CN107711828A - Silver/cation copolymer modified Nano diamond compound particle and preparation method thereof - Google Patents
Silver/cation copolymer modified Nano diamond compound particle and preparation method thereof Download PDFInfo
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- CN107711828A CN107711828A CN201710832560.7A CN201710832560A CN107711828A CN 107711828 A CN107711828 A CN 107711828A CN 201710832560 A CN201710832560 A CN 201710832560A CN 107711828 A CN107711828 A CN 107711828A
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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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N59/16—Heavy metals; Compounds thereof
Abstract
The invention discloses a kind of silver/cation copolymer modified Nano diamond compound particle and preparation method thereof, the compound particle is by the way that copolymer is modified to the Nano diamond of alkylation, nano-silver loaded is obtained on its surface again, wherein, copolymer is using 4 vinylpyridines and the product after hydroxyethyl methacrylate copolymerization.Gained antiseptic has to gramnegative bacterium Escherichia coli and gram-positive bacterium staphylococcus aureus preferably suppresses killing action, corresponding minimal inhibitory concentration is respectively 50 μ g/mL and 25 μ g/mL, and inhibition zone is obvious, to Escherichia coli 90min sterilization rates up to 100%；Antiseptic prepared by the present invention can be added in some medical composite materials as additive, for fields such as plastic surgery, bone engagement and/or interior prostheses, particularly it is used in the case of having high risk of infection, its excellent anti-microbial property is assigned while its mechanical performance is strengthened, extend medicine equipment service life, reduce patient's infection risk.
Description
Technical field
The invention belongs to antiseptic to synthesize field, is related to a kind of medical composite material, and in particular to a kind of silver/cation is common
Polymerized Nano diamond compound particle and preparation method thereof.
Background technology
How effectively to prevent and treat post-operative infection all to receive much concern all the time, treatment bacterium infection tradition side
Method is by injection or oral antibiotic.But as drug-fast bacteria occurs, conventional antibiotic therapy cure rate reduces year by year.Closely
Nian Lai, nano antibacterial agent are widely studied by researcher as a kind of new way for treating drug-fast bacteria infection.Jang etc.
People（Non-patent literature）It is prepared for the Nano particles of silicon dioxide of small molecule quaternary ammonium salt modification so that the antimicrobial efficiency of quaternary ammonium salt is big
Width improves, and its anti-microbial property gradually increases with the reduction of silica particle diameter.
Nano diamond（ND）As a kind of new carbon-based material, be widely used in the past few decades polishing,
The fields such as superhard coating, imaging and drug delivery.Due to its good stability, excellent biocompatibility and minimum grain
Footpath can make the good carrier of antiseptic.The cationic homopolymer of the poly- tetravinyl pyridiniujm of CN105253882A patent documents
Easy functional modification is carried out to ND, not only solves the serious agglomeration traits of ND, while assign ND excellent antibacterials
Performance, for ND, in antibacterial field, application opens a new road.CN104987052A patent documents are by nanometer Buddha's warrior attendant
Stone and antiseptic are mixed to join in ceramics, obtain mechanical strength enhancing, and the ceramics with anti-microbial property.
CN105802046A patent documents enhance the anti-wear performance of rubber slab, and add using the addition of the raw materials such as Nano diamond
Enter N-（Trichloromethyl sulphur）Phthalimide, BIT, make rubber have antibacterial and antimildew function.
Nano silver grain is as a kind of important inorganic nano antiseptic, has a broad antifungal spectrum, sterilization of high efficiency, to mammalian cell toxicity
It is low and be not easy to cause microorganism drug resistance.CN1241662A patent documents adhere between the fiber of fabric or on fiber
Particle diameter is 1~100 nanometer of ultra micron silver（Ag）, the superficial layer of ultra micron silver is silver oxide, and core is argent, by discharging Ag+Reach sterilization efficacy.The Ag-TiO of CN102497892A patent documents invention2Coating is used for numerous existing medical instruments
In implant.
Existing research is mixed by Nano diamond with the simple physical of antiseptic is used as nano anti-biotic material, wherein, and
The Nano diamond that mixing adds unprocessed directly limits its enhancing and increased because particle diameter is excessive, particle size distribution range is too wide
Tough ability.On the other hand, Ag is deposited directly on the porous materials such as fabric, dressing more, and the Ag nano particles so obtained are difficult
Exempt from the problem for being easy to come off be present, and nano silver antimicrobials are to the antibacterial ability relative deficiency of gram-positive bacterium.
The content of the invention
The purpose of the present invention, for biologic medical industry, increases to provide a kind of high-efficiency compound antibacterial agent and preparation method thereof
Strong medicine equipment service life simultaneously assigns its antibacterial characteristics.
Realizing the technical solution of the object of the invention is：
Silver of the present invention/cation copolymer modified Nano diamond compound particle, by by copolymer to alkylation
Nano diamond is modified, then nano-silver loaded is obtained on its surface.
Further, copolymer is using 4-vinylpridine and the product after hydroxyethyl methacrylate copolymerization.
Further, the Nano diamond of alkylation by by Nano diamond and bromopropyl trimethoxy silane in alcohol water
Obtained after being reacted in solution.
Further, described modification is to react copolymer in ethanol with the Nano diamond being alkylated, and is used
Excessive bromohexane make copolymer fully it is quaternized after obtain.
Further, the load capacity of Nano Silver is controlled 50 ~ 60%.
The method of the preparation of above-mentioned compound particle, comprises the following steps：
Step 1, copolymer（PVP-co-HEMA）Preparation：Azodiisobutyronitrile（AIBN）As thermal initiator, by 4- vinyl
Pyridine stirs with hydroxyethyl methacrylate Hybrid Heating, purifying, vacuum drying；
Step 2, Nano diamond reacts with bromopropyl trimethoxy silane in alcohol solution, product（BrND）Centrifugation, washing,
Dry；
Step 3, step 2 products therefrom reacts in ethanol with copolymer described in step 1, and adds excessive bromohexane and make copolymer
Abundant quaternized, product（QND）Centrifugation, washing, dry；
Step 4, step 3 products therefrom is dispersed in distilled water, with AgNO3The aqueous solution is mixed and boiled, and adds reducing agent lemon
Lemon acid sodium, boils jointly, centrifuges, washs, is dried in vacuo.
In a preferred embodiment, in step 1, the mol ratio of 4-vinylpridine and hydroxyethyl methacrylate
For 100：（1~100）, reaction temperature is 60 DEG C, reaction time 24h.
In a preferred embodiment, in step 2, ethanol, water volume ratio 9 in alcohol solution：1, in a small amount of water
Under conditions of, silane coupler can hydrolyze；The mass ratio of Nano diamond and alcohol solution（1~5 ：100）, nanogold
Hard rock mass fraction in alcohol solution is excessive or too small is all unfavorable for its abundant reaction with silane coupler.
In a preferred embodiment, in step 3, step 2 products therefrom BrND and copolymer p VP- described in step 1
Co-HEMA in mass ratio 100：（50~300）, reaction temperature 50 ~ 80oC, 10 ~ 24h of time.
In a preferred embodiment, in step 4, Nano diamond, silver nitrate, sodium citrate in step 2
Mass ratio is 1：（1-1.5）：（1-2）.
Nano diamond provided by the invention is used for composite, biologic medical field, is particularly used for having high infection danger
In the case of danger.
Compared with prior art, its remarkable advantage is the present invention：
1. the polymer antibacterial agent of cation copolymer is incorporated on ND carriers by the present invention, high score not only can be effectively avoided
The loss of son and the pollution to environment, and can reuse.
2. the Nano diamond size of cation copolymer modification is small, the characteristics of specific surface area is big can provide more with
Bacterium contacts target spot, can greatly improve the antibacterial ability of polymer antibacterial agent, increases antimicrobial efficiency.
3. macromolecule is as activated centre, in-situ preparation Nano silver grain, and by the coordination with Nano silver grain,
Make the silver nanoparticle particle diameter of preparation relatively stable.
4. the antiseptic that the present invention obtains is contact-type and release type complex antimicrobials, antibacterial effect is quickly excellent, to big
Enterobacteria 90min sterilization rates are up to 100%.
5. Nano diamond quality is hard, wearability is good, and material will likely be greatly improved by being added in the materials such as resin
Mechanical performance.
6. antiseptic prepared by the present invention can be added in some medical composite materials as additive, for plastic surgery,
The field such as bone engagement and/or interior prosthese, particularly it is used in the case of having high risk of infection, while its mechanical performance is strengthened
Its excellent anti-microbial property is assigned, extends medicine equipment service life, reduces patient's infection risk.
Brief description of the drawings
Fig. 1 is in the embodiment of the present invention 1（a）Raw material ND,（b）QND、（c）QND@Ag infrared spectrums.
Fig. 2 is raw material in the embodiment of the present invention 1（a）ND、（b）QND、（c）QND@Ag XRD.
Fig. 3 is in the embodiment of the present invention 1（a）Raw material ND,（b）QND,（C, d）QND@Ag amplify transmission electron microscope picture.
Fig. 4 is the hydration grain size distribution of raw material ND, BrND, QND, QND Ag in the embodiment of the present invention 1.
Fig. 5 is Bactericidal test result figure in the embodiment of the present invention 1（a）E. coli,（b）S. aureus:（1）Blank pair
According to,（2）Raw material ND,（3）QND,（4）QND @Ag.
Fig. 6 is the antibacterial kinetic curve of the embodiment of the present invention 1.
Embodiment
The preparation method of silver/cation copolymer modified Nano diamond compound particle, comprises the following steps：
It is prepared by a.PVP-co-HEMA：Azodiisobutyronitrile AIBN is as thermal initiator, by 4-vinylpridine and methacrylic acid
Hydroxyl ethyl ester Hybrid Heating stirs, and gained mixture precipitates three times in hexane, vacuum drying.
B.ND reacts with bromopropyl trimethoxy silane in alcohol solution, product（BrND）Centrifugation, wash, dry.
C.BrND and PVP-co-HEMA reacts in ethanol, and adds excessive bromohexane and make the abundant quaternary ammoniums of PVP-co-HEMA
Change, product（QND）Centrifugation, washing, dry, add excessive bromohexane, quaternization degree is improved, ND dispersiveness and sun from
The anti-microbial property of sub- polymer all gets a promotion.
D. QND obtained above is dispersed in distilled water, with AgNO3The aqueous solution is mixed and boiled, and adds sodium citrate,
Boil jointly, centrifuge, wash, be dried in vacuo, organic polymer makes the silver of preparation by the coordination with Nano silver grain
Nanometer particle size more stable homogeneous, silver nano-grain particle diameter is obtained in 20-50nm.
Embodiment 1
Step a:Azodiisobutyronitrile AIBN passes through radical polymerization synthetic copolymer as thermal initiator.4- vinylpyridines
The mol ratio 70/30 of pyridine monomer and hydroxyethyl methacrylate.Mixture is stirred in 60 DEG C of oil bath and to heat 24 small
When.Finally, reactant mixture is precipitated three times in hexane, and dried in vacuum drying oven, obtain faint yellow product.
Step b:Weigh raw material ND100mg and be added to 20mL alcohol solutions（VEthanol：VWater=9:1）, then ND mass is pressed thereto
10%（10mg）Add silane coupler（Bromopropyl trimethoxy silane）, magnetic agitation 24h at 50 DEG C, product centrifugation, spend
Ion water washing three times, is put into 60 DEG C of dryings of vacuum drying chamber.
Step c:50mgBrND is dissolved in 20ml ethanol solutions, adds 50mg copolymer ps VP-co-HEMA, at 70 DEG C
24h is reacted, adds excessive bromohexane（0.12g）Make it fully quaternized, product centrifugation, washed 3 times with ethanol, 50 DEG C true
Sky dries 12h and obtains quaternised modified Nano diamond（QND）.
Step d:50mg QND obtained above are taken to be dispersed in 20 mL distilled water, with 100 mL AgNO3（60mg）Water
Solution is mixed and boiled, and adds 68 mg sodium citrates（Mass ratio, Nano diamond：Silver nitrate：Sodium citrate=1：1.2：
1.4）, keep 1 h of solution boiling.Centrifuge, deionization washing is dried in vacuo 24h after 60 DEG C three times, obtains QND Ag.
Obtained QND@Ag are characterized by infrared, XRD, TEM, DLS and contrasted with raw material ND, QND etc..
It will be noted from fig. 1 that compared to ND original powder, QND and QND@Ag infrared spectrum peak number increases, wherein 2880-
2970 cm-1For-CH3、-CH2Stretching vibration peak, 1601 cm-1With 1569 cm-1It is C=N stretching vibration peak, 1515 Hes
1466 cm-1It is C=C stretching vibration peak, 1714 cm-1For C=O stretching vibration peaks, 1045cm-1Symmetrical corresponding to C-O-C stretches
Contracting vibration peak.Further, since 1640 cm-1There is C=N in place+Peak, illustrate that Nano diamond surface is successfully introduced into cation and gathered
Compound.In addition, the contrast of QND@Ag and QND infrared spectrums is found out：Due to Ag NPs and hydroxyl, the pyridine radicals of ND surface polymers
Group forms coordinate bond, and its infrared spectrum is in 3400 cm-1, 1601 cm-1With 1569 cm-1Place all substantially weakens at peak, so as to prove
Interaction between the polymer of nanometer Ag and ND surface graftings be present, and the effect can keep the Ag NPs of ND area loads
It is stable.
43 in Fig. 2o、75oIt is the characteristic diffraction peak of Nano diamond, corresponds to Nano diamond respectively（1 1 1）With（2 2
0）Cubic crystal face.The crystalline form of Nano diamond is had not significant impact after graft polymers, but due to the parcel of organic matter,
The remitted its fury of Nano diamond diffraction maximum, prove that Nano diamond is successfully modified from other side.Because silver has strongly
Crystallization tendency, its peak covers the diffraction maximum of Nano diamond, in QND@Ag XRD diffraction spectrograms, respectively at 38o、44o、
64o、77oPosition occurs Ag's（1 1 1）、（2 0 0）、（2 2 0）、（3 1 1）Four crystal face characteristic diffraction peaks, so as to prove
Silver nanoparticle is successfully loaded on ND surfaces.
It can be seen in figure 3 that raw material ND aggregated particle size reaches micron order, cation copolymer carries out function to its surface
After changing modification, particle diameter is decreased to 10 ~ 100nm, and de-agglomerated effect is fairly obvious.This is due to the ND surfaces of functionalization with a large amount of
Positive charge, interparticle repulsive force is significantly increased, and plays de-agglomerated effect, and the repulsion hinders nano-particle and reunited again.
Figure（c）、（d）Show that QND has successfully loaded Ag nano particles, this is consistent with XRD result, institute's loaded Ag nano particle diameter compared with
To be homogeneous, about in 10 ~ 100 nm, and the composite nanoparticle carried after silver still keeps preferable particle dispersive property.Fig. 4 is hydrated
Grain size distribution is consistent with tem observation result, and modified Nano diamond has stable dispersiveness.
In terms of anti-microbial property, the complex antimicrobials have obvious antibacterial to Escherichia coli and staphylococcus aureus
Circle, such as Fig. 5.Antibacterial kinetic test show QND@Ag to Escherichia coli 90min sterilizing rates up to 100%, such as Fig. 6.In addition, test
The complex antimicrobials are 10 to bacterium colony concentration6CFU/mL Escherichia coli and staphylococcus aureus antibacterial activity, are obtained most
Small Mlc（MIC）Respectively 50 μ g/mL and 25 μ g/mL, there is good anti-microbial property.
Embodiment 2 ~ 4 gives different monomers mol ratio 4-vinylpridine and methyl-prop according to the experimental method of embodiment 1
Olefin(e) acid hydroxyl ethyl ester, different silver nitrate concentrations, in the case of different sodium citrate amounts, the different composite anti-biotic material of acquisition.
Antiseptic prepared by the present invention can be added in some medical composite materials as additive, for plastic surgery, bone
The field such as engagement and/or interior prosthese, particularly it is used in the case of having high risk of infection, is assigned while its mechanical performance is strengthened
Its excellent anti-microbial property is given, extends medicine equipment service life, reduces patient's infection risk.
Embodiment 2
Step a:The mol ratio 95/5 of 4-vinylpridine monomer and hydroxyethyl methacrylate.
Step d:Mass ratio, Nano diamond：Silver nitrate：Sodium citrate=1：1.2：1.4, keep 1 h of solution boiling.
Embodiment 3
Step a:The mol ratio 90/10 of 4-vinylpridine monomer and hydroxyethyl methacrylate.
Step d:Mass ratio, Nano diamond：Silver nitrate：Sodium citrate=1：1.2：1.4, keep 1 h of solution boiling.
Embodiment 4
Step a:The mol ratio 50/50 of 4-vinylpridine monomer and hydroxyethyl methacrylate.
Step d:Mass ratio, Nano diamond：Silver nitrate：Sodium citrate=1：1.2：1.4, keep 1 h of solution boiling.
Embodiment 5
Step a:The mol ratio 70/30 of 4-vinylpridine monomer and hydroxyethyl methacrylate.
Step d:Mass ratio, Nano diamond：Silver nitrate：Sodium citrate=1：1：1, keep 1 h of solution boiling.
Embodiment 6
Step a:The mol ratio 70/30 of 4-vinylpridine monomer and hydroxyethyl methacrylate.
Step d:Mass ratio, Nano diamond：Silver nitrate：Sodium citrate=1：1：2, keep 1 h of solution boiling.
Embodiment 7
Step a:The mol ratio 70/30 of 4-vinylpridine monomer and hydroxyethyl methacrylate.
Step d:Mass ratio, Nano diamond：Silver nitrate：Sodium citrate=1：1.5：1, keep 1 h of solution boiling.
Embodiment 8
Step a:The mol ratio 70/30 of 4-vinylpridine monomer and hydroxyethyl methacrylate.
Step d:Mass ratio, Nano diamond：Silver nitrate：Sodium citrate=1：1.5：2, keep 1 h of solution boiling.
Embodiment 9
Step a:The mol ratio 70/30 of 4-vinylpridine monomer and hydroxyethyl methacrylate.
Step d:Mass ratio, Nano diamond：Silver nitrate：Sodium citrate=1：1.2：1.4, keep 0.5 h of solution boiling.
Embodiment 10
Step a:The mol ratio 70/30 of 4-vinylpridine monomer and hydroxyethyl methacrylate.
Step d:Mass ratio, Nano diamond：Silver nitrate：Sodium citrate=1：1.2：1.4, keep 1.5 h of solution boiling.
Embodiment 11
Step a:The mol ratio 70/30 of 4-vinylpridine monomer and hydroxyethyl methacrylate.
Step d:Mass ratio, Nano diamond：Silver nitrate：Sodium citrate=1：1.2：1.4, keep 2 h of solution boiling.
After tested, table 1 lists composite antibacterial material that embodiment 1 ~ 4 provides respectively to Escherichia coli（E. coli）And gold
Staphylococcus aureus（S. aureus）Minimal inhibitory concentration（MIC）And inhibition zone size.
Claims (10)
1. silver medal/cation copolymer modified Nano diamond compound particle, it is characterised in that by by copolymer to alkylation
Nano diamond is modified, then nano-silver loaded is obtained on its surface, wherein, copolymer uses 4-vinylpridine and first
Product after the copolymerization of base hydroxy-ethyl acrylate.
2. compound particle as claimed in claim 1, it is characterised in that the Nano diamond of alkylation is by by Nano diamond
Obtained after being reacted with bromopropyl trimethoxy silane in alcohol solution.
3. compound particle as claimed in claim 1, it is characterised in that described modification is the nanometer by copolymer and alkylation
Diamond reacts in ethanol, and using excessive bromohexane make copolymer fully it is quaternized after obtain.
4. compound particle as claimed in claim 1, it is characterised in that the load capacity of Nano Silver is controlled 50 ~ 60%.
5. the preparation method of the compound particle as described in claim 1-4 is any, it is characterised in that comprise the following steps：
Step 1, the preparation of copolymer：Azodiisobutyronitrile is as thermal initiator, by 4-vinylpridine and hydroxyethyl methacrylate
Ethyl ester Hybrid Heating stirs, purifying, vacuum drying；
Step 2, Nano diamond reacts with bromopropyl trimethoxy silane in alcohol solution, product centrifugation, washs, dries；
Step 3, step 2 products therefrom reacts in ethanol with copolymer described in step 1, and adds excessive bromohexane and make copolymer
It is fully quaternized, product centrifugation, washing, dry；
Step 4, step 3 products therefrom is dispersed in distilled water, with AgNO3The aqueous solution is mixed and boiled, and adds reducing agent lemon
Sour sodium, boils jointly, centrifuges, washs, is dried in vacuo.
6. preparation method as claimed in claim 5, it is characterised in that in step 1,4-vinylpridine and hydroxyethyl methacrylate
The mol ratio of ethyl ester is 100：1 ~ 100, reaction temperature is 60 DEG C, reaction time 24h.
7. preparation method as claimed in claim 5, it is characterised in that in step 2, ethanol, water volume ratio in alcohol solution
9：1；The mass ratio 1 ~ 5 of Nano diamond and alcohol solution：100.
8. preparation method as claimed in claim 5, it is characterised in that in step 3, described in step 2 products therefrom and step 1 altogether
Polymers in mass ratio 100：50 ~ 300 react in ethanol, reaction temperature 50 ~ 80oC, 10 ~ 24h of time.
9. preparation method as claimed in claim 5, it is characterised in that in step 4, Nano diamond, nitre described in step 2
Sour silver, the mass ratio of sodium citrate are 1：1-1.5：1-2.
10. antiseptic prepared by the compound particle as described in claim 1-4 is any.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111328831A (en) * | 2020-03-06 | 2020-06-26 | 康特善利(上海)生物科技有限公司 | Antibacterial and antivirus material and application thereof |
| CN112062978A (en) * | 2020-08-25 | 2020-12-11 | 广州大学 | Antibacterial microspheres and preparation method thereof |
| WO2022151075A1 (en) * | 2021-01-13 | 2022-07-21 | Diamondtrap Ltd Oy | Active filter layers, filter constructs and methods for improving a filter's capacity of capturing particles and neutralizing pathogenic particles |
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| CN1380363A (en) * | 2002-05-17 | 2002-11-20 | 中山大学 | Nano diamond particle surface treatment method |
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| CN1380363A (en) * | 2002-05-17 | 2002-11-20 | 中山大学 | Nano diamond particle surface treatment method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111328831A (en) * | 2020-03-06 | 2020-06-26 | 康特善利(上海)生物科技有限公司 | Antibacterial and antivirus material and application thereof |
| CN112841222A (en) * | 2020-03-06 | 2021-05-28 | 康特善利(上海)生物科技有限公司 | Antibacterial and antivirus material and application thereof |
| CN112062978A (en) * | 2020-08-25 | 2020-12-11 | 广州大学 | Antibacterial microspheres and preparation method thereof |
| WO2022151075A1 (en) * | 2021-01-13 | 2022-07-21 | Diamondtrap Ltd Oy | Active filter layers, filter constructs and methods for improving a filter's capacity of capturing particles and neutralizing pathogenic particles |
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