KR100965018B1 - 열가소성 수지, 가교 수지 및 가교 수지 복합 재료의 제조방법 - Google Patents
열가소성 수지, 가교 수지 및 가교 수지 복합 재료의 제조방법 Download PDFInfo
- Publication number
- KR100965018B1 KR100965018B1 KR1020047021355A KR20047021355A KR100965018B1 KR 100965018 B1 KR100965018 B1 KR 100965018B1 KR 1020047021355 A KR1020047021355 A KR 1020047021355A KR 20047021355 A KR20047021355 A KR 20047021355A KR 100965018 B1 KR100965018 B1 KR 100965018B1
- Authority
- KR
- South Korea
- Prior art keywords
- thermoplastic resin
- group
- resin
- norbornene
- monomer
- 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.)
- Expired - Fee Related
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- 229920005992 thermoplastic resin Polymers 0.000 title claims abstract description 116
- 229920005989 resin Polymers 0.000 title claims abstract description 93
- 239000011347 resin Substances 0.000 title claims abstract description 93
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 62
- 239000000463 material Substances 0.000 title claims abstract description 59
- 239000000805 composite resin Substances 0.000 title claims abstract description 23
- -1 cyclic olefin Chemical class 0.000 claims abstract description 120
- 239000000178 monomer Substances 0.000 claims abstract description 105
- 239000000203 mixture Substances 0.000 claims abstract description 75
- 238000000034 method Methods 0.000 claims abstract description 67
- 238000005649 metathesis reaction Methods 0.000 claims abstract description 53
- 239000007788 liquid Substances 0.000 claims abstract description 49
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 36
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims abstract description 30
- 239000012986 chain transfer agent Substances 0.000 claims abstract description 28
- 239000002685 polymerization catalyst Substances 0.000 claims abstract description 25
- 238000007142 ring opening reaction Methods 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims description 74
- 238000004132 cross linking Methods 0.000 claims description 60
- 238000006116 polymerization reaction Methods 0.000 claims description 47
- 229910052751 metal Inorganic materials 0.000 claims description 31
- 239000002184 metal Substances 0.000 claims description 31
- 239000004593 Epoxy Substances 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 238000012662 bulk polymerization Methods 0.000 claims description 24
- 239000011888 foil Substances 0.000 claims description 23
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 239000002657 fibrous material Substances 0.000 claims description 12
- 125000004018 acid anhydride group Chemical group 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 11
- 238000010030 laminating Methods 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 125000003700 epoxy group Chemical group 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000007822 coupling agent Substances 0.000 claims description 5
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 238000003860 storage Methods 0.000 abstract description 16
- 238000010292 electrical insulation Methods 0.000 abstract description 6
- 229920001169 thermoplastic Polymers 0.000 abstract description 4
- 239000004416 thermosoftening plastic Substances 0.000 abstract description 4
- 238000010924 continuous production Methods 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 58
- 239000011889 copper foil Substances 0.000 description 51
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 26
- 150000003254 radicals Chemical class 0.000 description 25
- 239000000243 solution Substances 0.000 description 21
- 238000010438 heat treatment Methods 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 17
- 239000002585 base Substances 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 16
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 15
- 239000011521 glass Substances 0.000 description 14
- 239000003365 glass fiber Substances 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 229910052782 aluminium Inorganic materials 0.000 description 11
- 125000004429 atom Chemical group 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 10
- 125000005842 heteroatom Chemical group 0.000 description 10
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 10
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 10
- 239000004810 polytetrafluoroethylene Substances 0.000 description 10
- 229910052707 ruthenium Inorganic materials 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000004817 gas chromatography Methods 0.000 description 8
- 239000004698 Polyethylene Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 7
- 229910052802 copper Inorganic materials 0.000 description 7
- 239000010949 copper Substances 0.000 description 7
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 7
- PHCKFVVLVZFFLU-UHFFFAOYSA-N dodec-4-ene Chemical compound CCCCCCCC=CCCC PHCKFVVLVZFFLU-UHFFFAOYSA-N 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 239000003063 flame retardant Substances 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 229910052742 iron Inorganic materials 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 238000000465 moulding Methods 0.000 description 7
- 229920000573 polyethylene Polymers 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 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 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 238000005452 bending Methods 0.000 description 5
- LURVUWBWEGPODG-UHFFFAOYSA-L dichlororuthenium;tricyclohexylphosphane Chemical compound [Cl-].[Cl-].[Ru+2].C1CCCCC1P(C1CCCCC1)C1CCCCC1 LURVUWBWEGPODG-UHFFFAOYSA-L 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 239000012778 molding material Substances 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 150000001451 organic peroxides Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 150000003573 thiols Chemical class 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000001925 cycloalkenes Chemical class 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
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- 229930195733 hydrocarbon Natural products 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000007493 shaping process Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- OJOWICOBYCXEKR-APPZFPTMSA-N (1S,4R)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound CC=C1C[C@@H]2C[C@@H]1C=C2 OJOWICOBYCXEKR-APPZFPTMSA-N 0.000 description 3
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 3
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 3
- XUFPYLQWLKKGDQ-UHFFFAOYSA-N 4,4a,9,9a-tetrahydro-1,4-methano-1h-fluorene Chemical compound C12CC3=CC=CC=C3C1C1C=CC2C1 XUFPYLQWLKKGDQ-UHFFFAOYSA-N 0.000 description 3
- KNDQHSIWLOJIGP-UHFFFAOYSA-N 826-62-0 Chemical compound C1C2C3C(=O)OC(=O)C3C1C=C2 KNDQHSIWLOJIGP-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000012327 Ruthenium complex Substances 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
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- 230000001070 adhesive effect Effects 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- FYGUSUBEMUKACF-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carboxylic acid Chemical compound C1C2C(C(=O)O)CC1C=C2 FYGUSUBEMUKACF-UHFFFAOYSA-N 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
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- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 3
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- 238000002360 preparation method Methods 0.000 description 3
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- 238000007151 ring opening polymerisation reaction Methods 0.000 description 3
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- 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
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical group C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 2
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- XCGKRTHKVBCXLN-UHFFFAOYSA-N 3a,4,4a,5,8,8a,9,9a-octahydro-4,9:5,8-dimethano-1h-benz(f)indene Chemical compound C1C2C3C(C=C4)CC4C3C1C1C2C=CC1 XCGKRTHKVBCXLN-UHFFFAOYSA-N 0.000 description 2
- LKVFCSWBKOVHAH-UHFFFAOYSA-N 4-Ethoxyphenol Chemical compound CCOC1=CC=C(O)C=C1 LKVFCSWBKOVHAH-UHFFFAOYSA-N 0.000 description 2
- INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-UHFFFAOYSA-N 0.000 description 2
- CJQNJRMLJAAXOS-UHFFFAOYSA-N 5-prop-1-enylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=CC)CC1C=C2 CJQNJRMLJAAXOS-UHFFFAOYSA-N 0.000 description 2
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
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- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- WMVSVUVZSYRWIY-UHFFFAOYSA-N [(4-benzoyloxyiminocyclohexa-2,5-dien-1-ylidene)amino] benzoate Chemical class C=1C=CC=CC=1C(=O)ON=C(C=C1)C=CC1=NOC(=O)C1=CC=CC=C1 WMVSVUVZSYRWIY-UHFFFAOYSA-N 0.000 description 2
- CEFJHONIESABKA-UHFFFAOYSA-L [Ru](Cl)Cl.C1(=CC=CC=C1)CC=C1C(CCCC1)P(C1CCCCC1)C1CCCCC1 Chemical compound [Ru](Cl)Cl.C1(=CC=CC=C1)CC=C1C(CCCC1)P(C1CCCCC1)C1CCCCC1 CEFJHONIESABKA-UHFFFAOYSA-L 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 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
- 150000004054 benzoquinones Chemical class 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
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- HKFSBKQQYCMCKO-UHFFFAOYSA-N trichloro(prop-2-enyl)silane Chemical compound Cl[Si](Cl)(Cl)CC=C HKFSBKQQYCMCKO-UHFFFAOYSA-N 0.000 description 1
- YHVKBMGCQCHIMZ-VOTSOKGWSA-N trichloro-[(e)-2-phenylethenyl]silane Chemical compound Cl[Si](Cl)(Cl)\C=C\C1=CC=CC=C1 YHVKBMGCQCHIMZ-VOTSOKGWSA-N 0.000 description 1
- XFCTVRBFLKBUFQ-UHFFFAOYSA-N trideca-2,8-diene Chemical compound CCCCC=CCCCCC=CC XFCTVRBFLKBUFQ-UHFFFAOYSA-N 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- KXANWKNLLBYXLM-UHFFFAOYSA-N trimethoxy(4-tetracyclo[6.2.1.13,6.02,7]dodec-9-enyl)silane Chemical compound C1C(C23)C=CC1C3C1CC2CC1[Si](OC)(OC)OC KXANWKNLLBYXLM-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- SUDSHRFJYWYREN-UHFFFAOYSA-N tris(ethenyl)-prop-2-enylsilane Chemical compound C=CC[Si](C=C)(C=C)C=C SUDSHRFJYWYREN-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C39/00—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor
- B29C39/02—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor for making articles of definite length, i.e. discrete articles
- B29C39/10—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor for making articles of definite length, i.e. discrete articles incorporating preformed parts or layers, e.g. casting around inserts or for coating articles
-
- 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
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/02—Polymerisation in bulk
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/08—Epoxidation
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/50—Partial depolymerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
-
- 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
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Laminated Bodies (AREA)
Abstract
Description
Claims (20)
- 하기 (I) 내지 (III)의 성분을 포함하는 중합성 조성물(A)을 괴상 중합하는 것을 특징으로 하는 후가교가능한 열가소성 수지의 제조 방법.(I) 분자내에 복분해 개환 반응 부위를 2개 이상 갖는 환상 올레핀(α)을 전 단량체량에 대하여 10중량% 이상 함유하여 이루어지는 단량체액, 또는 노보넨계 단량체 및 가교제를 함유하여 이루어지는 단량체액(II) 복분해 중합촉매(III) 연쇄이동제
- 분자내에 복분해 개환 반응 부위를 2개 이상 갖는 환상 올레핀(α)을 전 단량체량에 대하여 10중량% 이상 함유하여 이루어지는 단량체액, 복분해 중합 촉매 및 연쇄이동제를 포함하는 중합성 조성물(A)을 괴상 중합하는 것을 특징으로 하는 후가교가능한 열가소성 수지의 제조 방법.
- 노보넨계 단량체, 복분해 중합촉매, 연쇄이동제 및 가교제를 포함하는 중합성 조성물(A)을 괴상 중합하는 것을 특징으로 하는 후가교가능한 열가소성 수지의 제조 방법.
- 제 1 항 내지 제 3 항 중 어느 한 항에 있어서,괴상 중합의 중합시 최고 온도가 230℃ 미만인 것을 특징으로 하는 후가교가능한 열가소성 수지의 제조 방법.
- 제 1 항 내지 제 3 항 중 어느 한 항에 있어서,중합 반응률이 80% 이상인 것을 특징으로 하는 후가교가능한 열가소성 수지의 제조 방법.
- 제 1 항 내지 제 3 항 중 어느 한 항에 있어서,상기 연쇄이동제로서, 식 CH2=CH-Q(식중, Q은 메타크릴로일기, 아크릴로일기, 비닐실릴기, 에폭시기 및 아미노기로부터 선택되는 기를 적어도 하나 갖는 기를 나타낸다)로 표시되는 화합물을 이용하는 것을 특징으로 하는 후가교가능한 열가소성 수지의 제조 방법.
- 제 1 항 또는 제 2 항에 있어서,상기 환상 올레핀(α)으로서 다이사이클로펜타다이엔을 이용하는 것을 특징으로 하는 후가교가능한 열가소성 수지의 제조 방법.
- 제 1 항 또는 제 3 항에 있어서,상기 노보넨계 단량체로서, 카복실기 또는 산무수물기를 갖는 노보넨계 단량체를 포함하는 노보넨계 단량체 혼합물을 이용하고, 상기 가교제로서 에폭시 화합물을 이용하는 것을 특징으로 하는 후가교가능한 열가소성 수지의 제조 방법.
- 제 1 항 또는 제 3 항에 있어서,상기 가교제로서 라디칼 발생제를 이용하고, 상기 라디칼 발생제의 1분간 반감기 온도 이하의 반응 온도에서 중합성 조성물(A)을 괴상 중합하는 것을 특징으로 하는 후가교가능한 열가소성 수지의 제조 방법.
- 제 9 항에 있어서,상기 중합성 조성물(A)로서, 추가로 라디칼 가교지연제를 포함하는 것을 이용하는 것을 특징으로 하는 후가교가능한 열가소성 수지의 제조 방법.
- 삭제
- 제 1 항 내지 제 3 항 중 어느 한 항에 있어서,상기 중합성 조성물(A)을 지지체상에서 괴상 중합함으로써 필름 형상으로 성형하는 것을 특징으로 하는 후가교가능한 열가소성 수지의 제조 방법.
- 제 12 항에 있어서,상기 지지체로서, 금속박 또는 수지 필름을 이용하는 것을 특징으로 하는 후가교가능한 열가소성 수지의 제조 방법.
- 제 1 항 내지 제 3 항 중 어느 한 항에 있어서,상기 중합성 조성물(A)을 형내에서 괴상 중합함으로써 소정의 형상으로 성형하는 것을 특징으로 하는 후가교가능한 열가소성 수지의 제조 방법.
- 제 1 항 내지 제 3 항 중 어느 한 항에 있어서,상기 중합성 조성물(A)을 섬유 재료에 함침시킨 후, 괴상 중합하는 것을 특징으로 하는 후가교가능한 열가소성 수지의 제조 방법.
- 제 1 항 내지 제 3 항 중 어느 한 항에 따른 제조 방법에 의해 얻어지는 후가교가능한 열가소성 수지를 가교하는 공정을 갖는 가교 수지의 제조 방법.
- 제 1 항 내지 제 3 항 중 어느 한 항에 따른 제조 방법에 의해 얻어지는 후가교가능한 열가소성 수지를 기재와 적층하고, 열가소성 수지 부분을 가교하는 공정을 갖는 가교 수지 복합 재료의 제조 방법.
- 제 17 항에 있어서,상기 기재로서 금속박을 이용하는 것을 특징으로 하는 가교 수지 복합 재료의 제조 방법.
- 제 18 항에 있어서,상기 금속박으로서, 하기 화학식 1로 표시되는 실레인 커플링제, 또는 하기 화학식 2로 표시되는 티올계 커플링제로 처리된 것을 이용하는 가교 수지 복합 재료의 제조 방법.화학식 1RSiXYZ화학식 2T(SH)n(식중, R은 말단에 이중결합, 머캅토기 또는 아미노기를 갖는 기를 나타내고, X 및 Y는 각각 독립적으로 가수분해성기, 수산기 또는 알킬기를 나타내고, Z는 가수분해성기 또는 수산기를 나타낸다. T는 방향환, 지방족환, 복소환 또는 지방족쇄를 나타내고, n은 2 이상의 정수를 나타낸다. )
- 제 17 항에 있어서,상기 기재로서 프린트 배선판을 이용하는 가교 수지 복합 재료의 제조 방법.
Applications Claiming Priority (5)
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JP2002190929A JP2004035615A (ja) | 2002-06-28 | 2002-06-28 | 熱可塑性樹脂、架橋樹脂、架橋複合材料および銅張り積層板の製造方法 |
JPJP-P-2002-00190929 | 2002-06-28 | ||
JPJP-P-2002-00219255 | 2002-07-29 | ||
JPJP-P-2003-00010967 | 2003-01-20 | ||
PCT/JP2003/008105 WO2004003052A1 (ja) | 2002-06-28 | 2003-06-26 | 熱可塑性樹脂、架橋樹脂及び架橋樹脂複合材料の製造方法 |
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Citations (3)
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JP2001026059A (ja) | 1999-05-10 | 2001-01-30 | Sekisui Chem Co Ltd | ノルボルネン系ポリマー連続成形体の製造方法 |
JP2001278963A (ja) | 2000-03-31 | 2001-10-10 | Nippon Zeon Co Ltd | 硬化可能な成形材、成形品およびそれらの製造方法 |
JP2002137233A (ja) | 2000-11-02 | 2002-05-14 | Hitachi Chem Co Ltd | メタセシス重合体の注入成形方法及び注入成形装置 |
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JP2001026059A (ja) | 1999-05-10 | 2001-01-30 | Sekisui Chem Co Ltd | ノルボルネン系ポリマー連続成形体の製造方法 |
JP2001278963A (ja) | 2000-03-31 | 2001-10-10 | Nippon Zeon Co Ltd | 硬化可能な成形材、成形品およびそれらの製造方法 |
JP2002137233A (ja) | 2000-11-02 | 2002-05-14 | Hitachi Chem Co Ltd | メタセシス重合体の注入成形方法及び注入成形装置 |
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