JP5528553B2 - ポリジシクロペンタジエンおよびそれに基づく材料を製造する方法 - Google Patents
ポリジシクロペンタジエンおよびそれに基づく材料を製造する方法 Download PDFInfo
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- JP5528553B2 JP5528553B2 JP2012519495A JP2012519495A JP5528553B2 JP 5528553 B2 JP5528553 B2 JP 5528553B2 JP 2012519495 A JP2012519495 A JP 2012519495A JP 2012519495 A JP2012519495 A JP 2012519495A JP 5528553 B2 JP5528553 B2 JP 5528553B2
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- dicyclopentadiene
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- 229920001153 Polydicyclopentadiene Polymers 0.000 title claims description 65
- 238000000034 method Methods 0.000 title claims description 32
- 230000008569 process Effects 0.000 title claims description 11
- 239000000463 material Substances 0.000 title description 16
- 239000003054 catalyst Substances 0.000 claims description 79
- 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 72
- 239000000654 additive Substances 0.000 claims description 30
- 238000006116 polymerization reaction Methods 0.000 claims description 28
- 230000000996 additive effect Effects 0.000 claims description 23
- 239000011541 reaction mixture Substances 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 150000001925 cycloalkenes Chemical class 0.000 claims description 10
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 10
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 8
- 239000002861 polymer material Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 claims description 7
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 claims description 6
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 claims description 6
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 claims description 6
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 6
- 230000000379 polymerizing effect Effects 0.000 claims description 6
- MDWVSAYEQPLWMX-UHFFFAOYSA-N 4,4'-Methylenebis(2,6-di-tert-butylphenol) Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 MDWVSAYEQPLWMX-UHFFFAOYSA-N 0.000 claims description 5
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
- 239000013638 trimer Substances 0.000 claims description 4
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 claims description 3
- 239000004913 cyclooctene Substances 0.000 claims description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 3
- CTYWXRDQWMRIIM-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)prop-2-enoic acid Chemical compound CC(C)(C)C1=CC(C=CC(O)=O)=CC(C(C)(C)C)=C1O CTYWXRDQWMRIIM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims 2
- 230000009477 glass transition Effects 0.000 description 22
- 239000000178 monomer Substances 0.000 description 9
- 229910052707 ruthenium Inorganic materials 0.000 description 8
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 7
- 239000003607 modifier Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000005649 metathesis reaction Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 5
- 239000004914 cyclooctane Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 230000005540 biological transmission Effects 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 238000007142 ring opening reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 3
- 229910052721 tungsten Inorganic materials 0.000 description 3
- 239000010937 tungsten Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- NGSWKAQJJWESNS-ZZXKWVIFSA-M 4-Hydroxycinnamate Natural products OC1=CC=C(\C=C\C([O-])=O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-M 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N C1NCCOC1 Chemical compound C1NCCOC1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- KFIIKQUXUBYHNP-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)prop-2-enoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)prop-2-enoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)prop-2-enoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C=CC(=O)OCC(COC(=O)C=CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)C=CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)C=CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 KFIIKQUXUBYHNP-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000005865 alkene metathesis reaction Methods 0.000 description 1
- PNPBGYBHLCEVMK-UHFFFAOYSA-N benzylidene(dichloro)ruthenium;tricyclohexylphosphanium Chemical compound Cl[Ru](Cl)=CC1=CC=CC=C1.C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1.C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1 PNPBGYBHLCEVMK-UHFFFAOYSA-N 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000002013 dioxins Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000011985 first-generation catalyst Substances 0.000 description 1
- 239000011984 grubbs catalyst Substances 0.000 description 1
- 239000013628 high molecular weight specie Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 239000005078 molybdenum compound Substances 0.000 description 1
- 150000002752 molybdenum compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- NGSWKAQJJWESNS-ZZXKWVIFSA-N trans-4-coumaric acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F232/08—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
- B01J2231/12—Olefin polymerisation or copolymerisation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/821—Ruthenium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2265—Carbenes or carbynes, i.e.(image)
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2265—Carbenes or carbynes, i.e.(image)
- B01J31/2269—Heterocyclic carbenes
- B01J31/2273—Heterocyclic carbenes with only nitrogen as heteroatomic ring members, e.g. 1,3-diarylimidazoline-2-ylidenes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2265—Carbenes or carbynes, i.e.(image)
- B01J31/2278—Complexes comprising two carbene ligands differing from each other, e.g. Grubbs second generation catalysts
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/13—Morphological aspects
- C08G2261/135—Cross-linked structures
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
- C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
- C08G2261/3325—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms derived from other polycyclic systems
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/40—Polymerisation processes
- C08G2261/41—Organometallic coupling reactions
- C08G2261/418—Ring opening metathesis polymerisation [ROMP]
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/70—Post-treatment
- C08G2261/74—Further polymerisation of the obtained polymers, e.g. living polymerisation to obtain block-copolymers
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/70—Post-treatment
- C08G2261/76—Post-treatment crosslinking
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
を有する化合物を触媒として用い、該触媒をジシクロペンタジエンと触媒/DCPDのモル比1:70000〜1:1000000でジシクロペンタジエンに混合し、重合が反応混合物を30〜200℃に加熱することにより行われ、また重合の前に溶液中に変性剤を導入してポリジシクロペンタジエンに基づくポリマー材料を調製し、その変性剤はシクロ−ペンタン、シクロ−オクタン、シクロ−オクタジエン、ノルボルネン、ノルボルナジエンのグループから選択されたいくつかのシクロ−オレフィンコ−モノマーの1または組合せでジシクロペンタジエンに基づいて5〜50重量%の量で用いることによって、達成される。シクロペンタジエンオリゴマーをジシクロペンタジエンの5〜65重量%の量はトリマーおよびテトラマーの混合物の形態で用いても良い。また、2塩基カルボン酸のエステル類、主としてジブチルフタレートおよびジオクチルフタレート、を変性剤としてジシクロペンタジエンの5〜25重量%の量で用い、ペンタエリスリトールテトラキス−(3,5−ジ−tert−ブチル−4−ヒドロキシ−シンナメート、4,4−メチレンビス(2,6−ジ−tert−ブチル−フェノール)、オクタデシル−3−(3,5−ジ−tert−ブチル−4−ヒドロキシ−フェニル)プロピオネートのグループから選択されるアルキルフェノールをジシクロペンタジエンの1〜5重量%の量で変性剤として用いても良い。変性剤として以下のグループ、シクロ−オレフィンおよび/またはシクロ−オレフィンとアルキル−フェノール;シクロ−オレフィンおよび2塩基カルボン酸のエステルとアルキルフェノール;2塩基カルボン酸のエステルとアルキルフェノールとの組合せを同時に導入してもよく、シクロ−オレフィンはシクロ−ペンタン、シクロ−オクテン、シクロ−オクタジエン、ノルボルネン、ノルボルナジエンでジシクロペンタジエンの5〜50重量%の量であり、アルキル−フェノールはペンタエリスリトールテトラキス−(3,5−ジ−tert−ブチル−4−ヒドロキシ−シンナメート、4,4−メチレンビス(2,6−ジ−tert−ブチル−フェノール)、オクタデシル−3−(3,5−ジ−tert−ブチル−4−ヒドロキシ−フェニル)プロピオネートであり、ジシクロペンタジエンの1〜5重量%の量であり、2塩基カルボン酸のエステルとアルキルフェノールはジブチルフタレートおよびジオクチルフタレートの群から選択され、ジシクロペンタジエンの5〜25重量%である。
Claims (6)
- ジシクロペンタジエン中に触媒を含む溶液、該溶液中に変性添加剤を導入することおよび反応混合物の重合を包含するポリジシクロペンタジエンに基づくポリマー材料の調製方法であって、触媒Nとして下記一般式:
を有する化合物を用い、該触媒をジシクロペンタジエンと触媒/ジシクロペンタジエンのモル比1:70000〜1:1000000で混合し、重合が反応混合物を30〜200℃に加熱することにより行われ、変性剤がシクロペンテン、シクロオクテン、シクロオクタジエン、ノルボルネン、ノルボルナジエンの群から選択された数種のシクロオレフィンコモノマーの1つまたは組合せであり、変性剤をシクロペンタジエンに対して5〜50重量%の量であることを特徴とする調製方法。 - ジシクロペンタジエン中に触媒を含む溶液、該溶液中に変性添加剤を導入することおよび反応混合物の重合を包含するジシクロペンタジエンに基づくポリマー材料の調製方法であって、触媒Nとして下記一般式:
を有する化合物を用い、該触媒をジシクロペンタジエンと触媒/ジシクロペンタジエンのモル比1:70000〜1:1000000で混合し、重合が反応混合物を30〜200℃に加熱することにより行われ、前記変性添加剤が2塩基カルボン酸のエステル、主として、ジブチルフタレートおよびジオクチルフタレートでジシクロペンタジエンの5〜25重量%であることを特徴とする調製方法。 - ジシクロペンタジエン中に触媒を含む溶液、該溶液中に変性添加剤を導入することおよび反応混合物の重合を包含するジシクロペンタジエンに基づくポリマー材料の調製方法であって、触媒Nとして下記一般式:
を有する化合物を用い、該触媒をジシクロペンタジエンと触媒/ジシクロペンタジエンのモル比1:70000〜1:1000000で混合し、重合が反応混合物を30〜200℃に加熱することにより行われ、前記変性添加剤がペンタエリスリトールテトラキス−(3,5−ジ−tert−ブチル−4−ヒドロキシ−シンナメート、4,4−メチレンビス(2,6−ジ−tert−ブチルフェノール)、オクタデシル3−(3,5−ジ−tert−ブチル4−ヒドロキシ−フェニル)プロピオネートの群から選択されるアルキルフェノールであり、ジシクロペンタジエンの1〜5重量%の量であることを特徴とする調製方法。 - ジシクロペンタジエン中に触媒を含む溶液、該溶液中に変性添加剤を導入することおよび反応混合物の重合を包含するジシクロペンタジエンに基づくポリマー材料の調製方法であって、触媒Nとして下記一般式:
を有する化合物を用い、該触媒をジシクロペンタジエンと触媒/ジシクロペンタジエンのモル比1:70000〜1:1000000で混合し、重合が反応混合物を30〜200℃に加熱することにより行われ、前記変性添加剤がシクロ−オレフィンおよび/またはシクロ−オレフィン類とアルキル−フェノール、シクロ−オレフィンと2塩基カルボン酸のエステルとアルキル−フェノール、2塩基カルボン酸のエステルとアルキル−フェノールのグループから選択された組合せで、シクロ−オレフィンはシクロ−ペンタン、シクロ−オクテン、シクロ−オクタジエン、ノルボルネン、ノルボルナジエンでジシクロペンタジエンの5〜50重量%の量であり、アルキル−フェノールはペンタエリスリトールテトラキス−(3,5−ジ−tert−ブチル−4−ヒドロキシ−シンナメート、4,4−メチレンビス(2,6−ジ−tert−ブチル−フェノール)、オクタデシル−3−(3,5−ジ−tert−ブチル−4−ヒドロキシ−フェニル)プロピオネートであり、ジシクロペンタジエンの1〜5重量%の量であり、2塩基カルボン酸のエステルとアルキルフェノールはジブチルフタレートおよびジオクチルフタレートの群から選択され、ジシクロペンタジエンの5〜25重量%であることを特徴とするポリジシクロペンタジエンの調製方法。
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