ES2316167T3 - Dreivados de 1-oxil-2,2,6,6-tetrametil-4-hidroxipiperidina como inhibidores de monomeeros (met) acrilato. - Google Patents
Dreivados de 1-oxil-2,2,6,6-tetrametil-4-hidroxipiperidina como inhibidores de monomeeros (met) acrilato. Download PDFInfo
- Publication number
- ES2316167T3 ES2316167T3 ES98936423T ES98936423T ES2316167T3 ES 2316167 T3 ES2316167 T3 ES 2316167T3 ES 98936423 T ES98936423 T ES 98936423T ES 98936423 T ES98936423 T ES 98936423T ES 2316167 T3 ES2316167 T3 ES 2316167T3
- Authority
- ES
- Spain
- Prior art keywords
- unsaturated
- oxyl
- acid
- monomer
- water
- 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 - Lifetime
Links
- 239000003112 inhibitor Substances 0.000 title description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title description 3
- 239000000178 monomer Substances 0.000 claims abstract description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 32
- 239000002253 acid Substances 0.000 claims abstract description 20
- 230000002028 premature Effects 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 150000001408 amides Chemical class 0.000 claims abstract description 12
- 230000000087 stabilizing effect Effects 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 150000002170 ethers Chemical class 0.000 claims abstract description 7
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims abstract description 7
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 150000002825 nitriles Chemical class 0.000 claims abstract description 6
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 claims abstract description 6
- -1 2-methoxyethoxymethyl Chemical group 0.000 claims description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 21
- 150000002148 esters Chemical class 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 11
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 10
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 9
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 7
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 6
- DREPONDJUKIQLX-UHFFFAOYSA-N 1-[ethenyl(ethoxy)phosphoryl]oxyethane Chemical compound CCOP(=O)(C=C)OCC DREPONDJUKIQLX-UHFFFAOYSA-N 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000006309 butyl amino group Chemical group 0.000 claims description 2
- SKKTUOZKZKCGTB-UHFFFAOYSA-N butyl carbamate Chemical compound CCCCOC(N)=O SKKTUOZKZKCGTB-UHFFFAOYSA-N 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
- 238000010348 incorporation Methods 0.000 claims 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-L ethenyl-dioxido-oxo-$l^{5}-phosphane Chemical compound [O-]P([O-])(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-L 0.000 abstract 1
- CSGAUKGQUCHWDP-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1O CSGAUKGQUCHWDP-UHFFFAOYSA-N 0.000 description 15
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 230000006641 stabilisation Effects 0.000 description 8
- 238000011105 stabilization Methods 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- YYTYIUAYFBFKHX-UHFFFAOYSA-N n-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)acetamide Chemical compound CC(=O)NC1CC(C)(C)N(O)C(C)(C)C1 YYTYIUAYFBFKHX-UHFFFAOYSA-N 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000012085 test solution Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000005215 alkyl ethers Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000005192 partition Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000012086 standard solution Substances 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- JLIJWDAZRLBHGX-UHFFFAOYSA-N methyl 2-(2-methoxyethoxy)acetate Chemical compound COCCOCC(=O)OC JLIJWDAZRLBHGX-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- WXUAQHNMJWJLTG-VKHMYHEASA-N (S)-methylsuccinic acid Chemical compound OC(=O)[C@@H](C)CC(O)=O WXUAQHNMJWJLTG-VKHMYHEASA-N 0.000 description 1
- AYSOUYKQIUYGFR-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1O AYSOUYKQIUYGFR-UHFFFAOYSA-N 0.000 description 1
- PMTVEXBJLIRTEJ-UHFFFAOYSA-N 2-methyl-4-nitrosophenol Chemical compound CC1=CC(N=O)=CC=C1O PMTVEXBJLIRTEJ-UHFFFAOYSA-N 0.000 description 1
- JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical compound OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001253 acrylic acids Chemical class 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- WCRDXYSYPCEIAK-UHFFFAOYSA-N dibutylstannane Chemical compound CCCC[SnH2]CCCC WCRDXYSYPCEIAK-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 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
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical class O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
- 238000010998 test method Methods 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
- C07B63/04—Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/50—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/62—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP1998/004382 WO2000003965A1 (en) | 1998-07-14 | 1998-07-14 | Derivatives of 1-oxyl-4-hydroxy- or 4-amino-2,2,6,6-tetramethylpiperidine as polymerization inhibitors for (meth)acrylate monomers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2316167T3 true ES2316167T3 (es) | 2009-04-01 |
Family
ID=8167003
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES98936423T Expired - Lifetime ES2316167T3 (es) | 1998-07-14 | 1998-07-14 | Dreivados de 1-oxil-2,2,6,6-tetrametil-4-hidroxipiperidina como inhibidores de monomeeros (met) acrilato. |
| ES08168030T Expired - Lifetime ES2364724T3 (es) | 1998-07-14 | 1998-07-14 | Derivados de 1-oxil-4-hidroxi-2,2,6,6-tetrametilpiperidina como inhibidores de la polimerización de monómeros de (met)acrilato. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES08168030T Expired - Lifetime ES2364724T3 (es) | 1998-07-14 | 1998-07-14 | Derivados de 1-oxil-4-hidroxi-2,2,6,6-tetrametilpiperidina como inhibidores de la polimerización de monómeros de (met)acrilato. |
Country Status (8)
| Country | Link |
|---|---|
| EP (2) | EP2030963B1 (enExample) |
| JP (1) | JP4499919B2 (enExample) |
| KR (1) | KR20010106405A (enExample) |
| AU (1) | AU8542498A (enExample) |
| CA (1) | CA2337032C (enExample) |
| DE (1) | DE69840389D1 (enExample) |
| ES (2) | ES2316167T3 (enExample) |
| WO (1) | WO2000003965A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100417098B1 (ko) * | 1998-07-27 | 2004-02-05 | 니폰 쇼쿠바이 컴파니 리미티드 | 비닐 화합물의 중합 억제 방법 |
| JP3863694B2 (ja) * | 1999-12-24 | 2006-12-27 | 株式会社日本触媒 | ビニル化合物中のｎ−オキシル化合物の安定化方法 |
| 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 |
| CN1697808A (zh) * | 2003-12-24 | 2005-11-16 | 三菱化学株式会社 | (甲基)丙烯酸混合物聚合性的评价方法 |
| ES2317123T5 (es) | 2005-09-27 | 2017-05-05 | Nestec S.A. | Módulo de extracción para un dispositivo de producción de bebidas a partir de cápsulas |
| JP4961176B2 (ja) * | 2006-07-31 | 2012-06-27 | 三菱レイヨン株式会社 | 含酸素アルコール残基を有する（メタ）アクリル酸エステル用重合防止剤および該（メタ）アクリル酸エステルの混合物 |
| JP5191702B2 (ja) * | 2006-08-01 | 2013-05-08 | 三菱レイヨン株式会社 | Ｎ−オキシル化合物、その製造方法および重合防止方法 |
| KR100891954B1 (ko) * | 2007-05-02 | 2009-04-07 | 전병준 | 비닐아세테이트 단량체 제조공정중의 중합방지방법 |
| US9399622B2 (en) | 2013-12-03 | 2016-07-26 | Ecolab Usa Inc. | Nitroxide hydroxylamine and phenylenediamine combinations as polymerization inhibitors for ethylenically unsaturated monomer processes |
| CN116410124A (zh) * | 2023-03-01 | 2023-07-11 | 烟台新特路新材料科技有限公司 | 一种含不饱和烃和自由基的自修复高分子助剂及其合成方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB1127127A (en) | 1966-04-26 | 1968-09-11 | Bp Chem Int Ltd | Stabilization of acrylic acid |
| GB1124009A (en) | 1966-04-26 | 1968-08-14 | Bp Chem Int Ltd | Polymerization of chloroprene |
| GB1346774A (en) | 1970-10-05 | 1974-02-13 | Bp Chem Int Ltd | Stabilisation of acrylonitrile |
| US4472547A (en) | 1983-06-30 | 1984-09-18 | Ciba-Geigy Corporation | N-Piperidyl lactam light stabilizers |
| JPS6036501A (ja) | 1983-08-10 | 1985-02-25 | Adeka Argus Chem Co Ltd | ビニル重合禁止剤 |
| EP0178168B1 (en) | 1984-10-10 | 1990-01-17 | Amoco Corporation | Process for purification of methacrylic acid |
| EP0467849B1 (en) * | 1990-07-20 | 1995-04-05 | Ciba-Geigy Ag | Stabilized monomer compositions |
| JP3197947B2 (ja) | 1992-05-21 | 2001-08-13 | 株式会社クラレ | （メタ）アクリル酸の重合防止法 |
| JP3227204B2 (ja) | 1992-05-21 | 2001-11-12 | 株式会社クラレ | （メタ）アクリル酸の重合防止方法 |
| US5254760A (en) | 1992-07-29 | 1993-10-19 | Ciba-Geigy Corporation | Inhibiting polymerization of vinyl aromatic monomers |
| US5322960A (en) | 1993-04-15 | 1994-06-21 | Nippon Shokubai Co., Ltd. | Method for inhibiting polymerization of (meth) acrylic acid and esters thereof |
| TW294658B (enExample) | 1994-06-02 | 1997-01-01 | Nippon Catalytic Chem Ind | |
| EP0697386B1 (de) * | 1994-08-19 | 1998-11-25 | Hüls Aktiengesellschaft | Inhibierung der Polymerisation von Styrol |
| US5545786C1 (en) | 1994-11-28 | 2001-10-16 | Ciba Geigy Corp | Method for inhibiting premature polymerization of vinyl aromatic monomers |
| DE19510184A1 (de) | 1995-03-21 | 1996-09-26 | Basf Ag | 4-Acylaminopiperidin-N-oxyle |
| EP0791573A1 (en) | 1996-02-21 | 1997-08-27 | Nalco/Exxon Chemicals Company L.P. | Nitroxides as antipolymerants for vinyl acetate units |
| DE19609312A1 (de) * | 1996-03-09 | 1997-09-11 | Basf Ag | Stabilisierte Monomerenzusammensetzung |
| JPH09268138A (ja) | 1996-04-02 | 1997-10-14 | Hakuto Co Ltd | スチレン類の重合抑制方法 |
| CZ290225B6 (cs) | 1996-05-27 | 2002-06-12 | Mitsubishi Chemical Corporation | Způsob inhibice polymerace kyseliny (meth)akrylové a jejich esterů |
| GB9614854D0 (en) * | 1996-07-15 | 1996-09-04 | Marks A H & Co Ltd | Free radical scavengers |
| US5877344A (en) * | 1997-06-13 | 1999-03-02 | Ciba Specialty Chemicals Corporation | Polymerization inhibition of acrylates using blends of nitroxides |
| JP2001510881A (ja) * | 1997-07-23 | 2001-08-07 | 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 | ニトロキシドおよび他の補助添加剤を使用するパルプおよび紙の黄色化の抑制 |
| JP4137228B2 (ja) * | 1998-04-27 | 2008-08-20 | 旭化成ケミカルズ株式会社 | メタクリル酸シクロヘキシルの製造方法 |
-
1998
- 1998-07-14 EP EP08168030A patent/EP2030963B1/en not_active Expired - Lifetime
- 1998-07-14 DE DE69840389T patent/DE69840389D1/de not_active Expired - Lifetime
- 1998-07-14 ES ES98936423T patent/ES2316167T3/es not_active Expired - Lifetime
- 1998-07-14 WO PCT/EP1998/004382 patent/WO2000003965A1/en not_active Ceased
- 1998-07-14 AU AU85424/98A patent/AU8542498A/en not_active Abandoned
- 1998-07-14 ES ES08168030T patent/ES2364724T3/es not_active Expired - Lifetime
- 1998-07-14 CA CA002337032A patent/CA2337032C/en not_active Expired - Fee Related
- 1998-07-14 EP EP98936423A patent/EP1095006B1/en not_active Expired - Lifetime
- 1998-07-14 KR KR1020017000584A patent/KR20010106405A/ko not_active Ceased
- 1998-07-14 JP JP2000560075A patent/JP4499919B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1095006B1 (en) | 2008-12-24 |
| CA2337032A1 (en) | 2000-01-27 |
| JP2002520379A (ja) | 2002-07-09 |
| EP2030963A3 (en) | 2009-05-20 |
| EP2030963B1 (en) | 2011-06-08 |
| AU8542498A (en) | 2000-02-07 |
| WO2000003965A1 (en) | 2000-01-27 |
| EP1095006A1 (en) | 2001-05-02 |
| KR20010106405A (ko) | 2001-11-29 |
| DE69840389D1 (en) | 2009-02-05 |
| ES2364724T3 (es) | 2011-09-13 |
| EP2030963A2 (en) | 2009-03-04 |
| CA2337032C (en) | 2008-12-02 |
| JP4499919B2 (ja) | 2010-07-14 |
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