CN105732883B - A kind of preparation method for the water polyacrylic acid for emitting room temperature phosphorimetry - Google Patents
A kind of preparation method for the water polyacrylic acid for emitting room temperature phosphorimetry Download PDFInfo
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Abstract
The invention discloses a kind of preparation methods for the water polyacrylic acid for emitting room temperature phosphorimetry, it is characterized in first preparing the acrylate monomer that can emit room temperature phosphorimetry, itself and one or more common acrylate monomers are subjected to emulsion copolymerization again, phosphorescent chromophores chemistry is made to be typed into the strand of water polyacrylic acid, makes the water polyacrylic acid prepared that there is Emission at Room Temperature phosphorescence.The water polyacrylic acid for emitting room temperature phosphorimetry prepared using the method for the present invention, it is free from the pure organic electroluminescent light polymer phosphor material of organometallic complex, its building-up process is simple, at low cost, nontoxic, pollution-free, it is applied widely, for phosphorescent chromophores content controllably in 1 10wt%, and chromophore is embedded into the form of chemical bond in polyacrylate molecular, mobility is low, it is lasting to shine, and photoluminescence quantum yield is up to 70%.
Description
Technical field
The invention belongs to function acrylate technical fields, and in particular to can emit the acrylate monomer of room temperature phosphorimetry
The poly- of room temperature phosphorimetry can be emitted by synthesizing and carrying out emulsion copolymerizations formation with other common acrylic ester monomers using the monomer
The preparation method of acrylate.
Background technology
Polymer phosphor material can be divided into two class of electroluminescent and luminescence generated by light, they are in organic electroluminescence device, change
The application value in the fields such as color coating, bio-imaging is increasingly valued by people.It can electroluminescent polymer phosphorescence material
Material is at present mostly by being blended into polymer matrix by organotransition metal complex or organometallic complex being passed through chemistry
Key is directly connected on the main chain or side chain of polymer and is made.Such phosphor material is mainly the organometallic ligand of heavy metal coordination
Close object or polycarbazole, polyfluorene equiconjugate system.Chinese patent CN101663339A discloses a kind of polycarbazole base (methyl) propylene
Acid esters light emitting composition, but since it contains the heavy metal elements such as heavy metal element iridium, platinum, gold, lead, tin, there are toxicity it is big,
Expensive, the defects of synthesis is complicated.Can luminescence generated by light pure organic polymer phosphor material have bio-toxicity it is low, synthesis and
The advantages that preparation process is simple, easy processing and cost are relatively low.Chinese patent 201510311812.2 and the U.S.《ACS application materials
With interface》(ACS Applied Materials＆Interfaces, 17209-17216 pages of 31 phases of volume 7 in 2015) describe
Synthesize that can be prepared by the common small molecule glycol chain extender of replacement on the basis of fluorescence, the double transmitting dihydric alcohols of phosphorescence can be same
When the dual emission type aqueous polyurethane that fluoresces with phosphorescence, synthesis to photoluminescence polymer phosphor material prepares and adds
A kind of new method.But current aqueous polyurethane constrains it and pushes away on a large scale there are the deficiencies of expensive, resistance to acid and alkali is slightly worse
Wide application.
Invention content
Room temperature phosphorimetry is emitted based on room temperature phosphorimetry group in acrylate monomer the purpose of the present invention is to propose to a kind of
Water polyacrylic acid preparation method, with the prepared acrylate monomer that can emit room temperature phosphorimetry and other monomers into
Row binary or multi-component copolymer make obtained water polyacrylic acid have the function of Emission at Room Temperature phosphorescence.
The present invention can emit the preparation method of the water polyacrylic acid of room temperature phosphorimetry, it is characterised in that：First preparing can send out
The acrylate monomer of room temperature phosphorimetry is penetrated, then it is subjected to lotion with other one or more common acrylic ester monomers and is total to
It is poly-, phosphorescent chromophores chemistry is made to be typed into the strand of water polyacrylic acid, is synthesizing water polyacrylic acid lotion
On the basis of, obtained acrylic acid ester emulsion is placed in polytetrafluoroethylene (PTFE) template, controls the steaming of moisture at ambient temperature
Speed is sent out, makes evaporation process control at 5-7 days, the thickness of control water polyacrylic acid film is at 10-200 μm to get to can send out
The water polyacrylic acid film of room temperature phosphorimetry is penetrated, wherein the acrylate monomer that can emit room temperature phosphorimetry accounts for entire strand
Content by adjusting phosphorescence acrylate monomer and the mass ratio of comonomer, is adjusted in the range of 1-10wt% according to actual needs
It is whole；
The preparation of the acrylate monomer that room temperature phosphorimetry can be emitted is in molar ratio by 1:3-8:The halogenated anthracene of 1-2
Quinones organic molecule, methylaminoethanol and potassium hydroxide or potassium carbonate stir and are warming up to 120-140 DEG C, and reaction 10-15 is small
Shi Hou is cooled to room temperature, the water by 15-30 times of volume of methylaminoethanol is added in, after being stirred at room temperature 1-2 hours, through filtering, collecting
Solid sediment with acetone recrystallization, obtains the anthraquinone derivative containing hydroxyl；Then in molar ratio 1:2-4:1-2:20-40
Reaction 12-24 hours is stirred at room temperature in anthraquinone derivative containing hydroxyl, acryloyl chloride, triethylamine and dichloromethane；Reaction solution
Organic phase is collected after being washed with distilled water repeatedly；With volume ratio 1:Tetrahydrofuran/petroleum ether of 4-8 is eluant, eluent, using column layer
Chromatography separating-purifying is analysed, obtains to emit the acrylate monomer of room temperature phosphorimetry, reaction equation is：
R in above-mentioned reaction equation1Group is selected from：
R2Group is selected from：
- CH=CH2Or-C (CH3)=CH2；
The acrylate monomer that room temperature phosphorimetry can be emitted account for entire strand content be 1-10wt% can launch room
Water polyacrylic acid film quality part experimental formula of warm phosphorescence is as follows：
The acrylate monomer that room temperature phosphorimetry can be emitted account for entire strand content be 1-10wt% can launch room
The water polyacrylic acid film of warm phosphorescence is made by following steps：
Be firstly added the emulsifier and water of all-mass, emulsify 15 minutes, add whole phosphorescence acrylate monomers and
The 1/5 of one or more comonomer gross masses emulsifies 30 minutes；60-90 DEG C is warming up to, initiator solution and residue is added dropwise
4/5 mass comonomer, after being added dropwise to complete in 1-3 hours, insulation reaction 2-6 hours, room temperature phosphorimetry can be emitted by synthesizing
Acrylate monomer mass fraction is the water polyacrylic acid lotion for emitting room temperature phosphorimetry of 1-10wt%；
Then obtained acrylic acid ester emulsion is placed in polytetrafluoroethylene (PTFE) template, controls moisture at ambient temperature
Evaporation rate makes evaporation process control at 5-7 days, and the thickness of control water polyacrylic acid film is at 10-200 μm to get to can
The acrylate monomer mass fraction for emitting room temperature phosphorimetry is the water polyacrylic acid for emitting room temperature phosphorimetry of 1-10wt%
Film.
The common acrylic ester monomer be selected from acrylic acid (AA), methyl acrylate (MA), ethyl acrylate (EA),
Hydroxy-ethyl acrylate (HEA), butyl acrylate (BA), methacrylic acid (MAA), methyl methacrylate (MMA), metering system
Acetoacetic ester (MEA), butyl methacrylate (BMA) or hydroxyethyl methacrylate (HEMA).
The emulsifier is selected from lauryl sodium sulfate (SDS), dodecyl sodium sulfate (SDS), dodecyl benzene sulfonic acid
Sodium (SDBS), dodecyl benzene sulfonic acid (DSB) or nekal (SDNS).
The initiator is selected from bis- (2- imidazolines) dihydrochlorides (AIBI) of 2,2 '-azepine, ammonium persulfate (APS), over cure
Sour potassium (KPS) or sodium peroxydisulfate (SPS).
The acrylate monomer of the present invention for emitting room temperature phosphorimetry includes：Acrylic acid 2- [(9,10- dihydros -9,10-
Dioxo -2- anthryls)-Methyl-amino]-ethyl ester, acrylic acid 2- [(the bromo- 9,10- dihydros -9,10- dioxos -2- anthracenes of 6-
Base)-Methyl-amino]-ethyl ester, acrylic acid 2- [(the chloro- 9,10- dihydros -9,10- dioxos -2- anthryls of 5-)-methyl-ammonia
Base]-ethyl ester, 2- methacrylic acids 2- [(9,10- dihydro -9,10- dioxo -2- anthryls)-Methyl-amino]-ethyl ester, 2-
Methacrylic acid 2- [(the bromo- 9,10- dihydros -9,10- dioxos -2- anthryls of 6-)-Methyl-amino]-ethyl ester, 2- metering systems
Sour 2- [(the chloro- 9,10- dihydros -9,10- dioxos -2- anthryls of 5-)-Methyl-amino]-ethyl ester；
Its structural formula is respectively：
The inventive point that the present invention can emit the preparation method of the water polyacrylic acid of room temperature phosphorimetry is to propose one kind
The synthetic method of new pure organic photic phosphorescent polyacrylate, so as to reality there are currently no heavy metal complex under the conditions of
Phosphorescent polyacrylate material is obtained by the way of emulsion polymerization, solve heavy metal complex phosphor material it is toxic,
It is of high cost, the blending defects such as the resistance to mobility of phosphor material is low.Compared with the prior art, the present invention has the following advantages：
1st, the polyacrylate for emitting room temperature phosphorimetry prepared using the method for the present invention, is pure organic electroluminescent light phosphorescence
Phosphorescent chromophores without heavy metal element, and by the way of emulsion copolymerization, are embedded into poly- by polymer material with chemical bond
In acrylate molecule chain, have in the polyacrylate that reaction condition is mild, is formed that chromophore mobility is low, luminescent properties are held
Long stabilization, the advantages that polymerization process is solvent-free, environmental-friendly, nontoxic to organism.
2nd, the polyacrylate for emitting room temperature phosphorimetry prepared using the method for the present invention, due to using binary or polynary common
Poly- method, therefore be easy to control content (1- of the phosphorescent chromophores in polyacrylate molecular as needed
10wt%).
3rd, the polyacrylate for emitting room temperature phosphorimetry prepared using the method for the present invention, maximum absorption band are located at ultra-violet (UV) band
Domain, the yellow phosphorescence that absorbable ultraviolet light emission becomes clear, quantum yield is up to 70%, in Organic Light Emitting Devices, light-induced variable
The fields such as color coating have potential application value.
4th, the polyacrylate for emitting room temperature phosphorimetry prepared using the method for the present invention, because of the ripe letter of emulsion polymerization technique
Many excellent properties single, at low cost and that polyacrylate can be retained, it is applied widely, be conducive to mass produce.
Description of the drawings
Fig. 1 is that the nuclear-magnetism of acrylate monomer (ANAQ) for emitting room temperature phosphorimetry prepared in the embodiment of the present invention 1 is total to
Shake hydrogen spectrogram.
Fig. 2 is the acetate-copolymerized water polyacrylate i.e. butyl methacrylate-propylene prepared in the embodiment of the present invention 2
Fourier (Fourier) transform infrared spectroscopy figure of sour hydroxyl ethyl ester-phosphorescence acrylate terpolymer (ANAQ-WPA).
Fig. 3 is the acetate-copolymerized water polyacrylate solid film of different ANAQ contents prepared in the embodiment of the present invention 3
The photoluminescence emission spectrogram of (ANAQ-WPA-1, ANAQ-WPA-5, ANAQ-WPA-10).
Specific embodiment
Embodiment 1：
1st, 2.1g 2- chloroanthraquinones, 2.0g N methyldiethanol amines and 0.72g potassium hydroxide are added to 50mL single port bottles
In, it stirs and is warming up to 130 DEG C and react 10 hours；It treats that reaction system is cooled to room temperature, reactant is poured into and is distilled equipped with 100mL
Water and with magnetic stir bar 250mL beakers in, quickly stir 1h；It filters and collects red brown solid sediment, use ethyl alcohol
Or up to red brown solid intermediate product 2- [(2- hydroxyethyls)-methylamino]-anthraquinone pure 2.11g after re crystallization from toluene,
Yield is 89%.
2nd, 1.69g 2- [(2- hydroxyethyls)-methylamino]-anthraquinone, 0.91g triethylamines and 15g dichloromethane is added to
In 50mL single port bottles, it is stirred at room temperature until solid is completely dissolved；1.25g2- methacrylic chlorides are dissolved in 5mL dichloromethane
In, it is added drop-wise in single port bottle under the conditions of being stirred at room temperature, and keep dripping off for 30 minutes, reaction 15h is then stirred at room temperature；Reaction knot
Shu Hou, reaction solution distill water washing three times with 50mL in the separatory funnel of 250mL, collect and concentrate organic phase；Use column chromatography
(solvent is tetrahydrofuran and petroleum ether to chromatography separating-purifying, and the two volume ratio is 1:8) 1.91g reddish yellow, is obtained containing phosphorescence
The acrylate monomer 2- methacrylic acids 2- [(9,10- dihydro -9,10- dioxo -2- anthryls)-Methyl-amino] of chromophore -
Ethyl ester (ANAQ), yield 91%.
3rd, 0.67g lauryl sodium sulfate, 15g distilled water are added in 50mL there-necked flasks, stirring and emulsifying 15 minutes；It will
0.101g acrylate and 2g BMA obtained above containing phosphorescent chromophores, which are added in there-necked flask, to be emulsified 30 minutes；Heating is anti-
System is answered to 60 DEG C, by 0.202g 2, bis- (2- imidazolines) dihydrochlorides (AIBI) of 2 '-azepine are dissolved in 5g distilled water, will
AIBI aqueous solutions and 8g butylmethacrylate monomers are added drop-wise in there-necked flask to be dripped off in 2 hours；After insulated and stirred 6h to obtain the final product
To butyl methacrylate-phosphorescence acrylate bipolymer that ANAQ contents are 1wt%.
Fig. 1 is the hydrogen nuclear magnetic resonance spectrogram of the acrylate monomer containing phosphorescent chromophores made from the present embodiment.Respectively
Kind hydrogen chemical shifts δ H (300MHz, CDCl3) ownership be expressed as follows：A (8.28ppm, td, J=7.7,1.9Hz, 2H), b
(8.18ppm, d, J=8.9Hz, 1H), c (7.75ppm, m, 2H), d (7.53ppm, d, J=2.8Hz, 1H), e (7.04ppm,
Dd, J=8.9,2.8Hz, 1H), f (4.41ppm, t, J=5.6Hz, 2H), g (3.86ppm, t, J=5.7Hz, 2H)), h
(3.20ppm, s, 3H), i (1.89ppm, t, J=1.3Hz, 3H), j (6.06ppm, m, 1H), k (5.55ppm, p, J=1.6Hz,
1H)；In addition, the integrated value at all nuclear-magnetism peaks is consistent with theoretical value.It is possible thereby to prove the structure of ANAQ.
It such as keeps other conditions constant, and butyl methacrylate therein (BMA) is substituted for acrylic acid (AA), propylene
Sour methyl esters (MA), ethyl acrylate (EA), hydroxy-ethyl acrylate (HEA), butyl acrylate (BA), methacrylic acid (MAA), first
One or more of groups of base methyl acrylate (MMA), ethyl methacrylate (MEA) or hydroxyethyl methacrylate (HEMA)
Object is closed, can obtain emitting the water polyacrylic acid of room temperature phosphorimetry.
If keeping other conditions constant, and emulsifier is substituted for dodecyl sodium sulfate (SDS), detergent alkylate sulphur
Sour sodium (SDBS), dodecyl benzene sulfonic acid (DSB) or nekal (SDNS) can obtain that room temperature phosphorimetry can be emitted
Water polyacrylic acid.
If keeping other conditions constant, and initiator is substituted for ammonium persulfate (APS), potassium peroxydisulfate (KPS) or mistake
Sodium sulphate (SPS) can obtain emitting the water polyacrylic acid of room temperature phosphorimetry.
Embodiment 2：
1.21g lauryl sodium sulfate and 30g distilled water are added in 150mL there-necked flasks, stirring and emulsifying 15 minutes；It will
0.202g acrylate ANAQ, 2g BMA and 2g HEA obtained above containing phosphorescent chromophores are added in there-necked flask and emulsify 30
Minute；0.4g AIBI are dissolved in 10g distilled water by temperature reaction system to 60 DEG C；By AIBI aqueous solutions, 8g metering systems
Acid butyl ester and 8g hydroxy-ethyl acrylate mix monomers are added drop-wise in there-necked flask and were dripped off in 2 hours；It can be obtained after insulated and stirred 6h
ANAQ contents are butyl methacrylate-hydroxy-ethyl acrylate-phosphorescence acrylate terpolymer (ANAQ-WPA- of 1wt%
1)。
Fig. 2 is the acetate-copolymerized water polyacrylate i.e. methyl-prop for emitting room temperature phosphorimetry prepared in the present embodiment
Fourier (Fourier) transformation of olefin(e) acid butyl ester-hydroxy-ethyl acrylate-phosphorescence acrylate terpolymer (ANAQ-WPA-1)
Infrared spectrogram.3050cm in figure-1, 1635cm-1、1602cm-1、1463cm-1C-H, C=C on anthraquinone radicals phenyl ring are corresponded to respectively
The stretching vibration of skeleton, and 1680cm-1The C=C double bonds characteristic peak of left and right disappears, it was demonstrated that ANAQ has access to polymer molecular chain
In；2924cm-1、2852cm-1Methyl, the stretching vibration peak of methylene, 1728cm respectively in HEA, BMA structural unit-1For C
Stretching vibration peak, the 1156cm of=O-1And 1077cm-1Be respectively C-O-C asymmetric and symmetrics stretching vibration peak in ester group,
1385cm-1It is methyl symmetrical deformation vibration peak, 3360cm-1The peak at place then corresponds to the stretching vibration of O-H in HEA units.Fig. 2 is demonstrate,proved
Understand the structure of obtained ANAQ-WPA-1 in the present embodiment.
Embodiment 3：
2g lauryl sodium sulfate and 30g distilled water are added in 150mL there-necked flasks, stirring and emulsifying 15 minutes；By 2g
ANAQ obtained above, 2g BMA and 2g HEA are added in there-necked flask and emulsify 30 minutes；Temperature reaction system, will to 60 DEG C
0.4g AIBI are dissolved in 10g distilled water；AIBI aqueous solutions, 7g butyl methacrylates and 7g hydroxy-ethyl acrylates are mixed
It was dripped off in 2 hours in monomer dropping to there-necked flask；The methacrylic acid fourth that ANAQ contents are 10% is made after insulated and stirred 6h
Ester-hydroxy-ethyl acrylate-phosphorescence acrylate terpolymer (ANAQ-WPA-10)；It is sent out in a vacuum after film forming
Penetrate the copolymerized waterborne polyacrylate film of room temperature phosphorimetry.
If keeping other conditions constant, change the mass ratio of phosphorescence acrylate monomer and comonomer, can prepare
A series of copolymerized waterborne polyacrylate of phosphorescence acrylate monomer (ANAQ) contents different (1-10wt%).
Fig. 3 is respectively 1%, 5% and 10% for ANAQ contents manufactured in the present embodiment (mass fraction for accounting for total monomer)
Acetate-copolymerized water polyacrylate, that is, ANAQ contents are respectively 1%, 5% and 10% butyl methacrylate-acrylic acid hydroxyl
Ethyl ester-phosphorescence acrylate terpolymer (ANAQ-WPA-1, ANAQ-WPA-5, ANAQ-WPA-10) film is in vacuum condition
Under photoluminescence emission spectrogram, excitation wavelength be 365nm ultraviolet lights.As seen from Figure 3, maximum emission peak is shown in 571-595nm
The characteristic of Yellow light-emitting low temperature is shown；And increase with chromophore content, the red shift of 24nm has occurred in maximum emission peak.
The following table 1 is the methacrylic acid fourth that ANAQ contents (mass fraction for accounting for total monomer) are respectively 1%, 5% and 10%
Ester-hydroxy-ethyl acrylate-luminescence generated by light the phosphorescent lifetime of phosphorescence acrylate terpolymer film under room temperature in vacuum conditions
Attenuation data table.
1 butyl methacrylate of table-hydroxy-ethyl acrylate-phosphorescence acrylate terpolymer film is under vacuum
Luminescence generated by light phosphorescent lifetime attenuation data table
Luminescence generated by light phosphorescent lifetime in upper table is the excitation wave strip in 369nm using Spectral LED lasers light source
It is measured under part and obtained using Data-Station v6.6 (Horiba Scientific) professional software analysis mode, this
The luminescent lifetime of three kinds of phosphorescence water polyacrylic acids all in millisecond magnitude, belongs to room temperature phosphorimetry scope.
Claims (5)
1. a kind of preparation method for the water polyacrylic acid for emitting room temperature phosphorimetry, it is characterised in that：First preparing can launch room
The acrylate monomer of warm phosphorescence, then itself and other one or more acrylic ester monomers are subjected to emulsion copolymerization, make phosphorescence
Chromophore chemistry is typed into the strand of water polyacrylic acid, synthesize can emit room temperature phosphorimetry aqueous polyacrylamide acid
On the basis of ester lotion, the obtained water polyacrylic acid lotion for emitting room temperature phosphorimetry is placed in polytetrafluoroethylene (PTFE) template
In, the evaporation rate of moisture is controlled at ambient temperature, and making evaporation process control, control can emit room temperature phosphorimetry at 5-7 days
The thickness of water polyacrylic acid film at 10-200 μm to get to the water polyacrylic acid film that can emit room temperature phosphorimetry,
In can emit the acrylate monomer of room temperature phosphorimetry and account for the content of entire strand according to actual needs by adjusting can launch room
The mass ratio of the acrylate monomer of warm phosphorescence and other one or more acrylic ester monomers, is adjusted in the range of 1-10wt%
It is whole；
The preparation of the acrylate monomer for emitting room temperature phosphorimetry is in molar ratio by 1:3-8:The halogenated Anthraquinones of 1-2
Organic molecule, methylaminoethanol and potassium hydroxide or potassium carbonate stir and are warming up to 120-140 DEG C, after reaction 10-15 hours,
Room temperature is cooled to, the water by 15-30 times of volume of methylaminoethanol is added in, after being stirred at room temperature 1-2 hours, through filtering, collecting solid
Sediment with acetone recrystallization, obtains the anthraquinone derivative containing hydroxyl；Then in molar ratio 1:2-4:1-2:20-40 will contain
Reaction 12-24 hours is stirred at room temperature in anthraquinone derivative, acryloyl chloride, triethylamine and the dichloromethane for having hydroxyl；Reaction solution steams
Organic phase is collected after distilled water washing repeatedly；With volume ratio 1:Tetrahydrofuran/petroleum ether of 4-8 is eluant, eluent, using column chromatography color
Spectrometry separating-purifying, obtains to emit the acrylate monomer of room temperature phosphorimetry, and reaction equation is：
R in above-mentioned reaction equation1Group is selected from：
R2Group is selected from：
- CH=CH2Or-C (CH3)=CH2；
The acrylate monomer for emitting room temperature phosphorimetry accounts for entire strand content and emits room temperature phosphorus for 1-10wt%
Water polyacrylic acid film quality part experimental formula of light is as follows：
The acrylate monomer for emitting room temperature phosphorimetry accounts for entire strand content and emits room temperature phosphorus for 1-10wt%
The water polyacrylic acid film of light is made by following steps：
The emulsifier and water of all-mass are firstly added, emulsifies 15 minutes, adds the acrylic acid that can all emit room temperature phosphorimetry
The 1/5 of ester monomer and other one or more acrylic ester monomer gross masses emulsifies 30 minutes；60-90 DEG C is warming up to, drop
Add initiator solution and other one or more acrylic ester monomers of remaining 4/5 mass, be added dropwise to complete in 1-3 hours
Afterwards, insulation reaction 2-6 hours, synthesize acrylate monomer mass fraction the sending out for 1-10wt% that can emit room temperature phosphorimetry
Penetrate the water polyacrylic acid lotion of room temperature phosphorimetry；
Then the obtained water polyacrylic acid lotion for emitting room temperature phosphorimetry is placed in polytetrafluoroethylene (PTFE) template, in room
The evaporation rate of moisture is controlled under the conditions of temperature, making evaporation process control, control can emit aqueous poly- the third of room temperature phosphorimetry at 5-7 days
The thickness of olefin(e) acid ester film 10-200 μm to get to can emit room temperature phosphorimetry acrylate monomer mass fraction be 1-10wt%
The water polyacrylic acid film for emitting room temperature phosphorimetry.
2. the preparation method of the water polyacrylic acid of room temperature phosphorimetry can be emitted as described in claim 1, be characterized in that it is described its
His one or more acrylic ester monomers be selected from methyl acrylate, ethyl acrylate, hydroxy-ethyl acrylate, butyl acrylate,
Methyl methacrylate, ethyl methacrylate, butyl methacrylate or hydroxyethyl methacrylate.
3. the preparation method of the water polyacrylic acid of room temperature phosphorimetry can be emitted as described in claim 1, it is characterized in that the breast
Agent is selected from lauryl sodium sulfate, dodecyl sodium sulfate, neopelex, dodecyl benzene sulfonic acid or dibutyl
Sodium naphthalene sulfonate.
4. the preparation method of the water polyacrylic acid of room temperature phosphorimetry can be emitted as described in claim 1, it is characterized in that described and draws
It sends out agent and is selected from 2,2 '-azepine bis- (2- imidazolines) dihydrochloride, ammonium persulfate, potassium peroxydisulfate or sodium peroxydisulfates.
5. the preparation method of the water polyacrylic acid of room temperature phosphorimetry can be emitted as described in claim 1, be characterized in that it is described can
The structural formula of acrylate monomer for emitting room temperature phosphorimetry is respectively：
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| CN102702420A (en) * | 2012-06-18 | 2012-10-03 | 江南大学 | Preparation method of color polyacrylate polymer microspheres |
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| CN102702420A (en) * | 2012-06-18 | 2012-10-03 | 江南大学 | Preparation method of color polyacrylate polymer microspheres |
| CN104927017A (en) * | 2015-06-08 | 2015-09-23 | 中国科学技术大学 | Preparation method for double-emission waterborne polyurethane capable of emitting fluorescence and phosphorescence synchronously |
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