TWI225483B - Heterocyclic alkoxyamines as regulators in controlled radical polymerization process - Google Patents
Heterocyclic alkoxyamines as regulators in controlled radical polymerization process Download PDFInfo
- Publication number
- TWI225483B TWI225483B TW088115002A TW88115002A TWI225483B TW I225483 B TWI225483 B TW I225483B TW 088115002 A TW088115002 A TW 088115002A TW 88115002 A TW88115002 A TW 88115002A TW I225483 B TWI225483 B TW I225483B
- Authority
- TW
- Taiwan
- Prior art keywords
- tert
- butyl
- diethyl
- compound
- alkyl
- Prior art date
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- 238000010526 radical polymerization reaction Methods 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 373
- -1 heterocyclic amines Chemical class 0.000 claims abstract description 169
- 239000000178 monomer Substances 0.000 claims abstract description 167
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 121
- 239000000203 mixture Substances 0.000 claims abstract description 76
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 63
- 239000001257 hydrogen Substances 0.000 claims abstract description 60
- 238000000034 method Methods 0.000 claims abstract description 54
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 54
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 22
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 4
- 230000000977 initiatory effect Effects 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 137
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 64
- 239000001301 oxygen Substances 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 36
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 32
- 229920000642 polymer Polymers 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 21
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 19
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 18
- 125000004429 atom Chemical group 0.000 claims description 18
- 229920001400 block copolymer Polymers 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 238000012856 packing Methods 0.000 claims description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 239000005977 Ethylene Substances 0.000 claims description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 5
- 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
- 125000003277 amino group Chemical group 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- 229920005604 random copolymer Polymers 0.000 claims description 3
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-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
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 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
- 239000007858 starting material Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 238000009210 therapy by ultrasound Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 1
- SURVUDPNZQGEJD-UHFFFAOYSA-N 1,4-diazepin-5-one Chemical compound O=C1C=CN=CC=N1 SURVUDPNZQGEJD-UHFFFAOYSA-N 0.000 claims 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 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 claims 1
- 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 claims 1
- 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 1
- 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 claims 1
- HPOKJLFNDLWVBS-UHFFFAOYSA-N 2-(3-ethyl-3,5,5-trimethyl-2-oxomorpholin-4-yl)oxy-2-methylpropanenitrile Chemical compound CCC1(C)N(OC(C)(C)C#N)C(C)(C)COC1=O HPOKJLFNDLWVBS-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- YOIPYKKWCRTZDK-UHFFFAOYSA-N 2-(6,6-diethyl-2,2,3,3-tetramethyl-5-oxopiperazin-1-yl)oxy-2-methylpropanenitrile Chemical compound CCC1(CC)N(OC(C)(C)C#N)C(C)(C)C(C)(C)NC1=O YOIPYKKWCRTZDK-UHFFFAOYSA-N 0.000 claims 1
- QPBROXAWPRPNFP-UHFFFAOYSA-N 3,3,5,5-tetramethyl-4-(1-phenylethoxy)morpholin-2-one Chemical compound C=1C=CC=CC=1C(C)ON1C(C)(C)COC(=O)C1(C)C QPBROXAWPRPNFP-UHFFFAOYSA-N 0.000 claims 1
- IEFBSBLICBWGLS-UHFFFAOYSA-N 3,3-diethyl-5,5-dimethyl-4-(1-phenylethoxy)-1-(2,4,4-trimethylpentan-2-yl)piperazin-2-one Chemical compound CC1(C)CN(C(C)(C)CC(C)(C)C)C(=O)C(CC)(CC)N1OC(C)C1=CC=CC=C1 IEFBSBLICBWGLS-UHFFFAOYSA-N 0.000 claims 1
- XHLBWNGWSDTRNY-UHFFFAOYSA-N 3-ethyl-3,5,5-trimethyl-4-(1-phenylethoxy)morpholin-2-one Chemical compound CC1(C)COC(=O)C(CC)(C)N1OC(C)C1=CC=CC=C1 XHLBWNGWSDTRNY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 1
- SYNHCENRCUAUNM-UHFFFAOYSA-N Nitrogen mustard N-oxide hydrochloride Chemical group Cl.ClCC[N+]([O-])(C)CCCl SYNHCENRCUAUNM-UHFFFAOYSA-N 0.000 claims 1
- 125000005396 acrylic acid ester group Chemical group 0.000 claims 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims 1
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 claims 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims 1
- 239000002324 mouth wash Substances 0.000 claims 1
- 229940051866 mouthwash Drugs 0.000 claims 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 102200160920 rs35304565 Human genes 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 abstract description 15
- 150000002367 halogens Chemical class 0.000 abstract description 15
- 150000003254 radicals Chemical class 0.000 abstract description 12
- 239000002243 precursor Substances 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 150000001412 amines Chemical class 0.000 abstract description 6
- 239000003999 initiator Substances 0.000 abstract description 6
- 150000001721 carbon Chemical group 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 abstract 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 130
- 238000006243 chemical reaction Methods 0.000 description 125
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 121
- 239000000243 solution Substances 0.000 description 99
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 75
- 230000002079 cooperative effect Effects 0.000 description 75
- 239000007788 liquid Substances 0.000 description 68
- 238000005227 gel permeation chromatography Methods 0.000 description 67
- 229910052786 argon Inorganic materials 0.000 description 65
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 63
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 52
- 238000003756 stirring Methods 0.000 description 36
- 238000005481 NMR spectroscopy Methods 0.000 description 35
- 239000012230 colorless oil Substances 0.000 description 31
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 30
- 238000004458 analytical method Methods 0.000 description 29
- 238000000921 elemental analysis Methods 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 239000000123 paper Substances 0.000 description 27
- 239000013078 crystal Substances 0.000 description 25
- 239000003921 oil Substances 0.000 description 25
- 125000000304 alkynyl group Chemical group 0.000 description 21
- 238000009826 distribution Methods 0.000 description 21
- 125000003342 alkenyl group Chemical group 0.000 description 20
- 125000003118 aryl group Chemical group 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 17
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 16
- 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
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 150000001335 aliphatic alkanes Chemical class 0.000 description 10
- 239000000463 material Substances 0.000 description 10
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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- 238000004587 chromatography analysis Methods 0.000 description 9
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- 230000015572 biosynthetic process Effects 0.000 description 8
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 150000007857 hydrazones Chemical class 0.000 description 8
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
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- 101100518501 Mus musculus Spp1 gene Proteins 0.000 description 7
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 7
- 230000008030 elimination Effects 0.000 description 7
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229940125782 compound 2 Drugs 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000007789 gas Substances 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
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 6
- 229910002651 NO3 Inorganic materials 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
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- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 238000009434 installation Methods 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 125000003884 phenylalkyl group Chemical group 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 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
- 239000010959 steel Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000006557 surface reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 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
- 150000003568 thioethers Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- BYQADQLDVPAGSR-UHFFFAOYSA-N toluene;hydrobromide Chemical compound Br.CC1=CC=CC=C1 BYQADQLDVPAGSR-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 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
- 229910052722 tritium Inorganic materials 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004260 weight control Methods 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)
- 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)
Applications Claiming Priority (1)
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| EP98811030 | 1998-10-16 |
Publications (1)
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| TWI225483B true TWI225483B (en) | 2004-12-21 |
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| TW088115002A TWI225483B (en) | 1998-10-16 | 1999-08-30 | Heterocyclic alkoxyamines as regulators in controlled radical polymerization process |
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| KR (1) | KR100597892B1 (enExample) |
| CN (1) | CN100343285C (enExample) |
| AU (1) | AU769061B2 (enExample) |
| BE (1) | BE1012727A5 (enExample) |
| BR (1) | BR9904685A (enExample) |
| CA (1) | CA2286375A1 (enExample) |
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| 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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| EP1189875B1 (en) * | 1999-07-02 | 2004-08-04 | Ciba SC Holding AG | 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 |
| EP1655303B1 (en) * | 2000-05-19 | 2011-02-23 | Basf Se | Process for the Controlled Increase in Molecular Weight of Polyethylene or Polyethylene Blends |
| 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 |
| 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 |
| 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 |
| 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 |
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| WO2008032732A1 (en) * | 2006-09-15 | 2008-03-20 | Kuraray Co., Ltd. | Methacrylic resin composition, resin modifier, and molded body |
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| 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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| EP2385937A1 (en) * | 2009-01-08 | 2011-11-16 | Basf Se | Polymerisation initiator |
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| US9790452B2 (en) | 2013-03-27 | 2017-10-17 | Basf Se | Block copolymers as soil release agents in laundry processes |
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| 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 |
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| DE102019219166B4 (de) | 2019-12-09 | 2023-08-24 | Tesa Se | Strukturelle Haftklebemasse und ihre Verwendung |
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| 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 |
-
1999
- 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 AU AU53617/99A patent/AU769061B2/en not_active Ceased
- 1999-10-12 BE BE9900673A patent/BE1012727A5/fr not_active IP Right Cessation
- 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 ES ES009902254A patent/ES2178908B1/es not_active Expired - Fee Related
- 1999-10-14 KR KR1019990044561A patent/KR100597892B1/ko not_active Expired - Fee Related
- 1999-10-14 US US09/417,538 patent/US6479608B1/en not_active Expired - Lifetime
- 1999-10-14 FR FR9912810A patent/FR2784684B1/fr not_active Expired - Lifetime
- 1999-10-14 CA CA002286375A patent/CA2286375A1/en not_active Abandoned
- 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
-
2002
- 2002-07-09 US US10/191,193 patent/US6664353B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| 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 |
| JP4895416B2 (ja) | 2012-03-14 |
| 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 |
| KR100597892B1 (ko) | 2006-07-06 |
| SE9903593L (sv) | 2000-04-17 |
| FR2784684B1 (fr) | 2001-01-26 |
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