CN105778020A - Preparation method of water-soluble ferromagnetic nanoparticles - Google Patents
Preparation method of water-soluble ferromagnetic nanoparticles Download PDFInfo
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- CN105778020A CN105778020A CN201610212633.8A CN201610212633A CN105778020A CN 105778020 A CN105778020 A CN 105778020A CN 201610212633 A CN201610212633 A CN 201610212633A CN 105778020 A CN105778020 A CN 105778020A
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- 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
- C08F292/00—Macromolecular compounds obtained by polymerising monomers on to inorganic materials
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- 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
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Abstract
The invention relates to a preparation method of water-soluble ferromagnetic nanoparticles.A series of water-soluble nanoparticles with different electrostatic and hydrophobic properties are prepared by means of atom transfer radical polymerization, and the biological properties of magnetic nanoparticles can be optimized and regulated by means of differences of different hydrophobic effects on biological properties such as biomass separation, cell and organism ingestion, bacterium resisting, medicine carrying and the like.The method is easy to control and has a wide application prospect and research and development value in the aspects of treatment and diagnosis.
Description
Technical field
The present invention relates to a kind of novel high polymer material technology, be specially and use atom transfer radical polymerization synthesis
A series of water soluble nanometer particles with different electrostatic-hydrophobic performance, belong to new material technology field.
Background technology
In recent years, the behavior of magnetic nano-particle and extensively closing the multi-field the most studied personnel of application
Note.In the research of magnetic nano-particle, synthesis condition and surface modification to magnetic nano-particle are to closing weight
Want, because which dictates that their physicochemical property, granule stability and biological activity.There is suitable physics and chemistry
The magnetic nano-particle of character and modification rear surface performance is in medicine carrying, hyperthermia, nuclear magnetic resonance, NMR, tissue work
Journey and reparation, biosensor, bio-chemistry separation and analysis etc. are multi-field achieves extensively application.
Atom transfer radical polymerization be with simple organohalogen compounds as initiator, transient metal complex is as halogen
Atom carrier, by redox reaction, is mainly initiator halogenated hydrocarbons by chain transmission free radical and hypopus
(R-X) dynamic equilibrium and set up between macromolecule product (R-Pn-X) realizes the control to polyreaction.
Atom transfer radical polymerization can be used for modified Nano particle, improves stability and dispersibility, at preparation hydridization material
Material aspect is achieved with extensively application.
When polyelectrolyte interacts with protein and other and the biologic artifact such as antibacterial, cell,
Electrostatic interaction and hydrophobic interaction are the most complementary, and research finds, hydrophobic interaction can be main to electrostatic interaction
The polyelectrolyte led-biomass interact and play regulation and control and amplification, and then affect polyelectrolyte, modification
The biological property of polyelectrolyte nanoparticle.
Present invention employs a kind of new method, i.e. the synthesis of utilization atom transfer radical polymerization is a series of has difference
The water soluble nanometer particles of electrostatic-hydrophobic performance, utilizes different hydrophobic interaction in biomass separation, cell and life
The difference of the biological properties such as object absorption, antibacterial, medicine carrying, can carry out optimum to magnetic nano-particle biological property
Change and regulation and control.This preparation method is easily controllable, has broad application prospects and researches and develops value.
Summary of the invention
In view of problem above, it is an object of the invention to provide a kind of magnetic nanometer is that platform synthesis has difference
The nanoparticle of hydrophobic performance, structure can be in conjunction with magnetic responsiveness, T2The characteristics such as imaging characteristic, fluorescence response
Novel magnetic nanometer system, has potential answering in fields such as nuclear magnetic resonance, biomass separation, drug releases
By value.Concrete technical scheme is as follows:
The preparation method of a kind of water-soluble iron magnetic nanometer, comprises the steps:
(1) the Oil-based magnetic nanoparticle of monolayer oleic acid modified is prepared by coprecipitation: by FeCl3·6H2O
And FeSO4·4H2O is dissolved in deionized water, rapidly joins ammonia, temperature under nitrogen protection at 78～82 DEG C
It is added dropwise over oleic acid after Wen Ding and stirs 80～100min, preparing the water-based magnetic fluid of double-deck oleic acid modified；
The water-based magnetic fluid of described double-deck oleic acid modified and toluene solution are mixed and added into separatory extraction after NaCl
Take, divide water backflow except water 3～4h the most afterwards, prepare the Oil-based magnetic nanoparticle of monolayer oleic acid modified；
Described FeSO4·4H2O and FeCl3·6H2O mass ratio is 1:1.75～1.8；
Described FeSO4·4H2O is 1:25～30 with the mass ratio of deionized water；
Described ammonia is 1:3.8～4 with the volume ratio of deionized water；
Described toluene is 1:1.8～2 with the volume ratio of the water-based magnetic fluid of described double-deck oleic acid modified；
Described sodium chloride and toluene solution mass ratio are 1:3.5～4；
(2) prepare, by ligand exchange method, the Oil-based magnetic nanoparticle that silane coupler is modified: take bromine isobutyl
Base acylbromide is dissolved in dichloromethane, is slowly dropped into two containing 3-aminopropyl triethoxysilane and triethylamine under ice bath
In chloromethanes solution, controlling rate of addition is 6～8 seconds/；Drip complete, under room temperature, continue reaction 4 hours
Rear sucking filtration, washs head product with hydrochloric acid solution, sodium chloride solution and water, then with anhydrous magnesium sulfate be dried 45～
60 minutes, 25～30 DEG C of backspins steamed 20～30 minutes, prepare bromine isobutyl group silane coupler BMTP；
The Oil-based magnetic that described bromine isobutyl group silane coupler, triethylamine are dissolved in described monolayer oleic acid modified is received
In the toluene dispersion liquid of rice corpuscles, stirred under nitrogen atmosphere 48～50h, reaction adds petroleum ether precipitation after terminating
And be again dispersed in toluene, the most afterwards product is dissolved in dimethylformamide, at dimethyl formyl
Amine is dialysed 70～72 hours, obtains the Oil-based magnetic nanoparticle that silane coupler is modified；
The volume ratio of described bromine isobutyl group acylbromide, 3-aminopropyl triethoxysilane, triethylamine and dichloromethane is
1:1.8～2:1.8～2:12；
The volume ratio of described dichloromethane, hydrochloric acid solution, sodium chloride brine and water is 1:1.2:1.2:1.2；
Described bromine isobutyl group silane coupler, triethylamine, the Oil-based magnetic nanoparticle of described monolayer oleic acid modified
Mass ratio be 1:1.7～1.8:190～195；
(3) the ferromagnetic nanoparticle of water solublity that atom transfer radical polymerization is modified is utilized for PDMAEMA
Son: Oil-based magnetic nanoparticle that described silane coupler is modified, polymerization monomer DMAEMA, part
HMTETA is dissolved in dimethylformamide, after logical nitrogen drives oxygen at least 1 hour, adds CuCl in nitrogen stream
And CuCl2, it is warming up to 90～95 DEG C, after reacting 24～30 hours in nitrogen environment, by head product at DMF
Middle dialysis is dialysed three days after one day in water, product lyophilizing of dialysing, and produces the water base of PDMAEMA modification
Magnetic nano-particle；
Described part HMTETA, the volume ratio of polymerization monomer DMAEMA are 1:200～250；
Described CuCl2, the mass ratio of CuCl be 1:4～4.5；
The mass ratio of the Oil-based magnetic nanoparticle that described polymerization monomer DMAEMA, silane coupler are modified is
1:9.5～10.
This preparation method also includes utilizing the water-soluble of the different different electrostatic-hydrophobic performance of halogenated hydrocarbons quaternization preparation
The ferromagnetic nanoparticle of property: the water-base magnetic nanoparticle dissolution that described PDMAEMA is modified in isopropanol,
React 24～30 hours under the conditions of lucifuge after adding the halogenated hydrocarbons of different chain length；Product is dialysed in isopropanol
After within 45～48 hours, final vacuum is dried 12～15 hours, it is dissolved in water, and filters three times with 450nm filter,
The water-soluble iron magnetic nanometer of different electrostatic-hydrophobic performance is obtained after lyophilizing.
Water-base magnetic nanoparticle, the mass ratio of isopropanol that described PDMAEMA modifies are 1:180～200；
Described isopropanol is 1:1～1.1 with the volume ratio of halogenated hydrocarbons；The mass fraction of described ammonia is 23～25%；
The pH value of described hydrochloric acid is 2～3；The concentration of described sodium chloride solution is 90～100mM.
The halogenated hydrocarbons of described different chain length is gentle selected from bromoethane, n-butyl bromide, bromohexane, bromooctane, bromine last of the ten Heavenly stems, bromine
Change benzyl, bromoethanol.
The innovative point of the present invention is to have employed a kind of new preparation method, has with magnetic nanometer for platform construction
There is the nanoparticle of different hydrophobic performance.This preparation method is simple and efficient and easily controllable, has wide application
Prospect, especially is expected to be applied further in treatment diagnostics.
Accompanying drawing explanation
Fig. 1 is that the ferromagnetic nanoparticle of oil base of the monolayer oleic acid modified of embodiment 1 preparation is at transmission electron microscope
Under observed image；Wherein, (a) be Oil-based magnetic nanoparticle observed image under transmission electron microscope,
B () is the particle diameter distribution that transmission electron microscopy observation obtains；
Fig. 2 is the ferromagnetic nanoparticle aqueous solution picture of the PDMAEMA modification of embodiment 3 preparation；
Fig. 3 is that the water-soluble iron magnetic nanometer of the PDMAEMA modification of embodiment 3 preparation is at transmitted electron
The observed image of different amplification under microscope；Wherein, (a) is the water-soluble iron that PDMAEMA modifies
Magnetic nanometer population distribution image under transmission electron microscopy observation, (b) are that PDMAEMA modifies
Water-soluble iron magnetic nanometer local distribution image under transmission electron microscopy observation；
Fig. 4 be the difference of embodiment 4 preparation hydrophobic-size of the ferromagnetic nanoparticle of antistatic property and surface charge
Distributed image；Wherein, (a) after being bromoethane quaternization the distribution of sizes of ferromagnetic nanoparticle, (b) be bromine
The zeta current potential of ferromagnetic nanoparticle after ethane quaternization.
Detailed description of the invention
Below, further illustrate present invention by embodiment, but protection scope of the present invention is not limited in
Embodiment.Those skilled in the art is made in the case of without departing substantially from spirit and scope of the present invention its
Changing and modifications of it, within being included in scope.
Embodiment 1
By FeCl3·6H2O and FeSO4·4H2O is soluble in water with mass ratio 1:1.75, and nitrogen protects lower 80 DEG C
Under rapidly join ammonia, be added dropwise over oleic acid after temperature stabilization, oleic acid is 1:20 with ammonia, the volume ratio of water:
100, after stirring one hour, prepare the water-based magnetic fluid of double-deck oleic acid modified.Oleic acid modified by above-mentioned preparation
The separatory extraction after 2:1 is mixed and added into NaCl by volume of magnetic nanometer and toluene solution, in triplicate
Rear point of water backflow removes water 3 hours, prepares the Oil-based magnetic nanoparticle of monolayer oleic acid modified.
Product carries out TEM electronic microscope photos after having prepared, result display magnetic nano-particle is in toluene solution
Show good dispersibility, do not have obvious agglomerated particles to occur, utilize Nano Measurer computer to unite
Meter obtains grain size of magnetic nanometer grains and is mostly distributed between 11～12nm, all in superparamagnetic nanoparticle size
In the range of, as shown in Figure 1.
Embodiment 2
Take bromine isobutyl group acylbromide 1:3 by volume and be dissolved in dichloromethane, under ice bath, be slowly dropped into 3-aminopropyl
Triethoxysilane, triethylamine dichloromethane solution in.Controlling rate of addition is 7 seconds/, after dripping
Under room temperature continue reaction 4 hours after sucking filtration, by volume 1:1:1 hydrochloric acid solution, sodium chloride solution and
After water washing sucking filtration after head product 2 times, being dried one hour with anhydrous magnesium sulfate, 37 DEG C of backspins steam half an hour, system
Standby bromine isobutyl group silane coupler BMTP；Take bromine isobutyl group silane coupler, triethylamine is dissolved in monolayer oleic acid
In the toluene dispersion liquid of the Oil-based magnetic nanoparticle modified, mass ratio is respectively 1:1.7:190, and nitrogen is protected
Protecting lower stirring 48h, reaction adds petroleum ether precipitation after terminating and is again dispersed in toluene, the most afterwards will
Product is dissolved in dimethylformamide, dialyses three days in dimethylformamide, prepares silane coupler and modifies
Oil-based magnetic nanoparticle.
Embodiment 3
Part HMTETA, polymerization monomer DMAEMA 1:200 by volume are dissolved in silane coupler
In the dimethyl formamide solution of modified Oil-based magnetic nanoparticle, DMAEMA is with silane coupler modified
The mass ratio of Oil-based magnetic nanoparticle be 1:10.After logical nitrogen drives oxygen 1 hour, by quality in nitrogen stream
CuCl is added than 1:42And CuCl, it is warming up to 90 DEG C, after reacting 24 hours in nitrogen environment, will just
Product is dialysed three days after dialysing in DMF one day in water, product lyophilizing of dialysing, and produces PDMAEMA
The water-base magnetic nanoparticle modified.
Lyophilizing after product dialysis, it is thus achieved that water solublity, as shown in Figure 2.
This example product carries out TEM electronic microscope photos after having prepared, result display magnetic nano-particle is aobvious in water
Shown good dispersibility, the most significantly reunite appearance, size and pattern before polymerization after occur substantially
Change, as shown in Figure 3.
Embodiment 4
Take magnetic nano-particle that PDMAEMA modifies during 1:200 is dissolved in isopropanol in mass ratio, add
React under the conditions of the halogenated hydrocarbons lucifuge of the different chain length of 1:1 addition by volume under the conditions of lucifuge after round-bottomed flask
After 24 hours, vacuum drying 12 hours two days later of dialysing in isopropanol, head product is dissolved in water, uses
450nm filter filters three times, obtains the water-soluble iron magnetic nanometer of different electrostatic-hydrophobic performance after lyophilizing.
After product lyophilizing, it is carried out particle diameter and zeta potentiometric analysis, particle diameter can be clearly observable left at 80nm
The right side, zeta current potential is at about 40mV, as shown in Figure 4.
Claims (4)
1. the preparation method of a water-soluble iron magnetic nanometer, it is characterised in that comprise the steps:
(1) the Oil-based magnetic nanoparticle of monolayer oleic acid modified is prepared by coprecipitation: by FeCl3·6H2O
And FeSO4·4H2O is dissolved in deionized water, rapidly joins ammonia, temperature under nitrogen protection at 78～82 DEG C
It is added dropwise over oleic acid after Wen Ding and stirs 80～100min, preparing the water-based magnetic fluid of double-deck oleic acid modified；
The water-based magnetic fluid of described double-deck oleic acid modified and toluene solution are mixed and added into separatory extraction after NaCl
Take, divide water backflow except water 3～4h the most afterwards, prepare the Oil-based magnetic nanoparticle of monolayer oleic acid modified；
Described FeSO4·4H2O and FeCl3·6H2O mass ratio is 1:1.75～1.8；
Described FeSO4·4H2O is 1:25～30 with the mass ratio of deionized water；
Described ammonia is 1:3.8～4 with the volume ratio of deionized water；
Described toluene is 1:1.8～2 with the volume ratio of the water-based magnetic fluid of described double-deck oleic acid modified；
Described sodium chloride and toluene solution mass ratio are 1:3.5～4；
(2) prepare, by ligand exchange method, the Oil-based magnetic nanoparticle that silane coupler is modified: take bromine isobutyl
Base acylbromide is dissolved in dichloromethane, is slowly dropped into two containing 3-aminopropyl triethoxysilane and triethylamine under ice bath
In chloromethanes solution, controlling rate of addition is 6～8 seconds/；Drip complete, under room temperature, continue reaction 4 hours
Rear sucking filtration, washs head product with hydrochloric acid solution, sodium chloride solution and water, then with anhydrous magnesium sulfate be dried 45～
60 minutes, 25～30 DEG C of backspins steamed 20～30 minutes, prepare bromine isobutyl group silane coupler BMTP；
The Oil-based magnetic that described bromine isobutyl group silane coupler, triethylamine are dissolved in described monolayer oleic acid modified is received
In the toluene dispersion liquid of rice corpuscles, stirred under nitrogen atmosphere 48～50h, reaction adds petroleum ether precipitation after terminating
And be again dispersed in toluene, the most afterwards product is dissolved in dimethylformamide, at dimethyl formyl
Amine is dialysed 70～72 hours, obtains the Oil-based magnetic nanoparticle that silane coupler is modified；
The volume ratio of described bromine isobutyl group acylbromide, 3-aminopropyl triethoxysilane, triethylamine and dichloromethane is
1:1.8～2:1.8～2:12；
The volume ratio of described dichloromethane, hydrochloric acid solution, sodium chloride brine and water is 1:1～1.2:1～1.2:
1～1.2；
Described bromine isobutyl group silane coupler, triethylamine, the Oil-based magnetic nanoparticle of described monolayer oleic acid modified
Mass ratio be 1:1.7～1.8:190～195；
(3) the ferromagnetic nanoparticle of water solublity that atom transfer radical polymerization is modified is utilized for PDMAEMA
Son: Oil-based magnetic nanoparticle that described silane coupler is modified, polymerization monomer DMAEMA, part
HMTETA is dissolved in dimethylformamide, and logical nitrogen drives oxygen at least one hour, adds CuCl in nitrogen stream
And CuCl2, it is warming up to 90～95 DEG C, after reacting 24～30 hours in nitrogen environment, by head product at DMF
Middle dialysis is dialysed three days after one day in water, product lyophilizing of dialysing, and produces the water base of PDMAEMA modification
Magnetic nano-particle；
Described part HMTETA, the volume ratio of polymerization monomer DMAEMA are 1:200～250；
Described CuCl2, the mass ratio of CuCl be 1:4～4.5；
The mass ratio of the Oil-based magnetic nanoparticle that described polymerization monomer DMAEMA, silane coupler are modified is
1:9.5～10.
Preparation method the most according to claim 1, it is characterised in that also include utilizing different halogenated hydrocarbons quaternary ammonium
The water-soluble iron magnetic nanometer of the different electrostatic-hydrophobic performance of salinization preparation: described PDMAEMA is modified
Water-base magnetic nanoparticle dissolution, in isopropanol, is reacted under the conditions of lucifuge after adding the halogenated hydrocarbons of different chain length
24～30 hours；Product 45～48 hours final vacuums of dialysing in isopropanol are dried 12～15 hours, dissolve
In water, and filter three times with 450nm filter, after lyophilizing, obtain the water-soluble iron of different electrostatic-hydrophobic performance
Magnetic nanometer.
Preparation method the most according to claim 2, it is characterised in that it is water base that described PDMAEMA modifies
Magnetic nano-particle, the mass ratio of isopropanol are 1:180～200；Described isopropanol and the volume ratio of halogenated hydrocarbons
For 1:1～1.1；The mass fraction of described ammonia is 23～25%；The pH value of described hydrochloric acid is 2～3；Institute
The concentration stating sodium chloride solution is 90～100mM.
4. according to the preparation method described in Claims 2 or 3, it is characterised in that the halogenated hydrocarbons of described different chain length
Gentle, cylite, bromoethanol selected from bromoethane, n-butyl bromide, bromohexane, bromooctane, bromine last of the ten Heavenly stems.
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| CN107039139A (en) * | 2017-05-04 | 2017-08-11 | 绵阳市宏扬科技有限公司 | A kind of preparation method of magnetic fluid and its magnetic fluid of preparation |
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