CN116948523A - UV resin composition and application thereof - Google Patents

UV resin composition and application thereof Download PDF

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Publication number
CN116948523A
CN116948523A CN202310054212.7A CN202310054212A CN116948523A CN 116948523 A CN116948523 A CN 116948523A CN 202310054212 A CN202310054212 A CN 202310054212A CN 116948523 A CN116948523 A CN 116948523A
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Prior art keywords
compound
resin composition
parts
coating
polymerizable group
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CN202310054212.7A
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CN116948523B (en
Inventor
贾刚刚
丁兴立
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Beijing Tuofan Technology Co ltd
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Beijing Tuofan Technology Co ltd
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Priority to CN202310054212.7A priority Critical patent/CN116948523B/en
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    • GPHYSICS
    • G09EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09FDISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • G09F9/301Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements flexible foldable or roll-able electronic displays, e.g. thin LCD, OLED
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D183/00Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04Polysiloxanes
    • C09D183/06Polysiloxanes containing silicon bound to oxygen-containing groups
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D7/00Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40Additives
    • C09D7/60Additives non-macromolecular
    • C09D7/61Additives non-macromolecular inorganic
    • C09D7/62Additives non-macromolecular inorganic modified by treatment with other compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00Use of inorganic substances as compounding ingredients
    • C08K3/18Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20Oxides; Hydroxides
    • C08K3/22Oxides; Hydroxides of metals
    • C08K2003/2244Oxides; Hydroxides of metals of zirconium
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00Specific properties of additives
    • C08K2201/011Nanostructured additives

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Theoretical Computer Science (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • Inorganic Chemistry (AREA)
  • Inorganic Compounds Of Heavy Metals (AREA)
  • Paints Or Removers (AREA)

Abstract

The invention relates to the field of coatings, and discloses a UV resin composition and application thereof. The UV resin composition comprises a compound 1 and a compound 2, wherein the compound 1 is a compound with a trapezoid structure containing a polymerizable group; the compound 2 is nano metal zirconia particles modified by a polymerizable group. The coating is used for the surface layer of the flexible display, and plays roles of improving the light-emitting efficiency and protecting the display.

Description

UV resin composition and application thereof
Technical Field
The invention relates to the field of coatings, in particular to a UV resin composition and application thereof.
Background
The flexible display gradually enters the life of people after the flat panel display, and a larger market exists in the future. Compared with the inflexible display surface, the surface coating needs to improve the bending property on the basis of hardness and wear resistance, and for this purpose, the invention patent with publication number CN107207906A provides a solution, and the silane coupling agent with epoxy groups or acrylic groups is used for preparing the inorganic-organic hybrid material under alkaline conditions, so that the bending time is more than 20w times on the basis of meeting the hardness and wear resistance, and the purpose of protecting the display is achieved, but the light emitting efficiency is only 90-91%; for the solution of improving the transmittance of the display device, the patent publication No. WO2020106884A1 uses metal oxide nanoparticles modified by a polymerizable group to improve the refractive index of the coating by curing after printing, so as to improve the transmittance of the device, but the coating is positioned on the inner side of the component and does not have the functions of hardness and wear resistance.
Disclosure of Invention
The invention adopts the following specific scheme: a UV resin composition comprising a compound 1 and a compound 2, wherein the compound 1 is a compound having a trapezoid structure with a polymerizable group; the trapezoid structure is a structure containing a chemical formula 1;
chemical formula 1:
r1 and R2 are structural units containing polymerizable groups;
the compound 2 is nano zirconia particles modified by a polymerizable group.
The UV resin composition contains: 40-90 parts of compound 1;10-50 parts of compound 2;0.1-5 parts of initiator; 0.1-5 parts of flatting agent; 10-80 parts of a solvent; 0-50 parts of monomer diluent.
The UV resin composition is coated on the surface of the substrate by adopting a knife coating and spin coating mode, and is dried and then subjected to UV curing to form a film.
The UV resin composition is used for flexible display surfaces.
Compared with the prior art, the invention has the following beneficial effects:
the invention provides a UV resin composition and application thereof, wherein the UV resin composition comprises a compound 1 and a compound 2, the compound 1 is a compound with a trapezoid structure containing a polymerizable group, and the structure can meet the requirements of bending resistance, high hardness and high wear resistance; the compound 2 is nano zirconia particles with polymerizable groups, and the nano zirconia particles can improve the refractive index of the material, so that the light emitting efficiency of the display device is improved. The inorganic-organic hybrid material and the zirconia nano particles with the polymerization function are combined, and after the surface layer of the display is coated, the two requirements are simultaneously met, and the process is simplified.
Detailed Description
The present invention will be described below with reference to specific examples in order to make the objects, technical solutions and advantages of the present invention more apparent. It should be understood that the description is only illustrative and is not intended to limit the scope of the invention. In addition, in the following description, descriptions of well-known structures and techniques are omitted so as not to unnecessarily obscure the present invention.
The invention discloses a UV resin composition, which comprises a compound 1 and a compound 2, wherein the compound 1 is a compound with a trapezoid structure containing a polymerizable group; the trapezoid structure is a structure containing a chemical formula 1;
chemical formula 1:
r1 and R2 are polymerizable functional structural units containing epoxy groups, such as:and acrylic acid common polymerized units containing double bonds. The compound 2 is nano zirconia particles with polymerizable groups. The compound 2 is zirconia nano particles prepared by a high-temperature hydrothermal method, and the particle size of the zirconia nano particles is less than 10nm.
After the UV resin composition is cured, the UV resin composition comprises the following components in parts by weight: 40-90 parts of compound 1;10-50 parts of compound 2;0.1-5 parts of initiator; 0.1-5 parts of flatting agent; 0-50 parts of monomer diluent.
The monomer diluent is an acrylic acid monomer and epoxy monomer diluent; the acrylic monomer diluent is selected from acrylic monomers (e.g., SR423, SR238, CD421, TMPTA, DPHA) provided by the company sartomer; the epoxy monomer diluent is selected from mono-functional or multi-functional monomer diluents provided by the company, strong, such as TCM101, TCM201, TCM 104.
The initiator is a radical initiator and a cationic initiator such as organic phosphines such as biphenyl (2, 4, 6-trimethylbenzoyl) -phosphine oxide (TPO), irgacure 819 or Irgacure 184, itx, etc.; the cationic initiator is irgacure250, irgacure290, etc.
The leveling agent can be BYK 331, BYK 377, BYK 378, etc.
The solvent may be PGMEA, PGME, MIBK, and the appropriate ratio is selected according to the coating effect.
The UV resin composition of the invention is added with anti-fingerprint additives such as DAC-HP additives of KY-1203, KY-1271, RS-90 and DIC to improve the surface contact angle and the anti-fouling capability, and after the UV resin composition is cured, the parts of the anti-fingerprint additives are 0.1-2 parts by weight.
The resin composition is prepared by weighing the resin, the auxiliary agent, the initiator, the solvent and the like according to a certain proportion, and uniformly mixing by adopting a physical mixing method.
The UV resin composition is coated on the surface of the substrate by adopting a knife coating and spin coating mode, and is dried and then subjected to UV curing to form a film. The UV resin composition is used for the surface of a flexible display, improves the light-emitting efficiency and protects the display.
Preparation of Compound 1: reference patent CN107207906a for preparation
To be used forBy way of example, ladder compound 1 (ladder A) was synthesized
Adding 0.06g of potassium carbonate, 13.6g of water, 40g of tetrahydrofuran, stirring for 30min at room temperature, adding 30g of 2- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, stirring for 72h at room temperature, washing with water, and removing the solvent in vacuum to obtain resin A, wherein the molecular weight Mw is 7200 and Pd=2.0;
trapezoidal compound 2 (trapezoidal B) was prepared starting from 3- (methacryloyloxy) propyl trimethoxysilane
30g of 3- (methacryloxy) propyl trimethoxy silane, 40ml of tetrahydrofuran and 15g of water are added into a three-necked flask, the temperature is raised to 40-50 ℃, 1-2 drops of ammonia water are added, stirring is continued for 6 hours, water washing, drying and vacuum removal of the solvent are carried out, and colorless viscous resin B is obtained, wherein the molecular weight Mn=3500 and Pd=1.9.
Preparation of Compound 2
Reference is made to the patent: preparation of nano zirconia particles capable of being modified by polymeric groups through CN103328374A
Acrylic nanozirconia particles C
Under the protection of nitrogen, 30ml of benzyl alcohol and 0.08ml of water are added into a three-mouth bottle, and after stirring for 30min, N 2 Adding 4ml of zirconium isopropoxide under protection, stirring at high speed for 4 hours until the solution is clarified, transferring into an autoclave, heating to 250 ℃ for 15min, then heating to 15-325 ℃ every 3min, cooling to room temperature, and centrifuging to obtain the nano zirconium oxide crystal.
The nano zirconia crystal is soaked in 1N hydrochloric acid for 1h, filtered and washed to be neutral, KH570 (3- (methacryloyloxy) propyl trimethoxy silane) is added, the mass ratio is 3:1, the reaction is carried out for 2-3h at 80-150 ℃, centrifugal treatment is carried out, and acrylic modified nano zirconia particles C with the particle size of 5nm are obtained after drying.
The same protocol was used to prepare nano zirconium dioxide particles D containing an epoxy structure using KH 560.
The nano zirconia crystal is soaked in 1N hydrochloric acid for 1h, filtered and washed to be neutral, KH560 (3- (2, 3-glycidoxy) propyl trimethoxy silane) is added, the mass ratio is 3:1, the reaction is carried out for 2-3h at 80-150 ℃, centrifugal treatment is carried out, and epoxy group modified nano zirconia particles D with the particle size of 5nm are obtained after drying.
Preparation of UV compositions
Weighing and testing according to the parts recorded in the following table to obtain the product:
the blending proportion is as follows:
the testing method comprises the following steps:
blending according to the proportion in the table, coating on a PET substrate, baking at 100 ℃ for 1min, and then performing UV curing for 2s at 1000mw/s to obtain a flat coating for testing;
hardness: pencil hardness tester
Wear-resistant: the reciprocating friction tester is 2cm X2 cm, #0000 steel wool, 1000 times, wherein V indicates no change in appearance of the coating, the requirement is met, and X indicates scratch on the appearance of the coating;
transmittance: ULTRASCAN VIS
Number of bending times: the bending tester has an inner bending radius of 1.5mm and bending times of 200000 times, V represents no crack meeting the requirement, and X represents a crack with a coating or burst of the coating;
the test data after coating are as follows:
example 1 Example 2 Example 3 Comparative example 1 Comparative example 2
Hardness: 4H 4H 4H 5H H
wear-resistant: V V V V X
transmittance: 97% 98% 97% 90% 99%
number of bending times: V V V V X
from the experimental data, the resin added with compound 1 and compound 2 simultaneously has better performance than the resin added with one alone. The invention adopts the modifiable nano zirconia particles and the inorganic-organic hybrid material to prepare the UV composition, and achieves the purposes of improving the light-emitting efficiency and protecting the flexible display after curing.
The foregoing description is only one specific embodiment of the present invention, but the specific protection scope of the present invention is not limited to the foregoing description, and any simple substitution or modification within the scope of the technical idea disclosed in the present invention and according to the technical scheme of the present invention should be within the protection scope of the present invention.

Claims (4)

1. A UV resin composition, wherein the UV resin composition comprises a compound 1 and a compound 2, and the compound 1 is a compound with a trapezoid structure containing a polymerizable group; the trapezoid structure is a structure containing a chemical formula 1;
chemical formula 1:
r1 and R2 are structural units containing polymerizable groups;
the compound 2 is nano zirconia particles modified by a polymerizable group.
2. The UV resin composition according to claim 1 or 2, wherein the UV resin composition comprises: 40-90 parts of compound 1;10-50 parts of compound 2;0.1-5 parts of initiator; 0.1-5 parts of flatting agent; 10-80 parts of a solvent; 0-50 parts of monomer diluent.
3. The UV resin composition according to claim 1, wherein the UV resin composition is coated on the surface of the substrate by blade coating or spin coating, and is dried and then UV cured to form a film.
4. Use of the UV resin composition according to any one of claims 1-3, wherein the UV resin composition is used for flexible display surfaces.
CN202310054212.7A 2023-02-03 2023-02-03 UV resin composition and application thereof Active CN116948523B (en)

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Application Number Priority Date Filing Date Title
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CN116948523B CN116948523B (en) 2024-05-03

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101361011A (en) * 2005-11-05 2009-02-04 3M创新有限公司 Optical films comprising high refractive index and antireflective coatings
CN107207906A (en) * 2014-12-31 2017-09-26 可隆工业株式会社 For the resin combination of hard conating and including hard coat film of its cured form as coating
CN107406690A (en) * 2015-04-21 2017-11-28 株式会社大赛璐 Resin composite for forming hard coat layer and its solidfied material
CN109749017A (en) * 2017-11-03 2019-05-14 宁波激智科技股份有限公司 A kind of composition and a kind of brightness enhancement film
CN109943226A (en) * 2019-03-20 2019-06-28 深圳市航天新材科技有限公司 A kind of high class glass masking liquid composition resistant to bending and preparation method thereof
CN111971174A (en) * 2018-04-26 2020-11-20 富士胶片株式会社 Hard coat film, article provided with hard coat film, and image display device
CN112940617A (en) * 2021-01-28 2021-06-11 耿少卿 Ultrathin glass coating material, construction method, impact-resistant layer structure and electronic equipment

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101361011A (en) * 2005-11-05 2009-02-04 3M创新有限公司 Optical films comprising high refractive index and antireflective coatings
CN107207906A (en) * 2014-12-31 2017-09-26 可隆工业株式会社 For the resin combination of hard conating and including hard coat film of its cured form as coating
CN107406690A (en) * 2015-04-21 2017-11-28 株式会社大赛璐 Resin composite for forming hard coat layer and its solidfied material
CN109749017A (en) * 2017-11-03 2019-05-14 宁波激智科技股份有限公司 A kind of composition and a kind of brightness enhancement film
CN111971174A (en) * 2018-04-26 2020-11-20 富士胶片株式会社 Hard coat film, article provided with hard coat film, and image display device
CN109943226A (en) * 2019-03-20 2019-06-28 深圳市航天新材科技有限公司 A kind of high class glass masking liquid composition resistant to bending and preparation method thereof
CN112940617A (en) * 2021-01-28 2021-06-11 耿少卿 Ultrathin glass coating material, construction method, impact-resistant layer structure and electronic equipment

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