CN113529205A - Super-crosslinked porous polymer fiber and preparation method thereof - Google Patents
Super-crosslinked porous polymer fiber and preparation method thereof Download PDFInfo
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- CN113529205A CN113529205A CN202110886513.7A CN202110886513A CN113529205A CN 113529205 A CN113529205 A CN 113529205A CN 202110886513 A CN202110886513 A CN 202110886513A CN 113529205 A CN113529205 A CN 113529205A
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- D01F6/88—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds
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- D01F11/00—Chemical after-treatment of artificial filaments or the like during manufacture
- D01F11/04—Chemical after-treatment of artificial filaments or the like during manufacture of synthetic polymers
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Abstract
The invention relates to a super-crosslinked porous polymer fiber and a preparation method thereof, wherein a macromonomer and a catalyst are dissolved in a good solvent 1, 2-dichloroethane, and then added into a poor solvent simethicone, under the influence of solubility difference, the macromonomer is separated out and forms filaments under the action of orientation and stretching by mechanical stirring, the simethicone can separate the stretched filaments, the liquid filaments can stably exist in a reaction system, and finally, the super-crosslinked porous polymer fiber is formed by carrying out super-crosslinking reaction under the action of the catalyst and curing. The method can realize the rapid synthesis of the super-crosslinked polymer fiber with larger size (millimeter-scale length and micron-scale diameter), large length-diameter ratio and high specific surface area, and the obtained material can be widely applied in the fields of water pollutant removal, gas adsorption separation, protein imprinting carriers and the like, and can be converted into porous carbon fiber for use after carbonization.
Description
Technical Field
The invention belongs to the field of porous polymer materials, and relates to a super-crosslinked porous polymer fiber and a preparation method thereof.
Background
The hypercrosslinked polymer is a porous polymer material with a bridging network structure formed by rigid aromatic monomers through a friedel-crafts alkylation reaction, has the advantages of light weight, controllable pore structure, large specific surface area, good thermal stability, chemical stability and the like, and is widely applied to the fields of water treatment, heterogeneous catalysis, gas adsorption and separation and the like. The super-crosslinked polymer fiber has a one-dimensional structure different from that of a granular material, is easy to assemble into a three-dimensional network by overlapping and winding, has remarkably enhanced mechanical properties, and has more obvious advantages in the application process. Therefore, the development of a synthetic method of the super-crosslinked polymer fiber has important significance for preparing a high-performance porous polymer material.
The synthesis strategy of the super-crosslinked polymer fiber is mainly a template method, and usually comprises the steps of adding a template agent into a reaction system, and polymerizing an aromatic small-molecular monomer on the surface of the template agent to form a fiber structure (Polym. chem.2019,10,4239; ACS appl. Mater. interfaces 2017,9, 20779). Or a bottle brush-shaped copolymer precursor is prepared by an organic synthesis means, a main chain of the precursor is used as a template, and a large number of aromatic rings of a side chain of the precursor are woven under the action of an external cross-linking agent to form a hypercrosslinked structure, so that hypercrosslinked polymer fibers are obtained. At present, reports of synthesizing the super-crosslinked polymer fiber by a simple one-step method by using aromatic macromolecules as monomers are not found, and the invention is expected to further enrich the synthetic method of the super-crosslinked polymer fiber.
Disclosure of Invention
Technical problem to be solved
In order to avoid the defects of the prior art, the invention provides a hypercrosslinked porous polymer fiber and a preparation method thereof, and provides a new strategy for preparing the hypercrosslinked porous polymer fiber by using aromatic macromolecules containing chlorobenzyl or bromobenzyl as monomers. The method comprises the steps of dissolving a macromonomer and a catalyst in a good solvent 1, 2-dichloroethane, adding the mixture into poor solvent dimethyl silicone oil, separating out the macromonomer under the influence of solubility difference, forming filaments under the action of orientation drawing by mechanical stirring, separating the drawn filaments by the dimethyl silicone oil, enabling the liquid filaments to stably exist in a reaction system without coalescence, finally carrying out a hyper-crosslinking reaction under the action of the catalyst, and curing to form the hyper-crosslinked porous polymer fiber. The method can realize the rapid synthesis of the super-crosslinked polymer fiber with larger size (millimeter-scale length and micron-scale diameter), large length-diameter ratio and high specific surface area.
Technical scheme
A super-crosslinked porous polymer fiber is characterized in that a macromolecular monomer is subjected to super-crosslinking reaction under the action of a catalyst, and polymerized to form the super-crosslinked porous polymer fiber; microscopic molecular structure: linear polymer molecular chains with polystyrene structures with different polymerization degrees are subjected to methylene phase crosslinking through random occurrence of friedel-crafts alkylation reaction among chains; forming the super-crosslinked polymer fiber with large length-diameter ratio and high specific surface area with millimeter-scale length and micron-scale diameter.
The macromers include:
the catalyst is anhydrous ferric trichloride or anhydrous aluminum trichloride.
A method for preparing said hypercrosslinked porous polymer fiber characterized by the steps of:
step 1: under the assistance of ultrasound, dissolving a macromonomer in 1, 2-dichloroethane to obtain a solution I; the concentration of the macromonomer in the solution I is 0.02-0.07 g/mL;
step 2: under the assistance of ultrasound, dissolving a catalyst in 1, 2-dichloroethane to obtain a solution II; the concentration of the catalyst in the solution II is 0.01-0.05 g/mL;
and step 3: adding dimethyl silicone oil into the container, placing the container in an oil bath pot, and heating to 42-52 ℃;
and 4, step 4: under the mechanical stirring, sequentially adding the solution I and the solution II into a three-necked bottle, and stirring for 4-8h at the rotating speed of 300-400 r/min;
the volume ratio of the simethicone to the solution I to the solution II is 10: 0.5-1.5: 0.4-1.2;
and 5: raising the temperature of the system to 78-85 ℃, and continuing to react for 6-12 h;
step 6: and cooling to room temperature after the reaction is finished, performing product separation by suction filtration, washing for multiple times by using 1, 2-dichloroethane, performing soxhlet extraction for more than 18 hours by using ethanol, and drying to obtain the super-crosslinked porous polymer fiber.
The viscosity of the dimethyl silicone oil is 25-150 cs.
The washing with 1, 2-dichloroethane in the step 6 is carried out for 2 times.
Advantageous effects
The invention provides a super-crosslinked porous polymer fiber and a preparation method thereof, which are characterized in that a macromonomer and a catalyst are dissolved in a good solvent 1, 2-dichloroethane, and then added into a poor solvent simethicone, under the influence of solubility difference, the macromonomer is separated out, filaments are formed under the action of orientation drawing by mechanical stirring, the simethicone can separate the drawn filaments, the liquid filaments can stably exist in a reaction system, and finally, the super-crosslinked porous polymer fiber is formed by carrying out super-crosslinking reaction under the action of the catalyst and curing. The method can realize the rapid synthesis of the super-crosslinked polymer fiber with larger size (millimeter-scale length and micron-scale diameter), large length-diameter ratio and high specific surface area, and the obtained material can be widely applied in the fields of water pollutant removal, gas adsorption separation, protein imprinting carriers and the like, and can be converted into porous carbon fiber for use after carbonization.
Drawings
FIG. 1 is SEM (A) and TEM (B) photographs of a hypercrosslinked porous polymer fiber
FIG. 2 is N of a hypercrosslinked porous polymer fiber2An adsorption-desorption isotherm (A) and a pore size distribution curve (B); the specific surface area is 501.1m2In terms of/g, the mean pore diameter was 6.42 nm.
Detailed Description
The invention will now be further described with reference to the following examples and drawings:
example 1: preparation of hypercrosslinked porous polymer fibers
Under the assistance of ultrasound, 0.8g of monomer 1 is dissolved in 18mL of 1, 2-dichloroethane to obtain a solution I, and 0.4g of anhydrous ferric trichloride is dissolved in 8mL of 1, 2-dichloroethane to obtain a solution II; adding 150mL of dimethyl silicone oil with the viscosity of 100cs into a 250mL three-neck flask, placing the mixture into an oil bath pot, heating the mixture to 42 ℃, sequentially adding the solution I and the solution II into the three-neck flask under mechanical stirring at 350r/min, and stirring for 5 hours; and raising the temperature of the system to 82 ℃, continuously reacting for 8 hours, cooling to room temperature after the reaction is finished, performing product separation by suction filtration, washing for 2 times by using 1, 2-dichloroethane, performing Soxhlet extraction for 24 hours by using ethanol, and drying to obtain the super-crosslinked porous polymer fiber.
Example 2: preparation of hypercrosslinked porous polymer fibers
Under the assistance of ultrasound, 1.5g of monomer 2 is dissolved in 30mL of 1, 2-dichloroethane to obtain a solution I, and 0.5g of anhydrous aluminum trichloride is dissolved in 20mL of 1, 2-dichloroethane to obtain a solution II; adding 300mL of dimethyl silicone oil with the viscosity of 50cs into a 500mL three-neck flask, placing the mixture into an oil bath pot, heating the mixture to 42 ℃, sequentially adding the solution I and the solution II into the three-neck flask under mechanical stirring at 300r/min, and stirring for 4 hours; and raising the temperature of the system to 82 ℃, continuing to react for 10 hours, cooling to room temperature after the reaction is finished, performing product separation by suction filtration, washing for 2 times by using 1, 2-dichloroethane, performing Soxhlet extraction for 24 hours by using ethanol, and drying to obtain the super-crosslinked porous polymer fiber.
Example 3: preparation of hypercrosslinked porous polymer fibers
Under the assistance of ultrasound, 0.25g of monomer 5 is dissolved in 6mL of 1, 2-dichloroethane to obtain a solution I, and 0.2g of anhydrous ferric trichloride is dissolved in 4mL of 1, 2-dichloroethane to obtain a solution II; adding 60mL of dimethyl silicone oil with the viscosity of 150cs into a 100mL three-neck flask, placing the mixture into an oil bath pot, heating the mixture to 42 ℃, sequentially adding the solution I and the solution II into the three-neck flask under mechanical stirring at 350r/min, and stirring for 5 hours; and raising the temperature of the system to 82 ℃, continuously reacting for 6 hours, cooling to room temperature after the reaction is finished, performing product separation by suction filtration, washing for 2 times by using 1, 2-dichloroethane, performing Soxhlet extraction for 24 hours by using ethanol, and drying to obtain the super-crosslinked porous polymer fiber.
Example 4: preparation of hypercrosslinked porous polymer fibers
Under the assistance of ultrasound, 3.5g of monomer 6 is dissolved in 50mL of 1, 2-dichloroethane to obtain a solution I, and 1.5g of anhydrous ferric trichloride is dissolved in 40mL of 1, 2-dichloroethane to obtain a solution II; adding 600mL of dimethyl silicone oil with the viscosity of 100cs into a 1L three-neck flask, placing the mixture into an oil bath pot, heating the mixture to 42 ℃, sequentially adding the solution I and the solution II into the three-neck flask under mechanical stirring at 400r/min, and stirring for 6 hours; and raising the temperature of the system to 82 ℃, continuing to react for 10 hours, cooling to room temperature after the reaction is finished, performing product separation by suction filtration, washing for 2 times by using 1, 2-dichloroethane, performing Soxhlet extraction for 24 hours by using ethanol, and drying to obtain the super-crosslinked porous polymer fiber.
Example 5: preparation of hypercrosslinked porous polymer fibers
Under the assistance of ultrasound, 0.7g of monomer 7 is dissolved in 10mL of 1, 2-dichloroethane to obtain a solution I, and 0.1g of anhydrous aluminum trichloride is dissolved in 8mL of 1, 2-dichloroethane to obtain a solution II; adding 150mL of dimethyl silicone oil with the viscosity of 150cs into a 250mL three-neck flask, placing the mixture into an oil bath pot, heating the mixture to 42 ℃, sequentially adding the solution I and the solution II into the three-neck flask under mechanical stirring at 400r/min, and stirring for 4 hours; and raising the temperature of the system to 82 ℃, continuously reacting for 8 hours, cooling to room temperature after the reaction is finished, performing product separation by suction filtration, washing for 2 times by using 1, 2-dichloroethane, performing Soxhlet extraction for 24 hours by using ethanol, and drying to obtain the super-crosslinked porous polymer fiber.
Example 6: preparation of hypercrosslinked porous polymer fibers
Under the assistance of ultrasound, 1.8g of monomer 8 is dissolved in 40mL of 1, 2-dichloroethane to obtain a solution I, and 0.75g of anhydrous ferric trichloride is dissolved in 15mL of 1, 2-dichloroethane to obtain a solution II; adding 300mL of dimethyl silicone oil with the viscosity of 50cs into a 500mL three-neck flask, placing the mixture into an oil bath pot, heating the mixture to 42 ℃, sequentially adding the solution I and the solution II into the three-neck flask under mechanical stirring at 300r/min, and stirring for 4 hours; and raising the temperature of the system to 82 ℃, continuously reacting for 8 hours, cooling to room temperature after the reaction is finished, performing product separation by suction filtration, washing for 2 times by using 1, 2-dichloroethane, performing Soxhlet extraction for 24 hours by using ethanol, and drying to obtain the super-crosslinked porous polymer fiber.
Claims (6)
1. A super-crosslinked porous polymer fiber is characterized in that a macromolecular monomer is subjected to super-crosslinking reaction under the action of a catalyst, and polymerized to form the super-crosslinked porous polymer fiber; microscopic molecular structure: linear polymer molecular chains with polystyrene structures with different polymerization degrees are subjected to methylene phase crosslinking through random occurrence of friedel-crafts alkylation reaction among chains; forming the super-crosslinked polymer fiber with large length-diameter ratio and high specific surface area with millimeter-scale length and micron-scale diameter.
3. the hypercrosslinked porous polymeric fiber of claim 1, wherein: the catalyst is anhydrous ferric trichloride or anhydrous aluminum trichloride.
4. A method of preparing a hypercrosslinked porous polymer fiber according to claim 1 or 2 or 3, characterized by the steps of:
step 1: under the assistance of ultrasound, dissolving a macromonomer in 1, 2-dichloroethane to obtain a solution I; the concentration of the macromonomer in the solution I is 0.02-0.07 g/mL;
step 2: under the assistance of ultrasound, dissolving a catalyst in 1, 2-dichloroethane to obtain a solution II; the concentration of the catalyst in the solution II is 0.01-0.05 g/mL;
and step 3: adding dimethyl silicone oil into the container, placing the container in an oil bath pot, and heating to 42-52 ℃;
and 4, step 4: under the mechanical stirring, sequentially adding the solution I and the solution II into a three-necked bottle, and stirring for 4-8h at the rotating speed of 300-400 r/min;
the volume ratio of the simethicone to the solution I to the solution II is 10: 0.5-1.5: 0.4-1.2;
and 5: raising the temperature of the system to 78-85 ℃, and continuing to react for 6-12 h;
step 6: and cooling to room temperature after the reaction is finished, performing product separation by suction filtration, washing for multiple times by using 1, 2-dichloroethane, performing soxhlet extraction for more than 18 hours by using ethanol, and drying to obtain the super-crosslinked porous polymer fiber.
5. The method of claim 4, wherein: the viscosity of the dimethyl silicone oil is 25-150 cs.
6. The method of claim 4, wherein: the washing with 1, 2-dichloroethane in the step 6 is carried out for 2 times.
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CN114471487A (en) * | 2022-01-28 | 2022-05-13 | 河北工业大学 | Soluble processed super-crosslinked porous polymer material and preparation method thereof |
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CN114471487A (en) * | 2022-01-28 | 2022-05-13 | 河北工业大学 | Soluble processed super-crosslinked porous polymer material and preparation method thereof |
CN114471487B (en) * | 2022-01-28 | 2023-09-08 | 河北工业大学 | Super-crosslinked porous polymer material capable of being dissolved and processed and preparation method thereof |
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