JP2000044505A - Polyether and its production - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a polyether that has a specific polyoxy-alkylene chain and shows excellent lubricity and its production process. SOLUTION: This polyether has two or more different groups that are prepared by randomly adding 2 or more kinds of alkylene oxides to an active hydrogen-bearing compound and has mixed polyoxyalkylene chains comprising structures that have mutually different mixing ratios of alkylene oxide between these groups; or has a single mixed polyoxyalkylene chain of a structure that has 2 or more kinds of alkylene oxides are randomly added and their mixing ratio of these alkylene oxides changes continuously.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a novel polyether.

[0002]

2. Description of the Related Art In the fields of metal working oils, hydraulic oils and the like, water-based lubricating oils are widely used for the purpose of preventing leakage of lubricating oil, generation of heat, and prevention of fire due to scattering. In aqueous lubricating oils represented by solution-type cutting oils and water-glycol hydraulic oils, polyether compounds are used as lubricity improvers and thickeners. A water-based lubricant containing a polyether compound has advantages in that it has a transparent appearance, is nonflammable, has high stability at high temperatures, and has no fear of separation or decay. The polyether compounds conventionally used for such purposes are often random polymers of ethylene oxide and propylene oxide. Recently, there is an example in which a block polymer of ethylene oxide and propylene oxide is used as a low-foaming polyether compound. For example, JP-A-8-231977 discloses a metalworking oil composition using a so-called reverse block type polyether obtained by adding propylene oxide to polyethylene glycol. JP-A-8-239683 discloses a block-type polyoxyalkylene compound having a PO-EO-PO structure (where PO represents an oxypropylene group and EO represents an oxyethylene group) and a fatty acid having 8 to 10 carbon atoms. And a water-soluble cutting oil composition containing a basic compound.

[0003]

However, all of these conventionally used polyether compounds have the disadvantage of poor lubricity. For example, a water-glycol hydraulic oil using a conventional polyether compound has excellent sliding lubrication, but is not satisfactory in rolling lubrication, and has a longer rolling bearing life than a mineral oil hydraulic oil. Troubles such as damage to the bearings due to a drop in the bearing were likely to occur. Accordingly, an object of the present invention is to provide a polyether having a specific polyoxyalkylene chain and excellent lubricity, and a method for producing the same.

[0004]

That is, the present invention provides an active hydrogen-containing compound having two or more different groups in which two or more alkylene oxides are randomly added, and an alkylene oxide between these groups. Having a mixed polyoxyalkylene chain having a structure in which the mixing ratio of oxides is different from each other; or a structure in which two or more alkylene oxides are added at random and the mixing ratio of these alkylene oxides changes continuously. A polyether having a single mixed polyoxyalkylene chain, a method for producing the same, and a lubricant comprising the polyether. More specifically, the present invention provides
A polyether compound having a mixed polyoxyalkylene chain obtained by randomly adding a mixed alkylene oxide obtained by mixing two or more alkylene oxides to an active hydrogen-containing compound, wherein a part of the mixed polyoxyalkylene chain or Polyethers characterized in that all are polyoxyalkylene chains formed by an addition method in which the mixing ratio in the mixed alkylene oxide changes stepwise or continuously as the addition reaction of the mixed alkylene oxide proceeds, and production thereof. Is the way.

[0005]

DETAILED DESCRIPTION OF THE INVENTION The polyether of the present invention is a polyether compound having a mixed polyoxyalkylene chain obtained by randomly adding a mixed alkylene oxide obtained by mixing two or more alkylene oxides to an active hydrogen-containing compound. It is. Examples of the active hydrogen-containing compound include a monol, a polyol, a carboxylic acid, and an amine.

Examples of the monol include methanol, ethanol, propanol, 2-propanol, butanol, 2-butanol, pentanol, 2-pentanol, 3-pentanol, isopentyl alcohol,
2-methyl-4-pentanol, hexanol, secondary hexanol, isohexanol, heptanol, secondary heptanol, octanol, 2-ethylhexanol,
Secondary octanol, isooctanol, nonanol, 2
Grade nonanol, 1-decanol, isodecyl alcohol, secondary decanol, undecanol, secondary undecanol, 2-methyldecanol, lauryl alcohol, 2
Grade dodecanol, 1-tridecanol, isotridecyl alcohol, secondary tridecanol, myristyl alcohol, secondary tetradecanol, pentadecanol, secondary pentadecanol, cetyl alcohol, palmityl alcohol, secondary hexadecanol, heptadeca Nol, secondary heptadecanol, stearyl alcohol, isostearyl alcohol, secondary octadecyl alcohol, oleyl alcohol, behenyl alcohol, eicosanol,
Docosanol, tetracosanol, hexacosanol,
Octacosanol, myristyl alcohol, rasserol, tetratriacontanol, allyl alcohol, cyclopentanol, cyclohexanol, 2-butyloctanol, 2-butyldecanol, 2-hexyloctanol, 2-hexyldecanol, 2-hexyldecanol, 2-octyldecanol, 2-octyldodecanol, 2-octyltetradecanol, 2-decyldodecanol, 2-decyltetradecanol, 2-decylhexadecanol, 2-dodecyltetradecanol,
Alcohols such as 2-dodecylhexadecanol, 2-dodecyloctadecanol, 2-tetradecyloctadecanol, 2-tetradecylicodecanol, 2-hexadecyloctadecanol and 2-hexadecylicosanol; phenol , Cresol, ethylphenol, tert-butylphenol, hexylphenol, octylphenol, nonylphenol, decylphenol,
Undecylphenol, dodecylphenol, tridecylphenol, tetradecylphenol, phenylphenol, benzylphenol, styrenated phenol,
Phenols such as p-cumylphenol are exemplified.

Examples of the polyol include ethylene glycol, propylene glycol, 1,4-butanediol, 1,2-butanediol, neopentyl glycol, 1,6-hexanediol, 1,2-octanediol, and 1,8-octanediol. Octanediol, isoprene glycol, 3-methyl-1,5-pentanediol, sorbite, catechol, resorcin, hydroquinone, bisphenol A, bisphenol F, hydrogenated bisphenol A,
Diols such as hydrogenated bisphenol F and dimer diol;

[0008] Trioxyisobutane, 1,2,3-butanetriol, 1,2,3-pentanetriol, 2-
Methyl-1,2,3-propanetriol, 2-methyl-2,3,4-butanetriol, 2-ethyl-1,
2,3-butanetriol, 2,3,4-pentanetriol, 2,3,4-hexanetriol, 4-propyl-3,4,5-heptanetriol, 2,4-dimethyl-2,3,4- Pentanetriol, glycerin, pentamethylglycerin, pentaglycerin, 1,2,4
Trihydric alcohols such as butanetriol, 1,2,4-pentanetriol, trimethylolethane, trimethylolpropane; pentaerythritol, erythritol, 1,2,3,4-pentanetetrol, 2,3
4,5-hexane tetrol, 1,2,4,5-pentane tetrol, 1,3,4,5-hexane tetrol,
4-hydric alcohols such as diglycerin and sorbitan; pentahydric alcohols such as adonitol, arabitol, xylitol and triglycerin;
Octahydric alcohols such as sucrose, polyglycerin and the like can be mentioned.

Examples of carboxylic acids include butyric acid, valeric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachinic acid, behenic acid, lignoceric acid, zomaric acid, oleic acid, Fatty acids such as linoleic acid, linolenic acid, gadrenic acid, erucic acid, ceracoleic acid, ricinoleic acid, hydroxystearic acid; oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacin Acid, undecandioic acid, dodecandioic acid, tridecandioic acid, tetradecandioic acid, cyclopentanedicarboxylic acid, hexahydrophthalic acid, methylhexahydrophthalic acid, dimer acid, phthalic acid, isophthalic acid, terephthalic acid, tolylene dicarboxylic acid , Xylylenedicarboxylic acid, male Acid, fumaric acid, itaconic acid, citraconic acid, mesaconic acid, tetrahydrophthalic acid, methyltetrahydrophthalic acid, nadic acid, methylnadic acid, methylbutenyltetrahydrophthalic acid, methylpentenyltetrahydrophthalic acid, trimellitic acid, pyromellitic acid And the like.

Examples of the amine include methylamine, ethylamine, propylamine, butylamine, octylamine, decylamine, dodecylamine, tridecylamine, cetylamine, cocoalkylamine, alkylamine derived from soybean oil, alkylamine derived from tallow, oleylamine, and stearyl. Alkylamines such as amines; monoethanolamine, diethanolamine, triethanolamine, N-methylmonoethanolamine, monoisopropanolamine, diisopropanolamine, triisopropanolamine, aminoethylethanolamine, 2-amino-2-methylpropanol, 2-amino-2-methyl-1,3-propanediol, aminoethylethanolamine, N, N, N ', N'-tetrakis (2-hydroxyethyl ) Ethylene diamine, N, N,
Alkanolamines such as N ′, N′-tetrakis (2-hydroxypropyl) ethylenediamine;

N-butyldiethanolamine, N-hexyldiethanolamine, N-octyldiethanolamine, N-decyldiethanolamine, N-cocoalkyldiethanolamine, alkyldiethanolamine from N-soy oil, alkyldiethanolamine from N-tallow, N-oleyldiethanolamine, N-butyldiethanolamine -Stearyldiethanolamine, N, N-dibutylethanolamine, N, N-dihexylethanolamine, N, N-dioctylethanolamine, N, N-didecylethanolamine, N, N-bis (cocoalkyl) ethanolamine, N-bis (alkyl derived from soybean oil) ethanolamine, N, N-bis (alkyl derived from tallow) ethanolamine, N-dioleylethanolamine, N-distearylethanol N- alkyl alkanol amines such as Min ethylenediamine, propylenediamine, butylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, polyamines such as pentaethylenehexamine.

The polyoxyalkylene chain in the polyether of the present invention is partially or wholly changed in the mixing ratio in the mixed alkylene oxide stepwise or continuously as the mixed alkylene oxide addition reaction proceeds. Is a polyoxyalkylene chain formed by Therefore,
The polyether according to the present invention may be a polyoxyalkylene compound in which two or more kinds of alkylene oxides are added in a random manner in part or all, and the mixing ratio is changed stepwise in two or more steps or continuously. It has an alkylene chain.

Examples of the alkylene oxide include ethylene oxide, propylene oxide, butylene oxide, styrene oxide, α-olefin oxide and the like. Among them, a mixed alkylene oxide of ethylene oxide and propylene oxide is practically useful. One of the above alkylene oxides is preferably ethylene oxide. The combination, ratio, order or the like of two or more alkylene oxides in the polyoxyalkylene chain is most suitable depending on the purpose of use of the polyether as long as it is within the range satisfying the conditions of the present invention described above. Can be arbitrarily selected and used.

A specific example of the method of adding an alkylene oxide to an active hydrogen-containing compound is the case where ethylene oxide and propylene oxide are added as alkylene oxides.

(1) At first, propylene oxide is independently added to the active hydrogen-containing compound, and then a mixed alkylene oxide of ethylene oxide and propylene oxide is added. Thereafter, as the addition reaction proceeds, ethylene oxide and propylene oxide are gradually added. A method in which the mixing ratio of the oxide is increased or decreased stepwise or continuously, or further changed in a manner such as increasing or decreasing the reverse thereafter, and added.

(2) First, a mixed alkylene oxide of ethylene oxide and propylene oxide is added to the active hydrogen-containing compound, and thereafter, the mixing ratio of ethylene oxide and propylene oxide is gradually or continuously increased as the addition reaction proceeds. A method of increasing or decreasing, and finally adding only ethylene oxide alone;

(3) First, a mixed alkylene oxide of ethylene oxide and propylene oxide is added to the active hydrogen-containing compound, and then the mixing ratio of ethylene oxide and propylene oxide is gradually or continuously increased as the addition reaction proceeds. , And once on the way,
A method in which only propylene oxide alone is added, and then the mixing ratio of ethylene oxide and propylene oxide is gradually or continuously changed as the addition reaction proceeds again.

In particular, when the polyether of the present invention is used as a lubricant, propylene oxide is first added alone to the active hydrogen-containing compound, and then a mixed alkylene oxide of ethylene oxide and propylene oxide is added. Thereafter, as the addition reaction proceeds, the mixture ratio of ethylene oxide and propylene oxide is gradually and continuously changed, and the mixture ratio is changed so that the mixture ratio of propylene oxide in the mixed alkylene oxide is reduced, and the mixture is obtained by adding. Polyether
It is preferable because it exhibits excellent lubricity.

The alkylene oxide to be first added to the active hydrogen-containing compound may be used alone or as a mixture, but a part or all of the final polyoxyalkylene chain is constituted by random polymerization of two or more mixed alkylene oxides. I have to. It is preferable to have a plurality of groups of random polymerization in which the mixing ratio of the mixed alkylene oxide is different. In addition, all parts of the polyoxyalkylene chain in the polyether of the present invention must not be in the form of a block-like adduct of two or more alkylene oxides, but some have homopolymerized parts. You may. For example, a so-called pluronic type polyether obtained by adding ethylene oxide to polypropylene glycol is not included in the present invention. The change in the mixing ratio of the mixed alkylene oxide often changes stepwise in a laboratory scale apparatus, but can be changed continuously in an industrial production scale.

The polyether of the present invention can be used in the same applications as conventional polyethers, but has excellent lubricating properties and is particularly suitable as a lubricant for hydraulic oils, metal working oils, cutting oils, fiber oils and the like. Can be used for Among the lubricants, water-based lubricants, especially hydrous hydraulic oils, metalworking oils,
It can be preferably used for fiber oils and the like. When the polyether of the present invention is used as a hydrous hydraulic oil, it is preferable to use it in combination with a carboxylic acid and an alkali metal compound or amine. The preferred content of the polyether of the present invention is 2 to 60% by weight, more preferably 5 to 40% by weight based on the total amount of the composition. If the amount is too small, the lubricating properties of the hydraulic oil will be insufficient. As the carboxylic acid, those described above can be exemplified, but from the viewpoint of lubricity, odor and corrosion resistance, a monocarboxylic acid or dicarboxylic acid having 8 or more carbon atoms is preferable, and a monocarboxylic acid or dicarboxylic acid having 8 to 36 carbon atoms is preferable. More preferred. The content of the carboxylic acid is not particularly limited, but if it is too small, the rust resistance is not sufficient, and if it is too large, the viscosity of the hydraulic oil becomes too high. % By weight, more preferably 0.5 to 15% by weight. The alkali metal compound or amine is preferably contained in an amount equal to or more than the neutralization equivalent of the carboxylic acid. As the alkali metal compound, for example,
Examples include sodium hydroxide and potassium hydroxide. Examples of the amine include those described above.

In the hydrous hydraulic oil of the present invention, the above components are preferably used as an aqueous solution or an emulsion. Also, low molecular weight glycols such as ethylene glycol, diethylene glycol, propylene glycol, and dipropylene glycol, mineral oils, fats and oils, fatty acid esters, extreme pressure agents such as sulfur or phosphorus, surfactants, rust inhibitors, preservatives, and boric acid Etc. can be arbitrarily added.

When the polyether of the present invention is used as a metalworking oil, it is preferable to use it together with a carboxylic acid and an alkali metal compound or amine. The preferred content of the polyether of the present invention is 0.1 to 8 with respect to the total amount of the composition.
0% by weight, more preferably 3 to 50% by weight. If the amount is too small, the lubricating properties and defoaming properties of the metalworking oil become insufficient, and if it is too large, the viscosity of the metalworking oil becomes too high to withstand use. Examples of the carboxylic acid include those described above, but from the viewpoint of lubricity, odor and corrosion resistance, a monocarboxylic acid or dicarboxylic acid having 8 or more carbon atoms is preferable, and a monocarboxylic acid or dicarboxylic acid having 8 to 36 carbon atoms is preferable. More preferred. The content of the carboxylic acid is not particularly limited, but if it is too small, the rust resistance is not sufficient, and if it is too large, the viscosity of the hydraulic oil becomes too high. % By weight, more preferably 1 to
15% by weight is good. The alkali metal compound or amine is
The carboxylic acid is preferably contained in an amount equal to or greater than the neutralization equivalent. Examples of the alkali metal compound include sodium hydroxide and potassium hydroxide. Examples of the amine include those described above.

In the metalworking oil of the present invention, the above components are preferably used as an aqueous solution or emulsion. Also, low molecular weight glycols such as ethylene glycol, diethylene glycol, propylene glycol, and dipropylene glycol, mineral oils, fats and oils, fatty acid esters, extreme pressure agents such as sulfur or phosphorus, surfactants, rust inhibitors, preservatives, and boric acid , A dispersant, a water-soluble resin and the like can be arbitrarily added, and can be used as cutting oil, grinding oil, rolling oil, press oil, drawing oil, DI can production oil and the like.

When the polyether of the present invention is used as a fibrous oil agent, the polyether of the present invention can be used alone. However, if necessary, other polyethers, mineral oils, fatty acid esters and phosphate esters can be used. , Sulfate,
Silicone or the like may be used in combination. When applying to fibers, it is preferable to use it after diluting it to an appropriate concentration with water.

[0025]

The present invention will be described more specifically with reference to the following examples. In the following examples, parts and percentages are by weight unless otherwise specified. In the following Examples and Comparative Examples, EO is an ethylene oxide or oxyethylene group,
PO is a propylene oxide or oxypropylene group,
AO is an abbreviation for oxyalkylene group.

Example 1 A propylene glycol 56 was placed in a 3 liter internal pressure vessel equipped with a stirrer and a thermometer.
g (1 mol) and 5.6 g (0.1 mol) of potassium hydroxide were charged, the atmosphere in the vessel was replaced with nitrogen, and the temperature was raised to 100 ° C. to dissolve potassium hydroxide. Under a nitrogen atmosphere, PO was charged with 1,972 g (34 mol) of PO and a reaction temperature of 10%.
The reaction was performed at 0 to 150 ° C. Of the reactants, 1,0
17 g (0.5 mol) was transferred to a pressure vessel having an inner volume of 20 liters, and mixed alkylene oxides were reacted under the same conditions in the reaction order shown in Table 1 below to obtain the following polyether 1.

[0027]

[Table 1]

[0028]

Embedded image

Here, (AO) is a polyoxyalkylene chain having the following structure, and the PO content in (AO) is 35%
It is.

[0030]

Embedded image

(PO / EO) _18/10 is a group of random polymerization of PO and EO, which means that the average number of moles of PO added is 18 and the average number of moles of EO added is 10. The same description applies to other parts and the following examples and comparative examples.

Example 2 92 g (1 mol) of glycerin instead of 56 g of propylene glycol, 1,914 g of PO
(33 mol) and 11.2 g (0.2 mol) of potassium hydroxide in the first stage reaction under the same conditions as in Example 1, and 669 g (0.33 mol) of this reaction product was used. ,
Subsequent addition of the alkylene oxide was performed according to the reaction order and the number of moles of the reaction shown in Table 2 to obtain the following polyether 2.

[0033]

[Table 2]

[0034]

Embedded image

Here, (AO) is a polyoxyalkylene chain having the following structure, and the PO content in (AO) is 35%
It is.

[0036]

Embedded image

Example 3 134 g (1 mol) of trimethylolpropane instead of 56 g of propylene glycol, P
348 g (6 mol) of O and 5.6 g of potassium hydroxide
(0.1 mol), and the first-stage reaction was carried out under the same conditions as in Example 1, and 161 g (0.33 mol) of this reaction product was used.
Table 3 shows the subsequent addition of the alkylene oxide.
The following polyether 3 was obtained according to the reaction sequence and the number of moles of reaction shown in

[0038]

[Table 3]

[0039]

Embedded image

Here, (AO) is a polyoxyalkylene chain having the following structure, and the PO content in (AO) is 48%
It is.

[0041]

Embedded image

Example 4: Instead of 56 g of propylene glycol, 48 g (1.5 mol) of methanol and 330 g of EO
(7.5 mol), 1,740 g (30 mol) of PO and 11.2 g (0.2 mol) of potassium hydroxide were used to carry out the first-stage reaction under the same conditions as in Example 1. Using 1,412 g (1 mol), the subsequent addition of alkylene oxide was carried out according to the reaction sequence and the number of moles shown in Table 4, to obtain the following polyether 4.

[0043]

[Table 4]

[0044]

Embedded image

Here, (AO) is a polyoxyalkylene chain having the following structure, and the PO content in (AO) is 65%
It is.

[0046]

Embedded image

Example 5 130 kg (100 mol) of 2-ethylhexanol and 560 potassium hydroxide were placed in a pressure vessel having an internal volume of 300 liters equipped with a stirrer and a thermometer.
g (10 mol), and the inside of the vessel is replaced with nitrogen.
The temperature was raised to 0 ° C. to dissolve potassium hydroxide. Thereafter, under nitrogen atmosphere, 145 kg (2,500 mol) of PO and E
66 kg (1,500 mol) of O.
The reaction was carried out at 50 ° C. to obtain the following polyether 5. still,
This pressure vessel was equipped with an alkylene oxide mixing device outside, and the reaction was performed by continuously changing the mixing ratio of ethylene oxide and propylene oxide as shown in FIG.

[0048]

Embedded image

Here, (AO) is a polyoxyalkylene chain having the following structure, and the PO content in (AO) is 69%
It is.

[0050]

Embedded image

Comparative Example: As a comparative product, PO in (AO)
The following polyethers 6 to 9, which are random or block polymers having no change in the ratio of the number of moles of EO added to EO, were prepared under substantially the same conditions as in Example 1.

[0052]

Embedded image

[0053]

Embedded image

[0054]

Embedded image

[0055]

Embedded image

Next, in order to evaluate the performance of the polyether of the present invention as a lubricant, various evaluation tests were carried out using these polyethers as follows.

(1) Lubricity Test A 30% aqueous solution of the polyether of the present invention and the comparative product was tested for lubricity in a shell type high-speed four-ball tester manufactured by Shinko Zoki Co., Ltd. under the following conditions. Was measured. The results are shown in Table 5. <Conditions> Load: 490 N Rotation speed 1,500 rpm Test time: 60 seconds

[0058]

[Table 5]

(2) Test as Hydraulic Hydraulic Oil A hydrous hydraulic oil composition having the composition shown in Table 6 was prepared and tested as a hydrous hydraulic oil using a Vickers V-104-E type vane pump. . That is, these hydraulic oils are supplied under pressure by a pump under the following conditions, the kinematic viscosity at 40 ° C., the cam bearing wear amount (mg) after 50 hours and 100 hours, the vane wear amount (mg), and the vane tip portion Was measured for sludge adhesion. Table 6 shows the results. <Conditions> Oil amount: 40 liters Relief valve set pressure: 690 N Rotational speed: 1,200 rpm Pump inlet temperature: 50 ° C

[0060]

[Table 6]

The determination of the state of sludge adhesion is as follows. ：: no to little deposits Δ: slight deposits ×: lots of deposits

(3) Test as an Aqueous Metalworking Oil An aqueous metalworking oil composition having the composition shown in Table 7 was prepared, and its lubricity was evaluated using a Falex tester. That is, the test was conducted under the following conditions, and the wear amount (m
g) was measured. Table 7 shows the results. <Conditions> Sample concentration: 5% aqueous solution Rotation speed: 290 rpm Test time: 1 hour Pressure: 890 N

[0063]

[Table 7]

(4) Test as fiber oil agent 250 denier polyester filament and 70 denier nylon filament were washed with hot water and dried to obtain test fibers. Roller oiling a 10% aqueous solution of the fiber oil shown in the table, adjust the adhesion amount of the fiber oil to 1% after drying, and measure the fiber-metal friction coefficient with a fiber-metal running friction coefficient measuring machine. Was measured. The material of the metal is matte chrome plating, and the running speed of the filament is 200 m /
Minutes. Table 8 shows the results.

[0065]

[Table 8]

[0066]

The effect of the present invention is to provide a polyether having a specific polyoxyalkylene chain and excellent lubricity, and a method for producing the same.

[Brief description of the drawings]

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a graph in which the horizontal axis represents the number of moles of alkylene oxide added per active hydrogen and the vertical axis represents the mole% of ethylene oxide in the mixed alkylene oxide chain of the polyether. The change of the mixing ratio of alkylene oxide accompanying addition of alkylene oxide is shown.

Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat II (reference) // C10N 30:06 40:20 (72) Inventor Yoshio Minowa 7-35 Higashiogu, Arakawa-ku, Tokyo Asahi Denka F-term (reference) in Kogyo Co., Ltd.

Claims (8)

[Claims] 1. A structure having two or more different groups in which two or more alkylene oxides are randomly added to an active hydrogen-containing compound, and the mixing ratio of the alkylene oxides between these groups is different from each other. Or a single mixed polyoxyalkylene chain having a structure in which two or more alkylene oxides are randomly added and the mixing ratio of these alkylene oxides changes continuously. A polyether comprising: 2. A polyether compound having a mixed polyoxyalkylene chain obtained by randomly adding a mixed alkylene oxide obtained by mixing two or more alkylene oxides to an active hydrogen-containing compound, wherein the mixed polyoxyalkylene is Part or all of the chain is a polyoxyalkylene chain formed by an addition method in which the mixing ratio in the mixed alkylene oxide changes stepwise or continuously as the mixed alkylene oxide addition reaction proceeds. Polyether. 3. The polyether according to claim 1, wherein one of the two or more alkylene oxides is ethylene oxide. 4. An active hydrogen-containing compound is first added with propylene oxide alone, then with a mixed alkylene oxide of ethylene oxide and propylene oxide, and then gradually with ethylene oxide and propylene oxide as the addition reaction proceeds. The polyether according to claim 1 or 2, obtained by changing the mixing ratio of propylene oxide in a stepwise or continuous manner so that the mixing ratio of propylene oxide in the mixed alkylene oxide is reduced. 5. A method for producing a polyether compound having a mixed polyoxyalkylene chain, wherein a mixed alkylene oxide obtained by mixing two or more alkylene oxides is added to an active hydrogen-containing compound at random. A polyether, wherein the method for adding part or all of the polyoxyalkylene chain is an addition method in which the mixing ratio in the mixed alkylene oxide changes stepwise or continuously as the addition reaction of the mixed alkylene oxide proceeds. Manufacturing method. 6. A lubricant comprising the polyether according to claim 1 or 2. 7. An aqueous lubricant comprising the polyether according to claim 1 or 2. 8. An aqueous hydraulic oil, an aqueous metalworking oil or a fiber oil agent comprising the polyether according to claim 1 or 2.