CA2264460A1 - 1-alkoxy-polyalkyl-piperidine derivatives and their use as polymerization regulators - Google Patents
1-alkoxy-polyalkyl-piperidine derivatives and their use as polymerization regulators Download PDFInfo
- Publication number
- CA2264460A1 CA2264460A1 CA002264460A CA2264460A CA2264460A1 CA 2264460 A1 CA2264460 A1 CA 2264460A1 CA 002264460 A CA002264460 A CA 002264460A CA 2264460 A CA2264460 A CA 2264460A CA 2264460 A1 CA2264460 A1 CA 2264460A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- group
- hydrogen
- phenyl
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 71
- 239000000178 monomer Substances 0.000 claims abstract description 98
- 150000001875 compounds Chemical class 0.000 claims abstract description 93
- 150000003254 radicals Chemical class 0.000 claims abstract description 58
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 54
- 239000000203 mixture Substances 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 29
- 239000003999 initiator Substances 0.000 claims abstract description 22
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 15
- 230000000977 initiatory effect Effects 0.000 claims abstract description 10
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 5
- -1 aromatic tricarboxylic acid Chemical class 0.000 claims description 78
- 229910052739 hydrogen Inorganic materials 0.000 claims description 65
- 239000001257 hydrogen Substances 0.000 claims description 60
- 229910052799 carbon Inorganic materials 0.000 claims description 58
- 125000004432 carbon atom Chemical group C* 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 47
- 229920000642 polymer Polymers 0.000 claims description 47
- 150000002431 hydrogen Chemical class 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 25
- 125000001931 aliphatic group Chemical group 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 20
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 14
- 229920001577 copolymer Polymers 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 238000010526 radical polymerization reaction Methods 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 9
- PPGAFAOTXHZHCA-UHFFFAOYSA-N 2-methylpropanenitrile Chemical compound C[C](C)C#N PPGAFAOTXHZHCA-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 6
- 238000010504 bond cleavage reaction Methods 0.000 claims description 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 230000007017 scission Effects 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000006839 xylylene group Chemical group 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 claims description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-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
- FLCAEMBIQVZWIF-UHFFFAOYSA-N 6-(dimethylamino)-2-methylhex-2-enamide Chemical compound CN(C)CCCC=C(C)C(N)=O FLCAEMBIQVZWIF-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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- SYNHCENRCUAUNM-UHFFFAOYSA-N Nitrogen mustard N-oxide hydrochloride Chemical group Cl.ClCC[N+]([O-])(C)CCCl SYNHCENRCUAUNM-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003926 acrylamides Chemical class 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical class C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 150000008360 acrylonitriles Chemical class 0.000 claims description 2
- 125000005250 alkyl acrylate group Chemical group 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
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims description 2
- 230000005670 electromagnetic radiation Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 2
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical class C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 150000003440 styrenes Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 238000009210 therapy by ultrasound Methods 0.000 claims description 2
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 15
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 2
- 125000003031 C5-C7 cycloalkylene group Chemical group 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 60
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 34
- 229910052786 argon Inorganic materials 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000005227 gel permeation chromatography Methods 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 238000000921 elemental analysis Methods 0.000 description 23
- 239000007788 liquid Substances 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 238000004440 column chromatography Methods 0.000 description 15
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 15
- 230000008020 evaporation Effects 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
- 229960001866 silicon dioxide Drugs 0.000 description 14
- 229920001400 block copolymer Polymers 0.000 description 13
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000284 extract Substances 0.000 description 12
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 11
- 235000019400 benzoyl peroxide Nutrition 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 239000004342 Benzoyl peroxide Substances 0.000 description 10
- 229960003328 benzoyl peroxide Drugs 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 9
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 239000012530 fluid Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 239000006184 cosolvent Substances 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- TUOLXKNMFCOMGN-UHFFFAOYSA-N 2,6-diethyl-2,3,6-trimethylpiperidin-4-one Chemical compound CCC1(C)CC(=O)C(C)C(C)(CC)N1 TUOLXKNMFCOMGN-UHFFFAOYSA-N 0.000 description 5
- 229910052684 Cerium Inorganic materials 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229920000578 graft copolymer Polymers 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- ZBXMSPIJFSLZIP-UHFFFAOYSA-N 2,2,6-trimethyl-6-propan-2-ylpiperidin-4-one Chemical compound CC(C)C1(C)CC(=O)CC(C)(C)N1 ZBXMSPIJFSLZIP-UHFFFAOYSA-N 0.000 description 3
- SKTJKGMWKIKKGI-UHFFFAOYSA-N 2,2-diethyl-6,6-dimethylpiperidin-4-ol Chemical compound CCC1(CC)CC(O)CC(C)(C)N1 SKTJKGMWKIKKGI-UHFFFAOYSA-N 0.000 description 3
- TUGPREKSTXAQBY-UHFFFAOYSA-N 2,6-diethyl-2,3,6-trimethylpiperidin-4-ol Chemical compound CCC1(C)CC(O)C(C)C(C)(CC)N1 TUGPREKSTXAQBY-UHFFFAOYSA-N 0.000 description 3
- GMTUHHKHSXQNQN-UHFFFAOYSA-N 2-ethyl-2,6,6-trimethylpiperidine Chemical compound CCC1(C)CCCC(C)(C)N1 GMTUHHKHSXQNQN-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 3
- CCPHAMSKHBDMDS-UHFFFAOYSA-N Chetoseminudin B Natural products C=1NC2=CC=CC=C2C=1CC1(SC)NC(=O)C(CO)(SC)N(C)C1=O CCPHAMSKHBDMDS-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229920002959 polymer blend Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- CRRUGYDDEMGVDY-UHFFFAOYSA-N 1-bromoethylbenzene Chemical compound CC(Br)C1=CC=CC=C1 CRRUGYDDEMGVDY-UHFFFAOYSA-N 0.000 description 2
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- MLTZSDWBQJMQBY-UHFFFAOYSA-N 2,2-diethyl-6,6-dimethyl-1-(1-phenylethoxy)piperidin-4-ol Chemical compound CCC1(CC)CC(O)CC(C)(C)N1OC(C)C1=CC=CC=C1 MLTZSDWBQJMQBY-UHFFFAOYSA-N 0.000 description 2
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical group OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical compound CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- DGSTWPUWTGYKAY-UHFFFAOYSA-N 2,6-diethyl-2,3,6-trimethyl-1-(1-phenylethoxy)piperidin-4-ol Chemical compound CCC1(C)CC(O)C(C)C(C)(CC)N1OC(C)C1=CC=CC=C1 DGSTWPUWTGYKAY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZPZGJOJXYBBSBX-UHFFFAOYSA-N 2-(2-ethyl-4-hydroxy-2,6,6-trimethylpiperidin-1-yl)oxy-2-methylpropanenitrile Chemical compound CCC1(C)CC(O)CC(C)(C)N1OC(C)(C)C#N ZPZGJOJXYBBSBX-UHFFFAOYSA-N 0.000 description 2
- JTGQUPMVZHVAMK-UHFFFAOYSA-N 2-ethyl-2,6,6-trimethyl-1-(1-phenylethoxy)piperidin-4-ol Chemical compound CCC1(C)CC(O)CC(C)(C)N1OC(C)C1=CC=CC=C1 JTGQUPMVZHVAMK-UHFFFAOYSA-N 0.000 description 2
- JCBSYOKILZXFLZ-UHFFFAOYSA-N 2-ethyl-2,6,6-trimethylpiperidin-4-one Chemical compound CCC1(C)CC(=O)CC(C)(C)N1 JCBSYOKILZXFLZ-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 2
- FJJUREOQLBHJDY-UHFFFAOYSA-N 3-ethyl-2,6-dimethyl-2,6-dipropylpiperidin-4-one Chemical compound CCCC1(C)CC(=O)C(CC)C(C)(CCC)N1 FJJUREOQLBHJDY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 2
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BHMWILJWBTXHBP-UHFFFAOYSA-N [2,2-diethyl-6,6-dimethyl-1-(1-phenylethoxy)piperidin-4-yl] benzoate Chemical compound CCC1(CC)CC(OC(=O)C=2C=CC=CC=2)CC(C)(C)N1OC(C)C1=CC=CC=C1 BHMWILJWBTXHBP-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000005262 alkoxyamine group Chemical group 0.000 description 2
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 229920000359 diblock copolymer Polymers 0.000 description 2
- 238000007323 disproportionation reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- GKCPCPKXFGQXGS-UHFFFAOYSA-N ditert-butyldiazene Chemical compound CC(C)(C)N=NC(C)(C)C GKCPCPKXFGQXGS-UHFFFAOYSA-N 0.000 description 2
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229940093499 ethyl acetate Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 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 2
- 239000003973 paint Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000002952 polymeric resin Substances 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000001542 size-exclusion chromatography Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 229920000428 triblock copolymer Polymers 0.000 description 2
- 150000003672 ureas Chemical group 0.000 description 2
- PCJGHYSTCBLKIA-UHFFFAOYSA-N (1-acetylcyclohexyl)sulfonyloxy 1-acetylcyclohexane-1-sulfonate Chemical compound C1CCCCC1(C(C)=O)S(=O)(=O)OOS(=O)(=O)C1(C(=O)C)CCCCC1 PCJGHYSTCBLKIA-UHFFFAOYSA-N 0.000 description 1
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
- ZICNIEOYWVIEQJ-UHFFFAOYSA-N (2-methylbenzoyl) 2-methylbenzenecarboperoxoate Chemical compound CC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1C ZICNIEOYWVIEQJ-UHFFFAOYSA-N 0.000 description 1
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
- OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 description 1
- 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
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 1
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 description 1
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004958 1,4-naphthylene group Chemical group 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- XSZYESUNPWGWFQ-UHFFFAOYSA-N 1-(2-hydroperoxypropan-2-yl)-4-methylcyclohexane Chemical compound CC1CCC(C(C)(C)OO)CC1 XSZYESUNPWGWFQ-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
- FMRWQLAJBBKXDM-UHFFFAOYSA-N 2,2,5,5-tetramethylpyrrolidine Chemical compound CC1(C)CCC(C)(C)N1 FMRWQLAJBBKXDM-UHFFFAOYSA-N 0.000 description 1
- HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-UHFFFAOYSA-N 0.000 description 1
- BPAVPPMLBNUUIR-UHFFFAOYSA-N 2,2-diethyl-6,6-dimethylpiperidin-4-one Chemical compound CCC1(CC)CC(=O)CC(C)(C)N1 BPAVPPMLBNUUIR-UHFFFAOYSA-N 0.000 description 1
- 125000004825 2,2-dimethylpropylene group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[*:1])C([H])([H])[*:2] 0.000 description 1
- WUKNSAYHZNWXQZ-UHFFFAOYSA-N 2,6-diethyl-2,3,6-trimethoxy-1-phenylmethoxypiperidine Chemical compound CCC1(OC)CCC(OC)C(CC)(OC)N1OCC1=CC=CC=C1 WUKNSAYHZNWXQZ-UHFFFAOYSA-N 0.000 description 1
- XNTBMMKNLWUKDH-UHFFFAOYSA-N 2,6-diethyl-2,3,6-trimethyl-1-(1-phenylethoxy)piperidin-4-one Chemical compound CCC1(C)CC(=O)C(C)C(C)(CC)N1OC(C)C1=CC=CC=C1 XNTBMMKNLWUKDH-UHFFFAOYSA-N 0.000 description 1
- HPJYHSTXYGSXDT-UHFFFAOYSA-N 2,6-diethyl-2,3,6-trimethyl-1-[(2-methylpropan-2-yl)oxy]piperidin-4-one Chemical compound CCC1(C)CC(=O)C(C)C(C)(CC)N1OC(C)(C)C HPJYHSTXYGSXDT-UHFFFAOYSA-N 0.000 description 1
- CCTFAOUOYLVUFG-UHFFFAOYSA-N 2-(1-amino-1-imino-2-methylpropan-2-yl)azo-2-methylpropanimidamide Chemical compound NC(=N)C(C)(C)N=NC(C)(C)C(N)=N CCTFAOUOYLVUFG-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 1
- ZWVQTJSKEYKPKW-UHFFFAOYSA-N 2-(2-ethyl-2,6,6-trimethylpiperidin-1-yl)oxy-2-methylpropanenitrile Chemical compound CCC1(C)CCCC(C)(C)N1OC(C)(C)C#N ZWVQTJSKEYKPKW-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- QSFTWOJPCWPORR-UHFFFAOYSA-N 2-(2-tert-butylperoxypropan-2-ylperoxy)-2-methylpropane Chemical compound CC(C)(C)OOC(C)(C)OOC(C)(C)C QSFTWOJPCWPORR-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- OALMZWNBNXQUAL-UHFFFAOYSA-N 2-[(1-amino-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanamide Chemical compound NC(=O)C(C)(C)N=NC(C)(C)C(N)=O OALMZWNBNXQUAL-UHFFFAOYSA-N 0.000 description 1
- PFHOSZAOXCYAGJ-UHFFFAOYSA-N 2-[(2-cyano-4-methoxy-4-methylpentan-2-yl)diazenyl]-4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)(C)OC PFHOSZAOXCYAGJ-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- LIZVXGBYTGTTTI-UHFFFAOYSA-N 2-[(4-methylphenyl)sulfonylamino]-2-phenylacetic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(C(O)=O)C1=CC=CC=C1 LIZVXGBYTGTTTI-UHFFFAOYSA-N 0.000 description 1
- CKSAKVMRQYOFBC-UHFFFAOYSA-N 2-cyanopropan-2-yliminourea Chemical compound N#CC(C)(C)N=NC(N)=O CKSAKVMRQYOFBC-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- WRFRKEDTRYVQOV-UHFFFAOYSA-N 2-methyl-2-(2,2,6-trimethyl-4-oxo-6-propan-2-ylpiperidin-1-yl)oxypropanenitrile Chemical compound CC(C)C1(C)CC(=O)CC(C)(C)N1OC(C)(C)C#N WRFRKEDTRYVQOV-UHFFFAOYSA-N 0.000 description 1
- HXLKMVIDJLRHNN-UHFFFAOYSA-N 2-methyl-2-(2,2,6-trimethyl-4-oxo-6-propan-2-ylpiperidin-1-yl)propanenitrile Chemical compound CC(C)C1(C)CC(=O)CC(C)(C)N1C(C)(C)C#N HXLKMVIDJLRHNN-UHFFFAOYSA-N 0.000 description 1
- JJRDRFZYKKFYMO-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-ylperoxy)butane Chemical compound CCC(C)(C)OOC(C)(C)CC JJRDRFZYKKFYMO-UHFFFAOYSA-N 0.000 description 1
- QRIQYQXNFSXNGR-UHFFFAOYSA-N 3,3,6,6,9,9-hexamethyl-1,2,4,5-tetraoxonane Chemical compound CC1(C)CCC(C)(C)OOC(C)(C)OO1 QRIQYQXNFSXNGR-UHFFFAOYSA-N 0.000 description 1
- MUAFAOUCQHXNNH-UHFFFAOYSA-N 3,5-bis(tert-butylperoxy)-3,5-dimethyldioxolane Chemical compound CC(C)(C)OOC1(C)CC(C)(OOC(C)(C)C)OO1 MUAFAOUCQHXNNH-UHFFFAOYSA-N 0.000 description 1
- YUHONZLMSQQDQT-UHFFFAOYSA-N 3,7-dimethyloctyl 2-pyrrolidin-1-ylacetate Chemical compound CC(C)CCCC(C)CCOC(=O)CN1CCCC1 YUHONZLMSQQDQT-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- JJHHIGCUQPTUHO-UHFFFAOYSA-N 3-tert-butylperoxy-3-phenyl-2-benzofuran-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(OOC(C)(C)C)C1=CC=CC=C1 JJHHIGCUQPTUHO-UHFFFAOYSA-N 0.000 description 1
- MKTOIPPVFPJEQO-UHFFFAOYSA-N 4-(3-carboxypropanoylperoxy)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OOC(=O)CCC(O)=O MKTOIPPVFPJEQO-UHFFFAOYSA-N 0.000 description 1
- OPPHXULEHGYZRW-UHFFFAOYSA-N 4-methoxy-2,4-dimethyl-2-phenyldiazenylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC1=CC=CC=C1 OPPHXULEHGYZRW-UHFFFAOYSA-N 0.000 description 1
- FKAJZOZTZXQGTJ-UHFFFAOYSA-N 5,5-dimethyl-1,3-diazabicyclo[2.2.0]hex-3-ene Chemical compound C1N2C(C1(C)C)=NC2 FKAJZOZTZXQGTJ-UHFFFAOYSA-N 0.000 description 1
- XKXGWYAQJRXDPI-UHFFFAOYSA-N 7-methyloctanoyl 7-methyloctaneperoxoate Chemical compound CC(C)CCCCCC(=O)OOC(=O)CCCCCC(C)C XKXGWYAQJRXDPI-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000005011 alkyl ether group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- WPKWPKDNOPEODE-UHFFFAOYSA-N bis(2,4,4-trimethylpentan-2-yl)diazene Chemical compound CC(C)(C)CC(C)(C)N=NC(C)(C)CC(C)(C)C WPKWPKDNOPEODE-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- GGAUUQHSCNMCAU-UHFFFAOYSA-N butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)C(C(O)=O)CC(O)=O GGAUUQHSCNMCAU-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000003651 hexanedioyl group Chemical group C(CCCCC(=O)*)(=O)* 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000012690 ionic polymerization Methods 0.000 description 1
- 125000006229 isopropoxyethyl group Chemical group [H]C([H])([H])C([H])(OC([H])([H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])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
- 239000010985 leather Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000003099 maleoyl group Chemical group C(\C=C/C(=O)*)(=O)* 0.000 description 1
- 125000000346 malonyl group Chemical group C(CC(=O)*)(=O)* 0.000 description 1
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 1
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229920006030 multiblock copolymer Polymers 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
- VXRNYQMFDGOGSI-UHFFFAOYSA-N n-(1,3-dihydroxy-2-methylpropan-2-yl)-2-[[1-[(1,3-dihydroxy-2-methylpropan-2-yl)amino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCC(C)(CO)NC(=O)C(C)(C)N=NC(C)(C)C(=O)NC(C)(CO)CO VXRNYQMFDGOGSI-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-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
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 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
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 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
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 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
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940038597 peroxide anti-acne preparations for topical use Drugs 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 230000000704 physical effect Effects 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
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920005553 polystyrene-acrylate Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-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
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 102220044832 rs587781608 Human genes 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000013341 scale-up Methods 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
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])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
- 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
- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- KHJNXCATZZIGAX-UHFFFAOYSA-N tert-butyl 2-ethyl-2-methylheptaneperoxoate Chemical compound CCCCCC(C)(CC)C(=O)OOC(C)(C)C KHJNXCATZZIGAX-UHFFFAOYSA-N 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 1
- 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
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 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
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000012745 toughening agent Substances 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 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
- 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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- 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
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)
- Hydrogenated Pyridines (AREA)
- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98810194 | 1998-03-09 | ||
| EP98810194.5 | 1998-03-09 | ||
| EP98810531 | 1998-06-11 | ||
| EP98810531.8 | 1998-06-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2264460A1 true CA2264460A1 (en) | 1999-09-09 |
Family
ID=26151881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002264460A Abandoned CA2264460A1 (en) | 1998-03-09 | 1999-03-05 | 1-alkoxy-polyalkyl-piperidine derivatives and their use as polymerization regulators |
Country Status (18)
| Country | Link |
|---|---|
| US (4) | US6353107B1 (https=) |
| JP (1) | JP4651137B2 (https=) |
| KR (1) | KR100581654B1 (https=) |
| CN (1) | CN1171871C (https=) |
| AT (1) | AT408655B (https=) |
| AU (1) | AU754927B2 (https=) |
| BE (1) | BE1012399A3 (https=) |
| BR (1) | BR9900977B1 (https=) |
| CA (1) | CA2264460A1 (https=) |
| CH (1) | CH693416A5 (https=) |
| CZ (1) | CZ78999A3 (https=) |
| DE (1) | DE19909767B4 (https=) |
| ES (1) | ES2155014B1 (https=) |
| FR (1) | FR2777892B1 (https=) |
| GB (1) | GB2335190B (https=) |
| IT (1) | IT1309590B1 (https=) |
| NL (1) | NL1011493C2 (https=) |
| SG (1) | SG82601A1 (https=) |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG82601A1 (en) * | 1998-03-09 | 2001-08-21 | Ciba Sc Holding Ag | 1-alkoxy-polyalkyl-piperidine derivatives and their use as polymerization regulators |
| US6518326B1 (en) * | 1998-07-31 | 2003-02-11 | Ciba Specialty Chemicals Corporation | Open chain alkoxyamine compounds and their use as polymerization regulators |
| EP1119585B1 (fr) | 1998-10-06 | 2004-06-16 | Atofina | Procede de polymerisation ou copolymerisation radicalaire controlee de l'ethylene sous haute pression en presence d'un amorceur-controleur |
| TWI225483B (en) | 1998-10-16 | 2004-12-21 | Ciba Sc Holding Ag | Heterocyclic alkoxyamines as regulators in controlled radical polymerization process |
| 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 |
| TW546311B (en) * | 1999-11-25 | 2003-08-11 | Ciba Sc Holding Ag | Composition and method for color improvement of nitroxyl containing polymers |
| 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 |
| BR0110854B1 (pt) * | 2000-05-19 | 2017-10-24 | Ciba Specialty Chemicals Holdings Inc | Method for reducing the polypropylene molecular weight, propylene copolymers or polypropylene mixtures, as a compound |
| TW572896B (en) * | 2000-05-26 | 2004-01-21 | Ciba Sc Holding Ag | Process for the synthesis of amine ethers from secondary amino oxides |
| 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 |
| TWI236482B (en) * | 2000-11-13 | 2005-07-21 | Ciba Sc Holding Ag | Process for the (co)polymerization of vinyl chloride in the presence of a stable free nitroxyl radical |
| 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 |
| TW557305B (en) * | 2000-12-14 | 2003-10-11 | Ciba Sc Holding Ag | N-alkoxy-4,4-dioxy-polyalkyl-piperidine compounds, their corresponding n-oxides and controlled radical polymerization therewith |
| US6849679B2 (en) | 2001-05-21 | 2005-02-01 | Ciba Specialty Chemicals Corporation | Pigment compositions with modified block copolymer dispersants |
| ATE491687T1 (de) * | 2001-06-13 | 2011-01-15 | Basf Se | 4-imin-n-alkoxy- oder oxy-polyalkyl-piperidin- verbindungen zur verwendung als polymerisationsregulatoren |
| US7868171B2 (en) * | 2001-11-12 | 2011-01-11 | Ciba Specialty Chemicals Corp. | N-alkoxy-4, 4-dioxy-polyalkyl-piperidines as radical polymerization initiators |
| TW200407307A (en) * | 2001-11-26 | 2004-05-16 | Ciba Sc Holding Ag | Process for the synthesis of amine ethers from secondary amino oxides |
| US7297819B2 (en) * | 2002-03-05 | 2007-11-20 | Ciba Specialty Chemicals Corp. | Open-chain alkoxyamines and their corresponding nitroxides for controlled low temperature radical polymerization |
| DE10212831A1 (de) * | 2002-03-22 | 2003-10-02 | Tesa Ag | Verfahren zur Herstellung copolymerer Polyacrylat-Haftklebemassen, damit erhaltene Nitroxid-modifizierte Polyacrylate und Kamm-Blockpolymere |
| CA2484148A1 (en) * | 2002-05-01 | 2003-11-13 | Ciba Specialty Chemicals Holding Inc. | Process for chain stopping of pvc polymerization |
| EP1375476A1 (en) * | 2002-06-25 | 2004-01-02 | Bayer Aktiengesellschaft | A new process for the synthesis of alkoxyamines active in controlled radical polymerization |
| EP1375457A1 (en) | 2002-06-25 | 2004-01-02 | Bayer Aktiengesellschaft | One-pot process for the preparation of functionalized alkoxyamines |
| WO2004069887A2 (en) * | 2003-02-10 | 2004-08-19 | Ciba Specialty Chemicals Holding Inc. | Comb copolymers with defined side chains and process for their manufacture |
| JP4107996B2 (ja) * | 2003-04-25 | 2008-06-25 | 大塚化学株式会社 | リビングラジカルポリマーの製造方法及びポリマー |
| JP4046678B2 (ja) * | 2003-10-15 | 2008-02-13 | 横浜ゴム株式会社 | タイヤトレッド用ゴム組成物及びそれを用いた空気入りタイヤ |
| KR20100009562A (ko) * | 2004-06-09 | 2010-01-27 | 히다치 가세고교 가부시끼가이샤 | 회로접속재료, 필름상 회로접속재, 및 회로부재의 접속 구조 |
| RU2401281C2 (ru) * | 2005-01-11 | 2010-10-10 | Циба Спешиалти Кемикэлз Холдинг Инк. | Способ постмодификации гомо- и сополимеров, полученных регулируемыми процессами свободнорадикальной полимеризации |
| JP4046734B2 (ja) | 2005-01-18 | 2008-02-13 | 横浜ゴム株式会社 | ポリマーの変性方法 |
| US20090299013A1 (en) * | 2005-04-04 | 2009-12-03 | Jochen Fink | Process for the Preparation of Star and Block-Copolymers Via Epoxy-Functionalized Alkoxyamines |
| ATE465183T1 (de) * | 2005-08-30 | 2010-05-15 | Basf Se | Aus nitroxylradikalpolymerisation gewonnene polymere |
| CN101490620B (zh) * | 2006-07-11 | 2013-02-20 | 西巴控股有限公司 | 滤色器组合物 |
| US20080087380A1 (en) * | 2006-10-13 | 2008-04-17 | Dow Global Technologies Inc. | Reactively-coupled articles and related methods |
| JP2010523519A (ja) * | 2007-04-05 | 2010-07-15 | ビーエーエスエフ ソシエタス・ヨーロピア | 選択されたコポリマーを含んでいる日焼け止め剤及びパーソナルケア組成物 |
| WO2008145595A1 (en) * | 2007-06-01 | 2008-12-04 | Basf Se | Modified printable surfaces |
| KR101574815B1 (ko) * | 2007-12-18 | 2015-12-04 | 바스프 에스이 | 바이오디젤 저온 흐름 개선제 |
| WO2009090125A1 (en) | 2008-01-17 | 2009-07-23 | Basf Se | Polymeric hair dyes |
| US9062209B2 (en) * | 2009-12-01 | 2015-06-23 | Silberline Manufacturing Company, Inc. | Polymer encapsulated aluminum particulates |
| KR101524342B1 (ko) | 2010-03-30 | 2015-07-06 | 바스프 에스이 | 말단-관능화 중합체 |
| JP5930318B2 (ja) | 2010-06-29 | 2016-06-08 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ポリマー溶融物の流動特性を向上するための方法 |
| US8815982B2 (en) | 2010-07-20 | 2014-08-26 | Silberline Manufacturing Company, Inc. | Colored system |
| US8912252B2 (en) | 2010-07-20 | 2014-12-16 | Silberline Manufacturing Company, Inc. | Film-forming pigments and coating system including the same |
| ES2476367T3 (es) | 2010-07-22 | 2014-07-14 | Basf Se | Combinación de aditivos para aplicaciones de estanqueidad |
| CA2853318A1 (en) | 2011-10-25 | 2013-05-02 | Basf Se | Use of comb or block copolymers as soil antiredeposition agents and soil release agents in laundry processes |
| US9587105B2 (en) | 2012-02-23 | 2017-03-07 | Basf Se | Fluorinated acrylate block copolymers with low dynamic surface tension |
| CN103073695B (zh) * | 2012-12-27 | 2015-03-11 | 中山大学 | 一种本征型室温自修复结晶性聚合物 |
| US9790452B2 (en) | 2013-03-27 | 2017-10-17 | Basf Se | Block copolymers as soil release agents in laundry processes |
| CN105358528B (zh) | 2013-07-08 | 2021-07-20 | 巴斯夫欧洲公司 | 新型光稳定剂 |
| KR101595084B1 (ko) * | 2015-09-23 | 2016-02-29 | 주식회사 엘림산업 | 피혁용 버핑머신 |
| KR101595087B1 (ko) * | 2015-09-23 | 2016-02-18 | 주식회사 엘림산업 | 피혁용 버핑머신 구동롤러 |
| KR101635582B1 (ko) * | 2015-10-02 | 2016-07-20 | (주)이미인 | 원단 유연화 장치 |
| CN111278934B (zh) | 2017-10-23 | 2022-04-12 | 巴斯夫欧洲公司 | 硅氧烷聚合物水乳液 |
| EP4251665B1 (en) | 2020-11-30 | 2025-01-08 | Basf Se | Process of producing polymer dispersions |
| WO2022200398A1 (en) | 2021-03-26 | 2022-09-29 | Basf Se | Polymer composition comprising polyacrylic block copolymer and aromatic based polyalkyleneoxide as dispersant |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1173290A (en) * | 1966-08-24 | 1969-12-03 | Sankyo Co | Piperidine Nitroxides and process for preparing the same |
| JPS4940557B1 (https=) * | 1969-03-06 | 1974-11-02 | ||
| US3975357A (en) | 1973-04-19 | 1976-08-17 | Sankyo Company Limited | Stabilized synthetic polymer compositions |
| GB1493996A (en) * | 1975-05-28 | 1977-12-07 | Sankyo Co | 4-siloxy derivatives of polyalkylated piperidines |
| JPS5848580B2 (ja) * | 1975-05-28 | 1983-10-29 | 三共株式会社 | ゴウセイコウブンシザイリヨウヨウアンテイザイ |
| US4141883A (en) | 1975-05-28 | 1979-02-27 | Sankyo Company, Limited | Stabilization of synthetic polymers by penta-or-hexa-substituted 4-piperidinol derivatives |
| GB1478261A (en) * | 1975-05-28 | 1977-06-29 | Ciba Geigy Ag | Derivatives of 4-oxopiperidines |
| GB1492494A (en) * | 1975-05-28 | 1977-11-23 | Sankyo Co | Derivatives of 4-aminopiperidine |
| GB1496844A (en) * | 1975-05-28 | 1978-01-05 | Ciba Geigy Ag | Stabilization of polymers |
| 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 |
| DE3486145T2 (de) * | 1983-07-11 | 1993-09-23 | Commw Scient Ind Res Org | Verfahren zur polymerisation und nach diesem verfahren hergestellte polymere. |
| EP0155912A3 (de) * | 1984-03-20 | 1986-06-04 | Ciba-Geigy Ag | Strahlenstabilisierte polymere Zusammensetzungen |
| US5185448A (en) | 1991-05-07 | 1993-02-09 | Ciba-Geigy Corporation | Substituted 1-oxy-4-acyloxypiperidine and 1-oxy-4-acylaminopiperidine stabilizers |
| TW270131B (https=) * | 1993-07-13 | 1996-02-11 | Ciba Geigy | |
| EP0638617A1 (de) | 1993-08-13 | 1995-02-15 | Ciba-Geigy Ag | Pigmentsalze |
| US5608023A (en) | 1995-03-30 | 1997-03-04 | Xerox Corporation | Rate enhanced polymerization processes |
| TW358820B (en) | 1995-04-11 | 1999-05-21 | Ciba Sc Holding Ag | Synergistic stabilizer mixture |
| EP0792911A3 (en) | 1996-02-27 | 1998-01-14 | Fmc Corporation | Flame resistant polyolefin compositions |
| HU220138B (hu) | 1996-03-29 | 2001-11-28 | The Dow Chemical Co. | Szabadgyökös tömbpolimerizálási eljárás kaucsukkal módosított polimerek vinil-aromás monomerekből való előállítására |
| TW467931B (en) | 1996-08-22 | 2001-12-11 | Ciba Sc Holding Ag | Stabilizer mixtures |
| AU4773997A (en) * | 1996-09-25 | 1998-04-17 | Akzo Nobel N.V. | No-compounds for pseudo-living radical polymerization |
| EP0951485B1 (en) | 1997-01-10 | 2003-04-02 | E.I. Du Pont De Nemours And Company | Method of controlling polymer molecular weight and structure |
| US6281311B1 (en) | 1997-03-31 | 2001-08-28 | Pmd Holdings Corp. | Controlled free radical polymerization process |
| JP2001510208A (ja) * | 1997-07-15 | 2001-07-31 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | ニトロソ化合物又はニトロン化合物から誘導されたアルコキシアミン化合物を含む重合可能な組成物 |
| SG74700A1 (en) | 1998-02-25 | 2000-08-22 | Ciba Sc Holding Ag | Preparation of sterically hindered amine ethers |
| TW495515B (en) * | 1998-03-09 | 2002-07-21 | Ciba Sc Holding Ag | 1-alkoxy-polyalkyl-piperidine derivatives, a polymerizable composition containing the same and a process for polymerization |
| SG82601A1 (en) * | 1998-03-09 | 2001-08-21 | Ciba Sc Holding Ag | 1-alkoxy-polyalkyl-piperidine derivatives and their use as polymerization regulators |
| EP1115765B1 (en) * | 1998-09-03 | 2009-06-24 | Ciba Holding Inc. | Grafting of ethylenically unsaturated monomers onto polymers |
| 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
- 1999-03-02 SG SG9901047A patent/SG82601A1/en unknown
- 1999-03-02 CH CH00379/99A patent/CH693416A5/de not_active IP Right Cessation
- 1999-03-04 US US09/262,804 patent/US6353107B1/en not_active Expired - Lifetime
- 1999-03-04 BE BE9900152A patent/BE1012399A3/fr not_active IP Right Cessation
- 1999-03-05 IT IT1999MI000453A patent/IT1309590B1/it active
- 1999-03-05 DE DE1999109767 patent/DE19909767B4/de not_active Expired - Lifetime
- 1999-03-05 CZ CZ99789A patent/CZ78999A3/cs unknown
- 1999-03-05 CA CA002264460A patent/CA2264460A1/en not_active Abandoned
- 1999-03-08 AT AT0038799A patent/AT408655B/de not_active IP Right Cessation
- 1999-03-08 JP JP06019899A patent/JP4651137B2/ja not_active Expired - Lifetime
- 1999-03-08 AU AU18636/99A patent/AU754927B2/en not_active Ceased
- 1999-03-08 GB GB9905152A patent/GB2335190B/en not_active Expired - Lifetime
- 1999-03-08 FR FR9902814A patent/FR2777892B1/fr not_active Expired - Lifetime
- 1999-03-08 CN CNB991020987A patent/CN1171871C/zh not_active Expired - Lifetime
- 1999-03-08 ES ES009900470A patent/ES2155014B1/es not_active Expired - Fee Related
- 1999-03-09 KR KR1019990007738A patent/KR100581654B1/ko not_active Expired - Lifetime
- 1999-03-09 BR BRPI9900977-3B1A patent/BR9900977B1/pt active IP Right Grant
- 1999-03-09 NL NL1011493A patent/NL1011493C2/nl not_active IP Right Cessation
-
2001
- 2001-12-11 US US10/013,884 patent/US6683142B2/en not_active Expired - Lifetime
-
2003
- 2003-04-24 US US10/422,497 patent/US6927295B2/en not_active Expired - Lifetime
-
2005
- 2005-01-14 US US11/035,915 patent/US7402639B2/en not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2264460A1 (en) | 1-alkoxy-polyalkyl-piperidine derivatives and their use as polymerization regulators | |
| TW495515B (en) | 1-alkoxy-polyalkyl-piperidine derivatives, a polymerizable composition containing the same and a process for polymerization | |
| US6624306B2 (en) | 2,2,6,6 diethyl-dimethyl-1-alkoxy-piperidine compounds and their corresponding 1-oxides | |
| AU759817B2 (en) | Open chain alkoxyamine compounds and their use as polymerization regulators | |
| EP1397349B1 (en) | 4-imino-n-alkoxy or oxy-polyalkyl-piperidine compounds and their use as polymerization regulators | |
| EP1343827A1 (en) | N-alkoxy-4,4-dioxy-polyalkyl-piperidine compounds, their corresponding n-oxides and controlled radical polymerization therewith | |
| US20030212224A1 (en) | Composition and process for controlled radical polymerization using multifunctional initiator/regulator compounds | |
| EP1320554B1 (en) | Composition and process for enhancing controlled free radical polymerization |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |