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WO2024242051A1 - Composition de résine, objet durci, préimprégné, stratifié plaqué métal, feuille de résine monocouche, feuille de résine multicouche et carte de circuit imprimé - Google Patents

Composition de résine, objet durci, préimprégné, stratifié plaqué métal, feuille de résine monocouche, feuille de résine multicouche et carte de circuit imprimé Download PDF

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Publication number
WO2024242051A1
WO2024242051A1 PCT/JP2024/018342 JP2024018342W WO2024242051A1 WO 2024242051 A1 WO2024242051 A1 WO 2024242051A1 JP 2024018342 W JP2024018342 W JP 2024018342W WO 2024242051 A1 WO2024242051 A1 WO 2024242051A1
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WIPO (PCT)
Prior art keywords
resin composition
mass
parts
resin
compound
Prior art date
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Pending
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PCT/JP2024/018342
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English (en)
Japanese (ja)
Inventor
尚義 金子
実咲 小椋
環 伊藤
政伸 十亀
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Gas Chemical Co Inc
MGC Electrotechno Co Ltd
Original Assignee
Mitsubishi Gas Chemical Co Inc
MGC Electrotechno Co Ltd
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Application filed by Mitsubishi Gas Chemical Co Inc, MGC Electrotechno Co Ltd filed Critical Mitsubishi Gas Chemical Co Inc
Priority to CN202480033044.6A priority Critical patent/CN121152828A/zh
Publication of WO2024242051A1 publication Critical patent/WO2024242051A1/fr
Anticipated expiration legal-status Critical
Pending legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
    • B32B27/20—Layered products comprising a layer of synthetic resin characterised by the use of special additives using fillers, pigments, thixotroping agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/5399—Phosphorus bound to nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/03—Use of materials for the substrate

Definitions

  • the present invention relates to a resin composition, a cured product thereof, and a prepreg, a metal foil-clad laminate, a single-layer resin sheet, a laminated resin sheet, and a printed wiring board using the resin composition.
  • Cyanate ester resins for example, have been known as materials for forming insulating layers of printed wiring boards (see, for example, Patent Document 1). Cyanate ester resins are thermosetting resins with excellent heat resistance and dielectric properties. However, while dicyclopentadiene-type cyanate ester resins are excellent in heat resistance, low thermal expansion, dielectric properties, and water absorption, they have the problem of being extremely poor in flame retardancy. Patent Document 1 attempts to improve flame retardancy by adding an inorganic filler, but further improvements in properties are desired.
  • the present invention was made based on these problems, and aims to provide a resin composition, a cured product, a prepreg, a metal foil-clad laminate, a single-layer resin sheet, a laminate resin sheet, and a printed wiring board that have excellent heat resistance and flame retardancy.
  • a resin composition comprising a cyanate ester compound (A) represented by the following formula (1), a cyclophosphazene compound (B), and an inorganic filler (C):
  • R1 independently represents a hydrocarbon group having 1 to 8 carbon atoms, i represents an integer of 0 to 3, and n1 represents the number of repetitions, the average value of which is a number of 0 to 5.
  • the inorganic filler (C) includes at least one selected from the group consisting of silicas, aluminum oxide, magnesium hydroxide, aluminum hydroxide, boehmite, boron nitride, aggregated boron nitride
  • the resin composition according to the present invention [4] The resin composition according to [1], further comprising at least one selected from the group consisting of a cyanate ester compound other than the cyanate ester compound (A), an epoxy compound, a phenol compound, a maleimide compound, and a polyphenylene ether compound. [5] The resin composition according to [1], wherein the content of the cyanate ester compound (A) is 10 parts by mass or more and 50 parts by mass or less based on 100 parts by mass of a resin solid content.
  • the present invention contains a cyanate ester compound (A) represented by formula (1), a cyclophosphazene compound (B), and an inorganic filler (C), so it is possible to obtain excellent heat resistance and flame retardancy.
  • A cyanate ester compound represented by formula (1)
  • B cyclophosphazene compound
  • C inorganic filler
  • the present embodiment a form for implementing the present invention (hereinafter referred to as the "present embodiment") will be described in detail, but the present invention is not limited to this, and various modifications are possible without departing from the gist of the present invention.
  • the word "to” is used to mean that the numerical values before and after it are included as the lower limit and upper limit.
  • the notation that does not indicate whether it is substituted or unsubstituted includes both groups (atomic groups) that have no substituents and groups (atomic groups) that have substituents.
  • alkyl group includes not only alkyl groups that have no substituents (unsubstituted alkyl groups), but also alkyl groups that have substituents (substituted alkyl groups).
  • the notation that does not indicate whether it is substituted or unsubstituted is preferably unsubstituted.
  • the "resin solid content in a resin composition” refers to the components in the resin composition excluding fillers (including inorganic fillers) and solvents, and 100 parts by mass of resin solid content refers to the total amount of resin components in the resin composition excluding fillers and solvents being 100 parts by mass.
  • the resin composition according to the present embodiment contains a cyanate ester compound (A) represented by the following formula (1), a cyclophosphazene compound (B), and an inorganic filler (C).
  • A cyanate ester compound represented by the following formula (1)
  • B cyclophosphazene compound
  • C inorganic filler
  • the resin composition according to the present embodiment preferably contains at least one selected from the group consisting of a cyanate ester compound (D) other than the cyanate ester compound (A), an epoxy compound (E), a phenol compound (F), a maleimide compound (G), and a polyphenylene ether compound (H).
  • R1 independently represents a hydrocarbon group having 1 to 8 carbon atoms, i represents an integer of 0 to 3, and n1 represents the number of repetitions, the average value of which is a number of 0 to 5.
  • preferred examples of the hydrocarbon group for R 1 include an alkyl group, an aryl group, an aralkyl group, and an allyl group.
  • the alkyl group may be linear, branched or cyclic, and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, a t-butyl group, a hexyl group, a cyclohexyl group, and a methylcyclohexyl group.
  • aryl group examples include a phenyl group, a tolyl group, a xylyl group, and an ethylphenyl group.
  • aralkyl group examples include a benzyl group and an ⁇ -methylbenzyl group. Of these, a phenyl group or a methyl group is preferred, with a methyl group being particularly preferred.
  • the substitution position of R1 may be any of the ortho, meta, and para positions relative to the cyanato group (-OCN), with the ortho position being preferred.
  • i is the number of substitutions and is preferably 1 or 2, and more preferably 2.
  • n1 represents a number of 0 or more, and its average value (number average) is 0 to 5, preferably 1.0 to 4.0, more preferably 1.1 to 3.0, and even more preferably 1.2 to 2.5.
  • the weight average molecular weight (Mw) of the cyanate ester compound (A) is preferably 400 to 2000, more preferably 400 to 1500, in terms of polystyrene by the GPC method.
  • the number average molecular weight (Mn) is preferably 350 to 1500, more preferably 400 to 1000, in terms of polystyrene by the GPC method.
  • the content of the cyanate ester compound (A) is preferably 10 to 50 parts by mass, more preferably 15 to 45 parts by mass, more preferably 25 to 40 parts by mass, per 100 parts by mass of the resin solid content. By keeping it within this range, it is possible to obtain better heat resistance and higher dielectric properties. Only one type of cyanate ester compound (A) may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount is within the above range.
  • the cyanate ester compound (A) can be obtained, for example, by reacting a halogenated cyanide compound with a phenol under basic conditions.
  • a commercially available cyanate ester compound (A) may also be used.
  • An example of the cyanate ester compound (A) is CO3CO (dicyclopentadiene-type cyanate ester compound) manufactured by YANGZHOU TECHIA MATERIAL.
  • the cyclophosphazene compound (B) functions as a flame retardant, and preferably contains a compound represented by the following formula (2):
  • a compound represented by the following formula (2) By using the cyclophosphazene compound (B) having a phosphorus atom and a nitrogen atom, the flame retardancy can be further improved.
  • Z1 and Z2 each independently represent a vinyl group or a hydrogen atom, and n2 represents an integer of 3 to 8.
  • the content of the cyclophosphazene compound (B) is preferably 3 parts by mass or more and 15 parts by mass or less, more preferably 3 parts by mass or more and 10 parts by mass or less, more preferably 3 parts by mass or more and 9 parts by mass or less, and even more preferably 3 parts by mass or more and 8 parts by mass or less, relative to 100 parts by mass of the resin solid content.
  • the content of the cyclophosphazene compound (B) is preferably 3 parts by mass or more and 15 parts by mass or less, more preferably 3 parts by mass or more and 10 parts by mass or less, more preferably 3 parts by mass or more and 9 parts by mass or less, and even more preferably 3 parts by mass or more and 8 parts by mass or less, relative to 100 parts by mass of the resin solid content.
  • the content of the cyclophosphazene compound (B) is preferably 3 parts by mass or more and 15 parts by mass or less, more preferably 3 parts by mass or more and 10 parts by mass or less, more preferably 3
  • Cyclophosphazene compound (B) represented by formula (2) can be obtained by using, for example, a hexahalogenated cyclotriphosphazene such as hexachlorocyclotriphosphazene as a raw material and substituting the halogen atoms of this hexahalogenated cyclotriphosphazene with aryloxy groups.
  • Cyclophosphazene compound (B) may also be a commercially available product.
  • cyclophosphazene compound (B) may be Rabitol (registered trademark) FP-110 manufactured by Fushimi Pharmaceutical Co., Ltd.
  • the inorganic filler (C) includes at least one selected from the group consisting of silicas, aluminum oxide, magnesium hydroxide, aluminum hydroxide, boehmite, boron nitride, aggregated boron nitride, silicon nitride, and aluminum nitride.
  • silicas include natural silica, fused silica, synthetic silica, amorphous silica, aerosil, and hollow silica.
  • boehmite is preferred as the inorganic charging material (C). Because it is superior.
  • the average particle diameter (D50) of the inorganic filler (C) is preferably 0.1 to 3 ⁇ m, more preferably 0.2 to 2 ⁇ m, and even more preferably 0.3 to 1 ⁇ m.
  • average particle diameter (D50) of the inorganic filler (C) is within the above range, the dispersibility of the inorganic filler (C) in the resin composition is improved, and the flow characteristics during molding are improved.
  • average particle diameter (D50) refers to the diameter of the particles when a predetermined amount of powder is added to an aqueous dispersion medium, the particle size distribution is measured using a laser diffraction particle size distribution analyzer, and the volume is accumulated from the smallest particles to reach 50% of the total volume.
  • the content of the inorganic filler (C) is preferably 50 parts by mass or more and 300 parts by mass or less, and more preferably 70 parts by mass or more and 200 parts by mass or less, per 100 parts by mass of the resin solids. By keeping it within this range, better flame retardancy can be obtained. Only one type of inorganic filler (C) may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount is within the above range.
  • the cyanate ester compound (D) other than the cyanate ester compound (A) is not particularly limited, but is preferably a compound having two or more cyanate groups in the molecule.
  • bisphenol A type cyanate ester compounds and prepolymers thereof, and naphthol aralkyl type cyanate ester compounds are preferred, and at least one of bisphenol A type cyanate ester compounds and naphthol aralkyl type cyanate ester compounds is more preferred.
  • a cyanate ester compound (D) there is a tendency for heat resistance to be further improved.
  • the content of the cyanate ester compound (D) is preferably 15 parts by mass or more and 45 parts by mass or less, and more preferably 25 parts by mass or more and 40 parts by mass or less, per 100 parts by mass of the resin solids. By keeping it within this range, the electrical properties and flame retardancy tend to be further improved. Only one type of cyanate ester compound (D) may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount is within the above range.
  • the epoxy compound (E) is not particularly limited, but is preferably a non-halogen-based compound having two or more epoxy groups in one molecule.
  • Specific examples include bisphenol A type epoxy resin, bisphenol F type epoxy resin, phenol novolac type epoxy resin, bisphenol A novolac type epoxy resin, biphenyl aralkyl type epoxy resin, cresol novolac type epoxy resin, multifunctional phenol type epoxy resin, naphthalene modified epoxy resin, naphthalene skeleton modified novolac type epoxy resin, phenol aralkyl type epoxy resin, biphenyl type epoxy resin, alicyclic epoxy resin, polyol type epoxy resin, phosphorus-containing epoxy resin, glycidylamine, glycidyl ester, butadiene double bond epoxy compound, hydroxyl group-containing silicone resin and epichlorohydrin reaction compound, etc.
  • the content of the epoxy compound (E) is preferably 25 parts by mass or more and 65 parts by mass or less, and more preferably 30 parts by mass or more and 60 parts by mass or less, or 35 parts by mass or more and 55 parts by mass or less, per 100 parts by mass of the resin solids. By keeping it within this range, the metal adhesion, heat resistance, peel strength, and electrical properties tend to be further improved. Only one type of epoxy compound (E) may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount is within the above range.
  • phenol compound (F) a phenol resin having two or more hydroxyl groups in one molecule is preferred, and generally known ones can be used.
  • Specific examples thereof include bisphenol A type phenol resin, bisphenol E type phenol resin, bisphenol F type phenol resin, bisphenol S type phenol resin, novolac type phenol resin, bisphenol A novolac type phenol resin, glycidyl ester type phenol resin, aralkyl novolac type phenol resin, biphenyl aralkyl type phenol resin, cresol novolac type phenol resin, multifunctional phenol resin, naphthol resin, naphthol novolac resin, multifunctional naphthol resin, anthracene type phenol resin, naphthalene skeleton modified novolac type phenol resin, phenol aralkyl type phenol resin, naphthol aralkyl type phenol resin, dicyclopentadiene type phenol resin, biphenyl type phenol
  • the content of the phenol compound (F) is preferably 0.1 parts by mass or more and 10 parts by mass or less, and more preferably 1 part by mass or more and 8 parts by mass or less, and more preferably 2 parts by mass or more and 7 parts by mass or less, per 100 parts by mass of the resin solid content. Only one type of phenol compound (F) may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount is within the above range.
  • the maleimide compound (G) is not particularly limited as long as it has one or more maleimide groups in the molecule. Specific examples include N-phenylmaleimide, N-hydroxyphenylmaleimide, bis(4-maleimidophenyl)methane, 2,2-bis ⁇ 4-(4-maleimidophenoxy)-phenyl ⁇ propane, bis(3,5-dimethyl-4-maleimidophenyl)methane, bis(3-ethyl-5-methyl-4-maleimidophenyl)methane, bis(3,5-diethyl-4-maleimidophenyl)methane, maleimide compounds represented by the following formula (3), prepolymers of these maleimide compounds, or prepolymers of maleimide compounds and amine compounds.
  • the maleimide compound (G) includes at least one selected from the group consisting of maleimide compounds represented by the following formula (3).
  • R6 each independently represents a hydrogen atom or a methyl group, and preferably represents a hydrogen atom.
  • n3 represents an integer of 1 or more, preferably an integer of 10 or less, and more preferably an integer of 7 or less.
  • the content of the maleimide compound (G) can be appropriately set according to the desired characteristics and is not particularly limited, but from the viewpoint of further improving the balance of physical properties of electrical characteristics, heat resistance, and thermal conductivity, it is preferably 1 part by mass or more and 50 parts by mass or less, more preferably 5 parts by mass or more and 30 parts by mass or less, and even more preferably 10 parts by mass or more and 25 parts by mass or less, per 100 parts by mass of resin solids.
  • the content of the maleimide compound (G) is within the above range, the thermal expansion coefficient of the obtained cured product tends to be further reduced and the heat resistance tends to be further improved. Only one type of maleimide compound (G) may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount is within the above range.
  • the polyphenylene ether compound (H) is not particularly limited, but is preferably, for example, a polymer containing a repeating unit represented by the following formula (4). By containing such a polyphenylene ether compound (H), excellent low dielectric constant and low dielectric loss tangent can be obtained, and a uniform cured product tends to be obtained.
  • the polyphenylene ether compound (H) may further contain at least one of a repeating unit represented by the following formula (5) and a repeating unit represented by the following formula (6).
  • R 1 , R 2 , R 3 , and R 4 each independently represent an alkyl group having 6 or less carbon atoms, an aryl group, a halogen atom, or a hydrogen atom.
  • R 5 , R 6 , R 7 , R 11 , and R 12 each independently represent an alkyl group having 6 or less carbon atoms or a phenyl group
  • R 8 , R 9 , and R 10 each independently represent a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group.
  • R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , and R 20 each independently represent a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group, and A represents a linear, branched, or cyclic divalent hydrocarbon group having 20 or less carbon atoms.
  • the polyphenylene ether compound (H) may have a substituent.
  • the substituent is not particularly limited, but examples thereof include ethylenically unsaturated groups such as vinylbenzyl groups, epoxy groups, amino groups, hydroxyl groups, mercapto groups, carboxyl groups, and silyl groups. Among these, ethylenically unsaturated groups are preferred.
  • the polyphenylene ether compound (H) having such a substituent is also referred to as a "modified polyphenylene ether.”
  • ethylenically unsaturated groups are not particularly limited, but examples thereof include alkenyl groups such as ethenyl, allyl, methallyl, propenyl, butenyl, hexenyl, and octenyl; cycloalkenyl groups such as cyclopentenyl and cyclohexenyl; and alkenylaryl groups such as vinylbenzyl and vinylnaphthyl.
  • the vinylbenzyl group is preferred from the viewpoints of electrical properties and low water absorption.
  • the position of the substituent is not particularly limited, but examples include both ends of the polyphenylene ether chain, one end of the polyphenylene ether chain, a side chain of the polyphenylene ether chain, or a combination of these. Among these, from the viewpoint of heat resistance, a polyphenylene ether compound having ethylenically unsaturated groups at both ends is preferred. When the polyphenylene ether compound has two or more substituents, the respective substituents may be the same or different.
  • modified polyphenylene ethers having ethylenically unsaturated groups at both ends are preferred.
  • modified polyphenylene ethers are not particularly limited, but examples thereof include compounds represented by the following formula (7).
  • X represents a group represented by the following formula (8) or formula (9), each Y independently represents a group represented by the following formula (10), and a and b represent integers of 0 to 100, with at least one of them being 1 or greater.
  • R 21 , R 22 , R 23 , R 27 , and R 28 each independently represent an alkyl group having 6 or less carbon atoms or a phenyl group, and R 24 , R 25 , and R 26 each independently represent a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group.
  • R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , and R 36 each independently represent a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group
  • A represents a linear, branched, or cyclic divalent hydrocarbon group having 20 or less carbon atom
  • the divalent hydrocarbon group represented by A is not particularly limited, but examples include methylene, ethylidene, 1-methylethylidene, 1,1-propylidene, 1,4-phenylenebis(1-methylethylidene), 1,3-phenylenebis(1-methylethylidene), cyclohexylidene, phenylmethylene, naphthylmethylene, and 1-phenylethylidene.
  • the compound represented by formula (7) may contain one type of group represented by formula (10), or two or more types.
  • different types of groups represented by formula (10) may be arranged randomly, or the same type of groups represented by formula (10) may be arranged in a block pattern.
  • R 21 , R 22 , R 23 , R 27 , R 28 , R 39 and R 40 are alkyl groups having 3 or less carbon atoms, and R 24 , R 25 , R 26 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 and R
  • a modified polyphenylene ether in which 38 is a hydrogen atom or an alkyl group having 3 or less carbon atoms is preferred, and in particular a modified polyphenylene ether in which X represented by the above formula (8) or (9) is a group represented by the following formula (11), (12), or (13), and Y represented by the above formula (10) is the following formula (14) or (15), or a structure in which the following formulas (14) and (15) are randomly arranged is more preferred.
  • R 31 , R 32 , R 33 and R 34 each independently represent a hydrogen atom or a methyl group.
  • -A- represents a linear, branched or cyclic divalent hydrocarbon group having 20 or less carbon atoms.
  • A is a linear, branched or cyclic divalent hydrocarbon group having 20 or less carbon atoms.
  • the method for producing the modified polyphenylene ether having the structure represented by the above formula (7) is not particularly limited, but may be, for example, a method in which a bifunctional phenol compound and a monofunctional phenol compound are subjected to oxidative coupling to obtain a bifunctional phenylene ether oligomer, and the terminal phenolic hydroxyl group of the obtained bifunctional phenylene ether oligomer is converted to vinylbenzyl ether.
  • a method for producing modified polyphenylene ethers modified with vinylbenzyl groups includes dissolving a bifunctional phenylene ether oligomer and vinylbenzyl chloride in a solvent, and adding a base under heating and stirring to cause a reaction.
  • a method for producing modified polyphenylene ethers modified with carboxyl groups includes melt-kneading polyphenylene ether with an unsaturated carboxylic acid or a functional derivative thereof in the presence or absence of a radical initiator and causing a reaction; or a method for producing modified polyphenylene ethers modified with carboxyl groups includes dissolving polyphenylene ether and at least one of an unsaturated carboxylic acid and a functional derivative thereof in an organic solvent in the presence or absence of a radical initiator and causing a reaction in the solution.
  • the number average molecular weight of the polyphenylene ether compound (H) is 500 to 5000, preferably 700 to 3500, and more preferably 900 to 2500, as calculated as polystyrene by the GPC method.
  • the number average molecular weight of the polyphenylene ether compound (H) is 500 or more, the compound is less sticky when formed into a coating film.
  • the number average molecular weight of the polyphenylene ether compound (H) is 5000 or less, the compound is prevented from decreasing in solubility in a solvent.
  • the content of the polyphenylene ether compound (H) is preferably 1 part by mass or more and 60 parts by mass or less, and more preferably 5 parts by mass or more and 50 parts by mass or less, and more preferably 10 parts by mass or more and 40 parts by mass or less, per 100 parts by mass of the resin solid content. Only one type of polyphenylene ether compound (H) may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount is within the above range.
  • the vinyl group equivalent (g/eq.) of the polyphenylene ether compound (H) is preferably 250 to 2600 g/eq., more preferably 350 to 1800 g/eq., and even more preferably 450 to 1400 g/eq.
  • the vinyl group equivalent (g/eq.) of the polyphenylene ether compound (H) is within the above range, the heat resistance and low water absorption tend to be further improved.
  • a silane coupling agent or a wetting dispersant may be used in combination from the viewpoint of improving the dispersibility of the inorganic filler (C) and the adhesive strength between the resin and the inorganic filler (C) or between the resin and the glass cloth.
  • the silane coupling agent is not particularly limited as long as it is a silane coupling agent generally used for surface treatment of inorganic substances. Specific examples include aminosilane compounds such as ⁇ -aminopropyltriethoxysilane and N- ⁇ -(aminoethyl)- ⁇ -aminopropyltrimethoxysilane; epoxysilane compounds such as ⁇ -glycidoxypropyltrimethoxysilane; vinylsilane compounds such as ⁇ -methacryloxypropyltrimethoxysilane; cationic silane compounds such as N- ⁇ -(N-vinylbenzylaminoethyl)- ⁇ -aminopropyltrimethoxysilane hydrochloride; and phenylsilane compounds.
  • the silane coupling agent can be used alone or in combination of two or more.
  • wetting and dispersing agent those generally used for paints can be suitably used, and the type is not particularly limited.
  • wetting and dispersing agents such as Disperbyk-110, 111, 180, 161, BYK-W996, W9010, and W903 manufactured by BYK-Chemie Japan Co., Ltd. can be mentioned.
  • thermosetting resins thermoplastic resins and their oligomers
  • various polymeric compounds such as elastomers, other flame-retardant compounds, additives, etc., other than those mentioned above, can be used in combination as necessary.
  • flame-retardant compounds include phosphate esters, melamine phosphate, phosphorus-containing epoxy resins, nitrogen compounds such as melamine and benzoguanamine, oxazine ring-containing compounds, silicone compounds, etc.
  • Additives include ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent brighteners, photosensitizers, dyes, pigments, thickeners, lubricants, defoamers, dispersants, leveling agents, gloss agents, etc., and can be used in appropriate combination as desired.
  • a curing accelerator can be used in combination as necessary to appropriately adjust the curing speed.
  • examples of such compounds include organic peroxides exemplified by benzoyl peroxide, lauroyl peroxide, acetyl peroxide, parachlorobenzoyl peroxide, di-tert-butyl-di-perphthalate, and the like; azo compounds such as azobisnitrile; tertiary amines such as N,N-dimethylbenzylamine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2-N-ethylanilinoethanol, tri-n-butylamine, pyridine, quinoline, N-methylmorpholine, triethanolamine, triethylenediamine, tetramethylbutanediamine, and N-methylpiperidine; 2-ethyl-4-methylimidazole, 2-furan, and the like.
  • imidazoles such as phenyl-4-methylimidazole and triphenylimidazole
  • monomeric phenols such as phenol, xylenol, cresol, resorcin, and catechol
  • organic metal salts such as lead naphthenate, lead stearate, zinc naphthenate, zinc octoate, tin oleate, dibutyltin malate, manganese naphthenate, cobalt naphthenate, and iron acetylacetonate; these organic metal salts dissolved in monomeric hydroxyl group-containing compounds such as phenol and bisphenol; inorganic metal salts such as tin chloride, zinc chloride, and aluminum chloride; and organic tin compounds such as dioctyltin oxide, other alkyl tins, and alkyl tin oxides.
  • the resin composition of the present embodiment may contain a solvent as necessary.
  • a solvent for example, when an organic solvent is used, the viscosity during preparation of the resin composition is reduced, the handling property is improved, and the impregnation property into the glass cloth is enhanced.
  • the type of solvent is not particularly limited as long as it can dissolve a part or all of the mixture of the cyanate ester compound (A) and the cyclophosphazene compound (B).
  • ketones such as acetone and methyl ethyl ketone
  • aromatic hydrocarbons such as toluene and xylene
  • amides such as dimethylformamide
  • cellosolves such as methyl cellosolve, propylene glycol methyl ether and its acetate.
  • the solvent can be used alone or in combination of two or more.
  • the resin composition according to the present embodiment can be prepared according to a conventional method, and the preparation method is not particularly limited as long as it is a method that can obtain a resin composition that uniformly contains the cyanate ester compound (A), the cyclophosphazene compound (B), the inorganic filler (C), and, if necessary, the other optional components described above.
  • the resin composition according to the present embodiment can be easily prepared by sequentially blending the cyanate ester compound (A), the cyclophosphazene compound (B), and the inorganic filler (C) in a solvent and thoroughly stirring the mixture.
  • known processes such as stirring, mixing, and kneading
  • stirring, mixing, and kneading can be carried out to uniformly dissolve or disperse each component.
  • the dispersibility in the resin composition can be improved by carrying out a stirring and dispersing process using a stirring tank equipped with a stirrer having appropriate stirring capacity.
  • the above stirring, mixing, and kneading processes can be appropriately carried out using, for example, a device for mixing such as a ball mill or a bead mill, or a known device such as a revolution/rotation type mixer.
  • the resin composition according to the present embodiment can be suitably used as a cured product, a prepreg, a metal foil-clad laminate, a single-layer resin sheet, a laminated resin sheet, or a printed wiring board.
  • the properties of heat resistance and flame retardancy are required.
  • the resin composition according to the present embodiment is useful because it can provide excellent heat resistance and flame retardancy.
  • the prepreg, the metal foil-clad laminate, the single-layer resin sheet, the laminated resin sheet, or the printed wiring board will be described.
  • the cured product of this embodiment is obtained by curing the resin composition of this embodiment with heat, light, or the like.
  • the cured product can be obtained by melting or dissolving or dispersing the curable resin composition in a solvent, pouring it into a mold, removing the solvent by reducing pressure as necessary, and then curing it under normal conditions.
  • heat curing it is preferable to cure the curable resin composition at 65°C to 250°C, more preferably at 120°C to 230°C, and even more preferably at 150°C to 200°C.
  • the curing temperature during heat curing is not particularly limited, and the curing may be performed at a constant curing temperature, or the curing may be performed by a step cure in which the heating process is held at a constant temperature for a certain period of time twice or more.
  • the prepreg of the present embodiment has a base material and the above-mentioned resin composition impregnated or applied to the base material.
  • the method for producing the prepreg can be carried out according to a conventional method, and is not particularly limited.
  • the prepreg of the present embodiment can be produced by impregnating or applying the resin composition of the present embodiment to the base material, and then semi-curing (B-stage) by heating in a dryer at 100°C to 200°C for 1 to 30 minutes.
  • the content of the resin composition is preferably 30% by mass to 90% by mass, more preferably 35% by mass to 85% by mass, and preferably 40% by mass to 80% by mass, relative to the total amount of the prepreg. By keeping the content of the resin composition within the above range, moldability tends to be further improved.
  • the substrate used in this embodiment is not particularly limited, and may be appropriately selected from known materials used in various printed wiring board materials depending on the intended use and performance. Specific examples include, but are not limited to, glass fibers such as E glass, D glass, S glass, Q glass, spherical glass, NE glass, L glass, and T glass; inorganic fibers other than glass such as quartz; wholly aromatic polyamides such as polyparaphenylene terephthalamide (Kevlar (registered trademark), manufactured by DuPont Co., Ltd.) and copolyparaphenylene-3,4'-oxydiphenylene-terephthalamide (Technora (registered trademark), manufactured by Teijin Techno Products Co., Ltd.); polyesters such as 2,6-hydroxynaphthoic acid-parahydroxybenzoic acid (Vectran (registered trademark), manufactured by Kuraray Co., Ltd.) and Zexion (registered trademark, manufactured by KB Seiren); organic fibers such as polyparaphenylene be
  • Examples of the shape of the substrate include woven fabric, nonwoven fabric, roving, chopped strand mat, surfacing mat, etc.
  • Examples of the weaving method of the woven fabric include plain weave, sash weave, twill weave, etc.
  • the shape and weaving method of the substrate can be appropriately selected from these known ones depending on the intended use and performance.
  • a substrate that has been subjected to fiber opening treatment or a glass woven fabric that has been surface-treated with a silane coupling agent or the like is preferably used.
  • the thickness and mass of the substrate are not particularly limited, but a substrate having a thickness of about 0.01 mm to 0.3 mm is usually preferably used.
  • the substrate is preferably a glass woven fabric having a thickness of 200 ⁇ m or less and a mass of 250 g/m 2 or less, and more preferably a glass woven fabric made of E-glass glass fibers.
  • the metal foil-clad laminate of this embodiment has one or more laminates of the above prepregs and a metal foil laminated on one or both sides of the laminate.
  • the manufacturing method of the metal foil-clad laminate can be performed according to a conventional method and is not particularly limited. For example, it can be obtained by stacking at least one or more of the above prepregs, arranging a metal foil on one or both sides of the prepregs, and laminating and molding the metal foil. More specifically, the metal foil-clad laminate of this embodiment can be produced by stacking one or more of the above prepregs, arranging a metal foil such as copper or aluminum on one or both sides of the prepregs as desired, and laminating and molding the resulting structure as necessary.
  • the metal foil used here is not particularly limited as long as it is used in printed wiring board materials, but known copper foils such as rolled copper foil and electrolytic copper foil are preferred.
  • the thickness of the metal foil is not particularly limited, but is preferably 2 ⁇ m to 70 ⁇ m, more preferably 2 ⁇ m to 35 ⁇ m.
  • the molding method and molding conditions of the metal foil-clad laminate are also not particularly limited, and general methods and conditions for laminates and multilayer boards for printed wiring boards can be applied. For example, when molding the metal foil-clad laminate, a multistage press machine, a multistage vacuum press machine, a continuous molding machine, an autoclave molding machine, etc. can be used, and the temperature is generally 100° C.
  • the pressure is a surface pressure of 2 kgf/cm 2 to 100 kgf/cm 2
  • the heating time is generally in the range of 0.05 hours to 5 hours.
  • post-curing can be performed at a temperature of 150° C. to 300° C. as necessary.
  • the metal foil-clad laminate of the present embodiment described above can be suitably used as a printed wiring board by forming a predetermined wiring pattern.
  • the laminated resin sheet of the present embodiment has a sheet substrate and a resin composition layer formed by applying and drying the resin composition on one or both sides of the sheet substrate.
  • the method for producing the laminated resin sheet can be performed according to a conventional method and is not particularly limited.
  • the laminated resin sheet can be obtained by applying a solution in which the resin composition of the present embodiment is dissolved or dispersed in a solvent to the sheet substrate and drying the solution.
  • the sheet substrate used here is not particularly limited, but examples include polyethylene film, polypropylene film, polycarbonate film, polyethylene terephthalate film, ethylene tetrafluoroethylene copolymer film, and release films obtained by applying a release agent to the surface of these films, organic film substrates such as polyimide film, conductive foils such as copper foil and aluminum foil, glass plate, SUS plate, FRP, and other plate-shaped substrates, but is not particularly limited to these.
  • Examples of application methods include a method in which a solution in which the resin composition of this embodiment is dissolved or dispersed in a solvent is applied onto a sheet substrate using a bar coater, die coater, doctor blade, baker applicator, or the like.
  • the single-layer resin sheet of this embodiment is obtained by forming the resin composition into a sheet shape.
  • the method for producing the single-layer resin sheet can be performed according to a conventional method, and is not particularly limited.
  • a solution in which the resin composition of this embodiment is dissolved or dispersed in a solvent is applied to a sheet substrate, dried, and then the sheet substrate is peeled off or etched from the laminated resin sheet.
  • the drying conditions for removing the solvent are not particularly limited, but since low temperatures tend to leave the solvent in the resin composition, and high temperatures cause the resin composition to harden, drying at a temperature of 20°C to 170°C for 1 minute to 90 minutes is preferred.
  • the thickness of the resin composition layer of the single layer or laminate sheet of this embodiment can be adjusted by the concentration of the solution of the resin composition of this embodiment and the coating thickness, and is not particularly limited. However, a thicker coating thickness generally makes it easier for solvent to remain when dried, so a thickness of 0.1 ⁇ m to 500 ⁇ m is preferred.
  • the printed wiring board of the present embodiment has an insulating layer and a conductor layer formed on one or both sides of the insulating layer, and the insulating layer includes a cured product of the resin composition.
  • the method for manufacturing the printed wiring board can be performed according to a conventional method and is not particularly limited.
  • the printed wiring board can be manufactured by the following method. First, a metal foil-clad laminate such as a copper-clad laminate of the present embodiment is prepared. An inner layer circuit is formed by etching the surface of the metal foil-clad laminate to prepare an inner layer substrate.
  • a surface treatment is performed on the inner layer circuit surface of this inner layer substrate to increase the adhesive strength, and then a required number of prepregs of the present embodiment are stacked on the inner layer circuit surface, and a metal foil for an outer layer circuit is further stacked on the outside thereof, and the resulting product is molded by heating and pressing.
  • a multilayer laminate is manufactured in which an insulating layer made of a base material and a cured product of the resin composition is formed between the inner layer circuit and the metal foil for the outer layer circuit.
  • the multilayer laminate is subjected to a hole punching process for through holes and via holes, and then a desmear process is performed to remove smears, which are resin residues derived from the resin components.
  • a plated metal film is then formed on the wall surface of this hole to provide electrical continuity between the inner layer circuit and the metal foil for the outer layer circuit, and the metal foil for the outer layer circuit is then etched to form the outer layer circuit, thereby producing a printed wiring board.
  • the laminated resin sheet or single-layered resin sheet of this embodiment can be used instead of the metal foil-clad laminate or prepreg.
  • the laminated resin sheet or single-layered resin sheet of this embodiment is laminated on the surface of the inner layer circuit, a multi-layered laminate is produced in which an insulating layer made of a cured resin composition is formed between the inner layer circuit and the metal foil for the outer layer circuit.
  • the resin composition contains the cyanate ester compound (A) represented by formula (1), the cyclophosphazene compound (B), and the inorganic filler (C), so that excellent heat resistance and flame retardancy can be obtained.
  • Cyanate ester compound (A) represented by formula (1) (dicyclopentadiene type cyanate ester compound (DCPD type CN) CO3CO YANGZHOU TECHIA
  • the epoxy compound (E) 40 parts by mass of a biphenyl aralkyl type epoxy resin (NC-3000FH, manufactured by Nippon Kayaku Co., Ltd.) and 10 parts by mass of a cresol novolac type epoxy resin (N680, manufactured by DIC Corporation) were used.
  • phenol compound (F) 3.0 parts by mass of an aminotriazine-containing novolac type phenolic resin (LA-3018, manufactured by DIC Corporation) were used.
  • maleimide compound (G) 12 parts by mass of 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide (BMI-5100, manufactured by Daiwa Kasei Kogyo Co., Ltd.) were used.
  • cyclophosphazene compound (B) 5.0 parts by mass of hexaphenoxycyclotriphosphazene (Rabitor (registered trademark) FP-110, manufactured by Fushimi Pharmaceutical Co., Ltd.) were used.
  • boehmite As the inorganic filler (C), boehmite (Apyral AOH60 (manufactured by Nabaltec), 150 parts by mass, was mixed and diluted with methyl ethyl ketone to a solid content of 60% by mass to obtain a varnish.
  • the composition of the resin composition is shown in Table 1.
  • the varnish obtained was impregnated and coated on an E-glass cloth having a thickness of 0.09 mm (IPC No. #2116), and dried by heating at 170°C for 5 minutes using a dryer (pressure-resistant explosion-proof steam dryer, manufactured by Takasugi Seisakusho Co., Ltd.), to obtain a prepreg containing 49% by mass of the resin composition.
  • Eight sheets of the prepreg were stacked, and 12 ⁇ m copper foil (3EC-VLP, manufactured by Mitsui Mining & Smelting Co., Ltd.) was placed on both sides, and vacuum pressing was performed at a pressure of 30 kg/cm 2 and a temperature of 210°C for 150 minutes to obtain a 12 ⁇ m copper-clad laminate having a thickness of 0.8 mm.
  • the copper foil on both sides of the obtained copper-clad laminate was removed by etching to obtain a laminate.
  • evaluation of flame retardancy and moldability were performed.
  • the laminate was cut into 5 pieces of 125 mm x 13 mm x 0.8 mm to obtain test samples.
  • the test samples were attached vertically to a clamp and exposed to a 20 mm flame for 10 seconds twice to measure the burning time, in accordance with the UL94 vertical test method.
  • the laminate was cut into a size of 300 mm x 300 mm x 0.8 mm. Both sides of the obtained sample were observed to check whether or not flow marks were generated. If flow marks were generated, the longest length of the flow marks from the end of the sample was measured. The results obtained are shown in Table 1.
  • Example 2 Except for changing the composition of the resin composition as shown in Table 1, varnishes and copper-clad laminates were prepared in the same manner as in Example 1, and the flame retardancy and moldability were evaluated in the same manner as in Example 1.
  • the content of the cyclophosphazene compound (B) was 3.0 parts by mass per 100 parts by mass of the resin solid content.
  • the composition of the resin composition, the flame retardancy evaluation, and the moldability evaluation are also shown in Table 1.
  • Example 3 Except for changing the composition of the resin composition as shown in Table 1, a varnish and a copper-clad laminate were prepared in the same manner as in Example 1, and the flame retardancy and moldability were evaluated in the same manner as in Example 1.
  • the content of the cyclophosphazene compound (B) was 8.0 parts by mass per 100 parts by mass of the resin solid content.
  • the composition of the resin composition, the flame retardancy evaluation, and the moldability evaluation are also shown in Table 1.
  • Example 4 Except for changing the composition of the resin composition as shown in Table 1, a varnish and a copper-clad laminate were prepared in the same manner as in Example 1, and the flame retardancy and moldability were evaluated in the same manner as in Example 1.
  • the content of the cyclophosphazene compound (B) was 9.0 parts by mass per 100 parts by mass of the resin solid content.
  • the composition of the resin composition, the flame retardancy evaluation, and the moldability evaluation are also shown in Table 1.
  • Example 5 Except for changing the composition of the resin composition as shown in Table 1, varnishes and copper-clad laminates were prepared in the same manner as in Example 1, and the flame retardancy and moldability were evaluated in the same manner as in Example 1.
  • the content of the cyclophosphazene compound (B) was 9.9 parts by mass per 100 parts by mass of the resin solid content.
  • the composition of the resin composition, the flame retardancy evaluation, and the moldability evaluation are also shown in Table 1.
  • Example 6 Except for changing the composition of the resin composition as shown in Table 2, varnishes and copper-clad laminates were prepared in the same manner as in Example 1, and the flame retardancy and moldability were evaluated in the same manner as in Example 1.
  • the content of the cyclophosphazene compound (B) was 10.0 parts by mass per 100 parts by mass of the resin solid content.
  • the composition of the resin composition, the flame retardancy evaluation, and the moldability evaluation are also shown in Table 2.
  • Example 7 Except for changing the composition of the resin composition as shown in Table 2, a varnish and a copper-clad laminate were prepared in the same manner as in Example 1, and the flame retardancy and moldability were evaluated in the same manner as in Example 1.
  • the content of the cyclophosphazene compound (B) was 15.0 parts by mass per 100 parts by mass of the resin solid content.
  • the composition of the resin composition, the flame retardancy evaluation, and the moldability evaluation are also shown in Table 2.
  • Example 8 Except for changing the composition of the resin composition as shown in Table 2, a varnish and a copper-clad laminate were prepared in the same manner as in Example 1, and the flame retardancy and moldability were evaluated in the same manner as in Example 1.
  • Example 8 is an example in which 150 parts by mass of silica (SFP-130MC, manufactured by Denka Co., Ltd.) was mixed in place of boehmite as the inorganic filler (C).
  • SFP-130MC silica
  • boehmite boehmite
  • Example 2 Comparative Example 2 Except for using an aromatic condensed phosphate ester (PX-200, manufactured by Daihachi Chemical Industry Co., Ltd.) as a flame retardant instead of the cyclophosphazene compound (B), a varnish and a copper-clad laminate were prepared in the same manner as in Example 1, and the flame retardancy and moldability were evaluated in the same manner as in Example 1.
  • the composition of the resin composition, the flame retardancy evaluation, and the moldability evaluation are also shown in Table 2.
  • the flame retardancy was judged as being sufficient and indicated as "V-0" when the maximum burning time was less than 10 seconds and the average burning time was less than 5 seconds, and was indicated as being insufficient and indicated as "V-1" when the maximum burning time was 10 seconds or more but less than 30 seconds, or the average burning time was 10 seconds or more but less than 25 seconds.
  • the degree of flame retardancy tended to increase as the content of the cyclophosphazene compound (B) increased. That is, it was found that excellent flame retardancy could be obtained by adding the cyclophosphazene compound (B).
  • Examples 1 to 8 also achieved good moldability.
  • the moldability was evaluated as follows: when the flow mark was less than 8.5 cm, the best moldability was evaluated as " ⁇ ", when the flow mark was 8.5 cm or more and less than 11.5 cm, the good moldability was evaluated as " ⁇ ", and when the flow mark was 11.5 cm or more, the poor moldability was evaluated as " ⁇ ".
  • the content of cyclophosphazene compound (B) is preferably 3 parts by mass or more and 15 parts by mass or less per 100 parts by mass of the resin solid content.
  • Example 1 in which boehmite was used as the inorganic filler (C)
  • Example 8 in which silica was used as the inorganic filler (C)
  • Tables 1 and 2 Example 1, in which boehmite was used as the inorganic filler (C)
  • silica silica was used as the inorganic filler (C)
  • the resin composition of the present invention has industrial applicability as a material for cured products, prepregs, metal foil-clad laminates, single-layer resin sheets, laminated resin sheets, printed wiring boards, etc.

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Abstract

Le problème décrit par la présente invention est de fournir une composition de résine, un objet durci, un préimprégné, un stratifié plaqué métal, une feuille de résine monocouche, une feuille de résine multicouche et une carte de circuit imprimé, tous excellents en termes de résistance à la chaleur et d'ininflammabilité. [Solution] La composition de résine comprend un composé ester d'acide cyanique (A) représenté par la formule (1), un composé cyclophosphazène (B) et une charge inorganique (C). Le composé ester d'acide cyanique (A) confère une excellente résistance à la chaleur et d'excellentes caractéristiques diélectriques, et l'ininflammabilité est améliorée grâce au composé cyclophosphazène (B) et à la charge inorganique (C).
PCT/JP2024/018342 2023-05-23 2024-05-17 Composition de résine, objet durci, préimprégné, stratifié plaqué métal, feuille de résine monocouche, feuille de résine multicouche et carte de circuit imprimé Pending WO2024242051A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009298981A (ja) * 2008-06-17 2009-12-24 Sumitomo Bakelite Co Ltd 樹脂組成物、プリプレグおよびそれを用いたプリント配線板
JP2010285594A (ja) * 2009-02-20 2010-12-24 Ajinomoto Co Inc 樹脂組成物
WO2015133292A1 (fr) * 2014-03-06 2015-09-11 三菱瓦斯化学株式会社 Composition de résine, préimprégné, feuille de résine, plaque laminée revêtue d'une feuille métallique, et circuit imprimé
CN108148178A (zh) * 2016-12-05 2018-06-12 广东生益科技股份有限公司 一种热固性树脂组合物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009298981A (ja) * 2008-06-17 2009-12-24 Sumitomo Bakelite Co Ltd 樹脂組成物、プリプレグおよびそれを用いたプリント配線板
JP2010285594A (ja) * 2009-02-20 2010-12-24 Ajinomoto Co Inc 樹脂組成物
WO2015133292A1 (fr) * 2014-03-06 2015-09-11 三菱瓦斯化学株式会社 Composition de résine, préimprégné, feuille de résine, plaque laminée revêtue d'une feuille métallique, et circuit imprimé
CN108148178A (zh) * 2016-12-05 2018-06-12 广东生益科技股份有限公司 一种热固性树脂组合物

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