CN100343285C - 在受控的自由基聚合方法中作为调节剂的杂环烷氧基胺 - Google Patents
在受控的自由基聚合方法中作为调节剂的杂环烷氧基胺 Download PDFInfo
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- CN100343285C CN100343285C CNB991213904A CN99121390A CN100343285C CN 100343285 C CN100343285 C CN 100343285C CN B991213904 A CNB991213904 A CN B991213904A CN 99121390 A CN99121390 A CN 99121390A CN 100343285 C CN100343285 C CN 100343285C
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- -1 Heterocyclic alkoxyl amine Chemical class 0.000 title claims abstract description 130
- 238000000034 method Methods 0.000 title claims abstract description 33
- 238000010526 radical polymerization reaction Methods 0.000 title claims description 13
- 239000000178 monomer Substances 0.000 claims abstract description 189
- 150000003254 radicals Chemical class 0.000 claims abstract description 144
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 126
- 239000000203 mixture Substances 0.000 claims abstract description 125
- 239000003999 initiator Substances 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 400
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 123
- 229910052739 hydrogen Inorganic materials 0.000 claims description 82
- 239000001257 hydrogen Substances 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- 150000002431 hydrogen Chemical group 0.000 claims description 49
- 229910052799 carbon Inorganic materials 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 229920000642 polymer Polymers 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 17
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 16
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-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 14
- 229920001400 block copolymer Polymers 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 238000003776 cleavage reaction Methods 0.000 claims description 7
- 230000007017 scission Effects 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 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 claims description 6
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 6
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 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 claims description 5
- 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 claims description 5
- 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 claims description 5
- 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 claims description 5
- LYDWSNZBYCAGPK-UHFFFAOYSA-N 2-(4-tert-butyl-2,6,6-triethyl-2-methyl-3-oxopiperazin-1-yl)oxy-2-methylpropanenitrile Chemical compound CCC1(C)N(OC(C)(C)C#N)C(CC)(CC)CN(C(C)(C)C)C1=O LYDWSNZBYCAGPK-UHFFFAOYSA-N 0.000 claims description 5
- HWDPFCCKBAFQRC-UHFFFAOYSA-N 2-(4-tert-butyl-6,6-diethyl-2,2-dimethyl-3-oxopiperazin-1-yl)oxy-2-methylpropanenitrile Chemical compound CCC1(CC)CN(C(C)(C)C)C(=O)C(C)(C)N1OC(C)(C)C#N HWDPFCCKBAFQRC-UHFFFAOYSA-N 0.000 claims description 5
- SHEIKGMYXDSXQG-UHFFFAOYSA-N 2-(4-tert-butyl-6,6-dimethyl-3-oxo-2,2-dipropylpiperazin-1-yl)oxy-2-methylpropanenitrile Chemical compound CCCC1(CCC)N(OC(C)(C)C#N)C(C)(C)CN(C(C)(C)C)C1=O SHEIKGMYXDSXQG-UHFFFAOYSA-N 0.000 claims description 5
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 5
- RQSJAQMWOGLLAU-UHFFFAOYSA-N 4-benzyl-2,7-diethyl-2,3,7-trimethyl-1-phenylmethoxy-1,4-diazepan-5-one Chemical compound CC1C(C)(CC)N(OCC=2C=CC=CC=2)C(CC)(C)CC(=O)N1CC1=CC=CC=C1 RQSJAQMWOGLLAU-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 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 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
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 229920005604 random copolymer Polymers 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 230000000977 initiatory effect Effects 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 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
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 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
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 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
- 150000001993 dienes Chemical class 0.000 claims description 2
- 230000000694 effects Effects 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
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound 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
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 2
- 125000005250 alkyl acrylate group Chemical group 0.000 claims 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 239000002243 precursor Substances 0.000 abstract description 8
- 150000001412 amines Chemical class 0.000 abstract description 7
- 125000005262 alkoxyamine group Chemical group 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 142
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 138
- 239000000243 solution Substances 0.000 description 102
- 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 73
- 229910052786 argon Inorganic materials 0.000 description 71
- 239000007788 liquid Substances 0.000 description 70
- 238000004364 calculation method Methods 0.000 description 59
- 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
- 238000002844 melting Methods 0.000 description 50
- 230000008018 melting Effects 0.000 description 50
- 238000005160 1H NMR spectroscopy Methods 0.000 description 46
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 34
- 239000012230 colorless oil Substances 0.000 description 34
- 238000000921 elemental analysis Methods 0.000 description 32
- 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
- 238000004458 analytical method Methods 0.000 description 28
- 238000001704 evaporation Methods 0.000 description 28
- 230000008020 evaporation Effects 0.000 description 27
- 239000013078 crystal Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- 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
- 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 20
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 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 17
- 239000002904 solvent Substances 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 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
- 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 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 9
- 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
- 238000003756 stirring Methods 0.000 description 9
- 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 8
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 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 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 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 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
- 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
- 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
- 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
- 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 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
- 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
- 229920000578 graft copolymer Polymers 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 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 4
- 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 4
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- VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical class O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BUGISVZCMXHOHO-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-2-[[1-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCC(CO)(CO)NC(=O)C(C)(C)N=NC(C)(C)C(=O)NC(CO)(CO)CO BUGISVZCMXHOHO-UHFFFAOYSA-N 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- CATWEXRJGNBIJD-UHFFFAOYSA-N n-tert-butyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NC(C)(C)C CATWEXRJGNBIJD-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 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
- 125000001117 oleyl 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])=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])[H] 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- QRMPKOFEUHIBNM-UHFFFAOYSA-N p-dimethylcyclohexane Natural products CC1CCC(C)CC1 QRMPKOFEUHIBNM-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical group CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005553 polystyrene-acrylate Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 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
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- KQYLUTYUZIVHND-UHFFFAOYSA-N tert-butyl 2,2-dimethyloctaneperoxoate Chemical compound CCCCCCC(C)(C)C(=O)OOC(C)(C)C KQYLUTYUZIVHND-UHFFFAOYSA-N 0.000 description 1
- 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
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-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
- ZUSDEBDNDIJDMZ-UHFFFAOYSA-N tert-butyl 7-methyloctaneperoxoate Chemical compound CC(C)CCCCCC(=O)OOC(C)(C)C ZUSDEBDNDIJDMZ-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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229920000428 triblock copolymer Polymers 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 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
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
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)
- Hydrogenated Pyridines (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (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)
| Publication Number | Publication Date |
|---|---|
| CN1253954A CN1253954A (zh) | 2000-05-24 |
| CN100343285C true CN100343285C (zh) | 2007-10-17 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB991213904A Expired - Fee Related CN100343285C (zh) | 1998-10-16 | 1999-10-15 | 在受控的自由基聚合方法中作为调节剂的杂环烷氧基胺 |
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|---|---|
| US (2) | US6479608B1 (enExample) |
| JP (1) | JP4895416B2 (enExample) |
| KR (1) | KR100597892B1 (enExample) |
| CN (1) | CN100343285C (enExample) |
| AU (1) | AU769061B2 (enExample) |
| BE (1) | BE1012727A5 (enExample) |
| BR (1) | BR9904685A (enExample) |
| CA (1) | CA2286375A1 (enExample) |
| DE (1) | DE19949352B4 (enExample) |
| DK (1) | DK199901463A (enExample) |
| ES (1) | ES2178908B1 (enExample) |
| FR (1) | FR2784684B1 (enExample) |
| GB (1) | GB2342649B (enExample) |
| IT (1) | IT1313663B1 (enExample) |
| NL (1) | NL1013259C2 (enExample) |
| SE (1) | SE522619C2 (enExample) |
| TW (1) | TWI225483B (enExample) |
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| US6875831B1 (en) | 1999-07-02 | 2005-04-05 | Ciba Specialty Chemicals Corp. | Mono and multifunctional alkoxyamines for the preparation of functionalized macromers |
| 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 |
| KR100842407B1 (ko) * | 2000-05-19 | 2008-07-01 | 시바 홀딩 인코포레이티드 | 폴리에틸렌 또는 폴리에틸렌 배합물의 분자량 제어 증가방법 |
| DE10036801A1 (de) | 2000-07-28 | 2002-02-07 | Tesa Ag | Acrylathaftklebemassen mit enger Molekulargewichtsverteilung |
| TW574236B (en) * | 2000-09-25 | 2004-02-01 | Ciba Sc Holding Ag | Process for controlled radical polymerization in aqueous dispersion |
| 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 |
| 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 |
| DE10149083A1 (de) | 2001-10-05 | 2003-04-17 | Tesa Ag | Acrylathaftklebemassen mit enger Molekulargewichtsverteilung |
| DE10149084A1 (de) | 2001-10-05 | 2003-06-18 | Tesa Ag | UV-vernetzbare Acrylathaftschmelzhaftkleber 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 |
| WO2003046030A1 (de) | 2001-11-24 | 2003-06-05 | Tesa Ag | Vernetzung von photoinitiator-initialisierten polyacrylaten |
| 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 |
| EP1534765B1 (en) * | 2002-09-04 | 2008-12-17 | Ciba Holding Inc. | 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 |
| DE10312062A1 (de) * | 2003-03-18 | 2004-09-30 | Tesa Ag | Schmelzhaftkleber mit geringem Rückschrumpf, Verfahren zu seiner Herstellung und Verwendung |
| DE10322830A1 (de) * | 2003-05-19 | 2004-12-09 | Tesa Ag | Verfahren zur kontinuierlichen Herstellung von Polymeren aus vinylischen Verbindungen durch Substanz-beziehungsweise Lösungsmittelpolymerisation |
| EP1633829B1 (de) * | 2003-05-30 | 2008-04-09 | Tesa AG | Polyacrylathaltige haftklebemasse und -artikel sowie zugehöriges hotmelt-verarbeitungsverfahren |
| DE10357322A1 (de) | 2003-12-05 | 2005-06-30 | Tesa Ag | Zweischichtige Haftklebemasse |
| DE10357323A1 (de) | 2003-12-05 | 2005-06-30 | Tesa Ag | 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 |
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- 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 AU AU53617/99A patent/AU769061B2/en not_active Ceased
- 1999-10-12 IT IT1999MI002125A patent/IT1313663B1/it active
- 1999-10-12 BE BE9900673A patent/BE1012727A5/fr not_active IP Right Cessation
- 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 BR BR9904685-7A patent/BR9904685A/pt not_active Application Discontinuation
- 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
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| WO1998030601A2 (en) * | 1997-01-10 | 1998-07-16 | E.I. Du Pont De Nemours And Company | Method of controlling polymer molecular weight and structure |
| WO1998044008A1 (en) * | 1997-03-31 | 1998-10-08 | The B.F. Goodrich Company | Controlled free radical polymerization process |
Also Published As
| Publication number | Publication date |
|---|---|
| NL1013259C2 (nl) | 2000-11-21 |
| IT1313663B1 (it) | 2002-09-09 |
| AU769061B2 (en) | 2004-01-15 |
| CN1253954A (zh) | 2000-05-24 |
| BE1012727A5 (fr) | 2001-02-06 |
| SE9903593L (sv) | 2000-04-17 |
| NL1013259A1 (nl) | 2000-04-18 |
| US6479608B1 (en) | 2002-11-12 |
| ES2178908B1 (es) | 2004-04-01 |
| JP2000128869A (ja) | 2000-05-09 |
| GB9923579D0 (en) | 1999-12-08 |
| JP4895416B2 (ja) | 2012-03-14 |
| CA2286375A1 (en) | 2000-04-16 |
| ITMI992125A1 (it) | 2001-04-12 |
| BR9904685A (pt) | 2000-11-28 |
| KR100597892B1 (ko) | 2006-07-06 |
| ES2178908A1 (es) | 2003-01-01 |
| US6664353B2 (en) | 2003-12-16 |
| FR2784684A1 (fr) | 2000-04-21 |
| ITMI992125A0 (it) | 1999-10-12 |
| GB2342649A (en) | 2000-04-19 |
| DK199901463A (da) | 2000-04-17 |
| US20030125494A1 (en) | 2003-07-03 |
| TWI225483B (en) | 2004-12-21 |
| KR20000029079A (ko) | 2000-05-25 |
| DE19949352A1 (de) | 2000-04-20 |
| SE522619C2 (sv) | 2004-02-24 |
| FR2784684B1 (fr) | 2001-01-26 |
| SE9903593D0 (sv) | 1999-10-06 |
| GB2342649B (en) | 2001-07-18 |
| AU5361799A (en) | 2000-04-20 |
| DE19949352B4 (de) | 2015-05-28 |
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