JPH10147514A - Cosmetic - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a cosmetic capable of activating skin and scalp and excellent in skin-beautifying effect and hair-growing and hair-restoring effects by using a specific derivative of 10-hydroxy-2-decenoic acid which is an active ingredient of royal jelly. SOLUTION: This cosmetic comprises 10-hydroxy-2-decenoic acid of the formula (R is a monosaccharide residue, disaccharide residue or trisaccharide residue). Glucose, galactose, mannose, xylose, fructose, multitose, isomultitose, cellobiose, gentiobiose, etc., is preferably used as R in the formula. The content of glycocide of 10-hydroxy-2-decenoic acid of the formula is 0.001-10wt.%. The cosmetic is excellent in improvement in roughened skin and gloss of skin, stretch of wrinkles, contraction, etc., of slackness.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to cosmetics, and more particularly, to skin cosmetics which activate the skin and scalp and have excellent skin effects such as improvement of rough skin, improvement of skin luster, extension of wrinkles and convergence of tarmi. Another object of the present invention is to provide a hair cosmetic composition having excellent hair growth and hair growth effects.

[0002]

2. Description of the Related Art Conventionally, skin cosmetics and hair cosmetics have been blended with various animal and plant extracts or various compounds for the purpose of preventing rough skin, improving wrinkles, or growing and growing hair. For example, a placenta extract as an animal or plant extract,
Extracts such as royal jelly, yokunin, gougon, and bougainvillea, and examples of compounds include vitamin C, vitamin E, retinol derivatives, minoxidil, and the like.

[0003] Among them, royal jelly is excellent in safety and has been used not only as a nourishing tonic since ancient times, but also as an active ingredient in cosmetics and hair growth / hair restoration for the purpose of beautiful skin.

[0004]

However, since royal jelly is a complex mixture of lipids, proteins and saccharides, it has a very low solubility in water, ethanol or oil, and the protein component is thermally denatured during the production of cosmetics. For this reason, there are many restrictions on the blending amount and the dosage form because of the danger of occurrence of phenomena, and it is difficult to use them practically.

The inventors of the present invention have conducted studies to overcome the above-mentioned problems of royal jelly, and as a result, have found that the active ingredient of royal jelly is 10-hydroxy-2-decenoic acid. Application (JP-A-61-171413, JP-A-61-176510)
Reference).

However, it is also known that 10-hydroxy-2-decenoic acid is not only excellent in whitening effect, hair growth and hair growth effect as described in the above patent application, but also has actions such as antibacterial and blood flow increase. However, on the other hand, the solubility in the aqueous phase is extremely low, and there is still a problem in freely using it as an active ingredient of cosmetics.

The present invention has been made in view of the above-mentioned circumstances, and has been made to improve the restrictions on the use of 10-hydroxy-2-decenoic acid, activate the skin and scalp, and improve the roughness of the skin. It is an object of the present invention to provide a skin cosmetic excellent in beautiful skin effect such as improvement of skin gloss, extension of wrinkles, convergence of tarumi, and a hair cosmetic excellent in hair growth and hair growth effects.

[0008]

Means for Solving the Problems The present inventors have conducted intensive studies to solve the above-mentioned problems. As a result, when the hydroxyl group of 10-hydroxy-2-decenoic acid is converted into a glycoside, the solubility in the aqueous phase is reduced. In addition to improving glycerol, 10-hydroxy-2-decenoic acid that has been glycosidized has a more beautiful skin effect than 10-hydroxy-2-decenoic acid, and also has a hair growth and hair growth effect. The inventors have found that the present invention has been completed based on such findings.

That is, in the present invention, the total amount of the glycoside of 10-hydroxy-2-decenoic acid represented by the following general formula (I) is preferably 0.001 to 10% by weight based on the total amount of the cosmetic. The present invention relates to a cosmetic characterized by containing.

R—OCH ₂ (CH ₂ ) ₆ CH ＝ CHCOOH (I) (wherein, R represents a monosaccharide residue, a disaccharide residue or a trisaccharide residue.)

Hereinafter, the present invention will be described in detail.

10-hydroxy-2 applied to the present invention
The glycoside of -decenoic acid is a glycoside of the hydroxyl group of 10-hydroxy-2-decenoic acid as shown in the general formula (I), and specifically, for example, 10-glucosyl-
2-decenoic acid, 10-galactosyl-2-decenoic acid, 1
0-mannosyl-2-decenoic acid, 10-xylosyl-2
-Decenoic acid, 10-fructosyl-2-decenoic acid, 10
-Maltosyl-2-decenoic acid, 10-isomaltosyl-
2-decenoic acid, 10-cellobiosyl-2-decenoic acid, 1
0-gentiobiosyl-2-decenoic acid, 10-cordibiosyl-2-decenoic acid, 10-laminaribiosyl-2-
Decenoic acid, 10-nigerosyl-2-decenoic acid, 10-sambubiosyl-2-decenoic acid, 10-neoshesperidosyl-2-decenoic acid, 10-maltotriosyl-2-decenoic acid, 10-isomaltotriosyl -2-decenoic acid, 1
Examples thereof include 0-serotriosyl-2-decenoic acid and 10-gentiotriosyl-2-decenoic acid, and 10-glucosyl-2-decenoic acid from the viewpoints of a beautiful skin effect and a hair growth and hair growth effect.
Decenoic acid, 10-galactosyl-2-decenoic acid, 10-
Maltosyl-2-decenoic acid, 10-cellobiosyl-2-
Decenoic acid is preferred, especially 10-glucosyl-2-decenoic acid.

The 10-hydroxy-2 of the general formula (I)
Glycosides of -decenoic acid are obtained from 10-hydroxy-2-decenoic acid and acetylated sugars in Chiron, R .; Method (J.
Chem. Ecol. , 8: 709-713, 198.
It can be synthesized according to 2). At this time, a substance in which a sugar residue is bonded to a carboxyl group or a hydroxyl group of 10-hydroxy-2-decenoic acid, or both of them can be obtained. The target substance, 10-hydroxy-2-decene, is obtained by column purification or the like. Acid glycosides can be separated.
Hereinafter, the synthesis method will be described using 10-glucosyl-2-decenoic acid as an example.

[0014] 10-Hydroxy-2-decenoic acid and tetra-O-acetyl-D-glucopyranosyl bromide are mixed in dichloromethane under a mixed catalyst of tetramethylurea and silver triflate in a nitrogen stream while cooling with ice. And react for 2 hours. Thereafter, the dichloromethane layer was evaporated to dryness, the reaction product was fractionated and isolated by silica gel column chromatography, and then deacetylated using sodium methylate to obtain 10-glucosyl-2-decenoic acid.

Other glycoside compounds can also be produced according to the above method using the corresponding pyranosyl bromide derivative.

Next, in the cosmetic of the present invention, the content of the glycoside of 10-hydroxy-2-decenoic acid is preferably 0.001 to 10% by weight, more preferably the total amount, based on the total amount of the cosmetic. , 0.005 to 5% by weight. If it is less than 0.001% by weight, the beautiful skin effect and the hair growth / hair growth effect are reduced,
Use of an amount exceeding 10% by weight does not increase the effect and is uneconomical.

The 10-hydroxy-2 according to the present invention
-When blending the glucoside of decenoic acid in the cosmetic, there is no particular consideration, but it is preferable to dissolve the glucoside of 10-hydroxy-2-decenoic acid in a small amount of ethanol and then add the aqueous phase to the aqueous phase. Alternatively, a method of mixing with an oil phase component is preferable.

In the cosmetic of the present invention, in addition to the aforementioned active ingredients, various components generally used in cosmetics, that is, aqueous components, oil components, powder components, surfactants (emulsifiers), humectants, thickeners One or more components such as agents, coloring agents, fragrances, antioxidants, pH adjusters, chelating agents, preservatives, or ultraviolet protective agents, anti-inflammatory agents, and whitening agents can be blended.

Examples of the aqueous component include water (purified water),
Lower alcohols (ethanol, propanol, isopropanol) and the like.

Examples of the oily component include higher fatty acids (stearic acid, palmitic acid, myristic acid, lauric acid and esters thereof), higher alcohols (cetanol, lanolin alcohol, stearyl alcohol, cetostearyl alcohol, etc.) and the like. Waxes (solid paraffin, microcrystalline wax, ceresin wax, polyethylene wax, beeswax, wood wax, carnauba wax, candelilla wax, etc.), natural or synthetic oils (squalane, liquid paraffin, lanolin or derivatives thereof, olive oil, camellia oil, Cottonseed oil, oleyl alcohol, castor oil, petrolatum, diethoxyethyl adipate, silicone oil, fluorine oil, etc.)
Is mentioned.

Examples of the powder component include aluminum powder, titanium oxide powder, zinc oxide powder, iron oxide powder, acrylic powder, silica beads, talc, and sericite.

Examples of the surfactant include polyoxyethylene monooleate, polyoxyethylene cetyl ether, aluminum stearate, octyldodecanol, glycerin monostearate, propylene glycol monostearate and the like.

Examples of the humectant include glycerin, propylene glycol, 1,3-butylene glycol, dipropylene glycol, ethylene glycol, 1,4-butylene glycol, diglycerin, triglycerin, sorbit and its derivatives, and polyethylene glycol. Polyhydric alcohols include glucose, maltose, maltitol, sucrose, fructose, threitol, erythritol, sorbitol, starch-degrading sugar, hyaluronic acid, chondroitin sulfate, hydrolyzed collagen, carboxymethyl chitin and the like.

Examples of the thickener include carboxyvinyl polymer, CP jelly, carboxymethylcellulose,
Carrageenan, sodium alginate, polyvinyl acetate emulsion, polyvinyl alcohol, bentonite,
Vegum, synthetic hectorite and the like.

Examples of the antioxidant include dibutylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), sodium tocopherol-pyrosulfite, sodium bisulfate, tocopherol acetate, vitamin E, rosemary extract and the like. .

Examples of the pH adjuster include citric acid, lactic acid, tartaric acid, phosphoric acid and the like. Examples of the chelating agent include EDTA (ethylenediaminetetraacetic acid),
Thioglycolic acid, thiolactic acid, thioglycerin and the like.

As preservatives, for example, methyl, ethyl, propyl and butyl esters of p-oxybenzoic acid (referred to as methylparaben, ethylparaben, propylparaben and butylparaben, respectively), o-phenylphenol, dehydroacetic acid and Its salt, p-cresol,
m-cresol, o-chloro-m-xylenol and the like.

Examples of the ultraviolet protective agent include ascorbic acid or its derivative, isoferulic acid or its salt, oxybenzone or its derivative, p-aminobenzoic acid or its derivative, urocanic acid or its derivative, kojic acid, dibenzoylmethane or its derivative Derivatives, p-methoxycinnamic acid or derivatives thereof, fine particle titanium oxide, fine particle zinc oxide,
Fine particle iron oxide and the like.

Examples of the anti-inflammatory agent include glycyrrhetinic acid or a derivative thereof, glycyrrhizic acid or a derivative thereof, bisabolol, geraniin, malonier extract, and aloe extract.

As a whitening agent, for example, pantethein-S
-Sulfonic acid, isoferulic acid, ascorbic acid and its magnesium phosphate, arbutin, kojic acid, linoleic acid, tranexamic acid, esculin, vitamin A acid,
Retinol and the like.

Each of these components can be used alone or in combination of two or more.

The dosage form of the cosmetic of the present invention is not particularly limited, and those usually used for quasi-drugs, cosmetics, etc., for example, ointments, creams, emulsions, oils, lotions, packs, Examples include hair tonics, hair lotions, hair creams, hair treatments, shampoos, rinses, pomades, bath preparations, and the like, but from the viewpoint of transdermal absorption and stability, creams, emulsions, oils, and the like are particularly preferable. I can say.

[0033]

BEST MODE FOR CARRYING OUT THE INVENTION The action of the glycoside of 10-hydroxy-2-decenoic acid represented by the general formula (I) used in the present invention will be described below based on experimental examples. In addition, the glycoside of 10-hydroxy-2-decenoic acid used in Examples described later was obtained as described above.

[Evaluation test for human skin effect] (1) Samples Invention product 1: Skin cream of Example 1 described below Invention product 2: Emulsion of Example 2 described later Comparative product 1: In skin cream of Example 1 described below 10-
Skin cream in which glucosyl-2-decenoic acid is replaced with 10-hydroxy-2-decenoic acid Comparative product 2: 10- in the skin cream of Example 1 described later
Skin cream in which glucosyl-2-decenoic acid was replaced by vitamin C Comparative product 3: Emulsion in which 10-maltosyl-2-decenoic acid in the emulsion of Example 2 described below was replaced by 10-hydroxy-2-decenoic acid Article 4: an emulsion obtained by replacing 10-maltosyl-2-decenoic acid in the emulsion of Example 2 with vitamin E

(2) Test method Sixty girls aged 30 or older in Japan were randomly divided into three groups (groups A to C), each of which consisted of 20 women. The skin cream of the present invention product 1 was applied to the fingers of the group A, the skin cream of the comparative product 1 was applied to the fingers of the group B, and the skin cream of the comparative product 2 was applied to the fingers of the group C. On the other hand, the emulsion of the product 2 of the present invention was applied to the face of the group A, the emulsion of the comparative product 3 was applied to the face of the group B, and the emulsion of the comparative product 4 was applied to the face of the group C. The application was performed twice a day for 12 weeks, and an improvement in various evaluation factors after 12 weeks was compared between groups. The results are shown in Table 1 (skin cream) and Table 2 (emulsion).

[0036]

[Table 1]

[0037]

[Table 2]

As is evident from the results in Table 1, the skin cream of the present invention showed better results in all evaluation items than the comparative skin cream containing 10-hydroxy-2-decenoic acid or vitamin C. In particular, the improvement of fine wrinkles and gloss was more remarkable, and it was proved that the skin effect was excellent. Similarly, as is clear from the results in Table 2, the emulsion of the product of the present invention was also 10-hydroxy-
Compared to the emulsion of a comparative product containing 2-decenoic acid or vitamin E, a more remarkable improvement was observed, and it was proved that the skin beautiful effect was excellent.

[Human Hair Growth and Hair Growth Efficacy Evaluation Test] (1) Sample Product of the Invention 3: Hair tonic of Example 4 described below Product of the Invention 4: Hair tonic of Example 5 described below Product 5 of the invention: Example 6 described below Hair tonic comparative product 5: 10-
Hair tonic in which glucosyl-2-decenoic acid was replaced with 10-hydroxy-2-decenoic acid Control: 10-hydroxylated in the hair tonic of Example 4 described below.
Hair tonic in which the shortage is supplemented with water except for glucosyl-2-decenoic acid

(2) Test Method Fifty subjects complaining of Japanese hair thinning and alopecia were divided into five groups (D to H groups) of 10 subjects each. The group using the hair tonic of the product 4 of the present invention, the group F using the hair tonic of the product 5 of the present invention, the group G using the hair tonic of the comparative product 5, and the group H using the hair tonic of the control. A 24-week long-term continuous test was conducted. The application method was a method of evenly applying the composition to the head twice a day as in the usual tonic usage. The evaluation was performed on the 12th week and the 24th week, and the number of test subjects who felt that the amount of downy hair and hard hair had increased was measured. Furthermore, at the end of the application test, the condition of the scalp was improved,
Subjects also reported a reduction in the occurrence of dandruff. The results are shown in Tables 3 and 4.

[0041]

[Table 3]

[0042]

[Table 4]

As is evident from the results in Table 3, the hair tonic of the product of the present invention increased the number of people who had downy hair or hard hair at the same concentration as compared with the hair tonic of the comparative product, and showed a greater hair growth effect. It was proved to have Further, as shown in the results of Table 4, in all of the products of the present invention, the condition of the scalp at the end of the application test was improved, and there was a person who reported that the occurrence of dandruff was reduced. It was also revealed that the hair had a hair-growth effect. In addition, no skin damage such as deterioration of the scalp condition or inflammatory reaction was observed in any of the subjects during the long-term application test, and thus it was confirmed that there was no problem in safety.

[0044]

Embodiments of the present invention will be described below. The amounts in the examples are parts by weight.

Embodiment 1 Skin cream (A) Beeswax 3.0 Cetanol 2.0 Stearic acid 1.0 Vaseline 5.0 Olive oil 4.0 Squalane 5.0 Glycerin monostearate 1.0 POE (20) Sorbitan monostearate 3.0 10- Glucosyl-2-decenoic acid 0.5 (B) Glycerin 5.0 Polyethylene glycol 3.0 Preservative 0.3 Purified water 67.1 (C) Fragrance 0.1

<Preparation method>
Heat and mix at 0 ° C. Combine each component of (B), 70 ° C
The mixture is heated and mixed with the mixture, and the formulation (A) is added thereto and emulsified.
Cool to ° C. Further, (C) is added, and the mixture is cooled to room temperature with stirring.

Embodiment 2 Emulsion (A) Vaseline 1.0 Beeswax 1.0 Squalane 5.0 Sorbitan monostearate 1.0 POE (20) Monostearate 2.0 10-Maltosyl-2-decenoic acid 5.0 (B) Carboxyvinyl Polymer 0.2 Triethanolamine 0.5 Polyethylene glycol 4.0 Preservative 0.3 Purified water 79.9 (C) Fragrance 0.1

<Preparation method> The preparation was carried out in the same manner as in Example 1.

Embodiment 3 FIG. Lotion (A) POE (20) sorbitan monolaurate 1.5 POE (20) lauryl ester 0.5 ethanol 10.0 γ-tocopherol 0.02 10-galactosyl-2-decenoic acid 0.05 (B) glycerin 5.0 Propylene glycol 4.0 Citric acid 0.15 Sodium citrate 0.1 Purified water 78.68

<Preparation method> The components of (A) are combined and dissolved at room temperature. On the other hand, each component of (B) is also dissolved at room temperature, and is added to the component of (A) to be solubilized.

Embodiment 4 FIG. Hair tonic (A) 10-glucosyl-2-decenoic acid 5.0 1-menthol 0.2 ethanol 32.5 (B) Polyoxyethylene hydrogenated castor oil 0.5 Purified water 61.7 (C) Fragrance 0.1

<Preparation Method> Each of the components (A) and (B) was dissolved and mixed, and then (C) was added and mixed.

Embodiment 5 FIG. Hair tonic (A) 10-glucosyl-2-decenoic acid 0.05 l-menthol 0.2 ethanol 32.5 (B) Polyoxyethylene hydrogenated castor oil 0.5 Purified water 66.65 (C) Fragrance 0.1

<Preparation method> The preparation was carried out in the same manner as in Example 4.

Embodiment 6 FIG. Hair tonic (A) 10-glucosyl-2-decenoic acid 0.005 1-menthol 0.2 ethanol 32.5 (B) Polyoxyethylene hydrogenated castor oil 0.5 Purified water 66.6995 (C) Fragrance 0.1

<Preparation method> The preparation was carried out in the same manner as in Example 4.

Embodiment 7 Hair tonic (A) Menthol 0.2 Vitamin E 0.05 Carpronium chloride 0.1 Ethanol 50.0 10-Maltosyl-2-decenoic acid 0.05 (B) Propylene glycol 5.0 Vitamin B2 0.5 Yeast extract (Containing nucleic acid) 0.5 dipotassium glycyrrhizin 0.3 diphenhydramine hydrochloride 0.3 methyl paraben 0.2 purified water 42.7 (C) flavor 0.1

<Preparation method> The preparation was carried out in the same manner as in Example 4.

Embodiment 8 FIG. Hair treatment (A) Liquid paraffin 2.0 Methyl polysiloxane (10 cs) 2.0 Cetanol 4.0 10-Cellobiosyl-2-decenoic acid 5.0 (B) Stearyltrimethylammonium chloride 3.0 Distearyldimethylammonium chloride 0 5.5 Propylene glycol 5.0 Pyrocton olamine 0.25 Purified water 40.0 (C) Hydrolyzed collagen 0.5 Hyaluronic acid 0.01 Bovine placenta extract 0.5 Diphenhydramine chloride 0.25 Methyl paraben 0.2 Purification Water 36.69 (D) Fragrance 0.1

<Preparation method> After each of (A) and (B) was heated to 80 ° C, the two were mixed and emulsified.
After cooling to the vicinity, (C) and (D) were added and mixed.

Embodiment 9 Hair Shampoo (A) Triethanolamine Lauryl Sulfate 10.0 Sodium Lauryl Sulfate 5.0 Coconut Oil Diethanolamide 2.0 Propylene Glycol 5.0 Pyroctone Olamine 0.25 Benzyl Nicotinate 0.1 10-Galactosyl-2- Decenoic acid 5.0 (B) Trichlorocarbanilide 0.25 Purified water 72.3 (C) Fragrance 0.1

<Preparation Method> (A) was mixed at 80 ° C.
Thereafter, the mixture was cooled to around 40 ° C., and (B) and (C) were added and mixed.

The hair growth and hair growth effects of the cosmetics of the present invention obtained in Examples 7 to 9 were examined in the same manner as in Examples 4 to 6 or by a method similar thereto, and all of them showed excellent effects. . In addition, no skin disorders such as deterioration of the scalp condition and inflammatory reaction were observed at all.

[0064]

According to the present invention, as compared with the conventionally known cosmetics, not only the effect of improving the skin condition such as fine wrinkles, tarmi, lack of luster, and rough skin, but also the effect of hair growth and hair growth is achieved. And it can be used safely without any adverse effects on the skin.

Claims (3)

[Claims] 1. A cosmetic comprising a glycoside of 10-hydroxy-2-decenoic acid represented by the following general formula (I). _{R-OCH 2 (CH 2)} 6 CH = CHCOOH (I) ( wherein, R represents a monosaccharide, disaccharide residue or trisaccharide residue.) 2. The method according to claim 1, wherein the saccharide residue represented by R in the general formula (I) is glucose, galactose, mannose, xylose, fructose, maltose, isomaltose, cellobiose, gentiobiose, kojibiose, laminariviose, nigerose, sambuobiose. 2. The cosmetic according to claim 1, wherein the cosmetic is one selected from the group consisting of, neohesperidose, maltotriose, isomalttriose, cellotriose and gentiotriose. 3. The total content of the glycoside of 10-hydroxy-2-decenoic acid is 0.001 to 1 with respect to the total amount of the cosmetic.
The cosmetic according to claim 1, which is 0% by weight.