JP2001011172A - Oligoalkyloxirane derivative, its production, and humectant, cosmetic and detergent composition all comprising the same derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an oligoalkyloxirane derivative excellent in moisture retention, not having a sticky feeling, having an adequate oily feeling, sparingly causing odor change with time and capable of suitably being used as a humectant. SOLUTION: This oligoalkyloxirane derivative is expressed by the formula [wherein AO is OCH2CH(CH3) or OCH2CH(CH3CH3); EO is OCH2CH2; AO and EO can be used both in random addition polymerization and block addition polymerization; (1), (m), (n) and (o) are each an average addition mol number of AO and 1 to 4; (a), (b), (c) and (d) are each an average addition mol number of EO and 0 to 3; 5<=(l)+(m)+(n)+(o)<=12; and 0<=(a)+(b)+(c)+(d)<=4], and has a polydispersity of <=1.04, a cloud point of 40-90 deg.C in 50% aqueous solution and an unsaturation degree of <=0.03. This humectant comprises the above oligoalkyloxirane derivative.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to an oligoalkyloxirane derivative in which alkyloxirane is added to diglycerin, a method for producing the same, and a use thereof. More specifically, the molecular weight distribution is narrow, and the cloud point of an aqueous solution is within a certain range. The present invention relates to an oligoalkyloxirane derivative having a low degree of unsaturation, a method for producing the same, a humectant made of the derivative, which does not have stickiness and does not generate odor over time, and a cosmetic and a cleaning agent containing the humectant.

[0002]

2. Description of the Related Art At present, cosmetics, detergents and toilet soaps containing a humectant are increasing due to problems of dry skin and atopy. Examples of the humectant used for these include 1,3-butanediol and polyethylene glycol dialkyl ether as disclosed in JP-A-10-167948. However, when used in the above, there is a problem that sticky feeling remains.

In order to solve this problem, an alkyl oxirane derivative obtained by adding about 1 to 50 moles of an oxirane such as oxirane or methyl oxirane to a polyhydric alcohol having 3 or more functional groups is generally used. is there. Alkyl oxirane derivatives in which an alkyl oxirane is added to a polyhydric alcohol having three or more functional groups can change the balance between hydrophilicity and lipophilicity by changing the number of moles of the alkyl oxirane, thereby providing an arbitrary feeling of use. Methyl oxirane adducts such as glycerin are used as moisturizing ingredients for cosmetics because they can be changed.

[0004]

However, even an alkyl oxirane derivative of a polyhydric alcohol having three or more functional groups is not completely free of stickiness. Stickiness occurs as in the case. In addition, there is also a problem that a stable blending system cannot be formed because the oiliness varies depending on the lot of the raw material. In addition, there is a problem that an odor is easily generated over time.
In the publication, a quality improving method of adding an antioxidant to a polyhydric alcohol alkylene oxide adduct is disclosed. The use of humectants composed of alkyl oxirane derivatives of polyhydric alcohols is restricted due to these problems despite their usefulness, and at present the improvement is strongly desired.

[0005] The present inventors have analyzed a commercially available alkyl oxirane derivative of a polyhydric alcohol having three or more functional groups in order to search for a causative substance of stickiness, and found that there is a distribution in the number of moles of added alkyl oxirane. In particular, derivatives having an average addition mole number of about 1 to 15 moles have 1 to 30% of unreacted polyhydric alcohol remaining, and bifunctional alkyloxirane derivatives in which alkyloxirane is added to water molecules in the system are also secondary. And a broad molecular weight distribution. Such an unreacted polyhydric alcohol, a bifunctional compound and a compound with a high addition mole number cause stickiness as in the case where the polyhydric alcohol is used alone. On the other hand, if the molecular weight distribution is too wide, the balance between the hydrophilicity and the lipophilicity of the product is lost, so that the appropriate oily feeling required for the humectant is impaired.

Further, the cause of the odor of the polyfunctional alkyloxirane derivative was analyzed. As a result, in the commercial product of the alkyloxirane derivative, especially the methyloxirane derivative, the terminal by-produced during the addition reaction was a propenyl group or an allyl group. It contains unsaturated compounds (Yoshikazu Goto,
Journal of Polymers, vol50, No. 2, pp. 121-
126, 1993), it has been found that these compounds are decomposed with time to form propionaldehyde, which is the main cause of odor.

Conventionally, impurities have been examined in high molecular weight alkyloxirane derivatives having a molecular weight of 1,000 or more (Yoshikazu Goto, Journal of the Chemical Society of Japan, 199).
3, (9), 1085-1090), and low addition moles of alkyloxirane derivatives useful as humectants have not been investigated for impurities contained therein, and therefore have a sticky feeling or odor. Nothing was considered in terms of impurities and oiliness.

An object of the present invention is to provide an oligoalkyl oxirane derivative which is excellent in moisturizing properties, has no stickiness, has an appropriate oily feeling, and has little change in odor over time. It is an object of the present invention to provide a production method, a humectant made of this derivative, which does not have stickiness and does not generate odor over time, and a cosmetic and a cleaning agent containing the humectant.

[0009]

The present inventors have conducted intensive studies to obtain a humectant that can be suitably used. As a result, the present invention relates to an alkyloxirane derivative obtained by adding a specific mole number of alkyloxirane starting from diglycerin and having a molecular weight of Alkyl oxirane derivatives having a uniform distribution, a cloud point of a 50% aqueous solution within a certain range, and a low degree of unsaturation are excellent in moisturizing properties, have no stickiness, have an appropriate oily feeling, and have an odor over time. The present inventors have found that there is little change and that they can be suitably used as a humectant, and have reached the present invention.

That is, the present invention provides the following alkyloxirane derivative, a method for producing the same, a humectant comprising this derivative,
And cosmetics and cleaning agents containing the humectant. (1) The polydispersity represented by the formula (1) is 1.040 or less, and the 50% by weight aqueous solution has a cloud point of 40 to 90.
An oligoalkyloxirane derivative having a degree of unsaturation of 0.03 ° C. or less.

[0011]

Embedded image

(However, AO is -OCH_TwoCH (CH_Three)
-Group or -OCH_TwoCH (CH_TwoCH _Three)-Group;
EO is -OCH_TwoCH_TwoAO and EO are land
May be added in the form of a block or block
No. l, m, n and o are oxypropylene groups or
The average number of moles of the added xbutylene group, a, b, c and
d is the average number of moles of oxyethylene groups added, and 1 ≦
l, m, n, o ≦ 4, 0 ≦ a, b, c, d ≦ 3, 5 ≦ l
+ M + n + o ≦ 12, 0 ≦ a + b + c + d ≦ 4
Number. (2) Formula (2) is shown for 1 mol of diglycerin.
0.005 to 0.1 mol of alcoholate catalyst to be used
And remove alcohol under reduced pressure.
Apply kill oxirane or oxirane at 80-110 ° C
The oligo according to the above (1), wherein
A method for producing an alkyloxirane derivative. ROX (2) (where R is a linear or branched hydrocarbon having 1 to 4 carbon atoms)
(3) X is potassium or sodium) (3) Formula (2) is represented by 1 mol of diglycerin.
0.005 to 0.1 mol of alcoholate catalyst to be used
And remove alcohol under reduced pressure.
Apply kill oxirane or oxirane at 80-110 ° C
Reaction, and then the pH of the reaction solution is adjusted to pH in the presence of an antioxidant.
After adjusting to 3 or less, alkaline earth metal oxide or
Treating with an acid sorbent containing a alkaline earth metal hydroxide
The oligoalkyl oxo according to the above (1), characterized in that:
A method for producing a silane derivative. ROX (2) (where R is a linear or branched hydrocarbon having 1 to 4 carbon atoms)
And X is potassium or sodium.) (4) The oligoalkyloxirane derivative according to (1) above
Moisturizer made of conductor. (5) The oligoalkyl oxirane derivative according to the above (1)
A cosmetic comprising 2 to 40% of a conductor. (6) The oligoalkyl oxirane derivative according to the above (1)
A cleaning agent comprising 2 to 40% of a conductor.

[0013]

DETAILED DESCRIPTION OF THE INVENTION In the above formula (1), l, m,
n and o are respectively 1-4, preferably 1-3. The reason that l, m, n and o are each limited to 1 to 4 is that at least 1 mole of each hydroxyl group of glycerin has a sticky feeling when used unless alkyl oxirane is added, and 4 If the amount exceeds the mole, the oily feeling becomes too strong, which is not preferable. Further, l + m + n + o, which is the total number of moles of alkyloxirane added, is 5 to 5.
12, preferably 5 to 10. l + m + n + o is 5
If the total number of added moles is less than 5 moles, the water solubility is so strong that it is difficult to obtain a moist feeling, and if it exceeds 12 moles, on the contrary, the lipophilicity becomes too strong to give a feeling of use. This is because it is not preferable because it is close to oil and a sufficiently moist feeling cannot be obtained.

In the above formula (1), a, b, c and d are each 0 to 3, preferably 0 to 2. a,
When b, c and d are 0, the oxyethylene chain is not introduced, but the oxyethylene chain can be introduced as needed to adjust the balance between hydrophilicity and lipophilicity.
A + b + c which is the total number of added moles of the oxyethylene chain
When + d is more than 4, hydrophilicity becomes too strong, which is not preferable.

The oligoalkyloxirane derivative of the present invention represented by the above formula (1) has a polydispersity of 1.04 or less, preferably 1.03 or less. The polydispersity is an index indicating the molecular weight distribution, and the closer to 1, the narrower the molecular weight distribution and the more uniform the compound. If the unreacted raw material diglycerin remains in the oligoalkyloxirane derivative or the molecular weight distribution is wide due to a non-uniform addition reaction, the polydispersity increases. In fact, if the polydispersity exceeds 1.04, stickiness at the time of use occurs, which is not preferable.

The polydispersity is generally obtained as an elution parameter of gel permeation chromatography (hereinafter, referred to as GPC), and varies greatly depending on a measuring device, a column, a developing solvent and the like. The polydispersity described in the present specification is obtained by dividing the weight average molecular weight (Mw) and the number average molecular weight (Mn), and is expressed as Mw / Mn. Specifically, as a GPC system, SHOdex GPC SYSTEM-11
(Trademark, manufactured by Showa Denko KK), SHO as differential refractometer
DEX RI-71 (trademark, manufactured by Showa Denko KK), GP
SHODEX KF804L (φ8mm
× 300 mm, trade name, manufactured by Showa Denko KK), connected in series, a column constant temperature bath temperature of 40 ° C., tetrahydrofuran (THF) as a developing solvent at a flow rate of 1 ml / min, and 0.1% THF of the sample. 0.1 ml of the solution is injected, and the elution curve is analyzed by a BORWIN GPC calculation program to obtain a polydispersity.

The oligoalkyloxirane derivative of the present invention represented by the above formula (1) has a cloud point of 40 to 90 ° C., preferably 60 to 80 ° C., measured using a 50% by weight aqueous solution of the derivative. The cloud point is determined as a temperature at which a 50% by weight aqueous solution of an oligoalkyloxirane derivative is heated once to make it turbid, and the 50% by weight aqueous solution in which the turbidity is observed is gradually cooled so that the turbidity disappears. The temperature at which the turbidity of the aqueous solution disappears is visually confirmed that the aqueous solution has become transparent.

In general, in an oligoalkyl oxirane derivative, as the number of moles of alkyl oxirane added increases, the hydroxyl group concentration decreases, so that the lipophilicity increases. However, even if the humectant is too hydrophilic, the lipophilicity increases. It is not preferable to be too strong. Since the balance between hydrophilicity and lipophilicity is a sensory problem, it is liable to change depending on the amount of impurities contained in the compound and the like, and it is difficult to quantify the results. It has been found that a 50% by weight aqueous solution of the derivative having a cloud point in the range of 40 to 90 ° C. has a good balance between hydrophilicity and lipophilicity as a humectant. That is, the cloud point is 40
If the temperature is lower than 0 ° C, the oil has too much lipophilicity and feels only as an oil with stickiness. If the cloud point is higher than 90 ° C, the hydrophilicity becomes too strong and it becomes difficult to obtain a moist feeling. If the cloud point is within this range, the film can be used sufficiently as a humectant, but in order to obtain a sufficient moist feeling, it is preferable that the cloud point be in the range of 60 to 80 ° C.

In the oligoalkyloxirane derivative represented by the formula (1), when the number of moles of alkyloxirane is small, the proportion of hydroxyl groups in the molecular structure increases, the cloud point increases, and the number of moles of alkyloxirane increases. As the proportion of hydroxyl groups in the molecular structure decreases, the cloud point decreases. Further, since the oxyethylene chain is a hydrophilic group, the cloud point increases as the number of moles of oxirane added increases. Therefore, the cloud point can be adjusted by selecting the type of alkyloxirane, the number of moles added, and the like.

The oligoalkyloxirane derivative of the present invention represented by the above formula (1) has an unsaturation of 0.03 or less,
Preferably it is 0.02 or less. The degree of unsaturation is an index indicating the content of a group having an unsaturated bond such as an allyl group or a propenyl group contained in an alkyloxirane derivative, and is determined according to JIS K 15576.7.

The fact that the degree of unsaturation is large indicates that the oligoalkyloxirane derivative contains many compounds having an unsaturated bond such as an allyl group and a propenyl group as impurities. Impurities having an allyl group or a propenyl group are decomposed with time to form allyl alcohol or propionaldehyde, and such impurities are the main cause of the deterioration of odor with time. Therefore, the smaller the degree of unsaturation, the better the odor change over time,
If the degree of unsaturation exceeds 0.03, the change in odor with time increases, which is not preferable for cosmetics and cleaning agents.

The oligoalkyl oxirane derivative of the present invention is excellent in moisture retention and has a uniform molecular weight distribution, so that it has no sticky feeling, has an appropriate oily feeling, and has little change in odor with time. For this reason, the oligoalkyl oxirane derivative of the present invention can be used as a very good humectant.

The humectant of the present invention comprises the oligoalkyl oxirane derivative of the present invention. Even if the humectant is composed of only the oligoalkyl oxirane derivative, a known component usually contained in a humectant is replaced by another component. It may be included as. The humectant of the present invention can be specifically used as a humectant in cosmetics and cleaning agents.

The cosmetic of the present invention is a cosmetic containing 2 to 40% by weight, preferably 5 to 20% by weight of the oligoalkyloxirane derivative of the present invention (namely, the humectant of the present invention). Since the cosmetic of the present invention contains the above-mentioned oligoalkyloxirane derivative of the present invention in the above-described amount, a good moist feeling can be obtained. If the blending amount of the oligoalkyloxirane derivative is less than 2% by weight, the moisturizing property cannot be sufficiently exhibited and the moist feeling is insufficient, which is not preferable. If the blending amount exceeds 40% by weight, there is no particular problem in the moisturizing feeling and the moisturizing performance. However, since the amount of other cosmetic ingredients is reduced, the function as a cosmetic cannot be sufficiently exhibited, which is not practical. The preferred range of compounding amount is 5
-20% by weight.

Specific examples of the cosmetic of the present invention include:
Lotion, milky lotion, cleansing cream, hair treatment lotion, hair styling foam, hair styling gel, sunscreen lotion, sunscreen cream, foundation, lipstick, cold cream,
Hand cream, pack, skin cleanser, softening cosmetic,
Nutritional cosmetics, whitening cosmetics, wrinkle improving cosmetics, anti-aging cosmetics, cleansing cosmetics, rinses, treatments, hair styling agents, hair tonics, mascaras, eye shadows, etc.

The components other than the oligoalkyloxirane derivative contained in the cosmetic of the present invention are not particularly limited, and other known cosmetic components which are usually added to cosmetics can be added. Specific examples of other cosmetic ingredients include alcohols such as ethyl alcohol, isopropyl alcohol, tetradecyl alcohol, octadecyl alcohol, hexadecyl alcohol, octadecenyl alcohol, hexyldecyl alcohol, glycerin, and sorbitol;
Hydrocarbons such as liquid paraffin, petrolatum, squalane;
Beeswax, olives, ground wax, carnauba wax,
Vegetable oils such as lanolin, whale wax, animal oils or waxes; stearic acid, palmitic acid, oleic acid, glycerin monostearate, glycerin distearate, glycerin monooleate, isopropyl myristate, isopropyl stearic acid Fatty acids such as esters and butyl stearate or esters thereof; polyoxyethylene hydrogenated castor oil, polyoxyethylene sorbitan monooleate, polyethers such as polyethylene glycol, polypropylene glycol, polyalkylene glycol; polyether-modified silicone, glyceryl ether-modified silicone ,
Emulsifiers for silicone oils such as polyetheralkyl-modified silicones; thickeners such as methylcellulose, ethylcellulose, carboxymethylcellulose, polyacrylic acid, agar, gelatin; surfactants, medicinal ingredients, emulsion stabilizers, chelating agents, pH adjusters , Pigments, colorants, dyes, fragrances, preservatives, water and the like.

The detergent of the present invention is a detergent containing the oligoalkyloxirane derivative of the present invention (that is, the humectant of the present invention) in an amount of 2 to 40% by weight, preferably 5 to 20% by weight. Since the detergent of the present invention contains the oligoalkyloxirane derivative of the present invention in the above-described amount, a good moist feeling can be obtained. If the blending amount of the oligoalkyloxirane derivative is less than 2% by weight, the moisturizing property cannot be sufficiently exhibited and the moist feeling is insufficient, which is not preferable. If the blending amount exceeds 40% by weight, there is no particular problem in the moisturizing feeling and the moisturizing performance. However, since the amount of other detergent components is reduced, the function as a detergent cannot be sufficiently exhibited, which is not practical. The preferred range of compounding amount is 5
-20% by weight. Specific examples of the detergent of the present invention include body soap, shampoo, cleansing lotion and the like.

The components other than the oligoalkyl oxirane derivative contained in the detergent of the present invention are not particularly limited, and other known cosmetic components which are usually incorporated in detergents can be added. Specific examples of other detergent components include alcohols such as ethyl alcohol, isopropyl alcohol, tetradecyl alcohol, octadecyl alcohol, hexadecyl alcohol, octadecenyl alcohol, hexyldecyl alcohol, glycerin, and sorbitol;
Hydrocarbons such as liquid paraffin, petrolatum, squalane;
Beeswax, olives, ground wax, carnauba wax,
Vegetable oils such as lanolin, whale wax, animal oils or waxes; stearic acid, palmitic acid, oleic acid, glycerin monostearate, glycerin distearate, glycerin monooleate, isopropyl myristate, isopropyl stearic acid Fatty acids such as esters and butyl stearate or esters thereof; polyoxyethylene hydrogenated castor oil, polyoxyethylene sorbitan monooleate, polyethers such as polyethylene glycol, polypropylene glycol, polyalkylene glycol; polyether-modified silicone, glyceryl ether-modified silicone ,
Emulsifiers for silicone oils such as polyetheralkyl-modified silicones; thickeners such as methylcellulose, ethylcellulose, carboxymethylcellulose, polyacrylic acid, agar, gelatin; surfactants, medicinal ingredients, emulsion stabilizers, chelating agents, pH adjusters , Pigments, colorants, dyes, fragrances, preservatives, water and the like.

The oligoalkyloxirane derivative of the present invention can be easily obtained, for example, by the following production method. 1) The alcoholate catalyst represented by the above formula (2) is used in an amount of 0.005 to 0.5 to 1 mol of diglycerin in the reaction system.
1 mol, preferably 0.008 to 0.07 mol, is subjected to a dealcoholization treatment under reduced pressure, followed by an addition reaction of alkyloxirane or oxirane at 80 to 110 ° C. 2) The alcoholate catalyst represented by the above formula (2) is used in an amount of 0.005 to 0.5 with respect to 1 mol of diglycerin in the reaction system.
1 mol, preferably 0.008 to 0.07 mol, and after a dealcoholization treatment under reduced pressure, alkyl oxirane or oxirane is subjected to an addition reaction at 80 to 110 ° C. A method in which a reaction solution is adjusted to pH 3 or less, preferably pH 2 to 3 in the presence or absence, and then treated with an acid adsorbent containing an alkaline earth metal oxide or an alkaline earth metal hydroxide.

Specific examples of the alcoholate catalyst represented by the above formula (2) include sodium methoxide, sodium tert-butoxide, potassium methoxide,
Alcohols of alkali metals such as potassium tert-butoxide are mentioned. These alcoholate catalysts can also be used as a C1-C4 alcohol diluent solution for better handling.

In the production method of the present invention, if the amount of the alcoholate catalyst used is less than the lower limit, sufficient catalytic activity cannot be obtained, the reaction becomes difficult and the reaction takes a long time. When it exceeds, the hydroxyl group of diglycerin is not sufficiently converted into an alcoholate at the time of dealcoholation, and oxirane or alkyloxirane is easily added to the alcoholate catalyst, so that by-products are likely to be generated.

The method of adding diglycerin and an alcoholate catalyst is not particularly limited, and a method of mixing diglycerin and an alcoholate catalyst in a reactor can be employed. In the production method of the present invention, after adding diglycerin and an alcoholate catalyst, a dealcoholization treatment is performed under reduced pressure. By performing the dealcoholation treatment, the alcohol generated from the alcoholate catalyst (that is, ROH, where R is R in the formula (2)) is removed. Since alcohol other than diglycerin causes impurities, it is preferable to remove the alcohol as completely as possible so as not to remain in the reaction system.

The dealcoholization treatment is carried out under a flow of an inert gas such as nitrogen at 50 to 100 ° C., preferably 70 to 100 ° C.
At a temperature of 100 mmHg or less, preferably 50 mmHg
g under a reduced pressure of 0.1 g or less, preferably 0.5 to 5 hours.
It is desirable to carry out for up to 2 hours. In the production method of the present invention, since the amount of the alcoholate catalyst used is small, the hydroxyl group of diglycerin can be completely converted into an alcoholate under relatively mild conditions as described above.

After the dealcoholation treatment, the reaction system
Add kill oxirane or oxirane and add alcohol
React with diglycerin. Alkyloxy
Specific examples of orchids include methyloxirane, ethyl
And loxirane. Reaction temperature is 80-11
0 ° C., preferably 90 to 110 ° C. Also reaction time
Is 1 to 20 hours, preferably 2 to 15 hours, and the pressure is 0.1 hour.
3 to 10 kgf / cm ^Two(Gauge pressure)
No. When the reaction temperature exceeds 110 ° C., a propenyl group or
Many unsaturated compounds having an allyl group are by-produced.
If the temperature is lower than ℃, the addition reaction itself is unlikely to occur, so that the
Not good.

According to the above-mentioned method, the oligoalkyloxirane derivative of the present invention having a low impurity content and high purity can be easily produced without almost producing by-products derived from the alcoholate catalyst. The impurities described above can be almost completely removed by performing the purification described in the above method 2), and an oligoalkyloxirane derivative with less odor generation over time can be produced.

The production method 2) is characterized in that a purification step is provided as a post-treatment, and the unsaturated compound which is slightly by-produced during the reaction is once treated with an acid to cleave the unsaturated group. That is, after the reaction, in the presence or absence of an antioxidant, after adjusting the reaction solution to pH 3 or less,
Treatment with an acid adsorbent containing an alkaline earth metal oxide or an alkaline earth metal hydroxide.

In the production method 1), when an allyl group is by-produced during the reaction, the allyl group is relatively quickly transferred to a propenyl group, but the propenyl group remains as an impurity. Therefore, in the production method 2), the propenyl group is cleaved by adjusting the pH of the reaction solution to 3 or less. The propenyl group is rapidly cleaved under the condition that the pH is 3 or less, and is separated into a compound having a hydroxyl group and propionaldehyde. The separated aldehyde groups are removed by an adsorbent and a treatment under reduced pressure. Thereby, impurities are almost completely removed, and a high-purity oligoalkyloxirane derivative can be obtained.

The acid used at this time is p in the reaction solution.
If H can be reduced to 3 or less, various types can be used. Specific examples include hydrochloric acid or phosphoric acid, or a water-diluted product thereof.

It is important to add an antioxidant to the system before treating under acidic conditions. Antioxidants that can be used may be water-soluble or oil-soluble as long as they are compounds having an antioxidant effect, and are not particularly limited. Specific examples of antioxidants include BHT (2, 6
-Di-tert-butyl-p-cresol), butylhydroxyanisole, parahydroxyanisole, α-
Tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol, tocopherol acetate, natural vitamin E, ascorbic acid, sodium ascorbate, ascorbyl palmitate, ascorbyl dipalmitate, erythorbic acid, sodium erysorbate,
Ortolyl biguanide, dilauryl thiodipropionate, tea extract, rosemary extract and the like. Of these, BHT is preferred. One or more antioxidants can be used.

The amount of the antioxidant to be added is not particularly limited as long as it can prevent the oxidative deterioration of the polyalkylene glycol chain during the acid treatment, and is not particularly limited. 30 by weight
It is desirable that the content be set to 500 ppm, preferably 50 to 200 ppm. Although it may be added exceeding the above upper limit,
If it is too large, it is not practical because it is disadvantageous in terms of cost.

The acid adsorbent used in the method of use of the present invention comprises:
Alkaline earth metal oxides, alkaline earth metal hydroxides,
A mixture thereof, or a mixture thereof. Specific examples of the acid adsorbent include magnesium oxide, calcium oxide, barium oxide, magnesium hydroxide, calcium hydroxide, barium hydroxide, and mixtures thereof. Commercial products containing these compounds can also be used. For example, Kyoward 100, Kyoward 300, Kyoward 500, Kyoward 600, Kyoward 1000, Kyoward 2000 (trademark, manufactured by Kyowa Chemical Industry Co., Ltd.) , Tomix AD100, Tomix AD300, Tomix AD500, Tomix A
D600, Tomix AD800 (manufactured by Tomita Pharmaceutical Co., Ltd.)
Trademark) and the like.

The addition time of these adsorbents depends on the reaction system p
It may be any time after adjusting H to 3 or less and before the filtration step. Specifically, a method of adding an acid adsorbent immediately after the completion of the pH adjustment treatment step, dehydrating and then filtering to obtain an intended product; after the pH adjustment treatment step, once performing a dehydration treatment, and then adding the acid adsorbent. And then subjecting the mixture to a reduced pressure treatment, followed by filtration to obtain the desired product.

The amount of the adsorbent to be added is not particularly limited as long as it can adsorb aldehydes and excess acid by-produced by cleavage, but is not particularly limited. Since the pH cannot be returned to the neutral range, the content in the reaction solution is 0.1 to
3% by weight is an appropriate amount. A preferred range is 0.5 to
2% by weight.

By performing the treatment with the acid adsorbent as described above, the pH of the reaction solution returns to 6 to 8. By performing the purification treatment as described above, impurities can be almost completely removed, and a higher-purity oligoalkyloxirane derivative can be obtained.

The oligoalkyloxirane derivative of the present invention is produced by addition-polymerizing oxirane or alkyloxirane to diglycerin in the presence of an alkali catalyst such as an alkali metal hydroxide such as potassium hydroxide or sodium hydroxide. However, when a compound having a hydroxyl group as described above is used as an alkali catalyst, an alkyloxirane is also added to a hydroxyl group in the catalyst.
A large amount of bifunctional alkyloxirane derivative is by-produced.
Since these by-products cause stickiness, when they are used as humectants, they are preferably used after purification to remove by-products. Therefore, the method 1) or 2) is preferable as the manufacturing method.

In order to prevent the formation of a bifunctional alkyloxirane derivative as a by-product, a method of mixing a catalyst and diglycerin and then subjecting the system to a reduced pressure treatment under heating conditions to remove water may be considered. When the alkali catalyst is a compound having a hydroxyl group, the hydroxyl group of glycerin cannot be sufficiently converted to an alcoholate under the temperature range and reduced pressure conditions that can be generally used industrially, so that alkyl oxirane is added to the remaining hydroxyl group derived from the catalyst. The bifunctional derivative is by-produced. Since these by-products cause stickiness, when they are used as humectants, they are preferably used after purification to remove by-products. Therefore, the method 1) or 2) is preferable as the manufacturing method.

As a purification method, known methods such as chromatography can be employed. For example, unreacted diglycerin or water molecules can be purified from an oligoalkyloxirane derivative synthesized using an alkali catalyst by preparative means such as preparative liquid chromatography. 2 with alkyloxirane bonded to
A functional alkyloxirane derivative or a derivative having a terminal unsaturated group by-produced during the reaction can be removed.

[0048]

The oligoalkyl oxirane derivative of the present invention has excellent moisturizing properties, and has a uniform molecular weight distribution, so that there is no stickiness, the oily feeling is moderate, and the odor change with time is small. Can be suitably used.

In the method for producing an oligoalkyl oxirane derivative of the present invention, a specific alcoholate catalyst is brought into contact with diglycerin in a specific amount, dealcoholization treatment is performed under reduced pressure, and then reaction is performed with alkyl oxirane or oxirane. Therefore, a high-purity oligoalkyloxirane derivative having few impurities can be easily and efficiently produced at low cost. Since the oligoalkyl oxirane derivative produced by the production method of the present invention hardly contains impurities containing unsaturated groups, the change in odor with time is small. In addition, as a post-treatment, the reaction solution is adjusted to pH 3 or less in the presence of an antioxidant, and then treated with an acid adsorbent to produce an oligoalkyloxirane derivative with less impurities easily, efficiently, and at low cost. can do.

Since the humectant of the present invention is composed of the above-mentioned oligoalkyloxirane derivative, it has excellent moisturizing properties, no stickiness, moderate oiliness, and little change in odor with time. It can be suitably blended with a detergent. Since the cosmetic of the present invention contains a specific amount of the above-mentioned oligoalkyloxirane derivative, it has excellent moisturizing properties, has no sticky feeling, has an appropriate oily feeling, and has little change in odor with time.

[0051]

The present invention will be described in detail below with reference to examples and comparative examples. In each example, physical properties were measured by the following methods. << Polydispersity >> SHODEX GP as GPC system
C SYSTEM-11 (trademark, manufactured by Showa Denko KK),
SHODEX RI-71 (trademark, manufactured by Showa Denko KK) as a differential refractometer and SHOdex as a GPC column
KF804L (φ8mm × 300mm, Showa Denko KK)
And trademark) are connected in series and the column temperature is 40
° C, tetrahydrofuran (THF) as a developing solvent
The sample was injected at a flow rate of ml / min, 0.1 ml of the sample was injected, and the elution curve was analyzed by a BORWINPC calculation program manufactured by JASCO Corporation to obtain a polydispersity.

<< Cloud Point >> A 50% by weight aqueous solution of an oligoalkyloxirane derivative is placed in a test tube together with a thermometer. The aqueous solution is heated with a thermometer to a temperature higher than the temperature at which turbidity occurs by 2 to 3 ° C. while being well stirred, and then cooled to measure the temperature at which the aqueous solution becomes transparent. << Unsaturation >> Determined according to JIS K 1557 6.7.

Example 1 830 g of diglycerin was placed in a 5-liter autoclave equipped with a nitrogen blowing tube, an injection tube, a stirrer, and a thermometer.
(5 mol) and potassium tertiary butyrate 2
2.4 g (0.2 mol → 4 mol% based on glycerin)
At 90 ± 5 ° C while blowing nitrogen gas.
Dealcoholization treatment was performed for 1 hour while stirring under a vacuum condition of 0 mmHg or less. Then, the reaction system was pressurized to 1.0 kg / cm ² with nitrogen gas,
43.4 g (47.3 mol) at a pressure of 3.5 kg / cm
100 ± 5 ℃ while controlling to ² or less
And gradually press-fitted. After injecting the whole amount, stirring was continued at the same temperature for another 3 hours. Then, the temperature was lowered to 80 ± 5 ° C., and the mixture was treated under a reduced pressure of 100 mmHg or less for 1 hour while blowing nitrogen gas to remove remaining unreacted methyloxirane. Then, the inside of the system was returned to normal pressure with nitrogen gas, and the whole amount was transferred to a 5-liter four-necked flask. The obtained reaction solution was 352
It was 5 g.

The above four-necked flask was equipped with a stirrer, a nitrogen blowing tube, a thermometer, and a vacuum joint.
The pH was adjusted to 2.5 using phosphoric acid. While blowing in nitrogen gas, the mixture was stirred for 1 hour while maintaining the temperature at 60 ± 2 ° C. Next, Kyoward 1000, an acid adsorbent
(Kyowa Chemical Industry Co., Ltd., trademark) 55.1 g (2% by weight based on the reaction solution) was added, and the temperature was increased to 100 ± 5 ° C.
Start vacuuming while blowing nitrogen gas.
After the pressure became 0 mmHg or less, dehydration was continued for another 2 hours. The salt and adsorbent produced as by-products were removed by filtration under reduced pressure to obtain 3,441 g of an oligoalkyloxirane derivative (pH 6.5). FIG. 1 shows a chart of gel permeation chromatography (GPC) of the obtained oligoalkyloxirane derivative.

The polydispersity of the obtained compound was 1.022, the hydroxyl value was 319.2, and the degree of unsaturation was 0.02.
It was one. The cloud point of the 50% aqueous solution was 72.9 ° C. The molecular weight determined from the hydroxyl value was 703.0. From this, when the number of moles of methyloxylan is determined,
Methyloxirane was added in a total of 9.3 mol.

Therefore, the structure of the obtained oligoalkyloxirane derivative can be estimated to be the following formula (3).

[0057]

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Example 2 498 g of diglycerin was placed in a 5-liter autoclave equipped with a nitrogen blowing tube, an injection tube, a stirrer, and a thermometer.
(3 moles) and 1.6 g of sodium methylate (0.
03 mol → 1 mol% based on glycerin), and a dealcoholization treatment was performed for 1 hour with stirring at 80 ± 5 ° C. under a vacuum condition of 50 mmHg or less while blowing nitrogen gas. Next, the inside of the reaction system was 1.0 kg with nitrogen gas.
/ Cm ² (gauge pressure)
901 g (26.4 moles) with a pressure of 3.5 kg / cm ²
The pressure was gradually injected at 100 ± 5 ° C. while controlling as follows. After the entire amount was injected, stirring was continued at the same temperature for another 8 hours. Then, the temperature was lowered to 80 ± 5 ° C., and the pressure was reduced to 100 mmHg or less while blowing nitrogen gas.
The mixture was treated for an hour to remove the remaining unreacted ethyloxirane.

The internal pressure of the system is set to 1.0 kg / cm ² with nitrogen gas.
(Gauge pressure), a 20 g sample of the reaction solution was withdrawn from the sample withdrawal tube into an eggplant-shaped flask, and 2 g of Kyoward 700 (manufactured by Kyowa Chemical Industry Co., Ltd.) as an alkali adsorbent was added. For 30 minutes, and Kyoward was removed by filtration under reduced pressure to obtain 17.4 g of a hydroxyl value measurement sample. The hydroxyl value of the obtained sample was 300.5, and the molecular weight determined from the hydroxyl value was 746.8. From this, the addition mole of ethyl oxirane actually added was calculated to be 8.07 mole.

Subsequently, 290 g (6.6 mol) of oxirane was gradually injected at 100 ± 5 ° C. while controlling the pressure to 4 kg / cm ² (gauge pressure) or less. After injecting the whole amount, stirring was continued at the same temperature for another 3 hours.
Next, the temperature was reduced to 80 ± 5 ° C., and the mixture was treated for 1 hour under a reduced pressure of 100 mmHg or less while blowing nitrogen gas.
The remaining unreacted oxirane was removed. Then, the inside of the system was returned to normal pressure with nitrogen gas, 20 g of the sample was withdrawn as an analysis sample, and the entire remaining amount was withdrawn into a 5-liter four-necked flask. The obtained reaction solution was 2544 g.

A stirrer, a nitrogen blowing tube, a thermometer and a vacuum joint were attached to the four-necked flask, and BHT was used.
(Reagent, manufactured by Kanto Chemical) 0.25 g (9
8 ppm) and stirred until completely dissolved.
The pH was adjusted to 2.3 using 7.5% hydrochloric acid. While blowing in nitrogen gas, the mixture was stirred for 1 hour while maintaining the temperature at 60 ± 2 ° C. Then, the temperature was raised to 100 ± 5 ° C., and vacuum was started while blowing nitrogen gas.
Dehydration was continued for another 2 hours after the temperature became lower than mHg. Next, 25.4 g (1% by weight based on the reaction solution) of Kyoward 1000 (trade name, manufactured by Kyowa Chemical Industry Co., Ltd.) as an acid adsorbent was added, and 80 ± 5 ° C., 1
After stirring for 1 hour under the condition of 00 mmHg or less,
The by-product salt and adsorbent are removed by filtration under reduced pressure, and 2
469 g of oligoalkyloxirane derivative was obtained (p
H6.8).

The polydispersity of the compound obtained by GPC is
1.028. The hydroxyl value of the obtained compound was 268.7, and the degree of unsaturation was 0.00. The cloud point of the 50% aqueous solution was 68.7 ° C. The molecular weight determined from the hydroxyl value was 835.1. When the number of moles of oxirane added was determined from the molecular weight obtained here and the molecular weight determined after the addition of ethyloxirane, 2 moles of oxirane had been added in total.

Therefore, the structure of the obtained oligoalkyloxirane derivative can be estimated to be the following formula (4).

[0064]

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Example 3 Diglycerin 498 was placed in a 5-liter autoclave equipped with a nitrogen blowing tube, an injection tube, a stirrer, and a thermometer.
g (3 moles) and 8.1 g of sodium methylate (0.
15 mol → 5 mol% based on glycerin), and a dealcoholization treatment was carried out for 1 hour at 80 ± 5 ° C. while stirring under a vacuum condition of 50 mmHg or less while blowing nitrogen gas. Then, the inside of the reaction system was
/ Cm ² (gauge pressure).
50.4 g (13.2 mol) of methyl oxirane 114
8.4 g (19.8 moles) of the mixture were pressured to 3.5 k
g / cm ² or less while controlling
The pressure was gradually increased at 0 ± 5 ° C. After injecting the whole amount, stirring was continued at the same temperature for another 5 hours. Then, the temperature was lowered to 80 ± 5 ° C., and the mixture was treated under a reduced pressure of 100 mmHg or less for 1 hour while blowing nitrogen gas to remove remaining unreacted methyloxirane and ethyloxirane. Then, the inside of the system was returned to normal pressure with nitrogen gas, and the whole amount was withdrawn to a 5-liter four-necked flask. The obtained reaction solution was 2545 g.

17. A stirrer, a nitrogen blowing tube, a thermometer, and a vacuum joint were attached to the four-necked flask.
The pH was adjusted to 2.7 using 5% hydrochloric acid. Temperature 10
While maintaining the temperature at 0 ± 2 ° C., vacuum was started while blowing nitrogen gas, and dehydration was continued for another 2 hours after the degree of vacuum became 50 mmHg or less. The by-produced salt and adsorbent were removed by filtration under reduced pressure to obtain 2493 g of the compound (pH
7.0).

The resulting poly (alkylalkyloxirane) derivative had a polydispersity of 1.028 and a hydroxyl value of 279.8.
And the degree of unsaturation was 0.01. The 50% aqueous solution had a cloud point of 62.7 ° C. The molecular weight determined from the hydroxyl value was 802. From this, the number of moles of methyl oxirane and ethyl oxirane added was calculated from the mixing ratio.
Mole was added.

Therefore, the structure of the obtained oligoalkyloxirane derivative can be estimated to be the following formula (5).

[0069]

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{} Random addition

COMPARATIVE EXAMPLE 1 Synthesis was attempted by a method generally used industrially.
5 tubes equipped with nitrogen blowing pipe, injection pipe, stirrer, thermometer
664 g of diglycerin (4
6.4 g (0.16 mol →
(4 mol% based on glycerin) and 1% with nitrogen gas.
0kg / cm^TwoTo 2378 g of methyl oxirane
(41 mol) at a pressure of 5.0 kg / cm ^TwoBelow
And gradually press in at 130 ± 5 ℃
Was. After injecting the whole amount, stirring was continued at the same temperature for another 2 hours.
Then lower the temperature to 80 ± 5 ° C and do not blow nitrogen gas.
And then treated under reduced pressure of 100 mmHg or less for 1 hour.
The remaining unreacted methyloxirane was removed. Incidentally
The system is returned to normal pressure with elemental gas and the total volume is
I took it out to Suko. The obtained reaction solution weighed 2927 g.
Was.

Next, Kyoward 7 which is an alkali adsorbent
00 (manufactured by Kyowa Chemical Industry Co., Ltd.) was placed in a four-necked flask, and a stirrer, a nitrogen blowing tube, a thermometer, and a vacuum joint were attached. The temperature was raised to 90 ± 5 ° C., and vacuum was applied while blowing nitrogen gas. Start taking, vacuum degree is 200mmH
g, the adsorption treatment was continued for another hour. The adsorbent was removed by filtration under reduced pressure to obtain 2831 g of a compound (pH 6.9). FIG. 2 shows a chart of gel permeation chromatography (GPC) of the obtained oligoalkyloxirane derivative.

The polydispersity of the obtained compound was 1.052, the hydroxyl value was 317.1, and the degree of unsaturation was 0.1.
It was one. The 50% aqueous solution had a cloud point of 72.4 ° C. The molecular weight determined from the hydroxyl value was 707.7. From this, when the number of moles of methyloxylan is determined,
A total of 9.34 moles of methyl oxirane had been added.

Comparative Example 2 In the same manner as in Comparative Example 1, the addition mole of methyloxirane was
An attempt was made to synthesize a large number of samples. Nitrogen injection pipe, injection
5 liter auto with tube, stirrer and thermometer
In a clave, 332 g (2 mol) of diglycerin and water
4.0 g of sodium oxide (0.1 mol → based on glycerin)
5 mol%) and 1.0 kg / cm 2 with nitrogen gas. ^Two
And 2262 g (39 mol) of methyloxirane
Pressure is 5.0kg / cm^TwoControl to be
While gradually press-fitting at 130 ± 5 ° C. Full injection
Thereafter, stirring was continued at the same temperature for another 2 hours. Then the temperature
100m while lowering to 80 ± 5 ° C and blowing nitrogen gas
Treated for 1 hour under reduced pressure of mHg or less
The methyl oxirane was removed. Then in the system with nitrogen gas
To normal pressure and transfer the whole amount to a 5-liter four-necked flask.
Was. The obtained reaction solution was 2511.9 g.

A stirrer, a nitrogen blowing tube, a thermometer, and a vacuum joint were attached to the four-necked flask, and the pH was adjusted to 2.3 using 85% hydrochloric acid. 120 ± 5 temperature
℃, start vacuuming while blowing nitrogen gas,
After the degree of vacuum became 200 mmHg or less, dehydration was further continued for 1 hour. Remove by-product salts by vacuum filtration,
2430.1 g of the compound were obtained (pH 6.7).

The resulting compound had a polydispersity of 1.081, a hydroxyl value of 190.0 and an unsaturation of 0.1.
It was 7. The 50% aqueous solution had a cloud point of 23.1 ° C. The molecular weight determined from the hydroxyl value was 1181.1. When the number of moles of methyl oxirane was determined from this, methyl oxirane was added in a total of 17.5 moles.

Comparative Example 3 In the same manner as in Comparative Example 1, instead of alkyloxirane
Was synthesized using oxirane. Nitrogen injection pipe, injection
5 liter auto with tube, stirrer and thermometer
In a clave, 830 g (5 mol) of diglycerin and water
8.0 g of sodium oxide (0.2 mol → based on glycerin)
4 mol%), and add 1.0 kg / cm ^Two
And the pressure is increased to 2024 g (46 mol) of oxirane.
5.0kg / cm^TwoDo not control to
The pressure was gradually increased at 130 ± 5 ° C. After press-fitting the entire amount,
For 2 hours at the same temperature. Then raise the temperature to 80 ± 5
℃, while blowing nitrogen gas, 100mmHg or less
The mixture was treated under reduced pressure for 1 hour to remove residual unreacted oxygen.
The run was removed. Then return the inside of the system to normal pressure with nitrogen gas.
The amount was withdrawn into a 5-liter four-necked flask. Got
The reaction liquid was 2780.2 g.

Next, Kyoward 7 which is an alkali adsorbent
00 (manufactured by Kyowa Chemical Industry Co., Ltd.) was placed in a four-necked flask, and a stirrer, a nitrogen blowing tube, a thermometer, and a vacuum joint were attached. The temperature was raised to 90 ± 5 ° C., and vacuum was applied while blowing nitrogen gas. Start taking, vacuum is 200m
The adsorption treatment was further continued for 1 hour after the pressure became below mHg. The adsorbent was removed by vacuum filtration to obtain 2703.5 g.
(PH 7.4) was obtained.

The polydispersity of the obtained compound was 1.048,
The hydroxyl value is 402.8, and the cloud point of a 50% aqueous solution is
The cloud point was 97 ° C. or higher (no cloud point was observed even at the time of 97 ° C. A temperature rise above this point was impossible due to boiling of the measurement system). The molecular weight determined from the hydroxyl value was 557.1. When the number of moles of oxirane was determined from this, 8.9 moles of oxirane was added in total. The structural formula of this compound is represented by the following formula (6).

[0080]

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Examples 4 to 6 and Comparative Examples 4 to 10 A 10% aqueous solution was prepared using the compound of the present invention, and a sensory evaluation was made on the absence of stickiness (freshness) and moistness. Further, the compound of the present invention was stored at 50 ° C. for one week, and the change over time in odor was examined. The sensory evaluation was 1
0 specialized panelists were used. As for the evaluation method, the sample was applied after the upper arm was washed, and the absence of stickiness (freshness) and the moistness immediately after application and overnight were evaluated on a 5-point scale. The evaluation method followed the following criteria. Table 1 shows the total points for each item. 5: Good 4: Somewhat good 3: Normal 2: Somewhat bad 1: Bad

[0082]

[Table 1]

Example 7 A cleansing cream was prepared using the oligoalkyloxirane derivative of the present invention. That is, after the oil phase having the following composition was heated to 60 ° C. and uniformly dissolved, the aqueous phase was added at the same temperature while stirring. Sensory evaluation of the feeling of use of the obtained cleansing cream was performed. The formulation was stored at 50 ° C. for one week, and the change over time in odor was examined.

The sensory evaluation was carried out by five expert panelists, who evaluated the absence of stickiness at the time of use and after use (freshness) and the moistness after use and after one night. went. The evaluation method followed the following criteria. Table 2 shows the total points for each item. 5: Good 4: Somewhat good 3: Normal 2: Somewhat bad 1: Bad

[0085]

[Table 2]

Oil phase: Hexadecyl alcohol 2.0% by weight Beeswax 6.0% by weight Vaseline 5.0% by weight Squalane 30.0% by weight Isopropyl myristate 5.0% by weight Glycerin monostearate 2.0% by weight % Stearic acid 0.5% by weight Polyoxyethylene (60 mol) hydrogenated castor oil 1.5% by weight Perfume proper amount Preservative proper amount Aqueous phase part: 8.0% by weight of the compound of Example 3 Purified water balance

Example 8 A cleansing lotion was prepared using the compound of the present invention. That is, the oil phase portion having the following composition was heated to 60 ° C.
After heating and uniformly dissolving, the aqueous phase was added at the same temperature while stirring. The obtained cleansing lotion was evaluated in the same manner as in Example 7. Table 2 shows the results.

Oil phase: Hexadecyl alcohol 1.0% by weight Liquid paraffin 10.0% by weight Vaseline 2.0% by weight Glycerin monostearate 2.0% by weight Stearic acid 0.5% by weight Polyoxyethylene (60 mol ) Hardened castor oil 1.5% by weight Perfume proper amount Preservative proper amount Aqueous phase: Compound of Example 2 7.0% by weight Triethanolamine 0.5% by weight Purified water balance

Example 9 A hair treatment lotion was prepared using the compound of the present invention. That is, polyoxyethylene (60 mol) hydrogenated castor oil, perfume, stearyltrimethylammonium chloride, a preservative and the compound of Example 1 were added to ethanol at room temperature, and after uniform mixing, purified water was added.
The hair treatment lotion thus obtained was used in the same manner as in Example 7 to adjust the hair to use. Table 2 shows the results
Shown in

Compound of Example 1 10.0% by weight Ethanol 5.0% by weight Polyoxyethylene (60 mol) hydrogenated castor oil 0.2% by weight Stearyl trimethylammonium chloride 0.2% by weight Preservative proper amount Perfume proper amount Purification Water

Example 10 A hair styling foam was prepared in the same manner as in Example 9 using the compound of the present invention. The obtained hair styling foam was evaluated in the same manner as in Example 7. Table 2 shows the results. Compound of Example 2 15.0% by weight Ethanol 6.0% by weight Polyoxyethylene (40 mol) hydrogenated castor oil 0.2% by weight Polyoxyethylene (6 mol) sodium tridecyl ether acetate 0.5% by weight Preservative Appropriate amount Perfume Appropriate amount Liquefied petroleum gas 7.5% by weight Purified water

Example 11 A hair styling gel was prepared using the compound of the present invention. Table 2 shows the results. Compound of Example 2 18.0% by weight Ethanol 5.0% by weight Polyoxyethylene (60 mol) hydrogenated castor oil 0.2% by weight Carboxyvinyl polymer 0.5% by weight Preservative proper amount Perfume proper amount Purified water balance

Example 12 A sunscreen was prepared using the compounds of the present invention. The oil phase containing the emulsifier of the base having the following composition was heated to 60 ° C.
After heating and uniformly dissolving, the aqueous phase was added at the same temperature while stirring. Table 2 shows the results. Oil phase part: ethyl paraaminobenzoate 2.0% by weight 0.5% by weight of dimethylpolysiloxane 7.0% by weight of hexadecyl 2-ethylhexanoate 8.0% by weight of the compound of Example 3 Ethanol 15.0% by weight Polyoxy Ethylene (60 mol) hydrogenated castor oil 2.0% by weight Perfume proper amount Preservative proper amount Water phase part: purified water balance

Example 13 A body soap was prepared using the compound of the present invention.
After heating and dissolving the base having the following composition other than purified water at 50 ° C. with stirring, purified water was added at the same temperature with stirring. Table 2 shows the results. Polyoxyethylene (20 mol) dodecyl ether 10.0% by weight Sodium laurate 2.0% by weight Diethanolamide laurate 3.0% by weight Compound of Example 1 10.0% by weight Polyoxyethylene (80) sorbitan monolau Rate 5.0% by weight Preservatives qs Perfume qs Purified water balance

Comparative Example 11 A cleansing cream was prepared using the compound of Comparative Example 2 in place of the compound of Example 3 in the formulation shown in Example 7. Table 2 shows the results.

Comparative Example 12 A cleansing cream was prepared in the same manner as in Example 7, except that the compound of Comparative Example 1 was used instead of the compound of Example 3. Table 2 shows the results.

Comparative Example 13 A cleansing cream was prepared in the same manner as in Example 7, except that the compound of Example 3 was replaced with glycerin as a typical humectant. Table 2 shows the results.

Comparative Example 14 A hair treatment lotion was prepared in the same manner as in Example 9 except that the compound of Comparative Example 2 was used instead of the compound of Example 1. Table 2 shows the results.

Comparative Example 15 A hair styling gel was prepared in the same manner as in Example 11 except that glycerin, a typical humectant, was used instead of the compound of Example 2. Table 2 shows the results.

Comparative Example 16 A sunscreen was prepared by using the compound of Comparative Example 1 instead of the compound of Example 3 in the formulation shown in Example 12.
Table 2 shows the results.

Comparative Example 17 A cleansing cream was prepared in the same manner as in Example 7 except that the compound of Example 3 was used instead of the compound of Example 3. Table 2 shows the results.

[Brief description of the drawings]

FIG. 1 is a GPC chart of the oligoalkyloxirane derivative obtained in Example 1.

FIG. 2 is a GPC chart of the oligoalkyloxirane derivative obtained in Comparative Example 1.

 ──────────────────────────────────────────────────続 き Continuing on the front page F term (reference) 4C083 AC012 AC022 AC092 AC102 AC182 AC242 AC352 AC422 AC432 AC482 AC542 AC642 AC692 AD051 AD052 AD092 AD152 BB51 CC01 CC05 CC19 CC23 CC32 CC33 DD08 DD31 DD41 EE01 EE06 EE17 FF01 4J002 EJ02 CH031 EV036 FD076 GD03 4J005 AA04 AA07 BA00 BB02

Claims (6)

[Claims] The polydispersity represented by the formula (1) is 1.04 or less.
Below, and the cloud point of the 50% aqueous solution is 40-90 ° C.,
Oligoalkyloxy having an unsaturation degree of not more than 0.03
Silane derivatives. Embedded image(However, AO is -OCH_TwoCH (CH_Three) -Group or-
OCH_TwoCH (CH_TwoCH _Three)-Group, and EO is -OC
H_TwoCH_Two-AO and EO are randomly added
Or may be added in a block shape. l, m, n
And o is -OCH_TwoCH (CH_Three) -Group or -OCH
_TwoCH (CH_TwoCH_ThreeA), the average number of moles of the group
b, c and d are -OCH_TwoCH_Two-Average number of moles of group added
Where 1 ≦ l, m, n, o ≦ 4,0 ≦ a, b, c, d
≦ 3, 5 ≦ l + m + n + o ≦ 12, 0 ≦ a + b + c + d
It is a number that satisfies ≦ 4. ) 2. The method for producing an oligoalkyloxirane derivative according to claim 1, wherein the alcoholate catalyst represented by the formula (2) is used in an amount of 0.005 to 5 mol per mol of diglycerin.
0.1 mol, and after dealcoholation treatment under reduced pressure, alkyl oxirane or oxirane was added in 8 moles.
A method for producing an oligoalkyloxirane derivative, wherein the addition reaction is performed at 0 to 110 ° C. ROX (2) (where R is a linear or branched hydrocarbon group having 1 to 4 carbon atoms, and X is potassium or sodium) 3. The method for producing an oligoalkyloxirane derivative according to claim 1, wherein the alcoholate catalyst represented by the formula (2) is used in an amount of 0.005 to 5 mol per mol of diglycerin.
0.1 mol, and after dealcoholation treatment under reduced pressure, alkyl oxirane or oxirane was added in 8 moles.
Addition reaction is carried out at 0 to 110 ° C., and then the reaction solution is adjusted to pH 3 or less in the presence of an antioxidant, and then treated with an acid adsorbent containing an alkaline earth metal oxide or an alkaline earth metal hydroxide. A method for producing an oligoalkyl oxirane derivative, which comprises treating. ROX (2) (where R is a linear or branched hydrocarbon group having 1 to 4 carbon atoms, and X is potassium or sodium) 4. A humectant comprising the oligoalkyloxirane derivative according to claim 1. 5. A cosmetic comprising the oligoalkyloxirane derivative according to claim 1 in an amount of 2 to 40% by weight. 6. A detergent comprising the oligoalkyloxirane derivative according to claim 1 in an amount of 2 to 40% by weight.