CN110684158A - Permanent antibacterial polyether sulfone membrane material and preparation method thereof - Google Patents
Permanent antibacterial polyether sulfone membrane material and preparation method thereof Download PDFInfo
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
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- C—CHEMISTRY; METALLURGY
- 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
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- C—CHEMISTRY; METALLURGY
- 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
- C08J2351/00—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
- C08J2351/08—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
Abstract
The invention discloses a permanent antibacterial polyether sulfone membrane material and a preparation method thereof. According to the invention, through a chemical modification method of Co-gamma radiation grafting, ionic liquid containing unsaturated bonds and connected by chemical bonds is uniformly distributed on the surface of polyether sulfone; the mass ratio of the ionic liquid to the polyether sulfone is 2-11: 100, respectively; the above method is through the radiation irradiation, the ionic liquid of blending the flat membrane is connected to the polymer through the chemical bond. Because the polymer and the ionic liquid have good compatibility, the ionic liquid micromolecules can be fully contacted with the polymer during radiation irradiation, so that the ionic liquid micromolecules are grafted to a PES molecular chain.
Description
Technical Field
The invention relates to a permanent antibacterial polyether sulfone membrane material and a preparation method thereof, in particular to a polymer composite material with ionic liquid uniformly distributed on the surface of the material and connected through chemical bonds and a preparation method thereof.
Background
The polymer membrane material has wide application in the fields of sanitation, medical treatment, biology, water treatment and the like, and is generally prepared from membrane materials such as polyester, polysulfone, polyvinylidene fluoride, polyurethane and the like. The invention mainly adopts commercial polyether sulfone (PES) as a membrane material, mainly because PES has better thermal stability, excellent mechanical property and chemical corrosion resistance, and PES and PVDF and the like have certain difference and are amorphous polymers, the influence caused by a crystallization process does not need to be considered in the process of membrane formation, and the PES is completely a porous membrane formed by liquid-liquid phase separation.
However, since PES membrane materials are hydrophobic, researchers have been developing PES membrane materials modified to obtain hydrophilic PES membrane materials in order to solve the problems of hydrophilicity, antifouling property, antibacterial property, and the like of PES membrane materials. However, the existing modification methods face a number of problems: 1. the modified material has the problems of non-uniformity and instability of performance; 2. high cost, environmental pollution and the like; therefore, the invention mainly relates to a long-term stable modification method of radiation grafting ionic liquid. Irradiation grafting can be mainly divided into electron beam irradiation and Co-gamma irradiation according to a radiation source, the electron beam irradiation stability is good, but the irradiation energy is too small to meet the grafting condition of partial polymers, so that the Co-gamma irradiation is selected to graft the ionic liquid after the influence of different radiation sources on the irradiation grafting of PES is researched.
Ionic Liquid (IL) is a substance that is Liquid at room temperature and is composed of ions, and is called a "green solvent" because it has the advantages of good compatibility with polymers, good hydrophilicity, and thermodynamic stability.
The invention mainly comprises the ionic liquid which is uniformly distributed on the surface (inner surface and outer surface) of the PES film material and is connected by chemical bonds, so that a good modification effect can be achieved, and meanwhile, the ionic liquid and the polymer are connected by the chemical bonds, so that the material has permanent antibacterial and antifouling effects.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provide a permanent antibacterial polyether sulfone film material.
According to the invention, by a chemical modification method of Co-gamma radiation grafting, the ionic liquid connected with chemical bonds is uniformly distributed on the surface of the polymer material, and the grafted ionic liquid has excellent performance, so that the material can stably maintain a good modification effect for a long time.
The polymer membrane material is polyether sulfone and has the following structural formula:
the Ionic Liquid (IL) is an ionic liquid containing unsaturated bonds; preferably, the ionic liquid containing unsaturated bonds is imidazole ionic liquid, and the imidazole ionic liquid has better hydrophilicity and antibacterial property and can play a better modifying role on polyether sulfone; wherein the cation has the following structural formula:
wherein R1 is C1-C24 alkyl or C2-C24 alkenyl; r2 is alkenyl containing C2-C24; the anion of the ionic liquid is PF6 -、BF4 -、Br-、Cl-、I-、NO3 -、CF3CO2 -、CH3COO-、(CF3SO3)2N-；
Wherein the mass ratio of the Ionic Liquid (IL) to the polymer is 2-11: 100, respectively;
the invention also aims to provide a preparation method of the permanent antibacterial PES film material.
The method comprises the following steps:
adding PES and ionic liquid into a reaction kettle according to a certain proportion to carry out solution blending; the mass ratio of the Ionic Liquid (IL) to the PES is 2-11: 100. the temperature is set to be 60 ℃ in the solution blending process, and N, N-Dimethylformamide (DMF) is selected as a solvent.
The Ionic Liquid (IL) is an ionic liquid containing unsaturated bonds; preferably, the ionic liquid containing unsaturated bonds is imidazole ionic liquid.
Step (2), spreading a film on the solution after the solution blending, and drying to remove the solvent to obtain a polymer and ionic liquid blended film;
step (3), placing the obtained blend film in a polyethylene plastic bag for radiation irradiation;
the irradiation is Co-gamma ray irradiation, and the experimental conditions are normal temperature and vacuum environment;
the irradiation absorbed dose is 30 kGy;
and (4) directly pressing and molding the grafted blend obtained by irradiation.
Performing soxhlet extraction on the irradiated blend membrane with methanol, and analyzing the structures and performances of the blend membrane, such as grafting rate, grafting sites and the like;
the step (3) of the method is that the ionic liquid of the blended flat membrane is connected to the polymer through a chemical bond by irradiation of radiation. Because the polymer and the ionic liquid have good compatibility, the ionic liquid micromolecules can be fully contacted with the polymer during radiation irradiation, so that the ionic liquid micromolecules are grafted to a PES molecular chain.
The preparation method only needs common solution blending equipment, the industrial preparation is simple, and the equipment required by the radiation is a common radiation source;
the invention has the beneficial effects that:
the modified PES membrane material disclosed by the invention has excellent antibacterial property and hydrophilicity, the preparation process is green and environment-friendly, the cost is low, and the ionic liquid is selected as an additive to accord with the principle of green chemistry.
The reason for selecting ionic liquids according to the invention is as follows: (1) the ionic liquid consists of anions and cations, exists in a liquid form at normal temperature, has extremely low vapor pressure, is not easy to volatilize, and is a good green solvent; (2) anions and cations of the ionic liquid can play a good role in sterilization, and the ionic liquid is a high-efficiency green antibacterial agent; (3) the ionic liquid has good electrochemical and thermal stability, so that the ionic liquid can be used at a higher temperature, and the application range of the material is enlarged; (4) the sterilization and bacteriostasis mechanism of the ionic liquid is as follows: the cell wall surface of bacterium is electronegativity usually, and ionic liquid's positive ion takes place to contact through the cell wall of electrostatic interaction and bacterium, makes the cell wall of bacterium take place to warp to destroy the structure of bacterium, make the inside metabolism of bacterium normally go on, finally kill the bacterium, reach and disinfect and antibacterial effect.
The reason for using chemical bonds to connect ionic liquids in the present invention is as follows: the traditional polymer material modified by common physical blending loses performance and pollutes the surrounding environment with time in the long-term use process; the invention realizes the connection of the ionic liquid and the polymer PES molecules through chemical bonds, avoids the loss of the ionic liquid caused by migration and other reasons in the long-term use process, and has long-term and stable modification effect of the material.
Drawings
FIGS. 1(1) - (4) are SEM images for example 1(2 wt% IL-PES modified membrane), example 2(4 wt% IL-PES modified membrane), example 3(6 wt% IL-PES modified membrane), example 4(10 wt% IL-PES modified membrane), and FIG. 1(5) is a SEM image for comparative example 1 (pure PES membrane), respectively;
FIG. 2(1) - (3) shows example 4(10 wt% IL-PES modified membrane) with Co-. gamma.as the radiation source; comparative example 1 (pure PES membrane); comparative example 2(10 wt% -PES-e-beam modified membrane) the radiation source was e-beam; 1H-NMR spectrum of comparative example 3 (pure ionic liquid IL).
Detailed Description
The present invention is described in detail below with reference to the attached drawings and the embodiments, but the present invention is not limited to the scope of the embodiments.
The polymer grafted by the Ionic Liquid (IL) is obtained by irradiating a PES and IL blending modified membrane by Co-gamma radiation. After Co-gamma irradiation, the double bonds of the ionic liquid are opened and grafted to the polymer molecular chain to obtain the graft polymer.
The polymer is polyether sulfone and has good thermal stability and mechanical property.
The above IL is preferably an ionic liquid having an unsaturated bond. More preferably, the ionic liquid is imidazole ionic liquid, and the structure of the ionic liquid is as follows:
wherein R1 is C1-C24 alkyl or C2-C24 alkenyl; r2 is alkenyl containing C2-C24; the anion in the ionic liquid is PF6 -、BF4 -、Br-、Cl-、I-、NO3 -、CF3CO2 -、CH3COO-Or (CF)3SO3)2N-；
Wherein the ionic liquid accounts for 2-11% of the PES matrix by mass.
Wherein the irradiation is Co-gamma irradiation.
Wherein the absorbed dose of the irradiation is 30 kGy.
Wherein the experimental conditions during irradiation are normal temperature, air and nitrogen.
The specific process of the invention is as follows:
firstly, adding PES and ionic liquid into a reaction kettle according to a certain proportion, taking DMF as a solvent, and carrying out solution blending for 6 hours at 60 ℃. Then, cooling the solution to room temperature, pouring the solution into a PTFE mold for film paving, volatilizing the solvent of the obtained film, drying the film for 24 hours in vacuum, and irradiating the film at room temperature under the irradiation dose of 30kGy to finally obtain the modified film of the ionic liquid and the PES.
And secondly, soxhlet extracting the PES modified membrane subjected to radiation irradiation for 24h by using methanol, vacuum drying for 24h, and finally analyzing the grafting rate and the grafting sites by means of nuclear magnetism and the like.
The present invention will be described in detail below.
In this example and in the comparative examples, the polymer PES was used as matrix, produced by Basff and having the model number ULTRASON E6020P.
The imidazole-based ionic liquid containing unsaturated bonds used in the present example was: 1-vinyl-3-butylimidazolium tetrafluoroborate.
Example 1
Firstly, adding 9.8g of PES and 0.2g of 1-vinyl-3-butylimidazole tetrafluoroborate into a reaction kettle, and blending the solution for 6 hours at the temperature of 60 ℃; and then, cooling the solution to room temperature, pouring the solution into a PTFE (polytetrafluoroethylene) mold for film paving, volatilizing the solvent of the obtained film, and drying the film for 24 hours in vacuum to finally obtain the blend film grafted with the ionic liquid. Noted as 2 wt% to PES modified membrane.
And (2) placing the 2 wt% -PES modified membrane into a self-sealing bag made of polyethylene. In Co-gamma irradiation, normal temperature irradiation was performed at an irradiation dose of 30 kGy.
And (3) directly pressing and molding the graft blend obtained by irradiation to obtain a PES modified membrane, wherein the molding temperature is 250 ℃, the pressure is 10MPa, the pressure is maintained for 3min, and the thickness is 300 microns.
Example 2
Firstly, adding 9.6g of PES and 0.4g of 1-vinyl-3-butylimidazole tetrafluoroborate into a reaction kettle, and blending the solution for 6 hours at the temperature of 60 ℃; and then, cooling the solution to room temperature, pouring the solution into a PTFE (polytetrafluoroethylene) mold for film paving, volatilizing the solvent of the obtained film, and drying the film for 24 hours in vacuum to finally obtain the blend film grafted with the ionic liquid. Recorded as 4 wt% to PES modified membrane.
And (2) placing the 4 wt% -PES modified membrane into a self-sealing bag made of polyethylene. In Co-gamma irradiation, normal temperature irradiation was performed at an irradiation dose of 30 kGy.
And (3) directly pressing and molding the graft blend obtained by irradiation to obtain a PES modified membrane, wherein the molding temperature is 250 ℃, the pressure is 10MPa, the pressure is maintained for 3min, and the thickness is 300 microns.
Example 3
Firstly, adding 9.4g of PES and 0.6g of 1-vinyl-3-butylimidazole tetrafluoroborate into a reaction kettle, and blending the solution for 6 hours at the temperature of 60 ℃; and then, cooling the solution to room temperature, pouring the solution into a PTFE (polytetrafluoroethylene) mold for film paving, volatilizing the solvent of the obtained film, and drying the film for 24 hours in vacuum to finally obtain the blend film grafted with the ionic liquid. Recorded as 6 wt% to PES modified membrane.
And (2) placing the 6 wt% -PES modified membrane into a self-sealing bag made of polyethylene. In Co-gamma irradiation, normal temperature irradiation was performed at an irradiation dose of 30 kGy.
And (3) directly pressing and molding the graft blend obtained by irradiation to obtain a PES modified membrane, wherein the molding temperature is 250 ℃, the pressure is 10MPa, the pressure is maintained for 3min, and the thickness is 300 microns.
Example 4
Firstly, adding 9.0g of PES and 1.0g of 1-vinyl-3-butylimidazole tetrafluoroborate into a reaction kettle, and blending the solution for 6 hours at the temperature of 60 ℃; and then, cooling the solution to room temperature, pouring the solution into a PTFE (polytetrafluoroethylene) mold for film paving, volatilizing the solvent of the obtained film, and drying the film for 24 hours in vacuum to finally obtain the blend film grafted with the ionic liquid. Recorded as 10 wt% PES modified membrane.
And (2) placing the 10 wt% -PES modified membrane into a self-sealing bag made of polyethylene. In Co-gamma irradiation, normal temperature irradiation was performed at an irradiation dose of 30 kGy.
And (3) directly pressing and molding the graft blend obtained by irradiation to obtain a PES modified membrane, wherein the molding temperature is 250 ℃, the pressure is 10MPa, the pressure is maintained for 3min, and the thickness is 300 microns.
Comparative example 1
PES is dried in a vacuum drying oven at 80 ℃ overnight, 10.0g of PES is weighed and added into a reaction kettle, the temperature is 60 ℃, and the solution is blended for 6 hours; then, the solution is cooled to room temperature, poured into a PTFE mold for film paving, the obtained film is subjected to solvent volatilization, and vacuum drying is carried out for 24 hours, so that the pure PES film is finally obtained. As pure PES membrane.
And (3) directly pressing and forming the pure PES film obtained by film laying to obtain the PES film, wherein the forming temperature is 250 ℃, the pressure is 10MPa, the pressure is maintained for 3min, and the thickness is 300 micrometers.
Comparative example 2
Firstly, adding 9.0g of PES and 1.0g of 1-vinyl-3-butylimidazole tetrafluoroborate into a reaction kettle, and blending the solution for 6 hours at the temperature of 60 ℃; and then, cooling the solution to room temperature, pouring the solution into a PTFE (polytetrafluoroethylene) mold for film paving, volatilizing the solvent of the obtained film, and drying the film for 24 hours in vacuum to finally obtain the blend film grafted with the ionic liquid.
And (2) placing the 10 wt% -PES modified membrane into a self-sealing bag made of polyethylene. Taking an electron beam as a radiation source, carrying out normal-temperature radiation under the irradiation dose of 30kGy, and marking as 10 wt% -PES-electron beam modified membrane.
And (3) directly pressing and molding the graft blend obtained by irradiation to obtain a PES modified membrane, wherein the molding temperature is 250 ℃, the pressure is 10MPa, the pressure is maintained for 3min, and the thickness is 300 microns.
Comparative example 3
Comparative example 3 is pure 1-vinyl-3-butylimidazolium tetrafluoroborate.
As shown in FIG. 1, SEM analysis of example 1(2 wt% IL-PES modified membrane), example 2(4 wt% IL-PES modified membrane), example 3(6 wt% IL-PES modified membrane), example 4(10 wt% IL-PES modified membrane) and comparative example (pure PES membrane) shows that PES has better compatibility with ionic liquid IL, and as the content of ionic liquid is increased, no phase region is seen on the SEM picture, indicating that the two are compatible.
As shown in FIG. 2, for example 4(10 wt% IL-PES modified membrane), comparative example 1 (pure PES membrane), comparative example 2(10 wt% PES-E-beam modified membrane) and comparative example 3 (pure ionic liquid IL)1H-NMR spectrum, we can conclude that: 1. we could not find the characteristic peak about ionic liquid on the nuclear magnetic map of 10 wt% -PES-electron beam modified film, because we believe that ionic liquid could not be grafted to PES molecular chain mainly due to too low energy of electron beam radiation. 2. Even under the condition of constant methanol washing, the methyl and methylene peaks of the ionic liquid still appear at 1.86ppm and 0.9ppm of the membrane grafted with the ionic liquid, so that the ionic liquid is considered to be grafted, and a new peak appears near the hydrogen on the benzene ring at 8.3ppm, so that the ionic liquid is considered to be grafted on the benzene ring. 3. We confirmed that the ionic liquid had been grafted not only on the PES molecular chain, but also on the benzene ring of the molecular chain. Therefore, the chemical modification method successfully and stably distributes the ionic liquid in the PES matrix in a chemical bond mode for a long time by a green and environment-friendly chemical means.
As shown in Table 1, the graft ratio of the PES-modified membranes was measured for each of the examples (PES-modified membranes having different ionic liquid contents). And removing the non-grafted ionic liquid by Soxhlet extraction of methanol, calculating the mass difference before and after extraction, and finally obtaining the grafting rate and the grafting efficiency of each embodiment. This indicates that the ionic liquid immobilized on the polymer by irradiation is not lost with washing and impregnation with methanol solvent and remains in the polymer PES matrix.
Table 1 shows the determination of the grafting yield of the examples (PES-modified membranes with different ionic liquid contents)
The above embodiments are not intended to limit the present invention, and the present invention is not limited to the above embodiments, and all embodiments are within the scope of the present invention as long as the requirements of the present invention are met.
Claims (6)
1. A permanent antibacterial polyethersulfone membrane material is characterized in that ionic liquid connected with chemical bonds is uniformly distributed on the surface of the polyethersulfone material by a chemical modification method of Co-gamma radiation grafting; the mass ratio of the ionic liquid to the polymer is 2-11: 100, respectively;
the ionic liquid is an ionic liquid containing unsaturated bonds.
2. A preparation method of a permanent antibacterial polyether sulfone membrane material is characterized by comprising the following steps:
adding PES and ionic liquid into a reaction kettle according to a certain proportion to carry out solution blending; wherein the mass ratio of the ionic liquid to the PES is 2-11: 100, respectively;
the ionic liquid is an ionic liquid containing unsaturated bonds;
step (2), spreading a film on the solution after the solution blending, and drying to remove the solvent to obtain a polymer and ionic liquid blended film;
step (3), placing the obtained blend film in a polyethylene plastic bag for radiation irradiation;
the irradiation is Co-gamma ray irradiation, and the experimental conditions are normal temperature and vacuum environment;
and (4) directly pressing and molding the grafted blend obtained by irradiation.
3. The permanent antibacterial polyethersulfone membrane material according to claim 1 or the permanent antibacterial polyethersulfone membrane material obtained by the preparation method according to claim 2, characterized in that the ionic liquid containing unsaturated bonds is imidazole ionic liquid;
the cation structural formula is as follows:
wherein R1 is C1-C24 alkyl or C2-C24 alkenyl; r2 is alkenyl containing C2-C24;
the anion is PF6 -、BF4 -、Br-、Cl-、I-、NO3 -、CF3CO2 -、CH3COO-Or (CF)3SO3)2N-。
4. A permanent antibacterial polyethersulfone film material according to claim 1 or obtained by the preparation method according to claim 2, characterized in that the Co-gamma irradiation absorption dose is 30 kGy.
5. The method for preparing a permanent antibacterial polyethersulfone film material as claimed in claim 2, wherein the temperature in the solution blending process in step (1) is 60 ℃.
6. The method for preparing a permanent antibacterial polyethersulfone membrane material as claimed in claim 2 or 5, characterized in that the solvent in the solution blending process in step (1) is N, N-dimethylformamide.
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Cited By (2)
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| CN112898715A (en) * | 2021-01-26 | 2021-06-04 | 嘉兴学院 | Persistent antibacterial polylactic acid composite material and preparation method thereof |
| WO2022194181A1 (en) * | 2021-03-17 | 2022-09-22 | 广州鹿山新材料股份有限公司 | Ionic antistatic polyethylene graft and preparation method therefor |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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