JPH0331187B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a novel terpene alcohol glyceryl ether and cosmetics containing the same. Conventionally, α-monoalkylglyceryl ethers include palmitylglyceryl ether (referred to as chimyl alcohol), which exists in fish lipids;
Stearyl glyceryl ether (referred to as batyl alcohol), oleyl glyceryl ether (referred to as ceraryl alcohol), etc. are known, and these have excellent performance as emulsifiers, especially W/O type emulsion stabilizers, and It is known to have pharmacological effects such as blood cell production promoting effect in the bone marrow, anti-inflammatory effect, and anti-tumor activity (Japanese Patent Publications No. 10724/1982 and No. 18171/1982). However, these known α-monoalkylglyceryl ethers have drawbacks such as being a solid with a high melting point and being irritating to the skin. Studies have been conducted to improve these drawbacks; for example, α-monoalkylglyceryl ether using a long-chain alkyl group having a linear or branched substituent at the β-position has been proposed. (Japanese Patent Application Laid-open No. 12109/1983). However, although this product solved the above-mentioned drawbacks to some extent, it had new drawbacks such as decreased hydrophilicity and impaired emulsion stability. Therefore, the present inventors conducted research to overcome the above-mentioned drawbacks of known α-monoalkylglyceryl ethers, and found that they are liquid at room temperature, chemically stable, have excellent emulsion stability, and are resistant to skin irritation. Not α
- As a monoalkyl glyceryl ether, α- represented by the formula () having a methyl branch in the main chain
He proposed mono(methyl-branched alkyl)glyceryl ether (Special Publication No. 36260/1983). (In the formula, m is an integer from 2 to 14, and n is from 3 to
11, and the sum of m and n is 9 to 21) However, the above α-mono(methyl branched alkyl) glyceryl ether ( Since it is a complex mixture whose main component is ether (approximately 75% content), if the composition of the alkyl group changes, there is a risk that it will be difficult to obtain the desired performance or physical properties. It had the disadvantage that it was difficult to manage. On the other hand, in the natural world, polyprenyl compounds (terpene compounds) consisting of repeating isoprene units exist in a wide variety of forms as compounds with multiple methyl branches (maintaining a regular positional relationship) in the alkyl main chain. ing. It is well known that these polyprenyl compounds are widely used in the fields of fragrances, industrial chemicals, pharmaceuticals, cosmetics, foods, and the like. Particularly in recent years, knowledge has been discovered in various fields that polyprenyl compounds have important pharmacological effects, and efforts are being made to apply this to pharmaceuticals such as antitumor agents (Japanese Patent Publication No. 13823/1983).
JP-A-57-192343, JP-A No. 57-192342, JP-A No. 57-
No. 192341, No. 57-192340, No. 57-192339, No. 192341, No. 57-192340, No. 57-192339, No.
No. 57-106618, No. 54-89035, No. 54-5043,
No. 53-96330, etc.). Under these circumstances, the present inventors conducted intensive research on the surface chemistry of the above polyprenyl compounds, particularly on their application to emulsifiers, and found that glyceryl ethers derived from specific terpene alcohols are similar to conventional α-monoalkylglyceryls. The present invention was completed based on the discovery that it has excellent properties not found in ether and is useful as a cosmetic ingredient. Therefore, the present invention provides the following general formula () [In the formula, R is the following formula (m represents an integer from 1 to 10, A and B each represent a hydrogen atom, or both together form a single bond, and when m is 2 or more, A and B are The present invention provides a glycenyl ether of a terpene alcohol represented by the following formula (which may be a combination of two cases) and a cosmetic containing the same. Conventionally, glyceryl ethers derived from terpene alcohols include glyceryl ethers of alicyclic terpene alcohols (West German Patent No.
711916), mono- and diphytanyl glyceryl ethers (3-0-[3',7',11',15'-tetramethylhexadecyl]glycerol and 2,3-di-
0-[3′,7′,11′,15′-tetramethylhexadecyl]glycerol) (Biochemistry, Vol. 4,
pp. 1595-1599 (1965); Journal of Lipid
Research, Vol. 9, pp. 782-788 (1968)). However, the glyceryl ether of terpene alcohol of the present invention is a new compound that has a different structure from the above-mentioned known compounds and has not been described in any literature. The terpene alcohol glyceryl ether () of the present invention is produced, for example, by the following method. (In the formula, R ₁ is a hydrogen atom or a hydrocarbon group, R ₂ is a hydrocarbon group, R ₃ is a hydrocarbon group having 1 to 5 carbon atoms,
(X represents a halogen atom, R represents the same as above) In the present invention, when producing glyceryl ether of a terpene alcohol (for example, falnesol, etc.) containing multiple unsaturated bonds, method B is used. preferable. That is, method A involves ring-opening addition of a carbonyl compound to glycidyl ether () in the presence of a Lewis acid catalyst to produce 1,3-dioxolane (), which is then hydrolyzed in an acidic aqueous solution to obtain glyceryl ether (). It's a method. However, since this method involves two steps of reaction under acidic conditions, there is a risk that the isomerization, rearrangement, polymerization, etc. of unsaturated bonds caused by the acid catalyst may occur, resulting in a decrease in the yield of glyceryl ether (). On the other hand, method B allows highly pure glyceryl ether (2) to be obtained in high yield with simple operations. Method B will be explained in detail below. First, glycidyl ether () is produced by Williamson type ether synthesis of terpene alcohol () and epihalohydrin. The starting material, terpene alcohol, is expressed by the following formula () (In the formula, A, B and m are the same as above), and industrially easily available products include, for example, falnesol

[Formula] phytol

[Formula] etc. are exemplified. This ether synthesis reaction is carried out by a method known per se using a phase transfer catalyst. That is,
30~ for alkaline substances such as alkali metal hydroxides
Terpene alcohol () and epihalohydrin (preferably epichlorohydrin) are reacted in a 60% aqueous solution using a quaternary onium salt (industrially preferred is a quaternary ammonium salt) as a phase transfer catalyst. The amount of the alkaline substance is 1 to 10 mol, preferably 3 to 6 mol, per 1 mol of ().
The quaternary onium salt is 0.01 to 0.20 mol, preferably
0.05 to 0.10 mol, epihalohydrin is used in an amount of 1 to 10 mol, preferably 2 to 4 mol. The reaction temperature is preferably 30 to 80°C, especially 45 to 60°C, and a solvent is not necessary, but hydrocarbons such as hexane, heptane, benzene, toluene, xylene, etc., ether, and tetrahydrofuran (THF) that are inert to the reaction are used. , diglyme, dioxane and the like can also be used. When doing so, glycidyl ether () is obtained in a yield of 80-85% based on (). To obtain glycerol diester () from glycidyl ether (), lower fatty acid anhydride is reacted with () in the presence of a basic catalyst. Examples of the basic catalyst include tertiary amines such as triethylamine, tripropylamine, tributylamine, trioctylamine, pyridine, dimethylaniline, quinoline, and tetramethyl-1,6-diaminohexane. In addition, lower fatty acid anhydrides include acetic anhydride, propionic anhydride,
Examples include butyric anhydride, but acetic anhydride is particularly preferred. The reaction is carried out using 1 to 30 moles of acid anhydride, preferably 1 to 30 moles, per 1 mole of glycicyl ether ().
15 mol, base catalyst 0.01-0.20 mol, preferably
Use 0.05-0.10 mol, reaction temperature 70-150℃,
Preferably it is carried out at 80-120°C. Although a solvent may not be used, an inert solvent may be used if necessary. In this way, glycerol diester () can be obtained with a yield of 90 to 95% based on (). Hydrolysis of glycerol diester () is
This is carried out by a method known per se. That is, () may be added to an aqueous solution of an alkaline substance such as an alkali metal hydroxide, and a heating reaction may be caused. The amount of alkaline substances is not particularly limited, but ()
It is used in an amount of 2 mol or more, preferably 2 to 5 mol, per 1 mol. The reaction proceeds in an aqueous solution, using a water-soluble solvent such as lower alcohols such as methanol, ethanol, and isopropanol, and ethers such as THF and dioxane at 50 to 100°C.
Heating under reflux gives good results. When doing so, the desired glyceryl ether () is obtained in quantitative yield. The glyceryl ether () of the present invention is chemically stable because it does not have easily decomposable bonds such as ester groups in its molecular structure, causes less skin irritation, and has surfactant ability. It is particularly useful as a component of cosmetics, such as emulsifiers, oil agents (emollients), humectants, and thickeners. The properties of typical compounds of the present invention are as follows.

[Table] * Concentration of glyceryl ether The glyceryl ether of the present invention has polar groups such as hydroxyl groups, so it is hydrophilic and hygroscopic.
In addition, while it has good adsorption to the skin, the number of methyl branches in the alkyl chain moiety is greater than that of conventional glyceryl ethers, as well as double bonds, which hinders the arrangement of molecules in aqueous solutions. This makes it difficult to form aggregates such as liquid crystals, making it less soluble in water and appearing more oil-like. Therefore, when the compound of the present invention is blended into cosmetics and applied to the skin, it has strong resistance to washing,
It exhibits a characteristic that it remains highly persistent on the skin, that is, it has an excellent long-lasting effect as a cosmetic. Therefore, the products of the present invention are particularly useful as emollients and humectants in cosmetics. Further, among the compounds of the present invention, those having a relatively large number of carbon atoms in the alkyl group, such as phyteyl blyceryl ether, are also useful as lipophilic surfactants and emulsifiers that give water-in-oil emulsions. The amount of the glyceryl ether of the present invention to be incorporated into cosmetics may vary depending on various factors, but the appropriate amount is 0.2 to 15% by weight when used as an emulsifier, and 2 to 50% by weight when used as an oil or moisturizing agent. It is. The present invention will be explained in more detail below, but the present invention is not limited to these Examples. Example 1 Synthesis of farnersyl glyceryl ether: (i) In a reaction vessel equipped with a reflux condenser, a dropping funnel, a thermometer, and a stirrer, 360 g of a 50% aqueous sodium hydroxide solution (180 g as sodium hydroxide) was added.
[4.5 mol]), 333.6 g (1.5 mol) of falnesol, and 340 g of hexane are added and stirred vigorously. Next, 50.9 g of 50% tetrabutylammonium hydrogen sulfate (25.5 g as hydrogen sulfate)
[0.075 mol]) is added. While keeping the temperature of the reaction mixture at room temperature, 277.5 g (3.0 mol) of epichlorohydrin was added dropwise from the dropping funnel over about 30 minutes. During this time, the reaction mixture gradually becomes exothermic. After the dropwise addition is completed, the temperature of the reaction mixture is maintained at 50-55°C and stirring is continued for about 3 hours. It was confirmed by gas chromatography that falnesol had almost disappeared. To the reaction product, tap water 670
Add g and stir. Then, the hexane layer is collected by liquid separation. Hexane was distilled off under reduced pressure.
The residue is subjected to vacuum distillation. 352 g of falnesyl glycidyl ether was obtained as a colorless and transparent solution. yield
84%. Boiling point 155-160℃/0.6mmHg Elemental analysis As C ₁₈ H ₃₀ O ₂ (calculated value) C.77.6% (77.65%); H.10.6% (10.86%) O.11.7% (11.49%) Oxirane oxygen 5.62% (5.70%) Iodine value 273 (273.6) IR (cm ^-1 , liquid film) 3060, 2975, 2930, 2860,
1670, 1445, 1375, 1250, 1160〜1040,
1000 to 900, 835. ¹ H-NMR (δin ppm, CDCl ₃ , TMS internal standard) 1.60, 1.70, 1.75 (both singlet, 12H, 4 methyl groups) 1.85 to 2.30 (multiplet, 8H, methylene group) ) 2.40~2.90 (multiplet, 2H,

[Formula]) 2.95 to 3.30 (multiple line, 1H,

[Formula]) 3.35 to 3.80 (multiplet, 2H,

[Formula]) 4.03 (double line, 2H, J=6.5Hz

[Formula]) 4.90-5.50 (multiplet, 3H, olefin proton) (ii) Into a reaction vessel equipped with a reflux condenser, a dropping funnel, a thermometer, and a stirrer, 102 g of acetic anhydride (1.0
mol) and 2.0 g (0.02 mol) of triethylamine were added, and the mixture was heated to 90°C while stirring. Then, from the dropping funnel, 55.7 g (0.2 mol) of Farner glycidyl ether obtained in (i) of Example 1 was added.
drip over 40 minutes. During this time, heat is applied appropriately to maintain the temperature of the reaction mixture at 90 to 100°C. After the glycidyl ether was added dropwise, the reaction was continued at 120°C for another 4 hours. A gas chromatograph of the reaction mixture revealed that glycidyl ether had completely disappeared. Then, excess acetic anhydride is distilled off from the reaction mixture under reduced pressure. Then, dilute hydrochloric acid is added to neutralize triethylamine. After the organic matter is extracted by ether extraction, the ether is distilled off. The residue is then subjected to vacuum distillation. 75.6 g of phalnesylglycerol diacetate was obtained as a colorless and transparent liquid product. Yield 99.5%. Boiling point 195-199℃ (0.6mmHg) Elemental analysis C ₂₂ H ₃₆ O as ₅ (calculated value) C.69.2% (69.5%); H.9.80% (9.50%), O.20.7% (21.1%) Saponification Value 297 (295) Iodine value 207 (200) IR (cm ^-1 , liquid film) 2970, 2925, 2855, 1740,
(νC=O), 1660, 1440, 1365, 1220,
1160-1000, 835 ¹ H-NMR (δin ppm, CDCl ₃ , TMS internal standard) 1.60, 1.68, 1.75 (both singlet, 12H, 4 methyl groups) 1.85-2.20 (multiplet, 14H, methylene group + 2 COC H ₃ ) 3.50 (double line,
2H, J=5.0Hz

[Formula]) 4.0 (double line, 2H, J=6.0Hz-C H
₂ OCH ₂ CHOAcCH ₂ OCc) 3.80 to 4.55 (multiplet, 3H, -CH ₂ OCH ₂ C H OAcC H ₂ OAc)
4.90 to 5.50 (multiplet, 3H, olefin proton) (iii) Into a reaction vessel equipped with a reflux condenser, a dropping funnel, a thermometer, and a stirrer, 64.9 g of a 30% aqueous sodium hydroxide solution (19.5 g as sodium hydroxide)
g [0.487 mol]), add 200 ml of ethanol and stir. Next, (ii) of Example 1 was added from the dropping funnel.
Falnesylglycerol diacetate obtained from
61.7 g (0.162 mol) is added dropwise over about 20 minutes. The reaction mixture is then heated to reflux (3 hours) at 80°C. The reaction product becomes a homogeneous clear solution. After cooling, tap water 200g, ether 500g
ml for ether extraction. An ether layer is obtained by separation. Ether was distilled off under reduced pressure, and the residue was further dried at 60 to 80°C (3 hours) at 1 mmHg to obtain 47 g of falnesyl glyceryl ether in the form of a colorless and transparent liquid. Yield 97.9%. Elemental analysis as C ₁₈ H ₃₂ O ₃ (calculated value) C.73.2% (72.93%); H.11.0% (10.88%) O.16.5% (16.19%) Hydroxyl value 372.8 (378.5) Iodine value 254 (256.8) IR (cm ^-1 , liquid film) 3650-3100, 2975, 2925,
2860, 1660, 1440, 1370, 1100, 1080～
1000, 820 ¹ H-NMR (δin ppm, CDCl ₃ , TMS internal standard) 1.67, 1.70, 1.75 (both singlet, 12H, 4 methyl groups) 1.85-2.30 (multiplet, 8H, methylene group) 3.35- 3.90 (multiplet, 7H,

[Formula]) 4.0 (double line, 2H, J=6.0Hz

[Formula]) 4.90-5.55 (multiplet, 3H, olefin proton) Example 2 (i) 773 g of acetone was placed in a reaction vessel No. 3 equipped with a reflux condenser, dropping funnel, thermometer, and stirrer.
(13.3 mol) and 7.9 g (0.056 mol) of boron trifluoride diethyl ether complex were added and stirred at room temperature. From the dropping funnel, 310 g (1.11 mol) of the phalnesyl glycidyl ether obtained in (i) of Example 1 was added dropwise. Finish dripping in about 30 minutes. During this time, the reaction mixture gradually generates heat, reaching a maximum temperature of 40°C. After the addition is complete, stirring is continued for another 3 hours. A gas chromatograph of the reaction mixture revealed that phalnesyl glycidyl ether had completely disappeared. 9.3 g (0.111 mol) of sodium bicarbonate is added to the reaction product and heated to recover excess acetone. Next, tap water
Add 620g to neutralize the acid content. After collecting the organic layer by liquid separation, the solvents are distilled off under reduced pressure. The residue was distilled under reduced pressure to obtain a colorless transparent liquid of 4-phalnesiloxymethyl-2,2-dimethyl-1,3.
-170 g of dioxolane were obtained. Yield 45.6%. Boiling point 170-180℃ (0.30mmHg) Elemental analysis C ₂₁ H ₃₆ O ₃ (calculated value) C.74.6% (74.95%); H.10.7% (10.78%) O.14.2% (14.26%) Iodine value 236 (226) IR (cm ^-1 , liquid film) 2975, 2925, 2860, 1670,
1445, 1370, 1290-1170, 1170-1000,
840. ¹ H-NMR (δin ppm, CDCl ₃ , TMS internal standard) 1.35, 1.43 (both singlet, 6H,

[Formula]) 1.60, 1.70 (both singlet, 12H, 4 methyl groups) 1.85~
2.30 (multiplet, 8H, methylene group) 3.35~
4.50 (multiplet, 7H,

[Formula]) 4.90 to 5.55 (multiplet, 3H, olefin proton) (ii) 160 g of the dioxolane compound obtained in Example 2 (i) was placed in a reaction vessel equipped with a reflux condenser, a thermometer, and a stirrer. (0.476 mol), methanol 160g,
4.8 g (0.0476 mol) of concentrated sulfuric acid and 160 g of tap water were added and reacted at 50°C for about 5 hours. After neutralizing the acid content of the reaction product with dilute caustic soda aqueous solution,
Extracted with ether. The ether layer was collected by liquid separation, and the ether was distilled off under reduced pressure. Further, the mixture was dried at 1 mmHg/60 to 80° C. for about 3 hours to obtain 135 g of pale yellow liquid phalnesyl glyceryl ether. Yield 95.7%. of this
The IR and ¹ H-NMR spectra were both consistent with those of phalnesyl glyceryl ether obtained in Example 1. Further, the hydroxyl value (370 [calculated value 379]) and iodine value (257 [calculated value 260]) of this product were similar to those obtained in Example 1. Example 3 Synthesis of phytyl glyceryl ether: (i) Glycidyl etherification was carried out under the same reaction conditions as in (i) of Example 1, except that 1.5 mol of phytol was used in place of farneryl. By distillation under reduced pressure, 474.9 g of colorless transparent liquid phyteyl glycidyl ether was obtained. yield
89.8%. Boiling point 198-200℃ (0.4mmHg) Elemental analysis C ₂₃ H ₄₄ O ₂ (calculated value) C.77.7% (78.35%); H.12.5% (12.58%) O.9.2% (9.07%) Oxirane Oxygen 4.2 % (4.54%) Iodine value 73.4 (72.0) IR (cm ^-1 , liquid film) 3030, 2950, 2925, 2860,
1660, 1450, 1370, 1240, 1160~1000,
900,835 ¹ H-NMR (δin ppm, CDCl ₃ , TMS internal standard) 0.85 (double line, 12H, J = 5.0Hz 4 methyl groups) 1.0-1.70 (broad single line, 19H,
methylene group + methine group) 1.67, 1.73 (both singlet, 3H,

[Formula]) 1.80 to 2.30 (broad multiplet, 2H,

[Formula]) 2.50 to 2.90 (multiplet, 2H,

[Formula]) 3.0 to 3.35 (poly Heavy line, 1H,

[Formula]) 3.40 to 3.90 (multiplet, 2H,

[Formula]) 4.07 (double line, 2H, J=6.0Hz

[Formula]) 5.38 (triple line, 1H, J = 7.0Hz olefin proton) (ii) In (ii) of Example 1, the filtrate obtained in (i) of Example 3 was used instead of falnesyl glycidyl ether. All reactions were carried out under the same reaction conditions except that 0.20 mol of tail glycidyl ether was used. By distillation under reduced pressure, 87.8 g of colorless transparent liquid phyteil glycerol diacetate was obtained. Yield 96.6
%. Boiling point 208-217℃/0.5mmHg Elemental analysis C ₂₇ H ₅₀ O ₅ (calculated value) C.71.7% (71.32%); H.11.2% (11.08%) O.17.2 (17.59%) Saponification value 243.8 ( 246.8) Iodine number 58.6 (55.8) IR (cm ^-1 , liquid film) 3050-2800, 1740, 1440,
1360, 1250 ~ 1180, 1150 ~ 1000. ¹ H-NMR (δin ppm, CDCl ₃ , TMS internal standard) 0.86 (double line, 12H, J = 5.0Hz 4 methyl groups) 1.0 ~ 1.65 (broad single line , 19H,
methylene group + methine group) 1.67, 1.74 (both singlet, 3H,

[Formula]) 1.70 to 2.30 (broad multiplet, 2H,

[Formula]) 2.02, 2.07 (both singlet, 6H, 2 acetyl groups) 3.56 (double, 2H, J = 5.0Hz

[Formula]) 4.03 (double line, 2H, J=6.5Hz

[Formula]) 3.80 to 4.60 (multiplet, 3H,

[Formula]) 5.0 to 5.55 (multiplet, 1H, olefin proton) (iii) In (iii) of Example 1, phyteylglycerol obtained in (ii) of Example 3 was substituted for phalnesylglycerol diacetate. Diacetate 74.2g
Hydrolysis was carried out under similar reaction conditions except that (0.163 mol) was used. Post-treatment was carried out in a conventional manner to obtain 60.4 g of phytyl glyceryl ether. Yield 100%. Elemental analysis C ₂₃ H ₄₆ O ₃ (calculated value) C.74.3% (74.54%); H.12.0% (12.51%) O.12.5 (12.95%) Hydroxyl value 303.7 (302.8) Iodine value 70.6 (68.5) IR (cm ^-1 , liquid film) 3650~3050, 3000~2700,
¹⁶⁶⁰ , 1450, 1365, 1140~850.1H-NMR (δin ppm, _CDCl3 , TMS internal standard) 0.87 (double line, 12H, J=5.0Hz 4 methyl groups) 1.0~1.65 (broad single line , 19H,
methylene group + methine group) 1.67, 1.72 (both singlet, 3H,

[Formula]) 1.80 to 2.30 (broad multiplet, 2H,

[Formula]) 3.34~4.0 (multiplet, 7H,

[Formula]) 4.03 (double line, 2H, J=6.0Hz

[Formula]) 5.37 (triple line, 1H, J=7.0Hz olefin proton) Example 4 The washability (Note 1) of the glyceryl ether of the present invention and a comparative compound were compared by the following method.
The results are shown in Table 2.

[Table] 〓Weight of oil 〓
From the results of this test, the glyceryl ether of the present invention has extremely high cleaning residue compared to conventional glyceryl ether and commonly used moisturizers.
It was found that the build-up was equal to or greater than that of oil, and that it was not easily removed by washing. A hygroscopicity test (Note 2) of the glyceryl ether of the present invention was conducted to evaluate its performance as a humectant.
The results are shown in Table 3.

[Table] 〓Compound weight〓
From the results of this test, it was found that the glyceryl ether of the present invention has higher hygroscopicity even though it appears to have stronger oil properties than conventional glyceryl ethers. Example 6 An emulsification test (Note 3) was conducted on the glyceryl ether of the present invention and a comparative compound to compare their performance as emulsifiers. The results are shown in Table 4.

[Table] From the results of this test, it is clear that among the glyceryl ethers of the present invention, phytyl glyceryl ether having a relatively long alkyl group has a W/O type emulsifying power equivalent to that of known emulsifiers. Ta. Example 7 (Hand cream) An emulsion having the following composition was prepared using Phytail glyceryl ether. Phytail glyceryl ether 5.0 (wt%) Stearic acid 10.0 Stearic acid monoglyceride 1.5 Polyoxyethylene monostearate
1.5 Triethanolamine 0.3 Methylparaben 0.1 Butylparaben 0.1 Fragrance 0.2 Purified water Heat and mix ~ to 70℃, and add ~,
Add the mixture heated to 70°C while stirring to emulsify. Thereafter, the mixture was cooled to 40°C and a white emulsion was obtained. When used on the hands, this emulsion blends well into the skin and does not easily come off when washed, making it suitable as a hand cream. Example 8 (Facial Pack) A mixture having the following composition was prepared using fiber glyceryl ether. Phytail glyceryl ether 2.5 (wt%) Polyvinyl alcohol 15.0 Titanium oxide 5.0 Ethylene glycol 4.0 Methylparaben 0.1 Fragrance 0.2 Purified water Heat the remaining amount to about 90℃, and add little by little while stirring to dissolve uniformly. Then, add ,～,
Stir to homogenize. After cooling to about 40°C, it was added to make it homogeneous. When the resulting mixture was used as a facial pack, it was characterized by moderate stimulation when the film was peeled off from the skin and a long-lasting moisturizing feeling afterwards. Example 9 (W/O cream) An emulsion having the following composition was prepared using Phytail glyceryl ether as an emulsifier. Phytail glyceryl ether 2.0 (wt%) Liquid paraffin 18.0 Isopropyl myristate 10.0 Glycerin 4.0 Propylene glycol 6.0 Sodium benzoate 0.2 Purified water Remaining amount Heat and mix ~ to 75℃, and add ~ to this.
Add the mixture heated to 75°C while stirring to emulsify.
The mixture was cooled to room temperature while stirring to obtain a white emulsion. The obtained emulsion was in the form of a W/O type cream, had good emulsion stability, and had a good feel when used, making it suitable as a cosmetic cream. Example 10 (Lip Cream) A mixture having the following composition was prepared using falnesyl glyceryl ether. Falnesyl glyceryl ether
10.0 (wt%) Liquid paraffin 37.0 Jojoba oil 16.0 Carnauba wax 13.0 Microcrystalline wax 14.0 Vaseline 10.0 Heat and mix each component at 85°C, stir thoroughly to make it homogeneous, then immediately pour into a molding machine and cool.
The resulting mixture was a slightly soft solid with a milky white luster, and when molded into a stick, it blended well and spread well as a lip cream, and was difficult to remove from the lips. Example 11 (lotion) A mixture having the following composition was prepared using phalnesyl glyceryl ether. Falnesyl glyceryl ether
5.0 (wt%) Ethanol 15.0 L-serine 1.0 Sodium pyrrolidone carboxylate 1.0 Polyoxyethylene oleyl ether
1.5 fragrance 0.2 purified water Remaining amount ~ was stirred and mixed to make it homogeneous. The lotion thus obtained blended well into the skin and had a moist feel.

Claims (1)

[Claims] 1 General formula () [In the formula, R is the following formula (m represents an integer from 1 to 10, A and B each represent a hydrogen atom, or both together form a single bond, and when m is 2 or more, A and B are Glyceryl ether of a terpene alcohol represented by ] 2. The glyceryl ether of a terpene alcohol according to claim 1, wherein R in the formula (2) is a falnesyl group. 3. The glyceryl ether of a terpene alcohol according to claim 1, wherein R in the formula () is a phytyl group. 4 General formula () [In the formula, R is the following formula (m represents an integer from 1 to 10, A and B each represent a hydrogen atom, or both together form a single bond, and when m is 2 or more, A and B are A cosmetic comprising a glyceryl ether of a terpene alcohol represented by: