ES2364724T3 - Derivados de 1-oxil-4-hidroxi-2,2,6,6-tetrametilpiperidina como inhibidores de la polimerización de monómeros de (met)acrilato. - Google Patents
Derivados de 1-oxil-4-hidroxi-2,2,6,6-tetrametilpiperidina como inhibidores de la polimerización de monómeros de (met)acrilato. Download PDFInfo
- Publication number
- ES2364724T3 ES2364724T3 ES08168030T ES08168030T ES2364724T3 ES 2364724 T3 ES2364724 T3 ES 2364724T3 ES 08168030 T ES08168030 T ES 08168030T ES 08168030 T ES08168030 T ES 08168030T ES 2364724 T3 ES2364724 T3 ES 2364724T3
- Authority
- ES
- Spain
- Prior art keywords
- polymerization
- monomers
- oxyl
- water
- derivatives
- 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
- 239000000178 monomer Substances 0.000 title description 26
- 238000006116 polymerization reaction Methods 0.000 title description 23
- 239000003112 inhibitor Substances 0.000 title description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title description 3
- -1 2-hydroxy -4-oxopentyl Chemical group 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 13
- 230000002028 premature Effects 0.000 description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 229920002554 vinyl polymer Polymers 0.000 description 9
- 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 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000006641 stabilisation Effects 0.000 description 6
- 238000011105 stabilization Methods 0.000 description 6
- 125000005395 methacrylic acid group Chemical class 0.000 description 5
- 239000012085 test solution Substances 0.000 description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 230000000087 stabilizing effect Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000005215 alkyl ethers Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000011550 stock 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
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004440 column chromatography Methods 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
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000003860 storage Methods 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- CRGBPDJWOLULDY-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) acetate Chemical compound CC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 CRGBPDJWOLULDY-UHFFFAOYSA-N 0.000 description 1
- VZSCEEGBKGDYGI-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) octanoate Chemical group CCCCCCCC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 VZSCEEGBKGDYGI-UHFFFAOYSA-N 0.000 description 1
- KKZZSTCINUMTGD-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidin-4-ol Chemical compound CC1C(O)CCN(C)C1(C)C KKZZSTCINUMTGD-UHFFFAOYSA-N 0.000 description 1
- LWWWYUBIKPGGGT-UHFFFAOYSA-N 1-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)oxy-3-methoxypropan-2-ol Chemical compound COCC(O)COC1CC(C)(C)N(O)C(C)(C)C1 LWWWYUBIKPGGGT-UHFFFAOYSA-N 0.000 description 1
- VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-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
- CDMQEZXNRWWKGT-UHFFFAOYSA-N 3-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)oxypropane-1,2-diol Chemical compound CC1(C)CC(OCC(O)CO)CC(C)(C)N1O CDMQEZXNRWWKGT-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-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
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- SXPLGYBFGPYAHS-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 SXPLGYBFGPYAHS-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 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
- 238000007796 conventional method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-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
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 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 |
|---|---|
| ES2364724T3 true ES2364724T3 (es) | 2011-09-13 |
Family
ID=8167003
Family Applications (2)
| 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. |
| 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. |
Family Applications After (1)
| 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. |
Country Status (8)
| Country | Link |
|---|---|
| EP (2) | EP2030963B1 (https=) |
| JP (1) | JP4499919B2 (https=) |
| KR (1) | KR20010106405A (https=) |
| AU (1) | AU8542498A (https=) |
| CA (1) | CA2337032C (https=) |
| DE (1) | DE69840389D1 (https=) |
| ES (2) | ES2364724T3 (https=) |
| WO (1) | WO2000003965A1 (https=) |
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 |
| WO2005061556A1 (ja) * | 2003-12-24 | 2005-07-07 | Mitsubishi Chemical Corporation | （メタ）アクリル酸混合物の重合性の評価方法 |
| 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 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| ATE49588T1 (de) | 1984-10-10 | 1990-02-15 | Amoco Corp | Verfahren zur reinigung von methacrylsaeure. |
| DE69108626T2 (de) * | 1990-07-20 | 1995-08-24 | Ciba Geigy Ag | Stabilisierte Monomerenzusammensetzungen. |
| 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 |
| 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 |
| 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 (https=) | 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 |
| DE69701590T2 (de) | 1996-05-27 | 2000-09-07 | Mitsubishi Chemical Corp., Tokio/Tokyo | Verfahren zur Polymerisationsinhibierung von (Meth-)Acrylsäure und ihrer Ester |
| 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 |
| RU2223985C2 (ru) * | 1997-07-23 | 2004-02-20 | Циба Спешиалти Кемикалз Холдинг Инк. | Ингибирование пожелтения целлюлозы и бумаги с использованием нитроксидов и других совместно вводимых добавок |
| 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 WO PCT/EP1998/004382 patent/WO2000003965A1/en not_active Ceased
- 1998-07-14 ES ES08168030T patent/ES2364724T3/es not_active Expired - Lifetime
- 1998-07-14 EP EP08168030A patent/EP2030963B1/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
- 1998-07-14 ES ES98936423T patent/ES2316167T3/es not_active Expired - Lifetime
- 1998-07-14 EP EP98936423A patent/EP1095006B1/en not_active Expired - Lifetime
- 1998-07-14 AU AU85424/98A patent/AU8542498A/en not_active Abandoned
- 1998-07-14 DE DE69840389T patent/DE69840389D1/de not_active Expired - Lifetime
- 1998-07-14 CA CA002337032A patent/CA2337032C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2316167T3 (es) | 2009-04-01 |
| DE69840389D1 (en) | 2009-02-05 |
| AU8542498A (en) | 2000-02-07 |
| EP1095006B1 (en) | 2008-12-24 |
| EP2030963A2 (en) | 2009-03-04 |
| CA2337032A1 (en) | 2000-01-27 |
| WO2000003965A1 (en) | 2000-01-27 |
| JP2002520379A (ja) | 2002-07-09 |
| EP2030963A3 (en) | 2009-05-20 |
| EP2030963B1 (en) | 2011-06-08 |
| KR20010106405A (ko) | 2001-11-29 |
| CA2337032C (en) | 2008-12-02 |
| EP1095006A1 (en) | 2001-05-02 |
| JP4499919B2 (ja) | 2010-07-14 |
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