JP3524445B2 - Freshener composition - Google Patents

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a refreshing agent composition and cosmetics, and more particularly to a refreshing agent composition and cosmetics which have no irritating sensation or peculiar odor and are excellent in sustaining the refreshing sensation.

[0002]

2. Description of the Related Art In recent years, in the field of cosmetics, research and development of "functional cosmetics" in line with the demand have been remarkable with the improvement of consumer awareness. For example, when categorized from the aspect of function according to item, skin care cosmetics mainly for moisturizing skin function, skin care cosmetics mainly for crude drug function, body care cosmetics, hair care cosmetics, hair styling agent, sunscreen agent, which appeal new functions, Permanent agents, bath agents, hair dyes, manicures and the like can be mentioned. In addition, cosmetics that give a cool sensation to the skin and mucous membranes as other functions not only have a physiological effect, but also have a psychological effect (edited by the Japan Cosmetic Science Society, functional cosmetics, published by CMC, 1990). .

Under such a background, menthol, camphor and the like are generally used as a refreshing agent for cosmetics and the like in order to give a cool sensation to the skin and mucous membranes. However, there was a defect that the refreshing feeling was not long-lasting. Therefore, the present inventors have attempted to improve these problems by using 2-hydroxymethyl-3,3,3 as a substance that has no irritating sensation or peculiar odor and maintains an excellent cooling sensation for a long time.
A refreshing feeling imparting agent containing 5,5-trimethylcyclohexanol and 2-hydroxymethyl-3,5,5, -trimethylcyclohexanol has been proposed (JP-A-9-
No. 208449).

However, 2-hydroxymethyl-
Cyclohexanol derivatives such as 3,3,5, -trimethylcyclohexanol and 2-hydroxymethyl-3,5,5, -trimethylcyclohexanol have high crystallinity and were used as an aqueous solution, an ethanol solution or a composition for external use on the skin. In this case, there was a problem that crystals were deposited over time. In addition, when used in a large amount as a composition for external use, there is a problem in the feeling of use such as stickiness.

[0005]

DISCLOSURE OF THE INVENTION The present invention provides 2-hydroxymethyl-3,3,5, -trimethylcyclohexanol and 2-hydroxy, which have no irritating sensation or peculiar odor and have a long-lasting excellent cooling sensation. It is an object of the present invention to provide a cooling agent composition which is stably blended with a cyclohexanol derivative such as methyl-3,5,5, -trimethylcyclohexanol and which has an excellent feeling in use.

[0006]

Means for Solving the Problems As a result of intensive studies for solving the above-mentioned object, the present inventors have found that 2-hydroxymethyl-3,3,5, -trimethylcyclohexanol, 2
By using a cyclohexanol derivative such as -hydroxymethyl-3,5,5, -trimethylcyclohexanol and a specific ester and polyhydric alcohol,
The present invention has been completed by finding that a cooling agent composition which has no irritating sensation and no specific odor and is excellent in durability of a refreshing feeling and the like, and which is excellent in stability over time and feeling in use is obtained.

That is, the present invention provides (A) one or more cyclohexanol derivatives represented by the following general formula (1), and (B) an alkyl lactate represented by the following general formula (2) or the following general formula. A cooling agent composition containing one or more selected from the group consisting of dibasic acid dialkyl esters represented by (3) and one or more selected from (C) polyhydric alcohols, and It's in cosmetics.

[0008]

[Chemical 7]

(In the formula, R ¹ is a methyl, ethyl or isopropyl group, and may have a hydroxyl group. Further, two R 1 s may be bonded to the same cyclic carbon atom.
² is CH ₂ OH, CH (OH) CH ₃ or C (OH) CH ₃
It is CH ₃ . m is an integer of 1 to 3. )

[0010]

[Chemical 8]

(In the formula, R ³ is a linear or branched alkyl group having 2 to 18 carbon atoms.)

[0012]

[Chemical 9]

(In the formula, R ⁴ and R ⁵ have 2 to 1 carbon atoms.
8 is an alkyl group, and n represents an integer of 2-8. )

The present invention also provides the above-mentioned cooling agent composition wherein (A) is 2-hydroxymethyl-3,3,5, -trimethylcyclohexanol or 2-hydroxymethyl-3,5,5, -trimethylcyclohexanol. It is in things.

[0015]

BEST MODE FOR CARRYING OUT THE INVENTION Embodiments of the present invention will be described in detail below.

The cyclohexanol derivative represented by the general formula (1) of the component (A) used in the present invention is:
2-hydroxymethyl-3,3,5-trimethylhexanol, 2-hydroxymethyl-3,5,5-trimethylcyclohexanol, 2-hydroxymethyl-3-methyl-6-isopropylcyclohexanol, 2-hydroxymethyl-3 -Isopropyl-6-methylcyclohexanol, 2- (1-hydroxyisopropyl) -5
-Methylcyclohexanol and the like can be mentioned, and they can be easily obtained by synthesizing by a known method or by extraction / separation from natural products.

For example, 2-hydroxymethyl-3,3
5-Trimethylcyclohexanol and 2-hydroxymethyl-3,5,5-trimethylcyclohexanol can be synthesized by the method described in JP-A-5-213802. It can also be obtained by reacting dihydroisophorone with ethyl formate, introducing a formyl group, and then reducing with a reducing agent such as lithium borohydride. 2-Hydroxymethyl-3-methyl-6-isopropylcyclohexanol can be obtained by ethoxycarbonylating menthone and then reducing it. 2- (1-Hydroxyisopropyl) -5-methylcyclohexanol can be obtained by mixing citronellal with an aqueous acid solution and stirring. Further, 2- (1-hydroxyisopropyl) -5-methylcyclohexanol can be obtained by extracting from eucalyptus leaves. These compounds have some stereoisomers, but they can be used as a mixture or each stereoisomer can be used alone. Among these, 2-hydroxymethyl-3,3,5, -trimethylcyclohexanol and 2
-Hydroxymethyl-3,5,5, -trimethylcyclohexanol is particularly preferable for a refreshing feeling.

Examples of the alkyl lactate represented by the general formula (2) of the component (B) used in the present invention include ethyl lactate, isobutyl lactate, lauryl lactate, myristyl lactate, cetyl lactate and octyl dodecyl lactate. Can be mentioned. Further, lauryl lactate and octyldodecyl lactate can be mentioned as preferable examples which are liquid at 20 ° C. and are widely used in cosmetics and the like. The dibasic acid diester represented by the general formula (3) includes diethyl succinate, dihexyl succinate, diisopropyl succinate, di2-diethylhexyl succinate, dipropyl adipate, diisopropyl adipate, diisobutyl adipate, Examples thereof include di-2-ethylhexyl adipate, diethyl sebacate, diisopropyl sebacate and the like. Further, it is liquid at 20 ° C. and is commonly used for cosmetics and the like, and preferable examples include di-2-ethylhexyl succinate, diisopropyl adipate, diisobutyl adipate, di2-ethylhexyl adipate, diethyl sebacate, diisopropyl sebacate and the like. Can be mentioned. One or more of these esters can be used in the cooling composition of the present invention.

As the polyhydric alcohol as the component (C) used in the present invention, ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, glycerin, diglycerin, polyglycerin, 1,3-butylene glycol etc. can be mentioned. One or two or more of these polyhydric alcohols can be used in the cooling composition of the present invention.

The blending amount in the cooling composition of the present invention varies depending on the conditions of use and the like, but the component (A) is 0.01 to 30% by weight (hereinafter referred to as wt%) based on the total amount of the final composition. It is preferable that the component (B) is 0.01 to 30 wt% and the component (C) is 0.1 to 30 wt%. Further, it is preferable that the blending amount of the component (B) with respect to the component (A) is 1/3 times or more, and if the blending amount is less than that, the effect of the present invention may not be sufficiently obtained.

The cooling composition of the present invention can be used in various forms such as an aqueous solution system, a solubilization system, an emulsion system and a dispersion system. In addition, as its usage, human skin, scalp,
Lotions, milk lotions, creams, packs, facial cleansers, bath agents, foundations, lipsticks, shampoos, rinses, hair treatments, toothpastes, oral coolers, colognes, and suppositories used for hair or oral cavity, etc. It can be used for products and pharmaceuticals.

If desired, the cooling composition of the present invention may contain components used in cosmetics, quasi drugs, pharmaceuticals, etc., as long as the effects of the present invention are not impaired. That is, oils and fats, pigments, fragrances, preservatives, surfactants, pigments, antioxidants, chelating agents, ultraviolet absorbers, ultraviolet scattering agents, polymeric sticky agents, inorganic salts, sugars, vitamins, plant extracts Etc. can be used.

[0023]

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

The test methods of the "crystal formation inhibition test" and the "sensory evaluation test" conducted in the present invention are as follows.

(Crystal Formation Inhibition Test) The test composition was placed in a glass container, sealed and stored at 0 ° C. and −10 ° C. for 2 weeks, and the formation of crystals was visually judged. The judgment criteria are as follows. ○: No crystal formation was observed △: Crystal formation was slightly observed ×: Crystals were considerably observed

(Sensory Evaluation Test) Ten test subjects applied the test composition to the intended site of the sample to give a “cool feeling”.
For each item of "sensation of stimulation" and "sensation of stickiness", the number of people who answered "feel a refreshing feeling", "not feel a feeling of irritation or peculiar odor", "not feel sticky", etc. is shown. Although some of the test compositions separated the oil component from the water, the tests were carried out by mixing by shaking.

Examples 1 to 3 and Comparative Examples 1 to 3 (Test composition) The test compositions shown in Table 1 were manufactured by a conventional method, and each of the above tests was carried out. The results are also shown in Table 1.
The numerical values in the table below represent wt%.

[0028]

[Table 1]

As shown in Table 1, the test composition of the present invention was compared with Comparative Examples which did not satisfy the essential components of the present invention.
All obtained excellent test results.

Examples 4 to 6 and Comparative Examples 4 and 5 (Test Composition) The test compositions shown in Table 2 were produced by a conventional method, and the above-mentioned respective tests were carried out. The results are also shown in Table 2.

[0031]

[Table 2]

As shown in Table 2, the test composition of the present invention was compared with Comparative Examples which did not satisfy the essential components of the present invention.
All obtained excellent test results.

Examples 7 to 9 and Comparative Example 6 (Test composition) The test compositions shown in Table 3 were manufactured by a conventional method, and each of the above tests was carried out. The results are also shown in Table 3.

[0034]

[Table 3]

As shown in Table 3, the test composition of the present invention was compared with Comparative Examples which did not satisfy the essential components of the present invention.
All obtained excellent test results.

Example 10 (Lotion) A lotion with the following composition was produced by a conventional method, and each of the above tests was carried out. As a result, no irritating sensation or peculiar odor was observed, a continuous excellent refreshing sensation was observed, no problem was observed in stability over time such as crystal formation, and the usability was sufficiently satisfactory.

[0037]             Ingredient name Example 10 2-hydroxymethyl-3,3,5     -Trimethylcyclohexanol 5.0 Octyl dodecyl lactate 3.0 Polyoxyethylene hydrogenated castor oil (80EO) 2.0 Glycerin 5.0 1,3-butylene glycol 5.0 Ethanol 10.0 Purified water residue

Example 11 (Cream) A cream having the following composition was produced by a conventional method and the above-mentioned tests were carried out. As a result, no irritating sensation or peculiar odor was observed, a continuous excellent refreshing sensation was observed, no problem was observed in stability over time such as crystal formation, and the usability was sufficiently satisfactory.

[0039]           Ingredient name Example 11 2-hydroxymethyl-3,3,5     -Trimethylcyclohexanol 2.0 2-hydroxymethyl-3,5,5,     -Trimethylcyclohexanol 8.0 Octyl dodecyl lactate 5.0 Di-2-ethylhexyl succinate 3.0 Diisopropyl adipate 2.0 Dipropylene glycol 10.0 Polyethylene glycol 200 10.0 Squalane 3.0 Vaseline 1.0 2-Methylhexyl paramethoxycinnamate 1.0 Glyceryl monostearate 1.0 Polyoxyethylene hydrogenated castor oil (40EO) 1.0 Carboxy vinyl polymer 0.5 Diisopropanolamine 0.2 Methyl paraoxybenzoate 0.1 Disodium edetate 0.1 Fragrance 0.5 Purified water residue

Example 12 (W / O sunscreen) A W / O sunscreen having the following composition was produced by a conventional method, and each of the above tests was carried out. As a result, no irritating sensation or peculiar odor was observed, a continuous excellent refreshing sensation was observed, no problem was observed in stability over time such as crystal formation, and the usability was sufficiently satisfactory.

[0041]           Ingredient name Example 12 Oil phase component   2- (1-hydroxyisopropyl)       -5-methylcyclohexanol 30.0   Octyl dodecyl lactate 30.0   4-tert-butyl-4 '       -Methoxybenzoylmethane 3.0   2-Ethylhexyl paramethoxycinnamate 2.0   Decamethylcyclopentasiloxane 10.0   Sorbitan monoisostearate 3.0   Palmitic acid 1.0 Water phase component   Ethanol 5.0   Diglycerin 5.0   Potassium hydroxide 0.2   Methyl paraoxybenzoate 0.1   Purified water residue

Example 13 (O / W Sunscreen) An O / W sunscreen having the following composition was produced by a conventional method, and each of the above tests was carried out. As a result, no irritating sensation or peculiar odor was observed, a continuous excellent refreshing sensation was observed, no problem was observed in stability over time such as crystal formation, and the usability was sufficiently satisfactory.

[0043]           Ingredient name Example 13 Oil phase component   2-hydroxymethyl-3-methyl       -6-Isopropylcyclohexanol 3.0   2-hydroxymethyl-3,3,5-trimethyl       Cyclohexanol 3.0   Di-2-ethylhexyl sebacate 2.0   Di-2-ethylhexyl adipate 2.0   2-Ethylhexyl paramethoxycinnamate 2.0   Octyldodecyl myristate 2.0   Cetanol 3.0   Sodium monoacyl glutamate 1.0   Glyceryl monostearate 2.0   Fine particle titanium oxide 2.0 Water phase component   Glycerin 10.0   Dipropylene glycol 10.0   Diglycerin 10.0   Titanium oxide sol 5.0   Purified water residue

[0044]

EFFECTS OF THE INVENTION As described above, the present invention has a cooling agent composition and a cosmetic composition which have no irritating sensation or peculiar odor and have a long-lasting refreshing sensation, and which are excellent in stability over time and usability. It is clear to provide.

─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Masafumi Yakumaru 5-3 28, Kotobuki-cho, Odawara-shi, Kanagawa, Kanebo Co., Ltd. (56) Reference JP-A-9-208449 (JP, A) Hei 7-118119 (JP, A) JP 5-295388 (JP, A) (58) Fields investigated (Int.Cl. ⁷ , DB name) A61K ^7/ 00-7/50

Claims (5)

(57) [Claims] 1. (A) one or more cyclohexanol derivatives represented by the following general formula (1), and (B) an alkyl lactate ester represented by the following general formula (2) or the following general formula (3): A cooling agent composition comprising one or more selected from the group consisting of dibasic acid dialkyl esters represented and one or more of (C) a polyhydric alcohol. [Chemical 1] (However, in the formula, R ¹ is a methyl group, an ethyl group, or an isopropyl group having or not having a hydroxyl group, and two or more R 1 may be bonded to the same cyclic carbon atom. R ² is CH ₂ OH or CH ₂ .
(OH) CH ₃ or C (OH) CH ₃ CH ₃ . m is an integer of 1 to 3. ) [Chemical 2] (However, in the formula, R ³ is a linear or branched alkyl group having 2 to 18 carbon atoms.) (However, in the formula, R ⁴ and R ⁵ are alkyl groups having 2 to 18 carbon atoms, and n is an integer of 2 to 8.) 2. (A) is 2-hydroxymethyl-3,
The cooling composition according to claim 1, which is 3,5, -trimethylcyclohexanol or 2-hydroxymethyl-3,5,5, -trimethylcyclohexanol. 3. The cooling composition according to claim 1, wherein (B) is liquid at 20 ° C. 4. The cooling agent composition according to claim 1, wherein the blending amount of the component (B) is 1/3 or more of the blending amount of (A). 5. (A) one or more cyclohexanol derivatives represented by the following general formula (1) and (B) an alkyl lactate represented by the following general formula (2) or the following general formula (3) A cosmetic comprising one or more kinds selected from the group consisting of dibasic acid dialkyl esters represented and one or more kinds of (C) polyhydric alcohol. [Chemical 4] (However, in the formula, R ¹ is a methyl group, an ethyl group, or an isopropyl group having or not having a hydroxyl group, and two or more R 1 may be bonded to the same cyclic carbon atom. R ² is CH ₂ OH or CH ₂ .
(OH) CH ₃ or C (OH) CH ₃ CH ₃ . m is an integer of 1 to 3. ) [Chemical 5] (In the formula, R ³ is a linear or branched alkyl group having 2 to 18 carbon atoms.) (However, in the formula, R ⁴ and R ⁵ are alkyl groups having 2 to 18 carbon atoms, and n is an integer of 2 to 8.)