KR102585227B1 - Composition for stabilizing polyphenolic effective ingredient - Google Patents

Abstract

The present invention relates to a composition for stabilizing poorly soluble polyphenol-based active ingredients, which solves the problem of precipitation of poorly soluble polyphenol-based active ingredients in formulations by using powder and moisturizing ingredients, and at the same time provides a composition with excellent skin safety. It's about.

Description

Composition for stabilizing polyphenolic effective ingredient}

The present invention relates to a composition for stabilizing polyphenol-based active ingredients.

Among the ingredients (hereinafter referred to as efficacy ingredients) that provide skin whitening, wrinkle improvement, or other skin improvement effects, there are many poorly soluble substances that are almost insoluble in either water or oil, such as polyphenols, for example. Therefore, various methods have been attempted to stabilize the effective ingredients in order to use them in high amounts in cosmetics.

In the case of creams or spot cosmetics using an anhydrous formulation that does not contain water, an attempt was made to provide differentiated advantages by stabilizing ingredients that are easily oxidized or precipitated in water and providing heat (Patent Document 1). However, it still had problems such as instability due to aging and a heavy and frustrating feeling in use.

In addition to these formulation technologies, stabilization and efficacy optimization of poorly soluble drugs using polymer micelle or nanoparticle formation technologies using amphiphilic block copolymers (Patent Documents 2 and 3, Non-Patent Document 1), and nanostructured lipid carriers A number of studies have been conducted, such as optimizing the efficacy of polyphenol-based (genistein) active ingredients (Non-Patent Document 2).

However, when manufacturing cosmetic formulations using this method, there is still a problem of precipitation over time, so there is a limit to using poorly soluble ingredients in high amounts.

1. Domestic registered patent 10-0811465 2. Domestic published patent 10-2003-0045611 3. Domestic published patent 2007-0041185

1. Arch pharm Res Vol 30, No. 9, 2007 2. international journal of pharmaceuticals, 453, 2013

The present invention seeks to provide a composition that can stabilize poorly soluble polyphenol-based active ingredients in cosmetic formulations.

In addition, the present invention seeks to provide a cosmetic composition that has an excellent feeling of use and does not cause skin irritation.

In the present invention, a powder containing at least one selected from the group consisting of porous polymer particles and cyclodextrin or a derivative thereof; and

Provides a composition for stabilizing polyphenol-based active ingredients containing a moisturizing ingredient including one or more selected from the group consisting of betaine, alanylglutamine, polyquaternium-51, nicotinamide, urea or its derivatives, and sodium PCA. do.

Additionally, the present invention provides a cosmetic composition containing the composition for stabilizing the polyphenol-based active ingredient described above.

The composition for stabilizing polyphenol-based active ingredients according to the present invention does not irritate the skin, and can be stabilized in cosmetic formulations by improving the solubility of polyphenol-based active ingredients.

The present invention relates to a powder containing at least one selected from the group consisting of porous polymer particles and cyclodextrin or a derivative thereof; and

About a composition for stabilizing polyphenol-based active ingredients containing a moisturizing ingredient containing at least one selected from the group consisting of betaine, alanylglutamine, polyquaternium-51, nicotinamide, urea or its derivatives, and sodium PCA. will be.

Hereinafter, the composition for stabilizing polyphenol-based active ingredients according to the present invention will be described in more detail.

In the present invention, the polyphenol-based active ingredients include genistein, daidzein, frangenidin, polydatin, diosmetin, macelignan, asiaticoside, ginsenoside egg, prickly pear seed extract, glycitein, quercetin, catechin, It may include one or more selected from the group consisting of pheonol, resveratrol, hesperetin, and resperidin. Additionally, the polyphenol-based active ingredient may include a derivative of the polyphenol or an effective ingredient derived from the polyphenol.

The polyphenol-based active ingredient is a poorly soluble ingredient that is almost insoluble in either water or oil. In order to use the polyphenol-based active ingredient in cosmetic compositions, etc., the polyphenol-based active ingredient must be stabilized.

To this end, in the present invention, powder and moisturizing ingredients can be used together to significantly improve the solubility of polyphenol-based active ingredients and stabilize the ingredients within the composition. This stabilization effect is synergistically enhanced compared to when the powder and moisturizing ingredients are used alone, and is expected to be due to not only stabilization by the moisturizing ingredients but also being trapped inside the powder.

In the present invention, powder typically provides a soft texture to the composition, increases absorbency, and prevents shine or stickiness. In the present invention, the powder can be used to prevent precipitation of polyphenol-based poorly soluble active ingredients.

The type of this powder is not particularly limited, and one or more selected from the group consisting of porous polymer particles and cyclodextrin or its derivatives can be used.

In one embodiment, the porous polymer particles include polyurethane derivatives, silica, porous cellulose, polymethylmethacrylate, allyl methacrylates crosspolymer, and polyamide. ) may include one or more selected from the group consisting of

The polyurethane derivatives include, for example, HDI/Trimethylol hexyllactone crosspolymer & Silica, HDI/Trimethylol hexyllactone & silica & dimethicone (HDI/Trimethylol hexyllactone & silica & Dimethicone), and HDI/PPG/Polycaprolactone crosspolymer & silica (HDI/PPG/Polycaprolactone crosspolymer & silica).

In one embodiment, cyclodextrin is a ring-shaped oligosaccharide in which 6 to 12 glucose molecules each have α-1,4 glycosidic bonds, and the cyclodextrin derivative is a cyclic oligosaccharide composed of 7 dextrin molecules substituted with a hydroxypropyl group. Linked hydroxypropyl-β-cyclodextrin can be used.

In an embodiment of the present invention, commercially available plastic powders D-400 and D-800 (Plastic Powder D-400, D-800, Nikko Chemicals Co. Ltd) are used as the powder. The D-400 and D-800 are HDI/trimethylolhexylactone crosspolymer & silica, and the stability of poorly soluble polyphenol-based active ingredients in the composition can be improved by using the above ingredients.

In the present invention, the content of the powder is not particularly limited and may be included at 0.1 to 20% by weight, 0.3 to 10% by weight, 0.5 to 5% by weight, or 1 to 1.5% by weight based on 100% by weight of the composition for stabilizing polyphenol-based active ingredients. You can. Within the above content range, the stability of the polyphenol-based active ingredient can be maintained in the composition. For example, if the powder content is less than 0.1% by weight, it does not affect the stability of the polyphenol-based active ingredient, and if it exceeds 20% by weight, there is a risk of problems with use such as stiffness or sticking.

In the present invention, the moisturizing ingredient serves as a solubilizer for dissolving the polyphenol-based active ingredient, which is a poorly soluble ingredient, and the stability of the composition can be promoted through the moisturizing ingredient.

The type of moisturizing ingredient is not particularly limited, and one or more selected from the group consisting of betaine, alanylglutamine, polyquaternium-51, nicotinamide, urea or its derivatives, and sodium PCA can be used.

In particular, nicotinamide, urea or its derivatives, and sodium PCA have the property of hydrotropy, which is achieved by adding a relatively large amount of a third substance to water insoluble or poorly soluble substances. This refers to the phenomenon of increasing the solubility of . That is, in the present invention, the stability of the composition can be improved by using the above ingredients to increase the solubility of the polyphenol-based active ingredient.

The content of the moisturizing ingredient is not particularly limited, and may be included in an amount of 0.1 to 20% by weight, 0.5 to 15% by weight, or 1.0 to 10% by weight based on 100% by weight of the composition for stabilizing polyphenol-based active ingredients. Within the above content range, the stability of the polyphenol-based active ingredient can be maintained in the composition. For example, if the content of the moisturizing ingredient is less than 0.1% by weight, it does not affect the stability of the polyphenol-based active ingredient, and if it exceeds 20% by weight, there is a risk of problems with the feeling of use and stability of the formulation.

As described above, the present invention provides a composition for stabilizing polyphenol-based active ingredients containing powder and moisturizing ingredients. This composition for stabilizing polyphenol-based active ingredients can be used for purposes such as cosmetics.

In one aspect, the present invention can provide a cosmetic composition containing the composition for stabilizing polyphenol-based active ingredients according to the present invention.

In the present invention, the composition for stabilizing polyphenol-based active ingredients can be added to and used in any cosmetic formulation commonly manufactured in the art, including solutions, suspensions, emulsions, pastes, gels, creams, lotions, powders, soaps, It may be formulated as a surfactant-containing cleansing, oil, powder foundation, emulsion foundation, wax foundation, or spray, but is not limited thereto. More specifically, it can be manufactured into formulations such as lotion, lotion, nutritional cream, massage cream, essence, eye cream, cleansing cream, cleansing foam, cleansing water, pack, spray, or powder.

In the present invention, the composition for stabilizing polyphenol-based active ingredients may be manufactured as a cosmetic composition by adding additives such as moisturizers, oils, sunscreens, fragrances, antioxidants, or pH regulators commonly used in cosmetics. It is not limited.

Hereinafter, to aid understanding of the present invention, it will be described in detail through examples. However, the embodiments according to the present invention may be modified into various other forms, and the scope of the present invention should not be construed as limited to the following embodiments. Embodiments of the present invention are provided to more completely explain the present invention to those skilled in the art.

Example

Examples 1 to 3 and Comparative Examples 1 to 5

A cosmetic composition having the content (weight%, wt%) shown in Table 1 below was prepared.

First, oil phase raw materials 1 to 7, water phase raw materials 8 to 15, and polyol phase raw materials 16 to 18 were each heated and dissolved at 75°C. After that, the polyol phase was added to the water phase and mixed uniformly, and then the oil phase was added to the water phase, emulsified for 5 minutes at 6000 rpm using a homomixer, and then cooled. After that, the fragrance was added at 50 to 55°C, emulsified again at 6000 rpm for 5 minutes using a homomixer, and then cooled to 30°C to prepare the final cosmetic composition.

Raw material name Example 1 Example 2 Example 3 Comparative Example 1 Comparative example 2 Comparative Example 3 Comparative example 4 Comparative Example 5 1. Cetostearyl alcohol 1.5 1.5 1.5 1.5 1.5 1.5 1.5 1.5 2. Glyceryl Stearate/PEG-100 Stearate One One One One One One One One 3. Glyceryl stearate One One One One One One One One 4. Polyglyceryl-3 methylglucose distearade 1.5 1.5 1.5 1.5 1.5 1.5 1.5 1.5 5. Hydrogenated polydecene 4.5 4.5 4.5 4.5 4.5 4.5 4.5 4.5 6. Caprylic/Capric Triglyceride 5 5 5 5 5 5 5 5 7. Dimethicone 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 8. Purified water remaining amount remaining amount remaining amount remaining amount remaining amount remaining amount remaining amount remaining amount 9. Glycerin 5 5 5 5 5 5 5 5 10. EDTA-3Na 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 11. Hexylene glycol 1.5 1.5 1.5 1.5 1.5 1.5 1.5 1.5 12. Betaine - 5 3 - - 8 5 - 13. Nicotinamide 3 - 2 - 8 - 3 - 14.Carbomer(2%) 8 8 8 8 8 8 8 8 15. Tromethamine (10%) 1.5 1.5 1.5 1.5 1.5 1.5 1.5 1.5 16. Dipropylene glycol 10 10 10 10 10 10 10 10 17. Genistein 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 18. Plastic Powder D-400 1.5 1.5 1.5 1.5 - - - - 19. Incense Appropriate amount Appropriate amount Appropriate amount Appropriate amount Appropriate amount Appropriate amount Appropriate amount Appropriate amount

Experimental Example 1: Formulation stability evaluation

Formulation stability evaluation was performed on the cosmetic compositions prepared in Examples and Comparative Examples.

Formulation stability was evaluated by observing stability after storage for 2 months at 0℃, 40℃, 45℃, 50℃ and cycle chamber (-10℃ → 45℃ → -10℃).

The evaluation was indicated as very good: O, trace amount of precipitation: △, and precipitation:

Example 1 Example 2 Example 3 Comparative Example 1 Comparative example 2 Comparative example 3 Comparative Example 4 Comparative Example 5 50℃ O O O O △ △ △ X 45℃ O O O O △ △ △ X 40℃ O O O O △ △ △ X 0℃ O O O △ X X X X Cycle O O O △ X X △ X room temperature O O O △ △ △ △ X

As shown in Table 2, the cosmetic compositions prepared in Examples 1 to 3 were confirmed to be stable without precipitation of genistein compared to the cosmetic compositions prepared in Comparative Examples 1 to 5.

Experimental Example 2: Primary skin irritation test (closed patch experiment)

Skin irritation evaluation was performed on the cosmetic compositions prepared in Examples and Comparative Examples.

After applying a certain amount (0.2g) of each sample to the back area of 50 healthy adult men and women for 24 hours, the pin chamber was removed, and after 4 hours, the change in skin condition was read with the naked eye, and the results are shown in Table 5 below. shown in

The judgment criteria and irritation level were evaluated as follows.

<Judgment criteria>

*-: No erythema or unusual symptoms.

+-: Slightly redder than surrounding area

+: Significantly redder than the surroundings

++: Severe redness and swelling compared to the surrounding area.

Stimulus level = [{(+-) number × 1} + {(+) number × 2} + {(++) number × 3}] / Number of test subjects

sample Number of test subjects Judgment result stimulation ++ + +- - Example 1
Example 2
Example 3
Comparative Example 1
Comparative example 2
Comparative example 3
Comparative example 4
Comparative Example 5 50
50
50
50
50
50
50
50 -
-
-
-
-
-
-
- -
-
-
-
One
-
-
- -
One
One
2
4
2
3
One 50
49
49
48
45
48
47
49 0.00
0.02
0.02
0.04
0.12
0.04
0.06
0.02

As shown in Table 3, although the overall level is acceptable, the cosmetic composition prepared in Comparative Examples tends to have a relatively higher level of irritation than the cosmetic composition prepared in Examples.

Therefore, it can be confirmed that the cosmetic composition according to the present invention (Examples 1 to 3) is safe for the skin.

Claims (7)

Adding a polyol phase containing a polyphenol-based active ingredient and powder to an aqueous phase containing a moisturizing ingredient; and
It includes adding an oil phase,
The powder contains at least one selected from the group consisting of porous polymer particles and cyclodextrin or a derivative thereof,
The moisturizing ingredient includes one or more selected from the group consisting of betaine, alanylglutamine, polyquaternium-51, nicotinamide, urea or its derivatives, and sodium PCA,
A method for producing a composition in which the polyphenol-based active ingredient does not precipitate even when stored for 2 months.
According to claim 1,
The polyphenol-based active ingredients are genistein, daidzein, frangenidin, polydatin, diosmetin, macelignan, asiaticoside, ginsenoside egg, prickly pear seed extract, glycitein, quercetin, catechin, phenol, A method for producing a composition comprising at least one selected from the group consisting of resveratrol, hesperetin, and resperidin.
According to claim 1,
Porous polymer particles are from the group consisting of polyurethane derivatives, silica, porous cellulose, polymethylmethacrylate, allyl methacrylates crosspolymer, and polyamide. A method of preparing a composition comprising one or more selected substances.
According to claim 3,
Polyurethane derivatives include HDI/Trimethylol hexyllactone crosspolymer & Silica, HDI/Trimethylol hexyllactone & silica & Dimethicone, and HDI/Trimethylol hexyllactone & silica & Dimethicone. A method for producing a composition comprising at least one selected from the group consisting of HDI/PPG/Polycaprolactone crosspolymer & silica.
According to claim 1,
A method of producing a composition comprising 0.1 to 20% by weight of powder based on 100% by weight of the composition.
According to claim 1,
A method for producing a composition comprising 0.1 to 20% by weight of the moisturizing ingredient based on 100% by weight of the composition.
A cosmetic composition comprising a composition prepared by the method for producing the composition according to claim 1.