DE69933020T2 - Nitroxyl Derivate mit Glycidyl- oder Alkylcarbonylgruppen als Initiatoren für Radikalpolymerisationen - Google Patents
Nitroxyl Derivate mit Glycidyl- oder Alkylcarbonylgruppen als Initiatoren für Radikalpolymerisationen Download PDFInfo
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- DE69933020T2 DE69933020T2 DE69933020T DE69933020T DE69933020T2 DE 69933020 T2 DE69933020 T2 DE 69933020T2 DE 69933020 T DE69933020 T DE 69933020T DE 69933020 T DE69933020 T DE 69933020T DE 69933020 T2 DE69933020 T2 DE 69933020T2
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- oligomer
- monomer
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- 239000003999 initiator Substances 0.000 title claims description 30
- 238000010526 radical polymerization reaction Methods 0.000 title claims description 14
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 title description 15
- 125000004448 alkyl carbonyl group Chemical group 0.000 title description 8
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical class O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 title description 6
- 239000000178 monomer Substances 0.000 claims description 61
- 229920000642 polymer Polymers 0.000 claims description 45
- 238000006116 polymerization reaction Methods 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 26
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 24
- 150000003254 radicals Chemical class 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 18
- 229920001400 block copolymer Polymers 0.000 claims description 11
- 229920001577 copolymer Polymers 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 7
- 238000003776 cleavage reaction Methods 0.000 claims description 6
- 150000001993 dienes Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 230000007017 scission Effects 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- SYNHCENRCUAUNM-UHFFFAOYSA-N Nitrogen mustard N-oxide hydrochloride Chemical group Cl.ClCC[N+]([O-])(C)CCCl SYNHCENRCUAUNM-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005262 alkoxyamine group Chemical group 0.000 claims description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003926 acrylamides Chemical class 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 230000005670 electromagnetic radiation Effects 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 230000000379 polymerizing effect Effects 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
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- -1 Allylalkohl Chemical compound 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229920000578 graft copolymer Polymers 0.000 description 5
- 229920002521 macromolecule Polymers 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000006184 cosolvent Substances 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZPINEGNTNFBSEK-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-[1-[4-(oxiran-2-ylmethoxy)phenyl]ethoxy]-4-propoxypiperidine Chemical compound CC1(C)CC(OCCC)CC(C)(C)N1OC(C)C(C=C1)=CC=C1OCC1OC1 ZPINEGNTNFBSEK-UHFFFAOYSA-N 0.000 description 3
- KSIFCIGYWZLLRY-UHFFFAOYSA-N 2-[(2-ethylphenoxy)methyl]oxirane Chemical compound CCC1=CC=CC=C1OCC1OC1 KSIFCIGYWZLLRY-UHFFFAOYSA-N 0.000 description 3
- AQKZSTFCPAOFIV-UHFFFAOYSA-N 2-[(4-ethylphenoxy)methyl]oxirane Chemical compound C1=CC(CC)=CC=C1OCC1OC1 AQKZSTFCPAOFIV-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 3
- 229920006030 multiblock copolymer Polymers 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229920002959 polymer blend Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 2
- IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 2
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229920003244 diene elastomer Polymers 0.000 description 2
- 238000007323 disproportionation reaction Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
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- 239000000284 extract Substances 0.000 description 2
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- 150000008282 halocarbons Chemical class 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
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- 125000005395 methacrylic acid group Chemical class 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- NODGRWCMFMEGJH-UHFFFAOYSA-N p-ethylacetophenone Chemical compound CCC1=CC=C(C(C)=O)C=C1 NODGRWCMFMEGJH-UHFFFAOYSA-N 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- 150000003839 salts Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000001542 size-exclusion chromatography Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
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- LMQJZPNTLDBCHC-UHFFFAOYSA-N 1,1,3,3-tetraethyl-2h-isoindole Chemical compound C1=CC=C2C(CC)(CC)NC(CC)(CC)C2=C1 LMQJZPNTLDBCHC-UHFFFAOYSA-N 0.000 description 1
- WNGJCVHWVCNYHU-UHFFFAOYSA-N 1,1,3,3-tetrapropyl-2h-isoindole Chemical compound C1=CC=C2C(CCC)(CCC)NC(CCC)(CCC)C2=C1 WNGJCVHWVCNYHU-UHFFFAOYSA-N 0.000 description 1
- YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical compound CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 description 1
- FGDZIAMRHXEPLG-UHFFFAOYSA-N 1,2,2,3-tetramethylpyrrolidine Chemical compound CC1CCN(C)C1(C)C FGDZIAMRHXEPLG-UHFFFAOYSA-N 0.000 description 1
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
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- 229920000359 diblock copolymer Polymers 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
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- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Polymerization Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Paper (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98810194 | 1998-03-09 | ||
| EP98810194 | 1998-03-09 | ||
| PCT/EP1999/001233 WO1999046261A1 (en) | 1998-03-09 | 1999-02-26 | Nitroxyl derivatives with glycidyl or alkylcarbonyl groups as initiators for radical polymerisation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69933020D1 DE69933020D1 (de) | 2006-10-12 |
| DE69933020T2 true DE69933020T2 (de) | 2007-04-05 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69933020T Expired - Lifetime DE69933020T2 (de) | 1998-03-09 | 1999-02-26 | Nitroxyl Derivate mit Glycidyl- oder Alkylcarbonylgruppen als Initiatoren für Radikalpolymerisationen |
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| Country | Link |
|---|---|
| US (1) | US6566468B1 (https=) |
| EP (1) | EP1071681B1 (https=) |
| JP (1) | JP4584448B2 (https=) |
| AU (1) | AU2929699A (https=) |
| CA (1) | CA2321792C (https=) |
| DE (1) | DE69933020T2 (https=) |
| TW (1) | TW495515B (https=) |
| WO (1) | WO1999046261A1 (https=) |
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| TWI225483B (en) * | 1998-10-16 | 2004-12-21 | Ciba Sc Holding Ag | Heterocyclic alkoxyamines as regulators in controlled radical polymerization process |
| US6472486B2 (en) | 1999-03-09 | 2002-10-29 | Symyx Technologies, Inc. | Controlled stable free radical emulsion polymerization processes |
| AU3733800A (en) | 1999-03-09 | 2000-09-28 | Symyx Technologies, Inc. | Controlled free radical emulsion and water-based polymerizations and seeded methodologies |
| JP4829447B2 (ja) * | 1999-07-02 | 2011-12-07 | チバ ホールディング インコーポレーテッド | 官能化されたマクロマーの製造のための１および多官能価アルコキシアミン |
| US6716948B1 (en) | 1999-07-31 | 2004-04-06 | Symyx Technologies, Inc. | Controlled-architecture polymers and use thereof as separation media |
| AU6279900A (en) | 1999-08-12 | 2001-03-13 | Ciba Specialty Chemicals Holding Inc. | Polymer blends with improved impact resistance |
| TW546311B (en) | 1999-11-25 | 2003-08-11 | Ciba Sc Holding Ag | Composition and method for color improvement of nitroxyl containing polymers |
| JP2001253916A (ja) * | 2000-03-10 | 2001-09-18 | Nippon Chem Ind Co Ltd | フルオロアルキル基含有ホスホン酸オリゴマー類およびその製造方法、並びにその用途 |
| TW572896B (en) * | 2000-05-26 | 2004-01-21 | Ciba Sc Holding Ag | Process for the synthesis of amine ethers from secondary amino oxides |
| US20030031675A1 (en) | 2000-06-06 | 2003-02-13 | Mikesell Glen E. | B7-related nucleic acids and polypeptides useful for immunomodulation |
| TWI274053B (en) * | 2000-12-14 | 2007-02-21 | Ciba Sc Holding Ag | N-alkoxy-4,4-dioxy-polyalkyl-piperidine compounds, with glycidyl or alkylcarbonyl groups as functional initiators for controlled radical polymerization |
| US6544304B2 (en) | 2001-04-02 | 2003-04-08 | Ciba Specialty Chemicals Corporation | Candle wax stabilized with morpholinones |
| US7868171B2 (en) * | 2001-11-12 | 2011-01-11 | Ciba Specialty Chemicals Corp. | N-alkoxy-4, 4-dioxy-polyalkyl-piperidines as radical polymerization initiators |
| US7144691B2 (en) | 2002-03-05 | 2006-12-05 | Ciba Specialty Chemicals Corporation | Color photographic recording material |
| AU2003267011A1 (en) * | 2002-09-04 | 2004-03-29 | Ciba Specialty Chemicals Holding Inc. | Method of producing comb or star copolymers using epoxy-functionalized nitroxylethers |
| CA2496989A1 (en) | 2002-09-26 | 2004-04-08 | Ciba Specialty Chemicals Holding Inc. | Thermoplastic compositions with enhanced melt flow and compatibility |
| WO2004069887A2 (en) * | 2003-02-10 | 2004-08-19 | Ciba Specialty Chemicals Holding Inc. | Comb copolymers with defined side chains and process for their manufacture |
| US6967228B2 (en) | 2003-05-01 | 2005-11-22 | Firestone Polymers, Llc | Stable free radical polymers |
| US20060079624A1 (en) * | 2004-10-08 | 2006-04-13 | Hildeberto Nava | Crosslinkable polymer systems |
| US20060173142A1 (en) * | 2005-02-01 | 2006-08-03 | Hildeberto Nava | Functionalized thermosetting resin systems |
| US20090299013A1 (en) * | 2005-04-04 | 2009-12-03 | Jochen Fink | Process for the Preparation of Star and Block-Copolymers Via Epoxy-Functionalized Alkoxyamines |
| US7279527B2 (en) | 2005-04-22 | 2007-10-09 | Bridgestone Corporation | Method of converting anionic living end to protected free radical living end and applications thereof |
| US20100311920A1 (en) * | 2005-08-26 | 2010-12-09 | Cid Centro De Investigacion Y Desarrollo Tecnologico Sa De Cv | Using Reactive Block Copolymers as Chain Extenders and Surface Modifiers |
| US8357759B2 (en) * | 2005-08-26 | 2013-01-22 | CID Centro de Investigación y Desarrollo Tecnológico S.A. de C.V. | Reactive block copolymers |
| EP2038701B1 (en) | 2006-07-06 | 2017-04-12 | Basf Se | Encapsulated dispersions comprising electrophoretically mobile organic colorants |
| US20100311849A1 (en) * | 2006-08-23 | 2010-12-09 | Cid Centro De Investigacion Y Desarrollo Tecnologico Sa De Cv | Using Reactive Block Copolymers as Chain Extenders and Surface Modifiers |
| US7985826B2 (en) | 2006-12-22 | 2011-07-26 | Reichhold, Inc. | Molding resins using renewable resource component |
| US7560509B2 (en) | 2006-12-29 | 2009-07-14 | Bridgestone Corporation | Method of directing grafting by controlling the location of high vinyl segments in a polymer |
| US7396887B1 (en) | 2006-12-29 | 2008-07-08 | Bridgestone Corporation | Insitu removal of chelator from anionic polymerization reactions |
| US7737218B2 (en) | 2006-12-29 | 2010-06-15 | Bridgestone Corporation | Method for generating free radical capable polymers using tin or silicon halide compounds |
| US8030410B2 (en) | 2006-12-29 | 2011-10-04 | Bridgestone Corporation | Method for generating free radical capable polymers using carbonyl-containing compounds |
| US8270063B2 (en) | 2007-09-07 | 2012-09-18 | Basf Se | Encapsulated dispersions comprising electrophoretically mobile organic colorants |
| CN106699639A (zh) * | 2016-12-22 | 2017-05-24 | 甘肃省化工研究院 | 一种光稳定剂hs‑112的合成方法 |
| US11917906B2 (en) * | 2018-11-05 | 2024-02-27 | Merck Patent Gmbh | Compounds that can be used in an organic electronic device |
| FR3152278A1 (fr) | 2023-08-24 | 2025-02-28 | Snf Sa | polymère hydrosoluble ramifié comme liant pour batterie |
| FR3152279A1 (fr) | 2023-08-24 | 2025-02-28 | Snf Sa | Polymere hydrosoluble comme liant pour batterie |
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| JPS6089452A (ja) * | 1983-07-11 | 1985-05-20 | コモンウエルス サイエンテイフイツク アンド インダストリアル リサ−チ オ−ガニゼ−シヨン | 遊離基重合開始用化合物 |
| AU571240B2 (en) * | 1983-07-11 | 1988-04-14 | Commonwealth Scientific And Industrial Research Organisation | Alkoxy-amines, useful as initiators |
| EP0155912A3 (de) * | 1984-03-20 | 1986-06-04 | Ciba-Geigy Ag | Strahlenstabilisierte polymere Zusammensetzungen |
| TW270131B (https=) | 1993-07-13 | 1996-02-11 | Ciba Geigy | |
| HU220138B (hu) * | 1996-03-29 | 2001-11-28 | The Dow Chemical Co. | Szabadgyökös tömbpolimerizálási eljárás kaucsukkal módosított polimerek vinil-aromás monomerekből való előállítására |
| AU4773997A (en) | 1996-09-25 | 1998-04-17 | Akzo Nobel N.V. | No-compounds for pseudo-living radical polymerization |
| TWI225483B (en) * | 1998-10-16 | 2004-12-21 | Ciba Sc Holding Ag | Heterocyclic alkoxyamines as regulators in controlled radical polymerization process |
-
1999
- 1999-01-18 TW TW088100735A patent/TW495515B/zh not_active IP Right Cessation
- 1999-02-26 WO PCT/EP1999/001233 patent/WO1999046261A1/en not_active Ceased
- 1999-02-26 EP EP99910286A patent/EP1071681B1/en not_active Expired - Lifetime
- 1999-02-26 CA CA002321792A patent/CA2321792C/en not_active Expired - Fee Related
- 1999-02-26 AU AU29296/99A patent/AU2929699A/en not_active Abandoned
- 1999-02-26 JP JP2000535640A patent/JP4584448B2/ja not_active Expired - Fee Related
- 1999-02-26 US US09/623,547 patent/US6566468B1/en not_active Expired - Fee Related
- 1999-02-26 DE DE69933020T patent/DE69933020T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999046261A1 (en) | 1999-09-16 |
| AU2929699A (en) | 1999-09-27 |
| TW495515B (en) | 2002-07-21 |
| CA2321792A1 (en) | 1999-09-16 |
| JP4584448B2 (ja) | 2010-11-24 |
| JP2002506070A (ja) | 2002-02-26 |
| US6566468B1 (en) | 2003-05-20 |
| CA2321792C (en) | 2009-12-29 |
| EP1071681A1 (en) | 2001-01-31 |
| EP1071681B1 (en) | 2006-08-30 |
| DE69933020D1 (de) | 2006-10-12 |
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| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: CIBA HOLDING INC., BASEL, CH |
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| 8328 | Change in the person/name/address of the agent |
Representative=s name: MAIWALD PATENTANWALTSGESELLSCHAFT MBH, 80335 MUENC |