CN110358439B - Low-shrinkage high-hardness high-wear-resistance transparent polyimide hardened film - Google Patents
Low-shrinkage high-hardness high-wear-resistance transparent polyimide hardened film Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/0427—Coating with only one layer of a composition containing a polymer binder
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1687—Use of special additives
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2475/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2475/04—Polyurethanes
- C08J2475/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2227—Oxides; Hydroxides of metals of aluminium
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/011—Nanostructured additives
Abstract
The invention belongs to the technical field of transparent polyimide hardened films, and particularly relates to a low-shrinkage high-hardness high-wear-resistance transparent polyimide hardened film, wherein a hardening liquid for preparing the transparent polyimide hardened film comprises the following components in parts by weight: 50-80 parts of high-functionality polyurethane acrylate, 10-20 parts of multifunctional polyether acrylate, 10-20 parts of flexible monomer, 10-20 parts of reactive diluent, 0.5-2 parts of photoinitiator, 0.05-0.2 part of thermal initiator, 80-150 parts of good solvent, 2-20 parts of high-boiling-point poor solvent, 0.05-1 part of anti-fingerprint auxiliary agent and 10-30 parts of inorganic nano particles. According to the invention, the hardness of the hardened film is improved by adopting high-functionality polyurethane acrylate and multifunctional polyether acrylate, the toughness of the hardened film is improved by the flexible monomer, and meanwhile, the thermal initiator and the photoinitiator are added, and through the cooperation between thermal curing and photo-curing, the shrinkage stress generated by polymerization in the curing process is properly released, so that the generation of warping is avoided.
Description
Technical Field
The invention belongs to the technical field of transparent polyimide hardened films, and particularly relates to a low-shrinkage high-hardness high-wear-resistance transparent polyimide hardened film.
Background
The technique of curved screen has been generally regarded and pursued by consumers and the industry in recent years. With the continuous development and improvement of the fixed curvature curved screen technology in the future, the flexible touch screen capable of realizing arbitrary bending is bound to become an important development direction. Although flexible screens can be bent, if they are bent frequently, they suffer from fatigue problems like metal paper. If multiple bending and prolonged use are performed, the flexible screen may suffer from a crease in the middle of the screen after being subjected to multiple compressive and tensile stresses. In addition, circuit boards, components, and the like, when subjected to a large amount of bending and non-bending, may also be damaged or otherwise fail when folded. The existing glass panel can not meet the requirement of high frequency, the transparent polyimide (CPI) film is used for replacing the existing glass cover plate because the transparent Polyimide (PI) film has good foldability, but the Polyimide (PI) material can not meet the requirement of hardness, and a hardening film is required to be added on the surface of the PI film to enhance the hardness.
At present, two main problems exist in the development process of the flexible screen hardening film: firstly, the contradiction between high hardness and low warpage exists, the existing method for improving hardness is to add a large amount of high-functionality monomer into a system to improve the crosslinking degree, while the volume shrinkage can be caused by the conventional vinyl monomer in the UV curing process, and the larger the crosslinking degree is, the more serious the volume shrinkage is; secondly, the contradiction between high hardness and bending is that after the high hardness is obtained by improving the crosslinking density through a large amount of high-functionality monomers, the cured film is generally high in brittleness, the toughness needs to be improved by properly matching flexible monomers, and the structure and the number of the flexible monomers are crucial to whether the cured film can be finally provided with good bending performance.
Disclosure of Invention
In order to solve the contradiction between high hardness, low warpage and bendability, the invention discloses a low-shrinkage high-hardness high-wear-resistance transparent polyimide hardened film, which mainly adopts high-functionality polyurethane acrylate to improve the hardness, is matched with a flexible monomer to improve the toughness, is added with a thermal initiator and a photoinitiator simultaneously, and properly releases the shrinkage stress generated by polymerization in the curing process through the matching between thermal curing and photocuring to obtain the high-hardness low-warpage bendable transparent polyimide hardened film.
In order to achieve the purpose, the invention adopts the following technical scheme:
a hardening liquid for preparing a transparent polyimide hardening film is composed of the following components in parts by weight:
preferably, the high-functionality urethane acrylate is a urethane-modified acrylate oligomer having a functionality of not less than 6, and the multifunctional polyether acrylate is a polyether-modified acrylate oligomer having a functionality of not less than 3.
Preferably, the flexible monomer is monofunctional or difunctional polyether acrylate or polycaprolactone modified acrylate.
Preferably, the polymerization degree of the polyether or polycaprolactone in the polyether-modified acrylate or polycaprolactone-modified acrylate is 2-10.
Preferably, the reactive diluent is one or more of isobornyl methacrylate, tetrahydrofuran methyl acrylate, lauryl acrylate, isodecyl acrylate and polyethoxyethyl acrylate.
Preferably, the photoinitiator is one or more of alpha-hydroxy ketone initiators and acetophenone initiators, the thermal initiator is one or more of peroxy thermal initiators and azo thermal initiators, the half-life period at 70 ℃ of the thermal initiator is not less than 10 hours, and the half-life period at 140 ℃ is not more than 5 minutes.
Preferably, the good solvent is one or more of PGM, IPA, BAC, MEK, and MIBK, and the high-boiling point poor solvent is one or two of ethylene glycol and cyclohexanol.
Preferably, the anti-fingerprint agent is a perfluorovinyl ether reactive surfactant, and the inorganic nanoparticles are nano SiO2Or nano Al2O3。
Preferably, the transparent polyimide hardened film with low shrinkage, high hardness and high wear resistance is prepared by the following method:
(1) uniformly coating the hardening liquid on a transparent polyimide substrate, and then carrying out thermal drying and thermal curing;
(2) and carrying out UV curing, then carrying out annealing treatment, cooling the hardened film, attaching a protective film, and cutting.
Preferably, the thermal drying and thermal curing are carried out at 100-160 ℃ for 2-10 min; the UV curing conditions are as follows: the illumination intensity is 100-500mW/cm2, the light quantity is 300-1000mJ/cm2, and the temperature of the film surface is 40-60 ℃; the annealing treatment is carried out for 2-10min at the temperature of 120-180 ℃.
The invention has the following beneficial effects: (1) according to the invention, the hardness of the hardened film is improved by adopting high-functionality polyurethane acrylate and multifunctional polyether acrylate, the toughness of the hardened film is improved by a flexible monomer, meanwhile, a thermal initiator and a photoinitiator are added, and through the cooperation between thermal curing and photo-curing, the shrinkage stress generated by polymerization in the curing process is properly released, so that the warping is avoided;
(2) the added poor solvents with high boiling points still remain in a system in a trace amount after UV curing is finished, and the poor solvents with high boiling points have low solubility to polymers, are easy to form microphase region aggregation in a coating, and microphase regions are formed among flexible monomers with long branched chains, and finally tend to form a structure with high hardness tending to be separated from a flexible region, so that the good flexibility is realized under the condition of keeping high hardness, and meanwhile, the microphase regions are also beneficial to internal stress generated by curing of a dispersion system, and warping is avoided;
(3) according to the invention, a dual curing mode of thermal curing and photo-curing is adopted, the thermal-initiated free radical prepolymerization is firstly carried out, most shrinkage stress can be generated due to the fact that monomers and oligomers are subjected to prepolymerization in the thermal curing process, and the solvent still exists in the system after the thermal curing process, so that the shrinkage stress generated by polymerization can be effectively eliminated, and therefore, the shrinkage in the thermal curing process can be effectively avoided.
Detailed Description
The present invention will now be described in further detail with reference to examples.
The high functionality urethane acrylates used herein are well-established chemical 6 functionality urethane acrylates (RJ423), 9 functionality urethane acrylates (RJ4217) and 15 functionality urethane acrylates (RJ 4219); the multifunctional polyether acrylates are basf 3.4 functional polyether acrylate (Laromer LR 8997) and 3.5 functional polyether acrylate (Laromer PO 94F), and also tesman 4 functional polyether acrylate (AgiSyn 701) and 4 functional polyether acrylate (AgiSyn 703); the anti-fingerprint additive is Milo AF-JX 82 perfluoropolyether anti-fingerprint oil and a perfluoropolyether anti-fingerprint oil additive HTLC-9633.
The urethane acrylate used in the comparative example was a well-established chemical 2-functional urethane acrylate (RJ 4234); the polyfunctional polyether acrylate used in the comparative example was 2-functional polyether acrylate from Dissmann (AgiSyn 702).
The transparent polyimide (CPI) hardened film with low shrinkage, high hardness and high wear resistance is prepared by the following method:
(1) uniformly coating the hardening liquid on a transparent polyimide substrate, and then carrying out thermal drying and thermal curing;
(2) and carrying out UV curing, then carrying out annealing treatment, cooling the hardened film, attaching a protective film, and cutting.
Wherein, the thermal drying and thermal curing are carried out for 2-10min at the temperature of 100-160 ℃; the UV curing conditions were: the illumination intensity is 100-500mW/cm2, the light quantity is 300-1000mJ/cm2, and the temperature of the film surface is 40-60 ℃; the annealing treatment is carried out for 2-10min under the conditions of 120-180 ℃.
CPI substrates have a thickness of 25-80 μm and a cured film thickness of 3-20 μm, with increased cured film thickness increasing hardness but adversely affecting bending and increasing cost. .
The components and their amounts in parts by weight of examples 1 to 4 and comparative examples 1 to 7 are specified in Table 1.
TABLE 1
The results of the tests on the CPI cured films prepared in examples 1 to 4 and comparative examples 1 to 7 are shown in Table 2.
TABLE 2
The warp data in table 2 refers to the average warp height at the four corners of the a4 sample; the wear resistance test method comprises the following steps: adopting a Minoan eraser, using 1kg of force, measuring the stroke by 40mm at a speed of 40 cycles/min, measuring 3000 circles in a circulating manner, taking 3 points in an area behind the eraser, and measuring the water drop angle; the dynamic bending test method comprises the following steps: the bending was performed 20 ten thousand times under the conditions that the bending radius R was 3mm and the frequency was 30 times/min, and the results were observed.
In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.
Claims (4)
1. A transparent polyimide hardened film with low shrinkage, high hardness and high wear resistance is characterized in that: the hardening liquid for preparing the transparent polyimide hardening film consists of the following components in parts by weight:
50-80 parts of high-functionality polyurethane acrylate
10-20 parts of multifunctional polyether acrylate
10-20 parts of flexible monomer
10-20 parts of reactive diluent
0.5-2 parts of photoinitiator
0.05 to 0.2 portion of thermal initiator
80-150 parts of good solvent
2-20 parts of high-boiling point poor solvent
0.05-1 part of anti-fingerprint auxiliary agent
10-30 parts of inorganic nanoparticles;
the high-functionality polyurethane acrylate is a polyurethane modified acrylate oligomer with the functionality of not less than 6, and the multifunctional polyether acrylate is a polyether modified acrylate oligomer with the functionality of not less than 3;
the flexible monomer is polyether acrylate or polycaprolactone modified acrylate with single functionality or double functionality;
the polymerization degree of polyether or polycaprolactone in the polyether acrylate or polycaprolactone modified acrylate is 2-10;
the good solvent is one or more of PGM, IPA, BAC, MEK and MIBK, and the high-boiling point poor solvent is one or two of ethylene glycol and cyclohexanol;
the low-shrinkage high-hardness high-wear-resistance transparent polyimide hardened film is prepared by the following method:
(1) uniformly coating the hardening liquid on a transparent polyimide substrate, and then carrying out thermal drying and thermal curing;
(2) carrying out UV curing, then carrying out annealing treatment, cooling the hardened film, then attaching a protective film and slitting;
the thermal drying and thermal curing are carried out for 2-10min at the temperature of 100-160 ℃; the UV curing conditions are as follows: illumination intensity of 100-2Light amount of 300-2The temperature of the film surface is 40-60 ℃; the annealing treatment is carried out for 2-10min at the temperature of 120-180 ℃.
2. The low shrinkage, high hardness, high abrasion resistant transparent polyimide cured film according to claim 1, wherein: the active diluent is one or more of isobornyl methacrylate, tetrahydrofuran methyl acrylate, lauryl acrylate, isodecyl acrylate and polyethoxyethyl acrylate.
3. The low shrinkage, high hardness, high abrasion resistant transparent polyimide cured film according to claim 1, wherein: the photoinitiator is one or more of alpha-hydroxy ketone initiators and acetophenone initiators, the thermal initiator is one or more of peroxy thermal initiators and azo thermal initiators, the half-life period at 70 ℃ of the thermal initiator is not less than 10 hours, and the half-life period at 140 ℃ is not more than 5 minutes.
4. The low shrinkage, high hardness, high abrasion resistant transparent polyimide cured film according to claim 1, wherein: the fingerprint resisting agent is perfluoro vinyl ether reactive surfactant, and the inorganic nano particles are nano SiO2Or nano Al2O3。
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Families Citing this family (8)
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| CN112574609B (en) * | 2019-09-27 | 2023-04-07 | 新恒东薄膜材料（常州）有限公司 | High-wear-resistance anti-fingerprint auxiliary agent and preparation method and application thereof |
| CN110734698A (en) * | 2019-11-27 | 2020-01-31 | 上海金門量子科技有限公司 | hardening coating liquid for flexible cover plate |
| CN110885626B (en) * | 2019-12-13 | 2022-03-22 | 东风汽车集团有限公司 | Scratch-resistant fingerprint-resistant high-gloss piano black paint and preparation method and application thereof |
| CN111826079A (en) * | 2020-08-06 | 2020-10-27 | 宁波惠之星新材料科技有限公司 | Hardening liquid, flexible high-hardness high-wear-resistance cover plate hardening film, flexible high-hardness high-wear-resistance cover plate and preparation method thereof |
| CN114106379A (en) * | 2020-08-25 | 2022-03-01 | 新恒东薄膜材料（常州）有限公司 | Bending-resistant high-hardness high-wear-resistant polyester hardened film |
| CN112625290B (en) * | 2020-12-18 | 2024-01-16 | 深圳市华科创智技术有限公司 | Flexible display substrate |
| CN112708370B (en) * | 2020-12-28 | 2022-11-15 | 宁波长阳科技股份有限公司 | Anti-glare protective film and preparation method and application thereof |
| CN112694633A (en) * | 2021-01-22 | 2021-04-23 | 揭西鑫昌顺电子科技有限公司 | Multifunctional hardening film and method thereof |
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