KR900002058B1 - Bernzylidene compounds cosmetic compositions containing the same and ultraviolet absorber comprising the same - Google Patents

Abstract

Benzylidene cpds. of formula (I), cosmetic compsns. and UV absorbers contg. (I) are prepared. In (I), A is a gp. of (a) or (b); B is H or acetyl; W is H or -CH2-CH2-CO-O-R; Y is O or -NH-; Z is methyl or phenyl; R is C1-18 straightchain alkyl or C3-18 branched or cyclic alkyl; X1, X2 and X3 are each H, OH or methoxyl. (I) can be used in synthetic resins to prevent breakdown by UV radiation.

Description

Benzylidene Compound, Cosmetic Composition Containing It And Ultraviolet Absorber Including It

1 to 19 show infrared absorption spectra of compounds Nos. 1 to 19 according to the present invention, respectively.

The present invention relates to novel benzylidene compounds, ultraviolet absorbent cosmetic compositions and ultraviolet absorbents. In particular, the present invention provides an ultraviolet absorbent cosmetic composition containing at least one benzylidene compound represented by the following general formula (I), a benzylidene compound represented by the general formula (I), and benzylidene represented by the general formula (I). A ultraviolet absorbent comprising at least one compound.

Wherein A is a group represented by the following general formula (II) or (III);

In the above, B represents a hydrogen atom or an acetyl group; W represents a hydrogen atom or -CH ₂ -CH ₂ -CO-OR; Y represents an oxygen atom or an imino group (-NH-); Z represents a methyl group or a phenyl group; And R represents a straight chain alkyl group having 1 to 18 carbon atoms, or a branched or cyclic alkyl group having 3 to 18 carbon atoms; X ¹ and X ² and X ³ independently represent a hydrogen atom, a hydroxyl group or a methoxyl group (two or three of X ¹ , X ² and X ³ may be the same or all may be different); Provided that when A is a group represented by formula (II), R is not an alkyl group having from 1 to 2 carbon atoms, A is a group represented by formula (III) and X ¹ , X ² and X ³ are hydrogen R is not an alkyl group having from 1 to 2 carbon atoms.

In the field of cosmetics, the use of ultraviolet absorbers for preventing adverse effects of ultraviolet rays on the skin has long been noted, and numerous ultraviolet absorbers have been developed for use in cosmetics.

When the skin is exposed to ultraviolet light, ultraviolet light causes various changes in skin tissue. In dermatology, ultraviolet rays are classified into long wavelength ultraviolet rays (400-320 nm), medium wavelength ultraviolet rays (320-290 nm) and short wavelength ultraviolet rays (290-100 nm), which are UV-A, UV-B and UV-C, respectively. do.

Among them, UV-C is absorbed by the ozone layer and hardly reaches the earth's surface. With UV-B it is known that when the skin is exposed to a certain level of UV-B, UV-B causes erythema or blisters on the skin or causes pigmentation on the skin. UV-A, meanwhile, has been said to have little effect on the skin. However, as a result of electron microscopy and histological studies, it has recently been discovered that UV-A causes changes in the elastic fibers of blood vessel walls or connective tissue. UV-A also hurts sensitive skin or skin that has been exposed to sunlight for a long time. UV-A also enhances the action of UV-B (J. Willis, A. Kligman and J. Epstein: "Photo-enhancement", The Journal of Investigative Dermatology, Vol. 59, No. 6, P. 416, 1973) has been reported. Therefore, screening the skin from UV-A is as important as screening from UV-B.

As the UV-B absorbent, a benzophenone absorbent, a salicylic acid absorbent, a cinnamic acid absorbent, a paraaminobenzoic acid absorbent and the like are used. However, none of these known ultraviolet absorbents are satisfactory in terms of effects, safety, solubility, stability and other properties.

The history of research on UV-A is not long, and few substances are known to effectively absorb UV-A when applied to the skin. Known as such substances are dibenzoylmethane derivatives, cinnamic acid derivatives and calcon derivatives [West German Patent Application Nos. 2,728,241 and 2,728,243 and Japanese Patent Laid-Open Nos. 51-61641 ('76) and 52-46056 ( '77, 57-59840 ('82), 57-19720 ('82) and 60-109544 ('85).

(여기서, R은 1 내지 3개 탄소원자를 갖는 알킬기임) 화합물을 함유하는 광발연제를 기재하고 있고, 또 일본국 특개소 제52-46056호('77)는For example, Japanese Patent Laid-Open No. 51-61641 ('76) is a general formula with a blendable cosmetic developer

(Wherein R is an alkyl group having from 1 to 3 carbon atoms) A photofoaming agent containing a compound is disclosed, and Japanese Patent Laid-Open No. 52-46056 ('77)

Containing at least one compound represented by (wherein R and R ¹ are linear or branched alkyl groups having 1 to 8 carbon atoms, n is an integer of 0 to 3 and n 'is an integer of 1 to 3) It describes a UV absorber. Japanese Patent Application Laid-Open No. 57-59840 (782) describes a composition having the property of protecting the skin from ultraviolet rays, including at least one dibenzoylmethane derivative represented by the following general formula and a carrier acceptable for cosmetics.

는 무기산 또는 유기산으로부터 유도된 음이온을 나타냄. 일본국 특개소 제57-197209호('82)는 광발연재로 하기 일반식의 디벤조일메탄의 히드록실 유도체 1개 이상 및 화장품용으로 수용가능한 담채를 포함하는 조성물을 기술하고 있다.Wherein R ¹ and R ² represent a lower alkyl group or a hydroxyalkyl group; R ³ represents a lower alkoxy group or an alkoxy group; n is an integer from 0 to 3; In addition

Represents an anion derived from an inorganic or organic acid. Japanese Patent Application Laid-Open No. 57-197209 ('82) discloses a composition comprising at least one hydroxyl derivative of dibenzoylmethane of the following general formula as a light-emitting material and an acceptable color for cosmetics.

Wherein R ¹ , R ² , R ³ and R ⁴ represent a hydrogen atom, a halogen atom, a straight or branched alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms; And R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. In addition, Japanese Patent Application Laid-Open No. 60-109544 ('85) discloses an ultraviolet absorber containing a calcon derivative represented by the following general formula as an active ingredient.

Wherein R ¹ represents a hydrogen atom or a methyl group; And R ² represents a straight or branched aliphatic hydrocarbon group having 2 to 24 carbon atoms.

In addition to the above-described ultraviolet absorbents, inorganic powders having the action of physically reflecting or scattering ultraviolet rays such as titanium dioxide, zinc oxide, iron oxide and the like are also used.

The benzophenone ultraviolet absorber has an activity of absorbing long wavelength ultraviolet rays (320-400 nm), but is low in absorption of medium wavelength ultraviolet rays (290-320 nm) which causes skin blisters and the like.

Paraaminobenzoic acid and cinnamic acid ultraviolet absorbers have a high UV absorption effect, but have problems in stability. Since the salicylic acid UV absorber has a low UV absorption effect, a satisfactory effect cannot be expected unless a large amount of these are combined.

Inorganic powders are limited in use to certain cosmetic forms with which they can be mixed, and they also have the problem that they can be colored when mixed in large quantities.

UV absorbers are also used as additives to prevent the degradation of the resin. As an additive, a salicylic acid UV absorber, a benzophenone UV absorber, a triazole UV absorber, and a cyanoacrylate UV absorber are mentioned. However, while triazole UV absorbers have problems in terms of stability and hygiene, salicylic acid and benzophenone UV absorbers have an absorbance of ultraviolet radiation in the vicinity of 300-320 nm which affects resins such as polyethylene, polypropylene and polyvinyl chloride. low.

As described above, numerous ultraviolet absorbers have been developed, but no ultraviolet absorber that satisfies all requirements for UV absorbency, safety, solvent and solubility and stability in resins could not be obtained. Therefore, there has been a need for the realization of ultraviolet absorbers having excellent UV absorbency, safety and stability, and cosmetic compositions containing such UV absorbers.

In view of the above, according to the results of a wider study, the benzylidene compound represented by the following general formula (I) has a high ultraviolet absorption of medium wavelength (240-400 nm) and various kinds of animal oil, vegetable oil, fat and oils and fats. And a cosmetic composition easily soluble in an organic solvent and containing one or more of these compounds, having good UV absorption, preventing skin erythema, and light and heat stability, and also having skin, lips, hair, nails, and the like. It was found to be neither irritating nor damaging. The present invention has been completed based on this finding.

A first object of the present invention is to provide a benzylidene compound represented by the following general formula (I).

Wherein A is a group represented by the following formula;

인 경우, R은 1 내지 2개 탄소원자를 갖는 알킬기가 아니며, 또 A가

이고 또 X¹, X²및 X³이 수소인 경우 R은 1 내지 2개 탄소원자를 갖는 알킬기가 아님.Wherein B represents a hydrogen atom or an acetyl group; W represents a hydrogen atom or -CH ₂ -CH ₂ -CO-OR; Y represents an oxygen atom or an imino group (-NH-); Z represents a methyl group or a phenyl group; And R is a linear alkyl group having 1 to 18 carbon atoms, or a branched or cyclic alkyl group having 3 to 18 carbon atoms; X ¹ , X ² and X ³ are independently a hydrogen atom, a hydroxyl group or a methoxyl group (Two or three of which may be the same or both may be different);

R is not an alkyl group having 1 to 2 carbon atoms, and A is

And when X ¹ , X ² and X ³ are hydrogen, R is not an alkyl group having from 1 to 2 carbon atoms.

A second object of the present invention is to provide a cosmetic composition containing at least one compound of the following general formula (I).

Wherein A is a group represented by the following formula;

인 경우, R은 1 내지 2개 탄소원자를 갖는 알킬기가 아니며, 또 A가

이고 또 X¹, X²및 X³이 수소원자인 경우, R은 1 내지 2개 탄소원자를 갖는 알킬기가 아님.Wherein B represents a hydrogen atom or an acetyl group; W represents a hydrogen atom or -CH ₂ -CH ₂ -CO-OR; Y represents an oxygen atom or an imino group (-NH-); Z represents a methyl group or a phenyl group; And R represents a straight chain alkyl group having 1 to 18 carbon atoms, or a branched or cyclic alkyl group having 3 to 18 carbon atoms; X ¹ , X ² and X ³ independently represent a hydrogen atom, a hydroxyl group or a methoxyl group (two or three of which may be the same or both may be different); With A

R is not an alkyl group having 1 to 2 carbon atoms, and A is

And when X ¹ , X ² and X ³ are hydrogen atoms, R is not an alkyl group having from 1 to 2 carbon atoms.

A third object of the present invention is to provide an ultraviolet absorbent containing one or more compounds of the following general formula (I).

Wherein A is a group represented by the following formula;

인 경우, R은 1 내지 2개 탄소원자를 갖는 알킬기가 아니며, A가

이고 또 X¹, X²및 X³이 수소원자인 경우, R은 1 내지 2개 탄소원자를 갖는 알킬기가 아님.Wherein B represents a hydrogen atom or an acetyl group; W represents a hydrogen atom or -CH ₂ -CH ₂ -CO-OR; Y represents an oxygen atom or an imino group (-NH-); Z represents a methyl group or a phenyl group; And R represents a straight chain alkyl group having 1 to 18 carbon atoms, or a branched or cyclic alkyl group having 3 to 18 carbon atoms; X ¹ , X ² and X ³ independently represent a hydrogen atom, a hydroxyl group or a methoxyl group (two or three of which may be the same or both may be different); With A

When R is not an alkyl group having 1 to 2 carbon atoms, A is

And when X ¹ , X ² and X ³ are hydrogen atoms, R is not an alkyl group having from 1 to 2 carbon atoms.

The general formula (I) compound according to the present invention is a general formula (I) compound in which A is a group of general formula (II), that is, a compound represented by the following general formula (IV) and A is a group of general formula (III) I) can be roughly classified into compounds, ie, compounds represented by the following general formula (V), all of which are novel compounds.

In formula (IV), B is a hydrogen atom or an acetyl group; X ¹ , X ² and X ³ are each a hydrogen atom, a hydroxyl group or a methoxyl group; Y is an oxygen atom or an imino group (-NH-); Z is a methyl group or a phenyl group; And R is a straight, branched or cyclic alkyl group having 3 to 18 carbon atoms; In the formula (V), X ¹ and X ³ are a hydrogen atom or a methoxyl group; X ² is a methoxyl group or a hydroxyl group; W is hydrogen atom or -CH ₂ -CH ₂ -COOR; And R is a straight chain alkali having 1 to 18 carbon atoms, or a branched or cyclic alkyl group having 3 to 18 carbon atoms; Or X ¹ , X ² and X ³ are hydrogen atoms; W is hydrogen atom or -CH ₂ -CH ₂ -COOR; And R is a straight chain, branched chain or cyclic ring group having 3 to 18 carbon atoms.

Preferred compounds of the invention are as follows: B is a hydrogen atom or acetyl; X ¹ and X ³ are hydrogen atoms or methoxyl groups; X ² is a methoxyl group or a hydroxyl group; Y is an oxygen atom or an imino group; R is isopropyl group, n-butyl group, isobutyl group, amyl group, isoamyl group, n-hexyl group, cyclohexyl group, n-octyl group, 2-ethylhexyl group, 2, 2, 4-trimethyl The compound represented by general formula (IV) which is a cyclohexyl group, a decyl group, a lauryl group, a myristyl group, a cetyl group, or a stearyl group. X ¹ and X ² are methoxyl groups; X ³ is a hydrogen atom; W is hydrogen atom or -CH ₂ -CH ₂ -CO-OR; R is methyl, ethyl, isopropyl, n-butyl, isobutyl, amyl, isoamyl, n-hexyl, cyclohexyl, n-octyl, 2-ethylhexyl, 2, 2 A compound represented by the general formula (V) which is a 4-trimethylcyclohexyl group, a decyl group, a lauryl group, a myristyl group, a cetyl group, or a stearyl group, and X ¹ , X ² and X ³ are hydrogen atoms; W is hydrogen atom or -CH ₂ -CH ₂ CO-OR; R is isopropyl group, n-butyl group, isobutyl group, amyl group, isoamyl group, n-hexyl group, cyclohexyl group, n-octyl group, 2-ethylhexyl group, 2, 2, 4-trimethyl The compound represented by general formula (IV) which is a cyclohexyl group, a decyl group, a lauryl group, a myristyl group, a cetyl group, or a stearyl group.

More preferred compounds of the present invention are as follows: B is a hydrogen atom or an acetyl group; X ¹ and X ³ are hydrogen atoms; X ² is a methoxyl group; Y is an oxygen atom or an amino group (-NH-); Z is a methyl group or a phenyl group; And R is a compound represented by formula (IV) wherein isopropyl, 2-ethylhexyl, lauryl, isostearyl, cyclohexyl or a 3, 3, 5-trimethylcyclohexyl group. X ¹ and X ² are methoxyl groups and X ³ is a hydrogen atom; W is hydrogen atom or -CH ₂ CH ₂ COOR; And R is a compound represented by the formula (V) which is methyl, ethyl, n-butyl, isobutyl or 2-ethylhexyl group, and X ¹ , X ² and X ³ are hydrogen atoms; W is a hydrogen atom; And R is a compound represented by formula (V) wherein n-butyl, isobutyl or 2-ethylhexyl group.

The compound represented by general formula (IV) can be manufactured by the following method. (1) In the presence of a basic catalyst, the aromatic aldehyde of the general formula (VI) shown below (i-1) the acetylglycine or benzoylglycine of the general formula (VII) shown below or (i-2) the general formula shown below Condensation with the azlactone precursor of (IX) and (ii-1) hydrolyzing the resulting alactone compound represented by the general formula (VIII) shown below, followed by esterification or amidation. Or (ii-2) direct alcohol degradation or amino decomposition of the resulting alactone represented by the general formula (VIII) shown below, and (iii) acetylation of the nitrogen atom of the amide, if necessary. (2) The α-keto acid or ester of the general formula (X) shown below is condensed with an imine or amide of the phosphine of the general formula (XI) shown below. (3) N-hydroxyamino ester of the general formula (XII) shown below is reacted with a compound of the general formula (XII) shown below, and the resulting N-hydroxyamino acid ester of the general formula (XIV) Dehydrate.

The reaction schemes in the above-mentioned production methods (1)-(3) are as follows.

Method (1)

If the acetylation reaction proceeds further:

(iii) a compound of formula (I ')

[Compound of General Formula (IV), wherein B = H]

Wherein X ¹ , X ² , X ³ , Y, Z and R are as defined above.

Method (2)

Wherein X ¹ , X ² , X ³ , Y, Z and R are as defined above.

Method (3)

Wherein X ¹ , X ² , X ³ , Y, Z and R are as defined above.

In process (1), the condensation reaction with the aromatic aldehyde of formula (VI) and acetylglycine or benzoylglycine of formula (VII) in the presence of a basic catalyst is carried out at a temperature of 0 to 150 ° C.

In the presence of a basic catalyst, the condensation reaction with the aromatic aldehyde of formula (VI) and the azlactone precursor of formula (IX) is carried out at a temperature of 70 to 150 ° C. Basic catalysts include amines such as piperidine and triethylamine; Metal alcoholates such as sodium alcoholate, potassium alcoholate and the like; Sodium acetate, butyl lithium, sodium hydroxide, potassium hydroxide and the like.

Hydrolysis of the resulting azlactone compound represented by formula (VIII) is carried out at a temperature of 10 to 150 ℃. The esterification or amidation of the hydrolyzed compound is carried out at a temperature of 0 to 150 ° C.

The alcohol decomposition reaction of the azlactone compound represented by the general formula (VIII) is preferably carried out using a basic catalyst such as metal alcoholate (e.g., sodium alcoholate, potassium alcoholate, etc.), sodium hydroxide, potassium hydroxide, or the like. It is carried out at a temperature of 10 to 150 ℃. The acetylation reaction of the amide nitrogen atom in the compound of formula (I ') is preferably carried out at a temperature of -30 to 150 ° C using a catalyst such as dimethylaminopyridine, pyrrolidinopyridine and the like.

In process (2), the condensation reaction of α-keto acid or ester of general formula (X) with an amine or amine of phosphine of general formula (XI) is carried out at a temperature of -30 to 150 ° C.

In method (3), the reaction of the N-hydroxyamino ester compound of formula (XII) and the compound of formula (XIII) is -30 to 150 in the presence of a catalyst such as pyridine, dimethylaminopyridine and pyrrolidinopyridine. It is carried out at a temperature of ℃.

II. The compound represented by general formula (V) may be prepared by the following method:

Condensation of the aromatic aldehyde of formula (VI) and hydantoin of formula (XV) in the presence of a basic catalyst; Furthermore, the Michael addition reaction of the acrylic ester of general formula (XVII) is carried out to the obtained benzalhydantoin of general formula (XVI).

The reaction scheme in the production method is as follows.

Wherein X ¹ , X ² , X ³ and R are as defined above.

The condensation reaction of the aromatic aldehyde of general formula (VI) with hydantoin of general formula (XV) is carried out at a temperature of 0 to 150 ° C. Basic catalysts include amines such as piperidine and triethylamine; amino acid; Aqueous ammonia solution; Metal alcoholates such as sodium alcoholate, potassium alcoholate and the like; Sodium acetate, sodium hydroxide, potassium hydroxide and the like are used.

The reaction for producing the benzalhydantoin of the general formula (XVI) by adding the Michael ester of the acrylic ester of the general formula (XVII) is carried out at a temperature of 20 to 200 ℃.

The following are examples of compounds of general formula (IV) according to the invention:

N-benzoyl-O-methyl-α-dehydrotyrosine laurylamide, N-benzoyl-O-methyl-α-dehydrotyrosine isopropyl ester, N-benzoyl-O-methyl-α-dehydrotyrosine lauryl ester , N-benzoyl-O-methyl-α-dehydrotyrosine stearyl ester, N-benzoyl-O-methyl-α-dehydrotyrosine-2-ethylhexyl ester, N-benzoyl-O-methyl-α-dehydro Tyrosinecyclohexyl ester, N-benzoyl-O-methyl-α-dehydrotyrosine 3, 3, 5-trimethylcyclohexyl ester, N-acetyl-O-methyl-α-dehydrotyrosine isopropyl ester, N-acetyl- O-methyl-α-dehydrotyrosine 2-ethylhexyl ester, N-acetyl-O-methyl-α-dehydrotyrosine lauryl ester, N-acetyl-O-methyl-α-dehydrotyrosine 2-stearyl ester , N-acetyl-N-benzoyl-O-methyl-α-dehydrotyrosine isopropyl ester, N-acetyl-N-benzoyl-O-methyl-α-dehydrotyrosine 2-ethylhexyl ester, N-acetyl-N-benzoyl-O-methyl-α-dehydrotyrosine lauryl ester, N-acetyl-N-benzoyl-O-methyl-α-dehydrotyrosine stearyl ester, N, N-diacetyl-O -Methyl-α-dehydrotyrosine isopropyl ester, N, N-diacetyl-O-methyl-α-dehydrotyrosine 2-ethylhexyl ester, N, N-diacetyl-O-methyl-α-dehydrotyrosine Lauryl ester, N, N-diacetyl-O-methyl-α-dehydrotyrosine stearyl ester, N-acetyl-N-benzoyl-O-methyl-α-dehydrotyrosine n-butyl ester, N, N- Diacetyl-O-methyl-α-dehydrotyrosine n-butyl ester, and N-benzoyl-3, 4, 5-trimethoxy-α-dehydrophenylalanine 2-ethylhexyl ester.

Examples of general formula (V) compounds according to the invention:

Diisopropyl 4-benzylidene-2, 5-dioxo-1, 3-imidazolidine dipropionate, di-n-butyl-4-benzylidene-2, 5-dioxo-1, 3- Imidazolidine dipropionate, diisobutyl 4-benzylidene-2, 5-dioxo-1, 3-imidazolidine dipropionate, bis (2-ethylhexyl) 4-benzylidene-2 , 5-dioxo-1, 3-imidazolidine dipropionate, isopropyl 4-benzylidene-2, 5-dioxo-1-imidazolidine propionate, n-butyl 4-benzylidene -2,5-dioxo-1-imidazolidine propionate, isobutyl 4-benzylidene-2, 5-dioxo-1-imidazolidine propionate, 2-ethylhexyl 4-benzylidene -2,5-dioxo-1-imidazolidine propionate, dimeltyl 4- (3,4-dimethoxyphenyl) methylene-2, 5-dioxo-1, 3-imidazolidine diprop Cypionate, Diethyl 4- (3, 4-dimethoxyphenyl) -methylene-2, 5-dioxo-1, 3-imidazolidine dipropionate, diisopropyl 4- (3, 4-dimeth Cyphenyl) methylene-2, 5-dioxo-1, 3-imidazolidine dipropionate, di-n-butyl 4- (3,4-dimethoxyphenyl) methylene-2, 5-dioxo- 1, 3-imidazolidine dipropionate, diisobutyl 4- (3,4-dimethoxyphenyl) methylene-2, 5-dioxo-1, 3-imidazolidinedi propionate, bis ( 2-ethylhexyl) 4- (3,4-dimethoxyphenyl) methylene-2, 5-dioxo-1, 3-imidazolidinedipropionate, isopropyl 4- (3, 4-dimethoxyphenyl Methylene-2, 5-dioxo-1-imidazolidine propionate, methyl 4- (3,4-dimethoxyphenyl) methylene-2, 5-dioxo-1-imidazolidine propionate Ethyl 4- (3,4-dimethoxyphenyl) methylene-2,5-dioxo-1-imidazolidine propionate, n-butyl 4- (3,4-dimethoxyphenyl) methylene-2, 5-dioxo-1-imidazolidine propionate, isobutyl 4- (3,4-dimethoxyphenyl) methylene-2, 5-dioxo-1-imidazolidine propionate, 2-ethyl Hexyl 4- (3, 4- Methoxyphenyl) methylene-2, 5-dioxo-1-imidazolidine propionate, ethyl 4- (4-methoxyphenyl) methylene 2, 5-dioxo-1-imidazolidine propionate And ethyl 4- (3, 4, 5-trimethoxyphenyl) methylene-2, 5-dioxo-1-imidazolidine propionate.

Cosmetic compositions according to the invention are generally used in cosmetic compositions such as compounds represented by general formula (I) and oily components, aqueous phase components, powder components and / or surfactant components which emulsify, disperse or dissolve these component substances. It consists of known components.

Examples of known components that can be used in the composition of the present invention are as follows.

As an oily ingredient, beeswax, wax, whale wax, carnauba wax, candela wax, cacao oil, cetyl alcohol, stearyl alcohol, oleic acid, stearic acid, lanolin, olive oil, tsubaki oil, cottonseed oil, castor oil, Animal or vegetable oils such as oleyl alcohol, squalane and the like; Mineral oils and fats such as solid paraffin, ceresin, microcrystalline wax, petrolatum, liquid paraffin, silicone oils and the like; Synthetic oils and fats such as isopropyl myristate, synthetic polyether, and the like.

As an aqueous phase component, glycerin, propylene, glycol, sorbitol, polyethylene glycol, queen seed gum, tragacanth rubber, alginic acid, pectin, carboxymethyl cellulose, hyaluronic acid, water soluble chitin, polyvinyl alcohol, ethanol , Isopropanol, citric acid, urea, cationic cellulose fatty acid polyfabricated condensation products, lauric acid, pyrrolidone carboxylate and various types of amino acids. As the surfactant, polyoxyethylene fatty acid partial ester, polyoxyethylene sorbitan fatty acid partial ester, polyoxyethylene glycerin fatty acid partial ester, polyglycerol fatty acid partial ester, fatty acid alkanol amide, fatty acid alkanol amide-ethylene oxide addition product, Nonionic surfactants such as polyoxyethylene glycerin fatty acid, monoglycerine pyroglutamate, glycerin acyl glutamate, and the like; Alkyl sulfates, polyoxyethylene alkyl sulfates, fatty acid amide ether sulfates, alkyl benzene sulfates, alkoxy sulfonates, sulfosuccinic acid higher alcohol ester salts, N-long chain fatty acid acyl-N-methyl-taurine salts, fatty acid salts, Anionic surfactants such as N-long chain acyl glutamate, N-long chain acylsacosine salt, monoalkyl phosphate and the like; Amphoteric surfactants such as carboxybetaine type, imidazoline type, lecithin, aminosulfonic acid type, alkylamine oxite type, Nα, Nα-dimethyl or Nα, Nα, Nα-trimethyl-N-acyl basic amino acids; Cationic surfactants such as dialkyldimethyl ammonium chloride, alkyltrimethyl ammonium chloride, fatty acid acyl arginine ethyl ester salt and the like. Examples of the powder include inorganic powders such as talc, kaolin, titanium oxide, titanium-coated mica, mica, iron oxide, ultramarine silicate, prussian blue, galvanized, clay and precipitated calcium carbonate; And organic powders such as N-long chain acyl basic amino acids.

The cosmetic composition of the present invention further contains a thickening agent, a softener, a humectant, a hyperfatting agent, a relaxing agent, a preservative, an antifoaming agent, a perfume, the composition itself or other substances commonly used in cosmetics such as dyes for coloring the skin. can do.

Cosmetic compositions of the present invention can be prepared in the required form, such as solutions, emulsions, dough mixtures, solids (compressed formulations), powders, etc. by appropriately selecting and adjusting the type and amount of ingredients to be mixed. Uses of the cosmetic composition of the present invention include sun oil, lotion, cream, milk lotion, hair conditioner, hair conditioner, liquid foundation, lipstick, foundation, powder, aerosol and the like.

The content of the compound of general formula (I) in the cosmetic composition of the present invention varies depending on the mixed components and the aging of the sun protection index (SPF), but the content is usually 0.1 to 20% by weight, preferably 0.5 to 10% by weight. to be.

As the ultraviolet absorber to be contained in the cosmetic composition of the present invention, one of the compounds represented by the general formula (I) may be used alone or in combination of two or more of these compounds. In addition, one or more of the compounds of the general formula (I) may be used in combination with other types of ultraviolet absorbers.

Other ultraviolet absorber types that can be used in admixture with the compound of formula (I) include camphor derivatives such as P-methylbenzylidene-D, L-camphor or sodium sulfonates thereof; Benzophenones such as sodium 2-phenylbenzimidazole-5-sulfonate, sodium 3, 4-dimethylphenylglyoxylate, isooctyl 4-phenylbenzophenone-2-carboxylate and the like; And P-methoxycinnamic acid ester, 2-phenyl-5-methylbenzooxazole, 2-ethylhexyl salicylate, P-dimethylaminobenzoic acid ester, and the like.

They can also be used with inorganic powders such as titanium oxide, which act as a diffusing agent.

The compound represented by formula (I) used in the present invention has a high molecular extinction coefficient of 10 ⁴ or more at 270-320 nm. These compounds also have high UV absorption at 290-320 nm wavelengths that cause skin erythema and 300-320 nm wavelengths that cause degradation of resins such as polyethylene, polypropylene, polyvinyl chloride, and the like. In addition, the compounds of general formula (I) are, for example, due to the influence of R when compared to known compounds such as N-benzoyl-α-dihydrotyrosine and O-methyl-N-benzoyl-α-dihydrotyrosine. Solubility in various kinds of animal and vegetable oils, fats and oils and organic solvents is significantly improved. In addition, compounds of formula (I) in which the hydrogen atom of the amide is substituted with an acetyl group have much better solubility in various types of animal and vegetable oils, fats and oils and organic solvents.

Therefore, the compound of general formula (I) can be well dissolved in various kinds of animal and vegetable oils, fats and fats and other organic solvents, and can also be used in creams, milk lotions, foundations, hair creams and sunscreen oils (anti-sunburn oils). It can provide a stable composition when added to cosmetic preparations such as antisunburn oil. In addition, when these compounds are added to resins such as polyethylene, polypropylene, polystyrene, polyvinyl chloride, ABS resin, polycarbonate and the like, the compound of the present invention has good compatibility with these resins. The α-dihydroamino acid derivatives of general formula (IV) used in the present invention have the following advantages when compared to commercially available ultraviolet absorbers (e.g., benzophenone UV absorbers, triazole UV absorbers and salicylic acid UV absorbers). Have. (1) The inhibitory effect of these derivatives on ultraviolet light is particularly excellent in the presence of oxygen. (2) These derivatives have excellent thermal and light stability and these effects last long. (3) These derivatives have UV molecular absorption coefficients that are 2 to 10 times higher than commercial UV absorbers. (4) Since compatibility with various polymer materials is good, these derivatives can be used as plasticizers for fibers, resins, etc., and can also be used as yellowing inhibitors.

As described above, the compounds of the present invention have a wide range of uses and fields of use, including the perfume and cosmetics industry, the plastics industry, the organic drug industry, the photography industry, the food industry and the textile industry.

In particular, since the compound of the present invention has an ultraviolet absorption of 240-360nm (maximum absorption wavelength: 300-340nm) wavelength, when the compound is used in cosmetics, it provides an anti-sunburn and anti-erythema cosmetics having various selective UV absorption do. In addition, when these compounds are mixed in a polymer such as polyethylene, polypropylene, polyvinyl chloride, or the like, the degradation of the polymer due to ultraviolet rays is significantly reduced.

Compounds represented by the general formula (V), in particular, compounds of the general formula (V) wherein X ² is a hydroxyl or methoxyl group, have high absorption of long wavelength (320-400 nm) ultraviolet rays and various kinds of animal and vegetable oils, fats and It is also dissolved in fats and oils and organic solvents.

Compounds represented by formula (I) are highly UV absorbing, have excellent light and thermal stability and are non-irritating and non-harmful to skin, hair, mucous membranes and other tissues of the human body. When a suitable amount (selected within the range of 0.1 to 20% by weight) is formulated in various kinds of cosmetic preparations such as milk lotion, hair rinse, hair conditioner, liquid foundation, lipstick, foundation, powder, aerosol, etc. Cosmetic preparations are found to be excellent in ultraviolet absorption and stable to light and heat.

Typical examples of the compounds according to the invention, and the maximum absorption wavelengths (UV wavelengths in which the compounds exhibit the maximum UV absorbance) and other properties measured as typical examples of the compounds according to the invention are shown in Example 1 in Tables 1 and 2 below. Indicates. The solubility of the compound in the organic solvent is shown in Example 3 in Table 3, and representative examples of the formulation using the compound of the present invention are shown in Examples 11 to 23. However, the present invention is not limited to these examples.

Example 1

TABLE 1a

TABLE 1b

Example 1

TABLE 2a

Characteristic values of α-dehydroamino acid derivative represented by formula (IV)

TABLE 2b

Characteristic Values of Benzyl Hydantoin Derivatives of Formula (V)

Example 2

Synthesis Example 1

Synthesis of 2-phenyl-4- (4-methoxybenzylidene) -5-oxazolone

20 ml of anisealdehyde, 50 ml of acetic anhydride, 33.7 g of hypuric acid and 6.7 g of sodium acetate are mixed well and heated for 30 minutes on a water bath. The precipitated crystals are washed with hot water and then filtered. They are then recrystallized from benzene and dried to yield 40 g of 2-phenyl-4- (4-methoxybenzylidene) -5-oxazolone. Yield 83%.

Synthetic Example 2

Synthesis of N-benzoyl-O-methyl-α-dehydrotyrosine 2-ethylhexyl ester

1 kg of 2-phenyl-4- (4-methoxybenzylidene) -5-oxazolone obtained in Synthesis Example 1 was suspended in 10 liter toluene, followed by 0.933 kg 2-ethyl-1-hexanol and 0.029 kg Sodium hydroxide is added. The mixture is stirred at 25 ° C. for 4 hours, followed by the addition of 40 liters of ethyl acetate and 40 liters of water, followed by further stirring of the mixture. The organic layer is separated, dried over forget-me-not and concentrated under reduced pressure. This residue is recrystallized from toluene-hexane to yield 1.0 kg of N-benzoyl-O-methyl-α-dehydrotyrosine 2-ethylhexyl ester (yield: 68.2%).

Example 3

Synthesis of N-benzoyl-O-methyl-α-dehydrotyrosine n-lauryl ester

2 g of sodium metal is added to 154 ml of n-lauryl alcohol and dissolved under heating. 118.6 g of 2-phenyl-4- (4-methoxybenzylidene) -5-oxazolone obtained in Synthesis Example 1 and 300 ml of toluene are added to this solution, and the mixture is stirred at 25 ° C. for 8 hours. . The resulting reaction solution is added to 2 liters ethyl acetate and washed with 1.5 liters IN hydrochloric acid, 1.5 liters 5% sodium bicarbonate salt and 1.5 liters water, then dried over forget-me-not and concentrated under reduced pressure. This residue was recrystallized from n-hexane to give 163.5 g of N-benzoyl-O-methyl-α-dehydrotyrosine n-lauryl ester (yield: 82.7%).

Example 4

Synthesis of N-acetyl-N-benzoyl-O-methyl-α-dehydrotyrosine n-lauryl ester

10 g of N-benzoyl-O-methyl-α-dehydrotyrosine n-lauryl ester obtained in Example 3 is dissolved in 100 ml pyridine, followed by addition of 20 ml acetic anhydride and 0.5 g dimethylaminopyridine, and the mixture is Stir at 25 ° C. for 14 hours. The reaction solution is concentrated under reduced pressure and the residue is dissolved in 300 ml ethyl acetate. The solution is washed four times with 250 ml water and concentrated again under reduced pressure. The residue was separated by silica gel column chromatography to obtain 8.8 g (yield: 81.1%) of N-acetyl-N-benzoyl-O-methyl-α-dehydrotyrosine n-lauryl ester.

Example 5

Synthesis of n-butyl 4- (2,3-dimethoxyphenylmethylene) 2,5-dioxo-1-imidazolidinepropionate

20 g (80,6 mmol) of 5- (2,3-dimethoxybenzylidine) hydantoin, 12.4 g (96 mmol) of n-butylacrylate and 0.90 g (1.6 mmol) of potassium hydroxide were added to 150 ml dimethylformamide And the mixture is stirred at 110 ° C. for 2 hours. 200 ml of water is added to the reaction solution, followed by extraction with 500 ml of ethyl acetate. The extract is dried over sodium sulfate and then the solvent is distilled off under reduced pressure. Toluene was added to the residue and the precipitated crystals were dried to give 24.7 g of n-butyl 4- (2,3-dimethoxyphenylmethylene) -2,5-dioxo-1-imidazolidine propionate (yield) : 81.5%).

Example 6

Synthesis of 2-ethylhexyl 4- (2,3-dimethoxyphenylmethylene) -2,5-dioxo-1-imidazolidine propionate

20 g (86.6 mmol) 5- (2,3-dimethoxybenzylidene) hydantoin, 17.8 g (96 mmol) of 2-ethylhexyl acrylate and 0.90 g (1.6 mmol) of potassium hydroxide are added to 150 ml dimethylformamide, The mixture is stirred at 110 ° C. for 2 hours. After cooling, 200 ml of water was added to the reaction solution, followed by extraction with 500 ml of ethyl acetate. The extract is dried over sodium sulfate and the solvent is then distilled off under reduced pressure. The residue was recrystallized with toluene-n-hexane (1: 1), and the precipitated crystals were dried to give 2-ethylhexyl 4- (2,3-dimethoxyphenyl methylene) -2,5-dioxo-1-imide 27.1 g (yield: 77.8%) of dazolidinepropionate are obtained.

Example 7

Synthesis of diethyl 4- (2, 3-dimethoxyphenylmethylene) -2, 5-dioxo-1, 3-imidazolidinedipropionate

20 g (80.6 mmol) of 5- (2,3-dimethoxybenzylidene) hydantoin, 17.7 g (177 mmol) of ethyl acrylate and 0.90 g (1.6 mmol) of potassium hydroxide were added to 150 ml dimethylformamide (DMF) and The mixture is stirred at 110 ° C. for 2 hours. After cooling, 200 ml of water was added to the reaction solution, followed by extraction with 500 ml of ethyl acetate. The extract is dried over sodium sulfate and the solvent is distilled off under reduced pressure. The residue was separated and purified by silica gel column chromatography [eluent: toluene / ethyl acetate (3/1)] to give diethyl 4- (2, 3-dimethoxyphenylmethylene) -2, 5-dioxo-1, 22.5 g (yield: 62.3%) of 3-imidazolidinedipropionate are obtained.

Example 8

Synthesis of Isobutyl 4-benzylidene-2, 5-dioxo-1-imidazolidinepropionate

20 g (0.106 mol) of benzylhydrantoin, 14.9 g (0.117 mol) of isobutyl acrylate and 1.2 g (0.02 mol) of potassium hydroxide are added to 150 ml DMF and the mixture is stirred at 110 ° C. for 2 hours. After cooling, 300 ml toluene was added to this reaction solution and crystallized. The crystals were filtered and dried to yield 27.2 g of isobutyl 4-benzylidene-2, 5-dioxo-1-imidazolidinepropionate (a ratio: 81%).

Example 9

Synthesis of bis (2-ethylhexyl) 4-benzylidene-2, 5-dioxo-1, 3-imidazolidinedipropionate

10 g (53.1 mmol) benzalhydantoin, 23.6 g (127.6 mmol) 2-ethylhexyl acrylate and 0.6 g (10.6 mmol) potassium hydroxide are added to 100 ml DMF and the mixture is stirred at 110 ° C. for 2 hours. After cooling, the reaction solution is extracted with ethyl acetate and the organic layer is washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue is dissolved in toluene and crystallized by addition of hexane. The crystals were filtered and dried to yield 19.8 g of bis (2-ethylhexyl) 4-benzylidene-2, 5-dioxo-1, 3-imidazolidinepropionate (yield: 42.3%).

Example 10

TABLE 3

Solubility of the novel α-dehydroamino acid derivative represented by formula (IV).

( ^* 1) Grams of sample dissolved in 100 ml solvent.

Example 11

Sun oil

Sun oil is prepared by mixing the materials shown below in the indicated amounts. The more favorable conditions for homogenizing the next composition are mixing the materials while heating at about 40-45 ° C.

4% by weight of N-benzoyl-O-methyl-α-dehydrotyrosine isostearyl

Ester (Compound No. 4)

2.5% by weight of cacao oil

Perfume 0.5% by weight

93% by weight of fatty acid triglycerides (C ₈ -C ₁₂ )

Example 12

Skin protection cream (O / W type)

Components (A) and (B) according to the following formulations are respectively dissolved under heating, and these are mixed and cooled to room temperature to prepare a skin protection cream.

(A)

Diethyl 4- (3,4-dimethoxyphenyl) methylene-2, 5-dioxo-1, 3-di 8% by weight

Midazolidinedipropionate (Compound No. 19)

N-benzoyl-O-methyl-α-dehydrotyrosine-3, 3, 5-trimethyl 8% by weight

Cyclohexyl ester (compound number 16)

10% by weight of fatty acid triglycerides (C ₈ -C ₁₂ )

Cetyl alcohol 1.5% by weight

6% by weight of polyoxyethylene cetyl ether and polyoxyethylene stearyl ether

(10 ethylene oxide)

2% by weight of polyoxyethylene sorbitan mono stearate (20 ethylene oxide)

(B)

Glycerin 1.5% by weight

Propylene Glycol 1.5 wt%

Sorbitol solution (70%) 3.5 wt%

Sodium pyrrolidonecarboxylate 0.5% by weight

0.2 wt% of methyl para-oxybenzoate

57% by weight of water

Example 13

Skin Protection Cream (W / O Type)

The following ingredients were mixed and treated in the same manner as in Example 12 to prepare a skin protection cream.

(A)

N-benzoyl-O-methyl-α-dehydrotyrosine 2-ethylhexyl 8% by weight

Ester (Compound No. 2)

Cetyl alcohol 1.5% by weight

Beeswax 1.5 wt%

3% by weight of paraffin oil

1% by weight cholesterol

8% by weight of fatty acid triglycerides (C ₈ -C ₁₂ )

5% by weight glycerin monostearate

9% by weight of sorbitan monopalmitate

1% by weight of polyoxyethylene sorbitan monostearate (20 ethylene oxide)

Ceresin 5% by weight

Whale wax 2% by weight

0.1% by weight of propyl para-oxybenzoate

(B)

Glycerin 1.5% by weight

Propylene Glycol 1.5 wt%

4% by weight of sorbitol solution (70%)

0.2 wt% of methyl para-oxybenzoate

47.7% by weight of water

Example 14

Sun Oil (Milk Lotion)

The following ingredients were mixed and treated in the same manner as in Example 12 to prepare sun oil.

(A)

2-ethylhexyl 4-benzylidene-2, 5-dioxo-1-imidazolidineprop 5% by weight

Cypionate (Compound No. 13)

2-ethylhexyl 4- (3,4-dimethoxyphenyl) methylene-2,5-dioxo-2% by weight

1-imidazolidine propionate (Compound No. 18)

Polyoxyethylene cetyl ether and stearyl ether (5% by weight of 10 ethylene

Oxide)

6% by weight of petrolatum oil

Isopropyl myristate 8% by weight

1% by weight of silicone oil

1% by weight of cetyl alcohol

Preservative

Perfume

Water rest

Example 15

Sun Milk (Milk Lotion)

The following ingredients were mixed and treated in the same manner as in Example 12 to prepare sun milk.

(A)

5% by weight of isobutyl 4-benzylidene-2, 5-dioxo-1-imidazolidineprop

Cypionate (Compound No. 12)

22.6% by weight of liquid paraffin

4.5 wt% of solid paraffin

Cetanol 4% by weight

Sorbitan monostearate 1.8% by weight

Polyoxyethylene sorbitan monostearate (2.8 wt% of 20 ethylene

Oxide)

5% by weight of N _δ -cocoyl ornithine

(B)

Triethanolamine pyrrolidone carboxylate 4% by weight

50.1% by weight of water

Preservative 0.2% by weight

Example 16

Antisunburn lotion

According to the following formulation, component (A) is dissolved under heating and cooled to room temperature, and then component (B) is added to prepare antisunburn lotion.

(A)

2% by weight to N-benzoyl-O-methyl-α-dehydrotyrosine cyclohexyl

Stear (Compound No. 5)

Glycerin 5% by weight

Polyethylene Glycol 400 0.5 wt%

Perfume

Water rest

(B)

96% ethanol 40% by weight

Example 17

lipstick

The lipstick is prepared according to the following formulation. A part of (B) is added to (A), and the mixture is rolled to prepare a pigment powder. The thermally dissolved component (B) is then added and the mixture is homogenized and immediately cooled to solidify and then molded.

(A)

Titanium Dioxide 2% by weight

N-benzoyl-O-methyl-α-dehydrotyrosine isopropyl 5.7 weight

Ester (Compound No. 1)

(B)

25% by weight of hexadecyl alcohol

4% by weight lanolin

5% by weight of beeswax

4% by ozoselite

Candela wax 7% by weight

Carnauba wax 2% by weight

Appropriate amount of antioxidant

Perfume

Castor Oil Rest

Example 18

Oily Sun Gel

Fatty materials according to the following formulations are heated to 40-45 ° C. to dissolve, then silica is added under stirring and the mixture is cooled to prepare an oily sun gel.

3% by weight of N-benzoyl-O-methyl-α-dehydrotyrosine lauryl S

Ter (compound number 3)

2-ethylhexyl P-methoxycinnamate 2% by weight

2.5% by weight of cacao fat

10 wt% silica

Appropriate amount of antioxidant

Perfume

Fatty acid triglycerides (C ₈ -C ₁₂ )

Example 19

Effervescent air spray

90 parts of the mixture of the following composition and 10 parts of Freon gas (F21 / F114 = 40/60) were charged to a pressure vessel to prepare a foamed air spray.

0.3% by weight of N-acetyl-N-benzoyl-O-methyl-α-dehydrotyrosine lauryl

Ester (Compound No. 7)

7% by weight stearic acid

Propylene glycol 7% by weight

6% by weight of triethanolamine

2% by weight of olive oil

Water rest

Example 20

Non-foaming lotion air spray

30 parts of the mixture of the following composition and 70 parts of Freon gas (F21 / F114 = 40/60) were charged to a pressure vessel to prepare a non-foamable lotion air spray.

1% by weight N-acetyl-O-methyl-α-dehydrotyrosine isopropyl

Ester (Compound No. 8)

10% by weight of propylene glycol

30% by weight 99% ethanol

Water rest

Example 21

Foundation

The component (C) according to the following formulation (oil phase) is mixed and dissolved by heating at 70 ° C (oil phase). Separately, the component (B) is mixed, dissolved and stored at 70 ° C (water phase). The component (A) is dispersed in an aqueous phase, emulsified by adding an oil phase, and then cooled to prepare a mixture.

(A)

N-butyl 4-benzylidene-2, 5-dioxo-1-imidazolidine 10% by weight

Propionate (Compound No. 11)

Titanium oxide 6% by weight

1.5 wt% red iron oxide

Iron sulfur 0.2% by weight

(B)

Monomagnesium N-lauroyl glutamate 0.5 wt%

1.4% by weight of triethanolamine

Propylene Glycol 9.5 wt%

37.9 weight% of water

(C)

2.8% by weight stearic acid

Propylene Glycol Monostearate 2.8 wt%

Glycerin monostearate (self-emulsifying) 2.8 wt%

24.6% by weight liquid paraffin

Example 22

Percentage

The materials according to the following formulations are mixed to obtain a powder.

N-benzoyl-O-methyl-α-dehydrotyrosine lauryl 72.4 wt%

Amide (Compound No. 10)

Talc 10% by weight

Titanium oxide 1 wt%

5% by weight kaolin

N _ε -5% by weight of laurolysine

Zinc laurate 1.8% by weight

Iron oxide (red, yellow and black) 1.8% by weight

3% by weight of perfume

Example 23

Rinse

Component (A) according to the following formulation is mixed and dissolved by heating at 80 ° C., and then (B) is added and dispersed. (C) dissolved at 80 DEG C is added to this dispersion, and the solution is mixed and emulsified and then cooled to room temperature to prepare a rinse.

(A)

1% by weight N-acetyl-O-methyl-α-dehydrotyrosine isopropyl

Ester (Compound No. 8)

1% by weight of cationic DS (manufactured by Sanyo Chemical Industries, Inc.)

0.5% by weight of CAE (product of Ajino Moto Corporation)

0.5 wt% polyoxyethylene sorbitan monooleate (4 ethylene oxide)

0.5 wt% polyoxyethylene sorbitan monooleate (25 ethylene oxide)

80.5% by weight of water

(B)

N _ε -2% by weight of laurolysine

(C)

2% by weight of liquid paraffin

Cetanol 3% by weight

Claims (30)

Benzylidene compound represented by the following general formula (I):

Wherein A is a group represented by the following formula;

Wherein B represents a hydrogen atom or an acetyl group; W is hydrogen atom or -CH ₂ -CH ₂ -CO-OR; Y represents an oxygen atom or an imino group (-NH-); Z represents a methyl group or a phenyl group; R represents a straight chain alkyl group having 1 to 18 carbon atoms, or a branched or cyclic alkyl group having 3 to 18 carbon atoms; X ¹ , X ² and X ³ independently represent a hydrogen atom, a hydroxyl group or a methoxyl group (two or three of which may be the same or both may be different); With A

R is not an alkyl group having 1 to 2 carbon atoms, and A is

And when X ¹ , X ² and X ³ are hydrogen atoms, R is not an alkyl group having from 1 to 2 carbon atoms. The compound of claim 1 wherein A is

ego; B is a hydrogen atom or an acetyl group; X ¹ , X ² and X ³ are hydrogen atom, hydroxyl group or methoxyl group; Y is an oxygen atom or an imino group (-NH-); Z is a methyl group or a phenyl group; And R is a straight, branched or cyclic alkyl group having 3 to 18 carbon atoms. The compound of claim 1 wherein A is

ego; X ¹ and X ³ are hydrogen atoms or methoxyl groups; X ² is a methoxyl group or a hydroxyl group; W is hydrogen atom or -CH ₂ -CH ₂ -COOR; And R is a linear alkyl group having 1 to 18 carbon atoms or a branched or cyclic alkyl group having 3 to 18 carbon atoms. The compound of claim 1 wherein A is

ego; X ¹ , X ² and X ³ are hydrogen atoms; W is a hydrogen atom or -CH ₂ -CH ₂ -COOR, and R is a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms. 3. A compound according to claim 2, wherein B is a hydrogen atom or an acetyl group; X ¹ and X ³ are hydrogen atoms or methoxyl groups; X ² is a methoxyl group or a hydroxyl group; Y is an oxygen atom or an imino group; R is isopropyl group, n-butyl group, isobutyl group, amyl group, isoamyl group, n-hexyl group, cyclohexyl group, n-octyl group, 2-ethylhexyl group, 2, 2, 4-trimethyl A compound which is a cyclohexyl group, a decyl group, a lauryl group, a myristyl group, a cetyl group, or a stearyl group. The compound of claim 3, wherein X ¹ and X ² are methoxyl groups; X ³ is a hydrogen atom; W is hydrogen atom or -CH ₂ -CH ₂ -CO-OR; R is methyl, ethyl, isopropyl, n-butyl, isobutyl, amyl, isoamyl, n-hexyl, cyclohexyl, n-octyl, 2-ethylhexyl, 2, 2 , 4-trimethylcyclohexyl group, decyl group, lauryl group, myristyl group, cetyl group or stearyl group. The compound of claim 4, wherein X ¹ , X ² and X ³ are hydrogen atoms; W is hydrogen atom or -CH ₂ -CH ₂ CO-OR-; R is isopropyl group, n-butyl group, isobutyl group, amyl group, isoamyl group, n-hexyl group, cyclohexyl group, n-octyl group, 2-ethylhexyl group, 2, 2, 4-trimethyl A compound which is a cyclohexyl group, a decyl group, a lauryl group, a myristyl group, a cetyl group, or a stearyl group. A compound according to claim 5, wherein B is a hydrogen atom or an acetyl group; X ¹ and X ³ are hydrogen atoms; X ² is a methoxyl group; Y is an oxygen atom or an imino group (-NH-); Z is a methyl group or a phenyl group; And R is isopropyl, 2-ethylhexyl, lauryl, isostearyl, cyclohexyl or a 3, 3, 5-trimethylcyclohexyl group. The compound of claim 6, wherein X ¹ and X ² are methoxyl groups; X ³ is a hydrogen atom; W is hydrogen atom or -CH ₂ CH ₂ COOR; And R is a methyl, ethyl, n-butyl, isobutyl, or 2-ethylhexyl group. 8. A compound according to claim 7, wherein X ¹ , X ² and X ³ are hydrogen atoms; W is hydrogen atom; And R is an n-butyl, isobutyl or 2-ethylhexyl group. An ultraviolet absorbent cosmetic composition containing an effective amount of the following general formula (I) compound:

Wherein A is a group represented by the following formula;

Wherein B is a hydrogen atom or an acetyl group; W is hydrogen atom or -CH ₂ -CH ₂ -CO-OR; Y is an oxygen atom or an imino group (-NH-); Z is a methyl group or a phenyl group; R is a straight chain alkyl group having 1 to 18 carbon atoms, or a branched chain or cyclic alkyl group having 3 to 18 carbon atoms; X ¹ , X ² and X ³ are independently a hydrogen atom, hydroxyl group or methoxyl group (two or three of which may be the same or both may be different); With A

R is not a hydrogen atom or an alkyl group having 1 to 2 carbon atoms, and A is

ego; And when X ¹ , X ² and X ³ are hydrogen atoms, R is not an alkyl group having from 1 to 2 carbon atoms. 12. The compound of claim 11 wherein A is

ego; B is a hydrogen atom or an acetyl group; Each X ¹ , X ² and X ³ is this hydrogen atom, a hydroxyl group or a methoxyl group; Y is an oxygen atom or an imino group (-NH-); Z is a methyl group or a phenyl group; And R is a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms. 12. The compound of claim 11 wherein A is

ego; X ¹ and X ³ are hydrogen atoms or methoxyl groups; X ² is a methoxyl group or a hydroxyl group; W is hydrogen atom or -CH ₂ -CH ₂ -COOR; And wherein R is a linear alkyl group having 1 to 18 carbon atoms or a branched or cyclic alkyl group having 3 to 18 carbon atoms. 12. The compound of claim 11 wherein A is

ego; X ¹ , X ² and X ³ are hydrogen atoms; W is hydrogen atom or -CH ₂ -CH ₂ -COOR; And wherein R is a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms. 13. A compound according to claim 12, wherein B is a hydrogen atom or an acetyl group; X ¹ and X ³ are hydrogen atoms or methoxyl groups; X ² is a methoxyl group or a hydroxyl group; Y is an oxygen atom or an imino group; R is isopropyl group, n-butyl group, isobutyl group, amyl group, isoamyl group, n-hexyl group, cyclohexyl group, n-octyl group, 2-ethylhexyl group, 2, 2, 4-trimethyl The ultraviolet absorbent cosmetic composition which is a cyclohexyl group, a decyl group, a lauryl group, a myristyl group, a cetyl group, or a stearyl group. The compound of claim 13, wherein X ¹ and X ² are methoxyl groups; X ³ is a hydrogen atom; W is hydrogen atom or -CH ₂ -CH ₂ -CO-OR; R is methyl, ethyl, isopropyl, n-butyl, isobutyl, amyl, isoamyl, n-hexyl, cyclohexyl, n-octyl, 2-ethylhexyl, 2, 2 And a 4-trimethylcyclohexyl group, decyl group, lauryl group, myristyl group, cetyl group or stearyl group. The compound of claim 14, wherein X ¹ , X ² and X ³ are hydrogen atoms; W is hydrogen atom or -CH ₂ -CH ₂ CO-OR; R is isopropyl group, n-butyl group, isobutyl group, amyl group, isoamyl group, n-hexyl group, cyclohexyl group, n-octyl group, 2-ethylhexyl group, 2, 2, 4-trimethyl The ultraviolet absorbent cosmetic composition which is a cyclohexyl group, a decyl group, a lauryl group, a myristyl group, a cetyl group, or a stearyl group. A compound according to claim 15, wherein B is a hydrogen atom or an acetyl group; X ¹ and X ³ are hydrogen atoms; X ² is a methoxyl group; Y is an oxygen atom or an imino group (-NH-); Z is a methyl group or a phenyl group; And wherein R is isopropyl, 2-ethylhexyl, lauryl, isostearyl, cyclohexyl or a 3, 3, 5-trimethylcyclohexyl group. The compound of claim 16, wherein X ¹ and X ² are methoxyl groups; X ³ is a hydrogen atom; W is hydrogen atom or -CH ₂ CH ₂ COOR; And R is a methyl, ethyl, n-butyl, isobutyl or 2-ethylhexyl group. 18. The compound of claim 17, wherein X ¹ , X ² and X ³ are hydrogen atoms; And wherein R is n-butyl, isobutyl, or 2-ethylhexyl group. Ultraviolet absorber containing an effective amount of the following general formula (I) compound:

Wherein A is a group represented by the following formula;

Wherein B is a hydrogen atom or an acetyl group; W is hydrogen atom or -CH ₂ -CH ₂ -CO-OR; Y is an oxygen atom or an imino group (-NH-); Z is a methyl group or a phenyl group; R is a straight chain alkyl group having 1 to 18 carbon atoms, or a branched chain or cyclic alkyl group having 3 to 18 carbon atoms; X ¹ , X ² and X ³ are independently a hydrogen atom, hydroxyl group or methoxyl group (two or three of which may be the same or both may be different); With A

R is not a hydrogen atom or an alkyl group having 1 to 2 carbon atoms, and A is

And when X ¹ , X ² and X ³ are hydrogen atoms, R is not an alkyl group having from 1 to 2 carbon atoms. The compound of claim 21, wherein A is

ego; B is a hydrogen atom or an acetyl group; Each X ¹ , X ² and X ³ is a hydrogen atom, hydroxyl group or methoxyl group; Y is an oxygen atom or an imino group (-NH-); Z is a methyl group or a phenyl group; And a UV absorber wherein R is a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms. The compound of claim 21, wherein A is

ego; X ¹ and X ³ are hydrogen atoms or methoxyl groups; X ² is a methoxyl group or a hydroxyl group; W is hydrogen atom or -CH ₂ -CH ₂ -COOR; And an ultraviolet absorber wherein R is a linear alkyl group having 1 to 18 carbon atoms or a branched or cyclic alkoxy group having 3 to 18 carbon atoms. The compound of claim 21, wherein A is

ego; X ¹ , X ² and X ³ are hydrogen atoms; W is hydrogen atom or -CH ₂ -CH ₂ -COOR; And a UV absorber wherein R is a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms. The compound of claim 22, wherein B is a hydrogen atom or an acetyl group; X ¹ and X ³ are hydrogen atoms or methoxyl groups; X ² is a methoxyl group or a hydroxyl group; Y is an oxygen atom or an imino group; R is isopropyl group, n-butyl group, isobutyl group, amyl group, isoamyl group, n-hexyl group, cyclohexyl group, n-octyl group, 2-ethylhexyl group, 2, 2, 4-trimethyl The ultraviolet absorber which is a cyclohexyl group, a decyl group, a lauryl group, a myristyl group, a cetyl group, or a stearyl group. The compound of claim 23, wherein X ¹ and X ² are methoxyl groups; X ³ is a hydrogen atom; W is hydrogen atom or -CH ₂ -CH ₂ -CO-OR; R is methyl, ethyl, isopropyl, n-butyl, isobutyl, amyl, isoamyl, n-hexyl, cyclohexyl, n-octyl, 2-ethylhexyl, 2, 2 And a 4-trimethylcyclohexyl group, decyl group, lauryl group, myristyl group, cetyl group or stearyl group. The compound of claim 24, wherein X ¹ , X ² and X ³ are hydrogen atoms; W is hydrogen atom or -CH ₂ -CH ₂ -CO-OR; R is isopropyl group, n-butyl group, isobutyl group, amyl group, isoamyl group, n-hexyl group, cyclohexyl group, n-octyl group, 2-ethylhexyl group, 2, 2, 4-trimethyl The ultraviolet absorber which is a cyclohexyl group, a decyl group, a lauryl group, a myristyl group, a cetyl group, or a stearyl group. A compound according to claim 25, wherein B is a hydrogen atom or an acetyl group; X ¹ and X ³ are hydrogen atoms; X ² is a methoxyl group; Y is an oxygen atom or an imino group (-NH-); Z is a methyl or phenyl group; And an ultraviolet absorber wherein R is isopropyl, 2-ethylhexyl, lauryl, isostearyl, cyclohexyl or a 3, 3, 5-trimethylcyclohexyl group. 27. The compound of claim 26, wherein X ¹ and X ² are methoxyl groups; X ³ is a hydrogen atom; W is hydrogen atom or -CH ₂ CH ₂ COOR; And R is a methyl, ethyl, n-butyl, isobutyl or 2-ethylhexyl group. The compound of claim 27, wherein X ¹ , X ² and X ³ are hydrogen atoms; W is a hydrogen atom; Moreover, the ultraviolet absorber whose R is n-butyl, isobutyl, or 2-ethylhexyl group.

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