JP2016172700A - Emulsified composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an oil-in-water emulsion composition having excellent moisture retention action.SOLUTION: An oil-in-water emulsion composition contains alkyl glycoside represented by general formula (1) (where G is a sugar residue, Rs independently represent a hydrogen atom or a C1-C3 alkyl group, and n is an integer of 1-4).SELECTED DRAWING: None

Description

  The present invention relates to an oil-in-water emulsion composition suitable for a skin external preparation.

  It is said that the decrease in the moisture retention ability in the skin impairs the barrier function of the skin, and at the same time changes the form of the skin and causes wrinkles and the like. Therefore, conventionally, in the field of skin external preparations such as cosmetics, various techniques have been developed to increase the amount of water retained in the stratum corneum and improve the skin barrier function in the skin having a reduced moisturizing ability.

As components to be contained in a skin external preparation that exhibits a moisturizing action, polyhydric alcohols such as glycerin and polyglycerin, oily components such as oils and fatty acid esters, polymers such as hyaluronic acid, and the like are known.
Moreover, as a dosage form of skin external preparations, such as a milky lotion and a cream used for a moisturizing use, there exists an emulsifier type, and especially an oil-in-water type emulsion composition is preferable since a refreshing feeling is obtained. The emulsified composition is usually formed using a surfactant.

  By the way, in recent years, various sugar-based surfactants have been proposed as recyclable and environmentally-friendly surfactants, instead of conventional synthetic surfactants derived from petroleum raw materials, due to concerns about biological safety and environmental impact. For example, the isoprenoid chain type polyglycoside disclosed in Patent Document 1 has been proposed as a sugar-based surfactant that has a craft temperature lower than room temperature and can widely control the balance between hydrophilicity and hydrophobicity (Patent Document 1). .

Japanese Patent No. 3882067

When applying an oil-in-water emulsion composition to an external preparation for skin, it is desired to further improve the moisturizing action.
In view of such a situation, it is an object to provide an oil-in-water emulsion composition having an excellent moisturizing action.

  As a result of intensive studies to solve the above problems, the present inventors have found that an oil-in-water emulsion composition containing an alkyl glycoside having a specific structure has an excellent moisturizing action, and the present invention. It came to complete.

That is, the present invention is as follows.
[1] An oil-in-water emulsion composition containing an alkyl glycoside represented by the following general formula (1).

（式中、Ｇは糖残基を表し、Ｒは独立して水素原子又は炭素数１〜３のアルキル基を表し、ｎは１〜４の整数を表す。）

(In the formula, G represents a sugar residue, R independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and n represents an integer of 1 to 4).

[2] The alkyl glycoside is a sugar residue G in the general formula (1) is glucose, galactose, xylose, mannose, lyxose, arabinose, fructose, maltose, xylobiose, isomaltose, cellobiose, lactose, gentiobiose, malto Selected from triose, isomaltotriose, cellotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose, isomalttetraose, isomaltopentaose, isomalthexaose, and isomaltheptose The oil-in-water emulsion composition according to [1], which is a compound.
[3] The oil-in-water emulsion composition according to [1] or [2], wherein the alkyl glycoside is a compound represented by the following general formula (2).

（式中、Ｎは１〜７の整数を表し、Ｒは独立して水素原子又は炭素数１〜３のアルキル基を表し、ｎは１〜４の整数を表す。）

(In formula, N represents the integer of 1-7, R represents a hydrogen atom or a C1-C3 alkyl group independently, and n represents the integer of 1-4.)

[4] The oil-in-water emulsion composition according to any one of [1] to [3], wherein the content of the alkyl glycoside is 0.1 to 10% by mass with respect to the entire composition.
[5] The oil-in-water emulsion composition according to any one of [1] to [4], which is an external preparation for skin.
[6] The oil-in-water emulsion composition according to [5], which is a cosmetic.

The present invention provides an oil-in-water emulsion composition having an excellent moisturizing action. The oil-in-water emulsion composition of the present invention can be suitably used for a skin external preparation such as cosmetics.
In recent years, as a surfactant to be included in an external preparation for skin, a so-called natural system tends to be preferred in consideration of safety and environmental load, and a coupling reaction between a sugar and an aliphatic alcohol. The oil-in-water emulsified composition of the present invention using the alkyl glycoside obtained by the method satisfies the demand.

  The oil-in-water emulsion composition of the present invention contains an alkyl glycoside represented by the following general formula (1).

  In General Formula (1), G represents a sugar residue, R independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and n represents an integer of 1 to 4. That is, the alkyl glycoside represented by the general formula (1) has a structure in which a sugar residue G and an aliphatic alcohol are condensed.

The sugar residue G is a hydrophilic part in the alkyl glycoside according to the present invention, and is a residue of a monosaccharide or a polysaccharide.
Preferred monosaccharides include glucose, galactose, xylose, mannose, lyxose, arabinose, and fructose. The polysaccharide is preferably a disaccharide to a heptasaccharide, and maltose, xylobiose, isomaltose, cellobiose, lactose, gentiobiose, maltotriose, isomaltotriose, cellotriose, maltotetraose, maltopentaose, maltohexaose, Examples include maltoheptaose, isomalttetraose, isomaltpentaose, isomalthexaose, and isomaltheptose. Among these sugars, glucose is more preferably lactose, maltose, and maltotriose, and more preferably maltose and maltotriose.
In the general formula (1), the sugar residue G is preferably bonded (condensed) with an aliphatic alcohol at the hydroxyl group at the 1-position of the terminal sugar.

In the general formula (1), the fatty chain is a hydrophobic part in the alkyl glycoside according to the present invention.
The fatty chain portion may or may not have a branched chain, but preferably has a branched chain. That is, in the general formula (1), R independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, preferably an alkyl group having 1 to 3 carbon atoms, and more preferably a methyl group.

  As the alkyl glycoside according to the present invention, a compound represented by the following general formula (2) is more preferable.

（式中、Ｎは１〜７の整数を表し、Ｒは独立して水素原子又は炭素数１〜３のアルキル基を表し、ｎは１〜４の整数を表し、より好ましくはｎは２又は３である。）

(In the formula, N represents an integer of 1 to 7, R independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, n represents an integer of 1 to 4, more preferably n is 2 or 3)

  The alkylglycoside according to the present invention is more preferably a compound represented by the following general formula (3).

（式中、Ｎは１〜７の整数を表し、ｎは１〜４の整数を表し、より好ましくはｎは２又は３である。）

(In the formula, N represents an integer of 1 to 7, n represents an integer of 1 to 4, and more preferably n is 2 or 3.)

  The alkyl glycosides according to the present invention can be used in various ways, for example, glycosylation using bromide sugar, glycosylation using fluorinated sugar, glycosylation using trichloroacetimidate, glycosylation using acetylated sugar, etc. More specifically, it can be obtained by a known method, and more specifically, a synthesis step described in Japanese Patent No. 3882067, Japanese Patent No. 4817435, Japanese Patent No. 5207420, Japanese Patent Application Laid-Open No. 2013-129660, Japanese Patent Application Laid-Open No. 2012-17318, and the like. It is done.

  As content of the said alkyl glycoside in the composition of this invention, Preferably it is 0.1-10 mass% with respect to the whole composition, More preferably, it is 0.1-5 mass%, More preferably, it is 0.5-5. % By mass. By containing in such a range, the moisturizing effect becomes higher, and the feeling of use becomes better without stickiness.

In the oil-in-water emulsion composition of the present invention, the ratio of the water phase to the oil phase, that is, the internal phase ratio is not particularly limited. For example, the water phase: oil phase (mass ratio) is preferably 99: 1 to 4: 6, More preferably, it can be 97: 3 to 6: 4, and further preferably 19: 1 to 3: 1.
In addition, an oil phase is normally comprised with an oil-based component, and an oil-based component is not restricted to what is called an oil agent, but it suspends in 25-65 degreeC water by 1: 1 (mass ratio), and is left still for one day, Then, it separates from water Refers to ingredients (excluding surfactants).
Examples of oily components that can be blended in the oil-in-water emulsion composition of the present invention include polar oils, natural oils, hydrocarbon oils, non-polar silicone oils, polar silicone oils and the like; ultraviolet absorbers, ultraviolet scattering And UV protection agents such as agents.

Moreover, the composition of this invention can contain another arbitrary component, unless the effect is impaired.
The optional component is not particularly limited as long as it is a component that can be usually blended into a skin external preparation, and surfactants (cationic surfactants, anionic surfactants, nonionic surfactants, silicone surfactants) Etc.), various active ingredients, humectants, pH adjusters, thickeners, preservatives, powders, organically modified clay minerals and the like.
Examples of the active ingredient include a moisturizing ingredient, a whitening ingredient, a wrinkle improving ingredient, an anti-inflammatory ingredient, an extract derived from animals and plants, and the like, and only one kind may be contained, or two or more kinds may be contained.

  The oil-in-water emulsion composition of the present invention can be produced according to a conventional method.

The oil-in-water emulsion composition of the present invention has an excellent moisturizing action. Specifically, for example, when applied to the skin, the moisture retention amount in the stratum corneum can be increased, and the barrier function of the skin can be improved.
Therefore, the composition of the present invention can be preferably used as a skin external preparation. In particular, cosmetics (including quasi drugs) are preferable.

  EXAMPLES Hereinafter, although an Example demonstrates this invention still in detail, this invention is not limited to a following example, unless the summary is exceeded.

<Production example>
An oil-in-water emulsion composition was prepared according to the formulation shown in Table 1. That is, for Examples 1 to 11 and Comparative Examples 1 to 3, the components (a) to (d) were mixed after being uniformly dissolved at 50 to 60 ° C. in a stainless steel container, and stirred for 5 minutes with a homomixer. Samples were prepared. For Comparative Example 4, the components (A) to (C) were each uniformly dissolved at 50 to 60 ° C. in a stainless steel container and then mixed, and stirred for 5 minutes with a homomixer to prepare a sample.

<Test Example 1> Evaluation of stratum corneum moisture amount After patching the forearm of a healthy adult subject with an aqueous solution of sodium dodecyl sulfate (SDS) at a concentration of 0.5% for 24 hours to cause rough skin, Examples 1 to 11 and each sample of Comparative Examples 1 to 4 were applied daily in an appropriate amount for 7 days. Seven days after the start of application of the sample, the increase in the amount of water in the stratum corneum at the site was measured using SKICON200-EX (manufactured by IBM Corporation). The average of the measured values of 20 people for each sample was calculated. In addition, the test sample applied to each site was randomly assigned. The results are shown in Table 2.

<Test Example 2> TEWL Evaluation For a site treated in the same manner as in Test Example 1, the transdermal moisture transpiration (TEWL) value at the site 7 days after the start of application of the sample was measured using TEmeter TM210 (C + K). The recovery rate was determined using the following formula. The average value of the measured values of 20 people was calculated for each sample. The results are shown in Table 2.

なお、式中の記号は以下の意味を表す。
ＴＥＷＬ₁₀₀：肌あれ惹起前のＴＥＷＬ測定値
ＴＥＷＬ₀：パッチ直後のＴＥＷＬ測定値
ＴＥＷＬ_T：資料塗布後Ｔ日後のＴＥＷＬ測定値

In addition, the symbol in a formula represents the following meanings.
TEWL ₁₀₀ : TEWL measurement value before skin irritation TEWL ₀ : TEWL measurement value immediately after patch TEWL _T : TEWL measurement value T days after material application

<Test Example 3> Appearance Evaluation The site where each sample was applied in Test Examples 1 and 2 was observed using an enlarged video 7 days after the start of sample application, and the state of the stratum corneum was evaluated in the following five stages. The results are shown in Table 2.
Stratum corneum desquamation
5: Not observed at all.
4: Almost not observed.
3: Observed slightly.
2: Slightly observed.
1: Observed considerably.

  The present invention provides an oil-in-water emulsion composition having an excellent moisturizing action. Since such a composition can be suitably used for an external preparation for skin and the like and can exhibit an excellent moisturizing effect, it is very useful industrially.

Claims (6)

An oil-in-water emulsion composition comprising an alkyl glycoside represented by the following general formula (1).

(In the formula, G represents a sugar residue, R independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and n represents an integer of 1 to 4).   The alkyl glycoside is a sugar residue G in the general formula (1) is glucose, galactose, xylose, mannose, lyxose, arabinose, fructose, maltose, xylobiose, isomaltose, cellobiose, lactose, gentiobiose, maltotriose, Is a compound selected from isomaltotriose, cellotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose, isomalttetraose, isomaltopentaose, isomalthexaose, and isomaltheptose The oil-in-water emulsion composition according to claim 1. The oil-in-water emulsion composition according to claim 1 or 2, wherein the alkyl glycoside is a compound represented by the following general formula (2).

(In formula, N represents the integer of 1-7, R represents a hydrogen atom or a C1-C3 alkyl group independently, and n represents the integer of 1-4.)   The oil-in-water emulsion composition according to any one of claims 1 to 3, wherein the content of the alkyl glycoside is 0.1 to 10% by mass relative to the entire composition.   The oil-in-water emulsion composition according to any one of claims 1 to 4, which is a skin external preparation.   The oil-in-water emulsion composition according to claim 5, which is a cosmetic.