CN109850883A - A kind of preparation method of based quaternary ammonium salt modification supercapacitor graphene dispersing solution - Google Patents
A kind of preparation method of based quaternary ammonium salt modification supercapacitor graphene dispersing solution Download PDFInfo
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- Y02E60/13—Energy storage using capacitors
Abstract
The invention belongs to electrochemical technology fields, more particularly to a kind of preparation method of based quaternary ammonium salt modification supercapacitor graphene dispersing solution, system is dispersed graphene powder or reunion state slurry in solvent by based quaternary ammonium salt, by mechanical dispersion to get purpose product；Based quaternary ammonium salt general structure is as follows:Wherein: m=1,2；n=1,2；The object of the invention product has good wettability and electrochemical stability；For electrode material for super capacitor, the supercapacitor of composition has low internal resistance and high static capacity and excellent cycle characteristics.
Description
Technical field
The invention belongs to electrochemical technology fields more particularly to a kind of based quaternary ammonium salt to modify supercapacitor graphene
The preparation method of dispersion liquid.
Background technique
Graphene has the properties such as excellent electricity, mechanics, optics and calorifics, is widely used in metallic crystal pipe, surpasses
Grade capacitor, nonlinear optical material, nanocomposite carrier, electrochemical sensor, pharmaceutical carrier, hydrogen storage material, gas
The fields such as adsorbent, solar battery.But graphene film interlayer has stronger Van der Waals force, very easy to assemble, and makes it
It is insoluble in water and there are commonly solvent, significantly impacts the performance of graphene performance in practical application.Therefore, in order to sufficiently send out
Its advantageous property is waved, preparing uniform, high stability graphene dispersion system is it in various fields research and applies important
Condition.
A kind of direct preparation method of graphene dispersing solution is that graphite or expanded graphite are applied directly to certain organic solvent
Or in aqueous surfactant solution, certain density single-layer or multi-layer graphite is prepared by ultrasonic wave, heating or the effect of grinding
Alkene solution.Solvent molecule or surfactant molecule pass through the absorption such as pi-pi accumulation and hydrophobic effect on the surface of graphene, and dependence is quiet
Electricity repels or intermolecular force, realizes effective dispersion ((a) X.-L.Li, G.-Y.Zhang, X.-D.Bai, the X.- of graphene
M.Sun,X.-R.Wang,E.-G.Wang,H.-J.Dai,Nat.Nanotechnol.2008,3,538；(b)S.-Z,Zu,B.-
H.Han,J.Phys.Chem.C 2009,113,13651；(c)S.Wang,M.Yi,Z.-G.Shen,X.-J.Zhang,S.-
L.Ma,RSC Adv.,2014,4,25374；(d)C.b.Yeon,S.J.Yun,K.S.Lee,J.W.Lim,Carbon,2014,
83,8 3,136.).The liquid phase Direct dispersion method preparation process of graphene is not related to chemical change, has at low cost, easy to operate
The advantages that, but obtained graphene dispersing solution concentration is lower, is only capable of reaching 0.1% (mass ratio)；Organic solvent is available
The graphene dispersing solution of higher concentration, dispersion concentration can be more than 1% (mass ratio), but at high cost, and its boiling point is higher, is not easy
Remove, thus to final performance, especially electricity and heat performance is adversely affected, therefore limit graphene into
One step application.
Another prepares the method for graphene dispersing solution, is to carry out oxidation processes to graphite first with oxidant, obtains
Modified graphene oxide, then again by reduction obtain it is hydrophilic it is grapheme modified (D.R.Dreyer, S.Park,
C.W.Bielawski,Chem.Soc.Rev.2010,39(1):228.).But strong corrosive, strong oxygen are used in such method
The substance for the property changed, the high requirements on the equipment, and its crystal structure of obtained graphene is also extremely imperfect, with the presence of a large amount of defects,
To limit it in the application of field of functional materials.
Supercapacitor (double layer capacitor) is a kind of high-energy power storage element developed in recent years, is had
High power density, the high circulation service life, can quick impulse electricity and the advantages that no pollution to the environment, be widely used in motor adjusting
Device, sensor, the backup power supply of computer memory, the starter of motor vehicles, wind-power electricity generation and solar power system etc.
Clear energy sources system, thus attract attention.
In recent years, graphene and its derivative become energy storage field research in the research and application in supercapacitor field
Hot spot.And in current graphene dispersion system, it is based on the graphene dispersing solution of organic solvent (DMF, NMP, PVP etc.), by
The production process of list component is caused to complicate in the presence of organic solvent；Though using conventional surfactants as dispersing agent
The aqueous solution of right available graphene dispersion, but the chemical property of the surfactant by being utilized is poor, also greatly
It is limited greatly in the application of energy storage field.Therefore, the good power characteristic of Yao Shixian Graphene electrodes material, high-energy density
With good electrochemical cycle stability, there is an urgent need to the graphene dispersion agent of stable electrochemical property and aqueous dispersion systems
Design, exploitation, this is also an important topic in the research of current graphene.
Summary of the invention
In view of problem of the existing technology prepared by above-mentioned graphene dispersing solution and electrode of super capacitor, the present invention
To be designed to provide a kind of preparation section simple, content is high, and the stable based quaternary ammonium salt of performance modifies supercapacitor stone
The preparation method of black alkene dispersion liquid.
In order to solve the above technical problems, the present invention is implemented as follows:
A kind of preparation method of based quaternary ammonium salt modification supercapacitor graphene dispersing solution, is to pass through based quaternary ammonium salt
It disperses graphene powder or reunion state slurry in solvent, by mechanical dispersion to get purpose product.
As a preferred embodiment, based quaternary ammonium salt general structure of the present invention is as follows:
Wherein: m=1,2；N=1,2.
Further, acid imide and propane sultone or fourth sulfonic acid that based quaternary ammonium salt of the present invention is replaced by amine
The quaternization reaction of lactone is achieved.
Further, for the present invention in terms of mass percentage, the dosage of the based quaternary ammonium salt is 0.1~20%；It is described
The dosage of graphene powder is 0.1~20%.
Further, solvent of the present invention is the mixed of one or more of deionized water, ethyl alcohol or isopropanol
Close object.
Further, mechanical dispersion of the present invention uses high-speed stirred, ultrasonic wave auxiliary stirring or nano-milled.
It is a discovery of the invention that based quaternary ammonium salt is as dressing agent and then dispersed graphite alkene, by acid imide and graphene it
Between π-π interaction the high concentration dispersion of graphene powder or reunion state slurry may be implemented, and obtain stone of good performance
Black alkene dispersion liquid, so that the excellent performance of graphene is given full play in further application.
It has also been found that the graphene dispersing solution of based quaternary ammonium salt modification is introduced in electrode material for super capacitor,
As conductive agent or electrode active material, the electrode material for super capacitor being thus made is conducive to form good conductive mesh
Network, and there is low internal resistance and high static capacity using the supercapacitor that the electrode is constituted.
Based quaternary ammonium salt composition principle of the present invention is as follows:
The acid imide that based quaternary ammonium salt of the present invention is replaced by amine and propane sultone or butyl sultone it is quaternized
Reaction obtains.The acid imide that wherein amine replaces can refer to literature method (H.-X.Wu, H.-X.Wang, L.Xue, Y.Shi, X.-
Y Li J.Phys.Chem.B, 2010,114 (45), 14420.) pass through acid anhydride and N, N- dimethyl-ethylenediamine or N, N- diformazan
It is prepared by the amidation process of base -1,3- propane diamine.
In terms of mass percentage, the dosage of based quaternary ammonium salt of the present invention is 0.1~20%, preferably 0.5~15%；Stone
The dosage of black alkene powder is 1~30%, preferably 5~20%.
Graphene dispersing solution produced by the present invention can be used as the conductive agent or active material of electrode material for super capacitor, together
When can choose and ketjen carbon black, acetylene black, furnace black, carbon fiber VGCF, nano-graphite, carbon nanotube, electrically conductive graphite, high ratio
One or more of surface area activated carbon, carbon fiber are used in mixed way.
Based quaternary ammonium salt of the present invention as dressing agent and then the graphene that disperses, by acid imide and graphene it
Between π-π interaction realize the high-concentration stable dispersion of graphene powder or reunion state slurry.As supercapacitor
Conductive agent is easily formed high-effective conductive network in electrode material, enhances the electric conductivity of pole piece itself, reduces internal resistance, reduces leakage
Electric current；As the electrode active material of supercapacitor, improve the flexibility of pole piece and the wellability of electrolyte, production and
It is not easy to lose powder in process, crack, and improve the cycle performance of the large capacity supercapacitor prepared by the pole piece.
Detailed description of the invention
Present invention will be further explained below with reference to the attached drawings and specific embodiments.Protection scope of the present invention not only office
It is limited to the statement of following content.
Fig. 1 is the aqueous dispersions of graphene prepared by the embodiment of the present invention 1；
Fig. 2 is the scanning electron microscope of the based quaternary ammonium salt surface modification graphene dispersing solution in the embodiment of the present invention 1
Figure.
Specific embodiment
The invention will be further described for following embodiment, but the contents of the present invention are not limited by this embodiment.
Embodiment 1
Prepare N, four carboximide propane sulfonic acid inner salt of N '-two (2-N ", N "-dimethylethyl amine) -3,4,9,10-
(EPPS)
By N, four carboximide (54g, 0.1mol) of N '-two (2-N ", N "-dimethyl ethyl ammonia) -3,4,9,10- and 1,
3-N-morpholinopropanesulfonic acid lactone (24g, 0.2mol) reacts 3 hours at 80 DEG C in glycol dimethyl ether (200mL), cooling, filtering,
Obtain inner salt product (72 grams).
Structural analysis is as follows:
1H NMR(400MHz,CF3CO2D) δ: 8.78 (d, J=12.4Hz, 8H), 4.83-4.94 (m, 4H), 4.63-4.69
(m,4H),3.76-3.81(m,8H),3.42(s,12H),2.52-2.58(m,4H).
MS(ESI)m/z:779[M+H]+.
Prepare graphene dispersing solution
The based quaternary ammonium salt (EPPS) prepared in 8g above-described embodiment 1 and 40g Graphene powder are weighed respectively, and 1000g is added
Deionized water, ultrasonic vibration (power 100W) 30 minutes；Then it is transferred in nano-level grinder, grinds 30 minutes；By the graphene
Mixed liquor is centrifuged.Centrifugal rotational speed 1000rpm is centrifuged 20 minutes, obtains graphene dispersing solution.Weigh the graphite separated
Alkene obtains the graphene dispersing solution that concentration is 3.4g/100g.
As a result as shown in Figure 1, the aterrimus of stable homogeneous is presented in dispersion liquid, the generation not precipitated illustrates a large amount of stone
Black alkene lamella is stabilized in dispersion liquid system system.
Transmission electron microscope Electronic Speculum result (Fig. 2) shows the presence for having a large amount of graphene sheet layer in solution.
Prepare electrode for super capacitor:
Active carbon (100g, specific surface area 1500m are added in ball mill2/ g), acetylene black (5g), carry out the residence time
For 30 minutes milled processeds.Graphene dispersing solution (100g) made from PTFE (6g) and above-mentioned experiment is added, grinds 1 hour,
Electrode slurry is obtained, and is equably coated on metallic aluminium collector, it is 10 minutes dry at 120 DEG C；On press machine, by the electricity
Pole pole piece carries out calendering process, forms 120 microns of thick electrode layers, obtains electrode plates.
The vacuum drying that 5 hours are carried out with 120 DEG C of temperature, is cut to size to obtain electrode for super capacitor.
Embodiment 2
Prepare N, four carboximide fourth acid inner salt of N '-two (2-N ", N "-dimethylethyl amine) -3,4,9,10-
(EPDS)
By N, four carboximide (54g, 0.1mol) of N '-two (2-N ", N "-dimethyl ethyl ammonia) -3,4,9,10- and 1,
4- butyl sultone (27g, 0.2mol) reacts 4 hours at 80 DEG C in glycol dimethyl ether (200mL), cooling, filtering,
Obtain inner salt product (75 grams).
Structural analysis is as follows:
1H NMR(400MHz,CF3CO2D) δ: 8.70 (d, J=12.4Hz, 8H), 4.85-4.93 (m, 4H), 4.65-4.69
(m,4H),3.75-3.80(m,8H),3.48(s,12H),2.21-2.27(m,4H),1.93-1.98(m,4H).
MS(ESI)m/z:807[M+H]+.
Prepare graphene dispersing solution
The pyrenyl quaternary ammonium salt (PEBS) prepared in 8g above-described embodiment 2 and 40g Graphene powder are weighed respectively, and 800g is added and goes
Ionized water 200g ethyl alcohol, high-speed stirred 1 hour；Then it is transferred in nano-level grinder, grinds 30 minutes；By the graphene mixed liquor
It is centrifuged.Centrifugal rotational speed 1000rpm is centrifuged 20 minutes, isolated graphene dispersing solution.Weigh the graphene separated
Particle obtains the graphene dispersing solution that concentration is 3.5g/100g.
Prepare electrode for super capacitor:
Active carbon (100g, specific surface area 1500m are added in ball mill2/ g), ketjen carbon black (2g), acetylene black
(3g) carries out the milled processed that the residence time is 30 minutes.Graphene dispersing solution made from PTFE (6g) and above-mentioned experiment is added
(100g) grinds 1 hour, obtains electrode slurry, and be equably coated on metallic aluminium collector, 10 minutes dry at 120 DEG C；
On press machine, which is subjected to calendering process, 120 microns of thick electrode layers is formed, obtains electrode plates.
The vacuum drying that 5 hours are carried out with 120 DEG C of temperature, is cut to size to obtain electrode for super capacitor.
Embodiment 3
N is prepared, in four carboximide propane sulfonic acid of N '-two (3-N ", N "-dimethyl -1,3- propyl amine) -3,4,9,10-
Salt (PPPS)
By N, four carboximide of N '-two (3-N ", N "-dimethyl -1,3- propyl ammonia) -3,4,9,10- (57g,
0.1mol) reacted 5 hours at 80 DEG C in glycol dimethyl ether (200mL) with 1,3-propane sultone (24g, 0.2mol),
Cooling, filtering obtains inner salt product (72 grams).
Structural analysis is as follows:
1H NMR(400MHz,CF3CO2D) δ: 8.78 (d, J=12.4Hz, 8H), 4.83-4.87 (m, 4H), 4.60-4.67
(m,4H),3.81-3.86(m,8H),3.56(s,12H),2.24-2.37(m,8H).
MS(ESI)m/z:807[M+H]+.
Prepare graphene dispersing solution
The pyrenyl quaternary ammonium salt (PPPS) prepared in 10g above-described embodiment 3 and 45g Graphene powder are weighed respectively, and 800g is added
Deionized water 200g isopropanol is ultrasonically treated 1 hour；Then it is transferred in nano-level grinder, grinds 30 minutes；The graphene is mixed
Liquid is closed to be centrifuged.Centrifugal rotational speed 1000rpm is centrifuged 20 minutes, and isolated supernatant is graphene dispersing solution.It weighs
The graphene particles separated obtain the graphene dispersing solution that concentration is 3.7g/100g.
Prepare electrode for super capacitor:
Active carbon (100g, specific surface area 1500m are added in ball mill2/ g), ketjen carbon black (5g), be detained
The milled processed that time is 30 minutes.Graphene dispersing solution (100g) made from PTFE (6g) and above-mentioned experiment is added, grinding 1 is small
When, electrode slurry is obtained, and be equably coated on metallic aluminium collector, it is 10 minutes dry at 120 DEG C；It, will on press machine
The electrode plates carry out calendering process, form 120 microns of thick electrode layers, obtain electrode plates.
The vacuum drying that 5 hours are carried out with 120 DEG C of temperature, is cut to size to obtain electrode for super capacitor.
Embodiment 4
N is prepared, in four carboximide fourth sulfonic acid of N '-two (3-N ", N "-dimethyl -1,3- propyl amine) -3,4,9,10-
Salt (PPDS)
By N, four carboximide of N '-two (3-N ", N "-dimethyl -1,3- propyl ammonia) -3,4,9,10- (57g,
0.1mol) reacted 5 hours at 80 DEG C in glycol dimethyl ether (200mL) with Isosorbide-5-Nitrae-butyl sultone (27g, 0.2mol),
Cooling, filtering obtains inner salt product (78 grams).
Structural analysis is as follows:
1H NMR(400MHz,CF3CO2D) δ: 8.74 (d, J=12.4Hz, 8H), 4.84-4.87 (m, 4H), 4.63-4.68
(m,4H),3.80-3.85(m,8H),3.60(s,12H),2.41-2.46(m,8H),1.92-1.97(m,4H).
MS(ESI)m/z:835[M+H]+.
Prepare graphene dispersing solution
The pyrenyl quaternary ammonium salt (PPDS) prepared in 8g above-described embodiment 4 and 40g Graphene powder are weighed respectively, and 700g is added and goes
Ionized water 300g isopropanol is ultrasonically treated 1 hour；Then it is transferred in nano-level grinder, grinds 1 hour；The graphene is mixed
Liquid is centrifuged.Centrifugal rotational speed 1000rpm is centrifuged 20 minutes, isolated graphene dispersing solution.Weigh the graphite separated
Alkene particle obtains the graphene dispersing solution that concentration is 3.6g/100g.
Prepare electrode for super capacitor:
Active carbon (100g, specific surface area 1500m are added in ball mill2/ g), carbon nanotube (2g), acetylene black
(3g) carries out the milled processed that the residence time is 30 minutes.Graphene dispersing solution made from PTFE (6g) and above-mentioned experiment is added
(100g) grinds 1 hour, obtains electrode slurry, and be equably coated on metallic aluminium collector, 10 minutes dry at 120 DEG C；
On press machine, which is subjected to calendering process, 120 microns of thick electrode layers is formed, obtains electrode plates.
The vacuum drying that 5 hours are carried out with 120 DEG C of temperature, is cut to size to obtain electrode for super capacitor.
Comparative example 1
In ball mill be added active carbon (100 grams, specific surface area 1500m2/ g), acetylene black (5 grams), when being detained
Between be 30 minutes milled processeds.PTFE (6 grams) and graphene powder (4 grams) is added, grinds 1 hour, obtains electrode slurry,
The preparation of electrode carries out in the same manner as shown in Example 1.
Comparative example 2
In ball mill be added active carbon (100 grams, specific surface area 1500m2/ g), ketjen carbon black (1 gram), acetylene black
(4 grams) carry out the milled processed that the residence time is 30 minutes.PTFE (6 grams) and graphene powder (4 grams) is added, grinding 1 is small
When, electrode slurry is obtained,
The preparation of electrode carries out in the same manner as shown in Example 1.
Performance of the supercapacitor test
Using the electrode plates prepared in the embodiment and comparative example as working electrode, aluminium foil is current collection collection, polytetrafluoroethyl-ne
Alkene is diaphragm, and the acetonitrile solution of 1.0M triethylmethylammonium tetrafluoroborate makees electrolyte assembling supercapacitor.In 1.2-
In the range of 2.5V, loop test is carried out at constant current (5mA), determines its capacity and interior by charging and discharging curve at room temperature
Resistance, and the capacity ratio for calculating the capacity after carrying out 200 circulations and recycling for the first time.Test result is listed in table -1.
Table -1
The system of supercapacitor is used for by the grapheme modified obtained dispersion liquid of based quaternary ammonium salt as can be seen from Table 1
Standby, specific capacitance improves 30% before relatively modifying, internal resistance reduces 60%, and maintains good efficiency for charge-discharge.
Based quaternary ammonium salt water system graphene dispersing solution made from the method for the present invention, graphene content is up to 3% (mass ratio)
More than, based quaternary ammonium salt is not only dispersing agent and stabilizer of good performance, while also improving the electric conductivity of dispersion liquid.This method
Preparation process is simple, low in cost, is easy to industrialization production, is application of the graphene in supercapacitor and related energy storage field
Provide good development prospect.
Above with respect to specific descriptions of the invention, it is merely to illustrate the present invention and is not limited to the embodiment of the present invention and is retouched
The technical solution stated.Those skilled in the art should understand that still can modify to the present invention or equivalent replacement,
To reach identical technical effect.Needs are used as long as meeting, all in the protection scope of invention.
Claims (6)
1. a kind of preparation method of based quaternary ammonium salt modification supercapacitor graphene dispersing solution, which is characterized in that pass through
Based quaternary ammonium salt disperses graphene powder or reunion state slurry in solvent, by mechanical dispersion to get purpose product.
2. the preparation method of based quaternary ammonium salt modification supercapacitor graphene dispersing solution according to claim 1,
It is characterized in that, the based quaternary ammonium salt general structure is as follows:
Wherein: m=1,2； n = 1, 2.
3. the preparation method of based quaternary ammonium salt modification supercapacitor graphene dispersing solution according to claim 2,
Be characterized in that: acid imide and propane sultone that the based quaternary ammonium salt is replaced by amine or butyl sultone it is quaternized anti-
It should be achieved.
4. the preparation method of based quaternary ammonium salt modification supercapacitor graphene dispersing solution according to claim 3,
Be characterized in that: in terms of mass percentage, the dosage of the based quaternary ammonium salt is 0.1~20%；The dosage of the graphene powder
It is 0.1~20%.
5. based quaternary ammonium salt according to claim 4 modifies supercapacitor graphene
The preparation method of dispersion liquid, it is characterised in that: the solvent is deionized water, ethyl alcohol or isopropyl
The mixture of one or more of alcohol.
6. based quaternary ammonium salt according to claim 5 modifies supercapacitor graphene
The preparation method of dispersion liquid, it is characterised in that: the mechanical dispersion uses high-speed stirred, ultrasound
Wave auxiliary stirring or nano-milled.
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Cited By (5)
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| CN110127683A (en) * | 2019-06-19 | 2019-08-16 | 哈尔滨万鑫石墨谷科技有限公司 | A kind of graphene dispersing solution and its preparation method and application |
| CN112442034A (en) * | 2020-12-02 | 2021-03-05 | 中国科学院化学研究所 | Novel conjugated micromolecule inner salt containing sulfonate quaternary ammonium salt and preparation method and application thereof |
| CN113755022A (en) * | 2020-06-03 | 2021-12-07 | 重庆科技学院 | Water-soluble diionic perylene bisimide dye, synthesis method and application of cell fluorescent marker |
| WO2022250461A1 (en) * | 2021-05-28 | 2022-12-01 | 주식회사 엘지에너지솔루션 | Conductive material dispersion |
| CN115777719A (en) * | 2022-10-08 | 2023-03-14 | 浙江省海洋开发研究院 | Perylene quaternary ammonium salt-graphene composite antibacterial agent and preparation method thereof |
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| CN102360960A (en) * | 2011-10-14 | 2012-02-22 | 渤海大学 | Super capacitor electrode material and super capacitor electrode production method |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110127683A (en) * | 2019-06-19 | 2019-08-16 | 哈尔滨万鑫石墨谷科技有限公司 | A kind of graphene dispersing solution and its preparation method and application |
| CN110127683B (en) * | 2019-06-19 | 2023-04-11 | 哈尔滨万鑫石墨谷科技有限公司 | Graphene dispersion liquid and preparation method and application thereof |
| CN113755022A (en) * | 2020-06-03 | 2021-12-07 | 重庆科技学院 | Water-soluble diionic perylene bisimide dye, synthesis method and application of cell fluorescent marker |
| CN112442034A (en) * | 2020-12-02 | 2021-03-05 | 中国科学院化学研究所 | Novel conjugated micromolecule inner salt containing sulfonate quaternary ammonium salt and preparation method and application thereof |
| CN112442034B (en) * | 2020-12-02 | 2022-02-11 | 中国科学院化学研究所 | Conjugated small-molecule inner salt containing sulfonate quaternary ammonium salt and preparation method and application thereof |
| WO2022250461A1 (en) * | 2021-05-28 | 2022-12-01 | 주식회사 엘지에너지솔루션 | Conductive material dispersion |
| CN115777719A (en) * | 2022-10-08 | 2023-03-14 | 浙江省海洋开发研究院 | Perylene quaternary ammonium salt-graphene composite antibacterial agent and preparation method thereof |
| CN115777719B (en) * | 2022-10-08 | 2024-04-19 | 浙江省海洋开发研究院 | Perylene quaternary ammonium salt-graphene composite antibacterial agent and preparation method thereof |
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