JP2001025654A - Surfactant aid - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a surfactant having high efficiency for increasing the solubilization capacity used in producing a microemulsion using a polyglycerin fatty acid ester, and a cosmetic, medicine and food using the same. provide. SOLUTION: When a microemulsion is produced using polyglycerin fatty acid ester, a surfactant aid containing sucrose fatty acid diester is used.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a surfactant used for producing a microemulsion using polyglycerol fatty acid ester. The microemulsion produced according to the present invention is used in a wide range of fields such as cosmetics, pharmaceuticals, foods and the like.

[0002]

BACKGROUND OF THE INVENTION Microemulsions are clear, homogeneous solutions containing two essentially immiscible liquids (eg, water and oil) and are generally obtained by gentle mixing of the components. In this regard, microemulsions are significantly different from macroemulsions which require vigorous stirring for their formation. The structure of the microemulsion changes from o / w type to b as the spontaneous curvature of the surfactant changes from positive to negative.
It changes to w / o type via iconinous structure. Water / Polyoxyethylene type nonionic surfactant /
In a microemulsion formed from an oil three-component system, such a structural change is observed due to a temperature change. The surfactant solubilizing capacity in this system is maximized at the temperature where the hydrophilic-hydrophobic balance (HLB) of the system is balanced, ie, at the HLB temperature. At the HLB temperature, the microemulsion has a bicontinuous structure, achieves an ultra-low interfacial tension, and allows approximately equal amounts of water and oil to mix and homogenize.

[0003] In order to increase the solubilizing capacity in a water / surfactant / oil system, an inorganic salt, a polyol having a salting-out effect on a hydrophilic chain such as a polyol, or an alcohol having a medium chain length and a relatively hydrophilic alcohol are used. It is known to use a surfactant (cosurfactant) such as a polyoxyethylene surfactant having a short group or a monoacylated glycerol. When a surfactant aid is used as an additive to increase the solubilizing capacity, a lipophilic surfactant aid is generally added to the hydrophilic ionic or nonionic surfactant. In this case, the HLB of the system changes greatly depending on the mixing ratio of the surfactant and the surfactant auxiliary,
As a result, the HLB temperature (the temperature at which the microemulsion is formed) also changes greatly. For this reason, there was a problem that the microemulsion was not generated at the temperature at which the microemulsion was assumed to be generated. In addition, the efficiency of increasing the solubilization capacity is correspondingly lower because such surfactants have very high monodisperse solubility in oil.

[0004]

As described above, the known surface-active aids greatly change the hydrophilic-hydrophobic balance (HLB) of the system, and increase the solubilization capacity because they are easily soluble in oil. However, there is a drawback that the efficiency of the process is low, so that it is necessary to use a large amount. Therefore, the system H
There has been a need for the development of additives that can increase the solubilization capacity with a small amount of addition without changing LB.

[0005]

The present inventors have made intensive studies to solve the above problems, and as a result, when producing a microemulsion using a polyglycerol fatty acid ester of a nonionic surfactant, sucrose was produced. When a fatty acid diester is used as a surfactant, the solubilizing capacity can be efficiently increased without greatly changing the HLB of the system and since the monodispersed concentration in the oil component is very low due to the strong hydrophilicity of the sucrose group. And found that the present invention can be increased. Furthermore, since sucrose fatty acid esters are excellent in biodegradability, there is also an advantage that the burden on the environment is small as compared with conventional surfactants.

That is, the gist of the present invention resides in a surfactant for producing a microemulsion using a polyglycerol fatty acid ester containing a sucrose fatty acid diester. Furthermore, a microemulsion containing a polyglycerin fatty acid ester and a sucrose fatty acid diester, and a cosmetic product comprising the microemulsion,
Present in medicines and foods.

[0007]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail. The microemulsion in the present invention is a homogeneous solution containing water and an oil component, and is an o / w type, bicontin.
There are uuous type and w / o type, and those having a micelle particle diameter of 100 nm to 10 μm in the case of o / w type or w / o type. In the present invention, in order to produce a microemulsion, a surfactant aid containing a sucrose fatty acid diester is used together with a polyglycerin fatty acid ester.

The constituent fatty acid species in the sucrose fatty acid diester contained in the surfactant aid of the present invention are those having 8 to 2 carbon atoms.
4, preferably 10-20, more preferably 12-18
Having a straight or branched chain, which is saturated or unsaturated. These fatty acids include lauric, myristic, palmitic, stearic, arachidic, behenic, tetradecenoic, hexadecenoic, octadecenoic, octadecadienoic, eicosenoic, eicosatetraenoic, docosenoic, Octadecatrienoic acid, isostearic acid and the like are mentioned, among which stearic acid and palmitic acid are preferable, and stearic acid is more preferable. These fatty acids can be used in combination of two or more kinds according to the purpose.

The surfactant aid of the present invention may contain, in addition to the sucrose fatty acid diester, sucrose fatty acid esters having different degrees of esterification, such as mono, tri and tetra. Usually, the sucrose fatty acid ester is often used as a mixture of each ester such as mono, di, and tri. In this case, the ratio of the sucrose fatty acid diester to the total amount of the sucrose fatty acid ester is 30% by weight or more. preferable.
If the content of the diester is lower than this range, the effect of increasing the solubilizing capacity is undesirably reduced.

The sucrose fatty acid diester of the present invention can be obtained, for example, by synthesizing a sucrose fatty acid ester by a known synthesis method and then obtaining a high-purity sucrose fatty acid ester by column chromatography (surfactant analysis method;
122, Koshobo).

The polyglycerin fatty acid ester used in the present invention is usually obtained by reacting polyglycerin with a fatty acid. The average degree of polymerization with polyglycerin is generally from 2 to 16, preferably from 4 to 12. The constituent fatty acids are generally selected from saturated or unsaturated fatty acids having 8 to 24 carbon atoms, preferably from 10 to 20,
More preferably, it is 12-18. These fatty acids include lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, tetradecenoic acid, hexadecenoic acid, octadecenoic acid, octadecadienoic acid,
Eicosenoic acid, eicosatetraenoic acid, docosenoic acid, octadecatrienoic acid, isostearic acid and the like,
Among them, lauric acid, myristic acid, palmitic acid and the like are preferable. These fatty acids can be used in combination of two or more kinds according to the purpose. Polyglycerin fatty acid esters are superior in safety compared to other nonionic surfactants such as polyoxyethylene alkyl ether, and are suitable for use in cosmetics, foods and drinks.

The microemulsion of the present invention comprises polyglycerin fatty acid ester, sucrose fatty acid diester,
It is obtained by mixing water and oily components. It can be manufactured by mixing each component at once, but beforehand, a surfactant mixture containing a surfactant aid consisting of polyglycerin fatty acid ester and sucrose fatty acid diester is manufactured, and this is added to a mixture of water and oily components. It can also be manufactured. The surfactant mixture in this case, from the viewpoint of improving the uniformity, a method of distilling off the solvent after dissolving a mixture of surfactants containing polyglycerin fatty acid ester and sucrose fatty acid diester in an organic solvent, and It is preferable to manufacture by mixing the two components at a temperature equal to or higher than the melting point.

As the oil component used in the present invention, liquid higher aliphatic hydrocarbons, animal and vegetable oils and fats, higher alcohols, higher fatty acids, synthetic ester oils, glycol higher fatty acid esters, silicone oils and the like are used. For example,
n-heptane, n-octane, n-decane, n-hexadecane, liquid paraffin, squalane, rapeseed oil, olive oil, castor oil, jojoba oil, octyldodecanol, octyldodecyl myristate, 2-ethylhexanoic triglyceride, capric triglyceride, Oleic alcohol, oleic acid and the like can be mentioned. These oil components can be used alone or in combination of two or more.

The polyglycerin fatty acid ester and the sucrose fatty acid diester in a surfactant mixture for producing a microemulsion containing a surfactant consisting of polyglycerin fatty acid ester and sucrose fatty acid diester are 99/1 to 50 by weight. / 50, preferably 95/5 to 60
/ 40, more preferably 90/10 to 70/30. When the content of the sucrose fatty acid diester is below this range, the effect of increasing the solubilizing capacity is reduced, and when the content is over this range, the mixture of sucrose fatty acid diester-polyglycerin fatty acid ester forms a liquid crystal to form a microemulsion. Becomes difficult.

In the microemulsion of the present invention,
The content by weight of the surfactant mixture, the oil component, and the water is generally 1 to 50%, 0.1 to 98.9%,
0.1 to 98.9%, and the type of the microemulsion may be any of o / w type, w / o type, and bicontinuous type. The content of the sucrose fatty acid diester relative to the total amount of the microemulsion of the present invention is generally 0.01 to 25% by weight, and the content of the polyglycerol fatty acid ester relative to the total amount of the microemulsion of the present invention is generally 0.5 to 25%. 49.5% by weight.

The microemulsion according to the present invention is used as cosmetics as detergents, shampoos, rinses, hair tonics, hair oils, hair lotions, aftershave lotions, body lotions, emollient oils, cosmetic lotions, cleansing oils, aerosol products, deodorants. It can be used as an agent, fragrance, deodorant, bath agent and the like. In addition, for pharmaceutical use, it can be used for oral administration preparations, external preparations for skin or mucous membrane application, injection preparations, drug delivery systems and the like.
Furthermore, for food applications, ice cream, coffee whitener, whipped cream, cheese, mayonnaise,
It can be used for dressings, whipped creams, sauces, sauces, coffee drinks, alcoholic drinks, milk drinks, solubilized oily flavors and the like. When used for these purposes,
The amount of the surfactant mixture containing the polyglycerin fatty acid ester and the sucrose fatty acid diester is generally 1 to 30% by weight based on the cosmetics, beverages and pharmaceuticals, and the amount of the sucrose fatty acid diester in the surfactant mixture is Generally, it is 1 to 50% by weight.

[0017]

EXAMPLES Hereinafter, the present invention will be further described with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof. [Production Example 1] Purification by sucrose stearic acid diester column chromatography In a mixed solvent of chloroform / methanol (8/2), sucrose stearic acid ester S-595 (Mitsubishi Chemical Corporation)
Was dissolved and added to silica gel packed in a column chromatography tube and eluted with a mixed solvent of chloroform / methanol (8/2). The diester fraction and the monoester fraction were concentrated. However, sucrose stearic acid diester having a purity of 100% was obtained.

[Production Example 2] Production example of polyglycerin laurate ester An improved simulated moving bed chromatographic separation apparatus was used from commercially available hexaglycerin (polyglycerin # 500; manufactured by Sakamoto Yakuhin Co., Ltd., average degree of polymerization: 5.9). As a result, polyglycerin from which components having a degree of polymerization of 7 or more were removed was prepared. The average degree of polymerization calculated from the hydroxyl value of this polyglycerin is 4.5.
Met. The fatty acid / polyglycerin reaction charge molar ratio was set to 1/1, and 156.4 g of this polyglycerin (0.4
Lauric acid (NAA-122; manufactured by NOF Corp., 99% by weight or more of lauric acid) and a 10% aqueous sodium hydroxide solution with an amount of sodium hydroxide of 0.006 mol.
It was charged so as to be 25 wt% (relative to the total amount), reacted at 240 ° C. and normal pressure under a nitrogen stream for 2.5 hours, heated to 260 ° C. and reacted for 4 hours to obtain polyglycerol laurate. Unreacted polyglycerin was removed from the polyglycerin laurate by liquid-liquid extraction to obtain a polyglycerin laurate having a residual polyglycerin content of 1% or less.

[Practical Examples 1 to 3] The polyglycerin laurate obtained in Production Example 2, the sucrose stearic acid diester obtained in Production Example 1, heptane, and distilled demineralized water were mixed at each mixing ratio. Then, the mixture was homogenized by heating and stirring and kept in a thermostat. The weight ratio of heptane to demineralized water was fixed at 1: 1. The presence or absence of phase separation at each mixing ratio and each temperature was confirmed, and the temperature (HLB temperature) at which a one-phase microemulsion was produced with the least amount of the surfactant mixture was confirmed. From the liquid composition at that time, the minimum surfactant mixture concentration (concentration of polyglycerin laurate ester + sucrose fatty acid ester) required to form a microemulsion was calculated. The weight ratio of the solubilized substance (heptane + demineralized water) to the surfactant mixture at that time was calculated. Table 1 shows the results.

Example 2 Commercially available sucrose stearic acid ester S-57 instead of sucrose stearic acid diester
Example 1 except that No. 0 (manufactured by Mitsubishi Chemical Corporation) was used.
The same was done. Sucrose stearic acid ester S-57
The composition of No. 0 is monoester / diester / triester / tetraester = 30/37/24/9, and the constituent fatty acids are stearic acid / palmitic acid = 70/30. Table 1 shows the results.

Comparative Example 1 The procedure of Example 1 was repeated except that no sucrose fatty acid diester was contained. Table 1 shows the results.

[0022]

[Table 1]

From the results of Example 1 and Comparative Example 1 (see Table 1), it was found that sucrose fatty acid diester was used as a surface-active aid against polyglycerin laurate (a nonionic surfactant). It can be seen that the concentration of the minimum surfactant mixture required to form a microemulsion is lower and the solubilization capacity is higher than when sucrose fatty acid monoester is used.

The results of Comparative Example 1 for Example 2 (Table 1)
), When sucrose fatty acid ester containing a large amount of sucrose fatty acid diester with respect to polyglycerin laurate ester (nonionic surfactant) was used as a surfactant aid, sucrose fatty acid diester was not used. It can be seen that the concentration of the minimum surfactant mixture required to form the microemulsion is lower and the solubilization capacity is higher than in the case.

[0025]

According to the present invention, when a microemulsion is produced using a polyglycerin fatty acid ester, the solubilization capacity can be efficiently increased without significantly changing the HLB of the system by using the surfactant aid containing the sucrose fatty acid diester of the present invention. Can be increased.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) A61K 9/107 A61K 9/107 47/14 47/14 47/26 47/26 47/34 47/34 B01F 17/42 B01F 17/42 B01J 13/00 B01J 13/00 A F term (reference) 4B026 DC06 DG01 DG11 DK01 DK03 DP01 DX04 DX05 4C076 AA17 DD46F DD68F EE23F FF16 4C083 AC421 AC422 AD221 AD222 BB02 BB04 A35 A04 AB35 A04A AB12 AC01 BA03 BA04 BA07 BA15 CA15 DC02Y DC16Z DC17Z DC22Z DC24Z DC34Y DC36Y DD04Y DD36Y DE02Y DE07Y DE08Y DE09Y DE13Y 4G065 AB05Y AB06Y AB12Y BA01 BB06 CA03 CA04 DA01 DA02

Claims (6)

[Claims] 1. A surfactant for producing a microemulsion using a polyglycerin fatty acid ester, comprising a sucrose fatty acid diester. 2. A surfactant mixture for producing a microemulsion, comprising a surfactant aid comprising a polyglycerin fatty acid ester and a sucrose fatty acid diester. 3. A microemulsion comprising a polyglycerin fatty acid ester and a sucrose fatty acid diester. 4. A cosmetic comprising the microemulsion according to claim 3. 5. A pharmaceutical comprising the microemulsion according to claim 3. 6. A food comprising the microemulsion according to claim 3.