JP4798762B2 - Sunscreen cosmetics - Google Patents

Description

  The present invention relates to a sunscreen cosmetic. More specifically, the present invention relates to a sunscreen cosmetic containing an ultraviolet absorber made of a specific dibenzoylmethane derivative, wherein the light stability of the ultraviolet absorber is remarkably increased.

  The important ultraviolet absorption wavelength regions by sunscreen cosmetics are the UV-A region (320 to 400 nm) and the UV-B region (290 to 320 nm). UV rays in the UV-A region (320 to 400 nm) invade the skin black, but it is considered that sunburn occurs like the ultraviolet rays in the UV-B region (290 to 320 nm) and does not promote skin aging. It was. However, in recent years, ultraviolet rays in the UV-B region stay relatively on the surface of the skin, whereas ultraviolet rays in the UV-A region reach the deep part of the skin, and induce skin cancer as well as skin aging. It has been found to be the cause.

  Cosmetic UV absorbers that have been used to date are classified according to the structure: (1) benzoic acid derivatives, (2) cinnamic acid derivatives, (3) benzophenone derivatives, (4) dibenzoylmethane derivatives, (5) Salicylic acid derivatives and the like. In recent years, the ultraviolet absorbers (2) and (4) are frequently used.

  However, the ultraviolet absorbers listed above have their respective problems from a practical standpoint. For example, in the benzoic acid derivative of (1), for example, p-dimethylaminobenzoic acid-2-ethylhexyl is liquid and transparent, and has advantages that it is easy to handle, but there is a suspicion of safety including these derivatives. It has not been used in recent years. Further, the maximum absorption wavelength is in the vicinity of 290 nm, and the ultraviolet ray only in the UV-B region is absorbed.

  In the cinnamic acid derivative (2), there is p-methoxycinnamic acid-2-ethylhexyl ester as an ultraviolet absorber most frequently used in sun care cosmetics currently on the market. The maximum absorption wavelength is around 310 nm, and the absorption region does not reach the UV-A region. In addition, the color changes due to sunlight and there is a problem in the sustainability of the coloring property and the UV protection effect.

  In the benzophenone derivative of (3), for example, 2-hydroxy-4-methoxybenzophenone has absorption over the UV-A and UV-B regions and has relatively good solubility in a skin external preparation base, but has a maximum absorption wavelength. Slightly close to the UV-B region and the absorbance is not very large. In recent years, a basic skeleton structure (benzophenone) has been pointed out as an environmental hormone and its use has been avoided.

  Of the dibenzoylmethane derivatives of (4), 4-tert-butoxy-4-methoxydibenzoylmethane is often used as a skin external preparation. The maximum absorption is in the vicinity of 360 nm, the absorbance is large, and it is excellent as an ultraviolet absorber in the UV-A region.

In the salicylic acid derivative (5), octyl salicylate is used. It has a maximum absorption wavelength in the UV-B region, is oily, and is excellent in compatibility with paraffin oil or the like, but is not practically used because of its low absorbance.

  For this reason, 2-ethylhexyl p-methoxycinnamate (2) is used in the UV-B region, and 4-tert-butoxy-4-methoxydibenzoylmethane (4) is used in the UV-A region. Often done. Particularly in recent years, there has been an increasing demand for ultraviolet absorption in the UV-A region.

  However, as a problem of dibenzoylmethane derivatives such as 4-tert-butoxy-4-methoxydibenzoylmethane, which is well known as an ultraviolet absorber in the UV-A region, the light stability is poor. Deteriorates and a so-called ultraviolet absorber stamina down occurs. In addition, there is a problem that the compatibility with oils for cosmetics is poor and only a small amount can be mixed.

  In contrast, in order to improve the light stability of the dibenzoylmethane derivative, amino-substituted hydroxybenzophenone (Patent Document 1), alkyl β, β-diphenyl acrylate, or α-cyano-β, β-diphenyl acrylate Cosmetics containing (Patent Document 2) have been developed. However, the stability improvement is not always sufficient.

  On the other hand, external preparations for skin containing an alkylaryl 1,3-propanedione silicone derivative represented by the general formula (I) as an ultraviolet absorber are disclosed in Patent Document 3 and Patent Document 4.

JP 2003-192559 A Japanese Patent No. 2975682 JP-A-5-194543 JP 11-269050 A

  From the above viewpoint, the present inventors have conducted extensive research focusing on the problems of dibenzoylmethane derivatives that are UV-A ultraviolet absorbers. As a result, among dibenzoylmethane derivatives, 4- (1,1- When an alkylaryl 1,3-propanedione silicone derivative having a specific structure is blended with dimethylethyl) -4′-methoxydibenzoylmethane, the light stability of the ultraviolet absorber is surprisingly improved and the ultraviolet absorption effect is improved. The present inventors have found that stamina down can be suppressed and have completed the present invention.

  The object of the present invention is to significantly improve the light stability of sunscreen cosmetics containing dibenzoylmethane derivatives, which are highly used as UV absorbers in the UV-A region, and to suppress the stamina down of the UV absorption effect. In addition, an object of the present invention is to provide sunscreen cosmetics that are extremely excellent in UV-A absorption characteristics in the UV-A region.

That is, the present invention provides 4- (1,1-dimethylethyl) -4′-methoxydibenzoylmethane and an alkylaryl 1,3-propanedione silicone derivative comprising a compound represented by the following formula (III). The present invention provides a sunscreen makeup characterized by containing.
Formula (III)

  According to the present invention, in a sunscreen cosmetic compounded with a dibenzoylmethane derivative, its light stability is remarkably improved, the stamina down of the ultraviolet absorption effect is suppressed, and the ultraviolet absorption property in the UV-A region is extremely excellent. It is possible to provide sunscreen cosmetics.

  Hereinafter, the present invention will be described in detail.

“4- (1,1-Dimethylethyl) -4′-methoxydibenzoylmethane”
The dibenzoylmethane derivative used in the present invention is 4- (1,1-dimethylethyl) -4′-methoxydibenzoylmethane represented by the following formula. In the present invention, a commercially available product (Pulsol 1789: manufactured by DSM Nutritional Products) can be used.

"Alkylaryl 1,3-propanedione silicone derivative represented by general formula (I)"
The alkylaryl 1,3-propanedione silicone derivative of the general formula (I) is a known compound (see Japanese Patent No. 3229383).
Examples of R ¹ are hydroxyl group, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, t-butyl group, n-amyl group, isoamyl group, n-hexyl group, 2- Alkyl groups such as ethylbutyl group, n-octyl group, 2-ethylhexyl group, methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, s-butoxy group, t-butoxy group, n-amyloxy group And alkoxy groups such as isoamyloxy group, n-hexyloxy group, 2-ethylbutoxy group, n-pentyloxy group, n-octyloxy group and 2-ethylhexyloxy group.
R ² may be any alkyl group having 1 to 7 carbon atoms, but preferably has a secondary or tertiary carbon atom bonded to the carboxyl group. Particularly preferable examples of R ² include isopropyl group, tert-butyl group, ethylpropyl group, and ethylpentyl group.
R ³ may be any alkyl group having 2 to 10 carbon atoms. Examples of R ³ include —CH ₂ CH ₂ —, —CH ₂ CH ₂ CH ₂ —, —CH ₂ CH (CH ₃ ) CH. _{2 -, - CH (CH 3} ) CH 2 CH 2 -, - CH 2 CH 2 CH (CH 3) -, - CH 2 CH 2 CH 2 CH 2 -, - CH 2 CH 2 OCH 2 CH 2 -, hexylene , Cyclohexylene, decylene group, and the like, and an alkylene group having 2 to 4 carbon atoms is particularly preferable. Examples of R ⁴ include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a phenyl group and a trimethylsiloxy group. For this reason, it is preferable that the methyl group or a part thereof is a phenyl group or a trimethylsiloxy group.

M represents the number of substituents and is an integer of 0 to 3. n represents the number of repeating units of siloxane and is an integer of 0 to 3. p is 0 or 1.
R ⁴ may be the same or different, and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a phenyl group, and a trimethylsiloxy group. It is preferable that a part is a phenyl group or a trimethylsiloxy group.

又は、

第二段階
｛上記丸数字３の化合物｝＋｛分子内に一つのＳｉ−Ｈ基を含有する繰り返し単位数２〜５のシロキサン｝→ 一般式（ＩＩ） The alkyl-aryl 1,3-propanedione silicone derivatives used in the present invention include liquid or resinous solids at room temperature depending on the molecular weight, and any of them can be used as a UV-A absorber. The alkyl-aryl 1,3-propanedione silicone derivative of the present invention can be synthesized by the following two-stage reaction of the first stage Claisen condensation reaction and the second stage hydrosilylation reaction.
the first stage

Or

Second stage {Compound with the above circled number 3} + {siloxane having 1 to 5 repeating units containing one Si—H group in the molecule} → General formula (II)

In the above reaction formula, R ¹ , R ² , m, n, and p are defined by Chemical Formula ² , A is an alkyl group having 1 to 5 carbon atoms, and B is an alkenyl having 2 to 10 carbon atoms. Group or oxyalkenyl group. The first stage Claisen condensation reaction is described in R.C. Hauer et al., “Organic Reactions”, Vol. 8, p59, John Wiley and Sons Inc. , New York 1954, according to the present invention.

That is, a methyl alkyl ketone (circled number 1) or substituted acetophenone (circled number 5) and a fatty acid or substituted benzoic acid alkylphenyl (circled number 4) or a compound represented by the number 2 in the presence of a base such as an alkali alcoholate. In the presence of sodium hydride, hydroxide or amide compound, in a solvent such as toluene, isopropyl ether, tetrahydrofuran, 1,2-dimethoxyethane, dimethyl sulfoxide or dimethylformamide at room temperature to boiling point. An alkyl-aryl 1,3-propanedione derivative (circle numeral 3) can be obtained. The second stage reaction is a hydrosilylation reaction. It is known that this reaction is usually promoted by a platinum group metal, a platinum group metal compound, or a complex compound of the metal (Japanese Patent Laid-Open Nos. 60-108431, 60-210632, and 1-50711). Etc.)
Reaction of an alkylaryl 1,3-propanedione derivative (circled number 3) with a siloxane having 2 to 5 repeating units containing one SiH group is also possible using a conventional catalyst such as platinum supported on carbon or platinum chloride. The reaction is promoted with an acid, an acetylacetone platinum complex, a platinum complex with unsaturated compounds, an unsaturated siloxane platinum complex, a rhodium compound and a platinum compound complex.

The amount of 4- (1,1-dimethylethyl) -4′-methoxydibenzoylmethane is appropriately determined according to the target product, but is 0.5 to 5% by mass based on the total amount of the sunscreen cosmetic. Is preferable, and 1-3 mass% is further more preferable.
The amount of the alkylaryl 1,3-propanedione silicone derivative represented by the general formula (I) is appropriately determined according to the target product, but is 0.5 to 10 with respect to the total amount of the sunscreen cosmetic. % By mass is preferable, and 1 to 7% by mass is more preferable.

  In addition to the above essential components, the sunscreen cosmetics of the present invention are usually used in skin preparations such as cosmetics and pharmaceuticals, such as whitening agents, moisturizing agents, antioxidants, oily components, and other ultraviolet absorbers. , Surfactants, thickeners, alcohols, powder components, colorants, aqueous components, water, various skin nutrients and the like can be appropriately blended as necessary to produce them by conventional methods. For example, the following are mentioned as a compounding component.

Avocado oil, macadamia nut oil, corn oil, olive oil, rapeseed oil, evening primrose oil, castor oil, sunflower oil, teaseed oil, rice bran oil, jojoba oil, cacao butter, palm oil, squalene, beef tallow, owl, beeswax, candelilla wax Oils such as carnauba wax, whale wax, lanolin, liquid paraffin, polyoxyethylene (8 mol) oleyl alcohol ether, glyceryl monooleate, cyclomethicone, dimethylpolysiloxane, diphenylpolysiloxane.
Higher alcohols such as capryl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, cholesterol, phytosterol.
Higher fatty acids such as capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, lanolin fatty acid, linoleic acid, linolenic acid.
Moisturizers such as polyethylene glycol, glycerin, sorbitol, xylitol, maltitol, mucopolysaccharide, hyaluronic acid, chondroitin sulfate and chitosan.
Thickeners such as methylcellulose, ethylcellulose, gum arabic, and polyvinyl alcohol.
Organic solvents such as ethanol and 1,3-butylene glycol.
Antioxidants such as butylhydroxytoluene, tocopherol and phytic acid.
Antibacterial preservatives such as benzoic acid, salicylic acid, sorbic acid, paraoxybenzoic acid esters (such as ethylparaben and butylparaben), and hexachlorophene.
Amino acids and hydrochlorides such as glycine, alanine, valine, leucine, serine, threonine, phenylalanine, tyrosine, aspartic acid, asparagine, glutamine, taurine, arginine, histidine.
Organic acids such as acyl sarcosine acid (eg, lauroyl sarcosine sodium), glutathione, citric acid, malic acid, tartaric acid, lactic acid.
Vitamin A and its derivatives, vitamin B6 hydrochloride, vitamin B6 tripalmitate, vitamin B6 dioctanoate, vitamin B2 and its derivatives, vitamin B such as vitamin B12, vitamin B15 and its derivatives, ascorbic acid, ascorbic acid phosphate ( Salt), vitamin C such as ascorbic acid dipalmitate, α-tocopherol, β-tocopherol, γ-tocopherol, vitamin E acetate, vitamin E nicotinate and other vitamin E, vitamin D, vitamin H, pantothenic acid, pantethine, etc. Vitamins.
Nicotinamide, benzyl nicotinate, γ-oryzanol, allantoin, glycyrrhizic acid (salt), glycyrrhetinic acid and its derivatives, hinokitiol, mucidin, bisabolol, eucalyptol, thymol, inositol, saponins (psychosaponin, carrot saponin, loofah) Various drugs such as saponin, muclodisaponin, etc.), pantothenyl ethyl ether, ethinyl estradiol, tranexamic acid, cephalanthin, placenta extract.
Bark, Clara, Kouhone, Orange, Sage, Thyme, Yarrow, Zeni-oyster, Senkyu, Assembly, Spruce, Spruce, Birch, Sugina, Loofah, Maronie, Yukinoshita, Arnica, Lily, Mugwort, Peonies, Aloe, Gardenia, Sawara Natural extract extracted with solvent, alcohol, polyhydric alcohol, water, aqueous alcohol.
Cationic surfactants such as stearyltrimethylammonium chloride, benzalkonium chloride, and laurylamine oxide.
Metal sequestering agents such as disodium edetate, trisodium edetate, sodium citrate, sodium polyphosphate, sodium metaphosphate and gluconic acid.
Fragrance, scrub agent, purified water, etc.

  Particularly preferred bases for the sunscreen cosmetics of the present invention are decamethylcyclopentasiloxane, isononyl isononanoate, dimethylpolysiloxane, heptamethyloctyltrisiloxane, trimethylsiloxysilicic acid, liquid paraffin, squalane, cetyl isooctanoate, isooctanoic acid It is an oil component of triglyceride and di-2-ethylhexyl succinate. Especially this invention is preferably utilized for the sunscreen cosmetics which have decamethylcyclopentasiloxane as a main component base.

  The sunscreen cosmetics of the present invention may be in any product form, such as ointments, creams, emulsions, lotions, packs, and the like. The dosage form is not particularly limited.

  The present invention will be specifically described below with reference to examples. The present invention is not limited to these examples.

「化合物２」

「化合物３」

「化合物４」

「化合物５」

「化合物６」

「化合物７」

「化合物８」

「化合物９」

なお、前記化合物１〜９中、Ｓｉ₂、Ｓｉ₃、Ｓｉ₅はそれぞれ次の化学式で示される。
「Ｓｉ₂」

「Ｓｉ₃」

「Ｓｉ₅」

<Synthesis example of alkylaryl 1,3-propanedione silicone derivative represented by general formula (I)>
Preferred specific compounds include the following compounds 1 to 9, and of these, production examples of compound 1, compound 2, compound 5, compound 7, compound 8, and compound 9 are shown.
"Compound 1"

"Compound 2"

"Compound 3"

"Compound 4"

"Compound 5"

“Compound 6”

“Compound 7”

"Compound 8"

"Compound 9"

In the compounds 1 to 9, Si ₂ , Si ₃ and Si ₅ are represented by the following chemical formulas.
"Si ₂ "

"Si ₃ "

“Si ₅ ”

“Production Example of Compound 1”
1- (3-methoxy-4-allyloxyphenyl) -3-tert-butyl 1,3-propanedione 2.5 g, 1,1,1,3,3-pentamethyldisiloxane 1.7 g, toluene 20 ml To the mixed solution, 0.5 mg of hexachloroplatinic acid (IV) hexahydrate was added and reacted at 100 to 105 ° C. for 6 hours with stirring. After completion of the reaction, toluene was distilled off under reduced pressure, and the residue was separated and purified by silica gel column chromatography (eluted with a 2 v / v% ethyl acetate-hexane mixture) to obtain 2.6 g of a colorless oil. The yield was 68.4%. λ _max : 335 nm (ε = 24090), mass spectrum M ⁺ m / e 438

“Production Example of Compound 2”
13.0 g of 1- (3-methoxy-4-allyloxyphenyl) -3-tert-butyl 1,3-propanedione, 11.0 g of 1,1,1,3,5,5,5-heptamethyltrisiloxane Then, 0.03 g of a tetramethyldivinyldisiloxane platinum complex toluene solution (platinum content: 4 w / w%) was added to a solution of 30 ml of toluene, and the mixture was refluxed with stirring for 5 hours. After completion of the reaction, toluene was distilled off under reduced pressure and separated and purified by silica gel chromatography (eluted with a 2 v / v% ethyl acetate-hexane mixture) to obtain 10.2 g of the desired product. The yield was 47.1%. λ _max : 334 nm (ε = 23550), mass spectrum M ⁺ m / e 512

“Production Example of Compound 5”
1- (3-allyl-4,5-dimethoxyphenyl) -3- (1-ethylpentyl) -1,3-propanedione 3.4 g, 1,1,1,3,5,5,5-heptamethyl To a solution of 2.4 g of trisiloxane and 20 ml of toluene, 0.01 g of a tetramethylvinyldisiloxane platinum complex toluene solution (platinum content 4 w / w%) was added and reacted for 6 hours under reflux. After completion of the reaction, toluene was distilled off under reduced pressure, and the residue was applied to a silica gel column. Elution with a 1 v / v ethyl acetate-hexane mixture gave 4.1 g of the desired product. The yield was 73.2%.
Colorless oil λ _max : 334 nm (ε = 23500), mass spectrum M ⁺ m / e 568

“Production Example of Compound 7”
1- {3-methoxy-4- (2-methyl-2-propenoxy) phenyl} -3-tert-butyl-1,3-propanedione 25.1 g, 1,1,1,3,5,5,5 -0.05 g of the platinum catalyst described in Example 2 was added to a solution of 20.2 g of heptamethyltrisiloxane and 50 ml of toluene, and reacted at 100 ° C to 110 ° C for 18 hours. After completion of the reaction, toluene was distilled off, and the residue was distilled under reduced pressure to separate and purify the target product. Yield 28.8 g, pale yellow oil, boiling point bp 182-184 ° C./2 mmHg, λ _max : 334 nm (ε = 27350), mass spectrum M ⁺ m / e 526

“Production Example of Compound 8”
1- {3-methoxy-4- (4-pentenoxy) phenyl} -3-tert-butyl-1,3-propanedione 38.7 g, 1,1,1,3,5,5,5-heptamethyltri 29.7 g of siloxane and 0.02 g of the platinum catalyst described in Example 2 were dissolved in 70 ml of toluene, and reacted at 95 ° C. to 100 ° C. for 4 hours. After completion of the reaction, toluene was distilled off, and the residue was distilled under reduced pressure to obtain 39.7 g of the desired compound. Pale yellow oil, boiling point bp 215-225 ° C (bath temperature) / 2 mmHgλ _max : 334 nm (ε = 23220), mass spectrum M ⁺ m / e 540

“Production Example of Compound 9”
1- (3-methoxy-4-hydroxy-5-allylphenyl)-obtained by Claisen rearrangement reaction of 1- (3-methoxy-4-allyloxyphenyl) -3-tert-butyl-1,3-propanedione 18.4 g of 3-tert-butyl-1,3-propanedione (light yellow crystals, melting point 115-116 ° C.), 15.5 g of 1,1,1,3,5,5,5-heptamethyltrisiloxane 0.02 g of the platinum catalyst described in Example 2 was dissolved in 50 ml of toluene and reacted at 100 ° C. to 110 ° C. for 6 hours. After completion of the reaction, toluene was distilled off, and the residue was separated and purified by silica gel column chromatography (eluted with 7 v / v% ethyl acetate-hexane mixed solution) to obtain 21.7 g of the desired product. Pale yellow solid, mp 38-39 ° C. λ _max : 342 nm (ε = 24000), mass spectrum M ⁺ m / e 512

4- (1,1-dimethylethyl) -4′-methoxydibenzoylmethane in the blending amount shown in “Table 1” below is dissolved in glyceryl tri-2-ethylhexanoate as a cosmetic oil, and irradiated with light. The deterioration of ultraviolet absorption characteristics was investigated. The result is shown in FIG.
"Measurement method and conditions"
50 μL of the prepared sample was uniformly applied to a nylon membrane. After standing for 15 minutes, absorbance at 358 nm was measured with a spectrophotometer (initial value). After the measurement, 2h irradiation (3900 kJ / m ² ) was performed with SUNTEST XLS + (manufactured by Atlas), and the irradiated sample was again measured with a spectrophotometer (after the test). The test results were calculated according to the following formula.
Residual amount (%) = absorbance after test (358 nm) / absorbance before test (358 nm) × 100

Ａ：４−（１，１−ジメチルエチル）−４’−メトキシジベンゾイルメタン
Ｂ：ジエチルアミノヒドロキシベンゾイル安息香酸ヘキシル

（特許文献１記載のアミノ置換ヒドロキシベンゾフェノン誘導体）

Ｃ：式(ＩＩＩ）で表される化合物からなるアルキルアリール１，３−プロパンジオンシリコーン誘導体

Ｄ：トリ２−エチルヘキサン酸グリセリル

A: 4- (1,1-Dimethylethyl) -4′-methoxydibenzoylmethane B: Diethylaminohydroxybenzoyl hexyl benzoate

(Amino-substituted hydroxybenzophenone derivative described in Patent Document 1)

C: alkylaryl 1,3-propanedione silicone derivative comprising a compound represented by formula (III)

D: Glyceryl tri-2-ethylhexanoate

FIG. 1 is a graph in which the deterioration (stamina down) of ultraviolet absorption characteristics due to light irradiation is evaluated by the residual rate. As can be seen from this graph, 4- (1,1-dimethylethyl) -4′-methoxydibenzoylmethane is combined with an alkylaryl 1,3-propanedione silicone derivative comprising a compound represented by formula (III). It can be seen that the light stability is improved and the deterioration of the ultraviolet absorption effect can be remarkably suppressed.

The prescription example of the sunscreen cosmetics of this invention is given to the following.
"Example 4: Sunscreen cosmetic W / O emulsion"
mass%
1. Dimethylpolysiloxane 1
2. Decamethylcyclopentasiloxane 25
3. Trimethylsiloxysilicic acid 5
4). Polyoxyethylene methylpolysiloxane copolymer 1
5. Lauryl PEG-9 polydimethylsiloxyethyl dimethicone 1
6). Isononyl isononanoate 5
7). Dipropylene glycol 5
8). Dipotassium glycyrrhizinate 0.02
9. Glutathione 1
10. Thiotaurine 0.05
11. Clara extract 1
12 Paraben appropriate amount13. Phenoxyethanol appropriate amount14. 2-Ethylhexyl paramethoxycinnamate 7.5
15. Dimethyl distearyl ammonium hectorite 0.5
16. Spherical polyalkyl acrylate powder 5
17. Butylethylpropanediol 0.5
18. 4- (1,1-Dimethylethyl) -4′-methoxydibenzoylmethane 2
19. Alkyl-aryl 1,3-propanedione silicone derivatives of formula (II)
5
20. Hydrophobized zinc oxide or hydrophobically treated titanium oxide 15
21. Purified water Residual production method The aqueous phase was gradually added to the oil phase, and after completion of the addition, the emulsified particles were prepared to be uniform using a stirrer.

"Example 5: Sunscreen cosmetic O / W emulsion"
mass%
1. Polyoxyethylene hydrogenated castor oil 1
2. Dimethicone copolyol 0.5
3. Decamethylcyclopentasiloxane 15
4). Isostearic acid 0.5
5. Phenyltrimethicone 1
6). Hydrophobized titanium oxide 5
7. 4- (1,1-Dimethylethyl) -4′-methoxydibenzoylmethane 3
8). 2-methoxyhexyl paramethoxycinnamate 5
9. Alkyl-aryl 1,3-propanedione silicone derivatives of formula (III)
5
10. Silica 1
11. Citric acid 0.01
12 Sodium citrate 0.09
13. Paraben appropriate amount14. Phenoxyethanol appropriate amount15. Alcohol 5
16. Dynamite Glycerin 1
17. Succinoglucan 0.2
18. Cellulose gum 1
19. Ion-exchanged water Residual production method After preparing the aqueous phase of 9 to 18, it was gradually added to the oil phase of 1 to 8, and finally stirred using a homomixer.

"Example 6: Sunscreen cosmetic O / W / O emulsion"
mass%
1. Polyoxyethylene hydrogenated castor oil 0.5
2. Isostearic acid 0.2
3. 2-Ethylhexyl paramethoxycinnamate 7.5
4). Alkyl-aryl 1,3-propanedione silicone derivatives of formula (III)
2.0
5.4- (1,1-Dimethylethyl) -4′-methoxydibenzoylmethane 2.0
6). Decamethylcyclopentasiloxane 35
7). Polyoxybutylene polyoxypropylene glycol 2.0
8). Dimethyl distearyl ammonium hectorite 0.5
9. Hydrophobized titanium oxide 12.0
10. Citric acid 0.04
11. Sodium citrate 0.06
12 Dipropylene glycol 2.0
13. Methyl glucose 1.0
14 Dynamite Glycerin 1.0
15. Salt 0.1
16. Methyl paraben appropriate amount 17. Phenoxyethanol appropriate amount 18. Ion-exchanged water Residual production method The oil phase of 1 to 5 was gradually added to the water phase of 10 to 18 to obtain an O / W preparation. This formulation was gradually added to the oil phase of 6-9, and then stirred with a homomixer to obtain the desired sample.

  According to the present invention, in a sunscreen cosmetic compounded with 4- (1,1-dimethylethyl) -4′-methoxydibenzoylmethane, which is a dibenzoylmethane derivative, its light stability is remarkably improved and ultraviolet absorption is achieved. It is possible to provide a sunscreen cosmetic that suppresses the stamina of the effect and is extremely excellent in the UV-A absorption characteristics of the UV-A region.

It is a graph showing the photostability of 4- (1,1-dimethylethyl) -4'-methoxydibenzoylmethane dissolved in glyceryl tri-2-ethylhexanoate.

Claims (1)

It contains 4- (1,1-dimethylethyl) -4′-methoxydibenzoylmethane and an alkylaryl 1,3-propanedione silicone derivative composed of a compound represented by the following formula (III). To sunscreen cosmetics.
Formula (III)

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