WO2022210671A1 - 硬化性接着剤組成物、及び硬化物 - Google Patents

硬化性接着剤組成物、及び硬化物 Download PDF

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Publication number
WO2022210671A1
WO2022210671A1 PCT/JP2022/015341 JP2022015341W WO2022210671A1 WO 2022210671 A1 WO2022210671 A1 WO 2022210671A1 JP 2022015341 W JP2022015341 W JP 2022015341W WO 2022210671 A1 WO2022210671 A1 WO 2022210671A1
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Prior art keywords
adhesive composition
curable adhesive
mass
component
cured product
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PCT/JP2022/015341
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English (en)
French (fr)
Japanese (ja)
Inventor
健太 西嶋
幹広 樫尾
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Lintec Corp
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Lintec Corp
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Priority to JP2023511354A priority Critical patent/JPWO2022210671A1/ja
Priority to CN202280025745.6A priority patent/CN117098825A/zh
Priority to KR1020237026434A priority patent/KR20230164004A/ko
Publication of WO2022210671A1 publication Critical patent/WO2022210671A1/ja
Anticipated expiration legal-status Critical
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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
    • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
    • C09J123/26—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers modified by chemical after-treatment
    • C09J123/30—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers modified by chemical after-treatment by oxidation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C08K5/3492—Triazines
    • C08K5/34924—Triazines containing cyanurate groups; Tautomers thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C08L71/12—Polyphenylene oxides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
    • 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
    • C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
    • C09J171/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C09J171/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C09J171/12—Polyphenylene oxides
    • 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
    • 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
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • C09J201/02—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/35—Heat-activated
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/22—Secondary treatment of printed circuits
    • H05K3/28—Applying non-metallic protective coatings
    • H05K3/281—Applying non-metallic protective coatings by means of a preformed insulating foil

Definitions

  • the present invention relates to a curable adhesive composition that gives a cured product with excellent low dielectric properties in a high frequency range and that does not easily contaminate the surroundings during the bonding process, and the cured product thereof.
  • the high frequency region refers to the region from 300 MHz to 300 GHz.
  • An FPC can be obtained, for example, by etching the copper foil of an insulating resin film such as polyimide (copper-clad laminate) to form an electric circuit. Moreover, usually, a coverlay film having an insulating resin base material and an adhesive layer is attached to a copper foil having an electric circuit formed thereon to protect the electric circuit.
  • Patent Document 1 discloses an adhesive composition containing a styrene-based elastomer, a modified polyphenylene ether resin, an epoxy resin, and an epoxy resin curing agent, and a thermosetting adhesive layer made of this adhesive composition on a substrate. Formed thermosetting adhesive sheets are described. Patent Document 1 also describes that the adhesive composition has a low dielectric constant and a low dielectric loss tangent.
  • the adhesive composition and its cured product described in Patent Document 1 have low dielectric properties (in this specification, “low dielectric properties” means “low dielectric constant and low dielectric loss tangent”. ).
  • low dielectric properties means “low dielectric constant and low dielectric loss tangent”.
  • the fluidity before curing is too high, which can cause contamination of the surroundings during the bonding process.
  • the present invention has been made in view of the above circumstances, and provides a curable adhesive composition that gives a cured product excellent in low dielectric properties in a high frequency region and does not easily contaminate the surroundings in the bonding process, and a cured product thereof. intended to provide
  • curable adhesive compositions [1] to [10] and cured products [11] to [15] are provided.
  • [11] A cured product obtained by curing the curable adhesive composition according to any one of [1] to [10].
  • a curable adhesive composition that gives a cured product with excellent low dielectric properties in a high frequency range and that does not easily contaminate the surroundings in the bonding process, and a cured product thereof.
  • FIG. 2 is a schematic diagram (plan view) of a part of a laminate used when evaluating the exudation of an adhesive component.
  • FIG. 2 is a schematic diagram showing a cross section taken along line AA of FIG. 1;
  • the number average molecular weight (Mn) can be obtained as a standard polystyrene conversion value by performing gel permeation chromatography (GPC) using tetrahydrofuran (THF) as a solvent.
  • GPC gel permeation chromatography
  • THF tetrahydrofuran
  • the cross-linking reaction involving the binder resin (A) and the cross-linking agent (B) is referred to as “curing reaction (I)", and the cured product obtained mainly through the progress of curing reaction (I) is referred to as " It may be described as “cured product (I)”.
  • the cured product (I) should be cured at least to such an extent that exudation of the adhesive component in the coating film is suppressed. Therefore, the cured product (I) may be one in which the curing reaction (I) is almost completed, or contains an unreacted binder resin (A) and a cross-linking agent (B), and has undergone the curing reaction (I). It may have curability derived from it.
  • the curable adhesive composition of the present invention contains a curable component other than the binder resin (A) and the cross-linking agent (B) (hereinafter sometimes referred to as “curable component (X)”). good too.
  • the curable component (X) is a compound that participates in the curing reaction (I)
  • the curable component (X) is a compound that does not participate in the curing reaction (I), even if the curing reaction (I) is almost completed, the resulting cured product (I) is not affected by the curable component (X).
  • the curable adhesive composition containing the curable component (X) that does not participate in the curing reaction (I) can ensure multiple curing reactions without highly controlling the curing reaction (I). It is possible to more reliably prevent the adhesive component from oozing out of the coating film.
  • the curable component (X) includes the following components (C), (D) and (F).
  • Component (C) Non-aromatic curable compound that is liquid at 25° C.
  • Component (D) Polyphenylene ether resin having a reactive functional group
  • Component (F) Silane coupling agent
  • the curable adhesive composition of one embodiment of the present invention may further contain the following component (E).
  • the curable adhesive composition of one embodiment of the present invention further includes components other than the above components (A) to (F), as long as the effects of the present invention are not impaired. may contain ingredients.
  • the total content of components (A) to (E) is based on the total amount (100% by mass) of active ingredients in the curable adhesive composition, 45% by mass or more, 55% by mass or more, 65% by mass or more, 75% by mass or more, 80% by mass or more, 85% by mass or more, 90% by mass or more, or 95% by mass or more, or 100% by mass below, it is good also as 99.9 mass % or less, or 99.8 mass % or less.
  • the curable adhesive composition of the present invention contains, as component (A), a binder resin having a reactive functional group (hereinafter sometimes referred to as "binder resin (A)"). Since the curable adhesive composition of the present invention contains the binder resin (A), contamination of the surroundings during the adhesion process can be suppressed, as will be described later. Binder resin (A) can be used individually by 1 type or in combination of 2 or more types.
  • the number average molecular weight (Mn) of the binder resin (A) is not particularly limited. 000, more preferably 10,000 to 100,000.
  • the number average molecular weight (Mn) of the binder resin (A) can be obtained as a standard polystyrene conversion value by performing gel permeation chromatography (GPC) using tetrahydrofuran (THF) as a solvent, and specific measurement The conditions are as described above.
  • binder resin (A) examples include polyolefin-based resins, phenoxy-based resins, polyimide-based resins, polyamideimide-based resins, polyvinyl butyral-based resins, and polycarbonate-based resins. Among these, polyolefin-based resins are preferable as the binder resin (A). When the binder resin (A) is a polyolefin resin, it becomes easier to obtain a curable adhesive composition that gives a cured product with excellent low dielectric properties.
  • the curable adhesive composition may contain a binder resin other than the polyolefin resin as another component. good.
  • the content of the other binder resin is preferably 0 to 50 parts by mass, more preferably 0 to 30 parts by mass, and still more preferably 100 parts by mass of the total polyolefin resin. 0 to 10 parts by weight, more preferably 0 to 5 parts by weight.
  • a polyolefin resin is a polymer containing repeating units derived from an olefin monomer.
  • the polyolefin resin may be a polymer consisting only of repeating units derived from an olefinic monomer, or a repeating unit derived from an olefinic monomer and a monomer copolymerizable with the olefinic monomer. It may be a polymer composed of repeating units derived from
  • the olefinic monomer is preferably an ⁇ -olefin having 2 to 8 carbon atoms, more preferably ethylene, propylene, 1-butene, isobutylene, or 1-hexene, and still more preferably ethylene or propylene.
  • These olefinic monomers can be used singly or in combination of two or more.
  • monomers copolymerizable with olefinic monomers include vinyl acetate, (meth)acrylic acid esters, and styrene.
  • (meth)acrylic acid means acrylic acid or methacrylic acid (same below).
  • Polyolefin resins include very low density polyethylene (VLDPE), low density polyethylene (LDPE), medium density polyethylene (MDPE), high density polyethylene (HDPE), linear low density polyethylene, polypropylene (PP), ethylene-propylene Copolymers, olefinic elastomers (TPO), ethylene-vinyl acetate copolymers (EVA), ethylene-(meth)acrylic acid copolymers, ethylene-(meth)acrylic acid ester copolymers, and the like.
  • VLDPE very low density polyethylene
  • LDPE low density polyethylene
  • MDPE medium density polyethylene
  • HDPE high density polyethylene
  • PP polypropylene
  • TPO ethylene-propylene Copolymers
  • EVA ethylene-vinyl acetate copolymers
  • EVA ethylene-(meth)acrylic acid copolymers
  • ethylene-(meth)acrylic acid ester copolymers and the like.
  • Reactive functional groups contained in the binder resin (A) include a carboxy group, a carboxylic acid anhydride group, a carboxylic acid ester group, a hydroxyl group, an epoxy group, an amide group, an ammonium group, a nitrile group, an amino group, an imide group, and an isocyanate group. group, acetyl group, thiol group, ether group, thioether group, sulfone group, phosphon group, nitro group, urethane group, halogen atom, alkoxysilyl and the like.
  • Binder resin (A) is preferably a modified resin.
  • the modified resin is a resin into which a reactive functional group is introduced, which is obtained by modifying a resin as a precursor using a modifying agent.
  • a modifier used for modifying the binder resin is a compound having a reactive functional group in the molecule. Reactive functional groups include those previously described.
  • modified resins include resins into which acid groups have been introduced (acid-modified resins) and resins into which hydroxyl groups have been introduced, and acid-modified resins are preferred.
  • acid-modified resins resins into which an acid anhydride structure is introduced are preferable.
  • a resin is reacted with an unsaturated carboxylic acid or an unsaturated carboxylic anhydride (hereinafter sometimes referred to as "unsaturated carboxylic acid or the like") to form a carboxy group or a carboxylic anhydride group. is introduced (graft modification).
  • unsaturated carboxylic acid or an unsaturated carboxylic anhydride hereinafter sometimes referred to as "unsaturated carboxylic acid or the like
  • Unsaturated carboxylic acids to be reacted with the resin include unsaturated carboxylic acids such as maleic acid, fumaric acid, itaconic acid, citraconic acid, glutaconic acid, tetrahydrophthalic acid, and aconitic acid; maleic anhydride, itaconic anhydride, and glutaconic anhydride. acids, unsaturated carboxylic anhydrides such as citraconic anhydride, aconitic anhydride, norbornene dicarboxylic anhydride, and tetrahydrophthalic anhydride; These can be used individually by 1 type or in combination of 2 or more types. Among these, maleic anhydride is preferable because it is easy to obtain a curable adhesive composition that gives a cured product with higher adhesive strength.
  • the amount of the unsaturated carboxylic acid or the like to be reacted with the resin is preferably 0.1 to 5 parts by mass, more preferably 0.2 to 3 parts by mass, and still more preferably 0.2 to 1 part by mass with respect to 100 parts by mass of the resin. part by mass.
  • the method of introducing unsaturated carboxylic acid units or unsaturated carboxylic anhydride units into the resin is not particularly limited.
  • a radical generator such as organic peroxides or azonitriles, a resin and an unsaturated carboxylic acid, etc.
  • a method of heating and melting above the melting point of the resin to react or a method of reacting the resin and the unsaturated carboxylic acid.
  • the resin is graft-copolymerized with an unsaturated carboxylic acid or the like by heating and stirring in the presence of a radical generator.
  • a modified polyolefin resin is a polyolefin resin into which a reactive functional group has been introduced, obtained by modifying a polyolefin resin as a precursor using a modifier.
  • the curable adhesive composition contains, as another component, a binder resin other than the acid-modified polyolefin resin.
  • a binder resin other than the acid-modified polyolefin resin may be included in the curable adhesive composition.
  • the content of the other binder resin is preferably 0 to 50 parts by mass, more preferably 0 to 30 parts by mass, and more preferably 0 to 30 parts by mass, based on 100 parts by mass of the total amount of the acid-modified polyolefin resin. It is preferably 0 to 10 parts by weight, and more preferably 0 to 5 parts by weight.
  • Component (B) a cross-linking agent having a molecular weight of 1000 or less, which can react with the component (A)]
  • the curable adhesive composition of the present invention contains, as the component (B), a cross-linking agent having a molecular weight of 1,000 or less that can react with the component (A) (hereinafter sometimes referred to as "cross-linking agent (B)". ). Since the curable adhesive composition of the present invention contains the cross-linking agent (B), contamination of the surroundings during the adhesion process can be suppressed, as will be described later.
  • a crosslinking agent (B) can be used individually by 1 type or in combination of 2 or more types.
  • the content of the cross-linking agent (B) (the total amount of these when two or more cross-linking agents (B) are included) is 0 with respect to the total amount (100% by mass) of the active ingredients of the curable adhesive composition. .1% by mass or more, preferably 0.2% by mass or more, more preferably 0.3% by mass or more, even more preferably 0.5% by mass or more, even more preferably 0.7% by mass or more, and particularly preferably is 0.9% by mass or more, and is preferably 5% by mass or less, more preferably 4% by mass or less, even more preferably 3% by mass or less, and even more preferably 2% by mass or less.
  • the content of the cross-linking agent (B) is 0.1% by mass or more relative to the total amount of active ingredients in the curable adhesive composition, it is possible to obtain a curable adhesive composition that does not easily stain the surroundings. .
  • the content of the cross-linking agent (B) is 5% by mass or less with respect to the total amount of active ingredients in the curable adhesive composition, so that the curable adhesive composition gives a cured product having excellent low dielectric properties. easier to obtain.
  • the content of the cross-linking agent (B) is preferably 0.1 part by mass or more, more preferably 100 parts by mass of component (A) 0.3 parts by mass or more, more preferably 0.5 parts by mass or more, still more preferably 0.8 parts by mass or more, particularly preferably 1.2 parts by mass or more, and preferably 10 parts by mass or less, more It is preferably 7 parts by mass or less, more preferably 5 parts by mass or less, and even more preferably 3 parts by mass or less.
  • Cross-linking agent (B) is a compound capable of reacting with component (A). Therefore, as the cross-linking agent (B), it is necessary to appropriately select one having a reactive group or a reactive site that is reactive with the reactive functional group in the binder resin (A).
  • the cross-linking agent (B) an isocyanate-based cross-linking agent, an epoxy-based cross-linking agent, a metal chelate-based cross-linking agent, an aziridine-based cross-linking agent, or the like can be used.
  • one or more selected from isocyanate-based cross-linking agents, epoxy-based cross-linking agents, and metal chelate-based cross-linking agents are preferable from the viewpoint of storage stability.
  • a cross-linking agent ( B) is preferably one or more selected from isocyanate-based cross-linking agents, epoxy-based cross-linking agents, and metal chelate-based cross-linking agents.
  • An isocyanate-based cross-linking agent is a compound having two or more isocyanate groups in the molecule.
  • isocyanate cross-linking agents include 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hydrogenated tolylene diisocyanate, hydrogenated xylene diisocyanate, 1,5-pentamethylene diisocyanate, and 1,6-hexamethylene.
  • Epoxy crosslinking agent is a compound having two or more epoxy groups in its molecule.
  • Epoxy crosslinking agents include 1,3-bis(N,N-diglycidylaminomethyl)cyclohexane, N,N,N',N'-tetraglycidyl-m-xylylenediamine, ethylene glycol diglycidyl ether, 1 ,6-hexanediol diglycidyl ether, trimethylolpropane diglycidyl ether, diglycidylaniline, diglycidylamine and the like.
  • a metal chelate-based cross-linking agent is a chelate compound having metal ions functioning as cross-linking points.
  • metal chelate-based cross-linking agents for example, metal chelate compounds whose metal ions are aluminum ions, zirconium ions, titanium ions, zinc ions, iron ions, tin ions, and the like can be used. Among these, aluminum chelate compounds are preferred.
  • aluminum chelate compounds include aluminum tris(acetylacetonate), acetylacetonate aluminum bis(ethylacetoacetate), diisopropoxyaluminum monooleyl acetoacetate, monoisopropoxyaluminum bisoleyl acetoacetate, and the like.
  • the cross-linking agent (B) is preferably a compound having an isocyanurate skeleton, more preferably a compound having an isocyanurate skeleton and two or more isocyanate groups.
  • the cross-linking agent (B) is a compound having an isocyanurate skeleton, it becomes easier to obtain a curable adhesive composition that gives a cured product with excellent low dielectric properties.
  • the component (B) is a curable adhesive composition that is a compound having an isocyanurate skeleton
  • the curable adhesive composition contains, as another component, a cross-linking compound other than the compound having an isocyanurate skeleton. It may contain an agent.
  • the content of the other cross-linking agent is preferably 0 to 100 parts by mass, more preferably 0 to 50 parts by mass, with respect to 100 parts by mass of the total amount of the compound having an isocyanurate skeleton. More preferably 0 to 30 parts by mass, still more preferably 0 to 10 parts by mass, and particularly preferably 0 to 5 parts by mass.
  • a curable adhesive composition that gives a cured product having excellent low dielectric properties can be easily obtained.
  • an isocyanurate of a polyisocyanate compound is more preferred, and an isocyanurate of 1,5-pentamethylene diisocyanate [1,3,5-tris(5-isocyanatopentyl)-1,3,5-triazine-2, 4,6-trione] or isocyanurate of 1,6-hexamethylene diisocyanate [1,3,5-tris(6-isocyanatohexyl)-1,3,5-triazine-2,4,6-trione] More preferred.
  • the cross-linking agent (B) is a compound that can react with the binder resin (A), the binder resin (A) and the cross-linking agent ( B) can be reacted to build a crosslinked structure in the coating film.
  • a coating film having a crosslinked structure inside is difficult to fluidize even when heated. Therefore, by building a cross-linked structure in the coating film before adhering the two adherends, even if heat treatment is performed when adhering the two adherends, staining of the adhesive component in the coating film can be prevented.
  • the coating film can be completely cured while suppressing extrusion.
  • the curable adhesive composition of the present invention by appropriately controlling the reaction between the binder resin (A) and the cross-linking agent (B), contamination of the surroundings during the adhesion process can be suppressed. .
  • Component (C) non-aromatic curable compound that is liquid at 25°C
  • Component (C) is a non-aromatic curable compound that is liquid at 25° C. (hereinafter sometimes referred to as “curable compound (C)”). Curable compound (C) can be used individually by 1 type or in combination of 2 or more types.
  • the curable compound (C) is a curable compound. Therefore, when the curable compound (C) is the curable component (X) that does not participate in the curing reaction (I), the curable adhesive composition containing the curable compound (C) causes the curing reaction (I). The resulting cured product can undergo curing reaction (II) and can function as a solid adhesive.
  • the curable compound (C) is a compound that is liquid at 25°C. Therefore, when the curable compound (C) is the curable component (X) that does not participate in the curing reaction (I), the curable adhesive composition containing the curable compound (C) causes the curing reaction (I).
  • the solid adhesive composed of the resulting cured product has good wettability and spreadability during lamination processing, and is more excellent in lamination aptitude.
  • "Liquid at 25°C” means having fluidity at 25°C.
  • a compound that is liquid at 25° C. is a compound with a viscosity of 2 to 10000 mPa ⁇ s measured at 25° C. and 1.0 rpm using an E-type viscometer.
  • the curable compound (C) is a non-aromatic compound.
  • a non-aromatic compound means a compound without an aromatic ring. Since the curable compound (C) is a non-aromatic compound, the cured product of the curable adhesive composition containing the curable compound (C) tends to have excellent low dielectric properties.
  • the curable compound (C) is preferably a compound having a heterocyclic skeleton.
  • the curable compound (C) is a compound having a heterocyclic skeleton, it becomes easier to obtain a curable adhesive composition that gives a cured product with excellent adhesive strength and low dielectric properties.
  • the component (C) is a curable adhesive composition that is a compound having a heterocyclic skeleton, the curable adhesive composition contains, as another component, a curable compound other than the compound having the heterocyclic skeleton. It may contain a compound.
  • the content of the other curable compound is preferably 0 to 50 parts by mass, more preferably 0 to 30 parts by mass, relative to 100 parts by mass of the total amount of the compound having a heterocyclic skeleton. parts, more preferably 0 to 10 parts by weight, and even more preferably 0 to 5 parts by weight.
  • the heterocyclic skeleton includes an isocyanurate skeleton and a glycoluril skeleton.
  • the heterocyclic skeleton preferably has an n-fold rotation axis as a symmetry element.
  • a cured product of a curable adhesive composition containing such a curable compound (C) having a heterocyclic skeleton tends to have excellent low dielectric properties.
  • the molecular weight of the curable compound (C) is preferably 1,000 or less, more preferably 800 or less, still more preferably 650 or less, and even more preferably 500 or less. Curable compounds with a molecular weight of 1,000 or less tend to meet the requirement of being liquid at 25°C. Moreover, the molecular weight of the curable compound (C) is preferably 100 or more, more preferably 200 or more, and even more preferably 275 or more. The curable compound (C) having a molecular weight of 100 or more is less likely to volatilize during the drying process and heat curing process of the curable adhesive composition, so that a cured product having desired physical properties can be easily obtained.
  • the number of carbon atoms in the hydrocarbon group having a double bond at the end contained in the curable compound (C') is preferably 2-10, more preferably 2-5.
  • Hydrocarbon groups having a double bond at the end include vinyl group, allyl group, 3-butenyl group, 4-pentenyl group, 5-hexenyl group, isopropenyl group, 1-methyl-2-propenyl group and vinylbenzyl group. , a vinyl naphthyl group, and the like. Among these, an allyl group is preferred.
  • the number of hydrocarbon groups having a double bond at the terminal contained in the curable compound (C') is two or more.
  • the number of hydrocarbon groups having a double bond at the terminal is 2 or more, it becomes easier to obtain a curable adhesive composition that gives a cured product with excellent adhesive strength and heat resistance.
  • the number of hydrocarbon groups having a double bond at the end is preferably 2-4, more preferably 2.
  • curable compound (C') examples include a curable compound (C') having an isocyanurate skeleton and a curable compound (C') having a glycoluril skeleton.
  • curable compound (C') having an isocyanurate skeleton examples include compounds represented by the following formula (1) or (2).
  • R 1 and R 2 each independently represent a hydrocarbon group having a double bond at the end;
  • R 3 is a saturated hydrocarbon group having 1 to 15 carbon atoms; represents an alkoxy group-substituted alkyl group.
  • R 4 to R 6 each independently represent a hydrocarbon group having a double bond at its end.
  • hydrocarbon groups having a double bond at the end represented by R 1 , R 2 , R 4 , R 5 and R 6 are as explained above.
  • the saturated hydrocarbon group represented by R 3 has 1 to 15 carbon atoms, preferably 5 to 15 carbon atoms, and more preferably 8 to 15 carbon atoms.
  • saturated hydrocarbon groups represented by R 3 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, t-butyl group, s-butyl group, isobutyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, etc. is mentioned.
  • curable compound (C') having a glycoluril skeleton examples include compounds represented by the following formula (3).
  • a compound having an isocyanurate skeleton is preferable as the curable compound (C′), since a cured product having an appropriate crosslink density and excellent low dielectric properties can be easily obtained.
  • a compound represented by is more preferable, and a compound represented by the following formula is even more preferable.
  • R represents a saturated hydrocarbon group having 5 to 15 carbon atoms, preferably a saturated hydrocarbon group having 8 to 15 carbon atoms.
  • the content of the curable compound (C) (the total amount when two or more curable compounds (C) are included) is preferably 5% by mass or more, more preferably 7% by mass or more, still more preferably 8.5% by mass or more, relative to the total amount (100% by mass) of the active ingredients of the curable adhesive composition, and , preferably 25% by mass or less, more preferably 20% by mass or less, and still more preferably 15% by mass or less.
  • the content of the curable compound (C) is 5% by mass or more based on the total amount of active ingredients in the curable adhesive composition, it becomes easier to obtain a curable adhesive composition that provides a cured product with excellent adhesive strength.
  • the content of the curable compound (C) is 25% by mass or less in the total amount of active ingredients in the curable adhesive composition, it is easy to obtain a curable adhesive composition that gives a cured product having excellent low dielectric properties. Become.
  • the content of the curable compound (C) (two or more curable compounds (C)
  • the total amount of these when containing) is preferably 3 parts by mass or more, more preferably 5 parts by mass or more, still more preferably 7 parts by mass or more, still more preferably 10 parts by mass or more, and preferably 30 It is not more than 25 parts by mass, more preferably not more than 20 parts by mass, and even more preferably not more than 16 parts by mass.
  • Polyphenylene ether resin (D) is a compound having a polyphenylene ether skeleton and a reactive functional group. Since the polyphenylene ether resin (D) has a polyphenylene ether skeleton, the cured product of the curable adhesive composition containing the polyphenylene ether resin (D) is excellent in low dielectric properties. Moreover, since the polyphenylene ether resin (D) has a reactive functional group, the cured product of the curable adhesive composition containing the polyphenylene ether resin (D) has excellent heat resistance. Polyphenylene ether resin (D) can be used individually by 1 type or in combination of 2 or more types.
  • Examples of the polyphenylene ether skeleton in the polyphenylene ether resin (D) include those represented by the following formula (4).
  • X is a divalent group represented by the following formula (5) or formula (6)
  • each Y is independently a divalent group represented by the following formula (7) is a group
  • a and b are integers of 0 to 100, and at least one of a and b is 1 or more.
  • * represents a bond (same below).
  • R 13 to R 20 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group, preferably a hydrogen atom or a methyl group.
  • R 21 to R 28 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group, preferably a hydrogen atom or a methyl group.
  • A represents a linear, branched or cyclic divalent hydrocarbon group having 20 or less carbon atoms.
  • the polyphenylene ether resin (D) a resin having a reactive functional group at both ends of the polyphenylene ether skeleton is preferable because a cured product having excellent low dielectric properties can be easily obtained.
  • the component is a curable adhesive composition that is a resin having a reactive functional group at both ends of the polyphenylene ether skeleton
  • the curable adhesive composition contains, as another component, the polyphenylene ether skeleton
  • Other polyphenylene ether resins other than resins having reactive functional groups at both ends may be contained.
  • the content of the other polyphenylene ether resin is preferably 0 to 50 parts by mass with respect to 100 parts by mass of the total amount of the resin having reactive functional groups at both ends of the polyphenylene ether skeleton. , more preferably 0 to 30 parts by mass, still more preferably 0 to 10 parts by mass, and even more preferably 0 to 5 parts by mass.
  • the polyphenylene ether resin (D) can be obtained by forming a polyphenylene ether skeleton and then introducing a reactive functional group to the terminal.
  • a polyphenylene ether resin (D) having vinylbenzyl groups at both ends as reactive functional groups was reacted with a bifunctional phenol compound and a monofunctional phenol compound to obtain a polymer having phenolic hydroxyl groups at both ends. Then, it can be obtained by vinylbenzyl etherifying the terminal phenolic hydroxyl group using 4-(chloromethyl)styrene.
  • the content of the polyphenylene ether resin (D) (when two or more (D) components are included, the total amount of these) is Preferably 1% by mass or more, more preferably 5% by mass or more, still more preferably 10% by mass or more, still more preferably 15% by mass, relative to the total amount (100% by mass) of the active ingredients in the curable adhesive composition or more, preferably 30% by mass or less, more preferably 25% by mass or less.
  • the content of the polyphenylene ether resin (D) is 1% by mass or more in the total amount of active ingredients of the curable adhesive composition, it is easy to obtain a curable adhesive composition that gives a cured product having excellent low dielectric properties. Become. When the content of the polyphenylene ether resin (D) is 30% by mass or less in the total amount of active ingredients of the curable adhesive composition, it becomes easier to impart sticking properties.
  • the curable adhesive composition of the present invention may contain a silane coupling agent (F) as a curable component (X).
  • the silane coupling agents (F) can be used singly or in combination of two or more.
  • silane coupling agent (F) organosilicon compounds having at least one alkoxysilyl group in the molecule are preferred.
  • Silane coupling agents (F) include 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyl Silane coupling agents having a (meth)acryloyl group such as roxypropyltrimethoxysilane; Silane coupling agents having a vinyl group such as vinyltrimethoxysilane, vinyltriethoxysilane, dimethoxymethylvinylsilane, diethoxymethylvinylsilane, trichlorovinylsilane, vinyltris(2-methoxyethoxy)silane; 2-(3,4-epoxycyclohexyl
  • the content of the silane coupling agent (F) (when two or more silane coupling agents (F) are included, the total amount of these) is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, and still more preferably 0.08% by mass or more, relative to the total amount (100% by mass) of the active ingredients of the curable adhesive composition and is preferably 5% by mass or less, more preferably 3% by mass or less, even more preferably 1% by mass or less, and even more preferably 0.5% by mass or less.
  • the content of the silane coupling agent (F) is 0.01% by mass or more based on the total amount of active ingredients in the curable adhesive composition, it becomes easier to maintain the adhesiveness after the high-temperature and high-humidity test.
  • the content of the silane coupling agent (F) is 5% by mass or less in the total amount of active ingredients in the curable adhesive composition, it becomes easier to maintain the adhesiveness after the high temperature and high humidity test.
  • the content of the silane coupling agent (F) (two or more silane coupling agents
  • the total amount of these when containing (F)) is preferably 0.01 parts by mass or more, more preferably 0.05 parts by mass or more, still more preferably 0.1 parts by mass or more, and even more preferably 0.15 It is at least 3 parts by mass, preferably 3 parts by mass or less, more preferably 1 part by mass or less, still more preferably 0.7 parts by mass or less, and even more preferably 0.5 parts by mass or less.
  • the quaternary ammonium salts include tetrabutylammonium tetrafluoroborate, tetrabutylammonium hexafluorophosphate, tetrabutylammonium hydrogensulfate, tetraethylammonium tetrafluoroborate, tetraethylammonium p-toluenesulfonate, N,N-dimethyl-N- benzylanilinium hexafluoroantimonate, N,N-dimethyl-N-benzylanilinium tetrafluoroborate, N,N-dimethyl-N-benzylpyridinium hexafluoroantimonate, N,N-diethyl-N-benzyltrifluoromethanesulfonate , N,N-dimethyl-N-(4-methoxybenzyl)pyridinium hexafluoroantimonate,
  • iodonium salts include diphenyliodonium hexafluoroarsinate, bis(4-chlorophenyl)iodonium hexafluoroarsinate, bis(4-bromophenyl)iodonium hexafluoroarsinate, phenyl(4-methoxyphenyl)iodonium hexafluoroarsinate, and the like. is mentioned.
  • the content of the cationic polymerization initiator (E) (when two or more (E) components are included, the total amount of these) is a cationic Preferably 0.01 parts by mass or more, more preferably 0.05 parts by mass or more, still more preferably 0.1 parts by mass with respect to a total of 100 parts by mass of components (C) and (D), which are polymerizable compounds Above, more preferably 0.2 parts by mass or more, preferably 6 parts by mass or less, more preferably 5 parts by mass or less, and even more preferably 4 parts by mass or less.
  • the content of the cationic polymerization initiator is 0.01 parts by mass or more, it becomes easier to prevent a decrease in reactivity.
  • the content of the cationic polymerization initiator is 6 parts by mass or less, it becomes easy to suppress corrosion of the adherend.
  • the method of using the curable adhesive composition of the present invention is not particularly limited.
  • the curable adhesive composition of the present invention is applied to one adherend, the resulting coating film is dried, and the curing reaction (I) proceeds to form a cured product (I).
  • another adherend is superimposed on the cured product (I), and these adherends can be adhered by further curing the coating film.
  • the curing reaction (I) started to build a crosslinked structure in the coating film is stopped in the middle, the unreacted binder resin (A) in the cured product (I) and the cross-linking agent (B) can be used to restart the curing reaction (I) to bond the two adherends together.
  • the cured product (I) contains a curable component (X) that does not participate in the curing reaction (I)
  • the curing reaction (II) can be used to bond two adherends together. .
  • Examples of methods for applying the curable adhesive composition include spin coating, spray coating, bar coating, knife coating, roll coating, blade coating, die coating, and gravure coating.
  • the thickness of the coating film is not particularly limited, it is usually 1 to 50 ⁇ m, preferably 1 to 25 ⁇ m, more preferably 5 to 25 ⁇ m.
  • the curable adhesive composition of the present invention provides a cured product having a dielectric loss tangent of less than 0.0050 at 23° C. and a frequency of 1 GHz by curing the curable adhesive composition, and 0.0030 or less.
  • Those that give a cured product are preferred, those that give a cured product of 0.0020 or less are more preferred, those that give a cured product of 0.0015 or less are more preferred, those that give a cured product of 0.0012 or less are even more preferred, Those that give a cured product of 0.0010 or less are more preferred, and those that give a cured product of 0.0008 or less are particularly preferred.
  • the dielectric loss tangent it is usually 0.0001 or more.
  • the curable adhesive composition of the present invention preferably gives a cured product having a dielectric constant of 3.00 or less at 23° C. and a frequency of 1 GHz by curing the curable adhesive composition, and preferably 2.75 or less. more preferably give a cured product of 2.50 or less. Although there is no particular lower limit for the dielectric constant under these conditions, it is usually 2.00 or more.
  • the cured state of the sample used for the measurement of the dielectric loss tangent and the dielectric constant is not limited as long as the measurement is possible. For example, it may or may not have additional curability.
  • An example of a sample for measurement of the dielectric loss tangent and relative permittivity is a sheet-like adhesive after being subjected to a heat treatment at 100° C. for 2 minutes as a drying treatment and curing reaction (I).
  • the curable adhesive composition of the present invention provides a cured product having the above-described dielectric properties through a curing reaction. It is preferably used as a material for forming members, insulating members, and the like.
  • the cured product of the present invention is characterized in that the raw material composition is the curable adhesive composition of the present invention. That is, the cured product of the present invention is a product in which at least the curing reaction (I) proceeds and the viscosity of the curable adhesive composition increases or solidifies.
  • Cured product Cured product ( ⁇ 1) A cured product whose raw material composition is a curable adhesive composition capable of performing curing reaction (I) and curing reaction (II) as a curing reaction, at least curing reaction (II Cured product having curability derived from )
  • Cured product ( ⁇ 2) A cured product whose raw material composition is a curable adhesive composition capable of performing only the curing reaction (I) as a curing reaction, wherein the curing reaction (I ) is completed and does not have further curability.
  • the cured product ( ⁇ 1) and the cured product ( ⁇ 1) are cured products having curability.
  • the cured product ( ⁇ 1) and cured product ( ⁇ 1) are useful as solid adhesives. It is preferable that these hardened products have thermosetting properties because the bonding process can be performed efficiently.
  • the thermosetting cured product preferably has a sheet-like shape. Since the thermosetting cured product has a sheet-like shape, two adherends can be efficiently adhered by heat press treatment or the like.
  • thermosetting sheet adhesives Sheet-shaped thermosetting cured products are protected on one or both sides for protection during storage and transportation. It may have a seat or the like.
  • thermosetting sheet adhesive of the present invention uses the curable adhesive composition of the present invention as a raw material composition. Therefore, the cured product obtained by curing the thermosetting sheet adhesive of the present invention is excellent in low dielectric properties. Therefore, the thermosetting sheet-like adhesive of the present invention is suitably used as a sheet-like adhesive for electronic devices and a sheet-like adhesive for coverlay films.
  • Sheet-like adhesives for electronic devices are sheet-like adhesives used for bonding various parts in electronic devices and for protecting and insulating circuits in electronic devices.
  • Examples of electronic devices include communication devices such as smartphones and tablet terminals.
  • a sheet-like adhesive for a coverlay film is a sheet-like adhesive used when manufacturing a coverlay film.
  • a coverlay film is, for example, a laminated film used to protect the surface of a flexible printed wiring board, and usually has an insulating resin layer and an adhesive layer.
  • the thermosetting sheet adhesive of the present invention is useful as this adhesive layer.
  • the cured product ( ⁇ 2) and the cured product ( ⁇ 2) are non-curing products.
  • the cured product ( ⁇ 2) and the cured product ( ⁇ 2) the cured product ( ⁇ 1) and the cured product ( ⁇ 1) function as an adhesive and are in a completely cured state, or the curable adhesive composition of the present invention. Examples include a molded article obtained by completely curing an object.
  • Binder resin (A1) maleic anhydride-modified ⁇ -olefin polymer [manufactured by Mitsui Chemicals, trade name: UNISTOL H-200, number average molecular weight: 47,000]
  • Isocyanate-based cross-linking agent (B1) 1,3,5-tris(5-isocyanatopentyl)-1,3,5-triazine-2,4,6-trione [manufactured by Mitsui Chemicals, Inc., trade name: Stabio D-370N, molecular weight: 462]
  • Binder resin (A1) 100 parts by mass, isocyanate cross-linking agent (B1) 0.5 parts by mass, curable compound (C1) 12.5 parts by mass, polyphenylene ether resin (D1) 25 parts by mass, cationic polymerization initiator (E1) 0.12 parts by mass and 0.2 parts by mass of the silane coupling agent (F1) were dissolved in toluene to prepare a curable adhesive composition.
  • the obtained curable adhesive composition is applied on the release-treated surface of a release sheet (first release sheet, manufactured by Lintec Corporation, trade name: SP-PET752150) to form a coating film, and the resulting coating is The film was dried at 100° C.
  • An adhesive sheet was obtained by laminating the release-treated surface of another release sheet (second release sheet, product name: SP-PET381130, manufactured by Lintec Corporation) on the exposed surface of the adhesive layer.
  • second release sheet product name: SP-PET381130, manufactured by Lintec Corporation
  • FIG. 1 is a schematic plan view of the laminated body used for evaluating the exudation of the adhesive component in the examples after being subjected to a heat press treatment. As shown in FIG.
  • the maximum value X of the distance between the oozing adhesive component 2 and the polyimide film 3 when viewed from the top is defined as "the oozing length of the adhesive component", and is shown in Table 1. described.
  • the cured products of the curable adhesive compositions obtained in Examples 1 to 5 and Comparative Example 1 are all excellent in low dielectric properties.
  • a heat press treatment was performed under the conditions of 171° C., 1.38 MPa, and 20 minutes, and the adhesive component oozed out to a large extent.
  • the curable adhesive compositions of Examples 1 to 5 contain the cross-linking agent (B), the coating film of the curable adhesive composition was dried at 100°C or heat laminated at 100°C. A crosslinked structure is formed in the coating film by performing the treatment. Therefore, even if the heat press treatment is performed under the conditions of 171° C., 1.38 MPa, and 20 minutes, the exudation of the adhesive component is suppressed.

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