KR20050054012A - Self-assembled polymeric nanoparticles containing coenzyme q10 and skin-care compositions for exteral application, containing the nanoparticles - Google Patents

Abstract

The present invention provides a self-associative polymer nanoparticle and an external skin composition containing the same, in which an insoluble substance coenzyme Q10 is collected and solubilized in an aqueous solution using an amphiphilic polymer having polycaprolactone as a hydrophobic block and polyethylene glycol as a hydrophilic block. It is about. The nanoparticles according to the present invention utilize the self-associability of the amphiphilic polymer, and are easily obtained without undergoing a mechanical process or a special process requiring high energy, and an aqueous solution of the insoluble material coenzyme Q10 using the amphiphilic polymer. Since it is prepared to be uniformly dispersed in the phase, it is applicable to various external formulations including cosmetics, and when applied to the skin, the skin absorption rate may be improved due to the nanonized size.

Description

Self-assembled polymeric nanoparticles containing coenzyme Q10 and skin-care compositions for exteral application, containing the nanoparticles}

The present invention relates to a self-associating polymer nanoparticles containing coenzyme Q10 and a composition for external application for skin containing the same, more particularly amphiphilic with polycaprolactone as a hydrophobic block and polyethylene glycol as a hydrophilic block The present invention relates to a self-associating polymer nanoparticle, in which coenzyme Q10, an insoluble substance, is collected and solubilized in an aqueous solution using a polymer, and an external composition for skin containing the same.

Skin is the body's primary protective film that protects the body from stimulation of external environment such as temperature and humidity changes, ultraviolet rays, and pollutants, and plays an important role in maintaining homeostasis such as body temperature control. However, excessive physical and chemical stimuli from the outside will degrade the normal function of the skin and promote skin aging. In particular, reactive oxygen species mediate skin damage by ultraviolet light and cause skin cancer or photoaging. Thus, various antioxidants and antioxidant enzymes have been used in cosmetics to protect the skin from free radicals. Recently, coenzyme Q10 (Formula 1), a coenzyme in vivo, has been studied as an antioxidant and reported to be depleted for the first time when the skin is exposed to ultraviolet light (Podda M et al ., Free Rad. Biol. And Med. 1998) . , 23: 55-6). In addition, anti-aging and anti-wrinkle action of coenzyme Q10 has been reported (Hoppe U et al ., Biofactors 1999, 9: 371-378).

However, coenzyme Q10 is insoluble in cosmetic bases and is difficult to formulate. Thus, there have been efforts to introduce insoluble coenzyme Q10 into cosmetics.

Recently, nanoemulsification techniques have been developed and used to collect active ingredients in nanometer-sized emulsified particles and apply them to cosmetics. Nanoemulsion particles have the advantage that the emulsion film is broken in the actual application, or absorbed into the skin to destroy the interfacial film of the nanoemulsion particles to release the active ingredient trapped therein at a time, molecules of the emulsifier to form the emulsion film The design also has the advantage of minimizing contact with the outside world. Accordingly, the necessity for nanotechnology to release the active ingredient effectively in actual application through the formulation process in a stable collection of the active ingredient is increasing.

However, in the case of nanoemulsion particles such as liposomes obtained by using a low molecular emulsifier, the emulsion film is very weak and unstable physically and chemically and is easily contaminated and destroyed by salts or charge-bearing organic or inorganic materials, so that it is difficult to apply to various formulations. . In addition, it is very weak against heat and light, so it is unstable for long-term storage, and in order to contain a high concentration of active ingredients, a large amount of emulsifier must be used in proportion to it, which may cause skin irritation due to the emulsifier. It may be.

In order to make up for the shortcomings of the nanoemulsion particles composed of such low molecular emulsifiers, nanoparticles using a hydrophobic core as a polymer instead of lipids have been studied. In most cases, an excess of surfactant is used to disperse the polymer dissolved in the solvent in nano size and to evaporate the solvent to solidify it (Colloids and Surface A 210 (2002) 95-104). However, since colloidal instability due to the small size makes it difficult to manufacture nanoscale, various types of surfactants and stabilizers must be used or added in combination, and a high energy consumption process such as high pressure emulsification is required. .

Thus, the present inventors earnestly studied to overcome the limitations of the conventional method for preparing polymer nanoparticles, and when using an amphiphilic polymer having polycaprolactone as a hydrophobic block and polyethylene glycol as a hydrophilic block, By the associative capacity, it is found that insoluble material coenzyme Q10 can be collected in aqueous solution and nanoparticles without the need for mechanical treatment or special processes requiring high energy, and without the addition of special additives, dispersants and surfactants. The present invention has been completed. In particular, since amphiphilic polymers containing polycaprolactone, which is a biodegradable aliphatic polyester polymer, are used as hydrophobic blocks, they are excellent in biocompatibility, absorbed into the skin without causing irritation to the skin, and safely decomposed in the body to release coenzyme Q10. This can provide sufficient antioxidant and whitening effects of coenzyme Q10.

Accordingly, the first object of the present invention is to provide a method for capturing and coagulating nanoparticles of coenzyme Q10 without undergoing a special process requiring high energy or mechanical treatment in preparing polymer nanoemulsion particles.

It is a second object of the present invention to enhance the transdermal absorption of coenzyme Q10, to provide a safe, biodegradable polymer nanoparticle in the formulation.

A third object of the present invention is to provide self-associating polymer nanoparticles in which coenzyme Q10 is collected and solubilized in an aqueous solution using an amphiphilic polymer having polycaprolactone as a hydrophobic block and polyethylene glycol as a hydrophilic block.

A fourth object of the present invention is to provide an external composition for skin having excellent antioxidant power and whitening effect, containing the self-associating polymer nanoparticles as an active ingredient.

The first and second objects of the present invention described above can be achieved by the third object described above, and the present invention captures coenzyme Q10 using an amphiphilic polymer with self-association to achieve the above objects. , Solubilization.

In the present invention, the amphiphilic polymer having self-association is a biodegradable polycaprolactone (A, Poly (ε-caprolactone) (Formula 2); hereinafter referred to as "PCL") as a hydrophobic polymer, Polyethylene glycol (B, Poly (ethylene glycol) (Formula 3); hereinafter referred to as "PEG" is used.

(Where n is an integer of 2 or more)

(M is an integer of 2 or more.)

The polycaprolactone (A) and polyethylene glycol (B) is most preferably composed of a biblock in the form of AB or a triblock in the form of ABA or BAB, but a multiblock or graft copolymer may be used. The structure does not impose any particular limitation on the production and effect of the nanoparticles. In addition, the hydrophobic polymer is composed of PCL corresponding to a molecular weight of 500 to 100,000 Daltons, preferably 1,000 to 25,000 Daltons, the hydrophilic polymer is a molecular weight of 500 to 100,000 Daltons, preferably 1,000 to 25,000 Daltons It consists of PEG. The composition ratio of such PCL and PEG may be 1: 9 to 9: 1 by weight, more preferably 3: 7 to 7: 3.

The content of coenzyme Q10 collected inside the nanoparticles can be adjusted depending on the purpose and case, and generally in the range of 0.1 to 50% by weight relative to the total weight of the nanoparticles. If the content of coenzyme Q10 exceeds 50% by weight, it is impossible to collect effectively, and the active ingredient may flow out of the particles to aggregate or denature into crystalline form, which may cause discoloration or odor.

As a method of forming self-associating polymer nanoparticles in which coenzyme Q10 is collected in an aqueous solution using the PCL-PEG copolymer proposed in the present invention, a method of dispersing the PCL-PEG copolymer polymer directly in an aqueous solution and then applying ultrasonic waves ; Dispersing or dissolving the polymer in an organic solvent and then extracting or evaporating the organic solvent with excess water; Dispersing or dissolving the polymer in an organic solvent, followed by vigorous stirring using a homogenizer or a high pressure emulsifier and evaporating the solvent; Dispersing or dissolving the polymer in an organic solvent and dialysis with excess water; Or a method of gradually adding water after dispersing or dissolving a polymer in an organic solvent.

Examples of the organic solvent that can be used in the above method include acetone, dimethyl sulfoxide, dimethylformamide, N-methylpyrrolidone, dioxane, tetrahydrofuran, acetic acid, ethyl acetate, acetonitrile, methyl ethyl ketone, and methylene chloride. , A solvent selected from chloroform, methanol, ethanol, ethyl ether, diethyl ether, hexane and petroleum ether or a mixture thereof can be used.

In the polymer nanoparticles of the present invention obtained by the above-described production method, coenzyme Q10 is collected in the hydrophobic core portion of the self-associating polymer particles and hydrophilic polymer chains are oriented on the surface of the particles, so that they can be stably dispersed in the aqueous phase. The dispersed nanoparticles have an average particle diameter of 1 to 1,000 nm, more preferably 10 to 500 nm, depending on the composition of the polymer and the production method.

When the polymer nanoparticles of the present invention are blended into cosmetics, coenzyme Q10 does not directly contact an emulsified product or a skin product, and thus the titer can be preserved in the formulation, and can be applied to various types of cosmetics such as creams, emulsions, and lotions. Can be.

The external preparation composition for skin containing the polymer nanoparticles of the present invention, as can be seen in the test example described below, due to the nanoscaled size, the skin absorption rate of coenzyme Q10 is enhanced, and biocompatibility is excellent and does not cause skin irritation. As it is absorbed into the skin and decomposed in the body to release coenzyme Q10, it exhibits the antioxidant effect of coenzyme Q10 as it is, and is expected to provide sufficient skin whitening and skin improvement effects.

The external preparation composition for skin of the present invention is not particularly limited in its formulation, and it is a softening longevity, astringent longevity, nourishing longevity, nutrition cream, massage cream, essence, eye cream, eye essence, cleansing cream, cleansing foam, cleansing water , Pack, powder, makeup base, foundation, body lotion, body cream, body oil, body essence, body cleanser, hair dye, shampoo, rinse, toothpaste, mouthwash, lotion, ointment, gel, cream, patch, spray Can be formulated.

In addition, in the composition of each formulation, other ingredients other than coenzyme Q10 as skin improvement raw materials may be appropriately selected and blended by those skilled in the art according to the formulation or purpose of use of the cosmetic. If the selected component can be dissolved in an organic solvent in the preparation of the polymer nanoparticles, it may be captured in an amphiphilic polymer together with coenzyme Q10.

Hereinafter, the present invention will be described in more detail with reference to Examples. However, these Examples are only illustrative description of the present invention, and the scope of the present invention should not be construed as being limited to these Examples.

Preparation Examples 1 to 9 Preparation of PCL-PEG Block Copolymer

In this preparation example, the preparation method of the PCL-PEG diblock copolymer used in the following examples is described for reference, and the present invention is not limited to the copolymer described in the preparation example.

PCL-PEG diblock copolymer of the present invention was prepared by ring-opening polymerization of caprolactone monomer. In a glass flask containing hexamethyldisilazine reacted with a hydroxyl group and containing hexamethyldisilazine, quantum methoxy polyethyleneglycol (Formula 4; hereafter referred to as "mPEG") and catalyst Sn (Oct) ₂ (C. Sigma, St. Louis, MO, USA) was added, followed by injection of caprolactone monomer followed by uniform mixing.

Here, the mPEG (Fluka Chemie GmbH, Buchs, Switzerland) is made by replacing one end of the methoxy (methoxy) group is not reactive, only the hydroxyl group at the other end may participate in the polymer.

(M is an integer of 2 or more.)

The flask containing the mixture was connected by a vacuum line, and after removing moisture and the like in a vacuum state and sealing, it was polymerized while standing at 120 ° C. After 24 hours, the polymerized polymer was dissolved in methylene chloride and then recrystallized with excess methanol to obtain pure PCL-PEG double block copolymer.

The molecular weight of the PCL-PEG double block copolymer thus obtained was analyzed using gel permeation chromatography (hereinafter referred to as "GPC"). The GPC used here is the Agilent 110 series (Agilent Technologies, Palo Alto, Calif., USA), which detects polymers with a Refractive Index (RI) detector, and the column has three PLgel columns (300 ?? 7.5). Mm, pore size = 10 ³ , 10 ⁴ , and 10 ⁵ ??), flow rate was 1.0 ml / min, and tetrahydrofuran (THF) was used as the mobile phase.

Preparation Example of PCL-PEG Double Block Copolymer PCL monomer (g) mPEG (g) mPEG Molecular Weight (Daltons) Sn (Oct) ₂ (g) Molecular weight of synthesized PCL-PEG (Daltone) Preparation Example 1 33 66 5,000 0.5  6,900 Preparation Example 2 50 50 5,000 0.5  8,500 Preparation Example 3 60 40 5,000 0.5 11,000 Preparation Example 4 66 33 5,000 0.5 13,500 Preparation Example 5 75 25 5,000 0.5 18,700 Preparation Example 6 80 20 5,000 0.5 24,300 Preparation Example 7 50 50 3,500 0.5  5,400 Preparation Example 8 50 50 2,000 0.5  3,200 Preparation Example 9 50 50 1,000 0.5  1,700

<Examples 1-20> Preparation of coenzyme Q10-containing polymer nanoparticles prepared using PCL-PEG biblock copolymer

PCL-PEG diblock copolymer (total weight average molecular weight = 10,000 Daltons, PCL: PEG weight ratio = 1: 1) and coenzyme Q10 was dissolved uniformly in 50 ml of the organic solvent shown in Table 2, then 50 ml of an aqueous solution The nanoparticles were formed by spontaneous self-association process. Following the organic solvent removal method shown in Table 2, after removing the organic solvent through a method such as evaporation or dialysis, an aqueous solution of nanoparticles containing coenzyme Q10 was obtained. Preparation conditions of the coenzyme Q10-containing polymer nanoparticles are shown in Table 2 below.

Type and amount of amphiphilic polymer Coenzyme Q10 Organic solvents used Removal method of organic solvent Example 1 Preparation Example 1, 1.5 g 0.5g Acetone evaporation Example 2 Preparation Example 1 1.8 g 1.2 g Acetone evaporation Example 3 Preparation Example 1, 5.0 g 2.5g Acetone evaporation Example 4 Preparation Example 2, 1.5 g 0.5g Acetone evaporation Example 5 Preparation Example 2, 1.8 g 1.2 g Acetone evaporation Example 6 Preparation Example 2, 5.0 g 2.5g Acetone evaporation Example 7 Preparation Example 3, 1.5 g 0.5g Acetone evaporation Example 8 Preparation Example 3 1.8 g 1.2 g Acetone evaporation Example 9 Preparation Example 3, 5.0 g 2.5g Acetone evaporation Example 10 Preparation Example 4 1.8 g 1.2 g Acetone evaporation Example 11 Preparation Example 4 1.8 g 1.2 g Dimethyl sulfoxide dialysis Example 12 Preparation Example 4 1.8 g 1.2 g Dimethylformamide dialysis Example 13 Preparation Example 4 1.8 g 1.2 g Acetonitrile dialysis Example 14 Preparation Example 4 1.8 g 1.2 g Tetrahydrofuran dialysis Example 15 Preparation Example 4 1.8 g 1.2 g Acetic acid dialysis Example 16 Preparation Example 5 1.8 g 1.2 g Acetone evaporation Example 17 Preparation Example 6 1.8 g 1.2 g Acetone evaporation Example 18 Preparation Example 7, 1.8 g 1.2 g Acetone evaporation Example 19 Preparation Example 8 1.8 g 1.2 g Acetone evaporation Example 20 Preparation Example 9 1.8 g 1.2 g Acetone evaporation

Test Example 1 Measurement of Size by Dynamic Light Scattering of Coenzyme Q10-Containing Polymer Nanoparticles

Zetasizer 3000Hsa manufactured by Malvern, UK was used to measure the average particle size of the nanoparticles prepared in Examples 1-20. The scattering angle was fixed at 90 ° and the temperature was maintained at 25 ° C., and the results are shown in Table 3.

Average diameter (nm) Average diameter (nm) Example 1  56.2 Example 11 284.2 Example 2  64.2 Example 12 296.1 Example 3  53.2 Example 13 276.2 Example 4 212.4 Example 14 249.3 Example 5 271.8 Example 15 198.9 Example 6 278.3 Example 16 295.4 Example 7 223.4 Example 17 286.8 Example 8 256.8 Example 18  72.3 Example 9 201.3 Example 19  53.2 Example 10 243.2 Example 20  48.6

Test Example 2 Antioxidative Effect of Coenzyme Q10-Containing Polymer Nanoparticles on Skin Cells

100 μl of HCES (HEPES-buffered control salt solution) treated by sample concentration was added to dermal dermal fibroblasts, and then the fluorescence of dichlorofluorescein (DCF), which was initially oxidized with ROS (active oxygen species), was measured. It measured by reader (Ex = 485 nm, Em = 530 nm). Thereafter, UVB (30 mJ / cm 2) was irradiated, and the fluorescence immediately after the treatment and after 3 hours of treatment was measured with a fluorescence plate reader (Ex = 485 nm, Em = 530 nm). For comparison, the same test was performed on liposomes containing 1% coenzyme Q10. Table 4 shows the result of comparing the fluorescence after 3 hours of UV irradiation with the control group not treated with%.

Test group Concentration 10 ppm 5 ppm 2.5 ppm 1.25 ppm 0.625 ppm Example 4 62.6 67.6 74.8 79.1 74.9 Liposomes containing 1% coenzyme Q10 87.1 93.8 96.3 89.4 85.5

As can be seen from Table 4, ROS generation inhibitory ability of the coenzyme Q10-containing polymer nanoparticles provided in the present invention is higher than that of coenzyme Q10-containing liposomes.

Test Example 3 Skin Absorption Rate of Coenzyme Q10-Containing Polymer Nanoparticles

After cutting the skin of Hairy cine api and fixing it to a skin absorption test apparatus (Franz-diffusion cell), three kinds of samples were added to the upper part as shown in Table 5, and the lower part was stirred with a buffer solution of appropriate composition. After maintaining 32 ° for 18 hours, the amount of coenzyme Q10 penetrated into the skin was quantified by liquid chromatography. For comparison, the same test was performed on liposomes containing 1% coenzyme Q10.

Total absorption of coenzyme Q10 Area of coenzyme Q10 and absorption per unit time Capric / Caprylic Triglyceride 10% Solution 0 0 Example 4 37.53 μg 2.68 µg / cm 2 · h Liposomes with 1% Coenzyme Q10 23.68 μg 1.69 µg / cm 2 · h

As can be seen from Table 5, the coenzyme Q10-containing polymer nanoparticles provided in the present invention exhibit a skin absorption rate of 159% higher than that of liposomes.

Cosmetics containing coenzyme Q10-containing polymer nanoparticles of the present invention were prepared in the following cream and skin formulations.

<Formulation Examples 1-9> Cream Formulation

The oil-in-water emulsifier type containing the polymer nanoparticles prepared in Example was prepared with the composition shown in Table 6 below.

ingredient My brother's example One 2 3 4 5 6 7 8 9 Lipophilic monostearic acid 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 Glyceryl Stearate 1.5 1.5 1.5 1.5 1.5 1.5 1.5 1.5 1.5 Cetostearyl alcohol 1.5 1.5 1.5 1.5 1.5 1.5 1.5 1.5 1.5 Beeswax 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 Squalane 1.2 1.2 1.2 1.2 1.2 1.2 1.2 1.2 1.2 Polysorbate 60 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 Cetylethylhexanoate 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 Liquid paraffin 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 Methyl paraben 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 Profile paraben 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 Silicone oil 4.0 4.0 4.0 4.0 4.0 4.0 4.0 4.0 4.0 Tocopheryl Acetate 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 Distilled water to 100 to 100 to 100 to 100 to 100 to 100 to 100 to 100 to 100 Urea 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 glycerin 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 Butylene glycol 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 Triethanolamine 0.18 0.18 0.18 0.18 0.18 0.18 0.18 0.18 0.18 Carboxy Vinyl Polymer 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 Example 1 25.0 - - - - - - - - Example 4 - 25.0 - - - - - - - Example 5 - - 25.0 - - - - - - Example 6 - - - 25.0 - - - - - Example 8 - - - - 25.0 - - - - Example 10 - - - - - 25.0 - - - Example 16 - - - - - - 25.0 - - Example 17 - - - - - - - 25.0 - Example 18 - - - - - - - - 25.0

<Formulation Example 10-18> Skin Formulation

Skin formulations containing the polymer nanoparticles prepared in Example were prepared with the compositions shown in Table 7 below.

ingredient Formulation example 10 11 12 13 14 15 16 17 18 Betaine 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 Natto gum 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 Cellulose gum 0.08 0.08 0.08 0.08 0.08 0.08 0.08 0.08 0.08 ethanol 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 Polyoxyethylene Cured Castor Oil 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 Tocopheryl Acetate 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 Polysorbate 60 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 glycerin 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 Example 1 10.0 - - - - - - - - Example 2 - 10.0 - - - - - - - Example 3 - - 10.0 - - - - - - Example 4 - - - 10.0 - - - - - Example 5 - - - - 10.0 - - - - Example 6 - - - - - 10.0 - - - Example 15 - - - - - - 10.0 - - Example 19 - - - - - - - 10.0 - Example 20 - - - - - - - - 10.0 antiseptic a very small amount a very small amount a very small amount a very small amount a very small amount a very small amount a very small amount a very small amount a very small amount Pigment a very small amount a very small amount a very small amount a very small amount a very small amount a very small amount a very small amount a very small amount a very small amount Distilled water to 100 to 100 to 100 to 100 to 100 to 100 to 100 to 100 to 100

Test Example 4 Long-term Storage Stability of Coenzyme Q10 in Formulations

The long-term storage stability of coenzyme Q10 was confirmed for Formulation Example 2 above. Samples were taken at regular intervals while stored in a constant temperature bath at 25 ° C. and 45 ° C. to quantify the content of coenzyme Q10. For effect comparison, a cream formulation containing liposomes containing 1% coenzyme Q10 instead of the polymeric nanoparticles of the Example was prepared with the composition of Table 6 above, and the same test was conducted. The results are shown in Table 8.

Condition 7 days 15th 30 days 45 days Formulation Example 2 25 ℃ 100% 94% 90% 87% 45 ℃ 100% 91% 86% 83% Cream formulations containing liposomes 25 ℃ 100% 93% 88% 82% 45 ℃ 100% 87% 75% 62%

As can be seen from Table 8, the long-term storage stability of coenzyme Q10 in the formulation is better than the state trapped in the polymer nanoparticles of the present invention compared to the state trapped in liposomes. This suggests that by capturing coenzyme Q10 in the polymer nanoparticles of the present invention, it is possible to preserve the titer of coenzyme Q10 in the formulation.

Nanoparticles containing coenzyme Q10 prepared by using the self-associative amphiphilic polymer prepared in the present invention, coenzyme Q10 is a biocompatible and biodegradable polymer containing a high concentration of insoluble coenzyme Q10 component in the water phase As nanoparticles, coenzyme Q10 is more stably collected because it is formed by self-association that does not require a separate mechanical force. Due to the nanoscaled size, the skin absorption rate of coenzyme Q10 is enhanced, and the biocompatibility is excellent for skin. It can be absorbed by the skin and decomposed into the body to release coenzyme Q10 without causing irritation, thereby exhibiting the antioxidant effect of coenzyme Q10 as it is, thereby providing sufficient skin whitening and skin improvement effects.

1 is a transmission electron micrograph of the self-associating polymer nanoparticles containing coenzyme Q10 prepared in Example 1.

Claims (11)

A self-associating polymer nanoparticle having a nano-scale size in which an amphiphilic polymer composed of polycaprolactone as a hydrophobic polymer and a copolymer of polyethylene glycol as a hydrophilic polymer is incorporated. [Formula 1] The self-associating polymer nanoparticles according to claim 1, wherein the nanoparticles have an average particle diameter of 1 to 1,000 nm. The self-associating polymer nanoparticles according to claim 1, wherein the content of coenzyme Q10 collected in the nanoparticles is 0.1 to 50 wt% based on the total weight of the nanoparticles. The self-associating polymer nanoparticles according to claim 1, wherein the amphiphilic polymer is a copolymer having a polycaprolactone and polyethylene glycol in a weight ratio of 1: 9 to 9: 1. The self-associating polymer nanoparticles according to claim 1, wherein the polycaprolactone has a molecular weight of 500 to 100,000 Daltons. The self-associating polymer nanoparticles according to claim 1, wherein the polyethylene glycol has a molecular weight of 500 to 100,000 Daltons. An external preparation composition for skin, comprising the self-associating polymer nanoparticle according to claim 1 as an active ingredient. The composition of claim 7, wherein the composition is softening cream, astringent makeup cream, nourishing cosmetic cream, nutrition cream, massage cream, essence, eye cream, eye essence, cleansing cream, cleansing foam, cleansing water, pack, powder, makeup base, foundation , Body lotion, body cream, body oil, body essence, body cleanser, hair dye, shampoo, rinse, toothpaste, mouthwash, lotion, ointment, gel, cream, patch and spray Skin external preparation composition. Preparing an amphiphilic polymer by copolymerizing polycaprolactone as a hydrophobic polymer and polyethylene glycol as a hydrophilic polymer; Dissolving the prepared amphiphilic polymer and coenzyme Q10 of Formula 1 in an organic solvent and then injecting it in an aqueous solution; And Method of producing a self-associating polymer nanoparticles having a nano-scale size comprising the step of removing the solvent. [Formula 1] 10. The method according to claim 9, wherein the amphiphilic polymer is a block copolymer of polycaprolactone and polyethylene glycol. Self-associating polymer nanoparticles prepared by the method according to claim 9 or 10.