CN1009650B - 盐催化剂的减活 - Google Patents
盐催化剂的减活Info
- Publication number
- CN1009650B CN1009650B CN87103127A CN87103127A CN1009650B CN 1009650 B CN1009650 B CN 1009650B CN 87103127 A CN87103127 A CN 87103127A CN 87103127 A CN87103127 A CN 87103127A CN 1009650 B CN1009650 B CN 1009650B
- Authority
- CN
- China
- Prior art keywords
- reaction
- epoxy
- catalyzer
- acid
- phosphonium salt
- 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
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 21
- 230000009849 deactivation Effects 0.000 title abstract description 23
- 150000003839 salts Chemical class 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 22
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 14
- -1 hydrocarbyl phosphonium salt Chemical class 0.000 claims abstract description 13
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 11
- 239000003822 epoxy resin Substances 0.000 claims abstract description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims abstract description 6
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229940098779 methanesulfonic acid Drugs 0.000 claims abstract 2
- 239000004593 Epoxy Substances 0.000 claims description 27
- 239000011541 reaction mixture Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 12
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 7
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 150000004714 phosphonium salts Chemical class 0.000 abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract description 5
- 238000001723 curing Methods 0.000 description 22
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- 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 12
- 150000002989 phenols Chemical class 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 229940106691 bisphenol a Drugs 0.000 description 6
- 150000002118 epoxides Chemical class 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 235000013824 polyphenols Nutrition 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 150000008442 polyphenolic compounds Chemical class 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-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
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 2
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- REPWBKQJAMXHFL-UHFFFAOYSA-N phenylphosphane;hydrobromide Chemical class [Br-].[PH3+]C1=CC=CC=C1 REPWBKQJAMXHFL-UHFFFAOYSA-N 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- ZNPSUQQXTRRSBM-UHFFFAOYSA-N 4-n-Pentylphenol Chemical class CCCCCC1=CC=C(O)C=C1 ZNPSUQQXTRRSBM-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000370738 Chlorion Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- HLSMGGKZHOXWIG-UHFFFAOYSA-N OC1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)O.OC1=CC=C(C=C1)CCC Chemical compound OC1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)O.OC1=CC=C(C=C1)CCC HLSMGGKZHOXWIG-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 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
- 235000021050 feed intake Nutrition 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229940006461 iodide ion Drugs 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- 229940100630 metacresol Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- CUXQLKLUPGTTKL-UHFFFAOYSA-M microcosmic salt Chemical compound [NH4+].[Na+].OP([O-])([O-])=O CUXQLKLUPGTTKL-UHFFFAOYSA-M 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 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
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
-
- 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
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/688—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing phosphorus
-
- 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
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)
- Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/858,311 US4692504A (en) | 1986-04-30 | 1986-04-30 | Deactivation of phosphonium salt catalyst |
| US858311 | 1986-04-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN87103127A CN87103127A (zh) | 1987-12-30 |
| CN1009650B true CN1009650B (zh) | 1990-09-19 |
Family
ID=25328000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN87103127A Expired CN1009650B (zh) | 1986-04-30 | 1987-04-28 | 盐催化剂的减活 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4692504A (OSRAM) |
| EP (1) | EP0244015B1 (OSRAM) |
| JP (1) | JPS62262749A (OSRAM) |
| KR (1) | KR870010101A (OSRAM) |
| CN (1) | CN1009650B (OSRAM) |
| AT (1) | ATE78274T1 (OSRAM) |
| AU (1) | AU584796B2 (OSRAM) |
| BR (1) | BR8702060A (OSRAM) |
| CA (1) | CA1309548C (OSRAM) |
| DE (1) | DE3780349T2 (OSRAM) |
| ES (1) | ES2041674T3 (OSRAM) |
| GR (1) | GR3005295T3 (OSRAM) |
| ZA (1) | ZA873012B (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1319446C (zh) * | 2004-09-27 | 2007-06-06 | 深圳市绿微康生物工程有限公司 | 新型生物农药－松刚霉素生产方法 |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4946817A (en) * | 1984-07-17 | 1990-08-07 | The Dow Chemical Company | Latent catalysts for epoxy-containing compounds |
| US5503937A (en) * | 1984-07-17 | 1996-04-02 | The Dow Chemical Company | Curable composition which comprises adducts of heterocyclic compounds |
| US5202051A (en) * | 1987-04-29 | 1993-04-13 | Shell Oil Company | Stabilization of epoxy/nitroparaffin solutions |
| US4933420A (en) * | 1988-09-23 | 1990-06-12 | The Dow Chemical Company | Epoxy resins containing phosphonium catalysts |
| US4939112A (en) * | 1988-10-06 | 1990-07-03 | James River Paper Company, Inc. | Catalyst for synthesis of vesicular phenoxy resins |
| US5310854A (en) * | 1989-08-23 | 1994-05-10 | The Dow Chemical Company | Epoxy resin composition and process therefor |
| US5208317A (en) * | 1990-02-06 | 1993-05-04 | The Dow Chemical Company | Composition comprising epoxy resin and cationic amine phosphonium catalyst |
| US5140079A (en) * | 1990-02-06 | 1992-08-18 | The Dow Chemical Company | Latent, curable, catalyzed mixtures of epoxy-containing and phenolic-hydroxyl-containing compounds containing compounds or complexes formed from contacting organic phosphines or arsines with weak nucleophilic acids |
| US4981926A (en) * | 1990-02-06 | 1991-01-01 | The Dow Chemical Company | Composition of epoxy resin, amino group-containing phosphonium catalyst and curing agent |
| US5169473A (en) * | 1990-05-21 | 1992-12-08 | The Dow Chemical Company | Latent catalysts, epoxy compositions incorporating same, and coating, impregnating and bonding methods employing the compositions |
| US5721323A (en) * | 1990-05-21 | 1998-02-24 | The Dow Chemical Company | Cure inhibited epoxy resin compositions and laminates prepared from the compositions |
| ZA913801B (en) * | 1990-05-21 | 1993-01-27 | Dow Chemical Co | Latent catalysts,cure-inhibited epoxy resin compositions and laminates prepared therefrom |
| US5202407A (en) * | 1992-01-24 | 1993-04-13 | The Dow Chemical Company | Precatalyzed catalyst compositions, process for preparing epoxy resins curable compositions, articles resulting from curing the resultant compositions |
| DE19547786A1 (de) * | 1995-12-20 | 1997-06-26 | Basf Lacke & Farben | Aufbau von modifizierten Epoxidharzen für die kathodische Elektrotauchlackierung mit Katalysator-Desaktivierung und Diolmodifizierung |
| JP2004210672A (ja) * | 2002-12-27 | 2004-07-29 | Nippon Chem Ind Co Ltd | ビスホスホニウム塩化合物及びその製造方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3477990A (en) * | 1967-12-07 | 1969-11-11 | Shell Oil Co | Process for reacting a phenol with an epoxy compound and resulting products |
| US3547885A (en) * | 1968-03-08 | 1970-12-15 | Sun Oil Co | Process for curing polyepoxides with anhydrides and phosphonium halide catalysts therefor |
| DE2416227C3 (de) * | 1974-04-03 | 1980-04-30 | Chemische Werke Huels Ag, 4370 Marl | Verfahren zur Entfernung von Katalysatoren aus flüssigen Reaktionsgemischen |
| US3978027A (en) * | 1975-05-07 | 1976-08-31 | Shell Oil Company | Process for reacting a phenol with an epoxy compound |
| US4410596A (en) * | 1980-12-04 | 1983-10-18 | The Dow Chemical Co. | Process for preparing epoxy resins having improved physical properties when cured |
| US4370465A (en) * | 1980-12-04 | 1983-01-25 | The Dow Chemical Co. | Epoxy resins having improved physical properties when cured |
| US4352918A (en) * | 1980-12-04 | 1982-10-05 | The Dow Chemical Company | Process for preparing epoxy resins having improved physical properties when cured using quaternary phosphonium catalysts |
| US4366295A (en) * | 1981-06-01 | 1982-12-28 | The Dow Chemical Company | Stable precatalyzed epoxy resin compositions |
| US4496709A (en) * | 1982-06-23 | 1985-01-29 | The Dow Chemical Company | Process for preparing epoxy resins employing a phosphonium trifluoroacetate catalyst |
| US4438254A (en) * | 1983-02-28 | 1984-03-20 | The Dow Chemical Company | Process for producing epoxy resins |
| GB8420817D0 (en) * | 1984-08-16 | 1984-09-19 | Dow Chemical Rheinwerk Gmbh | Preparing epoxy resins |
-
1986
- 1986-04-30 US US06/858,311 patent/US4692504A/en not_active Expired - Fee Related
-
1987
- 1987-04-07 CA CA000533994A patent/CA1309548C/en not_active Expired - Fee Related
- 1987-04-15 DE DE8787200731T patent/DE3780349T2/de not_active Expired - Lifetime
- 1987-04-15 ES ES198787200731T patent/ES2041674T3/es not_active Expired - Lifetime
- 1987-04-15 AT AT87200731T patent/ATE78274T1/de active
- 1987-04-15 EP EP87200731A patent/EP0244015B1/en not_active Expired - Lifetime
- 1987-04-28 CN CN87103127A patent/CN1009650B/zh not_active Expired
- 1987-04-28 JP JP62103485A patent/JPS62262749A/ja active Pending
- 1987-04-28 KR KR870004122A patent/KR870010101A/ko not_active Withdrawn
- 1987-04-28 AU AU72149/87A patent/AU584796B2/en not_active Ceased
- 1987-04-28 ZA ZA873012A patent/ZA873012B/xx unknown
- 1987-04-28 BR BR8702060A patent/BR8702060A/pt not_active IP Right Cessation
-
1992
- 1992-07-29 GR GR920401626T patent/GR3005295T3/el unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1319446C (zh) * | 2004-09-27 | 2007-06-06 | 深圳市绿微康生物工程有限公司 | 新型生物农药－松刚霉素生产方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3780349D1 (de) | 1992-08-20 |
| ATE78274T1 (de) | 1992-08-15 |
| CA1309548C (en) | 1992-10-27 |
| AU7214987A (en) | 1987-11-05 |
| ZA873012B (en) | 1987-11-25 |
| EP0244015B1 (en) | 1992-07-15 |
| JPS62262749A (ja) | 1987-11-14 |
| GR3005295T3 (OSRAM) | 1993-05-24 |
| DE3780349T2 (de) | 1992-12-17 |
| BR8702060A (pt) | 1988-02-09 |
| US4692504A (en) | 1987-09-08 |
| KR870010101A (ko) | 1987-11-30 |
| AU584796B2 (en) | 1989-06-01 |
| CN87103127A (zh) | 1987-12-30 |
| EP0244015A2 (en) | 1987-11-04 |
| EP0244015A3 (en) | 1989-02-01 |
| ES2041674T3 (es) | 1993-12-01 |
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| Publication | Publication Date | Title |
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