CN102060948B - 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 up 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 optical dye biomedical research is had very big purposes.Say from the difference of the luminous marker of living things system; Quantum dot is owing to quantum-mechanical marvellous rule has significant dimensional effect, and the light that is higher than specific thresholding basically all can absorb, and 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 the nano semiconductor material of single kind just can produce an emission wavelength affinity tag family different, that color is clearly demarcated by dimensional change, 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 kinds of components simultaneously, uses the nanocrystals of different sizes to come the different biomolecules of mark, uses 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 received 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. and physical method after being meant and preparing nanocrystalline and inert material respectively mixes both, utilizes 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 obtains 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 to 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, and are brilliant through the method for emulsion polymerization clad nano then, 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 receive 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, 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 heating; Under the condition of logical nitrogen, be cooled to room temperature, obtain water white sodium thiosulfate solution; Two, be that 6%～8% aqueous sodium hydroxide solution and mass percent concentration are 2%～3% the acetate dihydrate cadmium aqueous solution with mass percent concentration; Add successively and be mixed with in absolute ethyl alcohol and the oleic Erlenmeyer flask; Mixing liquid develops into white; In Erlenmeyer flask, adding the water white transparency sodium thiosulfate solution that step 1 makes again, change liner ZX 21 stainless steel tubular type reaction kettle then over to, is under 40 ℃～155 ℃ conditions in temperature; Reacted 1～17 hour; Be cooled to room temperature, make the solid-liquid mixture that contains the CdSe quantum dot, wherein the volume ratio of sodium hydroxide solution, acetate dihydrate cadmium solution, absolute ethyl alcohol, oleic acid and step 1 water white transparency sodium thiosulfate solution is 5: 5: 15: 4: 5; Three, in the solid-liquid mixture that contains the CdSe quantum dot that step 2 makes, add 50～100ml vinylbenzene, shake up, pour pears type separating funnel then into and separate, discard subnatant, get upper strata styrene suspension liquid, wherein vinylbenzene is AR; 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% X 2073 and mass percent concentration are in the 200ml solution of 0.4%～0.5% sodium hydrogencarbonate; Under the nitrogen atmosphere; Behind 250～350r/min stirring 40-55min; Be warmed up to 60 ℃～70 ℃, and then to add the 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 PS fluorescent nano particles emulsion; Five, in the PS fluorescent nano particles emulsion that step 4 obtains, add sodium-chlor to saturated; With the centrifugal 10～20min of 17995～18005r/min; Solid product, be 8～10: 1 according to the mass ratio of solid product and water, solid product is distributed in the water; Preserve, promptly obtain the PS 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, introduces CdSe again, directly uses method of emulsion polymerization; Accomplish PS to nanocrystalline coating; The preparation method is simple, economical, makes the PS 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 uv 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, 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 heating; Under the condition of logical nitrogen, be cooled to room temperature, obtain water white sodium thiosulfate solution; Two, be that 6%～8% sodium hydroxide solution and mass percent concentration are 2%～3% acetate dihydrate cadmium solution with mass percent concentration; Add successively and be mixed with in absolute ethyl alcohol and the oleic Erlenmeyer flask; Mixing liquid develops into white; In Erlenmeyer flask, adding the water white transparency sodium thiosulfate solution that step 1 makes again, change liner ZX 21 stainless steel tubular type reaction kettle then over to, is under 40 ℃～155 ℃ conditions in temperature; Reacted 1～17 hour; Be cooled to room temperature, make the solid-liquid mixture that contains the CdSe quantum dot, wherein the volume ratio of sodium hydroxide solution, acetate dihydrate cadmium solution, absolute ethyl alcohol, oleic acid and step 1 water white transparency sodium thiosulfate solution is 5: 5: 15: 4: 5; Three, in the solid-liquid mixture that contains the CdSe quantum dot that step 2 makes, add 50～100ml vinylbenzene, shake up, pour pears type separating funnel then into and separate, discard subnatant, get upper strata styrene suspension liquid, wherein vinylbenzene is AR; 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% X 2073 and mass percent concentration are in the 200ml solution of 0.4%～0.5% sodium hydrogencarbonate; Under the nitrogen atmosphere; Behind 250～350r/min stirring 40-55min; Be warmed up to 60 ℃～70 ℃, and then to add the 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 PS fluorescent nano particles emulsion; Five, in the PS fluorescent nano particles emulsion that step 4 obtains, add sodium-chlor to saturated; With the centrifugal 10～20min of 17995～18005r/min; Solid product, be 8～10: 1 according to the mass ratio of solid product and water, solid product is distributed in the water; Preserve, promptly obtain the PS 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) |
| Celadon | 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 this embodiment step 2 makes is as shown in Figure 1, can know the quantum dot that has prepared different fluorescence by figure.
Embodiment two: this embodiment is in the there-necked flask of 500ml, to add the deionized water of 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 with embodiment one difference; 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: this embodiment is in the there-necked flask of 500ml, to add the deionized water of 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 with embodiment one or two differences; 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: this embodiment with embodiment one to three difference is; Be that 6.5% aqueous sodium hydroxide solution and mass concentration are 2.5% the acetate dihydrate cadmium aqueous solution with mass concentration in the step 2, add successively and be mixed with in absolute ethyl alcohol and the oleic Erlenmeyer flask that liquid to be mixed develops into white; In Erlenmeyer flask, add the water white transparency sodium thiosulfate solution that step 1 makes again; Changing liner ZX 21 stainless steel tubular type reaction kettle over to, is under 150 ℃ of conditions in temperature, reacts 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: this embodiment with embodiment one to four difference is; Be that 7% sodium hydroxide solution and mass concentration are 3% acetate dihydrate cadmium solution with mass concentration in the step 2, add successively and be mixed with in absolute ethyl alcohol and the oleic Erlenmeyer flask that liquid to be mixed develops into white; In Erlenmeyer flask, add the water white transparency sodium thiosulfate solution that step 1 makes again; Changing liner ZX 21 stainless steel tubular type reaction kettle over to, is under 150 ℃ of conditions in temperature, reacts 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: this 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: this embodiment and embodiment one to six difference be, adds 75ml vinylbenzene in the step 3, and other step and parameter and embodiment one to six phase are same.
Embodiment eight: this embodiment with embodiment one to seven difference is; The styrene suspension liquid 50ml that step 4 makes step 3 joins that to contain mass percent concentration be that 0.2% X 2073 and mass percent concentration are in the 200ml solution of 0.4% sodium hydrogencarbonate, under the nitrogen atmosphere, stir 50min with 280r/min after; Be warmed up to 60 ℃; And then to add the 50ml mass percent concentration be 0.7% potassium persulfate solution, is warmed up to 75 ℃, reacted 9 hours; Obtain PS fluorescent nano particles emulsion, other step and parameter are identical with embodiment one to seven.
Embodiment nine: this embodiment with embodiment one to eight difference is; The styrene suspension liquid 55ml that step 4 makes step 3 joins that to contain mass percent concentration be that 0.25% X 2073 and mass percent concentration are in the 200ml solution of 0.45% sodium hydrogencarbonate, under the nitrogen atmosphere, stir 45min with 300r/min after; Be warmed up to 65 ℃; And then to add the 50ml mass percent concentration be 0.75% potassium persulfate solution, is warmed up to 80 ℃, reacted 8 hours; Obtain PS fluorescent nano particles emulsion, other step and parameter are identical with embodiment one to eight.
Embodiment ten: this embodiment with embodiment one to nine difference is; The styrene suspension liquid 60ml that step 4 makes step 3 joins that to contain mass percent concentration be that 0.3% X 2073 and mass percent concentration are in the 200ml solution of 0.5% sodium hydrogencarbonate, under the nitrogen atmosphere, stir 40min with 320r/min after; Be warmed up to 70 ℃; And then to add the 50ml mass percent concentration be 0.8% potassium persulfate solution, is warmed up to 85 ℃, reacted 7 hours; Obtain PS fluorescent nano particles emulsion, other step and parameter are identical with embodiment one to nine.
Embodiment 11: this embodiment is that the PS 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 with embodiment one to ten difference; 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 PS 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, 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 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, be that 7% sodium hydroxide solution and mass percent concentration are 3% acetate dihydrate cadmium solution with mass percent concentration; Adding is mixed with in absolute ethyl alcohol and the oleic Erlenmeyer flask successively, and mixing liquid develops into white, in Erlenmeyer flask, adds the water white transparency sodium thiosulfate solution that step 1 makes again; Change liner ZX 21 stainless steel tubular type reaction kettle then over to; In temperature is under 150 ℃ of conditions, reacts 3 hours, is cooled to room temperature; Make the solid-liquid mixture that contains the CdSe quantum dot, wherein the volume ratio of sodium hydroxide solution, acetate dihydrate cadmium solution, absolute ethyl alcohol, oleic acid and step 1 water white transparency sodium thiosulfate solution is 5: 5: 15: 4: 5; Three, in the solid-liquid mixture that contains the CdSe quantum dot that step 2 makes, add 50ml vinylbenzene, shake up, pour pears type separating funnel then into and separate, discard subnatant, get upper strata styrene suspension liquid, wherein vinylbenzene is AR; Four, get styrene suspension liquid 55ml that step 3 makes and be distributed to that to contain mass percent concentration be that 0.2% X 2073 and mass percent concentration are in the 200ml solution of 0.5% sodium hydrogencarbonate; Under the nitrogen atmosphere, behind 320r/min stirring 40min, be warmed up to 60 ℃; And then adding 50ml mass percent concentration is 0.7% potassium persulfate solution; Be warmed up to 80 ℃, reacted 8 hours, obtain PS fluorescent nano particles emulsion; Five, in the PS 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 PS fluorescent nano particles.
The polystyrene nanoparticle transmission photo of the coated quantum dots that is made by this embodiment is as shown in Figure 2; Pipe/polyhenylethylene nano fluorescent particles emulsion photo such as the Fig. 3 and shown in Figure 4 under natural light and UV-light that makes by this embodiment; Fig. 4 reflected the successful coated quantum dots of nanoparticle of preparation and under UV-irradiation, fluorescence arranged, Fig. 3 reflected preparation nanoparticle successful coated quantum dots but under natural light irradiation no fluorescence.
Claims (9)
1. the preparation method of a polymer fluorescent nano particle is characterized in that this method is to carry out according to following steps: one, in the there-necked flask of 500ml, add the deionized water of 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, be that 6%～8% sodium hydroxide solution and mass percent concentration are 2%～3% acetate dihydrate cadmium solution with mass percent concentration; Add successively and be mixed with in absolute ethyl alcohol and the oleic Erlenmeyer flask; Mixing liquid develops into white; In Erlenmeyer flask, adding the water white transparency sodium thiosulfate solution that step 1 makes again, change liner ZX 21 stainless steel tubular type reaction kettle then over to, is under 40 ℃～155 ℃ conditions in temperature; Reacted 1～17 hour; Be cooled to room temperature, make the solid-liquid mixture that contains the CdSe quantum dot, wherein the volume ratio of sodium hydroxide solution, acetate dihydrate cadmium solution, absolute ethyl alcohol, oleic acid and step 1 water white transparency sodium thiosulfate solution is 5: 5: 15: 4: 5; Three, in the solid-liquid mixture that contains the CdSe quantum dot that step 2 makes, add 50～100ml vinylbenzene, shake up, pour pears type separating funnel then into and separate, discard subnatant, get upper strata styrene suspension liquid, wherein vinylbenzene is AR; 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% X 2073 and mass percent concentration are in the 200ml solution of 0.4%～0.5% sodium hydrogencarbonate; Under the nitrogen atmosphere; Behind 250～350r/min stirring, 40～55min; Be warmed up to 60 ℃～70 ℃, and then to add the 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 PS fluorescent nano particles emulsion; Five, in the PS fluorescent nano particles emulsion that step 4 obtains, add sodium-chlor to saturated; With the centrifugal 10～20min of 17995～18005r/min; Solid product, be 8～10: 1 according to the mass ratio of solid product and water, solid product is distributed in the water; Preserve, promptly obtain the PS fluorescent nano particles.
2. according to the preparation method of the said 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 said 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 said 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 absolute ethyl alcohol and the oleic Erlenmeyer flask that liquid to be mixed develops into white; In Erlenmeyer flask, add the water white transparency sodium thiosulfate solution that step 1 makes again; Changing liner ZX 21 stainless steel tubular type reaction kettle over to, is under 150 ℃ of conditions in temperature, reacts 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 said 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 said 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 said 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% X 2073 and mass percent concentration are in the 200ml solution of 0.45% sodium hydrogencarbonate; 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 PS fluorescent nano particles emulsion.
8. according to the preparation method of the said 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% X 2073 and mass percent concentration are in the 200ml solution of 0.4% sodium hydrogencarbonate; 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 PS fluorescent nano particles emulsion.
9. according to the preparation method of the said a kind of polymer fluorescent nano particle of claim 1; It is characterized in that in the PS fluorescent nano particles emulsion that step 4 obtains, adding in the step 5 sodium-chlor to saturated,, obtain solid product with 18000r/min centrifugation 15min; Mass ratio according to solid product and water is 9: 1; Solid product is distributed in the water, preserves, promptly obtain the PS fluorescent nano particles.
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| CN111346674A (en) * | 2018-12-24 | 2020-06-30 | 上海萃励电子科技有限公司 | Synthesis method of CdSe-loaded poly-1, 4-naphthalene diamine |
| CN116478694A (en) * | 2023-04-23 | 2023-07-25 | 天津大学 | Preparation and array method of polystyrene encapsulated nanocrystalline composite luminescent material |
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