DE2009739A1 - Aromatische Polyimide mit erhöhter Löslichkeit - Google Patents
Aromatische Polyimide mit erhöhter LöslichkeitInfo
- Publication number
- DE2009739A1 DE2009739A1 DE19702009739 DE2009739A DE2009739A1 DE 2009739 A1 DE2009739 A1 DE 2009739A1 DE 19702009739 DE19702009739 DE 19702009739 DE 2009739 A DE2009739 A DE 2009739A DE 2009739 A1 DE2009739 A1 DE 2009739A1
- Authority
- DE
- Germany
- Prior art keywords
- aromatic
- polyimides
- general formula
- cyclization
- mol
- 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
- 229920001721 polyimide Polymers 0.000 title claims description 42
- 239000004642 Polyimide Substances 0.000 title claims description 30
- 125000003118 aryl group Chemical group 0.000 title claims description 16
- 150000004985 diamines Chemical class 0.000 claims description 15
- -1 threads Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 9
- 150000004984 aromatic diamines Chemical class 0.000 claims description 7
- 238000007363 ring formation reaction Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000011888 foil Substances 0.000 claims description 6
- 239000003495 polar organic solvent Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000004952 Polyamide Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229920002647 polyamide Polymers 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000007493 shaping process Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 150000003951 lactams Chemical class 0.000 claims 1
- 238000007669 thermal treatment Methods 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000000137 annealing Methods 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-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
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005496 tempering Methods 0.000 description 2
- PLYHMRQAXIKUIV-UHFFFAOYSA-N 3,3-bis(4-aminophenyl)-2-benzofuran-1-one Chemical compound C1=CC(N)=CC=C1C1(C=2C=CC(N)=CC=2)C2=CC=CC=C2C(=O)O1 PLYHMRQAXIKUIV-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- YWFPGFJLYRKYJZ-UHFFFAOYSA-N 9,9-bis(4-hydroxyphenyl)fluorene Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YWFPGFJLYRKYJZ-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N anhydrous dimethyl-acetamide Natural products CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000002585 base Substances 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
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920005575 poly(amic acid) Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000002699 waste material Substances 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
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
- C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702009739 DE2009739A1 (de) | 1970-03-03 | 1970-03-03 | Aromatische Polyimide mit erhöhter Löslichkeit |
| CA104,843A CA943296A (en) | 1970-03-03 | 1971-02-09 | Aromatic polyimides with increased solubility |
| US00118960A US3758434A (en) | 1970-03-03 | 1971-02-25 | Aromatic polyimides with increased solubility |
| NL7102765A NL7102765A (enExample) | 1970-03-03 | 1971-03-02 | |
| FR7107354A FR2081668B1 (enExample) | 1970-03-03 | 1971-03-03 | |
| BE763723A BE763723A (fr) | 1970-03-03 | 1971-03-03 | Polyimides aromatiques a solubilite plus grande |
| GB2233671A GB1346787A (en) | 1970-03-03 | 1971-04-19 | Aromatic polyamides and a method for the preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702009739 DE2009739A1 (de) | 1970-03-03 | 1970-03-03 | Aromatische Polyimide mit erhöhter Löslichkeit |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2009739A1 true DE2009739A1 (de) | 1971-09-30 |
Family
ID=5763814
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702009739 Pending DE2009739A1 (de) | 1970-03-03 | 1970-03-03 | Aromatische Polyimide mit erhöhter Löslichkeit |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3758434A (enExample) |
| BE (1) | BE763723A (enExample) |
| CA (1) | CA943296A (enExample) |
| DE (1) | DE2009739A1 (enExample) |
| FR (1) | FR2081668B1 (enExample) |
| GB (1) | GB1346787A (enExample) |
| NL (1) | NL7102765A (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3856752A (en) * | 1973-10-01 | 1974-12-24 | Ciba Geigy Corp | Soluble polyimides derived from phenylindane diamines and dianhydrides |
| CH621768A5 (enExample) * | 1976-06-15 | 1981-02-27 | Ciba Geigy Ag | |
| US4196144A (en) * | 1976-06-15 | 1980-04-01 | Ciba-Geigy Corporation | Aromatic diamines and their use as polycondensation components for the manufacture of polyamide, polyamide-imide and polyimide polymers |
| DE3407201A1 (de) * | 1984-02-28 | 1985-08-29 | Bayer Ag, 5090 Leverkusen | Verfahren zur phenolfreien herstellung von aliphatisch-aromatischen polyamidimiden |
| US4935490A (en) * | 1988-04-13 | 1990-06-19 | E. I. Dupont De Nemours And Company | Highly soluble aromatic polyimides |
| US4851505A (en) * | 1988-04-13 | 1989-07-25 | E. I. Du Pont De Nemours And Company | Highly soluble aromatic polyimides |
| EP0875906B1 (en) * | 1997-04-30 | 2004-04-07 | JSR Corporation | Electronic part and process for manufacturing the same |
| US6392004B1 (en) | 2000-08-21 | 2002-05-21 | 3M Innovative Properties Company | Polyimides for high-frequency applications |
| US6417321B1 (en) | 2000-08-21 | 2002-07-09 | 3M Innovative Properties Company | Cured fluorenyl polyimides |
-
1970
- 1970-03-03 DE DE19702009739 patent/DE2009739A1/de active Pending
-
1971
- 1971-02-09 CA CA104,843A patent/CA943296A/en not_active Expired
- 1971-02-25 US US00118960A patent/US3758434A/en not_active Expired - Lifetime
- 1971-03-02 NL NL7102765A patent/NL7102765A/xx unknown
- 1971-03-03 FR FR7107354A patent/FR2081668B1/fr not_active Expired
- 1971-03-03 BE BE763723A patent/BE763723A/xx unknown
- 1971-04-19 GB GB2233671A patent/GB1346787A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7102765A (enExample) | 1971-09-07 |
| FR2081668A1 (enExample) | 1971-12-10 |
| CA943296A (en) | 1974-03-05 |
| FR2081668B1 (enExample) | 1974-10-11 |
| GB1346787A (en) | 1974-02-13 |
| BE763723A (fr) | 1971-08-02 |
| US3758434A (en) | 1973-09-11 |
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