JPH09315932A - Solubilizing agent and cosmetic containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a solubilizing agent useful in the medicinal and cosmetic fields, containing a branched aliphatic polyglycoside having a specific average polymerization degree. SOLUTION: This solubilizing agent contains a branched aliphatic polyglycoside of the formula Gn-O-R (Gn is a residue formed by eliminating glycosidic hydroxyl groups from a product formed by dehydrocondensation of monosaccharide G and having a polymerization degree of (n); (n) is an integer of >=1; R is an 8-32C branched aliphatic chain as a result of forming glycoside linkage to Gn) with an average polymerization degree of >=2.1. If being <2.1 in the average polymerization degree, this solubilizing agent is inadequate in function as such, while if >=2.1, this agent presents excellent safety, stability and solubilizing ability, having favorable use feeling when applied to the skin. A skin cosmetic or hair cosmetic can be prepared by formulating 0.5-60wt.% of this solubilizing agent in the corresponding cosmetic base.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a solubilizing agent, particularly a solubilizing agent containing a branched aliphatic polyglycoside.

[0002]

2. Description of the Related Art Solubilizing agents are widely used in the fields of pharmaceuticals and cosmetics. Typical solubilizers are nonionic surfactants, for example, glycerin fatty acid ester, sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycol fatty acid ester, polyoxyethylene alkyl ether. , Polyoxyethylene alkyl phenyl ether, polyoxyethylene hydrogenated castor oil derivative, mannitol hydroxy fatty acid ester and the like.

[0003]

When such a solubilizing agent is used in pharmaceuticals and cosmetics, it has a good solubilizing ability and, in addition, it is required to have high safety for use in the human body. It is also desirable that the stability is excellent. However, recently, problems have been pointed out regarding the safety and stability of nonionic surfactants.

For example, a compound having an ester portion is liable to undergo hydrolysis and has a problem in stability, and a compound having a polyoxyethylene chain as a hydrophilic group is apt to undergo oxidative deterioration with the passage of time, resulting in a low molecular weight aldehyde. It also has problems with stability and safety, such as the generation of organic acids and organic acids, which may cause odor and irritation. Although the glycerin derivative has good stability and safety, there is a problem in that the degree of polymerization of glycerin is not easily increased due to synthesis and the hydrophilicity is poor.

Further, the amount of solubilization naturally depends on the amount of the solubilizing agent, but in the case of a surfactant, its HLB is used.
As a result, the amount of solubilization changes remarkably, and in the case of solubilizing oil, for example, the amount of solubilization also greatly changes depending on the structure of the oil. That is, in order to obtain an optimum solubilized state, it is necessary that the oil content to be solubilized matches the HLB of the solubilizing agent and its structure. It will lead to more possibilities.

There are also maltitol fatty acid hydroxyethers which are excellent in safety and stability, but those external preparations for skin which are prone to foam during use are not preferred. From the above, it has been desired to develop a novel solubilizing agent which can satisfy all of safety, stability, usability and solubilizing ability. The present invention has been made in view of the problems of the prior art as described above, and an object thereof is a novel solubilizing agent capable of satisfying all of safety, stability, usability and solubilizing ability. And to provide a cosmetic containing the same.

[0007]

Means for Solving the Problems As a result of intensive studies to achieve the above-mentioned objects, the present inventors have found that
The present invention has been completed by finding that a branched aliphatic polyglycoside, which has been known as a highly stable thickening gelling agent, functions as a solubilizing agent when it has a specific average degree of polymerization. That is, the present invention contains a branched aliphatic polyglycoside represented by the general formula 2, and the average degree of polymerization of the branched aliphatic polyglycoside is 2.1 or more, and a solubilizing agent, The present invention relates to cosmetics containing the same.

[0008]

Embedded image In the formula, Gn means a residue obtained by removing a glycosidic hydroxyl group from a monosaccharide G dehydrated and condensed at a degree of polymerization of n.
n is an integer of 1 or more. Further, R means a branched fatty chain having a glycoside bond with Gn and having a total carbon number of 8 to 32. )

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION Embodiments of the present invention will be described in detail below. In the general formula 2, Gn is a monosaccharide G
Represents a residue obtained by removing a glycosidic hydroxyl group from a product dehydrated and condensed at a polymerization degree of n. Specific examples of the monosaccharide G include monosaccharides such as glucose, galactose, xylose, fructose, altrose, talose, mannose, arabinose, idose, lyxose, ribose and allose, and mixtures thereof. The degree of polymerization n is an integer of 1 or more. When n is 1, the monosaccharide is not dehydrated and condensed, and only one monosaccharide is R-glycoside-bonded.

Next, R is a branched fatty chain linked to Gn by a glycosidic bond and has a total carbon number of 8 to 32. Specific examples of the branched chain include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group,
Decyl group, undecyl group, dodecyl group, tridecyl group,
Examples thereof include a tetradecyl group, a heptadecyl group, a hexadecyl group, a heptadecyl group, and further higher fatty chains. The position and number of such branched chains are not particularly limited. Specific examples of R include 2-decyltetradecyl group, 2-tetradecyloctadecyl group, isostearyl group, 2,7-dimethylhexadecyl group, tetrahydrageranyl group, and 2,7-dimethyloctadecyl group. . R is a hydrophobic group, and the total number of carbon atoms is preferably 8 to 32 from the viewpoint of balance and industrial property.

The branched aliphatic polyglycoside according to the present invention can be obtained by a dehydration condensation reaction of a branched aliphatic alcohol and a sugar, a method of using an acid catalyst for saccharide modification described in JP-A-63-84637, and generally glycosyl. The compound can be synthesized by the reaction used for the compound (König-Knol reaction, Helferreich method, other ether exchange method, etc.).

During the steps of these synthetic reactions, sugars used as raw materials are polymerized with each other, and thus the obtained branched aliphatic polyglycoside is usually obtained as a mixture having different degrees of polymerization of sugars and different bonding positions of sugars. In the present invention, even such a mixture can be used as it is when the average degree of polymerization of the branched aliphatic polyglycoside is 2.1 or more. Of course, as long as it has the average degree of polymerization of the branched aliphatic polyglycoside which is a feature of the present invention, the mixture may be appropriately purified and used as a highly pure branched aliphatic polyglycoside, or they may be re-prepared. You may use it.

The branched aliphatic polyglycoside constituting the solubilizer of the present invention is known as a substance, and has been excellent in stability and safety up to now, has gelling ability, and functions as an emulsion stabilizer. It was known to have the following (Japanese Patent Application Laid-Open No. 4-76082, Japanese Patent Application Laid-Open No. 4-89494). However, it has not been known so far that such a branched aliphatic polyglycoside exerts a function as a solubilizing agent depending on its average degree of polymerization, and it has been clarified for the first time by the present invention.

The solubilizer of the present invention contains the branched aliphatic polyglycoside of the above formula 2 and has an average degree of polymerization of 2.1.
It is necessary to be above. When the average degree of polymerization is less than 2.1, the function as a solubilizing agent is not sufficiently exhibited. The solubilizer of the present invention is oily or solid at room temperature, becomes a transparent solution when dissolved in water, and has less foaming than existing nonionic surfactants. In the case of a branched aliphatic polyglycoside having an average degree of polymerization of less than 2.1, when it is dissolved in water, a thickening gelling ability is exerted to increase the viscosity of the system, and the viscosity depends on the concentration of the branched aliphatic polyglycoside. In contrast to rising. Further, the solubilizer of the present invention has a good feeling of use when applied to the skin or hair, and a moisturizing feeling of use can be obtained.

Due to the above properties, the solubilizing agent of the present invention can be blended in various cosmetics for hair such as shampoo, rinse, treatment, hair styling agent, hair dye, color rinse in addition to skin cosmetics. Further, it can be applied to medicines and is expected to be used in various industrial fields that require other solubilizers.

The amount of the solubilizer according to the present invention to be added to the cosmetic of the present invention is not particularly limited as long as the effects of the present invention can be obtained, and the amount of the solubilizer to be added depends on the component to be solubilized and its amount. The amount can be appropriately adjusted and used, but it is generally 0.5 to 60% by weight. Further, in the cosmetic of the present invention, in addition to the branched aliphatic polyglycoside as a solubilizer, other components usually used in cosmetics can be appropriately blended unless the effects of the present invention are impaired.

For example, liquid paraffin, squalane, petrolatum, cetyl alcohol, isostearyl alcohol, 2-ethylhexyl alcohol, cetyl-2-octyldodecyl alcohol 2-ethylhexanoate, glyceryl triisostearate, macadamian nut oil, lanolin, etc. Various hydrocarbons, oils and fats, oil components such as waxes, silicones, other surfactants, thickeners, neutralizers,
Preservative, bactericide, antioxidant, powder component, pigment, fragrance,
Examples thereof include, but are not limited to, ultraviolet absorbers, medicinal agents, sequestering agents, pH adjusting agents and the like.

Further, known components usually used in hair dyes, such as oxidation dyes, acid dyes, various alcohols,
Organic solvents, pH adjusters, inorganic acids, humectants, oily ingredients, sequestering agents, preservatives, cationic polymers, pH adjusters, fragrances, drugs, water, other amphiphilic substances and surfactants , Thickeners, protein hydrolysates and their tetrachlorides,
Antioxidants, stabilizers, alkaline agents, oxidizing agents and the like can also be added. Embodiments of the present invention will be described below.
The case where R is an isostearyl group and G is glucose in the above chemical formula 2 is further detailed as an example.

First, a method for producing isostearyl polyglucoside will be described. Production Example 1 Isostearyl polyglucoside Isostearyl alcohol 10.05 g (378 mmol)
Glucose (40.5 g, 225 mmol) and paratoluenesulfonic acid (0.19 g, 1 mmol) were added thereto, and the mixture was reacted for 16 hours under reduced pressure with introduction of nitrogen while stirring. The reaction product was cooled to room temperature, and purified water, ethyl acetate, and methanol were added to the reaction system for partition. The aqueous layer was concentrated, and the obtained syrup was washed with acetone to obtain isostearyl polyglucoside. The average degree of polymerization of glucose in the obtained isostearyl polyglucoside was 25
Trimethylchlorosilane (0.5 ml), N, O- (bistrimethylsilyl) acetamide (0.5 ml) and N-trimethylsilylimidazole (0.5 ml) were added to mg, and TMS was formed on a hot water bath at 80 ° C for 30 minutes, followed by capillary gas chromatography (Cardrex Aluminum Super capped column (methyl silicone 1 μm × 10 m) Split ratio 1/20, heating rate 100-420 ° C., 10 ° C. /
min, carrier gas: helium, 50 ml / min,
The average degree of polymerization of glucose was 2.4 as determined from the peak area intensity by a detector: FID).

Production Example 2 Isostearyl monoglucoside
Production of isostearyl alcohol 10.05g (378mmo
l), 2 g of pentaacetyl glucose and 10 mg of phosphomolybdic acid were added with 20 ml of toluene, heated to 90 ° C., and then heated and stirred for 30 minutes under a reduced pressure of 20 mmHg. After cooling with air, the mixture was extracted with toluene, filtered, washed once with saturated saline and purified water, dried and concentrated under reduced pressure. The obtained syrup was purified by a silica gel chromatogram method (Wako Gel C-200, hexane / ethyl acetate) to obtain an acetylated product of isostearyl monoglucoside. The obtained acetylated product was dissolved in methanol, sodium methylate was added, and the mixture was stirred at room temperature for 30 minutes to deacetylate it. After the reaction, the resin (Amberlite 120
After neutralizing with B) and filtering off the resin, the obtained filtrate was concentrated to obtain the desired isostearyl monoglucoside.

Test Example 1 Solubilizing ability Isostearyl polyglucosides having various average degrees of polymerization were prepared and their solubilizing ability was investigated. As a method, a 2% aqueous solution of isostearyl polyglucoside was prepared, 0.5 g of limonene was added dropwise to the aqueous solution with stirring, and the solution stirred for 7 days was observed for its properties and appearance and its viscosity was measured. The average degree of polymerization of isostearyl polyglucoside was adjusted by adding the isostearyl monoglucoside obtained in Production Example 2 to the isostearyl polyglucoside having an average degree of polymerization of 2.4 prepared in Production Example 1. The viscosity was measured using an E-type viscometer (VISCONIC ED, manufactured by Tokimec Co., Ltd.) under the conditions of a temperature of 25 ° C. and a cone rotor of 0.5 rpm.

The properties and the presence or absence of separation of the oil phase are shown in Table 1, and the measurement results of the viscosity are shown in FIG.

[Table 1] ──────────────────────────────────── Properties of isostearyl polyglycolide Oil phase separation average Degree of polymerization ──────────────────────────────────── 1.9 White turbid gel-like 2.0 White turbid gel Yes 2.1 Clear, slightly viscous solution None 2.15 No clear liquid 2.2 No clear liquid 2.3 No clear liquid ─────────────────── ──────────────────

As can be seen from Table 1, the average degree of polymerization is 2.1.
When the amount is less than the above, the thickening gelling ability of isostearyl polyglucoside is exerted, the system becomes a gel state, and the oil phase cannot be separated to solubilize the oil component. On the other hand, when the average degree of polymerization of isostearyl polyglucoside is 2.1 or more, the solubilizing ability is exerted, the oil is solubilized and a uniform and transparent one liquid phase is exhibited, and the solution is low. The viscosity was liquid and no increase in viscosity was observed.

FIG. 1 shows the change in viscosity of isostearyl polyglucoside depending on the average degree of polymerization. When the average degree of polymerization is less than 2.1, the thickening and gelling ability is exhibited and the viscosity of the system is increased. However, it can be seen that when the average degree of polymerization is 2.1 or more, the thickening and gelling ability is not exhibited at all. From the above, it is understood that in the solubilizer of the present invention, the average degree of polymerization of the branched aliphatic polyglycoside needs to be 2.1 or more.

[0025]

[Examples] Production examples of branched aliphatic polyglycoside as a solubilizing agent according to the present invention and blending examples of cosmetics containing the same are given below, but the present invention is not limited thereto. Production Example 3 40.5 g (225 mmol) of glucose and 0.19 g (1 mmol) of paratoluenesulfonic acid were added to 7.97 g (378 mmol) of isomyristyl polyglucoside isomyristyl alcohol, and the mixture was stirred under nitrogen for 16 hours under reduced pressure for 16 hours. Reacted The reaction product was cooled to room temperature, and purified water, ethyl acetate, and methanol were added to the reaction system for partition. The aqueous layer was concentrated, and the obtained syrup was washed with acetone to obtain isomyristyl polyglucoside. When the average degree of polymerization of glucose in the obtained isomyristyl polyglucoside was examined in the same manner as in Production Example 1,
The average degree of polymerization was 2.6.

Formulation 1 Lotion (1) Ethanol 20.0 wt% (2) Hyaluronic acid 5.0 (3) Carboxyvinyl polymer 0.3 (4) Ethylparaben 0.1 (5) Isostearyl polyglucoside 5. 0 (Average degree of polymerization 2.5) (6) Purified water Residual (7) Perfume Suitable

(1) to (6) were well mixed and dissolved to obtain a lotion. This lotion had a transparent appearance and had a moist and good feeling of use. Also, 0 ℃, 25 ℃, 50
When stored at ℃, all of them were stable and no separation occurred. In addition, as a comparative example, instead of isostearyl polyglucoside, a nonionic surfactant POE (1
5) When a lotion was similarly prepared using 5.0 wt% of oleyl ether, oil droplets were separated and the solubilizing ability for the oily component was low. From this, it was suggested that the solubilizing agent of the present invention has a higher solubilizing ability than conventional nonionic surfactants.

Formulation Example 2 Water phase part of lotion ; (1) Lactose 1.0 wt% (2) Carboxyvinyl polymer 1.0 (3) Isostearyl polyglucoside (average degree of polymerization 2.5) 6.0 (4) 1,3-Butylene glycol 4.0 (5) Purified water Residual alcohol part; (1) Ethanol 2.0 (2) Purified lecithin 0.2 (3) POE (60) Hydrogenated castor oil 0.1 (4) Fragrance 2.0 (5) Methylparaben 0.3

The oil phase part and the alcohol part were uniformly dissolved, and the alcohol part was added to the water phase part to solubilize it to obtain a lotion. This lotion had a transparent appearance and had a moist and good feeling of use. Also, 0 ℃, 25 ℃, 50 ℃
When it was stored in, all of them were stable and no separation occurred.

Formulation Example 3 Aqueous essence A part; (1) 1,3-butylene glycol 2.0 wt% (2) D-galactosamine 1.0 (3) arginine 0.5 (4) collagen 2.0 (5) Carboxymethyl Polymer 1.5 (6) Isostearyl Polyglucoside (Average Degree of Polymerization 2.6) 5.0 (7) Dipropylene Glycol Suitable Part B; (1) Ethanol Suitable (2) POE (60) Cured Castor Oil 2.0 (3) Vitamin E acetate 5.0 (4) Fragrance 7.0 (5) Oleyl alcohol Suitable (6) Methylparaben Residual C part; (1) Potassium hydroxide 0.1

Dissolve parts A and B uniformly,
Part B was added to part to mix and solubilize, and part C was further added to obtain an essence. This essence has a transparent appearance,
It was a moist and good feeling. Also, 0 ℃, 25
When stored at 0 ° C and 50 ° C, both were stable and no separation or the like occurred.

[0032]

As described above, the solubilizer of the present invention is characterized by containing a branched aliphatic polyglycoside and having an average degree of polymerization of the branched aliphatic polyglycoside of 2.1 or more. However, this has the effect of exhibiting excellent safety, stability and solubilizing ability, and having a good feeling of use when applied to the skin.

[Brief description of drawings]

FIG. 1 is a diagram showing a change in viscosity according to an average degree of polymerization of an isostearyl polyglucoside solution which is an example of the present invention.

Claims (2)

[Claims] 1. A solubilizer comprising a branched aliphatic polyglycoside represented by the following general formula 1 and having an average degree of polymerization of the branched aliphatic polyglycoside of 2.1 or more. . ## STR00001 ## Gn-O-R (In the formula, Gn means a residue obtained by removing a glycosidic hydroxyl group from a monosaccharide G dehydrated and condensed at a degree of polymerization of n.
n is an integer of 1 or more. Further, R means a branched fatty chain having a glycoside bond with Gn and having a total carbon number of 8 to 32. ) 2. A cosmetic containing the solubilizer according to claim 1.