JP4928495B2 - 有機テルル化合物、その製造方法、リビングラジカル重合開始剤、それを用いるポリマーの製造法及びポリマー - Google Patents
有機テルル化合物、その製造方法、リビングラジカル重合開始剤、それを用いるポリマーの製造法及びポリマー Download PDFInfo
- Publication number
- JP4928495B2 JP4928495B2 JP2008121333A JP2008121333A JP4928495B2 JP 4928495 B2 JP4928495 B2 JP 4928495B2 JP 2008121333 A JP2008121333 A JP 2008121333A JP 2008121333 A JP2008121333 A JP 2008121333A JP 4928495 B2 JP4928495 B2 JP 4928495B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- mmol
- methylterranyl
- benzene
- ethyl
- 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
- 150000003498 tellurium compounds Chemical class 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 18
- 229920000642 polymer Polymers 0.000 title description 60
- 238000010526 radical polymerization reaction Methods 0.000 title description 37
- 239000007870 radical polymerization initiator Substances 0.000 title description 27
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 27
- 229910052714 tellurium Inorganic materials 0.000 claims description 24
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 229910052751 metal Inorganic materials 0.000 claims description 18
- 239000002184 metal Substances 0.000 claims description 18
- 229910052783 alkali metal Inorganic materials 0.000 claims description 17
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 15
- 150000001340 alkali metals Chemical class 0.000 claims description 15
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 15
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 207
- 238000006243 chemical reaction Methods 0.000 description 63
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 53
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- 238000005160 1H NMR spectroscopy Methods 0.000 description 29
- 239000000178 monomer Substances 0.000 description 29
- 238000005227 gel permeation chromatography Methods 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 21
- -1 n-octyl group Chemical group 0.000 description 21
- 239000004793 Polystyrene Substances 0.000 description 20
- 238000004458 analytical method Methods 0.000 description 20
- 229920002223 polystyrene Polymers 0.000 description 20
- 150000003254 radicals Chemical class 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 14
- 229920002554 vinyl polymer Polymers 0.000 description 14
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- 125000003107 substituted aryl group Chemical group 0.000 description 12
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000009826 distribution Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 8
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 7
- GHGVPCNHGZIJRN-UHFFFAOYSA-N 2-ethenyl-1-methylpyrrole Chemical compound CN1C=CC=C1C=C GHGVPCNHGZIJRN-UHFFFAOYSA-N 0.000 description 7
- ORNUPNRNNSVZTC-UHFFFAOYSA-N 2-vinylthiophene Chemical compound C=CC1=CC=CS1 ORNUPNRNNSVZTC-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- YCIGYTFKOXGYTA-UHFFFAOYSA-N 4-(3-cyanopropyldiazenyl)butanenitrile Chemical compound N#CCCCN=NCCCC#N YCIGYTFKOXGYTA-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 229920000428 triblock copolymer Polymers 0.000 description 5
- CRRUGYDDEMGVDY-UHFFFAOYSA-N 1-bromoethylbenzene Chemical compound CC(Br)C1=CC=CC=C1 CRRUGYDDEMGVDY-UHFFFAOYSA-N 0.000 description 4
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 229920001400 block copolymer Polymers 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- JYQIUMNHRQYUHC-UHFFFAOYSA-N 1-(1-bromoethyl)-4-chlorobenzene Chemical compound CC(Br)C1=CC=C(Cl)C=C1 JYQIUMNHRQYUHC-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 229910052805 deuterium Inorganic materials 0.000 description 3
- 229920000359 diblock copolymer Polymers 0.000 description 3
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000001226 reprecipitation Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 3
- MVOSNPUNXINWAD-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanol Chemical compound CC(O)C1=CC=C(Cl)C=C1 MVOSNPUNXINWAD-UHFFFAOYSA-N 0.000 description 2
- ZXCXIXDKAILICW-UHFFFAOYSA-N 1-(benzenesulfonyl)propyl prop-2-enoate Chemical compound C=CC(=O)OC(CC)S(=O)(=O)C1=CC=CC=C1 ZXCXIXDKAILICW-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- PYNYHMRMZOGVML-UHFFFAOYSA-N 2-bromopropanenitrile Chemical compound CC(Br)C#N PYNYHMRMZOGVML-UHFFFAOYSA-N 0.000 description 2
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 2
- SUYCKBOGLWSODS-UHFFFAOYSA-N 2-sulfonylpropanenitrile Chemical compound N#CC(C)=S(=O)=O SUYCKBOGLWSODS-UHFFFAOYSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 2
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- UXOFRFPVWFJROK-UHFFFAOYSA-N (2-ethenylphenyl)methanol Chemical compound OCC1=CC=CC=C1C=C UXOFRFPVWFJROK-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- QVLAWKAXOMEXPM-DICFDUPASA-N 1,1,1,2-tetrachloro-2,2-dideuterioethane Chemical compound [2H]C([2H])(Cl)C(Cl)(Cl)Cl QVLAWKAXOMEXPM-DICFDUPASA-N 0.000 description 1
- VWPMBVBOSDEYQU-UHFFFAOYSA-N 1-(1-bromoethyl)-4-(trifluoromethyl)benzene Chemical compound CC(Br)C1=CC=C(C(F)(F)F)C=C1 VWPMBVBOSDEYQU-UHFFFAOYSA-N 0.000 description 1
- KZYDZNLNJFSFKL-UHFFFAOYSA-N 1-(1-bromoethyl)-4-methoxybenzene Chemical compound COC1=CC=C(C(C)Br)C=C1 KZYDZNLNJFSFKL-UHFFFAOYSA-N 0.000 description 1
- LLTKPPRBFXTUKH-UHFFFAOYSA-N 1-(1-bromoethyl)-4-nitrobenzene Chemical compound CC(Br)C1=CC=C([N+]([O-])=O)C=C1 LLTKPPRBFXTUKH-UHFFFAOYSA-N 0.000 description 1
- CKKMRMKMZIDSDS-UHFFFAOYSA-N 1-(1-chloroethyl)-4-(trifluoromethyl)benzene Chemical compound CC(Cl)C1=CC=C(C(F)(F)F)C=C1 CKKMRMKMZIDSDS-UHFFFAOYSA-N 0.000 description 1
- LATFGMPDXQAUFT-UHFFFAOYSA-N 1-(1-chloroethyl)-4-nitrobenzene Chemical compound CC(Cl)C1=CC=C([N+]([O-])=O)C=C1 LATFGMPDXQAUFT-UHFFFAOYSA-N 0.000 description 1
- YYGMKFDVMVLTPQ-UHFFFAOYSA-N 1-(2-bromopropan-2-yl)-4-(trifluoromethyl)benzene Chemical compound CC(C)(Br)C1=CC=C(C(F)(F)F)C=C1 YYGMKFDVMVLTPQ-UHFFFAOYSA-N 0.000 description 1
- MDWSMBKRQRJNKR-UHFFFAOYSA-N 1-(2-bromopropan-2-yl)-4-chlorobenzene Chemical compound CC(C)(Br)C1=CC=C(Cl)C=C1 MDWSMBKRQRJNKR-UHFFFAOYSA-N 0.000 description 1
- UXESGYJMLFCJTM-UHFFFAOYSA-N 1-(2-bromopropan-2-yl)-4-methoxybenzene Chemical compound COC1=CC=C(C(C)(C)Br)C=C1 UXESGYJMLFCJTM-UHFFFAOYSA-N 0.000 description 1
- YHQZKFLXFSZILC-UHFFFAOYSA-N 1-(2-bromopropan-2-yl)-4-nitrobenzene Chemical compound CC(C)(Br)C1=CC=C([N+]([O-])=O)C=C1 YHQZKFLXFSZILC-UHFFFAOYSA-N 0.000 description 1
- ZFJADWUTIAZSSE-UHFFFAOYSA-N 1-(2-chloropropan-2-yl)-4-(trifluoromethyl)benzene Chemical compound CC(C)(Cl)C1=CC=C(C(F)(F)F)C=C1 ZFJADWUTIAZSSE-UHFFFAOYSA-N 0.000 description 1
- UNBCDUHLWPJWNW-UHFFFAOYSA-N 1-(2-chloropropan-2-yl)-4-methoxybenzene Chemical compound COC1=CC=C(C(C)(C)Cl)C=C1 UNBCDUHLWPJWNW-UHFFFAOYSA-N 0.000 description 1
- WZDVAXOJQKDXMD-UHFFFAOYSA-N 1-(2-chloropropan-2-yl)-4-nitrobenzene Chemical compound CC(C)(Cl)C1=CC=C([N+]([O-])=O)C=C1 WZDVAXOJQKDXMD-UHFFFAOYSA-N 0.000 description 1
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 1
- MCHDHQVROPEJJT-UHFFFAOYSA-N 1-(chloromethyl)-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(CCl)C=C1 MCHDHQVROPEJJT-UHFFFAOYSA-N 0.000 description 1
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 1
- OUKQTRFCDKSEPL-UHFFFAOYSA-N 1-Methyl-2-pyrrolecarboxaldehyde Chemical compound CN1C=CC=C1C=O OUKQTRFCDKSEPL-UHFFFAOYSA-N 0.000 description 1
- YQPAQEUKZZILRA-UHFFFAOYSA-N 1-[4-(1-bromoethyl)phenyl]ethanone Chemical compound CC(Br)C1=CC=C(C(C)=O)C=C1 YQPAQEUKZZILRA-UHFFFAOYSA-N 0.000 description 1
- BVKOZBOQDGCORU-UHFFFAOYSA-N 1-[4-(1-chloroethyl)phenyl]ethanone Chemical compound CC(Cl)C1=CC=C(C(C)=O)C=C1 BVKOZBOQDGCORU-UHFFFAOYSA-N 0.000 description 1
- RSWDNZBWBLCDHI-UHFFFAOYSA-N 1-[4-(2-chloropropan-2-yl)phenyl]ethanone Chemical compound CC(=O)C1=CC=C(C(C)(C)Cl)C=C1 RSWDNZBWBLCDHI-UHFFFAOYSA-N 0.000 description 1
- GAECNRSTNDHUBE-UHFFFAOYSA-N 1-[4-(chloromethyl)phenyl]ethanone Chemical compound CC(=O)C1=CC=C(CCl)C=C1 GAECNRSTNDHUBE-UHFFFAOYSA-N 0.000 description 1
- NOCHRVHWICTPLG-UHFFFAOYSA-N 1-chloro-4-(1-chloroethyl)benzene Chemical compound CC(Cl)C1=CC=C(Cl)C=C1 NOCHRVHWICTPLG-UHFFFAOYSA-N 0.000 description 1
- BXZHFMJLWRWYBV-UHFFFAOYSA-N 1-chloro-4-(2-chloropropan-2-yl)benzene Chemical compound CC(C)(Cl)C1=CC=C(Cl)C=C1 BXZHFMJLWRWYBV-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- GTLWADFFABIGAE-UHFFFAOYSA-N 1-chloroethylbenzene Chemical compound CC(Cl)C1=CC=CC=C1 GTLWADFFABIGAE-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- OZGSEIVTQLXWRO-UHFFFAOYSA-N 2,4,6-trichlorobenzoyl chloride Chemical compound ClC(=O)C1=C(Cl)C=C(Cl)C=C1Cl OZGSEIVTQLXWRO-UHFFFAOYSA-N 0.000 description 1
- OMNYXCUDBQKCMU-UHFFFAOYSA-N 2,4-dichloro-1-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C(Cl)=C1 OMNYXCUDBQKCMU-UHFFFAOYSA-N 0.000 description 1
- CCRIVINSZBIKQU-UHFFFAOYSA-N 2-(1-bromoethyl)-5-sulfonylcyclohexa-1,3-diene Chemical compound CC(Br)C1=CCC(=S(=O)=O)C=C1 CCRIVINSZBIKQU-UHFFFAOYSA-N 0.000 description 1
- NXZNOPMZKPTBHC-UHFFFAOYSA-N 2-(1-bromoethyl)pyridine Chemical compound CC(Br)C1=CC=CC=N1 NXZNOPMZKPTBHC-UHFFFAOYSA-N 0.000 description 1
- UHKJOOFABPOOJZ-UHFFFAOYSA-N 2-(1-chloroethyl)-5-sulfonylcyclohexa-1,3-diene Chemical compound CC(Cl)C1=CCC(=S(=O)=O)C=C1 UHKJOOFABPOOJZ-UHFFFAOYSA-N 0.000 description 1
- ZHBVIIQZRLPHGH-UHFFFAOYSA-N 2-(1-chloroethyl)pyridine Chemical compound CC(Cl)C1=CC=CC=N1 ZHBVIIQZRLPHGH-UHFFFAOYSA-N 0.000 description 1
- QNUYIYMWUNZCBB-UHFFFAOYSA-N 2-(2-bromopropan-2-yl)-5-sulfonylcyclohexa-1,3-diene Chemical compound CC(C)(Br)C1=CCC(=S(=O)=O)C=C1 QNUYIYMWUNZCBB-UHFFFAOYSA-N 0.000 description 1
- NMGHANOTFGYPMM-UHFFFAOYSA-N 2-(2-bromopropyl)pyridine Chemical compound CC(Br)CC1=CC=CC=N1 NMGHANOTFGYPMM-UHFFFAOYSA-N 0.000 description 1
- CFIGGLOCSXZMDF-UHFFFAOYSA-N 2-(2-chloropropan-2-yl)-5-sulfonylcyclohexa-1,3-diene Chemical compound CC(C)(Cl)C1=CCC(=S(=O)=O)C=C1 CFIGGLOCSXZMDF-UHFFFAOYSA-N 0.000 description 1
- FNJNWLJFGOJWDT-UHFFFAOYSA-N 2-(2-chloropropyl)pyridine Chemical compound CC(Cl)CC1=CC=CC=N1 FNJNWLJFGOJWDT-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- OFPWMRMIFDHXFE-UHFFFAOYSA-N 2-(bromomethyl)pyridine Chemical compound BrCC1=CC=CC=N1 OFPWMRMIFDHXFE-UHFFFAOYSA-N 0.000 description 1
- IYJDJLAQYFJJJB-UHFFFAOYSA-N 2-(chloromethyl)-5-sulfonylcyclohexa-1,3-diene Chemical compound ClCC1=CCC(=S(=O)=O)C=C1 IYJDJLAQYFJJJB-UHFFFAOYSA-N 0.000 description 1
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 1
- XDSDCTDECRVDTB-UHFFFAOYSA-N 2-bromo-2-methylpropanenitrile Chemical compound CC(C)(Br)C#N XDSDCTDECRVDTB-UHFFFAOYSA-N 0.000 description 1
- REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 1
- WSFSJXBURLJOFD-UHFFFAOYSA-N 2-bromopropan-2-ylbenzene Chemical compound CC(C)(Br)C1=CC=CC=C1 WSFSJXBURLJOFD-UHFFFAOYSA-N 0.000 description 1
- RXDYOLRABMJTEF-UHFFFAOYSA-N 2-chloro-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Cl)C(=O)C1=CC=CC=C1 RXDYOLRABMJTEF-UHFFFAOYSA-N 0.000 description 1
- AMAFFZUDKROYAJ-UHFFFAOYSA-N 2-chloro-2-methylpropanenitrile Chemical compound CC(C)(Cl)C#N AMAFFZUDKROYAJ-UHFFFAOYSA-N 0.000 description 1
- KPJKMUJJFXZGAX-UHFFFAOYSA-N 2-chloropropan-2-ylbenzene Chemical compound CC(C)(Cl)C1=CC=CC=C1 KPJKMUJJFXZGAX-UHFFFAOYSA-N 0.000 description 1
- JNAYPRPPXRWGQO-UHFFFAOYSA-N 2-chloropropanenitrile Chemical compound CC(Cl)C#N JNAYPRPPXRWGQO-UHFFFAOYSA-N 0.000 description 1
- ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- CWNPOQFCIIFQDM-UHFFFAOYSA-N 3-nitrobenzyl alcohol Chemical compound OCC1=CC=CC([N+]([O-])=O)=C1 CWNPOQFCIIFQDM-UHFFFAOYSA-N 0.000 description 1
- DHLBXOLRKWLEIF-UHFFFAOYSA-N 4-(1-bromoethyl)aniline Chemical compound CC(Br)C1=CC=C(N)C=C1 DHLBXOLRKWLEIF-UHFFFAOYSA-N 0.000 description 1
- ABYAXYCLTMBACL-UHFFFAOYSA-N 4-(1-bromoethyl)benzonitrile Chemical compound CC(Br)C1=CC=C(C#N)C=C1 ABYAXYCLTMBACL-UHFFFAOYSA-N 0.000 description 1
- JSYMQYVQRDGSRN-UHFFFAOYSA-N 4-(1-bromoethyl)phenol Chemical compound CC(Br)C1=CC=C(O)C=C1 JSYMQYVQRDGSRN-UHFFFAOYSA-N 0.000 description 1
- GZVQLYYEFBBJBC-UHFFFAOYSA-N 4-(1-chloroethyl)aniline Chemical compound CC(Cl)C1=CC=C(N)C=C1 GZVQLYYEFBBJBC-UHFFFAOYSA-N 0.000 description 1
- PNLPKTZRNPNYMJ-UHFFFAOYSA-N 4-(1-chloroethyl)benzonitrile Chemical compound CC(Cl)C1=CC=C(C#N)C=C1 PNLPKTZRNPNYMJ-UHFFFAOYSA-N 0.000 description 1
- AMZHYIJTAPRTLG-UHFFFAOYSA-N 4-(1-chloroethyl)phenol Chemical compound CC(Cl)C1=CC=C(O)C=C1 AMZHYIJTAPRTLG-UHFFFAOYSA-N 0.000 description 1
- ROHKWWBGSPEMAX-UHFFFAOYSA-N 4-(2-bromopropan-2-yl)aniline Chemical compound CC(C)(Br)C1=CC=C(N)C=C1 ROHKWWBGSPEMAX-UHFFFAOYSA-N 0.000 description 1
- XRNAOFNXOYBYHS-UHFFFAOYSA-N 4-(2-bromopropan-2-yl)benzonitrile Chemical compound CC(C)(Br)C1=CC=C(C#N)C=C1 XRNAOFNXOYBYHS-UHFFFAOYSA-N 0.000 description 1
- IIJRUNJPSXZBET-UHFFFAOYSA-N 4-(2-bromopropan-2-yl)phenol Chemical compound CC(C)(Br)C1=CC=C(O)C=C1 IIJRUNJPSXZBET-UHFFFAOYSA-N 0.000 description 1
- MHEOFRJQYGSSTE-UHFFFAOYSA-N 4-(2-chloropropan-2-yl)phenol Chemical compound CC(C)(Cl)C1=CC=C(O)C=C1 MHEOFRJQYGSSTE-UHFFFAOYSA-N 0.000 description 1
- FOMVMXBARQUECW-UHFFFAOYSA-N 4-(chloromethyl)aniline Chemical compound NC1=CC=C(CCl)C=C1 FOMVMXBARQUECW-UHFFFAOYSA-N 0.000 description 1
- LOQLDQJTSMKBJU-UHFFFAOYSA-N 4-(chloromethyl)benzonitrile Chemical compound ClCC1=CC=C(C#N)C=C1 LOQLDQJTSMKBJU-UHFFFAOYSA-N 0.000 description 1
- SSIMHHUMYMHNID-UHFFFAOYSA-N 4-(chloromethyl)phenol Chemical compound OC1=CC=C(CCl)C=C1 SSIMHHUMYMHNID-UHFFFAOYSA-N 0.000 description 1
- MRENSFROWALQNU-UHFFFAOYSA-N 4-pyren-1-ylbutan-1-ol Chemical compound C1=C2C(CCCCO)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 MRENSFROWALQNU-UHFFFAOYSA-N 0.000 description 1
- OAAGDVLVOKMRCQ-UHFFFAOYSA-N 5-piperidin-4-yl-3-pyridin-4-yl-1,2,4-oxadiazole Chemical compound C1CNCCC1C1=NC(C=2C=CN=CC=2)=NO1 OAAGDVLVOKMRCQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 108700015862 A-B-A triblock copolymer Proteins 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- VHNLEIBYURPBRX-UHFFFAOYSA-N BrC(C)C1=CC=C(C=C1)C(=O)C1=CC=CC=C1.ClC(C)C1=CC=C(C=C1)C(=O)C1=CC=CC=C1 Chemical compound BrC(C)C1=CC=C(C=C1)C(=O)C1=CC=CC=C1.ClC(C)C1=CC=C(C=C1)C(=O)C1=CC=CC=C1 VHNLEIBYURPBRX-UHFFFAOYSA-N 0.000 description 1
- BSMUSCSUILYGIF-UHFFFAOYSA-N C=CC1=CC=C(C=C1)S(=O)(=O)O.C(=C)C1=C(C=CC=C1)C=C Chemical compound C=CC1=CC=C(C=C1)S(=O)(=O)O.C(=C)C1=C(C=CC=C1)C=C BSMUSCSUILYGIF-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- SMIBLOOMRPIHDO-UHFFFAOYSA-N [4-(2-bromopropan-2-yl)phenyl]-phenylmethanone Chemical compound C1=CC(C(C)(Br)C)=CC=C1C(=O)C1=CC=CC=C1 SMIBLOOMRPIHDO-UHFFFAOYSA-N 0.000 description 1
- SFRLXSCEFIQIJI-UHFFFAOYSA-N [4-(2-chloropropan-2-yl)phenyl]-phenylmethanone Chemical compound C1=CC(C(C)(Cl)C)=CC=C1C(=O)C1=CC=CC=C1 SFRLXSCEFIQIJI-UHFFFAOYSA-N 0.000 description 1
- SXTULILTUYKOHV-UHFFFAOYSA-N [Li]C1=CC=C(Cl)C=C1 Chemical compound [Li]C1=CC=C(Cl)C=C1 SXTULILTUYKOHV-UHFFFAOYSA-N 0.000 description 1
- ODEWMQYJJFFIMH-UHFFFAOYSA-N [Li]c1ccc(cc1)[N+]([O-])=O Chemical compound [Li]c1ccc(cc1)[N+]([O-])=O ODEWMQYJJFFIMH-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- NZEWVJWONYBVFL-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;styrene Chemical compound COC(=O)C(C)=C.C=CC1=CC=CC=C1.CCCCOC(=O)C=C NZEWVJWONYBVFL-UHFFFAOYSA-N 0.000 description 1
- TUZBYYLVVXPEMA-UHFFFAOYSA-N butyl prop-2-enoate;styrene Chemical compound C=CC1=CC=CC=C1.CCCCOC(=O)C=C TUZBYYLVVXPEMA-UHFFFAOYSA-N 0.000 description 1
- XBWAWBVWKGCMOG-UHFFFAOYSA-N butyl prop-2-enoate;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1.CCCCOC(=O)C=C XBWAWBVWKGCMOG-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- OLYPZOMHOKXSGU-UHFFFAOYSA-N cyclododecyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCCCCCCCC1 OLYPZOMHOKXSGU-UHFFFAOYSA-N 0.000 description 1
- WJYHCYBNUJVCEH-UHFFFAOYSA-N cyclohexane;ethoxyethane Chemical compound CCOCC.C1CCCCC1 WJYHCYBNUJVCEH-UHFFFAOYSA-N 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 150000001975 deuterium Chemical group 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 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 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- MTCMFVTVXAOHNQ-UHFFFAOYSA-N ethyl 2-(bromomethyl)prop-2-enoate Chemical compound CCOC(=O)C(=C)CBr MTCMFVTVXAOHNQ-UHFFFAOYSA-N 0.000 description 1
- ALHOFXQMBUWICK-UHFFFAOYSA-N ethyl 2-bromo-2-methylbutanoate Chemical compound CCOC(=O)C(C)(Br)CC ALHOFXQMBUWICK-UHFFFAOYSA-N 0.000 description 1
- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 1
- AHKRUABVICCJAM-UHFFFAOYSA-N ethyl 2-chloro-2-methylbutanoate Chemical compound CCOC(=O)C(C)(Cl)CC AHKRUABVICCJAM-UHFFFAOYSA-N 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- GVLUZLIABKNMAY-UHFFFAOYSA-N lithium;methoxybenzene Chemical compound [Li+].COC1=CC=[C-]C=C1 GVLUZLIABKNMAY-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229960003505 mequinol Drugs 0.000 description 1
- PQUSVJVVRXWKDG-UHFFFAOYSA-N methyl 2-bromo-2-methylpropanoate Chemical compound COC(=O)C(C)(C)Br PQUSVJVVRXWKDG-UHFFFAOYSA-N 0.000 description 1
- GJWBUVKJZQLZNB-UHFFFAOYSA-N methyl 2-chloro-2-methylpropanoate Chemical compound COC(=O)C(C)(C)Cl GJWBUVKJZQLZNB-UHFFFAOYSA-N 0.000 description 1
- JLEJCNOTNLZCHQ-UHFFFAOYSA-N methyl 2-chloropropanoate Chemical compound COC(=O)C(C)Cl JLEJCNOTNLZCHQ-UHFFFAOYSA-N 0.000 description 1
- IXZOUWPYWNKWCX-UHFFFAOYSA-N methyl 4-(1-bromoethyl)benzoate Chemical compound COC(=O)C1=CC=C(C(C)Br)C=C1 IXZOUWPYWNKWCX-UHFFFAOYSA-N 0.000 description 1
- JJSVUVWPLHBCGT-UHFFFAOYSA-N methyl 4-(1-chloroethyl)benzoate Chemical compound COC(=O)C1=CC=C(C(C)Cl)C=C1 JJSVUVWPLHBCGT-UHFFFAOYSA-N 0.000 description 1
- MQAGANABMUWPDX-UHFFFAOYSA-N methyl 4-(2-bromopropan-2-yl)benzoate Chemical compound COC(=O)C1=CC=C(C(C)(C)Br)C=C1 MQAGANABMUWPDX-UHFFFAOYSA-N 0.000 description 1
- SATDLKYRVXFXRE-UHFFFAOYSA-N methyl 4-(chloromethyl)benzoate Chemical compound COC(=O)C1=CC=C(CCl)C=C1 SATDLKYRVXFXRE-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 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
- 239000012452 mother liquor Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 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 description 1
- KGCNHWXDPDPSBV-UHFFFAOYSA-N p-nitrobenzyl chloride Chemical compound [O-][N+](=O)C1=CC=C(CCl)C=C1 KGCNHWXDPDPSBV-UHFFFAOYSA-N 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- JBDCYYQRIFPFPT-UHFFFAOYSA-N phenyl 4-(1-bromoethyl)benzoate Chemical compound C1=CC(C(Br)C)=CC=C1C(=O)OC1=CC=CC=C1 JBDCYYQRIFPFPT-UHFFFAOYSA-N 0.000 description 1
- LLCSYPLLEPFPTL-UHFFFAOYSA-N phenyl 4-(1-chloroethyl)benzoate Chemical compound C1=CC(C(Cl)C)=CC=C1C(=O)OC1=CC=CC=C1 LLCSYPLLEPFPTL-UHFFFAOYSA-N 0.000 description 1
- ALWZOEVLPYSATD-UHFFFAOYSA-N phenyl 4-(2-chloropropan-2-yl)benzoate Chemical compound ClC(C)(C)C1=CC=C(C=C1)C(=O)OC1=CC=CC=C1 ALWZOEVLPYSATD-UHFFFAOYSA-N 0.000 description 1
- BONLOIKKTQFCBK-UHFFFAOYSA-N phenyl 4-(chloromethyl)benzoate Chemical compound C1=CC(CCl)=CC=C1C(=O)OC1=CC=CC=C1 BONLOIKKTQFCBK-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerization Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008121333A JP4928495B2 (ja) | 2008-05-07 | 2008-05-07 | 有機テルル化合物、その製造方法、リビングラジカル重合開始剤、それを用いるポリマーの製造法及びポリマー |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008121333A JP4928495B2 (ja) | 2008-05-07 | 2008-05-07 | 有機テルル化合物、その製造方法、リビングラジカル重合開始剤、それを用いるポリマーの製造法及びポリマー |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004527297A Division JP4464821B2 (ja) | 2002-08-06 | 2002-08-06 | 有機テルル化合物、その製造方法、リビングラジカル重合開始剤、それを用いるポリマーの製造方法及びポリマー |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008247919A JP2008247919A (ja) | 2008-10-16 |
| JP2008247919A5 JP2008247919A5 (enExample) | 2010-01-14 |
| JP4928495B2 true JP4928495B2 (ja) | 2012-05-09 |
Family
ID=39973276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008121333A Expired - Lifetime JP4928495B2 (ja) | 2008-05-07 | 2008-05-07 | 有機テルル化合物、その製造方法、リビングラジカル重合開始剤、それを用いるポリマーの製造法及びポリマー |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4928495B2 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5172494B2 (ja) | 2008-06-23 | 2013-03-27 | 東京応化工業株式会社 | 液浸露光用レジスト組成物、レジストパターン形成方法、含フッ素高分子化合物 |
| JP5292133B2 (ja) | 2009-03-09 | 2013-09-18 | 東京応化工業株式会社 | ポジ型レジスト組成物及びレジストパターン形成方法 |
| JP5346627B2 (ja) | 2009-03-10 | 2013-11-20 | 東京応化工業株式会社 | ポジ型レジスト組成物及びレジストパターン形成方法 |
| JP5568258B2 (ja) | 2009-07-03 | 2014-08-06 | 東京応化工業株式会社 | ポジ型レジスト組成物およびそれを用いたレジストパターン形成方法、並びに含フッ素高分子化合物 |
| JP5470053B2 (ja) | 2010-01-05 | 2014-04-16 | 東京応化工業株式会社 | ポジ型レジスト組成物、レジストパターン形成方法 |
| US11427538B2 (en) | 2017-04-28 | 2022-08-30 | Kyoto University | Organic tellurium compound, method for producing same, living radical polymerization initiator, method for producing vinyl polymer, and vinyl polymer |
-
2008
- 2008-05-07 JP JP2008121333A patent/JP4928495B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008247919A (ja) | 2008-10-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4464821B2 (ja) | 有機テルル化合物、その製造方法、リビングラジカル重合開始剤、それを用いるポリマーの製造方法及びポリマー | |
| JP3839829B2 (ja) | リビングラジカルポリマーの製造方法及びポリマー | |
| JP3845109B2 (ja) | リビングラジカルポリマーの製造方法及びポリマー | |
| JP3845108B2 (ja) | リビングラジカルポリマーの製造方法及びポリマー | |
| JP4928495B2 (ja) | 有機テルル化合物、その製造方法、リビングラジカル重合開始剤、それを用いるポリマーの製造法及びポリマー | |
| JP2006299278A (ja) | リビングラジカルポリマーの製造方法 | |
| JP4107996B2 (ja) | リビングラジカルポリマーの製造方法及びポリマー | |
| KR100708959B1 (ko) | 유기 텔루르화합물, 그의 제조방법, 리빙 라디칼중합개시제, 그것을 사용하는 폴리머의 제조방법 및 폴리머 | |
| RU2301809C2 (ru) | Теллурорганические соединения, способ их получения, инициаторы "живой" полимеризации, способы получения полимеров, полимеры, блок-сополимеры | |
| KR20050047087A (ko) | 유기 텔루르화합물, 그의 제조방법, 리빙 라디칼중합개시제, 그것을 사용하는 폴리머의 제조방법 및 폴리머 | |
| JP2007302737A (ja) | リビングラジカルポリマーの製造方法 | |
| KR100589035B1 (ko) | 리빙 라디칼 폴리머의 제조방법 및 폴리머 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A712 Effective date: 20090821 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20091118 |
|
| RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20100701 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20110608 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110614 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110721 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20120124 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120210 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150217 Year of fee payment: 3 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 4928495 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |