JPH11199462A - Sphingolipid-surfactant complex - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject complex excellent in water dispersibility and capable of readily emulsifying and solubilizing by removing an organic solvent from an organic solvent solution in which sphingolipid, etc., and a surfactant are uniformly dissolved in the organic solvent to simultaneously deposit the sphingolipid and the surfactant. SOLUTION: This complex is obtained by removing an organic solvent from an organic solvent solution obtained by uniformly dissolving a sphingolipid (e.g. ceramide or cerebroside) or a substance having a structure analogous to the lipid and a surfactant into the organic solvent. The surfactant is preferably lecithin (e.g. soybean lecithin or yolk lecithin), a saccharide fatty acid ester (e.g. saccharide monoplamitate), a di-long chain alkyl quaternary ammonium salt type cation (e.g. distearyldimethyl ammonium chloride). The compounding ratio of the sphingolipid to the surfactant in the complex is preferably (1-70):(30-99) wt.%.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a sphingolipid-surfactant complex.

[0002]

2. Description of the Related Art It has recently been found that interstitial lipids have greatly contributed to the skin's water retention function, and it has been found that the skin's water retention function can be restored by supplying the extracellular lipids from the outside. It is becoming.

[0003] Sphingolipids are known lipids derived from naturally occurring epidermal cells. As one of the major components of epidermal keratinocytes, they greatly contribute to the function of retaining water in the skin. A method of applying the similar structural substance to the skin has been reported (Japanese Patent Publication No. 6-5).
No. 7651, Japanese Patent Publication No. 4-57641, and Japanese Patent Publication No. 4-59285).

[0004] Sterols are a group of compounds obtained from the unsaponifiable category when saponifying animal or plant fats and oils, and have recently attracted attention due to their physiological and pharmacological activities.
In particular, cholesterol is an essential component of keratinocyte intercellular lipid together with ceramide, and its importance in skin barrier function has been clarified. (R. Ghadially et al. J. Inves
tigative Dermatology, 106: 1064-1069 (1996))

As described above, cosmetics containing a sphingolipid such as ceramide and a lipid component originally present in the stratum corneum such as cholesterol and having a function of retaining moisture and a barrier function utilize the barrier function of the skin itself. It is an excellent cosmetic and has attracted attention in recent years.

However, these sphingolipids and sterols are high-melting compounds almost insoluble in water,
It is possible to emulsify both in an aqueous phase once they are dissolved in fats and oils, but it is generally difficult to obtain a stable emulsifying or solubilizing composition because of poor solubility in fats and oils, and sphingolipids When sterols are used in the form of a liquid or creamy preparation, there is a problem that the amount used is limited.

[0007]

The present invention relates to a sphingolipid-surfactant complex or a sphingolipid-sterol complex which can be easily dispersed in water or fat to obtain a stable emulsified or solubilized composition. It is intended to provide a complex of the active agent.

[0008]

Means for Solving the Problems Under such circumstances, the present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, it has been found that sphingolipids and surfactants or sphingolipids, sterols and surfactants are contained in an organic solvent. The sphingolipid and the surfactant or the sphingolipid, the sterol and the surfactant are simultaneously precipitated by removing the organic solvent from the organic solvent liquid uniformly dissolved in
Surfactant complex or sphingolipid-sterol-
A surfactant complex was formed, which was found to be excellent in water dispersibility and easily emulsified or solubilized.

Furthermore, it has been found that when this composite is blended, a cosmetic having an excellent moisturizing effect and a good feeling upon use can be obtained.

In the present invention, the complex refers to a complex in which a mixture of a plurality of substances does not show individual physicochemical properties of a single substance but shows one physicochemical property as a complex. For example, the behavior with respect to temperature is changed by the complexation, and the solubility and dispersibility in a solvent are improved.

The complex of the present invention can be obtained by simultaneously precipitating all components from an organic solvent solution in which sphingolipid and a surfactant or sphingolipid, sterol and a surfactant are uniformly dissolved. To simultaneously precipitate sphingolipids and surfactants or sphingolipids and sterols and surfactants, for example, distilling off the organic solvent from the organic solvent solution under heating and reduced pressure, or It can be performed by spray drying to remove the organic solvent. In the spray drying, the organic solvent solution is supplied to a tubular heater at a constant speed, and heated in the heater to evaporate the organic solvent to substantially form a mixture of solids and vapor of the organic solvent. The mixture can be introduced by introducing the mixture into a vacuum chamber at high speed and evaporating the organic solvent instantaneously. This method is described in JP-B-4-1491.
No. 94 is described.

Alternatively, the method can be carried out by instantly freezing the above organic solvent solution with liquid nitrogen or the like and then removing the organic solvent by freeze-drying.

According to the above method, a complex is formed without a chemical reaction between sphingolipid and a surfactant or between sphingolipid, a sterol and a surfactant.

The remarkable effect of the complex of the sphingolipid and the surfactant or the sphingolipid and the sterol and the surfactant of the present invention is that the sphingolipid and the surfactant or the sphingolipid and the sterol and the surfactant are simply mixed. You can't get it.

[0015] The present invention provides a sphingolipid-surfactant complex, a sphingolipid-sterol-surfactant complex, and a cosmetic containing the complex.

That is, the present invention provides the following items 1 to 7.

Item 1. A sphingolipid obtained by removing an organic solvent from an organic solvent solution in which a sphingolipid or a similar structural substance and a surfactant are uniformly dissolved in the organic solvent to simultaneously precipitate the sphingolipid and the surfactant,
Surfactant complex.

Item 2. The sphingolipid, sterol and surfactant were obtained by simultaneously removing the organic solvent from the organic solvent solution in which sphingolipid or its similar structural substance, sterol and surfactant were uniformly dissolved in the organic solvent Sphingolipid-sterol-surfactant conjugate.

Item 3. Item 1. A sphingolipid-surfactant complex and a sphingolipid-sterol-surfactant complex, wherein the surfactant of claim 1 or 2 is lecithin.

Item 4. Item 7. A sphingolipid-surfactant complex and a sphingolipid-sterol-surfactant complex, wherein the surfactant of items 1 and 2 is a sucrose fatty acid ester.

Item 5. Item 7. A sphingolipid-surfactant complex and a sphingolipid-sterol-surfactant complex, wherein the surfactant of item 1 or 2 is a dilong chain alkyl quaternary ammonium salt type cation.

Item 6. Item 6. A cosmetic containing the composite according to item 1, 2, 3, 4 or 5.

Item 7. Item 7. A therapeutic agent for a skin disease caused by desiccation, comprising the complex according to Item 1, 2, 3, 4 or 5.

[0024]

BEST MODE FOR CARRYING OUT THE INVENTION As sphingolipids used in the present invention, cerebroside is used in addition to ceramide.

Ceramide is a known compound having the general structure (1), and can be obtained from the epidermis of mammals such as humans, pigs, cows, horses and sheep by a usual extraction method.

In addition, Japanese Patent Application Laid-Open No. 61-271205 and a biochemistry experiment book (Lipid Chemistry, Biochemistry Experiment Course, Vol. 3,
Ceramide obtained by the production method described in pages 20 to 21, 1974, edited by The Biochemical Society of Japan, Tokyo Kagaku Dojin) may be used.

[0027]

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The sphingolipid-like structural substance has two long-chain hydrocarbon groups, an OH group and an amide group between them, and the molecule takes a one-dimensional conformation. Refers to lipid derivatives that can be used.

Examples of such similar structural substances include amide derivatives represented by the following general structure (2).

[0030]

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The production method of this amide derivative is described in Japanese Patent Publication No. 59259/1992.

The cerebroside used in the present invention is a complex lipid obtained by adding a sugar to the ceramide of the above structure (1), and is a known compound represented by the general structure (3). This cerebroside can be obtained by extraction or synthesis from the epidermis of mammals such as humans, pigs, cows, horses and sheep.

[0033]

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These sphingolipids or structural substances similar thereto may be used alone or as a mixture of two or more.

The sterol of the present invention is not particularly limited as long as it is an alcohol having a steroid skeleton. For example, sterols derived from animals such as cholesterol, dihydrocholesterol, lanosterol, dihydrolanosterol, desmosterol, and stigmasterol, Examples include plant-derived sterols (phytosterols) such as sitosterol, campesterol and brassicasterol, and microorganism-derived sterols such as ergosterol, and preferably cholesterol and phytosterol. These sterols may be used alone or as a mixture of two or more.

The surfactant used in the present invention is not particularly limited as long as it is generally used in cosmetics.
Among them, lecithin, sucrose fatty acid ester or dilong chain alkyl quaternary ammonium salt type cation is particularly preferable.

The lecithin used in the present invention includes, for example, natural lecithin such as soybean lecithin and egg yolk lecithin;
These lecithin hydrogenated products can be exemplified.

The sucrose fatty acid ester used in the present invention is an ester of sucrose and a saturated or unsaturated fatty acid having 10 to 24 carbon atoms, which is limited by the degree of substitution of hydroxyl groups in sucrose (esterification degree). However, it may be a monoester, a diester, or a tri- or higher ester. Alternatively, a mixture of sucrose fatty acid esters having different esterification degrees may be used.

Examples of fatty acids constituting such sucrose fatty acid esters include caproic acid, caprylic acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, arachidic acid, behenic acid, zomaric acid, lignoceric acid, Cellotic acid, oleic acid, elaidic acid,
Linoleic acid, linolenic acid, arachidonic acid, eicosapentaenoic acid, docosapentaenoic acid, docosahexaenoic acid,
Such sucrose fatty acid esters include, for example, sucrose fatty acid monoesters represented by sucrose monopalmitate, sucrose monostearate, sucrose monooleate, etc., for example, sucrose Dipalmitate, sucrose distearate, sucrose fatty acid diester represented by sucrose dioleate and the like, for example, sucrose tripalmitate, sucrose tristearate, sucrose fatty acid triester represented by sucrose trioleate and the like, and Mixtures and the like can be mentioned.

The dilong chain alkyl quaternary ammonium salt type cation used in the present invention is represented by the following general structure (4).

[0041]

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Representative examples include distearyldimethylammonium chloride, dipalmityldimethylammonium chloride, dieicosyldimethylammonium chloride, dipheneicosyldimethylammonium chloride, didocosyldimethylammonium chloride, didocosyldiethylammonium chloride, Dicosyleicosyl dimethyl ammonium chloride,
Examples include di-hardened tallow alkyldimethyl ammonium chloride and di-hardened tallow alkyl dimethyl ammonium bromide.

The mixing ratio of sphingolipid to surfactant in the sphingolipid-surfactant complex of the present invention is 0.1.
The content is preferably about 01 to 99: 1 to 99.99% by weight. Preferably, the content is about 1 to 70:30 to 99% by weight.

The sphingolipid, sterol and sterol in the sphingolipid-sterol-surfactant complex of the present invention
The compounding ratio of the surfactant is 0.01 to 99: 0.01 to 9
9: 0.99 to 99.98% by weight.
Preferably, the content is about 1 to 70: 1 to 70:50 to 98% by weight.

The organic solvent for dissolving the above-mentioned sphingolipid or its similar structural substance, sterol and surfactant may be any one which can simultaneously dissolve any of sphingolipid or its similar structural substance, sterol and surfactant. It is not particularly limited. Specifically, for example, pentane, hexane, heptane, hydrocarbons such as cyclohexane, methylene chloride, halogenated hydrocarbons such as chloroform, benzene, aromatic hydrocarbons such as toluene, methanol, ethanol, butanol and the like Examples thereof include lower alcohols and esters such as methyl acetate and ethyl acetate. The amount of the organic solvent to be used is not particularly limited, and may be appropriately selected from a wide range according to the solubility of sphingolipid or a similar structural substance thereof, sterol, lecithin or sucrose fatty acid ester. Taking into account, the total amount of sphingolipids or similar structural substances, sterols and surfactants used is 1 to 1
It is preferably about 00 times by weight, preferably about 3 to 50 times by weight.

The sphingolipid-surfactant complex and the sphingolipid-sterol-surfactant complex of the present invention can be produced, for example, as follows.

First, sphingolipids, surfactants or sphingolipids, sterols, and surfactants are dissolved in the above organic solvent. At this time, if means such as heating and stirring are used, the efficiency is further improved.

The resulting solution is spray-dried using a spray-drying apparatus such as a two-fluid type or a disk type, preferably a solvent-recovering type, to obtain the desired sphingolipid-surfactant complex or sphingolipid-sterol. The surfactant complex can be obtained in powder, oil and semi-solid form; Generally, a homogeneous mixture obtained in powder form is desirable from the viewpoint of swelling speed.

The amount of the sphingolipid-surfactant complex or the sphingolipid-cholesterol-surfactant complex in the cosmetic of the present invention is not particularly limited.
About 01-99% is preferable. Further, the cosmetic of the present invention may contain water, alcohols, oil components, surfactants, phospholipids, whitening components, ultraviolet absorbers, polymer substances, preservatives, fragrances, pigments, and the like. In addition, other moisturizing components such as keratinocyte intercellular lipids, polyhydric alcohols, hyaluronic acid, and lactic acid bacteria culture solution can be added.

The remedy for skin diseases caused by drying of the skin is applied directly to the skin in the form of ointments, patches, lotions, liniments, liquid coatings and the like. The compounding amount of the complex of the present invention is 0.01 to 99% by weight for each dosage form.
It is about. As for the ingredients such as ointments, patches, lotions, liniments, liquid coatings, etc., all additives usually used in these preparations can be used.

[0051]

Next, the features of the present invention will be described in detail with reference to examples, but the present invention is not limited to these examples.

Production Example 1 Ceramide containing 90% or more of N-stearoylphytosphingosine (manufactured by Nikko Chemicals Co., Ltd., melting point 129)
C) 1 g and 4 g of hydrogenated soybean lecithin (manufactured by Trulecithin Industry Co., Ltd.) containing 30% of phosphatidylcholine, 25% of phosphatidylethanolamine and 20% of phosphatidylinositol in 20 mL of tertiary butanol, and then dissolved in liquid nitrogen. Freezes instantaneously and freeze-drying equipment Flexi-Dry (FTS SYSTEMS, INC.)
Was freeze-dried. The pressure was 200 millitorr or less, and the trap temperature was -80 ° C. The ceramide-lecithin complex of the present invention thus obtained was a homogeneous white powder.

The complex obtained in Production Example 1, the ceramide and hydrogenated soybean lecithin used in Production Example 1, and further the Production Example 1
FIG. 1 shows a DSC (differential scanning calorimetry) chart of a simple mixture of 1 part by weight of the ceramide used in Example 1 and 4 parts by weight of hydrogenated soybean lecithin. FIG. 1 shows that the composite of the present invention does not show an endothermic peak corresponding to the melting of the raw material ceramide and the phase inversion of lecithin, but shows a new endothermic peak and forms a composite.

[0054]

FIG.

On the other hand, a simple mixture of ceramide and hydrogenated soybean lecithin shows an endothermic peak corresponding to melting of ceramide and phase inversion of lecithin, and no complex is formed.

When the obtained complex was separated by a silica gel column, ceramide and hydrogenated soybean lecithin were obtained in a weight ratio of ceramide: hydrogenated soybean lecithin = 1: 4, and other eluted substances were observed. Ceramide and hydrogenated soybean lecithin were not chemically reacted.

As described above, the composite of the present invention is characterized in that the physical properties are changed without involving a chemical reaction.

Production Example 2 Hydrogenated soybean lecithin (True) containing 3 g of ceramide containing 90% or more of N-stearoylphytosphingosine (manufactured by Nikko Chemicals Co., Ltd.), 30% of phosphatidylcholine, 25% of phosphatidylethanolamine and 20% of phosphatidylinositol. Lecithin Industry Co., Ltd.) 7
g was dissolved in 200 mL of chloroform, and then spray-dried (Tokyo Rika Kikai Co., Ltd., Spray dryer S)
D-1). Spray air pressure is 1.5kg
/ Cm 2, the liquid feed rate was 5 g / min, the chamber inlet temperature was 65 ° C., and the outlet temperature was 40 ° C. The ceramide-lecithin complex of the present invention thus obtained was a homogeneous white powder.

Production Example 3 2.4 g of ceramide containing 90% or more of N-stearoyl phytosphingosine (manufactured by Nikko Chemicals Co., Ltd.) and a sucrose fatty acid ester (Ryoto Sugar Ester S-5)
70, manufactured by Mitsubishi Chemical Foods Corporation, monoester content 30
%, HLB5, constituent fatty acid composition is about 70 stearic acid
%) Of 7.6 g was dissolved in 200 mL of chloroform, and then spray-dried with a spray-drying apparatus (manufactured by Tokyo Rika Kikai Co., Ltd., spray dryer SD-1). The spray air pressure was 1.5 kg / cm 2, the liquid sending rate was 5 g / min, the chamber inlet temperature was 65 ° C, and the outlet temperature was 40 ° C. The ceramide-sucrose fatty acid ester complex of the present invention thus obtained was a homogeneous white powder.

Production Example 4 1.0 g of ceramide containing 90% or more of N-stearoyl phytosphingosine (manufactured by Nikko Chemicals Co., Ltd.) and 9.0 g of distearyldimethylammonium chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) in 200 mL of chloroform And spray-dried with a spray dryer (manufactured by Tokyo Rika Kikai Co., Ltd., spray dryer SD-1). The spray air pressure was 1.5 kg / cm 2, the liquid sending rate was 5 g / min, the chamber inlet temperature was 65 ° C, and the outlet temperature was 40 ° C. The ceramide-distearyldimethylammonium chloride complex of the present invention thus obtained was a homogeneous white powder.

Production Example 5 2 g of ceramide containing 90% or more of N-stearoyl phytosphingosine (manufactured by Nikko Chemicals Co., Ltd.), 4 g of cholesterol (manufactured by Nippon Seika Co., Ltd.), 30% of phosphatidylcholine, 25% of phosphatidylethanolamine and 25% of phosphatidyl After dissolving 4 g of hydrogenated soybean lecithin containing 20% of inositol (manufactured by True Lecithin Industry Co., Ltd.) in 200 mL of chloroform, a spray drying apparatus (manufactured by Tokyo Rika Kikai Co., Ltd., spray dryer SD-1 type)
And spray dried. The spray air pressure is 1.5kg / cm2,
The liquid sending rate was 5 g / min, the chamber inlet temperature was 65 ° C, and the outlet temperature was 40 ° C. The ceramide-cholesterol-lecithin complex of the present invention thus obtained was a homogeneous white powder.

Production Example 6 1.5 g of ceramide (manufactured by Nikko Chemicals Co., Ltd.) containing 90% or more of N-stearoyl phytosphingosine, 0.5 g of cholesterol (manufactured by Nippon Seika Co., Ltd.) and sucrose fatty acid ester (Ryoto) Sugar ester S-570,
Manufactured by Mitsubishi Chemical Foods Corporation, monoester content 30%, H
LB5, constituent fatty acid composition is about 70% stearic acid) 8g
Is dissolved in 200 mL of chloroform, and then spray-dried (spray dryer SD, manufactured by Tokyo Rika Kikai Co., Ltd.).
(Type-1). The spray air pressure is 1.5kg /
cm 2, liquid feed rate 5 g / min, chamber inlet temperature 6
The outlet temperature was 5 ° C and the outlet temperature was 40 ° C. The ceramide-cholesterol-sucrose fatty acid ester complex of the present invention thus obtained was a homogeneous white powder.

Production Example 7 1.0 g of ceramide (manufactured by Nikko Chemicals Co., Ltd.) containing 90% or more of N-stearoyl phytosphingosine, 1.0 g of cholesterol (manufactured by Nippon Seika Co., Ltd.) and distearyl dimethyl ammonium chloride (Tokyo, Japan) Chemical Industry Co., Ltd.)
After dissolving 8.0 g in chloroform 200, the mixture was spray-dried with a spray dryer (manufactured by Tokyo Rika Kikai Co., Ltd., spray dryer SD-1). Spray air pressure is 1.5
kg / cm 2, the liquid sending rate was 5 g / min, the chamber inlet temperature was 65 ° C., and the outlet temperature was 40 ° C. The ceramide-cholesterol-distearyldimethylammonium chloride complex of the present invention thus obtained was a homogeneous white powder.

Example 1 0.2 g of each of the composites obtained in Production Examples 1 to 7 was
The mixture was added to 100 mL of warm water at 80 ° C, and dispersed with Hiscotron (manufactured by Nichion Medical Science Instrument Co., Ltd.) (80 ° C, 20000 r)
pm, 20 minutes) and then cooled to room temperature. The dispersion state of these dispersions is stably maintained for a long time,
No precipitate was formed in a standing stability test at 30 ° C. for 30 days.

Comparative Example 1 Hydrogenated soybean lecithin containing 0.06 g of ceramide (manufactured by Nikko Chemicals Co., Ltd.) containing 90% or more of N-stearoylphytosphingosine, 30% of phosphatidylcholine, 25% of phosphatidylethanolamine and 20% of phosphatidylinositol. (True Lecithin Industry Co., Ltd.
0.14 g) was added to 100 mL of hot water at 80 ° C.
After dispersing (80 ° C., 20,000 rpm, 20 minutes) with Hiscotron (manufactured by Nichion Medical Science Instrument Co., Ltd.), the mixture was cooled to room temperature. A precipitate was present in the obtained liquid and did not become a good dispersion.

Comparative Example 2 0.048 g of ceramide (manufactured by Nikko Chemicals Co., Ltd.) containing 90% or more of N-stearoyl phytosphingosine and sucrose fatty acid ester (Ryoto Sugar Ester S)
-570, manufactured by Mitsubishi Chemical Foods Co., Ltd., monoester content 30%, HLB5, constituent fatty acid composition is about 7 stearic acids
(0%) was added to 100 mL of hot water at 80 ° C., dispersed with Hiscotron (manufactured by Nichion Medical Science Instruments Co., Ltd.) (80 ° C., 20,000 rpm, 20 minutes), and then cooled to room temperature. A precipitate was present in the obtained liquid and did not become a good dispersion.

COMPARATIVE EXAMPLE 3 0.02 g of ceramide (manufactured by Nikko Chemicals Co., Ltd.) containing 90% or more of N-stearoylphytosphingosine and 0.16 g of distearyldimethylammonium chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) at 80 ° C. To 100 mL of warm water, and Hiscotron (manufactured by Nichion Medical Science Instrument Co., Ltd.)
(80 ° C., 20,000 rpm, 20 minutes), and then cooled to room temperature. A precipitate was present in the obtained liquid and did not become a good dispersion.

Comparative Example 4 0.04 g of ceramide (manufactured by Nikko Chemicals Co., Ltd.) containing 90% or more of N-stearoyl phytosphingosine, 0.08 g of cholesterol (manufactured by Nippon Seika Co., Ltd.), 30% of phosphatidylcholine, and phosphatidylethanolamine Hydrogenated soybean lecithin containing 25% and phosphatidylinositol 20% (manufactured by True Lecithin Industry Co., Ltd.)
0.08 g was added to 100 mL of hot water at 80 ° C., and dispersed with Hiscotron (manufactured by Nichion Medical Science Instrument Co., Ltd.) (8
(0 ° C., 20,000 rpm, 20 minutes), and then cooled to room temperature. A precipitate was present in the obtained liquid and did not become a good dispersion.

Comparative Example 5 0.03 g of ceramide (manufactured by Nikko Chemicals Co., Ltd.) containing 90% or more of N-stearoyl phytosphingosine, 0.01 g of cholesterol (manufactured by Nippon Seika) and sucrose fatty acid ester (Ryoto) Sugar ester S-57
0, manufactured by Mitsubishi Chemical Foods Co., Ltd., monoester content 30
%, HLB5, constituent fatty acid composition is about 70 stearic acid
%) And 0.16 g to 100 mL of 80 ° C. hot water,
After dispersing (80 ° C., 20,000 rpm, 20 minutes) with Hiscotron (manufactured by Nichion Medical Science Instrument Co., Ltd.), the mixture was cooled to room temperature. A precipitate was present in the obtained liquid and did not become a good dispersion.

Comparative Example 6 0.02 g of ceramide (manufactured by Nikko Chemicals Co., Ltd.) containing 90% or more of N-stearoyl phytosphingosine, 0.02 g of cholesterol (manufactured by Nippon Seika Co., Ltd.) and distearyl dimethyl ammonium chloride (Tokyo, Japan) Chemical Industry Co., Ltd.
0.16 g) was added to 100 mL of hot water at 80 ° C.
After dispersing (80 ° C., 20,000 rpm, 20 minutes) with Hiscotron (manufactured by Nichion Medical Science Instrument Co., Ltd.), the mixture was cooled to room temperature. A precipitate was present in the obtained liquid and did not become a good dispersion.

From the results of Example 1 and Comparative Examples 1 to 6, it is clear that the composite of the present invention produces a very stable dispersion.

Example 2 Preparation of Moisture Cream Ingredient Ratio (% by Weight) Oil Phase Component: Vitamin E Acetate 0.2 Shortening Oil 5.0 Beeswax 1.0 Squalane 5.6 Olive Oil 10.0 Ceramide of Production Example 4 Cholesterol-lecithin complex 5.0 Aqueous phase component: Glycerin 5.0 Methylparaben 0.1 Ethylparaben 0.1 Perfume Appropriate amount Purified water Amount based on 100

The oil phase component in the above formulation is heated and stirred to be uniform and kept at 70 ° C. Purified water and glycerin are heated and agitated, and a mixture made uniform at 70 ° C. is gradually added, and emulsified by an emulsifier. The emulsion was cooled to 30 ° C. with a heat exchanger to prepare a moisture cream.

Comparative Example 7 1.0 weight of ceramide (manufactured by Nikko Chemicals Co., Ltd.) containing 90% or more of N-stearoyl phytosphingosine instead of the ceramide-cholesterol-lecithin complex (5% by weight) of Example 2. %, Cholesterol (manufactured by Nippon Seika Co., Ltd.) 2.0% by weight and phosphatidylcholine 30
%, Hydrogenated soybean lecithin containing 25% phosphatidylethanolamine and 20% phosphatidylinositol (manufactured by True Lecithin Industry Co., Ltd.) in the same manner as in Example 2, except that 2.0% by weight was used. did.

Example 3 Preparation of Lotion Ingredient Ratio (% by Weight) Complex of Ceramide-Cholesterol-Sucrose Fatty Acid Ester of Production Example 5.0 5.0 Dimethylpolysiloxane 5.0 Cetyl 2-ethylhexanoate 2.0 Methylparaben 0.1 Polyethylene glycol 3.0 1,3-butylene glycol 5.0 Perfume Appropriate amount Purified water Amount based on 100

The dimethylpolysiloxane in the above formula, 2
Heating and stirring the cetyl ethylhexanoate, ceramide-cholesterol-sucrose fatty acid ester complex, methylparaben, and flavor to make them uniform; Then, purified water, polyethylene glycol, and 1,3-butylene glycol kept at 70 ° C. are heated and stirred, and a mixture made uniform at 70 ° C. is gradually added, and emulsified by an emulsifier. The emulsion was cooled to 30 ° C. with a heat exchanger to prepare a lotion.

Comparative Example 8 Ceramide (manufactured by Nikko Chemicals Co., Ltd.) containing 90% or more of N-stearoyl phytosphingosine instead of the ceramide-cholesterol-sucrose fatty acid ester complex (5% by weight) of Example 3 0.75% by weight, cholesterol (manufactured by Nippon Seika Co., Ltd.) 0.25% by weight and sucrose fatty acid ester (Ryoto Sugar Ester S-570, manufactured by Mitsubishi Chemical Foods, Inc., monoester content 30%, HL)
B5, constituent fatty acid composition is about 70% of stearic acid) 4.0
A lotion was prepared in the same manner as in Example 3 except that the weight% was used.

Example 4 Preparation of Hair Conditioner Ingredient Ratio (% by Weight) A Component Ceramide-cholesterol-distearyldimethylammonium chloride complex of Production Example 2.0 behenyl alcohol 8.0 lanolin 1.0 2-octyldodecanol 6.0 Cetyl isooctanoate 4.0 Polyoxyethylene (7) oleyl ether 2.0 B component 1,3-butylene glycol 12.0 Preservative / bactericidal agent Appropriate amount Purified water 100 parts C component Perfume / pigment Appropriate amount

After dissolving the component A at 70 ° C. and mixing with stirring, the component B previously dissolved and mixed at 70 ° C. is added and mixed with stirring. Then, add the C component and stir and mix.
After cooling to 0 ° C., a hair conditioner was prepared.

Comparative Example 9 In place of the ceramide-cholesterol-distearyldimethylammonium chloride complex (2% by weight) of Example 4,
0.2% by weight of ceramide (manufactured by Nikko Chemicals Co., Ltd.) containing 90% or more of N-stearoyl phytosphingosine;
A hair conditioner was prepared in the same manner as in Example 4, except that 0.2% by weight of cholesterol (manufactured by Nippon Seika Co., Ltd.) and 1.6% by weight of distearyldimethylammonium chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) were used. Was prepared.

Test Example 1 In order to check the stability of the emulsions of Examples 2, 3 and 4, and Comparative Examples 7, 8 and 9, the stability at 40 ° C. was examined.
Table 1 shows the results.

As shown in Table 1, the stability of the emulsions of Examples 2, 3 and 4 was better than those of Comparative Examples 7, 8 and 9. In the evaluation column of Table 1, "
””: Stable 10 days after the preparation of the emulsion.

"△": A precipitate was formed 1 to 9 days after the preparation of the emulsion.

"X": A precipitate was formed within one day after the preparation of the emulsion.

[0085]

[Table 1]

Test Example 2 Examples 2 and 3 and Comparative Examples 7 and 8 were given to 10 female panelists.
The cosmetics prepared in the above were actually used and evaluated for practical use. The evaluations were (1) stretching at the time of application, (2) familiarity with the skin, and (3)
The following evaluation criteria were used for six items: moist feeling after application, (4) stickiness, (5) skin moistness three hours after application, and (6) overall evaluation. The results are shown in Table 2. In Table 2, “２”: 8 or more out of 10 responded that they were good.

"O": 6 or more out of 10 answered that they were good.

"△": 4 or more out of 10 answered that they were good.

“×”: Less than 4 out of 10 responded that it was good.

[0090]

[Table 2]

Table 2 shows that the cosmetic of the present invention is very excellent in the feeling of use.

Test Example 3 The inside of the forearm of 10 female panelists was used as a measurement site, and defatted with 10 ml of acetone: diethyl ether (1: 1, volume) for 30 minutes using a cup, and then prepared in Examples 2 and 3. The applied cosmetic was applied. The application was started before going to bed on the day of the degreasing treatment, and thereafter, every day after getting up and before going to bed. Before defatting, after defatting, and after application, the keratin water content and transepidermal water loss were measured using an impedance meter (manufactured by IBS) and a tevameter (manufactured by C & K), respectively. The measurement was performed after the measurement site was washed with hot water at 37 ° C. and the panel was adapted to an environment of 20 ° C. and 50% humidity for 20 minutes or more.
Tables 3 and 4 show the obtained results. Values are averages (n =
10).

[0093]

[Table 3]

[0094]

[Table 4]

Tables 3 and 4 show that the cosmetics prepared in Examples 2 and 3 have an excellent improvement effect on the dry and rough skin induced by removing lipids in the stratum corneum by solvent treatment. This indicates that the composition is useful as a skin cosmetic and a therapeutic agent for skin diseases.

Test Example 4 Ten female panelists actually used the hair conditioners prepared in Example 4 and Comparative Example 9 to evaluate practical use. The evaluation was the overall feeling of use, and the results are shown in Table 5. In Table 5, "表": 8 or more out of 10 responded that they were good.

"O": 6 or more out of 10 answered that they were good.

"△": 4 or more out of 10 answered that they were good.

"X": Less than 4 out of 10 respondents answered "good".

[0100]

[Table 5]

As described above, the hair conditioner of the present invention obtained in Example 4 had a good feeling in use.

[Procedure amendment]

[Submission date] March 18, 1998

[Procedure amendment 1]

[Document name to be amended] Statement

[Correction target item name] Brief description of drawings

[Correction method] Added

[Correction contents]

[Brief description of the drawings]

FIG. 1 is a DSC (differential scanning calorimetry) chart. Ceramide used in Production Example 1, hydrogenated soybean lecithin, a simple mixture of 1 part of ceramide and 4 parts of hydrogenated soybean lecithin, and the invention of Production Example 1 Each composite was subjected to a thermal measurement by DSC. Downward peaks indicate endothermic phenomena such as melting and phase transition.

[Description of Signs] mW on the vertical axis is a unit of heat (milliwatt). Minus represents endotherm.

Claims (7)

[Claims] 1. A sphingolipid or a surfactant obtained by removing an organic solvent from an organic solvent solution in which a sphingolipid or a similar structural substance and a surfactant are uniformly dissolved in the organic solvent to simultaneously precipitate the sphingolipid and the surfactant. Sphingolipid-surfactant complex. 2. The sphingolipid, the sterol and the surfactant are simultaneously precipitated by removing the organic solvent from the organic solvent solution in which the sphingolipid or a similar structural substance, the sterol and the surfactant are uniformly dissolved in the organic solvent. A sphingolipid-sterol-surfactant complex obtained at least. 3. A sphingolipid-surfactant complex and a sphingolipid-sterol-surfactant complex wherein the surfactant of claim 1 and 2 is lecithin. 4. A sphingolipid-surfactant complex and a sphingolipid-sterol-surfactant complex wherein the surfactant of claim 1 or 2 is a sucrose fatty acid ester. 5. A sphingolipid-surfactant complex and a sphingolipid-sterol-surfactant complex wherein the surfactant of claim 1 or 2 is a dilong chain alkyl quaternary ammonium salt type cation. 6. A cosmetic containing the complex according to claim 1, 2, 3, 4 or 5. 7. A therapeutic agent for a skin disease caused by desiccation, comprising the complex according to claim 1, 2, 3, 4, or 5.