RETINAL-CONTAINING MULTILAMELLAR VESICLE AND COSMETIC COMPOSITION COMPRISING SAME

Abstract

The present invention relates to a retinal-containing multilamellar vesicle and, more specifically, to a retinal-containing multilamellar vesicle comprising 0.01-5% by weight of retinal, 0.1-10% by weight of rapeseed sterol, 0.1-10% by weight of phytosteryl/behenyl/octyldodecyl lauroyl glutamate, 0.1-8% by weight of polyglyceryl-10 oleate, 0.1-10% by weight of cholesterol, 0.01-5% by weight of hydrogenated lecithin, 0.01-5% by weight of ceramide, 1-15% by weight of squalane, 0.1-10% by weight of vegetable butter, 3-30% by weight of oily liquid, 1-20% by weight of glycerin, and 30-70% by weight of water, and to a cosmetic composition comprising same.

Claims

1. A multilamellar vesicle containing retinal which comprises 0.01 to 5% by weight of retinal, 0.1 to 10% by weight of rapeseed sterol, 0.1 to 10% by weight of phytosteryl/behenyl/octyldodecyl lauroyl glutamate, 0.1 to 8% by weight of polyglyceryl-10 oleate, 0.1 to 10% by weight of cholesterol, 0.01 to 5% by weight of hydrogenated lecithin, 0.01 to 5% by weight of ceramide, 1 to 15% by weight of squalane, 0.1 to 10% by weight of vegetable butter, 3 to 30% by weight of oily liquid, 1 to 20% by weight of glycerin and 30 to 70% by weight of water.

2. The multilamellar vesicle containing retinal according to claim 1, which comprises 0.02 to 4% by weight of retinal, 0.5 to 8% by weight of rapeseed sterol, 0.5 to 8% by weight of phytosteryl/behenyl/octyldodecyl lauroyl glutamate, 0.2 to 7% by weight of polyglyceryl-10 oleate, 0.5 to 8% by weight of cholesterol, 0.05 to 4% by weight of hydrogenated lecithin, 0.05 to 4% by weight of ceramide, 2 to 12% by weight of squalane, 0.5 to 8% by weight of vegetable butter, 4 to 25% by weight of oily liquid, 2 to 18% by weight of glycerin and 35 to 68% by weight of water.

3. The multilamellar vesicle containing retinal according to claim 1, which comprises 0.05 to 3% by weight of retinal, 1 to 7% by weight of rapeseed sterol, 1 to 7% by weight of phytosteryl/behenyl/octyldodecyl lauroyl glutamate, 0.5 to 5% by weight of polyglyceryl-10 oleate, 1 to 7% by weight of cholesterol, 0.1 to 3% by weight of hydrogenated lecithin, 0.1 to 3% by weight of ceramide, 3 to 10% by weight of squalane, 1 to 7% by weight of vegetable butter, 5 to 20% by weight of oily liquid, 3 to 15% by weight of glycerin and 40 to 65% by weight of water.

4. The multilamellar vesicle containing retinal according to claim 1, wherein the vegetable butter is selected from the group consisting of shea butter, cocoa butter, olive butter, macadamia nut butter, coconut butter, almond butter and a mixture thereof.

5. The multilamellar vesicle containing retinal according to claim 1, wherein the oily liquid is selected from the group consisting of safflower oil, sunflower seed oil, jojoba oil, olive oil, tea tree oil, canola oil, castor oil, palm oil, cetyl ethylhexanoate, isocetyl ethylhexanoate, cetyl isononanoate, cetearyl isononanoate, cetearyl nonanoate, ethylhexyl isononanoate, ethylhexyl isostearate and a mixture thereof.

6. The multilamellar vesicle containing retinal according to claim 1, wherein the average diameter of the multilamellar vesicle is 50 to 400 nm.

7. A cosmetic composition comprising the multilamellar vesicle containing retinal according to claim 1.

8. The cosmetic composition according to claim 7, which comprises 1 to 60% by weight of the multilamellar vesicle containing retinal.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0032] FIG. 1 is a schematic diagram showing retinoid metabolism.

[0033] FIG. 2 is a result of measuring the particle diameter size of multilamellar vesicles containing retinal by the use of Photal, ELS-Z.

[0034] FIG. 3 is a result of measuring zeta potential by the use of Photal, ELS-Z to measure the stability of multilamellar vesicles containing retinal.

[0035] FIG. 4 is a cryo-electron microscopy photograph of multilamellar vesicles containing retinal.

[0036] FIGS. 5A, 5B and 5C are graphs representing changes in retinal content measured in the cream of Comparative Example 2 (Cream A) and the cream of Example 4 (Cream B).

DETAILED DESCRIPTION

[0037] Hereinafter, the present invention is explained in more detail with the following examples. However, it must be understood that the protection scope of the present invention is not limited to the examples.

Example 1: Preparation of Multilamellar Vesicle Containing Retinal

[0038] According to the constitutional compositions of Table 1, the ingredients were introduced into a vessel and dissolved at 80° C. The resulting ingredients were mixed by the use of a homo-mixer for 5 minutes and passed three (3) times through a high-pressure homogenizer at 1,000 bar, followed by cooling and deaeration to obtain multilamellar vesicles in which retinal is stabilized.

TABLE-US-00001 TABLE 1 Ingredient Content (% by weight) Retinal 0.1 Rapeseed sterol 3 Phytosteryl/behenyl/octyldodecyl lauroyl glutamate 3 Polyglyceryl-10 oleate 2 Cholesterol 3 Hydrogenated lecithin 0.5 Ceramide 0.2 Squalane 5 Shea butter 3 Safflower oil 5 Cetyl ethylhexanoate 10 Glycerin 7 Distilled water 58.2 Total amount 100

Comparative Example: Preparation of General Liposome containing Retinal

[0039] According to the constitutional composition of Table 2, the ingredients were introduced into a vessel and dissolved at 80° C. The resulting ingredients were mixed by the use of a homo-mixer for 5 minutes and passed three (3) times through a high-pressure homogenizer at 1,000 bar, followed by cooling and deaeration to obtain liposome composition.

TABLE-US-00002 TABLE 2 Ingredient Content (% by weight) Retinal 0.1 Cholesterol 3 Hydrogenated lecithin 0.5 Ceramide 0.2 Squalane 5 Shea butter 3 Safflower oil 5 Cetyl ethylhexanoate 10 Glycerin 7 Distilled water 66.2 Total amount 100

Example 2: Preparation of Toner by Using Multilamellar Vesicle Containing Retinal

[0040] A toner was prepared by the use of multilamellar vesicle containing retinal according to the constitutional composition of Table 3.

TABLE-US-00003 TABLE 3 Ingredient Content (% by weight) Multilamellar vesicle of Example 1 5 1,3-Butylene glycol 7 PEG-1500 5 Hyaluronic acid 1 Natto extract 5 Distilled water 77 Total amount 100

Example 3: Preparation of Lotion by Using Multilamellar Vesicle Containing Retinal

[0041] A lotion was prepared by the use of multilamellar vesicle containing retinal according to the constitutional composition of Table 4.

TABLE-US-00004 TABLE 4 Ingredient Content (% by weight) Multilamellar vesicle of Example 1 15 Polysorbate 20 5 Cetearyl alcohol 0.5 Olive oil 3 Squalane 4 Silicone oil 2 Butylene glycol 5 Carbopol 0.2 Distilled water 65.3 Total amount 100

Example 4: Preparation of Cream by Using Multilamellar Vesicle Containing Retinal

[0042] A cream was prepared by the use of multilamellar vesicle containing retinal according to the constitutional composition of Table 5.

TABLE-US-00005 TABLE 5 Ingredient Content (% by weight) Multilamellar vesicle of Example 1 50 Polyglyceryl-3 Stearate/Citrate 4 Behenyl alcohol 1.5 Safflower oil 5 Sunflower seed oil 3 Dimethicone oil 2 Propylene glycol 8 Carbopol 0.36 Distilled water 26.14 Total amount 100

Comparative Example 2: Preparation of Cream Containing Retinal

[0043] A cream containing retinal was prepared according to the constitutional composition of Table 6.

TABLE-US-00006 TABLE 6 Ingredient Content (% by weight) Retinal undiluted solution 0.05 Polyglyceryl-3 stearate/citrate 4 Behenyl alcohol 1.5 Safflower oil 5 Sunflower seed oil 3 Dimethicone oil 2 Propylene glycol 8 Carbopol 0.36 Distilled water 76.09 Total amount 100

Example 5: Preparation of Essence by Using Multilamellar Vesicle Containing Retinal

[0044] An essence was prepared by the use of multilamellar vesicle containing retinal according to the constitutional composition of Table 7.

TABLE-US-00007 TABLE 7 Ingredient Content (% by weight) Multilamellar vesicle of Example 1 20 Carbopol 0.3 Hyaluronic acid 3 Allantoin 0.1 PEG-1500 3 Calcium hydroxide 0.03 Sodium EDTA 0.05 Propylene glycol 6 Polyglyceryl-3 stearate/citrate 5 Distilled water 62.52 Total amount 100

Experimental Example 1: Measurement of Particle Size Distribution

[0045] The particle size distribution of the multilamellar vesicles containing retinal prepared in Example 1 was measured by the use of Photal, ELS-Z, and the result is represented in FIG. 2. From the result of the measurement, it can be known that the average particle size of the multilamellar vesicles containing retinal is 308.1 nm.

Experimental Example 2: Measurement of Stability of Multilamellar Vesicle Containing Retinal

[0046] To measure the stability of the multilamellar vesicles containing retinal prepared in Example 1, zeta potential was measured by the use of Photal, ELS-Z, and the result is represented in FIG. 3. From the result of the measurement, it can be known that the potential is −63.91 mV, and the multilamellar vesicles are stable.

Experimental Example 3: Electron Microscopy

[0047] Photographs of the multilamellar vesicles containing retinal prepared in Example 1 were taken. Due to very fine particle size, it was impossible to take photographs by a general optical microscope. Therefore, cryo-electron microscopy photographs were taken (FIG. 4). From FIG. 4, it can be known that the multilamellar vesicles are well formed.

Experimental Example 4: Test for Promoting Transdermal Absorption of Multilamellar Vesicle Containing Retinal

[0048] The artificial skin, Neoderm (Tego Science, Korea) was mounted to a Franz-type diffusion cell (Lab Fine Instruments, Korea). 50 mM phosphate buffer (pH 7.4, 0.1M NaCl) was added to a receptor cell (5 mL) of the Franz-type diffusion cell. A diffusion cell was then mixed and diffused at 600 rpm, 32° C., and 50 μL of the multilamellar vesicles of Example 1 and the liposome of Comparative Example 1, respectively, were added to donor cells. Absorption and diffusion were carried out according to the predetermined time, and the area of the skin where the absorption and diffusion were carried out was 0.64 cm.sup.2. After finishing the absorption and diffusion of the active ingredient, the residues—which were not absorbed and remained on the skin—were cleaned with dried Kimwipes™ or 10 ml of ethanol. The skin in which the active ingredient was absorbed and diffused was homogenized by the use of a tip-type homogenizer, and retinal absorbed into the skin was then extracted with 4 ml of dichloromethane. The extract was then filtrated with a 0.45 μm nylon membrane filter. The content of retinal was measured by high-performance liquid chromatography with the following conditions, and the results are represented in Table 8.

TABLE-US-00008 TABLE 8 Transdermal absorption Rate of (μg) increase Multilamellar vesicle of Example 1 0.3822 2-fold Liposome of Comparative Example 1 0.2111 — A) Column: C18 (4.6 × 200 mm, 5 μm) B) Mobile phase: methanol: hexane = 2:1 C) Flow rate: 0.8 mL/min D) Detector: UV 280 nm

[0049] As can be seen from Table 8, it can be known that the multilamellar vesicles of the present invention can deliver retinal into the skin very efficiently.

Experimental Example 5: Analysis of Content Change

[0050] In order to evaluate the stability of retinal to light and temperature, the changes in the content of retinal in the cream of Comparative Example 2 (Cream A) and the cream of Example 4 (Cream B) were analyzed, and the results are represented in FIG. 5. Analysis conditions are the same as in Table 8 above, and HPLC (Model 510 Waters, USA) was used. As can be seen from FIG. 5, it can be known that the multilamellar vesicles of the present invention effectively stabilize retinal.