WO2023063106A1 - Cosmetic - Google Patents

Cosmetic Download PDF

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Publication number
WO2023063106A1
WO2023063106A1 PCT/JP2022/036654 JP2022036654W WO2023063106A1 WO 2023063106 A1 WO2023063106 A1 WO 2023063106A1 JP 2022036654 W JP2022036654 W JP 2022036654W WO 2023063106 A1 WO2023063106 A1 WO 2023063106A1
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Prior art keywords
acid
cosmetic
oil
molecular weight
component
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PCT/JP2022/036654
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French (fr)
Japanese (ja)
Inventor
友香 水野
育浩 鈴木
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株式会社 資生堂
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Application filed by 株式会社 資生堂 filed Critical 株式会社 資生堂
Priority to CN202280061802.6A priority Critical patent/CN117999060A/en
Priority to JP2023555111A priority patent/JPWO2023063106A1/ja
Publication of WO2023063106A1 publication Critical patent/WO2023063106A1/en

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin

Definitions

  • the present invention relates to a cosmetic comprising a cyclic carboxamide derivative having a specific structure or a salt thereof and a polyacrylic acid having a controlled molecular weight distribution or a salt thereof.
  • a cyclic carboxamide derivative represented by formula (1) or a salt thereof (In the formula, R 1 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom, X is —CH 2 — or —N(R 2 )—, wherein R 2 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom, and n is an integer of 1 to 3), and (B) a polyacrylic acid having a weight average molecular weight of 500,000 to 8,000,000 and a content of a compound having a molecular weight of 10,000,000 or more is 10% by mass or less, or Cosmetics containing the salt.
  • R 1 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom
  • X is —CH 2 — or —N(R 2 )—, wherein R 2 is a
  • R 1 is a hydroxyalkyl group having 1 to 3 carbon atoms
  • [5] The cosmetic according to any one of [1] to [4], wherein the amount of component (B) is 0.001 to 0.5% by mass relative to the total amount of the cosmetic.
  • [6] The cosmetic according to any one of [1] to [5], further comprising (C) diglycerin.
  • the present invention it is possible to provide cosmetics with excellent usability.
  • it quickly absorbs into the skin, imparts freshness without sliminess during application, and imparts a moist feeling to the skin without stickiness after application.
  • the present invention relates to a cosmetic comprising (A) a cyclic carboxamide derivative having a specific structure or a salt thereof, and (B) polyacrylic acid or a salt thereof having a controlled molecular weight distribution.
  • the cosmetic according to the present invention is a cyclic carboxamide derivative represented by formula (1) or a salt thereof (hereinafter sometimes referred to as component (A). The same applies to other components). There is.).
  • component (A) Cyclic carboxamide derivative or salt thereof
  • R 1 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom
  • X is —CH 2 — or —N(R 2 )—
  • R 2 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom
  • n is an integer of 1-3.
  • the above hydrocarbon group is not particularly limited, and may be, for example, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cycloalkylalkyl group, a haloalkyl group, an alkoxyalkyl group, or an alkoxycarbonylalkyl group, preferably is an alkyl group.
  • R 1 is a hydroxyalkyl group having 1 to 3 carbon atoms
  • X is —CH 2 — or —NH—
  • n is 1.
  • Specific examples of the cyclic carboxamide derivative represented by formula (1) include the following.
  • Component (A) is most preferably 1-(2-hydroxyethyl)-2-imidazolidinone.
  • the (A) component may be a salt of the cyclic carboxamide derivative represented by formula (1).
  • the type of salt is not particularly limited as long as it is a pharmacologically acceptable salt, and may be an inorganic salt or an organic salt.
  • inorganic salts include hydrochlorides, sulfates, phosphates, hydrobromides, sodium salts, potassium salts, magnesium salts, calcium salts, magnesium salts, ammonium salts and the like.
  • organic salts include acetates, lactates, maleates, fumarates, tartrates, methanesulfonates, p-toluenesulfonates, triethanolamine salts, amino acid salts and the like.
  • component (A) component can be blended one or two or more.
  • the blending amount of component (A) is preferably 0.05 to 7% by mass, more preferably 0.1 to 6% by mass, and still more preferably 0.3 to 3%, based on the total amount of the cosmetic. % by mass.
  • the cosmetic according to the present invention comprises (B) polyacrylic acid with a controlled molecular weight distribution or a salt thereof.
  • Component (B) has (i) a weight average molecular weight of 500,000 to 8,000,000 and (ii) a compound having a molecular weight of 10,000,000 or more. It is a water-soluble polymer
  • the weight average molecular weight of component (B) (i) is 500,000 or more, more preferably 800,000 or more, still more preferably 1,000,000 or more, and is 8,000,000 or less, more preferably 5,000,000 or less, and still more preferably. is less than 3 million. If the weight-average molecular weight is less than 500,000, the spreadability of the cosmetic composition tends to be poor. Because it becomes difficult.
  • component (ii) In the molecular weight distribution of polyacrylic acid or a salt thereof, if the content of compounds having a molecular weight of 10 million or more is 10% by mass or less of the total amount of component (B), the stickiness caused by component (A) can be suppressed. It is possible to sufficiently improve the freshness and moistness after application. On the other hand, when the ratio of the huge compound having a molecular weight of 10,000,000 or more exceeds 10% by mass, it tends to be difficult to suppress deterioration in usability due to the addition of component (A).
  • polyacrylic acid or its salt will be specifically described, but synthetic polymer compounds other than these that satisfy the above conditions (i) and (ii) are (B).
  • Monomers constituting such polymer compounds include acrylic acid-based monomers such as methacrylic acid, alkyl acrylates, alkyl methacrylates, and acrylic acid esters.
  • a macromonomer obtained by adding polyethylene glycol, a silicone-based polymer compound, or the like as a side chain to the above-mentioned monomer can also be preferably used as a structural unit.
  • Types of salts include alkali metal salts (e.g., sodium salts, potassium salts, magnesium salts, calcium salts, etc.), organic amine salts (e.g., monoethanolamine salts, diethanolamine salts, triethanolamine salts, triisopropanolamine salts, etc.). ), and 2-amino-2-methyl-1-propanol, 2-amino-2-methyl-1,3-propanediol, 2-amino-2-hydroxymethyl-1,3-propanediol, L-arginine, Examples thereof include salts of basic nitrogen-containing compounds such as L-lysine and L-alkyltaurine. Among these, monovalent alkali metal salts and organic amine salts are preferred, sodium salts, potassium salts and triethanolamine salts are more preferred, and sodium salts are even more preferred.
  • alkali metal salts e.g., sodium salts, potassium salts, magnesium salts, calcium salts, etc.
  • the (B) component can be synthesized by a known living polymerization method.
  • the reversible addition-fragmentation chain transfer polymerization method (RAFT polymerization method) is preferable because it enables the synthesis of compounds with a narrow molecular weight distribution.
  • RAFT polymerization method reversible addition-fragmentation chain transfer polymerization method
  • the description of WO2015/052804 can be referred for the detail of the manufacturing method of a component.
  • the molecular weight of component (B) can be measured by known methods such as light scattering, ultracentrifugation, and chromatography for the weight average molecular weight, and osmotic pressure and chromatography for the number average molecular weight.
  • the chromatography method is preferable in that the weight average molecular weight, number average molecular weight, molecular weight distribution, and polydispersity can be easily obtained with a small amount of sample, and the gel permeation chromatography method (hereinafter abbreviated as GPC). ) is preferred.
  • GPC gel permeation chromatography method
  • the polydispersity can be expressed as a value obtained by dividing the weight average molecular weight obtained by GPC analysis by the number average molecular weight.
  • the blending amount of component (B) is preferably 0.001 to 0.5% by mass, more preferably 0.005 to 0.3% by mass, and still more preferably 0% by mass, relative to the total amount of the cosmetic. 0.01 to 0.2% by mass.
  • the cosmetic according to the present invention may further contain (C) diglycerin.
  • the blending amount of component (C) is preferably 0.1 to 5% by mass, more preferably 0.3 to 3% by mass, and still more preferably 0.5 to 2%, based on the total amount of the cosmetic. % by mass. By blending the component (C) within this range, it is possible to further improve the feeling of use, such as freshness during application.
  • the cosmetic according to the present invention can further contain (D) a sugar alcohol selected from the group consisting of mannitol, xylitol, erythritol, sorbitol, maltitol, and inositol. Among them, maltitol and xylitol are most suitable.
  • a sugar alcohol selected from the group consisting of mannitol, xylitol, erythritol, sorbitol, maltitol, and inositol.
  • maltitol and xylitol are most suitable.
  • These derivatives, such as POE and/or POP adducts, alkyl group adducts, cationized products, anionized products, silylated products, etc. can also be used as component (D).
  • POE represents polyoxyethylene
  • POP represents polyoxypropylene.
  • component (D) component can be blended in one or more.
  • the blending amount of component (D) is preferably 0.1 to 5% by mass, more preferably 0.3 to 3% by mass, and still more preferably 0.5 to 2%, based on the total amount of the cosmetic. % by mass.
  • the cosmetic according to the present invention may further contain (E) polyethylene glycol (PEG).
  • Component (E) includes, for example, PEG-6, PEG-32, PEG-400 and the like.
  • (E) component can be blended 1 type(s) or 2 or more types.
  • the blending amount of component (E) is preferably 0.1 to 5% by mass, more preferably 0.3 to 3% by mass, and still more preferably 0.5 to 2%, based on the total amount of the cosmetic. % by mass.
  • the cosmetic composition of the present invention contains other ingredients such as aqueous solvents, water-soluble polymers, surfactants, moisturizers, oils, UV absorbers, drugs, and chelating agents as long as the effects of the present invention are not impaired. , preservatives, pH adjusters, antioxidants, powders, fragrances, coloring agents, pigments, etc., can be appropriately blended as necessary.
  • the surfactant can be arbitrarily selected from nonionic surfactants, cationic surfactants, anionic surfactants, and amphoteric surfactants.
  • moisturizing agents examples include propylene glycol, dipropylene glycol, glycerin, 1,3-butylene glycol, chondroitin sulfate, hyaluronic acid, mucoitin sulfate, caronin acid, atelocollagen, cholesteryl-12-hydroxystearate, sodium lactate, and bile acid. salts, Dl-pyrrolidone carboxylates, alkylene oxide derivatives, short-chain soluble collagen, diglycerin (EO) PO adducts and the like.
  • EO represents ethylene oxide
  • PO propylene oxide.
  • the oil is not particularly limited, and various oils widely used in cosmetics can be blended, regardless of whether they are solid or liquid.
  • a solid oil is an oil that is solid or semi-solid at room temperature and is generally used in cosmetics.
  • oils include cacao butter, coconut oil, horse oil, hydrogenated coconut oil, palm oil, beef tallow, sheep oil, hydrogenated beef tallow, palm kernel oil, pork oil, beef bone oil, Japanese wax kernel oil, hydrogenated oil, Solid oils and fats such as beef leg fat, Japanese wax, hydrogenated castor oil; beeswax, candelilla wax, cotton wax, carnauba wax, bayberry wax, privet wax, whale wax, montan wax, bran wax, lanolin, kapok wax, lanolin acetate, sugarcane wax, lanolin fatty acid isopropyl, Waxes such as hexyl laurate, reduced lanolin, jojoba wax, hard lanolin, shellac wax, POE lanolin alcohol ether, POE lanolin alcohol acetate, POE cholesterol ether, POE hydrogenated lanolin alcohol ether; polyethylene wax, paraffin wax,
  • a liquid oil is an oil that is liquid at room temperature and is generally used in cosmetics.
  • oils include, for example, avocado oil, evening primrose oil, camellia oil, turtle oil, macadamia nut oil, sunflower oil, almond oil, corn oil, mink oil, olive oil, rapeseed oil, egg yolk oil, sesame oil, persic oil, and wheat germ.
  • Liquid fats and oils cetyl octanoate, cetyl 2-ethylhexanoate, hexyldecyl dimethyloctanoate, ethyl laurate, hexyl laurate, isopropyl myristate, 2-hexyldecyl myristate, myristyl myristate, octyldodecyl myristate, palmitic acid Isopropyl acid, 2-ethylhexyl palmitate, 2-hexyldecyl palmitate, 2-heptylundecyl palmitate, butyl stearate, isocetyl stearate, isocetyl isostearate, decyl oleate, dodecyl oleate, oleyl oleate, myristyl lactate , cetyl lactate, diisostearyl malate, cholesteryl 12-hydroxy
  • ultraviolet absorbers examples include benzoic acid-based ultraviolet absorbers such as para-aminobenzoic acid; anthranilic acid-based ultraviolet absorbers such as methyl anthranilate; salicylic acid-based ultraviolet absorbers such as octyl salicylate; Cinnamic acid UV absorbers such as octyl formate; pyridazine derivatives such as dimorpholinopyridazinone; benzoylmethane derivatives such as 4-methoxy-4'-t-butyldibenzoylmethane; 3-(4'-methylbenzylidene )-D,l-camphor, 3-benzylidene-D,l-camphor and other camphor derivatives; 2,2′-hydroxy-5-methylphenylbenzotriazole, 2-(2′-hydroxy-5′-t-octyl Benzotriazole derivatives such as phenyl)benzotriazole, 2-(2'-hydroxy-5'-methylphenylbenzotriazo
  • Drugs include, for example, ascorbic acid (vitamin C), tranexamic acid, kojic acid, ellagic acid, arbutin, alkoxysalicylic acid, glycyrrhizic acid, tocopherol, retinol and derivatives thereof (e.g., ascorbic acid (vitamin C), tranexamic acid, kojic acid, ellagic acid, arbutin, alkoxysalicylic acid, glycyrrhizic acid, tocopherol, retinol and derivatives thereof (e.g.
  • L-ascorbate L-ascorbic acid ester magnesium salt
  • L-ascorbic acid 2-glucoside ascorbyl glucoside
  • 2-O-ethyl-L-ascorbic acid 3-O-ethyl-L-ascorbic acid
  • 4-methoxysalicylic acid sodium salt 4-methoxy potassium salicylate, dipotassium glycyrrhizinate, stearyl glycyrrhizinate, tocophenol acetate, retinol acetate, retinol palmitate, etc.).
  • Chelating agents include citramalic acid, agaric acid, glyceric acid, shikimic acid, hinokitiol, gallic acid, tannic acid, caffeic acid, ethylenediaminetetraacetic acid, ethyleneglycoldiaminetetraacetic acid, diethylenetriaminepentaacetic acid, phytic acid, polyphosphoric acid, and metaphosphoric acid. , and their analogues, alkali metal salts and carboxylic acid esters, and the like.
  • Preservatives include paraoxybenzoic acid esters such as methylparaben, ethylparaben, and butylparaben, benzoic acid, salicylic acid, sorbic acid, parachlorometacresol, hexachlorophen, benzalkonium chloride, chlorhexidine chloride, trichlorocarbanilide, and photosensitizers. and phenoxyethanol.
  • pH adjusters examples include buffers such as lactic acid-sodium lactate, citric acid-sodium citrate, and succinic acid-sodium succinate.
  • antioxidants include carotenoids, dibutylhydroxytoluene, butylhydroxyanisole, sodium pyrosulfite, and gallic acid esters.
  • Cosmetics according to the present invention include pharmaceuticals, quasi-drugs (ointments, etc.), and basic cosmetics such as facial cleansers, lotions, milky lotions, creams, gels, essences (beauty liquids), packs, and masks; foundations and lipsticks. sun care products such as sunscreen; aromatic cosmetics; body cosmetics, and the like. These forms are merely examples, and the cosmetic according to the present invention is not limited to these forms.
  • ⁇ Usability evaluation> A panel of 10 specialists applied the sample to the face and evaluated usability (quickness of familiarity with the skin during application, lack of sliminess during application, freshness during application, non-stickiness of skin after application, after application). Moistness of the skin) was evaluated. Based on the evaluation by each expert panel, the samples were judged according to the following criteria.
  • Examples 1 to 15 and Comparative Examples 1 to 3 Cosmetics of Examples 1 to 15 and Comparative Examples 1 to 3 were prepared by a conventional method with formulations shown in Tables 1 and 2, and evaluated for the above items (1) to (5).
  • * 1 Sodium polyacrylate having a weight average molecular weight of 2 million and a content of macromolecules with a molecular weight of 10 million or more is 10% by mass or less
  • * 2 Aronbis (registered trademark) SX (manufactured by Toagosei Co., Ltd.)

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Abstract

[Problem] To provide a cosmetic having excellent afterfeel. [Solution] The present invention provides a cosmetic comprising: (A) a cyclic carboxamide derivative having a specific structure, or a salt thereof; and (B) a polyacrylic acid having a controlled molecular weight distribution, or a salt thereof.

Description

化粧料cosmetics
 本発明は、特定の構造を有する環状カルボキサミド誘導体またはその塩、および分子量分布が制御されたポリアクリル酸またはその塩を含んでなる化粧料に関する。 The present invention relates to a cosmetic comprising a cyclic carboxamide derivative having a specific structure or a salt thereof and a polyacrylic acid having a controlled molecular weight distribution or a salt thereof.
 化粧料において、分子量分布が制御されたポリアクリル酸またはその塩が増粘剤として配合され、曳糸性を軽減し、塗布中のぬるつきや塗布後のべたつきを抑制できることが知られている(特許文献1)。このような化粧料について、使用者はより優れた使用感を有することを求めており、さらなる使用感の改善の余地があった。 In cosmetics, it is known that polyacrylic acid or a salt thereof with a controlled molecular weight distribution is blended as a thickener to reduce stringiness and suppress sliminess during application and stickiness after application ( Patent document 1). With regard to such cosmetics, users are demanding that they have a better feeling during use, and there is room for further improvement in the feeling during use.
 一方、環状カルボキサミド誘導体は、抗しわ効果や色素沈着抑制効果があることが知られており、化粧料等に配合することが提案されている(特許文献2)。 On the other hand, cyclic carboxamide derivatives are known to have anti-wrinkle and anti-pigmentation effects, and have been proposed to be added to cosmetics (Patent Document 2).
国際公開2015/052804International publication 2015/052804 国際公開2011/040496International publication 2011/040496
 本発明者らの検討によると、環状カルボキサミド誘導体を化粧料に用いる場合に、塗布中の肌へのなじみが遅い傾向にあることがわかってきた。本発明者らは、分子量分布が制御されたポリアクリルと特定の環状カルボキサミド誘導体との組み合わせを含む化粧料を用いることで、驚くべきことに、肌なじみが改善され、さらに優れた使用感も同時に達成できることを見いだした。本発明はこれらの知見に基づくものである。 According to the studies of the present inventors, it has been found that when cyclic carboxamide derivatives are used in cosmetics, they tend to be slow to absorb into the skin during application. The present inventors have surprisingly found that by using a cosmetic containing a combination of a polyacryl with a controlled molecular weight distribution and a specific cyclic carboxamide derivative, the skin familiarity is improved, and at the same time, the feeling of use is excellent. I have found what I can achieve. The present invention is based on these findings.
 本発明によれば、以下の発明が提供される。
[1](A)式(1)で表される環状カルボキサミド誘導体またはその塩
Figure JPOXMLDOC01-appb-C000002
(式中、
 Rは、水酸基で置換されていてもよい炭素数1~6の炭化水素基、または水素原子であり、
 Xは、-CH-または-N(R)-であり、ここで、Rは、水酸基で置換されていてもよい炭素数1~6の炭化水素基、または水素原子であり、かつ
 nは、1~3の整数である)、および
(B)重量平均分子量が50万~800万であり、分子量が1000万以上である化合物の含有量が10質量%以下であるポリアクリル酸またはその塩
を含んでなる、化粧料。
[2](A)成分の式(1)において、
 Rが、炭素数1~3のヒドロキシアルキル基であり、
 Xが、-CH-または-NH-であり、かつ
 nが、1である、[1]に記載の化粧料。
[3](A)成分が、1-(2-ヒドロキシエチル)-2-イミダゾリジノンである、[1]または[2]に記載の化粧料。
[4](A)成分の配合量が、化粧料の総量に対して、0.05~7質量%である、[1]~[3]のいずれかに記載の化粧料。
[5](B)成分の配合量が、化粧料の総量に対して、0.001~0.5質量%である、[1]~[4]のいずれかに記載の化粧料。
[6](C)ジグリセリンをさらに含んでなる、[1]~[5]のいずれかに記載の化粧料。
[7](D)マンニトール、キシリトール、エリスリトール、ソルビトール、マルチトール、およびイノシトールからなる群から選択される糖アルコールをさらに含む、[1]~[6]のいずれかに記載の化粧料。
[8](E)ポリエチレングリコールをさらに含んでなる、[1]~[7]のいずれかに記載の化粧料。
According to the present invention, the following inventions are provided.
[1] (A) a cyclic carboxamide derivative represented by formula (1) or a salt thereof
Figure JPOXMLDOC01-appb-C000002
(In the formula,
R 1 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom,
X is —CH 2 — or —N(R 2 )—, wherein R 2 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom, and n is an integer of 1 to 3), and (B) a polyacrylic acid having a weight average molecular weight of 500,000 to 8,000,000 and a content of a compound having a molecular weight of 10,000,000 or more is 10% by mass or less, or Cosmetics containing the salt.
[2] In the formula (1) of the component (A),
R 1 is a hydroxyalkyl group having 1 to 3 carbon atoms,
The cosmetic according to [1], wherein X is —CH 2 — or —NH—, and n is 1.
[3] The cosmetic of [1] or [2], wherein component (A) is 1-(2-hydroxyethyl)-2-imidazolidinone.
[4] The cosmetic according to any one of [1] to [3], wherein the amount of component (A) is 0.05 to 7% by mass relative to the total amount of the cosmetic.
[5] The cosmetic according to any one of [1] to [4], wherein the amount of component (B) is 0.001 to 0.5% by mass relative to the total amount of the cosmetic.
[6] The cosmetic according to any one of [1] to [5], further comprising (C) diglycerin.
[7] (D) The cosmetic of any one of [1] to [6], further comprising a sugar alcohol selected from the group consisting of mannitol, xylitol, erythritol, sorbitol, maltitol, and inositol.
[8] (E) The cosmetic according to any one of [1] to [7], further comprising polyethylene glycol.
 本発明によれば、使用感に優れた化粧料を提供することができる。特に、塗布中は、肌へのなじみがはやく、ぬるつきがなく、みずみずしさを付与し、塗布後はべたつきがなく、肌にしっとり感を付与することができる。 According to the present invention, it is possible to provide cosmetics with excellent usability. In particular, it quickly absorbs into the skin, imparts freshness without sliminess during application, and imparts a moist feeling to the skin without stickiness after application.
発明の具体的説明Specific description of the invention
 本発明は、(A)特定の構造を有する環状カルボキサミド誘導体またはその塩、および(B)分子量分布が制御されたポリアクリル酸またはその塩を含んでなる化粧料に関するものである。 The present invention relates to a cosmetic comprising (A) a cyclic carboxamide derivative having a specific structure or a salt thereof, and (B) polyacrylic acid or a salt thereof having a controlled molecular weight distribution.
(A)環状カルボキサミド誘導体またはその塩
 本発明による化粧料は、式(1)で表される環状カルボキサミド誘導体またはその塩(以下、(A)成分と称することがある。他の成分についても同様である。)を含んでなる。
Figure JPOXMLDOC01-appb-C000003
式中、
 Rは、水酸基で置換されていてもよい炭素数1~6の炭化水素基、または水素原子であり、
 Xは、-CH-または-N(R)-であり、ここで、Rは、水酸基で置換されていてもよい炭素数1~6の炭化水素基、または水素原子であり、かつ
 nは、1~3の整数である。
 上記の炭化水素基は、特に限定されず、例えば、アルキル基、シクロアルキル基、アルケニル基、アルキニル基、シクロアルキルアルキル基、ハロアルキル基、アルコキシアルキル基、アルコキシカルボニルアルキル基であってよく、好ましくはアルキル基である。
(A) Cyclic carboxamide derivative or salt thereof The cosmetic according to the present invention is a cyclic carboxamide derivative represented by formula (1) or a salt thereof (hereinafter sometimes referred to as component (A). The same applies to other components). There is.).
Figure JPOXMLDOC01-appb-C000003
During the ceremony,
R 1 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom,
X is —CH 2 — or —N(R 2 )—, wherein R 2 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom, and n is an integer of 1-3.
The above hydrocarbon group is not particularly limited, and may be, for example, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cycloalkylalkyl group, a haloalkyl group, an alkoxyalkyl group, or an alkoxycarbonylalkyl group, preferably is an alkyl group.
 好ましい形態において、(A)成分の式(1)において、
 Rが、炭素数1~3のヒドロキシアルキル基であり、
 Xが、-CH-または-NH-であり、かつ
 nが、1である。
 式(1)で表される環状カルボキサミド誘導体の具体例としては、例えば、以下が挙げられる。
Figure JPOXMLDOC01-appb-C000004
 (A)成分は、最も好ましくは、1-(2-ヒドロキシエチル)-2-イミダゾリジノンである。
In a preferred form, in the formula (1) of component (A),
R 1 is a hydroxyalkyl group having 1 to 3 carbon atoms,
X is —CH 2 — or —NH—, and n is 1.
Specific examples of the cyclic carboxamide derivative represented by formula (1) include the following.
Figure JPOXMLDOC01-appb-C000004
Component (A) is most preferably 1-(2-hydroxyethyl)-2-imidazolidinone.
 (A)成分は、式(1)で表される環状カルボキサミド誘導体の塩であってもよい。塩の種類は、薬理学的に許容される塩であれば特に限定されず、無機塩であっても有機塩であってもよい。無機塩としては、例えば、塩酸塩、硫酸塩、リン酸塩、臭化水素酸塩、ナトリウム塩、カリウム塩、マグネシウム塩、カルシウム塩、マグネシウム塩、アンモニウム塩等が挙げられる。有機塩としては、例えば、酢酸塩、乳酸塩、マレイン酸塩、フマル酸塩、酒石酸塩、メタンスルホン酸塩、p-トルエンスルホン酸塩、トリエタノールアミン塩、アミノ酸塩等が挙げられる。 The (A) component may be a salt of the cyclic carboxamide derivative represented by formula (1). The type of salt is not particularly limited as long as it is a pharmacologically acceptable salt, and may be an inorganic salt or an organic salt. Examples of inorganic salts include hydrochlorides, sulfates, phosphates, hydrobromides, sodium salts, potassium salts, magnesium salts, calcium salts, magnesium salts, ammonium salts and the like. Examples of organic salts include acetates, lactates, maleates, fumarates, tartrates, methanesulfonates, p-toluenesulfonates, triethanolamine salts, amino acid salts and the like.
 (A)成分は、1種または2種以上を配合することができる。(A)成分の配合量は、化粧料の総量に対して、好ましくは0.05~7質量%であり、より好ましくは0.1~6質量%であり、さらに好ましくは0.3~3質量%である。 (A) component can be blended one or two or more. The blending amount of component (A) is preferably 0.05 to 7% by mass, more preferably 0.1 to 6% by mass, and still more preferably 0.3 to 3%, based on the total amount of the cosmetic. % by mass.
(B)分子量分布が制御されたポリアクリル酸またはその塩
 本発明による化粧料は、(B)分子量分布が制御されたポリアクリル酸またはその塩を含んでなる。(B)成分は、(i)重量平均分子量が50万~800万であり、かつ、(ii)分子量が1000万以上である化合物の含有量が10質量%以下であるように分子量分布が制御された水溶性ポリマーである。
 (B)成分の(i)重量平均分子量は、50万以上、より好ましくは80万以上、さらに好ましくは100万以上であり、かつ、800万以下、より好ましくは500万以下であり、さらに好ましくは300万以下である。重量平均分子量が50万未満では化粧料ののびが悪くなる傾向があり、また、800万を超えると、分子量が1000万以上である化合物の含有量を10質量%以下に抑えることが技術的に難しくなるからである。
(B) Polyacrylic acid with controlled molecular weight distribution or a salt thereof The cosmetic according to the present invention comprises (B) polyacrylic acid with a controlled molecular weight distribution or a salt thereof. Component (B) has (i) a weight average molecular weight of 500,000 to 8,000,000 and (ii) a compound having a molecular weight of 10,000,000 or more. It is a water-soluble polymer
The weight average molecular weight of component (B) (i) is 500,000 or more, more preferably 800,000 or more, still more preferably 1,000,000 or more, and is 8,000,000 or less, more preferably 5,000,000 or less, and still more preferably. is less than 3 million. If the weight-average molecular weight is less than 500,000, the spreadability of the cosmetic composition tends to be poor. Because it becomes difficult.
 (ii)ポリアクリル酸またはその塩の分子量分布において、分子量が1000万以上の化合物の含有量が(B)成分全体の10質量%以下であれば、(A)成分によって引き起こされるべたつきを抑えることができ、塗布後のみずみずしさやしっとりさを十分に改善することができる。一方、分子量が1000万以上の巨大な化合物の割合が10質量%を超えると、(A)成分の配合による使用性の低下を抑えるのが難しくなる傾向がある。
 (B)成分の主たる高分子鎖は直鎖状であることが好ましい。さらに、(B)成分の分子量分布の多分散度(=重量平均分子量/数平均分子量)は好ましくは2以下であり、より好ましくは1.8以下である。
(ii) In the molecular weight distribution of polyacrylic acid or a salt thereof, if the content of compounds having a molecular weight of 10 million or more is 10% by mass or less of the total amount of component (B), the stickiness caused by component (A) can be suppressed. It is possible to sufficiently improve the freshness and moistness after application. On the other hand, when the ratio of the huge compound having a molecular weight of 10,000,000 or more exceeds 10% by mass, it tends to be difficult to suppress deterioration in usability due to the addition of component (A).
The main polymer chain of component (B) is preferably linear. Furthermore, the polydispersity (=weight average molecular weight/number average molecular weight) of the molecular weight distribution of component (B) is preferably 2 or less, more preferably 1.8 or less.
 本明細書では、ポリアクリル酸またはその塩についてのみ具体的に説明するが、これら以外の合成高分子化合物であっても、上記(i)および(ii)の条件を満たすものは、(B)成分と同様に(A)成分によるべたつき等の軽減が可能である。このような高分子化合物を構成するモノマーとしては、メタクリル酸、アクリル酸アルキル、メタクリル酸アルキル、アクリル酸エステル等のアクリル酸系モノマーが挙げられる。また、前記モノマーに、側鎖としてポリエチレングリコール、シリコーン系高分子化合物等が付加されたマクロモノマーも、構成単位として好適に用いることができる。 In this specification, only polyacrylic acid or its salt will be specifically described, but synthetic polymer compounds other than these that satisfy the above conditions (i) and (ii) are (B). Like the component (A), it is possible to reduce stickiness and the like. Monomers constituting such polymer compounds include acrylic acid-based monomers such as methacrylic acid, alkyl acrylates, alkyl methacrylates, and acrylic acid esters. A macromonomer obtained by adding polyethylene glycol, a silicone-based polymer compound, or the like as a side chain to the above-mentioned monomer can also be preferably used as a structural unit.
 塩の種類としては、アルカリ金属塩(例えば、ナトリウム塩、カリウム塩、マグネシウム塩、カルシウム塩等)、有機アミン塩(例えば、モノエタノールアミン塩、ジエタノールアミン塩、トリエタノールアミン塩、トリイソプロパノールアミン塩等)、および2-アミノ-2-メチル-1-プロパノール、2-アミノ-2-メチル-1、3-プロパンジオール、2-アミノ-2-ヒドロキシメチル-1、3-プロパンジオール、L-アルギニン、L-リジン、L-アルキルタウリン等の塩基性窒素含有化合物の塩等が挙げられる。このうち、一価のアルカリ金属塩および有機アミン塩が好ましく、より好ましくはナトリウム塩、カリウム塩、トリエタノールアミン塩であり、さらに好ましくはナトリウム塩である。 Types of salts include alkali metal salts (e.g., sodium salts, potassium salts, magnesium salts, calcium salts, etc.), organic amine salts (e.g., monoethanolamine salts, diethanolamine salts, triethanolamine salts, triisopropanolamine salts, etc.). ), and 2-amino-2-methyl-1-propanol, 2-amino-2-methyl-1,3-propanediol, 2-amino-2-hydroxymethyl-1,3-propanediol, L-arginine, Examples thereof include salts of basic nitrogen-containing compounds such as L-lysine and L-alkyltaurine. Among these, monovalent alkali metal salts and organic amine salts are preferred, sodium salts, potassium salts and triethanolamine salts are more preferred, and sodium salts are even more preferred.
 (B)成分は、公知のリビング重合法により合成することができる。なかでも、分子量分布の狭い化合物の合成が可能なことから可逆的付加-開裂連鎖移動重合法(RAFT重合法)が好ましい。(B)成分の製造方法の詳細については、WO2015/052804号の記載を参照することができる。 The (B) component can be synthesized by a known living polymerization method. Among them, the reversible addition-fragmentation chain transfer polymerization method (RAFT polymerization method) is preferable because it enables the synthesis of compounds with a narrow molecular weight distribution. (B) The description of WO2015/052804 can be referred for the detail of the manufacturing method of a component.
 (B)成分の分子量は、重量平均分子量については光散乱法、超遠心法、クロマトグラフィー法等、数平均分子量については浸透圧法、クロマトグラフィー法等の公知の方法によって測定することができる。なかでも、少量の試料で簡便に重量平均分子量、数平均分子量、分子量分布、および多分散度が得られる点でクロマトグラフィー法が好ましく、さらには、ゲルパーミエーションクロマトグラフ法(以下、GPCと略記)が好適である。多分散度は、GPC解析によって得られた重量平均分子量を数平均分子量で除した値で表記することができる。 The molecular weight of component (B) can be measured by known methods such as light scattering, ultracentrifugation, and chromatography for the weight average molecular weight, and osmotic pressure and chromatography for the number average molecular weight. Among them, the chromatography method is preferable in that the weight average molecular weight, number average molecular weight, molecular weight distribution, and polydispersity can be easily obtained with a small amount of sample, and the gel permeation chromatography method (hereinafter abbreviated as GPC). ) is preferred. The polydispersity can be expressed as a value obtained by dividing the weight average molecular weight obtained by GPC analysis by the number average molecular weight.
 (B)成分の配合量は、化粧料の総量に対して、好ましくは0.001~0.5質量%であり、より好ましくは0.005~0.3質量%であり、さらに好ましくは0.01~0.2質量%である。 The blending amount of component (B) is preferably 0.001 to 0.5% by mass, more preferably 0.005 to 0.3% by mass, and still more preferably 0% by mass, relative to the total amount of the cosmetic. 0.01 to 0.2% by mass.
(C)ジグリセリン
 本発明による化粧料は、(C)ジグリセリンをさらに含むことができる。
 (C)成分の配合量は、化粧料の総量に対して、好ましくは0.1~5質量%であり、より好ましくは0.3~3質量%であり、さらに好ましくは0.5~2質量%である。(C)成分をこの範囲で配合すれば、塗布中のみずみずしさなどの使用感をさらに向上させることができる。
(C) diglycerin The cosmetic according to the present invention may further contain (C) diglycerin.
The blending amount of component (C) is preferably 0.1 to 5% by mass, more preferably 0.3 to 3% by mass, and still more preferably 0.5 to 2%, based on the total amount of the cosmetic. % by mass. By blending the component (C) within this range, it is possible to further improve the feeling of use, such as freshness during application.
(D)糖アルコール
 本発明による化粧料は、(D)マンニトール、キシリトール、エリスリトール、ソルビトール、マルチトール、およびイノシトールからなる群から選択される糖アルコールをさらに含むことができる。なかでも、マルチトール、キシリトールが最適である。これらの誘導体、例えば、POEおよび/またはPOP付加物、アルキル基付加物、カチオン化物、アニオン化物、シリル化物なども(D)成分として用いることができる。なお、本明細書中、POEはポリオキシエチレン、POPはポリオキシプロピレンを表す。
(D) Sugar alcohol The cosmetic according to the present invention can further contain (D) a sugar alcohol selected from the group consisting of mannitol, xylitol, erythritol, sorbitol, maltitol, and inositol. Among them, maltitol and xylitol are most suitable. These derivatives, such as POE and/or POP adducts, alkyl group adducts, cationized products, anionized products, silylated products, etc., can also be used as component (D). In addition, in this specification, POE represents polyoxyethylene, and POP represents polyoxypropylene.
 (D)成分は1種または2種以上を配合することができる。(D)成分の配合量は、化粧料の総量に対して、好ましくは0.1~5質量%であり、より好ましくは0.3~3質量%であり、さらに好ましくは0.5~2質量%である。 (D) component can be blended in one or more. The blending amount of component (D) is preferably 0.1 to 5% by mass, more preferably 0.3 to 3% by mass, and still more preferably 0.5 to 2%, based on the total amount of the cosmetic. % by mass.
(E)ポリエチレングリコール
 本発明による化粧料は、(E)ポリエチレングリコール(PEG)をさらに含むことができる。(E)成分としては、例えば、PEG-6、PEG-32、PEG-400等が挙げられる。
 (E)成分は1種または2種以上を配合することができる。(E)成分の配合量は、化粧料の総量に対して、好ましくは0.1~5質量%であり、より好ましくは0.3~3質量%であり、さらに好ましくは0.5~2質量%である。
(E) Polyethylene glycol The cosmetic according to the present invention may further contain (E) polyethylene glycol (PEG). Component (E) includes, for example, PEG-6, PEG-32, PEG-400 and the like.
(E) component can be blended 1 type(s) or 2 or more types. The blending amount of component (E) is preferably 0.1 to 5% by mass, more preferably 0.3 to 3% by mass, and still more preferably 0.5 to 2%, based on the total amount of the cosmetic. % by mass.
<他の任意成分>
 本発明の化粧料は、本発明の効果を阻害しない範囲において、他の成分、例えば、水性溶媒、水溶性高分子、界面活性剤、保湿剤、油分、紫外線吸収剤、薬剤のほか、キレート剤、防腐剤、pH調整剤、酸化防止剤、粉体、香料、色剤、色素等を必要に応じて適宜配合することができる。
<Other optional components>
The cosmetic composition of the present invention contains other ingredients such as aqueous solvents, water-soluble polymers, surfactants, moisturizers, oils, UV absorbers, drugs, and chelating agents as long as the effects of the present invention are not impaired. , preservatives, pH adjusters, antioxidants, powders, fragrances, coloring agents, pigments, etc., can be appropriately blended as necessary.
 界面活性剤としては、ノニオン界面活性剤、カチオン界面活性剤、アニオン界面活性剤、両性界面活性剤より任意に選択することができる。 The surfactant can be arbitrarily selected from nonionic surfactants, cationic surfactants, anionic surfactants, and amphoteric surfactants.
 保湿剤としては、例えば、プロピレングリコール、ジプロピレングリコール、グリセリン、1,3-ブチレングリコール、コンドロイチン硫酸、ヒアルロン酸、ムコイチン硫酸、カロニン酸、アテロコラーゲン、コレステリル-12-ヒドロキシステアレート、乳酸ナトリウム、胆汁酸塩、Dl-ピロリドンカルボン酸塩、アルキレンオキシド誘導体、短鎖可溶性コラーゲン、ジグリセリン(EO)PO付加物等が挙げられる。なお、本明細書中、EOはエチレンオキシド、POはプロピレンオキシドを表す。 Examples of moisturizing agents include propylene glycol, dipropylene glycol, glycerin, 1,3-butylene glycol, chondroitin sulfate, hyaluronic acid, mucoitin sulfate, caronin acid, atelocollagen, cholesteryl-12-hydroxystearate, sodium lactate, and bile acid. salts, Dl-pyrrolidone carboxylates, alkylene oxide derivatives, short-chain soluble collagen, diglycerin (EO) PO adducts and the like. In this specification, EO represents ethylene oxide and PO represents propylene oxide.
 油分は、特に限定されるものではなく、化粧料に広く用いられている種々の油分を配合でき、固形油分、液状油分を問わない。 The oil is not particularly limited, and various oils widely used in cosmetics can be blended, regardless of whether they are solid or liquid.
 固形油分とは、一般に化粧料に用いられる室温において固体状又は半固体状の油分である。このような油分として、例えば、カカオ脂、ヤシ油、馬油、硬化ヤシ油、パーム油、牛脂、羊油、硬化牛脂、パーム核油、豚油、牛骨油、モクロウ核油、硬化油、牛脚脂、モクロウ、硬化ヒマシ油等の固体油脂;ミツロウ、キャンデリラロウ、綿ロウ、カルナウバロウ、ベイベリーロウ、イボタロウ、鯨ロウ、モンタンロウ、ヌカロウ、ラノリン、カポックロウ、酢酸ラノリン、サトウキビロウ、ラノリン脂肪酸イソプロピル、ラウリン酸ヘキシル、還元ラノリン、ホホバロウ、硬質ラノリン、セラックロウ、POEラノリンアルコールエーテル、POEラノリンアルコールアセテート、POEコレステロールエーテル、POE水素添加ラノリンアルコールエーテル等のロウ類;ポリエチレンワックス、パラフィンワックス、セレシン、ワセリン、マイクロクリスタリンワックス、ルナセラ等の炭化水素系ワックス;モノステアリルグリセリンエーテル(バチルアルコール)等の脂肪酸グリセリルエーテル;アセトグリセライド、トリ-2-ヘプチルウンデカン酸グリセライド等の脂肪酸グリセリド等が挙げられ、これらの1種または2種以上を組み合わせて使用することができる。 A solid oil is an oil that is solid or semi-solid at room temperature and is generally used in cosmetics. Examples of such oils include cacao butter, coconut oil, horse oil, hydrogenated coconut oil, palm oil, beef tallow, sheep oil, hydrogenated beef tallow, palm kernel oil, pork oil, beef bone oil, Japanese wax kernel oil, hydrogenated oil, Solid oils and fats such as beef leg fat, Japanese wax, hydrogenated castor oil; beeswax, candelilla wax, cotton wax, carnauba wax, bayberry wax, privet wax, whale wax, montan wax, bran wax, lanolin, kapok wax, lanolin acetate, sugarcane wax, lanolin fatty acid isopropyl, Waxes such as hexyl laurate, reduced lanolin, jojoba wax, hard lanolin, shellac wax, POE lanolin alcohol ether, POE lanolin alcohol acetate, POE cholesterol ether, POE hydrogenated lanolin alcohol ether; polyethylene wax, paraffin wax, ceresin, vaseline, micro Hydrocarbon waxes such as crystalline wax and lunasera; fatty acid glyceryl ethers such as monostearyl glycerin ether (bacyl alcohol); fatty acid glycerides such as acetoglyceride and tri-2-heptylundecanoic acid glyceride; Two or more kinds can be used in combination.
 液状油分とは、一般に化粧料に用いられる室温において液体の油分である。このような油分として、例えば、アボカド油、月見草油、ツバキ油、タートル油、マカデミアナッツ油、ヒマワリ油、アーモンド油、トウモロコシ油、ミンク油、オリーブ油、ナタネ油、卵黄油、ゴマ油、パーシック油、小麦胚芽油、サザンカ油、ヒマシ油、アマニ油、サフラワー油、綿実油、エノ油、大豆油、落花生油、茶実油、カヤ油、コメヌカ油、シナギリ油、日本キリ油、ホホバ油、胚芽油等の液体油脂;オクタン酸セチル、セチル2-エチルヘキサノエート、ジメチルオクタン酸ヘキシルデシル、エチルラウレート、ラウリン酸ヘキシル、ミリスチン酸イソプロピル、ミリスチン酸2-ヘキシルデシル、ミリスチン酸ミリスチル、ミリスチン酸オクチルドデシル、パルミチン酸イソプロピル、2-エチルヘキシルパルミテート、パルミチン酸2-ヘキシルデシル、パルミチン酸2-ヘプチルウンデシル、ステアリン酸ブチル、ステアリン酸イソセチル、イソステアリン酸イソセチル、オレイン酸デシル、ドデシルオレエート、オレイン酸オレイル、乳酸ミリスチル、乳酸セチル、リンゴ酸ジイソステアリル、12-ヒドロキシステアリル酸コレステリル、ヒマシ油脂肪酸メチルエステル、コハク酸2-エチルヘキシル、アジピン酸ジイソブチル、アジピン酸2-ヘキシルデシル、アジピン酸ジ-2-ヘプチルウンデシル、セバチン酸ジイソプロピル、セバチン酸ジ-2-エチルヘキシル、ジ-2-エチルヘキサン酸エチレングリコール、ジカプリン酸ネオペンチルグリコール、ジオクタン酸ネオペンチルグリコール、アセトグリセライド、ジ-2-ヘプチルウンデカン酸グリセリル、トリオクタン酸グリセリル、トリ-2-エチルヘキサン酸グリセリル、トリミリスチン酸グリセリル、トリイソパルミチン酸グリセリル、トリ-2-ヘプチルウンデカン酸グリセライド、トリ-2-エチルヘキサン酸トリメチロールプロパン、トリイソステアリン酸トリメチロールプロパン、テトラオクタン酸ペンタエリスリトール、テトラ-2-エチルヘキサン酸ペンタエリスリトール等のエステル油;流動パラフィン、スクワレン、プリスタン、ポリブテン等の炭化水素油;ジメチルポリシロキサン、メチルフェニルポリシロキサン、ジフェニルポリシロキサン等の鎖状ポリシロキサン、オクタメチルシクロテトラシロキサン、デカメチルシクロペンタシロキサン、ドデカメチルシクロヘキサンシロキサン等の環状ポリシロキサン、アミノ変性ポリシロキサン、ポリエーテル変性ポリシロキサン、アルキル変性ポリシロキサン、フッ素変性ポリシロキサン等の各種変性ポリシロキサン等のシリコーン油が挙げられ、これらの1種または2種以上を組み合わせて使用することができる。 A liquid oil is an oil that is liquid at room temperature and is generally used in cosmetics. Such oils include, for example, avocado oil, evening primrose oil, camellia oil, turtle oil, macadamia nut oil, sunflower oil, almond oil, corn oil, mink oil, olive oil, rapeseed oil, egg yolk oil, sesame oil, persic oil, and wheat germ. oil, sasanqua oil, castor oil, linseed oil, safflower oil, cottonseed oil, perilla oil, soybean oil, peanut oil, tea seed oil, kaya oil, rice bran oil, linagiri oil, Japanese paulownia oil, jojoba oil, germ oil, etc. Liquid fats and oils: cetyl octanoate, cetyl 2-ethylhexanoate, hexyldecyl dimethyloctanoate, ethyl laurate, hexyl laurate, isopropyl myristate, 2-hexyldecyl myristate, myristyl myristate, octyldodecyl myristate, palmitic acid Isopropyl acid, 2-ethylhexyl palmitate, 2-hexyldecyl palmitate, 2-heptylundecyl palmitate, butyl stearate, isocetyl stearate, isocetyl isostearate, decyl oleate, dodecyl oleate, oleyl oleate, myristyl lactate , cetyl lactate, diisostearyl malate, cholesteryl 12-hydroxystearate, castor oil fatty acid methyl ester, 2-ethylhexyl succinate, diisobutyl adipate, 2-hexyldecyl adipate, di-2-heptylundecyl adipate, diisopropyl sebacate, di-2-ethylhexyl sebacate, ethylene glycol di-2-ethylhexanoate, neopentyl glycol dicaprate, neopentyl glycol dioctanoate, acetoglyceride, glyceryl di-2-heptylundecanoate, glyceryl trioctanoate, Glyceryl tri-2-ethylhexanoate, glyceryl trimyristate, glyceryl triisopalmitate, glyceride tri-2-heptylundecanoate, trimethylolpropane tri-2-ethylhexanoate, trimethylolpropane triisostearate, tetraoctanoic acid ester oils such as pentaerythritol and pentaerythritol tetra-2-ethylhexanoate; hydrocarbon oils such as liquid paraffin, squalene, pristane and polybutene; chain polysiloxanes such as dimethylpolysiloxane, methylphenylpolysiloxane and diphenylpolysiloxane; Cyclic polysiloxanes such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexanesiloxane; various modified polysiloxanes such as amino-modified polysiloxane, polyether-modified polysiloxane, alkyl-modified polysiloxane, and fluorine-modified polysiloxane; Examples include silicone oils, and these can be used alone or in combination of two or more.
 紫外線吸収剤としては、パラアミノ安息香酸等の安息香酸系紫外線吸収剤;アントラニル酸メチル等のアントラニル酸系紫外線吸収剤;サリチル酸オクチル等のサリチル酸系紫外線吸収剤;パラメトキシケイ皮酸イソプロピル、パラメトキシケイ皮酸オクチル等のケイ皮酸系紫外線吸収剤;ジモルホリノピリダジノン等のピリダジン誘導体;4-メトキシ-4’-t-ブチルジベンゾイルメタン等のベンゾイルメタン誘導体;3-(4’-メチルベンジリデン)-D,l-カンファー、3-ベンジリデン-D,l-カンファー等のカンファー誘導体;2,2’-ヒドロキシ-5-メチルフェニルベンゾトリアゾール、2-(2’-ヒドロキシ-5’-t-オクチルフェニル)ベンゾトリアゾール、2-(2’-ヒドロキシ-5’-メチルフェニルベンゾトリアゾール等のベンゾトリアゾール誘導体;その他、2-フェニル-5-メチルベンゾキサゾール;ジベンザラジン;ジアニソイルメタン;5-(3,3-ジメチル-2-ノルボルニリデン)-3-ペンタン-2-オン等が挙げられる。 Examples of ultraviolet absorbers include benzoic acid-based ultraviolet absorbers such as para-aminobenzoic acid; anthranilic acid-based ultraviolet absorbers such as methyl anthranilate; salicylic acid-based ultraviolet absorbers such as octyl salicylate; Cinnamic acid UV absorbers such as octyl formate; pyridazine derivatives such as dimorpholinopyridazinone; benzoylmethane derivatives such as 4-methoxy-4'-t-butyldibenzoylmethane; 3-(4'-methylbenzylidene )-D,l-camphor, 3-benzylidene-D,l-camphor and other camphor derivatives; 2,2′-hydroxy-5-methylphenylbenzotriazole, 2-(2′-hydroxy-5′-t-octyl Benzotriazole derivatives such as phenyl)benzotriazole, 2-(2'-hydroxy-5'-methylphenylbenzotriazole; others, 2-phenyl-5-methylbenzoxazole; dibenzalazine; dianisoylmethane; 5-(3, 3-dimethyl-2-norbornylidene)-3-pentan-2-one and the like.
 薬剤としては、例えば、アスコルビン酸(ビタミンC)、トラネキサム酸、コウジ酸、エラグ酸、アルブチン、アルコキシサリチル酸、グリチルリチン酸、トコフェロール、レチノール及びこれらのまたは誘導体(例えば、L-アスコルビン酸ナトリウム、L-アスコルビン酸エステルマグネシウム塩、L-アスコルビン酸2-グルコシド(アルコルビルグルコシド)、2-O-エチル-L-アスコルビン酸、3-O-エチル-L-アスコルビン酸、4-メトキシサリチル酸ナトリウム塩、4-メトキシサリチル酸カリウム塩、グリチルリチン酸ジカリウム、グリチルリチン酸ステアリル、酢酸トコフェノール、酢酸レチノール、パルミチン酸レチノール等)等が挙げられる。 Drugs include, for example, ascorbic acid (vitamin C), tranexamic acid, kojic acid, ellagic acid, arbutin, alkoxysalicylic acid, glycyrrhizic acid, tocopherol, retinol and derivatives thereof (e.g. sodium L-ascorbate, L-ascorbic acid ester magnesium salt, L-ascorbic acid 2-glucoside (ascorbyl glucoside), 2-O-ethyl-L-ascorbic acid, 3-O-ethyl-L-ascorbic acid, 4-methoxysalicylic acid sodium salt, 4-methoxy potassium salicylate, dipotassium glycyrrhizinate, stearyl glycyrrhizinate, tocophenol acetate, retinol acetate, retinol palmitate, etc.).
 キレート剤としては、シトラマル酸、アガル酸、グリセリン酸、シキミ酸、ヒノキチオール、没食子酸、タンニン酸、コーヒー酸、エチレンジアミン四酢酸、エチレングリコールジアミン四酢酸、ジエチレントリアミン五酢酸、フィチン酸、ポリリン酸、メタリン酸、ならびにこれらの類似体、アルカリ金属塩およびカルボン酸エステル等が挙げられる。 Chelating agents include citramalic acid, agaric acid, glyceric acid, shikimic acid, hinokitiol, gallic acid, tannic acid, caffeic acid, ethylenediaminetetraacetic acid, ethyleneglycoldiaminetetraacetic acid, diethylenetriaminepentaacetic acid, phytic acid, polyphosphoric acid, and metaphosphoric acid. , and their analogues, alkali metal salts and carboxylic acid esters, and the like.
 防腐剤としては、メチルパラベン、エチルパラベン、ブチルパラベン等のパラオキシ安息香酸エステル類、安息香酸、サリチル酸、ソルビン酸、パラクロルメタクレゾール、ヘキサクロロフェン、塩化ベンザルコニウム、塩化クロルヘキシジン、トリクロロカルバニリド、感光素、フェノキシエタノール等が挙げられる。 Preservatives include paraoxybenzoic acid esters such as methylparaben, ethylparaben, and butylparaben, benzoic acid, salicylic acid, sorbic acid, parachlorometacresol, hexachlorophen, benzalkonium chloride, chlorhexidine chloride, trichlorocarbanilide, and photosensitizers. and phenoxyethanol.
 pH調整剤としては、例えば、乳酸-乳酸ナトリウム、クエン酸-クエン酸ナトリウム、コハク酸-コハク酸ナトリウム等の緩衝剤等が挙げられる。
 酸化防止剤としては、カロチノイド、ジブチルヒドロキシトルエン、ブチルヒドロキシアニソール、ピロ亜硫酸ナトリウム、没食子酸エステル類等が挙げられる。
Examples of pH adjusters include buffers such as lactic acid-sodium lactate, citric acid-sodium citrate, and succinic acid-sodium succinate.
Examples of antioxidants include carotenoids, dibutylhydroxytoluene, butylhydroxyanisole, sodium pyrosulfite, and gallic acid esters.
 本発明に係る化粧料は、医薬品、医薬部外品(軟膏剤等)、および洗顔料、化粧水、乳液、クリーム、ジェル、エッセンス(美容液)、パック、マスク等の基礎化粧品;ファンデーション、口紅等のメーキャップ化粧品;日焼け止め等のサンケア商品;芳香化粧品;ボディ化粧品等の形態に広く適用可能である。これらの形態は例示に過ぎず、本発明にかかる化粧料はこれらの形態に限定されるものではない。 Cosmetics according to the present invention include pharmaceuticals, quasi-drugs (ointments, etc.), and basic cosmetics such as facial cleansers, lotions, milky lotions, creams, gels, essences (beauty liquids), packs, and masks; foundations and lipsticks. sun care products such as sunscreen; aromatic cosmetics; body cosmetics, and the like. These forms are merely examples, and the cosmetic according to the present invention is not limited to these forms.
 以下に具体例を挙げて本発明をさらに詳細に説明するが、本発明は以下の実施例に限定されるものではない。また、以下の実施例における配合量は特に断らない限り、化粧料総量に対する質量%を示す。各実施例について具体的に説明する前に、採用した評価方法および分子量測定方法について説明する。 The present invention will be described in more detail with specific examples below, but the present invention is not limited to the following examples. In addition, unless otherwise specified, the blending amounts in the following examples are shown in % by mass with respect to the total amount of the cosmetic. Before describing each example in detail, the employed evaluation method and molecular weight measurement method will be described.
<使用性の評価>
 専門パネル10名が顔面に試料を塗布し、使用性(塗布中の肌へのなじみのはやさ、塗布中のぬるつきのなさ、塗布中のみずみずしさ、塗布後の肌のべたつきのなさ、塗布後の肌のしっとりさ)について評価した。各専門パネルの評価をもとに、以下の基準に従って試料を判定した。
<Usability evaluation>
A panel of 10 specialists applied the sample to the face and evaluated usability (quickness of familiarity with the skin during application, lack of sliminess during application, freshness during application, non-stickiness of skin after application, after application). Moistness of the skin) was evaluated. Based on the evaluation by each expert panel, the samples were judged according to the following criteria.
(1)塗布中の肌へのなじみのはやさ
AA:パネル10名中9名以上が肌のなじみがはやいと回答した。
A:パネル10名中7名以上9名未満が肌のなじみがはやいと回答した。
B:パネル10名中5名以上7名未満が肌のなじみがはやいと回答した。
C:パネル10名中3名以上5名未満が肌のなじみがはやいと回答した。
D:パネル10名中1名以上3名未満が肌のなじみがはやいと回答した。
E:パネル10名全員が肌のなじみのはやさに欠けると回答した。
(1) Absorbability into the skin during application AA: More than 9 out of 10 panelists answered that the absorbability into the skin was rapid.
A: 7 or more but less than 9 out of 10 panelists answered that the skin felt quickly.
B: 5 or more but less than 7 panelists out of 10 panelists answered that the product blended quickly with the skin.
C: 3 or more but less than 5 out of 10 panelists answered that the skin felt quickly.
D: 1 or more but less than 3 out of 10 panelists answered that the skin felt quickly.
E: All 10 panelists answered that it lacked quickness in skin compatibility.
(2)塗布中のぬるつきのなさ
AA:パネル10名中9名以上がぬるつきがないと回答した。
A:パネル10名中7名以上9名未満がぬるつきがないと回答した。
B:パネル10名中5名以上7名未満がぬるつきがないと回答した。
C:パネル10名中3名以上5名未満がぬるつきがないと回答した。
D:パネル10名中1名以上3名未満がぬるつきがないと回答した。
E:パネル10名全員がぬるつきがあると回答した。
(2) Absence of sliminess during application AA: More than 9 out of 10 panelists answered that there was no sliminess.
A: 7 or more and less than 9 out of 10 panelists answered that there was no sliminess.
B: 5 or more but less than 7 out of 10 panelists answered that there was no sliminess.
C: 3 or more and less than 5 out of 10 panelists answered that there was no sliminess.
D: 1 or more but less than 3 out of 10 panelists answered that there was no sliminess.
E: All 10 panelists answered that there was sliminess.
(3)塗布中のみずみずしさ
AA:パネル10名中9名以上がみずみずしい感触があると回答した。
A:パネル10名中7名以上9名未満がみずみずしい感触があると回答した。
B:パネル10名中5名以上7名未満がみずみずしい感触があると回答した。
C:パネル10名中3名以上5名未満がみずみずしい感触があると回答した。
D:パネル10名中1名以上3名未満がみずみずしい感触があると回答した。
E:パネル10名全員がみずみずしい感触に欠けると回答した。
(3) Fresh feeling during application AA: More than 9 out of 10 panelists answered that they felt a fresh feeling.
A: 7 or more but less than 9 out of 10 panelists answered that they had a fresh feeling.
B: 5 or more but less than 7 out of 10 panelists answered that they had a fresh feeling.
C: 3 or more but less than 5 out of 10 panelists answered that they had a fresh touch.
D: 1 or more but less than 3 out of 10 panelists answered that they had a fresh feeling.
E: All 10 panelists answered that it lacked a fresh feel.
(4)塗布後の肌のべたつきのなさ
AA:パネル10名中9名以上がべたつきがないと回答した。
A:パネル10名中7名以上9名未満がべたつきがないと回答した。
B:パネル10名中5名以上7名未満がべたつきがないと回答した。
C:パネル10名中3名以上5名未満がべたつきがないと回答した。
D:パネル10名中1名以上3名未満がべたつきがないと回答した。
E:パネル10名全員がべたつきがあると回答した。
(4) Absence of skin stickiness after application AA: More than 9 out of 10 panelists answered that there was no stickiness.
A: 7 or more and less than 9 out of 10 panelists answered that there was no stickiness.
B: 5 or more and less than 7 panelists out of 10 panelists answered that there was no stickiness.
C: 3 or more and less than 5 out of 10 panelists answered that there was no stickiness.
D: 1 or more but less than 3 out of 10 panelists answered that there was no stickiness.
E: All 10 panelists answered that there was stickiness.
(5)塗布後の肌のしっとりさ
AA:パネル10名中9名以上が肌のしっとりさがあると回答した。
A:パネル10名中7名以上9名未満が肌のしっとりさがあると回答した。
B:パネル10名中5名以上7名未満が肌のしっとりさがあると回答した。
C:パネル10名中3名以上5名未満が肌のしっとりさがあると回答した。
D:パネル10名中1名以上3名未満が肌のしっとりさがあると回答した。
E:パネル10名全員が肌のしっとりさに欠けると回答した。
(5) Moistness of the skin after application AA: More than 9 out of 10 panelists answered that the skin was moist.
A: 7 or more but less than 9 out of 10 panelists answered that the skin was moist.
B: 5 or more but less than 7 out of 10 panelists answered that the skin was moist.
C: 3 or more but less than 5 out of 10 panelists answered that the skin was moist.
D: 1 or more but less than 3 out of 10 panelists answered that the skin was moist.
E: All 10 panelists answered that the skin lacked moisture.
<分子量測定>
 使用したポリアクリル酸ナトリウムの分子量は、以下の条件でGPC解析を行うことにより測定した。
ガードカラム:ショーデックス OHpak SB-G、1本(昭和電工(株)社製)、カラム:ショーデックス OHpak SB-804HQ、2本(昭和電工(株)社製)、
カラム温度:40℃、
カラムオーブン:CTO-10ASVP(島津製作所)、
脱気装置:ERC-3215α(イー・アール・シー(株)社製)、
ポンプ:DP-8020デュアルポンプ(東ソー(株)社製)、
屈折率検出器:RI-8020示差屈折計(東ソー(株)社製)、
溶離溶媒:5mM リン酸緩衝液(pH 8.0)+90%アセトニトリル
流速:0.6ml/分、
注入量:10μl、
分子量スタンダード:標準ポリスチレンスルホン酸ナトリウム。
<Molecular weight measurement>
The molecular weight of sodium polyacrylate used was measured by GPC analysis under the following conditions.
Guard column: Shodex OHpak SB-G, 1 (manufactured by Showa Denko KK), Column: Shodex OHpak SB-804HQ, 2 (manufactured by Showa Denko KK),
Column temperature: 40°C,
Column oven: CTO-10ASVP (Shimadzu Corporation),
Degassing device: ERC-3215α (manufactured by ERC Co., Ltd.),
Pump: DP-8020 dual pump (manufactured by Tosoh Corporation),
Refractive index detector: RI-8020 differential refractometer (manufactured by Tosoh Corporation),
Elution solvent: 5 mM phosphate buffer (pH 8.0) + 90% acetonitrile Flow rate: 0.6 ml/min,
Injection volume: 10 μl,
Molecular Weight Standards: standard sodium polystyrene sulfonate.
[実施例1~15および比較例1~3]
 表1および表2に示される配合で、実施例1~15および比較例1~3の化粧料を常法により調製し、上記の項目(1)~(5)について評価した。
Figure JPOXMLDOC01-appb-T000005
Figure JPOXMLDOC01-appb-T000006
*1:重量平均分子量が200万であり、分子量が1000万以上の巨大分子の含有量が10質量%以下であるポリアクリル酸ナトリウム
*2:アロンビス(登録商標)SX(東亜合成株式会社製)
[Examples 1 to 15 and Comparative Examples 1 to 3]
Cosmetics of Examples 1 to 15 and Comparative Examples 1 to 3 were prepared by a conventional method with formulations shown in Tables 1 and 2, and evaluated for the above items (1) to (5).
Figure JPOXMLDOC01-appb-T000005
Figure JPOXMLDOC01-appb-T000006
* 1: Sodium polyacrylate having a weight average molecular weight of 2 million and a content of macromolecules with a molecular weight of 10 million or more is 10% by mass or less * 2: Aronbis (registered trademark) SX (manufactured by Toagosei Co., Ltd.)
 表1および表2に示されるように、重量平均分子量が400万~500万であって、分子量が1000万以上の巨大分子を10質量%より多く含むポリアクリル酸ナトリウム(アロンビス(登録商標)SX)を配合した化粧料では、全ての評価項目で評価結果が悪化した(比較例1)。 As shown in Tables 1 and 2, sodium polyacrylate (Aronbis (registered trademark) SX ), the evaluation results were worse in all evaluation items (Comparative Example 1).
 一方、重量平均分子量が200万であり、分子量が1000万以上の巨大分子の含有量が10質量%以下となるように分子量分布が制御されたポリアクリル酸ナトリウムを配合すると、全ての評価項目について優れた結果が得られた。また、ジグリセリン、糖アルコール、またはポリエチレングリコールをさらに配合することにより、使用感がより向上することが確認された。 On the other hand, when sodium polyacrylate with a weight average molecular weight of 2 million and a molecular weight distribution controlled so that the content of macromolecules with a molecular weight of 10 million or more is 10% by mass or less, all the evaluation items Excellent results were obtained. In addition, it was confirmed that the addition of diglycerin, sugar alcohol, or polyethylene glycol further improved the feeling of use.
 さらに、1-(2-ヒドロキシエチル)-2-イミダゾリジノンに代えて、べたつきを生じることが知られているアスコルビルグルコシドを配合してみたところ、全ての評価項目で十分な効果を得られなかった(比較例2および3)。このことから、ポリアクリル酸またはその塩によるべたつき等の改善効果は1-(2-ヒドロキシエチル)-2-イミダゾリジノンに対して特異的に発現されるものと考えられる。 Furthermore, when ascorbyl glucoside, which is known to cause stickiness, was added instead of 1-(2-hydroxyethyl)-2-imidazolidinone, sufficient effects were not obtained in all evaluation items. (Comparative Examples 2 and 3). From this, it is considered that the effect of improving stickiness and the like by polyacrylic acid or a salt thereof is specifically exhibited for 1-(2-hydroxyethyl)-2-imidazolidinone.

Claims (8)

  1. (A)式(1)で表される環状カルボキサミド誘導体またはその塩
    Figure JPOXMLDOC01-appb-C000001
    (式中、
     Rは、水酸基で置換されていてもよい炭素数1~6の炭化水素基、または水素原子であり、
     Xは、-CH-または-N(R)-であり、ここで、Rは、水酸基で置換されていてもよい炭素数1~6の炭化水素基、または水素原子であり、かつ
     nは、1~3の整数である)、および
    (B)重量平均分子量が50万~800万であり、分子量が1000万以上である化合物の含有量が10質量%以下であるポリアクリル酸またはその塩
    を含んでなる、化粧料。
    (A) a cyclic carboxamide derivative represented by formula (1) or a salt thereof
    Figure JPOXMLDOC01-appb-C000001
    (In the formula,
    R 1 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom,
    X is —CH 2 — or —N(R 2 )—, wherein R 2 is a hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, or a hydrogen atom, and n is an integer of 1 to 3), and (B) a polyacrylic acid having a weight average molecular weight of 500,000 to 8,000,000 and a content of a compound having a molecular weight of 10,000,000 or more is 10% by mass or less, or Cosmetics containing the salt.
  2.  (A)成分の式(1)において、
     Rが、炭素数1~3のヒドロキシアルキル基であり、
     Xが、-CH-または-NH-であり、かつ
     nが、1である、請求項1に記載の化粧料。
    (A) In the formula (1) of the component,
    R 1 is a hydroxyalkyl group having 1 to 3 carbon atoms,
    2. The cosmetic according to claim 1, wherein X is -CH 2 - or -NH-, and n is 1.
  3.  (A)成分が、1-(2-ヒドロキシエチル)-2-イミダゾリジノンである、請求項1または2に記載の化粧料。 The cosmetic according to claim 1 or 2, wherein the component (A) is 1-(2-hydroxyethyl)-2-imidazolidinone.
  4.  (A)成分の配合量が、化粧料の総量に対して、0.05~7質量%である、請求項1または2に記載の化粧料。 The cosmetic according to claim 1 or 2, wherein the blending amount of component (A) is 0.05 to 7% by mass with respect to the total amount of the cosmetic.
  5.  (B)成分の配合量が、化粧料の総量に対して、0.001~0.5質量%である、請求項1または2に記載の化粧料。 The cosmetic according to claim 1 or 2, wherein the blending amount of component (B) is 0.001 to 0.5% by mass with respect to the total amount of the cosmetic.
  6.  (C)ジグリセリンをさらに含んでなる、請求項1または2に記載の化粧料。 (C) The cosmetic according to claim 1 or 2, further comprising diglycerin.
  7.  (D)マンニトール、キシリトール、エリスリトール、ソルビトール、マルチトール、およびイノシトールからなる群から選択される糖アルコールをさらに含む、請求項1または2に記載の化粧料。 (D) The cosmetic according to claim 1 or 2, further comprising a sugar alcohol selected from the group consisting of mannitol, xylitol, erythritol, sorbitol, maltitol, and inositol.
  8.  (E)ポリエチレングリコールをさらに含んでなる、請求項1または2に記載の化粧料。 (E) The cosmetic according to claim 1 or 2, further comprising polyethylene glycol.
PCT/JP2022/036654 2021-10-13 2022-09-30 Cosmetic WO2023063106A1 (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014125432A (en) * 2012-12-25 2014-07-07 Lion Corp Skin patch composition
WO2015052804A1 (en) * 2013-10-09 2015-04-16 株式会社 資生堂 Low-stringiness thickener and cosmetic material admixed with said thickener
JP2020176085A (en) * 2019-04-17 2020-10-29 ポーラ化成工業株式会社 Wrinkle ameliorating composition
JP2020180103A (en) * 2019-04-26 2020-11-05 ポーラ化成工業株式会社 Wrinkle-improving composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014125432A (en) * 2012-12-25 2014-07-07 Lion Corp Skin patch composition
WO2015052804A1 (en) * 2013-10-09 2015-04-16 株式会社 資生堂 Low-stringiness thickener and cosmetic material admixed with said thickener
JP2020176085A (en) * 2019-04-17 2020-10-29 ポーラ化成工業株式会社 Wrinkle ameliorating composition
JP2020180103A (en) * 2019-04-26 2020-11-05 ポーラ化成工業株式会社 Wrinkle-improving composition

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