DE2228832A1 - Neue aromatische Polyimide mit Kar binolkettenverknupfung, Verfahren zu ihrer Herstellung sowie deren Anwendung - Google Patents
Neue aromatische Polyimide mit Kar binolkettenverknupfung, Verfahren zu ihrer Herstellung sowie deren AnwendungInfo
- Publication number
- DE2228832A1 DE2228832A1 DE19722228832 DE2228832A DE2228832A1 DE 2228832 A1 DE2228832 A1 DE 2228832A1 DE 19722228832 DE19722228832 DE 19722228832 DE 2228832 A DE2228832 A DE 2228832A DE 2228832 A1 DE2228832 A1 DE 2228832A1
- Authority
- DE
- Germany
- Prior art keywords
- organic solvent
- polar organic
- carbinol
- aromatic
- solution
- 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
- 238000000034 method Methods 0.000 title claims description 14
- 239000004642 Polyimide Substances 0.000 title claims description 10
- 125000003118 aryl group Chemical group 0.000 title claims description 10
- 229920001721 polyimide Polymers 0.000 title claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000003495 polar organic solvent Substances 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 6
- 229940100630 metacresol Drugs 0.000 claims description 6
- 150000004985 diamines Chemical class 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- -1 allcyclic Chemical group 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims 1
- 239000004952 Polyamide Substances 0.000 claims 1
- 150000004984 aromatic diamines Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 229930003836 cresol Natural products 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 229920002647 polyamide Polymers 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SXXCGBHCECOZBP-UHFFFAOYSA-N 5-(hydroxymethylidene)cyclohexa-1,3-diene-1,2-dicarboxylic acid Chemical compound OC=C1CC(=C(C(=O)O)C=C1)C(=O)O SXXCGBHCECOZBP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 239000008096 xylene 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)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7122154A FR2141592B2 (cs) | 1971-06-17 | 1971-06-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2228832A1 true DE2228832A1 (de) | 1972-12-21 |
Family
ID=9078863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722228832 Pending DE2228832A1 (de) | 1971-06-17 | 1972-06-14 | Neue aromatische Polyimide mit Kar binolkettenverknupfung, Verfahren zu ihrer Herstellung sowie deren Anwendung |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE783906A (cs) |
| DE (1) | DE2228832A1 (cs) |
| FR (1) | FR2141592B2 (cs) |
| GB (1) | GB1357704A (cs) |
| IT (1) | IT998071B (cs) |
| NL (1) | NL7208302A (cs) |
-
1971
- 1971-06-17 FR FR7122154A patent/FR2141592B2/fr not_active Expired
-
1972
- 1972-05-25 BE BE783906A patent/BE783906A/xx unknown
- 1972-06-14 DE DE19722228832 patent/DE2228832A1/de active Pending
- 1972-06-16 NL NL7208302A patent/NL7208302A/xx not_active Application Discontinuation
- 1972-06-16 GB GB2837372A patent/GB1357704A/en not_active Expired
- 1972-06-17 IT IT2582672A patent/IT998071B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| FR2141592A2 (cs) | 1973-01-26 |
| GB1357704A (en) | 1974-06-26 |
| BE783906A (fr) | 1972-11-27 |
| FR2141592B2 (cs) | 1974-03-22 |
| IT998071B (it) | 1976-01-20 |
| NL7208302A (cs) | 1972-12-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2604265C3 (de) | Wässrige Polyamidsäurelösung | |
| DE2439006C2 (de) | Verfahren zur Herstellung von Polyätherimid | |
| DE1931602B2 (de) | Verfahren zur Herstellung von Polytrimellithimiden | |
| DE1768439A1 (de) | Verfahren zur fortlaufenden Herstellung organischer Isocyanate | |
| DE2601577A1 (de) | Von phenylindan-diaminen sich ableitende, loesliche polyamid-imide | |
| DE2947117A1 (de) | Polyamidimidharz, verfahren zu seiner herstellung und dessen verwendung | |
| DE2263190A1 (de) | Loesliche polyimide aus aromatischen dianhydriden und 2,4-diaminodiphenylaminen und 2,4-diaminodiphenylsulfiden | |
| DE3246267A1 (de) | Amingruppenhaltige carbonsaeureamide und ihre verwendung als haerter fuer epoxidharze | |
| DE2257996A1 (de) | Loesliche polyimide | |
| DE3875899T2 (de) | Im basischen medium aetzbare polyimid-zusammensetzungen. | |
| DE2706771C2 (cs) | ||
| DE2228832A1 (de) | Neue aromatische Polyimide mit Kar binolkettenverknupfung, Verfahren zu ihrer Herstellung sowie deren Anwendung | |
| DE1943253C3 (de) | Polyamine | |
| DE3213032C2 (cs) | ||
| DE1770837B2 (cs) | ||
| DE2156620A1 (de) | Verfahren zur Herstellung von Imidgruppen-haltigem Material | |
| DE2155161A1 (de) | Härtbare Zusammensetzungen | |
| DE2500106A1 (de) | Verfahren zur herstellung von 1- methyl-3-phenyl-indan | |
| DE2258505A1 (de) | Oxindoldiamine und verfahren zu ihrer herstellung | |
| DE2246111B2 (de) | Verfahren zur Herstellung von Naphthalimid-43-dicarbonsäuren | |
| DE2247733A1 (de) | Neue aromatische polyimide mit karbinolkettenverknuepfung, verfahren zu ihrer herstellung sowie deren anwendung | |
| DE2034389C3 (de) | Verfahren zur Härtung von Epoxiverbindungen | |
| DE1745130C3 (de) | Verfahren zur Herstellung von Polyimiden | |
| DE2601458A1 (de) | Loesliche, von phenylindandiaminen abgeleitete polyamide | |
| EP0104530A2 (de) | Küpenfarbstoffgemische |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |