CN109134754A - A kind of antibacterial micro-nano particle and its preparation method and application having adhesive function - Google Patents
A kind of antibacterial micro-nano particle and its preparation method and application having adhesive function Download PDFInfo
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- CN109134754A CN109134754A CN201810825106.3A CN201810825106A CN109134754A CN 109134754 A CN109134754 A CN 109134754A CN 201810825106 A CN201810825106 A CN 201810825106A CN 109134754 A CN109134754 A CN 109134754A
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- nano particle
- adhesive function
- preparation
- antibacterial
- antibacterial micro
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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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/30—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
-
- 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
- C08F220/00—Copolymers 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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/40—Esters of unsaturated alcohols, e.g. allyl (meth)acrylate
-
- 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
- C08F220/00—Copolymers 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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
Abstract
The invention discloses a kind of preparation methods of antibacterial micro-nano particle for having adhesive function, by monomer dopamine Methacrylamide and monomer eugenol methacrylate, under the initiation of initiator azodiisobutyronitrile, the antibacterial micro-nano particle of tool adhesive function is prepared in reaction in the mixed solution system of ethanol/water.Prepared antibacterial granule antibacterial effect is excellent.The micro-nano particle is expected to be used to improve the antibiotic property of biomaterial as antimicrobial coating, achievees the effect that effectively to stick and long acting antibiotic.This improves people's life and is of great significance to control bacterium infection.
Description
Technical field
The invention belongs to anti-biotic material field, be related to a kind of antibacterial micro-nano particle for having adhesive function and preparation method thereof and
Using.
Background technique
The antibiotic property for improving biomaterial surface is particularly significant, because can usually cause in the implantation process of biomaterial
Bacterium infection, this causes serious harm to people's health.There are many strategies for improving biomaterial antibiotic property, usually passes through
Research bacterium causes the process of infection to construct antibacterial strategy.Costerton etc. is the study found that bacterium attaches to material table first
Then face attracts similar bacterial accumulation by secretion signal molecule, when the concentration of signaling molecule increases to certain level, bacterium
Cell is induced and secrets out of the protein ingredient for constituting extracellular matrix, until ultimately forming biomembrane.Then, biomembrane is gradually
Maturation forms cavity and releases planktonic bacteria, causes new process, forms infection.The bacterium that is formed as of biomembrane provides one
A protective layer makes bacterium in film be able to maintain cell activity, and the antibacterial material outside film can not contact, and cause in biomembrane
The resistivity of bacteria agent and human immune system greatly enhance, thus become bacterium infection related with biomaterial
Refractory arch-criminal more.It is therefore prevented that biomaterial surface, which forms bacterial biof iotalm, becomes improvement biomaterial anti-microbial property
Key, and the first step of biofilm formation is bacterium sticking on the surface of the material, so preventing bacterium from sticking on the surface of the material
Bacterium infection can effectively be inhibited.Hydrophilic and hydrophobic by changing biomaterial ontology or surface can effectively inhibit bacterium viscous
Attached, main material has polyethylene glycol, amphoteric ion polymer etc., inhibits bacterium glutinous and forming hydration layer on the surface of the material
It is attached.Since sticking for minute quantity bacterium can cause rapidly the formation of biomembrane, so more common strategy is on the surface of the material
Grafting or is loaded into antibacterial material at antibacterial group in the material, can kill rapidly stick it is a large amount of thin with surrounding materials on the surface of the material
Bacterium prevents the generation of infection.A large number of studies show that the group with positive charge can assign material good antibacterial property, such as surface
Rich amino-containing spermidine quantum dot, amino modified cellulose etc..Common antibacterial material includes inorganic silver, zinc oxide
Deng organic synthesis class quaternary ammonium salt, halogen amine etc. and natural class chitosan, antibacterial peptide, eugenol etc..Wherein, eugenol is from plant
A kind of natural antibacterial agent extracted in object cloves, excellent antibacterial is all had to Gram-negative bacteria and gram-positive bacteria
Property.Compared to the longer antibacterial agent of the research histories such as quaternary ammonium salt, chitosan, the research about eugenol is less, it is therefore necessary to
It is furtherd investigate.
Summary of the invention
In view of this, in order to achieve the above objectives, the present invention provides following technical side the purpose of the present invention is to provide one kind
Case:
The beneficial effects of the present invention are: with dopamine Methacrylamide (DMA) for monomer, introduce eugenol methyl-prop
Olefin(e) acid ester (EMA) is prepared for the copolymerization micro-nano particle (P (DMA-co-EMA)) of DMA and EMA, the micro-nano particle as second comonomer
With pervasive Adhesion property, and the micro-nano particle can be used as antimicrobial coating for improving the antibiotic property of biomaterial, reach
Effectively stick the effect with long acting antibiotic, especially there is excellent antibacterial effect to Gram-negative bacteria.This is to control bacterium
Infection improves people's life and is of great significance.
Detailed description of the invention
In order to keep the purpose of the present invention, technical scheme and beneficial effects clearer, the present invention provides following attached drawing and carries out
Illustrate:
Fig. 1 is the synthetic route chart of P (DMA-co-EMA) copolymer.
The SEM image of P (DMA-co-EMA) when Fig. 2 is different EMA/DMA ratios.
Fig. 3 is P (DMA-co-EMA) adhesion effect figure.
Fig. 4 is P (DMA-co-EMA) antibacterial effect figure.
Specific embodiment
Below in conjunction with attached drawing, a preferred embodiment of the present invention will be described in detail.
As shown in Figure 1, by monomer dopamine Methacrylamide and monomer eugenol methacrylate, in initiator idol
Under the initiation of nitrogen bis-isobutyronitrile, the antibacterial micro-nano of tool adhesive function is prepared in reaction in the mixed solution system of ethanol/water
Particle.
Embodiment 1
1, the synthesis of dopamine Methacrylamide (DMA)
Weigh 10g Boratex, 4g sodium carbonate be dissolved in 100mL deionized water be added 250mL three-necked flask in, stirring and dissolving,
Boratex and sodium carbonate supersaturation.Nitrogen is bubbled 20min and eliminates the oxygen in solution, and 5g dopamine hydrochloride is added and continues to stir
To dissolution.4.7mL methacrylic anhydride is dissolved in after 25mL tetrahydrofuran and is slowly added dropwise into three-necked flask, 1M hydrogen is used after dripping
Sodium oxide molybdena adjusts pH to 8 or more, to protect the phenolic hydroxyl group of dopamine.Ventilatory response 14h is stirred at room temperature, products therefrom is that white is outstanding
Supernatant liquid.It post-processes as follows: reaction product is filtered to extra salt, then adjust PH to 2 with 6M salt, then use 50mL acetic acid
Ethyl ester extracts 3 times to obtain yellow organic layer, and clarification organic layer, revolving to 25mL or so, stirring are filtered to obtain after anhydrous magnesium sulfate is dry
Under be slowly added dropwise into 250mL n-hexane, obtain grey suspension, put the crystallization of 4 DEG C of refrigerator cold-storages.The next day filter, naturally dry, product
For grey powder, it is spare to collect product sealing refrigeration.
2, the synthesis of eugenol methacrylate (EMA)
It weighs 6.56g eugenol and 4.04g triethylamine is dissolved in 100mL ether and is added in 250mL three-necked flask, nitrogen is bubbled
20min deoxygenation.Under ice bath, it is slowly added dropwise after 4.7g methacrylic chloride is dissolved in 25mL ether into reaction flask.It is stirred at room temperature logical
Solid/liquid/gas reactions 48h, reaction products therefrom are yellow suspension.Post-process as follows: reaction solution is removed by filtration triethylamine hydrochloride, then
It is respectively washed 3 times with 5% sodium hydroxide solution and deionized water respectively, anhydrous magnesium sulfate is dry, rotates to obtain product, product is yellow
Liquid.
3, the synthesis of DMA and EMA copolymer p (DMA-co-EMA)
The total amount of fixed DMA and EMA is 0.1mol/L, and solvent is the total 10mL of 1/9 mixed solvent of ethanol/water volume ratio.Claim
It takes appropriate DMA and EMA in 10mL polymerization pipe, is evacuated deoxygenation 20min, sealing.It weighs 0.0033g AIBN and is dissolved in 10mL ethyl alcohol, lead to
It takes 1mL initiator solution that polymerization pipe is added under nitrogen protection after gas 20min, after reactant is completely dissolved, continues in nitrogen
9mL is added under protection into polymerization pipe to have ventilated the deionized water of 20min, is uniformly mixed, standing reaction 8h is protected from light at 70 DEG C.Afterwards
It handles as follows: reaction product being precipitated in the 50mL centrifuge tube for filling 40mL deionized water, is centrifuged several times, remove supernatant
Liquid, deposit are freeze-dried for 24 hours, and final product is white powder.In order to probe into influence of the EMA/DMA ratio to reaction, design
A series of experiments, specific experiment design such as table 1.
The dosage of monomer and initiator when 1 difference EMA/DMA ratio of table
From figure 2 it can be seen that the yield and partial size of polymer particle gradually increase with the increase of second comonomer EMA,
And its pattern has significant change.After second comonomer EMA is added, the size of copolymer p (DMA-co-EMA) is obviously than DMA homopolymerization
The size of object PDMA is small.This is because EMA hydrophobicity is stronger compared with the precipitation polymerization of DMA, so that the copolymerization of DMA and EMA
Solubility ratio DMA homopolymer of the object in system is low, can form a large amount of primary stable nucleus within a short period of time, and primary is stablized
The partial size that nucleus number purpose increase inevitably results in final particle reduces.It is n/n:=3/ that Fig. 2, which respectively illustrates EMA/DMA amount ratio,
7,5/5 and 7/3 when polymer beads SEM image.Obviously, polymer particle morphology is influenced less when EMA additional amount is less,
It is more regular to scheme ball-type under a-b system, and with the increase of EMA, particle size slightly reduces.It, can be by when EMA is continued growing
Gradually influence the regularity (as shown in Figure 2 c) of polymer particle, thus it is speculated that be because the hydrophobicity of polymer particle increases, so that greatly
Weight polymers particle buildup.Meanwhile discovery is tested when it is 10/0 (V/V) that EMA, which continues to increase to EMA/DMA ratio, cannot
It obtains polymer particle and generates block.To sum up, at monomer ratio EMA/DMA=5/5 (n/n), pattern rule can be obtained
Whole polymer microballoon.
Embodiment 2
The total amount of fixed DMA and EMA is 0.15mol/L, and solvent is the total 10mL of 5/5 mixed solvent of ethanol/water volume ratio.Claim
It takes appropriate DMA and EMA in 10mL polymerization pipe, is evacuated deoxygenation 20min, sealing.It weighs 0.00656g AIBN and is dissolved in 10mL ethyl alcohol,
It takes 1mL initiator solution that polymerization pipe is added under nitrogen protection after ventilation 20min, after reactant is completely dissolved, continues in nitrogen
9mL is added under gas shielded into polymerization pipe to have ventilated the deionized water of 20min, is uniformly mixed, standing reaction is protected from light at 80 DEG C
10h.It post-processes as follows: reaction product being precipitated in the 50mL centrifuge tube for filling 40mL deionized water, is centrifuged several times, remove
Supernatant, deposit are freeze-dried for 24 hours, and final product is white powder.
Embodiment 3
The total amount of fixed DMA and EMA is 0.08mol/L, and solvent is the total 10mL of 1/10 mixed solvent of ethanol/water volume ratio.
Appropriate DMA and EMA are weighed in 10mL polymerization pipe, is evacuated deoxygenation 20min, sealing.It weighs 0.00495g AIBN and is dissolved in 10mL second
Alcohol, ventilate 20min after take 1mL initiator solution that polymerization pipe is added under nitrogen protection, after reactant is completely dissolved, continue exist
9mL is added under nitrogen protection into polymerization pipe to have ventilated the deionized water of 20min, is uniformly mixed, standing reaction is protected from light at 75 DEG C
6h.It post-processes as follows: reaction product being precipitated in the 50mL centrifuge tube for filling 40mL deionized water, is centrifuged several times, remove
Supernatant, deposit are freeze-dried for 24 hours, and final product is white powder.
The test of 4 Adhesion property of embodiment
Titanium sheet is cut into the specification of 1.5cm × 1.5cm, with deionized water, dehydrated alcohol, each ultrasound 10min of acetone with
Titanium plate surface is cleaned, it is spare with being dried with nitrogen.It weighs the polymer beads 20mg that R3 scheme in embodiment 1 obtains and is scattered in 10mL
In ethyl alcohol, clean titanium sheet is respectively put into each suspension, for 24 hours, clean titanium sheet does blank control to stirring at normal temperature.Use deionized water
Titanium sheet is rinsed respectively with ethyl alcohol, is dried with nitrogen, and by scanning electron microscopic observation titanium plate surface pattern, whether polymer beads are adhered to
In titanium sheet.
Fig. 3 respectively illustrates the SEM image of pure titanium plate surface and has sticked the surface SEM of the titanium sheet of P (DMA-co-EMA)
Image (figure b is microcosmic, figure c macroscopic view).As seen from the figure, pure titanium plate surface is smooth clean (as shown in Figure 3a).And in contrast, surface
Stick the titanium plate surface (as shown in Figure 3b) for having P (DMA-co-EMA), it can be clearly seen that polymer beads illustrate polymer particles
Grain is successfully attached to titanium plate surface, and keeps ball-type.
5 anti-microbial property test of embodiment
The anti-microbial property of P (DMA-co-EMA) is evaluated by measurement minimum inhibitory concentration (MIC), selects Gram-negative
Bacterium Escherichia coli (E.coli) are experimental strain.Experiment has carried out the reality of minimum inhibitory concentration by experimental strain of Escherichia coli
It tests, experimental result is as shown in Figure 4.Figure 4, it is seen that the concentration that a-f respectively illustrates P (DMA-co-EMA) is respectively
Antibacterial experiment when 40,20,10,5,2.5,0mg/mL is as a result, as seen from the figure, compared with control group f, P (DMA-co-EMA) is to big
Enterobacteria has good antibacterial effect, and with the increase of P (DMA-co-EMA) concentration, fungistatic effect enhancing.
Finally, it is stated that preferred embodiment above is only used to illustrate the technical scheme of the present invention and not to limit it, although logical
It crosses above preferred embodiment the present invention is described in detail, however, those skilled in the art should understand that, can be
Various changes are made to it in form and in details, without departing from claims of the present invention limited range.
Claims (10)
1. a kind of preparation method for the antibacterial micro-nano particle for having adhesive function, which is characterized in that by monomer dopamine metering system
Amide and monomer eugenol methacrylate, under the initiation of initiator azodiisobutyronitrile, in the mixed solution of ethanol/water
The antibacterial micro-nano particle of tool adhesive function is prepared in reaction in system.
2. a kind of preparation method of antibacterial micro-nano particle for having adhesive function according to claim 1, which is characterized in that institute
The total concentration for stating monomer is 0.08~0.15mol/L, and the volume ratio of the second alcohol and water is 5:5~1:10, and the initiator is dense
Degree is the 2%~4% of monomer molar amount.
3. a kind of preparation method of antibacterial micro-nano particle for having adhesive function according to claim 1, which is characterized in that institute
It is 1:9 that the total concentration for stating monomer, which is the volume ratio of second alcohol and water described in 0.1mol/L, and the initiator concentration is monomer molar amount
2%.
4. a kind of preparation method of antibacterial micro-nano particle for having adhesive function according to claim 1, which is characterized in that institute
The molar ratio for stating dopamine Methacrylamide and eugenol methacrylate is 1:1.
5. a kind of preparation method of antibacterial micro-nano particle for having adhesive function according to claim 1, which is characterized in that institute
It states reaction and first carries out deoxygenation before start, and be carried out in the dark under inert gas protection.
6. a kind of preparation method of antibacterial micro-nano particle for having adhesive function according to claim 1, which is characterized in that institute
The condition for stating reaction is that 6h~10h is reacted at 70 DEG C~80 DEG C.
7. a kind of preparation method of antibacterial micro-nano particle for having adhesive function according to claim 1, which is characterized in that institute
It states and after reaction precipitates product in water, deposit freeze-drying.
8. a kind of preparation method of the antibacterial micro-nano particle of -7 any tool adhesive functions is prepared according to claim 1
Tool adhesive function antibacterial micro-nano particle.
9. a kind of application of the antibacterial micro-nano particle for having adhesive function as claimed in claim 8 on anti-Gram-negative bacteria.
10. application as claimed in claim 9, which is characterized in that the Gram-negative bacteria is Escherichia coli.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113549414A (en) * | 2021-08-11 | 2021-10-26 | 福建农林大学 | Preparation method of environment-friendly nano-cellulose crosslinked dopa adhesive |
| CN113925060A (en) * | 2021-09-13 | 2022-01-14 | 浙江理工大学 | Nano ZnO loaded antibacterial polymer and preparation method and application thereof |
| CN114712569A (en) * | 2022-04-08 | 2022-07-08 | 中山大学附属第八医院（深圳福田） | Renewable antibacterial bone-promoting titanium-based metal material and preparation method and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103265657A (en) * | 2013-05-27 | 2013-08-28 | 德州学院 | Method for preparing monodisperse polymer microspheres by photo-initiation precipitation polymerization |
| CN103755870A (en) * | 2014-01-06 | 2014-04-30 | 苏州大学 | Dopamine-containing random copolymer, and fine preparation method and application thereof |
| CN106565912A (en) * | 2016-11-11 | 2017-04-19 | 广州大学 | Polyquaternium polymer emulsion antibacterial agent, preparation method thereof and application thereof |
| CN106631942A (en) * | 2016-12-08 | 2017-05-10 | 中国科学院宁波材料技术与工程研究所 | Eugenol-based UV (ultraviolet) optical resin monomer and preparation method and application thereof |
-
2018
- 2018-07-25 CN CN201810825106.3A patent/CN109134754B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103265657A (en) * | 2013-05-27 | 2013-08-28 | 德州学院 | Method for preparing monodisperse polymer microspheres by photo-initiation precipitation polymerization |
| CN103755870A (en) * | 2014-01-06 | 2014-04-30 | 苏州大学 | Dopamine-containing random copolymer, and fine preparation method and application thereof |
| CN106565912A (en) * | 2016-11-11 | 2017-04-19 | 广州大学 | Polyquaternium polymer emulsion antibacterial agent, preparation method thereof and application thereof |
| CN106631942A (en) * | 2016-12-08 | 2017-05-10 | 中国科学院宁波材料技术与工程研究所 | Eugenol-based UV (ultraviolet) optical resin monomer and preparation method and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| B. L. WANG ET AL.: "Bio-inspired terpolymers containing dopamine,cations and MPC: a versatile platform to construct a recycle antibacterial and antifouling surface", 《JOURNAL OF MATERIALS CHEMISTRY B》 * |
| XIN WANG ET AL.: "Diblock copolymer containing bioinspired borneol and dopamine moieties: Synthesis and antibacterial coating applications", 《POLYMER》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113549414A (en) * | 2021-08-11 | 2021-10-26 | 福建农林大学 | Preparation method of environment-friendly nano-cellulose crosslinked dopa adhesive |
| CN113925060A (en) * | 2021-09-13 | 2022-01-14 | 浙江理工大学 | Nano ZnO loaded antibacterial polymer and preparation method and application thereof |
| CN114712569A (en) * | 2022-04-08 | 2022-07-08 | 中山大学附属第八医院（深圳福田） | Renewable antibacterial bone-promoting titanium-based metal material and preparation method and application thereof |
| CN114712569B (en) * | 2022-04-08 | 2023-06-02 | 中山大学附属第八医院（深圳福田） | Renewable antibacterial bone titanium-based metal material and preparation method and application thereof |
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