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    • 专利摘要:
    topical application of skin compositions having low pH. The present invention provides low pH compositions for topical administration to the skin. these comprise a buffering agent that has a pka of about 2.8 to about 4.2 and a cosmetically acceptable active ingredient that has a pka within about 1 unit of the pka of the buffering agent. the composition has a pH of about 3.3 to 4 and a buffering capacity of at least about 0.15. Also provided is a method of increasing the topical application of a cosmetically acceptable active ingredient having a pka of about 2.8 to about 4.
    公开号:BR102016017090B1
    申请号:R102016017090-7
    申请日:2016-07-22
    公开日:2022-01-18
    发明作者:Anne-Sophie Brillouet；Marisa DeVita Dufort；Ali Fassih；Devin L. Garcia；Ya-Ping Hu；Wen-Hwa Ting Li；Ramine Parsa；Jyotsna Paturi；Dianne Rossetti；Ying Sun；Janet Wangari-Talbot；Robert Wayne Yates
    申请人:Johnson & Johnson Consumer Inc；
    IPC主号:
    专利说明:

    FIELD OF THE INVENTION
    [001] The present invention relates to low pH compositions for topical administration to the skin. These comprise a buffering agent that has a pKa of about 2.8 to about 4.2 and a cosmetically acceptable active ingredient that has a pKa within about 1 unit of the pKa of the buffering agent. The composition has a pH of about 3.3 to about 4 and a buffering capacity of at least about 0.15. Also provided is a method of increasing the topical application of a cosmetically acceptable active ingredient that has a pKa of about 2.8 to about 4. BACKGROUND OF THE INVENTION
    [002] Hyaluronic acid or hyaluronan (HA) is a naturally occurring high molecular weight polysaccharide consisting of alternating monosaccharide units of N-acetyl-D-glucosamine and D-glucuronic acid linked by alternating glucosaminidic [beta] bonds 1-3 glucuronide and [beta] 1-4 glucosaminidic. It is a glycosaminoglycan (GAG) of common occurrence in the body. The molecular weight of linear hyaluronic acid is generally in the range of 50,000 to 8,000,000 or more. Hyaluronic acid is present in cartilage, joint fluids and skin tissue. It plays a role in many biological processes in the body, for example hydration and lubrication of tissues and is used to treat joint disorders, promote wound healing and vessel formation.
    [003] Hyaluronic acid has also been widely used in skin care. Commercially available cosmetic compositions generally contain linear hyaluronic acid as a moisturizing agent. However, the usefulness of linear hyaluronic acid is sometimes limited by the fact that it is rapidly degraded by hyaluronidase in the body.
    [004] Cross-linked hyaluronic acid provides better mechanical properties and in vivo residence time. For example, HyaCare® Filler CL, commercially available from Evonik Industries AG, is a wrinkle smoother comprising a water-in-oil emulsion containing small particles of cross-linked hyaluronic acid in a carrier of water, ethylhexyl stearate, di-isostearate /polyhydroxystearate/polyglyceryl-4 sebacate, and sodium isostearate. Hylasome® EG10, marketed by Vantage Specialty Ingredients, is another example of commercially available cross-linked hyaluronic acid for use in skin care.
    [005] Hyaluronic acid is also used commercially as an injectable filler to treat wrinkles and other signs of skin aging. However, injections are usually painful, particularly in the face, and must be given by a medical professional. A convenient and painless application of hyaluronic acid, particularly cross-linked hyaluronic acid, and other cosmetically acceptable large active ingredients by topical administration would be desirable. However, the stratum corneum of mammalian skin presents a considerable barrier against penetration. The ability of a substance applied to the skin surface to penetrate through the skin is inversely related to the thickness of the stratum corneum layer. In addition, the permeation of cross-linked hyaluronic acid and other large molecules into the skin is made more difficult due to its size. The large polymeric structure of hyaluronic acid that confers its beneficial effects also makes its topical administration difficult.
    [006] Compositions and methods of topical application of hyaluronic acid, including cross-linked hyaluronic acid, and other large molecules have now been identified. Specifically, the present inventors have found that low pH topical compositions that contain a buffering agent that has a pKa of about 2.8 to about 4.2 and provides a buffering capacity of at least 0.15, provide greater penetration of hyaluronic acid and other cosmetically acceptable large active ingredients that have pKa values of about 2.8 to about 4 into mammalian skin. Methods for enhancing the topical application of these cosmetically acceptable active ingredients are also provided. SUMMARY OF THE INVENTION
    [007] The present invention provides a composition for topical use comprising: (a) a buffering agent having a pKa of about 2.8 to about 4.2; and (b) a cosmetically acceptable active ingredient having a pKa within about 1 unit of the pKa of the buffering agent; wherein the composition has a pH of about 3.3 to about 4 and a buffering capacity of at least about 0.15.
    [008] The present invention also provides a composition for topical use comprising: (a) hyaluronic acid; (b) lactic acid; (c) stearet 10; (d) glycerol dilaurate; and (e) glycerin.
    [009] The present invention further provides a method for enhancing the topical application of a cosmetically acceptable active ingredient that has a pKa of about 2.8 to about 4, which comprises topically administering the cosmetically acceptable active ingredient in a composition that has a pH of about 3.3 to about 4, a buffering capacity of at least about 0.15, and it contains a buffering agent that has a pKa of about 2.8 to about 4.2.
    [0010] The present invention also provides a composition for topical use comprising: (a) lactic acid; (b) stearet 10; (c) glycerol dilaurate; and (d) glycerin. DETAILED DESCRIPTION OF THE INVENTION
    [0011] Unless otherwise indicated, all technical and scientific terms used in the present invention have the same meaning, as commonly understood by those skilled in the art to which the invention pertains. All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference.
    [0012] The term "buffering capacity" is a well-known chemical term, defined as the moles of an acid or base needed to change the pH of a solution by 1, divided by the change in pH and the volume of buffer in liters. It is a unitless number. A buffer resists changes in pH due to the addition of an acid or base despite consumption of the buffer.
    [0013] As used in the present invention, the term "apply topically" means to directly apply or spread onto the outer skin, scalp, or hair, for example, by the use of the hands or with an applicator such as a tissue, a ball applicator, or by sprinkling.
    [0014] As used in the present invention, the term "cosmetically acceptable" means that the ingredients that the term describes are suitable for use in contact with tissue (e.g. skin or hair) without toxicity, incompatibility, instability, irritation, or undue allergic reaction, or the like.
    [0015] As used in the present invention, a "cosmetically acceptable active agent" is a compound (e.g., a synthetic compound or a compound isolated from a natural source or a natural extract) that has a cosmetic or therapeutic effect on the skin or hair, including, but not limited to, anti-acne agents, shine control agents, antimicrobial agents, anti-inflammatory agents, anti-mycotic agents, anti-parasitic agents, external analgesics, sunscreens, sunscreens, antioxidants, keratolytic agents, surfactants, moisturizers, nutrients, vitamins, energy enhancers, anti-perspiration agents, astringents, deodorants, firming agents, anti-callosity agents and conditioning agents for hair and/or skin.
    [0016] The compositions of the present invention are suitable for treating signs of skin aging. As used in the present invention, the term "signs of skin aging" includes the presence of lines and wrinkles, loss of elasticity, uneven skin and blemishes. In a particularly preferred embodiment, the sign of aging is the presence of lines and wrinkles and/or loss of elasticity.
    [0017] As used in the present invention, the term "treating signs of skin aging" refers to smoothing, reducing, preventing, ameliorating, or eliminating the presence or signs of skin aging described above.
    [0018] As used in the present invention, the term "wrinkle" includes fine lines, fine wrinkles, or thick wrinkles. Examples of wrinkles include, but are not limited to, fine lines around the eyes (eg, "crow's feet"), forehead and cheek wrinkles, frowns and frown lines around the mouth.
    [0019] As used in the present invention, the term "loss of elasticity" includes loss of elasticity or structural integrity of the skin or tissue, which includes, but is not limited to, flabby, slack, or loose tissue. Loss of elasticity or tissue structure integrity can be a result of a number of factors, which include, but are not limited to, disease, aging, hormonal changes, mechanical trauma, environmental injury, or the result of an application of products such as a cosmetic or pharmaceutical product, to the fabric.
    [0020] As used in the present invention, the term "uneven skin" means a skin health problem associated with diffuse or mottled pigmentation, which can be classified as hyperpigmentation, such as post-inflammatory hyperpigmentation.
    [0021] As used in the present invention, the term "blemish" means a skin health problem associated with redness or erythema.
    [0022] As used in the present invention, the term "cosmetic" refers to a beautifying substance or preparation that preserves, restores, confers, simulates, or enhances the appearance of bodily beauty or appears to enhance beauty or youth, specifically when referring to to the appearance of the fabric or skin.
    [0023] As used in the present invention, the term "cosmetically effective amount" means an amount of a physiologically active compound or composition sufficient to treat one or more signs of skin aging, but low enough to avoid serious side effects. The cosmetically effective amount of the compound or composition will vary with the particular health condition being treated, the age and physical condition of the end user, the severity of the health condition being treated or prevented, the duration of treatment, the nature of other treatments, the specific compound or product/composition employed, the particular cosmetically acceptable vehicle used, and similar factors.
    [0024] The compositions of the invention are also useful for treating skin in need of hydration. As used herein, "skin in need of hydration" means skin that is, but is not limited to, lacking in moisture, lacking in sebum, cracked, dry, itchy, flaky, xerodermal, dehydrated, lacking in elasticity, lacking in elasticity. radiance, dull or lacking in lipids.
    [0025] Unless otherwise noted, a percentage or concentration refers to a percentage or concentration by weight (ie, % (by weight)). Unless otherwise noted, all tracks include endpoints, for example, "from 4 to 9" includes endpoints 4 and 9.
    [0026] The composition of the invention comprises: (a) a buffering agent that has a pKa of about 2.8 to about 4.2, and (b) a cosmetically acceptable active ingredient that has a pKa within about one unit of pKa of the buffering agent.
    [0027] Preferably, the pH of the composition is from about 3 to about 4. Preferably, the pH of the composition is from about 3.1 to about 3.5. Cosmetically acceptable active ingredient
    [0028] The cosmetically acceptable active ingredient has a pKa within about one unit of the pKa of the buffering agent used. In one embodiment, the cosmetically acceptable active ingredient has a pKa within about 0.7 unit of the pKa of the buffering agent.
    [0029] In one embodiment, the cosmetically acceptable active ingredient is selected from glycosaminoglycans, peptides, amino acids, starches, sugars and other cosmetically acceptable active agents that have a pKa in the range of about 2.8 to about 4.
    [0030] Preferably, the cosmetically acceptable active ingredient comprises a glycosaminoglycan.
    [0031] For example, the cosmetically acceptable active ingredient may comprise hyaluronic acid. Hyaluronic acid can be linear, cross-linked, or a mixture of linear and cross-linked hyaluronic acid. The molecular weight of hyaluronic acid can vary as desired from very low molecular weight to very high molecular weight.
    [0032] In a particular embodiment, the cosmetically acceptable active ingredient is or comprises cross-linked hyaluronic acid.
    [0033] In another embodiment, the cosmetically acceptable active ingredient comprises a mixture of linear and cross-linked hyaluronic acid.
    [0034] Hyaluronic acid has a pKa of 2.9.
    [0035] A commercially available cross-linked hyaluronic acid useful in the present invention is HyaCare® Filler CL from Evonik Industries AG. HyaCare® Filler CL is a high-purity, high-quality, fermentation-derived biopolysaccharide that is obtained by a solvent-free process. It is skin-identical hyaluronic acid with an average molecular weight of 700 kDa.
    [0036] Another commercially available cross-linked hyaluronic acid useful in the present invention is Hylasome® EG10, marketed by Vantage Specialty Ingredients.
    [0037] Cross-linked hyaluronic acid can be prepared as known in the art. For example, natural or synthetic sources of linear hyaluronic acid can be cross-linked with a variety of cross-linkers, including divinyl sulfone (DVS), formaldehyde, polyanhydrides, polyaldehydes, polyhydric alcohols, carbodiimides, epichlorohydrin, ethylene glycol diglycidyl ether , butanediol diglycidyl ether, polyglycerol polyglycidyl ether, polyethylene glycol, polypropylene glycol diglycidyl ether, bis- or poly-epoxy crosslinkers such as 1,2,3,4-diepoxybutane or 1,2,7,8-diepoxyoctane , or other crosslinkers known in the art. The degree of crosslinking can be adjusted as well as known in the art. Buffering agent and buffering capacity
    [0038] The buffering agent has a pKa of from about 2.8 to about 4.2, preferably from about 3.5 to about 4.
    [0039] The buffering agent can be, for example, lactic acid, glycolic acid, citric acid, malic acid, tartaric acid, gluconic acid, or gluconolactone. Preferably, the buffering agent is lactic acid.
    [0040] The amount of buffering agent in the composition is suitable to provide a composition with a buffering capacity greater than about 0.15, or greater than about 0.17, or greater than about 0.25 .
    [0041] Typically, the composition contains about 3 to about 12, or about 4 to about 8% by weight of buffering agent. emulsions
    [0042] In one embodiment, the composition is an emulsion comprising an aqueous phase, an oil phase, and a non-ionic lipid phase.
    [0043] The aqueous phase contains water.
    [0044] The aqueous phase may also contain structuring agents such as carbomers or other thickeners, for example xanthan gum, carrageenan gum, polyacrylate-13; polyisobutene; polysorbate-20; blends of polyacrylate-13/polyisobutylene/polysorbate-20 and the like, including mixtures thereof.
    [0045] Preferably, the composition comprises a thickener and the thickener is hydroxymethyl acrylate/sodium acryloyldimethyltaurate copolymer.
    [0046] The oil phase contains at least one cosmetically acceptable oil.
    [0047] As used in the present invention, the term "oil" means a hydrophobic material that can assist in balancing intermolecular forces to form micelle aggregates or to limit their size. Oils also serve as emollient ingredients to benefit product spreadability, skin feel and release of hydrophobic active ingredients such as, but not limited to, vitamins D, E, K and A, as well as sunscreens.
    [0048] Oils that are useful in the composition include a variety of hydrocarbon based oils, silicones, fatty acid derivatives, glycerides, vegetable oils, vegetable oil derivatives, alkyl esters, wax esters, wax derivatives of bee, sterols and phospholipids, as well as combinations thereof, in the range of approximately 20% to 50%, based on the total weight of the composition.
    [0049] Suitable hydrocarbon oils include petrolatum, mineral oil, microcrystalline waxes, squalene and combinations thereof.
    [0050] Silicone oils include dimethicone, dimethiconol, phenyl-dimethicone and cyclic polysiloxanes and combinations thereof. Silicone oils having viscosities of about 0.5 to about 1000,000 mm 2 /sec (from about 0.5 to about 100,000 ceSt) at 25°C may also be useful in the composition.
    [0051] Glycerides include castor oil, sunflower seed oil, coconut oil and its derivatives, vegetable oils and its derivatives, babassu oil, jojoba oil, shea butter, lanolin and combinations thereof.
    [0052] Alkyl ester oils include, but are not limited to, isopropyl esters of fatty acids and esters of long chain fatty acids. More preferably, the following alkyl esters are useful: isopropyl palmitate, isopropyl myristate, myristyl myristate, isohexyl palmitate, decyl oleate, isononyl isononanoate and combinations thereof.
    [0053] The non-ionic lipid phase comprises one or more non-ionic lipids such as glyceryl monoesters having a fatty acid chain containing from about 3 to about 50 carbon atoms, and preferably from about 10 to about 18 carbon atoms; glyceryl diesters having a fatty acid chain containing from about 5 carbon atoms to about 25 carbon atoms, and preferably from about 10 carbon atoms to about 18 carbon atoms; alkoxylated alcohols; alkoxylated alkylphenols; alkoxylated acids; alkoxylated amides; alkoxylated sugar derivatives; alkoxylated derivatives of natural oils or waxes; polyoxyethylene-polyoxypropylene block copolymers; polyoxyethylene ether fatty acids having a fatty acid chain containing from about 10 carbon atoms to about 18 carbon atoms; steroids; fatty acid esters of alcohols wherein the fatty acid is straight chain or branched having from about 10 carbon atoms to about 20 carbon atoms and the alcohol is straight chain or branched having from 1 to 10 carbon atoms; and mixtures thereof, wherein the alkoxylated lipids are alkoxylated with ethylene oxide or propylene oxide, with ethylene oxide being preferred.
    Examples of suitable glyceryl monoesters include, but are not limited to, glyceryl caprate, glyceryl caprylate, glyceryl cocate, glyceryl erucate, glyceryl hydroxystearate, glyceryl isostearate, glyceryl lanolate, glyceryl laurate , glyceryl linolate, glyceryl myristate, glyceryl oleate, glyceryl PABA, glyceryl palmitate, glyceryl ricinoleate, glyceryl stearate, glyceryl tiglycolate and mixtures thereof, being glyceryl laurate and glyceryl myristate glyceryl preferred.
    Examples of suitable glyceryl diesters include, but are not limited to, glyceryl dilaurate, glyceryl dioleate, glyceryl dimyristate, glyceryl disterate, glyceryl sesuoleate, glyceryl lactate stearate, and mixtures thereof, with glyceryl dilaurate and glyceryl dimyristate are preferred.
    [0056] Examples of suitable polyoxyethylene fatty ethers include, but are not limited to, polyoxyethylene cetyl/stearyl ether, polyoxyethylene cholesterol ether, polyoxyethylene laurate or dilaurate, polyoxyethylene stearate or distearate, lauryl ether or polyoxyethylene stearyl and mixtures thereof, wherein the polyoxyethylene "head" group ranges from about 2 to about 100 groups. Preferred polyoxyethylene fatty ethers include polyoxyethylene stearyl ether, polyoxyethylene myristyl ether, and polyoxyethylene lauryl ether having from about 3 to about 10 oxyethylene units.
    [0057] Examples of suitable steroids include, but are not limited to, cholesterol, betasitosterol, bisabolol and mixtures thereof.
    [0058] Examples of suitable fatty acid esters of alcohols include isopropyl myristate, aliphati-isopropyl n-butyrate, isopropyl n-hexanoate, isopropyl n-decanoate, iso-propyl palmitate, octidodecyl myristate.
    [0059] Exemplary alkoxylated alcohols useful as the nonionic lipid in the compositions of the invention have the structure shown in Formula I below: R5-(OCH2CH2)y—OH Formula I
    [0060] wherein R5 is a branched or unbranched alkyl group having from about 6 to about 22 carbon atoms and y is between about 4 and about 100, and preferably, between about 10 and about 100. A Preferred alkoxylated alcohol is the species where R5 is a lauryl group and y has a mean value of 23, which is known as lauret 23 and is available from ICI Americas, Inc. of Wilmington, Del., USA under the tradename " BRIJ 35".
    [0061] Another exemplary alkoxylated alcohol is an ethoxylated derivative of lanolin alcohol. Lanolin alcohol is a mixture of organic alcohols obtained from the hydrolysis of lanolin. An example of an ethoxylated derivative of lanolin alcohol is lanet-10, which is the polyethylene glycol ether of lanolin alcohol with an average ethoxylation value of 10.
    [0062] Another exemplary alkoxylated alcohol is polyoxypropylene-polyoxyethylene alkyl ether, for example PPG-12-Butet-16. This material is available from Amerchol Corp. of Edison, N.J., USA, under the tradename "UCON Fluid 50-HB-660."
    [0063] Another type of nonionic lipid includes alkoxylated alkylphenols, for example nonoxynol-14", available under the tradename "MAKON 14" from the Stepan Company of Northfield, Ill, USA.
    [0064] Another type of nonionic lipid includes alkoxylated acids, which are esters of an acid, most usually a fatty acid, with a polyalkylene glycol, eg PEG-8 laurate.
    [0065] Another type of non-ionic lipids includes alkoxylated amides, for example, PEG-6 cocoamide.
    [0066] Another type of non-ionic lipid includes the alkoxylated sugar derivatives, for example, polysorbate 20, a mixture of sorbitol laurate esters and sorbitol anhydrides, consisting predominantly of the monoester, condensed with about 20 moles of ethylene oxide. This material is available under the tradename "TWEEN 20" from ICI Americas of Wilmington, Del., USA.
    [0067] Another example of an alkoxylated sugar derivative useful in the compositions of the invention is PEG-20 methyl glucose sesquistearate, which is the polyethylene glycol ether of methyl glucose stearic acid sesquiester, contains an average of 20 moles of ethylene oxide and is available under the tradename "Glucamate SSE-20" from Amerchol Corp. of Edison, N.J., USA.
    [0068] Another type of non-ionic lipids includes the alkoxylated derivatives of natural oils and waxes. Examples of this class of material include PEG-40 lanolin, PEG-40 castor oil, and PEG-40 hydrogenated castor oil.
    [0069] Another type of nonionic lipids includes polyoxyethylene-polyoxypropylene block copolymers, for example Poloxamer 101 and Poloxamer 182.
    [0070] Preferred nonionic lipids include polyoxyethylene fatty ethers, glyceryl diesters and mixtures thereof. More preferred nonionic lipids include polyoxyethylene stearyl ether, polyoxyethylene myristyl ether and polyoxyethylene lauryl ether, glyceryl dilaurate, glyceryl dimyristate, glyceryl distearate and mixtures thereof, each ether having from about 5 to about 10 oxyethylene units.
    [0071] In an embodiment where reducing skin irritation is a concern, it is preferable to use a non-ionic lipid having a greater amount of carbon atoms in the hydrophilic head group portion or, alternatively, a non-ionic lipid having a greater amount of carbon atoms in the fatty acid portion of the hydrophobic chain. The latter can be obtained by increasing the amount of carbon atoms in the "head" group of, for example, a polyoxyethylene-10 stearyl ether from about 10 carbon atoms to from about 15 to 20 carbon atoms. The latter can be obtained by increasing the amount of carbon atoms in the 12-carbon fatty acid "tail" of, for example, glyceryl diesters, to from about 14 carbons to about 16 carbons.
    [0072] The composition of the present invention includes, based on the total weight of the composition, from about 1% to about 10%, and preferably from about 3% to about 7%, of the nonionic lipid.
    [0073] In a preferred embodiment, the non-ionic lipid phase comprises water, glyceride dilaurate, stearet-10 and glycerin.
    [0074] In one embodiment, the composition comprises hyaluronic acid, lactic acid, stearet 10, glycerol dilaurate and glycerin. Hyaluronic acid can be linear hyaluronic acid. Hyaluronic acid can be cross-linked hyaluronic acid. Hyaluronic acid can be a mixture of linear and cross-linked hyaluronic acid.
    [0075] In another embodiment, the composition comprises lactic acid, stearet 10, glycerol dilaurate and glycerin. Topical compositions
    [0076] The compositions of the present invention are applied topically to human skin or hair. Thus, the composition may further include a cosmetically acceptable topical carrier which may be from about 50% to about 99.99% by weight of the composition (e.g. from about 80% to about 99% by weight , of the composition). In a preferred embodiment of the invention, the cosmetically acceptable topical carrier includes water.
    [0077] The compositions can be used to manufacture a wide variety of product types including, but not limited to, lotions, creams, gels, sticks, sprays, ointments, bar and liquid soaps, shampoos and hair conditioners, hair products, pastes, foams, powders, mousses, shaving creams, wet wipes, tapes, hydrogels, film-forming products, facial and skin masks, films and makeup as foundations, and mascara. These types of products may contain various types of cosmetically acceptable topical vehicles, including, but not limited to, solutions, suspensions, emulsions such as microemulsions and nanoemulsions, gels, solids, and liposomes. The following are non-limiting examples of such carriers. Other carriers may be formulated by those skilled in the art.
    [0078] The compositions useful in the present invention may be formulated as solutions. Solutions typically include an aqueous or organic solvent (e.g., from about 50% to about 99.99%, or from about 90% to about 99% of a cosmetically acceptable aqueous or organic solvent). Examples of suitable organic solvents include propylene glycol, polyethylene glycol, polypropylene glycol, glycerol, 1,2,4-butanetriol, sorbitol esters, 1,2,6-hexanetriol, ethanol, and mixtures thereof.
    [0079] The compositions useful in the present invention may be formulated as a solution comprising an emollient. Such compositions preferably contain from about 2% to about 50% of one or more emollients. As used in the present invention, the term "emollients" refers to materials used for the prevention or relief of dryness, such as by preventing transepidermal water loss from the skin. Examples of emollients include, but are not limited to, those featured in the International Cosmetic Ingredient Dictionary and Handbook, editors Pepe, Wenninger, and McEwen, pages 2930-36 (The Cosmetic, Toiletry, and Fragrance Association, Washington, DC, 9th Edition, 2002 ) (hereinafter in the present document "ICI Manual"). Examples of particularly acceptable emollients include vegetable oils, mineral oils, fatty esters, and the like.
    [0080] A lotion can be produced from a solution. Lotions typically contain from about 1% to about 20% (e.g., from about 5% to about 10%) of one or more emollients, and from about 50% to about 90% (e.g., of about 60% to about 80%) water.
    [0081] Another type of product that can be formulated from a solution is a cream. A cream typically contains from about 5% to about 50% (e.g. from about 10% to about 20%) emollient(s) and from about 45% to about 85% (e.g. from about 50% to about 75%) water.
    [0082] The composition of the present invention may include water or, alternatively, may be anhydrous or an ointment that does not include water, but organic and/or silicone solvents, oils, lipids and waxes. An ointment may contain a simple base of animal or vegetable oils or semi-solid hydrocarbons. An ointment can contain from about 2% to about 10% emollient(s) plus about 0.1% to about 2% thickening agent(s). Examples of thickening agents include, but are not limited to, those presented in the ICI Handbook, pages 2979-84.
    [0083] The composition may be formulated as an emulsion. If the topical vehicle is an emulsion, from about 1% to about 10% (e.g., from about 2% to about 5%) of the topical vehicle contains an emulsifier(s). Emulsifiers can be non-ionic, anionic or cationic. Examples of emulsifiers include, but are not limited to, those presented in the ICI Manual pages 2962 to 71.
    [0084] Lotions and creams can be formulated as emulsions. Typically such lotions contain from 0.5% to about 5% of an emulsifier(s). These creams typically contain from about 1% to about 20% (e.g., from about 5% to about 10%) of an emollient(s); from about 20% to about 80% (e.g., from 30% to about 70%) water; and from about 1% to about 10% (e.g., from about 2% to about 5%) of emulsifier(s).
    [0085] Simple emulsion preparations for skin treatment, such as lotions and creams, of the oil-in-water and water-in-oil type are well known in the cosmetic art and are useful in the present invention. Multiphase emulsion compositions, such as the water-in-oil-in-water type or the oil-in-water-in-oil type, are also useful in the present invention. In general, such single or multiphase emulsions contain water, emollients and emulsifiers as essential ingredients.
    [0086] The compositions of this invention may also be formulated as a gel (e.g., an aqueous, alcoholic, aqueous-alcoholic, or oily gel using one or more suitable gelling agents). Suitable gelling agents for aqueous and/or alcoholic gels include, but are not limited to, natural gums, polymers and copolymers of acrylic acid and acrylate, and cellulose derivatives (e.g., hydroxymethylcellulose and hydroxypropylcellulose). Suitable gelling agents for oils (such as mineral oil) include, but are not limited to, hydrogenated butylene/ethylene/styrene copolymer and hydrogenated ethylene/propylene/styrene copolymer. Such gels typically contain between about 0.1% and 5% by weight of such gelling agents.
    [0087] The compositions of the present invention may also be formulated into a solid formulation (e.g., wax-based stick, soap bar composition, talc, or a talc-containing handkerchief).
    [0088] The compositions useful in the present invention may contain, in addition to the aforementioned components, a wide variety of additional oil-soluble materials and/or water-soluble materials conventionally used in compositions for use on the skin or hair, at levels established in the art. Additional cosmetically acceptable active agents
    [0089] In one embodiment, the composition contains an additional cosmetically acceptable active agent.
    [0090] In one embodiment, the additional agent is selected from, but not limited to, the group consisting of hydroxy acids, benzoyl peroxide, d-panthenol, octyl methoxycinimate, octyl salicylate, homosalate, avobenzone, carotenoids, retinoids such as retinol and retinyl palmitate, ceramides, polyunsaturated fatty acids, essential fatty acids, enzymes, enzyme inhibitors, minerals, hormones such as estrogens, steroids such as hydrocortisone, 2-dimethylaminoethanol, copper salts such as copper chloride, peptides including those containing copper, coenzyme Q10, amino acids such as proline, vitamins, lactobionic acid, acetyl-coenzyme A, niacin, riboflavin, thiamine, ribose, electron carriers such as NADH and FADH2, and other botanical extracts such as aloe vera, feverfew, oat flour and derivatives and mixtures thereof. The additional cosmetically active agent will typically be present in the composition of the invention in an amount of from about 0.001% to about 20% by weight of the composition, for example, from about 0.005% to about 10%, such as from about 0 .01% to about 5%.
    [0091] Examples of vitamins include, but are not limited to, vitamin A, B-complex vitamins such as vitamin B3, vitamin B5, and vitamin B12, vitamin C, vitamin K, and different forms of vitamin E such as alpha, beta, gamma or delta tocopherols or mixtures thereof, and derivatives thereof.
    [0092] Examples of hydroxy acids include, but are not limited to, glycolic acid, lactic acid, malic acid, salicylic acid, citric acid and tartaric acid.
    [0093] Examples of antioxidants include, but are not limited to, water-soluble antioxidants such as sulfhydryl compounds and derivatives thereof (e.g., sodium metabisulfite and N-acetyl-cysteine), lipoic acid and dihydrolipoic acid, resveratrol, lactoferrin , and ascorbic acid and ascorbic acid derivatives (e.g., ascorbyl palmitate and ascorbyl polypeptide). Oil-soluble antioxidants suitable for use in the compositions of this invention include, but are not limited to, butylated hydroxytoluene, retinoids (e.g., retinol and retinyl palmitate), tocopherols (e.g., tocopheryl acetate), tocotrienols, and ubiquinone. Natural extracts containing antioxidants suitable for use in the compositions of this invention include, but are not limited to, extracts containing flavonoids and isoflavonoids and their derivatives (e.g., genistein and diadzein), extracts containing resveratrol and the like. Examples of natural extracts include grape seed, green tea, pine cork, and propolis. Other materials
    [0094] Various other materials may also be present in the composition, as known in the art. These include humectants, pH adjusters, chelating agents (eg, EDTA), fragrances, dyes, and preservatives (eg, parabens).
    [0095] The composition, formulations and products containing such compositions of the present invention can be prepared using methodology well known to a person of ordinary skill in the art.
    [0096] The composition provides increased topical application of the cosmetically acceptable active ingredient by increasing its penetration through the stratum corneum. Method for increasing topical application
    [0097] In one embodiment, the invention provides a method for enhancing the topical application of a cosmetically acceptable active ingredient that has a pKa of about 2.8 to about 4, which comprises topically administering the cosmetically acceptable active ingredient in a composition. which has a pH of about 3.3 to about 4, a buffering capacity of at least about 0.15, and which contains a buffering agent that has a pKa of about 2.8 to about 4.2 .
    [0098] As used herein, the term "topical application" of an active ingredient means 1) penetration of the active ingredient into human skin, or 2) retention of the active ingredient into human skin, or 3) both penetration and retention of the active ingredient on human skin. The use of the method of the invention, preferably both in penetrating and retaining a cosmetically acceptable active ingredient in human skin, is intensified.
    [0099] For example, the topical application of a cosmetically acceptable active ingredient may be double or more compared to its topical application when contained in a composition that has a pH greater than 4, but is otherwise equal.
    [00100] Alternatively, the topical application of a cosmetically acceptable active ingredient may be double or more compared to its topical application when contained in a composition that does not contain the buffering agent which has a pKa of about 2.8 to about 4.2, but otherwise it's the same.
    [00101] In a preferred embodiment, the cosmetically acceptable active ingredient comprises hyaluronic acid. In particular, the hyaluronic acid may comprise linear hyaluronic acid, cross-linked hyaluronic acid, or a mixture of linear and cross-linked hyaluronic acid. For example, the cosmetically acceptable active ingredient may comprise cross-linked hyaluronic acid.
    [00102] For the purposes of the method of the invention, the penetration of hyaluronic acid is measured using the Hyaluronic Acid Penetration Test below, which measures the bioapplication of hyaluronic acid. Tissues equivalent to human epidermis (MatTek Corporation, EpiDerm-Epi-200) are used. Tissues equivalent to the epidermis are manipulated and cultured according to the supplier's instructions. A 6 µl sample of a test composition is applied topically to a tissue, which is then maintained in culture in a 5% CO 2 incubator, 37°C. The culture medium under the tissue is collected 24 hours after treatment and measured for the presence of HA using a Hyaluronan ELISA kit (Echelon, Inc., cat. #K-1200) following the manufacturer's instructions. To assess the presence of HA, the colorimetric change of the reagents is measured at 405 nm using a microplate reader (Versamax, Molecular Devices Inc.).
    [00103] The following non-limiting examples illustrate the invention in more detail. Example 1
    [00104] A series of inventive and comparative compositions were produced using the ingredients shown in Table 1. All inventive and comparative compositions consisted of three phases: a main aqueous phase, an oil phase and a non-ionic lipid phase. The compositions were prepared using the following procedure while varying the amounts of lactic acid (buffering agent) and sodium lactate (pH adjuster) as discussed in the examples below.


    [00105] To prepare the main phase (ingredients 1 to 5 in Table 1) of each composition, a mixing vessel was charged with purified water and mixing was started. The thickener or viscosity increasing agent (Sepimax C) was added to the vessel and mixed until fully dispersed. Once dispersed, the main phase was heated to 75 to 80°C. During heating, the chelating agent (disodium EDTA), moisturizer/humectant (glycerin) and the preservative (chlorphenesin) were added. The main phase was maintained at 75 to 80°C with continuous mixing until the phase formation step below.
    [00106] To prepare the oil phase (ingredients 6 to 16 in Table 1), a side container was loaded with emulsifiers/emulsion stabilizers (stearic acid, palmitic acid, sodium stearoyl lactylate, glyceryl stearate, PEG -100 stearate, stearyl alcohol and cetyl alcohol), which were mixed and heated to 75 to 80°C. Skin emollients/conditioners (C12-15 alkyl benzoate, dimethicone, propylene glycol isostearate, C12-15 alkyl lactate and cetyl lactate) were then added to the container and mixed until a uniform solution was obtained at a temperature of 75 to 80°C. Heating was continued until the temperature reached 80 to 85°C, at which point the oil phase was maintained for the phase formation step described below.
    [00107] To prepare the non-ionic lipid phase (ingredients 17 to 20 in Table 1), a vessel was charged with purified water, mixed on high and heated to 60 to 65°C while mixing into the non-ionic lipid ingredients (dilaurate of glyceride, POE - stearet-10 and glycerin) until uniform, then kept at 60 to 65°C until addition to the main phase.
    [00108] To complete the phase formation step, the main phase (75 to 80°C) and the oil phase (75 to 80°C) were combined by adding the oil phase to the main phase. The temperature was maintained at 75 to 80°C and the mixture was stirred until uniform. Once the phases were uniform, the container was cooled to 55 to 60°C, at which point Hyacare Filler CL (cross-linked hyaluronic acid (HA)) was added to the container and mixed until the ingredients were fully dispersed and uniform throughout. batch. The batch was further cooled to 50 to 55°C and the non-ionic lipid phase was added to the batch. The batch was then mixed until all ingredients were fully dispersed and uniform. Once uniform, the batch was cooled to 35 to 40°C and the buffering agent (lactic acid), preservative (phenoxyethanol; ethylhexylglycerin), propylene glycol and fragrance were added. The batch was mixed until uniform. The pH was slowly adjusted to the desired range using sodium lactate. Example 2
    [00109] Six compositions, 2A to 2F were prepared as described in Example 1 and tested for penetration of hyaluronic acid (HA) using the Hyaluronic Acid Penetration Test described above. The compositions were made without lactic acid and varying the pH values. All compositions had buffering capacities less than 0.002.
    [00110] Results are shown in Table 2. The highest percentage increase in HA penetration in the untreated sample was only 64% (2D Composition).
    Example 3
    [00111] Four compositions were prepared as described in Example 1 and tested for penetration of hyaluronic acid (HA) using the Hyaluronic Acid Penetration Test. The compositions had a fixed pH of 3.3, but different amounts of lactic acid and different buffering capacities.
    [00112] The results are shown in Table 3. The penetration of HA was clearly and directly dependent on the buffering capacity. Compositions 3A and 3B, having buffering capacities of less than 0.1, demonstrated increases in HA penetration of 10% and 119%, respectively. However, Compositions 4C and 4D according to the invention and having buffering capacities greater than 0.1 demonstrated HA penetration four and five times, respectively, greater than the untreated sample, and more than twice that of the untreated sample. achieved with Compositions 3A and 3B.
    Example 4
    [00113] Six compositions prepared according to Example 1 were tested for penetration of hyaluronic acid (HA) using the Hyaluronic Acid Penetration Test. Each of the compositions contained 6% by weight lactic acid but had pH values in the range of 3.0 to 6.0 and buffering capacities of 0.096 to 0.37.
    [00114] The results are shown in Table 4. There was a clear inverse relationship between HA penetration and pH.
    Example 5
    [00115] Four compositions prepared according to Example 1 were tested for penetration of hyaluronic acid (HA) using the Hyaluronic Acid Penetration Test. The compositions contained varying amounts of lactic acid, with buffering capacities from 0.001 to 0.021. Each composition had a pH of 6.
    [00116] The results are shown in Table 5. None of these compositions increased the penetration of hyaluronic acid by more than 18% (Composition 5D) over the untreated sample.
    Example 6
    [00117] This example demonstrates that other buffering agents can be used in accordance with the invention.
    [00118] Four compositions were prepared according to Example 1 using glycolic acid instead of lactic acid as the buffering agent. These were tested for hyaluronic acid (HA) penetration using the Hyaluronic Acid Penetration Test. Each composition had a pH of 3.3. The amount of glycolic acid and buffering capacities varied.
    [00119] The results are shown in Table 6. The penetration of HA depended on the amount of glycolic acid.
    [00120] Composition 6D was prepared with 6% glycolic acid and a pH of 6.0 (buffering capacity of 0.01), which demonstrated only a 14% increase in HA penetration over the untreated sample.
    Example 7
    [00121] The effects of pH on the skin were tested using compositions 3B and 3D. Each composition was applied to the forearm of three human volunteers, with a control formulation not otherwise buffered, but containing no lactic acid. Both test compositions had a pH of 3.3.
    [00122] Skin pH was measured before application and four hours after application using a Skin pH Meter 905 [Skin pH Meter] (Courage and Khazaka).
    [00123] After four hours, the skin pH was reduced by 0.593 pH units with Composition 3B, but 1.28 pH units with the buffered formulation of Composition 3D, indicating a greater ability of the buffered formula to overcome the tamponade system of the skin itself. The difference represents a skin acidity level about 5 times higher, as measured by H+ ions, for buffered versus non-buffered control.
    [00124] These data demonstrate the utility and benefit of a composition according to the invention for maintaining a low skin pH over time. Example 8
    [00125] A series of compositions according to the invention were prepared using the ingredients in Table 7. The various thickeners shown in Table 8 below were substituted in the compositions.


    [00126] Six formulations were prepared using the base formula above and substituting various thickeners as described in Table 8, which also demonstrates the penetration levels of HA.


    [00127] All six formulations were low pH formulas with buffering capacities of 0.26. All formulations applied HA to the skin; however, formulation 4 applied HA only modestly. Formulation 2 provided good application of HA to the skin as well as good esthetics.Example 9
    [00128] A daily use composition according to the invention containing sunscreens was prepared using the ingredients shown in Table 9 by the process described below.



    [00129] First, xanthan gum and glycerin were mixed in a side container.
    [00130] Next, the non-ionic lipid phase (ingredients 20 to 23) was prepared by mixing 9% water, glycerin, glyceryl dilaurate and stearet 10 in a mixing vessel, mixed on high and heated to 65°C.
    [00131] Then, to prepare the oil phase (ingredients 10 to 18), stearic acid, glyceryl stearate, PEG-100 stearate, cetyl alcohol, octisalate, Finsolv TN, Crodamol PMP, avobenzone, octocrylene and oxybenzone were added to mixing vessel, and heated to 75 to 80°C while blending. The temperature was maintained until they were ready for emusification.
    [00132] To prepare the main phase (ingredients 1 to 3), water and lactic acid were slowly added to a mixing vessel and mixed on high. Sclerotium gum was splattered. After obtaining a uniform mixture, the xanthan gum phase was added. The contents of the vessel were mixed until uniform, and then heated to 75 to 80°C, at which time disodium EDTA, chlorphenesin, Lexgard O and panthenol were added. The temperature was maintained at 75 to 80°C for five minutes.
    [00133] The emulsification was carried out at 75 to 80°C by first adding the oil phase to the main phase and mixing for five minutes, then cooling. During cooling, Hyacare Filler was added at 60°C. The non-ionic lipid phase was added at 50°C. Tocopheryl acetate and phenoxyethanol were added at 40°C and the resulting mixture was mixed until uniform. The batch was then cooled to 35°C.
    [00134] The pH of the composition was adjusted to 3.3 with sodium lactate, and q.s.p. up to 100% with purified water.
    [00135] The composition was tested for HA penetration using the Hyaluronic Acid Penetration Test, showing strong bioapplication of HA (863 ng/ml) compared to untreated (69 ng/ml).Example 10
    [00136] Two daily use compositions were prepared according to Example 9, except that one contained 0% lactic acid with a buffering capacity of < 0.001 (comparative composition 11A) and the other contained 6% lactic acid with a buffering capacity of < 0.001 (Comparative Composition 11A) buffering of 0.26 (inventive composition 11B). The pH of each composition was 3.3.
    [00137] The compositions were applied topically to tissues equivalent to human epidermis (MatTek Corporation, EpiDerm-Epi-200) as described in connection with the Hyaluronic Acid Penetration Test. Culture media under each tissue were collected at 1, 6 and 24 hours after treatment. The collected culture media were fixed in an acid-formalin solution. After fixation for 24 hours in the acid-formalin solution, the tissues were dehydrated and embedded in paraffin. 5 μm thick paraffin sections were made and the sections were then mounted on Superfrost® plus silanized glass slides. Hyaluronic acid immunostaining was performed on sections paraffinized with an antibiotinylated hyaluronic acid (HABP) (EMD Millipore) and amplified with a biotin/streptavidin system (Vector Laboratories) and revealed in blue color. Staining was assessed by microscopic observation with a Leitz microscope using a Leica DFC 320 camera and Image Pro Plus software (Media Cybernetics). To assess HA penetration, the intensity of exogenous HA revealed in blue color was quantified using Adobe Photoshop CS5 software (Adobe Systems Inc.). Data were expressed in relation to a scale of 256 colors.
    [00138] Tissue treated with inventive composition 11B at the 1 hour assessment time after treatment demonstrated HA remaining above the tissue and there was an absence of HA penetrated into the surface layers within the tissues. However, at 6 and 24 hours after treatment, the HA had completely penetrated the interior of the tissue, as revealed by the blue staining of the upper layers within the tissues and the disappearance of the blue staining above the tissues.
    [00139] In contrast, tissue treated with Comparative Composition 11A demonstrated staining of HA above the tissue and an absence of HA penetrated into the surface layers within the tissues at all assessment times.
    [00140] The results are shown in Table 10.

    [00141] This example demonstrates that the compositions according to the invention advantageously provide both penetration and tissue retention.
    权利要求:
    Claims (18)
    [0001]
    1. Topical composition, characterized in that it comprises: (a) from 3 to 6% by weight of a buffering agent having a pKa of 2.8 to 4.2; and (b) a cosmetically acceptable active ingredient comprising glycosaminoglycan and having a pKa within 1 unit of the pKa of the buffering agent; wherein the composition has a pH of 3.3 to 4 and a buffering capacity of at least 0.15 .
    [0002]
    2. Topical composition according to claim 1, characterized in that the cosmetically acceptable active ingredient has a pKa within 0.7 unit of the pKa of the buffering agent.
    [0003]
    3. Topical composition, according to claim 1, characterized in that the cosmetically acceptable active ingredient comprises hyaluronic acid.
    [0004]
    4. Topical composition, according to claim 1, characterized in that the cosmetically acceptable active ingredient comprises cross-linked hyaluronic acid.
    [0005]
    5. Topical composition, according to claim 1, characterized in that the buffering agent is selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, gluconic acid and gluconolactone.
    [0006]
    6. Topical composition, according to claim 1, characterized by the fact that the buffering agent is lactic acid.
    [0007]
    7. Topical composition according to claim 1, characterized in that it comprises: (a) hyaluronic acid; (b) from 3 to 6% by weight of lactic acid; (c) stearet 10; (d) glycerol dilaurate; and (e) glycerin, wherein the composition has a pH of 3.3 to 4 and a buffering capacity of at least 0.15.
    [0008]
    8. Topical composition, according to claim 7, characterized by the fact that hyaluronic acid comprises cross-linked hyaluronic acid.
    [0009]
    9. Topical composition, according to claim 7, characterized in that it additionally comprises a thickener selected from the group consisting of magnesium aluminum silicate, hydroxyethyl acrylate/sodium acryloyldimethyltaurate copolymer, xanthan gum, silica, cetyl hydroxyethyl cellulose, and polyacrylate-13/polyisobutylene/polysorbate-20 blend and mixtures thereof.
    [0010]
    10. Topical composition, according to claim 9, characterized in that the thickener comprises hydroxyethyl acrylate/sodium acryloyldimethyltaurate copolymer.
    [0011]
    11. Method for enhancing the topical application of a cosmetically acceptable active ingredient having a pKa of 2.8 to 4, characterized in that it comprises topical administration of the cosmetically acceptable active ingredient in a composition having a pH of 3.3 at 4, a buffering capacity of at least 0.15 and containing from 3 to 6% by weight of a buffering agent having a pKa of 2.8 to 4.2.
    [0012]
    12. Method according to claim 11, characterized in that said topical application is at least double compared to the topical application of the cosmetically acceptable active ingredient when contained in the composition having a pH greater than 4.
    [0013]
    13. Method according to claim 11, characterized by the fact that said topical application is at least double compared to the topical application of the cosmetically acceptable active ingredient when contained in the composition not containing said buffering agent.
    [0014]
    14. Method according to claim 11, characterized in that the cosmetically acceptable active ingredient comprises hyaluronic acid.
    [0015]
    15. Method according to claim 11, characterized in that the cosmetically acceptable active ingredient comprises cross-linked hyaluronic acid.
    [0016]
    16. Topical composition according to claim 1, characterized in that it comprises: (a) from 3 to 6% by weight of lactic acid; (b) stearet 10; (c) glycerol dilaurate; and (d) glycerin, wherein the composition has a pH of 3.3 to 4 and a buffering capacity of at least 0.15.
    [0017]
    17. Topical composition, according to claim 16, characterized in that it additionally comprises a thickener selected from the group consisting of magnesium aluminum silicate, hydroxyethyl acrylate/sodium acryloyldimethyltaurate copolymer, xanthan gum, silica, cetyl hydroxyethyl cellulose, and polyacrylate-13/polyisobutylene/polysorbate-20 blend and mixtures thereof.
    [0018]
    18. Topical composition, according to claim 17, characterized in that the thickener comprises hydroxyethyl acrylate/sodium acryloyldimethyltaurate copolymer.
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    同族专利:
    公开号 | 公开日
    AU2016206278A1|2017-02-09|
    JP2017025062A|2017-02-02|
    DK3120831T3|2021-10-11|
    US20170020799A1|2017-01-26|
    EP3120831A1|2017-01-25|
    JP6884522B2|2021-06-09|
    MX361590B|2018-12-11|
    EP3120831B1|2021-08-25|
    BR102016017090A2|2017-01-31|
    KR20170012086A|2017-02-02|
    CN106361592A|2017-02-01|
    AU2016206278B2|2021-08-19|
    US10130578B2|2018-11-20|
    RU2016129158A|2018-01-23|
    JP2021080278A|2021-05-27|
    RU2727807C2|2020-07-24|
    ES2892958T3|2022-02-07|
    CA2935367A1|2017-01-23|
    MX2016009666A|2017-05-01|
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    WO2021255260A1|2020-06-19|2021-12-23|L'oreal|Composition comprising a polyol and at least one polyglyceryl ester|
    FR3111546A1|2020-06-19|2021-12-24|L'oreal|Composition comprising a polyol, an ester of polyglycerol, a salt of hyaluronic acid and a specific hydrophilic polymer|
    WO2021255255A1|2020-06-19|2021-12-23|L'oreal|Composition comprising a polyol, a polyglycerol ester, a hyaluronic acid salt and a specific hydrophilic polymer|
    法律状态:
    2017-01-31| B03A| Publication of a patent application or of a certificate of addition of invention [chapter 3.1 patent gazette]|
    2019-10-29| B06U| Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette]|
    2021-06-22| B07A| Application suspended after technical examination (opinion) [chapter 7.1 patent gazette]|
    2021-11-16| B09A| Decision: intention to grant [chapter 9.1 patent gazette]|
    2022-01-18| B16A| Patent or certificate of addition of invention granted [chapter 16.1 patent gazette]|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 22/07/2016, OBSERVADAS AS CONDICOES LEGAIS. |
    优先权:
    申请号 | 申请日 | 专利标题
    US14/806,699|US10130578B2|2015-07-23|2015-07-23|Topical delivery of skin compositions having low pH|
    US14/806,699|2015-07-23|
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