Cosmetic

A cosmetic formulation with polyglycerol fatty acid ester and pyrimidylpyrazole compound or its salt, combined with water, addresses stickiness and enhances smoothness, ensuring a non-sticky and smooth application.

JP2026003399APending Publication Date: 2026-01-13SHISEIDO CO LTD
View PDF 1 Cites 0 Cited by

Patent Information

Application Number
JP2024101328
Authority / Receiving Office
JP · JP
Patent Type
Applications
Current Assignee / Owner
Filing Date
2024-06-24
Publication Date
2026-01-13

AI Technical Summary

Technical Problem

Cosmetics containing pyrimidylpyrazole compounds often cause stickiness and lack a smooth feel upon application.

Method used

A cosmetic formulation comprising a polyglycerol fatty acid ester, a pyrimidylpyrazole compound or its salt, and water, which balances hydrophilicity and lipophilicity to form vesicles that encapsulate ingredients, providing a smooth and non-sticky application.

Benefits of technology

The formulation achieves a smooth and non-sticky application experience by suppressing stickiness while maintaining the whitening effects of pyrimidylpyrazole compounds.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure 2026003399000001
    Figure 2026003399000001
  • Figure 2026003399000002
    Figure 2026003399000002
  • Figure 2026003399000003
    Figure 2026003399000003
Patent Text Reader

Abstract

To provide a cosmetic excellent in feeling of use.SOLUTION: The cosmetic comprises (A) a polyglycerol fatty acid ester, (B) a pyrimidylpyrazole compound having a specific structure or its salt, and (C) water.SELECTED DRAWING: None
Need to check novelty before this filing date? Find Prior Art

Description

[Technical Field]

[0001] The present invention relates to a cosmetic preparation. Specifically, the present invention relates to a cosmetic preparation comprising a pyrimidylpyrazole compound or a salt thereof. [Background technology]

[0002] Pigmentation such as age spots and freckles on the skin occurs when hormonal abnormalities or ultraviolet light stimulate the skin, resulting in increased melanin production in epidermal pigment cells and excessive melanin deposition in the epidermis. To prevent or improve this abnormal deposition of melanin, whitening agents are incorporated into cosmetics. Various ingredients are known to be incorporated as whitening agents, and in recent years, pyrimidylpyrazole compounds have also been known as useful whitening agents (e.g., Patent Document 1). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2009 / 099192 Summary of the Invention

[0004] According to the studies of the present inventors, it has been found that when a pyrimidylpyrazole compound is used in a cosmetic, it tends to cause stickiness after application. In addition, a smooth feel in use is generally required for a cosmetic. The present inventors have surprisingly found that a cosmetic containing a pyrimidylpyrazole compound or its salt and a polyglycerol fatty acid ester can suppress stickiness and provide a smooth feel in use. The present invention is based on these findings.

[0005] According to the present disclosure, the following inventions are provided. [1] (A) a polyglycerol fatty acid ester, (B) a pyrimidylpyrazole compound represented by formula (1) or a salt thereof, and (C) water, A cosmetic comprising: [ka] (In the formula, R 1 , R 3 , R 4 and R 6 are each independently, C 1-3 is an alkyl group, and R 2 and R 5 are each independently a hydrogen atom or C 1-3 alkyl group) [2]R 2 and R 5 [1] The cosmetic according to [1], wherein is a hydrogen atom. [3]R 1 , R 3 , R 4 and R 6 The cosmetic according to [1] or [2], wherein is a methyl group. [4] The cosmetic preparation according to any one of [1] to [3], wherein the number of carbon atoms in the fatty acid moiety of the polyglycerin fatty acid ester is 12 or more and 17 or less. [5] The cosmetic preparation according to any one of [1] to [4], wherein the polyglycerin moiety in the polyglycerin fatty acid ester is a dimer or more and a decamer or less. [6] The cosmetic preparation according to any one of [1] to [5], wherein component (A) is polyglyceryl-6 laurate or polyglyceryl-6 myristate. [7] The cosmetic according to any one of [1] to [6], wherein the content of component (A) is 0.1 mass % or more and 10 mass % or less relative to the total amount of the cosmetic. [8] The cosmetic according to any one of [1] to [7], wherein the content of component (B) is 0.01 mass % or more and 1.5 mass % or less relative to the total amount of the cosmetic. [9] (D) The cosmetic according to any one of [1] to [8], wherein the oil content is 0% by mass or more and 40% by mass or less relative to the total amount of the cosmetic.

[10] The cosmetic according to any one of [1] to [9], which is an aqueous cosmetic or an oil-in-water emulsion cosmetic.

[0006] According to the present invention, it is possible to provide a cosmetic product that has an excellent feeling when used. In particular, it is possible to provide a cosmetic product that has a smooth feeling when applied and that is less sticky after application.

[0007] The present invention relates to a cosmetic comprising (A) a polyglycerol fatty acid ester, (B) a pyrimidylpyrazole compound having a specific structure or a salt thereof, and (C) water.

[0008] (A) Polyglycerol fatty acid ester Polyglycerol fatty acid esters can be prepared by esterifying fatty acids with polyglycerol. Here, in the polyglycerol fatty acid esters, the portion derived from the fatty acid is referred to as the fatty acid portion, and the portion derived from the polyglycerol is referred to as the polyglycerol portion. The fatty acid portion has lipophilicity, and the polyglycerol portion has hydrophilicity. The polyglycerol fatty acid esters may form vesicles, which are bilayer membrane-occluded bodies encapsulating other ingredients in cosmetics. The bilayer membrane of the vesicle can retain oil.

[0009] The number of carbon atoms in the fatty acid moiety of the polyglycerol fatty acid ester is preferably 12 or more, 13 or more, or 14 or more, and preferably 17 or less, 16 or less, or 15 or less. The fatty acid may be a saturated fatty acid or an unsaturated fatty acid, and may be a straight-chain fatty acid or a branched-chain fatty acid. Examples of such fatty acids include lauric acid, myristic acid, and palmitic acid. The fatty acid is preferably lauric acid or myristic acid.

[0010] The polyglycerol moiety of the polyglycerol fatty acid ester is preferably a dimer or more, a trimer or more, or a tetramer or more, and is preferably a decamer or less, a nonamer or less, an octamer or less, a heptamer or less, or a hexamer or less.

[0011] The OH / C ratio of the polyglycerol fatty acid ester is preferably 0.20 or more, 0.25 or more, 0.30 or more, 0.35 or more, 0.40 or more, 0.45 or more, or 0.50 or more, and is preferably 0.80 or less, 0.75 or less, 0.70 or less, 0.65 or less, or 0.60 or less. Polyglycerol fatty acid esters having such an OH / C ratio are preferred because they can improve the oil-solubilizing ability of vesicles when they are formed.

[0012] Here, in the present disclosure, "OH / C ratio" refers to the ratio of the number of hydroxyl groups in the polyglycerol moiety to the number of carbon atoms in the fatty acid moiety. The OH / C ratio is also a parameter relating to the balance between hydrophilicity and lipophilicity. As an example, in the case of polyglyceryl-6 laurate, the number of carbon atoms in the fatty acid moiety is 12. Furthermore, the polyglycerol moiety is a hexamer, and the number of hydroxyl groups in this case is 7 (=6+1). Therefore, the OH / C ratio of polyglyceryl-6 laurate is 0.58 (=7 / 12). Furthermore, in the case of polyglyceryl-6 myristate, the number of carbon atoms in the fatty acid moiety is 14. Furthermore, the polyglycerol moiety is a hexamer, and the number of hydroxyl groups in this case is 7 (=6+1). Therefore, the OH / C ratio of polyglyceryl-6 laurate is 0.50 (=7 / 14).

[0013] The polyglycerol fatty acid ester is preferably a polyglycerol mono-fatty acid ester. Specific examples of the polyglycerol fatty acid ester include polyglyceryl-6 myristate, polyglyceryl-2 laurate, polyglyceryl-4 laurate, polyglyceryl-5 laurate, polyglyceryl-6 laurate, and polyglyceryl-10 palmitate. The polyglycerol fatty acid ester is preferably polyglyceryl-6 laurate or glyceryl-6 myristate.

[0014] The content of (A) polyglycerol fatty acid ester can be 0.1 mass% or more, 0.2 mass% or more, or 0.3 mass% or more, relative to the total amount of the cosmetic, and can be 10 mass% or less, 5.0 mass% or less, or 3.0 mass% or less.

[0015] Generally, the higher the content of component (B), the more likely the cosmetic composition is to become sticky. However, by including component (A), the cosmetic composition of the present invention can suppress stickiness even when the content of component (B) is high.

[0016] (B) a pyrimidylpyrazole compound or a salt thereof The cosmetic according to the present invention comprises (B) a pyrimidylpyrazole compound represented by formula (1) or a salt thereof. [ka] During the ceremony, R 1 , R 3 , R 4 and R 6 are each independently, C 1-3 It is an alkyl group, specifically a methyl group, an ethyl group, an n-propyl group, an isopropyl group, or a cyclopropyl group, preferably a methyl group or an ethyl group, more preferably a methyl group. R 2 and R 5 are each independently a hydrogen atom or C 1-3 It is an alkyl group, specifically a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, or a cyclopropyl group, preferably a hydrogen atom, a methyl group, or an ethyl group, more preferably a hydrogen atom.

[0017] Component (B) may be a salt of the pyrimidylpyrazole compound represented by formula (1). The type of salt is not particularly limited as long as it is pharmaceutically acceptable, and may be an inorganic salt or an organic salt. Examples of salts include hydrochloride, hydrobromide, sulfate, phosphate, acetate, propionate, citrate, lactate, oxalate, maleate, fumarate, tartrate, and methanesulfonate. Component (B) is preferably dimethylpyrazolyldimethylpyrimidine hydrochloride.

[0018] The content of component (B) can be 0.01 mass% or more, 0.05 mass% or more, or 0.1 mass% or more, relative to the total amount of the cosmetic, and can be 1.5 mass% or less, 1.2 mass% or less, or 1.0 mass% or less.

[0019] (C)Water The cosmetic according to the present invention comprises (C) water. The water used in cosmetics, quasi-drugs, etc. can be used, such as purified water, ion-exchanged water, tap water, etc. The water content is preferably 40% by mass or more, or 50% by mass or more, and preferably 95% by mass or less, or 90% by mass or less, based on the total amount of the cosmetic according to the present invention.

[0020] (D) Oil The cosmetic of the present invention may contain (D) an oil component in addition to (A) to (C). In such cases, the cosmetic of the present invention generally takes the form of an oil-in-water cosmetic or a water-in-oil cosmetic, but may also be, for example, a two-layer cosmetic that separates into two layers upon standing.

[0021] Examples of (D) oils include ester oils, silicone oils, hydrocarbon oils, higher fatty acids, higher alcohols, liquid oils, solid oils, and semi-solid oils. The oils are preferably ester oils, silicone oils, hydrocarbon oils, and higher alcohols. One or more types of (D) component can be blended. When the cosmetic is an oil-in-water emulsion cosmetic, the content of (D) component is preferably 0.5% by mass or more, or 1% by mass or more, and preferably 40% by mass or less, or 30% by mass or less, relative to the total amount of the cosmetic. When the cosmetic is an aqueous cosmetic, the content of (D) component is preferably 0% by mass or more, or 1% by mass or less.

[0022] Examples of ester oils include octyl octanoate, nonyl nonanoate, cetyl octanoate, isopropyl myristate, octyldodecyl myristate, isopropyl palmitate, ethylhexyl palmitate, butyl stearate, hexyl laurate, myristyl myristate, decyl oleate, hexyldecyl dimethyloctanoate, cetyl lactate, myristyl lactate, lanolin acetate, isocetyl stearate, isocetyl isostearate, 12-hydroxystearate, hydroxypropyl methyl ... Cholesteryl tearic acid, ethylene glycol di-2-ethylhexanoate, dipentaerythritol fatty acid ester, N-alkyl glycol monoisostearate, neopentyl glycol dicaprate, tripropylene glycol pivalate, diisostearyl malate, glyceryl di-2-heptylundecanoate, glyceryl diisostearate, trimethylolpropane tri-2-ethylhexanoate, trimethylolpropane triisostearate, tetra-2 -Pentaerythritol ethylhexanoate, glyceryl tri-2-ethylhexanoate, glyceryl trioctanoate, glyceryl triisopalmitate, trimethylolpropane triisostearate, cetyl 2-ethylhexanoate-2-ethylhexyl palmitate, glyceryl trimyristate, tri-2-heptylundecanoic acid glyceride, castor oil fatty acid methyl ester, oleyl oleate, acetoglyceride, 2-heptylundecyl palmitate, Examples of suitable oleic acid surfactants include diisobutyl adipate, N-lauroyl-L-glutamic acid 2-octyldodecyl ester, di-2-heptylundecyl adipate, ethyl laurate, di-2-ethylhexyl sebacate, 2-hexyldecyl myristate, 2-hexyldecyl palmitate, 2-hexyldecyl adipate, diisopropyl sebacate, 2-ethylhexyl succinate, triethyl citrate, cetyl ethylhexanoate, and macadamia nut fatty acid phytosteryl.

[0023] Examples of silicone oils include linear polysiloxanes (e.g., dimethicone, diphenylsiloxyphenyltrimethicone, diphenylpolysiloxane, etc.), cyclic polysiloxanes (e.g., octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, etc.), silicone resins that form a three-dimensional network structure, silicone rubber, various modified polysiloxanes (amino-modified polysiloxane, polyether-modified polysiloxane, alkyl-modified polysiloxane, fluorine-modified polysiloxane, etc.), and acrylic silicones, with linear polysiloxanes being preferred.

[0024] Examples of hydrocarbon oils include isododecane, isohexadecane, isoparaffin, mineral oil (liquid paraffin), ozokerite, squalane, pristane, paraffin, ceresin, squalene, petrolatum, microcrystalline wax, and hydrogenated polydecene.

[0025] Examples of higher fatty acids include lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, undecylenic acid, tall acid, isostearic acid, linoleic acid, linolenic acid, eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA).

[0026] Examples of higher alcohols include straight-chain alcohols (e.g., lauryl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, myristyl alcohol, oleyl alcohol, cetostearyl alcohol, etc.), branched-chain alcohols (e.g., lanolin alcohol, cholesterol, phytosterol, hexyldodecanol, isostearyl alcohol, octyldodecanol, etc.), and the like.

[0027] Examples of liquid oils include avocado oil, camellia oil, macadamia nut oil, corn oil, olive oil, rapeseed oil, sesame oil, persic oil, wheat germ oil, camellia oil, castor oil, linseed oil, safflower oil, cottonseed oil, perilla oil, soybean oil, peanut oil, tea seed oil, kaya oil, rice bran oil, Chinese tung oil, Japanese tung oil, jojoba oil, germ oil, triglycerin, etc. Examples of solid oils include cocoa butter, coconut oil, hydrogenated coconut oil, palm oil, palm kernel oil, hydrogenated palm oil, Japan wax kernel oil, hydrogenated oil, Japan wax, hydrogenated castor oil, etc. Examples of semi-solid oils include shea butter, partially hydrogenated coconut oil, partially hydrogenated jojoba oil, etc.

[0028] The cosmetic of the present invention may further contain a polyhydric alcohol. Examples of polyhydric alcohols include glycerin, ethylene glycol, propylene glycol, 1,3-butylene glycol, dipropylene glycol, polyethylene glycol, polypropylene glycol, and polybutylene glycol. Among these, dipropylene glycol or 1,3-butylene glycol is preferred. Polyhydric alcohols can be used alone or in combination. While not limited thereto, the polyhydric alcohol content is preferably 1% by mass or more, 2% by mass or more, or 5% by mass or more, and preferably 30% by mass or less, 25% by mass or less, or 20% by mass or less, based on the total amount of the cosmetic.

[0029] The cosmetic of the present invention may further contain a thickener. As a thickener, (i) Water-soluble thickeners, for example, plant-based polymers such as gum arabic, tragacanth gum, galactan, carob gum, guar gum, karaya gum, carrageenan, pectin, agar, quince seed (quince), and algae colloid (brown algae extract); microbial polymers such as dextran, succinoglucan, pullulan, and xanthan gum; animal-based polymers such as collagen, casein, albumin, and gelatin; cellulose-based polymers such as methylcellulose, nitrocellulose, ethylcellulose, methylhydroxypropylcellulose, hydroxyethylcellulose, sodium cellulose sulfate, hydroxypropylcellulose, sodium carboxymethylcellulose, crystalline cellulose, and cellulose powder; alginic acid-based polymers such as sodium alginate and propylene glycol alginate; vinyl-based polymers such as polyvinyl alcohol, polyvinyl methyl ether, polyvinylpyrrolidone, and carboxyvinyl polymer (carbomer); polyoxyethylene-based polymers such as hydrophobically modified polyether urethane; acrylic polymers such as sodium polyacrylate, polyethyl acrylate, and polyacrylamide; polyethyleneimine; cationic polymers, (ii) Inorganic water-soluble polymers, such as bentonite, magnesium aluminum silicate, laponite, hectorite, and silicic anhydride. The thickeners may be used alone or in combination of two or more.

[0030] The content of the thickener is preferably 0.01 mass % or more, 0.05 mass % or more, or 0.1 mass % or more, and preferably 1.5 mass % or less, 1.0 mass % or less, or 0.8 mass % or less, relative to the total amount of the cosmetic.

[0031] The cosmetic of the present invention may further contain a surfactant. The type of surfactant is not limited, but it is preferable that the cosmetic of the present invention contains an anionic surfactant.

[0032] As anionic surfactant, for example, N-acylamino acid salt and N-acylmethyl taurine salt can be mentioned.Specifically, for example, N-acyl glutamate salt such as potassium cocoyl glutamate, N-acyl-N-methyl-β-alanine salt, N-acyl sarcosinate salt, sodium N-cocoyl taurine, sodium N-cocoyl-N-methyl taurine, sodium N-lauroyl-N-methyl taurine, sodium N-stearoyl-N-methyl taurine, sodium N-coconut oil fatty acid-N-methyl taurine, triethanolamine N-coconut oil fatty acid-N-methyl taurine, triethanolamine N-palm oil fatty acid-N-ethyl taurine, magnesium N-cocoyl taurine, magnesium N-cocoyl-N-methyl taurine, magnesium N-lauroyl-N-taurine, magnesium N-lauroyl-N-methyl taurine and magnesium N-coconut oil fatty acid-N-methyl taurine. Among these, sodium cocoyl methyl taurate and sodium N-stearoyl-N-methyl taurate are preferred.The anionic surfactants can be used alone or in combination of two or more.

[0033] The content of the anionic surfactant is preferably 0.01% by mass or more, 0.03% by mass or more, 0.05% by mass or more, or 0.07% by mass or more, relative to the total amount of the cosmetic, and is preferably 1.0% by mass or less, 0.7% by mass or less, 0.5% by mass or less, or 0.3% by mass or less.

[0034] In addition to the above-mentioned components, the cosmetic of the present invention can contain optional components typically used in cosmetics and pharmaceuticals. Optional components include, for example, surfactants, moisturizers, lower alcohols, sequestering agents, neutralizing agents, pH adjusters, antioxidants, preservatives, drugs, UV absorbers, powder components, fragrances, etc. As long as the effects of the present invention are achieved, one or more optional components can be contained in the cosmetic.

[0035] The formulation of the cosmetic according to the present invention is not particularly limited, but is preferably in the form of an aqueous cosmetic or an oil-in-water emulsion cosmetic. In an aqueous cosmetic or an oil-in-water emulsion cosmetic, the aqueous phase comes into contact with the skin first, providing a moisturizing feel to the skin and enabling the effects of the present invention to be more clearly felt.

[0036] Examples of cosmetics according to the present invention include skin care cosmetics (e.g., lotion, emulsion, cream, serum, pack, mask, etc.), makeup cosmetics (e.g., foundation, makeup base, etc.), skin cleansers (e.g., face wash, makeup remover, etc.), sunscreen cosmetics, etc. Note that these forms are merely examples, and the cosmetics according to the present invention are not limited to these forms. The cosmetic composition according to the present invention can be produced by a conventional method. [Example]

[0037] The present invention will be described in detail based on the following examples, but the present invention is not limited to these examples. Unless otherwise specified, the contents are expressed in mass % relative to the total amount.

[0038] [Examples 1 to 3 and Comparative Examples 1 to 3] According to the formulations shown in Table 1, aqueous cosmetic compositions of Reference Example 1, Reference Example 2, Examples 1 to 3, and Comparative Examples 1 to 3 were prepared. [Table 1]

[0039] [Usability rating 1: Smoothness] The cosmetics prepared above were applied to the skin by a panel of five experts, and the usability was evaluated for smoothness during application according to the following criteria. Smoothness during application means that the cosmetic does not feel sticky on the skin during application. The results are shown in Table 1. A: All five participants rated the results as no change from the standard. B: 1 to 2 people evaluated that they felt a tugging sensation during application compared to the standard. C: Three or more people evaluated that they felt a tugging sensation during application compared to the standard.

[0040] [Usability rating 2: Non-stickiness] The cosmetics prepared above were applied to the skin by a panel of five experts, and the non-stickiness after application was evaluated. The results are shown in Table 1. A: All five participants rated the results as no change from the standard. B: 1 to 2 people evaluated that they felt sticky after application compared to the standard. C: Three or more people evaluated that they felt stickiness after application compared to the standard.

[0041] In usability evaluations 1 and 2, Reference Example 1, which contains component (A) but not component (B), was compared with Examples 1 to 3, which contain component (A) and different contents of component (B). Reference Example 2, which contains PPG-13 decyltetradeceth-24 instead of component (A) but not component (B), was compared with Comparative Examples 1 to 3, which contain PPG-13 decyltetradeceth-24 and different contents of component (B).

[0042] [Examples 4 to 7 and Comparative Examples 4 to 6] Oil-in-water emulsion cosmetics of Examples 4 to 7 and Comparative Examples 4 to 6 were prepared with the formulations shown in Table 2. Usability evaluations 1 and 2 were conducted according to the same criteria as in Examples 1 to 3 and Comparative Examples 1 to 3. The results obtained are shown in Table 2. [Table 2]

[0043] In usability evaluations 1 and 2, Reference Example 3, which contained component (A) but not component (B), was compared with Examples 4 to 7, which contained component (A) and different contents of component (B). Reference Example 4, which contained PPG-13 decyltetradeceth-24 instead of component (A) but not component (B), was compared with Comparative Examples 4 to 6, which contained PPG-13 decyltetradeceth-24 and different contents of component (B).

Claims

1. (A) polyglycerol fatty acid ester, (B) a pyrimidylpyrazole compound represented by formula (1) or a salt thereof, and (C) water; A cosmetic comprising: 【Chemistry 1】 (In the formula, R 1 , R 3 , R 4 and R 6 are each independently C 1-3 is an alkyl group, and R 2 and R 5 are each independently a hydrogen atom or C 1-3 alkyl group)

2. R 2 and R 5 The cosmetic according to claim 1, wherein is a hydrogen atom.

3. R 1 , R 3 , R 4 and R 6 The cosmetic preparation according to claim 1 or 2, wherein is a methyl group.

4. 3. The cosmetic according to claim 1, wherein the number of carbon atoms in the fatty acid moiety of the polyglycerol fatty acid ester is 12 or more and 17 or less.

5. 3. The cosmetic preparation according to claim 1, wherein the polyglycerin moiety in the polyglycerin fatty acid ester is a dimer or more and a decamer or less.

6. 3. The cosmetic preparation according to claim 1, wherein component (A) is polyglyceryl-6 laurate or polyglyceryl-6 myristate.

7. 3. The cosmetic according to claim 1, wherein the content of component (A) is 0.1% by mass or more and 10% by mass or less, based on the total amount of the cosmetic.

8. 3. The cosmetic according to claim 1, wherein the content of component (B) is 0.01% by mass or more and 1.5% by mass or less, based on the total amount of the cosmetic.

9. The cosmetic according to claim 1 or 2, wherein the content of the oil component (D) is 0 mass % or more and 40 mass % or less relative to the total amount of the cosmetic.

10. The cosmetic according to claim 1 or 2, which is an aqueous cosmetic or an oil-in-water emulsion cosmetic.

Citation Information

Patent Citations

  • Skin whitening agent and external preparation for the skin

    WO2009099192A1