CN108324949A - A kind of hydroxyapatite-carbonitride compound particle and its in-situ composite - Google Patents
A kind of hydroxyapatite-carbonitride compound particle and its in-situ composite Download PDFInfo
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- CN108324949A CN108324949A CN201810233051.7A CN201810233051A CN108324949A CN 108324949 A CN108324949 A CN 108324949A CN 201810233051 A CN201810233051 A CN 201810233051A CN 108324949 A CN108324949 A CN 108324949A
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- hydroxyapatite
- carbonitride
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 32
- 239000002245 particle Substances 0.000 title claims abstract description 22
- 238000011065 in-situ storage Methods 0.000 title claims abstract description 8
- 239000002131 composite material Substances 0.000 title claims description 8
- 229910052588 hydroxylapatite Inorganic materials 0.000 claims abstract description 25
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 claims abstract description 25
- 239000000463 material Substances 0.000 claims abstract description 15
- 239000003814 drug Substances 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 5
- 229940079593 drug Drugs 0.000 claims abstract description 4
- 239000007788 liquid Substances 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- 238000003837 high-temperature calcination Methods 0.000 claims abstract 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 12
- 239000011259 mixed solution Substances 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 6
- VWDWKYIASSYTQR-YTBWXGASSA-N sodium;dioxido(oxo)azanium Chemical compound [Na+].[O-][15N+]([O-])=O VWDWKYIASSYTQR-YTBWXGASSA-N 0.000 claims description 6
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 4
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 238000005245 sintering Methods 0.000 claims description 3
- 229920000877 Melamine resin Polymers 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 claims description 2
- 229910000388 diammonium phosphate Inorganic materials 0.000 claims description 2
- 235000019838 diammonium phosphate Nutrition 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 239000011246 composite particle Substances 0.000 claims 3
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims 2
- 239000002243 precursor Substances 0.000 claims 2
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000004108 freeze drying Methods 0.000 claims 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 5
- 231100000135 cytotoxicity Toxicity 0.000 abstract description 3
- 230000003013 cytotoxicity Effects 0.000 abstract description 3
- 238000011068 loading method Methods 0.000 abstract description 2
- 238000005424 photoluminescence Methods 0.000 abstract description 2
- 210000004027 cell Anatomy 0.000 description 17
- 238000013019 agitation Methods 0.000 description 5
- 229910052761 rare earth metal Inorganic materials 0.000 description 4
- 150000002910 rare earth metals Chemical class 0.000 description 4
- 230000003993 interaction Effects 0.000 description 3
- 239000002105 nanoparticle Substances 0.000 description 3
- 108010043121 Green Fluorescent Proteins Proteins 0.000 description 2
- KJNGJIPPQOFCSK-UHFFFAOYSA-N [H][Sr][H] Chemical compound [H][Sr][H] KJNGJIPPQOFCSK-UHFFFAOYSA-N 0.000 description 2
- 229910052586 apatite Inorganic materials 0.000 description 2
- 238000003501 co-culture Methods 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 2
- 239000000700 radioactive tracer Substances 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- DMGNFLJBACZMRM-UHFFFAOYSA-N O[P] Chemical compound O[P] DMGNFLJBACZMRM-UHFFFAOYSA-N 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000008614 cellular interaction Effects 0.000 description 1
- 230000004700 cellular uptake Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- QWASAGQCQSHFHZ-UHFFFAOYSA-N cyanamide Chemical class NC#N.NC#N QWASAGQCQSHFHZ-UHFFFAOYSA-N 0.000 description 1
- 150000001912 cyanamides Chemical class 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 231100000263 cytotoxicity test Toxicity 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 239000002135 nanosheet Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000002138 osteoinductive effect Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002096 quantum dot Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0013—Luminescence
- A61K49/0017—Fluorescence in vivo
- A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K47/02—Inorganic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0013—Luminescence
- A61K49/0017—Fluorescence in vivo
- A61K49/005—Fluorescence in vivo characterised by the carrier molecule carrying the fluorescent agent
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Nanotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Medical Informatics (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
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Abstract
The present invention utilizes in-situ compositing, the persursor material for making carbonitride to realize that molecular level mixes in liquid conditions with the raw material for preparing of hydroxyapatite, nanometer hydroxyapatite/carbonitride fluorescent particles nano-complex particle is prepared for by way of high-temperature calcination.Compound particle prepared by the present invention combines two kinds of excellent biocompatibilities of material, has extremely low cytotoxicity.The compound of preparation had both remained the high drug loading rate and bioactivity of hydroxyapatite material itself, while the photoluminescence efficiency of compound particle is imparted using the good fluorescence performance of carbonitride, can be as a kind of pharmaceutical carrier with Detectable effects.
Description
Technical field
The invention belongs to biomedical materials fields, and in particular to a kind of hydroxyapatite and carbonitride fluorescence compound particle
And its in-situ composite.
Background technology
Hydroxyapatite is the main inorganic composition of skeleton and tooth, has good biocompatibility, biology living
Property and osteoinductive, are widely used as excellent Artificial bone material and drug carrier material.Nano-grade hydroxy
The pore structure and higher surface energy of apatite are so as to adsorb organic macromolecule material, and porous structure can be played to medicine
The slow releasing function of object.Hydroxyapatite has very strong permeability as nano material, and medicine can be improved when as pharmaceutical carrier
Object penetrates biomembrane, and drug is made to enter cells play drug effect.But hydroxyapatite as single pharmaceutical carrier when cannot be real
The now function of the trace labelling when it is as pharmaceutical carrier in cell and targeting positioning, can not probe into hydroxyapatite and medicine
Interaction between object and cell, the application which limits hydroxyapatites in clinic.For how identifying hydroxyl phosphorus
Tracer problem of the grey stone material in cell, Chinese patent（Patent of invention be " green fluorescent label with high luminous intensity
Terbium/strontium is co-doped with the preparation method of hydroxyapatite nano particle ", publication number：CN201710184077.2）It is middle occurred frequently using having
The rare earth metal Tb of the green fluorescent label of luminous intensity/strontium codope hydroxyapatite nano particle, by rare earth metal to adulterate
Ion enters in hydroxyapatite lattice, assigns the characteristic of hydroxyl apatite fluorescent.But rare earth metal has certain poison
Property, the normal growth of cell can be had an impact after rare earth metal enters cell.Nano-sheet carbonitride（C3N4）It is a kind of total
Yoke fluorescent material has many advantages, such as good biocompatibility, high quantum production rate, nontoxic and stable fluorescence.By studying C3N4
Quantum dot it is found that C3N4Diameter only about several nanometers can enter in cell well, this just be C3N4With hydroxyl
The composite material of apatite composition enters cell and provides fundamental basis.By C3N4After being combined with each other with hydroxyapatite, inspection is utilized
Survey C3N4Fluorescence reflect the interaction of hydroxyapatite and cell, and the two belongs to the life harmless to cytotoxic
Object material can't be to affecting cells.
The present invention prepares hydroxyapatite and carbonitride fluorescence compound particle using in-situ compounding process, prepared by the present invention
Compound particle realizes for the first time utilizes C3N4The fluorescent characteristic of compound carrys out the interaction of tracer hydroxyapatite in the cell,
C3N4The fluorescence that compound has good biocompatibility and stablizes, this material of cellular uptake will not generate cell secondary make
With the fluorescence stablized also achieves the Detectable effects to composite material.
Invention content
The present invention is not have fluorescent characteristic when solving hydroxyapatite as pharmaceutical carrier, can not probe into it between cell
Interaction and improve fluorescent particles and hydroxyapatite it is compound after enter the toxic side effects generated into the cell to cell and ask
Topic is put forward for the first time two kinds of C with good biocompatibility3N4Compound and hydroxyapatite are prepared into compound particle, this hair
Bright technical solution is, is that nitridation carbon raw material passes through original using diammonium hydrogen phosphate and calcium nitrate as hydroxyapatite raw material with cyanamide
The compound technique being combined with co-sintering in position prepares composite nanoparticle.Mainly include the following steps（Following number is quality
Score）：
（1）The calcium nitrate aqueous solution for preparing 50 parts of a concentration of 0.1M-5M, by 0.1-10 parts of cyanamides（Cyanamide, dicyandiamide, trimerization
It is one or more in cyanamide, urea）It is added in above-mentioned solution, stirs to dissolve and is uniformly mixed；
（2）The ammonium dibasic phosphate aqueous solution for preparing 30 parts of a concentration of 0.1M-5M, is slowly added into above-mentioned solution, is stirred
0.5-5 hours.
（3）Under agitation, the moisture in mixed solution is removed by way of heating or being freeze-dried.
（4）The compound of acquisition is put into high temperature furnace and is heated, heating rate is 1-10 DEG C/min.At 350 DEG C -600 DEG C
Under the conditions of keep 1-4 hour, by sintered product grind into powder.
The device have the advantages that：The present invention prepares compound particle using in-situ compositing, makes C3N4Persursor material
It is mixed in liquid conditions with the raw material for preparing of HAp, the other dispersion effect of molecular level can be reached so that two kinds of constituent elements are realized equal
Even compound and good interface cohesion；Compound prepared by the present invention both remained HAp materials itself high drug loading rate and
Bioactivity, while utilizing C3N4Good fluorescence performance impart the photoluminescence efficiency of compound particle, a kind of tool can be used as
There is the pharmaceutical carrier of Detectable effects；Compound particle prepared by the present invention combines two kinds of excellent biocompatibilities of material, has
Extremely low cytotoxicity, cell survival rate is still higher than 90% under the up to concentration of 500ug/ml.Corresponding testing result is shown in explanation
Book attached drawing：The cytotoxicity test of compound particle（Attached drawing 1）；It, can be with after compound particle co-cultures 4 hours with tumour cell MG63
Observe that compound particle is effectively absorbed by cell, it can be seen that the intense fluorescence in compound particle portion in the cell under light excitation
（Attached drawing 3）.
Description of the drawings
The fluorescence photo for the compound particle that Fig. 1 is obtained by embodiment 4.
Fig. 2 is the cytotoxicity experiment of various concentration compound particle.
Fig. 3 compound particles co-culture photo with MG63 cells（a）Bright field image（b）Dark field image（c）Light and shade overlaps picture.
Specific implementation mode
The present invention is described in detail with reference to embodiments, and the present invention is not limited by these manufacture examples.
Embodiment 1
（1）The calcium nitrate aqueous solution for preparing 50 parts of a concentration of 0.1M, 0.1 part of dicyandiamide is added in above-mentioned solution, stirring makes
It dissolves and is uniformly mixed.
（2）The ammonium dibasic phosphate aqueous solution for preparing 30 parts of a concentration of 0.1M, is slowly added into above-mentioned solution, is stirred
0.5 hour.
（3）Under agitation, the moisture in mixed solution is removed by way of heating or being freeze-dried.
（4）The compound of acquisition is put into high temperature furnace and is heated, heating rate is 5 DEG C/min.It is kept under the conditions of 350 DEG C
4 hours, by sintered product grind into powder.
Embodiment 2
（1）The calcium nitrate aqueous solution for preparing 50 parts of a concentration of 5M, 10 parts of melamines are added in above-mentioned solution, and stirring makes it
It dissolves and is uniformly mixed.
（2）The ammonium dibasic phosphate aqueous solution for preparing 30 parts of a concentration of 5M, is slowly added into above-mentioned solution, stirring 5
Hour.
（3）Under agitation, the moisture in mixed solution is removed by way of heating or being freeze-dried.
（4）The compound of acquisition is put into high temperature furnace and is heated, heating rate is 1 DEG C/min.It is kept under the conditions of 600 DEG C
1 hour, by sintered product grind into powder.
Embodiment 3
（1）The calcium nitrate aqueous solution for preparing 50 parts of a concentration of 2.5M, 5 parts of cyanamide cyanamides are added in above-mentioned solution, are stirred
It makes it dissolve and is uniformly mixed.
（2）The ammonium dibasic phosphate aqueous solution for preparing 30 parts of a concentration of 2.5M, is slowly added into above-mentioned solution, is stirred
3 hours.
（3）Under agitation, the moisture in mixed solution is removed by way of heating or being freeze-dried.
（4）The compound of acquisition is put into high temperature furnace and is heated, heating rate is 10 DEG C/min.It is protected under the conditions of 500 DEG C
3 hours are held, by sintered product grind into powder.
Embodiment 4
（1）The calcium nitrate aqueous solution for preparing 50 parts of a concentration of 2.5M, 2.5 parts of dicyandiamides is added in above-mentioned solution, stirring makes
It dissolves and is uniformly mixed.
（2）The ammonium dibasic phosphate aqueous solution for preparing 30 parts of a concentration of 2.5M, is slowly added into above-mentioned solution, is stirred
2.5 hour.
（3）Under agitation, the moisture in mixed solution is removed by way of heating or being freeze-dried.
（4）The compound of acquisition is put into high temperature furnace and is heated, heating rate is 3 DEG C/min.It is kept under the conditions of 500 DEG C
4 hours, by sintered product grind into powder.
Claims (7)
1. a kind of hydroxyapatite/carbonitride fluorescent nanometer composite particle and its in-situ composite, it is characterized in that making carbonitride
Persursor material realize that molecular level mixes in liquid conditions with the raw material for preparing of hydroxyapatite, pass through the side of high-temperature calcination
Nanometer hydroxyapatite/carbonitride fluorescence compound particle and its in-situ composite prepared by formula.
2. the preparation process of hydroxyapatite according to claim 1/carbonitride fluorescent nanometer composite particle includes as follows
Step：
（1）50 parts of calcium nitrate aqueous solutions are prepared, 0.1-10 parts of carbon nitride precursors are added in above-mentioned solution, stirring keeps its molten
It solves and is uniformly mixed；
（2）The ammonium dibasic phosphate aqueous solution for preparing 30 parts, is slowly added into above-mentioned solution, is stirred 0.5-5 hours, removal
Moisture in mixed solution；
（3）The compound of acquisition is subjected to high temperature sintering and by sintered product grind into powder.
3. carbon nitride precursor as claimed in claim 2 includes but not limited in cyanamide, dicyandiamide, melamine, urea
It is one or more.
4. a concentration of 0.1-10M of calcium nitrate as claimed in claim 2 and diammonium hydrogen phosphate.
5. mixed solution moisture removal mode as claimed in claim 2 includes the lower heating evaporation of stirring or freeze-drying.
6. sintering process as claimed in claim 2：Heating rate is 1-10 DEG C/min, is kept under the conditions of 350 DEG C -600 DEG C
1-4 hour.
7. hydroxyapatite as described in claim 1/carbonitride fluorescent nanometer composite particle application field is drug, gene load
Body or bioprobe.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810233051.7A CN108324949B (en) | 2018-03-21 | 2018-03-21 | Hydroxyapatite-carbon nitride composite particle and in-situ composite process thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810233051.7A CN108324949B (en) | 2018-03-21 | 2018-03-21 | Hydroxyapatite-carbon nitride composite particle and in-situ composite process thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108324949A true CN108324949A (en) | 2018-07-27 |
| CN108324949B CN108324949B (en) | 2021-04-13 |
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ID=62931017
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| CN201810233051.7A Active CN108324949B (en) | 2018-03-21 | 2018-03-21 | Hydroxyapatite-carbon nitride composite particle and in-situ composite process thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112661229A (en) * | 2020-11-27 | 2021-04-16 | 商丘师范学院 | Has the function of heavy metal ion adsorptionAnd the visible light photocatalytic performance of HA/g-C3N4Method for preparing composite material |
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