DE2412466C2 - Verfahren zur Herstellung von aromatischen Bis-ätheranhydriden - Google Patents
Verfahren zur Herstellung von aromatischen Bis-ätheranhydridenInfo
- Publication number
- DE2412466C2 DE2412466C2 DE2412466A DE2412466A DE2412466C2 DE 2412466 C2 DE2412466 C2 DE 2412466C2 DE 2412466 A DE2412466 A DE 2412466A DE 2412466 A DE2412466 A DE 2412466A DE 2412466 C2 DE2412466 C2 DE 2412466C2
- Authority
- DE
- Germany
- Prior art keywords
- bis
- phenyl
- product
- mixture
- formula
- 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
- 238000000034 method Methods 0.000 title claims description 14
- 125000003118 aryl group Chemical group 0.000 title claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 9
- BONIIQYTWOPUQI-UHFFFAOYSA-N 4-nitroisoindole-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC2=C1C(=O)NC2=O BONIIQYTWOPUQI-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 21
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- -1 tetracarboxylic acid salt Chemical class 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 10
- 239000001294 propane Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 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 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical class C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 230000020477 pH reduction Effects 0.000 description 4
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- KHDSXXRHWXXXBY-UHFFFAOYSA-N 3-[4-(2,3-dicarboxyphenoxy)phenoxy]phthalic acid Chemical compound OC(=O)C1=CC=CC(OC=2C=CC(OC=3C(=C(C(O)=O)C=CC=3)C(O)=O)=CC=2)=C1C(O)=O KHDSXXRHWXXXBY-UHFFFAOYSA-N 0.000 description 3
- OMOHDUGKQSTKSR-UHFFFAOYSA-N 4-nitro-2-phenylisoindole-1,3-dione Chemical compound O=C1C=2C([N+](=O)[O-])=CC=CC=2C(=O)N1C1=CC=CC=C1 OMOHDUGKQSTKSR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229940106691 bisphenol a Drugs 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 125000006159 dianhydride group Chemical group 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000012454 non-polar solvent Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LVLNPXCISNPHLE-UHFFFAOYSA-N 2-[(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1CC1=CC=CC=C1O LVLNPXCISNPHLE-UHFFFAOYSA-N 0.000 description 2
- MFUPLJQNEXUUDW-UHFFFAOYSA-N 2-phenylisoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1=CC=CC=C1 MFUPLJQNEXUUDW-UHFFFAOYSA-N 0.000 description 2
- XZWYIEAOALEANP-UHFFFAOYSA-N 3-[4-[2-[4-(2,3-dicarboxyphenoxy)phenyl]propan-2-yl]phenoxy]phthalic acid Chemical compound C=1C=C(OC=2C(=C(C(O)=O)C=CC=2)C(O)=O)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=CC(C(O)=O)=C1C(O)=O XZWYIEAOALEANP-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- FZTDWZQGFQIIDA-UHFFFAOYSA-N ethoxyethane;isoindole-1,3-dione Chemical compound CCOCC.C1=CC=C2C(=O)NC(=O)C2=C1 FZTDWZQGFQIIDA-UHFFFAOYSA-N 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 2
- HUYKZYIAFUBPAQ-UHFFFAOYSA-N (2-hydroxyphenyl)-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1O HUYKZYIAFUBPAQ-UHFFFAOYSA-N 0.000 description 1
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- MQCPOLNSJCWPGT-UHFFFAOYSA-N 2,2'-Bisphenol F Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1O MQCPOLNSJCWPGT-UHFFFAOYSA-N 0.000 description 1
- MQXNNWDXHFBFEB-UHFFFAOYSA-N 2,2-bis(2-hydroxyphenyl)propane Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1O MQXNNWDXHFBFEB-UHFFFAOYSA-N 0.000 description 1
- FWIZOFDVGZCRTB-UHFFFAOYSA-N 2-methyl-4-nitroisoindole-1,3-dione Chemical compound C1=CC([N+]([O-])=O)=C2C(=O)N(C)C(=O)C2=C1 FWIZOFDVGZCRTB-UHFFFAOYSA-N 0.000 description 1
- RKSBPFMNOJWYSB-UHFFFAOYSA-N 3,3-Bis(4-hydroxyphenyl)pentane Chemical compound C=1C=C(O)C=CC=1C(CC)(CC)C1=CC=C(O)C=C1 RKSBPFMNOJWYSB-UHFFFAOYSA-N 0.000 description 1
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-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
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
- RQCACQIALULDSK-UHFFFAOYSA-N 4-(4-hydroxyphenyl)sulfinylphenol Chemical compound C1=CC(O)=CC=C1S(=O)C1=CC=C(O)C=C1 RQCACQIALULDSK-UHFFFAOYSA-N 0.000 description 1
- WCUDAIJOADOKAW-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)pentan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)(CCC)C1=CC=C(O)C=C1 WCUDAIJOADOKAW-UHFFFAOYSA-N 0.000 description 1
- KJLPSBMDOIVXSN-UHFFFAOYSA-N 4-[4-[2-[4-(3,4-dicarboxyphenoxy)phenyl]propan-2-yl]phenoxy]phthalic acid Chemical compound C=1C=C(OC=2C=C(C(C(O)=O)=CC=2)C(O)=O)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 KJLPSBMDOIVXSN-UHFFFAOYSA-N 0.000 description 1
- ROFZMKDROVBLNY-UHFFFAOYSA-N 4-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC2=C1C(=O)OC2=O ROFZMKDROVBLNY-UHFFFAOYSA-N 0.000 description 1
- BGJNRQSGJHVURK-UHFFFAOYSA-N 5-chloroisoindole-1,3-dione Chemical compound ClC1=CC=C2C(=O)NC(=O)C2=C1 BGJNRQSGJHVURK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 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
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US346473A US3879428A (en) | 1973-03-30 | 1973-03-30 | Method for making aromatic bis(ether anhydride)s |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2412466A1 DE2412466A1 (de) | 1974-10-10 |
| DE2412466C2 true DE2412466C2 (de) | 1986-10-16 |
Family
ID=23359545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2412466A Expired DE2412466C2 (de) | 1973-03-30 | 1974-03-15 | Verfahren zur Herstellung von aromatischen Bis-ätheranhydriden |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3879428A (enExample) |
| JP (1) | JPS596871B2 (enExample) |
| BR (1) | BR7402533D0 (enExample) |
| DD (1) | DD112980A5 (enExample) |
| DE (1) | DE2412466C2 (enExample) |
| FR (1) | FR2228050B1 (enExample) |
| GB (1) | GB1469482A (enExample) |
| IT (1) | IT1003928B (enExample) |
| SE (1) | SE419641B (enExample) |
| SU (1) | SU577998A3 (enExample) |
Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3944583A (en) * | 1975-02-27 | 1976-03-16 | General Electric Company | Bis-phenoxyphthalic acid anhydrides |
| US3956322A (en) * | 1975-03-14 | 1976-05-11 | General Electric Company | Dianhydrides of bis-(orthodicarboxyphenyloxyphenyl)acetylene and bis-(ortho-dicarboxyphenyloxyphenyl)2,2-dichloroethylene |
| US4054600A (en) * | 1975-06-27 | 1977-10-18 | General Electric Company | Method for making aromatic bis(ether dicarboxylic acid)s |
| US4020069A (en) * | 1975-07-25 | 1977-04-26 | General Electric Company | Preparation of aromatic tetracarboxylic acids |
| US4005134A (en) * | 1975-09-11 | 1977-01-25 | General Electric Company | Method for making aromatic bis(ether dicarboxylic acid) |
| US4048190A (en) * | 1976-02-17 | 1977-09-13 | General Electric Company | Preparation of bisphenol-A bisimides |
| US4017511A (en) * | 1976-03-24 | 1977-04-12 | General Electric Company | Preparation of aromatic bisimides |
| US3992407A (en) * | 1976-04-14 | 1976-11-16 | General Electric Company | Preparation of aromatic bisimides |
| US4054577A (en) * | 1976-05-06 | 1977-10-18 | General Electric Company | Preparation of aromatic bisimides |
| US4196277A (en) * | 1976-07-19 | 1980-04-01 | Trw Inc. | Perfluoroisopropylidene dianhydride and polyimides prepared therefrom |
| US4217281A (en) * | 1976-10-04 | 1980-08-12 | General Electric Company | Imide carbonyl compounds and method for making |
| US4116980A (en) * | 1976-10-04 | 1978-09-26 | General Electric Company | Method for making aromatic bis (ether phthalic acid) or aromatic bis (ether anhydride)s |
| US4273712A (en) * | 1979-05-09 | 1981-06-16 | General Electric Company | Method for making aromatic ether imides |
| GB2096141B (en) * | 1981-04-03 | 1985-04-24 | Gen Electric | Method for making aromatic bis(ether phthalic acid) or aromatic bis(ether anhydride) |
| US4329292A (en) * | 1981-04-16 | 1982-05-11 | General Electric Company | Continuous method for making aromatic bis(ether phthalic acid) or aromatic bis(ether anhydride) |
| US4340545A (en) * | 1981-04-13 | 1982-07-20 | General Electric Company | Method for making aromatic bis(ether anhydrides) |
| US5512676A (en) * | 1987-09-03 | 1996-04-30 | The Boeing Company | Extended amideimide hub for multidimensional oligomers |
| US5693741A (en) * | 1988-03-15 | 1997-12-02 | The Boeing Company | Liquid molding compounds |
| US5969079A (en) * | 1985-09-05 | 1999-10-19 | The Boeing Company | Oligomers with multiple chemically functional end caps |
| US5506060A (en) * | 1981-11-13 | 1996-04-09 | The Boeing Company | Method for making multidimensional ether or ester oligomers |
| US5210213A (en) * | 1983-06-17 | 1993-05-11 | The Boeing Company | Dimensional, crosslinkable oligomers |
| US5516876A (en) * | 1983-09-27 | 1996-05-14 | The Boeing Company | Polyimide oligomers and blends |
| US5705598A (en) | 1985-04-23 | 1998-01-06 | The Boeing Company | Polyester sulfone oligomers and blends |
| US4476309A (en) * | 1983-03-21 | 1984-10-09 | General Electric Company | Method for making aromatic etherimides |
| US4623732A (en) * | 1983-11-18 | 1986-11-18 | General Electric Company | Process for the preparation of N-alkylphthalimide and copolymer derived therefrom |
| EP0184595A1 (en) * | 1984-12-14 | 1986-06-18 | General Electric Company | Process for the synthesis of N-alkylphthalimide |
| US4571425A (en) * | 1985-02-14 | 1986-02-18 | General Electric Company | Method for making aromatic bis(ether anhydride) |
| US5618907A (en) * | 1985-04-23 | 1997-04-08 | The Boeing Company | Thallium catalyzed multidimensional ester oligomers |
| US5610317A (en) * | 1985-09-05 | 1997-03-11 | The Boeing Company | Multiple chemically functional end cap monomers |
| JPH0655710B2 (ja) * | 1985-12-16 | 1994-07-27 | 東燃株式会社 | スルホニル基を有する芳香族化合物及びその製造法 |
| US4757149A (en) * | 1986-12-31 | 1988-07-12 | General Electric Company | Synthesis of bis(N-substituted phthalimide)ethers |
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| US5262516A (en) * | 1991-11-26 | 1993-11-16 | General Electric Company | Method for preparing polyetherimide-polyamide copolymers |
| US5359084A (en) * | 1993-02-18 | 1994-10-25 | General Electric Company | Method of preparing aromatic ether bisimides |
| US5434240A (en) * | 1994-04-29 | 1995-07-18 | The University Of Liverpool | Poly (imide-ethers) |
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| TW399043B (en) * | 1994-05-27 | 2000-07-21 | Gen Electric | Process for preparing bis (ether anhydrides) using alkylamine derived bisimides having low melting temperatures |
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| US7115785B2 (en) * | 2003-08-25 | 2006-10-03 | General Electric Company | Method for making salts hydroxy-substituted hydrocarbons |
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| WO2017172593A1 (en) * | 2016-03-29 | 2017-10-05 | Sabic Global Technologies B.V. | Methods of manufacture of bis(ether anhydride)s and polyetherimides |
| CN106279085B (zh) * | 2016-08-17 | 2018-07-10 | 万华化学集团股份有限公司 | 一种混合异构双醚四甲酸二酐的制备方法 |
| CN107987007B (zh) * | 2017-11-21 | 2020-07-24 | 万华化学集团股份有限公司 | N-烃基-n’-烃基双醚型双邻苯二甲酰亚胺的制备方法 |
| US12258448B2 (en) | 2019-01-31 | 2025-03-25 | Shpp Global Technologies B.V. | Method of making a biphenol dianhydride composition, method for purification of a biphenol dianhydride composition, and poly (etherimides) derived from the biphenol dianhydride |
| CN113330003B (zh) | 2019-01-31 | 2025-07-01 | 高新特殊工程塑料全球技术有限公司 | 制备联苯酚二酐组合物的方法、纯化联苯酚二酐的方法以及衍生自联苯酚二酐的聚(醚酰亚胺) |
| EP3917917A1 (en) | 2019-01-31 | 2021-12-08 | SHPP Global Technologies B.V. | Method for purification of a bisphenol a dianhydride composition, bisphenol a dianhydride composition, poly(etherimide) derived from the bisphenol a dianhydride composition, and articles prepared therefrom |
| EP3917905A1 (en) | 2019-01-31 | 2021-12-08 | SHPP Global Technologies B.V. | Method for purification of a biphenol tetraacid composition and a biphenol tetraacid composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3787475A (en) * | 1971-01-20 | 1974-01-22 | Gen Electric | Process for making aryloxy derivatives of aromatic diesters and dinitriles |
| US3965125A (en) * | 1971-02-08 | 1976-06-22 | Trw Inc. | Synthesis of certain bis(phthalic anhydrides) |
| US3734926A (en) * | 1971-10-04 | 1973-05-22 | Ciba Geigy Corp | Benzophenone-3,4,3{40 ,4-tetracarboxylic acid diimides of 3,5-dialkyl-4-hydroxyphenylsubstituted amines |
| US3746721A (en) * | 1971-10-04 | 1973-07-17 | Ciba Geigy Corp | Aromatic diimides of 3,5-dialkyl-4-hydroxyphenylsubstituted amines |
| DE2261715A1 (de) * | 1972-12-16 | 1974-06-20 | Gen Electric | Polyaetherimide und verfahren zu deren herstellung |
| DE2261714A1 (de) * | 1972-12-16 | 1974-06-20 | Gen Electric | Bis(nitrophthalimide) |
-
1973
- 1973-03-30 US US346473A patent/US3879428A/en not_active Expired - Lifetime
-
1974
- 1974-03-15 DE DE2412466A patent/DE2412466C2/de not_active Expired
- 1974-03-22 GB GB1286774A patent/GB1469482A/en not_active Expired
- 1974-03-26 FR FR7410289A patent/FR2228050B1/fr not_active Expired
- 1974-03-27 IT IT49728/74A patent/IT1003928B/it active
- 1974-03-28 DD DD177527A patent/DD112980A5/xx unknown
- 1974-03-29 BR BR2533/74A patent/BR7402533D0/pt unknown
- 1974-03-29 SE SE7404314A patent/SE419641B/xx not_active IP Right Cessation
- 1974-03-29 SU SU7402018016A patent/SU577998A3/ru active
- 1974-03-29 JP JP49034777A patent/JPS596871B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DD112980A5 (enExample) | 1975-05-12 |
| GB1469482A (en) | 1977-04-06 |
| JPS596871B2 (ja) | 1984-02-15 |
| DE2412466A1 (de) | 1974-10-10 |
| FR2228050A1 (enExample) | 1974-11-29 |
| JPS5024242A (enExample) | 1975-03-15 |
| US3879428A (en) | 1975-04-22 |
| FR2228050B1 (enExample) | 1979-04-20 |
| BR7402533D0 (pt) | 1974-12-03 |
| AU6738874A (en) | 1975-10-02 |
| SU577998A3 (ru) | 1977-10-25 |
| IT1003928B (it) | 1976-06-10 |
| SE419641B (sv) | 1981-08-17 |
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