CN113896930A - N-halamine type acrylamide/polyvinyl alcohol-based antibacterial hydrogel and preparation method thereof - Google Patents
N-halamine type acrylamide/polyvinyl alcohol-based antibacterial hydrogel and preparation method thereof Download PDFInfo
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Abstract
The invention discloses an N-halamine type acrylamide/polyvinyl alcohol-based antibacterial hydrogel and a preparation method thereof. Cyanuric chloride is used as a main raw material, a halamine antibacterial agent precursor is prepared by a cyanuric chloride hydrolysis method, and is grafted onto poly (N-isopropylacrylamide)/polyvinyl alcohol semi-interpenetrating network hydrogel, and the N-halamine type acrylamide/polyvinyl alcohol based antibacterial hydrogel is obtained through chlorination. The initiator is utilized to initiate carbon-carbon double bonds on the N-isopropylacrylamide to carry out free radical polymerization, and the poly-N-isopropylacrylamide and the polyvinyl alcohol are crosslinked through the electrostatic complexation of amino groups of the poly-N-isopropylacrylamide and hydroxyl groups of the polyvinyl alcohol to form the semi-interpenetrating network hydrogel with certain mechanical properties. The components are cooperated with each other, so that the antibacterial property is strong.
Description
Technical Field
The invention relates to an N-halamine type acrylamide/polyvinyl alcohol-based antibacterial hydrogel and a preparation method thereof, belonging to the technical field of sewage treatment.
Background
Bacteria, molds and viruses continue to threaten human health, and particularly recently, large-scale transmission of viruses has a great influence on the life style and the economic level of people. Among various antibacterial materials, antibacterial hydrogel has been widely noticed in the inhibition of bacterial growth due to its various excellent properties such as water absorption, oxidation resistance, self-healing property, etc. The N-halamine type antibacterial material is relatively low in price, good in antibacterial performance and reusable. With the development of industrialization, water treatment is becoming a global research subject. Therefore, it is required to develop an antibacterial material having high bactericidal activity, broad-spectrum antibacterial property and water absorption property.
The hydrogel is a high-hydration polymer material with a three-dimensional network, and the excellent characteristics of the hydrogel are widely concerned in the antibacterial field. Generally prepared from natural or synthetic polymers, has the advantages of high water absorption, adjustable mechanical properties and the like. The natural polymer hydrogel material is prepared by adopting a physical crosslinking or chemical crosslinking mode, the mechanical property of the natural polymer hydrogel material is weaker, and an antibacterial agent is required to be added externally for synthesizing the polymer hydrogel.
The N-halamine type antibacterial agent usually contains one or more N-X bonds (X is Br, I and Cl), wherein the N-Cl bonds are common, and are oxidized by hypohalite, so that the N-H bonds are converted into the N-X bonds, and after the antibacterial effect is finished, the sodium hypohalite can be soaked again to achieve the effect of sterilizing again, and the recycling property is strong.
N-isopropylacrylamide and polyvinyl alcohol are two common and conveniently available substrates, and the addition of N-isopropylacrylamide makes the hydrogel both pH and temperature sensitive. Meanwhile, the semi-interpenetrating network hydrogel prepared by combining the poly-N-isopropylacrylamide and the polyvinyl alcohol has better mechanical property. After the hydrogel is combined with the antibacterial agent, the hydrogel can be better applied to water treatment, antibacterial coating materials and material surface antibacterial by utilizing the characteristic of the plasticity of the hydrogel.
Disclosure of Invention
The invention aims to provide an N-halamine type acrylamide/polyvinyl alcohol-based antibacterial hydrogel and a preparation method thereof, and aims to solve the problems in the prior art. The invention prepares poly N-isopropyl acrylamide/polyvinyl alcohol semi-interpenetrating network hydrogel through free radical polymerization, and grafts the halamine precursor prepared by cyanuric chloride by a hydrolysis method onto the poly N-isopropyl acrylamide/polyvinyl alcohol semi-interpenetrating network hydrogel, and obtains the required antibacterial hydrogel under the chlorination action. The synthesized hydrogel has the characteristics of simple synthesis process, mild reaction conditions, broad-spectrum antibiosis, adjustable mechanical properties and the like.
To achieve the above object. The invention adopts the following technical scheme:
a preparation method of N-halamine type acrylamide/polyvinyl alcohol-based antibacterial hydrogel comprises the following steps:
(1) preparing a certain amount of polyvinyl alcohol aqueous solution, adding a certain amount of N-isopropylacrylamide, an initiator, a cross-linking agent, deionized water and the prepared polyvinyl alcohol aqueous solution into a beaker, uniformly stirring, reacting in a constant-temperature water bath kettle, purifying the prepared hydrogel in the deionized water, and freeze-drying the swollen and purified hydrogel;
(2) weighing quantitative cyanuric chloride, sodium hydroxide and deionized water, adding the weighed cyanuric chloride, sodium hydroxide and deionized water into a beaker, uniformly stirring, placing the beaker under an ice bath condition, adding freeze-dried gel into the beaker, dropwise adding a NaOH solution, soaking and purifying hydrogel after complete reaction, and then freeze-drying;
(3) and (3) placing the hydrogel in NaClO solution for chlorination soaking at room temperature, and then purifying in deionized water to obtain the N-halamine type acrylamide/polyvinyl alcohol-based antibacterial hydrogel.
Preferably, in the step (1), the concentration of the polyvinyl alcohol aqueous solution is 3% by mass, and the quantitative N-isopropylacrylamide is 2g/100 ml.
Preferably, in the step (1), the initiator is ammonium persulfate, and the crosslinking agent is N, N' -methylene-bisacrylamide. The mass concentration of the initiator in the reaction system is 0.2%, and the mass concentration of the cross-linking agent is 0.02%.
Preferably, in the step (1), the mixed solution is sufficiently stirred under a nitrogen atmosphere and dispersed in an ultrasonic machine for 20min or more.
Preferably, in the step (1), the constant-temperature water bath is 50-60 ℃ and the reaction time is 3-4 h.
Preferably, in the step (1), the soaking purification is to wash and soak for 3 to 5 times by using deionized water, and the freeze-drying time is 1 to 2 days.
Preferably, in the step (2), the quantitative content of the cyanuric chloride is 1.39g/60ml, the quantitative content of the sodium hydroxide is 0.604g/60ml, and the quantitative content of the deionized water is 60 ml.
Preferably, in the step (2), the dropping process needs to be slowly dropped and continuously stirred, the dropping process is 1-2 hours, and the reaction time is 3-4 hours.
Preferably, in step (2), the temperature of the ice-water bath is kept between 0 and 5 ℃.
Preferably, in the step (2), the mass percentage of the dropwise added sodium hydroxide is 10%.
Preferably, in the step (2), the soaking purification is to wash and soak for 3 to 5 times by using deionized water, and the freeze-drying time is 1 to 2 days.
Preferably, in the step (3), the NaClO solution is chlorinated and soaked for 1-2h at room temperature under the condition that the mass concentration of the NaClO solution is 10% -30%.
Compared with the prior art, the invention has the beneficial effects that:
the invention utilizes a blending method, adopts free radical polymerization to prepare the poly-N-isopropylacrylamide/polyvinyl alcohol semi-interpenetrating network hydrogel under specific conditions, and has simple operation and higher condition controllability. And secondly, the mechanical property of the hydrogel is enhanced by utilizing the electrostatic complexation of the amino group of the poly-N-isopropyl acrylamide and the hydroxyl group of the polyvinyl alcohol. Compared with the method of adding crosslinking agents such as glutaraldehyde into PVA, the method of the invention is more environment-friendly and safer.
The composite material obtained by the invention is grafted to polyvinyl alcohol by utilizing the hydrolysis of cyanuric chloride, and has antibacterial performance after chlorination. Compared with the common acrylamide/polyvinyl alcohol-based antibacterial material, the N-halamine-type antibacterial material can be recycled and has low price. The hydrolysis condition of cyanuric chloride is easy to control, convenient to operate, and has wide prospects in the fields of water treatment, antibacterial coatings and the like.
Drawings
FIG. 1 is an antibacterial test chart: the N-halamine type acrylamide/polyvinyl alcohol-based antibacterial hydrogel obtained by the invention has an antibacterial experiment effect diagram for escherichia coli and staphylococcus aureus (the left column is a comparative example 1, and the right column is an example 3).
FIG. 2 is a reaction scheme: the reaction mechanism of the N-halamine type acrylamide/polyvinyl alcohol-based antibacterial hydrogel obtained by the invention is disclosed.
Detailed description of the invention
The invention will be better understood from the following examples. However, those skilled in the art will readily appreciate that the description of the embodiments is only illustrative of the present invention and should not be taken as limiting the invention as detailed in the claims.
Example 1
A preparation method of N-halamine type acrylamide/polyvinyl alcohol-based antibacterial hydrogel comprises the following steps:
(1) adding N-isopropylacrylamide, ammonium persulfate, N' -methylenebisacrylamide and 100ml of deionized water into a beaker, fully stirring stock solution in the beaker under the nitrogen atmosphere, dispersing in an ultrasonic machine for 20min, pouring into a glass mold after uniform dispersion, and placing the glass mold in a constant-temperature water bath kettle at 60 ℃ for reaction for 4h to obtain the composite hydrogel. Purifying the prepared hydrogel in deionized water, and freeze-drying the hydrogel after swelling and purification, wherein the mass concentration of ammonium persulfate in the stock solution is 0.2%, and the mass concentration of N, N' -methylene-bisacrylamide in the stock solution is 0.02%;
(2) weighing 1.39g of cyanuric chloride, 0.604g of sodium hydroxide and 60ml of deionized water, adding the cyanuric chloride, the 0.604g of sodium hydroxide and the 60ml of deionized water into a beaker, uniformly stirring and dispersing the cyanuric chloride and the sodium hydroxide in an ultrasonic machine for 20min, placing a glass mold in an ice bath condition at 0-5 ℃, stirring at a low speed, adding the prepared freeze-dried gel into the beaker, weighing 13.2g of sodium hydroxide to prepare a 10% aqueous solution, slowly dropwise adding the sodium hydroxide into the beaker, stirring slowly in the dropwise adding process along with slow stirring, dropwise adding for 2 hours until the dropwise adding is finished, continuously reacting for 4 hours, continuously keeping the reaction system under the ice bath condition, soaking and purifying the hydrogel after complete reaction, and then freeze-drying;
(3) and (3) soaking the hydrogel in a NaClO solution with the pH value of 7 and the mass fraction of 10% for 2h at room temperature, purifying and freeze-drying in deionized water. And obtaining the N-halamine type acrylamide/polyvinyl alcohol-based antibacterial hydrogel.
Example 2
A preparation method of N-halamine type acrylamide/polyvinyl alcohol-based antibacterial hydrogel comprises the following steps:
(1) weighing a certain amount of polyvinyl alcohol to prepare an aqueous solution with the mass fraction of 3%, adding N-isopropylacrylamide, ammonium persulfate, N' -methylenebisacrylamide, 5ml of deionized water and 5ml of the aqueous solution of the polyvinyl alcohol into a beaker, fully stirring the stock solution in the beaker in a nitrogen atmosphere, dispersing for 20min in an ultrasonic machine, pouring the dispersed stock solution into a glass mold after uniform dispersion, and placing the glass mold in a constant-temperature water bath kettle at 60 ℃ for reaction for 4h to obtain the composite hydrogel. Purifying the prepared hydrogel in deionized water, and freeze-drying the hydrogel after swelling and purification, wherein the mass concentration of ammonium persulfate in the stock solution is 0.2%, and the mass concentration of N, N' -methylene-bisacrylamide in the stock solution is 0.02%;
(2) weighing 1.39g of cyanuric chloride, 0.604g of sodium hydroxide and 60ml of deionized water, adding the cyanuric chloride, the 0.604g of sodium hydroxide and the 60ml of deionized water into a beaker, uniformly stirring and dispersing the cyanuric chloride and the sodium hydroxide in an ultrasonic machine for 20min, placing a glass mold in an ice bath condition at 0-5 ℃, stirring at a low speed, adding the prepared freeze-dried gel into the beaker, weighing 13.2g of sodium hydroxide to prepare a 10% aqueous solution, slowly dropwise adding the sodium hydroxide into the beaker, stirring slowly in the dropwise adding process along with slow stirring, dropwise adding for 2 hours until the dropwise adding is finished, continuously reacting for 4 hours, continuously keeping the reaction system under the ice bath condition, soaking and purifying the hydrogel after complete reaction, and then freeze-drying;
(3) and (3) placing the hydrogel in 10% NaClO solution with the pH value of 7 at room temperature for soaking for 2h, purifying and freeze-drying in deionized water to obtain the N-halamine type acrylamide/polyvinyl alcohol-based antibacterial hydrogel.
Example 3
A preparation method of N-halamine type acrylamide/polyvinyl alcohol-based antibacterial hydrogel comprises the following steps:
(1) weighing a certain amount of polyvinyl alcohol to prepare an aqueous solution with the mass fraction of 3%, adding N-isopropylacrylamide, ammonium persulfate, N' -methylenebisacrylamide and 10ml of the aqueous solution of the polyvinyl alcohol into a beaker, fully stirring the stock solution in the beaker in the nitrogen atmosphere, dispersing for 20min in an ultrasonic machine, pouring the uniformly dispersed stock solution into a glass mold, and placing the glass mold in a constant-temperature water bath kettle at 60 ℃ for reaction for 4h to obtain the composite hydrogel. Purifying the prepared hydrogel in deionized water, and freeze-drying the hydrogel after swelling and purification, wherein the mass concentration of ammonium persulfate in the stock solution is 0.2%, and the mass concentration of N, N' -methylene-bisacrylamide in the stock solution is 0.02%;
(2) weighing 1.39g of cyanuric chloride, 0.604g of sodium hydroxide and 60ml of deionized water, adding the cyanuric chloride, the 0.604g of sodium hydroxide and the 60ml of deionized water into a beaker, uniformly stirring and dispersing the cyanuric chloride and the sodium hydroxide in an ultrasonic machine for 20min, placing a glass mold in an ice bath condition at 0-5 ℃, stirring at a low speed, adding the prepared freeze-dried gel into the beaker, weighing 13.2g of sodium hydroxide to prepare a 10% aqueous solution, slowly dropwise adding the sodium hydroxide into the beaker, stirring slowly in the dropwise adding process along with slow stirring, dropwise adding for 2 hours until the dropwise adding is finished, continuously reacting for 4 hours, continuously keeping the reaction system under the ice bath condition, soaking and purifying the hydrogel after complete reaction, and then freeze-drying;
(3) and (3) placing the hydrogel into a NaClO solution with the pH value of 7 and the mass fraction of 10% at room temperature, soaking for 2h, purifying and freeze-drying in deionized water, and thus obtaining the N-halamine type acrylamide/polyvinyl alcohol-based antibacterial hydrogel.
The antibacterial properties of the materials obtained in example 3 and comparative example 1 (polyvinyl alcohol hydrogel without N-halamine type acrylamide) were measured, and the results are shown in Table 1.
Table 1 results of antibacterial properties of the materials obtained in example 3 and comparative example 1
| Material | Bacteriostatic effect |
| Example 3 | Sterile colony generation |
| Comparative example 1 | Colony formation |
The method is known that the poly-N-isopropylacrylamide/polyvinyl alcohol-based hydrogel generates certain antibacterial property after being grafted with the halamine precursor, and the antibacterial effect is still good after multiple times of swelling and freeze-drying. Therefore, the antibacterial hydrogel product prepared by the method has certain antibacterial performance.
In conclusion, the application provides a method for preparing semi-interpenetrating network hydrogel by using poly-N-isopropylacrylamide/polyvinyl alcohol through initiating a free radical polymerization reaction and an electrostatic complexation reaction by using an initiator, after the mechanical property is enhanced, a halamine antibacterial agent precursor is prepared by a cyanuric chloride hydrolysis method and grafted onto the poly-N-isopropylacrylamide/polyvinyl alcohol semi-interpenetrating network hydrogel, and the N-halamine type acrylamide/polyvinyl alcohol based antibacterial hydrogel is obtained through chlorination. The hydrogel not only has stronger broad-spectrum antibacterial performance, but also can be recycled. Is expected to be applied and developed in the fields of water treatment, antibacterial coating materials, material surface antibacterial and the like in the later period.
The applicant states that the present invention is illustrated by the above examples to the N-halamine type acrylamide/polyvinyl alcohol based antibacterial hydrogel and the preparation method thereof, but the present invention is not limited to the above examples, i.e., it does not mean that the present invention must be implemented by relying on the above examples. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (10)
1. A preparation method of N-halamine type acrylamide/polyvinyl alcohol-based antibacterial hydrogel is characterized by comprising the following steps: the method comprises the following steps:
(1) preparing a certain amount of polyvinyl alcohol aqueous solution, adding a certain amount of N-isopropylacrylamide, an initiator, a cross-linking agent, deionized water and the prepared polyvinyl alcohol aqueous solution into a beaker, uniformly stirring, reacting in a constant-temperature water bath kettle, purifying the prepared hydrogel in the deionized water, and freeze-drying the swollen and purified hydrogel;
(2) weighing quantitative cyanuric chloride, sodium hydroxide and deionized water, adding the weighed cyanuric chloride, sodium hydroxide and deionized water into a beaker, uniformly stirring, placing the beaker under an ice bath condition, adding freeze-dried gel into the beaker, dropwise adding a NaOH solution, soaking and purifying hydrogel after complete reaction, and then freeze-drying;
(3) and (3) soaking the hydrogel in a NaClO solution at room temperature, and purifying in deionized water to obtain the N-halamine type acrylamide/polyvinyl alcohol-based antibacterial hydrogel.
2. The method according to claim 1, wherein the polyvinyl alcohol aqueous solution of step (1) has a mass concentration of 3% and N-isopropylacrylamide is 2g/10 ml.
3. The preparation method according to claim 1, wherein the initiator in the step (1) is ammonium persulfate, the crosslinking agent is N, N' -methylenebisacrylamide, and the mass concentration of the initiator and the mass concentration of the crosslinking agent in the reaction system are respectively 0.2% and 0.02%.
4. The preparation method according to claim 1, wherein the reaction system of step (1) is sufficiently stirred under nitrogen atmosphere and dispersed in an ultrasonic machine for 20min under the reaction conditions of 50-60 ℃ and the reaction time of 3-4 h.
5. The method according to claim 1, wherein in the step (2), the quantitative amounts of cyanuric chloride are 1.39g/60ml, sodium hydroxide is 0.604g/60ml, and deionized water is 60 ml.
6. The preparation method according to claim 1, wherein in the step (2), stirring is continuously carried out during the dropping process, the dropping process is carried out for 2 hours, the mass percentage of the dropped sodium hydroxide is 10%, and the reaction process is maintained at 0-5 ℃. The reaction time was 4 h.
7. The method according to claim 1, wherein in the step (2), the soaking purification is soaking 3-5 times by using deionized water, and the freeze-drying time is 1-2 days.
8. The preparation method according to claim 1, wherein in the step (2), the mass concentration of the NaClO solution is 10% -30%, and the chlorination soaking time is 1-2 h.
9. An N-halamine type acrylamide/polyvinyl alcohol based antibacterial hydrogel obtained by the method of any one of claims 1 to 8.
10. The use of the N-halamine-type acrylamide/polyvinyl alcohol-based antibacterial hydrogel according to claim 9 in the fields of water treatment, antibacterial coating materials and antibacterial material surface.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115368638A (en) * | 2022-08-10 | 2022-11-22 | 河南师范大学 | Preparation method and application of multifunctional modified starch-based hydrogel material |
| CN115651374A (en) * | 2022-10-24 | 2023-01-31 | 福建亮点印务有限公司 | Environment-friendly antibacterial food-grade packaging bag and preparation method thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115368638A (en) * | 2022-08-10 | 2022-11-22 | 河南师范大学 | Preparation method and application of multifunctional modified starch-based hydrogel material |
| CN115651374A (en) * | 2022-10-24 | 2023-01-31 | 福建亮点印务有限公司 | Environment-friendly antibacterial food-grade packaging bag and preparation method thereof |
| CN115651374B (en) * | 2022-10-24 | 2023-10-24 | 福建亮点印务有限公司 | Environment-friendly antibacterial food-grade packaging bag and preparation method thereof |
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| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20220107 |