CN105776179B - A kind of water soluble quaternary ammonium salinization Nano carbon balls and preparation method and application - Google Patents
A kind of water soluble quaternary ammonium salinization Nano carbon balls and preparation method and application Download PDFInfo
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- CN105776179B CN105776179B CN201610251237.6A CN201610251237A CN105776179B CN 105776179 B CN105776179 B CN 105776179B CN 201610251237 A CN201610251237 A CN 201610251237A CN 105776179 B CN105776179 B CN 105776179B
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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
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
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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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
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- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/01—Particle morphology depicted by an image
- C01P2004/03—Particle morphology depicted by an image obtained by SEM
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- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/30—Particle morphology extending in three dimensions
- C01P2004/32—Spheres
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/51—Particles with a specific particle size distribution
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/60—Particles characterised by their size
- C01P2004/64—Nanometer sized, i.e. from 1-100 nanometer
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Abstract
The invention discloses a kind of water soluble quaternary ammonium salinization Nano carbon balls, and it is made by band amino high-molecular compound and alkyl betaine reaction, including the Nano carbon balls being mainly made up of carbon and the alkyl betaine for being grafted on Nano carbon balls surface.The invention also discloses the preparation method of foregoing water soluble quaternary ammonium salinization Nano carbon balls and the application in antibiosis.Compared with prior art; the present invention completes chemical graft and carbon nano-particle with amino high-molecular compound and alkyl betaine by the step of hydro-thermal method one, and obtained Nano carbon balls have good water-soluble, relatively low cytotoxicity and excellent broad spectrum antibacterial performance.
Description
Technical field
The invention belongs to field of nanometer technology, and in particular to a kind of water soluble quaternary ammonium salinization Nano carbon balls and preparation method thereof
With application.
Background technology
Carbon is one of most important and human relation's element the closest present in nature.Nearest more than ten
Year since, it is all kinds of with excellent properties carbon nanomaterial (such as CNT, carbon nano-fiber, Nano carbon balls, carbon quantum dot,
Graphene and fullerene etc.) cause the extensive concern of people.Biocompatible carbon material is good, raw material is inexpensive, can largely obtain
Obtain and structure and property are various, have been widely used for material modification, the energy, catalysis, environmental protection, electronic device, load medicine and life
The fields such as thing imaging.
And nano material is also gradually to rise in the development of antibiosis, mainly include two major classes：The first kind is by receiving
Rice grain itself produces inhibitory action to bacterium, specifically includes：(1) carbon nanomaterial, such as graphene；(2) single metal and
Metal oxide nanoparticles, such as gold, silver, titanium dioxide, zinc oxide, calcium oxide, cupric oxide, copper sulfide, magnesia nanometer
Particle etc.；(3) metal pairing gold nano grain, such as electrum, plation, silver-colored cobalt alloy, CTB alloy nano particle.
Second class is by being grafted the antimicrobial molecules such as antibiotic so that nano particle has antibacterial functions, and can improve the effect of antibiotic
Can and increase antibacterial effect or to antibacterial resistance etc., such as gold or silver nano-grain are grafted Amoxicillin antibiotic, single wall
CNT is grafted lysozyme and vancomycin modification silica etc..But such grafting is generally limited by nanometer
Functional group and antibiotic on particle, difficult, complex steps are prepared, and the steady of nano particle can be substantially reduced after modification
Qualitative and aqueous dispersion.Compared to using noble metal (such as gold, silver) realization antibacterial applications, using carbon material have into
This cheap advantage.However, realize the mainly graphene of antibacterial applications currently with carbon material, its preparation process is complicated, into
This height, water dispersible are poor and antibacterial effect is bad.The present invention prepares the carbon with excellent antibacterial property using one-step method hydro-thermal and received
Rice ball, preparation method is extremely simple, cost is cheap, can be mass-produced, and water dispersible is good, biocompatibility is good, tool
There are the great potentials such as antibacterial applications in organism, daily life antibacterial applications.
The present invention is using band amino macromolecule and alkyl betaine as raw material, and using hydro-thermal method, a step has been made and had first
The quaternization Nano carbon balls of excellent antibacterial performance.Transmission electron microscope figure shows the Nano carbon balls even size distribution, put down
Equal size in 100nm or so and has good dispersiveness.Cytotoxin experiment shows that the Nano carbon balls are to golden yellow grape
Coccus has good restraining and sterilizing bacteria performance.The carbon, which is received, to be shown to the cell survival rate result of normal liver cell (L02 cells)
Rice ball has relatively low cytotoxicity, is expected at biomedicine field, daily chemical product, purifying water process and various antibacterial interfaces
It is used widely Deng field.
The content of the invention
The technical problem to be solved in the present invention is to provide a kind of water soluble quaternary ammonium salinization Nano carbon balls, to solve prior art
The problems such as existing preparation process is complicated, and cost is higher and antibacterial effect is bad.
The present invention also technical problems to be solved are to provide the preparation method of above-mentioned water soluble quaternary ammonium salinization Nano carbon balls.
Last technical problems to be solved of the invention are to provide the application of above-mentioned water soluble quaternary ammonium salinization Nano carbon balls.
In order to solve the above technical problems, the technical solution adopted by the present invention is as follows：
A kind of water soluble quaternary ammonium salinization Nano carbon balls, it includes the Nano carbon balls being mainly made up of carbon and grafting
Alkyl betaine on Nano carbon balls surface.
Wherein, described alkyl betaine be empgen BB, myristyl betaine, cetyl betaine and
Any one or a few combination in octadecyl betaine, preferably cetyl betaine；The structural formula of alkyl betaine
It is as follows：
The preparation method of above-mentioned water soluble quaternary ammonium salinization Nano carbon balls, it comprises the following steps：
(1) after the high-molecular compound with amino being dissolved in into water, alkyl betaine is added, it is standby after being well mixed；
(2) mixed system of gained in step (1) is reacted 12~36 hours at 160~200 DEG C, after the completion of reaction
To Nano carbon balls solution and dialysed, produce water soluble quaternary ammonium salinization Nano carbon balls.
In step (1), the high-molecular compound with amino is chitosan, polyethyleneimine, polypropylene amine, ox blood
Pure albumen or lysozyme.
In step (1), for the water-soluble bad high-molecular compound with amino, can by added into water hydrochloric acid or
The mode of acetic acid, the high-molecular compound with amino is set to be dissolved completely in water.
In step (1), the mass ratio of alkyl betaine and high-molecular compound is 1：5~50.
Wherein, described alkyl betaine is preferably cetyl betaine, the high-molecular compound with amino
The mass ratio of preferably chitosan, cetyl betaine and chitosan is 1：10；When cetyl betaine is replaced by it
During its alkyl betaine, other alkyl betaines are identical with the amount of the material of cetyl betaine.
In step (2), in the dialysis operation, dialyzate is deionized water, and the specification of dialysis membrane (or bag filter) is point
Son amount is 1000.
In step (2), the dialysis operation can be replaced by centrifugally operated；Wherein, centrifugal rotational speed be 1000~30000 turns/
Minute, centrifugation time is 1~120 minute.
Application of the above-mentioned water soluble quaternary ammonium salinization Nano carbon balls in terms of as antibacterial agent is also in the protection model of the present invention
Within enclosing.
Application of the above-mentioned water soluble quaternary ammonium salinization Nano carbon balls in antibacterials are prepared is also in protection scope of the present invention
Within.
Wherein, above-mentioned water soluble quaternary ammonium salinization Nano carbon balls can suppress and kill gram-positive bacteria.
Beneficial effect：The present invention completes the grafting of high-molecular compound and alkyl betaine, system using the step of hydro-thermal method one
The Nano carbon balls obtained have good water-soluble and excellent broad spectrum antibacterial performance, compared with prior art, have following advantage：
(1) preparation of the Nano carbon balls with anti-microbial property is completed using the step of hydro-thermal method one, preparation method is simple, raw material
It is inexpensive, can largely prepare.
(2) excellent anti-microbial property：There is good antibacterial and bactericidal effect to gram-positive bacteria bacterium；1 × 105~
1×106Under CFU/mL bacterium numbers, the MIC of staphylococcus aureus is 4 μ g/mL；The MIC of bacillus subtilis is 5 μ g/mL；
The MIC of micrococcus luteus is 2 μ g/mL.
(3) cytotoxicity is low：Show normal liver cell MTT results also more than 80% survival under 30 μ g/mL
Rate, it may be applied in terms of antibacterial agent in vivo.
(4) Nano carbon balls produced by the present invention have good water dispersible and stability, are adapted in aqueous organism
Various antibacterial applications in system.
Brief description of the drawings
Fig. 1 is that water-soluble quaternization Nano carbon balls prepare schematic diagram in embodiment 1；
Fig. 2 is the SEM (SEM) for the water soluble quaternary ammonium salinization Nano carbon balls being prepared in embodiment 1
Figure；
Results of the Fig. 3 for water-soluble quaternization Nano carbon balls in embodiment 8 to the bacteriostatic experiment of staphylococcus aureus
Schematic diagram；
Fig. 4 is that the middle plateform of embodiment 9 is coated with experimental result schematic diagram；
Fig. 5 is that water-soluble quaternization Nano carbon balls are tested to the toxicity detection of normal liver cell (L02) in embodiment 13
Result schematic diagram.
Embodiment
Further explanation is made to the present invention below in conjunction with the accompanying drawings
Embodiment 1
The preparation (see Fig. 1) of water soluble quaternary ammonium salinization Nano carbon balls, comprises the following steps：
(1) chitosan is dissolved in aqueous hydrochloric acid solution；
(2) cetyl betaine is added in chitosan solution, heating for dissolving stirs and evenly mixs；
(3) mixed system of gained in step (2) is reacted 20 hours at 180 DEG C, forms Nano carbon balls solution；
(4) the above-mentioned Nano carbon balls solution of dialysis purification is passed through.
Wherein,
The mass ratio of the cetyl betaine and chitosan is 1：10；
Dialyzate is deionized water, and the molecular weight of dialysis membrane is 1000；
Obtained Nano carbon balls particle diameter is 100nm or so (see Fig. 2).
Embodiment 2
Preparation method is same as Example 1, except that, in step (3), the reaction time is 24 hours, reaction temperature
For 160 DEG C.
Embodiment 3
Preparation method is same as Example 1, except that, in step (3), the reaction time is 12 hours, reaction temperature
For 200 DEG C.
Embodiment 4
Preparation method is same as Example 1, except that, the chitosan in step (1) is replaced with into polyethylene respectively
Imines, polypropylene amine, bovine serum albumin(BSA) and lysozyme, amount used is as the quality of chitosan.4 kinds of differences are prepared
Water soluble quaternary ammonium salinization Nano carbon balls.
Embodiment 5
Preparation method is same as Example 1, except that, the mass ratio of cetyl betaine and chitosan is distinguished
Replace with 1：5 and 1：50,2 kinds of different water soluble quaternary ammonium salinization Nano carbon balls are prepared.
Embodiment 6
Preparation method is same as Example 1, except that, cetyl betaine is replaced with to dodecyl sweet tea respectively
Dish alkali, myristyl betaine and octadecyl betaine, 3 kinds of different water soluble quaternary ammonium salinization Nano carbon balls are prepared.
Embodiment 7
Preparation method is same as Example 1, except that, aqueous hydrochloric acid solution is replaced with to aqueous acetic acid, nitre respectively
Aqueous acid and aqueous sulfuric acid, 3 kinds of different water soluble quaternary ammonium salinization Nano carbon balls are prepared.
Embodiment 8
The water soluble quaternary ammonium salinization Nano carbon balls of testing example 1 are to the bacteriostasis of staphylococcus aureus, and method is such as
Under：
The staphylococcus aureus of overnight incubation is chosen, with 1:30 dilution proportion, 2~3 are grown in 37 DEG C of incubators
Absorbance of the individual hour to bacterium at 600nm is 0.5 or so, and now the number of bacterium is about 1 × 108CFU/mL.Will be golden yellow
Color staphylococcus is with the culture medium containing various concentrations Nano carbon balls (0,5,10,20,30,40 μ g/mL) with 1:10 ratio is dilute
After releasing, after being placed in 37 DEG C of cultures 24 hours, the absorbance at 600nm is determined, experimental result is shown in Fig. 3.Test result indicates that
Bacterium number is 1 × 106~1 × 107In the case of CFU/mL, when Nano carbon balls concentration is 10 μ g/mL, you can kill most of gold
Staphylococcus aureus simultaneously realize long-term suppress.
Embodiment 9
The Nano carbon balls of spread plate testing example 1 are as follows to the bacteriostasis of staphylococcus aureus, method：
The staphylococcus aureus of overnight incubation is chosen, with 1:30 dilution proportion, 2~3 are grown in 37 DEG C of incubators
Absorbance of the individual hour to bacterium at 600nm is 0.5 or so.By staphylococcus aureus and contain various concentrations Nano carbon balls
The culture medium of (0,5 μ g/mL) is with 1:10 dilution proportion, be placed in 37 DEG C culture 2 hours after, respectively by bacterium solution in physiological saline
Stepwise dilution, final 10000 times of dilution, and take the μ L of dilution 100 to be placed on the culture medium flat plate solidified, then it is fast with spreading rod
Fastly by its even spread, after being placed in 37 DEG C of 14~18 hours of culture, counting of taking pictures is carried out to it, experimental result is shown in Fig. 4, its
Clump count is 1137 in middle control, and clump count is 1 in 5 μ g/mL Nano carbon balls.Flat board be coated with test result indicates that, in bacterium
Number is 1 × 106~1 × 107In the case of CFU/mL, when Nano carbon balls concentration is 5 μ g/mL, you can it is golden yellow to kill the overwhelming majority
Staphylococcus.
Embodiment 10
The Nano carbon balls of testing example 1 are as follows to the MIC of staphylococcus aureus measure, method：
The staphylococcus aureus of overnight incubation is chosen, with 1:30 dilution proportion, 2~3 are grown in 37 DEG C of incubators
Absorbance of the individual hour to bacterium at 600nm is 0.5 or so.By staphylococcus aureus and the carbon nanometer containing various concentrations
The culture medium of ball (0,1,2,3,4,5,6 μ g/mL) is with 1:After 100 dilution proportion, 37 DEG C of 14~18 hours of culture are placed in
Afterwards, there is not the concentration of obvious muddiness, as MIC of the Nano carbon balls to staphylococcus aureus.Test result indicates that in gold
The number of staphylococcus aureus is 1 × 105~1 × 106During CFU/mL, when the Nano carbon balls concentration is 4 μ g/mL, do not occur muddy
Turbid, 4 μ g/mL are the MIC to staphylococcus aureus.
Embodiment 11
Nano carbon balls are similar to Example 10 to the MIC of bacillus subtilis measure, test result indicates that, in withered grass
The number of bacillus is 1 × 105~1 × 106During CFU/mL, when the Nano carbon balls concentration is 5 μ g/mL, there is not muddiness, 5
μ g/mL are the MIC to bacillus subtilis.
Embodiment 12
Nano carbon balls are similar to Example 10 to the MIC of micrococcus luteus measure, test result indicates that, it is micro- in gamboge
The number of coccus is 1 × 105~1 × 106During CFU/mL, when the Nano carbon balls concentration is 2 μ g/mL, there are not muddiness, 2 μ g/
ML is the MIC to micrococcus luteus.
Embodiment 13
The cytotoxicity of the Nano carbon balls of testing example 1, method are as follows：
Normal liver cell L02 is selected, with 5 × 104Individual/mL cells are respectively 0,2,5,10,20,30 μ g/mL's with concentration
After Nano carbon balls are incubated 24 hours, the toxicity using ELIASA using MTT detection methods measure Nano carbon balls to L02 cells, as a result
See Fig. 5.Test result indicates that Nano carbon balls concentration is in the case where being far longer than bacterium MIC concentration, cell still has more than 80% to deposit
Motility rate, illustrate that the Nano carbon balls have good biocompatibility.
Claims (9)
1. a kind of water soluble quaternary ammonium salinization Nano carbon balls, it is characterised in that it includes a Nano carbon balls and is grafted on carbon nanometer
The alkyl betaine of ball surface.
2. water soluble quaternary ammonium salinization Nano carbon balls according to claim 1, it is characterised in that described alkyl betaine is
In empgen BB, myristyl betaine, cetyl betaine and octadecyl betaine any one or it is several
The combination of kind.
3. the preparation method of the water soluble quaternary ammonium salinization Nano carbon balls described in claim 1, it is characterised in that it includes following step
Suddenly：
(1) after the high-molecular compound with amino being dissolved in into water, alkyl betaine is added, it is standby after being well mixed；
(2) mixed system of gained in step (1) is reacted 12~36 hours at 160~200 DEG C, carbon is obtained after the completion of reaction
Nanosphere solution is simultaneously dialysed, and produces water soluble quaternary ammonium salinization Nano carbon balls.
4. preparation method according to claim 3, it is characterised in that the high-molecular compound with amino gathers for shell
Sugar, polyethyleneimine, polypropylene amine, bovine serum albumin(BSA) or lysozyme.
5. preparation method according to claim 3, it is characterised in that in step (1), alkyl betaine and macromolecule chemical combination
The mass ratio of thing is 1:5~1:50.
6. preparation method according to claim 3, it is characterised in that in step (2), in the dialysis operation, dialyzate
For deionized water, the molecular weight of dialysis membrane is 1000.
7. preparation method according to claim 3, it is characterised in that in step (2), described dialysis operation is grasped by centrifugation
Replace；Wherein, centrifugal rotational speed is 1000~30000 revs/min, and centrifugation time is 1~120 minute.
8. application of the water soluble quaternary ammonium salinization Nano carbon balls in terms of as antibacterial agent described in claim 1.
9. application of the water soluble quaternary ammonium salinization Nano carbon balls in antibacterials are prepared described in claim 1.
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| SG10201809275WA (en) | 2017-10-19 | 2019-05-30 | Agency Science Tech & Res | Hybrid Nanodots for Bacteria Staining and Antimicrobial Applications |
| CN108300464B (en) * | 2018-04-17 | 2021-03-30 | 南京师范大学 | Preparation method of antibacterial N-doped carbon quantum dot, product and application thereof |
| CN108854599B (en) * | 2018-05-14 | 2020-10-16 | 陕西师范大学 | Dialysis membrane based on cross-linked lysozyme and application thereof |
| CN111763329A (en) * | 2020-05-25 | 2020-10-13 | 上海麟定生物科技有限公司 | Quaternized polyethyleneimine modified graphene quantum dot, and preparation method and application thereof |
| CN112521942B (en) * | 2020-11-19 | 2022-03-29 | 华南理工大学 | Functionalized carbon quantum dot and preparation method thereof |
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