JP5506778B2 - 液状エポキシ樹脂の製造方法 - Google Patents
液状エポキシ樹脂の製造方法Info
- Publication number
- JP5506778B2 JP5506778B2 JP2011501978A JP2011501978A JP5506778B2 JP 5506778 B2 JP5506778 B2 JP 5506778B2 JP 2011501978 A JP2011501978 A JP 2011501978A JP 2011501978 A JP2011501978 A JP 2011501978A JP 5506778 B2 JP5506778 B2 JP 5506778B2
- Authority
- JP
- Japan
- Prior art keywords
- epihalohydrin
- mixture
- epoxy resin
- unreacted
- 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.)
- Active
Links
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 239000000203 mixture Substances 0.000 claims description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 38
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 23
- 150000003944 halohydrins Chemical class 0.000 claims description 23
- 239000007787 solid Substances 0.000 claims description 23
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 19
- 239000007788 liquid Substances 0.000 claims description 19
- 239000003822 epoxy resin Substances 0.000 claims description 18
- 229920000647 polyepoxide Polymers 0.000 claims description 18
- 239000007795 chemical reaction product Substances 0.000 claims description 17
- 239000012074 organic phase Substances 0.000 claims description 13
- 238000001704 evaporation Methods 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- -1 quaternary ammonium halide Chemical class 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 3
- 150000004023 quaternary phosphonium compounds Chemical class 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000010408 film Substances 0.000 claims description 2
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 1
- FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 230000003134 recirculating effect Effects 0.000 claims 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 23
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 13
- 235000013824 polyphenols Nutrition 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 230000008020 evaporation Effects 0.000 description 8
- 150000008442 polyphenolic compounds Chemical class 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000003518 caustics Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000011952 anionic catalyst Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000007033 dehydrochlorination reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 229940051269 1,3-dichloro-2-propanol Drugs 0.000 description 1
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
- ZLRANBHTTCVNCE-UHFFFAOYSA-N 2-phenyl-3-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CN=C1C1=CC=CC=C1 ZLRANBHTTCVNCE-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 108010057081 Merozoite Surface Protein 1 Proteins 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
- FCSHMCFRCYZTRQ-UHFFFAOYSA-N N,N'-diphenylthiourea Chemical compound C=1C=CC=CC=1NC(=S)NC1=CC=CC=C1 FCSHMCFRCYZTRQ-UHFFFAOYSA-N 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- MNOILHPDHOHILI-UHFFFAOYSA-N Tetramethylthiourea Chemical compound CN(C)C(=S)N(C)C MNOILHPDHOHILI-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- JDKXGAYKIYBQQO-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;hydrogen carbonate Chemical compound OC([O-])=O.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JDKXGAYKIYBQQO-UHFFFAOYSA-M 0.000 description 1
- SLAFUPJSGFVWPP-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 SLAFUPJSGFVWPP-UHFFFAOYSA-M 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- CDOAWSMDRRABET-UHFFFAOYSA-M tetrakis(2-hydroxyethyl)azanium;chloride Chemical compound [Cl-].OCC[N+](CCO)(CCO)CCO CDOAWSMDRRABET-UHFFFAOYSA-M 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
- C08G59/063—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with epihalohydrins
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3926908P | 2008-03-25 | 2008-03-25 | |
| US61/039,269 | 2008-03-25 | ||
| PCT/US2009/038089 WO2009120685A2 (en) | 2008-03-25 | 2009-03-24 | Process for manufacturing liquid epoxy resins |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011515566A JP2011515566A (ja) | 2011-05-19 |
| JP2011515566A5 JP2011515566A5 (enExample) | 2012-04-05 |
| JP5506778B2 true JP5506778B2 (ja) | 2014-05-28 |
Family
ID=41066090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011501978A Active JP5506778B2 (ja) | 2008-03-25 | 2009-03-24 | 液状エポキシ樹脂の製造方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8461286B2 (enExample) |
| EP (1) | EP2260067B1 (enExample) |
| JP (1) | JP5506778B2 (enExample) |
| KR (1) | KR101558633B1 (enExample) |
| CN (2) | CN104710597A (enExample) |
| AR (1) | AR071073A1 (enExample) |
| BR (1) | BRPI0907079A2 (enExample) |
| ES (1) | ES2397129T3 (enExample) |
| TW (1) | TWI400262B (enExample) |
| WO (1) | WO2009120685A2 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5399512B2 (ja) * | 2008-12-18 | 2014-01-29 | ダウ グローバル テクノロジーズ エルエルシー | 固体塩をエポキシ樹脂溶液から分離する方法 |
| BR112012014237A2 (pt) * | 2009-12-16 | 2016-06-14 | Dow Global Technologies Llc | processo melhorado para produzir uma resina epóxi líquida |
| EP2760907B1 (en) * | 2011-09-27 | 2017-03-29 | Blue Cube IP LLC | Reciprocating-plate column reactor for epoxidation of epoxy resins |
| KR101985047B1 (ko) * | 2011-12-19 | 2019-05-31 | 블루 큐브 아이피 엘엘씨 | 에폭시 수지 제조 |
| WO2015074684A1 (en) * | 2013-11-20 | 2015-05-28 | Solvay Sa | Process for manufacturing an epoxy resin |
| US11267881B2 (en) | 2017-09-14 | 2022-03-08 | Charles ROSSER | Compositions and methods for treatment of diseases involving CXCL1 function |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB778887A (en) | 1954-07-02 | 1957-07-10 | Daimler Benz Ag | Improvements relating to drive couplings |
| GB788887A (en) | 1955-01-31 | 1958-01-08 | Bataafsche Petroleum | Improvements in or relating to the production of glycidyl ethers of polyhydric phenols |
| US3221032A (en) * | 1960-04-18 | 1965-11-30 | Devoe & Raynolds Co | Continuous process for the preparation of glycidyl polyethers |
| NL161752C (nl) | 1969-06-10 | 1980-08-15 | Shell Int Research | Werkwijze voor het bereiden van laagmoleculaire polyglycidijlethers. |
| CH575405A5 (enExample) | 1973-02-15 | 1976-05-14 | Inventa Ag | |
| JPS55160772A (en) * | 1979-05-29 | 1980-12-13 | Mitsubishi Petrochem Co Ltd | Preparation of glycidyl ether with low saponifiable chlorine content |
| DE2947469A1 (de) | 1979-11-24 | 1981-06-04 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von glycidylaethern ein- oder mehrwertiger phenole |
| JPS5824578A (ja) | 1981-08-05 | 1983-02-14 | Mitsui Petrochem Ind Ltd | グリシジルエ−テルの製造方法 |
| US4390680A (en) * | 1982-03-29 | 1983-06-28 | The Dow Chemical Company | Phenolic hydroxyl-containing compositions and epoxy resins prepared therefrom |
| EP0168138B1 (en) * | 1984-05-14 | 1989-03-15 | Prescant Pty. Limited | Water ring vacuum pump |
| US4624975A (en) * | 1985-03-21 | 1986-11-25 | The Dow Chemical Company | Process for stabilizing the hydrolyzable chloride content in epoxy resins |
| US4582892A (en) * | 1985-05-28 | 1986-04-15 | The Dow Chemical Company | Process for the preparation of epoxy resins |
| DE3850813T2 (de) * | 1987-05-29 | 1994-11-17 | Mitsui Petrochemical Ind | Epoxyverbindungen und diese enthaltende Epoxyharzzusammensetzungen. |
| JP2723943B2 (ja) * | 1988-12-28 | 1998-03-09 | 三井化学株式会社 | 高純度多価フェノールポリグリシジルエーテルの製造方法 |
| US5245057A (en) | 1990-07-20 | 1993-09-14 | The Dow Chemical Company | Horizontal continuous reactor and processes |
| JPH11158248A (ja) | 1997-11-28 | 1999-06-15 | Dainippon Ink & Chem Inc | 高純度エポキシ樹脂の製造方法。 |
-
2009
- 2009-03-24 US US12/933,840 patent/US8461286B2/en active Active
- 2009-03-24 JP JP2011501978A patent/JP5506778B2/ja active Active
- 2009-03-24 BR BRPI0907079-6A patent/BRPI0907079A2/pt not_active IP Right Cessation
- 2009-03-24 WO PCT/US2009/038089 patent/WO2009120685A2/en not_active Ceased
- 2009-03-24 CN CN201510087449.0A patent/CN104710597A/zh active Pending
- 2009-03-24 KR KR1020107023618A patent/KR101558633B1/ko active Active
- 2009-03-24 CN CN2009801191427A patent/CN102046689A/zh active Pending
- 2009-03-24 TW TW098109498A patent/TWI400262B/zh not_active IP Right Cessation
- 2009-03-24 EP EP09725515A patent/EP2260067B1/en not_active Not-in-force
- 2009-03-24 ES ES09725515T patent/ES2397129T3/es active Active
- 2009-03-25 AR ARP090101064A patent/AR071073A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2011515566A (ja) | 2011-05-19 |
| CN102046689A (zh) | 2011-05-04 |
| EP2260067B1 (en) | 2012-10-24 |
| ES2397129T3 (es) | 2013-03-04 |
| TW200948842A (en) | 2009-12-01 |
| US20110028744A1 (en) | 2011-02-03 |
| KR20100139058A (ko) | 2010-12-31 |
| KR101558633B1 (ko) | 2015-10-07 |
| TWI400262B (zh) | 2013-07-01 |
| BRPI0907079A2 (pt) | 2015-07-07 |
| CN104710597A (zh) | 2015-06-17 |
| US8461286B2 (en) | 2013-06-11 |
| WO2009120685A2 (en) | 2009-10-01 |
| WO2009120685A3 (en) | 2009-11-19 |
| AR071073A1 (es) | 2010-05-26 |
| EP2260067A2 (en) | 2010-12-15 |
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