CN103467655A - Preparation method of conductive copolymer film - Google Patents
Preparation method of conductive copolymer film Download PDFInfo
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- CN103467655A CN103467655A CN2013104279739A CN201310427973A CN103467655A CN 103467655 A CN103467655 A CN 103467655A CN 2013104279739 A CN2013104279739 A CN 2013104279739A CN 201310427973 A CN201310427973 A CN 201310427973A CN 103467655 A CN103467655 A CN 103467655A
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Abstract
The invention provides a preparation method of a conductive copolymer film. The preparation method comprises the steps of performing graft copolymerization on conductive vinyl imidazolium-based ionic liquid and unsaturated organic monomers in mole ratio of 1:0.1-1:5 to form a copolymer, and then processing the copolymer by adopting a casting method to form a polymer gel electrolyte film. The prepared polymer gel electrolyte has good film-forming property, high film-forming flexibility, high conductivity (10<-2>-10<-3>s.m<-1>), wide electrochemical window (3-5V) and high thermal stability (200-400 DEG C). The required raw materials are cheap, the operation process is simple, and the product performance is good, and therefore, the preparation method has importation popularization significance in the field of solid electrolyte films.
Description
Technical field
The present invention relates to the copolymerization of vinyl imidazole class ionic liquid and organic monomer and the preparation of gel-form solid polymer electrolyte film thereof.
Background technology
Compared a lot of advantages although polymer dielectric is made to film with aqueous electrolyte, organic solvent ionogen, as to pacify full ﹑ non-volatile etc. without letting out Lou ﹑, but still come with some shortcomings, as low as specific conductivity, electrochemical window is young etc.Because ionic liquid has the various features such as non-volatility, nonflammable, specific conductivity is high, thermal capacity is large, electrochemical window is wide, thereby ionic liquid is incorporated in polymer architecture to the over-all properties that is expected to improve polymer dielectric film.The mode that ionic liquid is combined with polymkeric substance at present mainly contains three kinds: the first is that ionic liquid is direct and polymkeric substance is compound, as patent CN101768349A discloses a kind of ionic-liquid-base polymer, its specific conductivity increases, but electrochemical window, snappiness etc. still await further raising; The second is synthetic polymer in ionic liquid, as patent CN1485357A disclose a kind of in ionic liquid the method for synthesizing polyester, its building-up process is nontoxic, pollution-free to environment, but synthetic polymkeric substance can not directly be used as gel electrolyte because specific conductivity is low; The third is after ion liquid polymerization, with high molecular polymer, to mix again, as patent CN101752090A discloses a kind of preparation method of polyionic liquid base micropore quasi solid state electrolyte, the at first synthetic poly ion liquid of the method, and then prepared poly ion liquid and polyvinylidene difluoride (PVDF) are mixed to get to polymkeric substance.Although the poly ion liquid benchmark solid state electrolyte of gained has improved the stability of battery, electrolytical film-forming properties is still poor.The common shortcoming of above three kinds of modes is that ionic liquid and polymkeric substance directly mix easily generation segregation and cause gel phase inhomogeneous, causes the electrochemical window of gel-form solid polymer electrolyte generally in 2-3 V left and right.Patent " a kind of copolymer gel electrolyte based on RVImX and VAc and preparation method thereof " has overcome this shortcoming, the electrochemical window of the gel-form solid polymer electrolyte prepared wide (3-5 V), Heat stability is good (200-400
oc) and certain electroconductibility (10 arranged
-3~ 10
-5sm
-1), but synthetic copolymer gel electrolyte film-forming properties when masking is not so good, and the film snappiness become is also undesirable, and electroconductibility is also poor, has affected the practical application of this gel-form solid polymer electrolyte.
Summary of the invention
The objective of the invention is to solve the problem that film-forming properties snappiness poor, film is poor and specific conductivity is low of the multipolymer that ionic liquid and polymer monomer copolymerization obtain, by conductive vinyl imidazole class ionic liquid and unsaturated organic monomers copolymerization are obtained to conductive copolymer.And a kind of preparation method of above-mentioned conductive copolymer film is provided, and make the above-mentioned conductive copolymer prepared there is good film-forming property, the film snappiness is good, good conductivity (10
-2~ 10
-3sm
-1) electrochemical window wide (3-5 V), Heat stability is good (200-400
oc) characteristics.
In order to realize the foregoing invention purpose, technical scheme of the present invention is as follows:
A kind of method for preparing the conductive copolymer film, is characterized in that: comprise the steps:
After being mixed, vinyl imidazole class ionic liquid and unsaturated organic monomers be dissolved in solvent orange 2 A (tetracol phenixin, chloroform, iodoform, deuterochloroform, deuterium in iodoform, methylene dichloride, trichloroethane, trieline, zellon, hexanaphthene one or more); add initiator again in this solution; under protection of inert gas; 60-80 ℃ of polyreaction, reaction finishes to obtain by washing, drying the multipolymer of vinyl imidazole class ionic liquid and unsaturated organic monomers.The multipolymer obtained is dissolved in to one or more in solvent B(alcohol, acetonitrile, DMF, DMSO, methane amide, N-Methyl pyrrolidone) in, the method by casting film prepares the gel-form solid polymer electrolyte film.
The structural formula of described vinyl imidazole class ionic liquid is:
.
In described vinyl imidazole class ionic liquid, alkyl (R) is selected from the alkyl that carbonatoms is 0 ~ 8.
X in described vinyl imidazole class ionic liquid
-be selected from Cl
-, Br
-, I
-, BF
4 -, PF
6 -, [(CF
3sO
2)
2n]
-, N (CN)
2 -, CH
3cOO
-, SCN
-, CF3SO
3 -, CH
3cOO
-in a kind of.
Described unsaturated organic monomers is one or more in methacrylic ester, vinylbenzene, NVP, vinylchlorid, vinylidene, ethene, tetrafluoroethylene, carbonic ether.
The amount of substance of described vinyl imidazole class ionic liquid and unsaturated organic monomers is than being 1:0.1 ~ 1:5.
Described initiator is selected from one or more in Diisopropyl azodicarboxylate, 2,2'-Azobis(2,4-dimethylvaleronitrile), azo-bis-iso-dimethyl, azo dicyclohexyl nitrile, acetyl peroxide, benzoyl peroxide, dibenzoyl peroxide, peroxidation two o-methyl-benzene formyls, acetyl peroxide isobutyryl, peroxy dicarbonate diisopropyl acyl, Potassium Persulphate.
The 0.1-1.0 % that the quality of described initiator is ethene imidazoles base ionic liquid and unsaturated organic monomers total mass.
The present invention has prepared the copolymer gel electrolyte of a kind of vinyl imidazole class ionic liquid and unsaturated organic monomers, this gel-form solid polymer electrolyte good film-forming property, and the film snappiness is good, good conductivity (10
-2~ 10
-3sm
-1), and wide electrochemical window (3-5V) is arranged, high thermostability (200-400 ℃).
The accompanying drawing explanation
The preparation flow figure that Fig. 1 is gel-form solid polymer electrolyte film of the present invention.
Embodiment
now, the embodiment of the present invention for the preparation of the conductive copolymer film is described with reference to the drawings.But, the invention is not restricted to this embodiment.
Prepare polymer dielectric film: vinyl imidazole class ionic liquid is dissolved in solvent than for 1:0.1 ~ 1:5 by amount of substance with unsaturated organic monomers; Initiator is joined in this solution, polyreaction finishes to obtain by washing, drying the multipolymer of vinyl imidazole class ionic liquid and unsaturated organic monomers again.The multipolymer obtained is dissolved in to a kind of method by casting film in solvent and prepares the gel-form solid polymer electrolyte film.
Embodiment 1: 12 g bromination N-vinyl-N-ethyl imidazol(e) and 13.71 mL ethene are dissolved in 60 mL chloroforms; Again the mixture of 0.183 g Diisopropyl azodicarboxylate and Potassium Persulphate is joined in this solution, install rapidly prolong, pass into nitrogen and filter after stirring reaction 5 h under 65 ℃ of conditions, obtain gel-form solid polymer electrolyte, with chloroform, wash for several times, 80 ℃ of lower vacuum-dryings are standby; The gel-form solid polymer electrolyte obtained is dissolved in methyl alcohol again, is stirred to evenly, be cast on polyfluortetraethylene plate, drying obtains gel-form solid polymer electrolyte film 1.
Embodiment 2: 12 g bromination N-vinyl-N-ethyl imidazol(e) and 3.26 mL methyl methacrylates and ethene 1.37 mL are dissolved in 60 mL chloroforms; 0.0789 g 2,2'-Azobis(2,4-dimethylvaleronitrile) is joined in this solution again, install rapidly prolong, pass into argon gas and filter after stirring reaction 5 h under 70 ℃ of conditions, obtain gel-form solid polymer electrolyte, wash for several times with chloroform, 80 ℃ of lower vacuum-dryings are standby; The gel-form solid polymer electrolyte obtained is dissolved in methyl alcohol again, is stirred to evenly, be cast on polyfluortetraethylene plate, drying obtains gel-form solid polymer electrolyte film 2.
Embodiment 3: 12 g N-vinyl-N-propyl imidazole tetrafluoride boron and 1.68 mL vinylidenes are dissolved in 60 mL tetracol phenixin; 0.0651 g benzoyl peroxide is joined in this solution again, install rapidly prolong, pass into argon gas and filter after stirring reaction 3 h under 80 ℃ of conditions, obtain gel-form solid polymer electrolyte, wash for several times with tetracol phenixin, 80 ℃ of lower vacuum-dryings are standby; The gel-form solid polymer electrolyte obtained is dissolved in DMF again, is stirred to evenly, be cast on polyfluortetraethylene plate, drying obtains gel-form solid polymer electrolyte film 3.
Embodiment 4: 12 g N-vinyl-N-propyl imidazole tetrafluoride boron and 5.74 mL methyl methacrylates are dissolved in 60 mL trichloroethane; 0.0868 g 2,2'-Azobis(2,4-dimethylvaleronitrile) is joined in this solution again, install rapidly prolong, pass into argon gas and filter after stirring reaction 5 h under 60 ℃ of conditions, obtain gel-form solid polymer electrolyte, wash for several times with trichloroethane, 80 ℃ of lower vacuum-dryings are standby; The gel-form solid polymer electrolyte obtained is dissolved in methyl alcohol and DMSO mixed solvent again, is stirred to evenly, be cast on polyfluortetraethylene plate, drying obtains gel-form solid polymer electrolyte film 4.
Embodiment 5: 12 g N-vinyl-N-propyl imidazole tetrafluoride boron and 6.25 mL vinylbenzene are dissolved in 60 mL chloroforms; 0.0879 g Diisopropyl azodicarboxylate is joined in this solution again, install rapidly prolong, pass into helium and filter after stirring reaction 6 h under 70 ℃ of conditions, obtain gel-form solid polymer electrolyte, wash for several times with chloroform, 80 ℃ of lower vacuum-dryings are standby; The gel-form solid polymer electrolyte obtained is dissolved in DMSO again, is stirred to evenly, be cast on polyfluortetraethylene plate, drying obtains gel-form solid polymer electrolyte film 5.
Embodiment 6: 12 g N-vinyl-N-butyl imidazole phosphorus hexafluoride and 8.69 mL methyl methacrylates are dissolved in 60 mL methylene dichloride; 0.02013 g Potassium Persulphate is joined in this solution again, install rapidly prolong, pass into nitrogen and filter after stirring reaction 3 h under 65 ℃ of conditions, obtain gel-form solid polymer electrolyte, wash for several times with methylene dichloride, 80 ℃ of lower vacuum-dryings are standby; The gel-form solid polymer electrolyte obtained is dissolved in N-Methyl pyrrolidone again, is stirred to evenly, be cast on polyfluortetraethylene plate, drying obtains gel-form solid polymer electrolyte film 6.
Embodiment 7: 12 g N-vinyl-N-butyl imidazole phosphorus hexafluoride and 11.93 mL vinylbenzene are dissolved in 60 mL iodoform; 0.1133 g Diisopropyl azodicarboxylate is joined in this solution again, install rapidly prolong, pass into helium and filter after stirring reaction 5 h under 70 ℃ of conditions, obtain gel-form solid polymer electrolyte, wash for several times with iodoform, 80 ℃ of lower vacuum-dryings are standby; The gel-form solid polymer electrolyte obtained is dissolved in acetonitrile again, is stirred to evenly, be cast on polyfluortetraethylene plate, drying obtains gel-form solid polymer electrolyte film 7.
Embodiment 8: 12 g N-vinyl-N-octyl group imidazoles phosphorus hexafluoride and 11.15 mL NVPs are dissolved in the mixed solvent of 60 mL chloroforms and iodoform; 0.1168 g 2,2'-Azobis(2,4-dimethylvaleronitrile) is joined in this solution again, install rapidly prolong, pass into argon gas and filter after stirring reaction 6 h under 80 ℃ of conditions, obtain gel-form solid polymer electrolyte, wash for several times with chloroform, 80 ℃ of lower vacuum-dryings are standby; The gel-form solid polymer electrolyte obtained is dissolved in DMF again, is stirred to evenly, be cast on polyfluortetraethylene plate, drying obtains gel-form solid polymer electrolyte film 8.
The character of the gel-form solid polymer electrolyte film obtained is as follows:
| Embodiment | Film-forming properties | The film flexibility | Specific conductivity (sm -1） | Electrochemical window (V) | Thermostability (℃) |
| 1 | Well | Well | 1.0*10 -3 | 5.0 | 329 |
| 2 | Well | Well | 6.2*10 -3 | 4.2 | 280 |
| 3 | Well | Well | 2.1*10 -3 | 4.3 | 295 |
| 4 | Well | Well | 5.5*10 -2 | 4.8 | 317 |
| 5 | Well | Well | 7.9*10 -2 | 4.6 | 307 |
| 6 | Well | Well | 8.7*10 -3 | 4.9 | 310 |
| 7 | Well | Well | 2.3*10 -2 | 5.0 | 320 |
| 8 | Well | Well | 1.5*10 -3 | 4.5 | 295 |
Claims (3)
1. a method for preparing the conductive copolymer film, is characterized in that comprising the steps:
To after vinyl imidazole class ionic liquid and unsaturated organic monomers mixing, be dissolved in solvent orange 2 A, add initiator again in this solution, under protection of inert gas, 60-80 ℃ of polyreaction, reaction finishes to obtain by washing, drying the multipolymer of vinyl imidazole class ionic liquid and unsaturated organic monomers, multipolymer is dissolved in solvent B, and the method by casting film prepares the gel-form solid polymer electrolyte film;
The structural formula of described vinyl imidazole class ionic liquid is:
;
In described vinyl imidazole class ionic liquid, alkyl R is selected from the alkyl that carbonatoms is 0 ~ 8;
X in described vinyl imidazole class ionic liquid
-be selected from Cl
-, Br
-, I
-, BF
4 -, PF
6 -, [(CF
3sO
2)
2n]
-, N (CN)
2 -, CH
3cOO
-, SCN
-, CF3SO
3 -, CH
3cOO
-in a kind of;
Described unsaturated organic monomers is one or more in methacrylic ester, vinylbenzene, NVP, vinylchlorid, vinylidene, ethene, tetrafluoroethylene, carbonic ether;
The amount of substance of described vinyl imidazole class ionic liquid and unsaturated organic monomers is than being 1:0.1 ~ 1:5;
Described solvent orange 2 A is tetracol phenixin, chloroform, iodoform, deuterochloroform, deuterium for one or more in iodoform, methylene dichloride, trichloroethane, trieline, zellon, hexanaphthene;
Described solvent B is one or more in alcohol, acetonitrile, DMF, DMSO, methane amide, N-Methyl pyrrolidone.
2. the described method for preparing the conductive copolymer film as claimed in claim 1, it is characterized in that: initiator is selected from one or more in Diisopropyl azodicarboxylate, 2,2'-Azobis(2,4-dimethylvaleronitrile), azo-bis-iso-dimethyl, azo dicyclohexyl nitrile, acetyl peroxide, benzoyl peroxide, dibenzoyl peroxide, peroxidation two o-methyl-benzene formyls, acetyl peroxide isobutyryl, peroxy dicarbonate diisopropyl acyl, Potassium Persulphate.
3. the described method for preparing the conductive copolymer film as claimed in claim 1, is characterized in that: the 0.1-1.0 % that the quality of described initiator is ethene imidazoles base ionic liquid and unsaturated organic monomers total mass.
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104861183A (en) * | 2015-05-13 | 2015-08-26 | 杭州师范大学 | Nanometer tectonic polyvinylidene fluoride composite material and preparation method thereof |
| CN105037609A (en) * | 2015-09-13 | 2015-11-11 | 长春工业大学 | Preparing method for methyl methacrylate polymer |
| CN105949367A (en) * | 2016-05-11 | 2016-09-21 | 常州大学 | Polymer electrolyte film adopting hydrophilic/hydrophobic interpenetrating network structure and preparation method of film |
| CN111499778A (en) * | 2020-04-29 | 2020-08-07 | 中国科学技术大学 | Antibacterial polyolefin material and preparation method and application thereof |
| CN111987361A (en) * | 2020-08-17 | 2020-11-24 | 仲恺农业工程学院 | Imidazole polyion liquid electrolyte and preparation method and application thereof |
| CN112987425A (en) * | 2021-03-15 | 2021-06-18 | 中科院过程工程研究所南京绿色制造产业创新研究院 | Electrochromic device |
| CN113528041A (en) * | 2021-07-29 | 2021-10-22 | 江苏斯迪克新材料科技股份有限公司 | Flame-retardant antistatic protective film and preparation method thereof |
| CN113651913A (en) * | 2021-09-10 | 2021-11-16 | 浙江巨化股份有限公司氟聚厂 | Preparation method of high-strength polytetrafluoroethylene resin |
| CN114400374A (en) * | 2021-12-21 | 2022-04-26 | 中国科学院苏州纳米技术与纳米仿生研究所 | Polymer electrolyte and preparation method and application thereof |
| CN115304710A (en) * | 2022-08-30 | 2022-11-08 | 辽宁大学 | Ionic liquid-based copolymer gel electrolyte and preparation method thereof |
Citations (2)
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|---|---|---|---|---|
| CN101844042A (en) * | 2010-05-21 | 2010-09-29 | 厦门大学 | Preparation method of anion-exchange membranes based on ionic liquid |
| CN102382321A (en) * | 2011-08-31 | 2012-03-21 | 天津大学 | Double-solvent preparation method of ion conductive polymer films |
-
2013
- 2013-09-21 CN CN2013104279739A patent/CN103467655A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101844042A (en) * | 2010-05-21 | 2010-09-29 | 厦门大学 | Preparation method of anion-exchange membranes based on ionic liquid |
| CN102382321A (en) * | 2011-08-31 | 2012-03-21 | 天津大学 | Double-solvent preparation method of ion conductive polymer films |
Cited By (14)
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|---|---|---|---|---|
| CN104861183A (en) * | 2015-05-13 | 2015-08-26 | 杭州师范大学 | Nanometer tectonic polyvinylidene fluoride composite material and preparation method thereof |
| CN105037609A (en) * | 2015-09-13 | 2015-11-11 | 长春工业大学 | Preparing method for methyl methacrylate polymer |
| CN105949367A (en) * | 2016-05-11 | 2016-09-21 | 常州大学 | Polymer electrolyte film adopting hydrophilic/hydrophobic interpenetrating network structure and preparation method of film |
| CN105949367B (en) * | 2016-05-11 | 2019-03-22 | 常州大学 | A kind of hydrophilic/hydrophobic inierpeneirating network structure polymer dielectric film and preparation method thereof |
| CN111499778B (en) * | 2020-04-29 | 2021-10-01 | 中国科学技术大学 | Antibacterial polyolefin material and preparation method and application thereof |
| CN111499778A (en) * | 2020-04-29 | 2020-08-07 | 中国科学技术大学 | Antibacterial polyolefin material and preparation method and application thereof |
| CN111987361A (en) * | 2020-08-17 | 2020-11-24 | 仲恺农业工程学院 | Imidazole polyion liquid electrolyte and preparation method and application thereof |
| CN112987425A (en) * | 2021-03-15 | 2021-06-18 | 中科院过程工程研究所南京绿色制造产业创新研究院 | Electrochromic device |
| CN112987425B (en) * | 2021-03-15 | 2023-02-21 | 中科南京绿色制造产业创新研究院 | Electrochromic device |
| CN113528041A (en) * | 2021-07-29 | 2021-10-22 | 江苏斯迪克新材料科技股份有限公司 | Flame-retardant antistatic protective film and preparation method thereof |
| CN113651913A (en) * | 2021-09-10 | 2021-11-16 | 浙江巨化股份有限公司氟聚厂 | Preparation method of high-strength polytetrafluoroethylene resin |
| CN114400374A (en) * | 2021-12-21 | 2022-04-26 | 中国科学院苏州纳米技术与纳米仿生研究所 | Polymer electrolyte and preparation method and application thereof |
| CN114400374B (en) * | 2021-12-21 | 2023-08-18 | 中国科学院苏州纳米技术与纳米仿生研究所 | Polymer electrolyte, all-solid-state high-voltage lithium metal battery and preparation method thereof |
| CN115304710A (en) * | 2022-08-30 | 2022-11-08 | 辽宁大学 | Ionic liquid-based copolymer gel electrolyte and preparation method thereof |
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Application publication date: 20131225 |