TW201040211A - Imidazolium-based poly(ionic liquid)s and method to prepare the same - Google Patents

Abstract

This invention provid a novel poly(ionic liquid)s and method for producing the same. The poly(ionic liquid)s which is showed as formula(I), where the symbols R1 or R2 or R3 or X1, and m are defined as the same as claims and description.

Description

201040211 VI. Description of the Invention: [Technical Field] The present invention relates to a polymer and a preparation method thereof, and particularly to an ionic liquid polymer and a preparation method thereof [Prior Art] An ionic compound composed of a positively charged organic cation and a negatively charged organic or inorganic anion. Since the ionic liquid has the characteristics of no vapor pressure, no flammability, no ignitability, and high thermal stability, it can be used for high production processes. Safety and avoidance of environmental pollution caused by the use of general volatile organic solvents, therefore, ionic liquids have become a green solvent that has attracted attention in recent years. In recent years, research on high molecular weight polyionic liquids combined with ionic liquids and polymer properties has also received increasing attention. For example, in "Tuning the solubility of polymerized ionic liquid by simple anion-exchange reactions" (Polym. Sci. Part A: Polym. Chem., 2004, 42, 208), Marcilla, R., et al. The ionic liquid monomer of l-Vinyl-3-alkylimidazolium bromide is polymerized to obtain a polyimidazolium salt as shown in the following formula (1).

R=C2H5 or C4H9, Z=Br, PF6, CF3S〇3, (CF3S〇2)2N, or 3 201040211

(CF3CF2S02) 2N and through the test results, it is known that these polyimidazolium salt ions produce different solubility in solution under the coordination of different anions.

In addition, in "Low-pressure C〇2 absorption in ammonium-based poly(ionic liguid)s" (Polymer 2005, 46, 12460) - Tang, J_, et al., using ionic liquid monomers to synthesize the following formula (2) A comb-type polyionic liquid polymer as shown, and this type of polyionic liquid polymer material has been experimentally found that the adsorption amount of carbon dioxide can reach l〇.67 mole%.

In "Synthesis of molten salt-type polymer brush and effect of brush structure on the ionic conductivity" (Electrochimica Acta, 2001, 1723) - Yoshizawa, M., et al. use free radical polymerization of ionic liquid monomers. In response, a polyionic liquid polymer material as shown in the following formula (3) was developed.

R=CH3, C2H5, Z=a, Br, (CF3S02)2N 4 201040211 These polyionic liquid polymers have been tested and found to have good ionic conductivity. From the above literature, it is known that imidazole The salt polyionic liquid polymer is mainly formed by a free radical polymerization of a taste-salt polymerized monomer having a vinyl group or an acrylic group to form a comb-like polyimidazolium salt ionic liquid polymer, and the polyionic liquid polymer is It has the ability to adsorb C〇2, has good ionic conductivity, and can change the polarity of polyionic liquid polymer by the change of anion, and has a wide range of uses. Therefore, how to develop novel and more diverse polyionic liquid polymers to provide research and development of related technologies has been the subject of continuous research and development in the technical field. SUMMARY OF THE INVENTION The purpose of this month is to provide a novel taste beta-salt polyionic liquid polymer. Further, another object of the present invention is to provide a method for preparing an imidazolium salt polyionic liquid polymer which is simple in process and easy to control. , the present invention - the species (4) salt polyionic liquid polymer comprises a chemical formula represented by the formula (I),

Ri wherein R1, I, and I are each independently a hydrogen atom, a monovalent alkyl group of c cio, or one of 4 and a human, V---"C1~C20 monovalent alkyl group, (ch2ch2o)p, 5 201040211 ( CH2CH2CH2〇)q, and (R4〇R5)s, where pq is not greater than ι〇, h, I are monovalent alkyl groups selected from C1 to C10, respectively, and the product of the sum of carbon numbers of 仏 and ^ and s Not more than 3 〇 U is represented by a prime element and ❿ is not less than 3. Another object of the present invention is to provide a method for producing a polymer of a sodium salivium salt polyionic liquid as shown in the above formula (1), comprising the steps of: (a) preparing an imidazole having a chemical structure represented by the following formula (11): Monomer, 〇

(II) wherein Ri, R2, and R3 are each a hydrogen, a C1 to C1 () monovalent alkyl group, or a combination thereof, and a γ table is not a c1 to C2 〇 unit price base, an elevation of 2 〇), (CH2CH2CH2 〇)q, and (R4〇R5) one of them, pq is not more than 1〇, 〇R4, R5 are monovalent alkyl groups selected from C1 to C10, respectively, and the sum of the carbon number of the heart and r5 and S is not More than 30, \ represents a functional element; (8) The above-mentioned quinone monomer is subjected to self-polymerization under a predetermined reaction condition to obtain the polymer having the chemical structure (IV) as shown in the above formula (1). The invention has the advantages that the imidazole monomer having a dentate substitution at the end can be obtained by self-polymerization, and the main chain type imidazolium salt polyionic liquid polymer having novel structure can be obtained, which is simple and easy to control, and can be obtained. An imidazolium salt polyionic liquid polymer having a good degree of polymerization. 6 201040211 [Embodiment] In view of the rapid application and development of polyionic liquid polymers, the development of related polyionic liquid polymer materials still cannot provide more diverse selection and application by researchers in related fields. The inventors have devised a structure different from the conventional polyionic polymer, and the polyionic polymers of these different structures are expected to provide a more diverse material selection for researchers in the field of related polyionic polymers. In the present invention, the inventors perform a substitution reaction with a reaction group having a different dentin substitution with an amino group to obtain a taste-salt monomer having a different substituent group, and then separately perform the respective imidazole monomers. After the polymerization reaction, a main chain type rice salt polyionic liquid polymer different from the conventional comb-like imidazolium salt polyionic liquid polymer structure can be obtained, and the polymerization method is simple and the polymerization degree is high, so that the related polyion can be obtained. The field of application of polymers provides a more diverse and cost-effective imidazolium salt polyionic liquid polymer material. The method of the present invention for preparing a Sheim salt salination polyionic liquid is also the following two steps. (a) First, an imidazole group having a chemical structure represented by the following formula (A) and a reactant having a chemical structure different in halogen substitution as shown in the formula (B) are prepared, and the substitution is carried out under a base reaction condition. The reaction is carried out to obtain an oxazole monomer as shown in the formula (11). Preferably, the basic reaction condition can be selected from the group consisting of sodium hydroxide (Na〇H), sodium methoxide (CH3〇Na), and ethoxylation. Sodium (C^HsONa), sodium hydride (NaH), hydrogenation (UH), or a combination of these, the reaction mechanism is as follows: (II) 201040211 r3 (B) XrY-X2

, NH γ R1 (A) R:

Ri

O wherein R, R2, and R3 are each independently a hydrogen, a C1 alkyl group, or a combination thereof, X, X2 are each selected from a halogen, and may be the same or different, and Y is a unit price selected from C1 to C20. One of alkyl, (CH2CH20)p, (CH2CH2CH20)q, and (R4OR5)s, p, q is not more than 10, R4, R5 are monovalent alkyl groups selected from Cl~CIO, respectively, and R4 and R5 The product of the sum of carbon numbers and s is not more than 30. (b) The imidazole monomer is subjected to self-polymerization under room temperature or under heating reaction conditions to obtain an imidazolium salt polyionic liquid polymer represented by the formula (I). ❹

Γ-hxi (I) Specifically, the step (a) is to prepare a microphone first. a first mixed solution of a sitting group (A) with a tetrahydrofurane (hereinafter referred to as thf) solution, a second mixed solution of LiH and an anhydrous THF solution, and a solution of the reactant (B) and anhydrous THF Forming the third mixed liquid, then, 8 201040211, slowly adding the first mixed liquid to the second mixed liquid under nitrogen, disturbing for a period of time to form an intermediate reaction liquid, and then slowly adding the third mixed liquid to the middle In the reaction mixture, the reaction is continued for a while, and then the reaction is stopped by adding water. Then, the THF is removed by concentration under reduced pressure, and then the organic solvent is added for extraction. The organic layer is washed with a saturated aqueous solution of the salt to remove impurities, and the residue is removed by anhydrous magnesium sulfate. The water in the organic layer is finally removed by concentration under reduced pressure to obtain a high-purity imidazole monomer as shown in the formula (II). Preferably, the reactant (B) is a bis-substituted compound selected from C2 to C10, and the reactant (B) suitable for use in the preferred embodiment of the present invention is selected from the group consisting of a dihalogen-substituted C3. a C6-halogenane compound, the imidazole group (A) is selected from the group consisting of imidazole, and the reaction temperature of the step (4) is from room temperature to the reflux temperature of the organic solvent used. The self-polymerization reaction in the step (b) can be carried out under solvent-free conditions or solvent conditions, and the following methods 1 and 2 are respectively described. Method 1 (solvent-free polymerization): The imidazole monomer represented by the formula (II) is placed in a reaction flask, and after reacting for 1 to 7 days at 60 to 120 ° C, acetone is added to obtain an imidazole obtained by self-polymerization. The salt polyionic liquid polymer is precipitated and filtered, and then the precipitate obtained by filtration is washed and dried to obtain a high-purity main chain type oxazole salt polyionic liquid polymer represented by the formula (I). Method 2 (solution polymerization): adding an imidazole monomer represented by the formula (II) and a polar solvent to a reaction flask to obtain a reaction liquid. The reaction solution is reacted at a reflux temperature of the polar solvent for 1 to 7 days. The main chain type imidazolium salt polyionic liquid polymer can be obtained, and its polar solvent can be selected from organic solvents having good molecular solubility for the imidazole monomer and the imidazolium salt polyionic liquid, for example, 9 201040211 , ο : methanol, ethanol, ethylene glycol, monomethyl methamine, dimethyl acetamide, dimethyl hydrazine, or a combination of one of them 'so that after the completion of the polymerization reaction, acetone can be added. The imidazolium salt polyionic liquid polymer obtained by the polymerization reaction is precipitated and filtered, and then the transferred tank is washed and dried with acetone to obtain a main chain type imidazolium salt polyionic liquid of the purity shown in formula (1). a polymer; or may be selected from the same. The solubility of the monomer is good, but the solvent of the poly-molecular liquid of the m-salt polyionic liquid, such as ethyl acetate, acetone, or THF, can be used as a monomer in the rice. In the self-polymerization process, the two molecules of the salivary salt polyionic liquid obtained by the polymerization are directly deposited on the solvent towel, and then filtered and washed with propylene to obtain a salicyl salt polyionic liquid polymer as shown in the formula (1). It is worth mentioning that 'when the polar solvent used in the self-polymerization reaction is used, the higher the reaction temperature can be, the higher the reaction temperature can be. The better the poly-α degree of the high-knife syrup is obtained. The embodiment of the step (9) is carried out from the polymerization reaction, the method 2, and the organic solvent is selected from the group consisting of decyl alcohol, ethanol, and ethylene glycol. This month will be described in the following seven specific examples, but special 月i| used in the present invention for polymerization to obtain a miso salt polyionic liquid high knife, the Migui group (4), reaction The substance (B), and the miso monomer (II), the structure thereof is not limited thereto, and (d) should be construed as limiting the practice of the invention. The structures of the stilbene group (4), the reactant (8), and the stilbene monomer used in the specific examples 1 to 7 of the present invention are simply summarized in Table 1. 10 201040211 Table 1 oxime group (A) Reactant (B) Imidazole monomer (Π) Specific Example 1 to 2 / \ nV/nh . Cl Specific Example 3 to 5 Specific Example 6 Specific Example 7 Γ=\ &lt Specific example 1 >

This step (a) was first carried out. 'The odor 0 sitting group (A) (Imidazole, 3.46 g, 0.05 mole) was added to 5 mL of anhydrous THF to form a first mixture, which was placed in an ice bath, and then LiH (0.5 g, 0.06) was taken. Mole) 5 mL of anhydrous THF was added to form a second mixed liquid, and the first mixed liquid was slowly added to the second mixed liquid under nitrogen to obtain an intermediate reaction liquid, and stirring was continued for 1 hour, followed by further reacting the reactants (B). (l-bromo-3- chloropropane, 5.0 g, 0.032 mole) was mixed with anhydrous THF to obtain a third mixture, and the third mixture was slowly added to the intermediate reaction solution, and reacted under nitrogen for 24 hours and then terminated with water. The reaction was carried out, and the THF was extracted with a vacuum concentrator, and then extracted with dichloromethane (50 mL×3), and 11 201040211 machine layer was taken to dissolve the water-soluble impurities by saturated brine, and then the water was removed with anhydrous magnesium sulfate. The pressure-concentration removes the dichloromethane to obtain a transparent viscous imidazole monomer (II). Then, the step (b) is carried out, and the above-mentioned sodium saponin monomer (I) (6·5 g, 0.045 m〇le) is taken, and methanol (15 mL, 3 Torr) is added, and the mixture is heated at the reflux temperature of “~chuanyi”. After stirring for 7 days, the reaction was cooled to room temperature, and the reaction solution was slowly dropped into 300 mL of acetone (at least 20 times the volume of methanol), that is, the white powder was sedimented, and the white powder was washed 3 times with acetone after filtration. Thereafter, after concentration under reduced pressure and vacuum drying, an imidazoline polyionic liquid as shown in Formula M can be obtained.

<Specific Example 2> The method for producing the imidazolium salt polyionic liquid polymer of Specific Example 2 of the present invention is the same as the imidazole group and the specific example i, except that the self-polymerization step is carried out by using ethylene glycol. It is an organic solvent, and the polymerization temperature is controlled to be stirred at 1 ° C for 1 day, thereby obtaining an imidazolium polyionic liquid host molecule as shown by the above formula M. <Specific example 3 >

Add the first mixture of 5 mg of anhydrous THF to Imidazole, and place it in an ice bath, then add LiH (〇22 g, 0.028 mole) to 5 mL·anthracene. THF forms a second mixture, and the first mixture is slowly added to the second mixture under nitrogen at 12 201040211 to form an intermediate reaction solution' and stirring is continued for 1 hour, and then the reactants are further

(B) (l-br〇mo-4-chl〇r〇butane '2.5 g, 〇.015mole) is mixed with anhydrous THF to form a third mixed liquid, and the third mixed liquid is slowly added to the intermediate reaction liquid. And reacting under nitrogen for 24 hours, then adding water to terminate the reaction, removing the THF with a vacuum concentrator, extracting with di-methane (5 〇 mL x 3), taking the organic layer to saturate the brine to remove the water-soluble impurities, and then Anhydrous magnesium sulfate removes water, most

After removing the dioxane by a vacuum concentrator, a transparent viscous imidazole monomer (II) is obtained. Then take the above-mentioned monomer (11) (8.36 g, 〇. 〇 53 mole), add 17.5 mL of methanol to reflux at 65~70 ° C under reflux, and cool to room temperature after 7 days. The solution of the reaction is slowly dropped into 3 〇〇mL of acetone (at least 20 times the volume of methanol), that is, the white powder is sedimented, and after the transition, the white powder is washed three times with acetone, and then concentrated under reduced pressure, vacuum. After drying, an imidazolium salt polyionic liquid polymer as shown in Formula 1-2 can be obtained.

<Specific Example 4> The method for producing an imidazolium salt polyionic liquid polymer of Specific Example 4 of the present invention has a reactant and an imidazole group substantially the same as in the specific example 3, except that the self-polymerization step is carried out by using ethanol as a solvent. The organic solvent and the polymerization temperature are controlled to be heated under reflux at a reflux temperature of 70 to 80 ° C for 2 days to obtain an imidazolium salt polyionic liquid polymer as shown in the above formula 1-2. 13 201040211 <Specific Example 5> The present invention specifically {the method of preparing the column salt polyionic liquid polymer of the column 5, the reactant and the (4) base circle are substantially the same as the specific example 3, except that the self-polymerization step is performed. When ethylene glycol is used as an organic solvent, and the polymerization temperature is controlled to be heated and stirred at the reaction temperature of HHTC for a day, a miso salt polyionic liquid polymer as shown in the above formula can be obtained. <Specific Example 6 > First, the step (3) was carried out, and an imidazole group (A) (Imidaz〇le, 83 g, 0.027 m〇le) was added to 5 mL of anhydrous THF to form a first mixture and placed in an ice bath. Then take LiH (0.26 g, 〇.〇33mole) into a 5 ml anhydrous THF to form a second mixture, and slowly add the first mixture to the second mixture under nitrogen to form an intermediate reaction solution, which continues. Stir for a few hours; mix the reactant (B) (l-br〇mo-5_chlor〇pentane, 25 g, (4) (9) with (4) and anhydrous THF, and then slowly add the third mixture to the intermediate reaction solution. In the middle of the reaction, the reaction was stopped by adding water for 24 hours. The THF was removed by a vacuum concentrator, and then dioxane (5 〇 mL x 4) was added for extraction. The organic layer was taken to saturate the brine to remove water-soluble impurities. Then, the water is removed by anhydrous magnesium sulfate, and finally the dioxane is removed by a vacuum concentrator to obtain a transparent viscous imidazole monomer as shown by the formula π. Next, the step (b) is taken. The above-mentioned oxime monomer I (gw gram, 〇.〇52m〇le) is added to HmL methanol and placed at a reflux temperature of 65_7 〇t. After heating and stirring for 7 days, it was cooled to room temperature, and the solution of the reaction was slowly dropped into propylene-300 mL (at least 2 〇 volume of sterol), that is, white powder/children were dropped, and then filtered and washed with acetone. After 3 times of white powder, concentrated under reduced pressure, and then dried at 14 201040211, the imidazolium polyionic liquid polymer as shown in formula _3 can be obtained.

<Specific Example 7> First, the β-thumb step (a) 'takes rice. The sitting group (A) (imidazole, 1.83 g, 0.027 mole) was added to 5 mL of anhydrous Thf to form a first mixture, which was placed in ice/valley, and then LiH (0.26 g, 〇.〇33mole) was added to 5 mL of anhydrous THF to form a first Mixing the solution, slowly adding the first mixture to the second mixture under nitrogen fluoride to form an intermediate reaction solution, and continuously stirring for a few hours;

(B) (l-bromo-6-chlorohexane, 2.5 g, 0.0134 mole) was mixed with anhydrous THF to obtain a third mixed liquid, and the third mixed liquid was slowly added to the intermediate reaction liquid, and then under nitrogen. After the reaction for 24 hours, the reaction was terminated by adding water; the THF was removed by a reduced pressure concentrator, and then extracted with di-methane (5 〇mL×4), and the organic layer was taken to dissolve the water-soluble impurities with saturated brine, and then the water was removed with anhydrous magnesium sulfate. Finally, after removing the dioxane methane by a vacuum concentrator, an imidazole monomer having a transparent viscosity as shown in the formula can be obtained. Then, the step (b) is carried out, and the above-mentioned oxime monomer η (8.97 g, 0.052 mole) is added to 17 mL of ethylene glycol, and the mixture is heated and stirred at room temperature for 1 day at rc, and then cooled to room temperature. Then, the solution of the reaction is slowly dropped into C-300 mL (at least 2 times the volume of methanol), that is, the white powder is sedimented, and after filtering, the white powder is washed three times with acetone, and then concentrated under reduced pressure, vacuum. Drying, the imidazolium salt polyionic liquid 15 as shown in the formula!_4 is obtained. 201040211 Polymer. Referring to Fig. 1 to Fig. 7, Fig. 7 to Fig. 7 are the imidazolium salt polyionic liquid polymers of the specific examples 1 to 7, respectively. NMR spectroscopy. Ο Ο Inventors refer to jCSalamone in the paper (Macromolecules 3, 707, 1970) for the 'hi_nmr spectrum to integrate the Η on the acridine group in the pyridine-based polyionic polymer with the pyridine The method for estimating the degree of polymerization of the polymer of the polyionic polymer of the polyionic polymer, the method for estimating the degree of polymerization of the polymer, the NMR spectrum of the imidazolium salt polyelectrolyte in the nuclear magnetic resonance spectrum of FIG. Measured imidazole group The ratio of the integral value of Η(3·6 to 3.7 ppm) to the integral value of Η(4.2 to 4.4 ppm) on carbon, and the degree of polymerization of the specific examples i to 7 is estimated, and the calculation results of the above polymerization degree are compiled. Table II.

From the above results, it is understood that the present invention is not only simple in process, easy to control, but also has an increase in the boiling point of the organic solvent selected for the polymerization. In addition, it is worthwhile to mention that the polarity of the corresponding imidazolium polyionic liquid polymer will be relatively affected after the anion exchange changes the anion species. The solubility of the imidazolium polyionic liquid polymer (1-1~1-4) in different solvents after different anion substitutions is simply summarized in Table 3; since the anion exchange method is an experimental method commonly used in the technical field, Therefore, we will not repeat them here. Table 3

Sample Z' h2o EtOAc MeOH DMSO CH2C12 Toulene Acetone THF C1 + - + + - - - 1-1 pf6 - - + - - - *NTf2 - - - + - + Cl + + + - . - 1-2 pf6 - - - + - - + - *NTf2 - + - - + - Cl + + + - - - - 1-3 pf6 - - - + + *NTf2 - - + + - + Cl + + + - 1-4 pf6 - - + - - + - *NTf2 - - + + - - + -

+ : soluble, -: insoluble *: NTf2 = (CF3S02) 2N It is known from the results of Table 3 that the imidazolium polyionic liquid polymer of the present invention can be used in 2010 201011, which allows the mice to undergo pro-ion exchange reaction. Hydrophobic change The azole salt polyionic liquid polymer is suitable for different uses. Self-polymerization a: i^ This month, the use of iv-type monomers substituted with dentate, self-polymerization of the e-square cut main chain type (four) (four) ions (four) polymer structure and simple process, easy to control, in addition, through The anion exchange is adjustable. The polarity of the salt polyionic liquid polymer of the present invention is controlled, and the ruthenium can be more widely applied to the field of (4), so it is expected to cost the invention.

The above-mentioned ones are only the preferred embodiments of the present invention*, and the scope of the present invention cannot be limited thereto, that is, the simple scope of the invention according to the invention, and the simplicity of the invention. Equivalent variations and modifications are still within the scope of the invention. BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a nuclear magnetic resonance spectrum diagram illustrating a nuclear magnetic resonance spectrum of an imidazolium salt polyionic liquid polymer prepared by the specific example i; FIG. 2 is a nuclear magnetic resonance spectrum diagram illustrating the specific The nuclear magnetic resonance spectrum of the imidazolium polyionic liquid polymer prepared in Example 2; FIG. 3 is a nuclear magnetic resonance spectrum diagram illustrating the nuclear magnetic resonance spectrum of the imidazolium salt polyionic liquid polymer prepared by the specific example 3; 4 is a nuclear magnetic resonance spectrum showing the nuclear magnetic resonance spectrum of the π-salt polyionic liquid polymer prepared by the specific example 4; FIG. 5 is a nuclear magnetic resonance spectrum diagram illustrating the preparation of the specific example 5. The NMR spectrum of the salt I ionic liquid polymer; FIG. 6 is a nuclear magnetic resonance spectrum chart illustrating the nuclear magnetic resonance spectrum of the salt-concentrating polyionic liquid polymer prepared by the specific example 6; 18 201040211 FIG. 7 is a nuclear magnetic resonance spectrum showing the nuclear magnetic resonance spectrum of the imidazolium salt polyionic liquid polymer prepared by the specific example 7. [Main component symbol description] None

19

Claims (1)

201040211 VII. Scope of Application for Patent·· 1. An imidazolium salt polyionic liquid polymer having the chemical formula shown in formula (1): 2. 3. wherein, R1, R2, and R3 are each a hydrogen, a C1-C10 monovalent alkyl group, or a combination thereof, and Y represents a monovalent alkyl group of C1-C2〇, (CH2CH2〇)p, (CH2CH2CH2〇)q. And one of (R4〇R5)s, P, q is not more than 10' r4, r5 is a monovalent alkyl group selected from ci~C10, respectively, and the product of the sum of the carbon numbers of the rule 4 and Rs and S is not more than 30, Xl represents a pixel element, and m is not less than 3. The imidazolium salt polyionic liquid polymer according to the scope of the patent application, wherein Z is ci, Br, I, BF4, PF6, N(S〇3CF3)2, or n(cf3cf2so2)2. A method for preparing a polyazo liquid polymer of the azole salt salt represented by the chemical formula (1) according to the first aspect of the patent application, comprising the steps of: (a) preparing an imidazole monomer having the formula (11), Wherein, Ri, R2, and R3 are each a hydrogen atom, a monovalent alkyl group of Cl~cl〇, 20 201040211 or a combination thereof, and Υ represents a single compensation base of CI~C20, (CH2CH2〇)p, (CH2CH2CH2〇)q And (R4〇R5)s, or one of them, wherein P and q are not more than 10, and R4 and r5 are each a monovalent alkyl group selected from C1 to C10, and the sum of carbon numbers of R4 and R5 and s The product is not more than 3 〇, and Χι denotes a halogen element; and - (b) (d) The monomer of the (4) step (4) is subjected to a self-polymerization reaction under the reaction condition of __, and the (4) body height as shown in the formula (1) can be obtained. molecule. 4. According to the preparation method of the patent application specification, wherein 5. the preparation method according to the patent application specification is carried out under conditions. The imidazolium salt polyionic liquid polymer described in the above 3 is a polymerization step which is carried out without a solvent. The imidazole salt polyionic liquid polymer 5 〇 〇 3 — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — 咪唑 咪唑 咪唑 咪唑, where the polymerization The solvent used for ethanol, ethylene glycol, and dimethyl is selected from the group consisting of methanol, melamine, dimethylacetamide, dimethyl sulfoxide, ethyl acetate, or tetrahydrofuran. Methyl 21