WO2022124386A1 - Composition comprising ascorbic acid and cyclic amino acid - Google Patents
Composition comprising ascorbic acid and cyclic amino acid Download PDFInfo
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- WO2022124386A1 WO2022124386A1 PCT/JP2021/045429 JP2021045429W WO2022124386A1 WO 2022124386 A1 WO2022124386 A1 WO 2022124386A1 JP 2021045429 W JP2021045429 W JP 2021045429W WO 2022124386 A1 WO2022124386 A1 WO 2022124386A1
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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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
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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
- A61K8/67—Vitamins
- A61K8/676—Ascorbic acid, i.e. vitamin C
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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
Definitions
- the present invention relates to a composition comprising at least one of ascorbic acid and salts thereof and at least one cyclic amino acid, preferably a cosmetic composition comprising the same.
- Ascorbic acid is one of the key active ingredients in a cosmetic field. Since ascorbic acid has limited solubility in water, aqueous compositions including a high concentration of an ascorbic acid has been desired. So far, some prior art documents have reported technologies for obtaining compositions comprising a high concentration of ascorbic acid.
- JP-A-2018-138617 discloses an external composition comprising: (A) at least one member selected from the group consisting of ascorbic acid and salts of ascorbic acid; (B) at least one member selected from the group consisting of 3-O-ethylascorbic acid, salts of 3-O-ethylascorbic acid, and hydroxylated lecithin; and (C) polyethylene glycol.
- WO 2019/131892 discloses an external composition comprising: (A) at least one type of substance selected from the group consisting of an ascorbic acid and a salt of an ascorbic acid; (B) a diol having three carbon atoms; (C) at least one type of substance selected from the group consisting of low-molecular- weight betaines, salts of organic acids, salts of inorganic acids, basic amino acids, salts of the basic amino acids, a 3-0-ethyl ascorbic acid, and a salt of the 3-0-ethyl ascorbic acid; and (D) water, and having an ethoxy diglycol content of less than 30% by mass.
- US-B-7, 179,841 discloses a single-phase solution composition
- a single-phase solution composition comprising by weight: 5% to 40% L-ascorbic acid, 0.2% to 5.0% of a cinnamic acid derivative selected from p-coumaric acid, ferulic acid, caffeic acid, sinapinic acid, combinations thereof, and cis and trans isomers thereof; 10% to 60% of a solvent comprising a glycol ether and an alkanediol; and water; the composition having a pH of no more than about 3.5, and wherein when the cinnamic acid derivative is present in an amount greater than 0.5%, the composition further comprises a surfactant in an amount of 1.5% to 5.0%.
- An objective of the present invention is to provide compositions which are stable over time although they comprise an ascorbic acid or salts thereof in a high concentration.
- composition comprising: (a) at least one of ascorbic acid and salts thereof in an amount of 15% by weight or more relative to the total weight of the composition, and
- the (b) cyclic amino acid may comprise at least one aliphatic ring!
- the (b) cyclic amino acid may be selected from proline and proline derivatives.
- the weight ratio of the (a) ascorbic acid and salts thereof to the (b) cyclic amino acid(s) may be 1 to 100, preferably 1.5 to 75, and more preferable 2 to 50.
- composition according to the present invention may have a pH of 2.5 to 7.5.
- composition according to the present invention may be in the form of a single-phase solution.
- composition according to the present invention may further comprise water.
- the amount of the water in the composition may be 5% by weight or more, preferably 10% by weight or more, more preferably 15% by weight or more, and even more preferably 20% by weight or more, and may be 80% or less, preferably 70% by weight or less, more preferably 60% by weight or less, even more preferably 50% by weight or less, and in particular 40% by weight or less, relative to the total weight of the composition.
- composition according to the present invention may further comprise at least one hydrophilic organic solvent.
- the amount of the hydrophilic organic solvent(s) may be 1% by weight or more, preferably 5% by weight or more, more preferably 10% by weight or more, even more preferably 20% by weight or more, and in particular 30% by weight or more, and may be 70% by weight or less, preferably 60% by weight or less, and more preferably 50% by weight or less, relative to the total weight of the composition.
- composition according to the present invention may further comprise additional cosmetically active ingredients.
- the composition may comprise particulate materials in an amount of less than 5% by weight or less, preferably 3% by weight or less, more preferably 1% by weight or less, even more preferably 0.5% by weight or less, and in particular 0.1% by weight or less, relative to the total weight of the composition, or the composition may be free of any particulate materials.
- the composition may comprise surfactants in an amount of less than 5% by weight or less, preferably 3% by weight or less, more preferably 1% by weight or less, even more preferably 0.5% by weight or less, and in particular 0.1% by weight or less, relative to the total weight of the composition, or the composition may be free of any surfactants.
- the present invention also relates to a non-therapeutic cosmetic process for caring for and/or conditioning keratinous substances, such as skin, comprising: applying onto the keratinous substances a composition comprising:
- the present invention also relates to a use of (b) at least one cyclic amino acid in an amount of 1% by weight or more relative to a total weight of the composition to obtain a stable aqueous composition comprising (a) at least one of ascorbic acid and salts thereof in an amount of 15% by weight or more relative to the total weight of the composition.
- cyclic amino acids can improve the stability of aqueous compositions comprising a large amount of an ascorbic acid and/or salts thereof, thus completing the present invention.
- composition according to the present invention is a cosmetic composition comprising:
- the composition may be a cosmetic composition, preferably a cosmetic composition for a keratinous substance, and more preferably a cosmetic composition for caring for and/or conditioning a keratinous substance.
- the keratinous substance here means a material containing keratin as a main constituent element, and examples thereof include the skin, scalp, lips, and the like.
- the form of the composition according to the present invention is not particularly limited.
- the composition according to the present invention is liquid at room temperature (25°C) and atmospheric pressure (10 5 Pa).
- the composition may take various forms, such as a solution, an aqueous solution, a lotion, a milky lotion, a cream, a gel, a liquid gel, a paste, a serum, a suspension, a dispersion, a fluid, a milk, an emulsion (O/W or W/O form), or the like.
- the composition according to the present invention be in the form of an aqueous solution, and in particular a single-phase aqueous solution.
- the term “single-phase aqueous solution” here means a solution having one homogeneous aqueous phase.
- the composition according to the present invention may preferably be used as a cosmetic composition, in particular a leave-on type cosmetic composition.
- the composition according to the present invention may be intended for application onto a keratinous substance, preferably skin, for example, facial skin.
- the composition according to the present invention has a cosmetic effect, in particular as anti-aging, whitening, and/or anti-wrinkle efficacy on keratinous substances, in particular skin thanks to the (a) ascorbic acid or salts thereof in a high concentration.
- composition according to the present invention may be transparent or translucent, preferably transparent.
- the composition according to the present invention comprises (a) at least one of ascorbic acid and salts thereof and (b) at least one cyclic amino acid.
- the ingredients in the composition will be described in a detailed manner below.
- composition according to the present invention comprises (a) at least one ascorbic acid or a salt thereof.
- a single type of the ascorbic acid and salts thereof may be used, but two or more different types of the ascorbic acid and salts thereof may be used in combination.
- Ascorbic acid which is also known as Vitamin C, is known as a cosmetically active ingredient. Ascorbic acids are used as anti-aging, whitening, and/or anti-wrinkle ingredients on keratinous substances, in particular skin, since they have functions of stimulating collagen synthesis and reducing melanin. Ascorbic acid in general means L-ascorbic acid.
- the salt of ascorbic acid is preferably a pharmaceutically acceptable salt.
- the salts of ascorbic acid include, but are not limited to, salts with an organic base (for example, salts with a tertiary amine such as trimethylamine salts, triethylamine salts, monoethanolamine salts, triethanolamine salts and pyridine salts, basic ammonium salts such as arginine, and the like), salts with an inorganic base (for example, alkali metal salts such as ammonium salts, sodium salts and potassium salts, alkaline earth metal salts such as calcium salts and magnesium salts, aluminum salts, and the like) and the like.
- an organic base for example, salts with a tertiary amine such as trimethylamine salts, triethylamine salts, monoethanolamine salts, triethanolamine salts and pyridine salts, basic ammonium salts such as arginine, and the like
- salts with an inorganic base for
- the (a) ascorbic acid and/or salts thereof is present in an amount of 15% by weight or more relative to the total weight of the composition according to the present invention. It is preferred that the (a) ascorbic acid and/or salts thereof be present in an amount of 17.5% by weight or more, more preferably 20% by weight or more, even more preferably 22.5% by weight or more, and in particular 25% by weight or more, and be present in an amount of 60% by weight or less, preferably 55% by weight or less, more preferably 50% by weight or less, and in particular 45% by weight or less, relative to the total weight of the composition.
- composition according to the present invention comprises (b) at least one cyclic amino acid.
- a single type of cyclic amino acid may be used, but two or more different types of cyclic amino acids may be used in combination.
- cyclic amino acid herein means amino acids having at least one cyclic structure.
- examples of cyclic amino acids include, but are not limited to, proline, proline derivatives, such as hydroxyproline, in particular 4-hydroxyproline, and methylproline, in particular N-methylproline, phenylalanine, tyrosine, tryptophan, and derivatives thereof.
- the cyclic structure of the cyclic amino acid comprises at least one aliphatic ring. In another preferred embodiment of the present invention, the cyclic structure of the cyclic amino acid does not comprise an aromatic ring. Therefore, preferably, the cyclic structure of the cyclic amino acid is an aliphatic ring.
- the (b) cyclic amino acid is selected from proline and proline derivatives, such as hydroxyproline and methylproline, and combinations thereof. These compounds are very preferable for the present invention since it is known that they possess a conditioning effect on keratinous substances, for example, an anti-aging efficacy and anti-wrinkle efficacy.
- the (b) cyclic amino acid(s) is(are) present in an amount of 1% by weight or more relative to the total weight of the composition. It is preferred that the (b) cyclic amino acid(s) be present in an amount of 2% by weight or more, more preferably 3% by weight or more, even more preferably 4% by weight or more, and in particular 5% by weight or more, and be present in an amount of 30% by weight or less, preferably 25% by weight or less, more preferably 20% by weight or less, and in particular 15% by weight or less, relative to the total weight of the composition.
- the weight ratio of the (a) ascorbic acid and salts thereof to the (b) cyclic amino acid(s) in the composition can be 1 or more, preferably 1.5 or more, more preferably 1.75 or more, and in particular 2 or more.
- the weight ratio of the (a) ascorbic acid and salts thereof to the (b) cyclic amino acid(s) in the composition is 100 or less, preferably 75 or less, and more preferably 50 or less.
- composition according to the present invention may comprise at least one cosmetically acceptable hydrophilic organic solvent.
- hydrophilic here means substances having a solubility of at least 1 g/L, preferably at least 10 g/L, and more preferably at least 100 g/L, in water at room temperature (25°C) and atmospheric pressure (10 5 Pa).
- the cosmetically acceptable hydrophilic organic solvent(s) may include, for example, substantially linear or branched lower mono-alcohols having from 1 to 8 carbon atoms, such as ethanol, propanol, butanol, isopropanol, and isobutanol; aromatic alcohols, such as benzyl alcohol and phenylethyl alcohol; polyols or polyol ethers, such as propylene glycol, dipropylene glycol, isoprene glycol, butylene glycol, glycerine, propanediol, caprylyl glycol, sorbitol, ethylene glycol monomethyl, monoethyl and monobutyl ethers, propylene glycol ethers, such as propylene glycol monomethylether, diethylene glycol alkyl ethers, such as diethylene glycol monoethylether or monobutylether; polyethylene glycols, such as PEG-4, PEG-6, and PEG-8, and their derivatives
- the amount of the cosmetically acceptable hydrophilic organic solvent(s) in the composition according to the present invention may be from 1% by weight or more, preferably 5% by weight or more, more preferably 10% by weight or more, even more preferably 20% by weight or more, and in particular 30% by weight or more, and may be 70% by weight or less, preferably 60% by weight or less, and more preferably 50% by weight or less, relative to the total weight of the composition.
- the composition comprises the cosmetically acceptable hydrophilic organic solvent(s) in an amount larger than that of water.
- the pH of the composition according to the present invention may be adjusted to the desired value using at least one pH adjusting agent, such as an acidifying or a basifying agent, for example, which are commonly used in cosmetic products.
- the pH of the composition according to the present invention may be 9.0 or less, preferably 8.5 or less, more preferably 8.0 or less, even more preferably 7.5 or less, and in particular 7.0 or less, and may be 2.5 or more, preferably 3.0 or more, and more preferably 3.5 or more at 25°C.
- acidifying agents mention may be made, by way of example, of mineral or organic acids such as hydrochloric acid, ortho-phosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, and lactic acid, and sulfonic acids.
- mineral or organic acids such as hydrochloric acid, ortho-phosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, and lactic acid, and sulfonic acids.
- basifying agents mention may be made, by way of example, of hydroxides of an alkali metal or an alkaline-earth metal, for instance sodium hydroxide or potassium hydroxide; quaternary ammonium hydroxides and guanidinium hydroxide; alkali metal silicates, such as sodium metasilicates; carbonates and bicarbonates, particularly of a primary amine, secondary amine or tertiary amine, of an alkali metal or alkaline-earth metal, or of ammonium; and the compounds of the following formula:
- W is a Ci-Ce alkylene residue optionally substituted with a hydroxyl group or a Ci-Ce alkyl group;
- Rx, Ry, Rz and Rt which may be identical or different, represent a hydrogen atom or a Ci-Ce alkyl, Ci-C 6 hydroxyalkyl or Ci-Ce aminoalkyl group. Mention may especially be made of 1,3-diaminopropane, l,3-diamino-2 -propanol, spermine and spermidine.
- the pH adjusting agent(s) may be used in an amount ranging from 0.001% to 10% by weight, preferably from 0.01% to 5% by weight, and more preferably from 0.1% to 3% by weight, relative to the total weight of the composition.
- composition according to the present invention may comprise at least one additional cosmetically active ingredient other than the components (a) and (b) above.
- active ingredient used herein means an organic compound having any cosmetic or dermatological effects on a keratinous substance, such as skin.
- Well-known cosmetic active ingredients in the cosmetic field can be used as the optional active ingredients.
- the additional cosmetic ingredients are active ingredients for caring for or conditioning keratinous substances, such as skin.
- the active ingredients are for improving a condition of keratinous substances, such as skin.
- the additional active ingredients may include, but are not limited to, derivatives of vitamins, such as derivatives of vitamin A (retinol), vitamin C (ascorbic acid), vitamin B3 (niacin) and the like, mucopolysaccharides and derivatives thereof, such as hyaluronic acid and chondroitin and derivatives thereof.
- vitamins such as derivatives of vitamin A (retinol), vitamin C (ascorbic acid), vitamin B3 (niacin) and the like, mucopolysaccharides and derivatives thereof, such as hyaluronic acid and chondroitin and derivatives thereof.
- the derivative of the ascorbic acid mention may be made of, for example, 5,6-di-O-dimethylsilyl ascorbate, which is commercially available as PRO-AA from Exsymol SAM; dl-alpha-tocopheryl-2-l-ascorbyl phosphate which is commercially available as SEPIVITAL EPC from Senju Pharmaceutical Co., Ltd.; sodium ascorbyl phosphate which is commercially available as Stay-C 50 from Roche; ascorbyl glucoside which is commercially available from Hayashibara Biochemical Labs., Inc.; 3-O-ethyl ascorbic acid; and the like.
- the amount of the additional active ingredient(s) in the composition according to the present invention may be from 0.01% by weight or more, preferably 0.05% by weight or more, more preferably 0.1 % by weight or more, and even more preferably 1 % by weight or more, and may be 30% by weight or less, preferably 20% by weight or less, more preferably 10% by weight or less, and even more preferably 5% by weight or less, relative to the total weight of the composition.
- composition according to the present invention preferably includes water.
- the amount of water in the composition according to the present invention may be 5% by weight or more, preferably 10% by weight or more, more preferably 15% by weight or more, and even more preferably 20% by weight or more, and may be 80% or less, preferably 70% by weight or less, more preferably 60% by weight or less, even more preferably 50% by weight or less, and in particular 40% by weight or less, relative to the total weight of the composition.
- composition according to the present invention may also comprise any adjuvant(s) usually used in the field of cosmetics, chosen, for example, from anionic, cationic, nonionic or amphoteric polymers, anionic, cationic, nonionic or amphoteric surfactants, oils, hydrophobic organic solvents, gums, resins, thickeners, dispersants, antioxidants, buffers, organic or inorganic fillers, preserving agents, such as phenoxyethanol, co-preservatives, opacifying agents, fragrances, neutralizers, antiseptics, UV-screening agents, chelating agents, such as trisodium ethylenediamine disuccinate, dispersing agents, dyes and/or pigments, emollients or collagen-protecting agents, and mixtures thereof.
- adjuvant(s) usually used in the field of cosmetics chosen, for example, from anionic, cationic, nonionic or amphoteric polymers, anionic, cationic, nonionic or amphoteric sur
- the adjuvants may be present in the composition of the present invention in an amount ranging from 0.01% to 30% by weight, preferably from 0.1% to 20% by weight, and more preferably from 0.5% to 10% by weight, relative to the total weight of the composition.
- the composition according to the present invention is in the form of a single-phase aqueous solution. Therefore, the composition preferably includes an oil in an amount of less than 5% by weight or less, preferably 3% by weight or less, more preferably 1% by weight or less, even more preferably 0.5% by weight or less, and in particular 0.1% by weight or less, relative to the total weight of the composition. In another preferred embodiment of the present invention, the composition is free of any oils.
- the composition preferably includes particulate materials, such as fillers, in an amount of less than 5% by weight or less, preferably 3% by weight or less, more preferably 1% by weight or less, even more preferably 0.5% by weight or less, and in particular 0.1 % by weight or less, relative to the total weight of the composition,.
- the composition is free of any particulate materials.
- the composition preferably includes surfactants in an amount of less than 5% by weight or less, preferably 3% by weight or less, more preferably 1% by weight or less, even more preferably 0.5% by weight or less, and in particular 0.1 % by weight or less, relative to the total weight of the composition,.
- the composition is free of any surfactants.
- the composition according to the present invention can be prepared by mixing the above-described essential and optional ingredients in a conventional manner. In order to ensure that the (a) ascorbic acid or salts thereof is completely dissolved, it is preferable to heat the composition to about 40 to 80°C until it is dissolved. It is possible to further comprise mixing any of the optional ingredients and heating the composition until an ingredient is dissolved.
- the present invention also relates to a non-therapeutic method or process, preferably a cosmetic method or process, and more preferably a cosmetic method or process for caring for and/or conditioning keratinous substances, such as skin, scalp, lips, in particular facial skin, comprising: applying onto the keratinous substance a composition comprising:
- the present invention also relates to a use of the cyclic amino acids to make the (a) at least one of ascorbic acid and salts thereof stable in water.
- the present invention also relates to a use of the (b) at least one cyclic amino acid in an amount of 1% by weight or more relative to the total weight of the composition, to make the (a) at least one of ascorbic acid and salts thereof in an amount of 15% by weight or more relative to the total weight of the composition stable in water.
- the present invention also relates to a use of the (b) at least one cyclic amino acid in an amount of 1% by weight or more relative to the total weight of the composition to obtain a stable aqueous composition comprising the (a) at least one of ascorbic acid and salts thereof in an amount of 15% by weight or more relative to the total weight of the composition.
- compositions, (a) ascorbic acid and salts thereof, and the (b) cyclic amino acid in the composition according to the present invention above can be applied to the composition, ascorbic acid and salts thereof, and the (b) cyclic amino acid for the method, process, and use according to the present inventions.
- the composition used in the process, method, and use according to the present invention may include any of the optional ingredients as explained above for the composition according to the present invention.
- Homogeneous solution compositions according to the Examples and Comparative Examples were prepared by mixing the ingredients as listed in Tables 1 to 4 with a magnetic stirrer. The compositions were heated to about 60°C in order to dissolve the ascorbic acid and then cooled down to room temperature (RT). The numerical values for the amounts of the ingredients shown in Table 1 are all based on “% by weight” as active raw materials. The obtained compositions according to all of the examples were transparent. [Evaluation]
- compositions according to the Examples and Comparative Examples were filled into a glass jar, and each of the glass jars was held under temperature conditions of -5°C, 4°C, or RT (25°C) for 1 , 2, 4, or 8 weeks as shown in the tables. Each glass jar was then observed visually and evaluated under the following criteria.
- compositions according to the Examples which include the specific combination of the (a) ascorbic acid and the (b) cyclic amino acid of the present invention, showed excellent stability for a long time, without generating any crystals of ascorbic acid.
- compositions according to the Comparative Examples which do not include the specific combination of the present invention, showed inferior stability and generated crystals of ascorbic acid.
- compositions according to the present invention are very suitable as cosmetic compositions for caring for and/or conditioning keratinous substances, such as skin, since they can provide cosmetic effects on keratinous substances produced from a high concentration of ascorbic acid.
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Abstract
The present invention relates to a cosmetic composition comprising: (a) at least one of ascorbic acid and salts thereof in an amount of 15% by weight or more relative to the total weight of the composition; and (b) at least one cyclic amino acid in an amount of 1% by weight or more relative to the total weight of the composition.
Description
DESCRIPTION
TITLE OF INVENTION
COMPOSITION COMPRISING ASCORBIC ACID AND CYCLIC AMINO ACID
TECHNICAL FIELD
The present invention relates to a composition comprising at least one of ascorbic acid and salts thereof and at least one cyclic amino acid, preferably a cosmetic composition comprising the same.
BACKGROUND ART
Ascorbic acid is one of the key active ingredients in a cosmetic field. Since ascorbic acid has limited solubility in water, aqueous compositions including a high concentration of an ascorbic acid has been desired. So far, some prior art documents have reported technologies for obtaining compositions comprising a high concentration of ascorbic acid.
For example, JP-A-2018-138617 discloses an external composition comprising: (A) at least one member selected from the group consisting of ascorbic acid and salts of ascorbic acid; (B) at least one member selected from the group consisting of 3-O-ethylascorbic acid, salts of 3-O-ethylascorbic acid, and hydroxylated lecithin; and (C) polyethylene glycol.
Also, WO 2019/131892 discloses an external composition comprising: (A) at least one type of substance selected from the group consisting of an ascorbic acid and a salt of an ascorbic acid; (B) a diol having three carbon atoms; (C) at least one type of substance selected from the group consisting of low-molecular- weight betaines, salts of organic acids, salts of inorganic acids, basic amino acids, salts of the basic amino acids, a 3-0-ethyl ascorbic acid, and a salt of the 3-0-ethyl ascorbic acid; and (D) water, and having an ethoxy diglycol content of less than 30% by mass.
Also, US-B-7, 179,841 discloses a single-phase solution composition comprising by weight: 5% to 40% L-ascorbic acid, 0.2% to 5.0% of a cinnamic acid derivative selected from p-coumaric acid, ferulic acid, caffeic acid, sinapinic acid, combinations thereof, and cis and trans isomers thereof; 10% to 60% of a solvent comprising a glycol ether and an alkanediol; and water; the composition having a pH of no more than about 3.5, and wherein when the cinnamic acid derivative is present in an amount greater than 0.5%, the composition further comprises a surfactant in an amount of 1.5% to 5.0%.
However, there is still a need to develop compositions including an ascorbic acid in a high concentration while being stable for a long time without causing the problem of crystallization of the ascorbic acid.
DISCLOSURE OF INVENTION
An objective of the present invention is to provide compositions which are stable over time although they comprise an ascorbic acid or salts thereof in a high concentration.
The above objective of the present invention can be achieved by a composition comprising: (a) at least one of ascorbic acid and salts thereof in an amount of 15% by weight or more
relative to the total weight of the composition, and
(b) at least one cyclic amino acid in an amount of 1% by weight or more relative to the total weight of the composition.
The (b) cyclic amino acid may comprise at least one aliphatic ring!
The (b) cyclic amino acid may be selected from proline and proline derivatives.
The weight ratio of the (a) ascorbic acid and salts thereof to the (b) cyclic amino acid(s) may be 1 to 100, preferably 1.5 to 75, and more preferable 2 to 50.
The composition according to the present invention may have a pH of 2.5 to 7.5.
The composition according to the present invention may be in the form of a single-phase solution.
The composition according to the present invention may further comprise water.
The amount of the water in the composition may be 5% by weight or more, preferably 10% by weight or more, more preferably 15% by weight or more, and even more preferably 20% by weight or more, and may be 80% or less, preferably 70% by weight or less, more preferably 60% by weight or less, even more preferably 50% by weight or less, and in particular 40% by weight or less, relative to the total weight of the composition.
The composition according to the present invention may further comprise at least one hydrophilic organic solvent.
The amount of the hydrophilic organic solvent(s) may be 1% by weight or more, preferably 5% by weight or more, more preferably 10% by weight or more, even more preferably 20% by weight or more, and in particular 30% by weight or more, and may be 70% by weight or less, preferably 60% by weight or less, and more preferably 50% by weight or less, relative to the total weight of the composition.
The composition according to the present invention may further comprise additional cosmetically active ingredients.
The composition may comprise particulate materials in an amount of less than 5% by weight or less, preferably 3% by weight or less, more preferably 1% by weight or less, even more preferably 0.5% by weight or less, and in particular 0.1% by weight or less, relative to the total weight of the composition, or the composition may be free of any particulate materials.
The composition may comprise surfactants in an amount of less than 5% by weight or less, preferably 3% by weight or less, more preferably 1% by weight or less, even more preferably 0.5% by weight or less, and in particular 0.1% by weight or less, relative to the total weight of the composition, or the composition may be free of any surfactants.
The present invention also relates to a non-therapeutic cosmetic process for caring for and/or conditioning keratinous substances, such as skin, comprising: applying onto the keratinous substances a composition comprising:
(a) at least one of ascorbic acid and salts thereof in an amount of 15% by weight or more relative to the total weight of the composition; and
(b) at least one cyclic amino acid in an amount of 1 % by weight or more relative to the total weight of the composition.
The present invention also relates to a use of (b) at least one cyclic amino acid in an amount of 1% by weight or more relative to a total weight of the composition to obtain a stable aqueous composition comprising (a) at least one of ascorbic acid and salts thereof in an amount of 15% by weight or more relative to the total weight of the composition.
BEST MODE FOR CARRYING OUT THE INVENTION
After diligent research, the inventors have surprisingly discovered that cyclic amino acids can improve the stability of aqueous compositions comprising a large amount of an ascorbic acid and/or salts thereof, thus completing the present invention.
Thus, the composition according to the present invention is a cosmetic composition comprising:
(a) at least one of ascorbic acid and salts thereof in an amount of 15% by weight or more relative to the total weight of the composition, and
(b) at least one cyclic amino acid in an amount of 1% by weight or more relative to the total weight of the composition.
Hereinafter, the composition, process, and use according to the present invention will be explained in a more detailed manner.
[Composition]
The composition may be a cosmetic composition, preferably a cosmetic composition for a keratinous substance, and more preferably a cosmetic composition for caring for and/or conditioning a keratinous substance. The keratinous substance here means a material containing keratin as a main constituent element, and examples thereof include the skin, scalp, lips, and the like.
The form of the composition according to the present invention is not particularly limited. In general, the composition according to the present invention is liquid at room temperature (25°C) and atmospheric pressure (105 Pa). The composition may take various forms, such as a solution, an aqueous solution, a lotion, a milky lotion, a cream, a gel, a liquid gel, a paste, a serum, a suspension, a dispersion, a fluid, a milk, an emulsion (O/W or W/O form), or the like. It is preferable that the composition according to the present invention be in the form of an aqueous solution, and in particular a single-phase aqueous solution. The term “single-phase aqueous solution” here means a solution having one homogeneous aqueous phase.
The composition according to the present invention may preferably be used as a cosmetic composition, in particular a leave-on type cosmetic composition. The composition according to the present invention may be intended for application onto a keratinous substance, preferably skin, for example, facial skin. The composition according to the present invention has a cosmetic effect, in particular as anti-aging, whitening, and/or anti-wrinkle efficacy on keratinous substances, in particular skin thanks to the (a) ascorbic acid or salts thereof in a high concentration.
The composition according to the present invention may be transparent or translucent, preferably transparent.
The composition according to the present invention comprises (a) at least one of ascorbic acid and salts thereof and (b) at least one cyclic amino acid. The ingredients in the composition will be described in a detailed manner below.
(Ascorbic Acid)
The composition according to the present invention comprises (a) at least one ascorbic acid or a salt thereof. A single type of the ascorbic acid and salts thereof may be used, but two or more different types of the ascorbic acid and salts thereof may be used in combination.
Ascorbic acid, which is also known as Vitamin C, is known as a cosmetically active ingredient. Ascorbic acids are used as anti-aging, whitening, and/or anti-wrinkle ingredients on keratinous substances, in particular skin, since they have functions of stimulating collagen synthesis and reducing melanin. Ascorbic acid in general means L-ascorbic acid.
The salt of ascorbic acid is preferably a pharmaceutically acceptable salt. The salts of ascorbic acid include, but are not limited to, salts with an organic base (for example, salts with a tertiary amine such as trimethylamine salts, triethylamine salts, monoethanolamine salts, triethanolamine salts and pyridine salts, basic ammonium salts such as arginine, and the like), salts with an inorganic base (for example, alkali metal salts such as ammonium salts, sodium salts and potassium salts, alkaline earth metal salts such as calcium salts and magnesium salts, aluminum salts, and the like) and the like.
The (a) ascorbic acid and/or salts thereof is present in an amount of 15% by weight or more relative to the total weight of the composition according to the present invention. It is preferred that the (a) ascorbic acid and/or salts thereof be present in an amount of 17.5% by weight or more, more preferably 20% by weight or more, even more preferably 22.5% by weight or more, and in particular 25% by weight or more, and be present in an amount of 60% by weight or less, preferably 55% by weight or less, more preferably 50% by weight or less, and in particular 45% by weight or less, relative to the total weight of the composition.
(Cyclic Amino Acid)
The composition according to the present invention comprises (b) at least one cyclic amino acid. A single type of cyclic amino acid may be used, but two or more different types of cyclic amino acids may be used in combination.
The term “cyclic amino acid” herein means amino acids having at least one cyclic structure. Examples of cyclic amino acids include, but are not limited to, proline, proline derivatives, such as hydroxyproline, in particular 4-hydroxyproline, and methylproline, in particular N-methylproline, phenylalanine, tyrosine, tryptophan, and derivatives thereof.
In one preferred embodiment of the present invention, the cyclic structure of the cyclic amino acid comprises at least one aliphatic ring. In another preferred embodiment of the present invention, the cyclic structure of the cyclic amino acid does not comprise an aromatic ring. Therefore, preferably, the cyclic structure of the cyclic amino acid is an aliphatic ring.
In the most preferred embodiment of the present invention, the (b) cyclic amino acid is selected from proline and proline derivatives, such as hydroxyproline and methylproline, and combinations thereof. These compounds are very preferable for the present invention since it is known that
they possess a conditioning effect on keratinous substances, for example, an anti-aging efficacy and anti-wrinkle efficacy.
The (b) cyclic amino acid(s) is(are) present in an amount of 1% by weight or more relative to the total weight of the composition. It is preferred that the (b) cyclic amino acid(s) be present in an amount of 2% by weight or more, more preferably 3% by weight or more, even more preferably 4% by weight or more, and in particular 5% by weight or more, and be present in an amount of 30% by weight or less, preferably 25% by weight or less, more preferably 20% by weight or less, and in particular 15% by weight or less, relative to the total weight of the composition.
According to one preferred embodiment of the present invention, the weight ratio of the (a) ascorbic acid and salts thereof to the (b) cyclic amino acid(s) in the composition can be 1 or more, preferably 1.5 or more, more preferably 1.75 or more, and in particular 2 or more. In general, the weight ratio of the (a) ascorbic acid and salts thereof to the (b) cyclic amino acid(s) in the composition is 100 or less, preferably 75 or less, and more preferably 50 or less.
(Hydrophilic Organic Solvent)
The composition according to the present invention may comprise at least one cosmetically acceptable hydrophilic organic solvent. The term “hydrophilic” here means substances having a solubility of at least 1 g/L, preferably at least 10 g/L, and more preferably at least 100 g/L, in water at room temperature (25°C) and atmospheric pressure (105 Pa). The cosmetically acceptable hydrophilic organic solvent(s) may include, for example, substantially linear or branched lower mono-alcohols having from 1 to 8 carbon atoms, such as ethanol, propanol, butanol, isopropanol, and isobutanol; aromatic alcohols, such as benzyl alcohol and phenylethyl alcohol; polyols or polyol ethers, such as propylene glycol, dipropylene glycol, isoprene glycol, butylene glycol, glycerine, propanediol, caprylyl glycol, sorbitol, ethylene glycol monomethyl, monoethyl and monobutyl ethers, propylene glycol ethers, such as propylene glycol monomethylether, diethylene glycol alkyl ethers, such as diethylene glycol monoethylether or monobutylether; polyethylene glycols, such as PEG-4, PEG-6, and PEG-8, and their derivatives, and a combination thereof.
The amount of the cosmetically acceptable hydrophilic organic solvent(s) in the composition according to the present invention may be from 1% by weight or more, preferably 5% by weight or more, more preferably 10% by weight or more, even more preferably 20% by weight or more, and in particular 30% by weight or more, and may be 70% by weight or less, preferably 60% by weight or less, and more preferably 50% by weight or less, relative to the total weight of the composition.
In one specific embodiment of the present invention, the composition comprises the cosmetically acceptable hydrophilic organic solvent(s) in an amount larger than that of water.
(pH Adjusting Agent)
The pH of the composition according to the present invention may be adjusted to the desired value using at least one pH adjusting agent, such as an acidifying or a basifying agent, for example, which are commonly used in cosmetic products.
The pH of the composition according to the present invention may be 9.0 or less, preferably 8.5 or less, more preferably 8.0 or less, even more preferably 7.5 or less, and in particular 7.0 or less, and may be 2.5 or more, preferably 3.0 or more, and more preferably 3.5 or more at 25°C.
Among the acidifying agents, mention may be made, by way of example, of mineral or organic acids such as hydrochloric acid, ortho-phosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, and lactic acid, and sulfonic acids.
Among the basifying agents, mention may be made, by way of example, of hydroxides of an alkali metal or an alkaline-earth metal, for instance sodium hydroxide or potassium hydroxide; quaternary ammonium hydroxides and guanidinium hydroxide; alkali metal silicates, such as sodium metasilicates; carbonates and bicarbonates, particularly of a primary amine, secondary amine or tertiary amine, of an alkali metal or alkaline-earth metal, or of ammonium; and the compounds of the following formula:
RX \ z RZ
XN W N Ry Rt in which
W is a Ci-Ce alkylene residue optionally substituted with a hydroxyl group or a Ci-Ce alkyl group; Rx, Ry, Rz and Rt, which may be identical or different, represent a hydrogen atom or a Ci-Ce alkyl, Ci-C6 hydroxyalkyl or Ci-Ce aminoalkyl group. Mention may especially be made of 1,3-diaminopropane, l,3-diamino-2 -propanol, spermine and spermidine.
The pH adjusting agent(s) may be used in an amount ranging from 0.001% to 10% by weight, preferably from 0.01% to 5% by weight, and more preferably from 0.1% to 3% by weight, relative to the total weight of the composition.
(Additional Active Ingredient)
The composition according to the present invention may comprise at least one additional cosmetically active ingredient other than the components (a) and (b) above. The term “active ingredient” used herein means an organic compound having any cosmetic or dermatological effects on a keratinous substance, such as skin. Well-known cosmetic active ingredients in the cosmetic field can be used as the optional active ingredients. Preferably, the additional cosmetic ingredients are active ingredients for caring for or conditioning keratinous substances, such as skin. For example, the active ingredients are for improving a condition of keratinous substances, such as skin.
The additional active ingredients may include, but are not limited to, derivatives of vitamins, such as derivatives of vitamin A (retinol), vitamin C (ascorbic acid), vitamin B3 (niacin) and the like, mucopolysaccharides and derivatives thereof, such as hyaluronic acid and chondroitin and derivatives thereof. As the derivative of the ascorbic acid, mention may be made of, for example, 5,6-di-O-dimethylsilyl ascorbate, which is commercially available as PRO-AA from Exsymol SAM; dl-alpha-tocopheryl-2-l-ascorbyl phosphate which is commercially available as SEPIVITAL EPC from Senju Pharmaceutical Co., Ltd.; sodium ascorbyl phosphate which is commercially available as Stay-C 50 from Roche; ascorbyl glucoside which is commercially available from Hayashibara Biochemical Labs., Inc.; 3-O-ethyl ascorbic acid; and the like.
The amount of the additional active ingredient(s) in the composition according to the present invention may be from 0.01% by weight or more, preferably 0.05% by weight or more, more preferably 0.1 % by weight or more, and even more preferably 1 % by weight or more, and may be 30% by weight or less, preferably 20% by weight or less, more preferably 10% by weight or less, and even more preferably 5% by weight or less, relative to the total weight of the composition.
(Water)
The composition according to the present invention preferably includes water.
The amount of water in the composition according to the present invention may be 5% by weight or more, preferably 10% by weight or more, more preferably 15% by weight or more, and even more preferably 20% by weight or more, and may be 80% or less, preferably 70% by weight or less, more preferably 60% by weight or less, even more preferably 50% by weight or less, and in particular 40% by weight or less, relative to the total weight of the composition.
(Adjuvants)
The composition according to the present invention may also comprise any adjuvant(s) usually used in the field of cosmetics, chosen, for example, from anionic, cationic, nonionic or amphoteric polymers, anionic, cationic, nonionic or amphoteric surfactants, oils, hydrophobic organic solvents, gums, resins, thickeners, dispersants, antioxidants, buffers, organic or inorganic fillers, preserving agents, such as phenoxyethanol, co-preservatives, opacifying agents, fragrances, neutralizers, antiseptics, UV-screening agents, chelating agents, such as trisodium ethylenediamine disuccinate, dispersing agents, dyes and/or pigments, emollients or collagen-protecting agents, and mixtures thereof.
The adjuvants may be present in the composition of the present invention in an amount ranging from 0.01% to 30% by weight, preferably from 0.1% to 20% by weight, and more preferably from 0.5% to 10% by weight, relative to the total weight of the composition.
In one preferred embodiment of the present invention, the composition according to the present invention is in the form of a single-phase aqueous solution. Therefore, the composition preferably includes an oil in an amount of less than 5% by weight or less, preferably 3% by weight or less, more preferably 1% by weight or less, even more preferably 0.5% by weight or less, and in particular 0.1% by weight or less, relative to the total weight of the composition. In another preferred embodiment of the present invention, the composition is free of any oils.
In another preferred embodiment of the present invention, the composition preferably includes particulate materials, such as fillers, in an amount of less than 5% by weight or less, preferably 3% by weight or less, more preferably 1% by weight or less, even more preferably 0.5% by weight or less, and in particular 0.1 % by weight or less, relative to the total weight of the composition,. In another preferred embodiment of the present invention, the composition is free of any particulate materials.
In another preferred embodiment of the present invention, the composition preferably includes surfactants in an amount of less than 5% by weight or less, preferably 3% by weight or less, more preferably 1% by weight or less, even more preferably 0.5% by weight or less, and in particular 0.1 % by weight or less, relative to the total weight of the composition,. In another preferred embodiment of the present invention, the composition is free of any surfactants.
The composition according to the present invention can be prepared by mixing the above-described essential and optional ingredients in a conventional manner. In order to ensure that the (a) ascorbic acid or salts thereof is completely dissolved, it is preferable to heat the composition to about 40 to 80°C until it is dissolved. It is possible to further comprise mixing any of the optional ingredients and heating the composition until an ingredient is dissolved.
[Cosmetic Process and Use]
The present invention also relates to a non-therapeutic method or process, preferably a cosmetic method or process, and more preferably a cosmetic method or process for caring for and/or conditioning keratinous substances, such as skin, scalp, lips, in particular facial skin, comprising: applying onto the keratinous substance a composition comprising:
(a) at least one of ascorbic acid and salts thereof in an amount of 15% by weight or more relative to the total weight of the composition; and
(b) at least one cyclic amino acid in an amount of 1 % by weight or more relative to the total weight of the composition.
The present invention also relates to a use of the cyclic amino acids to make the (a) at least one of ascorbic acid and salts thereof stable in water. In particular, the present invention also relates to a use of the (b) at least one cyclic amino acid in an amount of 1% by weight or more relative to the total weight of the composition, to make the (a) at least one of ascorbic acid and salts thereof in an amount of 15% by weight or more relative to the total weight of the composition stable in water.
The present invention also relates to a use of the (b) at least one cyclic amino acid in an amount of 1% by weight or more relative to the total weight of the composition to obtain a stable aqueous composition comprising the (a) at least one of ascorbic acid and salts thereof in an amount of 15% by weight or more relative to the total weight of the composition.
The same explanations for the composition, (a) ascorbic acid and salts thereof, and the (b) cyclic amino acid in the composition according to the present invention above can be applied to the composition, ascorbic acid and salts thereof, and the (b) cyclic amino acid for the method, process, and use according to the present inventions. The composition used in the process, method, and use according to the present invention may include any of the optional ingredients as explained above for the composition according to the present invention.
EXAMPLES
The present invention will be described in more detail by way of examples which however should not be construed as limiting the scope of the present invention.
[Compositions]
Homogeneous solution compositions according to the Examples and Comparative Examples were prepared by mixing the ingredients as listed in Tables 1 to 4 with a magnetic stirrer. The compositions were heated to about 60°C in order to dissolve the ascorbic acid and then cooled down to room temperature (RT). The numerical values for the amounts of the ingredients shown in Table 1 are all based on “% by weight” as active raw materials. The obtained compositions according to all of the examples were transparent.
[Evaluation]
Each of the compositions according to the Examples and Comparative Examples was filled into a glass jar, and each of the glass jars was held under temperature conditions of -5°C, 4°C, or RT (25°C) for 1 , 2, 4, or 8 weeks as shown in the tables. Each glass jar was then observed visually and evaluated under the following criteria.
5: No crystals were observed.
3: Crystals were observed. 1 : Crystals ere observed very clearly.
The results are shown in Tables 1 to 4.
Table 1
Table 3
Table 4
As can be seen from Tables 1 to 4, the compositions according to the Examples, which include the specific combination of the (a) ascorbic acid and the (b) cyclic amino acid of the present invention, showed excellent stability for a long time, without generating any crystals of ascorbic acid. On the other hand, the compositions according to the Comparative Examples, which do not include the specific combination of the present invention, showed inferior stability and generated crystals of ascorbic acid.
Accordingly, it can be concluded that the compositions according to the present invention are very suitable as cosmetic compositions for caring for and/or conditioning keratinous substances, such as skin, since they can provide cosmetic effects on keratinous substances produced from a high concentration of ascorbic acid.
Claims
1. A cosmetic composition comprising:
(a) at least one of ascorbic acid and salts thereof in an amount of 15% by weight or more relative to the total weight of the composition; and
(b) at least one cyclic amino acid in an amount of 1% by weight or more relative to the total weight of the composition.
2. The composition according to Claim 1 , wherein the (b) cyclic amino acid comprises at least one aliphatic ring.
3. The composition according to Claim 1 or 2, wherein the (b) cyclic amino acid is selected from proline and proline derivatives.
4. The composition according to any one of the preceding claims, wherein the weight ratio of the (a) ascorbic acid and salts thereof to the (b) cyclic amino acid(s) is 1 to 100, preferably 1.5 to 75, and more preferable 2 to 50.
5. The composition according to any one of the preceding claims, wherein the composition has a pH of 2.5 to 7.5.
6. The composition according to any one of the preceding claims, wherein the composition is in the form of a single-phase solution.
7. The composition according to any one of the preceding claims, wherein the composition further comprises water.
8. The composition according to claim 7, wherein the amount of the water is 5% by weight or more, preferably 10% by weight or more, more preferably 15% by weight or more, and even more preferably 20% by weight or more, and is 80% or less, preferably 70% by weight or less, more preferably 60% by weight or less, even more preferably 50% by weight or less, and in particular 40% by weight or less, relative to the total weight of the composition.
9. The composition according to any one of the preceding claims, wherein the composition further comprises at least one hydrophilic organic solvent.
10. The composition according to claim 9, wherein the amount of the hydrophilic organic solvent(s) is 1% by weight or more, preferably 5% by weight or more, more preferably 10% by weight or more, even more preferably 20% by weight or more, and in particular 30% by weight or more, and is 70% by weight or less, preferably 60% by weight or less, and more preferably 50% by weight or less, relative to the total weight of the composition.
11. The composition according to any one of the preceding claims, wherein the composition comprises additional cosmetically active ingredients.
12. The composition according to any one of the preceding claims, wherein the composition comprises particulate materials in an amount of less than 5% by weight or less, preferably 3% by weight or less, more preferably 1% by weight or less, even more
preferably 0.5% by weight or less, and in particular 0.1% by weight or less, relative to the total weight of the composition, or the composition is free of any particulate materials.
13. The composition according to any one of the preceding claims, wherein the composition comprises surfactants in an amount of less than 5% by weight or less, preferably 3% by weight or less, more preferably 1% by weight or less, even more preferably 0.5% by weight or less, and in particular 0.1% by weight or less, relative to the total weight of the composition, or the composition is free of any surfactants.
14. A non-therapeutic cosmetic process for caring for and/or conditioning keratinous substances, such as skin, comprising: applying onto the keratinous substances a composition comprising:
(a) at least one of ascorbic acid and salts thereof in an amount of 15% by weight or more relative to the total weight of the composition; and
(b) at least one cyclic amino acid in an amount of 1% by weight or more relative to the total weight of the composition.
15. A use of (b) at least one cyclic amino acid in an amount of 1 % by weight or more relative to the total weight of the composition to obtain a stable aqueous composition comprising (a) at least one of ascorbic acid and salts thereof in an amount of 15% by weight or more relative to the total weight of the composition.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2020202536A JP2022090263A (en) | 2020-12-07 | 2020-12-07 | Compositions Containing Ascorbic Acid and Cyclic Amino Acids |
| JP2020-202536 | 2020-12-07 | ||
| FR2100214 | 2021-01-11 | ||
| FR2100214A FR3118710B1 (en) | 2021-01-11 | 2021-01-11 | COMPOSITION COMPRISING ASCORBIC ACID AND CYCLIC AMINO ACID |
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| Publication Number | Publication Date |
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| WO2022124386A1 true WO2022124386A1 (en) | 2022-06-16 |
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| Application Number | Title | Priority Date | Filing Date |
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| PCT/JP2021/045429 Ceased WO2022124386A1 (en) | 2020-12-07 | 2021-12-03 | Composition comprising ascorbic acid and cyclic amino acid |
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Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4647453A (en) * | 1984-10-18 | 1987-03-03 | Peritain, Ltd. | Treatment for tissue degenerative inflammatory disease |
| US4938969A (en) * | 1988-11-14 | 1990-07-03 | Milor Scientific, Ltd. | Method for the treatment of aging or photo-damaged skin |
| CA1325774C (en) * | 1987-01-27 | 1994-01-04 | James M. Wilmott | Cosmetic preparation incorporating stabilized ascorbic acid |
| US20030170319A1 (en) * | 2002-01-11 | 2003-09-11 | Shrirang Netke | Nutrient pharmaceutical formulation comprising polyphenols and use in treatment of cancer |
| EP1195159B1 (en) * | 2000-10-09 | 2006-05-31 | Rath, Matthias, Dr. med. | Therapeutic combination of ascorbate with lysine and arginine for prevention and treatment of cancer |
| WO2006108430A1 (en) * | 2005-04-11 | 2006-10-19 | Matthias Rath | Nutrient composition comprising green tea polyphenols for treating osteosarcoma |
| US7179841B2 (en) | 2004-01-13 | 2007-02-20 | L'oreal Usa Creative, Inc. | Stabilized ascorbic acid compositions and methods therefor |
| WO2014041528A2 (en) * | 2012-09-14 | 2014-03-20 | Martin Roslain Margaret | A composition |
| JP2018138617A (en) | 2016-06-28 | 2018-09-06 | ロート製薬株式会社 | External composition containing ascorbic acid and/or salt thereof |
| WO2019131892A1 (en) | 2017-12-27 | 2019-07-04 | ロート製薬株式会社 | External composition containing ascorbic acid and/or salt thereof |
-
2021
- 2021-12-03 WO PCT/JP2021/045429 patent/WO2022124386A1/en not_active Ceased
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4647453A (en) * | 1984-10-18 | 1987-03-03 | Peritain, Ltd. | Treatment for tissue degenerative inflammatory disease |
| CA1325774C (en) * | 1987-01-27 | 1994-01-04 | James M. Wilmott | Cosmetic preparation incorporating stabilized ascorbic acid |
| US4938969A (en) * | 1988-11-14 | 1990-07-03 | Milor Scientific, Ltd. | Method for the treatment of aging or photo-damaged skin |
| EP1195159B1 (en) * | 2000-10-09 | 2006-05-31 | Rath, Matthias, Dr. med. | Therapeutic combination of ascorbate with lysine and arginine for prevention and treatment of cancer |
| US20030170319A1 (en) * | 2002-01-11 | 2003-09-11 | Shrirang Netke | Nutrient pharmaceutical formulation comprising polyphenols and use in treatment of cancer |
| US7179841B2 (en) | 2004-01-13 | 2007-02-20 | L'oreal Usa Creative, Inc. | Stabilized ascorbic acid compositions and methods therefor |
| WO2006108430A1 (en) * | 2005-04-11 | 2006-10-19 | Matthias Rath | Nutrient composition comprising green tea polyphenols for treating osteosarcoma |
| WO2014041528A2 (en) * | 2012-09-14 | 2014-03-20 | Martin Roslain Margaret | A composition |
| JP2018138617A (en) | 2016-06-28 | 2018-09-06 | ロート製薬株式会社 | External composition containing ascorbic acid and/or salt thereof |
| WO2019131892A1 (en) | 2017-12-27 | 2019-07-04 | ロート製薬株式会社 | External composition containing ascorbic acid and/or salt thereof |
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