JP2008081472A - Skin care preparation - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a skin care preparation excellent in qualities such as usability and stability with time through compounding a substance having wrinkle-ameliorative effect together with specific oil(s). <P>SOLUTION: The skin care preparation comprises (A) a compound of general formula (1) and (B) one or more kinds of oils selected from those having an IOB value of 0.29-1.0, an organicity value of 250-450 and a melting point of 30°C or lower. In general formula (1), when R<SP>1</SP>and R<SP>2</SP>are each H, R<SP>3</SP>is CH<SB>2</SB>CH<SB>3</SB>, while when either one of R<SP>1</SP>and R<SP>2</SP>is acetyl and the other being H, or when R<SP>1</SP>and R<SP>2</SP>are each acetyl, R<SP>3</SP>is CH:CH<SB>2</SB>. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a skin external preparation excellent in quality such as usability and stability over time by blending a substance having an effect of improving wrinkles together with a specific oil.

  As the skin ages, signs of aging such as wrinkles, spots, dullness, and tarmi appear as appearance changes. Of these, researches are proceeding on those that are considered to be caused by pigmentation such as spots and dullness, and various whitening agents have been developed and marketed.

On the other hand, wrinkles (particularly wrinkles generated as a result of the progress of photoaging) are considered to have various causes such as thickening of the epidermis and a decrease in collagen, which is a constituent component occupying most of the dermis. Research on wrinkles caused by such photoaging has also progressed, and several substances having an improving effect have been found. For example, there are vitamin A derivatives and sclareol derivatives disclosed by the applicants in JP-A-2005-336158 (Patent Documents 1 and 2).

However, some substances with wrinkle-improving effects, such as vitamin A derivatives, are unstable to air, light, metal ions, etc., easily discolored, have low solubility, and avoid restrictions on formulation and formulation. There is a substance that can not be. For this reason, improvement of stability has been performed by blending a large amount of oil or blending an antioxidant and a sequestering agent. Moreover, the improvement of stability has also been performed by mix | blending a specific oil component and an oil-soluble antioxidant (patent documents 3, 4).

Against this background, even for sclareol derivatives having a wrinkle-improving effect, sufficient stability over time and usability cannot be obtained simply by blending such a substance into an external preparation for skin or cosmetics. It was a problem that the effect of this could not be demonstrated.
JP 2005-336158 A JP 2005-336147 A JP 2004-123583 A JP-A-6-32720

  Accordingly, an object of the present invention is to provide a skin external preparation excellent in temporal stability and usability of the sclareol derivative represented by the general formula (1) excellent in wrinkle improvement effect.

  As a result of diligent research in view of the above circumstances, the inventors of the present invention have an IOB value of 0.29 to 0.8 in an external preparation for skin containing a sclareol derivative represented by the general formula (1), and are organic. A skin external preparation containing one or more selected from oils having a value of 250 to 450 and a melting point of 30 ° C. or lower has excellent temporal stability and usability, and also has an effect of improving wrinkles. And the present invention has been completed.

（１）
（式（１）中、Ｒ^１、Ｒ^２がともに水素で表される場合、Ｒ^３はＣＨ_２ＣＨ_３であり、Ｒ^１、Ｒ^２のどちらか一方がアセチル基、もう一方が水素で表される場合、または両方がアセチル基で表される場合、Ｒ^３はＣＨ：ＣＨ_２である） That is, claim 1 of the present invention includes (A) a compound represented by the general formula (1), and (B) I
Skin having OB value of 0.29 to 0.8, organic value of 250 to 450, and further containing one or more selected from oils having a melting point of 30 ° C. or lower In topical preparations.

(1)
(Table formula ^(1), if R 1, ^{R 2} are both represented by hydrogen, ^{R 3} is is _CH 2 CH ^_3, either acetyl groups R 1, ^{R 2,} the other is hydrogen Or when both are represented by an acetyl group, R ³ is CH: CH ₂ )

（２） Moreover, Claim 2 of the present invention is the skin external preparation according to Claim 1, wherein the component (A) is hydrogenated sclareol represented by the following structural formula (2).

(2)

（３）
（式（３）中、Ｒ^４は、炭素数１０〜２２、好ましくは１４〜２０の直鎖、又は分岐鎖であるアルキル基、又はアルケニル基で表される。） The third aspect of the present invention is the skin external preparation according to the first or second aspect, wherein the component (B) is a compound represented by the general formula (3).

(3)
(In Formula (3), R ⁴ is represented by a linear or branched alkyl group or alkenyl group having 10 to 22 carbon atoms, preferably 14 to 20 carbon atoms.)

The fourth aspect of the present invention is the skin external preparation according to the first or second aspect, wherein the component (B) is octyldodecyl lactate.

（４）

（５）
（式（４）または式（５）中、Ｒ^５は、炭素数９〜１９、好ましくは１３〜１７の直鎖、又は分岐鎖であるアルキル基、又はアルケニル基で表される。） The fifth aspect of the present invention is the skin external preparation according to the first or second aspect, wherein the component (B) is a compound represented by the general formula (4) or the general formula (5).

(4)

(5)
(In Formula (4) or Formula (5), R ⁵ is represented by a linear or branched alkyl group or alkenyl group having 9 to 19 carbon atoms, preferably 13 to 17 carbon atoms.)

The sixth aspect of the present invention is the skin external preparation according to the first or second aspect, wherein the component (B) is propylene glycol isostearate.

（６）
（式（６）中、Ｒ^６は、炭素数1〜８、好ましくは1〜３の直鎖、又は分岐鎖であるアルキル基、又はアルケニル基で表され、Ｒ^７は、炭素数１〜１９、好ましくは７〜１７の直鎖、又は分岐鎖であるアルキル基、又はアルケニル基で表される。） The seventh aspect of the present invention is the skin external preparation according to the first or second aspect, wherein the component (B) is a compound represented by the general formula (6).

(6)
(In the formula (6), R ⁶ is represented by a linear or branched alkyl group or alkenyl group having 1 to 8 carbon atoms, preferably 1 to 3 carbon atoms, and R ⁷ has 1 to 19 carbon atoms. , Preferably 7 to 17 linear or branched alkyl groups or alkenyl groups.)

The eighth aspect of the present invention is the skin external preparation according to the first or second aspect, wherein the component (B) is lauroyl sarcosine isopropyl.

（７）
（式（７）中、Ｒ^８は、炭素数１〜１９、好ましくは５〜１１の直鎖、又は分岐鎖であるアルキル基、又はアルケニル基で表され、Ｒ^９及びＲ^１０は、それぞれ水素、又は炭素数１〜８、好ましくは１〜４の直鎖、又は分岐鎖であるアルキル基、またはアルケニル基で表される。） The ninth aspect of the present invention is the skin external preparation according to the first or second aspect, wherein the component (B) is a compound represented by the general formula (7).

(7)
(In Formula (7), R ⁸ is represented by a linear or branched alkyl group or alkenyl group having 1 to 19 carbon atoms, preferably 5 to 11 carbon atoms, and R ⁹ and R ¹⁰ are each hydrogen. Or a linear or branched alkyl group having 1 to 8 carbon atoms, preferably 1 to 4 carbon atoms, or an alkenyl group.)

In addition, claim 10 of the present invention is the skin external preparation according to claim 1 or 2, wherein the component (B) is 2-butyl-2-ethyl-1,3-propanediol 2-ethylhexanoate. .

The eleventh aspect of the present invention is the cosmetic skin external preparation according to any one of the first to tenth aspects, further comprising (C) a humectant.

INDUSTRIAL APPLICABILITY The present invention can provide an external preparation for skin that has an effect of improving wrinkles caused by photoaging and is excellent in quality such as usability and stability over time.

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

In this specification, the IOB value is an abbreviation of Inorganic / Organic Balance (inorganic / organic ratio), and is a value representing a ratio of an inorganic value to an organic value, and represents the degree of polarity of an organic compound. It is an indicator to show. Specifically, the IOB value is expressed as IOB value = inorganic value / organic value. Here, for each of the “inorganic value” and “organic value”, for example, “organic value” is 20 for one carbon atom in the molecule, and “inorganic value” is 100 for one hydroxyl group. As described above, “inorganic value” and “organic value” corresponding to various atoms or functional groups are set, and “inorganic value” and “organic value” of all atoms and functional groups in the organic compound. Can be calculated to calculate the IOB value of the organic compound (see, for example, Yoshio Koda, “Organic Conceptual Diagram—Basics and Applications—” pages 11-17, published by Sankyo Publishing, 1984).

Examples of the component (A) sclareol derivative represented by the general formula (1) used in the present invention include hydrogenated sclareol, sclareol monoacetyl, sclareol diacetyl, etc. It is not limited to. These sclareol derivatives can be produced from sclareol commercially available from Tokyo Kasei Kogyo Co., Sigma-Aldrich, etc., or from plant oils containing sclareol obtained from plants. Among these, hydrogenated sclareol is more preferable for obtaining an effect of improving wrinkles and stability over time.

Component (A) used in the present invention The blending amount of the sclareol derivative represented by the general formula (1) is 0.001 to 10.0% by mass (hereinafter simply referred to as “%”) based on the total amount of the external preparation for skin. It is preferably 0.01 to 5.0%. If the blending amount is less than this lower limit, the intended effect of the present invention is not sufficient. On the other hand, even if the upper limit is exceeded, the effect commensurate with the increase is not preferred.

An oil agent having an IOB value of 0.29 to 0.8, an organic value of 250 to 450, and a melting point of 30 ° C. or lower is used as, for example, isostearyl alcohol ( IOB = 0.29; organic value = 350), di-2-ethylhexanoic acid neopentyl glycol (IOB = 0.32; organic value = 380), octyldodecyl lactate (IOB = 0.36; organic value) = 450), propylene glycol oleate (IOB = 0.39; organic value = 420), propylene glycol isostearate (IOB = 0.40; organic value = 410), diethyl sebacate (IOB = 0.43; Organic value = 280), diisopropyl sebacate (IOB = 0.40; organic value = 300), 2-ethyl-2-ethyl-2-ethylhexanoate, -Propanediol (IOB = 0.52; organic value = 310), isostearyl glyceryl ether (IOB = 0.54; organic value = 410), glyceryl monoisostearate (IOB = 0.63; organic value = 410), isopropyl lauroyl sarcosinate (IOB = 0.74; organic value = 350), and the like. Among these, octyldodecyl lactate, propylene glycol isostearate, isopropyl lauroyl sarcosinate, 2-ethyl-2-ethylhexanoate, 2-ethyl-2-ethyl-1,3 for obtaining wrinkle improvement and excellent stability over time -Propanediol is particularly preferred.

The blending amount of the component (B) used in the present invention is not particularly limited, but is 0.1 to 30% based on the total amount of the external preparation for skin from the viewpoint of the effect of improving wrinkles and stability over time. preferable. In particular, 0.5 to 20%, more preferably 1 to 10% is preferable.

In the external preparation for skin of the present invention, a humectant can be further used as the component (C). Such a humectant is not particularly limited as long as it is used in ordinary cosmetics. For example, glycerin, 1,3-butylene glycol, dipropylene glycol, ethylene glycol, 1,4-butylene glycol, diglycerin, triglycerin Examples thereof include polyglycerol such as glycerol, glucose, sorbitol, mannitol, maltose, maltitol, sucrose, fructose, threitol, erythritol, and starch-degrading sugar. Among these, dipropylene glycol is particularly preferable from the viewpoint of usability.

In the external preparation for skin of the present invention, in addition to the above components, oils other than those described above, organic acids, alkalis, surfactants, ultraviolet absorbers, powders, pigments, dyes, as long as the effects of the present invention are not impaired. Ingredients usually used in antiseptic / antifungal agents, antioxidants, chelating agents, thickeners, fragrances, water, and pharmaceuticals, quasi-drugs, cosmetics and the like can be appropriately blended.

The external preparation for skin of the present invention can be produced in accordance with a usual method, for example, any form such as liquid, water-in-oil or oil-in-water emulsion, gel, paste or solid. Can do. In particular, it can be applied to pharmaceuticals, quasi-drugs, cosmetics and the like as a skin external preparation such as lotion, milky lotion, cream, and beauty essence.

EXAMPLES Hereinafter, the present invention will be specifically described with reference to examples, but the present invention is not limited thereto.

Examples 1-12 and Comparative Examples 1-4
According to Table 1, the hydrogenated sclareol of the structural formula (2) was dissolved in each oil agent by the following production method, and the temporal stability of the obtained solution was evaluated by the following method.

(Preparation method)
The blending amount (g) shown in Table 1 was measured into a screw test tube and stirred for 30 minutes while heating at 80 ° C.

(Evaluation method of stability over time)
The samples of Examples 1 to 12 and Comparative Examples 1 to 4 were evaluated by visually confirming the precipitation of crystals under the condition of a 5 ° C. constant temperature layer. The result was determined using the following three-step criteria.

Three-level criteria (average evaluation)
○: Crystal precipitation was not observed until after 1 week.
Δ: Crystallization was observed on the third day after dissolution.
X: Crystallization was observed on the next day after dissolution.

  From Table 1 above, Examples 1 to 12 showed that it was easier to dissolve the compound of the structural formula (2) than Comparative Examples 1 to 4, and was excellent in stability over time.

＊１；ピュアソーム２（日本精化社製）
＊２；ＰＥＭＵＲＥＮ ＴＲ−１（Ｇ．Ｆ．Ｇｏｏｄｒｉｃｈ社製） Examples 13-18 and Comparative Examples 5-6
Cosmetics having the compositions shown in Table 2 were prepared by a conventional method, and the temporal stability of the obtained cosmetics was evaluated by the following method.

* 1: Puresome 2 (Nippon Seika Co., Ltd.)
* 2: PEMUREN TR-1 (manufactured by GF Goodrich)

(Evaluation method of stability over time)
The samples of Examples 13 to 18 and Comparative Examples 5 to 6 were evaluated by confirming the precipitation of crystals under a microscope at 5 ° C. The result was judged using the following three-step criteria.

Three-level criteria (average evaluation)
○: Crystal precipitation was not observed until after 1 week.
Δ: Crystallization was observed on the third day after dissolution.
X: Crystallization was observed on the next day after dissolution.

  From Table 2 above, Examples 13 to 18 were cosmetics with superior temporal stability compared to Comparative Examples 5 to 6.

Example 19, Comparative Example 7
The following test method examined the wrinkle improvement effect when the sample containing the base alone or the hydrogenated sclareol was applied to the photoaged skin.

A group of 10 hairless mice aged 10 weeks at the start of the experimental animal test was used.

2. 2. Measurement of wrinkle improvement effect 2-1. Photoaging conditions and measurement method Photoaging was induced by irradiating UVA and UVB once a day, 5 times a week for 8 weeks. Irradiation dose UVA is increased every ^{20J / cm 2, 25J / cm} 2, 30J / cm 2, UVB and ^{20mJ / cm 2, 30mJ / cm} 2, 40mJ / cm 2 and week, maximum amount after 3 weeks Was irradiated.
The wrinkle improvement effect was evaluated by the wrinkle score. Wrinkle scores were scored according to the method of Bissett et al. (Photochem Photobiol, 46: 367-378, 1987). That is, the size and depth of the wrinkles are comprehensively evaluated with the naked eye, the highest point is 3 points, “large and deep wrinkles can be confirmed” is 3, “wrinkles can be confirmed” is 2, and “wrinkles cannot be confirmed” "Is 1 and" Normal texture is observed "is 0.

2-2. Sample and Experimental Method A cosmetic material having the composition shown in Table 2 was prepared by a conventional method.
First, 0.1 mL of these samples were applied to the back skin of a hairless mouse (diameter: about 2.5 cm) once a day at a frequency of 5 times a week. Applied for a week. And the wrinkle score was scored after completion | finish of application | coating. The wrinkle score was compared using the base application group as a control.

(Wrinkle score evaluation result)
----------------------------
Group Wrinkle score value ------------------------------
Example 19 (Compound 2 compounded sample) Application group 2.44 ± 0.11
Comparative Example 7 (Base Sample) Application Group 2.78 ± 0.09
----------------------------
(Values are mean ± standard error)

  Example 19 showed a significantly lower wrinkle score value as compared with Comparative Example 7, indicating that there was an effect of improving wrinkles induced by photoaging.

Example 20 and Comparative Example 8
The skin creams of Example 20 and Comparative Example 8 shown in Table 4 were used, and a questionnaire survey on (1) wrinkle condition and (2) usability was conducted. The results showed the number of people who answered that they thought so after use compared to before use for each item.

＊３；シリコンＢＹ２２−００８（東レ・ダウ・コーニング・シリコーン社製）

* 3: Silicone BY22-008 (Toray Dow Corning Silicone)

(1) Wrinkle state -----------------------------
Item Number of people
----------------------------
Example 20 Comparative Example 8
----------------------------
Wrinkles are less noticeable 17 6
The size of wrinkles has decreased. 18 5
The number of wrinkles has decreased. 16 4
Increased wrinkles 0 1
----------------------------

(2) Usability -----------------------------
Item Number of people
----------------------------
Example 20 Comparative Example 8
----------------------------
Very good 120
Good 7 3
Unchanged 1 11
Slightly bad 0 5
Bad 0 1
----------------------------

From the results of this test, almost all of the skin creams of Example 20 realized that wrinkles were less noticeable than before use, and the factor was that the size of the wrinkles was reduced rather than the number of wrinkles. I understand. Moreover, the skin cream of Example 20 was almost all people who felt that the feeling of use was very good or good compared to Comparative Example 8.
No skin abnormalities such as irritation and itching with the skin cream of the present invention were observed.

Examples 21-29
A cosmetic having the following composition was produced by a conventional method.

Example 21 (skin lotion)
(Ingredient) (Blending amount%)
Compound of structural formula (2) 0.01
Lauroyl sarcosine isopropyl 1.0
Ethanol 10.0
Polyoxyethylene hydrogenated castor oil (60 EO) 1.0
Monolauric acid polyoxyethylene sorbitan (20E.O.) 0.5
1,3-butylene glycol 4.0
Dipropylene glycol 5.0
Polyoxyethylene methyl glucoside (20E.O.) (* 4) 2.0
Phenoxyethanol 0.3
Oat extract (* 5) 0.2
Dioscorea compositor extract (* 6) 0.1
N-acetylglucosamine (* 7) 0.1
Soymilk fermentation broth (* 8) 0.1
Orange juice (* 9) 0.01
Yeast extract (* 10) 0.01
Seaweed extract (* 11) 0.01
Clove extract (* 12) 0.01
Purified water remaining * 4; Glucam E-20 (Amacoal)
* 5: Awaku extract J (manufactured by Maruzen Pharmaceutical Co., Ltd.)
* 6: Dioscorea compositor root extract (Mitsui Chemicals)
* 7; Marine Sweet F (made by Yaizu Suisan)
* 8: Fermented soymilk (Sansho Pharmaceutical Co., Ltd.)
* 9: Homofruit (orange) N (manufactured by Koei Kogyo Co., Ltd.)
* 10: Dismutin BTJ (Penta Farm)
* 11; Marine purge (Ichimaru Falcos)
* 12: Clove extract (Maruzen Pharmaceutical Co., Ltd.)

Example 22 (milky lotion)
(Ingredient) (Blending amount%)
Compound of structural formula (2) 0.5
2-Ethylhexanoic acid-2-butyl-2-ethyl 1,3-propanediol
1.0
Ethanol 10.0
Hydrogenated soybean phospholipid (* 13) 0.2
Cholesterol 0.1
Cyclopentapolysiloxane 3.0
Octyldodecyl myristate 2.0
1,3-butylene glycol 8.0
Dipropylene glycol 5.0
Concentrated glycerin 2.0
Acrylic acid / alkyl methacrylate copolymer (* 2) 0.1
Carboxyvinyl polymer (* 14) 0.02
Xanthan gum 0.1
Potassium hydroxide 0.05
Edetate disodium 0.02
Phenoxyethanol 0.1
Orchid extract (* 15) 0.3
Pine extract (* 16) 0.3
Okra extract (* 17) 0.3
Olive leaf extract (* 18) 0.2
Hypericum extract (* 19) 0.2
Yuzu extract (* 20) 0.2
Evening primrose extract (* 21) 0.1
Avocado extract (* 22) 0.1
Ghetto leaf extract (* 23) 0.1
Raffinose (* 24) 0.05
L-ascorbic acid sulfate disodium salt (* 25) 0.05
Tea seed extract (* 26) 0.01
Camellia extract (* 27) 0.01
Purified water remaining amount * 13; Cotesome NC-21 (manufactured by NOF Corporation)
* 14: Shintalen L (manufactured by 3V SIGMA)
* 15: Falco Rex Run (made by Ichimaru Falcos)
* 16: Falco rex pine B (Ichimaru Falcos)
* 17: Phytohyaron B (Ichimaru Falcos)
* 18; Olive leaf extract BG (Maruzen Pharmaceutical Co., Ltd.)
* 19: Falco Rex Hypericum B (Ichimaru Falcos)
* 20: Yuzu extract (Maruzen Pharmaceutical Co., Ltd.)
* 21; Luna White B (Maruzen Pharmaceutical Co., Ltd.)
* 22: Falco Rex Avocado B (Ichimaru Falcos)
* 23: Moon peach extract BG (Maruzen Pharmaceutical Co., Ltd.)
* 24: Oligo GGF (Asahi Kasei Kogyo Co., Ltd.)
* 25; VC-SS (manufactured by Nippon Surfactant)
* 26: Tea extract (Maruzen Pharmaceutical Co., Ltd.)
* 27: Camellia seed extract (Maruzen Pharmaceutical Co., Ltd.)

Example 23 (milky lotion)
(Ingredient) (Blending amount%)
Compound of structural formula (2) 1.0
Isostearyl alcohol 3.0
Dipotassium glycyrrhizinate 0.1
Lauroyl-L-glutamate sodium 0.3
Stearic acid 1.0
Lipophilic glyceryl monostearate 1.5
Cholesterol 1.0
Behenyl alcohol 0.5
Vaseline 1.5
Squalane 10.0
Dimethylpolysiloxane 2.0
Xanthan gum 0.1
Bentonite 0.5
1,3-butylene glycol 5.0
Phenoxyethanol 0.5
Elderberry extract (* 28) 0.2
Honoki extract (* 29) 0.2
Extract from licorice (* 30) 0.2
Wheat germ extract (* 31) 0.2
Yokuinin extract (* 32) 0.2
Yukinoshita extract (* 33) 0.2
Honeysuckle extract (* 34) 0.2
Giant extract (* 35) 0.2
Purified water remaining amount * 28; Elderberry extract BG90 (manufactured by Maruzen Pharmaceutical Co., Ltd.)
* 29; Falco Rex Honoki B (Ichimaru Falcos)
* 30: Licorice extract (Maruzen Pharmaceutical Co., Ltd.)
* 31; Clariskin (manufactured by Silab)
* 32: Yokuinin extract BG-S (Maruzen Pharmaceutical Co., Ltd.)
* 33; Yukinoshita extract (manufactured by Ichimaru Falcos)
* 34: Falco Rex Honeysuckle SB (Ichimaru Falcos)
* 35: Ziou extract BG-J (Maruzen Pharmaceutical Co., Ltd.)

Example 24 (milky lotion)
(Ingredient) (Blending amount%)
Compound of structural formula (2) 2.0
G-2-ethylhexanoic acid neopentyl glycol 4.0
Hydrogenated soybean phospholipid (* 13) 2.0
Cholesterol 1.0
Squalane 2.0
Cyclopentapolysiloxane 10.0
Octyl dodecyl myristate 7.0
1,3-butylene glycol 5.0
Dipropylene glycol 5.0
Concentrated glycerin 1.0
Diglycerin 5.0
Polyethylene glycol 4000 3.0
Acrylic acid / alkyl methacrylate copolymer (* 2) 0.1
Carboxyvinyl polymer (* 14) 0.2
Xanthan gum 0.1
Potassium hydroxide 0.08
Edetate disodium 0.02
Phenoxyethanol 0.3
Mevalonolactone (* 36) 0.1
Yeast extract (* 37) 0.1
Hakugai hydrolyzed extract (* 38) 0.1
Mixed plant extract (* 39) 0.1
Carrot extract (* 40) 0.1
Bukuryo extract (* 41) 0.1
Thai Saw Extract (* 42) 0.1
Purified water remaining amount * 36; mevalonolactone (Asahi Denka Kogyo Co., Ltd.)
* 37; East Liquid ZB (Ichimaru Falcos)
* 38: Sina Blanca WH (Technoble)
* 39: Multi-fruit BSC (manufactured by Arch Personal Care Products LP)
* 40: Vegetable collagen (manufactured by Koken)
* 41; Falco Rex Book E (made by Ichimaru Falcos)
* 42; Tissou extract BG-J (manufactured by Maruzen Pharmaceutical Co., Ltd.)

Example 25 (O / W type cream)
(Ingredient) (Blending amount%)
Compound of structural formula (2) 3.0
Propylene glycol oleate 7.0
Lauroyl-L-glutamate sodium 0.5
Monooleic acid polyoxyethylene sorbitan (20EO) 1.0
Polyoxyethylene sorbitan tristearate (20 EO) 1.5
Polyoxyethylene sorbite beeswax (6E.O.) 1.0
Behenyl alcohol 3.0
Lipophilic glyceryl monostearate 1.0
Stearic acid 2.0
Vaseline 3.0
Sara honey bee 1.0
Cetyl palmitate 0.5
Squalane 7.0
Glyceryl tri-2-ethylhexanoate 3.0
Dimethylpolysiloxane 3.0
Maltitol solution 3.0
1,3-butylene glycol 5.0
Dipropylene glycol 5.0
Xanthan gum 0.2
Phenoxyethanol 0.5
Edetate disodium 0.02
Glycine (* 43) 0.01
L-proline (* 44) 0.01
L-alanine (* 45) 0.01
Silk extract (* 46) 0.3
Yeast extract (* 47) 0.1
Palmitoyl pentapeptide (* 48) 0.1
Altea extract (* 49) 0.1
Oolong tea extract (* 50) 0.1
Purified water remaining * 43; Glycine (manufactured by Organic Synthetic Chemical Industries)
* 44; L-proline (Ajinomoto Co., Inc.)
* 45; L-alanine (Ajinomoto Co., Inc.)
* 46; Silk protein extract (Ichimaru Falcos)
* 47; TONISKIN (manufactured by Silab)
* 48; MATRIXYL (manufactured by Croda Japan)
* 49; Altea extract (manufactured by Koei Kogyo Co., Ltd.)
* 50: Oolong tea extract BG (Maruzen Pharmaceutical Co., Ltd.)

Example 26 (O / W type cream)
(Ingredient) (Blending amount%)
Compound of structural formula (2) 0.7
Diethyl sebacate 3.0
Dipotassium glycyrrhizinate 0.1
Hydrogenated soybean phospholipid (* 13) 2.0
Cholesterol 1.0
Behenyl alcohol 3.0
Isostearic acid 2.0
Palmitic acid 0.5
Cetyl palmitate 0.5
Long chain branched fatty acid (12-31) cholesteryl 7.0
Octyldodecyl myristate 2.0
Isocetyl myristate 2.0
Glyceryl triisostearate 1.0
Squalane 5.0
Concentrated glycerin 3.0
Sorbit liquid 3.0
1,3-butylene glycol 5.0
Dipropylene glycol 5.0
Carboxyvinyl polymer (* 14) 0.2
Xanthan gum 0.2
Potassium hydroxide 0.08
Phenoxyethanol 0.4
Edetate disodium 0.02
Dimethylsilanol / hyaluronic acid condensate (* 51) 0.1
Seaweed extract (* 52) 0.1
β-carotene (* 53) 0.001
Gardenia extract (* 54) 0.1
Time extract (* 55) 0.1
Chimp extract (* 56) 0.1
Purified water remaining * 51; DSHC (N) (manufactured by EXSYMOL)
* 52; LAMINAINE-BG (manufactured by Biotech Marine)
* 53: β-carotene (Roche)
* 54: Sanshishi extract BG (Maruzen Pharmaceutical Co., Ltd.)
* 55; Tachiko Sou extract BG (manufactured by Maruzen Pharmaceutical Co., Ltd.)
* 56; Chimp extract BG40 (Maruzen Pharmaceutical Co., Ltd.)

Example 27 (W / O type cream)
(Ingredient) (Blending amount%)
Compound of structural formula (2) 1.0
Isostearyl glyceryl ether 2.0
Poly (oxyethylene oxypropylene) methylpolysiloxane copolymer (* 3)
10.0
Cyclopentasiloxane 10.0
Methylphenyl polysiloxane (* 57) 5.0
Cross-linked silicone powder (* 58) 2.0
Olive oil 5.0
Dipropylene glycol 7.0
Concentrated glycerin 5.0
Sodium chloride 1.0
Magnesium chloride 1.0
Dipropylene glycol 7.0
Methylparaben 0.1
Hydrolyzed conchiolin solution (* 59) 0.1
Assembly extract (* 60) 0.1
Carambola leaf extract (* 61) 0.1
Raspberry extract (* 62) 0.1
Tonin extract (* 63) 0.1
Aloe extract (* 64) 0.1
Purified water remaining * 57; Silicon FZ-209 (Nihon Unicar)
* 58: Trefil E507 (Toray Dow Corning Silicone)
* 59; Pearl protein extract K (Maruzen Pharmaceutical Co., Ltd.)
* 60: Swelltinogen KM (manufactured by Maruzen Pharmaceutical Co., Ltd.)
* 61; Star fruit leaf extract BG30 (Maruzen Pharmaceutical Co., Ltd.)
* 62: Falco Rex Kistrawberry B (Ichimaru Falcos)
* 63; Falco Rex Tonin B (made by Ichimaru Falcos)
* 64; Bellagel Liquid (manufactured by DR Madis Laboratories)

Example 28 (Sunscreen)
(Ingredient) (Blending amount%)
Compound of structural formula (2) 0.5
Glyceryl monoisostearate 2.5
Methylphenyl polysiloxane (* 57) 1.0
Glyceryl tri-2-ethylhexanoate 2.0
2-Ethylhexyl paramethoxycinnamate 3.0
4-tert-Butyl-4′-methoxybenzoylmethane 1.0
2-methoxyhexyl dimethoxybenzylideneoxoimidazolidinepropionate
1.0
Sodium phenylbenzimidazole sulfonate 3.0
Lipophilic glyceryl monostearate 1.0
Sodium polyoxyethylene oleyl ether phosphate (2EO)
0.3
Butylparaben 0.1
Stearoyl-potassium L-glutamate 0.3
Fine particle titanium oxide (* 65) 3.0
Fine zinc oxide (* 66) 7.0
Methylparaben 0.1
Water-soluble collagen solution (* 67) 0.1
Extract from licorice (* 68) 0.1
Purified water remaining * 65; Taipei TTO-55 (A) (Ishihara Sangyo Co., Ltd.)
* 66; ZnO-350 (manufactured by Sumitomo Osaka Cement)
* 67; Neptigen N (manufactured by Maruzen Pharmaceutical Co., Ltd.)
* 68; Ricolex NA (Maruzen Pharmaceutical Co., Ltd.)

Example 29 (Cosmetic liquid)
(Ingredient) (Blending amount%)
Compound of structural formula (2) 0.7
Propylene glycol isostearate 2.0
Ascorbic acid 2-glucoside 2.0
Nicotinamide 1.0
Dipotassium glycyrrhizinate 0.1
Polyoxyethylene sorbitan monooleate (20 EO) 0.3
Polyoxyethylene hydrogenated castor oil (60 EO) 0.5
Ethanol 7.0
Methylphenyl polysiloxane (* 57) 3.0
1,3-butylene glycol 3.0
Polyethylene glycol 1000 1.0
Carboxyvinyl polymer (* 14) 0.1
Potassium hydroxide 0.15
Lactic acid 0.1
Sodium hyaluronate (* 69) 0.01
Royal Jelly Extract (* 70) 0.1
Fragrance 0.01
Purified water remaining * 69; Hyaluronic acid FCH-SU (manufactured by Kibun Food Chemifa)
* 70; Royal Jelly Extract (Api)

The cosmetics obtained in Examples 21 to 29 were all excellent in wrinkle improvement effect, stability over time, and excellent in usability.

In the examples, fragrances having the following fragrance formulations were used.

  The present invention can be used for pharmaceutical preparations, quasi-drugs, cosmetics, etc. as a skin external preparation such as skin lotion, milky lotion, cream, cosmetic liquid, etc. It is possible to provide a skin external preparation excellent in quality such as stability over time, which is very useful from the viewpoint of skin beauty.

Claims (11)

(A) The compound represented by the general formula (1), and (B) an oil agent having an IOB value of 0.29 to 0.8, an organic value of 250 to 450, and a melting point of 30 ° C. or lower. An external preparation for skin comprising one or more selected from the group consisting of: In Formula (1), when R ¹ and R ² are both represented by hydrogen, R ³ is CH ₂ CH ₃ , one of R ¹ and R ² is represented by an acetyl group, and the other is represented by hydrogen. Or when both are represented by acetyl groups, R ³ is CH: CH ₂ .

(1) The skin external preparation according to claim 1, wherein the component (A) is hydrogenated sclareol represented by the following structural formula (2).

(2) Furthermore, the skin external preparation of Claim 1 or 2 whose component (B) is a compound represented by General formula (3). In the formula (3), R ⁴ is represented by a linear or branched alkyl group or alkenyl group having 10 to 22 carbon atoms, preferably 14 to 20 carbon atoms.

(3) The skin external preparation according to claim 1 or 2, wherein the component (B) is octyldodecyl lactate. Furthermore, a skin external preparation of Claim 1 or 2 whose component (B) is a compound represented by General formula (4) or General formula (5). In Formula (4) or Formula (5), R ⁵ is represented by a linear or branched alkyl group or alkenyl group having 9 to 19 carbon atoms, preferably 13 to 17 carbon atoms.

(4)

(5) Furthermore, the skin external preparation of Claim 1 or 2 whose component (B) is a propylene glycol isostearate. Furthermore, the skin external preparation of Claim 1 or 2 whose component (B) is a compound represented by General formula (6). In the formula (6), R ⁶ is represented by a linear or branched alkyl group or alkenyl group having 1 to 8 carbon atoms, preferably 1 to 3 carbon atoms, and R ⁷ has 1 to 19 carbon atoms, Preferably, it is represented by an alkyl group or an alkenyl group that is 7 to 17 linear or branched.

(6) Furthermore, the skin external preparation of Claim 1 or 2 whose component (B) is lauroyl sarcosine isopropyl. Furthermore, the skin external preparation of Claim 1 or 2 whose component (B) is a compound represented by General formula (7).
In the formula (7), R ⁸ is represented by a linear or branched alkyl group or alkenyl group having 1 to 19 carbon atoms, preferably 5 to 11 carbon atoms, and R ⁹ and R ¹⁰ are each hydrogen, Alternatively, it is represented by a linear or branched alkyl group or alkenyl group having 1 to 8 carbon atoms, preferably 1 to 4 carbon atoms.

(7) The external preparation for skin according to claim 1 or 2, wherein the component (B) is 2-butyl-2-ethyl-1,3-propanediol 2-ethylhexanoate. The skin external preparation according to any one of claims 1 to 10, further comprising (C) a humectant.