JPH1025219A - Preparation for external use for skin - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a stable and safe preparation for external use for skin capable of effectively protecting the skin from damages due to light or oxidative stress and treating or preventing dermatopathy and aging symptoms of the skin caused thereby. SOLUTION: This preparation for external use for skin comprises one or more of hydroxylated xanthone-benzophenone dimers. Xanthone-1,6-diol and xanthone-3,6-diol are especially preferred as the hydroxylated xanthone. 2- Hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and its salt, dihydroxydimethoxybenzophenone, dihydroxydimethoxybenzophenone-sulfonic acid and its salt, 2,4- dihydroxybenzophenone and tetrahydroxybenzophenone are cited as the preferred benzophenone.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an external preparation for skin which can effectively protect the skin from damage caused by light and oxidative stress, and treat or prevent skin diseases and skin aging caused by these. . More specifically, the present invention relates to an external preparation for skin comprising one or more hydroxylated xanthone / benzophenone dimers.

[0002]

2. Description of the Related Art Excessive exposure to ultraviolet light and oxidative stress caused by ultraviolet light and endogenous oxygen cause a series of inflammatory reactions starting from the development of erythema in the skin, and further destruction of collagen fibers in subcutaneous tissue. The aging of the skin is promoted by the occurrence of fine wrinkles, pigmentation such as spots and freckles, and in the worst case, a tumor may develop. In recent years, the harmfulness of ultraviolet rays and oxidative stress to the skin has been generally recognized, and the demand for external preparations and cosmetics for the purpose of preventing ultraviolet rays and eliminating active oxygen species has been increasing.

In order to prevent ultraviolet rays, an ultraviolet absorber or an inorganic coating agent such as zinc oxide or titanium oxide which has a shielding effect by irregularly reflecting ultraviolet rays is blended. Examples of the ultraviolet absorber include paraaminobenzoic acid (PABA) such as 2-ethylhexyl paradimethylaminobenzoate, cinnamate esters such as 2-ethylhexyl paramethoxycinnamate, and 4-t-
Various compounds such as dibenzoylmethanes such as butyl-4'-methoxydibenzoylmethane and benzophenones such as 2-hydroxy-4-methoxybenzophenone are used. There have been reports of the occurrence of light contact dermatitis, sensitization or cumulative irritation. In addition, a skin external preparation for the purpose of preventing ultraviolet rays is required to have both water resistance to water and sweat and oil resistance to sebum and the like. there were.

[0004] On the other hand, inorganic coating agents such as zinc oxide and titanium oxide having an irregular reflection function of ultraviolet rays must be incorporated in a considerable amount in order to obtain sufficient coating properties, and the coating power is too high because the hiding power is too high. When unnatural whiteness occurs,
There has been a problem that the makeup lasts poorly, such as occurrence of powder floating.

[0005] Vitamin Es, glutathione, superoxide dismutase, etc. are used as active oxygen species scavengers. In addition, plant extracts having an active oxygen species scavenging action have been reported. However, many of the above-mentioned components which have been conventionally used are unstable to light, heat, and the like, and their actions and effects are insufficient. It often required a considerable amount. Furthermore, it has been difficult to secure a certain quality, especially for those derived from natural products such as plant extracts.

[0006]

SUMMARY OF THE INVENTION The present invention has been made to solve the above-mentioned problems, has a very excellent ultraviolet ray preventing effect and an active oxygen species erasing effect, and is effective in preventing damage due to light or oxidative stress. An object of the present invention is to provide a skin external preparation that can protect the skin, treat or prevent skin diseases and skin aging symptoms caused by the skin, and is excellent in stability and safety.

[0007]

In order to solve the above-mentioned problems, various studies have been made. As a result, a dimer formed from hydroxylated xanthones and benzophenones has excellent ultraviolet absorbing ability and elimination of reactive oxygen species. It was found that when this was incorporated into an external preparation for skin, an excellent effect was obtained at a very low concentration, and that the formulation stability and the safety on the skin were also excellent.

That is, in the present invention, one or more kinds of hydroxylated xanthone / benzophenone dimers are selected and contained in an external preparation base. Such hydroxylated xanthone-benzophenone dimer is known to be contained in Hypericum plants and the like. Extracts of these plants can be obtained by, for example, the method of Iinuma et al. (Abstracts of the 116th Annual Meeting of the Pharmaceutical Society of Japan, 116th Annual Meeting). 2 page 177)
It can be isolated and purified by silica gel column chromatography, Sephadex LH-20 column chromatography and recrystallization. Furthermore, the xanthone benzophenone dimer isolated and purified as described above can be chemically modified to further enhance the activity.

Further, it can also be obtained by using xanthone or a xanthone derivative obtained from a plant or a microorganism as a starting material, by performing a radical reaction with a diazonium salt and an alkali, to bond with a benzophenone, and hydroxylating the compound.

The hydroxylated xanthone constituting the hydroxylated xanthone / benzophenone dimer is preferably xanthone-1,6-diols and xanthone-3, in view of ultraviolet ray preventing ability, elimination of reactive oxygen species and safety. 6-diols are preferred.

On the other hand, as benzophenones, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and salts thereof, dihydroxydimethoxybenzophenone, dihydroxy It is preferred to select from dimethoxybenzophenone-sulfonic acid and its salts, 2,4-dihydroxybenzophenone and tetrahydroxybenzophenone.

Examples of the above-mentioned hydroxylated xanthone-benzophenone dimer include xanthone-1,6-diol-2-hydroxy-4-methoxybenzophenone dimer as shown in Chemical Formula 1 and xanthone as shown in Chemical Formula 2 -
3,6-diol / 2-hydroxy-4-methoxybenzophenone dimer and the like. In the present invention, the hydroxylated xanthone-benzophenone dimer was used in the form of a mixture of several isomers obtained after the reaction.

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[0013] Formulation in the external preparation base may be carried out by mixing a hydroxylated xanthone / benzophenone dimer with lower alcohols such as ethanol, propanol and isopropanol;
Since it is soluble in polyhydric alcohols such as glycerin, propylene glycol, dipropylene glycol and 1,3-butylene glycol, it is preferable to dissolve in these. Moreover, you may mix | blend and make into microencapsulation or a liposome. The blending amount varies depending on the base material and the degree of the expected effect, but is 0.01 to 10.0.
A suitable amount is about weight%.

In the present invention, general external preparations such as other active oxygen species scavengers, anti-inflammatory agents, whitening agents, bactericides, oils, humectants, ultraviolet absorbers, fragrances, preservatives, etc. In addition, a raw material for cosmetics can be contained.

[0015]

The external preparation for skin according to the present invention has an excellent ultraviolet ray preventing ability and an active oxygen species elimination action, so that it protects the skin from damage caused by light and oxidative stress, and causes skin diseases and aging of the skin. It is effective for the improvement, treatment and prevention of symptoms and pigmentation symptoms. Further, when used for hair, damage to the hair due to ultraviolet rays or the like can be improved and prevented, and healthy and beautiful hair can be maintained.

The hydroxylated xanthone-benzophenone dimer contained as an active ingredient in the present invention has good stability, low cytotoxicity and a sufficient effect at a low concentration. It can satisfactorily improve safety problems such as skin irritation and skin sensitization and poor water resistance and oil resistance, which are observed in the preparation. Furthermore, since it shows good absorption in both long-wavelength ultraviolet (UVA) and mid-wavelength ultraviolet (UVB), it is possible to efficiently prevent both erythema and delayed blackening due to ultraviolet light.

[0017]

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a lotion, an emulsion,
It can be provided as a skin external preparation in the form of a gel, cream, ointment or the like. Further, cosmetics for preventing skin aging such as lotions, emulsions and creams, or sunscreen cosmetics in the form of makeup base lotions, makeup base creams, foundations in the form of liquids, creams, ointments or powders. , Shampoos, rinses, hair treatments and the like, and hair cosmetics such as hand creams, leg creams and body lotions.

[0018]

EXAMPLES The present invention will be described in more detail with reference to Examples.

Example 1 Skin lotion (1) Ethanol 10.0 (% by weight) (2) Hydroxyethyl cellulose 1.0 (3) Xanthone-1,6-diol.2-hydroxy-4-10. 0 Methoxybenzophenone dimer-encapsulated liposome (encapsulation rate: 3.0% by weight) (4) Purified water 79.0 Production method: (1) and (2) are dissolved in (4), and then (3) is added. And evenly disperse.

Example 2 Emulsion for skin (1) Stearic acid 0.2 (% by weight) (2) Cetanol 1.5 (3) Vaseline 3.0 (4) Liquid paraffin 7.0 (5) Polyoxy Ethylene (10E.O.) monooleic acid 1.5 ester (6) Tocopherol acetate 5.0 (7) Xanthone-1,6-diol 2-hydroxy-4-2.5 methoxybenzophenone-5-sulfonic acid diester (8) Glycerin 5.0 (9) Methyl parahydroxybenzoate 0.1 (10) Triethanolamine 1.0 (11) Purified water 73.2 Production method: The oil phase components of (1) to (7) Mix and dissolve uniformly by heating and keep at 70 ° C. On the other hand, the aqueous phase components (8) to (11) are mixed and heated to be uniform, and the temperature is set to 70 ° C. The oil phase component is gradually added to the water phase component with stirring, emulsified, and cooled.

Example 3 Skin Gel (1) Dipropylene glycol 10.0 (% by weight) (2) Carboxyvinyl polymer 0.5 (3) Potassium hydroxide 0.1 (4) Methyl paraoxybenzoate 0.1 (5) Xanthone-1,6-diol 2-hydroxy-4-2.0 sodium methoxybenzophenone-5-sulfonate dimer (6) Purified water 83.3 (7) Ascorbic acid phosphate Magnesium salt 4.0 Production method: After (2) is uniformly dissolved in (6), (1) is (4), (5)
Is dissolved and added, then (3) is added to thicken, (7)
Add and mix.

Example 4 Skin Cream (1) Beeswax 6.0 (% by weight) (2) Cetanol 5.0 (3) Reduced Lanolin 8.0 (4) Squalane 27.5 (5) Glyceryl fatty acid ester 4.0 (6) Lipophilic glyceryl monostearate 2.0 (7) Polyoxyethylene (20E.O.) sorbitan 5.0 Monolaurate (8) Xanthone-1,6-diol · 2,4 -Dihydroxy 1.5 benzophenone dimer (9) Xanthone-3,6-diol ・ 2-hydroxy-4-1.5 methoxybenzophenone dimer (10) Propylene glycol 5.0 (11) Methyl paraoxybenzoate 0 1.1 (12) Purified water 33.4 (13) Retinol palmitate 1.0 Production method: Mix and dissolve the oil phase components (1) to (9) and heat to 75 ° C. On the other hand, the aqueous phase components (10) to (12) are mixed and dissolved and heated to 75 ° C. Next, the oil phase component is added to the water phase component and pre-emulsified, then uniformly emulsified by a homomixer, and after cooling, (13) is added and mixed at 40 ° C.

Example 5 Oil-in-water emulsion ointment for skin (1) White petrolatum 25.0 (% by weight) (2) Stearyl alcohol 25.0 (3) Sodium lauryl sulfate 1.0 (4) Glycerin 10 0.0 (5) Methyl parahydroxybenzoate 0.1 (6) Xanthone-1,6-diol 2-hydroxy-4-2.0 Sodium methoxybenzophenone-5-sulfonic acid dimer (7) Xanthone-3, 6-diol 2-hydroxy-4-2.0 sodium methoxybenzophenone-5-sulfonic acid dimer (8) Purified water 34.4 (9) Retinoic acid 0.5 Production method: (1) to (3) Mix and dissolve the oil phase components to make them uniform,
Heat to 75 ° C. On the other hand, the aqueous phase components (4) to (8) are mixed,
The mixture is dissolved and heated to 75 ° C., and the oil phase component is added to this to emulsify. After cooling, (9) is added and mixed at 40 ° C.

Example 6 Anti-aging lotion (1) Ethanol 10.0 (% by weight) (2) 1,3-butylene glycol 5.0 (3) Xanthon-3,6-diol 2-hydroxy -4- 1.0 Methoxybenzophenone dimer (4) Fragrance 0.1 (5) Purified water 83.9 Production method: Dissolve (3) in (1) and (5) together with (2) and (4) And uniformly mix and dissolve.

[Example 7] Emollient cream (water-in-oil type) (1) Liquid paraffin 30.0 (% by weight) (2) Microcrystalline wax 2.0 (3) Vaseline 5.0 (4) Diglyceryl geo Oleic acid ester 5.0 (5) sodium L-glutamate 1.6 (6) L-serine 0.4 (7) propylene glycol 3.0 (8) methyl parahydroxybenzoate 0.1 (9) xanthon-3, 6-diol / dihydroxy 1.5 sodium dimethoxybenzophenone-sulfonate dimer (10) Purified water 51.3 (11) Fragrance 0.1 Production method: dissolve (5) and (6) in part of (10) To 50 ° C and 5
Add slowly to (4) heated to 0 ° C. with stirring. This was previously mixed and uniformly dispersed in (1) to (3), which were heated and dissolved at 70 ° C., and (7), (8), and (9) were dissolved in the remainder of (10) and heated to 70 ° C. The heated mixture is added with stirring and emulsified by a homomixer. After cooling, add (11) at 40 ° C. and mix.

Example 8 Makeup Base Cream for Sunscreen (1) Stearic acid 12.0 (% by weight) (2) Cetanol 2.0 (3) Glyceryl tri-2-ethylhexanoate 2.5 (4 ) Self-emulsifying glyceryl monostearate 2.0 (5) Xanthone-1,6-diol / tetrahydroxy 3.5 Benzophenone dimer (6) Propylene glycol 10.0 (7) Potassium hydroxide 0.3 ( 8) Methyl paraoxybenzoate 0.1 (9) Purified water 66.0 (10) Titanium dioxide 1.0 (11) Bengala 0.1 (12) Yellow iron oxide 0.4 (13) Perfume 0.1 Production method: The oil phase components (1) to (5) are mixed and heated to 75 ° C. to make them uniform. On the other hand, the aqueous phase components of (6) to (9) were mixed and
The mixture is heated and dissolved to make the mixture uniform, and the pigments (10) to (12) are added thereto, and the mixture is uniformly dispersed with a homomixer. The oil phase component is added to the aqueous phase component, emulsified by a homomixer, cooled, and (13) is added and mixed at 40 ° C.

[Example 9] Liquid foundation for sunscreen (1) stearic acid 2.00 (wt%) (2) squalane 5.00 (3) octyldodecyl myristate 5.00 (4) cetanol 1.00 ( 5) Polyglyceryl monoisopalmitate 9.00 (6) Xanthone-1,4,5-triol 2-hydroxy 4.00-4-methoxybenzophenone dimer (7) 1,3-butylene glycol 6.00 (8) Potassium hydroxide 0.10 (9) Methyl parahydroxybenzoate 0.10 (10) Purified water 49.55 (11) Titanium oxide 9.00 (12) Talc 7.40 (13) Bengala 0.50 ( 14) Yellow iron oxide 1.10 (15) Black iron oxide 0.10 (16) Fragrance 0.15 Production method: Mix oil phase components of (1) to (6) and heat to 75 ° C to make uniform . On the other hand, the aqueous phase components (7) to (10) were mixed, and 75
The mixture was heated to a temperature of 0 ° C. and dissolved to make the mixture uniform. The pigments (11) to (15) were added thereto, and the mixture was uniformly dispersed with a homomixer. The oil phase component is added to the aqueous phase component, emulsified by a homomixer, cooled, and (16) is added and mixed at 40 ° C.

[Example 10] Powder foundation for sunscreen (1) Bengala 3.0 (% by weight) (2) Yellow iron oxide 2.5 (3) Black iron oxide 0.5 (4) Nylon powder 10.0 (5) Titanium oxide 10.0 (6) Mica 17.0 (7) Talc 40.8 (8) Liquid paraffin 5.0 (9) Octyldodecyl myristate 2.5 (10) Vaseline 2.5 (11) Xanthone-1,3,6,8-tetraol.2-6.0 hydroxy-4-methoxybenzophenone dimer (12) Methyl paraoxybenzoate 0.1 (13) Fragrance 0.1 Production method: (1) ~ The pigment component (7) is mixed and pulverized through a pulverizer. This is transferred to a high-speed blender, and (8) to (13) are mixed and added, and mixed uniformly. This is processed by a pulverizer, passed through a sieve to make the particle size uniform, and then compression molded into a metal plate.

Example 11 Shampoo (1) Sodium alkyl ether sulfate 18.000 (% by weight) (2) Coconut oil fatty acid diethanolamide 2.000 (3) Propylene glycol 2.000 (4) Xanthon-1,6 -Diol / dihydroxy 3.000 dimethoxybenzophenone-sulfonic acid sodium dimer (5) Yellow No. 4 0.001 (6) Fragrance 0.200 (7) Purified water 74.799 Production method: (1) to (6) Add sequentially to (7) to make uniform.

Example 12 Hair rinse (1) Cetanol 3.000 (% by weight) (2) Stearyl trimethylammonium chloride 0.700 (3) Xanthon-3,6-diol.2-hydroxy-4-3. 000 methoxybenzophenone-5-sulfonic acid dimer (4) glycerin 3.000 (5) N-cocoyl-L-arginine ethyl ester 0.100 -DL-pyrrolidone carboxylate (6) Green No. 3 0.002 ( 7) Purified water 90.098 (8) Fragrance 0.100 Production method: Mix and dissolve the aqueous phase components (4) to (7) and heat to 70 ° C. On the other hand, the oil phase components (1) to (3) were mixed and dissolved,
Heat to 0 ° C. The oil phase is gradually added to the aqueous phase while stirring, and pre-emulsified, made uniform by a homomixer, cooled, and (8) was added and mixed at 40 ° C.

Example 13 Liquid Body Cleanser (1) N-lauroyl-L-glutamic acid triethanol 20.0 (wt%) amine (30.0 wt% aqueous solution) (2) N-lauryl methyl taurine sodium 10 0.0 (30.0% by weight aqueous solution) (3) Triethanolamine laurate 10.0 (4) Triethanolamine myristate 10.0 (5) Lauryl imidazolinium betaine 5.0 (6) Lauroyl diethanolamide 5 0.0 (7) Propylene glycol 7.0 (8) Xanthone-1,6-diol 2-hydroxy-4-1.5 sodium methoxybenzophenone-5-sulfonic acid dimer xanthon-3,6-diol 2-Hydroxy-4-methoxybenzophenone-5-sulfonic acid sodium dimer mixture (9) Purified water 31.4 (10) Fragrance 0.1 Production method: Each component of (1) to (10) is added and mixed sequentially. And uniform I do.

Of the above Examples, Examples 1 to 5 were evaluated for their effects of preventing aging and improving skin roughness. At that time, in each example, hydroxylated xanthone
Comparative Examples 1 to 5 in which the benzophenone dimer was replaced with benzophenones each corresponding to a component of the dimer
And evaluated similarly.

First, the effect of preventing skin aging was evaluated by evaluating the effect of suppressing the occurrence of wrinkles in hairless mice. In the evaluation, five hairless mice were set as one group,
For each group, Example and Comparative Example were applied to the back once a day, respectively, and 1 J / cm ² / week long wavelength ultraviolet (UVA)
Was irradiated for 50 weeks, the occurrence of wrinkles on the back skin of the hairless mouse was observed, and scored according to the criteria shown in Table 1. At this time, a group to which only purified water was applied was used as a control. The results are shown in Table 2 by calculating the average value of each group and showing the relationship with the number of UVA irradiation days.

[Table 1]

Next, the effect of improving skin roughness was evaluated by using 20 female panelists with remarkable skin roughness symptoms as a group, and using each of the Examples and Comparative Examples twice a day in each group continuously for one month in a blind. After one month, the symptoms of the skin were observed and compared with before the start of use. The skin roughness symptoms were scored according to the criteria shown in Table 3 and the average value of 20 persons was calculated.

[Table 3]

[0035]

[Table 2] In Table 2, occurrence of deep wrinkles was observed in most of the hairless mice in the control group after 50 weeks. However, in the group to which the examples of the present invention were applied, the occurrence of wrinkles was significantly suppressed in all cases. After 50 weeks, only slight wrinkles or slight wrinkles were observed. In particular, in the group coated with Example 5 having a large content of hydroxylated xanthone-benzophenone dimer, a good wrinkle preventing effect was recognized. On the other hand, in the comparative example application group containing only benzophenones alone, although the tendency of suppressing the occurrence of wrinkles is observed in any case, the degree of the suppression is extremely small, and tocopherol acetate which is a vitamin having an anti-aging effect is very small. Also in Comparative Example 2 to Comparative Example 5 application group containing the same, the occurrence of wrinkles was not sufficiently suppressed.

[0036]

[Table 4] Next, Table 4 shows that in the group using the examples of the present invention, favorable improvement of the rough skin symptom was observed in all the groups, and it was shown that the skin condition was recovered to almost satisfactory. In contrast, only a slight improvement in skin roughness was observed in the group using Comparative Example 1, and the recovery of the skin condition was insufficient even in the groups using Comparative Examples 2 to 5.

The sunscreen cosmetics of Examples 8 to 10 were evaluated for the effect of preventing sunburn. The evaluation of the sun protection effect was performed by using Sun Protection Fa.
ctor (SPF) and UVA protection index. Also in this case, in each of Examples, the hydroxylated xanthone / benzophenone dimer was replaced with the corresponding benzophenones, respectively, as Comparative Examples 8 to 10, and the evaluation was performed simultaneously.

The SPF was determined by using a xenon arc solar simulator as a light source, determining the minimum erythema amount (MED) of the uncoated portion of the sample in advance using 20 adult males of skin types I to III as subjects, and then calculating the expected SPF of the sample. Irradiation over the value is performed in five steps at a common ratio of 1.3, the MED of the sample-coated part is obtained, and the SPF is calculated by dividing the value of the sample-coated part by the value of the sample-uncoated part, and the average value of each subject Is represented by

On the other hand, the UVA protection index was determined in advance by using a xenon arc solar simulator as a light source and measuring the minimum immediate blackening amount (MIPD) of the uncoated portion of the sample with 20 adult males of skin types III and IV as subjects. After that, the irradiation of the sample with the expected defense index value or more was 1.2
The MIPD of the sample-applied portion was determined in 5 steps, and the defense index was calculated by dividing the value of the sample-applied portion by the value of the sample-unapplied portion, and represented by the average value of each subject.

Further, after each sample was applied, the temperature was changed to 30 ° C.
SPF after exercising for 2 hours in an environment of 75 ° C and 75% humidity
The values and the UVA protection index were determined in the same manner as described above, and the results are shown in Table 5.

[0041]

[Table 5] As is clear from Table 5, the examples of the present invention all show significantly higher SPF values and UVA protection indexes than the respective comparative examples. Then, even after exercising for 2 hours in a hot and humid environment, all of the examples of the present invention maintained good SPF value and UVA protection index. On the other hand, in the comparative example, the SPF value and the UVA protection index after exercise for 2 hours were decreased, and particularly, in the cream and emulsion liquid forms of Comparative Examples 8 and 9, a marked decrease was observed.

Examples 8 to 10 and Comparative Example 8
About Comparative Example 10, skin irritation was evaluated. The skin irritation was evaluated by performing a 48-hour occlusion patch test on the back skin of 30 adult males as panelists, and the results were determined according to the criteria shown in Table 6, and the average value of the skin irritation index of 30 individuals was calculated. . The results are shown in Table 7.

[Table 6]

[0043]

[Table 7] In Table 7, the examples of the present invention were all 0.07 to
The skin irritation index was very low at 0.13, and no problematic contact skin irritation and skin sensitization were observed. On the other hand, in each comparative example, some skin irritation was observed.

Subsequently, with respect to Examples 11 and 12, the protective effect of the hair against damage by ultraviolet rays was evaluated. At that time, Comparative Examples 11 and 12 were obtained by replacing the hydroxylated xanthone / benzophenone dimer with the corresponding benzophenone in each Example. An undamaged hair bundle was immersed in each sample solution for 5 minutes, washed lightly with water, dried, and 174 using a sun tester.
After irradiation with kJ, 290 to 390 nm ultraviolet rays for 4 hours, the state of the hair was observed with a scanning electron microscope manufactured by Hitachi. The condition of the hair was scored according to the criteria shown in Table 8. Evaluation was performed using three types of hair bundles for the case where each sample was immersed and the case where only water washing was performed and ultraviolet irradiation was performed. Table 9 shows the average value of the evaluation points for each hair bundle.

[Table 8]

[0045]

[Table 9] As can be seen from Table 9, the irradiation of the ultraviolet rays showed significant cuticle detachment overall in the control hair bundle, but a slight cuticle detachment was observed when treated according to the example of the present invention. And showed that the hair was effectively protected from damage by UV radiation. On the other hand, when the treatment was carried out according to the comparative example, the protective effect against damage by ultraviolet rays was small and insufficient.

[0046]

As described in detail above, according to the present invention, the skin can be effectively protected from damage caused by light or oxidative stress,
It was possible to treat or prevent skin diseases and skin aging symptoms caused by these, and to obtain a skin external preparation excellent in stability and safety. In addition, a cosmetic having a good ultraviolet protection effect and capable of favorably preventing inflammation and blackening due to sunburn and damage to hair by ultraviolet rays could be obtained.

Claims (4)

[Claims] 1. An external preparation for skin, comprising one or more hydroxylated xanthone-benzophenone dimers. 2. The method according to claim 1, wherein the hydroxylated xanthone-benzophenone dimer is a dimer of xanthone-1,6-diol or xanthone-3,6-diol, or a mixture thereof and benzophenones. The topical skin preparation according to the above. 3. The benzophenones constituting the hydroxylated xanthone benzophenone dimer are 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and salts thereof, dihydroxydimethoxybenzophenone, 3. The external preparation for skin according to claim 1, wherein the preparation is selected from dihydroxydimethoxybenzophenone-sulfonic acid and a salt thereof, 2,4-dihydroxybenzophenone and tetrahydroxybenzophenone. 4. 4. The external preparation for skin according to claim 1, wherein the external preparation for skin is an anti-aging cosmetic or a sunscreen cosmetic.