CN115253728A - Preparation method of polyimide fiber solvent-resistant nanofiltration membrane - Google Patents

Preparation method of polyimide fiber solvent-resistant nanofiltration membrane Download PDF

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CN115253728A
CN115253728A CN202211026244.8A CN202211026244A CN115253728A CN 115253728 A CN115253728 A CN 115253728A CN 202211026244 A CN202211026244 A CN 202211026244A CN 115253728 A CN115253728 A CN 115253728A
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solvent
nanofiltration membrane
membrane
polyimide fiber
resistant nanofiltration
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李纯
赵勇
翟哲
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Shandong Nafeibo Technology Development Co ltd
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    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D71/00Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
    • B01D71/06Organic material
    • B01D71/58Other polymers having nitrogen in the main chain, with or without oxygen or carbon only
    • B01D71/62Polycondensates having nitrogen-containing heterocyclic rings in the main chain
    • B01D71/64Polyimides; Polyamide-imides; Polyester-imides; Polyamide acids or similar polyimide precursors
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D61/00Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
    • B01D61/02Reverse osmosis; Hyperfiltration ; Nanofiltration
    • B01D61/027Nanofiltration
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D67/00Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
    • B01D67/0002Organic membrane manufacture
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D67/00Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
    • B01D67/0002Organic membrane manufacture
    • B01D67/0006Organic membrane manufacture by chemical reactions
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D69/00Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
    • B01D69/02Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor characterised by their properties
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D2323/00Details relating to membrane preparation
    • B01D2323/39Electrospinning

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  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Nanotechnology (AREA)
  • Water Supply & Treatment (AREA)
  • Artificial Filaments (AREA)
  • Separation Using Semi-Permeable Membranes (AREA)

Abstract

The invention discloses a preparation method of a polyimide fiber solvent-resistant nanofiltration membrane, which comprises the following steps: (1) obtaining a polyamic acid solution; (2) Mixing the polyamic acid solution with the polymer aqueous solution, and performing electrostatic spinning to obtain a fiber membrane; the polymer is polyvinyl alcohol and/or polyethylene glycol; (3) Carrying out heat treatment on the fiber membrane obtained in the step (2) for primary imidization; (4) Immersing the membrane obtained in the step (3) into a mixed solution of pyridine and acetic anhydride for secondary imidization; (5) And (4) immersing the membrane obtained in the step (3) into an amine solution for a crosslinking reaction to obtain the polyimide fiber solvent-resistant nanofiltration membrane. The invention adopts the electrostatic spinning method to prepare the polyimide fiber solvent-resistant nanofiltration membrane, and has the advantages of large solvent permeation flux, good chemical stability and long-term service performance.

Description

Preparation method of polyimide fiber solvent-resistant nanofiltration membrane
Technical Field
The invention belongs to the field of membrane materials and separation application thereof, and particularly relates to a preparation method of a polyimide fiber solvent-resistant nanofiltration membrane.
Background
A large amount of organic solvents are needed in the fields of chemical industry, food, medicine and the like, and efficient separation of substances in the organic solvents and treatment of waste solvents are important problems in practical production. Compared with the traditional separation modes such as distillation, extraction, crystallization and the like, the membrane technology has the advantages of low energy consumption, low cost, easy industrial amplification and the like. The solvent-resistant nanofiltration membrane belongs to a special nanofiltration membrane, has the aperture of about 1nm, and can separate molecules with the molecular weight of 200-1000g/mol from an organic solvent. At present, the solvent-resistant nanofiltration membrane mainly has two structural forms, namely an asymmetric membrane and a composite membrane, and compared with the asymmetric membrane, the asymmetric membrane has excellent chemical stability, and the commercial solvent-resistant nanofiltration membrane mainly takes the asymmetric membrane as a main component. Polyimide is widely used for preparing asymmetric solvent-resistant nanofiltration membranes as a polymer with excellent performance, but the permeation flux is low (Journal of Membrane Science,2002,205 (1-2): 191-202.). Although the permeation flux of the polyimide solvent-resistant nanofiltration membrane can be improved by adding nanomaterials such as graphene oxide (Chemical Engineering Research and Design,2019,146, 182-189.), carbon nanotubes (Chemical Engineering Journal,2018,345, 174-185) and MOF (Environmental Research,2020, 183.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a preparation method of a polyimide fiber solvent-resistant nanofiltration membrane.
The specific technical scheme is as follows:
a preparation method of a polyimide fiber solvent-resistant nanofiltration membrane comprises the following steps:
(1) Obtaining polyamic acid, specifically a polyamic acid solution with a certain solid content;
(2) Mixing the polyamic acid solution with the polymer aqueous solution, and performing electrostatic spinning to obtain a fiber membrane; the polymer is polyvinyl alcohol and/or polyethylene glycol;
(3) Carrying out heat treatment on the fiber membrane obtained in the step (2) for primary imidization;
(4) Immersing the membrane obtained in the step (3) into a mixed solution of pyridine and acetic anhydride for secondary imidization;
(5) And (5) immersing the membrane obtained in the step (4) into an amine solution for cross-linking reaction to obtain the polyimide fiber solvent-resistant nanofiltration membrane.
Further, in the step (1): the polyamic acid solution is prepared by synthesizing 3,3', 4' -biphenyl tetracarboxylic dianhydride and m-phenylenediamine with the molar ratio of (0.8-1.2) to 1. The molar ratio of 3,3',4,4' -biphenyltetracarboxylic dianhydride to m-phenylenediamine is preferably 1.2.
Further, in the step (1): the solid content of the polyamic acid solution is 20-40%.
Further, in the step (1): the solvent for the reaction is N, N-dimethylacetamide.
Further, in the step (1): reaction in N 2 Under the protection of the catalyst.
Further, in the step (1): the reaction temperature is preferably 15 to 50 ℃.
Further, in the step (1): the reaction time is preferably 0.5 to 2 hours.
Further, in the step (2): the concentration of the polymer aqueous solution is 5-35 wt%.
Further, in the step (2): the mass ratio of the polyamic acid solution to the polymer aqueous solution is (0.1-10): 1.
Further, in the step (2): the electrostatic spinning takes non-woven fabrics as a substrate.
Further, in the step (2): the conditions for electrospinning are preferably: the voltage is 10-25 kV, and the spinning speed is 0.5-5 mL/h.
Further, in the step (3): the heat treatment temperature is 50-200 ℃, and the heat treatment time is 5-20 hours. The heat treatment is preferably carried out in an oven.
Further, in the step (4): in the mixed solution of pyridine and acetic anhydride, the molar ratio of pyridine to acetic anhydride is (0.5-3): 1.
Further, in the step (4): the soaking time is 2-30 hours.
Further, in the step (5): the amine is one or a mixture of more than two of ethylenediamine, polyethyleneimine, piperazine, m-phenylenediamine and hexamethylenediamine.
Further, in the step (5): the amine solution is an aqueous solution of amine, and the concentration of the amine solution is 0.2 to 10 weight percent.
Further, in the step (5): the crosslinking time is 1 to 30 hours.
The invention has the following beneficial effects:
the invention adopts the electrostatic spinning method to prepare the polyimide fiber solvent-resistant nanofiltration membrane, and has the advantages of large solvent permeation flux, good chemical stability and long-term service performance.
Drawings
FIG. 1 shows the separation performance of the polyimide fiber solvent-resistant nanofiltration membrane in example 1 of the present invention on three solvent systems;
FIG. 2 is a graph showing the long-term service performance change of the polyimide fiber solvent-resistant nanofiltration membrane in the ethanol-rose bengal system in example 1 of the present invention.
Detailed Description
The principles and features of this invention are described below in conjunction with examples, which are included to illustrate the invention and not to limit the scope of the invention.
Example 1
The preparation method of the polyimide fiber solvent-resistant nanofiltration membrane comprises the following steps:
(1) At N 2 Under protection, 3', 4' -biphenyl tetracarboxylic dianhydride and m-phenylenediamine in a molar ratio of 1.2 are put into reaction, N-dimethylacetamide is used as a solvent, and the reaction is carried out for 2 hours at 15 ℃ to synthesize a polyamic acid solution with 20% of solid content;
(2) Mixing the polyamic acid solution obtained in the step (1) with a 5wt% polyvinyl alcohol aqueous solution according to a mass ratio of 0.1; electrostatic spinning conditions: the voltage is 25kV, and the spinning speed is 5mL/h;
(3) Placing the fiber membrane obtained in the step (2) in an oven at 50 ℃ for 20 hours, and carrying out primary imidization;
(4) Immersing the membrane obtained in the step (3) into a mixed solution of pyridine and acetic anhydride at the normal temperature, wherein the molar ratio of the pyridine to the acetic anhydride is 1.6;
(5) And (3) immersing the membrane obtained in the step (4) into a 0.2wt% ethylenediamine aqueous solution for crosslinking reaction for 30 hours at normal temperature to obtain the polyimide fiber solvent-resistant nanofiltration membrane.
The polyimide fiber solvent-resistant nanofiltration membrane obtained by the method is subjected to separation performance test, and the test method comprises the following steps: the test is carried out under the condition of cross flow, the test pressure is 0.5MPa, the feed liquid is 0.5g/L rose bengal ethanol solution, 0.5g/L rose bengal methanol solution and 0.5g/L rose bengal isopropanol solution, and the temperature of the feed liquid is 25 ℃.
The separation performance of the polyimide fiber solvent-resistant nanofiltration membrane on an ethanol-rose bengal system is measured as follows: the ethanol permeation flux is 12.1 L.m -2 ·h -1 ·bar -1 The retention of rose bengal is 96.9%.
The separation performance of the polyimide fiber solvent-resistant nanofiltration membrane on different solvent systems is shown in fig. 1, and the obtained polyimide fiber solvent-resistant nanofiltration membrane has high interception capability in methanol, ethanol and isopropanol, which indicates that the polyimide fiber solvent-resistant nanofiltration membrane has good chemical stability.
The measured change of the long-term service performance of the polyimide fiber solvent-resistant nanofiltration membrane on an ethanol-rose bengal system is shown in fig. 2, and the obtained polyimide fiber solvent-resistant nanofiltration membrane has good long-term stability.
Example 2
The preparation method of the polyimide fiber solvent-resistant nanofiltration membrane comprises the following steps:
(1) At N 2 Under protection, 3', 4' -biphenyl tetracarboxylic dianhydride and m-phenylenediamine in a molar ratio of 1.2 are put into reaction, N-dimethylacetamide is used as a solvent, and the reaction is carried out for 0.5 hour at 50 ℃ to synthesize a polyamic acid solution with the solid content of 40%;
(2) Mixing the polyamic acid solution obtained in the step (1) with a polyvinyl alcohol aqueous solution with the mass ratio of 10; electrostatic spinning conditions: the voltage is 10kV, and the spinning speed is 0.5mL/h;
(3) Placing the fiber membrane obtained in the step (2) in an oven at 200 ℃ for 5 hours for primary imidization;
(4) Immersing the membrane obtained in the step (3) into a mixed solution of pyridine and acetic anhydride at the normal temperature, wherein the molar ratio of the pyridine to the acetic anhydride is 2.5;
(5) And (5) immersing the membrane obtained in the step (4) into a 10wt% m-phenylenediamine aqueous solution at normal temperature for crosslinking reaction for 30 hours to obtain the polyimide fiber solvent-resistant nanofiltration membrane.
The polyimide fiber obtained above was subjected to a separation performance test using a solvent-resistant nanofiltration membrane, according to the test method described in example 1. The separation performance of the polyimide fiber solvent-resistant nanofiltration membrane is measured as follows: the ethanol permeation flux is 10.6 L.m -2 ·h -1 ·bar -1 The retention of rose bengal is 98.4%.
Example 3
The preparation method of the polyimide fiber solvent-resistant nanofiltration membrane comprises the following steps:
(1) In N 2 Under protection, 3', 4' -biphenyl tetracarboxylic dianhydride and m-phenylenediamine in a molar ratio of 1.2 are put into reaction, N-dimethylacetamide is used as a solvent, and the reaction is carried out for 1 hour at 25 ℃ to synthesize a polyamic acid solution with 20% of solid content;
(2) Mixing the polyamic acid solution obtained in the step (1) with a 20wt% polyethylene glycol aqueous solution according to a mass ratio of 5; electrostatic spinning conditions: the voltage is 20kV, and the spinning speed is 3mL/h;
(3) Placing the fiber membrane obtained in the step (2) in a drying oven at 100 ℃ for 10 hours for primary imidization;
(4) Immersing the membrane obtained in the step (3) into a mixed solution of pyridine and acetic anhydride at the normal temperature, wherein the molar ratio of the pyridine to the acetic anhydride is 0.5;
(5) And (3) immersing the membrane obtained in the step (4) into a 6wt% polyethylene imine water solution for crosslinking reaction for 15 hours at normal temperature to obtain the polyimide fiber solvent-resistant nanofiltration membrane.
The polyimide fiber solvent-resistant nanofiltration membrane obtained above was subjected to a separation performance test, the test method referring to example 1. The separation performance of the polyimide fiber solvent-resistant nanofiltration membrane is measured as follows: ethanol infiltrationThe flux was 9.6 L.m -2 ·h -1 ·bar -1 The retention of rose bengal is 98.8%.
Example 4
The preparation method of the polyimide fiber solvent-resistant nanofiltration membrane comprises the following steps:
(1) In N 2 Under protection, 3', 4' -biphenyl tetracarboxylic dianhydride and m-phenylenediamine in a molar ratio of 1.2 are put into reaction, N-dimethylacetamide is used as a solvent, and the reaction is carried out for 1 hour at 25 ℃ to synthesize a polyamic acid solution with a solid content of 30%;
(2) Mixing the polyamic acid solution obtained in the step (1) with a 20wt% polyethylene glycol aqueous solution according to a mass ratio of 6; electrostatic spinning conditions: the voltage is 25kV, and the spinning speed is 5mL/h;
(3) Placing the fiber membrane obtained in the step (2) in an oven at 100 ℃ for 5 hours for primary imidization;
(4) Immersing the membrane obtained in the step (3) into a mixed solution of pyridine and acetic anhydride at the normal temperature, wherein the molar ratio of the pyridine to the acetic anhydride is 3;
(5) And (3) immersing the membrane obtained in the step (4) into a mixed aqueous solution of 5wt% of polyethyleneimine and piperazine for crosslinking reaction at normal temperature, wherein the mass ratio of the polyethyleneimine to the piperazine is 2.
The polyimide fiber solvent-resistant nanofiltration membrane obtained above was subjected to a separation performance test, the test method referring to example 1. The separation performance of the polyimide fiber solvent-resistant nanofiltration membrane is measured as follows: the ethanol permeation flux is 12.3 L.m -2 ·h -1 ·bar -1 The retention of rose bengal is 98.0%.
Example 5
The preparation method of the polyimide fiber solvent-resistant nanofiltration membrane comprises the following steps:
(1) In N 2 Under protection, 3', 4' -biphenyl tetracarboxylic dianhydride and m-phenylenediamine in a molar ratio of 1.2 are put into reaction, N-dimethylacetamide is used as a solvent, and the reaction is carried out at 30 ℃ for 1Synthesizing a polyamic acid solution with the solid content of 40 percent in hours;
(2) Mixing the polyamic acid solution obtained in the step (1) with 20wt% of mixed aqueous solution of polyethylene glycol and polyvinyl alcohol according to the mass ratio of 1; electrostatic spinning conditions are as follows: the voltage is 10kV, and the spinning speed is 1mL/h;
(3) Placing the fiber membrane obtained in the step (2) in an oven at 150 ℃ for 8 hours for primary imidization;
(4) Immersing the membrane obtained in the step (3) into a mixed solution of pyridine and acetic anhydride at the normal temperature, wherein the molar ratio of the pyridine to the acetic anhydride is 1;
(5) And (3) immersing the membrane obtained in the step (4) into a 1wt% hexamethylene diamine aqueous solution for crosslinking reaction for 10 hours at normal temperature to obtain the polyimide fiber solvent-resistant nanofiltration membrane.
The polyimide fiber solvent-resistant nanofiltration membrane obtained above was subjected to a separation performance test, the test method referring to example 1. The separation performance of the polyimide fiber solvent-resistant nanofiltration membrane is measured as follows: the ethanol permeation flux is 10.7 L.m -2 ·h -1 ·bar -1 The retention of rose bengal is 99.1%.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.

Claims (9)

1. A preparation method of a polyimide fiber solvent-resistant nanofiltration membrane is characterized by comprising the following steps:
(1) Obtaining a polyamic acid solution;
(2) Mixing the polyamic acid solution with the polymer aqueous solution, and performing electrostatic spinning to obtain a fiber membrane; the polymer is polyvinyl alcohol and/or polyethylene glycol;
(3) Carrying out heat treatment on the fiber membrane obtained in the step (2) to carry out primary imidization;
(4) Immersing the membrane obtained in the step (3) into a mixed solution of pyridine and acetic anhydride for secondary imidization;
(5) And (5) immersing the membrane obtained in the step (4) into an amine solution for cross-linking reaction to obtain the polyimide fiber solvent-resistant nanofiltration membrane.
2. The method according to claim 1, wherein in the step (1): the polyamic acid solution is prepared by synthesizing 3,3', 4' -biphenyl tetracarboxylic dianhydride and m-phenylenediamine in a molar ratio of (0.8-1.2): 1.
3. The production method according to claim 1 or 2, characterized in that, in step (1): the solid content of the polyamic acid solution is 20-40%.
4. The production method according to claim 1 or 2, characterized in that in step (2):
the concentration of the polymer aqueous solution is 5-35 wt%;
the mass ratio of the polyamic acid solution to the polymer aqueous solution is (0.1-10): 1.
5. The production method according to claim 1 or 2, characterized in that in step (2): the electrostatic spinning takes non-woven fabrics as a substrate.
6. The production method according to claim 1 or 2, characterized in that, in step (3): the heat treatment temperature is 50-200 ℃, and the heat treatment time is 5-20 hours.
7. The production method according to claim 1 or 2, characterized in that, in step (4):
in the mixed solution of pyridine and acetic anhydride, the molar ratio of pyridine to acetic anhydride is (0.5-3) to 1;
the soaking time is 2-30 hours.
8. The production method according to claim 1 or 2, characterized in that, in step (5):
the amine is one or a mixture of more than two of ethylenediamine, polyethyleneimine, piperazine, m-phenylenediamine and hexamethylenediamine;
the concentration of the amine solution is 0.2-10 wt%;
the crosslinking time is 1 to 30 hours.
9. A polyimide fiber solvent-resistant nanofiltration membrane obtained by applying the preparation method of any one of claims 1 to 8.
CN202211026244.8A 2022-08-25 2022-08-25 Preparation method of polyimide fiber solvent-resistant nanofiltration membrane Pending CN115253728A (en)

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Citations (8)

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Publication number Priority date Publication date Assignee Title
EP0753336A2 (en) * 1995-07-12 1997-01-15 Bend Research, Inc. Solvent resistant microporous polyimide membranes
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US20130112619A1 (en) * 2010-07-19 2013-05-09 Imperial Innovations Limited Solvent resistant polyamide nanofiltration membranes
CN104630990A (en) * 2015-02-10 2015-05-20 北京化工大学常州先进材料研究院 Polyimide fiber membrane with cross-linking morphology and preparation method of polyimide fiber membrane
KR20160052870A (en) * 2014-10-29 2016-05-13 연세대학교 산학협력단 Manufacturing Method of Polyimide-Based Composite Membrane
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Publication number Priority date Publication date Assignee Title
EP0753336A2 (en) * 1995-07-12 1997-01-15 Bend Research, Inc. Solvent resistant microporous polyimide membranes
US6113794A (en) * 1999-01-25 2000-09-05 Kumar; Ashwani Composite solvent resistant nanofiltration membranes
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