2,3-Dialkoxypropyl glyceryl ether and its preparation process as well as cosmetic composition containing same

Disclosed herein is a novel 2,3-dialkoxypropyl glyceryl ether and the preparation process for it. The above diglycerin dialkyl ether is readily prepared with high yield and purity by reacting its corresponding glycidyl ether with a protected glycerin to form a 1,3-dioxolan compound, followed by etherifying the thus formed 1,3-dioxolan compound into a dialkyl ether dioxolan compound, and then hydrolyzing the resultant dialkyl ether dioxolan compound. This diglycerin dialkyl ether is useful as an emulsifier, cleaner etc., and is preferably used as a component of cosmetic compositions. A cosmetic composition comprising the above 2,3-dialkoxypropyl glyceryl ether is also disclosed.

BACKGROUND OF THE INVENTION 
1. Field of the Invention 
This invention relates to a novel 2,3-dialkoxypropyl glyceryl ether 
(hereinafter may be abbreviated as "diglycerin dialkyl ether") and its 
preparation process as well as a cosmetic composition containing same. 
2. Description of the Prior Art 
A number of polyalcohol derivatives containing one or more ether bonds 
therein are present in the nature. Among such polyalcohol derivatives, 
monoalkyl ethers of glycerin (called "glyceryl ethers") are particularly 
well-known. For example, fish lipids contain palmityl glyceryl ether 
(called "chimyl alcohol"), stearyl glyceryl ether (batyl alcohol) and 
oleyl glyceryl ether (selachyl alcohol). 
These glyceryl ethers have found wide-spread commercial utility as base 
materials for cosmetic compositions, making use of their w/o 
emulsification characteristics (Japanese Patent Laid-open Nos. 87612/1974, 
92239/1974, and 12109/1977, etc.). Besides, they are also known to have 
physiological activities such as erythropoietic stimmulating effect for 
bone marrow, anti-inflammatory effect and anti-tumor effect (Japanese 
Patent Publication Nos. 10724/1974 and 18171/1977). 
Taking a hint from the fact that such glyceryl ethers are unique 
surfactants having numerous characteristic features, it has been attempted 
to derive from polyhydric alcohols polyol ether compounds having a 
molecular structure similar to these glyceryl ethers (in other words, 
containing one or more ether bonds and hydrophilic OH-groups within their 
molecules)--U.S. Pat. No. 2,258,892, Japanese Patent Publication No. 
18170/1977, Japanese Patent Laid-open Nos. 137905/1978 and 145224/1979, 
etc. The thus-obtained polyol ether compounds are utilized as base 
materials for cosmetic compositions owing to their w/o emulsification 
characteristics (German Offenlegungsschrift No. 2,455,287) and, besides as 
general emulsifiers, antimicrobial and fungicidal agents. 
SUMMARY OF THE INVENTION 
An object of this invention is to provide a novel and useful polyol ether. 
This object is achieved by a diglycerin dialkyl ether represented by the 
general formula (I): 
##STR1## 
wherein R denotes a saturated or unsaturated, straight chain or branched, 
aliphatic hydrocarbon group containing 8-24 carbon atoms, and R' means a 
saturated or unsaturated, straight chain or branched, aliphatic 
hydrocarbon group containing 1-24 carbon atoms. 
The novel diglycerin dialkyl ether according to this invention, which ether 
is represented by the general formula (I), is readily prepared with high 
yield and purity from its corresponding glycidyl ether having the general 
formula (V): 
##STR2## 
wherein R is a saturated or unsaturated, straight chain or branched, 
aliphatic hydrocarbon group containing 8-24 carbon atoms. The glycidyl 
ether of the general formula (V) can in turn be prepared easily from its 
corresponding alcohol. 
For example, an intended diglycerin dialkyl ether of the general formula 
(I) may be prepared by reacting its corresponding glycidyl ether of the 
formula (V) with a glycerin (VI) whose 2,3-hydroxyl groups are protected 
by a suitable protecting group, i.e., an acetal or ketal of glycerin 
(hereinafter referred to as "protected glycerin") to form a 1,3-dioxolan 
compound (II), etherifying the thus-formed 1,3-dioxolan compound (II) into 
a dialkyl ether dioxolan compound (IV), and then hydrolyzing the resultant 
dialkyl ether dioxolan compound (IV). The above reactions are represented 
by the following reaction formulae: 
##STR3## 
wherein R, R', R.sub.1 and R.sub.2 have the same significance as defined 
above. 
The diglycerin dialkyl ether (I) according to this invention is chemically 
stable, develops little irritation to skin and pertains surface activity. 
Accordingly, it is useful as an emulsifier, cleaner, oil (emollient), 
self-emulsifying oil, wetting agent and thickener. It is preferably used, 
principally, as a component of cosmetic compositions. 
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT 
The alkyl glycidyl ether (V) used as a starting material in the preparation 
process of this invention contains a saturated or unsaturated, straight 
chain or branched, aliphatic hydrocarbon group containing 8-24, and 
preferably 8-20 carbon atoms. As specific examples of such alkyl glycidyl 
ether (V), may be mentioned straight chain, primary alkyl glycidyl ethers 
such as n-octyl glycidyl ether, n-decyl glycidyl ether, n-dodecyl glycidyl 
ether, n-tetradecyl glycidyl ether, n-hexadecyl glycidyl ether, 
n-octadecyl glycidyl ether, n-octadecenyl glycidyl ether (oleyl glycidyl 
ether) and docosyl glycidyl ether; branched, primary alkyl glycidyl ethers 
such as 2-ethylhexyl glycidyl ether, 2-hexyldecyl glycidyl ether, 
2-octyldodecyl glycidyl ether, 2-heptylundecyl glycidyl ether, 
2-(1,3,3-trimethylbutyl)octyl glycidyl ether, 2-decyltetradecyl glycidyl 
ether, 2-dodecylhexadecyl glycidyl ether, 2-tetradecyl-octadecyl glycidyl 
ether, 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)octyl glycidyl ether and a 
methyl-branched isostearyl glycidyl ether represented by the following 
formula: 
##STR4## 
wherein m stands for integers ranging from 4 to 10, n means integers 
ranging from 5 to 11, m+n ranges from 11 to 17, and the methyl-branched 
isostearyl glycidyl ether has a distribution with a peak at m=7 and n=8; 
secondary alkyl glycidyl ethers such as sec-decyl glycidyl ether, 
sec-octyl glycidyl ether and sec-dodecyl glycidyl ether; and tertiary 
alkyl glycidyl ethers such as t-octyl glycidyl ether, and t-dodecyl 
glycidyl ether. 
Incidentally, certain processes have recently been developed to prepare 
alkyl glycidyl ethers from their corresponding alcohols (ROH) with high 
yield without need for isolating their corresponding halohydrin ethers 
(see, for example, Japanese Patent Laid-open Nos. 76508/1979, 141708/1979, 
141709/1979 and 141710/1979). 
On the other hand, as the protected glycerine (VI), there are acetals of 
glycerin, which acetals are derived from aldehydes and ketals of glycerin 
which ketals are derived from ketones. As specific examples of compounds 
to be employed to form protecting groups, namely, aldehydes for converting 
glycerin into acetals, there may be mentioned aliphatic aldehydes 
(formaldehyde, acetaldehyde, propionaldehyde, octylaldehyde, etc.), 
alicyclic aldehydes (cyclopentylaldehyde, cyclohexylaldehyde, and the 
like), and aromatic aldehydes (benzaldehyde, naphthylaldehyde, etc.). On 
the other hand, exemplary ketones to obtain ketals may include aliphatic 
ketones (acetone, methyl ethyl ketone, diethyl ketone, methyl propyl 
ketone, dipropyl ketone, ethyl propyl ketone, methyl hexyl ketone, and the 
like), alicyclic ketones (cyclobutanone, cyclopentanone, cyclohexanone, 
cyclooctanone, etc.) and aromatic ketones (acetophenone, benzophenone, 
etc.). The preparation of protected glycerins from these compounds and 
glycerine can be carried out by subjecting glycerin and the above ketones 
or aldehydes to a dehydration/condensation reaction in the presence of an 
acidic catalyst in a manner known per se in the art. 
As exemplary catalysts usable for the reaction between the alkyl glycidyl 
ether (V) and protected glycerin (VI), may be mentioned basic catalysts 
such as alkali metal hydroxides (for example, LiOH, NaOH, KOH, etc.), 
alkali metal alcoholates (for instance, NaOMe, NaOEt, t-BuOK and the 
like), tertiary amines (for example, triethylamine, tributylamine, 
tetramethyl ethylenediamine, tetramethyl-1,3-diaminopropane, 
tetramethyl-1,6-diaminohexane, triethylenediamine, etc.); and acidic 
catalysts including protonic acids such as sulfuric acid, hydrochloric 
acid, nitric acid, phosphoric acid and the like as well as Lewis acids 
such as boron trifluoride-ether complex, boron trifluoride-acetic acid 
complex, boron trifluoride-phenol complex, aluminum chloride, aluminum 
bromide, zinc chloride, tin tetrachloride, antimony chloride, titanium 
tetrachloride, silicon tetrachloride, ferric chloride, ferric bromide, 
cobaltic chloride, cobaltic bromide, zirconium chloride, boron oxide, 
activated acidic alumina, etc. 
The above reaction is generally carried out by reacting an alkyl glycidyl 
ether (V) with a protected glycerin (VI) in a ratio of 1 mole to 1-10 
moles, and preferably 1-5 moles in the presence of 0.001-0.02 mole, and 
particularly preferably 0.01-0.1 mole of a catalyst and at 
70.degree.-150.degree. C., and particularly preferably 
90.degree.-120.degree. C. 
The protected glycerin (VI) may be used, theoretically speaking, in an 
equimolar amount with the alkyl glycidyl ether (V). Practically speaking, 
it is desirous to use the protected glycerin (VI) somewhat more than the 
equimolar amount for better yield and shorter reaction time. Although the 
reaction may still proceed without any reaction solvent, it is most 
appropriate to use the protected glycerin in an excess amount so that it 
can also serve as a reaction solvent. Alternatively, a reaction solvent 
may be additionally used if needed. Any solvent may be employed as a 
reaction solvent so long as it does not affect adversely on the present 
reaction. However, hydrocarbon solvents are suitable. Among such 
hydrocarbon solvents, there are aliphatic hydrocarbons such as pentane, 
hexane, heptane, octane and the like, aromatic hydrocarbons such as 
benzene, toluene, xylene, etc., alicyclic hydrocarbons such as 
cyclopentane, cyclohexane and the like, and mixtures thereof. 
By carrying out the reaction as described above, the 1,3-dioxolan compound 
(II) can be obtained with a high yield of 80% or more. It may be purified 
by distillation or the like if needed. However, it can be furnished for 
the subsequent reaction as is without conducting its isolation and 
purification because it is usually obtained as colorless, odor-free, clear 
liquid. 
The 1,3-dioxolan compound is then etherified into its corresponding dialkyl 
ether oxolan compound (IV). It is preferred to conduct this etherification 
reaction in the presence of an alkaline substance. 
Exemplary alkaline substances may include alkali metal hydroxides, alkali 
metal carbonates, alkali metal phosphates, etc. Among these substances, 
alkali metal hydroxides such as sodium hydroxide and potassium hydroxide 
are particularly suitable from the industrial viewpoint. It is preferable 
to use such an alkaline substance in an amount of 1-10 moles per mole of 
the dioxolan compound (II) as a 10-80%, and more preferably 30-60% aqueous 
solution. 
As etherification agents suitable for use in etherifying the 1,3-dioxolan 
compound (II), alkyl halides, alkyl sulfonates, alkyl sulfates and the 
like may be used. These etherification agents contain a saturated or 
unsaturated, straight chain or branched, aliphatic hydrocarbon group 
having 1-24, and preferably 1-18 carbon atoms. Accordingly, exemplary 
etherification agents include alkyl halides such as alkyl chlorides, alkyl 
bromides and alkyl iodides, alkyl para-toluene sulfonates, alkyl methane 
sulfonates, etc. Among such etherification agents, alkyl bromides and 
alkyl iodides may be mentioned as suitable etherification agents. As alkyl 
groups of such alkyl bromides and alkyl iodides, there may be mentioned, 
as straight chain aliphatic hydrocarbon groups, methyl, ethyl, propyl, 
butyl, octyl, decyl, hexadecyl, octadecyl, octadecenyl(oleyl), and the 
like; as branched aliphatic hydrocarbon groups, 2-ethylhexyl, 
2-heptylundecyl, 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)octyl, a 
methyl-branched isostearyl group represented by the following formula: 
##STR5## 
wherein m stands for integers ranging from 4 to 10, n means integers 
ranging from 5 to 11, m+n ranges 11 to 17, and the methyl branched 
isostearyl group has a distribution with a peak at m=7 and n=8, and the 
like; and as alicyclic hydrocarbon groups, cyclohexyl, cyclopentyl, 
cyclooctyl, etc. In addition, aromatic hydrocarbon groups may also be used 
but aliphatic hydrocarbon groups are particularly suitable in the present 
invention. The etherification agents may be employed in any proportions 
but are suitably used in an amount of 1-6 moles or so per mole of the 
dioxolan compound (II). 
It is preferred to conduct the etherification reaction of the 1,3-dioxolan 
compound (II) in the presence of a catalytic amount of a quaternary onium 
salt. As such a quaternary onium salt usable at this stage, ammonium salts 
are preferred particularly for their availability in an industrial scale. 
As specific example of such quaternary ammonium salts, may be mentioned 
tetraalkylammonium salts (for example, tetrabutylammonium chloride, 
tetrabutylammonium hydrogensulfate, trioctylmethylammonium chloride, 
lauryltrimethylammonium chloride, stearyltrimethylammonium chloride, 
benzyltrimethylammonium chloride, etc.); a class of alkyl ammonium salts 
containing a polyoxyalkylene group (for instance, tetraoxyethylenestearyl 
dimethylammonium chloride, bis-tetraoxyethylenestearyl methylammonium 
chloride, and the like); as well as betaine compounds, crown ethers, amine 
oxide compounds, ion-exchange resins, etc. These quaternary onium salts 
may be used in a catalytic amount. More specifically, it is suitable to 
use them in an amount of 0.005-0.5 mole per mole of the dioxolan compound 
(II). 
Furthermore, regarding the reaction solvent, anything may be employed 
unless it affects adversely on the present reaction. Among those 
particularly preferred, are included aliphatic hydrocarbons such as 
hexane, heptane and octane, alicyclic hydrocarbons such as cyclopentane 
and cyclohexane, and aromatic hydrocarbons such as benzene, toluene and 
xylene. Besides, ether compounds such as diethyl ether, THF, diglyme, 
dioxane and the like may equally be used. 
The hydrolysis reaction of the dialkyl ether (IV) of the 1,3-dioxolan 
compound may be carried out in accordance with any methods known as 
hydrolysis methods for dioxolan. It is however preferred to conduct the 
hydrolysis reaction by using a protonic acid catalyst such as sulfuric 
acid, hydrochloric acid, nitric acid, phosphoric acid, benzene sulfonic 
acid or acetic acid and heating the dialkyl ether (IV) in water. There is 
no special limitation vested to the amount of the acid catalyst to be 
incorporated. A range of 0.01-2N is sufficient but a particularly suitable 
range is 0.05-1N. The hydrolysis reaction may be carried out by adding, to 
water, a water-soluble organic solvent for example a lower alcohol such as 
methanol, ethanol or isopropanol, THF, dioxane, or the like. A preferred 
reaction temperature ranges from 50.degree. C. to 100.degree. C. 
Upon conducting the hydrolysis reaction under such conditions, the intended 
compound, diglycerin dialkyl ether (I) can be obtained substantially in a 
stoichiometric amount from the dialkyl ether dioxolan (IV). 
Although it is most convenient and preferred to prepare the diglycerin 
dialkyl ether (I) of this invention in accordance with the above process, 
it may also be obtained by another process. Namely, following the 
below-described reaction formulae, the diglycerin dialkyl ether may be 
obtained by reacting an alcohol (VII) with an epoxide compound (VIII) of 
the 1,3-dioxolan type in the presence of an acidic or basic catalyst to 
form a 1,3-dioxolan compound (II) and then treating the 1,3-dioxolan 
compound (II) in a manner similar to that mentioned above. 
##STR6## 
wherein R and R' have the same significance as defined above, and X is a 
halogen atom or the like. 
The latter preparation route is however accompanied by a number of 
by-products which occur upon the formation of the 1,3-dioxolan compound 
(II) and the final diglycerin dialkyl ether (I) is thus insufficient in 
purity. Accordingly, the latter preparation route requires a further step 
such as distillation at the end thereof. The inventors tried to determine 
the chemical structure of the diglycerin dialkyl ether (I) obtained in 
accordance with this invention, using the diglycerin dialkyl ether 
resulted from the latter preparation route. It was in fact found that the 
intermediate compound, 1,3-dioxolan compound (II), had an extremely low 
level of yield, namely, about 30% or so when a basic catalyst was employed 
and about 35% or so when an acidic catalyst was relied upon (see, 
Comparative Examples 1-3). 
Among all the 2,3-dialkoxypropyl glyceryl ethers represented by the general 
formula (I) according to this invention, those containing lower alkyl 
groups having 1-3 carbon atoms as R' are especially useful as emulsifiers 
for cosmetic compositions owing to their strong emulsification capacity. 
They show stronger nature as oil as the carbon number of R' becomes 
greater. 2,3-dialkoxypropyl glyceryl ethers containing 4-18 carbon atoms 
are especially useful as oily components for cosmetic compositions. Their 
contents in each cosmetic composition may vary depending on various 
parameters but about 0.2-15 wt% or so is preferred. 
The invention will hereinafter be described in detail with reference to the 
following examples. However, it should be noted that the present invention 
shall not be limited thereto. 
Preparation of alcohols, which serve as starting materials for glycidyl 
ethers, will also be given as Referential Examples.

REFERENTIAL EXAMPLE 1 
Into a 1-liter, round-bottomed flask equipped with a reflux condenser, 
thermometer, dropping funnel and stirrer, were added 120 g of 50% aqueous 
solution of sodium hydroxide (60 g or 1.5 moles as pure sodium hydroxide), 
68 g (0.25 mole) of monomethyl-branched isostearyl alcohol obtained in 
Referential Example 2, 200 ml of n-hexane and 2.51 g (0.0075 mole) of 
stearyl trimethylammonium chloride in the order as they have appeared 
above. The resulting reaction mixture was maintained at a reaction 
temperature of 25.degree. C. in a water bath. While vigorously stirring 
the reaction mixture at a stirring speed of 400 r.p.m., 93 g (1 mole) of 
epichlorohydrin was dropped from the dropping funnel. After completing the 
dropwise addition of epichlorohydrin in the course of about 1.5 hours, the 
temperature of the reaction mixture was raised to 50.degree. C., where it 
was stirred approximately for further 8 hours. Upon completion of the 
reaction, the reaction mixture was treated in the manner routinely 
employed in the art to obtain 68 g of monomethyl-branched isostearyl 
glycidyl ether represented by the following formula (yield: 33%). 
Melting point: 142.degree.-175.degree. C. (0.08 mmHg). 
IR (liquid film, cm.sup.-1): 3050, 3000, 1250, 1100, 920, 845. 
##STR7## 
wherein m stands for integers ranging from 4-10, n means integers ranging 
from 5 to 11, m+n ranges 11 to 17, an the ether has a distribution with a 
peak at m=7, n=8. 
REFERENTIAL EXAMPLE 2 
Charged in a 20-liter autoclave, were 4770 g of isopropyl isostearate 
(Emery 2310 Isopropyl Isostearate, commercially available from Emery 
Industries Inc., U.S.A.) and 239 g of a copper-chromium catalyst (product 
of JGC Corporation). The flask was then filled with hydrogen gas at a 
pressure of 150 kg/cm.sup.2 and the reaction mixture was then heated to 
275.degree. C. After carrying out the hydrogenation for about 7 hours 
under 150 kg/cm.sup.2 /275.degree. C., the reaction product was cooled and 
the catalyst residue was filtered off, thereby obtaining a crude reaction 
product in an amount of 3500 g. Upon distilling the crude reaction product 
under reduced pressures, 3300 g of colorless, clear isostearyl alcohol was 
obtained as a 80.degree.-167.degree. C./0.6 mmHg fraction. The 
thus-obtained isostearyl alcohol (monomethyl-branched isostearyl alcohol) 
had an acid value of 0.05, saponification value of 5.5 and hydroxyl value 
of 181.4. Its IR analysis (liquid film) showed absorption at 3340 and 1055 
cm.sup.-1, while its NMR (CCl.sub.4 solvent) analysis developed absorption 
at .delta. 3.50 (broad triplet, --CH.sub.2 --OH). From its gas 
chromatographic analysis, the main component of the isostearyl alcohol was 
found to be a mixture which consisted of about 75% of an isostearyl 
alcohol containing in total 18 carbon atoms in its alkyl group and the 
remainder of isostearyl alcohols respectively containing 14 and 16 carbon 
atoms as the total carbon numbers of their alkyl groups, each of the 
isostearyl alcohols containing its branched methyl group near the center 
of its main alkyl chain. 
EXAMPLE 1 
(1) Into a 1-liter reaction vessel equipped with a reflux condenser, 
thermometer, dropping funnel and stirrer, were placed 298 g (2.25 moles) 
of acetone glycerin ketal and 12.9 g (0.075 mole) of tetramethyl 
diaminohexane. They were mixed together. The reaction mixture was heated 
to 100.degree. C., followed by a slow, dropwise addition of 140 g (0.75 
mole) of octyl glycidyl ether from the dropping funnel. The temperature of 
the reaction mixture was maintained at 100.degree.-110.degree. C. during 
the dropwise addition of glycidyl ether. It took about 30 minutes until 
the dropwise addition of glycidyl ether was finished. Then, the reaction 
mixture was heated at 100.degree.-110.degree. C. for 6 hours. Subsequent 
to its cooling, excess acetone glycerin ketal, etc. were evaporated under 
reduced pressures from the reaction mixture. Upon subjecting the remainder 
to distillation under reduced pressures, 203 g of colorless, clear liquid 
was obtained (yield: 85%). Its gas chromatographic analysis showed a 
single peak, whereby confirming that the colorless, clear liquid was 
2,2-dimethyl-4-(2'-hydroxy-3'-octoxy)-propoxymethyl-1,3-dioxolan. 
Boiling point: 172.degree.-175.degree. C. (0.6 mmHg). 
Elementary analysis: Calculated for C.sub.17 C.sub.34 O.sub.5 (%): C, 
64.12; H, 10.76; O, 25.12. Found(%): C, 63.9; H, 10.8; O, 24.7. 
IR (liquid film, cm.sup.-1): 3470, 1380, 1370, 1255, 1212, 1110, 1080, 
1050, 840 
NMR (CCl.sub.4 solvent, .delta.): 3.3-4.4 (multiplet, 13H, 
##STR8## 
1.4 (broad singlet, 12H, CH.sub.3 (CH.sub.2).sub.6 CH.sub.2 O--); 0.95 
(triplet, 3H, CH.sub.3 (CH.sub.2).sub.6 CH.sub.2 O--). 
Acid value: 0.01 (found), 0.0 (calculated). 
Saponification value: 0.03 (found), 0.0 (calculated). 
Hydroxyl value: 180 (found), 176 (calculated). 
Iodine value: 0.1 (found), 0.0 (calculated). 
Oxirane oxygen: 0% (found), 0% (calculated). 
Molecular weight (VPO method/CHCl.sub.3): 318 (found), 318 (calculated). 
(2) Added to a 1-liter reaction vessel equipped with a reflux condenser, 
thermometer, dropping funnel and stirrer were first 49.5 g of 97% NaOH (48 
g, i.e., 1.2 moles as NaOH) and then 46.5 g of water to obtain a 50% 
aqueous NaOH solution, followed by further addition of 150 g of hexane and 
63.7 g of 2,2-dimethyl-4-(2'-hydroxy-3'-octoxy)-propoxymethyl-1,3-dioxolan 
(0.2 mole) obtained in Procedure (1) of Example 1. Then, the resultant 
reaction mixture was agitated vigorously, followed by an addition of 3.4 g 
(0.01 mole) of tetrabutyl ammonium hydrogensulfate. The reaction mixture 
was maintained at 25.degree. C., to which reaction mixture was dropped 
little by little 85.2 g (0.6 mole) of methyl iodide from the dropping 
funnel. Upon completion of the dropwise addition, the reaction mixture was 
heated to 50.degree. C., where it was stirred approximately for further 5 
hours. After confirming through a gas chromatographic analysis on the 
reaction mixture that the monoalkyl ether was not present any longer, the 
reaction mixture was cooled and decanted to collect the hexane layer. 
Subsequent to drying the thus-collected hexane layer with sodium sulfate, 
hexane was evaporated under reduced pressures. Thereafter, its 
distillation under reduced pressures gave 56.6 g of 
2,2-dimethyl-4-(2'-methoxy-3'-octoxy)propoxymethyl-1,3-dioxolan as 
colorless, clear liquid (yield: 85%). 
Boiling point: 154.degree.-158.degree. C. (0.7 mmHg). 
Elementary analysis: Calculated for C.sub.18 H.sub.36 O.sub.5 (%): C, 
65.03; H, 10.91, O, 24.06. Found (%): C, 64.9; H, 10.8; O, 24.1. 
IR (liquid film, cm.sup.-1): 1380, 1370, 1260, 1213, 1115, 1055, 850. 
NMR (CCl.sub.4 solvent, TMS internal reference, .delta.): 3.1-4.3 
(multiplet, 12H; 
##STR9## 
3.35 (singlet, 3H; --OCH.sub.3); 1.30 (singlet, 6H; 
##STR10## 
1.25 (broad singlet, 12H, CH.sub.3 (CH.sub.2).sub.6 CH.sub.2 O--); 0.89 
(triplet, 3H, CH.sub.3 (CH.sub.2).sub.6 CH.sub.2 O--). 
Acid value: 0.03 (found), 0.0 (calculated). 
Saponification value: 0.05 (found), 0.0 (calculated). 
Hydroxyl value: 0.10 (found), 0.0 (calculated). 
Iodine value: 0.05 (found), 0.0 (calculated). 
Oxirane oxygen: 0% (found), 0% (calculated). 
Molecular weight (VPO method/CHCl.sub.3): 335 (found), 332 (calculated). 
(3) Two hundred milliliters (200 ml) of a 1N aqueous solution of sulfuric 
acid were charged into a 1-liter reaction vessel equipped with a reflux 
condenser, thermometer and stirrer, followed by further addition of 66.4 g 
(0.2 mole) out of the 
2,2-dimethyl-4-(2'-methoxy-3'-octoxy)propoxymethyl-1,3-dioxolan obtained 
by repeating Procedure (2) of Example 1 twice and then 200 ml of ethanol. 
The reaction mixture was heated and refluxed with stirring. The reaction 
mixture looked like a milky, uneven emulsion in the beginning but, as soon 
as the refluxing started, it turned to a colorless, clear, uniform 
solution. It was heated and refluxed for about 6 hours and the resultant 
reaction mixture was cooled and neutralized by the addition of 8.3 g of 
97% NaOH. After the neutralization, 300 ml of ether was added and the 
ether layer was collected through decantation. It was dried with sodium 
sulfate and its ether was driven off under reduced pressures. Thereafter, 
it was dried for about 3 hours under a reduced pressure of 0.1 mmHg at 
100.degree. C. Thus, 57 g of 2-methoxy-3-octoxypropyl glyceryl ether was 
resulted as colorless, clear, viscous liquid (yield: 98%). 
Elementary analysis: Calculated for C.sub.15 H.sub.32 O.sub.5 (%): C, 
61.61; H, 11.03; O, 27.36. Found (%): C, 61.4; H, 11.0; O, 27.1. 
IR (liquid film, cm.sup.-1): 3400, 1000-1170, 850. 
NMR (CCl.sub.4 solvent, TMS internal reference, .delta.): 4.10 (singlet, 
2H; 
##STR11## 
3.41 (singlet, 3H; --OCH.sub.3); 3.10-3.90 (multiplet, 12H; 
##STR12## 
1.3 (broad singlet, 12H; CH.sub.3 (CH.sub.2).sub.6 CH.sub.2 O--); 0.88 
(triplet, 3H; CH.sub.3 (CH.sub.2).sub.6 CH.sub.2 O--) 
Acid value: 0.01 (found), 0.0 (calculated) 
Saponification value: 0.03 (found), 0.0 (calculated) 
Hydroxyl value: 380 (found), 384 (calculated) 
Iodine value: 0.0 (found), 0.0 (calculated) 
Molecular weight (VPO method/CHCl.sub.3): 290 (found), 292 (calculated). 
EXAMPLE 2 
(1) Procedure (1) of Example 1 was followed exactly except for the 
employment of 182 g (0.75 mole) of dodecyl glycidyl ether in place of 
octyl glycidyl ether. By effecting similar post treatment, 230 g of 
colorless, clear liquid was obtained (yield: 82%). A gas chromatographic 
analysis showed that the colorless, clear liquid consisted of a single 
component, namely, 
2,2-dimethyl-4-(2'-hydroxy-3'-dodecyloxy)propoxymethyl-1,3-dioxolan. 
Boiling point: 196.degree.-200.degree. C. (0.5 mmHg) 
Elementary analysis: Calculated for C.sub.21 H.sub.42 O.sub.5 (%): C, 
67.34; H, 11.30; O, 21.36. Found (%): C, 67.0; H, 11.4; O, 21.1. 
IR (liquid film, cm.sup.-1): 3470, 1380, 1370, 1255, 1213, 1140, 1080, 
1050, 845. 
NMR (CCl.sub.4 solvent, .delta.): 3.2-4.2 (multiplet, 12H; 
##STR13## 
2.8 (singlet, 1H, 
##STR14## 
1.25 (singlet, 6H, 
##STR15## 
1.20 (broad singlet, 20H, CH.sub.3 (CH.sub.2).sub.10 CH.sub.2 O--); 0.87 
(triplet, 3H, CH.sub.3 (CH.sub.2).sub.10 CH.sub.2 O--). 
Acid value: 0.0 (found), 0.0 (calculated). 
Saponification value: 0.05 (found), 0.0 (calculated). 
Hydroxyl value: 155 (found), 150 (calculated). 
Iodine value: 0.3 (found), 0.0 (calculated). 
Oxirane oxygen: 0% (found), 0% (calculated). 
Molecular weight (VPO method/CHCl.sub.3): 376 (found), 375 (calculated). 
(2) Using 74.9 g (0.2 mole) of 
2,2-dimethyl-4-(2'-hydroxy-3'-dodecyloxy)propoxymethyl-1,3-dioxolan 
obtained in Procedure (1) of Example 2, a reaction was carried out under 
the same conditions as those employed in Procedure (2) of Example 1. 
Similar post treatment provided 71.5 g of colorless, clear liquid (yield: 
92%). A gas chromatographic analysis confirmed that it consisted of a 
single component, i.e., 
2,2-dimethyl-4-(2'-methoxy-3'-dodecyloxy)propoxymethyl-1,3-dioxolan. 
Boiling point: 180.degree.-185.degree. C. (0.4 mmHg). 
Elementary analysis: Calculated for C.sub.22 H.sub.44 O.sub.5 (%): C, 
68.00; H, 11.41; O, 20.59; Found (%): C, 67.4; H, 11.4; O, 20.8. 
IR (liquid film, cm.sup.-1): 1380, 1370, 1260, 1216, 1115, 1050, 845. 
NMR (CCl.sub.4 solvent, TMS internal reference, .delta.): 3.2-4.3 
(multiplet, 12H; 
##STR16## 
3.34 (singlet, 3H; --OCH.sub.3); 1.3 (singlet; 6H; 
##STR17## 
1.27 (broad singlet, 20H; CH.sub.3 (CH.sub.2).sub.10 CH.sub.2 O--); 0.85 
(triplet, 3H; CH.sub.3 (CH.sub.2).sub.10 CH.sub.2 O--). 
Acid value: 0.10 (found), 0.0 (calculated). 
Saponification value: 0.30 (found), 0.0 (calculated). 
Hydroxyl value: 0.05 (found), 0.0 (calculated). 
Iodine value: 0.20 (found), 0.0 (calculated). 
Oxirane oxygen: 0% (found), 0% (calculated). 
Molecular weight (VPO method/CHCl.sub.3): 382 (found), 389 (calculated). 
(3) Procedure (3) of Example 1 was exactly repeated except that 77.7 g (0.2 
mole) out of the 
2,2-dimethyl-4-(2'-methoxy-3'-dodecyloxy)propoxymethyl-1,3-dioxolan, which 
had been obtained by repeating Procedure (2) of Example 2 twice, was used 
to carry out its hydrolysis. The reaction mixture looked like a milky 
emulsion in the beginning of the reaction but it turned to a colorless, 
clear, uniform solution as soon as its refluxing started. Through similar 
post treatment, 68.3 g of 2-methoxy-3-dodecyloxypropyl glyceryl ether was 
resulted as colorless, clear, viscous liquid (yield: 98%). 
Elementary analysis: Calculated for C.sub.19 H.sub.40 O.sub.5 (%): C, 
65.48; H, 11.57; O, 22.95. Found (%): C, 65.3; H, 11.2; O, 22.8. 
IR (liquid film, cm.sup.-1): 3400, 1000-1170, 850. 
NMR (CCl.sub.4 solvent, TMS internal reference, .delta.): 3.78 (singlet, 
2H; 
##STR18## 
3.45 (singlet, 3H; --OCH.sub.3); 3.18-3.68 (multiplet, 12H; 
##STR19## 
1.33 (broad singlet, 20H; CH.sub.3 (CH.sub.2).sub.10 CH.sub.2 O--); 0.89 
(triplet, 3H; CH.sub.3 (CH.sub.2).sub.10 CH.sub.2 O--). 
Acid value: 0.03 (found), 0.0 (calculated). 
Saponification value: 0.02 (found), 0.0 (calculated). 
Hydroxyl value: 325 (found), 322 (calculated). 
Iodine value: 0.0 (found), 0.0 (calculated). 
Molecular weight (VPO method/CHCl.sub.3): 350 (found), 349 (calculated). 
EXAMPLE 3 
(1) Into a 5-liter, round-bottomed flask equipped with a reflux condenser, 
thermometer, dropping funnel, nitrogen gas feed line and stirrer, were 
charged 1061 g (8 moles) of glycerin dimethyl ketal and 28.4 g (0.165 
mole) of tetramethyl-1,6-diaminohexane. They were agitated and mixed under 
a nitrogen gas stream. While aerating the flask with nitrogen gas, 1308 g 
(4 moles) of the monomethyl-branched isostearyl glycidyl ether obtained in 
Referential Example 1 was dropped little by little from the dropping 
funnel. Here, the temperature of the reaction mixture was maintained 
around 100.degree. C. by heating same during the dropwise addition of the 
glycidyl ether. The glycidyl ether was added in the course of about 2 
hours, during which the temperature of the reaction mixture rose slowly 
and reached 125.degree. C. when the dropping of the glycidyl ether was 
completed. The reaction mixture was then heated with stirring 
approximately for further 6 hours within a reaction temperature range of 
130.degree.-140.degree. C. After confirming through a gas chromatographic 
analysis on the reaction mixture that all the isostearyl glycidyl ether 
had been used up, 1500 g city water and then 100 g of salt were 
successively added. The resultant mixture was allowed to stand and then 
decanted. The upper layer was collected through the decantation, dried 
with sodium sulfate, and then distrilled under reduced pressures to drive 
off the glycerin dimethyl ketal which was used in an excess amount, 
thereby obtaining 1510 g of 
2,2-dimethyl-4-(2'-hydroxy-3'-isostearoxy)propoxymethyl-1,3-dioxolan 
(yield: 82%). 
Boiling point: 210.degree.-230.degree. C. (0.5-0.8 mmHg). 
Elementary analysis: Calculated for C.sub.27 H.sub.54 O.sub.5 (%): C, 
70.62; H, 11.85; O, 17.42. Found (%): C, 70.7; H, 12.1; O, 16.9. 
IR (liquid film, cm.sup.-1): 3460, 1380, 1370, 1260, 1210, 1115, 1055, 850. 
NMR (CCl.sub.4 solvent, TMS internal reference, .delta.): 3.2-4.3 
(multiplet, 12H; 
##STR20## 
1.3 (singlet, 6H; 
##STR21## 
Acid value: 0.01 (found), 0.0 (calculated). 
Saponification value: 1.5 (found), 0.0 (calculated). 
Hydroxyl value: 120 (found), 122 (calculated). 
Iodine value: 1.0 (found), 0.0 (calculated). 
Oxirane oxygen: 0% (found), 0% (calculated). 
Molecular weight (VPO method/CHCl.sub.3): 458 (found), 459 (calculated). 
(2) Charged in a 3-liter reaction vessel equipped with a reflux condenser, 
thermometer, dropping funnel and stirrer were 240 g of a 50% aqueous 
solution of sodium hydroxide (120 g, i.e., 3.0 moles of sodium hydroxide), 
460 g of hexane, 8.5 g (0.025 mole) of tetrabutyl ammonium 
hydrogensulfate, and 230 g (0.5 mole) of the 
2,2-dimethyl-4-(2'-hydroxy-3'-isostearoxy)propoxymethyl-1,3-dioxolan 
obtained in Procedure (1) of Example 3. They were then vigorously agitated 
at room temperature, followed by a dropwise slow addition of 142 g (1.0 
mole) of methyl iodide from the dropping funnel. The reaction temperature 
was kept at room temperature during the dropping of methyl iodide. After 
completing the addition of methyl iodide, the reaction mixture was heated 
and refluxed. Upon completion of a heating and refluxing operation for 
about 6 hours, the reaction mixture was subjected to a gas chromatographic 
analysis to confirm that the 1,3-dioxolan compound (II) had been entirely 
used up. Thereafter, the reaction mixture was cooled down to room 
temperature, allowed to stand, and decanted. After collecting the organic 
layer, the water layer was extracted with hexane. The hexane layer was 
combined with the organic layer which had been obtained in advance. The 
solvents were evaporated under reduced pressures. A further distillation 
under reduced pressures gave 201 g of 
2,2-dimethyl-4-(2'-methoxy-3'-isostearoxy)propoxymethyl-1,3-dioxolan as 
colorless, clear liquid (yield: 85%). 
Boiling point: 196.degree.-228.degree. C. (0.6-0.8 mmHg). 
Elementary analysis: Calculated for C.sub.28 H.sub.56 O.sub.5 (%): C, 
71.14; H, 11.86; O, 16.92. Found (%): C, 71.0; H, 11.8; O, 17.1. 
IR (liquid film, cm.sup.-1): 1380, 1370, 1260, 1210, 1110, 1050, 850. 
NMR (CCl.sub.4 solvent, TMS internal reference, .delta.): 3.2-4.3 
(multiplet, 12H; 
##STR22## 
3.35 (singlet, 3H; --OCH.sub.3); 1.3 (singlet, 6H; 
##STR23## 
Acid value: 0.12 (found), 0.0 (calculated). 
Saponification value: 0.4 (found), 0.0 (calculated). 
Hydroxyl value: 0.5 (found), 0 (calculated). 
Iodine value: 0.5 (found), 0.0 (calculated). 
Oxirane oxygen: 0% (found), 0% (calculated). 
Molecular weight (VPO method/CHCl.sub.3): 471 (found), 473 (calculated). 
(3) Into a 1-liter reaction vessel equipped with a reflux condenser, 
thermometer and stirrer, were successively added 120 g (0.25 mole) of 
2,2-dimethyl-4-(2'-methoxy-3'-isostearoxy)propoxymethyl-1,3-dioxolan 
obtained in Procedure (2) of Example 3 and then 200 ml of methanol and 200 
ml of a 1N aqueous sulfuric acid solution. They were refluxed under 
heating and stirring. After refluxing them for about 6 hours, it has been 
found from a gas chromatogram obtained on the reaction mixture that the 
hydrolysis of the dialkyl ether dioxolan compound (IV) had proceeded 
completely. The reaction mixture was cooled to room temperature, added 
with 500 ml of ether and then shaken. It was then allowed to stand to 
undergo decantation. The resulting ether layer was collected. Ether was 
evaporated from the ether layer under reduced pressures and the residue 
was dried approximately for 3 hours at 100.degree. C./0.1 mmHg. Thus, 104 
g of 2-methoxy-3-isostearoxypropyl glyceryl ether was obtained in a 
colorless, clear, syrupy state (yield: 96%). 
Elementary analysis: Calculated for C.sub.25 H.sub.52 O.sub.5 (%): C, 
69.40; H, 12.11; O, 18.49. Found (%): C, 69.2; H, 12.0; O, 18.0. 
IR (liquid film, cm.sup.-1): 3400, 1040-1180. 
NMR (CCl.sub.4 solvent, TMS internal reference, .delta.): 3.3-3.8 
(multiplet, 12H; 
##STR24## 
3.5 (singlet, 3H; --OCH.sub.3). 
Acid value: 0.1 (found), 0.0 (calculated). 
Saponification value: 0.5 (found), 0.0 (calculated). 
Hydroxyl value: 250 (found), 260 (calculated). 
Iodine value: 1.0 (found), 0.0 (calculated). 
Oxirane oxygen: 0% (found), 0% (calculated). 
Molecular weight (VPO method/CHCl.sub.3): 435 (found), 433 (calculated). 
EXAMPLE 4 
Procedure (2) of Example 3 was repeated except that 184 g (1 mole) of 
n-butyl iodide was employed in lieu of methyl iodide. The reaction mixture 
was allowed to undergo a reaction at 65.degree.-70.degree. C. for about 20 
hours. Through decantation, an organic layer was collected from the 
reaction mixture. Its solvent was then driven off under reduced pressures. 
Then, the residue was distrilled under reduced pressures, resulting in the 
provision of 210 g of 
2,2-dimethyl-4-(2'-butoxy-3'-isostearoxy)propoxymethyl-1,3-dioxolan as 
colorless, clear liquid (yield: 82%). 
Boiling point: 210.degree.-250.degree. C. (0.7 mmHg). 
Elementary analysis: Calculated for C.sub.31 H.sub.62 O.sub.5 (%): C, 
72.32; H, 12.14; O, 15.54. Found (%): C, 72.1; H, 12.0; O, 15.0. 
IR (liquid film), cm.sup.-1): 1380, 1370, 1260, 1207, 1110, 1060, 845. 
NMR (CCl.sub.4 solvent, TMS internal reference, .delta.): 3.2-4.2 
(multiplet, 14H; 
##STR25## 
1.3 (singlet, 6H; 
##STR26## 
Acid value: 0.10 (found), 0.0 (calculated). 
Saponification value: 0.5 (found), 0.0 (found). 
Hydroxy value: 0.5 (found), 0.0 (calculated). 
Iodine value: 0.3 (found), 0.0 (calculated). 
Oxirane oxygen: 0% (found), 0% (calculated). 
Molecular weight (VPO method/CHCl.sub.3): 517 (found), 515 (calculated). 
(2) Hydrolysis was effected on 134 g (0.26 mole) of 
2,2-dimethyl-4-(2'-butoxy-3'-isostearoxy)propoxymethyl-1,3-dioxolan 
obtained in Procedure (1) of Example 4 in the same manner as in Procedure 
(3) of Example 3. After carrying out similar post treatment, 120 g of 
colorless, clear, syrupy 2-butoxy-3-isostearoxypropyl glyceryl ether was 
obtained (yield: 97%). 
Elementary analysis: Calculated for C.sub.28 H.sub.58 O.sub.5 (%): C, 
70.84; H, 12.31; O, 16.85. Found (%): C, 70.7; H, 12.4; O, 16.8. 
IR (liquid film, cm.sup.-1): 3400, 1040-1180. 
NMR (CCl.sub.4 solvent, TMS internal reference, .delta.): 
3.2-3.8 (multiplet, 14H; 
##STR27## 
Acid value: 0.01 (found), 0.0 (calculated). 
Saponification value: 0.2 (found), 0.0 (calculated). 
Hydroxyl value: 235 (found), 236 (calculated). 
Iodine value: 0.3 (found), 0.0 (calculated). 
Oxirane oxygen: 0% (found), 0% (calculated). 
Molecular weight (VPO method/CHCl.sub.3): 474 (found), 475 (calculated). 
EXAMPLE 5 
(1) Procedure (2) of Example 3 was repeated except that 193 g (1 mole) of 
n-octyl bromide was employed in place of methyl iodide. It was reacted at 
70.degree.-75.degree. C. for about 20 hours. An organic layer was 
collected through decantation from the reaction mixture and its solvent 
was driven off under reduced pressures. The residue was distilled under 
reduced pressures, thereby providing 257 g of 
2,2-dimethyl-4-(2'-octoxy-3'-isostearoxy)propoxymethyl-1,3-dioxolan as 
colorless, clear liquid (yield: 90%). 
Boiling point: 240.degree.-270.degree. C. (0.6-0.7 mmHg). 
Elementary analysis: Calculated for C.sub.35 H.sub.70 O.sub.5 (%): C, 
73.63; H, 12.36; O, 14.01. Found (%): C, 73.9; H, 12.5; O, 14.3. 
IR (liquid film, cm.sup.-1): 1380, 1370, 1260, 1214, 1105, 1055, 845. 
NMR (CCl.sub.4 solvent, TMS internal reference, .delta.): 3.2-4.2 
(multiplet, 14H; 
##STR28## 
1.3 (singlet, 6H; 
##STR29## 
Acid value: 0.1 (found), 0.0 (calculated). 
Saponification value: 0.3 (found), 0.0 (calculated). 
Hydroxyl value: 0.0 (found), 0.0 (calculated). 
Iodine value: 0.1 (found), 0.0 (calculated). 
Oxirane oxygen: 0% (found), 0% (calculated). 
Molecular weight (VPO method/CHCl.sub.3): 573 (found), 571 (calculated). 
(2) Hydrolysis was effected on 171 g (0.3 mole) of 
2,2-dimethyl-4-(2'-octoxy-3'-isostearoxy)propoxymethyl-1,3-dioxolan 
obtained in Procedure (1) of Example 5 in the same manner as in Procedure 
(3) of Example 3. Upon carrying out post treatment in much the same way, 
155 g of colorless, clear, syrupy 2-octoxy-3-isostearoxypropyl glyceryl 
ether was resulted (yield: 97.5%). 
Elementary analysis: Calculated for C.sub.32 H.sub.66 O.sub.5 (%): C, 
72.40; H, 12.53; O, 15.07. Found (%): C, 72.8; H, 12.7; O, 14.6. 
IR (liquid film, cm.sup.-1): 3400, 1020-1170. 
NMR (CCl.sub.4 solvent, TMS internal reference, .delta.): 3.2-3.8 
(multiplet, 14H; 
##STR30## 
Acid value: 0.02 (found), 0.0 (calculated). 
Saponification value: 0.1 (found), 0.0 (calculated). 
Hydroxyl value: 205 (found), 210 (calculated). 
Iodine value: 0.3 (found), 0.0 (calculated). 
Oxirane oxygen: 0% (found), 0% (calculated). 
Molecular weight (VPO method/CHCl.sub.3): 533 (found), 531 (calculated). 
COMATIVE EXAMPLE 1 
In a 3-liter reaction vessel equipped with a reflux condenser, thermometer, 
dropping funnel and stirrer, were placed 720 g of a 50% aqueous solution 
of potassium hydroxide (360 g, i.e., 9 moles, as potassium hydroxide), 400 
g of hexane, and 397 g (3 moles) of acetone glycerin ketal. They were 
vigorously agitated. Thereafter, 39.6 g (0.15 mole) of 
trimethyldodecylammonium chloride was added, followed by maintaining the 
reaction mixture at 30.degree. C. Then, 555 g (6 moles) of epichlorohydrin 
was dropped little by little from the dropping funnel. It took about two 
hours until the entire epichlorohydrin was dropped. The reaction mixture 
was then heated to 50.degree. C. and stirred under heating at the same 
temperature for approximately further 2 hours. The resulting reaction 
mixture was cooled and decanted. The thus-obtained hexane layer was dried 
with sodium sulfate and hexane was then driven off. The residue was 
thereafter subjected to distillation under reduced pressures, resulting in 
440 g of the intended 
2,2-dimethyl-4-(2',3'-epoxy)propoxymethyl-1,3,-dioxolan (yield: 78%). 
Boiling point: 91.degree.-94.degree. C. (2.5 mmHg)--Literature value: 
92.degree.-94.degree. C./2.5 mmHg [J. F. Prak. Chemie, 316, 325-336 
(1974)]. 
COMATIVE EXAMPLE 2 
In a 1-liter reaction vessel equipped with a reflux condenser, thermometer, 
dropping funnel and stirrer, were placed 117 g (0.9 mole) of octyl alcohol 
and 5.2 g (0.03 mole) of tetramethyl diaminohexane. They were heated to 
100.degree. C. and mixed together. Then, 56.5 g (0.3 mole) of 
2,2-dimethyl-4-(2',3'-epoxy)porpoxymethyl-1,3-dioxolan obtained in the 
above Comparative Example 1 was added slowly from the dropping funnel. 
During the dropping period, the reaction mixture was maintained within a 
temperature range of 100.degree.-110.degree. C. They were allowed to react 
each other for about 6 hours within the same temperature range. The 
resulting reaction mixture was cooled, neutralized with dilute 
hydrochloric acid, and decanted to collect an organic layer. Upon carrying 
out distillation under reduced pressures, 29 g of colorless, clear liquid 
was resulted (yield: 31%). Its boiling point, gas chromatogram, IR 
spectrum and NMR spectrum were in conformity with their corresponding data 
obtained on the 1,3-dioxolan compound resulted in Procedure (1) of Example 
1 which relates to the present invention. 
COMATIVE EXAMPLE 3 
The procedure of Comparative Example 2 was repeated except for the 
substitution of 4.2 g (0.03 mole) of boron trifluoride-ether complex for 
tetramethyl diaminohexane which was used as a catalyst. Upon carrying out 
distillation under reduced pressures, 33.4 g of colorless, clear liquid 
was obtained (yield: 35%). Its boiling point, gas chromatogram, IR 
spectrum and NMR spectrum coincided with their corresponding data on the 
1,3-dioxolan compound obtained in Procedure (1) of Example 1 which relates 
to the present invention. 
EXAMPLE 6 
Physical and chemical properties of the compound prepared in Example 1, 
which compound relates to the present invention, and an example of its 
application for cosmetic compositions will be described below. 
______________________________________ 
Viscosity Water-solubility (25.degree. ) 
(27.degree. C.) 
10%* 50%* 
______________________________________ 
423 cp Dissolved Dissolved 
______________________________________ 
* Content (%) of the diglycerin dialkyl ether according to this invention 
These figures will have the same significance in subsequent examples. 
An emulsion having the following composition was formulated: 
______________________________________ 
Liquid paraffin 14.0 (wt. %) 
Squalane 14.0 
A 2-Methoxy-3-octoxypropyl 
2.0 
glyceryl ether (this invention) 
Sodium benzoate 0.2 
B Glycerin 4.0 
Purified water Balance 
______________________________________ 
All the components in Group A were mixed and heated to 75.degree. C. All 
the components in Group B were mixed and heated to 70.degree. C. on the 
side. Thus-mixed and heated components in Group B were then added to the 
mixture of the components in Group A while stirring the latter and 
carrying out emulsification. Then, the resultant mixture was cooled with 
stirring to room temperature, resulting in an emulsion. 
The thus-obtained emulsion was w/o-type emulsified cream. It had extremely 
good stability as an emulsion and developed no separation over a long 
period of time. When applied to skin, it was very compatible with skin and 
was easy and comfortable to apply. Thus, the emulsion was suited as 
cosmetic cream. 
EXAMPLE 7 
Physical and chemical properties of the compound prepared in Example 2, 
which compound relates to the present invention, and an example of its 
application for cosmetic composition will be described below. 
______________________________________ 
Viscosity Water-solubility (25.degree. C.) 
(27.degree. C.) 
10%* 50%* 
______________________________________ 
504 cp Dissolved Liquid Crystal 
formed 
______________________________________ 
An emulsion having the following composition was formulated in a manner 
similar to that employed in Example 6. 
______________________________________ 
Spindle oil 40.0 (wt. %) 
Beef tallo 12.0 
2-Methoxy-3-dodecyloxypropyl 
3.2 
glyceryl ether (this invention) 
Purified water Balance 
______________________________________ 
The resultant emulsion was a w/o-type creamy emulsion. Emulsified particles 
had a very fine mean diameter as little as about 1 micrometer. It showed 
good stability as an emulsion over a prolonged time period and had 
excellent properties as a metal-machining oil. 
EXAMPLE 8 
Physical and chemical properties of the compound prepared in Example 3, 
which compound relates to the present invention, and an example of its 
application for cosmetic compositions will be described below. 
______________________________________ 
Viscosity Water-solubility (25.degree. C.) 
(27.degree. C.) 
10%* 50%* 
______________________________________ 
382 cp Dispersed Liquid crystal 
liquid crys- 
formed 
tal formed 
______________________________________ 
An emulsion having the following composition was formulated. 
______________________________________ 
Liquid paraffin 40 (wt. %) 
Carnauba wax 3 
Ceresine 7 
Bees wax 5 
A Vaseline 7 
Lake pigment 6 
2-Methoxy-3-isostearoxypropyl 
2 
glyceryl ether (this invention) 
Propylene glycol 10 
Purified water 20 
______________________________________ 
The components in Group A were heated and mixed uniformly, to which a 
solution obtained by heating and mixing the components in Group B was 
added. The resultant mixture was emulsified and then immediately poured 
into a mold and cooled there. 
The thus-obtained emulsion was a somewhat soft, solid, w/o-type emulsion 
having milky gloss and, after formed into a stick, had excellent 
properties as lip stick. 
EXAMPLE 9 
Physical and chemical properties of the compound prepared in Example 4, 
which compound relates to the present invention, and an example of its 
application for cosmetic compositions will be described below. 
______________________________________ 
Viscosity Water-solubility (25.degree. C.) 
(27.degree. C.) 
10%* 50%* 
______________________________________ 
240 cp Partially Partially 
dispersed dispersed 
(looked like 
(looked like 
an emulsion) 
an emulsion) 
______________________________________ 
A mixture of the following composition was formulated. 
______________________________________ 
Carnauba wax 3 (wt. %) 
Ceresine wax 6 
Candelilla wax 5 
Bees wax 6 
Castor oil 40 
Oleyloleate 26 
Vaseline 10 
2-Butoxy-3-isostearoxypropyl 
4 
glyceryl ether (this invention) 
______________________________________ 
All the above components were heated to 85.degree. C. so that they were 
melted. After thoroughly mixing them together, the resultant mixture was 
poured into a mold and cooled there. 
The resultant mixture was a translucent, soft solid and, when applied to 
skin, it spreaded smoothly without showing stickiness and showed good 
compatibility with skin. Thus, it had excellent properties as lip cream. 
EXAMPLE 10 
Physical and chemical properties of the compound prepared in Example 5, 
which compound relates to the present invention, and an example of its 
application for cosmetic compositions will be described below. 
______________________________________ 
Viscosity Water-solubility (25.degree. C.) 
(27.degree. ) 
10%* 50%* 
______________________________________ 
280 cp Undissolved 
Undissolved 
______________________________________ 
A mixture of the following composition was formulated in the same manner as 
in Example 9. 
______________________________________ 
Carnauba wax 3 (wt. %) 
Ceresine wax 10 
Microcrystalline wax 5 
Castor oil 36 
Squalane 30 
2-Octoxy-3-isostearoxypropyl 
3 
glyceryl ether (this invention) 
Titanium oxide 8 
Micaceous titanium 2 
Ultramarine 3 
______________________________________ 
The resultant mixture was a soft solid of a bluish white color and, when 
used as eye shadow, it was very compatible with skin and exhibited 
excellent properties.