WO2021049742A1 - Cosmetic composition having excellent percutaneous absorption - Google Patents

Abstract

The present invention relates to a cosmetic composition having excellent percutaneous absorption.

Description

Cosmetic composition with excellent transdermal absorption

The present invention relates to a cosmetic composition excellent in transdermal absorption.

The skin is the primary barrier of the human body and functions to protect the internal organs from stimuli caused by external environment such as temperature and humidity changes, ultraviolet rays, and pollutants. The skin is largely composed of three parts: the stratum corneum, the epidermis, and the dermis. The stratum corneum is the outermost layer of the skin, and the skin's barrier function is largely dependent on the physicochemical properties of the stratum corneum.

The stratum corneum consists of several layers of keratinocytes, and keratin, a hydrophobic, insoluble fibrous protein, fills keratin cells, and between keratin cells is a lamella structure filled with intercellular lipids such as ceramide, free fatty acids, and cholesterol. have. Due to the structure of the stratum corneum, physiologically active ingredients, especially water-soluble ingredients, that exhibit efficacy when cosmetics are applied to the skin are difficult to pass through the stratum corneum and be absorbed. Therefore, the cosmetics industry is focusing on the development of technology to increase the transdermal absorption rate of the active ingredient when applying such cosmetics to the skin, as well as the development of functional cosmetics with excellent efficacy such as whitening, wrinkle improvement, antioxidant, and anti-aging.

Percutaneous absorption means that substances penetrated through the skin surface reach and diffuse into the dermis. In order to promote transdermal absorption, a method of adding organic solvents, surfactants, lower fatty acids, etc., known as transdermal absorption accelerators, is known, but the types and contents of organic solvents that can be applied in cosmetics and pharmaceutical external preparations are regulated. In addition, there is a problem in that there are many substances that cause skin irritation among organic solvents, surfactants, and lower fatty acids that have an effect of promoting percutaneous absorption.

On the other hand, a method of using a physiologically active ingredient in a liposome form in a cosmetic composition is known. It is known that liposomes are composed of a lipid bilayer that is structurally similar to intercellular lipids in the cell membrane or stratum corneum, and thus can effectively deliver the physiologically active component inside the liposome into the skin by fusion with the cell membrane. However, not only is an additional process required to form liposomes, but also the efficiency of encapsulating a water-soluble component of liposomes is known to be less than 10%. Accordingly, there is a need for a cosmetic composition capable of increasing transdermal absorption by stabilizing physiologically active ingredients without forming liposomes.

The present invention provides a cosmetic composition excellent in transdermal absorption of the physiologically active component by stabilizing the physiologically active component without forming a liposome.

The present invention provides a cosmetic composition comprising a lysophospholipid, a piperidine-based compound, phloretin, and a physiologically active ingredient.

The cosmetic composition according to the present invention can increase the transdermal absorption rate of the physiologically active component by stabilizing the physiologically active component without forming a liposome. The cosmetic composition can be applied to a variety of cosmetics without restrictions on formulations such as creams, liquids, and emulsions.

1 is a photograph of the appearance of the compositions of Examples 1 and 10.

2 is a graph showing the transdermal permeation amount of a water-soluble bioactive substance.

3 is a graph showing the transdermal permeation amount of an oil-soluble bioactive substance.

Hereinafter, the present invention will be described. However, it is not limited only by the following contents, and each component may be variously modified or selectively used as necessary. Therefore, it should be understood to include all changes, equivalents, and substitutes included in the spirit and scope of the present invention.

The cosmetic composition according to the present invention includes a lysophospholipid, a piperidine-based compound, a phloretin, and a physiologically active ingredient. In addition, if necessary, a thickener, a solvent, a neutralizing agent, and other additives commonly used in the art may be further included. Hereinafter, a detailed look at the composition of the cosmetic composition is as follows.

Skin penetration enhancer

The cosmetic composition of the present invention contains a skin penetration enhancer. The skin penetration accelerator may increase the fluidity of the skin lipid membrane and stabilize the physiologically active ingredients to increase their skin penetration rate. The physiologically active ingredient may be an oil-soluble or water-soluble ingredient. The skin penetration promoter includes lysophospholipid, piperidine-based compound, and phloretin.

Lysophospholipids have a cone-shaped structure to increase the compatibility of skin membranes, thereby increasing the skin transfer rate of physiologically active substances. The lysophospholipid may be used without particular limitation as long as it is commonly used in cosmetic compositions. For example, soybean-derived lysophospholipid, soybean-derived hydrogenated lysophospholipid, egg yolk-derived lysophospholipid, egg yolk-derived hydrogenated lysophospholipid, etc. may be used, and these may be used alone or in combination of two or more. For example, the lysophospholipid may be lysophosphatidylcholine, lysophosphatidylethanolamine, lysophosphatidyl glycerol, lysophosphatidylserine, hydrogenated lysolecithin, and hydrogenated lysophosphatidylcholine.

The lysophospholipid may be contained in an amount of 0.01 to 10% by weight, for example 0.1 to 5% by weight, or 0.5 to 1% by weight, based on the total weight of the cosmetic composition.

Piperidine compounds promote the penetration and penetration of physiologically active substances into the skin barrier. As the piperidine-based compound, piperine, tetrahydropiperine, or a mixture thereof may be used. Piperine is an alkaloid substance that exhibits a spicy taste in pepper, and is known to exhibit anti-inflammatory, central nervous suppression, antidepressant, insecticidal, and anti-obesity effects. Tetrahydropiperine is a naturally derived ingredient obtained from Black Pepper and Long Pepper, and increases the transdermal absorption of physiologically active substances by promoting penetration and penetration of physiologically active substances into the skin barrier in cosmetic compositions.

The piperidine-based compound may be contained in an amount of 0.001 to 10% by weight, for example, 0.01 to 5% by weight, or 0.1 to 1% by weight, based on the total weight of the cosmetic composition.

Phloretin, together with the lysophospholipid and piperidine-based compounds, serves to improve the skin penetration of physiologically active ingredients. In addition, in addition to its role as a skin penetration accelerator, phloletin exhibits effects such as antioxidant and skin tone improvement.

The phloretin may be contained in an amount of 0.001 to 10% by weight, for example, 0.01 to 5% by weight, or 0.1 to 1% by weight, based on the total weight of the cosmetic composition.

The skin penetration promoter is a mixture of lysophospholipid, piperidine-based compound, and phloretin in a weight ratio of 2:1 to 5:1, for example, 2:1:1, 2:3:1 or 2:5:1 Can be. When the blending ratio of the skin penetration accelerator is out of the above-described range, problems such as precipitation may occur due to a decrease in the penetration of the active ingredient or a decrease in the stability of the composition.

For example, the skin penetration promoter may be a combination of lysophospholipid, tetrahydropiperine, and phloretin. The blending ratio of the lysophospholipid, tetrahydropiperine and phloretin may be a weight ratio of 2:1 to 5:1, for example, 2:1:1, 2:3:1 or 2:5:1.

Physiologically active ingredient

The cosmetic composition of the present invention contains a physiologically active ingredient. The bioactive component may be an oil-soluble and/or water-soluble component. The physiologically active ingredient is a material effective for skin health, such as wrinkle improvement and prevention, whitening, antioxidant, and elasticity enhancement, and is not limited as long as it is a material used in the relevant field.

The oil-soluble physiologically active ingredients include, for example, idebenone, tocopherol and its derivatives (such as tocopheryl acetate), coenzyme Q10, oleanolic acid, ursolic acid, diacetyl boldine, and It may be one or more selected from the group consisting of oil-soluble licorice, retinol, and derivatives thereof, but is not limited thereto. For example, the oil-soluble physiologically active ingredient may be idebenone or tocopheryl acetate.

The water-soluble physiologically active ingredients include, for example, hydroquinone derivatives such as arbutin, vitamin C derivatives, niacinamide, adenosine, N-acetylglucosamine, and bisabolol ( Bisabolol), Sangbaekpi extract, may be one or more selected from the group consisting of various water-soluble extracts such as Schisandra chinensis extract, but is not limited thereto. For example, the water-soluble physiologically active component may be niacinamide.

If necessary, the physiologically active ingredient may be included within the range of the usual content used in the field. For example, it may be included in 0.001 to 20% by weight, for example 0.01 to 10% by weight, in another example 0.01 to 5% by weight, and in another example 0.1 to 5% by weight, based on the total weight of the cosmetic composition.

menstruum

The cosmetic composition of the present invention may contain a solvent. The solvent can further improve their transdermal absorption by dissolving physiologically active ingredients. The solvent has a high solubility in water-soluble and/or oil-soluble physiologically active ingredients, and is not particularly limited as long as it is used in the relevant industrial field.

Alcohol, water, or a mixture thereof may be used as the solvent, but is not limited thereto. Monoalcohol, polyol, or a mixture thereof may be used as the alcohol, and as polyol, for example, di(ethylene glycol) ethyl ether, ethoxydiglycol, 1,2-hexanediol, pentylene glycol, dipropylene glycol One or more types selected from can be used. For example, the solvent may be a mixture of di(ethylene glycol) ethyl ether, ethoxydiglycol, 1,2-hexanediol, pentylene glycol, dipropylene glycol, monoalcohol, and water.

If necessary, the solvent may be included within the range of a conventional amount used in the field. For example, it may be included in an amount that satisfies 100% by weight of the total weight of the cosmetic composition, for example, 0.01 to 50% by weight, such as 0.01 to 30% by weight, in another example 0.1 to 15% by weight, based on the total weight of the cosmetic composition, In another example, it may be included in 1 to 10% by weight.

Thickener

The cosmetic composition of the present invention may contain a thickener. As the thickener, a thickener commonly used in the field may be used without limitation. Non-limiting examples of the thickener include carbomer, xanthan gum, acrylate/C10-30 alkyl acrylate crosspolymer, ammonium acryloyl dimethyltaurate/vinylpyrrolidine copolymer, hydroxypropyl starch phosphate, Tapioca starch, gellan gum, hydroxyethylcellulose sodium polyacrylate, polyacrylate crosspolymer-11, and ammonium acryloyldimethyltaurate/behenes-25methacrylate crosspolymer, one or two or more of them are mixed Can be used. For example, the thickener may be carbomer. Carbomer can be increased in a wide pH range and less irritating to the skin.

The thickener may be included within the range of a conventional amount used in the field. For example, it may be contained in an amount of 0.001 to 10% by weight, for example 0.001 to 5% by weight, in another example 0.01 to 5% by weight, and in another example 0.01 to 2.5% by weight, based on the total weight of the cosmetic composition.

corrector

The cosmetic composition of the present invention may contain a neutralizing agent. As the neutralizing agent, those commonly used in the relevant field may be used without limitation. For example, as the neutralizing agent, an amine-based neutralizing agent such as arginine, tromethamine, and triethylamine, water, and mixtures thereof may be used. For example, the neutralizing agent may be a mixture of tromethamine and water.

The neutralizing agent may be included within the range of a conventional amount used in the field. For example, it may be contained in an amount of 0.001 to 10% by weight, for example 0.01 to 5% by weight, based on the total weight of the cosmetic composition.

Other additives

The cosmetic composition of the present invention includes ingredients commonly used in cosmetic compositions, such as fatty substances, organic solvents, solubilizers, thickening agents, gelling agents, softening agents, antioxidants, suspending agents, stabilizers, foaming agents, fragrances, surfactants. , Purified water, ionic or nonionic emulsifiers, fillers, sequestering agents, chelating agents, preservatives, vitamins, blockers, wetting agents, essential oils, dyes, pigments, hydrophilic or lipophilic activators, adjuvants or carriers such as lipid vesicles It may include. The above ingredients may be included in an amount commonly used in the field of cosmetic compositions.

The method for preparing the cosmetic composition of the present invention is not particularly limited, and general methods known in the art may be used without limitation. For example, the cosmetic composition may be prepared by mixing a skin penetration accelerator, a physiologically active ingredient, a thickener, a solvent, a neutralizing agent, and other additives, and emulsifying and cooling the same.

The cosmetic composition can be used in cosmetics of various formulations. For example, softening lotion, astringent lotion, nutritional lotion, functional essence, lotion, nutrition cream, massage cream, basic cosmetics such as eye cream, eye essence, body lotion, body cream, body products such as body oil, pack, cleansing cream, It can be used in cleansing products such as cleansing lotion, cleansing foam, and cleansing water, and color cosmetics such as powder, makeup base, and foundation.

Hereinafter, the present invention will be described in more detail through examples. However, the following examples are only intended to aid understanding of the present invention, and the scope of the present invention is not limited to the examples in any sense.

[Example 1-16]

According to the composition shown in Tables 1 and 2, the cosmetic composition of Examples 1-16 was prepared. In Tables 1 and 2 below, the unit of use of each component is% by weight.

After dispersing the thickener phase in purified water, it was heated to 80° C. to prepare phase A. Phase B was prepared by mixing 1,2-hexanediol, a small amount of purified water, and lysophospholipid in a separate dissolution tank. Dipropylene glycol, ethanol, ethoxydiglycol, piperine, and phloretin were mixed in a separate dissolution tank and then heated to 45° C. to prepare a C phase. After adding phase B and phase C to the A phase, AGI mixing was performed and then cooled to 45 °C. After that, niacinamide and active ingredients were added, followed by AGI mixing. Subsequently, the neutralizing agent was dissolved by heating at 45° C. in a separate dissolution tank, and then added to the previously prepared mixture, followed by AGI mixing. Then, it was cooled to 35°C.

[Comparative Example 1-9]

A cosmetic composition of Comparative Example 1-9 was prepared in the same manner as in Example, except that it was according to the composition of Table 3. In Table 3 below, the unit of use of each component is% by weight.

[Experimental Example 1: Formulation Formation]

Whether or not the formulation of the cosmetic composition of each Example and Comparative Example was formed was observed with the naked eye, and the results (○: the formulation was formed smoothly, △: the surface was awkward) are shown in Table 1-3.

[Experimental Example 2: Stability Evaluation]

Immediately after preparing the composition according to each Example and Comparative Example, the stability was evaluated by observing with the naked eye whether precipitation or precipitation occurred. The evaluation results are shown in Table 1-3. In case of having a transparent property without sediment or precipitation, it was evaluated as ○, in case of a small amount of sediment, precipitation, haze, etc., it was evaluated as △, and in case of occurrence of sediment, precipitation, haze, etc., or having an opaque property, it was evaluated as Х.

1 is a photograph of the appearance of the compositions of Examples 1 and 10. As shown in FIG. 1, the compositions of Examples 1 and 10 showed a transparent appearance immediately after preparation, without precipitation of solids or precipitates.

The cosmetic compositions of Examples 1-4 and 10-16, whose short-term stability was confirmed by the above experiment, were left at room temperature for 3 months and then their appearance was visually observed, and long-term stability was evaluated. The evaluation results are shown in Table 4. In case of having a transparent property without sediment or precipitation, it was evaluated as ○, and in case of occurrence of sediment, precipitation, haze, etc., or having an opaque property, it was evaluated as Х.

[Experimental Example 3: Percutaneous Absorption Analysis]

Percutaneous absorption of the cosmetic compositions of Examples 1-4 and 10-16 under sink conditions using a Franz diffusion cell (effective area: 0.785 cm2, volume of receiving compartment: 5 ml) Was measured.

A chemical membrane (1.5 cm x 1.5 cm) made similar to the degree of absorption of the skin was placed on the receptor chamber, the donor chamber was covered and fixed with a clamp, and the aqueous phase was filled in a Franz diffusion cell. It was maintained at 32±1°C. In Examples 1-4 and 11-16 in which a water-soluble bioactive substance (niacinamide) was used, a phosphate buffered saline (PBS) having a pH of 7.4 was used as the aqueous phase, and an oil-soluble bioactive substance (idebenone ) Was used in Example 10, 50% methanol was used as the aqueous phase.

Subsequently, 0.3 g of each of the cosmetic compositions of each example was uniformly applied to the donor site. After 30 minutes, 1 hour, 2 hours, 4 hours, 6 hours, and 24 hours after application, 5 ml of aqueous phase was collected and analyzed by HPLC.

HPLC analysis conditions

1.Column: Shiseido CAPCELL PAK C18(4.6 ㎜ Х 250 ㎜, 5 ㎛)

2. Detector: RIDetector (differential refractometer)

3. Temp: 35 ℃

3. Flow rate: 1.0 ㎖/min

4. Injection volume: 10 µl

5. Mobile phase: 30% MeOH (for water-soluble physiologically active substances) or 50% MeOH (for soluble physiologically active substances)

6. Wave length: 275 nm

Membrane conditions

2 is a graph showing the transdermal permeation amount of a water-soluble bioactive substance. As shown in FIG. 2, the composition of Examples 1-4 exhibited higher transmittance than the composition of Examples 11-16.

3 is a graph showing the transdermal permeation amount of an oil-soluble bioactive substance. As shown in Figure 3, it was confirmed that the composition of Example 10 continuously permeates the physiologically active substance.

[Experimental Example 4: Preparation of Cream]

A cream containing the cosmetic composition of Example 1 was prepared according to the composition of Table 5 below. In Table 5 below, the unit of use of each component is% by weight.

In addition, a cream containing the cosmetic compositions of Examples 2-4 and 10-16 was prepared in the same manner as above, except that the cosmetic compositions of Examples 2-4 and 10-16 were used, respectively.

[Experimental Example 5: Efficacy Evaluation]

The cream prepared in Experimental Example 4 was evaluated for efficacy. For each group (women in their 20s and 30s, a total of 10 people), after applying the cream of Experimental Example 4 to the facial skin including the eye area for a total of 4 weeks in the morning and evening, the degree of whitening and wrinkle improvement was measured. Evaluation was performed, and the results are shown in Table 6 below. The degree of whitening and wrinkle improvement is evaluated by a 5-point method (very excellent: 5 points, excellent: 4 points, moderate: 3 points, poor: 2 points, very poor: 1 point), and then write the average value of each group score. I did.

The cosmetic composition according to the present invention can increase the transdermal absorption rate of the physiologically active component by stabilizing the physiologically active component without forming a liposome. The cosmetic composition can be applied to a variety of cosmetics without restrictions on formulations such as creams, liquids, and emulsions.

Claims (10)

1. A cosmetic composition comprising a lysophospholipid, a piperidine-based compound, phloretin, and a physiologically active ingredient.
2. The cosmetic composition according to claim 1, wherein the blending ratio of the lysophospholipid, piperidine-based compound, and phloretin is a weight ratio of 2:1 to 5:1.
3. The cosmetic composition according to claim 1, wherein the piperidine-based compound is piperine, tetrahydropiperine, or a mixture thereof.
4. The method of claim 1, comprising 0.01 to 10% by weight of lysophospholipid, 0.001 to 10% by weight of piperidine compounds, 0.001 to 10% by weight of phloretin, and 0.001 to 20% by weight of a physiologically active ingredient, based on the total weight of the cosmetic composition. Cosmetic composition.
5. The cosmetic composition according to claim 1, further comprising at least one of a thickener, a solvent, a neutralizing agent, and other additives.
6. The cosmetic composition according to claim 5, wherein the thickener is contained in an amount of 0.001 to 10% by weight based on the total weight of the cosmetic composition.
7. The cosmetic composition according to claim 5, wherein the solvent is contained in an amount of 0.01 to 50% by weight based on the total weight of the cosmetic composition.
8. The cosmetic composition according to claim 1, wherein the physiologically active ingredient is an oil-soluble or water-soluble ingredient.
9. The cosmetic composition according to claim 1, wherein the physiologically active ingredient is idebenone.
10. The cosmetic composition according to claim 1, wherein the physiologically active ingredient is niacinamide.

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