JP6787253B2 - Cosmetics for skin care - Google Patents

Description

The present invention relates to skin care cosmetics containing a phosphorylcholine derivative.

Moisturizing is one of the effects of skin care cosmetics. Therefore, polyhydric alcohols and oils are added to skin care cosmetics such as lotions for the purpose of moisturizing, but when used in large amounts, they cause stickiness. Therefore, various studies have been conducted so far to moisturize while reducing stickiness. Patent Document 1 describes a skin cosmetic that contains a specific alkylene oxide derivative and a polymer compound to maintain a moisturizing effect but is not sticky. Further, Patent Document 2 describes a cosmetic containing a polymer having a phosphorylcholine group, which is not sticky, has a good feel, and has an excellent moisturizing effect. Further, Patent Document 3 describes that a specific phosphorylcholine derivative has an excellent moisturizing effect on the skin and does not impair the feeling of use when contained in cosmetics.

On the other hand, one of the worries of women who put on makeup on their face is the powderiness after applying powder foundation. Powder foundations are characterized by their ease of use and refreshing feel, but on the other hand, they often absorb moisture from the skin after application, resulting in a powdery and dry finish. In recent years, with the advancement of women into society, so-called "short-time beauty" has attracted attention, and there is a tendency to prefer simplification of skin care steps. However, if skin care is completed with only lotion during dry seasons such as winter, then There was a problem that the finish of the powder foundation became more powdery.
Therefore, there has been a demand from the market for water-based cosmetics that have a moisturizing sensation but are not sticky, and also have the effect of preventing powderiness after applying a powder foundation.

Japanese Patent No. 4670366 Japanese Patent No. 4524846 Japanese Unexamined Patent Publication No. 2011-213602

The present invention provides a skin care cosmetic that has a moisturizing feeling, is not sticky, and has an effect of preventing powderiness after applying a powder foundation.

（式（Ｉ）において、Ｒ^１及びＲ^２は同一または異なる基であって、炭素数１４〜２２のアルキル基を表す。）
（Ｂ）下記の式（ＩＩ）で示されるサーファクチンもしくはその塩：０．０１〜０．７質量％

（式中、＊は光学活性点を表す。Ｘは、ロイシン、イソロイシン、及びバリンから選ばれるアミノ酸構造を表し、Ｒは、炭素数９〜１３のアルキル基を表す。Ｍは、水素原子、アルカリ金属原子、アルカリ土類金属原子、又は置換されていてもよいアンモニウムを表す。）
（Ｃ）炭素数３〜６の２〜４価の多価アルコール：０．１〜１５質量％ As a result of diligent studies by the present inventor, the above-mentioned problems have been solved by a skin care cosmetic containing a specific amount of each of the following three specific components.
That is, it is a skin care cosmetic containing the following components (A) to (C).
(A) Compound represented by the following formula (I): 0.01 to 0.7% by mass

(In formula (I), R ¹ and R ² are the same or different groups and represent alkyl groups having 14 to 22 carbon atoms.)
(B) Surfactin represented by the following formula (II) or a salt thereof: 0.01 to 0.7% by mass

(In the formula, * represents an optically active point. X represents an amino acid structure selected from leucine, isoleucine, and valine, R represents an alkyl group having 9 to 13 carbon atoms, and M represents a hydrogen atom and an alkali. Represents a metal atom, an alkaline earth metal atom, or an optionally substituted ammonium.)
(C) 2-Tetravalent polyhydric alcohol having 3 to 6 carbon atoms: 0.1 to 15% by mass

When the skin care cosmetic of the present invention is applied to the skin, it does not become sticky while feeling a moisturizing feeling, and even if a powder foundation is applied from above, it does not become powdery.

Hereinafter, the present invention will be described in detail. In addition, in the description of "(A) compound represented by the following formula (I): 0.01 to 0.7% by mass", the description before ":" is "skin care cosmetics". The description after the ":" indicates the content of the compound in the "skin care cosmetics".

In the formula (I) of the component (A) used in the cosmetic of the present invention, R ¹ and R ² are the same or different groups, and the alkyl group having 14 to 22 carbon atoms has 14 to 22 carbon atoms. Representing a linear or branched alkyl group, specifically, tetradecyl group, hexadecyl group, octadecyl group, eikosacil group, docosyl group, isotetradecyl group, isohexadecyl group, isooctadecyl group, isoeicosacyl group, isodocosyl Examples thereof include a group, a 2-butyl decyl group, a 2-hexyl decyl group, a 2-octyl decyl group, a 2-decanyl decyl group and a 2-dodecanyl decyl group. Among these, tetradecyl group, hexadecyl group, octadecyl group, eikosacil group, and docosyl group, which are linear alkyl groups, are more preferable in that they exhibit higher moisturizing properties. When the number of carbon atoms of the alkyl group is less than 14, the moisturizing feeling and the safety are lowered. On the other hand, if the number of carbon atoms of the alkyl group exceeds 22, in addition to the difficulty in obtaining the raw material, the mixability of the obtained PC compound in the cosmetic may be impaired.

The component (B) is a surfactin represented by the formula (II) or a salt thereof. In the formula (II), "L-Leu" represents an L-leucine structure, "D-Leu" represents a D-leucine structure, and "L-Val" represents an L-valine structure. X represents the amino acid structure of any one selected from L-leucine, L-isoleucine, and L-valine. X preferably has an L-leucine structure.

R represents an alkyl group having 9 to 13 carbon atoms, that is, a linear or branched alkyl group having 9 to 13 carbon atoms, and examples of the linear alkyl group having 9 to 13 carbon atoms include a nonyl group and a decyl group. Examples thereof include an undecyl group, a dodecyl group, and a tridecyl group. Examples of the branched alkyl group having 9 to 13 carbon atoms include a 7-methyloctyl group, an 8-methylnonyl group, a 9-methyldecyl group, a 10-methylundecyl group, an 11-methyldodecyl group and a 6-methyloctyl group. Examples thereof include a 7-methylnonyl group, an 8-methyldecyl group, a 9-methylundecyl group and a 10-methyldodecyl group. These may be substituted with one or more substituents. Examples of the substituent include an amino group, a hydroxyl group, a phenyl group, an aryl group, an alkanoyl group, an alkenyl group, an alkynyl group, an alkoxyl group, a nitro group, a halogen atom and the like. R is preferably a 10-methylundecyl group.

M represents a hydrogen atom, an alkali metal atom, an alkaline earth metal atom, ammonium which may be substituted, and the like. Here, the alkali metal atom is not particularly limited, but represents a lithium atom, a sodium atom, a potassium atom, or the like. The alkaline earth metal atom is not particularly limited, but represents a beryllium atom, a magnesium atom, a calcium atom and the like. Ammonium which may be substituted is not particularly limited as long as it forms a surfactin and salts, other ammonia, mono-substituted ammonium (RNH 4 ^_+), disubstituted ammonium represents a trisubstituted ammonium. Examples of the substituent of ammonium include alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group and tert-butyl group, and aralkyl groups such as benzyl group, methylbenzyl group and phenylethyl group. Examples thereof include organic groups such as an aryl group such as a group, a phenyl group, a toluyl group and a xsilyl group. Specific examples thereof include methylammonium, ethylammonium, benzylammonium, diethylammonium, dicyclohexylammonium, N-benzyl-N-ethylammonium, triethylammonium and the like. These organic groups may be further substituted with one or more substituents.
As M, an alkali metal atom (sodium atom, potassium atom, etc.) is preferable, and a sodium atom is more preferable.

The component (C) is a 2- to 4-valent polyhydric alcohol having 3 to 6 carbon atoms, and is, for example, glycerin, pentylene glycol, 1,3-butylene glycol, erythritol, propylene glycol, dipropylene glycol, diglycerin, f. Examples thereof include polyhydric alcohols such as xylene glycol and isopylene glycol. Of these, glycerin, propylene glucol, and diglycerin are preferable, and glycerin is more preferable. When the carbon number of the component (C) is 2 or less, or the valence is 5 or more, stickiness is felt. In addition, when the number of carbon atoms is 7 or more or the valence is 2 or less, stickiness is felt.

Ingredient (D) is an oil that is liquid at 25 ° C., ester oils such as ethylhexyl palmitate, isopropyl myristate, cetyl sebacate, triglycerides such as olive oil and macadamia nut oil, hydrocarbon oils such as squalane and liquid paraffin, and oleic alcohol. Higher alcohols such as, higher fatty acids such as oleic acid, silicone oils such as dimethylpolysiloxane and cyclomethicone, lignans, vitamin E, oil-soluble vitamin C, vitamin A derivatives, ceramides, ceramide-like structural substances, oil-soluble ultraviolet absorbers. Functional oily substances such as. These can be used alone or in combination of two or more. Among them, triglyceride and ester oil are preferable, and ester oil is more preferable.

The blending amount of the components (A) to (D) is indicated by mass% when the total mass of the skin care cosmetics is 100% by mass.
The content of the component (A) in the skin care cosmetic of the present invention is 0.01 to 0.7% by mass, preferably 0.1 to 0.5% by mass, and more preferably 0.2. ~ 0.4% by mass. When the content of the component (A) is less than 0.01% by mass, the moisturizing feeling becomes insufficient, and a powdery feeling is felt after applying the foundation. Further, when the content of the component (A) is more than 0.7% by mass, stickiness is felt.

The content of the component (B) is 0.01 to 0.7% by mass, preferably 0.1 to 0.5% by mass, and more preferably 0.2 to 0.4% by mass. If the content of the component (B) is less than 0.01% by mass, a powdery feeling is felt after applying the powder foundation. When the content of the component (B) is more than 0.7% by mass, it gives stickiness and feels powdery after applying the foundation.

The content of the component (C) is 0.1 to 15% by mass, preferably 2 to 12% by mass, and more preferably 5 to 10% by mass. If the content of the component (C) is less than 0.1% by mass, the moisturizing feeling is insufficient. When the content of the component (C) is more than 15% by mass, it gives stickiness.

The content of the component (D) is 0.001 to 0.05% by mass, preferably 0.005 to 0.03% by mass, and more preferably 0.01 to 0.02% by mass. If the content of the component (D) is more than 0.05% by mass, stickiness is felt.

The skin care cosmetics of the present invention may contain additives commonly used in cosmetics and pharmaceuticals as long as the effects of the present invention are not impaired. In addition, the skin care cosmetic of the present invention is appropriately diluted with water before use.

Hereinafter, the present invention will be described in more detail based on Examples and Comparative Examples, but the present invention is not limited to the following Examples.
Table 1 shows the compounds corresponding to the component (A) used in the examples.

<Synthesis of Synthesis Examples 1 to 3>
(Synthesis Example 1)
To a 1 L round flask equipped with a thermometer, a dropping funnel and a stirrer, add 48.4 g (0.2 mol) of 1-hexadecanol, 20.2 g (0.2 mol) of triethylamine and 280 g of tetrahydrafuran, and at 4 ° C. Stirred and mixed. Then, a mixed solution of 28.5 g (0.2 mol) of 2-chloro-2-oxo-1,3,2-dioxaphosphoran and 60 g of tetrahydrafuran was added to the above-cooled mixed solution using a dropping funnel. Dropped. The dropping was carried out gradually over 2 hours while stirring the cooled mixed solvent and cooling so that the reaction temperature did not exceed 10 ° C. After completion of the dropping, stirring was continued for another 1 hour. Subsequently, the triethylamine hydrochloride precipitated as a by-product was separated into furnaces. The entire amount of the obtained filtrate was put into a 2 L round-bottom flask equipped with a stirrer, 118.8 g (0.4 mol) of N, N-dimethyloctadecylamine and 380 g of acetonitrile were added, and the mixture was stirred at 70 ° C. for 12 hours. Then, the precipitate obtained by cooling the reaction solution was separated by filtration and dried under reduced pressure at 70 ° C. to obtain 23.6 g of crude crystals (yield 18.3%).

(Synthesis example 2)
54.0 g (0.2 mol) of 1-octadecanol was used as the raw material alcohol instead of 1-hexadecanol, and N, N-methylbehenylamine was used as the raw material amine instead of N, N-dimethyloctadecylamine. The same operation as in Synthesis Example 1 was carried out except that 141.2 g (0.4 mol) was used, and 26.1 g (yield 17.9%) of white crystals (hereinafter abbreviated as GmPC2) was obtained.

(Synthesis Example 3)
65.2 g (0.2 mol) of 1-docosanol was used as the raw material alcohol instead of 1-hexadecanol, and N, N-dimethylhexadecylamine 107 was used as the raw material amine instead of N, N-dimethyloctadecylamine. The same operation as in Synthesis Example 1 was carried out except that 0.6 g (0.4 mol) was used, and 18.1 g (yield 12.9%) of white crystals (hereinafter abbreviated as GmPC3) was obtained.

The compounds used in the examples in Table 2 and the comparative examples in Table 3 are shown below.
Ingredient (B) Sodium surfactin (X: L-leucine structure, R: 10-methylundecyl group, M: sodium atom, product name: Kaneka surfactin, manufacturer: Kaneka Corporation)
Ingredient (B') PEG-60 hydrogenated castor oil (Product name: Uniox HC-60, Manufacturer: NOF Corporation)
Polysorbate 60 (Product name: Willsurf TF-60, Manufacturer: NOF CORPORATION)
Sodium cocoyl glutamate (Product name: Amisoft CS-11, Manufacturer: Ajinomoto Co., Inc.)
Ingredient (C) Glycerin (Product name: RG ・ Co ・ P, Manufacturer: NOF Corporation)
Diglycerin (Product name: Unigli G-2, Manufacturer: NOF CORPORATION)
Ingredient (C') Ethanol (Product name: Ethanol (99.5), Distributor: Wako Pure Chemical Industries, Ltd.)
Polyglycerin-4 (Product name: Polyglycerin # 310, Manufacturer: Sakamoto Yakuhin Kogyo Co., Ltd.)
Ingredient (D) Ethylhexyl palmitate (Product name: Unistar MB-816, Manufacturer: NOF CORPORATION)
Other ion-exchanged water

<Preparation of cosmetics>
Ingredients (A)-(D) were placed in a beaker according to the formulations shown in Tables 2 and 3 and stirred at 80 ° C. with a magnetic stirrer until uniform. This was diluted 10-fold with ion-exchanged water and used for the following evaluation.

<< Evaluation method >>
The skin care cosmetics of the examples in Table 2 and the comparative examples in Table 3 were evaluated. The evaluation items were "moisturizing feeling", "non-stickiness", and "powderiness after applying powder foundation".

<Moisturizing feeling>
After washing the face and lightly towel-drying the face, 1.0 g of the skin care cosmetics of Examples and Comparative Examples was applied, and the moisturizing feeling after 5 minutes was evaluated by a specialized panelist according to the following criteria.
⊚: Feeling moisturizing 〇: Feeling rather moisturizing △: Feeling rather moisturizing ×: Not feeling moisturizing In the evaluation, those evaluated as ○ or ◎ were accepted.

<Non-stickiness>
After washing the face and lightly towel-drying the face, 1.0 g of the skin care cosmetics of Examples and Comparative Examples was applied, and the non-stickiness after 5 minutes was evaluated by a specialized panelist according to the following criteria.
⊚: No stickiness 〇: Rather non-sticky △: Rather sticky ×: Sticky In the evaluation, those evaluated as ○ or ◎ were accepted.

<Powderiness after applying powder foundation>
In a constant temperature and humidity room set at a temperature of 10 ° C and a humidity of 35%, after washing the face, apply 1.0 g of the skin care cosmetics of Examples and Comparative Examples to the lightly towel-dried face, and after 3 minutes, apply powder foundation normally. I had it applied as it was. We asked a specialist panelist to evaluate the powderiness after applying the powder foundation according to the following criteria.
⊚: Not powdery 〇: Not powdery △: Rather powdery ×: Powdery In the evaluation, those evaluated as ○ or ◎ were accepted.

The results are shown in Tables 2 and 3.

As shown in Table 2, the skin care cosmetics of Examples 1 to 8 according to the present invention have a moisturizing feeling, are not sticky, and have an effect of preventing powderiness after applying a powder foundation. Became clear.
On the other hand, in Comparative Examples 1 to 12, sufficient effects were not obtained.
That is, in Comparative Example 1, since the component (A) was used in an amount of less than 0.01% by mass, the moisturizing feeling was insufficient, and at the same time, a powdery feeling was felt after applying the powder foundation.
In Comparative Example 2, since the component (A) was used in an amount of more than 0.7% by mass, stickiness was felt.
In Comparative Example 3, since the component (B) was used in an amount of less than 0.01% by mass, a powdery feeling was felt after applying the powder foundation.
In Comparative Example 4, since the component (B) was used in an amount of more than 0.7% by mass, a stickiness was felt and a powdery feeling was felt after the powder foundation was applied.
In Comparative Example 5, PEG-60 hydrogenated castor oil was used instead of the component (B), so that it felt sticky and powdery after applying the powder foundation.
In Comparative Example 6, since polysorbate 60 was used instead of the component (B), a powdery feeling was felt after applying the powder foundation.
In Comparative Example 7, since sodium cocoyl glutamate was used instead of the component (B), stickiness was felt and powderiness was felt after applying the powder foundation.
In Comparative Example 8, since the component (C) was used in an amount of less than 0.1% by mass, the moisturizing feeling was insufficient.
In Comparative Example 9, since the component (C) was used in an amount of more than 15% by mass, stickiness was felt.
In Comparative Example 10, since ethanol was used instead of the component (C), the moisturizing feeling was insufficient, and a powdery feeling was felt after applying the powder foundation.
In Comparative Example 11, since polyglycerin was used instead of the component (C), stickiness was felt and powderiness was felt after applying the powder foundation.
In Comparative Example 12, since the component (D) was used in an amount of more than 0.05% by mass, stickiness was felt.

Hereinafter, an example of prescribing a skin care cosmetic according to the present invention will be shown.
<Prescription example 1: Toner>

<Prescription example 2: Moisturizing gel>

Claims (2)

A skin care cosmetic containing the following ingredients (A) to (C).
(A) Compound represented by the following formula (I): 0.01 to 0.7% by mass

(In formula (I), R ¹ and R ² are the same or different groups and represent alkyl groups having 14 to 22 carbon atoms.)
(B) Surfactin represented by the following formula (II) or a salt thereof: 0.01 to 0.7% by mass

(In the formula, * represents an optically active point. X represents an amino acid structure selected from leucine, isoleucine, and valine, R represents an alkyl group having 9 to 13 carbon atoms, and M represents a hydrogen atom and an alkali. Represents a metal atom, an alkaline earth metal atom, or an optionally substituted ammonium.)
(C) 2-Tetravalent polyhydric alcohol having 3 to 6 carbon atoms: 0.1 to 15% by mass The skin care cosmetic according to claim 1, which contains 0.001 to 0.05% by mass of an oil agent liquid at 25 ° C. as the component (D).