CN110773241A - Preparation method of organic solvent-resistant cation exchange membrane - Google Patents
Preparation method of organic solvent-resistant cation exchange membrane Download PDFInfo
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
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- B01J39/18—Macromolecular compounds
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- C08J5/20—Manufacture of shaped structures of ion-exchange resins
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- C08J5/2218—Synthetic macromolecular compounds
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- C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
- C08J2377/10—Polyamides derived from aromatically bound amino and carboxyl groups of amino carboxylic acids or of polyamines and polycarboxylic acids
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Abstract
The invention discloses a preparation method of a cation exchange membrane, which comprises the following steps: (1) mixing Kevlar aramid fiber material, potassium hydroxide and dimethyl sulfoxide solvent in proportion, sealing and stirring to perform amide partial hydrolysis reaction, dissolving the Kevlar aramid fiber material into nano-fiber casting solution with amino, and scraping the nano-fiber casting solution on a horizontally placed mesh to form a film; (2) immediately putting the membrane obtained in the step (1) into a 0.1-30 g/L sodium sulfanilate aqueous solution for phase conversion, transferring the membrane into a newly configured catalyst solution after the phase conversion is finished, sealing the membrane to perform an amide dehydration condensation reaction, wherein the catalyst solution is a mixed aqueous solution of 0.1-5 g/L1-ethyl-3- (3-dimethylamine-nitrosyl) carbodiimide hydrochloride and 0.05-3 g/L LN-hydroxysuccinimide, and drying the membrane after full reaction to obtain the cation exchange membrane. The preparation process is simple and convenient, the operation is easy, and the preparation method is non-toxic and environment-friendly; the prepared cation exchange membrane has good tolerance performance to organic solvents.
Description
Technical Field
The invention relates to a preparation method of an organic solvent resistant cation exchange membrane.
Technical Field
With the rapid development of society, water pollution and water resource shortage have become the most urgent global problems, and the sustainable development of human beings is directly restricted. In particular, agricultural wastewater and industrial wastewater have been receiving attention because they contain a large amount of harmful metal ions and other compounds which are difficult to treat. Currently, ion exchange membranes are used as the core component of electrodialysis, and the treatment of salt removal in the desalination direction of water treatment has irreplaceable advantages. But the traditional cation exchange membrane material cannot meet the metal salt ion removal of the current complex water environment. Especially in the aqueous solution mixed with a large amount of organic solvent, the ion exchange membrane material is chemically degraded, the ion exchange capacity is reduced, and the ion desalting performance is greatly influenced. Therefore, finding and designing suitable membrane materials for organic solvent cation exchange membranes has become an urgent research hotspot. The discovery opens up a wide application prospect for applying the cation exchange membrane to the metal ion removal treatment of the sewage mixed with the organic solvent at present.
The Kevlar aramid material synthesized by the poly dimethyl terephthalate (PPTA) has excellent tolerance to the most common organic solvent due to the highly ordered and asymmetric alternating structure of long molecular chains and intermolecular hydrogen bonds, thereby having extremely high application prospect. The industrial aramid product is dissolved in a mixed solution of dimethyl sulfoxide and potassium hydroxide, and provides an ideal material basis for designing an organic solvent-resistant ion exchange membrane.
Disclosure of Invention
The invention aims to provide a preparation method of an organic solvent resistant cation exchange membrane.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method of making a cation exchange membrane, the method comprising:
(1) the Kevlar aramid material, potassium hydroxide and a dimethyl sulfoxide solvent are mixed according to the mass percentage of 0.1-5%: 0.5% -10%: 85% -99% (the sum of the weight of Kevlar aramid fiber material, potassium hydroxide and dimethyl sulfoxide solvent is 100%), sealing and stirring to perform amide partial hydrolysis reaction, dissolving the Kevlar aramid fiber material into nanofiber membrane casting solution with amino, and scraping the nanofiber membrane casting solution on a horizontally placed mesh to form a membrane;
(2) immediately putting the membrane obtained in the step (1) into a 0.1-30 g/L sodium sulfanilate aqueous solution for phase conversion, transferring the membrane into a newly configured catalyst solution after the phase conversion is finished, sealing the membrane to perform an amide dehydration condensation reaction, wherein the catalyst solution is a mixed aqueous solution of 1-ethyl-3- (3-dimethylamine-nitrosyl) carbodiimide hydrochloride and N-hydroxysuccinimide, the concentrations of the 1-ethyl-3- (3-dimethylamine-nitrosyl) carbodiimide hydrochloride and the N-hydroxysuccinimide in the mixed solution are respectively 0.1-5 g/L and 0.05-3 g/L, and drying the membrane after full reaction to obtain the cation exchange membrane.
In the invention, the Kevlar aramid fiber material can be aramid nanofiber with models of AP, K29, K49, 100, 119, 129, KM2, KM2Plus and the like.
Preferably, in the step (1), the Kevlar aramid material, the potassium hydroxide and the dimethyl sulfoxide solvent are mixed according to the mass percentage of 0.5-5%: 1% -10%: 85% to 98%, more preferably 1% to 3%: 3% -7%: 90 to 96 percent.
Preferably, in step (1), the amide partial hydrolysis reaction conditions are: the reaction temperature is 20-90 ℃, and the reaction time is 3-7 days. As a further preference, the conditions of the amide partial hydrolysis reaction are: the mixture is stirred and reacted for 2 to 4 days at the temperature of between 40 and 90 ℃, and then the temperature is reduced to between 20 and 30 ℃ for reaction for 1 to 3 days.
Preferably, in the step (1), the conditions for scraping the film are as follows: the temperature is 0-40 ℃, the humidity is 4-40%, and the thickness of the film scraping knife is 50-500 mu m; more preferred knifing conditions are: the temperature was 20 ℃, the humidity was 20%, and the thickness of the doctor blade was 250 μm.
Preferably, in step (2), the concentration of the sodium sulfanilate aqueous solution is 1 to 6g/L, and most preferably 6 g/L.
Preferably, in step (2), the phase inversion time is 10-20min, more preferably 15 min.
Preferably, in the step (2), the amide dehydration reaction conditions are as follows: soaking at room temperature for 10-20 days.
Preferably, in the step (2), the drying temperature is 40 to 70 ℃.
Compared with the prior art, the invention has the beneficial effects that: the preparation process is simple and convenient, the operation is easy, and the preparation method is non-toxic and environment-friendly; the prepared cation exchange membrane has good tolerance performance to organic solvents.
Drawings
Fig. 1 shows the membrane ion exchange capacity of the prepared cation exchange membrane, and it can be seen that the membrane ion exchange capacity is improved along with the increase of the dosage of the sodium sulfanilate.
Fig. 2 shows the water content of the prepared cation exchange membrane, and it can be seen that the water content of the membrane is firstly reduced and then improved along with the increase of the dosage of the sodium sulfanilate.
Fig. 3 is a film surface resistance of the prepared cation exchange membrane, and it can be seen that the membrane ion exchange capacity is reduced along with the increase of the dosage of the sodium sulfanilate.
FIG. 4 is a scanning electron micrograph of the cation exchange membrane prepared.
FIG. 5 is a plot of polarization current versus voltage for the prepared K-CEM-0 in 0.1M NaCl.
FIG. 6 is a plot of polarization current versus voltage for the prepared K-CEM-1 in 0.1M NaCl.
Fig. 7 is a schematic view of an electrodialysis unit.
FIG. 8 shows that the effective membrane area of K-CEM-1 membrane is 20cm at 15.0V
2Desalting chamber in the lower desalting chamber.
FIG. 9 is a plot of polarization current versus voltage for the prepared K-CEM-2 in 0.1M NaCl.
FIG. 10 shows K-CEM-2 films at 15.0V withThe effective membrane area is 20cm
2Desalting chamber in the lower desalting chamber.
FIG. 11 is a plot of polarization current versus voltage for the prepared K-CEM-3 in 0.1M NaCl.
FIG. 12 shows that the effective membrane area of K-CEM-3 membrane is 20cm at 15.0V
2Desalting chamber in the lower desalting chamber.
FIG. 13 shows the desalination of electrodialysis desalination and concentration compartment after soaking K-CEM-3 membrane in 25% acetone aqueous solution for 48 hours.
FIG. 14 shows the desalination of electrodialysis desalination chamber and concentration chamber after soaking K-CEM-3 membrane in 50% acetone aqueous solution for 48 hr.
FIG. 15 shows the desalination of electrodialysis desalination and concentration desalination of K-CEM-3 membrane in 75% acetone solution after soaking in water for 48 hr.
FIG. 16 shows the desalination of electrodialysis desalination chamber and concentration chamber after soaking K-CEM-3 membrane in 100% acetone for 48 hours.
Detailed Description
The invention is described in further detail below with reference to the following figures and embodiments:
example 1:
weighing 1g of Kevlar aramid fiber material (Kevlar K29 type, Dupont, USA), 2.5g of potassium hydroxide and 51.5g of dimethyl sulfoxide solvent, mixing, adding into a 250mL three-neck flask, and sealing; the three-neck flask is put into an oil bath pot, the temperature of the oil bath pot is controlled to be 50 ℃, and the magnetic stirring speed is started to be 500 rpm. After 96h, the oil bath temperature was adjusted to 20 ℃ and the magnetic stirring was turned off. And after 48h, taking the dried glass plate, fixing the mesh, placing the glass plate in a horizontal constant-temperature and constant-humidity control operation box, adjusting the temperature of the control operation box to be 20 ℃, the humidity to be 20 percent, and the thickness of a film scraping knife to be 250 mu m, and scraping the film on the mesh with the thickness of 40cm by 20 cm. The newly obtained film was immersed in 2L of a mixed aqueous solution of 1 g/L1-ethyl-3- (3-dimethylamine-nitrosyl) carbodiimide hydrochloride and 0.6g/L LN-hydroxysuccinimide and sealed. After soaking for 15 days, flatly placing the membrane into a blast drying oven, setting the temperature at 70 ℃, and taking out the membrane after 12 hours, thereby obtaining the dry cation exchange membrane with high temperature resistance and organic solvent resistance and named as K-CEM-0.
In FIG. 1, a is the membrane ion exchange capacity of the prepared K-CEM-0, in FIG. 2, a is the membrane water content of the prepared K-CEM-0, in FIG. 3, a is the membrane area resistance of the prepared K-CEM-0, and in FIG. 4, a is the scanning electron microscope image of the prepared K-CEM-0. The polarization current-voltage curve in 0.1M NaCl was determined as shown in FIG. 5.
Example 2:
weighing 1g of Kevlar aramid material, 2.5g of potassium hydroxide and 51.5g of dimethyl sulfoxide solvent, mixing, adding into a 250mL three-neck flask, and sealing; the three-neck flask is put into an oil bath pot, the temperature of the oil bath pot is controlled to be 50 ℃, and the magnetic stirring speed is started to be 500 rpm. After 96h, the oil bath temperature was adjusted to 20 ℃ and the magnetic stirring was turned off. And after 48 hours, taking the dried glass plate, fixing a 40 cm-20 cm mesh, placing the glass plate in a horizontal constant-temperature and constant-humidity control operation box, adjusting the temperature of the control operation box to be 20 ℃, the humidity to be 20 percent, the thickness of a film scraping knife to be 250 mu m, and scraping the film on the 40 cm-20 cm mesh. The newly obtained membrane is immediately immersed into 2L of 1g/L sodium sulfanilate aqueous solution for phase conversion process. After the phase inversion (15min) was completed, the reaction mixture was transferred to a newly prepared solution and sealed in 2L of a catalyst solution of 0.5 g/L1-ethyl-3- (3-dimethylamine-nitrosyl) carbodiimide hydrochloride and 0.3g/L LN-hydroxysuccinimide to perform an amide dehydration condensation reaction. After 15 days, the membrane is flatly placed in a blast drying oven, the temperature is set to be 70 ℃, and the membrane is taken out after 12 hours, so that the dry cation exchange membrane with high temperature resistance and organic solvent resistance is obtained and named as K-CEM-1.
B in FIG. 1 is the membrane ion exchange capacity of the prepared K-CEM-0, b in FIG. 2 is the membrane water content of the prepared K-CEM-1, b in FIG. 3 is the membrane area resistance of the prepared K-CEM-1, and b in FIG. 4 is the membrane scanning electron microscope image of the prepared K-CEM-1.
The polarization current-voltage curve in 0.1M NaCl was measured to obtain the polarization performance characteristics of the membrane in 0.1M NaCl (FIG. 6). In electrodialysis (both the anode and cathode were ruthenium iridium electrode plates, and the anion exchange membrane was an AEM-Type I homogeneous anion exchange membrane manufactured by Fujifilm corporation of Japan, and the effective membrane area was 20 cm) as shown in FIG. 7
2) In (1), determination of K-CEM-1 filmThe desalination chamber desalination at 15.0V resulted in the results shown in fig. 8.
Example 3:
a cation exchange membrane was prepared by following the same procedure as in example 2 except that a 1g/L sodium sulfanilate solution was changed to a 4g/L sodium sulfanilate solution, and the resulting membrane was named K-CEM-2.
In FIG. 1, c is the membrane ion exchange capacity of the prepared K-CEM-2, in FIG. 2, c is the membrane water content of the prepared K-CEM-2, in FIG. 3, c is the membrane area resistance of the prepared K-CEM-2, and in FIG. 4, c is the membrane scanning electron microscope image of the prepared K-CEM-2.
The polarization current-voltage curve in 0.1M NaCl was measured to obtain the polarization performance characteristics of the membrane in 0.1M NaCl (FIG. 9). In electrodialysis (both the anode and cathode were ruthenium iridium electrode plates, and the anion exchange membrane was an AEM-Type I homogeneous anion exchange membrane manufactured by Fujifilm corporation of Japan, and the effective membrane area was 20 cm) as shown in FIG. 7
2) The desalting of the desalting chamber of the K-CEM-2 membrane at a voltage of 15.0V was measured, and the results are shown in FIG. 10.
Example 4:
according to the same procedure as in example 2, only 1g/L sodium sulfanilate solution was changed to 6g/L sodium sulfanilate solution, and the resulting membrane was named K-CEM-3.
D in FIG. 1 is the membrane ion exchange capacity of the prepared K-CEM-3, d in FIG. 2 is the membrane water content of the prepared K-CEM-3, d in FIG. 3 is the membrane area resistance of the prepared K-CEM-3, and d in FIG. 4 is the membrane scanning electron microscope image of the prepared K-CEM-3.
The polarization current-voltage curve in 0.1M NaCl was measured to obtain the polarization performance characteristics of the membrane in 0.1M NaCl (FIG. 11). In electrodialysis (both the anode and cathode were ruthenium iridium electrode plates, and the anion exchange membrane was an AEM-Type I homogeneous anion exchange membrane manufactured by Fujifilm corporation of Japan, and the effective membrane area was 20 cm) as shown in FIG. 7
2) The desalting of the desalting chamber of the K-CEM-3 membrane at a voltage of 15.0V was measured, and the results are shown in FIG. 12.
Example 5:
a K-CEM-3 membrane was selected and soaked in 25% aqueous acetone for 48 hours. Then the mixture is put inThe membrane was placed in an electrodialysis apparatus (as shown in FIG. 7, the cathode and anode were ruthenium iridium electrode plates, the anion exchange membrane was an AEM-Type I homogeneous anion exchange membrane manufactured by Fujifilm corporation of Japan, and the effective membrane area was 20cm
215V applied voltage), and the ion (Na) was measured
2SO
4) The conductivity changes in the rich and weak chambers, and the results are shown in (a) and (b) of fig. 13.
Example 6:
a K-CEM-3 membrane was selected and soaked in 50% aqueous acetone for 48 hours. Then, the membrane was placed in an electrodialysis apparatus (as shown in FIG. 7, the cathode and anode were ruthenium iridium electrode plates, the anion exchange membrane was an AEM-Type I homogeneous anion exchange membrane manufactured by Fujifilm corporation of Japan, and the effective membrane area was 20cm
215V applied voltage), and the ion (Na) was measured
2SO
4) The conductivity changes in the rich and weak chambers, and the results are shown in (a) and (b) of fig. 14.
Example 7:
a K-CEM-3 membrane was selected and soaked in 75% aqueous acetone for 48 hours. Then, the membrane was placed in an electrodialysis apparatus (as shown in FIG. 7, the cathode and anode were ruthenium iridium electrode plates, the anion exchange membrane was an AEM-Type I homogeneous anion exchange membrane manufactured by Fujifilm corporation of Japan, and the effective membrane area was 20cm
215V applied voltage), and the ion (Na) was measured
2SO
4) The conductivity changes in the rich and weak chambers, and the results are shown in (a) and (b) of fig. 15.
Example 7:
a K-CEM-3 membrane was selected and soaked in 100% acetone for 48 hours. Then, the membrane was placed in an electrodialysis apparatus (as shown in FIG. 7, the cathode and anode were ruthenium iridium electrode plates, the anion exchange membrane was an AEM-Type I homogeneous anion exchange membrane manufactured by Fujifilm corporation of Japan, and the effective membrane area was 20cm
215V applied voltage), and the ion (Na) was measured
2SO
4) The conductivity changes in the rich and weak chambers, and the results are shown in (a) and (b) of fig. 16.
Claims (10)
1. A method of making a cation exchange membrane, the method comprising:
(1) the Kevlar aramid material, potassium hydroxide and a dimethyl sulfoxide solvent are mixed according to the mass percentage of 0.1-5%: 0.5% -10%: 85 to 99 percent of the mixture is mixed, sealed and stirred to carry out amide partial hydrolysis reaction, the Kevlar aramid fiber material is dissolved into nano-fiber casting solution with amino, and the nano-fiber casting solution is scraped into a film on a horizontally placed mesh;
(2) immediately putting the membrane obtained in the step (1) into a 0.1-30 g/L sodium sulfanilate aqueous solution for phase conversion, transferring the membrane into a newly configured catalyst solution after the phase conversion is finished, sealing the membrane to perform an amide dehydration condensation reaction, wherein the catalyst solution is a mixed aqueous solution of 1-ethyl-3- (3-dimethylamine-nitrosyl) carbodiimide hydrochloride and N-hydroxysuccinimide, the concentrations of the 1-ethyl-3- (3-dimethylamine-nitrosyl) carbodiimide hydrochloride and the N-hydroxysuccinimide in the mixed solution are respectively 0.1-5 g/L and 0.05-3 g/L, and drying the membrane after full reaction to obtain the cation exchange membrane.
2. The method of claim 1, wherein: in the step (1), the Kevlar aramid material, the potassium hydroxide and the dimethyl sulfoxide solvent are respectively 0.5-5 percent, 1-10 percent and 85-98 percent in percentage by mass.
3. The method of claim 1, wherein: in the step (1), the mass percentages of the Kevlar aramid fiber material, the potassium hydroxide and the dimethyl sulfoxide solvent are respectively 1-3%, 3-7% and 90-96%.
4. The method according to any one of claims 1 to 3, wherein: in the step (1), the conditions of the amide partial hydrolysis reaction are as follows: the reaction temperature is 20-90 ℃, and the reaction time is 3-7 days.
5. The method of claim 4, wherein: the conditions for the amide partial hydrolysis reaction are: the mixture is stirred and reacted for 2 to 4 days at the temperature of between 40 and 90 ℃, and then the temperature is reduced to between 20 and 30 ℃ for reaction for 1 to 3 days.
6. The method according to any one of claims 1 to 3, wherein: in the step (1), the conditions for scraping the film are as follows: the temperature is 0-40 ℃, the humidity is 4-40%, the thickness of the film scraping knife is 50-500 mu m, and the preferable film scraping conditions are as follows: the temperature was 20 ℃, the humidity was 20%, and the thickness of the doctor blade was 250 μm.
7. The method according to any one of claims 1 to 3, wherein: in the step (2), the concentration of the sodium sulfanilate aqueous solution is 1-6g/L, and the most preferable concentration is 6 g/L.
8. The method according to any one of claims 1 to 3, wherein: in the step (2), the phase inversion time is 10-20min, more preferably 15 min.
9. The method according to any one of claims 1 to 3, wherein: in the step (2), the amide dehydration reaction conditions are as follows: soaking at room temperature for 10-20 days.
10. The method according to any one of claims 1 to 3, wherein: in the step (2), the drying temperature is 40-70 ℃.
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Citations (5)
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|---|---|---|---|---|
| US20040014960A1 (en) * | 2000-10-10 | 2004-01-22 | Tae-Seok Moon | Crosslinked amide derivatives of hyaluronic acid and manufacturing method thereof |
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| CN107308824A (en) * | 2017-08-25 | 2017-11-03 | 南开大学 | A kind of preparation method of sulfonic acid type cation exchange membrane |
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2019
- 2019-09-16 CN CN201910870632.6A patent/CN110773241A/en active Pending
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| US20040014960A1 (en) * | 2000-10-10 | 2004-01-22 | Tae-Seok Moon | Crosslinked amide derivatives of hyaluronic acid and manufacturing method thereof |
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Application publication date: 20200211 |