Composition, cured product, and method for producing the cured product
The composition of a cyclic ether component, an ionic latent curing agent, and an elastomer component addresses the issues of precipitation and poor adhesion in thermosetting compositions, achieving excellent storage stability, electrical properties, and adhesive strength.
Patent Information
- Application Number
- JP2020059867
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Filing Date
- 2020-03-30
- Publication Date
- 2025-04-10
- Estimated Expiration
- 2040-03-30
AI Technical Summary
Existing thermosetting compositions containing epoxy compounds face issues such as precipitation or aggregation of the curing agent, leading to poor formation of cured products with excellent electrical properties and adhesive strength.
A composition comprising a cyclic ether component, a latent curing agent that is an ionic compound, and an elastomer component, where the elastomer content is at least 30 parts by mass, achieving a balance of storage stability, electrical properties, and adhesion.
The composition exhibits excellent balance of storage stability, electrical properties, and adhesive strength, preventing precipitation and aggregation of the latent curing agent, and ensuring efficient curing and adhesion.
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Abstract
Description
[Technical field]
[0001] The present disclosure relates to a composition having excellent storage stability, electrical properties and adhesive strength. [Background technology]
[0002] Epoxy compound-containing curable compositions are used in the fields of inks, paints, various coating agents, adhesives, optical members, and the like. For example, Patent Document 1 describes a thermosetting composition containing an epoxy compound. It also describes a method of laminating this thermosetting composition with copper foil. Specifically, it describes a method of impregnating a glass cloth with the thermosetting composition, laminating it with copper foil, and then heating and curing it. [Prior art documents] [Patent documents]
[0003] [Patent Document 1] JP 2011-046815 A Summary of the Invention [Problem to be solved by the invention]
[0004] However, the thermosetting composition described in Patent Document 1 has problems such as the occurrence of precipitation or aggregation of the epoxy curing agent, and the inability to form a cured product having excellent electrical properties and adhesive strength.
[0005] The present disclosure has been made in consideration of the above problems, and has as its main object to provide a composition that has an excellent balance of storage stability, electrical properties, and adhesive strength. [Means for solving the problem]
[0006] Means for Solving the Problems The present inventors have conducted intensive research to solve the above problems and have found that a composition containing a cyclic ether component, a latent curing agent, and an elastomer component, in which the latent curing agent is an ionic compound and the content of the elastomer component is a predetermined amount, has an excellent balance of storage stability, electrical properties, and adhesive strength, thereby completing the present disclosure.
[0007] That is, the present disclosure provides a polymerizable composition comprising a cyclic ether component and A latent hardener; An elastomer component; Including, the latent curing agent is an ionic compound, The present invention provides a composition in which the content of the elastomer component is 30 parts by mass or more per 100 parts by mass of the total of the cyclic ether component, the latent curing agent, and the elastomer component.
[0008] According to the present disclosure, the composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0009] In the present disclosure, it is preferable that the elastomer contains a polymer including a structural unit having an aromatic ring in a side chain, because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0010] In the present disclosure, it is preferable that the cyclic ether component contains at least one of an aromatic epoxy compound and an aliphatic epoxy compound containing an aliphatic ring, because the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0011] In the present disclosure, it is preferable to contain a nitrogen-containing heterocyclic cation, because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0012] In the present disclosure, the anion of the ionic compound preferably contains at least one of a cyanate-based anion and a carboxylate-based anion, because the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0013] In the present disclosure, the content of the ionic compound is preferably 0.1 parts by mass or more and 30 parts by mass or less in 100 parts by mass of the total of the cyclic ether component and the ionic compound, because the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0014] In the present disclosure, the composition preferably contains a resin having a phenylene ether skeleton, because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0015] The present disclosure provides a cured product of the above-described composition.
[0016] According to the present disclosure, since the above-mentioned composition is used, the adhesive strength is excellent and, for example, there is little variation in the adhesive strength when viewed in a plan view.
[0017] The present disclosure provides a method for producing a cured product, comprising a curing step of curing the cyclic ether components in the composition together.
[0018] According to the present disclosure, since the above-mentioned composition is used, a cured product having excellent electrical properties and adhesive strength can be obtained. Effect of the Invention
[0019] The present disclosure has an effect of providing a composition that has an excellent balance of storage stability, electrical properties, and adhesive strength. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0020] The present disclosure relates to a composition, a cured product thereof, and a method for producing the cured product. The composition, cured product, and method for producing the cured product according to the present disclosure will be described in detail below.
[0021] A. Composition First, the composition of the present disclosure will be described. The composition of the present disclosure comprises a cyclic ether component, a latent curing agent, and an elastomer component, wherein the latent curing agent is an ionic compound, and the content of the elastomer component is 30 parts by mass or more in a total of 100 parts by mass of the cyclic ether component, the latent curing agent, and the elastomer component.
[0022] According to the present disclosure, the composition has an excellent balance of storage stability, electrical properties, and adhesive strength. The reason why the composition has an excellent balance of storage stability, electrical properties and adhesive strength is presumed to be as follows.
[0023] That is, the latent curing agent used in the composition is an ionic compound and has excellent compatibility with the cyclic ether component, the solvent, etc. Therefore, for example, even when the composition has a low viscosity, precipitation, aggregation, etc. of the latent curing agent is suppressed, and the composition has excellent storage stability. In addition, as described above, the ionic compound contained as the latent curing agent has high compatibility with the cyclic ether component and the like and is easily dispersed or dissolved uniformly in the composition, so that the curing reaction between the cyclic ether components can proceed efficiently and excellent adhesive strength can be exhibited. Furthermore, by containing a specified amount of elastomer, the composition can exhibit excellent electrical properties such as a low relative dielectric constant and a low dielectric loss tangent when cured. For these reasons, the composition has an excellent balance of storage stability, electrical properties and adhesive strength.
[0024] The composition of the present disclosure comprises a cyclic ether component, a latent curing agent, and an elastomer component. Each component of the composition of the present disclosure will be described below.
[0025] 1. Latent hardener The latent curing agent used in the present disclosure is an ionic compound. The latent curing agent herein may be one which has no activity towards the cyclic ether component at 25° C., but which becomes activated by the application of a stimulus such as heating, thereby accelerating curing. The activation temperature of the latent curing agent that is activated by heating may be higher than 25° C., but is preferably from 60° C. to 250° C., and more preferably from 80° C. to 200° C. This is because the composition has excellent curability.
[0026] The ionic compound used as the latent hardener is a salt of a cation and an anion. The ionic compound may be an ionic liquid compound or an ionic solid compound, but is preferably an ionic liquid compound. The composition in which the ionic compound is an ionic liquid compound has a better balance of storage stability, electrical properties, and adhesive strength. The ionic liquid compound refers to an ionic compound that is liquid at 25°C and atmospheric pressure. The ionic solid compound refers to an ionic compound that is solid at 25°C and atmospheric pressure.
[0027] Examples of the cation of the ionic compound include a nitrogen-containing heterocyclic cation, a tetraalkylphosphonium cation, a tetraalkylammonium cation, and a trialkylsulfonium cation.
[0028] The nitrogen-containing heterocyclic cation refers to a cation consisting of a heterocyclic ring or a derivative thereof containing a nitrogen atom as a ring skeleton atom. The nitrogen-containing heterocyclic ring can be a ring consisting of nitrogen atoms and carbon atoms as ring skeleton atoms, or a ring consisting of nitrogen atoms, carbon atoms and oxygen atoms, and preferably a ring consisting of nitrogen atoms and carbon atoms as ring skeleton atoms. This is because the composition has a better balance of storage stability, electrical properties and adhesive strength.
[0029] Specific examples of the nitrogen-containing heterocyclic cation include nitrogen-containing aromatic heterocyclic cations such as imidazolium cation, pyrazolium cation, pyridinium cation, and pyrimidinium cation, etc. Specific examples of the nitrogen-containing aliphatic heterocyclic cations include piperidinium cation and pyrrolidinium cation.
[0030] In the present disclosure, the cation preferably contains a nitrogen-containing heterocyclic cation, more preferably contains a nitrogen-containing aromatic heterocyclic cation, particularly preferably a nitrogen-containing aromatic heterocyclic cation containing two nitrogen atoms on the ring or a cation of a nitrogen-containing aromatic heterocyclic ring which is a five-membered ring, more preferably a nitrogen-containing aromatic heterocyclic ring containing two nitrogen atoms on the ring which is a five-membered ring, and particularly preferably contains an imidazolium cation or a derivative thereof. This is because the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0031] The derivative of an imidazolium cation refers to a cation in which a hydrogen atom bonded to an atom constituting the ring skeleton of an imidazolium cation is substituted with a substituent. The imidazolium cation and its derivatives include the cation represented by the following general formula (1).
[0032] [ka]
[0033] (In the formula, R 1 and R 2 each independently represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an alkenyl group having 2 to 12 carbon atoms, R 3 , R 4 , and R 5 are each independently a hydrogen atom or an alkyl group having 1 to 12 carbon atoms.
[0034] R 1 , R 2 , R 3 , R 4and R 5 Examples of the alkyl group having 1 to 12 carbon atoms used in the above include linear or cyclic alkyl groups. Examples of linear or branched alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, amyl, isoamyl, t-amyl, hexyl, heptyl, octyl, isooctyl, 2-ethylhexyl, t-octyl, nonyl, isononyl, decyl, isodecyl, undecyl, and dodecyl. Examples of cyclic alkyl groups include cycloalkyl groups and cycloalkylalkyl groups. Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, adamantyl, decahydronaphthyl, octahydropentalene, and bicyclo[1.1.1]pentanyl groups. Examples of the cycloalkylalkyl group include cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cycloheptylmethyl, cyclooctylmethyl, cyclononylmethyl, cyclodecylmethyl, 2-cyclobutylethyl, 2-cyclopentylethyl, 2-cyclohexylethyl, 2-cycloheptylethyl, 2-cyclooctylethyl, 2-cyclononylethyl, 2-cyclodecylethyl, 3-cyclobutylpropyl, 3-cyclopentylpropyl, 3-cyclohexylpropyl, 3-cycloheptylpropyl, 3-cyclooctylpropyl, 3-cyclononylpropyl, 3-cyclodecylpropyl, 4-cyclobutylbutyl, and 4-cyclopentylbutyl.
[0035] R 1 and R 2Examples of the alkenyl group having 2 to 12 carbon atoms used in the above include a vinyl group, an allyl group, a 3-butenyl group, a 2-butenyl group, a 4-pentenyl group, a 3-pentenyl group, a 2-hexenyl group, a 3-hexenyl group, a 5-hexenyl group, a 2-heptenyl group, a 3-heptenyl group, a 4-heptenyl group, a 3-octenyl group, a 3-nonenyl group, a 4-decenyl group, a 3-undecenyl group, a 4-dodecenyl group, a 3-cyclohexenyl group, a 2,5-cyclohexadienyl-1-methyl group, and a 4,8,12-tetradecatrienyl allyl group.
[0036] R 1 is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and particularly preferably an alkyl group having 1 to 3 carbon atoms, because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength. R 2 is preferably an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, more preferably an alkyl group having 2 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms, particularly preferably an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 4 carbon atoms, and most preferably an alkyl group having 2 to 5 carbon atoms. This is because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength. R 4 , R 5 is preferably a hydrogen atom, because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength. R 3 is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and more preferably a hydrogen atom, because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength. R 1 ~R 5When any of the above groups is an alkyl group, the alkyl group is preferably a chain alkyl group, because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0037] Specific examples of the imidazolium cation and its derivatives include 1,3-dimethylimidazolium cation, 1,3-diethylimidazolium cation, 1-ethyl-3-methylimidazolium cation, 1-propyl-3-methylimidazolium ion, 1-butyl-3-methylimidazolium cation, 1-hexyl-3-methylimidazolium cation, 1-octyl-3-methylimidazolium cation, 1-decyl-3-methylimidazolium cation, 1-dodecyl-3-methylimidazolium cation, 1-tetradecyl-3-methylimidazolium cation, 1,2-dimethyl-3-propylimidazolium cation, 1-ethyl-2,3-dimethylimidazolium cation, 1-butyl-2,3-dimethylimidazolium cation, 1-hexyl-2,3-dimethylimidazolium cation, and 1-allyl-3-methylimidazolium cation. Among them, at least one selected from 1,3-dimethylimidazolium cation, 1,3-diethylimidazolium cation, 1-ethyl-3-methylimidazolium cation, 1-propyl-3-methylimidazolium ion, 1-butyl-3-methylimidazolium cation and 1-allyl-3-methylimidazolium cation is preferred, because the composition has a better balance of storage stability, electrical properties and adhesive strength.
[0038] Examples of the pyrazolium cation and its derivatives include a 1-methylpyrazolium cation and a 3-methylpyrazolium cation. Examples of pyridinium cations and derivatives thereof include 1-ethylpyridinium cation, 1-butylpyridinium cation, 1-(3-hydroxypropyl)pyridinium cation, 1-ethyl-3-methylpyridinium cation, 1-butyl-3-methylpyridinium cation, 1-butyl-4-methylpyridinium cation, 1-(3-cyanopropyl)pyridinium cation, 1,3-dimethyl-1,4,5,6-tetrahydropyrimidinium cation, 1,2,3-trimethyl-1,4,5,6-tetrahydropyrimidinium cation, 1,2,3,4-tetramethyl-1,4,5,6-tetrahydropyrimidinium cation, and 1,2,3,5-tetramethyl-1,4,5,6-tetrahydropyrimidinium cation. Examples of pyrimidinium cations and derivatives thereof include 1,3-dimethyl-1,4-dihydropyrimidinium cation, 1,3-dimethyl-1,6-dihydropyrimidinium cation, 1,2,3-trimethyl-1,4-dihydropyrimidinium cation, 1,2,3-trimethyl-1,6-dihydropyrimidinium cation, 1,2,3,4-tetramethyl-1,4-dihydropyrimidinium cation, and 1,2,3,4-tetramethyl-1,6-dihydropyrimidinium cation. Examples of the piperidinium cation and its derivatives include a 1-butyl-1-methylpiperidinium cation and a 1-methyl-1-propylpiperidinium cation. Examples of pyrrolidinium cations and derivatives thereof include 1,1-dimethylpyrrolidinium cation, 1-methyl-1-ethylpyrrolidinium cation, 1-methyl-1-propylpyrrolidinium cation, 1-methyl-1-butylpyrrolidinium cation, 1-methyl-1-pentylpyrrolidinium cation, 1-methyl-1-hexylpyrrolidinium cation, 1-methyl-1-heptylpyrrolidinium cation, 1-ethyl-1-propylpyrrolidinium cation, 1-ethyl-1-butylpyrrolidinium cation, and 1-ethyl-1-pentylpyrrolidinium cation.
[0039] Examples of the tetraalkylphosphonium cation include a tributylethylphosphonium cation, a tetrahexylphosphonium cation, a triethylmethylphosphonium cation, a trimethyldecylphosphonium cation, and a trihexyltetradecylphosphonium cation. Examples of the tetraalkylammonium cation include tetramethylammonium cation, tetraethylammonium cation, tetrabutylammonium cation, tetrahexylammonium cation, triethylmethylammonium cation, tributylethylammonium cation, trimethyldecylammonium cation, trihexyltetradecylammonium cation, (2-hydroxyethyl)trimethylammonium cation, N,N-diethyl-N-(2-methoxyethyl)-N-methylammonium [DEME] cation, tris(2-hydroxyethyl)methylammonium cation, N,N-trimethyl-N-propylammonium [TMPA] cation, trimethyl(1H,1H,2H,2H-heptadecafluorodecyl)ammonium cation, trimethyl-(4-vinylbenzyl)ammonium cation, and 2-(methacryloyloxy)ethyltrimethylammonium. Examples of the trialkylsulfonium cation include a diethylmethylsulfonium cation, a dibutylethylsulfonium cation, and a dimethyldecylsulfonium cation.
[0040] Examples of anions of ionic compounds include halide ions, metal chloride anions, cyanate anions, carboxylate anions, sulfonate anions, sulfonyl anions, other fluoride anions, and ClO4 - , NO3 - etc.
[0041] In the present disclosure, the anion is preferably at least one of a cyanate-based anion and a carboxylate-based anion, and more preferably a cyanate-based anion, because the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0042] Cyanate-based anions include anions having a cyano group, such as CNS - (Thiocyanate), (CN)2N - (dicyanate), B(CN)4 - , N.C.S. - , C(CN)3 - Examples include:
[0043] Among the cyanate anions, those containing 1 to 2 cyano groups are preferred, particularly (CN)N - or CNS - Preferably, (CN)N - is most preferred, because the composition has an even better balance of storage stability, electrical properties and adhesive strength.
[0044] Carboxylic acid anions include carboxylate anions (COO - , * is a bond). The number of carboxylate anions in one molecule of the carboxylate anion may be 1 or more, but is preferably 1 to 3, more preferably 1 to 2, and particularly preferably 1. This is because a better balance of storage stability, electrical properties, and adhesiveness is achieved. Carboxylic acid anions include *COO - is preferably an anion of a hydrocarbon carboxylic acid in which the anion is bonded to a hydrocarbon group, and more preferably an anion of an aliphatic carboxylic acid in which the carboxylate anion is bonded to an aliphatic hydrocarbon group. The composition has an excellent balance of storage stability, electrical properties, and adhesive strength. In the present disclosure, the carboxylate anion is preferably an anion of a monovalent aliphatic carboxylic acid. The carboxylate anion may be an anion of a hydrocarbon carboxylic acid in which one or more hydrogen atoms are substituted with halogen atoms. A specific example of a carboxylate anion is CHCOO - , C2H5COO - , C3H7COO - , C4H9COO - , C5H 11 COO - , C6H 13 COO - , C7H 15 COO - , C8H 17 COO - , C9H 19 COO - , C 10 H 21 COO - , C 11 H 23 COO - , (CH3)2CHCOO - , (CH3)3CCOO - , C6H5COO - , CF3COO - , C2F5COO - , C3F7COO - , C4F9COO - , C5F 11 COO - , C6F 13 COO - , C7F 15 COO - , C8F 17 COO - , C9F 19 COO - , C 10 F 21 COO - , C 11 F 23 COO - etc.
[0045] The number of carbon atoms in the carboxylate anion can be from 2 to 20, preferably from 2 to 10, more preferably from 2 to 5, particularly preferably from 2 to 3, and most preferably 2, i.e., the carboxylate anion is preferably an acetate anion, because this provides a better balance of storage stability, electrical properties, and adhesiveness. Acetate anions are acetate anions or anions in which one or more hydrogen atoms have been replaced by halogen atoms, such as CH3COO - , CF3COO - etc.
[0046] Halide ions include Cl - , Br - , I - etc.
[0047] The metal chloride anion is AlCl4. - , Al2Cl7 - etc.
[0048] Sulfonic acid anions include CH3SO3 - , CF3SO3 - , C4F9SO3 - , - O3S(CF2)3SO3 - Examples include:
[0049] The sulfonyl anion is (CF3SO2)3C - , ((CF3SO2)(CF3CO)N - or the following general formulas (α) to (δ): (α)(C n F 2n+1 SO2)2N - (wherein n is an integer from 1 to 10), (β)CF2(C m F 2m SO2)2N - (where m is an integer from 1 to 10), (γ) - O3S(CF2) l SO3- (wherein l is an integer from 1 to 10), (δ)(C p F 2p+1 SO2)N - (C q F 2q+1 SO2) (wherein p and q are integers of 1 to 10).
[0050] Other fluoride-based anions include BF4 - , PF6 - , AsF6 - , SbF6 - , NbF6 - , TaF6 - etc.
[0051] Examples of the ionic compound include compounds described as ionic liquids in JP 2020-007568 A. In addition, as a method for synthesizing an ionic compound, for example, the method described in JP 2020-007568 A can be used. Specific examples of the ionic compounds include 1-ethyl-3-methylimidazolium dicyanamide, 1-ethyl-3-methylimidazolium acetate, 1-ethyl-3-methylimidazolium trifluoroacetate, 1-butyl-3-methylimidazolium dicyanamide, 1-butyl-3-methylimidazolium trifluoroacetate, 1-butyl-3-methylimidazolium thiocyanate, 3-cyanopropylimidazolium dicyanamide, 1-allyl-3-methylimidazolium dicyanamide, 1-ethyl-3- Examples of such compounds include methylimidazolium ethyl sulfate, 1-ethyl-3-methylimidazolium methanesulfonate, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-ethyl-3-methylimidazolium dicyanamide, 1-ethyl-3-methylimidazolium dimethyl phosphate, 1-ethyl-3-methylimidazolium ethyl phosphate, and 1-ethyl-3-methylimidazolium methylphosphonate.
[0052] Commercially available ionic compounds include IL-P11, IL-P14, IL-IM1, IL-C1, IL-C3, IL-C5, IL-A1, IL-A2, IL-A3, IL-A4, IL-A5, IL-MA1, IL-MA2, IL-MA3, IL-OH1, IL-OH2, ILA21-9, and ILP14-2 manufactured by Koei Chemical Industry Co., Ltd., and AS-110 manufactured by Daiichi Kogyo Seiyaku Co., Ltd.
[0053] As the ionic compound, a combination of a nitrogen-containing aromatic heterocyclic cation and a cyanate-based anion, or a combination of a nitrogen-containing aromatic heterocyclic cation and an acetate-based anion can be preferably used, because the composition has an even better balance of storage stability, electrical properties, and adhesive strength.
[0054] The content of the ionic compound as the latent curing agent may be any content that can obtain the desired balance of storage stability, electrical properties, and adhesive strength, but is preferably 0.1 parts by mass or more and 30 parts by mass or less in the total of 100 parts by mass of the cyclic ether component and the ionic compound as the latent curing agent, more preferably 0.5 parts by mass or more and 20 parts by mass or less, particularly preferably 1 part by mass or more and 15 parts by mass or less, particularly preferably 2 parts by mass or more and 10 parts by mass or less, and most preferably 3 parts by mass or more and 8 parts by mass or less. This is because the composition has a better balance of storage stability, electrical properties, and adhesive strength. This is because the composition has particularly excellent adhesive strength.
[0055] The content of the ionic compound as the latent curing agent may be any content that provides a desired balance of storage stability, electrical properties, and adhesive strength, but is preferably 0.1 parts by mass or more and 15 parts by mass or less, more preferably 0.3 parts by mass or more and 10 parts by mass or less, particularly preferably 0.5 parts by mass or more and 5 parts by mass or less, and particularly preferably 0.8 parts by mass or more and 3 parts by mass or less, in a total of 100 parts by mass of the cyclic ether component, the ionic compound as the latent curing agent, and the elastomer component. This is because the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0056] The content of the ionic compound as the latent curing agent may be any content that provides a desired balance of storage stability, electrical properties, and adhesive strength, but is preferably 0.1 parts by mass or more and 15 parts by mass or less, more preferably 0.3 parts by mass or more and 5 parts by mass or less, particularly preferably 0.5 parts by mass or more and 4 parts by mass or less, and particularly preferably 0.8 parts by mass or more and 2 parts by mass or less, based on a total of 100 parts by mass of all components other than the solvent of the composition. This is because the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0057] The total content of the ionic compound as the latent curing agent, the cyclic ether component and the elastomer component is preferably 60 parts by mass or more, more preferably 65 parts by mass or more and 99 parts by mass or less, particularly preferably 70 parts by mass or more and 98 parts by mass or less, and particularly preferably 75 parts by mass or more and 98 parts by mass or less, in 100 parts by mass of all components other than the solvent of the composition. This is because the composition has a better balance of storage stability, electrical properties and adhesive strength.
[0058] 2. Cyclic ether component The cyclic ether component contains one or more compounds having a cyclic ether group (hereinafter, sometimes referred to as "cyclic ether compounds"). The cyclic ether group may be any group having at least one ether bond in a ring structure, and examples of such groups include an epoxy group, an oxetanyl group, etc. That is, as the cyclic ether component, one or more of epoxy compounds, oxetane compounds, etc. may be used in combination. In addition, compounds having a cyclic ether group and an ethylenically unsaturated group are included in the cyclic ether compounds. Examples of the ethylenically unsaturated group include an acryloyl group, a methacryloyl group, and a vinyl group. In addition, compounds having an alkoxysilyl group together with a cyclic ether group are generally classified as silane coupling agents, and do not fall under the above-mentioned cyclic ether compounds. For example, compounds having an alkoxysilyl group together with an epoxy group, such as γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropylmethyldiethoxysilane, and β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, are generally classified as silane coupling agents, and do not fall under the epoxy compounds. In addition, a compound having a cyclic ether group as an elastomer component is not considered to be a cyclic ether compound but is considered to be an elastomer component. Therefore, a rubber-modified epoxy compound described later is not considered to be an epoxy compound. Furthermore, "resins having a phenylene ether skeleton" described below as other resin components that have a cyclic ether group are not considered to be cyclic ether components such as epoxy compounds in the present disclosure. Therefore, even if a "resin having a phenylene ether skeleton" has an epoxy group, it does not fall under the category of an epoxy compound.
[0059] The type of cyclic ether group in the cyclic ether compound may be any one that provides a desired balance of storage stability, electrical properties, and adhesive strength, but it is preferable that the cyclic ether group is an epoxy group, i.e., the cyclic ether component contains an epoxy compound, because the composition has a better balance of storage stability, electrical properties, and adhesive strength due to the use of such a cyclic ether component.
[0060] (1) Epoxy compounds The epoxy compound includes all compounds containing an epoxy group. For example, a compound containing both an epoxy group and an oxetane group is considered to be an epoxy compound. Examples of such epoxy compounds include aromatic epoxy compounds, alicyclic epoxy compounds, and aliphatic epoxy compounds. In the present disclosure, the cyclic ether compound preferably contains at least one of an aromatic epoxy compound and an aliphatic epoxy compound, and more preferably contains at least one of an aromatic epoxy compound and an aliphatic epoxy compound containing an aliphatic ring (hereinafter, sometimes referred to as an aliphatic ring-containing epoxy compound), and particularly preferably contains an aromatic epoxy compound. This is because the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0061] (1-1) Aromatic epoxy compounds The aromatic epoxy compound has an aromatic ring and an epoxy group, but does not have a cycloalkene oxide structure. In addition, those having an aromatic ring and an aliphatic ring are also considered to be aromatic epoxy compounds. Here, examples of the aromatic ring include naphthalene, anthracene, phenanthrene, pyrene, etc. In the present disclosure, the aromatic ring is preferably a benzene ring, because the composition has particularly excellent electrical properties. Examples of such aromatic epoxy compounds include polyglycidyl ethers of polyhydric phenols having at least one aromatic ring or their alkylene oxide adducts. Examples of polyglycidyl ethers of polyhydric phenols or their alkylene oxide adducts include polyglycidyl ethers of bisphenol A, bisphenol F, or compounds obtained by adding alkylene oxides to these; epoxy novolac resins (phenol novolac type epoxy compounds); polyglycidyl ethers of aromatic compounds having two or more phenolic hydroxyl groups such as resorcinol, hydroquinone, and catechol; dicyclopentadiene type epoxy resins obtained by epoxidizing co-condensed resins of dicyclopentadiene and phenolic compounds; dicyclopentadiene modified epoxy resins which are polyglycidyl ethers of dicyclopentadiene modified phenolic resins; cyclopentadiene modified epoxy resins which are polyglycidyl ethers of cyclopentadiene modified phenolic resins. Other examples of the aromatic epoxy compound include polyglycidyl ethers of aromatic compounds having two or more alcoholic hydroxyl groups, such as benzenedimethanol, benzenediethanol, and benzenedibutanol; polyglycidyl esters of polybasic aromatic compounds having two or more carboxylic acids, such as phthalic acid, terephthalic acid, and trimellitic acid; glycidyl esters of benzoic acids, such as benzoic acid, toluic acid, and naphthoic acid; and epoxidized products of styrene oxide or divinylbenzene.
[0062] In the present disclosure, the aromatic epoxy compound is preferably a polyglycidyl ether of a polyhydric phenol having at least one aromatic ring or an alkylene oxide adduct thereof, for example, a compound represented by the following general formula (6-1) or (6-2), and among them, a compound represented by the above general formula (6-1) is preferable. This is because the composition has a better balance of storage stability, electrical properties, and adhesive strength. This is because the composition has particularly excellent electrical properties.
[0063] [ka] (In general formula (6-1), R 62-1 and R 63-1 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, r1 and s1 each independently represent a number from 0 to 5; R 61-1 represents a divalent aromatic ring-containing group represented by the following general formula (7):
[0064] [ka] (In general formula (7), R 71 , R 72 , R 73 , R 74 , R 75 , R 76 , R 77 , R 78 , R 79 , R 80 , R 81 , R 82 , R 83 , R 84 , R 85 , R 86 and R 87 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, Z 3 and Z 4 each independently represents a single bond or an alkylene group having 1 to 4 carbon atoms, and a hydrogen atom in the alkylene group may be substituted with a methyl group or a halogen atom; t represents an integer from 0 to 5; u represents an integer from 0 to 30; * indicates the site of attachment.)
[0065] [ka] In the general formula (6-2), L1 and L2 represent divalent hydrocarbon groups, and R 21 , R 22 and R 23 each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 4 carbon atoms; m1 , m 3 each independently represents a number from 0 to 4; m 2 represents a number from 0 to 3, and R 22 and m 2 When each of the groups is present in plural, they may be the same or different. 1 is a number greater than or equal to 0.)
[0066] R in general formula (6-1) 62-1 and R 63-1 As the alkyl group having 1 to 4 carbon atoms represented by the formula: 1 Examples of the alkyl group represented by the formula (I) include those having a specific number of carbon atoms among the groups listed above, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a s-butyl group, and a t-butyl group.
[0067] R in general formula (7) 71 , R 72 , R 73 , R 74 , R 75 , R 76 , R 77 , R 78 , R 79 , R 80 , R 81 , R 82 , R 83 , R 84 , R 85 , R 86 and R 87 Examples of the alkyl group having 1 to 4 carbon atoms represented by the formula (6-1) include R 62-1 and R 63-1 Examples of the alkyl group include the same groups as those of the alkyl group having 1 to 4 carbon atoms represented by the following formula:
[0068] Z in general formula (7) 3 and Z 4Examples of the alkylene group having 1 to 4 carbon atoms represented by the formula (I) include a methylene group, a methylidene group, an ethylene group, an ethylidene group, an n-propylene group, a propylidene group, an isopropylidene group, a methylethylene group, an n-butylene group, a butylidene group, an isobutylidene group, a sec-butylidene group, a 1,2-dimethylethylene group, a 1-methylpropylene group, and a 2-methylpropylene group.
[0069] Z in general formula (7) 3 and Z 4 Examples of the halogen atom substituting a hydrogen atom in the alkylene group having 1 to 4 carbon atoms represented by the following formula (1) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
[0070] In general formula (6-1), r1 and s1 are each preferably independently an integer of 0 to 3, more preferably an integer of 0 to 2, particularly preferably an integer of 0 to 1, and particularly preferably 0. This is because the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0071] In the general formula (7), R 71 , R 72 , R 73 , R 74 , R 75 , R 76 , R 77 , R 78 , R 79 , R 80 , R 81 , R 82 , R 83 , R 84 , R 85 , R 86 and R 87 is preferably a hydrogen atom or an alkyl group having 1 to 2 carbon atoms, i.e., a hydrogen atom, a methyl group, or an ethyl group, and is more preferably a hydrogen atom, because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0072] In the general formula (7), Z 3 and Z4 are each independently preferably an alkylene group having 1 to 4 carbon atoms, more preferably an alkylene group having 2 to 4 carbon atoms, and particularly preferably an alkylene group having 2 to 3 carbon atoms such as an ethylene group, an ethylidene group, a propylene group, a propylidene group, or an isopropylidene group, and particularly preferably an ethylidene group, an isopropylidene group, or the like, that is, the aromatic epoxy compound is a compound having a bisphenol structure such as a bisphenol A structure or a bisphenol F structure. This is because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0073] In general formula (7), t is preferably 0 to 3, and more preferably 0 to 1. Also, u is preferably 0 to 10, and more preferably 0 to 5, and particularly preferably 0 to 2, and more preferably 0. When t and u are within the above ranges, the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0074] Examples of the divalent hydrocarbon group represented by L1 and L2 in general formula (6-2) include aliphatic hydrocarbon groups and aromatic hydrocarbon ring-containing groups.
[0075] Examples of the aliphatic hydrocarbon group include linear or branched alkylene groups having 1 to 30 carbon atoms, and divalent groups containing an aliphatic ring having 3 to 30 carbon atoms. Examples of the linear or branched alkylene group having 1 to 30 carbon atoms include a methylene group, an ethylidene group, a propylidene group, and an isopropylidene group. The aliphatic ring may be a monocyclic structure or a condensed ring structure. The aliphatic ring may be any ring that does not have aromaticity, and may be a saturated aliphatic ring that does not have an unsaturated bond such as an unsaturated double bond as a bond that constitutes the ring, or an unsaturated aliphatic ring that has an unsaturated bond as a bond that constitutes the ring, such as cyclohexene. Examples of the aliphatic ring having a monocyclic structure include a cyclohexane ring, a cycloheptane ring, and a cyclodecane ring. Examples of the fused aliphatic ring, which is an aliphatic ring having a fused ring structure, include fused aliphatic hydrocarbon rings such as an adamantane ring, a bornane ring, a norbornane ring, a tricyclodecane ring, a tetracyclododecane ring, a decalin ring, a cyclopentadiene ring, a dicyclopentadiene ring, and a tetrahydrodicyclopentadiene ring. Divalent groups containing an aliphatic ring represented by L1 and L2 include aliphatic ring groups obtained by removing two hydrogen atoms from the aliphatic ring, and groups in which one or more hydrogen atoms of the aliphatic ring group are substituted with a substituent. Examples of the substituent include an alkylene group having 1 to 4 carbon atoms, and a group in which one or more methylene groups in the alkylene group are substituted with -O-, provided that the oxygen atoms are not adjacent to each other.
[0076] The aromatic hydrocarbon ring-containing group is a group that has an aromatic hydrocarbon ring. As the aromatic hydrocarbon ring-containing group, an aromatic hydrocarbon ring-containing group having 6 to 30 carbon atoms can be used. The aromatic hydrocarbon ring-containing group may have a monocyclic structure or a polycyclic structure. The polycyclic aromatic hydrocarbon ring-containing group may be a condensed ring structure or may have two linked aromatic hydrocarbon rings. The aromatic hydrocarbon ring-containing group in which two aromatic hydrocarbon rings are linked may be one in which two aromatic hydrocarbon rings of a monocyclic structure are linked, one in which an aromatic hydrocarbon ring of a monocyclic structure and an aromatic hydrocarbon ring of a fused ring structure are linked, or one in which an aromatic hydrocarbon ring of a fused ring structure and an aromatic hydrocarbon ring of a fused ring structure are linked. The linking group linking the two aromatic hydrocarbon rings may be any group that can impart aromaticity to the aromatic hydrocarbon ring-containing group as a whole, and examples of such a linking group include a single bond, a sulfide group (-S-), and a carbonyl group. Examples of the aromatic hydrocarbon ring having a monocyclic structure include benzene, toluene, ethylbenzene, and 2,4,6-trimethylbenzene. Examples of the aromatic hydrocarbon ring having a condensed ring structure include naphthalene, anthracene, phenanthrene, and pyrene. Examples of aromatic hydrocarbon ring-containing groups in which two aromatic hydrocarbon rings are linked include groups in which aromatic hydrocarbon rings having a monocyclic structure are linked, such as diphenyl sulfide and benzoylphenyl.
[0077] As the groups represented by L1 and L2 in the general formula (6-2), aromatic hydrocarbon ring-containing groups and divalent groups containing an aliphatic ring are preferred, and aromatic hydrocarbon ring-containing groups are particularly preferred. The composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0078] In the present disclosure, the aromatic hydrocarbon ring-containing group used in L1 and L2 is preferably an aromatic hydrocarbon ring-containing group having 8 to 20 carbon atoms, and more preferably an aromatic hydrocarbon ring-containing group having 10 to 15 carbon atoms, because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength. In the present disclosure, the aromatic hydrocarbon ring-containing group is preferably a polycyclic structure, and is preferably a group in which two aromatic hydrocarbon rings are linked, and is particularly preferably a group in which aromatic hydrocarbon rings of a monocyclic structure are linked, and is particularly preferably a group in which the linking group linking the aromatic hydrocarbon rings is a single bond, and is particularly preferably a biphenyl group-containing group. This is because the composition has a better balance of storage stability, electrical properties, and adhesive strength. In the present disclosure, the biphenyl group-containing group is preferably represented by formula (10).
[0079] [ka] (In general formula (10), R 121 , R 122 , R 123 , R 124 , R 125 , R 126 , R 127 , R 128each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 4 carbon atoms; R 130 , R 131 each independently represents a direct bond or an alkylene group having 1 to 4 carbon atoms.
[0080] R in Equation (10) 121 ~R 128 As the alkyl group and halogen atom represented by the formula (6-2), 61 The groups exemplified in the above formula (10) are the same as those exemplified in the above formula (10). 130 , R 131 The alkylene group represented by the formula (7) is Z 3 The same groups as those exemplified above are included.
[0081] R 121 ~R 128 is preferably a hydrogen atom or an alkyl group having 1 to 2 carbon atoms, and particularly preferably a hydrogen atom, because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength. R 130 , R 131 is preferably a direct bond or an alkylene group having 1 to 2 carbon atoms, and particularly preferably a methylene group, because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0082] In the present disclosure, the divalent group containing an aliphatic ring used for L1 and L2 is preferably a divalent group containing an aliphatic ring having 8 to 18 carbon atoms, particularly preferably a divalent group containing a fused aliphatic hydrocarbon ring having 8 to 18 carbon atoms, more particularly preferably a divalent group containing a fused saturated aliphatic hydrocarbon ring having 8 to 18 carbon atoms, and particularly preferably a group represented by the following general formula (9): This is because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0083] [ka] (In general formula (9), R110 and R 111 each independently represents a direct bond, an alkylene group having 1 to 4 carbon atoms, or the above alkylene group in which one or more methylene groups are substituted with -O- with no adjacent oxygen atoms, * indicates the site of attachment.)
[0084] When the groups represented by L1 and L2 in the general formula (6-2) are groups represented by the general formula (9), R 110 and R 111 is preferably a direct bond, since the composition has a better balance of storage stability, electrical properties and adhesive strength.
[0085] R in general formula (6-2) 21 , R 22 and R 23 Examples of the alkyl group having 1 to 4 carbon atoms represented by the formula (6-1) include R 62-1 and R 63-1 Examples of the alkyl group include the same groups as those of the alkyl group having 1 to 4 carbon atoms represented by the following formula:
[0086] In the general formula (6-2), m 1 and m 3 are each independently preferably an integer of 0 to 3, more preferably an integer of 0 to 2, particularly preferably an integer of 0 to 1, and particularly preferably 0. This is because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength. m 2 is preferably an integer of 0 to 2, more preferably an integer of 0 to 1, and particularly preferably 0. This is because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0087] In general formula (6-2), n1 is preferably in the range of 40 to 100° C., more preferably 45 to 90° C., and particularly preferably 50 to 80° C., such that the softening point as measured by the ring and ball method (JIS K5902) is in the range of 40 to 100° C., more preferably 45 to 90° C., and particularly preferably 50 to 80° C. This is because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0088] Examples of commercially available products that can be suitably used as the aromatic epoxy compound include those described in Japanese Patent No. 6103653 and the like.
[0089] The total content of the aromatic epoxy compound and the aliphatic epoxy compound may be any content that provides a desired balance of storage stability, electrical properties, and adhesive strength, and is preferably 50 parts by mass or more, more preferably 70 parts by mass or more, and even more preferably 90 parts by mass or more, in a total of 100 parts by mass of the epoxy compounds. By having the content within the above range, the composition has a better balance of storage stability, electrical properties, and adhesive strength. When the epoxy compound contains only an aromatic epoxy compound among the aromatic epoxy compound and the aliphatic epoxy compound, the preferred range of the content of the aromatic epoxy compound can be the same as the preferred range of the total content of the aromatic epoxy compound and the aliphatic epoxy compound. In addition, a preferred content of the total amount of the aromatic epoxy compound and the aliphatic epoxy compound containing an aliphatic ring in the epoxy compounds can be within the same range as the preferred ratio of the aromatic epoxy compound and the aliphatic epoxy compound in the total epoxy compounds.
[0090] (1-2) Aliphatic epoxy compounds The aliphatic epoxy resin has an epoxy group and does not contain a cycloalkene oxide structure or an aromatic ring. Examples of such aliphatic epoxy compounds include polyglycidyl ethers of aliphatic polyhydric alcohols or their alkylene oxide adducts; polyglycidyl esters of aliphatic long-chain polybasic acids; homopolymers synthesized by vinyl polymerization of glycidyl acrylate or glycidyl methacrylate; and copolymers synthesized by vinyl polymerization of glycidyl acrylate or glycidyl methacrylate with other vinyl monomers. Representative compounds include glycidyl ethers of polyhydric alcohols such as diglycidyl ethers of diols, triglycidyl ethers of glycerin, triglycidyl ethers of trimethylolpropane, tetraglycidyl ethers of sorbitol, and hexaglycidyl ethers of dipentaerythritol; polyglycidyl ethers of polyether polyols obtained by adding one or more alkylene oxides to aliphatic polyhydric alcohols such as propylene glycol, trimethylolpropane, and glycerin; and diglycidyl esters of aliphatic long-chain dibasic acids. Further examples include monoglycidyl ethers of higher aliphatic alcohols, monoglycidyl ethers of polyether alcohols obtained by adding alkylene oxides to phenol, cresol, butylphenol, or these, glycidyl esters of higher fatty acids, epoxidized soybean oil, epoxy octyl stearate, epoxy butyl stearate, and epoxidized polybutadiene. Further, the aliphatic epoxy compound may also be a hydrogenated product of an aromatic epoxy compound, such as hydrogenated bisphenol A diglycidyl ether. Examples of the aliphatic epoxy compound include compounds having a structure in which an oxiranyl group is directly bonded to a cycloalkyl ring derived from an epoxycycloalkyl ring via a single bond as a constituent unit, and having a structure in which epoxy groups of the epoxycycloalkyl ring are polymerized together as a main chain structure, such as a 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct of 2,2-bis(hydroxymethyl)-1-butanol.
[0091] As the aliphatic epoxy compound, any of aliphatic epoxy compounds containing an aliphatic ring such as an aliphatic hydrocarbon ring or an aliphatic heterocycle (hereinafter, sometimes referred to as an aliphatic ring-containing epoxy compound) and aliphatic epoxy compounds not having an aliphatic ring (hereinafter, sometimes referred to as a chain epoxy compound) is preferable, among which an aliphatic ring-containing epoxy compound is preferable, and an aliphatic hydrocarbon ring-containing epoxy compound having an aliphatic hydrocarbon ring is particularly preferable. By including the aliphatic epoxy compound, the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0092] The aliphatic hydrocarbon ring may be any ring in which the ring-forming atoms are only carbon atoms and which does not have aromaticity. Furthermore, the aliphatic hydrocarbon ring is not limited to an aliphatic hydrocarbon ring structure, but also includes a group in which one or more hydrogen atoms of an aliphatic hydrocarbon ring structure are substituted with a straight-chain or branched alkyl group. Examples of such an aliphatic hydrocarbon ring include a monocyclic aliphatic hydrocarbon ring such as a cyclohexane ring, and a polycyclic aliphatic hydrocarbon ring having a structure in which two or more monocyclic aliphatic hydrocarbon rings, such as an isobornyl ring, an adamantane ring, a dicyclopentene ring, a dicyclopentane ring, a tricyclodecane ring, a norbornene ring, and a norbornane ring, share one or more carbon atoms in the ring.
[0093] The aliphatic heterocycle may be any ring-forming atom that contains an atom other than a carbon atom and does not have aromaticity, and examples thereof include a pyrrolidine ring, a piperidine ring, a piperazine ring, a morpholine ring, a thiomorpholine ring, a homopiperidine ring, a homopiperazine ring, a tetrahydropyridine ring, a tetrahydroquinoline ring, a tetrahydroisoquinoline ring, a tetrahydrofuran ring, a tetrahydropyran ring, a dihydrobenzofuran ring, a tetrahydrocarbazole ring, a caprolactam ring, an isocyanuric ring, and a hydantoin ring.
[0094] The aliphatic hydrocarbon ring-containing epoxy compound is preferably a compound represented by the following general formula (6-3): By including such an aliphatic hydrocarbon ring-containing epoxy compound, the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0095] [ka] (In general formula (6-3), R 62-2 and R 63-2 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, r2 and s2 each independently represent a number from 0 to 5; R 61-2 represents the following general formula (8) or general formula (9).
[0096] [ka] (In general formula (8), R 91 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R 92 , R 93 , R 94 , R 95 , R 96 , R 97 , R 98 , R 99 , R 100 , R 101 , R 102 , R 103 , R 104 , R 105 , R 106 and R 107 each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 4 carbon atoms, Z 5 and Z 6 each independently represents a single bond, an alkylene group having 1 to 4 carbon atoms which may be linear, branched or cyclic, or a group in which one or more methylene groups in the alkylene group are substituted with -CO-O- or O-CO-, provided that no oxygen atoms are adjacent to each other; v and w each independently represent a number from 0 to 5; * indicates the site of attachment.)
[0097] R in general formula (6-3) 62-2 and R 63-2 Examples of the alkyl group having 1 to 4 carbon atoms represented by the formula (6-1) include R 62-1 and R 63-1 Examples of the alkyl group include the same groups as those of the alkyl group having 1 to 4 carbon atoms represented by the following formula:
[0098] R in general formula (8) 91 , R 92 ~R 107 Examples of the alkyl group having 1 to 4 carbon atoms represented by the formula (6-1) include R 62 and R 63 Examples of the alkyl group include the same groups as those of the alkyl group having 1 to 4 carbon atoms represented by the following formula:
[0099] R in general formula (8) 92 ~R 107 Examples of halogen atoms represented by the formula (7) include Z 3 and Z 4 Examples of the halogen atom include the same atoms as those replacing the hydrogen atoms in the alkylene group having 1 to 4 carbon atoms represented by the following formula:
[0100] Z in general formula (8) 5 and Z 6 As the alkylene group having 1 to 4 carbon atoms represented by the formula (7), Z 3 and Z 4 Examples of the alkylene group include the alkylene group having 1 to 4 carbon atoms represented by the following formula:
[0101] The general formula (9) can be the same as that used in the above general formula (6-2).
[0102] In general formula (6-3), R 61-2 is preferably a group represented by general formula (8), because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0103] In general formula (6-3), r2 and s2 are each preferably independently an integer of 0 to 3, more preferably an integer of 0 to 2, particularly preferably an integer of 0 to 1, and most preferably 0. This is because the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0104] In the general formula (8), R 92 ~R 107 is preferably a hydrogen atom or an alkyl group having 1 to 2 carbon atoms, i.e., a hydrogen atom, a methyl group, or an ethyl group, and is more preferably a hydrogen atom, because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0105] In the general formula (8), Z 5 and Z 6 are each independently preferably an alkylene group having 1 to 4 carbon atoms, more preferably an alkylene group having 2 to 4 carbon atoms, and particularly preferably an alkylene group having 2 to 3 carbon atoms such as an ethylene group, an ethylidene group, a propylene group, a propylidene group, or an isopropylidene group, and particularly preferably an ethylidene group, an isopropylidene group, or the like, that is, the aliphatic epoxy compound is preferably a compound having a hydrogenated bisphenol structure such as a hydrogenated bisphenol A structure or a hydrogenated bisphenol F structure. This is because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0106] In general formula (8), v is preferably 0 to 3, and more preferably 0 to 1. Furthermore, w is preferably 0 to 3, and more preferably 0 to 1, and particularly preferably 0. By setting v and w within the above ranges, the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0107] Examples of commercially available products that can be suitably used as the above aliphatic epoxy compound include those described in Japanese Patent No. 6103653 and the like.
[0108] (1-3) Alicyclic epoxy compounds The alicyclic epoxy compound is a compound having a cycloalkene oxide structure. The cycloalkene oxide structure is a structure in which an aliphatic ring and an epoxy ring share a part of a ring structure, such as a cyclohexene oxide structure or a cyclopentene oxide structure obtained by epoxidizing a cyclohexene ring-containing compound or a cyclopentene ring-containing compound with an oxidizing agent. In addition, a group obtained by removing one hydrogen atom from the cycloalkane of such a cycloalkene oxide structure may be called an "epoxy cycloalkyl group".
[0109] More specifically, the alicyclic epoxy compound may be 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1-methylhexanecarboxylate, 6-methyl-3,4-epoxycyclohexylmethyl-6-methyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-3-methylcyclohexylmethyl-3,4-epoxy-3-methylcyclohexanecarboxylate, 3,4-epoxy-5-methylcyclohexylmethyl-3,4-epoxy-5-methylcyclohexanecarboxylate, 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4- Examples of the epoxy cyclohexane-metadioxane include bis(3,4-epoxycyclohexylmethyl)adipate, 3,4-epoxy-6-methylcyclohexylcarboxylate, methylene bis(3,4-epoxycyclohexane), dicyclopentadiene diepoxide, ethylene bis(3,4-epoxycyclohexanecarboxylate), dioctyl epoxyhexahydrophthalate, di-2-ethylhexyl epoxyhexahydrophthalate, 1-epoxyethyl-3,4-epoxycyclohexane, 1,2-epoxy-2-epoxyethylcyclohexane, 3,4-epoxycyclohexylmethyl acrylate, and 3,4-epoxycyclohexylmethyl methacrylate.
[0110] In the present disclosure, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate and 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1-methylhexanecarboxylate are preferred, because the compositions have a better balance of storage stability, electrical properties, and adhesive strength.
[0111] Examples of commercially available products that can be suitably used as the alicyclic epoxy compound include those described in Japanese Patent No. 6103653 and the like.
[0112] (1-4)Other The content of the epoxy compound may be any content that provides a desired balance of storage stability, electrical properties, and adhesive strength, but for example, it is preferably 60 parts by mass or more, more preferably 90 parts by mass or more, particularly preferably 95 parts by mass or more, and particularly preferably 100 parts by mass, that is, it is preferable that the cyclic ether component contains only the epoxy compound. By having the content within the above range, the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0113] (2) Oxetane compounds The oxetane compound is a compound having an oxetane ring but not an epoxy group. Examples of such oxetane compounds include 3-ethyl-3-hydroxymethyloxetane, 3-(meth)allyloxymethyl-3-ethyloxetane, (3-ethyl-3-oxetanylmethoxy)methylbenzene, 4-fluoro-[1-(3-ethyl-3-oxetanylmethoxy)methyl]benzene, 4-methoxy-[1-(3-ethyl-3-oxetanylmethoxy)methyl]benzene, [1-(3-ethyl-3-oxetanylmethoxy)ethyl]phenyl ether, isobutoxymethyl(3-ethyl-3-oxetanylmethyl)ether, Isobornyloxyethyl (3-ethyl-3-oxetanylmethyl) ether, isobornyl (3-ethyl-3-oxetanylmethyl) ether, 2-ethylhexyl (3-ethyl-3-oxetanylmethyl) ether, ethyl diethylene glycol (3-ethyl-3-oxetanylmethyl) ether, dicyclopentadiene (3-ethyl-3-oxetanylmethyl) ether, dicyclopentenyloxyethyl (3-ethyl-3-oxetanylmethyl) ether, dicyclopentenyl (3-ethyl-3-oxetanylmethyl) ether, tetrahydrofuran Drofurfuryl (3-ethyl-3-oxetanylmethyl) ether, tetrabromophenyl (3-ethyl-3-oxetanylmethyl) ether, 2-tetrabromophenoxyethyl (3-ethyl-3-oxetanylmethyl) ether, tribromophenyl (3-ethyl-3-oxetanylmethyl) ether, 2-tribromophenoxyethyl (3-ethyl-3-oxetanylmethyl) ether, 2-hydroxyethyl (3-ethyl-3-oxetanylmethyl) ether, 2-hydroxypropyl (3-ethyl-3-oxetanylmethyl) ether, Butoxyethyl (3-ethyl-3-oxetanylmethyl) ether, pentachlorophenyl (3-ethyl-3-oxetanylmethyl) ether, pentabromophenyl (3-ethyl-3-oxetanylmethyl) ether, bornyl (3-ethyl-3-oxetanylmethyl) ether, 3,7-bis(3-oxetanyl)-5-oxa-nonane, 3,3'-(1,3-(2-methyleneyl)propanediylbis(oxymethylene))bis-(3-ethyloxetane), 1,4-bis[(3-ethyl-3-oxetanylmethoxy)methyl]benzene, 1,2-bis[(3-ethyl-3-oxetanylmethoxy)methyl]ethane, 1,3-bis[(3-ethyl-3-oxetanylmethoxy)methyl]propane, ethylene glycol bis(3-ethyl-3-oxetanylmethyl)ether, dicyclopentenyl bis(3-ethyl-3-oxetanylmethyl)ether, triethylene glycol bis(3-ethyl-3-oxetanylmethyl)ether, tetraethylene glycol bis(3-ethyl-3-oxetanylmethyl)ether, tricyclodecanediyldimethylene(3 -ethyl-3-oxetanylmethyl) ether, trimethylolpropane tris(3-ethyl-3-oxetanylmethyl) ether, 1,4-bis(3-ethyl-3-oxetanylmethoxy)butane, 1,6-bis(3-ethyl-3-oxetanylmethoxy)hexane, pentaerythritol tris(3-ethyl-3-oxetanylmethyl) ether, pentaerythritol tetrakis(3-ethyl-3-oxetanylmethyl) ether, polyethylene glycol bis(3-ethyl-3-oxetanylmethyl) ether , dipentaerythritol hexakis(3-ethyl-3-oxetanylmethyl) ether, dipentaerythritol pentakis(3-ethyl-3-oxetanylmethyl) ether, dipentaerythritol tetrakis(3-ethyl-3-oxetanylmethyl) ether, caprolactone-modified dipentaerythritol hexakis(3-ethyl-3-oxetanylmethyl) ether, caprolactone-modified dipentaerythritol pentakis(3-ethyl-3-oxetanylmethyl) ether, ditrimethylolpropane Examples of the bisphenol A bis(3-ethyl-3-oxetanylmethyl)ether include tetrakis(3-ethyl-3-oxetanylmethyl)ether, EO modified bisphenol A bis(3-ethyl-3-oxetanylmethyl)ether, PO modified bisphenol A bis(3-ethyl-3-oxetanylmethyl)ether, EO modified hydrogenated bisphenol A bis(3-ethyl-3-oxetanylmethyl)ether, PO modified hydrogenated bisphenol A bis(3-ethyl-3-oxetanylmethyl)ether, and EO modified bisphenol F(3-ethyl-3-oxetanylmethyl)ether.
[0114] (3)Other The content of the cyclic ether component may be any content that provides a desired balance of storage stability, electrical properties, and adhesive strength, and is preferably 1 part by mass or more and 60 parts by mass or less, more preferably 3 parts by mass or more and 40 parts by mass or less, particularly preferably 5 parts by mass or more and 35 parts by mass or less, and particularly preferably 10 parts by mass or more and 30 parts by mass or less, per 100 parts by mass of the cyclic ether component, the ionic compound as the latent curing agent, and the elastomer in the composition. By having the content within the above range, the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0115] The content of the cyclic ether component may be any content that can obtain a desired balance of storage stability, electrical properties, and adhesive strength, and is preferably 1 part by mass or more and 60 parts by mass or less, more preferably 3 parts by mass or more and 40 parts by mass or less, particularly preferably 5 parts by mass or more and 30 parts by mass or less, and particularly preferably 8 parts by mass or more and 25 parts by mass or less, in a total of 100 parts by mass of the components other than the solvent of the composition. By having the content within the above range, the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0116] 3. Elastomer component The elastomer is contained as a component other than the above-mentioned ionic compound and cyclic ether component. In addition, a compound having an elastomer component and a cyclic ether group such as an epoxy group, such as a rubber-modified epoxy compound, is considered to be an elastomer component.
[0117] (1) Types of elastomers An elastomer generally refers to an amorphous, soft polymeric substance that exhibits rubber elastic properties at room temperature. In the present disclosure, the elastomer is preferably one that can be plasticized (fluidized) by the application of heat and used for molding or processing, that is, a thermoplastic elastomer. The composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0118] Known thermoplastic elastomers include styrene-based elastomers, olefin-based elastomers, urethane-based elastomers, polyester-based elastomers, polyamide-based elastomers, acrylic-based elastomers, silicone-based elastomers, rubber-modified epoxy compounds, etc. In the present disclosure, one or more of the above may be used in combination. Among them, in the present disclosure, a polymer having a structural unit having an aromatic ring in a side chain is preferred, and a styrene-based elastomer is particularly preferred, because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength. The aromatic ring may be the same as that used in an aromatic epoxy compound. The main chain refers to the relatively longest bonded chain in a polymeric substance, and the side chain refers to a portion branched off from the main chain. Therefore, a structural unit having an aromatic ring in its side chain refers to a structure in which the aromatic ring is bonded to a bonded chain constituting the main chain.
[0119] The styrene-based elastomer may be a polymer having a structural unit derived from styrene or a derivative thereof, preferably a copolymer having a structural unit derived from styrene or a derivative thereof, and particularly preferably a copolymer having a structural unit derived from styrene or a derivative thereof (hereinafter also referred to as a "styrene unit") and a structural unit derived from an olefin (hereinafter also referred to as an "olefin unit"), because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0120] Examples of styrene or its derivatives include styrene, and compounds in which one or more hydrogen atoms in the benzene ring or α-position of styrene are substituted with an alkyl group having 1 to 6 carbon atoms, such as α-methylstyrene, 3-methylstyrene, 4-propylstyrene, and 4-cyclohexylstyrene. As styrene or its derivatives, styrene or α-methylstyrene is preferred. This is because the composition has a better balance of storage stability, electrical properties, and adhesive strength. When the styrene-based elastomer is a copolymer, it may be a random copolymer or a block copolymer.
[0121] When the styrene-based elastomer is a block copolymer having a styrene unit and an olefin unit, the styrene-based elastomer is preferably a copolymer in which one or more blocks consisting of olefin units (hereinafter also referred to as "olefin blocks") and one or more blocks consisting of one or more styrene units (hereinafter also referred to as "styrene blocks") are arranged. One olefin block is composed of a plurality of olefin units, and one styrene block is composed of a plurality of styrene units. Examples of units derived from olefin include divalent groups obtained by removing two hydrogen atoms from ethane, ethylene, propylene, butane, butylene, butadiene, hydrogenated butadiene, isoprene, hydrogenated isoprene, or other α-olefins. When the styrene-based elastomer is a block copolymer having a styrene unit and an olefin unit, the styrene unit and the olefin unit preferably account for 50% by mass or more in total, more preferably 80% by mass or more, in the styrene-based elastomer. The composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0122] Specific examples of styrene-based elastomers include block copolymers such as acrylonitrile-butadiene-styrene (ABS) resin, methyl methacrylate-butadiene-styrene (MBS) resin, heat-resistant ABS resin, styrene-butadiene-styrene (SBS) resin, styrene-isoprene-styrene (SIS) resin, styrene-butadiene-butylene-styrene (SBBS) resin, and methyl methacrylate-acrylonitrile-butadiene-styrene (MABS) resin, as well as hydrogenated styrene-based elastomer resins such as styrene-ethylene-butylene-styrene (SEBS) resin, styrene-ethylene-propylene-styrene (SEPS) resin, styrene-ethylene-propylene (SEP) resin, and styrene-ethylene-ethylene-propylene-styrene (SEEPS) resin, which are obtained by hydrogenating the double bonds of these butadienes or isoprenes. These can be used alone or in a mixture of multiple resins. SBS may be referred to as "polystyrene-polybutadiene", SEBS may be referred to as "polystyrene-poly(ethylene / butylene)block-polystyrene", SEPS may be referred to as "(polystyrene-poly(ethylene / propylene)block-polystyrene)", SEEPS may be referred to as "(polystyrene-poly(ethylene-ethylene / propylene)block-polystyrene)", and SBBS may be referred to as "(polystyrene-poly(butadiene-butylene)block-polystyrene)". In the present disclosure, among them, SBS, SEBS, SEPS, and SEEPS are preferred, and SEBS is most preferred. This is because the above composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0123] Examples of olefin-based elastomers include copolymers of α-olefins having 2 to 20 carbon atoms, such as ethylene, propylene, and 1-butene. Also included are copolymers of α-olefins and non-conjugated dienes having 2 to 20 carbon atoms, such as dicyclopentadiene, and carboxy-modified NBR obtained by copolymerizing butadiene-acrylonitrile copolymer with methacrylic acid. Examples of urethane-based elastomers include elastomers composed of structural units of a hard segment composed of low molecular weight ethylene glycol and diisocyanate, and a soft segment composed of a high molecular weight (long chain) diol and diisocyanate. The polyester-based elastomer may be an elastomer obtained by polycondensation of a dicarboxylic acid or a derivative thereof with a diol compound or a derivative thereof. Examples of polyamide-based elastomers include polyether block amide type elastomers and polyether ester block amide type elastomers, which use polyamide in the hard phase and polyether or polyester in the soft phase. Examples of the acrylic elastomer include an acrylonitrile-butyl acrylate copolymer, an acrylonitrile-butyl acrylate-ethyl acrylate copolymer, and an acrylonitrile-butyl acrylate-glycidyl methacrylate copolymer. Silicone-based elastomers contain organopolysiloxane as a main component, and examples thereof include polydimethylsiloxane, polymethylphenylsiloxane, and polydiphenylsiloxane. Examples of rubber-modified epoxy compounds include epoxy compounds of epoxidized butadiene-styrene copolymers, polydimethylsiloxane, etc. Compounds obtained by modifying a part or all of the epoxy groups of the various epoxy compounds listed in the above "2. Cyclic ether component" with butadiene-acrylonitrile rubber modified at both ends with carboxylic acid, terminal amino-modified silicone rubber, etc. can also be used.
[0124] (2) Styrene content When the elastomer in the present disclosure is a styrene-based elastomer, the content of the styrene unit in the styrene-based elastomer is preferably 30% by mass or more and 90% by mass or less, more preferably 40% by mass or more and 80% by mass or less, particularly preferably 45% by mass or more and 75% by mass or less, and particularly preferably 50% by mass or more and 70% by mass or less, because the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0125] (3) Physical properties (3-1) Physical property 1: MFR When the elastomer is SBS, the MFR of the SBS measured at 200° C. under a load of 5 kgf is preferably 1 g / 10 min to 20 g / 10 min, more preferably 2 g / 10 min to 10 g / 10 min, because the composition has a better balance of storage stability, electrical properties, and adhesive strength. Furthermore, when the elastomer is SEBS, the MFR (2.16 kg) of SEBS is preferably 0.5 g / 10 min to 15 g / 10 min, more preferably 1.0 g / 10 min to 10 g / 10 min, and particularly preferably 1.5 g / 10 min to 5 g / 10 min, because the composition has a better balance of storage stability, electrical properties, and adhesive strength. MFR is measured in accordance with ISO1133.
[0126] (3-2) Physical property 2: Density / specific gravity The density of the elastomer is 0.9 g / cm 3 More than 1.5g / cm 3 It is preferable that the density is 0.95 g / cm or less. 3 More than 1.2g / cm 3 More preferably, it is 0.96 g / cm or less. 3 More than 1.0g / cm 3 It is particularly preferable that the specific gravity of the elastomer is not more than 100 g / cm because the composition has a better balance of storage stability, electrical properties, and adhesive strength. 3 The density and specific gravity of elastomers can be measured in accordance with ISO 1183.
[0127] (4) Commercially available products Suitable elastomers include, for example: Tufprene (registered trademark) series: A, 125, 126S (styrene content 40%), Asaprene (registered trademark) series: T-411, T-432, T-437 (styrene content 30%), T-438 (styrene content 35%), T-439 (styrene content 45%), (all SBS), Tuftec (registered trademark) H series: H1221 (styrene content 12%), H1062, H1521 (styrene content 18%), H1052 (styrene content 20%), H1053 (styrene content 29%), H1 051 (42%), H1517 (43%), H1043 (67%) (all SEBS), Tuftech P series: P1083 (20%), P1500 (30%), P5051 (47%), P2000 (50%) (all SBBS), Tuftech M series: M1943 (20%), M1913, M1911, MP10 (30%) (all modified SEBS) (all manufactured by Asahi Chemical Industry Co., Ltd.); Elastomer AR series (SEBS, manufactured by Aronkasei Co., Ltd.); Kraton D Series: D0243, D0246, D1101, D1102, D1116, D1118, D1152, D1155, D1184, D1189, D1191, D1192, D4150, D4153, D4270, DX1000 (all SBS), D1111, D1113, D1114, D1117, D1119, D1124, D1126, D1161, D1162, D1163, D1164, D1170, D1171, D1173, D1183, D1193 (all SIS), Kraton G Series: A1535, A1536, G1633, G1640, G1641, G1642, G1643, G1645, G1650, G1651, G1652, G1654, G1657, G1660, G1701, G1702, G1726, G1730, G1740, G1765, G2705, G2708, G2806, G2832, G2836, G2874, G4609, G4610, G7705, G7720, G7723, G7820 (SEBS or SEPS) (all manufactured by Kraton Polymer Japan Co., Ltd.); TR series: TR2000 (40%), TR2001 (40%), TR2003 (43%), TR2250 (52%), 2500 (35%), TR2601 (30%), TR2787 (30%), TR2827 (24%), TR2086 (45%) (all SBS); SIS series: SIS5002 (22%), SIS5229 (15%), SIS5250 (20%), SIS5403 (15%), SIS5506 (16%) (all SIS); Dynaron (registered trademark) series: 8600P (15%), 8300P (9%), 8903P (35%), 9901P (all SEBS) (all manufactured by JSR Corporation); Denka STR (SBS, manufactured by Denki Kagaku Kogyo Co., Ltd.); Quintac (registered trademark) series: 3421 (14%), 3450 (19%), 3270 (24%), 3280 (25%), 3190 (30%), 3390 (48%), 3620 (14%), 3433N (16.5%), 3520 (15%) (all SIS), Zeofit series: ZFT1330 (SBS, 30%) (all Zeon Corporation); TPE-SB series (SEBS, manufactured by Sumitomo Chemical Co., Ltd.); Labaron® series (SEBS, manufactured by Mitsubishi Chemical Corporation); SEPTON (registered trademark) series: 1020 (SEP, 36%), 2002 (30%), 2004F (18%), 2005 (20%), 2006 (35%), 2063 (13%), 2104 (65%), (all SEPS), 4033 (30%), 4044 (32%), 4055 (30%), 4077 (30%), 4099 (30%) (all S EEPS), 8004 (31%), 8006 (33%), 8007L (30%), (all SEBS), HG252 (28%, SEEPS-OH), Hybra (registered trademark) series: 5125 (20%), 5127 (20%) (all SIS), 7125F (20%, SEPS), 7311F (12%, SEEPS) (all manufactured by Kuraray Co., Ltd.); Leostomer, Actimer (both manufactured by RIKEN TECHNOS CORPORATION), etc.
[0128] (5) Elastomer content In the total of 100 parts by mass of the elastomer, the cyclic ether component, and the ionic compound as the latent curing agent, the elastomer is 30 parts by mass or more. As a result, the composition of the present disclosure has excellent adhesive strength, electrical properties such as dielectric tangent, and solution stability. If the amount of elastomer is less than 30 parts by mass, the amount of epoxy increases accordingly, and the content of the ionic compound as the curing agent also increases in proportion thereto. Since the ionic compound has excellent electrical conductivity, if the amount added is too large, the electrical properties may decrease. It is preferable to set the amount of elastomer to a predetermined amount or less, because it is possible to more reliably prevent the adhesive strength from decreasing. From these viewpoints, in the total of 100 parts by mass of the elastomer, the cyclic ether component, and the ionic compound as the latent curing agent, the content of the elastomer is preferably 40 parts by mass or more and 95 parts by mass or less, particularly preferably 60 parts by mass or more and 93 parts by mass or less, and particularly preferably 70 parts by mass or more and 90 parts by mass or less. This is because the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0129] From the same viewpoint as above, the content of the elastomer is preferably 25 parts by mass or more and 95 parts by mass or less, more preferably 30 parts by mass or more and 90 parts by mass or less, even more preferably 40 parts by mass or more and 80 parts by mass or less, and particularly preferably 50 parts by mass or more and 70 parts by mass or less, based on 100 parts by mass of the total components other than the solvent of the composition. This is because the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0130] 4. Resin components other than cyclic ether components and elastomers (1) Type The composition may contain resin components other than the cyclic ether component and the elastomer (hereinafter also referred to as "other resin components"). The other resin components may be any resin that provides a desired balance of storage stability, electrical properties, and adhesive strength, but a resin having an aromatic ring in the main chain is preferred, and in particular, a resin having a phenylene ether skeleton is preferred, because the composition has a better balance of storage stability, electrical properties, and adhesive strength. Here, the phenylene ether skeleton refers to one having a structure represented by the following (X) as a structural unit constituting the main chain of a polymer.
[0131] [ka] (In the formula, * represents a bonding site.)
[0132] As the resin having a phenylene ether skeleton, those having various reactive groups such as those having a hydroxyl group at the terminal, those having a glycidyl ether group, and those having an ethylenically unsaturated group such as an acrylate group or a vinyl group can be used, but among them, those having an ethylenically unsaturated group at the terminal can be preferably used, and among them, those having a styrene group at the terminal are preferable, and specifically, those represented by the following general formula (2) are particularly preferable. This is because the composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0133] [ka] (In the general formula (2), -(OXO)- is represented by the following general formula (a). -(YO)- is represented by the following general formula (b). A plurality of Y's may be the same or different. n2 and n3 each represent an integer of 0 to 100, with at least one of them not being 0.)
[0134] [ka] (In general formula (a), R 11 , R 12 , R 13 , R 14 , R 15, R 16 , R 17 , R 18 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. L3 is a direct bond or a divalent organic group.
[0135] [ka] (In general formula (b), R 27 , R 28 are each independently an alkyl group having 1 to 6 carbon atoms or a phenyl group. 29 , R 30 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.
[0136] R in general formula (a) 11 ~R 18 and R in general formula (b) 27 ~R 30 As the alkyl group having 1 to 6 carbon atoms represented by the formula (1), 1 Examples of the alkyl group represented by the formula (I) include those having a specific number of carbon atoms among the groups listed above, and an alkyl group having 1 to 3 carbon atoms is preferred. The composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0137] Examples of the divalent organic group represented by L3 in general formula (b) include those having 1 to 12 carbon atoms, such as alkylidene groups such as methylene, ethylidene, 1-methylethylidene, and 1,1-propylidene, 1,4-phenylenebis(1-methylethylidene), 1,3-phenylenebis(1-methylethylidene), cyclohexylidene, phenylmethylene, naphthylmethylene, and 1-phenylethylidene.
[0138] The compound represented by the general formula (2) is a compound represented by the general formula (a) in which X is R 11 ,R 12 , R 13 , R 16 , R 17 , R 18is an alkyl group having 1 to 3 carbon atoms, and R 14 , R 15 is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 11 , R 12 , R 13 , R 16 , R 17 , R 18 is an alkyl group having 1 to 3 carbon atoms, and R 14 , R 15 is particularly preferably a hydrogen atom, and R 11 , R 12 , R 13 , R 16 , R 17 , R 18 is a methyl group, and R 14 , R 15 is particularly preferably a hydrogen atom, since the composition has an excellent balance of storage stability, electrical properties and adhesive strength.
[0139] L3 in general formula (b) is preferably a direct bond or an alkylidene group having 1 to 12 carbon atoms, more preferably a direct bond or an alkylidene group having 1 to 5 carbon atoms, and most preferably a direct bond, because the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0140] Y in the general formula (b) is R 27 , R 28 is an alkyl group having 1 to 3 carbon atoms, and R 29 , R 30 is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 27 , R 28 is a methyl group, and R 29 , R 30 is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 27 , R 28 is a methyl group, and R 29 , R 30 is most preferably a hydrogen atom, since the composition has an excellent balance of storage stability, electrical properties and adhesive strength.
[0141] Commercially available resins having a phenylene ether skeleton include, for example, the OPE (bifunctional polyphenylene ether oligomer) series, such as OPE-2Gly, OPE-2St, and OPE-2EA manufactured by Mitsubishi Gas Chemical Co., Ltd., and Noryl PPO640, SA120, SA90, and SA9000 manufactured by SABIC Japan, LLC.
[0142] The number average molecular weight of the other resin components is preferably 500 to 3,000, more preferably 800 to 2,000, and most preferably 1,000 to 1,500. This is because the composition has a better balance of storage stability, electrical properties, and adhesive strength. The number average molecular weight of the other resin components is the molecular weight calculated as polystyrene by GPC.
[0143] (2) Preferred content When the composition contains the other resin components, the amount of the other resin components is preferably 3 parts by mass or more and 75 parts by mass or less, more preferably 5 parts by mass or more and 50 parts by mass or less, still more preferably 15 parts by mass or more and 40 parts by mass or less, and particularly preferably 20 parts by mass or more and 30 parts by mass or less, relative to 100 parts by mass in total of the cyclic ether component, the elastomer, and the ionic compound as the latent curing agent, because the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0144] The amount of the other resin components is preferably 5 parts by mass or more and 50 parts by mass or less, more preferably 10 parts by mass or more and 40 parts by mass or less, and particularly preferably 15 parts by mass or more and 30 parts by mass or less, based on 100 parts by mass of the total content of the components other than the solvent in the composition of the present disclosure, because the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0145] 5. Other hardeners The composition may contain a curing agent other than the ionic compound as a latent curing agent (hereinafter, may be simply referred to as other curing agent).
[0146] The other curing agents include thermal curing agents, specifically phenolic resins, polyamines, latent curing agents (hereinafter, may be referred to as latent curing agent 2 to distinguish them from ionic compounds), and acid anhydrides. Examples of the latent curing agent 2 include a dicyandiamide type latent curing agent, an imidazole type latent curing agent, and a polyamine type latent curing agent. As such other curing agents, for example, those described in JP 2019-038891 A can be used. The other curing agent preferably contains a latent curing agent, and in particular, it is preferable to contain a dicyandiamide type latent curing agent, an imidazole type latent curing agent, etc. The composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0147] The dicyandiamide-type latent curing agent may be dicyandiamide alone or, if necessary, in combination with an epoxy resin curing accelerator described below. Commercially available dicyandiamide-type latent curing agents include Omicure DDA-5 manufactured by PTI Japan Co., Ltd., and DICY7, DICY15, and DICY50 manufactured by Mitsubishi Chemical Corporation.
[0148] Examples of the imidazole-type latent curing agent include an imidazole compound and an epoxy adduct-type imidazole compound which is a reaction product of an imidazole compound and an epoxy compound.
[0149] The imidazole compound used as the imidazole-type latent curing agent is one that does not have a structure obtained by reacting an imidazole structure with an epoxy structure, and examples thereof include 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, 2,4-diamino-6-[2'-ethyl-4'-methylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine, and 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine. imidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine isocyanuric acid adduct, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-phenylimidazolium trimellitate, 1-cyanoethyl-2-undecylimidazole, and 2,4-diamino-6-[2'-undecylimidazolyl-(1')]-ethyl-s-triazine. In addition, the imidazole compound used in the production of an epoxy adduct type imidazole compound described later can also be used as an imidazole type latent curing agent.
[0150] As the imidazole-type latent curing agent, one of the imidazole compounds may be used alone, or two or more of them may be used in combination.
[0151] Commercially available imidazole compounds used as the imidazole-type latent curing agent include 2P4MHZ-PW (2-phenyl-4-methyl-5-hydroxymethylimidazole), 2PHZ-PW (2-phenyl-4,5-dihydroxymethylimidazole), C11Z (2-undecylimidazole), C11Z-CN (1-cyanoethyl-2-undecylimidazole), C17Z (2-heptadecylimidazole), and 2E4MZ-CN (1-cyanoethyl-2-ethyl-4-methylimidazole). , 2PZ-CN (1-cyanoethyl-2-phenylimidazole), 2MZ-A (2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine), 2E4MZ-A (2,4-diamino-6-[2'-ethyl-4'methylimidazolyl-(1')]-ethyl-s-triazine), and 2MAOK-PW (2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine isocyanuric acid adduct) (all of which are product names manufactured by Shikoku Chemical Industry Co., Ltd.).
[0152] Examples of the imidazole compound used in the production of the epoxy adduct type imidazole compound include 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, and 2-phenylimidazole. Examples of the epoxy compound used in the production of the epoxy adduct type imidazole compound include the compounds exemplified in the section "(1) Epoxy compound" of "2. Cyclic ether component" described below.
[0153] Commercially available imidazole-type latent hardeners include ADEKA HARDENER EH-5011S, ADEKA HARDENER EH-5046S, etc. These can be used alone or as a suitable mixture.
[0154] The content of the other curing agent may be any content that provides a desired balance of storage stability, electrical properties, and adhesive strength, but is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, particularly preferably 3 parts by mass or less, and particularly preferably 1 part by mass or less, relative to 100 parts by mass of the ionic compound as the latent curing agent. This is because the composition has a better balance of storage stability, electrical properties, and adhesive strength.
[0155] 6. Solvent The composition may contain a solvent, if necessary. The above-mentioned solvent is liquid at room temperature (25°C) and atmospheric pressure, capable of dispersing or dissolving each component in the composition, and does not react with each other or with each component such as the cyclic ether component, the latent curing agent, the elastomer component, other curing agents, etc. Therefore, cyclic ether components, latent curing agents, elastomer components, other curing agents, etc. are not included in the solvent even if they are liquid at room temperature (25° C.) and atmospheric pressure.
[0156] As such a solvent, either water or an organic solvent can be used, but an organic solvent is preferred, since it is easy to make the composition have excellent storage stability.
[0157] Examples of the organic solvent include carbonates such as propylene carbonate, ethylene carbonate, 1,2-butylene carbonate, dimethyl carbonate, and diethyl carbonate; ketones such as acetone, methyl ethyl ketone, cyclohexanone, methyl isoamyl ketone, and 2-heptanone; polyhydric alcohols and derivatives thereof such as ethylene glycol, ethylene glycol monoacetate, diethylene glycol, diethylene glycol monoacetate, propylene glycol, propylene glycol monoacetate, dipropylene glycol, and monomethyl ether, monoethyl ether, monopropyl ether, monobutyl ether, and monophenyl ether of dipropylene glycol monoacetate; cyclic ethers such as dioxane; ethyl formate, methyl lactate, ethyl lactate, methyl acetate, and the like. Examples of the solvent include ethyl acetate, butyl acetate, methyl pyruvate, methyl acetoacetate, ethyl acetoacetate, ethyl pyruvate, ethyl ethoxyacetate, methyl methoxypropionate, ethyl ethoxypropionate, methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, methyl 2-hydroxy-3-methylbutanoate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, and other esters; toluene, xylene, and other aromatic hydrocarbons; and γ-caprolactone, δ-caprolactone, ε-caprolactone, dimethyl-ε-caprolactone, δ-valerolactone, γ-valerolactone, and γ-butyrolactone, and these solvents can be used alone or in the form of a mixed solvent of two or more kinds. In the present disclosure, the organic solvent is preferably a ketone. This is because the composition can be easily made to have excellent storage stability. In addition, the organic solvent is easy to handle in terms of ease of manufacture, safety, etc.
[0158] The content of the solvent may be any content that can obtain the desired balance of storage stability, electrical properties, and adhesive strength, but is preferably 1 part by mass or more and 99 parts by mass or less in 100 parts by mass of the composition, more preferably 30 parts by mass or more and 90 parts by mass or less, and particularly preferably 50 parts by mass or more and 80 parts by mass or less. This is because the composition can be easily made to have an excellent balance of storage stability, electrical properties, and adhesive strength. In addition, the coating property of the composition can be easily adjusted.
[0159] 7. Composition The composition of the present disclosure contains a cyclic ether component, a latent curing agent, and an elastomer, and optionally contains other resin components, other curing agents, and solvents, and may further contain other components as necessary. Examples of the other components include various additives such as silane coupling agents, inorganic fillers, organic fillers, colorants such as pigments and dyes, photosensitizers, defoamers, thickeners, thixotropic agents, surfactants, leveling agents, flame retardants, plasticizers, stabilizers, polymerization inhibitors, ultraviolet absorbers, antioxidants, antistatic agents, flow adjusters, and adhesion promoters. The other components may also include a radical polymerizable compound, a radical polymerization initiator (a photoradical polymerization initiator, a thermal radical polymerization initiator), and the like. The other components may be added as necessary, and the total content of them is preferably 30 parts by mass or less per 100 parts by mass of the total of the cyclic ether component, the latent curing agent, and the elastomer. The composition has an excellent balance of storage stability, electrical properties, and adhesive strength.
[0160] The method for producing the composition is not particularly limited as long as it is a method that can uniformly mix the above components, and for example, a method of adding a latent curing agent and an elastomer to a cyclic ether component and mixing them can be used. As a mixing method, a method using a known mixing device can be adopted, and for example, a method using a three-roll mill, a sand mill, a ball mill, etc. can be used.
[0161] The uses of the composition are not particularly limited as long as a balance between storage stability, electrical properties, and adhesive strength is required. Examples of the uses of the composition include adhesives, resist materials for printed wiring boards, various coating fields such as resist inks, pigment resist inks for car filters, semiconductor sealants, inks, plastic paints, paper printing, film coatings, glass coatings, shatterproof paints, and furniture paints, FRP, linings, and further display media in the electronics field such as insulating varnishes, insulating sheets, laminates, plasma display panels, and display elements, optical anisotropics such as retardation plates, polarizing plates, light polarizing prisms, and various light filters, adhesives, insulating materials, structural materials, and optical waveguide clads.
[0162] In the present disclosure, the above-mentioned use is preferably as an adhesive, and in particular, it is preferably for bonding conductive materials and insulating materials, and for bonding insulating materials and insulating materials, because the effect of excellent adhesive strength and electrical properties can be effectively exhibited. When the composition is used as an adhesive, the insulating material to be bonded may be a material used as an insulating substrate in a circuit board. For example, the insulating material may be a material having a dielectric loss tangent (1 GHz) of 0.01 or less. Examples of such insulating materials include organic insulating materials such as polyimide (PI), polyethylene terephthalate (PET), polyethylene naphthalate (PEN), fluororesin (PTFE, etc.), polyphenylene ether, and liquid crystal polymer (LCP), and inorganic oxide materials such as glass. An example of a combination of a conductive material and an insulating material is a combination of an organic insulating material and a metal material or a carbon material, such as a laminate formed by bonding a liquid crystal polymer film and copper foil. Examples of combinations of insulating materials include combinations of organic insulating materials, such as a laminate formed by bonding a film of liquid crystal polymer to another film of liquid crystal polymer, and combinations of an organic insulating material such as a liquid crystal polymer with an inorganic oxide material such as glass.
[0163] B. Cured product Next, the cured product of the present disclosure will be described. The cured product of the present disclosure is a cured product of the composition of the present disclosure described above.
[0164] According to the present disclosure, since the above-mentioned composition is used, it is possible to provide a cured product having an excellent balance of storage stability, electrical properties, and adhesive strength. The composition of the present disclosure is similar to that described in the above section "A. Composition," and therefore will not be described here.
[0165] The uses of the cured product of the present disclosure may be similar to those described in the section "A. Composition" above.
[0166] The method for producing the cured product of the present disclosure may be any method capable of curing the composition of the present disclosure. The method for producing the cured product of the present disclosure may be a method described later in "C. Method for producing the cured product".
[0167] C. Manufacturing method of the cured product Next, a method for producing the cured product of the present disclosure will be described. The method for producing a cured product according to the present disclosure is characterized by having a curing step of curing the cyclic ether components in the composition.
[0168] According to the present disclosure, since the above-mentioned composition is used, a cured product having an excellent balance of storage stability, electrical properties, and adhesive strength can be easily obtained.
[0169] 1.Curing process The curing step in the present disclosure is a step of curing the cyclic ether components in the composition together. In this step, the curing method may be any method capable of curing the cyclic ether components together, and examples of the method include a method in which a heat treatment is performed.
[0170] The heating temperature in the heat treatment may be any temperature that can stably cure the composition, and is appropriately set according to the type of the latent curing agent, and may be, for example, 50°C or higher and 250°C or lower, preferably 100°C or higher and 200°C or lower, and particularly preferably 100°C or higher and 190°C or lower. The heating time may be 1 minute or higher and 2 hours or lower, preferably 3 minutes or higher and 1 hour and 30 minutes or lower, and preferably 5 minutes or higher and 70 minutes or lower. This is because the effect of the composition having excellent balance between storage stability, electrical properties, and adhesive strength can be more effectively exhibited. The composition described above can be the same as that described in the section "A. Composition," so a description thereof will be omitted here.
[0171] 2.Other processes The method for producing a cured product according to the present disclosure may include other steps as necessary, such as a pre-bake step in which the composition is heat-treated to remove the solvent in the composition before the curing step, and a step in which a coating film of the composition according to the present disclosure is formed before the curing step.
[0172] The heating conditions in the pre-baking step may be any conditions that can remove the solvent in the composition, and may be, for example, at 70° C. or higher and 150° C. or lower for 30 to 300 seconds.
[0173] In the step of forming a coating film, the composition can be applied by a known method such as a spin coater, a roll coater, a bar coater, a die coater, a curtain coater, various printing methods, immersion, etc. Such a coating film can be formed on a substrate.
[0174] The substrate can be appropriately selected depending on the application of the cured product, and examples thereof include the objects on which the cured product is formed, as described in the above section "A. Composition." After being formed on a substrate, the cured product of the present disclosure may be peeled off from the substrate and used, or transferred from the substrate to another adherend and used.
[0175] The present disclosure is not limited to the above-described embodiments. The above-described embodiments are merely examples, and any embodiment that has substantially the same configuration as the technical idea described in the claims of the present disclosure and exhibits similar effects is included in the technical scope of the present disclosure. EXAMPLES
[0176] The present disclosure will be described in more detail below by giving examples, but the present disclosure is not limited to these examples. In the following examples, among Examples 1 to 26, Examples 1 to 4, 10, 12, and 13 are outside the scope of the present invention.
[0177] [Examples 1 to 26 and Comparative Examples 1 to 4] Compositions were obtained by blending the components according to the formulations shown in the following Tables 1 to 4. The following materials were used for each component. The blending amounts in the tables indicate parts by mass of each component.
[0178] (Elastomer component) A1: Tufprene A (SBS manufactured by Asahi Kasei Corporation, styrene content 40% by mass, MFR 200°C, 5kgf: 13g / 10min, density 0.95g / cm 3 ) A2: Asaprene T439 (SBS manufactured by Asahi Kasei Corporation, styrene content 45% by mass, density 0.95 g / cm 3 ) A3: Asaprene T438 (SBS manufactured by Asahi Kasei Corporation, styrene content 35% by mass, MFR 200°C, 5kgf: 25g / 10min, density 0.94g / cm 3 ) A4:TR2250 (SBS made by JSR, styrene content 52% by mass, MFR200℃, 5kgf:4g / 10min, specific gravity 0.98) A5:DYNARON9901P (SEBS manufactured by JSR, styrene content 53% by mass, MFR230℃, 2.16kgf:3.3g / 10min, specific gravity 0.97) A6: Tuftec H1043 (Asahi Kasei SEBS, styrene content 67% by mass, MFR 230°C, 2.16kgf: 2.0g / 10min, density 0.97g / cm 3 ) A7: Tuftec P2000 (Asahi Kasei SEBS, styrene content 67% by mass, MFR 230°C, 2.16kgf: 3.0g / 10min, density 0.98g / cm 3 )
[0179] (Cyclic ether component) B1: A compound represented by the following formula (B1) (aromatic epoxy compound) B2: Compounds represented by the following formula (B2) (aliphatic epoxy compounds, aliphatic ring-containing epoxy compounds) B3: Compound represented by the following formula (B3) (aromatic epoxy compound, aliphatic ring-containing epoxy compound, polyglycidyl ether of dicyclopentadiene-phenol polymer, "XD1000" manufactured by Nippon Kayaku Co., Ltd., epoxy equivalent 254, softening point by ring and ball method 68 to 78°C) B4: Compound represented by the following formula (B4) (aromatic epoxy compound, aromatic ring-containing epoxy compound, novolac-type epoxy compound having a biphenyl structure, "NC-3000" manufactured by Nippon Kayaku Co., Ltd., epoxy equivalent 280, softening point by ring and ball method 53 to 63°C)
[0180] [ka]
[0181] (Latent hardener) C1: 1-Butyl-3-methylimidazolium dicyanamide (latent curing agent, ionic liquid compound, salt of nitrogen-containing heterocyclic cation and cyanate anion)
[0182] (Other resin components) D1: Phenylene ether resin (other resin components, resin having a phenylene ether skeleton, (modified polyphenylene ether represented by the above general formula (2) (R in general formula (a) 11 , R 12 , R 13 , R 16 , R 17 , R 18 is a methyl group, and R 14 , R 15is a hydrogen atom, L3 is a direct bond, and R 27 , R 28 is a methyl group, and R 29 , R 30 is a hydrogen atom, Mn=1200), "OPE1200st", manufactured by Mitsubishi Gas Chemical Co., Ltd.
[0183] (solvent) E1: Methyl ethyl ketone (MEK)
[0184] [evaluation] The adhesive strength, electrical properties, and storage stability of each composition obtained were evaluated according to the following procedures. The results are shown in Tables 1 to 4. In the tables, evaluation results columns with a diagonal line indicate that evaluation tests were not performed because a cured product could not be obtained or for other reasons.
[0185] 1.Adhesive strength The compositions obtained in the examples and comparative examples were applied using a dispenser onto a first substrate, an LCP substrate (E5508 manufactured by Sumitomo Chemical Co., Ltd., thickness 2 mm), so that the thickness after curing (thickness of the adhesive layer) was 20 μm, and then the solvent was removed by heat treatment at 80° C. for 3 minutes. Next, a second substrate, a copper substrate (a 1.6 mm thick copper-clad laminate (count: No. 35) manufactured by Sanhayato), was placed on the dried coating film, and then heat treatment was performed at 180°C for 60 minutes to obtain a sample for evaluation. Using this evaluation sample, peel strength was measured according to a method conforming to JIS K 6850 "Test method for tensile shear bond strength of adhesives." A small tabletop tester EZ-X (manufactured by Shimadzu Corporation) was used as the measuring device, and the shear adhesive strength (MPa) was measured under conditions of a measurement temperature of 25°C and a tensile speed of 5 mm / min. From the measurement results, the adhesive strength was evaluated according to the following criteria. The results are shown in Tables 1 to 4.
[0186] <Evaluation criteria> ++: 5MPa or more +: 1MPa or more and less than 5MPa -: Less than 1MPa The larger the adhesive strength (MPa), the better the adhesive strength.
[0187] 2.Electrical characteristics 2 g of each of the compositions of the Examples and Comparative Examples was placed in a release-treated screw tube (20 cc) and heated at 60° C. for 12 hours to remove the solvent, thereby obtaining a resin film. The resin film had a thickness of 500 μm. The obtained resin film was heated at 180° C. for 60 minutes to prepare a sample for evaluation.
[0188] The dielectric constant and dielectric loss tangent of the evaluation sample were measured at a frequency of 1 GHz using an impedance / material analyzer E4991A manufactured by Agilent Technologies, and the evaluation was performed according to the following criteria. The results are shown in Tables 1 to 4.
[0189] <Evaluation criteria> (Dielectric constant) +++: Less than 2.6 ++: 2.6 or more and less than 3.2 -:3.2 or higher The smaller the relative dielectric constant, the more excellent the electrical properties.
[0190] (Dielectric tangent) +++: Less than 0.005 ++: 0.005 or more and less than 0.01 +: 0.01 or more and less than 0.015 -:0.015 or more The smaller the dielectric tangent, the more excellent the electrical properties.
[0191] 3.Storage stability The compositions of the Examples and Comparative Examples were left to stand at 23° C. for one week, after which the compositions were visually observed and the storage stability was evaluated according to the following criteria. The results are shown in Tables 1 to 4. <Evaluation criteria> ++: No turbidity (white turbidity) was observed. +: Cloudiness (white turbidity) was observed, but no precipitate was observed. -: Phase separation or precipitation was confirmed in the composition. The composition is judged to have better storage stability when it has less turbidity and precipitates.
[0192] [Table 1]
[0193] [Table 2]
[0194] [Table 3]
[0195] [Table 4]
[0196] [summary] It was confirmed from Tables 1 to 4 that the compositions of the examples have an excellent balance of storage stability, electrical properties, and adhesive strength.
Claims
1. A cyclic ether component; A latent hardener; A styrene-ethylene-butylene-styrene resin having a styrene content of 50% by mass or more and 90% by mass or less; Including, the latent curing agent is an ionic liquid compound containing a nitrogen-containing aromatic heterocyclic cation, The content of the styrene-ethylene-butylene-styrene resin is 30 parts by mass or more in a total of 100 parts by mass of the cyclic ether component, the latent curing agent, and the styrene-ethylene-butylene-styrene resin.
2. 2. The composition of claim 1, wherein the cyclic ether component comprises at least one of an aromatic epoxy compound and an aliphatic epoxy compound containing an aliphatic ring.
3. 3. The composition according to claim 1, wherein the anion of the ionic liquid compound comprises at least one of a cyanate-based anion and a carboxylate-based anion.
4. 4. The composition according to claim 1, wherein the content of the ionic liquid compound is 0.1 parts by mass or more and 30 parts by mass or less per 100 parts by mass of the cyclic ether component and the ionic liquid compound combined.
5. The composition according to claim 1 , further comprising a resin having a phenylene ether skeleton.
6. A cured product of the composition according to any one of claims 1 to 5.
7. A method for producing a cured product, comprising a curing step of curing the cyclic ether components in the composition according to claim 1 .
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