CN108676173B - Polyion liquid with ionic bond as framework and preparation method thereof - Google Patents
Polyion liquid with ionic bond as framework and preparation method thereof Download PDFInfo
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Abstract
The invention provides polyion liquid taking an ionic bond as a framework and a preparation method thereof. The polyion liquid taking ionic bonds as a framework is characterized by having the following structural formula:
Description
Technical Field
The invention relates to a novel polyion liquid, in particular to a preparation method of a novel polyion liquid taking an ionic bond as a framework.
Background
The ionic liquid is a salt which is liquid at normal temperature and consists of anions and cations. Ionic liquids exhibit unique physicochemical properties as a liquid organic salt: the vapor pressure at normal temperature is almost zero; high solubility to organic, inorganic and organic metal substances; the thermal stability is high; good ion conductivity and the like. The ionic liquid draws wide attention in the application aspects of green solvents, catalytic reaction of fine chemistry, material separation methods, electroanalysis, emerging nano biotechnology and the like. Polyionic liquids, which may also be referred to as ionic macromolecules, are macromolecules having repeating units that contain pairs of anions and cations of the ionic liquid. The ions in the polyionic liquid are fixed on the chain segment, but the properties of the polyionic liquid can be maintained, and the characteristics of the high polymer and the ionic liquid are combined. The polyion liquid has strong designability, and the structure and the composition of a macromolecular chain, the position of an ion pair on the molecular chain and the density of ions can be controlled except the structure and the types of anions and cations. By designing the structure of the polyion liquid, a large amount of novel functional polyion liquid can be obtained, and the polyion liquid can be applied to the aspects of dispersing agents, phase transfer agents, adsorbents, separating agents, ion conductive materials, nano composite materials, biomedical materials and the like.
A novel polyion liquid using ionic bond as a framework. At present, polyion liquid is mainly connected by covalent bonds, ions are suspended on a main chain in a functional group form, and are connected by utilizing the interaction between anions and cations, and the polyion liquid taking the ionic bonds as a framework is not reported yet. With the deep research of the theory of polyion liquid and the development of application technology, the structure and performance of polyion liquid need to be finely designed according to the requirements, and more novel functional polyion liquid materials with excellent performance are synthesized. The design and synthesis of novel polyion liquid taking ionic bonds as frameworks have positive significance for enriching the types of polyion liquid, researching the structural performance relationship and developing new functional application of the polyion liquid.
Through the search of the existing documents, the polyion liquid is mainly prepared by the methods of traditional free radical polymerization, active free radical polymerization, cationic polymerization and the like. Green et al published "Alkyl-substituted N-Vinylimidazolium polymeric compositions" Macromolecular chemistry and physics "2011 Vol 212-page 2522-page 2528: thermal properties and ionic compositions ", which are directly subjected to free radical polymerization to synthesize a series of imidazole polyionic liquids with alkyl substituents of different lengths. Texer et al published "Triblock Copolymer Based on Poly (1- [ 11-acryloylundecyl") and Poly (1- [11-acryloylundecyl ") at 33 volumes 69-74 of" Macromolecular Rapid Communications "2012]-3-methyl-imidozolium bromide) ", which was synthesized by Atom Transfer Radical Polymerization (ATRP) of ionic liquid monomer at 60 ℃ using a macroinitiator PPO-diOH with hexamethyltriethylenetetramine-copper bromide complex as a catalyst, to synthesize polyionic liquid named Poly (ILBr-b-PO-b-ILBr). Zhang et al published a "cationic polymerization of p-methyl type in selected ionic liquids and a cationic polymerization mechanism" in an ionic liquid "at Polymer Chemistry, 2016, volume 7, page 5099-5112, by OMIM][BF4]In the method, isobutyl vinyl ether is subjected to cationic polymerization at 0 ℃, and a series of polyion liquid is synthesized by using a plurality of auxiliary initiators. Polyionic liquids with different structures can be prepared by using different polymerization methods. However, at present allThe polyion liquid is connected by covalent bonds, and is connected by utilizing the interaction between anions and cations, and the polyion liquid taking ionic bonds as a framework is not reported yet.
Disclosure of Invention
The invention aims to expand the variety and structure of polyion liquid and obtain polyion liquid taking ionic bonds as a framework by applying molecular design.
In order to achieve the above object, the present invention provides a polyion liquid with an ionic bond as a skeleton, which is characterized in that the structural formula is as follows:
wherein n is 150-180.
The invention also provides a preparation method of the polyion liquid taking the ionic bond as the skeleton, which is characterized by comprising the following steps: 1, 4-dibromobutane and N-methylimidazole are used as raw materials, and the raw materials are subjected to quaternization reaction to synthesize 1, 4-dimethylimidazolebutane (shown as a formula (1)); synthesizing DEDBS (shown as a formula (2)) by carrying out alcoholysis reaction on 1, 12-dodecanediol and o-sulfobenzoic anhydride; and finally, mixing the aqueous solution of the 1, 4-dimethyl imidazole butane with the aqueous solution of the DEDBS, and spin-drying water to obtain the novel polyion liquid (shown as a formula (3)) with the ionic bond as a framework.
The invention also provides a preparation method of the polyion liquid taking the ionic bond as the skeleton, which is characterized by comprising the following steps:
step a: carrying out water removal and oxygen removal treatment on the reaction container;
step b: adding 1, 4-dibromobutane and N-methylimidazole into a reaction vessel under the protection of nitrogen, heating and stirring for reaction to obtain 1, 4-dimethylimidazole butane;
step c: b, cooling the 1, 4-dimethyl imidazole butane obtained in the step b to room temperature, and then adding acetone for washing;
step d: c, rotationally evaporating the 1, 4-dimethyl imidazole butane obtained in the step c in vacuum to remove acetone;
step e: d, dissolving the 1, 4-dimethyl imidazole butane obtained in the step d in deionized water to obtain an aqueous solution of the 1, 4-dimethyl imidazole butane;
step f: putting 1, 12-dodecanediol and o-sulfobenzoic anhydride into toluene, heating, stirring and refluxing to obtain a DEDBS toluene solution;
step g: cooling the solution obtained in the step f, taking the supernatant, performing vacuum spin drying, and dissolving in deionized water to obtain an aqueous solution of DEDBS;
step h: mixing the aqueous solution of 1, 4-dimethyl imidazole butane with the aqueous solution of DEDBS, spin-drying, and vacuum-drying to obtain the novel polyion liquid with the ionic bond as the skeleton.
Preferably, the molar ratio of 1, 4-dibromobutane to N-methylimidazole in the step b is 1: 2.5-3.
Preferably, the reaction temperature in the step b is 50-80 ℃.
Preferably, the reaction time in step b is 8 to 12 hours.
Preferably, in the step c, after the 1, 4-dimethyl imidazole butane obtained in the step b is cooled to room temperature, acetone is added for washing for 2-3 times, then the reaction product is broken up, and the mixture is subjected to ultrasonic treatment in the acetone for 15-30 minutes.
Preferably, the vacuum rotary evaporation temperature in the step d is 40-60 ℃.
Preferably, the concentration of the 1, 4-dimethyl imidazole butane solution in the step e is 0.5-1 mol/L.
Preferably, the molar ratio of the 1, 12-dodecanediol to the o-sulfobenzoic anhydride in step f is 1: 2.5-3.
Preferably, the temperature of the oil bath in the step f is 120-140 ℃.
Preferably, the reaction time in step f is 8 to 12 hours.
Preferably, the vacuum rotary evaporation temperature in the step g is 70-90 ℃.
Preferably, the concentration of the aqueous solution of DEDBS in the step g is the same as that of the aqueous solution of 1, 4-dimethyl imidazole butane.
Preferably, the rotary evaporation temperature in the step h is 70-90 ℃, the vacuum drying temperature is 70-90 ℃, and the time is 1-2 days.
The principle of the invention is that 1, 4-dibromobutane and N-methylimidazole are used as raw materials to synthesize 1, 4-dimethylimidazole butane through quaternization. Then, DEDBS is synthesized by alcoholysis reaction of 1, 12-dodecanediol and o-sulfobenzoic anhydride. An aqueous solution of 1, 4-dimethylimidazolidenebutane was mixed with an aqueous solution of dedss. Due to the interaction between imidazole cations and sulfonic acid anions, the two small molecules form linear macromolecular polyion liquid. And finally, removing hydrogen bromide by vacuum spin drying to obtain pure novel polyion liquid taking ionic bonds as a framework. The structure of the obtained novel polyion liquid with the ionic bond as the framework can be detected by a nuclear magnetic resonance hydrogen spectrum, and an infrared spectrum, a gel permeation chromatogram, a differential scanning calorimetry, a thermal weight loss and the like are taken as auxiliary analysis means.
Compared with the prior art, the invention has the beneficial effects that:
the novel polyion liquid prepared by the method has a structure which is greatly different from that of the traditional polyion liquid. At present, polyion liquid is mainly connected by covalent bonds, ions are suspended on a main chain in a functional group form, and are connected by utilizing the interaction between anions and cations, and the polyion liquid taking the ionic bonds as a framework is not reported yet. The polyion liquid prepared by the invention and taking the ionic bond as the framework has positive significance for enriching the types of the polyion liquid, researching the structure performance relationship and developing new functional application of the polyion liquid.
Drawings
FIG. 1 is a nuclear magnetic spectrum of a novel polyion liquid with ionic bonds as a framework prepared by the method;
wherein, fig. 1a, b, c respectively correspond to the one-dimensional nuclear magnetic hydrogen spectra of the novel polyion liquid prepared in examples 1, 2, 3 and using ionic bonds as the skeleton.
FIG. 2 is a Fourier infrared spectrum of the novel polyion liquid with ionic bonds as frameworks.
FIG. 3 is a differential scanning calorimetry spectrogram of the novel polyion liquid with ionic bonds as frameworks.
FIG. 4 is a thermogravimetric curve of the novel polyionic liquid with an ionic bond as a framework prepared by the invention.
FIG. 5 shows the molecular weights of the novel polyion liquids prepared in examples 1, 2 and 3 and having ionic bonds as frameworks, and the corresponding n value test results.
Detailed Description
In order to make the invention more comprehensible, preferred embodiments are described in detail below.
Example 1
The polyion liquid with ionic bonds as the frameworks has a structural formula shown as a formula (3), wherein n is shown as a figure 5. The preparation method of the polyion liquid taking the ionic bond as the framework comprises the following steps:
step a: and (3) performing water and oxygen removal treatment on the 150 ml flask and the 150 ml three-neck flask, wherein the water and oxygen removal treatment comprises the following steps: fully drying a clean 150 ml flask at 90 ℃ for 3 hours, taking out, cooling to room temperature, and introducing nitrogen;
step b: under the protection of nitrogen, adding 2.04 g of 1, 4-dibromobutane and 1.53 g of N-methylimidazole into a flask, continuously stirring at 50 ℃ in an oil bath under heating, taking out a reaction container after 9 hours of reaction, and cooling to obtain 1, 4-dimethylimidazole butane;
step c: cooling 1, 4-dimethyl imidazole butane to room temperature (25 ℃), adding a large amount of acetone, washing for 2 times, breaking the product by using a glass rod, adding a large amount of acetone again, and performing ultrasonic treatment for 15 minutes;
step d: filtering to obtain 1, 4-dimethyl imidazole butane powder, placing the powder in a 150 ml flask, and removing acetone by vacuum rotary evaporation at the temperature of 50 ℃ to obtain pure 1, 4-dimethyl imidazole butane powder;
step e: d, dissolving the 1, 4-dimethyl imidazole butane obtained in the step d in deionized water to obtain 10 ml of 1, 4-dimethyl imidazole butane aqueous solution with the concentration of 0.5mol/L for later use;
step f: putting 2.02 g of 1, 12-dodecanediol and 5.53 g of o-sulfobenzoic anhydride into 80mL of toluene, heating and stirring the mixture in an oil bath at 140 ℃, separating water in the raw materials while refluxing the toluene by using a condensation pipe and a water separator for reaction, and reacting for 12 hours to obtain a DEDBS toluene solution;
step g: after the reaction is finished, cooling the solution to room temperature, taking supernatant, carrying out vacuum spin drying on the supernatant in a water bath at 80 ℃ to obtain DEDBS, dissolving the DEDBS in deionized water, and preparing 10 ml of aqueous solution with the concentration of 0.5 mol/L;
step h: mixing the aqueous solution of 1, 4-dimethyl imidazole butane with the aqueous solution of DEDBS, carrying out vacuum spin-drying in a water bath at the temperature of 80 ℃, and then placing the product in vacuum drying at the temperature of 80 ℃ for 2 days to obtain the novel polyion liquid taking an ionic bond as a framework.
Example 2
The polyion liquid with ionic bonds as the frameworks has a structural formula shown as a formula (3), wherein n is shown as a figure 5. The preparation method of the polyion liquid taking the ionic bond as the framework comprises the following steps:
step a: carrying out water and oxygen removal treatment on a 150 ml flask, wherein the water and oxygen removal treatment comprises the following steps: fully drying a clean 150 ml flask at 90 ℃ for 3 hours, taking out, cooling to room temperature, and introducing nitrogen;
step b: under the protection of nitrogen, adding 5.21 g of 1, 4-dibromobutane and 4.32 g of N-methylimidazole into a flask, heating in an oil bath at 60 ℃, continuously stirring, reacting for 10 hours, taking out the reaction vessel, and cooling to obtain 1, 4-dimethylimidazole butane;
step c: cooling 1, 4-dimethyl imidazole butane to room temperature, adding a large amount of acetone, washing for 2 times, breaking the product by using a glass rod, adding a large amount of acetone again, and performing ultrasonic treatment for 20 minutes;
step d: filtering to obtain 1, 4-dimethyl imidazole butane powder, placing the powder in a 150 ml flask, and removing acetone by vacuum rotary evaporation at the temperature of 50 ℃ to obtain pure 1, 4-dimethyl imidazole butane powder;
step e: d, dissolving the 1, 4-dimethyl imidazole butane obtained in the step d in deionized water to obtain 10 ml of 1, 4-dimethyl imidazole butane aqueous solution with the concentration of 0.5mol/L for later use;
step f: putting 4.53 g of 1, 12-dodecanediol and 11.48 g of o-sulfobenzoic anhydride into 100mL of toluene, heating and stirring the mixture in an oil bath at 140 ℃, separating water in the raw materials while refluxing the toluene by using a condensation pipe and a water separator for reaction, and reacting for 12 hours to obtain a DEDBS toluene solution;
step g: after the reaction is finished, cooling the solution to room temperature, taking supernatant, carrying out vacuum spin drying on the supernatant in a water bath at 80 ℃ to obtain DEDBS, dissolving the DEDBS in deionized water, and preparing 10 ml of aqueous solution with the concentration of 0.5 mol/L;
step h: mixing the aqueous solution of 1, 4-dimethyl imidazole butane with the aqueous solution of DEDBS, carrying out vacuum spin-drying in a water bath at the temperature of 80 ℃, and then placing the product in vacuum drying at the temperature of 80 ℃ for 2 days to obtain the novel polyion liquid taking an ionic bond as a framework.
Example 3
The polyion liquid with ionic bonds as the frameworks has a structural formula shown as a formula (3), wherein n is shown as a figure 5. The preparation method of the polyion liquid taking the ionic bond as the framework comprises the following steps:
step a: carrying out water and oxygen removal treatment on a 150 ml flask, wherein the water and oxygen removal treatment comprises the following steps: fully drying a clean 150 ml flask at 90 ℃ for 3 hours, taking out, cooling to room temperature, and introducing nitrogen;
step b: adding 7.5 g of 1, 4-dibromobutane and 6.0 g of N-methylimidazole into a flask under the protection of nitrogen, carrying out oil bath at 75 ℃ and heating for stirring continuously, taking out a reaction container after 12 hours of reaction, and cooling to obtain 1, 4-dimethylimidazole butane;
step c: cooling 1, 4-dimethyl imidazole butane to room temperature, adding a large amount of acetone, washing for 3 times, breaking the product by using a glass rod, adding a large amount of acetone again, and performing ultrasonic treatment for 30 minutes;
step d: filtering to obtain 1, 4-dimethyl imidazole butane powder, placing the powder in a 150 ml flask, and removing acetone by vacuum rotary evaporation at the temperature of 75 ℃ to obtain pure 1, 4-dimethyl imidazole butane powder;
step e: d, dissolving the 1, 4-dimethyl imidazole butane obtained in the step d in deionized water to obtain 10 ml of 1, 4-dimethyl imidazole butane aqueous solution with the concentration of 0.5mol/L for later use;
step f: putting 2.02 g of 1, 12-dodecanediol and 5.53 g of o-sulfobenzoic anhydride into 50mL of toluene, heating and stirring the mixture in an oil bath at 130 ℃, separating water in the raw materials while refluxing the toluene by using a condensation pipe and a water separator for reaction, and reacting for 12 hours to obtain a DEDBS toluene solution;
step g: after the reaction is finished, cooling the solution to room temperature, taking supernatant, carrying out vacuum spin drying on the supernatant in a water bath at 80 ℃ to obtain DEDBS, dissolving the DEDBS in deionized water, and preparing 10 ml of aqueous solution with the concentration of 0.5 mol/L;
step h: mixing the aqueous solution of 1, 4-dimethyl imidazole butane with the aqueous solution of DEDBS, carrying out vacuum spin-drying in a water bath at the temperature of 80 ℃, and then placing the product in vacuum drying at the temperature of 80 ℃ for 1.5 days to obtain the novel polyion liquid taking an ionic bond as a skeleton.
Example results are shown in the figure
Fig. 1a, 1b and 1c are respectively corresponding to one-dimensional nuclear magnetic hydrogen spectrograms of the novel polyion liquid which is prepared in examples 1, 2 and 3 and takes an ionic bond as a framework. Wherein the single peak at 9.27ppm is the chemical shift of the proton on the methine group attached to two nitrogen atoms on the five-membered ring of imidazole; the multiple peak at 7.75ppm is the chemical shift of the proton near the methyl group on the imidazole ring; the multiple peak at 7.83ppm is the chemical shift of the proton on the imidazole ring near the alkyl chain; the singlet at 4.25ppm is the chemical shift of the proton on the alkyl chain near the imidazole ring; the single peak at 3.87ppm is attributed to the proton of the methyl group on the imidazole; the peak at 1.79ppm is the chemical shift of the proton on the alkane chain of the imidazolebutane; a plurality of absorption peaks located in the range of 7.25ppm to 7.84ppm, which are chemical shifts of protons on a benzene ring; the multiple peak at 4.11ppm is the chemical shift of the proton on the dodecyl chain near the formyl group; the absorption peak located in the range of 1.25ppm to 1.63ppm is the chemical shift of the proton on the dodecyl chain; the broad peak at 5.74ppm is the chemical shift of the active hydrogen on the by-product HBr produced during the synthesis of the polyionic liquid.
FIG. 2 shows a Fourier infrared spectrum of the novel polyion liquid with ionic bonds as the skeleton, which is prepared in example 1. Is located at 3149cm-1、3104cm-1The position is the C-H stretching vibration peak on the imidazole ring in the polyion liquid; is located at 1572cm-1The position is a stretching vibration peak of C ═ C structure on the imidazole ring skeleton; at 2927cm-1、2855cm-1Asymmetric and symmetric stretching vibration peaks of methyl and methylene are formed; at 1460cm-1、1380cm-1The vibration peak of the bending vibration of methylene and methyl is overlapped with the vibration peak of a C ═ C framework on a benzene ring; at 1726cm-1Is the stretching vibration peak of C ═ O; at 1017cm-1～1230cm-1Where is the characteristic peak position of the sulfonic acid group; 2624cm-1The peak is a Br-H bond stretching vibration peak and belongs to a reaction byproduct HBr.
FIG. 3 shows a differential scanning calorimetry thermogram of the novel polyion liquid with ionic bonds as the framework prepared in example 1.
FIG. 4 is a curve corresponding to the thermogravimetric curve of the novel polyionic liquid with ionic bonds as the skeleton prepared in example 1.
FIG. 5 shows the molecular weight and n value of the novel polyion liquid prepared in example 1, example 2 and example 3 and having ionic bonds as the skeleton, which are measured by gel permeation chromatography, and the synthesis of the novel polyion liquid is proved.
Claims (10)
1. A polyion liquid taking an ionic bond as a framework is characterized in that the structural formula is as follows:
wherein n is 150-180.
2. The method for preparing polyion liquid with ionic bonds as frameworks, which is characterized by comprising the following steps: 1, 4-dibromobutane and N-methylimidazole are used as raw materials, and the 1, 4-dimethylimidazole butane is synthesized through quaternization reaction; synthesizing DEDBS by carrying out alcoholysis reaction on 1, 12-dodecanediol and o-sulfobenzoic anhydride; and finally, mixing the aqueous solution of the 1, 4-dimethyl imidazole butane with the aqueous solution of the DEDBS, and spin-drying water to obtain the polyion liquid taking the ionic bond as the framework.
3. The method for preparing polyion liquid with ionic bonds as frameworks, which is characterized by comprising the following steps:
step a: carrying out water removal and oxygen removal treatment on the reaction container;
step b: adding 1, 4-dibromobutane and N-methylimidazole into a reaction vessel under the protection of nitrogen, heating and stirring for reaction to obtain 1, 4-dimethylimidazole butane;
step c: b, cooling the 1, 4-dimethyl imidazole butane obtained in the step b to room temperature, and then adding acetone for washing;
step d: c, rotationally evaporating the 1, 4-dimethyl imidazole butane obtained in the step c in vacuum to remove acetone;
step e: d, dissolving the 1, 4-dimethyl imidazole butane obtained in the step d in deionized water to obtain an aqueous solution of the 1, 4-dimethyl imidazole butane;
step f: putting 1, 12-dodecanediol and o-sulfobenzoic anhydride into toluene, heating in an oil bath, stirring and refluxing to obtain a DEDBS toluene solution;
step g: cooling the solution obtained in the step f, taking the supernatant, performing vacuum spin drying, and dissolving in deionized water to obtain an aqueous solution of DEDBS;
step h: mixing the aqueous solution of 1, 4-dimethyl imidazole butane with the aqueous solution of DEDBS, spin-drying, and vacuum-drying to obtain the polyion liquid with the ionic bond as the skeleton.
4. The method for preparing polyionic liquid with ionic bonds as frameworks according to claim 3, wherein the molar ratio of 1, 4-dibromobutane to N-methylimidazole in the step b is 1: 2.5-3; the reaction temperature in the step b is 50-80 ℃; the reaction time in the step b is 8 to 12 hours.
5. The method for preparing polyion liquid with ionic bond as skeleton in claim 3, wherein in step c, after the 1, 4-dimethyl imidazole butane obtained in step b is cooled to room temperature, acetone is added for washing for 2-3 times, then the reaction product is broken up, and the ultrasonic treatment is carried out in acetone for 15-30 minutes.
6. The method for preparing polyion liquid by taking ionic bonds as frameworks in claim 3, wherein the vacuum rotary evaporation temperature in the step d is 40-60 ℃.
7. The method for preparing polyion liquid with ionic bond as skeleton in claim 3, wherein the concentration of 1, 4-dimethyl imidazole butane solution in step e is 0.5-1 mol/L.
8. The method for preparing polyionic liquid with ionic bonds as frameworks in claim 3, wherein the molar ratio of 1, 12-dodecanediol to o-sulfobenzoic anhydride in step f is 1: 2.5-3; the oil bath temperature in the step f is 120 ℃ and 140 ℃; the reaction time in the step f is 8 to 12 hours.
9. The method for preparing polyion liquid taking ionic bonds as frameworks according to claim 3, wherein the vacuum rotary evaporation temperature in the step g is 70-90 ℃; the concentration of the aqueous solution of the DEDBS in the step h is the same as that of the aqueous solution of the 1, 4-dimethyl imidazole butane.
10. The method for preparing polyion liquid by taking ionic bonds as frameworks according to claim 3, wherein the rotary evaporation temperature in the step h is 70-90 ℃, the vacuum drying temperature is 70-90 ℃, and the time is 1-2 days.
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Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101456844A (en) * | 2007-12-13 | 2009-06-17 | 中国科学院兰州化学物理研究所 | Room temperature ion liquid containing sulfonic acid ester base side chain as well as preparation method and use thereof |
| CN102276642A (en) * | 2010-06-12 | 2011-12-14 | 中国科学院大连化学物理研究所 | Ionic liquid precursor and mesoporous material for supporting ionic liquid precursor, synthesis and application |
| CN102952079A (en) * | 2012-11-27 | 2013-03-06 | 河北工业大学 | Novel imidazolium salt ionic liquid and related luminescent material thereof |
| WO2013181345A3 (en) * | 2012-05-30 | 2014-03-13 | The University Of Toledo | Synthesis of polymeric ionic liquids using a photochemical polymerization process |
| CN105131271A (en) * | 2015-08-12 | 2015-12-09 | 东华大学 | Poly ionic liquid type alkaline indicator suitable for non-polar solvents, and preparation thereof |
| CN105199091A (en) * | 2015-08-12 | 2015-12-30 | 东华大学 | Polyion liquid acid-base indicator suitable for non-polar solvent and preparation method thereof |
| CN106008941A (en) * | 2016-05-19 | 2016-10-12 | 东华大学 | Imidazolyl dyeable modified copolyester for anionic dye and preparation and application of imidazolyl dyeable modified copolyester |
| CN107814932A (en) * | 2017-11-10 | 2018-03-20 | 山东师范大学 | A kind of poly ion liquid organic porous polymer and preparation method and application |
| CN107828032A (en) * | 2017-11-17 | 2018-03-23 | 中南大学 | A kind of hyperbranched starlike poly ion liquid and its preparation method and application |
-
2018
- 2018-05-18 CN CN201810485115.2A patent/CN108676173B/en active Active
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101456844A (en) * | 2007-12-13 | 2009-06-17 | 中国科学院兰州化学物理研究所 | Room temperature ion liquid containing sulfonic acid ester base side chain as well as preparation method and use thereof |
| CN102276642A (en) * | 2010-06-12 | 2011-12-14 | 中国科学院大连化学物理研究所 | Ionic liquid precursor and mesoporous material for supporting ionic liquid precursor, synthesis and application |
| WO2013181345A3 (en) * | 2012-05-30 | 2014-03-13 | The University Of Toledo | Synthesis of polymeric ionic liquids using a photochemical polymerization process |
| CN102952079A (en) * | 2012-11-27 | 2013-03-06 | 河北工业大学 | Novel imidazolium salt ionic liquid and related luminescent material thereof |
| CN105131271A (en) * | 2015-08-12 | 2015-12-09 | 东华大学 | Poly ionic liquid type alkaline indicator suitable for non-polar solvents, and preparation thereof |
| CN105199091A (en) * | 2015-08-12 | 2015-12-30 | 东华大学 | Polyion liquid acid-base indicator suitable for non-polar solvent and preparation method thereof |
| CN106008941A (en) * | 2016-05-19 | 2016-10-12 | 东华大学 | Imidazolyl dyeable modified copolyester for anionic dye and preparation and application of imidazolyl dyeable modified copolyester |
| CN107814932A (en) * | 2017-11-10 | 2018-03-20 | 山东师范大学 | A kind of poly ion liquid organic porous polymer and preparation method and application |
| CN107828032A (en) * | 2017-11-17 | 2018-03-23 | 中南大学 | A kind of hyperbranched starlike poly ion liquid and its preparation method and application |
Non-Patent Citations (1)
| Title |
|---|
| "Linear polymeric ionic liquids as phasetransporters for both cationic and anionic dyes with synergic effects";Hualei Zhao etal;《Polymer Chemistry》;20150813;第5卷(第2期);第7060-7068页 * |
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