CN110628089A - Preparation method of poly-gallic acid/chitosan antibacterial material - Google Patents
Preparation method of poly-gallic acid/chitosan antibacterial material Download PDFInfo
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- CN110628089A CN110628089A CN201910963178.9A CN201910963178A CN110628089A CN 110628089 A CN110628089 A CN 110628089A CN 201910963178 A CN201910963178 A CN 201910963178A CN 110628089 A CN110628089 A CN 110628089A
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
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- C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
- C08J2305/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
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- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
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- C08J2405/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2401/00 or C08J2403/00
- C08J2405/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
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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
- C08J2467/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2467/04—Polyesters derived from hydroxy carboxylic acids, e.g. lactones
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Abstract
The invention discloses a preparation method of a polygallic acid/chitosan antibacterial material. Firstly, preparing a buffer solution with the pH value of 4.5; then adding chitosan into the buffer solution, stirring and dissolving; adding gallic acid and laccase into the solution, stirring and dissolving, heating, stirring and reacting for a period of time; adding potassium dihydrogen phosphate and citric acid into the reaction solution, stirring and reacting to obtain a solid-liquid mixture, carrying out suction filtration and washing on the solid-liquid mixture to obtain a filter cake, and drying the filter cake to obtain the poly (gallic acid)/chitosan antibacterial material. The method of the invention obtains the poly-gallic acid/chitosan antibacterial material by citric acid cross-linking gallic acid homopolymer and chitosan, has excellent antibacterial performance, and can be widely applied in the antibacterial industry.
Description
Technical Field
The invention belongs to the field of antibacterial materials, and particularly relates to a preparation method of a poly-gallic acid/chitosan antibacterial material.
Background
With the development of economic globalization, the living standard of people is gradually improved, people have higher requirements on the antibacterial property of the used materials, and the novel antibacterial materials become important guidance for national development.
Chitosan is a natural antibacterial material, is a natural alkaline polysaccharide obtained by deacetylating chitin extracted from shells of animals of the family a, and has been widely studied in recent years. For example, patent CN104906584A compounds chitosan, peppermint oil and glycerol to prepare a biological antibacterial material, which is easily dissolved in an acidic medium and cannot be continuously used; the patent CN107226987A carries out biomass grafting on chitosan to prepare the antibacterial material, and the pig manure is adopted to provide biomass, so that the operation is complicated and the cost is high; CN107383236A grafts cyanamide or dicyandiamide to chitosan, thereby improving the antibacterial property of chitosan, and the incompletely reacted amine compound has great environmental pollution and certain toxicity; patent CN106417275A adopts chitosan to wrap nano-silver graphene oxide to prepare the composite antibacterial material, the graphene is expensive, and the generated antibacterial agent cannot be widely applied.
Gallic acid is tannin acid hydrolysis product, has antibacterial and antiviral effects, and is low in cost. Reports on the preparation of novel antibacterial materials by combining a homopolymer of gallic acid with chitosan have not yet been made.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides a preparation method of a poly-gallic acid/chitosan antibacterial material by taking chitosan and gallic acid as raw materials. The method takes chitin acetylation product chitosan and naturally enriched gallic acid as raw materials, the gallic acid is synthesized by laccase catalysis and self-polymerization, and the gallic acid and the chitosan are crosslinked by citric acid to obtain the gallic acid/chitosan antibacterial material.
The technical scheme adopted by the invention comprises the following steps:
step a: preparing a buffer solution with the pH value of 4.5;
step b: b, adding chitosan into the buffer solution prepared in the step a, and stirring for dissolving;
step c: c, adding gallic acid and laccase into the solution obtained in the step b for dissolving, and then heating and stirring for reaction;
step d: and c, adding citric acid and potassium dihydrogen phosphate into the solution obtained after the reaction in the step c, heating, stirring and reacting to obtain a solid-liquid mixture, carrying out suction filtration and washing on the solid-liquid mixture to obtain a filter cake, and drying the filter cake to obtain the poly (gallic acid)/chitosan antibacterial material.
The buffer solution in the step a) is 2mol/L acetic acid/sodium acetate buffer solution.
The concentration of the chitosan in the step b) is 1.0-5.0 g/L.
The mass ratio of the gallic acid in the step c) to the chitosan in the step b) is 4: 1-1: 4.
The concentration of the citric acid in the step d) is 1.0-5.0 g/L.
And c) heating and stirring for reaction in the step c), heating to 40-60 ℃, and stirring for reaction for 1-10 hours.
And d), heating and stirring for reaction in the step d), heating to 60-80 ℃, and stirring for reaction for 1-10 hours.
In the step b), the viscosity of the added chitosan is 100-200 mpa.s.
The invention has the beneficial effects that:
1) gallic acid is polymerized under the catalysis of laccase to generate water-soluble gallic acid, and the gallic acid is crosslinked with chitosan to form a water-insoluble strong antibacterial agent, so that the defects of poor antibacterial effect of chitosan and the like are overcome.
2) The poly-gallic acid and the chitosan are crosslinked by citric acid to form three-dimensional reticular macromolecules, have strong antibacterial performance, and can be widely applied to the antibacterial industry.
Drawings
FIG. 1 is an antibacterial image of an antibacterial material in example 4 of the present invention
FIG. 2 shows the reaction mechanism of the present invention.
Detailed Description
The invention is further described below with reference to the figures and examples.
According to the method, the poly-gallic acid and the chitosan are crosslinked through the citric acid to obtain the poly-gallic acid/chitosan antibacterial material, and the poly-gallic acid/chitosan antibacterial material has a good inhibition effect on escherichia coli and staphylococcus aureus.
Example 1:
a) 2mol/L of acetic acid/sodium acetate buffer solution with pH value of 4.5 is prepared.
b) 1.0g of chitosan was added to the above 1L of the buffer solution, and dissolved by stirring to obtain a 1.0g/L chitosan solution.
c) And (3) adding gallic acid and laccase into the chitosan solution obtained in the step b) (wherein the mass ratio of the gallic acid to the chitosan is 1:4), stirring for dissolving, heating to 40 ℃, and stirring for reacting for 1 h.
d) Adding monopotassium phosphate and 1g of citric acid into the reaction liquid obtained in the step c), heating to 60 ℃, stirring for reaction for 1 hour, cooling to normal temperature, carrying out suction filtration and washing to obtain a filter cake, and drying the filter cake to obtain the poly (gallic acid)/chitosan antibacterial material X1.
Example 2:
a) 2mol/L of acetic acid/sodium acetate buffer solution with pH value of 4.5 is prepared.
b) 5.0g of chitosan was added to the above 1L of the buffer solution, and dissolved by stirring to obtain a 5.0g/L chitosan solution.
c) And (3) adding gallic acid and laccase into the chitosan solution obtained in the step b) (wherein the mass ratio of the gallic acid to the chitosan is 4:1), stirring for dissolving, heating to 60 ℃, and stirring for reacting for 10 hours.
d) Adding monopotassium phosphate and 5g of citric acid into the reaction liquid obtained in the step c), heating to 80 ℃, stirring for reaction for 10 hours, cooling to normal temperature, carrying out suction filtration and washing to obtain a filter cake, and drying the filter cake to obtain the poly (gallic acid)/chitosan antibacterial material X2.
Example 3:
a) 2mol/L of acetic acid/sodium acetate buffer solution with pH value of 4.5 is prepared.
b) 2.0g of chitosan was added to the above 1L of the buffer solution, and dissolved by stirring to obtain a 2.0g/L chitosan solution.
c) And (3) adding gallic acid and laccase into the chitosan solution obtained in the step b) (wherein the mass ratio of the gallic acid to the chitosan is 2:1), stirring for dissolving, heating to 50 ℃, and stirring for reacting for 3 hours.
d) Adding monopotassium phosphate and 4g of citric acid into the reaction liquid obtained in the step c), heating to 70 ℃, stirring for reacting for 5 hours, cooling to normal temperature, carrying out suction filtration and washing to obtain a filter cake, and drying the filter cake to obtain the poly (gallic acid)/chitosan antibacterial material X3.
Example 4:
a) 2mol/L of acetic acid/sodium acetate buffer solution with pH value of 4.5 is prepared.
b) 2.0g of chitosan was added to the above 1L of the buffer solution, and dissolved by stirring to obtain a 2.0g/L chitosan solution.
c) And (3) adding gallic acid and laccase into the chitosan solution obtained in the step b) (wherein the mass ratio of the gallic acid to the chitosan is 3:2), stirring for dissolving, heating to 50 ℃, and stirring for reacting for 3 hours.
d) Adding monopotassium phosphate and 3.0g of citric acid into the reaction liquid obtained in the step c), heating to 70 ℃, stirring for reaction for 1 hour, cooling to normal temperature, carrying out suction filtration and washing to obtain a filter cake, and drying the filter cake to obtain the poly (gallic acid)/chitosan antibacterial material X4.
Example 5:
a) 2mol/L of acetic acid/sodium acetate buffer solution with pH value of 4.5 is prepared.
b) 4.0g of chitosan was added to the above 1L of the buffer solution, and dissolved by stirring to obtain a 4.0g/L chitosan solution.
c) And (3) adding gallic acid and laccase into the chitosan solution obtained in the step b) (wherein the mass ratio of the gallic acid to the chitosan is 1:2), stirring for dissolving, heating to 40 ℃, and stirring for reacting for 6 hours.
d) Adding monopotassium phosphate and 2g of citric acid into the reaction liquid obtained in the step c), heating to 70 ℃, stirring for reacting for 3 hours, cooling to normal temperature, carrying out suction filtration and washing to obtain a filter cake, and drying the filter cake to obtain the poly (gallic acid)/chitosan antibacterial material X5.
Example 6:
a) 2mol/L of acetic acid/sodium acetate buffer solution with pH value of 4.5 is prepared.
b) 3.0g of chitosan was added to the above 1L of the buffer solution, and dissolved by stirring to obtain a chitosan solution of 3.0 g/L.
c) And (3) adding gallic acid and laccase into the chitosan solution obtained in the step b) (wherein the mass ratio of the gallic acid to the chitosan is 1:3), stirring for dissolving, heating to 50 ℃, and stirring for reacting for 8 hours.
d) Adding monopotassium phosphate and 3g of citric acid into the reaction liquid obtained in the step c), heating to 60 ℃, stirring for reacting for 8 hours, cooling to normal temperature, carrying out suction filtration and washing to obtain a filter cake, and drying the filter cake to obtain the poly (gallic acid)/chitosan antibacterial material X6.
Comparative example 1:
the raw materials and contents and preparation process were the same as in example 4 except that gallic acid was not contained.
Comparative example 2:
pure chitosan powder is adopted as the antibacterial material.
Comparative example 3:
pure gallic acid powder is used as an antibacterial material.
Test example:
each 100 μ L of the extract was taken to have a concentration of 10-7CFU/mL E.coli and 10-7The method comprises the following steps of uniformly coating the CFU/mL staphylococcus aureus on an agar plate, preparing 0.2g of antibacterial materials in the embodiment and the comparative example into a 1.2cm round plate under the pressure of 30MPa, respectively adding the round plates coated with the escherichia coli and the staphylococcus aureus to an agar plate, placing the agar plate in a constant temperature incubator at 37 ℃, and measuring the diameter of a bacteriostatic circle after 24 hours, wherein the diameter of the bacteriostatic circle generated by the antibacterial materials is shown in the table 1:
TABLE 1 color of antibacterial material and size of antibacterial ring formed at antibacterial test
As can be seen from Table 1, the poly (gallic acid)/chitosan antibacterial material obtained by the invention has good antibacterial effect.
As shown in fig. 1, which is an antibacterial image of the antibacterial material of example 4, it can be seen that the antibacterial agent obtained by the present invention has a superior antibacterial effect.
As shown in fig. 2, (a) is a reaction formula of gallic acid self-polymerizing under the catalysis of laccase to generate water-soluble polygallic acid, and (b) is a reaction formula of polygallic acid and chitosan cross-linked by citric acid to form antibacterial agent molecules, and the antibacterial agent molecules are three-dimensional network macromolecular structures.
The applicant declares that the above description is only a specific embodiment of the present invention, but the scope of the present invention is not limited thereto, and it should be understood by those skilled in the art that any changes or substitutions that can be easily conceived by those skilled in the art within the technical scope of the present invention are within the scope and disclosure of the present invention.
Claims (8)
1. A preparation method of a poly-gallic acid/chitosan antibacterial material is characterized in that,
the method comprises the following steps:
step a: preparing a buffer solution with the pH value of 4.5;
step b: b, adding chitosan into the buffer solution prepared in the step a, and stirring for dissolving;
step c: c, adding gallic acid and laccase into the solution obtained in the step b for dissolving, and then heating and stirring for reaction;
step d: and c, adding citric acid and potassium dihydrogen phosphate into the solution obtained after the reaction in the step c, heating, stirring and reacting to obtain a solid-liquid mixture, carrying out suction filtration and washing on the solid-liquid mixture to obtain a filter cake, and drying the filter cake to obtain the poly (gallic acid)/chitosan antibacterial material.
2. The method for preparing the poly-gallic acid/chitosan antibacterial material according to claim 1, wherein the method comprises the following steps: the buffer solution in the step a) is 2mol/L acetic acid/sodium acetate buffer solution.
3. The method for preparing the poly-gallic acid/chitosan antibacterial material according to claim 1, wherein the method comprises the following steps: the concentration of the chitosan in the step b) is 1.0-5.0 g/L.
4. The method for preparing the poly-gallic acid/chitosan antibacterial material according to claim 1, wherein the method comprises the following steps: the mass ratio of the gallic acid in the step c) to the chitosan in the step b) is 4: 1-1: 4.
5. The method for preparing the poly-gallic acid/chitosan antibacterial material according to claim 1, wherein the method comprises the following steps: the concentration of the citric acid in the step d) is 1.0-5.0 g/L.
6. The method for preparing the poly-gallic acid/chitosan antibacterial material according to claim 1, wherein the method comprises the following steps: and c) heating and stirring for reaction in the step c), heating to 40-60 ℃, and stirring for reaction for 1-10 hours.
7. The method for preparing the poly-gallic acid/chitosan antibacterial material according to claim 1, wherein the method comprises the following steps: and d), heating and stirring for reaction in the step d), heating to 60-80 ℃, and stirring for reaction for 1-10 hours.
8. The method for preparing the poly-gallic acid/chitosan antibacterial material according to claim 1, wherein the method comprises the following steps: in the step b), the viscosity of the added chitosan is 100-200 mpa.s.
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Cited By (1)
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| CN113812398A (en) * | 2021-10-11 | 2021-12-21 | 章毅 | Cryogenic freezing method of scaffolds for tissue repair |
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Inventor after: Li Chengcai Inventor after: Luo Yilin Inventor after: Zhang Haoyin Inventor after: Liu Guojin Inventor before: Li Chengcai Inventor before: Guo Yuhai Inventor before: Zhu Hailin Inventor before: Wang Feng Inventor before: Liu Guojin |
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Effective date of registration: 20221014 Address after: 310018 No. 2 street, Baiyang street, Hangzhou economic and Technological Development Zone, Zhejiang 928 Applicant after: ZHEJIANG SCI-TECH University Applicant after: Shanghai Xinghewan Bilingual School Address before: No.928, No.2 street, Jianggan Economic Development Zone, Hangzhou City, Zhejiang Province, 310018 Applicant before: ZHEJIANG SCI-TECH University |