CN115536880A - Polyarylether ketone-based dielectric film containing rigid ring structure and preparation method and application thereof - Google Patents
Polyarylether ketone-based dielectric film containing rigid ring structure and preparation method and application thereof Download PDFInfo
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- 229920006260 polyaryletherketone Polymers 0.000 title claims abstract description 71
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000004146 energy storage Methods 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 22
- 230000015556 catabolic process Effects 0.000 claims abstract description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 37
- 239000000178 monomer Substances 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 125000004122 cyclic group Chemical group 0.000 claims description 19
- 239000000243 solution Substances 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- 238000001035 drying Methods 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 13
- 239000011259 mixed solution Substances 0.000 claims description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 11
- 239000003990 capacitor Substances 0.000 claims description 8
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- 239000002994 raw material Substances 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- FKVQQQMZAGNIRP-UHFFFAOYSA-N 2-[2-(1h-benzimidazol-2-yl)pyridin-3-yl]-1h-benzimidazole Chemical compound C1=CC=C2NC(C3=NC=CC=C3C=3NC4=CC=CC=C4N=3)=NC2=C1 FKVQQQMZAGNIRP-UHFFFAOYSA-N 0.000 claims description 6
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- NSTFTBDDHJZGLB-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)-2-adamantyl]phenol Chemical compound C1=CC(O)=CC=C1C1C(C=2C=CC(O)=CC=2)(C2)CC3CC2CC1C3 NSTFTBDDHJZGLB-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- -1 methacryloxypropyl Chemical group 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- LSQARZALBDFYQZ-UHFFFAOYSA-N 4,4'-difluorobenzophenone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 LSQARZALBDFYQZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000005357 flat glass Substances 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 238000006068 polycondensation reaction Methods 0.000 claims description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
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- 238000000137 annealing Methods 0.000 abstract description 6
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- 239000010408 film Substances 0.000 description 52
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 150000001993 dienes Chemical class 0.000 description 5
- 238000007599 discharging Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000011127 biaxially oriented polypropylene Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910017053 inorganic salt Inorganic materials 0.000 description 4
- 229910001867 inorganic solvent Inorganic materials 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
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- 238000010586 diagram Methods 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 238000000944 Soxhlet extraction Methods 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 239000003989 dielectric material Substances 0.000 description 2
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 239000004696 Poly ether ether ketone Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
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- 239000002131 composite material Substances 0.000 description 1
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- 125000000524 functional group Chemical group 0.000 description 1
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- 229920002530 polyetherether ketone Polymers 0.000 description 1
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
- C08G65/4031—(I) or (II) containing nitrogen
- C08G65/4037—(I) or (II) containing nitrogen in ring structure, e.g. pyridine group
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
- C08G65/4068—(I) or (II) containing elements not covered by groups C08G65/4018 - C08G65/4056
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4093—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group characterised by the process or apparatus used
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- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/08—Heat treatment
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- C08J2371/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
- C08J2371/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08J2371/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08J2371/12—Polyphenylene oxides
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Abstract
The invention provides a polyaryletherketone-based dielectric film containing a rigid ring structure, and a preparation method and application thereof. The method is a method for preparing a dielectric film by introducing a rigid ring structure into a molecular main chain of polyaryletherketone in the synthesis process of the polyaryletherketone to obtain a novel polyaryletherketone-based copolymer. The introduction of the rigid annular structure not only improves the heat resistance of the copolymer film, but also effectively reduces leakage current, and improves breakdown field strength and energy storage density. The copolymer film can be conveniently prepared by adopting a solution casting method, and the high-temperature-resistant and high-energy-storage dielectric film can be obtained after high-temperature annealing treatment. The stable use temperature of the dielectric film in the invention is not lower than 150 ℃, and under high temperature,the breakdown strength of the material reaches 500-750MV/m, and the energy storage density reaches 5.0-10.0J/cm 3 The energy release efficiency is not less than 90%. Meanwhile, 5000 times of capacitance charge and discharge tests show that the releasable efficiency is not lower than 90%, and key indexes are superior to those of the existing high-temperature-resistant commercial engineering film.
Description
Technical Field
The invention relates to the technical field of organic dielectric film synthesis, in particular to a polyaryletherketone-based dielectric film containing a rigid ring structure, and a preparation method and application thereof.
Background
In the field of military and civil high-end equipment such as extra-high voltage, high-speed rail crossing, all-electric ship aircraft, electromagnetic energy equipment and the like, the pulse capacitor with the characteristics of high temperature resistance and high energy storage density is indispensable and important. At present, biaxially oriented polypropylene (BOPP) has the advantages of high voltage resistance (700 MV/m), low loss (tan δ ≈ 0.02%), self-healing, low cost, and the like, and is widely applied to various thin film capacitors for power systems and electronic devices. However, the BOPP has a low temperature of less than 85 ℃ for long-term use, and when the temperature rises to above 105 ℃, the leakage conduction current increases and the loss increases rapidly, and particularly under the action of high temperature and high electric field, the internal conductivity of the dielectric material increases exponentially and the leakage conduction current increases rapidly, which not only reduces the energy storage density and the charging and discharging efficiency, but also causes the electrical insulation failure of the capacitor due to the thermal instability state in the capacitor, and the service life is shortened greatly.
For example, a power inverter can convert dc power provided by a battery into ac power required to drive a traction motor, which is one of the important electronic components of an electric vehicle, and the key components in the inverter include a pulse capacitor. BOPP is currently the best commercial dielectric film, but can only operate at temperatures below 105 ℃. In the inverter, the working temperature is higher than 140 ℃, so a secondary cooling system with the temperature set to 65 ℃ needs to be introduced into the inverter to ensure the long-term stable operation of the inverter. This not only brings extra weight and volume for the design of electric power system, is unfavorable for the benefit of electric automobile's the cost reduction moreover. Therefore, there is an urgent need in the market to develop a new high-temperature-resistant and high-energy-storage dielectric thin film to replace BOPP, thereby achieving the objectives of small volume and low cost.
Disclosure of Invention
The invention provides a novel high-temperature-resistant and high-energy-storage PAEKs (polyether-ether-ketone-based dielectric film) containing rigid ring structures, a preparation method and application thereof, and the specific technical scheme is as follows:
the invention provides a preparation method of a polyaryletherketone-based dielectric film containing a rigid ring structure, which comprises the steps of firstly preparing a rigid ring structure monomer; then taking the rigid ring structure monomer as a raw material to prepare polyaryletherketone containing a rigid ring structure; and finally, preparing the polyaryletherketone-based dielectric film containing the rigid ring structure by taking polyaryletherketone containing the rigid ring structure as a raw material.
Preferably, the method comprises the following specific steps: 1) Preparing a rigid cyclic structure monomer, wherein the rigid cyclic structure monomer is one or more of bis (2-benzimidazolyl) pyridine, bis (4-hydroxyphenyl) adamantane and methacryloxypropyl POSS; 2) Preparing polyaryletherketone containing a rigid ring structure, taking 4,4' -difluorobenzophenone, diallyl bisphenol A and the rigid ring structure monomer as raw materials, adding a solvent, a water removing agent and a salt forming agent, and mixing to obtain a solution; carrying out the following reactions under the protection of nitrogen, carrying out the reactions through three-stage heating processes, carrying out prepolymerization salification reaction, heating toluene for reflux to remove water, and finally carrying out polycondensation reaction at high temperature to obtain a crude product; pouring the crude product into an aqueous solution of hydrochloric acid, crushing, washing with hot water and ethanol respectively, and drying to obtain the polyaryletherketone containing the rigid ring structure; 3) Preparing cross-linked polyaryletherketone, taking the polyaryletherketone group containing the rigid ring structure, stirring in a DMAc solution to obtain a stable and uniform mixed solution, coating the mixed solution on a flat glass plate, and drying the solvent at 70 ℃ to form a film; then the film is put into a baking oven and treated for 6 hours at the high temperature of 180-200 ℃ to obtain the polyaryletherketone-based dielectric film containing the rigid ring structure.
Preferably, in the step (2), the molar ratio of the diallylbisphenol a to the rigid cyclic monomer is (9.
Preferably, in the step (2), the ratio of the mass of the rigid cyclic monomer to the mass of the solvent is 5% to 30%.
Preferably, in the step (3), the solid content of the rigid cyclic structure monomer in the mixed solution is 5 to 30 percent
Preferably, in the step (2), the solvent is one or more of N, N '-dimethylformamide, N' -dimethylacetamide and N-methylpyrrolidone; the water removing agent is toluene; the salt forming agent is anhydrous potassium carbonate.
Preferably, the thickness of the high-temperature-resistant dielectric thin film is 5-12 μm; the high-temperature resistant dielectric film has a dielectric constant of 3.0-5.0.
Preferably, the breakdown strength of the high-temperature-resistant dielectric film at 150 ℃ is 500 MV/m-750 MV/m, and the energy storage density is 5.0J/cm 3 ～10.0J/cm 3 The energy storage efficiency is not lower than 90%.
The invention also provides a polyaryletherketone-based dielectric film containing a rigid ring structure, which is prepared by the preparation method of the polyaryletherketone-based dielectric film containing a rigid ring structure.
The invention also provides the application of the polyaryletherketone-based dielectric film containing the rigid ring structure in the fields of capacitors, electric automobile inverters, electric power flexible transmission systems, new energy power generation and underground oil and gas exploration.
Compared with the prior art, the technical scheme provided by the invention at least has the following advantages:
the invention provides a polyaryletherketone-based dielectric film containing a rigid ring structure, and a preparation method and application thereof. Wherein, the introduction of rigid cyclic structure is not only beneficial to improving the heat resistance of the copolymer film, but also beneficial to improving the heat resistance of the copolymer filmThe leakage current can be effectively reduced, and the breakdown field strength and the energy storage density of the composite material can be improved. The copolymer film can be conveniently prepared by adopting a solution casting method, and the high-temperature-resistant and high-energy-storage dielectric film can be obtained after high-temperature annealing treatment. The dielectric film prepared by the invention has the stable use temperature of not less than 150 ℃, the breakdown strength of 500-750MV/m and the energy storage density of 5.0J/cm at high temperature 3 ～10.0J/cm 3 The energy release efficiency is not less than 90%. Meanwhile, through 5000 times of capacitance charge and discharge tests, the releasable efficiency is not lower than 90%, key indexes are superior to those of the existing high-temperature-resistant commercial engineering film, and the film has the advantages of high temperature resistance, high energy storage, easiness in processing and the like.
Drawings
One or more embodiments are illustrated by corresponding figures in the drawings, which are not to be construed as limiting the embodiments, unless expressly stated otherwise, and the drawings are not to scale.
FIG. 1 is a schematic diagram of the synthesis route of the polyaryletherketone-based dielectric film containing rigid ring structure prepared in example 1 of the present invention;
FIG. 2 is a graph showing the dielectric constant and dielectric loss as a function of frequency for the polyaryletherketone based dielectric film containing rigid ring structures prepared in example 1 of the present invention;
FIG. 3 is a Weibull plot of the breakdown strength at 150 ℃ of the polyaryletherketone-based dielectric film containing rigid ring structures prepared in example 1 of the present invention;
FIG. 4 is a schematic diagram of the D-E loop at 150 ℃ of 0-650MV/m for a polyaryletherketone based dielectric film containing a rigid ring structure prepared in example 1 of the present invention;
FIG. 5 is a graph showing the comparison between the energy storage density and the energy storage efficiency at 150 ℃ of the polyaryletherketone-based dielectric film containing rigid cyclic structures prepared in example 1 of the present invention.
FIG. 6 is a schematic diagram showing the energy storage density and release efficiency of the polyaryletherketone-based dielectric thin film containing rigid ring structures prepared in example 1 of the present invention after 5000 cycles of recycling.
Detailed Description
The existing commercialized high-temperature-resistant polymer material has greatly reduced energy storage performance, especially energy release efficiency, and greatly reduced working stability and service cycle of a capacitor at high temperature due to sudden drop of resistivity and increase of leakage conduction current.
The inventors have found that Polyaryletherketones (PAEKs) are an important class of high performance aromatic polymers with excellent thermal stability, mechanical properties and chemical resistance. PAEKs can be obtained by polycondensation of a variety of polyfunctional monomers by nucleophilic reactions. The molecular structures of the compounds are highly adjustable and easy to functionalize, and can realize wide adjustment of temperature resistance, polarity and flexibility. By a chemical synthesis modification method, a high temperature resistant and charge transport control functional group or structure is introduced into a main chain or a side chain of the PAEKs polymer, and the PAEKs polymer with high temperature resistance and high energy storage property is hopefully prepared.
The invention provides a preparation method of a polyaryletherketone-based dielectric film containing a rigid ring structure, which comprises the following steps:
rigid cyclic monomers are prepared, including but not limited to bis (2-benzimidazolyl) pyridine, bis (4-hydroxyphenyl) adamantane, methacryloxypropyl POSS, and norbornene. The monomer is washed to neutrality in dilute NaOH solution, HCl solution or chloroform solution. Suction filtration and recrystallization were carried out. The product was dried under vacuum at 50 ℃ to give a purified monomer containing a rigid cyclic structure.
Diallyl bisphenol A, 4' -difluorobenzophenone and the rigid structure-containing monomer are used as raw materials, the molar ratio of the diallyl bisphenol A to the rigid structure-containing monomer is 9.
Wherein, the reaction temperature is three-stage, and prepolymerization is carried out at 130-140 ℃; secondly, heating to 140-150 ℃ to perform azeotropic dehydration on toluene, and simultaneously performing salt forming reaction; finally reacting for 6 hours at 180-200 ℃ to obtain a crude product.
And the post-treatment is to pour the crude product into an aqueous solution of hydrochloric acid, crush the crude product, wash the crude product by using hot water and ethanol respectively, and finally obtain the crosslinkable polyaryletherketone containing the rigid ring structure after drying.
Weighing 0.1-1 g of the prepared novel polyaryletherketone, and stirring for more than 4 hours in 5-50 mL of DMAc solution to obtain a stable and uniform mixed solution.
The mixed solution is coated on a flat glass plate, and the solvent is dried at 70 ℃ to form a film. And then putting the crosslinkable polyaryletherketone film containing the rigid annular structure into an oven, and carrying out high-temperature treatment for 6h at 180 ℃ to obtain the crosslinked high-temperature-resistant dielectric film. In particular, the introduced rigid structure can improve the temperature resistance of the polyaryletherketone group, and the crosslinking structure can improve the toughness of the film and the compressive strength of the film.
The present invention will be described in detail with reference to the following embodiments.
the first step is as follows: in N 2 Under the condition, polyphosphoric acid is used as a condensing agent and a solvent, o-phenylenediamine and dipicolinic acid are used as monomers, the molar ratio of the two is 2. And washing the reaction product in a NaOH solution with the mass fraction of 15% to be neutral. Suction filtration and recrystallization with ethanol. And drying the product at 50 ℃ in vacuum to obtain the purified bis (2-benzimidazolyl) pyridine monomer.
The second step: in a 250mL three-necked flask to which a nitrogen port through which a thermometer was inserted, a stirring paddle and a water-carrying device were connected, diene bisphenol A (6.618g, 0.02mol), 4' -difluorobenzophenone (5.455g, 0.025mol) and bis (2-benzimidazolyl) pyridine (1.555g, 0.005mol) were charged in this order, followed by addition of anhydrous potassium carbonate (7.60g, 0.055mol).
The third step: adding 40-50 mL of sulfolane solvent and 10-20 mL of toluene as water-carrying agent into the system, introducing nitrogen gas, and heating under stirring until the toluene carries water to reflux, thereby ensuring that the water in the system is removed.
The fourth step: by means of the staged heating method, the system is heated to 130-140 deg.c, 140-150 deg.c and 180-200 deg.c successively for reaction. And after the reaction is finished, discharging the mixture solution into a hydrochloric acid aqueous solution, crushing by using a powder machine, washing materials for multiple times by adopting boiling distilled water and ethanol, and removing residual inorganic salt and solvent. Drying in an oven to obtain the polyaryletherketone polymer containing rigid groups.
The fifth step: a20 mL sample bottle was charged with 200mg of a polyaryletherketone polymer containing a rigid group, dissolved by adding 10mLN, N' -dimethylacetamide, and stirred at room temperature.
And a sixth step: and (3) coating the mixed solution on a glass sheet in a casting manner, and drying the solvent at 70 ℃ to form a film.
The seventh step: and (3) putting the dielectric film prepared in the sixth step into an oven at 180 ℃ for annealing for 6h to obtain the crosslinked polyarylether ketone-based dielectric film containing the rigid ring structure.
Eighth step: the prepared dielectric film has the energy storage density of 7.2J/cm under the conditions that the test temperature is 150 ℃, the dielectric constant is 4.3 and the breakdown strength is 600MV/m 3 The energy storage efficiency was 87%.
the first step is as follows: under the protection of nitrogen, 1, 3-dibromodiamantane and phenol are used as monomers, aluminum trichloride is used as a catalyst, and the molar ratio of the monomer to the phenol is 5:20:1, adding the mixture into a round-bottom flask, and reacting for 12-16 h at 80 ℃. The hydrogen bromide gas generated in the reaction process is absorbed by sodium hydroxide solution. After the reaction is finished, excessive aluminum trichloride and phenol are washed away by hot water, and soxhlet extraction is carried out by taking methanol as a solvent after vacuum drying. Recrystallizing the concentrated solution obtained by the Soxhlet extraction to obtain a white flaky crystal product, namely the bis (4-hydroxyphenyl) adamantane.
The second step is that: in a 250mL three-necked flask to which a nitrogen port through which a thermometer was inserted, a stirring paddle and a water carrying device were connected, diene bisphenol A (4.566 g, 0.02mol), 4' -difluorobenzophenone (5.455g, 0.025mol), bis (4-hydroxyphenyl) adamantane (1.61g, 0.005mol) and anhydrous potassium carbonate (7.60g, 0.055mol) were sequentially charged.
The third step: adding 40-50 mL of sulfolane solvent and 20-30 mL of toluene as water-carrying agent into the system, introducing nitrogen gas, and heating under stirring until the toluene carries water to reflux, thereby ensuring that the water in the system is removed.
The fourth step: the system is heated to 130-140 ℃, 150-160 ℃ and 180-200 ℃ in sequence by a stage heating method for reaction. And after the reaction is finished, discharging the mixture solution into a hydrochloric acid aqueous solution, crushing by using a powder machine, washing materials for multiple times by adopting boiling distilled water and ethanol, and removing residual inorganic salt and solvent. Drying in an oven to obtain the polyaryletherketone polymer containing rigid groups.
The fifth step: a20 mL sample bottle was charged with 200mg of a polyaryletherketone polymer containing a rigid group, dissolved in 10mL of N' -dimethylacetamide, and stirred at room temperature.
And a sixth step: and (3) coating the mixed solution on a glass sheet in a casting manner, and drying the solvent at 70 ℃ to form a film.
The seventh step: and (3) putting the dielectric film prepared in the sixth step into an oven at the temperature of 180-200 ℃ for annealing for 6 hours to obtain the crosslinked polyaryletherketone-based dielectric film containing the rigid ring structure.
the first step is as follows: 40-50 mL of absolute ethanol and 0.1mol of p-benzoquinone are added into an erlenmeyer flask, and the erlenmeyer flask is placed into an ice-water bath. After ten minutes, 0.11 to 0.13mol of cyclopentadiene is added and stirred for fifteen minutes. After standing at room temperature for 1h, the solution turned from cloudy to clear and orange-yellow with a lot of yellowish precipitate. Ethanol was distilled off under reduced pressure at low temperature to give a pale yellow solid. Recrystallizing with petroleum ether to obtain light yellow needle crystal. To the product was added 100mL of ethyl acetate and 20g of basic alumina, and stirred in a water bath at 25 ℃ for 12h. The alkaline alumina was removed by filtration and the ethyl acetate was removed by rotary evaporation to give a red viscous liquid. Chloroform was added to the solution to wash it until a white solid norbornene-containing hydroquinone monomer was obtained.
The second step is that: in a 250mL three-necked flask to which a nitrogen port through which a thermometer was inserted, a stirring paddle and a water carrying device were connected, diene bisphenol A (4.566 g, 0.02mol), 4' -difluorobenzophenone (5.455g, 0.025mol), and a norbornene-containing hydroquinone monomer (1.555g, 0.005mol) were charged in this order, followed by addition of anhydrous potassium carbonate (7.60g, 0.055mol).
The third step: adding 40-50 mL of solvent DMAc and 10-20 mL of toluene as a water-carrying agent into the system, introducing nitrogen, and heating under stirring until the toluene carries water to reflux, thereby ensuring that the water in the system is removed.
The fourth step: by means of the staged heating method, the system is heated to 130-140 deg.c, 140-160 deg.c and 180-200 deg.c successively for reaction. And after the reaction is finished, discharging the mixture solution into a hydrochloric acid aqueous solution, crushing by using a powder machine, washing materials for multiple times by adopting boiling distilled water and ethanol, and removing residual inorganic salt and solvent. Drying in an oven to obtain the polyaryletherketone polymer containing rigid groups.
The fifth step: a20 mL sample bottle was charged with 200mg of a polyaryletherketone polymer containing a rigid group, dissolved in 10mL of N' -dimethylacetamide, and stirred at room temperature.
And a sixth step: and (3) coating the mixed solution on a glass sheet in a casting manner, and drying the solvent at 70 ℃ to form a film.
The seventh step: and (3) putting the dielectric film prepared in the sixth step into an oven at 180 ℃ for annealing for 6h to obtain the crosslinked polyarylether ketone-based dielectric film containing the rigid ring structure.
the first step is as follows: in a 250mL three-necked flask having a nitrogen port through which a thermometer was inserted, a stirring paddle and a water-carrying device connected thereto, diene bisphenol A (4.566 g, 0.02mol) and 4,4' -difluorobenzophenone (5.455g, 0.025mol) were charged in this order, followed by anhydrous potassium carbonate (7.60g, 0.055mol) was added thereto.
The second step: adding 40-50 mL of sulfolane solvent and 10-20 mL of toluene as water-carrying agent into the system, introducing nitrogen gas, and heating under stirring until the toluene carries water to reflux, thereby ensuring that the water in the system is removed.
The third step: by means of the staged heating method, the system is heated to 130-140 deg.c, 140-150 deg.c and 180-200 deg.c successively for reaction. And after the reaction is finished, discharging the mixture solution into a hydrochloric acid aqueous solution, crushing by using a powder machine, washing materials for multiple times by adopting boiling distilled water and ethanol, and removing residual inorganic salt and solvent. Drying in an oven to obtain the polyaryletherketone polymer with double bonds.
The fourth step: a20 mL sample bottle was charged with 200mg of a polyaryletherketone polymer containing a rigid group, dissolved in 10mL of N' -dimethylacetamide, and stirred at room temperature.
The fifth step: and adding 0.05mol of methacryloxypropyl POSS into the solution obtained in the fourth step, adding a small amount of benzoyl peroxide, and reacting for 10-12 hours to finish the reaction.
And a sixth step: and (3) coating the obtained mixed solution on a glass sheet in a casting manner, and drying the solvent at 70 ℃ to form a film.
The seventh step: and putting the dielectric film prepared in the sixth step into an oven at 180 ℃ for annealing for 6h to obtain the crosslinked polyaryletherketone-based dielectric film containing the rigid ring structure.
FIG. 1 shows a synthesis scheme of polyaryletherketone polymer, and the monomers are diene bisphenol A, 4' -difluorobenzophenone and bis (2-benzimidazolyl) pyridine, including but not limited to the monomers in the scheme. FIG. 2 shows that the dielectric constant of the polymer can reach 4.0-4.5, and the dielectric loss is between 0.004-0.01. As can be seen from the analysis of FIGS. 3 to 6, the maximum polarization value of example 1 was 2.94. Mu.c/m at a test temperature of 150 ℃ and a breakdown strength of 650MV/m 2 . The high-temperature-resistant dielectric film prepared by the invention is beneficial to the improvement of the discharge energy storage density. As can be seen from the analysis of FIG. 5, the energy storage density of the refractory dielectric thin film prepared in example 1 of the present invention is 5.3 to 8.7J/cm under the conditions of the test temperature of 150 ℃ and the breakdown strength of 500 to 650MV/m 3 And the release efficiency of stored energy is 82% -91%. In addition, as shown in FIG. 6, the high temperature resistant dielectric film prepared by the invention can be recycled more than 5000 times at 150 ℃ and 250MV/m, and the efficiency is still more than 95%. The novel polyaryletherketone base material has more excellent high-temperature application, and effectively solves the problem that the internal conductivity of the dielectric material is exponentially increased due to the increase of temperature, so that the energy storage density and the charge-discharge efficiency are reduced.
It will be understood by those of ordinary skill in the art that the foregoing embodiments are specific examples for carrying out the present application, and that various changes in form and details may be made therein without departing from the spirit and scope of the present application in practice. Various changes and modifications may be effected therein by one skilled in the art without departing from the spirit and scope of the application, and it is intended that the scope of the application be limited only by the claims appended hereto.
Claims (10)
1. The preparation method of the polyaryletherketone-based dielectric film containing the rigid ring structure is characterized by firstly preparing a rigid ring structure monomer; then taking the rigid ring structure monomer as a raw material to prepare polyaryletherketone containing a rigid ring structure; and finally, preparing the polyaryletherketone-based dielectric film containing the rigid ring structure by using polyaryletherketone containing the rigid ring structure as a raw material.
2. The method of claim 1, comprising the following steps:
1) Preparing a rigid cyclic structure monomer, wherein the rigid cyclic structure monomer is one or more of bis (2-benzimidazolyl) pyridine, bis (4-hydroxyphenyl) adamantane and methacryloxypropyl POSS;
2) Preparing polyaryletherketone containing a rigid ring structure, taking 4,4' -difluorobenzophenone, diallyl bisphenol A and the rigid ring structure monomer as raw materials, adding a solvent, a water removing agent and a salt forming agent, and mixing to obtain a solution; carrying out the following reactions under the protection of nitrogen, carrying out the reactions through three-stage heating processes, carrying out prepolymerization salification reaction, heating toluene for reflux to remove water, and finally carrying out polycondensation reaction at high temperature to obtain a crude product; pouring the crude product into an aqueous solution of hydrochloric acid, crushing, washing with hot water and ethanol respectively, and drying to obtain the polyaryletherketone containing the rigid ring structure;
3) Preparing cross-linked polyaryletherketone, stirring the polyaryletherketone group containing the rigid ring structure in a DMAc solution to obtain a stable and uniform mixed solution, coating the mixed solution on a flat glass plate, and drying the solvent at 70 ℃ to form a film; then the film is put into a baking oven and treated for 6 hours at the high temperature of 180-200 ℃ to obtain the polyaryletherketone-based dielectric film containing the rigid ring structure.
3. The method of producing a rigid cyclic structure-containing polyaryletherketone-based dielectric film according to claim 2, wherein in the step (2), the molar ratio of the diallyl bisphenol A to the rigid cyclic structure monomer is (9.
4. The method for preparing a polyaryletherketone-based dielectric film containing a rigid cyclic structure as claimed in claim 2, wherein in the step (2), the mass of the rigid cyclic structure monomer in the solvent is 5% to 30%.
5. The method for preparing polyaryletherketone-based dielectric film containing rigid cyclic structure as claimed in claim 2, wherein in step (3), the solid content of rigid cyclic structure monomer in the mixed solution is 5-30%
6. The method for preparing a refractory dielectric film according to claim 2, wherein in step (2), the solvent is one or more of N, N '-dimethylformamide, N' -dimethylacetamide and N-methylpyrrolidone; the water removing agent is toluene; the salt forming agent is anhydrous potassium carbonate.
7. The method of claim 1, wherein the thickness of the high temperature resistant dielectric film is 5 μm to 12 μm; the high-temperature resistant dielectric film has a dielectric constant of 3.0-5.0.
8. The method of claim 1, wherein the polyaryletherketone-based dielectric film with rigid ring structure is preparedThe preparation method is characterized in that the breakdown strength of the high-temperature-resistant dielectric film at 150 ℃ is 500 MV/m-750 MV/m, and the energy storage density is 5.0J/cm 3 ～10.0J/cm 3 And the energy storage efficiency is not lower than 90%.
9. A polyaryletherketone based dielectric film containing a rigid cyclic structure, which is prepared by the method for preparing a polyaryletherketone based dielectric film containing a rigid cyclic structure according to any one of claims 1 to 8.
10. The polyaryletherketone based dielectric film containing rigid ring structure of claim 9, for use in capacitor, electric vehicle inverter, electric power flexible transmission system, new energy generation and downhole oil and gas exploration applications.
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