JP2008001654A - External preparation for skin - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an external preparation for skin having excellent moisture-retaining and skin-balancing effect and effect to improve spot and wrinkle. <P>SOLUTION: The external preparation is produced by adding ubiquinone and a specific N-acyl acidic amino acid ester to an amino acid and an amino acid derivative (excluding N-acyl acidic amino acid ester). <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to an external preparation for skin, and more particularly, to an external preparation for skin having excellent moisturizing effect and skin conditioning effect, and excellent effect of improving stains (stains) and wrinkles.

  Since amino acids and amino acid derivatives have a moisturizing action, skin external preparations containing them have been proposed. However, sufficient amino acid and amino acid derivatives alone do not always provide a sufficient moisturizing effect.

  Further, since ubiquinone has a skin conditioning action and a skin activation action, an external preparation for skin containing ubiquinone has also been proposed, but there is a problem that sufficient characteristics cannot always be obtained with ubiquinone alone.

  Therefore, it has been proposed to use ubiquinone and a vitamin A derivative in combination to adjust a skin external preparation (Patent Document 1), or to use ubiquinone and a moisturizing component in combination to adjust a moisturizing cosmetic. (Patent Document 2).

However, even with them, a skin external preparation excellent in moisturizing effect and skin conditioning effect and excellent in improving stains and wrinkles could not be obtained.
Japanese Patent Publication No. 2002-513746 JP 2004-99564 A

  An object of the present invention is to solve the above-described problems of the prior art, and to provide an external preparation for skin which is excellent in moisturizing effect and skin conditioning effect and excellent in improving stains and wrinkles.

  The present invention is a skin excellent in moisturizing effect and skin conditioning effect and excellent in improving stains and wrinkles by blending ubiquinone and N-acyl acidic amino acid ester in addition to blending amino acid or amino acid derivative. An external preparation was provided to solve the previous issues.

  Furthermore, the present invention is excellent in moisturizing effect and skin conditioning effect, and in improving blemishes and wrinkles, by adding pyridoxylserine in addition to the amino acid or amino acid derivative, ubiquinone and N-acyl acidic amino acid ester. In addition to the above properties, the present invention provides an external preparation for skin with further improved stability.

  In the present invention, in addition to blending an amino acid or an amino acid derivative, by adding ubiquinone and an N-acyl acidic amino acid ester, it is excellent in moisturizing effect and skin conditioning effect, and has an excellent effect of improving stains and wrinkles An agent can be provided. Furthermore, in the present invention, by adding pyridoxylserine in addition to them, it is possible to provide an external preparation for skin that further enhances stability while maintaining the above characteristics.

  Hereinafter, the present invention will be described in detail. In the present invention, an amino acid or an amino acid derivative is blended in an external preparation for skin to contribute to the improvement of the moisturizing effect. Examples of the amino acid include alanine, arginine, asparagine, aspartic acid, citrulline, cysteine, and cystine. , Glutamine, glutamic acid, glycine, histidine, oxyproline, isoleucine, leucine, lysine, methionine, ornithine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, valine, etc., their L-form, D-form or DL-form Any of these may be sufficient, and those salts may be sufficient. Examples of such salts include sodium salt, potassium salt, triethanolamine salt, zinc salt and the like.

  Examples of the amino acid derivatives include those obtained by cyclization, acylation or esterification of the above-mentioned amino acids, such as acetyl glutamic acid, acetyl methionine, acetyl cysteine, N, N-diacetyl-L-cystine dimethyl ester, pyrrolidone carboxyl. Acid salts, acyl glutamate salts, acyl glycine salts, acyl alanine salts, acyl arginine ethyl ester salts and the like. Examples of the salt include sodium salt, potassium salt, triethanolamine salt, zinc salt and the like. Of these, N, N-diacetyl-L-cystine dimethyl ester and pyrrolidone carboxylic acid zinc salt are preferred. However, N-acyl acidic amino acid esters are excluded.

  The above amino acids or amino acid derivatives may be used alone or in combination of two or more.

  In the present invention, the amino acid or amino acid derivative is preferably 0.001% by mass or more, and 0.01% by mass or more, in the external preparation for skin, in order to appropriately express the effect. More preferably, it is more preferably 0.1% by mass or more, and if the compounding amount of the amino acid or amino acid derivative is increased more than necessary, there is a possibility that crystals are precipitated. It is preferable to make it 20% by mass or less, more preferably 10% by mass or less.

The ubiquinone for use in the present invention, a 2,3-dimethoxy-5-methyl-6-polyprenyl-1,4-ubiquinones isoprene units in the side chain is 10 benzoquinone, known as ubidecarenone or coenzyme _{Q 10} This ubiquinone contributes to the improvement of skin conditioning and the improvement of blemishes and wrinkles, but in order to express its effects appropriately, the compounding amount is It is preferably 0.0001% by mass or more, more preferably 0.01% by mass or more, further preferably 0.03% by mass or more, and when the amount of ubiquinone is increased more than necessary. , Since there is a risk of crystallization or yellowing of the product color, it is preferably 10% by mass or less, more preferably 1% by mass or less. It is more preferable to set it to mass% or less.

The N-acyl acidic amino acid ester used in the present invention has the following chemical formula (I)
(Wherein X and Y may be the same or different, X and Y are ester-forming residues of sterols, linear or branched liquid higher alkyl alcohols or alkenyl alcohols having 8 to 30 carbon atoms, or It is at least one selected from ester-forming residues of solid linear or branched higher alcohols having 12 to 38 carbon atoms, and COR bonded to the nitrogen atom is a linear acyl group having 8 to 22 carbon atoms. N is 1 or 2. a and b are 0 to 10, and b is 0 to 10.)
N-acyl acidic diesters are particularly preferred, and suitable specific examples thereof include, for example, N-lauroyl glutamate (cholesteryl / behenyl / octyldodecyl), N-lauroyl glutamate di (cholesteryl / Octyldodecyl), N-lauroylglutamate di (phytosteryl / 2-octyldodecyl), N-lauroylglutamate di (octyldodecyl / phytosteryl / behenyl) and the like from Ajinomoto Co., Inc., respectively. 301 "," L-Du CL-202 "," L-Du PS-203 ", and" L-Du PS-304 ".

  And in this invention, this N-acyl acidic amino acid ester contributes to the improvement of moisture retention and skin conditioning property, and also contributes to the improvement of stability by the combined use with ubiquinone. In order to achieve expression, the blending amount is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, further preferably 0.5% by mass or more, If the amount of N-acyl acidic amino acid ester is increased more than necessary, there is a risk of stickiness, so it is preferably 20% by mass or less, more preferably 10% by mass or less, and 5% by mass or less. More preferably.

  The skin external preparation of the present invention contains the above-mentioned essential compounding by using the above-mentioned amino acid or amino acid derivative, ubiquinone, N-acyl acidic amino acid ester as an essential compounding component, and further adding pyridoxylserine below them. Without reducing the effects of the components, the stability as an external preparation for skin can be further improved by suppressing the decrease in stability based on the reactivity of the amino acid or amino acid derivative.

This pyridoxylserine has the following chemical formula (II)
In order to appropriately express the effect, the blending amount is preferably 0.001% by mass or more, more preferably 0.01% by mass or more, and 0.05% by mass or more. It is more preferable that the amount of pyridoxylserine is increased more than necessary, so that there is a risk of crystallization or yellowing of the product color. % Or less, more preferably 1% by mass or less.

  The skin external preparation of the present invention contains the above-mentioned amino acid or amino acid derivative, ubiquinone, N-acyl acidic amino acid ester in water or an aqueous liquid mainly containing water (containing 10% by mass or more of water). In addition to these, it is adjusted by blending pyridoxylserine, but in addition to these, in a range that does not impair their effects, a blending agent generally called a skin external preparation base, such as alcohol, sequestering metal ions Agents, thickeners, oils, chemicals, fragrances, colorants, ultraviolet absorbers, surfactants, preservatives, and the like can be blended.

  Examples of the alcohol include monovalent alcohols such as ethanol and isopropanol, divalent alcohols such as ethylene glycol, propylene glycol, 1,3-butylene glycol, and 1,2-pentanediol, trivalent alcohols such as glycerin, Examples include tetravalent alcohols such as pentaerythritol, pentavalent alcohols such as xylitol, hexavalent alcohols such as sorbitol and mannitol, and sugar alcohols such as maltol, xylitol, and amylolytic sugar-reducing alcohol.

  Examples of the emulsifier include POE sorbitan fatty acid esters such as POE (POE = polyoxyethylene, hereinafter the same) -sorbitan monooleate, POE-sorbitan monostearate, POE-sorbitan monooleate, POE-sorbitan tetraoleate, POE-sorbite fatty acid esters such as POE-sorbitol monolaurate, POE-sorbitol monooleate, POE-sorbitol pentaoleate, POE-sorbitol monostearate, POE-glycerol monostearate, POE-glycerol monoisostearate POE-glycerin fatty acid esters such as POE-glycerin triisostearate, POE-monooleate, POE-distearate, POE-monodiolate, stearic acid ester POE-fatty acid esters such as lenglycol, POE-alkyl ethers such as POE-lauryl ether, POE-oleyl ether, POE-stearyl ether, POE-behenyl ether, POE-2-octyldodecyl ether, POE-cholestanol ether , POE-octylphenyl ether, POE-nonylphenyl ether, POE-alkylphenyl ethers such as POE-dinonylphenyl ether, proalonic types such as brulon, POE · POP (POP = polyoxypropylene, the same applies hereinafter) -cetyl PO such as ether, POE · POP-2-decyltetradecyl ether, POE · POP-monobutyl ether, POE · POP-hydrogenated lanolin, POE · POP-glycerin ether POP-alkyl ethers, POE-castor oil, POE-hardened castor oil, POE-hardened castor oil monoisostearate, POE-hardened castor oil triisostearate, POE-hardened castor oil monopyroglutamic acid monoisostearic acid diester POE-castor oil-hardened castor oil derivatives such as POE-hardened castor oil maleic acid, POE-beeswax lanolin derivatives such as POE-sorbit beeswax, sucrose fatty acid ester, trioleyl phosphate and the like.

  Examples of sequestering agents include 1-hydroxyethane-1,1-diphosphonic acid, 1-hydroxyethane-1,1-diphosphonic acid tetrasodium salt, disodium edetate, trisodium edetate, tetrasodium edetate, Examples include sodium citrate, sodium polyphosphate, sodium metaphosphate, and gluconic acid.

  Examples of thickeners include gum arabic, carrageenan, gum karaya, gum tragacanth, carob gum, quince seed, casein, dextrin, gelatin, sodium pectate, sodium alginate, methylcellulose, ethylcellulose, carboxymethylcellulose (CMC), hydroxyethylcellulose, hydroxyethyl Cellulol, hydroxypropyl cellulose, polyvinyl alcohol (PVA), polyvinyl methyl ether (PVM), polyvinyl pyrrolidone (PVP), sodium polyacrylate, carboxyvinyl polymer, locust bean gum, guar gum, tamarin gum, dialkyldimethylammonium cellulose sulfate Xanthan gum, magnesium aluminum silicate, bentonite, hectorite, etc.

  Examples of oils include avocato oil, camellia oil, turtle oil, macadamia nut oil, corn oil, mink oil, olive oil, rapeseed oil, egg yolk oil, sesame oil, persic oil, wheat germ oil, sasanqua oil, castor oil, flaxseed oil, saury Flower oil, cottonseed oil, eno oil, soybean oil, peanut oil, tea seed oil, kaya oil, rice bran oil, cinnagiri oil, Japanese kiri oil, jojoba oil, germ oil, triglycerin, trioctanoic acid glycerin, triisopalmitic acid glycerin, etc. Liquid oil, fat, cacao butter, palm oil, horse fat, hydrogenated palm oil, palm oil, beef tallow, hydrogenated beef tallow, palm kernel oil, pork fat, beef bone fat, owl kernel oil, hydrogenated oil, cow leg oil, molasses , Solid fats such as hardened castor oil, beeswax, candelilla wax, cotton wax, carnauba wax, bayberry wax, ibota wax, whale wax, montan wax, nuka wax, Waxes such as Norin, Kapok wax, Lanolin acetate, Liquid lanolin, Sugar cane wax, Lanolin fatty acid isopropyl, Hexyl laurate, Shellac wax, POE-lanolin alcohol acetate, POE-cholesterol ether, lanolin fatty acid polyethylene glycol, POE-hydrogenated lanolin alcohol ether , Hydrocarbons such as liquid paraffin, ozokerite, squalene, pyristan, puffafin, ceresin, squalane, petrolatum, microcrystalline wax and the like.

  And the dosage form of the external preparation for skin of this invention is not specifically limited, For example, any of liquid form, emulsion, gel form, cream form, and suspension form may be sufficient. The external preparation for skin of the present invention is usually used for skin other than the scalp called skin, but may be used for the scalp.

  Next, the present invention will be described more specifically with reference to examples. However, the present invention is not limited to only these examples.

Examples 1-2 and Comparative Examples 1-3
Five cream type skin external preparations were prepared with the compositions shown in Table 1. The amount of each component in the table is expressed in mass%, and the remainder indicating the amount of purified water refers to the amount required to make the whole 100 mass%. And when they show a compounding quantity in a following example and a comparative example, they are the same. In Examples 1 and 2 and the like, the N-acyl acidic amino acid ester contains 0.8% by mass of four types of mixtures. The breakdown is as follows.
Breakdown of N-acyl acidic amino acid esters:
There are the following four types, and the amount is 0.2% by mass, and the total is 0.8% by mass.
N-lauroyl glutamate di (phytosteryl 2-octyldodecyl)
N-Lauroylglutamate di (Okitildodecyl / Phytosteryl / Behenyl)
N-lauroylglutamate di (cholesteryl / behenyl / octyldodecyl)
N-lauroylglutamate di (cholesteryl / octyldodecyl)

About 50 mg of the topical skin preparations of Examples 1 and 2 and Comparative Examples 1 to 3 prepared as described above were each applied to the eyes of 10 professional panelists twice a day for 4 weeks. The effect, the improvement effect on the stain, and the improvement effect on the wrinkle were evaluated. The evaluation is shown in Table 1. Evaluation is scored in five levels according to the following criteria, and when displayed in Table 1, the average score is 4 or more: ◎ 3 or more but less than 4 ○, 2 or more but less than 3 Was symbolized as x.
Evaluation criteria:
The effect was remarkable ... 5 points The effect was ... 4 points The effect was slightly ... 3 points The effect was not felt ... 2 points was deteriorated ... ... 1 point

  Moreover, stability was evaluated by the method shown below about the skin external preparation of the said Examples 1-2 and Comparative Examples 1-3. The results are also shown in Table 1.

Stability evaluation method:
After putting the skin external preparations of Examples 1-2 and Comparative Examples 1-3 in separate glass containers and storing them at 50 ° C. for 30 days, the presence or absence of discoloration is visually observed, and the lid of the glass container is taken. The smell was checked and the presence or absence of a strange odor was examined. In the display of the results in Table 1, when there is an obvious discoloration or odor, ×, when there is discoloration or odor, Δ, when there is very little discoloration or odor, Those that do not change are symbolized as ◎.

  As is clear from Table 1, in addition to amino acids (L-arginine, glycine, alanine, L-serine and L-proline), amino acid derivatives (zinc pyrrolidone carboxylate), ubiquinone and N-acyl acidic amino acid ester were blended. Example 1 was excellent in moisturizing effect and skin conditioning effect, excellent in improving stains and wrinkles, and improved in stability as compared with Comparative Example 1 in which no N-acyl acidic amino acid ester was blended. .

  And, in addition to each component of Example 1, Example 2 further blended with pyridoxylserine is excellent in the moisturizing effect and skin conditioning effect as well as in Example 1, and is excellent in the effect of improving stains and wrinkles. The stability was further improved from that of Example 1.

  In contrast, Comparative Example 1 in which an amino acid and ubiquinone were blended but no N-acyl acidic amino acid ester was blended did not have sufficient moisturizing effect and skin conditioning effect, and had poor stability, In Comparative Example 2 in which an amino acid and an N-acyl acidic amino acid ester were blended, but no ubiquinone was blended, the effect of improving stains and wrinkles was not sufficient, and the stability was inferior to that of the Examples. It was.

  And although the comparative example 3 which does not mix | blend an amino acid and pyridoxyl serine but does not mix | blend ubiquinone or N-acyl acidic ester, all of the moisturizing effect, the skin conditioning effect, and the improvement effect with respect to a spot and a wrinkle are enough. There wasn't.

Example 3
A skin lotion type skin external preparation was prepared with the following composition.
mass%
L-serine 1.0
L-sodium aspartate 1.0 DL-pyrrolidone sodium carboxylate 1.0
Trimethylglycine 1.0
N-coconut oil fatty acid acyl-L-arginine 0.1
DL-pyrrolidone carboxylate ubiquinone 0.03
N-lauroylglutamate di (octyldodecyl 1.0
/ Phytosteryl / Behenyl) (Brand name "El Dew PS-304")
Pyridoxyl serine 0.05
Glycerin 10.0
1,3-butylene glycol 5.0
Polyoxyethylene hydrogenated castor oil 1.0
Pyroglutamic acid isostearic acid diester phenoxyethanol 0.2
Methylparaben 0.1
Ethanol 3.0
Hydroxyethyl cellulose 0.05
Perfume Appropriate amount of purified water

Example 4
An emulsion type skin external preparation was prepared with the following composition.
mass%
Acetylcysteine 0.1
Valine 0.1
Leucine 0.1
Isoleucine 0.1
Ubiquinone 0.01
N-lauroylglutamate di (cholesteryl / behenyl 1.0
/ Octildodecyl) (Brand name "El Deu CL-301")
N-lauroyl glutamate di (phytosteryl 0.5
/ 2-octyldodecyl) (Brand name "El Dew PS-203")
Pyridoxyl serine 0.1
Flowing ballaffin 7.0
Squalane 5.0
Isocetyl myristate 3.0
Cetanol 0.5
Monostearic acid POE (20) sorbitan 2.5
Xanthan gum 0.1
Dimethicone 4.0
Concentrated glycerin 5.0
Phenoxyethanol 0.2
Dipotassium glycyrrhizinate 0.1
dl-α-tocopherol 0.1
Oil-soluble licorice extract 0.01
Purified water residue

Example 5
A cream type skin external preparation was prepared with the following composition.
mass%
L-Arginine 0.5
L-lysine 0.1
L-glutamic acid 0.1
L-tryptophan 0.1
L-histidine 0.05
L-serine 1.0
Ubiquinone 0.1
N-lauroylglutamate di (cholesteryl 2.0)
/ Octildodecyl) (Brand name "El Deu CL-202")
Pyridoxyl serine 0.1
Jojoba oil 3.0
Squalane 5.0
Vaseline 5.0
Behenyl alcohol 2.0
Tetraoleic acid POE (20) Sobitan 3.0
Lauroyllysine 1.0
Carboxyvinyl polymer 0.5
Glyceryl monostearate 1.0
Sodium hyaluronate 0.01
Perfume Appropriate amount of pigment Appropriate amount of purified water

  About the external preparations for skin of Examples 3 to 5 above, their moisturizing effect, skin conditioning effect, improvement effect against stains and wrinkles, and stability were examined in the same manner as in Example 1. As in Examples 1 and 2, Both were good.

Claims (4)

A skin external preparation comprising an amino acid and an amino acid derivative (excluding an N-acyl acidic amino acid ester), wherein ubiquinone and an N-acyl acidic amino acid ester are used in combination. The amount of amino acid or amino acid derivative (excluding N-acyl acidic amino acid ester) is 0.001% by mass to 50% by mass, the amount of ubiquinone is 0.0001% by mass to 10% by mass, N— The skin external preparation according to claim 1, wherein the amount of the acyl acidic amino acid ester is 0.01 mass% or more and 20 mass% or less. The external preparation for skin according to claim 1 or 2, wherein pyridoxylserine is blended. The external preparation for skin according to claim 3, wherein the amount of pyridoxylserine is 0.0001 to 5% by mass.