DE2203153C3 - Verfahren zur Herstellung von linearen aromatischen Polyamidimiden - Google Patents
Verfahren zur Herstellung von linearen aromatischen PolyamidimidenInfo
- Publication number
- DE2203153C3 DE2203153C3 DE19722203153 DE2203153A DE2203153C3 DE 2203153 C3 DE2203153 C3 DE 2203153C3 DE 19722203153 DE19722203153 DE 19722203153 DE 2203153 A DE2203153 A DE 2203153A DE 2203153 C3 DE2203153 C3 DE 2203153C3
- Authority
- DE
- Germany
- Prior art keywords
- mol
- aromatic
- groups
- imide
- preparation
- 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 16
- 238000002360 preparation method Methods 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 11
- 239000004962 Polyamide-imide Substances 0.000 title claims description 4
- 229920002312 polyamide-imide Polymers 0.000 title claims description 4
- 125000005442 diisocyanate group Chemical group 0.000 claims description 18
- 125000005462 imide group Chemical group 0.000 claims description 17
- 229920000642 polymer Polymers 0.000 claims description 17
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 15
- 150000004985 diamines Chemical class 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 10
- 229910000071 diazene Inorganic materials 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims description 5
- 150000003949 imides Chemical class 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- -1 imide groups Dicarboxylic acids Chemical class 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- 238000004821 distillation Methods 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 238000001757 thermogravimetry curve Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 230000001174 ascending effect Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- GRGRGLVMGTVCNZ-UHFFFAOYSA-N dmmda Chemical compound COC1=CC(CC(C)N)=C(OC)C2=C1OCO2 GRGRGLVMGTVCNZ-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003628 tricarboxylic acids Chemical class 0.000 description 2
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- BUZMJVBOGDBMGI-UHFFFAOYSA-N 1-phenylpropylbenzene Chemical compound C=1C=CC=CC=1C(CC)C1=CC=CC=C1 BUZMJVBOGDBMGI-UHFFFAOYSA-N 0.000 description 1
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 1
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 description 1
- WECDUOXQLAIPQW-UHFFFAOYSA-N 4,4'-Methylene bis(2-methylaniline) Chemical compound C1=C(N)C(C)=CC(CC=2C=C(C)C(N)=CC=2)=C1 WECDUOXQLAIPQW-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-M 4-aminobenzoate Chemical compound NC1=CC=C(C([O-])=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910006644 SnIV Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 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
- 239000000194 fatty acid Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- VWBWQOUWDOULQN-UHFFFAOYSA-N nmp n-methylpyrrolidone Chemical compound CN1CCCC1=O.CN1CCCC1=O VWBWQOUWDOULQN-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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/341—Dicarboxylic acids, esters of polycarboxylic acids containing two carboxylic acid groups
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3821—Carboxylic acids; Esters thereof with monohydroxyl compounds
-
- 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
- C08G73/14—Polyamide-imides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT176471A AT311516B (de) | 1971-03-02 | 1971-03-02 | Verfahren zur Herstellung stabile Lacklösungen ergebender linearer Polyamidimide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2203153A1 DE2203153A1 (de) | 1972-09-21 |
| DE2203153B2 DE2203153B2 (de) | 1981-07-23 |
| DE2203153C3 true DE2203153C3 (de) | 1982-04-22 |
Family
ID=3520502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722203153 Expired DE2203153C3 (de) | 1971-03-02 | 1972-01-24 | Verfahren zur Herstellung von linearen aromatischen Polyamidimiden |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5229358B1 (enExample) |
| AT (1) | AT311516B (enExample) |
| DE (1) | DE2203153C3 (enExample) |
| FR (1) | FR2128433B1 (enExample) |
| GB (1) | GB1383813A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5697612U (enExample) * | 1979-12-27 | 1981-08-03 | ||
| JPS576113A (en) * | 1980-06-11 | 1982-01-13 | Akira Kobayashi | Ceiling hanging metals |
| DE10303635A1 (de) | 2003-01-30 | 2004-12-02 | Altana Electrical Insulation Gmbh | Verfahren zur Herstellung lagerstabiler Polyamidimid-Harze und Überzugsmittel, die diese enthalten |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1181446A (en) * | 1966-07-22 | 1970-02-18 | Hitachi Chemical Co Ltd | Process for producing Amide-Imide Resins |
| AT270224B (de) * | 1967-03-20 | 1969-04-25 | Beck & Co Ag Dr | Verfahren zur Herstellung von neuen thermostabilen, linearen Polyamidimiden |
| JPS5033120A (enExample) * | 1973-07-27 | 1975-03-31 |
-
1971
- 1971-03-02 AT AT176471A patent/AT311516B/de not_active IP Right Cessation
-
1972
- 1972-01-24 DE DE19722203153 patent/DE2203153C3/de not_active Expired
- 1972-02-25 GB GB875372A patent/GB1383813A/en not_active Expired
- 1972-02-29 FR FR7206917A patent/FR2128433B1/fr not_active Expired
- 1972-03-02 JP JP47021118A patent/JPS5229358B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1383813A (en) | 1974-02-12 |
| AT311516B (de) | 1973-11-26 |
| DE2203153A1 (de) | 1972-09-21 |
| DE2203153B2 (de) | 1981-07-23 |
| JPS5229358B1 (enExample) | 1977-08-01 |
| FR2128433B1 (enExample) | 1975-02-21 |
| FR2128433A1 (enExample) | 1972-10-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH437788A (de) | Verfahren zur Herstellung eines Polyamidharzes | |
| CH457850A (de) | Verfahren zur Herstellung von Amidgruppen aufweisenden Polyimiden und Anwendung des Verfahrens | |
| DE2537330A1 (de) | Halbleitervorrichtung und verfahren zu ihrer herstellung | |
| DE2904801A1 (de) | Verfahren zur herstellung eines zwischenproduktes vom polamidsaeuretyp fuer die herstellung von halbleitern | |
| DE2331380A1 (de) | Polyamidimide und verfahren zu deren herstellung | |
| DE1770146C3 (de) | Verfahren zur Herstellung von PoIy-(arylen-triketoimidazolidinen) | |
| EP0049393B1 (de) | Hitzehärtbare, Amid- und Imidgruppen enthaltende Poly-Kondensationsprodukte und ihre Verwendung | |
| DE2203153C3 (de) | Verfahren zur Herstellung von linearen aromatischen Polyamidimiden | |
| DE3490169C2 (enExample) | ||
| CH463779A (de) | Stabilisierte Polyamidsäurelösung mit verbesserten Viskositätseigenschaften und Verfahren zur Herstellung derselben | |
| DE2039448B2 (de) | Verfahren zur Herstellung von Polyamidimiden | |
| EP0226968B1 (de) | Verfahren zur Herstellung lagerstabiler Polyamidimidlacke und deren Verwendung | |
| DE1940065C3 (de) | Verfahren zur Verminderung der Viskosität von Polytrimellithamidimidlösungen | |
| DE2152972A1 (de) | Wässrige Polyimidzusammensetzungen | |
| DE2005587C3 (de) | Aromatische Polyimide mit Karbinolkettenverknüpfung sowie deren Anwendung | |
| DE3240934C2 (enExample) | ||
| DE1795611C3 (de) | Formbare polymere Masse | |
| DE2714416A1 (de) | Verfahren zum stabilisieren einer wasserloeslichen zusammensetzung | |
| DE3332032A1 (de) | Spezielle polyamidimide | |
| DE1720909B2 (de) | Verfahren zur Herstellung von PoIyamidimiden | |
| DE1031510B (de) | Verfahren zur Herstellung von Polypyromellithsaeureimiden | |
| DE1645396A1 (de) | Verfahren zur Herstellung von Polyamid-Imiden | |
| DE1646124C3 (de) | Beschichtungslösung aus aromatischen Polytrimellithamidsäuren und ihre Verwendung zur Herstellung von Beschichtungen | |
| DE2031072B2 (de) | Verfahren zur herstellung von polyamidimidloesungen | |
| DE2433907C2 (de) | Polymere Imidazolone |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |