JP5063064B2 - Ceramide lipid dispersion - Google Patents

Description

  The present invention relates to a ceramide lipid dispersion in which ceramide lipids are stably blended and a cosmetic containing the same.

  Ceramide lipids typified by natural ceramides, sphingolipids, and ceramide analogs have excellent moisturizing effects and skin barrier functions, and thus are widely used in skin cosmetics and hair cosmetics (Patent Document 1).

However, ceramide lipids have high crystallinity and are difficult to dissolve or disperse. For example, crystals can be easily precipitated even if they are dissolved in a liquid oily component, resulting in sufficient penetration and fixation on the skin and hair. It is difficult to let In view of this, selection of a surfactant, selection of an oil agent, a production method, and the like have been studied in order to stably mix the composition. For example, a lactate or an alkylamphohydroxyalkyl sulfonate compound is used in combination as a surfactant (Patent Documents 2 and 3), and an alkyl lactate or alkenyl compound, or a fatty acid or aliphatic alcohol is used in combination as an oil agent (Patent Document 4). 5) Furthermore, ceramides, phospholipids and polyhydric alcohols are heated and mixed to form a lipid dispersion, and then water or the like is blended (Patent Document 6), or more than the melting point of ceramides and liquid oil. A method of mixing a polyglycerol fatty acid ester and an aqueous medium (Patent Document 7) has been performed.
Japanese Unexamined Patent Publication No. 63-192703 JP 2000-256188 A Japanese Patent Laid-Open No. 2004-196807 JP 2003-40728 A JP 2003-12486 A JP-A-11-130651 JP 2002-114631 A

However, in any method, the amount that exerts the effect of ceramide lipids cannot be blended, or even if blended, the problem of increased irritation to the skin due to the stability of the emulsion and the use of a surfactant, etc. was there.
Accordingly, an object of the present invention is to provide a technique capable of stably blending ceramide lipids by using a small amount of a surfactant.

  Therefore, the present inventors have made various studies and found that a stable ceramide lipid can be obtained by mixing a small amount of N-acyl-N-alkyltaurine or a salt thereof with ceramide lipids and glycerin and then dispersing the mixture in an aqueous phase. It has been found that a cosmetic dispersion having a low skin irritation in which ceramide lipids are stably blended can be obtained by mixing the dispersion with other components.

That is, the present invention contains (A) ceramide lipids, (B) N-acyl-N-alkyltaurine or a salt thereof and (C) glycerin, and the mass ratio of components (A) and (B) is (A ): (B) = 2: 1 to 14: 1, and the content of the component (C) is 70 to 99% by mass. A manufacturing method is provided.
The present invention also provides a ceramide lipid dispersion obtained by the above method and a cosmetic containing the dispersion.

  The ceramide lipid dispersion obtained by the method of the present invention exhibits excellent moisturizing effect and skin barrier function since ceramide lipids are stably dispersed. Moreover, since the amount of the surfactant used is small, the skin irritation is low. Therefore, the cosmetic containing the ceramide lipid dispersion of the present invention is a cosmetic for sensitive skin, for example, atopic skin, contact dermatitis, infants, dry skin, skin that is prone to troubles due to seasons, physical condition, stress, etc. It is particularly useful.

  In the method for producing a ceramide lipid dispersion of the present invention, first, a mixture containing (A) ceramide lipids, (B) N-acyl-N-alkyltaurine or a salt thereof and (C) glycerin is produced. The mixture is then dispersed in the aqueous phase. In the mixture of components (A) to (C), the mass ratio of (A) and (B) is (A) :( B) = 2: 1 to 14: 1. It is important for obtaining lipid dispersions. When (A) / (B) is less than 2, skin irritation due to component (B) occurs, and the stability of the dispersion also decreases. When (A) / (B) is greater than 14, a stable ceramide lipid dispersion cannot be obtained. The mass ratio of components (A) and (B) is more preferably 3: 1 to 10: 1 from the viewpoint of obtaining a stable dispersion.

  (A) Ceramide lipids include both natural ceramides and pseudo-ceramides, and are specifically represented by the following general formula (1).

(In the formula, R ¹ represents a linear, branched or cyclic saturated or unsaturated hydrocarbon group or hydrogen atom having 4 to 30 carbon atoms, which may be substituted by a hydroxyl group, a carbonyl group or an amino group. Z represents a methylene group, a methine group 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 a hydrogen atom, an acetyl group or a glyceryl group; or shown, together with the adjacent oxygen atom, forms an oxo group (provided that when Z is a methine group, either X ¹ and X ² is a hydrogen atom, is .X ⁴ the other is absent X ³ is not present when forming an oxo group.); R ² and R ³ each independently represent a hydrogen atom, a hydroxyl group, a hydroxymethyl group or an acetoxymethyl group; R ⁴ is a hydroxyl group, a carbonyl group or A A linear, branched or cyclic saturated or unsaturated hydrocarbon group having 5 to 60 carbon atoms which may have an ether bond, ester bond or amide bond in the main chain, which may be substituted by a mino group R ⁵ represents a hydrogen atom, or may have a substituent selected from a hydroxyl group, a hydroxyalkoxy group, an alkoxy group, and an acetoxy group, and is a linear or branched chain having 1 to 30 carbon atoms in total A saturated or unsaturated hydrocarbon group (provided that when R ¹ is a hydrogen atom and Z is an oxygen atom, R ⁵ is a hydrocarbon group having 10 to 30 carbon atoms in total, and R ¹ is a hydrocarbon group) ⁵ is a hydrocarbon group having 1 to 8 carbon atoms in total); the broken line indicates that it may be an unsaturated bond)

In the general formula (1), R ¹ may be substituted with a hydroxyl group, a carbonyl group or an amino group, and has 4 to 30 carbon atoms, preferably a hydroxyl group with 7 to 22 carbon atoms. A linear, branched or cyclic saturated or unsaturated hydrocarbon group or a hydrogen atom.
Z represents a methylene group, a methine group or an oxygen atom.

X ¹ , X ² and X ³ each independently represent a hydrogen atom, a hydroxyl group or an acetoxy group. In particular, 0 to ¹ of X ¹ , X ² and X ³ are preferably hydroxyl groups, and the remainder is preferably a hydrogen atom. When Z is a methine group, only ^one of X ¹ and X ² is a hydrogen atom, and the other does not exist. X ⁴ is preferably a hydrogen atom or a glyceryl group.
R ² and R ³ represent a hydrogen atom, a hydroxyl group, a hydroxymethyl group or an acetoxymethyl group, preferred R ² is a hydrogen atom or a hydroxymethyl group, and preferred R ³ is a hydrogen atom.

R ⁴ is a linear, branched or branched chain having 5 to 60 carbon atoms which may have an ether bond, an ester bond or an amide bond in the main chain, which may be substituted with a hydroxyl group, a carboxy group or an amino group. A cyclic saturated or unsaturated hydrocarbon group is shown. Preferably, the hydroxyl group or amino group may be substituted a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 5 to 35 carbon atoms, or a hydroxyl group at the ω position of the hydrocarbon group In which a linear, branched, or cyclic saturated or unsaturated fatty acid having 8 to 22 carbon atoms, which may be substituted, is an ester bond or an amide bond. As the fatty acid to be bonded, isostearic acid, 12-hydroxystearic acid or linoleic acid is preferable.

R ⁵ represents a hydrogen atom, or may have a substituent selected from a hydroxyl group, a hydroxyalkoxy group, an alkoxy group, and an acetoxy group. It is a saturated hydrocarbon group. When R ¹ is a hydrogen atom and Z is an oxygen atom, R ⁵ is a hydrocarbon group having 10 to 30 carbon atoms in total. When R ¹ is a hydrocarbon group, R ⁵ is a hydrocarbon group having 1 to 8 carbon atoms in total. Among these, a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms in which 1 to 3 groups selected from a hydroxyl group, a hydroxyalkoxy group and an alkoxy group may be substituted is preferable. Here, as a hydroxy alkoxy group and an alkoxy group, a C1-C7 thing is preferable.

The ceramides represented by the general formula (1) are particularly preferably ceramide lipids represented by the following general formula (2) or (3).
(I) Natural or natural ceramides represented by the general formula (2) and derivatives thereof (hereinafter referred to as natural ceramide).

(Wherein R ⁶ represents a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 7 to 19 carbon atoms which may be substituted by a hydroxyl group; Z ₁ represents a methylene group or a methine group; X ⁵ , X ⁶ and X ⁷ each independently represents a hydrogen atom, a hydroxyl group or an acetoxy group; X ⁸ represents a hydrogen atom or together with an adjacent oxygen atom, forms an oxo group. (However, when Z ₁ is a methine group, _one of X ⁵ and X ⁶ is a hydrogen atom and the other does not exist. When X ⁸ forms an oxo group, X ⁷ does not exist.); R ⁷ represents a hydroxymethyl group or an acetoxymethyl group; R ⁸ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R ⁹ has 5 to 30 carbon atoms which may be substituted by a hydroxyl group A linear, branched or cyclic saturated or unsaturated hydrocarbon group, Indicates an ester bond of a linear or branched saturated or unsaturated fatty acid having 8 to 22 carbon atoms which may be substituted with a hydroxyl group at the ω-terminal of the alkyl group; the broken line indicates an unsaturated bond Indicates that it may be.)

Preferably, R ⁶ is a linear alkyl group having 7 to 19 carbon atoms, more preferably 13 to 15 carbon atoms; R ⁹ is a linear alkyl group having 9 to 27 carbon atoms which may be substituted by a hydroxyl group, or linoleic acid Is a straight-chain alkyl group having 9 to 27 carbon atoms with an ester bond. X ⁸ preferably represents a hydrogen atom or forms an oxo group together with an oxygen atom. In particular, R ⁹ is preferably tricosyl, 1-hydroxypentadecyl, 1-hydroxytricosyl, heptadecyl, 1-hydroxyundecyl, or a nonacosyl group in which linoleic acid is ester-bonded to the ω position.

  Specific examples of natural ceramides include ceramide types 1 to 7 in which sphingosine, dihydrosphingosine, phytosphingosine or sphingadienin is amidated (for example, J. Lipid Res., 24: 759 (1983), FIG. And porcine and human ceramides described in FIG. 4 of J. Lipid. Res., 35: 2069 (1994)). Furthermore, these N-alkyl bodies (for example, N-methyl body) are also contained.

  These ceramides may be either natural (D (−)) optically active or non-natural (L (+)) optically active, or a mixture of natural and nonnatural. 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, compounds of CERAMIDE1, CERAMIDE2, CERAMIDE3, CERAMIDE5, CERAMIDE6II (above, INCI, 8th Edition) and those represented by the following formula are preferable.

The natural ceramide may be any of an extract from nature and a product obtained by chemical synthesis, and a commercially available product may be used.
Commercially available natural ceramides include Ceramide I, Ceramide III, Ceramide IIIA, Ceramide IIIB, Ceramide IIIC, Ceramide VI (Cosmo Farm), Ceramide TIC-001 (Takasago Inc.), CERAMIDE II (Quest International DS-Ceramide VI, DS-CLA-Phytoceramide, C6-Phytoceramide, DS-ceramide Y3S (DOOSAN), CERAMIDE2 (Cedera).

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

(In the formula, R ¹⁰ represents a linear, branched or cyclic saturated or unsaturated hydrocarbon group or a hydrogen atom having 10 to 22 carbon atoms which may be substituted by a hydroxyl group; X ⁹ represents a hydrogen atom; Acetyl group or glyceryl group; R ¹¹ is a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 5 to 22 carbon atoms which may be substituted with a hydroxyl group or an amino group, Or an ester bond of a linear or branched saturated or unsaturated fatty acid having 8 to 22 carbon atoms which may be substituted with a hydroxyl group at the ω-terminal of the hydrocarbon group; R ¹² represents a hydrogen atom Or a hydroxyl group, a hydroxyalkoxy group, an alkoxy group or an acetoxy group which may be substituted represents a C1-C30 alkyl group)

R ¹¹ is particularly nonyl, tridecyl, pentadecyl, an undecyl group in which linoleic acid is ester-bonded to the ω position, a pentadecyl group in which linoleic acid is ester-bonded to the ω position, and a pentadecyl group in which 12-hydroxystearic acid is ester-bonded to the ω position. An undecyl group in which methyl branched isostearic acid is amide-bonded at the ω position is preferred.

R ¹² is an alkyl having 10 to 30 carbon atoms, preferably 12 to 20 carbon atoms, which may be substituted with a hydroxyl group, hydroxyalkoxy group, alkoxy group or acetoxy group when R ¹⁰ is a hydrogen atom. A hydrogen atom when R ¹⁰ is a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 10 to 22 carbon atoms which may be substituted with a hydroxyl group, What shows a C1-C8 alkyl group which the hydroxyl group, the hydroxy alkoxy group, an alkoxy group, or an acetoxy group may substitute is preferable. The hydroxyalkoxy group or alkoxy group for R ¹² is preferably one having 1 to 7 carbon atoms.

In general formula (3), R ¹⁰ is a hexadecyl group, X ⁹ is a hydrogen atom, R ¹¹ is a pentadecyl group, and R ¹² is a hydroxyethyl group; R ¹⁰ is a hexadecyl group, X ⁹ is a hydrogen atom, and R ¹¹ is Preferred are pseudoceramides having a nonyl group, R ¹² is a hydroxyethyl group; or R ¹⁰ is a hexadecyl group, X ⁹ is a glyceryl group, R ¹¹ is a tridecyl group, and R ¹² is a 3-methoxypropyl group. It is particularly preferable that R ^{10 in} 3) is a hexadecyl group, X ⁹ is a hydrogen atom, R ¹¹ is a pentadecyl group, and R ¹² is a hydroxyethyl group.

  (B) The acyl group in N-acyl-N-alkyltaurine or a salt thereof includes a long-chain acyl group having 12 to 20 carbon atoms, and among these, an alkanoyl group, alkenoyl group, hydroxy group having 12 to 20 carbon atoms. Alkanoyl groups are preferred. Specific examples of the acyl group include lauroyl group, palmitoyl group, stearoyl group, oleoyl group, acyl group derived from coconut oil fatty acid (cocoyl group), and the like. Moreover, as an alkyl group, C1-C5 alkyl groups, such as a methyl group, an ethyl group, a propyl group, are mentioned, More preferably, it is a C1-C3 alkyl group. Examples of the salt of N-acyl-N-alkyltaurine include alkali metal salts such as sodium, potassium and lithium, and amine salts such as triethanolamine, diethanolamine and monoethanolamine.

  In the mixture containing the components (A) to (C), the content of the component (C) is 70 to 99% by mass, so that the dispersibility of the component (A) is high and a stable ceramide lipid dispersion is obtained. It is important to get. When the content of the component (C) is less than 70% by mass, a stable dispersion state of the component (A) cannot be obtained. Content of a component (C) is 70-99 mass% with respect to the mixture of a component (A)-(C), More preferably, it is 75-95 mass%. In addition, although a hydrate can also be used for glycerin, the moisture content is preferably 20% or less.

In the present invention, first, a mixture containing the above three components (A) ceramide lipids, (B) N-acyl-N-alkyltaurine or a salt thereof and (C) glycerin is produced, and the mixture is made into an aqueous phase. Obtained by dispersing. The mass ratio of the mixture to the aqueous phase is preferably 90:10 to 1:99, more preferably 60:40 to 1:99, and particularly preferably 30:70 to 3:97 from the viewpoint of the stability of the ceramide lipid dispersion. . The obtained ceramide lipid dispersion was liquid to paste.
In the aqueous phase of the present invention, organic acids, amino acids, preservatives, polyhydric alcohols, water-soluble polymers, anti-inflammatory agents, plant extracts, medicinal ingredients, humectants, polysaccharides, etc. can be used for cosmetics. A water-soluble component can be blended.

  The dispersion may contain an oily component other than ceramide lipids, for example, a solid, semi-solid, or liquid oily component at 25 ° C. Specifically, lipids such as cholesterols, C8 or higher fatty acids, phospholipids, sphingosines, sugar ceramides, and higher alcohols of C12 or higher can be blended.

In the present invention, when mixing the three components, that is, ceramide lipids, glycerin and taurine (salt) in the first stage, it is preferable not to add water. When glycerin is a hydrate, its moisture content is preferably 20% or less. After producing the mixture containing the three components, the mixture is dispersed in the aqueous phase. Even if the components (A), (B) and (C) are mixed with the aqueous phase at the same time, or after mixing any one or two of these three components with the aqueous phase, the other components are mixed. However, a ceramide lipid dispersion in which component (A) is stably dispersed cannot be obtained.
In addition, when mix | blending oily components other than ceramide lipids, after mix | blending the mixture of the said component (A)-(C) in an aqueous phase, disperse | distributing the liquid mixture containing another oily component to an aqueous phase. Thus, it can be simultaneously contained in the ceramide lipid dispersion. Further, in the ceramide lipid dispersion obtained by dispersing the mixed liquid (A) to (C) and the aqueous phase, the oil mixed with other oily components and, if necessary, a surfactant is dispersed. By adopting the production method, second oil droplet particles different from ceramide lipids can be contained.

  The mass ratio of components (A) and (B) in the ceramide lipid dispersion obtained by the present invention is the same as in the case of the above mixture. The content of the component (C) is 0.5 to 90% by mass as a result of dilution with the aqueous phase, more preferably 0.5 to 59% by mass, and particularly preferably 3 to 29% by mass. In addition, the content of the component (A) is preferably 0.0001 to 10% by mass, particularly preferably 0.1 to 7% by mass, from the viewpoint of the moisturizing effect, the skin barrier function and the stability. The content of the component (B) is preferably 0.00001 to 15% by mass, more preferably 0.0001 to 5% by mass, and particularly preferably 0.01 to 3% by mass from the viewpoint of skin irritation and stability.

  In the ceramide lipid dispersion obtained by the present invention, it is considered that (A) ceramide lipids are stably dispersed by forming fine dispersed particles. The presence of the finely dispersed particles can be confirmed with a polarizing microscope, a scanning microscope, or a transmission microscope. The particle diameter of the finely dispersed particles is about 100 nm to 10 μm. The particle diameter can be measured by a dynamic light scattering method or a laser diffraction / scattering method.

  In the obtained ceramide lipid dispersion, (A) ceramide lipids are stably dispersed, and thus have an excellent moisturizing effect and skin barrier function when applied to the skin, and have skin irritation. It is useful as a low and highly safe cosmetic. It is particularly useful as a skin cosmetic for sensitive skin, atopic dermatitis, contact dermatitis, infants, dry skin, and skin that is prone to troubles due to the season, physical condition and stress.

In addition to the ceramide lipid dispersion, the cosmetic of the present invention contains ingredients that can be used for cosmetics, for example, liquid oils other than lipids that can be incorporated into the dispersion, surfactants, and various medicinal ingredients. Can do. Examples of liquid oils include vegetable oils such as jojoba oil and olive oil, animal oils such as liquid lanolin, hydrocarbons such as squalene, squalane, liquid paraffin, liquid isoparaffin, cycloparaffin, isopropyl palmitate, isopropyl myristate, octyl myristate. Examples include esters such as dodecyl, hexyl laurate, cetyl lactate, propylene glycol monostearate, oleyl oleate, hexadecyl 2-ethylhexanoate, isononyl isononanoate, and tridecyl isononanoate. Further, as the surfactant, polyoxyethylene hydrogenated castor oil, glycerin fatty acid ester, polyoxyalkylene (C _{8 to} C ₂₀ ) fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene alkyl ether, monoalkyl glyceryl ether, Nonionic surfactants such as monoalkenyl glyceryl ethers and anionic surfactants such as higher fatty acid salts, sulfonic acid ester salts and alkyl phosphate esters are included. Examples of various medicinal ingredients include oil-soluble vitamin C, steroids, anti-inflammatory agents, antioxidants, antibacterial agents and the like.

Example 1
In the compound represented by the general formula (3), R ¹⁰ = C ₁₆ H ₃₃ , R ¹¹ = C ₁₅ H ₃₁ , R ¹² = H, X ⁹ = H (Sphingolipid E: Kao Corp.) 3 g, N- Stearoyl-N-methyltaurine sodium (Nikkor SMT: Nikko Chemicals Co., Ltd.) 0.5g and 86% glycerin (water mixing ratio 16.3% to glycerin) 16.5g were mixed and dissolved by heating at 85-88 ° C. A clear solution was obtained. To this, 80 g of water was added at 80 ° C. or higher, and the mixture was naturally cooled to room temperature while stirring with a propeller. The appearance of the obtained dispersion was translucent and slightly viscous. When the particle diameter was measured by a dynamic light scattering method, the mode particle diameter was 361.8 nm. Further, even when this dispersion was stored at 40 ° C. and −5 ° C. for 3 months, crystals were not precipitated and it was stable.

Comparative Example 1
In the compound represented by the general formula (3), R ¹⁰ = C ₁₆ H ₃₃ , R ¹¹ = C ₁₅ H ₃₁ , R ¹² = H, X ⁹ = H (Sphingolipid E: Kao Corp.) 3 g, N- Stearoylmethyl taurine sodium (Nikkor SMT: Nikko Chemicals Co., Ltd.) 0.5g and 86% glycerin (moisture mixing ratio 16.3% of glycerin) 5g were mixed and heated at 85-88 ° C. Without it, a turbid liquid was obtained. To this, 91.5 g of water was added at 80 ° C. or higher, and the mixture was naturally cooled to room temperature under propeller stirring. The appearance of the obtained dispersion was a liquid containing coarse aggregated precipitates. As a result of measurement with a polarizing microscope, many crystalline precipitates were observed.

Comparative Example 2
In the compound represented by the general formula (3), R ¹⁰ = C ₁₆ H ₃₃ , R ¹¹ = C ₁₅ H ₃₁ , R ¹² = H, X ⁹ = H (Sphingolipid E: Kao Corp.) 3 g, N- 2 g of sodium stearoylmethyl taurine (Nikkor SMT: Nikko Chemicals) and 16.5 g of 86% glycerin (water mixing ratio of 16.3% to glycerin) were mixed and dissolved at 85 to 88 ° C. to obtain a transparent solution. . To this, 78.5 g of water was added at 80 ° C. or higher, and the mixture was naturally cooled to room temperature under propeller stirring. The appearance of the obtained dispersion was a translucent liquid immediately after adjustment, and the mode particle diameter of the dynamic light scattering method was 94.1 nm, but many crystalline precipitates were observed over time.

Comparative Example 3
In the compound represented by the general formula (3), R ¹⁰ = C ₁₆ H ₃₃ , R ¹¹ = C ₁₅ H ₃₁ , R ¹² = H, X ⁹ = H (Sphingolipid E: Kao Corp.) 3 g, N- Stearoyl methyl taurine sodium (Nikkor SMT: Nikko Chemicals Co., Ltd.) 0.1g and 86% glycerin (moisture mixing ratio to glycerin 16.3%) 16.5g were mixed and heated at 85-88 ° C to make two phases. A separated solution was obtained. To this, 80.4 g of water was added at 80 ° C. or higher, and the mixture was naturally cooled to room temperature under propeller stirring. The appearance of the obtained dispersion was a liquid containing coarse aggregated precipitates.

Comparative Example 4
In the compound represented by the general formula (3), R ¹⁰ = C ₁₆ H ₃₃ , R ¹¹ = C ₁₅ H ₃₁ , R ¹² = H, X ⁹ = H (Sphingolipid E: Kao Corp.) 3 g, N- When 0.5 g of stearoylmethyl taurine sodium (Nikkor SMT: Nikko Chemicals Co., Ltd.) and 80 g of water were mixed at 85 to 88 ° C., a cloudy liquid was obtained. To this, 16.5 g of 86% glycerin (moisture mixing ratio with respect to glycerin 16.3%) was added at 80 ° C. or higher, and the mixture was naturally cooled to room temperature under propeller stirring. The appearance of the obtained dispersion was a liquid containing coarse aggregated precipitates.

Example 2
In the compound represented by the general formula (3), R ¹⁰ = C ₁₆ H ₃₃ , R ¹¹ = C ₁₅ H ₃₁ , R ¹² = H, X ⁹ = H (Sphingolipid E: Kao Corp.) 4.0 g, N-myristoylmethyl taurine sodium (Nikkor MMT: Nikko Chemicals Co., Ltd.) 0.8 g and 86% glycerin (water mixing ratio 16.3% to glycerin) 40 g were completely dissolved at 85 to 88 ° C. An aqueous phase containing 342.4 g of water, 12 g of 1,3-butylene glycol (1,3-butylene glycol P: Kyowa Hakko Chemical Co., Ltd.) and 0.8 g of methyl paraben (methyl paraoxybenzoate: API Corporation) Was added at 80-85 ° C. and stirred. The obtained dispersion was translucent, a fine dispersion having a mode particle diameter of 362.2 nm was formed, and no crystal precipitation was observed after storage at 40 ° C. and −5 ° C. for 3 months, and the dispersion was stable.

Example 3
In the compound represented by the general formula (3), R ¹⁰ = C ₁₆ H ₃₃ , R ¹¹ = C ₁₅ H ₃₁ , R ¹² = H, X ⁹ = H (Sphingolipid E: Kao Corp.) 4 g, N- 0.68 g of stearoylmethyl taurine sodium (Nikkor SMT: Nikko Chemicals Co., Ltd.) and 60 g of concentrated glycerin (water mixing ratio of 1.0% with respect to glycerin) were completely dissolved at 85 to 88 ° C. To this, an aqueous phase containing 2334.92 g of water and 0.4 g of methylparaben was added at 80 to 85 ° C. and stirred. The obtained dispersion was translucent, a fine dispersion having a dynamic light scattering mode particle size of 370.6 nm was formed, and no crystal deposition was observed after storage at 40 ° C. and −5 ° C. for 3 months. It was stable.

Example 4
In the compound represented by the general formula (3), R ¹⁰ = C ₁₆ H ₃₃ , R ¹¹ = C ₁₅ H ₃₁ , R ¹² = H, X ⁹ = H (Sphingolipid E: Kao Corp.) 6.75 g, 0.75 g of sodium N-stearoylmethyl taurine (Nikkor SMT: Nikko Chemicals Co., Ltd.) and 30 g of concentrated glycerin (water mixing ratio of 1.0% with respect to glycerin) were completely dissolved at 85 to 88 ° C. To this was added an aqueous phase containing 57.3 g of water, 5 g of 1,3-butylene glycol and 0.2 g of methylparaben at 80 to 85 ° C. and stirred. The obtained dispersion has a translucent paste-like appearance, contains fine particles having a mode particle diameter of 577.9 nm of dynamic light scattering method, and crystals are precipitated even after storage at 40 ° C. and −5 ° C. for 3 months. Was not seen and was stable.

Example 5
In the compound represented by the general formula (3), R ¹⁰ = C ₁₆ H ₃₃ , R ¹¹ = C ₁₅ H ₃₁ , R ¹² = H, X ⁹ = H (Sphingolipid E: Kao Corp.) 0.3 g, N-stearoylmethyl taurine sodium (Nikkor SMT: Nikko Chemicals Co., Ltd.) 0.15 g and concentrated glycerin (water mixing ratio 1.0% with respect to glycerin) 30 g were completely dissolved at 85 to 88 ° C. An aqueous phase containing 254.25 g of water, 15 g of 1,3-butylene glycol and 0.3 g of methylparaben was added thereto at 80 to 85 ° C. and stirred. The obtained dispersion has a translucent liquid appearance, contains fine particles with a mode particle diameter of 150.0 nm of the dynamic light scattering method, and crystals are precipitated even after storage at 40 ° C. and −5 ° C. for 3 months. Was not seen and was stable.

Example 6
2.4 g of commercially available natural ceramide (Ceramide IIIB: Cosmo Farm) represented by compound 4; 0.4 g of sodium N-stearoylmethyl taurine (Nikkor SMT: Nikko Chemicals Co., Ltd.) and 86% glycerin (moisture mixing with glycerin) 80 g (ratio 16.3%) were completely dissolved. To this was added an aqueous phase containing 316.4 g of water and 0.8 g of methylparaben at 80 to 85 ° C. and stirred. The obtained dispersion was translucent, contained fine particles with a mode particle diameter of 445.1 nm by dynamic light scattering method, and was stable after no storage of crystals after storage at 40 ° C. and −5 ° C. for 3 months. there were.

Example 7
4.0 g of commercially available natural ceramide (Ceramide III: Cosmo Farm) represented by Compound 4, 1.0 g of N-stearoylmethyl taurine sodium (Nikkor SMT: Nikko Chemicals Co., Ltd.) and 86% glycerin (moisture mixing with glycerin) 80 g (ratio 16.3%) were completely dissolved. To this was added an aqueous phase containing 294.2 g of water, 20 g of 1,3-butylene glycol and 0.8 g of methylparaben at 80 to 85 ° C. and stirred. The obtained dispersion was translucent, contained fine particles with a mode particle diameter of 417.5 nm by the dynamic light scattering method, had no crystal deposition even after storage at 40 ° C. and −5 ° C. for 3 months, and was stable. there were.

Example 8
In the compound represented by the general formula (3), R ¹⁰ = C ₁₆ H ₃₃ , R ¹¹ = C ₁₅ H ₃₁ , R ¹² = H, X ⁹ = H (Sphingolipid E: Kao Corp.) 4 g, N- Stearoyl methyl taurine sodium (Nikkor SMT: Nikko Chemicals Co., Ltd.) 0.68 g, cholesteryl isostearate (Exepal IS-CE: Kao Co., Ltd.) 0.4 g and 86% glycerin (water mixing ratio to glycerin 16.3%) 60 g was completely dissolved. To this, 311.88 g of water, 12 g of 1,3-butylene glycol, 0.8 g of methylparaben, 8 g of eucalyptus leaf extract (Falcolex Eucalyptus B: Ichimaru Falcos Co., Ltd.), alkyl methacrylate methacrylate copolymer (PEMULEN) TR-1: Noveon. Inc) 0.6 g, Arginine (Arginine: Ajinomoto Co., Inc.) 0.24 g, Hydroxypropylmethylcellulose (METROSE 60SH-4000: Shin-Etsu Chemical Co., Ltd.) 0.6 g, Allantoin (S-Allantoin) : Kawaken Fine Chemical Co., Ltd.) A water phase containing 0.8 g was added at 80 to 85 ° C. and stirred. The obtained dispersion has a translucent gel-like appearance, and is a fine dispersion having a mode particle diameter of 315.8 nm in a dynamic light scattering method, and after storage at 40 ° C. and −5 ° C. for 3 months. Precipitation of crystals was not seen and it was stable.

Example 9
Formula R ¹⁰ = C ₁₆ H ₃₃ with a compound represented by ^{(3), R 11 = C} 15 H 31, R 12 = H, X 9 = H ( sphingolipid E: Kao (Ltd.)) 6 g, N- Sodium stearoylmethyl taurine (Nikkor SMT: Nikko Chemicals Co., Ltd.) 0.8 g, cholesteryl isostearate (Exepal IS-CE: Kao Co., Ltd.) 0.8 g, and 86% glycerin (water mixing ratio to glycerin 16.3%) 60 g was completely dissolved. 314.36 g of water, 0.8 g of methylparaben, eucalyptus leaf extract (eucalyptus extract BG: Maruzen Pharmaceutical Co., Ltd.) 8 g, succinic acid (succinic acid SA Co., Ltd. Nippon Shokubai) 0.04 g, hydroxyethyl cellulose Sodium hydroxyethyl stearyl ether hydroxypropyl sulfonate (SPS-S-SA: Kao Corporation) 0.8 g, Carrageenan (Soagina MV101: MRC Polysaccharide Corporation) 0.4 g, Trimethylglycine (Amino Coat: Ajinomoto Co., Inc.) )) An aqueous phase containing 8 g was added at 80-85 ° C. and stirred. The obtained dispersion was a fine dispersion having a mode particle diameter of 360.3 nm and was stable with no crystal precipitation even after storage at 40 ° C. and −5 ° C. for 3 months. Further, it was slightly acidic at pH 4.8 and the appearance was a translucent gel.

Claims (7)

(A) General formula (1)
(In the formula, R ¹ represents a linear, branched or cyclic saturated or unsaturated hydrocarbon group or hydrogen atom having 4 to 30 carbon atoms, which may be substituted by a hydroxyl group, a carbonyl group or an amino group. Z represents a methylene group, a methine group 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 a hydrogen atom, an acetyl group or a glyceryl group; or shown, together with the adjacent oxygen atom, forms an oxo group (provided that when Z is a methine group, either X ¹ and X ² is a hydrogen atom, is .X ⁴ the other is absent X ³ is not present when forming an oxo group.); R ² and R ³ each independently represent a hydrogen atom, a hydroxyl group, a hydroxymethyl group or an acetoxymethyl group; R ⁴ is a hydroxyl group, a carbonyl group or A A linear, branched or cyclic saturated or unsaturated hydrocarbon group having 5 to 60 carbon atoms which may have an ether bond, ester bond or amide bond in the main chain, which may be substituted by a mino group R ⁵ represents a hydrogen atom, or may have a substituent selected from a hydroxyl group, a hydroxyalkoxy group, an alkoxy group, and an acetoxy group, and is a linear or branched chain having 1 to 30 carbon atoms in total A saturated or unsaturated hydrocarbon group (provided that when R ¹ is a hydrogen atom and Z is an oxygen atom, R ⁵ is a hydrocarbon group having 10 to 30 carbon atoms in total, and R ¹ is a hydrocarbon group) ⁵ is a hydrocarbon group having 1 to 8 carbon atoms in total); the broken line indicates that it may be an unsaturated bond)
In ceramide lipids represented, (B) containing N- acyl -N- alkyl taurine or a salt thereof and (C) glycerin, component (A) and the mass ratio of (B) is (A) :( B) = A method for producing a ceramide lipid dispersion, wherein a mixture of 2: 1 to 14: 1 and the content of the component (C) is 70 to 99% by mass is dispersed in an aqueous phase. Mass ratio of the mixture and the aqueous phase components (A) ~ (C) is 90: 10 to 1: preparation of ceramide lipids dispersion of claim 1 Symbol mounting 99. The method for producing a ceramide lipid dispersion according to claim 1 or 2 , wherein water is not blended when the three components (A) to (C) are mixed. The method for producing a ceramide lipid dispersion according to any one of claims 1 to 3 , wherein the content of the component (A) in the ceramide lipid dispersion is 0.0001 to 10% by mass. The method for producing a ceramide lipid dispersion according to any one of claims 1 to 4 , wherein the component (C) is glycerin having a water content of 20% or less. A ceramide lipid dispersion obtained by the method according to any one of claims 1 to 5 , wherein ceramide lipids are dispersed as finely dispersed particles of 100 nm to 10 µm . A cosmetic comprising the ceramide lipid dispersion according to claim 6 .