KR102066108B1 - Cosmetic compositions containing two kinds of compounds comprising phenyl rings - Google Patents

Abstract

The present invention relates to a cosmetic composition comprising two compounds having a phenyl ring in a specific ratio.

Description

Cosmetic composition containing two kinds of compounds which have phenyl ring {COSMETIC COMPOSITIONS CONTAINING TWO KINDS OF COMPOUNDS COMPRISING PHENYL RINGS}

The present invention relates to a cosmetic composition comprising two compounds having a phenyl ring in a specific ratio.

In general, in order to prepare a functional cosmetic formulation using a crystalline material, it is common to use a microcapsules made of a polymer or a high HLB surfactant to inhibit the crystallinity of the drug and dissolve it in a form that is easily absorbed by the skin. However, the microcapsules using polymers determine the solubility of the drug in the capsule depending on the compatibility with the polymer and the crystallinity of the polymer wall itself. Because of this, the bioavailability is greatly reduced. On the other hand, the surfactant has to use a certain concentration or more of the surfactant in order to efficiently dissolve the crystalline material, there is a disadvantage that can cause skin irritation. In addition, since the surfactant inhibits crystal formation in a dynamic equilibrium state, crystal growth occurs rapidly according to the surrounding environment, thereby lowering the bioavailability of the drug.

Accordingly, there is a need in the art for a method for increasing skin absorption by reducing melting time and increasing solubility between two or more materials having high crystallinity.

Republic of Korea Patent No. 10-1141929

An object of the present invention is to improve the skin absorption rate by dissolving two or more substances having strong crystallinity.

In order to achieve the above object, the present invention provides a cosmetic composition comprising a polar oil and two compounds having a phenyl ring.

The present invention also provides a method for enhancing the skin absorption rate of a cosmetic composition comprising mixing a polar oil with two compounds having a phenyl ring.

According to the cosmetic composition of the present invention, it is useful because it lowers the melting point, that is, the melting point between materials with strong crystallinity, and thus, the melting time is also reduced, and thus the solubility and the skin absorption rate can be improved. In addition, this effect is possible without the use of surfactants harmful to the human body, so the skin irritation is also very small.

1 is 5-methyl-2- (methylethyl) phenyl (2E) -3- (3,4,5-trimethoxyphenyl) prop-2-enoate (5-methyl-2- ( methylethyl) phenyl (2E) -3- (3,4,5-trimethoxyphenyl) prop-2-enoate) and 2-((3E) -4 (2H, 3H-benzo [3, 4-d] 1, 3- Dioxolan-5-yl) -2-oxo-but-3-enyloxy) -5-hydroxy-4H-pyran-4-one) (2-((3E) -4 (2H, 3H-benzo [3 , 4-d] 1, 3-dioxolan-5-yl) -2-oxo-but-3-enyloxy) -5-hydroxy-4H-pyran-4-one)), and the melting point I will look at.
2 is 5-methyl-2- (methylethyl) phenyl (2E) -3- (3,4,5-trimethoxyphenyl) prop-2-enoate (5-methyl-2- (methylethyl) phenyl (2E) -3- (3,4,5-trimethoxyphenyl) prop-2-enoate) and 2-((3E) -4 (2H, 3H-benzo [3, 4-d] 1, 3-dioxolane -5-yl) -2-oxo-but-3-enyloxy) -5-hydroxy-4H-pyran-4-one) (2-((3E) -4 (2H, 3H-benzo [3, 4] -d] 1, 3-dioxolan-5-yl) -2-oxo-but-3-enyloxy) -5-hydroxy-4H-pyran-4-one)) in a specific ratio, and in each case Compared to the faster dissolution rate.
Figure 3 is taken with a TEM image of the composition and the control of the present invention.
Figure 4 observes the skin absorption rate seen between the composition of the present invention and the control.

The present invention, in one aspect, relates to a cosmetic composition comprising a polar oil and two compounds having a phenyl ring group.

As used herein, the term "phenyl ring" refers to an aromatic ring group including a hydroxy group. Thus, a phenyl ring may be used to prepare a eutectic mixture by allowing a pi-pi reaction between compounds having a phenyl ring. . Specifically, the compound having a phenyl ring group is 5-methyl-2- (methylethyl) phenyl (2E) -3- (3,4,5-trimethoxyphenyl) prop-2-enoate (5-methyl 2- (methylethyl) phenyl (2E) -3- (3,4,5-trimethoxyphenyl) prop-2-enoate) and 2-((3E) -4 (2H, 3H-benzo [3, 4-d] 1,3-dioxolan-5-yl) -2-oxo-but-3-enyloxy) -5-hydroxy-4H-pyran-4-one) (2-((3E) -4 (2H, 3H -benzo [3, 4-d] 1, 3-dioxolan-5-yl) -2-oxo-but-3-enyloxy) -5-hydroxy-4H-pyran-4-one)), It is not limited to this.

Specifically, the present invention utilizes eutectic produced when two drugs having a high melting point (ie, melting point) are mixed at a specific ratio, thereby lowering the melting point of the crystalline active material to prepare an emulsion more easily. Through this, a cosmetic composition having a high skin delivery rate can be prepared.

5-methyl-2- (methylethyl) phenyl (2E) -3- (3,4,5-trimethoxyphenyl) prop-2-enoate (5-methyl-2- (methylethyl) phenyl ( 2E) -3- (3,4,5-trimethoxyphenyl) prop-2-enoate) compound is generally referred to as a melasolv brand name, and has a structure as shown in Chemical Formula 1 below. In addition, the above

2-((3E) -4 (2H, 3H-benzo [3, 4-d] 1, 3-dioxolan-5-yl) -2-oxo-but-3-enyloxy) -5-hydroxy- 4H-pyran-4-one) (2-((3E) -4 (2H, 3H-benzo [3, 4-d] 1, 3-dioxolan-5-yl) -2-oxo-but-3-enyloxy ) -5-hydroxy-4H-pyran-4-one)) compound is also referred to as the brand name serenoidoid G (seletinoid G), and has the structure shown in formula (2) below.

R is H, ME, Et, Pr or Bu, and X is CO or CH ₂ = CH ₂ CO.

In the present specification, the "polar oil" may mean an oil having polarity. Specifically, it may include an ester oil and a phenyl-based oil, but is not limited thereto.

In the cosmetic composition of one aspect of the present invention, the two compounds having the phenyl ring are 5-methyl-2- (methylethyl) phenyl (2E) -3- (3, 4, 5-trimethoxyphenyl) Prop-2-enoate (5-methyl-2- (methylethyl) phenyl (2E) -3- (3,4,5-trimethoxyphenyl) prop-2-enoate) and 2-((3E) -4 ( 2H, 3H-benzo [3, 4-d] 1, 3-dioxolan-5-yl) -2-oxo-but-3-enyloxy) -5-hydroxy-4H-pyran-4-one) ( 2-((3E) -4 (2H, 3H-benzo [3, 4-d] 1, 3-dioxolan-5-yl) -2-oxo-but-3-enyloxy) -5-hydroxy-4H-pyran -4-one)).

In the cosmetic composition which is an aspect of the present invention, the 2-((3E) -4 (2H, 3H-benzo [3, 4-d] 1, 3-dioxolan-5-yl) -2-oxo-butyrate 3-enyloxy) -5-hydroxy-4H-pyran-4-one) (2-((3E) -4 (2H, 3H-benzo [3, 4-d] 1, 3-dioxolan-5- yl) -2-oxo-but-3-enyloxy) -5-hydroxy-4H-pyran-4-one)) and 5-methyl-2- (methylethyl) phenyl (2E) -3- (3, 4, 5-trimethoxyphenyl) prop-2-enoate (5-methyl-2- (methylethyl) phenyl (2E) -3- (3,4,5-trimethoxyphenyl) prop-2-enoate) Compound to Weight Ratio May be 1: 1-4. It is useful because the melting point of the two compounds within the weight ratio range is lowered, thereby reducing the time and the skin absorption rate can be enhanced. In view of the above, the weight ratio between the two compounds may be 1: 1.1-3.9, 1: 1.2-3.8, 1: 1.3-3.7, 1: 1.4-3.6 or 1: 1.5-3.5.

In the cosmetic composition which is an aspect of the present invention, the cosmetic composition comprises an emulsion.

In another aspect, the present invention relates to a method for enhancing the skin absorption rate of a cosmetic composition, which comprises mixing a polar oil with two compounds having a phenyl ring.

In another method of enhancing the skin absorption rate of the cosmetic composition of the present invention, the two compounds having the phenyl ring are 5-methyl-2- (methylethyl) phenyl (2E) -3- (3, 4, 5-trimethoxyphenyl) prop-2-enoate (5-methyl-2- (methylethyl) phenyl (2E) -3- (3,4,5-trimethoxyphenyl) prop-2-enoate) and 2- ((3E) -4 (2H, 3H-benzo [3, 4-d] 1, 3-dioxolan-5-yl) -2-oxo-but-3-enyloxy) -5-hydroxy-4H- Pyran-4-one) (2-((3E) -4 (2H, 3H-benzo [3, 4-d] 1, 3-dioxolan-5-yl) -2-oxo-but-3-enyloxy)- 5-hydroxy-4H-pyran-4-one)).

In a method of improving skin absorption of a cosmetic composition which is another aspect of the present invention, the 2-((3E) -4 (2H, 3H-benzo [3, 4-d] 1, 3-dioxolan-5-yl ) -2-oxo-but-3-enyloxy) -5-hydroxy-4H-pyran-4-one) (2-((3E) -4 (2H, 3H-benzo [3, 4-d] 1) , 3-dioxolan-5-yl) -2-oxo-but-3-enyloxy) -5-hydroxy-4H-pyran-4-one)) and 5-methyl-2- (methylethyl) phenyl (2E)- 3- (3, 4, 5-trimethoxyphenyl) prop-2-enoate (5-methyl-2- (methylethyl) phenyl (2E) -3- (3,4,5-trimethoxyphenyl) prop- 2-enoate) the weight ratio between the compounds may be 1: 1-4. It is useful because the melting point of the two compounds within the weight ratio range is lowered, thereby reducing the time and the skin absorption rate can be enhanced. In view of the above, the weight ratio between the two compounds may be 1: 1.1-3.9, 1: 1.2-3.8, 1: 1.3-3.7, 1: 1.4-3.6 or 1: 1.5-3.5.

In a method of enhancing the skin absorption rate of a cosmetic composition which is another aspect of the present invention, the cosmetic composition includes a method of enhancing the skin absorption rate of the cosmetic composition, which is an emulsion.

Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the following examples are provided only for the purpose of illustration in order to facilitate understanding of the present invention, the scope and scope of the present invention is not limited thereto.

Example 1 Melting Point Verification

A phase diagram was created to confirm the eutectic mixture properties of melalasolve and selenoids [FIG. 1]. Weigh 10 g of Melasolve and 10 g of Seletinoid G, respectively, and measure the melting point of the sample in which the initial concentration of Melasolve is adjusted from 100% to 0% using DSC (). Created. As a result, when only melasolv and serenoidoid G were present, each melting point was about 110 and 170 degrees, respectively. On the other hand, specifically, after mixing each compound in a weight ratio of 1: 2, it was confirmed that the melting point is lowered to 70 degrees.

 Example 2 Measurement of Dissolution Rate

The degree of dissolution was compared after the addition of the polar oil for cosmetic introduction of the eutectic mixture. That is, 20 g of a eutectic mixture, 10 g of melasolve, and 10 g of selenoid G were dissolved in 100 g of a mixture of cetylethylhexanoate and liquid paraffin 5: 5, and warmed to 60 degrees. Thereafter, by using a strainer to filter the active ingredient suspended without dissolving, and after removing the oil with alcohol, the mass was measured to determine the degree of melting relative to the initial content [Fig. 2]. As a result, the eutectic mixture showed a solubility of 80% or more after about 10 minutes, while the solubility of less than 30% in the case of a single product. As a result, it was confirmed that the eutectic mixture can significantly increase the dissolution rate and solubility compared to the single substance.

Example 3

Emulsion was prepared in the following composition using the dissolved eutectic mixture / oil, melasolve / oil, selenoid G / oil mixture in Example 2.

ingredient A B C Purified water To 100 To 100 To 100 PEG (20) sorbitan monolaurate One One 1.0 Eutectic Blends / Oils 10 0 0 Melasolve / Oil 0 10 0 Seletinoid G / Oil 0 0 10 Squalane
(Squalane) 5.0 5.0 5.0 Carbomer
(Carbomer) 0.5 0.5 0.5 Triethanolamine
(Triethanolamine) 0.5 0.5 0.5

Subsequently, the nanoemulsion was prepared by treating with 1,000bar / 3cycle through a manufactured high pressure emulsifier. In order to confirm the re-precipitation phenomenon of the active ingredient Melasolve and selenide G in the prepared nanoemulsion, the crystal phenomenon was confirmed by using a transmission electron microscope (TEM).

As a result, when the common mixture was used, nanoemulsions of about 200 nm were prepared without precipitation of the active ingredient (a), whereas in the rest of the cases, crystals precipitated and were hardly absorbed by the skin (b, c).

Example 4

Frantz cell test was conducted to evaluate the skin absorption rate of the nanoemulsion prepared in Example 3. As shown in FIG. 4, when the eutectic mixture of Example 3 was used, the highest skin absorption rate was confirmed (b), and in the case of the nanoemulsion used alone with the melasolve of Example 3 (c), which is a chemical enhancer. When propylene glycol / EtOH = 3/7 mixture was used (a), it showed high skin delivery rate.

Having described the specific part of the present invention in detail, it is apparent to those skilled in the art that the specific technology is merely a preferred embodiment, and the scope of the present invention is not limited thereto. Therefore, the substantial scope of the present invention will be defined by the appended claims and equivalents thereof.

Claims (8)

Two kinds of compounds having a phenyl ring and a polar oil,
The two compounds having the phenyl ring are 5-methyl-2- (methylethyl) phenyl (2E) -3- (3, 4, 5-trimethoxyphenyl) prop-2-enoate (5- methyl-2- (methylethyl) phenyl (2E) -3- (3,4,5-trimethoxyphenyl) prop-2-enoate) and 2-((3E) -4 (2H, 3H-benzo [3, 4-d ] 1,3-dioxolan-5-yl) -2-oxo-but-3-enyloxy) -5-hydroxy-4H-pyran-4-one) (2-((3E) -4 (2H, 3H-benzo [3, 4-d] 1, 3-dioxolan-5-yl) -2-oxo-but-3-enyloxy) -5-hydroxy-4H-pyran-4-one)) 1.5-3.5: Cosmetic composition containing by weight ratio of 1. The method of claim 1,
Two kinds of compounds having the phenyl ring is a cosmetic composition that is dissolved in polar oil. The method of claim 1,
5-methyl-2- (methylethyl) phenyl (2E) -3- (3,4,5-trimethoxyphenyl) prop-2-enoate (5-methyl-2- (methylethyl) phenyl ( 2E) -3- (3,4,5-trimethoxyphenyl) prop-2-enoate) and 2-((3E) -4 (2H, 3H-benzo [3, 4-d] 1, 3-dioxolane-5 -Yl) -2-oxo-but-3-enyloxy) -5-hydroxy-4H-pyran-4-one) (2-((3E) -4 (2H, 3H-benzo [3, 4-d) ], 3-dioxolan-5-yl) -2-oxo-but-3-enyloxy) -5-hydroxy-4H-pyran-4-one)) The weight ratio between the compounds is 2: 1, cosmetic composition. The method according to any one of claims 1 to 3,
The cosmetic composition is an emulsion, cosmetic composition Mixing two kinds of compounds having a phenyl ring and a polar oil,
The two compounds having the phenyl ring are 5-methyl-2- (methylethyl) phenyl (2E) -3- (3, 4, 5-trimethoxyphenyl) prop-2-enoate (5- methyl-2- (methylethyl) phenyl (2E) -3- (3,4,5-trimethoxyphenyl) prop-2-enoate) and 2-((3E) -4 (2H, 3H-benzo [3, 4-d ] 1,3-dioxolan-5-yl) -2-oxo-but-3-enyloxy) -5-hydroxy-4H-pyran-4-one) (2-((3E) -4 (2H, 3H-benzo [3, 4-d] 1, 3-dioxolan-5-yl) -2-oxo-but-3-enyloxy) -5-hydroxy-4H-pyran-4-one)) 1.5-3.5: A method for enhancing the skin absorption rate of the cosmetic composition, comprising a weight ratio of 1. The method of claim 5,
2 kinds of compounds having the phenyl ring are dissolved in polar oil, the method of enhancing the skin absorption rate of the cosmetic composition. The method of claim 5,
5-methyl-2- (methylethyl) phenyl (2E) -3- (3,4,5-trimethoxyphenyl) prop-2-enoate (5-methyl-2- (methylethyl) phenyl ( 2E) -3- (3,4,5-trimethoxyphenyl) prop-2-enoate) and 2-((3E) -4 (2H, 3H-benzo [3, 4-d] 1, 3-dioxolane-5 -Yl) -2-oxo-but-3-enyloxy) -5-hydroxy-4H-pyran-4-one) (2-((3E) -4 (2H, 3H-benzo [3, 4-d) ] 1, 3-dioxolan-5-yl) -2-oxo-but-3-enyloxy) -5-hydroxy-4H-pyran-4-one)) skin absorption of the cosmetic composition, the weight ratio between the compounds is 2: 1 How to promote. The method according to any one of claims 5 to 7, wherein the cosmetic composition is an emulsion.

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