CN102911530A - Preparation method capable of realizing chemical blending of modified nano silicon dioxide particles in acrylate monomer - Google Patents
Preparation method capable of realizing chemical blending of modified nano silicon dioxide particles in acrylate monomer Download PDFInfo
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Abstract
改性纳米二氧化硅微粒在丙烯酸酯类单体中化学共混的制备方法涉及用含有丙烯酰氧基的硅烷偶联剂改性纳米二氧化硅微粒在丙烯酸酯类单体中的均匀分散性以及光固化产物在涂料中的应用。改性二氧化硅是通过硅烷偶联剂上的烷氧基和纳米二氧化硅微粒表面的羟基反应，形成牢固的硅氧硅键。含有双键的硅烷偶联剂改性纳米二氧化硅混在单体中。产物光聚合过程中，通过化学键把含有丙烯酰氧基的硅烷偶联剂改性纳米二氧化硅和单体聚合，使得纳米二氧化硅在聚合物中分布的更加均匀。对含有丙烯酰氧基的硅烷偶联剂改性纳米二氧化硅微粒做激光粒径分析和透射电镜分析，对产物做固化分析。目的是提高纳米二氧化硅复合丙烯酸酯类单体在涂料领域的应用。
The preparation method of chemical blending of modified nano-silica particles in acrylate monomers involves modifying the uniform dispersion of nano-silica particles in acrylate monomers with silane coupling agents containing acryloyloxy groups And the application of photocured products in coatings. The modified silica is formed by the reaction of the alkoxy group on the silane coupling agent and the hydroxyl group on the surface of the nano silica particles to form a strong silicon-oxygen-silicon bond. The silane coupling agent modified nano-silica containing double bonds is mixed in the monomer. During the photopolymerization process of the product, the silane coupling agent containing acryloyloxy group is used to modify the nano-silica and the monomer to polymerize through chemical bonds, so that the nano-silica is more uniformly distributed in the polymer. Perform laser particle size analysis and transmission electron microscope analysis on the silane coupling agent-modified nano-silica particles containing acryloyloxy groups, and perform curing analysis on the product. The purpose is to improve the application of nano silicon dioxide composite acrylate monomer in the coating field.
Description
Technical field
The present invention relates to uniformly dispersed and photocuring product the application in coating of silane coupler modified nano silicon dioxide particles in acrylic ester monomer that contains acryloxy.
Background technology
To between the hundreds of nanometer, specific surface area is large, is a kind of white, nontoxic, tasteless, unbodied fine inorganic chemicals product in several nanometers for the atom particle diameter of nano silicon.Have the multiple effects such as good reinforcement, thickening, thixotroping, delustring, uvioresistant and sterilization.The application characteristic of nano silicon in coating: washability, weathering resistance, anti-staining property and self-cleaning property, germ resistance, hydrophobic preservative property, the transparency, raising hardness, thermostability, raising viscosity.Because the good characteristic of nano silicon, nano silicon-organic composite material is used widely in productive life.Inorganic-organic composite material adopts the mode of physical blending usually, namely adopts churned mechanically mode, by Banbury mixer, the standby combination product of extrusion mechanism.The uniformly dispersed very difficult assurance of mineral filler in the product.The present invention is by silane coupler modified nano silicon, and preparation contains the nano silicon of acryloxy, then mixes with monomer, by advanced person's photocuring technology, prepares uniform nano silicon-organic composite material.Photocuring (photopolymerization) refers under UV-light or radiation of visible light, light trigger produces the active specy with initiating activity, these active species energy initiating activity thinner and/or oligopolymer polymerization reaction take places, thus make photocuring system change solid-state process into from liquid state.
Silane coupling agent is in fact the silane that a class has organo-functional group, has simultaneously energy and the chemically combined reactive group of inanimate matter material (such as glass, silica sand, metal etc.) and and the chemically combined reactive group of organic material (synthetic resins etc.) in its molecule.Hydrolysising group---alkoxyl group is such as methoxyl group, oxyethyl group etc.Alkoxyl group can react with the water that adds or inorganic surfaces is residual, and hydrolysis generates silanol, and the then metal hydroxy of these silanols and inorganic surfaces reaction generates the also dehydration of alkoxyl group structure, forms firmly chemical bond.Different organo-functional group comprises amino, methacryloxy, epoxy group(ing), vinyl, sulfydryl etc.Different organo-functional groups is applicable to different organic polymers, and it can carry out chemical reaction (thermoset) with polymkeric substance or form physics twining, passing the network system (thermoplasticity) mutually and form firmly chemical bond.
Nano silicon is used very wide as mineral filler.Wherein, application number 96103689.3 and 00134587.7 Chinese invention patent just carry out physical blending to nano silicon and other polymkeric substance, and nano silicon does not have modification, and the homogeneity that distributes in polymkeric substance and stability can not guarantee.Application number 200610113777.4 Chinese invention patents use silane coupling agent and the polymer blending that contains amino and methyl, and product property is improved, owing to not disperseing when monomer, the homogeneity of silicon-dioxide and stability can not guarantee.Application number 02111816.7 Chinese invention patent uses the silane coupler modified silicon-dioxide of epoxies to be dissolved in monomer, then does thermopolymerization.The dispersion index of thermopolymerization is large.Use contains the silane coupling agent of acryloxy, and by chemical bond linkage nano silicon and monomer, product property is more stable, and nano silicon is evenly distributed.
Summary of the invention
For nano silicon bad dispersibility in acrylic ester monomer of present preparation, storage ability is poor, and the defectives such as industrialization complex steps the object of the invention is to:
(1) provide a kind of modified manometer silicon dioxide particulate can be in acrylic ester monomer Uniform Dispersion and the stable method of depositing.
(2) by chemical bond, inorganic nano silicon-dioxide is connected in the photocuring product, improves wear resistance, weathering resistance and the extinction of product.
The preparation method of a kind of modified manometer silicon dioxide particulate provided by the present invention chemical blend in acrylic ester monomer may further comprise the steps:
(1) preparation of modified manometer silicon dioxide:
Adopt ethanol, methyl alcohol or Virahol to make solvent, add relative solvent quality 0.1%-0.3% hydrochloric acid or relative solvent quality 5%-20% ammoniacal liquor, solvent quality 1%-5% deionized water is made catalyzer relatively, drip and relatively account for solvent quality 10%-25% tetraethoxy, 40-60 ℃ was reacted 5-10 hour, and obtained nano silica microsphere solution;
(2) with the nano silica microsphere solution of preparation in the step (1), logical nitrogen drips silane coupling agent, the mass ratio 1:5-1:20 of silane coupling agent and tetraethoxy; 40-60 ℃ of reaction obtained solution in 12-24 hour;
(3) solution mixes with monomer and purifies: the solution that obtains in the step (2) is mixed with acrylic ester monomer, and the acrylic ester monomer quality is relative solvent quality 3%-7%, carries out purified solution with the method for vacuum rotary steam, after handling, obtains product.In product, the massfraction 30%-50% of modified manometer silicon dioxide.
(4) the laser particle analysis is carried out particle size analysis with the product that obtains in the step (2), analyzes the homogeneity of modified manometer silicon dioxide size distribution.
(5) transmission electron microscope (TEM) carries out TEM (transmission electron microscope) analysis with the product that obtains in the step (2), analyzes size and the pattern of particle.
(6) solidify analysis the product that obtains in the step (3) is added 184/2959/1173/828 light trigger, be coated in uniformly clean slide surface with spreader, in solidifying case, carried out photocuring reaction four minutes, intensity of illumination 40-80mW/cm
-2, observe and the rear sample of test curing.
(7) the product pendulum-rocker hardness after the curing is analyzed the product that obtains in the step (6), solidifies with the monomer that does not add nano silicon to compare.
Described silane coupling agent is: γ-(methacryloxypropyl) propyl trimethoxy silicane, γ-(methacryloxypropyl) propyl group methyl dimethoxysilane, γ-methacryloxypropyl triethoxyl silane, vinyltriethoxysilane, vinyltrimethoxy silane, vinyl three ('beta '-methoxy oxyethyl group) silane, γ-divinyl triammonium propyl group methyl dimethoxysilane or vinyl benzyl amino-ethyl aminopropyl trimethoxysilane.
Described acrylic ester monomer is: 1,6 hexanediol diacrylate HDDA, tri (propylene glycol) diacrylate TPGDA, Viscoat 295 TMPTA, vinylformic acid ten trifluoro monooctyl esters, methacrylic acid ten trifluoro monooctyl esters, Hydroxyethyl acrylate HEA, hydroxyethyl methylacrylate HEMA, polyethylene glycol acrylate, methoxy polyethylene glycol acrylate, polyethyleneglycol diacrylate or polyethylene glycol dimethacrylate.
The present invention relates to form the photo curable acryloyl-oxy group of one deck with containing the silane coupling agent engrafted nanometer silicon dioxide microparticle of acryloxy on the nano silica microsphere surface, increase its uniformly dispersed in acrylic ester monomer.As the additive of photo-cured coating, the present invention can significantly improve wear resistance, weathering resistance and the extinction of coating products.
Use contains the silane coupler modified nano silicon of acryloxy, and the product characteristics in the photopolymerization process, are in the same place silicon-dioxide and monomer polymerization by chemical bond in blend in acrylic ester monomer:
1. improve the stability of nano silicon in polymkeric substance.
2. what nano silicon distributed in polymkeric substance is more even.
3. improve wear resistance and the weathering resistance of polymkeric substance.
4. the characteristics such as photocuring is efficient, energy-conservation have fully been used.
5. improve nano silicon compound acrylic ester class monomer in the application of paint field.
Description of drawings
Fig. 1 embodiment 1 laser particle analysis chart;
Fig. 2 embodiment 1 transmission electron microscope picture.
Embodiment
Embodiment 1:
(1) 2g deionized water, 10ml ammoniacal liquor (analytical pure, massfraction are 25%), 200ml dehydrated alcohol (analytical pure) mixing solutions place 1000ml four-hole boiling flask stirring at normal temperature.Use constant pressure funnel that 20g tetraethoxy (TEOS) is added drop-wise in the flask, 40 ℃ of reaction 5h make nano silicon.Wherein, ammoniacal liquor and deionized water are catalyzer.
(2) nano silicon of preparation in the step (1) is down to room temperature, logical N in solution
2, use constant pressure funnel that 4g γ-methacryloxypropyl base Trimethoxy silane is added drop-wise in the flask after half an hour, dropwise solution and be warming up to 50 ℃, logical N
2Reaction 12h makes modified manometer silicon dioxide.
(3) with the solution and the 14.7g1 that obtain in the step (2), 6-hexanediyl ester monomer mixes, use constant pressure funnel stopper (massfraction 0.5% MEHQ) and 1,6 hexanediol diacrylate monomer dropping in solution, stirring half an hour.Method with vacuum rotary steam is carried out purified solution, and revolving and steaming temperature is 40 ℃, revolves 40 minutes steaming time.After handling, obtain product.Dioxide-containing silica is 30% in the product.
(4) the laser particle analysis is carried out particle size analysis with the product that obtains in the step (2), analyzes the homogeneity of modified manometer silicon dioxide size distribution.Particle is between 80-150nm, and mean diameter is 108.8nm, such as Fig. 1.
(5) transmission electron microscope (TEM) carries out TEM (transmission electron microscope) analysis with the product that obtains in the step (2), analyzes size and the pattern of particle.About white silica dioxide granule 120nm; The size homogeneous evenly distributes, and does not reunite, such as Fig. 2.
(6) solidify 184 light triggers of analyzing the product interpolation massfraction 2% that will obtain in the step (3), be coated in uniformly clean slide surface with spreader, in solidifying case, carried out photocuring reaction 4 minutes, intensity of illumination 40mW/cm
-2, observe and solidify rear sample.Sample surfaces is smooth transparent, completion of cure.
(7) the product pendulum-rocker hardness after the curing is analyzed the product that obtains in the step (6), solidifies with the monomer that does not add nano silicon to compare, and pendulum-rocker hardness is down to 0.54 by 0.76, lower hardness.
Embodiment 2:
(1) 4g deionized water, 20ml ammoniacal liquor (analytical pure, massfraction are 25%), 300ml dehydrated alcohol (analytical pure) mixing solutions place 1000ml four-hole boiling flask stirring at normal temperature.Use constant pressure funnel that 30g tetraethoxy (TEOS) is added drop-wise in the flask, 50 ℃ of reaction 8h make nano silicon.Wherein, ammoniacal liquor and deionized water are catalyzer.
(2) nano silicon of preparation in the step (1) is down to room temperature, logical N in solution
2, use constant pressure funnel that 3g γ-(methacryloxypropyl) propyl group methyl dimethoxysilane is added drop-wise in the flask after half an hour, dropwise solution and be warming up to 50 ℃, logical N
2Reaction 18h makes modified manometer silicon dioxide.
(3) solution that obtains in the step (2) is mixed with 9.45g Viscoat 295 monomer, use constant pressure funnel stopper (massfraction 0.5% MEHQ) and Viscoat 295 monomer dropping in solution, stirring half an hour.Method with vacuum rotary steam is carried out purified solution, and revolving and steaming temperature is 40 ℃, revolves 40 minutes steaming time.After handling, obtain product.Dioxide-containing silica is 40% in the product.
(4) the laser particle analysis is carried out particle size analysis with the product that obtains in the step (2), analyzes the homogeneity of modified manometer silicon dioxide size distribution.Particle is between 80-150nm, and mean diameter is 108.8nm.
(5) transmission electron microscope (TEM) carries out TEM (transmission electron microscope) analysis with the product that obtains in the step (2), analyzes size and the pattern of particle.About white silica dioxide granule 120nm; The size homogeneous evenly distributes, and does not reunite.
(6) solidify 2959 light triggers of analyzing the product interpolation massfraction 2% that will obtain in the step (3), be coated in uniformly clean slide surface with spreader, in solidifying case, carried out photocuring reaction 8 minutes, intensity of illumination 60mW/cm
-2, observe and solidify rear sample.Sample surfaces is smooth transparent, completion of cure.
(7) the product pendulum-rocker hardness after the curing is analyzed the product that obtains in the step (6), solidifies with the monomer that does not add nano silicon to compare, and pendulum-rocker hardness is down to 0.56 by 0.76, lower hardness.
Embodiment 3:
(1) 6g deionized water, 30ml ammoniacal liquor (analytical pure, massfraction are 25%), 400ml dehydrated alcohol (analytical pure) mixing solutions place 1000ml four-hole boiling flask stirring at normal temperature.Use constant pressure funnel that 40g tetraethoxy (TEOS) is added drop-wise in the flask, 60 ℃ of reaction 10h make nano silicon.Wherein, ammoniacal liquor and deionized water are catalyzer.
(2) nano silicon of preparation in the step (1) is down to room temperature, logical N in solution
2, use constant pressure funnel that 2g γ-methacryloxypropyl triethoxyl silane is added drop-wise in the flask after half an hour, dropwise solution and be warming up to 50 ℃, logical N
2Reaction 24h makes modified manometer silicon dioxide.
(3) solution that obtains in the step (2) is mixed with 6.3g methacrylic acid ten trifluoro monooctyl ester monomers, use constant pressure funnel stopper (massfraction 0.5% MEHQ) and methacrylic acid ten trifluoro monooctyl ester monomer droppings in solution, stirring half an hour.Method with vacuum rotary steam is carried out purified solution, and revolving and steaming temperature is 40 ℃, revolves 40 minutes steaming time.After handling, obtain product.Dioxide-containing silica is 50% in the product.
(4) the laser particle analysis is carried out particle size analysis with the product that obtains in the step (2), analyzes the homogeneity of modified manometer silicon dioxide size distribution.Particle is between 80-150nm, and mean diameter is 108.8nm.
(5) transmission electron microscope (TEM) carries out TEM (transmission electron microscope) analysis with the product that obtains in the step (2), analyzes size and the pattern of particle.About white silica dioxide granule 120nm; The size homogeneous evenly distributes, and does not reunite.
(6) solidify 1173 light triggers of analyzing the product interpolation massfraction 2% that will obtain in the step (3), be coated in uniformly clean slide surface with spreader, in solidifying case, carried out photocuring reaction 10 minutes, intensity of illumination 80mW/cm
-2, observe and solidify rear sample.Sample surfaces is smooth transparent, completion of cure.
(7) the product pendulum-rocker hardness after the curing is analyzed the product that obtains in the step (6), solidifies with the monomer that does not add nano silicon to compare, and pendulum-rocker hardness is down to 0.60 by 0.76, lower hardness.
Embodiment 4:
(1) 8g deionized water, 0.2g hydrochloric acid (analytical pure, massfraction are 36%), 200ml dehydrated alcohol (analytical pure) mixing solutions place 1000ml four-hole boiling flask stirring at normal temperature.Use constant pressure funnel that 20g tetraethoxy (TEOS) is added drop-wise in the flask, 40 ℃ of reaction 5h make nano silicon.Wherein, hydrochloric acid and deionized water are catalyzer.
(2) nano silicon of preparation in the step (1) is down to room temperature, logical N in solution
2, use constant pressure funnel that the 4g vinyltriethoxysilane is added drop-wise in the flask after half an hour, dropwise solution and be warming up to 50 ℃, logical N
2Reaction 12h makes modified manometer silicon dioxide.
(3) solution that obtains in the step (2) is mixed with 14.7g Hydroxyethyl acrylate monomer, use constant pressure funnel stopper (massfraction 0.5% MEHQ) and Hydroxyethyl acrylate monomer dropping in solution, stirring half an hour.Method with vacuum rotary steam is carried out purified solution, and revolving and steaming temperature is 40 ℃, revolves 40 minutes steaming time.After handling, obtain product.Dioxide-containing silica is 30% in the product.
(4) the laser particle analysis is carried out particle size analysis with the product that obtains in the step (2), analyzes the homogeneity of modified manometer silicon dioxide size distribution.Particle is between 20-800nm, and mean diameter is 45.2nm.
(5) transmission electron microscope (TEM) carries out TEM (transmission electron microscope) analysis with the product that obtains in the step (2), analyzes size and the pattern of particle.About white silica dioxide granule 50nm; The size homogeneous evenly distributes, and does not reunite.
(6) solidify 184 light triggers of analyzing the product interpolation massfraction 2% that will obtain in the step (3), be coated in uniformly clean slide surface with spreader, in solidifying case, carried out photocuring reaction 4 minutes, intensity of illumination 40mW/cm
-2, observe and solidify rear sample.Sample surfaces is smooth transparent, completion of cure.
(7) the product pendulum-rocker hardness after the curing is analyzed the product that obtains in the step (6), solidifies with the monomer that does not add nano silicon to compare, and pendulum-rocker hardness is down to 0.50 by 0.76, lower hardness.
Embodiment 5:
(1) 10g deionized water, 0.4g hydrochloric acid (analytical pure, massfraction are 36%), 300ml dehydrated alcohol (analytical pure) mixing solutions place 1000ml four-hole boiling flask stirring at normal temperature.Use constant pressure funnel that 40g tetraethoxy (TEOS) is added drop-wise in the flask, 50 ℃ of reaction 8h make nano silicon.Wherein, hydrochloric acid and deionized water are catalyzer.
(2) nano silicon of preparation in the step (1) is down to room temperature, logical N in solution
2, use constant pressure funnel that 2.6g vinyl three ('beta '-methoxy oxyethyl group) silane is added drop-wise in the flask after half an hour, dropwise solution and be warming up to 50 ℃, logical N
2Reaction 18h makes modified manometer silicon dioxide.
(3) solution that obtains in the step (2) is mixed with 9.45g methoxy polyethylene glycol acrylate monomer, use constant pressure funnel stopper (massfraction 0.5% MEHQ) and methoxy polyethylene glycol acrylate monomer dropping in solution, stirring half an hour.Method with vacuum rotary steam is carried out purified solution, and revolving and steaming temperature is 40 ℃, revolves 40 minutes steaming time.After handling, obtain product.Dioxide-containing silica is 40% in the product.
(4) the laser particle analysis is carried out particle size analysis with the product that obtains in the step (2), analyzes the homogeneity of modified manometer silicon dioxide size distribution.Particle is between 20-800nm, and mean diameter is 45.2nm.
(5) transmission electron microscope (TEM) carries out TEM (transmission electron microscope) analysis with the product that obtains in the step (2), analyzes size and the pattern of particle.About white silica dioxide granule 50nm; The size homogeneous evenly distributes, and does not reunite.
(6) solidify 2959 light triggers of analyzing the product interpolation massfraction 2% that will obtain in the step (3), be coated in uniformly clean slide surface with spreader, in solidifying case, carried out photocuring reaction four minutes, intensity of illumination 60mW/cm
-2, observe and solidify rear sample.Sample surfaces is smooth transparent, completion of cure.
(7) the product pendulum-rocker hardness after the curing is analyzed the product that obtains in the step (6), solidifies with the monomer that does not add nano silicon to compare, and pendulum-rocker hardness is down to 0.57 by 0.76, lower hardness.
Embodiment 6:
(1) 4g deionized water, 0.6g hydrochloric acid (analytical pure, massfraction are 36%), 400ml dehydrated alcohol (analytical pure) mixing solutions place 1000ml four-hole boiling flask stirring at normal temperature.Use constant pressure funnel that 50g tetraethoxy (TEOS) is added drop-wise in the flask, 60 ℃ of reaction 10h make nano silicon.Wherein, hydrochloric acid and deionized water are catalyzer.
(2) nano silicon of preparation in the step (1) is down to room temperature, logical N in solution
2, use constant pressure funnel that 2.5g vinyl benzyl amino-ethyl aminopropyl trimethoxysilane is added drop-wise in the flask after half an hour, dropwise solution and be warming up to 50 ℃, logical N
2Reaction 24h makes modified manometer silicon dioxide.
(3) solution that obtains in the step (2) is mixed with 6.3g polyethylene glycol dimethacrylate monomer, use constant pressure funnel stopper (massfraction 0.5% MEHQ) and polyethylene glycol dimethacrylate monomer dropping in solution, stirring half an hour.Method with vacuum rotary steam is carried out purified solution, and revolving and steaming temperature is 40 ℃, revolves 40 minutes steaming time.After handling, obtain product.Dioxide-containing silica is 50% in the product.
(4) the laser particle analysis is carried out particle size analysis with the product that obtains in the step (2), analyzes the homogeneity of modified manometer silicon dioxide size distribution.Particle is between 20-800nm, and mean diameter is 45.2nm.
(5) transmission electron microscope (TEM) carries out TEM (transmission electron microscope) analysis with the product that obtains in the step (2), analyzes size and the pattern of particle.About white silica dioxide granule 50nm; The size homogeneous evenly distributes, and does not reunite.
(6) solidify 1173 light triggers of analyzing the product interpolation massfraction 2% that will obtain in the step (3), be coated in uniformly clean slide surface with spreader, in solidifying case, carried out photocuring reaction four minutes, intensity of illumination 80mW/cm
-2, observe and solidify rear sample.Sample surfaces is smooth transparent, completion of cure.
(7) the product pendulum-rocker hardness after the curing is analyzed the product that obtains in the step (6), solidifies with the monomer that does not add nano silicon to compare, and pendulum-rocker hardness is down to 0.55 by 0.76, lower hardness.
Claims (3)
1. the preparation method of modified manometer silicon dioxide particulate chemical blend in acrylic ester monomer may further comprise the steps:
(1) preparation of modified manometer silicon dioxide:
Adopt ethanol, methyl alcohol or Virahol to make solvent, add relative solvent quality 0.1%-0.3% hydrochloric acid or relative solvent quality 5%-20% ammoniacal liquor, solvent quality 1%-5% deionized water is made catalyzer relatively, drip and relatively account for solvent quality 10%-25% tetraethoxy, 40-60 ℃ was reacted 5-10 hour, and obtained nano silica microsphere solution;
(2) with the nano silica microsphere solution of preparation in the step (1), logical nitrogen drips silane coupling agent, the mass ratio 1:5-1:20 of silane coupling agent and tetraethoxy; 40-60 ℃ of reaction obtained solution in 12-24 hour;
(3) solution mixes with monomer and purifies: the solution that obtains in the step (2) is mixed with acrylic ester monomer, and the acrylic ester monomer quality is relative solvent quality 3%-7%, carries out purified solution with the method for vacuum rotary steam, after handling, obtains product.
2. according to claim 1 preparation method is characterized in that the silane coupling agent described in the step (1) is: γ-(methacryloxypropyl) propyl trimethoxy silicane, γ-(methacryloxypropyl) propyl group methyl dimethoxysilane, γ-methacryloxypropyl triethoxyl silane, vinyltriethoxysilane, vinyltrimethoxy silane, vinyl three ('beta '-methoxy oxyethyl group) silane, γ-divinyl triammonium propyl group methyl dimethoxysilane or vinyl benzyl amino-ethyl aminopropyl trimethoxysilane.
3. according to claim 1 preparation method, it is characterized in that the acrylic ester monomer described in the step (2) is: 1,6 hexanediol diacrylate, tri (propylene glycol) diacrylate, Viscoat 295, vinylformic acid ten trifluoro monooctyl esters, methacrylic acid ten trifluoro monooctyl esters, Hydroxyethyl acrylate, hydroxyethyl methylacrylate, polyethylene glycol acrylate, methoxy polyethylene glycol acrylate, polyethyleneglycol diacrylate or polyethylene glycol dimethacrylate.
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