CN100343285C - 在受控的自由基聚合方法中作为调节剂的杂环烷氧基胺 - Google Patents
在受控的自由基聚合方法中作为调节剂的杂环烷氧基胺 Download PDFInfo
- Publication number
- CN100343285C CN100343285C CNB991213904A CN99121390A CN100343285C CN 100343285 C CN100343285 C CN 100343285C CN B991213904 A CNB991213904 A CN B991213904A CN 99121390 A CN99121390 A CN 99121390A CN 100343285 C CN100343285 C CN 100343285C
- Authority
- CN
- China
- Prior art keywords
- alkyl
- diethyl
- group
- butyl
- tert
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- -1 Heterocyclic alkoxyl amine Chemical class 0.000 title claims abstract description 130
- 238000000034 method Methods 0.000 title claims abstract description 33
- 238000010526 radical polymerization reaction Methods 0.000 title claims description 13
- 239000000178 monomer Substances 0.000 claims abstract description 189
- 150000003254 radicals Chemical class 0.000 claims abstract description 144
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 126
- 239000000203 mixture Substances 0.000 claims abstract description 125
- 239000003999 initiator Substances 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 400
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 123
- 229910052739 hydrogen Inorganic materials 0.000 claims description 82
- 239000001257 hydrogen Substances 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- 150000002431 hydrogen Chemical group 0.000 claims description 49
- 229910052799 carbon Inorganic materials 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 229920000642 polymer Polymers 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 17
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 16
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 14
- 229920001400 block copolymer Polymers 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 238000003776 cleavage reaction Methods 0.000 claims description 7
- 230000007017 scission Effects 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- SKUZMLMCANXMFF-UHFFFAOYSA-N 2-[2,2-diethyl-6,6-dimethyl-3-oxo-4-(2,4,4-trimethylpentan-2-yl)piperazin-1-yl]oxy-2-methylpropanenitrile Chemical compound CCC1(CC)N(OC(C)(C)C#N)C(C)(C)CN(C(C)(C)CC(C)(C)C)C1=O SKUZMLMCANXMFF-UHFFFAOYSA-N 0.000 claims description 6
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 6
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- MLXQULZNIANQDT-UHFFFAOYSA-N 1-tert-butyl-3,3-diethyl-5,5-dimethyl-4-phenylmethoxypiperazin-2-one Chemical compound CC1(C)CN(C(C)(C)C)C(=O)C(CC)(CC)N1OCC1=CC=CC=C1 MLXQULZNIANQDT-UHFFFAOYSA-N 0.000 claims description 5
- GUAWSHSZRSOUMW-UHFFFAOYSA-N 1-tert-butyl-3,5,5-triethyl-3-methyl-4-phenylmethoxypiperazin-2-one Chemical compound CCC1(CC)CN(C(C)(C)C)C(=O)C(C)(CC)N1OCC1=CC=CC=C1 GUAWSHSZRSOUMW-UHFFFAOYSA-N 0.000 claims description 5
- UZBHMLIATWYOHI-UHFFFAOYSA-N 2-(2,2-dibutyl-4-tert-butyl-6,6-dimethyl-3-oxopiperazin-1-yl)oxy-2-methylpropanenitrile Chemical compound CCCCC1(CCCC)N(OC(C)(C)C#N)C(C)(C)CN(C(C)(C)C)C1=O UZBHMLIATWYOHI-UHFFFAOYSA-N 0.000 claims description 5
- AOYQRPLJAGLQQK-UHFFFAOYSA-N 2-(4-tert-butyl-2,2,6,6-tetraethyl-3-oxopiperazin-1-yl)oxy-2-methylpropanenitrile Chemical compound CCC1(CC)CN(C(C)(C)C)C(=O)C(CC)(CC)N1OC(C)(C)C#N AOYQRPLJAGLQQK-UHFFFAOYSA-N 0.000 claims description 5
- LYDWSNZBYCAGPK-UHFFFAOYSA-N 2-(4-tert-butyl-2,6,6-triethyl-2-methyl-3-oxopiperazin-1-yl)oxy-2-methylpropanenitrile Chemical compound CCC1(C)N(OC(C)(C)C#N)C(CC)(CC)CN(C(C)(C)C)C1=O LYDWSNZBYCAGPK-UHFFFAOYSA-N 0.000 claims description 5
- HWDPFCCKBAFQRC-UHFFFAOYSA-N 2-(4-tert-butyl-6,6-diethyl-2,2-dimethyl-3-oxopiperazin-1-yl)oxy-2-methylpropanenitrile Chemical compound CCC1(CC)CN(C(C)(C)C)C(=O)C(C)(C)N1OC(C)(C)C#N HWDPFCCKBAFQRC-UHFFFAOYSA-N 0.000 claims description 5
- SHEIKGMYXDSXQG-UHFFFAOYSA-N 2-(4-tert-butyl-6,6-dimethyl-3-oxo-2,2-dipropylpiperazin-1-yl)oxy-2-methylpropanenitrile Chemical compound CCCC1(CCC)N(OC(C)(C)C#N)C(C)(C)CN(C(C)(C)C)C1=O SHEIKGMYXDSXQG-UHFFFAOYSA-N 0.000 claims description 5
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 5
- RQSJAQMWOGLLAU-UHFFFAOYSA-N 4-benzyl-2,7-diethyl-2,3,7-trimethyl-1-phenylmethoxy-1,4-diazepan-5-one Chemical compound CC1C(C)(CC)N(OCC=2C=CC=CC=2)C(CC)(C)CC(=O)N1CC1=CC=CC=C1 RQSJAQMWOGLLAU-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- AAQFPIOHPXUGNM-UHFFFAOYSA-N 1-tert-butyl-3,3,5,5-tetraethyl-4-phenylmethoxypiperazin-2-one Chemical compound CCC1(CC)CN(C(C)(C)C)C(=O)C(CC)(CC)N1OCC1=CC=CC=C1 AAQFPIOHPXUGNM-UHFFFAOYSA-N 0.000 claims description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 229920005604 random copolymer Polymers 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 230000000977 initiatory effect Effects 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 230000005670 electromagnetic radiation Effects 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 claims description 2
- 238000000527 sonication Methods 0.000 claims description 2
- 150000003440 styrenes Chemical class 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 2
- 125000005250 alkyl acrylate group Chemical group 0.000 claims 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 239000002243 precursor Substances 0.000 abstract description 8
- 150000001412 amines Chemical class 0.000 abstract description 7
- 125000005262 alkoxyamine group Chemical group 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 142
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 138
- 239000000243 solution Substances 0.000 description 102
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 92
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 78
- 238000005227 gel permeation chromatography Methods 0.000 description 73
- 229910052786 argon Inorganic materials 0.000 description 71
- 239000007788 liquid Substances 0.000 description 70
- 238000004364 calculation method Methods 0.000 description 59
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 54
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
- 238000002844 melting Methods 0.000 description 50
- 230000008018 melting Effects 0.000 description 50
- 238000005160 1H NMR spectroscopy Methods 0.000 description 46
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 34
- 239000012230 colorless oil Substances 0.000 description 34
- 238000000921 elemental analysis Methods 0.000 description 32
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 32
- 239000003921 oil Substances 0.000 description 30
- 238000004458 analytical method Methods 0.000 description 28
- 238000001704 evaporation Methods 0.000 description 28
- 230000008020 evaporation Effects 0.000 description 27
- 239000013078 crystal Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000009826 distribution Methods 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 17
- 239000002904 solvent Substances 0.000 description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 11
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- NYIPOHVLRWJXJY-UHFFFAOYSA-N 3-ethyl-3,5,5-trimethyl-1-propan-2-ylpiperazin-2-one Chemical compound CCC1(C)NC(C)(C)CN(C(C)C)C1=O NYIPOHVLRWJXJY-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- BIQOVFVAJAEPIR-UHFFFAOYSA-N 2-(2-ethyl-2,6,6-trimethyl-3-oxo-4-propan-2-ylpiperazin-1-yl)oxy-2-methylpropanenitrile Chemical compound CCC1(C)N(OC(C)(C)C#N)C(C)(C)CN(C(C)C)C1=O BIQOVFVAJAEPIR-UHFFFAOYSA-N 0.000 description 8
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- YSLQIELHSIUJTR-UHFFFAOYSA-N 3,3-diethyl-5,5-dimethylmorpholin-2-one Chemical compound CCC1(CC)NC(C)(C)COC1=O YSLQIELHSIUJTR-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- KKWUZQSPIBAUDN-UHFFFAOYSA-N 1-tert-butyl-3,3,5-triethyl-5-methyl-4-(1-phenylethoxy)piperazin-2-one Chemical compound CCC1(C)CN(C(C)(C)C)C(=O)C(CC)(CC)N1OC(C)C1=CC=CC=C1 KKWUZQSPIBAUDN-UHFFFAOYSA-N 0.000 description 6
- VFIXFSTVCVVOML-UHFFFAOYSA-N 1-tert-butyl-3,3-diethyl-5,5-dimethyl-4-(1-phenylethoxy)piperazin-2-one Chemical compound CC1(C)CN(C(C)(C)C)C(=O)C(CC)(CC)N1OC(C)C1=CC=CC=C1 VFIXFSTVCVVOML-UHFFFAOYSA-N 0.000 description 6
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- JBNBGZUYAWNMDG-UHFFFAOYSA-N 1-tert-butyl-3-ethyl-3,5,5-trimethyl-4-(1-phenylethoxy)piperazin-2-one Chemical compound CC1(C)CN(C(C)(C)C)C(=O)C(CC)(C)N1OC(C)C1=CC=CC=C1 JBNBGZUYAWNMDG-UHFFFAOYSA-N 0.000 description 5
- 229920000578 graft copolymer Polymers 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- CGWSBVNBUPEXNY-UHFFFAOYSA-N (3,5,5-triethyl-6-oxomorpholin-3-yl)methyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCC1(CC)COC(=O)C(CC)(CC)N1 CGWSBVNBUPEXNY-UHFFFAOYSA-N 0.000 description 4
- BTSDTBBXGVOIDN-UHFFFAOYSA-N (5,5-diethyl-3-methyl-6-oxomorpholin-3-yl)methyl 2,2-dimethylpropanoate Chemical compound CCC1(CC)NC(C)(COC(=O)C(C)(C)C)COC1=O BTSDTBBXGVOIDN-UHFFFAOYSA-N 0.000 description 4
- XJYJNEVOBUSPSR-UHFFFAOYSA-N 1-benzyl-3,3-diethyl-5,5-dimethylpiperazin-2-one Chemical compound O=C1C(CC)(CC)NC(C)(C)CN1CC1=CC=CC=C1 XJYJNEVOBUSPSR-UHFFFAOYSA-N 0.000 description 4
- XCDAPYJGQJAAPG-UHFFFAOYSA-N 1-tert-butyl-3,3-diethyl-5,5-dimethylpiperazin-2-one Chemical compound CCC1(CC)NC(C)(C)CN(C(C)(C)C)C1=O XCDAPYJGQJAAPG-UHFFFAOYSA-N 0.000 description 4
- IONRRIGXSWYKKC-UHFFFAOYSA-N 1-tert-butyl-3,5,5-triethyl-3-methyl-4-(1-phenylethoxy)piperazin-2-one Chemical compound CCC1(CC)CN(C(C)(C)C)C(=O)C(C)(CC)N1OC(C)C1=CC=CC=C1 IONRRIGXSWYKKC-UHFFFAOYSA-N 0.000 description 4
- DEMLMDLMVWXHRC-UHFFFAOYSA-N 1-tert-butyl-3,5,5-trimethyl-3-(2-methylpropyl)-4-(1-phenylethoxy)piperazin-2-one Chemical compound CC1(C)CN(C(C)(C)C)C(=O)C(CC(C)C)(C)N1OC(C)C1=CC=CC=C1 DEMLMDLMVWXHRC-UHFFFAOYSA-N 0.000 description 4
- JZIQRHNKFBJEER-UHFFFAOYSA-N 1-tert-butyl-3,5-diethyl-3,5-dimethyl-4-(1-phenylethoxy)piperazin-2-one Chemical compound CCC1(C)CN(C(C)(C)C)C(=O)C(C)(CC)N1OC(C)C1=CC=CC=C1 JZIQRHNKFBJEER-UHFFFAOYSA-N 0.000 description 4
- ARTINEXELSVQFU-UHFFFAOYSA-N 2,2,5,5-tetraethylimidazolidin-4-one Chemical compound CCC1(CC)NC(=O)C(CC)(CC)N1 ARTINEXELSVQFU-UHFFFAOYSA-N 0.000 description 4
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 4
- ITGOMIKKVVXDLE-UHFFFAOYSA-N 2,7-diethyl-2,3,4,7-tetramethyl-1-(1-phenylethoxy)-1,4-diazepan-5-one Chemical compound CCC1(C)CC(=O)N(C)C(C)C(C)(CC)N1OC(C)C1=CC=CC=C1 ITGOMIKKVVXDLE-UHFFFAOYSA-N 0.000 description 4
- YMYLSGJIPSOSTE-UHFFFAOYSA-N 2-(2,2-diethyl-6,6-dimethyl-3-oxo-4-propan-2-ylpiperazin-1-yl)oxy-2-methylpropanenitrile Chemical compound CCC1(CC)N(OC(C)(C)C#N)C(C)(C)CN(C(C)C)C1=O YMYLSGJIPSOSTE-UHFFFAOYSA-N 0.000 description 4
- JNOKYCCKHUYBQZ-UHFFFAOYSA-N 2-(3,3-diethyl-5,5-dimethyl-2-oxomorpholin-4-yl)oxy-2-methylpropanenitrile Chemical compound CCC1(CC)N(OC(C)(C)C#N)C(C)(C)COC1=O JNOKYCCKHUYBQZ-UHFFFAOYSA-N 0.000 description 4
- ZLSULMZGWDODMA-UHFFFAOYSA-N 2-(4-tert-butyl-2,2-diethyl-6,6-dimethyl-3-oxopiperazin-1-yl)oxy-2-methylpropanenitrile Chemical compound CCC1(CC)N(OC(C)(C)C#N)C(C)(C)CN(C(C)(C)C)C1=O ZLSULMZGWDODMA-UHFFFAOYSA-N 0.000 description 4
- YOIPYKKWCRTZDK-UHFFFAOYSA-N 2-(6,6-diethyl-2,2,3,3-tetramethyl-5-oxopiperazin-1-yl)oxy-2-methylpropanenitrile Chemical compound CCC1(CC)N(OC(C)(C)C#N)C(C)(C)C(C)(C)NC1=O YOIPYKKWCRTZDK-UHFFFAOYSA-N 0.000 description 4
- RMRHAXNPDCHLRX-UHFFFAOYSA-N 2-[2,2-diethyl-4-(1-hydroxy-2-methylpropan-2-yl)-6,6-dimethyl-3-oxopiperazin-1-yl]oxy-2-methylpropanenitrile Chemical compound CCC1(CC)N(OC(C)(C)C#N)C(C)(C)CN(C(C)(C)CO)C1=O RMRHAXNPDCHLRX-UHFFFAOYSA-N 0.000 description 4
- SPXJPAPOMQYVPI-UHFFFAOYSA-N 2-[2,2-diethyl-4-(2-hydroxyethyl)-6,6-dimethyl-3-oxopiperazin-1-yl]oxy-2-methylpropanenitrile Chemical compound CCC1(CC)N(OC(C)(C)C#N)C(C)(C)CN(CCO)C1=O SPXJPAPOMQYVPI-UHFFFAOYSA-N 0.000 description 4
- NCQJRXVOOIVKQN-UHFFFAOYSA-N 3,3,5,5-tetraethylmorpholin-2-one Chemical compound CCC1(CC)COC(=O)C(CC)(CC)N1 NCQJRXVOOIVKQN-UHFFFAOYSA-N 0.000 description 4
- ORQVHQKOHXDDCZ-UHFFFAOYSA-N 3,3,5-triethyl-5-(hydroxymethyl)morpholin-2-one Chemical compound CCC1(CO)COC(=O)C(CC)(CC)N1 ORQVHQKOHXDDCZ-UHFFFAOYSA-N 0.000 description 4
- YXKOHXRRQKDSCO-UHFFFAOYSA-N 3,3-diethyl-1-(2-hydroxyethyl)-5,5-dimethylpiperazin-2-one Chemical compound CCC1(CC)NC(C)(C)CN(CCO)C1=O YXKOHXRRQKDSCO-UHFFFAOYSA-N 0.000 description 4
- YWZJDYQIWVIBST-UHFFFAOYSA-N 3,3-diethyl-5,5,6,6-tetramethylpiperazin-2-one Chemical compound CCC1(CC)NC(C)(C)C(C)(C)NC1=O YWZJDYQIWVIBST-UHFFFAOYSA-N 0.000 description 4
- LIZJQJSMXQKLMG-UHFFFAOYSA-N 3,3-diethyl-5,5-dimethyl-1-propan-2-ylpiperazin-2-one Chemical compound CCC1(CC)NC(C)(C)CN(C(C)C)C1=O LIZJQJSMXQKLMG-UHFFFAOYSA-N 0.000 description 4
- WDLYLMJXDLUTSG-UHFFFAOYSA-N 3,3-diethyl-5,5-dimethyl-4-(1-phenylethoxy)-1-propan-2-ylpiperazin-2-one Chemical compound CC1(C)CN(C(C)C)C(=O)C(CC)(CC)N1OC(C)C1=CC=CC=C1 WDLYLMJXDLUTSG-UHFFFAOYSA-N 0.000 description 4
- JUTAUOIJEXFUAA-UHFFFAOYSA-N 3,3-diethyl-5-(hydroxymethyl)-5-methylmorpholin-2-one Chemical compound CCC1(CC)NC(C)(CO)COC1=O JUTAUOIJEXFUAA-UHFFFAOYSA-N 0.000 description 4
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- IRGZHLWDILRYSA-UHFFFAOYSA-N [3,5,5-triethyl-6-oxo-4-(1-phenylethoxy)morpholin-3-yl]methyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCC1(CC)COC(=O)C(CC)(CC)N1OC(C)C1=CC=CC=C1 IRGZHLWDILRYSA-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 244000309464 bull Species 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- RTTPXVFZNHJZBN-UHFFFAOYSA-N 1-n-tert-butyl-2-methylbutane-1,2-diamine Chemical compound CCC(C)(N)CNC(C)(C)C RTTPXVFZNHJZBN-UHFFFAOYSA-N 0.000 description 3
- HJVXTKQNOPXNJW-UHFFFAOYSA-N 1-tert-butyl-3,3,5,5-tetraethylpiperazin-2-one Chemical compound CCC1(CC)CN(C(C)(C)C)C(=O)C(CC)(CC)N1 HJVXTKQNOPXNJW-UHFFFAOYSA-N 0.000 description 3
- OPZBWPPKTGWDLN-UHFFFAOYSA-N 1-tert-butyl-3,3,5-triethyl-5-methylpiperazin-2-one Chemical compound CCC1(C)CN(C(C)(C)C)C(=O)C(CC)(CC)N1 OPZBWPPKTGWDLN-UHFFFAOYSA-N 0.000 description 3
- OINMIGAEHQMAPX-UHFFFAOYSA-N 1-tert-butyl-3,5,5-triethyl-3-methylpiperazin-2-one Chemical compound CCC1(CC)CN(C(C)(C)C)C(=O)C(C)(CC)N1 OINMIGAEHQMAPX-UHFFFAOYSA-N 0.000 description 3
- DWVFCHJCAHCAPS-UHFFFAOYSA-N 1-tert-butyl-3,5,5-trimethyl-3-(2-methylpropyl)piperazin-2-one Chemical compound CC(C)CC1(C)NC(C)(C)CN(C(C)(C)C)C1=O DWVFCHJCAHCAPS-UHFFFAOYSA-N 0.000 description 3
- XUYWAXVJTVZUGK-UHFFFAOYSA-N 1-tert-butyl-3,5-diethyl-3,5-dimethylpiperazin-2-one Chemical compound CCC1(C)CN(C(C)(C)C)C(=O)C(C)(CC)N1 XUYWAXVJTVZUGK-UHFFFAOYSA-N 0.000 description 3
- FONNYDACTANTGT-UHFFFAOYSA-N 1-tert-butyl-3-ethyl-3,5,5-trimethylpiperazin-2-one Chemical compound CCC1(C)NC(C)(C)CN(C(C)(C)C)C1=O FONNYDACTANTGT-UHFFFAOYSA-N 0.000 description 3
- BAMPADUCVOQPMN-UHFFFAOYSA-N 1-tert-butyl-5,5-diethyl-3,3-dimethylpiperazin-2-one Chemical compound CCC1(CC)CN(C(C)(C)C)C(=O)C(C)(C)N1 BAMPADUCVOQPMN-UHFFFAOYSA-N 0.000 description 3
- RZYJMZGSUWYXJW-UHFFFAOYSA-N 1-tert-butyl-5,5-diethyl-3,3-dipropylpiperazin-2-one Chemical compound CCCC1(CCC)NC(CC)(CC)CN(C(C)(C)C)C1=O RZYJMZGSUWYXJW-UHFFFAOYSA-N 0.000 description 3
- HHVOXQQGUFEJDM-UHFFFAOYSA-N 1-tert-butyl-5,5-dimethyl-3,3-dipropylpiperazin-2-one Chemical compound CCCC1(CCC)NC(C)(C)CN(C(C)(C)C)C1=O HHVOXQQGUFEJDM-UHFFFAOYSA-N 0.000 description 3
- OUXZUYYNBACOLC-UHFFFAOYSA-N 2-(2,5-diethyl-2,5-dimethyl-4-oxoimidazolidin-1-yl)oxy-2-methylpropanenitrile Chemical compound CCC1(C)NC(=O)C(C)(CC)N1OC(C)(C)C#N OUXZUYYNBACOLC-UHFFFAOYSA-N 0.000 description 3
- HPOKJLFNDLWVBS-UHFFFAOYSA-N 2-(3-ethyl-3,5,5-trimethyl-2-oxomorpholin-4-yl)oxy-2-methylpropanenitrile Chemical compound CCC1(C)N(OC(C)(C)C#N)C(C)(C)COC1=O HPOKJLFNDLWVBS-UHFFFAOYSA-N 0.000 description 3
- KFFPIBIUMPOVIS-UHFFFAOYSA-N 2-methyl-2-(2,2,5,5-tetraethyl-4-oxoimidazolidin-1-yl)oxypropanenitrile Chemical compound CCC1(CC)NC(=O)C(CC)(CC)N1OC(C)(C)C#N KFFPIBIUMPOVIS-UHFFFAOYSA-N 0.000 description 3
- FPCBSDQYBHPPFH-UHFFFAOYSA-N 3,3-dibutyl-1-tert-butyl-5,5-dimethylpiperazin-2-one Chemical compound CCCCC1(CCCC)NC(C)(C)CN(C(C)(C)C)C1=O FPCBSDQYBHPPFH-UHFFFAOYSA-N 0.000 description 3
- PGNDDDQJWNFHIZ-UHFFFAOYSA-N 3,3-diethyl-1,5,5-trimethylpiperazin-2-one Chemical compound CCC1(CC)NC(C)(C)CN(C)C1=O PGNDDDQJWNFHIZ-UHFFFAOYSA-N 0.000 description 3
- NOBMHBRBUYKKAF-UHFFFAOYSA-N 3,3-diethyl-1-(1-hydroxy-2-methylpropan-2-yl)-5,5-dimethylpiperazin-2-one Chemical compound CCC1(CC)NC(C)(C)CN(C(C)(C)CO)C1=O NOBMHBRBUYKKAF-UHFFFAOYSA-N 0.000 description 3
- XQYMZVHFHTVFLN-UHFFFAOYSA-N 3,3-diethyl-5,5-dimethyl-1-(2,4,4-trimethylpentan-2-yl)piperazin-2-one Chemical compound CCC1(CC)NC(C)(C)CN(C(C)(C)CC(C)(C)C)C1=O XQYMZVHFHTVFLN-UHFFFAOYSA-N 0.000 description 3
- ARDLGYZNRALACF-UHFFFAOYSA-N 3,3-diethyl-5,5-dimethyl-1-phenylpiperazin-2-one Chemical compound O=C1C(CC)(CC)NC(C)(C)CN1C1=CC=CC=C1 ARDLGYZNRALACF-UHFFFAOYSA-N 0.000 description 3
- CUZNNTLPNGPRQV-UHFFFAOYSA-N 3-ethyl-3,5,5-trimethyl-4-(1-phenylethoxy)-1-propan-2-ylpiperazin-2-one Chemical compound CC1(C)CN(C(C)C)C(=O)C(CC)(C)N1OC(C)C1=CC=CC=C1 CUZNNTLPNGPRQV-UHFFFAOYSA-N 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZPBIZXZRZLYZOU-UHFFFAOYSA-N [4-(2-cyanopropan-2-yloxy)-3,5,5-trimethyl-6-oxomorpholin-3-yl]methyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCC1(C)COC(=O)C(C)(C)N1OC(C)(C)C#N ZPBIZXZRZLYZOU-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical group BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000006184 cosolvent Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000005297 pyrex Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- BZUZUWIQVUXQEG-UHFFFAOYSA-N (3,5,5-trimethyl-6-oxomorpholin-3-yl)methyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCC1(C)COC(=O)C(C)(C)N1 BZUZUWIQVUXQEG-UHFFFAOYSA-N 0.000 description 2
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-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
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- MPIDCLUTYWQINY-UHFFFAOYSA-N 4-butyl-2,2,5,7,7-pentamethyl-1h-1,4-diazepin-3-one Chemical compound CCCCN1C(C)=CC(C)(C)NC(C)(C)C1=O MPIDCLUTYWQINY-UHFFFAOYSA-N 0.000 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 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- BVVNMQQFLWWRFT-UHFFFAOYSA-N N(1)-isopropyl-2-methylpropan-1,2-diamine Chemical compound CC(C)NCC(C)(C)N BVVNMQQFLWWRFT-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- 238000007323 disproportionation reaction Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- 229920006030 multiblock copolymer Polymers 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical class O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 description 2
- JTHRRMFZHSDGNJ-UHFFFAOYSA-N piperazine-2,3-dione Chemical class O=C1NCCNC1=O JTHRRMFZHSDGNJ-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 229940090181 propyl acetate Drugs 0.000 description 2
- 238000001542 size-exclusion chromatography Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 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
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-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
- BRLVXFONMZRJCD-UHFFFAOYSA-N (3-azaniumyl-2,3-dimethylbutan-2-yl)azanium;dichloride Chemical compound Cl.Cl.CC(C)(N)C(C)(C)N BRLVXFONMZRJCD-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
- 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
- FGDZIAMRHXEPLG-UHFFFAOYSA-N 1,2,2,3-tetramethylpyrrolidine Chemical compound CC1CCN(C)C1(C)C FGDZIAMRHXEPLG-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 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
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 1
- ZRIUABLAYPQZGA-UHFFFAOYSA-N 1-n-benzyl-2-methylpropane-1,2-diamine Chemical compound CC(C)(N)CNCC1=CC=CC=C1 ZRIUABLAYPQZGA-UHFFFAOYSA-N 0.000 description 1
- RLXGVAKVMJUGIE-UHFFFAOYSA-N 1-tert-butyl-3,3-diethyl-4-hydroxy-5,5-dimethylpiperazin-2-one Chemical compound CCC1(CC)N(O)C(C)(C)CN(C(C)(C)C)C1=O RLXGVAKVMJUGIE-UHFFFAOYSA-N 0.000 description 1
- GOAHRBQLKIZLKG-UHFFFAOYSA-N 1-tert-butylperoxybutane Chemical compound CCCCOOC(C)(C)C GOAHRBQLKIZLKG-UHFFFAOYSA-N 0.000 description 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-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
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- OEDKOOAJXTXCQZ-UHFFFAOYSA-N 2-[(2-amino-2-methylpropyl)amino]ethanol Chemical compound CC(C)(N)CNCCO OEDKOOAJXTXCQZ-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
- RJICLMDXEDUMAK-UHFFFAOYSA-N 2-amino-2-ethylbutan-1-ol Chemical compound CCC(N)(CC)CO RJICLMDXEDUMAK-UHFFFAOYSA-N 0.000 description 1
- IOAOAKDONABGPZ-UHFFFAOYSA-N 2-amino-2-ethylpropane-1,3-diol Chemical compound CCC(N)(CO)CO IOAOAKDONABGPZ-UHFFFAOYSA-N 0.000 description 1
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 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
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-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
- JTQWEPYYUBACDU-UHFFFAOYSA-N 2-methyl-2-propylperoxypropane Chemical compound CCCOOC(C)(C)C JTQWEPYYUBACDU-UHFFFAOYSA-N 0.000 description 1
- RAWISQFSQWIXCW-UHFFFAOYSA-N 2-methylbutan-2-yl 2,2-dimethyloctaneperoxoate Chemical compound CCCCCCC(C)(C)C(=O)OOC(C)(C)CC RAWISQFSQWIXCW-UHFFFAOYSA-N 0.000 description 1
- RFSCGDQQLKVJEJ-UHFFFAOYSA-N 2-methylbutan-2-yl benzenecarboperoxoate Chemical compound CCC(C)(C)OOC(=O)C1=CC=CC=C1 RFSCGDQQLKVJEJ-UHFFFAOYSA-N 0.000 description 1
- RCEJCSULJQNRQQ-UHFFFAOYSA-N 2-methylbutanenitrile Chemical compound CCC(C)C#N RCEJCSULJQNRQQ-UHFFFAOYSA-N 0.000 description 1
- PDYXVZHOLWKKTM-UHFFFAOYSA-N 2-methylpropanamide;dihydrate Chemical compound O.O.CC(C)C(N)=O PDYXVZHOLWKKTM-UHFFFAOYSA-N 0.000 description 1
- NDAJNMAAXXIADY-UHFFFAOYSA-N 2-methylpropanimidamide Chemical compound CC(C)C(N)=N NDAJNMAAXXIADY-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- SUGZATOHBPXTDV-UHFFFAOYSA-N 2-nitrobutane Chemical compound CCC(C)[N+]([O-])=O SUGZATOHBPXTDV-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
- 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
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- KGKBDJTUKBJFEU-UHFFFAOYSA-N 3-ethyl-3,5,5-trimethylmorpholin-2-one Chemical compound CCC1(C)NC(C)(C)COC1=O KGKBDJTUKBJFEU-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- HXKNOTGMRCTSEU-UHFFFAOYSA-N 3-n-tert-butyl-2-methylbutane-2,3-diamine Chemical compound CC(N)(C)C(C)NC(C)(C)C HXKNOTGMRCTSEU-UHFFFAOYSA-N 0.000 description 1
- RXPKOTQRDGEKFY-UHFFFAOYSA-N 3-nitropentane Chemical compound CCC(CC)[N+]([O-])=O RXPKOTQRDGEKFY-UHFFFAOYSA-N 0.000 description 1
- OXGOEZHUKDEEKS-UHFFFAOYSA-N 3-tert-butylperoxy-1,1,5-trimethylcyclohexane Chemical compound CC1CC(OOC(C)(C)C)CC(C)(C)C1 OXGOEZHUKDEEKS-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
- RTANHMOFHGSZQO-UHFFFAOYSA-N 4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)C#N RTANHMOFHGSZQO-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
- CHWVDGYLKPLBES-UHFFFAOYSA-N 5-(2-methoxyphenyl)-2-furoic acid Chemical compound COC1=CC=CC=C1C1=CC=C(C(O)=O)O1 CHWVDGYLKPLBES-UHFFFAOYSA-N 0.000 description 1
- OWYUMUPFWNDORQ-UHFFFAOYSA-N 5-(hydroxymethyl)-3,3,5-trimethylmorpholin-2-one Chemical compound CC1(C)NC(C)(CO)COC1=O OWYUMUPFWNDORQ-UHFFFAOYSA-N 0.000 description 1
- 125000003341 7 membered heterocyclic group Chemical group 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
- 238000006237 Beckmann rearrangement reaction Methods 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229910004039 HBF4 Inorganic materials 0.000 description 1
- 229910004713 HPF6 Inorganic materials 0.000 description 1
- WZELXJBMMZFDDU-UHFFFAOYSA-N Imidazol-2-one Chemical class O=C1N=CC=N1 WZELXJBMMZFDDU-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
- 238000006725 Meisenheimer rearrangement reaction Methods 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 238000010934 O-alkylation reaction Methods 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 238000006085 Schmidt reaction Methods 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000746422 Stipa Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 150000008360 acrylonitriles Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000919 ceramic Substances 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
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 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
- BSVQJWUUZCXSOL-UHFFFAOYSA-N cyclohexylsulfonyl ethaneperoxoate Chemical compound CC(=O)OOS(=O)(=O)C1CCCCC1 BSVQJWUUZCXSOL-UHFFFAOYSA-N 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([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
- 239000003599 detergent Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 229920000359 diblock copolymer Polymers 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 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
- 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
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 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
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000017525 heat dissipation Effects 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
- 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
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000012690 ionic polymerization Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 235000013847 iso-butane Nutrition 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 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
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- DUVTXUGBACWHBP-UHFFFAOYSA-N methyl 2-(1h-benzimidazol-2-ylmethoxy)benzoate Chemical compound COC(=O)C1=CC=CC=C1OCC1=NC2=CC=CC=C2N1 DUVTXUGBACWHBP-UHFFFAOYSA-N 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
- 239000011707 mineral Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical class O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BUGISVZCMXHOHO-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-2-[[1-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCC(CO)(CO)NC(=O)C(C)(C)N=NC(C)(C)C(=O)NC(CO)(CO)CO BUGISVZCMXHOHO-UHFFFAOYSA-N 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- CATWEXRJGNBIJD-UHFFFAOYSA-N n-tert-butyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NC(C)(C)C CATWEXRJGNBIJD-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- QRMPKOFEUHIBNM-UHFFFAOYSA-N p-dimethylcyclohexane Natural products CC1CCC(C)CC1 QRMPKOFEUHIBNM-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical group CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005553 polystyrene-acrylate Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- KQYLUTYUZIVHND-UHFFFAOYSA-N tert-butyl 2,2-dimethyloctaneperoxoate Chemical compound CCCCCCC(C)(C)C(=O)OOC(C)(C)C KQYLUTYUZIVHND-UHFFFAOYSA-N 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 1
- ZUSDEBDNDIJDMZ-UHFFFAOYSA-N tert-butyl 7-methyloctaneperoxoate Chemical compound CC(C)CCCCCC(=O)OOC(C)(C)C ZUSDEBDNDIJDMZ-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229920000428 triblock copolymer Polymers 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/36—One oxygen atom with hydrocarbon radicals, substituted by nitrogen atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
- C07D265/32—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings with oxygen atoms directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polymerization Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Hydrogenated Pyridines (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98811030.0 | 1998-10-16 | ||
| EP98811030 | 1998-10-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1253954A CN1253954A (zh) | 2000-05-24 |
| CN100343285C true CN100343285C (zh) | 2007-10-17 |
Family
ID=8236385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB991213904A Expired - Fee Related CN100343285C (zh) | 1998-10-16 | 1999-10-15 | 在受控的自由基聚合方法中作为调节剂的杂环烷氧基胺 |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US6479608B1 (enExample) |
| JP (1) | JP4895416B2 (enExample) |
| KR (1) | KR100597892B1 (enExample) |
| CN (1) | CN100343285C (enExample) |
| AU (1) | AU769061B2 (enExample) |
| BE (1) | BE1012727A5 (enExample) |
| BR (1) | BR9904685A (enExample) |
| CA (1) | CA2286375A1 (enExample) |
| DE (1) | DE19949352B4 (enExample) |
| DK (1) | DK199901463A (enExample) |
| ES (1) | ES2178908B1 (enExample) |
| FR (1) | FR2784684B1 (enExample) |
| GB (1) | GB2342649B (enExample) |
| IT (1) | IT1313663B1 (enExample) |
| NL (1) | NL1013259C2 (enExample) |
| SE (1) | SE522619C2 (enExample) |
| TW (1) | TWI225483B (enExample) |
Families Citing this family (81)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| WO2001023435A1 (en) * | 1999-09-30 | 2001-04-05 | Noveon Ip Holdings Corp. | Polymerization compositions and methods |
| 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 |
| US7030196B2 (en) | 2000-05-19 | 2006-04-18 | Ciba Specialty Chemicals Corporation | Process for reducing the molecular weight of polypropylene |
| DE10036801A1 (de) | 2000-07-28 | 2002-02-07 | Tesa Ag | Acrylathaftklebemassen mit enger Molekulargewichtsverteilung |
| TWI225492B (en) † | 2000-09-25 | 2004-12-21 | Ciba Sc Holding Ag | Composition and process for enhancing controlled free radical polymerization |
| TW574236B (en) * | 2000-09-25 | 2004-02-01 | Ciba Sc Holding Ag | Process for controlled radical polymerization in aqueous dispersion |
| JP4505980B2 (ja) * | 2000-11-28 | 2010-07-21 | 東レ株式会社 | アクリロニトリル系重合体の製造法 |
| US6544304B2 (en) | 2001-04-02 | 2003-04-08 | Ciba Specialty Chemicals Corporation | Candle wax stabilized with morpholinones |
| CA2443718A1 (en) * | 2001-06-13 | 2002-12-19 | Ciba Specialty Chemicals Holding Inc. | 4-imino-n-alkoxy or oxy-polyalkyl-piperidine compounds and their use as polymerization regulators |
| DE10129608A1 (de) | 2001-06-20 | 2003-05-28 | Tesa Ag | Stripfähige Systeme auf Basis von Acrylatblockcopolymeren |
| DE10133727A1 (de) * | 2001-07-11 | 2003-01-23 | Borchers Gmbh | Verwendung von Mischungen spezieller organischer Verbindungen als Hautverhinderungsmittel in lufttrocknenden Lacken |
| US20030073835A1 (en) | 2001-07-31 | 2003-04-17 | Dario Lazzari | Imidazolidinone derivatives |
| DE10149084A1 (de) | 2001-10-05 | 2003-06-18 | Tesa Ag | UV-vernetzbare Acrylathaftschmelzhaftkleber mit enger Molekulargewichtsverteilung |
| DE10149083A1 (de) | 2001-10-05 | 2003-04-17 | Tesa Ag | Acrylathaftklebemassen mit enger Molekulargewichtsverteilung |
| DE10153677A1 (de) | 2001-10-31 | 2003-05-15 | Tesa Ag | Doppelseitiges Klebeband |
| DE10156088A1 (de) | 2001-11-16 | 2003-06-05 | Tesa Ag | Orientierte Acrylatblockcopolymere |
| DE10157154A1 (de) * | 2001-11-22 | 2003-05-28 | Tesa Ag | Verfahren zur Herstellung orientierter Acrylathotmelts |
| JP2005510596A (ja) | 2001-11-24 | 2005-04-21 | テサ・アクチエンゲゼルシヤフト | 光開始剤による開始を受けるポリアクリレートの架橋 |
| DE10221093A1 (de) | 2002-05-11 | 2003-11-20 | Tesa Ag | Verwendung von Makromonomeren für die Herstellung von Acrylathaftklebemassen |
| DE10234246A1 (de) | 2002-07-27 | 2004-02-05 | Tesa Ag | Haftklebemassen mit hohem Brechungsindex auf Basis von Acrylatblockcopolymeren |
| DE10237950A1 (de) * | 2002-08-20 | 2004-03-11 | Tesa Ag | UV-initiiert thermisch vernetzte Acrylathaftklebemassen |
| DE60325380D1 (de) * | 2002-09-04 | 2009-01-29 | Ciba Holding Inc | Verfahren zur herstellung von kammförmigen und sternförmigen copolymeren mit hilfe von mit epoxidgruppen funktionalisierten nitroxylethern |
| DE10256782A1 (de) * | 2002-12-05 | 2004-08-05 | Tesa Ag | Haftklebeartikel |
| DE10259451A1 (de) * | 2002-12-19 | 2004-07-08 | Tesa Ag | Haftklebeartikel mit wenigstens einer Schicht aus einer thermisch leitfähigen Haftklebemasse und Verfahren zu seiner Herstellung |
| DE10314898A1 (de) * | 2003-01-29 | 2004-08-12 | Tesa Ag | Haftklebebänder zur Verklebung von Druckplatten und Verfahren zu deren Herstellung |
| DE10312062A1 (de) * | 2003-03-18 | 2004-09-30 | Tesa Ag | Schmelzhaftkleber mit geringem Rückschrumpf, Verfahren zu seiner Herstellung und Verwendung |
| DE10322830A1 (de) * | 2003-05-19 | 2004-12-09 | Tesa Ag | Verfahren zur kontinuierlichen Herstellung von Polymeren aus vinylischen Verbindungen durch Substanz-beziehungsweise Lösungsmittelpolymerisation |
| DE50309603D1 (de) * | 2003-05-30 | 2008-05-21 | Tesa Ag | Polyacrylathaltige haftklebemasse und -artikel sowie zugehöriges hotmelt-verarbeitungsverfahren |
| DE10357322A1 (de) | 2003-12-05 | 2005-06-30 | Tesa Ag | Zweischichtige Haftklebemasse |
| DE10357323A1 (de) | 2003-12-05 | 2005-06-30 | Tesa Ag | Haftklebemasse |
| DE10359350A1 (de) | 2003-12-16 | 2005-07-14 | Tesa Ag | Haftklebemasse |
| DE10359349A1 (de) * | 2003-12-16 | 2005-07-14 | Tesa Ag | Verfahren zur Herstellung von Acrylatschmelzhaftklebern |
| DE10359973A1 (de) | 2003-12-18 | 2005-07-21 | Tesa Ag | Haftklebemasse auf Basis von Acrylatblockcopolymeren |
| DE102004001412A1 (de) | 2004-01-09 | 2005-08-25 | Tesa Ag | Haftklebemasse auf Basis eines Acrylatpolymerblends |
| JP2005232103A (ja) * | 2004-02-20 | 2005-09-02 | Nagase & Co Ltd | 光学活性なビシナルジアミンおよびその製造方法 |
| DE102004013699A1 (de) * | 2004-03-18 | 2005-10-06 | Tesa Ag | Haftklebeband für medizinische Diagnosestreifen |
| US20100210800A1 (en) | 2004-03-24 | 2010-08-19 | Ciba Corporation | Method of preparing ethylene polymers by controlled high pressure polymerization |
| DE602005003808T2 (de) * | 2004-03-24 | 2008-12-04 | Ciba Holding Inc. | Verfahren zur herstellung von ethylenpolymeren durch kontrollierte hochdruckpolymerisation |
| DE502005007001D1 (de) | 2004-06-23 | 2009-05-14 | Tesa Ag | Medizinischer biosensor, mittels dem biologische flussigkeiten untersucht werden |
| DE102004033242A1 (de) * | 2004-07-08 | 2006-02-02 | Tesa Ag | Haftklebemasse |
| DE102004044085A1 (de) | 2004-09-09 | 2006-03-16 | Tesa Ag | Haftklebemasse mit dualem Vernetzungsmechanismus |
| US7605212B2 (en) | 2004-09-09 | 2009-10-20 | Tesa Se | Method for producing contact adhesive masses containing acrylic |
| RU2401281C2 (ru) | 2005-01-11 | 2010-10-10 | Циба Спешиалти Кемикэлз Холдинг Инк. | Способ постмодификации гомо- и сополимеров, полученных регулируемыми процессами свободнорадикальной полимеризации |
| US7410694B2 (en) | 2005-04-11 | 2008-08-12 | Tesa Aktiengesellschaft | Adhesive |
| DE102006035786A1 (de) * | 2006-07-28 | 2008-03-13 | Tesa Ag | Haftklebefolie mit hoher optischer Transparenz zur Verklebung als Splitterschutz auf Glasscheiben in Konsumgüterelektronikbauteilen |
| DE102006042816A1 (de) * | 2006-09-08 | 2008-06-26 | Tesa Ag | Hitze-aktiviert verklebbares Stanzungsflächenelement |
| CN102391601B (zh) * | 2006-09-15 | 2014-08-27 | 可乐丽股份有限公司 | 甲基丙烯酸树脂组合物、树脂改性剂和成型体 |
| KR20100015432A (ko) * | 2007-03-09 | 2010-02-12 | 바스프 에스이 | 리튬-이온 전지용 니트록시드 |
| MX2009010535A (es) * | 2007-04-05 | 2009-10-22 | Basf Se | Protector solar y composiciones para el cuidado personal que comprenden un copolimero seleccionado. |
| DE102007019131A1 (de) | 2007-04-20 | 2008-10-23 | Tesa Ag | Doppelseitiges Haftklebeband |
| WO2008145595A1 (en) * | 2007-06-01 | 2008-12-04 | Basf Se | Modified printable surfaces |
| DE102007038458A1 (de) | 2007-08-14 | 2009-02-19 | Tesa Ag | Verbundelement |
| DE102007045166A1 (de) | 2007-09-20 | 2009-04-02 | Tesa Ag | Transparentes Klebeband |
| DE102007045168A1 (de) | 2007-09-20 | 2009-04-02 | Tesa Ag | Transparentes Klebeband |
| DE102007062447A1 (de) | 2007-12-20 | 2009-06-25 | Tesa Ag | Doppelseitiges Haftklebeband für Flüssigkristallanzeigesysteme |
| WO2009149029A2 (en) * | 2008-06-04 | 2009-12-10 | The Procter & Gamble Company | Denture adhesive compositions and methods |
| KR101315543B1 (ko) | 2009-01-08 | 2013-10-08 | 바스프 에스이 | 중합 개시제 |
| DE102009006593A1 (de) | 2009-01-29 | 2010-08-05 | Tesa Se | Verfahren zur Korrosionsschutzbehandlung von Metalloberflächen |
| DE102009007589A1 (de) | 2009-02-05 | 2010-08-12 | Tesa Se | Transfer-Haftklebeband sowie Verfahren zur Herstellung eines Haftklebebandes |
| JP5706886B2 (ja) | 2009-06-12 | 2015-04-22 | スリーエム イノベイティブ プロパティズ カンパニー | フッ素化芳香族ビス（アシル）含有化合物及びそれから調製されるポリエステル |
| WO2012000992A1 (en) | 2010-06-29 | 2012-01-05 | Basf Se | Process for improving the flow properties of polymer melts |
| DE102011077927A1 (de) | 2011-06-21 | 2012-12-27 | Tesa Se | Verfahren zur reversiblen kovalenten Vernetzung von Klebemassen |
| US20140298591A1 (en) | 2011-10-25 | 2014-10-09 | Basf Se | Use of comb or block copolymers as soil antiredeposition agents and soil release agents in laundry processes |
| DE102012208597B4 (de) | 2012-05-23 | 2018-05-30 | Tesa Se | Haftklebemasse für medizinische Zwecke, Verfahren zu ihrer Herstellung und die Haftklebmasse enthaltende Mischung |
| DE102012212883A1 (de) | 2012-07-23 | 2014-05-15 | Tesa Se | Geschäumtes Klebeband zur Verklebung auf unpolaren Oberflächen |
| KR20150135489A (ko) | 2013-03-27 | 2015-12-02 | 바스프 에스이 | 세탁 과정에서 오염물 방출제로서 블록 공중합체 |
| DE102013224774A1 (de) | 2013-12-03 | 2015-06-03 | Tesa Se | Mehrschichtiges Produkt |
| DE102015222028A1 (de) | 2015-11-09 | 2017-05-11 | Tesa Se | Kationisch polymerisierbare Polyacrylate enthaltend Alkoxysilangruppen und deren Verwendung |
| DE102016207540A1 (de) | 2016-05-02 | 2017-11-02 | Tesa Se | Wasserdampfsperrende Klebemasse mit hochfunktionalisiertem Poly(meth)acrylat |
| DE102016207548A1 (de) | 2016-05-02 | 2017-11-02 | Tesa Se | Härtbare Klebemasse und darauf basierende Reaktivklebebänder |
| DE102016207550A1 (de) | 2016-05-02 | 2017-11-02 | Tesa Se | Funktionalisierte (Co)Polymere für Klebesysteme und Klebebänder |
| WO2018095926A1 (de) * | 2016-11-22 | 2018-05-31 | Sika Technology Ag | Herstellung von dispergiermitteln durch nitroxid-vermittelte lösungspolymerisation |
| DE102017223147A1 (de) | 2017-12-19 | 2019-06-19 | Tesa Se | Oberflächenschutzfolie mit Schaumschicht |
| DE102018216868A1 (de) | 2018-10-01 | 2020-04-02 | Tesa Se | Latent reaktiver Klebefilm |
| DE102019215890A1 (de) | 2019-10-16 | 2021-04-22 | Tesa Se | Härtbare Klebemasse und darauf basierende Reaktivklebebänder |
| DE102019219166B4 (de) | 2019-12-09 | 2023-08-24 | Tesa Se | Strukturelle Haftklebemasse und ihre Verwendung |
| DE102020203952A1 (de) | 2020-03-26 | 2021-09-30 | Tesa Se | Latent reaktiver Klebefilm |
| CN116490535A (zh) | 2020-11-30 | 2023-07-25 | 巴斯夫欧洲公司 | 制备聚合物分散体的方法 |
| WO2022200398A1 (en) | 2021-03-26 | 2022-09-29 | Basf Se | Polymer composition comprising polyacrylic block copolymer and aromatic based polyalkyleneoxide as dispersant |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1134946A (zh) * | 1995-02-07 | 1996-11-06 | 埃尔夫阿托化学有限公司 | 利用稳定自由基稳定聚合物 |
| WO1998030601A2 (en) * | 1997-01-10 | 1998-07-16 | E.I. Du Pont De Nemours And Company | Method of controlling polymer molecular weight and structure |
| WO1998044008A1 (en) * | 1997-03-31 | 1998-10-08 | The B.F. Goodrich Company | Controlled free radical polymerization process |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3532703A (en) * | 1966-06-15 | 1970-10-06 | Sankyo Co | 2,2,5,5-tetrasubstituted-4-oxoimidazolidine-1-oxides |
| DE1299627B (de) * | 1966-08-31 | 1969-07-24 | Dynamit Nobel Ag | Verfahren zur Herstellung von reinster Terepthalsaeure |
| JPS462905B1 (enExample) * | 1967-11-28 | 1971-01-25 | ||
| JPS5010281B1 (enExample) * | 1970-03-20 | 1975-04-19 | ||
| KR930000892B1 (ko) * | 1983-07-11 | 1993-02-11 | 커몬웰스 사이언티픽 앤드 인더스트리얼 리셔치 오가니제이숀 | 신규의 개시제를 사용하여 중합체 또는 공중합체를 제조하는방법 |
| AU571240B2 (en) * | 1983-07-11 | 1988-04-14 | Commonwealth Scientific And Industrial Research Organisation | Alkoxy-amines, useful as initiators |
| US5608023A (en) | 1995-03-30 | 1997-03-04 | Xerox Corporation | Rate enhanced polymerization processes |
| DE69708896T2 (de) * | 1996-09-25 | 2002-06-20 | Akzo Nobel N.V., Arnheim/Arnhem | Nitroso verbindungen zur pseudo-lebenden radikalpolymerisation |
| TW557313B (en) * | 1998-02-02 | 2003-10-11 | Ciba Sc Holding Ag | Oxopiperazinyl derivatives and light stabilized compositions |
| CH693416A5 (de) | 1998-03-09 | 2003-07-31 | Ciba Sc Holding Ag | 1-Alkoxypolyalkylpiperidinderivate und ihre Verwendung als Polymerisationsregler. |
| 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 |
| TW482806B (en) * | 1998-06-02 | 2002-04-11 | Ciba Sc Holding Ag | Compositions stabilized by dioxopiperazinyl derivatives |
| TW541303B (en) | 2000-03-22 | 2003-07-11 | Ciba Sc Holding Ag | 2,2,6,6 diethyl-dimethyl-1-alkoxy-piperidine compounds and their corresponding 1-oxides |
-
1999
- 1999-08-30 TW TW088115002A patent/TWI225483B/zh active
- 1999-10-06 GB GB9923579A patent/GB2342649B/en not_active Expired - Fee Related
- 1999-10-06 SE SE9903593A patent/SE522619C2/sv not_active IP Right Cessation
- 1999-10-11 NL NL1013259A patent/NL1013259C2/nl not_active IP Right Cessation
- 1999-10-12 BE BE9900673A patent/BE1012727A5/fr not_active IP Right Cessation
- 1999-10-12 AU AU53617/99A patent/AU769061B2/en not_active Ceased
- 1999-10-12 IT IT1999MI002125A patent/IT1313663B1/it active
- 1999-10-13 DE DE19949352.9A patent/DE19949352B4/de not_active Expired - Lifetime
- 1999-10-13 DK DK199901463A patent/DK199901463A/da not_active Application Discontinuation
- 1999-10-14 ES ES009902254A patent/ES2178908B1/es not_active Expired - Fee Related
- 1999-10-14 FR FR9912810A patent/FR2784684B1/fr not_active Expired - Lifetime
- 1999-10-14 US US09/417,538 patent/US6479608B1/en not_active Expired - Lifetime
- 1999-10-14 CA CA002286375A patent/CA2286375A1/en not_active Abandoned
- 1999-10-14 KR KR1019990044561A patent/KR100597892B1/ko not_active Expired - Fee Related
- 1999-10-15 BR BR9904685-7A patent/BR9904685A/pt not_active Application Discontinuation
- 1999-10-15 CN CNB991213904A patent/CN100343285C/zh not_active Expired - Fee Related
- 1999-10-15 JP JP29369799A patent/JP4895416B2/ja not_active Expired - Lifetime
-
2002
- 2002-07-09 US US10/191,193 patent/US6664353B2/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1134946A (zh) * | 1995-02-07 | 1996-11-06 | 埃尔夫阿托化学有限公司 | 利用稳定自由基稳定聚合物 |
| WO1998030601A2 (en) * | 1997-01-10 | 1998-07-16 | E.I. Du Pont De Nemours And Company | Method of controlling polymer molecular weight and structure |
| WO1998044008A1 (en) * | 1997-03-31 | 1998-10-08 | The B.F. Goodrich Company | Controlled free radical polymerization process |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2178908B1 (es) | 2004-04-01 |
| SE522619C2 (sv) | 2004-02-24 |
| FR2784684A1 (fr) | 2000-04-21 |
| SE9903593L (sv) | 2000-04-17 |
| TWI225483B (en) | 2004-12-21 |
| JP4895416B2 (ja) | 2012-03-14 |
| ITMI992125A0 (it) | 1999-10-12 |
| SE9903593D0 (sv) | 1999-10-06 |
| AU5361799A (en) | 2000-04-20 |
| US6664353B2 (en) | 2003-12-16 |
| BR9904685A (pt) | 2000-11-28 |
| AU769061B2 (en) | 2004-01-15 |
| DE19949352A1 (de) | 2000-04-20 |
| NL1013259C2 (nl) | 2000-11-21 |
| GB9923579D0 (en) | 1999-12-08 |
| FR2784684B1 (fr) | 2001-01-26 |
| JP2000128869A (ja) | 2000-05-09 |
| CN1253954A (zh) | 2000-05-24 |
| CA2286375A1 (en) | 2000-04-16 |
| IT1313663B1 (it) | 2002-09-09 |
| BE1012727A5 (fr) | 2001-02-06 |
| US20030125494A1 (en) | 2003-07-03 |
| ES2178908A1 (es) | 2003-01-01 |
| DE19949352B4 (de) | 2015-05-28 |
| DK199901463A (da) | 2000-04-17 |
| US6479608B1 (en) | 2002-11-12 |
| KR20000029079A (ko) | 2000-05-25 |
| GB2342649B (en) | 2001-07-18 |
| GB2342649A (en) | 2000-04-19 |
| KR100597892B1 (ko) | 2006-07-06 |
| ITMI992125A1 (it) | 2001-04-12 |
| NL1013259A1 (nl) | 2000-04-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1253954A (zh) | 在受控的自由基聚合方法中作为调节剂的杂环烷氧基胺 | |
| CN1171871C (zh) | 1-烷氧基-多烷基-哌啶衍生物及其作为聚合调节剂的用途 | |
| CN1302002C (zh) | 作为聚合引发剂的羟胺酯类 | |
| CN1137172C (zh) | 通过受控自由基聚合反应合成嵌段聚合物的方法 | |
| CN1134455C (zh) | 催化聚合反应方法 | |
| CN1202085C (zh) | 空间位阻的胺醚的制备 | |
| CN1214018C (zh) | 作为光稳定剂的吗啉酮化合物 | |
| CN1802409A (zh) | 颜料分散体中的光稳定聚合物分散剂 | |
| CN1231470C (zh) | N－烷氧基－4,4－二氧基－多烷基－哌啶类化合物作为自由基聚合引发剂 | |
| CN86100090A (zh) | 萘衍生物的制备方法 | |
| CN1037327A (zh) | 制备2，3-二氟代苯类的方法 | |
| CN1249035C (zh) | 4－亚氨基－n－烷氧基或氧基－多烷基－哌啶化合物以及它们作为聚合调节剂的用途 | |
| CN1430605A (zh) | 由仲氨基氧化物合成胺醚的方法 | |
| CN1222565C (zh) | 稳定剂混合物 | |
| CN1432041A (zh) | 稳定剂混合物 | |
| CN1198851C (zh) | N－烷氧基－4,4－二氧基－聚烷基－哌啶化合物、其相应的n－氧化物及其受控自由基聚合反应 | |
| CN1255383C (zh) | 基于多烷基哌啶、多烷基哌嗪酮和多烷基吗啉酮的多官能烷氧基胺以及它们作为聚合调节剂/引发剂的用途 | |
| CN1132196A (zh) | 双酚酯衍生物 | |
| CN1214028C (zh) | 可用作有机材料的稳定剂的含有1－烃氧基－2,2,6,6－四甲基－4－哌啶基基团的嵌段低聚物 | |
| CN1279065C (zh) | 用于受控的低温自由基聚合的开链烷氧基胺以及其相应的氮氧化物 | |
| CN1955238A (zh) | 低聚双乙酰乙酸烷撑二酯金属螯合物涂料催干剂及制备与应用 | |
| CN1420871A (zh) | 4－甲酰氨基－n－甲基哌啶衍生物、其作为稳定剂的应用和所得的稳定化有机物质 | |
| CN1163278A (zh) | (甲基)丙烯基与乙烯基单体的受控制的聚合或共聚合方法及其产品 | |
| CN1241913C (zh) | 制备2－苯基－3－萘基丙酸衍生物的方法 | |
| CN1061970A (zh) | 具有降压和血管舒张活性的苯并吡喃衍生物、其制法及其治疗效用 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |