JPS596871B2 - 芳香族ビス（エ−テル酸無水物）の製法 - Google Patents
芳香族ビス（エ−テル酸無水物）の製法Info
- Publication number
- JPS596871B2 JPS596871B2 JP49034777A JP3477774A JPS596871B2 JP S596871 B2 JPS596871 B2 JP S596871B2 JP 49034777 A JP49034777 A JP 49034777A JP 3477774 A JP3477774 A JP 3477774A JP S596871 B2 JPS596871 B2 JP S596871B2
- Authority
- JP
- Japan
- Prior art keywords
- bis
- acid
- ether
- phenyl
- group
- 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
- 125000003118 aryl group Chemical group 0.000 title claims description 27
- -1 ether acid anhydride Chemical class 0.000 title claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 claims description 16
- FZTDWZQGFQIIDA-UHFFFAOYSA-N ethoxyethane;isoindole-1,3-dione Chemical compound CCOCC.C1=CC=C2C(=O)NC(=O)C2=C1 FZTDWZQGFQIIDA-UHFFFAOYSA-N 0.000 claims description 9
- 125000000962 organic group Chemical group 0.000 claims 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 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
- 239000000203 mixture Substances 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000000047 product Substances 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 15
- 238000010992 reflux Methods 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000000921 elemental analysis Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000001294 propane Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000007864 aqueous solution Substances 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
- 239000012043 crude product Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 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 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 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 5
- 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 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 150000000000 tetracarboxylic acids Chemical class 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
- 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
- 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 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000006159 dianhydride group Chemical group 0.000 description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 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
- 239000007787 solid Substances 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 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
- 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
- BLDLRWQLBOJPEB-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfanylphenol Chemical compound OC1=CC=CC=C1SC1=CC=CC=C1O BLDLRWQLBOJPEB-UHFFFAOYSA-N 0.000 description 1
- LSVBBJVITBGNFC-UHFFFAOYSA-N 2-butyl-5-nitroisoindole-1,3-dione Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(CCCC)C(=O)C2=C1 LSVBBJVITBGNFC-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
- 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 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
- 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
- 229930185605 Bisphenol Natural products 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- XMGZWGBXVLJOKE-UHFFFAOYSA-N acetic acid;toluene Chemical compound CC(O)=O.CC1=CC=CC=C1 XMGZWGBXVLJOKE-UHFFFAOYSA-N 0.000 description 1
- YTEMFTFUVKRXNB-UHFFFAOYSA-N acetyl acetate chlorobenzene Chemical compound C(C)(=O)OC(C)=O.ClC1=CC=CC=C1 YTEMFTFUVKRXNB-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- ZRQCPCNEQYFFJV-UHFFFAOYSA-N benzene-1,4-diol;phenol Chemical group OC1=CC=CC=C1.OC1=CC=CC=C1.OC1=CC=C(O)C=C1 ZRQCPCNEQYFFJV-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 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
- 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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005023 xylyl group Chemical group 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US346473A US3879428A (en) | 1973-03-30 | 1973-03-30 | Method for making aromatic bis(ether anhydride)s |
| US346473 | 1989-05-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5024242A JPS5024242A (cg-RX-API-DMAC7.html) | 1975-03-15 |
| JPS596871B2 true JPS596871B2 (ja) | 1984-02-15 |
Family
ID=23359545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP49034777A Expired JPS596871B2 (ja) | 1973-03-30 | 1974-03-29 | 芳香族ビス（エ−テル酸無水物）の製法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3879428A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS596871B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR7402533D0 (cg-RX-API-DMAC7.html) |
| DD (1) | DD112980A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2412466C2 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2228050B1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1469482A (cg-RX-API-DMAC7.html) |
| IT (1) | IT1003928B (cg-RX-API-DMAC7.html) |
| SE (1) | SE419641B (cg-RX-API-DMAC7.html) |
| SU (1) | SU577998A3 (cg-RX-API-DMAC7.html) |
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 |
| US5068353A (en) * | 1986-12-31 | 1991-11-26 | General Electric Company | Synthesis of aromatic bis(ether phthalimide) compounds |
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| US5434240A (en) * | 1994-04-29 | 1995-07-18 | The University Of Liverpool | Poly (imide-ethers) |
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| 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 |
| WO2021113491A1 (en) | 2019-12-03 | 2021-06-10 | Shpp Global Technologies B.V. | Polyimide varnish from high purity bisphenol a dianhydride and articles prepared therefrom |
| WO2021113489A1 (en) | 2019-12-03 | 2021-06-10 | Shpp Global Technologies B.V. | Polyamic acid varnish from high purity bisphenol a dianhydride and articles prepared therefrom |
| CN119487001A (zh) | 2022-07-01 | 2025-02-18 | 高新特殊工程塑料全球技术有限公司 | 3,3’-芳香族双(醚酰亚胺)、其聚醚酰亚胺及其制备方法 |
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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 (cg-RX-API-DMAC7.html) | 1975-05-12 |
| GB1469482A (en) | 1977-04-06 |
| DE2412466A1 (de) | 1974-10-10 |
| FR2228050A1 (cg-RX-API-DMAC7.html) | 1974-11-29 |
| JPS5024242A (cg-RX-API-DMAC7.html) | 1975-03-15 |
| US3879428A (en) | 1975-04-22 |
| FR2228050B1 (cg-RX-API-DMAC7.html) | 1979-04-20 |
| DE2412466C2 (de) | 1986-10-16 |
| 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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