TW201832756A - Transparent or semi-transparent oil-in-water type solubilizing agent and cosmetic composition comprising the same - Google Patents

Abstract

The present invention relates to a transparent or semi-transparent oil-in-water type solubilizing agent, which is used for transparent or semi-transparent oil-in-water formulations comprising a fat-soluble bioactive substance, and which comprises a polysorbate 20-cinnamic acid conjugate in which polysorbate 20 and cinnamic acid are combined, and a cosmetic composition comprising the same. The solubilizing agent and the composition comprising the same obtain an excellent dispersion stability of fat-soluble bioactive substances in a water phase.

Description

Translucent or translucent oil-based co-solvent in water and cosmetic composition containing same

The present invention relates to a light-transmitting or semi-light-transmitting oil-type co-solvent and a cosmetic composition including the same.

It is known that the fat-soluble bioactive substances used in the oil-water cosmetic preparations in the form of microbeads cannot be mutually soluble to form a light-transmitting or semi-light-transmitting formulation. Its use is limited to opaque or suspended formulations.

In order to use fat-soluble bioactive substances that are difficult to disperse in water-in-oil cosmetic formulations in water-soluble or semi-transparent water-in-oil cosmetic formulations (such as toners, essences, serums) It is necessary to introduce and combine a new surfactant.

[Citation List] [Patent Literature] [Patent Literature 1] Korean Patent Publication No. 10-2013-0106441 A [Patent Literature 2] Korean Patent Publication No. 10-2013-0125488 A [Patent Literature 3] Korean Patent Publication No. 10-2013-0052805 A

[technical problem]

In view of the above problems, the inventors of the present invention have studied a novel light-transmitting or semi-light-transmitting oil-based co-solvent and a light-transmitting or semi-light-transmitting water-oil cosmetic composition and completed the present invention.

One aspect of the present invention is to provide a light-transmitting or semi-light-transmitting oil-based co-solvent, which includes a novel polysorbate 20-cinnamic acid conjugate.

One aspect of the present invention is to provide a light-transmitting or semi-light-transmitting oil-in-water co-solvent, which obtains excellent water-dispersing stability in fat-soluble bioactive substances in a light-transmitting or semi-light-transmitting water-oil cosmetic composition.

One aspect of the present invention is to provide a co-solvent, which has excellent water-oil-solubilizing ability.

Another aspect of the present invention is to provide a cosmetic composition in the form of a light-transmitting or semi-light-transmitting oil-in-water formulation, including the light-transmitting or semi-light-transmitting oil-type co-solvent. [Problem solution]

One aspect of the present invention provides a co-solvent for a light-transmitting or semi-light-transmitting oil-water formulation including a fat-soluble bioactive substance, which includes a polysorbate 20-cinnamic acid conjugate, wherein polysorbate Ester 20 is combined with cinnamic acid.

In one aspect of the present invention, the fat-soluble bioactive substance is Melasolv.

In one aspect of the present invention, the transparent or translucent water-in-oil formulation has an average droplet size of 200 nm or less.

In one aspect of the present invention, mono-, di-, or tri-cinnamic acid is ester-bonded to a polysorbate 20-cinnamic acid conjugate to connect one of the hydroxyl groups of the polysorbate 20.

Another aspect of the present invention provides a cosmetic composition in the form of a light-transmitting or semi-light-transmitting oil-in-water formulation, which includes the co-solvent as described above and a fat-soluble bioactive substance.

In another aspect of the present invention, the cosmetic composition further includes a polycaprolactone-poly (ethylene glycol) block copolymer.

In another aspect of the present invention, the cosmetic composition further includes a polycaprolactone (PCL).

In another aspect of the present invention, the co-solvent content in the cosmetic composition is 100 to 300 parts by weight relative to 100 parts by weight of the fat-soluble bioactive substance.

In another aspect of the present invention, the weight ratio of the co-solvent to the polycaprolactone-poly (ethylene glycol) block copolymer in the cosmetic composition is 1: 1 to 10.

In another aspect of the present invention, the weight ratio of the co-solvent, the polycaprolactone-poly (ethylene glycol) block copolymer and the polycaprolactone in the cosmetic composition is 1: 1 to 5: 1 to 10. [Beneficial effects of the invention]

One aspect of the solubilizing agent of the present invention has an excellent solubilizing ability.

One aspect of the co-solvent of the present invention allows the use of fat-soluble bioactive substances conventionally used in opaque or suspension formulations for transparent or semi-transparent water-oil formulations.

One aspect of the co-solvent of the present invention has excellent solubilizing ability for fat-soluble bioactive substances with low solubilizing stability, especially at low temperatures.

The oil-water co-solvent of one aspect of the present invention achieves excellent dispersibility of a fat-soluble bioactive substance in water, which is difficult to disperse in water.

The cosmetic composition in the form of an oil-in-water formulation according to another aspect of the present invention has excellent dispersion stability in water.

The cosmetic composition in the form of an oil-in-water formulation according to another aspect of the present invention has excellent dispersion stability in water at cold temperatures.

Hereinafter, the present invention will be described in detail.

One aspect of the present invention provides a co-solvent for a light-transmitting or semi-light-transmitting oil-water formulation including a fat-soluble bioactive substance, which includes a polysorbate 20-cinnamic acid conjugate, wherein polysorbate Ester 20 is combined with cinnamic acid.

In a specific embodiment, the present invention may provide a method for preparing a light-transmitting or semi-light-transmitting oil-in-water formulation of a fat-soluble bioactive substance, which includes the following steps: Sorbitol 20-cinnamic acid conjugate treatment, in which polysorbate 20 is combined with cinnamic acid.

In another specific embodiment, the present invention may provide a polysorbate 20-cinnamic acid conjugate (wherein polysorbate 20 is combined with cinnamic acid) for preparing a light-transmitting material including one of a fat-soluble biologically active substance. Or the use of semi-transparent water oil preparations.

As used herein, the terms "translucent or semi-transparent oil-based co-solvent" and "co-solvent" refer to a surfactant used in transparent or semi-transparent oil formulations in which a large amount of water phase surrounds a small amount of oil Phase, and it is used to dissolve an oil phase or a fat-soluble component, which is insoluble in water to form a stable phase.

The term "co-solvent" as used herein is different from "emulsifier". The emulsifier is used in a composition having a milky appearance, and the co-solvent is used in a composition having a light-transmitting or semi-light-transmitting appearance.

As used herein, the term "transparent oil-in-water formulation" refers to a formulation in which the average size of the droplets represented by nano particles or cells is 80 nm or less. The term "translucent formulation" refers to a formulation that is white or bluish due to the light scattered by its particles, and wherein the average droplet size is 200 nm or less. The term "droplet size" refers to the length that passes through the longest straight line of the droplet, and the term "average droplet size" refers to a value obtained by the average droplet size.

As used herein, the term "fat-soluble bioactive substance" refers to a substance that is fat-soluble or hydrophobic. It means a substance used in a cosmetic composition which has a biologically active function that can be used in the human body, especially the skin. Specifically, the bioactive function may be whitening, anti-aging, anti-oxidation, improving skin elasticity or improving wrinkles. Preferably, the biologically active function may be whitening.

In one aspect of the present invention, the transparent or translucent water-in-oil formulation has an average droplet size of 200 nm or less. Specifically, the transparent or semi-transparent water-oil formulation has the following average droplet size: 200 nm or less, 190 nm or less, 180 nm or less, 170 nm or less, 160 nm or less Below, 150 nm or below, 140 nm or below, 120 nm or below, 100 nm or below, 90 nm or below, 85 nm or below, 80 nm or below, 75 nm or below, 70 nm or less, 65 nm or less, 60 nm or less, or 55 nm or less. The average droplet size may be 0.01 nm or more, 0.1 nm or more, 1 nm or more, 10 nm or more, 20 nm or more, or 50 nm or more.

In one aspect of the present invention, in the polysorbate 20-cinnamic acid conjugate, mono-, di-, or tri-cinnamic acid is connected to one of the hydroxyl groups of the polysorbate 20 by an ester bond.

Another aspect of the present invention provides a cosmetic composition in the form of a light-transmitting or semi-light-transmitting oil-water formulation, which includes any of the co-solvent and a fat-soluble bioactive substance.

In another aspect of the invention, the fat-soluble bioactive substance may be Melasolv.

In another aspect of the present invention, the cosmetic composition further includes a polycaprolactone-poly (ethylene glycol) block copolymer. This polycaprolactone-poly (ethylene glycol) block copolymer is also referred to as "PCG".

In another aspect of the present invention, the cosmetic composition further includes a polycaprolactone (PCL).

In another aspect of the present invention, the co-solvent content in the cosmetic composition is 100 to 300 parts by weight relative to 100 parts by weight of the fat-soluble bioactive substance. Specifically, the content of the co-solvent may be 100 parts by weight or more, 150 parts by weight or more, 160 parts by weight or more, 170 parts by weight or more with respect to 100 parts by weight of the fat-soluble bioactive substance. 180 parts by weight or more, 190 parts by weight or more, 200 parts by weight or more, or 210 parts by weight or more. In addition, the content of the co-solvent may be 300 parts by weight or less, 280 parts by weight or less, 260 parts by weight or less, 250 parts by weight or less, 240 parts by weight or less, 230 parts by weight or less, 220 parts by weight or less, 210 parts by weight or less, 200 parts by weight or less, 190 parts by weight or less, or 180 parts by weight or less. When the weight ratio of the co-solvent to the fat-soluble bioactive substance satisfies the above range, the fat-soluble bioactive substance in the composition has excellent dispersion stability in water.

In another aspect of the present invention, the present invention provides a cosmetic composition, wherein the weight ratio of the co-solvent to the PCG is 1: 1 to 10. Specifically, the weight ratio of the co-solvent to the PCG is 1: 1 or more, 1: 1.5 or more, 1: 2 or more, 1: 2.5 or more, 1: 3 or more, 1: 3.5 or more, 1: 4 or more, 1: 4.5 or more, 1: 4.8 or more, 1: 4.9 or more, 1: 5 or more, or 1: 7 or more. Moreover, the weight ratio of the co-solvent to the PCG may be 1:10 or less, 1: 9.5 or less, 1: 9 or less, 1: 8 or less, 1: 7.5 or less, 1: 7 or below, 1: 6.5 or below, 1: 6 or below, 1: 5.5 or below, 1: 5.4 or below, 1: 5.3 or below, 1: 5.2 or below, 1: 5.1 Or less, 1: 5 or less, 1: 4.5 or less, or 1: 4 or less. When the weight ratio of the co-solvent to the PCG satisfies the above range, the fat-soluble bioactive substance in the composition has excellent dispersion stability in water.

In another aspect of the present invention, the present invention provides a cosmetic composition, wherein the weight ratio of the co-solvent, the PCG and the polycaprolactone is 1: 1 to 5: 1 to 10. Specifically, the weight ratio of the co-solvent, the PCG and the polycaprolactone may be 1: 1.5 to 4.5: 2 to 8, and 1: 2 to 4: 3 to 7. Moreover, it may be 1: 2.5 to 3.5: 3 to 7. When the weight ratio of the co-solvent, the PCG and the polycaprolactone satisfies the above range, the fat-soluble bioactive substance in the composition has excellent dispersion stability in water.

In another aspect of the present invention, the composition is a skin external agent.

The topical agent for skin is a general term which covers any substance applied outside the skin and includes various formulated cosmetics. The skin external agent is not particularly limited, but may be, for example, a skin external agent for skin whitening, skin anti-aging, or skin antioxidant.

In another aspect of the invention, the composition is a cosmetic composition in the form of an oil-in-water (O / W) formulation.

The cosmetic composition in the form of an oil-in-water formulation is not particularly limited and may be appropriately selected depending on the purpose. For example, it may be made into a formulation selected from softening lotion (skin lotion), nourishing lotion, essence, nourishing cream cream, massage cream, pack, gel, essence, eye cream, eye essence, cleansing cream, cleansing Cleansing foam, cleansing water, pack, powder, body lotion, body cream, body oil, and body essence essence) group, but not limited to this.

The content of the fat-soluble bioactive substance is not particularly limited, but may be 0.0001 to 10% by weight relative to the total weight of the composition. When the active ingredient satisfies the above-mentioned content, it can exhibit excellent effects without side effects.

The cosmetic composition may also include a cosmetically acceptable excipient which, when applied to the skin, may act as a diluent, dispersant or carrier to facilitate the distribution of the composition.

In a specific embodiment, the composition is an oil-in-water (O / W) emulsion, preferably the amount of water in the emulsion may be at least 80% by weight of the excipient. However, the present invention is not limited to this, and any known cosmetically acceptable excipient can be used. The cosmetic composition may also include cosmetic adjuvants commonly used in the field of the present invention, such as: fatty substances, organic solvents, silicon, thickeners, emollients, Sunscreen agent, antifoaming agent, moisturizing agent, fragrance, preservative, surfactant, filler, sequestrant ), Cationic, anionic, nonionic or amphoteric polymer (cationic, anionic, nonionic or amphoteric polymer) or mixtures thereof, propellants, alkalizing or acidifying agents, dyes, Pigments or nanopigments (specifically, supplementary sun protection by physically blocking UV radiation) or other ingredients commonly used in cosmetics, especially sunscreen compositions. The organic solvent may be, for example, a lower alcohol or a polyhydric alcohol, such as ethanol, isopropanol, propylene glycol, glycerol, sorbitol, and the like. The lipid may be, for example, oil, wax or a mixture thereof, fatty acid, fatty acid ester, fatty alcohol, paraffin fat, paraffin, lanolin, hydrogenated lanolin, or acetylated lanolin. The oil may be a vegetable, mineral or synthetic oil, which is specifically selected from hydrogenated palm oil, hydrogenated castor oil, liquid paraffin grease, liquid paraffin, purcellin oil, volatile or non-volatile silicone oil, and Isoalkane.

In another aspect of the present invention, the composition may be a composition for skin whitening, skin anti-aging or skin antioxidant.

Therefore, in a specific embodiment, the present invention may provide a method for skin whitening, skin anti-aging, or skin anti-oxidation, which includes the following steps: implementing a composition in the form of a light-transmitting or translucent water-oil formulation To individuals in need, it includes any of the co-solvents and a fat-soluble bioactive substance.

In another specific embodiment, the present invention can provide a composition in the form of a light-transmitting or translucent water-in-oil formulation for skin whitening, skin anti-aging or skin anti-oxidation, comprising any of the co-solvents and a A fat-soluble bioactive substance is used as the active ingredient.

In another specific embodiment, the present invention can provide a composition comprising any of the co-solvent and a fat-soluble bioactive substance in the form of a light-transmitting or semi-light-transmitting water-oil formulation for preparing skin whitening and anti-aging skin. Or skin antioxidant composition use.

In another specific embodiment, the present invention may provide a composition comprising any of the co-solvent and a fat-soluble bioactive substance in the form of a light-transmitting or semi-light-transmitting water-oil formulation, which is used for skin whitening, skin Anti-aging or skin antioxidant.

Hereinafter, the present invention will be described in more detail with reference to examples. Those skilled in the art should clearly understand that these embodiments are only for illustrative purposes and the scope of the present invention should not be construed as being limited by these embodiments.

Example 1 : Preparation of polysorbate 20- cinnamic acid conjugate A surfactant known as Tween 20, polysorbate 20 has three hydroxyl groups (-OH). One to three cinnamic acids are attached to the hydroxyl group to prepare a polysorbate 20-cinnamic acid conjugate. The polysorbate 20 and the cinnamic acid used in the preparation were purchased from Sigma Aldrich. The synthesis method is as follows: 1.1 equivalents of DCC, 10 mol% of DMAP, and 4 equivalents of cinnamic acid are used per equivalent of Tween 20. First, Tween 20, DMAP and cinnamic acid were dissolved in 30 ml of dichloromethane with stirring at room temperature. DCC was also dissolved in 10 ml of dichloromethane and added dropwise to the previously prepared solution using a magnetic bar while stirring, while maintaining the temperature at 0 ° C using an ice bath. The reaction was then allowed to stir at room temperature for 3 hours. Then, DCU was filtered, and the solution was concentrated under reduced pressure. Precipitation was performed in 500 ml of ether, followed by filtration and drying to obtain Tween 20-CA. The synthetic method is shown in FIG. 1. A compound was obtained by the above synthesis method, and the structure of the compound was confirmed by NMR. The NMR data are shown in FIG. 2. Although this NMR data shows that polysorbate 20 combined with cinnamic acid is obtained, it does not correctly show how much cinnamic acid will react with OH groups. However, the confirmed combination of cinnamic acid and polysorbate 20 indicates that cinnamic acid is linked to the most active OH.

Preparation of Compositions 1 to 7 Compositions 1 to 7 were prepared using the polysorbate 20-cinnamic acid conjugate obtained in Example 1 based on the component amounts shown in Table 1 below. PCG was purchased from AT Lab, Melasolv was purchased from LEAD GENE and PCL was purchased from Sigma Aldrich. Table 1

Test Example 1 : Low-temperature stability test - Measurement of particle size and PDI value It was evaluated whether the compositions 1 to 7 had precipitated immediately after preparation and 4 weeks later. The particle size and PDI value of the composition that was not precipitated were measured at low and high temperatures. Zetasizer (mode: Nano ZS, Malvern) was used to measure particle size and PDI value. The PDI value ranges from 0 to 1. When the PDI value is 0, its distribution is close to a monodisperse distribution, and when it is close to 1, its distribution becomes more polydisperse. The low temperature is 4 ° C, the room temperature is RT, and the high temperature is 45 ° C. The measurement results are shown in Table 2. Table 2

The 4-week stability evaluation results show that the composition including Example 1 of the present invention is superior to the composition including each of Tween 20 and cinnamic acid in terms of solubilizing ability. In particular, the most effective results are obtained when a PCG surfactant and a co-surfactant are used together as the main surfactant.

Examples of the formulation of the composition of the present invention will be described below. However, these examples are for illustrative purposes only and the scope of the present invention is not intended to be limited by these examples.

Preparation Example 1: Toner (Toner) Table 3

Although the present invention has been specifically shown and described with reference to specific embodiments, those skilled in the art will understand that such specific embodiments are merely preferred specific embodiments and the scope of the present invention is not limited thereto. Accordingly, the actual scope of the present invention will be defined by the scope of the attached patent applications and their equivalents.

no

FIG. 1 shows a method for preparing the co-solvent of Example 1 of the present invention. FIG. 2 shows NMR data of the co-solvent prepared according to Example 1 of the present invention.

Claims (11)

A cosolvent for a light-transmitting or semi-light-transmitting oil-in-water formulation comprising a fat-soluble bioactive substance, comprising a polysorbate 20-cinnamic acid conjugate, wherein polysorbate 20 is combined with cinnamic acid . The co-solvent according to claim 1, wherein the fat-soluble bioactive substance is Melasolv. The co-solvent according to claim 1, wherein the transparent or semi-transparent water-in-oil formulation has an average droplet size of 200 nm or less. The co-solvent according to claim 1, wherein the transparent or semi-transparent water-in-oil formulation has an average droplet size of 80 nm or less. The co-solvent according to claim 1, wherein one, two or three cinnamic acid in the polysorbate 20-cinnamic acid conjugate is connected to one of the hydroxyl groups of the polysorbate 20 with an ester bond. A cosmetic composition in the form of a light-transmitting or translucent oil-in-water formulation, comprising a co-solvent as described in claims 1 to 5 and a fat-soluble bioactive substance. The cosmetic composition according to claim 6, wherein the cosmetic composition further comprises a polycaprolactone-poly (ethylene glycol) block copolymer. The cosmetic composition according to claim 7, wherein the cosmetic composition further comprises a polycaprolactone. The cosmetic composition according to claim 6, wherein the content of the co-solvent in the cosmetic composition is 100 to 300 parts by weight relative to 100 parts by weight of the fat-soluble bioactive substance. The cosmetic composition according to claim 7, wherein the weight ratio of the co-solvent to the polycaprolactone-poly (ethylene glycol) block copolymer is 1: 1 to 10. The cosmetic composition according to claim 8, wherein the weight ratio of the co-solvent, the polycaprolactone-poly (ethylene glycol) block copolymer to the polycaprolactone is 1: 1 to 5: 1 to 10.