JPWO2014125921A1 - 樹脂組成物及びその成形体 - Google Patents
樹脂組成物及びその成形体 Download PDFInfo
- Publication number
- JPWO2014125921A1 JPWO2014125921A1 JP2015500175A JP2015500175A JPWO2014125921A1 JP WO2014125921 A1 JPWO2014125921 A1 JP WO2014125921A1 JP 2015500175 A JP2015500175 A JP 2015500175A JP 2015500175 A JP2015500175 A JP 2015500175A JP WO2014125921 A1 JPWO2014125921 A1 JP WO2014125921A1
- Authority
- JP
- Japan
- Prior art keywords
- group
- cyclic olefin
- hydrogenated product
- ring
- olefin ring
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000011342 resin composition Substances 0.000 title claims abstract description 45
- -1 cyclic olefin Chemical group 0.000 claims abstract description 163
- 229920000642 polymer Polymers 0.000 claims abstract description 147
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 114
- 238000007142 ring opening reaction Methods 0.000 claims abstract description 102
- 239000000178 monomer Substances 0.000 claims abstract description 57
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims abstract description 40
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 31
- 229920005989 resin Polymers 0.000 claims abstract description 24
- 239000011347 resin Substances 0.000 claims abstract description 24
- 239000003365 glass fiber Substances 0.000 claims abstract description 23
- 238000000465 moulding Methods 0.000 claims abstract description 17
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 14
- 229920001296 polysiloxane Chemical class 0.000 claims description 7
- 239000000047 product Substances 0.000 description 99
- 150000002736 metal compounds Chemical class 0.000 description 46
- 125000001424 substituent group Chemical group 0.000 description 39
- 238000005984 hydrogenation reaction Methods 0.000 description 33
- 238000000034 method Methods 0.000 description 18
- 238000006116 polymerization reaction Methods 0.000 description 16
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 16
- 125000000217 alkyl group Chemical group 0.000 description 15
- 239000000835 fiber Substances 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 230000004048 modification Effects 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 13
- 238000012986 modification Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000005452 bending Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 125000005843 halogen group Chemical group 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 239000002685 polymerization catalyst Substances 0.000 description 11
- 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 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 150000002430 hydrocarbons Chemical group 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 239000003638 chemical reducing agent Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 230000006872 improvement Effects 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000008188 pellet Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 6
- 125000002524 organometallic group Chemical group 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000003607 modifier Substances 0.000 description 5
- 230000000737 periodic effect Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 4
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 125000005103 alkyl silyl group Chemical group 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229920006038 crystalline resin Polymers 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000001746 injection moulding Methods 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 150000001451 organic peroxides Chemical class 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- XBFJAVXCNXDMBH-UHFFFAOYSA-N tetracyclo[6.2.1.1(3,6).0(2,7)]dodec-4-ene Chemical compound C1C(C23)C=CC1C3C1CC2CC1 XBFJAVXCNXDMBH-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 4
- 229910052721 tungsten Inorganic materials 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- NOSXUFXBUISMPR-UHFFFAOYSA-N 1-tert-butylperoxyhexane Chemical compound CCCCCCOOC(C)(C)C NOSXUFXBUISMPR-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 230000037048 polymerization activity Effects 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000003014 reinforcing effect Effects 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 150000003624 transition metals Chemical group 0.000 description 3
- 239000010937 tungsten Substances 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- LTQBNYCMVZQRSD-UHFFFAOYSA-N (4-ethenylphenyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=C(C=C)C=C1 LTQBNYCMVZQRSD-UHFFFAOYSA-N 0.000 description 2
- MEBONNVPKOBPEA-UHFFFAOYSA-N 1,1,2-trimethylcyclohexane Chemical compound CC1CCCCC1(C)C MEBONNVPKOBPEA-UHFFFAOYSA-N 0.000 description 2
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
- 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
- YAQDPWONDFRAHF-UHFFFAOYSA-N 2-methyl-2-(2-methylpentan-2-ylperoxy)pentane Chemical compound CCCC(C)(C)OOC(C)(C)CCC YAQDPWONDFRAHF-UHFFFAOYSA-N 0.000 description 2
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000005370 alkoxysilyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- NIDNOXCRFUCAKQ-UHFFFAOYSA-N bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1C2C=CC1C(C(=O)O)C2C(O)=O NIDNOXCRFUCAKQ-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 238000000748 compression moulding Methods 0.000 description 2
- 150000001925 cycloalkenes Chemical group 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 2
- MBGQQKKTDDNCSG-UHFFFAOYSA-N ethenyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(C=C)OCC MBGQQKKTDDNCSG-UHFFFAOYSA-N 0.000 description 2
- ZLNAFSPCNATQPQ-UHFFFAOYSA-N ethenyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C=C ZLNAFSPCNATQPQ-UHFFFAOYSA-N 0.000 description 2
- GCPCLEKQVMKXJM-UHFFFAOYSA-N ethoxy(diethyl)alumane Chemical compound CCO[Al](CC)CC GCPCLEKQVMKXJM-UHFFFAOYSA-N 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000010559 graft polymerization reaction Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
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- 229910052725 zinc Inorganic materials 0.000 description 1
- QMBQEXOLIRBNPN-UHFFFAOYSA-L zirconocene dichloride Chemical compound [Cl-].[Cl-].[Zr+4].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 QMBQEXOLIRBNPN-UHFFFAOYSA-L 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
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Abstract
Description
また、本発明によれば、樹脂成形体が電子部品である前記の樹脂成形体が提供される。
電子部品は、アンテナやコネクタなどの電子部品に好適に用いられる。
1)樹脂組成物
本発明の樹脂組成物は、樹脂成分として、結晶性環状オレフィン開環重合体水素添加物0〜99重量%、好ましくは0〜95重量%と、変性結晶性環状オレフィン開環重合体水素添加物1〜100重量%、好ましくは5〜100重量%とを含有する。機械強度の最大値は、変性結晶性環状オレフィン開環重合体水素添加物の割合が、3〜20重量部の間にあり、変性結晶性環状オレフィン開環重合体水素添加物の割合が多すぎると、緩やかに機械特性が低下する傾向にあるが、変性結晶性環状オレフィン開環重合体水素添加物が100重量%であっても、変性結晶性環状オレフィン開環重合体水素添加物を配合しない場合(即ち結晶性環状オレフィン開環重合体水素添加物が100重量%)より、2割程度以上高い機械特性が得られる。
本発明に用いる結晶性環状オレフィン開環重合体水素添加物は、3環以上の環を有する多環式ノルボルネン系単量体(以下、単に「多環式ノルボルネン系単量体」ということがある)を少なくとも含有する単量体を開環重合し、得られた開環重合体の主鎖二重結合を水素化することにより得られるものであって、かつ、結晶性を有するものである。
金属化合物(3)は、金属イミド結合を含んでなるものである。R8は、金属イミド結合を構成する窒素原子上の置換基である。
用いる有機溶媒は、目的とする開環重合体やその水素添加物が所定の条件で溶解もしくは分散させることが可能であり、重合反応や水素化反応を阻害しないものであれば、特に限定されない。
また、以上のようにして得られる結晶性環状オレフィン開環重合体水素添加物では、水素化反応に供した開環重合体が有するシンジオタクチック立体規則性が維持される。したがって、得られる結晶性環状オレフィン開環重合体水素添加物は、シンジオタクチック立体規則性を有する。本発明に用いる結晶性環状オレフィン開環重合体水素添加物におけるラセモ・ダイアッドの割合は、その水素添加物が結晶性を有する限りにおいて特に限定されないが、通常55%以上、好ましくは60%以上、より好ましくは65〜99%である。
本発明に用いる変性結晶性環状オレフィン開環重合体水素添加物は、上述の結晶性環状オレフィン開環重合体水素添加物を不飽和カルボン酸又はシリコーン誘導体でグラフト変性して得られるものである。
尚、ここでグラフト変性率は、FT−IRスペクトルから算出されるものである。
本発明の樹脂組成物に配合するガラス繊維の形態としては、例えば、チョップドストランド、カットファイバー、ミルドファイバー、フィラメント、クロス、ステープルヤーンなどと称されるものが適用できる。
本発明の樹脂組成物に配合可能なその他の成分としては、フェノール系酸化防止剤、リン系酸化防止剤、イオウ系酸化防止剤などの酸化防止剤;ヒンダードアミン系光安定剤などの光安定剤;石油系ワックスやフィッシャートロプシュワックスやポリアルキレンワックスなどのワックス;ソルビトール系化合物、有機リン酸の金属塩、有機カルボン酸の金属塩、カオリン及びタルクなどの核剤;ジアミノスチルベン誘導体、クマリン誘導体、アゾール系誘導体(例えば、ベンゾオキサゾール誘導体、ベンゾトリアゾール誘導体、ベンゾイミダゾール誘導体、及びベンゾチアソール誘導体)、カルバゾール誘導体、ピリジン誘導体、ナフタル酸誘導体、及びイミダゾロン誘導体などの蛍光増白剤;ベンゾフェノン系紫外線吸収剤、サリチル酸系紫外線吸収剤、ベンゾトリアゾール系紫外線吸収剤などの紫外線吸収剤;タルク、シリカ、炭酸カルシウムなどの無機充填材;着色剤;難燃剤;難燃助剤;帯電防止剤;可塑剤;近赤外線吸収剤;滑剤、及び、軟質重合体などの結晶性環状オレフィン開環重合体水素添加物以外の高分子材料;等を例示することができる。
本発明の樹脂成形体を得る方法に格別な制限は無く、公知の成形法を用いることができる。例えば、射出成形、押出成形、プレス成形、インフレーション成形、ブロー成形、カレンダー成形、注型成形、圧縮成形、延伸成形等の方法が挙げられる。成形法は目的とする形状等に応じて選択すればよいが、本発明の樹脂組成物は優れた成形性(溶融成形性)を有することから、量産性に優れる射出成形法を適用することが好ましい。
また、各例における測定や評価は、以下の方法により行った。
ゲル・パーミエーション・クロマトグラフィー(GPC)システム HLC−8220(東ソー社製)で、Hタイプカラム(東ソー社製)を用い、テトラヒドロフランを溶媒として40℃で測定し、ポリスチレン換算値として求めた。
1H−NMR測定により求めた。
(3)結晶性環状オレフィン開環重合体水素添加物の融点
示差走査熱量計を用いて、昇温温度:10℃/分で測定した。
オルトジクロロベンゼン−d4を溶媒として、150℃で13C−NMR測定を行い、メソ・ダイアッド由来の43.35ppmのシグナルと、ラセモ・ダイアッド由来の43.43ppmのシグナルの強度比に基づいて決定した。
変性結晶性環状オレフィン開環重合体水素添加物中の極性基の存在の確認は、FT−IRにより透過法で行うことができる。例えば無水マレイン酸を導入した場合は、FT−IRスペクトルで1790cm−1にC=O基に基づく吸収帯が観察され、ビニルトリメトキシシランを導入した場合は、FT−IRスペクトルで825及び739cm−1にSi−OCH3基に基づく吸収帯が観察される。また、結晶性環状オレフィン開環重合体水素添加物に対する極性基の導入量もFT−IRにより定量可能である。導入量は、それぞれの極性基に基づく吸収帯のピーク高さと、結晶性環状オレフィン開環重合体水素添加物に基づく920cm−1の吸収帯のピーク高さの比を算出し、あらかじめ作成した検量線を用いて算出した。
オーブンを用いた260℃×10秒間の熱処理を3回行った後、試験片を目視観察することにより耐リフロー性を評価した。ここで、試験片が熱処理の前後で変形、溶融することなく形状を保持していたものを○、変形、溶融が見られたものを×とした。
ネットワークアナライザ(製品名「N5230A」、アジレント社製)を用いて、円筒空洞共振器法によりASTM D2520に準じて、誘電率及び誘電正接を測定した。測定時の周波数は、1GHzとした。
オートグラフ(製品名「AGS−5kNJ・TCR2」、島津製作所社製)を用いてJIS K 7171に準じて試験速度2mm/minで曲げ試験を行い、曲げ強度を測定した。
〔結晶性環状オレフィン開環重合体水素添加物の合成〕
充分に乾燥した後、窒素置換したガラス製耐圧反応容器に、ジシクロペンタジエン(エンド体含有率99%以上)の75%シクロヘキサン溶液40部(ジシクロペンタジエンの量として30部)を仕込み、さらに、シクロヘキサン738部及び1−ヘキセン2.0部を加え、50℃に加温した。一方、テトラクロロタングステンフェニルイミド(テトラヒドロフラン)錯体1.1部を56部のトルエンに溶解した溶液に、19重量%のジエチルアルミニウムエトキシド/n−ヘキサン溶液4.6部を加えて10分間攪拌し、触媒溶液を調製した。この触媒溶液を反応器に加えて開環重合反応を開始させた。その後、50℃を保ちながら、5分毎に75%ジシクロペンタジエン/シクロヘキサン溶液40部を9回添加した後、2時間反応を継続した。ついで、少量のイソプロパノールを加えて、重合反応を停止させた後、重合反応溶液を多量のイソプロパノール中に注ぎ、開環重合体を凝固させた。
上記で得られた結晶性環状オレフィン開環重合体水素添加物のペレット100部に対して無水マレイン酸(製品名「CRYSTAL MAN(登録商標)」、日油社製)2.0部及び2,5−ジメチル−2,5−ジ(t−ブチルパーオキシ)ヘキサン(製品名「パーヘキサ(登録商標) 25B」、日油社製)0.2部を添加した。この混合物を、二軸押出機(製品名「TEM35B」、東芝機械社製)を用いて、樹脂温度270℃、スクリュー回転数100rpm、滞留時間60〜70秒で混練し、ストランド状に押出し、水冷した後、ペレタイザーによりカッティングし、無水マレイン酸が導入された変性結晶性環状オレフィン開環重合体水素添加物A(表1では、「変性重合体A」という)のペレット97部を得た。
上記で得られた結晶性環状オレフィン開環重合体水素添加物のペレット100部に対してビニルトリメトキシシラン2.0部及び2,5−ジメチル−2,5−ジ(t−ブチルパーオキシ)ヘキサン(製品名「パーヘキサ(登録商標) 25B」、日油社製)0.2部を添加した。この混合物を、二軸押出機(製品名「TEM35B」、東芝機械社製)を用いて、樹脂温度270℃、スクリュー回転数100rpm、滞留時間60〜70秒で混練し、ストランド状に押出し、空冷した後、ペレタイザーによりカッティングし、アルコキシシリル基が導入された変性結晶性環状オレフィン開環重合体水素添加物B(表1では、「変性重合体B」という)のペレット97部を得た。
結晶性環状オレフィン開環重合体水素添加物97部、変性結晶性環状オレフィン開環重合体水素添加物A3部、ガラス繊維(商品名「CS 3PE−960」、繊維長3mm、繊維径13μm、日東紡社製)100部、酸化防止剤(テトラキス〔メチレン−3−(3’,5’−ジ−tert−ブチル−4’−ヒドロキシフェニル)プロピオネート〕メタン、商品名「イルガノックス(登録商標)1010」、BASFジャパン社製)0.8部を混合後、二軸押出機(製品名「TEM35B」、東芝機械社製)を用い、樹脂温度270℃、滞留時間30秒の条件で混練し、ストランド上に押出し、水冷した後、ペレタイザーによりカッティングし、得られた混練物をペレット化した。その後、竪型射出成形機(製品名「SAV−30−30−P」、三城精機社製)で成形温度290℃、金型温度150℃の条件で各々の試験に用いる試験片を成形した。耐リフロー試験には、縦70mm、横30mm、厚さ1.0mmの平板を用いた。誘電正接の測定には、耐リフロー試験片を縦方向に幅1.0mmに切削したものを用いた。また、曲げ試験には、JIS K 7171に規定する曲げ試験片を用いた。組成物の組成とそれぞれの評価結果を、表1にまとめて示す。
実施例1において、組成物の配合量(重量部)を表1に示す通りに変更したこと以外は、実施例1と同様にして、成形体を得て、その評価を行った。それぞれの評価結果は、表1にまとめて示した。なお、表1において、ガラスビーズは粒径約45μmのホウ珪酸ガラス(製品名「ユニビーズ(登録商標)UB−02E」、ユニチカ社製)である。
Claims (5)
- 3環以上の環を有する多環式ノルボルネン系単量体由来の繰返し単位を有し、極性基を有しない結晶性環状オレフィン開環重合体水素添加物0〜99重量%と、3環以上の環を有する多環式ノルボルネン系単量体由来の繰返し単位を有し、極性基を有する変性結晶性環状オレフィン開環重合体水素添加物1〜100重量%とからなる樹脂成分100重量部に対して、5〜150重量部のガラス繊維を含有する樹脂組成物。
- 3環以上の環を有する多環式ノルボルネン系単量体由来の繰返し単位を有し、極性基を有する変性結晶性環状オレフィン開環重合体水素添加物が、3環以上の環を有する多環式ノルボルネン系単量体由来の繰返し単位を有し、極性基を有しない結晶性環状オレフィン開環重合体水素添加物を、不飽和カルボン酸又はシリコーン誘導体によりグラフト変性して得られるものである請求項1記載の樹脂組成物。
- 3環以上の環を有する多環式ノルボルネン系単量体由来の繰返し単位を有し、極性基を有しない結晶性環状オレフィン開環重合体水素添加物が、シンジオタクチック立体規則性を有する請求項1または2記載の樹脂組成物。
- 請求項1乃至3のいずれか1項に記載の樹脂組成物を成形して得られる樹脂成形体。
- 樹脂成形体が電子部品である請求項4記載の樹脂成形体。
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EP3085722A4 (en) * | 2013-12-20 | 2017-08-16 | Zeon Corporation | Resin material and resin film |
KR102656214B1 (ko) * | 2014-10-28 | 2024-04-08 | 니폰 제온 가부시키가이샤 | 수지 필름, 배리어 필름 및 도전성 필름, 그리고, 이들의 제조 방법 |
JP7120764B2 (ja) * | 2015-03-09 | 2022-08-17 | 日本ゼオン株式会社 | シンジオタクチック-ノルボルネン系開環重合体水素化物 |
KR20220122601A (ko) * | 2019-12-25 | 2022-09-02 | 니폰 제온 가부시키가이샤 | 수지 조성물 및 이것을 성형하여 이루어지는 성형물, 그리고, 수지 조성물의 제조 방법 |
KR102563213B1 (ko) * | 2020-11-20 | 2023-08-04 | 코오롱인더스트리 주식회사 | 수지 조성물, 이의 제조방법, 상기 수지 조성물을 포함하는 고무 조성물, 이를 포함하는 가스 배리어 필름, 및 상기 가스 배리어 필름을 포함한 타이어 |
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2014
- 2014-01-29 JP JP2015500175A patent/JP6304227B2/ja active Active
- 2014-01-29 US US14/767,535 patent/US9631083B2/en active Active
- 2014-01-29 TW TW103103451A patent/TW201434954A/zh unknown
- 2014-01-29 WO PCT/JP2014/051933 patent/WO2014125921A1/ja active Application Filing
- 2014-01-29 EP EP14751138.0A patent/EP2957596A4/en not_active Withdrawn
- 2014-01-29 KR KR1020157021633A patent/KR102110151B1/ko active IP Right Grant
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WO2001014446A1 (fr) * | 1999-08-25 | 2001-03-01 | Zeon Corporation | Polymeres de norbornene par ouverture de cycle, produits de leur hydrogenation et procedes de productions de ces deux types de polymeres |
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JP2013256596A (ja) * | 2012-06-13 | 2013-12-26 | Nippon Zeon Co Ltd | 樹脂組成物及びその成形品 |
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CN104955894A (zh) | 2015-09-30 |
TW201434954A (zh) | 2014-09-16 |
US9631083B2 (en) | 2017-04-25 |
US20160032094A1 (en) | 2016-02-04 |
EP2957596A4 (en) | 2016-08-31 |
JP6304227B2 (ja) | 2018-04-04 |
WO2014125921A1 (ja) | 2014-08-21 |
KR102110151B1 (ko) | 2020-05-13 |
EP2957596A1 (en) | 2015-12-23 |
KR20150117265A (ko) | 2015-10-19 |
CN104955894B (zh) | 2016-12-28 |
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