JP2010138122A - Acne treatment agent - Google Patents

Abstract

（Ｒ¹はヒドロキシル基、カルボニル基又はアミノ基が置換していてもよい、炭素数４〜３０の炭化水素基；Ｙはメチレン基、メチン基又は酸素原子；Ｘ¹、Ｘ²、及びＸ³は水素原子、ヒドロキシル基又はアセトキシ基、Ｘ⁴は水素原子、アセチル基又はグリセリル基か、隣接する酸素原子と一緒になってオキソ基を形成；Ｒ²及びＲ³は水素原子、ヒドロキシル基、ヒドロキシメチル基又はアセトキシメチル基；ａ個のＲは水素原子又はアミジノ基か、ヒドロキシル基、ヒドロキシアルコキシ基、アルコキシ基及びアセトキシ基から選ばれる置換基を有していてもよい総炭素数１〜８の炭化水素基；ａは２）、
（Ｂ）イソプロピルメチルフェノール、
（Ｃ）ポリオール、
（Ｄ）水
を含有し、成分（Ａ）と成分（Ｂ）の質量割合が、０＜（Ｂ）／（Ａ）≦５であるニキビ改善剤。
【選択図】なし[PROBLEMS] To provide a composition having good stability and excellent effect for preventing and treating acne.
(A) Sphingosines represented by the general formula (1)

(R ¹ is a hydrocarbon group having 4 to 30 carbon atoms which may be substituted by a hydroxyl group, a carbonyl group or an amino group; Y is a methylene group, a methine group or an oxygen atom; X ¹ , X ² and X ³ Is a hydrogen atom, a hydroxyl group or an acetoxy group, X ⁴ is a hydrogen atom, an acetyl group or a glyceryl group, or together with an adjacent oxygen atom to form an oxo group; R ² and R ³ are a hydrogen atom, a hydroxyl group, a hydroxy group A methyl group or an acetoxymethyl group; a R is a hydrogen atom or an amidino group, a hydroxyl group, a hydroxyalkoxy group, an alkoxy group and an acetoxy group, which may have a substituent having 1 to 8 carbon atoms in total A hydrocarbon group; a is 2),
(B) isopropylmethylphenol,
(C) polyol,
(D) The acne improving agent which contains water and the mass ratio of a component (A) and a component (B) is 0 <(B) / (A) <= 5.
[Selection figure] None

Description

  The present invention relates to an acne-improving agent that is excellent in acne prevention and treatment effects.

  Acne, or acne vulgaris, is a skin disease that occurs mainly during puberty, and generally increases sebum secretion and retention, hyperkeratosis and obstruction of the capillaries, bacterial growth such as Propionibacterium acnes in the capillaries, Several factors are considered to be interrelated skin diseases. Acne is a cosmetic problem, especially for adolescents, as acne occurs frequently on the face.

  In order to deal with the above factors, isopropylmethylphenol is mainly used as an antibacterial agent for preventing and treating acne (for example, Patent Document 1, Patent Document 2, and Patent Document 3). However, since isopropylmethylphenol is hardly soluble in water, there is a problem that it cannot be added to the aqueous phase as it is. In the Example of patent document 1 and patent document 2, ethanol is used 10 mass% or more as a solvent. In Patent Document 3, a large amount of a surfactant and an oil such as phospholipid and polyoxyethylene alkyl ether is used, and isopropylmethylphenol is solubilized or emulsified to prepare a formulation.

However, when a large amount of ethanol is used, there is a problem that it is difficult for a person who feels irritation to the skin due to ethanol. Further, when emulsified and used, isopropylmethylphenol is taken into the micelle, so that the amount of isopropylmethylphenol dissolved in the aqueous phase decreases. As a result, there is a problem that a sufficient bactericidal effect corresponding to the blending amount cannot be obtained, and the anti-acne effect inherent to isopropylmethylphenol cannot be utilized to the maximum extent.
JP-A-3-157311 JP 2001-139412 A JP 2007-308430 A

  An object of the present invention is to provide a composition having good stability and excellent effect for preventing and treating acne.

  The present inventors combined sphingosines and isopropylmethylphenol at a specific ratio, dissolved in a polyol, and made an aqueous agent, thereby exhibiting an excellent bactericidal power against acne bacteria, and a stable preparation. It was found that it can be obtained.

The present invention includes the following components (A), (B), (C) and (D):
(A) Sphingosines represented by the general formula (1)

(In the formula, R ¹ represents a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 4 to 30 carbon atoms, which may be substituted by a hydroxyl group, a carbonyl group or an amino group; A methylene group, a methine group or an oxygen atom; each of X ¹ , X ² and X ³ independently represents a hydrogen atom, a hydroxyl group or an acetoxy group, and X ⁴ represents a hydrogen atom, an acetyl group or a glyceryl group Together with an adjacent oxygen atom to form an oxo group (provided that when Y is a methine group, ^one of X ¹ and X ² is a hydrogen atom and the other does not exist. X ⁴ is an oxo group) when forming, X ³ is absent);. R ² and R ³ are each independently a hydrogen atom, a hydroxyl group, a hydroxymethyl group or an acetoxymethyl group; a is a number of 2, the a number Each R is independently a hydrogen atom or amidino A linear or branched saturated or unsaturated hydrocarbon group having 1 to 8 carbon atoms which may have a substituent selected from a hydroxyl group, a hydroxyalkoxy group, an alkoxy group and an acetoxy group The broken line indicates that it may be an unsaturated bond),
(B) isopropylmethylphenol,
(C) polyol,
(D) An acne improver containing water and having a mass ratio of component (A) to component (B) of 0 <(B) / (A) ≦ 5 is provided.

  The acne-improving agent of the present invention has excellent storage stability, low irritation, a high bactericidal effect, and an excellent acne prevention and treatment effect.

The sphingosine component (A) used in the present invention is represented by the general formula (1).
In the formula, R ¹ represents a linear, branched or cyclic saturated or unsaturated hydrocarbon having 4 to 30 carbon atoms, which may be substituted with a hydroxyl group, a carbonyl group or an amino group, preferably a hydroxyl group A linear alkyl group having 7 to 24 carbon atoms which may be substituted. In particular, a linear alkyl group having 10 to 24 carbon atoms and a linear alkyl group having 10 to 24 carbon atoms having a hydroxyl group at the carbon atom bonded to Y in the general formula (1) are preferable. Specifically, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a 1-hydroxytridecyl group, and a 1-hydroxypentadecyl group are preferable.

Y represents a methylene group (CH ₂ ), a methine group (CH), or an oxygen atom.
X ¹ , X ² , and X ³ each independently represent a hydrogen atom, a hydroxyl group, or an acetoxy group, and X ⁴ represents an oxo group together with a hydrogen atom, an acetyl group, a glyceryl group, or an adjacent oxygen atom. The substituent to be formed is shown. In particular, it is preferable that 0 to ¹ of X ¹ , X ² , and X ³ are hydroxyl groups, the remainder is a hydrogen atom, and X ⁴ is a hydrogen atom. When Y is a methine group, only ^one of X ¹ and X ² is a hydrogen atom, and the other does not exist. Also, when X ⁴ forms an oxo group, X ³ does not exist.

R ² and R ³ each independently represent a hydrogen atom, a hydroxyl group, a hydroxymethyl group or an acetoxymethyl group, and R ³ is particularly preferably a hydrogen atom.

A represents a number of 2, and when a is 2, R represents the following R ⁴ and R ⁵ .

R ⁴ and R ⁵ are each independently a hydrogen atom or an amidino group, or may have a substituent selected from a hydroxyl group, a hydroxyalkoxy group, an alkoxy group, and an acetoxy group, having 1 to 8 carbon atoms in total A linear or branched saturated or unsaturated hydrocarbon group. Here, the hydroxyalkoxy group that can be substituted with an alkyl group is preferably a linear or branched hydroxyalkoxy group having 1 to 7 carbon atoms. Moreover, as an alkoxy group, a C1-C7 linear or branched alkoxy group is preferable. R ⁴ and R ⁵ include, for example, a hydrogen atom; a linear or branched alkyl group such as methyl, ethyl, propyl, 2-ethylhexyl and isopropyl; an alkenyl group such as vinyl and allyl; an amidino group; hydroxymethyl, 2 -Hydroxyethyl, 1,1-dimethyl-2-hydroxyethyl, 2-hydroxypropyl, 2,3-dihydroxypropyl, 2-hydroxy-3-methoxypropyl, 2,3,4,5,6-pentahydroxyhexyl 1,1-bis (hydroxymethyl) ethyl, 2- (2-hydroxyethoxy) ethyl, 2-methoxyethyl, 1-methyl-2-hydroxyethyl, 3-hydroxypropyl, 3-methoxypropyl, 1,1- Hydroxyl groups such as bis (hydroxymethyl) -2-hydroxyethyl, hydroxyalkoxy groups and Examples thereof include hydrocarbon groups having 1 to 8 carbon atoms substituted by 1 to 6 groups selected from alkoxy groups.

  In particular, a hydrogen atom or a hydroxyl group such as a methyl group, 2-hydroxyethyl, 1,1-dimethyl-2-hydroxyethyl, 1,1-bis (hydroxymethyl) ethyl, 2- (2-hydroxyethoxy) ethyl, and the like Alkyl groups which 1 to 3 groups selected from hydroxyalkoxy groups may be substituted are preferred.

As the sphingosine represented by the general formula (1), natural or natural sphingosines represented by the following general formula (2) and derivatives thereof (hereinafter referred to as natural sphingosine), or the general formula (3) Pseudo-type sphingosines (hereinafter referred to as pseudo-type sphingosine) having a sphingosine structure represented by
(I) A natural sphingosine represented by the general formula (2).

Wherein R ⁷ represents a linear alkyl group having 7 to 24 carbon atoms which may be substituted by a hydroxyl group; Y ₁ represents a methylene group or a methine group; X ⁵ , X ⁶ and X ⁷ are each Independently represents a hydrogen atom, a hydroxyl group or an acetoxy group, and X ⁸ represents a hydrogen atom or together with an adjacent oxygen atom forms an oxo group (provided that when Y ₁ is a methine group, X ⁵ And X ⁶ represents a hydrogen atom, and the other does not exist. When X ⁸ forms an oxo group, X ⁷ does not exist.); R ⁸ represents a hydroxymethyl group or an acetoxymethyl group; Each R ₁ is independently a hydrogen atom or an amidino group, or may have a substituent selected from a hydroxyl group, a hydroxyalkoxy group, an alkoxy group, and an acetoxy group. A chain alkyl group; a is 2 It is shown; the broken line indicates that may be unsaturated bond)

R ⁷ is preferably a linear alkyl group having 7 to 24 carbon atoms, and particularly preferably a linear alkyl group having 13 to 24 carbon atoms. a is preferably 2, and each R ₁ is independently a hydrogen atom or a linear alkyl group having 1 to 4 carbon atoms.

Specific examples of the natural sphingosine represented by the general formula (2) include natural sphingosine, dihydrosphingosine, phytosphingosine, sphingadienin, dehydrosphingosine, dehydrophytosphingosine, and N-alkyl derivatives thereof (for example, N-methyl form) and the like.
These sphingosines may be either natural (D (+)) optically active or non-natural (L (-)) optically active, or a mixture of natural and non-natural types. May be used. The relative configuration of the above compound may be a natural configuration, a non-natural configuration other than that, or a mixture thereof.
In particular, PHYTOSPHINGOSINE (INCI name: 8th Edition) and the following formula are preferable.

These may be any of natural extracts and synthetic products, and commercially available products can be used.
Examples of commercially available natural sphingosine include D-Sphingosine (4-Sphingenine) (SIGMA-ALDRICH), DS-phytosphingosine (DOOSAN), and phytosphingosine (Degussa).

(II) A pseudo-type sphingosine represented by the general formula (3).

(In the formula, R ⁹ represents a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 10 to 22 carbon atoms which may be substituted with a hydroxyl group; X ⁹ represents a hydrogen atom, an acetyl group or A glyceryl group; a R ₂ each independently represents a hydrogen atom or an amidino group, or a total carbon which may have a substituent selected from a hydroxyl group, a hydroxyalkoxy group, an alkoxy group and an acetoxy group A linear or branched, saturated or unsaturated hydrocarbon group of 1 to 8 is represented by a being a number of 2)

Here, as R ⁹ , an iso-branched alkyl group having 14 to 20 carbon atoms is preferable, and an isostearyl group is particularly preferable. The isostearyl group is most preferably an isostearyl group obtained by using, as a raw material oil, an isosteal alcohol derived from a by-product during production of a dimer acid using a fatty acid derived from an animal or vegetable oil.
When a is 2, R ₂ represents R ¹⁰ and R ¹¹ .

R ¹⁰ and R ¹¹ are, for example, a hydrogen atom; a linear or branched alkyl group such as methyl, ethyl, propyl, 2-ethylhexyl and isopropyl; an alkenyl group such as vinyl and allyl; an amidino group; -Hydroxyethyl, 1,1-dimethyl-2-hydroxyethyl, 2-hydroxypropyl, 2,3-dihydroxypropyl, 2-hydroxy-3-methoxypropyl, 2,3,4,5,6-pentahydroxyhexyl 1,1-bis (hydroxymethyl) ethyl, 2- (2-hydroxyethoxy) ethyl, 2-methoxyethyl, 1-methyl-2-hydroxyethyl, 3-hydroxypropyl, 3-methoxypropyl, 1,1- Hydroxy, hydroxyalkoxy and alkoxy such as bis (hydroxymethyl) -2-hydroxyethyl Et alkyl group having a total carbon number of 1 to 8 having a substituent selected and the like.
In particular, one of R ¹⁰ and R ¹¹ is a hydrogen atom and the other is 2-hydroxyethyl, 1,1-dimethyl-2-hydroxyethyl, 1,1-bis (hydroxymethyl) ethyl, 2- (2- Secondary amines which are hydroxyethoxy) ethyl are preferred.

As the pseudo-type sphingosine, R ⁹ is an isostearyl group, X ⁹ is a hydrogen atom, R ¹⁰ is a hydrogen atom, R ¹¹ is a 2-hydroxyethyl group, 1,1-bis (hydroxymethyl) ethyl group, 1,1 -It is preferable that 1-3 substituted by hydroxyl groups and hydroxyalkoxy groups such as dimethyl-2-hydroxyethyl group or 2- (2-hydroxyethoxy) ethyl group are substituted alkyl groups.
Specific examples of the pseudo-sphingosine include the following pseudo-sphingosines (i) to (iv).

  Among these, as component (A), phytosphingosine, dihydrosphingosine, and 1- (2-hydroxyethylamino) -3-isostearyloxy-2-propanol represented by the above formula (ii) are preferable. (2-Hydroxyethylamino) -3-isostearyloxy-2-propanol is preferred.

  One or more components (A) can be used, and the total composition contains 0.01 to 10% by mass, particularly 0.02 to 1.5% by mass, and more preferably 0.02 to 0.2% by mass. Is preferable in terms of stability.

  The component (B) isopropylmethylphenol used in the present invention is a fungicide and is effective in removing acne bacteria. Component (B), isopropylmethylphenol, is preferably contained in the total composition in an amount of 0.01 to 1% by mass, particularly 0.02 to 0.5% by mass, and more preferably 0.05 to 0.1% by mass.

As the polyol of component (C) used in the present invention, an organic compound having 2 or 3 hydroxyl groups in the molecule is preferable, and one having 2 hydroxyl groups is particularly preferable.
Examples of such polyols include glycerin, ethylene glycol, propylene glycol, polyethylene glycol having a molecular weight of 1500 or less, dipropylene glycol, 1,3-butylene glycol and the like. Among these, propylene glycol, dipropylene glycol, and 1,3-butylene glycol are preferable. These are excellent in that the components (A) and (B) can be solubilized and the bactericidal effect is not impaired.

  The component (C) polyol contains 0.01 to 20% by weight, more preferably 0.1 to 15% by weight, and particularly 1 to 15% by weight in the total composition. It is preferable because it helps to prevent stickiness.

  The component (D) water used in the present invention functions as a solvent in the composition and occupies the remaining amount, but is preferably contained in an amount of 70 to 90% by mass in the entire composition.

  Component (B), isopropylmethylphenol, has a high melting point of 110 ° C. and is insoluble in water. For this reason, in the formulation so far, it was often used by being solubilized in ethanol, polyol, polar oil or the like. However, when ethanol is used, there is a problem that it may cause irritation when used by a person sensitive to ethanol and is difficult to use. Also, there is a method of dissolving in polyol and using it, but it is not effective because it crystallizes and precipitates when mixed with water. On the other hand, when solubilized and used in oils, particularly polar oils, the sterilizing effect of isopropylmethylphenol is lost and the meaning of blending is lost. Although there were problems as described above, in the present invention, when the component (A) and the component (B) are combined at a specific ratio, the melting point of the component (B) is lowered, and the component (B) should exist as a liquid even at room temperature. Can do. Furthermore, until now, when the component (B) is dissolved in the polyol of the component (C) and then mixed with the component (D), the component (B) has been precipitated. By combining them, precipitation as crystals can be suppressed.

  In the present invention, the mass ratio of the component (A) to the component (B) is 0 <(B) / (A) ≦ 5, but 0.01 <(B) / (A) ≦ from the viewpoint of the melting point drop. 5 is preferable, and more preferably 0.01 <(B) / (A) ≦ 3.

  The acne improving agent of the present invention can further contain a component (E) a cationic polymer or a cationic surfactant. Ingredient (E) not only improves the applicability of the agent to the skin, but also suppresses crystal precipitation of ingredient (B), further improves long-term storage stability, and maintains and improves the bactericidal effect. be able to.

  As the cationic polymer, poly (dimethyldiallylammonium halide) type cationic polymer, dimethyldiallylammonium halide and acrylamide copolymer cationic polymer, or quaternary nitrogen-containing cellulose ether, or polyethylene glycol, epichlorohydrin, propyleneamine and tallow fatty acid The resulting condensation product of taroylamine or cocoylamine, or cationized vinylpyrrolidone / dimethylaminoethyl methacrylate copolymer, diethyl sulfate of N, N-dimethylaminoethyl methacrylate / N, N-dimethylacrylamide / polyethylene glycol dimethacrylate Examples thereof include a copolymer (polyquaternium-52).

  Examples of the poly (dimethyldiallylammonium halide) type cationic polymer include Merquat 100 (Nalco). Examples of the copolymer-type cationic polymer of dimethyldiallylammonium halide and acrylamide include Merquat 550 (Nalco). Examples of the quaternary nitrogen-containing cellulose include polymer JR-400 (Polymer JR-400), polymer JR-125 (Polymer JR-125), polymer JR-30M (Polymer JR-30M) (Union Carbide). It is done. Examples of the condensation product of polyethylene glycol, epichlorohydrin, propyleneamine and taroylamine or cocoylamine include Polyquat H (Henkel). Examples of the cationized vinyl pyrrolidone / dimethylaminoethyl methacrylate copolymer include Gafquat 755 and Gafquat 734 (GAF). Examples of N, N-dimethylaminoethyl diethyl methacrylate sulfate / N, N-dimethylacrylamide / polyethylene glycol dimethacrylate copolymer include Sofcare KG-301W (Kao Corporation). Furthermore, H.C. sold by Osaka Organic Chemical Industry Co., Ltd. C. Examples include the polymer series and Rhodia's Jaguar series.

  Further, as the cationic surfactant, for example, N-long chain acyl basic amino acid derivatives and acid addition salts thereof are preferable, and those represented by the following general formulas (4), (5) and (6): One type or two or more types can be selected and used.

(In the general formulas (4) to (6), R ¹³ CO represents a saturated or unsaturated fatty acid residue having 6 to 20 carbon atoms, and X represents —NH ₂ , —OCH ₃ , —OC ₂ H ₅ , — OC ₃ H ₇ , —OC ₄ H ₉ or —OCH ₂ C ₆ H ₅ is shown, and in general formula (5), n represents 3 or 4)

  More specifically, for example, N-caproyl-L-arginine methyl ester hydrochloride, N-lauroyl-L-arginine ethyl ester-DL-pyrrolidone carboxylate, N-palmitoyl-L-arginine ethyl ester hydrochloride, N -Cocoyl-L-arginine ethyl ester-DL-pyrrolidone carboxylate, N-caproyl-L-lysine methyl ester hydrochloride, N-lauroyl-L-lysine ethyl ester-DL-pyrrolidone carboxylate, N-myristoyl-L -Lysine propyl ester hydrochloride, N-cocoyl-L-lysine methyl ester-DL-pyrrolidone carboxylate, N-stearoyl-L-histidine methyl ester hydrochloride, N-oleoyl-L-histidine ethyl ester-DL-pyrrolidone Examples thereof include carboxylates.

  The cationic polymer and / or cationic surfactant can be used alone or in combination of two or more, and is preferably contained in the total composition in an amount of 0.01 to 5% by mass, particularly 0.1 to 1% by mass. .

  Furthermore, the acne improving agent of this invention can contain a component (F) polyether modified silicone. As the polyether-modified silicone, a polyether-modified silicone having an HLB of 7 or more (note that HLB indicates HLB of griffin) is preferable. Polyether-modified silicone not only provides a feeling during application, but also enhances storage stability at high temperatures and maintains a bactericidal effect.

Specific examples of the polyether-modified silicone include PEG-9 dimethicone (Shin-Etsu Silicone, KF-6013), PEG-10 dimethicone (Shin-Etsu Silicone, KF-353A), and PEG-12 dimethicone (Toray Dow Corning). , SS-2804), PEG-6 methyl ether dimethicone (Shin-Etsu Silicone, KF-618), PEG-10 methyl ether dimethicone (Toray Dow Corning, SS-2801), PEG-6 methyl ether dimethicone (Shin-Etsu Silicone) , KF-618), PEG-10 methyl ether dimethicone (Toray Dow Corning, SS-2801), PEG-11 methyl ether dimethicone (Shin-Etsu Silicone, KF-6011), PEG / PPG-20 / 20 dimethicone (SH3749). ), PEG PPG-20 / 22 butyl ether dimethicone (Shin-Etsu Silicone Co., KF-352A), PEG / PPG-27 / 9 butyl ether dimethicone (Shin-Etsu Silicone Co., KF-615A) (INCI name) and the like can be mentioned, and PEG-12 dimethicone, PEG -11 methyl ether dimethicone is preferred.
The polyether-modified silicone of component (F) is preferably contained in the total composition in an amount of 0.01 to 10% by mass, particularly 0.1 to 1% by mass.

The acne improving agent of the present invention may further contain a conventionally used acne improving component. Such components include, for example, anti-inflammatory agents such as glycyrrhetinic acid and dipotassium glycyrrhizinate; plant extracts such as asnalo, hamamelis, botpi, mugwort, buckwheat, licorice, auren; allantoin, shikonin, hinokitiol, cedrol, ε-aminocaproic acid Antibacterial agents such as benzalkonium chloride, benzethonium chloride, photosensitizer 20, adipic acid; sebum secretion inhibitors such as estradiol, vitamin B6, royal jelly extract; and oil-absorbing porous powders such as porous nylon powder and porous cellulose powder Body, sebum absorbents such as zinc oxide; and stratum corneum release agents such as salicylic acid, resorcin, and sulfur.
The effective content of these components varies depending on the type, but is preferably 0.001 to 30% by mass, and particularly preferably 0.01 to 10% by mass in the total composition.

  In addition to the above components, the acne-improving agent of the present invention is a component used in normal skin external preparations, for example, a humectant such as glycine betaine, urea, amino acid, or the like; an organic compound such as a crosslinked silicone powder or crosslinked methylpolysiloxane Powders; inorganic powders such as anhydrous silica, zinc oxide and titanium oxide; refreshing agents such as menthol and camphor; chelating agents such as edetic acid; vitamins such as ascorbic acid and tocopherol acetate; pH buffering agents, antioxidants, An ultraviolet absorber, a preservative, a fragrance | flavor, a pigment | dye, etc. can be contained.

  The acne-improving agent of the present invention is preferably pH 3-6, particularly pH 4-5, from the viewpoint of bactericidal and skin irritation mitigation. The pH is measured by COMPACT pH METER B-212 manufactured by Horiba.

  The acne improving agent of the present invention is preferably used in the form of a wiping agent, lotion, milky lotion, cosmetic liquid, pack, aerosol or the like, and can also be used by impregnating a carrier such as a nonwoven fabric.

Examples 1-7, Comparative Examples 1-5
Acne improvers having the compositions shown in Table 1 were produced by the following method, and the melting point of the mixture of components (A) and (B) was measured, and the storage stability, acne improving effect and antibacterial effect were evaluated. The results are shown in Tables 1 and 2.

(Production method)
Components (6) to (17) are added to component (18) and stirred while heating at 80 ° C. Components (1) to (3) are dissolved in component (4) or (5), added to the aqueous solution, dispersed with a disper (1000 rpm), cooled to 25 ° C., defoamed, and adjusted to pH 4 to 5 Acne improving agent was obtained. In addition, when not containing a component (4) or (5), adding a component (1)-(3) and a component (6)-(17) to a component (18), heating at 80 degreeC. After stirring, the mixture was cooled to 25 ° C. and defoamed to obtain an acne improver having a pH of 4 to 5.

(Evaluation methods)
(1) Melting point of the mixture:
Component (1) and component (2) or component (1) and component (3) are mixed in the proportions used in each example, and the melting point of this mixture is determined using a differential calorimeter DSC6100 manufactured by Seiko Instruments Inc. And measured at a heating rate of 1 ° C./1 minute. An air-sealed sample was used as a standard product and the endothermic start temperature was defined as the melting point.

(2) Storage stability:
Each acne-improving agent was placed in a thermostatic bath at 50 ° C., 40 ° C., 25 ° C., 5 ° C., and −5 ° C., and the state after standing for 1 month was visually observed.
A: No change from immediately after.
○: Almost no change.
×: Immediately separated into two phases.

(3) Acne improvement effect:
For 20 healthy men aged 25 to 35 years with acne symptoms on the face, the acne-improving agent of the example or comparative example is applied to the right part of the face, and the control product is applied to the left part of the face twice a day in the morning and evening for 2 weeks. did. Thereafter, the improvement effect of the affected part of acne was determined by the following criteria by comparison with a control product. The result was shown by the average value of 20 people.
3 points; clearly improved compared to the control product.
2 points: Some improvement compared to the control product.
1 point: Slight improvement compared to the control product.
0 point: Not improved.

(4) Antibacterial effect:
Inoculate 0.01 mL of Acne bacteria (concentration 10 ⁶ / ml) (Propionibacterium acnes JCM 6425 ^T ) into 5 mL of each acne improver and maintain at 35 ° C. in an anaerobic culture tank for 15 minutes, 30 minutes, 60 minutes For 120 minutes. After culturing, 1 mL is taken from a test tube, diluted 10-fold with LP diluent (LP diluent “DAIGO” (manufactured by Nippon Pharmaceutical Co., Ltd .; Wako Pure Chemical Industries, Catalog No. 397-00281), Using the modified GAM agar medium (manufactured by Nippon Pharmaceutical Co., Ltd., product code 05420), the cells were cultured at 35 ° C. for 48 hours, and the number of remaining acne bacteria was measured.

Claims (3)

The following components (A), (B), (C) and (D):
(A) Sphingosines represented by the general formula (1)

(In the formula, R ¹ represents a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 4 to 30 carbon atoms, which may be substituted by a hydroxyl group, a carbonyl group or an amino group; A methylene group, a methine group or an oxygen atom; each of X ¹ , X ² and X ³ independently represents a hydrogen atom, a hydroxyl group or an acetoxy group, and X ⁴ represents a hydrogen atom, an acetyl group or a glyceryl group Together with an adjacent oxygen atom to form an oxo group (provided that when Y is a methine group, ^one of X ¹ and X ² is a hydrogen atom and the other does not exist. X ⁴ is an oxo group) when forming, X ³ is absent);. R ² and R ³ are each independently hydrogen atom, a hydroxyl group, a hydroxymethyl group or an acetoxymethyl group; a is a number of 2; a number of Each R is independently a hydrogen atom or amidino A linear or branched saturated or unsaturated hydrocarbon group having 1 to 8 carbon atoms which may have a substituent selected from a hydroxyl group, a hydroxyalkoxy group, an alkoxy group and an acetoxy group The broken line indicates that it may be an unsaturated bond),
(B) isopropylmethylphenol,
(C) polyol,
(D) The acne improving agent which contains water and the mass ratio of a component (A) and a component (B) is 0 <(B) / (A) <= 5.   The acne improving agent according to claim 1, further comprising (E) a cationic polymer or a cationic surfactant.   The acne-improving agent according to claim 1 or 2, further comprising (F) a polyether-modified silicone.