CN115253713B - Polyetherketone organic solvent nanofiltration membrane material and preparation method thereof - Google Patents
Polyetherketone organic solvent nanofiltration membrane material and preparation method thereof Download PDFInfo
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- 239000012528 membrane Substances 0.000 title claims abstract description 76
- 239000003960 organic solvent Substances 0.000 title claims abstract description 59
- 238000001728 nano-filtration Methods 0.000 title claims abstract description 52
- 229920001643 poly(ether ketone) Polymers 0.000 title claims abstract description 49
- 239000000463 material Substances 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims abstract description 26
- 229920000642 polymer Polymers 0.000 claims abstract description 49
- 238000004528 spin coating Methods 0.000 claims abstract description 34
- 238000001035 drying Methods 0.000 claims abstract description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 14
- -1 ether ketone Chemical class 0.000 claims abstract description 14
- 229920000098 polyolefin Polymers 0.000 claims abstract description 8
- 238000000108 ultra-filtration Methods 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 2
- 239000004696 Poly ether ether ketone Substances 0.000 claims description 2
- 239000004642 Polyimide Substances 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000919 ceramic Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 2
- 229920002530 polyetherether ketone Polymers 0.000 claims description 2
- 229920001721 polyimide Polymers 0.000 claims description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 229920001470 polyketone Polymers 0.000 claims 4
- 150000002576 ketones Chemical class 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract description 16
- 238000000034 method Methods 0.000 abstract description 15
- 230000008569 process Effects 0.000 abstract description 14
- 239000002904 solvent Substances 0.000 abstract description 12
- 230000004907 flux Effects 0.000 abstract description 10
- 238000009826 distribution Methods 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 4
- 238000000605 extraction Methods 0.000 abstract description 4
- 239000011148 porous material Substances 0.000 abstract description 4
- 239000012847 fine chemical Substances 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 3
- 150000001336 alkenes Chemical group 0.000 abstract description 2
- 238000003889 chemical engineering Methods 0.000 abstract description 2
- 229920005597 polymer membrane Polymers 0.000 abstract description 2
- 239000013076 target substance Substances 0.000 abstract description 2
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 238000005516 engineering process Methods 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 239000004693 Polybenzimidazole Substances 0.000 description 1
- 229920002614 Polyether block amide Polymers 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/10—Supported membranes; Membrane supports
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0002—Organic membrane manufacture
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0079—Manufacture of membranes comprising organic and inorganic components
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/02—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor characterised by their properties
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A20/00—Water conservation; Efficient water supply; Efficient water use
- Y02A20/124—Water desalination
- Y02A20/131—Reverse-osmosis
Abstract
The invention relates to the technical field of polymer membrane materials and membrane separation, in particular to a polyethenone organic solvent nanofiltration membrane material and a preparation method thereof. The polyolefin ether ketone polymer has a twisted, rigid and all-trans olefin structure, and has the characteristics of self micropores and narrow pore size distribution. And dissolving the poly (ether ketone) polymer into an organic solvent, coating the poly (ether ketone) polymer on the surface of the porous support membrane by adopting a spin coating process, and drying under specific conditions to obtain the poly (ether ketone) organic solvent nanofiltration membrane material. The membrane material has the characteristics of high flux and high precision, can resist most of organic solvents, can realize industrial separation processes such as concentration, purification, solvent exchange and the like of target substances, and has important application values in the fields such as fine chemical engineering, petrochemical engineering, synthetic pharmacy, medicine extraction and the like.
Description
Technical Field
The invention relates to the technical field of polymer membrane materials and membrane separation, in particular to a polyethenone organic solvent nanofiltration membrane material and a preparation method thereof.
Background
Currently, industrial separations are processes such as distillation, rectification, and extraction with high latent heat or complex processes. It is estimated that the energy consumption of the separation process is 10-15% of the total world energy consumption, and can be reduced by nearly 90% if membrane separation technology is used instead of the traditional separation method (Nature, 2016,532 (7600):435-437).
In the industries of petrochemical industry, fine chemical industry, drug synthesis, drug extraction, etc., organic solvents are applied in large amounts to separation processes. The organic solvent nanofiltration membrane separation technology can realize the processes of concentration, purification, solvent exchange and the like of target substances in an organic solvent, has mild operation conditions, and can avoid the inactivation of heat-sensitive substances. It can be seen that the organic solvent nanofiltration membrane separation technology is of great importance in industrial separations. The membrane material is the core of the membrane technology, and the high-performance organic solvent nanofiltration membrane can realize high-efficiency separation.
Reference is made to the chinese patent application publication No. cn20180040390. X for asymmetric membranes for nanofiltration (application publication No. CN103079685 a), which describes the phase inversion of polybenzimidazole and the addition of a cross-linking agent for cross-linking, a nanofiltration membrane is prepared which can be stably operated in a solvent.
The Chinese patent application with reference to application No. CN202010336413.2 discloses a high-performance polymer organic solvent nanofiltration membrane and a preparation method thereof (application publication No. CN 111450717A), wherein a block polyether amide polymer is dissolved in a solvent, cyclodextrin is added into the solution, the obtained solution is soaked or spin-coated on the ultrafiltration membrane, and then crosslinking is carried out, so that the composite membrane is prepared for organic solvent nanofiltration.
Due to the limitation of membrane materials, the organic solvent nanofiltration membrane prepared at present has the common problems of low permeability or/and low selection precision. In industrial separation applications, there is a problem of low separation efficiency. Therefore, development of high-performance organic solvent nanofiltration membranes is required to solve the problem, and promotion of industrial separation process upgrading is promoted. In view of the above problems, a solution is proposed below.
Disclosure of Invention
The invention aims to provide a polyethenone organic solvent nanofiltration membrane material and a preparation method thereof, and the polyethenone organic solvent nanofiltration membrane material has the characteristics of simple process, high flux and high precision, can resist most of organic solvents, and has the advantage of important application value.
The technical aim of the invention is realized by the following technical scheme:
a poly (ether ketone) organic solvent nanofiltration membrane material and a preparation method thereof comprise the following steps that S1, a poly (ether ketone) polymer solution is prepared, the poly (ether ketone) polymer is completely dissolved in an organic solvent, and the mass fraction of the poly (ether ketone) polymer is 0.1-5%, so that the poly (ether ketone) polymer solution is prepared;
s2, spin coating is carried out on the surface of the porous support film by using a polyalkene ether ketone polymer solution, wherein the spin coating comprises a first stage and a second stage, the spin coating rotating speed of the first stage is 50-1000 revolutions per minute, the spin coating time is 1-10 seconds, the spin coating rotating speed of the second stage is 500-5000 revolutions per minute, and the spin coating time is 5-60 seconds;
s3, drying the spin-coated porous support membrane, wherein the drying temperature is 15-100 ℃, the drying time is 1-60 minutes, and the polyolefin ether ketone organic solvent nanofiltration membrane material is prepared after the drying is completed.
Preferably, the organic solvent in S1 is one or more of tetrahydrofuran, dichloromethane, chloroform, N-dimethylformamide and N, N-dimethylacetamide.
Preferably, the mass fraction of the poly (ether ketone) polymer in S1 is 0.5 to 2%.
Preferably, the mass fraction of the poly (ether ketone) polymer in S1 is 1%.
Preferably, the porous support membrane in S2 is any one of polyimide, polyacrylonitrile, polyetheretherketone polymer ultrafiltration membrane, or alumina, silicon carbide, and zirconia inorganic ceramic ultrafiltration membrane.
Preferably, the spin coating rotating speed of the first stage in the S2 is 200-600 rpm, and the spin coating time is 2-5 seconds; the spin coating rotating speed of the second stage in the S2 is 1000-3000 rpm, and the spin coating time is 20-50 seconds.
Preferably, the spin-coating rotation speed in the first stage in S2 is 500 rpm, and the spin-coating time is 3 seconds; the spin-coating speed in the second stage in S2 was 2000 rpm and the spin-coating time was 40 seconds.
Preferably, the drying temperature in S3 is 20 to 60℃and the drying time is 2 to 30 minutes.
Preferably, the drying temperature in S3 is 30℃and the drying time is 5 minutes.
The structure of the poly (ether-ketone) polymer in S1 is as shown in formula (I):
in the formula (I), R1 is selected from any one of 1 to 3;
in the formula (I), R2 is selected from any one of 4 to 6;
wherein, represent the positions of the acyl alkynyl and hydroxyl functional groups.
The beneficial effects of the invention are as follows: the designed and synthesized polyolefin ether ketone polymer has rigid, twisted and all-trans olefin structure, and the prepared polymer has the characteristics of self micropores and narrow pore size distribution. The prepared polyethenoxy ether ketone organic solvent nanofiltration membrane material has the characteristics of high flux and high precision, can resist most of organic solvents, can realize industrial separation processes such as concentration, purification, solvent exchange and the like of target molecules, and has important application value in the fields such as fine chemical engineering, petrochemical engineering, synthetic pharmacy, medicine extraction and the like.
Detailed Description
Specific embodiments of the present invention are described below, but the present invention is not limited by the embodiments. All modifications suggested or derived from the disclosure of the present invention are to be considered as being within the scope of the present invention.
The method for characterizing the structure and the performance of the polyethenone organic solvent nanofiltration membrane material comprises the following steps:
specific surface area test of Polyetherketone: the adsorption/desorption isotherm of the polyolefin ether ketone to nitrogen was tested and the BET specific surface area and micropore distribution range of the polymer were calculated.
Penetration and selectivity performance test of the polyethenone nanofiltration membrane: cutting a polyethenoxy ether ketone organic solvent nanofiltration membrane, placing the membrane in a cross-flow device with flux and retention rate, wherein the transmembrane pressure is 1MPa, and the flow rate of liquid on the upper surface of the membrane is 0.5L/min. After 24 hours of operation in pure solvent, the flux of the solvent and the retention rate of the organic molecules were tested.
Example 1:
the poly (ether ketone) polymer and PIM-1 are subjected to polycondensation reaction, polymer solutions are prepared according to the following table 1.1, spin coating is performed on a designated ultrafiltration membrane according to the process parameters provided in the table 1.2, and the nanofiltration membrane of an organic solvent is prepared after drying in air at a certain temperature. The solvent flux and molecular cut-off rate of the prepared organic solvent nanofiltration membrane were tested, and the results are shown in table 1.3. The specific surface area and pore size distribution of the present polyolefin ether ketone polymer and the typical self-contained microporous polymer (PIM-1) were tested and the results are shown in Table 1.4.
TABLE 1.1 preparation conditions of Polyetherketone Polymer solutions
TABLE 1.2 preparation conditions of Polyetherketone organic solvent nanofiltration membrane materials
TABLE 1.3 Poly (alkyletherketone) polymer and organic solvent nanofiltration membrane Material Properties
TABLE 1.4 specific surface area and pore size distribution of Polyetherketone and PIM-1
Example 2:
firstly, synthesizing a poly (ether ketone) polymer, preparing a poly (ether ketone) polymer solution according to the process parameters provided in the table 2.1, spin-coating on a designated ultrafiltration membrane according to the process parameters provided in the table 2.2, and drying in air at a certain temperature to obtain the poly (ether ketone) organic solvent nanofiltration membrane. The solvent flux and the molecular rejection rate of the prepared polyethenoxy ether ketone organic solvent nanofiltration membrane are tested, and the results are shown in table 2.3.
TABLE 2.1 preparation conditions of Polyetherketone Polymer solutions
TABLE 2.2 preparation conditions of Polyetherketone organic solvent nanofiltration membrane materials
TABLE 2.3 Polyetherketone Polymer and organic solvent nanofiltration Membrane Material Properties
Example 3:
firstly, synthesizing a poly (ether ketone) polymer, preparing a poly (ether ketone) polymer solution according to the process parameters provided in the table 3.1, spin-coating on a designated ultrafiltration membrane according to the process parameters provided in the table 3.2, and drying in air at a certain temperature to obtain the poly (ether ketone) organic solvent nanofiltration membrane. The solvent flux and the molecular rejection rate of the prepared polyethenoxy ether ketone organic solvent nanofiltration membrane are tested, and the results are shown in table 3.3.
TABLE 3.1 preparation conditions of Polyetherketone Polymer solutions
TABLE 3.2 preparation conditions of Polyetherketone organic solvent nanofiltration membrane materials
TABLE 3.3 Poly (alkyletherketone) polymer and organic solvent nanofiltration membrane Material Properties
Example 4:
firstly, synthesizing a poly (ether ketone) polymer, preparing a poly (ether ketone) polymer solution according to the process parameters provided in the table 4.1, spin-coating on a designated ultrafiltration membrane according to the process parameters provided in the table 4.2, and drying in air at a certain temperature to obtain the poly (ether ketone) organic solvent nanofiltration membrane. The solvent flux and the molecular rejection rate of the prepared polyethenoxy ether ketone organic solvent nanofiltration membrane are tested, and the results are shown in table 4.3.
TABLE 4.1 preparation conditions of Polyetherketone Polymer solutions
TABLE 4.2 preparation conditions of Polyetherketone organic solvent nanofiltration membrane materials
TABLE 4.3 Polyetherketone Polymer and organic solvent nanofiltration Membrane Material Properties
Example 5:
firstly, synthesizing a poly (ether ketone) polymer, preparing a poly (ether ketone) polymer solution according to the process parameters provided in the table 5.1, spin-coating on a designated ultrafiltration membrane according to the process parameters provided in the table 5.2, and drying in air at a certain temperature to obtain the poly (ether ketone) organic solvent nanofiltration membrane. The solvent flux and the molecular rejection rate of the prepared polyethenoxy ether ketone organic solvent nanofiltration membrane are tested, and the results are shown in table 5.3.
TABLE 5.1 preparation conditions of Polyetherketone Polymer solutions
TABLE 5.2 preparation conditions of Polyetherketone organic solvent nanofiltration membrane materials
TABLE 5.3 Polyetherketone Polymer and organic solvent nanofiltration Membrane Material Properties
The technical problems, technical solutions and advantageous effects solved by the present invention have been further described in detail in the above-described embodiments, and it should be understood that the above-described embodiments are only illustrative of the present invention and are not intended to limit the present invention, and any modifications, equivalent substitutions, improvements, etc. within the spirit and principle of the present invention should be included in the scope of protection of the present invention.
Claims (9)
1. A polyethenone organic solvent nanofiltration membrane material and a preparation method thereof are characterized by comprising the following steps,
s1, preparing a polyketone polymer solution, namely completely dissolving the polyketone polymer in an organic solvent, wherein the mass fraction of the polyketone polymer is 0.1-5%, and preparing the polyketone polymer solution;
s2, spin coating is carried out on the surface of the porous support film by using a polyalkene ether ketone polymer solution, wherein the spin coating comprises a first stage and a second stage, the spin coating rotating speed of the first stage is 50-1000 revolutions per minute, the spin coating time is 1-10 seconds, the spin coating rotating speed of the second stage is 500-5000 revolutions per minute, and the spin coating time is 5-60 seconds;
s3, drying the spin-coated porous support membrane, wherein the drying temperature is 15-100 ℃, the drying time is 1-60 minutes, and the polyolefin ether ketone organic solvent nanofiltration membrane material is prepared after the drying is completed;
the structural formula of the poly (ether ketone) polymer is as follows:
in the structural formula of the polyethenoxy ketone polymer, the structural formula of R1 and R2 is as follows:
and R1 is selected from any one of (1) to (3), and R2 is selected from any one of (4) to (6), wherein the positions of the acyl alkynyl and the hydroxyl functional groups are shown.
2. The nano-filtration membrane material of the organic solvent of the poly (ether ketone) and the preparation method thereof according to claim 1, wherein the organic solvent in S1 is one or more of tetrahydrofuran, dichloromethane, chloroform, N-dimethylformamide and N, N-dimethylacetamide.
3. The nano-filtration membrane material of the organic solvent of the poly (ether ketone) and the preparation method thereof according to claim 2, wherein the mass fraction of the poly (ether ketone) polymer in S1 is 0.5-2%.
4. The nano-filtration membrane material of the organic solvent of the poly (ether ketone) and the preparation method thereof according to claim 3, wherein the mass fraction of the poly (ether ketone) polymer in S1 is 1%.
5. The polyethenone organic solvent nanofiltration membrane material and the preparation method thereof according to claim 1, wherein the porous support membrane in the S2 is any one of polyimide, polyacrylonitrile and polyether-ether-ketone polymer ultrafiltration membrane or alumina, silicon carbide and zirconia inorganic ceramic ultrafiltration membrane.
6. The polyethenone organic solvent nanofiltration membrane material and the preparation method thereof according to claim 1, wherein the spin-coating rotation speed in the first stage in S2 is 200-600 rpm, and the spin-coating time is 2-5 seconds; the spin coating rotating speed of the second stage in the S2 is 1000-3000 rpm, and the spin coating time is 20-50 seconds.
7. The polyethenone organic solvent nanofiltration membrane material and the preparation method thereof according to claim 6, wherein the spin-coating rotation speed in the first stage in S2 is 500 rpm, and the spin-coating time is 3 seconds; the spin-coating speed in the second stage in S2 was 2000 rpm and the spin-coating time was 40 seconds.
8. The nanofiltration membrane material of the organic solvent of the poly (ether ketone) and the preparation method thereof according to claim 1, wherein the drying temperature in S3 is 20-60 ℃ and the drying time is 2-30 minutes.
9. The nano-filtration membrane material of the organic solvent of the poly (ether ketone) and the preparation method thereof according to claim 8, wherein the drying temperature in S3 is 30 ℃ and the drying time is 5 minutes.
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