applied.
  • the cosmetically acceptable carrier is in the form of an emulsion, it may contain from about 0.1 to 99%, preferably from about 0.5 to 95%, more preferably from about 1 to 80% by weight of the total composition of water and from about 0.1 to 99%, preferably from about 0.1 to 80%, more preferably from about 0.5 to 75% by weight of the total composition of oil.
  • the composition may comprise from about 0.1 to 90 wt% of oil and from about 0.1 to 75 wt% of other ingredients such as pigments, powders, non-aqueous solvents (such as mono-, di-, or polyhydric alcohols, etc.
  • the composition in the form of an aqueous based gel, solution, or suspension, it may comprise from about 0.1 to 99 wt% of water and from about 0.1 to 75 wt% of other ingredients such as botanicals, nonaqueous solvents, etc.
  • the pharmaceutically or cosmetically acceptable carrier or carriers can be present in the topical or cosmetic composition of the present invention at an amount ranging from about 0.1%) to about 99.9%), preferably from about 5% to about 99.5%, more preferably from about 10% to about 99%, and most preferably from about 10% to 90% by total weight of the topical or cosmetic composition.
  • the topical or cosmetic composition may contain one or more skin care actives, which are agents that provide benefits to the skin, rather than merely improving the physical or aesthetic characteristics of the topical composition. If present, such skin care actives may range from about 0.01 to 50%, preferably from about 0.05 to 35% by weight of the total composition.
  • Exemplary skin care additives that can be used in the topical or cosmetic compositions of the present invention include, but are not limited to: chemical or physical sunscreens, self-tanning agents such as dihydroxyacetone, anti-acne agents (e.g., resorcinol, salicylic acid, benzoyl peroxide, and the like), enzyme-inhibiting agents, collagen-stimulating agents, agents for the eradication of age spots and keratoses, analgesics, anesthetics, antimicrobials (e.g., antibacterials, antiyeast agents, antifungal agents, and antiviral agents), antidandruff agents, antidermatitis agents, antipruritic agents, antiemetics, anti-inflammatory agents, antihyperkeratolytic agents, antiperspirants, antipsoriatic agents, antiseborrheic agents, antihistamine agents, skin lightening agents, depigmenting agents, skin soothing/healing agents (e.g., aloe vera extract
  • the topical composition comprises one or more skin care actives selected from the group consisting of sunscreen agents, self-tanning agents, anti-aging agents, anti-wrinkle agents, anti-acne agents, antimicrobials, anti-inflammatory agents, skin-lightening agents, proteins or peptides, vitamins and derivatives thereof, exfoliants, ingredients that stimulate DNA repair, ingredients that provide immune protection, ingredients that stimulate cell renewal, ingredients that stimulate skin barrier repair, moisturizers, and mixtures thereof.
  • sunscreen agents selected from the group consisting of sunscreen agents, self-tanning agents, anti-aging agents, anti-wrinkle agents, anti-acne agents, antimicrobials, anti-inflammatory agents, skin-lightening agents, proteins or peptides, vitamins and derivatives thereof, exfoliants, ingredients that stimulate DNA repair, ingredients that provide immune protection, ingredients that stimulate cell renewal, ingredients that stimulate skin barrier repair, moisturizers, and mixtures thereof.
  • the topical or cosmetic composition is a sunscreen composition comprising treated particles containing core particles formed of zinc oxide, titanium dioxide, or both.
  • zinc oxide or titanium dioxide particles are known to have photoprotective characteristics and can therefore be used as physical sunscreen agents, but their uses in topical or cosmetic compositions are limited due to their photo-activity, i.e., their tendency to cause generation of reactive oxygen species upon exposure to UV light, which may degrade or otherwise interfere with certain organic cosmetic ingredients or skin care actives that are susceptible to oxidative
  • the treated particles of the present invention containing zinc oxide and/or titanium dioxide can be readily formulated with organic cosmetic ingredients or skin care additives that are known to be susceptible to oxidative decomposition or degradation to form stable sunscreen compositions with significantly improved overall stability and prolonged shelf live.
  • the treated particles containing zinc oxide and/or titanium dioxide can be formulated with one or more organic dyes susceptible to oxidative
  • the treated particles containing zinc oxide and/or titanium dioxide can be formulated with one or more organic sunscreen agents susceptible to oxidative decomposition or degradation, thereby forming sunscreen compositions that are not only characterized by high SPF values (e.g., SPF 30 or more), but also surprisingly and unexpectedly improved overall stability and prolonged shelf life. If present, such organic sunscreen agents may range from about 0.1 to 45% by weight of the total composition.
  • benzophenone-3 dioxybenzone, sulisobenzone, octabenzone, hydroxy- and/or methoxy- substituted benzophenones, and benzophenonesulfonic acids and salts thereof); salicylic acid derivatives (e.g., ethylene glycol salicylate, triethanolamine salicylate, octyl salicylate, homomenthyl salicylate, and phenyl salicylate); urocanic acid and derivatives thereof (e.g., ethyl urocanate); p-aminobenzoic acid (PABA) and derivatives thereof (e.g.,
  • ethyl/isobutyl/glyceryl esters thereof and 2-ethylhexyl p-dimethylaminobenzoate which is also referred to as octyldimethyl PABA
  • anthranilates and derivatives thereof e.g., o-amino- benzoates and various esters of amino-benzoic acid
  • benzalmalonate derivatives e.g., o-amino- benzoates and various esters of amino-benzoic acid
  • benzimidazole derivatives imidazolines; bis-benzazolyl derivatives; dibenzoylmethanes and derivatives thereof (e.g., 4-tert-butyl-4'-methoxydibenzoylmethane, which is commonly referred to as "avobenzone,” and 4-isopropyl-dibenzoylmethane); benzoazole/
  • benzodiazole/benzotriazoles and derivatives thereof e.g., 2-(2-hydroxy-5-methylphenyl) benzotriazole and methylene bis-benzotriazolyl tetramethylbutylphenol, which is commonly referred to as "Tinosorb M”
  • diphenylacrylates and derivatives thereof e.g., 2-ethylhexyl-2- cyano-3,3-diphenylacrylate, which is commonly referred to as “octocrylene,” and ethyl-2- cyano-3,3-diphenylacrylate, which is commonly referred to as “etocrylene”
  • diesters or polyesters containing diphenylmethylene or 9H-fluorene substitutional groups 2-phenyl- benzimidazole-5-sulphonic acid (PBSA); 4,4-diarylbutadienes; cinnamates and derivatives thereof (e.g., 2-ethylhexyl-p
  • naphthalates and derivatives thereof e.g., diethylhexyl-2,6-naphthalate
  • naphtholsulfonates and derivatives thereof e.g., sodium salts of 2-naphthol-3,6-disulfonic and 2-naphthol-6,8- disulfonic acids
  • dibenzalacetone and benzalacetonephenone diphenylbutadienes and derivatives thereof; di-hydroxynaphthoic acid and salts thereof; o- and p- hydroxybiphenyldisulfonates; coumarin derivatives ( e.g., 7-hydroxy, 7-methyl, and 3-phenyl derivatives thereof); azoles/diazoles/triazoles and derivatives thereof (e.g., 2-acetyl-3- bromoindazole, phenyl benzoxazole, methyl naphthoxazole, and various aryl benzotriazoles); quinine and derivative
  • hydroquinone and derivatives thereof hydroquinone and derivatives thereof; uric acid and derivatives thereof; vilouric acid and derivatives thereof, and mixtures or combinations thereof.
  • Salts and otherwise neutralized forms of certain acidic sunscreens from the list hereinabove are also useful herein. These organic sunscreen agents may be used alone or in combination of two or more. In addition, other known animal or vegetable extracts having UV light-absorbing ability may properly be used alone or in combination.
  • Organic sunscreen agents that are particularly useful for the practice of the present invention are: 4,4'-t-butyl methoxydibenzoylmethane, 2-ethylhexyl-2-cyano-3,3- diphenylacrylate, 2-ethylhexylsalicylate, 3,3,5-trimethylcyclohexylsalicylate, 2-ethylhexyl p- methoxycinnamate, 2-hydroxy-4-methoxybenzophenone, 2,2-dihydroxy-4- methoxybenzophenone, 2,4-bis- ⁇ 4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl ⁇ -6-(4- methoxyphenyl)-l,3,5-triazine, methylene bis-benzotriazolyl tetramethylbutylphenol, terephthalylidene dicamphor sulfonic acid, diethylhexyl 2,6-naphthalate, digallo
  • the sunscreen compositions of the present invention are provided in the sunscreen compositions of the present invention, either with Ti0 2 -containing treated particles, or ZnO-containing treated particles, or both. More preferably, the sunscreen compositions of the present invention further include a second organic sunscreen agent selected from the lists provided hereinabove.
  • the cosmetically acceptable carrier may also contain one or more oils, which may be silicone, organic, or mixtures thereof. If present, such oils may range from about 0.1 to 99% by weight of the total composition and include volatile or non- volatile silicones such as cyclomethicone; methyl trimethicone; octamethyltrisiloxane; decamethyltetrasiloxane;
  • dodecamethylpentasiloxane dimethicone; phenyl trimethicone trimethylsiloxyphenyl dimethicone; phenyl dimethicone; cetyl dimethicone; dimethicone copolyol, cetyl dimethicone copolyol; glycerolated silicones such as lauryl PEG-9 polydimethylsiloxyethyl dimethicone; or mixtures thereof.
  • Suitable esters include mono-, di-, or triesters of C4-30 fatty acids and mono- , di-, or polyhydric CI -20 alcohols, such as fatty acid (e.g., stearyl, behenyl, and isostearyl) esters of glycerin, or fatty acid esters of alpha hydroxyl acids such as citric, malic, or lactic acids and the like.
  • Suitable hydrocarbons include monomeric or polymeric olefins or alpha olefins, such as polyisobutene, polydecene, polybutene, or hydrogenated derivatives thereof.
  • the cosmetically acceptable carrier may also comprise one or more humectants. If present, they may range from about 0.1 to 20% by weight of the total composition and include CI -4 alkylene glycols such as butylene, propylene, ethylene glycol, glycerin and the like.
  • the cosmetically acceptable carrier may also contain one or more waxes preferably having a melting point ranging from about 30 to 150° C. If present, such waxes may range from about 0.1 to 45% by weight of the total composition and include animal, vegetable, mineral, or silicone waxes. Examples include alkyl dimethicones stearyl dimethicone, candelilla, polyethylene, ozokerite, beeswax, and the like.
  • the cosmetically acceptable carrier may also comprise one or more organosiloxane elastomers, either emulsifying or non-emulsifying. If present, such elastomers may range from about 0.1 to 30% by weight of the total composition. Examples of suitable elastomers include dimethicone/vinyl dimethicone crosspolymer; dimethicone/dimethicone PEG/PPG 10/15 crosspolymer; and the like.
  • the cosmetically acceptable carrier may also include one or more pigments or powders or mixtures thereof. If present, the suggested range of such pigments or powders is from about 0.1 to 85%o by weight of the total composition.
  • the particle sizes of such pigments or powders may range from about 0.05 to 200 microns but are preferably about 50-100 microns.
  • pigments examples include organic pigments such as D&C or FD&C colors or Lakes thereof including blues, browns, reds, etc; or inorganic iron oxides such as brown, yellow, green, red, iron oxides.
  • Suitable powders include titanium dioxide, nylon, PMMA, boron nitride, mica, and the like.
  • the cosmetically acceptable carrier may also comprise one or more nonionic surfactants, particularly if the topical or cosmetic composition of the present invention is provided in the emulsion form. If present, such surfactants may range from about 0.1 to 20% by weight of the total composition. Suitable surfactants include ethoxylated fatty C6-30 alcohols such as steareth, beheneth, ceteth where the number following each of the surfactants refers to the number of repeating ethylene oxide groups which may range from 2 to 250, e.g. steareth-2, beheth-30 and so on.
  • Ti0 2 particles were first coated with Gantrez S-97BF polymer and then with KF9909 silicone fluid under sonication, and the coated particles were then mixed with more KF9909 silicone fluid in a main beaker and mixed together using a pro mixer manufactured by

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Abstract

La présente invention concerne des compositions topiques contenant des particules solides qui sont stabilisées par encapsulation dans une matrice de silicone réticulée. Les particules stabilisées présentent un potentiel électrique suffisant pour empêcher les particules de pénétrer dans la peau. Les particules peuvent être utilisées aisément soit seules, soit en combinaison avec d'autres principes actifs de soins de la peau afin de former des compositions topiques à stabilité et performances améliorées.
PCT/US2013/049161 2012-07-09 2013-07-02 Compositions comprenant des particules solides encapsulées dans une matrice de silicone réticulée, et procédés de fabrication de celles-ci WO2014011456A1 (fr)

Priority Applications (6)

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JP2015521658A JP2015522071A (ja) 2012-07-09 2013-07-02 架橋シリコーンマトリックス中に封入された固体粒子を含む組成物、及びその作製方法
KR20157000194A KR20150018868A (ko) 2012-07-09 2013-07-02 가교 실리콘 매트릭스 내에 캡슐화된 고체 입자를 포함하는 조성물, 및 그의 제조 방법
AU2013288950A AU2013288950A1 (en) 2012-07-09 2013-07-02 Compositions comprising solid particles encapsulated in a cross-linked silicone matrix, and methods of making the same
EP13817152.5A EP2869812A4 (fr) 2012-07-09 2013-07-02 Compositions comprenant des particules solides encapsulées dans une matrice de silicone réticulée, et procédés de fabrication de celles-ci
CA2877317A CA2877317A1 (fr) 2012-07-09 2013-07-02 Compositions comprenant des particules solides encapsulees dans une matrice de silicone reticulee, et procedes de fabrication de celles-ci
CN201380036884.XA CN104640535A (zh) 2012-07-09 2013-07-02 包含包封在交联硅酮基质中的固体粒子的组合物及其制造方法

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WO2014011456A1 (fr) 2014-01-16
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