Cosmetic
The cosmetic formulation of pyrimidylpyrazole compounds with fatty acid polyoxyethylene glyceryl addresses the stickiness issue in whitening agents, enhancing usability and stability at high temperatures.
Patent Information
- Application Number
- PCT/JP2024/039905
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2023-11-24
- Filing Date
- 2024-11-11
- Publication Date
- 2025-05-30
AI Technical Summary
Pyrimidylpyrazole compounds used in cosmetics as whitening agents tend to cause stickiness, which affects their usability and stability, especially at high temperatures.
A cosmetic formulation combining a pyrimidylpyrazole compound or its salt with fatty acid polyoxyethylene glyceryl, along with an oil component and water, to enhance usability and high-temperature stability by reducing stickiness.
The combination achieves excellent usability and high-temperature stability, ensuring the cosmetic remains fresh during application and suppresses stickiness after application.
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Abstract
Description
Cosmetics
[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.
[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 such abnormal melanin deposition, 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 (see, for example, Patent Document 1).
[0003] International Publication No. 2009 / 099192
[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. The present inventors have surprisingly found that by using a cosmetic containing a combination of a pyrimidylpyrazole compound or its salt and a fatty acid polyoxyethylene glyceryl, it is possible to achieve excellent usability and high-temperature stability. The present invention is based on these findings.
[0005] According to the present invention, the following inventions are provided: [1] A cosmetic comprising (A) a fatty acid polyoxyethylene glyceryl, (B) a pyrimidylpyrazole compound represented by formula (1) or a salt thereof, (C) an oil component, and (D) water. (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 [2] R is an alkyl group 2 and R 5 [3] The cosmetic preparation according to [1], wherein R is a hydrogen atom. 1 , R 3 , R 4and R 6 is a methyl group. [4] The cosmetic preparation according to any one of [1] to [3], further comprising (E) an alkyl-modified carboxyvinyl polymer. [5] The cosmetic preparation according to [4], wherein component (E) is an (acrylates / C10-30 alkyl acrylate) crosspolymer. [6] The cosmetic preparation according to any one of [1] to [5], further comprising (F) a carboxyvinyl polymer. [7] The cosmetic preparation according to any one of [1] to [6], wherein the blending amount of component (A) is 0.1 to 3 mass% relative to the total amount of the cosmetic preparation. [8] The cosmetic preparation according to any one of [1] to [7], wherein the blending amount of component (B) is 0.01 to 1 mass% relative to the total amount of the cosmetic preparation. [9] The cosmetic preparation according to any one of [1] to [8], wherein the viscosity measured at 30°C using a Brookfield type rotational viscometer is 10,000 mPa s or more.
[10] The cosmetic according to any one of [1] to [9], which is an oil-in-water emulsion cosmetic.
[0006] According to the present invention, it is possible to provide a cosmetic preparation that has excellent high-temperature stability and an excellent feel when used, and in particular, that provides a fresh feeling during application and suppresses stickiness after application. Specific Description of the Invention
[0007] The present invention relates to a cosmetic comprising (A) a fatty acid polyoxyethylene glyceryl, (B) a pyrimidylpyrazole compound having a specific structure or a salt thereof, (C) an oil component, and (D) water.
[0008] (A) Fatty Acid Polyoxyethylene Glyceryl The cosmetic composition according to the present invention comprises (A) a fatty acid polyoxyethylene glyceryl. Examples of component (A) include PEG-10 glyceryl stearate, PEG-15 glyceryl stearate, PEG-20 glyceryl stearate, PEG-30 glyceryl stearate, PEG-40 glyceryl stearate, PEG-8 glyceryl isostearate, PEG-10 glyceryl isostearate, PEG-15 glyceryl isostearate, PEG-20 glyceryl isostearate, PEG-25 glyceryl isostearate, PEG-30 glyceryl isostearate, PEG-40 glyceryl isostearate, PEG-50 glyceryl isostearate, and PEG-60 glyceryl isostearate. glyceryl diisostearate, PEG-20 glyceryl diisostearate, PEG-30 glyceryl diisostearate, PEG-60 glyceryl diisostearate, PEG-30 glyceryl trioleate, PEG-40 glyceryl trioleate, PEG-50 glyceryl trioleate, PEG-60 glyceryl trioleate, PEG-30 glyceryl triisostearate, PEG-40 glyceryl triisostearate, PEG-50 glyceryl triisostearate, PEG-60 glyceryl triisostearate, PEG-9 glyceryl laurate, and the like are mentioned, preferably PEG-60 glyceryl isostearate.
[0009] The component (A) may be blended in one or more types. The blending amount of the component (A) is preferably 0.1 to 3 mass%, more preferably 0.1 to 1.5 mass%, and even more preferably 0.3 to 0.8 mass%, relative to the total amount of the cosmetic.
[0010] (B) Pyrimidylpyrazole Compound or Salt Thereof The cosmetic composition according to the present invention comprises (B) a pyrimidylpyrazole compound represented by formula (1) or a salt thereof. In the formula, R 1 , R 3 , R 4 and R 6 are each independently C 1-3R 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, and more preferably a methyl group. 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.
[0011] 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.
[0012] The component (B) may be blended in one or more types. The blending amount of the component (B) is preferably 0.01 to 1 mass %, more preferably 0.05 to 0.8 mass %, even more preferably 0.2 to 0.7 mass %, and still more preferably 0.3 to 0.6 mass %, relative to the total amount of the cosmetic.
[0013] (C) Oil The cosmetic preparation according to the present invention comprises (C) oil. Examples of component (C) include silicone oil, hydrocarbon oil, higher fatty acid, higher alcohol, ester oil, liquid oil, solid oil, and semi-solid oil, with silicone oil, hydrocarbon oil, higher alcohol, and ester oil being preferred.
[0014] 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.
[0015] Examples of hydrocarbon oils include isododecane, isohexadecane, isoparaffin, mineral oil (liquid paraffin), ozokerite, squalane, pristane, paraffin, ceresin, squalene, petrolatum, microcrystalline wax, and hydrogenated polydecene.
[0016] 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).
[0017] 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.
[0018] Examples of ester oils include octyl octanoate, nonyl nonanoate, cetyl octanoate, isopropyl myristate (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, and isocetyl isostearate. , cholesteryl 12-hydroxystearate, ethylene glycol di-2-ethylhexanoate, dipentaerythritol fatty acid ester, N-alkyl glycol monoisostearate, neopentyl glycol dicaprate, tripropylene glycol pivalate, diisostearyl malate, glycerin di-2-heptylundecanoate, glycerin diisostearate, trimethylolpropane tri-2-ethylhexanoate, trimethylolpropane triisostearate Ingredients: Pentaerythritol tetra-2-ethylhexanoate, Glycerin tri-2-ethylhexanoate, Glycerin trioctanoate, Glycerin triisopalmitate, Trimethylolpropane triisostearate, Cetyl 2-ethylhexanoate-2-ethylhexyl palmitate, Glycerin trimyristate, Tri-2-heptylundecanoic acid glyceride, Castor oil fatty acid methyl ester, Oleyl oleate, Acetoglyceride, 2-heptylundecanoate palmitate decyl, 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, macadamia nut fatty acid phytosteryl, and the like.
[0019] 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.
[0020] The component (C) may be blended in one or more types. The blending amount of the component (C) is preferably 1 to 30 mass %, more preferably 10 to 30 mass %, based on the total amount of the cosmetic.
[0021] (D) Water The cosmetic according to the present invention comprises (D) water. As the water, water used in cosmetics, quasi-drugs, etc. can be used, such as purified water, ion-exchanged water, tap water, etc. The blending amount of water is preferably 1 to 90% by mass, more preferably 50 to 80% by mass, based on the total amount of the cosmetic according to the present invention.
[0022] (E) Alkyl-Modified Carboxyvinyl Polymer The cosmetic preparation according to the present invention may further comprise (E) an alkyl-modified carboxyvinyl polymer. Component (E) is an acrylate / alkyl methacrylate copolymer, a polymer in which at least a portion of the carboxyl groups of a polymer having acrylic acid or methacrylic acid as its main chain are esterified with an alkyl group. The alkyl group bonded via an ester bond may be linear or branched, and preferably has 10 to 30 carbon atoms. Component (E) is preferably a crosspolymer in which polymers or copolymers containing alkyl acrylate or alkyl methacrylate as polymerization units are crosslinked with each other. Examples of component (E) include acrylates / alkyl acrylate (C10-30) crosspolymers.
[0023] The component (E) may be blended in one or more types. The blending amount of the component (E) is preferably 0.005 to 1.5 mass%, more preferably 0.01 to 0.5 mass%, and even more preferably 0.05 to 0.3 mass%, relative to the total amount of the cosmetic.
[0024] (F) Carboxyvinyl Polymer The cosmetic according to the present invention may further contain (F) a carboxyvinyl polymer (also known as a "carbomer"). Component (F) is used as a general-purpose thickener for cosmetics and is a polymer containing acrylic acid as a monomer unit. The carboxyl group of the carboxyvinyl polymer in question is unmodified, i.e., it is not included in component (E). Such component (F) is generally commercially available, and is sold under the names Hiviswako (trade name, manufactured by Wako Pure Chemical Industries, Ltd.), Sintaren (trade name, manufactured by 3V SIGMA), Carbopol (trade name, manufactured by Goodrich Chemicals), etc. These thickeners are crosslinked polymers having a chemically crosslinked structure. Aqueous dispersions of such crosslinked polymers have an extremely high thickening effect.
[0025] The blending amount of component (F) is preferably 0.01 to 1.5 mass %, more preferably 0.05 to 0.8 mass %, and even more preferably 0.1 to 0.5 mass %, relative to the total amount of the cosmetic.
[0026] In addition to the above-mentioned components, the cosmetic of the present invention can contain optional components typically used in cosmetics and pharmaceuticals, such as moisturizers, lower alcohols, sequestering agents, neutralizing agents, pH adjusters, antioxidants, preservatives, drugs, ultraviolet absorbers, powder components, fragrances, etc. One or more of these can be contained as long as the effects of the present invention are achieved.
[0027] The formulation of the cosmetic according to the present invention is not particularly limited, but it is preferably in the form of an oil-in-water emulsion cosmetic. In an oil-in-water emulsion cosmetic, the external phase that first comes into contact with the skin is the aqueous phase, which gives the skin a fresh feeling and makes it possible to more effectively experience the effects of the present invention.
[0028] 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, ointments, etc. Note that these forms are merely examples, and the cosmetics according to the present invention are not limited to these forms.
[0029] The cosmetic of the present invention can be produced by any conventional method without any particular limitation on the emulsification method. The viscosity is not particularly limited, but is preferably 10,000 mPa·s or more, and more preferably 10,000 to 120,000 mPa·s. The viscosity can be measured at 30°C using a Brookfield viscometer.
[0030] 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.
[0031] [Examples 1 to 6 and Comparative Examples 1 to 5] Oil-in-water emulsion cosmetics of Examples 1 to 6 and Comparative Examples 1 to 5 were prepared according to the formulations shown in Table 1.
[0032] [Viscosity] The viscosity of the cosmetic material prepared above was measured at 30° C. using a BH type viscometer (No. 6 rotor, rotation speed 10 rpm). The results obtained are shown in Table 1.
[0033] [Usability Evaluations (1) and (2)] Expert panels applied the cosmetics prepared above to the skin, and the sensation of freshness during application was scored according to the following criteria. The ten expert panels then totaled their scores to evaluate usability. The results are shown in Table 1. +1: Feels fresher than the control during application. 0: Feels the same level of freshness during application as the control. -1: Feels fresher than the control during application. In usability evaluation (1), the cosmetics of Examples 1 to 3 and Examples 4 to 6 were evaluated using Comparative Example 1 or 2, which did not contain component (B), as a control. In usability evaluation (2), cosmetics containing the same amount of component (B) were used as a control; that is, Examples 1 and 4 were evaluated using Comparative Example 3 as a control, Examples 2 and 5 were evaluated using Comparative Example 4 as a control, and Examples 3 and 6 were evaluated using Comparative Example 5 as a control.
[0034] [Usability Evaluation (3)] Expert panels applied the cosmetics prepared above to the skin, and the usability was scored for non-stickiness after application according to the following criteria, with the total points scored by the 10 expert panels. The results are shown in Table 1. +1: Less sticky than the control after application. 0: Similar level of stickiness after application compared to the control. -1: More sticky than the control after application. In usability evaluation (1), the cosmetics of Examples 1 to 3 and Examples 4 to 6 were evaluated using Comparative Example 1 or 2, which did not contain component (B), as a control. In usability evaluation (2), cosmetics containing the same amount of component (B) were used as a control; that is, Examples 1 and 4 were evaluated using Comparative Example 3 as a control, Examples 2 and 5 were evaluated using Comparative Example 4 as a control, and Examples 3 and 6 were evaluated using Comparative Example 5 as a control.
[0035] [High-Temperature Stability Evaluations (1) and (2)] Immediately after preparation, all of the cosmetics obtained above were in the form of a uniform single layer. These cosmetics were left at 60°C for one week in high-temperature stability evaluation (1), and at 70°C for three days in high-temperature stability evaluation (2). The appearance was then visually observed and evaluated according to the following criteria. The results obtained are shown in Table 1. A: A single uniform layer was maintained. B: A single uniform layer could not be maintained, and separation was observed.
Claims
1. A cosmetic comprising: (A) a fatty acid polyoxyethylene glyceryl; (B) a pyrimidylpyrazole compound represented by formula (1) or a salt thereof; (C) an oil; and (D) water. (In the formula, R 1 , R 3 , R 4 and R 6 are each independently 1-3 R is an alkyl group; 2 and R 5 Each independently represents a hydrogen atom or C 1-3 is an alkyl group) 2. R 2 and R 5 The cosmetic preparation 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. The cosmetic preparation according to claim 1 or 2, further comprising (E) an alkyl-modified carboxyvinyl polymer.
5. The cosmetic preparation according to claim 4, wherein component (E) is an acrylates / C10-30 alkyl acrylate crosspolymer.
6. The cosmetic preparation according to claim 1 or 2, further comprising (F) a carboxyvinyl polymer.
7. The cosmetic according to claim 1 or 2, wherein the blending amount of component (A) is 0.1 to 3 mass % relative to the total amount of the cosmetic.
8. The cosmetic according to claim 1 or 2, wherein the blending amount of component (B) is 0.01 to 1 mass % relative to the total amount of the cosmetic.
9. The cosmetic preparation according to claim 1 or 2, which has a viscosity measured at 30° C. using a B-type rotational viscometer of 10,000 mPa·s or more.
10. The cosmetic according to claim 1 or 2, which is an oil-in-water emulsion cosmetic.
Citation Information
Patent Citations
Skin whitening preparation
JP2009263252A
cosmetic
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Skin whitening agent and external preparation for the skin
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Skin cosmetic
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