CN113555554B - Binder, silicon-carbon negative plate and preparation method thereof - Google Patents
Binder, silicon-carbon negative plate and preparation method thereof Download PDFInfo
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- CN113555554B CN113555554B CN202110619579.XA CN202110619579A CN113555554B CN 113555554 B CN113555554 B CN 113555554B CN 202110619579 A CN202110619579 A CN 202110619579A CN 113555554 B CN113555554 B CN 113555554B
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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
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/62—Selection of inactive substances as ingredients for active masses, e.g. binders, fillers
- H01M4/621—Binders
- H01M4/622—Binders being polymers
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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
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
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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
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/04—Processes of manufacture in general
- H01M4/0402—Methods of deposition of the material
- H01M4/0404—Methods of deposition of the material by coating on electrode collectors
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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
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/13—Electrodes for accumulators with non-aqueous electrolyte, e.g. for lithium-accumulators; Processes of manufacture thereof
- H01M4/134—Electrodes based on metals, Si or alloys
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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
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/13—Electrodes for accumulators with non-aqueous electrolyte, e.g. for lithium-accumulators; Processes of manufacture thereof
- H01M4/139—Processes of manufacture
- H01M4/1395—Processes of manufacture of electrodes based on metals, Si or alloys
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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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- 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 discloses a binder, which is prepared by copolymerizing dianhydride monomer, diamine monomer and polyoxypropylene polyamine to prepare amino-terminated polyamic acid, then carrying out isocyanate group end capping by using a capping agent, and then carrying out imidization. The invention also discloses a silicon-carbon negative plate and a preparation method thereof. According to the invention, the polypropylene oxide polyamine is introduced into the main chain, urea groups are grafted at two ends of the main chain, and then the polypropylene oxide is decomposed through imidization and heat, so that the adhesive property and the buffer property of the binder are improved, and a cross-linked network can be repeatedly formed in the charging and discharging processes, so that the problem of volume expansion of the negative plate is greatly improved, the falling-off of the silicon-carbon active substance can be prevented, the full contact between the electrolyte and the active substance is promoted, and the battery performance is improved.
Description
Technical Field
The invention relates to the technical field of binders, and particularly relates to a binder, a silicon-carbon negative plate and a preparation method thereof.
Background
Lithium ion batteries are widely used in portable electronic devices such as mobile phones and computers due to their advantages such as good cycle performance, high energy density, and high safety. However, with the development of new energy vehicles and new portable electronic products, new challenges are posed to the energy density of lithium ion batteries. The use of conventional graphite as a negative electrode material has not been able to meet the market demand, and development of a negative electrode material having a higher specific capacity is urgently needed.
Silicon is known as the material with the highest theoretical specific capacity, has abundant reserves, and is considered to be one of the most potential novel anode materials. The theoretical specific capacity of silicon (Si) can reach 4200mAh/g (the lithium intercalation product is Li) 4.4 Si), but the expansion rate of the silicon negative electrode reaches 300% along with huge volume change in the charging and discharging processes, and huge stress generated by excessive volume expansion can cause pulverization of silicon particles, cracking of a solid electrolyte interface film (SEI film), cracking of a pole piece and the like, so that the capacity of Si is irreversibly attenuated, and the cycle performance of the silicon negative electrode is seriously influenced. How to improve the cycle performance of the silicon anode is a primary problem to be solved.
Besides the improvement of the particle structure and the surface coating, the cycle characteristic of the Si powder can be improved, and the cycle stability of the Si powder can be greatly improved by adopting the electrolyte and the binder which are matched with the Si cathode material. Polyvinylidene fluoride (PVDF) resin is a binder of anode and cathode materials of a lithium ion battery which is widely applied, has good stability, but has weak bonding strength and tensile strength of about 55MPa, can only adapt to volume expansion with expansion rate within 10 percent, and is difficult to apply to a Si cathode.
Disclosure of Invention
Based on the technical problems existing in the background technology, the invention provides the binder, the silicon-carbon negative plate and the preparation method thereof, and the invention improves the adhesive property and the buffer property of the binder by introducing polypropylene oxide polyamine into a main chain, grafting urea groups at two ends of the main chain, and then decomposing the polypropylene oxide through imidization and thermal decomposition, and can repeatedly form a cross-linked network in the charging and discharging processes, thereby greatly improving the volume expansion problem of the negative plate, preventing the silicon-carbon active substance from falling off, promoting the full contact of electrolyte and the active substance, and improving the battery performance.
The invention provides a binder, which is prepared by copolymerizing dianhydride monomer, diamine monomer and polyoxypropylene polyamine to prepare amino-terminated polyamic acid, then carrying out isocyanate group end capping by using a capping agent, and then carrying out imidization.
The copolymerization is carried out to obtain amino-terminated polyamic acid, and then the end capping agent is used for carrying out end capping on isocyanate groups, which are all carried out in the atmosphere of inert gas; preferably copolymerizing at 30-50 ℃ for 10-15h to obtain amino-terminated polyamic acid; preferably at 60-80 ℃ for 2-4h for isocyanate group blocking; the amino-terminated polyamic acid refers to an amino-terminated polyamic acid.
Preferably, the polyoxypropylene polyamine has the formula:
wherein R is an alkylene group having 2 or more carbon atoms.
Preferably, the molecular weight of the polyoxypropylene polyamine is 300-500.
According to the invention, polyoxypropylene polyamine is copolymerized with diamine monomer and dianhydride monomer, a polyoxypropylene chain segment is introduced into a main chain of polyamic acid, and an imine group is introduced, so that a strong hydrogen bond can be formed between the polyoxypropylene chain segment and silicon-carbon active substance particles, thus the interaction between a binder and the silicon-carbon active substance is improved, and the adhesion strength is improved; in addition, polypropylene oxide can be thermally decomposed in the imidization process to form a porous structure, so that the buffer performance of the binder is improved, the problem of volume expansion of the negative plate in the charge-discharge process is solved, the full contact between the electrolyte and the active substance can be promoted, and the battery performance is improved.
The specific preparation steps of the polyoxypropylene polyamine can refer to a method disclosed in the literature, "synthesis and characterization of polyoxypropylene polyamine and toughening effect on epoxy resin", and the specific steps are as follows: in the presence of pyridine, polypropylene oxide dihydric alcohol reacts with p-toluenesulfonyl chloride to obtain disulfonated polyether, and then the disulfonated polyether and diamine are subjected to aminolysis reaction under the protection of inert gas to obtain polypropylene oxide polyamine, wherein the diamine is preferably aliphatic diamine, such as ethylene diamine, propylene diamine, butylene diamine, pentylene diamine, hexylene diamine and the like.
Preferably, the blocking agent is a substance containing one isocyanate group.
The blocking agent may be: at least one of p-toluene isocyanate, phenyl isocyanate, p-isopropyl phenyl isocyanate, isocyanate propyl triethoxysilane, isocyanate propyl trimethoxysilane and the like.
The amino-terminated polyamic acid reacts with a blocking agent containing isocyanate groups to form urea groups at two ends of a main chain, reversible hydrogen bond breakage and reconnection are carried out between the urea groups in the charging and discharging process, a cross-linking network is repeatedly formed, and the problem of volume expansion of the negative plate is solved; and can prevent the silicon carbon active material from falling off and improve the cycle performance of the battery.
Preferably, the procedure for imidization is: keeping the temperature for 1-1.5h at 60-80 deg.C, 100-120 deg.C, 200-220 deg.C, and 250-270 deg.C respectively.
Preferably, the polyoxypropylene polyamine comprises 4-8% of the total weight of dianhydride monomer and diamine monomer.
The proper amount of the polyoxypropylene polyamine content can ensure that the adhesive has good buffering performance and simultaneously keeps better adhesion and strength.
Preferably, the molar ratio of the dianhydride monomer to the diamine monomer is 1.05 to 1.1.
Preferably, the molar ratio of dianhydride monomer to capping agent is 1.06 to 1.11.
In the preparation process of the amino-terminated polyamic acid, the dianhydride monomer may be: <xnotran> 4,4' - ( ) ,5- (2,5- -3- ) -3- - -1,2- , ,1,2,3,4- ,3,3', 4,4' - ,2,2 ',3,3' - ,3,3', 4,4' - ,3,3', 4,4' - ,2,2 ',3,3' - , -4,4' - ,1,1- -4,4' - ,2,2- -4,4' - ,1,2- -4,4' - ,1,3- -4,4' - ,1,4- -4,4' - ,1,5- -4,4' - ,4,4' - , -4,4' - , -4,4' - ,1,3- (3,4- ) ,1,3- (3,4- ) ,1,4- (3,4- ) ,1,3- [2- (3,4- ) -2- ] ,1,4- [2- (3,4- ) -2- ] , </xnotran> Bis [3- (3, 4-dicarboxyphenoxy) phenyl ] methane dianhydride, bis [4- (3, 4-dicarboxyphenoxy) phenyl ] methane dianhydride, 2-bis [3- (3, 4-dicarboxyphenoxy) phenyl ] propane dianhydride, 2-bis [4- (3, 4-dicarboxyphenoxy) phenyl ] propane dianhydride, bis (3, 4-dicarboxyphenoxy) dimethylsilane dianhydride, 1, 3-bis (3, 4-dicarboxyphenyl) -1, 3-tetramethyldisiloxane dianhydride, 2,3,6, 7-naphthalenetetracarboxylic dianhydride, 1,4,5, 8-naphthalenetetracarboxylic dianhydride, 1,2,5, 6-naphthalenetetracarboxylic dianhydride, 3,4,9, 10-perylenetetracarboxylic dianhydride, 2,3,6, 7-anthracenetetracarboxylic dianhydride, 1,2,7, 8-phenanthrenetetracarboxylic dianhydride, etc.; among them, 4,4' - (hexafluoroisopropylidene) diphthalic anhydride, pyromellitic dianhydride, 3,3',4,4' -benzophenonetetracarboxylic dianhydride, and the like are preferable; these dianhydride monomers may be used alone or in combination of two or more;
the diamine monomer may be: 4,4' -diaminodiphenyl ether (ODA for short), 2' -dimethyl-4, 4' -diaminobiphenyl, 1, 4-bis (4-aminophenoxy) benzene, 2-bis (4- (4-aminophenoxy) phenyl) propane, 1, 4-bis (4-amino-2-trifluoromethylphenoxy) benzene, 2-bis [4- (4-aminophenoxy) phenyl ] propane, 4' -bis (4-aminophenoxy) biphenyl, 2,2' -bis (trifluoromethyl) -4,4' -diaminobiphenyl, 4' -diaminobenzanilide, 4-aminophenyl-4-aminobenzoate, bis (4-aminophenyl) terephthalate, bis (4- (4-aminophenoxy) phenyl) sulfone, bis (4-amino-3-carboxyphenyl) methane, 4' -diaminodiphenyl sulfone, 4' -diaminobenzophenone, and the like; among them, preferred are 4,4' -diaminodiphenyl ether, 4' -diaminodiphenyl sulfone, 4' -diaminobenzophenone, 2' -dimethyl-4, 4' -diaminobiphenyl, 1, 4-bis (4-amino-2-trifluoromethylphenoxy) benzene, and the like; these diamine monomers may be used alone or in combination of two or more.
The appropriate diamine monomer and dianhydride monomer are selected, so that the performances of the negative plate such as resistance, electrolyte compatibility and the like can be further improved.
The invention also provides a silicon-carbon negative plate, which comprises: the current collector and the negative electrode material, the raw materials of the negative electrode material comprise the following components in parts by weight: 7 parts of silicon-carbon active substance, 2-2.5 parts of conductive agent and 0.5-1 part of binder, wherein the binder is the binder.
The conductive agent may be: at least one of conductive carbon black, acetylene black, graphene, carbon nanotubes, carbon fibers, and the like.
The invention also provides a preparation method of the silicon-carbon negative plate, which comprises the following steps: in an inert gas atmosphere, copolymerizing a dianhydride monomer, a diamine monomer and polyoxypropylene polyamine in an organic solution to prepare an amino-terminated polyamide acid solution, and then reacting with a blocking agent to carry out isocyanate group blocking to obtain a solution A; and uniformly mixing the solution A with a silicon-carbon active substance and a conductive agent, coating the mixture on the surface of a current collector, and imidizing to obtain the silicon-carbon negative plate.
According to the invention, through introducing polypropylene oxide polyamine into the main chain, grafting urea groups at two ends of the main chain, and then decomposing polypropylene oxide through imidization and thermal decomposition, the adhesion performance and the buffer performance of the binder are improved, and a crosslinking network can be repeatedly formed in the charging and discharging processes, so that the problem of volume expansion of the negative plate is greatly improved, the falling-off of a silicon-carbon active substance can be prevented, the full contact between an electrolyte and the active substance is promoted, and the battery performance is improved.
Detailed Description
The technical solution of the present invention will be described in detail below with reference to specific examples.
Example 1
A preparation method of a silicon-carbon negative plate comprises the following steps:
putting polyoxypropylene diol PPO-204, tetrahydrofuran and p-toluenesulfonyl chloride into a four-neck flask, stirring for dissolving, then dropping pyridine, controlling the temperature to be less than 30 ℃, and stirring for reacting for 24 hours to obtain a disulfonated polyether solution; then under the protection of nitrogen, dripping the disulfonated polyether solution into a four-neck flask containing ethylenediamine and toluene, carrying out aminolysis reaction at 110 ℃, and filtering to obtain light yellow polyoxypropylene polyamine (the molecular weight of which is 300-500);
dissolving 10.5mmol of 4,4' -diaminodiphenyl ether and 0.18g of polyoxypropylene polyamine in 30ml of N-methylpyrrolidone, introducing nitrogen to remove air, adding pyromellitic dianhydride (the total mole is 10 mmol) for three times, keeping the temperature and stirring at 50 ℃ for 12 hours to obtain an amino-terminated polyamic acid solution, adding 10.6mmol of p-toluene isocyanate, heating to 70 ℃, keeping the temperature and reacting for 3 hours, and adjusting the solid content to 10wt% to obtain a solution A; and (3) uniformly mixing 10g of the solution A, 7g of the silicon-carbon active substance and 2g of acetylene black, coating the mixture on the surface of the copper foil, and preserving heat for 1.5 hours at 60 ℃, 100 ℃, 200 ℃ and 250 ℃ respectively to obtain the silicon-carbon negative plate.
Example 2
A preparation method of a silicon-carbon negative plate comprises the following steps:
the polyoxypropylene polyamine was prepared as in example 1;
dissolving 11mmols of 4,4' -diaminodiphenyl sulfone and 0.39g of polyoxypropylene polyamine in 30ml of N-methyl pyrrolidone, introducing nitrogen to remove air, adding pyromellitic dianhydride (the total mole is 10 mmol) for three times, keeping the temperature and stirring at 50 ℃ for 12 hours to obtain an amino-terminated polyamic acid solution, adding 11.1mmol of p-isopropylphenyl isocyanate, heating to 70 ℃, keeping the temperature and reacting for 3 hours, and adjusting the solid content to 10 weight percent to obtain a solution A; and uniformly mixing 5g of the solution A, 7g of the silicon-carbon active substance and 2.5g of acetylene black, coating the mixture on the surface of the copper foil, and preserving heat for 1h at 80 ℃, 120 ℃, 220 ℃ and 270 ℃ respectively to obtain the silicon-carbon negative plate.
Example 3
A preparation method of a silicon-carbon negative plate comprises the following steps:
the polyoxypropylene polyamine was prepared as in example 1;
dissolving 10.7mmol of 1, 4-bis (4-amino-2-trifluoromethylphenoxy) benzene and 0.47g of polyoxypropylene polyamine in 30ml of N-methylpyrrolidone, introducing nitrogen to remove air, adding 3,3', 4' -benzophenone tetracarboxylic dianhydride (the total mole number is 10 mmol) in three times, keeping the temperature and stirring at 50 ℃ for 12 hours to obtain an amino-terminated polyamic acid solution, adding 10.8mmol of isocyanate propyl triethoxysilane, heating to 70 ℃, keeping the temperature and reacting for 3 hours, and adjusting the solid content to 10wt% to obtain a solution A; and (3) uniformly mixing 10g of the solution A, 7g of the silicon-carbon active substance and 2g of acetylene black, coating the mixture on the surface of the copper foil, and preserving heat for 1.5 hours at 70 ℃, 110 ℃, 210 ℃ and 260 ℃ respectively to obtain the silicon-carbon negative plate.
Example 4
A preparation method of a silicon-carbon negative plate comprises the following steps:
the polyoxypropylene polyamine was prepared as in example 1;
dissolving 10.8mmol of 4,4 '-diaminobenzophenone and 0.34g of polyoxypropylene polyamine in 30ml of N-methylpyrrolidone, introducing nitrogen to remove air, adding 4,4' - (hexafluoroisopropylidene) diphthalic anhydride (the total mole number is 10 mmol) in three times, keeping the temperature and stirring at 50 ℃ for 12 hours to obtain an amino-terminated polyamic acid solution, adding 11mmol of p-toluene isocyanate, heating to 70 ℃, keeping the temperature and reacting for 3 hours, and adjusting the solid content to 10 weight percent to obtain a solution A; and (3) uniformly mixing 7g of the solution A, 7g of the silicon-carbon active substance and 2.3g of acetylene black, coating the mixture on the surface of the copper foil, and preserving heat for 1.3 hours at 65 ℃, 115 ℃, 205 ℃ and 265 ℃ respectively to obtain the silicon-carbon negative plate.
Comparative example 1
The procedure is as in example 3 except that no polypropyleneoxide polyamine is added.
Comparative example 2
The procedure of example 3 was repeated except that p-tolylene isocyanate was not added.
Comparative example 3
The procedure is as in example 3 except that no polypropyleneoxide polyamine is added and no p-tolylene isocyanate is added.
Comparative example 4
The adhesive is polyvinylidene fluoride, and the weight ratio of the silicon-carbon active substance to the acetylene black to the polyvinylidene fluoride is 7.
Experiment of
Taking the negative electrode sheets prepared in the examples 1-4 and the comparative examples 1-4, and taking a lithium sheet as a positive electrode, celgard2400 as a separator, and a mixed solution of EC and EMC (v/v = 1) of 1mol/LLIPF6 as an electrolyte solution, respectively assembling to obtain the button cell. The charge and discharge tests were performed on the button cells obtained in the above examples and comparative examples, and the results are shown in table 1.
TABLE 1 test results
As can be seen from Table 1, the expansion rate of the silicon-carbon negative plate prepared by the invention is far smaller than that of the silicon-carbon negative plate prepared by the comparative examples 1-4; after 100 times of charging and discharging at 0.1C, the capacity retention rate is more than 75%, which is much higher than that of comparative examples 1-4.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.
Claims (3)
1. The adhesive is characterized in that amino-terminated polyamide acid is prepared by copolymerizing dianhydride monomer, diamine monomer and polyoxypropylene polyamine, then carrying out isocyanate group end capping by using a capping agent, and then carrying out imidization;
the structural formula of the polyoxypropylene polyamine is:
wherein R is an alkylene group with a carbon atom number more than or equal to 2;
the molecular weight of the polyoxypropylene polyamine is 300-500;
the blocking agent is a substance containing one isocyanate group;
the procedure for imidization was: keeping the temperature for 1-1.5h at 60-80 deg.C, 100-120 deg.C, 200-220 deg.C, and 250-270 deg.C respectively;
the polyoxypropylene polyamine accounts for 4-8% of the total weight of the dianhydride monomer and the diamine monomer;
the molar ratio of the dianhydride monomer to the diamine monomer is 1.05-1.1;
the molar ratio of the dianhydride monomer to the end-capping agent is 1.06-1.11.
2. A silicon-carbon negative electrode sheet, comprising: the cathode material comprises the following raw materials in parts by weight: 7 parts of silicon-carbon active substance, 2-2.5 parts of conductive agent and 0.5-1 part of binder, wherein the binder is the binder in claim 1.
3. The preparation method of the silicon-carbon negative electrode plate as set forth in claim 2, characterized by comprising the steps of: in an inert gas atmosphere, copolymerizing a dianhydride monomer, a diamine monomer and polyoxypropylene polyamine in an organic solution to prepare an amino-terminated polyamide acid solution, and then reacting with a blocking agent to perform isocyanate group blocking to obtain a solution A; and uniformly mixing the solution A with a silicon-carbon active substance and a conductive agent, coating the mixture on the surface of a current collector, and imidizing to obtain the silicon-carbon negative plate.
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