CN102060948A - Method for preparing polymer fluorescent nano particle - Google Patents
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Abstract
The invention relates to a method for preparing a polymer fluorescent nano particle, which belongs to the field of materials. The invention solves the problems that the traditional polymer fluorescent particle preparation process is complicated and the traditional polymer fluorescent sphere is micron or submicron grade in size and limited in application. The method comprises the following steps of: 1. refluxing by heating for preparing a seleno-sodium sulfate solution; 2. after mixing a seleno-sodium sulfate solution, a cadmium acetate solution, a sodium hydroxide solution, oleic acid and ethanol according to a certain proportion, carrying out heat reaction for preparing a cadmium selenide quantum dot; 3. extracting the quantum dot through styrene and preparing styrene even suspension; 4. carrying out emulsifying polymerization on the styrene suspension and reacting for preparing polystyrene nano fluorescent particle emulsion; and 5. adding salt into the styrene nano fluorescent particle emulsion, centrifuging, dispersing and storing to obtain the polystyrene fluorescent nano particle. The prepared polystyrene fluorescent nano particle can be applied to the fields of biomarkers, optical materials, cell imaging, and the like.
Description
Technical field: the preparation method who the present invention relates to a kind of polymer fluorescent nano particle.
Background technology
Quantum dot (QDs) is called nanocrystalline again, many modern luminescent materials and optics all are made of the semiconductor quantum structure, the quantum dot size that material forms is all approaching with the size of past dye molecule commonly used, thereby as fluorescence dye biomedical research is had very big purposes.On the difference of the luminous marker of living things system, quantum dot is owing to quantum-mechanical marvellous rule has significant dimensional effect, basically the light that is higher than specific thresholding all can absorb, quantum dot will absorb all photons that are higher than its band-gap energy, but the optical wavelength of being launched has size-dependent again very much, so, it is different that the nano semiconductor material of single kind just can produce an emission wavelength by dimensional change, the marker family that color is clearly demarcated, measure in point and have multiple advantage really, measuring in the benefit of a maximum is that abundant color is arranged, the complicacy of living things system often need be observed several components simultaneously, use the nanocrystals of different sizes to come the different biomolecules of mark, use single light source just can make the different particles can be by immediately monitoring.
The CdSe quantum dot is as a kind of crucial semiconductor nano, because photosensitive, the photoelectric characteristic of its ideal has obtained broad research, recently especially at biological monitoring and medical field.But because the toxicity and the fluorescence unstable of quantum dot, by shortcomings such as environment institute cancellation, the application of CdSe has been subjected to certain restriction to its fluorescent characteristic easily, and therefore, it is a kind of ideal means that quantum dot is coated.
Nanocrystalline coating at present mainly is divided into physisorphtion and monomer polymerization method. physical method be meant prepare nanocrystalline respectively and inert material after both are mixed, utilize physical actions such as Van der Waals force, hydrogen bond action, hydrophobic interaction and electrostatic interaction semiconductor nano to be adhered to or be assembled in the carrier inert material and obtain matrix material.Recently, people also begin to attempt being loaded with the monomer polymerization method preparation polymer fluorescent complex microsphere of semiconductor nano. and the method for bibliographical information is the synthetic nanocrystalline coating of CdSe of oil phase of modifying at trioctyl phosphine oxide (TOPO) mostly at present, but need modify quantum dot, complicated process of preparation, Gao etc. have attempted earlier electronegative nanocrystal being carried out phase transition with polymerisable emulsifying agent, carry out polymerization then and obtained micron-sized fluorescent polymer microballoon, Ford etc. utilize electrostatic interaction ethylene adsorption base benzene quaternary ammonium salt, then by method of emulsion polymerization clad nano crystalline substance, obtain the polymer fluorescent microspheres of submicron order, but the size of the microballoon that makes only limits to micron and submicron, makes their application in some aspects be subjected to certain restriction.
Summary of the invention
The present invention seeks to propose a kind of new method for preparing the polymer fluorescent particle, with solve present polymer fluorescent particle preparation complex process and at present the polymer fluorescent ball be of a size of micron or submicron order, the problem that application is restricted, and a kind of preparation method of polymer fluorescent nano particle is provided.
The preparation method of a kind of polymer fluorescent nano particle of the present invention carries out according to following steps: the deionized water that, adds selenium powder, 3.78g sodium sulphite anhydrous 99.3 and the 250ml of 1.975g in the there-necked flask of 500ml, under logical condition of nitrogen gas, be heated to 100 ℃～110 ℃ with oil bath, refluxed 2～4 hours, after stopping heating, under the condition of logical nitrogen, be cooled to room temperature, obtain water white sodium thiosulfate solution; Two, with mass percent concentration is that 6%～8% aqueous sodium hydroxide solution and mass percent concentration are 2%～3% the acetate dihydrate cadmium aqueous solution, add successively and be mixed with in dehydrated alcohol and the oleic Erlenmeyer flask, mixing liquid develops into white, in Erlenmeyer flask, add the water white transparency sodium thiosulfate solution that step 1 makes again, change liner teflon stainless steel tubular type reactor then over to, in temperature is under 40 ℃～155 ℃ conditions, reacted 1～17 hour, be cooled to room temperature, make the solid-liquid mixture that contains the CdSe quantum dot, wherein sodium hydroxide solution, the acetate dihydrate cadmium solution, dehydrated alcohol, the volume ratio of oleic acid and step 1 water white transparency sodium thiosulfate solution is 5: 5: 15: 4: 5; Three, add 50～100ml vinylbenzene in the solid-liquid mixture that contains the CdSe quantum dot that step 2 makes, shake up, pour pears type separating funnel then into and separate, discard subnatant, get upper strata styrene suspension liquid, wherein vinylbenzene is analytical reagent; Four, get styrene suspension liquid 50～60ml that step 3 makes and be distributed to that to contain mass percent concentration be that 0.1%～0.2% Sodium dodecylbenzene sulfonate and mass percent concentration are in the 200ml solution of 0.4%～0.5% sodium bicarbonate, under the nitrogen atmosphere, behind 250～350r/min stirring 40-55min, be warmed up to 60 ℃～70 ℃, and then to add 50ml, mass percent concentration be 0.7%～0.8% potassium persulfate solution, be warmed up to 70 ℃～90 ℃, reacted 6.5～9.5 hours, and obtained polystyrene fluorescent nano particles emulsion; Five, in the polystyrene fluorescent nano particles emulsion that step 4 obtains, add sodium-chlor to saturated, with the centrifugal 10～20min of 17995～18005r/min, get solid product, mass ratio according to solid product and water is 8～10: 1, solid product is distributed in the water, preserve, promptly obtain the polystyrene fluorescent nano particles.
Beneficial effect of the present invention is that the CdSe semiconductor nano of having realized preparation does not carry out any chemically modified or processing, with the poly styrene polymer is matrix, in polymkeric substance, introduce CdSe again, directly use method of emulsion polymerization, finish polystyrene to nanocrystalline coating, the preparation method is simple, economical, makes the polystyrene fluorescent particles of 20～100nm, can be applicable to fields such as biomarker, optical material, cell imaging.
Description of drawings
Fig. 1 is the quantum dot-based peak type variation diagram under fluorescence detector that embodiment one step 2 makes.
Fig. 2 is the polystyrene nanoparticle transmission photo of the coated quantum dots that makes of embodiment 12.
Fig. 3 is the photo of pipe/polyhenylethylene nano fluorescent particles emulsion under natural light that embodiment 12 makes.
Fig. 4 is the photo of pipe/polyhenylethylene nano fluorescent particles emulsion under ultraviolet lamp that embodiment 12 makes.
Embodiment
Embodiment one: a kind of preparation method of polymer fluorescent nano particle carries out according to following steps: the deionized water that, adds selenium powder, 3.78g sodium sulphite anhydrous 99.3 and the 250ml of 1.975g in the there-necked flask of 500ml, under logical condition of nitrogen gas, be heated to 100 ℃～110 ℃ with oil bath, refluxed 2～4 hours, after stopping heating, under the condition of logical nitrogen, be cooled to room temperature, obtain water white sodium thiosulfate solution; Two, with mass percent concentration is that 6%～8% sodium hydroxide solution and mass percent concentration are 2%～3% acetate dihydrate cadmium solution, add successively and be mixed with in dehydrated alcohol and the oleic Erlenmeyer flask, mixing liquid develops into white, in Erlenmeyer flask, add the water white transparency sodium thiosulfate solution that step 1 makes again, change liner teflon stainless steel tubular type reactor then over to, in temperature is under 40 ℃～155 ℃ conditions, reacted 1～17 hour, be cooled to room temperature, make the solid-liquid mixture that contains the CdSe quantum dot, wherein sodium hydroxide solution, the acetate dihydrate cadmium solution, dehydrated alcohol, the volume ratio of oleic acid and step 1 water white transparency sodium thiosulfate solution is 5: 5: 15: 4: 5; Three, add 50～100ml vinylbenzene in the solid-liquid mixture that contains the CdSe quantum dot that step 2 makes, shake up, pour pears type separating funnel then into and separate, discard subnatant, get upper strata styrene suspension liquid, wherein vinylbenzene is analytical reagent; Four, get styrene suspension liquid 50～60ml that step 3 makes and be distributed to that to contain mass percent concentration be that 0.1%～0.2% Sodium dodecylbenzene sulfonate and mass percent concentration are in the 200ml solution of 0.4%～0.5% sodium bicarbonate, under the nitrogen atmosphere, behind 250～350r/min stirring 40-55min, be warmed up to 60 ℃～70 ℃, and then to add 50ml, mass percent concentration be 0.7%～0.8% potassium persulfate solution, be warmed up to 70 ℃～90 ℃, reacted 6.5～9.5 hours, and obtained polystyrene fluorescent nano particles emulsion; Five, in the polystyrene fluorescent nano particles emulsion that step 4 obtains, add sodium-chlor to saturated, with the centrifugal 10～20min of 17995～18005r/min, get solid product, mass ratio according to solid product and water is 8～10: 1, solid product is distributed in the water, preserve, promptly obtain the polystyrene fluorescent nano particles.
The quantum dot color of step 2 preparation and differential responses time and temperature of reaction relation are as shown in table 1 below:
Table 1: quantum dot color and reaction times and temperature of reaction relation
| The quantum dot color | Temperature of reaction (℃) | Reaction times (hour) |
| Blue or green | 45 | 10 |
| Green | 100 | 10 |
| Yellow | 150 | 2 |
| Orange | 150 | 3 |
| Orange red | 150 | 10 |
| Red | 150 | 16 |
The quantum dot-based peak type variation diagram under fluorescence detector that the present embodiment step 2 makes has prepared the quantum dot of different fluorescence as shown in Figure 1 as seen from the figure.
Embodiment two: present embodiment and embodiment one difference are, the deionized water that in the there-necked flask of 500ml, adds selenium powder, 3.78g sodium sulphite anhydrous 99.3 and the 250ml of 1.975g in the step 1, under logical condition of nitrogen gas, begin to be heated to 102 ℃～108 ℃ with oil bath, refluxing stops heating after 2.5～3.5 hours, under the condition of logical nitrogen, be cooled to room temperature, obtain water white sodium thiosulfate solution, other step and parameter are identical with embodiment one.
Embodiment three: present embodiment and embodiment one or two differences are, the deionized water that in the there-necked flask of 500ml, adds selenium powder, 3.78g sodium sulphite anhydrous 99.3 and the 250ml of 1.975g in the step 1, under logical condition of nitrogen gas, begin to be heated to 105 ℃ with oil bath, refluxing stops heating after 3 hours, under the condition of logical nitrogen, be cooled to room temperature, obtain water white sodium thiosulfate solution, other step and parameter are identical with embodiment one or two.
Embodiment four: present embodiment and embodiment one to three difference are, in the step 2 be that 6.5% aqueous sodium hydroxide solution and mass concentration are 2.5% the acetate dihydrate cadmium aqueous solution with mass concentration, add successively and be mixed with in dehydrated alcohol and the oleic Erlenmeyer flask, liquid to be mixed develops into white, in Erlenmeyer flask, add the water white transparency sodium thiosulfate solution that step 1 makes again, change liner teflon stainless steel tubular type reactor over to, in temperature is under 150 ℃ of conditions, reacted 2 hours, make the solid-liquid mixture that contains the CdSe quantum dot, other step and parameter are identical with embodiment one to three.
Embodiment five: present embodiment and embodiment one to four difference are, in the step 2 be that 7% sodium hydroxide solution and mass concentration are 3% acetate dihydrate cadmium solution with mass concentration, add successively and be mixed with in dehydrated alcohol and the oleic Erlenmeyer flask, liquid to be mixed develops into white, in Erlenmeyer flask, add the water white transparency sodium thiosulfate solution that step 1 makes again, change liner teflon stainless steel tubular type reactor over to, in temperature is under 150 ℃ of conditions, reacted 3 hours, make the solid-liquid mixture that contains the CdSe quantum dot, other step and parameter are identical with embodiment one to four.
Embodiment six: present embodiment and embodiment one to five difference be, adds 60～90ml vinylbenzene in the step 3, and other step and parameter are identical with embodiment one to five.
Embodiment seven: present embodiment and embodiment one to six difference be, adds 75ml vinylbenzene in the step 3, and other step and parameter are identical with embodiment one to six.
Embodiment eight: present embodiment and embodiment one to seven difference are, the styrene suspension liquid 50ml that step 4 makes step 3 joins that to contain mass percent concentration be that 0.2% Sodium dodecylbenzene sulfonate and mass percent concentration are in the 200ml solution of 0.4% sodium bicarbonate, under the nitrogen atmosphere, behind 280r/min stirring 50min, be warmed up to 60 ℃, and then adding 50ml, mass percent concentration is 0.7% potassium persulfate solution, be warmed up to 75 ℃, reacted 9 hours, obtain polystyrene fluorescent nano particles emulsion, other step and parameter are identical with embodiment one to seven.
Embodiment nine: present embodiment and embodiment one to eight difference are, the styrene suspension liquid 55ml that step 4 makes step 3 joins that to contain mass percent concentration be that 0.25% Sodium dodecylbenzene sulfonate and mass percent concentration are in the 200ml solution of 0.45% sodium bicarbonate, under the nitrogen atmosphere, behind 300r/min stirring 45min, be warmed up to 65 ℃, and then adding 50ml, mass percent concentration is 0.75% potassium persulfate solution, be warmed up to 80 ℃, reacted 8 hours, obtain polystyrene fluorescent nano particles emulsion, other step and parameter are identical with embodiment one to eight.
Embodiment ten: present embodiment and embodiment one to nine difference are, the styrene suspension liquid 60ml that step 4 makes step 3 joins that to contain mass percent concentration be that 0.3% Sodium dodecylbenzene sulfonate and mass percent concentration are in the 200ml solution of 0.5% sodium bicarbonate, under the nitrogen atmosphere, behind 320r/min stirring 40min, be warmed up to 70 ℃, and then adding 50ml, mass percent concentration is 0.8% potassium persulfate solution, be warmed up to 85 ℃, reacted 7 hours, obtain polystyrene fluorescent nano particles emulsion, other step and parameter are identical with embodiment one to nine.
Embodiment 11: present embodiment and embodiment one to ten difference are, the polystyrene fluorescent nano particles emulsion that obtains to step 4 in the step 5 adds sodium-chlor to saturated, with the centrifugal 15min of 18000r/min, get solid product, mass ratio according to solid product and water is 9: 1, and solid product is distributed in the water, preserves, promptly obtain the polystyrene fluorescent nano particles, other step and parameter are identical with embodiment one to ten.
Embodiment 12: a kind of preparation method of polymer fluorescent nano particle carries out according to following steps: the deionized water that, adds selenium powder, 3.78g sodium sulphite anhydrous 99.3 and the 250ml of 1.975g in the there-necked flask of 500ml, under logical condition of nitrogen gas, be heated to 105 ℃ with oil bath, refluxed 3 hours, after stopping heating, under the condition of logical nitrogen, be cooled to room temperature, obtain water white sodium thiosulfate solution; Two, with mass percent concentration is that 7% sodium hydroxide solution and mass percent concentration are 3% acetate dihydrate cadmium solution, add successively and be mixed with in dehydrated alcohol and the oleic Erlenmeyer flask, mixing liquid develops into white, in Erlenmeyer flask, add the water white transparency sodium thiosulfate solution that step 1 makes again, change liner teflon stainless steel tubular type reactor then over to, in temperature is under 150 ℃ of conditions, reacted 3 hours, be cooled to room temperature, make the solid-liquid mixture that contains the CdSe quantum dot, wherein sodium hydroxide solution, the acetate dihydrate cadmium solution, dehydrated alcohol, the volume ratio of oleic acid and step 1 water white transparency sodium thiosulfate solution is 5: 5: 15: 4: 5; Three, add 50ml vinylbenzene in the solid-liquid mixture that contains the CdSe quantum dot that step 2 makes, shake up, pour pears type separating funnel then into and separate, discard subnatant, get upper strata styrene suspension liquid, wherein vinylbenzene is analytical reagent; Four, get styrene suspension liquid 55ml that step 3 makes and be distributed to that to contain mass percent concentration be that 0.2% Sodium dodecylbenzene sulfonate and mass percent concentration are in the 200ml solution of 0.5% sodium bicarbonate, under the nitrogen atmosphere, behind 320r/min stirring 40min, be warmed up to 60 ℃, and then to add 50ml, mass percent concentration be 0.7% potassium persulfate solution, be warmed up to 80 ℃, reacted 8 hours, obtain polystyrene fluorescent nano particles emulsion; Five, in the polystyrene fluorescent nano particles emulsion that step 4 obtains, add saturated sodium-chloride,, get solid product with the centrifugal 15min of 18000r/min, mass ratio according to solid product and water is 9: 1, solid product is distributed in the water, preserves, promptly obtain the polystyrene fluorescent nano particles.
The polystyrene nanoparticle transmission photo of the coated quantum dots that is made by present embodiment as shown in Figure 2, the photo of pipe/polyhenylethylene nano fluorescent particles emulsion under natural light and UV-light that is made by present embodiment as shown in Figure 3 and Figure 4, Fig. 4 has reflected the successful coated quantum dots of nanoparticle of preparation and under UV-irradiation fluorescence has been arranged that Fig. 3 has reflected the successful coated quantum dots of nanoparticle of preparation but do not have fluorescence under natural light irradiation.
Claims (9)
1. the preparation method of a polymer fluorescent nano particle, it is characterized in that this method is to carry out according to following steps: the deionized water that, in the there-necked flask of 500ml, adds selenium powder, 3.78g sodium sulphite anhydrous 99.3 and the 250ml of 1.975g, under logical condition of nitrogen gas, be heated to 100 ℃～110 ℃ with oil bath, refluxed 2～4 hours, after stopping to heat, under the condition of logical nitrogen, be cooled to room temperature, obtain water white sodium thiosulfate solution; Two, with mass percent concentration is that 6%～8% sodium hydroxide solution and mass percent concentration are 2%～3% acetate dihydrate cadmium solution, add successively and be mixed with in dehydrated alcohol and the oleic Erlenmeyer flask, mixing liquid develops into white, in Erlenmeyer flask, add the water white transparency sodium thiosulfate solution that step 1 makes again, change liner teflon stainless steel tubular type reactor then over to, in temperature is under 40 ℃～155 ℃ conditions, reacted 1～17 hour, be cooled to room temperature, make the solid-liquid mixture that contains the CdSe quantum dot, wherein sodium hydroxide solution, the acetate dihydrate cadmium solution, dehydrated alcohol, the volume ratio of oleic acid and step 1 water white transparency sodium thiosulfate solution is 5: 5: 15: 4: 5; Three, add 50～100ml vinylbenzene in the solid-liquid mixture that contains the CdSe quantum dot that step 2 makes, shake up, pour pears type separating funnel then into and separate, discard subnatant, get upper strata styrene suspension liquid, wherein vinylbenzene is analytical reagent; Four, get styrene suspension liquid 50～60ml that step 3 makes and be distributed to that to contain mass percent concentration be that 0.1%～0.2% Sodium dodecylbenzene sulfonate and mass percent concentration are in the 200ml solution of 0.4%～0.5% sodium bicarbonate, under the nitrogen atmosphere, behind 250～350r/min stirring, 40～55min, be warmed up to 60 ℃～70 ℃, and then to add 50ml, mass percent concentration be 0.7%～0.8% potassium persulfate solution, be warmed up to 70 ℃～90 ℃, reacted 6.5～9.5 hours, and obtained polystyrene fluorescent nano particles emulsion; Five, in the polystyrene fluorescent nano particles emulsion that step 4 obtains, add sodium-chlor to saturated, with the centrifugal 10～20min of 17995～18005r/min, get solid product, mass ratio according to solid product and water is 8～10: 1, solid product is distributed in the water, preserve, promptly obtain the polystyrene fluorescent nano particles.
2. according to the preparation method of the described a kind of polymer fluorescent nano particle of claim 1, it is characterized in that being heated to 102 ℃～108 ℃ with oil bath in the step 1, reflux after 2.5～3.5 hours, stop heating.
3. according to the preparation method of the described a kind of polymer fluorescent nano particle of claim 1, it is characterized in that being heated to 105 ℃ with oil bath in the step 1, reflux after 3 hours, stop heating.
4. according to the preparation method of the described a kind of polymer fluorescent nano particle of claim 1, it is characterized in that in the step 2 with mass percent concentration being that 7% aqueous sodium hydroxide solution and mass percent concentration are 2.5% the acetate dihydrate cadmium aqueous solution, add successively and be mixed with in dehydrated alcohol and the oleic Erlenmeyer flask, liquid to be mixed develops into white, in Erlenmeyer flask, add the water white transparency sodium thiosulfate solution that step 1 makes again, change liner teflon stainless steel tubular type reactor over to, in temperature is under 150 ℃ of conditions, reacted 3 hours, be cooled to room temperature, make the solid-liquid mixture that contains the CdSe quantum dot.
5. according to the preparation method of the described a kind of polymer fluorescent nano particle of claim 1, it is characterized in that adding in the step 3 60～90ml vinylbenzene.
6. according to the preparation method of the described a kind of polymer fluorescent nano particle of claim 1, it is characterized in that adding in the step 3 75ml vinylbenzene.
7. according to the preparation method of the described a kind of polymer fluorescent nano particle of claim 1, it is characterized in that styrene suspension liquid 55ml that step 4 makes step 3 joins that to contain mass percent concentration be that 0.15% Sodium dodecylbenzene sulfonate and mass percent concentration are in the 200ml solution of 0.45% sodium bicarbonate, under the nitrogen atmosphere, behind 300r/min stirring 45min, be warmed up to 65 ℃, and then adding 50ml, mass percent concentration is 0.75% potassium persulfate solution, be warmed up to 80 ℃, reacted 8 hours, and obtained polystyrene fluorescent nano particles emulsion.
8. according to the preparation method of the described a kind of polymer fluorescent nano particle of claim 1, it is characterized in that the styrene suspension liquid 50ml that in the step 4 step 3 is made joins that to contain mass percent concentration be that 0.2% Sodium dodecylbenzene sulfonate and mass percent concentration are in the 200ml solution of 0.4% sodium bicarbonate, under the nitrogen atmosphere, behind 280r/min stirring 50min, be warmed up to 60 ℃, and then adding 50ml, mass percent concentration is 0.7% potassium persulfate solution, be warmed up to 75 ℃, reacted 9 hours, and obtained polystyrene fluorescent nano particles emulsion.
9. according to the preparation method of the described a kind of polymer fluorescent nano particle of claim 1, it is characterized in that in the polystyrene fluorescent nano particles emulsion that step 4 obtains, adding in the step 5 sodium-chlor to saturated, with 18000r/min centrifugation 15min, obtain solid product, mass ratio according to solid product and water is 9: 1, solid product is distributed in the water, preserves, promptly obtain the polystyrene fluorescent nano particles.
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