CN103346348A - Polymer electrolyte for organic lithium secondary battery and preparation method of polymer electrolyte - Google Patents

Polymer electrolyte for organic lithium secondary battery and preparation method of polymer electrolyte Download PDF

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CN103346348A
CN103346348A CN2013102540902A CN201310254090A CN103346348A CN 103346348 A CN103346348 A CN 103346348A CN 2013102540902 A CN2013102540902 A CN 2013102540902A CN 201310254090 A CN201310254090 A CN 201310254090A CN 103346348 A CN103346348 A CN 103346348A
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electrolyte
polymer
organolithium
secondary cell
organic solvent
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陈军
朱智强
黄苇苇
王利江
王诗文
李�昊
陶占良
梁静
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Nankai University
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries
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Abstract

The invention relates to polymer electrolyte for an organic lithium secondary battery. The polymer electrolyte is characterized by consisting of a polymer matrix and electrolyte, wherein the polymer matrix is a composite polymer consisting of polymethacrylate and/or polyethylene glycol, and the electrolyte is the electrolyte solution containing lithium salt and an organic solvent; and the preparation method comprises the following steps of: mixing the prepared polymer matrix and electrolyte, stirring the mixture until the solid is completely dissolved, and cooling the mixture to the room temperature. The polymer electrolyte and the preparation method have the advantages that the polymer electrolyte has good ion electric conductivity at the room temperature, when the polymer electrolyte is used for preparing the high-performance organic lithium secondary battery, the dissolution of the electrode material can be inhibited; and when the polymer electrolyte is used for forming a quasi-solid battery with a high-specific-capacity organic carbonyl compound, not only can the high capacity characteristic of the organic material be maintained, but also the cycling stability of the battery can be greatly improved, and a good development prospect can be realized for the next generation of high-energy high-power environment-friendly storage battery.

Description

A kind of polymer dielectric for the organolithium secondary cell and preparation method thereof
Technical field
The present invention relates to the preparation of organolithium secondary cell, particularly a kind of polymer dielectric for the organolithium secondary cell and preparation method thereof.
Background technology
The energy of lithium secondary battery Yin Qigao and power density and good cyclicity are used widely in mobile electronic product market at present.Along with continuous advancement in technology, fields such as electric automobile and energy-accumulating power station constantly increase the demand of lithium ion battery, require also to improve constantly.
The tradition positive electrode material of lithium secondary cell is the transition metal oxide of lithium, and theoretical capacity is the principal element of limit battery capacity generally at 140-170 mAh/ g.People require to seek new positive electrode for the pursuit of high power capacity.The organic compound positive electrode is owing to have the theoretical capacity height, cheapness, and reusable edible and height advantage such as can design referring to Y. Liang, Z. Tao, J. Chen, Organic electrode materials for rechargeable lithium batteries Advanced Energy Materials, 2012,2:742 is considered to one of desirable substitution material.But there is serious dissolution problems in this class material in traditional liquid state organic electrolyte, causes that capacity sharply descends in cyclic process, has seriously limited their application.Therefore, need find suitable electrolyte, suppress the dissolving of electrode material, improve the cyclical stability of battery.Not long ago, Honma seminar replaces conventional liquid electrolyte by using room-temperature ion liquid bluk recombination quasi-solid electrolyte, the dissolution problems that suppressed organic electrode material effectively is referring to Y. Hanyu, I. Honma, Rechargeable quasi-solid state lithium battery with organic crystalline cathode Scientific Reports, 2013,2:453; Y. Hanyu, Y. Ganbe, I. Honma, Application of quinonic cathode compounds for quasi-solid lithium batteries, Journal of Power Sources, 2013,221:186.
1973, Englishman Wright has taken the lead in finding to have the conductivity that adds alkali metal salt in certain high molecular weight polymers-polyoxyethylene (PEO), referring to: D. Fenton, J. Parker, P. Wright, Complexes of alkali metal ions with poly (ethylene oxide) Polymer, 1973,14:589.In the near future, people such as Armand have pointed out PEO base polymer electrolyte possibility of its application in solid lithium battery, referring to: M. Armand, J. Chabagno, M. Duclot, Fast Ion Transport in Solids, P. Vashishta, J. Mundy, and G. Shevoy, Editors, Elsevier, New York, 1979, p131.But this system ionic conductivity at room temperature is lower by (about 10 -8S/cm).Organic aprotic solvent is incorporated into the gel polymer electrolyte that forms in the polymer dielectric matrix, has higher ionic conductivity, be used as the electrolyte of multiple electrochemical cell at present.Common polymer electrolyte system mainly contains poly(ethylene oxide), poly--propylene oxide, poly--acrylonitrile, poly--methyl methacrylate, polyvinyl chloride, poly--vinylidene fluoride and poly--several big classes such as biasfluoroethylene-hexafluoropropylene.Wherein, the poly(ethylene oxide) system is because CH wherein 2CH 2The O chain is widely studied for lithium ion good dissolving ability and the good flowability of polymer segment.As a kind of low molecular polyether, polyethylene glycol has confers similar advantages.Simultaneously, polyethylene glycol can increase the adsorption capacity of polymer liquid towards electrolyte, thereby improves the ionic conductivity of polymer dielectric.On the other hand, have ester group on the chain of poly--methacrylate, can form in the molecule rank with polyethylene glycol and mix uniformly.This mixed polymer can a large amount of liquid state organic electrolyte of load, has higher ionic conductivity and chemical stability.Polymer dielectric based on poly--methacrylate and polyethylene glycol is expected to be applied to the organolithium ion battery with in the polymer dielectric.
Summary of the invention
The objective of the invention is at above existing problems, a kind of polymer dielectric for the organolithium secondary cell and preparation method thereof is provided, this polymer dielectric at room temperature has good ionic conductivity, and it can suppress the dissolving of electrode material in the organolithium secondary cell; Utilize this polymer dielectric can prepare high performance organolithium secondary cell.
Technical scheme of the present invention:
A kind of polymer dielectric for the organolithium secondary cell, formed by polymer substrate and electrolyte, described polymer substrate is by the composition polymer of forming of poly--methacrylate and/or polyethylene glycol, electrolyte is the electrolyte solution that contains lithium salts and organic solvent, wherein the chemical structural formula of poly--methacrylate as shown in Equation 1, the chemical structural formula of polyethylene glycol as shown in Equation 2:
Figure 2013102540902100002DEST_PATH_IMAGE001
Formula 1
Figure 269004DEST_PATH_IMAGE002
Formula 2
In the above-mentioned chemical structural formula, n is the integer of 1-100 000.
Described electrolyte is formed by lithium salts and organic solvent mixing, and the concentration of lithium salts in organic solvent is 0.2-1.5 mol/L, and described lithium salts is LiClO 4, LiPF 6, LiBF 4, LiAsF 6, LiCF 3SO 2, LiP (C 6H 4O 2) 3, LiPF 3(C 2F 5) 3, LiB (C 2O 4) 2And LiN (CF 3SO 2) 2The mixture of one or more arbitrary proportions, described organic solvent is ethylene carbonate, propene carbonate, diethyl carbonate, dimethyl carbonate, methyl ethyl carbonate, butylene, carbonic acid first butyl ester and isomer thereof, methyl acetate, methyl propionate, g-butyrolactone, sulfolane, 1,2-dimethoxy-ethane, 1,3-dioxolanes, 4-methyl isophthalic acid, the 3-dioxolanes, propiolic acid, oxolane, the mixture of one or more arbitrary proportions in 2-methyltetrahydrofuran and the dimethyl sulfoxide (DMSO).
A kind of described method for preparing polymer electrolytes for the organolithium secondary cell, step is as follows:
1) methyl acrylate and polyethylene glycol are mixed with ammonium persulfate, under nitrogen protection, in 70 oC stir 5-10 minute complete to polymerization, obtain uniform gelatin polymer matrix;
2) lithium salts and organic solvent are mixed preparation electrolyte, the concentration of lithium salts in organic solvent is 0.2-1.5 mol/L;
3) gelatin polymer matrix is added in this electrolyte, 80 oVigorous stirring exists until no solid under the C, is cooled to 18-25 oBehind the C, make polymer dielectric.
The mass ratio of described methyl acrylate, polyethylene glycol and ammonium persulfate is 1:0.001-10:0.1-1, and the mass ratio of polymer substrate and electrolyte is 1:0.1-50; Described lithium salts is LiClO 4, LiPF 6, LiBF 4, LiAsF 6, LiCF 3SO 2, LiP (C 6H 4O 2) 3, LiPF 3(C 2F 5) 3, LiB (C 2O 4) 2And LiN (CF 3SO 2) 2The mixture of one or more arbitrary proportions; Described organic solvent is ethylene carbonate, propene carbonate, diethyl carbonate, dimethyl carbonate, methyl ethyl carbonate, butylene, carbonic acid first butyl ester and isomer thereof, methyl acetate, methyl propionate, g-butyrolactone, sulfolane, 1,2-dimethoxy-ethane, 1,3-dioxolanes, 4-methyl isophthalic acid, the 3-dioxolanes, propiolic acid, oxolane, the mixture of one or more arbitrary proportions in 2-methyltetrahydrofuran and the dimethyl sulfoxide (DMSO).
A kind of application of described polymer dielectric for the organolithium secondary cell, for the preparation of high performance organolithium secondary cell, this organolithium secondary cell comprises positive pole, negative pole and the described polymer dielectric between positive pole and negative pole, wherein positive electrode is the organic carbonyl compound of high power capacity, negative material is lithium metal or lithium alloy, and wherein the content of lithium is 20-50wt% in the lithium alloy.
Advantage of the present invention is: polyethylene glycol can increase the adsorption capacity of polymer liquid towards electrolyte, thereby improves the ionic conductivity of polymer dielectric; Has ester group on the chain of poly--methacrylate, can form in the molecule rank with polyethylene glycol and mix uniformly, this mixed polymer can a large amount of liquid state organic electrolyte of load, have higher ionic conductivity and chemical stability, when the organic carbonyl compound with high power capacity is positive pole, be assembled into lithium ion battery with this polymer dielectric, not only kept the high advantage of its specific capacity, the dissolution problems that has effectively suppressed simultaneously the organic electrode material of solubility improves the capability retention in the circulation; When selecting cup [4] ketone to be positive pole, battery has the specific discharge capacity height (can reach 420 mAh g -1), the operating voltage height (can reach 2.64 V vs Li/Li +) and advantage such as good cycle (still keep 90% of initial capacity, coulombic efficiency after 100 weeks of circulating〉99 %), be expected to be applied in high energy of future generation, high power, the eco-friendly energy-storage battery.
  
Description of drawings
Fig. 1 is that the ionic conductivity of gel polymer electrolyte is with the lithium salt variation diagram.
Fig. 2 is to be positive active material with cup [4] ketone, and gelatin polymer is that lithium secondary battery of electrolyte is at 0.1mV s -1Under cyclic voltammetry curve.
Fig. 3 is to be positive active material with cup [4] ketone, and gelatin polymer is the first constant current charge-discharge curve of lithium secondary battery of electrolyte under 0.2C.
Fig. 4 is to be positive active material with cup [4] ketone, and gelatin polymer is that the cycle charge discharge capacitance of lithium secondary battery of electrolyte under 0.2C keeps curve.
Fig. 5 is to be positive active material with cup [4] ketone, and gelatin polymer is that the cycle charge discharge capacitance of lithium secondary battery of electrolyte under different multiplying keeps curve.
Fig. 6 is to be positive active material with cup [4] ketone, and gelatin polymer is that the cycle charge discharge capacitance of lithium secondary battery of electrolyte under different temperatures keeps curve.
  
Embodiment
The present invention may be better understood for following examples, but the present invention is not limited to following examples.
Embodiment:
A kind of method for preparing polymer electrolytes for the organolithium ion battery, step is as follows:
1) 0.73 g ammonium persulfate is dissolved in the 4 g polyethylene glycol-600, it is changed in the 7.26 g methyl acrylates, under nitrogen protection, in 70 then oC stir 5 minutes complete to polymerization, obtain uniform gelatin polymer matrix;
2) 0.74 g lithium perchlorate is dissolved in the 10 mL dimethyl sulfoxide (DMSO)s prepares electrolyte;
3) the above-mentioned gelatin polymer matrix of 3.17 g is added in the electrolyte, 80 oVigorous stirring exists until no solid under the C, is cooled to 25 oBehind the C, can obtain uniform gel polymer electrolyte.
Fig. 1 be the ionic conductivity of gel polymer electrolyte with the lithium salt variation diagram, show among the figure: the ionic conductivity of polymer dielectric increases along with the increase of lithium salt, when lithium salt is 0.7 mol/L, reaches maximum 0.57 * 10 -3S cm -1
With the prepared polymer dielectric of organolithium secondary cell that is used for for the preparation of high performance organolithium secondary cell, this organolithium secondary cell comprises positive pole, negative pole and the described polymer dielectric between positive pole and negative pole, wherein positive electrode is cup [4] ketone of high power capacity, and negative pole is lithium metal.
At first prepare positive electrode cup [4] ketone, the synthetic method of cup [4] ketone (target molecule 1) is as follows:
Figure 2013102540902100002DEST_PATH_IMAGE003
1) target molecule 3 is synthetic:
It is in the sodium hydroxide solution of 5w% that 1.37 g para-aminobenzoic acid are dissolved in 10 mL concentration, adds 0.69 g natrium nitrosum then and is cooled to 0 oC is that the hydrochloric acid solution of 6w% slowly is added dropwise to wherein then with 14 mL concentration, obtains solution; Gained solution is joined 50 mL contain in the nitrogen dimethylformamide solution of 1.0 g cup [4] aromatic hydrocarbons, regulate pH to 6-7 by adding sodium acetate, get red suspension-turbid liquid; Place after 2 hours, adding concentration is that the hydrochloric acid adjusting pH of 37w% is 1, obtains a large amount of blush solids; Left standstill 8-12 hour, sediment water and methanol wash with after filtering can obtain crude product 3; Crude product 3 is dissolved in 100 mL 60 oIn the sodium acid carbonate of C (4.2g) solution, add 1 g activated carbon again, after the filtration filtrate be cooled to room temperature, and with concentration be the hydrochloric acid of 37w% to regulate pH be 1, more after filtration, obtain target product 3 after the washing, drying.
2) target molecule 2 is synthetic:
1.76g target product 3 is dissolved in the NaOH solution that 200 mL concentration are 1w%, 90 oUnder the C, add 7.0 g sodium hydrogensulfites reaction 1 hour, obtain white suspension-turbid liquid; Fast cooling to 20 oC obtains white squamous crystal; After the vacuumize, obtain light blue product target molecule 2.
3) target molecule 1 is synthetic:
0.84 g target molecule 2 is dissolved in the 20 mL acetic acid, is heated to 50 oC, slowly add then 16 mL contain 4.0 g iron chloride, concentration be 18w% hydrochloric acid solution, stir after 15 minutes, obtain yellow suspension-turbid liquid; Other gets 2.15 g potassium bichromates and 5.6 mL concentration is that the concentrated sulfuric acid of 98w% joins in the 95 mL water, and above-mentioned yellow suspension-turbid liquid pours into wherein, is heated to 80-90 oC was cooled to 15 after 15 minutes oC, the sediment that obtains are end product target molecule 1.
The preparation of high-performance organolithium secondary cell:
12 mg cup [4] ketone, 6 mg carbon blacks and 2 mg Kynoar are ground to form pulpous state in 80 μ L N-methyl pyrrolidones, evenly are coated on the aluminium foil that diameter is 12 mm, then in-1 MPa air, made electrode slice under 393 K in dry 5 hours.Anodal with this electrode slice work in being full of the glove box of argon gas, polymer dielectric is assembled into lithium secondary battery as electrolyte and barrier film, lithium metal as negative pole.
The lithium secondary battery of preparation carries out constant current charge-discharge under 0.2C(89 mA/g), discharge voltage range is 1.8-3.3 V, the cyclic voltammetry curve of this battery under 0.1mV/ s as shown in Figure 2, show among the figure: battery～2.78V and～3.01V has a pair of reversible redox peak, corresponds respectively to the oxidation of carbonyl and the reduction of enol.
This battery first charge-discharge curve shows among the figure as shown in Figure 3: discharge capacity is 422 mAh g first -1, average discharge volt is 2.64V, coulombic efficiency is 99% first.
The cycle charge discharge capacitance of this battery under 0.2C keeps curve as shown in Figure 4, shows among the figure: through the circulation of 100 weeks, discharge capacity is stabilized in ~ 380 mAh g -1, coulombic efficiency〉and 99%.
The cycle charge discharge capacitance of this battery under different multiplying keeps curve as shown in Figure 5, shows among the figure: at 0.2C, and 0.3C, the discharge capacity under 0.5C and the 1C is respectively 420,377,313 and 225 mAh g -1
The cycle charge discharge capacitance of this battery under different temperatures keeps curve as shown in Figure 6, shows among the figure: at 283 K, and 293 K, the capacity under 303 K after 20 weeks of circulation is respectively 391,410,401 mAh g -1
From the result of embodiment as seen, the gel polymer electrolyte that the present invention proposes can effectively limit the dissolution problems that solubility has machine electrode, improves the cycle performance of battery.When the accurate solid-state organolithium secondary ion battery with the assembling of cup [4] ketone has higher discharge capacity (〉 380 mAh g -1), be higher than conventional inorganic insert material such as LiFePO 4(about 160 mAh g -1) and LiMn 2O 4(about 140 mAh g -1).Optimize by rational electrode/electro pond manufacture craft, such material can show more excellent high rate performance and cyclical stability.So the gel polymer electrolyte that the present invention proposes has a good application prospect in high-performance organolithium secondary cell.

Claims (5)

1. polymer dielectric that is used for the organolithium secondary cell, it is characterized in that: formed by polymer substrate and electrolyte, described polymer substrate is by the composition polymer of forming of poly--methacrylate and/or polyethylene glycol, electrolyte is the electrolyte solution that contains lithium salts and organic solvent, wherein the chemical structural formula of poly--methacrylate as shown in Equation 1, the chemical structural formula of polyethylene glycol as shown in Equation 2:
Figure 2013102540902100001DEST_PATH_IMAGE001
Formula 1
Figure 352413DEST_PATH_IMAGE002
Formula 2
In the above-mentioned chemical structural formula, n is the integer of 1-100 000.
2. according to the described polymer dielectric for the organolithium secondary cell of claim 1, it is characterized in that: described electrolyte is formed by lithium salts and organic solvent mixing, and the concentration of lithium salts in organic solvent is 0.2-1.5 mol/L, and described lithium salts is LiClO 4, LiPF 6, LiBF 4, LiAsF 6, LiCF 3SO 2, LiP (C 6H 4O 2) 3, LiPF 3(C 2F 5) 3, LiB (C 2O 4) 2And LiN (CF 3SO 2) 2The mixture of one or more arbitrary proportions, described organic solvent is ethylene carbonate, propene carbonate, diethyl carbonate, dimethyl carbonate, methyl ethyl carbonate, butylene, carbonic acid first butyl ester and isomer thereof, methyl acetate, methyl propionate, g-butyrolactone, sulfolane, 1,2-dimethoxy-ethane, 1,3-dioxolanes, 4-methyl isophthalic acid, the 3-dioxolanes, propiolic acid, oxolane, the mixture of one or more arbitrary proportions in 2-methyltetrahydrofuran and the dimethyl sulfoxide (DMSO).
3. method for preparing polymer electrolytes that is used for the organolithium secondary cell according to claim 1 is characterized in that step is as follows:
1) methyl acrylate and polyethylene glycol are mixed with ammonium persulfate, under nitrogen protection, in 70 oC stir 5-10 minute complete to polymerization, obtain uniform gelatin polymer matrix;
2) lithium salts and organic solvent are mixed preparation electrolyte, the concentration of lithium salts in organic solvent is 0.2-1.5 mol/L;
3) gelatin polymer matrix is added in this electrolyte, 80 oVigorous stirring exists until no solid under the C, is cooled to 18-25 oBehind the C, make polymer dielectric.
4. according to the described method for preparing polymer electrolytes for the organolithium secondary cell of claim 3, it is characterized in that: the mass ratio of described methyl acrylate, polyethylene glycol and ammonium persulfate is 1:0.001-10:0.1-1, and the mass ratio of polymer substrate and electrolyte is 1:0.1-50; Described lithium salts is LiClO 4, LiPF 6, LiBF 4, LiAsF 6, LiCF 3SO 2, LiP (C 6H 4O 2) 3, LiPF 3(C 2F 5) 3, LiB (C 2O 4) 2And LiN (CF 3SO 2) 2The mixture of one or more arbitrary proportions; Described organic solvent is ethylene carbonate, propene carbonate, diethyl carbonate, dimethyl carbonate, methyl ethyl carbonate, butylene, carbonic acid first butyl ester and isomer thereof, methyl acetate, methyl propionate, g-butyrolactone, sulfolane, 1,2-dimethoxy-ethane, 1,3-dioxolanes, 4-methyl isophthalic acid, the 3-dioxolanes, propiolic acid, oxolane, the mixture of one or more arbitrary proportions in 2-methyltetrahydrofuran and the dimethyl sulfoxide (DMSO).
5. application that is used for the polymer dielectric of organolithium secondary cell according to claim 1, it is characterized in that: for the preparation of high performance organolithium secondary cell, this organolithium secondary cell comprises positive pole, negative pole and the described polymer dielectric between positive pole and negative pole, wherein positive electrode is the organic carbonyl compound of high power capacity, negative material is lithium metal or lithium alloy, and wherein the content of lithium is 20-50wt% in the lithium alloy.
CN2013102540902A 2013-06-25 2013-06-25 Polymer electrolyte for organic lithium secondary battery and preparation method of polymer electrolyte Pending CN103346348A (en)

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Cited By (5)

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CN103553948A (en) * 2013-10-31 2014-02-05 东莞市凯欣电池材料有限公司 Ionic liquid containing ester-based functional group as well as preparation method and application thereof
CN106356194A (en) * 2016-11-24 2017-01-25 东莞理工学院 Polyacrylamide (PAM) solid compound polymer electrolyte and preparation method thereof
CN107317031A (en) * 2017-05-17 2017-11-03 昆明理工大学 Application of the Expired drug aspirin in rechargeable battery
CN110679008A (en) * 2017-06-02 2020-01-10 纳米技术仪器公司 Shape conforming alkali metal-sulfur battery
CN113410066A (en) * 2021-06-09 2021-09-17 华南理工大学 Organic electrode with stable water and oxygen, and preparation method and application thereof

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CN1684298A (en) * 2004-04-12 2005-10-19 黄穗阳 Design and production of colloidal polymer lithium ion cell
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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103553948A (en) * 2013-10-31 2014-02-05 东莞市凯欣电池材料有限公司 Ionic liquid containing ester-based functional group as well as preparation method and application thereof
CN106356194A (en) * 2016-11-24 2017-01-25 东莞理工学院 Polyacrylamide (PAM) solid compound polymer electrolyte and preparation method thereof
CN106356194B (en) * 2016-11-24 2018-08-07 东莞理工学院 A kind of polyacrylamide solid union polymer dielectric and preparation method thereof
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CN110679008A (en) * 2017-06-02 2020-01-10 纳米技术仪器公司 Shape conforming alkali metal-sulfur battery
CN113410066A (en) * 2021-06-09 2021-09-17 华南理工大学 Organic electrode with stable water and oxygen, and preparation method and application thereof
CN113410066B (en) * 2021-06-09 2022-07-26 华南理工大学 Organic electrode with stable water and oxygen, and preparation method and application thereof

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Application publication date: 20131009