CN1089782C - Method for preparing positive electrode material of lithium secondary cell - Google Patents

Method for preparing positive electrode material of lithium secondary cell Download PDF

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CN1089782C
CN1089782C CN97118189A CN97118189A CN1089782C CN 1089782 C CN1089782 C CN 1089782C CN 97118189 A CN97118189 A CN 97118189A CN 97118189 A CN97118189 A CN 97118189A CN 1089782 C CN1089782 C CN 1089782C
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organic
polyaniline
compound
dimercapto
mol ratio
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CN1217357A (en
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于雷
王献红
李季
景遐斌
王佛松
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Changchun Institute of Applied Chemistry of CAS
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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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    • Y02E60/10—Energy storage using batteries

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Abstract

The present invention belongs to a method for preparing an anode material of secondary lithium batteries. The method comprises the following steps: mixed liquor of polyaniline, an organic disulfide and an organic sulfhydryl compound is prepared in N-methyl pyrrolidone and is painted with brushes or cast on the fluid surfaces of copper, aluminum, platinum or stainless steel; after the surfaces are dried, the anodes of the secondary lithium batteries are prepared. The use of the organic single sulfhydryl compound as a blocking agent can effectively control the increase of the molecular weight in the process of charging the batteries so that the polyaniline and the organic disulfide are nicely compatible to each other in a charge process and a discharge process, the electrocatalysis of the polyaniline and the electrical activity of the disulfide can be fully exerted, and the active anode material with high specific energy and cycle performance can be obtained.

Description

The preparation method of anode material for lithium secondary battery
The invention belongs to the preparation method of anode material for lithium secondary battery.
Along with the great attention of people to energy issue of world, society is to high specific energy, the demand of the chemical power source that discharges and recharges capable of circulation is more and more urgent, especially the high speed development of automotive industry, the chemical power source that can be used for electromobile has been played huge pushing effect, 1989, people such as the S.J.Visco of the U.S. electrochemistry can will " A Novel Class of Organosulfur Electrodefor Energy Strorage " (J.Electrochem.Soc.136 (661) 1989) and Novel SolidRedox Polymerization Electrode " reported the positive electrode material of usefulness organic disulfide in the articles such as (J.Electrochem.Soc.138 (1891) 1991) as lithium cell, obtained the great attention of various countries scholar and industry member.Organic disulfide have high specific energy (＞900wh/kg), scope that can be in normal temperature～150 ℃ is used.The lithium solid electrolyte dimercaptothiodiazole battery of laboratory assembling reaches 140Wh/kg at 100 ℃ of specific energies.
Although organic disulfide has high energy storage density, its redox reaction at normal temperatures is very slow, and this becomes the important factor that hinders this material use.Nineteen ninety-five Japan people such as N.Oyama at nature " Dimercapton-Polyaniline CompositeElectrodes for Lithium Batteries with High Energy Density " (Nature, 373 (598) 1995) etc. reported compound in the article as positive electrode material with polyaniline and organic disulfide, make the redox reaction speed and the reversibility of organic disulfide obtain significant raising, specific storage reaches 185Ah/kg, at room temperature with 0.1mA/cm 2Current density can cycle charge-discharge 80 circles and capacity does not have noticeable change.Polyaniline has played electrochemical katalysis therein, but and polyaniline itself also as one of positive active material of energy storage.Chinese patent 96118933.9 uses polyaniline derivative compound as electrochemical catalyst and organic disulfide, has obtained better electrochemical catalysis effect.
The preparation method who the purpose of this invention is to provide a kind of anode material for lithium secondary battery, in the mixture of the organic dimercapto compound of polyaniline, add the molecular weight of organic single sulfhydryl compound, obtain positive electrode material with higher specific storage and better cycle ability as end-capping reagent control process of charging disulphide polymkeric substance.
Oxidation and the reduction reaction of organic dimercapto compound positive electrode material in battery charge and discharge process conciliate collecting process with respect to its polymerization, just strong generation and the breaking-down process of S-S.When using the organic dimercapto compound of polyaniline composite positive pole, the high molecular weight polymers that the dimercapto compound forms in process of charging will be separated from mixture, thereby limited the electron transport between disulphide and the polyaniline, make that electrode discharge after charging is difficult, influenced the performance of cycle charge-discharge.Add single sulfhydryl compound in the anode composite active material, play the effect of end-capping reagent, the polymerisate of process of charging is controlled to be the lower oligopolymer of molecular weight, thereby has overcome the problems referred to above, its reaction process is as follows:
Figure C9711818900062
The present invention adds organic single sulfhydryl compound as end-capping reagent in the mixture of polyaniline and organic dimercapto compound, the preparation lithium secondary battery positive active material, and each component composition and preparation method are as follows: 1) polyaniline
Figure C9711818900071
Wherein, y=0～1,
Ri=-H ,-Cl ,-C nH 2n+1Or-OC nH 2n+1(n=1～18) 2) organic dimercapto compound:
(1) 2,5-dimercapto-1,3,4 thiadiazoles
(2) trithiocyanuric acid
Figure C9711818900073
(3) 2-sulfydryl ethyl-sulfide HSCH 2CH 2SCH 2CH 2SH
(4) 1,5-naphthyl disulfide phenol
(5) 1,4-two thiopurine methyltransferase benzene
Figure C9711818900075
(6) 1, dithio-hydroquinone 3) organic single sulfhydryl compound:
(1) 2-mercaptobenzothiazole
Figure C9711818900082
(2) bismuthiol II
Figure C9711818900083
(3) 2-sulfydryl-5-methyl isophthalic acid, 3, the 4-thiadiazoles
(4) thiophenol
(5) N, N-dimethyl thiuram sodium salt
Figure C9711818900086
(6) 2 mercapto ethanol HOCH 3CH 2SH
Respectively get above-mentioned six kinds of organic dimercapto compounds and six kinds of organic single sulfhydryl compounds wherein a kind of, after polyaniline mixes, under induction stirring, be dissolved in N-Methyl pyrrolidone or the dimethyl formamide, wherein the mol ratio of aniline unit and mercapto groups is 1/1～1.6, the mol ratio of organic dimercapto compound and organic single sulfhydryl compound is 0.5/1～24/1, continue to stir 4～12 hours, subsequently, mixture is used ultrasonication 2～12 hours, again mixture was handled 1～6 hour with colloidal mill or in the vibrator that adds granulated glass sphere, the mixture of gained evenly is applied to collection liquid surface with the method for brushing or cast, collector comprises copper, aluminium, platinum or stainless steel, in air, volatilize whole solvents, dry in a vacuum 24～48 hours again, the 2～20mg/cm that obtains 2Positive pole.
The anode material for lithium secondary battery of the present invention's preparation has good redox reversible and high energy storage density, method is simple, can under the situation that does not need complex industrial equipment and operational means, prepare the anode composite of polyaniline, organic dimercapto compound and organic single sulfhydryl compound; In polyaniline and organic dimercapto compound complex, add of the growth of organic single sulfhydryl compound as molecular weight in the end-capping reagent control process of charging, avoid causing being separated between polyaniline and the disulphide, make the compound of the two near molecular level because of the disulphide molecular weight increases two; Can obtain, cycle performance better positive electrode material higher than independent use dimercapto compound and the compound specific storage of polyaniline; Methods such as brushing, casting can be used, and, the positive electrode material of all thickness can be obtained by selecting different concentration.
Embodiment provided by the invention is as follows:
Embodiment 1:
Polyaniline 0.341g, 2,5-dimercaptothiodiazole 0.225g and 2-mercaptobenzothiazole 0.500g, wherein the mol ratio of polyaniline unit and mercapto groups is 1/1.6,2, the mol ratio of 5-dimercaptothiodiazole and 2-mercaptobenzothiazole is 1/2, under condition of stirring, add successively in the 15mlN-methyl-2-pyrrolidone, make mixing solutions, stirred 12 hours.Said mixture is passed through supersound process 4 hours again, used milling treatment of colloid again 1 hour, be applied to the platinum collection liquid surface, in air, use infrared oven dry, and vacuum-drying 48h, anode composite obtained.With lithium is counter electrode and reference electrode, uses PC/1M LiClO 4Electrolytic solution is assembled into battery under argon atmospher.This battery is with 0.1mA/cm 2Current density be charged to 4.2V, discharge into 2.0V with same current density again.Loading capacity is 68Ah/kg first, reduces to 41Ah/kg after ten circulations.
Embodiment 2:
Polyaniline 0.228g, 2,5-dimercaptothiodiazole 0.225g and 2-sulfydryl-5-methyl isophthalic acid, 3,4-thiadiazoles 0.132g, wherein the mol ratio of polyaniline unit and mercapto groups is 1/1.6,2,5-dimercaptothiodiazole and 2-sulfydryl-5-methyl isophthalic acid, 3, the mol ratio of 4-thiadiazoles is 3/2, adds successively under condition of stirring in the 10ml N-Methyl pyrrolidone, make mixing solutions, treating processes, battery assembling and to discharge and recharge experiment identical with embodiment 1, loading capacity is 72Ah/kg first, 45Ah/kg is reduced in ten circulations afterwards.
Embodiment 3:
Polyaniline 0.180g, 2,5-dimercaptothiodiazole 0.225g and 2-mercaptobenzothiazole 0.028g, wherein the mol ratio of polyaniline unit and mercapto groups is 1/1.6,2, the mol ratio of 5-dimercaptothiodiazole and 2-mercaptobenzothiazole is 9/1, adds successively under condition of stirring in the 8ml N-Methyl pyrrolidone, make mixing solutions, treating processes, battery assembling and to discharge and recharge experiment identical with embodiment 1, loading capacity is 70Ah/kg first, 27Ah/kg is reduced in ten circulations afterwards.
Embodiment 4:
Aniline 0.228g, 2,5-dimercaptothiodiazole 0.225g and 2-mercaptobenzothiazole 0.170g, wherein the mol ratio of polyaniline unit and mercapto groups is 1/1.6,2, the mol ratio of 5-dimercaptothiodiazole and 2-mercaptobenzothiazole is 3/2, adds successively under condition of stirring in the 10ml dimethyl formamide, make mixing solutions, treating processes, battery assembling and to discharge and recharge experiment identical with embodiment 1, loading capacity is 70Ah/kg first, 47Ah/kg is reduced in ten circulations afterwards.
Embodiment 5:
Poly-ortho position monomethylaniline 0.263g, 2,5-dimercaptothiodiazole 0.225g and 2-mercaptobenzothiazole 0.170g, the mol ratio of wherein poly-monomethylaniline unit, ortho position and mercapto groups is 1/1.6,2, the mol ratio of 5-dimercaptothiodiazole and 2-mercaptobenzothiazole is 3/2, under condition of stirring, add in the 10ml N-Methyl pyrrolidone successively, make mixing solutions, it is identical with embodiment 1 that experiment is assembled and discharged and recharged to treating processes, battery, loading capacity is 63Ah/kg first, reduces to 34Ah/kg after ten circulations.
Embodiment 6:
N-methyl polyaniline (the nitrogen substitute proportion is 36%) 0.240g, 2,5-dimercaptothiodiazole 0.225g and bismuthiol II0.230g, wherein the mol ratio of N-methyl polyaniline unit and mercapto groups is 1/1.6,2, the mol ratio of 5-dimercaptothiodiazole and bismuthiol II is 3/2, under condition of stirring, add in the 10ml N-Methyl pyrrolidone successively, make mixing solutions, it is identical with embodiment 1 that experiment is assembled and discharged and recharged to treating processes, battery, loading capacity is 75Ah/kg first, reduces to 39Ah/kg after ten circulations.
Embodiment 7:
Polyaniline 0.228g, to diphenyl disulfide phenol 0.218g and thiophenol 0.110g, wherein the mol ratio of polyaniline unit and mercapto groups is 1/1.6, mol ratio to diphenyl disulfide phenol and thiophenol is 3/2, under condition of stirring, add in the 10mlN-methyl-2-pyrrolidone successively, make mixing solutions, treating processes, battery assembling and to discharge and recharge experiment identical with embodiment 1, loading capacity is 74Ah/kg first, 30Ah/kg is reduced in ten circulations afterwards.
Embodiment 8:
Polyaniline 0.228g, to two thiopurine methyltransferase benzene 0.257g and N, N-dimethyl thiuram sodium salt 0.143g, wherein the mol ratio of polyaniline unit and mercapto groups is 1/1.6, to two thiopurine methyltransferase benzene and N, the mol ratio of N-dimethyl thiuram sodium salt is 3/2, adds successively under condition of stirring in the 10ml N-Methyl pyrrolidone, make mixing solutions, treating processes, battery assembling and to discharge and recharge experiment identical with embodiment 1, loading capacity is 57Ah/kg first, 22Ah/kg is reduced in ten circulations afterwards.
Embodiment 9:
Polyaniline 0.228g, 1,5-naphthyl disulfide phenol 0.290g and thiophenol 0.110g, wherein the mol ratio of polyaniline unit and mercapto groups is 1/1.6,1, the mol ratio of 5-naphthyl disulfide phenol and thiophenol is 3/2, adds successively under condition of stirring in the 10ml N-Methyl pyrrolidone, make mixing solutions, treating processes, battery assembling and to discharge and recharge experiment identical with embodiment 1, loading capacity is 65Ah/kg first, 26Ah/kg is reduced in ten circulations afterwards.
Embodiment 10:
Polyaniline 0.228g, 2-sulfydryl ethyl-sulfide 0.230g and 2 mercapto ethanol 0.078g, wherein the mol ratio of polyaniline unit and mercapto groups is 1/1.6, the mol ratio of 2-sulfydryl ethyl-sulfide and 2 mercapto ethanol is 3/2, under condition of stirring, add in the 10ml N-Methyl pyrrolidone successively, make mixing solutions, treating processes, battery assembling and to discharge and recharge experiment identical with embodiment 1, loading capacity is 48Ah/kg first, 20Ah/kg is reduced in ten circulations afterwards.
Embodiment 11:
Polyaniline 0.342g, trithiocyanuric acid 0.134g and 2-sulfydryl-5-methyl isophthalic acid, 3,4-thiadiazoles 0.200g, wherein the mol ratio of polyaniline unit and mercapto groups is 1/1, trithiocyanuric acid and 2-sulfydryl-5-methyl isophthalic acid, 3, the mol ratio of 4-thiadiazoles is 1/2, under condition of stirring, add in the 15ml N-Methyl pyrrolidone successively, make mixing solutions, treating processes, battery assembling and to discharge and recharge experiment identical with embodiment 1, loading capacity is 82Ah/kg first, 43Ah/kg is reduced in ten circulations afterwards.

Claims (1)

1, a kind of preparation method of anode material for lithium secondary battery, it is characterized in that adding in the mixture of polyaniline and organic dimercapto compound organic single sulfhydryl compound as end-capping reagent, the preparation lithium secondary battery positive active material, the each component composing method is as follows: 1) polyaniline Wherein, y=0～1,
Ri=-H ,-Cl ,-C nH 2n+1Or-OC nH 2n+1N=1～182) organic dimercapto compound:
(1) 2,5-dimercapto-1,3,4 thiadiazoles
(2) trithiocyanuric acid
Figure C9711818900023
(3) 2-sulfydryl ethyl-sulfide HSCH 2CH 2SCH 2CH 2SH
(4) 1,5-naphthyl disulfide phenol
Figure C9711818900024
(5) 1,4-two thiopurine methyltransferase benzene
(6) 1, dithio-hydroquinone
Figure C9711818900031
3) organic single sulfhydryl compound:
(1) 2-mercaptobenzothiazole
Figure C9711818900032
(2) bismuthiol II
Figure C9711818900033
(3) 2-sulfydryl-5-methyl isophthalic acid, 3, the 4-thiadiazoles
Figure C9711818900034
(4) thiophenol
(5) N, N-dimethyl thiuram sodium salt
(6) 2 mercapto ethanol HOCH 3CH 2SH
Respectively get above-mentioned six kinds of organic dimercapto compounds and six kinds of organic single sulfhydryl compounds wherein a kind of, after polyaniline mixes, under induction stirring, be dissolved in N-Methyl pyrrolidone or the dimethyl formamide, wherein the mol ratio of aniline unit and mercapto groups is 1/1～1.6, the mol ratio of organic dimercapto compound and organic single sulfhydryl compound is 0.5/1～24/1, continue to stir 4～12 hours, subsequently, mixture is used ultrasonication 2～12 hours, again mixture was handled 1～6 hour with colloidal mill or in the vibrator that adds granulated glass sphere, the mixture of gained evenly is applied to collection liquid surface with the method for brushing or cast, collector comprises copper, aluminium, platinum or stainless steel, in air, volatilize whole solvents, dry in a vacuum 24～48 hours again, the 2～20mg/cm that obtains 2Positive pole.
CN97118189A 1997-11-11 1997-11-11 Method for preparing positive electrode material of lithium secondary cell Expired - Fee Related CN1089782C (en)

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CN1310368C (en) * 2004-06-24 2007-04-11 张燕珊 Lithium ion cell slurry mixing method and special purpose mixing equipment therefor
CN100411230C (en) * 2006-06-08 2008-08-13 上海交通大学 Application of organic sulfide in positive electrode material of secondary Mg battery
CN100349961C (en) * 2006-06-22 2007-11-21 广州大学 Polydianilbisulfide and its preparation method
CN100509884C (en) * 2007-08-16 2009-07-08 聊城大学 Copolymerization type intrinsic conductive polymer and method for preparing same
CN102148360A (en) * 2010-02-10 2011-08-10 中航锂电（洛阳）有限公司 Slurry mixing process for lithium ion power batteries
CN109575288B (en) * 2018-10-23 2020-09-11 北京航空航天大学 Polymeric sulfur positive electrode material and lithium-sulfur secondary battery prepared from same
CN110759388B (en) * 2019-10-10 2022-01-04 江苏理工学院 Organic molecule modified lithium-rich material and preparation method thereof

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JPH03147277A (en) * 1989-11-01 1991-06-24 Sanyo Electric Co Ltd Nonaqueous electrolyte secondary battery
JPH03182057A (en) * 1989-12-08 1991-08-08 Sanyo Electric Co Ltd Manufacture of secondary battery with non-aqueous electrolytic solution
JPH03182059A (en) * 1989-12-11 1991-08-08 Sanyo Electric Co Ltd Secondary battery with non-aqueous electrolytic solution
JP3147277B2 (en) * 1994-10-17 2001-03-19 スズキ株式会社 Spraying condition determination method
JP3182057B2 (en) * 1995-04-28 2001-07-03 株式会社デンソー Fuel injection valve
JP3182059B2 (en) * 1994-08-19 2001-07-03 エイ・ティ・アンド・ティ・コーポレーション Equal access to inter-exchange carriers in mobile wireless packet data communication systems

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03147277A (en) * 1989-11-01 1991-06-24 Sanyo Electric Co Ltd Nonaqueous electrolyte secondary battery
JPH03182057A (en) * 1989-12-08 1991-08-08 Sanyo Electric Co Ltd Manufacture of secondary battery with non-aqueous electrolytic solution
JPH03182059A (en) * 1989-12-11 1991-08-08 Sanyo Electric Co Ltd Secondary battery with non-aqueous electrolytic solution
JP3182059B2 (en) * 1994-08-19 2001-07-03 エイ・ティ・アンド・ティ・コーポレーション Equal access to inter-exchange carriers in mobile wireless packet data communication systems
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JP3182057B2 (en) * 1995-04-28 2001-07-03 株式会社デンソー Fuel injection valve

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