JP4669228B2 - Skin preparation for external use - Google Patents

Description

  The present invention relates to a skin external preparation composition, and more particularly to a skin external preparation composition capable of preventing or improving wrinkles, rough skin, tanned skin, and aging skin while maintaining skin firmness and moisture.

  Hyaluronic acid retains moisture in the interstitial space, retains cells based on the formation of a jelly-like matrix in the tissue, maintains tissue lubricity and flexibility, resists external forces such as mechanical failure, and And has many functions such as prevention of bacterial infection (see Non-Patent Document 1).

  On the other hand, the hyaluronic acid staining intensity between epidermal cells decreases due to aging (see Non-Patent Document 2), and almost no hyaluronic acid is detected in the optical elasticity fibrosis due to ultraviolet irradiation (Non-Patent Documents 3 to 4). As a result, it is thought to cause dryness, firmness, loss of elasticity, and an increase in wrinkles. In order to improve such a state, a method of keeping the skin surface moisturized by applying a cosmetic containing hyaluronic acid has been taken, but since hyaluronic acid, which is a polymer, does not penetrate the skin, it is fundamentally Improvement cannot be expected. Therefore, it is expected to develop a substance that fundamentally improves the skin function by enhancing the hyaluronic acid synthesizing ability inherent in the cell itself.

  On the other hand, when the present applicant applied one or more compounds selected from the group consisting of N-methyl-L-serine, ethanolamine, N-methylethanolamine, or salts thereof to the skin, It has been confirmed that it can pass through the basement membrane and reach the dermal layer (connective tissue) where fibroblasts are present, and promotes the hyaluronic acid production ability of fibroblasts (see Patent Document 1). Further, N-acetylglucosamine has been found to increase the amount of hyaluronic acid in the normal stratum corneum (see Patent Document 2), but further improvement of the effect has been desired.

“BIO INDUSTRY”, 1991, Vol. 8, p. 346 “J. Invest. Dermatol”, 1994, Vol. 102, p. 385 “Skin (increased by 5)”, 1997, Vol. 51, p. 53 “Nagoya Med. J.”, 1997, Vol. 41, p. 27 Japanese Patent No. 3073862 Japanese Patent Laid-Open No. 2001-2551

  Therefore, the present invention can fundamentally improve the skin function by enhancing the hyaluronic acid synthesizing ability inherent in the cell itself, and keeps the skin firm and moisturized to prevent wrinkles, rough skin, tanned skin and aging skin. Alternatively, an object of the present invention is to provide a skin external preparation composition that can be improved.

As a result of intensive studies aimed at solving the above-mentioned problems, the present inventors have prepared an external preparation for skin containing 3-methylcyclopentadecanone or an extract or essential oil obtained from Crocus sativus. In the product, (A) one or more dermal hyaluronic acid production promoters selected from 3-methylcyclopentadecanone, N-methyl-L-serine or a salt thereof, and (B) Crocus saffron (Crocus) sativus) extract or essential oil, and one or more epidermal hyaluronic acid production promoters selected from N-acetylglucosamine in combination to maintain synergistically superior skin firmness and moisture As a result, it has been found that an effect of preventing or improving wrinkles, dry skin, tanned skin, and aging skin can be obtained, and the present invention has been completed.

  That is, the present invention relates to (A) one or more dermal hyaluronic acid production promoters selected from 3-methylcyclopentadecanone, N-methyl-L-serine or a salt thereof, and (B) Iridae Crocus saffron. (Crocus sativus), an extract or essential oil, one or more epidermal hyaluronic acid production promoters selected from N-acetylglucosamine, and 3-methylcyclopentadecanone or Iridae crocus saffron (Crocus sativus) It is in the skin external preparation composition characterized by using the extract or essential oil obtained as an essential component.

  The present invention increases the production amount of hyaluronic acid in the epidermis layer and dermis layer, and synergistically excels in preventing or improving wrinkles, dry skin, tanned skin, and aging skin while maintaining skin firmness and moisture. A skin external preparation composition can be obtained.

  Hereinafter, the configuration of the present invention will be described in detail.

  3-methylcyclopentadecanone used in the present invention is a known compound. It is the main aroma component of natural musk and is contained in an amount of 0.5 to 2.0%. Discovered by Walbaum in 1906. In 3-methylcyclopentadecanone, (R)-(−)-3-methylcyclopentadecanone and (S)-(+)-3-methylcyclopentadecanone exist as optically active substances. The natural type is (R)-(−)-3-methylcyclopentadecanone. In the present invention, (R)-(−)-3-methylcyclopentadecanone is preferably used.

  The method for producing 3-methylcyclopentadecanone used in the present invention is not particularly limited. It may be isolated from a natural product, and can be obtained by synthesis by a cyclization reaction, ring expansion reaction, or the like, or an optically active substance resolution method.

  The content of 3-methylcyclopentadecanone used in the present invention in the external preparation for skin varies depending on the form and cannot be specified unconditionally, but based on the total amount of the external preparation for skin, 0.0000001 To 0.01% by mass (hereinafter simply referred to as%) is preferable, and 0.00001 to 0.001% is more preferable. However, in the case of a thing diluted at the time of use like a bath agent, the content can be further increased.

  Further, N-methyl-L-serine or a salt thereof used in the present invention is a known compound, and its production method is not particularly limited, and a commonly used method may be used. In the present invention, these compounds may be used alone or in combination of two or more.

The content of N-methyl-L-serine or a salt thereof used in the present invention in the skin external preparation composition varies depending on the form and cannot be defined unconditionally, but based on the total amount of the skin external preparation composition, 0.001 to 3% is preferable, and 0.01 to 0.1% is more preferable. However, in the case of a thing diluted at the time of use like a bath agent, the content can be further increased.

  Since 3-methylcyclopentadecanone and N-methyl-L-serine or a salt thereof used in the present invention are low molecules, when applied to the skin, they pass through the epidermal layer and the basement membrane, and fibroblasts It is possible to reach the dermis layer (connective tissue) in which fibroblasts exist, which is advantageous in promoting the ability of fibroblasts to produce hyaluronic acid.

  Crocus sativus used in the present invention is a plant distributed in the northern hemisphere and gives purple flowers in autumn. The extract or essential oil obtained from this plant may be obtained from the whole flower or the female head. The extract can be obtained by a solvent extraction method, a liquefied gas extraction method such as liquefied carbon dioxide gas or liquefied butane gas, or a supercritical gas extraction method. Solvents used here include water or alcohols such as methanol, ethanol and isopropyl alcohol, polyhydric alcohols such as ethylene glycol, propylene glycol and 1,3-butylene glycol, ketones such as acetone, and esters such as ethyl acetate. , Ethers such as diethyl ether, aromatic compounds such as hexane, pentane and benzene can be selected from one kind alone or a mixture of two or more kinds. The essential oil can be obtained by the above method or steam distillation.

  Further, the extract or essential oil obtained from Crocus sativus used in the present invention may remain as an extraction solvent solution or as a steam distillate, or may be concentrated, dried and filtered by a conventional method. Re-extraction or the like may be performed.

  The content of the extract or essential oil obtained from Crocus sativus used in the present invention in the skin external preparation composition varies depending on the form and cannot be generally defined, but the skin external preparation composition 0.000001 to 0.01% in terms of dry solid content, preferably 0.00001 to 0.001%, based on the total amount. However, in the case of a thing diluted at the time of use like a bath agent, the content can be further increased.

  N-acetylglucosamine used in the present invention is not limited to any product such as a synthetic product, a fermentation product, a degradation product obtained from chitin degradation such as crabs and shrimp.

  The content of N-acetylglucosamine used in the present invention in the external preparation for skin is preferably 0.001 to 10%, particularly preferably 0.01 based on the total amount of the external preparation for skin. ~ 5%.

  The form of the external composition for skin of the present invention may be any of liquid, solid or semi-solid, preferably ointment, gel, cream, spray, patch, lotion, packs, emulsion, powder, toilet, Examples include foaming agents, perfumes and bathing agents.

In addition to the above, the skin external preparation composition of the present invention includes tar pigments, colored pigments such as iron oxide, preservatives such as parabens and phenoxyethanol, silicon such as dimethylpolysiloxane, methylphenylpolysiloxane, and cyclic silicon. Oils, hydrocarbons such as paraffin, petroleum jelly, olive squalane, rice squalane, rice germ oil, jojoba oil, sunflower oil, safflower oil, olive oil, macadamia nut oil, sunflower oil and other vegetable oils, wax such as beeswax, moscow and carnauba wax , Octyldodecyl myristate, cetyl palmitate, isostearyl isostearate, isopropyl myristate, etc., lower alcohols such as ethanol, higher alcohols such as cetanol, behenyl alcohol, stearyl alcohol, long-chain branched aliphatic alcohols, Sterols and derivatives such as terol, phytosterol, branched fatty acid cholesterol ester, macadamia nut fatty acid phytosteryl ester, processing oil such as hardened oil, stearic acid, myristic acid, isostearic acid, oleic acid, isoform long chain fatty acid, anteisoform length Higher fatty acids such as chain fatty acids, terpenes such as limonene and hydrogenated bisabolol, triglycerides such as tricapryl / glyceryl caprate, glyceryl 2-ethylhexanoate, triiso type long chain fatty acid glyceryl, glyceryl tripalmitate, sodium cetyl sulfate, N -Anionic surfactants such as stearoyl-L-glutamate, polyoxyethylene alkyl ether, polyoxyethylene fatty acid ester, polyoxyethylene polyhydric alcohol fatty acid ester, Nonionic surfactants such as oxyethylene hydrogenated castor oil, polyhydric alcohol fatty acid ester, polyglycerin fatty acid ester, modified silicon and sucrose ester, cationic surfactants such as tetraalkylammonium salt, betaine type, sulfobetaine type , Amphoteric surfactants such as sulfoamino acid type, natural surfactants such as lecithin, lysophosphatidylcholine, ceramide, cerebroside, pigments such as titanium oxide and zinc oxide, antioxidants such as dibutylhydroxytoluene, sodium chloride , Magnesium chloride, sodium sulfate, potassium nitrate, sodium sulfate, sodium metasilicate, calcium chloride and other inorganic salts, sodium citrate, potassium acetate, sodium oxalate, sodium aspartate, sodium lactate, dichloroacetic acid, mevalonic acid, glycy Organic acids such as luricinic acid and salts thereof, ethanolamine hydrochloride, ammonium nitrate, arginine hydrochloride, diisopropylamine salts, organic amines such as urea and decarboxycarnosine and salts thereof, chelating agents such as edetic acid, xanthan gum, carboxyvinyl polymer, Carrageenan, pectin, alkyl-modified carboxyvinyl polymer, thickeners such as agar, neutralizers such as potassium hydroxide, diisopropanolamine, triethanolamine, UV absorbers such as hydroxymethoxybenzophenone sulfonate, dipropylene glycol, 1,3-butylene glycol, glycerin, propylene glycol, sorbitol, malbitol, diglycerin, raffinose and other polyhydric alcohols, various amino acids, ascorbic acid, biotin, tocopherol, etc. Vitamins and ascorbic acid sulfuric acid ester salts, ascorbic acid phosphate ester salts, can be appropriately blended as vitamin derivative tocopherol nicotinate, etc. to the extent that achieving the object of the present invention.

  Furthermore, keratinization of hyaluronic acid degradation inhibitors such as poppy medallion extract, cricket extract, black river extract, mockin extract, asenyaku extract, clove extract, diisopropylamine dichloroacetic acid, niacin, mevalonic acid, hot spring water, sodium metasilicate, etc. Preventing rough skin and wrinkles by blending accelerators, barrier enhancers such as β-hydroxy-γ-aminobutyric acid, mevalonic acid, and moisturizers such as hyaluronic acid, glucosamine, glucuronic acid, glycerol, urea, polyhydric alcohol, etc. The effect can be further enhanced.

EXAMPLES Next, although an Example demonstrates this invention in detail, this invention is not limited to these Examples. In addition, all content is mass%. In addition, the saffron extract used in the examples is obtained by immersing saffron powder obtained from Crocus sativus in 99% ethanol, filtering insoluble matters, and then removing ethanol (yield 18.9%). .

[Test Example 1: Evaluation of tension and flexibility improvement]
Emulsified cosmetics having the respective compositions shown in Table 1 were prepared by a conventional method. For 10 female subjects in their 40s and 60s, control was applied to one forearm and the cosmetics of each example and comparative example were applied to the other forearm twice a day for 2 weeks. It was. According to the evaluation criteria shown in Table 2, the panelists themselves evaluated the tension feeling and flexibility improvement degree of each Example / Comparative Example when compared to the tension feeling and flexibility improvement degree on the control coating side, and the total of all panelists The score was used as the evaluation result. Therefore, the higher the score, the better the sense of tension and flexibility for control. The results are shown in Table 3.

[Test Example 2: Evaluation of wrinkle improvement]
The emulsified cosmetic used in Test Example 1 was used. Apply 10 female subjects in their 40s to 60s as a group, apply the control to one corner of the eye and the cosmetics of any of the Examples and Comparative Examples to the other corner of the eye twice a day for one month. Went. According to the evaluation criteria shown in Table 2, the panel itself evaluates the degree of wrinkle improvement of each Example / Comparative Example when compared to the degree of wrinkle improvement on the control coating side, and the evaluation result with the total score of all panelists did. Therefore, it shows that it is excellent in the wrinkle improvement effect with respect to control, so that a score is high. The results are shown in Table 3.

[Test Example 3: Rough skin improvement evaluation]
The emulsified cosmetic used in Test Example 1 was used. For 10 panelists who feel rough skin on the outer side of the lower limbs, control the lower limbs of one foot and the emulsions of each Example and Comparative Example on the outer limbs of the other foot for 1 day. It was applied twice and used continuously for one week. According to the evaluation criteria shown in Table 2, the paneler himself evaluates the rough skin improvement degree of each Example / Comparative Example when compared to the rough skin improvement degree of the control application side, and the evaluation result with the total score of all the panelists did. Therefore, it shows that it is excellent in the rough skin improvement effect with respect to control, so that a score is high. The results are shown in Table 3.

From Table 1 and Table 3, Examples 1-3 which are the skin external preparation composition of this invention have a feeling of tension compared with the skin external preparation composition of Comparative Examples 1-4 which does not satisfy the structural requirements of this invention. -It turns out that it is excellent in the softness improvement effect, the wrinkle improvement effect, and the rough skin improvement effect.

Example 4
An emulsion having the composition shown below was prepared by a conventional method. When evaluated by the above test, it was confirmed that it was excellent in tension / flexibility improvement effect, wrinkle improvement effect, and rough skin improvement effect.

(mass%)
Ethanol 10.0
Polyoxyethylene hydrogenated castor oil (60 EO) 1.0
Glycerin 3.0
1,3-butylene glycol 2.0
Dipropylene glycol 3.0
Polyethylene glycol 1500 1.0
Polyoxyethylene (10) methyl glucoside 1.0
Sodium hydrogen phosphate 0.05
Potassium dihydrogen phosphate 0.05
Edetate disodium 0.05
Methylparaben 0.1
(R)-(−)-3-Methylcyclopentadecanone 0.0005
(S)-(+)-3-Methylcyclopentadecanone 0.0005
Saffron extract 0.001
N-methyl-L-serine 0.1
N-acetylglucosamine 1.0
Riboflavin 0.01
Ascorbic acid glucoside 0.1
Allantoin 0.1
Enmeso Extract 1.0
Purified water Remaining amount of 100

Example 5
An emulsion having the composition shown below was prepared by a conventional method. When evaluated by the above test, it was excellent in tension, flexibility improvement effect, wrinkle improvement effect, and rough skin improvement effect.

(mass%)
Stearic acid 1.0
Glyceryl monostearate 2.0
Cetanol 1.0
Cholesterol 0.5
Vaseline 2.0
Squalane 5.0
Liquid paraffin 5.0
Dimethylpolysiloxane 1.0
Butylparaben 0.1
Methylparaben 0.1
Sodium N-stearoyl glutamate 1.0
Polyethylene glycol 4000 1.0
Polyoxyethylene (20) methyl glucoside 2.0
Alkyl-modified carboxyvinyl polymer 0.2
Gellan gum 0.2
Glycerin 2.0
Dipropylene glycol 3.0
(R)-(−)-3-Methylcyclopentadecanone 0.001
Saffron extract 0.001
N-methyl-L-serine 0.1
N-acetylglucosamine 2.0
Shobu extract 1.0
Wild time extract 0.5
Aloe extract 1.0
Fennel extract 0.5
Purified water Remaining amount of 100

Example 6
A cream having the composition shown below was prepared by a conventional method. When evaluated by the above test, it was excellent in tension, flexibility improvement effect, wrinkle improvement effect, and rough skin improvement effect.

(mass%)
Stearic acid 2.0
Glyceryl monostearate 2.0
Cetanol 3.0
Cholesterol 0.5
Vaseline 2.0
Squalane 5.0
Liquid paraffin 10.0
Dimethylpolysiloxane 1.0
Butylparaben 0.1
Methylparaben 0.1
Sodium N-stearoyl glutamate 1.0
Polyethylene glycol 6000 1.0
Polyoxyethylene (20) methyl glucoside 1.0
Carboxyvinyl polymer 0.15
Alkyl-modified carboxyvinyl polymer 0.15
Alginic acid 0.1
Hyaluronic acid 0.05
Glycerin 5.0
Dipropylene glycol 3.0
Dipotassium glycyrrhizinate 0.1
Lactic acid bacteria culture solution 0.5
Yeast extract 1.0
(R)-(−)-3-Methylcyclopentadecanone 0.0005
(S)-(+)-3-Methylcyclopentadecanone 0.0005
Saffron extract 0.001
N-methyl-L-serine 0.1
N-acetylglucosamine 0.1
Retinol 0.5
Seaweed extract 1.0
Yokuinin extract 1.0
Purified water Remaining amount of 100

Claims (1)

(A) one or more dermal hyaluronic acid production promoters selected from 3-methylcyclopentadecanone, N-methyl-L-serine or a salt thereof; and (B) Crocus sativus. Contains one or more epidermal hyaluronic acid production promoters selected from the resulting extract or essential oil, N-acetylglucosamine, and from 3-methylcyclopentadecanone or Crocus sativus An external preparation composition for skin, comprising the obtained extract or essential oil as an essential component.