CN115028904A - Biomass antibacterial composite membrane material and preparation method thereof - Google Patents
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Abstract
The invention relates to the technical field of biomass membrane materials, and discloses a biomass antibacterial composite membrane material and a preparation method thereof, carboxyl-terminated polyethylene glycol is subjected to acyl chlorination and then sequentially subjected to esterification and quaternization with 2-hydroxychlorobenzaldehyde and dimethyl tertiary amine to obtain quaternary ammonium salt-terminated benzaldehyde polyethylene glycol, thereby introducing quaternary ammonium salt benzaldehyde groups at the two ends of the polyethylene glycol, performing Schiff base reaction on the aldehyde groups at the two ends of the polyethylene glycol and the amino groups of the chitosan and the ammoniated cellulose microcrystals respectively, thereby the chitosan and the cellulose microcrystal are crosslinked through the polyethylene glycol to obtain the composite membrane material, the cellulose microcrystal is taken as a reinforcing phase, and the chitosan composite membrane crosslinked through the hydrophilic flexible polyethylene glycol molecular chain has excellent mechanical strength and hydrophilicity, and the composite membrane contains abundant alkyl quaternary ammonium salt, so that the membrane material has long-acting antibacterial performance.
Description
Technical Field
The invention relates to the technical field of biomass membrane materials, in particular to a biomass antibacterial composite membrane material.
Background
With the rapid development of modern industry, the challenges of energy crisis, environmental pollution, ecological damage and other problems are increasingly severe, so that the development of environment-friendly materials capable of replacing petroleum-based polymer materials is urgently needed, and the development and utilization of renewable resources in the nature are focused on the current research hotspots, such as cellulose, chitosan, sodium alginate and the like, which have the advantages of wide sources, environmental protection and no pollution, and are widely applied in various fields of daily life and industrial development.
Chitosan and its quaternary ammonium salt derivative have good bacteriostatic action, such advantages as the good film forming property, apply to aspects such as packaging material, medical health extensively, etc., preparation of the bacterial fiber of chitosan grafting and its application in the sanitary article, graft chitosan into bacterial cellulose chemically through Schiff's base reaction, the sanitary article assembled has good water absorption, preventing the back seepage and bacteriostatic property; the invention relates to a preparation of a cellulose/chitosan blended transparent film and research on barrier antibacterial property, which is to blend cellulose and chitosan to prepare a film to obtain a composite film material with excellent barrier property and antibacterial property.
Disclosure of Invention
Technical problem to be solved
Aiming at the defects of the prior art, the invention provides a biomass antibacterial composite membrane material.
(II) technical scheme
In order to realize the purpose, the invention provides the following technical scheme: a biomass antibacterial composite membrane comprises ethylene diamine cellulose and chitosan, and the preparation method of the composite membrane material comprises the following steps: dissolving chitosan into an acetic acid solution, adding an N, N-dimethylformamide solution of ethylenediamine cellulose, adding terminal quaternary ammonium salt benzaldehyde polyethylene glycol, reacting at 25-45 ℃ for 4-10 h, pouring the solution onto a glass plate after reaction, casting to form a film, drying to remove the solvent, adding the film into deionized water, soaking and washing to obtain the biomass antibacterial composite film material.
Preferably, the mass ratio of the chitosan, the ethylenediamine cellulose and the terminal quaternary ammonium salt benzaldehyde polyethylene glycol is controlled to be 100:12-30: 5-20.
Preferably, the preparation method of the ethylenediamine modified cellulose comprises the following steps: adding cellulose microcrystal into a sodium hydroxide solution, then adding an ethanol solution of epoxy chloropropane, reacting, adding a product of epoxidized cellulose sodium bicarbonate into a water solution of epoxidized cellulose sodium bicarbonate, and adding ethylenediamine, and reacting to obtain the ethylenediamine cellulose.
Preferably, the preparation method of the terminal quaternary ammonium salt benzaldehyde polyethylene glycol comprises the following steps:
(1) dissolving polyethylene glycol and succinic anhydride into chloroform, then dropwise adding pyridine, and reacting to obtain carboxyl-terminated polyethylene glycol; then dissolving the mixture into N, N-dimethylformamide, dropwise adding thionyl chloride in the nitrogen atmosphere, heating to 40-60 ℃, reacting for 5-12 h, concentrating under reduced pressure to remove the thionyl chloride, and washing a product with diethyl ether to obtain the end acyl chloride polyethylene glycol.
(2) Dissolving end acyl chloride polyethylene glycol into a reaction solvent, adding 2-hydroxychlorobenzaldehyde and triethylamine in an ice water bath, reacting for 1-2 h, stirring at room temperature for reacting for 12-24 h, concentrating under reduced pressure after reaction, adding trichloromethane and saturated sodium bicarbonate solution for extraction, drying an organic phase, and washing with diethyl ether to obtain the end chloromethyl benzaldehyde polyethylene glycol.
(3) Dissolving chloromethyl benzaldehyde polyethylene glycol into N, N-dimethylformamide, and adding dimethyl tertiary amine (CH) 3 (CH 2 ) n N(CH 3 ) 2 N = 9-17), heating to 80-110 ℃, reacting for 24-48 h, adding ethyl acetate and saturated sodium bicarbonate solution for extraction after the reaction, drying the organic phase, and washing with diethyl ether to obtain the quaternary ammonium salt-terminated benzaldehyde polyethylene glycol.
Preferably, the mass ratio of the terminal acyl chloride polyethylene glycol, the 2-hydroxychlorobenzaldehyde and the triethylamine in the step (2) is controlled to be 100:25-38: 12-20.
Preferably, the solvent in (2) comprises dichloromethane, trichloromethane, 1, 4-dioxane, tetrahydrofuran and N, N-dimethylformamide.
Preferably, the mass ratio of the chloromethylbenzaldehyde polyethylene glycol and the dimethyl tertiary amine in the step (3) is controlled to be 100: 0.8-3.
(III) advantageous technical effects
Compared with the prior art, the invention has the following beneficial technical effects:
in the biomass antibacterial composite membrane material, carboxyl-terminated polyethylene glycol is subjected to acyl chlorination and then sequentially subjected to esterification and quaternization with 2-hydroxychlorobenzaldehyde and dimethyl tertiary amine to obtain quaternary ammonium salt-terminated benzaldehyde polyethylene glycol, thereby introducing quaternary ammonium salt benzaldehyde groups at the two ends of the polyethylene glycol, performing Schiff base reaction on the aldehyde groups at the two ends of the polyethylene glycol and the amino groups of the chitosan and the ammoniated cellulose microcrystals respectively, thereby the chitosan and the cellulose microcrystal are crosslinked through the polyethylene glycol to obtain the composite membrane material, the cellulose microcrystal is taken as a reinforcing phase, and the chitosan composite membrane crosslinked through the hydrophilic flexible polyethylene glycol molecular chain has excellent mechanical strength and hydrophilicity, and the composite membrane contains abundant alkyl quaternary ammonium salt, so that the membrane material has long-acting antibacterial performance, and the composite membrane material has wide application prospects in the aspects of packaging, medical treatment and health care and the like.
Drawings
FIG. 1 is a FT-IR spectrum of the biomass antibacterial composite membrane of example 1.
FIG. 2 is a table of composite performance tests.
Detailed Description
Example 1
(1) Dissolving 1 g of polyethylene glycol 1000 and 0.6 g of succinic anhydride in chloroform, then dropwise adding 0.15 g of pyridine, heating to 60 ℃, carrying out reflux reaction for 4 hours, adding chloroform and saturated sodium bicarbonate solution for extraction after the reaction, drying an organic phase, washing with diethyl ether to obtain carboxyl-terminated polyethylene glycol, then dissolving the carboxyl-terminated polyethylene glycol in N, N-dimethylformamide, dropwise adding 2 mL of thionyl chloride in a nitrogen atmosphere, heating to 40 ℃, reacting for 12 hours, carrying out reduced pressure concentration to remove the thionyl chloride, and washing a product with diethyl ether to obtain the end acyl chloride polyethylene glycol.
(2) Dissolving 2 g of end acyl chloride polyethylene glycol into tetrahydrofuran, adding 0.62 g of 2-hydroxychlorobenzaldehyde and 0.32 g of triethylamine in an ice-water bath, reacting for 1 h, stirring at room temperature for 24 h, concentrating under reduced pressure after reaction, adding trichloromethane and a saturated sodium bicarbonate solution for extraction, drying an organic phase, and washing with diethyl ether to obtain the end chloromethyl benzaldehyde polyethylene glycol.
(3) Dissolving 2 g of chloromethylbenzaldehyde polyethylene glycol into N, N-dimethylformamide, adding 0.016 g of ethyl acetate solution of dodecyl dimethyl tertiary amine, heating to 110 ℃ for reaction for 36 h, adding ethyl acetate and saturated sodium bicarbonate solution for extraction after reaction, drying an organic phase, and washing with diethyl ether to obtain quaternary ammonium salt-terminated benzaldehyde polyethylene glycol;
(4) adding 0.5 g of cellulose microcrystal into a 5% sodium hydroxide solution, then adding an ethanol solution containing 2.8 g of epichlorohydrin, heating to 65 ℃, reacting for 5 hours, adding distilled water to dilute and precipitate after the reaction, filtering a solvent, washing by distilled water, then weighing 0.5 g of product epoxidized cellulose, adding the weighed product epoxidized cellulose into a 1% sodium bicarbonate aqueous solution, adding 2.2 g of ethylenediamine, heating to 90 ℃, reacting for 8 hours, adding distilled water to dilute and precipitate after the reaction, filtering, and washing by deionized water to obtain ethylenediamine cellulose;
(5) dissolving 5 g of chitosan into 1% to obtain an acetic acid solution, then adding 0.6 g of N, N-dimethylformamide solution of ethylene diamine cellulose, adding 0.25 g of terminal quaternary ammonium salt benzaldehyde polyethylene glycol, reacting for 4 hours at 40 ℃, pouring the solution on a glass plate for casting to form a film after reaction, drying to remove the solvent, and adding the film into deionized water for dipping and washing to obtain the biomass antibacterial composite film material.
Example 2
(2) Dissolving 2 g of terminal acyl chloride polyethylene glycol into dichloromethane, adding 0.76 g of 2-hydroxychlorobenzaldehyde and 0.4 g of triethylamine in an ice-water bath, reacting for 2 h, stirring at room temperature for reacting for 18 h, concentrating under reduced pressure after reaction, adding trichloromethane and a saturated sodium bicarbonate solution for extraction, drying an organic phase, and washing with diethyl ether to obtain the terminal chlorotoluyl benzaldehyde polyethylene glycol.
(3) Dissolving 2 g of chloromethylbenzaldehyde polyethylene glycol into N, N-dimethylformamide, adding 0.045 g of ethyl acetate solution of tetradecyl dimethyl tertiary amine, heating to 110 ℃, reacting for 24 h, adding ethyl acetate and saturated sodium bicarbonate solution after reaction, extracting, drying an organic phase, and washing with diethyl ether to obtain the quaternary ammonium salt-terminated benzaldehyde polyethylene glycol.
(3) Dissolving 5 g of chitosan into 2% to obtain an acetic acid solution, then adding 0.8 g of N, N-dimethylformamide solution of ethylene diamine cellulose, adding 0.5 g of terminal quaternary ammonium salt benzaldehyde polyethylene glycol, reacting for 10 hours at 25 ℃, pouring the solution on a glass plate for casting to form a film after reaction, drying to remove the solvent, and adding the film into deionized water for dipping and washing to obtain the biomass antibacterial composite film material.
Example 3
(2) Dissolving 2 g of end acyl chloride polyethylene glycol into 1, 4-dioxane, adding 0.5 g of 2-hydroxychlorobenzaldehyde and 0.28 g of triethylamine in an ice-water bath, reacting for 1 h, stirring at room temperature for reacting for 24 h, concentrating under reduced pressure after reaction, adding trichloromethane and a saturated sodium bicarbonate solution for extraction, drying an organic phase, and washing with diethyl ether to obtain the end chloromethyl benzaldehyde polyethylene glycol.
(3) Dissolving 2 g of chloromethylbenzaldehyde polyethylene glycol into N, N-dimethylformamide, then adding 0.016 g of ethyl acetate solution of N, N-dimethyldecylamine, heating to 80 ℃ for reaction for 48 h, adding ethyl acetate and saturated sodium bicarbonate solution for extraction after the reaction, drying an organic phase, and washing with diethyl ether to obtain the terminal quaternary ammonium salt benzaldehyde polyethylene glycol.
(3) Dissolving 5 g of chitosan into 1% to obtain an acetic acid solution, then adding 1.2 g of N, N-dimethylformamide solution of ethylene diamine cellulose, adding 0.8 g of terminal quaternary ammonium salt benzaldehyde polyethylene glycol, reacting for 4 hours at 45 ℃, pouring the solution on a glass plate for casting to form a film after reaction, drying to remove the solvent, and adding the film into deionized water for dipping and washing to obtain the biomass antibacterial composite film material.
Example 4
(2) Dissolving 2 g of terminal acyl chloride polyethylene glycol into trichloromethane, adding 0.5 g of 2-hydroxychlorobenzaldehyde and 0.24 g of triethylamine in an ice-water bath, reacting for 2 h, stirring at room temperature for reacting for 18 h, concentrating under reduced pressure after reaction, adding trichloromethane and a saturated sodium bicarbonate solution for extraction, drying an organic phase, and washing with diethyl ether to obtain the terminal chlorotoluyl benzaldehyde polyethylene glycol.
(3) Dissolving 2 g of chloromethylbenzaldehyde polyethylene glycol into N, N-dimethylformamide, adding 0.06 g of ethyl acetate solution of hexadecyl dimethyl tertiary amine, heating to 110 ℃ for reaction for 24 hours, adding ethyl acetate and saturated sodium bicarbonate solution for extraction after the reaction, drying an organic phase, and washing with diethyl ether to obtain the quaternary ammonium salt-terminated benzaldehyde polyethylene glycol.
(3) Dissolving 5 g of chitosan into 2% to obtain an acetic acid solution, then adding 1.5 g of N, N-dimethylformamide solution of ethylene diamine cellulose, adding 1 g of terminal quaternary ammonium salt benzaldehyde polyethylene glycol, reacting for 10 hours at 25 ℃, pouring the solution on a glass plate to form a film by tape casting after the reaction, drying to remove the solvent, and adding the film into deionized water to dip and wash to obtain the biomass antibacterial composite film material.
Comparative example 1
(2) Dissolving 2 g of terminal acyl chloride polyethylene glycol into N, N-dimethylformamide, adding 0.62 g of 2-hydroxychlorobenzaldehyde and 0.28 g of triethylamine in an ice-water bath, reacting for 2 hours, then stirring at room temperature for reacting for 18 hours, concentrating under reduced pressure after reaction, adding trichloromethane and a saturated sodium bicarbonate solution for extraction, drying an organic phase, and washing with diethyl ether to obtain the terminal chlorobenzaldehyde polyethylene glycol.
(3) Dissolving 5 g of chitosan into 1% to obtain an acetic acid solution, then adding 0.8 g of N, N-dimethylformamide solution of ethylenediamine cellulose, adding 0.6 g of chloromethylbenzaldehyde polyethylene glycol, reacting for 8 h at 45 ℃, pouring the solution on a glass plate for casting to form a film after reaction, drying to remove the solvent, and adding the film into deionized water for dipping and washing to obtain the composite film material.
Comparative example 2
(2) Dissolving 2 g of end acyl chloride polyethylene glycol into dichloromethane, adding 0.6 g of 2-hydroxychlorobenzaldehyde and 0.32 g of triethylamine in an ice-water bath, reacting for 2 h, stirring at room temperature for reacting for 12 h, concentrating under reduced pressure after reaction, adding trichloromethane and saturated sodium bicarbonate solution for extraction, drying an organic phase, and washing with diethyl ether to obtain the end chloromethyl benzaldehyde polyethylene glycol.
(3) Dissolving 2 g of chloromethylbenzaldehyde polyethylene glycol into N, N-dimethylformamide, adding 0.045 g of ethyl acetate solution of dodecyl dimethyl tertiary amine, heating to 100 ℃ for reaction for 36 hours, adding ethyl acetate and saturated sodium bicarbonate solution for extraction after the reaction, drying an organic phase, and washing with diethyl ether to obtain the quaternary ammonium salt-terminated benzaldehyde polyethylene glycol.
(3) Dissolving 5 g of chitosan into 1% to obtain an acetic acid solution, then adding 0.4 g of terminal quaternary ammonium salt benzaldehyde polyethylene glycol, reacting for 10 hours at 25 ℃, pouring the solution onto a glass plate for casting to form a film after the reaction, drying to remove the solvent, adding the film into deionized water for dipping and washing to obtain the composite film material.
And (3) bacteriostatic test: using the bacteriostatic loop method, using Escherichia coli as test bacteria, 0.2 mL of 10 6 And (3) adding the CFU/mL escherichia coli bacterial suspension into a culture dish of an agar culture medium, respectively preparing the composite membrane material into membrane materials with the radius of 0.5 mm, then adding the membrane materials into the culture dish, culturing for 24 hours in a constant-temperature incubator at 37 ℃, and determining the diameter of the inhibition zone.
And (3) performing a tensile test on the composite film material by using a universal material testing machine, wherein the tensile rate is 10 cm/min according to GB/T1040-2008, and the composite film sample is 10 cm in length, 1cm in width and 0.5 cm in height.
Claims (7)
1. A biomass antibacterial composite film material comprises ethylene diamine cellulose and chitosan, and is characterized in that: the preparation method of the composite membrane material comprises the following steps: dissolving chitosan into an acetic acid solution, adding an N, N-dimethylformamide solution of ethylenediamine cellulose, adding terminal quaternary ammonium salt benzaldehyde polyethylene glycol, reacting at 25-45 ℃ for 4-10 h, pouring the solution onto a glass plate after reaction, casting to form a film, drying to remove the solvent, adding the film into deionized water, soaking and washing to obtain the biomass antibacterial composite film material.
2. The biomass antibacterial composite film material according to claim 1, characterized in that: the mass ratio of the chitosan, the quadrol cellulose and the terminal quaternary ammonium salt benzaldehyde polyethylene glycol is controlled to be 100:12-30: 5-20.
3. The biomass antibacterial composite film material according to claim 1, characterized in that: the preparation method of the ethylenediamine cellulose comprises the following steps: adding cellulose microcrystal into a sodium hydroxide solution, then adding an ethanol solution of epoxy chloropropane, reacting, adding a product of epoxidized cellulose sodium bicarbonate into a water solution of epoxidized cellulose sodium bicarbonate, and adding ethylenediamine, and reacting to obtain the ethylenediamine cellulose.
4. The biomass antibacterial composite film material according to claim 1, characterized in that: the preparation method of the quaternary ammonium salt-terminated benzaldehyde polyethylene glycol comprises the following steps:
(1) dissolving polyethylene glycol and succinic anhydride into chloroform, then dropwise adding pyridine, and reacting to obtain carboxyl-terminated polyethylene glycol; then dissolving the mixture into N, N-dimethylformamide, dropwise adding thionyl chloride in the nitrogen atmosphere, heating to 40-60 ℃, reacting for 5-12 h, concentrating under reduced pressure to remove the thionyl chloride, and washing a product with diethyl ether to obtain end acyl chloride polyethylene glycol;
(2) dissolving end acyl chloride polyethylene glycol into a reaction solvent, adding 2-hydroxychlorobenzaldehyde and triethylamine in an ice water bath, reacting for 1-2 h, stirring at room temperature for 12-24 h, concentrating under reduced pressure after reaction, adding trichloromethane and saturated sodium bicarbonate solution for extraction, drying an organic phase, and washing with diethyl ether to obtain end chloromethyl benzaldehyde polyethylene glycol;
(3) dissolving chloromethylbenzaldehyde polyethylene glycol into N, N-dimethylformamide, and adding dimethyl tertiary amine (CH) 3 (CH 2 ) n N(CH 3 ) 2 N = 9-17), heating to 80-110 ℃, reacting for 24-48 h, adding ethyl acetate and saturated sodium bicarbonate solution for extraction after the reaction, drying the organic phase, and washing with diethyl ether to obtain the quaternary ammonium salt-terminated benzaldehyde polyethylene glycol.
5. The biomass antibacterial composite film material according to claim 4, characterized in that: the mass ratio of the end acyl chloride polyethylene glycol, the 2-hydroxy chloromethyl benzaldehyde and the triethylamine in the step (2) is controlled to be 100:25-38: 12-20.
6. The biomass antibacterial composite film material according to claim 4, characterized in that: the solvent in the step (2) comprises dichloromethane, trichloromethane, 1, 4-dioxane, tetrahydrofuran and N, N-dimethylformamide.
7. The biomass antibacterial composite film material according to claim 4, characterized in that: the mass ratio of the chloromethylbenzaldehyde polyethylene glycol to the dimethyl tertiary amine in the step (3) is controlled to be 100: 0.8-3.
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| CN115368694A (en) * | 2022-09-30 | 2022-11-22 | 河北百展科技发展有限公司 | Biomass-based reinforced polyvinyl alcohol composite material and preparation method thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115368694A (en) * | 2022-09-30 | 2022-11-22 | 河北百展科技发展有限公司 | Biomass-based reinforced polyvinyl alcohol composite material and preparation method thereof |
| CN115368694B (en) * | 2022-09-30 | 2023-10-13 | 河北百展科技发展有限公司 | Biomass-based reinforced polyvinyl alcohol composite material and preparation method thereof |
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