JPH0822892B2 - 架橋したジシクロペンタジエン重合体製造用の多液性の重合性組成物 - Google Patents
架橋したジシクロペンタジエン重合体製造用の多液性の重合性組成物Info
- Publication number
- JPH0822892B2 JPH0822892B2 JP2215088A JP21508890A JPH0822892B2 JP H0822892 B2 JPH0822892 B2 JP H0822892B2 JP 2215088 A JP2215088 A JP 2215088A JP 21508890 A JP21508890 A JP 21508890A JP H0822892 B2 JPH0822892 B2 JP H0822892B2
- Authority
- JP
- Japan
- Prior art keywords
- polymerizable composition
- composition according
- catalyst
- activator
- reactant
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 58
- 239000007788 liquid Substances 0.000 title claims description 35
- 229920000642 polymer Polymers 0.000 title claims description 31
- 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 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000003054 catalyst Substances 0.000 claims description 87
- 239000012190 activator Substances 0.000 claims description 43
- 239000000376 reactant Substances 0.000 claims description 42
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 20
- 229920001971 elastomer Polymers 0.000 claims description 19
- 239000000945 filler Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 238000005649 metathesis reaction Methods 0.000 claims description 16
- 229910052721 tungsten Inorganic materials 0.000 claims description 15
- 239000010937 tungsten Substances 0.000 claims description 15
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 14
- -1 alcohol compound Chemical class 0.000 claims description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000003607 modifier Substances 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 150000002989 phenols Chemical class 0.000 claims description 12
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical group [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 239000000806 elastomer Substances 0.000 claims description 10
- 239000005060 rubber Substances 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 8
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003381 stabilizer Substances 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 6
- 239000010456 wollastonite Substances 0.000 claims description 6
- 229910052882 wollastonite Inorganic materials 0.000 claims description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 claims description 5
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 claims description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- 239000002879 Lewis base Substances 0.000 claims description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical class CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- 150000007527 lewis bases Chemical group 0.000 claims description 4
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims description 4
- MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 claims description 4
- 239000000049 pigment Substances 0.000 claims description 4
- 150000002148 esters Chemical group 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 claims description 2
- XSXWOBXNYNULJG-UHFFFAOYSA-N 2-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=CC=C1O XSXWOBXNYNULJG-UHFFFAOYSA-N 0.000 claims description 2
- VSKJLJHPAFKHBX-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical compound CC(=C)C=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 VSKJLJHPAFKHBX-UHFFFAOYSA-N 0.000 claims description 2
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 claims description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 2
- 229920002943 EPDM rubber Polymers 0.000 claims description 2
- 244000043261 Hevea brasiliensis Species 0.000 claims description 2
- 239000005062 Polybutadiene Substances 0.000 claims description 2
- 229920002367 Polyisobutene Polymers 0.000 claims description 2
- QUMXDOLUJCHOAY-UHFFFAOYSA-N alpha-methylbenzyl acetate Natural products CC(=O)OC(C)C1=CC=CC=C1 QUMXDOLUJCHOAY-UHFFFAOYSA-N 0.000 claims description 2
- 229920005549 butyl rubber Polymers 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- 239000006229 carbon black Substances 0.000 claims description 2
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical group CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 claims description 2
- 239000010445 mica Substances 0.000 claims description 2
- 229910052618 mica group Inorganic materials 0.000 claims description 2
- 229920003052 natural elastomer Polymers 0.000 claims description 2
- 229920001194 natural rubber Polymers 0.000 claims description 2
- 229920002857 polybutadiene Polymers 0.000 claims description 2
- 229920001195 polyisoprene Polymers 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 2
- 239000013522 chelant Substances 0.000 claims 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims 1
- JFDZBHWFFUWGJE-KWCOIAHCSA-N benzonitrile Chemical group N#[11C]C1=CC=CC=C1 JFDZBHWFFUWGJE-KWCOIAHCSA-N 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 claims 1
- XAVQZBGEXVFCJI-UHFFFAOYSA-M lithium;phenoxide Chemical group [Li+].[O-]C1=CC=CC=C1 XAVQZBGEXVFCJI-UHFFFAOYSA-M 0.000 claims 1
- AFCAKJKUYFLYFK-UHFFFAOYSA-N tetrabutyltin Chemical compound CCCC[Sn](CCCC)(CCCC)CCCC AFCAKJKUYFLYFK-UHFFFAOYSA-N 0.000 claims 1
- KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 claims 1
- 239000000243 solution Substances 0.000 description 75
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 description 59
- 239000000178 monomer Substances 0.000 description 57
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 150000003658 tungsten compounds Chemical class 0.000 description 20
- 125000005234 alkyl aluminium group Chemical group 0.000 description 18
- 238000006116 polymerization reaction Methods 0.000 description 17
- 238000002156 mixing Methods 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 229920001187 thermosetting polymer Polymers 0.000 description 15
- 239000000654 additive Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 229920001519 homopolymer Polymers 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000008139 complexing agent Substances 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
- 150000002170 ethers Chemical class 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- ROQVLEJBZBDIMF-UHFFFAOYSA-N C.C=CC(C)(C)C=1C(=C(C=C(C=CC(=O)O)C1)C(C)(C)C)O.C=CC(C)(C)C=1C(=C(C=C(C=CC(=O)O)C1)C(C)(C)C)O.C=CC(C)(C)C=1C(=C(C=C(C=CC(=O)O)C1)C(C)(C)C)O.C=CC(C)(C)C=1C(=C(C=C(C=CC(=O)O)C1)C(C)(C)C)O Chemical compound C.C=CC(C)(C)C=1C(=C(C=C(C=CC(=O)O)C1)C(C)(C)C)O.C=CC(C)(C)C=1C(=C(C=C(C=CC(=O)O)C1)C(C)(C)C)O.C=CC(C)(C)C=1C(=C(C=C(C=CC(=O)O)C1)C(C)(C)C)O.C=CC(C)(C)C=1C(=C(C=C(C=CC(=O)O)C1)C(C)(C)C)O ROQVLEJBZBDIMF-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920002633 Kraton (polymer) Polymers 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000011954 Ziegler–Natta catalyst Substances 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HECLRDQVFMWTQS-HORUIINNSA-N bis[cyclopentadiene] Chemical compound C1C2[C@H]3CC=C[C@H]3C1C=C2 HECLRDQVFMWTQS-HORUIINNSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012612 commercial material Substances 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- CQYBWJYIKCZXCN-UHFFFAOYSA-N diethylaluminum Chemical compound CC[Al]CC CQYBWJYIKCZXCN-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 239000005337 ground glass Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 238000009863 impact test Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920006124 polyolefin elastomer Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010107 reaction injection moulding Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000003039 volatile agent Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Injection Moulding Of Plastics Or The Like (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34245582A | 1982-01-25 | 1982-01-25 | |
| US342455 | 1982-01-25 | ||
| US342453 | 1982-01-25 | ||
| US06/342,453 US4400340A (en) | 1982-01-25 | 1982-01-25 | Method for making a dicyclopentadiene thermoset polymer |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58009448A Division JPS58129013A (ja) | 1982-01-25 | 1983-01-25 | 架橋したジシクロペンタジエンポリマーからなる成形物の製造方法 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4113623A Division JP2509047B2 (ja) | 1982-01-25 | 1992-05-06 | ジシクロペンタジエン重合体を含有する組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03205409A JPH03205409A (ja) | 1991-09-06 |
| JPH0822892B2 true JPH0822892B2 (ja) | 1996-03-06 |
Family
ID=26993015
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2215088A Expired - Lifetime JPH0822892B2 (ja) | 1982-01-25 | 1990-08-16 | 架橋したジシクロペンタジエン重合体製造用の多液性の重合性組成物 |
| JP2215089A Granted JPH03223310A (ja) | 1982-01-25 | 1990-08-16 | 架橋したジシクロペンタジエンポリマーからなる成形物の製造方法 |
| JP4113623A Expired - Lifetime JP2509047B2 (ja) | 1982-01-25 | 1992-05-06 | ジシクロペンタジエン重合体を含有する組成物 |
| JP7027273A Pending JPH07268082A (ja) | 1982-01-25 | 1995-01-24 | 架橋したジシクロペンタジエンポリマーからなる成形物の製造法 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2215089A Granted JPH03223310A (ja) | 1982-01-25 | 1990-08-16 | 架橋したジシクロペンタジエンポリマーからなる成形物の製造方法 |
| JP4113623A Expired - Lifetime JP2509047B2 (ja) | 1982-01-25 | 1992-05-06 | ジシクロペンタジエン重合体を含有する組成物 |
| JP7027273A Pending JPH07268082A (ja) | 1982-01-25 | 1995-01-24 | 架橋したジシクロペンタジエンポリマーからなる成形物の製造法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4584425A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0084888B2 (cg-RX-API-DMAC7.html) |
| JP (4) | JPH0822892B2 (cg-RX-API-DMAC7.html) |
| DE (1) | DE3372102D1 (cg-RX-API-DMAC7.html) |
| MY (1) | MY103052A (cg-RX-API-DMAC7.html) |
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| GB9117744D0 (en) * | 1991-08-16 | 1991-10-02 | Shell Int Research | Polymerization of cycloolefins and catalytic system suitable for use therein |
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| US5939504A (en) * | 1995-12-07 | 1999-08-17 | Advanced Polymer Technologies | Method for extending the pot life of an olefin metathesis polymerization reaction |
| US6020443A (en) * | 1996-02-08 | 2000-02-01 | Advanced Polymer Technologies, Inc. | Polymerization of low grade DCPD monomers using an olefin metathesis catalyst |
| DE59701556D1 (de) * | 1996-03-07 | 2000-06-08 | Ciba Sc Holding Ag | Härtbare Zusammensetzung enthaltend ein Diels-Alder-Addukt von Cyclopentadien und einen Füllstoff |
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| CA2246155A1 (en) * | 1997-09-05 | 1999-03-05 | Michael A. Giardello | Metathesis polymerized olefin articles containing flame-retarding agents |
| US6271299B1 (en) * | 1999-02-02 | 2001-08-07 | Dow Corning Corporation | Fire resistant sealant composition |
| JP2003025364A (ja) * | 2001-07-16 | 2003-01-29 | Nippon Petrochemicals Co Ltd | メタセシス重合性モノマーの重合による架橋重合体成形物の製造方法 |
| JP4781568B2 (ja) * | 2001-07-16 | 2011-09-28 | Ｊｘ日鉱日石エネルギー株式会社 | メタセシス重合性モノマーの反応性溶液並びに架橋重合体成形物およびその製造方法 |
| US7645443B2 (en) * | 2004-11-15 | 2010-01-12 | Kerr Corporation | Polyether-based composition curable by metathesis reaction |
| US7625551B2 (en) * | 2004-11-15 | 2009-12-01 | Kerr Corporation | Polyether-based dental impression material curable by metathesis reaction |
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| WO2006126612A1 (ja) * | 2005-05-25 | 2006-11-30 | Jsr Corporation | 金属ヒドリド錯体、環状オレフィン系開環重合体の水素化方法および環状オレフィン系開環重合体水素化物の製造方法 |
| JP2007246900A (ja) * | 2006-02-21 | 2007-09-27 | Kerr Corp | 官能性オレフィン基で末端封止されたアルコキシ−シロキサンポリエーテルカルボキシレートの製造方法 |
| KR100766466B1 (ko) * | 2006-07-05 | 2007-10-12 | 주식회사 남경알앤디 | 열경화성 폴리디시클로펜타디엔 복합체 분말을 이용한성형품의 제조방법 |
| WO2008010973A1 (en) * | 2006-07-18 | 2008-01-24 | Dow Global Technologies, Inc. | Method for preparing poly(dicyclopentadiene) |
| KR101159304B1 (ko) * | 2008-12-30 | 2012-06-26 | 주식회사 도하인더스트리 | 인시츄 복분해 중합을 이용한 ｌ-ｐｄｃｐｄ/실리케이트 하이브리드 나노복합체 제조방법 |
| KR101291379B1 (ko) * | 2011-03-25 | 2013-07-30 | 한국화학연구원 | 글리콜형 노보넨 에스터계 유도체 및 이의 용도 |
| ES2805289T3 (es) | 2011-06-17 | 2021-02-11 | Materia Inc | Promotores de la adherencia y modificadores de la gelificación para composiciones de metátesis de olefinas |
| CN104428059A (zh) * | 2012-05-22 | 2015-03-18 | 陶氏环球技术有限责任公司 | 处理二环戊二烯单体的方法 |
| JPWO2015098620A1 (ja) * | 2013-12-26 | 2017-03-23 | 日本ゼオン株式会社 | 重合性組成物の製造方法 |
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-
1983
- 1983-01-25 DE DE8383100645T patent/DE3372102D1/de not_active Expired
- 1983-01-25 EP EP83100645A patent/EP0084888B2/en not_active Expired - Lifetime
-
1984
- 1984-11-16 US US06/672,424 patent/US4584425A/en not_active Expired - Lifetime
-
1988
- 1988-02-02 MY MYPI88000088A patent/MY103052A/en unknown
-
1990
- 1990-08-16 JP JP2215088A patent/JPH0822892B2/ja not_active Expired - Lifetime
- 1990-08-16 JP JP2215089A patent/JPH03223310A/ja active Granted
-
1992
- 1992-05-06 JP JP4113623A patent/JP2509047B2/ja not_active Expired - Lifetime
-
1995
- 1995-01-24 JP JP7027273A patent/JPH07268082A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| MY103052A (en) | 1993-04-30 |
| JP2509047B2 (ja) | 1996-06-19 |
| JPH06145247A (ja) | 1994-05-24 |
| JPH049812B2 (cg-RX-API-DMAC7.html) | 1992-02-21 |
| US4584425A (en) | 1986-04-22 |
| EP0084888A1 (en) | 1983-08-03 |
| JPH03223310A (ja) | 1991-10-02 |
| DE3372102D1 (en) | 1987-07-23 |
| EP0084888B1 (en) | 1987-06-16 |
| JPH03205409A (ja) | 1991-09-06 |
| JPH07268082A (ja) | 1995-10-17 |
| EP0084888B2 (en) | 1995-10-25 |
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