JP2009184963A - Makeup cosmetic containing ubiquinone derivative and/or its salt - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a makeup cosmetic making pores as inconspicuous. <P>SOLUTION: This makeup cosmetic includes a ubiquinone derivative expressed by general formula (1) [wherein, R<SP>1</SP>, R<SP>2</SP>are each independently H or a phosphoric acid group and at least one of the R<SP>1</SP>, R<SP>2</SP>is the phosphoric acid group; and (n) is an integer of 1 to 9] or its salt as an active ingredient. <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

  The present invention relates to a makeup cosmetic. More specifically, the present invention relates to the use of a specific ubiquinone derivative or a salt thereof for producing a makeup cosmetic that is difficult to disintegrate by sebum and that makes pores inconspicuous by continuous use. Related to makeup cosmetics.

Makeup is performed mainly by forming a cosmetic film of cosmetics on the skin, but there is a problem that so-called makeup collapse occurs due to various factors.
Cosmetic disintegration is caused by the fact that the cosmetic on the skin flows down due to sweat, the cosmetic itself rises due to the secretion of sebum, and the cosmetic film is removed due to physical friction on the skin. In particular, it is difficult to maintain a beautiful makeup film, such as a small nose or a forehead that is prone to sebum secretion, and that the pores are conspicuous due to sebum accumulated in the pores.

In order to overcome such drawbacks, methods such as blending cosmetic ingredients that absorb sebum have been taken (see Patent Documents 1 and 2), but the cosmetics that adsorbed sebum itself are the cause of kinks. As a result, a satisfactory feeling of use was not obtained. Therefore, it has been desired to develop a new makeup cosmetic that does not easily lose its makeup.
JP 2005-126327 A JP 2006-1873 A

  An object of the present invention is to provide a makeup cosmetic that is less likely to lose its makeup than conventional makeup cosmetics and that makes pores inconspicuous when used continuously.

  As a result of intensive studies to solve the above problems, the present inventors have found that a ubiquinone derivative or a salt thereof reduces the sebum secretion amount and is less prone to makeup collapse than before, so that pores can be continuously used. The present inventors have found that it is possible to obtain a make-up cosmetic that makes the image less noticeable.

The present invention relates to, for example, [1] to [3] below.
[1] A makeup cosmetic comprising a ubiquinone derivative represented by the following chemical formula (1) and / or a salt thereof.

（式中、Ｒ¹およびＲ²は、それぞれ独立して水素原子またはリン酸基を表し、Ｒ¹および
Ｒ²の少なくとも一方はリン酸基であり、ｎは１〜９の整数を表す。）
〔２〕前記ユビキノン誘導体および／またはその塩が、０．０００５〜５０質量％の濃度で含有されていることを特徴とする〔１〕に記載のメイクアップ化粧料。
〔３〕前記式（１）におけるＲ¹およびＲ²の両方がリン酸基であり、かつｎが５〜９であることを特徴とする〔１〕または〔２〕に記載のメイクアップ化粧料。

(In the formula, R ¹ and R ² each independently represent a hydrogen atom or a phosphate group, at least one of R ¹ and R ² is a phosphate group, and n represents an integer of 1 to 9).
[2] The makeup cosmetic according to [1], wherein the ubiquinone derivative and / or a salt thereof is contained at a concentration of 0.0005 to 50% by mass.
[3] The makeup cosmetic according to [1] or [2], wherein both R ¹ and R ² in the formula (1) are phosphate groups, and n is 5 to 9. .

  According to the present invention, there is provided a makeup cosmetic that is less likely to lose its makeup than conventional makeup cosmetics and that makes pores inconspicuous when used continuously.

Hereinafter, the present invention will be specifically described.
The external preparation for skin and cosmetics according to the present invention contain a ubiquinone derivative represented by the following formula (1) or a salt thereof.

ただし式（１）中、Ｒ¹およびＲ²は、それぞれ独立して水素原子またはリン酸基を表し、Ｒ¹およびＲ²の少なくとも一方はリン酸基であり、ｎは１〜９の整数を表す。

However in the formula (1), R ¹ and R ² each independently represent a hydrogen atom or a phosphoric acid group, at least one of R ¹ and R ² is a phosphoric group, n represents an integer of 1-9 To express.

In the formula (1), R ¹ and R ² each independently represent a hydrogen atom or a phosphate group, and at least one of R ¹ and R ² is a phosphate group, preferably R ¹ and R 2 Both ² are phosphate groups. Moreover, in said Formula (1), although n represents the integer of 1-9, from a viewpoint of maintaining practical solubility and skin affinity with sufficient balance, Preferably it is 5-9, More preferably, n is 9. It is. Among these, both R ¹ and R ² are particularly preferably phosphoric acid groups, and n is 9.

  Such a phosphate group-modified ubiquinone derivative (hereinafter also simply referred to as “ubiquinone derivative”) can be obtained by a conventional method. For example, it can be synthesized by reducing a quinone of a ubiquinone prepared in advance to lead to a quinol type, and further adding phosphoric acid to a hydroxyl group by a conventional method. Such a method is disclosed in detail in US Pat. No. 2,962,519.

  In the present invention, the phosphate group-modified ubiquinone derivative salt may be used. The salt of the ubiquinone derivative means that the anion and cation of the phosphate group of the ubiquinone derivative form a salt. Specific examples of such a cation include sodium ion, potassium ion, calcium ion, magnesium ion, Examples include zinc ions and ammonium ions. Among these, sodium ion and potassium ion are more preferable from the viewpoint of blendability into an external preparation for skin, particularly cosmetics.

  The ubiquinone derivative is used alone or in a mixed state with a salt of the ubiquinone derivative. Hereinafter, the ubiquinone derivatives and salts thereof are collectively referred to as “ubiquinone derivative group”.

  The ubiquinone derivative group has significantly higher water solubility than ubiquinones. For example, the solubility of ubiquinone having 10 side chain isoprene units in water is less than 100 ppm at room temperature, but the solubility of the diphosphate is more than 1% by mass. That is, the phosphate group-modified ubiquinone derivative exhibits a water solubility that is well over 100 times that of ubiquinone. Therefore, an aqueous preparation containing a stable and high concentration ubiquinone derivative group can be easily prepared, and there is no concern about precipitation. Moreover, the radical scavenging ability of the ubiquinone derivative group in the aqueous system is higher than that of ubiquinone, and a makeup cosmetic imparted with higher antioxidant ability can be realized.

Method for Preparing Makeup Cosmetic The concentration of the ubiquinone acid derivative and / or salt thereof in the makeup cosmetic need not be particularly limited, and may be set according to the magnitude of the desired effect, but is generally about 0. When the content is 0005% by mass or more, preferably 0.001% by mass or more, more preferably 0.01% by mass or more, a substantial effect can be given. The maximum concentration of the ubiquinone acid derivative and / or salt thereof is not particularly limited, but as a practical preparation, it is 50% by mass or less, preferably 20% by mass or less, more preferably 10% by mass or less. However, a dosage form provided as a solid preparation having a content of 50% by mass or more and a concentrated and dispersed preparation may be prepared so as to have the above concentration at the time of use.

  Furthermore, in the present invention, the above-mentioned ubiquinone derivative or a salt thereof can be combined with an anti-decoration component, that is, another compound having an action of preventing the anti-decoration, if desired. Examples of such components include at least one compound selected from the group consisting of sebum-absorbing powder, film-forming polymer, and astringent substance.

Examples of the sebum-absorbing powder include silicic anhydride, porous silica, fluorine compound-treated powder, and mica.
Examples of the film-forming polymer include cellulose derivatives such as carboxymethyl cellulose and carboxyethyl cellulose, natural polymers such as gum arabic and starch and derivatives thereof; acrylic water-based polymers such as acrylic acid-methacrylic acid copolymer, polyvinyl Examples thereof include synthetic polymers such as pyrrolidone and polyethylene glycol.

  Examples of astringent substances include plant extracts such as cucumber extract, peach leaf extract, carrot extract, ougon extract, sage extract, grapefruit, coffee extract, and hamamelis extract; metal oxides such as titanium oxide, calamine, and zinc oxide. Metal salts such as sea salt, rock salt, zinc chloride, aluminum chloride and ferric chloride; organic acids such as lactic acid, tartaric acid, succinic acid and citric acid.

These cosmetic breakage prevention components are blended so as to be included in the makeup cosmetics in an amount that does not impair the effects of the present invention.
In the present invention, in addition to the above-described components, in addition to the above-described components, components generally used in external preparations for skin or cosmetics can be blended in an amount that does not impair the effects of the present invention. .

  Ingredients that can be blended are not particularly limited. For example, cosmetic raw material standards second edition commentary, edited by Japan Public Standards Association, 1984 (Pharmaceutical Daily News), cosmetic raw materials non-standard ingredients standards, supervised by the Ministry of Health , 1993 (Pharmaceutical Daily Report), Supplement to Cosmetic Raw Material Standards, Supervised by Ministry of Health and Welfare Pharmaceutical Affairs Bureau, Examination Division, 1993 (Pharmaceutical Daily), Permitted by Cosmetic Variety, Supervised by Ministry of Health and Welfare Pharmacy Bureau, 1993 (Pharmaceutical Daily) Ingredients by cosmetic varieties, supervised by Ministry of Health and Welfare Pharmacy Examination Division, 1997 (Pharmaceutical Daily News), Cosmetic Raw Material Dictionary, 1991 (Nikko Chemicals) and New Cosmetic Functional Materials 300, 2002 (CMC Publishing) Carrier, vehicle, or other delivery function agent, preservative, surfactant, moisture retention agent, thickener, fragrance, chelating agent, water, alcohol, antioxidant, bactericidal , It is possible to use all of the cosmetics raw materials, such as colorants and UV absorbers.

  The makeup cosmetic of the present invention is prepared by charging the above-described components so as to have a desired content, and in accordance with the dosage form and form of the makeup cosmetic to be obtained, according to a conventional method, dissolution, mixing, dispersion, etc. Can be manufactured.

  As a dosage form of the makeup cosmetic of the present invention, a general cosmetic form is applied, and examples thereof include a makeup base, solid, liquid or gel foundation, teak, lipstick, concealer, face powder and the like. It is done.

EXAMPLES Hereinafter, although this invention is demonstrated further more concretely based on an Example, this invention is not limited to these Examples. Further, unless otherwise specified, “%” represents mass%.
[Synthesis Example 1] Synthesis of Ubiquinol 30 g of ubiquinone (MW863.36) was dissolved in 300 ml of hexane. While stirring the solution at room temperature, 300 ml of a 10% (w / v) sodium hyposulfite solution was poured, and the mixture was further stirred at room temperature for 2 hours. The entire amount was transferred to a separatory funnel, and the hexane layer was separated. The remaining aqueous layer was further extracted twice with 50 ml of hexane, and combined with the previously collected hexane layer. The hexane layer was washed 6 times with 50 ml of degassed saturated saline to obtain a transparent hexane layer. Hexane was removed under reduced pressure and then purged with nitrogen all day and night to obtain 29.5 g of a cream colored solid.

[Synthesis Example 2] Synthesis of ubiquinol-1,4-diphosphate tetrapotassium salt 3 g of the solid obtained in Synthesis Example 1 was dissolved in 10 ml of pyridine. The solution was added in a cryogen (salt / ice) bath (−15 ° C.), a solution prepared by dissolving 3.19 g of phosphorus oxychloride in 5 ml of pyridine was added dropwise, stirred for 30 minutes under cooling, returned to room temperature, and further stirred for 2 hours. did. After the solution was removed under reduced pressure, the obtained oil was suspended in 300 ml of diethyl ether, 150 ml of saturated brine was added, the whole amount was transferred to a separatory funnel, left to stand after shaking and stirred, and the ether layer was separated. 120 ml of diluted hydrochloric acid (concentrated hydrochloric acid: water = 1: 2) was added to the obtained ether layer for washing, and then anhydrous magnesium sulfate was added for dehydration. The solution was removed under reduced pressure to give 2.5 g of a yellow oil. 30 ml of methanol was added and dissolved therein, and then a solution prepared by dissolving 0.547 g of potassium hydroxide in 2 g of methanol was added dropwise. The organic solvent was removed under reduced pressure, and further purged with nitrogen all day and night to obtain 2.63 g of a slightly yellow powder. The obtained yellow powder was subjected to NMR measurement and mass spectrometry, and confirmed to be ubiquinol-1,4-diphosphate tetrapotassium salt.

[NMR]
Apparatus: Burker Advance-500
¹ H-NMR (D ₂ O): δ = 1.4 to 1.65 ppm (11H), 1.8 to 1.9 ppm (9H), 1.9 to 2.0 ppm (10H), 2.2 to 2 .4 ppm (3H), 3.8-4.0 ppm (6H), 4.95-5.1 ppm (10H)
³¹ P-NMR (D ₂ O): δ = 1.0-1.2 ppm
(Mass spectrometry)
FAB-MS (−): 1023 (= [M−H] ⁻ )
<Method>
Method: Directly introduced FAB-MS Method apparatus: JEOL JMS-SX102A
FAB matrix: Glycerin scan range: m / Z 50-200
[Example 1]
A 1% liquid foundation was prepared according to the following formulation.

［比較例１］
上記実施例１の処方よりユビキノール−１，４−ジリン酸４カリウム塩を除いた液状ファンデーションを調製した（陰性コントロール）。 <Ingredients>

[Comparative Example 1]
A liquid foundation was prepared by removing ubiquinol-1,4-diphosphate tetrapotassium salt from the formulation of Example 1 (negative control).

[Test Example 1]
<Use target and observation period>
The liquid foundation prepared in Example 1 and Comparative Example 1 was used for 10 weeks by women in their 20s (subjects 1 to 10) for 4 weeks.

<How to use>
In accordance with daily makeup, the foundation of Example 1 was used on one face and the foundation of Comparative Example 1 on the other. In addition, each subject was made not to know which side of the test area was left or right.

<Measurement of effect>
After 4 weeks, the right, left, and no difference were answered as to which of the left and right sides of the face was difficult to collapse and whether the pores were inconspicuous. The case where the foundation administration group side of Example 1 was excellent was rated as 5 points, the case where there was no difference between them was 3 points, and the case where the foundation administration group of Comparative Example 1 was excellent was rated as 0 points. If there is no difference in all subjects, the total score is 30 points.

  The results are shown in Table 1.

表１から明らかなように、実施例１のユビキノール−１，４−ジリン酸カリウム塩を配合したメイクアップ化粧料は、化粧崩れがし難く、かつ継続的な使用で毛穴が目立たなくなるという、既存のものより優れた効果を示した。

As is apparent from Table 1, the makeup cosmetic containing the ubiquinol-1,4-diphosphate potassium salt of Example 1 is difficult to break down and the pores are not noticeable with continuous use. The effect was superior to that of

Claims (3)

A makeup cosmetic comprising a ubiquinone derivative represented by the following chemical formula (1) and / or a salt thereof:

(In Formula (1), R < ¹ > and R < ² > represent a hydrogen atom or a phosphate group each independently, R < ¹ >
And at least one of R ² is a phosphate group, and n represents an integer of 1 to 9. )   The makeup cosmetic according to claim 1, wherein the ubiquinone derivative and / or a salt thereof is contained at a concentration of 0.0005 to 50% by mass. The makeup cosmetic according to claim 1 or 2, wherein both R ¹ and R ² in the formula (1) are phosphate groups and n is 5 to 9.