WO2023063106A1 - Produit cosmétique - Google Patents

Produit cosmétique 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
Authority
WO
WIPO (PCT)
Prior art keywords
acid
cosmetic
oil
molecular weight
component
Prior art date
Application number
PCT/JP2022/036654
Other languages
English (en)
Japanese (ja)
Inventor
友香 水野
育浩 鈴木
Original Assignee
株式会社 資生堂
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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/zh
Publication of WO2023063106A1 publication Critical patent/WO2023063106A1/fr

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Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin

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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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)

Abstract

Le problème décrit par la présente invention est de fournir un produit cosmétique présentant une excellente sensation après usage. La solution selon la présente invention porte sur un produit cosmétique comprenant : (A) un dérivé de carboxamide cyclique présentant une structure spécifique, ou un sel de celui-ci ; et (B) un acide polyacrylique présentant une polydispersité contrôlée, ou un sel de celui-ci.
PCT/JP2022/036654 2021-10-13 2022-09-30 Produit cosmétique WO2023063106A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202280061802.6A CN117999060A (zh) 2021-10-13 2022-09-30 化妆品

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2021-168399 2021-10-13
JP2021168399 2021-10-13

Publications (1)

Publication Number Publication Date
WO2023063106A1 true WO2023063106A1 (fr) 2023-04-20

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ID=85988313

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2022/036654 WO2023063106A1 (fr) 2021-10-13 2022-09-30 Produit cosmétique

Country Status (2)

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CN (1) CN117999060A (fr)
WO (1) WO2023063106A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014125432A (ja) * 2012-12-25 2014-07-07 Lion Corp 皮膚貼付剤組成物
WO2015052804A1 (fr) * 2013-10-09 2015-04-16 株式会社 資生堂 Épaississant à faible pouvoir filant et substance cosmétique mélangée avec ledit épaississant
JP2020176085A (ja) * 2019-04-17 2020-10-29 ポーラ化成工業株式会社 シワ改善用組成物
JP2020180103A (ja) * 2019-04-26 2020-11-05 ポーラ化成工業株式会社 シワ改善用組成物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014125432A (ja) * 2012-12-25 2014-07-07 Lion Corp 皮膚貼付剤組成物
WO2015052804A1 (fr) * 2013-10-09 2015-04-16 株式会社 資生堂 Épaississant à faible pouvoir filant et substance cosmétique mélangée avec ledit épaississant
JP2020176085A (ja) * 2019-04-17 2020-10-29 ポーラ化成工業株式会社 シワ改善用組成物
JP2020180103A (ja) * 2019-04-26 2020-11-05 ポーラ化成工業株式会社 シワ改善用組成物

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Publication number Publication date
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