WO2020221178A1 - 光固化粘接剂组合物、光固化粘接剂、偏光板及光学设备 - Google Patents
光固化粘接剂组合物、光固化粘接剂、偏光板及光学设备 Download PDFInfo
- Publication number
- WO2020221178A1 WO2020221178A1 PCT/CN2020/087073 CN2020087073W WO2020221178A1 WO 2020221178 A1 WO2020221178 A1 WO 2020221178A1 CN 2020087073 W CN2020087073 W CN 2020087073W WO 2020221178 A1 WO2020221178 A1 WO 2020221178A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acrylate
- methacrylate
- component
- monomer
- light
- Prior art date
Links
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
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- 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
- C09J133/00—Adhesives based on 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/062—Copolymers with monomers not covered by C09J133/06
- C09J133/068—Copolymers with monomers not covered by C09J133/06 containing glycidyl groups
-
- 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
- C09J133/00—Adhesives based on 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/10—Homopolymers or copolymers of methacrylic acid esters
- C09J133/12—Homopolymers or copolymers of methyl methacrylate
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
Definitions
- the invention relates to the field of optical materials, and in particular to a light-curing adhesive composition, a light-curing adhesive, a polarizing plate and optical equipment.
- liquid crystal displays have been widely used in various display devices due to their low power consumption, low voltage operation, lightweightness and small size.
- the liquid crystal display may include many elements, such as liquid crystal cells, polarizing plates, retardation films, prism sheets, diffuser films, light guide plates, light reflection sheets, and the like. For this reason, improvements are being actively made by reducing the number of films used or making films or sheets thinner to increase productivity and improve brightness, and to make liquid crystal displays more portable.
- the polarizing plate includes a polarizing plate made of polyvinyl alcohol (PVA) resin dyed with dichroic dye or iodine, and a protective film stacked on one or both surfaces of the polarizing plate, wherein the polarizing plate and the protective film Set the adhesive between.
- PVA polyvinyl alcohol
- TAC Triacetyl cellulose
- protective films made of various materials that can replace TAC films were developed, and polyethylene terephthalate (PET) films, cycloolefin polymer (COP) films, acrylic films, or The concept of the combination of these films is constantly being proposed.
- Acrylic adhesive dry laminated adhesive made by mixing polyurethane resin solution and polyisocyanate resin solution, styrene/butadiene/rubber adhesive, epoxy adhesive, polyvinyl alcohol adhesive , Polyurethane adhesives, adhesives containing compounds with polyester ionomer polyurethane resins and glycidyl groups, thermosetting adhesives and other adhesives are constantly being developed, but these adhesives adhere to different films
- the force problem is a factor that needs to be considered, and the viscosity of the composition, the thickness that can be made, acid resistance, alkali resistance, and heat resistance are also factors that need to be considered.
- oxetane-based monomers have been developed. These oxetane-based compounds generally have the characteristics of low viscosity, low toxicity, fast polymerization speed, excellent thermal stability and mechanical properties, etc., which are used in cationic curing. The system can accelerate the polymerization speed and improve the performance of the cured product.
- the practical application of such monomers still has obvious shortcomings. The outstanding performance is that the types of compounds on the market are limited, and the comprehensive properties such as curing speed and hardness are difficult to balance, especially in polarized light. In the application of the board, the problem of the overall adhesion of the system after the introduction of oxetane compounds needs to be further optimized.
- the main purpose of the present invention is to provide a light-curing adhesive composition, light-curing adhesive, polarizing plate and optical equipment to solve the problem of insufficient adhesion of the light-curing adhesive in the prior art.
- a light-curable adhesive composition comprising: component A, which is an oxetane compound containing the following structure Wherein R represents phenyl, biphenyl, naphthyl, 0 ⁇ n ⁇ 4; component B: a compound with epoxy group; component C: a photoinitiator for cationic polymerization.
- component B includes: component B1: a polyglycidyl ether of a polyhydric alcohol having 2 to 10 carbon atoms; and component B2: a polymer having an epoxy group.
- the above component B1 is selected from ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, 1, 6-Hexanediol diglycidyl ether, dimethylolcyclohexane diglycidyl ether, 1,9-nonanediol diglycidyl ether, diethylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether Glycidyl ether, hydroquinone diglycidyl ether, resorcinol diglycidyl ether, trimethylolpropane triglycidyl ether, pentaerythritol tri- or tetra-glycidyl ether, and isocyanuric epoxy Any one or more of the group consisting of di- or triglycidyl ether,
- the Tg of the above component B2 is greater than or equal to 20°C, and the Mw is 1,000 to 30,000, preferably 3,000 to 20,000, and more preferably 5,000 to 15,000, where Mw refers to polystyrene conversion of the molecular weight measured by GPC And the weight average molecular weight obtained.
- the above component B2 is formed by polymerizing monomer b1, monomer b2 and optional monomer b3, wherein monomer b1 is a compound having epoxy groups and ethylenically unsaturated groups, and the ethylenic unsaturated groups are Vinyl or acryl, preferably monomer b1 is glycidyl acrylate, glycidyl methacrylate, 3,4-epoxycyclohexyl acrylate or 3,4-epoxycyclohexyl methacrylate; monomer b2 It is a monofunctional methacrylate having 1 to 10 carbon atoms, preferably monomer b2 is selected from methyl methacrylate, ethyl methacrylate, propyl methacrylate, isopropyl methacrylate, methacrylic acid Butyl ester, sec-butyl methacrylate, tert-butyl methacrylate, isobutyl methacrylate, hexyl me
- the above-mentioned component B2 includes 10-60% of monomer b1, 10-70% of monomer b2 and 0-60% of monomer b3.
- component C is selected from one or more combinations of iodonium salts, sulfonium salts, and aryl ferrocene salts.
- the weight content of component A is 25-55%, preferably 25-45%; the weight content of component B1 is 10-45%, and the weight content of component B2 The weight content is 20 to 80%, and the weight content of component C is 3 to 5%.
- a light-curing adhesive which is formed by polymerization of a light-curing adhesive composition, the light-curing adhesive composition being any of the above-mentioned light-curing adhesive combinations Things.
- a polarizing plate which includes a polarizer and a protective film bonded to the polarizer by an adhesive, the adhesive being the above-mentioned light-curing adhesive.
- an optical device including a polarizing plate, the polarizing plate being the aforementioned polarizing plate.
- the prior art oxetane compounds have the characteristics of low viscosity, low toxicity, good polymerization speed, excellent thermal stability and mechanical properties, but still have curability in practical applications.
- the curing speed and hardness are difficult to balance, especially in the application of polarizers.
- the overall adhesion effect of the adhesive after the introduction of oxetane compounds is not ideal.
- this application provides A light-curing adhesive composition, light-curing adhesive, polarizing plate and optical equipment.
- a light-curable adhesive composition including component A, component B and component C, wherein component A is an oxetane having the following structure Compound Wherein R represents phenyl, biphenyl, naphthyl, 0 ⁇ n ⁇ 4; component B is a compound with epoxy group; component C is a photoinitiator for cationic polymerization.
- a specific oxetane compound is used in conjunction with a compound having an epoxy group and a cationic polymerization photoinitiator to make the formed photocurable adhesive have adhesion, curability, and protection of the polarizer.
- the adhesion of the film is improved.
- the aforementioned component B includes component B1 and component B2.
- Component B1 is a polyglycidyl ether of a polyhydric alcohol with 2 to 10 carbon atoms; component B2 is an epoxy group Of polymers.
- the combination of the above two epoxy-containing compounds and the oxetane compound can further improve the adhesiveness of the photocurable adhesive.
- the aforementioned component B1 is selected from ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6 -Hexanediol diglycidyl ether, dimethylolcyclohexane diglycidyl ether, 1,9-nonanediol diglycidyl ether, diethylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether Glyceryl ether, hydroquinone diglycidyl ether, resorcinol diglycidyl ether, trimethylolpropane triglycidyl ether, pentaerythritol tri- or tetraglycidyl ether, and isocyanuric acid ethylene oxide Any one or more of the group consisting of di- or trig
- the Tg of the above component B2 is greater than or equal to 20°C (the same as the conventional measurement method in the prior art, that is, using a differential scanning calorimeter (DSC) , The value measured at a temperature increase rate of 10°C/min), Mw is 1,000 to 30,000, preferably 3,000 to 20,000, and more preferably 5,000 to 15,000, where Mw means the molecular weight measured by GPC is converted into polystyrene Weight average molecular weight obtained by conversion.
- Mw means the molecular weight measured by GPC is converted into polystyrene Weight average molecular weight obtained by conversion.
- the aforementioned component B2 is formed by polymerization of monomer b1, monomer b2 and optional monomer b3.
- Component B2 is a polymer with low Mw.
- a chain transfer agent and/or a polymerization initiator When it is desired to produce such a polymer by a normal polymerization method, it is usually necessary to increase a chain transfer agent and/or a polymerization initiator.
- a polymer formed of a large amount of a chain transfer agent is used, the cationic curability and/or adhesive force of the composition tends to be lowered, and the storage stability of the composition also tends to be lowered.
- the monomer b1 is preferably a compound with epoxy groups and ethylenically unsaturated groups. It is vinyl or acryl, preferably monomer b1 is glycidyl acrylate, glycidyl methacrylate, 3,4-epoxycyclohexyl acrylate or 3,4-epoxycyclohexyl methacrylate; monomer b2 is a monofunctional methacrylate having 1 to 10 carbon atoms, preferably monomer b2 is selected from methyl methacrylate, ethyl methacrylate, propyl methacrylate, isopropyl methacrylate, methyl Butyl acrylate, sec-butyl methacrylate, tert-butyl methacrylate, isobutyl methacrylate, hexyl methacrylate, cyclohex
- the monomer b1 and the monomer b2 as essential structural monomer units are copolymerized with the component B1 and the component A which are the cation curable compound.
- the above-mentioned monomer b1 is particularly preferably glycidyl methacrylate
- the above-mentioned monomer b2 is particularly preferably methyl methacrylate, ethyl methacrylate, cyclohexyl methacrylate and benzyl methacrylate to adjust the reactivity , System viscosity, etc. can be further added monomer b3.
- component B2 includes 10-60% of monomer b1, 10-70% of monomer b2, and 0-60% of monomer b3.
- the component The weight content of styrene in B2 is 5 to 45%, preferably 10 to 40%; when monomer b3 contains monofunctional acrylate, the weight content of monofunctional acrylate in component B2 is 1 to 30%, preferably 5-25%; preferably component B2 includes 10-70% by weight methyl methacrylate as monomer b2, and 1-50% by weight styrene as monomer b3; preferably component B2 includes weight Glycidyl methacrylate with a content of 10-60% as monomer b1, methyl methacrylate with a weight content of 10 to 70% as monomer b2, and a weight content of 1-30% with carbon atoms of 1 to A monofunctional acrylate of a hydrocarbon group of 10 is used as the monomer b3.
- the aforementioned component C is selected from one or more combinations of iodonium salts, sulfonium salts, and aryl ferrocene salts, and preferably has the following formula (I) and/ Or the compound of the structure shown in (II):
- R 1 and R 2 each independently represent hydrogen, a C 1 -C 20 linear or branched alkyl group, a C 4 -C 20 cycloalkylalkyl group or an alkylcycloalkyl group, and among these groups
- the acyclic -CH 2 - can be optionally substituted by -O-, -S- or 1,4-phenylene
- R 3 and R 4 each independently represent hydrogen, C 1 -C 20 linear or Branched chain alkyl, C 4 -C 20 cycloalkyl alkyl or alkyl cycloalkyl, C 6 -C 20 substituted or unsubstituted aryl, and the non-cyclic -CH 2 -in these groups may Optionally substituted by -O-, -S- or 1,4-phenylene
- R 5 represents C 6 -C 20 substituted or unsubstituted aryl, C 6 -C 20 substituted or unsubstituted alkyl Aryl, C
- R 1 and R 2 each independently represent hydrogen, C 1 -C 12 linear or branched alkyl, C 4 -C 10 Cycloalkylalkyl or alkylcycloalkyl, and the acyclic -CH 2 -in these groups may be optionally substituted by -O-;
- R 3 and R 4 each independently represent hydrogen, C 1 -C 10 straight or branched chain alkyl groups, C 4 -C 10 cycloalkylalkyl groups or alkylcycloalkyl groups, C 6 -C 12 substituted or unsubstituted aryl groups, and these groups are non-cyclic- CH 2 -may be optionally substituted by -O-, -S- or 1,4-phenylene;
- R 5 represents C 6 -C 10 substituted or unsubstituted aryl, C 6 -C 10 substituted or Unsubstituted alkyl aryl, substituted or
- cationic photoinitiators with similar structures can also be used in component C of the present invention. Examples include (but not limited to): PAG20001, PAG20001s, PAG20002, PAG20002s, PAG30201, PAG30101, etc. produced by Tronly, etc. Irgacure250 produced by the company.
- the amount of each component can refer to the amount of the corresponding component in the prior art, preferably based on the light-curing adhesive composition, and the weight content of component A is 25- 60%, preferably 25 to 55%, more preferably 25 to 45%; the weight content of component B1 is 10 to 45%, preferably 10 to 35%, and the weight content of component B2 is 15 to 80%, preferably It is 20 to 80%, more preferably 15 to 35%, and the weight content of component C is 3 to 5%, preferably 5%.
- the photocurable adhesive in the application of the present invention can optionally be added with organic and/or inorganic additives commonly used in the field, including but not limited to leveling agents, dispersants, curing agents, surface Active agents, solvents, etc. are obvious to those skilled in the art.
- organic and/or inorganic additives commonly used in the field, including but not limited to leveling agents, dispersants, curing agents, surface Active agents, solvents, etc. are obvious to those skilled in the art.
- other sensitizers and/or photoinitiators can also be added to the adhesive for compound use.
- one or more macromolecules or polymer compounds can be selectively added to the photocurable adhesive to improve application performance.
- This macromolecule or polymer compound can be polyol or polyester polyol ; Can also optionally add polymers that do not contain reactive functional groups. These polymers are usually resins containing acidic functional groups such as phenolic hydroxyl groups and carboxyl groups.
- a light-curing adhesive is provided, which is formed by polymerization of a light-curing adhesive composition, and the light-curing adhesive composition is any one of the above-mentioned light-curing adhesives.
- Adhesive composition is any one of the above-mentioned light-curing adhesives.
- the photocurable adhesive composition of the present application selects a specific oxetane compound, a compound having an epoxy group, and a cationic polymerization photoinitiator for use, the adhesion of the formed photocurable adhesive is Curability and adhesion to polarizers and protective films are improved.
- a polarizing plate which includes a polarizer and a protective film bonded to the polarizer by an adhesive, and the adhesive is the above-mentioned photocurable adhesive. Since the photocurable adhesive of the present application has good adhesion, acid resistance, alkali resistance, and excellent thermal stability, the polarizing plate using it as the adhesive has a longer service life and better optical performance.
- the photocurable adhesive of the present application can be used to bond a protective film on a polarizer formed of a polyvinyl alcohol-based resin film, for example, for a film that is uniaxially stretched and a dichroic dye is oriented by adsorption
- a protective film is adhered to a polarizer formed of a polyvinyl alcohol-based resin film, and the protective film is bonded to the polarizer in this way to form a polarizer.
- the protective film may be attached to only one side of the polarizer, or may be attached to both sides of the polarizer. When the protective films are bonded to both sides of the polarizer, each protective film may be a protective film formed of the same type of resin, or may be a protective film formed of a different type of resin.
- the manufacturing method includes: laminating a protective film on one or both sides of the polarizer using a photocurable adhesive, and curing the photocurable adhesive by light radiation.
- More specific processes can include:
- Coating process apply the light-curable adhesive on the protective film in an uncured state to form an adhesive coating surface
- 2Laminating process laminating the polarizer on the adhesive coating surface of the protective film
- 3Curing process Use light radiation to cure the photocurable adhesive to form an adhesive layer.
- the protective film can be attached to one side or both sides.
- at least one of the protective films on both sides has other optical functions.
- polarizer a conventional type in the art can be used, for example, a polyvinyl alcohol-based resin film that has been uniaxially stretched and has been adsorbed or oriented with iodine or a dichroic dye.
- an optical device including a polarizing plate, and the polarizing plate is the aforementioned polarizing plate.
- a polarizing plate When a polarizing plate is used, it can also be an optical member obtained by laminating an optical layer showing an optical function other than the polarizing function on one side.
- the optical member one or two or more layers selected from the aforementioned reflective layer or semi-transmissive reflective layer, light scattering layer, retardation plate, condensing plate, brightness enhancement film, etc., can be selected according to the purpose of use.
- the optical layers are combined to form a two-layer or three-layer laminate.
- the various optical layers forming the optical member are integrated with the polarizing plate by using an adhesive.
- the photocurable adhesives prepared in the examples and comparative examples were subjected to defoaming treatment, and they were applied to an 80 ⁇ m-thick triacetyl cellulose (TAC) protective film (trade name Fujitech, Fujifilm Corporation) using a bar coater On top, the thickness of the coating film is 10 ⁇ m, and then the polyvinyl alcohol-iodine polarizer is bonded together. Next, the same adhesive was applied to the other side of the polarizing plate to a thickness of 10 ⁇ m, and a norbornene-based resin film (trade name ZEONOR, OPTES) was bonded to this surface. Then, a mercury lamp (exposure machine model RW-UV20101, accumulatively receiving 2000mJ/cm 2 radiation energy) was used for curing.
- TAC triacetyl cellulose
- the adhesion, curing performance and adhesion performance are evaluated.
- the specific evaluation methods and standards are as follows:
- Adhesion is tested with ARCOTEST dyne pens, and the lines are evenly distributed. The largest dyne pen without any bead points within 3 seconds is the dyne test. The smaller the surface dyne value, the greater the surface tension of the attached bottom layer. The more conducive to adhesion.
- the adhesiveness of the protective films (that is, TAC film and norbornene film) on both sides was evaluated respectively, and the classification was performed as follows:
- the protective film cannot be peeled off from the polarizer at the interface. Forcible peeling will cause damage to the film-indicating excellent adhesion;
- the protective film can be peeled off from the polarizer at the interface without damage to the film-indicating good adhesion
- a component (see Table 1 for details) 25 parts by mass
- Component B1 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanoate 35 parts by mass
- B2 component heated polymerization of glycidyl methacrylate/methyl methacrylate/hydroxyethyl acrylate (mass ratio 30:40:30, Mw is 12000) 35 parts by mass
- Component A 35 parts by mass
- B1 component 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanoate 25 parts by mass
- B2 component heated polymerization of glycidyl methacrylate/methyl methacrylate/hydroxyethyl acrylate (mass ratio 30:40:30, Mw is 12000) 35 parts by mass
- Component A (see Table 3 for details) 40 parts by mass
- B1 component pentaerythritol tetraglycidyl ether 30 parts by mass
- B2 component heat polymerization of glycidyl methacrylate/methyl methacrylate/hydroxyethyl acrylate (mass ratio 30:40:30, Mw is 12000) 25 parts by mass
- the adhesive composition of the present invention has good curing effect, good adhesion, and adhesion to TAC film and norbornene film.
- the reason for analysis may be that the oxetane compound in the composition formula of the present invention is a monofunctional oxygen heterocycle, with moderate viscosity, and the presence of benzyl in the group makes its curing speed faster, thus having excellent Comprehensive application performance.
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polarising Elements (AREA)
- Polyethers (AREA)
- Epoxy Resins (AREA)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2021564394A JP7386896B2 (ja) | 2019-04-29 | 2020-04-26 | 光硬化型接着剤組成物、光硬化型接着剤、偏光板及び光学設備 |
KR1020217038921A KR102624880B1 (ko) | 2019-04-29 | 2020-04-26 | 광경화성 접착제 조성물, 광경화성 접착제, 편광판 및 광학 디바이스 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910357369.0 | 2019-04-29 | ||
CN201910357369.0A CN111849394B (zh) | 2019-04-29 | 2019-04-29 | 光固化粘接剂组合物、光固化粘接剂、偏光板及光学设备 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2020221178A1 true WO2020221178A1 (zh) | 2020-11-05 |
Family
ID=72966567
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CN2020/087073 WO2020221178A1 (zh) | 2019-04-29 | 2020-04-26 | 光固化粘接剂组合物、光固化粘接剂、偏光板及光学设备 |
Country Status (4)
Country | Link |
---|---|
JP (1) | JP7386896B2 (ja) |
KR (1) | KR102624880B1 (ja) |
CN (1) | CN111849394B (ja) |
WO (1) | WO2020221178A1 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114507416A (zh) * | 2020-11-16 | 2022-05-17 | 常州强力先端电子材料有限公司 | 光固化组合物、涂料及其制备方法、碳纤维预浸料及其制备方法和纤维复合材料 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101776846A (zh) * | 2009-01-14 | 2010-07-14 | 北京光创物成材料科技有限公司 | 激光造型专用光固化组份 |
CN103497691A (zh) * | 2009-03-06 | 2014-01-08 | 住友化学株式会社 | 光固化性粘接剂组合物、偏振板及其制造法、光学部件以及液晶显示装置 |
JP2015040283A (ja) * | 2013-08-23 | 2015-03-02 | 東亞合成株式会社 | 光硬化性接着剤組成物、偏光板とその製造法、光学部材及び液晶表示装置 |
CN104745104A (zh) * | 2013-12-25 | 2015-07-01 | 东亚合成株式会社 | 光固化性粘接剂组合物、偏光板及其制造方法、光学构件以及液晶显示装置 |
CN104910843A (zh) * | 2014-03-12 | 2015-09-16 | 东莞新科技术研究开发有限公司 | 可阳离子固化的粘接剂及其应用 |
CN109400551A (zh) * | 2017-08-17 | 2019-03-01 | 常州强力先端电子材料有限公司 | 氧杂环丁烷化合物及其制备方法 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001040085A (ja) | 1999-08-04 | 2001-02-13 | Toagosei Co Ltd | カチオン硬化性組成物 |
JP2001207150A (ja) * | 2000-01-26 | 2001-07-31 | Sony Chem Corp | 接着剤組成物 |
JP4395577B2 (ja) | 2001-10-31 | 2010-01-13 | 東亞合成株式会社 | エネルギー線硬化性接着剤組成物 |
JP2005113123A (ja) | 2003-09-18 | 2005-04-28 | Fuji Photo Film Co Ltd | 光硬化型接着剤及びこれを用いる接着方法 |
WO2005045525A1 (en) * | 2003-11-06 | 2005-05-19 | Dsm Ip Assets B.V. | Curable compositions and rapid prototyping process using the same |
WO2006029095A1 (en) * | 2004-09-03 | 2006-03-16 | Henkel Corporation | Photoinitiated cationic epoxy compositions |
JP5037074B2 (ja) | 2006-09-06 | 2012-09-26 | 協立化学産業株式会社 | 光カチオン硬化型又は熱カチオン硬化型接着剤 |
JP2011236389A (ja) | 2010-05-13 | 2011-11-24 | Toyo Ink Sc Holdings Co Ltd | 偏光板形成用光硬化性接着剤及び偏光板 |
JP6085130B2 (ja) | 2012-09-07 | 2017-02-22 | 旭化成株式会社 | 液状樹脂組成物、及び加工品 |
JP6284721B2 (ja) | 2013-08-26 | 2018-02-28 | 株式会社Adeka | エネルギー線感受性組成物 |
JP2015078314A (ja) | 2013-10-17 | 2015-04-23 | セメダイン株式会社 | 光硬化性組成物 |
RU2744431C2 (ru) * | 2016-05-19 | 2021-03-09 | Сикпа Холдинг Са | Адгезивы для сборки компонентов инертного материала |
JP6880809B2 (ja) | 2016-12-09 | 2021-06-02 | 東亞合成株式会社 | 活性エネルギー線硬化型封止剤用組成物 |
-
2019
- 2019-04-29 CN CN201910357369.0A patent/CN111849394B/zh active Active
-
2020
- 2020-04-26 JP JP2021564394A patent/JP7386896B2/ja active Active
- 2020-04-26 WO PCT/CN2020/087073 patent/WO2020221178A1/zh active Application Filing
- 2020-04-26 KR KR1020217038921A patent/KR102624880B1/ko active IP Right Grant
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101776846A (zh) * | 2009-01-14 | 2010-07-14 | 北京光创物成材料科技有限公司 | 激光造型专用光固化组份 |
CN103497691A (zh) * | 2009-03-06 | 2014-01-08 | 住友化学株式会社 | 光固化性粘接剂组合物、偏振板及其制造法、光学部件以及液晶显示装置 |
JP2015040283A (ja) * | 2013-08-23 | 2015-03-02 | 東亞合成株式会社 | 光硬化性接着剤組成物、偏光板とその製造法、光学部材及び液晶表示装置 |
CN104745104A (zh) * | 2013-12-25 | 2015-07-01 | 东亚合成株式会社 | 光固化性粘接剂组合物、偏光板及其制造方法、光学构件以及液晶显示装置 |
CN104910843A (zh) * | 2014-03-12 | 2015-09-16 | 东莞新科技术研究开发有限公司 | 可阳离子固化的粘接剂及其应用 |
CN109400551A (zh) * | 2017-08-17 | 2019-03-01 | 常州强力先端电子材料有限公司 | 氧杂环丁烷化合物及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
KR20220002562A (ko) | 2022-01-06 |
KR102624880B1 (ko) | 2024-01-12 |
JP7386896B2 (ja) | 2023-11-27 |
CN111849394B (zh) | 2021-12-28 |
JP2022531208A (ja) | 2022-07-06 |
CN111849394A (zh) | 2020-10-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TWI596179B (zh) | 壓敏性黏著劑組成物 | |
TWI607074B (zh) | Photocurable adhesive composition, polarizing plate and manufacturing method therefor, optical member and liquid crystal display device | |
KR101496506B1 (ko) | 편광판용 접착제 및 이를 포함하는 편광판 | |
TWI669571B (zh) | 光硬化性接著劑組成物、偏光板及其製造法、光學構件及液晶顯示裝置 | |
TWI512074B (zh) | 光硬化性接著劑組成物、偏光板及其製作方法、光學構件及液晶顯示裝置 | |
TWI629329B (zh) | 光硬化性接著劑組成物、偏光板及其製造方法、光學構件、以及液晶顯示裝置 | |
US10132976B2 (en) | Polarizing plate, method for manufacturing same, and image display device comprising same | |
JP6066707B2 (ja) | 偏光フィルムの製造方法 | |
KR101114924B1 (ko) | 프라이머 코팅 조성물, 이를 포함하는 광학 필름 및 이를 포함하는 편광판 | |
JP5267919B2 (ja) | 偏光板、光学部材および液晶表示装置 | |
JP2017122936A (ja) | 偏光板保護フィルム、偏光板、液晶表示装置および偏光板保護フィルムの製造方法 | |
JP2013160775A (ja) | 偏光板及び光学部材 | |
JP6119109B2 (ja) | 偏光板及び液晶表示装置 | |
JP2011219548A (ja) | 光硬化性接着剤組成物、偏光板とその製造法、光学部材及び液晶表示装置 | |
TWI510585B (zh) | 丙烯酸黏合劑組合物、偏振板和包含該偏振板之液晶顯示器 | |
KR20160049449A (ko) | 편광판 및 이를 포함하는 화상표시장치 | |
CN114761839A (zh) | 固化性粘接剂组合物及偏振板 | |
WO2020221178A1 (zh) | 光固化粘接剂组合物、光固化粘接剂、偏光板及光学设备 | |
TW201910827A (zh) | 偏光板用黏著劑組成物及附設黏著劑層之偏光板 | |
TWI646349B (zh) | 偏光板之製造方法 | |
JP2016206684A (ja) | 偏光板及び光学部材 | |
KR101526032B1 (ko) | 광학 소자용 조성물 | |
KR101687872B1 (ko) | 라디칼 경화형 접착제 조성물 및 이를 포함하는 편광판 | |
KR20130034907A (ko) | 광학 소자용 조성물 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 20799084 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2021564394 Country of ref document: JP Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
ENP | Entry into the national phase |
Ref document number: 20217038921 Country of ref document: KR Kind code of ref document: A |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 20799084 Country of ref document: EP Kind code of ref document: A1 |