DE2247733A1 - Neue aromatische polyimide mit karbinolkettenverknuepfung, verfahren zu ihrer herstellung sowie deren anwendung - Google Patents
Neue aromatische polyimide mit karbinolkettenverknuepfung, verfahren zu ihrer herstellung sowie deren anwendungInfo
- Publication number
- DE2247733A1 DE2247733A1 DE19722247733 DE2247733A DE2247733A1 DE 2247733 A1 DE2247733 A1 DE 2247733A1 DE 19722247733 DE19722247733 DE 19722247733 DE 2247733 A DE2247733 A DE 2247733A DE 2247733 A1 DE2247733 A1 DE 2247733A1
- Authority
- DE
- Germany
- Prior art keywords
- aromatic
- general formula
- choh
- carbinol
- aromatic polyimide
- 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
- 239000004642 Polyimide Substances 0.000 title claims description 24
- 229920001721 polyimide Polymers 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 150000004985 diamines Chemical class 0.000 claims description 12
- -1 hydroxymethylene Chemical group 0.000 claims description 7
- 239000000853 adhesive Substances 0.000 claims description 3
- 230000001070 adhesive effect Effects 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000002131 composite material Substances 0.000 claims description 3
- 150000005690 diesters Chemical class 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000004922 lacquer Substances 0.000 claims description 2
- 239000003495 polar organic solvent Substances 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000003949 imides Chemical group 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IZMXTQMBKGJCPB-UHFFFAOYSA-N CC(C(=O)N(C)C)(OS(=O)(=O)O)C Chemical compound CC(C(=O)N(C)C)(OS(=O)(=O)O)C IZMXTQMBKGJCPB-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 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 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000002966 varnish 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Indole Compounds (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7122967A FR2142716B2 (enExample) | 1971-06-23 | 1971-06-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2247733A1 true DE2247733A1 (de) | 1973-12-13 |
Family
ID=9079195
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722247733 Pending DE2247733A1 (de) | 1971-06-23 | 1972-06-21 | Neue aromatische polyimide mit karbinolkettenverknuepfung, verfahren zu ihrer herstellung sowie deren anwendung |
| DE19722230352 Pending DE2230352A1 (de) | 1971-06-23 | 1972-06-21 | Para-phenylen-bis-hydroxymethylen-4phthalsaeure sowie deren ester |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722230352 Pending DE2230352A1 (de) | 1971-06-23 | 1972-06-21 | Para-phenylen-bis-hydroxymethylen-4phthalsaeure sowie deren ester |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4927598A (enExample) |
| BE (1) | BE784907R (enExample) |
| DE (2) | DE2247733A1 (enExample) |
| FR (1) | FR2142716B2 (enExample) |
| GB (1) | GB1357705A (enExample) |
| IT (1) | IT1044849B (enExample) |
| NL (1) | NL7208646A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2723099A1 (fr) * | 1994-07-27 | 1996-02-02 | Centre Etu Mat Organ Tech Avan | Polyimides photosensibles negatifs compositions en contenant et leurs applications |
| CN1034343C (zh) * | 1991-12-10 | 1997-03-26 | 武汉市解放化工厂 | 一种干酪素-尼龙粘合剂的制造方法 |
-
1971
- 1971-06-23 FR FR7122967A patent/FR2142716B2/fr not_active Expired
-
1972
- 1972-06-15 BE BE784907A patent/BE784907R/xx active
- 1972-06-21 DE DE19722247733 patent/DE2247733A1/de active Pending
- 1972-06-21 DE DE19722230352 patent/DE2230352A1/de active Pending
- 1972-06-22 GB GB2934972A patent/GB1357705A/en not_active Expired
- 1972-06-23 IT IT2608372A patent/IT1044849B/it active
- 1972-06-23 JP JP6363972A patent/JPS4927598A/ja active Pending
- 1972-06-23 NL NL7208646A patent/NL7208646A/xx not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1034343C (zh) * | 1991-12-10 | 1997-03-26 | 武汉市解放化工厂 | 一种干酪素-尼龙粘合剂的制造方法 |
| FR2723099A1 (fr) * | 1994-07-27 | 1996-02-02 | Centre Etu Mat Organ Tech Avan | Polyimides photosensibles negatifs compositions en contenant et leurs applications |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4927598A (enExample) | 1974-03-12 |
| IT1044849B (it) | 1980-04-21 |
| FR2142716A2 (enExample) | 1973-02-02 |
| BE784907R (fr) | 1972-10-02 |
| DE2230352A1 (de) | 1973-03-29 |
| GB1357705A (en) | 1974-06-26 |
| FR2142716B2 (enExample) | 1973-06-29 |
| NL7208646A (enExample) | 1972-12-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |