CN113058444A - A kind of polyionic liquid/EVA composite antibacterial film and its preparation and application method - Google Patents
A kind of polyionic liquid/EVA composite antibacterial film and its preparation and application method Download PDFInfo
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- CN113058444A CN113058444A CN202110445812.7A CN202110445812A CN113058444A CN 113058444 A CN113058444 A CN 113058444A CN 202110445812 A CN202110445812 A CN 202110445812A CN 113058444 A CN113058444 A CN 113058444A
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- 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
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- 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
- B01D67/0009—Organic membrane manufacture by phase separation, sol-gel transition, evaporation or solvent quenching
- B01D67/0011—Casting solutions therefor
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- 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
- B01D69/12—Composite membranes; Ultra-thin membranes
- B01D69/125—In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2325/00—Details relating to properties of membranes
- B01D2325/48—Antimicrobial properties
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Abstract
The invention relates to a polyion liquid/EVA composite antibacterial film and preparation and application thereof, belonging to the technical field of antibacterial materials. The polyion liquid/EVA composite antibacterial membrane is prepared by polymerizing imidazole organic matters and halogenated normal alkyl serving as raw materials to prepare alkyl imidazolium salt ionic liquid, polymerizing to synthesize an anion framework, grafting and introducing imidazolium salt to prepare imidazole ionic liquid, and mixing the imidazole ionic liquid with EVA to prepare the composite antibacterial membrane. The imidazole polyionic liquid is applied to preparation of the composite antibacterial film, and the product is excellent in antibacterial performance. Because the EVA is mixed and dissolved, the optical fiber has excellent optical performance, weather resistance, corrosion resistance, non-toxic and pollution-free characteristics, high stretchability and good processability. And the discarded antibacterial film is convenient to recover, and the economical efficiency of the process is greatly improved. The preparation method is simple and easy to implement, is convenient for industrial popularization and application, and can be applied to the fields of clinical medical instruments and antibacterial materials.
Description
Technical Field
The invention belongs to the technical field of antibacterial materials, and particularly relates to a polyion liquid/EVA composite antibacterial film and preparation and application methods thereof.
Background
In recent years, with the emergence of bacterial resistance due to the use of a large amount of antibiotics, the effects of traditional antibacterial drugs are greatly reduced, and therefore, research and manufacture of novel antibacterial drugs or materials become problems to be solved at present. Tracheotomy is an effective way to improve the ventilation state of a patient, but belongs to invasive operation, increases the risk of lung infection of the patient and increases the treatment burden of the patient. The previous research shows that the change of respiratory flora after tracheotomy can increase the risk of lung infection, so the novel composite antibacterial material has positive effect on ensuring the safety of patients.
Ionic liquids have been widely reported as an antibacterial material, and the antibacterial mechanism thereof is mainly that cations are combined with electronegative cell membranes of bacteria through electrostatic interaction, and meanwhile, hydrophobic alkyl chains are inserted into phospholipid bilayers to cause cell membrane rupture and finally cause bacterial death.
Polyionic liquids are a class of materials that incorporate ionic liquid units into the polymer structure to achieve both ionic liquid and polymer properties. The polyion liquid has a designable structure, controllable adjustment of polymer molecular weight, glass transition temperature, hydrophilic-hydrophobic water balance, charge density and counter ions can be realized by changing the species of ionic liquid groups, polyion liquids with different physical and chemical properties are obtained, and the polyion liquid has a wide application prospect in the antibacterial field. However, systematic research on the influence of the structure of polyionic liquid, including the type of cation, the configuration of antibacterial group and the type of chemical bond on the antibacterial activity of polymer is the focus and difficulty of research and discussion at home and abroad.
For the polyion liquid, the antibacterial performance is in certain connection with a substituent group at the N3 position, when the substituent group at the N3 position is an alkyl chain, the antibacterial performance of the imidazolium salt can be influenced by the length of the alkyl chain, and within a certain range, the longer the alkyl chain is, the stronger the antibacterial performance is. The imidazole polyionic liquid substituted by long carbon chains is gathered in suspension, and hydrophobic end groups (carbon chains) tend to be inserted into hydrophobic cell walls, so that the antibacterial activity is increased; and the charge density of the imidazolium salt is increased, so that the antibacterial performance of the imidazole-based ionic liquid is stronger.
The ethylene-vinyl acetate copolymer (EVA) is obtained by copolymerizing a nonpolar ethylene monomer and a strong polar vinyl acetate monomer, and due to the introduction of the vinyl acetate monomer, the compatibility, the transparency, the flexibility, the impact resistance and other properties of polyethylene are improved. The EVA copolymer has excellent optical performance, low temperature resistance (-58 ℃), environmental stress cracking resistance, chemical corrosion resistance, non-toxicity, no pollution, high stretchability, good processability and the like. Therefore, the EVA copolymer is widely applied to the material fields of packaging films, agricultural films, hot melt adhesives, coatings, printing inks, wires and cables, pour point depressants and the like. The difference of VA content can cause the property of EVA copolymer material to have great difference, so that the EVA copolymer material can be applied in a plurality of different fields, and the EVA is concerned as a novel film-making material.
The Chinese invention patent CN110643107A discloses a mildew-proof antibacterial transparent PEVA film and a preparation process thereof, wherein the film improves the transparency, softness and toughness of the PEVA film and increases the application range of the PEVA film by increasing the content of vinyl acetate of the PEVA film, but the implementation conditions of the patent are too harsh, the temperature is too high, and the antibacterial property needs to be improved; chinese patent CN110917381A discloses a bacterial cellulose/polyion liquid antibacterial film and a preparation method thereof, the composite film has low toxicity and good degradability, but the antibacterial performance of the composite film is relatively weak. Therefore, there is an urgent need to develop a novel green antibacterial material which is easily degradable and has good antibacterial properties.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides a polyion liquid/EVA composite membrane and a preparation and application method thereof. The prepared polyion liquid/EVA composite membrane not only has the characteristics of excellent optical performance, weather resistance, corrosion resistance, no toxicity and no pollution, but also has high stretchability, good processability and excellent antibacterial performance, and can be widely applied to the fields of clinical medical instruments and antibacterial materials as the antibacterial material.
In order to realize the purpose of the invention, the invention is realized by adopting the following technical route:
the polyion liquid/EVA composite antibacterial membrane is a composite membrane prepared by mixing and dissolving an imidazole polyion liquid prepared by grafting alkyl imidazole salt onto an anionic polymer serving as a framework and EVA, wherein the mass ratio of the imidazole polyion liquid to the EVA is 0.1-10: 1.
Preferably, the content of vinyl acetate in the EVA is 1% -70%.
The preparation method of the polyion liquid/EVA composite antibacterial film comprises the following steps:
s1: mixing imidazole organic matters and halogenated normal alkyl uniformly, and reacting and refluxing; cooling after the reaction is finished to obtain alkyl imidazolium salt ionic liquid;
s2: dissolving the alkyl imidazolium salt ionic liquid prepared in the step S1, an anionic polymer monomer serving as a framework, an initiator and a cross-linking agent in a solvent, uniformly mixing by ultrasonic waves, polymerizing, washing and drying to obtain an imidazole ionic liquid;
s3: and (4) dissolving the polyion liquid prepared in the step (S2) in an organic solvent, uniformly mixing with an EVA organic solution to obtain a composite membrane material, and pouring to form a membrane to obtain the polyion liquid/EVA composite antibacterial membrane.
Preferably, the molar ratio of the imidazole-based organic compound to the halogenated n-alkyl in step S1 is 1-10: 1.
Preferably, the carbon chain length of the halogenated n-alkyl group in the step S1 is 1 to 12.
Preferably, in the step S1, the reaction time of the imidazole-based organic compound and the halogenated n-alkyl group is 1 to 24 hours, the reflux time is 24 to 96 hours, and the reaction temperature is 20 to 200 ℃.
Preferably, the anionic polymer monomer as a backbone described in step S2 is any one or two of amino acid, vinylbenzene, 2-acrylamido-2-methylpropanesulfonic acid, vinylamino acid, divinylbenzene and isopropylnitrile.
Preferably, the molar ratio of the alkyl imidazolium salt ionic liquid to the anionic polymer monomer as the framework in the step S2 is 0.1-10: 1.
Preferably, the amount of the initiator used in step S2 is 0.1% to 20% of the total mass of the polymerized monomers.
Preferably, the amount of the cross-linking agent used in step S2 is 0.1% to 50% of the total mass of the polymerized monomers.
Preferably, the drying in step S2 is vacuum drying, and the vacuum drying time is 5-30 h.
Preferably, in the step S3, the film forming time is 1-24 hours, and the film forming temperature is 10-100 ℃.
The polyion liquid/EVA composite antibacterial film is applied to clinical medical instruments and daily necessities antibacterial material products.
The invention has the advantages of
(1) The polyion liquid/EVA composite antibacterial membrane is prepared by polymerizing imidazole organic matters and halogenated normal alkyl serving as raw materials to prepare alkyl imidazole salt ionic liquid, grafting the alkyl imidazole salt ionic liquid by taking an anionic polymer as a framework to prepare the imidazole polyion liquid with antibacterial property, and applying the imidazole polyion liquid to the preparation of the composite antibacterial membrane, so that the product is excellent in antibacterial property.
(2) The polyion liquid/EVA composite antibacterial film disclosed by the invention is miscible with EVA, so that the polyion liquid/EVA composite antibacterial film not only has excellent optical performance, weather resistance and corrosion resistance, but also has the characteristics of no toxicity and no pollution, and also has high stretchability and good processability.
(3) The preparation method of the polyion liquid/EVA composite antibacterial film modified by the imidazole ionic liquid is simple and easy, is convenient for industrial popularization and application, and provides a new choice for clinical medical instruments and antibacterial materials.
(4) The discarded antibacterial film of the polyion liquid/EVA composite antibacterial film modified by the imidazole ionic liquid is convenient to recover, and the process economy is greatly improved.
Detailed Description
The present invention is further illustrated by, but not limited to, the following examples.
Example 1:
the polyion liquid/EVA composite membrane described in this example 1 uses 2-acrylamide-2-methylpropanesulfonic acid as a framework, and alkyl imidazole is grafted, where the mass ratio of polyion liquid to EVA is 9: 1.
2.0g of imidazole and 4.1g of 1-bromobutane were dissolved in 25mL of acetonitrile; after being mixed evenly, 3.3g of potassium hydroxide is added for reflux reaction for 4 hours; cooling to room temperature after the reaction is finished, removing the solvent by rotary evaporation, purifying the crude product by column chromatography, and finally obtaining yellow oily liquid, wherein the mobile phase is ethyl acetate/methanol. Dissolving 2-acrylamide-2-methylpropanesulfonic Acid (ASP) and Azobisisobutyronitrile (AIBN) 0.155g in a proper amount of dimethyl sulfoxide, ultrasonically mixing, uniformly hooking, sealing in a 60 ℃ gas environment, polymerizing for 6 hours, washing with acetone after the reaction is finished, and drying to obtain the poly-2-acrylamide-2-methylpropanesulfonic acid. Dissolving the prepared poly (2-acrylamide-2-methylpropanesulfonic acid) and equimolar 1-butylimidazole in a proper amount of methanol, uniformly mixing, stirring at normal temperature for 24 hours, washing with diethyl ether for three times, and drying in a vacuum oven for 12 hours to obtain a product imidazole polyion liquid; dissolving EVA with 9gVA content of 10% in acetone under heating and stirring, adding 1g polyion liquid, stirring, mixing, pouring into film-forming mold, molding, and vacuum drying in a vacuum oven at 60 deg.CoAnd drying to form a film under the condition of C, thus obtaining the polyion liquid/EVA composite antibacterial film.
Example 2:
the mass ratio of the polyion liquid to the EVA is 9: 1.
The procedure for preparing the polyion liquid/EVA composite antibacterial film was the same as in example 1 except that 1-bromobutane in example 1 was changed to 1-bromoheptane.
Example 3:
the mass ratio of the polyion liquid to the EVA is 9: 2.
The other steps for preparing the polyion liquid/EVA composite antibacterial film are the same as the steps in the example 1.
Example 4:
the mass ratio of the polyion liquid to the EVA is 9: 1.
The EV content in the example 1 is changed from 10% to 25%, and the rest steps for preparing the polyion liquid/EVA composite antibacterial film are the same as the example 1.
Example 5:
1.8g of 1-vinylimidazole and 2.74g of n-butyl bromide were reacted at 25 ℃ with stirring for 72 h. After the reaction is finished, the mixture is respectively washed for 1 time by using ethyl acetate and anhydrous ether, and finally the mixture is put into a vacuum drying oven to be dried for 24 hours at the temperature of 30 ℃.
2g of prepared brominated 1-vinyl-3-butylimidazole, 1.5g of styrene, 6.5g of acrylonitrile, 0.1g of azobisisobutyronitrile and 0.12g of divinylbenzene were mixed and shaken with ultrasound to give a homogeneous solution; the mixed solution was then spread evenly on a glass plate and polymerized for 6 hours. Soaking and washing the polymerized polyion liquid with ethanol, and drying for 6 h. And then heating and stirring 9g of 10% EVA, dissolving in acetone, adding 1g of polyion liquid, stirring and mixing, pouring into a film forming mold for molding, and placing in a vacuum drying oven to dry at 60 ℃ for film forming to obtain the polyion liquid/EVA composite antibacterial film.
Example 6:
the mass ratio of the polyion liquid to the EVA is 9: 2.
The other steps for preparing the polyion liquid/EVA composite antibacterial film are the same as the steps in the example 5.
Example 7:
the mass ratio of the polyion liquid to the EVA is 9: 1.
The procedure for preparing a polyion liquid/EVA composite antibacterial film was the same as in example 5 except that 1-bromobutane in example 1 was changed to 1-bromoheptane.
Example 8:
the mass ratio of the polyion liquid to the EVA is 9: 1.
The EV content in the example 1 is changed from 10% to 25%, and the rest steps for preparing the polyion liquid/EVA composite antibacterial film are the same as the steps in the example 5.
And (3) performance testing:
the polyion liquid/EVA composite antibacterial film prepared in the above examples 1 to 8 was subjected to antibacterial performance and mechanical performance tests:
and (3) antibacterial property test: mixing the bacterial liquid with PET film and polyion liquid film (area of 1.5 × 1.5 cm)2) Co-cultivation at 37 ℃ for 4h, after which aspirationWherein 10 mu L of bacterial liquid is transferred to an LB solid agar plate, the bacterial liquid is evenly spread, the bacterial liquid is put into a constant temperature incubator at 37 ℃ for 24 hours, and the number of macroscopic colonies is counted. Triplicate experiments were repeated for each well plate test. The antibacterial rate was calculated according to the following formula (A and B represent the number of colonies in the control group and the experimental group, respectively):
the test results were as follows:
table-antibacterial property comparison data table
Table two mechanical property comparison data table
The detection result shows that: the cation in the imidazole ionic liquid in the polyion liquid/EVA composite antibacterial film has a broad-spectrum antibacterial effect, so that the prepared composite antibacterial film has excellent antibacterial performance. Meanwhile, the EVA is mixed and dissolved, so that the paint has the characteristics of excellent optical performance, weather resistance, corrosion resistance, no toxicity, no pollution, high stretchability and good processability.
The foregoing is illustrative and explanatory only and is not intended to be exhaustive or to limit the invention to the precise embodiments described, and various modifications, additions, and substitutions may be made by those skilled in the art without departing from the scope of the invention or exceeding the scope of the claims.
Claims (10)
1. The polyion liquid/EVA composite antibacterial membrane is a composite membrane prepared by mixing and dissolving an imidazole polyion liquid prepared by grafting alkyl imidazole salt onto an anionic polymer serving as a framework and EVA, wherein the mass ratio of the imidazole polyion liquid to the EVA is 0.1-10: 1.
2. The polyion liquid/EVA composite antibacterial film according to claim 1, wherein: the content of vinyl acetate in the EVA is 1% -70%.
3. A method for preparing the polyion liquid/EVA composite antibacterial film according to claim 1, characterized by comprising the steps of:
s1: mixing imidazole organic matters and halogenated normal alkyl uniformly, and reacting and refluxing; cooling after the reaction is finished to obtain alkyl imidazolium salt ionic liquid;
s2: dissolving the alkyl imidazolium salt ionic liquid prepared in the step S1, an anionic polymer monomer serving as a framework, an initiator and a cross-linking agent in a solvent, uniformly mixing by ultrasonic waves, polymerizing, washing and drying to obtain an imidazole ionic liquid;
s3: and (4) dissolving the imidazole polyion liquid prepared in the step (S2) in an organic solvent, uniformly mixing with an EVA organic solution to obtain a composite membrane material, and pouring to form a membrane to obtain the polyion liquid/EVA composite antibacterial membrane.
4. The preparation method of the polyion liquid/EVA composite antibacterial film as claimed in claim 3, wherein the preparation method comprises the following steps: the molar ratio of the imidazole organic compound to the halogenated n-alkyl in the step S1 is 1-10: 1.
5. The preparation method of the polyion liquid/EVA composite antibacterial film as claimed in claim 3, wherein the preparation method comprises the following steps: the carbon chain length of the halogenated n-alkyl in the step S1 is 1-12.
6. The preparation method of the polyion liquid/EVA composite antibacterial film as claimed in claim 3, wherein the preparation method comprises the following steps: the reaction time of the imidazole organic compound and the halogenated normal alkyl in the step S1 is 1-24 hours, the reflux time is 24-96 hours, and the reaction temperature is 20-200 ℃.
7. The preparation method of the polyion liquid/EVA composite antibacterial film as claimed in claim 3, wherein the preparation method comprises the following steps: the anionic polymer monomer as a skeleton described in step S2 is any one or two of amino acid, vinylbenzene, 2-acrylamido-2-methylpropanesulfonic acid, vinylamino acid, divinylbenzene and isopropylnitrile.
8. The preparation method of the polyion liquid/EVA composite antibacterial film as claimed in claim 3, wherein the preparation method comprises the following steps: the molar ratio of the alkyl imidazolium salt ionic liquid to the anionic polymer monomer used as the framework in the step S2 is 0.1-10: 1.
9. The preparation method of the polyion liquid/EVA composite antibacterial film as claimed in claim 3, wherein the preparation method comprises the following steps: the using amount of the initiator in the step S2 is 0.1-20% of the total mass of the polymerized monomers; the dosage of the cross-linking agent is 0.1-50% of the total mass of the polymerized monomers; the drying is vacuum drying, and the vacuum drying time is 5-30 h; in the step S3, the film forming time is 1-24 hours, and the film forming temperature is 10-100 ℃.
10. The use of the polyion liquid/EVA composite antibacterial film according to any one of claims 1 to 9 in clinical medical instruments and antibacterial materials.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN118718762A (en) * | 2024-07-05 | 2024-10-01 | 杭州师范大学 | Amino ionic liquid grafted polyamide thin layer composite nanofiltration membrane and preparation method thereof |
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