JPH0967241A - Cosmetic - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a cosmetic containing an oil, low in irritation to eyes, excellent in feeling when coating on the skin, without a nasty smell after passage of time and readily emulsified or gelled. SOLUTION: This cosmetic contains 0.1-95wt.%, preferably 1-50wt.% of an asymmetric ether compound expressed by the formula: R<1> -O-R<2> (R<1> is a group of formula I, formula II or formula III; R<2> is an alkyl wherein total C-number of R<1> and R<2> is 16-28). Other than these, a well-known liquid oil widely used as a raw material of cosmetic (e.g.; squarane) is mixed. A mixing weight ratio of the asymmetric ether compound to the widely used oil is 0.01-20. A surfactant (e.g.; a nonionic surfactant) is preferably mixed to solubilize, emulsify or gelatinize the oil. The cosmetic can be mixed with the other cosmetic of oily, creamy, gel, emulsion-like, lotion-like, spray-like, pasty, solid and semi-solid, etc.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to cosmetics, and more specifically, an oil agent which has less irritation to the eyes, has a good feel when applied to the skin, does not change odor over time, and is easily emulsified or gelled. Related to cosmetics.

[0002]

2. Description of the Related Art
Liquid oils commonly used in cosmetics such as creams, emulsions and lotions include animal and vegetable oils such as squalane and jojoba oil or mineral oils such as liquid paraffin, oils and fats obtained by chemical synthesis such as isopropyl palmitate, and light polyisobutene. Known hydrocarbons and silicones such as dimethylpolysiloxane are known. The ideal properties of these liquid oils used in cosmetics are high safety, no color / smell, no coloring or odor over time, and excellent feel, moderately It can be mentioned that the viscosity is low.

[0003] On the other hand, cosmetics are not very unsatisfactory such as oily feeling in terms of performance, and since they are applied directly to the face, they are highly safe to the skin. In the unlikely event of accidental use and eye contact, eye safety must be considered. However, conventional oils have a small oily feeling and a good feel when the molecular weight is small, but the skin irritation is high and the irritation to the eyes is strong, and the one having a high molecular weight is a skin irritation or an eye irritation. Although the feeling of irritation is reduced, the oily feeling becomes strong and the feeling is unfavorable, and it is difficult to achieve both safety and feeling at the same time. Further, the ester oil has a problem in that it is colored or odor is changed with time due to hydrolysis or the like in the product, and the quality of the product is significantly deteriorated. Further, silicone oil is relatively satisfactory in terms of compatibility of safety and feel, coloring of the product over time, and odor, but compatibility with general-purpose cosmetic raw materials such as surfactants is poor, There were some difficulties in formulation such as difficulty in emulsification, solubilization, and gelation. As described above, the currently used general-purpose oils satisfy all of the points that they have no irritation to the eyes, have a good feel (no oily feeling, no stickiness), are easy to formulate, and do not have a color or odor. Is not found.

On the other hand, ether compounds are also known to be used as an oil agent for cosmetics and the like. For example, JP-A-48-5941 discloses a saturated β-position side chain monoether compound having 24 or more carbon atoms, and JP-A-48-33037 discloses a higher chain ether compound having 20 or more carbon atoms. In JP-A-63-122612 and JP-A-6-507654, one alkyl group of monoether has 6 to 6 carbon atoms.
An ether compound which is 22, US Pat. No. 4,900,254 discloses an ether compound in which one alkyl group has 1 to 3 carbon atoms and the other alkyl group has 8 to 20 carbon atoms.
However, these ether compounds also do not satisfy all the above properties as an oil agent for cosmetics.

Further, a general-purpose surfactant used together to emulsify or gel such a general-purpose oil agent, for example, glycerin monofatty acid ester, sorbitan monofatty acid ester used as an emulsifier, and soap used as an emulsion stabilizer. However, polyoxyethylene alkyl ethers and the like used as gelling agents have a considerable amount of irritation to the eyes, and caution has been required in their use.

[0006] Therefore, the object of the present invention is to provide a cosmetic containing an oily agent which has less irritation to the eyes, has a good feel when applied to the skin, does not change odor over time, and is easy to emulsify or gel. To do.

[0007]

In view of such circumstances, the inventors of the present invention have conducted diligent research and found that when a specific ether compound is used, the feeling of irritation to the eyes is small and the feeling when applied to the skin. The present invention has been completed by finding out that a cosmetic composition having good quality, easy emulsification and gelation, and having no odor change over time can be obtained. That is, the present invention relates to compounds of the general formula ^{(I) R 1 -O-R} 2 (I) wherein, R ¹ is formula

[0008]

[Chemical 7]

R ² represents a linear or branched alkyl group in which the total number of carbon atoms of R ¹ and R ² is 16 to 28. ] A cosmetic containing one or more asymmetric ether compounds represented by the above.

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION Embodiments of the present invention will be described in detail below. In the ether compound represented by the general formula (I), the total carbon number of R ¹ and R ² is 16 to 28, but if it is less than 16, irritation to the eyes occurs, and if it exceeds 28, it solidifies at room temperature. It is easy to do and is not preferable. In particular, when the total number of carbon atoms of R ¹ and R ² is 17 to 24, it is more preferable because it is less likely to volatilize at a high temperature and hard to solidify at a low temperature, thereby improving the stability of the product.

Examples of the ether compound represented by the general formula (I) include compounds represented by the general formula (II) or (III). In this case, it is preferable that R ⁴ is an ethyl group from the viewpoint of feeling.

[0012]

Embedded image

[Wherein R ³ has 10 to 22 carbon atoms, preferably 12 carbon atoms]
~ 18 straight or branched chain alkyl groups are shown. ]

[0014]

Embedded image

[In the formula, R ⁴ represents a methyl group or an ethyl group, and R ⁵ represents a linear or branched alkyl group having 13 to 25 carbon atoms, preferably 14 to 20 carbon atoms. ] As the linear or branched alkyl group having 10 to 22 carbon atoms represented by R ³ in the general formula (II), decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, Linear alkyl groups such as eicosyl and docosyl; mixed alkyl groups derived from coconut oil, tallow, etc .; 3,7-dimethyloctyl group, 2-butyloctyl group, 2- (3-methylbutyl) -1,6-dimethyl Hexyl group, 2-pentylnonyl group, 2-hexyldecyl group, 2-heptylundecyl group, emery type isostearyl group, 3- (1,3,3
-Trimethylbutyl) -5,7,7-branched alkyl groups such as trimethyloctyl group, 2-octyldodecyl group, and 2-nonyltridecyl group are mentioned, but a linear alkyl group is more preferable because an appropriate viscosity can be obtained. .

The number of carbon atoms represented by R ⁵ in the general formula (III)
As the linear or branched alkyl group of 13 to 25, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl,
Linear alkyl groups such as docosyl and tetracosyl; coconut oil,
Mixed alkyl groups derived from beef tallow, etc .; 2- (3-methylbutyl) -1,6-dimethylhexyl, 2-pentylnonyl group, 2-hexyldecyl group, 2-heptylundecyl group, emery-type isostearyl group, 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctyl group, 2
Examples thereof include branched-chain alkyl groups such as an -octyldodecyl group and a 2-nonyltridecyl group, but a linear alkyl group is more preferable because an appropriate viscosity can be obtained.

The asymmetric ether compound represented by the general formula (I), which is an essential component of the present invention, can be synthesized by a method generally used for the synthesis of lower alkyl ethers, for example, by reacting an alkyl halide with a metal alkoxide. Williamson's method, a method of reacting an alcohol and a carbonyl compound such as a ketone with a catalyst in a hydrogen atmosphere, an acid-catalyzed addition reaction of an alcohol and an olefin, or a method of reducing an ester compound. Although possible, the synthetic method is not limited to these.

The amount of the asymmetric ether compound represented by the general formula (I) in the cosmetic of the present invention is preferably 0.1 to 95% by weight, more preferably 1 to 50% by weight. If the content is less than 0.1% by weight, there are problems such as stickiness, which is not preferable in terms of feel. On the other hand, if it exceeds 95% by weight, gelation tends to occur and emulsification or the like becomes difficult, which is not preferable in production.

In addition to the asymmetric ether compound represented by the general formula (I), the cosmetic composition of the present invention contains one or more conventional liquid oil agents generally used as a raw material for cosmetics. It can be blended within a range that does not impair the effect. Such general-purpose oil agents include animal and vegetable oils such as squalane and jojoba oil or mineral oils such as liquid paraffin,
Examples include oils and fats obtained by chemical synthesis such as isopropyl palmitate, hydrocarbons such as light polyisobutene, and silicones such as dimethylpolysiloxane.

The blending amount of the above-mentioned general-purpose oil agent in the cosmetic of the present invention is not particularly limited, but the blending ratio A represented by the following formula:
That is, the blending weight ratio of the asymmetric ether compound represented by the general formula (I) and the general-purpose oil agent is preferably 0.01 to 20, and more preferably 0.1 to 10.

[0021]

[Equation 1]

In the cosmetic of the present invention, a general-purpose surfactant for solubilizing, emulsifying, or gelling the above-mentioned oily agent can be added within a range that does not impair the effects of the present invention.
As the surfactant used in the present invention, anionic,
Examples include amphoteric and nonionic surfactants. Examples of the anionic surfactant include sulfate-based surfactants such as alkyl sulfates and polyoxyethylene alkyl sulfates, sulfosuccinic acid-based, taurate-based, isethionate-based, α-based surfactants.
-Sulfonate type surfactant such as olefin sulfonic acid type; carboxylate type surfactant such as fatty acid soap type, ether carboxylic acid type and acylated amino acid type; phosphoric acid ester type surfactant such as alkyl phosphate type Can be mentioned. Examples of the amphoteric surfactant include carbobetaine-based, phosphobetaine-based, sulfobetaine-based, and imidazolinium betaine-based surfactants. Nonionic surfactants include polyoxyalkylene addition type, polyoxypropylene / polyoxyethylene addition type, amine oxide type, mono- or diethanolamide type, other sorbitan fatty acid ester, polyoxyethylene hydrogenated castor oil and its fatty acid ester. Polyethylene glycol fatty acid ester, glycerin fatty acid ester, sucrose fatty acid ester, polyether modified silicone, alkyl saccharide-based, N-polyhydroxyalkyl fatty acid amide-based polyhydric alcohol type surfactants, and the like. Among these surfactants, nonionic surfactants are preferable, and polyoxyethylene glycerin trifatty acid ester-based surfactants represented by the following general formula (IV) or general formula (V) are also represented. Polyoxyethylene hydrogenated castor oil fatty acid ester surfactants are preferred.

[0023]

Embedded image

(Wherein R ⁶ , R ⁷ , and R ⁸ are the same or different and each represents a straight-chain or branched-chain alkyl group having 11 to 23 carbon atoms, and p, q, and r are the average addition of ethylene oxide, respectively. (The number is 0 to 50, which represents the number of moles, and p + q + r is 5 to 50.)

[0025]

Embedded image

[Where X ¹ , X ² and X ³ are respectively expressed by

[0027]

[Chemical 12]

(Wherein R ⁹ , R ¹⁰ and R ¹¹ are the same or different and each represents a straight chain or branched chain alkyl group having 11 to 23 carbon atoms) and represents a fatty acid residue or a hydrogen atom. ,
At least one of X ¹ , X ² and X ³ is a fatty acid residue.
Each of s, t, and u is a number of 0 to 50, which represents the average number of moles of ethylene oxide added, and s + t + u is 5 to 50. ) In the compound represented by the general formula (IV), R ⁶ , R ⁷ and R ⁸ are the same or different and each represents a linear or branched alkyl group having 11 to 23 carbon atoms, but having 13 to 19 carbon atoms. The straight-chain or branched-chain alkyl group of 1 is more preferable in terms of formulation because it facilitates emulsification, dispersion and solubilization of the oil agent. Especially,

[0029]

Embedded image

Are both myristic acid residue, palmitic acid residue, stearic acid residue, 2-hexyldecanoic acid residue,
A fatty acid residue selected from a 2-heptylundecanoic acid residue, an emery-type isostearic acid residue, and a Nissan-type isostearic acid residue is more preferable for formulation because the emulsifying property and dispersibility in an oil agent are further improved. . Also,
Each of p, q, and r is a number from 0 to 50 that indicates the average number of moles of ethylene oxide added, and the total number of moles of ethylene oxide added, that is, p + q + r is 5 to 50.

In the compound represented by the general formula (V), X ¹ , X ² and X ³ are respectively

[0032]

Embedded image

A fatty acid residue or a hydrogen atom represented by is shown, and at least one of X ¹ , X ² and X ³ is a fatty acid residue. R ⁹ , R ¹⁰ and R ¹¹ are the same or different and have 11 to 11 carbon atoms.
23 straight or branched chain alkyl groups with 13 carbon atoms
A straight-chain or branched-chain alkyl group of -19 is more preferable from the viewpoint of formulation because it facilitates emulsification, dispersion and solubilization of the oil agent.
Especially,

[0034]

Embedded image

Are both myristic acid residues, palmitic acid residues, stearic acid residues, 2-hexyldecanoic acid residues,
A fatty acid residue selected from a 2-heptylundecanoic acid residue, an emery-type isostearic acid residue, and a Nissan-type isostearic acid residue is more preferable for formulation because the emulsifying property and dispersibility in an oil agent are further improved. . Also,
Each of s, t, and u is a number of 0 to 50 that represents the average number of moles of ethylene oxide added, and the total number of moles of ethylene oxide added, that is, s + t + u, is 5 to 50.

The blending amount of the surfactant in the cosmetic of the present invention is not particularly limited, but the blending ratio B represented by the following formula, that is, the asymmetric ether compound represented by the general formula (I) and the interface When the blending weight ratio to the active agent is 0.2 or more, the oily feeling is further reduced, and when it is 20 or less, emulsification is likely to occur, which is more preferable for formulation. More preferably, it is 0.5-10.

[0037]

[Equation 2]

In the cosmetic of the present invention, the asymmetric ether compound represented by the general formula (I) can be blended in any dosage form such as oil, cream, gel, emulsion, lotion, spray, Paste, solid,
A semi-solid state etc. are mentioned. Further, the mixed state of the asymmetric ether compound represented by the general formula (I) and the other components in these dosage forms may be any of homogeneous dissolution, emulsification, dispersion and separation.

In the cosmetic of the present invention, other general-purpose cosmetic raw materials can be added in order to obtain these dosage forms within a range that does not impair the effects of the present invention. Other cosmetic raw materials that can be incorporated into the cosmetic of the present invention include conventionally known creams, emulsions,
The raw materials blended in lotions, mascaras, lipsticks, etc. can be used. Specifically, ethylene glycol,
Diethylene glycol, triethylene glycol, higher polyethylene glycols, propylene glycol, dipropylene glycol, higher polypropylene glycols, butylene glycols such as 1,3-butylene glycol and 1,4-butylene glycol, glycerin, diglycerin , More polyglycerins, sugar alcohols such as sorbitol, mannitol, xylitol, maltitol, ethylene oxide of glycerins (hereinafter abbreviated as EO), propylene oxide (hereinafter P
Abbreviated as O), adducts, EO and PO adducts of sugar alcohols, monosaccharides such as galactose, glucose and fructose and their EO and PO adducts, and polysaccharides such as maltose and lactose and their EO and PO adducts. Polyhydric alcohols; oily components such as higher fatty acids such as isostearic acid and oleic acid; surfactants such as POE alkyl ethers, POE branched alkyl ethers, POE sorbitan esters, sorbitan esters, glycerin fatty acid esters, polyglycerin fatty acid esters; vitamins , Antibacterial agents such as triclosan and trichlorocarban, anti-inflammatory agents such as dipotassium glycyrrhizinate and tocopherol acetate, antidandruff agents such as zinc pyrithione and octopirox, activators, agents such as UV absorbers, preservatives such as methylparaben and butylparaben Agent, Le Kill amine oxide, foam boosters such as fatty acid alkanolamides, inorganic salts, viscosity modifiers such as polyethylene glycol stearate ethanol, pearling agents, perfumes, dyes, antioxidants, montmorillonite, saponite, Hekuraito, Veegum, Kunibia,
Water-swelling clay minerals such as smectons; polysaccharides such as carrageenan, xanthan gum, sodium alginate, pullulan, methylcellulose, carboxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, other high polymers such as carboxyvinyl polymers and polyvinylpyrrolidone Molecular substances: extender pigments such as titanium oxide, kaolin, mica, sericite, zinc white, and talc, and pigments such as polymer powders such as polymethylmethacrylic acid and nylon powder.

[0040]

[Examples] The present invention is described in more detail below by showing Examples of cosmetics of the present invention and synthetic examples of asymmetric ether compounds used in the present invention, but the present invention is not limited to these Examples. Not something.

Synthesis Example 1 Synthesis of 1,3-dimethylbutyl dodecyl ether

[0042]

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In a 500 ml flask equipped with a dropping funnel, a nitrogen gas introducing tube, a cooling tube and a stirrer, 4-methyl-2-
Pentanol (71.4 g, 0.7 mol) and particulate sodium hydroxide (36 g, 0.9 mol) were charged, and nitrogen gas was introduced at 80 ° C. for 1 hour.
Stir for hours. Then, dodecyl bromide 224 g (0.9
Mol) was added dropwise over 1 hour and the temperature was raised to 100 ° C.
It was stirred for 16 hours. After completion of the reaction, the reaction mixture was washed with water to remove excess sodium hydroxide and the formed salt, and excess 4-methyl-2-pentanol and dodecyl bromide were removed under reduced pressure, and further distilled under reduced pressure (102 ° C). / 0.
25 Torr) to obtain 40 g (0.15 mol) of the target 1,3-dimethylbutyl dodecyl ether as a colorless transparent liquid. The isolation yield was 21%.

Synthesis Example 2 Synthesis of 1,3-dimethylbutyl tetradecyl ether

[0045]

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500 equipped with a hydrogen gas inlet tube and a stirrer
107 g of tetradecyl alcohol in a ml autoclave
(0.5 mol), 100 g (1.0 mol) of 4-methyl-2-pentanone and 2.1 g of 5% Pd-C (pH 6.6) as a catalyst were charged, and the mixture was stirred at 150 ° C for 8 hours under a hydrogen pressure of 100 kg / cm ^2. It was After completion of the reaction, the catalyst was removed by filtration, and excess 4-methyl-2-pentanone was removed under reduced pressure. Further, vacuum distillation (143 ° C./1 Torr) was performed to obtain 112 g (0.38 mol) of the target 1,3-dimethylbutyl tetradecyl ether as a colorless transparent liquid. The isolation yield was 75%.

Synthesis Example 3 Synthesis of 1,3-dimethylbutyl hexadecyl ether

[0048]

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500 equipped with a hydrogen gas inlet tube and a stirrer
121 g of hexadecyl alcohol in a ml autoclave
(0.5 mol), 4-methyl-2-pentanone 100 g (1.0 mol), and 5% Pd-C (pH 6.6) 2.4 g as a catalyst were charged, and the mixture was stirred at 150 ° C. for 8 hours under a hydrogen pressure of 100 kg / cm ^2. It was After completion of the reaction, the catalyst was removed by filtration, and excess 4-methyl-2-pentanone was removed under reduced pressure. Further, vacuum distillation (142 ° C./0.6 Torr) was performed to obtain 114 g (0.35 mol) of the target 1,3-dimethylbutyl hexadecyl ether as a colorless transparent liquid. The isolation yield was 70%.

Synthesis Example 4 Synthesis of 1,3-dimethylbutyl octadecyl ether

[0051]

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4-methyl-2- was added to a 500 ml flask equipped with a dropping funnel, a nitrogen gas introducing tube, a cooling tube and a stirring device.
Pentanol 51g (0.5mol), particulate sodium hydroxide
26 g (0.65 mol) was charged, and 1 at 80 ° C under nitrogen gas introduction.
Stir for hours. Then, octadecyl bromide 216g
(0.65 mol) was added dropwise over 1 hour, the temperature was further raised to 100 ° C., and the mixture was stirred for 20 hours. After completion of the reaction, the reaction mixture was washed with water to remove excess sodium hydroxide and the produced salt, and excess 4-methyl-2-pentanol and octadecyl bromide were removed under reduced pressure. This was further purified by silica gel column chromatography to obtain the desired 1,3-dimethylbutyl octadecyl ether 27 g.
(0.075 mol) was obtained as a colorless transparent liquid. The isolation yield was 15%.

Synthesis Example 5 Synthesis of isopropyl tetradecyl ether

[0054]

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500 equipped with a hydrogen gas inlet tube and a stirrer
107 g of tetradecyl alcohol in a ml autoclave
(0.5 mol), 87 g of acetone (1.5 mol), 5% as a catalyst
2.1 g of Pd-C (pH 4.0) was charged, and the hydrogen pressure was 100 kg / c.
The mixture was stirred at 150 ° C. for 8 hours under m ² . After the reaction was completed, the catalyst was removed by filtration, and excess acetone was removed under reduced pressure. Furthermore, the product was purified by silica gel column chromatography to obtain the desired isopropyl tetradecyl ether 92
g (0.36 mol) was obtained as a colorless transparent liquid. The isolation yield was 72%.

Synthesis Example 6 Synthesis of 1-methylpropyl tetradecyl ether

[0057]

[Chemical 21]

2-butanol 37 was added to a 500 ml flask equipped with a dropping funnel, a nitrogen gas introducing tube, a cooling tube and a stirrer.
g (0.5 mol), particulate sodium hydroxide 32 g (0.8 mol)
Was charged, and the mixture was stirred at 80 ° C. for 1 hour while introducing nitrogen gas. Then, 222 g (0.8 mol) of tetradecyl bromide was added dropwise over 1 hour, the temperature was further raised to 100 ° C., and the mixture was stirred for 20 hours. After completion of the reaction, the reaction mixture was washed with water to remove excess sodium hydroxide and the formed salt, and to further excess 2-
Remove butanol and tetradecyl bromide under reduced pressure,
Further purify by silica gel column chromatography to obtain the desired 1-methylpropyl tetradecyl ether 35
g (0.13 mol) was obtained as a colorless transparent liquid. The isolation yield was 25%.

Synthesis Example 7 Synthesis of 1-methylpropyl octadecyl ether

[0060]

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500 equipped with hydrogen gas inlet tube and stirrer
135 g of octadecyl alcohol in a ml autoclave
(0.5 mol), 100 g (1.0 mol) of methyl ethyl ketone, and 2.7 g of 5% Pd-C (pH 4.0) as a catalyst were charged, and the mixture was stirred at 150 ° C. for 8 hours under a hydrogen pressure of 100 kg / cm ² . After completion of the reaction, the catalyst was removed by filtration, and excess methyl ethyl ketone was removed under reduced pressure. Vacuum distillation (160 ℃ / 0.35
Torr) was performed to obtain 109 g (0.33 mol) of the target 1-methylpropyl octadecyl ether as a colorless transparent liquid. The isolation yield was 66%.

Example 1 An O / W type emollient emulsion of the present invention having the composition shown in Table 1 and a comparative O / W type emollient emulsion having the composition shown in Table 2 were produced by the following method, and the touch and the eye were evaluated. The following methods were used to evaluate changes in sensation and odor. Further, the emulsifiability of the oil agent was evaluated by the following method by observing the appearance of these emulsions. The results are shown in Tables 1 and 2.

<Method for producing O / W type emollient emulsion> To 5 g of each oil, 1.8 g of polyoxyethylene (20) glyceryl triisostearate and 0.2 g of polyoxyethylene (30) glyceryl triisostearate were added,
Stir while heating (70 ° C) (oil phase). In a separate container, 88.3 g of purified water and other components are heated and dissolved by stirring (70 ° C), and this aqueous solution is added to the above oil phase with stirring to emulsify and cool to obtain an O / W type emollient emulsion. It was

<Evaluation method> (1) Feeling evaluation Ten professional panelists applied 2 g of each emulsion to the entire face including the area around the eyes, and after drying, the stickiness was evaluated according to the following criteria, and 10 people were evaluated. The average of the panelists' scores is
Those with a score of 1.4 or more were passed (○), and those with a score less than 1.4 were rejected (×). Non-greasy: 2 points Slightly sticky: 1 point Sticky: 0 points (2) Eye irritation At the same time as the above tactile evaluation, the presence or absence of eye irritation was also evaluated. The case where all 10 people answered that they did not have a feeling of irritation was judged as pass (○), and the case where even 10 people answered that there was a feeling of irritation was judged as fail (x). (3) Emulsifying property of oil agent The appearance of the emulsion was evaluated according to the following criteria, and the emulsifying property of the oil agent was visually judged. Emulsified (uniform turbidity): ○ Not emulsified (separation): × (4) Odor change Emulsion was stored at 50 ° C for 1 week, and odor was evaluated by the following criteria by 5 expert panelists. Persons with an average panel score of 1.6 or more were passed (○), and those below 1.6 were rejected (×).

No change: 2 Some change: 1 Change: 0

[0066]

[Table 1]

[0067]

[Table 2]

Note) * 1: Emalex GWIS 320, product name of Nippon Emulsion Co., Ltd. * 2: Emalex GWIS 330, product name of Japan Emulsion Co., Ltd. * 3: Pearlream Ex, product of Nippon Oil & Fats Co., Ltd. Product name * 4: TIO, product name of Nisshin Oil Co., Ltd. * 5: Sarakos 99, product name of Nisshin Oil Co., Ltd. * 6: Silicone SH-244, product name of Toray Silicone Co., Ltd. Example 2 An O / W type emollient cream having the composition shown in Table 3 was prepared. When this O / W type emollient cream was applied to the face, there was no irritation to the eyes even when applied around the eyes, and there was no unpleasant stickiness after use during use.

[0069]

[Table 3]

Note) * 7: Emarex RWIS 110, Nippon Emulsion Co., Ltd.
Product name * 2: Same as in Table 1 * 8: Leodol Super TWS-120, product name manufactured by Kao Corporation Example 3 A semitransparent lotion having the composition shown in Table 4 was prepared. When this semi-transparent lotion was applied to the face, there was no irritation to the eyes even when applied around the eyes, and there was no unpleasant stickiness after use during use.

[0071]

[Table 4]

Note) * 1: Same as Table 1 Example 4 W / O type emollient lotion having the composition shown in Table 5 was prepared. When this W / O type emollient lotion was applied to the face, there was no irritation to the eyes even when applied around the eyes, and there was no unpleasant stickiness after use during use.

[0073]

[Table 5]

Note) * 9: Silicone KF-96 (6cs), Shin-Etsu Silicone Co., Ltd.
Product name * 10: Emalex GWS-310, Nippon Emulsion Co., Ltd.
Product name * 8: Same as in Table 3 * 11: Emalex OD20, product name by Nippon Emulsion Co., Ltd. Example 5 A W / O emulsion type foundation having the composition shown in Table 6 was prepared. When this W / O emulsion type foundation was applied to the face, there was no irritation to the eyes even when applied around the eyes, and there was no unpleasant stickiness after use.

[0075]

[Table 6]

Note) * 6: Same as Table 2 Example 6 Oily mascara having the composition shown in Table 7 was prepared. When this oily mascara was applied to makeup eyelashes, there was no irritation to the eyes and no unpleasant stickiness after use.

[0077]

[Table 7]

Note) * 7: Same as Table 3 Example 7 A lipstick having the composition shown in Table 8 was prepared. This lipstick is
It spreads well during use and did not have any unpleasant stickiness.

[0079]

[Table 8]

Example 8 A transparent emollient lotion having the composition shown in Table 9 was prepared. When this transparent emollient lotion was applied to the face, there was no irritation to the eyes even when applied around the eyes, and there was no unpleasant stickiness after use during use.

[0081]

[Table 9]

Claims (6)

[Claims] 1. A compound represented by the general formula (I) R ¹ —O—R ² (I) [wherein R ¹ is a group represented by the following formula: Represents a group represented by, R ² is a total carbon number of R ¹ and R ² is 16 ~
28 represents a straight chain or branched chain alkyl group. ]
A cosmetic comprising one or more asymmetric ether compounds represented by: 2. The cosmetic according to claim 1, wherein the asymmetric ether compound represented by the general formula (I) is a compound represented by the general formula (II). Embedded image [In the formula, R ³ represents a linear or branched alkyl group having 10 to 22 carbon atoms. ] 3. The cosmetic according to claim 1, wherein the asymmetric ether compound represented by the general formula (I) is a compound represented by the general formula (III). Embedded image [In the formula, R ⁴ is a methyl group or an ethyl group, and R ⁵ has 13 to 25 carbon atoms.
Is a linear or branched alkyl group. ] 4. The cosmetic according to claim 1, which contains one or more general-purpose liquid oil agents as a cosmetic raw material. 5. The cosmetic according to claim 1, which contains one or more nonionic surfactants. 6. The nonionic surfactant is a polyoxyethylene glycerin trifatty acid ester-based surfactant represented by the general formula (IV), or a polyoxyethylene hydrogenated castor oil fatty acid ester represented by the general formula (V). The cosmetic according to claim 5, which is a surfactant. Embedded image (Here, R ⁶ , R ⁷ , and R ⁸ are the same or different and have 11 carbon atoms.
~ 23 linear or branched alkyl groups, p, q, r
Are numbers of 0 to 50 each showing the average number of moles of ethylene oxide added, and p + q + r is 5 to 50. ) [Chemical 5] [Where X ¹ , X ² and X ³ are respectively represented by the formula: (Here, R ⁹ , R ¹⁰ and R ¹¹ are the same or different and have a carbon number of 11
23 represents a straight chain or branched chain alkyl group. ) Represents a fatty acid residue or a hydrogen atom, and at least one of X ¹ , X ² and X ³ is a fatty acid residue. s, t, and u each represent the average number of moles of ethylene oxide added, 0 to 50
S + t + u is 5 to 50. )