CN110591544A - High-hardness and low-haze UV hardened layer coating liquid - Google Patents

High-hardness and low-haze UV hardened layer coating liquid Download PDF

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Publication number
CN110591544A
CN110591544A CN201910925846.9A CN201910925846A CN110591544A CN 110591544 A CN110591544 A CN 110591544A CN 201910925846 A CN201910925846 A CN 201910925846A CN 110591544 A CN110591544 A CN 110591544A
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acrylate
parts
poss
benzoic acid
bismaleimide
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CN110591544B (en
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郑婷
陈善勇
许显成
巫柯
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Sichuan Yu Xixin Materials Ltd By Share Ltd
Sichuan University
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Sichuan Yu Xixin Materials Ltd By Share Ltd
Sichuan University
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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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/10—Transparent films; Clear coatings; Transparent materials

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

The invention discloses a high-hardness and low-haze UV hardening layer coating liquid which comprises POSS polymaleimide, an acrylate prepolymer, an acrylate monomer, a photoinitiator, a leveling agent and a solvent; the POSS polymaleimide is prepared from chloropropyl POSS and bismaleimide benzoic acid. After the coating liquid is adopted to coat the optical film, crystal points are not formed on the surface of the film, the hardness of the film can be obviously improved, and the mechanical property of the optical film is improved; meanwhile, the optical performance of the optical film is not affected, and the use requirement of the optical film in special occasions can be met.

Description

High-hardness and low-haze UV hardened layer coating liquid
Technical Field
The invention belongs to the technical field of functional coatings, and particularly relates to a high-hardness and low-haze UV hardened layer coating liquid.
Background
Optical films have a wide range of applications in life, such as touch screens, display screens. The optical film generally has the problems of poor stability, poor friction resistance and the like, and a hardening layer is a common processing mode for coating the optical film, and the hardening layer can play a role in hardening and scratch-resistant protection. The UV-cured acrylic resin is the most common hardening liquid component, and can be directly used in occasions with low hardness requirements. However, in order to further increase the hardness, inorganic nanoparticles, particularly silicon nanoparticles, are often added to the resin. Optical hardening films often require that the surface of the film not have "crystalline spots" while having high light transmittance and low haze. Although the addition of the inorganic nanoparticles can provide hardness, the inorganic nanoparticles have poor compatibility with resin, and after a hardening liquid composed of the inorganic nanoparticles and the resin forms a hardened film, the hardness can meet the requirement, but the problems of low transparency, high haze and the like exist.
Disclosure of Invention
The invention aims to solve the technical problem of the prior art and provides a hardened layer coating liquid, and an optical hardened film formed by coating the hardened layer coating liquid has higher hardness (up to 6H), higher light transmittance and low haze (less than or equal to 1).
In order to achieve the purpose, the invention adopts the technical scheme that: the invention provides a high-hardness and low-haze UV hardening layer coating liquid, which comprises the following components in parts by mass: 5-20 parts of POSS polymaleimide, 20-60 parts of acrylate prepolymer, 10-40 parts of acrylate monomer, 0.5-3 parts of photoinitiator, 0.1-2 parts of flatting agent and 20-60 parts of solvent; the POSS polymaleimide is prepared from chloropropyl POSS and bismaleimide benzoic acid, and the raw materials chloropropyl POSS and bismaleimide benzoic acid have the following structural characteristics:
the bismaleimide benzoic acid is any one selected from 2, 6-bismaleimide benzoic acid, 2, 5-bismaleimide benzoic acid, 2, 4-bismaleimide benzoic acid, 2, 3-bismaleimide benzoic acid, 3, 6-bismaleimide benzoic acid, 3, 5-bismaleimide benzoic acid and 3, 4-bismaleimide benzoic acid.
The number of maleimide groups introduced into the POSS polymaleimide molecule is determined by the molar ratio of bismaleimide benzoic acid to chloropropyl POSS, theoretically, 1mol of chloropropyl POSS can react with 8mol of bismaleimide benzoic acid at most, and the reaction formula is as follows:
the preparation method of POSS polymaleimide comprises the following steps: dissolving chloropropyl POSS and bismaleimide benzoic acid in a proper amount of solvent according to a molar ratio of 1: 4-9, adding anhydrous potassium carbonate, wherein the molar ratio of the added anhydrous potassium carbonate to chloropropyl POSS is 10:1, refluxing for 8 hours under the protection of nitrogen, cooling, filtering, and distilling the solvent under reduced pressure to obtain a solid POSS polymaleimide. The solvent is selected from any one of toluene, ethyl acetate, dichloroethane, dioxane and absolute ethyl alcohol.
On the basis of the technical scheme, the invention can be further improved as follows.
Further, the acrylate monomer is selected from one or more of 2-phenoxyethyl acrylate, isobornyl acrylate, cyclohexanol acrylate, 1, 6-hexanediol diacrylate, dipropylene glycol diacrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, isooctyl acrylate, butyl acrylate, ethyl acrylate, tripropylene glycol acrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate, and dipentaerythritol hexaacrylate.
Further, the acrylate prepolymer is a combination of polyurethane acrylic resins having 4 to 9 acrylate functional groups.
Further, the photoinitiator is selected from any one of Irgacure 184, Irgacure 1173, Irgacure 651, Irgacure 500, and Irgacure 819.
Further, the solvent is toluene, ethyl acetate, butyl acetate, acetone or 2-butanone, preferably ethyl acetate.
The invention has the beneficial effects that:
in order to improve the hardness performance of the acrylic resin transparent coating, octafunctional chloropropyl POSS, 4-9 functional acrylate prepolymer, acrylate monomer, photoinitiator, flatting agent and the like are blended to prepare a coating liquid, and after the coating liquid is coated on an optical film, a hardened film can be formed on the surface of the film by strong light irradiation. Because the coating liquid does not contain inorganic nano particles, a hardened layer formed on the surface of the film does not have crystal points, the light transmittance and the haze of the optical film are not changed greatly, and the optical performance is ensured; and the hardness of the formed hardened layer is between 3H and 6H, so that the optical film can be effectively protected, and the mechanical property of the optical film is improved.
Detailed Description
Preparation of POSS polymaleimide
The preparation reaction formula of the POSS polymaleimide used in the invention is shown as the formula (1-1):
the preparation process comprises the following steps:
s1: dissolving chloropropyl POSS and bismaleimide benzoic acid in a solvent according to a molar ratio of 1: 4-9, adding anhydrous potassium carbonate, and uniformly stirring to obtain a reaction solution; the molar ratio of the added anhydrous potassium carbonate to the chloropropyl POSS is 10: 1; the bismaleimide benzoic acid is any one of 2, 6-bismaleimide benzoic acid, 2, 5-bismaleimide benzoic acid, 2, 4-bismaleimide benzoic acid, 2, 3-bismaleimide benzoic acid, 3, 6-bismaleimide benzoic acid, 3, 5-bismaleimide benzoic acid and 3, 4-bismaleimide benzoic acid; the solvent is selected from toluene, ethyl acetate, dichloroethane, dioxane or absolute ethyl alcohol;
s2: and (3) placing the reaction liquid in a reaction container, refluxing for 8 hours under the protection of nitrogen, cooling, filtering, and then decompressing and evaporating the solvent to obtain a solid, namely POSS polymaleimide.
The following examples are provided to illustrate specific embodiments of the present invention.
The first embodiment is as follows:
the coating liquid in the embodiment is prepared by the following steps:
1mol part of chloropropyl POSS is dissolved in a proper amount of toluene, 8mol parts of 3, 5-bismaleimide benzoic acid is added, and 10 mol parts of anhydrous potassium carbonate is added. And (3) under the protection of nitrogen, refluxing for 8h, cooling, filtering, collecting filtrate, and evaporating the solvent under reduced pressure to obtain a white solid, namely POSS polymaleimide.
And (2) uniformly stirring 5 parts by mass of the POSS polymaleimide, 35 parts by mass of hexafunctional group urethane acrylate, 10 parts by mass of trimethylolpropane triacrylate, 0.5 part by mass of Irgacure 184, 0.15 part by mass of BYK 333 and 50 parts by mass of ethyl acetate in a reaction kettle at room temperature to obtain the coating liquid.
Example two:
the coating liquid in the embodiment is prepared by the following steps:
1mol part of chloropropyl POSS is dissolved in a proper amount of toluene, 9 mol parts of 2, 6-bismaleimide benzoic acid are added, and 10 mol parts of anhydrous potassium carbonate are added. And (3) under the protection of nitrogen, refluxing for 8h, cooling, filtering, collecting filtrate, and evaporating the solvent under reduced pressure to obtain a white solid, namely POSS polymaleimide.
Taking 10 parts by mass of POSS polymaleimide, 20 parts by mass of octafunctional polyurethane acrylate, 40 parts by mass of tripropylene glycol acrylate, 1 part by mass of Irgacure 1173, 0.5 part by mass of BYK 333 and 40 parts by mass of butyl acetate, and uniformly stirring at room temperature in a reaction kettle to obtain the coating liquid.
Example three:
the coating liquid in the embodiment is prepared by the following steps:
1mol part of chloropropyl POSS is dissolved in a proper amount of toluene, 6 mol parts of 2, 5-bismaleimide benzoic acid are added, and 10 mol parts of anhydrous potassium carbonate are added. And (3) under the protection of nitrogen, refluxing for 8h, cooling, filtering, collecting filtrate, and evaporating the solvent under reduced pressure to obtain a white solid, namely POSS polymaleimide.
Taking 15 parts by mass of the POSS polymaleimide, 40 parts by mass of pentafunctional group-polymerized urethane acrylate, 20 parts by mass of hydroxyethyl acrylate, 2 parts by mass of Irgacure 651, 1 part by mass of BYK 333 and 60 parts by mass of toluene, and uniformly stirring at room temperature in a reaction kettle to obtain the coating liquid.
Example four:
the coating liquid in the embodiment is prepared by the following steps:
1mol part of chloropropyl POSS is dissolved in a proper amount of toluene, 8mol parts of 2, 3-bismaleimide benzoic acid are added, and 10 mol parts of anhydrous potassium carbonate are added. And (3) under the protection of nitrogen, refluxing for 8h, cooling, filtering, collecting filtrate, and evaporating the solvent under reduced pressure to obtain a white solid, namely POSS polymaleimide.
And (2) uniformly stirring 20 parts by mass of POSS polymaleimide, 60 parts by mass of tetrafunctional group polyurethane acrylate, 10 parts by mass of butyl acrylate, 3 parts by mass of Irgacure 819, 2 parts by mass of BYK 333 and 60 parts by mass of acetone in a reaction kettle at room temperature to obtain the coating liquid.
Example five:
the coating liquid in the embodiment is prepared by the following steps:
1mol part of chloropropyl POSS is dissolved in a proper amount of toluene, 9 mol parts of 3, 4-bismaleimide benzoic acid is added, and 10 mol parts of anhydrous potassium carbonate is added. And (3) under the protection of nitrogen, refluxing for 8h, cooling, filtering, collecting filtrate, and evaporating the solvent under reduced pressure to obtain a white solid, namely POSS polymaleimide.
Taking 10 parts by mass of the POSS polymaleimide, 40 parts by mass of nine-functional group urethane acrylate, 20 parts by mass of dipropylene glycol diacrylate, 0.5 part by mass of Irgacure 819, 0.5 part by mass of BYK 333 and 50 parts by mass of ethyl acetate, and uniformly stirring at room temperature in a reaction kettle to obtain the coating liquid.
Example six:
the coating liquid in the embodiment is prepared by the following steps:
1mol part of chloropropyl POSS is dissolved in a proper amount of toluene, 6 mol parts of 2, 4-bismaleimide benzoic acid are added, and 10 mol parts of anhydrous potassium carbonate are added. And (3) under the protection of nitrogen, refluxing for 8h, cooling, filtering, collecting filtrate, and evaporating the solvent under reduced pressure to obtain a white solid, namely POSS polymaleimide.
Taking 10 parts by mass of the POSS polymaleimide, 20 parts by mass of octafunctional agglomerated urethane acrylate, 20 parts by mass of 1, 6-hexanediol diacrylate, 1 part by mass of Irgacure 184, 1 part by mass of BYK 333 and 50 parts by mass of ethyl acetate, and uniformly stirring at room temperature in a reaction kettle to obtain the coating liquid.
Analysis of results
The high-hardness and low-haze UV curing layer coating liquid obtained in examples 1 to 6 was uniformly coated on a high-transparency polyester film (transmittance: more than 90% and haze: 1), dried in an oven at 80 ℃ for 2 minutes, and then cured by irradiation with a 160W high-pressure mercury lamp to obtain a cured film having a film thickness of 2 to 3 μm.
And (3) testing pencil hardness: the test was carried out by pencil scratching the film according to the method specified in the standard GB/T6739-1996.
Light transmittance and haze test: the total light transmittance (T) and haze (H) were measured using a haze meter (color haze meter HSP-150Vis in Japan). The test results are shown in table 1.
TABLE 1 coating hardness and transmittance (T) and haze test (H)
Hardening liquid Hardness of Transmittance (T) Haze (H)
Example one 3H 92％ 0.91
Example two 4H 92％ 0.91
EXAMPLE III 5H 91％ 0.92
Example four 6H 91％ 0.95
EXAMPLE five 4H 92％ 0.91
EXAMPLE six 3H 92％ 0.91
As can be seen from the table, after the coating liquid of the invention is coated on a high-transparency polyester film, the hardness of the film is obviously increased, and the light transmittance and the haze are not obviously reduced, which shows that the coating liquid of the invention can improve the hardness of the optical film and can not influence the optical performance of the film.
While the present invention has been described in detail with reference to the embodiments, it should not be construed as limited to the scope of the patent. Various modifications and changes may be made by those skilled in the art without inventive step within the scope of the appended claims.

Claims (9)

1. The high-hardness and low-haze UV hardening layer coating liquid is characterized by comprising the following components in parts by mass: 5-20 parts of POSS polymaleimide, 20-60 parts of acrylate prepolymer, 10-40 parts of acrylate monomer, 0.5-3 parts of photoinitiator, 0.1-2 parts of flatting agent and 20-60 parts of solvent; the POSS polymaleimide is prepared from chloropropyl POSS and bismaleimide benzoic acid, wherein the structures of the chloropropyl POSS and the bismaleimide benzoic acid are respectively shown as a formula (I) and a formula (II):
wherein R is-CH2CH2CH2Cl; the maleimide benzoic acid is any one of 2, 6-bismaleimide benzoic acid, 2, 5-bismaleimide benzoic acid, 2, 4-bismaleimide benzoic acid, 2, 3-bismaleimide benzoic acid, 3, 6-bismaleimide benzoic acid, 3, 5-bismaleimide benzoic acid and 3, 4-bismaleimide benzoic acid.
2. The high-hardness, low-haze UV-hardening layer coating liquid as set forth in claim 1, characterized by comprising the following components in parts by mass: 5 parts of POSS polymaleimide, 35 parts of acrylate prepolymer, 10 parts of acrylate monomer, 0.5 part of photoinitiator, 0.15 part of flatting agent and 50 parts of solvent.
3. The high-hardness, low-haze UV-curable layer coating liquid according to claim 1, wherein the POSS polymaleimide is prepared by:
s1: dissolving chloropropyl POSS and bismaleimide benzoic acid in a solvent according to a molar ratio of 1: 4-9, adding anhydrous potassium carbonate, and uniformly stirring to obtain a reaction solution; the molar ratio of the added anhydrous potassium carbonate to the chloropropyl POSS is 10: 1; the solvent is toluene, ethyl acetate, dichloroethane, dioxane or absolute ethyl alcohol;
s2: and (3) placing the reaction liquid in a reaction container, refluxing for 8 hours under the protection of nitrogen, cooling, filtering, and then decompressing and evaporating the solvent to obtain a solid, namely POSS polymaleimide.
4. The high-hardness, low-haze UV-hardening layer coating liquid as set forth in claim 3, wherein: in S1, the mol ratio of chloropropyl POSS to bismaleimide benzoic acid is 1: 8.
5. The high-hardness, low-haze UV-hardening layer coating liquid as set forth in claim 1, wherein: the acrylate monomer is one or more of 2-phenoxyethyl acrylate, isobornyl acrylate, cyclohexanol acrylate, 1, 6-hexanediol diacrylate, dipropylene glycol diacrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, isooctyl acrylate, butyl acrylate, ethyl acrylate, tripropylene glycol acrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate and dipentaerythritol hexaacrylate.
6. The high-hardness, low-haze UV-hardening layer coating liquid as set forth in claim 1, wherein: the acrylate prepolymer is polyurethane propylene resin with 4-9 acrylate functional groups.
7. The high-hardness, low-haze UV-hardening layer coating liquid as set forth in claim 1, wherein: the photoinitiator is any one of Irgacure 184, Irgacure 1173, Irgacure 651, Irgacure 500 and Irgacure 819.
8. The high-hardness, low-haze UV-hardening layer coating liquid as set forth in claim 1, wherein: the solvent is toluene, ethyl acetate, butyl acetate, acetone or 2-butanone.
9. The method for preparing a high-hardness, low-haze UV-curable layer coating liquid according to any one of claims 1 to 8, which comprises: and adding the POSS polymaleimide, the acrylate prepolymer, the acrylate monomer, the photoinitiator, the leveling agent and the solvent into a reaction container according to the mass ratio, and stirring uniformly at room temperature to obtain the coating liquid.
CN201910925846.9A 2019-09-27 2019-09-27 High-hardness and low-haze UV hardened layer coating liquid Active CN110591544B (en)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101597382A (en) * 2009-06-29 2009-12-09 杭州博纳特光电科技有限公司 A kind of method for preparing transparent hardening coat in plastic sheet surface
US20110312098A1 (en) * 2010-05-19 2011-12-22 Zyvex Performance Materials System and method of assessing nanotube purity
CN104199128A (en) * 2014-08-21 2014-12-10 昆山乐凯锦富光电科技有限公司 Optical hardening film
CN104559701A (en) * 2014-12-29 2015-04-29 宁波大榭开发区综研化学有限公司 Anti-newton-ring and anti-fouling coating composition, hardened film and preparation method
CN105086449A (en) * 2015-09-11 2015-11-25 西北工业大学 Phosphorus-containing POSS (polyhedral oligomeric silsesquioxane) flame-retardant bismaleimide resin and preparation method thereof
CN106750459A (en) * 2016-12-14 2017-05-31 合肥乐凯科技产业有限公司 One kind can print two-sided cured film

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101597382A (en) * 2009-06-29 2009-12-09 杭州博纳特光电科技有限公司 A kind of method for preparing transparent hardening coat in plastic sheet surface
US20110312098A1 (en) * 2010-05-19 2011-12-22 Zyvex Performance Materials System and method of assessing nanotube purity
CN104199128A (en) * 2014-08-21 2014-12-10 昆山乐凯锦富光电科技有限公司 Optical hardening film
CN104559701A (en) * 2014-12-29 2015-04-29 宁波大榭开发区综研化学有限公司 Anti-newton-ring and anti-fouling coating composition, hardened film and preparation method
CN105086449A (en) * 2015-09-11 2015-11-25 西北工业大学 Phosphorus-containing POSS (polyhedral oligomeric silsesquioxane) flame-retardant bismaleimide resin and preparation method thereof
CN106750459A (en) * 2016-12-14 2017-05-31 合肥乐凯科技产业有限公司 One kind can print two-sided cured film

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