WO2002003930A2 - Methods of enhancing delivery of oil-soluble skin care actives - Google Patents
Methods of enhancing delivery of oil-soluble skin care actives Download PDFInfo
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- WO2002003930A2 WO2002003930A2 PCT/US2001/021602 US0121602W WO0203930A2 WO 2002003930 A2 WO2002003930 A2 WO 2002003930A2 US 0121602 W US0121602 W US 0121602W WO 0203930 A2 WO0203930 A2 WO 0203930A2
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—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
- A61K8/895—Polysiloxanes containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone
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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
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
-
- 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
- A61K8/06—Emulsions
- A61K8/064—Water-in-oil emulsions, e.g. Water-in-silicone emulsions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—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
- A61K8/894—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- 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
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- 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
- A61Q19/08—Anti-ageing preparations
Definitions
- oil-soluble actives such as terpene alcohols, phytosterols, anti-acne actives, beta-hydroxy acids, vitamin B 3 compounds, retinoids, anti-oxidants/radical scavengers, chelators, flavonoids, anti-inflammatory agents, anti- cellulite, and topical anesthetics, that are known to provide skin benefits.
- Extremely popular are oil-in-water and water-in-oil emulsion compositions that may include a variety of oil-soluble skin care actives in the oil phase of the emulsion.
- the oil phase is comprised of organic oils, such as mineral oil.
- water-in-oil emulsion compositions tend to impart an oily feel to the skin and are thus undesirable from a consumer standpoint.
- oil-soluble skin care actives are present in the oil phase of an oil- in-water or water-in-oil emulsion, it is often difficult to formulate such that the actives leave ("partition out of) the oil phase when the composition is applied to the skin. Therefore, less of the active present in the composition is actually delivered into the skin and the efficacy of such oil-soluble skin care actives is limited.
- Silicone provides a smooth, non-oily feel to the skin.
- the broad class of silicone elastomers including both emulsifying and non-emulsifying silicone elastomers is well-known in the art for formulating stable skin care compositions with a variety of benefits. See, e.g., U.S. Patents Nos. 5,412,004, U.S. 5,654,362, 5,889,108, and 5,811,487.
- Specific combinations of silicone elastomers are also known, such as the combination taught by U.S. Patent 6,221,979, for solubilizing water-soluble and oil-soluble skin care actives in order to achieve a uniform composition.However, oil-soluble skin care actives are poorly soluble in silicone.
- the present invention relates to topical water-in-oil compositions useful for enhancing the delivery of oil-soluble skin care actives.
- the compositions comprise a silicone oil, a silicone elastomer and an oil-soluble skin care active.
- the oil-soluble skin care active is selected from terpene alcohols, phytosterols, anti-acne actives, beta-hydroxy acids, vitamin B 3 compounds, retinoids, anti-oxidants/radical scavengers, chelators, flavonoids, anti-inflammatory agents, anti-cellulite, topical anesthetics, and mixtures thereof.
- the present invention also relates to methods of enhancing the delivery of oil-soluble skin care actives into the skin.
- compositions of the present invention can include, consist essentially of, or consist of, the components of the present invention as well as other ingredients described herein.
- consisting essentially of means that the composition or component may include additional ingredients, but only if the additional ingredients do not materially alter the basic and novel characteristics of the claimed compositions or methods.
- the skin care actives useful herein can be categorized by the benefit they provide or by their postulated mode of action. However, it is to be understood that the actives useful herein can in some instances provide more than one benefit or operate via more than one mode of action. Therefore, classifications herein are made for the sake of convenience and are not intended to limit the active to that particular application or applications listed.
- safe and effective amount means an amount of a compound or composition sufficient to significantly induce a positive benefit, preferably a positive keratinous tissue appearance or feel benefit, or positive hair appearance or feel benefit, including independently or in combinations the benefits disclosed herein, but low enough to avoid serious side effects, i.e., to provide a reasonable benefit to risk ratio, within the scope of sound judgment of the skilled artisan.
- “Signs of skin aging” include, but are not limited to, all outward visibly and tactilely perceptible manifestations as well as any other macro or micro effects due to skin aging. Such signs may be induced or caused by intrinsic factors or extrinsic factors, e.g., chronological aging and/or environmental damage.
- oil-soluble skin care actives present in skin care compositions (for example, moisturizing creams and lotions) to provide skin care benefits such as regulating the condition of skin.
- skin care compositions for example, moisturizing creams and lotions
- the use of a silicone elastomer enhances the delivery potential of oil-soluble skin care actives and thereby increases the efficacy of a particular active.
- the present invention is also useful for therapeutically regulating visible and/or tactile discontinuities in mammalian skin, including discontinuities in skin texture and color. For example, the apparent diameter of pores decreases, the apparent height of tissue immediately proximate to pore openings approaches that of the interadnexal skin, the skin tone/color becomes more uniform, and/or the length, depth, and/or other dimension of lines and/or wrinkles are decreased.
- the compositions of the present invention are also useful for regulating the condition of skin and especially for regulating keratinous tissue condition. Regulation of skin condition, namely mammalian and in particular human skin condition, is often required due to conditions which may be induced or caused by factors internal and/or external to the body.
- regulating skin condition includes prophylactically regulating and/or therapeutically regulating skin condition, and may involve one or more of the following benefits: thickening of skin (i.e., building the epidermis and/or dermis and/or sub-dermal (e.g., subcutaneous fat or muscle) layers of the skin and where applicable the keratinous layers of the nail and hair shaft) to reduce skin atrophy, increasing the convolution of the dermal-epidermal border (also known as the rete ridges), preventing loss of skin elasticity (loss, damage and/or inactivation of functional skin elastin) such as elastosis, sagging, loss of skin recoil from deformation; non-melanin skin discoloration such as under eye circles, blotching (e.g., uneven red coloration due to
- prophylactically regulating skin condition includes delaying, minimizing and/or preventing visible and/or tactile discontinuities in skin (e.g., texture irregularities in the skin which may be detected visually or by feel).
- therapeutically regulating skin condition includes ameliorating, e.g., diminishing, minimizing and/or effacing, discontinuities in skin.
- compositions of the present invention provide additional benefits, including stability, absence of significant (consumer-unacceptable) skin irritation and good aesthetics.
- a water-in-silicone composition containing silicone elastomers in the oil phase provides enhanced delivery of oil-soluble skin care actives, such as terpene alcohols, phytosterols, anti- acne actives, beta-hydroxy acids, vitamin B 3 compounds, retinoids, anti-oxidants/radical scavengers, chelators, flavonoids, anti-inflammatory agents, anti-cellulite, and topical anesthetics into the skin.
- oil-soluble skin care actives such as terpene alcohols, phytosterols, anti- acne actives, beta-hydroxy acids, vitamin B 3 compounds, retinoids, anti-oxidants/radical scavengers, chelators, flavonoids, anti-inflammatory agents, anti-cellulite, and topical anesthetics into the skin.
- the oil-soluble skin care active may be stably formulated into the silicone oil phase with the aid of the silicone elastomer, that the presence of both a silicone oil and silicone elastomer create a non-preferred environment for the oil-soluble skin care active. Therefore, upon application of the composition to the skin, the oil-soluble skin care active partitions out of the silicone elastomer and is delivered into the skin. The partitioning out effect leads to greater delivery of the oil-soluble active into the skin than if the active was present in a conventional oil phase.
- the present invention also relates to methods of enhancing the penetration of oil-soluble skin care actives by applying to the skin, a composition containing silicone elastomers.
- compositions of the present invention contain a silicone oil, a silicone elastomer, and an oil-soluble skin care active.
- Preferred compositions of the present invention are water-in- silicone oil emulsion compositions containing a silicone elastomer and an oil-soluble skin care active in the continuous oil phase.
- compositions herein may also include a wide variety of other ingredients.
- the compositions of the present invention are described in detail hereinafter.
- compositions of the present invention contain a safe and effective amount of an oil- soluble skin care active.
- An "oil-soluble active” may be defined as any active material that is immiscible with water.
- the composition contains from about 0.001% to about 40%, by weight of the composition formed, of the oil-soluble skin care active, more preferably from about 0.01% to about 40%, even more preferably from about 0.05% to about 30%, and still more preferably from about 0.1% to about 20%, more preferably from about 0.1% to about 10%
- oil-soluble actives that may be used in the present invention include oil-soluble terpene alcohols, phytosterols, anti-acne actives, beta-hydroxy acids, vitamin B 3 compounds, retinoids, anti-oxidants/radical scavengers, chelators, flavonoids, anti- inflammatory agents, anti-cellulite agents, topical anesthetics, and mixtures thereof.
- a preferred oil-soluble skin care active for use herein is farnesol. a) Oil-soluble Terpene Alcohols, phytosterols, anti-acne actives, beta-hydroxy acids, vitamin B 3 compounds, retinoids, anti-oxidants/radical scavengers, chelators, flavonoids, anti- inflammatory agents, anti-cellulite agents, topical anesthetics, and mixtures thereof.
- a preferred oil-soluble skin care active for use herein is farnesol.
- Geraniol is the common name for the chemical known as 3,7-dimethyl-2,6-octadien-l-ol. As used herein, "geraniol” includes isomers and tautomers of such. Geraniol is commercially available from Aldrich Chemical Company (P. O. Box 2060, Milwaukee, WI). Suitable derivatives of geraniol include geranyl acetate, geranylgeraniol, geranyl pyrophosphate, and geranylgeranyl pyrophosphate, all of which are commercially available from Sigma Chemical Company, P. O. Box 14508, St. Louis, MO.
- Phytantriol is the common name for the chemical known as 3,7,1 l,15,tetramethylhexadecane-l,2,3,-triol.
- Phytantriol is commercially available from BASF (1609 Biddle Avenue, Whyandotte, MI).
- phytantriol is useful as a spider vessel/ red blotchiness repair agent, a dark circle/puffy eye repair agent, sallowness repair agent, a sagging repair agent, an anti-itch agent, a skin thickening agent, a pore reduction agent, oil/shine reduction agent, a post-inflammatory hyperpigmentation repair agent, wound treating agent, an anti-cellulite agent, and regulating skin texture, including wrinkles and fine lines.
- Phytosterols a spider vessel/ red blotchiness repair agent, a dark circle/puffy eye repair agent, sallowness repair agent, a sagging repair agent, an anti-itch agent, a skin thickening agent, a pore reduction agent, oil/shin
- oils-soluble vitamin compounds are useful as oil-soluble skin care actives herein.
- oil-soluble vitamin compounds include retinoids, vitamin B 3 compounds, vitamin C (e.g. ascorbyl palmitate), vitamin D, vitamin K, vitamin E, and mixtures thereof.
- retinoids e.g. ascorbyl palmitate
- vitamin D e.g. ascorbyl palmitate
- vitamin K e.g. ascorbyl palmitate
- vitamin D e.g. ascorbyl palmitate
- vitamin D e.g. ascorbyl palmitate
- vitamin K e.g. ascorbyl palmitate
- vitamin D e.g. ascorbyl palmitate
- vitamin D e.g. ascorbyl palmitate
- vitamin D e.g. ascorbyl palmitate
- vitamin K e.g. ascorbyl palmitate
- vitamin D e.g. ascorbyl palmitate
- vitamin K e.g. ascorbyl palmitate
- vitamin K e.g
- retinoid includes all natural and/or synthetic analogs of Vitamin A or retinol-like compounds which possess the biological activity of Vitamin A in the skin as well as the geometric isomers and stereoisomers of these compounds.
- Non-limiting examples of retinoids useful herein include retinol, retinol esters (e.g., C2 - C22 alkyl esters of retinol, including retinyl palmitate, retinyl acetate, retinyl propionate), retinal, and/or retinoic acid (including all-trans retinoic acid and/or 13-cis-retinoic acid), preferably retinoids other than retinoic acid.
- retinoids include retinol, retinol esters (e.g., C2 - C22 alkyl esters of retinol, including retinyl palmitate, retinyl acetate, retinyl propionate), retinal,
- retinoids are retinol, retinyl palmitate, retinyl acetate, retinyl propionate, jetinal and combinations thereof, but any oil-soluble retinoid may be used herein.
- Oil-Soluble Vitamin B 3 Compounds Oil-soluble Vitamin B 3 compounds are particularly useful for regulating skin condition.
- Vitamin E and several derivatives thereof are known to be especially useful as anti-oxidants/radical scavengers.
- Such antioxidants/radical scavengers are especially useful for providing protection against UV radiation which can cause increased scaling or texture changes in the stratum corneum and against other environmental agents which can cause skin damage.
- Nonlimiting examples of oil soluble vitamin E compounds include tocopherol (vitamin E), tocopherol sorbate, tocopherol acetate, and other esters of tocopherol.
- Preferred anti-oxidants/radical scavengers are selected from tocopherol sorbate, tocopherol acetate, and mixtures thereof. Also useful herein are the class of materials, tocotrienols, which are related to vitamin E. d) Anti-Acne Actives
- Nonlimiting examples of oil-soluble beta-hydroxy acids include salicylic acid and derivatives thereof such as the octanoyl derivative. Beta-hydroxy acids are known to provide anti-acne and anti-aging benefits. f) Chelators
- chelator or “chelating agent” means an active agent capable of removing a metal ion from a system by forming a complex so that the metal ion cannot readily participate in or catalyze chemical reactions.
- the inclusion of a chelating agent is especially useful for providing protection against UV radiation which can contribute to excessive scaling or skin texture changes and against other environmental agents which can cause skin damage.
- Flavonoid compounds are broadly disclosed in U.S. Patents 5,686,082 and 5,686,367, both of which are herein incorporated by reference.
- Nonlimiting examples of flavonoids useful herein include isoflavones, flavanones selected from the group consisting of unsubstituted flavanones, mono-substituted flavanones, and mixtures thereof; chalcones selected from the group consisting of unsubstituted chalcones, mono-substituted chalcones, di-substituted chalcones, tri- substituted chalcones, and mixtures thereof; flavones selected from the group consisting of unsubstituted flavones, mono-substituted flavones, di-substituted flavones, and mixtures thereof; one or more isoflavones; coumarins selected from the group consisting of unsubstituted coumarins, mono-substituted cou
- suitable flavonoids include, but are not limited to, unsubstituted flavanone, mono-hydroxy flavanones (e.g., 2'-hydroxy flavanone, 6-hydroxy flavanone, 7-hydroxy flavanone, etc.), mono-alkoxy flavanones (e.g., 5-methoxy flavanone, 6-methoxy flavanone, 7- methoxy flavanone, 4'-methoxy flavanone, etc.), unsubstituted chalcone (especially unsubstituted trans-chalcone), mono-hydroxy chalcones (e.g., 2'-hydroxy chalcone, 4'-hydroxy chalcone, etc.), di-hydroxy chalcones (e.g., 2',4-dihydroxy chalcone, 2',4'-dihydroxy chalcone, 2,2'-dihydroxy chalcone, 2' ,3-dihydroxy chalcone, 2',5'-dihydroxy chalcone, etc
- unsubstituted flavanone Preferred for use herein are unsubstituted flavanone, methoxy flavanones, unsubstituted chalcone, 2' ,4-dihydroxy chalcone, isoflavones, and mixtures thereof. Most preferred are unsubstituted flavanone, unsubstituted chalcone (especially the trans isomer), isoflavones, and mixtures thereof.
- Flavonoid compounds useful herein are commercially available from a number of sources, e.g., Indofine Chemical Company, Inc. (Somerville, New Jersey), Steraloids, Inc. (Wilton, New Hampshire), NovaSoy from Archer Daniels Midland Co. (Decatur, JJ.linois),.and Aldrich Chemical Company, Inc. (Milwaukee, Wisconsin).
- Nonlimiting examples of oil-soluble anti-inflammatory agents useful herein include steroidal anti- inflammatory agents, such as the corticosteroids (e.g. hydrocortisone), and oil soluble nonsteroidal anti-inflammatory agents, such as the propionic acid derivatives (e.g. ibuprofen, naproxen, and/or ketoprofen). Mixtures of oil-soluble anti-inflammatory agents may also be employed, as well as the dermatologically acceptable salts and esters of these agents. For example, etofenamate, a flufenamic acid derivative, is particularly useful for topical application.
- Non-limiting examples of so-called "natural” anti-inflammatory agents useful herein include those obtained as an extract by suitable physical and/or chemical isolation from natural sources (e.g., plants, fungi, by-products of microorganisms) or can be synthetically prepared.
- natural sources e.g., plants, fungi, by-products of microorganisms
- candelilla wax, bisabolol (e.g., alpha bisabolol), and/or plant sterols (e.g., phytosterol) may be used.
- oil-soluble anti-cellulite skin care actives useful herein include the oil soluble xanthine compounds such as caffeine. j) Topical Anesthetics
- Non-limiting examples of oil-soluble topical anesthetic drugs include benzocaine, lidocaine, and pharmaceutically acceptable salts thereof.
- compositions of the present invention also include from about 0.1% to about 30%, by weight of the composition, of a silicone elastomer component.
- the composition includes from about 0.1% to about 30%, more preferably from about 0.5% to about 10%, by weight of the composition, of the silicone elastomer component All such percentages as they pertain to the silicone elastomer are based on the amount of elastomer and therefore, do not include carriers or by-products that may be included in commercially available materials.
- Commercially available silicone elastomers are often introduced into the overall composition in solution with a silicone oil. Such silicone oil amounts are considered in the overall percentages of silicone oil present in the compositions of the present invention.
- addition reaction-curing organopolysiloxane compositions which cure under platinum metal catalysis by the addition reaction between SiH-containing diorganopolysiloxane and organopolysiloxane having silicon- bonded vinyl groups; condensation-curing organopolysiloxane compositions which cure in the presence of an organotin compound by a dehydrogenation reaction between hydroxyl-terminated diorganopolysiloxane and SiH-containing diorganopolysiloxane; condensation-curing organopolysiloxane compositions which cure in the presence of an organotin compound or a titanate ester, by a condensation reaction between an hydroxyl-terminated diorganopolysiloxane and a hydrolyzable organosilane (this condensation reaction is exemplified by dehydration, alcohol-liberating, oxime-liberating, amine-liberating, amide-liberating, carboxyl-liberating, and ketone-
- component (C) a platinum-type catalyst.
- component (A) is the basic component of the silicone elastomer-generating organopolysiloxane, and curing proceeds by the addition reaction of this component with component (B) under catalysis by component (C).
- This component (A) must contain at least 2 silicon-bonded lower alkenyl groups in each molecule; an excellent cured product will not be obtained at few than two lower alkenyl groups because a network structure will not be formed.
- Said lower alkenyl groups are exemplified by vinyl, allyl, and propenyl. While the lower alkenyl groups can be present at any position in the molecular, their presence at the molecular terminals is preferred.
- Component (B) is an organopolysiloxane having at least 2 silicon-bonded hydrogen atoms in each molecule and is a crosslinker for component (A). Curing proceeds by the addition reaction of the silicon-bonded hydrogen atoms in this component with the lower alkenyl groups in component (A) under catalysis by component (C).
- This component (B) must contain at least 2 silicon-bonded hydrogen atoms in each molecule in order to function as a crosslinker. Furthermore, the sum of the number of alkenyl groups in each molecule of component (A) and the number of silicon-bonded hydrogen atoms in each molecule of component (B) is to be at least 5. Values below 5 should be avoided because a network structure is then essentially not formed.
- this component may be any of straight chain, branch-containing straight chain, cyclic, etc.
- the molecular weight of this component is not specifically restricted, but it is preferred that the viscosity at 25 degrees Centigrade be 1 to 50,000 centistokes in order to obtain good miscibility with component (A). It is preferred that this component be added in a quantity such that the molar ratio between the total quantity of silicon-bonded hydrogen atoms in the instant component and the total quantity of all lower alkenyl groups in component (A) falls within the range of (1.5:1) to (20:1). It is difficult to obtain good curing properties when this molar ratio falls below 0.5:1.
- Component (C) is a catalyst of the addition reaction of silicon-bonded hydrogen atoms and alkenyl groups, and is concretely exemplified by chloroplatinic acid, possibly dissolved in an alcohol or ketone and this solution optionally aged, chloroplatinic acid-olefin complexes, chloroplatinic acid-alkenylsiloxane complexes, chloroplatinic acid-diketone complexes, platinum black, and carrier-supported platinum.
- the silicone elastomers of the present invention may be further processed by subjecting them to a high shear (approximately 5,000 psi) treatment in the presence of a solvent for the silicone elastomer via a Sonolator with or without recycling in from 1 to 60 passes in order to result in a particular average particle size of silicone elastomer. Less than 10 passes results in an average particle size ranging from about 20 to 200 microns. From 10 to 60 passes results in an average particle size of less than 20 microns as measured by the Horiba LA-910. As used herein, the term "particle size" of the elastomer represents the elastomer particle size in its swelled state.
- compositions of the present invention contain a safe and effective amount of a silicone oil.
- the composition contains from about 5% to about 99%, by weight of the composition formed, of the silicone oil, more preferably from about 15% to about 95%, even more preferably from about 20% to about 90%, and still more preferably from about 25% to about 85%.
- compositions of the present invention may be anhydrous.
- “andhydrous” is meant that the composition contains less than 5% of water, preferably less than 1%.
- the composition may contain a combination of silicone oil, silicone elastomer, and oil- soluble active.
- Water-in-Silicone Emulsions contain a continuous silicone phase and a dispersed aqueous phase.
- the continuous silicone phase contains an organopolysiloxane oil for use in the composition.
- organopolysiloxane oil may be volatile, non-volatile, or a mixture of volatile and non-volatile silicones.
- nonvolatile refers to those silicones that are liquid under ambient conditions and have a flash point (under one atmospheric of pressure) of or greater than about 100°C.
- volatile refers to all other silicone oils.
- Suitable organopolysiloxanes can be selected from a wide variety of silicones spanning a broad range of volatilities and viscosities. Examples of suitable organopolysiloxane oils include polyalkylsiloxanes, cyclic polyalkylsiloxanes, and polyalkylarylsiloxanes.
- polyalkylsiloxanes include the polydimethylsiloxanes, which are also known as dimethicones, examples of which include the Vicasil® series sold by
- trimethylsiloxysilicate which is a polymeric material corresponding to the general chemical formula [(CH2)3SiO 2J ⁇ [Si ⁇ 2]y, wherein x is an integer from about 1 to about 500 and y is an integer from about 1 to about 500.
- a commercially available trimethylsiloxysilicate is sold as a mixture with dimethicone as Dow Corning® 593 fluid.
- compositions of the present invention may also comprise from about 10% to about 75%, by weight of the composition formed, of a dispersed aqueous phase.
- dispersed phase is a term well-known to one skilled in the art which means that the phase exists as small particles or droplets that are suspended in and surrounded by a continuous phase.
- the dispersed phase is also known as the internal or discontinuous phase.
- the dispersed aqueous phase is a dispersion of small aqueous particles or droplets suspended in and surrounded by the continuous silicone phase described hereinbefore.
- Emulsifying silicone elastomers are preferred for use herein and are discussed more fully above. Other silicone emulsifiers are also preferred. A combination of emulsifying silicone elastomer and silicone emulsifier is also useful herein.
- silicone emulsifiers are useful herein. These silicone emulsifiers are typically organically modified organopolysiloxanes, also known to those skilled in the art as silicone surfactants.
- Useful silicone emulsifiers include dimethicone copolyols. These materials are polydimethyl siloxanes which have been modified to include polyether side chains such as polyethylene oxide chains, polypropylene oxide chains, mixtures of these chains, and polyether chains containing moieties derived from both ethylene oxide and propylene oxide.
- Other examples include alkyl-modified dimethicone copolyols, i.e., compounds which contain C2-C30 pendant side chains.
- Still other useful dimethicone copolyols include materials having various cationic, anionic, amphoteric, and zwitterionic pendant moieties.
- silicone surfactants as depicted in the structures in the previous paragraph wherein R ⁇ is:
- dimethicone copolyols useful herein sold by Dow Corning Corporation are Dow Corning® 190, 193, Q2-5220, 2501 Wax, 2-5324 fluid, and 3225C (this later material being sold as a mixture with cyclomethicone). Cetyl dimethicone copolyol is commercially available as a mixture with polyglyceryl-4 isostearate (and) hexyl laurate and is sold under the tradename ABIL® WE-09 (available from Goldschmidt).
- Cetyl dimethicone copolyol is also commercially available as a mixture with hexyl laurate (and) polyglyceryl-3 oleate (and) cetyl dimethicone and is sold under the tradename ABIL® WS-08 (also available from Goldschmidt).
- dimethicone copolyols also include lauryl dimethicone copolyol, dimethicone copolyol acetate, diemethicone copolyol adipate, dimethicone copolyolamine, dimethicone copolyol behenate, dimethicone copolyol butyl ether, dimethicone copolyol hydroxy stearate, dimethicone copolyol isostearate, dimethicone copolyol laurate, dimethicone copolyol methyl ether, dimethicone copolyol phosphate, and dimethicone copolyol stearate. See International Cosmetic Ingredient Dictionary. Fifth Edition. 1993.
- non-silicone-containing emulsifiers useful herein are various non-ionic and anionic emulsifying agents such as sugar esters and polyesters, alkoxylated sugar esters and polyesters, C1-C30 fatty acid esters of C1-C30 fatty alcohols, alkoxylated derivatives of C1-C30 fatty acid esters of C1-C30 fatty alcohols, alkoxylated ethers of C1-C30 fatty alcohols, polyglyceryl esters of C1-C30 fatty acids, C1-C30 esters of polyols, C1-C30 ethers of polyols, alkyl phosphates, polyoxyalkylene fatty ether phosphates, fatty acid amides, acyl lactylates, soaps, and mixtures thereof.
- non-ionic and anionic emulsifying agents such as sugar esters and polyesters, alkoxylated sugar esters and polyesters, C1-C30 fatty
- Nonlimiting examples of suitable non-silicone-containing emulsifiers for use herein include: polyethylene glycol 20 sorbitan monolaurate (Polysorbate 20), polyethylene glycol 5 soya sterol, Steareth-20, Ceteareth-20, PPG-2 methyl glucose ether distearate, Ceteth-10, Polysorbate 80, cetyl phosphate, potassium cetyl phosphate, diethanolamine cetyl phosphate, Polysorbate 60, glyceryl stearate, PEG- 100 stearate, polyoxyethylene 20 sorbitan trioleate (Polysorbate 85), sorbitan monolaurate, polyoxyethylene 4 lauryl ether sodium stearate, polyglyceryl-4 isostearate, hexyl laurate, steareth-20, ceteareth-20, PPG-2 methyl glucose ether distearate, ceteth-10, diethanolamine cetyl phosphate, glyceryl stearate, PEG-
- a safe and effective amount of a desquamation active may be added to the compositions of the present invention, preferably from about 0.1% to about 10%, more preferably from about 0.2% to about 5%, even more preferably from about 0.5% to about 4%, by weight of the composition.
- Desquamation actives enhance the skin appearance benefits of the present invention. For example, the desquamation actives tend to improve the texture of the skin (e.g., smoothness).
- One desquamation system that is suitable for use herein contains sulfhydryl compounds and zwitterionic surfactants and is described in U.S. Patent No. 5,681,852, to Bissett, incorporated herein by reference.
- ethane thiol hydroxy acids (e.g., alpha- hydroxy acids such as lactic acid and glycolic acid or beta-hydroxy acids), phytic acid, lipoic acid; lysophosphatidic acid, skin peel agents (e.g., phenol and the like) which enhance the keratinous tissue appearance benefits of the present invention, especially in regulating keratinous tissue condition, e.g., skin condition.
- hydroxy acids e.g., alpha- hydroxy acids such as lactic acid and glycolic acid or beta-hydroxy acids
- phytic acid e.g., phytic acid
- lipoic acid e.g., lysophosphatidic acid
- skin peel agents e.g., phenol and the like
- compositions of the present invention may contain a safe and effective amount of one or more water-soluble vitamins.
- water-soluble vitamins include, but are not limited to, water-soluble versions of vitamin B, vitamin B derivatives, vitamin C, vitamin C derivatives, vitamin K, vitamin K derivatives, vitamin D, vitamin D derivatives, vitamin E, vitamin E derivatives, and mixtures thereof.
- Vitamin B 3 Compounds
- compositions of the present invention may contain a safe and effective amount of a vitamin B3 compound.
- the compositions preferably contain from about 0.01% to about 50%, more preferably from about 0.1% to about 10%, still more preferably from about 1% to about 5%, and still more preferably from about 2% to about 5%, by weight of the composition, of the vitamin B3 compound.
- compositions of the present invention may include a safe and effective amount of an anti-oxidant/radical scavenger, preferably from about 0.1% to about 10%, more preferably from about 1% to about 5%, of the composition.
- the anti-oxidant/radical scavenger is especially useful for providing protection against UV radiation which can cause increased scaling or texture changes in the stratum corneum and against other environmental agents which can cause skin damage.
- a safe and effective amount of a skin soothing or skin healing active may be added to the present composition, preferably, from about 0.1% to about 30%, more preferably from about 0.5% to about 20%, still more preferably from about 0.5% to about 10 %, by weight of the composition formed.
- Skin soothing or skin healing actives suitable for use herein include panthenoic acid derivatives (including panthenol, dexpanthenol, ethyl panthenol), aloe vera, allantoin, and dipotassium glycyrrhizinate.
- Polvacrylamide Polymers A non-limiting example of a polyacrylamide nonionic polymer useful herein is one given the CTFA designation polyacrylamide and isoparaffin and laureth-7, available under the Tradename Sepigel 305 from Seppic Corporation (Fairfield, NJ).
- compositions of the present invention are useful for enhancing the delivery of oil- soluble skin care actives into the skin.
- the percentage of oil-soluble active delivered to the skin dermis by the compositions of the present invention is greater than the percentage delivered by a single application of a conventional oil-in-water or water-in-oil emulsion wherein the active is in the oil phase.
- Measurement of such delivery enhancement may be completed by any conventional means of comparing the delivery of actives in standard topical skin care compositions. For example, ex-vivo skin penetration through cadaver skin using Franz cells is a standard methodology for measuring skin penetration of skin care actives.933
- Another approach to ensure a continuous exposure of the skin to at least a minimum level of the composition is to apply the compound by use of a patch applied, e.g., to the face.
- a patch applied e.g., to the face.
- the patch can be occlusive, semi-occlusive or non-occlusive and can be adhesive or non-adhesive.
- the composition can be contained within the patch or be applied to the skin prior to application of the patch.
- the patch can also include additional actives such as chemical initiators for exothermic reactions such as those described in U.S.
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Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
MXPA03000258A MXPA03000258A (es) | 2000-07-10 | 2001-07-09 | Metodos para mejorar el suministro de activos para el cuidado de la piel solubles en aceite. |
AU7193001A AU7193001A (en) | 2000-07-10 | 2001-07-09 | Methods of enhancing delivery of oil-soluble skin care actives |
JP2002508385A JP2004506613A (ja) | 2000-07-10 | 2001-07-09 | 油溶性スキンケア活性物質の放出増進方法 |
EP01950988A EP1313427A2 (en) | 2000-07-10 | 2001-07-09 | Methods of enhancing delivery of oil-soluble skin care actives |
CA002413276A CA2413276A1 (en) | 2000-07-10 | 2001-07-09 | Methods of enhancing delivery of oil-soluble skin care actives |
KR10-2003-7000291A KR20030020916A (ko) | 2000-07-10 | 2001-07-09 | 유용성 스킨 케어 활성제의 전달 향상 방법 |
AU2001271930A AU2001271930B2 (en) | 2000-07-10 | 2001-07-09 | Methods of enhancing delivery of oil-soluble skin care actives |
BR0112048-4A BR0112048A (pt) | 2000-07-10 | 2001-07-09 | Processos para aumentar a distribuição de substâncias ativas para cuidados com a pele solúveis em óleos |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US61326600A | 2000-07-10 | 2000-07-10 | |
US09/613,266 | 2000-07-10 | ||
US09/867,235 | 2001-05-29 | ||
US09/867,235 US20020022040A1 (en) | 2000-07-10 | 2001-05-29 | Methods of enhancing delivery of oil-soluble skin care actives |
Publications (2)
Publication Number | Publication Date |
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WO2002003930A2 true WO2002003930A2 (en) | 2002-01-17 |
WO2002003930A3 WO2002003930A3 (en) | 2002-05-23 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/US2001/021602 WO2002003930A2 (en) | 2000-07-10 | 2001-07-09 | Methods of enhancing delivery of oil-soluble skin care actives |
Country Status (9)
Country | Link |
---|---|
EP (1) | EP1313427A2 (ja) |
JP (1) | JP2004506613A (ja) |
CN (1) | CN1254230C (ja) |
AU (2) | AU7193001A (ja) |
BR (1) | BR0112048A (ja) |
CA (1) | CA2413276A1 (ja) |
CZ (1) | CZ200328A3 (ja) |
MX (1) | MXPA03000258A (ja) |
WO (1) | WO2002003930A2 (ja) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1704853A2 (en) * | 2005-03-24 | 2006-09-27 | Neutrogena Corporation | Water-in-silicone emulsion compositions |
EP1742646A1 (en) * | 2004-05-04 | 2007-01-17 | Queensland University of Technology | Functionalised siloxanes for scar tissue treatment |
WO2007148293A3 (en) * | 2006-06-22 | 2008-05-22 | Procter & Gamble | Personal care composition |
WO2008093299A2 (en) * | 2007-01-31 | 2008-08-07 | The Procter & Gamble Company | Oil-in-water personal care composition |
DE10340417C5 (de) * | 2003-09-02 | 2011-05-05 | Sebapharma Gmbh & Co. Kg | Kosmetische oder dermatologische Zubereitung mit Phytosterolen in Form einer W/O-Emulsion |
CN103385820A (zh) * | 2013-08-19 | 2013-11-13 | 广州博嘉生物科技有限公司 | 一种修护眼霜 |
US8892778B2 (en) | 2004-07-23 | 2014-11-18 | Citrix Systems, Inc. | Method and systems for securing remote access to private networks |
WO2017035195A1 (en) * | 2015-08-25 | 2017-03-02 | Silicone Arts Laboratories, Inc. | Compositions and methods for disguising dermatological blemishes |
EP3589279A4 (en) * | 2017-02-28 | 2020-12-30 | Topix Pharmaceuticals, Inc. | METHODS AND COMPOSITIONS FOR TREATMENT OF SKIN WITH RETINOID, AND RELATED DELIVERY SYSTEMS |
US11253463B2 (en) | 2018-01-08 | 2022-02-22 | Conopco, Inc. | Cosmetic compositions comprising silicone elastomer and emollient |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102342903B (zh) * | 2011-10-18 | 2013-02-27 | 浙江康恩贝健康产品有限公司 | 一种护肤组合物及其在预防和延缓皮肤衰老的用途与方法 |
EP2641585A1 (en) * | 2012-03-19 | 2013-09-25 | Coty Germany GmbH | Cosmetic skin composition with soothing effect and its use |
MX2020006170A (es) * | 2017-12-18 | 2020-11-24 | Ansella Therapeutics Inc | Composiciones y metodos para prevenir y tratar afecciones. |
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US5854336A (en) * | 1997-03-20 | 1998-12-29 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Process for preparing silicone elastomer compositions |
US5948855A (en) * | 1999-01-12 | 1999-09-07 | Dow Corning Corporation | Water-in-oil-in water emulsion |
Family Cites Families (1)
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US6045823A (en) * | 1996-09-19 | 2000-04-04 | Dragoco Gerberding & Co. Ag | Process for producing solid anhydrous composition, and pharmaceutical and cosmetic products comprising same |
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2001
- 2001-07-09 WO PCT/US2001/021602 patent/WO2002003930A2/en not_active Application Discontinuation
- 2001-07-09 MX MXPA03000258A patent/MXPA03000258A/es unknown
- 2001-07-09 CN CNB018137113A patent/CN1254230C/zh not_active Expired - Lifetime
- 2001-07-09 AU AU7193001A patent/AU7193001A/xx active Pending
- 2001-07-09 AU AU2001271930A patent/AU2001271930B2/en not_active Ceased
- 2001-07-09 BR BR0112048-4A patent/BR0112048A/pt not_active IP Right Cessation
- 2001-07-09 CA CA002413276A patent/CA2413276A1/en not_active Abandoned
- 2001-07-09 JP JP2002508385A patent/JP2004506613A/ja active Pending
- 2001-07-09 CZ CZ200328A patent/CZ200328A3/cs unknown
- 2001-07-09 EP EP01950988A patent/EP1313427A2/en not_active Withdrawn
Patent Citations (3)
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US5599533A (en) * | 1994-12-15 | 1997-02-04 | Estee Lauder, Inc. | Stable water-in-oil emulsion system |
US5854336A (en) * | 1997-03-20 | 1998-12-29 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Process for preparing silicone elastomer compositions |
US5948855A (en) * | 1999-01-12 | 1999-09-07 | Dow Corning Corporation | Water-in-oil-in water emulsion |
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Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10340417C5 (de) * | 2003-09-02 | 2011-05-05 | Sebapharma Gmbh & Co. Kg | Kosmetische oder dermatologische Zubereitung mit Phytosterolen in Form einer W/O-Emulsion |
AU2005237185B2 (en) * | 2004-05-04 | 2011-03-17 | Queensland University Of Technology | Functionalised siloxanes for scar tissue treatment |
EP1742646A1 (en) * | 2004-05-04 | 2007-01-17 | Queensland University of Technology | Functionalised siloxanes for scar tissue treatment |
EP1742646A4 (en) * | 2004-05-04 | 2010-11-03 | Univ Queensland | FUNCTIONALIZED SILOXANES FOR THE TREATMENT OF CICATRICIAL TISSUES |
US8892778B2 (en) | 2004-07-23 | 2014-11-18 | Citrix Systems, Inc. | Method and systems for securing remote access to private networks |
JP2006265253A (ja) * | 2005-03-24 | 2006-10-05 | Neutrogena Corp | シリコーン中水型エマルション組成物 |
EP1704853A3 (en) * | 2005-03-24 | 2007-01-24 | Neutrogena Corporation | Water-in-silicone emulsion compositions |
EP1704853A2 (en) * | 2005-03-24 | 2006-09-27 | Neutrogena Corporation | Water-in-silicone emulsion compositions |
WO2007148293A3 (en) * | 2006-06-22 | 2008-05-22 | Procter & Gamble | Personal care composition |
WO2008093299A3 (en) * | 2007-01-31 | 2010-01-21 | The Procter & Gamble Company | Oil-in-water personal care composition |
WO2008093299A2 (en) * | 2007-01-31 | 2008-08-07 | The Procter & Gamble Company | Oil-in-water personal care composition |
CN103385820A (zh) * | 2013-08-19 | 2013-11-13 | 广州博嘉生物科技有限公司 | 一种修护眼霜 |
WO2017035195A1 (en) * | 2015-08-25 | 2017-03-02 | Silicone Arts Laboratories, Inc. | Compositions and methods for disguising dermatological blemishes |
EP3589279A4 (en) * | 2017-02-28 | 2020-12-30 | Topix Pharmaceuticals, Inc. | METHODS AND COMPOSITIONS FOR TREATMENT OF SKIN WITH RETINOID, AND RELATED DELIVERY SYSTEMS |
US11266588B2 (en) | 2017-02-28 | 2022-03-08 | Topix Pharmaceuticals, Inc. | Skin treatment methods and compositions with retinoid and delivery systems thereof |
US11253463B2 (en) | 2018-01-08 | 2022-02-22 | Conopco, Inc. | Cosmetic compositions comprising silicone elastomer and emollient |
Also Published As
Publication number | Publication date |
---|---|
JP2004506613A (ja) | 2004-03-04 |
AU7193001A (en) | 2002-01-21 |
CZ200328A3 (cs) | 2003-04-16 |
CN1446072A (zh) | 2003-10-01 |
WO2002003930A3 (en) | 2002-05-23 |
CA2413276A1 (en) | 2002-01-17 |
CN1254230C (zh) | 2006-05-03 |
AU2001271930B2 (en) | 2005-12-08 |
BR0112048A (pt) | 2003-06-17 |
EP1313427A2 (en) | 2003-05-28 |
MXPA03000258A (es) | 2004-01-26 |
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