JPH04134043A - New alpha-benzylidene ketone derivative, ultraviolet absorber and cosmetic containing said absorber - Google Patents

Abstract

NEW MATERIAL:alpha-Benzylidene derivative expressed by formula I [R is OH, alkoxy, alkenyloxy, aralkyloxy, carboxyl, alkoxycarbonyl or aminocarbonyl or two R form alpha-methylenedioxy; n is 1-3; x is 1-3C alkylene, carbonyl, O, S, 1-2C oxyalkylene or 1-2C thioalkylene). EXAMPLE:2-(4-Methoxybenzylidene)indane-1-one. USE:An ultraviolet absorber and cosmetic having sunburn preventing effect. The benzylidene derivative expressed by formula I has ultraviolet ray-absorbing action and has excellent light stability. PREPARATION:For example, a condensed-ring phenylketone expressed by formula II is condensed with a substituted benzaldehyde expressed by formula III in the presence of a base to provide the alpha-benzylidene ketone derivative expressed by formula I.

Description

Detailed Description of the Invention [Industrial Field of Application] The present invention provides a novel α-benzylidene ketone derivative that has an ultraviolet absorbing effect and excellent photostability, and a novel α-benzylidene ketone derivative containing the same, which is resistant to sunburn. This invention relates to ultraviolet absorbers and cosmetics with excellent UV protection effects.

[Conventional technology]

Ultraviolet rays are known to cause various changes in the skin. Dermatologically, the working wavelength is 400 to 320n.
Ultraviolet rays are divided into long-wavelength ultraviolet rays of m, medium-wavelength ultraviolet rays of 320 to 29 Or+m, and short-wavelength ultraviolet rays of 290 nm or less, and are called UV-8, UV-8, and LIV-C, respectively. The ultraviolet rays in sunlight are IIV-8 and IIV-8, and U
V-C is absorbed in the Saishin layer and hardly reaches the ground.

When UV-E is irradiated to the skin with a certain amount of light, it causes changes in the skin, such as the formation of erythema and chickenpox, as well as accelerated melanin formation and pigmentation.

On the other hand, UV-A causes a blackening effect on the skin (immediate blackening) immediately after irradiation, and as the energy reaches the dermis, it causes changes in blood vessel walls and elastic fibers in connective tissue. Such action of IIV-A accelerates skin aging and is thought to be a factor in the appearance of age spots, wrinkles, and freckles.

As the effects of ultraviolet rays on human skin have become clearer, compounds that absorb UV-A have been developed. It is said that it is desirable that such ultraviolet absorbers satisfy all of the following conditions.

■ Absorb IIV-A light as completely as possible.

■ Stable against light and heat.

■ No toxicity, irritation or other harmful effects on the skin.

■　Effects should last.

■ Excellent compatibility with cosmetic bases.

Conventionally, for example, dibenzoylmethane derivatives have been used as UV-A absorbers.

[Problem to be solved by the invention]

However, these conventional ultraviolet absorbers do not necessarily fully satisfy the above conditions, and in particular their stability against light is insufficient, and C1nt and JCosmetic 5ci, which are known to decompose or react with ultraviolet light,
ence, 10.53 (1988) E o Such decomposition of UV absorbers not only leads to a decrease in the duration of their effects, but also ignores the effects on the skin of the decomposed products themselves or the products generated by reactions with the formulations. I can't [Fragrance Journal, 84.34 (1987)].

Therefore, there has been a desire for an ultraviolet absorber that satisfies the above conditions, particularly an ultraviolet absorber that has excellent stability against light.

[Means to solve the problem]

In view of these circumstances, the present inventors have synthesized a number of α-benzylidene ketone derivatives and studied their properties, and found that a novel α-benzylidene ketone derivative represented by the general formula (1) below has excellent UV-resistance. The present invention was completed based on the discovery that it has an absorbing effect and is extremely stable against light, and that by blending it, a cosmetic with an excellent sunburn prevention effect can be obtained.

That is, the present invention relates to the following general formula M) (wherein, n R's may be the same or different, and each represents a hydroxyl group, an alkoxy group, an araloxy group, an aralkyloxy group, a carboxyl group, an alkoxycarbonyl group, or represents an aminocarbonyl group, or α-
A methylenedioxy group may also be formed. n represents an integer of 1 to 3; show)
The present invention provides an α-benzylidene ketone derivative represented by the following, and ultraviolet absorbers and cosmetics containing the α-benzylidene ketone derivative.

In the above general formula (1), specific examples of R include a hydroxyl group, a methoxy group, an ethoxy group, a propoxy group, an allyloxy group,
Examples include t-butoxy group, benzyloxy group, methylenedioxy group, carboxyl group, methoxycarbonyl group, ethoxycarbonyl group, dimethylaminocarbonyl group, diethylaminocarbonyl group, and the like. Specific examples of X include methylene group, ethylene group, propylene group, carbonyl group, oxygen atom, sulfur atom, oxymethylene group, oxyethylene group, thiomethylene group, thioethylene group, and the like.

The α-benzylidene ketone derivative (I) of the present invention can be produced, for example, according to the following formula.

(II) (I) [In the formula, R, n and α
- A benzylidene ketone derivative (I) is produced. The condensed phenyl ketone (n) used in this reaction is 1
-indanone, 1,3-indanedione, dihydrobenzofuran-3-one, dihydrobenzothiophen-3-one, tetralone, dihydrochromone, dihydrothyran-4-one, penzosuberone and the like.

On the other hand, as the substituted benzaldehyde (I [I), 0-methoxybenzaldehyde, m-methoxybenzaldehyde, p-methoxybenzaldehyde, 2,3-dimethoxybenzaldehyde, 2.4-dimethoxybenzaldehyde, 3,4-dimethoxybenzaldehyde, 3,4 .5
-) Dimethoxybenzaldehyde, 3,4-methylenedioxybenzaldehyde, 0-hydroxybenzaldehyde, m-hydroxybenzaldehyde, p-hydroxybenzaldehyde, 0-formylbenzoic acid and its esters and its amides, m-formylbenzoic acid and its esters and amides thereof, p-formylbenzoic acid and esters thereof, and amides thereof.

This reaction is carried out in a protic solvent such as methanol, ethanol, isopropanol, or an aprotic solvent such as benzene, toluene, xylene, or tetrahydrofuran, using a base as a catalyst at 20 to 150°C for several tens of tens of minutes. It is preferable to do it for an hour. Examples of the base used here include metal alkoxide compounds such as sodium methoxide, sodium ethoxide, and potassium t-butoxide; metal hydroxides such as sodium hydroxide and potassium hydroxide.

α-Benzylidene ketone derivative (1) thus obtained
In the ultraviolet absorber of the present invention containing α-benzylidene ketone derivatives (1), one or more of these α-benzylidene ketone derivatives (1) may be used as they are, but it is preferable that they be mixed in addition to a carrier.

The carrier may be any carrier as long as it is inert to the α-benzylidene ketone derivative (1), and may be solid, liquid, emulsion, foam, gel, or the like.

Typical examples include water, alcohol, fats and oils (e.g. hydrocarbon oil, fatty acid ester, long chain alcohol, silicone oil), fine powder of starch or talc, etc.
Examples include low-boiling hydrocarbons or halogenated hydrocarbons used as aerosol propellants. The ultraviolet absorber of the present invention further includes the α-benzylidene ketone derivative of the present invention (
Other ingredients such as preservatives, fragrances, colorants, surfactants, etc. may be added as long as they do not impair the ultraviolet absorbing effect of I).

The cosmetic containing the α-benzylidene ketone derivative (I) (hereinafter referred to as the "cosmetic of the present invention") is one type of α-benzylidene ketone derivative (1) that has an affinity for the cosmetic base. Or, it can be prepared by selecting two or more of them as appropriate and blending them into a known cosmetic base by a conventional method to form a dosage form such as a cream, solution, oil, spray stick, milky lotion, foundation, or ointment.

That is, by selectively using the α-benzylidene ketone derivative (1) in accordance with the cosmetic base, oil-based cosmetic oils, oil-based creams and emulsions that contain a large amount of oil, and weak oil-based cosmetics that contain a large amount of water can be used. Manufacture all types of cosmetics that have UV absorption properties, from basic cosmetics such as oil-based creams, weak oil-based emulsions, and water-based lotions to makeup cosmetics such as oil-based foundations and lipsticks. I can do it. Suitable bases and solvents for this include hydrocarbons, such as solid or liquid paraffin, crystal oil, ceresin, osichelite or montan wax; vegetable or animal fats, such as olive, earth wax, carnauba wax, lanolin or spermaceti. Furthermore, fatty acids and their esters such as stearic acid, palmitic acid, oleic acid, glycerin monostearate, glycerin distearate, glycerin monooleate, isopropyl myristate, isopropyl stearate or butyl stearate; Examples include alcohols such as ethyl alcohol, isopropyl alcohol, heptyl alcohol, stearyl alcohol, palmityl alcohol, and hexyldodecyl alcohol.

Further, polyhydric alcohols having a moisturizing effect such as glycol, glycerin or sorbitol can also be used.

The amount of the α-benzylidene ketone derivative in the ultraviolet absorber and cosmetics of the present invention is not particularly limited as it may vary depending on the form of use, and it is sufficient that it is present in an effective amount, but generally 0.1% in the crude product. ~20% by weight, preferably 0.5-1
It is preferable to mix it so that it is 0% by weight.

The UV absorbers and cosmetics of the present invention may contain only α-benzylidene ketone derivatives, but may also contain other UV-8
It is more preferable to use it as an ordinary sunscreen cosmetic in combination with an absorbent or UV absorber. Examples of such UV-e absorbers include p-methylbenzylidene-D, L-camphor or its sulfonic acid sodium salt; 2-phenylbenzimidazole-5-sulfonic acid sodium salt, 3.4-dimethylphenylglyoxylic acid. Sodium salt, 4-phenylbenzophenone, 4-phenylbenzophenone-2'-carboxylic acid isooctyl ester, p-methoxycinnamic acid ester, 2-
Examples include phenyl-5-methylbenzoxazole and p-dimethylaminobenzoic acid esters. II
As a VA absorbent, 4-methoxy-2'-carboxydibenzoylmethane, 4-methoxy-4'-t-butyldibenzoylmethane, 4isopropyldibenzoylmethane, 2-hydroxy-4-methoxybenzophenone or dibenzylidene is used. Examples include camphor.

In addition to the above-mentioned components, various additives can be added to the cosmetic composition of the present invention. Suitable additives include, for example,
Emulsifiers of the 110 and O/1'1 types may be mentioned.

As the emulsifier, commercially available emulsifiers can be used. Thickeners such as methylcellulose, ethylcellulose or carboxymethylcellulose, polyacrylic acid, tragacanth, agar or gelatin can also be added as additives. Furthermore, fragrances, preservatives, humectants, emulsion stabilizers, medicinal ingredients, and/or physiologically acceptable colorants may be added as necessary.

[Example] The present invention will be described in more detail by giving test examples and examples.

2 Example 1 Synthesis of 2-(4-methoxybenzylidene)indan-1-one compound (Ia) represented by R=-OCR, n=IX=-CL- in the general formula (1): Stirring device , 100 mj with reflux condenser and nitrogen inlet tube! In the Mitsuro flask, 1-indanone 2.0g (15.1mm01),
p-Methoxyhensteltecht 2J g (16,9m
moA) was dissolved in 50 ml of ethanol, 0.3 g (4.54 mmol) of potassium hydroxide was added thereto, and the mixture was stirred and reacted at room temperature under a nitrogen stream for 2 hours. The precipitated crystals were collected by filtration, and the pale yellow crystals obtained by washing with methanol were recrystallized from ethanol to obtain 3.5 g of the desired product in the form of pale yellow needle crystals. Yield 92.6%.

mp, 139-140℃ IR Niji Mmr1696.162B, 1604.15
18.1260°1186 cm-''H-NMR: δ (CDCj! 3) 3
．． 87 (311, s), 4.0N2H, s).

6.98 (2H, d, 8.8Hz), 7.42 (l
tl, t, 7.5Hz).

7.5-7.7 (3H, m), 7.65 (2H, d,
8.8Hz)7,90 (LH,d, 7.6Hz
) Example 2 2-(4-carboxybenzylidene)indan-1-one [-R in Funato (I)--CO2fl, n=IX--
C) Synthesis of compound (Ib) represented by 12-: 1 equipped with a stirring device, a dropping funnel, a reflux condenser and a nitrogen inlet tube
00mj! In a Mitsuro flask, 2.27 g of 4-carboxybenzaldehyde (KO of 15.1 mm) I
1.1 g (16.7 mmoj ethanol 10
mj! and water 5 mj! Dissolve in a mixed solvent with and stir at room temperature.

Here is 2.0g of 1-indanone (15.1mmoj?
) of ethanol 20m j! After the solution was added dropwise over 1 hour, stirring was continued for another 1 hour, and the precipitated crystals were collected by filtration. The obtained crystals were immersed in 20mj of chloroform! Suspended in 2NH
After neutralization with C1, the crystals were collected by filtration and recrystallized from ethanol to obtain 1.5 g of the desired product as a pale yellow powder. Yield 37.6%
.

IR Niji, 3000~2500br, 169
9.1676, 162g.

1325, 1299.766, 728 am')l-
NMR: δ(CDCJ!-+DMSO-d,)
4. lN2H,s).

7.4-7.8 (4H, m), 7.74 (2H, d
, 8.4Hz) 7.90 (LH, d, ?, 5t
lz), 8.13 (2H, d, 8.3flz)
Example 3 2-(2-hydroxybenzylidene)indan-1-
On [-Sailor (I) with R-1 leaf, n=1゜X=-CH2
- Synthesis of compound I (Ic) = 1-indanone 1.0 g (7,57 mmoA), salicylaldehyde 1.0 g (8,19 mmoffl), potassium hydroxide 0.9 g (13,6 mmoj!), x
Tanol 30mj? 2 in the same manner as in Example 1 using
The reaction was carried out for 0 hours, and 0.85 g of the target product in the form of yellow granular crystals was obtained.

Yield 47.5%.

Melting point 168℃ (decomposition) IR NijillBr 3220.166B, 1599
．． 1455.1359゜1332, 1305.1257
．． 1236.1125°747,732'H-NMR: δ (CDoOD+DMSO-d,
) 4.04 (2H, s).

6.8-8.2 (9H, m) Example 4 2-(4-methoxybenzylidene) -1,2,3,4
Synthesis of -tetrahydronaphthalen-1-one [-Shipin% formula% compound] (Id) 1-tetralone 2.0g (13,7mmoJ2)
, p-methoxybenzaldehyde2. Og (14,7
mmoJ>, potassium hydroxide 28 mg (0,42 mm
oj! ) and ethanol 2Q+r+1 in the same manner as in Example 1 for 3 hours to obtain the desired product 1 as pale yellow crystals.
．． 5g was obtained. Yield 41.4%.

'H-NMR: δ(C[lC(l a)
2.94 <2tl, t, 5.81(z)
.

3.15 (2H, t, 5.8Hz), 3.85 (3
ft, s).

6.9-8.2 (9fl, m) Example 5 2-(4-carboxybenzylidene) -1,2,3゜4-tetrahydronaphthalen-1-one [-Shipin% formula% compound represented by] ( Synthesis of Ie): 1-tetralone 2.0 g (13,7 mmoA), 4
-Carboxybenzaldehyde (13.3 mmol)
, potassium hydroxide 1.1g (16.7mm),
8 in the same manner as in Example 2 using a mixed solvent of 10 mβ of methanol and 5 ml of water and 20 mA of methanol.
The reaction was allowed to proceed for a period of time to obtain 1.0 g of the desired product as a pale yellow powder.

Yield: 26.2%.

Melting point 220~223℃ ■R; Sea 5r 3070~2550br, 1689.
160g, 1426°1296, 1250cm
-''H-NMR: δ(CDCj!,) 2.98(2H
, t), 3.14 (2H, t).

7, 2-8.2 (9)1. m) Example 6 6-(4-Methoxybenzylidene)benzocyclohebut-5-one [-R=-OCIl in Shipin (I).

n=1. Compound represented by X --CLCLCL-]
Synthesis of (If): 1-penzosuberone 1.0 g (6,24 mmotl)
, TI) methoxybenzaldehyde (], 9g (
6,61 mmoj! ), potassium hydroxide 0.2g (
3,03 mmo, &) and ethanol 15+nj! The mixture was reacted for 2 hours in the same manner as in Example 1 to obtain 1.1 g of the desired product as pale yellow crystals.

Yield: 64.3%.

'H-NMR: δ(CDCj!3) 2.08(2
H, Quint, 6.8Hz) 2.63(2H,t,
6.8Hz), 2.89(2fl, t,
6.811z) 3.85 (3H, s), 6.95
(2H, 8B, 8.8) 1z) 7.50 (2tl
AB, 8.8tlz), 7.1~7.9(
5N, m) Example 7 2-(4-methoxybenzylidene) indane 1,3-dione [-Funenin (I), R=-OCH3, nl, X--C
Compound represented by o-: Synthesis of l (Ig): 2.0 g of 1,3-indanedione (13,7 mmoβ
), 4-methoxybenzaldehyde 2.05g (15
, 1mmop), potassium hydroxide 0.3g (4,54
A reaction was carried out for 200 hours in the same manner as in Example 1 using mmoj and 50 ml of ethanol to obtain the target product 1 as yellow crystals.
．． 3g was obtained.

Yield: 35.9%.

') I-NMR: δ(CD[:A,) 3°92
(3)1. s), 7.02 (2H.

AB, 9.0Hz), 7.7~B, H2N, m)
, 8.56 (2H.

AB, 9.0Hz) Example 8 2-(4-carpoxybenzylene)indan 1.3
-Zion [-Seaman (I) and R--CO2H, nl, X-
Synthesis of compound represented by -Co- (Ih); 2.0 g (13,7 mmon) of 1,3-indanedione
>, 4-carboxybenzaldehyde 2.0g (1
3.3 mmoj2), potassium hydroxide 1.2 g (18
, 2mmoA), methanol 20m i! and water 20m
j! Mixed solvent with and further methanol 20m j! The mixture was reacted for 8 hours in the same manner as in Example 2 to obtain 1.2 g of the desired product in the form of pale yellow crystals.

Yield: 32.4%.

') I-NMR: δ (CD, OD+MSO-d
6) 7.9~B, H5fl, m).

8.07 (2L AB, 8.3Hz), 8.53 (
2H,AB, 8.4Hz) Example 9 3-(4-methoxybenzylidene)chroman-4-one [
-Sailor (I) R-QC)13. n=1.

X = -0CI1. - Compound] (Ii)
Synthesis: 100+nj! equipped with a stirrer, reflux condenser, Dean-Stark dehydrator and nitrogen inlet tube! 4-chromanone 1.0g (6.64m
moA), p-methoxybenzaldehyde 1.0g (
7.3 phase moj? ), sodium methylate 0.4g
(7,40mmoA) and dry benzene 50o+
j! The mixture was mixed and refluxed for 2 hours under a nitrogen stream to remove the water produced. After cooling, neutralize with 2N hydrochloric acid and extract with chloroform. After drying the solution over magnesium sulfate, the solvent was distilled off, and the resulting crude product was recrystallized from methanol to obtain 0.24 g of the desired product in the form of pale yellow needles. Yield 13.6
%.

Melting point 132-133℃ IR; ShiMBr166B, 1610.1514.14
80.1468°132B, 1312.1254.1
212.1030°1016,754 cm''11-NMR: δ(CDCβ3)3.87 (3H,
s), 5.38 (2H, d.

1.8Hz), 6.97 (2B, 8B, 8
．． 8Hz), 7.29 (2H.

AB, 8.8Hz), 7.84(Ift, br
s), 7.0 to 8.1 (4fl, m) Example 10 3-(4-methoxybenzylidene)-1,2,3,4tetrahydro-1-thianaphthalen-4-one [-Funenin (
I) with R--OCH=, n=1. X5C) Compound represented by I2-: Synthesis of (Ij): 1-thiochroman-4-one 1.0 g (6,09 mmo fl
), p-methoxybenzaldehyde 0.9 g (6
, 61 mmof fl ), potassium hydroxide 0.2 g (
Using 3,03 mmoj2 ) and 50 ml of ethanol, the reaction was carried out in the same manner as in Example 1 for 5 hours to obtain 0.74 g of the desired product as a pale yellow powder.

Yield: 43.0%.

Melting point 114-116℃ IR Niji K11r1677, 1653.1596.15
09.1443°1302, 1260.1212.11
79 c+n-''H-NMR: δ(CDCj! 3
) 3.85 (3H, s), 4.15 (2H, d.

1.011z), 6.96 (2H, AB, 8.8H
z), 7.38 (2H.

8B, 8.8flz), 7.75(IH, br
s), 7.2 to 7.5 (411, m) Test Example 1 Ultraviolet absorption effect of the α-benzylidene ketone derivative (I) of the present invention: As the α-benzylidene ketone derivative of the present invention (I Using the compounds of a) to (Ij) and 2-hydroxy-4-methoxybenzophenone, which is an IIV-A absorber, as a comparative compound, the ultraviolet absorption effect (absorbance) was measured by the method described below. The results are shown in Table 1.

(Measurement method) 2.5X 10-5 mo of the present invention compound and comparative compound
After preparing a 21 fl degree ethanol (99.5% reagent special grade) solution and placing it in a quartz cell (1 cm x 1 cm),
Measurement was performed using a U=3410 type self-recording spectrophotometer manufactured by Hitachi.

Below margin Ia: 2-(4-methoxybenzylidene)indan-1
-one Ib: 2-(4-carboxybenzylidene)indan-
1-one Ic: 2-(2-hydroxybenzylidene)indan-
1-one Id: 2-(4-methoxybenzylidene)-1,2゜3
4-tetrahydronaphthalen-1-one Ie:2-(4
-carboxybenzylidene)-1,2゜3.4-tetrahydronaphthalen-1-one If: 6-(4-methoxybenzylidene)benzocyclohebut-5-one Ig: 2-(4-methoxybenzylidene) indan-1
,3-dione Ih:2-(4-carboxybenzylidene)indan-
1,3-dione Ii: 3-(4-methoxybenzylidene)chroman-4
-one Ij: 3-(4-methoxybenzylidene)-1,2゜3
．． 4-tetrahydro-1-thianaphthalene 4-one Comparative compound 1: 2-hydroxy-4-methoxybenzophenone - Stronger absorption effect than methoxybenzophenone,
It has been shown to have a high sun protection effect.

Test Example 2 Stability of the α-benzylidene ketone derivative of the present invention against ultraviolet light: Using the compounds (I a) to (I j) obtained in the above examples, 4-methoxy-4't-butyldibenzoyl was used as a comparative compound. Using methane, stability against ultraviolet light was tested by the following experimental method. The results are shown in Table 2.

(Experimental method) The compound of the present invention and the comparative compound were dissolved in a solvent of 99.5% ethanol/distilled water (3/2) to a concentration of 2 mmoj2/β, which had a wavelength and intensity very close to sunlight. Ultraviolet rays were irradiated for 14 hours using a xenon needle tester. After distilling off the solvent, quantitative analysis was performed and stability was evaluated from the residual rate. The results are shown in Table 2.

Table 2 Photostability evaluation of dibenzoylmethane From the results in Table 2, compared to 4-methoxy-4'-t-butyldibenzoylmethane, which is commonly used as a UV-A absorber, the compounds of the present invention are more resistant to ultraviolet rays. It is clear that the stability is excellent.

Example 11 O/W type cream The following composition was blended according to a conventional method to prepare an O/W type cream.

〔composition〕

*4 methoxy 4′ -t-butyl Compound of the present invention (Ia) stearic acid Lipophilic monostearic acid glyceride polyoxyethylene sorbitan mono stearate Heptyl alcohol stearyl alcohol Squalane liquid paraffin 1.0 1.0 20.0 Vaseline butyl paraben Methylparaben triethanolamine glycerin Incense fee water Example 12 W10 type cream: Mix the following composition according to the usual method, - A sample was prepared.

〔composition〕

Compound of the present invention (Ib) Sorbitan sesquioleate Aluminum stearate Cetyl alcohol Liquid paraffin Squalane 5.0 0.1 0.1 1.0 10.0 Appropriate amount Balance 100, 0 W10 type chestnut (wt%) 2.0 4.0 0.5 4.0 16.0 10.0 Sodium myristate isopropyl benzoate Glycerin flavored water 0.3 10.0 Appropriate amount balance 100,0 Example 13 0/W type emulsion: The following composition was A ○/W type emulsion was prepared by blending according to the method.

〔composition〕

Compound of the present invention (Ic) stearic acid Sorbitan monostearate Polyoxy monostearate ethylene sorbitan cetyl alcohol stearyl alcohol Isopropyl myristate 0.4 7.0 Squalane liquid paraffin solid paraffin ethylparaben Methylparaben carbo balls caustic potash Incense water 5.0 5.0 2.0 0.1 0.1 0.2 0.4 Appropriate amount balance ioo,.

Example 14 Lotion: A lotion was prepared by blending the following composition according to a conventional method.

〔composition〕

Compound of the present invention (I d) Polyoxyethylene (23) lauryl ether ethanol (wt%) 2.0 4.0 10,0 Glycerin 3.0 Dipropylene glycol 7.0 Lactic acid
005 Sodium lactate 0.12 Methylparaben 0.1 Fragrance
suitable scenery
elementary minute
Quantity water rose ″1
00,0 [Effect of the invention] Since the α-benzylidene ketone derivative (I) of the present invention has excellent ultraviolet absorbing action and excellent stability, ultraviolet absorbers or cosmetics containing it have a sunburn prevention effect. It is excellent.

that's all

Claims (1)

[Claims] 1. The following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, n R's may be the same or different, and each represents a hydroxyl group or an alkoxy group. , an alkenyloxy group, an aralkyloxy group, a carboxyl group, an alkoxycarbonyl group or an aminocarbonyl group, or two R's may form an α-methylene-dioxy group. n is an integer of 1 to 3. X is an alkylene group having 1 to 3 carbon atoms, a carbonyl group, an oxygen atom, a sulfur atom, or an alkylene group having 1 to 3 carbon atoms.
2 oxyalkylene group or thioalkylene group having 1 to 2 carbon atoms). 2. An ultraviolet absorber containing the α-benzylidene ketone derivative according to claim 1. 3. A cosmetic containing the α-benzylidene ketone derivative according to claim 1.