JP2003525311A - ノルボルネンスルホンアミドポリマーの製造法 - Google Patents
ノルボルネンスルホンアミドポリマーの製造法Info
- Publication number
- JP2003525311A JP2003525311A JP2000597337A JP2000597337A JP2003525311A JP 2003525311 A JP2003525311 A JP 2003525311A JP 2000597337 A JP2000597337 A JP 2000597337A JP 2000597337 A JP2000597337 A JP 2000597337A JP 2003525311 A JP2003525311 A JP 2003525311A
- Authority
- JP
- Japan
- Prior art keywords
- group
- branched
- alkyl
- catalyst
- linear
- 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.)
- Pending
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 135
- -1 norbornene sulfonamide Chemical class 0.000 title claims abstract description 122
- 229940124530 sulfonamide Drugs 0.000 title claims abstract description 33
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 109
- 239000000178 monomer Substances 0.000 claims abstract description 70
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims abstract description 12
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000005977 Ethylene Substances 0.000 claims abstract description 5
- 238000005649 metathesis reaction Methods 0.000 claims abstract description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 74
- 239000000126 substance Substances 0.000 claims description 57
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 56
- 229910052751 metal Inorganic materials 0.000 claims description 52
- 239000002184 metal Substances 0.000 claims description 52
- 229910052799 carbon Inorganic materials 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 150000001450 anions Chemical class 0.000 claims description 38
- 229910052763 palladium Inorganic materials 0.000 claims description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 34
- 239000003446 ligand Substances 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 32
- 239000001257 hydrogen Chemical group 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 150000001768 cations Chemical class 0.000 claims description 22
- 238000006116 polymerization reaction Methods 0.000 claims description 21
- 125000000565 sulfonamide group Chemical group 0.000 claims description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 125000004122 cyclic group Chemical group 0.000 claims description 17
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 15
- 229910052759 nickel Inorganic materials 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 229930195733 hydrocarbon Natural products 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims description 11
- 125000003367 polycyclic group Chemical group 0.000 claims description 11
- 150000003456 sulfonamides Chemical class 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 230000007935 neutral effect Effects 0.000 claims description 10
- 229910021645 metal ion Inorganic materials 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 150000004292 cyclic ethers Chemical class 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 6
- 230000000379 polymerizing effect Effects 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- 229910052723 transition metal Inorganic materials 0.000 claims description 6
- 239000007848 Bronsted acid Substances 0.000 claims description 5
- 239000002841 Lewis acid Substances 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 150000004820 halides Chemical group 0.000 claims description 5
- 150000007517 lewis acids Chemical class 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 150000003624 transition metals Chemical class 0.000 claims description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 4
- 239000010941 cobalt Chemical group 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
- 150000003997 cyclic ketones Chemical class 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 150000002596 lactones Chemical class 0.000 claims description 4
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 238000012644 addition polymerization Methods 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- 150000004796 dialkyl magnesium compounds Chemical class 0.000 claims description 3
- 150000005826 halohydrocarbons Chemical class 0.000 claims description 3
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 125000002577 pseudohalo group Chemical group 0.000 claims description 3
- 238000007142 ring opening reaction Methods 0.000 claims description 3
- FOIBDFKNELQUBW-UHFFFAOYSA-N [Ru]=CC1=CC=CC=C1.C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 Chemical compound [Ru]=CC1=CC=CC=C1.C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 FOIBDFKNELQUBW-UHFFFAOYSA-N 0.000 claims description 2
- 230000002411 adverse Effects 0.000 claims description 2
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 150000002848 norbornenes Chemical class 0.000 claims description 2
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 claims description 2
- 125000002524 organometallic group Chemical group 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 1
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- 230000014509 gene expression Effects 0.000 claims 1
- 150000005671 trienes Chemical class 0.000 claims 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 abstract description 19
- 229920001577 copolymer Polymers 0.000 abstract description 17
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 abstract description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 102
- 239000000243 solution Substances 0.000 description 91
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 62
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
- 238000006243 chemical reaction Methods 0.000 description 37
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 30
- 238000003756 stirring Methods 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 25
- 238000005481 NMR spectroscopy Methods 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 23
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000004821 distillation Methods 0.000 description 18
- 229920001429 chelating resin Polymers 0.000 description 17
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 150000002431 hydrogen Chemical class 0.000 description 15
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 14
- 229910052731 fluorine Inorganic materials 0.000 description 14
- KJUJWQKOLRDCCH-UHFFFAOYSA-N n-(5-bicyclo[2.2.1]hept-2-enylmethyl)propane-1-sulfonamide Chemical compound C1C2C(CNS(=O)(=O)CCC)CC1C=C2 KJUJWQKOLRDCCH-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 13
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 12
- 239000013522 chelant Substances 0.000 description 12
- 239000011737 fluorine Substances 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- 239000003456 ion exchange resin Substances 0.000 description 12
- 229920003303 ion-exchange polymer Polymers 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 229910001868 water Inorganic materials 0.000 description 12
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 11
- 229910052786 argon Inorganic materials 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 9
- 239000012986 chain transfer agent Substances 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- 239000012429 reaction media Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 238000012546 transfer Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical compound [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- PERLSLNQWLZSLS-UHFFFAOYSA-N ethyl hexanoate;nickel Chemical compound [Ni].CCCCCC(=O)OCC PERLSLNQWLZSLS-UHFFFAOYSA-N 0.000 description 6
- 150000002736 metal compounds Chemical class 0.000 description 6
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 238000004566 IR spectroscopy Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- JEPPYVOSGKWVSJ-UHFFFAOYSA-N bicyclo[2.2.1]heptan-3-amine Chemical compound C1CC2C(N)CC1C2 JEPPYVOSGKWVSJ-UHFFFAOYSA-N 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- FEALMIYDTDFJBH-UHFFFAOYSA-N n-(5-bicyclo[2.2.1]hept-2-enylmethyl)methanesulfonamide Chemical compound C1C2C(CNS(=O)(=O)C)CC1C=C2 FEALMIYDTDFJBH-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 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 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 150000004678 hydrides Chemical class 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- 238000012021 retail method of payment Methods 0.000 description 1
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- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- FCQRKDSALKMOGU-UHFFFAOYSA-K rhodium(3+);triphenylphosphane;trichloride Chemical compound Cl[Rh](Cl)Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 FCQRKDSALKMOGU-UHFFFAOYSA-K 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910001544 silver hexafluoroantimonate(V) Inorganic materials 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 125000004079 stearyl 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])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])[H] 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical compound [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical class S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 229910052815 sulfur oxide Inorganic materials 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 125000002469 tricosyl 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])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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SWLICCIRFBHLJN-UHFFFAOYSA-N tricyclohexylphosphanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1 SWLICCIRFBHLJN-UHFFFAOYSA-N 0.000 description 1
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-O trioctylazanium Chemical compound CCCCCCCC[NH+](CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-O 0.000 description 1
- AXVOAMVQOCBPQT-UHFFFAOYSA-N triphos Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 AXVOAMVQOCBPQT-UHFFFAOYSA-N 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- NBEBUJZPHJHXOM-UHFFFAOYSA-N tris(2-bicyclo[2.2.1]heptanyl)alumane Chemical compound C1CC2CC1CC2[Al](C1CC2CCC1C2)C1CC2CCC1C2 NBEBUJZPHJHXOM-UHFFFAOYSA-N 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
-
- 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
-
- 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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Polyethers (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11893699P | 1999-02-05 | 1999-02-05 | |
| US60/118,936 | 1999-02-05 | ||
| US09/497,356 | 2000-02-03 | ||
| US09/497,356 US6235849B1 (en) | 1999-02-05 | 2000-02-03 | Method of preparing norbornene sulfonamide polymers |
| PCT/US2000/003060 WO2000046267A1 (en) | 1999-02-05 | 2000-02-04 | Method of preparing norbornene sulfonamide polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003525311A true JP2003525311A (ja) | 2003-08-26 |
| JP2003525311A5 JP2003525311A5 (https=) | 2011-02-03 |
Family
ID=22381647
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000597337A Pending JP2003525311A (ja) | 1999-02-05 | 2000-02-04 | ノルボルネンスルホンアミドポリマーの製造法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6235849B1 (https=) |
| EP (1) | EP1157058B1 (https=) |
| JP (1) | JP2003525311A (https=) |
| KR (1) | KR100687963B1 (https=) |
| AT (1) | ATE243719T1 (https=) |
| AU (1) | AU2757300A (https=) |
| DE (1) | DE60003529T2 (https=) |
| WO (1) | WO2000046267A1 (https=) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003040929A (ja) * | 2001-07-27 | 2003-02-13 | Jsr Corp | 環状オレフィン付加重合体の製造方法 |
| JP2003040930A (ja) * | 2001-07-27 | 2003-02-13 | Jsr Corp | 環状オレフィン付加重合体の製造方法 |
| JP2005171234A (ja) * | 2003-11-18 | 2005-06-30 | Jsr Corp | 新規な（共）重合体およびその製造方法並びにカルボキシル基含有（共）重合体の製造方法 |
| JP2006111733A (ja) * | 2004-10-14 | 2006-04-27 | Tokyo Ohka Kogyo Co Ltd | 高分子化合物、ポジ型レジスト組成物およびレジストパターン形成方法 |
| WO2006064814A1 (ja) * | 2004-12-15 | 2006-06-22 | Nihon University | ノルボルネン系付加（共）重合体の製造方法 |
| JP2007091634A (ja) * | 2005-09-28 | 2007-04-12 | Central Glass Co Ltd | α−置換アクリル酸ノルボルナニル類の製造方法 |
| JP2007534796A (ja) * | 2004-02-23 | 2007-11-29 | ランクセス・インコーポレーテッド | 低分子量ニトリルゴムの調製方法 |
| JP2008050342A (ja) * | 2006-07-26 | 2008-03-06 | Central Glass Co Ltd | Ｎ−（ビシクロ［２，２，１］ヘプト−５−エン−２−イルメチル）−１，１，１−トリフルオロメタンスルホンアミドの製造方法 |
| WO2008099725A1 (ja) * | 2007-02-15 | 2008-08-21 | Tokyo Ohka Kogyo Co., Ltd. | 高分子化合物、レジスト組成物及びレジストパターン形成方法 |
| JP2008536956A (ja) * | 2005-02-22 | 2008-09-11 | プロメラス， エルエルシー | ノルボルネン系ポリマー、その組成物、及び該組成物を使用するリソグラフィ法 |
| JP2009096767A (ja) * | 2007-10-18 | 2009-05-07 | Kuraray Co Ltd | スルホニルハライド誘導体の製造方法 |
| JP2010083873A (ja) * | 2008-09-02 | 2010-04-15 | Kuraray Co Ltd | スルトン誘導体の製造方法 |
| JP2010132664A (ja) * | 2009-12-28 | 2010-06-17 | Tokyo Ohka Kogyo Co Ltd | 新規な化合物、及びその製造方法、並びに高分子化合物 |
| US8021824B2 (en) | 2007-02-15 | 2011-09-20 | Tokyo Ohka Kogyo Co., Ltd. | Polymer compound, resist composition and method of forming resist pattern |
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|---|---|---|---|---|
| US6887956B2 (en) | 2000-10-12 | 2005-05-03 | Dow Global Technologies Inc. | Catalyst system for high-cis polybutadiene |
| KR20020056602A (ko) * | 2000-12-29 | 2002-07-10 | 노기호 | 황을 포함하는 고리형 올레핀 공중합체 및 그의 제조방법 |
| US6583307B2 (en) * | 2001-03-07 | 2003-06-24 | University Of New Orleans Research And Technology Foundation, Inc. | Convenient and efficient Suzuki-Miyaura cross-coupling catalyzed by a palladium/diazabutadiene system |
| WO2004037866A2 (en) | 2002-10-21 | 2004-05-06 | Shipley Company L.L.C. | Photoresists containing sulfonamide component |
| US6677419B1 (en) | 2002-11-13 | 2004-01-13 | International Business Machines Corporation | Preparation of copolymers |
| EP1589055A4 (en) * | 2003-01-31 | 2010-06-02 | Zeon Corp | METHOD FOR THE PRODUCTION OF A CYCLOOLEFIN RESIN FILM AND METHOD FOR THE PRODUCTION OF A CYCLOOLEFIN RESIN FILM OR A CYCLOOLEFIN RESIN FILM |
| US6949325B2 (en) * | 2003-09-16 | 2005-09-27 | International Business Machines Corporation | Negative resist composition with fluorosulfonamide-containing polymer |
| US7063931B2 (en) * | 2004-01-08 | 2006-06-20 | International Business Machines Corporation | Positive photoresist composition with a polymer including a fluorosulfonamide group and process for its use |
| ATE414118T1 (de) * | 2004-07-07 | 2008-11-15 | Promerus Llc | Lichtempfindliche dielektrische harzzusammensetzungen und ihre verwendungen |
| US7799883B2 (en) * | 2005-02-22 | 2010-09-21 | Promerus Llc | Norbornene-type polymers, compositions thereof and lithographic process using such compositions |
| CN100344656C (zh) * | 2006-05-11 | 2007-10-24 | 复旦大学 | 聚降冰片烯的制备方法 |
| US20080027246A1 (en) * | 2006-07-26 | 2008-01-31 | Andrew Bell | Process for forming perfluorinated-alkyl sulfonamide substituted norbornene-type monomers |
| US8541523B2 (en) * | 2010-04-05 | 2013-09-24 | Promerus, Llc | Norbornene-type polymers, compositions thereof and lithographic process using such compositions |
| CN102702432B (zh) * | 2012-05-30 | 2014-06-18 | 宁波工程学院 | 用于降冰片烯、马来酸酐与环己烯三元共聚的催化剂以及三元共聚方法 |
| CN105218821A (zh) * | 2015-10-19 | 2016-01-06 | 昆明理工大学 | 一种聚合单体与二氧化硫共聚物的制备方法 |
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- 2000-02-03 US US09/497,356 patent/US6235849B1/en not_active Expired - Lifetime
- 2000-02-04 WO PCT/US2000/003060 patent/WO2000046267A1/en not_active Ceased
- 2000-02-04 AT AT00905995T patent/ATE243719T1/de not_active IP Right Cessation
- 2000-02-04 AU AU27573/00A patent/AU2757300A/en not_active Abandoned
- 2000-02-04 KR KR1020017009927A patent/KR100687963B1/ko not_active Expired - Fee Related
- 2000-02-04 EP EP00905995A patent/EP1157058B1/en not_active Expired - Lifetime
- 2000-02-04 JP JP2000597337A patent/JP2003525311A/ja active Pending
- 2000-02-04 DE DE60003529T patent/DE60003529T2/de not_active Expired - Lifetime
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| JPH06271527A (ja) * | 1993-03-15 | 1994-09-27 | Kuraray Co Ltd | ３−フェニルスルホニルアミノ−ビシクロ［２，２，１］ヘプタン−２−カルボン酸アルキルエステルの製造方法 |
| JPH0990638A (ja) * | 1995-03-07 | 1997-04-04 | At & T Corp | エネルギー感受性レジスト材料およびエネルギー感受性レジスト材料を使用したデバイスの製造方法 |
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Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003040930A (ja) * | 2001-07-27 | 2003-02-13 | Jsr Corp | 環状オレフィン付加重合体の製造方法 |
| JP2003040929A (ja) * | 2001-07-27 | 2003-02-13 | Jsr Corp | 環状オレフィン付加重合体の製造方法 |
| JP2005171234A (ja) * | 2003-11-18 | 2005-06-30 | Jsr Corp | 新規な（共）重合体およびその製造方法並びにカルボキシル基含有（共）重合体の製造方法 |
| JP2007534796A (ja) * | 2004-02-23 | 2007-11-29 | ランクセス・インコーポレーテッド | 低分子量ニトリルゴムの調製方法 |
| JP2006111733A (ja) * | 2004-10-14 | 2006-04-27 | Tokyo Ohka Kogyo Co Ltd | 高分子化合物、ポジ型レジスト組成物およびレジストパターン形成方法 |
| WO2006064814A1 (ja) * | 2004-12-15 | 2006-06-22 | Nihon University | ノルボルネン系付加（共）重合体の製造方法 |
| JP5411407B2 (ja) * | 2004-12-15 | 2014-02-12 | 学校法人日本大学 | ノルボルネン系付加（共）重合体の製造方法 |
| JP2009242797A (ja) * | 2005-02-22 | 2009-10-22 | Promerus Llc | ノルボルネン系ポリマー、その組成物、及び該組成物を使用するリソグラフィ法 |
| JP2008536956A (ja) * | 2005-02-22 | 2008-09-11 | プロメラス， エルエルシー | ノルボルネン系ポリマー、その組成物、及び該組成物を使用するリソグラフィ法 |
| JP2007091634A (ja) * | 2005-09-28 | 2007-04-12 | Central Glass Co Ltd | α−置換アクリル酸ノルボルナニル類の製造方法 |
| JP2008050342A (ja) * | 2006-07-26 | 2008-03-06 | Central Glass Co Ltd | Ｎ−（ビシクロ［２，２，１］ヘプト−５−エン−２−イルメチル）−１，１，１−トリフルオロメタンスルホンアミドの製造方法 |
| WO2008099725A1 (ja) * | 2007-02-15 | 2008-08-21 | Tokyo Ohka Kogyo Co., Ltd. | 高分子化合物、レジスト組成物及びレジストパターン形成方法 |
| US8021824B2 (en) | 2007-02-15 | 2011-09-20 | Tokyo Ohka Kogyo Co., Ltd. | Polymer compound, resist composition and method of forming resist pattern |
| JP2009096767A (ja) * | 2007-10-18 | 2009-05-07 | Kuraray Co Ltd | スルホニルハライド誘導体の製造方法 |
| JP2010083873A (ja) * | 2008-09-02 | 2010-04-15 | Kuraray Co Ltd | スルトン誘導体の製造方法 |
| JP2010132664A (ja) * | 2009-12-28 | 2010-06-17 | Tokyo Ohka Kogyo Co Ltd | 新規な化合物、及びその製造方法、並びに高分子化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1157058A1 (en) | 2001-11-28 |
| KR20010089637A (ko) | 2001-10-06 |
| ATE243719T1 (de) | 2003-07-15 |
| US6235849B1 (en) | 2001-05-22 |
| DE60003529D1 (de) | 2003-07-31 |
| KR100687963B1 (ko) | 2007-02-27 |
| AU2757300A (en) | 2000-08-25 |
| DE60003529T2 (de) | 2004-04-29 |
| EP1157058B1 (en) | 2003-06-25 |
| WO2000046267A1 (en) | 2000-08-10 |
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