CN110917381A - Bacterial cellulose/polyion liquid antibacterial film and preparation method thereof - Google Patents

Bacterial cellulose/polyion liquid antibacterial film and preparation method thereof Download PDF

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Publication number
CN110917381A
CN110917381A CN201911197588.3A CN201911197588A CN110917381A CN 110917381 A CN110917381 A CN 110917381A CN 201911197588 A CN201911197588 A CN 201911197588A CN 110917381 A CN110917381 A CN 110917381A
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amino acid
choline
bacterial cellulose
ionic liquid
preparation
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贺晓凌
孟红艳
宋浩德
邓时煜
王帅
贺婷婷
魏东盛
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Tianjin Polytechnic University
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
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    • A—HUMAN NECESSITIES
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
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    • A—HUMAN NECESSITIES
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    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
    • A61L15/24—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/46—Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/64—Use of materials characterised by their function or physical properties specially adapted to be resorbable inside the body
    • C—CHEMISTRY; METALLURGY
    • 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
    • C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F120/52—Amides or imides
    • C08F120/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
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    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
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    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
    • A61L2300/602—Type of release, e.g. controlled, sustained, slow

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Abstract

The invention relates to a bacterial cellulose/polyion liquid (BC/PILs) antibacterial film and a preparation method thereof. The preparation method comprises the following steps: (1) preparing bacterial cellulose: the bacterial cellulose gel membrane is prepared by adopting a static culture method and using the cellulose bacteria Komagataeibacter rhaeticus TJPU03 screened and produced in the laboratory. (2) Preparation of Ionic Liquid (ILs) monomers: selecting natural compounds of amino acid and choline to prepare novel green ionic liquid; introducing double bonds into Ionic Liquids (ILs) through acrylic acid (AAc) under the action of N-hydroxysuccinimide (NHS) and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide (EDC) to obtain polymerizable ionic liquid monomers. (3) Preparing a bacterial cellulose/polyion liquid (BC/PILs) antibacterial film: and introducing an ionic liquid monomer into a bacterial cellulose network by adopting in-situ free radical polymerization to prepare the BC/PILs composite membrane. The method is simple and rapid, mild in condition, free of large-scale equipment, green and environment-friendly in aqueous phase reaction, and the obtained composite membrane has good mechanical property, biocompatibility, biodegradability, drug slow-release function and antibacterial property, and has wide application prospects in the fields of biomedicine, tissue engineering and the like.

Description

Bacterial cellulose/polyion liquid antibacterial film and preparation method thereof
Technical Field
The invention relates to the field of microorganisms and materials, in particular to a method for synthesizing a novel composite material by Bacterial Cellulose (BC) and ionic liquid and application thereof.
Background
The BC is a metabolic product synthesized in the growth process of microorganisms, molecular structural units are similar to plant cellulose, and the molecular structural units are high molecular compounds formed by connecting glucose through β -1, 4-glycosidic bonds, and has good biocompatibility, large specific surface area, high water holding rate, good compression performance and tensile performance and high growth controllability.
The Ionic Liquids (ILs) are salts composed of anions and cations and are in a liquid state at room temperature, have the advantages of good thermal stability, low volatility, high conductivity, good solubility and the like, and are widely applied to ion conductive materials, high molecular catalysts, antistatic materials, gas adsorption and separation materials and the like. Polyion liquids (PILs) are polymerized by ionic liquids under certain conditions, have anionic and cationic groups on repeating units, and have the advantages of both the ionic liquids and polymers, and the polyion liquids have certain charges, so that the polyion liquids have certain antibacterial action. Jocobs et al first synthesized quaternary phosphonium salts in 1915, whose antibacterial properties were gradually discovered, and this was the first proposal for broad-sense ionic liquid antibacterial agents. However, ionic liquids in the traditional sense, such as imidazole and pyridine ionic liquids, require a large amount of volatile organic solvents in the synthesis and purification processes, which makes the ionic liquids expensive in manufacturing cost and strong in toxicity, and the traditional ionic liquids themselves have poor biodegradability, not only do not conform to the concepts of sustainable development and green chemistry, but also limit the applications thereof in the medical and biological fields (liu qin, university of south china, 2012).
In order to obtain a more green ionic liquid, the initial raw materials are required to be non-toxic and recyclable, and have lower production cost, so that a biological renewable resource is developed, and the ionic liquid is synthesized by adopting natural products or derivatives thereof as the raw materials, so that the safety of the ionic liquid is improved, and meanwhile, some new functions are endowed. For example, Petkovic et al synthesized nine ionic liquids using choline bicarbonate and an organic acid. Choline bicarbonate is a non-toxic strong base that readily undergoes neutralization with various acids to form the corresponding choline salt. The choline salt can be biologically used and can be completely degraded by oxygen. The organic acid as the anion has convenient source and low cost, and only water is introduced as a solvent in the whole synthesis process, thereby not only being green and saving time, but also having low cost. Compared with conventional ionic liquids, such ionic liquids exhibit very low toxicity, which is two orders of magnitude lower than common imidazole and pyridine ions (m.petkovic, j.l.ferguson, Green chem., 2010.12.643-649). The amino acid contains carboxylic acid and amino group, is natural zwitterion, and most of the amino acid can be subjected to neutralization reaction with choline to obtain the choline amino acid ionic liquid with low toxicity and good degradability. According to the invention, double bonds are introduced into a choline amino acid ionic liquid molecular structure through molecular modification, the BC is used as a base material, and ionic liquid is introduced into a BC three-dimensional network to prepare the composite membrane, and the composite membrane is applied to the aspects of antibacterial materials and wound dressings.
Disclosure of Invention
The invention aims to provide a BC/PILs antibacterial film. Choline amino acid ionic liquid and BC are compounded to prepare the non-toxic and degradable biomedical material with antibacterial and drug slow-release functions.
The invention also aims to provide a preparation method of the BC/PILs antibacterial film, which comprises the following steps: (1) the BC are cultured and purified using a fermentation medium. (2) The choline amino acid ionic liquid monomer is prepared through the neutralization reaction of amino acid and choline. (3) The amino and carboxyl are dehydrated and condensed into amido bond, so that the choline amino acid ionic liquid and the acrylic acid are synthesized into the polymerizable vinyl choline amino acid ionic liquid. (4) The vinyl ionic liquid monomer enters the BC network by an impregnation method, and an initiator is added to polymerize in the BC to form the BC/PILs composite membrane.
Advantageous effects
The invention has the advantages that:
(1) the BC/PILs composite membrane provided by the invention has the advantages of BC and polyion liquid, has good mechanical property, hygroscopicity, biocompatibility, biodegradability, antibacterial property and drug slow release property, can be used as a wound dressing and a drug slow release carrier, and has high practical application value in the field of biomedicine.
(2) The preparation method of the BC/PILs composite membrane provided by the invention is simple and rapid, mild in condition, free of large-scale equipment, green and environment-friendly in aqueous phase reaction, and convenient to popularize.
Detailed Description
The present invention is further illustrated in detail by the following examples, which are provided only for the purpose of explaining the present invention and are not intended to limit the scope of the present invention. The experimental methods used in the following examples are all conventional methods unless otherwise specified; the materials, reagents and the like used are, unless otherwise specified, commercially available reagents and materials.
Example 1 preparation and purification of bacterial cellulose
Firstly, 100mL of fermentation medium was poured into a 250mL conical flask, the formula of the fermentation medium is shown in Table 1, the conical flask was placed in a sterilizer and autoclaved at 121 ℃ for 30min, and 2mL of absolute ethanol was added after cooling. Inoculating Komagataeibacter rhaeticus TJPU03 bacteria screened in the laboratory into a culture medium, statically culturing for 7 days, taking out the BC membrane, putting the BC membrane into a 1% w/v sodium hydroxide solution, heating in a water bath at 80 ℃ for 2 hours to remove residual culture medium and thalli, and finally repeatedly cleaning with distilled water to be neutral to obtain the purified BC membrane.
TABLE 1 fermentation Medium formulation
Figure BSA0000195861670000031
EXAMPLE 2 Synthesis of Choline amino acid Ionic Liquids (ILs)
The ratio of choline to amino acids (mol: mol) was 1: 1.05. Weighing 1mol of amino acid, adding 5mL of deionized water, uniformly stirring, putting into a round-bottom flask, and placing in an ice water bath at 3 ℃. 1.2118g of choline is weighed and added with 5mL of deionized water, after uniform mixing, the choline is dripped into the amino acid solution by a constant pressure dropping funnel, 2-3 drops are dripped at each second most suitably, after the dripping is finished, the round bottom flask is plugged by a glass stopper, and the mixture reacts for 48 hours in an ice-water bath environment at the temperature of 3 ℃. And (3) carrying out rotary evaporation after the reaction is finished for 48 hours, wherein the set conditions are that the rotating speed is 120r/min, the temperature is 55 ℃, and the choline-amino acid ionic liquid can be obtained after the rotary evaporation. The amino acids are: phenylalanine, tryptophan, isoleucine, proline, serine, and glycine.
Example 3 preparation of vinyl Choline amino acid Ionic liquids
The amino and carboxyl generate amido bond, so that choline amino acid and acrylic acid are synthesized into polymerizable vinyl choline amino acid ionic liquid. The dosage of the medicine is based on 0.01mol of acrylic acid (AAc), 0.7206g of acrylic acid after removing a polymerization inhibitor through reduced pressure distillation is weighed, 5mL of deionized water is added, a magnetic stirrer is used for stirring uniformly, 0.2302g N-hydroxysuccinimide (the molar ratio of the hydroxysuccinimide to the AAc is 0.2: 1) and 0.3834g of EDC (the molar ratio of the EDC to the AAc is 1: 1) are weighed and added into a reaction system, the magnetic stirrer is used for stirring reaction for 2 to 3 hours, choline amino acid ionic liquid (the molar ratio of the choline amino acid ionic liquid to the AAc is 1: 1) is added, and the stirring is continued for about 1 hour by the magnetic stirrer. A total of 1.917g of EDC was added in 5 portions, each of 0.3834g, and the reaction was continued for 12h after all the EDC had been added. And after 12h, carrying out rotary evaporation operation on the reaction liquid, wherein the rotary evaporation conditions are 120r/min and 55 ℃, and the viscous liquid obtained after the rotary evaporation is finished is the vinyl choline amino acid ionic liquid. The amino acids are: phenylalanine, tryptophan, isoleucine, proline, serine, and glycine.
EXAMPLE 4 preparation of PILs/BC composite membranes
Cutting the purified BC membrane into small blocks of 1cm multiplied by 1cm, respectively placing the small blocks in aqueous solutions of vinyl choline amino acid ionic liquid monomers with different types and different concentrations, and adding the aqueous solutions in N2Heating the mixture to 60 ℃ in a water bath under protection, magnetically stirring the mixture for 6 hours, and adding a KPS initiator to initiate vinyl choline amino acid ionic liquid monomer to perform polymerization reaction inside the BC network. And after reacting for 10h, cleaning the surface of the composite membrane by using distilled water, storing the composite membrane in a low-temperature refrigerator at the temperature of-20 ℃ for 10h, and finally drying the composite membrane in a freeze dryer for 24h to obtain the PLIs/BC composite membrane. The concentration of the vinyl choline amino acid ionic liquid is 0.1g/mL, 0.3g/mL, 0.5g/mL and 0.7 g/mL.

Claims (6)

1. The bacterial cellulose/polyion liquid antibacterial film and the preparation method thereof are characterized in that the obtained composite film has good mechanical property, biocompatibility, biodegradability, drug slow release function and antibacterial property, and has wide application prospect in the fields of biomedicine, tissue engineering and the like.
2. The method for preparing the bacterial cellulose/polyion liquid antibacterial film according to claim 1, comprising the following steps:
(1) preparation and purification of bacterial cellulose
Pouring 100mL of fermentation culture solution into a 250mL conical flask, placing the conical flask into a sterilizing pot, autoclaving at 121 ℃ for 30min, cooling, and adding 2mL of absolute ethyl alcohol. Inoculating Komagataeibacter rhaeticus TJPU03 bacteria screened in a laboratory into a culture medium, statically culturing for 7 days, taking out the BC membrane, putting the BC membrane into a 1% w/v sodium hydroxide solution, heating in a water bath at 80 ℃ for 2 hours to remove residual culture medium and thalli, and finally repeatedly cleaning with distilled water to be neutral to obtain a purified BC membrane;
(2) synthesis of Choline amino acid Ionic Liquids (ILs)
The ratio of choline to amino acids (mol: mol) was 1: 1.05. Weighing 1mol of amino acid, adding 5mL of deionized water, uniformly stirring, putting into a round-bottom flask, and placing in an ice water bath at 3 ℃. 1.2118g of choline is weighed and added with 5mL of deionized water, after uniform mixing, the choline is dripped into the amino acid solution by a constant pressure dropping funnel, 2-3 drops are dripped at each second most suitably, after the dripping is finished, the round bottom flask is plugged by a glass stopper, and the mixture reacts for 48 hours in an ice-water bath environment at the temperature of 3 ℃. After the reaction is finished for 48 hours, carrying out rotary evaporation under the set conditions of the rotating speed of 120r/min and the temperature of 55 ℃, and obtaining the choline-amino acid ionic liquid after the rotary evaporation;
(3) preparation of vinyl choline amino acid ionic liquid
The dosage of the medicine is based on 0.01mol of acrylic acid (AAc), 0.7206g of acrylic acid after removing a polymerization inhibitor through reduced pressure distillation is weighed, 5mL of deionized water is added, a magnetic stirrer is used for stirring uniformly, 0.2302g N-hydroxysuccinimide (the molar ratio of the hydroxysuccinimide to the AAc is 0.2: 1) and 0.3834g of EDC (the molar ratio of the EDC to the AAc is 1: 1) are weighed and added into a reaction system, the magnetic stirrer is used for stirring reaction for 2 to 3 hours, choline amino acid ionic liquid (the molar ratio of the choline amino acid ionic liquid to the AAc is 1: 1) is added, and the stirring is continued for about 1 hour by the magnetic stirrer. Adding 1.917g of EDC for 5 times, wherein 0.3834g of EDC is added each time, reacting for 12h after all EDC is added, and performing rotary evaporation operation on the reaction solution after 12h, wherein the rotary evaporation conditions are 120r/min and 55 ℃, and the viscous liquid obtained after the rotary evaporation is the vinyl choline amino acid ionic liquid;
(4) preparation of PILs/BC composite membrane
Cutting the purified BC membrane into small blocks of 1cm multiplied by 1cm, respectively placing the small blocks in aqueous solutions of vinyl choline amino acid ionic liquid monomers with different types and different concentrations, and adding the aqueous solutions in N2Heating the mixture to 60 ℃ in a water bath under protection, magnetically stirring the mixture for 6 hours, and adding a KPS initiator to initiate vinyl choline amino acid ionic liquid monomer to perform polymerization reaction inside the BC network. And after reacting for 10h, cleaning the surface of the composite membrane by using distilled water, storing the composite membrane in a low-temperature refrigerator at the temperature of-20 ℃ for 10h, and finally drying the composite membrane in a freeze dryer for 24h to obtain the PLIs/BC composite membrane.
3. The bacterial cellulose/polyion liquid antibacterial film according to claim 1, wherein the obtained composite film has good mechanical properties, biocompatibility, biodegradability, drug slow release function and antibacterial property.
4. The method for preparing the bacterial cellulose/polyion liquid antibacterial film according to claim 2, wherein the amino acids are: phenylalanine, tryptophan, isoleucine, proline, serine, and glycine.
5. The method for preparing a bacterial cellulose/polyion liquid antibacterial film according to claim 2, wherein the concentration of the vinyl choline amino acid ionic liquid is 0.1g/mL, 0.3g/mL, 0.5g/mL, 0.7 g/mL.
6. The method for preparing a bacterial cellulose/polyion liquid antibacterial film according to claim 2, wherein the bacterial cellulose is produced by Komagataeibacter rhaeticus TJPU03 screened by the laboratory.
CN201911197588.3A 2019-11-29 2019-11-29 Bacterial cellulose/polyion liquid antibacterial film and preparation method thereof Pending CN110917381A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115624651A (en) * 2022-09-30 2023-01-20 中国人民解放军军事科学院军事医学研究院 Adhesive ionic conductive hydrogel patch and preparation method thereof
CN116333565A (en) * 2023-03-02 2023-06-27 四川大学 Method for preparing three-component antibacterial coating by choline amino acid ionic liquid

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115624651A (en) * 2022-09-30 2023-01-20 中国人民解放军军事科学院军事医学研究院 Adhesive ionic conductive hydrogel patch and preparation method thereof
CN116333565A (en) * 2023-03-02 2023-06-27 四川大学 Method for preparing three-component antibacterial coating by choline amino acid ionic liquid
CN116333565B (en) * 2023-03-02 2024-05-17 四川大学 Method for preparing three-component antibacterial coating by choline amino acid ionic liquid

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Application publication date: 20200327