JPH11228686A - Polyether derivative and its production - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a polyether derivative capable of exhibiting excellent variety of use, affinity for resins and function maintenance of agent used together with the derivative, useful as an antistatic agent, etc., by including a specific nonionic hydrophilic group and an aromatic ring-containing hydrophobic group in the molecule. SOLUTION: This compound is shown by the formula [R<1> is a (substituted) 6-30C monohydric phenol residue or a (substituted) 6-30C aromatic ring- containing monohydric residue; A is a 2-4C alkylene; Y is an (aromatic ring- containing) 1-15C dihalide residue; 1<=n<=100] and is obtained, for example, by subjecting an alkylene oxide addition polymerization to a monohydric phenol or an aromatic ring containing alcohol to give a polyether monool and reacting the monool with a dihalide.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a novel polyether derivative. More specifically, the present invention relates to a polyether derivative having excellent heat resistance and having no reactive group in the molecule.

[0002]

2. Description of the Related Art Polyether derivatives are synthesized by subjecting compounds having active hydrogen to addition polymerization of alkylene oxides such as ethylene oxide and propylene oxide, and adding various modifications as necessary. Those having various properties such as low viscosity to high viscosity, oil solubility to water solubility, and low melting point to high melting point can be obtained. Since derivatives having a wide range of properties can be obtained, the uses are widely used in the fields of medicine, cosmetics, fermentation industry, lubricating oils, resins, and silicone resins. The study of metamorphic technology is also active, and attempts are being made to expand applications. For example, among the polyether derivatives, oligomers having a relatively large molecular weight include resins and fibers such as antistatic agents, surface hydrophilic agents, water-absorbing agents, plasticizers, solid polymer electrolytes, surfactants, and lubricating oils. Although it has been put to practical use in various fields, improvement studies are still ongoing, and it is possible to respond to new market needs by developing new metamorphic methods.

[0003] First, the antistatic agent includes a surfactant type low molecular weight compound and a polymer type permanent antistatic agent. Representative polymer antistatic agents that are currently in practical use include polyethylene glycol methacrylate, as described in Kiyoshi Akamatsu, “Latest Technologies and Applications of Antistatic Materials,” CMC, p99 (1996). There are copolymers, polyetheresteramides, polyetheramideimides, polyethylene oxide-epichlorohydrin copolymers and the like, but they have problems in heat resistance, discoloration resistance, falling off during processing, and the like. In addition, when the thermoplastic resin is melt-kneaded, for example, with a polyester resin, if the compound has a functional group that causes a transesterification reaction, the resin is reduced in the degree of polymerization and the physical properties are reduced. Further, in the case of polycarbonate resin, for example, as disclosed in Japanese Patent Application Laid-Open No. 9-25335, an antistatic agent which does not impair the transparency of the inherent resin has been studied. Improvement is required due to low cost. As described above, not only the antistatic property but also various functions are required, and there is a demand for fine material handling and technical innovation according to the application.

On the other hand, in various fields such as inks, toners, paints, resins, rubbers, fibers, papers, photographs, films, etc., strength, rigidity, adhesiveness, heat resistance, weather resistance, color tone, deep color, matte, Silica, for the purpose of improving various properties such as whitening (hiding properties), tactile properties, slipperiness, abrasion resistance, and viscosity, adding cost as an extender, and adding new functions such as conductivity, Inorganic fine particles such as calcium carbonate, titanium dioxide, talc, ferrite, metal powder, metal fiber, and glass fiber, and organic pigments are used. However, the surface of the inorganic fine particles is generally poor in lipophilicity because it is covered with a polar group such as a hydroxyl group or adsorbed water, and as it is, it is difficult to uniformly disperse it in an organic medium such as a resin or rubber. However, the purpose cannot be sufficiently achieved, for example, by coagulation in a non-aqueous vehicle to lose color unevenness and gloss.

[0005] In order to improve the dispersibility by changing the surface properties of the inorganic fine particles and the pigment, a method of treating with various coupling agents or coating with various surfactants or resins has been used. For example, Japanese Patent Publication No. 7-98657 discloses a special silylating agent, and Japanese Patent Publication No.
Surface modifiers consisting of long-chain amides are each described. These conventional surface modifiers and dispersants have problems in dispersibility, heat resistance, economy, compatibility with matrix resin, etc., especially non-reactivity with matrix resin,
Few satisfy the requirements such as not hindering the performance of other additives and modifiers, and preventing fine particles from adsorbing and deactivating other additives and modifiers. It is generally said that polyether derivatives are susceptible to deterioration due to heat or oxidation, and resins,
Despite exhibiting excellent performance as a lubricating oil raw material, thermal decomposition properties and thermal deterioration properties are problematic, and many improvements have been studied. By introducing an aromatic ring into the molecule or by using a stabilizer such as an antioxidant in combination, heat resistance can be improved, and as a method of introducing an aromatic ring, an aromatic ring such as a polyhydric phenol or an aromatic amine is used. Produced by adding an alkylene oxide to an active hydrogen compound having
7-151613) and those prepared by adding an aromatic ring-containing alkylene oxide such as styrene oxide to an active hydrogen-containing compound (L. Shechter et al., Ind. Eng. Che.
m., 48, 1107 (1957), etc.), but these heat-resistant polyether derivatives are limited in the content of aromatic ring that can be introduced, and have a structure in which the aromatic ring is not in the main chain. There are problems that the effect of improving the properties is small and that the resin has a reactive group so that the physical properties of the resin are reduced and the performance of other additives is hindered.

A desirable molecular structure of the polyether derivative for the above-mentioned uses and problems consists of a hydrophilic group and a hydrophobic group, the amount of which can be controlled by the use and required functions. From the viewpoint of applicability, a nonionic polyalkylene oxide chain is appropriate, and it is necessary that the molecular weight can be controlled between several hundreds and several tens of thousands in accordance with compatibility with the resin and required functions. The hydrophobic group preferably has an aromatic ring in consideration of heat resistance and affinity with an aromatic resin which is a matrix resin assumed for use as a resin modifier. Furthermore, it is important that the resin does not have a reactive group because the physical properties of the resin are not lowered by melt-kneading with a polyester resin or the like, and the functions of various concomitant drugs are not hindered. Polyether derivatives satisfying these items are not known.

[0007]

SUMMARY OF THE INVENTION Accordingly, an object of the present invention is to provide both a hydrophilic group comprising a nonionic polyalkylene oxide and a hydrophobic group having an aromatic ring, and to have a reactive group in the molecule. Another object of the present invention is to provide a polyether derivative in which the amounts and the molecular weights of the hydrophilic group and the hydrophobic group are controlled without any problem.

[0008]

Means for Solving the Problems As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that polyether derivatives having a structure represented by the following general formula (1) have various properties. To complete the present invention. That is, the present invention provides a novel polyether derivative represented by the following general formula (1).

[0009]

Embedded image R ¹ O- (AO) nY- (OA) n-OR ¹ (1)

(Wherein, R ¹ represents a residue of a monohydric phenol having 6 to 30 carbon atoms which may have a substituent or a residue of a monohydric alcohol having an aromatic ring; Represents an alkylene group of 2 to 4, Y represents a residue of a dihalide having 1 to 15 carbon atoms having or not having an aromatic ring, and 1 ≦ n ≦
The present invention also provides a method for producing a polyether oligomer, which comprises reacting a polyether monool obtained by addition-polymerizing an alkylene oxide with a monohydric phenol or a monohydric alcohol having an aromatic ring and a dihalide. It provides a method.

[0011]

BEST MODE FOR CARRYING OUT THE INVENTION The polyether derivative of the present invention comprises
A polyether oligomer represented by the above general formula (1) obtained by reacting a dihalide with a polyether monool obtained by addition-polymerizing an alkylene oxide to a monohydric phenol or a monohydric alcohol having an aromatic ring, and having a nonionic property. And a block type polyether derivative having both a hydrophilic group comprising a polyalkylene oxide and a hydrophobic group having an aromatic ring, and controlling the amount and molecular weight thereof. The present invention also provides a method for producing a polyether oligomer, comprising reacting a diether halide with a polyether monool obtained by addition-polymerizing an alkylene oxide to a monohydric phenol or a monohydric alcohol having an aromatic ring. In the most preferred example of the compound of formula (I).

As the residue R ¹ of a monohydric phenol or a monohydric alcohol having an aromatic ring, for example, benzyl alcohol, phenol, cresol, xylenol, ethylphenol, propylphenol, butylphenol, hexylphenol, octylphenol, nonylphenol And phenols having an aromatic substituent such as phenylphenol, styrenated phenol, cumylphenol and the like. Of these, preferred are residues of benzyl alcohol, phenol, cresol, ethylphenol, propylphenol, butylphenol, cumylphenol and styrenated phenol, and particularly preferred are residues of cumylphenol and styrenated phenol. .

The alkylene group A is an alkylene group having 2 to 4 carbon atoms, and particularly preferably contains an ethylene group in order to impart a hydrophilic group. Propylene groups and butylene groups can also be appropriately incorporated for the purpose of imparting hydrophobicity, changing fluidity or crystallinity, but need not necessarily be included. The residue Y of the dihalide is not particularly limited,
Residues of methylene dihalide such as methylene chloride (methylene group), residues of ethylene dihalide (ethylene group), residues of propylene dihalide (propylene group), residues of bis (halomethyl) benzene (xylylene group), etc. Can be mentioned. In the polyether derivative of the present invention, the type and content of the aromatic ring in the compound can be controlled by selecting the type of the dihalide.

Here, the average value n of the number of moles of the alkylene oxide added in the general formula (1) is 1 ≦ n ≦ 100, but the optimum value depends on the application. When n is larger than 100, performance as an additive or a modifier cannot be obtained, and the viscosity becomes high, so that the synthesis becomes difficult. With respect to the type of alkylene oxide, ethylene oxide is particularly preferred as the hydrophilic group. Propylene oxide, butylene oxide, and the like can be appropriately incorporated for the purpose of imparting hydrophobicity, changing fluidity or crystallinity, but need not necessarily be included. A in the general formula (1) is determined according to the type of the alkylene oxide used here. Further, depending on the charged amount of the alkylene oxide with respect to the phenol, n
Can control

When the alkylene oxide is added, the reaction is carried out in the presence of a catalyst such as an acid catalyst or an alkali catalyst, preferably under pressure, at an elevated temperature (for example, 80 to 200 ° C., preferably 1 to 200 ° C.).
(00-180 ° C.) by known methods. The catalyst can be an acid catalyst, for example a Lewis acid such as boron trifluoride or aluminum chloride, but more preferably an alkali catalyst, for example an alkali metal or alkaline earth metal alcoholate, hydroxide, oxide. , Carbonates, hydrides or amides. Particularly preferred catalysts are sodium or potassium alcoholates (eg methylates or ethylates) and hydroxides. The catalyst is usually used in an amount of from 0.05 to
It is used in an amount of 3% by weight, preferably 0.1-1% by weight. After completion of the reaction, the catalyst is removed by neutralization, filtration, treatment with an adsorbent or the like as necessary.

The polyether derivative of the present invention basically does not have a highly reactive functional group such as a hydroxyl group, an amino group, an ester bond or a urethane bond. Therefore, there is no decrease in the physical properties of the resin, no inhibition of the function of the concomitant drug, and no coloring. Also, heat resistance is good as a polyalkylene oxide derivative. As a method for producing the polyether derivative of the present invention from the obtained polyether monol, a polyhydric phenol or a polyhydric alcohol having an aromatic ring and an alkylene oxide addition-polymerized polyether monol are linked with a dihalide. Can be preferably used. In this method, when a dihalide containing no aromatic ring is used, a polyether derivative having an aromatic ring only at both ends can be synthesized. When a dihalide having an aromatic ring is used, a polyether derivative having an aromatic ring at both ends and at three places inside can be synthesized.

The reaction for forming an ether bond by reacting a dihalide with a polyether monool is carried out by treating a terminal hydroxyl group of a polyether with an alkali metal compound and then reacting with a dihalide. In addition, it can also synthesize | combine using a quaternary ammonium salt, such as a tetrabutyl ammonium halide, instead of an alkali metal compound, or using together with an alkali metal compound. By-produced salt and the like are dissolved or dispersed by adding water, and separated from the polyalkylene oxide derivative by two layers. A small amount of residual salt or the like is filtered by filtration or treatment with an adsorbent.
A method of diluting the product with a solvent such as toluene and filtering off salt and the like is also possible.

Examples of the alkali metal compound include caustic alkalis such as sodium hydroxide and potassium hydroxide, metal alcoholates of lower alcohols such as sodium methylate, sodium ethylate and potassium t-butoxy, and alkali metal such as metal sodium and potassium metal. And the like,
Usually, some or all of the hydroxyl groups of the polyether are converted to alcoholates and subjected to a reaction with a halide. Among these, preferred are metal alcoholates and caustic alkalis, and more preferred are sodium methylate, sodium hydroxide and potassium hydroxide.

Examples of monohydric phenols or monohydric alcohols having an aromatic ring include benzyl alcohol,
Examples include alkylphenols such as phenol, cresol, xylenol, ethylphenol, propylphenol, butylphenol, hexylphenol, octylphenol, and nonylphenol, and phenols having an aromatic substituent such as phenylphenol, styrenated phenol, and cumylphenol. Among these, preferred are residues of benzyl alcohol, phenol, cresol, ethylphenol, propylphenol, butylphenol, cumylphenol and styrenated phenol, and particularly preferred are cumylphenol and styrenated phenol. Examples of the dihalide include methylene dihalides such as methylene chloride and methylene bromide, alkylene dihalides such as ethylene dihalide, halogenated aromatic ring-containing hydrocarbons such as benzal chloride and bis (chloromethyl) benzene, and bis (chloro). Examples include halogenated ethers such as methyl) ether and halogenated ketones such as bis (chloromethyl) ketone. Of these, methylene chloride and bis (chloromethyl) benzene are particularly preferred.

In the present invention, a solvent can be used if necessary. As the solvent, those which do not have active hydrogen such as ethers, aliphatic hydrocarbons, aromatic hydrocarbons and ketones are suitable, but when the polyether is alcoholated and then reacted with a halide. For example, tertiary alcohols such as t-butanol can be used. In general, polyether derivatives are alkaline and heated, and in particular color when in contact with air. This is thought to be due to the presence of oxidation products such as aldehydes in the polyether derivative, which can be improved by performing a reduction treatment in advance by sodium borohydride treatment or the like and avoiding contact with air during the reaction. Incidentally, the balance between the hydrophobic group and the hydrophilic group and the magnitude of the surface energy are determined by R in the general formula (1).
The number of ¹ aromatic ring, the kind of Y, can be controlled by the alkylene oxide type and number of added moles n.

The polyether derivative of the present invention can be used for a wide variety of applications because of its wide range of structural designs. The optimum structure depends on the application. Applications include micro-phase-separated structures, amphiphilicity, surface activity, etc., which require compounding of physical properties and functions, such as antistatic agents such as resins, surface hydrophilic agents, etc.
It is used as a plasticizer, a melt viscosity lowering agent, a compatibilizer, an adhesive, an inorganic fine particle dispersant, a surface treatment agent, a solid polymer electrolyte, and the like. In addition, lubricating base oils having excellent heat resistance and oxidation stability can be used.

[0022]

EXAMPLES Hereinafter, the present invention will be further described with reference to Examples, but it should be understood that the present invention is not limited to the following Examples unless it exceeds the gist thereof. The “parts” in the examples are by weight. In the examples, the number of moles of the alkylene oxide added to the phenol was determined from the hydroxyl value. The final product was analyzed by ¹ H-NMR (JNM-LA400 type FT-NMR apparatus manufactured by JEOL Ltd.).

Example 1 Ethylene oxide 27 was added to 100 parts of p-cumylphenol.
8 parts in the presence of 0.4 parts of potassium hydroxide, 120-1
The reaction was carried out at 40 ° C. to give an adduct of p-cumylphenol with an average of 13 mol of ethylene oxide (hereinafter referred to as p-cumylphenol / 13EO adduct) (hydroxyl value 72 mg KOH
/ G) was synthesized. This p-cumylphenol 13E
27 parts of 28% sodium methylate was charged to 100 parts of the O adduct, and methanol was removed at 85 to 120 ° C. under reduced pressure. After returning to atmospheric pressure with nitrogen and cooling to 40 ° C., 11 parts of methylene chloride was gradually added dropwise. Then, raise the temperature to 70-1
The reaction was performed at 00 ° C. for 3 hours. Then, add water and add p with phosphoric acid.
After neutralization to H6, the mixture was allowed to stand, and the lower aqueous layer and salt were removed.
After removing the volatile components under reduced pressure, the adsorbent Kyoward 60
1S (manufactured by Kyowa Chemical Industry Co., Ltd.) and treatment at 100 ° C., the adsorbent is removed by filtration, and the polyether derivative (P
CP / 13EO / DCM). Structure of obtained polyether derivative and assignment of ¹ H-NMR signal
(δ value) is shown below.

[0024]

Embedded image

Example 2 α, α'-dichloroxylene 1 in place of methylene chloride
A polyether derivative (abbreviated as PCP / 13EO / DCX) was obtained according to Example 1, except that 4 parts were used. Structure and ¹ H-NMR of the obtained polyether derivative
The assignment (δ value) of the signal is shown below.

[0026]

Embedded image

Example 3 Ethylene oxide 1 was added to 100 parts of distyrenated phenol.
80 parts in the presence of 0.2 parts sodium hydroxide, 120 parts
Reaction at ~ 150 ° C to give distyrenated phenol-1
A 2EO adduct (hydroxyl value 68 mgKOH / g) was synthesized. 26 parts of 28% sodium methylate was charged to 100 parts of a distyrenated phenol / 12EO adduct, and methanol was removed at 85 to 120 ° C. under reduced pressure. After returning to atmospheric pressure with nitrogen and cooling to 40 ° C., 10 parts of methylene chloride was gradually added dropwise. Thereafter, the temperature was raised and the reaction was carried out at 70 to 100 ° C. for 3 hours. Next, salt removal and adsorbent treatment were performed in the same manner as in Example 1 to obtain a polyether derivative (SP / 12EO / D).
CM). The structure of the obtained polyether derivative and the assignment (δ value) of ¹ H-NMR signal are shown below.

[0028]

Embedded image

Example 4 To 100 parts of nonylphenol was added 245 parts of ethylene oxide, and 120 to 140 parts in the presence of 0.1 part of potassium hydroxide.
The reaction was carried out at a temperature of ° C to synthesize a nonylphenol / 12EO adduct (hydroxyl value: 75 mgKOH / g). 28 parts of 28% sodium methylate was charged to 100 parts of the nonylphenol / 12EO adduct, and methanol was removed at 85 to 120 ° C. under reduced pressure. After returning to atmospheric pressure with nitrogen and cooling to 40 ° C., 11 parts of methylene chloride was gradually added dropwise. Thereafter, the temperature was raised and the reaction was carried out at 70 to 100 ° C. for 3 hours. Then
Salt removal and adsorbent treatment were performed in the same manner as in Example 1 to obtain a polyether derivative (abbreviated as NP / 12EO / DCM). Structure and ¹ H-NMR of the obtained polyether derivative
The assignment (δ value) of the signal is shown below.

[0030]

Embedded image

Example 5 100 parts of phenol was reacted with 669 parts of ethylene oxide in the presence of 0.8 part of sodium hydroxide at 120 to 150 ° C. to synthesize a phenol / 14EO adduct (hydroxyl value: 77 mgKOH / g). Was synthesized. 30 parts of 28% sodium methylate was charged to 100 parts of the phenol / 14EO adduct, and methanol was removed under reduced pressure at 85 to 120 ° C. After returning to atmospheric pressure with nitrogen and cooling to 40 ° C., 12 parts of methylene chloride was gradually added dropwise. afterwards,
The temperature was raised and the reaction was carried out at 70 to 100 ° C. for 3 hours. Next, salt removal and adsorbent treatment were performed in the same manner as in Example 1 to obtain a polyether derivative (abbreviated as PH / 14EO / DCM).
The structure of the obtained polyether derivative and the assignment (δ value) of ¹ H-NMR signal are shown below.

[0032]

Embedded image

Example 6 100 parts of cresol was reacted with 590 parts of ethylene oxide at 120 to 150 ° C. in the presence of 0.7 part of sodium hydroxide to synthesize a cresol-14EO adduct (hydroxyl value 79 mg KOH / g). Was synthesized. 29 parts of 28% sodium methylate was charged to 100 parts of the phenol / 14EO adduct, and methanol was removed at 85 to 120 ° C. under reduced pressure. After returning to atmospheric pressure with nitrogen and cooling to 40 ° C., 11 parts of methylene chloride was gradually added dropwise. Thereafter, the temperature was raised and the reaction was carried out at 70 to 100 ° C. for 3 hours. Next, salt removal and adsorbent treatment were performed in the same manner as in Example 1 to obtain a polyether derivative (abbreviated as CR / 14EO / DCM). The structure of the obtained polyether derivative and the assignment (δ value) of ¹ H-NMR signal are shown below.

[0034]

Embedded image

Comparative Example 1 p-cumylphenol.13EO synthesized in Example 1
The adduct (abbreviated PCP / 13EO) was used.

Comparative Example 2 28% to 100 parts of p-cumylphenol / 13EO adduct (hydroxyl value: 72 mg KOH / g) synthesized in Comparative Example 1
Charge 27 parts of sodium methylate,
At 20 ° C., the methanol was removed. After returning to atmospheric pressure with nitrogen and cooling to 40 ° C., 8.0 parts of methyl chloride was gradually injected. Thereafter, the temperature was raised and the reaction was carried out at 70 to 90 ° C. for 3 hours. Next, salt removal and adsorbent treatment were performed in the same manner as in Example 1 to obtain a polyether derivative (PCP / 13EO / Me).
Abbreviation).

REFERENCE EXAMPLE Regarding the polyether derivative of the present invention in each of the above examples and the polyether derivative of each comparative example, the thermal decomposition onset temperature and the specific properties of the polyester resin after melt-kneading each polyether derivative into the polyester resin. The viscosity was measured. The measurement results are shown in Table 1 below. In addition, the measuring method and conditions are as follows. [Measurement of Thermal Decomposition Temperature] Using a thermogravimetric analysis (TGA) measuring device, the temperature was raised from room temperature to 600 ° C. at a rate of 10 ° C./min in a stream of nitrogen or air, and the inflection point temperature at which weight loss started was determined. I asked.

[Production of Polyester Resin Containing Polyether Derivative] Five parts of various polyether derivatives were mixed and mixed with 100 parts of a polyester resin dried at 150 ° C. for 15 hours. The obtained mixture was used in a laboratory plast mill (manufactured by Toyo Seiki Seisaku-sho, Ltd., under the following conditions: test rotation speed: 15 rpm, test temperature T ₁ : 250 ° C., T ₂ : 260 ° C., T ₃ : 270).
C., T ₄ : 280 ° C.) to obtain pellets.

[Intrinsic Viscosity] The intrinsic viscosity of a polyester resin blended with various polyether derivatives was measured at 30 ° C. with phenol / ethane tetrachloride (weight ratio 1: 1) using a viscosity tube. The intrinsic viscosity of the polyester resin not containing the polyether derivative measured in the same manner was 0.62 cm ³ / g.
Met.

[0040]

[Table 1]

As described above, the polyether derivative of the present invention has excellent thermal stability and does not lower the intrinsic viscosity of the resin when blended with the resin.

[0042]

According to the present invention, a novel polyether derivative comprising an aromatic ring and a polyalkylene oxide chain is provided. The balance and molecular weight of the hydrophobic group and the hydrophilic group of the polyether derivative of the present invention can be arbitrarily controlled, so that it is possible to obtain a polyether derivative having an arbitrary structure suitable for use and required physical properties. Furthermore, since it has good heat resistance and no reactive groups, it has the characteristic that the performance of the matrix resin is not degraded and the performance of other additives and modifiers is not hindered.

Claims (4)

[Claims] 1. A polyether derivative represented by the following general formula (1): ## STR1 ## ^{R 1 O- (AO) n-} Y- (OA) n-OR 1 (1) ( In the formula, R ¹ Represents a residue of a monohydric phenol having 6 to 30 carbon atoms which may have a substituent or a residue of a monohydric alcohol having an aromatic ring, A represents an alkylene group having 2 to 4 carbon atoms, Y has 1 to 15 carbon atoms with or without an aromatic ring.
Represents a residue of a dihalide, and represents 1 ≦ n ≦ 100). 2. The polyether derivative according to claim 1, wherein Y is selected from the group consisting of a methylene group, an ethylene group, a propylene group, and a xylylene group. 3. The method according to claim 1, wherein R ¹ is selected from the group consisting of residues of benzyl alcohol, phenol, cresol, ethylphenol, propylphenol, butylphenol, cumylphenol, styrenated phenol, octylphenol and nonylphenol. Polyether derivatives. 4. A method for producing a polyether derivative represented by the general formula (1), wherein a polyether monool obtained by addition-polymerizing an alkylene oxide to a monohydric phenol or a monohydric alcohol having an aromatic ring is reacted with a dihalide. .