JPH11147816A - Humidifier raw material and humectant comprising the same - Google Patents

Abstract

(57) [Summary] A humectant raw material is an ester of a disaccharide or a trisaccharide and docosahexaenoic acid or γ-linolenic acid, and the composition of the ester is 10% or less of a monoester component,
It is composed of a composition ratio of 5 to 50% of a diester component and 40 to 95% of a polyester component of tri or higher. The above-mentioned humectant raw material is added to the humectant for skin or hair (0.1 to 20%). EFFECT OF THE INVENTION The moisturizing agent of the present invention can maintain a suitable amount of moisture in the stratum corneum without stickiness or drying, and the good moisturizing state can be maintained for a long time. Can be.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to all fields in which an ester of a disaccharide or trisaccharide and docosahexaenoic acid (hereinafter abbreviated as DHA) or γ-linolenic acid is used as a humectant.

[0002]

2. Description of the Related Art In recent years, various studies have been made on DHA, which is a kind of n-3 polyunsaturated fatty acid, and knowledge that it has various physiological activities is increasing day by day. ing. DHA derivatives are now being used in various industries such as food, cosmetics, and pharmaceuticals. Further, γ-linolenic acid is derived from evening primrose oil, borage oil, Mortierella oil and the like, and is being used for the treatment of atopic dermatitis as its use.

In fact, according to the prior art, many esters of DHA with compounds having a hydroxyl group such as monosaccharides and glycerin have been developed. Examples of the use of the physiological activity derived from DHA include those esters as anti-inflammatory agents and whitening agents.

[0004] For example, Japanese Patent Application Laid-Open No. 6-293789 entitled "Glycosides of polyunsaturated fatty acids and a method for producing the same" describes DHA.
Japanese Patent Application Laid-Open No. 7-109128, "External preparations for treating allergic skin diseases" discloses ethyl esters, monoglycerides, diglycerides, triglycerides, etc., but these are actually used as moisturizer components. There is no statement to use.

In general, the following properties are required as properties requiring a humectant. An oil film can be formed to suppress water evaporation. There must be a hydrophilic part in the molecule. However, the above-mentioned esters have a structure in which the number of polar groups present in a molecule is small or no, although an oil film can be formed, so that a large number of water molecules are coordinated per molecule of the ester. I can't let that happen. As a result, even if an attempt was made to use these esters as a humectant, a sufficient effect as a humectant could not be obtained.

[0006]

SUMMARY OF THE INVENTION In order to solve the above-mentioned problems, the inventors of the present invention have found that, in the course of research, the ester of a disaccharide or a trisaccharide and DHA is rich in polar groups in molecular structure. While having an oil film formation is also possible, and similar knowledge was obtained for γ-linolenic acid,
By utilizing this property, an excellent humectant is intended to be obtained using a humectant raw material.

[0007]

The invention according to claim 1 of the present invention uses an ester of a disaccharide or a trisaccharide with DHA or γ-linolenic acid and uses a monoester component of 10% or less and a diester component of 5 to 5%. The present invention relates to a humectant raw material having a composition ratio of 50% and 40 to 95% of a polyester component of a bird or more. The invention according to claim 2 is that the sugar constituting the ester with DHA or γ-linolenic acid is selected from sucrose, trehalose, maltitol and lactitol.
The humectant raw material according to claim 1, wherein the humectant raw material is prepared with one or more kinds.

A third aspect of the present invention relates to a skin or hair moisturizer containing the moisturizing raw material according to the first or second aspect. According to a fourth aspect of the present invention, the humectant raw material according to the first or second aspect is used in an amount of 0.1 to 2%.
It relates to a humectant for skin or hair containing 0%.

Hereinafter, the configuration of the present invention will be described in detail.

The disaccharide or trisaccharide used in the present invention and DH
As described above, regarding the ester with A or γ-linolenic acid, during the course of research, the inventors of the present invention found that the ester of disaccharide or trisaccharide with DHA or γ-linolenic acid was
It was found that an oil film could be formed while having abundant polar groups in the molecular structure, and this property was utilized. Although monosaccharides can form an oil film, they are unsuitable as moisturizer raw materials because the water molecules coordinated per molecule are small and the water content of the skin cannot be kept well. On the other hand, in the case of tetrasaccharides or more, although the number of water molecules coordinated per molecule is large, the formation of an oil film becomes difficult due to the enlargement of the hydrophilic portion due to the longer sugar chain, which is also unsuitable. .

The sugars used to prepare the esters are, for example, maltose, lactose, cellobiose, gentibiose, sucrose, trehalose, lactitol, maltitol, etc. from disaccharides and raffinose from trisaccharides.
Melezitose, etc., but in the present invention, 2
The sucrose, trehalose, lactitol and maltitol, which are saccharides, were found to be particularly preferred during the course of the study of the present invention.

The ester prepared in the present invention may be prepared according to a conventional method, and dimethyl sulfoxide (D
MSO), dimethylformamide (DMF) or N
It may be produced by a transesterification reaction using -methyl-2-pyrrolidone as a solvent, a microemulsion ester method, a solventless ester method, or the like.

When preparing a humectant raw material using the above-mentioned sugar DHA ester or sugar γ-linolenic acid ester,
First, these esters have the following composition ratios (a) to (c). (A) Monoester component: 10% or less (b) Diester component: 5 to 50% (c) Tri or higher polyester component: 40 to 95% This is the skin of sugar DHA ester or sugar γ-linolenic acid ester mixture. This is a result of examining the balance between the ability to form an oil film in the stratum corneum and the ability to coordinate water molecules, that is, the monoester component is kept low to 10% or less, and the diester component is comparable to the polyester component of the tri- or higher component. Alternatively, it is from a research result that a good balance between the ability to form an oil film and the ability to coordinate water molecules can be obtained by adding a smaller amount.

Next, the humectant raw material having the composition of (a) to (c) is mixed with the humectant, and it is particularly preferable to set the mixing ratio to 0.1 to 20%. The basis is that, when formulating the humectant of the present invention in cosmetics, pharmaceuticals, etc., it is possible to add other additives or solvents according to the purpose, and to obtain an excellent feeling of use and solubility, thereby obtaining a humectant. This is to make it substantially usable.

Examples, comparative examples, and test examples will be described below to clarify the effects of the present invention.

[Synthesis of Ester] First, an ester used in the present invention was synthesized according to the prescription shown in Table 1 by the following steps. The prescribed amounts of sugar and DMSO are dissolved by heating in a flask. Next, the prescribed amount of methyl docosahexaenoate or γ
-Adding methyl linolenate to the above solution,
A prescribed amount of potassium carbonate is added as a catalyst. The above-mentioned solution was subjected to a vacuum of 15 to 20 mmHg,
The transesterification is carried out at a temperature of 92 to 95 ° C for 6 hours. After the reaction, the catalyst is removed by neutralization → filtration, followed by distillation under reduced pressure to remove almost all of the DMSO. The reaction was performed by adding three times the amount of methyl ethyl ketone (MEK).
And then recrystallized, filtered and dried to obtain the ester of the present invention. The composition of each ester in Examples 1 to 3 was examined. The method was described as follows: Daiichi Kogyo Seiyaku (published on July 10, 1984): “Sugar Ester Monogatari”, pp. 60-
The measurement was carried out based on the method for measuring the monoester content described on page 61. The outline is as follows. Monoester, diester, and tri- or higher polyester in the sugar ester are separated by TLC (thin layer chromatography), and the bound sugar is measured by colorimetry. ) Was calculated. Table 2 shows the results.

[0016]

Examples 1 to 3 Next, in the sugar DHA ester shown in Table 2,
Example 1 containing moisturizer raw material containing a large amount of polyester
To 3.

[0017]

Example 4 Among the sugar γ-linolenates shown in Table 2, the one containing a large amount of polyester was designated as Example 4 of the humectant raw material.

[0018]

Comparative Example 1 The sugar DHA ester shown in Table 2 containing a large amount of a monoester component was used as Comparative Example 1 of a humectant raw material.

[0019]

Comparative Example 2 Comparative Example 2 was an ester of a dextrin hydrolyzate having an average chain length of 4 in Table 2 and DHA.

[0020]

Comparative Example 3 As a comparative example 3 using a DHA ester of the prior art, a monoglyceride of DHA was used.

[0021]

Comparative Example 4 The sugar γ-linolenic ester shown in Table 2 containing a large amount of a monoester component was used as Comparative Example 4 of the humectant raw material.

[0022]

[Test 1] As described above, in order to demonstrate that the humectant is suitable as a humectant raw material of the present invention, Examples 1 to 4 were used.
And Comparative Examples 1 to 4, the moisture retention properties of each substance were examined. And it carried out by the following procedures as a technique of examining moisture retention. 100 g of each sample was stored in a desiccator for one day to remove water. Each dried sample was stored for 1 hour in a storage room at a relative humidity of 80% and a temperature of 20 ° C., and the weight of each sample was measured every 10 minutes immediately after storage. Next, each sample was transferred to a storage room having a relative humidity of 20% and a temperature of 20 ° C., and stored for 1 hour.
Each sample was weighed every minute. FIG. 1 shows the change over time of the moisture absorbed by each sample from the change in weight of each sample between this step and the process.

As is clear from FIG. 1, the humectant raw materials of Examples 1 to 4 of the present invention absorb less moisture than Comparative Example 2, and Comparative Examples 1, 3 and 3 It was found to have the ability to absorb more moisture than Example 4. This means that Examples 1-4 are moisturizers,
It was considered that it was not sticky or dry, that is, suitable for giving the skin an appropriate amount of moisture. Then, the inventor of the present invention prepared a humectant using Examples 1 to 4 and Comparative Examples 1 to 4, and conducted a test of actually applying the humectant to the skin.

[0024]

Examples 5 to 12 Based on the formulations shown in Table 3, the ingredients were mixed to prepare Examples 4 to 12 of humectants.

[0025]

Comparative Examples 5 to 8 Based on the formulations shown in Table 3, each component was mixed to prepare Comparative Examples 5 to 8 of humectants.

[0026]

[Test 2] Using Examples 5 to 12 and Comparative Examples 5 to 8,
Actually, 0.05 g was applied to the skin of the forearm of 10 subjects, and immediately after the application, the moisturizing condition of the skin after 5 minutes, 10 minutes, 15 minutes, 30 minutes, and 60 minutes was measured by the subject himself. Sensory evaluation was performed. The evaluation method is that each subject compares the applied part of each sample with the uncoated blank part and evaluates it in three stages of moderate moisture retention, stickiness and dryness,
Table 1 shows the total score for 10 test subjects, with 1 point when there is appropriate moisturizing property and 0 point when both sticky and dry.

[0025]

[Test 3] Using Examples 5 to 12 and Comparative Examples 5 to 8,
Actually, 0.05 g was applied to the skin of the forearm of 10 subjects, and after 3 hours, 6 hours, 12 hours, 24 hours,
The subject himself / herself evaluated the moisturizing state of the skin 48 hours later. As for the evaluation method, each subject compares the applied part of each sample with the uncoated blank part and evaluates it in three stages of moderate moisturizing property, stickiness and dryness, and has an appropriate moisturizing property. In Table 5, the total score for 10 subjects is described as 1 point, and the case of stickiness and the case of dryness are both 0 points.

The results of Test 2 show that the humectant of the present invention has an effect of forming an oil film in the stratum corneum of the skin to suppress the evaporation of water and the sugar of the ester constituting the humectant as compared with Comparative Examples 5 to 8. Since the portion was excellent in balance with the effect of coordinating water molecules, it was proved that the skin had a suitable amount of water in the stratum corneum, and was not sticky or dry. In addition, the result of Test 3 shows that the good moisturizing state is maintained for a long time.

[0027]

EFFECT OF THE INVENTION The moisturizing agent of the present invention can maintain a suitable amount of moisture in the stratum corneum without stickiness or drying, and the good moisturizing state can be maintained for a long time. Can be. Therefore, by prescribing this humectant in cosmetics and the like, it becomes possible to provide an excellent cosmetic which can provide a suitable amount of moisture to the skin for a long period of time, and as a result, to improve the marketability of the cosmetics Becomes possible.

Claims (4)

[Claims] 1. An ester of a disaccharide or trisaccharide with docosahexaenoic acid or γ-linolenic acid, wherein the composition of the ester is 10% or less of a monoester component and 5 to 5% of a diester component.
A humectant raw material comprising a composition ratio of 50% and a composition of 40 to 95% of a polyester component of a bird or more. 2. The method according to claim 1, wherein the sugar is an ester of one or more selected from sucrose, trehalose, lactitol and maltitol with docosahexaenoic acid or γ-linolenic acid. Moisturizer raw material. 3. A humectant for skin or hair, wherein the humectant raw material according to claim 1 or 2 is blended. 4. The mixing ratio of the humectant raw material is 0.1 to 2
The humectant for skin or hair according to claim 3, wherein the humectant is 0%.