CN115404020A - Acrylic optical adhesive film with three-layer structure for fully-laminated and flexible folding screen and preparation method thereof - Google Patents
Acrylic optical adhesive film with three-layer structure for fully-laminated and flexible folding screen and preparation method thereof Download PDFInfo
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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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
- C08G18/6415—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63 having nitrogen
- C08G18/6438—Polyimides or polyesterimides
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
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- 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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
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- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/10—Adhesives in the form of films or foils without carriers
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- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/20—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive itself
- C09J2301/208—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive itself the adhesive layer being constituted by at least two or more adjacent or superposed adhesive layers, e.g. multilayer adhesive
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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Abstract
The invention discloses an acrylic optical adhesive film with a three-layer structure for a fully-laminated and flexible folding screen and a preparation method thereof. The invention does not use solvent for auxiliary polymerization, has the characteristics of high reaction conversion rate, low environmental pollution, high curing speed and simple process, overcomes the adverse effects caused by residual solvent and unreacted monomers, and is beneficial to maintaining high light transmittance and recoverability of the product.
Description
Technical Field
The invention relates to the technical field of application of adhesive materials, in particular to an acrylic optical adhesive film with a three-layer structure for a full-lamination and flexible folding screen and a preparation method thereof.
Background
With the large-scale application of flexible displays, optically Clear Adhesives (OCAs) made of acrylic resins have been widely used in the production of foldable display panels. The optical cement of the type needs to be resistant to high loop measurement, resistant to bending while having high transmittance, and free of crease and chromatic aberration after being bent for a long time. The existing OCA optical cement generally has the problem of low elasticity, and various defects are easily generated under the action of external stress. The OCA optical cement needs to have high restorability so as to be able to recover to an original state when stress is removed. Conventional optical glues have difficulty in adequately relieving applied stresses that can lead to defects in the assembled display, such as stress corrosion, delamination, cracking, and fatigue, resulting in reduced lifetime.
It is a feasible solution to improve the performance of acrylic optical glues by modifying them. Chinese patent CN107236496A discloses a polyurethane acrylic acid low shrinkage liquid optical cement based on rosin modification and a preparation method thereof, and the preparation method specifically comprises the following steps: extracting rosin resin from Pinaceae plants, uniformly mixing the rosin resin with acrylic acid, alkyl acrylate and acrylamide, adding water, acetone, an emulsifier and an initiator into a reaction kettle, heating and uniformly stirring, cooling to room temperature, and adjusting the pH value to be alkalescent to obtain a rosin-modified acrylic prepolymer; uniformly stirring and mixing the rosin-modified acrylic prepolymer, polyurethane acrylic resin, isobornyl methacrylate and a spiro-orthomonoacid ester expansion monomer, adding a photoinitiator, a coupling agent and a plasticizer, stirring, and removing bubbles to obtain the rosin-modified polyurethane acrylic low-shrinkage liquid optical adhesive. The liquid optical adhesive prepared by the invention utilizes rosin to modify an acrylic prepolymer and combines a spiro orthomonoacid ester expansion monomer to improve the problem of curing shrinkage of the liquid optical adhesive. However, the invention adopts a solvent polymerization mode, the reaction conversion rate is lower, and residual monomers may exist in a finished product; in addition, in the process of curing to form a film, water and acetone are difficult to ensure to be effectively removed, solvent molecules remained in or on the adhesive film are not beneficial to ensuring the full-lamination property of the optical adhesive, and the structural defects caused by the solvent molecules are also likely to reduce the light transmittance of the optical adhesive, so that the large-scale application in the field is not beneficial.
The photocuring has the characteristics of high reaction conversion rate and no need of solvent in the curing process. Chinese patent CN104004489A provides preparation of an anti-yellowing liquid optical adhesive, and the invention prepares the liquid optical adhesive with high refraction, high light transmittance (> 99%), moisture and heat resistance, no yellowing, ultralow hardness (Shore E2-10) and low volume shrinkage by mutually matching epoxy acrylate resin, aliphatic polyurethane acrylate resin and aromatic polyurethane acrylate resin and adding a monofunctional reactive diluent with low volume shrinkage. The patent uses aromatic urethane acrylate resin, however, in the internal structure of the aromatic polymer material, there may be strong intramolecular or intermolecular charge transfer interaction, and a charge transfer complex is easily formed between the electron donor and the electron acceptor, in the process, due to transition and transfer of charges, the optical cement generates significant absorption to visible light, so that the color and transmittance of the optical cement are deteriorated.
Disclosure of Invention
In view of the above-mentioned drawbacks of the prior art, the present invention provides an acrylic optical adhesive film with full-lamination and excellent flexibility and a method for preparing the same.
The invention prepares and uses an acrylic resin, which takes 2,2' -bis (3,4-dicarboxylic acid) hexafluoropropane dianhydride and 3- (aminomethyl) hexan-1-ol as initial raw materials, and after imidization reaction combination, the acrylic resin further carries out nucleophilic addition reaction with L-lysine diisocyanate, and the obtained product is polymerized with 2-4-hydroxypropyl acrylate to obtain an oligomer. The low polymer is mixed with isobornyl acrylate and ethoxy ethyl acrylate according to a proportion to obtain the acrylic resin. The acrylic OCA optical adhesive prepared from the acrylic resin is crosslinked in the photocuring process, so that the formed optical adhesive film has good adhesive force to OCA layers on two sides, has strong restorability, and meets the use requirement of the flexible folding screen.
According to the invention, the acrylic OCA optical cement prepared from acrylic resin is combined with the existing OCA optical cement to form a three-layer structure, the upper OCA layer and the lower OCA layer are soft in colloid, low in elastic modulus and beneficial to bubble removal, high in segment difference filling rate, and the middle acrylic OCA optical cement layer is hard in colloid, so that the whole elasticity of the glue is increased and the whole glue is beneficial to whole tearing and reworking when the glue is clamped between the two layers of glue and beneficial to die cutting.
A preparation method of an acrylic optical adhesive film with a three-layer structure for a full-lamination and flexible folding screen comprises the following steps:
s1, uniformly mixing acrylic resin, a cross-linking agent and a photoinitiator to obtain an acrylic OCA optical adhesive for later use;
s2, coating OCA optical adhesive on one surface of the release film by using an automatic coating device, and curing by using ultraviolet light to obtain a first OCA adhesive layer; coating the acrylic OCA optical adhesive on the first OCA adhesive layer, and performing ultraviolet curing to obtain a second OCA adhesive layer; coating OCA optical adhesive on the second OCA adhesive layer, attaching a release film, and performing ultraviolet curing to obtain a third OCA adhesive layer; the optical adhesive film with the three-layer OCA adhesive layer structure is the acrylic optical adhesive film with the three-layer structure for the fully-laminated and flexible folding screen.
Preferably, the ratio of the components of the acrylic OCA optical cement in step S1 is: 0.3 to 1.5 weight percent of cross-linking agent, 0.5 to 3.5 weight percent of photoinitiator and the balance of acrylic resin.
The acrylic oligomer prepared by the invention contains a fluorinated aromatic imine structure and a flexible long methylene chain, and has good compatibility with an interface layer and high adhesive force during coating. Since the whole resin shows hydrophobicity, the residual of moisture existing in the environment at the interface is little during curing, so that the defect of the optical adhesive film is reduced, and excellent optical performance is shown.
The aromatic imine structure in the acrylic oligomer molecular chain has certain rigidity, and is helpful for enhancing the mechanical property of the optical adhesive film after curing. The ether oxygen bond structure of the ethoxy ethyl acrylate endows the product with good flexibility and restorability, and the long-chain structure of the ethoxy ethyl acrylate can overcome the steric hindrance of the functional group of the acrylic oligomer and is better combined with the base film during curing. The fluorinated isopropenyl group increases the free volume of the molecule and inhibits the formation of intermolecular or intramolecular charge transfer; the group has strong polarity, so that the charge is difficult to move, and the phenomenon that the color and the light transmittance of the material are deteriorated due to the transition and the transfer of the charge is greatly relieved.
Preferably, the preparation method of the acrylic resin comprises the following steps of:
m1, under the anaerobic condition, uniformly mixing 19.0-25.0 parts of 2,2' -bis (3,4-dicarboxylic acid) hexafluoropropane dianhydride, 13.8-18.0 parts of 3- (aminomethyl) hexan-1-ol and 200-275 parts of N, N-dimethylformamide to obtain a reaction mixed solution; continuously adding 35-45 parts of toluene into the reaction mixed solution, uniformly mixing, heating and carrying out imidization reaction; removing toluene by distillation after the imidization reaction is finished, pouring a reaction product into water with the temperature of 0-4 ℃, filtering and collecting a filter cake, washing the filter cake with water until an eluate is neutral, and then drying to obtain an imidization product for later use;
m2, under the anaerobic condition, dissolving 17.4 to 22.6 parts of the imidization product in 15 to 25 parts of acetone, continuously adding 11.8 to 15.3 parts of L-lysine diisocyanate into the solution, stirring uniformly, continuously adding 0.1 to 0.2 part of dibutyltin dilaurate, and heating under the catalysis of dibutyltin dilaurate to carry out nucleophilic addition reaction; obtaining a polymerization reaction stock solution for later use after the nucleophilic addition reaction is finished;
m3, continuously adding 7.5-10.0 parts of 2-acrylic acid-4-hydroxypropyl into the polymerization reaction stock solution under an anaerobic condition, uniformly mixing and carrying out polymerization reaction; after the polymerization reaction is finished, pouring a reaction product into water at 0-4 ℃, filtering and collecting a filter cake, washing the filter cake with water until the washing liquid is neutral, and then drying to obtain an acrylic oligomer for later use;
and M4, mixing the acrylic oligomer, the ethoxy ethyl acrylate and the isobornyl acrylate according to a ratio until the components are uniform to obtain the acrylic resin.
More preferably, the imidization reaction in the step M1 is carried out at a reaction temperature of 115 to 130 ℃ for 4 to 10 hours.
Further preferably, the reaction temperature of the nucleophilic addition reaction in the step M2 is 30-50 ℃ and the reaction time is 0.5-3 h.
More preferably, the polymerization reaction in the step M3 has a reaction temperature of 25 to 35 ℃ and a reaction time of 1.5 to 4 hours.
More preferably, in the acrylic resin in the step M4, the mass ratio of the acrylic oligomer, the ethoxyethoxyethyl acrylate, and the isobornyl acrylate is 12 to 19:8 to 20:11.
preferably, in step S1, the crosslinking agent is any one of ethylene glycol dimethacrylate, 1,4-butanediol diacrylate, diethylene glycol diacrylate, allyl methacrylate, 1,6-hexanediol diacrylate, and ethylene glycol diacrylate.
Preferably, the ultraviolet irradiation amount of the photo-curing in the step S2 is 2100 to 4000mJ/cm independently of each other 2 The curing time is 5-15 min respectively.
On the basis of the common general knowledge in the field, the above preferred conditions can be combined randomly to obtain the preferred embodiments of the invention.
The introduction and the function of part of raw materials in the formula of the invention are as follows:
isobornyl acrylate: organic matter with molecular formula of C 13 H 20 O 2 . It is used in adhesive and special paint and has high activity, high hardness and low shrinkage. The IBOA is used as the reactive diluent in the radiation curing coating, so that the viscosity of the coating can be effectively reduced, the construction performance is improved, and the leveling property of the coating is improved.
Ethoxyethoxyethyl acrylate: the organic matter is colorless or yellow transparent liquid, is applied to ink, wood, plastics, paper coating and solder resist ink, and has the characteristics of low shrinkage, good flexibility and excellent dilutability.
The invention has the beneficial effects that:
compared with the prior art, the acrylic OCA optical cement prepared from acrylic resin is combined with the existing OCA optical cement to form a three-layer structure, the upper OCA layer and the lower OCA layer are soft in colloid, low in elastic modulus and beneficial to bubble removal, the section difference filling rate is high, the middle acrylic OCA optical cement layer is hard, and the acrylic OCA optical cement layer is clamped between the two layers of cement and beneficial to die cutting, and meanwhile the overall elasticity of the cement is increased, so that the whole piece of cement is beneficial to tearing and reworking.
Compared with the prior art, the low polymer is prepared from 2,2' -bis (3,4-dicarboxylic acid) hexafluoropropane dianhydride, 3- (aminomethyl) hexan-1-ol, L-lysine diisocyanate and 2-acrylic acid-4-hydroxypropyl ester serving as raw materials. The oligomer is mixed with isobornyl acrylate and ethoxy ethyl acrylate in certain proportion to obtain the novel acrylic resin. The optical adhesive film formed by photocuring has good adhesive force and strong restorability, and can not be layered after being folded for many times, so that the use requirement of the flexible folding screen is met.
Compared with the prior art, the acrylic resin has a fluorinated aromatic imine structure and a flexible long methylene chain, and has good compatibility with an interface layer and high adhesive force when being coated. The fluorinated isopropenyl group increases the free volume of the molecule and inhibits the formation of intermolecular or intramolecular charge transfer; the group has strong polarity, so that the charge is difficult to move, and the phenomenon that the color and the light transmittance of the material are deteriorated due to the transition and the transfer of the charge is greatly relieved.
Detailed Description
The invention is further illustrated by the following examples, which are not intended to limit the scope of the invention. The experimental methods without specifying specific conditions in the following examples were selected according to the conventional methods and conditions, or according to the commercial instructions.
Some raw material parameters in the comparative examples and examples of the invention are as follows:
from type membrane, model: r502TE, thickness: 0.05mm, provided by Shenzhen Ruihua coating science and technology Limited;
the OCA optical cement is prepared according to the method described in CN113249038A embodiment 3;
2,2' -bis (3,4-dicarboxylic acid) hexafluoropropane dianhydride, CAS No.: 1107-00-2;
4,4' -oxydiphthalic anhydride, CAS number: 1823-59-2;
3- (aminomethyl) hex-1-ol, CAS No.: 1354953-13-1;
l-lysine diisocyanate, CAS No.: 45172-15-4;
4-hydroxypropyl 2-acrylate, CAS No.: 2478-10-6;
isobornyl acrylate, CAS number: 5888-33-5;
ethoxyethoxyethyl acrylate, CAS No.: 7328-17-8;
ethylene glycol diacrylate, CAS No.: 2274-11-5;
photoinitiator, brand Ai Jianmeng IGM, model number: omnirad 127D, offered by Gvain New materials, inc., guangzhou.
Example 1
An acrylic optical adhesive film with a three-layer structure for a full-lamination and flexible folding screen is prepared by the following method:
s1, uniformly mixing acrylic resin, glycol diacrylate and a photoinitiator to obtain acrylic OCA optical cement for later use;
s2, coating OCA optical adhesive on one surface of the release film by using an automatic coating device, and curing by using ultraviolet light to obtain a first OCA adhesive layer; coating the acrylic OCA optical adhesive on the first OCA adhesive layer, and curing by ultraviolet light to obtain a second OCA adhesive layer; coating OCA optical adhesive on the second OCA adhesive layer, attaching a release film, and carrying out ultraviolet curing to obtain a third OCA adhesive layer; the optical adhesive film with the three-layer OCA adhesive layer structure is the acrylic optical adhesive film with the three-layer structure for the fully-laminated and flexible folding screen.
The acrylic OCA optical cement in the step S1 comprises the following components in proportion: 1.5wt% of ethylene glycol diacrylate, 3.5wt% of photoinitiator and the balance of acrylic resin.
The coating weight of the coating in the step S2 is 0.8g/m 2 (ii) a The ultraviolet irradiation amount of the ultraviolet curing is 3400mJ/cm 2 The curing time was 7min.
The preparation method of the acrylic resin comprises the following steps:
m1, under the protection of nitrogen, uniformly mixing 19.0kg of 2, 2' -bis (3,4-dicarboxylic acid) hexafluoropropane dianhydride, 13.8kg of 3- (aminomethyl) hexan-1-ol and 200kg of N, N-dimethylformamide to obtain a reaction mixed solution; continuously adding 35kg of toluene into the reaction mixed solution, uniformly mixing, heating and carrying out imidization reaction, wherein the reaction temperature is 120 ℃, and the reaction time is 6 hours; after the imidization reaction is finished, removing toluene by distillation, pouring a reaction product into water at 4 ℃, filtering and collecting a filter cake, washing the filter cake with water until an eluate is neutral, and then drying to obtain an imidization product for later use;
m2, under the protection of nitrogen, dissolving 17.4kg of the imidization product in 15kg of acetone, continuously adding 11.8kg of L-lysine diisocyanate into the solution, stirring uniformly, continuously adding 0.1kg of dibutyltin dilaurate, and heating under the catalysis of dibutyltin dilaurate to perform nucleophilic addition reaction, wherein the reaction temperature is 40 ℃ and the reaction time is 1.5h; obtaining a polymerization reaction stock solution for later use after the nucleophilic addition reaction is finished;
m3, under the protection of nitrogen, continuously adding 7.5kg of 2-4-hydroxypropyl acrylate into the polymerization reaction stock solution, uniformly mixing, and carrying out polymerization reaction at the reaction temperature of 30 ℃ for 3h; after the polymerization reaction is finished, pouring the reaction product into water at 4 ℃, filtering and collecting a filter cake, washing the filter cake with water until the washing liquid is neutral, and then drying to obtain the acrylic acid oligomer for later use;
m4, mixing the acrylic oligomer and isobornyl acrylate according to a mass ratio of 19:11 until the components are uniformly mixed to obtain the acrylic resin.
Example 2
An acrylic optical adhesive film with a three-layer structure for a full-lamination and flexible folding screen is prepared by the following method:
s1, uniformly mixing acrylic resin, glycol diacrylate and a photoinitiator to obtain acrylic OCA optical cement for later use;
s2, coating OCA optical adhesive on one surface of the release film by using an automatic coating device, and curing by using ultraviolet light to obtain a first OCA adhesive layer; coating the acrylic OCA optical adhesive on the first OCA adhesive layer, and performing ultraviolet curing to obtain a second OCA adhesive layer; coating OCA optical adhesive on the second OCA adhesive layer, attaching a release film, and carrying out ultraviolet curing to obtain a third OCA adhesive layer; the optical adhesive film with the three-layer OCA adhesive layer structure is the acrylic optical adhesive film with the three-layer structure for the fully-laminated and flexible folding screen.
The acrylic OCA optical cement in the step S1 comprises the following components in proportion: 1.5wt% of ethylene glycol diacrylate, 3.5wt% of photoinitiator and the balance of acrylic resin.
The coating weight of the coating in the step S2 is 0.8g/m 2 (ii) a The ultraviolet irradiation amount of the ultraviolet curing is 3400mJ/cm 2 The curing time was 7min.
The preparation method of the acrylic resin comprises the following steps:
m1, under the protection of nitrogen, mixing 19.0kg of 2, 2' -bis (3,4-dicarboxylic acid) hexafluoropropane dianhydride, 13.8kg of 3- (aminomethyl) hexan-1-ol and 200kg of N, N-dimethylformamide uniformly to obtain a reaction mixed solution; continuously adding 35kg of toluene into the reaction mixed solution, uniformly mixing, heating and carrying out imidization reaction, wherein the reaction temperature is 120 ℃, and the reaction time is 6 hours; after the imidization reaction is finished, removing toluene by distillation, pouring a reaction product into water at 4 ℃, filtering and collecting a filter cake, washing the filter cake with water until an eluate is neutral, and then drying to obtain an imidization product for later use;
m2, under the protection of nitrogen, dissolving 17.4kg of the imidization product in 15kg of acetone, continuously adding 11.8kg of L-lysine diisocyanate into the solution, stirring uniformly, continuously adding 0.1kg of dibutyltin dilaurate, and heating under the catalysis of dibutyltin dilaurate to perform nucleophilic addition reaction, wherein the reaction temperature is 40 ℃ and the reaction time is 1.5h; obtaining a polymerization reaction stock solution for later use after the nucleophilic addition reaction is finished;
m3, under the protection of nitrogen, continuously adding 7.5kg of 2-4-hydroxypropyl acrylate into the polymerization reaction stock solution, uniformly mixing, and carrying out polymerization reaction at the reaction temperature of 30 ℃ for 3h; after the polymerization reaction is finished, pouring the reaction product into water at 4 ℃, filtering and collecting a filter cake, washing the filter cake with water until the washing liquid is neutral, and then drying to obtain the acrylic acid oligomer for later use;
m4, mixing the acrylic oligomer and the ethoxyethoxyethyl acrylate according to a mass ratio of 19:20 until the components are uniformly mixed to obtain the acrylic resin.
Example 3
An acrylic optical adhesive film with a three-layer structure for a full-lamination and flexible folding screen is prepared by the following method:
s1, uniformly mixing acrylic resin, glycol diacrylate and a photoinitiator to obtain acrylic OCA optical cement for later use;
s2, coating OCA optical cement on one surface of the release film by using an automatic coating device, and curing by using ultraviolet light to obtain a first OCA adhesive layer; coating the acrylic OCA optical adhesive on the first OCA adhesive layer, and performing ultraviolet curing to obtain a second OCA adhesive layer; coating OCA optical adhesive on the second OCA adhesive layer, attaching a release film, and carrying out ultraviolet curing to obtain a third OCA adhesive layer; the optical adhesive film with the three-layer OCA adhesive layer structure is the acrylic optical adhesive film with the three-layer structure for the fully-laminated and flexible folding screen.
The acrylic OCA optical cement in the step S1 comprises the following components in proportion: 1.5wt% of ethylene glycol diacrylate, 3.5wt% of photoinitiator and the balance of acrylic resin.
The coating weight of the coating in the step S2 is 0.8g/m 2 (ii) a The ultraviolet irradiation amount of the ultraviolet curing is 3400mJ/cm 2 The curing time was 7min.
The preparation method of the acrylic resin comprises the following steps:
m1, under the protection of nitrogen, mixing 19.0kg of 2, 2' -bis (3,4-dicarboxylic acid) hexafluoropropane dianhydride, 13.8kg of 3- (aminomethyl) hexan-1-ol and 200kg of N, N-dimethylformamide uniformly to obtain a reaction mixed solution; continuously adding 35kg of toluene into the reaction mixed solution, uniformly mixing, heating and carrying out imidization reaction, wherein the reaction temperature is 120 ℃, and the reaction time is 6 hours; after the imidization reaction is finished, removing toluene by distillation, pouring a reaction product into water at 4 ℃, filtering and collecting a filter cake, washing the filter cake with water until an eluate is neutral, and then drying to obtain an imidization product for later use;
m2, under the protection of nitrogen, dissolving 17.4kg of the imidization product in 15kg of acetone, continuously adding 11.8kg of L-lysine diisocyanate into the solution, stirring uniformly, continuously adding 0.1kg of dibutyltin dilaurate, and heating under the catalysis of dibutyltin dilaurate to perform nucleophilic addition reaction, wherein the reaction temperature is 40 ℃ and the reaction time is 1.5h; obtaining a polymerization reaction stock solution for later use after the nucleophilic addition reaction is finished;
m3, under the protection of nitrogen, continuously adding 7.5kg of 2-acrylic acid-4-hydroxypropyl into the polymerization reaction stock solution, uniformly mixing, and carrying out polymerization reaction at the reaction temperature of 30 ℃ for 3 hours; after the polymerization reaction is finished, pouring the reaction product into water at 4 ℃, filtering and collecting a filter cake, washing the filter cake with water until the washing liquid is neutral, and then drying to obtain the acrylic acid oligomer for later use;
m4, mixing the acrylic oligomer, ethoxyethoxyethyl acrylate and isobornyl acrylate according to a mass ratio of 19:20:11 until the components are uniformly mixed to obtain the acrylic resin.
Example 4
An acrylic optical adhesive film with a three-layer structure for a full-lamination and flexible folding screen is prepared by the following method:
s1, uniformly mixing acrylic resin, glycol diacrylate and a photoinitiator to obtain acrylic OCA optical cement for later use;
s2, coating OCA optical adhesive on one surface of the release film by using an automatic coating device, and curing by using ultraviolet light to obtain a first OCA adhesive layer; coating the acrylic OCA optical adhesive on the first OCA adhesive layer, and curing by ultraviolet light to obtain a second OCA adhesive layer; coating OCA optical adhesive on the second OCA adhesive layer, attaching a release film, and performing ultraviolet curing to obtain a third OCA adhesive layer; the optical adhesive film with the three-layer OCA adhesive layer structure is the acrylic optical adhesive film with the three-layer structure for the fully-laminated and flexible folding screen.
The acrylic OCA optical cement in the step S1 comprises the following components in proportion: 1.5wt% of ethylene glycol diacrylate, 3.5wt% of photoinitiator and the balance of acrylic resin.
The coating weight of the coating in the step S2 is 0.8g/m 2 (ii) a The ultraviolet irradiation amount of the ultraviolet curing is 3400mJ/cm 2 The curing time was 7min.
The preparation method of the acrylic resin comprises the following steps:
m1, under the protection of nitrogen, uniformly mixing 13.3kg of 4,4' -oxydiphthalic anhydride, 13.8kg of 3- (aminomethyl) hexan-1-ol and 200kg of N, N-dimethylformamide to obtain a reaction mixed solution; continuously adding 35kg of toluene into the reaction mixed solution, uniformly mixing, heating and carrying out imidization reaction, wherein the reaction temperature is 120 ℃, and the reaction time is 6 hours; after the imidization reaction is finished, removing toluene by distillation, pouring a reaction product into water at 4 ℃, filtering and collecting a filter cake, washing the filter cake with water until an eluate is neutral, and then drying to obtain an imidization product for later use;
m2, under the protection of nitrogen, dissolving 13.9kg of the imidization product in 15kg of acetone, continuously adding 11.8kg of L-lysine diisocyanate into the solution, stirring uniformly, continuously adding 0.1kg of dibutyltin dilaurate, and heating under the catalysis of dibutyltin dilaurate to carry out nucleophilic addition reaction, wherein the reaction temperature is 40 ℃ and the reaction time is 1.5 hours; obtaining a polymerization reaction stock solution for later use after the nucleophilic addition reaction is finished;
m3, under the protection of nitrogen, continuously adding 7.5kg of 2-acrylic acid-4-hydroxypropyl into the polymerization reaction stock solution, uniformly mixing, and carrying out polymerization reaction at the reaction temperature of 30 ℃ for 3 hours; after the polymerization reaction is finished, pouring the reaction product into water at 4 ℃, filtering and collecting a filter cake, washing the filter cake with water until the washing liquid is neutral, and then drying to obtain the acrylic acid oligomer for later use;
m4, mixing the acrylic oligomer, ethoxyethoxyethyl acrylate and isobornyl acrylate according to a mass ratio of 19:20:11 until the components are uniformly mixed to obtain the acrylic resin.
Comparative example 1
An acrylic optical adhesive film with a three-layer structure for a full-lamination and flexible folding screen is prepared by the following method:
s1, uniformly mixing acrylic resin, glycol diacrylate and a photoinitiator to obtain acrylic OCA optical cement for later use;
s2, coating OCA optical adhesive on one surface of the release film by using an automatic coating device, and curing by using ultraviolet light to obtain a first OCA adhesive layer; coating the acrylic OCA optical adhesive on the first OCA adhesive layer, and curing by ultraviolet light to obtain a second OCA adhesive layer; coating OCA optical adhesive on the second OCA adhesive layer, attaching a release film, and performing ultraviolet curing to obtain a third OCA adhesive layer; the optical adhesive film with the three-layer OCA adhesive layer structure is the acrylic optical adhesive film with the three-layer structure for the fully-laminated and flexible folding screen.
In the step S1, the acrylic OCA optical cement comprises the following components in proportion: 1.5wt% of ethylene glycol diacrylate, 3.5wt% of photoinitiator and the balance of acrylic resin.
The coating weight of the coating in the step S2 is 0.8g/m 2 (ii) a The ultraviolet irradiation amount of the ultraviolet curing is 3400mJ/cm 2 The curing time was 7min.
The preparation method of the acrylic resin comprises the following steps:
mixing ethoxy ethyl acrylate and isobornyl acrylate according to a mass ratio of 20:11 until the components are uniformly mixed to obtain the acrylic resin.
Test example 1
The light transmittance and haze test of the acrylic optical adhesive film prepared by the invention is carried out according to the specific method and steps in the national standard GB/T2410-2008 "determination of light transmittance and haze of transparent plastic". The sample is a wafer with the diameter of 50mm, the surfaces of the two sides of the sample are flat and parallel, and the sample is free from dust, oil stains, foreign matters, scratches and the like and free from visible internal defects and particles. Preparing three samples in each group, and adjusting a common test group for 48 hours at the temperature of 23 ℃ and the relative humidity of 50% according to the state of GB/T2918-2018 to perform a test; the folding test group is subjected to 90-degree vertical folding 500 times, and then is subjected to test after being adjusted for 48 hours according to the GB/T2918-2018 state in the environment with the temperature of 23 ℃ and the relative humidity of 50%. And (4) obtaining an arithmetic mean value according to the test result, and observing the surface morphology and the layering state of the folding test group samples. The results of the transmittance and haze measurements on the acrylic optical adhesive films are shown in Table 1, and the conditions of the samples after folding treatment are shown in Table 2.
Table 1:
table 2:
| name (R) | With or without crease lines | With or without delamination | Presence or absence of chromatic aberration |
| Example 1 | Is provided with | Is free of | Is provided with |
| Example 2 | Is free of | Is free of | Is provided with |
| Example 3 | Is composed of | Is composed of | Is free of |
| Example 4 | Is provided with | Is provided with | Is provided with |
| Comparative example 1 | Is provided with | Is provided with | Is provided with |
In the application of the optical adhesive film in the field, the optical adhesive film should meet the technical indexes that the light transmittance is more than 90 percent and the haze is less than 1 percent; when applied to a display with a folding function, the display needs to have the characteristics of bending resistance, no crease after bending, no chromatic aberration and no influence on light transmittance. As can be seen from the test results in tables 1 and 2, example 3 has the best optical properties, and can maintain good light transmittance and low haze even after being folded for many times. The result of this phenomenon may be that the fluorinated isopropenyl group increases the free volume of the molecule, inhibiting the formation of intermolecular or intramolecular charge transfer; the group has strong polarity, so that the charge is difficult to move, and the phenomenon that the color and the light transmittance of the material are deteriorated due to the transition and the transfer of the charge is greatly relieved.
Test example 2
The environmental adaptability test of the acrylic optical adhesive film prepared by the invention is carried out according to the specific method and steps in the national standard GB/T26331-2010 optical thin film element environmental adaptability test method. The test item is an alternating damp-heat test, a sample is placed for 1h under the standard atmospheric condition and then tested, the pretreated sample is placed in a test box under the standard atmospheric condition, the temperature and the humidity in the test box are adjusted to reach a circulation initial state, timing is started after 10min, and then temperature and humidity adjustment is carried out according to the temperature and humidity requirements shown in figure 2 in section 4.5.2 of the standard. The test severity level is 02 grades, and the cycle times are 10 times. After the test is finished, the sample is directly taken out from the test box for recovery treatment, is firstly washed by deionized water or steam room water for 5min, and then is shaken or air flow is used for drying to remove water drops. After the test was completed, the state of the test specimen was evaluated according to the criteria in Table 9 in section 5. The environmental suitability test results of the acrylic optical adhesive film are shown in table 3.
Table 3:
the sample state after the alternating damp-heat test reflects the environmental suitability of the acrylic optical adhesive film, and the test results in table 3 show that the environmental suitability of example 3 is the best. The acrylic oligomer prepared in this example may contain a fluorinated aromatic imine structure and a flexible long methylene chain, and may have good compatibility with the interface layer and high adhesion when coated; because the whole resin shows hydrophobicity, the residue of moisture in the environment at the interface is little during curing, so that the defects of the optical adhesive film are reduced, the three-layer structure is tightly combined, and the adaptability under severe environment is stronger.
Claims (10)
1. The preparation method of the acrylic optical adhesive film with the three-layer structure for the full-lamination and flexible folding screen is characterized by comprising the following steps of:
s1, uniformly mixing acrylic resin, a cross-linking agent and a photoinitiator to obtain an acrylic OCA optical adhesive for later use;
s2, coating OCA optical adhesive on one surface of the release film by using an automatic coating device, and curing by using ultraviolet light to obtain a first OCA adhesive layer; coating the acrylic OCA optical adhesive on the first OCA adhesive layer, and curing by ultraviolet light to obtain a second OCA adhesive layer; coating OCA optical adhesive on the second OCA adhesive layer, attaching a release film, and carrying out ultraviolet curing to obtain a third OCA adhesive layer; the optical adhesive film with the three-layer OCA adhesive layer structure is the acrylic optical adhesive film with the three-layer structure for the fully-laminated and flexible folding screen.
2. The method for preparing the acrylic optical adhesive film with the three-layer structure for the fully-laminated and flexible folding screen according to claim 1, wherein the acrylic OCA optical adhesive in the step S1 comprises the following components in proportion: 0.3 to 1.5 weight percent of cross-linking agent, 0.5 to 3.5 weight percent of photoinitiator and the balance of acrylic resin.
3. The method for preparing the acrylic optical adhesive film with the three-layer structure for the full-lamination and flexible folding screen as claimed in claim 1 or 2, wherein the method for preparing the acrylic resin comprises the following steps in parts by weight:
m1, under the anaerobic condition, uniformly mixing 19.0-25.0 parts of 2,2' -bis (3,4-dicarboxylic acid) hexafluoropropane dianhydride, 13.8-18.0 parts of 3- (aminomethyl) hexan-1-ol and 200-275 parts of N, N-dimethylformamide to obtain a reaction mixed solution; continuously adding 35-45 parts of toluene into the reaction mixed solution, uniformly mixing, heating and carrying out imidization; removing toluene by distillation after the imidization reaction is finished, pouring the reaction product into water at 0-4 ℃, filtering and collecting a filter cake, washing the filter cake with water until the eluate is neutral, and then drying to obtain an imidization product for later use;
m2, under the anaerobic condition, dissolving 17.4 to 22.6 parts of the imidization product in 15 to 25 parts of acetone, continuously adding 11.8 to 15.3 parts of L-lysine diisocyanate into the solution, stirring uniformly, continuously adding 0.1 to 0.2 part of dibutyltin dilaurate, and heating under the catalysis of dibutyltin dilaurate to carry out nucleophilic addition reaction; obtaining a polymerization reaction stock solution for later use after the nucleophilic addition reaction is finished;
m3, continuously adding 7.5-10.0 parts of 2-acrylic acid-4-hydroxypropyl into the polymerization reaction stock solution under an anaerobic condition, uniformly mixing and carrying out polymerization reaction; pouring the reaction product into water at 0-4 ℃ after the polymerization reaction is finished, filtering and collecting a filter cake, washing the filter cake with water until the eluate is neutral, and then drying to obtain the acrylic acid oligomer for later use;
and M4, mixing the acrylic oligomer, the ethoxy ethyl acrylate and the isobornyl acrylate according to a ratio until the components are uniform to obtain the acrylic resin.
4. The method for preparing the acrylic optical adhesive film with the three-layer structure for the full-lamination and flexible folding screen according to claim 3, wherein the method comprises the following steps: the reaction temperature of the imidization reaction in the step M1 is 115-130 ℃, and the reaction time is 4-10 h.
5. The method for preparing the acrylic optical adhesive film with the three-layer structure for the full-lamination and flexible folding screen according to claim 3, wherein the method comprises the following steps: the reaction temperature of the nucleophilic addition reaction in the step M2 is 30-50 ℃, and the reaction time is 0.5-3 h.
6. The method for preparing the acrylic optical adhesive film with the three-layer structure for the fully-laminated and flexible folded screen as claimed in claim 3, wherein the method comprises the following steps: the reaction temperature of the polymerization reaction in the step M3 is 25-35 ℃, and the reaction time is 1.5-4 h.
7. The method for preparing the acrylic optical adhesive film with the three-layer structure for the fully-laminated and flexible folded screen as claimed in claim 3, wherein the method comprises the following steps: in the step M4, the mass ratio of the acrylic oligomer to the ethoxyethoxyethyl acrylate to the isobornyl acrylate in the acrylic resin is 12-19: 8 to 20:11.
8. the method for preparing the acrylic optical adhesive film with the three-layer structure for the full-lamination and flexible folding screen according to claim 1, wherein the method comprises the following steps: in the step S1, the cross-linking agent is any one of ethylene glycol dimethacrylate, 1,4-butanediol diacrylate, diethylene glycol diacrylate, allyl methacrylate, 1,6-hexanediol diacrylate and ethylene glycol diacrylate.
9. The method for preparing the acrylic optical adhesive film with the three-layer structure for the full-lamination and flexible folding screen according to claim 1, wherein the method comprises the following steps: the ultraviolet irradiation amount of the photocuring in the step S2 is 2100 to 4000mJ/cm independently 2 The curing time is 5-15 min respectively.
10. The utility model provides a three layer construction's acrylic acid optical cement membrane for laminating and flexible folding screen entirely which characterized in that: prepared by the method of any one of claims 1 to 9.
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