KR20060028916A - Encapsulated composition for stabilizing epigallocatechin gallate(egcg) in water phase and preparation method thereof - Google Patents

Abstract

The present invention is 0.1 to 25.0% by weight of EGCG (Epigallocatechin gallate); 0.1 to 5.0% by weight of a positive electrode polymer, a negative electrode polymer or a mixture thereof; 0.5-25.0 wt% of a water insoluble polymer, an amphiphilic polymer or a mixture thereof; 0.1-10.0 wt% antioxidant; And it relates to a water-stabilized EGCG capsule composition characterized in that it comprises water, a hydrophilic solvent or a mixture thereof as a residual amount and a method for producing the same, according to the present invention is generated by the external environment such as water, temperature, light It can effectively prevent the instability of EGCG and the instability caused by the chemicals added together when applied to cosmetics, medicines, foods, and the like.

EGCG, Bipolar Polymer, Cathodic Polymer, Water Insoluble Polymer, Complex, Capsule

Description

Water-stabilized EVC capsule composition and preparation method thereof {Encapsulated composition for stabilizing Epigallocatechin gallate (EGCG) in water phase and preparation method

1 is a scanning electron micrograph of an EGCG capsule according to the present invention.

The present invention relates to a water-stabilized EGCG capsule composition and a preparation method thereof, and more particularly, to EGCG by encapsulating and stabilizing EGCG by mixing a water-insoluble polymer with EGCG, a polymer that can interact with it, and an antioxidant in an aqueous phase. Not only can it effectively inhibit degradation by external environment such as water, temperature, light, etc., but also it can maintain the stabilization of EGCG well even when interacting with other substances added together when applied to cosmetics, food, and medicines. The present invention relates to a composition containing EGCG, which is encapsulated and stabilized in an aqueous phase, and a method for preparing the same.

Epigallocatechin gallate ((-) Epigallocatechin gallate (EGCG); hereinafter referred to as 'EGCG') is known to enhance the immune function of the human body and has an excellent antioxidant effect. have. In addition, when applied to the skin promotes the production of collagen (collagen), a component of cartilage, capillaries, muscles, etc., and not only serves to prevent skin damage by destroying chemicals generated by UV rays penetrating the skin, It is known to prevent wrinkles, keep skin healthy, and have an excellent whitening effect. When applied to cosmetic compositions as well as pharmaceutical compositions and daily necessities, it has been expected to exhibit excellent functions.

However, since EGCG has a powerful antioxidant function as a chemical structure of polyphenols, EGCG itself has a problem of being sensitive to air, particularly oxygen, heat, light, and the like, and being easily decomposed by oxidation. The oxidation reaction of EGCG seems to have a mechanism in which the adjacent phenol groups are usually decomposed by oxidizing agents such as radicals and converted to ketone groups to break the ring structure of the phenyl group. In the aqueous solution, about 4% of the total EGCG is dissolved, but since a sufficient amount of EGCG is not stabilized due to rapid oxidation, only a small amount of EGCG can be used as an active ingredient in medicine, food, and cosmetics. Has been reported.

In order to supplement the problems inherent in EGCG and to improve the stability, Korean Patent Publication No. 2003-75492 describes a method of using an EGCG derivative, and in addition, a method of promoting stabilization by lipophilic microcapsules is proposed. However, there is a disadvantage that the stability is made only under very limited conditions. In order to make up for this drawback, the applicant has found a method of stabilizing EGCG in the water phase by utilizing molecular-level interaction, and filed Korean Patent Application No. 2004-17734 on March 16, 2004. This method has a very good stability compared to other methods, but has the disadvantage of being unstable when other polar substances are added to the stabilizing formulation. In other words, when applied to cosmetics, food, pharmaceuticals, other substances other than EGCG is added, and if the added substance interacts very strongly with the bipolar polymer, the negative polymer, and the antioxidant used as a stabilizer, the degree of stabilization Has the disadvantage of decreasing.

 Therefore, the present inventors have conducted research to solve such a conventional problem, and as a result, the EGCG capsule is contained in a water-insoluble capsule material which is insoluble in water, so that the EGCG and the substances added for its stabilization are confined. The present invention has been accomplished by discovering that it can effectively prevent degradation in response to external environments such as heat, air, light, other chemicals, and the like.

It is an object of the present invention to provide a water-stabilized EGCG capsule composition that is encapsulated and capable of effectively stabilizing EGCG in the water phase.

Another object of the present invention is to provide a method for preparing a water-stabilized EGCG capsule composition that is encapsulated and capable of effectively stabilizing EGCG in the water phase.

Still another object of the present invention is to provide a cosmetic composition containing the above water-stabilized EGCG capsule composition as an active ingredient.

Still another object of the present invention is to provide a pharmaceutical composition containing the above-mentioned water-stabilized EGCG capsule composition as an active ingredient.

Still another object of the present invention is to provide a food containing the above-stabilized EGCG capsule composition as an active ingredient.

In order to achieve this object, the water-stabilized EGCG capsule composition according to the present invention comprises 0.1 to 25.0% by weight of EGCG (Epigallocatechin gallate); 0.1 to 5.0% by weight of a positive electrode polymer, a negative electrode polymer or a mixture thereof; 0.5-25.0 wt% of a water insoluble polymer, an amphiphilic polymer or a mixture thereof; 0.1-10.0 wt% antioxidant; And water, a hydrophilic solvent or a mixture thereof as the remainder.

The method for preparing a water-stabilized EGCG capsule composition according to the present invention comprises mixing a hydrophilic solvent, EGCG, anodic polymer, an anionic polymer or a mixture thereof, an antioxidant and a water insoluble polymer, an amphiphilic polymer or a mixture thereof at room temperature. Making; And preparing a capsule by adding water, a hydrophilic solvent or a mixture thereof to the mixture, wherein the EGCG is 0.1 to 25.0% by weight in the composition, and 0.1 to 5.0% by weight of the bipolar polymer, the negative polymer or a mixture thereof. %, The water-insoluble polymer, amphiphilic polymer or a mixture thereof is 0.5 to 25.0% by weight, the antioxidant is 0.1 to 10.0% by weight, characterized in that the mixture of water and hydrophilic solvent is contained as a residual amount.

Another method of preparing a water-stabilized EGCG capsule composition according to the present invention comprises the steps of mixing a hydrophilic solvent, EGCG and a water insoluble polymer, an amphiphilic polymer or a mixture thereof at room temperature; Adding water, a hydrophilic solvent or a mixture thereof to the mixture to dissolve it; And mixing a positive electrode polymer, a negative electrode polymer or a mixture thereof and an antioxidant in the dissolved mixture. 0.1 to 5.0% by weight, 0.5 to 25.0% by weight of the water-insoluble polymer, amphiphilic polymer or a mixture thereof, 0.1 to 10.0% by weight of the antioxidant, characterized in that the mixture of water and hydrophilic solvent is contained as a residual amount .

Hereinafter, first, the water-stabilized EGCG capsule composition of the present invention will be described in detail.

The water-stabilized EGCG capsule composition according to the present invention comprises EGCG, a polymer capable of interacting with EGCG, an antioxidant, a water insoluble polymer, an amphiphilic polymer or a mixture thereof and water, a hydrophilic solvent or a mixture thereof. It is done.

Of these, EGCG (Epigallocatechin gallate) is dissolved in water, hydrophilic solvents or mixtures thereof and becomes anions to react with bipolar polymers to form stable acid-base complexes, or not dissociate in water or hydrophilic solvents. The cationic hydrogen of the phenol reacts with the negative polymer to encapsulate and stabilize the EGCG. At this time, EGCG is preferably contained in an amount of 0.1 to 25.0% by weight based on the total weight of the composition. If it is contained in an amount less than 0.1% by weight, the amount of EGCG that can be stabilized is too small. If it is contained in an amount of more than 25.0% by weight, it is impossible to form a complex with the bipolar polymer and the remaining EGCG becomes excessive and cannot be stabilized. There may be a problem.

Accordingly, the polymer capable of interacting with EGCG may be the above-mentioned bipolar polymer, negative polymer or a mixture thereof, in which "bipolar" is a more broad meaning including "cationic", where the bipolar polymer is in the molecule. Although the kind is not limited as long as it interacts with the polyphenol produced during EGCG dissolution, a molecule having an amine group in its structure, or a structure having a partial cation and capable of stabilizing the anion of the polyphenol is preferable. It should be a molecule that is harmless to the human body. Specific examples thereof include chitosan, lysine, arginine, cystine, polyethyleneimine, cationic copolymer of polyvinylpyrrolidone, polymethyl methacrylate copolymer including quaternary ammonium, styrene copolymer containing quaternary ammonium salt, and the like. have. On the other hand, the negative electrode polymer is not limited as long as it interacts with the cationic hydrogen of the phenol not dissociated in water or hydrophilic solvent, specific examples thereof include polyethylene oxide, polyethylene glycol, polypropylene glycol, polypropylene oxide, Monosaccharides, polysaccharides, cellulose, gelatin, hyaluronic acid, alginic acid, sodium alginate, starch, starch oxide, carboxymethyl cellulose and the like. However, when they are used in a small amount, the complexing effect on the EGCG does not appear, and when the amount is large, the solubility is limited so that precipitates are generated to separate them. Accordingly, it is preferable that the positive electrode polymer, the negative polymer or a mixture thereof is contained in an amount of 0.1 to 5.0% by weight based on the total weight of the composition. In order to stabilize the capsule membrane, the cathode polymer is more preferably used in the same amount as the cathode polymer.

On the other hand, antioxidants are used to further increase the stabilizing effect of some unstabilized EGCG, tyrosine, tryptophan, lipoic acid , vitamin C and its derivatives, vitamin E and its derivatives, vitamin A and its derivatives, sodium sulfite, Sodium disulfite and the like are preferred. However, when an antioxidant is included in excess, it may form a complex directly with the bipolar polymer forming a complex with EGCG, thereby reducing the stability effect. On the other hand, when included in a small amount, there may be a problem in that the stabilizing effect is insufficient. Therefore, the antioxidant is preferably contained in an amount of 0.1 to 10.0% by weight based on the total weight of the composition. More preferably, it is contained in the amount of 0.1-3.0 weight%.

The water insoluble polymer or the amphiphilic polymer may contain any polymer which is insoluble in water. That is, not only a commercially available water-insoluble polymer that can be used to encapsulate the stabilizing composition but also an amphiphilic polymer that is modified to be water-insoluble by reacting with lipophilic portions of the water-soluble polymer. Commercially available water-insoluble polymers include polystyrene, polyacrylic, polyolefin, fluoropolymer, polyacetal, polyamide, polyalkylene, polyalkenylene, polyurethane, polyvinyl acetal, polyvinylbutylal, polycarbonate, polyether , Polyesters, polyester urethane-based polymers, and the like, and the chemical properties thereof are not limited to the above structure as long as they are insoluble in water. As the amphiphilic polymer, synthetic polymers such as ester binders of polyvinyl alcohol, copolymers of polyacrylic acid, ester binders of polyacrylic acid, thioesters of polyacrylic acid, and olefin copolymers of polyvinylpyrrolidone may be used. Ester compound of polylysine, thioester compound of polylysine, ester compound of hyaluronic acid, thioester compound of hyaluronic acid, amide compound of hyaluronic acid, ester compound of cellulose, ester compound of cyclodextrin, amide compound of gelatin, gelatin One or a mixture of two or more selected from the group consisting of an ester compound, an amide compound of chitosan, and a substance for forming liposome can be used. Substances which form liposomes are, for example, dilauuroyl phosphatidyl chlrone, dilauroyl lecithin, dimyristoyl phosphatidyl ethanolamin, dipalmitoyl phosphatidyl glycerol phosphatidyl glycerol, disteroyl phosphatidyl serin, dihexyl dimethylammonium bromide (DiC16 DAB), aerosol OT, monogalactosyl diglyceride, MG galactacyl diglyceride, MG And digalactosyl diglyceride (DGDG). When the content of these compounds is small, the amount of EGCG that can be encapsulated may not be able to be encapsulated efficiently or efficiently, and when the content thereof is high, the viscosity may be too high. Accordingly, the water insoluble polymer, the amphiphilic polymer or a mixture thereof is preferably contained in an amount of 0.5 to 25.0% by weight based on the total weight of the composition.

In addition, water, a hydrophilic solvent, or a mixture thereof, as a substance for dissolving EGCG, occupies the remaining amount except for the EGCG, an ionic polymer, an antioxidant, and a water-insoluble polymer. The hydrophilic solvent may be used as long as it is a polyhydric alcohol without limitation, specifically, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, glycerin, 1,3-butanediol, sorbitol , Tetrahydrofuran and the like can be used. A volatile organic solvent including acetone, ethanol, methanol, etc. may be used together with the polyhydric alcohol, but the solvent does not occupy the composition of the composition because it is volatilized during the preparation of the capsule composition. Dissolution by addition of a hydrophilic solvent can further minimize degradation in the preparation than dissolution of EGCG by water alone. The hydrophilic solvent is most preferably used in an amount of 10 to 30% by weight based on the total weight of the composition, but this is not limitative in the present invention.

Water-stabilized EGCG compositions prepared according to the above compositions also include those solidified by spray drying or lyophilization. In preparing the solidified composition, lactic acid, lactose, and the like may be further added to facilitate drying. The amount is most preferably added in an amount of 5 to 40% by weight based on the total weight of the composition.

According to the present invention, a cosmetic composition, a pharmaceutical composition, a food, etc. containing the water-stabilized EGCG capsule composition as an active ingredient can be prepared. These compositions or foods may be prepared according to conventional manufacturing methods in the art, specifically, pharmaceutical compositions and foods containing the water-stabilized EGCG capsule composition as an active ingredient may be prepared by conventional pharmaceutical or food engineering methods. It can be prepared by adding acceptable conventional excipients and formulating them in the form of conventional formulations by methods of preparing conventional pharmaceutical preparations or by food engineering methods. For example, since the composition of the present invention is harmless to the human body, it may be formulated in the form of gel, membrane, bead, mesh, or coated fiber, and may be variously applied to injections, external skin preparations, and the like. In addition, when the composition is coated and dried on a gauze nonwoven substrate, it may provide an effect such as a whitening effect or exfoliation as a cosmetic material. The EGCG composition of the present invention may be contained in a conventional cosmetic composition in an amount of 1.0 × 10 ⁻⁴ to 1.0 × 10 ¹ wt% in the total composition as an active ingredient. In addition, the coating on the fiber is in the form of a gauze, when attached to the wound has the effect of increasing the speed of wound recovery.

Hereinafter, the method of preparing the above water-stabilized EGCG capsule composition will be described in more detail.

As a first method, the water-stabilized EGCG capsule composition according to the present invention comprises a hydrophilic solvent, EGCG, an anodic polymer, an anionic polymer or a mixture thereof, an antioxidant and a water insoluble polymer, an amphiphilic polymer or a mixture thereof at room temperature. Mixing; And preparing a capsule by adding water, a hydrophilic solvent or a mixture thereof to the mixture, wherein the EGCG is 0.1 to 25.0% by weight in the composition, and 0.1 to 5.0% by weight of the bipolar polymer, the negative polymer or a mixture thereof. %, The water-insoluble polymer, amphiphilic polymer or a mixture thereof is 0.5 to 25.0% by weight, the antioxidant is 0.1 to 10.0% by weight, characterized in that the mixture of water and hydrophilic solvent is contained as a residual amount.

In the mixing step, all of the additives may be added and mixed at the same time as described above, but may be sequentially added and mixed. That is, dissolving EGCG in a hydrophilic solvent to prepare an aqueous EGCG solution; Mixing a positive electrode polymer, a negative electrode polymer or a mixture thereof in the EGCG aqueous solution; Adding and adding the antioxidant to the ionic polymer mixture; Preparing a water-insoluble polymer aqueous solution by dissolving a water-insoluble polymer, an amphiphilic polymer or a mixture thereof in a hydrophilic solvent; And mixing the antioxidant addition mixture with the water-insoluble polymer aqueous solution.

After the capsule manufacturing is completed may further comprise the step of adding an antioxidant to water.

As a second method, the water-stabilized EGCG capsule composition according to the present invention comprises the steps of mixing a hydrophilic solvent, EGCG and a water insoluble polymer, an amphiphilic polymer or a mixture thereof at room temperature; Adding water, a hydrophilic solvent or a mixture thereof to the mixture to dissolve it; And mixing the bipolar polymer, the negative polymer, or a mixture thereof and an antioxidant in the dissolved mixture.

In the above two methods, when EGCG is simply dissolved in water, it can be decomposed by water before EGCG is stabilized. Therefore, dissolution in preparation can be minimized by dissolving in water first and then dissolving in water. Is preferably left in an amount of 10 to 30% by weight based on the total weight of the composition.

In the two methods, the EGCG in the composition is 0.1 to 25.0 wt%, the bipolar polymer, the negative polymer or a mixture thereof is 0.1 to 5.0 wt%, the water insoluble polymer, amphiphilic polymer or a mixture thereof is 0.5 to 25.0 By weight, the antioxidant is 0.1 to 10.0% by weight, the mixture of water and a hydrophilic solvent is contained as the balance. As the hydrophilic solvent, a mixture of a polyhydric alcohol or a volatile organic solvent and a polyhydric alcohol may be used, but after the capsule manufacturing step, all of the volatile organic solvent is removed or removed so that only the polyhydric alcohol remains as a hydrophilic solvent to form a composition of the capsule composition. Done.

The water-stabilized EGCG composition of the present invention prepared by this preparation method is based on the fact that EGCG is dissolved to become an anion, and the stable acid-base complexes with cationic substances such as EGCG, chitosan and amino acids in the composition Some oxidative reactions occur after EGCG is first stabilized by the interaction of anionic polymers such as polyethylene oxide, polyethyleneglycol and the like with cationic hydrogens of phenols that do not form or dissociate in water or hydrophilic solvents By further stabilizing the mixture, the water-insoluble polymer, the amphiphilic polymer, or a mixture thereof is mixed with a complex of water-soluble EGCG to form a matrix, and the complex of the EGCG is dispersed in the water-insoluble polymer matrix. The mixture of water-insoluble polymer and EGCG complex When dispersed in water, the water-insoluble polymer that forms the matrix precipitates, and the matrix that precipitates encapsulates while encapsulating the dispersed phase, which causes EGCG to be decomposed by external environment such as water, oxygen, temperature, and light. Not only can it be effectively prevented to maintain stability, but also to maintain stability under interaction with other substances that can be added together when applied to cosmetics, foods and pharmaceuticals.

Particularly, in the case of encapsulating EGCG in a water-insoluble polymer and dispersing it in an aqueous phase containing a stabilizer of EGCG, the stabilized capsule of EGCG thus prepared is encapsulated by a water-insoluble polymer in a solid phase, and thus oxygen, water In this case, the EGCG contained in the solid phase can be stabilized in the water phase if it is eluted in water.

Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited thereto.

<Examples 1-18 and Comparative Examples 1-2>

Furtherance Example Comparative example One 2 3 4 5 6 7 8 9 One 2 10 11 12 13 14 15 16 17 18   Hydrophilic Solvent glycerin 10 - - - - - - - - - - Diethylene glycol - 10 - 10 10 30 30 30 30 30 30 Dipropylene glycol - - 10 - - - - - - - - ethanol - - - 20 20 - - - - - - Acetone 50 50 50 30 30 30 30 30 30 - - Methanol - - - - - 20 20 20 20 - -   Polar polymer Sugar One 3 - - - - - - - - One Starch - - One 3 - - - - - - - Polyethylene oxide - - - - One 3 - - - - - Chitosan One - - - - - 0.2 - - - - gelatin - - - - 0.5 - - 0.2 - - - Hyaluronic acid - - One - - - - - 0.2 - -   Antioxidant Tyrosine 2 - - - - - - - - - - Lipoic acid - 0.5 - - - - - - - - - Vitamin A - - One - - - - - - - - Vitamin c - - - 2 - - One One One - - Vitamin E - - - - 2 - - - - - - Sodium disulfite - - - - - One - - - - One EGCG 5 20 15 5 10 15 5 10 15 5 10

  Water Insoluble Polymer Polyester 10 20 - - - - - - - - - polystyrene - - 8 15 - - - - - - - Hyaluronic acid copolymer - - - - 20 15 - - - - - Chitosan copolymer - - - - - - 10 5 - - - Polyvinylpyrrolidone Copolymer - - - - - - - - 15 - - water 71 46.5 64 65 56.5 36 53.8 53.8 38.8 65 58

-Manufacturing Method-

1) First, a single or mixture of hydrophilic solvents was added to the flask, and then EGCG was added and dissolved according to the composition of Table 1 above.

2) At room temperature, the polar polymer and antioxidant were sequentially added to the solution of 1) according to the composition of Table 1 and dissolved.

3) The water insoluble polymer was dissolved in a soluble amount of hydrophilic solvent. If necessary, the dissolution step of the water-insoluble polymer may be achieved by raising the temperature. After melting, lower the temperature to room temperature again.

4) The solution of 2) and the water insoluble polymer aqueous solution of 3) were mixed.

5) Capsules were prepared by mixing the solution of 4) in a mixture of water and hydrophilic solvent with slow stirring.

6) When the capsule was prepared, the solvents which were volatilized at a low pressure of about 100 mHg and a temperature of 60 ° C. were removed. Acetone, ethanol and methanol were easily removed from the organic solvent used in the above examples.

1 is a photograph taken using a scanning electron microscope of the capsule composition of Example 1 prepared according to the above manufacturing method, it can be seen that the composition of the present invention is prepared in the form of a capsule.

Experimental Example 1 Measurement of titer of EGCG

The initial titer of EGCG in the composition of the said Examples 1-9 and Comparative Examples 1-2 was set to 100, The titer of EGCG after 1 month was measured at room temperature, 37 degreeC, and 45 degreeC, The result is shown in Table 2. Indicated. The measurement was performed using Hewlett-Packard's HP 1090 HPLC system, the detector was DAD 280nm, the column was Agilent XDB C-18. Before the measurement, the sample was first used to disintegrate the water-insoluble capsule material with acetone and to dilute about 100 times with acetonitrile.

Example Comparative example One 2 3 4 5 6 7 8 9 One 2 Room temperature 100 99 100 100 100 99 99 99 98 75 95 37 ℃ 100 99 99 98 99 99 99 97 97 65 92 45 ℃ 99 98 99 97 99 98 97 97 95 57 87

As can be seen from Table 2, the titer of the composition of Comparative Example 1, in which the antioxidant and the polar polymer were not added, and the composition of Comparative Example 2, in which the polar polymer and the antioxidant were added but not encapsulated because the water-insoluble polymer was not added, were high temperature. Not only at but also at room temperature was significantly lower compared to the examples. Thus, it can be seen that the EGCG stabilization efficacy of the composition of the example is much better.

<Examples 10-18>

The composition of Examples 10 to 18 was prepared by only changing the preparation method under the composition of Table 1. At this time, the composition of Examples 10-18 follows the composition of Examples 1-9 sequentially.

-Manufacturing Method-

1) First, a single or mixture of hydrophilic solvents was added to the flask, and then EGCG was added and dissolved according to the composition of Table 1 above.

2) The water-insoluble polymer was dissolved in a soluble amount of a hydrophilic solvent at room temperature. If necessary, the dissolution step of the water-insoluble polymer may be achieved by raising the temperature. After melting, lower the temperature to room temperature again.

3) The solution of 1) and the water-insoluble polymer aqueous solution of 2) were mixed.

4) The capsule of 3) was mixed with a mixture of water and a hydrophilic solvent with slow stirring to prepare a capsule.

5) Once the capsule is prepared, remove the solvents which volatilize at a low pressure of about 100 mHg, a temperature of 60 ℃. Acetone, ethanol and methanol were easily removed from the organic solvent used in the above examples.

6) The antioxidant and polar polymer were added according to the composition of Table 1 and dissolved in the water phase.

Experimental Example 2 Titer Measurement of EGCG

The initial titer of EGCG in the composition of the said Examples 10-18 was set to 100, The titer of EGCG after 1 month was measured at room temperature, 37 degreeC, and 45 degreeC, The result is shown in Table 3. The measurement was performed using Hewlett-Packard's HP 1090 HPLC system, the detector was DAD 280nm, the column was Agilent XDB C-18. Before the measurement, the sample was first used to disintegrate the water-insoluble capsule material with acetone and to dilute about 100 times with acetonitrile.

Example 10 11 12 13 14 15 16 17 18 Room temperature 100 99 100 100 100 99 99 99 100 37 ℃ 99 99 100 99 99 98 97 96 95 45 ℃ 98 98 99 98 97 97 96 95 91

As can be seen from Table 3, even when EGCG is encapsulated first, and a polar polymer and an antioxidant are added to the water phase, it can be seen that it shows very excellent stability as in Examples 1-9. From this, it can be seen that the EGCG capsule compositions prepared by two different methods are all stabilized with respect to the external environment.

As can be seen from the above, according to the present invention, not only can EGCG be effectively inhibited from being decomposed by external environment such as water, temperature, light, etc., but also with other substances present when applied to cosmetics, food, and pharmaceuticals. Since it can be stabilized even under the interaction of, it can be usefully used in cosmetic compositions, pharmaceutical compositions, food, household goods, etc., because it is an aqueous phase, it is possible to prepare a water-stabilized EGCG capsule composition, which is a nanoparticle assembly with excellent feeling.

Claims (17)

0.1-25.0 weight% of EGCG (Epigallocatechin gallate); 0.1 to 5.0% by weight of a positive electrode polymer, a negative electrode polymer or a mixture thereof; 0.5-25.0 wt% of a water insoluble polymer, an amphiphilic polymer or a mixture thereof; 0.1-10.0 wt% antioxidant; And Water, hydrophilic solvent or mixtures thereof Water-stabilized EGCG capsule composition comprising a. The water-stabilized EGCG capsule composition of claim 1, wherein the hydrophilic solvent is contained in an amount of 10-30% by weight. The water-stabilized EGCG capsule composition of claim 1 or 2, wherein the EGCG composition is solidified by spray drying or lyophilization. The method of claim 1 or 2, wherein the bipolar polymer is chitosan, lysine, arginine, cystine, polyethyleneimine, polyvinylpyrrolidone cationic copolymer, polymethyl methacrylate copolymer including quaternary ammonium and quaternary ammonium salt It is one or a mixture of two or more selected from the group consisting of styrene copolymers comprising, the negative polymer is polyethylene oxide, polyethylene glycol, polypropylene glycol, polypropylene oxide, monosaccharides, polysaccharides, cellulose, gelatin, hyaluronic acid, A water-stabilized EGCG capsule composition, characterized in that one or two or more mixtures selected from the group consisting of alginic acid, sodium alginate, starch, starch oxide and carboxymethylcellulose. The method of claim 1 or 2, wherein the water-insoluble polymer is polystyrene-based, polyacrylic-based, polyolefin-based, fluoropolymer, polyacetal, polyamide, polyalkylene, polyalkenylene, polyurethane, polyvinyl acetal, polyvinylbutyl It is one, or a mixture of two or more selected from the group consisting of eggs, polycarbonates, polyethers, polyesters and polyester urethane-based polymers, the amphiphilic polymer is an ester combination of polyvinyl alcohol, a copolymer of polyacrylic acid, polyacrylic acid Of ester bonds, thioesters of polyacrylic acid, olefin copolymers of polyvinylpyrrolidone, ester compounds of polylysine, thioester compounds of polylysine, ester compounds of hyaluronic acid, thioester compounds of hyaluronic acid, hyaluronic acid Amide compounds, ester compounds of cellulose, cyclo Ester compound of the host Lin, amide compounds of gelatin, ester compounds, amide compounds, and the group consisting of the material forming the liposomes alone or in combination of two or more thereof selected from chitosan of the gelatin may, characterized in that-stabilized EGCG capsule composition. According to claim 1 or 2, wherein the antioxidant is selected from the group consisting of tyrosine, tryptophan, lipoic acid, vitamin C and its derivatives, vitamin E and its derivatives, vitamin A and its derivatives, sodium sulfite, sodium disulfite A water-stabilized EGCG capsule composition, characterized in that the species or a mixture of two or more species. The water-stabilized EGCG capsule composition of claim 1 or 2, wherein the hydrophilic solvent is a polyhydric alcohol. The method of claim 7, wherein the polyhydric alcohol is one or two selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, glycerin, 1,3-butanediol, sorbitol and tetrahydrofuran A water-stabilized EGCG capsule composition, characterized in that it is a mixture of two or more species. Hydrophilic solvents at room temperature; EGCG; Bipolar polymers, negative polymers or mixtures thereof; Antioxidants; And mixing the water insoluble polymer, the amphiphilic polymer or a mixture thereof; And To prepare a capsule by adding water, a hydrophilic solvent or a mixture thereof to the mixture, 0.1 to 25.0 wt% of the EGCG in the composition, 0.1 to 5.0 wt% of the bipolar polymer, negative polymer or a mixture thereof, 0.5 to 25.0 wt% of the water-insoluble polymer, amphiphilic polymer or a mixture thereof, the antioxidant The agent is 0.1 to 10.0% by weight, and a mixture of water and a hydrophilic solvent is contained as a residual amount, the method of producing a water-stabilized EGCG capsule composition. The method of claim 9, wherein the mixing step comprises the steps of dissolving EGCG in a hydrophilic solvent to prepare an aqueous solution of EGCG; Mixing a positive electrode polymer, a negative electrode polymer or a mixture thereof in the EGCG aqueous solution; Adding and adding the antioxidant to the ionic polymer mixture; Preparing a water-insoluble polymer aqueous solution by dissolving a water-insoluble polymer, an amphiphilic polymer or a mixture thereof in a hydrophilic solvent; And mixing the antioxidant addition mixture with the aqueous solution of water insoluble polymer. 10. The method of claim 9, wherein the step of preparing the capsules comprises dissolving the EGCG mixture in a hydrophilic solvent and then dissolving in water, wherein the hydrophilic solvent remains in an amount of 10 to 30% by weight. Method for preparing a stabilized EGCG capsule composition. The method of claim 9 or 10, The bipolar polymer is a group consisting of chitosan, lysine, arginine, cystine, polyethyleneimine, polyvinylpyrrolidone cationic copolymer, polymethyl methacrylate copolymer including quaternary ammonium and styrene copolymer containing quaternary ammonium salts. It is one or a mixture of two or more selected from the above, the negative polymer is polyethylene oxide, polyethylene glycol, polypropylene glycol, polypropylene oxide, monosaccharides, polysaccharides, cellulose, gelatin, hyaluronic acid, alginic acid, sodium alginate, starch, starch oxide And carboxymethyl cellulose, or a mixture of one or two or more selected from the group consisting of polystyrene, polyacrylic, polyolefin, fluoropolymer, polyacetal, polyamide, polyalkylene, polyalkenylene, poly Urethane, Polyvinyl Acetal, Polyvinyl Butyl Al, Poly Carbonate, polyether, polyester, and one or more mixtures of two or more selected from the group consisting of polyester urethane-based polymers, wherein the amphiphilic polymer is an ester combination of polyvinyl alcohol, a copolymer of polyacrylic acid, an ester of polyacrylic acid Binder, thioester of polyacrylic acid, olefin copolymer of polyvinylpyrrolidone, ester compound of polylysine, thioester compound of polylysine, ester compound of hyaluronic acid, thioester compound of hyaluronic acid, amide compound of hyaluronic acid , An ester compound of cellulose, an ester compound of cyclodextrin, an amide compound of gelatin, an ester compound of gelatin, an amide compound of chitosan, and a mixture of substances forming liposomes. Is one or a mixture of two or more selected from the group consisting of tyrosine, tryptophan, lipoic acid, vitamin C and its derivatives, vitamin E and its derivatives, vitamin A and its derivatives, sodium sulfite and sodium disulfite, A solvent is a method of preparing a water-stabilized EGCG capsule composition, characterized in that a polyhydric alcohol or a mixture of a volatile organic solvent and a polyhydric alcohol. The method of claim 12, wherein the hydrophilic solvent is a mixture of a volatile organic solvent and a polyhydric alcohol, and the volatile organic solvent is removed after the capsule manufacturing step. Mixing a hydrophilic solvent, EGCG and a water insoluble polymer, an amphiphilic polymer or a mixture thereof at room temperature; Adding water, a hydrophilic solvent or a mixture thereof to the mixture to dissolve it; And Comprising the step of mixing the bipolar polymer, the negative polymer or a mixture thereof and the antioxidant to the dissolved mixture, 0.1 to 25.0 wt% of the EGCG in the composition, 0.1 to 5.0 wt% of the bipolar polymer, negative polymer or a mixture thereof, 0.5 to 25.0 wt% of the water-insoluble polymer, amphiphilic polymer or a mixture thereof, the antioxidant The agent is 0.1 to 10.0% by weight, and a mixture of water and a hydrophilic solvent is contained as a residual amount, the method of producing a water-stabilized EGCG capsule composition. Cosmetic composition containing the water-stabilized EGCG capsule composition of claim 1 as an active ingredient.  A pharmaceutical composition comprising the water-stabilized EGCG capsule composition of claim 1 as an active ingredient.  A food comprising the water-stabilized EGCG capsule composition of claim 1 as an active ingredient.

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