DE2527117C3 - (23-Dihydroxyphenyl)Phosphoniumhydroxid - Inneres Salz - Google Patents
(23-Dihydroxyphenyl)Phosphoniumhydroxid - Inneres SalzInfo
- Publication number
- DE2527117C3 DE2527117C3 DE2527117A DE2527117A DE2527117C3 DE 2527117 C3 DE2527117 C3 DE 2527117C3 DE 2527117 A DE2527117 A DE 2527117A DE 2527117 A DE2527117 A DE 2527117A DE 2527117 C3 DE2527117 C3 DE 2527117C3
- Authority
- DE
- Germany
- Prior art keywords
- dihydroxyphenyl
- phosphonium hydroxide
- reaction
- epoxy
- catalysts
- 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
- 150000003839 salts Chemical class 0.000 title claims description 25
- DJFBJKSMACBYBD-UHFFFAOYSA-N phosphane;hydrate Chemical compound O.P DJFBJKSMACBYBD-UHFFFAOYSA-N 0.000 title claims description 6
- 239000003054 catalyst Substances 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 229920000647 polyepoxide Polymers 0.000 claims description 26
- 239000003822 epoxy resin Substances 0.000 claims description 25
- -1 2,5-dihydroxyphenyl Chemical group 0.000 claims description 19
- 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 claims description 17
- 150000008064 anhydrides Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 150000002989 phenols Chemical class 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000007858 starting material Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 150000002118 epoxides Chemical class 0.000 claims description 9
- 239000004593 Epoxy Substances 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 150000001735 carboxylic acids Chemical class 0.000 claims description 7
- CDSPYXHKFVXXEI-UHFFFAOYSA-N (2,5-dihydroxyphenyl)phosphanium;hydroxide Chemical compound [OH-].OC1=CC=C(O)C([PH3+])=C1 CDSPYXHKFVXXEI-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- IQKKBZVQSKJTKC-UHFFFAOYSA-N (2,5-dihydroxyphenyl)-trioctylphosphanium hydroxide Chemical compound [OH-].C(CCCCCCC)[P+](C1=C(C=CC(=C1)O)O)(CCCCCCCC)CCCCCCCC IQKKBZVQSKJTKC-UHFFFAOYSA-N 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229920006037 cross link polymer Polymers 0.000 claims 2
- 229920000642 polymer Polymers 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- WOUOOYLYAPSNHR-UHFFFAOYSA-N tributyl-(2,5-dihydroxyphenyl)phosphanium;hydroxide Chemical compound [OH-].CCCC[P+](CCCC)(CCCC)C1=CC(O)=CC=C1O WOUOOYLYAPSNHR-UHFFFAOYSA-N 0.000 claims 1
- 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 13
- 239000000047 product Substances 0.000 description 12
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000000576 coating method Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229940005561 1,4-benzoquinone Drugs 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- 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
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical class OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- QFEUITRJBCQRMX-UHFFFAOYSA-N (2,5-dihydroxyphenyl)-triphenylphosphanium;hydroxide Chemical compound [OH-].OC1=CC=C(O)C([P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 QFEUITRJBCQRMX-UHFFFAOYSA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
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- OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical group CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 description 1
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- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
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- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
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- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- NLEPUYHEOSKYJK-UHFFFAOYSA-O tributyl-(2,5-dihydroxyphenyl)phosphanium Chemical compound CCCC[P+](CCCC)(CCCC)C1=CC(O)=CC=C1O NLEPUYHEOSKYJK-UHFFFAOYSA-O 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5442—Aromatic phosphonium compounds (P-C aromatic linkage)
-
- 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
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Epoxy Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48159974A | 1974-06-21 | 1974-06-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2527117A1 DE2527117A1 (de) | 1976-01-02 |
| DE2527117B2 DE2527117B2 (de) | 1977-12-01 |
| DE2527117C3 true DE2527117C3 (de) | 1978-09-28 |
Family
ID=23912608
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2527117A Expired DE2527117C3 (de) | 1974-06-21 | 1975-06-18 | (23-Dihydroxyphenyl)Phosphoniumhydroxid - Inneres Salz |
| DE2559587A Expired DE2559587C3 (de) | 1974-06-21 | 1975-06-18 | Epoxyharzzusammensetzung |
| DE2559611A Expired DE2559611C3 (de) | 1974-06-21 | 1975-06-18 | Verfahren zur Umsetzung von vivinalen Epoxiden mit Phenol und/oder Carbonsäuren oder deren Anhydriden |
| DE2527116A Expired DE2527116C3 (de) | 1974-06-21 | 1975-06-18 | Verfahren zur Herstellung von Epoxypolyaddukten |
| DE2527002A Expired DE2527002C2 (de) | 1974-06-21 | 1975-06-18 | Verfahren zum Umsetzen von Verbindungen mit einer vicinalen Epoxygruppe mit Carbonsäuren oder ihren Anhydriden |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2559587A Expired DE2559587C3 (de) | 1974-06-21 | 1975-06-18 | Epoxyharzzusammensetzung |
| DE2559611A Expired DE2559611C3 (de) | 1974-06-21 | 1975-06-18 | Verfahren zur Umsetzung von vivinalen Epoxiden mit Phenol und/oder Carbonsäuren oder deren Anhydriden |
| DE2527116A Expired DE2527116C3 (de) | 1974-06-21 | 1975-06-18 | Verfahren zur Herstellung von Epoxypolyaddukten |
| DE2527002A Expired DE2527002C2 (de) | 1974-06-21 | 1975-06-18 | Verfahren zum Umsetzen von Verbindungen mit einer vicinalen Epoxygruppe mit Carbonsäuren oder ihren Anhydriden |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4132706A (enExample) |
| JP (3) | JPS5119748A (enExample) |
| BR (3) | BR7503896A (enExample) |
| CA (3) | CA1041696A (enExample) |
| CH (4) | CH618449A5 (enExample) |
| DE (5) | DE2527117C3 (enExample) |
| ES (2) | ES438785A1 (enExample) |
| GB (3) | GB1492868A (enExample) |
| ZA (3) | ZA753391B (enExample) |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5333599Y2 (enExample) * | 1974-01-21 | 1978-08-18 | ||
| US4302574A (en) * | 1979-05-23 | 1981-11-24 | The Dow Chemical Company | Phosphonium phenoxide catalysts for promoting reacting of epoxides with phenols and/or carboxylic acids |
| USRE32951E (en) * | 1980-12-04 | 1989-06-13 | The Dow Chemical Company | Process for preparing epoxy resins having improved physical properties when cured using quaternary phosphonium catalysts |
| US4410596A (en) * | 1980-12-04 | 1983-10-18 | The Dow Chemical Co. | Process for preparing 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 |
| US4370465A (en) * | 1980-12-04 | 1983-01-25 | The Dow Chemical Co. | Epoxy resins having improved physical properties when cured |
| DE3151540A1 (de) * | 1980-12-29 | 1982-08-19 | Ciba-Geigy GmbH, 7867 Wehr | "verwendung von transparenten anhydridhaertbaren epoxidgiessharzen" |
| US4389520A (en) * | 1982-04-05 | 1983-06-21 | Ciba-Geigy Corporation | Advancement catalysts for epoxy resins |
| US4496709A (en) * | 1982-06-23 | 1985-01-29 | The Dow Chemical Company | Process for preparing epoxy resins employing a phosphonium trifluoroacetate catalyst |
| WO1984000171A1 (en) * | 1982-06-23 | 1984-01-19 | Dow Chemical Co | Process for preparing advanced epoxy resins employing a phosphonium trifluoroacetate catalyst |
| US4465722A (en) * | 1982-07-08 | 1984-08-14 | Ciba-Geigy Corporation | Process for the preparation of epoxide resins by the advancement method |
| US4438254A (en) * | 1983-02-28 | 1984-03-20 | The Dow Chemical Company | Process for producing epoxy resins |
| US4540823A (en) * | 1983-07-21 | 1985-09-10 | The Dow Chemical Company | Tetrahydrocarbyl phosphonium salts |
| US4477645A (en) * | 1983-07-21 | 1984-10-16 | The Dow Chemical Company | Immobilized epoxy advancement initiators |
| JPS6053524A (ja) * | 1983-09-01 | 1985-03-27 | Asahi Chem Ind Co Ltd | 難燃性エポキシ樹脂組成物 |
| US4550154A (en) * | 1983-12-27 | 1985-10-29 | Ford Motor Company | Thermosetting coating composition |
| KR900000190B1 (ko) * | 1984-11-16 | 1990-01-23 | 미쓰비시전기 주식회사 | 에폭시수지 조성물 |
| DE3583395D1 (en) * | 1984-12-04 | 1991-08-08 | Dow Chemical Co | Hitzestabiles thermoplastisches harz. |
| JPS61185528A (ja) * | 1985-02-12 | 1986-08-19 | Mitsubishi Electric Corp | エポキシ樹脂組成物 |
| US4634757A (en) * | 1985-07-15 | 1987-01-06 | Shell Oil Company | Fusion product |
| GB8523464D0 (en) * | 1985-09-23 | 1985-10-30 | Ici Plc | Insecticidal alkenes |
| US4732958A (en) * | 1986-12-30 | 1988-03-22 | Shell Oil Company | Epoxy fusion process |
| US5155196A (en) * | 1987-06-01 | 1992-10-13 | The Dow Chemical Company | Polymer resulting from the cure of a preformed chromene-containing mixture |
| JPH078973B2 (ja) * | 1987-11-27 | 1995-02-01 | 三井東圧化学株式会社 | 熱硬化性の溶剤型塗料組成物 |
| US4933420A (en) * | 1988-09-23 | 1990-06-12 | The Dow Chemical Company | Epoxy resins containing phosphonium catalysts |
| JP2547827B2 (ja) * | 1988-10-26 | 1996-10-23 | 昇 丸山 | 給湯システム |
| US4910329A (en) * | 1989-01-11 | 1990-03-20 | Rohm And Haas Company | Process for preparing hydroxyalkyl esters |
| US5310854A (en) * | 1989-08-23 | 1994-05-10 | The Dow Chemical Company | Epoxy resin composition and process therefor |
| US5164472A (en) * | 1990-01-18 | 1992-11-17 | The Dow Chemical Company | Hydroxy-functional polyethers as thermoplastic barrier resins |
| US5208317A (en) * | 1990-02-06 | 1993-05-04 | The Dow Chemical Company | Composition comprising epoxy resin and cationic amine phosphonium catalyst |
| US4981926A (en) * | 1990-02-06 | 1991-01-01 | The Dow Chemical Company | Composition of epoxy resin, amino group-containing phosphonium catalyst and curing agent |
| 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 |
| US20020053734A1 (en) * | 1993-11-16 | 2002-05-09 | Formfactor, Inc. | Probe card assembly and kit, and methods of making same |
| US5414046A (en) * | 1994-06-17 | 1995-05-09 | General Electric Company | Flame retardant polymer compositions comprising thermally stable resins |
| KR100586763B1 (ko) * | 1998-07-02 | 2006-06-08 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 포스포늄보레이트 화합물, 그의 제조방법, 에폭시 수지 조성물용경화 촉매 및 에폭시 수지 조성물 |
| JP4373624B2 (ja) * | 2000-09-04 | 2009-11-25 | 富士フイルム株式会社 | 感熱性組成物、それを用いた平版印刷版原版及びスルホニウム塩化合物 |
| JP4569076B2 (ja) * | 2002-06-05 | 2010-10-27 | 住友ベークライト株式会社 | 硬化促進剤、エポキシ樹脂組成物および半導体装置 |
| JP4128420B2 (ja) * | 2002-09-27 | 2008-07-30 | 住友ベークライト株式会社 | エポキシ樹脂用硬化剤組成物、該硬化剤組成物を用いたエポキシ樹脂組成物および半導体装置 |
| US6855738B2 (en) | 2003-06-06 | 2005-02-15 | Dow Global Technologies Inc. | Nanoporous laminates |
| JP4496778B2 (ja) * | 2004-01-08 | 2010-07-07 | 住友ベークライト株式会社 | 硬化促進剤、エポキシ樹脂組成物および半導体装置 |
| JP5261880B2 (ja) * | 2006-02-27 | 2013-08-14 | 住友ベークライト株式会社 | エポキシ樹脂用硬化促進剤、エポキシ樹脂組成物及び半導体装置 |
| KR20140045954A (ko) | 2011-06-24 | 2014-04-17 | 다우 글로벌 테크놀로지스 엘엘씨 | 열경화성 조성물 및 섬유-보강된 복합체를 제조하는 방법 |
| EP2726531B1 (en) | 2011-06-30 | 2015-07-22 | Dow Global Technologies LLC | Curable epoxy resin systems containing mixtures of amine hardeners and an excess of epoxide groups |
| WO2014062407A2 (en) | 2012-10-19 | 2014-04-24 | Dow Global Technologies Llc | Anhydride-cured epoxy resin systems containing divinylarene dioxides |
| JP6320403B2 (ja) | 2012-11-13 | 2018-05-09 | ダウ グローバル テクノロジーズ エルエルシー | 樹脂移送成形プロセスのためのポリエチレンテトラアミンおよびトリエチレンジアミン触媒を含有するエポキシ樹脂系 |
| EP2920227B1 (en) | 2012-11-13 | 2017-02-08 | Dow Global Technologies LLC | Epoxy resin system containing polyethylene tetraamines for resin transfer molding processes |
| KR102375740B1 (ko) | 2014-02-07 | 2022-03-18 | 다우 글로벌 테크놀로지스 엘엘씨 | 신속하게 경화되는 높은 유리 전이 온도의 에폭시 수지 시스템 |
| JP2017533318A (ja) | 2014-11-11 | 2017-11-09 | ダウ グローバル テクノロジーズ エルエルシー | 速硬化性で高ガラス転移温度のエポキシ樹脂系 |
| JP6978326B2 (ja) | 2015-06-25 | 2021-12-08 | ダウ グローバル テクノロジーズ エルエルシー | 炭素繊維複合材を作製するための新規エポキシ樹脂系 |
| JP6927891B2 (ja) | 2015-07-07 | 2021-09-01 | ダウ グローバル テクノロジーズ エルエルシー | 複合材を作製するための、安定した高ガラス転移温度のエポキシ樹脂系 |
| US20190194525A1 (en) | 2016-06-21 | 2019-06-27 | Dow Global Technologies Llc | Composition for recovering hydrocarbon fluids from a subterranean reservoir |
| WO2017223490A1 (en) | 2016-06-24 | 2017-12-28 | Dow Global Technologies Llc | Method for reducing the permeability of a subterranean formation to aqueous-based fluids |
| CN109563235A (zh) | 2016-06-27 | 2019-04-02 | 陶氏环球技术有限责任公司 | 水溶性α-二醇磺化环氧树脂组合物和其制备方法 |
| US10876032B2 (en) | 2016-06-29 | 2020-12-29 | Dow Global Technologies Llc | Method for recovering hydrocarbon fluids from a subterranean reservoir using alpha-glycol containing sulfonated epoxy resin compound |
| EP3500612B1 (en) | 2016-08-19 | 2025-04-23 | Dow Global Technologies LLC | Epoxy resin compositions containing an internal mold release agent |
| EP3592796B1 (en) | 2017-03-09 | 2021-04-21 | Dow Global Technologies LLC | Stable epoxy/internal mold release agent blends for the manufacture of composite articles |
| JP2020524187A (ja) | 2017-06-20 | 2020-08-13 | ダウ グローバル テクノロジーズ エルエルシー | 繊維強化複合材を製造するためのエポキシ樹脂系 |
| CN108117724A (zh) * | 2017-12-25 | 2018-06-05 | 科化新材料泰州有限公司 | 一种用于半导体封装用的可常温储存型环氧树脂组合物 |
| WO2020005393A1 (en) | 2018-06-26 | 2020-01-02 | Dow Global Technologies Llc | Fibre-reinforced composite and process of making this composite |
| WO2020033036A1 (en) | 2018-08-08 | 2020-02-13 | Dow Global Technologies Llc | Epoxy resin composition |
| WO2020033037A1 (en) | 2018-08-08 | 2020-02-13 | Dow Global Technologies Llc | Epoxy resin composition |
Family Cites Families (2)
| 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 |
| DE2206218A1 (de) | 1972-02-10 | 1973-08-16 | Schering Ag | Verfahren zur herstellung von epoxidharzen |
-
1975
- 1975-05-22 CA CA227,514A patent/CA1041696A/en not_active Expired
- 1975-05-22 CA CA227,512A patent/CA1051031A/en not_active Expired
- 1975-05-22 CA CA227,513A patent/CA1059692A/en not_active Expired
- 1975-05-26 ZA ZA00753391A patent/ZA753391B/xx unknown
- 1975-05-26 ZA ZA00753392A patent/ZA753392B/xx unknown
- 1975-05-26 ZA ZA00753393A patent/ZA753393B/xx unknown
- 1975-06-18 DE DE2527117A patent/DE2527117C3/de not_active Expired
- 1975-06-18 DE DE2559587A patent/DE2559587C3/de not_active Expired
- 1975-06-18 DE DE2559611A patent/DE2559611C3/de not_active Expired
- 1975-06-18 DE DE2527116A patent/DE2527116C3/de not_active Expired
- 1975-06-18 DE DE2527002A patent/DE2527002C2/de not_active Expired
- 1975-06-18 GB GB26032/75A patent/GB1492868A/en not_active Expired
- 1975-06-19 GB GB26193/75A patent/GB1492869A/en not_active Expired
- 1975-06-20 JP JP50074586A patent/JPS5119748A/ja active Pending
- 1975-06-20 CH CH810075A patent/CH618449A5/de not_active IP Right Cessation
- 1975-06-20 JP JP50074587A patent/JPS5113894A/ja active Pending
- 1975-06-20 JP JP50074588A patent/JPS5113895A/ja active Pending
- 1975-06-20 BR BR5007/75D patent/BR7503896A/pt unknown
- 1975-06-20 BR BR5008/75D patent/BR7503897A/pt unknown
- 1975-06-20 CH CH809575A patent/CH617944A5/de not_active IP Right Cessation
- 1975-06-20 BR BR5009/75D patent/BR7503898A/pt unknown
- 1975-06-20 CH CH809675A patent/CH618198A5/de not_active IP Right Cessation
- 1975-06-20 GB GB2634875A patent/GB1464240A/en not_active Expired
- 1975-06-21 ES ES438785A patent/ES438785A1/es not_active Expired
- 1975-06-21 ES ES438786A patent/ES438786A1/es not_active Expired
-
1976
- 1976-04-05 US US05/674,019 patent/US4132706A/en not_active Expired - Lifetime
-
1979
- 1979-11-08 CH CH1002179A patent/CH621564A5/de not_active IP Right Cessation
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