JP5303281B2 - 開環メタセシス重合によって得られる固体材料 - Google Patents
開環メタセシス重合によって得られる固体材料 Download PDFInfo
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- JP5303281B2 JP5303281B2 JP2008553315A JP2008553315A JP5303281B2 JP 5303281 B2 JP5303281 B2 JP 5303281B2 JP 2008553315 A JP2008553315 A JP 2008553315A JP 2008553315 A JP2008553315 A JP 2008553315A JP 5303281 B2 JP5303281 B2 JP 5303281B2
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- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 title claims description 79
- 239000011343 solid material Substances 0.000 title claims description 25
- 239000000203 mixture Substances 0.000 claims description 110
- 239000000945 filler Substances 0.000 claims description 47
- 239000000178 monomer Substances 0.000 claims description 41
- 239000003999 initiator Substances 0.000 claims description 40
- 238000003801 milling Methods 0.000 claims description 34
- 239000000463 material Substances 0.000 claims description 33
- -1 propylbutyl Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 17
- 239000000126 substance Chemical group 0.000 claims description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 238000005496 tempering Methods 0.000 claims description 15
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- 239000002131 composite material Substances 0.000 claims description 13
- 125000000524 functional group Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229910052707 ruthenium Inorganic materials 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
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- 230000000977 initiatory effect Effects 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 239000003446 ligand Substances 0.000 claims description 7
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000005452 bending Methods 0.000 claims description 6
- 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 claims description 6
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 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 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 230000006872 improvement Effects 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 5
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- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 3
- 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 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
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- 239000004917 carbon fiber Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 229930007927 cymene Natural products 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
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- 125000004957 naphthylene group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims description 3
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- RBORBHYCVONNJH-UHFFFAOYSA-K yttrium(iii) fluoride Chemical compound F[Y](F)F RBORBHYCVONNJH-UHFFFAOYSA-K 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 10
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- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 9
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- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 5
- 239000005548 dental material Substances 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000004042 decolorization Methods 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
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- 239000012784 inorganic fiber Substances 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
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- JANXZPFHGIMWSD-UHFFFAOYSA-N 7-oxabicyclo[2.2.1]hept-3-ene Chemical class C1C(O2)CCC2=C1 JANXZPFHGIMWSD-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
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- 150000001298 alcohols Chemical class 0.000 description 2
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- 239000003054 catalyst Substances 0.000 description 2
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- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 2
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 2
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- 238000002845 discoloration Methods 0.000 description 2
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- 150000004706 metal oxides Chemical class 0.000 description 2
- 238000005649 metathesis reaction Methods 0.000 description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical group [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
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- 125000006850 spacer group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- XDRAKJQFCQVBMP-UHFFFAOYSA-N 2-but-2-enyl-3-methylbutanedioic acid Chemical compound CC=CCC(C(O)=O)C(C)C(O)=O XDRAKJQFCQVBMP-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- YCNYCBYHUAGZIZ-UHFFFAOYSA-N 7-oxabicyclo[2.2.1]hept-2-ene Chemical compound O1C2CCC1C=C2 YCNYCBYHUAGZIZ-UHFFFAOYSA-N 0.000 description 1
- ZHNWKGCTEBVPNS-UHFFFAOYSA-N 7-oxabicyclo[2.2.1]hept-2-ene Chemical compound O1C2CCC1C=C2.O1C2CCC1C=C2 ZHNWKGCTEBVPNS-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 241000183024 Populus tremula Species 0.000 description 1
- 239000012327 Ruthenium complex Substances 0.000 description 1
- 241000872198 Serjania polyphylla Species 0.000 description 1
- 208000032005 Spinocerebellar ataxia with axonal neuropathy type 2 Diseases 0.000 description 1
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
- HMDDXIMCDZRSNE-UHFFFAOYSA-N [C].[Si] Chemical compound [C].[Si] HMDDXIMCDZRSNE-UHFFFAOYSA-N 0.000 description 1
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- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 229910052789 astatine Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 208000033361 autosomal recessive with axonal neuropathy 2 spinocerebellar ataxia Diseases 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
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- MKOSBHNWXFSHSW-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-en-5-ol Chemical compound C1C2C(O)CC1C=C2 MKOSBHNWXFSHSW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000013590 bulk material Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
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- 238000009833 condensation Methods 0.000 description 1
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- 229920001577 copolymer Polymers 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
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- 238000003701 mechanical milling Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- RNYFPCBPUJIHRR-WCZCRHMRSA-N norbornenylethyl-poss® Chemical group C1([C@@H]2C[C@@H](C=C2)C1)CC[Si](O1)(O2)O[Si](O3)(C4CCCC4)O[Si](O4)(C5CCCC5)O[Si]1(C1CCCC1)O[Si](O1)(C5CCCC5)O[Si]2(C2CCCC2)O[Si]3(C2CCCC2)O[Si]41C1CCCC1 RNYFPCBPUJIHRR-WCZCRHMRSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000002186 photoactivation Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
Landscapes
- Health & Medical Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dental Preparations (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Saccharide Compounds (AREA)
- Oscillators With Electromechanical Resonators (AREA)
- Stored Programmes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06002150.8 | 2006-02-02 | ||
| EP06002150A EP1815838B1 (en) | 2006-02-02 | 2006-02-02 | Solid materials obtainable by the ring-opening methathesis polymerization |
| PCT/US2007/002576 WO2007089801A1 (en) | 2006-02-02 | 2007-01-30 | Solid materials obtainable by ring-opening metathesis polymerization |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009525339A JP2009525339A (ja) | 2009-07-09 |
| JP2009525339A5 JP2009525339A5 (enExample) | 2010-03-04 |
| JP5303281B2 true JP5303281B2 (ja) | 2013-10-02 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2008553315A Expired - Fee Related JP5303281B2 (ja) | 2006-02-02 | 2007-01-30 | 開環メタセシス重合によって得られる固体材料 |
Country Status (6)
| Country | Link |
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| US (1) | US8178604B2 (enExample) |
| EP (1) | EP1815838B1 (enExample) |
| JP (1) | JP5303281B2 (enExample) |
| AT (1) | ATE480216T1 (enExample) |
| DE (1) | DE602006016722D1 (enExample) |
| WO (1) | WO2007089801A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE602006016722D1 (de) | 2006-02-02 | 2010-10-21 | 3M Innovative Properties Co | Durch ROMP erhältliche Feststoffe |
| EP1942125A1 (en) * | 2006-12-20 | 2008-07-09 | 3M Innovative Properties Company | Compositions curable by ring opening metathesis polymerarization at low temperatures and their application in the dental field |
| RU2565414C2 (ru) | 2010-05-25 | 2015-10-20 | 3М Инновейтив Пропертиз Компани | Метод обработки поверхности частиц неорганического оксида, твердеющие стоматологические композиты, частицы с обработанной поверхностью и соединения для обработки поверхности |
| US9044292B2 (en) | 2010-08-11 | 2015-06-02 | 3M Innovative Properties Company | Dental articles including a ceramic and microparticle coating and method of making the same |
| EP2603159A1 (en) | 2010-08-11 | 2013-06-19 | 3M Innovative Properties Company | Aesthetic and abrasion resistant coated dental articles and methods of making the same |
| DE102012202005A1 (de) * | 2011-10-12 | 2013-04-18 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Gefüllte und ungefüllte, organisch modifizierte, gegebenenfalls organisch vernetzte Kieselsäure(hetero)polysilikate als Dentalmaterialien für die "Chairside"-Behandlung |
| EP3955881B1 (en) * | 2019-04-15 | 2024-04-24 | Dentsply Sirona Inc. | Dental composition |
| WO2023244364A1 (en) * | 2022-06-14 | 2023-12-21 | Board Of Regents, The University Of Texas System | Cyclic olefin polymer having high cis double bond content |
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| US4380617A (en) | 1982-01-20 | 1983-04-19 | The B. F. Goodrich Company | Preparation of polymers from cycloolefins |
| US4426502A (en) | 1982-06-14 | 1984-01-17 | The B. F. Goodrich Company | Bulk polymerization of cycloolefins |
| JPS63128063A (ja) * | 1986-11-18 | 1988-05-31 | Mitsubishi Petrochem Co Ltd | ポリフエニレンテ−テル樹脂組成物 |
| JPH07116356B2 (ja) * | 1986-11-18 | 1995-12-13 | 三菱化学株式会社 | ポリフエニレンエーテル樹脂組成物 |
| DE4029230C2 (de) | 1990-09-14 | 1995-03-23 | Ivoclar Ag | Polymerisierbarer Dentalwerkstoff |
| JP3205409B2 (ja) | 1992-12-28 | 2001-09-04 | 株式会社竹中工務店 | 蓄熱空調システム |
| CZ69696A3 (en) * | 1993-09-10 | 1996-06-12 | Ciba Geigy Ag | Polymerization process of cyclic olefins and a polymerizable mixture |
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| US5973085A (en) * | 1994-11-17 | 1999-10-26 | Ciba Specialty Chemicals Corporation | Monomers and composition which can be crosslinked and crosslinked polymers |
| RU2168518C2 (ru) * | 1994-12-23 | 2001-06-10 | Циба Спешиалти Чемикалс Холдинг Инк. | Состав, способный к полимеризации |
| ES2210393T3 (es) * | 1995-10-19 | 2004-07-01 | Ciba Specialty Chemicals Holding Inc. | Composicion polimerizable y metodo de polimerizacion. |
| DE59610089D1 (de) * | 1995-11-02 | 2003-03-06 | Ciba Sc Holding Ag | Härtbare Zusammensetzung enthaltend Cycloolefin, Silan und Füllstoff |
| AU2091997A (en) | 1996-03-04 | 1997-09-22 | Ciba Specialty Chemicals Holding Inc. | Polymerizable composition |
| WO1999011958A2 (en) * | 1997-09-05 | 1999-03-11 | A. O. Smith Corporation | Pipe made from metathesis polymerized olefins |
| DE19742981B4 (de) * | 1997-09-29 | 2013-07-25 | 3M Deutschland Gmbh | Durch ROMP härtbare Dentalmassen |
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| US6455029B1 (en) * | 2000-10-17 | 2002-09-24 | Kerr Corporation | Dental impression material utilizing ruthenium catalyst |
| US6649146B2 (en) * | 2000-10-17 | 2003-11-18 | Kerr Corporation | Dental impression material utilizing ruthenium metathesis catalyst |
| DE10205005A1 (de) * | 2002-02-07 | 2003-08-21 | Neumag Gmbh & Co Kg | Verfahren und Vorrichtung zum Benetzen eines laufenden Filamentbündels |
| DE60328287D1 (de) | 2002-05-06 | 2009-08-20 | Kerr Corp | Durch eine metathesereaktion härtbare zusammensetzung |
| DE10222551A1 (de) * | 2002-05-17 | 2003-11-27 | Bayer Ag | Neue Übergangsmetall-Komplexe und deren Einsatz in Übergangsmetall-katalysierten Reaktionen |
| PL199412B1 (pl) | 2002-10-15 | 2008-09-30 | Boehringer Ingelheim Int | Nowe kompleksy rutenu jako (pre)katalizatory reakcji metatezy, pochodne 2-alkoksy-5-nitrostyrenu jako związki pośrednie i sposób ich wytwarzania |
| US7173097B2 (en) * | 2003-05-06 | 2007-02-06 | Kerr Corporation | Metathesis-curable composition with a reaction control agent |
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| EP1543875A1 (en) | 2003-12-04 | 2005-06-22 | Boehringer Ingelheim Pharma GmbH & Co. KG | Novel metathesis ruthenium catalyst |
| DE102004002178A1 (de) * | 2004-01-15 | 2005-08-11 | Ivoclar Vivadent Ag | Dentalmeterialien auf der Basis von RÖMP-Kompositen |
| ATE519473T1 (de) * | 2004-06-30 | 2011-08-15 | Ivoclar Vivadent Ag | Dentalmaterialien, erhalten durch photoinduzierte ring-öffnungs-metathese-polymerisation von cyclischen olefinen |
| US7001590B1 (en) * | 2004-11-15 | 2006-02-21 | Kerr Corporation | Metathesis-curable composition |
| DE602006016722D1 (de) | 2006-02-02 | 2010-10-21 | 3M Innovative Properties Co | Durch ROMP erhältliche Feststoffe |
| EP1942125A1 (en) * | 2006-12-20 | 2008-07-09 | 3M Innovative Properties Company | Compositions curable by ring opening metathesis polymerarization at low temperatures and their application in the dental field |
-
2006
- 2006-02-02 DE DE602006016722T patent/DE602006016722D1/de active Active
- 2006-02-02 EP EP06002150A patent/EP1815838B1/en not_active Revoked
- 2006-02-02 AT AT06002150T patent/ATE480216T1/de not_active IP Right Cessation
-
2007
- 2007-01-30 US US12/162,429 patent/US8178604B2/en active Active
- 2007-01-30 JP JP2008553315A patent/JP5303281B2/ja not_active Expired - Fee Related
- 2007-01-30 WO PCT/US2007/002576 patent/WO2007089801A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007089801A1 (en) | 2007-08-09 |
| DE602006016722D1 (de) | 2010-10-21 |
| EP1815838B1 (en) | 2010-09-08 |
| EP1815838A1 (en) | 2007-08-08 |
| JP2009525339A (ja) | 2009-07-09 |
| ATE480216T1 (de) | 2010-09-15 |
| US20090088494A1 (en) | 2009-04-02 |
| US8178604B2 (en) | 2012-05-15 |
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