CN114423834A - Light-moisture-curable resin composition, adhesive for electronic component, method for producing electronic component, and cured body - Google Patents
Light-moisture-curable resin composition, adhesive for electronic component, method for producing electronic component, and cured body Download PDFInfo
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- CN114423834A CN114423834A CN202180005424.5A CN202180005424A CN114423834A CN 114423834 A CN114423834 A CN 114423834A CN 202180005424 A CN202180005424 A CN 202180005424A CN 114423834 A CN114423834 A CN 114423834A
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- moisture
- resin composition
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- curable resin
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- 238000003860 storage Methods 0.000 claims description 28
- 125000006850 spacer group Chemical group 0.000 claims description 22
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- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
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- UDXXYUDJOHIIDZ-UHFFFAOYSA-N 2-phosphonooxyethyl prop-2-enoate Chemical compound OP(O)(=O)OCCOC(=O)C=C UDXXYUDJOHIIDZ-UHFFFAOYSA-N 0.000 description 2
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- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- AMJYHMCHKZQLAY-UHFFFAOYSA-N tris(2-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound O=C=NC1=CC=CC=C1OP(=S)(OC=1C(=CC=CC=1)N=C=O)OC1=CC=CC=C1N=C=O AMJYHMCHKZQLAY-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229940042596 viscoat Drugs 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Images
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
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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
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- 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
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
-
- 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
- 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
- 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
- C08F290/067—Polyurethanes; Polyureas
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- 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
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- 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
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- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
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- 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
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- 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
- C09J11/04—Non-macromolecular additives inorganic
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- 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
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- 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
- C09J11/08—Macromolecular additives
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- 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
- C09J175/06—Polyurethanes from polyesters
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- 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
- C09J175/08—Polyurethanes from polyethers
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- 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
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- 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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
Abstract
The light-moisture-curable resin composition of the present invention comprises a radical polymerizable compound, a moisture-curable polyurethane resin and a photopolymerization initiator, wherein the moisture-curable polyurethane resin comprises a polymer having a polyester skeletonMoisture-curable polyurethane resin obtained by irradiating 1000mJ/cm2The cured product in a state of being photocured by ultraviolet rays has a thickness change rate of 50% or less before and after application of a load of 0.04 MPa.
Description
Technical Field
The present invention relates to a light-moisture-curable resin composition, an adhesive for electronic components, a method for producing an electronic component using the adhesive for electronic components, and a cured product of 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 thin thickness, light weight, and low power consumption. In these display elements, sealing of a liquid crystal or a light emitting layer, adhesion of various members such as a substrate, an optical film, and a protective film, and the like are generally performed using a photocurable resin composition.
However, in the modern times in which various mobile devices with display elements such as mobile phones and portable game machines have been widely used, the miniaturization of the display elements is the most important 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 cannot be 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 coated on the portion which cannot be reached by light is insufficiently cured. Therefore, there has been also performed an operation of using a photo-thermal curable resin composition as a resin composition which can be sufficiently cured even when applied to a portion which cannot be reached by light, and using both photo-curing and thermal curing, but there is a possibility that heating at a high temperature may adversely affect an element or the like.
In recent years, electronic components such as semiconductor chips are required to be highly integrated and downsized, and for example, a plurality of thin semiconductor chips are bonded via an adhesive layer to form a stacked body of semiconductor chips. Such a stacked body of semiconductor chips is manufactured, for example, by the following method: after coating an adhesive on one semiconductor chip, laminating another semiconductor chip via the adhesive, and then curing the adhesive; an adhesive is filled between the semiconductor chips held at a fixed interval, and then the adhesive is cured. Similarly, in the narrow-edge design, a method of semi-curing the applied adhesive and then completely curing it has been studied. Therefore, the use of a photo-moisture curable resin composition as an adhesive has been studied for laminating small semiconductor chips and bonding electronic parts such as display elements designed with narrow edges.
For example, patent document 1 discloses a light-moisture curable resin composition and an adhesive for electronic components, in which the cured product has excellent flexibility and reliability in a high-temperature and high-humidity environment.
Documents of the prior art
Patent document
Patent document 1: international publication No. 2016/076407
Disclosure of Invention
Problems to be solved by the invention
However, in the bonding of small electronic parts or in the design of narrow edges, not only the bonding strength but also the durability of the bonding force are sometimes required.
Specifically, electronic components such as semiconductor chips and display elements are sometimes exposed to a high temperature of about 80 ℃ in an assembly process, a use time, and the like of the electronic components due to external heating or heat generation of the electronic components themselves during operation. In addition, the electronic component may be exposed to a low temperature of 0 ℃ or lower depending on the use environment. On the other hand, when different materials are bonded to each other by an adhesive, the different materials have different thermal expansion coefficients from each other, and therefore, if a temperature change occurs as described above, the adhesive may generate a large strain during an assembly process or during use. When such strain is repeatedly generated, the adhesive is locally broken, and the adhesive strength of the adhesive is reduced. Therefore, there is a demand for suppressing the decrease in the adhesive strength by stress relaxation even after the repeated generation of strain, and for improving the durability of the adhesive strength.
Further, in recent years, even when electronic components such as semiconductor chips and display elements are exposed to high temperatures by external heating or heat generation of the electronic components themselves during operation, sufficient adhesive force for firmly bonding the electronic components is required.
The photo-moisture curable resin composition disclosed in patent document 1 has excellent stress relaxation properties and durability of adhesive force because a cured product having appropriate flexibility can be obtained. However, the photo-moisture curable resin composition disclosed in patent document 1 has a problem of insufficient adhesive strength at high temperatures.
Accordingly, an object of the present invention is to provide a light-moisture curable resin composition and an adhesive for electronic components, which are excellent in both durability of adhesive force and sufficient adhesive force at high temperatures.
Means for solving the problems
As a result of intensive studies, the present inventors have made studies on moisture-curable urethane resins in order to improve the high-temperature adhesive strength of conventional light-moisture-curable resin compositions. The present inventors have also found that the high-temperature adhesive strength can be greatly improved by blending a moisture-curable urethane resin having a polyester skeleton as the moisture-curable urethane resin.
On the other hand, the present inventors have found a problem that sufficient durability of adhesive force cannot be obtained when a moisture-curable urethane resin having a polyester skeleton is used as the moisture-curable urethane resin.
As a result of intensive studies, the present inventors have found that a high level of both high-temperature adhesive strength and durability of adhesive strength can be achieved by setting the thickness change rate before and after applying a load to a cured product in a photocured state to 50% or less, and have completed the present invention.
Namely, the present invention provides the following [1] to [30 ].
[1] A photo-moisture curable resin composition comprising a radical polymerizable compound, a moisture curable polyurethane resin and a photopolymerization initiator,
the moisture-curable polyurethane resin comprises a moisture-curable polyurethane resin having a polyester skeleton,
for the light passing through 1000mJ/cm2The cured product in a state of being photocured by ultraviolet rays of (1) has a thickness change rate of 50% or less before and after application of a load of 0.04 MPa.
[2] The photo-moisture-curable resin composition according to the above [1], which has a viscosity of 3000 pas or less at 25 ℃ and 1 rpm.
[3] The photocurable resin composition according to [1] or [2], wherein the moisture-curable polyurethane resin further comprises a moisture-curable polyurethane resin having a polyether skeleton.
[4] The photo-moisture-curable resin composition according to [3], wherein the moisture-curable polyurethane resin having a polyether skeleton is obtained by reacting a polyether polyol having 2 or more hydroxyl groups in 1 molecule with a polyisocyanate compound having 2 or more isocyanate groups in 1 molecule.
[5] The photo-moisture curable resin composition according to [4], wherein the polyether polyol has a structure represented by the following formula (1).
In the formula (1), R represents any one of a hydrogen atom, a methyl group and an ethyl group, l is an integer of 0 to 5, m is an integer of 1 to 500, and n is an integer of 1 to 10.
[6] The photo-moisture-curable resin composition according to [4], wherein the polyether polyol is at least 1 selected from the group consisting of polypropylene glycol, a ring-opened polymer of a tetrahydrofuran compound, and a ring-opened polymer of a tetrahydrofuran compound having a methyl group as a substituent.
[7] The photo-moisture-curable resin composition according to [4], wherein the polyether polyol is polypropylene glycol.
[8] The photocurable resin composition according to [1] or [2], wherein the moisture-curable polyurethane resin having a polyester skeleton has a polyether skeleton in a molecule.
[9] The photo-moisture-curable resin composition according to any one of the above [1] to [8], further comprising spacer particles.
[10] The moisture-curable resin composition according to any one of [1] to [9], wherein a content of the radical polymerizable compound is 3% by mass or more in 100% by mass of the moisture-curable resin composition.
[11] The photo-moisture-curable resin composition according to any one of [1] to [10], wherein the photopolymerization initiator is a compound having an acylphosphine oxide skeleton or a compound having an α -aminoalkylbenzophenone skeleton.
[12] The photo-moisture-curable resin composition according to any one of the above [1] to [11], wherein the cured product in a photo-cured state has a storage modulus at 25 ℃ of 10kPa or more.
[13] The photocurable resin composition according to any one of the above [1] to [12], wherein a cured product obtained by allowing the cured product in a photocured state to stand in an environment of 23 ℃ and 50 RH% for 3 days has a storage modulus at 25 ℃ of 1MPa or more.
[14] The photo-moisture-curable resin composition according to any one of the above [1] to [13], wherein the moisture-curable polyurethane resin having a polyester skeleton is obtained by reacting a polyester polyol having 2 or more hydroxyl groups in 1 molecule with a polyisocyanate compound having 2 or more isocyanate groups in 1 molecule.
[15] The photo-moisture-curable resin composition according to [14], wherein the polyester polyol is an ester of at least 1 polycarboxylic acid selected from the group consisting of phthalic acid, terephthalic acid, isophthalic acid and adipic acid, and at least 1 polyol selected from the group consisting of 1, 6-hexanediol and 1, 4-butanediol.
[16] The photo-moisture-curable resin composition according to any one of [1] to [15], wherein the radical polymerizable compound comprises a (meth) acrylic compound.
[17] The photo-moisture-curable resin composition according to [16], wherein the (meth) acrylic compound comprises a monofunctional (meth) acrylic compound.
[18] The photo-moisture-curable resin composition according to [17], wherein the (meth) acrylic compound further comprises a polyfunctional (meth) acrylic compound.
[19] The photo-moisture-curable resin composition according to [18], wherein the content of the polyfunctional (meth) acrylic compound is 1% by mass or more and 50% by mass or less with respect to the total amount of the radical polymerizable compounds.
[20] The photo-moisture-curable resin composition according to at least any one of [17] to [19], wherein the monofunctional (meth) acrylic compound is a (meth) acrylate compound.
[21] The photo-moisture-curable resin composition according to any one of [1] to [20], wherein the content of the radical polymerizable compound is 50% by mass or less in 100% by mass of the photo-moisture-curable resin composition.
[22] The photo-moisture-curable resin composition according to any one of [1] to [21], wherein the moisture-curable polyurethane resin is contained in an amount of 45 mass% to 95 mass% in 100 mass% of the photo-moisture-curable resin composition.
[23] The photo-moisture-curable resin composition according to any one of [1] to [22], wherein the content of the moisture-curable polyurethane resin having a polyester skeleton is 25% by mass or more and 95% by mass or less in 100% by mass of the photo-moisture-curable resin composition.
[24] The moisture-curable resin composition according to any one of [1] to [23], wherein the content of the photopolymerization initiator in the moisture-curable resin composition is 0.01 to 10 parts by mass, based on 100 parts by mass of the total amount of the radical polymerizable compound and the moisture-curable polyurethane resin.
[25] The photo-moisture-curable resin composition according to any one of [1] to [24], wherein the thickness change rate is 5% or more.
[26] An adhesive for electronic parts, which comprises the photo-moisture-curable resin composition according to any one of [1] to [25 ].
[27] A method of manufacturing an electronic device, comprising:
a step of heating the adhesive for electronic components according to [26 ];
and applying the adhesive for electronic components to the electronic components.
[28] A method for bonding electronic parts to each other or bonding electronic parts to other parts by using the adhesive for electronic parts as recited in [26 ].
[29] A cured product of the photo-moisture-curable resin composition according to any one of [1] to [25 ].
[30] An electronic device comprising the cured product according to [29 ].
Effects of the invention
The present invention can provide a photo-moisture curable resin composition and an adhesive for electronic components, which are excellent in both durability of adhesive strength and sufficient adhesive strength at high temperatures.
Drawings
Fig. 1 is a schematic diagram showing a method of adhesion test, fig. 1(a) is a plan view, and fig. 1(b) is a side view.
Detailed Description
The present invention will be described in detail below.
[ light-moisture-curable resin composition ]
The photo-moisture-curable resin composition of the present invention comprisesA radical polymerizable compound, a moisture-curable polyurethane resin and a photopolymerization initiator, which are irradiated at 1000mJ/cm2The cured product in a state of being photocured by ultraviolet rays of (1) has a thickness change rate of 50% or less before and after application of a load of 0.04 MPa.
In the photo-moisture-curable resin composition of the present invention, the moisture-curable polyurethane resin contains a moisture-curable polyurethane resin having a polyester skeleton. The light-moisture-curable resin composition of the present invention can improve the adhesive strength in a high-temperature environment by containing an amine ester prepolymer having a polyester skeleton.
In addition, the light-moisture-curable resin composition of the present invention has good stress relaxation properties and can improve the durability of the adhesive force by setting the thickness change rate before and after applying a load to a cured product in a light-cured state to 50% or less, and can maintain a constant adhesive force even when repeatedly placed in, for example, a high-temperature environment or a low-temperature environment. The thickness change rate before and after the application of the load is preferably 45% or less, and more preferably 40% or less. In addition, the thickness change rate is preferably 5% or more, more preferably 10% or more, from the viewpoint of easily improving the adhesive strength at high temperatures.
(thickness Change ratio of cured product in light-cured State)
The cured product in a photocured state is a cured product in a state in which the photocurable resin composition is photocured without being moisture-cured. The thickness change rate before and after applying a load to a cured product in a photocured state can be measured as follows.
< rate of change in thickness of cured product in photocured State >
The photo-moisture curable resin composition was coated on a polycarbonate substrate (length 50mm, width 25mm, thickness 2mm) so that the line width was 1.0. + -. 0.1mm, the length was 25. + -. 0.2mm, and the thickness was 0.4. + -. 0.1mm using a dispenser. Within 1 minute after the completion of the coating, 1000mJ/cm was irradiated by using a UV-LED lamp2The ultraviolet ray of (3) causes the photo-moisture curable resin composition to be photo-cured. Further, the wavelength of the UV-LED lamp may be appropriately selected depending on the absorption wavelength of the photopolymerization initiator contained, for exampleFor example, a lamp having a wavelength of 365nm may be used. Immediately after the irradiation of ultraviolet rays, a glass substrate having the same size as a polycarbonate substrate was stacked on the cured product in a photocured state in an environment of 25 ℃, and a 100g weight was left standing thereon for 10 seconds, whereby a load of 0.04MPa was applied to the entire cured product in a photocured state for 10 seconds. Immediately after the light irradiation and after the application of the load, the thickness of the central portion of the cured product in the light-cured state was measured using a digital microscope, and the thickness change rate (%) was measured as follows.
Thickness change rate (%) (thickness immediately after light irradiation-thickness after load application)/(thickness immediately after light irradiation) × 100
(storage modulus of cured product in light-cured State)
The storage modulus of a cured product of the photocurable resin composition of the present invention in a photocured state at 25 ℃ is, for example, 2kPa or more, preferably 10kPa or more, more preferably 15kPa or more, and still more preferably 20kPa or more. By setting the storage modulus at 25 ℃ of the cured product in a photocured state to the lower limit or more, the thickness change rate of the cured product in the photocured state can be easily adjusted within a predetermined range.
From the viewpoint of improving the initial adhesion, the upper limit of the storage modulus at 25 ℃ of the cured product in a photocured state is preferably 200kPa or less, and more preferably 100kPa or less.
The storage modulus at 25 ℃ of a cured product in a photocured state can be measured as follows.
< storage modulus in photocured State >
3g of the photo-moisture curable resin composition was placed in a UV irradiation rheometer (trade name HAAKE MARS 40/60, manufactured by Thermo Fisher Scientific Co., Ltd.). 30 seconds after the completion of the standing, 1000mJ/cm was irradiated by using a UV-LED lamp2Ultraviolet rays of (2) to cure it. After 60 seconds of irradiation with ultraviolet light, the shear storage modulus was measured at a frequency F of 1.6Hz in an environment of 25 ℃ and 50 RH%. Further, the wavelength of the UV-LED lamp may be appropriate depending on the absorption wavelength of the photopolymerization initiator containedAlternatively, for example, a lamp having a wavelength of 365nm may be used.
(storage modulus of cured product in light-moisture-cured State)
The storage modulus of a cured product obtained by photo-moisture curing of the photo-moisture curable resin composition of the present invention at 25 ℃ is preferably 1MPa or more, more preferably 5MPa or more, and still more preferably 10MPa or more. When the storage modulus at 25 ℃ of a cured product in a photo-moisture-cured state is not less than the above lower limit, the high-temperature adhesive strength can be further improved.
In addition, from the viewpoint of improving the durability of the adhesive strength, the storage modulus at 25 ℃ of the cured product in a photo-moisture-cured state is, for example, 700MPa or less, preferably 100MPa or less, and more preferably 70MPa or less.
The storage modulus at 25 ℃ of a cured product in a light-moisture cured state can be measured in the following order.
< storage modulus in light-moisture cured State >
The photo-moisture-curable resin composition was filled in a Teflon (registered trademark) mold having a width of 3mm, a length of 30mm and a thickness of 1 mm. Within 1 minute after completion of filling, 1000mJ/cm was irradiated by using a UV-LED lamp2The ultraviolet ray of (3) causes the curable resin composition to be photocured. The wavelength of the UV-LED lamp may be appropriately selected according to the absorption wavelength of the photopolymerization initiator to be contained, and for example, a lamp having a wavelength of 365nm may be used. Then, the mixture was allowed to stand at 23 ℃ and 50 RH% for 3 days.
The cured product in a photo-moisture cured state was taken out of the mold, and the dynamic viscoelasticity was measured at-100 ℃ to 150 ℃ by a dynamic viscoelasticity measuring apparatus (product of IT measurement and control Co., Ltd., product name "DVA-200"), to determine the storage modulus at room temperature (25 ℃). The measurement conditions were that the deformation mode was tensile, the strain was set to 1%, the measurement frequency was 1Hz, and the temperature rise rate was 5 ℃/min.
(viscosity)
The light-moisture-curable resin composition of the present invention has a viscosity of preferably 3000 pas or less, more preferably 2500 pas or less, even more preferably 2000 pas or less, even more preferably 1500 pas or less, and even more preferably 800 pas or less, as measured with a cone-plate viscometer at 25 ℃ and 1 rpm. When the viscosity at 25 ℃ is not more than the above upper limit, the coating can be performed at normal temperature or at relatively low temperature, and thus the workability in coating is improved. The lower limit of the viscosity is preferably 50Pa · s or more from the viewpoint of suppressing excessive wet spreading at the time of coating.
As described in detail below, the thickness change rate, storage modulus, and viscosity can be adjusted by appropriately changing the radical polymerizable compound, the types and amounts of the components used in the moisture-curable urethane resin, the types and amounts of the components added to the photo-moisture-curable resin composition, and the like.
[ radically polymerizable Compound ]
The light-moisture-curable resin composition of the present invention contains a radical polymerizable compound. The photocurable resin composition of the present invention contains a radical polymerizable compound, and thus has photocurability.
((meth) acrylic acid-based Compound)
The light-moisture-curable resin composition of the present invention preferably contains a compound having a (meth) acryloyl group (hereinafter, described as a "(meth) acrylic compound") as a radical polymerizable compound.
In the present specification, "(meth) acryloyl group" means an acryloyl group or a methacryloyl group, "(meth) acrylic group" means an acrylic group or a methacrylic group, and other similar terms are also used.
Examples of the (meth) acrylic compound include: (meth) acrylate compounds, epoxy (meth) acrylates, urethane (meth) acrylates, polyester (meth) acrylates, and the like. The (meth) acrylic compound may be a monofunctional compound or a polyfunctional compound. Further, the urethane (meth) acrylate has no residual isocyanate group.
Examples of the monofunctional compound in the (meth) acrylate compound include: alkyl (meth) acrylates such as methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isononyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, isomyristyl (meth) acrylate, and stearyl (meth) acrylate; (meth) acrylic esters having an alicyclic structure such as cyclohexyl (meth) acrylate, 4-t-butylcyclohexyl (meth) acrylate, 3, 5-trimethylcyclohexyl (meth) acrylate, isobornyl (meth) acrylate, and dicyclopentenyl (meth) acrylate; hydroxyalkyl (meth) acrylates such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate; alkoxyalkyl (meth) acrylates such as 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, and 2-butoxyethyl (meth) acrylate; alkoxy ethylene glycol (meth) acrylates such as methoxy ethylene glycol (meth) acrylate and ethoxy ethylene glycol (meth) acrylate; polyoxyethylene (meth) acrylates such as methoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, ethylcarbitol (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, ethoxytriethylene glycol (meth) acrylate, and ethoxypolyethylene glycol (meth) acrylate.
The (meth) acrylate compound may have an aromatic ring, and examples thereof include: phenylalkyl (meth) acrylates such as benzyl (meth) acrylate and 2-phenylethyl (meth) acrylate; and phenoxyalkyl (meth) acrylates such as phenoxyethyl (meth) acrylate. Further, (meth) acrylates having a plurality of benzene rings such as a fluorene skeleton and a biphenyl skeleton may be used, and specific examples thereof include: fluorene type (meth) acrylates, ethoxylated o-phenylphenol acrylates, and the like.
In addition, there may be mentioned: phenoxy polyoxyethylene (meth) acrylates such as phenoxy diethylene glycol (meth) acrylate, phenoxy polyethylene glycol (meth) acrylate, nonylphenoxy diethylene glycol (meth) acrylate, and nonylphenoxy polyethylene glycol (meth) acrylate.
Further, as the monofunctional (meth) acrylate compound, there may be mentioned: (meth) acrylates having a heterocyclic structure such as tetrahydrofurfuryl (meth) acrylate, alkoxylated tetrahydrofurfuryl (meth) acrylate, cyclic trimethylolpropane formal (meth) acrylate, and 3-ethyl-3-oxetanylmethyl (meth) acrylate; phthalimide acrylates such as N-acryloyloxyethyl hexahydrophthalimide; various imide (meth) acrylates, 2,2, 2-trifluoroethyl (meth) acrylates, 2,2,3, 3-tetrafluoropropyl (meth) acrylates, 1H, 5H-octafluoropentyl (meth) acrylates, dimethylaminoethyl (meth) acrylates, diethylaminoethyl (meth) acrylates, 2- (meth) acryloyloxyethyl succinate, 2- (meth) acryloyloxyethyl hexahydrophthalate, 2- (meth) acryloyloxyethyl-2-hydroxypropyl phthalate, glycidyl (meth) acrylates, 2- (meth) acryloyloxyethyl phosphate and the like.
Examples of the 2-functional compound in the (meth) acrylate compound include: 1, 3-butanediol di (meth) acrylate, 1, 4-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, dimethylol tricyclodecane di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, and mixtures thereof, Ethylene oxide-added bisphenol a di (meth) acrylate, propylene oxide-added bisphenol a di (meth) acrylate, ethylene oxide-added bisphenol F di (meth) acrylate, dimethylol dicyclopentadiene 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 (meth) acrylate compound include: trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, glycerol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, ethylene oxide-added trimethylolpropane tri (meth) acrylate, propylene oxide-added trimethylolpropane tri (meth) acrylate, caprolactone-modified trimethylolpropane tri (meth) acrylate, ethylene oxide-added isocyanuric acid tri (meth) acrylate, propylene oxide-added glycerol tri (meth) acrylate, tri (meth) acryloyloxyethyl phosphate, di-trimethylolpropane tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and the like.
Examples of the epoxy (meth) acrylate include compounds obtained by reacting an epoxy compound with (meth) acrylic acid. Here, the reaction of the epoxy compound with (meth) acrylic acid may be carried out in the presence of a basic catalyst or the like according to a conventional method. The epoxy (meth) acrylate may be a monofunctional compound or a polyfunctional compound such as a 2-functional compound, but is preferably a polyfunctional compound.
Examples of the epoxy compound to be used as a raw material for synthesizing the epoxy (meth) acrylate include: bisphenol a type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, 2' -diallylbisphenol a type epoxy resin, hydrogenated bisphenol type epoxy resin, propylene oxide adduct bisphenol a type epoxy resin, resorcinol type epoxy resin, biphenyl type epoxy resin, thioether type epoxy resin, diphenyl ether type epoxy resin, dicyclopentadiene type epoxy resin, naphthalene type epoxy resin, phenol novolac type epoxy resin, o-cresol novolac type epoxy resin, dicyclopentadiene novolac type epoxy resin, biphenol novolac type epoxy resin, naphthol novolac type epoxy resin, epoxy acrylamide type epoxy resin, alkyl polyhydric alcohol type epoxy resin, rubber modified type epoxy resin, glycidyl ester compound, bisphenol a type sulfur resin, and the like.
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 (all manufactured by DAICEL-ALLNEX), EA-1010, EA-1020, EA-5323, EA-5520, EACHD, EMA-1020 (all manufactured by Mikanura chemical Co., Ltd.), XYESTER M-600 EM 40, EPOXYESTER 70PA, EPOXYESTER 200PA, EPOXYESTER 80MFA, EPOXYESTER 3002M, EPOXYESTER 3002 3873873875 3893000 EA 3000 EA 39XYSTER 400, EPOXYESTER 1600 (all manufactured by NAC corporation), DEYEOL ACRYLATE DA-141, DEYEOL 67314, DEECRYL ACRYLATE DA, and the like.
The urethane (meth) acrylate can be obtained by, for example, reacting a (meth) acrylic acid derivative having a hydroxyl group with an isocyanate compound. Here, in the reaction of the isocyanate compound and the (meth) acrylic acid derivative, a catalytic amount of a tin-based compound or the like may be used as a catalyst. The urethane (meth) acrylate may be a monofunctional compound or a polyfunctional compound such as a 2-functional compound, and preferably a 2-functional compound.
Examples of the isocyanate compound for obtaining a urethane (meth) acrylate include: polyisocyanate compounds such as isophorone diisocyanate, 2, 4-toluene diisocyanate, 2, 6-toluene diisocyanate, hexamethylene diisocyanate, trimethyl hexamethylene diisocyanate, diphenylmethane-4, 4' -diisocyanate (MDI), hydrogenated MDI, polymeric MDI, 1, 5-naphthalene diisocyanate, norbornane diisocyanate, triazine diisocyanate, Xylylene Diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris (isocyanatophenyl) thiophosphate, tetramethylxylylene diisocyanate, and 1,6, 11-undecane triisocyanate.
Further, as the isocyanate compound, a polyisocyanate compound having a chain extended, which is obtained by a reaction of a polyol with an excess amount of the isocyanate compound, may also be used. Examples of the polyhydric alcohol include: ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate diol, polyether diol, polyester diol, polycaprolactone diol, and the like.
Examples of the (meth) acrylic acid derivative having a hydroxyl group include: mono (meth) acrylates of glycols such as ethylene glycol, 1, 2-propylene glycol, 1, 3-butylene glycol, 1, 4-butylene glycol, and polyethylene glycol; or mono (meth) acrylate or di (meth) acrylate of trihydric alcohols such as trimethylolethane, trimethylolpropane and glycerol; and epoxy (meth) acrylates such as bisphenol a epoxy (meth) acrylates.
Examples of commercially available products of the urethane (meth) acrylate include: m-1100, M-1200, M-1210, M-1600 (all manufactured by Toyo Synthesis Co., Ltd.), EBECRYL230, EBECRYL270, EBECRYL8402, EBECRYL8411, EBECRYL8412, EBECRYL8413, EBECRYL8804, EBECRYL8803, EBECRYL8807, EBECRYL9270, EBECRYL210, EBECRYL4827, EBECRYL6700, EBECRYL220, EBECRYL2220 (all manufactured by DAICEL-ALLNEX Co., Ltd.), ARTIN UN-9000H, ARTRESIN UN-9000A, ARTRESIN UN-7100, ARTIN UN-1255, ARTIN UN-330, ARTIN RESIN UN-3320HB, ARTRESUN-1200K, ARTRESIN SH-500B (all manufactured by Youngsha), HA 2-2, HA-3-3982, HA-2-3982, HA-5932, HA-3982, HA 466-3982, HA-5932, HA-3982, HA 4652, HA 2, HA 3, HA-3976, HA-3970, HA 3, HA 2, HA 3, HA-3970, HA 3, HA-4, HA 3, HA-4, HA 3, HA-4, HA-4, HA 3, HA-4, HA-4, HA-4, and HA-4, HA-4, HA-4, HA-4, HA-460, HA-3, and HA-4, and HA 3, HA-4, and HA including No. K, 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 of which are produced by Mizhongcun chemical industries), AI-600, AH-600, AT-600, UA-101I, UA-101T, UA-306H, UA-306I, UA-306T (all of which are produced by Kyowa chemical Co., Ltd.), CN-902, CN-973, CN-9021, CN-9782 and CN-9833 (all of which are produced by ARKEMA).
Examples of the polyester (meth) acrylate include products obtained by reacting a polyester polyol with (meth) acrylic acid. Examples of commercially available products of the above polyester (meth) acrylate include: ARONIX M-6100, M-6200, M-6250, M-6500, M-7100, M-7300K, M-8030, M-8060, M-8100, M-8530, M-8560, M-9050 (all of which are manufactured by Toyo Synthesis Chemical Co., Ltd.), Doubleimer 2015, Doubleimer 2231-TF, Doubleimer 2319, Doubleimer 257, Doubleimer 276, Doubleimer 284, Doubleimer 2019, Doubleimer 2232, Doubleimer 236, Doubleimer 270, Doubleimer 278, Doubleimer 285, Doubleimer 220, Doubleimer 2315-100, Doubleimer 245, Doubleimer 272, Doubleimer 278X25, Doubleimer 286, Doubleimer 2230-TF, Doubleimer 35, Doubleimer 281, Doubleimer 287 (manufactured by Doubleimer corporation, Doubleimer) 287 and the like.
(Polymer (meth) acrylate)
The photo-moisture curable resin composition may contain, as the (meth) acrylate compound, (meth) acrylate having a number average molecular weight of 5000 or more (hereinafter referred to as "high molecular (meth) acrylate"). When the photo-moisture-curable resin composition contains a high-molecular (meth) acrylate, the thickness change rate can be easily adjusted to a predetermined range. The high-molecular (meth) acrylate is, for example, a polymer having a (meth) acrylate compound as a polymer chain portion and having a (meth) acryloyl group at a terminal. As the (meth) acrylate compound, the above-mentioned compounds can be used, and alkyl (meth) acrylates are preferably used. Examples of such a high-molecular (meth) acrylate include: AA-6 (number average molecular weight 6000, available from Toyo Boseki Kaisha), AB-6 (number average molecular weight 6000, available from Toyo Boseki Kaisha), etc. The upper limit of the number average molecular weight of the polymer (meth) acrylate is not particularly limited, and is, for example, 10 ten thousand or less.
(other radical polymerizable Compound)
As the radical polymerizable compound, other radical polymerizable compounds than the above may 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; vinyl compounds such as styrene, α -methylstyrene, N-vinyl-2-pyrrolidone, and N-vinyl-e-caprolactam.
In the present invention, the thickness change rate of the cured product in the photocured state may be within a predetermined range by appropriately combining the types and contents of the radical polymerizable compounds.
For example, by using a compound having an acryloyl group as the (meth) acrylic compound, the reactivity during light irradiation can be easily improved, and the thickness change rate of a cured product in a light-cured state can be easily adjusted to be within a predetermined range.
Further, for example, by using a polyfunctional (meth) acrylic compound as the (meth) acrylic compound, the reactivity at the time of light irradiation is easily improved, and as a result, the thickness change rate of the cured product in a light-cured state is easily adjusted to be within a predetermined range.
The polyfunctional (meth) acrylic compound may be any compound as long as the above-mentioned compound is appropriately used, and preferably includes a polyfunctional (meth) acrylic compound having a molecular weight of 600 or less (hereinafter, the "polyfunctional (meth) acrylic compound X" will be described).
Examples of the polyfunctional (meth) acrylic compound X include polyfunctional (meth) acrylates having about 6 to 30 carbon atoms, preferably 8 to 20 carbon atoms. The polyfunctional (meth) acrylate compound X is preferably 2 to 4 functional groups, more preferably 2 to 3 functional groups. When the polyfunctional (meth) acrylic compound X is used, the cohesive force (crosslinking density) of the radical polymerizable compound becomes high after photocuring, and the thickness change rate can be further reduced. In addition, the viscosity of the photo-moisture curable resin composition before light irradiation is reduced, and the coatability is also improved.
Specific examples of the polyfunctional (meth) acrylic compound X include: 1, 6-hexanediol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, triethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1, 9-nonanediol di (meth) acrylate, dimethylol tricyclodecane di (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and the like. The polyfunctional (meth) acrylic compound X may be used alone in 1 kind, or may be used in combination in 2 or more kinds.
The polyfunctional (meth) acrylic compound X may be used in combination with a monofunctional radical polymerizable compound. The content of the polyfunctional (meth) acrylic compound X is, for example, 1 mass% or more and 50 mass% or less, preferably 5 mass% or more and 35 mass% or less, and more preferably 10 mass% or more and 30 mass% or less with respect to the total amount of the radical polymerizable compounds.
The total content of the polyfunctional (meth) acrylic compound is, for example, 1 mass% or more and 50 mass% or less, and preferably 3 mass% or more and 40 mass% or less, based on the total amount of the radical polymerizable compounds.
The content of the radical polymerizable compound in 100% by mass of the light-moisture curable resin composition is preferably 3% by mass or more, more preferably 5% by mass or more, further preferably 10% by mass or more, and further preferably 50% by mass or less, more preferably 40% by mass or less, further preferably 30% by mass or less. When the content of the radical polymerizable compound is not less than the lower limit, the thickness change rate of the cured product in a photocured state can be easily adjusted to be within a predetermined range. When the content of the radical polymerizable compound is not more than the upper limit, the adhesive strength at high temperature is easily improved.
[ photopolymerization initiator ]
The photo-moisture curable resin composition of the present invention contains a photopolymerization initiator. The photocurable resin composition of the present invention can be provided with photocurability by containing a photopolymerization initiator.
Examples of the photopolymerization initiator include: benzophenone-based compounds, acetophenone-based compounds such as α -aminoalkylbenzophenone and α -hydroxyalkylphenone, acylphosphine oxide-based compounds, titanocene-based compounds, oxime ester-based compounds, benzoin ether-based compounds, thioxanthone, and the like. Among these compounds, a compound having an acylphosphine oxide skeleton or a compound having an α -aminoalkylbenzophenone skeleton is preferable from the viewpoint of easily adjusting the thickness change rate of the cured product in the photocured state to a predetermined range.
Among the photopolymerization initiators, commercially available products include, for example: IRGACURE184, IRGACURE369, IRGACURE379EG, IRGACURE651, IRGACURE784, IRGACURE819, IRGACURE907, IRGACURE2959, IRGACURE OXE01, LUCIRIN TPO (all manufactured by BASF corporation), benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether (all manufactured by Tokyo chemical industry Co., Ltd.), and the like.
The content of the photopolymerization initiator in the photocurable resin composition is preferably 0.01 parts by mass or more, more preferably 0.5 parts by mass or more, and further preferably 10 parts by mass or less, more preferably 5 parts by mass or less, per 100 parts by mass of the total amount of the radical polymerizable compound and the moisture-curable urethane resin. When the content of the photopolymerization initiator is within this range, the obtained photo-moisture-curable resin composition is excellent in photocurability and storage stability. Further, when the radical polymerizable compound is within the above range, the radical polymerizable compound is appropriately cured, and the thickness change rate of the cured product in the photocured state can be easily adjusted to be within a predetermined range.
[ moisture-curable urethane resin ]
The light-moisture-curable resin composition of the present invention contains a moisture-curable polyurethane resin. The photocurable resin composition of the present invention has moisture curability by containing a moisture-curable polyurethane resin.
The moisture-curable polyurethane resin 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 to be a raw material of the moisture-curable polyurethane resin, known polyol compounds generally used in the production of polyurethane can be used, and examples thereof include: polyester polyols, polyether polyols, polyalkylene polyols, polycarbonate polyols, and the like. These polyol compounds may be used alone in 1 kind, or may be used in combination in 2 or more kinds.
(moisture-curable polyurethane resin having polyester skeleton)
The photo-moisture-curable resin composition of the present invention contains a moisture-curable polyurethane resin having a polyester skeleton as a moisture-curable polyurethane resin. The high-temperature adhesive strength of the photo-moisture curable resin composition can be improved by including the moisture curable polyurethane resin having a polyester skeleton.
The moisture-curable polyurethane resin having a polyester skeleton can be obtained by reacting a polyester polyol having 2 or more hydroxyl groups in 1 molecule with a polyisocyanate compound having 2 or more isocyanate groups in 1 molecule.
Examples of the polyester polyol include a polyester polyol obtained by a reaction of a polycarboxylic acid and a polyhydric alcohol, 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: phthalic acid, 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, dodecamethylenedicarboxylic acid, and the like. Among them, phthalic acid, terephthalic acid, isophthalic acid, or adipic acid is preferable from the viewpoint of further facilitating improvement of the adhesive strength at high temperatures. These polycarboxylic acids may be used alone in 1 kind, or may be used in combination in 2 or more kinds.
Examples of the polyhydric alcohol which is a raw material of the polyester polyol include: ethylene glycol, 1, 2-propanediol, 1, 3-propanediol, 1, 4-butanediol, neopentyl glycol, 1, 5-pentanediol, 1, 6-hexanediol, diethylene glycol, cyclohexanediol, and the like. Among them, 1, 6-hexanediol or 1, 4-butanediol is preferable from the viewpoint of further facilitating the improvement of the adhesive strength at high temperatures. These polyols may be used alone in 1 kind, or 2 or more kinds may be used in combination.
As the polyisocyanate compound, an aromatic polyisocyanate compound and an aliphatic polyisocyanate compound are suitably used.
Examples of the aromatic polyisocyanate compound include: diphenylmethane diisocyanate, liquid modified diphenylmethane diisocyanate, polymeric MDI, toluene diisocyanate, naphthalene-1, 5-diisocyanate, and the like.
Examples of the aliphatic polyisocyanate compound include: hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, lysine diisocyanate, norbornane diisocyanate, trans-cyclohexane-1, 4-diisocyanate, isophorone diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane diisocyanate, cyclohexane diisocyanate, bis (isocyanate group methyl) cyclohexane, dicyclohexylmethane diisocyanate, and the like.
Among them, diphenylmethane diisocyanate and modified products thereof are preferable from the viewpoint of improving the adhesive strength after complete curing.
The polyisocyanate compounds may be used alone or in combination of 2 or more.
The moisture-curable polyurethane resin having a polyester skeleton may have a polyether skeleton in the molecule. By having a polyether skeleton in the molecule, the viscosity of the photocurable resin composition is easily reduced, and the coatability is easily improved.
The moisture-curable polyurethane resin having a polyether skeleton in a molecule and a polyester skeleton can be obtained by, for example, reacting a polyester polyol having 2 or more hydroxyl groups in 1 molecule, a polyether polyol having 2 or more hydroxyl groups in 1 molecule, and a polyisocyanate compound having 2 or more isocyanate groups in 1 molecule.
As the polyester polyol, the above-mentioned polyester polyol can be used. As the polyether polyol, the following polyether polyols can be used.
(moisture-curable polyurethane resin having polyether skeleton)
In the light-moisture-curable resin composition, it is preferable that the moisture-curable urethane resin contains a moisture-curable urethane resin having a polyether skeleton in addition to the moisture-curable urethane resin having a polyester skeleton. By further including a moisture-curable polyurethane resin having a polyether skeleton, the coatability of the photo-moisture-curable resin composition can be easily improved. The moisture-curable polyurethane resin having a polyether skeleton as used herein is a moisture-curable polyurethane resin not having a polyester skeleton.
The polyurethane resin having a polyether skeleton can be obtained by reacting a polyether polyol having 2 or more hydroxyl groups in 1 molecule with a polyisocyanate compound having 2 or more isocyanate groups in 1 molecule.
Examples of polyether polyols include: ethylene glycol, propylene glycol, a ring-opened polymer of tetrahydrofuran, a ring-opened polymer of 3-methyltetrahydrofuran, a random copolymer or a block copolymer of these or derivatives thereof, a bisphenol polyoxyalkylene modification, and the like. Among these polymers, a ring-opened polymer of propylene glycol or 3-methyltetrahydrofuran is preferable from the viewpoint of easily improving the coatability of the photo-moisture-curable resin composition.
Here, the bisphenol type polyoxyalkylene modification is a polyether polyol obtained by addition reaction of an alkylene oxide (e.g., ethylene oxide, propylene oxide, butylene oxide, isobutane oxide, etc.) to an active hydrogen moiety of a bisphenol type molecular skeleton. The polyether polyol may be a random copolymer or a block copolymer. The bisphenol type polyoxyalkylene modification is preferably one in which 1 or 2 or more alkylene oxides are added to both ends of the bisphenol type molecular skeleton.
The bisphenol type is not particularly limited, and examples thereof include a type, F type, S type, and the like, and bisphenol a type is preferable.
As the polyisocyanate compound, the polyisocyanate compound described above can be used.
The moisture-curable polyurethane resin having a polyether skeleton preferably further contains a product 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 light-moisture-curable resin composition having excellent adhesiveness and a cured product which is flexible and has good elongation can be obtained, and the composition has excellent compatibility with a radical polymerizable compound. In addition, the storage modulus can be easily adjusted to the above-described desired range.
Among these, preferred are compounds using a polyether polyol comprising propylene glycol, a ring-opened polymer of a Tetrahydrofuran (THF) compound, or a ring-opened polymer of a tetrahydrofuran compound having a substituent such as a methyl group, and more preferred is propylene glycol.
In the formula (1), R represents a hydrogen atom, a methyl group or an ethyl group, l is an integer of 0 to 5, m is an integer of 1 to 500, and n is an integer of 1 to 10. l is preferably 0 to 4, m is preferably 50 to 200, and n is preferably 1 to 5. The case where l is 0 means a case where the carbon bonded to R is directly bonded to oxygen.
In the above, the total of n and l is more preferably 1 or more, and still more preferably 1 to 3. R is more preferably a hydrogen atom or a methyl group, and particularly preferably a methyl group.
(other moisture-curable urethane resins)
The light-moisture-curable resin composition of the present invention may contain the moisture-curable polyurethane resin having a polyester skeleton or a moisture-curable polyurethane resin other than the moisture-curable polyurethane resin having a polyether skeleton. Examples of the other moisture-curable urethane resin include a urethane resin having a polyalkylene skeleton, a urethane resin having a polycarbonate skeleton, and the like.
The polyurethane resin having a polyalkylene skeleton can be obtained by reacting a polyalkylene polyol having 2 or more hydroxyl groups in 1 molecule with a polyisocyanate compound having 2 or more isocyanate groups in 1 molecule.
Examples of the polyalkylene polyol include: polybutadiene polyols, hydrogenated polyisoprene polyols, and the like.
As the polyisocyanate compound, the polyisocyanate compound described above can be used.
The polyurethane resin having a polycarbonate skeleton can be obtained by reacting a polycarbonate polyol having 2 or more hydroxyl groups in 1 molecule with a polyisocyanate compound having 2 or more isocyanate groups in 1 molecule.
Examples of the polycarbonate polyol include: polyhexamethylene carbonate polyol, polycyclohexane dimethylene carbonate polyol, and the like.
As the polyisocyanate compound, the polyisocyanate compound described above can be used.
The moisture-curable polyurethane 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, is more preferably a (meth) acryloyl group. The moisture-curable resin having a radical polymerizable functional group is treated as a moisture-curable resin without being contained in the radical polymerizable compound.
The weight average molecular weight of the moisture-curable polyurethane resin is not particularly limited, but is preferably 500 or more, more preferably 1000 or more, and is preferably 10000 or less, more preferably 8000 or less. When the weight average molecular weight is not less than the lower limit, the adhesive strength at high temperature is easily improved. In addition, when the weight average molecular weight is not more than the upper limit, the coatability is easily improved.
In the present specification, the weight average molecular weight and the number average molecular weight are values determined in terms of polystyrene measured by Gel Permeation Chromatography (GPC). As a column for measuring a weight average molecular weight in terms of polystyrene by GPC, Shodex LF-804 (manufactured by Showa Denko K.K.) can be mentioned. Further, tetrahydrofuran is an example of the solvent used in GPC.
The content of the moisture-curable urethane resin in 100% by mass of the light-moisture-curable resin composition is preferably 45% by mass or more, more preferably 50% by mass or more, further preferably 60% by mass or more, and further preferably 95% by mass or less, more preferably 90% by mass or less. When the content of the moisture-curable urethane resin is not less than the lower limit, the adhesive strength at high temperature is easily improved. When the content of the moisture-curable urethane resin is not more than the upper limit, the durability of the adhesive force is easily improved.
The content of the moisture-curable urethane resin having a polyester skeleton in 100% by mass of the light-moisture-curable resin composition is, for example, 25% by mass or more, preferably 30% by mass or more, more preferably 40% by mass or more, further preferably 50% by mass or more, and further preferably 95% by mass or less, more preferably 90% by mass or less. When the content of the moisture-curable urethane resin having a polyester skeleton is not less than the lower limit, the adhesive strength at high temperature is easily improved. When the content of the moisture-curable urethane resin having a polyester skeleton is not more than the upper limit, the durability of the adhesive force is easily improved.
When the light-moisture-curable resin composition contains the moisture-curable urethane resin having a polyester skeleton and another moisture-curable urethane resin, the mass ratio of the content of the other moisture-curable urethane resin to the content of the moisture-curable urethane resin having a polyester skeleton (other moisture-curable urethane resin/moisture-curable urethane resin having a polyester skeleton) is preferably 5 or less, more preferably 3 or less, and further preferably 0.001 or more, more preferably 0.01 or more. When the mass ratio of the content of the other moisture-curable urethane resin is not more than the upper limit, the adhesive strength at high temperature is easily improved. When the mass ratio of the content of the other moisture-curable urethane resin is not more than the upper limit, the durability of the adhesive force is easily improved. The other moisture-curable urethane resin mentioned here is a moisture-curable urethane resin other than the moisture-curable urethane resin having a polyester skeleton, such as a moisture-curable urethane resin having a polyether skeleton.
In the light/moisture-curable resin composition, the mass ratio of the content of the radical polymerizable compound to the moisture-curable urethane resin (radical polymerizable compound/moisture-curable urethane resin) is, for example, 0.04 or more, preferably 0.1 or more, more preferably 0.2 or more, and preferably 1 or less, more preferably 0.8 or less, and further preferably 0.6 or less.
[ non-reactive Polymer ]
The light moisture-curable resin composition of the present invention may further contain a non-reactive polymer. Examples of the non-reactive polymer include: acrylic resins, polyolefin resins, and the like. When the photocurable resin composition of the present invention contains a non-reactive polymer, the thickness change rate of the cured product in a photocured state can be easily adjusted to the above range. The acrylic resin is a polymer of a polymerizable monomer such as a (meth) acrylate.
The method for producing the acrylic resin is not particularly limited, and for example, the acrylic resin can be produced by solution polymerization, suspension polymerization, bulk polymerization, or the like of the polymerizable monomer such as the above radical polymerizable compound.
The weight average molecular weight of the acrylic resin is not particularly limited, but is preferably 10000 or more, and preferably 50000 or less. When the weight average molecular weight is not less than the lower limit, the adhesive strength at high temperature is easily improved. In addition, when the weight average molecular weight is not more than the upper limit, the coatability is easily improved.
The polyolefin resin is not particularly limited, and examples thereof include: polyethylene, polypropylene, and the like. The weight average molecular weight of the polyolefin resin is not particularly limited, but is preferably 10000 or more, and preferably 50000 or less. When the weight average molecular weight is not less than the lower limit, the adhesive strength at high temperature is easily improved. In addition, when the weight average molecular weight is not more than the upper limit, the coatability is easily improved.
The content of the non-reactive polymer in 100% by mass of the photo-moisture-curable resin composition is preferably 5% by mass or more, more preferably 10% by mass or more, and preferably 45% by mass or less, more preferably 40% by mass or less. When the content of the non-reactive polymer is not less than the lower limit, the adhesive strength at high temperature is easily improved. When the content of the non-reactive polymer is not more than the above upper limit, the durability of the adhesive force is easily improved.
[ spacer particles ]
The light-moisture-curable resin composition of the present invention may contain a spacer. When the photo-moisture-curable resin composition of the present invention contains the spacer, the thickness change rate of the cured product in a photo-cured state can be easily adjusted to the above range.
Examples of the spacer particles include resin particles made of a resin, inorganic particles other than metal particles, organic-inorganic hybrid particles, and metal particles. In the present invention, the spacer is preferably a resin particle or an organic-inorganic hybrid particle. The spacer particles may be core-shell particles each including a core and a shell disposed on a surface of the core. The core may be an organic core. The housing may be an inorganic housing. From the viewpoint of relaxing the stress at the bonding portion with the adherend and maintaining the durability of the bonding force at a high level, the spacer particles other than the metal particles are preferable, the resin particles, the inorganic particles other than the metal particles, or the organic-inorganic hybrid particles are more preferable, and the resin particles are even more preferable. If the spacer particles are resin particles, stress can be relaxed when stress is applied to the adhesive portion, and adhesion can be maintained at a high level.
The average particle diameter of the spacer is preferably 50 μm or more, more preferably 80 μm or more, and further preferably 500 μm or less, more preferably 400 μm or less, from the viewpoint of relaxing stress at the bonding portion with the adherend and maintaining durability of the bonding force at a high level.
The above average particle size represents a number average particle size. The average particle diameter of the spacer particles is determined by, for example, observing 50 arbitrary spacer particles with an electron microscope or an optical microscope and calculating the average value.
From the viewpoint of further improving the adhesiveness, the CV value of the particle diameter of the spacer is preferably 10% or less, and preferably 5% or less. The lower limit of the CV value of the particle diameter of the spacer is not particularly limited, but is preferably 1% or more. The CV value (coefficient of variation) is represented by the following formula.
CV value (%) - (ρ/Dn) × 100
ρ: standard deviation of particle diameter of spacer
Dn: average value of particle diameter of spacer
In the case where the light-moisture-curable resin composition of the present invention contains spacer particles, the content of the spacer particles in 100% by mass of the light-moisture-curable resin composition is preferably 1% by mass or more, and more preferably 5% by mass or more, from the viewpoint of further improving the stress relaxation property. In addition, the content of the spacer is preferably 20% by mass or less, and more preferably 15% by mass or less, from the viewpoint of satisfactory coatability.
In addition, when the photo-moisture-curable resin composition contains the spacer, the thickness change rate can be reduced even if the content of the radical polymerizable compound is reduced. From this viewpoint, the content of the radical polymerizable compound in 100% by mass of the light-moisture curable resin composition may be, for example, 20% by mass or less, or may be 3% by mass or more and 10% by mass or less. The mass ratio (radical polymerizable compound/moisture-curable urethane resin) may be 0.2 or less, or may be 0.04 or more and 0.1 or less.
[ Filler ]
The curable resin composition of the present invention may contain a filler. By containing the filler, the curable resin composition of the present invention is likely to have thixotropy and to improve the thin line coatability. The filler may be in the form of particles. In the present specification, the filler means a filler having an average primary particle diameter of less than 1 μm.
The filler is preferably an inorganic filler, and examples thereof include: silica, talc, titanium oxide, zinc oxide, calcium carbonate, and the like. Among these, silica is preferable in terms of excellent ultraviolet light transmittance of the obtained curable resin composition. The filler may be subjected to hydrophobic surface treatment such as silylation treatment, alkylation treatment, and epoxidation treatment. Silica, talc, titanium oxide, and the like have a function of coloring the light-moisture curable resin composition, as in the case of the colorant described below.
The filler can be used alone in 1, also can be combined with more than 2.
The total amount of the filler is, for example, 0.1 part by mass or more, preferably 1 part by mass or more, more preferably 3 parts by mass or more, and preferably 30 parts by mass or less, more preferably 20 parts by mass or less, per 100 parts by mass of the light-moisture curable resin composition.
[ coloring agent ]
The light-moisture curable resin composition of the present invention may contain a colorant. Examples of the colorant include: iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, and the like. Among these colorants, titanium black is preferable. The colorant may be a colorant exhibiting black color, but may be a colorant having another color. The colorant is preferably a material having a capability of transmitting light in the visible light range with difficulty (light-shielding property).
The titanium black has a higher transmittance for light in the vicinity of the ultraviolet region, particularly for light having a wavelength of 360 to 450nm, than the average transmittance for light having a wavelength of 300 to 800 nm. Namely, the titanium black has the following properties: the light-moisture curable resin composition is provided with light-shielding properties by sufficiently shielding light having a wavelength in the visible light region, while transmitting light having a wavelength in the vicinity of the ultraviolet region. Therefore, light-shielding properties can be easily imparted, and the photocurability of the photocurable resin composition can be satisfactorily maintained, while the storage modulus after photocuring can be maintained at a high value.
The total amount of the colorant is, for example, 0.01 parts by mass or more, preferably 0.05 parts by mass or more, more preferably 0.1 parts by mass or more, and preferably 5 parts by mass or less, more preferably 3 parts by mass or less, per 100 parts by mass of the light-moisture curable resin composition.
[ moisture curing accelerating catalyst ]
The photocurable resin composition of the present invention may contain a moisture-curing accelerating catalyst for accelerating the moisture-curing reaction of the moisture-curable polyurethane resin. By using the moisture-curing accelerating catalyst, the moisture-curing property of the photo-moisture-curable resin composition is further improved, and the adhesive strength at high temperature can be further improved.
Specific examples of the moisture-curing accelerating catalyst include tin compounds such as di-n-butyltin dilaurate, di-n-butyltin diacetate, and tin octylate; amine compounds such as triethylamine, 1, 4-diazabicyclo [2.2.2] octane, 2,6, 7-trimethyl-1, 4-diazabicyclo [2.2.2] octane and the like; zinc compounds such as zinc octoate and zinc naphthenate; zirconium tetraacetylacetonate, copper naphthenate, cobalt naphthenate, and the like.
The content of the moisture-curing accelerating catalyst is preferably 0.01 part by mass or more, more preferably 0.1 part by mass or more, and further preferably 5 parts by mass or less, more preferably 3 parts by mass or less, relative to 100 parts by mass of the photo-moisture-curable resin composition. When the content of the moisture-curing accelerating catalyst is within this range, the effect of accelerating the moisture-curing reaction is excellent without deteriorating the storage stability and the like of the photo-moisture-curable resin composition.
[ coupling agent ]
The light-moisture-curable resin composition of the present invention may contain a coupling agent. The adhesive strength is easily improved by containing a coupling agent. Examples of the coupling agent include: silane coupling agents, titanate coupling agents, zirconate coupling agents, and the like. Among them, a silane coupling agent is preferable in terms of having an excellent effect of improving adhesiveness. The coupling agents may be used alone, or 2 or more kinds may be used in combination.
The content of the coupling agent is preferably 0.05 parts by mass or more, more preferably 0.2 parts by mass or more, and further preferably 5 parts by mass or less, more preferably 3 parts by mass or less, relative to 100 parts by mass of the photocurable resin composition. When the content of the coupling agent is within these ranges, the adhesive strength is improved without affecting the storage modulus and the like.
The light-moisture-curable resin composition of the present invention may be diluted with a solvent as necessary. When the photo-moisture-curable resin composition is diluted with a solvent, the parts by mass and% by mass of the photo-moisture-curable resin composition are based on the solid content, that is, the parts by mass and% by mass are parts by mass and% by mass excluding the solvent.
The light-moisture-curable resin composition may contain additives such as wax particles and metal-containing particles in addition to the components described above.
[ method for producing photo-moisture-curable resin composition ]
Examples of the method for producing the light-moisture-curable resin composition of the present invention include the following methods: the radical polymerizable compound, the moisture-curable urethane resin, the photopolymerization initiator, and, if necessary, other additives such as a filler and a colorant are mixed by using a mixer. Examples of the mixer include: a homogeneous dispersion machine, a homomixer, a universal stirrer, a planetary mixer (planetary stirring device), a kneader, a three-roll mill, and the like.
[ method of Using photo-moisture-curable resin composition ]
The light-moisture-curable resin composition of the present invention is a composition that is cured and used as a cured body. Specifically, the photo-moisture curable resin composition of the present invention may be first photo-cured by light irradiation, for example, to be brought into a B-stage state (semi-cured state), and then cured by moisture to be completely cured.
Here, when the photo-moisture curable resin composition is disposed between adherends and the adherends are joined, one adherend may be coated with the photo-moisture curable resin composition, and then the photo-moisture curable resin composition may be photo-cured by light irradiation, for example, to be in a B-stage state, and the other adherend may be superimposed on the photo-moisture curable resin composition in the photo-cured state, and the adherends may be temporarily bonded with an appropriate bonding force (initial bonding force). Then, the moisture-curable urethane resin is cured with moisture in the B-stage state to be completely cured, and the objects stacked via the moisture-curable urethane resin composition are bonded with a sufficient adhesive force.
Here, the light to be irradiated during photocuring is not particularly limited as long as it is light for curing the radical polymerizable compound, and is preferably ultraviolet light. In addition, when the photo-moisture curable resin composition is completely cured by moisture after photo-curing, it may be left in the air for a predetermined time.
The light-moisture-curable resin composition of the present invention is preferably used as an adhesive for electronic parts. Therefore, the adherend is not particularly limited, and various electronic components constituting the electronic device are preferable. Examples of various electronic components constituting an electronic device include various electronic components provided in a display element, a substrate on which the electronic components are mounted, and a semiconductor chip. The material of the adherend may be any of metal, glass, plastic, and the like. The shape of the adherend is not particularly limited, and examples thereof include: film-like, sheet-like, plate-like, panel-like, tray-like, rod (rod-like), box-like, case-like, and the like.
Since the adhesive for electronic components contains a moisture-curable urethane resin having a polyester skeleton, it is sometimes difficult to apply the adhesive at room temperature using a dispenser or the like. Therefore, an example of a method for manufacturing an electronic device using the adhesive for electronic components is a method for manufacturing an electronic device including a step of heating the adhesive for electronic components and a step of applying the heated adhesive for electronic components to electronic components. The temperature in the heating step is, for example, 130 ℃ or lower, preferably 100 ℃ or lower, more preferably 80 ℃ or lower, and preferably 30 ℃ or higher.
As described above, the photocurable resin composition of the present invention is preferably used for bonding electronic parts constituting an electronic device to each other. The photocurable resin composition of the present invention is preferably used for joining an electronic component to another component. With these structures, the electronic component has the cured body of the present invention.
The photocurable resin composition of the present invention is used for, for example, bonding a substrate to obtain an assembly member in an electronic device. The assembled component thus obtained has a first substrate, a second substrate, and the cured body of the present invention, and at least a part of the first substrate is joined to at least a part of the second substrate via the cured body. Further, the first substrate and the second substrate are preferably mounted with at least 1 electronic component, respectively.
Examples
The present invention will be described in further detail with reference to examples, but the present invention is not limited to these examples.
In the present example, the measurement and evaluation of various physical properties were performed as follows.
< Rate of Change of thickness in photocured State >
The photo-moisture-curable resin compositions obtained in examples and comparative examples were applied to a polycarbonate substrate (length 50mm, width 25mm, thickness 2mm) so that the line width was 1.0. + -. 0.1mm, the length was 25. + -. 0.2mm, and the thickness was 0.4. + -. 0.1mm in an atmosphere of 25 ℃ using a dispenser. The light-moisture-curable resin compositions obtained in examples 1,2, 5 to 8 and comparative example 1 were heated at 50 ℃ for 1 hour and then coated, the light-moisture-curable resin composition obtained in example 3 was heated at 120 ℃ for 1 hour and then coated, and the light-moisture-curable resin compositions obtained in example 4 and comparative example 2 were coated at room temperature.
Within 1 minute after the completion of the coating, 1000mJ/cm was irradiated by using UV-LED (wavelength: 365nm)2The ultraviolet ray of (3) causes the photo-moisture curable resin composition to be photo-cured. The thickness immediately after the ultraviolet irradiation was measured and set as the thickness before the application of the load. A glass substrate having the same size as the polycarbonate substrate was placed on the cured product in a photocured state, and a 100g weight was left standing for 10 seconds, thereby applying a load of 0.04MPa to the cured product in a photocured state for 10 seconds. As thickness after application of loadThe thickness of the cured product in the photocured state was measured, and the thickness change rate (%) was measured in the following manner.
Thickness change rate (%) (thickness immediately after light irradiation-thickness after load application)/(thickness immediately after light irradiation) × 100
The thickness of the cured product in the photocured state was observed and measured by a digital microscope (trade name: KH-7800, manufactured by HIROX).
< storage modulus of cured product in photocured State >
3g of the photo-moisture curable resin composition was placed in a UV irradiation rheometer (trade name HAAKE MARS 40/60, manufactured by Thermo Fisher Scientific Co., Ltd.). After the completion of the standing for 30 seconds, 1000mJ/cm was irradiated by using a UV-LED lamp2Ultraviolet rays of (2) to cure it. After 60 seconds of irradiation with ultraviolet light, the shear storage modulus was measured at a frequency F of 1.6Hz in an environment of 25 ℃ and 50 RH%. Further, the UV-LED lamp uses a lamp having a wavelength of 365 nm.
< storage modulus of cured product in light-moisture cured State >
Each of the photo-moisture-curable resin compositions obtained in examples and comparative examples was filled in a Teflon (registered trademark) mold having a width of 3mm, a length of 30mm and a thickness of 1 mm. Within 1 minute after completion of filling, 1000mJ/cm was irradiated by using UV-LED (wavelength 365nm)2The ultraviolet ray of (3) causes the curable resin composition to be photocured. Then, the mixture was allowed to stand at 23 ℃ and 50 RH% for 3 days to be moisture-cured (main curing).
The dynamic viscoelasticity of the obtained cured product was measured at-100 ℃ to 150 ℃ by a dynamic viscoelasticity measuring apparatus (product of IT measurement and control Co., Ltd., product name: DVA-200) to obtain the storage modulus at room temperature (25 ℃). The deformation mode was tensile, the strain was set to 1%, the measurement frequency was 1Hz, and the temperature rise rate was 5 ℃/min.
< viscosity >
The viscosities of the photo-moisture-curable resin compositions obtained in examples and comparative examples were measured at 25 ℃ and a rotation speed of 1rpm using a cone and plate VISCOMETER ("VISCOMETER TV-22" manufactured by Toyobo industries Co., Ltd.).
< high temperature adhesion (adhesion at 100 ℃) >
As shown in FIGS. 1(a) and (b), each of the photo-moisture curable resin compositions 10 obtained in examples and comparative examples was coated on a glass plate 11 so as to have a width of 0.4. + -. 0.05mm, a length of 25. + -. 2mm and a thickness of 0.2. + -. 0.05 mm. Within 1 minute after the completion of the coating, 1000mJ/cm was irradiated by using UV-LED (wavelength: 365nm)2The curable resin composition 10 is photo-cured by the ultraviolet ray of (2). Then, the glass plate 12 was stacked and a 100g weight was left standing for 10 seconds, and a load of 0.04MPa was applied to the cured product in the photo-cured state for 10 seconds. Then, a 100g weight was removed, and the plate was allowed to stand at 23 ℃ and 50 RH% for 3 days to be moisture-cured (main-cured) to prepare a sample 13 for evaluation. The prepared evaluation sample 13 was pulled at a speed of 12mm/sec in the shear direction S by a tensile tester under an environment of 100 ℃ and 50% RH, and the strength when the glass plate 11 and the glass plate 12 were peeled was measured to measure the adhesive strength at 100 ℃. The adhesion force thus measured was evaluated according to the following evaluation criteria.
A: more than 35N
B: 20N or more and less than 35N
C: less than 20N
< stress relaxation Property (Cold-Heat cycle test) >
A sample for evaluation 13 was produced in the same manner as in the above-described evaluation of high-temperature adhesiveness, except that the glass plate 11 was changed to a polycarbonate plate. The evaluation samples were subjected to 1000 cycles of a cooling-heating cycle test in which 1000 cycles of 30 minutes at-40 ℃ and 30 minutes at 80 ℃ were performed. The samples for evaluation before and after the cold and hot tests were pulled at a speed of 12mm/sec in the shear direction S using a tensile tester under an environment of 25 ℃ and 50% RH, and the strength when the polycarbonate plate and the glass plate 12 were peeled was measured to measure the adhesion at 25 ℃.
The stress relaxation property of the photo-moisture curable resin composition was evaluated from the adhesive strength before the cold-heat cycle test and the adhesive strength after the cold-heat cycle test according to the following evaluation criteria.
[ evaluation standards ]
A: (adhesion force after thermal and cold cycles)/(adhesion force before thermal and cold cycles) ≧ 0.8
B: 0.8 > (adhesion after thermal and cold cycles)/(adhesion before thermal and cold cycles) ≧ 0.6
C: 0.6 > (adhesion after thermal and cold cycles)/(adhesion before thermal and cold cycles) ≧ 0.4
D: 0.4 > (adhesion after Cold and Heat cycle)/(adhesion before Cold and Heat cycle)
< coatability >
The photo-moisture-curable resin compositions obtained in examples and comparative examples were evaluated for coatability at room temperature, 50 ℃ and 120 ℃ using an air dispenser (ML-5000XII, manufactured by Kyowa Kagaku Co., Ltd.). As an evaluation method, each of the photo-moisture curable resin compositions was filled in a 10mL syringe (manufactured by tibetan gaku corporation), and after being left in an oven set at each temperature for 1 hour, whether or not the thin line coating was possible was evaluated under the following standard discharge conditions.
The components used: precision nozzle HN-0.4N (available from Wucang Hi science and technology Co., Ltd., inner diameter 0.40mm)
Ejection pressure: 0.3MPa
[ evaluation standards ]
1: can be coated at normal temperature
2: can be coated at 50 deg.C
3: can be coated at 120 deg.C
The moisture-curable polyurethane resins used in the examples and comparative examples were prepared according to the following synthesis examples 1 to 4.
The moisture-curable urethane resin 1 having a polyester skeleton was produced according to the following synthesis example 1.
[ Synthesis example 1]
100 parts by mass of a polyester polyol (a polycondensation product of adipic acid and 1, 6-hexanediol, and a polyol having an alcohol terminal) as a polyol compound and 0.01 part by mass of dibutyltin dilaurate were put in a separable flask having a capacity of 500mL, and the mixture was stirred at 100 ℃ for 30 minutes under vacuum (20mmHg or less) to mix them. Then, 30 parts by mass of diphenylmethane diisocyanate (product name "Pure MDI", manufactured by Nissan Co., Ltd.) as a polyisocyanate compound was added thereto under normal pressure, and the mixture was stirred at 80 ℃ for 3 hours to effect a reaction, thereby obtaining a moisture-curable polyurethane resin 1 having a polyester skeleton (weight-average molecular weight 5000).
The moisture-curable polyurethane resin 2 having a polyester skeleton was produced in accordance with the following synthesis example 2.
[ Synthesis example 2]
100 parts by mass of a polyester polyol (a polyester polyol obtained from adipic acid, 1, 6-hexanediol, and isophthalic acid as main components, an aromatic ring concentration of 15% by mass, and a weight average molecular weight of 1000) as a polyol compound and 0.01 part by mass of dibutyltin dilaurate were charged in a separable flask having a capacity of 500 mL. The mixture was stirred at 100 ℃ for 30 minutes under vacuum (20mmHg or less) to mix. Then, 52.5 parts by mass of diphenylmethane diisocyanate (product name "Pure MDI", manufactured by Nissan Co., Ltd.) as a polyisocyanate compound was added thereto under normal pressure, and the mixture was stirred at 80 ℃ for 3 hours to effect a reaction, thereby obtaining a moisture-curable polyurethane resin 2 having a polyester skeleton. The weight average molecular weight of the obtained moisture-curable polyurethane resin was 1500.
The moisture-curable polyurethane resin 1 having a polyether skeleton was produced according to synthesis example 3 below.
[ Synthesis example 3]
100 parts by mass of polypropylene glycol (product name "EXCENOL 2020", manufactured by Asahi glass-ceramic Co., Ltd.) as a polyol compound and 0.01 part by mass of dibutyltin dilaurate were put in a separable flask having a capacity of 500mL, and the mixture was stirred at 100 ℃ for 30 minutes under vacuum (20mmHg or less) to mix them. Then, 26.5 parts by mass of diphenylmethane diisocyanate (trade name "Pure MDI", manufactured by Nissan Co., Ltd.) as a polyisocyanate compound was added under normal pressure, and the mixture was stirred at 80 ℃ for 3 hours to effect a reaction, thereby obtaining a moisture-curable polyurethane resin 1 having a polyether skeleton (weight-average molecular weight 2900).
The moisture-curable polyurethane resin 2 having a polyether skeleton was produced according to the following synthesis example 4.
[ Synthesis example 4]
100 parts by mass of polytetramethylene ether glycol (product of Mitsubishi chemical corporation, trade name: PTMG-2000) as a polyol compound and 0.01 part by mass of dibutyltin dilaurate were charged in a separable flask having a capacity of 500mL, and the mixture was stirred at 100 ℃ for 30 minutes under vacuum (20mmHg or less) to mix them. Then, 26.5 parts by mass of diphenylmethane diisocyanate (product name "Pure MDI", manufactured by Nissan Co., Ltd.) as a polyisocyanate compound was added under normal pressure, and the mixture was stirred at 80 ℃ for 3 hours to effect a reaction, thereby obtaining a moisture-curable polyurethane resin 2 having a polyether skeleton (weight-average molecular weight 2700).
The components other than the moisture-curable urethane resin used in each of examples and comparative examples are shown below.
Urethane acrylate: "EBECRYL 8411" manufactured by DAICEL-ALLNEX, 2-FUNCTIONAL
Tetrahydrofurfuryl acrylate: "LIGHT ACRYLATE THF-A" manufactured by Kyoeisha chemical Co., Ltd., monofunctional
Stearyl acrylate: "SR 257" manufactured by Sartomer corporation, monofunctional
3,3, 5-trimethylcyclohexyl acrylate: VISCOAT #196, available from Osaka organic chemical industries, and Single-functional
1, 6-hexanediol diacrylate: "LIGHT ACRYLATE1, 6-HX-A", manufactured by Kyoeisha chemical Co., Ltd., 2-functional group
Trimethylolpropane triacrylate: "LIGHT ACRYLATE TMP-A", manufactured by Kyoeisha chemical Co., Ltd., 3-functional group
Photopolymerization initiator: 2-benzyl-2-dimethylamino-1- (4-quinolinylphenyl) -butan-1-one (manufactured by BASF, IRGACURE 369')
Coupling agent: 3-Acryloxypropyltrimethoxysilane, "KBM-5103", manufactured by shin-Etsu chemical Co., Ltd "
Filling agent: trimethylsilylated silica (manufactured by Nippon Aerosil, "R812", primary particle diameter 7nm)
Spacer particles: resin particles (available from Water-collecting chemical Co., Ltd. "MICROPEARL GS-L250"; average particle diameter (table) 250.0. + -. 12.5. mu.m; CV value (table) about 7%)
Colorant: titanium black
Examples 1 to 8 and comparative examples 1 and 2
The respective materials were stirred at a temperature of 50 ℃ by a planetary stirring apparatus (product of THINKY, "debubbling stirring taro") in the mixing ratios shown in table 1, and then uniformly mixed at a temperature of 50 ℃ by a ceramic three-roll mill to obtain the photo-moisture curable resin compositions of examples 1 to 3 and comparative examples 1 and 2.
[ Table 1]
As shown in the above examples, it is understood that the photo-moisture curable resin composition containing the moisture curable urethane resin having a polyester skeleton can exhibit good high-temperature adhesion. Further, it is found that when the thickness change rate is 50% or less, the stress relaxation property becomes good, and the durability of the adhesive force becomes good.
Claims (12)
1. A photo-moisture curable resin composition comprising a radical polymerizable compound, a moisture curable urethane resin and a photopolymerization initiator,
the moisture-curable urethane resin includes a moisture-curable urethane resin having a polyester skeleton,
for the light passing through 1000mJ/cm2The cured product in a state of being photocured by ultraviolet rays of (1) has a thickness change rate of 50% or less before and after application of a load of 0.04 MPa.
2. The photo-moisture-curable resin composition according to claim 1, having a viscosity of 3000 Pa-s or less at 25 ℃ and 1 rpm.
3. The photo-moisture-curable resin composition according to claim 1 or 2, the moisture-curable urethane resin further comprising a moisture-curable urethane resin having a polyether skeleton.
4. The photo-moisture-curable resin composition according to claim 1 or 2, wherein the moisture-curable urethane resin having a polyester skeleton has a polyether skeleton in a molecule.
5. The photo-moisture curable resin composition according to any one of claims 1 to 4, which comprises a spacer.
6. The photo-moisture-curable resin composition according to any one of claims 1 to 5, wherein a content of the radical polymerizable compound in 100% by mass of the photo-moisture-curable resin composition is 3% by mass or more.
7. The photo-moisture-curable resin composition according to any one of claims 1 to 6, wherein the photopolymerization initiator is a compound having an acylphosphine oxide skeleton or a compound having an α -aminoalkylbenzophenone skeleton.
8. The photo-moisture-curable resin composition according to any one of claims 1 to 7, wherein a cured product in a photo-cured state has a storage modulus at 25 ℃ of 10kPa or more.
9. The photo-moisture curable resin composition according to any one of claims 1 to 8, wherein a cured product obtained by allowing the photo-cured product to stand in an environment of 23 ℃ and 50 RH% for 3 days has a storage modulus at 25 ℃ of 1MPa or more.
10. An adhesive for electronic parts, which is prepared from the photo-moisture-curable resin composition according to any one of claims 1 to 9.
11. A method of manufacturing an electronic device, comprising:
a step of heating the adhesive for electronic parts according to claim 10, and
and applying the heated adhesive for electronic components to electronic components.
12. A cured product of the photo-moisture-curable resin composition according to any one of claims 1 to 9.
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| JP2020-017770 | 2020-02-05 | ||
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| JP2020128734 | 2020-07-29 | ||
| PCT/JP2021/003989 WO2021157624A1 (en) | 2020-02-05 | 2021-02-03 | Photo/moisture curable resin composition, adhesive for electronic components, method for producing electronic component, and cured body |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008248152A (en) * | 2007-03-30 | 2008-10-16 | Dic Corp | Moisture-hardening polyurethane hot-melt adhesive and fixture material using it |
| JP2016074826A (en) * | 2014-10-07 | 2016-05-12 | Dic株式会社 | Method for producing laminate and decorative fixture member |
| US20160215185A1 (en) * | 2013-09-26 | 2016-07-28 | Kunshan Tianyang Hot Melt Adhesive Co., Ltd. | Preparation method for moisture-curing polyurethane reactive hot melt adhesive for textile composition |
| CN107075061A (en) * | 2015-04-09 | 2017-08-18 | 积水化学工业株式会社 | Light wet-cured type resin combination, electronic component-use bonding agent and display element bonding agent |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR101882197B1 (en) | 2014-12-22 | 2018-07-26 | (주)에스엔피월드 | Impregnated NBR(nitrile butadiene rubber) sponge of gel form cosmetic composition and method of preparing the same |
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- 2021-02-03 KR KR1020227008921A patent/KR20220137865A/en unknown
- 2021-02-03 CN CN202180005424.5A patent/CN114423834A/en active Pending
- 2021-02-03 WO PCT/JP2021/003989 patent/WO2021157624A1/en active Application Filing
- 2021-02-04 TW TW110104256A patent/TW202134309A/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008248152A (en) * | 2007-03-30 | 2008-10-16 | Dic Corp | Moisture-hardening polyurethane hot-melt adhesive and fixture material using it |
| US20160215185A1 (en) * | 2013-09-26 | 2016-07-28 | Kunshan Tianyang Hot Melt Adhesive Co., Ltd. | Preparation method for moisture-curing polyurethane reactive hot melt adhesive for textile composition |
| JP2016074826A (en) * | 2014-10-07 | 2016-05-12 | Dic株式会社 | Method for producing laminate and decorative fixture member |
| CN107075061A (en) * | 2015-04-09 | 2017-08-18 | 积水化学工业株式会社 | Light wet-cured type resin combination, electronic component-use bonding agent and display element bonding agent |
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| JPWO2021157624A1 (en) | 2021-08-12 |
| KR20220137865A (en) | 2022-10-12 |
| TW202134309A (en) | 2021-09-16 |
| WO2021157624A1 (en) | 2021-08-12 |
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