CN116003846A - GEMA-MMA copolymer dielectric film and preparation method and application thereof - Google Patents

GEMA-MMA copolymer dielectric film and preparation method and application thereof Download PDF

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CN116003846A
CN116003846A CN202211718111.7A CN202211718111A CN116003846A CN 116003846 A CN116003846 A CN 116003846A CN 202211718111 A CN202211718111 A CN 202211718111A CN 116003846 A CN116003846 A CN 116003846A
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gema
dielectric film
mma copolymer
mma
preparation
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刘雷鹏
贠浩辰
张康宁
吉喆
陈晓飞
段远多
吕生华
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Shaanxi University of Science and Technology
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Abstract

The invention discloses a GEMA-MMA copolymer dielectric film, a preparation method and application thereof, and belongs to the technical field of polymer-based dielectric materials. According to the preparation method, the biomass raw material Guaiacol (GA) which takes lignin as a source is adopted, the guaiacol methacrylate (GEMA) is prepared through esterification reaction, and the GEMA and the Methyl Methacrylate (MMA) are copolymerized to obtain the GEMA-MMA copolymer dielectric film, so that the polarization strength and the breakdown strength can be effectively improved, and the energy storage density of the polymer is further effectively improved. The preparation method is simple and good in repeatability, and can improve the breakdown strength and the energy storage density by controlling the mole ratio of the GEMA to MMA, so that the energy storage efficiency of the polymer is increased, and the preparation method can be used for improving the breakdown strength and the energy storage density of the film capacitor.

Description

GEMA-MMA copolymer dielectric film and preparation method and application thereof
Technical Field
The invention belongs to the technical field of polymer-based dielectric materials, and particularly relates to a GEMA-MMA copolymer dielectric film, a preparation method and application thereof.
Background
In recent years, effective utilization and storage of various energy sources have become an urgent study subject, and a polymer film capacitor, as a physical energy storage device, has the advantages of ultra-high power density, capability of extremely fast energy storage and release, and the like, and is widely applied to the fields of capacitors, pulse power technology, electric vehicle technology, and the like.
The most widely used commercial film capacitor is biaxially oriented polypropylene (BOPP) film which has high breakdown strength but very low energy storage density of 2-4J/cm 3 The method comprises the steps of carrying out a first treatment on the surface of the Polyvinylidene fluoride (PVDF) and its copolymers belong to nonlinear dielectrics, and compared with other materials, the polyvinylidene fluoride (PVDF) has very high dielectric constant and is widely studied, but the high polarization loss and the poor charge and discharge efficiency make the polyvinylidene fluoride (PVDF) limited in the field of dielectric material energy storage; guaiacol, also known as 2-methoxyphenol, which is derived from lignin, is a natural organic substance, has special fragrance, and is widely applied to the fields of fragrances and medicines, but has little application in the field of electronic materials, and has the potential of being applied to the field of dielectric materials by performing functional modification on the guaiacol. The guaiacol molecular structure contains polar group phenolic hydroxyl, guaiacol can be modified by an organic synthesis method to prepare polymerizable monomers of the guaiacol structure, and the structural advantages of benzene rings and ester groups are contained, and delta-pi bonds interact to improve energy storage density and reduce energy loss.
Polymethyl methacrylate (PMMA) is a common organic polymer, also called organic glass, and can be used as a linear dielectric material, but the breakdown strength of PMMA is relatively low, ester groups in a PMMA molecular chain are polar groups, and strong coupling force exists between adjacent polar groups, so that relaxation is caused, high dielectric loss is caused, and the application of the PMMA in the dielectric field is limited due to low energy storage density. Therefore, it is necessary to conduct modification research to increase the energy storage density thereof.
Disclosure of Invention
In order to overcome the defects in the prior art, the invention aims to provide a GEMA-MMA copolymer dielectric film, and a preparation method and application thereof, so as to solve the problem that the existing methyl methacrylate has high dielectric loss and low energy storage density.
In order to achieve the above purpose, the invention is realized by adopting the following technical scheme:
the invention discloses a preparation method of a GEMA-MMA copolymer dielectric film, which comprises the following steps:
1) Mixing guaiacol, methacrylic anhydride and an esterifying agent uniformly, reacting in an inert atmosphere, cooling to room temperature, diluting with dichloromethane, washing, and freeze-drying to obtain GEMA;
2) Dissolving methyl methacrylate and GEMA prepared in the step 1) in DMF, adding an initiator, reacting in an inert atmosphere, purifying, heating and drying to obtain the GEMA-MMA copolymer dielectric film.
Preferably, in step 2), the molar ratio of GEMA to methyl methacrylate is 1 (6-10).
Preferably, in the step 2), the inert atmosphere is argon, the reaction temperature is 80 ℃, and the reaction time is 12 hours.
Preferably, in step 2), purification is carried out by precipitation with methanol and heating at 80℃for 12h.
Preferably, in step 1), guaiacol: the molar ratio of methacrylic anhydride is: 2:2:1.
Preferably, in step 1), the esterifying agent is DMAP, the mole percentage of DMAP being 2mol%.
Preferably, in step 1), the inert atmosphere is argon and the reaction time is 24 hours.
Preferably, in step 1), the washing conditions are: sequentially with saturated NaHCO 3 The aqueous solution, 1mol/L NaOH aqueous solution, 0.5mol/L NaOH aqueous solution, 1.0mol/L HCl aqueous solution and deionized water were washed.
The invention also discloses a GEMA-MMA copolymer dielectric film prepared by the preparation method, the thickness of the GEMA-MMA copolymer dielectric film is 5-15 mu m, the electric breakdown strength is 911.2-638.6 MV/m, and the energy storage density is 8.0-9.0J/cm 3 The energy efficiency is 87.5% -92%.
The invention also discloses application of the GEMA-MMA copolymer dielectric film in preparation of a metallized film capacitor.
Compared with the prior art, the invention has the following beneficial effects:
the invention discloses a preparation method of a GEMA-MMA copolymer dielectric film, which adopts biomass Guaiacol (GA) as a raw material, prepares guaiacol methacrylate (GEMA) through esterification reaction with methacrylic anhydride, reduces strong coupling force between adjacent polar groups through introducing benzene rings into the GEMA, reduces high dielectric loss caused by relaxation, and improves the problem of low PMMA energy storage density; the GEMA-MMA copolymer dielectric film is obtained by copolymerizing guaiacyl methacrylate (GEMA) and Methyl Methacrylate (MMA), and the flexibility and dipole polarization of dipoles are increased on the molecular level by introducing a flexible section into the skeleton of the polar aromatic polymer with a rigid structure, so that the obtained GEMA-MMA copolymer dielectric film effectively improves the polarization strength and the breakdown strength, further effectively improves the energy storage density, and the whole preparation method is simple and good in repeatability.
Further, the breakdown strength and the energy storage density of the dielectric film of the GEMA-MMA copolymer are further improved by controlling the ratio of the GEMA to the MMA, so that the energy storage efficiency of the polymer is further improved.
Further, the reaction is carried out in the argon atmosphere, so that the oxygen in the bottle can be effectively removed;
further, the impurities in the solvent can be effectively removed by methanol precipitation and purification, and the pure GEMA-MMA copolymer dielectric film can be obtained.
The invention also discloses a GEMA-MMA copolymer dielectric film prepared by the preparation method, the thickness of the GEMA-MMA copolymer dielectric film is 5-15 mu m, the breakdown strength of the dielectric film is 911.2-638.6 MV/m, and the energy storage density is 8.0-9.0J/cm 3 The energy efficiency is 87.5% -92%, and the breakdown strength and the energy storage density of the film capacitor can be effectively improved.
The invention also discloses the application of the GEMA-MMA copolymer dielectric film in preparing the metallized film capacitor, firstly, the metallized film capacitor which is most widely used in commercialization at present is a BOPP film capacitor, the energy storage density of which is very low and is only about 2-3J/cm 3 The dielectric film of the GEMA-MMA copolymer greatly improves the energy storage density and the energy storage efficiency; secondly, PVDF-based polymers and BOPP polymers which are non-renewable and non-biodegradable petroleum derived synthetic polymers are widely used in dielectric materials; the invention utilizes the environment-friendly biomass material guaiacol, and prepares the dielectric film by modifying the biomass material guaiacol, thereby having long-term significance for protecting the environment.
Drawings
FIG. 1 is a schematic illustration of the preparation of GEMA according to the invention;
FIG. 2 is a schematic illustration of the preparation of a dielectric film of a GEMA-MMA copolymer of the invention;
FIG. 3 shows dielectric films of GEMA-MMA copolymers of different molar ratios according to the invention 1 H NMR spectrum schematic;
FIG. 4 is a schematic of FT-IR spectra of dielectric films of GEMA-MMA copolymers of different molar ratios according to the invention;
FIG. 5 is a schematic diagram showing the electric displacement-electric field (D-E) curve of a dielectric film of a GEMA-MMA copolymer (GEMA: MMA molar ratio: 1:9) produced in example 2 of the present invention.
Detailed Description
In order that those skilled in the art will better understand the present invention, a technical solution in the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in which it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the present invention without making any inventive effort, shall fall within the scope of the present invention.
It should be noted that the terms "first," "second," and the like in the description and the claims of the present invention and the above figures are used for distinguishing between similar objects and not necessarily for describing a particular sequential or chronological order. It is to be understood that the data so used may be interchanged where appropriate such that the embodiments of the invention described herein may be implemented in sequences other than those illustrated or otherwise described herein. Furthermore, the terms "comprises," "comprising," and "having," and any variations thereof, are intended to cover a non-exclusive inclusion, such that a process, method, system, article, or apparatus that comprises a list of steps or elements is not necessarily limited to those steps or elements expressly listed but may include other steps or elements not expressly listed or inherent to such process, method, article, or apparatus.
The invention is described in further detail below with reference to the attached drawing figures:
the invention provides a dielectric film of a GEMA-MMA copolymer and a preparation method thereof, wherein Guaiacol (GA) is used as a raw material to prepare guaiacol methacrylate (GEMA) through esterification reaction, and then the guaiacol methacrylate-methyl methacrylate copolymer dielectric film (GEMA-MMA copolymer dielectric film) with different proportions is prepared through polymerization with Methyl Methacrylate (MMA) in different molar proportions, and the electric breakdown strength and the energy storage performance of the GEMA-MMA copolymer dielectric film with different proportions are explored.
A preparation method of a GEMA-MMA copolymer dielectric film specifically comprises the following steps:
(1) To a three-necked flask, 24.8g of GA, 0.35g of DMAP in a molar percentage of 2mol% and 15.4g of methacrylic anhydride were added, the flask was sealed and purged with argon for 1 hour, and then the flask was placed in a silicone oil bath at 45℃and mechanically stirred for 24 hours. The mixture obtained by the reaction is then brought to normal temperature and is treated with dichloromethaneAlkane dilution followed by sequential saturation with NaHCO 3 Aqueous solution, 1mol/L NaOH aqueous solution, 0.5mol/L NaOH aqueous solution, 1.0mol/L HCl aqueous solution and deionized water. Finally, freeze-drying to obtain the GEMA.
(2) Dissolving 0.58g of GEMA and 1.5-3 g of MMA in DMF, adding 0.008-0.01 g of AIBN, sealing a small bottle, introducing argon for 1h, magnetically stirring, placing the mixed solution in methanol for precipitation after 12h, heating at 80 ℃ for 12h, and drying the solvent to obtain the GEMA-MMA copolymer dielectric film.
Example 1
A preparation method of a GEMA-MMA copolymer dielectric film specifically comprises the following steps:
(1) To a three-necked flask, 24.8g of GA, 0.35g of DMAP in a molar percentage of 2mol% and 15.4g of methacrylic anhydride were added, the flask was sealed and purged with argon for 1 hour, and then the flask was placed in a silicone oil bath at 45℃and mechanically stirred for 24 hours. The reaction mixture was then brought to ambient temperature and diluted with dichloromethane, followed by successive addition of saturated NaHCO 3 Aqueous solution, 1mol/L NaOH aqueous solution, 0.5mol/L NaOH aqueous solution, 1.0mol/L HCl aqueous solution and deionized water. Finally, freeze-drying to obtain the GEMA.
(2) Dissolving 0.58g of GEMA and 3g of MMA in DMF, adding 0.01g of AIBN, sealing a small bottle, introducing argon for 1h, magnetically stirring, precipitating the mixed solution in methanol after 12h, heating at 80 ℃ for 12h, drying the film, and separating the film in deionized water to obtain the GEMA-MMA copolymer dielectric film. The dielectric film of the GEMA-MMA copolymer has a thickness of 5 μm, the maximum electric breakdown strength of 775MV/m, and the energy storage density of the film of 8.4J/cm when the electric field strength is 550MV/m 3 The energy efficiency can reach 88 percent.
Example 2
A preparation method of a GEMA-MMA copolymer dielectric film specifically comprises the following steps:
(1) Into a three-necked flask, 24.8g of GA, 0.35g of DMAP having a mole percentage of 2mol% and 15.4g of methacrylic anhydride were charged, and the flask was sealed and purged with argon for 1 hourThe flask was placed in a silicone oil bath at 45 ℃ and mechanically stirred for 24h. The reaction mixture was then brought to ambient temperature and diluted with dichloromethane, followed by successive addition of saturated NaHCO 3 Aqueous solution, 1mol/L NaOH aqueous solution, 0.5mol/L NaOH aqueous solution, 1.0mol/L HCl aqueous solution and deionized water. Finally, freeze-drying to obtain the GEMA.
(2) Dissolving 0.58g of GEMA and 2.7g of MMA in DMF, adding 0.01g of AIBN, sealing a small bottle, introducing argon for 1h, magnetically stirring, precipitating the mixed solution in methanol after 12h, heating at 80 ℃ for 12h, drying the film, and separating the film in deionized water to obtain the GEMA-MMA copolymer dielectric film. The dielectric film of the GEMA-MMA copolymer has a thickness of 9 μm, the maximum electric breakdown strength can reach 911.2MV/m, and when the electric field strength is 550MV/m, the energy storage density of the film can reach 9.0J/cm 3 The energy efficiency can reach 92 percent.
Referring to FIG. 3, dielectric films of GEMA-MMA copolymers of the invention in different molar ratios 1 HNMR spectrum schematic; as can be seen from the figure, by 1 H NMR determines the chemical structure of the GEMA-MMA copolymer dielectric film, as shown in the figure, the nuclear magnetic peak of δ=0.8-1.9 ppm represents the hydrogen atoms on the methyl and methylene groups of the main chain and side chains on the GEMA-MMA copolymer dielectric film; the nuclear magnetic peak of delta=3.6-3.9 ppm represents a hydrogen atom on the GEMA and MMA methoxy groups on the GEMA-MMA copolymer dielectric film, and the nuclear magnetic peak of delta=6.94-7.3 ppm corresponds to a hydrogen atom on a benzene ring, which shows that the GEMA and MMA are successfully copolymerized in the reaction, and the GEMA-MMA copolymer dielectric film is successfully prepared.
Referring to FIG. 4, there is shown a schematic FT-IR spectrum of GEMA-MMA according to the invention in different proportions; wherein the molar ratio of GEMA to MMA was 1:6 for the dielectric film of the GEMA-MMA copolymer prepared in example 5 of the present invention, the molar ratio of GEMA to MMA was 1:7 for the dielectric film of the GEMA-MMA copolymer prepared in example 4 of the present invention, the molar ratio of GEMA to MMA was 1:8 for the dielectric film of the GEMA-MMA copolymer prepared in example 3 of the present invention, the molar ratio of GEMA to MMA was 1:9 for the dielectric film of the GEMA-MMA copolymer prepared in example 2 of the present invention, and the molar ratio of GEMA to MMA was 1:10 for the dielectric film of the GEMA-MMA copolymer prepared in example 1 of the present inventionAs can be seen from the figure, 1640cm of the dielectric film of the GEMA-MMA copolymer -1 The absorption peak at olefin c=c disappeared at 1607cm -1 The benzene ring unsaturated c=c absorption peak appears and is at 3075cm -1 C-H stretching vibration absorption peaks of benzene rings appear; 1750cm -1 The ester group absorption peak is also shown to indicate successful copolymerization of GEMA with MMA and successful preparation of GEMA-MMA copolymer dielectric film in this reaction.
Referring to FIG. 5, there is shown a schematic diagram of electric displacement-electric field (D-E) curve of a dielectric film of GEMA-MMA copolymer (GEMA: MMA molar ratio of 1:9) prepared in example 2 of the present invention; as can be seen from the figure, the external electric field strength is applied starting from 100MV/m and gradually increasing with the amplitude of every 50MV/m until the film breaks down. In the first quadrant, the highest point on the electric hysteresis loop gradually rises along with the increase of the electric field intensity, and the area enclosed by the electric hysteresis loop and the coordinate axis is also larger and larger, which shows that the energy loss is also more serious along with the increase of the electric field intensity, and the polarization intensity of the polymer film is increased. GEMA-MMA copolymer dielectric film with energy storage density of 9.0J/cm under electric field intensity of 550MV/m 3 。
Example 3
A preparation method of a GEMA-MMA copolymer dielectric film specifically comprises the following steps:
(1) To a three-necked flask, 24.8g of GA, 0.35g of DMAP in a molar percentage of 2mol% and 15.4g of methacrylic anhydride were added, the flask was sealed and purged with argon for 1 hour, and then the flask was placed in a silicone oil bath at 45℃and mechanically stirred for 24 hours. The reaction mixture was then brought to ambient temperature and diluted with dichloromethane, followed by successive addition of saturated NaHCO 3 Aqueous solution, 1mol/L NaOH aqueous solution, 0.5mol/L NaOH aqueous solution, 1.0mol/L HCl aqueous solution and deionized water. Finally, freeze-drying to obtain the GEMA.
(2) Dissolving 0.58g of GEMA and 2.4g of MMA in DMF, adding 0.009g of AIBN, sealing the vial and introducing argon for 1h, magnetically stirring, precipitating the mixed solution in methanol after 12h, heating at 80deg.C for 12h, drying the film and subjecting it to film in deionized waterAnd (5) separating to obtain the GEMA-MMA copolymer dielectric film. The dielectric film of the GEMA-MMA copolymer has a thickness of 10 μm, the maximum electric breakdown strength can reach 762.3MV/m, and when the electric field strength is 550MV/m, the energy storage density of the film can reach 8.7J/cm 3 The energy efficiency can reach 91 percent.
Example 4
A preparation method of a GEMA-MMA copolymer dielectric film specifically comprises the following steps:
(1) To a three-necked flask, 24.8g of GA, 0.35g of DMAP in a molar percentage of 2mol% and 15.4g of methacrylic anhydride were added, the flask was sealed and purged with argon for 1 hour, and then the flask was placed in a silicone oil bath at 45℃and mechanically stirred for 24 hours. The reaction mixture was then brought to ambient temperature and diluted with dichloromethane, followed by successive addition of saturated NaHCO 3 Aqueous solution, 1mol/L NaOH aqueous solution, 0.5mol/L NaOH aqueous solution, 1.0mol/L HCl aqueous solution and deionized water. Finally, freeze-drying to obtain the GEMA.
(2) Dissolving 0.58g of GEMA and 2.1g of MMA in DMF, adding 0.008g of AIBN, sealing a small bottle, introducing argon for 1h, magnetically stirring, precipitating the mixed solution in methanol after 12h, heating at 80 ℃ for 12h, drying the film, and separating the film in deionized water to obtain the GEMA-MMA copolymer dielectric film. The dielectric film of the GEMA-MMA copolymer has a thickness of 15 μm, the maximum electric breakdown strength of 650.5MV/m, and the energy storage density of the film of 8.1J/cm when the electric field strength is 550MV/m 3 The energy efficiency can reach 88.5%.
Example 5
A preparation method of a GEMA-MMA copolymer dielectric film specifically comprises the following steps:
(1) To a three-necked flask, 24.8g of GA, 0.35g of DMAP in a molar percentage of 2mol% and 15.4g of methacrylic anhydride were added, the flask was sealed and purged with argon for 1 hour, and then the flask was placed in a silicone oil bath at 45℃and mechanically stirred for 24 hours. The reaction mixture was then brought to ambient temperature and diluted with dichloromethane, followed by successive addition of saturated NaHCO 3 Aqueous solution, 1mol/L NaOH aqueous solution, 0.5mol/L NaOH aqueous solutionThe solution, 1.0mol/L HCl aqueous solution and deionized water were washed. Finally, freeze-drying to obtain the GEMA.
(2) Dissolving 0.58g of GEMA and 1.8g of MMA in DMF, adding 0.007g of AIBN, sealing a small bottle, introducing argon for 1h, magnetically stirring, standing the mixed solution in methanol for precipitation after 12h, heating at 80 ℃ for 12h, drying the film, and separating the film in deionized water to obtain the GEMA-MMA copolymer dielectric film. The dielectric film of the GEMA-MMA copolymer has the thickness of 11 mu m, the maximum electric breakdown strength of 638.6MV/m, and the energy storage density of the film of 8.0J/cm when the electric field strength is 550MV/m 3 The energy efficiency can reach 87.5%.
Comparative example 1
3g of MMA was dissolved in DMF, and 0.009g of AIBN was added, the vial was sealed and subjected to magnetic stirring after 1h of argon introduction, the mixed solution was precipitated in methanol after 12h, then heated at 80℃for 12h, after which the film was dried and detached from the film in deionized water, to give a pure PMMA film. The maximum electric breakdown strength of the film can reach 668.2MV/m, and when the electric field strength is 550MV/m, the energy storage density of the film can reach 6.8J/cm 3 The energy efficiency can reach 83%.
The above is only for illustrating the technical idea of the present invention, and the protection scope of the present invention is not limited by this, and any modification made on the basis of the technical scheme according to the technical idea of the present invention falls within the protection scope of the claims of the present invention.

Claims (10)

1. A method for preparing a dielectric film of a GEMA-MMA copolymer, comprising the steps of:
1) Mixing guaiacol, methacrylic anhydride and an esterifying agent uniformly, reacting in an inert atmosphere, cooling to room temperature, diluting with dichloromethane, washing, and freeze-drying to obtain GEMA;
2) Dissolving methyl methacrylate and GEMA prepared in the step 1) in DMF, adding an initiator, reacting in an inert atmosphere, purifying, heating and drying to obtain the GEMA-MMA copolymer dielectric film.
2. The method for producing a dielectric film of GEMA-MMA copolymer according to claim 1, wherein in step 2), the molar ratio of GEMA to methyl methacrylate is 1 (6-10).
3. The method for producing a dielectric film of a GEMA-MMA copolymer according to claim 1, wherein in the step 2), the inert atmosphere is argon, the reaction temperature is 80℃and the reaction time is 12 hours.
4. The method for producing a dielectric film of a GEMA-MMA copolymer as claimed in claim 1, wherein in the step 2), purification is performed by methanol precipitation, and heating is performed at 80 ℃ for 12 hours.
5. The method for producing a dielectric film of GEMA-MMA copolymer according to claim 1, wherein in step 1), guaiacol: the molar ratio of methacrylic anhydride is: 2:2:1.
6. The method for producing a dielectric film of a GEMA-MMA copolymer according to claim 1, wherein in the step 1), the esterifying agent is DMAP, and the mole percentage of the DMAP is 2mol%.
7. The method for producing a dielectric film of a GEMA-MMA copolymer according to claim 1, wherein in the step 1), the inert atmosphere is argon, and the reaction time is 24 hours.
8. The method for producing a dielectric film of GEMA-MMA copolymer as claimed in claim 1, wherein in step 1), the washing conditions are: sequentially with saturated NaHCO 3 The aqueous solution, 1mol/L NaOH aqueous solution, 0.5mol/L NaOH aqueous solution, 1.0mol/L HCl aqueous solution and deionized water were washed.
9. GEMA-MMA copolymer dielectric film prepared by the preparation method of any one of claims 1 to 8Characterized in that the dielectric film of the GEMA-MMA copolymer has the thickness of 5-15 mu m, the electric breakdown strength of 911.2-638.6 MV/m and the energy storage density of 8.0-9.0J/cm 3 The energy efficiency is 87.5% -92%.
10. Use of a GEMA-MMA copolymer dielectric film of claim 9 for the preparation of metallized film capacitors.
CN202211718111.7A 2022-12-29 2022-12-29 GEMA-MMA copolymer dielectric film and preparation method and application thereof Pending CN116003846A (en)

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