CN106084160A - A kind of self-luminous fluorescent microsphere and preparation method thereof - Google Patents
A kind of self-luminous fluorescent microsphere and preparation method thereof Download PDFInfo
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- CN106084160A CN106084160A CN201610403025.5A CN201610403025A CN106084160A CN 106084160 A CN106084160 A CN 106084160A CN 201610403025 A CN201610403025 A CN 201610403025A CN 106084160 A CN106084160 A CN 106084160A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/10—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenol
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- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
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Abstract
The invention discloses a kind of self-luminous fluorescent microsphere and preparation method thereof, belong to technical field of function materials.Using modified St ber method, phenol, formaldehyde or glutaraldehyde have the fluorescent microsphere of spontaneous nature by sol gel course of reaction, preparation, its fluorescence radiation is lasting, is difficult to quencher.Preparation method used by the present invention is easy, need not add any surfactant and emulsifying agent, only need to by phenol and formaldehyde (or glutaraldehyde) in water under ammonia-catalyzed, at relatively low temperature, (reaction temperature is not higher than 95oC) carry out reacting.The fluorescent microsphere size tunable for preparing, being evenly distributed, single dispersing, have the characteristic of autofluorescence, it is luminous persistently, is difficult to quencher.The fluorescent microsphere of the present invention can be stably dispersed in water, ethanol, acetone, nitrogen, in nitrogen dimethylformamide, acetonitrile equal solvent, has wide practical use in fields such as fluorescent probe microsphere, fluidic cell bioanalysiss.
Description
Technical field
The invention belongs to technical field of function materials, be particularly related to a kind of self-luminous fluorescent microsphere and preparation method thereof.
Background technology
Polymer fluorescent microspheres refers to that diameter is at nanometer to micron order the polymer microballoon that is loaded with fluorescent material.Outside it
Shape can be arbitrary shape, the most spherical.Wherein, fluorescent microsphere is with its stable morphosis and stable and efficient luminous effect
Rate, demonstrates huge answering in labelling, spike, detection, standard, immobilized enzyme, the immunity field such as medical science, high-flux medicaments sifting
Use potentiality.Therefore, in recent years about the research of polymer fluorescent microspheres high performance increasingly by domestic and international scientist's
Pay close attention to, it has also become the focus of this area research and difficult point.
Polymer fluorescent microspheres passes through emulsion polymerization, precipitation polymerization, seeding polymerization, dispersin polymerization etc. particle diameter 0.1 micron
Preferable single dispersibility can be obtained to 100 microns to prepare, and have preferable repeatability.The most glimmering to macromolecule
The research of light microsphere has a lot.Wherein it is mainly polystyrene microsphere, polymethyl methacrylate (PMMA) microsphere, melamine resin
(MF) microsphere.These several fluorescent microspheres can reach good size controlling and the highest monodispersity.Although PS fluorescence is micro-
Ball, PMMA fluorescent microsphere, MF fluorescent microsphere are all successfully prepared, no matter for development or the need in market of each subject
Asking, the quality and quantity of fluorescent microsphere all has great prospects for development.And these several microspheres above itself do not have spontaneous
The advantage of fluorescence, needs bag to carry dyestuff or quantum dot just can inspire fluorescence, and this most greatly adds cost.Further, bag
As time goes on the dyestuff carried or quantum dot can occur to run off or cancellation, and this most greatly have impact on sending out of microsphere
Optical property and service life.
The present invention utilizes the St ber method of modification, phenol, formaldehyde or glutaraldehyde pass through sol gel course of reaction, system
Getting everything ready the fluorescent microsphere of spontaneous nature, its fluorescence radiation is lasting, is difficult to quencher.Compared with other preparation method, institute of the present invention
By method, there is the simple advantage of course of reaction, need not any emulsifying agent and surfactant, only need to by molten to phenol and formaldehyde (or
Glutaraldehyde) in water under ammonia-catalyzed, at relatively low temperature, (reaction temperature is not higher than 95oC) carry out reacting.And the party
The microsphere that method obtains has following advantage relative to additive method, and particle diameter is micro-meter scale, is evenly distributed, and balling-up is good,
Applicable flow cytometric analysis, and there is the characteristic of autofluorescence, it is luminous persistently, is difficult to quencher.
Summary of the invention
It is an object of the invention to provide a kind of self-luminous fluorescent microsphere and preparation method thereof, the phenol prepared in the present invention
Urea formaldehyde fluorescent microsphere has that compound with regular structure, grain size be controlled, single dispersing, have the characteristic of autofluorescence, and it is luminous persistently,
It is difficult to quencher.There is the hydrophile function groups such as substantial amounts of phenolic hydroxyl group, methylol in this self-luminous fluorescent microsphere, phenyl ring has thin simultaneously
Aqueous, therefore has amphipathic, and microsphere can be stably dispersed in water, ethanol, acetone, nitrogen, and nitrogen dimethylformamide, acetonitrile etc. are molten
In agent, there is the widest application prospect in fields such as fluorescent probe microsphere, fluidic cell bioanalysiss.
The present invention is achieved by the following technical solutions:
This fluorescent microsphere is to utilize modified St ber method, phenol, formaldehyde or glutaraldehyde pass through sol gel course of reaction,
Prepare.Preparation process is as follows: by phenol, formaldehyde or glutaraldehyde by the proportioning mix homogeneously set, then regulation system is anti-
Answer temperature, be incubated the regular hour, add a certain amount of ammonia as catalyst initiation reaction.The solution that will have reacted, is carried out
Centrifugal, respectively with distilled water and ethanol purge, then it is dried in vacuum drying oven.
Specifically comprise the following steps that
(1) by 1.0 g phenol, 1.5 mL-6 mL formaldehyde or glutaraldehyde and 40 mL distilled water join in there-necked flask, ultrasonic
After mix homogeneously, it is stirred with 250 r/min, is warming up to 50-95oC, is incubated 30 min.
(2) in the pre-reaction solution that step (1) obtains, add 10 L-10 mL ammonia, after reaction 2-24 h, add
1 mol/L hydrochloric acid solution, regulation pH is to neutral, and reaction system is cooled to room temperature.
(3) product of step (2) is separated by centrifugal method, clean with distilled water, ethanol, distilled water the most respectively
Three times, in vacuum drying oven, finally it is dried 4 h.
The remarkable advantage of the present invention: method therefor of the present invention has the simple advantage of course of reaction, need not add any breast
Agent and surfactant, only need to by molten to phenol and formaldehyde (or glutaraldehyde) in water under ammonia-catalyzed, in (the reaction of relatively low temperature
Temperature is not higher than 95oC) carry out reacting.The phenolic resin fluorescent microsphere prepared in the present invention have compound with regular structure,
Grain size is controlled at 0.6 m-4.5 m, single dispersing, have the characteristic of autofluorescence, and it is luminous persistently, is difficult to quencher.Should
There is the hydrophile function groups such as substantial amounts of phenolic hydroxyl group, methylol in self-luminous fluorescent microsphere, phenyl ring has hydrophobicity simultaneously, therefore has
Having amphipathic, microsphere can be stably dispersed in water, ethanol, acetone, nitrogen, in nitrogen dimethylformamide, acetonitrile equal solvent, at fluorescence
There is the widest application prospect in the fields such as probe microsphere, fluidic cell bioanalysis.
Accompanying drawing explanation
Fig. 1-a is the scanning electron microscope (SEM) photograph of self-luminous fluorescent microsphere prepared by embodiment 1 reaction condition；
Fig. 1-b is the scanning electron microscope (SEM) photograph of self-luminous fluorescent microsphere prepared by embodiment 2 reaction condition；
Fig. 1-c is the scanning electron microscope (SEM) photograph of self-luminous fluorescent microsphere prepared by embodiment 3 reaction condition；
Fig. 1-d is the scanning electron microscope (SEM) photograph of self-luminous fluorescent microsphere prepared by embodiment 4 reaction condition；
Fig. 1-e is the scanning electron microscope (SEM) photograph of self-luminous fluorescent microsphere prepared by embodiment 5 reaction condition；
Fig. 1-f is the scanning electron microscope (SEM) photograph of self-luminous fluorescent microsphere prepared by embodiment 6 reaction condition.
Fig. 2-a is the microsphere fluorescence microphotograph and fluorescence emission spectrogram prepared for cross-linking agent with formaldehyde.
Fig. 2-b is the microsphere fluorescence microphotograph and fluorescence emission spectrogram prepared with glutaraldehyde as cross linker.
Fig. 2-c is microsphere fluorescence microphotograph and the fluorescence emission spectrogram that self-luminous is combined preparation with FITC.
Fig. 2 (a)-(c) illustrates, self-luminous fluorescent microsphere prepared by this invention both can be the most permissible with Single wavelength fluorescent emission
Multi-wavelength emission, it is also possible to be combined with other fluorescent probes and overlapping wavelengths interference does not occur to launch, this self-luminous microsphere is described
It is widely applied prospect in fields such as fluorescence-encoded micro-beads high flux biological detection, fluidic cell bioanalysiss.
Detailed description of the invention
(1) by 1.0 g phenol, 1.5 mL-6 mL formaldehyde or glutaraldehyde and 40 mL distilled water join in there-necked flask,
After ultrasonic mix homogeneously, it is stirred with 250 r/min, is warming up to 50-95oC, is incubated 30 min.
(2) in the pre-reaction solution that step (1) obtains, add 10 L-10 mL ammonia, after reaction 2-24 h, add
1 mol/L hydrochloric acid solution, regulation pH is to neutral, and reaction system is cooled to room temperature.
(3) product of step (2) is separated by centrifugal method, clean with distilled water, ethanol, distilled water the most respectively
Three times, in vacuum drying oven, finally it is dried 4 h.
Embodiment 1:
(1) by 1.0 g phenol, 5 mL formaldehyde and 40 mL distilled water join in there-necked flask, after ultrasonic mix homogeneously, with 250
R/min is stirred, and is warming up to 80oC, is incubated 30 min.
(2) in the pre-reaction solution that step (1) obtains, add 4 mL ammonia, after reacting 24 h, add 1 mol/L hydrochloric acid
Solution, regulation pH is to neutral, and reaction system is cooled to room temperature.
(3) it is centrifuged separating by 5000 r/min by the product of step (2), the most respectively with distilled water, ethanol, steaming
Distilled water is cleaned three times, is finally dried 4 h in vacuum drying oven.
The particle diameter of the self-luminous fluorescent microsphere prepared is 4.5 m.
Embodiment 2:
(1) by 1.0 g phenol, 5 mL formaldehyde and 40 mL distilled water join in there-necked flask, after ultrasonic mix homogeneously, with 250
R/min is stirred, and is warming up to 80oC, is incubated 30 min.
(2) in the pre-reaction solution that step (1) obtains, add 6 mL ammonia, after reacting 24 h, add 1 mol/L hydrochloric acid
Solution, regulation pH is to neutral, and reaction system is cooled to room temperature.
(3) it is centrifuged separating by 5000 r/min by the product of step (2), the most respectively with distilled water, ethanol, steaming
Distilled water is cleaned three times, is finally dried 4 h in vacuum drying oven.
The particle diameter of the self-luminous fluorescent microsphere prepared is 3 m.
Embodiment 3:
(1) by 1.0 g phenol, 5 mL formaldehyde and 40 mL distilled water join in there-necked flask, after ultrasonic mix homogeneously, with 250
R/min is stirred, and is warming up to 80oC, is incubated 30 min.
(2) in the pre-reaction solution that step (1) obtains, add 8 mL ammonia, after reacting 24 h, add 1 mol/L hydrochloric acid
Solution, regulation pH is to neutral, and reaction system is cooled to room temperature.
(3) it is centrifuged separating by 5000 r/min by the product of step (2), the most respectively with distilled water, ethanol, steaming
Distilled water is cleaned three times, is finally dried 4 h in vacuum drying oven.
The particle diameter of the self-luminous fluorescent microsphere prepared is 2.5 m.
Embodiment 4:
(1) by 1.0 g phenol, 2 mL glutaraldehydes and 40 mL distilled water join in there-necked flask, after ultrasonic mix homogeneously, with
250 r/min are stirred, and are warming up to 50oC, is incubated 30 min.
(2) in the pre-reaction solution that step (1) obtains, add 40 L ammonia, after reacting 24 h, add 1 mol/L salt
Acid solution, regulation pH is to neutral, and reaction system is cooled to room temperature.
(3) it is centrifuged separating by 5000 r/min by the product of step (2), the most respectively with distilled water, ethanol, steaming
Distilled water is cleaned three times, is finally dried 4 h in vacuum drying oven.
The particle diameter of the self-luminous fluorescent microsphere prepared is 1.5 m.
Embodiment 5:
(1) by 1.0 g phenol, 2 mL glutaraldehyde solutions and 40 mL distilled water join in there-necked flask, ultrasonic mix homogeneously
After, it is stirred with 250 r/min, is warming up to 60oC, is incubated 30.
(2) in the pre-reaction solution that step (1) obtains, add 60 L ammonia, after μ reacts 24 h, add 1 mol/L salt
Acid solution, regulation pH is to neutral, and reaction system is cooled to room temperature.
(3) it is centrifuged separating by 5000 r/min by the product of step (2), the most respectively with distilled water, ethanol, steaming
Distilled water is cleaned three times, is finally dried 4 h in vacuum drying oven.
The particle diameter of the self-luminous fluorescent microsphere prepared is 1 m.
Embodiment 6:
(1) by 1.0 g phenol, 2 mL glutaraldehydes and 40 mL distilled water join in there-necked flask, after ultrasonic mix homogeneously, with
250 r/min are stirred, and are warming up to 90oC, is incubated 30 min.
(2) in the pre-reaction solution that step (1) obtains, add 100 L ammonia, after reacting 24 h, add 1 mol/L salt
Acid solution, regulation pH is to neutral, and reaction system is cooled to room temperature.
(3) it is centrifuged separating by 5000 r/min by the product of step (2), the most respectively with distilled water, ethanol, steaming
Distilled water is cleaned three times, is finally dried 4 h in vacuum drying oven.
The particle diameter of the self-luminous fluorescent microsphere prepared is 0.6 m.
Embodiment 7: self-luminous is combined with other fluorescent probe can prepare multiple colour light emitting microsphere
(1) by 1.0 g phenol, 5 mL formaldehyde and 40 mL distilled water join in there-necked flask, after ultrasonic mix homogeneously, with 250
R/min is stirred, and is warming up to 60oC, adds 2 mg FITC, is incubated 30 min.
(2) in the pre-reaction solution that step (1) obtains, add 4 mL ammonia, after reacting 24 h, add 1 mol/L hydrochloric acid
Solution, regulation pH is to neutral, and reaction system is cooled to room temperature.
(3) it is centrifuged separating by 5000 r/min by the product of step (2), the most respectively with distilled water, ethanol, steaming
Distilled water is cleaned three times, is finally dried 4 h in vacuum drying oven.
The foregoing is only presently preferred embodiments of the present invention, all impartial changes done according to scope of the present invention patent with
Modify, all should belong to the covering scope of the present invention.
Claims (5)
1. the preparation method of a self-luminous fluorescent microsphere, it is characterised in that: this fluorescent microsphere is with phenol, formaldehyde or glutaraldehyde
For raw material, use the self-luminous fluorescent microsphere that modified St ber method prepares.
The preparation method of self-luminous fluorescent microsphere the most according to claim 1, it is characterised in that: by phenol, formaldehyde or penta
Dialdehyde is uniform by ultrasonic disperse, and with ammonia as catalyst, at relatively low temperature, (reaction temperature is not higher than 95oC) sol is passed through under
The course of reaction of gel, the self-luminous fluorescent microsphere described in preparation.
The preparation method of self-luminous fluorescent microsphere the most according to claim 1 or claim 2, it is characterised in that: specifically comprise the following steps that
(1) by 1.0 g phenol, 1.5 mL-6 mL formaldehyde or glutaraldehyde and 40 mL distilled water join in there-necked flask ultrasonic mixed
Close uniformly, be stirred with 250 r/min, be warming up to 50-95oC, is incubated 30 min；
(2) in the pre-reaction solution that step (1) obtains, add 10 L-10 mL ammonia, after reaction 2-24 h, add 1
Mol/L hydrochloric acid solution, regulation pH is to neutral, and reaction system is cooled to room temperature；
(3) product of step (2) is separated by centrifugal method, clean three with distilled water, ethanol, distilled water the most respectively
Secondary, in vacuum drying oven, finally it is dried 4 h.
4. according to the preparation method of the arbitrary described self-luminous fluorescent microsphere of claim 1-3, it is characterised in that: described preparation
Method is modified St ber method；Ammonia is catalyst；Preparation process need not add emulsifying agent or other auxiliary agent.
5. the fluorescent microsphere that the self-luminous fluorescent microsphere preparation method as described in claim 1-4 is arbitrary prepares, its feature
It is: described fluorescent microsphere is self luminous, is expanded the luminescent properties of microsphere by additional fluorescent dye.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113248674A (en) * | 2021-04-12 | 2021-08-13 | 深圳大学 | Polymer particle, preparation method and carbon-based material |
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| CN104907019A (en) * | 2015-04-29 | 2015-09-16 | 复旦大学 | Magnetic fluorescent Raman double-encoding composite microspheres and preparation method and application thereof |
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2016
- 2016-06-12 CN CN201610403025.5A patent/CN106084160B/en active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101333273A (en) * | 2008-07-29 | 2008-12-31 | 华中科技大学 | Method for preparing high molecular fluorescent microballoons |
| CN104907019A (en) * | 2015-04-29 | 2015-09-16 | 复旦大学 | Magnetic fluorescent Raman double-encoding composite microspheres and preparation method and application thereof |
Non-Patent Citations (2)
| Title |
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| JIAN LIU ET AL: "Extension of The Stöber Method to the Preparation of Monodisperse Resorcinol–Formaldehyde Resin Polymer and Carbon Spheres", 《ANGEW.CHEM.INT.ED.》 * |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113248674A (en) * | 2021-04-12 | 2021-08-13 | 深圳大学 | Polymer particle, preparation method and carbon-based material |
| CN113248674B (en) * | 2021-04-12 | 2023-11-14 | 深圳大学 | Polymer particles, preparation method and carbon-based material |
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