JP6988628B2 - Alkylene oxide derivatives, cleansers, lubricants, wetting agents and skin cleansers compositions - Google Patents

Description

The present invention relates to novel alkylene oxide derivatives, cleansers, lubricants, wetting agents and skin cleansing compositions. Specifically, a novel alkylene oxide derivative that is liquid at room temperature, has high detergency against dirt components, has good lubricity, and has an excellent moisturizing effect, a detergent, a lubricant, and a wetting agent composed of the alkylene oxide derivative, and the alkylene oxide. The present invention relates to a skin cleansing composition containing a derivative.

There are various types of nonionic surfactants, one of which is an alkylene oxide derivative. The alkylene oxide derivative is a useful surfactant whose hydrophilicity, lipophilicity balance and molecular weight can be controlled by the number of added moles such as oxyethylene group and oxypropylene group. Among them, a pluronic surfactant having a polyoxypropylene group as a lipophilic group and a polyoxyethylene group as a hydrophilic group has a low critical micelle concentration, can be used even at a low concentration, and has low foaming properties. It is used in various industrial applications as an emulsifying solubilizer, wetting agent, penetrant, and lubricant.

In recent years, in the fields of pharmaceuticals, cosmetics, and toiletries, there is an increasing need to improve the detergency of stain components with water-based preparations, and in the lubricating oil field, there is a growing need to impart lubricity to water-based preparations with excellent cooling efficiency.
However, in order to improve the detergency and lubricity against dirt components by using the above-mentioned pluronic type surfactant, it is required to increase the molecular weight of the polyoxypropylene group which is a lipophilic group. On the other hand, in order to impart water solubility, it is necessary to increase the molecular weight of the polyoxyethylene group, which is a hydrophilic group, and since the polyoxyethylene group has high crystallinity, it is solid at room temperature. There was a problem that the activator had poor handleability.

In view of these circumstances, for example, in Patent Document 1, a base oil for a lubricating oil in which an oxyethylene group and a tetramethylene glycol group are randomly introduced into a polyhydric alcohol is liquid at room temperature and has excellent water solubility and lubricity. As disclosed, this compound has insufficient detergency against dirt components.

Further, Patent Document 2 discloses a fermentation defoaming agent in which a polyoxypropylene group is introduced into a mixture of a fat and oil and a polyhydric alcohol, and then an oxypropylene group and an oxyethylene group are randomly introduced. However, although this compound is liquid at room temperature and has an excellent defoaming effect, it has a problem that it is difficult to apply to an aqueous formulation due to insufficient water solubility and insufficient wettability, which is an essential function as a surfactant. There was a problem that it was.

On the other hand, as a surfactant that is liquid at room temperature and has excellent low foaming properties and wettability, an alkylene oxide adduct in which a polyoxypropylene group is introduced into a hydrocarbon group and then an oxyethylene group and an oxypropylene group are randomly introduced. Is also disclosed (Patent Document 3). It is described in Patent Document 3 that this surfactant has good fluidity at a low temperature and is excellent in low foaming property and defoaming property, but the lubricity is not sufficiently satisfactory.

As described above, no alkylene oxide derivative which is liquid at room temperature, has high detergency against dirt components, has good lubricity, and has an excellent wetting effect has not been disclosed in any patent document.

On the other hand, when the stain component is washed with an aqueous preparation, the detergency against the stain component can be improved by using a surfactant having high detergency and wettability. However, in the case of skin cleansers that cleanse the skin, such as facial cleansers and makeup removers, if a high amount of surfactant is added to improve the cleansing power, irritation to the skin (tingling sensation) may occur. There was a problem that stickiness occurred.

In view of these circumstances, for example, Patent Document 4 discloses a skin cleansing agent containing a block polymer of a polyoxyethylene group and a polyoxypropylene group or a random polymer. This skin cleansing agent has a high cosmetic-removing effect, is easy to wash off, and is excellent in usability and safety. In the case of containing, there is a problem that the detergency is insufficient with the aqueous preparation.

Japanese Unexamined Patent Publication No. 2012-214706 Japanese Unexamined Patent Publication No. 2001-178446 Japanese Unexamined Patent Publication No. 2014-240378 Japanese Patent Application Laid-Open No. 2003-221310

As described above, an object of the present invention is to provide an alkylene oxide derivative having high detergency against dirt components, good lubricity, excellent moisturizing effect, room temperature liquid and excellent handleability.
Another object of the present invention is a detergent for cleaning stain components such as oils and fats and cosmetics, a lubricant for reducing friction between solids in contact with each other, and a solid by changing the interfacial tension between a solid and a liquid. It is an object of the present invention to provide a wetting agent having an action of making a surface easy to get wet.
Furthermore, another object of the present invention is to provide a skin cleansing composition such as a cleanser and a make-up remover (cleansing).

As a result of diligent studies to solve the above problems, the present inventors have found that an alkylene oxide derivative having a specific structure can solve the above problems, and have completed the present invention. The present invention is as follows.

That is, the present invention is an alkylene oxide derivative represented by the following formula (I).
Y- {O- (AO) _g -[(PO) _h / (EO) _k ] -H} _m ... (I)
(Y is a residue of a compound having 2 to 9 hydroxyl groups excluding hydroxyl groups, AO is an oxyalkylene group having 3 carbon atoms, PO is an oxypropylene group, and EO is an oxyethylene group. G, h, k Is the average number of moles of the oxyalkylene group, the oxypropylene group, and the oxyethylene group, respectively, 1 ≦ g ≦ 50, 1 ≦ h ≦ 50, 1 ≦ k ≦ 150, (g + h + k) ≧ 10, and 0.2. ≦ g / (h + k) ≦ 2.0. [(PO) _h / (EO) _k ] indicates a polyoxyalkylene group formed by randomly adding h mol of PO and k mol of EO, and has a random rate z. Is 0.1 ≦ z <1.)

Further, the present invention is a cleaning agent made of the alkylene oxide derivative of the present invention; a lubricant made of the alkylene oxide derivative of the present invention: a wetting agent made of the alkylene oxide derivative of the present invention.

Further, the present invention is a skin cleansing composition containing 0.5 to 20% by mass of the alkylene oxide derivative of the present invention.

The alkylene oxide derivative of the present invention has high detergency against dirt components, good lubricity, excellent wet penetration effect, and is excellent in handling at room temperature.
According to the cleaning agent made of the alkylene oxide derivative of the present invention, it is possible to clean stain components such as oils and fats and cosmetics with high detergency.
According to the lubricant composed of the alkylene oxide derivative of the present invention, the coefficient of friction between the adhering solids can be reduced.
According to the wetting agent composed of the alkylene oxide derivative of the present invention, the surface wettability to various solids such as glass, metal and resin can be improved.
According to the skin cleansing composition containing a predetermined amount of the alkylene oxide derivative of the present invention, the effects of high detergency, no stickiness, and less irritation (tingling sensation) can be obtained.
In the present invention, "room temperature liquid" means that the product is in a liquid state at 25 ° C.

Hereinafter, the alkylene oxide derivative, the cleansing agent, the lubricant, the wetting agent, and the skin cleansing agent composition of the present invention will be sequentially described.

<alkylene oxide derivative>
The alkylene oxide derivative of the present invention is represented by the following formula (I).
Y- {O- (AO) _g -[(PO) _h / (EO) _k ] -H} _m ... (I)

Y is a residue having 2 or more carbon atoms and having 2 to 9 hydroxyl groups excluding all hydroxyl groups, and m is 2 to 9 in the number of hydroxyl groups of the Y compound.
Compounds having 2 to 9 hydroxyl groups include ethylene glycol, propylene glycol and hexylene glycol when m = 2, glycerin and trimethylolpropane when m = 3, and erythritol and pentaerythritol when m = 4. , Sorbitol, diglycerin, alkylglycoside, xylitol if m = 5, dipentaerythritol, sorbitol, inositol if m = 6, sucrose, trehalose if m = 8, maltitol if m = 9. And so on. Further, a mixture of these compounds may be used as the compound having 2 to 9 hydroxyl groups.
m is preferably 2 to 6, and particularly preferably 2 to 3. When m is 1, the lubricity may decrease. Further, when m is 10 or more, the detergency and the wetting effect may decrease.

AO is an oxyalkylene group having 3 or 4 carbon atoms, and examples thereof include an oxypropylene group, an oxyisobutylene group, an oxy1-ethylethylene group, an oxy2-butylene group, and an oxytetramethylene group.
When the average number of moles of substance g of AO is 2 or more, the AO of 2 or more may be a group of the same kind or a group of different kinds. When AO is two or more different types of groups, it may be either random addition or block addition.
As the AO, an oxypropylene group having 3 carbon atoms is preferable.

PO is an oxypropylene group and EO is an oxyethylene group. G, h, and k in the formula (I) are the average number of moles of substance added per molecule of AO, PO, and EO, respectively.

g is 1 to 50, preferably 5 to 30, and particularly preferably 10 to 20. If g is 0, the detergency is reduced, and if g is too large, the wetting effect may be reduced.

h is 1 to 50, preferably 3 to 30, and particularly preferably 4 to 20. When h is 0, it becomes solid at room temperature and the handleability may be deteriorated, and when h is too large, the detergency may be deteriorated.

k is 1 to 150, preferably 5 to 60, and particularly preferably 10 to 30. When k is 0, the water solubility may be impaired or the detergency and moisturizing effect may be deteriorated. I have something to do.

(G + h + k) is 10 or more, preferably 15 or more, and particularly preferably 20 or more. If (g + h + k) is less than 10, the detergency and lubricity may decrease. The upper limit of (g + h + k) is preferably 200, particularly preferably 150, and even more preferably 100.
Further, [g / (h + k)] is 0.2 or more and 2.0 or less, preferably 0.3 or more and 1.5 or less, and particularly preferably 0.4 or more and 1.0 or less. If [g / (h + k)] is less than 0.2, the detergency and lubricity may be lowered, and if it is more than 2.0, the wetting effect may be lowered or the water solubility may be impaired.

The binding portion of EO and PO in formula (I) _{is described as [(PO) h} / (EO) _k ], and this description is that h mol PO and k mol EO are not block-like but random in the present invention. It shows that they are connected in a shape. When EO and PO are bonded in a block shape, they become solid at room temperature, which may reduce the wetting effect and lubricity.

The alkylene oxide derivative represented by the formula (I) of the present invention has a random rate of 0.1 ≦ z <1, preferably 0.2 ≦ z <1, and particularly preferably 0.3 ≦ z. ≦ 0.95, more preferably 0.4 ≦ z ≦ 0.90.
If the random rate z is too small, the solid property may be exhibited at room temperature, the handleability may be deteriorated, or the wetting effect may be deteriorated.

The random rate in the alkylene oxide derivative represented by the formula (I) is obtained from the average addition moles g, h, k per molecule of AO, PO, and EO in the formula (I) according to the following formula (II). Can be asked.

z = (h + k) / (g + h + k) (II)

The alkylene oxide derivative represented by the formula (I) of the present invention can be produced by a known method. For example, after addition polymerization of alkylene oxide to polyhydric alcohol at 50-160 ° C. and 0.5 MPa (gauge pressure) or less under an alkaline catalyst, addition polymerization of a mixture of ethylene oxide and propylene oxide is carried out, and hydrochloric acid, phosphoric acid and acetic acid are added. It can be obtained by neutralizing with an acid such as, and further removing water and a neutralizing salt.

<Cleaning agent>
The detergent of the present invention comprises an alkylene oxide derivative represented by the formula (I) of the present invention.
The detergent of the present invention can be used as a preparation in which the alkylene oxide derivative represented by the formula (I) is dissolved in an aqueous component. Examples of the aqueous component include water; lower alcohols such as ethyl alcohol and propyl alcohol; and a mixed solution of water and lower alcohol, and water is preferable among these.
The content of the alkylene oxide derivative in the detergent of the present invention is preferably 0.1 to 10% by mass, particularly preferably 0.5 to 8% by mass, and further preferably 1 to 5% by mass. When the content of the alkylene oxide derivative is in the above range, the detergency can be improved.

The cleaning target of the cleaning agent of the present invention is a stain component that does not dissolve in or is difficult to dissolve in the above-mentioned aqueous component. Examples of such stain components include fats and oils such as beef tallow oil and soybean oil; and oily components such as fragrances, unsaturated compounds, and saturated compounds.

The cleaning agent of the present invention may contain a component generally used for the cleaning agent as another optional component.

<Lubricant>
The lubricant of the present invention comprises an alkylene oxide derivative represented by the formula (I) of the present invention.
The lubricant of the present invention can be used as a preparation in which the alkylene oxide derivative represented by the formula (I) is dissolved in an aqueous component. Examples of the aqueous component include the above-mentioned aqueous components, and among these, water is preferable.
The content of the alkylene oxide derivative in the lubricant of the present invention is preferably 0.1 to 10% by mass, particularly preferably 0.5 to 8% by mass, and further preferably 1 to 5% by mass. When the content of the alkylene oxide derivative is within the above range, foaming is less likely to occur and the lubricity can be improved.
The lubricant of the present invention may contain a component generally used for the lubricant as another optional component.

<Wetting agent>
The wetting agent of the present invention comprises an alkylene oxide derivative represented by the formula (I) of the present invention.
The wetting agent of the present invention can be used as a preparation in which the alkylene oxide derivative represented by the formula (I) is dissolved in an aqueous component. Examples of the aqueous component include the above-mentioned aqueous components, and among these, water is preferable.
The content of the alkylene oxide derivative in the wetting agent of the present invention is preferably 0.1 to 10% by mass, particularly preferably 0.5 to 8% by mass, and further preferably 1 to 5% by mass. When the content of the alkylene oxide derivative is within the above range, foaming is less likely to occur and the wettability can be improved.
The wetting agent of the present invention may contain a component generally used for the wetting agent as another optional component.

<Skin cleansing composition>
The skin cleansing composition of the present invention contains the alkylene oxide derivative represented by the formula (I) of the present invention, and further contains at least the above-mentioned aqueous component.
The skin cleansing composition of the present invention can be used for the purpose of cleaning the skin (skin), and has the effect that irritation (tingling sensation) to the skin (skin) is less likely to occur and stickiness is less likely to occur. Therefore, the skin cleansing composition of the present invention can be safely used for a site where skin disorders such as inflammation and heat rash have developed, and a sensitive site such as a delicate zone, and is used for cleaning sensitive areas of the skin. It can be suitably used as an agent composition, for example, as a detergent composition for a delicate zone.

The content of the alkylene oxide derivative in the skin cleansing composition of the present invention is 0.5 to 20% by mass, preferably 1 to 10% by mass, particularly preferably 1.5 to 8% by mass, still more preferably 2. ~ 5% by mass. If the content of the alkylene oxide derivative is too low, the detergency against dirt components such as oily components may be insufficient, and conversely, if this content is too high, stickiness and tingling sensation may occur during application. be.
The skin cleansing composition of the present invention may contain an ingredient generally used in cosmetics as another optional ingredient.

Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples. The following "%" means "mass%" unless otherwise specified.

<Examples 1 to 6, Reference Example 1 and Comparative Examples 1 to 5>
[Synthesis Example 1: Synthesis of Compound 1]
50 g of propylene glycol and 3.2 g of potassium hydroxide as a catalyst were charged in the autoclave, the air in the autoclave was replaced with dry nitrogen, and then the catalyst was dissolved at 140 ° C. with stirring. Subsequently, 1200 g of propylene oxide was added dropwise at 120 ° C. and 0.2 to 0.5 MPa (gauge pressure) using a dropping device, and the mixture was stirred for 3 hours. Subsequently, a mixture of 1578 g of ethylene oxide and 400 g of propylene oxide was added dropwise from a dropping device at 120 ° C. and 0.2 to 0.5 MPa (gauge pressure), and the mixture was stirred for 2 hours. Then, the reaction composition was taken out from the autoclave, neutralized with hydrochloric acid to adjust the pH to 6 to 7, and removed by treating at 100 ° C. for 1 hour at a reduced pressure of −0.095 MPa (gauge pressure) in order to remove the contained water. .. Further, filtration was performed to remove the salt produced after the treatment to obtain Compound 1.
Further, the number average molecular weights of ethylene oxide and propylene oxide adduct were obtained from the hydroxyl value obtained by the hydroxyl value measurement according to JIS K1557-1, and the values of g, h, and k in the formula (I) were specified from the number average molecular weight.

[Synthesis Example 2: Synthesis of Compounds 2 to 10 and 12]
An alkylene oxide derivative was obtained as compound 2 by the same method as in Synthesis Example 1 except that the starting material and the addition amounts of ethylene oxide and propylene oxide were changed and 1,2-butylene oxide was used as the alkylene oxide. .. Compounds 3 to 10 and 12 were synthesized by the same synthesis method. Types of starting material and alkylene oxide, number of hydroxyl groups m, average number of moles of substance added (g, h, k) of alkylene oxide, ethylene oxide and propylene oxide, total number of moles of substance added (g + h + k), [g / (h + k) )], And the random rate z are shown in Table 1. In addition, the compounds 11 used in the following comparative examples are also shown in Table 1.

Using the above compounds 1 to 12, Examples 1 to 6, Reference Examples 1 and Comparative Examples 1 to 5 were used, and the detergency, lubricity, and wetting effect were evaluated. The results of detergency are summarized in Table 2, the results of lubricity are summarized in Table 3, and the results of moisturizing effect are summarized in Table 4. The freezing points of the above compounds 1 to 12 are also shown in Tables 2 to 4. The freezing point was measured by a method according to JISK-0065-1992.

(A) Detergency In order to evaluate the detergency of the compounds of Examples 1 to 6, Reference Examples 1 and Comparative Examples 1 to 5 as a detergency, a 5% aqueous solution of each compound was used. The detergency test was carried out according to the Leenut improved detergency test method (JIS 3370 4.9). After washing at 25 ° C. for 3 minutes, rinsing was performed for 1 minute, and the washing rate (%) was calculated from the weight before and after washing by the following formula, and the washing power was evaluated.
In addition, beef tallow (10 g), soybean oil (10 g), glyceryl monooleate (0.25 g), and Sudan III (0.1 g) dissolved in 60 ml of chloroform were used as artificial stains.
Cleaning rate (%) = {(Weight of slide glass after cleaning)-(Weight of slide glass before adhesion of stains)} / (Amount of stains attached)
Detergency was evaluated according to the following criteria.
⊚: Strong detergency (cleaning rate 70% or more).
◯: Detergency is slightly high (cleaning rate 60% or more and less than 70%).
Δ: Detergency is slightly weak (cleaning rate 50% or more and less than 60%).
X: Detergency is weak (cleaning rate is less than 50%).

(B) Lubricity In order to evaluate the lubricity of the compounds of Examples 1 to 6, Reference Examples 1 and Comparative Examples 1 to 5 as a lubricant, a 5% aqueous solution of each compound was used. The lubricity test was performed using an SRV Lubricant and Material Test System (manufactured by OPTIMOL). The test was carried out with a ball / disc, and each test piece was made of SUJ-2. The test conditions were a temperature of 40 ° C., a load of 40 N, an amplitude of 1 mm, a frequency of 50 Hz, and a friction coefficient (μ) was measured using a 5% aqueous solution of an alkylene oxide derivative. For each lubricity, the lubricity was evaluated according to the following evaluation criteria.
⊚: The coefficient of friction (μ) is 0.11 or less.
◯: The coefficient of friction (μ) is larger than 0.11 and 0.12 or less.
Δ: The coefficient of friction (μ) is larger than 0.12 and 0.13 or less.
X: The coefficient of friction (μ) is larger than 0.13.

(C) Wetting effect In order to evaluate the wetting power of the compounds of Examples 1 to 6, Reference Examples 1 and Comparative Examples 1 to 4 as a wetting agent, a 5% aqueous solution of each compound was used and a glass plate (MICRO SLIDE) was used. GLASS, Matsunami Glass Industry Co., Ltd.), Cold rolled steel sheet (SPCC-SD, JIS G3141), Artificial leather (Suprale PBZ13001, Ideatex Japan Co., Ltd.) Contact angle (Measuring device: Kyowa Surface Science Co., Ltd., Drop Master) Series, DM-501) was measured. The test solution was filled in a glass syringe equipped with a Teflon-coated needle 18G, the droplet volume was adjusted to 2.0 μL, and the contact angle was measured 10 seconds after the droplet was applied.
It was decided that the measurement was performed 5 times per sample and the average value was used as the value of the contact angle. With the contact angle of water as a blank, the contact angles of each compound (5% aqueous solution) with respect to various substrates were compared, and the reduction rate of the contact angle was calculated by the following formula. The evaluation was performed according to the following criteria.
Contact angle reduction rate (%) = {1- (contact angle of test compound) / (contact angle of blank)} × 100
⊚: The reduction rate of the contact angle is 25% or more for any of the base materials.
◯: The contact angle reduction rate is 15% or more and less than 25% for any of the base materials.
Δ: The contact angle reduction rate with respect to any substrate is less than 15%.
X: The contact angle reduction rate for all the substrates is less than 15%.

As is clear from Tables 2 to 4, all of the compounds 1 , 3 to 7 used in Examples 1 to 6 have a freezing point of 9 ° C. or lower, so that they are liquid at room temperature and have good handleability. In addition, the cleaning agents, lubricants, and wetting agents of Examples 1 and 3 to 7 all had excellent performance.

On the other hand, as is clear from Tables 2 to 4, in Comparative Examples 1 to 5 using compounds 8 to 12 which do not correspond to the alkylene oxide derivative of the present invention, they are liquid at room temperature and have detergency against stain components. None of them satisfied all of high, good lubricity, and excellent moisturizing effect.

<Examples 7 to 9, Reference Examples 2 to 3 and Comparative Examples 6 to 8>
The compounds 1 to 3, 8 and 9 shown in Table 1 and the components shown in Table 5 were mixed at room temperature so as to have the ratio shown in Table 5 until they became uniform to prepare a skin cleansing composition.

<Evaluation of skin cleansing composition>
A usability test was conducted by 10 specialized panelists. Take the prepared skin cleansing composition on cotton and have the makeup removed, and each panelist will explain the following 1) cleansing effect, 2) no stickiness during washing, and 3) tingling sensation after washing. The evaluation was made on a 4-point scale and a score was given.

1) Cleaning effect The makeup was removed with cotton, and its cleansing effect was evaluated according to the following criteria. The average score of the evaluation of 10 panelists was 3.0 or higher.
4 points: Makeup removes very well, and you can feel a sufficient cleansing effect.
3 points: Makeup is easy to remove and you can feel the cleansing effect.
2 points: Makeup does not come off very well, and you cannot really feel the cleansing effect.
1 point: Makeup hardly comes off and I can't feel the cleansing effect at all.

2) No stickiness The stickiness while removing makeup with cotton was evaluated according to the following criteria. "◎" and "○" were accepted.
⊚: Of the 10 respondents, 9 or more answered that they did not feel sticky.
◯: Of the 10 respondents, 7 to 8 responded that they did not feel sticky.
Δ: 5 to 6 out of 10 responded that there was no sticky feeling.
×: Of the 10 respondents, 4 or less answered that they did not feel sticky.

3) Tingling sensation after washing 10 panelists occluded and applied 50 μL of each skin cleansing composition of Examples and Comparative Examples to the forearm for 30 minutes. The stinging pain felt in the affixed part within 30 minutes was evaluated as stinging according to the following evaluation criteria, and a score was given. The average evaluation of 10 panelists was 2.0 or more as "○" (good), 1.0 or more and less than 2.0 as "△" (normal), and less than 1.0 as "x" (bad). .. However, if two or more panelists gave a score of 0, it was marked as "x" (defective).
3 points: I did not feel any numbness in the sticking part.
1 point: I felt a slight numbness in the affixed part.
0 points: I clearly felt a stinging pain in the affixed part.

As is clear from Table 5, in Examples 7 to 9 using the compound 1 or 3 corresponding to the alkylene oxide derivative of the present invention, 1) cleaning effect, 2) no stickiness during washing, and 3) after washing. All of the tingling sensations were good or passed.

On the other hand, in Comparative Examples 6 to 8 containing no alkylene oxide derivative of the present invention, 1) cleaning effect, 2) no sticky feeling during washing, and 3) tingling feeling after washing were all evaluated as good or acceptable. There was nothing that was.

Claims (5)

An alkylene oxide derivative represented by the following formula (I).
Y- {O- (AO) _g -[(PO) _h / (EO) _k ] -H} _m ... (I)
(Y is a residue of a compound having 2 to 9 hydroxyl groups excluding hydroxyl groups, AO is an oxyalkylene group having 3 carbon atoms, PO is an oxypropylene group, and EO is an oxyethylene group. G, h, k Is the average number of moles of the oxyalkylene group, the oxypropylene group, and the oxyethylene group, respectively, 1 ≦ g ≦ 50, 1 ≦ h ≦ 50, 1 ≦ k ≦ 150, (g + h + k) ≧ 10, and 0.2. ≦ g / (h + k) ≦ 2.0. [(PO) h / (EO) k] indicates a polyoxyalkylene group formed by randomly adding h mol of PO and k mol of EO, and has a random rate z. Is 0.1 ≦ z <1.) A cleaning agent comprising the alkylene oxide derivative according to claim 1. A lubricant comprising the alkylene oxide derivative according to claim 1. A wetting agent comprising the alkylene oxide derivative according to claim 1. A skin cleansing composition containing 0.5 to 20% by mass of the alkylene oxide derivative according to claim 1.