WO2018128465A1 - Solubilizing agent for transparent or translucent oil-in-water formulation and cosmetic composition comprising same - Google Patents

Abstract

The present specification relates to a solubilizing agent for a transparent or translucent oil-in-water formulation and a cosmetic composition comprising the same, wherein the solubilizing agent is used in a transparent or translucent oil-in-water formulation comprising a fat-soluble physiologically active substance, and comprises a polysorbate 20-cinnamic acid conjugate in which polysorbate 20 is bonded to a cinnamic acid. The solubilizing agent and a composition comprising the same have excellent water dispersion stability with respect to a water phase of the fat-soluble physiologically active substance.

Description

Solubilizers for transparent or translucent oil-in-water formulations and cosmetic compositions comprising the same

The present specification relates to a novel solubilizer for transparent or translucent oil-in-water formulations and a cosmetic composition comprising the same.

In oil-in-water cosmetic formulations, fat-soluble physiologically active substances used in the form of conventional microbeads are solubilized and are not used transparently or semitransparently, but are limited to opaque or suspended formulations.

It is necessary to introduce and combine new surfactants to use oil-soluble bioactive substances which are difficult to disperse in oil-in-water cosmetic formulations in oil-in-water cosmetic formulations such as transparent or translucent skins, essences and serums.

[Preceding technical literature]

[Patent Documents]

(Patent Document 1) Korean Patent Publication No. 10-2013-0106441 A

(Patent Document 2) Korean Patent Publication No. 10-2013-0125488 A

(Patent Document 3) Korean Patent Publication No. 10-2013-0052805 A

In view of the above problems, the inventors of the present invention have led to the present invention by studying a novel transparent or translucent oil-in-water solubilizer and a transparent or translucent oil-in-water cosmetic composition comprising the same. .

One aspect of the present invention is to provide a solubilizing agent for transparent or translucent oil-in-water formulations comprising the novel polysorbate 20-cinnamic acid conjugate.

One aspect of the present invention is to provide a solubilizing agent for a transparent or translucent oil-in-water type having excellent water-phase stability of the fat-soluble bioactive substance in the cosmetic composition of the transparent or translucent oil-in-water formulation.

One aspect of the present invention is to provide a solubilizer excellent in oil-in-water solubility.

Another aspect of the present invention is to provide a cosmetic composition of a transparent or translucent oil-in-water formulation comprising the solubilizer for the transparent or translucent oil-in-water type.

One aspect of the present invention is used in a transparent or translucent oil-in-water formulation containing a fat-soluble bioactive material, the polysorbate 20 and the cinnamic acid (cinnamic acid) combined Provided are solubilizers for transparent or translucent oil-in-water formulations comprising polysorbate 20-cinnamic acid conjugates.

In one aspect of the invention, the fat-soluble bioactive material provides a solubilizer, which is a melazole.

In one aspect of the invention, the transparent or translucent oil-in-water formulation provides a solubilizing agent having an average size of droplets of 200 nm or less.

In one aspect of the invention, the polysorbate 20-cinnamic acid conjugate provides a solubilizer in which 1, 2 or 3 cinnamic acid esters are bonded to the hydroxyl group of polysorbate 20.

Another aspect of the present invention provides a cosmetic composition of a transparent or translucent oil-in-water formulation comprising a solubilizer and a fat-soluble bioactive substance according to any one of the above.

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

In another aspect of the invention, the cosmetic composition further comprises a polycaprolactone (Polycaprolactone, PCL), provides a cosmetic composition.

In another aspect of the present invention, the solubilizer is provided based on 100 parts by weight of fat-soluble bioactive material, provides a cosmetic composition.

In another aspect of the present invention, the weight ratio of the solubilizer and the polycaprolactone-poly (ethylene glycol) block copolymer is 1: 1 to 10, to provide a cosmetic composition.

In another aspect of the invention, the solubilizer, polycaprolactone-poly (ethylene glycol) block copolymer and polycaprolactone weight ratio of 1: 1 to 5: 1 to 10, provides a cosmetic composition.

Solubilizer according to an aspect of the present invention is excellent in solubility.

Solubilizer according to an aspect of the present invention has the effect that can be used as a transparent or translucent oil-in-water formulation of the fat-soluble physiologically active substance used in the previously opaque or suspended formulations.

Solubilizing agent according to an aspect of the present invention is excellent in solubilizing power for a fat-soluble physiologically active substance having a low solubilization stability, especially in cold.

Oil-in-water solubilizer according to an aspect of the present invention is excellent in water dispersion effect on the fat-soluble physiologically active substance difficult to disperse.

Cosmetic composition of oil-in-water formulation according to another aspect of the present invention is excellent in water dispersion stability.

Cosmetic composition of oil-in-water formulation according to another aspect of the present invention is excellent in water dispersion stability at cold temperature.

1 is a method for preparing a solubilizer according to the first embodiment of the present invention.

2 is NMR data of a solubilizer prepared according to Example 1 of the present invention.

Hereinafter, the present invention will be described in detail.

One aspect of the present invention is used in a transparent or translucent oil-in-water formulation containing a fat-soluble bioactive material, the polysorbate 20 and the cinnamic acid (cinnamic acid) combined Provided are solubilizers for transparent or translucent oil-in-water formulations comprising polysorbate 20-cinnamic acid conjugates.

In one embodiment, a method for preparing a transparent or translucent oil-in-water formulation containing a fat-soluble bioactive material, comprising polysorbate 20 and cinnamic acid Provided is a method for preparing a transparent or translucent oil-in-water formulation comprising treating a polysorbate 20-cinnamic acid conjugate to a fat-soluble physiologically active substance. can do.

In another embodiment, a fat-soluble bioactive substance, which is used as a polysorbate 20-cinnamic acid conjugate in which polysorbate 20 and cinnamic acid are combined. It is possible to provide a use for the preparation of a transparent or translucent oil-in-water formulation comprising a. In the present specification, "transparent or translucent oil-in-water formulation of Solubilizers "or" Solubilizers "are surfactants used in transparent or translucent oil-in-water formulations in which a large amount of water contains a small amount of oil phase, and dissolve oil-soluble or oil-soluble components that are insoluble in the water phase. It is a substance for the purpose of forming a stable phase.

In this specification, "solubilizer" and "emulsifier" are distinguished, and emulsifiers are used in compositions having a milky white appearance, while solubilizers are used in compositions having a transparent or translucent appearance.

As used herein, "transparent oil-in-water formulation" means that the average size of droplets represented by nanoparticles or micelles in the formulation is 80 nm or less. In addition, "translucent formulation" means that the light is scattered by the particles to give a white or slightly blue light, and the mean size of the droplets is 200 nm or less. The " droplet size " is the length of the still long line passing through the droplet, and " average size of the droplet " is the average value of the droplet sizes.

In the present specification, "lipophilic physiologically active substance" is a substance exhibiting fat-soluble or hydrophobic properties when used in a cosmetic composition, a substance exhibiting a physiologically active function useful for the human body, especially the skin. Specifically, the bioactive function may be whitening, anti-aging, antioxidant, skin elasticity enhancement or wrinkle improvement. Preferably the bioactive function may be whitening.

In one aspect of the invention, the transparent or translucent oil-in-water formulation provides a solubilizing agent having an average size of droplets of 200 nm or less. Specifically, the transparent or translucent oil-in-water formulation has an average size of droplets of 200 nm or less, 190 nm or less, 180 nm or less, 170 nm or less, 160 nm or less, 150 nm or less, 140 nm or less, 120 nm or less, 100 nm or less, 90 nm or less, 85 nm or less, 80 nm or less, 75 nm or less, 70 nm or less, 65 nm or less, 60 nm or less, or 55 nm or less. In addition, the droplets may have an average size of at least 0.01 nm, at least 0.1 nm, at least 1 nm, at least 10 nm, at least 20 nm, or at least 50 nm.

In one aspect of the invention, the polysorbate 20-cinnamic acid conjugate provides a solubilizer in which 1, 2 or 3 cinnamic acid esters are bonded to the hydroxyl group of polysorbate 20.

Another aspect of the present invention provides a cosmetic composition of a transparent or translucent oil-in-water formulation comprising a solubilizing agent of any one of the above solubilizing agents and a fat-soluble bioactive substance.

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

In another aspect of the invention, the cosmetic composition further comprises a polycaprolactone-poly (ethylene glycol) block copolymer (Polycaprolactone-poly (ethylene glycol) block copolymer), provides a cosmetic composition. The polycaprolactone-poly (ethylene glycol) block copolymer is also called "PCG".

In another aspect of the invention, the cosmetic composition further comprises a polycaprolactone (Polycaprolactone, PCL), provides a cosmetic composition.

In another aspect of the present invention, the solubilizer is provided based on 100 parts by weight of fat-soluble bioactive material, provides a cosmetic composition. Specifically, the solubilizer is 100 parts by weight, 150 parts by weight, 160 parts by weight, 170 parts by weight, 180 parts by weight, 190 parts by weight, 200 parts by weight or more based on 100 parts by weight of the fat-soluble physiologically active substance. Or 210 parts by weight or more. In addition, the solubilizer is 300 parts by weight or less, 280 parts by weight, 260 parts by weight, 250 parts by weight, 240 parts by weight, 230 parts by weight, 220 parts by weight or less, based on 100 parts by weight of a fat-soluble bioactive substance. It may be 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 solubilizer and the fat soluble bioactive substance satisfies the above range, the dispersion stability of the fat soluble bioactive substance in the composition is excellent.

In another aspect of the present invention, the weight ratio of the solubilizer and PCG is 1: 1 to 10, to provide a cosmetic composition. Specifically, the weight ratio of the solubilizer to 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. In addition, the weight ratio of the solubilizer and PCG is 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 less, 1: 6.5 or less, 1: 6 or less, 1 : 5.5 or less, 1: 5.4 or less, 1: 5.3 or less, 1: 5.2 or less, 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 solubilizer to the PCG satisfies the above range, the dispersion stability of the fat-soluble bioactive substance in the composition is excellent.

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

In another aspect of the invention, the composition is a topical skin composition.

The external preparation for the skin is a generic term that may include anything applied outside the skin, and cosmetics of various formulations may be included therein. The skin external preparation is also not particularly limited, but may be, for example, a skin external preparation for skin whitening, skin anti-aging or skin antioxidant.

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

The cosmetic composition of the oil-in-water formulation is not particularly limited in formulation, and may be appropriately selected as desired. For example, supple cream (skin lotion), nourishing cream, essence, nourishing cream, massage cream, pack, gel, essence, eye cream, eye essence, cleansing cream, cleansing foam, cleansing water, pack, powder, body lotion, It may be prepared in any one or more formulations selected from the group consisting of body creams, body oils and body essences, but is not limited thereto.

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

The cosmetic composition may also include cosmetically acceptable excipients that act as diluents, dispersants or carriers so that the composition is easy to distribute when applied to the skin.

In one embodiment, the composition is an oil-in-water (O / W) emulsion, and the emulsion may preferably contain water in an amount of at least 80% by weight of the excipient. However, the present invention is not limited thereto, and any known excipient that is acceptable for cosmetic use may be used. In addition, the cosmetic composition is a cosmetic auxiliary agents commonly used in the field of the present invention, such as fatty substances, organic solvents, silicon, thickeners, softeners, supplemental sunscreens, foam inhibitors, moisturizers, fragrances, preservatives, surface active agents, Total materials, containment agents, cationic, anionic, nonionic or amphoteric polymers or mixtures thereof, propellants, basicizing or acidifying agents, dyes, pigments or nanopigments (particularly in the case of UV radiation physically) By blocking to provide a supplementary photoprotective effect), or other components commonly used in cosmetics, in particular in the manufacture of sunscreen compositions. Among the organic solvents, lower alcohols and polyols such as ethanol, isopropanol, propylene glycol, glycerol, sorbitol and the like can be mentioned. Fatty substances may consist of oils or waxes or mixtures thereof, fatty acids, fatty acid esters, fatty alcohols, petrolatum, paraffin, lanolin, lanolin hydride or acetylated lanolin. The oil may be selected from vegetable, mineral or synthetic oils, in particular from hydrogenated palm oil, hydrogenated castor oil, liquid petrolatum, liquid paraffin, purcellin oil, volatile or nonvolatile silicone oil and isoparaffin.

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

Thus, in one embodiment comprising the step of administering to a subject in need thereof a composition of a transparent or translucent oil-in-water formulation comprising a solubilizing agent of any one of the solubilizing agents and a fat-soluble bioactive material. Skin whitening, skin anti-aging, or skin antioxidant can be provided.

In another embodiment, a transparent or translucent oil-in-water for skin whitening, skin anti-aging, or skin antioxidant, comprising a solubilizing agent and a fat-soluble physiologically active substance of any one of the solubilizing agents. The composition of the formulation may be provided.

In another embodiment transparent or translucent oil-in-water comprising a solubilizing agent of any of the above solubilizing agents and a fat-soluble bioactive material for use in the preparation of a composition for whitening, skin anti-aging, or skin antioxidants. water) may be used for the composition of the formulation.

In another embodiment a transparent or translucent oil-in-water formulation comprising a solubilizing agent of any of the above solubilizing agents and a fat soluble bioactive material for use in skin whitening, skin anti-aging, or skin antioxidants. A composition can be provided.

Hereinafter, the present invention will be described in more detail with reference to Examples. These examples are only for illustrating the present invention, and it will be apparent to those skilled in the art that the scope of the present invention is not to be construed as being limited by these examples.

Example 1 Preparation of Polysorbate 20-cinnamic Acid Conjugate

Polysorbate 20, also known as tween 20, has three hydroxyl groups (-OH). A polysorbate 20-cinnamic acid conjugate was prepared by combining 1 to 3 cinnamic acid with the hydroxyl group. Polysorbate 20 and cinnamic acid used in the production were purchased from sigma aldrich.

The synthesis method is as follows. The experiment was carried out with DCC 1.1, DMAP mol 10%, and cinnamic acid 4 equivalents based on the Tween 20 equivalent ratio 1. First, dissolve tween 20, DMAP and cinnamic acid by stirring in 30 ml of Methylene chloride at room temperature. DCC is also dissolved in 10 ml of Methylene chloride, and the solution is prepared dropwise while maintaining the solution at 0 degrees with an ice bath and stirring with a magnetic bar. The reaction is then stirred at room temperature for 3 hours, after which the DCU is filtered and the solution is concentrated under reduced pressure. Precipitate in 500 ml of Ether, filter and dry to obtain tween 20-CA. The synthesis method is shown in FIG.

The compound according to the above synthesis was obtained, and the structure of the compound was confirmed by NMR. NMR data was as shown in FIG. As a result, polysorbate 20 synthesized with cinnamic acid was obtained using NMR data, but the NMR data could not accurately distinguish how many cinnamic acid reacted in a portion of the OH group. However, by confirming the results of the synthesis of cinnamic acid and polysorbate 20, it could be estimated that the cinnamic acid is bound to the most reactive OH.

Preparation of Compositions 1-7

Using the polysorbate 20-cinnamic acid conjugate prepared in Example 1 to prepare a composition 1 to 7 in the content as shown in Table 1. PCG was purchased from AT Lab, Melazolb from LEAD GENE, and PCL from Sigma Aldrich.

Number	Melasolv (g)	Tween 20 (g)	PCG (g)	PCL (g)	Cinnamic acid (g)	Tween 20-CA (g) (Example 1)	DW (g)
Composition 1	One						to 100
Composition 2	One		10	5			to 100
Composition 3	One	One			One		to 100
Composition 4	One					2	to 100
Composition 5	One	One	10	5	One		to 100
Composition 6	One		10	5		2	to 100
Composition 7			10	5		2	to 100

Experimental Example 1. Cold stability test-particle size and PDI value measurement

Precipitation immediately after the preparation of the compositions 1 to 7 and after 4 weeks was evaluated, and the composition that did not precipitate was measured for particle size and PDI values at cold and high temperatures. Particle size and PDI values were measured using a Zetasizer (model name: Nano ZS Malvern). PDI values can be interpreted as having a value from 0 to 1, with 0 being close to monodispersion and increasing to 1 having polydispersity distribution.

Cold temperature was observed at 4 ℃, room temperature was RT, high temperature was 45 ℃. The measurement results were shown in Table 2.

	Right after manufacturing		High temperature after 4 weeks		After 4 weeks at room temperature		Cold after 4 weeks
	Size	PDI	Size	PDI	Size	PDI	Size	PDI
1_M (Composition 1)	Precipitation	Precipitation	Precipitation	Precipitation	Precipitation	Precipitation	Precipitation	Precipitation
2_MPP (Composition 2)	122.6	0.245	125.6	0.162	132.2	0.132	180.5	0.256
3_MTC (Composition 3)	Precipitation	Precipitation	Precipitation	Precipitation	Precipitation	Precipitation	Precipitation	Precipitation
4_MC2 (Composition 4)	46.5	0.26	Precipitation	Precipitation	Precipitation	Precipitation	Precipitation	Precipitation
5_MTPPC (Composition 5)	122.4	0.112	136.8	0.256	128.9	0.32	265.3	0.423
6_MPPC2 (Composition 6)	130.5	0.111	135.1	0.142	128.6	0.132	129.2	0.122
7_PPC2 (Composition 7)	125.2	0.121	130.2	0.112	126.2	0.123	124.3	0.126

As a result of the 4-week stability evaluation, the solubilizing power of the composition including Example 1 according to an aspect of the present invention was superior to the composition using tween 20 and cinnamic acid, respectively. In particular, it was most effective to use PCG surfactant as the main and to introduce cosurfactant.

Hereinafter, the formulation example of the composition according to the present invention will be described, which is intended to explain in detail only, not intended to limit the present invention.

Formulation Example 1 Flexible Cosmetic (Skin Lotion)

Compounding ingredient	Content (weight%)
Melazolb	0.001
glycerin	3.0
Butylene glycol	2.0
Propylene glycol	2.0
Carboxy Vinyl Polymer	0.1
Fiji-12 nonylphenyl ether	0.2
Example 1	0.4
ethanol	10.0
Triethanolamine	0.1
Preservative, coloring, flavoring	Quantity
Purified water	Remaining amount

As described above in detail the specific parts of the present invention, it is apparent to those skilled in the art that such specific description is merely a preferred embodiment, thereby not limiting the scope of the present invention. something to do. Thus, the substantial scope of the present invention will be defined by the appended claims and their equivalents.

Claims (11)

1. Polysorbate 20-cinnamic acid combined with polysorbate 20 and cinnamic acid, used in transparent or translucent oil-in-water formulations containing fat-soluble bioactive substances Solubilizer for transparent or translucent oil-in-water formulations comprising a conjugate (polysorbate 20-cinnamic acid conjugate).
2. The method of claim 1,

   The fat-soluble bioactive substance is a melazole, solubilizer.
3. The method of claim 1,

   Solubilizing agent wherein the transparent or translucent oil-in-water formulation has a mean size of 200 nm or less.
4. The method of claim 1,

   Solubilizing agent wherein the transparent or translucent oil-in-water formulation has an average size of droplets of 80 nm or less.
5. The method of claim 1,

   The polysorbate 20-cinnamic acid conjugate is a solubilizer in which 1, 2 or 3 cinnamic acid esters are bonded to the hydroxyl group of polysorbate 20.
6. Cosmetic composition of a transparent or translucent oil-in-water formulation comprising a solubilizer according to any one of claims 1 to 5 and a fat-soluble physiologically active substance.
7. The method of claim 6,

   The cosmetic composition further comprises a polycaprolactone-poly (ethylene glycol) block copolymer (Polycaprolactone-poly (ethylene glycol) block copolymer), cosmetic composition.
8. The method of claim 7, wherein

   The cosmetic composition further comprises a polycaprolactone (Polycaprolactone), cosmetic composition.
9. The method of claim 6,

   The solubilizer is contained in 100 to 300 parts by weight based on 100 parts by weight of a fat-soluble bioactive material, cosmetic composition.
10. The method of claim 7, wherein

    The weight ratio of the solubilizer and the polycaprolactone-poly (ethylene glycol) block copolymer is 1: 1 to 10, cosmetic composition.
11. The method of claim 8,

    The weight ratio of the solubilizer, polycaprolactone-poly (ethylene glycol) block copolymer and polycaprolactone is 1: 1 to 5: 1 to 10, cosmetic composition.

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