DE2155431A1 - Verfahren zur Herstellung von cyclischen, dianhydridabgeschlossenen Monomeren - Google Patents
Verfahren zur Herstellung von cyclischen, dianhydridabgeschlossenen MonomerenInfo
- Publication number
- DE2155431A1 DE2155431A1 DE19712155431 DE2155431A DE2155431A1 DE 2155431 A1 DE2155431 A1 DE 2155431A1 DE 19712155431 DE19712155431 DE 19712155431 DE 2155431 A DE2155431 A DE 2155431A DE 2155431 A1 DE2155431 A1 DE 2155431A1
- Authority
- DE
- Germany
- Prior art keywords
- dianhydride
- reaction
- solution
- diimide
- acid
- 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.)
- Pending
Links
- 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 title claims description 15
- 238000000034 method Methods 0.000 title claims description 13
- 239000000178 monomer Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- 125000004122 cyclic group Chemical group 0.000 title claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 150000008064 anhydrides Chemical class 0.000 claims description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 6
- 239000001294 propane Substances 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 4
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- GQANXAAOGTXTHV-UHFFFAOYSA-N 4-(4-chlorobutyl)isoindole-1,3-dione Chemical compound ClCCCCC1=CC=CC2=C1C(=O)NC2=O GQANXAAOGTXTHV-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 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 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 12
- 229910000071 diazene Inorganic materials 0.000 description 12
- -1 sulfone compound Chemical class 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
- 150000003949 imides Chemical class 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000001491 aromatic compounds Chemical class 0.000 description 6
- 230000008030 elimination Effects 0.000 description 6
- 238000003379 elimination reaction Methods 0.000 description 6
- MWZMHSGEQHVWED-UHFFFAOYSA-M sodium;4-chlorophthalate;hydron Chemical compound [Na+].OC(=O)C1=CC=C(Cl)C=C1C([O-])=O MWZMHSGEQHVWED-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 150000003457 sulfones Chemical class 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- 150000007824 aliphatic compounds Chemical class 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- 239000012286 potassium permanganate Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001923 cyclic compounds Chemical class 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 238000007344 nucleophilic reaction Methods 0.000 description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003139 primary aliphatic amines Chemical class 0.000 description 2
- 150000003142 primary aromatic amines Chemical class 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- KUTSHLYTHWTGQB-UHFFFAOYSA-N 1,4-dihydroxyanthracene-9,10-dione;1,5-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C=CC=C2O.O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O KUTSHLYTHWTGQB-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- MWGATWIBSKHFMR-UHFFFAOYSA-N 2-anilinoethanol Chemical compound OCCNC1=CC=CC=C1 MWGATWIBSKHFMR-UHFFFAOYSA-N 0.000 description 1
- OVZMDALKVWTJIF-UHFFFAOYSA-N 2-butyl-5-chloroisoindole-1,3-dione Chemical compound C1=C(Cl)C=C2C(=O)N(CCCC)C(=O)C2=C1 OVZMDALKVWTJIF-UHFFFAOYSA-N 0.000 description 1
- DLKDEVCJRCPTLN-UHFFFAOYSA-N 2-butylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCC)C(=O)C2=C1 DLKDEVCJRCPTLN-UHFFFAOYSA-N 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- LZRPBDKQEKDMJB-UHFFFAOYSA-N 3,4-dihydro-2h-naphthalene-1,1-diol Chemical compound C1=CC=C2C(O)(O)CCCC2=C1 LZRPBDKQEKDMJB-UHFFFAOYSA-N 0.000 description 1
- BKFXSOCDAQACQM-UHFFFAOYSA-N 3-chlorophthalic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1C(O)=O BKFXSOCDAQACQM-UHFFFAOYSA-N 0.000 description 1
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 1
- JJVKWFOGASBDAO-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;sodium Chemical compound [Na].[Na].C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 JJVKWFOGASBDAO-UHFFFAOYSA-N 0.000 description 1
- DVIPPHSQIBKWSA-UHFFFAOYSA-N 4-chlorophthalic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1C(O)=O DVIPPHSQIBKWSA-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- RLXKJHQKSUMZIZ-UHFFFAOYSA-N 5-chloro-2-phenylisoindole-1,3-dione Chemical compound O=C1C2=CC(Cl)=CC=C2C(=O)N1C1=CC=CC=C1 RLXKJHQKSUMZIZ-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
- 239000004642 Polyimide Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- ZIKPHDUOWRIUBF-UHFFFAOYSA-N benzene-1,3-diol;ethane-1,2-diol Chemical compound OCCO.OC1=CC=CC(O)=C1 ZIKPHDUOWRIUBF-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ZLSMCQSGRWNEGX-UHFFFAOYSA-N bis(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1 ZLSMCQSGRWNEGX-UHFFFAOYSA-N 0.000 description 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 1
- 238000009835 boiling Methods 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- WKODVHZBYIBMOC-UHFFFAOYSA-N chembl116175 Chemical compound C1=CC(O)=CC=C1N=NC1=CC=C(O)C=C1 WKODVHZBYIBMOC-UHFFFAOYSA-N 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/14—Monocyclic dicarboxylic acids
- C07C63/15—Monocyclic dicarboxylic acids all carboxyl groups bound to carbon atoms of the six-membered aromatic ring
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/89—Benzo [c] furans; Hydrogenated benzo [c] furans with two oxygen atoms directly attached in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/113,747 US3965125A (en) | 1971-02-08 | 1971-02-08 | Synthesis of certain bis(phthalic anhydrides) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2155431A1 true DE2155431A1 (de) | 1972-08-17 |
Family
ID=22351254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712155431 Pending DE2155431A1 (de) | 1971-02-08 | 1971-11-08 | Verfahren zur Herstellung von cyclischen, dianhydridabgeschlossenen Monomeren |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3965125A (enExample) |
| CA (1) | CA954873A (enExample) |
| DE (1) | DE2155431A1 (enExample) |
| FR (1) | FR2126731A5 (enExample) |
| GB (1) | GB1353962A (enExample) |
| IT (1) | IT940177B (enExample) |
| NL (1) | NL7200956A (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2363785A1 (de) * | 1972-12-29 | 1974-07-04 | Gen Electric | Polyaetherimide |
| DE2412466A1 (de) * | 1973-03-30 | 1974-10-10 | Gen Electric | Aromatische bis(aethermimide) und verfahren zur herstellung von aromatischen bis(aetheranhydriden) |
| US3933862A (en) * | 1974-08-23 | 1976-01-20 | General Electric Company | Aromatic dithio dianhydrides |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4054600A (en) * | 1975-06-27 | 1977-10-18 | General Electric Company | Method for making aromatic bis(ether dicarboxylic acid)s |
| US4273712A (en) * | 1979-05-09 | 1981-06-16 | General Electric Company | Method for making aromatic ether imides |
| US4476309A (en) * | 1983-03-21 | 1984-10-09 | General Electric Company | Method for making aromatic etherimides |
| US4880584A (en) * | 1986-04-25 | 1989-11-14 | Trw, Inc. | Fiber reinforced thermoplastic resin matrix composites |
| US4892896A (en) * | 1988-04-04 | 1990-01-09 | Ethyl Corporation | Processing polyimide precursor compositions |
| US4906760A (en) * | 1988-08-04 | 1990-03-06 | Hoechst Celanese Corp. | Purification of anhydrides |
| US5149761A (en) * | 1988-10-12 | 1992-09-22 | Bayer Aktiengesellschaft | Aromatic ether imides |
| JP2735314B2 (ja) * | 1989-10-06 | 1998-04-02 | 株式会社日立製作所 | 高純度の３，３’，４，４’―ビフェニルテトラカルボン酸又はその酸二無水物の製造方法 |
| US5359092A (en) * | 1993-06-02 | 1994-10-25 | Hay Allan S | Bis-N-aminoimides |
| ES2174156T3 (es) * | 1996-09-05 | 2002-11-01 | Bayer Ag | Perinonas, quinoftalonas y perinona-quinoftalonas puenteadas. |
| EP1183311B1 (en) | 1999-04-07 | 2006-09-27 | Solvay Advanced Polymers, L.L.C. | Poly(biphenyl ether sulfone) resins having improved uv yellowing resistance |
| US6881815B2 (en) * | 2002-09-25 | 2005-04-19 | General Electric Company | Method for the preparation poly(etherimide)s |
| US7820767B2 (en) * | 2006-03-07 | 2010-10-26 | Solvay Advanced Polymers, L.L.C. | Aromatic polyimide composition |
| US8362114B2 (en) * | 2007-02-28 | 2013-01-29 | Solvay Advanced Polymers, L.L.C. | Thermoplastic compositions containing microspheres |
| CN101679741A (zh) * | 2007-04-23 | 2010-03-24 | 索维高级聚合物股份有限公司 | 耐摩擦和磨损的物品 |
| CN104529966A (zh) * | 2015-01-11 | 2015-04-22 | 景炜杰 | 一种双酚a二醚二酐的制备方法 |
| US10829449B2 (en) | 2016-03-29 | 2020-11-10 | Sabic Global Technologies B.V. | Methods of manufacture of bis(ether anhydride)s and polyetherimides |
| WO2020099685A1 (en) | 2018-11-16 | 2020-05-22 | Rhodia Operations | Polymer composites comprising an aliphatic polyamide matrix and sized glass or basalt fibres |
| CN118702656B (zh) * | 2024-08-28 | 2025-06-17 | 安徽秀朗新材料科技有限公司 | 一种绿色环保的聚酰亚胺单体制备工艺 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3431240A (en) * | 1966-04-08 | 1969-03-04 | Minnesota Mining & Mfg | Anhydride-containing linear polyarylsulfones |
-
1971
- 1971-02-08 US US05/113,747 patent/US3965125A/en not_active Expired - Lifetime
- 1971-09-29 CA CA124,008A patent/CA954873A/en not_active Expired
- 1971-10-11 GB GB4728071A patent/GB1353962A/en not_active Expired
- 1971-11-08 DE DE19712155431 patent/DE2155431A1/de active Pending
- 1971-12-16 IT IT83701/71A patent/IT940177B/it active
-
1972
- 1972-01-24 NL NL7200956A patent/NL7200956A/xx unknown
- 1972-02-04 FR FR7203899A patent/FR2126731A5/fr not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2363785A1 (de) * | 1972-12-29 | 1974-07-04 | Gen Electric | Polyaetherimide |
| DE2412466A1 (de) * | 1973-03-30 | 1974-10-10 | Gen Electric | Aromatische bis(aethermimide) und verfahren zur herstellung von aromatischen bis(aetheranhydriden) |
| US3933862A (en) * | 1974-08-23 | 1976-01-20 | General Electric Company | Aromatic dithio dianhydrides |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1353962A (en) | 1974-05-22 |
| IT940177B (it) | 1973-02-10 |
| FR2126731A5 (enExample) | 1972-10-06 |
| NL7200956A (enExample) | 1972-08-10 |
| CA954873A (en) | 1974-09-17 |
| US3965125A (en) | 1976-06-22 |
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