CN107978769B - Triazine derivative-based diaphragm for vanadium battery and preparation method thereof - Google Patents
Triazine derivative-based diaphragm for vanadium battery and preparation method thereof Download PDFInfo
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/0644—Poly(1,3,5)triazines
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- H—ELECTRICITY
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- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/18—Regenerative fuel cells, e.g. redox flow batteries or secondary fuel cells
- H01M8/184—Regeneration by electrochemical means
- H01M8/188—Regeneration by electrochemical means by recharging of redox couples containing fluids; Redox flow type batteries
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Abstract
The invention discloses a triazine derivative-based diaphragm for a vanadium battery and a preparation method thereof, which comprises the steps of adding 2, 4-diamino-6-phenyl-1, 3, 5-triazine and 2-chloroethyl vinyl ether into an organic solvent, uniformly mixing, stirring at 30-40 ℃, carrying out reflux reaction for 6-8 hours, carrying out rotary evaporation at 40-50 ℃ to remove the solvent, sequentially washing with ethyl ether and ethyl acetate for 3-5 times, and finally carrying out rotary evaporation at 40-50 ℃ to remove the solvent to obtain a polymeric triazine derivative; then, the polymeric triazine derivative, the polymeric monomer, the perfluoro-n-propyl vinyl ether, the emulsifier and the photoinitiator are mixed and dropped on a glass plate, and the mixture is placed under an ultraviolet lamp with the wavelength of 200-250nm under the atmosphere of nitrogen or inert gas for 45-55 minutes to carry out polymerization reaction, thus obtaining the polymer film. The preparation method is simple and easy to implement, has more excellent mechanical property, ultraviolet aging resistance and chemical stability, higher ionic conductivity and better vanadium resistance, does not use highly toxic raw materials in the preparation process, and is green and environment-friendly.
Description
Technical Field
The invention belongs to the technical field of high polymer materials, relates to a fuel cell component, and particularly relates to a triazine derivative-based diaphragm for a vanadium cell and a preparation method thereof.
Background
With the development of global economy and the increasing population, the available resources on the earth are in short supply and the environmental problem is serious, so that the green new energy technology which can be recycled, is environment-friendly and has high energy conversion efficiency draws wide attention in the industry, and becomes the common pursuit target of the industries and academic circles of various countries. Among them, the all-vanadium redox flow battery, one of the green new energy technologies, has the advantages of long service life, good flexibility, deep discharge, small cross contamination, good stability, etc., and can be used as a clean, efficient and large-scale energy storage device to provide technical support for the continuous use of renewable energy sources such as solar energy, wind energy, tidal energy, etc.
The vanadium battery diaphragm serving as a key material of the vanadium battery can provide H for positive and negative electrolytes+The transmission channel can also prevent the self-discharge effect of the battery caused by the cross contamination of the positive electrolyte and the negative electrolyte. At present, the vanadium battery is mainly usedThe commercial perfluorosulfonic acid type ion exchange membrane mainly comprises a Nafion membrane (U.S. Dupont), which is relatively stable in a strong acid electrolyte and has high proton conductivity, but the penetration phenomenon of vanadium ions is relatively serious, so that the self-discharge effect of the battery is easily caused, the efficiency of the battery is further reduced, and the price is high.
As an improvement, anion exchange membranes appear in the prior art, and the Donan repulsion effect between positively charged groups on the membranes and vanadium ions can effectively prevent the penetration of the vanadium ions, thereby fundamentally preventing the self-discharge effect caused by the mutual cross contamination of electrolytes on both sides of the membranes. However, most of traditional anion exchange membranes are prepared from quaternary ammonium salt polymers, and during the preparation process of the anion exchange membranes, highly toxic substance chloromethyl ether is one of essential raw materials, so that the anion exchange membranes are harmful to human bodies and the environment and are not environment-friendly.
Therefore, there is a need for a more efficient method for preparing a separator for a vanadium battery having excellent mechanical properties, ultraviolet aging resistance, vanadium resistance, and chemical stability, and having high ionic conductivity.
Disclosure of Invention
In order to overcome the defects in the prior art, the invention provides the triazine derivative-based diaphragm for the vanadium battery and the preparation method thereof, the preparation method is simple and easy to implement, the requirement on equipment is not high, the raw materials are easy to obtain, and the cost is low.
In order to achieve the aim, the invention adopts the technical scheme that the preparation method of the triazine derivative-based diaphragm for the vanadium battery comprises the following steps:
1) preparation of polymeric triazine derivatives: adding 2, 4-diamino-6-phenyl-1, 3, 5-triazine and 2-chloroethyl vinyl ether into an organic solvent, uniformly mixing, stirring and refluxing at 30-40 ℃ for 6-8 hours, then carrying out rotary evaporation at 40-50 ℃ to remove the solvent, then washing with ethyl ether and ethyl acetate for 3-5 times respectively in sequence, and finally carrying out rotary evaporation at 40-50 ℃ to remove the solvent;
2) preparation of polymer film: mixing the polymeric triazine derivative prepared in the step 1), a polymeric monomer, perfluoro-n-propyl vinyl ether, an emulsifier and a photoinitiator, dripping the mixture on a glass plate, and placing the glass plate under an ultraviolet lamp with the wavelength of 200-250nm under the atmosphere of nitrogen or inert gas for 45-55 minutes to perform polymerization reaction to obtain a polymer film, namely a triazine derivative-based diaphragm for the vanadium battery;
wherein the mass ratio of the 2, 4-diamino-6-phenyl-1, 3, 5-triazine, the 2-chloroethyl vinyl ether and the organic solvent in the step 1) is 1: (3.5-4): (10-12);
the organic solvent is selected from one or more of dichloromethane, acetonitrile, diethyl ether, ethyl acetate and acetone;
the mass ratio of the polymeric triazine derivative, the polymeric monomer, the perfluoro-n-propyl vinyl ether, the emulsifier and the photoinitiator in the step 2) is (3-4): (3-5): (2-4): (0.05-0.08): (0.1-0.2);
the polymerization type monomer is selected from one or more of acrylonitrile, styrene, α -methyl styrene, methacrylonitrile, sulfonated styrene, octafluorostyrene, methyl methacrylate, ethyl acrylate or methyl sulfonated styrene;
the emulsifier is one or more selected from sodium dodecyl benzene sulfonate, polyoxypropylene polyethylene glycerol ether and nonylphenol polyoxyethylene ether;
the initiator is selected from one or more of benzoin, benzoin dimethyl ether, benzoin ethyl ether, benzoin isopropyl ether and benzoin butyl ether;
the inert gas is selected from one or more of neon, helium and argon.
The triazine derivative-based diaphragm for the vanadium battery is prepared by adopting the preparation method of the triazine derivative-based diaphragm for the vanadium battery;
a vanadium battery employing the triazine derivative-based separator as a separator.
Adopt the produced beneficial effect of above-mentioned technical scheme to lie in:
1) the preparation method based on the triazine derivative diaphragm for the vanadium battery is simple and easy to implement, has low requirements on equipment, easily-obtained raw materials and low price.
2) The triazine derivative-based diaphragm for the vanadium battery, provided by the invention, has a molecular structure containing a triazine derivative structure, and the conjugated structure of the benzene ring and the triazine ring enables the diaphragm to have better ultraviolet aging resistance and alkali resistance.
3) According to the triazine derivative-based diaphragm for the vanadium battery, provided by the invention, more cationic groups are used, the ionic conductivity of the diaphragm is effectively improved under the condition that the mechanical property is not changed, and the Donan rejection effect between more cationic groups and vanadium ions can effectively prevent the penetration of the vanadium ions, so that the self-discharge effect caused by the mutual cross contamination of electrolytes on two sides of the diaphragm is fundamentally prevented, and the vanadium resistance of the diaphragm of the vanadium battery is effectively improved.
4) According to the triazine derivative-based diaphragm for the vanadium battery, provided by the invention, the molecular structure contains ether bonds to form a flexible chain segment, so that the toughness of the diaphragm can be favorably adjusted, the emulsification of an emulsifier is also favorably promoted, the using amount of the emulsifier can be reduced, the cost is saved, and the operation is more convenient.
5) The triazine derivative-based diaphragm for the vanadium battery provided by the invention contains a fluorine chain segment in a molecular structure, and is favorable for improving the mechanical property and the thermal stability of the diaphragm due to the stable carbon-fluorine bond energy, and an ion channel is formed together with a triazine ring, so that the ion conductivity is favorably improved.
6) According to the triazine derivative-based diaphragm for the vanadium battery, provided by the invention, the polymeric triazine derivative can play a role of a cross-linking agent in the whole molecular structure of the diaphragm, so that a molecular chain forms a three-dimensional network structure, and the mechanical property, the chemical stability and the heat resistance of the diaphragm are improved.
Detailed Description
In order to make the technical solutions of the present invention better understood and make the above features, objects, and advantages of the present invention more comprehensible, the present invention is further described with reference to the following examples. The examples are intended to illustrate the invention only and are not intended to limit the scope of the invention.
The raw material used in the following examples of the present invention was obtained from Shanghai spring Xin import & export trade company, Inc.
Example 1
A preparation method of a triazine derivative-based diaphragm for a vanadium battery comprises the following steps:
1) preparation of polymeric triazine derivatives: adding 10g of 2, 4-diamino-6-phenyl-1, 3, 5-triazine and 35g of 2-chloroethyl vinyl ether into 100g of acetonitrile, uniformly mixing, stirring and refluxing at 30 ℃ for 6 hours, then carrying out rotary evaporation at 40 ℃ to remove the solvent, sequentially washing with ethyl ether and ethyl acetate for 3 times respectively, and finally carrying out rotary evaporation at 40 ℃ to remove the solvent;
2) preparation of polymer film: mixing 3g of the polymeric triazine derivative prepared in the step 1), 2g of acrylonitrile, 2g of perfluoro-n-propyl vinyl ether, 0.05g of sodium dodecyl benzene sulfonate and 0.1g of benzoin ethyl ether, dripping the mixture on a glass plate, and placing the glass plate under a 200nm ultraviolet lamp in a nitrogen atmosphere for 45 minutes to perform polymerization reaction to obtain a polymer film;
the triazine derivative-based diaphragm for the vanadium battery is prepared by adopting the preparation method of the triazine derivative-based diaphragm for the vanadium battery;
a vanadium battery employing the triazine derivative-based separator as a separator.
Example 2
A preparation method of a triazine derivative-based diaphragm for a vanadium battery comprises the following steps:
1) preparation of polymeric triazine derivatives: adding 10g of 2, 4-diamino-6-phenyl-1, 3, 5-triazine and 37g of 2-chloroethyl vinyl ether into 110g of diethyl ether, uniformly mixing, stirring and refluxing at 33 ℃ for reaction for 7 hours, then carrying out rotary evaporation at 43 ℃ to remove the solvent, respectively washing with diethyl ether and ethyl acetate for 4 times in sequence, and finally carrying out rotary evaporation at 44 ℃ to remove the solvent;
2) preparation of polymer film: mixing 3.3g of the polymeric triazine derivative prepared in the step 1), 4g of styrene, 3g of perfluoro-n-propyl vinyl ether, 0.06g of polyoxypropylene polyethylene glycerol ether and 0.13g of benzoin dimethyl ether, dripping the mixture on a glass plate, and placing the glass plate under an ultraviolet lamp with the wavelength of 220nm under the argon atmosphere for 48 minutes to perform polymerization reaction to obtain a polymer film;
the triazine derivative-based diaphragm for the vanadium battery is prepared by adopting the preparation method of the triazine derivative-based diaphragm for the vanadium battery;
a vanadium battery employing the triazine derivative-based separator as a separator.
Example 3
A preparation method of a triazine derivative-based diaphragm for a vanadium battery comprises the following steps:
1) preparation of polymeric triazine derivatives: adding 10g of 2, 4-diamino-6-phenyl-1, 3, 5-triazine and 38g of 2-chloroethyl vinyl ether into 113g of acetone, uniformly mixing, stirring and refluxing at 38 ℃ for 8 hours, then carrying out rotary evaporation at 48 ℃ to remove the solvent, sequentially washing with diethyl ether and ethyl acetate for 5 times respectively, and finally carrying out rotary evaporation at 48 ℃ to remove the solvent;
2) preparing a polymer film, namely mixing 3.8g of the polymeric triazine derivative prepared in the step 1), 4.5g of α -methyl styrene, 3.5g of perfluoro-n-propyl vinyl ether, 0.07g of nonylphenol polyoxyethylene ether and 0.18g of benzoin isopropyl ether, dripping the mixture on a glass plate, and placing the glass plate under a 240nm ultraviolet lamp in a neon atmosphere for 55 minutes to perform polymerization reaction to obtain the polymer film;
the triazine derivative-based diaphragm for the vanadium battery is prepared by adopting the preparation method of the triazine derivative-based diaphragm for the vanadium battery;
a vanadium battery employing the triazine derivative-based separator as a separator.
Example 4
A preparation method of a triazine derivative-based diaphragm for a vanadium battery comprises the following steps:
1) preparation of polymeric triazine derivatives: adding 10g of 2, 4-diamino-6-phenyl-1, 3, 5-triazine and 40g of 2-chloroethyl vinyl ether into 120g of ethyl acetate, uniformly mixing, stirring and refluxing at 40 ℃ for 8 hours, then carrying out rotary evaporation at 50 ℃ to remove the solvent, then washing with ethyl ether and ethyl acetate for 5 times respectively, and finally carrying out rotary evaporation at 50 ℃ to remove the solvent;
2) preparation of polymer film: 4g of polymeric triazine derivative prepared in the step 1), 5g of octafluorostyrene, 4g of perfluoro-n-propyl vinyl ether, 0.08g of sodium dodecyl benzene sulfonate and 0.2g of benzoin butyl ether are mixed, dropped on a glass plate, placed under a 250nm ultraviolet lamp in a nitrogen atmosphere for 55 minutes to carry out polymerization reaction, and a polymer film is obtained;
the triazine derivative-based diaphragm for the vanadium battery is prepared by adopting the preparation method of the triazine derivative-based diaphragm for the vanadium battery;
a vanadium battery employing the triazine derivative-based separator as a separator.
Comparative example
Commercially available conventional homogeneous anion exchange membranes are available from Beijing Runfan technology development, Inc.
The samples obtained in the above examples 1 to 4 and comparative example were subjected to the relevant performance tests, the test results are shown in table 1, the test methods are as follows,
(1) and (3) testing tensile strength: testing according to GB/T1040-2006 Plastic tensile Property test method;
(2) ion conductivity: the impedance of the prepared vanadium battery diaphragm is measured on an electrochemical workstation (Zahner IM6 EX) by adopting a two-electrode alternating current impedance method, and the testing frequency is 1 Hz-1 MHz. The conductivity test was performed in a vessel filled with deionized water in order to ensure that the relative humidity of the membrane was 100% and the temperature was controlled at 30 ℃. Before the test at this temperature point, the sample was kept at this temperature for 30min, and the conductivity was calculated according to the following formula:
wherein σ is the conductivity (S cm)-1) L is the distance (cm) between the two electrodes, R is the AC impedance of the sample being measured, and S is the cross-sectional area of the membrane.
(3) Oxidation stability: drying the membrane at 50 deg.C for 6h, rapidly and accurately weighing the mass, and soaking the membrane in 0.1mol L at 40 deg.C-1VO2++3.0mol L-1H2SO4And taking out the solution after 20 hours, washing, drying and measuring the weight retention rate of the diaphragm. The calculation formula is as follows: retention rate (weight of membrane after soaking-weight of membrane before soaking)/weight of membrane before soaking × 100%.
(4) Vanadium ion permeability constant: the test was carried out according to the test method reported in Journal of Powe Sources,2012,217: 309.
TABLE 1 Properties of samples of examples and comparative examples
As can be seen from Table 1, the triazine derivative-based diaphragm for the vanadium battery disclosed by the invention has better mechanical property, oxidation resistance and vanadium ion resistance, and the ion conductivity is higher than that of the traditional anion exchange membrane.
The foregoing is merely a preferred embodiment of the invention and is not intended to limit the invention in any manner; the present invention may be readily implemented by those of ordinary skill in the art as illustrated in the accompanying drawings and described above; however, those skilled in the art should appreciate that they can readily use the disclosed conception and specific embodiments as a basis for designing or modifying other structures for carrying out the same purposes of the present invention; meanwhile, any changes, modifications, and evolutions of the equivalent changes of the above embodiments according to the actual techniques of the present invention are still within the protection scope of the technical solution of the present invention.
Claims (9)
1. A preparation method of a triazine derivative-based diaphragm for a vanadium battery is characterized by comprising the following steps:
1) adding 2, 4-diamino-6-phenyl-1, 3, 5-triazine and 2-chloroethyl vinyl ether into an organic solvent, uniformly mixing, stirring and refluxing at 30-40 ℃ for 6-8 hours, then carrying out rotary evaporation at 40-50 ℃ to remove the solvent, sequentially washing with ethyl ether and ethyl acetate for 3-5 times respectively, and finally carrying out rotary evaporation at 40-50 ℃ to remove the solvent to prepare the polymeric triazine derivative;
2) mixing the polymeric triazine derivative prepared in the step 1), a polymeric monomer, perfluoro-n-propyl vinyl ether, an emulsifier and a photoinitiator, dripping the mixture on a glass plate, and placing the glass plate under an ultraviolet lamp with the wavelength of 200-250nm in the atmosphere of nitrogen or inert gas for 45-55 minutes to perform polymerization reaction to prepare a polymer film, namely a triazine derivative-based diaphragm for the vanadium battery;
the polymeric monomer is selected from one or more of acrylonitrile, styrene, α -methyl styrene, methacrylonitrile, sulfonated styrene, octafluorostyrene, methyl methacrylate, ethyl acrylate or methyl sulfonated styrene.
2. The method for preparing the triazine derivative based separator for the vanadium redox battery according to claim 1, wherein the mass ratio of the 2, 4-diamino-6-phenyl-1, 3, 5-triazine, 2-chloroethyl vinyl ether and the organic solvent in the step 1) is 1: (3.5-4): (10-12).
3. The method for preparing the triazine derivative based diaphragm for the vanadium redox battery according to claim 1, wherein the organic solvent is one or more selected from dichloromethane, acetonitrile, diethyl ether, ethyl acetate and acetone.
4. The method for preparing the triazine derivative-based separator for the vanadium redox battery according to claim 1, wherein the mass ratio of the polymeric triazine derivative, the polymeric monomer, the perfluoro-n-propyl vinyl ether, the emulsifier and the photoinitiator in the step 2) is (3-4): (3-5): (2-4): (0.05-0.08): (0.1-0.2).
5. The method for preparing the triazine derivative based separator for the vanadium redox battery as claimed in claim 1, wherein the emulsifier is one or more selected from sodium dodecyl benzene sulfonate, polyoxypropylene polyethylene glycerol ether and nonylphenol polyoxyethylene ether.
6. The method for preparing the triazine derivative based diaphragm for the vanadium redox battery according to claim 1, wherein the initiator is one or more selected from benzoin, benzoin dimethyl ether, benzoin ethyl ether, benzoin isopropyl ether and benzoin butyl ether.
7. The method for preparing a triazine derivative based diaphragm for a vanadium battery according to claim 1, wherein the inert gas is one or more selected from neon, helium and argon.
8. A triazine derivative-based separator for a vanadium battery, which is prepared by the preparation method according to any one of claims 1 to 7.
9. A vanadium redox battery, characterized in that the triazine derivative based separator for a vanadium redox battery according to claim 8 is used as a polymer electrolyte membrane.
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| JP2010524171A (en) * | 2007-03-30 | 2010-07-15 | ジーエス カルテックス コーポレーション | Raw material composition for high-temperature composite resin separator for fuel cell and high-temperature composite resin separator for fuel cell manufactured using the same |
| CN102741235A (en) * | 2010-02-17 | 2012-10-17 | 日本化成株式会社 | Triazine derivative, and application thereof |
| CN103131094A (en) * | 2011-11-25 | 2013-06-05 | 住友橡胶工业株式会社 | Thermoplastic elastomer composition and medical rubber product |
| CN105914384A (en) * | 2016-06-23 | 2016-08-31 | 先进储能材料国家工程研究中心有限责任公司 | Separator for fuel cell and preparation method of separator |
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| CN1499658A (en) * | 2002-11-01 | 2004-05-26 | 1 | Anti-explosion membrane for lithium ion secondary cell |
| JP2010524171A (en) * | 2007-03-30 | 2010-07-15 | ジーエス カルテックス コーポレーション | Raw material composition for high-temperature composite resin separator for fuel cell and high-temperature composite resin separator for fuel cell manufactured using the same |
| CN102741235A (en) * | 2010-02-17 | 2012-10-17 | 日本化成株式会社 | Triazine derivative, and application thereof |
| CN103131094A (en) * | 2011-11-25 | 2013-06-05 | 住友橡胶工业株式会社 | Thermoplastic elastomer composition and medical rubber product |
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Effective date of registration: 20201106 Address after: Taihu County, Anhui city of Anqing Province Jin Xi Zhen 246400 Patentee after: Taihu County market supervision and Inspection Institute (Taihu County functional membrane Testing Institute) Address before: 410217 Changsha, Changsha City, Hunan Wangcheng economic and Technological Development Zone gold Pioneer Park 4 Building C5 Patentee before: HUNAN CHENLI NEW MATERIAL Co.,Ltd. |