KR101378554B1 - Ultraviolet blocking composition and method of fabricating the same - Google Patents

Abstract

The present invention relates to a sunscreen composition and a method for preparing the same. According to one embodiment of the present invention, a hydrophobic liquid polymer medium; And a sunscreen active agent impregnated in the hydrophobic liquid polymer medium.

Description

Ultraviolet blocking composition and method of manufacturing the same

The present invention relates to a pharmacological composition having a sunscreen function, and more particularly, to a sunscreen composition and a method for preparing the same.

The sun's rays consist of γ-rays, X-rays, ultraviolet rays, visible rays, infrared rays, and radio waves of different wavelengths, and the ultraviolet rays are ultraviolet rays A (320-400 nm), ultraviolet rays B (290-320 nm) and UV-C can be divided into (200 ~ 290nm). In general, exposure of the human body to ultraviolet light can result in short or long term skin damage, such as erythema, burns, wrinkles, freckles, keratinism or skin cancer. In particular, it is known that when exposed to UVA, the immune system may be weakened and skin cancer may also be caused. Recently, due to the destruction of the ozone layer by the air pollution source and the increase of leisure activity, the human body is more exposed to the danger of ultraviolet rays, and thus, efforts to protect the human body from ultraviolet rays are more urgent.

Materials having a sunscreen function may be divided into inorganic ultraviolet scatterers that absorb or scatter ultraviolet rays and organic ultraviolet absorbers that absorb ultraviolet rays and convert energy into various forms such as heat, waves, fluorescence, and radicals. The inorganic ultraviolet scattering agent is mainly formed of a metal oxide, and has a high refractive index, so the light scattering effect is large, and there is little deterioration problem such as decomposition or denaturation in the latter organic ultraviolet absorber. However, the inorganic ultraviolet scattering agent has a disadvantage in that there is a clouding phenomenon because of dispersing visible light, and a feeling of fluttering when the skin is applied. Relatively organic UV absorbers have a good feeling of use and have a high extinction coefficient. However, since the organic ultraviolet absorber is chemically synthesized, it is known as a suspected irritant that causes skin irritation, phototoxicity, or endocrine disruption.

For the reasons described above, there is a demand for the development of a sunscreen active agent having improved safety for human body while having excellent usability. Recently, as a natural light absorbing active compound, light absorbing active substances such as phenolic compounds, betaines, and carotinoids, which are plant-derived light absorbing active compounds, have been studied. Dual phenolic compounds have been reported to exhibit excellent absorption of ultraviolet light, optionally without color. Phenolic compounds in plants have been known to protect themselves from pathogens or herbivores, but recent studies have reported that they play an important role in the photoprotective function of protecting against photodamage in plants. .

However, these natural light-absorbing active compounds are mostly poorly soluble in spite of their excellent UV-absorbing activity, making it very difficult to apply them as highly concentrated sunscreen cosmetics. Therefore, in the conventional sunscreen cosmetics produced using a natural light absorbing active compound, generally, a synthetic organic UV absorber having improved solubility in order to secure UV blocking ability together with the natural light absorbing active compound, for example, From 5% to 15% by weight. However, such synthetic organic ultraviolet absorbents have poor skin medical stability as described above, and their application needs to be limited.
Related Prior Art Literature
[Patent Document 1] Korean Patent Publication No. 10-2008-0040868
[Patent Document 2] Korean Patent Publication No. 10-2013-0109653
[Patent Document 3] Korean Patent Publication No. 10-2012-0058940

SUMMARY OF THE INVENTION The present invention has been made in an effort to provide a sunscreen composition capable of high concentration of a poorly soluble natural light absorbing active compound to obtain an excellent sunscreen effect without the application of a synthetic organic UV absorber.

Another technical problem to be achieved by the present invention is to provide a method for preparing a sunscreen composition having the above-described advantages and easy production and excellent reproducibility.

According to an embodiment of the present invention for achieving the above technical problem, a hydrophobic liquid polymer medium; And a sunscreen active agent impregnated in the hydrophobic liquid polymer medium. The hydrophobic liquid polymer medium is any one selected from the group consisting of polyglycerine, polypropyleneglycol, hydrogenated polyiosbutene, and hydrogenated polydodecene. It can include a combination of.

In some embodiments, the weight ratio of the sunscreen active agent to the hydrophobic liquid polymer medium may be 1/9 to 1/2. The sunscreen active agent may include any one or combination of phenolic acid-based compounds and flavonoid-based compounds and derivatives thereof.

The phenolic acid compound is ferulic acid (ferulic acid), caffeic acid (caffeic acid), coumaric acid (coumaric acid), alpha-cyanohydroxyhydroxynamic acid (Alpha-cyano-4-hydroxycinnamic acid), chicory acid (Cichoric acid) acid, Cinnamic acid, Chlorogenic acid, Caftaric acid, Coutaric acid, Fertaric acid, Deferulic acid It may include any one or a combination thereof selected from the group consisting of Sinapinic acid and derivatives thereof.

The flavonoid-based compound is quercetin (quercetin), camphorol (kaempherol, apigenin), luteolin (Luteolin), myricetin (myricetin), Tangerine (Tangeritin (4 ', 5, 6, 7, 8-) pentamethoxyflavone)), chrysin (5,7-OH), baicalein (5,6,7-trihydroxyflavone), cutellarein (5,6,7,4'-tetrahydroxyflavone), Wogonin (5,7 -OH, 8 -OCH ₃ ), azeleatin, fisetin, galangin, gosysytin, kaempferide, iso Raminetin, Morin, Natsudaidain, Pachypodol, Rhamnazin, Rhamnetin, Astragalin, Azalein, Azalein, Hyperside, isoquercitin, kaempferitrin, myricitrin, quercitrin, robinin, rutin, spireoside Spiraeoside, Xanthorhamnin, Amuresin ( Amurensin), Icariin (Icariin), Troxerutin (Troxerutin) and derivatives thereof may include any one selected from the group or a combination thereof.

In some embodiments, the sunscreen composition may further comprise an alcoholic compound dissolved in a hydrophobic liquid polymer medium. The content of the alcohol-based compound may be 0.1 wt% to 30 wt% with respect to the total weight of the sunscreen composition. In some embodiments, the alcohol-based compound may include any one or a combination of two or more selected from the group consisting of ethanol, glycerin, propylene glycol, butylene glycol, dipropylene glycol, and derivatives thereof. .

According to an embodiment of the present invention for achieving the above another technical problem, adding a organic solvent to a hydrophobic liquid polymer medium to prepare a first mixed solution; Preparing a second mixed solution by adding and stirring a sunscreen activator in the first mixed solution; And removing the organic solvent in the second mixed solution to obtain a sunscreen composition comprising a sunscreen activator impregnated in the hydrophobic liquid polymer medium.

The organic solvent may include ethanol, methanol, acetone, tetrahydrofuran (THF: Tetrahydrofuran), acetonitrile, derivatives thereof, or mixtures thereof. In some embodiments, the sunscreen active agent comprises a first sunscreen activator and a second sunscreen activator different from the first sunscreen activator, wherein preparing the second mixed solution comprises: Sequentially dissolving the first sunscreen active agent and the second sunscreen active agent.

In some embodiments, before adding the sunscreen active agent, the step of adding and stirring the alcohol-based compound in the first mixed solution may be further performed. The content of the alcohol-based compound may be 0.1 wt% to 30 wt% with respect to the total weight of the sunscreen composition. The alcohol compound may include any one or a combination of two or more selected from the group consisting of ethanol, glycerin, propylene glycol, butylene glycol, and dipropylene glycol and derivatives thereof.

Removing the organic solvent may be performed by vacuum distillation, vacuum drying, or a combination thereof. In the second mixed solution, the weight ratio of the sunscreen active agent to the hydrophobic liquid polymer medium may be 1/9 to 1/2. In addition, the sunscreen active agent may include any one or a combination of phenolic acid-based compounds and flavonoid-based compounds.

In some embodiments, the phenolic acid-based compound is ferulic acid (ferulic acid), caffeic acid (caffeic acid), coumaric acid (coumaric acid), alpha cyano-4-hydroxycinnamic acid (Alpha-cyano-4-hydroxycinnamic acid), Cichoric acid, Cinnamic acid, Chlorogenic acid, Caftaric acid, Coutaric acid, Fertaric acid, Diferric It may include any one selected from the group consisting of acid (Diferulic acid), Sinapinic acid (Sinapinic acid) and derivatives thereof or a combination thereof.

The flavonoid-based compound is quercetin (quercetin), camphorol (kaempherol, apigenin), luteolin (Luteolin), myricetin (myricetin), Tangerine (Tangeritin (4 ', 5, 6, 7, 8-) pentamethoxyflavone)), chrysin (5,7-OH), baicalein (5,6,7-trihydroxyflavone), cutellarein (5,6,7,4'-tetrahydroxyflavone), Wogonin (5,7 -OH, 8 -OCH ₃ ), azeleatin, fisetin, galangin, gosysytin, kaempferide, iso Raminetin, Morin, Natsudaidain, Pachypodol, Rhamnazin, Rhamnetin, Astragalin, Azalein, Azalein, Hyperside, isoquercitin, kaempferitrin, myricitrin, quercitrin, robinin, rutin, spireoside Spiraeoside, Xanthorhamnin, Amuresin ( Amurensin), Icariin (Icariin), Troxerutin (Troxerutin) and derivatives thereof may include any one selected from the group or a combination thereof.

According to embodiments of the present invention, by impregnating a generally poorly soluble natural or plant-derived sunscreen activator in a hydrophobic liquid polymer medium to high capacity, while stabilizing the sunscreen agent without the addition of solubilizing additives such as pH regulators It is possible to obtain an excellent ultraviolet ray blocking effect. In addition, since a sunscreen active agent of natural or plant origin is used and the hydrophobic liquid polymer medium functions as an oil phase in relation to water, it can be emulsified into O / W type or W / O type, thereby forming various formulations. In addition to providing excellent usability, a stable sunscreen composition can be provided without side effects such as skin diseases.

According to other embodiments of the present invention, a hydrophobic liquid polymer medium that is liquid at room temperature is dissolved in an organic solvent to obtain a sunscreen composition impregnated with a high concentration of the sunscreen activator only by adding and stirring the sunscreen activator. It is possible to provide a method for producing a sunscreen composition that is economical and has excellent light-blocking reproducibility. In addition, there may be provided a method for producing a cosmetic composition that can be obtained by emulsifying the sunscreen composition in O / W type or W / O type to obtain a cosmetic composition of various formulations.

1A and 1B are conceptual diagrams illustrating sunscreen compositions according to embodiments of the present invention.
2 is a conceptual diagram illustrating a sunscreen composition according to another embodiment of the present invention.
3A and 3B are flowcharts illustrating a method of preparing the sunscreen composition according to one embodiment of the present invention.
4 is a graph showing the measurement results of the sunscreen effect of the cream formulation containing the sunscreen composition according to Comparative Example 1 and Examples 1-13.

Hereinafter, exemplary embodiments of the present invention will be described in detail with reference to the accompanying drawings.

The embodiments of the present invention are described in order to more fully explain the present invention to those skilled in the art, and the following embodiments may be modified into various other forms, It is not limited to the embodiment. Rather, these embodiments are provided so that this disclosure will be more faithful and complete, and will fully convey the scope of the invention to those skilled in the art.

In the drawings like reference numerals refer to like elements. In addition, as used herein, the term "and / or" includes any and all combinations of one or more of the listed items.

The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the scope of the invention. Also, although described in the singular, unless the context clearly indicates a singular form, the singular forms may include plural forms. Also, the terms "comprise" and / or "comprising" used herein should be interpreted as referring to the presence of stated shapes, numbers, steps, operations, elements, elements and / And does not exclude the presence or addition of other features, numbers, operations, elements, elements, and / or groups.

In the following, embodiments of the present invention will be described with reference to cross-sectional views schematically showing ideal embodiments of the present invention. In these figures, for example, the size and shape of the members may be exaggerated for convenience and clarity of explanation, and in actual implementation, variations of the illustrated shape may be expected. Accordingly, embodiments of the present invention should not be construed as limited to any particular shape of the regions shown herein. In addition, reference numerals of members in the drawings refer to the same members throughout the drawings.

1A and 1B are conceptual views illustrating sunscreen compositions 100A and 100B according to embodiments of the present invention.

Referring to FIG. 1A, the sunscreen composition 100A includes a hydrophobic liquid polymer medium 10 and a sunscreen activator 20 impregnated in the hydrophobic liquid polymer medium 10. The hydrophobic liquid polymer medium 10 is present in the liquid phase at room temperature, among biologically acceptable non-toxic materials, to facilitate the impregnation of the sunscreen active agent 20, and because of its hydrophobicity, the It can be selected from materials that can be rejected and function like oils in water systems.

Examples of such hydrophobic liquid polymer medium 10 include polyglycerine, polypropylene glycol, hydrogenated polyiosbutene, hydrogenated polydodecene, and derivatives thereof. There may be any one selected from the group consisting of or a combination thereof. These hydrophobic liquid polymer media 10 is a substantially closed space in which the impregnated sunscreen active agent 20 can be stably maintained as shown in FIG. 1 without a regular arrangement unlike liquid crystal, which is another example of a liquid polymer material. The sunscreen active agent 20 may be highly concentrated in the hydrophobic liquid polymer medium 10.

Since the hydrophobicity of the hydrophobic liquid polymer media including the liquid polymer media listed above may have a molecular weight dependency, control of the molecular weight may be required for the design of the hydrophobic liquid polymer medium. For example, polypropylene glycol has hydrophilicity if smaller than this based on molecular weight of about 1000, and hydrophobicity if larger. Similarly, polyglycerin becomes more hydrophobic as its molecular weight increases. Examples of the hydrophobic liquid polymer medium described above are exemplary only, and the present invention is not limited thereto. For example, as the hydrophobic liquid polymer medium, other materials such as copolymers which are liquid at room temperature and have a hydrophobic functional group or a hydrophobic moiety may be applied.

The sunscreen active agent 20 is a light absorbing active material of natural or plant origin. For example, the light absorbing active material may be a phenolic acid compound, a flavonoid compound, or a derivative thereof having safety on the skin and excellent ultraviolet absorbing activity. However, this is exemplary and the present invention is not limited thereto.

The phenolic acid-based compound may be selected from the group consisting of ferulic acid, caffeic acid, coumaric acid, Alpha-cyano-4-hydroxycinnamic acid, Cichoric acid, Cinnamic acid, Chlorogenic acid, Caftaric acid, Coutaric acid, Fertaric acid, Diferulic acid, ), Sinapinic acid, and derivatives thereof. The term " a " Structural formulas (a), (b), and (c) below relate to ferulic acid, caffeic acid, and coumarin acid, which are representative examples of the phenolic acid compounds, respectively, for understanding.

(a)

(b)

(c)

The flavonoid compound is apigenin (apigenin), luteolin (Luteolin), myricetin (myricetin), quercetin (quercetin), camphorol (kaempherol, Tangerine (Tangeritin (4 ', 5, 6, 7, 8-) pentamethoxyflavone)), chrysin (5,7-OH), baicalein (5,6,7-trihydroxyflavone), cutellarein (5,6,7,4'-tetrahydroxyflavone), Wogonin (5,7 -OH, 8 -OCH ₃ ), azeleatin, fisetin, galangin, gosysytin, kaempferide, iso Raminetin, Morin, Natsudaidain, Pachypodol, Rhamnazin, Rhamnetin, Astragalin, Azalein, Azalein, Hyperside, isoquercitin, kaempferitrin, myricitrin, quercitrin, robinin, rutin, spireoside Spiraeoside, Xanthorhamnin, Amuresin ( Amurensin, Icariin, Troxerutin, and derivatives thereof, or any combination thereof, may be included in the following formulas (d), (e) and (f). ) Relates to exemplary apigenin, luteolin and myricetin, respectively.

(d)

(e)

(f)

Referring to FIG. 1B, the sunscreen composition 100B may include two or more kinds of sunscreen active agents 20 different from each other in the hydrophobic liquid polymer medium 10. The embodiment shown in FIG. 1B illustrates a sunscreen composition 100B impregnated with two types of first and second sunscreen activators 20a, 20b. For example, the first sunscreen active agent 20a may be a phenolic acid compound and the second sunscreen active agent 20b may be a flavonoid compound. In other embodiments, the first and second sunscreen active agents 20a, 20b may be different kinds of phenolic acid based compounds or different types of flavonoid based compounds, and other suitable natural or plant derived sun protection not exemplified. It may also be an activator.

The inventors experimentally use two or more different sunscreen activators in the sunscreen composition (100B) than the use of a single type of sunscreen activator to increase the solubility is advantageous for high concentration and the sunscreen effect is improved The ratio of the phenolic acid compound and the flavonoid compound is maximized in the UV blocking coverage spectrum within the range of 4: 1 to 1: 4, and exhibits excellent ultraviolet absorbing ability. This will be described in detail through the following test examples.

The above-mentioned natural or plant-derived light-absorbing active substances absorb ultraviolet rays by converting them into thermal energy through a mechanism known as resonance delocalization, which is common to benzoic acid-based substances. These materials are highly polar molecules and have low stability in the water system, but can be impregnated in the hydrophobic liquid polymer medium so that they can be stably present in the water system by the hydrophobicity provided by the hydrophobic liquid polymer medium. In addition, since the sunscreen compositions 100A and 100B have a hydrophobicity not mixed with water, they may be present in the form of micro droplets in O / W or W / O formulations, and thus, various formulations having improved usability. In addition to making it easy, it also ensures long-term stability in the water system.

The above-mentioned natural light-absorbing active substances are merely exemplary, and the present invention is not limited thereto, and derivatives of the above-mentioned poorly water-soluble natural light-absorbing active substances or other light-absorbing active substances which are physiologically compatible with skin may also be used. It will be appreciated that it can be applied to the present invention.

2 is a conceptual diagram illustrating a sunscreen composition 200 according to another embodiment of the present invention. The description of the members having the same reference numerals as the components shown in FIGS. 1A and 1B among the members of FIG. 2 may refer to the above disclosure as long as there is no contradiction.

Referring to FIG. 2, the sunscreen composition 200 may further include an alcohol compound 30 dissolved in the hydrophobic liquid polymer medium. The alcohol compound 30 lowers the viscosity of the hydrophobic liquid polymer medium 10 to improve the dissolution rate of the sunscreen active agent impregnated in the hydrophobic liquid polymer medium 10 and at the same time impregnate the sunscreen active agents 20a and 20b. Increase the amount. In particular, the alcohol compound 30, as shown in Fig. 2, is effective in improving the amount of impregnation of the phenolic acid compound 20a and stabilizing it.

In some embodiments, the content of alcohol-based compound 30 may be 0.1% to 30% by weight relative to the total weight of the sunscreen composition 200. When the content of the alcohol-based compound (30) is 0.1% by weight or more, the effect of increasing solubility and stability occurs. If the content exceeds 30% by weight, the hydrophobicity of the sunscreen composition 200 is lost, the sunscreen active agent in the formulation Precipitation of (20a, 20b) decreases formulation stability, and the sunscreen effect may be lost.

The sunscreen compositions according to the above embodiments may be formulated into any one of skin, lotion, cream, gel, ointment, paste, powder foundation, serum, emulsion foundation, wax foundation and spray so as to be applicable as a cosmetic composition. Known techniques can be taken into account with regard to their production methods. In addition, the application as the cosmetic composition described above is exemplary, and those skilled in the art, within the scope of the present invention, based on the skin pharmacological effect of the sunscreen active agent, the solubility and stability of the sunscreen composition, the skin, scalp and It should be understood that it may be formulated into pharmaceuticals, foods and beverages that can be consumed. For example, phenolic acid derivatives and flavonoids not only absorb ultraviolet rays, but also have beneficial physiological activities in the skin or body, such as antioxidant, anti-inflammatory and anti-cancer effects. Various products can be formulated to prevent skin aging.

3A and 3B are flowcharts illustrating a method of preparing the sunscreen composition according to one embodiment of the present invention.

Referring to FIG. 3A, a first mixed solution is prepared by adding an organic solvent to a hydrophobic liquid polymer medium (S10). Thereafter, the sunscreen is added to the first mixed solution and stirred to prepare a second mixed solution (S20). The organic solvent may be ethanol, methanol, acetone, tetrahydrofuran, acetonitrile, derivatives thereof, or mixtures thereof.

The organic solvent reduces the viscosity of the hydrophobic liquid polymer medium and dissolves some of the sunscreen agent to be added later to allow the sunscreen agent to dissolve rapidly and in high concentration into the hydrophobic liquid polymer medium. The organic solvents described above are exemplary, and the present invention is not limited thereto, and as such organic solvents, other suitable agents for reducing the viscosity of the hydrophobic liquid polymer medium and facilitating penetration of the sunscreen agent into the hydrophobic liquid polymer medium. Solvents may be used. In another embodiment, a mixed solvent may be used in which two solvents each having excellent solubility for the hydrophobic liquid polymer medium and the sunscreen active agent are mixed.

In some embodiments, the sunscreen active agent may include different types of first and second sunscreen active agents. As described above, the first sunscreen active agent may be, for example, a flavonoid compound, and the second sunscreen active agent may be, for example, a phenolic acid compound. Alternatively, the first and first sunscreen active agents may be different types of flavonoid compounds or different types of phenolic acid compounds.

As such, the process of adding different types of sunscreen activators into the first mixed solution may be performed by dissolving one kind of sunscreen activators sufficiently for high concentration impregnation of the sunscreen activator, and then sequentially dissolving other types of sunscreen activators. It is preferable to make it. This sequential dissolution process may include adding and stirring the first sunscreen activator in the first mixed solution (S21) and a second in the first mixed solution including the first sunscreen activator, as shown in FIG. 3B. It can be achieved by sequentially performing the step (S22) of adding and stirring the sunscreen actives.

Experimentally, when different types of sunscreen active agents are added simultaneously in the first mixed solution or other types of sunscreen agents without completely dissolving one type of sunscreen agent, they are higher in comparison with the above-described sequential dissolution process. It was confirmed that solubility could not be obtained. In addition, the order of the sequential dissolution process may be determined according to the type of the sunscreen activator. For example, in order to impregnate both the flavonoid compound and the phenolic acid compound, it is advantageous for high concentration impregnation to add and stir the flavonoid compound first, and then to dissolve the phenolic acid compound.

In some embodiments, as shown in FIG. 3B, adding and stirring the alcohol compound in the first mixed solution may be further performed (S40). The alcohol compound may include any one or a combination of two or more selected from the group consisting of ethanol, glycerin, propylene glycol, butylene glycol, and dipropylene glycol.

The addition and stirring of the alcoholic compound may be performed prior to the step of adding and stirring the desired sunscreen active agent. For example, as shown in Figure 3b, after adding the flavonoid compound as a first sunscreen activator in the first mixed solution, stirred and completely dissolved (S21), before adding the phenolic acid compound (S22), An alcohol compound compound may be added and stirred in the first mixed solution in which the flavonoid compound is dissolved (S40). In another embodiment, although not shown, the addition and stirring of the alcoholic compound is performed prior to the step (S21) of adding and stirring the first sunscreen activator, or the alcoholic compound is preceded by each of the steps S21 and S22. Can be added and stirred. In this case, the alcohol-based compound may be a different kind, in this case, may be a compound having a good solubility for each of the first and second sunscreen activator.

The alcoholic compound is also impregnated inside the hydrophobic liquid polymer medium to lower the viscosity of the hydrophobic liquid polymer medium and to improve the solubility and dissolution rate of the second sunscreen activator, for example, a phenolic acid compound, to be added later.

Referring again to FIG. 3A together with FIG. 3B, the organic solvent in the second mixed solution may be removed to obtain a sunscreen composition including a sunscreen impregnated in the hydrophobic liquid polymer medium (S30). . Removal of the organic solvent may be performed, for example, by distillation under reduced pressure, vacuum drying, or a combination thereof, but the present invention is not limited thereto.

According to the above-described embodiment, the hydrophobic liquid polymer medium, which is liquid at room temperature, is dissolved in an organic solvent, and then, the UV-blocking composition impregnated with a high concentration of the UV-protecting agent can be obtained simply by adding and stirring the UV-activating agent. There can be provided a method for producing a sunscreen composition having economical and excellent reproducibility. In addition, the sunscreen composition functions as an oil phase in the water system, and may be emulsified in O / W type or W / O type to obtain cosmetic compositions of various formulations.

Hereinafter, specific test examples will be described with respect to the features and advantages of the present invention. The following disclosure is for illustrative purposes only and should not be construed as limiting the invention thereto.

Test Example  1: UV Blocking ability  Measure

Phenolic acid compounds, such as coumarin acid (P), caffeic acid (C), ferulic acid (F) and flavonoid compounds, such as apigenin (A), luteolin (L) and myricetin (M) as sunscreen actives As a comparative example, the UV-blocking ability of octyl methoxycinnamate, a synthetic sunscreen activator generally used as an absorbent of UVB, was evaluated. All samples were diluted to 50 ppm using dimethyl sulfoxide (DMSO) or ethanol as solvent.

Table 1 shows the ultraviolet absorbing ability of the samples consisting of a single sunscreen activator. The absorbance of each wavelength was evaluated using a UV-visible spectrophotometer (spectramax 190 ^R ). After measuring the absorption capacity of each wavelength at 1 nm interval in the wavelength region of 290 ~ 400 nm, the UV blocking ability was measured by comparing the area. The area of 290-320nm area is the blocking ability of UVB, and the area of 320-400nm area is measured and compared by UVA blocking ability.

Sunscreen UVB blocking ability UV A blocking ability Sunscreen UVB blocking ability UV A blocking ability Coumarin acid (P) 61.26 70.26 Apigenin (A) 53.43 92.05 Caffeic Acid (C) 62.62 72.42 Luteolin (L) 37.55 99.63 Ferulic acid (F) 62.52 72.03 Myricetin (M) 35.36 100.33 Octylmethoxy cinnamate 65.83 21.02

Referring to Table 1, it can be seen that when comparing the natural sunscreens with the octylmethoxycinnamate, a synthetic sunscreen activator, an equivalent or better level of sunscreen performance can be obtained even with a natural sunscreen activator.

Table 2 shows a sample formed by mixing caffeic acid (C), which is one of the phenolic acid compounds listed in Table 1, and apigenin (A) and luteolin (L), which are two types of flavonoid compounds (ACL) as sunscreen agents (ACL). ) Shows ultraviolet absorbing ability. The parenthesis is the mixing ratio of each active agent in the sample. The dilution and blocking ability of the sample was measured in the same manner as described in Table 1.

Sunscreen UVB blocking ability UV A blocking ability Sunscreen UVB blocking ability UV A blocking ability ACL (1: 1: 1) 59.79 103.44 ACL (4: 1: 1) 59.06 101.17 ACL (1: 4: 1) 64.49 91.82 ACL (1: 1: 4) 48.17 104.06

Referring to Table 2 together with Table 1, when comparing the phenolic acid-based compounds and flavonoid-based compounds, the blocking ability of UVB B is relatively superior to the phenolic acid compound, and the blocking ability of UVA is more to the flavonoid compound. great. Therefore, according to some embodiments of the present invention, a sunscreen composition having a broad UV blocking coverage spectrum can be obtained by appropriately mixing a phenolic acid compound and a flavonoid compound. In addition, by mixing these different types of compounds, it is possible to obtain a higher solubility compared to a single type of solubility, thereby enhancing the UV blocking ability.

In view of this, ACL (1: 4: 1), which has a high content of caffeic acid, a phenolic acid compound of Table 2, has the highest level of UVB blocking ability and high UV blocking ability of 91.82 to provide UV protection coverage. A broad spectrum sunscreen composition can be obtained. For ACL (1: 1: 1), ACL (4: 1: 1), and ACL (1: 1: 4), where the amount of flavonoid compound is relatively higher than that of phenolic acid compound, Although it can be secured, the blocking ability of UVB is relatively weak. In some embodiments of the present invention, in order to broaden the UV protection coverage spectrum, the mixing weight ratio of the phenolic acid compound and the flavonoid compound may be appropriately selected within the range of 4: 1 to 1: 4.

Example  1-13: Preparation of a phenolic acid compound or a flavonoid compound containing sunscreen composition

Select one or more of the hydrophobic liquid polymer media, dissolve them in ethanol which is an organic solvent to form a first mixed solution, and then sequentially add the flavonoid compounds shown in Table 1 to the first mixed solution and It was stirred to dissolve to form a second mixed solution. Thereafter, one or more kinds of alcohol compounds were selected and added to the second mixed solution, followed by stirring. Then, the phenolic acid compound was sequentially added and stirred to dissolve. At this time, stirring was performed at 45 degreeC.

In order to add two types of sunscreen actives as described above, once the first sunscreen is completely dissolved and transparent, then all the sunscreen actives are transparently dissolved in a sequential dissolution mode where the next second sunscreen is added and stirred. . Thereafter, the ethanol was removed in a vacuum dryer for 12 hours to obtain a transparent liquid sunscreen composition containing a phenolic acid compound and a flavonoid compound. Table 3 shows the component ratios of the sunscreen compositions comprising two or more sunscreen active agents thus obtained.

Furtherance Example (number is by weight) One 2 3 4 5 6 7 8 Flavonoids Apigenin One One One One One One One One Luteolin 2.5 2.5 2.5 2.5 2.5 2.5 2.5 2.5 Myricetin 3 3 3 3 3 3 3 3 Phenolic Acid System Coumarin acid 4.5 4.5 4.5 4.5 4.5 4.5 4.5 4.5 Caffeic acid 6 6 6 6 6 6 6 6 Peru ricans 8 8 8 8 8 8 8 8 synthesis 25 25 25 25 25 25 25 25 Hydrophobic Liquid Polymer Polyglycerin 50 63 30 Polypropylene glycol 50 63 33 30 Polyisobutene 50 63 33 Alcohol glycerin 25 12 6 Propylene glycol 25 12 6 6 Butylene glycol 25 12 6 sum 100 100 100 100 100 100 100 100 Furtherance Example (number is by weight) 9 10 11 12 13 Flavonoids Apigenin One One One One One Luteolin 2.5 2.5 2 2 2 Myricetin 3 3 3 3 3 Phenolic Acid System Coumarin acid 4.5 4.5 2 2 2 Caffeic acid 6 6 3 3 3 Peru ricans 8 8 4 4 4 synthesis 25 25 15 15 15 Hydrophobic Liquid Polymer Polyglycerin 30 20 84 Polypropylene glycol 20 84 Polyisobutene 33 20 84 Alcohol glycerin 6 5 One Propylene glycol 5 One Butylene glycol 6 5 One sum 100 100 100 100 100

Comparative Example  One: TEA ( triethanolamine ) With added 1,3 Butylene glycol  Mixed solution

For comparison test with the sunscreen composition according to Examples 1 to 13, a solution of a phenolic acid compound and a flavonoid compound of the same content dissolved in a 1,3 butylene glycol mixed solution added with TEA (triethanolamine) as a pH regulator Was used. In the case of the phenolic acid compound or the flavonoid compound, the solution of Comparative Example 1 in which the same content of the sunscreen activator is dissolved can be obtained by dissolving well in the 1,3 butylene glycol mixed solution.

Test Example  2: Stability test

The cream formulation was used to test the stability of the sunscreen compositions according to the examples described above. At this time, the cream formulations were completely dissolved at 70 ° C. after the A and B phases were completely dissolved, respectively, according to the ingredients and contents shown in Table 4, and then uniformly dispersed. The mixture was then cooled to 40 ° C. and slowly cooled to room temperature to complete the sunscreen cream formulation.

Phase separation Raw material name INCI name Content (% by weight) A Caprylic / capric triglyceride Caprylic / capric triglyceride 3 STEARIC ACID STEARIC ACID 0.7 ARCEL 165 PEG-100 stearate One GMS-205 Glyceryl Stearate 0.45 LANETTE-O cetearyl alcohol 0.6 MONTANOV 202 arachidyl alcohol One TEGO CARE 450 Polyglyceryl-3 Methylglucose Distearate 0.5 Example (1-13) or Comparative Example 1 - 30 B Purified water Purified water 60 EDTA-3Na EDTA-3Na 0.05 KELTROL-F xanthan gum 0.1 VEEGUM ULTRA magnesium aluminum silicate 0.3 Phenoxyethanol Phenoxyethanol 0.5 D-PANTHENOL D-PANTHENOL One SILICA SILICA 0.5 KOH (85%) KOH (85%) 0.3 sum 100

For stability testing, the sunscreen compositions of Comparative Example 1 and Examples 1-13 were added to 7.5% by weight of the cream formulation of Table 4. The stability was then assessed by observing the time course changes of phase separation and discoloration of the formulation, while stored at room temperature and 45 ° C. for 4 weeks. Discoloration and phase separation were compared visually. The degree of discoloration was evaluated by classifying into 6 grades. Discoloration evaluation criteria were classified into no change (0), very little change (1), little change (2), little change (3), severe change (4) and extremely change (5). Phase separation was determined with and without. The stability evaluation results are shown in Table 5.

division Sunscreen cream formulation Room temperature 45 ° C Comparative Example 1 Phase separation Formulation Bundle Formulation Bundle discoloration Initial color dark Initial color dark Example 1 Phase separation radish radish discoloration 0 One Example 2 Phase separation radish radish discoloration 0 One Example 3 Phase separation radish radish discoloration 0 One Example 4 Phase separation radish radish discoloration 0 One Example 5 Phase separation radish radish discoloration 0 One Example 6 Phase separation radish radish discoloration 0 One Example 7 Phase separation radish radish discoloration 0 One Example 8 Phase separation radish radish discoloration 0 One Example 9 Phase separation radish radish discoloration 0 One Example 10 Phase separation radish radish discoloration 0 One Example
11 Phase separation radish radish discoloration 0 One Example
12 Phase separation radish radish discoloration 0 One Example
13 Phase separation radish radish discoloration 0 One

Referring to Table 5, it can be seen that the sunscreen composition of Examples 1-13 has a significant improvement in formulation stability due to little phase separation and discoloration compared to Comparative Example 1. In the case of Comparative Example 1, not only the initial color has a dark tan, but also agglomeration occurs, which makes it impossible to commercialize.

Test Example  3: UV protection effect test

UV protection effect was tested using the cream formulations containing the sunscreen composition of Comparative Example 1 and Examples 1 to 13 prepared in Test Example 2 above. In the measurement method, 2 mg / cm ² of the sample was applied to a transpore tape (3M), dried for 20 minutes, and the ultraviolet ray blocking effect was measured using an SPF-290S analyzer (available from Optometrics Corp.). 4 is a graph showing the measurement results of the sunscreen effect of the cream formulation containing the sunscreen composition according to Comparative Example 1 and Examples 1-13.

Referring to Figure 4, the cream formulations of Examples 1 to 13 all have a SPF value as high as five times higher than the cream formulation of Comparative Example 1. Regarding this difference in SPF value, in Comparative Example 1, it is presumed that the phenolic acid-based compounds and the flavonoid-based compounds that were dissolved in the preparation of the cream formulation were recrystallized during the preparation of the formulation, so that these compounds lost the sunscreen efficacy. On the other hand, in the cream formulations of Examples 1 to 13, since the sunscreen activator can be stably present at a high concentration by the hydrophobic liquid polymer medium and the added alcohol compound, excellent sunscreen effect can be obtained.

It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the spirit or scope of the invention as defined in the appended claims. It will be clear to those who have knowledge.

Claims (21)

delete delete delete delete delete delete delete delete delete delete A first mixed solution is prepared by adding an organic solvent to a hydrophobic liquid polymer medium, which is any one or a combination thereof, selected from the group consisting of polyglycerol, polypropylene glycol, hydrogenated polyisobutene, and hydrogenated polydodecene. Doing;
Preparing a second mixed solution by adding and stirring a sunscreen activator in the first mixed solution; And
Removing the organic solvent in the second mixed solution to obtain a sunscreen composition comprising a sunscreen immersion agent in the hydrophobic liquid polymer medium. The method of claim 11,
The organic solvent is ethanol (Ethanol), methanol (Methanol), acetone (Acetone), tetrahydrofuran (THF: Tetrahydrofuran), acetonitrile, or a mixture thereof. The method of claim 11,
The sunscreen active agent comprises a first sunscreen activator and a second sunscreen activator different from the first sunscreen activator,
The preparing of the second mixed solution may include sequentially dissolving the first sunscreen activator and the second sunscreen activator in the first mixed solution. The method of claim 11,
And adding and stirring an alcohol compound in the first mixed solution before adding the sunscreen active agent. 15. The method of claim 14,
The content of the alcohol-based compound is a method for producing a sunscreen composition, characterized in that 0.1 to 30% by weight relative to the total weight of the sunscreen composition. 15. The method of claim 14,
The alcohol-based compound is a method for producing a sunscreen composition comprising any one or a combination of two or more selected from the group consisting of ethanol, glycerin, propylene glycol, butylene glycol, and dipropylene glycol . The method of claim 11,
Removing the organic solvent is carried out by vacuum distillation, vacuum drying, or a combination thereof. The method of claim 11,
Method for producing a sunscreen composition, characterized in that the weight ratio of the sunscreen active agent to the hydrophobic liquid polymer medium is 1/9 to 1/2. The method of claim 11,
The sunscreen active agent is a method for producing a sunscreen composition, characterized in that it comprises any one or a combination of phenolic compounds and flavonoid compounds. The method of claim 19,
The phenolic acid compound is ferulic acid (ferulic acid), caffeic acid (caffeic acid), coumaric acid (coumaric acid), alpha-cyanohydroxyhydroxynamic acid (Alpha-cyano-4-hydroxycinnamic acid), chicory acid (Cichoric acid) acid, Cinnamic acid, Chlorogenic acid, Caftaric acid, Coutaric acid, Fertaric acid, Deferulic acid And, and a method for producing a sunscreen composition characterized in that it comprises any one or a combination thereof selected from the group consisting of Sinapinic acid (Sinapinic acid). The method of claim 19,
The flavonoid-based compound is quercetin (quercetin), camphorol (kaempherol, apigenin), luteolin (Luteolin), myricetin (myricetin), Tangerine (Tangeritin (4 ', 5, 6, 7, 8-) pentamethoxyflavone)), chrysin (5,7-OH), baicalein (5,6,7-trihydroxyflavone), cutellarein (5,6,7,4'-tetrahydroxyflavone), Wogonin (5,7 -OH, 8 -OCH ₃ ), azeleatin, fisetin, galangin, gosysytin, kaempferide, iso Raminetin, Morin, Natsudaidain, Pachypodol, Rhamnazin, Rhamnetin, Astragalin, Azalein, Azalein, Hyperside, isoquercitin, kaempferitrin, myricitrin, quercitrin, robinin, rutin, spireoside Spiraeoside, Xanthorhamnin, Amuresin ( Amurensin), Icariin (Icariin), and a method for producing a sunscreen composition comprising any one or a combination thereof selected from the group consisting of Troxerutin (Troxerutin).

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