JP2000119154A - Skin lotion - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject lotion having a high emollient effect and an excellent drabness preventing effect on skin by adding a specific α-amino acid derivative and carboxylic acid ester to a specified cholesterol ester inclusion substance. SOLUTION: This lotion includes (A) a cholesterol ester inclusion substance obtained by including a cholesterol ester (e.g. an ester of cholesterol and a higher fatty acid such as myristic acid, etc.), in a hydroxyalkylated cyclodextrin (hereinafter HACD; e.g. hydroxyethylated cyclodextrin, etc.), (e.g. the amount ratio of HACD to the cholesterol ester is preferably 99:1 to 90:10) and (B) an α-amino acid derivative of the formula (R1 is H or a 1-6C alkyl; R2 and R3 are each H, a 1-6C alkyl or an acyl), its salt, carboxylic acid ester and its quaternary ammonium in the ratio of 0.01-20.0 wt.% of the component A and 0.001-10.0 wt.% of the component B.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an external preparation for skin. In particular, it has a high emollient effect on the skin,
The present invention relates to an external preparation for skin having an effect of preventing dullness.

[0002]

2. Description of the Related Art Conventionally, dullness of the skin has occupied the top place in women's skin troubles, and although it is a major cosmetic problem, the phenomenon itself has many vague aspects. Dullness of the skin is a specific visual phenomenon that occurs throughout the face or in areas around the eyes or cheeks, which reduces redness and increases yellowness of the skin and / or reduces glossiness of the skin The boundary is unclear in a state in which the brightness is reduced and the image looks dark due to the drip or the shadow due to the unevenness or the like on the skin surface.

[0003] The following are assumed as causes of dullness of the skin, and these factors are grasped as specific phenomena by involving one or more of them. Deterioration of redness of skin color due to poor blood circulation Deterioration of plaque formation with indistinct borders or pigmentation of fine spots Influence of fine irregularities on skin surface caused by reduced elasticity of skin, etc. Hyperplasia or exfoliation of stratum corneum Decrease in transparency (light transmission) due to irregularity Reduced gloss due to irregular reflection on skin surface Yellowing of skin Changes in skin color due to estrous cycle Dullness due to dirt such as dust, sweat, and sebum

[0004] In recent years, attempts to improve the dullness of the skin have been made from various viewpoints.
"Desmosome degradation promoter" disclosed in JP-A-547.

[0005]

However, although these skin external preparations for preventing dulling have an excellent dulling-preventing effect, the anti-dulling agent has little effect on preventing the evaporation of moisture on the skin. However, it was not possible to expect a reduction in gloss due to the elasticity of the skin indicated by the symbol or irregular reflection on the skin surface indicated by the symbol.

In order to solve the above problems, it is necessary to develop a skin external preparation having a so-called emollient effect in addition to a moisturizing effect. Here, the emollient effect is
This is a skin roughness improving effect when skin roughness occurs. Then, an object of the present invention is to provide a skin external preparation which has an emollient effect and is excellent in a dullness preventing effect.

[0007]

Means for Solving the Problems The present inventor has conducted intensive studies to solve the above-mentioned problems. As a result, a skin external preparation prepared by combining, as active ingredients, a clathrate in which a cholesterol ester is included in a hydroxyalkylated cyclodextrin and a specific α-amino acid derivative or a salt thereof has a high emollient effect on the skin. There is, and found that it is more excellent in the effect of preventing dullness,
The present invention has been completed.

[0008] That is, the present invention provides an external preparation for skin characterized by containing the following (A) and (B) as active ingredients. (A) Cholesterol ester clathrate containing cholesterol ester with hydroxyalkylated cyclodextrin (B) Formula (I)

Embedded image (Where R¹Is a hydrogen atom or a straight chain having 1 to 6 carbon atoms or
Is a branched group (hereinafter referred to as a “C 1-6 straight-chain or branched” group)
Simply referred to as a "lower" group. ) Unsubstituted or substituted alkyl
R represents a group^TwoAnd R^ThreeAre independently hydrogen atoms, low
Represents a lower alkyl group or an acyl group. Α)
-Amino acid derivatives, salts or carboxylic esters thereof,
And its quaternary ammonium (provided that R^TwoAnd R^ThreeBut
Only when it is a lower alkyl group. Compound selected from)
More than one kind of thing

In the present invention, R ¹ is a substituted alkyl group, and the substituent is a hydroxyl group, a mercapto group (which may be substituted with a lower alkyl group), an amino group (however, a lower alkyl group). Group, lower acyl group, amidino group,
It may be substituted with an N-mono- or N, N'-di-lower alkylated amidino group or a hydroxyl group. ), A phenyl group (but may be substituted with a hydroxyl group),
A skin external preparation as described above, which is a 5-membered heterocyclic group having one or two nitrogen atoms in the ring (however, a benzene ring may be condensed) or a carbamoyl group. I do.

The present invention also relates to the above R ¹ , R ² and R ³
Wherein ^one of R ² and R ³ and R ¹ together form a propane-1,3-diyl group or a 2-hydroxypropane-1,3-diyl group And a skin external preparation.

In the present invention, the amount of the component (A) is 0.01 to 20.0% by weight, and the amount of the component (B) is 0.001 to 10.0% by weight. The above-mentioned external preparation for skin is provided.

The present invention also relates to the present invention, wherein the inclusion ratio of hydroxyalkylated cyclodextrin to cholesterol ester in the cholesterol ester clathrate is 99: 1 to 90: 1.
0. The above-mentioned external preparation for skin characterized by being 0.

Further, the present invention provides the above external preparation for skin, wherein the emulsion type is an oil-in-water type.

[0014]

Embodiments of the present invention will be described below.

Component (A) The cholesterol ester clathrate blended in the present invention comprises:
Hydroxyalkylated cyclodextrin (hereinafter referred to as “H
ACD ". ) In which a cholesterol ester is included.

The HACD used in the cholesterol ester clathrate of the present invention is obtained by introducing a hydroxyalkyl group into a hydroxyl group of cyclodextrin (hereinafter referred to as “CD”) which is well known as a cyclic oligosaccharide. It is something which raised.

CD is an oligosaccharide in which glucose residues are cyclically linked by α-1,4-linkage, α-CD consisting of 6 glucose residues, β-CD consisting of 7 glucose residues, 8
Γ-CDs consisting of individual γ-CDs are generally known. In the present invention, one or more of these CDs can be selected and used. Further, it can be used in the form of a starch hydrolyzate containing α, β, and γ CDs at the same time.

As the hydroxyalkyl group to be substituted for the hydroxyl group of CD, a hydroxyethyl group, a hydroxypropyl group and the like are mainly used. HACD can be obtained by performing a substitution reaction of these with a hydroxyl group. HA
Examples of the CD include hydroxyethylated CD, hydroxypropylated CD, hydroxybutylated CD, dihydroxypropylated CD, and the like. In the present invention, the substitution degree of the hydroxyl group and the hydroxyalkyl group is preferably 1 to 14 per CD.

Among these hydroxyalkylated cyclodextrins, considering the price, ease of production, usability, and water solubility, hydroxyethylated β-CD or hydroxypropylated β-CD or hydroxypropyl Β-CD is preferred, but not limited thereto.

As a method for producing the HACD, several methods have been conventionally known, and an example is shown below. That is, 100 g of β-CD was added to a 20% NaOH aqueous solution 15
0 ml of propylene oxide 5 while maintaining at 30 ° C.
0 ml is gradually added dropwise, and the mixture is stirred for 20 hours to continue the reaction.
After completion of the reaction, the mixture is neutralized to pH 6.0 with hydrochloric acid, placed in a dialysis membrane tube, and desalted under running water for 24 hours. Thereafter, drying is performed with a freeze dryer, and hydroxypropylated β-CD
About 90 g are obtained. This hydroxypropylated β-C
The degree of substitution of D per CD was 5.1.

As the cholesterol ester used in the cholesterol ester clathrate of the present invention, an ester of cholesterol and a higher fatty acid is used. Examples of the higher fatty acids that can be used in the present invention include myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, and arachidonic acid. In the present invention, one or more of these higher fatty acids are selected and used.

The amount ratio of HACD to cholesterol ester in the cholesterol ester clathrate of the present invention is 9
It is preferably from 9: 1 to 90:10. When the amount of the cholesterol ester exceeds 90:10, the cholesterol ester becomes excessive and stickiness occurs.
On the other hand, if the amount of the cholesterol ester is less than 99: 1, the amount of the cholesterol ester clathrate formed is small, and it is difficult to ensure water retention at the time of application.

The content of the cholesterol ester clathrate used in the present invention is 0.0% of the total amount of the external preparation for skin.
1 to 20.0% by weight, more preferably 0.1 to 5% by weight.
% By weight. If the amount is less than 0.01% by weight, the effect of suppressing water evaporation is insufficient. On the other hand, if the amount exceeds 20.0% by weight, no further effect can be obtained.

Component (B) In the present invention, the following formula (I)

Embedded image An α-amino acid derivative represented by the formula:
Acid ester and its quaternary ammonium
One or more compounds are used.

R ¹ represents a hydrogen atom or an unsubstituted or substituted lower alkyl group. Here, the “lower” group means a “straight or branched group having 1 to 6 carbon atoms”.

When R ¹ is an unsubstituted lower alkyl group, specific examples include a methyl group (related to alanine or a derivative thereof), an ethyl group, a propyl group, and an isopropyl group (related to valine or a derivative thereof). ), A 2-methylpropyl group (related to leucine or a derivative thereof), a 1-methylpropyl group (related to isoleucine or a derivative thereof), n-butyl, n-pentyl,
n-hexyl and the like can be mentioned.

The case where R ¹ is a substituted lower alkyl group means an alkyl group in which a hydrogen atom of the unsubstituted lower alkyl group is substituted by the same or different substituent.
Specific examples of the substituent include a hydroxyl group, a mercapto group optionally substituted with a lower alkyl group, optionally a lower alkyl group, a lower acyl group, an amidino group, N
A mono- or N, N'-di-lower alkylated amidino group, an amino group optionally substituted with a hydroxyl group, a phenyl group optionally substituted with a hydroxyl group, one nitrogen atom in the ring or Examples thereof include a 5-membered polycyclic group having two and optionally a benzene ring optionally condensed, or a carbamoyl group.

Representative examples of the substituted lower alkyl group when the substituent is a hydroxyl group include a hydroxymethyl group (related to serine or a derivative thereof) and a 1-hydroxyethyl group (related to threonine or a derivative thereof). )).

When the substituent is a mercapto group optionally substituted with a lower alkyl group, a typical substituted lower alkyl group is a mercaptomethyl group (related to cysteine or a derivative thereof). , 2-
A methylthioethyl group (related to methionine or a derivative thereof).

The substituent may be a lower alkyl group (preferably a methyl group or an ethyl group), a lower acyl group (preferably a formyl group or an acetyl group), an amidino group [-C (=
NH) -NH _2], N-mono- - or N, N'-di - lower alkylated amidino group (alkyl is preferably methyl, ethyl), substituted lower when substituted by a hydroxyl group is also an amino group Representative examples of the alkyl group include a 4-aminobutyl group (related to lysine or a derivative thereof), 3-amidino (or carbamimidyl:
-C (= NH) -NH ₂₎ associated aminopropyl group (arginine or a derivative thereof.) Can be mentioned.

When the substituent is a phenyl group which may be optionally substituted by a hydroxyl group, typical examples of the substituted lower alkyl group include a phenylmethyl group (related to phenylalanine or a derivative thereof) and 4 -Hydroxyphenylmethyl group (related to tyrosine or derivatives thereof).

The substituent has one or two nitrogen atoms in the ring.
And optionally a benzene ring may be condensed 5
Representative examples of the substituted lower alkyl group when it is a membered heterocyclic group include ( 1H -imidazol-4-yl)
A methyl group (related to histidine or a derivative thereof) and a ( 1H -indol-3-yl) methyl group (related to tryptophan or a derivative thereof).

When the substituent is carbamoyl (—CONH ₂ ), typical examples of the substituted lower alkyl group include a carbamoylmethyl group (related to asparagine or a derivative thereof) and a 2-carbamoylethyl group (glutamine). Or a derivative thereof).

Next, R ² and R ³ independently represent a hydrogen atom, a lower alkyl group or an acyl group. Here, a lower alkyl group has the same meaning as defined for R ¹ . When R ² and R ³ are acyl groups,
It may be a lower acyl group corresponding to the lower alkyl group of R ¹ , or a middle or higher acyl group.

When R ² and R ³ are lower acyl groups, specific examples include a formyl group, an acetyl group and a propionyl group.

When R ² and R ³ are a middle or higher acyl group, these acyl groups may have 7 carbon atoms.
Residues derived from fatty acids having -26.
Such fatty acids are preferably derived from natural lipids, and their origin is rice bran oil wax, lanolin, coconut oil, palm oil, saturated fatty acid such as milk fat,
For example, serotic acid, lignoceric acid, behenic acid, aragic acid, stearic acid, palmitic acid, myristic acid,
Lauric acid, capric acid, caprylic acid, caproic acid, butyric acid, etc., originated from terrestrial animal fats (especially beef tallow), marine animal oils (especially fish liver oil), other vegetable oils (eg, cilantro oil, evening primrose seed oil), etc. Unsaturated fatty acids such as palmitoleic acid, petroselinic acid, oleic acid, elaidic acid, linoleic acid, γ-linolenic acid, and arachidonic acid. Also, these fatty acids are ricinoleic acid, α
-It may have a hydroxyl group like oxylinolenic acid.

It is preferable that R ² and R ³ are hydrogen atoms at the same time.

R ¹ , R ² and R ³ are the same as defined above, except that one of R ² and R ³ and R ¹ together form a nitrogen atom And a residue forming a 5-membered ring together with a carbon atom, for example, a propane-1,3-diyl group (—CH ₂ CH ₂ CH ₂ —)
(Related to proline or a derivative thereof), a 2-hydroxypropane-1,3-diyl group (—CH ₂ CH (O
H) CH ₂ -.) Of (related to 4-hydroxyproline or a derivative thereof), 1-hydroxy-1,3
- diyl group _{(-CH (OH) CH 2 CH} 2 -) may be a (3-hydroxyproline or a derivative thereof associated.).

Specific examples of the α-amino acid or a derivative thereof obtained by the combination of R ¹ , R ² and R ³ include alanine, valine, leucine, isoleucine, serine, threonine, cysteine, methionine, lysine, and the like.
Arginine, phenylalanine, tyrosine, histidine, tryptophan, asparagine, glutamine, proline, 4-hydroxyproline, 3-hydroxyproline and the like.

In the present invention, in addition to the above-mentioned α-amino acid derivatives, one or more of salts or carboxylate thereof or quaternary ammonium compounds thereof are used.

The compound may be a salt via a carboxyl group, especially when one of R ² and R ³ is a lower acyl group, and both R ² and R ³ may be a lower alkyl group. R ² (or R ³ ) when the carboxyl group is an ester (carboxylate)
It may be a salt via an N-group.

[0042] As the ones typical of the salt through a carboxyl group, an ammonium salt or a sodium, alkane metal salts such as lithium or potassium mentioned, R ²
Representative (or R ³ ) N-group-mediated salts include hydrochlorides, hydrobromides, phosphates, sulfates, and organic sulfonates (eg, methanesulfonate, ethanesulfonate) And the like, and organic carboxylate (for example, acetate, citrate, malate, succinate, tartrate, etc.).

Examples of the carboxylic acid esters include esters formed from lower to higher alkanols (eg, methanol, ethanol, octanol, decanol, stearyl alcohol, octacosanol, etc.) and carboxyl groups.

When R ² and R ³ are both a lower alkyl group (preferably a methyl group), a lower alkyl group (preferably a methyl group) is further bonded to the nitrogen atom to which they are bonded to form a quaternary group. A compound forming an ammonium group (N, N, N-trimethylglycine or a derivative thereof is related) may be used.

Among the above compounds, particularly, naturally occurring α-
Those belonging to the category of amino acids can be preferably used, but in the case of α-amino acids other than glycine, L-type amino acid derivatives, their enantiomers (D-type) or their ceramides can also be preferably used. .

The compound of component (B) specified above is compounded with diluents, auxiliaries, and other active substances used in the technical field of medicine or cosmetics as long as the object of the present invention is met. It can be a preparation (agent). Although not limited, typical diluents, auxiliaries, and the like include humectants, surfactants, alcohol, water, buffers, chelating agents, skin activators, and the like.

The compound (B) of the present invention may be used in an amount of 0.001 to 10% by weight depending on the physical properties and physiological activity of the compound.
Can be prepared. The application is mainly by direct application to the skin, but the dose of the component (B) compound can be appropriately adjusted according to the age of the human being treated or the condition of the skin.

If necessary, the cosmetic of the present invention may optionally contain, in addition to the above-mentioned basic components, other components usually used in cosmetics, as long as the desired effects of the present invention are not impaired. it can. Further, not only a single compound but also a combination of two or more of these other components can be used. Specific examples of these other components include, for example,
Hydrocarbons such as liquid paraffin, squalane, petrolatum;
Fats and oils such as macadamia nut oil, olive oil and lanolin; waxes such as jojoba oil, carnauba wax and candelilla wax; silicones such as dimethylpolysiloxane and methylphenylsiloxane; caprylic alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol,
Higher alcohols such as cholesterol and phytosterol; higher fatty acids such as capric acid, myristic acid, palmitic acid, stearic acid, behenic acid, lanolin fatty acid, linoleic acid, and linolenic acid; polyethylene glycol, glycerin, 1,3-butylene glycol, and erythritol ,
Humectants such as sorbitol, xylitol, maltitol, chitosan; cellulose, hydroxyethylcellulose, hydroxypropylcellulose, methylhydroxypropylcellulose, methylcellulose, carboxymethylcellulose, quinceseed, carrageenan, pectin, mannan, curdlan, chondroitin sulfate, starch, galactan , Dermatan sulfate, glycogen,
Gum arabic, heparan sulfate, tragacanth gum, keratan sulfate, chondroitin, xanthan gum, mucoitin sulfate, hydroxyethyl guar gum, carboxymethyl guar gum, guar gum, dextran, kerato sulfate, locust bean gum, succinoglucan, carolinic acid, chitin, chitosan, carboxymethyl Thickeners such as chitin and agar; lower alcohols such as ethanol; antioxidants such as butylhydroxytoluene, tocopherol and phytin;
Antibacterial agents such as benzoic acid, salicylic acid, sorbic acid, alkyl esters of parahydroxybenzoic acid, hexachlorophene, etc., paraaminobenzoic acid-based ultraviolet absorbers, anthranilic acid-based ultraviolet absorbers, salicylic acid-based ultraviolet absorbers, and cinnamic acid-based ultraviolet absorbers, Benzophenone UV absorber, sugar UV absorber, 3- (4'-methylbenzylidene) -d-camphor, 3-benzylidene-d, 1-camphor, urocanic acid, urocanic acid ethyl ester, 2-phenyl-5- Methylbenzoxazole, 2,2'-hydroxy-5-methylphenylbenzotriazole, 2- (2'-hydroxy-5'-t-octylphenyl) benzotriazole, 2- (2'-hydroxy
-5'-methylphenylbenzotriazole, dibenzalazine, dianisoylmethane, 4-methoxy-4'-t-butyldibenzoylmethane, 5- (3,3-dimethyl-2-norbornylidene) -3-pentan-2-one UV absorbers such as glycine,
Amino acids such as alanine, valine, leucine, threonine, phenylalanine, tyrosine, aspartic acid, asparagine, glutamine, taurine, arginine, histidine, and alkali metal salts and hydrochlorides thereof; acyl sarcosine (eg, lauroyl sarcosine sodium), glutathione, citrate Organic acids such as acid, malic acid, tartaric acid and lactic acid; vitamin A and its derivatives, vitamin B ₆ hydrochloride, vitamin B ₆ tripalmitate, vitamin B
₆ Dioctanoate, vitamin B ₂ and its derivatives, vitamin B such as vitamin B ₁₂ , vitamin B ₁₅ and its derivatives, ascorbic acid, ascorbic acid sulfate (salt), ascorbic acid phosphate (salt), ascorbic acid dipalmitate, etc. Vitamin Cs, α-tocopherol, β-tocopherol, γ-tocopherol,
Vitamin E such as vitamin E acetate, vitamin D
, Vitamins such as vitamin H, pantothenic acid, pantethine; nicotinamide, benzyl nicotinate, γ-oryzanol, allantoin, glycyrrhizic acid (salt),
Glycyrrhetinic acid and its derivatives, hinokitiol,
Saponins such as bisabolol, eucalptone, thymol, inositol, saikosaponin, carrot saponin, hemimasaponin, muclodisaponin, pantothenyl ethyl ether, ethinyl estradiol, tranexamic acid, arbutin, cepharanthin, placenta extract, and other various drugs, such as R. japonicus, Extracts of plants such as Clara, Kouhone, Orange, Sage, Yarrow, Zeniaoi, Assembly, Thyme, Touki, Spruce, Birch, Horsetail, Loofah, Malonier, Yukinoshita, Arnica, Lily, Artemisia, Peony, Aloe, Gardenia, Sawara, Pigments, sorbitan monolaurate, sorbitan monopalmitate, sorbitan sesquioleate, sorbitan trioleate, polyoxyethylene sorbitan monolaurate, monostearyl Acid polio Kisechi Ren sorbitan,
Polyethylene glycol monooleate, polyoxyethylene alkyl ether, polyglycol diether, lauroyl diethanol amide, fatty acid isopropanol amide, maltitol hydroxy fatty acid ether,
Alkylated polysaccharides, alkyl glucosides, nonionic surfactants such as sugar esters, stearyltrimethylammonium chloride, benzalkonium chloride, cationic surfactants such as laurylamine oxide, sodium palmitate, sodium laurate, sodium laurate, Anionic surfactants such as potassium lauryl sulfate, alkyl ethanol triethanolamine ether, funnel oil, linear dodecylbenzene sulfate, polyoxyethylene hydrogenated castor oil, maleic acid, and acylmethyltaurine;
An amphoteric surfactant, a neutralizing agent, an antioxidant, a fragrance, purified water and the like can be added.

The dosage form that the cosmetic of the present invention can take is not particularly limited, and examples thereof include an aqueous solution system, a solubilizing system, an emulsifying system, a powder dispersion system, a water-oil two-layer system, a water-oil-powder three-layer system, and the like. The present invention can be applied to cosmetics in general. Also,
Many uses are available for basic cosmetics such as lotions, emulsions, creams, and packs, makeup cosmetics such as lipsticks and foundations, hair products such as shampoos, rinses, hair dyes, and special cosmetics such as sunscreens. Of cosmetics.

[0050]

The present invention will be described below in more detail with reference to examples, but the technical scope of the present invention should not be construed as being limited to these examples. In addition, about the compounding amount, unless otherwise specified, it shows weight%.

First, prior to disclosure of each formulation example, an evaluation method adopted for the cosmetic of the present invention will be described. (Determination test of dullness prevention effect) For each test product, the subjects were women in their 30s and 50s, and 20 subjects in each group applied the test product to the cheeks of the face twice a day (morning and evening), for one month. A continuous use test was performed. After completion of the continuous use test, the effect of improving dullness was evaluated by subject self-assessment and visual sensation evaluation by three beauty technicians. The evaluation items were "improvement of dullness", "improvement of skin transparency", and "improvement of skin whiteness".
It is. The evaluation was divided into four stages of excellent effect (3 points), effective (2 points), slightly effective (1 point), and no effect (0 point), and represented by an average evaluation score between each subject and a beauty technician. .

(Emollient Effect Test) Male Panel 10
A 10% aqueous solution of an activator (aqueous sodium lauryl sulfate) was applied to some parts of the human forearm for 3 days, and the skin was intentionally roughened. Then, the lotion or milky lotion of the sample is applied twice a day. Five days after the start of the application, the condition of the skin surface is measured by a replica method and skin conductance. The emollient effect was evaluated according to criteria and criteria.

[0053]Evaluation criteria  Significant effect: The symptoms of rough skin disappeared. Effective: The symptoms of rough skin have been reduced. Somewhat effective: The symptoms of rough skin have become slightly weaker. Ineffective: No change in symptoms of rough skin is observed. Here, the symptoms of rough skin include (1) exfoliation of stratum corneum and erythema
(2) Skin groove and skin hills are not clear,
It means that the texture is not complete.

[0054]Judgment criteria  ：: The ratio of subjects exhibiting remarkably effective, effective and slightly effective is 8
0% or more. ：: The proportion of subjects showing significant, effective and somewhat effective is 5
0% or more and less than 80%. Δ: The ratio of subjects showing significant, effective and somewhat effective is 3
0% or more and less than 50%. ×: The ratio of subjects showing significant, effective and slightly effective is 3
It is less than 0%.

First, the following Comparative Examples 1 to 5 and Example 1
A lotion having the formulation shown in ~ 5 is prepared by a conventional method,
These test articles were subjected to the above-described dullness-preventing effect test and emollient effect test. Table 1 shows the results.
To Table 6 below.

Compounding amount Comparative example 1 Comparative example 2 Comparative example 3 Comparative example 4 Comparative example 5 Aqueous phase Purified water Residue Residue Residue Residue Residue Carboxoxyvinyl polymer 0.2 0.2 0.2 0.2 0.2 Alkyl-modified carboxylvinyl polymer 0.1 0.1 0.1 0.1 0.1 Fluoropolycarbonate 5.0 5.0 5.0 5.0 5.0 Ethanol 5.0 5.0 5.0 5.0 5.0 DL-alanine − − 3.0 3.0 0.0005 Methyl alcohol Appropriate amount Appropriate amount Appropriate amount Appropriate amount (Composition of clathrate) Human peroxyethylated β-CD-0.95-0.0057 4.75 Macatemia nut oil fatty acid cholesteryl-0.05-0.0003 0.25 B. Oil phase Cetyl isooctanoate 4.0 4.0 4.0 4.0 4.0 2-ethylhexyl p-methoxycinnamate 0.1 0.1 0.1 0.1 0.1 <Production method> Methyl paraben is dissolved in a part of ethanol. This ethanol phase is added to the aqueous phase. Further, hydroxyethylated β-CD is dissolved in a part of purified water, and macadamia nut oil fatty acid cholesteryl is added thereto to form an inclusion. After adding to the aqueous phase, the oil phase is added, and the pre-emulsification is performed. After that, the mixture was further uniformly emulsified with a homomixer to obtain a serum.

Amounts Example 1 Example 2 Example 3 Example 4 Example 5 A. Aqueous phase Purified water Residue Residue Residue Residue Residue Carboxoxyvinyl polymer 0.2 0.2 0.2 0.2 0.2 Alkyl-modified carboxylvinyl polymer 0.1 0.1 0.1 0.1 0.1 Fluoropolycarbonate 5.0 5.0 5.0 5.0 5.0 Ethanol 5.0 5.0 5.0 5.0 5.0 DL-alanine 3.0 3.0 0.01 0.01 5.0 Methyl alcohol Suitable amount Suitable amount Appropriate amount Appropriate amount (composition of clathrate) Human peroxyethylated β-CD 0.95 0.095 4.75 0.095 4.75 Macatemium nut oil cholesteryl fatty acid 0.05 0.005 0.25 0.005 0.25 B. Oil phase Cetyl isooctanoate 4.0 4.0 4.0 4.0 4.0 2-ethylhexyl p-methoxycinnamate 0.1 0.1 0.1 0.1 0.1 <Production method> Methyl paraben is dissolved in a part of ethanol. This ethanol phase is added to the aqueous phase. Further, hydroxyethylated β-CD is dissolved in a part of purified water, and macadamia nut oil fatty acid cholesteryl is added thereto to form an inclusion. After adding to the aqueous phase, the oil phase is added, and the pre-emulsification is performed. After that, the mixture was further uniformly emulsified with a homomixer to obtain a serum.

(1) Evaluation by the subject himself

[Table 1]

[Table 2]

(2) Evaluation by a beauty engineer

[Table 3]

[Table 4]

(3) Emollient effect

[Table 5]

[Table 6]

As shown in Tables 1 to 6, the lotion of each example is excellent in synergy of these components by blending a clathrate in which cholesterol ester is included with alanine and hydroxyalkylated cyclodextrin. It can be seen that it has an excellent emollient effect and also has an excellent effect in improving dullness.

Next, formulation examples of the cosmetic of the present invention will be shown.

Formulation Example 1 Cream (% by weight) (1) Cetyl alcohol 5.0 (2) Stearic acid 3.0 (3) Vaseline 5.0 (4) Squalane 10.0 (5) Glycerol tri 2- Ethyl hexanoate 7.0 (6) Dipropylene glycol 5.0 (7) Glycerin 5.0 (8) Propylene glycol monostearate 1.5 (9) POE (20) Cetyl alcohol ether 1.5 (10 ) Triethanolamine 1.0 (11) Evening primrose oil 1.0 (12) Inclusion composition hydroxypropylated β-CD 0.97 Macadamia nut oil fatty acid cholesteryl 0.03 (13) Serine 0.5 (14) Hydrolysis Eggshell membrane 0.1 (15) Magnesium phosphate ascorbate 2.0 (16) Preservative suitable amount (17) Antioxidant suitable Amount (18) Appropriate amount of fragrance (19) Purified water residue <Production method> Glycerin (humectant) and triethanolamine (alkali) were added to purified water and adjusted to 70 ° C (aqueous phase). Next, the hydroxypropylated β-CD is dissolved in a portion of purified water, and macadamia nut oil fatty acid cholesteryl is added thereto to form an inclusion, and after addition to the aqueous phase,
Next, the oil was heated and dissolved, and a surfactant, a preservative, an antioxidant, and a fragrance were added thereto, and the temperature was adjusted to 70 ° C. This was added to the previous aqueous phase to perform preliminary emulsification. After homogenizing the emulsified particles of this pre-emulsion with a homomixer,
After filtration and cooling, a desired cream was obtained.

Formulation Example 2 Emulsion (% by weight) (1) Cetyl alcohol 1.0 (2) Beeswax 0.5 (3) Vaseline 2.0 (4) Squalane 6.0 (5) Dimethylpolysiloxane 2 0.0 (6) Ethanol 5.0 (7) Glycerin 4.0 (8) 1,3-butylene glycol 4.0 (9) POE (10) Monooleate 1.0 (10) Glycerol monostearate 1.0 (11) Trimethylglycine 2.0 (12) Inclusion composition Hydroxypropylated β-CD 0.95 Macadamia nut oil fatty acid cholesteryl 0.05 (13) DL-alanine 1.0 (14) Cola de Cabaro extract 1.0 (15) Preservatives qs (16) Coloring qs (17) Flavor qs (18) Purified water residue <Production method> Glycerin (moisturizing) in purified water ) And a coloring agent, and the mixture was heated and adjusted to 70 ° C. (aqueous phase). Next, the hydroxypropylated β-CD was dissolved in a portion of purified water, and macadamia nut oil fatty acid cholesteryl was added thereto to form an inclusion, which was added to the aqueous phase. Next, a surfactant and a preservative were added to the oil, and the temperature was adjusted to 70 ° C. by heating. This is added to the previous aqueous phase to carry out preliminary emulsification, ethanol is added to this pre-emulsion, and the mixture is stirred. After homogenizing the emulsified particles with a homomixer, deaeration, filtration and cooling are carried out. An emulsion was obtained.

[Formulation Example 3] Foundation (% by weight) (1) Talc 3.0 (2) Titanium dioxide 5.0 (3) Bengala 0.5 (4) Yellow iron oxide 1.4 (5) Black iron oxide 0.1 (6) polyoxyethylene sorbitan monostearate 0.9 (7) triethanolamine 1.0 (8) propylene glycol 5.0 (9) hydroxyethyl cellulose 0.5 (10) acetylated hyaluronic acid 5 (11) Serine 0.5 (12) Stearic acid 2.2 (13) Isohexadecyl alcohol 7.0 (14) Inclusion composition Hydroxypropylated β-CD 0.93 Macadamia nut oil fatty acid cholesteryl 0.07 ( 15) Glycerin monostearate 2.0 (16) Liquid lanolin 2.0 (17) Liquid paraffin 8.0 (18) Preservative The amount (19) Perfume Appropriate amount (20) were uniformly dissolved Purified water Balance <Process> the aqueous phase component at 70 ° C., was then dissolved hydroxypropylated beta-CD in a portion of purified water,
To this, macadamia nut oil fatty acid cholesteryl was added to make an inclusion, and added to the aqueous phase. The powder components sufficiently mixed and pulverized were added thereto with stirring, and homomixer treatment was performed at 70 ° C. This was cooled while stirring, and the system was cooled to 45 ° C.
At the time, the flavor was added, finally degassed and filled into a container to obtain a desired foundation.

[0066]

As described above, according to the present invention, a skin external preparation having a high emollient effect on the skin and an excellent effect of preventing dullness can be obtained.

Continued on the front page F term (reference) 4C083 AA122 AB232 AB242 AB432 AC012 AC022 AC092 AC102 AC122 AC182 AC232 AC242 AC342 AC352 AC402 AC422 AC482 AC542 AC581 AC582 AC661 AC691 AC902 AD092 AD152 AD251 AD252 AD282 AD332 AD412 AD491 AD492 AD512 CC02 DD33 EE12

Claims (6)

[Claims] (1) The following (A) and (B) are used as active ingredients.
An external preparation for skin, characterized by comprising: (A) hydroxyalkylated cyclodextrin
Cholesterol ester containing sterol ester
Clathrate (B) Formula (I) below (Where R¹Represents a hydrogen atom or a straight chain having 1 to 6 carbon atoms.
Or branched (hereinafter, a "straight or branched chain having 1 to 6 carbon atoms")
Are simply referred to as "lower" groups. ) Unsubstituted or substituted alkyl
R^TwoAnd R^ThreeIs independently of each other a hydrogen atom,
Represents a lower alkyl group or an acyl group. )
α-amino acid derivative, salt thereof or carboxylic acid ester
And its quaternary ammonium (provided that R^Twoand
R^ThreeIs a lower alkyl group. )
One or more compounds 2. The aforementioned R ¹ is a substituted alkyl group, and the substituent is a hydroxyl group, a mercapto group (which may be substituted with a lower alkyl group), an amino group (however, a lower alkyl group or a lower acyl group). Group, amidino group, N-mono- or N, N'-di-lower alkylated amidino group, or substituted with hydroxyl group), phenyl group (provided that
It may be substituted with a hydroxyl group. ), A 5-membered heterocyclic group having one or two nitrogen atoms in the ring (provided that a benzene ring may be condensed), or a carbamoyl group. External preparation for skin. 3. The method according to claim ² , wherein R ¹ , R ² and R ³ are R ² and R
Any one of ³ and R ¹ together form propane-
1,3-diyl group or 2-hydroxypropane-1,
2. The external preparation for skin according to claim 1, wherein the external preparation forms a 3-diyl group. 4. The compounding amount of the component (A) is from 0.01 to
20.0% by weight, the amount of the component (B) is 0.00
The skin external preparation according to any one of claims 1 to 3, wherein the amount is 1 to 10.0% by weight. 5. The method according to claim 1, wherein the cholesterol ester clathrate has a hydroxyalkylated cyclodextrin to cholesterol ester ratio of 99: 1 to 90:10. External preparation for skin. 6. The external preparation for skin according to claim 1, wherein the emulsion type is an oil-in-water type.