JPS59500918A - ホスホニウムトリフルオロアセテ−ト触媒を使用するエポキシ樹脂の分子量を増大する方法 - Google Patents
ホスホニウムトリフルオロアセテ−ト触媒を使用するエポキシ樹脂の分子量を増大する方法Info
- Publication number
- JPS59500918A JPS59500918A JP58502360A JP50236083A JPS59500918A JP S59500918 A JPS59500918 A JP S59500918A JP 58502360 A JP58502360 A JP 58502360A JP 50236083 A JP50236083 A JP 50236083A JP S59500918 A JPS59500918 A JP S59500918A
- Authority
- JP
- Japan
- Prior art keywords
- phosphonium
- catalyst
- molecular weight
- epoxy resins
- phenol
- 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.)
- Granted
Links
- 239000003054 catalyst Substances 0.000 title claims description 22
- 239000003822 epoxy resin Substances 0.000 title claims description 16
- 229920000647 polyepoxide Polymers 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 15
- 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 title claims description 8
- OCPJZGYXJQLRCO-UHFFFAOYSA-N phosphanyl 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)OP OCPJZGYXJQLRCO-UHFFFAOYSA-N 0.000 title claims description 4
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 22
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 14
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
- -1 thiophenol compound Chemical class 0.000 claims description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical group OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims 2
- 238000011065 in-situ storage Methods 0.000 claims 2
- 150000002823 nitrates Chemical class 0.000 claims 2
- RUALOJPMDIKFQU-UHFFFAOYSA-N 2-(oxiran-2-ylmethyl)phenol Chemical compound OC1=CC=CC=C1CC1OC1 RUALOJPMDIKFQU-UHFFFAOYSA-N 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- HZZUMXSLPJFMCB-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;acetate Chemical compound CC([O-])=O.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 HZZUMXSLPJFMCB-UHFFFAOYSA-M 0.000 claims 1
- 150000002826 nitrites Chemical class 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 description 17
- 125000003118 aryl group Chemical group 0.000 description 7
- 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 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000004714 phosphonium salts Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000002357 guanidines Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 description 1
- ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BEYRAKAVBGRTOU-UHFFFAOYSA-N C1(CC=CC=C1)O.C1(=CC=CC=C1)O Chemical compound C1(CC=CC=C1)O.C1(=CC=CC=C1)O BEYRAKAVBGRTOU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 241000750631 Takifugu chinensis Species 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 235000021028 berry Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000000460 chlorine Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-O ethylaminium Chemical compound CC[NH3+] QUSNBJAOOMFDIB-UHFFFAOYSA-O 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- FJDLJSWDGIJLDC-UHFFFAOYSA-N sulfane;2,2,2-trifluoroacetic acid Chemical compound [SH3+].[O-]C(=O)C(F)(F)F FJDLJSWDGIJLDC-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US391094 | 1982-06-23 | ||
| PCT/US1983/000942 WO1984000171A1 (en) | 1982-06-23 | 1983-06-17 | Process for preparing advanced epoxy resins employing a phosphonium trifluoroacetate catalyst |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59500918A true JPS59500918A (ja) | 1984-05-24 |
| JPS6215571B2 JPS6215571B2 (enrdf_load_stackoverflow) | 1987-04-08 |
Family
ID=22175283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58502360A Granted JPS59500918A (ja) | 1982-06-23 | 1983-06-17 | ホスホニウムトリフルオロアセテ−ト触媒を使用するエポキシ樹脂の分子量を増大する方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59500918A (enrdf_load_stackoverflow) |
-
1983
- 1983-06-17 JP JP58502360A patent/JPS59500918A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6215571B2 (enrdf_load_stackoverflow) | 1987-04-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3904311B2 (ja) | エポキシ樹脂用硬化剤・硬化促進剤及びエポキシ樹脂組成物 | |
| US4775734A (en) | Non-nucleophilic acid salts of amines as cure accelerators | |
| DE69732651T2 (de) | Epoxidharzhärter,härtungsbeschleuniger und epoxidharzzusammensetzung | |
| US2772248A (en) | Water-soluble epoxy-amine resins | |
| US5439863A (en) | Neutral metal complex salts | |
| JPH0126624B2 (enrdf_load_stackoverflow) | ||
| JP3269126B2 (ja) | エポキシ樹脂用硬化剤及びエポキシ樹脂用硬化促進剤 | |
| EP0065573A1 (en) | METHOD FOR INCREASING THE MOLECULAR WEIGHT OF EPOXID RESINS AND PROCESS FOR THE PREPARATION OF RESIN IMPREGNATED SUBSTRATES. | |
| US3635869A (en) | Catalysis of epoxy resin/carboxylic acid systems with trivalent chromium iii tricarboxylate salts | |
| US3412046A (en) | Catalyzed polyepoxide-anhydride resin systems | |
| JPS6144919A (ja) | ポリエポキシド、アミンおよびスルホニウム塩からなる硬化性組成物 | |
| US4496709A (en) | Process for preparing epoxy resins employing a phosphonium trifluoroacetate catalyst | |
| KR900006913B1 (ko) | 에폭시 수지의 작용성을 증가시키는 방법 | |
| JP3147294B2 (ja) | エポキシ樹脂の周囲温度および周囲温度以下の温度での硬化用速硬化アミン類 | |
| US4404335A (en) | Hydrolyzing epoxy resins in absence of solvent and in presence of oxalic acid and a phosphonium compound | |
| JPH0581584B2 (enrdf_load_stackoverflow) | ||
| JPH03177418A (ja) | 一成分系加熱硬化性エポキシ樹脂組成物 | |
| JPS59500918A (ja) | ホスホニウムトリフルオロアセテ−ト触媒を使用するエポキシ樹脂の分子量を増大する方法 | |
| Wright et al. | Epoxy structural adhesives | |
| JPS604524A (ja) | エポキシ樹脂用潜在性硬化剤 | |
| JPS62502621A (ja) | 調節された転化率のエポキシ樹脂及びそれらの製法 | |
| EP0111562A1 (en) | Process for preparing advanced epoxy resins employing a phosphonium trifluoroacetate catalyst | |
| US3014009A (en) | Carbohydrazide curing agent for epoxide type resins | |
| US4256868A (en) | Epoxy resins containing chemically bonded metal atoms | |
| KR910006331B1 (ko) | 포스포늄 트리플루오로아세테이트 촉매를 사용한 에폭시수지의 제조방법 |