JP2837305B2 - Stabilizer - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a sterol derivative, more particularly, O-glucosyl, O-glucosyl, glycerol having phytosterol, cholesterol, cholestanol, lanosterol or 2,4-dihydrolanosterol.
- a maltosyl or O- galactosyl each derivative is concerned the use as stabilizers for various surface phenomena.

[0002]

2. Description of the Related Art In general, a surfactant is used to obtain a homogeneous state of two or more components which are not mixed. For example,
When mixing a hydrophobic organic phase and the aqueous phase or hydrophilic materials, utilizing an emulsion technique or solubilization techniques. In the case of a powder and an aqueous phase or an organic phase , a dispersion treatment is performed.

[0003] emulsion, lysates, the dispersion is used in such fields as pharmaceuticals, cosmetics, toiletries and foods, polyhydric alcohol derivatives as surfactants for this, ether compounds, fatty acid soaps, alkyl phosphate Derivatives, alkyl sulfonic acid derivatives, amino acid derivatives and the like are widely used. Usually, surfactants are properly used depending on physical properties such as required HLB, dielectric constant, and dipole moment of a hydrophobic substance.

Usually, these interfacial phenomena often cause separation or the like after long-term storage. Therefore, polyhydric alcohols such as glycerin, waxes, and sterols are added to stabilize the system. These additives have the effect of enhancing the storage stability of the system, enhancing the function of the surfactant, and reducing the amount of the surfactant used.

[0005]

However, these existing stabilizers have insufficient long-term stabilizing effects on interfacial phenomena such as emulsification, solubilization, and dispersion, and have a higher stabilizing effect. Is required. In addition, the surfactants and substrates to be mixed with each stabilizer are limited, and usable systems are also limited. Therefore, an object of the present invention is to provide a stabilizing agent for various interfacial phenomena having a high stabilizing action in a wide range of systems and interface states.

[0006]

Means for Solving the Problems The present inventors have conducted intensive studies, glucoside specific sterols, when used maltoside or galactoside each derivative was found ability to impart stabilization of excellent interfacial phenomena. The present invention has been completed based on this finding, and has the following general formula (1)
And a surfactant comprising one or more of sterol glucoside, sterol maltoside or sterol galactoside as a component.

[0007]

Embedded image

Glucosyl and maltosyl used in the present invention
Or galactosyl each derivative, using natural extracts or synthetic distributed in the plant kingdom, such as soybeans. As a synthesis method,
Generally, a method of synthesizing an alkyl glucoside may be used. That is, a method of directly reacting sterol with sugar, a method of reacting sterol with acetylated sugar and then deacetylating, a method of reacting sterol with halogenated sugar and the like can be mentioned.

[0009] thus obtained glucosyl, a maltosyl or galactosyl each derivative was added to the surfactant, conventional components, by appropriately blending the optional ingredients, it can be prepared a homogeneous composition such as emulsion-lysate . The blending amount cannot be specified unconditionally, but in general, when used as a stabilizer, it is preferably 0.01 to 60% of the total amount or 10 to 0.1 times the surfactant amount. When it is lower than this range, the stabilizing effect is small, and when it is larger, the solubility and the like are inferior.

[0010] The glucosyl, since maltosyl or galactosyl each derivative is superior to the stabilization of the various surfactants, emulsifiers alone or in combination with other various surface active agents, solubilizing agents, dispersing agents, liposomal It can be incorporated into the agent, and as a result, the total amount of other surfactants to be added can be reduced. Examples are shown below, but these examples do not limit the application of the present invention.

[0011]

EXAMPLES Example 1 23.3 g of cholesterol in 300 ml of dichloromethane,
24.0 g of glucose pentaacetate and 10.0 g of anhydrous iron (III) chloride are added. Stir overnight at room temperature,
The dichloromethane solution was washed with a saturated aqueous sodium hydrogen carbonate solution. After washing with water, it was concentrated. 2 g of sodium methoxide and 200 ml of ethanol were added to the concentrate, which was refluxed for 6 hours and concentrated. Wash the concentrate with water,
After drying, the residue was purified by column chromatography to obtain 5 g of cholesterol glucoside. In addition, other derivatives according to the present invention used in the following examples were prepared in the same manner.

Example 2 Emulsion stabilization test: Sodium caseinate was dissolved in distilled water, and cholesterol or a derivative thereof was mixed with liquid paraffin. The results obtained by mixing and emulsifying the aqueous phase and the organic phase are shown in Table 1. As apparent from Table 1, glucosyl, maltosyl and galactosyl each derivative of the present invention have excellent emulsion stability.

[0013]

[Table 1]

Example 3 Emulsion stabilization test: After adding cholesterol or a derivative thereof to a nonionic surfactant adjusted to HLB 10.5, dissolving it in liquid paraffin, emulsifying in distilled water, the results are shown in Table 2. It was shown to. As is clear from Table 2,
Glucosyl derivatives have excellent emulsion stability.

[0015]

[Table 2]

Example 4 Solubilization test: Tocopherol was added with sucrose monostearate and glycerin, glycosyl derivative or galactosyl derivative, and dissolved in ethanol to prepare a sample. Table 3 shows the amount of water that the sample can solubilize. As is clear from Table 3, glucosyl derivatives and galactosyl derivatives have excellent solubilization stability.

[0017]

[Table 3]

Example 5 Dispersibility test: After a surfactant and a curcosyl derivative were dissolved in ether and titanium oxide was dispersed, the ether was distilled off. Table 4 shows the results of dispersing this sample in liquid paraffin.

[0019]

[Table 4]

Example 6 Stabilization test of liposome: Liposomes were prepared by adding cholesterol, cholesterol glucoside or lanosterol maltoside to hydrogenated lecithin, and adding dipropylene glycol and distilled water. Table 5 shows the stability results. As is evident from Table 5, liposomes containing sterol glucoside or lanosterol maltoside have excellent stability.

[0021]

[Table 5]

Example 7 Mayonnaise was prepared in accordance with a conventional method according to the formulation shown in Table 6. No separation was observed after storage at 30 ° C. for one month.

[0023]

[Table 6]

Example 8 A shampoo was prepared in accordance with a conventional method according to the formulation shown in Table 7. A shampoo with good lather was obtained.

[0025]

[Table 7]

Example 9 A lipstick was prepared according to the formulation shown in Table 8 according to a conventional method. The pigment was well dispersed and a lipstick without perspiration was obtained.

[0027]

[Table 8]

Example 10 A cream was prepared according to a conventional method according to the formulation shown in Table 9.
Even when the obtained cream was stored at 30 ° C. for 6 months, no separation was observed.

[0029]

[Table 9]

Example 11 An ointment was prepared according to the formulation shown in Table 10 according to a conventional method. Even when the obtained ointment was stored at 30 ° C. for 6 months, no separation was observed.

[0031]

[Table 10]

[0032]

Glucosyl, maltosyl and galactosyl each derivative of the present invention exhibits, because of its excellent stabilization of various surfactants, stable emulsions can be obtained lysate, the dispersions and liposomes, It can be incorporated into various emulsifiers, solubilizers, dispersants, and liposome bases. In addition, it has properties that can be used for foods, cosmetics, external preparations, pharmaceuticals and the like.

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Claims (5)

(57) [Claims] 1. One or more of 1-O-sterol glucoside, 1-O-sterol maltoside or 1-O-sterol galactoside represented by the general formula (1) is a constituent component. Interfacial stabilizer. Embedded image 2. The stabilizer according to claim 1, which is incorporated into an emulsion. 3. The method according to claim 1 , wherein the compound is added to a solubilized substance.
The stabilizer as described. 4. The stabilizer according to claim 1, which is incorporated into a dispersion. 5. The stabilizer according to claim 1, which is incorporated into a liposome.