CN112011276B - UV curing adhesive-based polarizing plate and preparation method thereof - Google Patents

UV curing adhesive-based polarizing plate and preparation method thereof Download PDF

Info

Publication number
CN112011276B
CN112011276B CN202010928766.1A CN202010928766A CN112011276B CN 112011276 B CN112011276 B CN 112011276B CN 202010928766 A CN202010928766 A CN 202010928766A CN 112011276 B CN112011276 B CN 112011276B
Authority
CN
China
Prior art keywords
compound
polarizing plate
methyl
adhesive
phenyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN202010928766.1A
Other languages
Chinese (zh)
Other versions
CN112011276A (en
Inventor
孟允
韩建伟
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shandong Taitel New Material Technology Co ltd
Original Assignee
Shandong Taitel New Material Technology Co ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shandong Taitel New Material Technology Co ltd filed Critical Shandong Taitel New Material Technology Co ltd
Priority to CN202010928766.1A priority Critical patent/CN112011276B/en
Publication of CN112011276A publication Critical patent/CN112011276A/en
Application granted granted Critical
Publication of CN112011276B publication Critical patent/CN112011276B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • 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
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • 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
    • C08J7/12—Chemical modification
    • C08J7/14—Chemical modification with acids, their salts or anhydrides
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • 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
    • C08J2329/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Derivatives of such polymer
    • C08J2329/02—Homopolymers or copolymers of unsaturated alcohols
    • C08J2329/04—Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Polarising Elements (AREA)

Abstract

The invention discloses a UV curing adhesive-based polarizing plate and a preparation method thereof, wherein the UV curing adhesive is coated on one surface of an optical film and then covered with a polarizer; and then ultraviolet light is cured to obtain the polarizing plate. The adhesive can fully cure epoxy compounds and (methyl) acrylate compounds, does not reduce the bonding strength, can prevent the transparency of an adhesive layer from being reduced, and also reduces the overflow of an initiator; the compound formed after the hybrid curing of the adhesive provided by the invention contains carboxyl, can be firstly combined with moisture in a high humidity environment, and solves the problem that in the high humidity environment in the prior art, hydroxyl groups existing on the surface of a polyvinyl alcohol (PVA) film are preferentially combined with moisture hydrogen bonds rather than with the hydrogen bonds of the free radical curable adhesive composition, so that the adhesiveness of the free radical curable adhesive composition is reduced.

Description

UV curing adhesive-based polarizing plate and preparation method thereof
Technical Field
The invention relates to a UV curing adhesive-based polarizing plate.
Background
The traveling direction of the light wave is perpendicular to the electric field and the magnetic field, and the electric field and the magnetic field components of the light wave are also perpendicular to each other, that is, the traveling direction, the electric field and the magnetic field components are parallel to each other. The polarizer blocks the component perpendicular to the polarizer and allows only the component parallel to the polarizer to pass through. So if one of the polarizing plates is held up to look toward a light source, the light becomes darker, but if the two polarizing plates are stacked, it is not the same. Rotating the relative angles of the two polarizing plates, it is found that the brightness of light becomes darker and darker with the difference of the relative angles; when the barrier angles of the two polarizers are perpendicular to each other, the light can not pass through the two polarizers at all. An adhesive is important as an important raw material of a polarizing plate, and a conventional cation-curable adhesive has high adhesion to various films and heat resistance, but dark polymerization (delayed curing) occurs, so that a cured product of the adhesive is liable to be subjected to curling deformation when stored in the form of a roll. In addition, the polarizing plate may cause severe light leakage under more severe conditions than wet heat (e.g., warm water immersion at 60 ℃).
Disclosure of Invention
The invention aims to provide a UV curing adhesive-based polarizing plate, which adopts a UV curing adhesive with high curing speed, strong humidity and heat resistance and high adhesive strength.
The UV curable adhesive-based polarizing plate of the present invention has an effect of high adhesive strength to all of a triacetyl cellulose (TAC) film, a polyethylene terephthalate (PET) film, and a cycloolefin polymer (COP) film.
The invention adopts the following technical scheme:
a UV curing adhesive-based polarizing plate comprises a polarizer, an optical film and a UV curing adhesive positioned between the polarizer and the optical film; a UV-curable adhesive for polarizing plates, comprising: 40 to 90 parts by weight of an epoxy compound; 10 to 50 parts by weight of a (meth) acrylate compound; 1 to 20 parts by weight of a vinyl ether compound; 1 to 20 parts by weight of a carboxylic acid compound containing an unsaturated double bond; 0.01-10 parts by weight of a cationic photoinitiator; 0.01-10 parts by weight of a free radical photoinitiator.
The preparation method of the UV curing adhesive-based polarizing plate comprises the steps of mixing an epoxy compound, a (methyl) acrylate compound, a vinyl ether compound, a carboxylic acid compound containing unsaturated double bonds, a cationic photoinitiator and a free radical photoinitiator to obtain the UV curing adhesive; compounding the polarizer, the optical film and the UV curing adhesive to obtain a polarizing plate; specifically, a UV curing adhesive is coated on one surface of the optical film, and then a polarizer is covered; and then uv-cured to obtain a polarizing plate.
According to the general knowledge, the polarizing plate has a laminated structure, an optical film is adhered to one surface of a polarizer formed of a polyvinyl alcohol (PVA) -based resin, which is generally dyed with dichroic dyes or iodine, using an adhesive, and triacetyl cellulose (TAC) -based film, polyethylene terephthalate (PET) film, Cyclic Olefin Polymer (COP) film are mainly used as the optical film of the polarizing plate. The polaroid and the optical film related to the invention are all existing products.
In the present invention, the epoxy compound includes alicyclic epoxy compounds and aromatic epoxy compounds, wherein the alicyclic epoxy compound includes bifunctional alicyclic epoxy compounds, and may further include monofunctional alicyclic epoxy compounds and trifunctional or higher alicyclic epoxy compounds; aromatic epoxy compounds include polyglycidyl ethers of aromatic compounds, including polyglycidyl ethers prepared from aromatic compounds having at least two hydroxyl groups.
Further, the alicyclic epoxy group means epoxidized C3～C20Alicyclic group of (2), containing an epoxide group C3～C20C of a cycloaliphatic radical2～C20Alicyclic radicals, or containing epoxidised C3～C20C of a cycloaliphatic radical of1～C10Alkyl group of (1). Further, the alicyclic epoxy resin contains at least one of an epoxycyclohexyl group, an epoxycyclopentyl group and a glycidyl ether group, for example, the bifunctional alicyclic epoxy compound may contain epoxycyclohexylmethyl epoxycyclohexanecarboxylate, alkylene glycol epoxycyclohexanecarboxylate, dicarboxylic acid-epoxycyclohexylmethyl ester, polyethylene glycol epoxycyclohexylmethyl ether, alkylene glycol epoxycyclohexylmethyl ether, diepoxyltrirocyclic compound, diepoxymspirospirocyclic compound, vinylcyclohexene diepoxide, epoxycyclopentylether and diepoxycyclodecane compound, may be 3, 4-epoxycyclohexylmethyl 3, 4-epoxy-6-methylcyclohexylmethyl-3 ',4' -epoxy-6 ' -methylcyclohexanecarboxylate, at least one of bis (3, 4-epoxy-6-methylcyclohexyl) adipate and 3, 4-epoxycyclohexylmethyl-3 ',4' -epoxycyclohexanecarboxylate-modified epsilon-caprolactone; further, the polyglycidyl ether of an aromatic compound may comprise at least one selected from the group consisting of polyglycidyl ethers of monohydroxyphenols having at least one aromatic ring (e.g., phenol, cresol, and butylphenol), or alkylene oxide adducts thereof, for example, glycidyl ethers of bisphenol a, bisphenol F, or epoxy novolac resins, or alkylene oxide adducts thereof; polyglycidyl ethers of aromatic compounds having at least two phenolic hydroxyl groups (e.g., resorcinol, hydroquinone, or catechol); polyglycidyl ethers of aromatic compounds having at least two alcoholic hydroxyl groups (e.g., benzenedimethanol, benzenediethanol, or benzenedibutanol); polyacids with at least two carboxylic acid groupsGlycidyl esters of aromatic-like compounds (e.g., phthalic acid, terephthalic acid, or trimellitic acid); glycidyl esters of benzoic acid (e.g., benzoic acid, toluic acid, and naphthoic acid); styrene oxide; and the epoxide of divinylbenzene.
The epoxy compound composed of the alicyclic epoxy compound and the aromatic epoxy compound employed in the present invention has a higher glass transition temperature in a homopolymer phase to improve durability by supporting a stacked structure of the polarizer, the adhesive layer, and the optical film, and can increase interfacial adhesiveness between the polarizer and the optical film by securing chemical bonding and intermediate wettability through hydroxyl groups generated during the reaction, the adhesive can improve durability and interfacial adhesion between the polarizer and the optical film, and can prevent cracks from being generated in the polarizer upon thermal shock. The polyglycidyl ether and (meth) acrylate compound all exhibited medium water resistance and adhesive strength for films comprising triacetyl cellulose (TAC) film, polyethylene terephthalate (PET) film, and cycloolefin polymer (COP) film. In addition, the polyglycidyl ether can prevent a rapid increase in the viscosity and reaction speed of the adhesive caused by the bifunctional alicyclic epoxy compound.
In the present invention, the (meth) acrylate compound includes a bifunctional (meth) acrylate compound; may be a monoalkyl glycol difunctional (meth) acrylate compound or a polyalkylene glycol difunctional (meth) acrylate compound such as at least one of dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate and triethylene glycol di (meth) acrylate, for example, the difunctional (meth) acrylate compound may be hexanediol di (meth) acrylate, but is not limited thereto. The bifunctional (meth) acrylate compound does not deteriorate the curing reaction by moisture, can perform a stable photo-curing reaction, and in addition, has a high curing rate, and can enhance the adhesive strength between the polarizer and the optical film by coupling with epoxy compound chain migration during curing.
In the present invention, the vinyl ether compound includes at least one of diethylene glycol monovinyl ether, 4-hydroxybutyl vinyl ether, 1, 4-butanediol vinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, t-butyl vinyl ether, (vinyloxy) -2, 2-bis ((vinyloxy) methyl) butane, 1, 3-bis (vinyloxy) -2, 2-bis ((vinyloxy) methyl) propane, and cyclohexyl vinyl ether; the lone electron pair on the oxygen atom of the vinyl ether compound is conjugated with the carbon-carbon double bond, so that the electron cloud density of the double bond is increased, an electron-rich double bond is formed, the reaction activity is high, and free radical polymerization, cationic polymerization and charge transfer compound crosslinking copolymerization can be carried out. In addition, hydrogen bonds between hydroxyl groups contained in the cured adhesive composition and hydroxyl groups present on the surface of the polyvinyl alcohol-based film increase the adhesive strength between the adhesive and the polyvinyl alcohol-based film.
In the present invention, the carboxylic acid compound containing an unsaturated double bond includes at least one of maleic acid, fumaric acid, 2-methyl-2-butenoic acid, and trans-2-methyl-2-butenoic acid. The cationic photoinitiator may comprise: any one or combination of diaryl iodonium salt, triaryl sulfonium salt and arylcyclopentadienyl iron salt compound, specifically selected from diphenyl-4- (phenylthio) phenyl sulfonium hexafluorophosphate, (4-hydroxyphenyl) methylbenzyl sulfonium tetrakis (pentafluorophenyl) borate, 4- (4-biphenylthio) phenyl-4-biphenylphenyl sulfonium tetrakis (pentafluorophenyl) borate, 4- (phenylthio) phenyl diphenyl sulfonium phenyl tris (pentafluorophenyl) borate, [4- (4-biphenylthio) phenyl ] -4-biphenylphenyl sulfonium phenyl tris (pentafluorophenyl) borate, diphenyl [4- (phenylthio) phenyl ] sulfonium tris (pentafluoroethyl) trifluoro phosphate, diphenyl [4- (phenylthio) phenyl ] sulfonium tetrakis (pentafluorophenyl) borate, and salt of aryl cyclopentadienyl iron salt, Any one or combination of more of diphenyl [4- (phenylthio) phenyl ] sulfonium hexafluorophosphate, 4- (4-diphenylthio) phenyl-4-biphenylphenyl sulfonium tris (pentafluoroethyl) trifluorophosphate, bis [4- (diphenylsulfonium) phenyl ] thioether phenyl tris (pentafluorophenyl) borate, [4- (2-thioxanthenyl ketothio) phenyl ] phenyl-2-thioxanthenyl ketosulfonium phenyl tris (pentafluorophenyl) borate and 4- (phenylthio) phenyl diphenyl sulfonium hexafluoroantimonate; the free radical initiator may comprise: 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-phenyl-1-propanone, 2-hydroxy-1- [4- (2-hydroxyethoxy) phenyl ] -2-methyl-1-propanone, methyl benzoylformate, oxy-phenyl-acetic acid-2- [ 2-oxo-2-phenyl-acetoxy-ethoxy ] -ethyl ester, oxy-phenyl-acetic acid-2- [ 2-hydroxy-ethoxy ] -ethyl ester, alpha-dimethoxy-alpha-phenylacetophenone, 2-benzyl-2- (dimethylamino) -1- [4- (4-morpholinyl) phenyl ] -1-butanone, methyl ethyl hexanoate, methyl hexanoate, ethyl hexanoate, and its preparation method, 2-methyl-1- [4- (methylthio) phenyl ] -2- (4-morpholinyl) -1-acetone, diphenyl (2,4, 6-trimethylbenzoyl) phosphine oxide and diphenyl (2,4, 6-trimethylbenzoyl) phosphine oxide.
Preferably, the UV curable adhesive for polarizing plates, which is composed of an epoxy compound, (meth) acrylate compound, vinyl ether compound, carboxylic acid compound containing unsaturated double bond, cationic photoinitiator, and radical photoinitiator, is 100 parts by weight:
30 to 60 parts by weight of an alicyclic epoxy compound and 10 to 30 parts by weight of an aromatic epoxy compound, wherein the adhesive exhibits cracking resistance during thermal shock and adhesive strength for a triacetyl cellulose (TAC) film, a polyethylene terephthalate (PET) film and a cycloolefin polymer (COP) film;
the bifunctional (meth) acrylate compound accounts for 10 to 50 parts by weight, can improve the curing rate of the adhesive, can ensure intermediate adhesion between the polarizing plate and the optical film, and can avoid embrittlement by avoiding an excessive increase in the glass transition temperature when the epoxy resin compound is used;
1-20 parts by weight of a vinyl ether compound; 1-20 parts by weight of a carboxylic acid compound containing an unsaturated double bond; the cationic photoinitiator accounts for 0.01-10 parts by weight; the free radical initiator accounts for 0.01-10 parts by weight.
Preferably, the UV curing adhesive for the polarizing plate comprises 40-50 parts by weight of an epoxy compound, 10-20 parts by weight of a (meth) acrylate compound, 10-20 parts by weight of a vinyl ether compound, 10-20 parts by weight of a carboxylic acid compound containing an unsaturated double bond, 1-5 parts by weight of a cationic photoinitiator, and 1-5 parts by weight of a radical photoinitiator. The method for preparing the UV curing adhesive for the polarizing plate by using the mixed raw materials is a conventional technology, and can adopt the existing stirring and mixing.
The adhesive can fully cure epoxy compounds and (methyl) acrylate compounds, does not reduce the bonding strength, can prevent the transparency of an adhesive layer from being reduced, and also reduces the overflow of an initiator; the compound formed by hybrid curing of the adhesive contains carboxyl, can be firstly combined with moisture in a high-humidity environment, and solves the problem that in the prior art, in the high-humidity environment, hydroxyl groups on the surface of a polyvinyl alcohol (PVA) film are preferentially combined with moisture hydrogen bonds rather than hydrogen bonds of the free radical curable adhesive composition, so that the adhesiveness of the free radical curable adhesive composition is reduced. Accordingly, the present invention can prevent deterioration of adhesion of the radical curable adhesive composition by maintaining hydrogen bonds between the polyvinyl alcohol (PVA) -based film and the hydroxyl groups of the radical curable adhesive composition, thereby improving moisture resistance of the adhesive.
Drawings
FIG. 1 shows the effect of the adhesive application of example 8;
FIG. 2 shows the results of the wet heat resistance of the adhesive polarizing plate of example 8;
FIG. 3 shows the results of the wet heat resistance of the adhesive polarizing plate of comparative example 1.
Detailed Description
The UV curing adhesive for the polarizing plate designed in the invention applies the characteristics of the advantages of a delayed curing technology, an interpenetrating network (IPN) technology and a free radical-cation UV curing technology, and a vinyl ether compound and a carboxylic acid compound containing unsaturated double bonds are creatively added on the basis, so that the curing speed, the humidity resistance and the bonding strength of the adhesive are obviously improved while the higher bonding performance of the curing adhesive is ensured; the UV curing adhesive disclosed by the embodiment of the invention has better aging resistance and reliability. The examples are intended only to describe the invention in more detail and should not be construed as limiting the invention in any way.
The details of the components used in the examples and comparative examples are as follows:
a: bifunctional alicyclic epoxy compound: 3, 4-Epoxycyclohexylmethylcarboxylic acid 3, 4-epoxycyclohexylmethyl ester (TTA-21P, Jiangsu Taiter New Material science and technology Co., Ltd.)
Polyglycidyl ethers of aromatic compounds: resorcinol diglycidyl ether (XY-694, New science and technology Co., Ltd., Anhui)
Bifunctional (meth) acrylic acid compound: tripropylene glycol diacrylate (EM-223, Changxing materials industries, Ltd.)
Vinyl ether compound: diethylene glycol divinyl ether (EM-2241H, Guangzhou banyan chemical technology Co., Ltd.)
And E, carboxylic acid compounds containing unsaturated double bonds: maleic acid (Guangzhou Denli chemical industry Co., Ltd.)
F, cationic photoinitiator: diphenyl-4- (phenylthio) phenylsulfamoyl hexafluorophosphate (CPI-100P, San-Apro)
G is a radical initiator: diphenyl (2,4, 6-trimethylbenzoyl) phosphine oxide (JRCure-1108, New Material Ltd. Tianjin Jiu)
Examples
According to the parts by weight of table 1, a bifunctional alicyclic epoxy compound, a polyglycidyl ether of an aromatic compound, a bifunctional (meth) acrylic compound, a vinyl ether compound, a carboxylic acid compound containing an unsaturated double bond, a cationic photoinitiator, and a radical initiator were conventionally mixed to prepare a UV-curable adhesive for a polarizing plate. Wherein, in the embodiment 5, the vinyl ether compound is 4-hydroxybutyl vinyl ether; in example 6, the carboxylic acid compound having an unsaturated double bond is fumaric acid; in example 10, the carboxylic acid compound containing an unsaturated double bond was replaced with a conventional adhesion promoter, polycaprolactone triol; the remaining starting materials are as above for A to G.
Comparative example
A UV curable adhesive for a polarizing plate was prepared in the same manner as in example, except that the kinds or amounts of the respective components were changed, and the ratios of the respective components were maintained in accordance with example 8, as shown in table 1.
TABLE 1 example, comparative example Components (Unit: parts by weight)
Figure BDA0002669430840000071
Figure BDA0002669430840000081
The adhesives in examples and comparative examples were evaluated according to the characteristics listed in table 2, and the evaluation results are recorded in table 2.
Coating a UV curing adhesive on one surface of the optical film, and then covering the polarizer; and then ultraviolet light is cured to obtain the polarizing plate.
(1) Manufacture of polarizing plate
A polarizer of 23um thickness was manufactured by dyeing a 60um thick polyvinyl alcohol film (degree of saponification: 99.5, degree of polymerization: 2000) in a 0.3 wt% iodine aqueous solution, stretching the dyed film to 5.7 times the original length, and immersing the stretched film in a 3 wt% boric acid solution and a 2 wt% potassium iodide aqueous solution for color correction, followed by drying at 50 ℃ for 4 min; dyeing, stretching, color correction are conventional techniques.
As the optical film, an existing PET film, a TAC film and a COP film were used, wherein the PET film had a thickness of 80 μm (primer treatment, TA044, water vapor permeability: 10 g/m.day, Toyo Boseki Co., Ltd.); the TAC film was a 40um thick film with zero retardation (KC4CT1, water vapor permeability: 800 grams per square meter day, Cornica Ltd.); COP film thickness 52um (ZEONE, water vapor permeability: 5 g/m. day, Ramon Ltd.); the optical film is subjected to primer treatment or corona treatment, which is the prior art.
Coating the adhesive of the embodiment or the comparative example on one surface of the existing optical film by a conventional method to reach the thickness of 3um, and then covering a polarizer; followed by a subsequent treatment at UVA (800 mJ/cm)2) The polarizing plate was produced by photocuring under the conditions and used for the following tests.
FIG. 1 shows the effect of the adhesive application of example 8, without defects and without bubbles.
(2) Moisture and heat resistance
Cutting the obtained polarizing plate into 50 × 50mm sample plates, and soaking the sample plates in constant temperature water of 60 deg.C for 8 hr; the water resistance was evaluated according to the degree of bleaching at one end edge of the polarizing plate, and the evaluation results are shown in table 2 below.
No bleaching was evaluated as-.
FIG. 2 shows the results of the wet heat resistance of the adhesive polarizing plate of example 8, without any white edge; FIG. 3 shows the results of the wet heat resistance of the adhesive polarizing plate of comparative example 1, and the white edge is evident.
(3) Adhesion Property
The obtained polarizing plate was cut into a sample plate of 100 × 25mm size, and the polarizer and the optical film were separated by inserting a peeling machine into a gap between the polarizer and the optical film at one end of the sample plate, and then fixed to a jig on both sides of UTM (TA XT Plus, british SMS corporation) at both ends of each of the polarizer and the optical film, and the peeling force between the polarizer and the optical film was measured by a 90 ° peeling method. During the measurement, the polarizer and the other end of the optical film were pulled at a rate of 300mm/min in the opposite direction. The measurement results are shown in table 2 below.
The peel force > 4.0N/cm is very good, the peel force (inclusive) is 3.0N/cm to 4.0N/cm is good, the peel force (inclusive) is 2.0N/cm to 3.0N/cm is medium, the peel force is 1.0N/cm to 2.0N/cm is poor, and the peel force < 1.0N/cm is very poor.
The peel force of example 8 reached 5.6N/cm (PET film), 5.3N/cm (TAC film), 5.5N/cm (COP film); the conventional commercially available adhesive polarizing plate has a very small margin of about 0.1mm after resistance to heat and humidity, but has a low peeling force and selectivity of 3.1N/cm (PET film), 3.3N/cm (TAC film), and 1.9N/cm (COP film).
TABLE 2 test results of examples and comparative examples
Figure BDA0002669430840000091
Figure BDA0002669430840000101

Claims (7)

1. The UV curing adhesive-based polarizing plate comprises a polarizer, an optical film and a UV curing adhesive positioned between the polarizer and the optical film, and is characterized in that the UV curing adhesive consists of 40-50 parts by weight of epoxy compound, 10-20 parts by weight of (methyl) acrylate compound, 10-20 parts by weight of vinyl ether compound, 10-20 parts by weight of carboxylic acid compound containing unsaturated double bonds, 1-5 parts by weight of cationic photoinitiator and 1-5 parts by weight of free radical photoinitiator; the epoxy compound is 3, 4-epoxy cyclohexyl methyl formate-3, 4-epoxy cyclohexyl methyl ester and resorcinol diglycidyl ether; the (meth) acrylate compound is a bifunctional (meth) acrylate compound; the cationic photoinitiator is any one or combination of a plurality of diaryl iodonium salt, triaryl sulfonium salt and arylferrocenium salt compounds; the vinyl ether compound comprises at least one of diethylene glycol divinyl ether, 4-hydroxybutyl vinyl ether, 1, 4-butanediol vinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, tert-butyl vinyl ether, (vinyloxy) -2, 2-di ((vinyloxy) methyl) butane, 1, 3-di (vinyloxy) -2, 2-di ((vinyloxy) methyl) propane and cyclohexyl vinyl ether; the carboxylic acid compound containing unsaturated double bonds comprises at least one of maleic acid, fumaric acid, 2-methyl-2-butenoic acid and trans-2-methyl-2-butenoic acid.
2. The UV-curable adhesive-based polarizing plate according to claim 1, wherein the UV-curable adhesive for polarizing plates is obtained by mixing an epoxy compound, a (meth) acrylate compound, a vinyl ether compound, a carboxylic acid compound having an unsaturated double bond, a cationic photoinitiator, and a radical photoinitiator.
3. The UV-curable adhesive-based polarizing plate according to claim 1, wherein the bifunctional (meth) acrylate compound is a mono (alkylene glycol) bifunctional (meth) acrylate compound or a poly (alkylene glycol) bifunctional (meth) acrylate compound.
4. The UV-curable adhesive-based polarizing plate according to claim 1, wherein the radical initiator comprises: 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-phenyl-1-propanone, 2-hydroxy-1- [4- (2-hydroxyethoxy) phenyl ] -2-methyl-1-propanone, methyl benzoylformate, oxy-phenyl-acetic acid-2- [ 2-oxo-2-phenyl-acetoxy-ethoxy ] -ethyl ester, oxy-phenyl-acetic acid-2- [ 2-hydroxy-ethoxy ] -ethyl ester, alpha-dimethoxy-alpha-phenylacetophenone, 2-benzyl-2- (dimethylamino) -1- [4- (4-morpholinyl) phenyl ] -1-butanone, methyl ethyl hexanoate, methyl hexanoate, ethyl hexanoate, and its preparation method, 2-methyl-1- [4- (methylthio) phenyl ] -2- (4-morpholinyl) -1-acetone, diphenyl (2,4, 6-trimethylbenzoyl) phosphine oxide and phenyl bis (2,4, 6-trimethylbenzoyl) phosphine oxide.
5. The UV-curable adhesive-based polarizing plate according to claim 1, wherein the optical film is a PET film, a TAC film, or a COP film; the polaroid is a polyvinyl alcohol polaroid.
6. The method for producing a UV-curable adhesive-based polarizing plate according to claim 1, comprising the steps of mixing an epoxy compound, a (meth) acrylate compound, a vinyl ether compound, a carboxylic acid compound having an unsaturated double bond, a cationic photoinitiator, and a radical photoinitiator to obtain a UV-curable adhesive; and compounding the polaroid, the optical film and the UV curing adhesive to obtain the polarizing plate.
7. The method of manufacturing a UV-curable adhesive-based polarizing plate according to claim 6, wherein the UV-curable adhesive is applied to one surface of the optical film and then covered with the polarizer; and then ultraviolet light is cured to obtain the polarizing plate.
CN202010928766.1A 2020-09-07 2020-09-07 UV curing adhesive-based polarizing plate and preparation method thereof Active CN112011276B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202010928766.1A CN112011276B (en) 2020-09-07 2020-09-07 UV curing adhesive-based polarizing plate and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202010928766.1A CN112011276B (en) 2020-09-07 2020-09-07 UV curing adhesive-based polarizing plate and preparation method thereof

Publications (2)

Publication Number Publication Date
CN112011276A CN112011276A (en) 2020-12-01
CN112011276B true CN112011276B (en) 2022-06-17

Family

ID=73516055

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202010928766.1A Active CN112011276B (en) 2020-09-07 2020-09-07 UV curing adhesive-based polarizing plate and preparation method thereof

Country Status (1)

Country Link
CN (1) CN112011276B (en)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104395788B (en) * 2013-06-18 2017-07-28 Lg化学株式会社 Polarizer and the image display device including the Polarizer
KR101620164B1 (en) * 2013-09-30 2016-05-12 주식회사 엘지화학 Radical Curable Adhesive Composition And Polarizing Plate Comprising The Same
KR102084112B1 (en) * 2016-12-13 2020-03-03 삼성에스디아이 주식회사 Adhesive composition for polarizing plate, polarizing plate and optical display apparatus
KR20190059138A (en) * 2017-11-22 2019-05-30 삼성에스디아이 주식회사 Adhesive composition for polarizing plate, polarizing plate and optical display apparatus

Also Published As

Publication number Publication date
CN112011276A (en) 2020-12-01

Similar Documents

Publication Publication Date Title
TWI705893B (en) Polarizing film and manufacturing method thereof
TWI566938B (en) Polarizing plate, preparing method for polarizing plate and image display apparatus comprising the same
US20140162044A1 (en) Adhesive film for polarizing plate, adhesive composition for the same, polarizing plate comprising the same, and optical display apparatus comprising the same
KR102434552B1 (en) Polarizing film and method for producing same
TW201013240A (en) Polarizing plate and its production method, and liquid crystal display
JP6224848B2 (en) Radical curable adhesive composition, polarizing plate and optical member containing the same
TW201245382A (en) Photocurable adhesive, polarizing plate and laminated optical member
TW201142380A (en) Manufacturing method of polarizing plate
WO2013146556A1 (en) Polarizing plate
TWI641672B (en) Adhesive composition for polarizing plates, polarizing plate and optical display
TWI527695B (en) Polarizing plate and image display apparatus comprising the same
TWI731116B (en) Polarizing film with adhesion layer and manufacturing method of polarizing film with adhesion layer
CN112029420B (en) UV curing adhesive for polarizing plate and preparation method and application thereof
CN112011276B (en) UV curing adhesive-based polarizing plate and preparation method thereof
TW201412921A (en) Adhesive composition for polarizing plate, polarizing plate using the same and optical member
TW202018345A (en) Polarizing plate for light emitting displays and light emitting display comprising the same
TW201838819A (en) Optical laminate
CN109810637A (en) For the adhesive composition of polarization plates, polarization plates and optical display
KR102457858B1 (en) Bonding agent, bonded body, and method for manufacturing bonded body
JP6224833B2 (en) Radical curable adhesive composition and polarizing plate containing the same
KR101627928B1 (en) Radical curable adhesive composition, polarizing plate and optical member comprising the same
CN115315643A (en) Polarizer for light emitting display and light emitting display including the same
TW202134061A (en) Laminate
KR20190082624A (en) Adhesive composition for polarizing plate, polarizing plate and optical display apparatus
TW201527465A (en) Radical curable adhesive composition and polarizing plate comprising the same

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant