KR101476895B1 - Resin compositions and metal foil laminate comprising the resin composition - Google Patents
Resin compositions and metal foil laminate comprising the resin composition Download PDFInfo
- Publication number
- KR101476895B1 KR101476895B1 KR1020120153762A KR20120153762A KR101476895B1 KR 101476895 B1 KR101476895 B1 KR 101476895B1 KR 1020120153762 A KR1020120153762 A KR 1020120153762A KR 20120153762 A KR20120153762 A KR 20120153762A KR 101476895 B1 KR101476895 B1 KR 101476895B1
- Authority
- KR
- South Korea
- Prior art keywords
- resin
- integer
- polyphenylene oxide
- type epoxy
- resin composition
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 52
- 239000011888 foil Substances 0.000 title claims abstract description 17
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 17
- 239000002184 metal Substances 0.000 title claims abstract description 17
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 47
- 229920006380 polyphenylene oxide Polymers 0.000 claims abstract description 47
- 229920005989 resin Polymers 0.000 claims abstract description 31
- 239000011347 resin Substances 0.000 claims abstract description 31
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- 239000011256 inorganic filler Substances 0.000 claims abstract description 10
- 229910003475 inorganic filler Inorganic materials 0.000 claims abstract description 10
- 239000003822 epoxy resin Substances 0.000 claims description 37
- 229920000647 polyepoxide Polymers 0.000 claims description 37
- 229920003986 novolac Polymers 0.000 claims description 13
- 125000000732 arylene group Chemical group 0.000 claims description 12
- 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 claims description 11
- 239000000758 substrate Substances 0.000 claims description 10
- 239000000835 fiber Substances 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 7
- 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 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 239000003063 flame retardant Substances 0.000 claims description 6
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 229930003836 cresol Natural products 0.000 claims description 4
- 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 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 claims description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000011889 copper foil Substances 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 2
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- -1 polyphenylene Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920006231 aramid fiber Polymers 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000012757 flame retardant agent Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-VENIDDJXSA-N palladium-100 Chemical compound [100Pd] KDLHZDBZIXYQEI-VENIDDJXSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
- C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
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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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
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- 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
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- 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
- B32B15/14—Layered products comprising a layer of metal next to a fibrous or filamentary layer
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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
- C08G59/20—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 epoxy compounds used
- C08G59/22—Di-epoxy compounds
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/48—Polymers modified by chemical after-treatment
- C08G65/485—Polyphenylene oxides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
- C08L71/123—Polyphenylene oxides not modified by chemical after-treatment
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
- C08L71/126—Polyphenylene oxides modified by chemical after-treatment
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
- B32B2260/02—Composition of the impregnated, bonded or embedded layer
- B32B2260/021—Fibrous or filamentary layer
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
- B32B2260/04—Impregnation, embedding, or binder material
- B32B2260/046—Synthetic resin
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
- B32B2307/20—Properties of the layers or laminate having particular electrical or magnetic properties, e.g. piezoelectric
- B32B2307/204—Di-electric
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- 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
- B32B2307/00—Properties of the layers or laminate
- B32B2307/30—Properties of the layers or laminate having particular thermal properties
- B32B2307/306—Resistant to heat
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- 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
- B32B2457/00—Electrical equipment
- B32B2457/08—PCBs, i.e. printed circuit boards
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2371/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
- C08J2371/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08J2371/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08J2371/12—Polyphenylene oxides
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Abstract
본 발명은 수지 조성물 및 상기 수지 조성물를 이용하여 제조된 프리프레그를 포함하는 금속박 적층체에 것으로, 상기 수지 조성물은 에폭시화 폴리페닐렌 옥사이드 수지; 무기 필러; 경화제; 및 경화촉진제를 포함한다.The present invention relates to a metal foil laminate comprising a resin composition and a prepreg produced using the resin composition, wherein the resin composition comprises an epoxidized polyphenylene oxide resin; Inorganic filler; Curing agent; And a curing accelerator.
Description
본 발명은 금속박 적층체의 졀연층에 사용되는 수지 조성물 및 상기 수지 조성물을 포함하는 금속박 적층체에 관한 것이다.The present invention relates to a resin composition for use in a laminate of a metal foil laminate and a metal foil laminate including the resin composition.
최근 전자기기의 고성능화가 요구됨에 따라 고주파(GHz) 영역에서 유전손실이 적고 전송특성이 우수한 인쇄 회로 기판이 요구되고 있다. 인쇄 회로 기판은 프리프레그에 동박이 적층된 동박 적층체를 이용하여 제조되며, 상기 동박 적층체 제조시 사용되는 프리프레그는 주로 에폭시 수지를 함유하고 있다.BACKGROUND ART [0002] With the recent demand for high performance of electronic devices, a printed circuit board having a low dielectric loss and excellent transmission characteristics in a high frequency (GHz) region is required. A printed circuit board is manufactured using a copper foil laminate in which a copper foil is laminated on a prepreg, and a prepreg used in the production of the copper foil laminate mainly contains an epoxy resin.
그런데, 에폭시 수지는 접착성 및 내열성이 우수하지만 고주파 영역에서 신호의 전파속도 및 임피던스 제어에 불리하게 작용하여 인쇄 회로 기판의 유전율 및 유전손실을 낮추는데 한계가 있었다.However, the epoxy resin has excellent adhesion and heat resistance, but has a limitation in lowering the permittivity and dielectric loss of the printed circuit board because it adversely affects signal propagation speed and impedance control in a high frequency range.
따라서, 인쇄 회로 기판의 유전율 및 유전손실을 낮추기 위해 저유전 특성을 가지는 폴리페닐렌 옥사이드를 에폭시 수지와 혼합하여 프리프레그를 제조한 후 이를 이용하여 인쇄 회로 기판을 제조하는 기술이 제안되었다. 그러나, 폴리페닐렌 옥사이드는 열가소성 수지이기 때문에 접착성 및 내열성이 떨어지고, 에폭시 수지와 반응할 수 있는 알코올기가 1개이기 때문에 에폭시 수지와의 경화성도 떨어지는 문제점이 있었다.Accordingly, a technique has been proposed in which prepregs are prepared by mixing polyphenylene oxide having low dielectric properties with an epoxy resin in order to lower the dielectric constant and dielectric loss of a printed circuit board, and then, a printed circuit board is manufactured using the prepared prepregs. However, since polyphenylene oxide is a thermoplastic resin, adhesiveness and heat resistance are inferior, and there is only one alcohol group capable of reacting with the epoxy resin, so that there is a problem that the curing property with the epoxy resin is deteriorated.
이러한 문제점을 개선하기 위해 폴리페닐렌 옥사이드를 재분배 또는 변성하여 양말단에 알코올기가 도입된 폴리페닐렌 옥사이드나 양말단에 비닐기가 도입된 폴리페닐렌 옥사이드를 사용하는 기술이 제안되었지만, 여전히 인쇄 회로 기판에서 요구되는 접착성, 내열성 및 경화성을 얻기에 한계가 있었다.In order to solve such a problem, there has been proposed a technique of redistributing or modifying polyphenylene oxide to use polyphenylene oxide having an alcohol group introduced at both ends thereof or polyphenylene oxide having a vinyl group introduced at both ends thereof. However, Heat resistance and curability required by the present invention.
본 발명은 상기한 문제점을 해결하기 위해, 저유전 특성을 가지면서도 접착성, 내열성 및 경화성이 우수한 수지 조성물 및 상기 수지 조성물을 포함하는 프리프레그를 제공하는 것을 목적으로 한다.In order to solve the above-described problems, it is an object of the present invention to provide a resin composition excellent in adhesiveness, heat resistance and curability while having low dielectric properties, and a prepreg comprising the resin composition.
또한, 본 발명은 상기 프리프레그를 포함하는 금속박 적층체 및 상기 금속박 적층체를 이용하여 제조된 인쇄 회로 기판을 제공하는 것도 목적으로 한다.It is also an object of the present invention to provide a metal foil laminate including the prepreg and a printed circuit board manufactured using the metal foil laminate.
상기한 목적을 달성하기 위해 본 발명은, 에폭시화 폴리페닐렌 옥사이드 수지; 무기 필러; 경화제; 및 경화촉진제를 포함하는 수지 조성물을 제공한다.In order to achieve the above object, the present invention provides an epoxy resin composition comprising: an epoxidized polyphenylene oxide resin; Inorganic filler; Curing agent; And a curing accelerator.
여기서, 상기 에폭시화 폴리페닐렌 옥사이드 수지는 하기 화학식 1로 표시되는 에폭시 말단 폴리페닐렌 옥사이드 수지 또는 하기 화학식 2로 표시되는 디시클로펜타디엔 에폭시 말단 폴리페닐렌 옥사이드 수지일 수 있다.Here, the epoxidized polyphenylene oxide resin may be an epoxy-terminated polyphenylene oxide resin represented by the following formula (1) or a dicyclopentadiene epoxy-terminated polyphenylene oxide resin represented by the following formula (2).
[화학식 1][Chemical Formula 1]
상기 화학식 1에서, X는 치환 또는 비치환된 C6~C40의 아릴렌기이며, n는 1 내지 10의 정수이고, m은 1 내지 10의 정수이다.X is a substituted or unsubstituted C 6 -C 40 arylene group, n is an integer of 1 to 10, and m is an integer of 1 to 10.
[화학식 2](2)
상기 화학식 2에서, X는 치환 또는 비치환된 C6~C40의 아릴렌기이며, n는 1 내지 10의 정수이고, m은 1 내지 10의 정수이며, p는 1 내지 5의 정수이고, q는 1 내지 5의 정수이다.X is a substituted or unsubstituted C 6 -C 40 arylene group, n is an integer of 1 to 10, m is an integer of 1 to 10, p is an integer of 1 to 5, q Is an integer of 1 to 5.
또한, 상기 경화제는 하기 화학식 3으로 표시되는 알코올 말단 폴리페닐렌 옥사이드 수지 또는 하기 화학식 4로 표시되는 아민 말단 폴리페닐렌 옥사이드 수지일 수 있다.The curing agent may be an alcohol-terminated polyphenylene oxide resin represented by the following formula (3) or an amine-terminated polyphenylene oxide resin represented by the following formula (4).
[화학식 3](3)
상기 화학식 3에서, X는 치환 또는 비치환된 C6~C40의 아릴렌기이며, n는 1 내지 10의 정수이고, m은 1 내지 10의 정수이다.X is a substituted or unsubstituted C 6 -C 40 arylene group, n is an integer of 1 to 10, and m is an integer of 1 to 10.
[화학식 4][Chemical Formula 4]
상기 화학식 4에서, X는 치환 또는 비치환된 C6~C40의 아릴렌기이며, n는 1 내지 10의 정수이고, m은 1 내지 10의 정수이다.X is a substituted or unsubstituted C 6 -C 40 arylene group, n is an integer of 1 to 10, and m is an integer of 1 to 10.
한편, 본 발명은 섬유 기재; 및 상기 섬유 기재에 함침되는 상기 수지 조성물 을 포함하는 프리프레그를 제공한다.On the other hand, the present invention relates to a fibrous substrate; And a prepreg containing the resin composition impregnated in the fiber substrate.
또, 본 발명은 상기 프리프레그를 포함하는 금속박 적층체와 상기 금속박 적층체를 이용하여 제조된 인쇄 회로 기판도 제공한다.The present invention also provides a metal foil laminate including the prepreg and a printed circuit board manufactured using the metal foil laminate.
본 발명에 따른 수지 조성물은 에폭시화 폴리페닐렌 옥사이드 수지와 아민 말단 폴리페닐렌 옥사이드 수지를 포함하기 때문에 저유전성을 나타내면서도 접착성 및 내열성이 우수하고 경화성 또한 뛰어나다. 따라서, 이러한 본 발명의 수지 조성물을 이용하여 인쇄 회로 기판을 제조할 경우 유전율 및 유전손실이 낮으며, 접착성 및 내열성이 우수한 인쇄 회로 기판을 제공할 수 있다.The resin composition according to the present invention exhibits excellent adhesiveness and heat resistance, and is also excellent in curability because it contains an epoxidized polyphenylene oxide resin and an amine-terminated polyphenylene oxide resin. Accordingly, when a printed circuit board is manufactured using the resin composition of the present invention, it is possible to provide a printed circuit board having a low dielectric constant and dielectric loss, and excellent adhesion and heat resistance.
이하, 본 발명을 설명한다.
Hereinafter, the present invention will be described.
1. 수지 조성물1. Resin composition
본 발명의 수지 조성물은 에폭시화 폴리페닐렌 옥사이드 수지, 무기 필러, 경화제 및 경화촉진제를 포함한다.The resin composition of the present invention includes an epoxidized polyphenylene oxide resin, an inorganic filler, a curing agent and a curing accelerator.
본 발명의 수지 조성물에 포함되는 에폭시화 폴리페닐렌 옥사이드 수지는 저유전 특성을 나타내는 폴리페닐렌 옥사이드와 우수한 접착성 및 열경화성을 나타내는 에폭시기(epoxy group)가 결합되어 있어 수지 조성물의 유전율을 낮추고 접착성을 높이는 역할을 수행한다. 이러한 에폭시화 폴리페닐렌 옥사이드 수지는 알코올 말단 폴리페닐렌 옥사이드를 에폭시화한 것으로, 하기 화학식 1로 표시되는 에폭시 말단 폴리페닐렌 옥사이드 수지이거나 하기 화학식 2로 표시되는 디시클로펜타디엔 에폭시 말단 폴리페닐렌 옥사이드 수지인 것이 바람직하다.The epoxidized polyphenylene oxide resin included in the resin composition of the present invention is a polyphenylene oxide having low dielectric properties and an epoxy group showing excellent adhesiveness and thermosetting property, . Such an epoxidized polyphenylene oxide resin is an epoxidized alcohol-terminated polyphenylene oxide, and may be an epoxy-terminated polyphenylene oxide resin represented by the following formula (1) or a dicyclopentadiene epoxy-terminated polyphenylene It is preferable that the resin is an oxide resin.
[화학식 1][Chemical Formula 1]
상기 화학식 1에서, X는 치환 또는 비치환된 C6~C40의 아릴렌기이며, n는 1 내지 10의 정수이고, m은 1 내지 10의 정수이다.X is a substituted or unsubstituted C 6 -C 40 arylene group, n is an integer of 1 to 10, and m is an integer of 1 to 10.
[화학식 2](2)
상기 화학식 2에서, X는 치환 또는 비치환된 C6~C40의 아릴렌기이며, n는 1 내지 10의 정수이고, m은 1 내지 10의 정수이며, p는 1 내지 5의 정수이고, q는 1 내지 5의 정수이다.X is a substituted or unsubstituted C 6 -C 40 arylene group, n is an integer of 1 to 10, m is an integer of 1 to 10, p is an integer of 1 to 5, q Is an integer of 1 to 5.
이때, 상기 화학식 1 및 2의 X는 구체적으로 2개 이상의 수산기(수산기(OH)는
이러한 본 발명의 수지 조성물에 포함되는 에폭시화 폴리페닐렌 옥사이드 수지의 함량은 특별히 한정되지 않으나, 수지 조성물의 유전성, 접착성, 내열성 및 경화성 등을 고려할 때, 수지 조성물 100중량%를 기준으로 5 내지 60중량%로 포함되는 것이 바람직하고, 10 내지 50중량%로 포함되는 것이 더욱 바람직하다.The content of the epoxidized polyphenylene oxide resin contained in the resin composition of the present invention is not particularly limited. However, considering the dielectric property, adhesive property, heat resistance and curability of the resin composition, By weight, more preferably from 10 to 50% by weight.
본 발명의 수지 조성물에 포함되는 무기 필러는 수지 조성물의 점도를 조절하고(성형성 향상), 경화된 수지 조성물의 열전도율을 높이는 역할을 수행한다.The inorganic filler contained in the resin composition of the present invention controls the viscosity of the resin composition (improves moldability) and enhances the thermal conductivity of the cured resin composition.
이러한 무기 필러는 당업계에 공지된 것이라면 특별히 한정되지 않으나, 산화규소, 산화알루미늄, 산화아연, 질화알루미늄, 질화규소, 질화붕소, 실리카, 탈크, 탄산칼슘 및 탄산마그네슘으로 이루어진 군에서 선택된 1종 이상을 사용하는 것이 바람직하다.Such an inorganic filler is not particularly limited as long as it is well known in the art, and it may be at least one selected from the group consisting of silicon oxide, aluminum oxide, zinc oxide, aluminum nitride, silicon nitride, boron nitride, silica, talc, calcium carbonate, Is preferably used.
여기서, 본 발명의 수지 조성물에 포함되는 무기 필러의 함량은 특별히 한정되지 않으나, 수지 조성물의 점도, 열전도성, 작업성 및 성형성 등을 고려할 때, 수지 조성물 100중량%를 기준으로 10 내지 50중량%로 포함되는 것이 바람직하고, 30 내지 40중량%로 포함되는 것이 더욱 바람직하다.The content of the inorganic filler contained in the resin composition of the present invention is not particularly limited. However, considering the viscosity, thermal conductivity, workability and moldability of the resin composition, the content of the inorganic filler is preferably 10 to 50 wt% %, More preferably from 30 to 40 wt%.
본 발명의 수지 조성물에 포함되는 경화제는 상기 에폭시화 폴리페닐렌 옥사이드 수지와 후술되는 에폭시 수지의 경화반응을 일으키는 역할을 수행한다. 이러한 경화제는 당업계에 공지된 것이라면 특별히 한정되지 않으나, 하기 화학식 3으로 표시되는 알코올 말단 폴리페닐렌 옥사이드 수지 또는 하기 화학식 4로 표시되는 아민 말단 폴리페닐렌 옥사이드 수지를 사용하는 것이 바람직하며, 화학식 4로 표시되는 아민 말단 폴리페닐렌 옥사이드 수지를 사용하는 것이 더욱 바람직하다. 화학식 4로 표시되는 아민 말단 폴리페닐렌 옥사이드 수지를 사용할 경우 아민 말단기와 에폭시기의 가교결합에 의해 수지 조성물의 가교밀도를 높일 수 있기 때문이다. 여기서, 수지 조성물의 가교밀도가 높아질 경우 경화된 수지 조성물의 유리전이온도를 높이는 효과가 있다.The curing agent contained in the resin composition of the present invention plays a role of causing a curing reaction between the epoxidized polyphenylene oxide resin and an epoxy resin described later. The curing agent is not particularly limited as long as it is known in the art, but it is preferable to use an alcohol-terminated polyphenylene oxide resin represented by the following formula (3) or an amine-terminated polyphenylene oxide resin represented by the following formula It is more preferable to use an amine-terminated polyphenylene oxide resin. When the amine-terminated polyphenylene oxide resin represented by the general formula (4) is used, the crosslinking density of the resin composition can be increased by cross-linking the amine terminal group and the epoxy group. Here, when the crosslinking density of the resin composition is high, the glass transition temperature of the cured resin composition is increased.
[화학식 3](3)
상기 화학식 3에서, X는 치환 또는 비치환된 C6~C40의 아릴렌기이며, n는 1 내지 10의 정수이고, m은 1 내지 10의 정수이다.X is a substituted or unsubstituted C 6 -C 40 arylene group, n is an integer of 1 to 10, and m is an integer of 1 to 10.
[화학식 4][Chemical Formula 4]
상기 화학식 4에서, X는 치환 또는 비치환된 C6~C40의 아릴렌기이며, n는 1 내지 10의 정수이고, m은 1 내지 10의 정수이다.X is a substituted or unsubstituted C 6 -C 40 arylene group, n is an integer of 1 to 10, and m is an integer of 1 to 10.
이때, 상기 화학식 3 및 4의 X는 구체적으로 2개 이상의 수산기(수산기(OH)는
이러한 본 발명의 수지 조성물에 포함되는 경화제의 함량은 특별히 한정되지 않으나, 수지 조성물의 경화성(가교밀도), 작업성 및 성형성 등을 고려할 때, 수지 조성물 100중량%를 기준으로 5 내지 40중량% 로 포함되는 것이 바람직하고, 20 내지 30중량%로 포함되는 것이 더욱 바람직하다.The content of the curing agent contained in the resin composition of the present invention is not particularly limited. However, considering the curing property (crosslinking density), workability and moldability of the resin composition, the content of the curing agent is preferably 5 to 40 wt% , More preferably from 20 to 30% by weight.
본 발명의 수지 조성물에 포함되는 경화촉진제는 경화반응 속도를 높이는 역할을 수행한다. 이러한 경화촉진제는 당업계에 공지된 것이라면 특별히 한정되지 않으나, 3급 아민 계열, 이미다졸 계열 또는 유기 포스핀 계열을 사용하는 것이 바람직하다.The curing accelerator included in the resin composition of the present invention plays a role of increasing the curing reaction rate. The curing accelerator is not particularly limited as long as it is known in the art, but it is preferable to use a tertiary amine series, imidazole series or organophosphine series.
또한, 본 발명의 수지 조성물에 포함되는 경화촉진제의 함량도 특별히 한정되지 않으나, 수지 조성물의 경화 반응성, 작업성 및 성형성 등을 고려할 때, 수지 조성물 100중량%를 기준으로 0.01 내지 5 중량%로 포함되는 것이 바람직하고, 0.1 내지 3중량%로 포함되는 것이 더욱 바람직하다.The content of the curing accelerator contained in the resin composition of the present invention is not particularly limited. However, considering the curing reactivity, workability and moldability of the resin composition, 0.01 to 5% by weight , More preferably from 0.1 to 3% by weight.
한편, 본 발명의 수지 조성물은 수지 조성물의 내열성 및 접착성 확보를 위해 가교밀도를 조절할 수 있는 에폭시 수지를 더 포함할 수 있다. 이때, 사용 가능한 에폭시 수지는 당업계에 공지된 것이라면 특별히 한정되지 않으나, 비스페놀 A형 에폭시 수지, 수소 첨가 비스페놀 A형 에폭시 수지, 비스페놀 F형 에폭시 수지, 비스페놀 S형 에폭시 수지, 노볼락형 에폭시 수지, 크레졸 노볼락형 에폭시 수지, 페놀 노볼락형 에폭시 수지, 디시클로펜타디엔형 에폭시 수지, 트리페닐메탄형 에폭시 수지, 나프탈렌형 에폭시 수지, 비페닐형 에폭시 수지 및 수소 첨가 비페닐형 에폭시 수지로 이루어진 군에서 선택된 1종 이상을 사용하는 것이 바람직하다.Meanwhile, the resin composition of the present invention may further comprise an epoxy resin capable of controlling the crosslinking density for securing the heat resistance and adhesion of the resin composition. The epoxy resin which can be used is not particularly limited as long as it is known in the art, and examples thereof include bisphenol A type epoxy resin, hydrogenated bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, novolak type epoxy resin, Cresol novolak type epoxy resin, phenol novolak type epoxy resin, dicyclopentadiene type epoxy resin, triphenylmethane type epoxy resin, naphthalene type epoxy resin, biphenyl type epoxy resin and hydrogenated biphenyl type epoxy resin It is preferable to use at least one selected from the above.
또한, 본 발명의 수지 조성물에 더 포함되는 에폭시 수지의 함량도 특별히 한정되지 않으나, 수지 조성물의 가교 성형성, 내열성 및 접착성 등을 고려할 때, 수지 조성물 100중량%를 기준으로 20 내지 80중량%로 포함되는 것이 바람직하고, 20 내지 40중량%로 포함되는 것이 더욱 바람직하다.The content of the epoxy resin further included in the resin composition of the present invention is not particularly limited. However, considering the crosslinking moldability, heat resistance and adhesiveness of the resin composition, the content of the epoxy resin is preferably 20 to 80 wt% , More preferably from 20 to 40% by weight.
본 발명의 수지 조성물은 난연성을 높이기 위해 난연제를 더 포함할 수 있다. 이때, 사용 가능한 난연제는 당업계에 공지된 것이라면 특별히 한정되지 않으나, 인계 난연제인 것이 바람직하다. 이러한 인계 난연제의 비제한적인 예로는 Phosphazene계, Phosphate계, Phosphine oxide계, Phosphite계, Phosphonate계 등을 들 수 있다.The resin composition of the present invention may further include a flame retardant agent to enhance flame retardancy. At this time, the flame retardant which can be used is not particularly limited as far as it is known in the art, but it is preferably a phosphorus flame retardant. Non-limiting examples of the phosphorus flame retardant include a phosphazene system, a phosphate system, a phosphine oxide system, a phosphite system, and a phosphonate system.
또한, 본 발명의 수지 조성물에 더 포함되는 난연제의 함량도 특별히 한정되지 않으나, 수지 조성물의 물성을 고려할 때, 수지 조성물 100중량%를 기준으로 1 내지 50중량%로 포함되는 것이 바람직하고, 20 내지 40중량%로 포함되는 것이 더욱 바람직하다.Also, the content of the flame retardant further contained in the resin composition of the present invention is not particularly limited. However, considering the physical properties of the resin composition, it is preferably contained in an amount of 1 to 50% by weight based on 100% by weight of the resin composition, More preferably 40% by weight.
한편, 본 발명의 수지 조성물은 그 물성 및 발휘되는 효과를 벗어나지 않는 범위 내에서 당업계에 공지된 첨가제(예를 들어, 소포제, 분산제, 점도조절제, 산화방지제 등)를 더 포함할 수 있다.
Meanwhile, the resin composition of the present invention may further contain additives (for example, antifoaming agents, dispersants, viscosity adjusting agents, antioxidants, etc.) known in the art within the range not detracting from the physical properties and effects exerted thereon.
2. 2. 프리프레그Prepreg
본 발명은 섬유 기재와 상기 섬유 기재에 함침된 수지 조성물을 포함하는 프리프레그를 제공한다. 여기서, 섬유 기재에 함침되는 수지 조성물에 대한 설명은 상기에서 설명한 바와 동일하므로 생략하기로 한다.The present invention provides a prepreg comprising a fiber substrate and a resin composition impregnated in the fiber substrate. Here, the description of the resin composition impregnated into the fiber substrate is the same as that described above, and thus will not be described.
본 발명의 프리프레그에 포함되는 섬유 기재는 당업계에 공지된 것이라면 특별히 한정되지 않으며, 비제한적인 예로 유리 섬유, 유리 페이퍼, 아라미드(aramid) 섬유, 아라미드 페이퍼 및 탄소 섬유 등을 들 수 있다.The fiber substrate included in the prepreg of the present invention is not particularly limited as long as it is known in the art, and examples thereof include glass fiber, glass paper, aramid fiber, aramid paper and carbon fiber.
이러한 섬유 기재에 함침되는 수지 조성물의 함침량은 특별히 한정되지 않으나, 제조되는 프리프레그의 물성 및 두께를 고려할 때, 프리프레그 100중량%를 기준으로, 30 내지 80중량%로 함침시킬 수 있다(수지 조성물 30 내지 80중량%+섬유 기재 20 내지 70중량%).The impregnated amount of the resin composition impregnated in such a fiber substrate is not particularly limited, but it may be impregnated in an amount of 30 to 80% by weight based on 100% by weight of the prepreg in consideration of physical properties and thickness of the prepared prepreg 30 to 80% by weight of the composition + 20 to 70% by weight of the fiber substrate).
이와 같은 본 발명의 프리프레그는 다양한 분야에 사용될 수 있다. 특히, 본 발명의 프리프레그는 상기에서 설명한 수지 조성물을 포함하기 때문에 저유전성, 내열성 및 접착성 등이 요구되는 인쇄 회로 기판의 재료로 사용할 경우 우수한 효과를 볼 수 있다.
Such a prepreg of the present invention can be used in various fields. In particular, since the prepreg of the present invention includes the resin composition described above, excellent effects can be obtained when it is used as a material for a printed circuit board that requires low dielectric constant, heat resistance, adhesiveness, and the like.
3. 3. 금속박Metal foil 적층체The laminate 및 이를 포함하는 인쇄 회로 기판 And a printed circuit board
본 발명은 프리프레그를 포함하는 금속박 적층체 및 이를 포함하는 인쇄 회로 기판을 제공한다.The present invention provides a metal foil laminate including a prepreg and a printed circuit board comprising the same.
본 발명의 금속박 적층체는 상기에서 설명한 프리프레그를 포함하는 것이라면 그 구조가 특별히 한정되지 않으며, 비제한적인 예로 프리프레그의 양면(상면 및 하면)에 각각 금속박이 적층되어 있는 구조일 수 있다. 여기서, 프리프레그의 양면에 적층되는 금속박으로 사용 가능한 물질은 전도성을 가진 것이라면 특별히 한정되지 않으며, 비제한적인 예로 구리(Cu), 주석(Sn), 금(Au), 은(Ag) 또는 이들의 혼합물을 들 수 있다. 또한, 프리프레그는 하나가 사용되거나 여러 개가 적층된 것을 사용할 수 있다.The structure of the metal foil laminate of the present invention is not particularly limited as long as it includes the above-described prepregs. As a non-limiting example, the metal foil laminate may have a structure in which metal foils are laminated on both surfaces (upper and lower surfaces) of the prepreg. The material usable as the metal foil to be laminated on both sides of the prepreg is not particularly limited as long as it has conductivity, and examples thereof include copper (Cu), tin (Sn), gold (Au), silver (Ag) And mixtures thereof. Also, one prepreg may be used or multiple prepregs may be used.
한편, 본 발명의 인쇄 회로 기판은 상기 금속박 적층체에 회로 패턴을 형성시켜 제조된 것으로, 회로 패턴을 형성시키는 방법은 당업계에 공지된 것이라면 특별히 한정되지 않는다.
On the other hand, the printed circuit board of the present invention is manufactured by forming a circuit pattern on the metal foil laminate, and the method of forming the circuit pattern is not particularly limited as long as it is well known in the art.
이하, 실시예를 들어 본 발명을 보다 상세히 설명한다. 다만, 하기의 실시예는 본 발명의 바람직한 실시예일뿐, 본 발명이 하기 실시예로 한정되는 것은 아니다.
Hereinafter, the present invention will be described in more detail with reference to Examples. However, the following examples are only the preferred embodiments of the present invention, and the present invention is not limited to the following examples.
[[ 합성예Synthetic example 1] 에폭시 말단 폴리페닐렌 1] Epoxy-terminated polyphenylene 옥사이드Oxide 수지 합성 Resin synthesis
온도계, 교반기 및 냉각기를 구비한 5L 둥근바닥 플라스크에 1㎏의 알코올 말단 폴리페닐렌 옥사이드(SABIC社, SA-90, Mw 1,700)와 2.5㎏의 에피클로로하이드린 (40 배 몰%, 대정화금社)을 투입한 후 가열하며 용해시켰다. 이후, 50g의 수산화나트륨 (2.1 배 몰%, 삼전화학社)을 천천히 분할투입하고 100℃에서 12시간 동안 교반시킨 후 상온으로 냉각하였다. 반응물을 메탄올에 침전시켜 2.6㎏의 에폭시화 폴리페닐렌 옥사이드(Mw 1,700)를 수득하였다.
1 kg of an alcohol-terminated polyphenylene oxide (SABIC, SA-90, Mw 1,700) and 2.5 kg of epichlorohydrin (40 times molar%, purified water Ltd.) was added and dissolved by heating. Thereafter, 50 g of sodium hydroxide (2.1-fold molar percent, manufactured by Sanken Chemical Co., Ltd.) was slowly added thereto, stirred at 100 캜 for 12 hours, and cooled to room temperature. The reaction product was precipitated in methanol to obtain 2.6 kg of epoxidized polyphenylene oxide (Mw 1,700).
[[ 합성예Synthetic example 2] 2] 디시클로펜타디엔Dicyclopentadiene (( DCPDDCPD ) 에폭시 말단 폴리페닐렌 ) Epoxy-terminated polyphenylene 옥사이드Oxide 수지 합성 Resin synthesis
온도계, 교반기 및 냉각기를 구비한 5L 둥근바닥 플라스크에 500g의 알코올 말단 폴리페닐렌 옥사이드(SABIC社, SA-90, Mw 1,700)을 1L의 폴리프로필렌 글리콜 모노메틸에테르 아세테이트와 500g의 디시클로펜타디엔(DCPD) 노볼락 에폭시 수지(에피클론 社, HP-7200)와 함께 투입한 후 가열하며 용해시켰다. 이후, 촉매로 2-에틸-4-메틸이미다졸 1g을 투입하고 130℃에서 4시간 동안 교반하였다. 반응물을 메탄올에 침전시켜 1㎏의 DCPD 에폭시화 폴리페닐렌 옥사이드(GPC 중량 평균 분자량(Mw): 4,000~6,000)를 수득하였다.
500 g of an alcohol-terminated polyphenylene oxide (SABIC, SA-90, Mw 1,700) was mixed with 1 L of polypropylene glycol monomethyl ether acetate and 500 g of dicyclopentadiene (manufactured by Wako Pure Chemical Industries, Ltd.) in a 5 L round bottom flask equipped with a stirrer, DCPD) novolak epoxy resin (Epiclon, HP-7200), and then dissolved by heating. Thereafter, 1 g of 2-ethyl-4-methylimidazole was added as a catalyst, and the mixture was stirred at 130 캜 for 4 hours. The reaction product was precipitated in methanol to obtain 1 kg of DCPD epoxidized polyphenylene oxide (GPC weight average molecular weight (Mw): 4,000 to 6,000).
[[ 합성예Synthetic example 3] 아민 말단 폴리페닐렌 3] amine-terminated polyphenylene 옥사이드Oxide 수지 합성 Resin synthesis
온도계, 교반기 및 냉각기를 구비한 5L 둥근바닥 플라스크에 1㎏의 알코올 말단 폴리페닐렌 옥사이드(SABIC社, SA-90, Mw 1,700)을 2L의 디메틸포름아마이드 용액과 함께 투입한 후 80℃로 승온시켜 30분간 교반하였다. 이후, 150g의 1,3-디나이트로벤젠과 300g의 탄산칼륨을 투입하고 150℃에서 8시간 동안 교반하였다. 반응물을 메탄올에 침전시켜 감압 필터로 여과한 후 얻은 침전물을 3L의 2-메톡시에탄올과 함께 5L 둥근바닥 플라스크에 투입하였다. 이후, 수소 분위기하에서 30g의 팔라듐 차콜과 100g의 트리에틸아민을 첨가하고 20시간 동안 반응시켰다. 필터를 통해 촉매를 분리하고 메탄올에 침전시켜 1.1㎏의 아민 말단 폴리페닐렌 옥사이드(Mw 1800)를 수득하였다.
1 kg of an alcohol-terminated polyphenylene oxide (SABIC, SA-90, Mw 1,700) was added to a 5 L round bottom flask equipped with a thermometer, a stirrer and a condenser together with 2 L of dimethylformamide solution, And stirred for 30 minutes. Thereafter, 150 g of 1,3-dinitrobenzene and 300 g of potassium carbonate were added, and the mixture was stirred at 150 DEG C for 8 hours. The reaction product was precipitated in methanol, filtered through a vacuum filter, and the resulting precipitate was added to a 5 L round bottom flask together with 3 L of 2-methoxyethanol. Thereafter, 30 g of palladium charcoal and 100 g of triethylamine were added under a hydrogen atmosphere and reacted for 20 hours. The catalyst was isolated via a filter and precipitated in methanol to give 1.1 kg amine-terminated polyphenylene oxide (Mw 1800).
[[ 실시예Example 1 내지 4] 1 to 4]
하기 표 1과 같은 조성의 수지 조성물을 유리 섬유(Nittobo 社, #2116 E glass)에 함침시킨 후 150℃에서 5분간 건조시켜 전제중량을 기준으로 수지 조성물이 50중량%로 함유되는 프리프레그(두께: 약 0.125mm)를 제조하였다. 제조된 프리프레그를 8장 적층한 후 바깥쪽의 양면에 각각 18㎛ 두께의 동박을 적층하고 180℃, 2MPa의 조건으로 120분간 프레스하여 동박 적층체을 제조하였다.
The resin composition having the composition shown in Table 1 below was impregnated with glass fiber (Nittobo, # 2116 E glass) and dried at 150 ° C for 5 minutes to prepare a prepreg containing 50% by weight of the resin composition based on the total weight : About 0.125 mm). After the eight prepregs were laminated, a copper foil having a thickness of 18 탆 was laminated on both sides of the outside, and pressed at 120 캜 for 120 minutes under the conditions of 180 캜 and 2 MPa to prepare a copper foil laminate.
[[ 비교예Comparative Example 1 및 2] 1 and 2]
하기 표 1과 같은 조성의 수지 조성물을 적용한 것을 제외하고는 상기 실시예 1과 동일한 과정을 거쳐 동박 적층체을 제조하였다.
A copper-clad laminate was prepared in the same manner as in Example 1, except that the resin composition having the composition shown in Table 1 below was used.
옥사이드Epoxidized polyphenylene
Oxide
수지Epoxy
Suzy
(오츠카 케미컬社, SPB-100)Phosphorus flame retardant
(Otsuka Chemical Co., SPB-100)
[[ 실험예Experimental Example ]]
실시예 1 내지 4 및 비교예 1, 2에서 제조된 동박 적층체의 물성을 하기와 같은 방법으로 평가하였으며, 그 결과를 하기 표 2에 나타내었다.Physical properties of the copper-clad laminates prepared in Examples 1 to 4 and Comparative Examples 1 and 2 were evaluated by the following methods, and the results are shown in Table 2 below.
1. 유전율: IPC TM-650.2.5.5.1의 시험 규격에 준하여 물질 분석기(Material Analyzer)를 이용하여 측정하였다.1. Permittivity: The dielectric constant was measured using a material analyzer according to the test standard of IPC TM-650.2.5.5.1.
2. 유전손실: IPC TM-650.2.5.5.1의 시험 규격에 준하여 물질 분석기 (Material Analyzer)를 이용하여 측정하였다.2. Dielectric loss: Measured according to the test standard of IPC TM-650.2.5.5.1 using a material analyzer.
3. 접착성(P/S): IPC-TM-650.2.4.8의 시험 규격에 준하여 측정하였다.3. Adhesion (P / S): Measured according to the test standard of IPC-TM-650.2.4.8.
4. 내열성: 288℃의 납조에서 5cm
5. 유리전이온도(Tg): 동박 적층체의 동박층을 에칭한 후에 DSC (Differential Scanning Calorimeter)를 이용하여 측정하였다.
5. Glass Transition Temperature (Tg): The copper foil layer of the copper-clad laminate was etched and then measured using DSC (Differential Scanning Calorimeter).
(Dk @ 1GHzpermittivity
(Dk @ 1 GHz
(Df @ 1GHz)Dielectric loss
(Df @ 1 GHz)
(S/F @288)Heat resistance
(S / F @ 288)
상기 표 2를 참조하면, 본 발명의 수지 조성물을 이용하여 제조된 동박 적층체(실시예 1 내지 4)는 종래의 수지 조성물을 이용하여 제조된 동박 적층판(비교예 1 및 2)과 동등 수준의 접착성 및 내열성을 나타내면서도 유전율 및 유전손실이 낮은 것을 확인할 수 있다.Referring to Table 2, the copper-clad laminates (Examples 1 to 4) produced using the resin composition of the present invention had the same level of the copper-clad laminates (Comparative Examples 1 and 2) It can be confirmed that the dielectric constant and dielectric loss are low while exhibiting adhesiveness and heat resistance.
Claims (9)
무기 필러;
경화제; 및
경화촉진제를 포함하고,
상기 에폭시화 폴리페닐렌 옥사이드 수지는 하기 화학식 1로 표시되는 에폭시 말단 폴리페닐렌 옥사이드 수지 또는 하기 화학식 2로 표시되는 디시클로펜타디엔 에폭시 말단 폴리페닐렌 옥사이드 수지인 것을 특징으로 하는 수지 조성물.
[화학식 1]
상기 화학식 1에서, X는 치환 또는 비치환된 C6~C40의 아릴렌기이며, n는 1 내지 10의 정수이고, m은 1 내지 10의 정수이다.
[화학식 2]
상기 화학식 2에서, X는 치환 또는 비치환된 C6~C40의 아릴렌기이며, n는 1 내지 10의 정수이고, m은 1 내지 10의 정수이며, p는 1 내지 5의 정수이고, q는 1 내지 5의 정수이다.Epoxidized polyphenylene oxide resins;
Inorganic filler;
Curing agent; And
A curing accelerator,
Wherein the epoxidized polyphenylene oxide resin is an epoxy-terminated polyphenylene oxide resin represented by the following formula (1) or a dicyclopentadiene epoxy-terminated polyphenylene oxide resin represented by the following formula (2).
[Chemical Formula 1]
X is a substituted or unsubstituted C 6 -C 40 arylene group, n is an integer of 1 to 10, and m is an integer of 1 to 10.
(2)
X is a substituted or unsubstituted C 6 -C 40 arylene group, n is an integer of 1 to 10, m is an integer of 1 to 10, p is an integer of 1 to 5, q Is an integer of 1 to 5.
상기 경화제는 하기 화학식 3으로 표시되는 알코올 말단 폴리페닐렌 옥사이드 수지 또는 하기 화학식 4로 표시되는 아민 말단 폴리페닐렌 옥사이드수지인 것을 특징으로 하는 수지 조성물.
[화학식 3]
상기 화학식 3에서, X는 치환 또는 비치환된 C6~C40의 아릴렌기이며, n는 1 내지 10의 정수이고, m은 1 내지 10의 정수이다.
[화학식 4]
상기 화학식 4에서, X는 치환 또는 비치환된 C6~C40의 아릴렌기이며, n는 1 내지 10의 정수이고, m은 1 내지 10의 정수이다.The method according to claim 1,
Wherein the curing agent is an alcohol-terminated polyphenylene oxide resin represented by the following formula (3) or an amine-terminated polyphenylene oxide resin represented by the following formula (4).
(3)
X is a substituted or unsubstituted C 6 -C 40 arylene group, n is an integer of 1 to 10, and m is an integer of 1 to 10.
[Chemical Formula 4]
X is a substituted or unsubstituted C 6 -C 40 arylene group, n is an integer of 1 to 10, and m is an integer of 1 to 10.
비스페놀 A형 에폭시 수지, 수소 첨가 비스페놀 A형 에폭시 수지, 비스페놀 F형 에폭시 수지, 비스페놀 S형 에폭시 수지, 노볼락형 에폭시 수지, 크레졸 노볼락형 에폭시 수지, 페놀 노볼락형 에폭시 수지, 디시클로펜타디엔형 에폭시 수지, 트리페닐메탄형 에폭시 수지, 나프탈렌형 에폭시 수지, 비페닐형 에폭시 수지 및 수소 첨가 비페닐형 에폭시 수지로 이루어진 군에서 선택된 1종 이상의 에폭시 수지를 더 포함하는 것을 특징으로 하는 수지 조성물.The method according to claim 1,
Bisphenol A type epoxy resin, hydrogenated bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, novolak type epoxy resin, cresol novolak type epoxy resin, phenol novolak type epoxy resin, dicyclopentadiene Wherein the resin composition further comprises at least one epoxy resin selected from the group consisting of epoxy resins, triphenylmethane type epoxy resins, naphthalene type epoxy resins, biphenyl type epoxy resins and hydrogenated biphenyl type epoxy resins.
난연제를 더 포함하는 것을 특징으로 하는 수지 조성물.The method according to claim 1,
The resin composition according to claim 1, further comprising a flame retardant.
전체 수지 조성물 100중량%를 기준으로,
상기 에폭시화 폴리페닐렌 옥사이드 수지 5 내지 60중량%;
상기 무기 필러 10 내지 50중량%;
상기 경화제 5 내지 40중량%; 및
상기 경화촉진제 0.01 내지 5중량%를 포함하는 것을 특징으로 하는 수지 조성물.The method according to claim 1,
Based on 100% by weight of the total resin composition,
5 to 60% by weight of the epoxidized polyphenylene oxide resin;
10 to 50% by weight of the inorganic filler;
5 to 40% by weight of the curing agent; And
And 0.01 to 5% by weight of the curing accelerator.
상기 섬유 기재에 함침되는 제1항, 제3항 내지 제6항 중 어느 한 항의 수지 조성물을 포함하는 프리프레그.Fiber substrates; And
A prepreg comprising the resin composition according to any one of claims 1 to 6 impregnated into the fiber substrate.
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| KR100835783B1 (en) * | 2007-06-26 | 2008-06-09 | 주식회사 두산 | Resin composition for printed circuit board, composite substrate and copper foil laminate using the same |
| KR100835784B1 (en) * | 2007-06-26 | 2008-06-09 | 주식회사 두산 | Resin composition for printed circuit board, composite substrate and copper foil laminate using the same |
| JP2009046631A (en) * | 2007-08-22 | 2009-03-05 | Asahi Kasei Chemicals Corp | Epoxidized polyphenylene ether resin and method for producing the same |
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| JP2010031087A (en) * | 2008-07-25 | 2010-02-12 | Asahi Kasei E-Materials Corp | Impregnating material for fibrous substrate, prepreg and fiber-reinforced composite material |
| TWI565750B (en) * | 2009-02-20 | 2017-01-11 | Ajinomoto Kk | Resin composition |
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| KR100835783B1 (en) * | 2007-06-26 | 2008-06-09 | 주식회사 두산 | Resin composition for printed circuit board, composite substrate and copper foil laminate using the same |
| KR100835784B1 (en) * | 2007-06-26 | 2008-06-09 | 주식회사 두산 | Resin composition for printed circuit board, composite substrate and copper foil laminate using the same |
| JP2009046631A (en) * | 2007-08-22 | 2009-03-05 | Asahi Kasei Chemicals Corp | Epoxidized polyphenylene ether resin and method for producing the same |
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