WO2006068063A1 - 変性フェノール樹脂、それを含むエポキシ樹脂組成物およびこれを用いたプリプレグ - Google Patents
変性フェノール樹脂、それを含むエポキシ樹脂組成物およびこれを用いたプリプレグ Download PDFInfo
- Publication number
- WO2006068063A1 WO2006068063A1 PCT/JP2005/023183 JP2005023183W WO2006068063A1 WO 2006068063 A1 WO2006068063 A1 WO 2006068063A1 JP 2005023183 W JP2005023183 W JP 2005023183W WO 2006068063 A1 WO2006068063 A1 WO 2006068063A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- epoxy resin
- general formula
- phenolic resin
- resin
- Prior art date
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- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 170
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 159
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 title claims abstract description 134
- 239000000203 mixture Substances 0.000 title claims abstract description 83
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 119
- 150000001875 compounds Chemical class 0.000 claims abstract description 100
- -1 phenol compound Chemical class 0.000 claims abstract description 83
- 239000005011 phenolic resin Substances 0.000 claims abstract description 71
- 229920001568 phenolic resin Polymers 0.000 claims abstract description 41
- 239000011521 glass Substances 0.000 claims abstract description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 21
- 239000000758 substrate Substances 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 229920005603 alternating copolymer Polymers 0.000 claims abstract description 13
- 239000000126 substance Substances 0.000 claims description 141
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 122
- 238000001723 curing Methods 0.000 claims description 111
- 239000004593 Epoxy Substances 0.000 claims description 77
- 239000003795 chemical substances by application Substances 0.000 claims description 70
- 230000001588 bifunctional effect Effects 0.000 claims description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims description 53
- 150000002989 phenols Chemical class 0.000 claims description 48
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- 238000000034 method Methods 0.000 claims description 35
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- 125000005843 halogen group Chemical group 0.000 claims description 23
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- 125000004434 sulfur atom Chemical group 0.000 claims description 21
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- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 11
- 125000006839 xylylene group Chemical group 0.000 claims description 11
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- 229910003475 inorganic filler Inorganic materials 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 238000010030 laminating Methods 0.000 claims description 7
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 11
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 11
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 11
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 11
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- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 11
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- 230000035484 reaction time Effects 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 239000003925 fat Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000000835 fiber Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 7
- 239000000853 adhesive Substances 0.000 description 7
- 230000001070 adhesive effect Effects 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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- 150000003839 salts Chemical class 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 5
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
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- 125000001624 naphthyl group Chemical group 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
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- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
- 125000005838 1,3-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:2])C([H])([H])C1([H])[*:1] 0.000 description 4
- YHKXFIHFUOMWFG-UHFFFAOYSA-N 1-(chloromethyl)-3-[3-(chloromethyl)phenyl]benzene Chemical group ClCC1=CC=CC(C=2C=C(CCl)C=CC=2)=C1 YHKXFIHFUOMWFG-UHFFFAOYSA-N 0.000 description 4
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- GIIXTFIYICRGMZ-UHFFFAOYSA-N tris(2,3-dimethylphenyl)phosphane Chemical compound CC1=CC=CC(P(C=2C(=C(C)C=CC=2)C)C=2C(=C(C)C=CC=2)C)=C1C GIIXTFIYICRGMZ-UHFFFAOYSA-N 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
-
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- 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
- B32B15/00—Layered products comprising a layer of metal
- B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
-
- 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
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/02—Layered products essentially comprising sheet glass, or glass, slag, or like fibres in the form of fibres or filaments
- B32B17/04—Layered products essentially comprising sheet glass, or glass, slag, or like fibres in the form of fibres or filaments bonded with or embedded in a plastic substance
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
-
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/12—Mountings, e.g. non-detachable insulating substrates
- H01L23/14—Mountings, e.g. non-detachable insulating substrates characterised by the material or its electrical properties
- H01L23/145—Organic substrates, e.g. plastic
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
-
- 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
- H05K1/0313—Organic insulating material
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0326—Organic insulating material consisting of one material containing O
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/901—Printed circuit
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31645—Next to addition polymer from unsaturated monomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2926—Coated or impregnated inorganic fiber fabric
- Y10T442/2992—Coated or impregnated glass fiber fabric
Definitions
- the present invention relates to a modified phenolic resin, a method for producing the same, an epoxy resin composition using the same, and a cured product thereof. More specifically, it relates to a modified phenolic resin used for insulating materials for electrical and electronic parts, including epoxy resin hardeners for semiconductor encapsulation, and laminated boards such as printed wiring boards, adhesives, molding materials and paints. .
- the present invention also relates to a pre-preda, a laminate and an electronic circuit board using an epoxy resin composition. More specifically, an epoxy resin composition having improved heat resistance, flame retardancy, and adhesion, which is composed of an epoxy compound or epoxy resin, a curing agent made of modified phenol resin, and a curing accelerator, is made of glass. BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a prepreader impregnated in a base material, a laminate obtained by laminating the same, and an electronic circuit board using the laminate.
- Phenolic resin is a compound useful as a curing agent for epoxy resin for semiconductor encapsulation, and as a raw material, adhesive, molding material, and paint for epoxy resin, and has excellent electrical properties and heat resistance. It is widely used in fields such as electrical and electronic parts, structural materials, adhesives and paints due to its adhesiveness and moisture resistance.
- epoxy resin for sealing semiconductors has high purity, heat resistance, moisture resistance, adhesion, low viscosity for high filling, low dielectric properties, Various properties such as fast curing and flame retardancy are required.
- soldering process becomes hotter than before, and the chip and frame, which are the components of the IC, and the sealing material Fat, or
- Japanese Patent Application Laid-Open No. 2003-286392 discloses dibenzothio.
- a technique for improving the adhesion by adding phen to the epoxy composition and suppressing cracks occurring in the package during heating in the solder reflow process is shown.
- this compound is extremely poor in reactivity and has a boiling point as low as around 330 ° C, which causes problems in heat resistance and flame retardancy.
- JP-A-10-237060 discloses a technique in which polyhydric phenols obtained by polycondensation of hetero compound aldehydes and phenols improve adhesion and thereby prevent the peeling of the knocker. It is disclosed.
- the reactivity is very low and it is difficult to polymerize with a long reaction time.
- problems such as the slow curing rate of molded products and the reduction of mechanical strength.
- phenolic resin is a useful compound as a curing agent for epoxy resin for electronic circuit boards and a raw material for epoxy resin.
- the cured product has excellent electrical properties, heat resistance, adhesiveness, moisture resistance, etc., impregnated with phenol resin in a fiber base, and cured to make a matrix of fiber reinforced resin, for example, fiber reinforced resin laminate Plates are widely used in the field of electrical and electronic parts such as electrical insulation materials.
- a fiber reinforced resin board using phenol resin as a matrix is prepared by impregnating a fiber substrate with phenol resin varnish in which phenol resin is dissolved in an organic solvent and drying it to prepare a pre-preda as a semi-curing stage. And after laminating a predetermined number of this pre-preda, it can be manufactured by completely curing the resin.
- phenolic resin used in the production of such fiber-reinforced resin boards include resol-type phenolic resin, but fiber-reinforced resin boards using resol-type phenolic resin have low electrical insulation. In addition, the heat resistance is insufficient.
- Japanese Patent Laid-Open No. 73824 proposes a fiber reinforced resin board using various novolac-type phenolic resins as a matrix. However, the flame retardancy is insufficient, and it was necessary to add a brominated flame retardant to impart flame retardancy to the resin composition.
- the multilayer printed circuit board manufacturing method is based on a so-called build-up method in which an organic insulating film is alternately laminated on a conductor layer without using a glass cloth, which is disadvantageous for dielectric properties, instead of using a conventional laminating press.
- the development of multilayer wiring boards is actively underway.
- a rubber component is sometimes added to improve the adhesion between the insulating layer and the conductor layer.
- the rubber component remains in the insulating layer, the heat resistance and electrical properties are increased. It may cause deterioration of characteristics such as insulation characteristics. For this reason, it is required to improve the adhesion properties of the resin itself.
- the present invention provides excellent adhesion and flame retardancy in applications such as insulating materials for electrical and electronic parts such as semiconductor encapsulating materials, laminates such as printed wiring boards, adhesives, molding materials, and paints.
- An object of the present invention is to provide a modified phenolic resin capable of providing an epoxy resin having good properties, a method for producing the modified phenolic resin, and an epoxy resin composition using the phenolic resin as a curing agent. To do.
- the present invention improves heat resistance, flame retardancy, and adhesion in addition to electrical insulation required as an electrical / electronic material using a specific modified phenolic resin as a curing agent. It is an object of the present invention to provide a pre-preda, a laminated board, and an electronic circuit board in which a glass base material is impregnated with a cured epoxy resin composition.
- R 1 represents a linear, branched or cyclic hydrocarbon group having 1 to 8 carbon atoms
- o B represents a hydroxyl group or a halogen atom.
- the modified phenolic resin according to the present invention is
- Phenolic, naphthol and their derivative powers A side chain of an aromatic ring having a hydroxyl group of a phenolic resin which is an alternating copolymer of at least one selected phenolic compound and a compound having a divalent linking group Is substituted with a group represented by the general formula (11)!
- R 1 represents a straight, branched or cyclic hydrocarbon group having 1 to 8 carbon atoms
- R 1 represents a linear, branched or cyclic hydrocarbon group having 1 to 8 carbon atoms.
- R 2 represents a hydrogen atom, a halogen atom, a hydroxyl group, a phenyl group, a linear or branched or cyclic alkyl group or alkoxy group having 1 to 10 carbon atoms, which may be the same or different. good.
- the linking group A represents a hydrocarbon group having 1 to 20 carbon atoms.
- k, o, x and z are integers from 0 to 4
- m and y are integers from 0 to 3
- the total number of x, y and z is an integer from 1 to 11.
- the number of repeating units n represents an integer of 0-50.
- R 1 represents a linear, branched or cyclic hydrocarbon group having 1 to 8 carbon atoms
- R 2 represents a hydrogen atom, a halogen atom, a hydroxyl group, a phenyl group, a linear or branched or cyclic alkyl group or alkoxy group having 1 to 10 carbon atoms, which may be the same or different. good.
- the linking group A represents a hydrocarbon group having 1 to 20 carbon atoms.
- k, o, x and z are integers from 0 to 6
- m and y are integers from 0 to 5
- the total number of x, y and z is an integer from 1 to 17.
- the number of repeating units n represents an integer of 0-50.
- the linking group A of the modified phenolic resin described in [3] or [4] is selected from a methylene group, a xylylene group, a biphenyl-alkyl group, and a basic force represented by the general formula (41) It is characterized by at least one species.
- R 2 represents a hydrogen atom, a halogen atom, a hydroxyl group, a phenyl group, a carbon atom number of 1 to: a straight chain or branched or cyclic alkyl group or alkoxy group of L0, which may be the same.
- the linking group A represents a hydrocarbon group having 1 to 20 carbon atoms, k and o are integers of 0 to 4, m is an integer of 0 to 3, and the number of repeating units n is Indicates an integer from 0 to 50.
- R 1 represents a linear, branched or cyclic hydrocarbon group having 1 to 8 carbon atoms.
- B represents a hydroxyl group or a halogen atom.
- the method for producing the modified phenolic resin represented by the general formula (3-1) includes the phenolic resin represented by the general formula (7-1) and the compound represented by the general formula (6-1). Are reacted in the presence of an acid catalyst.
- R 2 represents a hydrogen atom, a halogen atom, a hydroxyl group, a phenyl group, a carbon atom number of 1 to: a straight chain or branched or cyclic alkyl group or alkoxy group of L0, which may be the same.
- the linking group A represents a hydrocarbon group having 1 to 20 carbon atoms, k and o are integers of 0 to 6, m is an integer of 0 to 5, and the number of repeating units n is Indicates an integer from 0 to 50.
- R 1 represents a linear, branched, or cyclic hydrocarbon group having 1 to 8 carbon atoms.
- B represents a hydroxyl group or a halogen atom.
- the epoxy resin composition according to the present invention comprises (A) a bifunctional or higher functional epoxy compound or a bifunctional or higher functional epoxy resin, (B) a curing agent, and (C) curing acceleration.
- An epoxy resin composition comprising an agent, wherein (B) the curing agent is the modified phenolic resin according to any one of [1] to [5].
- the epoxy resin composition according to [9] above is (D) organic and Z or inorganic filling Containing (A) a bifunctional or higher functional epoxy compound or a bifunctional or higher functional epoxy resin and (B) a total mass of 100 parts by mass of the curing agent, in a range of 100 to 1900 parts by mass. It is a feature.
- a cured epoxy resin composition according to the present invention is obtained by thermally curing the epoxy resin composition according to any one of [9] or [10].
- a pre-preda in which a glass substrate is impregnated with the epoxy resin composition of the present invention, a laminate obtained by laminating it, and an electronic circuit board using the same are provided by the following items.
- a pre-preda according to the present invention is an epoxy resin containing (A) a bifunctional or higher functional epoxy compound or a bifunctional or higher functional epoxy resin, (B) a curing agent, and (C) a curing accelerator.
- the (B) curing agent is a phenolic resin in which phenol, naphthol and derivatives thereof are alternating copolymers of at least one selected phenolic compound and a compound having a divalent linking group.
- a modified phenolic resin obtained by substituting a side chain of an aromatic ring having a hydroxyl group with a group represented by the general formula (11), wherein the epoxy resin composition is impregnated into the glass substrate. It is characterized by that.
- R1 represents a linear, branched or cyclic hydrocarbon group having 1 to 8 carbon atoms
- the curing agent is an alternating co-polymer of phenol, naphthol, and at least one phenolic compound selected from these derivatives and a compound having a divalent linking group. It is a phenolic resin that is a polymer, and is a modified phenolic resin in which the side chain of the aromatic ring having a hydroxyl group is substituted with a group represented by the general formula (12) .
- R 1 represents an alkylene group having 1 to 3 carbon atoms, a 1,4-cyclohexylene group, or a phenylene group.
- the curing agent is a modified phenolic resin represented by the general formula (2-2).
- R 1 represents an alkylene group having 1 to 3 carbon atoms, 1,4-cyclohexylene group, or phenylene group.
- R 2 represents a hydrogen atom, a fluorine atom, a chlorine atom, Represents a hydroxyl group, a phenyl group, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms, which may be the same or different.
- Repetitive unit number n represents an integer of 0 to 50
- the curing agent is a modified phenolic resin represented by the general formula (3-2).
- the linking group A is a methylene group, a xylylene group, a biphenylaralkyl group, or a group represented by the general formula (4-1). It is characterized by being a modified phenolic resin that is at least one selected.
- the prepreader according to any one of [1] to [5] above is characterized in that a glass substrate is impregnated with an epoxy resin composition having an epoxy equivalent of 170 to 100 Og / eq. To do.
- the pre-predder according to any one of [1] to [6] described above is based on (A) a bifunctional or higher functional epoxy compound or a bifunctional or higher functional epoxy resin (100 parts by weight).
- a glass substrate is impregnated with an epoxy resin composition having a weight of 2 to 150 parts by weight.
- a laminate according to the present invention is characterized in that the pre-preder according to any one of the above [1] to [7] is laminated.
- An electronic circuit board according to the present invention is characterized by using the laminated board described in [8] above.
- the modified phenolic resin of the present invention can exhibit excellent adhesion and flame retardancy when used as a curing agent for epoxy resin, and is extremely valuable industrially. Moreover, by using the modified phenolic resin of the present invention as a curing agent for epoxy resin, in addition to the electrical insulation required for electrical and electronic materials, heat resistance, flame retardancy, and adhesion are improved. In addition, a pre-preda in which a glass base material is impregnated with an epoxy resin composition, a laminate obtained by laminating the glass substrate, and an electronic circuit board using the laminate are provided.
- the modified phenolic resin according to the present invention a production method thereof, an epoxy resin composition containing the modified phenolic resin as a curing agent, and a cured product thereof will be specifically described.
- the modified phenolic resin of the present invention is an alternating copolymer of at least one phenolic compound selected from phenol, naphthol and derivatives thereof (hereinafter referred to as phenolic compound) and a compound having a divalent linking group.
- phenolic compound selected from phenol, naphthol and derivatives thereof
- R 1 represents a linear, branched or cyclic hydrocarbon group having 1 to 8 carbon atoms
- R 1 of the group represented by the general formula (1) include methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, otamethylene, ethethylene, 2-methyl- Tetramethylene, 2-methyl-hexamethylene, 2-ethyl-hexamethylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,4-cyclohexylene, 1,4-cyclooctylene, vinylene , Propenylene, butanediylidene, 1-propaninole-3-ylidene, 0-phenylene, m-phenylene, p-phenylene, 3-cyclohexene-1, 2-ylene, 2, 5- Examples thereof include cyclohexagen-1,4-ylene, and among these, methylene and ethylene are particularly preferable.
- the modified phenolic resin of the present invention has a sulfur atom of 0.01 to 2 monole, preferably 0.05 to L5 monole, with respect to 1 mol of hydroxyl group of the modified phenolic resin. 0.1 to 1 monole is preferable.
- the hydroxyl group content in the modified phenolic resin can be determined by, for example, titrating the acetic acid produced after decomposing the excess reagent with water using pyridine as a solvent and dehydrating the excess reagent with water.
- the sulfur atom content can be determined by a method such as NMR analysis using a chloroform solvent.
- Examples of such modified phenolic resin include compounds represented by the following general formula (2-1).
- R 1 represents a linear, branched or cyclic hydrocarbon group having 1 to 8 carbon atoms.
- R 2 represents a hydrogen atom, a halogen atom, a hydroxyl group, a hydrocarbon group, or a carbon atom number.
- the number of repeating units n is 0 to Indicates an integer of 50.
- R 1 represents a linear, branched or cyclic hydrocarbon group having 1 to 8 carbon atoms.
- R 2 represents a hydrogen atom, a halogen atom, a hydroxyl group, a phenyl group, or 1 carbon atom.
- O, x and z are integers from 0 to 6
- m and y are integers from 0 to 5
- the total number of x, y and z is an integer from 1 to 17.
- the number of repeating units n is 0 to Indicates an integer of 50.
- R 1 specifically, methylene, ethylene, trimethylene, tetramethylene, pentamethylene, Hexamethylene, heptamethylene, otatamethylene, ethynoleethylene, 2-methyleno-tetramethylene, 2-methyl-hexamethylene, 2-ethyl-hexamethylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1, 4- Cyclohexylene, 1,4-cyclooctylene, biylene, probel, butanediylidene, 1-prop-3-ylidene, o-phenylene, m-phenylene, p-phenylene , 3-cyclohexene-1,2-ylene, 2,5-cyclohexagen-1,4-ylene and the like, and among these, methylene and ethylene are particularly preferable.
- R 2 examples include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, noel, decyl, isopropyl, isobutyl, isopentyl, isohexyl, neopentyl, tert-butyl, tert -Pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, cyclodecyl, methoxy, ethoxy, propoxy, butoxy, phenoxy, isopropoxy, isobutoxy, sec-butoxy, te rt-butoxy, phenol, naphthyl, Antil, phenanthyl and the like can be mentioned, and among these, a hydrogen atom, a halogen atom, a hydroxyl group, methyl and me
- the linking group A may be a divalent compound. Specifically, methylene, ethylene , Trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, decamethylene, groups represented by general formula (4-1), 1,3-cyclobutylene, 1,4-cyclohexylene, 1,4-cyclooctylene, beylene, probel, butanediylidene, 1-prop-3-ylidene, o-phenylene, m-phenylene, p-phenylene, 3-cyclo Hexene-1,2-ylene, 2,5-cyclohexagen-1,4-ylylene, 1,2-xylylene, 1,3-xylylene, 1,4-xylylene, 1,2-xylylene-biphenyl 1, 3-xylylene-biphenyl, 1,4-xylylene-biphenyl, etc., among these, in order to
- X and z in the general formula (2-1) are preferably integers of 0 to 4, preferably 0 to 2, and more preferably 0 to 1.
- y is 0 to It is preferably an integer of 3, preferably an integer of 0 to 2, and more preferably an integer of 0 to 1.
- the total number of x, y and z is 1 to: an integer of L1, preferably an integer of 1 to 5, and more preferably an integer of 1 to 3.
- the number of repeating units n is preferably an integer of 0 to 50, more preferably an integer of 0 to 15.
- X and z in the general formula (3-1) are preferably integers of 0 to 6, preferably 0 to 3, and more preferably 0 to 1.
- y is 0 to It is preferably an integer of 5, preferably an integer of 0 to 2, and more preferably an integer of 0 to 1.
- the total number of x, y and z is an integer of 1 to 17, preferably an integer of 1 to 10, and more preferably an integer of 1 to 3.
- the repeating unit number n is preferably an integer of 0 to 50, more preferably an integer of 0 to 15.
- the modified phenolic resin of the present invention is a group in which the side chain of an aromatic ring having a hydroxyl group is represented by the general formula (11)
- R 1 represents a linear, branched, or cyclic hydrocarbon group having 1 to 8 carbon atoms.
- the adhesion and flame retardancy performance can be greatly improved without compromising the mechanical properties such as curability, glass transition temperature, hygroscopicity, and bending strength of fat and phenol aralkyl resin.
- the durable moisture resistance time is 100 to 130 hours for the modified phenol novolac resin of the present invention and 100 to 148 hours for the modified phenol dicyclopentagen resin of the present invention.
- flame retardancy is preferably Vl and further V-0 according to UL94 test evaluation criteria.
- modified phenolic resin having a specific structure represented by the general formula (2-1) or the general formula (3-1) of the present invention include the following chemical formulas (1) to (1): Shown in (20).
- x and z are integers of 0 to 4, y is an integer of 0 to 3, and the total number of x, y and z is 1 to: an integer of L 1; The number n represents an integer from 0 to 50.
- X and z are integers of 0 to 4
- y is an integer of 0 to 3
- the total number of x, y and z is 1 to: an integer of L 1.
- a repeating unit The number n represents an integer from 0 to 50.
- X and z are integers of 0 to 4
- y is an integer of 0 to 3
- the total number of x, y and z is 1 to: an integer of L 1.
- repeating units The number n represents an integer from 0 to 50.
- x and z are integers of 0 to 4
- y is an integer of 0 to 3
- the total number of x, y and z is 1 to: an integer of L 1.
- n represents an integer from 0 to 50.
- X and z are integers of 0 to 4
- y is an integer of 0 to 3
- the total number of x, y and z is 1 to: an integer of L 1.
- a repeating unit The number n represents an integer from 0 to 50.
- X and z are integers of 0 to 4
- y is an integer of 0 to 3
- the total number of x, y and z is 1 to: an integer of L 1.
- the number of repeating units n is Indicates an integer from 0 to 50.
- x and z are integers from 0 to 4
- y is an integer from 0 to 3
- the total number of x, y and z is an integer from 1 to 11.
- the number of repeating units n Represents an integer of 0 to 50.
- X and z are integers of 0 to 4
- y is an integer of 0 to 3
- the total number of x, y and z is 1 to: an integer of L 1.
- a repeating unit The number n represents an integer from 0 to 50.
- X and z are integers of 0 to 6
- y is an integer of 0 to 5
- the total number of x, y and z is an integer of 1 to 17.
- the number of repeating units n represents an integer of 0 to 50.
- the hydroxyl group and the group represented by the general formula (1) may be substituted at any position of the naphthalene ring.
- X and z are integers of 0 to 6
- y is an integer of 0 to 5
- the total number of x, y and z is an integer of 1 to 17.
- the number of repeating units n represents an integer of 0 to 50.
- the hydroxyl group and the group represented by the hydroxyl group and the general formula (11) may be substituted at any position of the naphthalene ring.
- x and z are integers of 0 to 6
- y is an integer of 0 to 5
- the total number of x, y and z is an integer of 1 to 17.
- the number of repeating units n represents an integer of 0 to 50.
- the hydroxyl group and the group represented by the general formula (11) may be substituted at any position of the naphthalene ring.
- X and z are integers of 0 to 6
- y is an integer of 0 to 5
- the total number of x, y and z is an integer of 1 to 17.
- the number of repeating units n represents an integer of 0 to 50.
- the hydroxyl group and the group represented by the general formula (11) may be substituted at any position of the naphthalene ring.
- the modified phenolic resin of the present invention comprises at least one kind of phenolic compound selected from phenol, naphthol and derivatives thereof and a compound having a divalent linking group.
- the side chain of the aromatic ring having a hydroxyl group of the phenol resin, which is a copolymer, has a structure substituted with a group represented by the general formula (11). It can be obtained by reacting the compound represented by the general formula (6-1) with an acid catalyst.
- R 1 represents a linear, branched or cyclic hydrocarbon group having 1 to 8 carbon atoms.
- B represents a hydroxyl group or a halogen atom.
- phenol resin which is an alternating copolymer with a compound, phenol resin represented by the following general formula (5-1):
- R 2 represents a hydrogen atom, a halogen atom, a hydroxyl group, a phenyl group, a carbon atom number of 1 to: a straight, branched or cyclic alkyl group or an alkoxy group of L0, which may be the same.
- the linking group A represents a hydrocarbon group having 1 to 20 carbon atoms, k and o are integers of 0 to 4, m is an integer of 0 to 3, and the number of repeating units n is It represents an integer of 0 to 50.
- . B represents a hydroxyl group or a halogen atom.
- the modified phenolic resin represented by the general formula (3-1) is composed of alternately co-polymerized phenol, naphthol and at least one kind of phenolic compound selected from these derivatives and a compound having a divalent linking group.
- Specific examples of the phenolic resin that is a coalescence include phenolic resin represented by the following general formula (7-1),
- R 2 represents a hydrogen atom, a halogen atom, a hydroxyl group, a phenyl group, a carbon atom number of 1 to: a straight chain, branched or cyclic alkyl group or alkoxy group of L0, which may be the same.
- the linking group A represents a hydrocarbon group having 1 to 20 carbon atoms, k and o are integers of 0 to 6, m is an integer of 0 to 5, and the number of repeating units n is It represents an integer of 0 to 50.
- phenol resin represented by the general formula (5-1) of the present invention include phenol novolak resin, phenol-dicyclopentagen resin, phenol aralkyl resin, and phenol bi-alkyl alcohol.
- examples of the phenol resin represented by the general formula (7-1) include naphthol aralkyl resin, and two or more kinds of resins can be used alone. It is acceptable to use enol sallow together.
- a phenol novolac resin reacts a phenol compound and formaldehyde in the presence of an acid catalyst. Obtained.
- the phenolic compounds used include phenol, 0-creso monore, m-creso monore, p-creso monore, 0-ethino leunore, m-ethino leenore, p-ethylenol and the like. is there.
- phenol-dicyclopentadiene rosin is obtained by reacting a phenol compound with dicyclopentadiene.
- the phenol compound used include phenol nore, 0-crezo monole, m- Cresol Monole, p-Crezo Monore, 0-Echinenolephenol, m-Echinenolephenol, ⁇ -Ethylphenol, pn-Propylphenol, p-Isopropylphenol, pn-Butinolevenole, ⁇ -sec-Buchi Norenoenore, p-tert-Butinoleunoenole, Otachilphenol, Norfenol, p-Cyclohexylphenol, 2, 4-xylenol, 2, 6-xylenol, 4, 6-xylenol, 3, 5-xylenol, 2,4,6-trimethylphenol, 2-methoxyphenol, 3-methoxyphenol, 4-methoxyphenol.
- the phenol aralkyl resin is obtained by reacting a phenol compound with an aralkyl halide, an aralkyl alcohol, or an aralkyl compound which is a derivative thereof.
- a phenol compound used include those similar to the case of phenol-dicyclopentagen rosin.
- Aralkyl compounds to be reacted with phenolic compounds include ⁇ , ⁇ '-dichloro- ⁇ -xylene, ⁇ , ⁇ ' -dichloro-m-xylene, ⁇ , ⁇ '-dichloro-mouth - ⁇ -xylene, ⁇ , ⁇ ' ⁇ , ⁇ '-Dihalogenoxylenes such as -dibromo- ⁇ -xylene, ⁇ , ⁇ ' -dibromo-m-xylene, ⁇ , ⁇ '-dibromo- ⁇ -xylene; ⁇ , ⁇ ' -dihydroxy- ⁇ -xylene Ex, ⁇ '-dihydroxy-m-xylene, ex, ⁇ '-dihydroxy-0-xylene Silylene glycols: ⁇ , ⁇ '-dimethoxy- ⁇ -xylene, ⁇ , ⁇ ' -dimethoxy-m-xylene,, ⁇ '-dime
- the phenol bialkylalkyl resin is obtained by reacting a phenol compound with biphenylalkylolide or a biphenylalkylalkyl compound which is a derivative thereof.
- phenol compound used include those similar to the case of phenol-dicyclopentagen rosin.
- Biphenylalkyl compounds reacted with phenolic compounds include 2,2'-bischloromethylbiphenyl, 2,3'-bischloromethylbiphenyl, 2,4'-bischloromethylbiphenyl, 3, 3'-bischloromethylbiphenyl, 3,4'-bischloromethylbiphenyl, 4,4'-bischloromethylbiphenyl, 2,2'-bisbromomethylbiphenyl, 2,3'-bisbromomethyl Dihalogeno such as biphenyl, 2,4'-bisbromomethylbiphenyl, 3,3'-bisbromomethylbiphenyl, 3,4'-bisbromomethylbiphenyl, 4,4 and bisbromomethylbiphenyl Examples include, but are not limited to, methyl biphenyls, and two or more bi-alkyl compounds may be used alone or in combination.
- naphthol aralkyl rosin can be obtained by reacting with aralkyl halide, aralkyl alcohol or a derivative thereof described in the method for producing ⁇ -naphthol, ⁇ -naphthol phenol aralkyl.
- R 2 represents a linear, branched or cyclic hydrocarbon group having 1 to 8 carbon atoms.
- B represents a hydroxyl group or a halogen atom.
- hydrocarbon group R 1 in the compound represented by the general formula (6-1) examples include methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, and otatamethylene.
- Ethylethylene, 2-methyl-tetramethylene, 2-methyl-hexamethylene, 2-ethyl-hexamethylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,4-cyclohexylene, 1, 4 -Cyclooctylene beylene, propylene, butanediylidene, 1-prop-3-ylidene.
- methylene and ethylene are preferable.
- B is a hydroxyl group or a halogen atom, and among the halogen atoms, a chlorine atom is particularly preferred.
- Specific examples of the compound represented by the general formula (6-1) include 2-thiophene methanol, 3-thiophene methanol, 2-thiophene ethanol, 3-thiophene ethanol, 2-thiophene propanol, 3 -Thiophene propanol, 2-thiophenebutanol, 3-thiophenbutanol, 2-thiophenpentanol, 3-thiophenpentanol, 2-thiophenhexanol, 3-thiophenhexanol, 2-thiophene Heptanol, 3-thiophene heptanol, 2-thiophenoctanol, 3-thiophenoctanol, 2-thiophencyclopropanol, 3-thiophencyclopropanol, 2-thiophencyclobutanol, 3- Thiophenecyclobutanol, 2-thiophencyclopentanol, 3-thiophene cyclonol, 2-thiophene cyclohexano 3-cyclohex
- the phenolic resin represented by the general formula (5-1) or the general formula (7-1) of the raw material and the compound represented by the general formula (6-1) in the container are further required as an acid catalyst. Charge the solvent accordingly.
- the compound represented by the general formula (6-1) can be charged in a solution state or without being dissolved in a solvent.
- the reaction solution is controlled at a predetermined temperature, and the reaction is carried out for a predetermined time with stirring while distilling off water and halide produced by the reaction. After a predetermined reaction time, if a solid catalyst is used, it is removed by filtration or the like.
- the modified phenolic resin of the present invention can be obtained by removing the solvent or the unreacted residual compound represented by the general formula (6-1) or precipitating the polymer by distillation under reduced pressure or the like. it can.
- the feed ratio of the phenolic resin represented by the general formula (5-1) or the general formula (7-1) and the compound represented by the general formula (6-1) as a raw material is
- the compound represented by the general formula (6-1) is used in an amount of 10 mmol to 6 mol, preferably 50 mmol to 4 mol, more preferably 100 mmol to 2 mol per mol of hydroxyl group equivalent in the resin. Is a mole.
- the acid catalyst used in the present invention includes inorganic acids such as hydrochloric acid, sulfuric acid and phosphoric acid, acetic acid, Solid acids such as organic acids such as oxalic acid, trifluoroacetic acid, P-toluenesulfonic acid, and jetyl sulfate, Lewis acids such as zinc chloride, aluminum chloride, iron chloride, and boron trifluoride, zeolite, montmorillonite, and activated clay Acid catalysts, super strong acids such as trifluoromethanesulfonic acid, acidic ion exchange resins such as alkane sulfonic acid type, and super strong acid ion exchange resins such as perfluoroalkane sulfonic acid type.
- P-toluenesulfonic acid or jetylsulfuric acid may be used in combination of two or more.
- the amount of the acid catalyst used may be a liquid such as an inorganic acid or an organic acid with respect to the total mass of phenol resin, the compound represented by the general formula (6-1), and the acid catalyst. It is 0.0001 to 10% by mass, preferably 0.001 to 5% by mass, and more preferably 0.01 to 1% by mass. In the case of a solid of a solid acid catalyst or an ion exchange resin, 1 to L00 mass%, preferably 10 to 50 mass%.
- the solvent can be used as necessary, and any solvent can be used as long as the object of the present invention is not impaired.
- aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, mesitylene, and azole, halogenated carbonization such as dichloromethane, 1,2-dichloroethane, and 1,1,2-trichloroethane.
- examples thereof include hydrogen solvents, hydrocarbon solvents such as hexane, heptane, octane, and cyclohexane, and ester solvents such as ethyl acetate, butyl acetate, and amyl acetate.
- the amount of solvent used is preferably 20 ml or less, preferably 10 ml or less, and more preferably 5 ml or less with respect to the raw material mortar resin lg.
- the atmosphere of the reaction system may be any of air, inert gas such as nitrogen, argon and helium, but nitrogen atmosphere is particularly preferred from the viewpoint of cost performance, which prevents phenol oxidation.
- the reaction temperature is 40 to 250 ° C, preferably 60 to 200 ° C, more preferably 80 to 160 ° C.
- the reaction pressure can be any of reduced pressure, normal pressure, and increased pressure, but the reaction temperature is In cases where the boiling point is higher than the boiling point, it is desirable to carry out the pressure reaction using a pressure-resistant reaction vessel.
- the reaction time varies depending on the reaction temperature, etc., and ranges from 25 to 25 hours. In reality, the disappearance of the compound represented by the general formula (6-1) is tracked by high performance liquid chromatography or gas chromatography. While preferring to determine the end point. [0125] [Epoxy resin composition]
- the epoxy resin composition of the present invention comprises (B) a curing agent containing, as an essential component, a modified phenolic resin represented by the general formula (2-1) or general formula (3-1) of the present invention as a curing agent.
- a bifunctional or higher functional epoxy compound or a bifunctional or higher functional epoxy resin has two or more epoxy groups in one molecule. All of them are contained and have epoxy groups obtained by oxidation of olefins, glycidyl etherification of hydroxyl groups, glycidyl amination of primary and secondary amines, glycidyl esterification of carboxylic acids, and the like.
- dihydroxybenzenes such as catechol, resorcin, and hydroquinone
- 2,6-dihydroxynaphthalene 2,2-bis (4-hydroxyphenol) propane (bisphenol A), 2- (3-hydroxyphenol) -2- (4'-hydroxyphenol) ) Propane, bis (4-hydroxyphenol) methane (bisphenol F), bis (4-hydroxyphenol) sulfone (bisphenol S), bis (4-hydroxyphenol) sulfide, bis (4- Hydroxyphenyl) methylcyclohexane, bis (4-hydroxyphenyl) methylbenzene, 4,4 and dihydroxybiphenyl, 4,4'-dihydroxy-2,2'6,6'-tetramethylbiphenyl, 4 , 4 dihydroxydiphenyl ether, 6, 6'-dihydroxy-3, 3, 3 ', 3 tetramethyl-1, 1-spiroidane, 1, 3, 3-trimethyl-1- (4-hydroxyphenyl) Bisphenols such as 1-indane-6-ol; tetraphenol-roleethane, Oligophenols such as naphthol-cresol resol con
- R 1 represents a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 9 carbon atoms.
- the number of repeating units n represents an integer of 0 to 50, and the average is 0 to 15
- Aminophenols such as methane; epoxides of hydroxycarboxylic acids such as phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, dimer acid, 1,3 benzoic acid, etc.
- phthalic acid isophthalic acid, terephthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, dimer acid, 1,3 benzoic acid, etc.
- Glycidyl of these compounds having active hydrogen can be carried out by a known method, and it is most common to react epichlorohydrin in the presence of a hydrogen halide acceptor.
- metal catalysts especially T1NO
- the method of reacting with one is preferred, and it is also known.
- bifunctional or higher functional epoxy compounds or bifunctional or higher functional epoxy resins may be used alone or in combination of two or more.
- the epoxy resin composition used in the present invention is characterized by using the modified phenol resin of the present invention as an essential component as (B) a curing agent, and may be used alone or in combination of two or more.
- the modified phenolic resin used as a curing agent is arranged so that the hydroxyl equivalent of (B) curing agent is in the range of 0.5 to 1.2 equivalents with respect to 1 equivalent of epoxy equivalent of epoxy resin. Furthermore, it is preferable to be blended in a range of 0.75 to: L 1 equivalent.
- the present invention is preferable because (B) a modified phenolic resin used as a curing agent is blended so as to be in the above range, and a cured product excellent in both flame retardancy and adhesion can be obtained.
- the (C) curing accelerator used in the present invention is not particularly limited as long as it accelerates the curing reaction of epoxy resin and phenolic compound or resin.
- Curing accelerators used at this time include tributylphosphine, triphenylphosphine, tris (dimethoxyphenylphosphine), tris (hydroxypropyl) phosphine, tris (cyanoethyl) phosphine, tris (trimethoxyphenyl) phosphine, Tris (dimethoxyphenyl) phosphine Phosphines such as tris (trimethylphenol) phosphine and tris (dimethylphenol) phosphine; Phosphomumates such as phospho-tetraphenyl; 2-methylimidazole, 2-phenolimidazole, 2-ethyl-4-methylimidazole, 2-undecylimidazole, 1-cyanethyl-2-methylimid Zole, 2,4-Dis
- curing accelerators may be used alone or in admixture of two or more.
- organic and / or inorganic fillers and other additives can be used as necessary.
- organic and Z or inorganic fillers are used to improve the mechanical properties and reduce the overall cost, and colorants such as carbon black are used to prevent malfunction due to light.
- the amount of organic and Z or inorganic filler used is (A) a bifunctional or higher functional epoxy compound or a bifunctional or higher functional epoxy resin and (B) a total mass of 100 parts by mass of the curing agent. It is the range of 100-1900 mass parts, Preferably it is 250-1900 mass parts, More preferably, it is 550-1900 mass parts or more.
- Organic and Z or inorganic fillers used include silica, alumina, silicon nitride, carbonized carbide, talc, calcium silicate, calcium carbonate, my strength, clay, titanium white powder, glass fiber, carbon fiber And fiber bodies such as aramid fibers.
- crystalline silica and Z or fused silica are preferred for use as a sealing material, and the shape is spherical or spherical considering the fluidity during molding of the resin composition. Spherical or a mixture of spherical and crushed is desirable.
- Coupling agents that are desirable are silane, titanate, aluminate, or zircoaluminum. Examples thereof include nates.
- a silane coupling agent is preferable, and a silane coupling agent having a functional group that reacts with an epoxy group is particularly preferable.
- Examples of such coupling agents include vinyltrimethoxysilane and butyltriethoxysilane. N- (2-aminomethyl) -3-aminominomethyldimethoxysilane, N- (2-aminoethyl) -3-aminominotrimethoxysilane, 3-aminopropyltriethoxysilane, 3-anilinop Examples include pyrtriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxyplan, 3-methacryloxypropyltrimethoxysilane, and 3-mercaptopropyltrimethoxysilane. These can be used alone or in combination of two or more. It is desirable that these coupling agents are previously adsorbed on the surface of the inorganic filler or fixed by reaction.
- the epoxy resin cured product of the present invention is a cured product obtained by thermosetting the epoxy resin composition of the present invention.
- the curing temperature is 100 ° C to 220 ° C, more preferably 150 ° C to 200 ° C, and the curing time is 1 minute to 20 hours, more preferably 1 hour to 10 hours.
- the epoxy resin composition of the present invention having excellent adhesion and flame retardancy can be obtained by thermosetting the epoxy resin composition.
- the semiconductor device of the present invention is obtained by sealing a semiconductor integrated circuit using the epoxy resin composition of the present invention.
- a method for manufacturing a semiconductor device other methods such as injection molding, compression molding, and casting molding, which are the most common methods using low-pressure transfer molding, are possible.
- a special method using a solvent is also possible.
- the pre-preder according to the present invention a laminated board formed by laminating it, and an electronic circuit board obtained by using this laminated board will be specifically described.
- the epoxy resin composition used in the prepreader of the present invention includes the following (A) a bifunctional or higher functional epoxy compound or a bifunctional or higher functional epoxy resin, (B) a curing agent, and (C) Contains a curing accelerator.
- a bifunctional or higher functional epoxy compound or a bifunctional or higher functional epoxy Fats include all those having two or more epoxy groups in one molecule, oxidation of olefins, glycidyl etherification of hydroxyl groups, glycidyl amination of primary and secondary amines, glycidyl esters of carboxylic acids I) Epoxy compound or raw material for epoxy effect
- hydroxyl groups used for glycidyl etherification of hydroxyl groups include dihydroxybenzenes such as force techol, resorcin, hydroquinone; 2,6-dihydroxycinaphthalene, 2,2-bis (4-hydroxyphenol).
- phenol aralkyl resins such as phenol aralkyl resins, biphenyl aralkyl resins and naphthol aralkyl resins.
- amino groups used in glycidylamines of primary and secondary amines include ethylenediamine, propylenediamine, hexamethylenediamine, aniline, 4,4 and diaminodiphenylmethane (MDA).
- carboxyl groups used for glycidyl esterification of carboxylic acids include phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, dimer acid, and 1,3 benzoic acid.
- Examples include epoxidized hydroxycarboxylic acids.
- Glycidylation of the above-mentioned compounds having active hydrogen such as hydroxyl group, amino group and carboxyl group can be carried out by a known method, and it is most common to react epichlorohydrin in the presence of a hydrogen halide acceptor. Is.
- metal catalysts especially thallium compounds such as T1NO and TKOCOCF are used as catalysts.
- the bifunctional or higher functional epoxy compound or bifunctional or higher epoxy resin obtained from the above compound may be used alone or in combination of two or more, or an epoxy compound and an epoxy resin may be used in combination. In addition, when used in combination, they may be used at an arbitrary ratio.
- the (B) hardener used in the present invention is an alternating copolymer of phenol, naphthol and at least one phenolic compound selected from these derivatives and a compound having a divalent linking group.
- the modified phenolic resin include a certain type of phenolic resin and a substitutional introduction of a side chain of an aromatic ring having a hydroxyl group in which the resinous resin is present with the group represented by the general formula (11).
- it is an alternating copolymer of phenol, naphthol, and derivatives thereof at least one kind of selected phenol compound and a compound having a divalent linking group.
- This is a modified phenolic resin that is substituted with a group represented by the following general formula (12) on the side chain of an aromatic ring having a hydroxyl group in which the resin is present.
- R 1 represents an alkylene group having 1 to 3 carbon atoms, a 1,4-cyclohexylene group, or a phenylene group.
- phenol compounds to be used include phenol, 0-cresol, m-tale zonore, p-creso mononore, 0-ethino leuenore, m-ethino leuenore, p-ethino leuenol, pn -Propylphenol, p-isopropylphenol, 2,4-xylenol, 2,6-xylenol, 4,6-xylenol, 3,5-xylenol, 2,4,6-trimethylphenol, o-phenol-phenol, m-Hue-Nolehuenore, p-Hue-Nolehuenore, o-Black mouth Phenol, m-Black mouth Phenol, p-Black mouth Phenol, o-Phenololeophenol, m-Funoleophenol, p-Fluorophenol, o- Dihydroxybenzene, m-di
- phenol, 0-cresol, m-cresol, p-cresol, ⁇ -naphthol, and j8-naphthol preferred are phenol and a-naphthol.
- the linking group A includes a methylene group, an ethylene group, a propylene group, an isopropylene group, a 1,3-cyclopentylene group, a 1,4-cyclohexylene group, a 1,4-cyclooctylene group, a 0-phenol.
- Dilene group, m-phenylene group, p-phenylene group, 1,2-xylylene group, 1,3-xylylene group, 1,4-xylylene group, 1,2-xylylene-biphenyl group Examples include 1,3-xylylene-biphenyl group, 1,4-xylylene-biphenyl group, and the above general formula (4-1).
- methylene group, 1,2-xylylene group, 1,3-xylylene group, 1,4-xylylene group, 1,2-xylylene-biphenyl group, 1,3-xylylene-biphenyl group, 1 , 4-Xylylene-biphenyl group, the above general formula (4-1) is preferable.
- a methylene group, an ethylene group, an m-phenylene group, a p-phenylene group, a 1,3-xylylene-biphenyl group, a 1,4-xylylene-biphenyl group, the above general formula (4— 1) is preferred.
- the raw material compound to be the linking group A include 1) formaldehyde for phenol novolac resin, 2) dicyclopentagen for phenol-dicyclopentadiene resin, and 3) phenol.
- the aralkyl resin includes aralkyl compounds ⁇ , ⁇ and dichloro- ⁇ -xylene, ⁇ , ⁇ '-dichloro-m-xylene, ⁇ , ⁇ ' -dichloro- ⁇ -xylene,, ⁇ '-dibromo-p - xylene, alpha, alpha '- dibromo - m-xylene, alpha, alpha' - dibromo - o-alpha, such as xylene, alpha '- dihalogeno xylenes; alpha, alpha' - dihydroxy - .rho.
- xylene alpha, a '-Dihydroxy-m-xylene, xylylene glycols of ⁇ , ⁇ '-dihydroxy-o-xylene; ⁇ , ⁇ '-dimethoxy- ⁇ -xylene, ⁇ , ⁇ '-dimethoxy-m-xylene, ⁇ , ⁇ ' -Dimethoxy-0-xylene, ⁇ , ⁇ '-diethoxy- ⁇ -xyle , ⁇ , ⁇ '-diethoxy-m-xylene, ⁇ , ⁇ ' -diethoxy- ⁇ -xylene, ⁇ , ⁇ '-dipropoxy- ⁇ -xylene, ⁇ , ⁇ ' -dipropoxy-m-xylene, ⁇ , ⁇ ' -Dipropoxy- ⁇ -xylene, ⁇ , ⁇ ' -diisopropoxy- ⁇ -xylene, ⁇ , ⁇ ' -diisopropoxy -m-x
- Phenolic bialkyl alcohols include 2,2'-bischloromethyl, which is a bialkylalkyl halide or a biphenylalkyl compound thereof. Rubiphenyl, 2,3'-bischloromethylbiphenyl, 2,4'-bischloromethylbiphenyl, 3,3'-bischloromethylbiphenyl, 3,4'-bischloromethylbiphenyl 4, 4 and bischloromethyl biphenyl, 2, 2 and bisbromomethyl biphenyl, 2, 3 and bisbromomethyl biphenyl, 2, 4'-bisbromomethyl biphenyl, 3, And dihalogenomethyl biphenyls such as 3'-bisbromomethylbiphenyl, 3,4'-bisbromomethylbiphenyl, 4,4'-bisbromomethylbiphenyl, etc. All the raw materials described in 1) to 5) above can be used.
- phenolic biphenyl aralkyl resin 3, 3'-bischloromethyl biphenyl, 4, 4'-bis Chloromethyl biphenyl
- Naphthol aralkyl rosin includes formaldehyde, dicyclopentagen, ⁇ , ⁇ '-dichloro- ⁇ -xylene, 3,3'-bischloromethyl biphenyl, 4 , 4'-bisqueromethyl biphenyl.
- An alternating copolymer that is, a phenolic resin
- a condensation reaction using the above phenol compound and the above raw material that becomes the divalent linking group A.
- the manufacturing method is not particularly limited, and all known methods can be applied. Specifically, phenols, linking groups, and an acid catalyst are charged and reacted for several hours while maintaining the reaction temperature at 80 to 150 ° C. to obtain crude phenol resin. Further, the phenol resin purified by dephenolization at 150 ° C or higher under reduced pressure is obtained. iv) Raw material of side chain of modified phenolic resin
- R 1 which is a divalent group of the general formula (12) are methylene group, ethylene group, propylene group, isopropylene group, 1,4-cyclohexylene group, and phenylene group. They are preferably a methylene group and an ethylene group.
- Specific examples of the raw material compound represented by the general formula (12) used for introducing the general formula (12) which is a side chain and a monovalent group include 2-thiophenmethanol, 3-thiophene Phenmethanol, 2-thiopheneethanol, 3-thiopheneethanol, 2-thiophenepropanol, 3-thiophenepropanol, 2-thiophenecyclohexanol, 3-cyclohexanol, 2- Thiophenecyclootathanol, 3-thiophencyclooctanol, 1- (2-Cenyl) -2-propanol, 1- (3-Chel) -2-propanol, 2-Chloromethylthiophene, 3 -Chloromethinorethiophene, 2-chloroethinorethiophene, 3-chloroethinorethiophene, 2-bromomethinorethiophene, 3-bromomethinorethiophene, 2-bromoeth
- 2-thiophene methanol, 3-thiophene methanol, 2-chloromethylthiophene, 3-chloromethylthiophene, 2-bromomethylthiophene, 3-bromomethylthiophene, 2-fluoromethylthiophene, 3-fluoromethylthiophene, 2 -Yoodomethylthiophene and 3-odomethylthiophene are preferred in terms of flame retardancy.
- the compound of the formula (12) is represented by the general formula (12) as the side chain of phenolic resin.
- the method for introducing a monovalent group that is, the method for modifying phenolic resin is not particularly limited, and all known methods can be applied.
- the phenolic resin and the raw material compound represented by the general formula (1-2) are in a solution state or suspended in the presence of an acid catalyst, using a solvent as necessary.
- the reaction is carried out while distilling off the water and halides produced in the reaction.
- the atmosphere of the reaction system is preferably in air or an inert gas such as nitrogen, argon, or helium.
- the reaction temperature is 40 to 250 ° C, preferably 60 to 200 ° C, more preferably 80 to 160 ° C, and the reaction time is actually traced by high performance liquid chromatography or gas chromatography while the end point is reached. Generally, it is in the range of 1 to 25 hours.
- the phenol resin and the raw material mixture of general formula (1-2) and the charging ratio are
- the raw material mixture of general formula (1-2) per 1 mol of hydroxyl equivalent value in fat is 10 mmol to 6 mol, preferably 50 mmol to 4 mol, more preferably 100 mmol to 2 mol.
- the acid catalyst used include inorganic acids such as acid, sulfuric acid, and phosphoric acid, organic acids such as acetic acid, oxalic acid, trifluoroacetic acid, P-toluenesulfonic acid, and jetylsulfuric acid, zinc chloride, and aluminum chloride.
- Lewis acid such as iron chloride and boron trifluoride
- solid acid catalyst such as zeolite, montmorillonite, activated clay
- super strong acid such as trifluoromethanesulfonic acid
- acidic ion exchange resin such as alkanesulphonic acid type
- perful Examples include superalkanesulfonic acid type super strong acid ion exchange resin, and P-toluenesulfonic acid and jetylsulfuric acid, which may be used alone or in combination of two or more, are preferred.
- the amount of the acid catalyst used is 0 for a liquid such as an inorganic acid or an organic acid with respect to the total mass of the phenol resin, the compound represented by the general formula (6-1), and the acid catalyst.
- the amount is from 0001 to 10% by mass, preferably from 0.001 to 5% by mass, more preferably from 0.01 to 1% by mass.
- solid acid catalyst or ion exchange resin solid it is 1 to 100% by mass, preferably 10 to 50% by mass.
- the modified phenolic resin has the excellent heat resistance, flame retardancy and adhesion properties of the present invention by introducing a monovalent group represented by the general formula (12) as the side chain of the phenolic resin. .
- mechanical properties such as flexural strength and flexural modulus have the same hygroscopic properties without compromising the performance of the phenolic resin before modification.
- the hydroxyl group content in the modified phenolic resin of the present invention is, for example, acetylated with acetic anhydride using pyridine as a solvent, and acetic acid produced after decomposition of the excess reagent with water. It can be determined by titrating with a potassium solution. It also contains sulfur atoms. The amount can be obtained by a method such as NMR analysis in a chloroform solvent.
- the hydroxyl group equivalent of the modified phenolic resin is 101-440 g / eq, preferably 105-400 g / eq, more preferably 110-350 g / eq. eq.
- the modified phenolic resin preferably has the above general formula (2-2) or general formula (3-2).
- R 2 which is a monovalent substituent, specifically, a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a methoxy group, An ethoxy group, a propoxy group, an isopropoxy group, a phenol group, a fluorine atom, a chlorine atom, a hydroxyl group and the like can be mentioned.
- a hydrogen atom, a hydroxyl group, a methyl group and a methoxy group are particularly preferable.
- These monovalent substituents R 2 are determined by the structure of the phenolic compound that is the raw material of the above phenol resin.
- X and z in the general formula (2-2) are integers of 0 to 4, preferably 0 to 2, more preferably 0 to 1.
- y is an integer of 0 to 3
- y is an integer of 0 to 2
- the total number of x, y and z is 1 to: an integer of L1, preferably an integer of 1 to 5, and more preferably an integer of 1 to 3.
- the number of repeating units n is preferably an integer of 0 to 50, and more preferably an integer of 0 to 15. Particularly preferred is an integer of 2 to 10.
- X and z in the general formula (3-2) are integers of 0 to 6, preferably 0 to 3, more preferably 0 to 1.
- y is an integer of 0 to 5
- y is an integer of 0 to 2
- the total number of x, y and z is an integer of 1 to 17, preferably an integer of 1 to 10, and more preferably an integer of 1 to 3.
- the number of repeating units n is preferably an integer of 0 to 50, and more preferably an integer of 0 to 15. Most preferably, n does not have a certain range and is a compound, a polymer, or a mixture thereof.
- the number of repeating units n is preferably an integer of 0 to 50, more preferably 0 to 15. Further, the number of repeating units n is preferably an integer of 0 to 15, more preferably an integer of 0 to 15. Particularly preferred is an integer of 2 to 10. n must have a certain range and be a compound, polymer, or a mixture thereof. Most preferred.
- the amount of the curing agent (B), which is a modified phenolic resin, ranges from 2 to 150 parts by weight with respect to 100 parts by weight of (A) a bifunctional or higher functional epoxy compound or a bifunctional or higher functional epoxy resin. Is more preferably 20 to 140 parts by weight, particularly preferably 40 to 130 parts by weight, and most preferably 70 to 120 parts by weight.
- (B) When the amount of the curing agent used is less than 2 parts by weight, (A) The flame retardancy decreases due to an increase in the bifunctional or higher functional epoxy compound or the bifunctional or higher functional epoxy resin, or the effect of the present invention The adhesion which is is not obtained. On the other hand, when the amount used exceeds 150 parts by weight, problems such as a decrease in Tg of the cured product and a decrease in mechanical strength occur.
- the (C) curing accelerator used in the present invention is not particularly limited as long as it accelerates the curing reaction of epoxy resin and phenolic resin or resin.
- Specific examples of the curing accelerator include: Tributylphosphine, triphenylphosphine, tris (dimethoxyphenylphosphine), tris (hydroxypropyl) phosphine, tris (cyanoethyl) phosphine, tris (trimethoxyphenyl) phosphine, tris (dimethoxyphenyl) phosphinetris (tri Phosphines such as limethylphenol) phosphine and tris (dimethylphenyl) phosphine; 2-methylimidazole, 2-phenylimidazole, 2-ethyl-4-methylimidazole, 2-undecylimidazole, 1-cyanethyl-2-methylimidazole, 2,4-disiano-6- [2 -Imidazolyl
- (C) curing accelerators may be used alone or in combination of two or more.
- the amount used is 0.1 to 7% by weight, more preferably 0 to the total weight of (A) bifunctional or higher functional epoxy compound or bifunctional or higher epoxy resin and (B) curing agent. 3 to 5% by weight. Particularly preferred is 0.5 to 3% by weight, with 0.8 to 2% being most preferred.
- the epoxy resin composition of the present invention comprises (A) a bifunctional or higher functional epoxy compound or a bifunctional or higher functional epoxy resin, (B) a curing agent, and (C) a curing accelerator.
- any known method without particular limitation can be applied. Specifically, (A) a bifunctional or higher functional epoxy compound or a bifunctional or higher functional epoxy resin, (B) a curing agent, and (C) a curing accelerator are mixed with a pulverizer such as a Henshur mixer for several minutes. Take several hours to dry blend and mix. The mixed powder is weighed together with a solvent in a separable flask or the like, and dissolved at room temperature using a stirrer or the like to prepare an epoxy resin composition varnish. Epoxy rosin composition varnish recrystallizes with longer storage times. Alternatively, problems such as changes in physical properties may occur, so avoid long-term storage in varnish. It ’s better.
- a pulverizer such as a Henshur mixer
- the epoxy equivalent is preferably a bifunctional or higher functional epoxy compound or a bifunctional or higher functional epoxy resin having a range of 170 to 1000 gZeq. More preferably, the epoxy equivalent force is in the range of Sl 80 to 600 g / eq, and more preferably in the range of 200 to 400 g / eq.
- Eho 0 key sheet equivalent is less than 170, an increase in the water absorption of the cured product, a decrease in heat resistance after moisture absorption leads.
- it is higher than lOOOOg / eq, the impregnation property and solubility are deteriorated, and the Tg of the cured product is lowered to affect the heat resistance.
- (B) The curing agent is blended in such a way that (A) the epoxy equivalent of bifunctional or higher epoxy compound or epoxy functional of bifunctional or higher epoxy resin is equivalent to 1 equivalent, and the hydroxyl equivalent of (B) curing agent is 0.3. It is preferable to be blended so as to be in the range of ⁇ 1.5 equivalents, and it is preferable to blend so as to be in the range of 0.6 to 1.2 equivalents. When the blending is in the above range, a cured product excellent in both flame retardancy and adhesion is obtained, which is preferable.
- the amount of (C) curing accelerator used relative to the total weight of fat and (B) curing agent is as described above.
- organic fillers and inorganic fillers that can be added to the epoxy resin composition as needed.
- organic fillers include powder epoxy resin (for example, TEPIC)
- inorganic filler include magnesium oxide, calcium carbonate, zirconium silicate, zirconium oxide, calcium silicate, aluminum hydroxide, melamine resin, benzoguanamine resin, urea resin, cross-linked acrylic polymer, etc.
- calcium carbonate is particularly preferred because it can facilitate surface roughness when used as an insulating layer and can increase the adhesive strength with the conductor. [Prepredas, laminates, and electronic circuit boards]
- the pre-preda, laminate and electronic circuit board of the present invention are obtained by forming a layer comprising an epoxy resin composition and a glass substrate on at least one surface of a metal layer on which a copper foil or wiring layer is formed. It is.
- All the methods for producing the pre-preda, the laminate and the electronic circuit board of the present invention can be carried out according to a known method and is not particularly limited. Specifically, the epoxy resin composition of the present invention is dissolved in a solvent to prepare a varnish having a rosin content of 30 to 70 wt%, converted into a varnish, and glass substrate such as glass woven fabric or glass nonwoven fabric. The material is impregnated and dried at 120 to 180 ° C. and 80 to 250 ° C. to obtain a pre-preda. In the case of impregnation or drying, it can be performed under reduced pressure for the purpose of defoaming or increasing the drying speed.
- a woven fabric other than glass may be used as a non-woven fabric or the like, or a woven fabric made of glass may be used in combination with the non-woven fabric.
- the necessary number of the prepregs thus obtained are stacked and heated and pressed to obtain a laminate.
- an electronic circuit board is obtained by combining a laminated board and copper foil and heating and pressurizing.
- the epoxy resin composition is subjected to heat treatment, and any known method without particular limitation can be applied. Specifically, using a general-purpose pressure press, etc., the temperature is 150 to 250 ° C, the heating time is 1 minute to 10 hours, the pressure is 0 to 3 MPa. For the purpose of preventing oxidation and coloring, it can be carried out in an inert gas atmosphere such as nitrogen, helium or argon, in an air flow, or under reduced pressure.
- an inert gas atmosphere such as nitrogen, helium or argon
- the glass substrate such as a glass woven fabric and a glass nonwoven fabric used in the above production method
- a commercially available product that is always available and can be used is particularly limited.
- a method of obtaining an electronic circuit board at the same time by superimposing copper foils at the same time, a varnish or paste of epoxy resin composition, a metal such as copper A method of applying to a foil, a method of bonding an epoxy resin composition into a sheet or film form, and then bonding to a metal foil such as copper can also be applied.
- Aromatic hydrocarbons such as toluene and xylene, cellosol Cellosolves such as butyl and butyl citrate sorb, carbitols such as carbitol and butyl carbitol, and acetates such as ethyl acetate, butyl acetate, cellosolv acetate, and butyl catechol sorbate.
- ketones such as methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone.
- Aromatic hydrocarbons such as toluene and xylene
- cellosol Cellosolves such as butyl and butyl citrate sorb
- carbitols
- Epoxy resin composition 14 5 parts by mass (catalyst 2 parts by mass is counted as an external number, so the total number is 102 parts by mass), waxes 0.5 parts by mass (carnauba and Hoechst E), spherical silica 87 parts by mass Part (YXK-35R, manufactured by Tatsumori Co., Ltd.), and B stage was performed at 100 ° C for 3 minutes with superheated kneading with a roll. The obtained compound was filled in a mold and held at 175 ° C. for 200 seconds. After transfer molding, post-curing was performed at 175 ° C for 8 hours in an inert oven in a nitrogen atmosphere. Using the obtained specimen, the flexural modulus was measured in accordance with JIS K-6911.
- Epoxy resin composition 14 5 parts by mass (catalyst 2 parts by mass is counted as an external number, so the total number is 102 parts by mass), waxes 0.5 parts by mass (carnauba and Hoechst E), spherical silica 87 parts by mass Part (YXK-35R, manufactured by Tatsumori Co., Ltd.), and B stage was performed at 100 ° C for 3 minutes with superheated kneading with a roll. The obtained compound was filled in a mold and held at 175 ° CX for 200 seconds. After transfer molding, post-curing was performed at 175 ° C for 8 hours in an inert oven in a nitrogen atmosphere. The bending strength was measured according to JIS K-6911 using the obtained test piece.
- the moisture absorption rate was calculated based on the following equation by measuring the mass before and after absorbing moisture for 168 hours in an atmosphere of temperature 85 ° C and humidity 85%.
- the compound obtained at the time of making the test piece for bending elastic modulus was filled in a mold, held at 175 ° C for 200 seconds, and a package with a length of 20mm x width 20mm x thickness 1.75mm was manufactured using a transfer molding machine. Next, after curing at 175 ° C for 8 hours in an inert oven in a nitrogen atmosphere, leave it in an atmosphere of 85 ° C and 85% humidity to absorb moisture. At 72 hours, 96 hours, and 168 hours, 5 packages each time were extracted from the hygroscopic atmosphere, placed in a reflow oven, and held at 250 ° C for 10 seconds. Next, the knockout was taken out and cooled to room temperature, and the adhesion between the resin and the frame was observed with an ultrasonic microscope for the five packages to check for cracks and peeling. Next, the durable moisture resistance time was calculated based on the following formula.
- Endurance time (hours) 24 X (Sl / 5) +48 X (S2 / 5) + 72 X (S3 / 5) + 96 X (S4 / 5) + 168 X (S5 / 5)
- SI Number of packages that have not cracked or peeled after 24 hours of moisture absorption
- S2 Number of packages that have not cracked or peeled after 48 hours of moisture absorption
- S3 Cracked or peeled after 72 hours of moisture absorption
- S5 Number of packages that have not cracked or peeled after 168 hours of moisture absorption [Hydroxyl resin contains hydroxyl groups] amount]
- the hydroxyl group content in phenolic resin was determined by acetylating with pyridine as a solvent, acetic anhydride, and titrating the acetic acid produced after decomposition of the excess reagent with water with a potassium hydroxide solution.
- the content of sulfur atoms in phenolic resin was determined by a method based on elemental analysis such as NMR analysis and IR analysis using a chloroform solvent.
- the polyhydric phenol resin described in Japanese Patent Application Laid-Open No. 10-237060 was synthesized. Phenols (manufactured by Tokyo Chemical Industry Co., Ltd.) 94. lg (lmol), methanol (manufactured by Tokyo Chemical Industry Co., Ltd.) 50 g, sodium hydroxide (manufactured by Tokyo Chemical Industry Co., Ltd.) 10 g (0.25 mol) Weighed, thermometer, dropping funnel, Dean-Stark moisture separator, reflux condenser, nitrogen inlet tube and glass reactor equipped with stirrer, and raised the external temperature to 100 ° C under nitrogen flow When the phenol was dissolved and homogeneously refluxed, 2-thiophenecarboxaldehyde aldehyde (manufactured by Tokyo Chemical Industry Co., Ltd.) 56.lg (0.5 mol) was added dropwise over 2 hours, and the reaction was continued for 50 hours.
- the reaction was performed under the same conditions as in Synthesis Example 1 except that the reaction time was changed to 3 hours. Analyzed by gel permeation chromatography and gas chromatography in the same manner as in Synthesis Example 1, and confirmed that 2-thiophene methanol does not exist in the system, then modified phenolic salt represented by chemical formula (9) The fat was discharged into a SUS vat.
- the modified phenol novolak resin of Synthesis Example 1 (hydroxyl equivalent: 155 gZeq) 44.5 g (0.29 g equivalent) and trifluorophosphine 2 g (2%) as a curing accelerator were melt-mixed at 140 ° C for 10 minutes. After cooling to 100 ° C, 55.5 g (0. 5 g) of biphenol type epoxy resin (trade name: YX4000H, manufactured by Japan Epoxy Resin Co., Ltd.), epoxy equivalent 193 g / eq) as epoxy resin. 29 g equivalent) was added. The mixture was melted and kneaded at 100 ° C for 5 minutes to obtain a uniform resin composition.
- the evaluation results of the gel time and glass transition temperature (Tg) of this epoxy resin composition are shown in Table 1.
- the Table 1 shows the results of evaluating the flexural modulus, flexural strength, moisture absorption, flame retardancy, and reflow resistance of the cured epoxy resin composition.
- Phenolic novolac resin (trade name: PSM4261, manufactured by Gunei Chemical Industry Co., Ltd., hydroxyl equivalent 107gZeq) 35.7g (0.33g equivalent) as a curing agent and biphenol type epoxy resin (trade name: epoxy resin)
- YX4000H manufactured by Japan Epoxy Resin Co., Ltd.
- epoxy equivalent (193 g / eq) were replaced with 64.3 g (0.33 g equivalent).
- Table 2 The results are shown in Table 2.
- Phenolic dicyclopentadiene resin as a curing agent (trade name: DPR5000, manufactured by Mitsui Chemicals, Inc., hydroxyl equivalent: 180 g / eq) 48.3 g (0.27 g equivalent) and biphenol type epoxy resin as epoxy resin (Product name: YX4000H, manufactured by Japan Epoxy Resin Co., Ltd., epoxy equivalent 193 gZeq) was replaced with 51.7 g (0.27 g equivalent) in the same manner as in Example 1. The results are shown in Table 2.
- Phenolic aralkyl resin (trade name: XLC-4L, manufactured by Mitsui Chemicals, Ltd., hydroxyl equivalent: 172gZeq) 47.lg (0.27g equivalent) as epoxy resin and biphenol type epoxy resin (product) Name: YX4000H, manufactured by Japan Epoxy Resin Co., Ltd., experiment was carried out in the same manner as in Example 1 except that 52.9 g (0.27 g equivalent) of the epoxy equivalent was changed to 52.9 g. Table 2 shows the results.
- NC3000 manufactured by Nippon Kayaku Co., Ltd.
- epoxy equivalent 273 gZeq epoxy equivalent
- Modified phenol biphenylaralkyl resin of Synthesis Example 11 as a curing agent (hydroxyl equivalent 254 g / eq) 48.2 g (0.19 g equivalent), triphenylphosphine lg (1%) as a curing accelerator,
- the experiment was conducted. The results are shown in Table 1.
- Phenolic biphenyl alcohol as a curing agent (trade name: MEH7851SS, manufactured by Meiwa Kasei Co., Ltd., hydroxyl equivalent 230 gZeq) 45.7 g (0.20 g equivalent), triphenylphosphine lg (1%) as a curing accelerator Except that the bifa-aralkyl-type epoxy resin (trade name: NC3000, manufactured by Nippon Shayaku Co., Ltd., epoxy equivalent 273gZeq) was replaced with 54.3g (0.20g equivalent) as epoxy resin The experiment was conducted in the same manner as in Example 1. The results are shown in Table 2.
- the experiment was conducted in the same manner as in Example 1 except that the epoxy equivalent (193 g / eq) was changed to 42. Og (0.22 g equivalent). The results are shown in Table 1.
- Naphthol aralkyl resin as a curing agent (trade name: Hi-NX-3.2, manufactured by Mitsui Chemicals, Ltd., hydroxyl equivalent 218gZeq) 53. Og (0.24g equivalent) and biphenol type epoxy as epoxy resin
- the experiment was conducted in the same manner as in Example 1 except that the resin (trade name: YX4000H, manufactured by Japan Epoxy Resin Co., Ltd., epoxy equivalent 193 gZeq) was replaced with 47. Og (0.24 g equivalent).
- the results are shown in Table 2.
- Oral pentagene resin (Comparative Example 3) is 91 hours, modified phenol dicyclopentagen resin of the present invention is 149 hours (Example 4), and phenol alcohol resin (Comparative Example 4) is 240 hours.
- modified phenolic aralkyl resin of the present invention 374 to 408 hours (Examples 5 to 8)
- the phenolic bialkyl alcohol (Comparative Example 5) is 276 hours
- the modified phenolic bialkyl alcohol of the present invention In 355 to 408 hours (Examples 9 and 10)
- naphthol aralkyl resin (Comparative Example 6) was 206 hours, whereas in the modified naphthol aralkyl resin of the present invention, 374 hours (Example 11).
- the modified phenolic resin of the present invention has an extremely superior effect in durability and moisture resistance compared to the conventional phenolic resin. Further, the flame retardancy is phenol novolak resin (Comparative Example 1) according to UL94 test evaluation criteria. Is V-1 In the modified phenol novolac resin of the invention, V-0 and phenol aralkyl resin (Comparative Example 4) are V-1, whereas in the modified phenol alcohol resin of the present invention, V-0 to Vl, naphthol The aralkyl resin (Comparative Example 6) is V-1 while the modified naphthol aralkyl resin of the present invention is V-0 (Example 11), and the modified phenol resin of the present invention is a conventional phenol resin. Compared to the above, it has excellent flame retardancy.
- the laminates produced in the examples and comparative examples were cut out and measured using a TMA device (Shimadzu TMA-50) in the compression mode under the following conditions. Load 10g, constant speed load mode, measurement conditions 5 ° CZmin, room temperature to 300 ° C, atmosphere nitrogen gas, flow rate 100mlZmin.
- Specimens were treated for 3 hours in a steam bath at 121 ° C and pressure 2.0 atm. After immersion for 20 seconds (C-3Z121Z100), the presence or absence of abnormalities in appearance such as swelling and peeling was examined.
- the hydroxyl group content in phenolic resin was determined by acetylating with pyridine as a solvent, acetic anhydride, and titrating the acetic acid produced after decomposition of the excess reagent with water with a potassium hydroxide solution.
- Synthesis Example 13 the same procedure as in Synthesis Example 1 was carried out except that the amount of 2-thiophene methanol was changed to 57. lg, the reaction time was 6 hours, and the addition amount of dimethyl sulfate was changed to 0.4 g.
- the molecular weight change was measured with gel permeation chromatography, and the disappearance of 2-thiophene methanol was measured with gas chromatography, and there was no 2-thiophene methanol in the system. After confirming that the modified phenolic resin represented by chemical formula (1) It was discharged to the s bat.
- Modified phenol novolac resin obtained in Synthesis Example 13 as a curing agent (hydroxyl equivalent: 155 g / eq) 44.3 g (79.5 parts by weight, hydroxyl equivalent: 1 with respect to epoxy equivalent: 1), ortho-cresol as epoxy resin Novolac-type epoxy resin (trade name: EOCN-102S, Nippon Kayaku Co., Ltd., epoxy equivalent 195 gZeq) 55.7 g (100 parts by weight), TP P (triphenylphosphine) as curing catalyst 2.
- Og was dissolved in 67 g of methyl ethyl ketone to prepare a varnish.
- the gel time of the obtained varnish at 140 ° C was 7 minutes.
- the varnish was impregnated into a glass substrate (Nittobo, 100 m, E glass cloth) and dried at 140 ° C. for 5 minutes to obtain a prepreg.
- the obtained pre-preda was tack-free and excellent in workability.
- 10 sheets of this pre-preda are stacked, 18 / zm thick electrolytic copper foil (Mitsui Metal) is stacked on both sides of the outer layer, laminated at a temperature of 175 ° C and a molding pressure of 2.45 MPa for 2 hours, and a 50% fat content.
- a double-sided copper-clad laminate with a thickness of 1.2 mm was obtained.
- Example 13 Modified phenol novolac resin of Synthesis Example 14 as a curing agent (hydroxyl group equivalent 204 g / eq) 5 1.4 g (105.5 parts by weight, hydroxyl group equivalent 1 to epoxy equivalent 1) and ortho-cresol novolac type epoxy resin (Product name: EOCN-102S, Nippon Kayaku Co., Ltd., epoxy equivalent 195 g / eq) was replaced with 48.6 g (100 parts by weight), and an experiment was conducted in the same manner as in Example 12. The results are shown in Table 3.
- phenol novolac resin (trade name: PSM-4261, manufactured by Gunei Chemical Co., Ltd., hydroxyl equivalent 107gZeq) 35.4g (54.4 parts by weight, hydroxyl equivalent 1 to epoxy equivalent 1)
- epoxy resin Ortho-cresol novolac-type epoxy resin (trade name: EOC N-102S, Nippon Kayaku Co., Ltd., epoxy equivalent 195 gZeq) was replaced with 64.6 g (100 parts by weight) in the same manner as in Example 12. The experiment was conducted. The results are shown in Table 3.
- phenol aralkyl resin (trade name: XLC-4L, manufactured by Mitsui Chemicals, Ltd., hydroxyl equivalent 172 gZeq) 41.7 g (71.5 parts by weight, hydroxyl equivalent 1 with respect to epoxy equivalent 1) and epoxy resin
- 58.3 g (100 parts by weight) of phenol aralkyl epoxy resin (trade name: E-XLC4L, manufactured by Mitsui Chemicals, Inc., epoxy equivalent 240 gZeq) was used. went.
- the results are shown in Table 3.
- the modified phenolic resin of the present invention has a structure in which the side chain of the aromatic ring having a hydroxyl group is substituted with a group represented by the general formula (12), so that the conventional phenolic novolak resin and phenolic
- the thermal properties of the glass transition temperature possessed by the aralkyl resin could be greatly improved without any loss in adhesion and flame retardancy.
- Comparative Example 7 is 14.1 and 15.5 NZcm in Examples 12 and 13 in which the modified phenol novolac resin of the present invention was used against 14. INZcm.
- Comparative Example 8 17.2 NZcm, whereas in Example 14 using the modified phenol aralkyl resin of the present invention, 18.INZcm. Therefore, when the modified phenolic resin of the present invention is used, it has an effect of being extremely excellent in adhesion as compared with the conventional phenolic resin.
- Comparative Example 7 was out of specification, whereas in Examples 12 and 13, V-1 and Comparative Example 8 were V-1, whereas Example 14 is V-0 and has excellent flame retardancy.
- An epoxy resin composition using the modified phenol resin of the present invention as a curing agent an epoxy resin composition using the epoxy resin composition, an insulating material for electrical / electronic parts such as a semiconductor sealing material, and a printed wiring Widely used for laminates such as substrates, adhesives, molding materials, paints, etc.
- the pre-preda of the present invention in which a glass substrate is impregnated with an epoxy resin composition, a laminated board on which the epoxy resin composition is laminated, and an electronic circuit board using the laminated board are home appliances, industrial machines, personal computers, mobile phones, etc. Widely used in printed wiring boards used in various communication equipment, various control devices, automobiles, trains, airplanes, etc.
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Description
Claims
Priority Applications (3)
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US11/793,710 US8053378B2 (en) | 2004-12-21 | 2005-12-16 | Modified phenolic resin, epoxy resin composition containing the same, and prepreg containing the composition |
CN2005800436359A CN101084250B (zh) | 2004-12-21 | 2005-12-16 | 改性酚树脂、含有它的环氧树脂组合物及使用该组合物的预浸料坯 |
JP2006548948A JP4658070B2 (ja) | 2004-12-21 | 2005-12-16 | 変性フェノール樹脂、それを含むエポキシ樹脂組成物およびこれを用いたプリプレグ |
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JP (1) | JP4658070B2 (ja) |
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JP2010107790A (ja) * | 2008-10-31 | 2010-05-13 | Jsr Corp | レジスト下層膜形成用組成物及びパターン形成方法 |
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JP7266881B2 (ja) * | 2018-01-30 | 2023-05-01 | ナミックス株式会社 | 光硬化性および熱硬化性を有する樹脂組成物およびその硬化物、接着剤、半導体装置、ならびに電子部品 |
CN114645376B (zh) * | 2022-05-13 | 2022-08-23 | 浙江星辉新材料科技有限公司 | 一种低密度碳纤维硬质保温毡的制备方法 |
CN117801197B (zh) * | 2024-02-27 | 2024-05-17 | 安徽觅拓材料科技有限公司 | 一种苯酚抗结晶剂的制备方法及应用 |
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- 2005-12-16 CN CN2005800436359A patent/CN101084250B/zh not_active Expired - Fee Related
- 2005-12-16 US US11/793,710 patent/US8053378B2/en not_active Expired - Fee Related
- 2005-12-16 JP JP2006548948A patent/JP4658070B2/ja not_active Expired - Fee Related
- 2005-12-16 WO PCT/JP2005/023183 patent/WO2006068063A1/ja not_active Application Discontinuation
- 2005-12-16 KR KR1020077013819A patent/KR100904055B1/ko active IP Right Grant
- 2005-12-21 TW TW94145519A patent/TWI311571B/zh not_active IP Right Cessation
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Also Published As
Publication number | Publication date |
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CN101084250A (zh) | 2007-12-05 |
KR100904055B1 (ko) | 2009-06-23 |
JPWO2006068063A1 (ja) | 2008-06-12 |
US8053378B2 (en) | 2011-11-08 |
TWI311571B (en) | 2009-07-01 |
KR20070089942A (ko) | 2007-09-04 |
TW200635985A (en) | 2006-10-16 |
US20080044667A1 (en) | 2008-02-21 |
JP4658070B2 (ja) | 2011-03-23 |
CN101084250B (zh) | 2011-06-15 |
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