JP3544985B2 - ビニル化合物の重合防止方法 - Google Patents
ビニル化合物の重合防止方法 Download PDFInfo
- Publication number
- JP3544985B2 JP3544985B2 JP50936796A JP50936796A JP3544985B2 JP 3544985 B2 JP3544985 B2 JP 3544985B2 JP 50936796 A JP50936796 A JP 50936796A JP 50936796 A JP50936796 A JP 50936796A JP 3544985 B2 JP3544985 B2 JP 3544985B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- copper
- vinyl compound
- acrylic acid
- polymerization
- 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
- 238000006116 polymerization reaction Methods 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 24
- 230000003405 preventing effect Effects 0.000 title claims description 15
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 45
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 45
- -1 vinyl compound Chemical class 0.000 claims description 36
- 229920002554 vinyl polymer Polymers 0.000 claims description 33
- 238000005260 corrosion Methods 0.000 claims description 23
- 230000007797 corrosion Effects 0.000 claims description 23
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 17
- 239000002184 metal Substances 0.000 claims description 17
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000003112 inhibitor Substances 0.000 claims description 14
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 11
- 239000012990 dithiocarbamate Substances 0.000 claims description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 10
- 150000007522 mineralic acids Chemical class 0.000 claims description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
- KGGZTXSNARMULX-UHFFFAOYSA-L copper;dicarbamodithioate Chemical compound [Cu+2].NC([S-])=S.NC([S-])=S KGGZTXSNARMULX-UHFFFAOYSA-L 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004327 boric acid Substances 0.000 claims description 3
- 150000004715 keto acids Chemical class 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- UBONKQIVJMCFNM-UHFFFAOYSA-L copper;n,n-dibutylcarbamothioate Chemical group [Cu+2].CCCCN(C([O-])=S)CCCC.CCCCN(C([O-])=S)CCCC UBONKQIVJMCFNM-UHFFFAOYSA-L 0.000 claims 2
- 230000000052 comparative effect Effects 0.000 description 27
- IXPUJMULXNNEHS-UHFFFAOYSA-L copper;n,n-dibutylcarbamodithioate Chemical compound [Cu+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC IXPUJMULXNNEHS-UHFFFAOYSA-L 0.000 description 16
- 230000004580 weight loss Effects 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 7
- 238000004821 distillation Methods 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000001879 copper Chemical class 0.000 description 4
- 229910052748 manganese Inorganic materials 0.000 description 4
- 239000011572 manganese Substances 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- 159000000014 iron salts Chemical class 0.000 description 3
- 150000002815 nickel Chemical class 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- 150000003751 zinc Chemical class 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- VWNVWFBBRCCUPA-UHFFFAOYSA-N C(CCCC)SC(NC1=CC=CC=C1)=S Chemical compound C(CCCC)SC(NC1=CC=CC=C1)=S VWNVWFBBRCCUPA-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 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
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OBBCYCYCTJQCCK-UHFFFAOYSA-L copper;n,n-diethylcarbamodithioate Chemical compound [Cu+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S OBBCYCYCTJQCCK-UHFFFAOYSA-L 0.000 description 1
- WIIJVOHQGQETTP-UHFFFAOYSA-L copper;n,n-dihexylcarbamodithioate Chemical compound [Cu+2].CCCCCCN(C([S-])=S)CCCCCC.CCCCCCN(C([S-])=S)CCCCCC WIIJVOHQGQETTP-UHFFFAOYSA-L 0.000 description 1
- ZOUQIAGHKFLHIA-UHFFFAOYSA-L copper;n,n-dimethylcarbamodithioate Chemical compound [Cu+2].CN(C)C([S-])=S.CN(C)C([S-])=S ZOUQIAGHKFLHIA-UHFFFAOYSA-L 0.000 description 1
- BTSJZPQOSLORGE-UHFFFAOYSA-L copper;n,n-dipentylcarbamodithioate Chemical compound [Cu+2].CCCCCN(C([S-])=S)CCCCC.CCCCCN(C([S-])=S)CCCCC BTSJZPQOSLORGE-UHFFFAOYSA-L 0.000 description 1
- UQMKZLGQBFCRSN-UHFFFAOYSA-L copper;n,n-dipropylcarbamodithioate Chemical compound [Cu+2].CCCN(C([S-])=S)CCC.CCCN(C([S-])=S)CCC UQMKZLGQBFCRSN-UHFFFAOYSA-L 0.000 description 1
- QNLDJGYWFHOXOK-UHFFFAOYSA-L copper;n-butyl-n-ethylcarbamodithioate Chemical compound [Cu+2].CCCCN(CC)C([S-])=S.CCCCN(CC)C([S-])=S QNLDJGYWFHOXOK-UHFFFAOYSA-L 0.000 description 1
- WTBRSERGLKIACY-UHFFFAOYSA-L copper;n-butyl-n-hexylcarbamodithioate Chemical compound [Cu+2].CCCCCCN(C([S-])=S)CCCC.CCCCCCN(C([S-])=S)CCCC WTBRSERGLKIACY-UHFFFAOYSA-L 0.000 description 1
- XZNRKCTYUWUQSR-UHFFFAOYSA-L copper;n-butyl-n-methylcarbamodithioate Chemical compound [Cu+2].CCCCN(C)C([S-])=S.CCCCN(C)C([S-])=S XZNRKCTYUWUQSR-UHFFFAOYSA-L 0.000 description 1
- YXGGLBLEYDQHRR-UHFFFAOYSA-L copper;n-butyl-n-pentylcarbamodithioate Chemical compound [Cu+2].CCCCCN(C([S-])=S)CCCC.CCCCCN(C([S-])=S)CCCC YXGGLBLEYDQHRR-UHFFFAOYSA-L 0.000 description 1
- GMGSDIPTNOEOIE-UHFFFAOYSA-L copper;n-butyl-n-phenylcarbamodithioate Chemical compound [Cu+2].CCCCN(C([S-])=S)C1=CC=CC=C1.CCCCN(C([S-])=S)C1=CC=CC=C1 GMGSDIPTNOEOIE-UHFFFAOYSA-L 0.000 description 1
- HOBWWMFINPBQMT-UHFFFAOYSA-L copper;n-butyl-n-propylcarbamodithioate Chemical compound [Cu+2].CCCCN(C([S-])=S)CCC.CCCCN(C([S-])=S)CCC HOBWWMFINPBQMT-UHFFFAOYSA-L 0.000 description 1
- PPGZPMBIGPGTQF-UHFFFAOYSA-L copper;n-ethyl-n-hexylcarbamodithioate Chemical compound [Cu+2].CCCCCCN(CC)C([S-])=S.CCCCCCN(CC)C([S-])=S PPGZPMBIGPGTQF-UHFFFAOYSA-L 0.000 description 1
- RPIHXQMCRSIBBH-UHFFFAOYSA-L copper;n-ethyl-n-methylcarbamodithioate Chemical compound [Cu+2].CCN(C)C([S-])=S.CCN(C)C([S-])=S RPIHXQMCRSIBBH-UHFFFAOYSA-L 0.000 description 1
- CDWYCTVNTQKXGA-UHFFFAOYSA-L copper;n-ethyl-n-pentylcarbamodithioate Chemical compound [Cu+2].CCCCCN(CC)C([S-])=S.CCCCCN(CC)C([S-])=S CDWYCTVNTQKXGA-UHFFFAOYSA-L 0.000 description 1
- HOGZQCHCQNNPNS-UHFFFAOYSA-L copper;n-ethyl-n-phenylcarbamodithioate Chemical compound [Cu+2].CCN(C([S-])=S)C1=CC=CC=C1.CCN(C([S-])=S)C1=CC=CC=C1 HOGZQCHCQNNPNS-UHFFFAOYSA-L 0.000 description 1
- JYIYUJBHEGUHRO-UHFFFAOYSA-L copper;n-ethyl-n-propylcarbamodithioate Chemical compound [Cu+2].CCCN(CC)C([S-])=S.CCCN(CC)C([S-])=S JYIYUJBHEGUHRO-UHFFFAOYSA-L 0.000 description 1
- OFVIMKSVEOVZHG-UHFFFAOYSA-L copper;n-hexyl-n-methylcarbamodithioate Chemical compound [Cu+2].CCCCCCN(C)C([S-])=S.CCCCCCN(C)C([S-])=S OFVIMKSVEOVZHG-UHFFFAOYSA-L 0.000 description 1
- XJWCVMTWXKXGIJ-UHFFFAOYSA-L copper;n-hexyl-n-pentylcarbamodithioate Chemical compound [Cu+2].CCCCCCN(C([S-])=S)CCCCC.CCCCCCN(C([S-])=S)CCCCC XJWCVMTWXKXGIJ-UHFFFAOYSA-L 0.000 description 1
- PZRZDYNNKYFIBO-UHFFFAOYSA-L copper;n-hexyl-n-phenylcarbamodithioate Chemical compound [Cu+2].CCCCCCN(C([S-])=S)C1=CC=CC=C1.CCCCCCN(C([S-])=S)C1=CC=CC=C1 PZRZDYNNKYFIBO-UHFFFAOYSA-L 0.000 description 1
- GDXBPDCQYJYKOO-UHFFFAOYSA-L copper;n-hexyl-n-propylcarbamodithioate Chemical compound [Cu+2].CCCCCCN(C([S-])=S)CCC.CCCCCCN(C([S-])=S)CCC GDXBPDCQYJYKOO-UHFFFAOYSA-L 0.000 description 1
- IMWDPWPXXFUSPE-UHFFFAOYSA-L copper;n-methyl-n-pentylcarbamodithioate Chemical compound [Cu+2].CCCCCN(C)C([S-])=S.CCCCCN(C)C([S-])=S IMWDPWPXXFUSPE-UHFFFAOYSA-L 0.000 description 1
- JATUHITVIFHTDZ-UHFFFAOYSA-L copper;n-methyl-n-phenylcarbamodithioate Chemical compound [Cu+2].[S-]C(=S)N(C)C1=CC=CC=C1.[S-]C(=S)N(C)C1=CC=CC=C1 JATUHITVIFHTDZ-UHFFFAOYSA-L 0.000 description 1
- CYSXAJXJMFDNMS-UHFFFAOYSA-L copper;n-methyl-n-propylcarbamodithioate Chemical compound [Cu+2].CCCN(C)C([S-])=S.CCCN(C)C([S-])=S CYSXAJXJMFDNMS-UHFFFAOYSA-L 0.000 description 1
- AJUQYYZUDMPNEE-UHFFFAOYSA-L copper;n-pentyl-n-propylcarbamodithioate Chemical compound [Cu+2].CCCCCN(C([S-])=S)CCC.CCCCCN(C([S-])=S)CCC AJUQYYZUDMPNEE-UHFFFAOYSA-L 0.000 description 1
- JAUHRSQWPREBLY-UHFFFAOYSA-L copper;n-phenyl-n-propylcarbamodithioate Chemical compound [Cu+2].CCCN(C([S-])=S)C1=CC=CC=C1.CCCN(C([S-])=S)C1=CC=CC=C1 JAUHRSQWPREBLY-UHFFFAOYSA-L 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([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
- 230000001771 impaired effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 150000002696 manganese Chemical class 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
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
- SRWMQSFFRFWREA-UHFFFAOYSA-M zinc formate Chemical compound [Zn+2].[O-]C=O SRWMQSFFRFWREA-UHFFFAOYSA-M 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- MBBWTVUFIXOUBE-UHFFFAOYSA-L zinc;dicarbamodithioate Chemical compound [Zn+2].NC([S-])=S.NC([S-])=S MBBWTVUFIXOUBE-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
- C07C57/04—Acrylic acid; Methacrylic acid
-
- 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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
- C07B63/04—Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21570594 | 1994-09-09 | ||
| PCT/JP1995/001705 WO1996007631A1 (fr) | 1994-09-09 | 1995-08-29 | Procede d'inhibition de la polymerisation d'un compose vinylique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP3544985B2 true JP3544985B2 (ja) | 2004-07-21 |
Family
ID=16676803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50936796A Expired - Lifetime JP3544985B2 (ja) | 1994-09-09 | 1995-08-29 | ビニル化合物の重合防止方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US5886220A (en, 2012) |
| EP (2) | EP0781755A4 (en, 2012) |
| JP (1) | JP3544985B2 (en, 2012) |
| KR (1) | KR100408362B1 (en, 2012) |
| CN (1) | CN1069305C (en, 2012) |
| MY (1) | MY115982A (en, 2012) |
| TW (1) | TW289033B (en, 2012) |
| WO (1) | WO1996007631A1 (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1069305C (zh) * | 1994-09-09 | 2001-08-08 | 出光石油化学株式会社 | 防止乙烯基化合物聚合的方法 |
| FR2753445B1 (fr) * | 1996-09-16 | 1998-10-30 | Atochem Elf Sa | Procede perfectionne de purification de l'acide acrylique |
| GB9819600D0 (en) * | 1998-09-08 | 1998-11-04 | Marks A H & Co Ltd | Chemical compositions |
| AU2002349756A1 (en) * | 2001-12-05 | 2003-06-17 | Mitsubishi Chemical Corporation | Method of purifying (meth)acrylic ester |
| KR101906096B1 (ko) * | 2012-08-24 | 2018-10-08 | 미쯔비시 케미컬 주식회사 | 카복실산 철의 제조 방법 |
| US9781841B2 (en) | 2015-03-27 | 2017-10-03 | Det International Holding Limited | Soldering apparatus with automatic aligning function |
| CN116421594A (zh) * | 2022-01-04 | 2023-07-14 | 中南大学 | 一种nlrp3炎性小体抑制剂及其应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4021310A (en) * | 1972-12-22 | 1977-05-03 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | Method for inhibiting the polymerization of acrylic acid or its esters |
| JPS5761015B2 (en, 2012) * | 1974-01-16 | 1982-12-22 | Nippon Shokubai Kagaku Kogyo Kk | |
| JPS5129328A (en) * | 1974-08-29 | 1976-03-12 | Sumitomo Chemical Co | Aruminiumu mataha aruminiumugokin no hyomenniseiseisaseta yokyokusankahimaku no denkaichakushokuhoho |
| US4532011A (en) * | 1984-03-02 | 1985-07-30 | The Goodyear Tire & Rubber Company | Inhibiting polymerization of vinylaromatic monomers |
| US5128484A (en) * | 1987-12-28 | 1992-07-07 | Sokubai Kagaku Kogyo, Co., Ltd. | Acrylonitrile maleimides solution composition of improved shelf life and method for production thereof |
| GB9000436D0 (en) * | 1990-01-09 | 1990-03-07 | Shell Int Research | Process for shortstopping an emulsion polymerization |
| EP0485169B1 (en) * | 1990-11-09 | 1995-07-19 | Nippon Shokubai Co., Ltd. | Polymerization inhibitor and inhibiting method for vinyl compound |
| CN1031269C (zh) * | 1990-11-09 | 1996-03-13 | 株式会社日本触媒 | 用于乙烯系化合物的聚合抑制方法 |
| JPH0772204B2 (ja) * | 1990-11-09 | 1995-08-02 | 株式会社日本触媒 | ビニル化合物の重合防止剤および重合防止方法 |
| US5130471A (en) * | 1991-09-06 | 1992-07-14 | Heiman John C | Stabilized acrylic monomer compositions |
| US5322960A (en) * | 1993-04-15 | 1994-06-21 | Nippon Shokubai Co., Ltd. | Method for inhibiting polymerization of (meth) acrylic acid and esters thereof |
| CN1069305C (zh) * | 1994-09-09 | 2001-08-08 | 出光石油化学株式会社 | 防止乙烯基化合物聚合的方法 |
-
1995
- 1995-08-29 CN CN95194943A patent/CN1069305C/zh not_active Expired - Lifetime
- 1995-08-29 EP EP95929240A patent/EP0781755A4/en not_active Ceased
- 1995-08-29 KR KR1019970701130A patent/KR100408362B1/ko not_active Expired - Fee Related
- 1995-08-29 WO PCT/JP1995/001705 patent/WO1996007631A1/ja active IP Right Grant
- 1995-08-29 US US08/793,600 patent/US5886220A/en not_active Expired - Lifetime
- 1995-08-29 JP JP50936796A patent/JP3544985B2/ja not_active Expired - Lifetime
- 1995-08-29 EP EP00110689A patent/EP1043303A1/en not_active Withdrawn
- 1995-09-02 TW TW084109193A patent/TW289033B/zh not_active IP Right Cessation
- 1995-09-06 MY MYPI9502643 patent/MY115982A/en unknown
-
1998
- 1998-12-15 US US09/210,885 patent/US6051735A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0781755A4 (en) | 1998-04-29 |
| KR100408362B1 (ko) | 2004-03-24 |
| US6051735A (en) | 2000-04-18 |
| WO1996007631A1 (fr) | 1996-03-14 |
| EP1043303A1 (en) | 2000-10-11 |
| US5886220A (en) | 1999-03-23 |
| TW289033B (en, 2012) | 1996-10-21 |
| CN1069305C (zh) | 2001-08-08 |
| EP0781755A1 (en) | 1997-07-02 |
| MY115982A (en) | 2003-10-31 |
| CN1157606A (zh) | 1997-08-20 |
| KR970705532A (ko) | 1997-10-09 |
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