JPS6028945A - Terpene alcohol glyceryl ether and cosmetic containing it - Google Patents

Abstract

NEW MATERIAL:A compound shown by the formula I [R is group shown by the formula II(m is 1-10; A and B are H or linked to form single bond; when m is >=2, A and B may be combination of the above-mentioned two cases)]. EXAMPLE:Farnesylglyceryl ether. USE:Especially useful as a component for cosmetic. Having chemical stability, low irritation to the skin, having surface active properties, useful as an emulsifying agent, oil agent, wetting agent, viscosity builder, etc. PREPARATION:For example, a terpene alcohol shown by the formula ROH is reacted with an epihalohydrin to give a glycidyl ether shown by the formula III, which is reacted with a lower fatty acid anhydride shown by the formula IV(R3 is 1-5C hydrocarbon group) in the presence of a basic catalyst, to give a glycerol diester shown by the formula V. This compound is hydrolyzed in an aqueous solution of an alkali substance such as an alkali metal hydroxide, etc. under heating, to give a high-purity compound shown by the formula I by simple operations in high yield.

Description

DETAILED DESCRIPTION OF THE INVENTION The invention relates to a novel glyceryl ether of terpene alcohol and a cosmetic containing the same.

Conventionally, as α-monoalkylglyceryl ether,
Palmitylglyceryl ether (referred to as chimyl alcohol), stearylglyceryl ether (referred to as batyl alcohol), and oleylglyceryl ether (referred to as serakyl alcohol) present in fish lipids.
4 are known and these are emulsifiers, sometimes W/o
It is known that it has 6i H'Q as an emulsifying anti-41IQ agent, and has 4#18 embedding effect, which is an effect of promoting blood cell production in the bone marrow, anti-inflammatory effect, and anti-tumor activity. Publication No. 49-10724, Publication No. 52-18
No. 171).

However, these known α-monoalkylglyceryl ethers have the drawbacks of being solids with a low melting point and being irritating to the skin.

Investigations have also been made to improve the shortcomings of Kosai et al. was proposed (Japanese Unexamined Patent Publication No. 52-12
No. 109). However, although this product solved the above-mentioned drawbacks to some extent, it also had new drawbacks such as decreased hydrophilicity and poor emulsion stability.

Therefore, the present inventors conducted research to overcome the above-mentioned drawbacks of the known α-monoalkylglyceryl ethers, and found that they are compatible at room temperature, chemically stable, have excellent emulsion stability, and As an α-monoalkylglyceryl ether that does not irritate the skin, α-mono(methyl-branched alkyl)glyceryl ether represented by formula (II) having a methyl branch in the main chain was proposed (Japanese Patent Publication No. 36260/1983).

(In the formula, m is an integer from 2 to 14, n is 3/, c to 1
However, the above α-mono(methyl branched alkyl) glyceryl ether (It) is an integer having a methyl branch near the center of the alkyl main chain. Since it is a complex mixture containing stearyl glyceryl ether as the main Tri component (containing 75% fJ), if the composition of the alkyl group changes, there is a risk that the desired performance or physical properties will not be obtained. It had the disadvantage that managing the current level of personnel at the time was difficult.

(On the other hand, in the natural world, there are a wide variety of polyprenyl compounds (terpene compounds) that are made by repeating isoprene units as compounds that have multiple methyl branches (maintaining a regular positional relationship) in the alkyl main chain. It is well known that borylnyl compounds are widely used in the fields of fragrances, industrial chemicals, products, cosmetics, foods, etc.In recent years, polyprenyl compounds have been used in the production of hair. It was discovered in the narrow path 7 no.
No., JP-A No. 57-19234+, No. 57-19234
No. 2, No. 57-192341, No. 57-192340
No. 57-192339, No. 57-106618, No. 54 89035, No. 54-5043, No. 53
-Temple No. 96330).

Under these circumstances, the present inventors conducted intensive research on the surface chemistry of the above-mentioned borylnyl compound, particularly on the Am content of the emulsifier, and found that glyceryl ether derived from a specific terpene alcohol or conventional α-monoanone They found that it has vague properties not found in killglyceryl ether and is useful as a cosmetic ingredient.The present invention was thus completed.

Therefore, the present invention provides the following general formula (1) [In the formula, R is the following formula CH.

B (m is 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 glyceryl ether of a terpene alcohol represented by the following formula (which may be a combination of the above two cases) and a cosmetic containing the glyceryl ether.

Conventionally, glyceryl ethers that are extracted from terpene alcohols include IJ) q cyclic molderpe/alcohol glyceryl ether (Nishia Machikan @ No. 711916)
, Shichino and Shifitanyl glyceryl ether (6-0
-C3', 7', + +', +5'-detramethylbexadecyl]glycerol and H2.3-c-o-[
5', 7', Il', I5'-tetramethylhexadenyl]glycerol) (BiOC11 River 1.
'+'Lry+4th Lane, pp. 1595-1599 (196
5 years); Journal of Lipid Re5e
arC11+ (Volume 19, 782.788 Tei 1', '6
8th grade)) I know 7 households.

Shikijina IJ) et al., the glyceryl ether of the terpene alcohol of the present invention differs from the above-mentioned public FJ-added 'nose' and has a #r normalized @I-nose, which is not described in the χ reference. .

Glyceryl ether of terpene alcohol of the present invention (1
), the J building is constructed by the following method, for example.

Method A Niluiz acid (v) H0H (1) Method B: Base (R3Co)20 (IV)---->ROCH2C)1-OH20CO
R3 ('Mochi Tsumugi Showa 57-16061) 0COR.

(vl) (1) (In the formula, R1 is a hydrogen atom or a hydrocarbon group, R2 is a hydrocarbon group, R3 is a hydrocarbon group having 1 to 5 carbon atoms, X is a halogen cloth, and R is the same as above. Same thing f!: 11 し1-) In the example of the present invention, F! Method B is preferably used when producing glyceryl ethers of terpene alcohols containing 14'II bonds with a value of 11ω (for example, farneol). In other words, method A uses glycysol ether (
1v) in the presence of a Lewis acid catalyst to give 1,6-dioxolane (V), which was then hydrolyzed in an acidic water bath to give glyceryl ether (1
). However, since this method involves two steps of reaction under acidic conditions, isomerization, rearrangement, and polymerization of unsaturated bonds by acid catalysts occur simultaneously, resulting in glyceryl ether (1
) may lower l[A. On the other hand, method B requires a simple operation of +tli, with still pure glyceryl ether (1
) can be obtained in high yield.

Method B will be explained in detail below.

First, glycisol ether (B) is produced by Williamson type ether synthesis with terpene alcohol (Ill) tobihalohydrin. The output terpene alcohol has the following formula (III) CH.

A (wherein A, B and m are the same as above), and an industrially easily available one is phytol [
H-(CH2CH2CH2CH2) -CH2C=CH
2CH20H]3 etc. are exemplified.

This ether synthesis reaction is carried out by a method known per se using a phase transfer catalyst. 1. In a 60-60% aqueous solution of an alkaline substance such as an alkali metal hydroxide, a terpene alcohol ( III) React with epichlorohydrin (preferably epichlorohydrin). The charge of the alkaline substance (ill) is 1 to 10 mol per 1 mol, preferably 6 to 6 mol, and the quaternary onium salt is 0.01 to 0.20 mol. 1 to 10 moles, preferably 2 to 4 moles of shrimp halohydrin.

The reaction temperature is 60 to 80°C, preferably 45 to 60°C, and the reaction medium may not be used, but inviscid hexane,
Heptane, benzene, toluene, xylene, etc.) hydrocarbons, ether, tetrahydrofuran (THF),
Ethers such as diglyme and dioxane can also be used. When doing this, glycidyl ether (
1v) is obtained in a yield of 80-85% (based on lli).

To obtain glycerol diester (vI) from glycidyl ether (IV), in the presence of a basic catalyst, (IV)
is reacted with lower fatty acid anhydride. Examples of the basic catalyst include tertiary amines such as triethylamine, trinolobylamine, triethylamine, trioctylamine, pyridine, dimethylaniline, quinoline, and tetramethyl-1,6-diamithexane. Examples of the lower fat tzr* anhydride include vinegar anhydride, propionic anhydride, and anhydride, with acetic anhydride being particularly preferred. The reaction is carried out with respect to 1 mole of glycidyl ether (IV), 1 to 60 moles of acid anhydride, preferably 1 to 15 moles, and 0.01 to 0.20 mole of Hanawa group catalyst, preferably 0.
05 to 0.10 mol was used for one cycle, and the reaction temperature was 70 to 150 mol.
°C1 Preferably 80 to 120"C. No solvent is required, but an inert solvent can be used if necessary. In this way, glycerol diester (VI) is IV) with a yield of 90-95%.

Hydrolysis of the glycerol diester (% II) is carried out by methods known per se. That is, (vl) 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 enemy of alkalinity is not particularly limited to III, but CVI) 2 to 1 mole.
More than 1 mol, preferably 2 to 5 mol, is used. Although the reaction proceeds in an aqueous solution, water bath solvents such as lower alcohols such as methanol, ethanol, and isopropanol, and ethers such as 'I'HF' and dioxa? It gives good results when heated and refluxed at 50-100'C. When doing so, the desired glyceryl ether (1) is obtained in constant yield.

The glyceryl ether (1) of the present invention has no decomposable bond such as an ester group in its molecular structure, so it is chemically stable, causes little skin irritation, and has a chemically stable bond that does not irritate the skin. 1 emulsifier, +11 for having the i-th order [
]ql+ (emollient), moisturizing agent, thickener, etc., and is particularly useful as a component of cosmetics.

The properties of typical compounds of the present invention are as follows.

Table 1: Glyceryl ether The glyceryl ether of the present invention has polar groups such as hydroxyl groups, so it is hydrophilic and hygroscopic. Compared to ether, the number of methyl branches in the alkyl chain moiety is larger and it also has double bonds, which hinders the alignment of molecules in aqueous solutions, resulting in the formation of liquid crystals and other liquid crystals. As a result, it is difficult to dissolve in water, and its characteristics as an older brother Tsuchiura have become stronger. Therefore, when the compound of the present invention is blended into a cosmetic and applied to the skin, it has a strong resistance to washing and a high persistence on the skin, that is, it has a long lasting effect as a cosmetic.
The characteristic of "i" is expressed. 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 phyteil deliceryl ether, are used as water-in-oil type surfactants as lipophilic surfactants.

The proportion of the glyceryl ether of the present invention in cosmetics may vary depending on individual factors, but when used as an emulsifier, it is 0.2 to 1511%, and when used as an oil or moisturizer, it is 2 to 5 outi, i. % is appropriate.

Further explanation will be given below using actual guns, but the present invention is not limited to these actual guns 1+111C.

Synthesis of real mPJ1 farnesyl glyceryl ether
: (1) Into a 31 reaction vessel equipped with a reflux condenser, a dropping funnel, a thermometer, and a stirrer, 31! SOy (180% as sodium hydroxide)
9 [: 4.5 mol]), farnesol 333.6
．． 9 (1.5 mol) and Hexa 75409 and stir vigorously. Then, 50% tetrazotylammonium hydrogen sulfate 50.9, @ (25% as hydrogen sulfate)
59 [: 0.075 mol]) is added. Keep the temperature of the reaction mixture at room temperature and pour it into the dropping funnel.
FU y277.51/ (5,0 mol) Wol'J30
Drip in minutes. During this time, the reaction mixture becomes similarly exothermic. After the imitation is completed, the temperature of the reaction mixture is set to 50~55'OK.
Keep stirring for about 3 hours. Gas chromatography confirmed that farnesol had been used. To the reaction product, tap water 6 70
Add g and stir. The hexane layer is then collected by fraction. Reduce pressure [hexane is distilled off, and the residue is subjected to pressure distillation. 352 g of colorless and transparent farnesyl glycidyl ether was administered. Yield 84%.

Boiling point 155-160℃ 10.6 Hg elemental fraction rC0
As (it −1 1m)C.8H3oO2. 7
Section 7, 6 (77, 65%); H. 10.6chi (1
0.86%) 0.11.7% (I L49 oxiranic acid * 5.62% < 5.70% iodine 1
Song 273 (273.6) IR (Cm-”, film formation) 3060. 2975, 2
930, 2860.

1670, +445. 1375.　1250.

1160~1υ4υ, 1υ (for ~9υ0.

865.

”H-NMR(δin ppm1CD(J3,'l'M
s internal standard) 1, 60, L70. 1.75 (both 1ton line, +2H, 4 methyl groups) L85-2.60
<Multiple ugliness, 8H. methylene group) 2.40-2.9L]
(Multiple 3, 35 ~ 3.80 C child ME m, 2H
, n) (1) Add 102.9 (1.0 mol) of acetic anhydride and triethylamine heavy bond to the reaction vessel of 1) equipped with a reflux condenser, dropping funnel, temperature side, and stirrer, and heat for 90 minutes while stirring. Warm to U. Then,
Alnesyl glycidyl ether 55.7, S' (0.2 mol) prepared in (1) of Example 1 was added dropwise from the dropping funnel over 40 minutes. During this period, heat the reaction mixture as appropriate to bring the temperature of the reaction mixture to 90~+00''O.
Keep it. After the dropwise addition of glycidyl ether was completed, the reaction was continued at 120°C for another 4 hours. From the gas chromatograph of the reaction mixture, glycidyl ether was observed to have a photototal VC.
．． It was confirmed that it had disappeared. Then, excess acetic anhydride was distilled off from the reaction mixture under reduced pressure -f-6. Then, dilute hydrochloric acid is added to mix triethylamine into the medium. After extracting various substances using the ether extraction button, the ether is distilled off. The residue is then subjected to vacuum distillation. Black transparent single generation σ
) 75.6 g of farnane glycerol diacetate was obtained as a product. Yield 99.5%.

Boiling point 195-199℃ (0.6min Hg) Elemental analysis C'22"':! As 605 (31 last Ift!
) C, 69,2% (69,5%); H, 9,80
% (9,50%), 0, 20.7% (2L1%) Ri/chemical 1 song 297 (295) Iodine 1 song 207 (200) xR (cm-”, v&pA) 2970.2925
．． 2855.1740 (C-0), 16611. +
440.1565°1220, 1160~10 (Jo,
855IHHλ4R(δin ppm, CD(J3
,'rMEI internal tm*>1.60. +, 6B, C
75 (both -t1t[j, +2H14 methyl group)C
8ri ~ 2.20 (multiple line, 14H, methylene group ← 2 digits σ) COO view, ) 3.50 (2m line, 2H, J=
5. OHzi@, 6H, -CH20CH2C and 0Ac
Cdan 20Ac) 4.90~5.50 (Multiple line, 3H
, olefin protons) (lit) Into a +1I reaction vessel equipped with a reflux condenser, dropping funnel, temperature needle, and stirrer, 64.9 g of 60% sodium hydroxide water (mY and 64.9 g as sodium hydroxide) was added.
5.9 [0,487 mol]), 200 ml in x-1/-
) and stir. Then, from the dropping funnel, add 1
61.7 g (0,162 mol) of tafarnesylglycerol diacetate obtained from (It) was added dropwise over about 20 minutes. The reaction mixture is then heated to reflux (6 hours) at 80'CK. The reaction raw FM, '$lJ, becomes a homogeneous transparent solution. After cooling, tap water 200.1 ether 5
00#1 Atc and subjected to ether extraction. An ether layer is obtained by synthesis. The ether was distilled off under reduced pressure, and further 1
Dry at 60 to 80°C (3 hours) at am Hg K to obtain farnesyl glyceryl ether 47, a colorless and transparent liquid.
．． I prayed for 9. j1M rate 97.9%.

Elemental analysis as 01111H3203 (calculated value) C,
76.2% (72.93%); H, N, 0 section (10
, 88chi) 0, 16.5% (16,19%) Water iv, 1 group 672.8 < 378.5) 1 iodine 254 (256,8) hR (c, n-', 76 membrane) 665 (J ~310
0.2975.2925°2860.1660. +44
0.1370.1100°1080~1000.820"H-NMR (δin ppm, CD (J3,
TMS internal standard) 1.67, 1.70.1.75 (both 11 lines, 12H14 methyl groups) 1.85-2
．． 30 (multiplet, 8H, methylene group) 3. ．． 55~
3.90 (multiple line 4.90~5.55 (multiple line, 3H
, olefin proton) Practical fee 2 (1) Reflux? Kiyuki device, dropping funnel, prefecture chant, stirrer υ
Add acetone 773 # (13
, 3 mol), boron trifluoride zoether ether complex 7.
Add 9.9 (0,056 mol) and stir at ￥ temperature.
i+Jk'r+kl-nQ1mtt&l11θMll'
F (Jil?-7Ryo/Rennenluglycisol ether 31
0.9 (,1,+1 mol) is added dropwise. The dripping is completed in about 30 minutes. During this time, the reaction mixture gradually became exothermic, and H,
4 m degrees is 40'C.

After finishing the process, Sarakan continues stirring for 3 hours.

Gas chromatography of the reaction mixture revealed that farnesyl glycidyl ether had disappeared from the entire body.

Vertical hydrogen carbonate in the reaction product) +7um9,! 5'(0
, 111 mol) and the hO and excess acetone are recovered. Next, 620 g of tap water was added to neutralize the acid content. The organic layer is removed by classification, and the solvent is distilled off under reduced pressure. The residue was evaporated under reduced pressure, and 170 I of 4-farnesyloxymethane-2,2-dimethyl-1,6-dioxolane was added to the colorless and transparent residue. Yield: 45.6 cm.

Boiling point 170-180"'C (0,30 chuu Hg) Elemental analysis As C21H3603 (gj calculation 111) C,7
4,6% (74,95 section): H,10,7% (10
, 78 section) 0, +4.2% (14,26%) 1 Yo-kei song 236 (226) IR (Cnl-', /&ll6a) 2975+
2925121:t61], +67011445. 1
370. 1290~N70°1170~1000.
84 [).

"H-NMR (δin ppm, CD (J3+T
MS inside rj++ 46 m) 1.35.1.4'S
(both 17Jj line, (5H1 east line, '12H, 4 methyl groups > 1.85-2.30 (multiple line, 8H, methylene 4) 6.65-4.50 (multi-lane, 7H).

(11) Refluxing G, (14 degrees weighing 2g of stirring)
In a reaction vessel of No. 1, diogisolan compound 1601 (0,476 mol) prepared in (1) of Example 2 and methanol 16
[]]y, - Choshun 4.8.9 (0,0476 mol),
Tap water +60. V was added thereto, and the reaction was allowed to proceed at 50"C for about 5 hours. The acid content of the reaction product was neutralized with dilute aqueous sodium hydroxide solution, and then extracted with ether. The ether layer was collected during the synthesis, and the ether layer was extracted with ether under reduced pressure. was removed.

The dried material was dried at 1 Hg/60 to 80° C. for about 6 hours to obtain farnesyl glyceryl ether 13511, which had a light brown color and a peach shape. Yield 95.7%. The IRl”H-NMR spectrum of this product is a co-trap real image l+111
One piece of farnesyl glyceryl ether obtained in . In addition, the hydroxyl group 1lIle (370 [
gtA11379]), iodine value (257[,1
j1-1 direct 260] was the same direct as that of the barrel in Example 1. In addition to using 1.5 moles of phytol instead of Falui and Lille,
All glycidyl etherifications were carried out under the same reaction conditions.

Under the influence of Lee Linbo, I received 474.9.9 of a colorless and transparent liquid, Fiteil Glycidyl Ether. Yield 8ν, 8%.

Boiling point 198-200℃ (0.4am Hg) Elemental force/analysis ``23H4402 (Ba [R, region) C, 77
, 7th section (78, 35th section); H, 12,5% (12,
Section 58) 0, 9.2% (Section 9,07) Oxirane e accumulation Section 4.2 (4,54%) Iodine 1 piece
73.4 (72,0) IR (cM+-”, /& model) Roo6o, 29
50.2925.2a6o.

+660.1450.1370, 1240°1160~
1000.900,835"H-NMR (δin ppm, CDC73, TM
8 internal standard) 0.85 (double, taku, I 2 H, J
=5. θHz4 methyl groups) 1.0 to 1.7 [J
(Broad single line, 19H,;
3%JH2) 6.40~3.90 ('k jjL
@12H, -CH2QC and CHCH2) 4.0
7 (Double line, ゝn' 5.38 (3ffi line, l H, J = 7.0 Hz olefin proton) (Ill real M if! I 3 in place of farnesyl glycidyl ether at (I+) of real m1HJ1 (1) of 0.20% glycidyl ether
The seagull using Mol was reacted with the male under the same reaction conditions. By distillation under reduced pressure, 87.8 g of colorless transparent liquid phytyl glycerol diacetate was obtained. Yield 96.6
%.

dI point 208-217℃ 10.5 degrees Hg elemental analysis C
As 27H5005 (total Uili) C, 71, Aphrodisiac (7
L62%) ; H, N, 2% (11,08%) 0,
+7.2% (17,59%) 1 saponification 243.8 (246,8) 1 iodine
58.6 (55,8) IR (LJn'', l'i membrane) 3050~28[J
LJ, +740.144tJ.

1360, 1250~118υ, N5o~1000゜"H-NMR (δin ppm, CDC73, TM
S internal standard 11/= )0.86 (double line, l 2 H
, J=5-OHz 4-methyl methyl group) 1.0-1.65
(Prodna single-a, l 9 H, methylene group + methine 4) 1.67, 1.74 (Both one claw wire, 3H.

(Broad multiplet, 2H.

(both with Ikkyo, 6H12 pieces of acetyl 4) 7), 56
(2am, 2H, J=5.0 HzAc0Ac ~5.55 (polysalt-1iH, olefin/f mouth)?) 1ii) In (ili) of Implementing Country 1, 14 M It instead of farnesylglycerol diacetate !
The hydrolysis was carried out under the same reaction conditions, except that 74.2 g (0,165 mol) of 11-dihydryl glycerol diacetate was used in (11) of 13. The post-treatment was strengthened by a conventional method to obtain Phytail Glyceryl Ether 60.4.
9 +'J.

Yield: 100 cm.

Elemental analysis as C23H4603 (calculated value) C,74
,3% (74,54%): H,12,0π12.5
1%) 0,12.5 ratio (12,95%) Hydroxyl value 305.7 (302,8) Iodine value 70
．． 6(68,5) IR((:In-”, gII!II) 3650~3
050.3 (700-2700°1660, 1450.
1365.1140~850°1H-NMR (δin ppm, CD(43, TM
8 internal + tJA4) 0.87 (double line, i 2H, J
-5, OHzd methyl group) 1.0 to 1.65 (pro F single line, l 9 H, methylene group 10 methine group)
1.67, 1.72 (both in a straight line, 5H.

(Broad multiplet, 2H1 4, os C2JrL=, 2H, J=6.0 Hz Actual Example 4 The glyceryl ether washable #I property (Note 1) of the present invention was compared using the following σ) method VC.

The results are shown in Table 2.

Table 2 (Note 1) Washability: 2.5 cm x 5.5 a
120 ± 2 da of the test compound was uniformly applied to a glass plate using chloroform, and the mixture was heated at 60°C for 21°C.
immersed in a 0.5% aqueous solution of sodium lauryl fA acid, and in this water f# liquid iI! Insert a propeller with a diameter of 5 cIn.
L. ．． Stirred at 300 rpm for 2 minutes. Next, this glass plate was placed in water at 60° C. and 21° C. and stirred with the above-mentioned propeller at 30 rpm for 1 minute for rinsing. After drying, the weight of the glass plate was measured, an electric weight was added, and the cleaning residue was calculated from the following formula.

The results of this test show that the glyceryl ether of the present invention has extremely high cleaning residual properties (compared to conventional glyceryl ethers and commonly used moisturizers, etc.), and shows performance equivalent to or better than oil agents. It became clear that it was not easily removed.

A hygroscopicity test (Note 2) of the glyceryl ether of the present invention was conducted to evaluate its properties as a humectant.

the result? It is shown in Table 6.

Table 6 (Note 2) If 2. Ocm x 2. O
The test compound was placed in a cylindrical glass container of 1.00.9 υ) and dried, and the humidity was 93% and the temperature was maintained at constant humidity and temperature of 25'°C. Add,
1 hygroscopicity was calculated from the following formula.

From the results of this trial run, it was found that the glyceryl ether of the present invention has higher hygroscopicity, despite having stronger apparent oil properties than conventional glyceryl ethers.

Practical 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 4 (Note 6) Emulsification test: Mix 5 g of liquid paraffin 451L Gifu compound v, 75'T,! heated to. Purified water 50)? 75'C! Heat to
, s paraffin and the test compound to emulsify it, and the mixture was cooled to room temperature while stirring. Immediately after observing the emulsified cotton, it was further heated to 25'C! The axis of separation after storage for 7 days was observed, and the emulsion stability was calculated using the following formula.

The results of this test revealed that among the glyceryl ethers of the present invention, the phyteyl glyceryl ether having a relatively long alkyl group has WlO type emulsifying power equivalent to that of known emulsifiers.

Practical IM Example 1 (Hand Cream) An emulsion having the following group 5y was prepared using Phytail glyceryl ether.

■ Fiteil glyceryl ether 5.0 (, dt
itl season ■ Stearic acid 10.0 ■ Stearin-related monoglyceride 1.5 ■ Polyoxyethylene monostearate 1.5 ■ Triethanolamine 0.6 ■ Methylparaben 0.1 ■ Butylparaben 0.1 ■ Fragrance 0.2 ■ Purification Heat and mix the remaining amounts of water ■~■ to 70°C, and add the mixture heated to 70°C from ■~ (by force, ■) under stirring to emulsify. Then, cool to 40°C and add 8). It's a white emulsion. When this emulsion was used on the hands, it blended well into the skin, and when the hands were washed, it increased in texture as a hand cream.

A mixture * having the following composition was prepared using Mitsu MM8 (, yEcial Pack) Fuiteil glyceryl ether.

■Fytail glyceryl ether 2, 5 (JT
L 44) ■ Bonyvinyl alcohol 15.0 ■ Teta oxide 15.0 ■ Ethylene glycol 4.0 ■ Methyl paraben 0.1 (0 Fragrance 0.2 ■ Purified water Heat the remaining amount ■ to +li'J90"°C. , (to W stirring F (2)
Add it little by little to make it uniformly thick. Next, (1), (3
) to () and stir to make it homogeneous. After cooling to about 40"0, add (,0) to make it homogeneous. When the mixture is used as a facial pack, it will leave a film on the skin.
It was characterized by moderate irritation when exfoliated and a long-lasting moist feeling after exfoliation.

Actual weaving example 9 (W10 cream) Using fiber glyceryl ether as an emulsifier,
1.14 emulsions having the following composition were prepared.

■ Fiteil glyceryl ether 2,0 (ff
i, #t%) ■ Liquid paraphyte 7 18.0 ■ Myristicin + jl- (soprovir 10.0 ■ Glycerin 4.0 ■ Propylene glycol 6.0 ■ Female, sodium chloride 0.2 ■ 4N hard water residual liquid ■ ~ Mix and heat to 75"C, and add 75" of
The mixture heated to 0.degree. C. is emulsified under stirring. The mixture was cooled to room temperature while stirring to obtain a white emulsion.

The resulting emulsion was in the form of a W2O type paste, had good emulsion stability, had a good feeling of use, and was suitable as a cosmetic cream.

Confirmed Example 10 (Lip Balm) A mixture having the following composition was prepared using farnesyl glyceryl ether.

■ Farnesyl glyceryl ether 10.0 (4 times) ■ Liquid paraffin 67.0 ■ Jojoba oil 16.0 ■ Carnauba wax 15.0 ■ Microcrystalline wax +4.0 ■ Vaseline 10.0 Heat and mix each component at 85℃ After stirring the liquid to make it homogeneous, it is immediately poured into a molding machine and cooled.

The desired mixture was a slightly chewy solid with a milky white gloss, and when molded into a stick, it blended easily and spread well as a lip balm, and also had the property of being difficult to remove from the lips.

Confirmed example 11 (lotion) Using farnesyl glyceryl ether, the following set tr
A mixture with z was prepared.

■ Fanesylglyceryl ether 5.0 (weight 1) (li) Ethanol 15.0 ■ L-serine 1.0 ■ Sodium pyrrolidone carboxylate 1.0 ■ Polyoxyethylene oleyl ether 1.5 ■ Fragrance
0.2 (1) Purified water The remaining amounts (2) to (2) were stirred and mixed and homogenized. The lotion prepared in this way blends well into the skin and has a moist feel.

Margin below

Claims (1)

[Scope of Claims] 1. General formula (1) [wherein R represents the following formula H3 (m represents an integer from 1 to 1D, 8 and B each represent a hydrogen atom, and 〜・(M111I) Let the m car join together to form a single bond, and the m car 2
In the case of the main character, A and B (Ma @ II El self in the case of two σ
) A terpene alcohol ether represented by [showing a group represented by i] which may be sweetened. 2. The glyceryl ether of a terpene alcohol according to claim 1, wherein R in the formula (1) is a farnesyl group. 5. The glyceryl ether of a terpene alcohol according to claim 1, wherein R in the formula (I) is a phytyl group. 4. General formula (1) [wherein R is the following formula H3 B (m is an integer from 1 to 10, A and B each represent a hydrogen atom, or both form a single bond together) and when m is 2 or more, 8 and B may be a combination of the above two cases. Cosmetics with special characteristics.