JPH05255063A - External preparation for skin - Google Patents

Abstract

PURPOSE:To obtain an external preparation for skin preventing deposit of melanin coloring matter, excellently beautifying effects, comprising an alkylsalicylic acid derivative as an active ingredient. CONSTITUTION:The external preparation for skin containing 0.001-20wt.%, preferably 0.01-10wt.% alkylsalicylic acid derivative of the formula (R is 8(Z),11(Z), 14-pentadecatrienyl, 8(Z),11(Z)-pentadecadienyl, 8(Z)-pentadecenyl or pentadecyl) such as 6-[8(Z),11(Z),14-pentadecatrieyl]salicylic acid as an active ingredient. The external preparation for skin prevents deposit of melanin coloring matter after exposure to sunlight and has decoloring effects on skin and excellent safety. The external preparation for skin is prepared in a dosage form such as cream, milky lotion, jelly or pack.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an external preparation for skin which contains an alkylsalicylic acid derivative as an active ingredient and has a significantly improved skin decolorizing effect and is excellent in safety.

[0002]

BACKGROUND OF THE INVENTION Although there are some unclear points regarding the mechanism of skin stains and the like, in general, melanin pigments are formed due to hormonal abnormalities and irritation of ultraviolet rays from sunlight, and this is the skin. It is thought to be abnormally deposited inside. For treating such spots and bruises, a substance that suppresses the production of melanin, for example, a method of administering a large amount of vitamin C, a method of injecting glutathione, etc., or kojic acid, L-
Ascorbic acid, cysteine, etc. are applied in the form of ointments, creams, lotions, etc., and topically applied. However, the fact is that these methods have not yet been sufficiently effective.

In Europe and America, hydroquinone preparations are used as medicines. However, these compounds, except for hydroquinone, are extremely slow in exhibiting their effects, and thus have insufficient whitening effects. On the other hand, the effect of hydroquinone has been acknowledged for the time being, but in general it is sensitizing, so generally,
Limited use. Therefore, in order to improve its safety, attempts have been made to use higher fatty acid monoesters and alkyl monoethers, but the esters are not necessarily safe because they are decomposed by hydrolytic enzymes in the body. In terms of safety, there has not been obtained any kind of product.

[0004]

In view of such circumstances, the present inventors have conducted earnest research on a compound having an excellent whitening effect and an excellent safety, and as a result, alkyl salicylic acids solve these problems. The present invention has been completed and the present invention has been completed.

[0005]

That is, the present invention relates to an alkylsalicylic acid derivative represented by the following general formula 2
The external preparation for skin is characterized by containing one or more species.

[0006]

[Chemical 2]

[Wherein R is 8 (Z), 11 (Z), 14-pentadecatrienyl group, 8 (Z), 11 (Z) -pentadecadienyl group, 8 (Z) -pentadecenyl group , Pentadecyl group. ]

The structure of the present invention will be described in detail below. The alkylsalicylic acid derivative used in the present invention is a known substance such as cashew nut (Anacardium Occidental).
It can be easily prepared by extracting e) with methanol and performing silica gel column chromatography.

Specific examples of substance names include 6- [8 (Z), 11 (Z), 14-pentadecatrienyl] salicylic acid 6- [8 (Z), 11 (Z) -pentadecadi Enyl] salicylic acid 6- [8 (Z) -pentadecenyl] salicylic acid 6-pentadecylsalicylic acid.

The compounding amount is 0.001 to 20% by weight, preferably 0.01 to 10% by weight, based on the total amount of the skin external preparation. If it is less than 0.001% by weight, the whitening effect is poor, and if it exceeds 20% by weight, the effect cannot be expected to increase.

The external preparation for skin of the present invention contains, in addition to the above-mentioned essential components, external preparations for skin such as cosmetics and pharmaceuticals, and other components used for whitening agents such as oils, UV absorbers,
Antioxidants, surfactants, moisturizers, fragrances, water, alcohols, thickeners, coloring materials, skin nutrients (tocopherol acetate,
Pantotenyl, ethyl ether, glycyrrhizinate, etc.) can be appropriately blended as necessary.

[0012]

EXAMPLES Next, the present invention will be described in detail with reference to examples. The present invention is not limited to this. The blending amount is% by weight. Prior to the examples, the effect test method and evaluation method of the present invention will be described.

(1) Whitening effect test (Test method) 70 subjects exposed to sunlight in the summer for 4 hours (2 hours a day for 2 days) were exposed to sunlight on the skin of the upper arm inner part After 5 days, each test amount was applied once in the morning and in the evening for 8 weeks. The panel was divided into 10 groups, and 6 groups were tested by the following formulations.

Samples of Examples 1 to 4 and Comparative Examples 1 and 2 (alcohol phase) wt% 95% ethyl alcohol 55.0 polyoxyethylene (25 mol) hydrogenated castor oil ether 2.0 antioxidant / preservative proper amount perfume proper amount drug ( Table 1) 1.0 (Aqueous phase) Glycerin 5.0 Sodium hexametarate Appropriate amount Ion-exchanged water Residual (Production method) The aqueous phase and alcohol phase are adjusted and solubilized.

(Evaluation method) The lightening effect after use was judged based on the following judgment criteria. (Judgment) ⊚: When the ratio of markedly effective and effective among the subjects is 80% or more ◯: The ratio of markedly effective and effective among the subjects is 50 to 8
In the case of 0% △: The ratio of markedly effective and effective among the subjects is 50 to 3
0% x: When the ratio of markedly effective or effective in the subjects is 30% or less

[0016]

[Table 1] ───────────────────────────────── Compound name Effectiveness ──────── ────────────────────────── Comparative example 1 ────── × Comparative example 2 Hydroquinone △ ────────── ──────────────────────── Example 1 6-Pentadecylsalicylic acid ○ Example 2 6- [8 (Z) -pentadecenyl] ○ Salicylic acid Example 3 6- [8 (Z), 14 (Z)-◎ Pentadecadienyl] salicylic acid Example 4 6- [8 (Z), 14 (Z), 11- ◎ Pentadecatrienyl] salicylic acid ──── ─────────────────────────────

As is clear from Table 1, the effect after exposure to sunlight is greater in Example than in Comparative Example in that excessive deposition of melanin pigment can be prevented and darkening can be prevented. Admitted.

Example 5 Cream Stearic Acid 5.0 Stearyl Alcohol 4.0 Ilpropylmyristate 18.0 Glycerin Monostearate 3.0 Propylene Glycol 10.0 6-Pentadecylsalicylic Acid 20.0 Caustic Potassium 0.2 Sodium Bisulfite 0.01 Preservative Adequate Fragrance Adequate Ion Exchange Water Residual (Production Method ) Propylene glycol and caustic potash are added to ion-exchanged water, dissolved and heated to 70 ° C (aqueous phase). The other ingredients 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 kept for a while to cause the reaction. After that, the mixture is uniformly emulsified with a homomixer and cooled to 30 ° C. with thorough stirring.

Example 6 Cream Stearic acid 6.0 Sorbitan monostearate 2.0 Polyoxyethylene (20 mol) Sorbitan monostearate 1.5 Propylene glycol 10.0 6- [8 (Z) -Pentadecenyl] salicylic acid 5.0 Glycerin trioctanoate 10.0 Squalene 5.0 Sodium hydrogen sulfite 0.01 Ethylparaben 0.3 Fragrance Suitable amount Ion-exchanged water Residual (production method) Propylene glycol is added to ion-exchanged water and heated to 70 ° C (aqueous phase). The other ingredients are mixed, heated and melted and kept at 70 ° C. (oil phase). The oil phase is added to the aqueous phase to carry out preliminary emulsification, and the mixture is homogenized with a homomixer and then cooled to 30 ° C. with thorough stirring.

Example 7 Cream 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 Glycerin monostearate 2.0 Propylene glycol 5.0 6- [8 ( Z), 11 (Z) -Pentadecadienyl] salicylic acid 0.01 Perfume proper amount sodium bisulfite 0.03 ethylparaben 0.3 ion-exchanged water Residual (manufacturing method) Propylene glycol is added to ion-exchanged water and kept at 70 ° C. (aqueous phase) . The other ingredients are mixed, heated and melted and kept at 70 ° C. (oil phase). The oil phase is added to the aqueous phase to carry out preliminary emulsification, and the mixture is homogenized with a homomixer and then cooled to 30 ° C. with thorough stirring.

Example 8 Emulsion 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 6-Pentadecylsalicylic acid 10.0 Sodium bisulfite 0.01 Ethylparaben 0.3 Carboxyvinyl polymer 0.05 (Brand name: Carbopol 941) BF Goodrich Chemical company Fragrance Suitable amount Ion-exchanged water Residue (production method) Carboxyvinyl polymer is dissolved in a small amount of ion-exchanged water (phase A). Polyethylene glycol 1500 and triethanolamine are added to the remaining ion-exchanged water, and the mixture is heated and dissolved and kept at 70 ° C (aqueous phase). The other ingredients are mixed, heated and melted and kept at 70 ° C. (oil phase). The oil phase is added to the aqueous phase to carry out preliminary emulsification, the phase A is added, and the mixture is uniformly emulsified with a homomixer and cooled to 30 ° C. with thorough stirring.

Example 9 Emulsion (oil phase part) Stearyl alcohol 1.5 Squalene 2.0 Vaseline 2.5 Deodorizing 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 ethyl Paraben 0.2 Butylparaben 0.1 6- [8 (Z), 11 (Z), 14-Pentadecatrienyl] 1.0 Salicylic acid Perfume Appropriate amount (water phase part) Sodium hydrogen sulfite 0.01 Glycerin 5.0 Sodium hyaluronate 0.01 Carboxyvinyl polymer 0.2 (Product) Name: Carbopol 941) BF Goodrich Chemical company Potassium hydroxide 0.2 Purified water Residual (manufacturing method) The oil phase part is dissolved at 70 ° C. Aqueous phase 70 ℃
And the oil phase is mixed with the water phase, and the mixture is emulsified with an emulsifier and cooled to 30 ° C. with a heat exchanger.

Example 10 Jelly 95% Ethyl alcohol 10.0 Dipropylene glycol 15.0 Polyoxyethylene (50 mol) Oleyl alcohol ether 2.0 Carboxyvinyl polymer 1.0 (trade name: Carbopol 940) BF Goodrich Chemiacl company Caustic soda 0.15 L-Arginine 0.1 6 -Pentadecyl salicylic acid 0.05 Sodium 2-hydroxy-4-methoxybenzofenone sulfonate 0.05 Methylparaben 0.2 Ethylenediaminetetraacetate ・ 3 sodium ・ 2 water 0.05 Perfume A suitable amount of ion-exchanged water Residual (manufacturing method) Carbopol 940 is evenly added to ion-exchanged water. On the other hand, 1- (4-hydroxyphenyl) -pentadecanol and polyoxyethylene (50 mol) oleyl alcohol ether are dissolved in 95% ethanol and added to the aqueous phase. Then add the other ingredients and then add caustic soda,
Thicken by neutralizing with L-arginine.

Example 11 Serum (Phase A) Ethanol (95%) 10.0 Polyoxyethylene (20) Octyldodecanol 1.0 Methylparaben 0.15 Pantothenyl ethyl ether 0.1 6- [8 (Z) -Pentadecenyl] salicylic acid 0.05 (Phase B) ) Potassium hydroxide 0.1 (Phase C) Glycerin 5.0 Dipropylene glycol 10.0 Sodium bisulfite 0.03 Carboxyvinyl polymer 0.2 (Product name: Carbopol 940) BF Goodrich Chemiacl company Purified water Residue (Production method) Phases A and C are evenly distributed. Dissolves and A in phase C
Add phase and solubilize. Then, phase B is added and filling is performed.

Example 12 Pack Dipropylene glycol 5.0 Polyoxyethylene (60 mol) hydrogenated castor oil 5.0 (Phase B) 6-pentadecylsalicylic acid 1.0 6- [8 (Z) -pentadecenyl] salicylic acid 1.0 6- [8 (Z ), 14 (Z) -pentadecadienyl] salicylic acid 1.0 Olive oil 5.0 Tocopherol acetate 0.2 Ethylparaben 0.2 Perfume 0.2 (Phase C) Sodium bisulfite 0.03 Polyvinyl alcohol (saponification degree 90, degree of polymerization 2,000) 13.0 Ethanol 7.0 Purification Water Residue (Production method) A phase, B phase, C phase are uniformly dissolved,
Phase B is added to the phase to solubilize it. Next, this is added to phase C and then filled.

Example 13 Pack containing powder (alcohol phase) 95% ethanol 10.0 propylene glycol 5.0 6-pentadecyl salicylic acid 9.0 6- [8 (Z), 11 (Z), 14-pentadecatrienyl] salicylic acid 1.0 Fragrance Suitable amount Coloring material (Aqueous phase) Zinc white 25.0 Kaolin 20.0 Methylparaben 0.3 Glycerin 5.0 Ion-exchanged water Residual (Production method) Uniformly adjust the aqueous phase at room temperature. Then, the alcohol phase prepared at room temperature is added and uniformly mixed. The external skin preparations or whitening agents of Examples 5 to 13 were excellent in skin decolorizing effect and safety.

[0027]

The external preparation for skin and the whitening agent of the present invention have excellent whitening and decolorizing effects by preventing the deposition of melanin pigment on the skin after exposure to sunlight.

Claims (1)

[Claims] 1. A skin external preparation containing one or more alkylsalicylic acid derivatives represented by the general formula 1. [Chemical 1] [In the formula, R is 8 (Z), 11 (Z), 14-pentadecatrienyl group, 8 (Z), 11 (Z) -pentadecadienyl group, 8 (Z) -pentadecenyl group, pentadecyl group Represents either ]