RU2116285C1 - Композиция, предупреждающая преждевременную полимеризацию винилароматических соединений, и способ предупреждения полимеризации винилароматических соединений - Google Patents
Композиция, предупреждающая преждевременную полимеризацию винилароматических соединений, и способ предупреждения полимеризации винилароматических соединений Download PDFInfo
- Publication number
- RU2116285C1 RU2116285C1 RU93048468A RU93048468A RU2116285C1 RU 2116285 C1 RU2116285 C1 RU 2116285C1 RU 93048468 A RU93048468 A RU 93048468A RU 93048468 A RU93048468 A RU 93048468A RU 2116285 C1 RU2116285 C1 RU 2116285C1
- Authority
- RU
- Russia
- Prior art keywords
- oxyl
- tetramethylpiperidin
- compound
- bis
- inhibitor
- Prior art date
Links
- -1 vinyl aromatic compounds Chemical class 0.000 title claims abstract description 119
- 239000000203 mixture Substances 0.000 title claims abstract description 47
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 46
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims description 36
- 230000002028 premature Effects 0.000 title claims description 10
- 230000002265 prevention Effects 0.000 title 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 46
- 238000004821 distillation Methods 0.000 claims abstract description 37
- 239000003112 inhibitor Substances 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 28
- 238000000746 purification Methods 0.000 claims description 16
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 12
- HOYRZHJJAHRMLL-UHFFFAOYSA-N 2,6-dinitro-p-cresol Chemical compound CC1=CC([N+]([O-])=O)=C(O)C([N+]([O-])=O)=C1 HOYRZHJJAHRMLL-UHFFFAOYSA-N 0.000 claims description 10
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 10
- SYDNSSSQVSOXTN-UHFFFAOYSA-N 2-nitro-p-cresol Chemical compound CC1=CC=C(O)C([N+]([O-])=O)=C1 SYDNSSSQVSOXTN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 claims description 7
- BGLKXHNUOPUFCL-UHFFFAOYSA-N 4-hydroxy-1-[2-(4-hydroxy-3,3,5,5-tetramethyl-2-oxopiperazin-1-yl)ethyl]-3,3,5,5-tetramethylpiperazin-2-one Chemical compound O=C1C(C)(C)N(O)C(C)(C)CN1CCN1C(=O)C(C)(C)N(O)C(C)(C)C1 BGLKXHNUOPUFCL-UHFFFAOYSA-N 0.000 claims description 7
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 7
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 6
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 claims description 5
- DRFYZAIGLPMIOS-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) benzoate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)C1=CC=CC=C1 DRFYZAIGLPMIOS-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- KMEUSKGEUADGET-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)N1O KMEUSKGEUADGET-UHFFFAOYSA-N 0.000 claims description 4
- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical compound CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 claims description 4
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 claims description 4
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 claims description 3
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 claims description 3
- UOQOHSUPANZDSJ-UHFFFAOYSA-N 2-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)C1CC(C)(C)N(O)C(C)(C)C1 UOQOHSUPANZDSJ-UHFFFAOYSA-N 0.000 claims description 3
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 claims description 3
- JPHYFFRXJKGOED-UHFFFAOYSA-N 3-dodecyl-1-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidine-2,5-dione Chemical compound O=C1C(CCCCCCCCCCCC)CC(=O)N1C1CC(C)(C)N(O)C(C)(C)C1 JPHYFFRXJKGOED-UHFFFAOYSA-N 0.000 claims description 3
- INBLGVOPOSGVTA-UHFFFAOYSA-N 4-hydroxy-3-nitrobenzonitrile Chemical compound OC1=CC=C(C#N)C=C1[N+]([O-])=O INBLGVOPOSGVTA-UHFFFAOYSA-N 0.000 claims description 3
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 claims description 3
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 claims description 3
- WJZRRMYMGWLZDY-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) benzene-1,2-dicarboxylate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)C1=CC=CC=C1C(=O)OC1CC(C)(C)N(O)C(C)(C)C1 WJZRRMYMGWLZDY-UHFFFAOYSA-N 0.000 claims description 3
- YJLOZVIELWKSNE-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) benzene-1,3-dicarboxylate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)C1=CC=CC(C(=O)OC2CC(C)(C)N(O)C(C)(C)C2)=C1 YJLOZVIELWKSNE-UHFFFAOYSA-N 0.000 claims description 3
- ZXDIQRGIYADNBI-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) butanedioate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)CCC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 ZXDIQRGIYADNBI-UHFFFAOYSA-N 0.000 claims description 3
- GITLFISGTYWQIU-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) cyclohexane-1,4-dicarboxylate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)C1CCC(C(=O)OC2CC(C)(C)N(O)C(C)(C)C2)CC1 GITLFISGTYWQIU-UHFFFAOYSA-N 0.000 claims description 3
- SIXHNVLZVKYFOR-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) hexanedioate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)CCCCC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 SIXHNVLZVKYFOR-UHFFFAOYSA-N 0.000 claims description 3
- CKJMHSMEPSUICM-UHFFFAOYSA-N di-tert-butyl nitroxide Chemical group CC(C)(C)N([O])C(C)(C)C CKJMHSMEPSUICM-UHFFFAOYSA-N 0.000 claims description 3
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 claims description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical class O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims 6
- 229940125773 compound 10 Drugs 0.000 claims 4
- 229940125810 compound 20 Drugs 0.000 claims 4
- 108010041382 compound 20 Proteins 0.000 claims 4
- 229940125898 compound 5 Drugs 0.000 claims 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims 4
- FYFDQJRXFWGIBS-UHFFFAOYSA-N 1,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C([N+]([O-])=O)C=C1 FYFDQJRXFWGIBS-UHFFFAOYSA-N 0.000 claims 2
- MYKPPUUOBUFFML-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) benzene-1,4-dicarboxylate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)C1=CC=C(C(=O)OC2CC(C)(C)N(O)C(C)(C)C2)C=C1 MYKPPUUOBUFFML-UHFFFAOYSA-N 0.000 claims 2
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 claims 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims 2
- 150000002828 nitro derivatives Chemical class 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 8
- 230000005764 inhibitory process Effects 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 241001676573 Minium Species 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 description 16
- 239000004793 Polystyrene Substances 0.000 description 12
- 229920002223 polystyrene Polymers 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 9
- 239000000178 monomer Substances 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000002195 synergetic effect Effects 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YLFIGGHWWPSIEG-UHFFFAOYSA-N aminoxyl Chemical compound [O]N YLFIGGHWWPSIEG-UHFFFAOYSA-N 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
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 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
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- LQZRWOYCCOIIAQ-UHFFFAOYSA-N 1,3-dinitrobenzene;1,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C([N+]([O-])=O)C=C1.[O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 LQZRWOYCCOIIAQ-UHFFFAOYSA-N 0.000 description 1
- DSSWUSNSRXWFBO-UHFFFAOYSA-N 1-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)azepan-2-one Chemical compound C1C(C)(C)N(O)C(C)(C)CC1N1C(=O)CCCCC1 DSSWUSNSRXWFBO-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- HVRXHOKJHFUMDT-UHFFFAOYSA-N 4-hydroxy-2-iodo-6-nitrobenzonitrile Chemical compound OC1=CC(I)=C(C#N)C([N+]([O-])=O)=C1 HVRXHOKJHFUMDT-UHFFFAOYSA-N 0.000 description 1
- ZULAQTMCHQGOMI-UHFFFAOYSA-N CC(C)(C)C1=CC=C(C(O)=O)C(C2CC(C)(C)N(O)C(C)(C)C2)=C1 Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C(C2CC(C)(C)N(O)C(C)(C)C2)=C1 ZULAQTMCHQGOMI-UHFFFAOYSA-N 0.000 description 1
- YQBVXLOPZJSBRD-UHFFFAOYSA-N CCCCC(CC)(C(O)=O)C1CC(C)(C)N(O)C(C)(C)C1 Chemical compound CCCCC(CC)(C(O)=O)C1CC(C)(C)N(O)C(C)(C)C1 YQBVXLOPZJSBRD-UHFFFAOYSA-N 0.000 description 1
- UBUCNCOMADRQHX-UHFFFAOYSA-N N-Nitrosodiphenylamine Chemical compound C=1C=CC=CC=1N(N=O)C1=CC=CC=C1 UBUCNCOMADRQHX-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 231100000916 relative toxicity Toxicity 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- 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
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/921,824 US5254760A (en) | 1992-07-29 | 1992-07-29 | Inhibiting polymerization of vinyl aromatic monomers |
| US07/921824 | 1992-07-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU93048468A RU93048468A (ru) | 1997-01-20 |
| RU2116285C1 true RU2116285C1 (ru) | 1998-07-27 |
Family
ID=25446025
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU93048468A RU2116285C1 (ru) | 1992-07-29 | 1993-07-12 | Композиция, предупреждающая преждевременную полимеризацию винилароматических соединений, и способ предупреждения полимеризации винилароматических соединений |
Country Status (14)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2268871C1 (ru) * | 2004-09-20 | 2006-01-27 | Открытое акционерное общество "Нижнекамскнефтехим" | Способ выделения стирола |
| RU2391328C2 (ru) * | 2004-12-03 | 2010-06-10 | Кемтура Корпорейшн | Ароматические сульфоновые кислоты, амины и нитрофенолы в комбинации с соединениями, содержащими нитроксильный радикал, или с с-нитрозоанилинами в качестве ингибиторов полимеризации |
Families Citing this family (88)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW294658B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) † | 1994-06-02 | 1997-01-01 | Nippon Catalytic Chem Ind | |
| US5728872A (en) * | 1994-06-27 | 1998-03-17 | Lutz Riemenschneider | Stabilized acrylic acid compositions |
| EP0697386B1 (de) * | 1994-08-19 | 1998-11-25 | Hüls Aktiengesellschaft | Inhibierung der Polymerisation von Styrol |
| US5888356A (en) * | 1994-08-19 | 1999-03-30 | Huels Aktiengesellschaft | Inhibition of polymerization of vinylaromatic or vinylaliphatic |
| 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 |
| US5616774A (en) * | 1995-04-14 | 1997-04-01 | Ciba-Geigy Corporation | Inhibition of unsaturated monomers with 7-aryl quinone methides |
| DE19531649A1 (de) * | 1995-08-29 | 1997-03-06 | Basf Ag | Dübelmasse für die chemische Befestigungstechnik |
| US5629426A (en) * | 1995-11-09 | 1997-05-13 | Ciba-Geigy Corporation | Carbonate-mediated hydrogen peroxide oxidations of 4-hydroxy-2,2,6,6-tetramethylpiperidine |
| US5654434A (en) * | 1995-11-09 | 1997-08-05 | Ciba-Geigy Corporation | Hydrogen peroxide oxidation of 4-hydroxy-2, 2, 6, 6-tetramethylpiperidine |
| DE19609312A1 (de) * | 1996-03-09 | 1997-09-11 | Basf Ag | Stabilisierte Monomerenzusammensetzung |
| US5777126A (en) * | 1996-05-01 | 1998-07-07 | Ciba Specialty Chemicals Corporation | Carbonate-mediated hydrogen peroxide oxidation of 4-acylamino-2,2,6,6-tetramethylpiperidine |
| WO1997046504A1 (de) * | 1996-06-05 | 1997-12-11 | Basf Aktiengesellschaft | Mischungen, enthaltend monomere und stabilisatoren |
| US5711767A (en) * | 1996-07-11 | 1998-01-27 | Ciba Specialty Chemicals Corporation | Stabilizers for the prevention of gum formation in gasoline |
| GB9614854D0 (en) * | 1996-07-15 | 1996-09-04 | Marks A H & Co Ltd | Free radical scavengers |
| US6409887B1 (en) | 1996-07-15 | 2002-06-25 | Aah Marks And Company Limited | Polymerization inhibitor |
| DE19638868A1 (de) * | 1996-09-23 | 1998-03-26 | Basf Ag | Stabilisierte Monomerenzusammensetzung |
| EP0845448B1 (en) * | 1996-12-02 | 2002-01-30 | Ondeo Nalco Energy Services, L.P. | Inhibiting polymerization of vinyl aromatic monomers |
| DE19651307A1 (de) | 1996-12-10 | 1998-06-18 | Basf Ag | Stoffmischungen, enthaltend vinylgruppenhaltige Verbindungen und Stabilisatoren |
| US5847035A (en) * | 1997-03-13 | 1998-12-08 | Uniroyal Chemical Company, Inc. | Substituteed tetrahydropyrimidine derivatives and their use as polymerization inhibitors for vinyl aromatic compounds |
| DE19811602A1 (de) * | 1997-03-20 | 1998-11-12 | Ciba Geigy Ag | Polymerisationsinhibitor-Verfahren |
| US6281311B1 (en) * | 1997-03-31 | 2001-08-28 | Pmd Holdings Corp. | Controlled free radical polymerization process |
| US5932735A (en) * | 1997-06-13 | 1999-08-03 | Ciba Specialty Chemicals Corporation | Derivatives of 1-oxyl-4-hydroxy-2,2,6,6-tetramethylpiperidine as polymerization inhibitors for (meth)acrylate monomers |
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- 1993-07-28 KR KR1019930014662A patent/KR0177045B1/ko not_active Expired - Lifetime
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- 1993-07-28 CN CN93108469A patent/CN1041513C/zh not_active Expired - Lifetime
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| RU2268871C1 (ru) * | 2004-09-20 | 2006-01-27 | Открытое акционерное общество "Нижнекамскнефтехим" | Способ выделения стирола |
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Also Published As
| Publication number | Publication date |
|---|---|
| TW226023B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1994-07-01 |
| EP0581737A2 (en) | 1994-02-02 |
| AU666024B2 (en) | 1996-01-25 |
| CN1084155A (zh) | 1994-03-23 |
| EP0581737B1 (en) | 1997-04-23 |
| CN1041513C (zh) | 1999-01-06 |
| MX9304506A (es) | 1994-01-31 |
| BR9303023A (pt) | 1994-03-15 |
| KR940005687A (ko) | 1994-03-22 |
| EP0581737A3 (en) | 1995-06-21 |
| CA2101359A1 (en) | 1994-01-30 |
| KR0177045B1 (ko) | 1999-05-15 |
| SA93140161B1 (ar) | 2005-06-13 |
| DE69310044T2 (de) | 1997-11-20 |
| AU4425093A (en) | 1994-02-03 |
| DE69310044D1 (de) | 1997-05-28 |
| JP2855399B2 (ja) | 1999-02-10 |
| US5254760A (en) | 1993-10-19 |
| CA2101359C (en) | 2001-03-20 |
| JPH06166636A (ja) | 1994-06-14 |
| ES2101995T3 (es) | 1997-07-16 |
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