WO2021106931A1 - 末端変性ポリブタジエン、金属張積層板用樹脂組成物、プリプレグ、及び金属張積層板 - Google Patents
末端変性ポリブタジエン、金属張積層板用樹脂組成物、プリプレグ、及び金属張積層板 Download PDFInfo
- Publication number
- WO2021106931A1 WO2021106931A1 PCT/JP2020/043816 JP2020043816W WO2021106931A1 WO 2021106931 A1 WO2021106931 A1 WO 2021106931A1 JP 2020043816 W JP2020043816 W JP 2020043816W WO 2021106931 A1 WO2021106931 A1 WO 2021106931A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- metal
- resin composition
- clad laminate
- modified polybutadiene
- group
- Prior art date
Links
- 229920002857 polybutadiene Polymers 0.000 title claims abstract description 70
- 239000005062 Polybutadiene Substances 0.000 title claims abstract description 69
- 239000011342 resin composition Substances 0.000 title claims abstract description 38
- 229910052751 metal Inorganic materials 0.000 claims abstract description 13
- 239000002184 metal Substances 0.000 claims abstract description 13
- 239000011888 foil Substances 0.000 claims abstract description 6
- 239000000463 material Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 150000001451 organic peroxides Chemical class 0.000 claims description 9
- 238000009826 distribution Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000005647 linker group Chemical group 0.000 claims description 4
- 238000010030 laminating Methods 0.000 claims description 3
- 238000000465 moulding Methods 0.000 claims description 3
- 229910000679 solder Inorganic materials 0.000 abstract description 13
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- -1 aromatic vinyl compound Chemical class 0.000 description 24
- 229920005989 resin Polymers 0.000 description 22
- 239000011347 resin Substances 0.000 description 22
- 239000003063 flame retardant Substances 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 239000002966 varnish Substances 0.000 description 9
- 238000005227 gel permeation chromatography Methods 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- 239000011889 copper foil Substances 0.000 description 7
- 239000004744 fabric Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000001993 dienes Chemical class 0.000 description 6
- 239000011521 glass 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
- 125000002947 alkylene group Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000011256 inorganic filler Substances 0.000 description 4
- 229910003475 inorganic filler Inorganic materials 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000004745 nonwoven fabric Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-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
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- 239000004760 aramid Substances 0.000 description 2
- 229920003235 aromatic polyamide Polymers 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229920006026 co-polymeric resin Polymers 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229920006015 heat resistant resin Polymers 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- XFZRQAZGUOTJCS-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OP(O)(O)=O.NC1=NC(N)=NC(N)=N1 XFZRQAZGUOTJCS-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
- ACRQLFSHISNWRY-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-phenoxybenzene Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=CC=CC=C1 ACRQLFSHISNWRY-UHFFFAOYSA-N 0.000 description 1
- ORYGKUIDIMIRNN-UHFFFAOYSA-N 1,2,3,4-tetrabromo-5-(2,3,4,5-tetrabromophenoxy)benzene Chemical compound BrC1=C(Br)C(Br)=CC(OC=2C(=C(Br)C(Br)=C(Br)C=2)Br)=C1Br ORYGKUIDIMIRNN-UHFFFAOYSA-N 0.000 description 1
- DEIGXXQKDWULML-UHFFFAOYSA-N 1,2,5,6,9,10-hexabromocyclododecane Chemical compound BrC1CCC(Br)C(Br)CCC(Br)C(Br)CCC1Br DEIGXXQKDWULML-UHFFFAOYSA-N 0.000 description 1
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- OJMOMXZKOWKUTA-UHFFFAOYSA-N aluminum;borate Chemical compound [Al+3].[O-]B([O-])[O-] OJMOMXZKOWKUTA-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- KMQGNGCUCKMPLL-UHFFFAOYSA-N benzonitrile methylsulfinylmethane Chemical compound CS(=O)C.C(C1=CC=CC=C1)#N KMQGNGCUCKMPLL-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- HAISMSJTPGJFIP-UHFFFAOYSA-N butyl 4-tert-butyl-4,5,5-trimethylhexaneperoxoate Chemical compound CCCCOOC(=O)CCC(C)(C(C)(C)C)C(C)(C)C HAISMSJTPGJFIP-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 description 1
- 229920003244 diene elastomer Polymers 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical class CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000004843 novolac epoxy resin Substances 0.000 description 1
- 239000012188 paraffin wax Substances 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
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/06—Butadiene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
-
- 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
- B32B15/14—Layered products comprising a layer of metal next to a fibrous or filamentary layer
-
- 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
- B32B27/00—Layered products comprising a layer 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
- B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
- B32B5/02—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by structural features of a fibrous or filamentary layer
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/22—Incorporating nitrogen atoms into the molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/25—Incorporating silicon atoms into the molecule
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides
-
- 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
- H05K1/034—Organic insulating material consisting of one material containing halogen
-
- 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
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
- H05K1/0366—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement reinforced, e.g. by fibres, fabrics
-
- 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
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
- H05K1/0373—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement containing additives, e.g. fillers
-
- 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
- B32B2250/00—Layers arrangement
- B32B2250/02—2 layers
-
- 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
- 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
-
- 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
- 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
-
- 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
- B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
- B32B2262/10—Inorganic fibres
- B32B2262/101—Glass fibres
-
- 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
- B32B2305/00—Condition, form or state of the layers or laminate
- B32B2305/07—Parts immersed or impregnated in a matrix
- B32B2305/076—Prepregs
-
- 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
- B32B2307/20—Properties of the layers or laminate having particular electrical or magnetic properties, e.g. piezoelectric
- B32B2307/204—Di-electric
-
- 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
-
- 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
- B32B2307/70—Other properties
- B32B2307/732—Dimensional properties
-
- 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
- B32B2307/70—Other properties
- B32B2307/748—Releasability
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2810/00—Chemical modification of a polymer
- C08F2810/40—Chemical modification of a polymer taking place solely at one end or both ends of the polymer backbone, i.e. not in the side or lateral chains
-
- 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
- C08J2309/00—Characterised by the use of homopolymers or copolymers of conjugated diene hydrocarbons
-
- 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
- C08J2315/00—Characterised by the use of rubber derivatives
-
- 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
- C08J2347/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Derivatives of such polymers
-
- 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
- H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
- H05K2201/02—Fillers; Particles; Fibers; Reinforcement materials
- H05K2201/0203—Fillers and particles
- H05K2201/0206—Materials
- H05K2201/0209—Inorganic, non-metallic particles
-
- 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
- H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
- H05K2201/02—Fillers; Particles; Fibers; Reinforcement materials
- H05K2201/0203—Fillers and particles
- H05K2201/0206—Materials
- H05K2201/0215—Metallic fillers
-
- 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
- H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
- H05K2201/02—Fillers; Particles; Fibers; Reinforcement materials
- H05K2201/0275—Fibers and reinforcement materials
- H05K2201/0278—Polymeric fibers
-
- 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
- H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
- H05K2201/02—Fillers; Particles; Fibers; Reinforcement materials
- H05K2201/0275—Fibers and reinforcement materials
- H05K2201/0284—Paper, e.g. as reinforcement
-
- 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
- H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
- H05K2201/02—Fillers; Particles; Fibers; Reinforcement materials
- H05K2201/0275—Fibers and reinforcement materials
- H05K2201/029—Woven fibrous reinforcement or textile
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/02—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding
- H05K3/022—Processes for manufacturing precursors of printed circuits, i.e. copper-clad substrates
Definitions
- the present invention relates to terminally modified polybutadiene.
- the present invention also relates to a resin composition for a metal-clad laminate containing the terminal-modified polybutadiene, a prepreg in which a base material is impregnated with the metal-clad laminate resin composition, and a metal-clad laminate using the prepreg.
- the present application claims priority to Japanese Patent Application No. 2019-216308 filed on November 29, 2019, the contents of which are incorporated herein by reference.
- a material called a copper-clad laminate is used for electronic devices such as personal computers and mobile terminals.
- a copper-clad laminate is a material having a laminated structure, which is produced by impregnating a glass cloth made of glass fiber with a varnish containing a resin such as epoxy as a main component and then pasting copper foils on both sides thereof.
- resin materials used for copper-clad laminates are required to have dielectric properties such as low dielectric constant and low dielectric loss tangent required for high-speed communication. There is. In addition, high adhesiveness to copper foil and solder heat resistance are also required.
- Patent Document 1 Various resin compositions have been proposed as resin compositions that can be used for copper-clad laminates.
- Patent Document 1 (A) a copolymer resin having a structural unit derived from an aromatic vinyl compound and a structural unit derived from maleic anhydride, and (B) an epoxy-modified polybutadiene having hydroxyl groups at both ends of the molecule.
- C An active ester compound
- D a thermosetting resin composition containing at least one selected from the group consisting of a maleimide compound and a modified product thereof have been proposed.
- Patent Document 2 a copolymer resin having (A) a structural unit derived from an aromatic vinyl compound and a structural unit derived from maleic anhydride, (B) an epoxy-modified polybutadiene having a hydroxyl group, and (C) a maleimide compound.
- a thermosetting resin composition containing the above has been proposed.
- an epoxidized polybutadiene compound is an essential component, and for example, a polyfunctional cresol novolac epoxy resin, a polyfunctional brominated epoxy resin, a triazine-modified cresol novolac resin, and a large amount of flame-retardant inorganic substances.
- a flame-retardant epoxy resin composition characterized by blending a filler or the like has been proposed.
- Patent Document 4 proposes a resin composition having excellent heat resistance, dielectric properties, and water absorption by using a cyanate resin and an epoxy-modified polybutadiene resin in combination.
- Patent Document 5 (A) a specific benzocyclobutene resin or a prepolymer thereof, (B) an epoxy-modified polybutadiene resin, (C) a halogenated epoxy resin, and (D) a curing agent having a reactive group that reacts with an epoxy group.
- a heat-resistant resin composition has been proposed, which comprises the above as an essential component.
- Patent Document 6 contains (A) a specific benzocyclobutene resin or a prepolymer thereof, (B) an epoxy-modified polybutadiene resin, and (C) an aromatic amine compound containing one or more atoms of halogen in the molecule as essential components.
- a heat-resistant resin composition characterized by the above has been proposed.
- Patent Document 7 a curable resin composition having a small thermal expansion coefficient containing a copolymer composed of a conjugated diene polymer block and an N-substituted maleimide polymer block, a thermosetting resin, and silicon-modified polybutadiene is used. Proposed.
- Patent Document 8 proposes a copper foil adhesive for copper-clad laminates in which a resin composition containing a polyvinyl butyral resin, an epoxy resin and a curing agent thereof, and an amino resin is blended with an acidic curing agent that causes a cross-linking reaction thereof. ..
- Patent Document 9 describes a linear modified diene polymer having a functional group represented by the following formula (1) at only one end and having an average number of functional groups of 0.8 to 1 per molecule. Is described. By including the modified diene polymer in the rubber composition, it seems that the dispersed state of the filler in the crosslinked product obtained from the composition can be made into an ideal state for improving the physical properties.
- Patent Document 10 describes a silane-modified polybutadiene that can be obtained by reacting a hydroxyl-terminal polybutadiene produced by free radical polymerization with one or more kinds of organic silane compounds.
- the silane-modified polybutadiene seems to be able to improve the rolling resistance of the diene rubber tire.
- Patent Document 11 describes a modified liquid diene polymer having at least one group represented by the general formula (1) in the molecule and having a main chain consisting of a diene polymer chain having a number average molecular weight of 4000 to 50,000. ing.
- the modified liquid diene polymer it seems that it is possible to provide a rubber composition capable of achieving both wet road braking performance and rolling resistance performance.
- Patent Document 12 describes a polymer silane coupling agent in which mercaptosilane is added to a butadiene polymer. Further, a rubber composition for an automobile tire tread in which the polymer silane coupling agent and a filler composed of silica and carbon black are blended in a conjugated elastomer has been proposed.
- JP-A-2018-165340 JP-A-2017-115020 Japanese Unexamined Patent Publication No. 2005-2226 Japanese Unexamined Patent Publication No. 2002-265782 JP-A-2002-226680 Japanese Unexamined Patent Publication No. 2002-226681 Japanese Unexamined Patent Publication No. 6-145380 Japanese Unexamined Patent Publication No. 6-128547 Japanese Patent No. 6581746 Special Table 2018-515658 Japanese Unexamined Patent Publication No. 2015-83649 Japanese Unexamined Patent Publication No. 2000-344949
- the metal-clad laminate manufactured from the conventionally known resin composition for metal-clad laminate may not have sufficient adhesiveness to metal foil, solder heat resistance, and insulating property.
- An object of the present invention is to provide a novel resin composition for a metal-clad laminate capable of producing a metal-clad laminate having excellent adhesiveness to a metal foil, solder heat resistance, and insulating properties. ..
- the present inventor contains a specific trialkoxysilyl group at both ends of polybutadiene having a ratio of 1,2 bond structure of 70 to 99 mol% in all repeating units.
- a terminally modified polybutadiene having a structure was found.
- a resin composition for a metal-clad laminate containing the terminal-modified polybutadiene was found.
- a prepreg and a metal-clad laminate using the resin composition for a metal-clad laminate was found.
- Equation (I) The repeating unit represented by and equation (II)
- the ratio of the repeating unit represented by the formula (I) is 70 to 99 mol% in all the repeating units including the repeating unit represented by the formula (III) at both ends of the polybutadiene.
- R 1 , R 2 , and R 3 independently represent an alkoxy group, an aryloxy group, an alkyl group, or an aryl group
- X indicates a linking group
- * indicates a binding site.
- at least one of R 1, R 2 and R 3 are alkoxy or aryloxy group.
- terminal modified polybutadiene having a structure represented by.
- the terminal-modified polybutadiene according to (1) which has a weight average molecular weight (Mw) of 1,000 to 100,000.
- the terminal-modified polybutadiene according to (1) or (2) which has a molecular weight distribution (Mw / Mn) of 1.00 to 3.00.
- the resin composition for a metal-clad laminate according to (5) which contains 1 to 5 parts by weight of an organic peroxide with respect to 100 parts by weight of terminal-modified polybutadiene.
- the resin composition for a metal-clad laminate of the present invention it is possible to produce a metal-clad laminate having excellent adhesiveness to a metal foil, solder heat resistance, and insulation.
- the terminal-modified polybutadiene of the present invention has a structure represented by the following formula (III) at both ends of the polybutadiene.
- polybutadiene is a polymer compound obtained by polymerizing butadiene.
- polybutadiene is a repeating unit represented by the following formula (I) (hereinafter, may be referred to as "1,2-bond”) and the following formula (II) (hereinafter, "1,4"). It has a repeating unit represented by (sometimes referred to as "bond”).
- the proportion of the repeating unit represented by the formula (I) in the "polybutadiene" constituting the terminal-modified polybutadiene of the present invention is preferably 70 to 99 mol%, preferably 75 to 99 mol%. Is more preferable, and 80 to 99 mol% is further preferable.
- "Polybutadiene” is a repeating unit other than the repeating unit represented by the formula (I) and the repeating unit represented by the formula (II), such as a repeating unit obtained by hydrogenating the repeating unit represented by the formula (I) or a repeating unit.
- the repeating unit represented by the formula (II) may contain a hydrogenated repeating unit.
- R 1 , R 2 , and R 3 independently represent an alkoxy group, an aryloxy group, an alkyl group, or an aryl group, respectively. However, at least one of R 1 , R 2 and R 3 is an alkoxy group or an aryloxy group. The presence of at least one alkoxy group or aryloxy group in R 1 , R 2 and R 3 forms a covalent bond with a hydroxyl group on the metal surface by a condensation reaction. As a result, the terminal-modified polybutadiene of the present invention exhibits high adhesiveness to metals.
- the alkoxy groups in R 1 , R 2 and R 3 include methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group and t-butoxy group. And so on. Of these, C1 to 6 alkoxy groups are preferable, and methoxy groups and ethoxy groups are more preferable.
- Examples of the aryloxy group in R 1 , R 2 and R 3 include a phenoxy group and a naphthoxy group. Of these, a C6 to 10 aryloxy group is preferable, and a phenoxy group is more preferable.
- Alkyl groups in R 1 , R 2 , and R 3 include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, and t-butyl group. , N-pentyl group, n-hexyl group and the like. Of these, a C1 to 6 alkyl group is preferable, and a methyl group and an ethyl group are more preferable.
- Examples of the aryl group in R 1 , R 2 and R 3 include a phenyl group and a naphthyl group. Of these, a C6 to 10 aryl group is preferable, and a phenyl group is more preferable.
- X represents a linking group.
- the linking group include an alkylene group and an alkylene-O-alkylene group.
- the alkylene group include methylene, ethylene, propane-1,3-diyl, propane-1,2-diyl, butane-1,4-diyl, butane-2,3-diyl, pentane-1,5-diyl and pentane. Examples thereof include -1,4-diyl, 2-methylbutane-1,4-diyl, hexane-1,6-diyl, octane-1,8-diyl, and decane-1,10-diyl.
- the alkylene-O-alkylene group means a group in which an alkylene group and an alkylene group are bonded via an —O— bond.
- Examples of the alkylene-O-alkylene group include an ethylene-O-ethylene group and an ethylene-O-propane-1,3-diyl group.
- the molecular weight of the terminally modified polybutadiene of the present invention is not particularly limited, but the number average molecular weight (Mn) is 1,000 to 100,000, 1,000 to 80,000, 1,000 to 70,000, 1,000 to 1,000.
- Mn number average molecular weight
- the range of 60,000, 1,000 to 50,000, 1,000 to 40,000, 1,000 to 30,000, 1,000 to 20,000, 1,000 to 10,000 can be selected. it can.
- the molecular weight distribution (Mw / Mn) of the terminally modified polybutadiene of the present invention is not particularly limited, but 1.00 to 5.00, 1.00 to 4.00, 1.00 to 3.00, and 1.00 to 2.
- the range of 00 can be selected.
- the weight average molecular weight (Mw) and the number average molecular weight (Mn) are values obtained by converting data measured by gel permeation chromatography (GPC) using tetrahydrofuran as a solvent based on the molecular weight of standard polystyrene.
- the terminal-modified polybutadiene of the present invention can be produced by reacting both terminal hydroxyl-modified polybutadiene (1) with the isocyanate compound (2) in a solvent or under solvent-free conditions.
- R 1 , R 2 , R 3 , and X are the same as those described in the formula (III).
- hydroxyl-modified polybutadiene As the hydroxyl-modified polybutadiene at both ends, a commercially available product can be used.
- Commercially available products with both-terminal hydroxyl-modified polybutadiene include NISSO-PB G-1000 (manufactured by Nippon Soda Co., Ltd.), NISSO-PB G-2000 (manufactured by Nippon Soda Co., Ltd.), and NISSO-PB G-3000 (manufactured by Nippon Soda Co., Ltd.). (Made by Co., Ltd.) and the like. These can be used alone or in combination of two or more.
- the reaction is preferably carried out without using a metal catalyst.
- the solvent used in the reaction is an aromatic hydrocarbon such as benzene, toluene or xylene; an ester solvent such as methyl acetate, ethyl acetate or n-propyl acetate; N, N-dimethylformamide.
- Amide solvents such as N, N-dimethylacetamide and N-methylpyrrolidone; ether solvents such as diethyl ether, tetrahydrofuran, 1,2-dimethoxyethane, 1,4-dioxane; nitrile solvents such as acetonitrile and benzonitrile Dimethylsulfoxide; Examples thereof include phosphoric acid amide-based solvents such as hexamethylphospholastriadide (HMPT) and hexamethylphosphoroamide (HMPA).
- the reaction temperature is usually in the range of 0 ° C. to 100 ° C., preferably room temperature to 80 ° C., and the reaction is usually completed in a few minutes to a few hours.
- the resin composition for a metal-clad laminate of the present invention contains the terminal-modified polybutadiene of the present invention.
- the content of the terminal-modified polybutadiene in the resin composition for a metal-clad laminate of the present invention is not particularly limited, and may be 10 to 90% by weight based on the total weight of the resin composition for a metal-clad laminate. Can be done.
- the resin composition for a metal-clad laminate of the present invention may contain an organic peroxide.
- the content of the organic peroxide is not particularly limited, but it is preferable that the content of the organic peroxide is 1 to 5 parts by weight with respect to 100 parts by weight of the terminal-modified polybutadiene.
- organic peroxides examples include dicumyl peroxide, di-t-butylperoxy-3,3,5-trimethylcyclohexane, ⁇ , ⁇ '-di-t-butylperoxydip-diisopyropyrbenzene, n-Butyl-4,4-bis-t-butylperoxyvalerate, t-butylperoxybenzoate, t-butylperoxyisopropylcarbonate, 2,5-dimethyl-2,5-di (t-butylper) Oxy) hexane and the like can be mentioned. Of these, dicumyl peroxide is preferable.
- additives can be appropriately added to the resin composition for a metal-clad laminate of the present invention as long as the effects of the present invention are not impaired.
- additives include cross-linking agents, flame retardants, inorganic fillers, solvents and the like.
- the cross-linking agent is not particularly limited, and examples thereof include dibenylbenzene and triallyl isocyanurate.
- the amount thereof is not particularly limited, and examples thereof include an amount of 1 to 50% by weight based on the terminal-modified polybutadiene of the present invention.
- the flame retardant is not particularly limited, and examples thereof include halogen-based flame retardants such as bromine-based flame retardants and phosphorus-based flame retardants.
- halogen-based flame retardants such as bromine-based flame retardants and phosphorus-based flame retardants.
- examples of the halogen-based flame retardant include brominated flame retardants such as pentabromodiphenyl ether, octabromodiphenyl ether, decabromodiphenyl ether, tetrabromobisphenol A and hexabromocyclododecane, and chlorine-based flame retardants such as chlorinated paraffin. it can.
- Phosphate-based flame retardants include phosphoric acid esters such as condensed phosphoric acid ester and cyclic phosphoric acid ester, phosphazene compounds such as cyclic phosphazene compounds, phosphinate-based flame retardants such as dialkylphosphinic acid aluminum salt, melamine phosphate, and polyphosphorus. Examples thereof include melamine-based flame retardants such as phosphate melamine.
- the amount thereof is not particularly limited, and examples thereof include an amount of 1 to 20% by weight based on the terminal-modified polybutadiene of the present invention.
- the inorganic filler examples include silica, alumina, talc, aluminum hydroxide, magnesium hydroxide, titanium oxide, mica, aluminum borate, barium sulfate, and calcium carbonate.
- the amount to be added is not particularly limited, and examples thereof include an amount of 10 to 150% by weight based on the terminal-modified polybutadiene of the present invention.
- the method for producing the resin composition for a metal-clad laminate of the present invention is not particularly limited.
- a method of adding other components to the terminal-modified polybutadiene of the present invention and then kneading with a kneader can be mentioned.
- the resin composition for a metal-clad laminate of the present invention may be prepared and used in a varnish shape for the purpose of impregnating a base material (fibrous base material) for forming the prepreg.
- a resin varnish is prepared, for example, as follows.
- each component that can be dissolved in an organic solvent is put into an organic solvent and dissolved. At this time, if necessary, it may be heated. After that, a component that is used as needed and does not dissolve in an organic solvent, for example, an inorganic filler, is added and dispersed using a ball mill, a bead mill, a planetary mixer, a roll mill, or the like until a predetermined dispersion state is obtained. This prepares a resin varnish.
- Examples of a method for producing a prepreg using the obtained resin varnish include a method in which the obtained resin varnish is impregnated into a fibrous base material and then dried.
- fibrous base material used in producing the prepreg include glass cloth, aramid cloth, polyester cloth, glass non-woven fabric, aramid non-woven fabric, polyester non-woven fabric, pulp paper, linter paper and the like. ..
- a semi-cured (B stage) prepreg can be obtained by heating a fibrous substrate impregnated with a resin varnish under desired heating conditions, for example, 80 to 170 ° C. for 1 to 10 minutes to remove the solvent. it can.
- Metal-clad laminate By stacking one or more of the obtained prepregs, further stacking metal foils such as copper foil on both upper and lower sides or one side, and laminating and integrating them by heat and pressure molding, double-sided metal leaf covering or one side. A metal foil-covered laminate can be produced.
- the heating and pressurizing conditions can be appropriately set depending on the thickness of the laminated board to be manufactured, the type of the resin composition of the prepreg, and the like. For example, the temperature can be 170 to 210 ° C., the pressure can be 1.5 to 4.0 MPa, and the time can be 60 to 150 minutes.
- the weight average molecular weight (Mw) and the number average molecular weight (Mn) are values obtained by converting data measured by gel permeation chromatography (GPC) using tetrahydrofuran as a solvent based on the molecular weight of standard polystyrene.
- the weight average molecular weight (Mw) and the number average molecular weight (Mn) are values obtained by converting data measured by gel permeation chromatography (GPC) using tetrahydrofuran as a solvent based on the molecular weight of standard polystyrene.
- the weight average molecular weight (Mw) and the number average molecular weight (Mn) are values obtained by converting data measured by gel permeation chromatography (GPC) using tetrahydrofuran as a solvent based on the molecular weight of standard polystyrene.
- Example 1 The terminal-modified polybutadiene A, the solvent, and the organic peroxide were mixed so as to have the ratio shown in Table 1 to obtain a varnish.
- the glass cloth was dipped in this varnish and the glass cloth was impregnated with the resin. Then, the varnish-impregnated glass cloth was dried at 150 ° C. for 10 minutes to obtain a prepreg.
- a rough surface of a copper foil having a thickness of 18 ⁇ m was attached to one side of the prepreg. Then, it was heated at 195 ° C. for 120 minutes under a pressure of 3 MPa to obtain a metal-clad laminate.
- solder heat resistance Measured according to JIS C 6481. The copper-clad laminate was immersed in the solder at 260 ° C. for 2 minutes, and the solder heat resistance was evaluated by observing the peeling of the copper foil. Those that did not peel off were marked with " ⁇ ", and those that did peel off were marked with "x”. The results are shown in Table 2.
- Example 2 A metal-clad laminate was produced, the dielectric constant and the dielectric loss tangent were measured, and the peel strength and solder heat resistance were tested in the same manner as in Example 1, except that the resin component was end-modified polybutadiene B. The results are shown in Table 2.
- Comparative Example 1 A metal-clad laminate was prepared, the dielectric constant and the dielectric loss tangent were measured, and the peel strength and solder heat resistance were tested in the same manner as in Example 1, except that the resin component was end-modified polybutadiene C. The results are shown in Table 2.
- Comparative Example 2 Similar to Example 1, preparation of a metal-clad laminate, measurement of dielectric constant and dielectric loss tangent, peel strength, and the like, except that the resin component is NISSO-PB B-1000 having no functional group at the end. A solder heat resistance test was conducted. The results are shown in Table 2.
- Comparative Example 3 Similar to Example 1, preparation of a metal-clad laminate, measurement of dielectric constant and dielectric loss tangent, peel strength, and the like, except that the resin component is NISSO-PB B-3000 having no functional group at the end. A solder heat resistance test was conducted. The results are shown in Table 2.
- Comparative Example 4 Similar to Example 1, fabrication of a metal-clad laminate, measurement of dielectric constant and dielectric loss tangent, peel strength, and solder heat resistance, except that the resin component is 1,4-polybutadiene synthesized in Production Example 3. A sex test was performed. The results are shown in Table 2.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- General Chemical & Material Sciences (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Laminated Bodies (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Reinforced Plastic Materials (AREA)
Abstract
Description
例えば、特許文献9には、一方の末端のみに下記式(1)で示される官能基を有し、1分子当たりの平均官能基数が0.8~1である直鎖状変性ジエン系重合体が記載されている。該変性ジエン系重合体をゴム組成物に含ませることにより、その組成物から得られる架橋物中のフィラーの分散状態を物性向上のために理想的な状態にできるようである。
(1)式(I)
(2)重量平均分子量(Mw)が、1,000~100,000である(1)に記載の末端変性ポリブタジエン。
(3)分子量分布(Mw/Mn)が、1.00~3.00である(1)または(2)に記載の末端変性ポリブタジエン。
(4)(1)~(3)いずれかに記載の末端変性ポリブタジエンを含有する金属張積層板用樹脂組成物。
(5)さらに、有機過酸化物を含有する(4)に記載の金属張積層板用樹脂組成物。
(6)末端変性ポリブタジエン100重量部に対して、有機過酸化物を1~5重量部含有する(5)に記載の金属張積層板用樹脂組成物。
(7)(4)~(6)いずれかに記載の金属張積層板用樹脂組成物が基材に含浸されたプリプレグ。
(8)(7)に記載のプリプレグと金属箔とを積層して成形することにより製造される金属張積層板。
本発明の末端変性ポリブタジエンは、ポリブタジエンの両末端に下記式(III)で表される構造を有する。本発明において「ポリブタジエン」とは、ブタジエンを重合した高分子化合物である。本発明において「ポリブタジエン」は、下記式(I)で表される繰り返し単位(以下、「1,2-結合」と記載する場合がある)と、下記式(II)(以下、「1,4-結合」と記載する場合がある)で表される繰り返し単位を有する。本発明の末端変性ポリブタジエンを構成する「ポリブタジエン」は、全繰り返し単位中、式(I)で表される繰り返し単位の割合が70~99モル%であるのが好ましく、75~99モル%であるのがより好ましく、80~99モル%であるのがさらに好ましい。「ポリブタジエン」は、式(I)で表される繰り返し単位および式(II)で表される繰り返し単位以外の繰り返し単位として、式(I)で表される繰り返し単位を水素添加した繰り返し単位や、式(II)で表される繰り返し単位を水素添加した繰り返し単位を含んでいてもよい。
アルキレン基としては、メチレン、エチレン、プロパン-1,3-ジイル、プロパン-1,2-ジイル、ブタン-1,4-ジイル、ブタン-2,3-ジイル、ペンタン-1,5-ジイル、ペンタン-1,4-ジイル、2-メチルブタン-1,4-ジイル、ヘキサン-1,6-ジイル、オクタン-1,8-ジイル、デカン-1,10-ジイルなどを挙げることができる。これらのうち、C1~10のアルキレン基が好ましい。
アルキレン-O-アルキレン基とは、アルキレン基とアルキレン基が-O-結合を介して結合している基を意味する。アルキレン-O-アルキレン基としては、エチレン-O-エチレン基、エチレン-O-プロパン-1,3-ジイル基などを挙げることができる。
次に、本発明の末端変性ポリブタジエンの製造方法について説明する。
両末端水酸基変性ポリブタジエン(1)と、イソシアネート化合物(2)を溶媒中で、あるいは無溶媒条件下で、反応させることにより本発明の末端変性ポリブタジエンを製造することができる。
反応温度は、通常0℃~100℃、好ましくは室温~80℃の範囲であり、反応は通常数分~数時間で完結する。
本発明の金属張積層板用樹脂組成物は、本発明の末端変性ポリブタジエンを含有する。
本発明の金属張積層板用樹脂組成物中の末端変性ポリブタジエンの含有量は、特に限定されないが、金属張積層板用樹脂組成物の全重量に対して、10~90重量%などを挙げることができる。
本発明の金属張積層板用樹脂組成物には、本発明の効果を損なわない範囲で適宜その他の添加剤を加えることができる。その他の添加剤としては、例えば、架橋剤、難燃剤、無機充填材、溶剤などを挙げることができる。
架橋剤を添加する場合、その添加量は特に限定されないが、本発明の末端変性ポリブタジエンに対して1~50重量%となる量を挙げることができる。
ハロゲン系難燃剤としては、ペンタブロモジフェニルエーテル、オクタブロモジフェニルエーテル、デカブロモジフェニルエーテル、テトラブロモビスフェノールA、ヘキサブロモシクロドデカンなどの臭素系難燃剤や、塩素化パラフィンなどの塩素系難燃剤などを挙げることができる。
リン系難燃剤としては、縮合リン酸エステル、環状リン酸エステル等のリン酸エステル、環状ホスファゼン化合物などのホスファゼン化合物、ジアルキルホスフィン酸アルミニウム塩などのホスフィン酸塩系難燃剤、リン酸メラミン、及びポリリン酸メラミンなどのメラミン系難燃剤などを挙げることができる。
難燃剤を添加する場合、その添加量は特に限定されないが、本発明の末端変性ポリブタジエンに対して1~20重量%となる量を挙げることができる。
無機充填材を添加する場合、その添加量は特に限定されないが、本発明の末端変性ポリブタジエンに対して、10~150重量%となる量を挙げることができる。
本発明の金属張積層板用樹脂組成物は、プリプレグを製造する際には、プリプレグを形成するための基材(繊維質基材)に含浸する目的でワニス状に調製して用いられることが多い。このような樹脂ワニスは、例えば、以下のようにして調製される。
得られたプリプレグを一枚または複数枚重ね、さらにその上下の両面又は片面に銅箔等の金属箔を重ね、これを加熱加圧成形して積層一体化することによって、両面金属箔張り又は片面金属箔張りの積層体を作製することができる。
加熱加圧条件は、製造する積層板の厚みやプリプレグの樹脂組成物の種類等により適宜設定することができる。例えば、温度を170~210℃、圧力を1.5~4.0MPa、時間を60~150分間とすることができる。
製造例1
200mLフラスコにNISSO-PB G-1000(水酸基価73.0mgKOH/g)を100g入れた。そこにG-1000の水酸基価のモル数に対して0.9倍モルとなるように3-イソシアナトプロピルトリメトキシシランを24.04g加えた。これを十分に撹拌しながら60℃まで加温し、12時間反応させることで末端変性ポリブタジエンAを得た。得られた末端変性ポリブタジエンAは数平均分子量(Mn)が3200で且つ分子量分布(Mw/Mn)が2.24であった。なお、重量平均分子量(Mw)および数平均分子量(Mn)は、テトラヒドロフランを溶媒とするゲルパーミエーションクロマトグラフィー(GPC)にて測定したデータを標準ポリスチレンの分子量に基づいて換算した値である。
200mLフラスコにNISSO-PB G-3000(水酸基価31.0mgKOH/g)を100g入れた。そこにG-3000の水酸基価のモル数に対して0.9倍モルとなるように3-イソシアナトプロピルトリメトキシシランを10.21g加えた。これを十分に撹拌しながら60℃まで加温し、12時間反応させることで末端変性ポリブタジエンBを得た。得られた末端変性ポリブタジエンBは数平均分子量(Mn)が6700で且つ分子量分布(Mw/Mn)が1.57であった。なお、重量平均分子量(Mw)および数平均分子量(Mn)は、テトラヒドロフランを溶媒とするゲルパーミエーションクロマトグラフィー(GPC)にて測定したデータを標準ポリスチレンの分子量に基づいて換算した値である。
遠藤剛編、高分子の合成(上)、第1版、講談社、2010を参考にラジカル開始剤を用いて両末端水酸基変性1,4-ポリブタジエンを合成した。合成した1,4-ポリブタジエンはMnが約5000、1,2-ビニル率が約20%、水酸基価が約48mgKOH/gであった。
200mLフラスコに上記で合成した1,4-ポリブタジエン(水酸基価48.0mg KOH/g)を100g入れた。そこに1,4-ポリブタジエンの水酸基価のモル数に対して0.9倍モルとなるように3-イソシアナトプロピルトリメトキシシランを15.81g加えた。これを十分に撹拌しながら60℃まで加温し、12時間反応させることで末端変性ポリブタジエンCを得た。得られた末端変性ポリブタジエンCは数平均分子量(Mn)が6000で且つ分子量分布(Mw/Mn)が2.10であった。なお、重量平均分子量(Mw)および数平均分子量(Mn)は、テトラヒドロフランを溶媒とするゲルパーミエーションクロマトグラフィー(GPC)にて測定したデータを標準ポリスチレンの分子量に基づいて換算した値である。
実施例1
表1に示す割合になるように末端変性ポリブタジエンA、溶剤、有機過酸化物を混合し、ワニスを得た。このワニスにガラスクロスを浸漬してガラスクロスに樹脂を含浸させた。その後ワニス含浸ガラスクロスを150℃で10分間乾燥させプリプレグを得た。このプリプレグの片面に厚さ18μmの銅箔の粗面を張り付けた。その後3MPaの加圧下で195℃、120分間加熱を行うことで金属張積層板を得た。
誘電率・誘電正接は樹脂単独で測定した。測定周波数5GHzにおける誘電率および誘電正接をプローブ法で測定した。結果を表2に示した。
JIS C 6481にしたがって測定した。金属張積層板について銅箔の90℃剥離試験を行うことにより、ピール強度を測定した。結果を表2に示した。
JIS C 6481にしたがって測定した。260℃のはんだ中に銅張積層板を2分間浸漬し、銅箔の剥がれを観察することによりはんだ耐熱性を評価した。剥がれがなかったものを「○」、剥がれが生じたものを「×」とした。結果を表2に示した。
樹脂成分を末端変性ポリブタジエンBとすることを除いて、実施例1と同様に金属張積層板の作製、および、誘電率・誘電正接の測定、ピール強度、はんだ耐熱性の試験を行った。結果を表2に示した。
樹脂成分を末端変性ポリブタジエンCとすることを除いて、実施例1と同様に、金属張積層板の作製および誘電率・誘電正接の測定、ピール強度、はんだ耐熱性の試験を行った。結果を表2に示した。
樹脂成分を末端に官能基を持たないNISSO-PB B-1000とすることを除いて、実施例1と同様に、金属張積層板の作製、および、誘電率・誘電正接の測定、ピール強度、はんだ耐熱性の試験を行った。結果を表2に示した。
樹脂成分を末端に官能基を持たないNISSO-PB B-3000とすることを除いて、実施例1と同様に、金属張積層板の作製、および、誘電率・誘電正接の測定、ピール強度、はんだ耐熱性の試験を行った。結果を表2に示した。
樹脂成分を製造例3で合成した1,4-ポリブタジエンとすることを除いて、実施例1と同様に、金属張積層板の作製、および、誘電率・誘電正接の測定、ピール強度、はんだ耐熱性の試験を行った。結果を表2に示した。
Claims (8)
- 重量平均分子量(Mw)が、1,000~100,000である請求項1に記載の末端変性ポリブタジエン。
- 分子量分布(Mw/Mn)が、1.00~3.00である請求項1または2に記載の末端変性ポリブタジエン。
- 請求項1~3いずれか1項に記載の末端変性ポリブタジエンを含有する金属張積層板用樹脂組成物。
- さらに、有機過酸化物を含有する請求項4に記載の金属張積層板用樹脂組成物。
- 末端変性ポリブタジエン100重量部に対して、有機過酸化物を1~5重量部含有する請求項5に記載の金属張積層板用樹脂組成物。
- 請求項4~6いずれか1項に記載の金属張積層板用樹脂組成物が基材に含浸されたプリプレグ。
- 請求項7に記載のプリプレグと金属箔とを積層して成形することにより製造される金属張積層板。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US17/779,320 US20230002532A1 (en) | 2019-11-29 | 2020-11-25 | Terminally modified polybutadiene, resin composition for metal-clad laminates, prepreg, and metal-clad laminate |
KR1020227016805A KR20220083802A (ko) | 2019-11-29 | 2020-11-25 | 말단 변성 폴리부타디엔, 금속 피복 적층판용 수지 조성물, 프리프레그, 및 금속 피복 적층판 |
JP2021561453A JP7307813B2 (ja) | 2019-11-29 | 2020-11-25 | 末端変性ポリブタジエン、金属張積層板用樹脂組成物、プリプレグ、及び金属張積層板 |
EP20894047.8A EP4067077A4 (en) | 2019-11-29 | 2020-11-25 | FINALLY MODIFIED POLYBUTADIENE, RESIN COMPOSITION FOR METAL BACKED LAMINATES, PREPREG AND METAL BACKED LAMINATES |
CN202080081141.4A CN114729064B (zh) | 2019-11-29 | 2020-11-25 | 末端改性聚丁二烯、覆金属层叠板用树脂组合物、预浸料坯及覆金属层叠板 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2019-216308 | 2019-11-29 | ||
JP2019216308 | 2019-11-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2021106931A1 true WO2021106931A1 (ja) | 2021-06-03 |
Family
ID=76129493
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2020/043816 WO2021106931A1 (ja) | 2019-11-29 | 2020-11-25 | 末端変性ポリブタジエン、金属張積層板用樹脂組成物、プリプレグ、及び金属張積層板 |
Country Status (7)
Country | Link |
---|---|
US (1) | US20230002532A1 (ja) |
EP (1) | EP4067077A4 (ja) |
JP (1) | JP7307813B2 (ja) |
KR (1) | KR20220083802A (ja) |
CN (1) | CN114729064B (ja) |
TW (1) | TWI829981B (ja) |
WO (1) | WO2021106931A1 (ja) |
Citations (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61121699A (ja) * | 1984-11-19 | 1986-06-09 | Matsushita Electric Ind Co Ltd | 圧電スピ−カ |
JPS62198111A (ja) * | 1986-02-25 | 1987-09-01 | 東レ株式会社 | 金属蒸着フイルム及びコンデンサ− |
JPH06128547A (ja) | 1991-08-29 | 1994-05-10 | Hitachi Chem Co Ltd | 銅張積層板用銅箔接着剤 |
JPH06145380A (ja) | 1992-11-13 | 1994-05-24 | Nec Corp | プリプレグ及び銅張積層板 |
JP2000344949A (ja) | 1999-03-31 | 2000-12-12 | Nippon Mitsubishi Oil Corp | 自動車タイヤトレッド用ゴム組成物 |
JP2002226681A (ja) | 2001-02-02 | 2002-08-14 | Sumitomo Bakelite Co Ltd | 耐熱性樹脂組成物、これを用いたプリプレグ及び積層板 |
JP2002226680A (ja) | 2001-02-02 | 2002-08-14 | Sumitomo Bakelite Co Ltd | 耐熱性樹脂組成物、これを用いたプリプレグ及び積層板 |
JP2002265782A (ja) | 2001-03-14 | 2002-09-18 | Sumitomo Bakelite Co Ltd | 耐熱性樹脂組成物、これを用いたプリプレグ及び積層板 |
JP2005002226A (ja) | 2003-06-12 | 2005-01-06 | Kyocera Chemical Corp | 難燃性エポキシ樹脂組成物及びそれを用いた積層板関連製品 |
US20090311459A1 (en) * | 2006-11-14 | 2009-12-17 | Griswold Roy M | Laminate containing an adhesive-forming composition |
JP2015083649A (ja) | 2013-10-25 | 2015-04-30 | 東洋ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
JP2017115020A (ja) | 2015-12-24 | 2017-06-29 | 日立化成株式会社 | 熱硬化性樹脂組成物、プリプレグ、銅張積層板及びプリント配線板 |
JP2018165340A (ja) | 2017-03-28 | 2018-10-25 | 日立化成株式会社 | 熱硬化性樹脂組成物、プリプレグ、銅張積層板、プリント配線板及び半導体パッケージ |
JP6581746B1 (ja) | 2017-12-05 | 2019-09-25 | 株式会社クラレ | 変性液状ジエン系重合体 |
JP2019216308A (ja) | 2018-06-11 | 2019-12-19 | 三菱電機株式会社 | 地上デジタルテレビ放送受信装置、車載情報装置、及び、プログラム |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5814738A (ja) * | 1981-07-20 | 1983-01-27 | 松下電工株式会社 | 金属箔張り積層板の製法 |
JP2513599B2 (ja) * | 1985-02-27 | 1996-07-03 | 富士通株式会社 | 光導波路基板の製造方法 |
US7829116B2 (en) * | 2006-11-14 | 2010-11-09 | Momentive Performance Materials Inc. | Adhesive-forming composition and blend of adhesives obtained therefrom |
TWI449749B (zh) * | 2010-04-23 | 2014-08-21 | Panasonic Corp | 環氧樹脂組成物、預浸體、金屬被覆疊層板及印刷電路板 |
WO2012018126A1 (ja) * | 2010-08-06 | 2012-02-09 | 日立化成工業株式会社 | 相容化樹脂の製造法、熱硬化性樹脂組成物、プリプレグ及び積層板 |
CN107108820B (zh) * | 2015-02-19 | 2019-11-29 | 京瓷株式会社 | 树脂组合物、预浸渍体、覆金属箔层压板和布线基板 |
MY180265A (en) | 2015-05-13 | 2020-11-26 | Evonik Operations Gmbh | Improvement of the rolling resistance of diene-based rubber tyres by silane-modified polybutadiene |
DE102015210424A1 (de) * | 2015-06-08 | 2016-12-08 | Continental Reifen Deutschland Gmbh | Kautschukmischung und Fahrzeugreifen |
JP6787210B2 (ja) * | 2017-03-23 | 2020-11-18 | 味の素株式会社 | 樹脂組成物 |
-
2020
- 2020-11-25 KR KR1020227016805A patent/KR20220083802A/ko not_active Application Discontinuation
- 2020-11-25 CN CN202080081141.4A patent/CN114729064B/zh active Active
- 2020-11-25 EP EP20894047.8A patent/EP4067077A4/en active Pending
- 2020-11-25 WO PCT/JP2020/043816 patent/WO2021106931A1/ja unknown
- 2020-11-25 US US17/779,320 patent/US20230002532A1/en active Pending
- 2020-11-25 JP JP2021561453A patent/JP7307813B2/ja active Active
- 2020-11-26 TW TW109141548A patent/TWI829981B/zh active
Patent Citations (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61121699A (ja) * | 1984-11-19 | 1986-06-09 | Matsushita Electric Ind Co Ltd | 圧電スピ−カ |
JPS62198111A (ja) * | 1986-02-25 | 1987-09-01 | 東レ株式会社 | 金属蒸着フイルム及びコンデンサ− |
JPH06128547A (ja) | 1991-08-29 | 1994-05-10 | Hitachi Chem Co Ltd | 銅張積層板用銅箔接着剤 |
JPH06145380A (ja) | 1992-11-13 | 1994-05-24 | Nec Corp | プリプレグ及び銅張積層板 |
JP2000344949A (ja) | 1999-03-31 | 2000-12-12 | Nippon Mitsubishi Oil Corp | 自動車タイヤトレッド用ゴム組成物 |
JP2002226681A (ja) | 2001-02-02 | 2002-08-14 | Sumitomo Bakelite Co Ltd | 耐熱性樹脂組成物、これを用いたプリプレグ及び積層板 |
JP2002226680A (ja) | 2001-02-02 | 2002-08-14 | Sumitomo Bakelite Co Ltd | 耐熱性樹脂組成物、これを用いたプリプレグ及び積層板 |
JP2002265782A (ja) | 2001-03-14 | 2002-09-18 | Sumitomo Bakelite Co Ltd | 耐熱性樹脂組成物、これを用いたプリプレグ及び積層板 |
JP2005002226A (ja) | 2003-06-12 | 2005-01-06 | Kyocera Chemical Corp | 難燃性エポキシ樹脂組成物及びそれを用いた積層板関連製品 |
US20090311459A1 (en) * | 2006-11-14 | 2009-12-17 | Griswold Roy M | Laminate containing an adhesive-forming composition |
JP2015083649A (ja) | 2013-10-25 | 2015-04-30 | 東洋ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
JP2017115020A (ja) | 2015-12-24 | 2017-06-29 | 日立化成株式会社 | 熱硬化性樹脂組成物、プリプレグ、銅張積層板及びプリント配線板 |
JP2018165340A (ja) | 2017-03-28 | 2018-10-25 | 日立化成株式会社 | 熱硬化性樹脂組成物、プリプレグ、銅張積層板、プリント配線板及び半導体パッケージ |
JP6581746B1 (ja) | 2017-12-05 | 2019-09-25 | 株式会社クラレ | 変性液状ジエン系重合体 |
JP2019216308A (ja) | 2018-06-11 | 2019-12-19 | 三菱電機株式会社 | 地上デジタルテレビ放送受信装置、車載情報装置、及び、プログラム |
Non-Patent Citations (2)
Title |
---|
"Polymer Synthesis", vol. 1, 2010, KODANSHA LTD. |
See also references of EP4067077A4 |
Also Published As
Publication number | Publication date |
---|---|
EP4067077A4 (en) | 2024-01-03 |
EP4067077A1 (en) | 2022-10-05 |
CN114729064A (zh) | 2022-07-08 |
CN114729064B (zh) | 2023-09-29 |
JP7307813B2 (ja) | 2023-07-12 |
US20230002532A1 (en) | 2023-01-05 |
KR20220083802A (ko) | 2022-06-20 |
TW202126705A (zh) | 2021-07-16 |
TWI829981B (zh) | 2024-01-21 |
JPWO2021106931A1 (ja) | 2021-06-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TWI746758B (zh) | 樹脂組成物、預浸體、附樹脂之薄膜、附樹脂之金屬箔、覆金屬積層板及配線板 | |
CN108473758B (zh) | 聚苯醚树脂组合物、预浸渍体、覆金属层叠板及印刷布线板 | |
KR101710854B1 (ko) | N-치환 말레이미드기를 갖는 폴리페닐렌에테르 유도체, 및 그것을 사용한 열경화성 수지 조성물, 수지 바니시, 프리프레그, 금속 피복 적층판 및 다층 프린트 배선판 | |
JP4900313B2 (ja) | ポリフェニレンエーテル樹脂組成物、プリプレグ、積層板 | |
US11939443B2 (en) | Polyphenylene ether resin composition, prepreg, metal-clad laminate | |
WO2016038878A1 (ja) | 硬化性組成物、プリプレグ、樹脂付き金属箔、金属張積層板、及びプリント配線板 | |
WO2016009611A1 (ja) | 金属張積層板とその製造方法、樹脂付き金属箔、及びプリント配線板 | |
WO2007094359A1 (ja) | セミipn型複合体の熱硬化性樹脂組成物並びにこれを用いたワニス、プリプレグ及び金属張積層板 | |
WO2020096036A1 (ja) | 樹脂組成物、プリプレグ、積層板、樹脂フィルム、多層プリント配線板及びミリ波レーダー用多層プリント配線板 | |
JP2018095815A (ja) | 熱硬化性樹脂組成物、並びに、それを用いた樹脂ワニス、プリプレグ、樹脂付金属箔、樹脂フィルム、金属張積層板及びプリント配線板 | |
WO2019130735A1 (ja) | ポリフェニレンエーテル樹脂組成物、並びに、それを用いたプリプレグ、樹脂付きフィルム、樹脂付き金属箔、金属張積層板及び配線基板 | |
CN114174419B (zh) | 覆金属层叠板用树脂组合物、预浸料坯、及覆金属层叠板 | |
CN110709476A (zh) | 树脂组合物、布线板用绝缘层及层叠体 | |
JP7307813B2 (ja) | 末端変性ポリブタジエン、金属張積層板用樹脂組成物、プリプレグ、及び金属張積層板 | |
JPH06207096A (ja) | 低誘電率熱硬化性樹脂組成物 | |
JPH06192478A (ja) | 硬化性樹脂組成物並びにそれを用いたプリプレグ、積層板及び成形材料 | |
WO2021166649A1 (ja) | 硬化性樹脂組成物、プリプレグ、金属張積層板、及びプリント配線板 | |
JP2004059703A (ja) | エポキシ樹脂組成物、プリプレグ及び積層板 | |
WO2024111380A1 (ja) | 樹脂組成物、樹脂フィルム、プリプレグ、積層板、プリント配線板及び半導体パッケージ | |
WO2023145935A1 (ja) | 樹脂組成物、及びそれから得られる成形体、硬化物、フィルム、複合材料、硬化複合材料、積層体、樹脂付き金属箔、並びに回路基板材料用ワニス | |
KR20240038917A (ko) | 가요성 금속 클래드 라미네이트 및 그의 제조 방법 | |
JP2010037398A (ja) | プリプレグ及びそれを用いた積層体 | |
JPH04146911A (ja) | 硬化性樹脂組成物 | |
JP2010037400A (ja) | プリプレグ及びそれを用いた積層体 | |
JP2010037399A (ja) | プリプレグ及びそれを用いた積層体 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 20894047 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2021561453 Country of ref document: JP Kind code of ref document: A |
|
ENP | Entry into the national phase |
Ref document number: 20227016805 Country of ref document: KR Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
ENP | Entry into the national phase |
Ref document number: 2020894047 Country of ref document: EP Effective date: 20220629 |