JP4895416B2 - 制御されたラジカル重合方法における調節剤としての複素環式アルコキシアミン - Google Patents
制御されたラジカル重合方法における調節剤としての複素環式アルコキシアミン Download PDFInfo
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- JP4895416B2 JP4895416B2 JP29369799A JP29369799A JP4895416B2 JP 4895416 B2 JP4895416 B2 JP 4895416B2 JP 29369799 A JP29369799 A JP 29369799A JP 29369799 A JP29369799 A JP 29369799A JP 4895416 B2 JP4895416 B2 JP 4895416B2
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- 238000010526 radical polymerization reaction Methods 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 382
- 125000004432 carbon atom Chemical group C* 0.000 claims description 323
- 239000000178 monomer Substances 0.000 claims description 181
- 125000000217 alkyl group Chemical group 0.000 claims description 158
- 238000006116 polymerization reaction Methods 0.000 claims description 123
- 239000000203 mixture Substances 0.000 claims description 94
- -1 glycidyloxy group Chemical group 0.000 claims description 49
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 49
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 33
- 125000003342 alkenyl group Chemical group 0.000 claims description 30
- 125000000304 alkynyl group Chemical group 0.000 claims description 30
- 229920000642 polymer Polymers 0.000 claims description 29
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 27
- 150000003254 radicals Chemical class 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 14
- 239000003999 initiator Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 138
- 229910052757 nitrogen Inorganic materials 0.000 description 102
- 239000000243 solution Substances 0.000 description 99
- 229910052739 hydrogen Inorganic materials 0.000 description 98
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 82
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 78
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 78
- 238000005227 gel permeation chromatography Methods 0.000 description 71
- 239000007788 liquid Substances 0.000 description 71
- 239000012300 argon atmosphere Substances 0.000 description 67
- 238000000921 elemental analysis Methods 0.000 description 61
- 238000005259 measurement Methods 0.000 description 60
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 54
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
- 238000005160 1H NMR spectroscopy Methods 0.000 description 46
- 238000002844 melting Methods 0.000 description 46
- 230000008018 melting Effects 0.000 description 46
- 239000012230 colorless oil Substances 0.000 description 35
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical group CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 34
- 239000003921 oil Substances 0.000 description 30
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 235000019439 ethyl acetate Nutrition 0.000 description 28
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 25
- 239000013078 crystal Substances 0.000 description 25
- CHWVDGYLKPLBES-UHFFFAOYSA-N 5-(2-methoxyphenyl)-2-furoic acid Chemical compound COC1=CC=CC=C1C1=CC=C(C(O)=O)O1 CHWVDGYLKPLBES-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000009826 distribution Methods 0.000 description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
- 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 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 12
- 229920001400 block copolymer Polymers 0.000 description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 0 CN(C(*)(N(C1(*)*)O*)I)C1=O Chemical compound CN(C(*)(N(C1(*)*)O*)I)C1=O 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- VUEVTMMLZSUWIL-UHFFFAOYSA-N 1-butyl-3-ethyl-3,5,5,7-tetramethyl-1,4-diazepan-2-one Chemical compound CCCCN1C(C)CC(C)(C)NC(C)(CC)C1=O VUEVTMMLZSUWIL-UHFFFAOYSA-N 0.000 description 6
- GBBADHNSBOEAJD-UHFFFAOYSA-N 1-n-tert-butyl-2-ethylbutane-1,2-diamine Chemical compound CCC(N)(CC)CNC(C)(C)C GBBADHNSBOEAJD-UHFFFAOYSA-N 0.000 description 6
- VFIXFSTVCVVOML-UHFFFAOYSA-N 1-tert-butyl-3,3-diethyl-5,5-dimethyl-4-(1-phenylethoxy)piperazin-2-one Chemical compound CC1(C)CN(C(C)(C)C)C(=O)C(CC)(CC)N1OC(C)C1=CC=CC=C1 VFIXFSTVCVVOML-UHFFFAOYSA-N 0.000 description 6
- BIQOVFVAJAEPIR-UHFFFAOYSA-N 2-(2-ethyl-2,6,6-trimethyl-3-oxo-4-propan-2-ylpiperazin-1-yl)oxy-2-methylpropanenitrile Chemical compound CCC1(C)N(OC(C)(C)C#N)C(C)(C)CN(C(C)C)C1=O BIQOVFVAJAEPIR-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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- RLOSKMLOTKSUCJ-UHFFFAOYSA-N [5,5-diethyl-3-methyl-6-oxo-4-(1-phenylethoxy)morpholin-3-yl]methyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCC1(C)COC(=O)C(CC)(CC)N1OC(C)C1=CC=CC=C1 RLOSKMLOTKSUCJ-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000006184 cosolvent Substances 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- CGWSBVNBUPEXNY-UHFFFAOYSA-N (3,5,5-triethyl-6-oxomorpholin-3-yl)methyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCC1(CC)COC(=O)C(CC)(CC)N1 CGWSBVNBUPEXNY-UHFFFAOYSA-N 0.000 description 5
- BTSDTBBXGVOIDN-UHFFFAOYSA-N (5,5-diethyl-3-methyl-6-oxomorpholin-3-yl)methyl 2,2-dimethylpropanoate Chemical compound CCC1(CC)NC(C)(COC(=O)C(C)(C)C)COC1=O BTSDTBBXGVOIDN-UHFFFAOYSA-N 0.000 description 5
- KKWUZQSPIBAUDN-UHFFFAOYSA-N 1-tert-butyl-3,3,5-triethyl-5-methyl-4-(1-phenylethoxy)piperazin-2-one Chemical compound CCC1(C)CN(C(C)(C)C)C(=O)C(CC)(CC)N1OC(C)C1=CC=CC=C1 KKWUZQSPIBAUDN-UHFFFAOYSA-N 0.000 description 5
- DMOMLESTFQRBNY-UHFFFAOYSA-N 1-tert-butyl-5,5-diethyl-4-(1-phenylethoxy)-3,3-dipropylpiperazin-2-one Chemical compound CCC1(CC)CN(C(C)(C)C)C(=O)C(CCC)(CCC)N1OC(C)C1=CC=CC=C1 DMOMLESTFQRBNY-UHFFFAOYSA-N 0.000 description 5
- SKUZMLMCANXMFF-UHFFFAOYSA-N 2-[2,2-diethyl-6,6-dimethyl-3-oxo-4-(2,4,4-trimethylpentan-2-yl)piperazin-1-yl]oxy-2-methylpropanenitrile Chemical compound CCC1(CC)N(OC(C)(C)C#N)C(C)(C)CN(C(C)(C)CC(C)(C)C)C1=O SKUZMLMCANXMFF-UHFFFAOYSA-N 0.000 description 5
- BFYCCASBZGLDSH-UHFFFAOYSA-N 3,3,5,5-tetraethyl-4-(1-phenylethoxy)morpholin-2-one Chemical compound CCC1(CC)COC(=O)C(CC)(CC)N1OC(C)C1=CC=CC=C1 BFYCCASBZGLDSH-UHFFFAOYSA-N 0.000 description 5
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 5
- NYIPOHVLRWJXJY-UHFFFAOYSA-N 3-ethyl-3,5,5-trimethyl-1-propan-2-ylpiperazin-2-one Chemical compound CCC1(C)NC(C)(C)CN(C(C)C)C1=O NYIPOHVLRWJXJY-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229920000578 graft copolymer Polymers 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- XJYJNEVOBUSPSR-UHFFFAOYSA-N 1-benzyl-3,3-diethyl-5,5-dimethylpiperazin-2-one Chemical compound O=C1C(CC)(CC)NC(C)(C)CN1CC1=CC=CC=C1 XJYJNEVOBUSPSR-UHFFFAOYSA-N 0.000 description 4
- JFWQTDYJLXHVBB-UHFFFAOYSA-N 1-butyl-3,3,5,5,7-pentamethyl-4-(1-phenylethoxy)-1,4-diazepan-2-one Chemical compound CC1(C)C(=O)N(CCCC)C(C)CC(C)(C)N1OC(C)C1=CC=CC=C1 JFWQTDYJLXHVBB-UHFFFAOYSA-N 0.000 description 4
- ZQEKJXIMFCNSOI-UHFFFAOYSA-N 1-butyl-3-ethyl-3,5,5,7-tetramethyl-4-(1-phenylethoxy)-1,4-diazepan-2-one Chemical compound CCC1(C)C(=O)N(CCCC)C(C)CC(C)(C)N1OC(C)C1=CC=CC=C1 ZQEKJXIMFCNSOI-UHFFFAOYSA-N 0.000 description 4
- LHNWUKUFGXJJQG-UHFFFAOYSA-N 1-n-tert-butyl-2-methylpropane-1,2-diamine Chemical compound CC(C)(C)NCC(C)(C)N LHNWUKUFGXJJQG-UHFFFAOYSA-N 0.000 description 4
- GMDHSLALCRJDCT-UHFFFAOYSA-N 1-tert-butyl-3,3,5,5-tetraethyl-4-(1-phenylethoxy)piperazin-2-one Chemical compound CCC1(CC)CN(C(C)(C)C)C(=O)C(CC)(CC)N1OC(C)C1=CC=CC=C1 GMDHSLALCRJDCT-UHFFFAOYSA-N 0.000 description 4
- AAQFPIOHPXUGNM-UHFFFAOYSA-N 1-tert-butyl-3,3,5,5-tetraethyl-4-phenylmethoxypiperazin-2-one Chemical compound CCC1(CC)CN(C(C)(C)C)C(=O)C(CC)(CC)N1OCC1=CC=CC=C1 AAQFPIOHPXUGNM-UHFFFAOYSA-N 0.000 description 4
- MLXQULZNIANQDT-UHFFFAOYSA-N 1-tert-butyl-3,3-diethyl-5,5-dimethyl-4-phenylmethoxypiperazin-2-one Chemical compound CC1(C)CN(C(C)(C)C)C(=O)C(CC)(CC)N1OCC1=CC=CC=C1 MLXQULZNIANQDT-UHFFFAOYSA-N 0.000 description 4
- XCDAPYJGQJAAPG-UHFFFAOYSA-N 1-tert-butyl-3,3-diethyl-5,5-dimethylpiperazin-2-one Chemical compound CCC1(CC)NC(C)(C)CN(C(C)(C)C)C1=O XCDAPYJGQJAAPG-UHFFFAOYSA-N 0.000 description 4
- IONRRIGXSWYKKC-UHFFFAOYSA-N 1-tert-butyl-3,5,5-triethyl-3-methyl-4-(1-phenylethoxy)piperazin-2-one Chemical compound CCC1(CC)CN(C(C)(C)C)C(=O)C(C)(CC)N1OC(C)C1=CC=CC=C1 IONRRIGXSWYKKC-UHFFFAOYSA-N 0.000 description 4
- GUAWSHSZRSOUMW-UHFFFAOYSA-N 1-tert-butyl-3,5,5-triethyl-3-methyl-4-phenylmethoxypiperazin-2-one Chemical compound CCC1(CC)CN(C(C)(C)C)C(=O)C(C)(CC)N1OCC1=CC=CC=C1 GUAWSHSZRSOUMW-UHFFFAOYSA-N 0.000 description 4
- DEMLMDLMVWXHRC-UHFFFAOYSA-N 1-tert-butyl-3,5,5-trimethyl-3-(2-methylpropyl)-4-(1-phenylethoxy)piperazin-2-one Chemical compound CC1(C)CN(C(C)(C)C)C(=O)C(CC(C)C)(C)N1OC(C)C1=CC=CC=C1 DEMLMDLMVWXHRC-UHFFFAOYSA-N 0.000 description 4
- JZIQRHNKFBJEER-UHFFFAOYSA-N 1-tert-butyl-3,5-diethyl-3,5-dimethyl-4-(1-phenylethoxy)piperazin-2-one Chemical compound CCC1(C)CN(C(C)(C)C)C(=O)C(C)(CC)N1OC(C)C1=CC=CC=C1 JZIQRHNKFBJEER-UHFFFAOYSA-N 0.000 description 4
- JBNBGZUYAWNMDG-UHFFFAOYSA-N 1-tert-butyl-3-ethyl-3,5,5-trimethyl-4-(1-phenylethoxy)piperazin-2-one Chemical compound CC1(C)CN(C(C)(C)C)C(=O)C(CC)(C)N1OC(C)C1=CC=CC=C1 JBNBGZUYAWNMDG-UHFFFAOYSA-N 0.000 description 4
- YXHKLPCSCPINSU-UHFFFAOYSA-N 2,2,5,5-tetraethyl-1-(1-phenylethoxy)imidazolidin-4-one Chemical compound CCC1(CC)NC(=O)C(CC)(CC)N1OC(C)C1=CC=CC=C1 YXHKLPCSCPINSU-UHFFFAOYSA-N 0.000 description 4
- ARTINEXELSVQFU-UHFFFAOYSA-N 2,2,5,5-tetraethylimidazolidin-4-one Chemical compound CCC1(CC)NC(=O)C(CC)(CC)N1 ARTINEXELSVQFU-UHFFFAOYSA-N 0.000 description 4
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 4
- ITGOMIKKVVXDLE-UHFFFAOYSA-N 2,7-diethyl-2,3,4,7-tetramethyl-1-(1-phenylethoxy)-1,4-diazepan-5-one Chemical compound CCC1(C)CC(=O)N(C)C(C)C(C)(CC)N1OC(C)C1=CC=CC=C1 ITGOMIKKVVXDLE-UHFFFAOYSA-N 0.000 description 4
- UYRYNBMOGVIGBQ-UHFFFAOYSA-N 2,7-diethyl-2,3,7-trimethyl-1-(1-phenylethoxy)-1,4-diazepan-5-one Chemical compound CCC1(C)CC(=O)NC(C)C(C)(CC)N1OC(C)C1=CC=CC=C1 UYRYNBMOGVIGBQ-UHFFFAOYSA-N 0.000 description 4
- UZBHMLIATWYOHI-UHFFFAOYSA-N 2-(2,2-dibutyl-4-tert-butyl-6,6-dimethyl-3-oxopiperazin-1-yl)oxy-2-methylpropanenitrile Chemical compound CCCCC1(CCCC)N(OC(C)(C)C#N)C(C)(C)CN(C(C)(C)C)C1=O UZBHMLIATWYOHI-UHFFFAOYSA-N 0.000 description 4
- YMYLSGJIPSOSTE-UHFFFAOYSA-N 2-(2,2-diethyl-6,6-dimethyl-3-oxo-4-propan-2-ylpiperazin-1-yl)oxy-2-methylpropanenitrile Chemical compound CCC1(CC)N(OC(C)(C)C#N)C(C)(C)CN(C(C)C)C1=O YMYLSGJIPSOSTE-UHFFFAOYSA-N 0.000 description 4
- JNOKYCCKHUYBQZ-UHFFFAOYSA-N 2-(3,3-diethyl-5,5-dimethyl-2-oxomorpholin-4-yl)oxy-2-methylpropanenitrile Chemical compound CCC1(CC)N(OC(C)(C)C#N)C(C)(C)COC1=O JNOKYCCKHUYBQZ-UHFFFAOYSA-N 0.000 description 4
- AOYQRPLJAGLQQK-UHFFFAOYSA-N 2-(4-tert-butyl-2,2,6,6-tetraethyl-3-oxopiperazin-1-yl)oxy-2-methylpropanenitrile Chemical compound CCC1(CC)CN(C(C)(C)C)C(=O)C(CC)(CC)N1OC(C)(C)C#N AOYQRPLJAGLQQK-UHFFFAOYSA-N 0.000 description 4
- ZLSULMZGWDODMA-UHFFFAOYSA-N 2-(4-tert-butyl-2,2-diethyl-6,6-dimethyl-3-oxopiperazin-1-yl)oxy-2-methylpropanenitrile Chemical compound CCC1(CC)N(OC(C)(C)C#N)C(C)(C)CN(C(C)(C)C)C1=O ZLSULMZGWDODMA-UHFFFAOYSA-N 0.000 description 4
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- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 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
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- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 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
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/36—One oxygen atom with hydrocarbon radicals, substituted by nitrogen atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
- C07D265/32—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings with oxygen atoms directly attached to ring carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polymerization Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Hydrogenated Pyridines (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
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| EP98811030.0 | 1998-10-16 |
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| WO2001023435A1 (en) * | 1999-09-30 | 2001-04-05 | Noveon Ip Holdings Corp. | Polymerization compositions and methods |
| US7030196B2 (en) | 2000-05-19 | 2006-04-18 | Ciba Specialty Chemicals Corporation | Process for reducing the molecular weight of polypropylene |
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| DE10036801A1 (de) | 2000-07-28 | 2002-02-07 | Tesa Ag | Acrylathaftklebemassen mit enger Molekulargewichtsverteilung |
| TWI225492B (en) * | 2000-09-25 | 2004-12-21 | Ciba Sc Holding Ag | Composition and process for enhancing controlled free radical polymerization |
| TW574236B (en) * | 2000-09-25 | 2004-02-01 | Ciba Sc Holding Ag | Process for controlled radical polymerization in aqueous dispersion |
| JP4505980B2 (ja) * | 2000-11-28 | 2010-07-21 | 東レ株式会社 | アクリロニトリル系重合体の製造法 |
| US6544304B2 (en) | 2001-04-02 | 2003-04-08 | Ciba Specialty Chemicals Corporation | Candle wax stabilized with morpholinones |
| DE60238606D1 (de) * | 2001-06-13 | 2011-01-27 | Basf Se | 4-imin-n-alkoxy- oder oxy-polyalkyl-piperidin-verboren |
| DE10129608A1 (de) | 2001-06-20 | 2003-05-28 | Tesa Ag | Stripfähige Systeme auf Basis von Acrylatblockcopolymeren |
| DE10133727A1 (de) * | 2001-07-11 | 2003-01-23 | Borchers Gmbh | Verwendung von Mischungen spezieller organischer Verbindungen als Hautverhinderungsmittel in lufttrocknenden Lacken |
| US20030073835A1 (en) | 2001-07-31 | 2003-04-17 | Dario Lazzari | Imidazolidinone derivatives |
| DE10149084A1 (de) | 2001-10-05 | 2003-06-18 | Tesa Ag | UV-vernetzbare Acrylathaftschmelzhaftkleber mit enger Molekulargewichtsverteilung |
| DE10149083A1 (de) | 2001-10-05 | 2003-04-17 | Tesa Ag | Acrylathaftklebemassen mit enger Molekulargewichtsverteilung |
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| DE10156088A1 (de) | 2001-11-16 | 2003-06-05 | Tesa Ag | Orientierte Acrylatblockcopolymere |
| DE10157154A1 (de) * | 2001-11-22 | 2003-05-28 | Tesa Ag | Verfahren zur Herstellung orientierter Acrylathotmelts |
| JP2005510597A (ja) | 2001-11-24 | 2005-04-21 | テサ・アクチエンゲゼルシヤフト | 末端官能化ポリアクリレートの２成分架橋 |
| DE10221093A1 (de) | 2002-05-11 | 2003-11-20 | Tesa Ag | Verwendung von Makromonomeren für die Herstellung von Acrylathaftklebemassen |
| DE10234246A1 (de) | 2002-07-27 | 2004-02-05 | Tesa Ag | Haftklebemassen mit hohem Brechungsindex auf Basis von Acrylatblockcopolymeren |
| DE10237950A1 (de) * | 2002-08-20 | 2004-03-11 | Tesa Ag | UV-initiiert thermisch vernetzte Acrylathaftklebemassen |
| CA2497260A1 (en) * | 2002-09-04 | 2004-03-18 | Wiebke Wunderlich-Wippert | Method of producing comb or star copolymers using epoxy-functionalized nitroxylethers |
| DE10256782A1 (de) * | 2002-12-05 | 2004-08-05 | Tesa Ag | Haftklebeartikel |
| DE10259451A1 (de) * | 2002-12-19 | 2004-07-08 | Tesa Ag | Haftklebeartikel mit wenigstens einer Schicht aus einer thermisch leitfähigen Haftklebemasse und Verfahren zu seiner Herstellung |
| DE10314898A1 (de) | 2003-01-29 | 2004-08-12 | Tesa Ag | Haftklebebänder zur Verklebung von Druckplatten und Verfahren zu deren Herstellung |
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| DE10322830A1 (de) * | 2003-05-19 | 2004-12-09 | Tesa Ag | Verfahren zur kontinuierlichen Herstellung von Polymeren aus vinylischen Verbindungen durch Substanz-beziehungsweise Lösungsmittelpolymerisation |
| ES2303592T3 (es) * | 2003-05-30 | 2008-08-16 | Tesa Ag | Masa autoadhesiva y articulos autoadhesivos con poliacrilato y su correspondiente metodo de tratamiento de fusion en caliente. |
| DE10357323A1 (de) | 2003-12-05 | 2005-06-30 | Tesa Ag | Haftklebemasse |
| DE10357322A1 (de) | 2003-12-05 | 2005-06-30 | Tesa Ag | Zweischichtige Haftklebemasse |
| DE10359349A1 (de) * | 2003-12-16 | 2005-07-14 | Tesa Ag | Verfahren zur Herstellung von Acrylatschmelzhaftklebern |
| DE10359350A1 (de) | 2003-12-16 | 2005-07-14 | Tesa Ag | Haftklebemasse |
| DE10359973A1 (de) | 2003-12-18 | 2005-07-21 | Tesa Ag | Haftklebemasse auf Basis von Acrylatblockcopolymeren |
| DE102004001412A1 (de) | 2004-01-09 | 2005-08-25 | Tesa Ag | Haftklebemasse auf Basis eines Acrylatpolymerblends |
| JP2005232103A (ja) * | 2004-02-20 | 2005-09-02 | Nagase & Co Ltd | 光学活性なビシナルジアミンおよびその製造方法 |
| DE102004013699A1 (de) * | 2004-03-18 | 2005-10-06 | Tesa Ag | Haftklebeband für medizinische Diagnosestreifen |
| JP5138363B2 (ja) * | 2004-03-24 | 2013-02-06 | チバ ホールディング インコーポレーテッド | 制御された高圧重合によるエチレンポリマーの調製方法 |
| US20100210800A1 (en) * | 2004-03-24 | 2010-08-19 | Ciba Corporation | Method of preparing ethylene polymers by controlled high pressure polymerization |
| US8057740B2 (en) | 2004-06-23 | 2011-11-15 | Tesa Se | Medical biosensor by means of which biological liquids are analyzed |
| DE102004033242A1 (de) * | 2004-07-08 | 2006-02-02 | Tesa Ag | Haftklebemasse |
| WO2006027386A1 (de) | 2004-09-09 | 2006-03-16 | Tesa Ag | Verfahren zur herstellung von acrylhaltigen haftklebemassen |
| DE102004044085A1 (de) | 2004-09-09 | 2006-03-16 | Tesa Ag | Haftklebemasse mit dualem Vernetzungsmechanismus |
| EP1861429B1 (en) | 2005-01-11 | 2013-03-13 | Basf Se | Process for the post-modification of homo and copolymers prepared by controlled free radical polymerization processes |
| US7410694B2 (en) | 2005-04-11 | 2008-08-12 | Tesa Aktiengesellschaft | Adhesive |
| DE102006035786A1 (de) * | 2006-07-28 | 2008-03-13 | Tesa Ag | Haftklebefolie mit hoher optischer Transparenz zur Verklebung als Splitterschutz auf Glasscheiben in Konsumgüterelektronikbauteilen |
| DE102006042816A1 (de) * | 2006-09-08 | 2008-06-26 | Tesa Ag | Hitze-aktiviert verklebbares Stanzungsflächenelement |
| WO2008032732A1 (en) * | 2006-09-15 | 2008-03-20 | Kuraray Co., Ltd. | Methacrylic resin composition, resin modifier, and molded body |
| WO2008110466A1 (en) * | 2007-03-09 | 2008-09-18 | Basf Se | Nitroxides for lithium-ion batteries |
| US20080247975A1 (en) * | 2007-04-05 | 2008-10-09 | Dueva-Koganov Olga V | Sunscreen and personal care compositions comprising a select copolymer |
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| WO2008145595A1 (en) * | 2007-06-01 | 2008-12-04 | Basf Se | Modified printable surfaces |
| DE102007038458A1 (de) | 2007-08-14 | 2009-02-19 | Tesa Ag | Verbundelement |
| DE102007045166A1 (de) * | 2007-09-20 | 2009-04-02 | Tesa Ag | Transparentes Klebeband |
| DE102007045168A1 (de) | 2007-09-20 | 2009-04-02 | Tesa Ag | Transparentes Klebeband |
| DE102007062447A1 (de) | 2007-12-20 | 2009-06-25 | Tesa Ag | Doppelseitiges Haftklebeband für Flüssigkristallanzeigesysteme |
| CN102131488A (zh) * | 2008-06-04 | 2011-07-20 | 宝洁公司 | 义齿粘合剂组合物和方法 |
| EP2385937A1 (en) * | 2009-01-08 | 2011-11-16 | Basf Se | Polymerisation initiator |
| DE102009006593A1 (de) | 2009-01-29 | 2010-08-05 | Tesa Se | Verfahren zur Korrosionsschutzbehandlung von Metalloberflächen |
| DE102009007589A1 (de) | 2009-02-05 | 2010-08-12 | Tesa Se | Transfer-Haftklebeband sowie Verfahren zur Herstellung eines Haftklebebandes |
| CN102803208B (zh) | 2009-06-12 | 2014-04-30 | 3M创新有限公司 | 氟化芳香族含双(酰基)化合物和由其制备的聚酯 |
| US9309391B2 (en) | 2010-06-29 | 2016-04-12 | Basf Se | Process for improving the flow of properties of polymer melts |
| DE102011077927A1 (de) | 2011-06-21 | 2012-12-27 | Tesa Se | Verfahren zur reversiblen kovalenten Vernetzung von Klebemassen |
| RU2014120925A (ru) | 2011-10-25 | 2015-12-10 | Басф Се | Применение гребенчатых или блок-сополимеров в качестве средств против повторного осаждения загрязнения и грязеотталкивающих средств в процессах стирки |
| DE102012208597B4 (de) | 2012-05-23 | 2018-05-30 | Tesa Se | Haftklebemasse für medizinische Zwecke, Verfahren zu ihrer Herstellung und die Haftklebmasse enthaltende Mischung |
| DE102012212883A1 (de) | 2012-07-23 | 2014-05-15 | Tesa Se | Geschäumtes Klebeband zur Verklebung auf unpolaren Oberflächen |
| US9790452B2 (en) | 2013-03-27 | 2017-10-17 | Basf Se | Block copolymers as soil release agents in laundry processes |
| DE102013224774A1 (de) | 2013-12-03 | 2015-06-03 | Tesa Se | Mehrschichtiges Produkt |
| DE102015222028A1 (de) | 2015-11-09 | 2017-05-11 | Tesa Se | Kationisch polymerisierbare Polyacrylate enthaltend Alkoxysilangruppen und deren Verwendung |
| DE102016207548A1 (de) | 2016-05-02 | 2017-11-02 | Tesa Se | Härtbare Klebemasse und darauf basierende Reaktivklebebänder |
| DE102016207540A1 (de) | 2016-05-02 | 2017-11-02 | Tesa Se | Wasserdampfsperrende Klebemasse mit hochfunktionalisiertem Poly(meth)acrylat |
| DE102016207550A1 (de) | 2016-05-02 | 2017-11-02 | Tesa Se | Funktionalisierte (Co)Polymere für Klebesysteme und Klebebänder |
| CN110023265B (zh) * | 2016-11-22 | 2022-07-15 | Sika技术股份公司 | 通过硝基氧调介的溶液聚合生产分散剂 |
| DE102017223147A1 (de) | 2017-12-19 | 2019-06-19 | Tesa Se | Oberflächenschutzfolie mit Schaumschicht |
| DE102018216868A1 (de) | 2018-10-01 | 2020-04-02 | Tesa Se | Latent reaktiver Klebefilm |
| DE102019215890A1 (de) | 2019-10-16 | 2021-04-22 | Tesa Se | Härtbare Klebemasse und darauf basierende Reaktivklebebänder |
| DE102019219166B4 (de) | 2019-12-09 | 2023-08-24 | Tesa Se | Strukturelle Haftklebemasse und ihre Verwendung |
| DE102020203952A1 (de) | 2020-03-26 | 2021-09-30 | Tesa Se | Latent reaktiver Klebefilm |
| CN116490535A (zh) | 2020-11-30 | 2023-07-25 | 巴斯夫欧洲公司 | 制备聚合物分散体的方法 |
| US20240182746A1 (en) | 2021-03-26 | 2024-06-06 | Basf Se | Polymer composition comprising polyacrylic block copolymer and aromatic based polyalkyleneoxide as dispersant |
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| GB1194402A (en) * | 1966-06-15 | 1970-06-10 | Sankyo Co | 2,2,5,5-Tetrasubstituted-4-Oxoimidazolidine Nitroxide and Process for Preparing the Same |
| DE1299627B (de) * | 1966-08-31 | 1969-07-24 | Dynamit Nobel Ag | Verfahren zur Herstellung von reinster Terepthalsaeure |
| JPS462905B1 (enExample) * | 1967-11-28 | 1971-01-25 | ||
| JPS5010281B1 (enExample) * | 1970-03-20 | 1975-04-19 | ||
| AU571240B2 (en) * | 1983-07-11 | 1988-04-14 | Commonwealth Scientific And Industrial Research Organisation | Alkoxy-amines, useful as initiators |
| US4581429A (en) * | 1983-07-11 | 1986-04-08 | Commonwealth Scientific And Industrial Research Organization | Polymerization process and polymers produced thereby |
| FR2730240A1 (fr) | 1995-02-07 | 1996-08-09 | Atochem Elf Sa | Stabilisation d'un polymere par un radical libre stable |
| US5608023A (en) | 1995-03-30 | 1997-03-04 | Xerox Corporation | Rate enhanced polymerization processes |
| AU4773997A (en) * | 1996-09-25 | 1998-04-17 | Akzo Nobel N.V. | No-compounds for pseudo-living radical polymerization |
| US6271340B1 (en) * | 1997-01-10 | 2001-08-07 | E. I. Du Pont De Nemours And Company | Method of controlling polymer molecular weight and structure |
| US6281311B1 (en) * | 1997-03-31 | 2001-08-28 | Pmd Holdings Corp. | Controlled free radical polymerization process |
| TW557313B (en) * | 1998-02-02 | 2003-10-11 | Ciba Sc Holding Ag | Oxopiperazinyl derivatives and light stabilized compositions |
| TW495515B (en) * | 1998-03-09 | 2002-07-21 | Ciba Sc Holding Ag | 1-alkoxy-polyalkyl-piperidine derivatives, a polymerizable composition containing the same and a process for polymerization |
| CH693416A5 (de) | 1998-03-09 | 2003-07-31 | Ciba Sc Holding Ag | 1-Alkoxypolyalkylpiperidinderivate und ihre Verwendung als Polymerisationsregler. |
| TW482806B (en) * | 1998-06-02 | 2002-04-11 | Ciba Sc Holding Ag | Compositions stabilized by dioxopiperazinyl derivatives |
| TW541303B (en) | 2000-03-22 | 2003-07-11 | Ciba Sc Holding Ag | 2,2,6,6 diethyl-dimethyl-1-alkoxy-piperidine compounds and their corresponding 1-oxides |
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- 1999-10-12 IT IT1999MI002125A patent/IT1313663B1/it active
- 1999-10-13 DK DK199901463A patent/DK199901463A/da not_active Application Discontinuation
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- 1999-10-14 FR FR9912810A patent/FR2784684B1/fr not_active Expired - Lifetime
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| ES2178908B1 (es) | 2004-04-01 |
| AU769061B2 (en) | 2004-01-15 |
| BE1012727A5 (fr) | 2001-02-06 |
| GB9923579D0 (en) | 1999-12-08 |
| CN100343285C (zh) | 2007-10-17 |
| CN1253954A (zh) | 2000-05-24 |
| ES2178908A1 (es) | 2003-01-01 |
| BR9904685A (pt) | 2000-11-28 |
| FR2784684A1 (fr) | 2000-04-21 |
| GB2342649B (en) | 2001-07-18 |
| US20030125494A1 (en) | 2003-07-03 |
| AU5361799A (en) | 2000-04-20 |
| DE19949352A1 (de) | 2000-04-20 |
| CA2286375A1 (en) | 2000-04-16 |
| US6664353B2 (en) | 2003-12-16 |
| NL1013259A1 (nl) | 2000-04-18 |
| ITMI992125A0 (it) | 1999-10-12 |
| GB2342649A (en) | 2000-04-19 |
| US6479608B1 (en) | 2002-11-12 |
| NL1013259C2 (nl) | 2000-11-21 |
| KR20000029079A (ko) | 2000-05-25 |
| SE9903593D0 (sv) | 1999-10-06 |
| ITMI992125A1 (it) | 2001-04-12 |
| JP2000128869A (ja) | 2000-05-09 |
| SE522619C2 (sv) | 2004-02-24 |
| DE19949352B4 (de) | 2015-05-28 |
| IT1313663B1 (it) | 2002-09-09 |
| DK199901463A (da) | 2000-04-17 |
| TWI225483B (en) | 2004-12-21 |
| KR100597892B1 (ko) | 2006-07-06 |
| SE9903593L (sv) | 2000-04-17 |
| FR2784684B1 (fr) | 2001-01-26 |
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