JP7245609B2 - external composition - Google Patents

Description

TECHNICAL FIELD The present invention relates to a composition for external use with improved cooling sensation persistence.

Menthol has a refreshing flavor peculiar to mint and is used in oral compositions such as dentifrices, mouth fresheners and mouthwashes. In addition, menthol is also used in cosmetic compositions because it gives a cool sensation (cold sensation) and gives a refreshing feeling when used. Thus, menthol is known as an extremely useful sensory stimulation substance.

Since menthol is an oil-soluble component, it is known that its solubility in water-based formulations increases when it is used in combination with ethanol. As the solubility in water-based preparations increases, so does the cooling sensation effect, so the combination system of menthol and ethanol is applied to many water-based preparations.

Furthermore, in addition to the combined use with ethanol, various formulations that improve the persistence of the cooling sensation brought about by menthol are being investigated. For example, Patent Literature 1 discloses that 2-methyl-3-(l-menthyloxy)propane-1,2-diol is used in combination with menthol and ethanol in an oral composition or the like to maintain a refreshing sensation. has been reported to be enhanced. Further, Patent Document 2 discloses that an external composition for skin using a combination of menthol, a compound having a menthyl group and an OH group (menthoxypropanediol), and menthyl pyrrolidone carboxylate has excellent persistence of cool feeling. Are listed.

JP-A-09-217083 JP 2014-201552 A

A composition containing menthol and a component that enhances cooling sensation persistence tends to have a higher cooling sensation and its persistence as the content of menthol increases. On the other hand, when the menthol content is high, excessive skin irritation due to menthol and component odor of menthol itself may be avoided. For this reason, there is a demand for a formulation that effectively improves the longevity of the cool sensation even when the menthol content is small.

An object of the present invention is to provide a pharmaceutical formulation that efficiently improves the longevity of cool feeling of a composition for external use containing menthol.

As a result of intensive studies, the present inventors have found that the coexistence of monomenthyl succinate in a menthol-containing composition for external use can efficiently improve the longevity of the cooling sensation. Furthermore, the present inventors have also found that by coexisting an amphipathic ester together with menthol and monomenthyl succinate, it is possible to enhance the sustained cooling sensation intensity, even though the amphiphilic ester itself does not have the cooling sensation intensity. The present invention has been completed through further studies based on these findings.

That is, the present invention provides inventions in the following aspects.
Section 1. An external composition comprising (A) menthol and (B) monomenthyl succinate.
Section 2. Item 2. The composition for external use according to Item 1, wherein the content of component (A) is 0.001 to 0.3% by weight.
Item 3. Item 3. The topical composition according to item 1 or 2, wherein the content of component (B) is 0.001 to 0.02% by weight.
Section 4. Item 4. The composition for external use according to any one of Items 1 to 3, further comprising (C) an amphipathic ester.
Item 5. Item 5. The composition for external use according to Item 4, wherein the component (C) is selected from the group consisting of dicarboxylic acid bis(polyoxyalkylene alkyl ether) esters and (eicosanedioic acid/tetradecanedioic acid) polyglyceryl-10.
Item 6. Item 6. The composition for external use according to Item 5, wherein the dicarboxylic acid bis(polyoxyalkylene alkyl ether) ester is cyclohexane-1,4-dicarboxylic acid bisethoxydiglycol.
Item 7. Item 7. The composition for external use according to any one of items 4 to 6, wherein the content of component (C) per 1 part by weight of component (A) is 80 to 600 parts by weight.
Item 8. Item 8. The composition for external use according to any one of Items 1 to 7, which is used after being applied to the skin and then washed off.
Item 9. (A) A method for improving the cooling sensation persistence in an external composition containing menthol, comprising:
A method for improving longevity of cool sensation, comprising blending (B) monomenthyl succinate together with the component (A) in an external composition.
Item 10. Item 10. The method for improving persistence of cold feeling according to Item 9, wherein (C) an amphiphilic ester is further blended together with the (A) component and the (B) component.

According to the present invention, it is possible to provide a pharmaceutical formulation that efficiently improves the longevity of cool sensation of an external composition containing menthol. can be improved.

1. Composition for external use The composition for external use of the present invention comprises (A) menthol (hereinafter sometimes referred to as component (A)) and (B) monomenthyl succinate (hereinafter sometimes referred to as component (B)). It is characterized by containing and. The composition for external use of the present invention is described in detail below.

(A) Menthol The topical composition of the present invention contains menthol as component (A). Menthol is a component known as a cooling agent that produces a cooling sensation.

Menthol may be any of d-, l-, and dl-forms, preferably l-form and dl-form, and more preferably l-form. Moreover, you may use the essential oil containing menthol as menthol.

The content of the component (A) in the composition for external use of the present invention is not particularly limited, and may be appropriately determined according to the cooling sensation to be imparted and the persistence of the cooling sensation. From the viewpoint of suppressing excessive skin irritation due to menthol and suppressing the component odor of menthol itself, the amount is preferably 0.001 to 0.3% by weight. Since the composition for external use of the present invention can efficiently improve the persistence of the cooling sensation, it is possible to effectively improve the persistence of the cooling sensation even when the content of the component (A) is small. can. From the same point of view, the content of component (A) in the composition for external use of the present invention is more preferably 0.001 to 0.05% by weight, more preferably 0.001 to 0.03% by weight. 0.001 to 0.02% by weight is preferred.

In addition, content of the (A) component shown here is the value converted into the amount of menthol, when using the essential oil containing menthol as (A) component.

(B) Monomenthyl succinate The composition for external use of the present invention contains monomenthyl succinate as the component (B). Component (B) by itself does not exhibit a cooling sensation intensity that exceeds that of component (A) at the same concentration. In particular, if it is 0.003% by weight or less, it does not exhibit even the cooling sensation intensity to the extent that it makes you feel a cold sensation. On the other hand, even if the concentration of component (B) alone exerts some degree of cooling sensation intensity, the cooling sensation does not last longer than component (A) at the same concentration. However, the composition for external use of the present invention can efficiently improve the cooling sensation persistence by combining the component (A) with the component (B).

Monomenthyl succinate is an ester of succinic acid and menthol, and the menthol may be any of d-, l-, and dl-forms, preferably l- and dl-forms, and more preferably. includes the l form.

The component (B) is a kind of organic acid ester of menthol. Some of the organic acid esters of menthol generate offensive odor when stored in a high-temperature environment. By combining with component (A) in an amount of 0.05% by weight or less, the off-flavour caused by storage in a high-temperature environment may become stronger. However, the component (B) itself has good storage stability in high temperature environments, and the storage stability in combination with component (A) is also excellent in high temperature environments.

The content of the component (B) in the composition for external use of the present invention is not particularly limited because it may be appropriately determined according to the persistence of the cooling sensation to be imparted, but is, for example, 0.001 to 0.02% by weight. , preferably 0.001 to 0.01% by weight, more preferably 0.001 to 0.005% by weight.

In the composition for external use of the present invention, the ratio of the components (A) and (B) is determined by the content of each component described above. The content of component (B) per 1 part by weight is preferably 0.05 to 1.5 parts by weight, more preferably 0.05 to 1 part by weight.

(C) Amphiphilic Ester The topical composition of the present invention contains an amphiphilic ester as component (C). Component (C) alone does not exert a strong cooling sensation, but in the composition for external use of the present invention, by combining components (A) and (B) with component (C), a lasting cooling sensation is enhanced. can be made Furthermore, the effect of enhancing the strength of the lasting cool sensation by combining the component (C) is exhibited not only when the composition for external use of the present invention is applied to the skin, but also when it is washed off.

In the present invention, the amphiphilic ester dissolves in ion-exchanged water adjusted to a conductivity of 70 to 110 μs / m at room temperature by 2% by mass or more as measured by the method specified in the Japanese Pharmacopoeia General Test Methods, and , 10% by mass or more at normal temperature (25° C.) of isotridecyl isononanoate (manufactured by Nisshin Oillio Group, Salacos 913), which is an oil agent, and ester surfactants are excluded.

The amphipathic ester is not particularly limited, but from the viewpoint of further improving the effect of enhancing the strength of the cooling sensation, dicarboxylic acid bis (polyoxyalkylene alkyl ether) ester and (eicosanedioic acid / tetradecanedioic acid) polyglyceryl-10 It is preferably selected from the group consisting of As the amphipathic ester, either dicarboxylic acid bis(polyoxyalkylene alkyl ether) ester or (eicosanedioic acid/tetradecanedioic acid) polyglyceryl-10 may be used alone, or both may be used in combination. may be used. Among these amphipathic esters, dicarboxylic acid bis(polyoxyalkylene alkyl ether) esters are more preferable from the viewpoint of further improving the effect of enhancing the strength of the sustained cooling sensation.

The dicarboxylic acid bis(polyoxyalkylene alkyl ether) ester used in the present invention is a diester compound of dicarboxylic acid and polyoxyalkylene alkyl ether. Specific examples of the dicarboxylic acid constituting the diester compound of dicarboxylic acid bis(polyoxyalkylene alkyl ether) ester include, for example, oxalic acid, malonic acid, succinic acid, tartaric acid, malic acid, glutaric acid, adipic acid, pemelic acid, suberic acid, azelaic acid, sebacic acid, aspartic acid, glutamic acid, acetonedicarboxylic acid, phthalic acid, cyclohexane-1,4-dicarboxylic acid and the like. Examples of the polyoxyalkylene alkyl ether constituting the diester compound include polyoxyethylene monoalkyl ether, more specifically, diethylene glycol monoethyl ether, triethylene glycol monoethyl ether, and the like. be done.

Among these dicarboxylic acid bis(polyoxyalkylene alkyl ether) esters, a diester compound of cyclohexane-1,4-dicarboxylic acid and diethylene glycol monoethyl ether is preferable from the viewpoint of further improving the effect of enhancing the strength of the continuous cooling sensation. Specifically, the INCI name (International Cosmetic Ingredient Dictionary and Handbook, 13th Edition, Vol. 1, CTFA, 2010, p.331): BIS-ETHOXYDIGLYCOL CYCLOHEXANE 1,4-DICARBOXYLATE, cycloto A compound called xane-1,4-dicarboxylic acid bisethoxydiglycol, and a diester compound of succinic acid and diethylene glycol monoethyl ether, specifically, INCI name (International Cosmetic Ingredient Dictionary and Handbook, 13th edition, Vol. 1, CTFA, 2010, p.331-332): BIS-ETHOXYDIGLYCOL SUCCINATE, compounds called bisethoxydiglycol succinate, more preferably cyclohexane-1, Bisethoxydiglycol 4-dicarboxylic acid can be mentioned.

Further, in the present invention, specific examples of the cyclohexane-1,4-dicarboxylic acid bisethoxydiglycol include "Neosolue-Aqulio (trade name)" manufactured by Nippon Fine Chemical Co., Ltd., and the like. Specific examples of the bisethoxydiglycol succinate include "High Aquostar DCS (trade name)" manufactured by KOKYU ALCOHOL KOGYO CO., LTD.

These dicarboxylic acid bis(polyoxyalkylene alkyl ether) esters may be used singly or in combination of two or more.

The (eicosanedioic acid/tetradecanedioic acid) polyglyceryl-10 used in the present invention is not particularly limited. product name)” and the like.

The content of the component (C) in the composition for external use of the present invention is not particularly limited because it may be appropriately determined according to the effect of enhancing the intensity of the sustained cooling sensation to be imparted, but for example, 0.2 to 5% by weight. , preferably 0.2 to 3% by weight, more preferably 0.5 to 2% by weight. In addition, as the content of the component (C) increases, the cooling sensation that lasts can be enhanced. From such a viewpoint, the content of component (C) is more preferably 0.8 to 2% by weight, more preferably 1.3 to 2% by weight, and particularly preferably 1.8 to 2% by weight. be done.

In the composition for external use of the present invention, the ratio of the components (A) and (C) is determined by the content of each component described above. The content of component (C) per 1 part by weight is preferably 80 to 600 parts by weight, more preferably 100 to 400 parts by weight, still more preferably 180 to 400 parts by weight, still more preferably 280 to 400 parts by weight, especially 380 to 400 parts by weight are preferred.

Although component (C) alone does not exhibit a cleansing action, when the composition for external use of the present invention contains a surfactant as a skin cleansing composition, coexistence with the surfactant cleanses the skin cleansing composition. can improve power. In particular, when the content of the surfactant is as low as 0.025 to 2% by weight, the skin cleansing composition can improve detergency while being hypoallergenic.

Other Ingredients The composition for external use of the present invention may contain, in addition to the above-mentioned ingredients, other bases and additives required for formulation, etc., to the extent that the effects of the present invention are not impaired. . Such additives are not particularly limited as long as they are pharmaceutically acceptable. 1,3-butylene glycol (1,3-BG), propylene glycol, isoprene glycol, diethylene glycol, dipropylene glycol, polypropylene glycol, glycerin, etc.); cationic surfactants, anionic surfactants, Surfactants such as amphoteric surfactants; preservatives (methylparaben, propylparaben, benzoic acid, sodium benzoate, sorbic acid, etc.), flavoring agents (citral, 1,8-cioneal, citronellal, farnesol, etc.), Coloring agents (tar pigments (Brown No. 201, Blue No. 201, Yellow No. 4, Yellow No. 403, etc.), cocoa pigments, chlorophyll, aluminum oxide, etc.), thickeners (carboxyvinyl polymer, hypromellose, polyvinylpyrrolidone, sodium alginate, Ethyl cellulose, sodium carboxymethyl cellulose, xanthan gum, carrageenan, etc.), pH adjuster (phosphoric acid, hydrochloric acid, citric acid, sodium citrate, succinic acid, tartaric acid, sodium hydroxide, potassium hydroxide, triethanolamine, triisopropanolamine, etc.) , Wetting agents (sodium dl-pyrrolidonecarboxylate solution, D-sorbitol solution, macrogol, etc.), stabilizers (dibutylhydroxytoluene, butylhydroxyanisole, sodium edetate, sodium metaphosphate, L-arginine, L-aspartic acid , DL-alanine, glycine, sodium erythorbate, propyl gallate, sodium sulfite, sulfur dioxide, chlorogenic acid, catechin, rosemary extract, etc.), antioxidants, UV absorbers, chelating agents, adhesives, buffers, Additives such as dissolution aids, solubilizers, and preservatives are included. These base materials and additives may be used singly or in combination of two or more. The contents of these base materials and additives can be appropriately set according to the dosage form and the like.

The composition for external use of the present invention may optionally contain other pharmacological components in addition to the above-described components within a range that does not impair the effects of the present invention. Examples of such pharmacological components include vitamins (vitamin A, vitamin B1, vitamin B2, vitamin B5, vitamin B6, vitamin B12, vitamin C, vitamin D, vitamin K, niacin, folic acid, biotin, lycopene, etc.), antihistamines (diphenhydramine, diphenhydramine hydrochloride, etc.), local anesthetics (procaine, tetracaine, bupipacine, mepipacaine, chloroprocaine, proparacaine, meprilcaine or salts thereof, orthocaine, oxethazaine, oxypolyentoxy Decane, Rohto extract, percamimpase, tecit decithin, etc.), anti-inflammatory agents (indomethacin, felbinac, diclofenac sodium, loxoprofen sodium, etc.), skin protective agents (collodion, castor oil, etc.), blood circulation-promoting ingredients (nonylic acid vanillylamide, benzyl nicotinate) , capsaicin, red pepper extract, etc.), cooling agents (camphor, borneol, etc.), mucopolysaccharides (sodium chondroitin sulfate, glucosamine, etc.), and the like. These pharmacological ingredients may be used singly or in combination of two or more. When these pharmacological ingredients are contained, the content thereof may be appropriately set according to the type of the pharmacological ingredient to be used, the expected effect, and the like.

Form The form of the composition for external use of the present invention is not particularly limited. preparations, gels, solid preparations, patches and the like, and among these, liquid preparations are preferred. Moreover, the composition for external use of the present invention may be in the form of impregnating a sheet substrate such as cotton or non-woven fabric with the composition for external use, which is a liquid agent.

Container The container for containing the composition for external use of the present invention is not particularly limited, and may be appropriately selected according to the form and application. , pump-type containers, tube-type containers, packaging bags, box-shaped containers, and the like. In particular, when the composition for external use of the present invention is in liquid form, the container includes a spray type container, pouring or dropping type container (especially washing bottle), pump type container, and pump foamer container. When the composition for external use of the present invention is impregnated into a sheet substrate, examples of the container include packaging bags and box-like containers.

Uses The composition for external use of the present invention is not particularly limited as long as it is applied to the skin rather than food. Skin cleansers used to remove makeup, cleansers used to remove makeup, and the like. Since the composition for external use of the present invention is excellent in lasting cooling sensation, it is particularly suitable for usage modes in which the composition for external use is in contact with the skin for a short period of time. Examples of the mode of use in which the skin is in contact with the skin for a short period of time include the mode of use that is rinsed off after being applied to the skin, more specifically, the above-described skin cleanser and cleansing.

Production method The skin cleanser composition of the present invention is prepared by mixing the aforementioned components (A) and (B), optionally blended (C) component, and optionally blended other components. It is produced by preparing the product into a predetermined form.

2. Method for Improving Cool Sensation Durability As described above, monomenthyl succinate can improve the cool sensation persistence in external compositions containing menthol. The present invention further provides a method for improving longevity of cool sensation, comprising adding monomenthyl succinate as component (B) together with component (A) to an external composition containing menthol as component (A). Furthermore, as described above, when an amphipathic ester is further added to an external composition containing menthol and monomenthyl succinate, it is possible to enhance the strength of the lasting cooling sensation. Therefore, in the method for improving the persistence of cool feeling of the present invention, it is preferable to blend an amphipathic ester as the component (C) together with the components (A) and (B).

In the present invention, "improving the duration of the cooling sensation" means that the cooling sensation lasts longer than when the concentration of the component (A) is the same and the component (B) is not contained. Enhancing the intensity of the lasting cooling sensation means that the intensity of the cooling sensation after a predetermined time has passed after application to the skin is greater than when the concentrations of the components (A) and (B) are the same and the component (C) is not included. Say things.

In the method for improving the persistence of cool sensation, the types and amounts of components used, the form of the composition for external use, etc. are as shown in the above column "1. Composition for external use."

EXAMPLES The present invention will be described in more detail with reference to examples below, but the present invention is not limited to these.

[Test Example 1]
A topical composition having the composition shown in Tables 1 to 3 was prepared. In Tables 1-3, menthol is l-menthol, mono-menthyl succinate is mono-l-menthyl succinate, menthyl lactate is l-menthyl lactate, and menthyl acetate is l-menthyl acetate. The prepared composition for external use was subjected to the following tests.

<Cooling intensity test (evaluation by leave-on)>
5 μl of the composition for external use was applied to each inner side of the forearm of 10 panelists and lightly spread. The panelists' self-reported strength of cooling sensation immediately after application was scored based on the following criteria.
3 points: feel a strong cold sensation
2 points: feeling cold
1 point: feel a slight cold sensation
0 points: No cold feeling at all

The scores of 10 panelists were averaged, and the average values were classified according to the following criteria to evaluate the degree of cold sensation intensity. The results are shown in Tables 1-3.
◎: Score average value is 2.5 or more and 3 or less
○: score average value of 1.5 or more and less than 2.5
△: score average value of 0.5 or more and less than 1.5
×: score average value of 0 or more and less than 0.5

<Cool sensation durability test (evaluation by leave-on)>
In the above cold sensation intensity test, after 5 μl of the external composition was applied to the inner side of the forearm of 10 panelists, 10 minutes, 20 minutes, 30 minutes, 40 minutes, 50 minutes, and 60 minutes (Tables 1 and 2) In the case of the topical composition), or after 30 minutes, 60 minutes, and 90 minutes (in the case of the topical composition in Table 3), self-reported feeling of cooling sensation (2 points or more in the above cooling sensation intensity test) The number of panelists who participated was counted. The number of subjects who self-reported that they felt a cold sensation was classified based on the following criteria, and the degree of persistence of cold sensation intensity was evaluated. The results are shown in Tables 1-3.
+++: 9-10 people
++: 6-8 people
+: 3 to 5 people
-: 0 to 2 people

<Component odor test>
A spray container was filled with the composition for external use, and 1 push (0.15 ml) was sprayed on the inside of the forearm of 20 panelists. Immediately after spraying, the panelists smelled the area around the sprayed area on the inner side of the forearm, and scored the strength of the component odor according to the following criteria. The component odor refers to the odor of the component itself, such as menthol, monomenthyl succinate, menthyl lactate, and menthyl acetate. Tables 1-3 show the total score of 20 people.
3 points: No component odor is felt at all
2 points: Slight component odor
1 point: component odor is felt
0 points: Perceives a strong component odor

<High temperature stability test>
The composition for external use was stored in an environment of 40°C for one week. A spray container was filled with the composition for external use after storage, and 1 push (0.15 ml) was sprayed on the inside of the forearm of 10 panelists. Immediately after spraying, when the panelists sniffed the area around the sprayed area on the inner side of the forearm, the strength of the offensive odor was scored based on the following criteria. The off-flavor refers to an odor that is not the odor of the component itself. Therefore, a higher score indicates higher high temperature stability.
3 points: No offensive odor at all
2 points: Slightly offensive odor
1 point: smell bad
0 points: strong odor

The scores of 10 panelists were averaged, and the average values were classified according to the following criteria to evaluate the degree of high-temperature stability. The results are shown in Tables 1-3.
◎: Score average value is 2.0 or more and 3.0 or less
○: score average value of 1.5 or more and less than 2.0
△: score average value of 1.0 or more and less than 1.5
×: score average value of 0 or more and less than 1.0

As is clear from Tables 1 to 3, topical compositions containing only menthol as a component other than the base material (Comparative Examples 1, 2, 16) and topical compositions containing only monomenthyl succinate (Comparative Examples 7, 10, 13). Compared to the longevity of the cooling sensation by the external composition containing menthol and monomenthyl succinate (Examples 1 to 5), the longevity of the cooling sensation was dramatically improved. On the other hand, topical compositions containing only menthol as a component other than the base material (Comparative Examples 1 and 2) and topical compositions containing only menthyl lactate or menthyl acetate (Comparative Examples 8, 9, 11, 12, 14, and 15). Compared to the longevity of the cool feeling by the topical composition containing menthyl lactate or menthyl acetate together with menthol (Comparative Examples 3 to 6), the longevity of the cool feeling is not improved, or even if it is improved, only an insufficient improvement effect is observed. However, it was inferior to the compositions for external use containing menthol and monomenthyl succinate (Examples 1 and 2). In addition, the effect of improving the cooling sensation lasting by containing monomenthyl succinate together with menthol was recognized as a dramatic effect despite the fact that the menthol content was very low (Examples 1 to 5, especially Examples 1 to 3). This indicates that the effect of monomenthyl succinate in improving the cooling sensation persistence is very large relative to the menthol content, that is, the cooling sensation persistence can be efficiently improved.

In addition, as is clear from Tables 1 to 3, the compositions for external use (Comparative Examples 1, 2, and 16) containing only menthol as a component other than the base material have good high-temperature stability, but lactic acid as a component other than the base material External compositions containing only menthyl or menthyl acetate (Comparative Examples 8, 9, 11, 12, 14, 15) have poor high-temperature stability. 6) had problems with high temperature stability. On the other hand, the topical compositions containing only monomenthyl succinate (Comparative Examples 7, 10, and 13) have good high-temperature stability. , good high temperature stability was observed.

[Test Example 2]
A topical composition having the composition shown in Table 4 was prepared. In Table 4, menthol is l-menthol and mono-menthyl succinate is mono-l-menthyl succinate. The prepared composition for external use was subjected to the following tests.

<Cooling intensity test (evaluation by rinse-off)>
A spray container was filled with the composition for external use, and 1 push (0.15 ml) was sprayed on the inside of the forearm of 10 panelists. The self-reported intensity of the cold feeling by the panelists immediately after drying with a towel was scored based on the following criteria.
3 points: feel a strong cold sensation
2 points: feeling cold
1 point: feel a slight cold sensation
0 points: No cold feeling at all

The number of panelists who gave a score of 2 or more was classified based on the following criteria, and the degree of cold sensation intensity was evaluated. The greater the number of +, the stronger the cooling sensation intensity. Table 4 shows the results.
+++: 9-10 people
++: 6-8 people
+: 3 to 5 people
-: 0 to 2 people

<Cool sensation persistence test (evaluation by rinse-off)>
In the above cold sensation strength test, the number of panelists who self-reported that they felt a cold sensation (2 points or more in the above cold sensation strength test) at 10, 20 and 30 minutes after towel drying was counted. The number of subjects who self-reported that they felt a cold sensation was classified based on the following criteria, and the degree of persistence of cold sensation intensity was evaluated. Table 4 shows the results.
+++: 9-10 people
++: 6-8 people
+: 3 to 5 people
-: 0 to 2 people

As is clear from Table 4, the external composition containing monomenthyl succinate together with menthol (Examples 6 to 10) compared to the external composition containing only menthol as a component other than the base material (Comparative Example 17). The cooling sensation persistence has improved dramatically. In addition, the topical compositions (Examples 6 to 9) further containing an amphiphilic ester together with menthol and monomenthyl succinate contained the amphiphilic ester, although the amphiphilic ester itself had no cooling sensation strength. Compared to the composition for external use without amphipathic ester (Example 10), the intensity of the lasting cooling sensation was enhanced, and the enhancement of the intensity of the lasting cooling sensation increased as the content of the amphipathic ester increased.

Claims (3)

(A) menthol, (B) monomenthyl succinate, and (C) bisethoxydiglycol cyclohexane-1,4-dicarboxylate ,
The content of the component (A) is 0.001 to 0.03% by weight,
A composition for external use , wherein the content of component (C) per 1 part by weight of component (A) is 280 to 600 parts by weight . The composition for external use according to claim 1, wherein the content of component (B) is 0.001 to 0.02% by weight. 3. The composition for external use according to claim 1 or 2 , which is used after being applied to the skin and then washed off.