JPH0812547A - Skin external preparation - Google Patents

Abstract

PURPOSE:To obtain a skin external preparation which comprises a combination of a specific amino acid derivative with a polyhydric alcohol, thus is high in safety, excellent in anti-active oxygen performance and gives smooth application feeling without greasy and creaky touch. CONSTITUTION:This skin external preparation comprises (A) at least one selected from amino acid derivatives of the formula [Ar is 2-hydroxyphenyl, 2-hydroxy-1-naphthyl, pyridyl; R<1> is an amino acid side chain; X is -CH2-NH-, -CH=N-; Y is H, -COOR<1> (R<1> is H, a 1-6C alkyl),-SO3H; n is 0, 1] or its salts, and (B) a polyhydric alcohol. The ingredient (A is preferably N-(2- hydroxybenzyl)-L-glutamic acid, and ingredient (B) is preferably propylene glycol or glycerol. The weight ratio of A/B is 0.01/99.99-90/10, particularly 0.05/99.95-50/50.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a skin external preparation containing an amino acid derivative having an excellent anti-oxygen activity and having a smooth feeling of use without giving a sticky feeling or a squeaky feeling to the skin and hair.

[0002]

2. Description of the Related Art In recent years, various disorders and diseases on the skin due to active oxygen species have been reported. For example, it is known that active oxygen species are deeply involved in the causes of skin aging, canceration, pigmentation, inflammation and the like due to sunlight, especially ultraviolet rays. Therefore, if the action of reactive oxygen species can be suppressed, it is expected that these skin disorders and diseases will be prevented.

[0003] Conventionally, as substances that suppress the action of reactive oxygen species, enzyme antioxidants such as superoxide dismutase (SOD), non-enzymatic antioxidants such as ascorbic acid, tocopherol and glutathione, or tannins Antioxidants derived from such plants are known. However, among these substances, SOD is expensive and chemically unstable, so its use is limited. As for non-enzymatic antioxidants such as ascorbic acid, tocopherol, and glutathione, there are many unstable compounds and the effect of suppressing active oxygen species is insufficient. Many plant-derived antioxidants such as tannins also have problems in stability such as being easily hydrolyzed and being easily oxidized themselves.

In recent years, some studies have been reported to suppress the generation of active oxygen species by capturing metal ions because metal ions present in the living body play the role of a catalyst in the generation of active oxygen species. (For example,
Free Radicals in Biology and Medicine.Oxford, Cla
rendon Press, p. 234, 1989). As a compound having a metal ion-trapping ability, a desferrioxamine-based compound is known, but this compound has a high metal-ion-trapping ability, which disturbs the balance of metal ions in a living body and is high. The price. Other than the desferrioxamine-based compounds, metal ion chelating agents such as 2,2'-dipyridyl, 1,10-phenanthrolene, and 2,2'-dipyridylamine have been studied, but most of them are skin irritants. Therefore, it is difficult to use it as an external preparation for skin.

[0005]

DISCLOSURE OF THE INVENTION The object of the present invention is to provide a highly safe and excellent anti-reactive oxygen ability, and to give a sticky feeling and a squeaky feeling to the skin and hair when applied to the skin or hair. It is an object of the present invention to provide an external preparation for skin having a smooth feeling of use.

[0006]

Means for Solving the Problems The inventors of the present invention have conducted intensive studies to achieve the above object, and as a result, the following general formula (I)
It was found that the above object can be achieved by using a polyhydric alcohol in combination with an amino acid derivative represented by or a salt thereof, and completed the present invention.

That is, the present invention relates to a skin external preparation characterized by containing the following components (A) and (B). (A) One or more kinds selected from the amino acid derivatives represented by the following general formula (I) or salts thereof (B) Polyhydric alcohol

[0008]

Embedded image (In the formula, Ar represents a 2-hydroxyphenyl group, a 2-hydroxy-1-naphthyl group or a pyridyl group, and one or more hydrogen atoms bonded to an aromatic ring of these groups are independently a halogen atom. May be substituted with an alkyl group having 1 to 6 carbon atoms, a hydroxyl group, a hydroxyalkyl group having 1 to 6 carbon atoms, a nitro group, an alkoxyl group having 1 to 6 carbon atoms, or a carboxyl group,
R represents a side chain of an amino acid, X represents N- and -CH ₂ -NH- or -CH =, Y is a hydrogen atom, -COOR ^{1,
_{-SO 3 H, -CON (R 2}} ) R 3, -CONHCH
(R ⁵ ) represents COOR ⁴ or —CH ₂ OH (in the group,
R ^{1 to} R ⁴ represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R ⁵ represents a side chain of an amino acid. ) And n represents an integer of 0 or 1. )

The present invention will be described in detail below. (A) In the amino acid derivative represented by the above general formula (I) used in the present invention, R is, for example, an acidic amino acid such as glutamic acid, aspartic acid, cysteic acid or homocystine acid, glycine, alanine, valine or leucine. ,
Examples include neutral amino acids such as isoleucine, phenylalanine, tryptophan, threonine, serine, homoserine, tyrosine, cysteine, methionine, glutamine, and arginine; and side chains of basic amino acids such as lysine, ornithine, arginine, and histidine. When these have an asymmetric carbon atom, they may be either optically active or racemic. Examples of the salt include alkali metal salts such as sodium and potassium, alkaline earth metal salts such as magnesium and calcium, and inorganic amine salts such as ammonia.
Organic amine salts such as monoethanolamine, diethanolamine, triethanolamine, 2-amino-2-methyl-1-propanol, 2-amino-2-methyl-1,3-propanediol, lysine, ornithine, and arginine. be able to. You may use these salts in combination of 2 or more types. These may be blended as an amino acid derivative salt, or the amino acid derivative and the base may be separately blended to form an amino acid derivative salt in the composition.

A preferred specific example of the amino acid derivative used in the present invention is N- (2-hydroxybenzyl).
-L-glutamic acid, N- (2-hydroxybenzyl)
-L-aspartic acid, N- (2-hydroxybenzyl) glycine, N- (2-hydroxybenzyl) -L-
Alanine, N- (2-hydroxybenzyl) -DL-alanine, N- (2-hydroxybenzyl) -L-threonine, N- (2-hydroxybenzyl) -L-tyrosine, N- (2-hydroxybenzyl)- L-phenylalanine, N- (2-hydroxybenzyl) -L-serine, N- (2-hydroxybenzyl) -L-histidine, N- (2-hydroxybenzyl) -L-arginine and the like can be mentioned.

The amino acid derivative represented by the above general formula (I) is, for example, a 2-hydroxy aromatic aldehyde such as salicylaldehyde and an amino alcohol or an ester, amide or amino alcohol obtained by reducing an amino acid in a solvent. Or by reacting without solvent,
Further, it can be easily derived by adding a hydrogenating agent such as sodium borohydride, if necessary.

Preferred specific examples of the polyhydric alcohol (B) used in the present invention include polyoxyethylene glycol (3 to 12 EO adduct), propylene glycol, 1,3-butylene glycol, glycerin, sorbitol, Examples thereof include polyglycerin, maltitol, dipropylene glycol, polyethylene glycol and the like.

Any one of the above components (A) and (B) may be used alone, or two or more of them may be used in combination.

The blending ratio of the component (A) and the component (B) in the external preparation for skin of the present invention is usually 0.01 / by weight.
99.99 to 90/10, preferably 0.05 / 99.
95-50 / 50. When the content ratio of the polyhydric alcohol is less than 10, there is a problem in use feeling such as squeaky feeling on the skin or hair, which is not preferable. Also, 9
If it exceeds 9.99, the skin feels sticky,
There is a problem in the feeling of use, which is not preferable.

The total content of the component (A) and the component (B) in the external preparation for skin of the present invention is 0.01 to 80% by weight, preferably 0.02 to 50% by weight. 0.01
If it is less than 80% by weight, the anti-oxygen activity is not sufficiently exerted,
When the content is more than 10% by weight, there is a problem in use feeling such as stickiness, which is not preferable.

In addition to the components (A) and (B), the components for general external use for the skin can be added to the external preparation for the skin of the present invention within a range that does not impair the effects of the present invention. . Components commonly used in skin external preparations include urea, ethanol, isopropanol, anionic surfactant, amphoteric surfactant, nonionic surfactant, cationic surfactant, oil and fat, polymer compound, emulsifier, powder, Antibiotics and the like can be mentioned.

Examples of the anionic surfactant include lauric acid, myristic acid, palmitic acid, stearic acid,
Higher fatty acid salts such as coconut oil fatty acids, hardened tallow fatty acids, and oleic acid, N-long-chain acylglutamic acid, N-long-chain acylaspartic acid, N-long-chain acylglycine, N-long-chain acylalanine, N-long-chain acylsarcosine , N-long chain acyl-β-alanine, N-long chain acyl-N-methyl-β
N-acyl carboxylate salts such as alanine, sodium polyoxyethylene (3EO) lauryl ether acetate,
Polyoxyethylene (3EO) lauryl ether acetic acid, polyoxyethylene (3EO) tridecyl ether acetate sodium, polyoxyethylene (3EO) tridecyl ether acetic acid, polyoxyethylene (4.5E.
O.) sodium lauryl ether acetate, sodium polyoxyethylene (6EO) tridecyl ether acetate, polyoxyethylene (7EO) tridecyl ether acetic acid, polyoxyethylene (3EO) sodium stearyl ether acetate , Polyoxyethylene (3E.
O.) Sodium octyl ether acetate, ether carboxylate such as polyoxyethylene (3EO) lauryl ether acetate monoethanolamine, etc., triethanolamine dodecylbenzenesulfonate, sodium dodecylbenzenesulfonate, sodium α-olefin sulfonate (C12) alkylsulfonates, dioctyl sodium sulfosuccinate, disodium lauryl sulfosuccinate, disodium tallowamide sulfosuccinate, polyoxyethylene (1-5EO) disodium lauryl sulfosuccinate, polyoxyethylene (3E.
O.) disodium myristyl sulfosuccinate, polyoxyethylene sulfosuccinate (5EO) lauroylethanolamide disodium, sulfosuccinates such as polyoxyethylene sulfosuccinate (2EO) monosodium amide disodium, cocoyl- N-acyl sulfonates such as sodium N-methyltaurate, sodium lauroyl-N-methyltaurine, cocoyl-N-methyltaurine triethanolamine, lauroyl-N-methyltaurine triethanolamine, sodium cocoylisethionate, lauroylise Sodium thionate,
O-acyl sulfonates such as cocoyl isethionate triethanolamine, lauroyl isethionate triethanolamine, etc., sodium lauryl sulfate, sodium myristyl sulfate, sodium palmityl sulfate, lauryl sulfate triethanolamine, myristyl sulfate triethanolamine, palmityl sulfate Alkyl sulfates such as triethanolamine, polyoxyethylene (2-4EO) lauryl ether sodium sulfate, polyoxyethylene (2
~ 4EO) lauryl ether triethanolamine sulfate, polyoxyethylene (2-4EO) myristyl ether sodium sulfate, polyoxyethylene (2-4
EO) myristyl ether sulfate triethanolamine, polyoxyethylene (2-4 EO) sodium palmityl ether sulfate, polyoxyethylene (2-4)
EO) ether sulfates such as palmityl ether triethanolamine sulfate, sodium lauryl phosphate, triethanolamine lauryl phosphate, sodium myristyl phosphate, triethanolamine myristyl phosphate, sodium oleyl phosphate, triethanol oleyl phosphate Amine, polyoxyethylene (2-4EO) lauryl ether sodium phosphate, polyoxyethylene (2
~ 4EO) lauryl ether triethanolamine phosphate, polyoxyethylene (2-4EO) myristyl ether sodium phosphate, polyoxyethylene (2 ~ 4EO)
4EO) myristyl ether triethanolamine phosphate, polyoxyethylene (2-4EO) sodium oleyl ether phosphate, polyoxyethylene (2-4)
EO) alkyl phosphates such as oleyl ether triethanolamine phosphate.

Examples of the amphoteric surfactant include betaine lauryl dimethylamino acetate, betaine myristyl dimethyl amino acetate, betaine palmityl dimethyl amino acetate, betaine stearyl dimethyl amino acetate, betaine coconut oil alkyl dimethyl amino acetate, betaine lauryl dihydroxyethyl acetate, Myristyl dihydroxyethyl acetate betaine, palmityl dihydroxyethyl acetate betaine, stearyl dihydroxyethyl acetate betaine,
Alkyl betaines such as coconut oil alkyldihydroxyethyl acetate betaine, lauric acid amidopropyl betaine, myristic acid amidopropyl betaine, palmitic acid amidopropyl betaine, stearic acid amidopropyl betaine, and coconut oil fatty acid amidopropyl betaine, lauryl dimethylamino-2-hydroxy Propyl sulfobetaine, myristyl dimethylamino-2-hydroxypropyl sulfobetaine, palmityl dimethylamino-2
-Hydroxypropylsulfobetaine, stearyldimethylamino-2-hydroxypropylsulfobetaine,
Palm oil alkyl dimethylamino-2-hydroxypropyl sulfobetaine, lauryl dimethylaminopropyl sulfobetaine, myristyl dimethylaminopropyl sulfobetaine, palmityl dimethylaminopropyl sulfobetaine, stearyl dimethylaminopropyl sulfobetaine, coconut oil alkyl dimethylaminopropyl sulfobetaine Sulfobetaine, 2-lauryl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, 2-myristyl-N-carboxymethyl-N
-Hydroxyethyl imidazolinium betaine, 2-palmityl-N-carboxymethyl-N-hydroxyethyl imidazolinium betaine, 2-stearyl-N-carboxymethyl-N-hydroxyethyl imidazolinium betaine, alkyl 2-coconut oil- An imidazolinium derivative such as N-carboxymethyl-N-hydroxyethyl imidazolinium betaine can be used.

As nonionic surfactants, lauric acid monoethanolamide, myristic acid monoethanolamide, palmitic acid monoethanolamide, stearic acid monoethanolamide, coconut oil fatty acid monoethanolamide, lauric acid diethanolamide, myristic acid diethanolamide. , Palmitic acid diethanolamide, stearic acid diethanolamide, coconut oil fatty acid diethanolamide, polyoxyethylene (2EO) lauric acid monoethanolamide, polyoxyethylene (2EO) myristic acid monoethanolamide, polyoxyethylene (2EO) palmitic acid monoethanolamide, polyoxyethylene (2EO) stearic acid monoethanolamide, polyoxyethylene (2E.O.)
O.) Fatty acid alkanolamides such as coconut oil fatty acid monoethanolamide, and sugar-based compounds such as alkylglycoside derivatives and sugar alcohol hydroxyaliphatic ether derivatives can be mentioned.

As the cationic surfactant, Nα-cocoyl-L-arginine ethyl ester / DL-pyrrolidone carboxylate, Nα-cocoyl-L-arginine ethyl ester / hydrochloride, Nα-cocoyl-L-arginine ethyl ester / Lactate, Nα-cocoyl-L-arginine ethyl ester succinate, Nα-cocoyl-L
-Arginine ethyl ester / citrate, Nα-cocoyl-L-arginine ethyl ester / malate, N
α-cocoyl-L-arginine ethyl ester / phosphate, Nα-cocoyl-L-arginine ethyl ester / phosphate
Glutamate, Nα-cocoyl-L-arginine ethyl ester / aspartate, Nα-cocoyl-L-
Arginine ethyl ester / sulfate, Nα-cocoyl-
L-arginine methyl ester / DL-pyrrolidone carboxylate, Nα-lauroyl-L-arginine ethyl ester / DL-pyrrolidone carboxylate, Nα-myristoyl-L-arginine ethyl ester / DL-pyrrolidone carboxylate, Nα-palmitoyl -L-arginine ethyl ester / DL-pyrrolidone carboxylate, N
α-stearoyl-L-arginine ethyl ester D
L-pyrrolidone carboxylate, Nα-oleoyl-L-
Nα-long chain acyl arginine lower alkyl ester salts such as arginine ethyl ester / DL-pyrrolidone carboxylate, Nε-lauroyl-L-lysine ethyl ester / DL-pyrrolidone carboxylate, Nε-lauroyl-
L-lysine ethyl ester / hydrochloride, Nε-lauroyl-L-lysine ethyl ester / lactate, Nε-lauroyl-L-lysine ethyl ester / succinate, Nε-lauroyl-L-lysine ethyl ester / citrate, N
ε-lauroyl-L-lysine ethyl ester / malate, Nε-lauroyl-L-lysine ethyl ester / phosphate, Nε-lauroyl-L-lysine ethyl ester / glutamate, Nε-lauroyl-L-lysine ethyl ester・ Aspartate, Nε-lauroyl-L
-Lysine ethyl ester / sulfate, Nε-lauroyl-
L-lysine methyl ester / hydrochloride, Nε-cocoyl-
L-lysine ethyl ester / hydrochloride, Nε-myristoyl-L-lysine ethyl ester / hydrochloride, Nε-palmitoyl-L-lysine ethyl ester / hydrochloride, Nε-stearoyl-L-lysine ethyl ester / hydrochloride, Nε
-Oleoyl-L-lysine ethyl ester, N 酸 塩 -alkyl lysine lower alkyl ester salt such as hydrochloride, lauryltrimethylammonium chloride, myristyltrimethylammonium chloride, palmityltrimethylammonium chloride, stearyltrimethylammonium chloride, oleyltrimethylammonium chloride, eico Monoalkyl quaternary ammonium salts such as siltrimethylammonium chloride, lauryldimethylbenzylammonium chloride, stearyldimethylbenzylammonium chloride, behenyltrimethylammonium chloride, dipalmityldimethylammonium chloride, distearyldimethylammonium chloride, dihydrogenated tallow alkyldimethyl Ammonium bromer Dialkyl quaternary ammonium salts such as dihydrogenated beef tallow alkyldimethylammonium methylsulfate, distearyl polyethenoxymethylammonium chloride, dipalmitylpolyethenoxyethylammonium chloride, dipalmitylpolyethenoxyhydroxyethylammonium chloride, Tristearyl polyethenoxy ammonium bromide,
Examples thereof include alkylpolyethenoxy quaternary ammonium salts such as distearyl polyethenoxyethylammonium ethyl sulfate.

The fats and oils include avocado oil, almond oil, olive oil, cocoa butter, beef tallow, sesame oil, wheat germ oil, safflower oil, shea butter, turtle oil, camellia oil, persic oil, castor oil, grape oil, macadamia nut oil. Triglycerides such as mink oil, egg yolk oil, owl, coconut oil, rosehip oil, soybean oil, cottonseed oil, hydrogenated oil, orange luffy oil, carnauba wax, candelilla wax, whale wax, jojoba oil, monta wax, beeswax, lanolin, etc. Hydrocarbons such as wax, liquid paraffin, petrolatum, paraffin, ceresin, microcrystalline wax, squalane, lauryl alcohol, cetyl alcohol, cetostearyl alcohol, stearyl alcohol, oleyl alcohol, behenyl alcohol, lanolin alcohol, hydrogenated alcohol Phosphorus alcohol, hexyldecanol, octyldodecanol, isostearyl alcohol, jojoba alcohol, higher alcohols such as decyltetradecanol, cholesterol, dihydrocholesterol, sterols such as phytosterol, oleyl oleate, ethyl linoleate, isopropyl myristate, lanolin fatty acid isopropyl Hexyl laurate, myristyl myristate, cetyl myristate, octyldodecyl myristate, decyl oleate, octyldodecyl oleate, hexyldecyl dimethyloctanoate, cetyl isooctanoate, cetyl palmitate,
Glycerin trimyristate, glyceryl tri (caprylate / caprate), propylene glycol dioleate, glycerin triisostearate, glyceryl triisooctanoate, cetyl lactate, myristyl lactate, diisostearyl malate, cholesteryl stearate, cholesteryl isostearate, 12 And fatty acid esters such as cholesteryl hydroxystearate, glyceryl pyroglutamate oleate, di (cholesterol, behenyl, octyldodecyl alcohol) -N-lauroyl-L-glutamate, and the like.

As the polymer compound, gum arabic, tragacanth gum, guar gum, locust bean gum, karaya gum, iris moss, quince seed, gelatin,
Shellac, rosin, casein, sodium carboxymethylcellulose, hydroxyethylcellulose, methylcellulose, ethylcellulose, sodium alginate, ester gum, nitrocellulose, hydroxypropylcellulose, crystalline cellulose, polyvinyl alcohol, polyvinylpyrrolidone, sodium polyacrylate, carboxyvinyl polymer, polyvinylmethyl Examples include ether, polyamide resin, silicone oil, chitin, partially deacetylated chitin, hydrolyzed collagen, polyaspartic acid, sodium polyglutamate, xanthan gum and the like.

As the emulsifier, glyceryl monostearate, diglycerin monostearate, polyglycerin monostearate, sorbitan monostearate, sorbitan monooleate, sorbitan monosesquioleate, sorbitan monolaurate, polyethylene glycol monostearate, Polyethylene glycol monooleate, polyethylene glycol monolaurate, polyethylene glycol distearate, polyethylene glycol dioleate, polyethylene glycol dilaurate, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene cetyl ether, polyoxyethylene lauryl ether,
Polyoxyethylene nonyl phenyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene sorbit beeswax, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan monooleate, polyoxyethylene sorbitan monolaurate, ethylene glycol monostearate, etc. Can be mentioned.

As powders, talc, kaolin, titanium dioxide, titanium-coated mica, mica, iron oxide, silicic acid, ultramarine blue,
Examples include inorganic powders such as dark blue, zinc white, clay, precipitated calcium carbonate, bismuth oxychloride, pentonite, and montmorillonite, and organic powders such as Nε-lauroyl lysine, guanine, and laminating resin pearlescent agent.

Examples of the antibiotics include erythromycin, streptomycin, teramycin, aurethricin, gramicidin, chloramphenicol, aureomycin, dihydrostreptomycin, baicillin, bacitracin, neomycin, penicillin, polymyxin B, leucomycin and the like. it can.

The dosage form of the external preparation for skin of the present invention is not particularly limited and may be any dosage form such as solution, paste, gel, solid, and powder. Further, the external preparation for skin of the present invention is an oil, lotion, cream, emulsion, gel, shampoo, hair rinse, hair conditioner, enamel, foundation, lipstick, white powder,
Packs, ointments, perfumes, powders, colognes, soaps,
In addition to cosmetics or cleaning agents such as aerosols and cleansing foams, skin aging preventive improvers, skin inflammation preventive improvers, bath agents, hair nourishes, skin serums, sunscreens, or prevention of rough skin due to trauma, irritations, cracks, etc. It can be used as an improver and the like.

Further, other commonly used ingredients in the external preparation for skin can be added to the external preparation for skin of the present invention within a range not impairing the effects of the present invention. Other commonly used ingredients in the external preparation for skin include sodium DL-pyrrolidone carboxylate, sodium lactate, moisturizers such as Produ 100 (Ajinomoto Co.), Produ 200 (Ajinomoto Co.), ethylenediaminetetraacetic acid, citric acid, and ascorbic acid.
Maleic acid, succinic acid, kephalin, saccharinic acid, hexametaphosphoric acid, 1-hydroxyethane-1,1-diphosphonic acid, dihydroxyethylglycine, or chelating agents such as salts thereof, crude drugs, vitamins, hormones, antihistamines, skin Drugs such as astringents, cantharis tincture, capsicum tincture, ginseng tincture, assembly extract, garlic extract, hinokitiol, carpronium chloride, pentadecanoic acid glyceride, estrogen, hair growth promoters such as various photosensitizers, arbutin and other various hydroquinones Whitening agents such as glycosides, dibutylhydroxytoluene, butylhydroxyanisole,
Antioxidants such as propyl gallate, tocopherol, placenta extract, elastin, collagen, aloe extract, hamamelis water, loofah water, chamomile extract, licorice extract and other animal and plant extract components, cresol derivatives, paraben derivatives, etc. Antifungal agents, hormones such as corticosteroids, amino acids, softeners, emollients, texture improvers, superfatting agents, viscosity modifiers, pearlizing agents, anti-inflammatory agents, ultraviolet absorbers, pH modifiers, fragrances, pigments Etc. can be mentioned.

[0028]

EXAMPLES The present invention will now be described in more detail with reference to examples, but the present invention is not limited to these examples. In addition, in this example, the blending amount was represented by wt%.

Synthesis Example 1 9 g of glycine was dissolved in 60 ml of a 2N aqueous sodium hydroxide solution, and then 12 ml of salicylaldehyde and 1.3 g of sodium borohydride were sequentially added thereto. After stirring for 1 hour, 12 ml of salicylaldehyde and 1.3 g of sodium borohydride were sequentially added again. After stirring at room temperature for 1 hour, the insoluble matter was filtered off, and the filtrate was extracted with diethyl ether. The pH was adjusted to 4 with hydrochloric acid to obtain 17 g of N- (2-hydroxybenzyl) glycine. Similarly,
Various N- (2-hydroxybenzyl) amino acids or N- (4-pyridoxyl) methylene amino acids were obtained.

Synthesis Example 2 1.6 g of L-histidine and 2.6 g of 2-hydroxy-1-naphthaldehyde were added to 220 ml of ethanol,
By stirring for 5 days, N- (2-hydroxy-1-
2.4 g of naphthal) -L-histidine was obtained. Similarly, various N- (2-hydroxy-1-naphthal)
Amino acid or N- (4-pyridoxylidene) amino acid was obtained.

Test Example As a skin external preparation, the feeling of use was evaluated by the sensory evaluation of 10 panelists of male and female. Table 1 shows the evaluation criteria of each evaluation item. For sensory evaluation, the formulations shown in Table 2 were prepared.

[0032]

[Table 1]

[0033]

[Table 2]

As shown in Table 2, none of the products had a sticky feeling or a squeaky feeling, and the usability was sufficiently satisfactory.

Examples 7 to 8 Body shampoo Body shampoos having the compositions shown in Tables 3 and 4 were prepared by a conventional method. This product showed neither sticky feeling nor squeaky feeling, and the usability was sufficiently satisfactory.

[0036]

[Table 3]

[0037]

[Table 4]

Example 9 Face Wash Foam A face wash foam having the composition shown in Table 5 was prepared by a conventional method.
This product showed neither sticky feeling nor squeaky feeling, and the usability was sufficiently satisfactory.

[0039]

[Table 5]

Examples 10 to 12 Lotions Lotions having the compositions shown in Tables 6 to 8 were prepared by a conventional method. This product showed neither sticky feeling nor squeaky feeling, and the usability was sufficiently satisfactory.

[0041]

[Table 6]

[0042]

[Table 7]

[0043]

[Table 8]

Example 13 Lotion A lotion having the composition shown in Table 9 was prepared by a conventional method. This product showed neither sticky feeling nor squeaky feeling, and the usability was sufficiently satisfactory.

[0045]

[Table 9]

Examples 14 to 16 Cosmetic creams Cosmetic creams having the compositions shown in Tables 10 to 12 were prepared by a conventional method. This product showed neither sticky feeling nor squeaky feeling, and the usability was sufficiently satisfactory.

[0047]

[Table 10]

[0048]

[Table 11]

[0049]

[Table 12]

Example 17 Cleansing Foam A cleansing foam having the composition shown in Table 13 was prepared by a conventional method. This product showed neither sticky feeling nor squeaky feeling, and the usability was sufficiently satisfactory.

[0051]

[Table 13]

Example 18 Emulsion An emulsion having the composition shown in Table 14 was prepared by a conventional method. This product showed neither sticky feeling nor squeaky feeling, and the usability was sufficiently satisfactory.

[0053]

[Table 14]

Example 19 Pack A pack having the composition shown in Table 15 was prepared by a conventional method. This product showed neither sticky feeling nor squeaky feeling, and the usability was sufficiently satisfactory.

[0055]

[Table 15]

Example 20 Lipstick A lipstick having the composition shown in Table 16 was prepared by a conventional method. This product showed neither sticky feeling nor squeaky feeling, and the usability was sufficiently satisfactory.

[0057]

[Table 16]

Examples 21 to 24 Hair Shampoos Hair shampoos having the compositions shown in Tables 17 to 20 were prepared by a conventional method. This product showed neither sticky feeling nor squeaky feeling, and the usability was sufficiently satisfactory.

[0059]

[Table 17]

[0060]

[Table 18]

[0061]

[Table 19]

[0062]

[Table 20]

Example 25 Rinse A rinse having the composition shown in Table 21 was prepared by a conventional method. This product showed neither sticky feeling nor squeaky feeling, and the usability was sufficiently satisfactory.

[0064]

[Table 21]

Example 26 Hair conditioner A hair conditioner having the composition shown in Table 22 was prepared by a conventional method. This product showed neither sticky feeling nor squeaky feeling, and the usability was sufficiently satisfactory.

[0066]

[Table 22]

Example 27 Permanent Wave Agent A permanent wave agent having the composition shown in Table 23 was prepared by a conventional method. This product showed neither sticky feeling nor squeaky feeling, and the usability was sufficiently satisfactory.

[0068]

[Table 23]

Example 28 Hair Growth Promoter A hair growth promoter having the composition shown in Table 24 was prepared by a conventional method.
This product showed neither sticky feeling nor squeaky feeling, and the usability was sufficiently satisfactory.

[0070]

[Table 24]

Example 29 Hair dye A hair dye having the composition shown in Table 25 was prepared by a conventional method. This product showed neither sticky feeling nor squeaky feeling, and the usability was sufficiently satisfactory.

[0072]

[Table 25]

Example 30 Toothpaste A toothpaste having the composition shown in Table 26 was prepared by a conventional method. This product showed neither sticky feeling nor squeaky feeling, and the usability was sufficiently satisfactory.

[0074]

[Table 26]

Example 31 Sun Protection Cream A sun protection cream having the composition shown in Table 27 was prepared by a conventional method. This product does not show stickiness or squeaky feeling,
The feeling of use was sufficiently satisfactory.

[0076]

[Table 27]

Example 32 Acne lotion Acne lotion having the composition shown in Table 28 was prepared by a conventional method. This product showed neither sticky feeling nor squeaky feeling, and the usability was sufficiently satisfactory.

[0078]

[Table 28]

Example 33 Whitening agent A whitening agent having the composition shown in Table 29 was prepared by a conventional method. This product showed neither sticky feeling nor squeaky feeling, and the usability was sufficiently satisfactory.

[0080]

[Table 29]

Examples 34 to 40 Ointments Ointments having the compositions shown in Tables 30 to 36 were prepared by a conventional method. This product showed neither sticky feeling nor squeaky feeling, and the usability was sufficiently satisfactory.

[0082]

[Table 30]

[0083]

[Table 31]

[0084]

[Table 32]

[0085]

[Table 33]

[0086]

[Table 34]

[0087]

[Table 35]

[0088]

[Table 36]

[0089]

The external preparation for skin of the present invention has high safety,
It has an excellent anti-oxygen activity and, when applied to the skin or hair, does not give a sticky feeling or a squeaky feeling to the skin and the hair, and has a smooth usability.

Claims (1)

[Claims] 1. An external preparation for skin comprising the following component (A) and component (B). (A) one or more selected from amino acid derivatives represented by the following general formula (I) or salts thereof (B) polyhydric alcohol (In the formula, Ar represents a 2-hydroxyphenyl group, a 2-hydroxy-1-naphthyl group or a pyridyl group, and one or more hydrogen atoms bonded to an aromatic ring of these groups are independently a halogen atom. May be substituted with an alkyl group having 1 to 6 carbon atoms, a hydroxyl group, a hydroxyalkyl group having 1 to 6 carbon atoms, a nitro group, an alkoxyl group having 1 to 6 carbon atoms, or a carboxyl group,
R represents a side chain of an amino acid, X represents N- and -CH ₂ -NH- or -CH =, Y is a hydrogen atom, -COOR ^{1,
_{-SO 3 H, -CON (R 2}} ) R 3, -CONHCH
(R ⁵ ) represents COOR ⁴ or —CH ₂ OH (in the group,
R ^{1 to} R ⁴ represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R ⁵ represents a side chain of an amino acid. ) And n represents an integer of 0 or 1. )