CN104497235B - Temperature responsive fluorescent carbon nanoparticle hybrid microgel and preparation method thereof - Google Patents
Temperature responsive fluorescent carbon nanoparticle hybrid microgel and preparation method thereof Download PDFInfo
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- 239000011852 carbon nanoparticle Substances 0.000 title claims abstract description 53
- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 35
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
- 238000003756 stirring Methods 0.000 claims abstract description 9
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims abstract description 8
- 150000001263 acyl chlorides Chemical class 0.000 claims abstract description 7
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 7
- 239000000178 monomer Substances 0.000 claims abstract description 7
- 239000000706 filtrate Substances 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 239000003999 initiator Substances 0.000 claims abstract description 6
- 238000010992 reflux Methods 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 5
- 239000000243 solution Substances 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000002245 particle Substances 0.000 claims description 8
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 8
- 235000019394 potassium persulphate Nutrition 0.000 claims description 8
- 239000008187 granular material Substances 0.000 claims description 7
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 6
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical group ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000385 dialysis solution Substances 0.000 claims description 5
- 239000012153 distilled water Substances 0.000 claims description 5
- 239000000499 gel Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000003763 carbonization Methods 0.000 claims description 4
- 238000001027 hydrothermal synthesis Methods 0.000 claims description 4
- 108010010803 Gelatin Proteins 0.000 claims description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 239000008273 gelatin Substances 0.000 claims description 2
- 229920000159 gelatin Polymers 0.000 claims description 2
- 235000019322 gelatine Nutrition 0.000 claims description 2
- 235000011852 gelatine desserts Nutrition 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 claims description 2
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 claims description 2
- 229910001873 dinitrogen Inorganic materials 0.000 claims 1
- 238000000502 dialysis Methods 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 4
- 238000001816 cooling Methods 0.000 abstract description 3
- 239000000047 product Substances 0.000 abstract description 2
- 238000005303 weighing Methods 0.000 abstract 3
- 239000012295 chemical reaction liquid Substances 0.000 abstract 1
- 239000007810 chemical reaction solvent Substances 0.000 abstract 1
- 238000013270 controlled release Methods 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 4
- 230000003313 weakening effect Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 239000000017 hydrogel Substances 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007863 gel particle Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
Landscapes
- Carbon And Carbon Compounds (AREA)
Abstract
The invention relates to a temperature responsive fluorescent carbon nanoparticle hybrid microgel and a preparation method thereof. The method comprises the following steps: (1) weighing a proper amount of fluorescent carbon nanoparticles, preparing a fluorescent carbon nanoparticle solution by using dichloromethane, adding an acyl chloride monomer, reacting for 10 hours at room temperature, removing a reaction solvent, adding and spin-drying; (2) weighing the obtained double-bond fluorescent carbon nanoparticles and dispersing and dissolving in the fluorescent carbon nanoparticles; and transferring into a reaction container, introducing nitrogen to discharge air, adding a crosslinking agent, sodium dodecyl sulfate and refined N-isopropylacrylamide and stirring; introducing nitrogen, heating, and when the reaction liquid flows back, weighing an initiator and adding the initiator into a three-necked flask; (3) continuously introducing nitrogen and stirring; carrying out reflux react for 5-16 hours at 50-90 DEG C, and then stopping reaction; and (4) cooling to room temperature, filtering, and taking the filtrate and carrying out dialysis for 48 hours. The product prepared by the method is non-toxic, has a very good temperature response by fluorescence and has a good application prospect in drug controlled release, temperature sensing and the like.
Description
Technical field
The present invention relates to chemical technology field, particularly to a kind of fluorescence carbon nano-particle hybrid microgel of temperature-responsive
And preparation method thereof.
Technical background
Microgel (microgel) is the highly cross-linked polymeric colloid particle of intramolecular, and its internal structure is typical three
Dimension network structure.The nano microgel of generally preparation is all the high degree of dispersion system being swollen in colloidal form in certain solvent,
This system is referred to as nano-hydrogel dispersion.Microgel (hydrogel) is that one kind can save large quantity of moisture and significantly swelling
Hydrophilic gel.Because typically containing hydrophilic group in structure, such as-conh2、-cooh、-so3H etc..Most microgel nets
The water reaching macromolecule weight several times itself to hundreds times can be saved in shape space.Because microgel carries a large amount of functional groups,
These microgels generally have environment (such as ph, temperature) stimuli responsive performance, and that is, its volume can be grown up with the change of environment
Or reduce.Because micro-gel surface absorption property is strong, specific surface area big, functional diversity, gel particle size are controlled, structure composition
The various features such as can design so as to have extensively in various fields such as medicine transmission, civil construction, food fresh keeping, fire-fighting, sewage disposals
General potential using value.However, existing response microgel generally only has volume response, that is, during environmental change, it is it
Volume responds to environmental change, this greatly limits the practical application of microgel.Therefore, using new material new method Lai
New response microgel is prepared in design, can be preferably applied for a lot of fields, develops new response microgel
Become one of the focus direction in research hydrogel field.
Content of the invention
The invention provides fluorescence carbon nano-particle hybrid microgel of a kind of temperature-responsive and preparation method thereof, prepared
The fluorescence of fluorescence carbon nano-particle hybrid microgel has good temperature-responsive, in medicine controlled releasing, temperature sensing, organizational project
Etc. aspect have good application prospect.
The technical scheme is that a kind of preparation method of the fluorescence carbon nano-particle hybrid microgel of temperature-responsive,
Comprise the following steps:
(1) weigh appropriate fluorescence carbon nano-particle, with dichloromethane dissolving, being configured to concentration is the glimmering of 0.5-10mg/ml
Light carbon granule solution, adds acyl chloride monomer, reacts 10h at room temperature, removes reaction dissolvent, adds water, be then spin-dried for, and obtains double
Key fluorescence carbon nano-particle；
(2) weigh double bond fluorescence carbon nano-particle, add dispersing and dissolving in 100ml distilled water；And be transferred into filling
Have in the there-necked flask of agitator, reflux condensing tube and thermometer；Open agitator, and uniformly lead to nitrogen, be completely exhausted out container and
Air in solution, adds cross-linking agent, dodecyl sodium sulfate (sds), refined n- N-isopropylacrylamide；Stirring, and continue
Continuous logical nitrogen, is completely exhausted out the air in container and solution, heating, after question response liquid starts backflow, weigh initiator and by its
Add in there-necked flask；
(3) continuously stirred and logical nitrogen, stopped reaction after continuing back flow reaction 5-16h at 50-90 DEG C;
(4) filter after being cooled to room temperature, take filtrate, dialyse 48h, it is miscellaneous that gained dialysis solution is the good carbon nano-particle of purification
Change microgel.
In step (1), described fluorescence carbon nano-particle, the mass ratio of acyl chloride monomer are 10:1-50:1.
In step (1), described fluorescence carbon nano-particle is hydro-thermal method carbonization glucose, cellulose, shitosan, edta
2na, edta or the fluorescence carbon nano-particle of gelatin preparation.It is preferably the fluorescent carbon nanometer of hydro-thermal method carbonization edta 2na preparation
Granule.
In step (1), described acyl chloride monomer is acryloyl chloride, methacrylic chloride, crotonyl chloride.Preferably acryloyl
Chlorine.
In step (2), double bond fluorescence carbon nano-particle consumption is 1-40 weight portion, n- N-isopropylacrylamide consumption
For 100-400 weight portion, sodium lauryl sulphate consumption is 1-20 weight portion, and potassium peroxydisulfate consumption is 1-10 weight portion.Double bond
Change fluorescence carbon granule, the mass ratio that feeds intake of n- N-isopropylacrylamide is 1:2.5-1:400, preferred mass ratio is for 1:10.
In step (2), described initiator has hydrogen peroxide, Ammonium persulfate. or potassium peroxydisulfate.Preferably potassium peroxydisulfate.
In step (2), described cross-linking agent has n-n methylene-bisacrylamide.
In step (3), preferable reaction temperature is 70 DEG C, preferred reaction time 12h.
The present invention also provides a kind of fluorescence carbon nano-particle hybrid microgel product as said method preparation.
Fluorescence carbon nano-particle hybrid microgel particle diameter that the present invention is obtained is in 300nm；When Same Wavelength excites,
Temperature raises, fluorescent weakening；Conversely, Fluorescence Increasing, its fluorescence has good temperature-responsive.It passes in medicine controlled releasing, temperature
The aspects such as sense, organizational project have good application prospect.
Brief description
Fig. 1 is that the scanning electron microscope collection of illustrative plates of the fluorescence carbon nano-particle hybrid microgel of temperature-responsive of embodiment 3 preparation is (flat
All particle diameters are about 300nm)
Fig. 2 is the temperature-responsive of the fluorescence carbon nano-particle hybrid microgel aqueous solution of temperature-responsive of embodiment 1 preparation
Fluorescence pattern (temperature raises, fluorescent weakening, conversely, Fluorescence Increasing, excitation wavelength is 320nm).
Fig. 3 is the temperature-responsive of the fluorescence carbon nano-particle hybrid microgel aqueous solution of temperature-responsive of embodiment 2 preparation
Fluorescence pattern (temperature raises, fluorescent weakening, conversely, Fluorescence Increasing, excitation wavelength is 320nm).
Fig. 4 is the temperature-responsive of the fluorescence carbon nano-particle hybrid microgel aqueous solution of temperature-responsive of embodiment 3 preparation
Fluorescence pattern (temperature raises, fluorescent weakening, conversely, Fluorescence Increasing, excitation wavelength is 320nm).
Specific embodiment
Exemplarily describe the present invention with reference to non-limiting specific embodiment further in detail.The embodiment of the present invention
Used in reagent remove fluorescence carbon nano-particle (according to liao b.; long, p.; he, b.; yi, s.; ou, b.;
shen, s.;Chen, j. j mater chem c 2013, prepares described in 1,3716), remaining is all commercially available to obtain.
Embodiment 1:
Weigh appropriate fluorescence carbon nano-particle 100mg, with dichloromethane dissolving, being configured to concentration is 0.5-10mg/ml's
Fluorescent carbon particle solution.Add acryloyl chloride 5mg.React 10h at room temperature, afterwards reaction dissolvent is removed, add water, after being spin-dried for
Obtain double bond fluorescence carbon nano-particle.
Weigh double bond fluorescence carbon granule 15mg, add dispersing and dissolving in 100ml distilled water, and be transferred into equipped with stirring
Mix in the there-necked flask of device, reflux condensing tube and thermometer.Open agitator, and uniformly lead to nitrogen, be completely exhausted out container and solution
In air.5mg cross-linking agent n-n methylene-bisacrylamide, 5mg dodecyl sodium sulfate (sds), 200mg is added to refine
N- N-isopropylacrylamide.Continue logical nitrogen, be completely exhausted out the air in container and solution.Heating, after reactant liquor backflow, will
7mg potassium peroxydisulfate adds in there-necked flask, is sufficiently stirred for.Maintaining nitrogen purge, stopped reaction after continuing back flow reaction 12h at 60 DEG C,
Filter after being cooled to room temperature, take filtrate to be placed in dialysis 48h in bag filter, it is miscellaneous that gained dialysis solution is the good carbon nano-particle of purification
Change microgel.
Embodiment 2:
Weigh appropriate fluorescence carbon nano-particle 100mg, with dichloromethane dissolving, being configured to concentration is 0.5-10mg/ml's
Fluorescent carbon particle solution.Add acryloyl chloride 10mg.React 10h at room temperature, afterwards reaction dissolvent is removed, add water, be spin-dried for
After obtain double bond fluorescence carbon nano-particle.
Weigh double bond fluorescence carbon granule 25mg, add dispersing and dissolving in 100ml distilled water, and be transferred into equipped with stirring
Mix in the there-necked flask of device, reflux condensing tube and thermometer.Open agitator, and uniformly lead to nitrogen, be completely exhausted out container and solution
In air.10mg cross-linking agent n-n methylene-bisacrylamide, 10mg dodecyl sodium sulfate (sds), 200mg is added to refine
N- N-isopropylacrylamide.Continue logical nitrogen, be completely exhausted out the air in container and solution.Heating, after reactant liquor backflow, will
7mg potassium peroxydisulfate adds in there-necked flask.Maintaining nitrogen purge and stirring, stopped reaction after continuing back flow reaction 10h at 80 DEG C, cooling
Filter to room temperature, take filtrate to be placed in dialysis 48h in bag filter, it is micro- that gained dialysis solution is the good carbon nano-particle hydridization of purification
Gel.
Embodiment 3:
Weigh appropriate fluorescence carbon nano-particle 200mg, with dichloromethane dissolving, being configured to concentration is 0.5-10mg/ml's
Fluorescent carbon particle solution.Add acryloyl chloride 10mg.React 10h at room temperature, afterwards reaction dissolvent is removed, add water, be spin-dried for
After obtain double bond fluorescence carbon nano-particle.
Weigh double bond fluorescence carbon granule 20mg, add dispersing and dissolving in 100ml distilled water, and be transferred into equipped with stirring
Mix in the there-necked flask of device, reflux condensing tube and thermometer.Open agitator, and uniformly lead to nitrogen, be completely exhausted out container and solution
In air.5mg cross-linking agent n-n methylene-bisacrylamide, 15mg dodecyl sodium sulfate (sds), 200mg is added to refine
N- N-isopropylacrylamide.Continue logical nitrogen, be completely exhausted out the air in container and solution.Heating, after reactant liquor backflow, will
7mg potassium peroxydisulfate adds in there-necked flask.Maintaining nitrogen purge, stirring, stopped reaction after continuing back flow reaction 12h at 70 DEG C, cooling
Filter to room temperature, take filtrate to be placed in dialysis 48h in bag filter, it is micro- that gained dialysis solution is the good carbon nano-particle hydridization of purification
Gel.
Claims (9)
1. a kind of preparation method of the fluorescence carbon nano-particle hybrid microgel of temperature-responsive is it is characterised in that include following walking
Rapid:
(1) weigh appropriate fluorescence carbon nano-particle, with dichloromethane dissolving, be configured to the fluorescent carbon that concentration is 0.5-10mg/ml
Particle solution, adds acyl chloride monomer, reacts 10h at room temperature, removes reaction dissolvent, adds water, be then spin-dried for, obtain double bond
Fluorescence carbon nano-particle；Described acyl chloride monomer is acryloyl chloride, methacrylic chloride, crotonyl chloride；
(2) weigh double bond fluorescence carbon nano-particle, add dispersing and dissolving in 100ml distilled water；And it is transferred into equipped with stirring
Mix in the there-necked flask of device, reflux condensing tube and thermometer；Open agitator, and uniformly lead to nitrogen, be completely exhausted out container and solution
In air, add cross-linking agent, dodecyl sodium sulfate, refined n- N-isopropylacrylamide；Continuously stirred, and continue logical nitrogen
Gas, is completely exhausted out the air in container and solution, heating, after question response liquid starts backflow, weighs initiator and is added into three
In mouth bottle；
(3) continuously stirred with logical nitrogen, after continuing back flow reaction 5-16h at 50-90 DEG C, stopped reaction；
(4) filter after being cooled to room temperature, take filtrate, dialyse 48h, it is micro- that gained dialysis solution is the good carbon nano-particle hydridization of purification
Gel.
2. the preparation method of the fluorescence carbon nano-particle hybrid microgel of temperature-responsive according to claim 1, its feature
It is, in step (1), described fluorescence carbon nano-particle is 10:1-50:1 with the mass ratio of acyl chloride monomer.
3. the preparation method of the fluorescence carbon nano-particle hybrid microgel of temperature-responsive according to claim 1, its feature
Be, in step (1), described fluorescence carbon nano-particle be hydro-thermal method carbonization glucose, cellulose, shitosan, edta 2na,
Edta or the fluorescence carbon nano-particle of gelatin preparation.
4. the preparation method of the fluorescence carbon nano-particle hybrid microgel of the temperature-responsive according to claim 1 or 3, it is special
Levy and be, in step (1), described fluorescence carbon nano-particle is the fluorescence carbon nano-particle of hydro-thermal method carbonization edta 2na preparation.
5. the preparation method of the fluorescence carbon nano-particle hybrid microgel of temperature-responsive according to claim 1, its feature
It is, in step (2), double bond fluorescent carbon amount of particles is 1-40 weight portion, and n- N-isopropylacrylamide consumption is 100-
400 weight portions, dodecyl sodium sulfate consumption is 1-20 weight portion, and potassium peroxydisulfate consumption is 1-10 weight portion.
6. the preparation method of the fluorescence carbon nano-particle hybrid microgel of temperature-responsive according to claim 1 or 5, it is special
Levy and be, double bond fluorescence carbon granule is optimum with the mass ratio that feeds intake of n- N-isopropylacrylamide to be 1:10.
7. the preparation method of the fluorescence carbon nano-particle hybrid microgel of temperature-responsive according to claim 1, its feature
It is, in step (2), described initiator has hydrogen peroxide, Ammonium persulfate. or potassium peroxydisulfate.
8. the preparation method of the fluorescence carbon nano-particle hybrid microgel of a kind of temperature-responsive according to claim 1, its
It is characterised by, in step (3), back flow reaction optimum temperature is 70 DEG C, optimum reacting time is 12h.
9. a kind of temperature response type fluorescence carbon nano-particle hybrid microgel of the method for claim 1 preparation.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101775112A (en) * | 2010-02-05 | 2010-07-14 | 苏州大学 | Preparation method of magnetic fluorescence dual functional thermo-sensitive nano particle |
| WO2013192629A1 (en) * | 2012-06-22 | 2013-12-27 | William Marsh Rice University | Temperature responsive nanoparticles for magnetically detecting hydrocarbons in geological structures |
| CN103769052A (en) * | 2014-02-28 | 2014-05-07 | 广东药学院 | Magnetism and temperature double-responded mesoporous carbon material as well as preparation method and application thereof |
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| CN101775112A (en) * | 2010-02-05 | 2010-07-14 | 苏州大学 | Preparation method of magnetic fluorescence dual functional thermo-sensitive nano particle |
| WO2013192629A1 (en) * | 2012-06-22 | 2013-12-27 | William Marsh Rice University | Temperature responsive nanoparticles for magnetically detecting hydrocarbons in geological structures |
| CN103769052A (en) * | 2014-02-28 | 2014-05-07 | 广东药学院 | Magnetism and temperature double-responded mesoporous carbon material as well as preparation method and application thereof |
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