JP2022040765A - Stimulating sensation promoter of menthol - Google Patents

Abstract

To provide an irritating feeling promoter of menthol which not only simply promotes cool and refreshing feeling of menthol but also can impart refreshing use feeling demanded in a male cosmetic or the like to a menthol-containing product, and a method for promoting stimulating sensation of menthol by using the irritating feeling promoter.SOLUTION: A stimulating sensation promoter of menthol which consists of one or more selected from the group consisting of a component (A) menthyl methyl ether, and a component (B) N-(ethoxycarbonylmethyl)-3-p-menthane carboxamido and N-ethyl-p-menthane-3-carboxamide, and a composition for inducing stimulating sensation which contains the component (A), the component (B) and a component (C) menthol, and a mass ratio between the component (A), the component (B) and the component (C) is (A):(B):(C)=1:1:100 to 10:10:100.SELECTED DRAWING: None

Description

The present invention relates to a composition for enhancing the stimulating sensation of menthol used in cosmetics, pharmaceuticals, quasi-drugs, daily miscellaneous goods, etc., and a method for enhancing the stimulating sensation of menthol.

By blending a cooling sensation substance such as menthol into the product, it is possible to give a refreshing feeling and a refreshing feeling during and after the use of the product. Many body care, skin care, hair care products, etc. containing these cooling substances are commercially available. Especially in the summer, for men's body care and skin care products, products with a stronger refreshing sensation are preferred, so demand for products containing a cooling sensation substance is expanding. In such products, it is conceivable to increase the amount of menthol as a method of enhancing the refreshing sensation. However, simply increasing the amount of menthol causes a refreshing sensation as well as a stimulating sensation such as tingling pain, hot flashes, and itching sensation derived from menthol, which causes a problem that the usability is rather impaired.

Therefore, attempts have been made to enhance the refreshing sensation while suppressing the stimulating sensation of menthol. For example, by blending 2-methyl-3- (l-menthyloxy) propane-1,2-diol with a cooling sensation substance such as menthol, a refreshing and cool cooling sensation or a refreshing sensation is suppressed while suppressing irritation. Can be sustained or enhanced (Patent Document 1). In addition, among the cooling sensation substances, N-ethyl-p-menthane-3-carboxamide or trimethylisopropylbutaneamide is used in combination with a mentyl ester to suppress unnecessary roughness and flavor characteristics into a product. It can bring about a refreshing feeling that lasts for a long time (Patent Document 2). Further, as a skin external preparation having an excellent cooling sensation, there is a skin external preparation containing menthol, a compound having a menthol group and an OH group such as mentoxypropanediol, and a menthol ester such as menthol ester of pyrrolidone carboxylic acid. (Patent Document 3). These three types of cooling sensation substances have different cooling sensation peaks, and by combining these, the cooling sensation can be maintained. Further, a cooling sensation composition having a higher cooling sensation intensity and durability than the conventional cooling sensation composition has been proposed by using a specific cooling sensation substance such as L-menthol in combination with vanillyl butyl ether. (Patent Document 4).

By using the above-mentioned prior art, the irritation of menthol can be suppressed, the refreshing sensation can be enhanced and sustained, and a certain effect can be obtained in improving the usability of the menthol-containing product. However, simply enhancing and sustaining the refreshing sensation is not sufficient to obtain the refreshing feeling that is required especially for men's cosmetics, and technology for further enhancing the refreshing sensation is required. There is.

Japanese Unexamined Patent Publication No. 9-217083 Special Table 2009-591003 Japanese Unexamined Patent Publication No. 2014-201552 Japanese Patent No. 4017758

The present invention is not merely to enhance the refreshing sensation of menthol, but to provide a menthol-containing product with a refreshing feeling of use as required for men's cosmetics and the like, and a menthol stimulating sensation enhancer. It is an object of the present invention to provide a method for enhancing the stimulus sensation of menthol by using the stimulant sensation enhancer.

As a result of various studies on materials that can give a refreshing feeling to the menthol-containing product, the present inventors have found that menthylmethyl ether (MME) and N- (ethoxycarbonylmethyl) -3-, which are known as compounds having a cooling sensation effect. It has been found that when p-menthanecarboxyamide (WS-5) is used in combination with menthol, a refreshing skin sensation not found in conventional menthol-containing products is imparted. Surprisingly, this exhilaration is caused by the stimulus of menthol, which has been regarded as an object to be avoided, and the stimulus that lasts for a long time is perceived as an unfavorable sensation. It has been found that when the stimulus is strongly felt immediately after being applied to the skin and then rapidly reduced, it is perceived as a very preferable refreshing sensation in combination with the refreshing sensation of menthol. Furthermore, it was found that the same effect can be obtained when N-ethyl-p-menthane-3-carboxamide (WS-3) is used instead of N- (ethoxycarbonylmethyl) -3-p-menthancarboxyamide. , The present invention has been completed.

That is, the present invention is as follows.
[1] A menthol irritation enhancer, which comprises the following components (A) and (B).
(A) One or more selected from the group consisting of (A) mentholmethyl ether (B) N- (ethoxycarbonylmethyl) -3-p-menthancarboxyamide and N-ethyl-p-menthan-3-carboxamide [2] The stimulant sensation enhancer of menthol according to the above [1], wherein the mass ratio of the component (A) to the component (B) is (A) :( B) = 10: 1 to 1:10.
[3] The following components (A) to (C) are contained, and the mass ratio of the following component (A), the following component (B) and the following component (C) is (A) :( B) :( C) =. A composition for inducing a stimulating sensation, which is characterized by being 1: 1: 100 to 10:10: 100.
(A) Menthyl Methyl Ether (B) One or more selected from the group consisting of N- (ethoxycarbonylmethyl) -3-p-menthancarboxyamide and N-ethyl-p-mentane-3-carboxamide (C) Menthol [4] The stimulant-inducing composition according to the above [3], which is a fragrance composition.
[5] Menthol is contained so that the content of the whole product is 0.05 to 0.8% by mass, and the stimulant sensation enhancer of the menthol of the above [1] or [2] is contained. How to make the product.
[6] A method for producing a menthol-containing product, which comprises the composition for inducing a stimulating sensation according to the above [3] or [4].
[7] The method for producing a menthol-containing product according to [6], wherein the composition for inducing a stimulating sensation is contained so that the content of menthol in the entire product is 0.05 to 0.8% by mass.
[8] The method for producing a menthol-containing product according to any one of [5] to [7] above, wherein the menthol-containing product is a cosmetic, a pharmaceutical product, a quasi-drug, or a daily miscellaneous product.
[9] The following components (A) to (C) are contained, and the mass ratio of the following component (A), the following component (B) and the following component (C) is (A) :( B) :( C) =. A menthol-containing product having a content of 1: 1: 100 to 10:10: 100 and having the following component (C) in an amount of 0.05 to 0.8% by mass based on the entire product.
(A) Menthyl Methyl Ether (B) One or more selected from the group consisting of N- (ethoxycarbonylmethyl) -3-p-menthancarboxyamide and N-ethyl-p-menthan-3-carboxamide (C) Menthol [10] The method for producing a menthol-containing product according to [10], wherein the menthol-containing product is a cosmetic, a pharmaceutical, a non-medicinal product, or a daily miscellaneous product.
[11] A method for enhancing the stimulating sensation of a menthol-containing product, wherein 1 to 10 parts by mass of each of the following components (A) and (B) is blended with respect to 100 parts by mass of menthol.
(A) One or more selected from the group consisting of (A) mentholmethyl ether (B) N- (ethoxycarbonylmethyl) -3-p-menthancarboxyamide and N-ethyl-p-menthan-3-carboxamide [12] The method for enhancing the irritation feeling of the menthol-containing product according to the above [11], wherein the menthol-containing product is a cosmetic, a pharmaceutical product, a non-medicinal product, or a daily miscellaneous product.

When the menthol irritation enhancer according to the present invention is used in cosmetics or the like in combination with menthol, the irritation sensation of menthol can be enhanced and a refreshing skin sensation can be imparted in combination with the refreshing sensation of menthol. Since the irritation of menthol enhanced by the irritation enhancer is rapidly reduced, an extremely good usability can be obtained.

Hereinafter, the present invention will be described in detail according to an embodiment.

[1] Menthol irritation enhancer The menthol irritation enhancer according to the present invention comprises the following component (A) and the following component (B).
Component (A): Menthylmethyl Ether Component (B): One or more selected from the group consisting of N- (ethoxycarbonylmethyl) -3-p-menthancarboxyamide and N-ethyl-p-mentane-3-carboxamide.

The menthylmethyl ether of the component (A) is a compound represented by the following formula (1). Menthylmethyl ether is a known compound that has a cooling sensation effect and is used as a fragrance material for confectionery such as chewing gum and toothpaste, but when combined with the component (B), the stimulating feeling of menthol is enhanced. It was not known to show the effect of chewing gum.

Mentyl methyl ether is prepared by reacting, for example, a methylating agent such as menthol and dimethyl sulfate with a phase transfer catalyst under basic conditions, as described in Example 1 of JP-A-2004-513960. It can be synthesized by letting it.

The component (B) N- (ethoxycarbonylmethyl) -3-p-menthancarboxamide (WS-5) is a compound represented by the following formula (2), and is N-ethyl-p-menthane-3-. Carboxamide (WS-3) is a compound represented by the following formula (3). All of these are carboxamide derivatives of menthol. Both WS-5 and WS-3 are compounds known as cooling agents, and while they have a stronger cooling sensation than menthol, they have a milder odor and irritation than menthol, so they are suitable for chewing gum and toothpaste. It is used. However, it has not been known that when combined with the component (A), it has an effect of enhancing the stimulating sensation of menthol.

Both WS-5 and WS-3 can be purchased from Renessenz LLC, Fujifilm Wako Pure Chemical Industries, Ltd., Tokyo Chemical Industry Co., Ltd., Kanto Chemical Co., Ltd., etc.

Menthol is widely used in cosmetics, external skin preparations, etc. as a substance that imparts a refreshing sensation, but when the blending amount is increased, an unpleasant irritating sensation is felt. This irritation is generally perceived as an unpleasant sensation because it lasts for a while after the cosmetics or the like are applied to the skin. On the other hand, when the irritation enhancer according to the present invention is used in combination with menthol, the irritation immediately after the menthol comes into contact with the skin is felt more strongly, but the irritation enhanced by the irritation enhancer according to the present invention is felt. Is rapidly reduced, so that discomfort due to persistent irritation is suppressed. This, combined with the refreshing sensation of menthol and the enhanced stimulating sensation, makes it possible to feel a very favorable refreshing sensation. Therefore, the stimulant enhancer according to the present invention is suitable as an additive for menthol-containing products, and is particularly suitable as an additive for men's cosmetics and the like, which prefer a strong refreshing sensation.

The ratio (mass) of the component (A) and the component (B) in the menthol stimulus-enhancing agent according to the present invention is not particularly limited as long as the amount can obtain the stimulus-enhancing effect on menthol. As the menthol irritation enhancer according to the present invention, the content of the component (A) and the component (B) is component (A): component (B) = 10: 1 to 1:10 (mass ratio). Is preferable. When the stimulant sensation enhancer of menthol contains both WS-5 and WS-3 as the component (B), the content of the stimulant sensation enhancer component (B) is the same as the content of WS-5. It is the total content of WS-3.

By incorporating the menthol-containing product according to the present invention into a menthol-containing product, the menthol-induced irritation of the product can be further enhanced. The amount of the stimulus-enhancing agent contained in the menthol-containing product is not particularly limited as long as the stimulant-enhancing effect of the menthol is exhibited by the stimulant-enhancing agent. The menthol-containing product according to the present invention preferably contains 2 to 20 parts by mass with respect to 100 parts by mass of the menthol in the menthol-containing product. It is more preferable to let it.

The menthol-containing product containing the menthol irritation enhancer according to the present invention is not particularly limited as long as it is a product containing menthol, but it is preferably an external preparation that comes into direct contact with the skin. Examples of the external preparation that comes into direct contact with the skin include cosmetics, pharmaceuticals, quasi-drugs, daily miscellaneous goods, etc. that are directly applied to the skin.

Cosmetics include skin care cosmetics (cleansing foam, lotion, after-shaving lotion, etc.), hair cosmetics (hair tonic, hair cream, hair treatment, hair oil, hair liquid, set lotion, hair gel, hair spray, hair foam, hair dye). Agents, etc.), tanning cosmetics (suntan, sunscreen products), etc.

Pharmaceuticals include anti-inflammatory agents (anti-itch, etc.), and quasi-drugs include medicated cosmetics (antiperspirant deodorant, medicated soap, medicated shampoo, whitening / rough skin prevention cosmetics, etc.).

Daily miscellaneous goods include soap, hair care products (shampoo, conditioner, rinse-in shampoo, conditioner, treatment, hair pack, etc.), bath salts (bath salts, bath tablets, bath liquid, foam bath, bath oil, etc.), body shampoo. , Hand soap and the like.

The menthol content in the menthol-containing product containing the menthol irritation enhancer according to the present invention is not particularly limited, and can be appropriately determined in consideration of the product quality required for various products. Since the effect of the menthol irritation enhancer according to the present invention can be more fully exerted, the menthol content in the menthol-containing product containing the menthol irritation enhancer according to the present invention is 0.05 to 0. It is preferably in the range of 8.8% by mass, and more preferably in the range of 0.1 to 0.6% by mass. When the content of menthol in the entire product is within these ranges, a sufficient refreshing feeling due to menthol can be obtained while suppressing a prolonged stimulus feeling of menthol which is felt to be unpleasant.

The menthol irritation enhancer according to the present invention can be in various dosage forms. For example, it may be a water-soluble or oil-soluble liquid, a paste, or a powder. Various dosage forms can be produced by known methods.

[2] Method for enhancing the stimulus sensation of a menthol-containing product The menthol-containing product contains the component (A) and the component (B) as separate raw materials in place of the menthol stimulus enhancer according to the present invention. Also, the stimulating feeling of the menthol-containing product can be enhanced. The amount of the component (A) and the component (B) to be blended in the menthol-containing product is not particularly limited as long as the amount of both components exerting the stimulating effect of menthol. For example, it is preferable that the menthol-containing product contains 1 to 10 parts by mass of the component (A) and the component (B) with respect to 100 parts by mass of the menthol in the menthol-containing product.

The menthol-containing product containing the component (A) and the component (B) is not particularly limited as long as it is a product containing menthol, but it is preferably an external preparation that comes into direct contact with the skin. Examples of the external preparation that comes into direct contact with the skin include cosmetics, pharmaceuticals, quasi-drugs, daily miscellaneous goods, etc. that are directly applied to the skin. Examples of these cosmetics, pharmaceuticals, quasi-drugs, and daily miscellaneous goods include the same as described above.

[3] Composition for Inducing Stimulation The stimulant-enhancing agent for menthol according to the present invention can be mixed with menthol in advance to prepare a composition for inducing stimulus. When the mixture of the menthol irritation enhancer and menthol according to the present invention is brought into direct contact with the skin, a stronger irritation sensation can be evoked and a good refreshing sensation can be obtained as compared with the case of menthol alone. That is, the composition for inducing a stimulating sensation according to the present invention contains the following component (A), the following component (B), and the following component (C).
Component (A): Menthylmethyl Ether Component (B): One or more selected from the group consisting of N- (ethoxycarbonylmethyl) -3-p-menthancarboxyamide and N-ethyl-p-menthan-3-carboxamide. Ingredient (C): Menthol

The ratio (mass) of the component (A), the component (B), and the component (C) in the stimulus-inducing composition according to the present invention is such that the component (A) and the component (B) have an effect of enhancing the stimulus sensation on menthol. The amount may be as long as it can be used, and there is no particular limitation. In the composition for inducing a stimulating sensation according to the present invention, the content of the component (A) and the component (B) and the content of the component (C) are as follows: component (A): component (B): component (C) =. It is preferably 1: 1: 100 to 10:10: 100 (mass ratio), and component (A): component (B): component (C) = 5: 5: 100 to 10:10: 100 (mass ratio). ) Is more preferable. When the ratio of the component (A), the component (B), and the component (C) is within the above range, the stimulating composition or the product containing the stimulant feeling is unpleasant when directly contacted with the skin. Sufficient exhilaration due to menthol can be obtained while suppressing the prolonged stimulus of menthol.

The stimulus-inducing composition according to the present invention contains components other than the components (A) to (C) as long as the stimulus-inducing effect of the components (A) to (C) is not impaired. You may. Examples of the other components include water; organic solvents such as alcohol, glycerin and propylene glycol; excipients such as dextrin, shoe cloth, pectin and chitin; fats and oils; emulsifiers; antioxidants and the like. These components can be appropriately selected from, for example, additives generally used in fragrance compositions, and appropriately blended and used.

Menthol is a commonly used fragrance material. Therefore, the composition for inducing irritation according to the present invention can be used as a fragrance composition by itself. When the stimulating sensation evoking composition according to the present invention is a fragrance composition, the stimulating sensation evoking composition may further contain one or more kinds of fragrance materials, if necessary. Examples of the fragrance material include the fragrance raw materials (essential oils) described in "Patent Agency Gazette Well-known Conventional Technology Collection (Fragrance) Part III Perfume for Cosmetics" (issued on June 15, 2001, Japan Patent Office). , Essence, concrete, absolute, extract, oleoledin, resinoid, recovered flavor, carbon dioxide extracted essential oil, synthetic fragrance), various plant extracts, etc., each of which can be blended in an amount that does not impair the effects of the present invention. ..

Specific examples of fragrance ingredients include peppermint, corn mint, penny royal mint, spearmint, bergamot mint, peppermint, lavender, lavandin, rosemary, basil, sweet majorum, oregano, thyme, sage, geranium, winter green, and taragon. , Black currant, natural fragrances such as essential oils obtained from plants such as butu; menthol, menthol, isomenthon, mentylacetate, 2-sec-butylcyclohexanone, pregon, isopregol, isopregyl acetate, l-carboxylic, dihydrocarboxylic, l -Synthetic fragrances such as carveol, methylsalicylate, ethylsalicylate, cineole, carvone, timole, and estragor can be exemplified.

In addition, in the case where the composition for inducing a stimulating sensation according to the present invention further contains other components in the components (A) to (C), the other components contain menthol such as peppermint oil. When a natural fragrance material is contained, the content of menthol in the stimulating sensation-inducing composition according to the present invention includes the menthol contained in the natural fragrance material in the blended component (C). Means content.

A menthol-containing product can be produced by incorporating the stimulating composition according to the present invention into various products, particularly external preparations directly applied to the skin. Direct application of the menthol-containing product to the skin elicits an enhanced but rapidly disappearing irritant sensation. The product containing the stimulating composition according to the present invention is not particularly limited, but is preferably an external preparation that comes into direct contact with the skin. Examples of the external preparation that comes into direct contact with the skin include cosmetics, pharmaceuticals, quasi-drugs, daily miscellaneous goods, etc. that are directly applied to the skin. Examples of these cosmetics, pharmaceuticals, quasi-drugs, and daily miscellaneous goods include the same as described above.

The amount of the stimulating sensation-inducing composition according to the present invention contained in various products is not particularly limited as long as the stimulating sensation-inducing composition can elicit a stimulating sensation caused by menthol. The amount of the stimulating composition according to the present invention to be contained in the product is preferably such that the menthol content in the product is in the range of 0.05 to 0.8% by mass, and 0. It is more preferable that the amount is in the range of 1 to 0.6% by mass. When the content of menthol in the whole product is within these ranges, when the product is applied directly to the skin, the menthol feels unpleasant and the menthol is not irritated for a long time, and the menthol gives a sufficient refreshing feeling. can get.

The composition for inducing a stimulating sensation according to the present invention can be in various dosage forms. For example, it may be a water-soluble or oil-soluble liquid, a paste, or a powder. Various dosage forms can be produced by known methods.

The contents of the components (A) to (C) in the composition or the product can be calculated from the blending ratio of the raw materials. It can also be measured by gas chromatography-mass spectrometry (GC / MS method).

Hereinafter, the present invention will be specifically described with reference to Examples, but the present invention is not limited thereto. Further, unless otherwise specified, "%" means "mass%".

[Example 1, Comparative Examples 1 to 6]
A lotion containing menthol was prepared, and its cooling sensation and irritation were examined.

<Making lotion base>
Lotion bases were made with the compositions shown in Table 1. First, all the A phases were mixed, heated and dissolved at 80 ° C., cooled to 40 ° C., and the B phase components were sequentially added and stirred. The mixed and dissolved C phase was added to the obtained mixture and stirred. Then, the mixed and dissolved D phase was added to the obtained mixture and stirred. Finally, the mixed and dissolved E phase was added to the obtained mixture to adjust the pH to 6.5.

<Making lotion>
A base composition consisting of an activator (PEG-20 sorbitan cocoate), ethanol (EtOH) and lotion base (Lotion), in which menthol (MEN), menthylmethyl ether (MME), N- (ethoxycarbonylmethyl) -3-p- Mentan Carboxamide (WS-5), N-Ethyl-p-Menthol-3-Carboxamide (WS-3), Vanillyl Butyl Ether (VBE), and Vanillyl Ethyl Ether (VEE) are mixed in the composition shown in Table 2. To make a lotion. It has been reported that VBE and VEE enhance the intensity and sustainability of the cooling sensation of menthol when used in combination with menthol (Patent Document 4).

<Evaluation of coldness and irritation>
For each lotion produced, the feeling of coldness and irritation was evaluated. Specifically, a 100 μL sample (lotion) was dropped on the skin of the back of the subject's hand, and the sample was spread over the entire back of the hand. Immediately after application, 3 minutes, 5 minutes, 7 minutes, 10 minutes, 20 minutes, and 30 minutes after application, the subjects evaluated the feeling of coldness and irritation. The feeling of coldness and irritation was evaluated on a 5-point scale (1 is the weakest and 5 is the strongest) with the lotion of Criterion 1 as the standard (score value 3). The average value of the score values of the four subjects was used as the score value of each lotion. Table 3 shows the results of the sensory evaluation of the feeling of coldness, and Table 4 shows the results of the sensory evaluation of the feeling of stimulation.

Comparing the lotions of Criterion 1 and Comparative Example 5 and Comparative Example 6 in which the contents of menthol are different from each other, it was observed that both the feeling of coldness and the feeling of irritation tended to be stronger depending on the amount of menthol. Further, the lotion of Comparative Example 3 containing VBE had a slightly weaker feeling of coldness and irritation than the standard 1, and the lotion of Comparative Example 4 containing VEE had a slightly enhanced feeling of coldness but a feeling of irritation. It was weak, and no effect of enhancing the feeling of irritation was confirmed. In addition, the lotions of Comparative Example 2 containing only MME and Comparative Example 1 containing only WS-5 had a slightly enhanced cooling sensation immediately after application, but were about the same as the lotion of Standard 1 3 minutes after application. As for the feeling of irritation, no enhancing effect was confirmed with respect to Criterion 1. On the other hand, in Example 1 containing both MME and WS-5, both the cooling sensation and the stimulating sensation were confirmed to have an enhancing effect immediately after the application, but the cooling sensation was confirmed 5 minutes after the application. The feeling of irritation disappeared 3 minutes after application, but rather was weaker than that of Standard 1. From these results, by combining both MME and WS-5 with menthol, the feeling of coldness and irritation of menthol can be enhanced immediately after direct contact with the skin as compared with the case of menthol alone. Moreover, it was found that this enhancing effect disappears rapidly, and that the stimulating feeling enhancing effect that disappears rapidly makes the feeling of exhilaration excellent.

[Examples 2 to 3, Comparative Examples 7 to 8]
Lotions containing menthol, MME and WS-5 were prepared and the effect of the ratio of the contents of these three to the feeling of coldness and irritation was investigated. Specifically, first, a lotion was prepared in the same manner as in Example 1 except that the contents of menthol, MME and WS-5 were set to Table 5. The feeling of coldness and irritation of each of the obtained lotions was examined in the same manner as in Example 1. Table 6 shows the results of the sensory evaluation of the feeling of coldness, and Table 7 shows the results of the sensory evaluation of the feeling of stimulation. For reference, the lotion of Example 1 is also described. In addition, a summary of sensory evaluation is shown in Table 8.

The content ratio of the MME of the component (A), the WS-5 of the component (B), and the menthol of the component (C) is (A) :( B) :( C) = 1: 1: 100 to 10 :. In the lotions of Example 1, Example 2 and Example 3 which were 10: 100, the stimulating feeling was confirmed to have an enhancing effect immediately after application, but this enhancing effect disappeared 5 minutes after application. , A very good feeling of exhilaration was obtained. On the other hand, the lotion of Comparative Example 7 in which (A) :( B) :( C) = 0.1: 0.1: 100 did not have an enhancing effect on the stimulating sensation. Further, the lotion of Comparative Example 8 in which (A): (B): (C) = 50: 50: 100 was observed to have an enhancing effect of irritation immediately after application, but had an enhancing effect until 30 minutes after application. Was continuing.

[Examples 4 to 6, Comparative Examples 9 to 10]
Lotions containing menthol, MME and WS-5 were prepared and the effect of the ratio of menthol content to cooling and irritation was investigated. Specifically, first, a lotion was prepared in the same manner as in Example 1 except that the contents of menthol, MME, WS-5 or WS-3 were set to Table 9. The feeling of coldness and irritation of each of the obtained lotions was examined in the same manner as in Example 1. Table 10 shows the results of the sensory evaluation of the feeling of coldness, and Table 11 shows the results of the sensory evaluation of the feeling of stimulation. In addition, a summary of sensory evaluation is shown in Table 12.

In the lotions of Examples 4 and 5 in which the menthol content in the lotion was 0.05 to 0.8% by mass, both irritation and cooling sensation were enhanced from immediately after application to 3 to 5 minutes after application. The effect was confirmed, but after that, this enhancing effect disappeared, and a very good feeling of exhilaration was obtained. The lotion of Example 6 using WS-3 instead of WS-5 showed the same effect. On the other hand, in the lotion of Comparative Example 9 in which the menthol content in the lotion was 0.01% by mass, no enhancing effect was observed in both the stimulating sensation and the cooling sensation. In the lotion of Comparative Example 10 in which the menthol content in the lotion was 1% by mass, the enhancing effect was maintained from immediately after application to 30 minutes after application in both cold feeling and irritation, which was unpleasant irritation. I felt.

[Examples 7 to 8]
According to the formulation shown in Table 13, in a metal / glass / poly container containing 200 mL at room temperature, a vegetable deodorant, zinc paraphenolsulfonate, 1,3-butylene glycol, isopropyl myristate, (A) menthol methyl ether, (B) N- (ethoxycarbonylmethyl) -3-p-menthancarboxyamide or N-ethyl-p-menthan-3-carboxamide, and (C) menthol were dissolved in ethanol to prepare an antiperspirant stock solution. The same amount of LPG was mixed to prepare a cooling sensation antiperspirant (deodorant spray).

[Examples 9 to 10]
(1) Preparation of shampoo base According to the formulation in Table 14, the aqueous base is measured in a beaker, uniformly mixed while heating at 85 ° C., and then uniformly dissolved by adding an activator such as Na cocoyl glutamate while stirring. A shampoo base was prepared by adding 1% glutamic acid water and water.

(2) Preparation of Cooling Shampoo According to the formulation shown in Table 15, the oil-based base was measured in a beaker, and after uniform mixing, the shampoo base was added and uniformly mixed to prepare a cold feeling shampoo.

[Examples 11 to 12]
The cooling body soap of the present invention was prepared according to the formulation shown in Table 16.

Claims (12)

A menthol stimulant enhancer comprising the following components (A) and (B).
(A) Menthyl Methyl Ether (B) One or more selected from the group consisting of N- (ethoxycarbonylmethyl) -3-p-menthancarboxyamide and N-ethyl-p-mentane-3-carboxamide. The menthol irritation enhancer according to claim 1, wherein the mass ratio of the component (A) to the component (B) is (A) :( B) = 10: 1 to 1:10. It contains the following components (A) to (C), and the mass ratio of the following component (A), the following component (B), and the following component (C) is (A) :( B) :( C) = 1: 1. : 100 to 10:10:100, a composition for inducing a stimulating sensation.
(A) Menthyl Methyl Ether (B) One or more selected from the group consisting of N- (ethoxycarbonylmethyl) -3-p-menthancarboxyamide and N-ethyl-p-mentane-3-carboxamide (C) Menthol The stimulus-inducing composition according to claim 3, which is a fragrance composition. A method for producing a menthol-containing product, which comprises menthol so as to have a content of 0.05 to 0.8% by mass with respect to the entire product, and also contains the menthol irritation enhancer according to claim 1 or 2. .. A method for producing a menthol-containing product, which comprises the stimulating composition according to claim 3 or 4. The method for producing a menthol-containing product according to claim 6, wherein the stimulant-inducing composition is contained so that the content of menthol in the entire product is 0.05 to 0.8% by mass. The method for producing a menthol-containing product according to any one of claims 5 to 7, wherein the menthol-containing product is a cosmetic, a pharmaceutical product, a quasi-drug, or a daily miscellaneous product. It contains the following components (A) to (C), and the mass ratio of the following component (A), the following component (B), and the following component (C) is (A) :( B) :( C) = 1: 1. A menthol-containing product having a ratio of 100 to 10:10: 100 and a content of the following component (C) in the entire product of 0.05 to 0.8% by mass.
(A) Menthyl Methyl Ether (B) One or more selected from the group consisting of N- (ethoxycarbonylmethyl) -3-p-menthancarboxyamide and N-ethyl-p-mentane-3-carboxamide (C) Menthol The method for producing a menthol-containing product according to claim 9, wherein the menthol-containing product is a cosmetic, a pharmaceutical product, a quasi-drug, or a daily miscellaneous product. A method for enhancing the stimulating sensation of a menthol-containing product, wherein 1 to 10 parts by mass of each of the following components (A) and (B) is blended with 100 parts by mass of menthol.
(A) Menthyl Methyl Ether (B) One or more selected from the group consisting of N- (ethoxycarbonylmethyl) -3-p-menthancarboxyamide and N-ethyl-p-mentane-3-carboxamide. The method for enhancing the stimulus feeling of a menthol-containing product according to claim 11, wherein the menthol-containing product is a cosmetic, a pharmaceutical product, a quasi-drug, or a daily miscellaneous product.