CN114015389A - Composite optical membrane and preparation method thereof - Google Patents
Composite optical membrane and preparation method thereof Download PDFInfo
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- CN114015389A CN114015389A CN202111331601.7A CN202111331601A CN114015389A CN 114015389 A CN114015389 A CN 114015389A CN 202111331601 A CN202111331601 A CN 202111331601A CN 114015389 A CN114015389 A CN 114015389A
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/02—Diffusing elements; Afocal elements
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/22—Esters containing halogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C09J133/16—Homopolymers or copolymers of esters containing halogen atoms
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/003—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/11—Anti-reflection coatings
- G02B1/118—Anti-reflection coatings having sub-optical wavelength surface structures designed to provide an enhanced transmittance, e.g. moth-eye structures
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- Optics & Photonics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention provides a composite optical membrane and a preparation method thereof, belonging to the technical field of optical membrane preparation, wherein the composite optical membrane comprises at least one layer of diffusion film and at least one layer of brightness enhancement film, the diffusion film and the brightness enhancement film are compounded together through an adhesive, the adhesive is a modified acrylate adhesive, and the modified acrylate adhesive comprises the following components in parts by weight: 40-70 parts of modified monomer, 30-60 parts of reactive diluent monomer and 3-6 parts of photoinitiator; according to the invention, the modified monomer is prepared by modifying and grafting polyfluoroalkyl on the acryloyl monomer, and based on the strong polarity of polyfluoro groups, the monomer and the polymerized and cured product are endowed with good antistatic performance on the basis of keeping good light transmittance of the acrylate adhesive.
Description
Technical Field
The invention relates to the technical field of optical diaphragm preparation, in particular to a composite optical diaphragm and a preparation method thereof.
Background
The composite optical membrane is obtained by gluing an optical substrate and an optical functional membrane through an optical adhesive, wherein the polymer adhesive is a core component of the composite optical membrane, and the properties of the adhesive directly influence various physical and chemical properties of the optical membrane. With the diversification of the functional requirements of the optical film, higher requirements are provided for a coating material, namely a high-molecular adhesive, and how to synthesize the high-molecular adhesive with excellent comprehensive performances such as optical performance, mechanical property, yellowing resistance, low temperature resistance, hydrolysis resistance and the like so as to meet the requirement of the optical film on application in different fields draws wide attention.
Adhesives currently used to prepare optical films can be broadly classified into three types: acrylates, polyurethanes, silicones, the most common of which are acrylates and polyurethanes; the acrylate adhesive is generally formed into a film by adopting a thermosetting mode and a UV curing mode, compared with the thermosetting mode, the UV curing mode has the advantages of low energy consumption, no volatile organic gas, fast curing, wide application range and the like, and is gradually marketed.
Disclosure of Invention
In order to solve the problems, the invention provides a composite optical film and a preparation method thereof.
The purpose of the invention is realized by adopting the following technical scheme:
the composite optical membrane comprises at least one diffusion film layer and at least one brightness enhancement film layer, wherein the diffusion film layer and the brightness enhancement film layer are compounded together through a transparent adhesive, and the transparent adhesive is a modified acrylate adhesive.
Preferably, the modified acrylate adhesive comprises the following components in parts by weight: 40-70 parts of modified monomer, 30-60 parts of reactive diluent monomer and 3-6 parts of photoinitiator, wherein the modified monomer comprises a first modified monomer;
the preparation method of the first modified monomer comprises the following steps:
(1) weighing acryloyl chloride monomers and dissolving the acryloyl chloride monomers in tetrahydrofuran under the condition of ice-water bath to prepare a solution with the concentration of 0.3-0.4mol/L, sequentially adding polyfluoroalkyl alcohol and triethylamine solution, fully stirring and mixing, stirring and reacting for 4-6h at room temperature to obtain a first mixed solution, decompressing and concentrating the first mixed solution, adding dichloromethane extraction products, adding 1-4mol/L hydrochloric acid solution for washing, separating an organic phase, adding anhydrous sulfate of sodium and/or magnesium, drying overnight, and filtering to obtain a second mixed solution;
wherein the mole ratio of the acryloyl chloride monomer to the polyfluoroalkyl alcohol to the triethylamine is (1-3): 1: (3.8-4.2);
(2) purifying and separating the second mixed solution by a silica gel chromatographic column, removing unreacted monomers to obtain eluent, concentrating under reduced pressure to obtain concentrated solution, adding a mixed solvent of n-hexane and ethanol until no precipitate is formed, separating out the precipitate, and washing with the mixed solvent to obtain the first modified monomer;
wherein the particle size of the silica gel is 300-500 meshes, and the volume ratio of the mobile phase is 1: (1-2) a mixed solvent of n-hexane and dichloromethane.
Preferably, the modifying monomer comprises a second modifying monomer, and the preparation method of the second modifying monomer comprises the following steps:
s1, under the protective atmosphere, taking toluene as a reaction solvent, sequentially adding tetralin, methyl methacrylate and tributylamine, fully stirring and mixing, adding a bis (triphenylphosphine) indenyl ruthenium chloride compound as a polymerization catalyst, and continuously stirring and reacting for 1-2h at 80-90 ℃ to obtain a third mixed solution; preparing a 2-chloro-2-phenylacetic acid ethyl ester solution with the concentration of 0.2-0.3mol/L by taking methylbenzene as a solvent, adding the 2-chloro-2-phenylacetic acid ethyl ester solution into the third mixed solution, continuously preserving heat, stirring and reacting for 4-5 hours, quickly cooling a reaction system after the reaction is finished, filtering and removing the solvent to prepare a fifth mixed solution;
wherein the molar ratio of tetralin, methyl methacrylate, tributylamine and bis (triphenylphosphine) indenyl ruthenium chloride compound is (0.5-0.6): 10: (0.1-0.2): (0.01-0.02); the molar ratio of the methyl methacrylate to the ethyl 2-chloro-2-phenylacetate is 100: 1;
s2, under a protective atmosphere, taking toluene as a reaction solvent, and sequentially adding titanium tetraisopropoxide and allyl alcohol, wherein the molar ratio of the titanium tetraisopropoxide to the allyl alcohol is 8: (5-6); stirring and reacting continuously for 0.5-1h at 80-90 ℃ after fully stirring and mixing, cooling the reaction system quickly after the reaction is finished, adding a toluene solvent after the catalytic product isopropanol is removed by evaporation, sequentially adding the fifth mixed solution and allyl alcohol, stirring and mixing fully, reacting continuously for 20-24h at 80-90 ℃, cooling the reaction system quickly after the reaction is finished, and removing the solvent by evaporation to obtain the second modified monomer.
Preferably, the reactive diluent monomer comprises one or more of methyl methacrylate, butyl methacrylate, isobornyl methacrylate and ethylene glycol dimethacrylate.
Preferably, the toluene is treated with CaH2Drying and pressurizing to dry, and removing the polymerization inhibitor from the reactive diluent monomer through reduced pressure distillation treatment.
Preferably, the diffusion film comprises a substrate layer and a light diffusion layer, wherein the substrate layer is a transparent substrate and has a thickness of 150-; the light diffusion layer is arranged on the upper surface and/or the lower surface of the base material layer.
Preferably, the brightness enhancement film is selected from one or two of a prism film and a micro-lens film; the prism film comprises a substrate layer and a microprism brightening structural layer, and the microprism brightening structural layer is arranged on the upper surface of the substrate layer; the prism film comprises a substrate layer and a microprism brightening structural layer, and the microprism brightening structural layer is arranged on the upper surface of the substrate layer.
Preferably, the base material of the prism film and the microlens film is selected from one of Polycarbonate (PC), polyethylene terephthalate (PET), polyamide resin (PA), Polystyrene (PS), Polyethylene (PE), and polymethyl methacrylate (PMMA).
On the other hand, the invention also provides a preparation method of the composite optical film, which comprises the following steps:
(1) respectively preparing a diffusion film and a brightness enhancement film;
(2) sequentially adding the modified monomer and the reactive diluent monomer according to the weight ratio, uniformly mixing, then adding the photoinitiator according to the weight part, stirring and reacting for 2 hours at 45 ℃, pouring the mixture into a brown bottle after vacuum defoaming, and preserving at low temperature to obtain the modified acrylate adhesive;
(3) and compounding at least one diffusion film and at least one brightness enhancement film together through the modified acrylate adhesive.
On the other hand, the invention also provides a display screen, which consists of the composite optical film, a backlight source and a panel.
The invention has the beneficial effects that:
aiming at the defects of high curing hardness and poor antistatic performance of an acrylate adhesive in the prior art, the invention provides a modified acrylate adhesive and a composite optical membrane prepared from the modified acrylate adhesive, and further, the modified acrylate adhesive improves the antistatic performance of the adhesive by adding a first modified monomer; furthermore, the invention also carries out ester exchange on allyl alcohol, a terminal group chlorine atom and ethyl phenylacetate substituted polymethacrylate to prepare a long-chain telechelic prepolymer with terminal polymerization activity, and copolymerizes the long-chain telechelic prepolymer with a modified monomer to further improve the flexibility of the adhesive product, and has excellent optical and mechanical properties.
Detailed Description
The invention is further described with reference to the following examples.
Example 1
The present embodiments relate to a composite optical film comprising at least one layer of diffuser film and at least one layer of brightness enhancement film;
the diffusion film comprises a substrate layer and a light diffusion layer, wherein the substrate layer is a transparent substrate and has the thickness of 150-400 mu m; the light diffusion layer is arranged on the upper surface and/or the lower surface of the base material layer;
the brightness enhancement film is selected from one or two of a prism film and a micro-lens film; the prism film comprises a substrate layer and a microprism brightening structural layer, and the microprism brightening structural layer is arranged on the upper surface of the substrate layer; the prism film comprises a substrate layer and a microprism brightening structural layer, and the microprism brightening structural layer is arranged on the upper surface of the substrate layer;
the base material of the prism film and the microlens film is selected from one of Polycarbonate (PC), polyethylene terephthalate (PET), polyamide resin (PA), Polystyrene (PS), Polyethylene (PE) and polymethyl methacrylate (PMMA);
the diffusion film and the brightness enhancement film are compounded together through a transparent adhesive, the transparent adhesive is a modified acrylate adhesive, and the modified acrylate adhesive comprises the following components in parts by weight: 40 parts of modified monomer, 50 parts of reactive diluent monomer and 11734 parts of photoinitiator, wherein the modified monomer comprises a first modified monomer;
the preparation method of the first modified monomer comprises the following steps:
(1) weighing 8g of acryloyl chloride monomer under the ice-water bath condition, dissolving the acryloyl chloride monomer in 250mL of anhydrous tetrahydrofuran, adding 5g of perfluoroalkyl alcohol and 17g of triethylamine solution after full dissolution, stirring and mixing the mixture fully, reacting the mixture for 4 hours at room temperature to obtain a first mixed solution, concentrating the first mixed solution under reduced pressure, adding dichloromethane extraction product, adding 2mol/L hydrochloric acid solution for washing, separating an organic phase, adding anhydrous magnesium sulfate, drying overnight, and filtering to obtain a second mixed solution;
(2) purifying and separating the second mixed solution by a silica gel chromatographic column, removing unreacted monomers to obtain eluent, concentrating under reduced pressure to obtain concentrated solution, adding a mixed solvent of n-hexane and ethanol until no precipitate is formed, separating out the precipitate, and washing with the mixed solvent to obtain the first modified monomer;
wherein the particle size of the silica gel is 300-500 meshes, and the volume ratio of the mobile phase is 1: (1-2) a mixed solvent of n-hexane and dichloromethane;
the reactive diluent monomer comprises methyl methacrylate, isobornyl methacrylate, butyl methacrylate and ethylene glycol dimethacrylate, and the mass ratio of the reactive diluent monomer is 1: 1: 2: and 1, removing the polymerization inhibitor from the reactive diluent monomer through reduced pressure distillation treatment.
Example 2
The difference from example 1 is that: the modifying monomer comprises 20wt.% of a second modifying monomer, and the preparation method of the second modifying monomer comprises the following steps:
s1, under the protection of argon, taking toluene as a reaction solvent, sequentially adding 2g of tetralin, 30g of methyl methacrylate and 0.056g of tributylamine into 150mL of toluene solution, fully stirring and mixing, adding 0.05g of bis (triphenylphosphine) indenyl ruthenium chloride compound as a polymerization catalyst, and continuously stirring and reacting at 80-90 ℃ for 1-2h to obtain a third mixed solution; weighing 0.82g of 2-chloro-2-phenylacetic acid ethyl ester, preparing a 2-chloro-2-phenylacetic acid ethyl ester solution with the concentration of 0.2-0.3mol/L by taking toluene as a solvent, adding the 2-chloro-2-phenylacetic acid ethyl ester solution into the third mixed solution, continuing to perform heat preservation and stirring reaction for 4-5 hours, quickly cooling a reaction system after the reaction is finished, filtering and removing the solvent to prepare a fifth mixed solution;
s2, under the protection of argon, taking toluene as a reaction solvent, and sequentially adding 2.27g of titanium tetraisopropoxide and 0.36g of allyl alcohol into 25mL of toluene solution; stirring continuously at 80-90 ℃ for 0.5-1h after fully stirring and mixing, cooling the reaction system quickly after the reaction is finished, adding a toluene solvent to the initial amount after the catalytic product isopropanol is removed by evaporation, sequentially adding the fifth mixed solution and 0.36g of allyl alcohol, stirring and mixing fully, continuing to stir at 80-90 ℃ for 20-24h, cooling the reaction system quickly after the reaction is finished, and removing the solvent by evaporation to obtain the second modified monomer;
the toluene is treated with CaH2Drying and drying under pressure.
Example 3
The difference from example 2 is that: the modifying monomer comprises 50wt.% of a second modifying monomer.
Comparative example
The difference from example 1 is that: the adhesive does not contain a modifying monomer.
The composite optical films prepared in examples 1 to 3 and comparative example were tested for their indices including light transmittance, flexibility, peeling force, and antistatic property, and the test results were as follows:
finally, it should be noted that the above embodiments are only used for illustrating the technical solutions of the present invention, and not for limiting the protection scope of the present invention, although the present invention is described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions can be made on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention.
Claims (10)
1. The composite optical membrane is characterized by comprising at least one diffusion film layer and at least one brightness enhancement film layer, wherein the diffusion film layer and the brightness enhancement film layer are compounded together through a transparent adhesive, and the transparent adhesive is a modified acrylate adhesive.
2. The composite optical film according to claim 1, wherein the modified acrylate adhesive comprises the following components in parts by weight: 40-70 parts of modified monomer, 30-60 parts of reactive diluent monomer and 3-6 parts of photoinitiator, wherein the modified monomer comprises a first modified monomer;
the preparation method of the first modified monomer comprises the following steps:
(1) weighing acryloyl chloride monomers and dissolving the acryloyl chloride monomers in tetrahydrofuran under the condition of ice-water bath to prepare a solution with the concentration of 0.3-0.4mol/L, sequentially adding polyfluoroalkyl alcohol and triethylamine solution, fully stirring and mixing, stirring and reacting for 4-6h at room temperature to obtain a first mixed solution, decompressing and concentrating the first mixed solution, adding dichloromethane extraction products, adding 1-4mol/L hydrochloric acid solution for washing, separating an organic phase, adding anhydrous sulfate of sodium and/or magnesium, drying overnight, and filtering to obtain a second mixed solution;
wherein the mole ratio of the acryloyl chloride monomer to the polyfluoroalkyl alcohol to the triethylamine is (1-3): 1: (3.8-4.2);
(2) purifying and separating the second mixed solution by a silica gel chromatographic column, removing unreacted monomers to obtain eluent, concentrating under reduced pressure to obtain concentrated solution, adding a mixed solvent of n-hexane and ethanol until no precipitate is formed, separating out the precipitate, and washing with the mixed solvent to obtain the first modified monomer;
wherein the particle size of the silica gel is 300-500 meshes, and the volume ratio of the mobile phase is 1: (1-2) a mixed solvent of n-hexane and dichloromethane.
3. The composite optical film according to claim 1, wherein the modifying monomer comprises a second modifying monomer, and the preparation method of the second modifying monomer comprises the following steps:
s1, under the protective atmosphere, taking toluene as a reaction solvent, sequentially adding tetralin, methyl methacrylate and tributylamine, fully stirring and mixing, adding a bis (triphenylphosphine) indenyl ruthenium chloride compound as a polymerization catalyst, and continuously stirring and reacting for 1-2h at 80-90 ℃ to obtain a third mixed solution; preparing a 2-chloro-2-phenylacetic acid ethyl ester solution with the concentration of 0.2-0.3mol/L by taking methylbenzene as a solvent, adding the 2-chloro-2-phenylacetic acid ethyl ester solution into the third mixed solution, continuously preserving heat, stirring and reacting for 4-5 hours, quickly cooling a reaction system after the reaction is finished, filtering and removing the solvent to prepare a fifth mixed solution;
wherein the molar ratio of tetralin, methyl methacrylate, tributylamine and bis (triphenylphosphine) indenyl ruthenium chloride compound is (0.5-0.6): 10: (0.1-0.2): (0.01-0.02); the molar ratio of the methyl methacrylate to the ethyl 2-chloro-2-phenylacetate is 100: 1;
s2, under a protective atmosphere, taking toluene as a reaction solvent, and sequentially adding titanium tetraisopropoxide and allyl alcohol, wherein the molar ratio of the titanium tetraisopropoxide to the allyl alcohol is 8: (5-6); stirring and reacting continuously for 0.5-1h at 80-90 ℃ after fully stirring and mixing, cooling the reaction system quickly after the reaction is finished, adding a toluene solvent after the catalytic product isopropanol is removed by evaporation, sequentially adding the fifth mixed solution and allyl alcohol, stirring and mixing fully, reacting continuously for 20-24h at 80-90 ℃, cooling the reaction system quickly after the reaction is finished, and removing the solvent by evaporation to obtain the second modified monomer.
4. The composite optical film as claimed in claim 1, wherein the reactive diluent monomer comprises one or more of methyl methacrylate, butyl methacrylate, isobornyl methacrylate, and ethylene glycol dimethacrylate.
5. The composite optical film of claim 3 wherein said toluene is CaH2Drying and drying under pressure, and distilling the reactive diluent monomer under reduced pressureAnd removing the polymerization inhibitor.
6. The composite optical film as claimed in claim 1, wherein the diffusion film comprises a substrate layer and a light diffusion layer, the substrate layer is a transparent substrate and has a thickness of 150-400 μm; the light diffusion layer is arranged on the upper surface and/or the lower surface of the base material layer.
7. The composite optical film as claimed in claim 1, wherein the brightness enhancement film is selected from one or two of a prism film and a microlens film; the prism film comprises a substrate layer and a microprism brightening structural layer, and the microprism brightening structural layer is arranged on the upper surface of the substrate layer; the prism film comprises a substrate layer and a microprism brightening structural layer, and the microprism brightening structural layer is arranged on the upper surface of the substrate layer.
8. The composite optical film as claimed in claim 6 or 7, wherein the base material of the prism film and the microlens film is selected from one of polycarbonate, polyethylene terephthalate, polyamide resin, polystyrene, polyethylene, and polymethyl methacrylate.
9. A method of making a composite optical film according to any one of claims 1 to 8, comprising the steps of:
(1) respectively preparing a diffusion film and a brightness enhancement film;
(2) sequentially adding the modified monomer and the reactive diluent monomer according to the weight ratio, uniformly mixing, then adding the photoinitiator according to the weight part, stirring and reacting for 2 hours at 45 ℃, pouring the mixture into a brown bottle after vacuum defoaming, and preserving at low temperature to obtain the modified acrylate adhesive;
(3) and compounding at least one diffusion film and at least one brightness enhancement film together through the modified acrylate adhesive.
10. A display screen comprising the composite optical film of any one of claims 1-8, a backlight, and a panel.
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CN115958841A (en) * | 2022-12-28 | 2023-04-14 | 宜兴威尼特集装袋有限公司 | Preparation process of laminating valve port bag |
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