CN108129595A - A kind of fluorescent copolymer microballoon and preparation method thereof - Google Patents
A kind of fluorescent copolymer microballoon and preparation method thereof Download PDFInfo
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
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Abstract
The present invention relates to a kind of fluorescent copolymer microballoons and preparation method thereof, first by the small molecule fluorescent monomer unsaturation containing amino or hydroxyl, then it is formed using the small molecule unsaturated monomer containing fluorophor with styrene copolymerized, therefore fluorophor is combined closely by chemical bond on polystyrene resin, fluorescent copolymer microballoon and the intermiscibility of aromatic hydrocarbon, chlorohydrocarbon, aliphatic ketone and ester equal solvent are good, fluorescence intensity is high, and fluorophor is not easy to dissociate, and fluorescence timeliness is lasting.Fluorescent copolymer microballoon of the present invention can be widely applied to the fields such as fluorescence probe detection technique, fluorescence chemical sensor, nonlinear optical device, fluorescent ink and fluorescence additive.
Description
Technical field
The present invention relates to a kind of polymer microballoons more particularly to a kind of fluorescent copolymer microballoon and preparation method thereof, belong to
In fluorescent technique field.
Technical background
Fluorescent small molecule tends to come off in the application and, such as traditional dying polymers work bad with base material intermiscibility
Skill tends not to reach requirement.For relative fluorescence small molecule, fluorescent polymer has its feature：Chromophore is existed with chemical bonds
In macromolecule, it is not easy to come off；Chromophore is evenly distributed, stable content, and luminescent properties and light guide are functional, it is therefore necessary to
Study method that fluorescent small molecule is introduced into polymer chain solve fluorescent small molecule is easy to fall off, be unevenly distributed the problems such as.It is glimmering
Photopolymer is the high molecular polymer that fluorescence can be sent out under light radiation.Fluorescence polymer have unique optical physics and
Spectrochemical property has been used as optical resin, fluorescent reagent, scintillator and photon enricher, in fluorescent probe technique, Fluoresceinated
It learns and has wide practical use in the fields such as sensor, nonlinear optical device, microelectronics.
Chinese patent CN1539913A is related to a kind of fluorescent, magnetic, multi-functional nanometer material and preparation method thereof, in water phase or
It is successfully realized in oil phase and coats fluorescent nano material quantum dot and magnetic Nano material in polymer microsphere jointly, obtained
To having the nano material that has fluorescent, magnetic, multi-functional.
Chinese patent CN102516988A discloses a kind of polymerizable fluorescent dye and preparation method thereof, the polymerizable fluorescence
Dyestuff uses the preparation method of emulsion polymerization, can be easily by fluorescent dye using olefinic double bonds Raolical polymerizable
It learns in embedded polymer, does not fall off, while introduce the monomer with benzyl chloride ethylene, form chemical crosslinking site.
Chinese patent CN103571493A discloses a kind of magnetic fluorescent dual-function magnetic microsphere and preparation method thereof, mainly
By superscribing polyaniline macromolecular on magnetic nano-particle surface, it is successfully connected by the function amino of polyaniline molecule end
Fluorescent nano material quantum dot obtains the nanoparticle with magnetic fluorescent dual-function.
The above-mentioned prior art causes fluorescent nano material to be applied widely, but there are still fluorescence intensity, fluorescence timeliness,
Biocompatibility, deficiency and defect with solvent intermiscibility etc., can also continue to be improved in new method.
Invention content
The present invention is intended to provide a kind of fluorescent copolymer microballoon and preparation method thereof.
The present invention is formed using the unsaturated monomer containing fluorophor with styrene copolymerized, and fluorophor passes through chemical bond
It combines closely on polystyrene resin, the phase of fluorescent copolymer microballoon and aromatic hydrocarbon, chlorohydrocarbon, aliphatic ketone and ester equal solvent
Dissolubility is good, and fluorescence intensity is high, and fluorophor is not easy to dissociate, and fluorescence timeliness is lasting.
A kind of fluorescent copolymer microballoon of the present invention, molecular structural formula are as follows：
Wherein, m:1~8, n:1~20.
The shortcomings that overcome the prior art and deficiency, the present invention take following technical scheme, a kind of fluorescence copolymerization
Object microballoon in terms of parts by weight, is prepared by following steps：
(1) synthesis of modified fluorescent monomer：Under nitrogen protection, equipped with blender, condenser pipe, constant pressure addition device and
In the reaction kettle of thermometer, by 10.0~25.0 parts of small molecule fluorescent monomers containing amino or hydroxyl, 0.5~2.0 part of catalysis
Agent, 100.0 parts of organic solvents are added to reactor and are uniformly dissolved, and are slowly dropped into 2.0~10.0 parts of vinyl activated monomers, 1~
2h is dripped off, and 80~120 DEG C are continued 4~6h of reflux, are removed solvent after solution is rotated after filtering insoluble matter, are washed, is so dry that change
Property fluorescent monomer.
(2) dispersin polymerization fluorescent copolymer microballoon dispersion liquid：By the modification fluorescent monomer in 5.0~15.0 parts of steps (1)
It is dissolved in 30.0 parts of styrene, adds in 0.5~1.0 part of stabilizer, 40.0~80.0 parts of water, it is equal by dispersion machine high speed dispersion
It is even to be denoted as a liquid；0.1~0.5 part of initiator is taken to be dissolved completely in 5.0~15.0 parts of alcoholic solvents, initiator solution is obtained and is denoted as b
Liquid；In the reaction kettle equipped with blender, condenser pipe, constant pressure addition device and thermometer, 20.0~30.0 parts of styrene of addition,
30.0~60.0 parts of water, 0.2~1.0 part of stabilizer, 0.1~0.5 part of initiator open stirring and emulsifying it is uniform after be heated to 70~
100 DEG C of 1~2h of reaction, are then added dropwise b liquid, a liquid dropwise respectively, and complete, 70~100 DEG C of the reaction was continued 2~4h are added dropwise in 0.5~1h
Postcooling is to room temperature to get fluorescent copolymer microballoon dispersion liquid.
(3) by the fluorescent copolymer microballoon dispersion liquid centrifugation in step (2), it is heavy that addition alcoholic solvent redisperse centrifuges again
It forms sediment and removes supernatant, vacuum drying is micro- to get a kind of fluorescent copolymer of the present invention that median is 0.1~2 μm for 24 hours
Ball.
The small molecule fluorescent monomer containing amino or hydroxyl preferably comprise amino or the naphthalene replaced containing hydroxyl,
Phenanthrene, anthracene, pyrene at least one, further preferably beta naphthal, 1- naphthols, naphthalidine, 2- naphthylamines, 9- phenanthrol, 9- phenanthrene amine, 1-2-
At least one of (dimethylamino) ethyl -4- methoxyl group -3- phenanthrol, 1- amino pyrenes.
The catalyst is ternary amine, preferably at least one of triethylamine, triethanolamine, picoline.
The organic solvent for benzene,toluene,xylene, ethyl acetate, butyl acetate, acetone, butanone, DMF, DMSO,
At least one of chloroform, pyridine, petroleum ether, n-butyl ether.
The vinyl activated monomer is acryloyl chloride, methacrylic chloride, to vinylbenzoyl chloride, vinyl
At least one of chlorobenzoyl chloride, maleic anhydride, itaconic anhydride, chlorallylene, dichloropropylene.
The stabilizer is at least one of polyvinylpyrrolidone, polyacrylic acid, polyethylene glycol, TX305
The alcoholic solvent is at least one of methanol, ethyl alcohol, normal propyl alcohol, isopropanol.
The initiator is at least one of AIBN, BPO, ammonium persulfate, sodium peroxydisulfate, potassium peroxydisulfate.
It is following (with 9- phenanthrene amine, methacrylic chloride) that a kind of fluorescent copolymer microballoon of the present invention obtains building-up process：
A kind of fluorescent copolymer microballoon of the present invention, can be widely applied to fluorescence probe detection technique, fluorescence chemical
The fields such as sensor, nonlinear optical device, fluorescent ink and fluorescence additive.
Specific embodiment
A kind of fluorescent copolymer microballoon of the present invention and preparation method thereof is further described with reference to embodiment.
It is understood that specific embodiment described herein is used only for explaining related invention rather than the restriction to the invention.
Embodiment 1
A kind of fluorescent copolymer microballoon, in terms of parts by weight, is prepared by following steps：
(1) synthesis of modified fluorescent monomer：Under nitrogen protection, equipped with blender, condenser pipe, constant pressure addition device and
In the reaction kettle of thermometer, 10.0 parts of 2- naphthylamines, 5.0 parts of 9- phenanthrol, 0.5 part of triethanolamine, 100.0 parts of toluene are added to instead
Device is answered to be uniformly dissolved, is slowly dropped into 4.0 parts of acryloyl chlorides, 1h is dripped off, and 80 DEG C are continued the 4h that flows back, and revolve solution after filtering insoluble matter
Solvent is removed after steaming, washs, is so dry that be modified fluorescent monomer.
(2) dispersin polymerization fluorescent copolymer microballoon dispersion liquid：Modification fluorescent monomer in 10.0 parts of steps (1) is dissolved in
In 30.0 parts of styrene, 0.5 part of polyvinyl pyrrole network alkanone, 50.0 parts of water are added in, a is uniformly denoted as by dispersion machine high speed dispersion
Liquid；0.2 part of AIBN is taken to be dissolved completely in 10.0 parts of ethyl alcohol, initiator solution is obtained and is denoted as b liquid；Equipped with blender, condenser pipe,
In the reaction kettle of constant pressure addition device and thermometer, 20.0 parts of styrene, 40.0 parts of water, 0.2 part of polyvinyl pyrrole network alkane are added in
90 DEG C of reaction 2h are heated to after ketone, 0.1 part of AIBN unlatchings stirring and emulsifying are uniform, b liquid, a liquid, 0.5h drops is then added dropwise dropwise respectively
Add complete, 90 DEG C of the reaction was continued 3h postcoolings are to room temperature to get fluorescent copolymer microballoon dispersion liquid.
(3) by the fluorescent copolymer microballoon dispersion liquid centrifugation in step (2), add in after methanol redisperse centrifuge again it is heavy
It forms sediment and removes supernatant, vacuum drying is micro- to get a kind of fluorescent copolymer of the present invention that median is 0.56 μm for 24 hours
Ball.
Embodiment 2
A kind of preparation method of fluorescent copolymer microballoon, in terms of parts by weight, is prepared by following steps：
(1) synthesis of modified fluorescent monomer：Under nitrogen protection, equipped with blender, condenser pipe, constant pressure addition device and
In the reaction kettle of thermometer, by 25.0 parts of 9- phenanthrene amine, 1.0 parts of triethylamines, 100.0 parts of ethyl acetate, it is added to reactor dissolving
Uniformly, 6.0 parts are slowly dropped into styrene formyl chloride, and 1h is dripped off, and 90 DEG C are continued the 5h that flows back, and solution are rotated after filtering insoluble matter
After remove solvent, washing, dry modified fluorescent monomer.
(2) dispersin polymerization fluorescent copolymer microballoon dispersion liquid：Modification fluorescent monomer in 15.0 parts of steps (1) is dissolved in
In 30.0 parts of styrene, 0.6 part of TX305,60.0 parts of water are added in, a liquid is uniformly denoted as by dispersion machine high speed dispersion；Take 0.3 part
Benzoyl peroxide is dissolved completely in 10.0 parts of ethyl alcohol, is obtained initiator solution and is denoted as b liquid；Equipped with blender, condenser pipe, perseverance
In the reaction kettle for pressing feeding device and thermometer, 25.0 parts of styrene, 40.0 parts of water, 0.3 part of TX305,0.4 part of peroxidating are added in
75 DEG C of reaction 1h are heated to after benzoyl unlatching stirring and emulsifying is uniform, b liquid, a liquid is then added dropwise dropwise respectively, 1h is added dropwise completely,
70 DEG C of the reaction was continued 4h postcoolings are to room temperature to get fluorescent copolymer microballoon dispersion liquid.
(3) by the fluorescent copolymer microballoon dispersion liquid centrifugation in step (2), add in after ethyl alcohol redisperse centrifuge again it is heavy
It forms sediment and removes supernatant, vacuum drying is micro- to get a kind of fluorescent copolymer of the present invention that median is 1.23 μm for 24 hours
Ball.
Embodiment 3
A kind of preparation method of fluorescent copolymer microballoon, in terms of parts by weight, is prepared by following steps：
(1) synthesis of modified fluorescent monomer：Under nitrogen protection, equipped with blender, condenser pipe, constant pressure addition device and
In the reaction kettle of thermometer, 15.0 parts of 9- phenanthrol, 10.0 parts of 9- phenanthrene amine, 1.2 parts of picolines, 100.0 parts of dimethylbenzene are added in
It is uniformly dissolved to reactor, is slowly dropped into 10.0 parts of methacrylic chlorides, 1.2h is dripped off, and 100 DEG C are continued the 4h that flows back, and filtering is insoluble
Solvent is removed after solution is rotated after object, washs, is so dry that be modified fluorescent monomer.
(2) dispersin polymerization fluorescent copolymer microballoon dispersion liquid：Modification fluorescent monomer in 15.0 parts of steps (1) is dissolved in
In 30.0 parts of styrene, 1.0 parts of polyvinylpyrrolidone, 80.0 parts of water are added in, a is uniformly denoted as by dispersion machine high speed dispersion
Liquid；0.3 part of ammonium persulfate is taken to be dissolved completely in 10.0 parts of methanol, initiator solution is obtained and is denoted as b liquid；Equipped with blender, cold
In the reaction kettle of solidifying pipe, constant pressure addition device and thermometer, 20.0 parts of styrene, 40.0 parts of water, 0.6 part of polyvinyl pyrrole are added in
80 DEG C of reaction 1h are heated to after pyrrolidone, 0.4 part of ammonium persulfate unlatching stirring and emulsifying are uniform, b liquid, a is then added dropwise dropwise respectively
Liquid, 0.5h are added dropwise complete, and 70~80 DEG C of the reaction was continued 4h postcoolings are to room temperature to get fluorescent copolymer microballoon dispersion liquid.
(3) by the fluorescent copolymer microballoon dispersion liquid centrifugation in step (2), the centrifugation again of ethyl alcohol redisperse is added in
Supernatant is removed, vacuum drying is for 24 hours to get a kind of fluorescent copolymer microballoon of the present invention that median is 1.72 μm.
By the solubility property of a kind of fluorescent copolymer microballoon of the present invention in organic solvent in embodiment 1-3 such as
Following table：
| Solvent | 100g Xylene solubilities | 100g butyl acetate solubility | 100g ethyl acetate solubility |
| Embodiment 1 | 13.26g | 30.96g | 25.02g |
| Embodiment 2 | 14.31g | 33.62g | 26.35g |
| Embodiment 3 | 14.29g | 33.17g | 25.90g |
Although the present invention has been explained in detail and has referred to embodiment, for those of ordinary skill in the art, show
Various schemes, modification and the change that can so make as specified above, should be construed as being included within the scope of the claims.
Claims (10)
1. a kind of fluorescent copolymer microballoon, which is characterized in that using the unsaturated monomer containing fluorophor with it is styrene copolymerized
It forms, fluorophor is combined closely by chemical bond on polystyrene resin, and molecular structural formula is：
Wherein, m:1~8, n:1~20.
2. a kind of preparation method of fluorescent copolymer microballoon as described in claim 1, which is characterized in that in terms of parts by weight,
Include the following steps：
(1) synthesis of modified fluorescent monomer：Under nitrogen protection, equipped with blender, condenser pipe, constant pressure addition device and temperature
In the reaction kettle of meter, by 10.0~25.0 parts of small molecule fluorescent monomers containing amino or hydroxyl, 0.5~2.0 part of catalyst,
100.0 parts of organic solvents are added to reactor and are uniformly dissolved, and are slowly dropped into 2.0~10.0 parts of vinyl activated monomers, 1~2h drops
Complete, 80~120 DEG C are continued 4~6h of reflux, and solvent is removed after solution is rotated after filtering insoluble matter, wash, is dry that modification is glimmering
Light monomer；
(2) dispersin polymerization fluorescent copolymer microballoon dispersion liquid：Modification fluorescent monomer in 5.0~15.0 parts of steps (1) is dissolved
In 30.0 parts of styrene, 0.5~1.0 part of stabilizer, 40.0~80.0 parts of water are added in, are uniformly remembered by dispersion machine high speed dispersion
For a liquid；0.1~0.5 part of initiator is taken to be dissolved completely in 5.0~15.0 parts of alcoholic solvents, initiator solution is obtained and is denoted as b liquid；
In reaction kettle equipped with blender, condenser pipe, constant pressure addition device and thermometer, 20.0~30.0 parts of styrene, 30.0 are added in
70~100 DEG C are heated to after~60.0 parts of water, 0.2~1.0 part of stabilizer, 0.1~0.5 part of initiator unlatching stirring and emulsifying are uniform
React 1~2h, be then added dropwise b liquid, a liquid dropwise respectively, 0.5~1h be added dropwise it is complete, it is cold after 70~100 DEG C of the reaction was continued 2~4h
But to room temperature to get fluorescent copolymer microballoon dispersion liquid；
(3) by the fluorescent copolymer microballoon dispersion liquid centrifugation in step (2), adding in alcoholic solvent redisperse, centrifugation removes again
Supernatant is removed, vacuum drying is for 24 hours to get a kind of fluorescent copolymer microballoon of the present invention that median is 0.1~2 μm.
3. the preparation method of a kind of fluorescent copolymer microballoon according to claim 2, which is characterized in that described contains ammonia
The small molecule fluorescent monomer of base or hydroxyl is the naphthalene containing amino or containing hydroxyl substitution, at least one of phenanthrene, anthracene, pyrene.
4. the preparation method of a kind of fluorescent copolymer microballoon according to claim 3, which is characterized in that described contains ammonia
The small molecule fluorescent monomer of base or hydroxyl is beta naphthal, 1- naphthols, naphthalidine, 2- naphthylamines, 9- phenanthrol, 9- phenanthrene amine, 1-2- (diformazans
Base amino) ethyl -4- methoxyl group -3- phenanthrol, at least one of 1- amino pyrenes.
A kind of 5. preparation method of fluorescent copolymer microballoon according to claim 2, which is characterized in that the catalyst
For at least one of triethylamine, triethanolamine, picoline.
6. the preparation method of a kind of fluorescent copolymer microballoon according to claim 2, which is characterized in that described is organic molten
Agent is benzene,toluene,xylene, ethyl acetate, butyl acetate, acetone, butanone, DMF, DMSO, chloroform, pyridine, petroleum ether, positive fourth
At least one of ether.
A kind of 7. preparation method of fluorescent copolymer microballoon according to claim 2, which is characterized in that the vinyl
Activated monomer is acryloyl chloride, methacrylic chloride, to vinylbenzoyl chloride, vinylbenzoyl chloride, maleic anhydride, clothing
At least one of health acid anhydrides, chlorallylene, dichloropropylene.
A kind of 8. preparation method of fluorescent copolymer microballoon according to claim 2, which is characterized in that the stabilizer
For at least one of polyvinylpyrrolidone, polyacrylic acid, polyethylene glycol, TX305.
A kind of 9. preparation method of fluorescent copolymer microballoon according to claim 2, which is characterized in that the alcoholic solvent
For at least one of methanol, ethyl alcohol, normal propyl alcohol, isopropanol.
A kind of 10. preparation method of fluorescent copolymer microballoon according to claim 2, which is characterized in that the initiation
Agent is at least one of AIBN, BPO, ammonium persulfate, sodium peroxydisulfate, potassium peroxydisulfate.
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| CN111893595A (en) * | 2020-07-09 | 2020-11-06 | 上海慧翌新材料科技有限公司 | Polyester fiber with fluorescent and flame-retardant functions and preparation method thereof |
| CN112295309A (en) * | 2020-10-29 | 2021-02-02 | 杭州原研科技有限公司 | Method for separating fluorescent dye and fluorescent microsphere |
| CN113156782A (en) * | 2021-04-15 | 2021-07-23 | 联想万像(深圳)科技有限公司 | Fluorescent ink powder with uniform charge amount and application thereof |
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| CN113156782A (en) * | 2021-04-15 | 2021-07-23 | 联想万像(深圳)科技有限公司 | Fluorescent ink powder with uniform charge amount and application thereof |
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