KR102506124B1 - cosmetic composition having excellent stabilizing poorly soluble materials and skin permeability - Google Patents

Abstract

The present invention relates to a cosmetic composition having excellent stabilization performance of poorly soluble substances and skin permeability, wherein the composition according to one aspect may contain the poorly soluble substances in a high content by increasing the solubility of the poorly soluble substances without forming liposomes, and can effectively stabilize the poorly soluble substances in the formulation. In addition, there is an effect that can improve skin improvement effects by increasing the skin delivery power of the poorly soluble substances.

Description

Cosmetic composition having excellent stabilizing poorly soluble materials and skin permeability}

It relates to a cosmetic composition with excellent stabilization performance and skin penetration of poorly soluble substances.

Madecassic acid, asiaticoside, quantitative extract of Centella asiatica including asiatic acid, ceramide, retinoid, coenzyme Q-10, ursolic acid, oleanolic acid, lipoic acid, etc. have excellent skin beauty or improvement effects, As a representative poorly soluble substance, there is a problem that it is difficult to stabilize in a cosmetic composition. In particular, the quantitative extract of Centella asiatica has excellent effects such as skin soothing and wound healing, so its utilization is high. there was.

In order to solve this problem, attempts have been made, such as preparing a formulation in the form of trapping poorly soluble substances in liposomes. However, in the case of stabilizing poorly soluble substances in a formulation through liposome formation, there is a problem in that a large amount of poorly soluble substances cannot be included because the content of poorly soluble substances that can be stabilized is extremely limited.

Korean Patent Publication No. 10-2008-0038812

One aspect is poorly soluble substances; polyols; And to provide a cosmetic composition containing a hydrotrope.

One aspect is poorly soluble substances; polyols; And it provides a cosmetic composition comprising a hydrotrope.

As used herein, the term "poorly soluble substance" means a substance that is not sufficiently soluble in water or oil.

According to one embodiment, the poorly soluble substance is a titrated extract of centella asiatica (TECA), calamine, ceramide, retinol, retinoid, coenzyme Q -10 (coenzyme Q-10), ursolic acid (ursolic acid), oleanolic acid (oleanolic acid) and lipoic acid (lipoic acid) may be any one or more selected from the group consisting of.

The Centella asiatica is also called centella asiatica or tiger herb, and the centella asiatica extract may contain asiaticoside, madecassic acid, and asiatic acid. can The asiaticoside and madecassic acid are involved in the production and secretion of collagen, and thus may have the effect of regenerating damaged skin and increasing the elasticity of the dermis.

The quantitative extract of Centella asiatica may be commercially sold as a raw material for a pharmaceutical composition or a cosmetic composition. It can be prepared by various extraction methods known in the art. For example, the quantitative extract of Centella asiatica can be prepared through a process of contacting with an extraction solvent. Prior to the extraction step, the Centella asiatica may be dried and/or ground. The extraction solvent that can be used to obtain the quantitative extract of Centella asiatica is a solvent that can be generally used in a natural product extraction process, and two or more different solvents may be mixed or used sequentially. The extraction solvent is water, anhydrous or hydrous lower alcohol having 1 to 4 carbon atoms (methanol, ethanol, propanol, butanol), acetone, ethyl acetate, butyl acetate, dichloromethane (CH ₂ Cl ₂ ), chloroform, hexane, And it may be at least one selected from the group consisting of 1,3-butylene glycol. In addition, the quantitative extract of Centella asiatica can be easily prepared by a person skilled in the art according to the drug standards of the Ministry of Food and Drug Safety and known extract preparation methods.

In one embodiment, the poorly soluble material is included in 0.005 to 20% by weight, for example, 0.1 to 20% by weight, 0.1 to 15% by weight, 0.1 to 10% by weight, or 1 to 10% by weight, based on the total weight of the composition. it may be

As used herein, the term "polyol" means an aliphatic compound having two or more hydroxyl groups (-OH).

According to one embodiment, the polyol is present in an amount of 0.0001 to 50% by weight, for example, 0.0001 to 45% by weight, 0.0001 to 40% by weight, 0.0002 to 50% by weight, 0.0002 to 45% by weight, or 0.0002 to 45% by weight, based on the total weight of the composition. It may be included in 40% by weight.

The polyol may include a diol and an aliphatic compound having three or more hydroxyl groups.

The aliphatic compound having three or more hydroxyl groups may include triols, tetrols, and the like, depending on the number of hydroxyl groups. For example, aliphatic compounds having three or more hydroxyl groups include glycerin, sorbitol, diglycerin, erythritol, pentaerythritol, polybutylene glycol-10, polyglycerin-3, polyglycerin-4, polyglycerin-6, polyglycerin Glycerin-10, Polyglycerin-20, Polyglycerin-40, Sorbeth-5, Sorbeth-6, Sorbeth-20, Sorbeth-30, Sorbeth-40, Inositol, Maltitol, Maltose, Mannan, Mannitol, Mannose, lactitol, lactose, dihydroxypropyl PG-glucoside, dithiaoctanediol, fructose, glucamine, methyl glucamine, glucose, methyl glucose-10, methyl glucose-20, ozonezed glycerin, phytantriol, threitol, trimethylolpropane, or xylitol, but is not limited thereto.

According to one embodiment, the polyol may include at least two or more different diols.

The diol is dipropylene glycol, methylpropanediol, 1,3-propanediol, 1,2-hexanediol ), butandiol or 1,3-butylene glycol. Accordingly, the polyol is at least two selected from the group consisting of dipropylene glycol, methylpropanediol, 1,3-propanediol, 1,2-hexanediol, butanediol and 1,3-butylene glycol. It may contain one or more diols.

The methyl propanediol is 0.00005 to 15% by weight, for example, 0.0001 to 10% by weight, 2 to 10% by weight, 3 to 10% by weight, 4 to 10% by weight, 5 to 10% by weight, based on the total weight of the composition, 6 to 10%, 7 to 10%, 8 to 10%, 9 to 10%, 0.0001 to 5%, 0.0001 to 4%, 0.0001 to 3%, 0.0001 to 2%, or 1 to 2% by weight.

The 1,3-propanediol is present in an amount of 0.00005 to 15% by weight, for example, 0.0001 to 10% by weight, 2 to 10% by weight, 3 to 10% by weight, 4 to 10% by weight, 5 to 10% by weight, based on the total weight of the composition. 6 to 10% by weight, 7 to 10% by weight, 8 to 10% by weight, 9 to 10% by weight, 0.0001 to 5% by weight, 0.0001 to 4% by weight, 0.0001 to 3% by weight, 0.0001 to 2% by weight , or may be included in 1 to 2% by weight.

The 1,2-hexanediol is present in an amount of 0.00005 to 15% by weight, for example, 0.0001 to 10% by weight, 2 to 10% by weight, 3 to 10% by weight, 4 to 10% by weight, 5 to 10% by weight, based on the total weight of the composition. 6 to 10% by weight, 7 to 10% by weight, 8 to 10% by weight, 9 to 10% by weight, 0.0001 to 5% by weight, 0.0001 to 4% by weight, 0.0001 to 3% by weight, 0.0001 to 2% by weight , or may be included in 1 to 2% by weight.

The dipropylene glycol is 0.00005 to 35% by weight, for example, 0.0001 to 35% by weight, 1 to 35% by weight, 5 to 35% by weight, 10 to 35% by weight, 0.0001 to 30% by weight based on the total weight of the composition , 1 to 30% by weight, 5 to 30% by weight, 10 to 30% by weight, 15 to 35% by weight, 15 to 30% by weight, 20 to 35% by weight, or 25 to 30% by weight.

The 1,3-butylene glycol is 0.00005 to 35% by weight, for example, 0.0001 to 35% by weight, 1 to 35% by weight, 5 to 35% by weight, 10 to 35% by weight, 0.0001 to 35% by weight, based on the total weight of the composition 30 wt%, 1 to 30 wt%, 5 to 30 wt%, 10 to 30 wt%, 15 to 35 wt%, 15 to 30 wt%, 20 to 35 wt%, or 25 to 30 wt% can

As used herein, the term "hydrotrope" refers to a co-solubilizer that increases the dissolution of poorly soluble substances, and means an agent that solubilizes poorly soluble substances without an organic solvent or surfactant. The hydrotrope has properties similar to surfactants and has the ability to reduce surface tension.

According to one embodiment, the hydrotrope is niacinamide, sodium benzoate, citric acid, a salt of citric acid, urea, sodium 1,3-benzenedi Sulfonate (sodium 1,3-benzenedisulfonate), sodium 4-pyridinecarboxylate, sodium salicylate, sodium benzene sulfonate, caffeine, sodium Sodium p-toluene sulfonate, sodium butyl monoglycolsulfate, 4-aminobenzoic acid, hydrochloric acid (HCl), sodium cumene sulfonate, N ,N-diethylnicotinamide, N-picolylnicotinamide, N-allylnicotinamide, 2-methacryloyloxyethylic phosphorylcholine Phosphorylcholine (2-methacryloyloxyethyl phosphorylcholine), resorcinol, butylurea, pyrogallol, N-picolylacetamide 3.5 (N-picolylacetamide 3.5), procaine HCl , proline HCl, nicotinamide, pyridine, 3-picolylamine, sodium ibuprofen, sodium xylenesulfonate, ethyl carbamate ( ethyl carbamate), pyridoxal hydrochloride, sodium benzoate ( It may be any one or more selected from the group consisting of sodium benzoate, 2-pyrrolidone, and isoniazid.

The hydrotrope is present in an amount of 0.00005 to 30% by weight, for example, 0.0001 to 30% by weight, 0.0001 to 25% by weight, 0.0001 to 20% by weight, 1 to 30% by weight, 1 to 25% by weight, 1 to 30% by weight, based on the total weight of the composition. 20 wt%, 5 to 30 wt%, 5 to 25 wt%, 5 to 20 wt%, 10 to 30 wt%, 10 to 25 wt%, 10 to 20 wt%, 15 to 30 wt%, or 15 to 25 It may be included in weight percent.

The composition may have improved solubility of poorly soluble substances.

The cosmetic composition may be prepared in any formulation commonly prepared in the art to which the present invention pertains. For example, it may be formulated into softening lotion, nutrient lotion, emulsion, lotion, cream, paste, gel, solution, suspension, oil, wax, pack, powder, foundation, spray, surfactant-containing cleansing, etc. It is not limited. More specifically, skin lotion, skin softener, skin toner, nourishing cream, massage cream, milk lotion, powder, essence, eye cream, sun lotion, sun cream, makeup primer, makeup base, BB cream, powder foundation, emulsion foundation , cleansing cream, cleansing foam, cleansing water, soap, pack, stick product, balm type product, spray or powder formulations.

The cosmetic composition may include additional ingredients commonly used in cosmetics, such as thickeners, dispersants, fragrances, fillers, preservatives, preservatives, neutralizers, sweeteners, vitamins, free-radical scavengers, metal ion sequestering agents, functional ingredients and these It may further include any conventional cosmetic ingredient which may be selected from mixtures of One skilled in the art may select any additional ingredients and/or amounts thereof such that the beneficial properties of the compositions according to the present disclosure are not adversely affected or substantially unaffected by the anticipated addition.

In addition, the cosmetic composition may be used by applying alone or overlapping, or by overlapping with other cosmetic compositions other than the present invention. In addition, the cosmetic composition according to the present invention can be used according to a conventional method of use, and the number of times of use can be varied according to the user's skin condition or taste.

The composition according to one aspect has an effect of increasing the solubility of poorly soluble substances without forming liposomes, thereby containing poorly soluble substances in a high content, and effectively stabilizing poorly soluble substances in the formulation. In addition, there is an effect that can improve the skin improvement effect by increasing the skin delivery power of the poorly soluble substance.

It will be described in more detail through the following examples. However, these examples are for illustrative purposes only and the scope of the present invention is not limited to these examples.

Examples 1 to 10 and Comparative Examples 1 to 6. Cosmetic composition preparation

A cosmetic composition was prepared by mixing the ingredients in Tables 1 to 3 below.

More specifically, the cosmetic compositions of Examples 1 to 10 and Comparative Examples 1 to 6 were prepared by mixing each component disclosed in Tables 1 to 3 and stirring with an azimixer for 30 minutes while warming to a temperature of 80 ° C. each was prepared. In Tables 1 to 3 below, the content of each component is shown in weight%.

ingredient Example 1 Example 2 Example 3 Example 4 Example 5 water 25 34.9 82.9 87.8999 92.8999 TECA 10 0.1 0.1 0.1 0.1 niacin amide 25 25 5 0.0001 5 dipropylene glycol 30 30 10 10 0.0001 Methyl Propane Diol 10 10 2 2 2 total 100 100 100 100 100

ingredient Example 6 Example 7 Example 8 Example 9 Example 10 water 84.8999 49.9999 54.9999 34.9999 25 TECA 0.1 10 10 10 One niacin amide 5 0.0001 25 25 5 dipropylene glycol 10 30 0.0001 30 10 Methyl Propane Diol 0.0001 10 10 0.0001 2 total 100 100 100 100 100

ingredient Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 Comparative Example 6 water 87.9 92.9 84.9 50 55 35 TECA 0.1 0.1 0.1 10 10 10 niacin amide - 5 5 - 25 25 dipropylene glycol 10 - 10 30 - 30 Methyl Propane Diol 2 2 - 10 10 - total 100 100 100 100 100 100

Experimental Example 1. Measurement of stability of cosmetic composition and solubility of TECA

In order to confirm the stability of the cosmetic composition, after storing the cosmetic composition prepared in Examples and Comparative Examples for one month at room temperature (25 ℃), it was confirmed whether TECA was precipitated.

In addition, in order to measure the solubility of TECA, 10 mL of each cosmetic composition was put into a 15 mL tube, and centrifuged at 10,000 rpm for 10 minutes to obtain a supernatant. The solubility of TECA in the obtained supernatant was evaluated by HPLC analysis according to Equation 1 below.

[Equation 1]

Solubility (%) = (amount of TECA from supernatant / amount of TECA initially added) X 100 .

In Equation 1, the amount of TECA from the supernatant corresponds to a value obtained by multiplying 1000 by the amount of TECA in 10 μl of injection volume.

Tables 4 and 5 show the precipitation of TECA and the solubility of TECA.

division Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 Example 9 Example 10 stability O O O O O O O O O O Solubility of TECA (%) 100 100 100 92 93 94 96 95 94 100

※ The evaluation criteria for stability are as follows:

O: TECA precipitation does not occur;

X: Precipitation of TECA occurred.

division Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 Comparative Example 6 stability x x x x x x Solubility of TECA (%) 68 55 61 42 35 39

※ The evaluation criteria for stability are as follows:

O: TECA precipitation does not occur;

X: Precipitation of TECA occurred.

As shown in Tables 4 and 5, the compositions of Examples did not cause precipitation of TECA, and it was confirmed that they were stable. On the other hand, it was confirmed that the composition of Comparative Example was unstable due to precipitation of TECA.

In addition, as a result of measuring the solubility of TECA, which is a poorly soluble substance, it was confirmed that the composition of Examples showed a solubility of about 95% or more. On the other hand, in the case of the composition of Comparative Example, by showing a solubility of about 45%, it was confirmed that the composition of Example reduced to half the level. This means that in the case of the composition of the examples, poorly soluble substances can be effectively dissolved.

Experimental Example 2. Skin penetration rate measurement

Using a Franz diffusion cell, the content of TECA penetrating into the skin was measured, and the skin penetration rate (%) of TECA through the composition was calculated by comparing it with the initially introduced TECA content.

More specifically, after preparing the composition of Examples and Comparative Examples as an essence formulation, it was applied to the skin and stored for 12 hours at room temperature (25 ° C.) and humidity of 60%, and then the skin area where the essence was deposited (0.6362 area of cm ² ) was cut with scissors. The cut skin was put into 5 ml of 100% methanol and disrupted for 5 minutes using an ultrasonic disruptor, and then a solution was obtained using a 0.45 μm filter. The content of TECA in the obtained solution was measured using HPLC, and the skin penetration rate of TECA was calculated through Equation 2 below. And, the results are shown in Table 6.

[Equation 2]

Skin penetration rate (%) = (Content of TECA measured in the skin / Content of TECA contained in the deposited essence) X 100

division Example 1 Example 2 Example 3 Example 10 Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 Comparative Example 6 Skin penetration rate (%) 75 66 64 82 21 33 39 12 18 19

As shown in Table 6, in the case of the examples, it was confirmed that the skin penetration rate of TECA, a poorly soluble substance, was excellent.

More specifically, it was confirmed that all of the comparative examples showed a skin penetration rate of less than 40% of TECA. On the other hand, in the case of the examples, it was confirmed that all of them showed a skin penetration rate of TECA of 60% or more. In particular, in the case of Example 10, the skin penetration rate of TECA was 80% or more, showing a significantly increased TECA skin penetration rate compared to the comparative example. Confirmed.

The above results mean that according to the composition of the present invention, poorly soluble substances can be effectively stabilized in the formulation, and skin improvement effects can be improved by increasing the delivery power of poorly soluble substances to the skin.

Claims (8)

poorly soluble substances;
polyols containing at least two or more different diols; and
Contains a hydrotrope,
The diol includes dipropylene glycol and methylpropanediol, and the hydrotrope includes niacinamide, a cosmetic composition. The method of claim 1,
The poorly soluble substance is titrated extract of centella asiatica (TECA), calamine, ceramide, retinol, retinoid, coenzyme Q-10 10), at least one selected from the group consisting of ursolic acid, oleanolic acid, and lipoic acid, a cosmetic composition. The method of claim 1,
The diol is 1,3-propanediol, 1,2-hexanediol or 1,3-butylene glycol Which further comprises a cosmetic composition. The method of claim 1,
The hydrotrope is sodium benzoate, citric acid, a salt of citric acid, urea, sodium 1,3-benzenedisulfonate, sodium 4-pyridinecarboxylate, sodium salicylate, sodium benzene sulfonate, caffeine, sodium p-toluene sulfonate, Sodium butyl monoglycolsulfate, 4-aminobenzoic acid, hydrochloric acid (HCl), sodium cumene sulfonate, N,N-diethylticotinamide (N,N -diethylnicotinamide), N-picolylnicotinamide, N-allylnicotinamide, 2-methacryloyloxyethyl phosphorylcholine phosphorylcholine, resooxy resorcinol, butylurea, pyrogallol, N-picolylacetamide 3.5, procaine HCl, proline HCl, nicotinamide ), pyridine, 3-picolylamine, sodium ibuprofen, sodium xylenesulfonate, ethyl carbamate, pyridoxal hydrochloride , sodium benzoate, 2-pyrrolidine one), and isoniazid (isoniazid) further comprising any one or more selected from the group consisting of, a cosmetic composition. The method of claim 1,
The poorly soluble material is contained in 0.005 to 20% by weight relative to the total weight of the composition, the cosmetic composition. The method of claim 1,
The methylpropanediol is contained in 0.00005 to 15% by weight relative to the total weight of the composition, the cosmetic composition. The method of claim 1,
The dipropylene glycol is contained in 0.00005 to 35% by weight relative to the total weight of the composition, the cosmetic composition. The method of claim 1,
The hydrotrope is a cosmetic composition that is included in 0.00005 to 30% by weight relative to the total weight of the composition.