CN111574928A - Light-moisture-curable resin composition, adhesive for electronic component, and adhesive for display element - Google Patents

Light-moisture-curable resin composition, adhesive for electronic component, and adhesive for display element Download PDF

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CN111574928A
CN111574928A CN202010445909.3A CN202010445909A CN111574928A CN 111574928 A CN111574928 A CN 111574928A CN 202010445909 A CN202010445909 A CN 202010445909A CN 111574928 A CN111574928 A CN 111574928A
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moisture
resin composition
adhesive
meth
curable resin
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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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • 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
    • 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
    • C08G18/088—Removal of water or carbon dioxide from the reaction mixture or reaction components
    • C08G18/0885—Removal of water or carbon dioxide from the reaction mixture or reaction components using additives, e.g. absorbing agents
    • 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
    • C08G18/40—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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/014—Stabilisers against oxidation, heat, light or ozone
    • 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
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C—CHEMISTRY; METALLURGY
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Polymerisation Methods In General (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The purpose of the present invention is to provide a light-moisture-curable resin composition having excellent storage stability and adhesion. 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 curing resin composition contains a free radical polymerization compound, a moisture curing polyurethane resin, a light free radical polymerization initiator and a water removing agent.

Description

Light-moisture-curable resin composition, adhesive for electronic component, and adhesive for display element
This application is a divisional application of the invention entitled "light-moisture-curable resin composition, adhesive for electronic parts, and adhesive for display elements" in the state of national application No. 201580001997.5 (international application No. PCT/JP2015/051348) at the time of entering china at 25.3.2016.
Technical Field
The present invention relates to a moisture-curable resin composition having excellent storage stability and adhesiveness. 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, sealing of the liquid crystal layer and the light-emitting layer is generally performed; photocurable resin compositions are used for bonding substrates, optical films, protective films, and various members.
However, in the modern times in which various mobile devices with display elements such as mobile phones and mobile game machines are widespread, the miniaturization of the display elements is the most demanding issue, and as a method for miniaturization, narrowing of the frame of the image display portion (hereinafter, also referred to as narrow frame design) has been carried out. However, in the narrow-frame design, there is a problem that the photocurable resin composition applied to the part not reached by light is insufficiently cured as a result of the application of the photocurable resin composition to the part not reached by light. Therefore, a photo-thermal curable resin composition is used as a resin composition that can be sufficiently cured even when applied to a portion not reached by light, and photo-curing and thermal curing are also used in combination.
As a method for curing a resin composition without heating at a high temperature, patent document 1 discloses the following method: a light moisture-curable resin composition containing a polyurethane prepolymer having at least 1 isocyanate group and at least 1 (meth) acryloyl group in the molecule is used, and light curing and moisture curing are combined. However, the moisture-curable resin composition disclosed in patent document 1 has a problem that it is difficult to achieve both storage stability and adhesiveness.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open No. 2008-274131
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 storage stability and adhesion. 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 curing resin composition contains a free radical polymerization compound, a moisture curing polyurethane resin, a light free radical polymerization initiator and a water removing agent.
The present invention will be described in detail below.
The present inventors have found that by adding a water scavenger to a moisture-curable resin composition containing a radical polymerizable compound, a moisture-curable polyurethane resin, and a photo radical polymerization initiator, both storage stability and adhesiveness can be improved, and have completed the present invention.
The light-moisture-curable resin composition of the present invention contains a water scavenger.
The water scavenger is not particularly limited, and examples thereof include physical adsorption-based water scavengers, water scavengers chemically reacting with water, and the like.
As the water scavenger, a compound having at least 1 group selected from an isocyanate group, an isothiocyanate group and a carbodiimide group is preferably used. The compound having at least 1 group selected from the group consisting of an isocyanate group, an isothiocyanate group and a carbodiimide group has high reactivity with moisture, and has an effect of preventing a reaction between moisture and a moisture-curable polyurethane resin during storage. The compound having a urethane bond and an isocyanate group is treated as the moisture-curable polyurethane resin.
In the case where the compound having at least 1 group selected from the group consisting of an isocyanate group, an isothiocyanate group and a carbodiimide group is used as the water scavenger, the compound needs to move in the system and rapidly react with moisture, and therefore, the molecular weight is preferably small, and particularly in the case of the compound having an isocyanate group or an isothiocyanate group, the preferable upper limit of the molecular weight is 500, and more preferably 300. In addition, from the viewpoint of accelerating the reaction rate with moisture and efficiently removing moisture, a compound containing an isocyanate group having an aromatic ring or an isothiocyanate group having an aromatic ring is preferable. The carbodiimide group-containing compound is not particularly limited. Further, the compound having at least 1 group selected from the group consisting of an isocyanate group, an isothiocyanate group and a carbodiimide group, which is not reactive with moisture, contributes to curing of the moisture-curable polyurethane resin, and the crosslinking density is increased, whereby the cured product of the obtained moisture-curable resin composition is excellent in adhesiveness.
In addition, the preferable lower limit of the molecular weight of the compound having at least 1 kind of group selected from the group consisting of an isocyanate group, an isothiocyanate group and a carbodiimide group is 100, and the more preferable lower limit is 150.
Among the compounds having at least 1 group selected from the group consisting of an isocyanate group, an isothiocyanate group and a carbodiimide group, a compound having an isocyanate group is preferable. When a compound having an isocyanate group is used as the water scavenger, the compound may be the same as or different from a polyisocyanate compound which is a raw material of a moisture-curable polyurethane resin described later.
The compound having at least 1 group selected from the group consisting of an isocyanate group, an isothiocyanate group and a carbodiimide group may be monofunctional or polyfunctional, and is preferably 2-functional from the viewpoint of having an appropriate reactivity with moisture.
The compound having at least 1 group selected from the group consisting of an isocyanate group, an isothiocyanate group and a carbodiimide group is a compound which chemically removes moisture, and each material may be physically treated in advance (moisture removal by another water scavenger such as zeolite described later) as necessary before each material used in the moisture-curable resin composition of the present invention is blended.
Among the compounds having at least 1 group selected from the group consisting of an isocyanate group, an isothiocyanate group and a carbodiimide group, specific examples of the compound having an isocyanate group 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 (NDI), 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.
Among the compounds having at least 1 group selected from the group consisting of an isocyanate group, an isothiocyanate group and a carbodiimide group, specific examples of the compound having an isothiocyanate group include benzyl isothiocyanate, phenyl isothiocyanate, 4-phenylbutyl isothiocyanate and 3-phenylpropyl isothiocyanate.
Among the compounds having at least 1 group selected from the group consisting of an isocyanate group, an isothiocyanate group and a carbodiimide group, specific examples of the compound having a carbodiimide group include N, N-dicyclohexylcarbodiimide, N-diisopropylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, bis (2, 6-diisopropylphenyl) carbodiimide and the like, and commercially available products include CARBODILITE LA-1 (manufactured by nippon).
Among these, compounds having an isocyanate group are preferable in terms of an excellent effect of improving the crosslinking density and making the resulting cured product of the moisture-curable resin composition a cured product having excellent adhesiveness. These compounds having at least 1 group selected from the group consisting of an isocyanate group, an isothiocyanate group and a carbodiimide group may be used alone, or 2 or more kinds may be used in combination.
As the water-removing agent, the water-removing agent other than the compound having at least 1 group selected from the group consisting of an isocyanate group, an isothiocyanate group and a carbodiimide group can be used. Examples of the other water-removing agents include metal oxides such as boron oxide, calcium oxide, magnesium oxide, chromium oxide, manganese oxide, iron oxide, copper oxide, silver oxide, indium oxide, barium oxide, lead oxide, phosphorus oxide, strontium oxide, and activated alumina; metal sulfates such as magnesium sulfate, sodium sulfate, and nickel sulfate; metal hydroxides such as sodium hydroxide and potassium hydroxide; a metal hydride; organic metal compounds such as aluminum oxide octoate; zeolite compounds, hydrotalcite compounds, silica gel, alumino silica gel (アルミノシリカゲル), sodium dithionite, anhydrides of mono-or polycarboxylic acids, acrylates, carbohydrazide, ascorbate, gallic acid, alkoxysilanes, carbon nanotubes, activated carbon, cellulose powder, and the like.
These other water scavengers may be used alone or in combination of 2 or more. In addition, these other water scavengers may be used in combination with the above-mentioned compound having at least 1 group selected from the group consisting of an isocyanate group, an isothiocyanate group and a carbodiimide group.
The content of the water scavenger is preferably 0.05 parts by weight in the total 100 parts by weight of the moisture-curable resin composition of the present invention, and 10 parts by weight in the upper limit. If the content of the water scavenger is less than 0.05 parts by weight, the resulting moisture-curable resin composition may have poor storage stability and adhesiveness. If the content of the water scavenger is more than 10 parts by weight, the moisture-curable polyurethane resin may be excessively crosslinked during curing, and may become brittle and hard. The content of the water scavenger is preferably 0.1 part by weight at the lower limit, 5.0 parts by weight at the upper limit, 0.2 parts by weight at the lower limit, 3.0 parts by weight at the upper limit, and 1.5 parts by weight at the upper limit.
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, but a compound having an unsaturated double bond as a radical reactive functional group is preferable, 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; obtaining an epoxy (meth) acrylate by reacting (meth) acrylic acid with an epoxy compound; urethane (meth) acrylates obtained by reacting isocyanates with (meth) acrylic acid derivatives having a hydroxyl group, and the like.
In the present specification, the "(meth) acrylate" means 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, stearyl (meth) acrylate, isobornyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, methoxyethylene glycol (meth) acrylate, 2-ethoxyethyl (meth) acrylate, N-acryloyloxyethylhexahydrophthalimide and the like, and various imide acrylates, Tetrahydrofurfuryl (meth) acrylate, 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, isopropyl (meth) acrylate, n-butyl (meth) acrylate, n-, Isomyristyl (meth) acrylate, 2-butoxyethyl (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, and mixtures thereof, Propylene oxide-added bisphenol a di (meth) acrylate, ethylene oxide-added bisphenol F di (meth) acrylate, dimethylol dicyclopentadienyl 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 and (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-added 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-810NM (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-50TE (manufactured by Nippon Tekken chemical Co., Ltd.).
Examples of commercially available products of the above diphenyl ether type epoxy resins include YSLV-80DE (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 EPICLONEXA-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 EPICLONHP7200 (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.), EPOLLIGHT 80MFA (available from Kyoho chemical Co., Ltd.), DENACOLEX-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 DENACOLEX-147 (manufactured by NagaseChemtex).
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-80XY, YSLV-90CR (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-ALLXLTD), EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020 (both manufactured by Newzhongwa chemical industries), NACCESTER M-600A, EPXY ESTER 40EM, EPXY ESTER 70PA, EPOXER 200PA, EPXY ESTER 80MFA, EPXY ESTER 3002M, EPOXESTER 3002A, EPOXY ESTER1600, EPXY ESTER A, DEXY 3000, DEXY 393000, DEESTER 141, DEESTER 3000, DEESOL 141, DEESTER 3000, DEESOL 3000, and the like.
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, EBECRYL8804, EBECRYL8803, EBECRYL8807, EBECRYL9260, EBECRYL 1290, EBECRYL5129, EBECRYL4842, EBECRYL210, EBECRYL4827, EBECRYL6700, EBECRYL220, EBECRYL2220, KRM7735, KRM-8295 (all manufactured by DAICEL-ALLTRD), AresUN-9000H, Aresjn-9000A, AresRuntryn 7100, AresRsU-6H, U, AresRUN-HA-1200, AresRU-200, AresRYL HA-200, AresRYL 3, AresRU-200, AresRU-A, AresRYL 3, and ARECRYL 3, U-15HA, U-122A, U-122P, U-108, U-108A, U-324A, U-340A, U-340P, U-1084A, U-2061BA, UA-340P, UA-4100, UA-4000, UA-4200, UA-4400, UA-5201P, UA-7100, UA-7200, UA-W2A (all manufactured by Ninghamun chemical industries Co., Ltd.), AI-600, AH-600, AT-600, UA-101I, UA-101T, UA-306H, UA-306I, UA-306T (all manufactured by Kyoho 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-pyrrolidone, 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 adhesiveness. 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 obtained photo-moisture-curable resin composition may have poor adhesiveness. 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 polyurethane resin. In the moisture-curable polyurethane 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 polyurethane resin may contain only 1 isocyanate group or 2 or more isocyanate groups in 1 molecule. Among these, a polyurethane prepolymer having isocyanate groups at both ends is preferable.
The polyurethane 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 and the polyisocyanate compound is usually carried out in a range of [ NCO ]/[ OH ] - [ 2.0 to 2.5 in terms of a molar ratio of a hydroxyl group (OH) in the polyol compound to an isocyanate group (NCO) in the polyisocyanate compound.
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, polyalkylene 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 polyhydric alcohol, and a poly-caprolactone polyol obtained by ring-opening polymerization of 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-opening 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 bisphenol-type polyoxyalkylene modified product is a polyether polyol obtained by addition reaction of an alkylene oxide (for example, ethylene oxide, propylene oxide, butylene oxide, isobutylene oxide, etc.) to an active hydrogen moiety of a bisphenol-type molecular skeleton, 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 1, 6-hexanediol polycarbonate polyol and ethylene cyclohexane 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 polyurethane resin is preferably a polyurethane 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 polyurethane resin having excellent compatibility with the radical polymerizable compound can be obtained.
Among them, polyether polyols containing a ring-opening polymerization compound of propylene glycol, a Tetrahydrofuran (THF) compound, or a ring-opening polymerization compound of a tetrahydrofuran compound having a substituent such as a methyl group are preferably used.
[ solution 1]
Figure BDA0002504110930000131
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.
Note that the case where L is 0 means a case where the carbon bonded to R is directly bonded to oxygen.
Further, the moisture-curable polyurethane resin may have a radical polymerizable functional group.
The radical polymerizable functional group that the moisture-curable polyurethane 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 polyurethane resin having a radical polymerizable functional group is not contained in a radical polymerizable compound, and is treated as a moisture-curable polyurethane resin.
The weight average molecular weight of the moisture-curable polyurethane 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 polyurethane 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 polyurethane resin is more than 1 ten thousand, the resulting light-moisture-curable resin composition may have poor coatability. The weight average molecular weight of the moisture-curable polyurethane resin is 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 obtained by measuring the weight average molecular weight by Gel Permeation Chromatography (GPC) and converting the weight average molecular weight into polystyrene. Examples of the column for measuring the weight average molecular weight in terms of polystyrene by GPC include ShodexLF-804 (manufactured by Showa Denko K.K.). Examples of the solvent used in GPC include tetrahydrofuran.
The content of the moisture-curable polyurethane 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 polyurethane resin. When the content of the moisture-curable polyurethane 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 polyurethane resin is more than 90 parts by weight, the resulting moisture-curable resin composition may have poor photocurability. The content of the moisture-curable polyurethane 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, and thioxanthone.
Examples of commercially available products of the photo radical polymerization initiator include IRGACURE184, IRGACURE369, IRGACURE379, IRGACURE651, IRGACURE784, IRGACURE819, IRGACURE907, IRGACURE2959, IRGACURE OXE01, LucirinTPO (all manufactured by BASF Japan corporation), 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 obtained 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 obtained 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 further contain 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 only 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 an ultraviolet region, particularly 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 having a property of sufficiently shielding light having a wavelength in the visible light region to impart light-shielding properties to the moisture-curable resin composition of the present invention and transmitting 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 a substance capable of initiating a reaction by light having a wavelength (370 to 450nm) at which the transmittance of the titanium black is increased, as a photo-radical polymerization initiator. 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, 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, or the like can 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 display device manufactured using the moisture-curable resin composition of the present invention can have high contrast without light leakage and has 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。
Further, the preferable lower limit of the sheet resistance (シ - ト resistance) of the titanium black is 10 when mixed with a resin (70% blending)9Omega/□, more preferably the lower limit is 1011Ω/□。
The volume resistance of the titanium black is preferably 0.5 Ω · cm at the lower limit, 3 Ω · cm at the upper limit, 1 Ω · cm at the lower limit, and 2.5 Ω · cm at the upper limit.
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, for example, the distance between substrates of the display device is 30nm at the lower limit, and 500nm at the upper limit. If the primary particle size of the light-shading agent is less than 30nm, the viscosity and thixotropy of the resulting moisture-curable resin composition increase remarkably, and the workability is 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 cannot 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 properties 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 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 preferable 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 particleasing 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, and the like. 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 treatment, alkylation treatment, and epoxidation treatment. 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, for example, the following method: a method of 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 water scavenger, and optionally additives, using a mixer such as a homogenizing disperser, a homogenizing mixer, a universal mixer, a planetary mixer, a kneader, or a three-roll mill.
The moisture-curable resin composition of the present invention preferably contains water in an amount of 100ppm or less. When the moisture content is more than 100ppm, the moisture-curable polyurethane resin is likely to react with moisture during storage, and the storage stability of the photo-moisture-curable resin composition is poor. The water content is more preferably 80ppm or less.
The moisture content can be measured by a karl fischer moisture measuring device.
The preferable 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 preferable upper limit is 500 pas. When the viscosity is less than 50 pas or more than 500 pas, workability in applying the resin composition to an adherend such as a substrate is deteriorated when the resin 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, workability when the light/moisture-curable resin composition is used for an adhesive for electronic components or an adhesive for display elements is deteriorated when the composition is applied to an adherend such as a substrate. 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 represents 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 storage stability and adhesiveness.
Drawings
Fig. 1(a) is a schematic view of a sample for adhesiveness evaluation as viewed from above, and fig. 1(b) is a schematic view of a sample for adhesiveness evaluation as viewed from the side.
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 polyurethane 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, under normal pressure, 26.5 parts by weight of Pure MDI (manufactured by Nissan Co., Ltd.) as a diisocyanate was added thereto, and the mixture was stirred at 80 ℃ for 3 hours to react, thereby obtaining a polyurethane prepolymer A (weight-average molecular weight 2700).
Synthesis example 2 (preparation of polyurethane prepolymer B)
100 parts by weight of polypropylene glycol (product of Asahi glass company, "EXCENOL 2020") as a polyol and 0.01 part by weight of dibutyltin dilaurate were put in 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 polyurethane prepolymer B (weight average molecular weight 2900).
Synthesis example 3 (preparation of polyurethane prepolymer C)
Into a reaction vessel containing the polyurethane 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 a polyurethane prepolymer C having an isocyanate group and a methacryloyl group at the molecular terminal (weight-average molecular weight 3100).
(examples 1 to 19, comparative examples 1 and 2)
The materials were stirred by a planetary stirring apparatus (manufactured by Thinky corporation, "ぁわとり 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 19 and comparative examples 1 and 2.
In tables 1 and 2, "polyurethane prepolymer a" is the polyurethane prepolymer having isocyanate groups at both ends described in synthesis example 1, "polyurethane prepolymer B" is the polyurethane prepolymer having isocyanate groups at both ends described in synthesis example 2, and "polyurethane prepolymer C" is the polyurethane 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.
(storage stability)
The moisture-curable resin compositions obtained in examples and comparative examples were measured for viscosity at 25 ℃ for 1 week and initial viscosity immediately after production, and the value represented by (viscosity at 25 ℃ after 1 week of storage)/(initial viscosity) at that time was taken as the viscosity change rate, and the storage stability was evaluated by determining the viscosity change rate as "o" for samples having a viscosity change rate of less than 1.1, as "Δ" for samples having a viscosity of 1.1 to less than 1.5, and as "x" for samples having a viscosity of 1.5 or more.
The viscosity was measured using a cone-plate viscometer ("VISCOMETERTV V-22" manufactured by Toyobo industries Co., Ltd.) at 25 ℃ and a rotation speed of 1 rpm.
(amount of moisture)
The moisture-curable resin compositions obtained in examples and comparative examples were dissolved in a dehydrating solvent, and the moisture content was measured by a Karl Fischer moisture meter (MKC-610, manufactured by Kyoto electronics industries, Ltd.).
(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 a polycarbonate substrate and left overnight, thereby moisture-curing the glass plate to obtain 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 side surface (fig. 1 (b)).
The prepared sample for evaluation of adhesiveness was subjected to tensile test at a rate of 5mm/sec in the shear direction using a tensile tester, and the strength at the time of peeling of the substrate was measured.
(tackiness)
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 moisture-curable resin composition was photocured to prepare a sample for evaluation of tackiness. The adhesion strength of the obtained sample for evaluation of adhesion was measured using an adhesion tester (TAC-100, manufactured by RHESCA corporation).
[ Table 1]
Figure BDA0002504110930000221
[ Table 2]
Figure BDA0002504110930000231
Industrial applicability
The present invention can provide a light/moisture-curable resin composition having excellent storage stability and adhesiveness. Further, according to the present invention, an adhesive for electronic components and an adhesive for display elements, which are produced by using the light/moisture curable resin composition, can be provided.
Description of the symbols
1. Polycarbonate resin substrate
2. Light-moisture-curable resin composition
3. Glass plate

Claims (12)

1. An adhesive for electronic parts, which is characterized by being obtained by using a light-moisture-curable resin composition,
the photo-moisture-curable resin composition contains a radical polymerizable compound, a moisture-curable polyurethane resin, a photo-radical polymerization initiator, and a water scavenger, and the water scavenger contains a compound having an isocyanate group containing an aromatic ring and being a 2-functional group,
the moisture-curable resin composition contains the water scavenger in an amount of 0.05 to 10 parts by weight based on 100 parts by weight of the entire composition.
2. The adhesive for electronic components according to claim 1, wherein the compound having an aromatic ring-containing isocyanate group and being 2-functional comprises at least 1 selected from tolidine diisocyanate, toluene diisocyanate, diphenylmethane diisocyanate, and naphthalene diisocyanate.
3. The adhesive for electronic components according to claim 1, wherein the amount of water contained is 100ppm or less.
4. 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.
5. The adhesive for electronic parts according to claim 1, comprising an opacifier.
6. The adhesive for electronic parts according to claim 1, comprising a filler having a primary particle diameter of 1 to 50 nm.
7. An adhesive for display elements, which is obtained by using a light-moisture-curable resin composition,
the photo-moisture-curable resin composition contains a radical polymerizable compound, a moisture-curable polyurethane resin, a photo-radical polymerization initiator, and a water scavenger, and the water scavenger contains a compound having an isocyanate group containing an aromatic ring and being a 2-functional group,
the moisture-curable resin composition contains the water scavenger in an amount of 0.05 to 10 parts by weight based on 100 parts by weight of the entire composition.
8. The adhesive according to claim 7, wherein the compound having an aromatic ring-containing isocyanate group and being 2-functional comprises at least 1 selected from tolidine diisocyanate, toluene diisocyanate, diphenylmethane diisocyanate, and naphthalene diisocyanate.
9. The adhesive for display elements according to claim 7, wherein the amount of water contained is 100ppm or less.
10. The adhesive for display elements according to claim 7, wherein the radical polymerizable compound comprises a monofunctional radical polymerizable compound and a polyfunctional radical polymerizable compound.
11. The adhesive for display elements according to claim 7, which contains an opacifier.
12. The adhesive for display elements according to claim 7, wherein the filler has a primary particle diameter of 1 to 50 nm.
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