KR101821207B1

KR101821207B1 - Solubilization cosmetic composition containing oleanolic acid

Info

Publication number: KR101821207B1
Application number: KR1020100116288A
Authority: KR
Inventors: 피봉수; 박성일; 하정철; 김연준; 한상훈
Original assignee: (주)아모레퍼시픽
Priority date: 2010-11-22
Filing date: 2010-11-22
Publication date: 2018-01-24
Also published as: WO2012070804A2; JP2016222694A; KR20120054906A; JP6321962B2; HK1186963A1; SG190131A1; JP2013542984A; CN103221028B; WO2012070804A3; JP6231624B2; CN103221028A

Abstract

The present invention relates to a cosmetic composition for solubilization using oleanolic acid collected in a nanoliposome as an active ingredient. By using a nanoliposome, the percutaneous absorption rate of an effective ingredient is increased, promoting the synthesis of collagen and thus providing an excellent wrinkle- Since no other additional raw material is used for encapsulation, the manufacturing cost of the product can be reduced and an excellent feeling of use can be provided.

Description

[0001] The present invention relates to a cosmetic composition containing oleanolic acid (Solubilization cosmetic composition containing oleanolic acid)

The present invention relates to a solubilized cosmetic composition containing oleanolic acid captured in a nanoliposome as a wrinkle-improving active ingredient.

Skin is the primary barrier of the human body and protects the internal organs of the body from changes in temperature and humidity, from external stimuli such as ultraviolet rays and pollutants, and plays an important role in the maintenance of body homeostasis such as body temperature control. However, excessive physical and chemical stimuli and stress from outside, nutritional deficiency, etc., deteriorate the normal functions of the skin and promote skin aging phenomenon such as loss of elasticity, keratinization and wrinkle formation. The cosmetics conventionally used for maintaining the skin having a problem have many problems such as being insufficient in efficacy or causing side effects of skin (Patent Document 10-2010-0064451).

Research has been actively conducted on raw materials having an anti-aging effect without inducing skin side effects, and it has been found that oleanolic acid is applied to a skin cosmetic composition to exhibit an excellent anti-aging effect. An oleanolic acid, a kind of hydroxypentacyclopentenes, is an active ingredient in many natural plants such as Eriobotrya japonica (loquata), Perilla frutescens, and Staphyleaholocarpa, and is also found in fruits such as apples or pears. It has pharmacological effects such as anti-inflammatory, anti-cancer, anti-allergic, anti-depressive, and antibacterial and antifungal effects. Especially, it has anti-inflammatory and anti-irritation effects related to skin physiological activity. In addition, as an anti-aging function, it promotes the synthesis of procollagen which is important for collagen production, promotes the synthesis of ceramides and pillar green important for preventing aging, inhibits the activity of MMP-1, an enzyme that destroys polymer proteins such as collagen It is characterized by having a dual anti-aging system that promotes collagen production and prevents destruction. Oleanic acid, which has excellent effect for improving skin wrinkles, has been used as a wrinkle improving raw material in various cosmetic formulations of the oil, but it is not only hardly soluble in water, but also has a certain amount Or more. Especially, due to such poor solubility properties, it has been impossible to directly use oleanolic acid as a raw material for improving wrinkles in a solubilized formulation such as a lotion.

Recently, encapsulating oleanolic acid component with 100-150 nm size nanoemulsion using skin lipid-like composition nanotechnology and secondary encapsulation with polymeric emulsifier using inulin, a natural polysaccharide, to improve stability, and to use oleanolic acid regardless of cosmetic formulation However, in the case of emulsified products, it is troublesome to inject the encapsulated oleanolic acid at a temperature lower than 50 ° C and a low homo-mixing rate in order to prevent destruction of the capsules according to the manufacturing process when the encapsulated oleanolic acid is added to the formulation. In the solubilization formulations, stability and potency is still present. Not only is it more expensive than simply using oleanolic acid, but it can also have an adverse effect on product feelings as it uses additional ingredients other than oleanolic acid for encapsulation of oleanolic acid.

In addition, while the organic cosmetics market is growing globally, oleanolic acid is considered to be the only natural wrinkle-functioning ingredient. However, when encapsulating oleanolic acid using the above-mentioned skin lipid-like composition nanotechnology, Can not be used as an organic certified cosmetic ingredient because it contains many ingredients that can not be used in cosmetics.

The object of the present invention is to provide a cosmetic composition for use in a solubilization formulation in which oleanolic acid having excellent wrinkle-reducing effect is stably trapped in a nanoliposome alone without being encapsulated with another additional raw material The purpose.

In order to achieve the above object, the present invention provides a cosmetic composition comprising oleanolic acid captured in a nanoliposome as an active ingredient.

INDUSTRIAL APPLICABILITY The cosmetic composition of the present invention is capable of absorbing oleanolic acid, which is effective for improving skin wrinkles, on the nanoliposome and stabilizing it in the formulation, thereby increasing the rate of percutaneous absorption by the nanoliposome and promoting the synthesis of collagen to provide an excellent wrinkle- So that the manufacturing cost of the product can be reduced. It can also provide a fresh feeling of moisture after absorption, and it can meet the consumer demand for cosmetics with organic wrinkles that are increasing worldwide.

The present invention provides a cosmetic composition containing oleanolic acid as an active ingredient, and the cosmetic composition can be formulated in a solubilized form. The oleanolic acid is trapped in the nanoliposome and can be stabilized by the nanoliposome, thereby increasing the stability and solubility of the oleanolic acid in the solubilized formulation and increasing the percutaneous absorption rate.

The oleanolic acid used in the present invention is recognized as a naturally occurring wrinkle functional ingredient. In the present invention, the oleanolic acid is contained in an amount of 0.0001 to 5.0% by weight, preferably 0.0005 to 1.0% by weight based on the total weight of the composition. At a concentration of less than 0.0001% by weight, no significant effect could be expected, and at a concentration of more than 5.0% by weight, not only the apparent increase in the effect was not observed but the formulation stability was adversely affected.

The nanoliposome formed when the solubilization cosmetic composition of the present invention is prepared is a liposome having a shape of liposome and having an average particle diameter of 10 to 500 nm. The size of the nanoliposome formed in the present invention is preferably 50 to 300 nm . When the average particle diameter of the nanoliposome exceeds 300 nm, improvement of skin penetration and improvement of formulation stability among the technical effects to be achieved in the present invention is very weak.

In the present invention, nanoliposomes formed for the stabilization of oleanolic acid are prepared by a mixture comprising a polyol, an oily component, a surfactant, a phospholipid and water. In addition, the nanoliposome capturing oleanolic acid contained in the solubilization cosmetic composition is naturally formed when a solubilized cosmetic composition is prepared without high-pressure emulsification or a separate manufacturing process.

The polyol used in the cosmetic composition for solubilization containing the nanoliposome of the present invention is not particularly limited, and preferable examples thereof include propylene glycol, dipropylene glycol, 1,3-butylene glycol, glycerin, methylpropanediol, At least one selected from the group consisting of isopropylene glycol, pentylene glycol, erythritol, xylitol, sorbitol, and mixtures thereof. The polyol is used in an amount of 5 to 50% by weight, preferably 15 to 30% by weight, based on the total weight of the solubilized cosmetic composition containing nanoliposome.

The oily component used in the cosmetic composition for cosmetics containing the nanoliposome of the present invention may be selected from various oils known in the art and is preferably a hydrocarbon oil such as hexadecane and paraffin oil, Vegetable oils such as silicon oil such as dimethicone and cyclomethicone, sunflower oil, corn oil, soybean oil, avocado oil, sesame oil and fish oil, ethoxylated alkyl ether oils, propoxylated alkyl ether oils , phytosphingosine, seuping a high signal and a scan non-ping the same scan pinggo cannabinoid lipid, cholesterol side-by celebrity, sitosterol cholesteryl sulfate, cholesteryl sulfate, cytokines, C ₁₀ _-40 fatty alcohols and mixtures thereof. The amount thereof is 0.01 to 10.0% by weight, preferably 1.0 to 5.0% by weight, based on the total weight of the solubilized cosmetic composition comprising the nanoliposome.

Any surfactant known in the art can be used as the surfactant used in the solubilization cosmetic composition containing the nanoliposome of the present invention. For example, in the present invention, an anionic surfactant, a cationic surfactant, a positive surfactant, and a nonionic surfactant can be used as the surfactant, and an anionic surfactant and a nonionic surfactant can be preferably used . Specific examples of anionic surfactants include alkyl acyl glutamates, alkyl phosphates, alkyl lactylates, dialkyl phosphates and trialkyl phosphates. Specific examples of nonionic surfactants include polysorbates, alkoxylated alkyl ethers, alkoxylated alkyl esters, alkylpolyglycosides, polyglyceryl esters and sugar esters. The amount of the surfactant to be used is 0.001 to 5.0% by weight, preferably 0.1 to 1.0% by weight based on the total weight of the solubilized cosmetic composition comprising the nanoliposome.

In the nanoliposome formed in the present invention, the phospholipid is an amphiphilic lipid, in which both affinity lipids are used, and a natural phospholipid (e.g., egg yolk lecithin or soy lecithin, sphingomyelin) and a synthetic phospholipid (e. G., Dipalmitoyl phosphatidylcholine or hydro &Lt; / RTI > generic lecithin), preferably lecithin. In particular, unsaturated lecithin or saturated lecithin derived from natural origin extracted from soybean or egg yolk is preferable. Normally, the amount of phosphatidylcholine is 23 to 95% and the amount of phosphatidylethanolamine is 20% or less in natural derived lecithin. In the preparation of the cosmetic composition for solubilization containing the nanoliposome of the present invention, the amount of the phospholipid to be used is 0.01 to 5.0% by weight, preferably 0.5 to 2.0% by weight based on the total weight of the solubilizing cosmetic composition.

The water used in the solubilizing cosmetic composition containing the nanoliposome of the present invention is generally deionized distilled water, and the amount of water used is 25.0 to 90.0% by weight based on the total weight of the solubilizing cosmetic composition.

The solubilized cosmetic composition of the present invention can be used as an anti-aging composition that provides a particularly excellent wrinkle-reducing effect by containing oleanolic acid.

In addition, the composition of the present invention is not particularly limited in its formulation, but it is preferable to use a cosmetic composition such as a softening agent, a nutrient lotion, a spray, a mist or a gel in consideration of the appearance of a transparent or suspension liquid and advantages in use. A hair cosmetic composition such as a hair tonic, a hair essence or a hair treatment; It can be widely applied to other medicines and quasi-drugs and can be used as a skin wrinkle remedy which is safe and effective without side effects even when it is applied to human skin.

The composition of the present invention can be used as a lubricant, a lubricant, a thickening agent and a gelling agent, a softener, an antioxidant, a suspending agent, a stabilizer, a foaming agent, a fragrance, a surfactant, water, In the field of cosmetics or dermatology, such as ionic sequestering and chelating agents, preservatives, vitamins, blockers, moisturizers, essential oils, dyes, pigments, hydrophilic or lipophilic active agents, lipid vesicles or any other ingredient commonly used in cosmetics And may contain commonly used adjuvants. These adjuvants are introduced in amounts commonly used in the cosmetic or dermatological fields.

Hereinafter, the present invention will be described in more detail with reference to examples and test examples. However, it should be understood that the following Examples, Experimental Examples and Preparation Examples are provided for illustrative purposes only in order to facilitate understanding of the present invention, but the scope and scope of the present invention are not limited thereto.

[Reference Example 1] Manufacture of liposome-stabilized oleanolic acid-soluble cosmetic lotion

The solubilized lotion for improving wrinkles of Examples 1 to 3 and Comparative Examples 1 to 4 was prepared according to the composition shown in Table 1 below (unit: wt%).

Examples 1 to 3 are solubilized lotion containing the nanoliposome at the same time as forming the nanoliposome according to the present invention. Comparative Examples 1 to 2 use general solubilizers different from Examples 1 to 3, Comparative Example 3 Contains oleanolic acid in the form of an encapsulated oleanolic acid nano-base. In Comparative Example 4, oleanolic acid was dissolved in a mixture of ethanol and propylene glycol in a 4: 1 ratio.

ingredient Example 1 Example 2 Example 3 Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 One Hydrogenated lecithin 0.05 0.2 1.0 - - 0.2 - 2 PIGGY-60 Hydrogenated Castor Oil - - - 1.8 - - - 3 Caprylic / caprylic glucoside - - - - 3.6 - - 4 Propylene glycol 25 25 25 25 25 25 20 5 glycerin 4.00 4.00 4.00 4.00 4.00 4.00 - 6 Dicaprylyl carbonate Suitable amount Suitable amount Suitable amount Suitable amount Suitable amount Suitable amount - 7 Oleanolic acid 0.05 0.05 0.05 0.05 0.05 - 0.05 8 Preservative Suitable amount Suitable amount Suitable amount Suitable amount Suitable amount Suitable amount - 9 incense Suitable amount Suitable amount Suitable amount Suitable amount Suitable amount Suitable amount - 10 ethanol 4.0 4.0 4.0 4.0 4.0 4.0 Balance 11 Purified water Balance Balance Balance Balance Balance Balance - 12 Dermofeel PA-3 0.02 0.02 0.02 0.02 0.02 0.02 - 13 Betaine 2.00 2.00 2.00 2.00 2.00 2.00 - 14 Xanthan gum 0.2 0.2 0.2 0.2 0.2 0.2 - 15 The encapsulated oleanolic acid nano-base
(Including 0.05 wt% of pure oleanolic acid) - - - - - 2.5 -

The manufacturing method is as follows.

1) Components 1 to 3 and components 4 to 5, which are polyols, were added all at once and heated to 80 ° C to dissolve them. Components 6 to 9 were then added and mixed uniformly.

2) The mixture of 1) was cooled to 65 ° C, and ethanol (Component 10) was added thereto and sufficiently mixed.

3) The water phase components of components 11 to 14 were homogeneously mixed in advance, heated to 65 DEG C and then homogeneously mixed with the mixture of 2).

4) The above 3) was cooled to room temperature and stored.

On the other hand, in the case of Comparative Example 3, the encapsulated oleanolic acid nano-base (Component 15) is added after Step 3).

[Test Example 1] Evaluation of stability of composition

In order to examine the stability of the cosmetic composition for wrinkle improvement according to the change with time, the solubilized lotion prepared in Examples 1 to 3 and Comparative Examples 1 to 4 was kept at room temperature, 45 ° C in a thermostatic chamber and at -10 ° C to 45 ° C And stored for 1 month in a thermostat circulating at intervals of 12 hours.

Item Types of surfactants [solubilizers] Average particle size (nm) Stability Room temperature 45 ° C cycle Next day 1 week 4 weeks Next day 1 week 4 weeks Next day 1 week 4 weeks Example 1 Hydrogenated Lecithin 0.05% 376 Good Good detach Good detach detach Good Good detach Example 2 Hydrogenated Lecithin 0.20% 257 Good Good Good Good Good Good Good Good Good Example 3 Hydrogenated Lecithin 1.00% 234 Good Good Sedimentation Good Good Sedimentation Good Good Sedimentation Comparative Example 1 Piggy-60 Hydrogenated castor oil 1.80% 245 detach - - detach - - detach - - Comparative Example 2 Caprylic / caprylic glucoside 3.60% 241 detach - - detach - - detach - - Comparative Example 3 Hydrogenated Lecithin 0.20% 240 Good Good Good Good Good detach Good detach -

From the results in Table 2, it can be seen that Examples 1 to 3, in which oleanolic acid was captured on a nanoliposome, are more stable over the long term than Comparative Examples 1 to 2 using other general solubilizing agents. In comparison between Example 2 and Comparative Examples 1 and 2, it was found that the amount of the surfactant used in Example 2 in which oleanolic acid was captured and stabilized in the nanoliposome was much smaller than the amount of the surfactant used in Examples 1 and 2 . It can be seen that when the nanoliposome is formed to capture oleanolic acid, the amount of the surfactant to be used in the formulation can be significantly reduced, and the risk of skin irritation when a large amount of surfactant is used can be avoided.

[Test Example 2] Comparison of the feeling of using a composition prepared by stabilizing oleanolic acid and encapsulated oleanolic acid by forming a nanoliposome

In order to evaluate the feeling of use in Example 2 and Comparative Example 3, a sensory test was conducted on the cosmetic composition for wrinkle-removing prepared in Example 2 and Comparative Example 3. [ Twenty women aged 25 to 35 were applied to the skin of the back of the hand according to the general usage method to evaluate their satisfaction with the feeling of use. (10 points), Excellent (7.5 points), Average (5 points), Poor (2.5 points) and Very poor (0 point) for each item. ), And these values are averaged to be shown in Table 3 below.

Feeling item Example 2 Comparative Example 3 Stickiness 8.4 3.1 Absorbency 9.8 5.2 Moisturizing property 8.5 8.2 Nutritional 6.9 6.3

Comparing Example 2 in which a nanoliposome was formulated to stabilize oleanolic acid and Comparative Example 3 in which encapsulated oleanolic acid was used, Comparative Example 3 in which encapsulated oleanolic acid was used even when the same amount of oleanolic acid was used, When the stability of the nano-liposome was measured, as shown in Table 3, it was found that the stabilizer was used in an amount of about 2.4% by weight or more for the preparation of the oleanolic acid nano-base, And the feeling of use of the formulation stabilized with oleanolic acid is much better.

[Test Example 3] Measurement of promoting effect of collagen biosynthesis

The collagen biosynthesis promoting effect of Example 2 was measured in comparison with tocopherol and EGCG (epigallocatechin gallate; epigallocatechin gallate), which are known to promote collagen biosynthesis. First, human fibroblast (PromoCell, Germany) was seeded in 24 wells at 10 ⁵ per well and cultured until it grew to about 90%. After incubation for 24 hours with Dulbecco's modified Eagle's medium (Dulbecco's modified Eagle's medium) for 24 hours, Example 2, tocopherol and EGCG dissolved in serum-free medium were each treated at a concentration of 10 ^-4 mol, ₂ incubator. These supernatants were released and the procolagen (I) ELISA kit (procollagen type (I)) was used to determine whether procollagen was increased or decreased. The results are shown in Table 4 below, wherein the sum performance is obtained by setting the untreated group to 100.

Treated group Sum performance (%) Example 2 134 Untreated group 100 Tocopherol 113 EGCG 120

As shown in Table 4, the composition of Example 2 promotes collagen biosynthesis, which is far superior to tocopherol and EGCG, which are known to promote collagen biosynthesis.

[Test Example 4] Measurement of skin absorption amount

Skin absorption was measured using a Franz permeable cell against Guinea api skin. Immediately before the test, the skin of the abdomen of Guinea epigae was taken and cut into an area of 1 cm 2 per square, and this was placed in a transmissive cell having a diameter of 0.9 cm and fixed with a clamp. On one side of the skin (donor vessel), samples of Comparative Example 4 in which oleanolic acid was dissolved in ethanol and propylene glycol (4: 1) and Example 2 in which oleanolic acid was stabilized by the formation of nanoliposomes And the other side (receptor vessel) was brought into contact with a solvent mixture of purified water and ethanol in a weight ratio of 4: 1. The temperature during the test was maintained at 32 ° C, which is the actual skin temperature. After the start of the test, a portion of the solvent was collected at intervals of time, and then the amount of oleanolic acid absorbed on the skin was measured by HPLC and expressed as the amount of absorbed skin per application concentration (쨉 g / cm 2 / wt%) And the results are shown in Table 5 below.

Column: Waters Novapak C18 (3.9 mm * 250 mm, 4 um)

- Solvent flow rate: 1 ml / min

- Detection UV: 210 nm

- Sample concentration: 10 ~ 100 ug / mL

- Sample injection volume: 20 uL

- Eluent: MeOH / 0.1% H3PO4 = 82/18

time Example 2 Comparative Example 4 0 0 0 4 16.22 3.52 8 36.13 8.59 16 55.60 10.25

From the results of Table 5, it can be seen that the case of Example 2 in which oleanolic acid is stabilized by the formation of nanoliposome is far superior to that of percutaneous absorption.

Claims

1) a polyol component which is a mixture of propylene glycol and glycerin; C _10-40 fatty alcohol; an oily component; And a phospholipid component that is lecithin to obtain a mixture;
2) adding oleanolic acid to the mixture of step 1);
3) cooling the mixture of step 2), adding ethanol and then uniformly mixing; And
4) adding a surfactant and water to the mixed solution of step 3), and then uniformly mixing the surfactant and water
, Wherein the oleanolic acid is captured.

The method of claim 1, wherein the phospholipid is a hydrogenated lecithin.

The method according to claim 1, wherein the content of lecithin is 0.05 to 1.0 wt% based on the total weight of the composition.

The method according to claim 1, wherein the nanoliposome has an average particle diameter of 50 to 300 nm.

The process according to claim 1, wherein the ratio of oleanolic acid to lecithin is 1: 4 by weight.

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