JP4843777B2 - Compound in which two molecules of crown ether derivative consisting of crown ether derivative and secondary ammonium salt are combined and method for producing the same - Google Patents

Description

[0001]
[Technical field to which the invention belongs]
The present invention relates to a compound obtained by binding two crown ether derivatives consisting of a crown ether derivative and a secondary ammonium salt, and a method for producing the same.
[0002]
[Prior art]
The main chain structure of the polymer compound varies depending on the type of monomer and the polymerization mode.
Various high molecular weight compounds such as polymer compounds containing carbon single bonds, double bonds, triple bonds, polymer compounds containing ester, ether, amide bonds, and polymer compounds containing metals in the main chain. Molecular compounds are known.
A polymer compound obtained by polymerizing such a monomer is a structure obtained by a main chain structure bonded by covalent bonding of monomer molecules. These conventional synthetic polymers have emerged as alternatives to traditional materials such as metal, wood, glass, and natural fibers, resulting in characteristics such as lighter weight, higher energy efficiency, higher performance, and higher durability. It has revolutionized society by adding to materials.
However, nowadays, there is a need for materialization technology and materials with higher environmental performance and reduced environmental burden. To meet this demand, recently, instead of covalently linking monomer molecules, we are trying to synthesize non-covalent polymer compounds that are linked by relatively weak interactions such as hydrogen bonds and coordination bonds. Research is underway.
In the production of this non-covalently bonded polymer compound, it is important to newly create a compound corresponding to a conventional monomer unit, and it is necessary to select this compound.
[0003]
[Problems to be solved by the invention]
The subject of this invention is providing the compound containing the substituent which can be used for manufacturing noncovalent-type polymer | macromolecule and can form a novel noncovalent bond.
[0004]
[Means for Solving the Problems]
The present inventors can be used to produce non-covalent polymers.
The present inventors have intensively studied a compound containing a substituent capable of forming a new non-covalent bond, and newly produced a compound in which two molecules of a crown ether derivative composed of a crown ether derivative and a secondary ammonium salt are bonded. And it discovered that this compound could be made to associate by dissolving in a nonpolar solvent, and, as a result, a non-covalent bonding type polymer compound could be obtained.
As a result, it was found that a compound obtained by binding two molecules of a crown ether derivative obtained by reacting a compound comprising a crown ether derivative and a secondary ammonium salt is a constituent unit of a noncovalent polymer compound. Completed.
More specifically, it is as follows.
The compound containing the crown ether derivative and the secondary ammonium salt has the following general formula (II)
[Chemical 7]
(II)
(In the formula, G represents a reactive substituent, and P represents a protecting group for a secondary amine.)
A crown ether derivative compound containing dibenzo-24-crown-8-ether and a secondary amine. A compound in which two molecules of a crown ether derivative obtained by reacting this compound and linking two compounds and deprotecting them is combined is represented by the following general formula (I)
[Chemical 8]
(I)
(Wherein Q represents a substituent, and X represents an arbitrary anion atom or anion molecule), which is a compound in which two molecules of three kinds of crown ether derivatives are bonded.
The compound obtained by binding two molecules of the three types of crown ether derivatives represented by the general formula (I) thus obtained is dissolved in a non-polar solvent, so that the crown ether and the ammonium salt are separated. Spontaneous associations can occur through specific and strong interactions that work, and by self-assembly, new non-covalent assemblies can be produced.
[0005]
That is, according to the present invention, the following inventions are provided.
(1) A compound obtained by binding two molecules of a crown ether derivative, which is represented by the following general formula (I).
[Chemical 9]
(I)
(In the formula, Q represents a substituent, and X represents any anion atom or anion molecule.)
(2) After reacting a dibenzo-24-crown-8-ether represented by the following general formula (II) with a crown ether derivative compound composed of a secondary amine, the resulting compound is deprotected, By adding a compound containing an ionic atom or an anionic molecule, a compound represented by the general formula (I) is produced by binding two molecules of the crown ether derivative. The manufacturing method of the compound.
[Chemical Formula 10]
(II)
(In the formula, G represents a reactive substituent, and P represents a protecting group for a secondary amine.)
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(I)
(In the formula, Q represents a group obtained by reacting with the substituent G of the general formula (I), and X represents any anion atom or anion molecule.)
(3) After reacting a crown ether derivative compound composed of dibenzo-24-crown-8-ether represented by the following general formula (II) and a secondary amine together with a compound represented by the general formula ALA The resulting compound is deprotected, and a compound containing any anion atom or anion molecule is added to produce a compound in which two molecules of the crown ether derivative represented by the following general formula (I) are bound. A method for producing a compound in which two molecules of a crown ether derivative are bonded.
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(II)
(In the formula, G represents a reactive substituent, and P represents a protecting group for a secondary amine.)
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A-LA
(In the formula, A represents a group that reacts with the reactive substituent G of the general formula (II). L represents a group that does not react with the reactive substituent A, and is a group that links A and A together. .)
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(I)
(In the formula, Q represents a group obtained by reacting the substituent G of the general formula (I) with the substituent A of the compound A-LA, and X represents an arbitrary anion atom or anion molecule) To express.)
[0006]
DETAILED DESCRIPTION OF THE INVENTION
The compound of the present invention is a compound composed of three isomers having a chemical structure represented by the following general formula (I).
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(I)
In the formula, Q represents a group for bonding two compounds.
X represents an arbitrary anion atom or anion molecule. X represents any anion atom or anion molecule composed of a part of sodium perchlorate, ammonium hexafluorophosphate, trifluoroacetic acid and the like. This is for dissolving the monomer for producing a non-covalent polymer in a non-polar organic solvent.
[0007]
The mixture of three isomers represented by the general formula (I) is a crown ether composed of dibenzo-24-crown-8-ether represented by the following general formula (II) composed of the following two isomers and a secondary amine. Obtained by reacting derivatives.
A crown ether derivative obtained by linking dibenzo-24-crown-8-ether represented by the general formula (II) and a secondary amine is obtained by reacting an aldehyde-substituted crown ether with a benzylamine derivative. A compound was produced (Examples 1 and 2), and the imide was reduced to produce a secondary amino compound (a compound represented by the general formula (III). Example 3). The dibenzo thus obtained It is produced by protecting the NH group of a crown ether derivative consisting of -24-crown-8-ether and a secondary amine with a protecting group P (Example 4). The following groups are used as the protecting group.
Benzyloxycarbonyl group, tert-butyloxycarbonyl group, p-biphenylisopropyloxycarbonyl group, 3,5-dimethoxy-α, α-dimethylbenzyloxycarbonyl group, 9-fluorenylmethyloxycarbonyl group, methylsulfonylethyloxy Carbonyl group, isonicotyloxycarbonyl group, 2,2,2-trichloroethyloxycarbonyl group, 2- (trimethylsilyl) -ethoxycarbonyl group, formyl group, phthaloyl group, dithiasuccinoyl group, o-nitrophenylsulfenyl Group, 2-nitrophenylthio group, diphenylphosphinyl group and triphenylmethyl group.
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(III)
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(II)
[0008]
Furthermore, the reactive group G can be changed to other reactive groups as required (Examples 5 and 6).
When reacting two kinds of isomeric compounds represented by the general formula (II), the substituent G and G react to produce the compound of the general formula (I), and the substituent G is an arbitrary compound. In some cases, it is produced by bonding via A-LA.
In the general formula (I), Q is a structure in which substituents G having a structure represented by the following general formula (II) are reacted with each other, or any compound A-LA in which G and G are bonded to each other. Is a group formed as a result of reaction with A.
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(II)
[0009]
When G and G react directly, G is the same group (the same group reacts to form Q) and different groups (different groups react to form Q). There is.
In addition, when G and G react with A of any compound ALA that binds both, G and A react directly to form Q. In this case, G and G may be the same group or different groups. Similarly, A in ALA may be the same or different.
[0010]
When G and G react directly, G is the same group (the same group reacts to form Q), or different groups (different groups react to form Q). is there.
[0011]
(1) When using the same G group
G is an allyl group, and Q is an alkyl group.
[0012]
(2) About using different G groups
When the group of G is an amino group and an amide group, Q is an amide group,
When the group of G is an amino group and a thiolacetic acid group, Q is an amide group,
When the group of G is an amino group and a thiol acetate ester, Q is an amide group,
When G is an amino group or a trihaloketone, Q is an amide group,
When the group of G is an amino group and an aldehyde, Q is an imine,
When the group of G is an amino group and an alkene, Q is amino,
When the group of G is an amino group and an alkyne, Q is amino,
When the group of G is an amino group and an acyl halide, Q is an amide group,
When the group of G is an amino group and an ester, Q is an amide group,
When the group of G is an amino group and an isocyanate, Q is a urea bond,
When the G group is an amino group and an isothiocyanate, Q is a thiourea bond, and when the G group is an amino group and a sulfonyl halide, Q is a sulfonamide group, and the G group is an amino group or diazo group. In the case, Q is an amino group,
When G is an azide group or alkene, Q is aziridine,
When G group is an azide group and an alkyne, Q is triazole,
When G is a carboxylic acid and an alcohol, Q is an ester,
When G is carboxylic acid and alkene, Q is an ester,
When G is carboxylic acid and alkyne, Q is an ester,
When the group of G is a carboxylic acid and an ester, Q is an ester,
When G group is carboxylic acid and ether, Q is an ester,
When the group of G is a diazo group and an alcohol, Q is an ether,
When G is an ester and an alcohol, Q is an ester,
When G group is ether and alcohol, Q is ether,
When G is an alcohol and an alkyl halide, Q is an ether,
When G is an alcohol and an acyl halide, Q is an ester,
When G is nitrile and alcohol, Q is an ester,
When G group is thiol and alkyl halide, Q is thioether,
When G group is thiol and alkene, Q is thioether,
[0013]
(3) About the case where G and G are reacted with A of compound A-LA in order to bind both
In this case, G and A directly react to react two kinds of isomeric compounds represented by the general formula (II) to form the compound of the general formula (I) and form the substituent Q. . In this case, G and G may be the same group or different groups. Similarly, A in ALA may be the same or different.
L is a divalent alkyl group, oxyethylene group, polyvinyl ether, polysiloxane, From polyester It is a group that is selected and is not reactive. In some cases, L is not present and the reactive group A may be combined.
A is an amino group, an ester group (such as methyl ester, ethyl ester, or propyl ester), a carbonyl group, a vinyl group, an allyl group, a carboxy group (such as acetic acid or propionic acid as a carboxylic acid), or a thiol group (such as methanethiol or ethanethiol). Etc.), alkyl halides (brominated methylene, chlorinated methylene, etc.), alkylamine groups, hydroxyl groups, alkyl alcohol groups (methyl alcohol, ethyl alcohol, etc.), cyano groups, azo groups, isocyanate groups (isocyanates, isothiocyanates, etc.) It is.
A is selected as a group capable of reacting with G.
The combinations are as follows.
G is an amino group, A is an amide group (possible in reverse combination), Q is an amide group,
G is an amino group, A is a thiolacetic acid group (reverse combination is possible), Q is an amide group,
G is an amino group, A is a thiol acetate ester (reverse combination is possible), Q is an amide group,
G is an amino group, A is a trihaloketone (possible in reverse combination), Q is an amide group,
G is an amino group, A is an aldehyde (the reverse combination is possible), Q is an imine,
G is an amino group, A is an alkene (the reverse combination is possible), Q is amino,
G is an amino group, A is an alkyne (the reverse combination is possible), Q is amino,
G is an amino group, A is an acyl halide (the reverse combination is possible), Q is an amide group,
G is an amino group, A is an ester (the reverse combination is possible), Q is an amide group,
G is an amino group, A is an isocyanate (the reverse combination is possible), Q is a urea bond,
G is an amino group, A is an isothiocyanate (possible in reverse combination), Q is a thiourea bond,
G is an amino group, A is a sulfonyl halide (reversible combinations are possible), Q is a sulfonamide group,
G is an amino group, A is a diazo group (reversible combinations are possible), Q is an amino group,
G is an azide group, A is an alkene (possible in reverse combination), Q is aziridine,
G is an azide group, A is an alkyne (possible in reverse combination), Q is triazole,
G is a carboxylic acid, A is an alcohol (possible in reverse combination), Q is an ester,
G is a carboxylic acid, A is an alkene (possible in reverse combination), Q is an ester,
G is a carboxylic acid, A is an alkyne (possible in reverse combination), Q is an ester,
G is a carboxylic acid, A is an ester (the reverse combination is possible), Q is an ester,
G is a carboxylic acid, A is an ether (possible in reverse combination), Q is an ester,
G is a diazo group, A is an alcohol (possible in reverse combination), Q is an ether,
G is an ester, A is an alcohol (possible in reverse combination), Q is an ester,
G is ether, A is alcohol (possible in reverse), Q is ether,
G is alcohol, A is alkyl halide (possible in reverse combination), Q is ether, G is alcohol, A is acyl halide (reverse combination is possible), Q is ester,
G is a nitrile, A is an alcohol (possible in reverse), Q is an ester,
G is a thiol, A is an alkyl halide (reverse combination is possible), Q is a thioether, G is a thiol, A is an alkene (reverse combination is possible), Q is a thioether,
The R group is a group that does not react with the G group and the A group.
These groups need to be substituents having lower acidity than secondary ammonium.
[0014]
Q is a group formed by reacting the above ALA and G, or a group formed by reacting G with each other.
L is a divalent alkyl group, oxyethylene group, polyvinyl ether, polysiloxane, From polyester It is a group that is selected and is not reactive.
When A is an amino group, G is an amide, thiolacetic acid, thiolacetic acid ester, trihaloketone, aldehyde, alkene, alkyne, acyl halide, ester, isocyanate, isothiocyanate, sulfonyl halide, diazo group.
When A is an ester group, G is an amino group, a carboxylic acid, or an alcohol. When A is an ether group, G is a carboxylic acid or an alcohol.
When A is an alcohol, G is a carboxylic acid, a diazo group, an ester, an ether, an alkyl halide, an acyl halide, or a nitrile.
When A is an amide group, G is an amino group.
When A is thiol acetic acid, G is an amino group.
When A is a thiol acetate ester, G is an amino group.
When A is a trihaloketone, G is an amino group.
When A is an aldehyde, G is an amino group.
When A is an alkene, G is an amino group, an azide group, a carboxylic acid, or a thiol group.
When A is an alkyne, G is an amino group, an azide group, or a carboxylic acid.
When A is an acyl halide, G is an amino group or an alcohol.
When A is an isocyanate group, G is an amino group.
When A is an isothiocyanate group, G is an amino group.
When A is a sulfonyl halide, G is an amino group.
When A is an azo group, G is an amino group or an alcohol.
When A is an azide, G is an alkene or alkyne.
When A is a carboxylic acid, G is an alcohol, alkene, alkyne, ester or ether.
When A is an alkyl halide, G is an alcohol or a thiol.
When A is an acyl halide, G is an amino group or an alcohol.
When A is a nitrile, G is an alcohol.
When A is a thiol, G is an alkyl halide or alkene.
If an example of ALA is mentioned, as a specific compound, they are compounds, such as alkylene glycol, 1,4 diisocyanate butane, and 1,12 dibromo dodecane.
[0015]
As a result of protection by a protecting group, two crown ether derivatives consisting of dibenzo-24-crown-8-ether represented by the following general formula (II), which is an NP group, and a secondary amine are present. The substituent G of the crown ether derivative can be reacted with the substituent G of the other crown ether derivative by reacting with the substituent G of the other crown ether derivative or by the compound A-LA. A compound (X) containing an arbitrary anion atom or anion molecule by deprotection of the protecting group P of each secondary amine of the compound obtained by linking with the substituent G by coupling with the substituent G A compound in which two molecules of the target crown ether derivative represented by the following general formula (I) are bonded to each other by adding an ammonium salt Can Rukoto (Example 7).
X is an arbitrary anion atom or anion molecule composed of a part of sodium perchlorate, ammonium hexafluorophosphate, trifluoroacetic acid and the like. This is for dissolving the monomer for producing a non-covalent polymer in a non-polar organic solvent.
The reaction is carried out in a nonpolar solvent at a temperature ranging from 10 ° C to 40 ° C. Confirmation of the obtained product is performed by mass spectrometry and NMR.
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(I)
(In the formula, Q represents a substituent, and X represents any anion atom or anion molecule.)
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(II)
(In the formula, G represents a reactive substituent, and P represents a protecting group for a secondary amine.)
[0016]
The overall structure of the compound represented by the general formula (I) is a symmetrical structure in which a secondary ammonium salt is present at both ends and a cyclic molecule is linked to this, It is an effective substance for efficiently synthesizing a non-covalent polymer, because it can be strongly connected by a non-covalent bond without using a covalent bond.
[0017]
Examples of the compound of the general formula (I) include compounds having the following structural formula.
Furthermore, specifically, the compound represented by general formula (I) is demonstrated.
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[0018]
By dissolving the compound represented by the general formula (I) obtained in the above in a nonpolar solvent, a specific and strong interaction between the crown ether and the ammonium salt is caused to cause spontaneous association. And by self-assembly, a novel non-covalent assembly represented by the following general formula (IV) can be produced.
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(I)
(In the formula, Q represents a substituent, and X represents any anion atom or anion molecule.)
[0019]
【Example】
EXAMPLES Next, although an Example demonstrates this invention still in detail, this invention is not limited at all by these examples.
[0020]
Example 1
Under nitrogen, 250 ml of dimethylformamide was charged with 33.9 g (0.20 mol) of 2- [2- (2-chloroethoxy) ethoxy] -ethanol and 42 g (0.30 mol) of potassium carbonate and stirred at 100 ° C. (Bath temperature). A solution prepared by dissolving 13.8 g (0.10 mol) of 3,4-hydroxybenzaldehyde in 150 ml of dimethylformamide was added dropwise thereto.
The reaction was allowed to proceed overnight, followed by cooling and evaporation of the solvent by evaporation and drying under reduced pressure. Under nitrogen, 300 ml of dichloromethane (dehydrated), 37.3 g (0.37 mol) of triethylamine and 0.25 g (2.04 mmol) of dimethylaminopyridine were added and stirred at 0 ° C. (on an ice bath). A solution prepared by dissolving 57.19 g (0.30 mol) of paratoluenesulfonyl chloride in 600 ml of dichloromethane was added dropwise with vigorous stirring. After completion of the dropwise addition, the ice bath was removed, the reaction system was returned to room temperature, stirred for 1 hour, evaporated to evaporate the solvent, added with 300 ml of dichloromethane, and then saturated three times with 200 ml of 0.1 M aqueous hydrochloric acid, followed by saturation. Washed twice with 200 ml of aqueous sodium chloride solution. The organic phase was dried over magnesium sulfate (anhydrous), the solvent was distilled off, and the residue was purified by column chromatography (silica gel, methylene chloride / ethyl acetate = 100 / 0-50 / 50). 3,4-bis [2- (2- (2- (2-para-toluenesulfonyloxy) ethoxy) ethoxy) ethoxy] benzaldehyde Yield 24.19 g, Yield 35.41%
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(III)
[0021]
Example 2
7. 3,4-bis [2- (2- (2- (2- (2-toluenesulfonyloxy) ethoxy) ethoxy) ethoxy] benzaldehyde obtained in Reference Example 1 in 700 ml of dimethylformamide (for peptide synthesis) under nitrogen 43 g (11.4 mmol), (3,4-hydroxyphenyl) -acetic acid methyl ester (1.25 g, 11.4 mmol) and cesium carbonate (18.50 g, 56.8 mmol) were dissolved. The mixture was heated to 100 ° C. with stirring, and stirring and heating were continued for 3 days. Then, it returned to room temperature, filtered, and after removing cesium carbonate, it evaporated and the solvent was distilled off. 200 ml of toluene was added thereto, washed twice with 100 ml of 1N hydrochloric acid aqueous solution and once with 100 ml of distilled water, and then purified by column chromatography (silica gel, ethyl acetate) to obtain the following crown ether (IV). Yield 2.44 g, Yield 45.10%
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(IV)
[0022]
Example 3
To 100 ml of toluene (dehydrated) were added 5.56 g (10.4 mmol) of the crown ether derivative (IV) obtained in Reference Example 2 and 1.20 g (11.2 mmol) of benzylamine, and the mixture was stirred at 60 ° C. for 30 minutes. Thereafter, the solvent was distilled off. Further, 100 ml of toluene was added, and the mixture was similarly stirred at 60 ° C. for 30 minutes, and the solvent was distilled off. This operation was repeated twice. 100 ml of methanol (dehydrated) was added to the reaction product, and 2.8 g (74 mmol) of sodium borohydride was added little by little while stirring on an ice bath. After stirring for 1 hour, 2N hydrochloric acid was added to bring the reaction solution to pH 2. Methanol was distilled off and the aqueous solution was extracted with dichloromethane. The extracted solution was washed with a 10% aqueous sodium hydroxide solution, the organic layer was dried over magnesium sulfate, and the solvent was distilled off. Structural formula as crude product
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(V)
The crown ether derivative (V) represented by this was obtained.
[0023]
Example 4
The crown ether derivative (V) obtained in Example 3 was dissolved in 110 ml of methylene chloride (dehydrated), 3.34 ml (14.5 mmol) of di-tert-tildicarbonate, and 0.14 g (1. 2 mmol) was added and stirred at room temperature for 12 hours. The solvent was distilled off, and the resulting oil was purified by column chromatography (silica gel, ethyl acetate) to obtain the structural formula.
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(VI)
6.58 g (87%) of a crown ether derivative (VI) represented by
[0024]
Example 5
6.58 g (9.1 mmol) of the crown ether derivative (VI) obtained in Example 4 was dissolved in 250 ml of diethyl ether (dehydrated), and 1.3 g (34 mmol) of lithium aluminum hydride was stirred on an ice bath. ) Was added little by little. After stirring for 12 hours, 100 ml of 10% aqueous citric acid solution was added little by little, and the mixture was extracted with diethyl ether. The organic layer was dried over magnesium sulfate and the solvent was distilled off. Structural formula as crude product
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(VII)
Thus, 4.39 g (69%) of a crown ether derivative (VII) represented by the formula:
[0025]
Example 6
Under nitrogen, 0.141 g (0.72 mmol) of heptanedioyl dichloride, 1.0 ml of pyridine (dehydrated) and 1.0 g (1.43 mmol) of the crown ether derivative (VII) obtained in Example 5 were mixed with chloroform ( The mixture was dissolved in (dehydrated) and stirred at room temperature for 2 days. Dichloromethane was added to the reaction solution, which was washed with 1N hydrochloric acid and 10% aqueous sodium hydroxide solution. The organic layer was dried over magnesium sulfate, and then the solvent was distilled off. The resulting oily product is purified by column chromatography (Sephalex, methanol) to give the structural formula
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(VIII)
0.258 g (24%) of a crown ether derivative (VIII) represented by
Mass spectrometry value (C ₈₃ H ₁₁₀ N ₂ O ₂₄ As)
Calculated value: 1519
Actual value: 1541 (M + Na)
[0026]
Example 7
34.1 mg (0.022 mmol) of the crown ether derivative obtained in Example 6 was dissolved in 0.6 ml of chloroform, 25.5 ml (0.22 mmol) of trifluoroacetic acid was added, and the mixture was stirred for 3 days. Dichloromethane was added to the solution, washed with a 10% aqueous sodium hydroxide solution, and the organic layer was dried over magnesium sulfate. This is dissolved in chloroform, equimolar trifluoroacetic acid is added, and the structural formula is
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(IX)
Thus, the compound (IX) represented was obtained.
[0027]
【The invention's effect】
According to the present invention, a crown ether obtained by reacting a compound in which NH of a crown ether derivative compound containing dibenzo-24-crown-8-ether and a secondary amine is protected with a protecting group and linking two compounds together. A compound obtained by bonding two molecules of a derivative and binding two molecules of a novel crown ether derivative represented by the general formula (I), which is a compound obtained by deprotecting a protecting group, can be obtained, This compound spontaneously polymerizes in a nonpolar solvent, and becomes a raw material which can easily produce a non-covalently bonded polymer.

Claims (2)

A compound obtained by binding two molecules of a crown ether derivative, which is represented by the following general formula (I).
(In the formula, Q represents —CH ₂ OC (═O) —LC (═O) OCH ₂ —, L represents an alkylene group, and X represents any anionic atom or anionic molecule. .) It is obtained after reacting a crown ether derivative compound consisting of dibenzo-24-crown-8-ether represented by the following general formula (II) and a secondary amine together with a compound represented by the general formula A-LA. And deprotecting the compound, and adding a compound containing any anion atom or anion molecule to produce a compound in which two molecules of the crown ether derivative represented by the following general formula (I) are bound. A method for producing a compound in which two molecules of a crown ether derivative are bonded.
(In the formula, G represents a group which reacts with the compound A-LA to form Q in the general formula (I), and P represents a protecting group for a secondary amine.)
[Chemical 3]
A-LA
(In the formula, A is a group that reacts with the reactive substituent G of the general formula (II) to form —CH ₂ OC (═O) —, and L is an alkylene group.)
(In the formula, Q represents —CH ₂ OC (═O) —LC (═O) OCH ₂ —, L represents an alkylene group, and X represents any anionic atom or anionic molecule. .)