JPH0464627B2 - - Google Patents
Info
- Publication number
- JPH0464627B2 JPH0464627B2 JP61235889A JP23588986A JPH0464627B2 JP H0464627 B2 JPH0464627 B2 JP H0464627B2 JP 61235889 A JP61235889 A JP 61235889A JP 23588986 A JP23588986 A JP 23588986A JP H0464627 B2 JPH0464627 B2 JP H0464627B2
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- aminophenoxy
- bis
- polyetheramide
- group
- 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 - Lifetime
Links
- 229920000642 polymer Polymers 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 24
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 17
- 238000009835 boiling Methods 0.000 claims description 14
- -1 ether compound Chemical class 0.000 claims description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 150000004985 diamines Chemical class 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 26
- 239000001294 propane Substances 0.000 description 17
- 229920002614 Polyether block amide Polymers 0.000 description 13
- 150000003949 imides Chemical class 0.000 description 13
- 239000002904 solvent Substances 0.000 description 9
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- 239000003960 organic solvent Substances 0.000 description 6
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000004962 Polyamide-imide Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000004984 aromatic diamines Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 229920002312 polyamide-imide Polymers 0.000 description 3
- 239000011342 resin composition Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- KMKWGXGSGPYISJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 KMKWGXGSGPYISJ-UHFFFAOYSA-N 0.000 description 2
- MERJBUUXKYLFCB-UHFFFAOYSA-N 4-[4-[[4-(4-aminophenoxy)-3,5-dichlorophenyl]methyl]-2,6-dichlorophenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C(=C1)Cl)=C(Cl)C=C1CC(C=C1Cl)=CC(Cl)=C1OC1=CC=C(N)C=C1 MERJBUUXKYLFCB-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000002411 adverse Effects 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 125000006159 dianhydride group Chemical group 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 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
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 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
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000012643 polycondensation polymerization Methods 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NJMOHBDCGXJLNJ-UHFFFAOYSA-N trimellitic anhydride chloride Chemical compound ClC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 NJMOHBDCGXJLNJ-UHFFFAOYSA-N 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- GKKUVAJSHWPSBO-UHFFFAOYSA-N 2,5-bis(methoxycarbonyl)benzoic acid Chemical compound COC(=O)C1=CC=C(C(=O)OC)C(C(O)=O)=C1 GKKUVAJSHWPSBO-UHFFFAOYSA-N 0.000 description 1
- MTVRACIHAHWZEW-UHFFFAOYSA-N 2-phenoxycarbonylterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(=O)OC=2C=CC=CC=2)=C1 MTVRACIHAHWZEW-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- JQSRUJUKMCULGS-UHFFFAOYSA-N 4-[4-[1-[4-(4-aminophenoxy)-3,5-dibromophenyl]propyl]-2,6-dibromophenoxy]aniline Chemical compound C=1C(Br)=C(OC=2C=CC(N)=CC=2)C(Br)=CC=1C(CC)C(C=C1Br)=CC(Br)=C1OC1=CC=C(N)C=C1 JQSRUJUKMCULGS-UHFFFAOYSA-N 0.000 description 1
- FFNFABFQQRJHSY-UHFFFAOYSA-N 4-[4-[1-[4-(4-aminophenoxy)-3,5-dichlorophenyl]ethyl]-2,6-dichlorophenoxy]aniline Chemical compound C=1C(Cl)=C(OC=2C=CC(N)=CC=2)C(Cl)=CC=1C(C)C(C=C1Cl)=CC(Cl)=C1OC1=CC=C(N)C=C1 FFNFABFQQRJHSY-UHFFFAOYSA-N 0.000 description 1
- HHVHOJOGTRADFI-UHFFFAOYSA-N 4-[4-[1-[4-(4-aminophenoxy)-3,5-dimethoxyphenyl]ethyl]-2,6-dimethoxyphenoxy]aniline Chemical compound COC1=CC(C(C)C=2C=C(OC)C(OC=3C=CC(N)=CC=3)=C(OC)C=2)=CC(OC)=C1OC1=CC=C(N)C=C1 HHVHOJOGTRADFI-UHFFFAOYSA-N 0.000 description 1
- XXBIBSRALRGHMT-UHFFFAOYSA-N 4-[4-[1-[4-(4-aminophenoxy)-3,5-dimethylphenyl]ethyl]-2,6-dimethylphenoxy]aniline Chemical compound C=1C(C)=C(OC=2C=CC(N)=CC=2)C(C)=CC=1C(C)C(C=C1C)=CC(C)=C1OC1=CC=C(N)C=C1 XXBIBSRALRGHMT-UHFFFAOYSA-N 0.000 description 1
- CKXLOUZITCMXEJ-UHFFFAOYSA-N 4-[4-[1-[4-(4-aminophenoxy)-3,5-dimethylphenyl]propyl]-2,6-dimethylphenoxy]aniline Chemical compound C=1C(C)=C(OC=2C=CC(N)=CC=2)C(C)=CC=1C(CC)C(C=C1C)=CC(C)=C1OC1=CC=C(N)C=C1 CKXLOUZITCMXEJ-UHFFFAOYSA-N 0.000 description 1
- LQBGEDCIHJHVMC-UHFFFAOYSA-N 4-[4-[1-[4-(4-aminophenoxy)-3-butan-2-ylphenyl]ethyl]-2-butan-2-ylphenoxy]aniline Chemical compound CCC(C)C1=CC(C(C)C=2C=C(C(OC=3C=CC(N)=CC=3)=CC=2)C(C)CC)=CC=C1OC1=CC=C(N)C=C1 LQBGEDCIHJHVMC-UHFFFAOYSA-N 0.000 description 1
- UXFMETGWCNLEJX-UHFFFAOYSA-N 4-[4-[1-[4-(4-aminophenoxy)-3-ethoxyphenyl]ethyl]-2-ethoxyphenoxy]aniline Chemical compound CCOC1=CC(C(C)C=2C=C(OCC)C(OC=3C=CC(N)=CC=3)=CC=2)=CC=C1OC1=CC=C(N)C=C1 UXFMETGWCNLEJX-UHFFFAOYSA-N 0.000 description 1
- OGLMAPFKTLOPHM-UHFFFAOYSA-N 4-[4-[1-[4-(4-aminophenoxy)-3-methoxyphenyl]ethyl]-2-methoxyphenoxy]aniline Chemical compound COC1=CC(C(C)C=2C=C(OC)C(OC=3C=CC(N)=CC=3)=CC=2)=CC=C1OC1=CC=C(N)C=C1 OGLMAPFKTLOPHM-UHFFFAOYSA-N 0.000 description 1
- DDUOTTYELMRWJE-UHFFFAOYSA-N 4-[4-[1-[4-(4-aminophenoxy)phenyl]propyl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(CC)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 DDUOTTYELMRWJE-UHFFFAOYSA-N 0.000 description 1
- BZIWJKPYZLPVIN-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)-3,5-dibromophenyl]-1,1,1,3,3,3-hexachloropropan-2-yl]-2,6-dibromophenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=C(Br)C=C(C(C=2C=C(Br)C(OC=3C=CC(N)=CC=3)=C(Br)C=2)(C(Cl)(Cl)Cl)C(Cl)(Cl)Cl)C=C1Br BZIWJKPYZLPVIN-UHFFFAOYSA-N 0.000 description 1
- MUDNCBUJHBRRME-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)-3,5-dibromophenyl]butan-2-yl]-2,6-dibromophenoxy]aniline Chemical compound C=1C(Br)=C(OC=2C=CC(N)=CC=2)C(Br)=CC=1C(C)(CC)C(C=C1Br)=CC(Br)=C1OC1=CC=C(N)C=C1 MUDNCBUJHBRRME-UHFFFAOYSA-N 0.000 description 1
- LRCIDTOMCOTLFJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)-3,5-dichlorophenyl]propan-2-yl]-2,6-dichlorophenoxy]aniline Chemical compound C=1C(Cl)=C(OC=2C=CC(N)=CC=2)C(Cl)=CC=1C(C)(C)C(C=C1Cl)=CC(Cl)=C1OC1=CC=C(N)C=C1 LRCIDTOMCOTLFJ-UHFFFAOYSA-N 0.000 description 1
- ABCHJRPSNNTRGG-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)-3,5-dimethylphenyl]-1,1,1,3,3,3-hexachloropropan-2-yl]-2,6-dimethylphenoxy]aniline Chemical compound CC1=CC(C(C=2C=C(C)C(OC=3C=CC(N)=CC=3)=C(C)C=2)(C(Cl)(Cl)Cl)C(Cl)(Cl)Cl)=CC(C)=C1OC1=CC=C(N)C=C1 ABCHJRPSNNTRGG-UHFFFAOYSA-N 0.000 description 1
- VCFYKCXKADGLPS-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)-3,5-dimethylphenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]-2,6-dimethylphenoxy]aniline Chemical compound CC1=CC(C(C=2C=C(C)C(OC=3C=CC(N)=CC=3)=C(C)C=2)(C(F)(F)F)C(F)(F)F)=CC(C)=C1OC1=CC=C(N)C=C1 VCFYKCXKADGLPS-UHFFFAOYSA-N 0.000 description 1
- UCGUBZDRPKFHQJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)-3,5-dimethylphenyl]butan-2-yl]-2,6-dimethylphenoxy]aniline Chemical compound C=1C(C)=C(OC=2C=CC(N)=CC=2)C(C)=CC=1C(C)(CC)C(C=C1C)=CC(C)=C1OC1=CC=C(N)C=C1 UCGUBZDRPKFHQJ-UHFFFAOYSA-N 0.000 description 1
- BVDPIHNAIJHQJK-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)-3-methylphenyl]butan-2-yl]-2-methylphenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C(C)=CC=1C(C)(CC)C(C=C1C)=CC=C1OC1=CC=C(N)C=C1 BVDPIHNAIJHQJK-UHFFFAOYSA-N 0.000 description 1
- VMQLIXASFYNCAZ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]-1,1,1,3,3,3-hexachloropropan-2-yl]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C(C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)(C(Cl)(Cl)Cl)C(Cl)(Cl)Cl)C=C1 VMQLIXASFYNCAZ-UHFFFAOYSA-N 0.000 description 1
- HHLMWQDRYZAENA-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C(C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)(C(F)(F)F)C(F)(F)F)C=C1 HHLMWQDRYZAENA-UHFFFAOYSA-N 0.000 description 1
- UXBSLADVESNJEO-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]butan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(CC)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 UXBSLADVESNJEO-UHFFFAOYSA-N 0.000 description 1
- BGKBJXVVPZPBPS-UHFFFAOYSA-N 4-[4-[3-[4-(4-aminophenoxy)-3,5-dibromophenyl]pentan-3-yl]-2,6-dibromophenoxy]aniline Chemical compound C=1C(Br)=C(OC=2C=CC(N)=CC=2)C(Br)=CC=1C(CC)(CC)C(C=C1Br)=CC(Br)=C1OC1=CC=C(N)C=C1 BGKBJXVVPZPBPS-UHFFFAOYSA-N 0.000 description 1
- ZPBCBNPCENPLRR-UHFFFAOYSA-N 4-[4-[3-[4-(4-aminophenoxy)-3,5-dimethylphenyl]pentan-3-yl]-2,6-dimethylphenoxy]aniline Chemical compound C=1C(C)=C(OC=2C=CC(N)=CC=2)C(C)=CC=1C(CC)(CC)C(C=C1C)=CC(C)=C1OC1=CC=C(N)C=C1 ZPBCBNPCENPLRR-UHFFFAOYSA-N 0.000 description 1
- OYGQSMMPUFNMOL-UHFFFAOYSA-N 4-[4-[3-[4-(4-aminophenoxy)phenyl]pentan-3-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(CC)(CC)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 OYGQSMMPUFNMOL-UHFFFAOYSA-N 0.000 description 1
- AHRMJPFSPITREJ-UHFFFAOYSA-N 4-[4-[[4-(4-aminophenoxy)-3,5-dibromophenyl]methyl]-2,6-dibromophenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C(=C1)Br)=C(Br)C=C1CC(C=C1Br)=CC(Br)=C1OC1=CC=C(N)C=C1 AHRMJPFSPITREJ-UHFFFAOYSA-N 0.000 description 1
- DJWLNSOSQFGSPR-UHFFFAOYSA-N 4-[4-[[4-(4-aminophenoxy)-3,5-dimethoxyphenyl]methyl]-2,6-dimethoxyphenoxy]aniline Chemical compound C=1C(OC)=C(OC=2C=CC(N)=CC=2)C(OC)=CC=1CC(C=C1OC)=CC(OC)=C1OC1=CC=C(N)C=C1 DJWLNSOSQFGSPR-UHFFFAOYSA-N 0.000 description 1
- NAUSGUYYKKTJTC-UHFFFAOYSA-N 4-[4-[[4-(4-aminophenoxy)-3,5-dimethylphenyl]methyl]-2,6-dimethylphenoxy]aniline Chemical compound C=1C(C)=C(OC=2C=CC(N)=CC=2)C(C)=CC=1CC(C=C1C)=CC(C)=C1OC1=CC=C(N)C=C1 NAUSGUYYKKTJTC-UHFFFAOYSA-N 0.000 description 1
- QKUAKQMWPFGQKF-UHFFFAOYSA-N 4-[4-[[4-(4-aminophenoxy)-3-bromophenyl]methyl]-2-bromophenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C(=C1)Br)=CC=C1CC(C=C1Br)=CC=C1OC1=CC=C(N)C=C1 QKUAKQMWPFGQKF-UHFFFAOYSA-N 0.000 description 1
- JVRUJVDAQPOKQK-UHFFFAOYSA-N 4-[4-[[4-(4-aminophenoxy)-3-butan-2-ylphenyl]methyl]-2-butan-2-ylphenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C(C(C)CC)=CC=1CC(C=C1C(C)CC)=CC=C1OC1=CC=C(N)C=C1 JVRUJVDAQPOKQK-UHFFFAOYSA-N 0.000 description 1
- GVQXABVNAZYPPO-UHFFFAOYSA-N 4-[4-[[4-(4-aminophenoxy)-3-butylphenyl]methyl]-2-butylphenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C(CCCC)=CC=1CC(C=C1CCCC)=CC=C1OC1=CC=C(N)C=C1 GVQXABVNAZYPPO-UHFFFAOYSA-N 0.000 description 1
- GNXCXJSOIPQQQO-UHFFFAOYSA-N 4-[4-[[4-(4-aminophenoxy)-3-chloro-5-methylphenyl]methyl]-2-chloro-6-methylphenoxy]aniline Chemical compound C=1C(Cl)=C(OC=2C=CC(N)=CC=2)C(C)=CC=1CC(C=C1Cl)=CC(C)=C1OC1=CC=C(N)C=C1 GNXCXJSOIPQQQO-UHFFFAOYSA-N 0.000 description 1
- KODXTKOQSKLENE-UHFFFAOYSA-N 4-[4-[[4-(4-aminophenoxy)-3-chlorophenyl]methyl]-2-chlorophenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C(=C1)Cl)=CC=C1CC(C=C1Cl)=CC=C1OC1=CC=C(N)C=C1 KODXTKOQSKLENE-UHFFFAOYSA-N 0.000 description 1
- VTAGQGXKYIEILE-UHFFFAOYSA-N 4-[4-[[4-(4-aminophenoxy)-3-ethoxyphenyl]methyl]-2-ethoxyphenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C(OCC)=CC=1CC(C=C1OCC)=CC=C1OC1=CC=C(N)C=C1 VTAGQGXKYIEILE-UHFFFAOYSA-N 0.000 description 1
- VOLMTHGTXQJBFP-UHFFFAOYSA-N 4-[4-[[4-(4-aminophenoxy)-3-ethylphenyl]methyl]-2-ethylphenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C(CC)=CC=1CC(C=C1CC)=CC=C1OC1=CC=C(N)C=C1 VOLMTHGTXQJBFP-UHFFFAOYSA-N 0.000 description 1
- HPQWYQJUPFZCRW-UHFFFAOYSA-N 4-[4-[[4-(4-aminophenoxy)-3-methoxyphenyl]methyl]-2-methoxyphenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C(OC)=CC=1CC(C=C1OC)=CC=C1OC1=CC=C(N)C=C1 HPQWYQJUPFZCRW-UHFFFAOYSA-N 0.000 description 1
- GJCJZNPUDLWINR-UHFFFAOYSA-N 4-[4-[[4-(4-aminophenoxy)-3-methylphenyl]methyl]-2-methylphenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C(C)=CC=1CC(C=C1C)=CC=C1OC1=CC=C(N)C=C1 GJCJZNPUDLWINR-UHFFFAOYSA-N 0.000 description 1
- KDCQSYVKWSQKAD-UHFFFAOYSA-N 4-[4-[[4-(4-aminophenoxy)-3-propan-2-ylphenyl]methyl]-2-propan-2-ylphenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C(C(C)C)=CC=1CC(C=C1C(C)C)=CC=C1OC1=CC=C(N)C=C1 KDCQSYVKWSQKAD-UHFFFAOYSA-N 0.000 description 1
- XVNIYRQVAVHATD-UHFFFAOYSA-N 4-[4-[[4-(4-aminophenoxy)-3-propylphenyl]methyl]-2-propylphenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C(CCC)=CC=1CC(C=C1CCC)=CC=C1OC1=CC=C(N)C=C1 XVNIYRQVAVHATD-UHFFFAOYSA-N 0.000 description 1
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 102100029647 Apoptosis-associated speck-like protein containing a CARD Human genes 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
- 101000728679 Homo sapiens Apoptosis-associated speck-like protein containing a CARD Proteins 0.000 description 1
- 101000707471 Homo sapiens Serine incorporator 3 Proteins 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000012674 dispersion polymerization Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012772 electrical insulation material Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000012673 precipitation polymerization Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8704841A GB2195645B (en) | 1986-10-03 | 1987-03-02 | Polyetheramide-imide polymer composition |
| US07/020,885 US4791157A (en) | 1986-10-03 | 1987-03-02 | Polyetheramide-imide polymer composition |
| KR1019870002121A KR900002536B1 (ko) | 1986-10-03 | 1987-03-10 | 폴리에테르아미드-이미드 중합체 조성물 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28478685 | 1985-12-18 | ||
| JP60-284786 | 1985-12-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62270625A JPS62270625A (ja) | 1987-11-25 |
| JPH0464627B2 true JPH0464627B2 (fr) | 1992-10-15 |
Family
ID=17682998
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23588986A Granted JPS62270625A (ja) | 1985-12-18 | 1986-10-03 | ポリエ−テルアミドイミド重合体組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62270625A (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4861855A (en) * | 1987-03-31 | 1989-08-29 | Amoco Corporation | Polyamide-imide compositions from bisphenoxyphenyl diamine tricarboxylic anhydride and tetracarboxylic dianhydride |
| JP2866654B2 (ja) * | 1988-04-20 | 1999-03-08 | 日立化成工業株式会社 | ホツトメルト接着剤，ホツトメルト接着剤層付ポリイミドフイルム及び印刷回路用基板 |
| US5344895A (en) * | 1993-04-01 | 1994-09-06 | University Of Massachusetts Lowell | Polyamideimide composition with improved processability |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5653573A (en) * | 1979-10-09 | 1981-05-13 | Toshiba Corp | Protection for thyristor converter |
| JPS5764955A (en) * | 1980-10-08 | 1982-04-20 | Hitachi Ltd | Semiconductor device |
| JPS59202259A (ja) * | 1983-04-30 | 1984-11-16 | Hitachi Chem Co Ltd | 芳香族ポリエ−テルアミドイミド重合体ワニス |
-
1986
- 1986-10-03 JP JP23588986A patent/JPS62270625A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5653573A (en) * | 1979-10-09 | 1981-05-13 | Toshiba Corp | Protection for thyristor converter |
| JPS5764955A (en) * | 1980-10-08 | 1982-04-20 | Hitachi Ltd | Semiconductor device |
| JPS59202259A (ja) * | 1983-04-30 | 1984-11-16 | Hitachi Chem Co Ltd | 芳香族ポリエ−テルアミドイミド重合体ワニス |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62270625A (ja) | 1987-11-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |