DE19949352B4 - Heterocyclische Alkoxyamine als Regulatoren in gesteuerten radikalischen Polymerisationsverfahren - Google Patents
Heterocyclische Alkoxyamine als Regulatoren in gesteuerten radikalischen Polymerisationsverfahren Download PDFInfo
- Publication number
- DE19949352B4 DE19949352B4 DE19949352.9A DE19949352A DE19949352B4 DE 19949352 B4 DE19949352 B4 DE 19949352B4 DE 19949352 A DE19949352 A DE 19949352A DE 19949352 B4 DE19949352 B4 DE 19949352B4
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- compound
- methyl
- hydrogen
- phenyl
- 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
- 238000010526 radical polymerization reaction Methods 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 412
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 228
- 239000000178 monomer Substances 0.000 claims abstract description 199
- 239000000203 mixture Substances 0.000 claims abstract description 120
- 239000001257 hydrogen Substances 0.000 claims abstract description 113
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 105
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 41
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 31
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 126
- 125000000217 alkyl group Chemical group 0.000 claims description 110
- -1 ethylene, propylene Chemical group 0.000 claims description 87
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 85
- 150000003254 radicals Chemical class 0.000 claims description 60
- 150000002431 hydrogen Chemical class 0.000 claims description 37
- 229920000642 polymer Polymers 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 28
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 16
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 229920001400 block copolymer Polymers 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 8
- 238000003776 cleavage reaction Methods 0.000 claims description 7
- 230000007017 scission Effects 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 6
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 229920005604 random copolymer Polymers 0.000 claims description 3
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- SYNHCENRCUAUNM-UHFFFAOYSA-N Nitrogen mustard N-oxide hydrochloride Chemical group Cl.ClCC[N+]([O-])(C)CCCl SYNHCENRCUAUNM-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003926 acrylamides Chemical class 0.000 claims description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 2
- 150000008360 acrylonitriles Chemical class 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims description 2
- 230000005670 electromagnetic radiation Effects 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical class C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 claims description 2
- 238000000527 sonication Methods 0.000 claims description 2
- 150000003440 styrenes Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 146
- 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 127
- 239000000243 solution Substances 0.000 description 103
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 92
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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 75
- 229910052786 argon Inorganic materials 0.000 description 73
- 239000007788 liquid Substances 0.000 description 71
- 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
- 238000004458 analytical method Methods 0.000 description 36
- 239000012230 colorless oil Substances 0.000 description 35
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 34
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 32
- 239000003921 oil Substances 0.000 description 30
- 238000001704 evaporation Methods 0.000 description 27
- 230000008020 evaporation Effects 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000013078 crystal Substances 0.000 description 25
- 238000000921 elemental analysis Methods 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 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 22
- 125000003342 alkenyl group Chemical group 0.000 description 22
- 125000000304 alkynyl group Chemical group 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000009826 distribution Methods 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 19
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 19
- 0 CC(*)(N(C)C(C1(*)*)=O)N1O* Chemical compound CC(*)(N(C)C(C1(*)*)=O)N1O* 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 229910052736 halogen Inorganic materials 0.000 description 18
- 150000002367 halogens Chemical class 0.000 description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 12
- 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 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 11
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 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
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 125000003884 phenylalkyl group Chemical group 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- 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
- 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 6
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-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
- 239000003795 chemical substances by application Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 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
- 238000003786 synthesis reaction Methods 0.000 description 6
- 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
- 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 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
- YSLQIELHSIUJTR-UHFFFAOYSA-N 3,3-diethyl-5,5-dimethylmorpholin-2-one Chemical compound CCC1(CC)NC(C)(C)COC1=O YSLQIELHSIUJTR-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000006184 cosolvent Substances 0.000 description 5
- 229920000578 graft copolymer Polymers 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 125000004400 (C1-C12) alkyl group Chemical group 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
- 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
- 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
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- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- KHJNXCATZZIGAX-UHFFFAOYSA-N tert-butyl 2-ethyl-2-methylheptaneperoxoate Chemical compound CCCCCC(C)(CC)C(=O)OOC(C)(C)C KHJNXCATZZIGAX-UHFFFAOYSA-N 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- 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
- 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
Landscapes
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98811030.0 | 1998-10-16 | ||
| EP98811030 | 1998-10-16 |
Publications (2)
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| DE19949352A1 DE19949352A1 (de) | 2000-04-20 |
| DE19949352B4 true DE19949352B4 (de) | 2015-05-28 |
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| DE19949352.9A Expired - Lifetime DE19949352B4 (de) | 1998-10-16 | 1999-10-13 | Heterocyclische Alkoxyamine als Regulatoren in gesteuerten radikalischen Polymerisationsverfahren |
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| NL (1) | NL1013259C2 (https=) |
| SE (1) | SE522619C2 (https=) |
| TW (1) | TWI225483B (https=) |
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| AU7843300A (en) * | 1999-09-30 | 2001-04-30 | 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 |
| BR0110854B1 (pt) * | 2000-05-19 | 2017-10-24 | Ciba Specialty Chemicals Holdings Inc | Method for reducing the polypropylene molecular weight, propylene copolymers or polypropylene mixtures, as a compound |
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| TWI225492B (en) † | 2000-09-25 | 2004-12-21 | Ciba Sc Holding Ag | Composition and process for enhancing controlled free radical polymerization |
| 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 |
| ATE491687T1 (de) * | 2001-06-13 | 2011-01-15 | Basf Se | 4-imin-n-alkoxy- oder oxy-polyalkyl-piperidin- verbindungen zur verwendung als polymerisationsregulatoren |
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| US20030073835A1 (en) | 2001-07-31 | 2003-04-17 | Dario Lazzari | Imidazolidinone derivatives |
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| DE10149083A1 (de) | 2001-10-05 | 2003-04-17 | Tesa Ag | Acrylathaftklebemassen mit enger Molekulargewichtsverteilung |
| DE10153677A1 (de) | 2001-10-31 | 2003-05-15 | Tesa Ag | Doppelseitiges Klebeband |
| 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 |
| US7402632B2 (en) | 2001-11-24 | 2008-07-22 | Tesa Aktiengesellschaft | 2-Component crosslink of end-functionalized polyacrylates |
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| DE10237950A1 (de) * | 2002-08-20 | 2004-03-11 | Tesa Ag | UV-initiiert thermisch vernetzte Acrylathaftklebemassen |
| AU2003267011A1 (en) * | 2002-09-04 | 2004-03-29 | Ciba Specialty Chemicals Holding Inc. | Method of producing comb or star copolymers using epoxy-functionalized nitroxylethers |
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| DE10357323A1 (de) | 2003-12-05 | 2005-06-30 | Tesa Ag | Haftklebemasse |
| DE10359350A1 (de) | 2003-12-16 | 2005-07-14 | Tesa Ag | Haftklebemasse |
| DE10359349A1 (de) * | 2003-12-16 | 2005-07-14 | Tesa Ag | Verfahren zur Herstellung von Acrylatschmelzhaftklebern |
| DE10359973A1 (de) | 2003-12-18 | 2005-07-21 | Tesa Ag | Haftklebemasse auf Basis von Acrylatblockcopolymeren |
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| DE102004013699A1 (de) * | 2004-03-18 | 2005-10-06 | Tesa Ag | Haftklebeband für medizinische Diagnosestreifen |
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| US20100210800A1 (en) | 2004-03-24 | 2010-08-19 | Ciba Corporation | Method of preparing ethylene polymers by controlled high pressure polymerization |
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| DE102004033242A1 (de) * | 2004-07-08 | 2006-02-02 | Tesa Ag | Haftklebemasse |
| DE102004044085A1 (de) | 2004-09-09 | 2006-03-16 | Tesa Ag | Haftklebemasse mit dualem Vernetzungsmechanismus |
| US7851574B2 (en) | 2004-09-09 | 2010-12-14 | Tesa Se | Functionalized polymers or contact adhesive masses |
| RU2401281C2 (ru) | 2005-01-11 | 2010-10-10 | Циба Спешиалти Кемикэлз Холдинг Инк. | Способ постмодификации гомо- и сополимеров, полученных регулируемыми процессами свободнорадикальной полимеризации |
| 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 |
| US8163844B2 (en) * | 2006-09-15 | 2012-04-24 | Kuraray Co., Ltd. | Methacrylic resin composition, resin modifier, and molded article |
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| JP2010523519A (ja) * | 2007-04-05 | 2010-07-15 | ビーエーエスエフ ソシエタス・ヨーロピア | 選択されたコポリマーを含んでいる日焼け止め剤及びパーソナルケア組成物 |
| DE102007019131A1 (de) | 2007-04-20 | 2008-10-23 | Tesa Ag | Doppelseitiges Haftklebeband |
| 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 |
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| BRPI0913398A2 (pt) * | 2008-06-04 | 2015-11-24 | Procter & Gamble | composição e métodos de adesivo para dentaduras |
| JP5570529B2 (ja) * | 2009-01-08 | 2014-08-13 | ビーエーエスエフ ソシエタス・ヨーロピア | 重合開始剤 |
| 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 |
| US8686179B2 (en) | 2009-06-12 | 2014-04-01 | 3M Innovative Properties Company | Fluorinated aromatic bis(acyl)-containing compounds and polyesters prepared therefrom |
| JP5930318B2 (ja) | 2010-06-29 | 2016-06-08 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ポリマー溶融物の流動特性を向上するための方法 |
| DE102011077927A1 (de) | 2011-06-21 | 2012-12-27 | Tesa Se | Verfahren zur reversiblen kovalenten Vernetzung von Klebemassen |
| CA2853318A1 (en) | 2011-10-25 | 2013-05-02 | Basf Se | Use of comb or block copolymers as soil antiredeposition agents and soil release agents in laundry processes |
| 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 |
| 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 |
| DE102016207548A1 (de) | 2016-05-02 | 2017-11-02 | Tesa Se | Härtbare Klebemasse und darauf basierende Reaktivklebebänder |
| US11028213B2 (en) * | 2016-11-22 | 2021-06-08 | Sika Technology Ag | Production of dispersants by nitroxide-mediated solution polymerization |
| 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 |
| EP4251665B1 (en) | 2020-11-30 | 2025-01-08 | Basf Se | Process of producing polymer dispersions |
| WO2022200398A1 (en) | 2021-03-26 | 2022-09-29 | Basf Se | Polymer composition comprising polyacrylic block copolymer and aromatic based polyalkyleneoxide as dispersant |
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- 1999-08-30 TW TW088115002A patent/TWI225483B/zh active
- 1999-10-06 GB GB9923579A patent/GB2342649B/en not_active Expired - Fee Related
- 1999-10-06 SE SE9903593A patent/SE522619C2/sv not_active IP Right Cessation
- 1999-10-11 NL NL1013259A patent/NL1013259C2/nl not_active IP Right Cessation
- 1999-10-12 BE BE9900673A patent/BE1012727A5/fr not_active IP Right Cessation
- 1999-10-12 AU AU53617/99A patent/AU769061B2/en not_active Ceased
- 1999-10-12 IT IT1999MI002125A patent/IT1313663B1/it active
- 1999-10-13 DK DK199901463A patent/DK199901463A/da not_active Application Discontinuation
- 1999-10-13 DE DE19949352.9A patent/DE19949352B4/de not_active Expired - Lifetime
- 1999-10-14 FR FR9912810A patent/FR2784684B1/fr not_active Expired - Lifetime
- 1999-10-14 KR KR1019990044561A patent/KR100597892B1/ko not_active Expired - Fee Related
- 1999-10-14 CA CA002286375A patent/CA2286375A1/en not_active Abandoned
- 1999-10-14 US US09/417,538 patent/US6479608B1/en not_active Expired - Lifetime
- 1999-10-14 ES ES009902254A patent/ES2178908B1/es not_active Expired - Fee Related
- 1999-10-15 CN CNB991213904A patent/CN100343285C/zh not_active Expired - Fee Related
- 1999-10-15 JP JP29369799A patent/JP4895416B2/ja not_active Expired - Lifetime
- 1999-10-15 BR BR9904685-7A patent/BR9904685A/pt not_active Application Discontinuation
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Also Published As
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| NL1013259C2 (nl) | 2000-11-21 |
| ITMI992125A1 (it) | 2001-04-12 |
| TWI225483B (en) | 2004-12-21 |
| AU5361799A (en) | 2000-04-20 |
| JP2000128869A (ja) | 2000-05-09 |
| JP4895416B2 (ja) | 2012-03-14 |
| ES2178908A1 (es) | 2003-01-01 |
| SE9903593L (sv) | 2000-04-17 |
| US6479608B1 (en) | 2002-11-12 |
| SE9903593D0 (sv) | 1999-10-06 |
| GB9923579D0 (en) | 1999-12-08 |
| FR2784684A1 (fr) | 2000-04-21 |
| IT1313663B1 (it) | 2002-09-09 |
| US20030125494A1 (en) | 2003-07-03 |
| ES2178908B1 (es) | 2004-04-01 |
| BR9904685A (pt) | 2000-11-28 |
| GB2342649A (en) | 2000-04-19 |
| GB2342649B (en) | 2001-07-18 |
| NL1013259A1 (nl) | 2000-04-18 |
| KR20000029079A (ko) | 2000-05-25 |
| AU769061B2 (en) | 2004-01-15 |
| SE522619C2 (sv) | 2004-02-24 |
| DE19949352A1 (de) | 2000-04-20 |
| BE1012727A5 (fr) | 2001-02-06 |
| CN1253954A (zh) | 2000-05-24 |
| DK199901463A (da) | 2000-04-17 |
| FR2784684B1 (fr) | 2001-01-26 |
| CA2286375A1 (en) | 2000-04-16 |
| US6664353B2 (en) | 2003-12-16 |
| CN100343285C (zh) | 2007-10-17 |
| ITMI992125A0 (it) | 1999-10-12 |
| KR100597892B1 (ko) | 2006-07-06 |
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