JP2000086482A - Skin preparation for external use - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a skin preparation for external use excellent in skin beautifying and whitening effects and preventing and improving effects on skin roughening by including an ester derivative (salt) of ornithine. SOLUTION: This skin preparation for external use is obtained by including (A) 0.001-20 wt.%, preferably 0.01-7 wt.% of an ester derivative (salt) of ornithine represented by the formula (R is an alkyl, an aralkyl or an alkenyl) and, as necessary, (B) an oil, an ultraviolet absorber, an antioxidant, a surfactant, a humectant, a perfume, water, an alcohol, a thickener, a colorant, a skin nutrient preparation (e.g. tocopherol acetate) or the like. The ingredient A may be any of the L-, D- and DL-isomers. The ingredient A is obtained by reacting, e.g. ornithine with an alcohol in the presence of an acidic catalyst. Inorganic acid salts such as that of hydrochloric acid, sulfuric acid, phosphoric acid or hydrobromic acid or organic acid salts such as that of acetic acid, lactic acid, maleic acid, fumaric acid, tartaric acid, citric acid, methanesulfonic acid or p- toluenesulfonic acid are cited as the salt of the ingredient A.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to an external preparation for skin,
In particular, the present invention relates to a skin external preparation excellent in skin whitening effect, skin roughness prevention and improvement effects.

[0002]

2. Description of the Related Art Although there are some unclear points about the mechanism of the occurrence of skin spots and the like, melanin pigments are generally formed due to hormonal abnormalities and stimulation of ultraviolet rays from sunlight. It is believed to be abnormally deposited within. As a method for treating such spots and bruises, a method of administering a substance that suppresses the production of melanin, for example, a large amount of vitamin C, a method of injecting glutathione, or the like, or a method of injecting kojic acid, cysteine, etc. into an ointment, cream, lotion, etc. And locally applied.
In the United States and Europe, hydroquinone preparations are used as pharmaceuticals.

[0003]

However, these compounds, except for hydroquinone, exhibit very slow effects, so that their whitening effect is not sufficient. On the other hand, although the effects of hydroquinone have been recognized, their use is generally restricted due to their sensitizing properties.

The present invention has been made to solve the above problems, and has as its object to provide a skin external preparation excellent in skin whitening effect, skin roughening prevention and improvement effects.

[0005]

Means for Solving the Problems As a result of intensive studies, the present inventors have found that an ester form of ornithine and a salt thereof are
The present inventors have recognized that they exhibit a whitening effect more than hydroquinone, and that they have an effect of preventing and improving rough skin, and have completed the present invention.

That is, the present invention is an external preparation for skin, characterized by containing at least one or more of an ester of ornithine represented by the following general formula (I) and a salt thereof.

Embedded image (In the formula, R represents a linear, branched, or cyclic alkyl group, aralkyl group, or alkenyl group.)

[0007]

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The configuration of the present invention will be described below in detail. The ester form of ornithine represented by the above formula (I) used in the present invention may be any of L-form, D-form and DL-form. R in the above formula (I) represents a linear, branched or cyclic alkyl group, aralkyl group or alkenyl group, and specifically, methyl, ethyl, n-propyl, isopropyl, n -Butyl group, isobutyl group, t
tert-butyl group, n-pentyl group, n-hexyl group,
n-heptyl group, n-octyl group, n-nonyl group, n-
Decanyl group, n-dodecanyl group, n-tetradecanyl group, n-hexadecanyl group, n-octadecanyl group, 2
-Ethylhexyl, cyclohexyl, 2-hexenyl, benzyl, isopentyl and the like. Among them, a methyl group having an alkyl group having 1 to 5 carbon atoms is particularly preferable.

The ornithine ester used in the present invention can be synthesized by a usual ester synthesis method.
For example, it can be obtained by reacting ornithine with each alcohol in the presence of an acidic catalyst.

The ester of ornithine obtained as described above may be, if desired, an inorganic acid salt such as hydrochloric acid, sulfuric acid, phosphoric acid, or hydrobromic acid, or acetic acid, lactic acid, maleic acid, fumaric acid, tartaric acid or citric acid. And organic acid salts such as methanesulfonic acid and p-toluenesulfonic acid.

The external preparation for skin of the present invention contains at least one ester of ornithine and a salt thereof obtained as described above. The compounding amount is 0.001 to 20% by weight, preferably 0.01 to 7% by weight, based on the total amount of the external preparation for skin. If the amount is less than 0.001% by weight, the skin whitening effect and the effect of preventing and improving skin roughness are poor, and even if the amount exceeds 20% by weight, an increase in the effect cannot be expected.

The external preparation for skin of the present invention contains, in addition to the above-mentioned essential components, other components which are usually used in external preparations for skin such as cosmetics and pharmaceuticals, for example, oils, ultraviolet absorbers, antioxidants, and interface agents. Activator, moisturizer, fragrance, water, alcohol,
Thickeners, coloring materials, skin nutritional agents (tocopherol acetate, pantothenyl ethyl ether, glycyrrhizinate) and the like can be appropriately compounded as needed.

[0012]

Next, the present invention will be described in more detail with reference to examples. The present invention is not limited by this. The compounding amount is% by weight.

(Examples 1 and 2, Comparative Examples 1 and 2) (Alcohol phase)% by weight 95% Ethanol 25.0 Polyoxyethylene (25 mol) hydrogenated castor oil ether 2.0 Antioxidant / preservative Suitable amount Perfume Appropriate amount Drug (described in Table 1) 1.0 (aqueous phase) Glycerin 5.0 Sodium hexametaphosphate Appropriate amount Ion-exchanged water residue

Next, a test method for evaluating the effect of the present invention and the evaluation method will be described.

(1) Whitening effect testTest method  4 hours (2 hours a day for 2 days) exposed to summer sunlight
Forty subjects were divided into four groups, each group consisting of ten subjects.
Corresponding to Examples 1 and 2 and Comparative Examples 1 and 2, the upper arm of the subject
5 days after sun exposure on the inner skin
Each sample of Examples and Comparative Examples was applied once in the morning and evening for 8 weeks.
Clothed.Evaluation method  Judgment of lightening effect after use based on the following criteria
did. ：: 80% of subjects showed significant and effective
Greater than: Good: The proportion of the test subjects showing excellent and effective was 50-
In the case of 80% Δ: Of the test subjects, the ratio of significant and effective was 30 to
In the case of 50% ×: 30% of subjects showed significant and effective
Less than

Table 1 shows the chemicals corresponding to Examples 1 and 2 and Comparative Examples 1 and 2, and the results of the whitening effect test.

[Table 1] Drug (compound name) Whitening effect Comparative example 1 None × Comparative example 2 Hydroquinone △ Example 1 L-ornithine methyl ester hydrochloride ◎ Example 2 DL-ornithine n-octyl ester dihydrochloride ◎

As is clear from Table 1, the effect of the embodiment after exposure to sunlight is more effective in preventing the melanin pigment from being deposited and preventing the color from turning black in the example than in the comparative example. Was found to be high.

(2) Test for prevention and improvement of rough skinTest method  In the morning, the panel of 20 women was divided into two groups, each group consisting of 10 women.
After washing the face twice in the evening and one night, a panel of one group
Appropriate amount of cosmetic on the left side of the face and appropriate amount of the cosmetic of Comparative Example 1 on the right of the face
On the other side, another group of panels has an appropriate amount of the cosmetic of Example 2
On the left side of the face, apply an appropriate amount of the cosmetic of Comparative Example 1 on the right side of the face.
Test by applying each over 2 weeks
Was.Evaluation method  3 items (moisture of skin, firmness of skin, moisture of the next morning)
The effectiveness was determined based on the following criteria. ：: 80% of subjects showed significant and effective
Greater than: Good: The proportion of the test subjects showing excellent and effective was 50-
In the case of 80% Δ: Of the test subjects, the ratio of significant and effective was 30 to
In the case of 50% ×: 30% of subjects showed significant and effective
Less than

Table 2 shows the results of the evaluation.

[Table 2] Effect Moisturizing skin Firming skin Moisturizing the next morning Comparative Example 1 × × × Example 1 ◎ ◎ ◎ Example 2 ◎ ◎ ◎

As is clear from Table 2, the skin moisture,
It was recognized that the effects of the skin firmness and the moisture of the next morning were better in the example than in the comparative example.

Example 3 Cream% by Weight Stearic Acid 5.0 Stearyl Alcohol 4.0 Isopropyl Myristate 18.0 Glycerin Monostearate 3.0 Propylene Glycol 10.0 L-Ornithine Ethyl Ester Hydrochloride 20.0 Potassium hydroxide 0.2 Sodium bisulfite 0.01 Preservatives Appropriate amount Perfume Appropriate amount Ion-exchanged water Residue (Preparation method) Add propylene glycol and potassium hydroxide to ion-exchanged water, dissolve and heat to 70 ° C (aqueous phase) ). The other components are mixed, heated and melted and kept at 70 ° C. (oil phase). The oil phase is gradually added to the water phase, and after the addition is completed, the temperature is maintained for a while to cause a reaction. Then, emulsify uniformly with a homomixer and mix well with stirring.
Cool to 0 ° C.

Example 4 Cream Weight% Stearic Acid 6.0 Sorbitan Monostearate 2.0 Polyoxyethylene (20 mol) Sorbitan Monostearate 1.5 Propylene Glycol 10.0 DL-Ornithine 2-ethylhexyl Ester hydrochloride 7.0 Glycerin trioctanoate 10.0 Squalene 5.0 Sodium bisulfite 0.01 Ethylparaben 0.3 Perfume Appropriate amount Ion-exchanged water Residue (Preparation method) Ion-exchanged water is dissolved by adding propylene glycol, Heat and maintain at 70 ° C. (aqueous phase). The other components are mixed, heated and melted and kept at 70 ° C. (oil phase). After preliminarily emulsifying by adding an oil phase to a water phase and uniformly emulsifying with a homomixer, the mixture is cooled down to 30 ° C. with good stirring.

Example 5 Cream Weight% Stearyl Alcohol 7.0 Stearic Acid 2.0 Hydrogenated Lanolin 2.0 Squalane 5.0 2-Octyldodecyl Alcohol 6.0 Polyoxyethylene (25 mol) Cetyl Alcohol Ether 3 0.0 Glycerin monostearate 2.0 Propylene glycol 5.0 L-ornithine cyclohexyl ester acetate 0.005 Fragrance Appropriate amount Sodium bisulfite 0.03 Ethyl paraben 0.3 Ion exchange water Residue (Production method) Propylene to ion exchange water Glycol is added and dissolved, and heated to 70 ° C. (aqueous phase). The other components are mixed, heated and melted and kept at 70 ° C. (oil phase). After preliminarily emulsifying by adding an oil phase to a water phase and uniformly emulsifying with a homomixer, the mixture is cooled down to 30 ° C. with good stirring.

Example 6 Emulsion Weight% Stearic Acid 2.5 Cetyl Alcohol 1.5 Vaseline 5.0 Liquid Paraffin 10.0 Polyoxyethylene (10 mol) Monooleate 2.0 Polyethylene Glycol 1500 3.0 Triethanolamine 1.0 DL-ornithine ethyl ester hydrochloride 10.0 Sodium bisulfite 0.01 Ethyl paraben 0.3 Carboxyvinyl polymer 0.05 Perfume Appropriate amount Ion-exchanged water Residue (Preparation method) Carboxyvinyl in a small amount of ion-exchanged water Dissolve the polymer (phase A). Polyethylene glycol 1500 and triethanolamine are added to the remaining ion-exchanged water, dissolved by heating, and kept at 70 ° C. (aqueous phase). The other components are mixed, heated and melted and kept at 70 ° C. (oil phase). The oil phase is added to the water phase to perform preliminary emulsification, the phase A is added, and the mixture is uniformly emulsified by a homomixer. After the emulsification, the mixture is cooled to 30 ° C. with good stirring.

Example 7 Emulsion Weight% (Oil Phase) Stearyl Alcohol 1.5 Squalene 2.0 Vaseline 2.5 Deodorized Liquid Lanolin 1.5 Evening Primrose Oil 2.0 Isopropyl Myristate 5.0 Glycerin Monooleate 2. 0 Polyoxyethylene (60 mol) hydrogenated castor oil 2.0 Tocopherol acetate 0.05 Ethylparaben 0.2 Butylparaben 0.1 L-Ornithine isopropyl ester hydrochloride 1.0 L-Ornithine benzyl ester hydrochloride 1.0 Fragrance Appropriate amount (aqueous phase) Sodium bisulfite 0.01 Glycerin 5.0 Sodium hyaluronate 0.01 Carboxyvinyl polymer 0.2 Potassium hydroxide 0.2 Purified water Residue (Preparation method) Dissolve the oil phase at 70 ° C. The aqueous phase is dissolved at 70 ° C., the oil phase is mixed with the aqueous phase, emulsified by an emulsifier, and then cooled to 30 ° C. by a heat exchanger.

Example 8 Jelly weight% 95% ethanol 10.0 dipropylene glycol 15.0 polyoxyethylene (50 mol) oleyl alcohol ether 2.0 carboxyvinyl polymer 1.0 sodium hydroxide 0.15 L- Arginine 0.1 DL-ornithine methyl ester hydrochloride 2.0 Methyl paraben 0.2 Perfume Appropriate amount Ion-exchange water Residue (Preparation method) A carboxyvinyl polymer is uniformly dissolved in ion-exchange water. On the other hand, in 95% ethanol, DL-ornithine methyl ester hydrochloride, polyoxyethylene (50%) were used.
Mol) oleyl alcohol ether is dissolved and added to the aqueous phase. Then, after adding other components, the mixture is neutralized with sodium hydroxide and L-arginine to increase the viscosity.

(Example 9) Beauty serum weight% (A phase) 95% ethanol 10.0 Polyoxyethylene (20 mol) octyldodecanol 1.0 Methyl paraben 0.15 Pantothenyl ethyl ether 0.1 DL-ornithine ethyl Ester hydrochloride 0.05 (B phase) Potassium hydroxide 0.1 (C phase) Glycerin 5.0 Dipropylene glycol 10.0 Sodium bisulfite 0.03 Carboxyvinyl polymer 0.2 Purified water Residue (Preparation method) A phase , C phase are uniformly dissolved, and A is added to C phase.
Add phases and solubilize. Then, after adding the phase B, filling is performed.

Example 10 Pack Weight% (A phase) Dipropylene glycol 5.0 Polyoxyethylene (60 mol) hydrogenated castor oil 5.0 (B phase) DL-ornithine isopentyl ester hydrochloride 1.0 Olive oil 5.0 Tocopherol acetate 0.2 Ethylparaben 0.2 Fragrance 0.2 (Phase C) Sodium bisulfite 0.03 Polyvinyl alcohol (degree of saponification, degree of polymerization 2000) 13.0 Ethanol 7.0 Purified water residue ( Production method) A phase, B phase, and C phase are each dissolved uniformly,
Add phase B to phase and solubilize. Then, after adding this to phase C, filling is performed.

The skin external preparations obtained in each of the above Examples were all effective in the whitening effect test and the skin roughness prevention and improvement effect tests conducted in Examples 1 and 2.

[0030]

As described above, the external preparation for skin containing the ester form of ornithine and the salt thereof according to the present invention is a novel external preparation for skin having a skin whitening effect and a skin roughening prevention and improvement effect.

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Claims (1)

[Claims] 1. An external preparation for skin comprising at least one ester of ornithine represented by the following general formula (I) and a salt thereof. Embedded image (In the formula, R represents a linear, branched, or cyclic alkyl group, aralkyl group, or alkenyl group.)