CN113801623A - Adhesive for electronic component and adhesive for display element - Google Patents

Adhesive for electronic component and adhesive for display element Download PDF

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Publication number
CN113801623A
CN113801623A CN202111283440.9A CN202111283440A CN113801623A CN 113801623 A CN113801623 A CN 113801623A CN 202111283440 A CN202111283440 A CN 202111283440A CN 113801623 A CN113801623 A CN 113801623A
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moisture
meth
light
acrylate
adhesive
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高桥彻
国广良隆
结城彰
木田拓身
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Sekisui Chemical Co Ltd
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Sekisui Chemical Co Ltd
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    • C—CHEMISTRY; METALLURGY
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    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C08L75/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • C—CHEMISTRY; METALLURGY
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
    • C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/302—Water
    • C08G18/307—Atmospheric humidity
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4825—Polyethers containing two hydroxy groups
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7678—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing condensed aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
    • 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
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • 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
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
    • 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
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors

Abstract

The purpose of the present invention is to provide a light/moisture-curable resin composition having excellent light-shielding properties and adhesion properties. Further, the present invention aims to provide an adhesive for electronic components and an adhesive for display elements, which are produced using the light/moisture curable resin composition. The light and moisture curable resin composition of the present invention contains a radical polymerizable compound, a moisture curable urethane resin, a photo radical polymerization initiator, and a light-shading agent.

Description

Adhesive for electronic component and adhesive for display element
This application is a divisional application of an invention patent application having an application date of 2015, 20/01, application number of 201580001617.8 and having an invention name of "light-moisture-curable resin composition, adhesive for electronic parts, and adhesive for display elements".
Technical Field
The present invention relates to a light/moisture curable resin composition having excellent light-shielding properties and adhesion properties. The present invention also relates to an adhesive for electronic components and an adhesive for display elements, which are produced using the light/moisture-curable resin composition.
Background
In recent years, liquid crystal display elements, organic EL display elements, and the like have been widely used as display elements having features such as thinness, lightweight, and low power consumption. In these display elements, a photocurable resin composition is generally used for sealing a liquid crystal and a light-emitting layer, and for bonding a substrate, an optical film, a protective film, various members, and the like.
In addition, in the modern day in which various mobile devices with display elements such as mobile phones and mobile game machines are increasingly widespread, miniaturization of the display elements is the most demanded issue, and as a method for miniaturization, narrowing of the image display portion (hereinafter, also referred to as narrow-edge design) has been performed. However, in the narrow-edged design, a portion which is not sufficiently reached by light may be coated with the photocurable resin composition, and as a result, there is a problem that the photocurable resin composition applied to the portion which is not reached by light is insufficiently cured.
Further, even when the photocurable resin composition is disposed in a portion which is not sufficiently reached by light, there are problems as follows: light transmitted through the photocurable resin composition from the light emitting part of the display element cannot be shielded, and the contrast is lowered due to light leakage.
Therefore, a method of adding a light-shielding agent to the photocurable resin composition is conceivable. However, the photocurable resin composition containing a light-shading agent has a problem of insufficient photocuring. Patent document 1 discloses a method of blending a light-shading agent to a photo-thermal curable resin composition which can be sufficiently cured by heating even when photocuring is insufficient, but heating at a high temperature may adversely affect elements and the like.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2006-099027
Disclosure of Invention
Problems to be solved by the invention
The purpose of the present invention is to provide a light/moisture-curable resin composition having excellent light-shielding properties and adhesion properties. Further, the present invention aims to provide an adhesive for electronic components and an adhesive for display elements, which are produced using the light/moisture curable resin composition.
Means for solving the problems
The light and moisture curable resin composition of the present invention contains a radical polymerizable compound, a moisture curable urethane resin, a photo radical polymerization initiator, and a light-shading agent.
The present invention will be described in detail below.
The present inventors have found that a light-moisture-curable resin composition having both excellent light-shielding properties and excellent adhesiveness can be obtained by adding a light-shielding agent to a light-moisture-curable resin composition containing a radical-polymerizable compound, a moisture-curable urethane resin and a photo-radical polymerization initiator as a method for curing the light-moisture-curable resin composition without heating the light-shielding agent at a high temperature, and have completed the present invention.
The moisture-curable resin composition of the present invention contains a light-screening agent. By containing the light-shading agent, the moisture-curable resin composition of the present invention is excellent in light-shading properties and can prevent light leakage from a display element.
In the present specification, the "light-screening agent" refers to a material having an ability to transmit light in the visible light range with difficulty.
Examples of the light-shading agent include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, and resin-coated carbon black. The light-shading agent may not be black, and any material having an ability to transmit light in the visible light range with difficulty may be used, and materials exemplified as fillers described later, such as silica and talc, are also included in the light-shading agent. Among them, titanium black is preferable.
The titanium black has a higher transmittance for light in the vicinity of the ultraviolet region, particularly at a wavelength of 370 to 450nm, than the average transmittance for light having a wavelength of 300 to 800 nm. That is, the titanium black is a light-shielding agent which sufficiently shields light having a wavelength in the visible light region, thereby imparting light-shielding properties to the moisture-curable resin composition of the present invention, and which transmits light having a wavelength in the vicinity of the ultraviolet light region. Therefore, the photo-curing property of the moisture curable resin composition of the present invention can be further enhanced by using, as the photo-radical polymerization initiator, a substance capable of initiating a reaction by light having a wavelength (370 to 450nm) at which the transmittance of the titanium black becomes high. On the other hand, as the light-shading agent contained in the moisture-curable resin composition of the present invention, a material having high insulation properties is preferable, and as the light-shading agent having high insulation properties, titanium black is also preferable.
The optical density (OD value) of the titanium black is preferably 3 or more, and more preferably 4 or more. The degree of blackness (L value) of the titanium black is preferably 9 or more, and more preferably 11 or more. The higher the light-shielding property of the titanium black, the better, and the preferable upper limit of the OD value of the titanium black is not particularly limited, but is usually 5 or less.
The titanium black exhibits a sufficient effect even if it is not surface-treated, and surface-treated titanium black such as a material whose surface is treated with an organic component such as a coupling agent, or a material whose surface is covered with an inorganic component such as silicon oxide, titanium oxide, germanium oxide, aluminum oxide, zirconium oxide, or magnesium oxide may be used. Among them, titanium black treated with an organic component is preferable in that the insulating property can be further improved.
In addition, since the moisture-curable resin composition of the present invention has sufficient light-shielding properties, a liquid crystal display element manufactured using the moisture-curable resin composition of the present invention can realize high contrast without light leakage and excellent image display quality.
Examples of commercially available products of the titanium black include 12S, 13M-C, 13R-N (all manufactured by Mitsubishi synthetic materials Co., Ltd.), and Tilack D (manufactured by Gibberella chemical Co., Ltd.).
The lower limit of the specific surface area of the titanium black is preferably 5m2A preferred upper limit of 40 m/g2A more preferred lower limit is 10m2A more preferred upper limit is 25 m/g2/g。
The preferable lower limit of the sheet resistance (シート resistance) of the titanium black is 10 when mixed with a resin (70% blend)9Omega/□, more preferably the lower limit is 1011Ω/□。
In the moisture-curable resin composition of the present invention, the primary particle size of the light-shading agent is appropriately selected depending on the application, such as the distance between substrates of the display device or less, and the lower limit is preferably 30nm, and the upper limit is preferably 500 nm. When the primary particle size of the light-shading agent is less than 30nm, the viscosity and thixotropy of the obtained moisture-curable resin composition may be significantly increased, and the workability may be deteriorated. When the primary particle diameter of the light-shading agent is larger than 500nm, dispersibility of the light-shading agent in the obtained moisture-curable resin composition may be lowered, and light-shading properties may be lowered. The lower limit of the primary particle diameter of the light-shading agent is more preferably 50nm, and the upper limit is more preferably 200 nm.
The content of the light-shading agent in the entire moisture-curable resin composition of the present invention is not particularly limited, but is preferably 0.05% by weight at the lower limit and 10% by weight at the upper limit. If the content of the light-shielding agent is less than 0.05 wt%, sufficient light-shielding properties may not be obtained. When the content of the light-shading agent is more than 10% by weight, the adhesiveness of the obtained moisture-curable resin composition to a substrate or the like, the strength after curing, or the drawing property may be lowered. The lower limit of the content of the light-shading agent is more preferably 0.1% by weight, the upper limit is more preferably 2% by weight, the lower limit is more preferably 0.3% by weight, and the upper limit is more preferably 1% by weight.
The moisture-curable resin composition of the present invention contains a radical polymerizable compound.
The radical polymerizable compound is not particularly limited as long as it is a compound having a radical reactive functional group in a molecule, and a compound having an unsaturated double bond is preferable as the radical reactive functional group, and a resin having a (meth) acryloyl group (hereinafter, also referred to as a "(meth) acrylic resin") is preferable in particular from the viewpoint of reactivity.
In the present specification, the "(meth) acryloyl group" means an acryloyl group or a methacryloyl group, and the "(meth) acrylic group" means an acrylic group or a methacrylic group.
Examples of the (meth) acrylic resin include ester compounds obtained by reacting a compound having a hydroxyl group with (meth) acrylic acid; an epoxy-based (meth) acrylate obtained by reacting (meth) acrylic acid with an epoxy compound; urethane (meth) acrylate or the like is obtained by reacting an isocyanate with a (meth) acrylic acid derivative having a hydroxyl group.
In the present specification, the "(meth) acrylate" refers to an acrylate or a methacrylate.
Examples of the monofunctional compound in the above-mentioned ester compounds include phthalimide acrylates such as N-acryloyloxyethylhexahydrophthalimide, various imide acrylates, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, isooctyl (meth) acrylate, lauryl (meth) acrylate, octadecyl (meth) acrylate, isobornyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, methoxyethylene glycol (meth) acrylate, 2-ethoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, and mixtures thereof, Benzyl (meth) acrylate, ethyl carbitol (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, 2,2, 2-trifluoroethyl (meth) acrylate, 2,2,3, 3-tetrafluoropropyl (meth) acrylate, 1H, 5H-octafluoropentyl (meth) acrylate, imide (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, propyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isononyl (meth) acrylate, isomyristyl (meth) acrylate, 2-butoxyethyl (meth) acrylate, n-butyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, imide (meth) acrylate, methyl (meth) acrylate, ethyl (2, n-butyl (meth) acrylate, propyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, n-butyl acrylate, and (meth) acrylate, 2-phenoxyethyl (meth) acrylate, dicyclopentenyl (meth) acrylate, isodecyl (meth) acrylate, diethylaminoethyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, 2- (meth) acryloyloxyethylsuccinic acid, 2- (meth) acryloyloxyethylhexahydrophthalic acid, 2- (meth) acryloyloxyethyl-2-hydroxypropylphthalate, glycidyl (meth) acrylate, 2- (meth) acryloyloxyethyl phosphate, and the like.
Examples of the 2-functional compound in the ester compound include 1, 4-butanediol di (meth) acrylate, 1, 3-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, 1, 9-nonanediol di (meth) acrylate, 1, 10-decanediol di (meth) acrylate, 2-n-butyl-2-ethyl-1, 3-propanediol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene oxide-added bisphenol a di (meth) acrylate, ethylene oxide-added bisphenol a di (meth) acrylate, Ethylene oxide-added bisphenol F di (meth) acrylate, dimethylol biscyclopentadienyl di (meth) acrylate, neopentyl glycol di (meth) acrylate, ethylene oxide-modified isocyanuric acid di (meth) acrylate, 2-hydroxy-3- (meth) acryloyloxypropyl (meth) acrylate, carbonate diol di (meth) acrylate, polyether diol di (meth) acrylate, polyester diol di (meth) acrylate, polycaprolactone diol di (meth) acrylate, polybutadiene diol di (meth) acrylate, and the like.
Examples of the compound having 3 or more functions in the ester compound include pentaerythritol tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, propylene oxide-added trimethylolpropane tri (meth) acrylate, ethylene oxide-added trimethylolpropane tri (meth) acrylate, caprolactone-modified trimethylolpropane tri (meth) acrylate, ethylene oxide-added isocyanuric acid tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, glycerol tri (meth) acrylate, propylene oxide-added glycerol tri (meth) acrylate, and tri (meth) acryloyloxyethyl phosphate.
Examples of the epoxy (meth) acrylate include epoxy (meth) acrylates obtained by reacting an epoxy compound with (meth) acrylic acid in the presence of a basic catalyst according to a conventional method.
Examples of the epoxy compound to be used as a raw material for synthesizing the above epoxy (meth) acrylate include bisphenol a type epoxy resins, bisphenol F type epoxy resins, bisphenol S type epoxy resins, 2' -diallylbisphenol a type epoxy resins, hydrogenated bisphenol type epoxy resins, propylene oxide-converted bisphenol a type epoxy resins, resorcinol type epoxy resins, biphenyl type epoxy resins, thioether type epoxy resins, diphenylether type epoxy resins, dicyclopentadiene type epoxy resins, naphthalene type epoxy resins, phenol novolac type epoxy resins, o-cresol novolac type epoxy resins, dicyclopentadiene novolac type epoxy resins, biphenol novolac type epoxy resins, naphthol novolac type epoxy resins, glycidyl amine type epoxy resins, alkyl polyhydric alcohol type epoxy resins, rubber modified epoxy resins, glycidyl ester compounds, Bisphenol a type episulfide resins, and the like.
Examples of the commercially available products of the bisphenol A epoxy resin include jER828EL, jER1001, jER1004 (both manufactured by Mitsubishi chemical corporation), EPICLON 850-S (manufactured by DIC corporation), and the like.
Examples of commercially available products of the bisphenol F type epoxy resin include jER806 and jER4004 (both manufactured by Mitsubishi chemical corporation).
Examples of the commercially available products of the bisphenol S type epoxy resin include EPICLON EXA1514 (available from DIC).
Examples of commercially available products of the 2, 2' -diallylbisphenol A-type epoxy resin include RE-810 NM (manufactured by Nippon chemical Co., Ltd.).
Examples of commercially available products of the hydrogenated bisphenol epoxy resin include EPICLON EXA7015 (available from DIC).
Examples of commercially available products of the above propylene oxide-added bisphenol A epoxy resin include EP-4000S (manufactured by ADEKA).
Examples of commercially available products of the above resorcinol type epoxy resins include EX-201 (manufactured by Nagase Chemtex).
Examples of the commercially available biphenyl type epoxy resin include jERYX-4000H (manufactured by Mitsubishi chemical corporation).
Examples of commercially available products of the thioether-type epoxy resin include YSLV-50 TE (manufactured by Nippon Tekken chemical Co., Ltd.).
Examples of commercially available products of the above diphenyl ether type epoxy resins include YSLV-80 DE (manufactured by Nippon Tekken chemical Co., Ltd.).
Examples of commercially available products of the above-mentioned dicyclopentadiene type epoxy resins include EP-4088S (manufactured by ADEKA).
Examples of the naphthalene epoxy resin include EPICLON HP4032 and EPICLON EXA-4700 (both DIC).
Examples of the commercially available phenol novolac epoxy resin include EPICLON-770 (available from DIC).
Examples of the commercially available products of the o-cresol novolak type epoxy resin include EPICLON-670-EXP-S (available from DIC).
Examples of commercially available products of the dicyclopentadiene novolak type epoxy resin include EPICLON HP7200 (available from DIC).
Examples of the commercially available products of the above-mentioned biphenyl novolak type epoxy resin include NC-3000P (manufactured by Nippon chemical Co., Ltd.).
Examples of the commercially available products of the naphthol novolac type epoxy resins include ESN-165S (manufactured by Nippon iron Co., Ltd.).
Examples of commercially available products of the glycidyl amine type epoxy resin include JeR630 (manufactured by Mitsubishi chemical corporation), EPICLON 430 (manufactured by DIC corporation), and TETRAD-X (manufactured by Mitsubishi gas chemical corporation).
Examples of commercially available products of the above-mentioned alkyl polyol type epoxy resin include ZX-1542 (available from Nippon Tekken chemical Co., Ltd.), EPICLON 726 (available from DIC Co., Ltd.), EPOLIT 80MFA (available from Kyoho chemical Co., Ltd.), DENACOL EX-611 (available from Nagase Chemtex Co., Ltd.), and the like.
Examples of commercially available products of the rubber-modified epoxy resin include YR-450, YR-207 (both manufactured by Nippon Tekken chemical Co., Ltd.), EPOLEAD PB (manufactured by Daiiol Co., Ltd.).
Examples of commercially available products of the glycidyl ester compounds include DENACOL EX-147 (manufactured by Nagase Chemtex).
Examples of commercially available products of the bisphenol A type episulfide resin include jERYL-7000 (manufactured by Mitsubishi chemical corporation).
Examples of other commercially available products of the above epoxy resins include YDC-1312, YSLV-80 XY, YSLV-90 CR (all manufactured by Nippon Tekken chemical Co., Ltd.), XAC4151 (manufactured by Asahi Kasei Co., Ltd.), jER1031, jER1032 (all manufactured by Mitsubishi chemical Co., Ltd.), EXA-7120 (manufactured by DIC Co., Ltd.), and TEPIC (manufactured by Nissan chemical Co., Ltd.).
Examples of commercially available products of the above EPOXY (meth) acrylate include EBECRYL860, EBECRYL3200, EBECRYL3201, EBECRYL3412, EBECRYL3600, EBECRYL3700, EBECRYL3701, EBECRYL3702, EBECRYL3703, EBECRYL3800, EBECRYL6040, EBECRYL RDX63182 (both manufactured by DAICEL. ALLNEX LTD. Co., Ltd.), EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020 (both manufactured by Nippon chemical industries Co., Ltd.), NACOSTER M-600A, EPXY ESTER 40EM, EPXY ESTER 70PA, EPOXER 200PA, EPXY ESTER 80A, EPOXY ESTER 3002M, EPOXEPOXER 3002A, EPOXY ESTER 1600A, EPOXY ESTER 3000, DEXY 863000, DEESTER 3000 (DEESLEX.A., DES.S.S.K.), DEESTER 3000, DEESOL 3000, and DEESEL.S.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.K.
The urethane (meth) acrylate can be obtained by, for example, reacting 1 equivalent of a compound having 2 isocyanate groups with 2 equivalents of a (meth) acrylic acid derivative having a hydroxyl group in the presence of a catalytic amount of a tin-based compound.
Examples of the isocyanate which is a raw material of the urethane (meth) acrylate include isophorone diisocyanate, 2, 4-toluene diisocyanate, 2, 6-toluene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, diphenylmethane-4, 4' -diisocyanate (MDI), hydrogenated MDI, polymeric MDI, 1, 5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate, Xylylene Diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris (isocyanatophenyl) thiophosphate, tetramethylxylene diisocyanate, 1,6, 11-undecane triisocyanate, and the like.
Further, as the isocyanate, for example, an isocyanate compound having an extended chain obtained by a reaction of a polyol such as ethylene glycol, glycerin, sorbitol, trimethylolpropane, (poly) propylene glycol, carbonate diol, polyether diol, polyester diol, polycaprolactone diol, or the like with an excess amount of isocyanate can be used.
Examples of the (meth) acrylic acid derivative having a hydroxyl group which is a raw material of the urethane (meth) acrylate include mono (meth) acrylates of diols such as ethylene glycol, propylene glycol, 1, 3-propanediol, 1, 3-butanediol, 1, 4-butanediol, and polyethylene glycol, mono (meth) acrylates or di (meth) acrylates of triols such as trimethylolethane, trimethylolpropane, and glycerol, and epoxy (meth) acrylates such as bisphenol a type epoxy (meth) acrylates.
Examples of commercially available products of the above urethane (meth) acrylates include M-1100, M-1200, M-1210, M-1600 (all manufactured by Toyo Synthesis Co., Ltd.), EBECRYL230, EBECRYL270, EBECRYL4858, EBECRYL8402, EBECRYL8411, EBECRYL8412, EBECRYL8413, EBECRYL4, EBECRYL8803, EBECRYL8807, EBECRYL9260, EBECRYL1290, EBECRYL5129, EBECRYL4842, EBECRYL210, EBECRYL4827, EBECRYL6700, EBECRYL220, EBECRYL2220, KRM7735, KRM-8295 (all manufactured by DAECRYL NETRD. RTM.), AresUN-9000H, Aresin-9000A, AresUN-7100, AresRtHA 7156, AresRYL 3931, AresRYL 3-70, AresRYL 3, AresRYL 3970, AresRYL 3, AresRYL 483, AresRYL 3, AresRYL 340, AresRYL 3, ARESU-3, ARESRYL 340, ARESRYL 483, ARESRYL 340, ARESU-3, ARESRYL 483, ARESRYL 340, ARESRYL 1, ARESU-3, ARESU-ASU-ASE, ARESU-ASE, ARESRYL 1, ARESU-ASE, ARESRYL 1, ARESU-ASE, ARESRYL 1, ARESU-ASE, ARESRYL 1, ARESR-ASE, ARESU-ASE, ARESR-ASR-ASE, ARESU-ASE.S.S.S.S.S.S.S.S.E.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S., U-2061 BA, UA-340P, UA-4100, UA-4000, UA-4200, UA-4400, UA-5201P, UA-7100, UA-7200, UA-W2A (all manufactured by Ningzhou chemical industries Co., Ltd.), AI-600, AH-600, AT-600, UA-101I, UA-101T, UA-306H, UA-306I, UA-306T (all manufactured by Kyowa chemical Co., Ltd.), and the like.
In addition, other radical polymerizable compounds than those described above can also be suitably used.
Examples of the other radical polymerizable compounds include (meth) acrylamide compounds such as N, N-dimethyl (meth) acrylamide, N- (meth) acryloylmorpholine, N-hydroxyethyl (meth) acrylamide, N-diethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, and N, N-dimethylaminopropyl (meth) acrylamide, and vinyl compounds such as styrene, α -methylstyrene, N-vinylpyrrolidone, and N-vinylcaprolactone.
The radical polymerizable compound preferably contains a monofunctional radical polymerizable compound and a polyfunctional radical polymerizable compound from the viewpoint of adjusting curability and the like. When only the monofunctional radical polymerizable compound is used, the resultant photo-moisture-curable resin composition may have poor curability, and when only the polyfunctional radical polymerizable compound is used, the resultant photo-moisture-curable resin composition may have poor viscosity. Among these, it is more preferable to use a compound having a nitrogen atom in the molecule as the monofunctional radical polymerizable compound and a urethane (meth) acrylate as the polyfunctional radical polymerizable compound in combination. The polyfunctional radical polymerizable compound is preferably 2-functional or 3-functional, and more preferably 2-functional.
When the radical polymerizable compound contains the monofunctional radical polymerizable compound and the polyfunctional radical polymerizable compound, the preferable lower limit of the content of the polyfunctional radical polymerizable compound is 2 parts by weight, and the preferable upper limit is 30 parts by weight, based on 100 parts by weight of the total of the monofunctional radical polymerizable compound and the polyfunctional radical polymerizable compound. When the content of the polyfunctional radical polymerizable compound is less than 2 parts by weight, the resultant photo-moisture-curable resin composition may have poor curability. When the content of the polyfunctional radical polymerizable compound is more than 30 parts by weight, the resulting photo-moisture-curable resin composition may have poor viscosity. The lower limit of the content of the polyfunctional radical polymerizable compound is more preferably 5 parts by weight, and the upper limit is more preferably 20 parts by weight.
The light moisture-curable resin composition of the present invention contains a moisture-curable urethane resin. In the moisture-curable urethane resin, an isocyanate group in a molecule reacts with moisture in the air or in an adherend to be cured. The obtained moisture-curable resin composition is superior in rapid curability to a moisture-curable resin composition obtained by using a compound having a crosslinkable silyl group or the like as a moisture-curable component.
The moisture-curable urethane resin may contain only 1 isocyanate group in 1 molecule, or may contain 2 or more isocyanate groups. Among these, a urethane prepolymer having isocyanate groups at both ends is preferable.
The urethane prepolymer can be obtained by reacting a polyol compound having 2 or more hydroxyl groups in 1 molecule with a polyisocyanate compound having 2 or more isocyanate groups in 1 molecule.
The reaction of the polyol compound with the polyisocyanate compound is usually carried out in such a manner that the molar ratio of the hydroxyl group (OH) in the polyol compound to the isocyanate group (NCO) in the polyisocyanate compound is 2.0 to 2.5.
As the polyol compound, known polyol compounds generally used in the production of polyurethane can be used, and examples thereof include polyester polyol, polyether polyol, alkylene-containing polyol, polycarbonate polyol and the like. These polyol compounds may be used alone, or 2 or more of them may be used in combination.
Examples of the polyester polyol include a polyester polyol obtained by reacting a polycarboxylic acid with a polyol, and a poly-e-caprolactone polyol obtained by ring-opening polymerization of e-caprolactone.
Examples of the polycarboxylic acid which is a raw material of the polyester polyol include terephthalic acid, isophthalic acid, 1, 5-naphthalenedicarboxylic acid, 2, 6-naphthalenedicarboxylic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, decamethylenedicarboxylic acid, and dodecamethylenedicarboxylic acid.
Examples of the polyhydric alcohol which is a raw material of the polyester polyol include ethylene glycol, propylene glycol, 1, 3-propanediol, 1, 4-butanediol, neopentyl glycol, 1, 5-pentanediol, 1, 6-hexanediol, diethylene glycol, and cyclohexanediol.
Examples of the polyether polyol include ring-opened polymers of ethylene glycol, propylene glycol, tetrahydrofuran and 3-methyltetrahydrofuran, random copolymers or block copolymers of these and derivatives thereof, and bisphenol-type polyoxyalkylene modifications.
The modified bisphenol polyoxyalkylene is a polyether polyol obtained by addition reaction of an active hydrogen moiety of a bisphenol molecular skeleton and an alkylene oxide (e.g., ethylene oxide, propylene oxide, butylene oxide, isobutylene oxide, etc.), and may be a random copolymer or a block copolymer.
The bisphenol-type polyoxyalkylene modified product is preferably obtained by adding 1 or 2 or more kinds of alkylene oxide to both ends of a bisphenol-type molecular skeleton. The bisphenol type is not particularly limited, and examples thereof include a type, F type, and S type, and bisphenol a type is preferable.
Examples of the polyalkylene polyol include polybutadiene polyol, hydrogenated polybutadiene polyol, and hydrogenated polyisoprene polyol.
Examples of the polycarbonate polyol include polyhexamethylene carbonate polyol and polycyclohexane dimethylene carbonate polyol.
Examples of the polyisocyanate compound include diphenylmethane diisocyanate, liquid modified diphenylmethane diisocyanate, polymeric MDI (methane diisocyanate), toluene diisocyanate, naphthalene-1, 5-diisocyanate, and the like. Among them, diphenylmethane diisocyanate and modified products thereof are preferable from the viewpoint of low vapor pressure and toxicity and easy handling. The polyisocyanate-based compounds may be used alone or in combination of 2 or more.
The moisture-curable urethane resin is preferably a urethane resin obtained using a polyol compound having a structure represented by the following formula (1). By using a polyol compound having a structure represented by the following formula (1), a composition having excellent adhesiveness and a cured product having good flexibility and elongation can be obtained, and a urethane resin having excellent compatibility with the radical polymerizable compound can be obtained.
Among them, polyether polyols containing propylene glycol, a ring-opening polymerization compound of a Tetrahydrofuran (THF) compound, and a ring-opening polymerization compound of a tetrahydrofuran compound having a substituent such as a methyl group are preferably used.
[ solution 1]
Figure BDA0003331969690000121
In the formula (1), R represents hydrogen, methyl or ethyl, n is an integer of 1-10, L is an integer of 0-5, and m is an integer of 1-500. n is preferably 1 to 5, L is preferably 0 to 4, and m is preferably 50 to 200.
The case where L is 0 means a case where the carbon bonded to R is directly bonded to oxygen.
Further, the moisture-curable urethane resin may have a radical polymerizable functional group.
The radical polymerizable functional group that the moisture-curable urethane resin may have is preferably a group having an unsaturated double bond, and particularly from the viewpoint of reactivity, a (meth) acryloyl group is more preferable.
The moisture-curable urethane resin having a radical polymerizable functional group is not contained in a radical polymerizable compound, and is treated as a moisture-curable urethane resin.
The weight average molecular weight of the moisture-curable urethane resin preferably has a lower limit of 800 and an upper limit of 1 ten thousand. When the weight average molecular weight of the moisture-curable urethane resin is less than 800, the crosslinking density may be increased, and the flexibility may be impaired. When the weight average molecular weight of the moisture-curable urethane resin is more than 1 ten thousand, the obtained moisture-curable resin composition may have poor coatability. The moisture-curable urethane resin has a weight average molecular weight of more preferably 2000 as a lower limit, more preferably 8000 as an upper limit, still more preferably 3000 as a lower limit, and still more preferably 6000 as an upper limit.
In the present specification, the weight average molecular weight is a value measured by Gel Permeation Chromatography (GPC) and obtained by polystyrene conversion. Examples of the column used in the measurement of the weight average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa Denko K.K.). Examples of the solvent used in GPC include tetrahydrofuran.
The content of the moisture-curable urethane resin is preferably 20 parts by weight at the lower limit and 90 parts by weight at the upper limit, based on 100 parts by weight of the total of the radical polymerizable compound and the moisture-curable urethane resin. If the content of the moisture-curable urethane resin is less than 20 parts by weight, the moisture curability of the resulting photo-moisture-curable resin composition may be poor. When the content of the moisture-curable urethane resin is more than 90 parts by weight, the resulting moisture-curable resin composition may have poor photocurability. The content of the moisture-curable urethane resin is more preferably 30 parts by weight at the lower limit, more preferably 75 parts by weight at the upper limit, still more preferably 41 parts by weight at the lower limit, and still more preferably 70 parts by weight at the upper limit.
The moisture-curable resin composition of the present invention contains a photo radical polymerization initiator.
Examples of the photo radical polymerization initiator include benzophenone-based compounds, acetophenone-based compounds, acylphosphine oxide-based compounds, titanocene-based compounds, oxime ester-based compounds, benzoin ether-based compounds, thioxanthone, etc., and acylphosphine oxide-based compounds are preferable from the viewpoint of obtaining a composition particularly excellent in photocurability (deep curing ability). The photo radical polymerization initiator is preferably a photo radical polymerization initiator that can be exposed to light by irradiation with light having a wavelength of 370 to 450nm as described above.
Examples of the acylphosphine oxide compound include bis (2,4, 6-trimethylbenzoyl) -phenylphosphine oxide, 2,4, 6-trimethylbenzoyl diphenylphosphine oxide, and the like.
Examples of commercially available products of the photo radical polymerization initiator include IRGACURE184, IRGACURE369, IRGACURE379, IRGACURE651, IRGACURE784, IRGACURE819, IRGACURE907, IRGACURE2959, IRGACURE4265, IRGACURE OXE01, LucirinTPO, (both manufactured by BASF Japan), benzoin methyl ether, benzoin ethyl ether, and benzoin isopropyl ether (all manufactured by tokyo chemical industries).
The lower limit of the content of the photo radical polymerization initiator is preferably 0.01 part by weight, and the upper limit is preferably 10 parts by weight, based on 100 parts by weight of the radical polymerizable compound. If the content of the photo radical polymerization initiator is less than 0.01 parts by weight, the resulting photo moisture-curable resin composition may not be sufficiently photo-cured. When the content of the photo radical polymerization initiator is more than 10 parts by weight, the storage stability of the resulting photo moisture-curable resin composition may be lowered. The content of the photo radical polymerization initiator is more preferably 0.1 part by weight in the lower limit and 5 parts by weight in the upper limit.
The moisture-curable resin composition of the present invention may contain a sensitizer.
The moisture-curable resin composition of the present invention contains the sensitizer, and thus a moisture-curable resin composition having high sensitivity and excellent photocurability can be obtained. The sensitizer is preferably one which exerts a sensitizing effect by being irradiated with light having a wavelength of 370 to 450nm as described above.
The sensitizer preferably has a sufficient light absorption band in the ultraviolet and visible region, and therefore preferably contains a compound having at least one skeleton selected from a benzophenone skeleton, an anthracene skeleton, an anthraquinone skeleton, a coumarin skeleton, a thioxanthone skeleton, and a phthalocyanine skeleton, and more preferably contains a compound having at least one skeleton selected from an anthracene skeleton, an anthraquinone skeleton, and a thioxanthone skeleton. These compounds can also be used as the photo radical polymerization initiator.
Examples of the compound having a benzophenone skeleton include benzophenone, 2, 4-dichlorobenzophenone, 4 '-bis (dimethylamino) benzophenone, 4' -bis (diethylamino) benzophenone, and the like.
Examples of the compound having an anthracene skeleton include 9, 10-dibutoxyanthracene, 9, 10-dipropoxyanthraquinone, and 9, 10-ethoxyanthraquinone.
Examples of the compound having an anthraquinone skeleton include 2-ethylanthraquinone, 1-methylanthraquinone, 1, 4-dihydroxyanthraquinone, and 2- (2-hydroxyethoxy) -anthraquinone.
Examples of the compound having a coumarin skeleton include 7-diethylamino-4-methylcoumarin.
Examples of the compound having a thioxanthone skeleton include 2, 4-diethylthioxanthone, 2-chlorothioxanthone, 4-isopropylthioxanthone, and 1-chloro-4-propylthioxanthone.
Examples of the compound having a phthalocyanine skeleton include phthalocyanine.
Among these sensitizers, it is preferable to use at least one of 4,4 '-bis (dimethylamino) benzophenone and 4, 4' -bis (diethylamino) benzophenone from the viewpoint that the resulting moisture-curable resin composition is a composition particularly excellent in curability of the light shielding portion.
The content of the sensitizer is preferably 2 parts by weight at the lower limit and 50 parts by weight at the upper limit with respect to 100 parts by weight of the photopolymerization initiator. If the content of the sensitizer is less than 2 parts by weight, the sensitizing effect may not be sufficiently exhibited. If the content of the sensitizer is more than 50 parts by weight, the storage stability of the resulting moisture-curable resin composition may be lowered. A more preferable lower limit of the content of the above sensitizer is 5 parts by weight, and a more preferable upper limit is 40 parts by weight.
The moisture-curable resin composition of the present invention may contain a filler in view of adjusting the coatability, shape retention property, and the like of the resulting moisture-curable resin composition. By containing the filler, the light/moisture-curable resin composition of the present invention has appropriate thixotropy, and can sufficiently maintain the shape after application.
The lower limit of the primary particle diameter of the filler is preferably 1nm, and the upper limit is preferably 50 nm. If the primary particle diameter of the filler is less than 1nm, the resulting moisture-curable resin composition may have poor coatability. If the primary particle diameter of the filler is larger than 50nm, the shape retention property of the resulting photo-moisture-curable resin composition after coating may be poor. The lower limit of the primary particle diameter of the filler is more preferably 5nm, the upper limit is more preferably 30nm, the lower limit is more preferably 10nm, and the upper limit is more preferably 20 nm.
The primary PARTICLE size of the filler can be measured by dispersing the filler in a solvent (water, organic solvent, etc.) using NICOMP 380ZLS (manufactured by PARTICLE SIZING SYSTEMS).
The filler may be present in the moisture-curable resin composition of the present invention as secondary particles (particles in which a plurality of primary particles are aggregated), and the particle diameter of such secondary particles preferably has a lower limit of 5nm, a higher limit of 500nm, a higher limit of 10nm, and a higher limit of 100 nm. The particle diameter of the secondary particles of the filler can be measured by observing the light/moisture-curable resin composition of the present invention or the cured product thereof using a Transmission Electron Microscope (TEM).
The filler is preferably an inorganic filler, and examples thereof include silica, talc, titanium oxide, zinc oxide, and calcium carbonate. Among these, silica is preferable because the obtained moisture-curable resin composition has excellent UV light transmittance. These fillers may be used alone, or 2 or more of them may be used in combination.
The filler is preferably subjected to a hydrophobic surface treatment. The resulting moisture-curable resin composition has more excellent shape retention properties after application by the hydrophobic surface treatment.
Examples of the hydrophobic surface treatment include silylation, alkylation, and epoxyation. Among them, from the viewpoint of excellent effect of improving the shape retention property, the silylation treatment is preferable, and the trimethylsilylation treatment is more preferable.
Examples of the method of subjecting the filler to hydrophobic surface treatment include a method of treating the surface of the filler with a surface treatment agent such as a silane coupling agent.
Specifically, for example, the trimethylsilylated silica can be produced by a method such as synthesizing silica by a sol-gel method or the like, and spraying hexamethyldisilazane while the silica is fluidized; a method in which silica is added to an organic solvent such as alcohol or toluene, hexamethyldisilazane and water are further added, and then the water and the organic solvent are evaporated and dried by an evaporator.
The preferable lower limit of the content of the filler is 0.1 part by weight and the preferable upper limit is 20 parts by weight in 100 parts by weight of the entire moisture-curable resin composition of the present invention. If the content of the filler is less than 0.1 part by weight, the shape retention property of the resulting photo-moisture-curable resin composition after coating may be poor. If the content of the filler is more than 20 parts by weight, the resulting moisture-curable resin composition may have poor coatability. The content of the filler is more preferably 0.5 part by weight at the lower limit, more preferably 15 parts by weight at the upper limit, still more preferably 1 part by weight at the lower limit, still more preferably 12 parts by weight at the upper limit, and particularly preferably 2 parts by weight at the lower limit.
The moisture-curable resin composition of the present invention may further contain additives such as an ionic liquid, a solvent, metal-containing particles, and a reactive diluent, if necessary.
Examples of the method for producing the moisture-curable resin composition of the present invention include a method of mixing a radical polymerizable compound, a moisture-curable urethane resin, a photo radical polymerization initiator, a light-screening agent, and additives added as needed, using a mixer such as a homomixer, a universal mixer, a planetary mixer, a kneader, or a three-roll machine.
The moisture-curable resin composition of the present invention can be cured sufficiently by curing the composition by moisture through rapid curing by light irradiation.
As the light source used for photocuring the moisture-curable resin composition of the present invention, not only a high-pressure mercury lamp and a metal halide lamp that are generally used but also an LED type light source can be used.
The moisture-curable resin composition of the present invention preferably has an optical density (OD value) of 1mm or more of a cured product after curing. If the OD value is less than 1, light-shielding properties may be insufficient, light may leak when used in a display device, and high contrast may not be obtained. The OD value is more preferably 1.5 or more.
The higher the OD value, the better, if the OD value is increased, if a too large amount of light-shading agent is added to increase the OD value, the workability may be deteriorated due to thickening, and therefore, in order to balance the amount of light-shading agent added, the preferable upper limit of the OD value of the cured product is 4.
The OD value of the light/moisture-curable resin composition after curing can be measured using an optical densitometer. The cured product for measuring the OD value can be irradiated with 500mJ/cm using a high-pressure mercury lamp or the like2Ultraviolet rays of (4).
The preferred lower limit of the viscosity of the light/moisture-curable resin composition of the present invention measured at 25 ℃ and 1rpm with a cone-plate viscometer is 50 pas, and the preferred upper limit is 500 pas. When the viscosity is less than 50 pas or more than 500 pas, handling properties when the light/moisture-curable resin composition is applied to an adherend such as a substrate may be deteriorated when the composition is used as an adhesive for electronic components or an adhesive for display elements. The lower limit of the viscosity is more preferably 80 pas, the upper limit is more preferably 300 pas, and the upper limit is more preferably 200 pas.
The preferable lower limit of the thixotropic index of the moisture-curable resin composition of the present invention is 1.3, and the preferable upper limit is 5.0. When the thixotropic index is less than 1.3 or more than 5.0, the workability when applying the light/moisture-curable resin composition to an adherend such as a substrate may be deteriorated when the light/moisture-curable resin composition is used as an adhesive for electronic components or an adhesive for display elements. A more preferable lower limit and a more preferable upper limit of the thixotropic index are 1.5 and 4.0, respectively.
In the present specification, the thixotropic index is a value obtained by dividing a viscosity measured at 25 ℃ and 1rpm with a cone and plate viscometer by a viscosity measured at 25 ℃ and 10rpm with a cone and plate viscometer.
The moisture-curable resin composition of the present invention can be used particularly preferably as an adhesive for electronic components and an adhesive for display elements. An adhesive for electronic parts produced using the moisture-curable resin composition of the present invention and an adhesive for display elements produced using the moisture-curable resin composition of the present invention are also one aspect of the present invention.
Effects of the invention
The present invention can provide a light-moisture-curable resin composition having excellent light-shielding properties and adhesion properties.
Drawings
Fig. 1(a) is a schematic view showing a sample for evaluation of adhesiveness when viewed from above, and fig. 1(b) is a schematic view showing a sample for evaluation of adhesiveness when viewed from the lateral direction.
Detailed Description
The present invention will be described in further detail below with reference to examples, but the present invention is not limited to these examples. Further, the present invention can provide an adhesive for electronic components and an adhesive for display elements, which are produced using the light/moisture curable resin composition.
Synthesis example 1 (preparation of urethane prepolymer A)
100 parts by weight of polytetramethylene ether glycol ("PTMG-2000" manufactured by Mitsubishi chemical corporation) as a polyol and 0.01 part by weight of dibutyltin dilaurate were charged into a 500 mL-capacity separable flask, and stirred at 100 ℃ for 30 minutes under vacuum (20mmHg or less) and mixed. Subsequently, 26.5 parts by weight of Pure MDI (manufactured by Nissan Co., Ltd.) as a diisocyanate was added thereto under normal pressure, and the mixture was stirred at 80 ℃ for 3 hours to react, thereby obtaining a urethane prepolymer A (weight-average molecular weight 2700).
Synthesis example 2 (preparation of urethane prepolymer B)
100 parts by weight of polypropylene glycol ("EXCENOL 2020", Asahi glass Co., Ltd.) as a polyol and 0.01 part by weight of dibutyltin dilaurate were charged into a 500mL separable flask, and the mixture was stirred at 100 ℃ for 30 minutes under vacuum (20mmHg or less) and mixed. Subsequently, 26.5 parts by weight of Pure MDI (manufactured by Nissan Co., Ltd.) as a diisocyanate was added thereto under normal pressure, and the mixture was stirred at 80 ℃ for 3 hours to react, thereby obtaining a urethane prepolymer B (weight average molecular weight 2900).
Synthesis example 3 (preparation of urethane prepolymer C)
Into a reaction vessel containing urethane prepolymer A obtained in the same manner as in Synthesis example 1, 1.3 parts by weight of hydroxyethyl methacrylate and 0.14 parts by weight of N-nitrosophenylhydroxylamine aluminum salt (manufactured by Wako pure chemical industries, Ltd. "Q-1301") as a polymerization inhibitor were added, and the mixture was stirred and mixed at 80 ℃ for 1 hour under a nitrogen stream to obtain urethane prepolymer C having an isocyanate group and a methacryloyl group at the molecular terminal (weight-average molecular weight 3100).
Examples 1 to 16 and comparative examples 1 and 2
The materials were stirred by a planetary stirring apparatus (manufactured by Thinky corporation, "あわとり tylan") in accordance with the mixing ratios shown in tables 1 and 2, and then uniformly mixed by a ceramic three-roll mill to obtain moisture-curable resin compositions of examples 1 to 16 and comparative examples 1 and 2.
In table 1, "urethane prepolymer a" is a urethane prepolymer having isocyanate groups at both ends described in synthesis example 1, "urethane prepolymer B" is a urethane prepolymer having isocyanate groups at both ends described in synthesis example 2, and "urethane prepolymer C" is a urethane prepolymer having isocyanate groups and methacryloyl groups at molecular ends described in synthesis example 3.
< evaluation >
The following evaluations were made for each of the moisture-curable resin compositions obtained in examples and comparative examples. The results are shown in tables 1 and 2.
(light-blocking Property (OD value))
Each of the moisture-curable resin compositions obtained in examples and comparative examples was coated on a release polyethylene terephthalate (PET) sheet having a thickness of 1mm and containing Teflon (registered trademark) chips as a spacer, the release PET was further superposed thereon, and the resultant was pressed with a glass to form a uniform thickness, followed by irradiating 500mJ/cm by a high-pressure mercury lamp2Thereby photo-curing the photo moisture-curable resin composition.
Subsequently, it was moisture-cured by placing it at night, thereby obtaining a sample for evaluation of light-shielding property with a thickness of 1 mm.
The obtained light-shielding property evaluation sample was measured for optical density (OD value) using an optical densitometer ("spectrometer" manufactured by X-rite Co.).
(adhesiveness)
Each of the moisture-curable resin compositions obtained in examples and comparative examples was coated on a polycarbonate substrate with a width of about 2mm using a dispenser. Subsequently, 500mJ/cm was irradiated using a high-pressure mercury lamp2Thereby photo-curing the moisture curable resin composition.
Subsequently, a glass plate was attached to the polycarbonate substrate and placed at night to cure moisture, thereby obtaining a sample for evaluation of adhesiveness.
Fig. 1 shows a schematic view showing a case where the sample for adhesiveness evaluation is observed from above (fig. 1(a)), and a schematic view showing a case where the sample for adhesiveness evaluation is observed from a lateral direction (fig. 1 (b)).
The prepared sample for adhesion evaluation was stretched at a speed of 5mm/sec in the shear direction using a tensile tester to measure the strength at the time of peeling of the substrate.
(deep curing)
Each of the moisture-curable resin compositions obtained in examples and comparative examples was coated on a polycarbonate substrate with a width of about 2mm using a dispenser. Subsequently, 500mJ/cm was irradiated using a high-pressure mercury lamp2The sample for deep curing evaluation was prepared by photocuring the moisture-curable resin composition with ultraviolet rays of (1). In the case of a sample for deep curing evaluation obtained by wiping with a nonwoven fabric impregnated with acetone ("Bemcot" manufactured by asahi chemical fiber company), a sample in which the entire cured product was easily removed from the substrate (no deep curing occurred) was evaluated as "x", a sample in which a part of the cured product remained on the substrate (a part of the cured product was deep cured) was evaluated as "Δ", a sample in which a large part of the cured product remained on the substrate (a large part of the cured product was deep cured) was evaluated as "o", and a sample in which the cured product was completely not removed from the substrate (deep curing occurred) was evaluated as "x", thereby evaluating the deep curing property.
[ Table 1]
Figure BDA0003331969690000211
[ Table 2]
Figure BDA0003331969690000221
Industrial applicability
The present invention can provide a light-moisture-curable resin composition having excellent light-shielding properties and adhesion properties. Further, the present invention can provide an adhesive for electronic components and an adhesive for display elements, which are produced using the light/moisture curable resin composition.
Description of the symbols
1 polycarbonate resin substrate
2 photo-moisture-curable resin composition
3 glass plate

Claims (10)

1. An adhesive for electronic parts, characterized by containing a radical polymerizable compound, a moisture-curable urethane resin, a photo radical polymerization initiator and a light-shading agent,
the moisture-curable urethane resin contains 1 or 2 or more isocyanate groups in 1 molecule, and the OD value of a cured product having a thickness of 1mm after curing is 1 or more.
2. The adhesive for electronic parts according to claim 1, wherein the radical polymerizable compound comprises a monofunctional radical polymerizable compound and a polyfunctional radical polymerizable compound.
3. The adhesive for electronic parts according to claim 1 or 2, wherein the light-shading agent is iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, or resin-coated carbon black.
4. The adhesive for electronic parts according to claim 1 or 2, wherein the photo radical polymerization initiator is an acylphosphine oxide-based compound.
5. The adhesive for electronic components according to claim 1 or 2, which contains a filler having a primary particle diameter of 1nm to 50 nm.
6. An adhesive for display elements, characterized by containing a radical polymerizable compound, a moisture-curable urethane resin, a photo-radical polymerization initiator and a light-shading agent,
the moisture-curable urethane resin contains 1 or 2 or more isocyanate groups in 1 molecule, and the OD value of a cured product having a thickness of 1mm after curing is 1 or more.
7. The adhesive for display elements according to claim 6, wherein the radical polymerizable compound comprises a monofunctional radical polymerizable compound and a polyfunctional radical polymerizable compound.
8. The adhesive for display elements according to claim 6 or 7, wherein the light-shading agent is iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, or resin-coated carbon black.
9. The adhesive for display elements according to claim 6 or 7, wherein the photo radical polymerization initiator is an acylphosphine oxide compound.
10. The adhesive for display elements according to claim 6 or 7, which contains a filler having a primary particle diameter of 1nm to 50 nm.
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