JP2020164442A - 5つの芳香環を有するジアミノ又はジニトロベンゼン化合物、およびその製造方法、並びにポリイミド - Google Patents
5つの芳香環を有するジアミノ又はジニトロベンゼン化合物、およびその製造方法、並びにポリイミド Download PDFInfo
- Publication number
- JP2020164442A JP2020164442A JP2019065257A JP2019065257A JP2020164442A JP 2020164442 A JP2020164442 A JP 2020164442A JP 2019065257 A JP2019065257 A JP 2019065257A JP 2019065257 A JP2019065257 A JP 2019065257A JP 2020164442 A JP2020164442 A JP 2020164442A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- compound
- carbon atoms
- represented
- 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.)
- Granted
Links
- -1 dinitro-benzene compound Chemical class 0.000 title claims abstract description 77
- 238000004519 manufacturing process Methods 0.000 title claims description 28
- 229920001721 polyimide Polymers 0.000 title claims description 28
- 239000004642 Polyimide Substances 0.000 title claims description 19
- 125000003118 aryl group Chemical group 0.000 title description 8
- IOCXBXZBNOYTLQ-UHFFFAOYSA-N 3-nitrobenzene-1,2-diamine Chemical compound NC1=CC=CC([N+]([O-])=O)=C1N IOCXBXZBNOYTLQ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 159
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 37
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 21
- 125000003277 amino group Chemical group 0.000 claims abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 150000001340 alkali metals Chemical class 0.000 claims description 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 10
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
- 150000002430 hydrocarbons Chemical group 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 150000008065 acid anhydrides Chemical class 0.000 claims description 6
- 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 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims description 2
- MXPYJVUYLVNEBB-UHFFFAOYSA-N 2-[2-(2-carboxybenzoyl)oxycarbonylbenzoyl]oxycarbonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(O)=O MXPYJVUYLVNEBB-UHFFFAOYSA-N 0.000 claims description 2
- WLDQMQOYNIAUGG-UHFFFAOYSA-N 4-[3-[2-[3-(3,4-dicarboxyphenoxy)phenyl]propan-2-yl]phenoxy]phthalic acid Chemical compound C=1C=CC(OC=2C=C(C(C(O)=O)=CC=2)C(O)=O)=CC=1C(C)(C)C(C=1)=CC=CC=1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 WLDQMQOYNIAUGG-UHFFFAOYSA-N 0.000 claims description 2
- ZHBXLZQQVCDGPA-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)sulfonyl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(S(=O)(=O)C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 ZHBXLZQQVCDGPA-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- MQAHXEQUBNDFGI-UHFFFAOYSA-N 5-[4-[2-[4-[(1,3-dioxo-2-benzofuran-5-yl)oxy]phenyl]propan-2-yl]phenoxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC2=CC=C(C=C2)C(C)(C=2C=CC(OC=3C=C4C(=O)OC(=O)C4=CC=3)=CC=2)C)=C1 MQAHXEQUBNDFGI-UHFFFAOYSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 41
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 22
- 239000002904 solvent Substances 0.000 description 17
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 16
- 238000001097 direct analysis in real time mass spectrometry Methods 0.000 description 16
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 16
- 238000006722 reduction reaction Methods 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 12
- 229910052700 potassium Inorganic materials 0.000 description 12
- 239000011591 potassium Substances 0.000 description 12
- 239000002994 raw material Substances 0.000 description 11
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000009719 polyimide resin Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 125000005462 imide group Chemical group 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- JHFOWEGCZWLHNW-UHFFFAOYSA-N 4-fluoro-2-methyl-1-nitrobenzene Chemical compound CC1=CC(F)=CC=C1[N+]([O-])=O JHFOWEGCZWLHNW-UHFFFAOYSA-N 0.000 description 3
- GIXXQTYGFOHYPT-UHFFFAOYSA-N Bisphenol P Chemical compound C=1C=C(C(C)(C)C=2C=CC(O)=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 GIXXQTYGFOHYPT-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 238000004891 communication Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002828 nitro derivatives Chemical class 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- XUCYJGMIICONES-UHFFFAOYSA-N 1-fluoro-2-methyl-4-nitrobenzene Chemical compound CC1=CC([N+]([O-])=O)=CC=C1F XUCYJGMIICONES-UHFFFAOYSA-N 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000004984 aromatic diamines Chemical class 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001955 polyphenylene ether Polymers 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- QHDSBTKCTUXBEG-UHFFFAOYSA-N 2-[2-(2-aminophenoxy)phenoxy]aniline Chemical class NC1=CC=CC=C1OC1=CC=CC=C1OC1=CC=CC=C1N QHDSBTKCTUXBEG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
- LXJLFVRAWOOQDR-UHFFFAOYSA-N 3-(3-aminophenoxy)aniline Chemical compound NC1=CC=CC(OC=2C=C(N)C=CC=2)=C1 LXJLFVRAWOOQDR-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
- DKKYOQYISDAQER-UHFFFAOYSA-N 3-[3-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=C(OC=3C=C(N)C=CC=3)C=CC=2)=C1 DKKYOQYISDAQER-UHFFFAOYSA-N 0.000 description 1
- WCXGOVYROJJXHA-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenyl]sulfonylphenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)S(=O)(=O)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 WCXGOVYROJJXHA-UHFFFAOYSA-N 0.000 description 1
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
- QYIMZXITLDTULQ-UHFFFAOYSA-N 4-(4-amino-2-methylphenyl)-3-methylaniline Chemical compound CC1=CC(N)=CC=C1C1=CC=C(N)C=C1C QYIMZXITLDTULQ-UHFFFAOYSA-N 0.000 description 1
- PVFQHGDIOXNKIC-UHFFFAOYSA-N 4-[2-[3-[2-(4-hydroxyphenyl)propan-2-yl]phenyl]propan-2-yl]phenol Chemical compound C=1C=CC(C(C)(C)C=2C=CC(O)=CC=2)=CC=1C(C)(C)C1=CC=C(O)C=C1 PVFQHGDIOXNKIC-UHFFFAOYSA-N 0.000 description 1
- WUPRYUDHUFLKFL-UHFFFAOYSA-N 4-[3-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(OC=2C=CC(N)=CC=2)=C1 WUPRYUDHUFLKFL-UHFFFAOYSA-N 0.000 description 1
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 description 1
- RLSMYIFSFZLJQZ-UHFFFAOYSA-N 4-[4-(4-hydroxyphenoxy)phenoxy]phenol Chemical compound C1=CC(O)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(O)C=C1 RLSMYIFSFZLJQZ-UHFFFAOYSA-N 0.000 description 1
- ROXBONJQHNRKST-UHFFFAOYSA-N 4-[4-(9H-fluoren-1-yl)phenoxy]aniline Chemical compound NC1=CC=C(OC2=CC=C(C=C2)C2=CC=CC=3C4=CC=CC=C4CC2=3)C=C1 ROXBONJQHNRKST-UHFFFAOYSA-N 0.000 description 1
- 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 1
- UTDAGHZGKXPRQI-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenyl]sulfonylphenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(S(=O)(=O)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 UTDAGHZGKXPRQI-UHFFFAOYSA-N 0.000 description 1
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 description 1
- XPAQFJJCWGSXGJ-UHFFFAOYSA-N 4-amino-n-(4-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=C(N)C=C1 XPAQFJJCWGSXGJ-UHFFFAOYSA-N 0.000 description 1
- JAYVFGLJMPUIAH-UHFFFAOYSA-N 5-[2-[3,5-dimethyl-4-(3-methyl-4-nitrophenoxy)phenyl]propan-2-yl]-1,3-dimethyl-2-(3-methyl-4-nitrophenoxy)benzene Chemical compound CC=1C=C(OC2=C(C=C(C=C2C)C(C)(C)C2=CC(=C(C(=C2)C)OC2=CC(=C(C=C2)[N+](=O)[O-])C)C)C)C=CC1[N+](=O)[O-] JAYVFGLJMPUIAH-UHFFFAOYSA-N 0.000 description 1
- BZBAYMUKLAYQEO-UHFFFAOYSA-N Bc1ccccc1 Chemical compound Bc1ccccc1 BZBAYMUKLAYQEO-UHFFFAOYSA-N 0.000 description 1
- JFOSPOYVPBTMCL-SOFGYWHQSA-N CC(/C=C(\C=C=[IH])/[N+]([O-])=O)C=C=[IH] Chemical compound CC(/C=C(\C=C=[IH])/[N+]([O-])=O)C=C=[IH] JFOSPOYVPBTMCL-SOFGYWHQSA-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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N [O-][N+](c1ccccc1)=O Chemical compound [O-][N+](c1ccccc1)=O LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N c(cc1)ccc1-c1cc(-c2ccccc2)ccc1 Chemical compound c(cc1)ccc1-c1cc(-c2ccccc2)ccc1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000375 direct analysis in real time Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000012063 dual-affinity re-targeting Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 239000003779 heat-resistant material Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Description
但し、下記式(a)〜(d)で表される化合物を除く。
(1)下記式(1−a)で表されるジアミン化合物の製造方法
該ジアミン化合物の製造方法は何ら制限されるものではなく、いかなる方法で製造してもよい。例えば、下記一般式(1−b)又は(1−c)又は(1−d)で表される化合物のニトロ基を還元することにより得ることが出来る。
上記一般式(1−b)又は(1−c)又は(1−d)で表される(ジ)ニトロ化合物の製造方法は、何ら制限されるものではなく、いかなる方法で製造してもよい。好ましくは、下記一般式(2−a)で示される化合物の一以上と下記一般式(2−b)で示される化合物の一以上と下記一般式(3−a)で示される化合物の一以上とを、有機溶媒中、好ましくは塩基の存在下にて、加温下で脱水縮合反応させることにより、上記一般式(1−b)で表されるジニトロ化合物が得られる。下記一般式(2−a)で示される化合物と下記一般式(2−b)で示される化合物とは、同一であっても、異なっていてもよい。また、下記一般式(2−a)で示される化合物と下記一般式(2−b)で示される化合物のいずれか一方を、ニトロ基でなくアミノ基を有する化合物に替えて反応させることにより、式(1−c)及び(1−d)で表されるアミノ基及びニトロ基を有する化合物を得ることができる。
下記実施例において用いた測定方法及び装置は以下の通りである。
HPLC測定にはSHIMADZU製SPD−10Aを使用し、融点測定にはYAMATO製MP−21を使用した。
1H核磁気共鳴スペクトル分析には、JEOL製JNM−ECA600型を用い、共鳴周波数600MHzで測定した。測定溶媒は重クロロホルムを用いた。
13C核磁気共鳴スペクトル分析には、JEOL製JNM−ECA600型を用い、共鳴周波数150MHzで測定した。測定溶媒は重クロロホルムを用いた。
質量分析には、エーエムアールのDART/SVPを装着したSHIMADZU製のLCMS−2020を使用した。
1,4−ビス{2−[4−(3−メチル−4−ニトロフェノキシ)フェニル]−2−プロピル}ベンゼンの合成
該実施例1で製造した化合物の1H−NMRスペクトルのチャートを図1に示し、13C−NMRスペクトルのチャートを図2に示す。DART−MSの結果は以下の通り。
DART−MS:m/z=617(M+H)+,634(M+NH4)+
1,4−ビス{2−[4−(4−アミノ−3−メチルフェノキシ)フェニル]−2−プロピル}ベンゼンの合成
該実施例2で製造した化合物の1H−NMRスペクトルのチャートを図3に示し、13C−NMRスペクトルのチャートを図4に示す。
DART−MSの結果は以下の通り。
DART−MS:m/z=557(M+H)+
1,3−ビス{2−[4−(3−メチル―4−ニトロフェノキシ)フェニル]−2−プロピル}ベンゼンの合成
該実施例3で製造した化合物の1H−NMRスペクトルのチャートを図5に示し、13C−NMRスペクトルのチャートを図6に示す。DART−MSの結果は以下の通り。
DART−MS:m/z=617(M+H)+,634(M+NH4)+
1,3−ビス{2−[4−(4−アミノ−3−メチルフェノキシ)フェニル]−2−プロピル}ベンゼンの合成
該実施例4で製造した化合物の1H−NMRスペクトルのチャートを図7に示し、13C−NMRスペクトルのチャートを図8に示す。
DART−MSの結果は以下の通り。
DART−MS:m/z=557(M+H)+
1,4−ビス{2−[4−(2−メチル−4−ニトロフェノキシ)フェニル]−2−プロピル}ベンゼンの合成
該実施例5で製造した化合物の1H−NMRスペクトルのチャートを図9に示し、13C−NMRスペクトルのチャートを図10に示す。DART−MSの結果は以下の通り。
DART−MS:m/z=617(M+H)+,634(M+NH4)+
1,4−ビス{2−[4−(4−アミノ−2−メチルフェノキシ)フェニル]−2−プロピル}ベンゼンの合成
該実施例6で製造した化合物の1H−NMRスペクトルのチャートを図11に示し、13C−NMRスペクトルのチャートを図12に示す。
DART−MSの結果は以下の通り。
DART−MS:m/z=557(M+H)+
1,4−ビス[4−(2−メチル―4−ニトロフェノキシ)フェノキシ]ベンゼンの合成
該実施例7で製造した化合物の1H−NMRスペクトルのチャートを図13に示し、13C−NMRスペクトルのチャートを図14に示す。DART−MSの結果は以下の通り。
DART−MS:m/z=565(M+H)+
1,4−ビス[4−(4−アミノ−2−メチルフェノキシ)フェノキシ]ベンゼンの合成
該実施例8で製造した化合物の1H−NMRスペクトルのチャートを図15に示し、13C−NMRスペクトルのチャートを図16に示す。
DART−MSの結果は以下の通り。
DART−MS:m/z=505(M+H)+
Claims (17)
- 上記式(f)又は(f’)において、R21,R22、R23及びR24がメチル基である、請求項2又は3記載の化合物。
- 下記式(1−a)で表される化合物の製造方法であって
下記式(1−b)、式(1−c)又は式(1−d)で表される化合物のニトロ基を還元して上記式(1−a)で表される化合物を得る工程を含む、前記製造方法
- 下記式(1−b)で表される化合物の製造方法であって
下記式(2−a)で表される化合物及び下記式(2−b)で表される化合物の1以上と
(式中、R1、R2、R3、R4、R17、R18、R19及びR20は上記の通りであり、Yはハロゲン原子である)、
下記式(3−a)で表される化合物の1以上とを
反応させて上記式(1−b)で表される化合物を得る工程を含む、前記製造方法。 - 下記式(1−b)で表される化合物の製造方法であって
下記式(4−a)で表される化合物及び下記式(4−b)で表される化合物の1以上と
下記式(3−b)で表される化合物の1以上とを
反応させて上記式(1−b)で表される化合物を得る工程を含む、前記製造方法。 - 下記式(h)で表される化合物の製造方法であって
下記式(5−a)で表される化合物及び下記式(5−b)で表される化合物の1以上と
下記式(6−a)で表される化合物の1以上とを
反応させて上記式(h)で表される化合物を得る工程を含む、前記製造方法。 - 下記式(h)で表される化合物の製造方法であって
下記式(7−a)で表される化合物及び下記式(7−b)で表される化合物の1以上と
下記式(8−a)で表される化合物の1以上とを
反応させて上記式(h)で表される化合物を得る工程を含む、前記製造方法。 - Xが、酸素原子、単結合、又は、−CR21R22−及び−CR23R24−で表される二価炭化水素基であり、R21,R22、R23及びR24は、互いに独立に、水素原子、炭素数1〜6のアルキル基である、請求項5〜7のいずれか1項記載の製造方法。
- Xが−CR21R22−及び−CR23R24−で表され、R21,R22、R23及びR24がメチル基である、請求項10記載の製造方法。
- A及びBが共にアミノ基である、請求項1〜4のいずれか1項記載の化合物。
- 請求項12に記載の化合物と酸無水物との反応物である、ポリイミド化合物。
- 前記酸無水物が、ピロメリット酸二無水物、3,3’,4,4’−ビフェニルテトラカルボン酸二無水物、ベンゾフェノン−3,4,3’,4’−テトラカルボン酸二無水物、4,4’−(2,2−ヘキサフルオロイソプロピリデン)ジフタル酸二無水物、2,2−ビス〔3−(3,4−ジカルボキシフェノキシ)フェニル〕プロパン二無水物、2,2−ビス〔4−(3,4−ジカルボキシフェノキシ)フェニル〕プロパン二無水物、3,3’,4,4’−ジフェニルスルホンテトラカルボン酸二無水物およびオキシ−4,4’−ジフタル酸二無水物からなる群から選択される少なくとも1である、請求項13記載のポリイミド化合物。
- 数平均分子量2,000〜200,000を有する、請求項13または14に記載のポリイミド化合物。
- 請求項12記載の化合物と、酸無水物と、請求項12記載の化合物以外のジアミン化合物との反応物であるポリイミド化合物であって、請求項12記載の化合物に由来する単位と前記請求項11記載の化合物以外のジアミン化合物に由来する単位の合計モルに対する請求項12記載の化合物に由来する単位の割合が、10モル%〜100モル%である、請求項13〜15のいずれか1項記載のポリイミド化合物。
- 請求項13〜16のいずれか1項に記載のポリイミド化合物からなる成形物。
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2019065257A JP7345158B2 (ja) | 2019-03-29 | 2019-03-29 | 5つの芳香環を有するジアミノ又はジニトロベンゼン化合物、およびその製造方法、並びにポリイミド |
JP2023095707A JP2023126781A (ja) | 2019-03-29 | 2023-06-09 | 5つの芳香環を有するジアミノ又はジニトロベンゼン化合物、およびその製造方法、並びにポリイミド |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2019065257A JP7345158B2 (ja) | 2019-03-29 | 2019-03-29 | 5つの芳香環を有するジアミノ又はジニトロベンゼン化合物、およびその製造方法、並びにポリイミド |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2023095707A Division JP2023126781A (ja) | 2019-03-29 | 2023-06-09 | 5つの芳香環を有するジアミノ又はジニトロベンゼン化合物、およびその製造方法、並びにポリイミド |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2020164442A true JP2020164442A (ja) | 2020-10-08 |
JP7345158B2 JP7345158B2 (ja) | 2023-09-15 |
Family
ID=72717024
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2019065257A Active JP7345158B2 (ja) | 2019-03-29 | 2019-03-29 | 5つの芳香環を有するジアミノ又はジニトロベンゼン化合物、およびその製造方法、並びにポリイミド |
JP2023095707A Pending JP2023126781A (ja) | 2019-03-29 | 2023-06-09 | 5つの芳香環を有するジアミノ又はジニトロベンゼン化合物、およびその製造方法、並びにポリイミド |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2023095707A Pending JP2023126781A (ja) | 2019-03-29 | 2023-06-09 | 5つの芳香環を有するジアミノ又はジニトロベンゼン化合物、およびその製造方法、並びにポリイミド |
Country Status (1)
Country | Link |
---|---|
JP (2) | JP7345158B2 (ja) |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04178358A (ja) * | 1989-10-24 | 1992-06-25 | Mitsui Toatsu Chem Inc | 芳香族ジアミン化合物、ビスマレイミド化合物並びにこれらを用いた硬化性樹脂組成物及び樹脂並びにこれらの製造方法 |
JPH05310649A (ja) * | 1992-05-15 | 1993-11-22 | Mitsui Toatsu Chem Inc | 芳香族ジニトロ化合物、芳香族ジアミノ化合物及びそれらの製造方法 |
JPH06179816A (ja) * | 1992-04-02 | 1994-06-28 | Mitsui Toatsu Chem Inc | ポリイミド樹脂組成物 |
JPH08106097A (ja) * | 1994-10-06 | 1996-04-23 | Mitsui Toatsu Chem Inc | 液晶配向膜および液晶表示素子 |
JP2004002265A (ja) * | 2001-09-04 | 2004-01-08 | Mitsui Chemicals Inc | 新規な芳香族ジアミン及びその製造方法 |
WO2009045537A1 (en) * | 2007-10-04 | 2009-04-09 | Akron Polymer Systems | Poly(aryletherimides) for negative birefringent films for lcds |
CN106349923A (zh) * | 2016-08-26 | 2017-01-25 | 中国科学院上海硅酸盐研究所 | 一种含石墨烯的含氟聚酰亚胺复合耐腐蚀涂层的制备方法 |
WO2018062425A1 (ja) * | 2016-09-28 | 2018-04-05 | 日産化学工業株式会社 | 酸二無水物およびその利用 |
-
2019
- 2019-03-29 JP JP2019065257A patent/JP7345158B2/ja active Active
-
2023
- 2023-06-09 JP JP2023095707A patent/JP2023126781A/ja active Pending
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04178358A (ja) * | 1989-10-24 | 1992-06-25 | Mitsui Toatsu Chem Inc | 芳香族ジアミン化合物、ビスマレイミド化合物並びにこれらを用いた硬化性樹脂組成物及び樹脂並びにこれらの製造方法 |
JPH06179816A (ja) * | 1992-04-02 | 1994-06-28 | Mitsui Toatsu Chem Inc | ポリイミド樹脂組成物 |
JPH05310649A (ja) * | 1992-05-15 | 1993-11-22 | Mitsui Toatsu Chem Inc | 芳香族ジニトロ化合物、芳香族ジアミノ化合物及びそれらの製造方法 |
JPH08106097A (ja) * | 1994-10-06 | 1996-04-23 | Mitsui Toatsu Chem Inc | 液晶配向膜および液晶表示素子 |
JP2004002265A (ja) * | 2001-09-04 | 2004-01-08 | Mitsui Chemicals Inc | 新規な芳香族ジアミン及びその製造方法 |
WO2009045537A1 (en) * | 2007-10-04 | 2009-04-09 | Akron Polymer Systems | Poly(aryletherimides) for negative birefringent films for lcds |
CN106349923A (zh) * | 2016-08-26 | 2017-01-25 | 中国科学院上海硅酸盐研究所 | 一种含石墨烯的含氟聚酰亚胺复合耐腐蚀涂层的制备方法 |
WO2018062425A1 (ja) * | 2016-09-28 | 2018-04-05 | 日産化学工業株式会社 | 酸二無水物およびその利用 |
Non-Patent Citations (2)
Title |
---|
YANG, CHIN-PING ET AL.: "Light-color soluble polyimides based on α,α'-bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]-1,3-d", POLYMER JOURNAL(TOKYO, JAPAN), vol. 38, no. 5, JPN6022023635, 2006, pages 457 - 470, ISSN: 0004986147 * |
YANG, PENGFEI; MOLONEY, MARK G.: "Surface modification of polymers with bis(arylcarbene)s from bis(aryldiazomethane)s: preparation, dy", RSC ADVANCES, vol. 6, no. 112, JPN6022023633, 2016, pages 111276 - 111290, XP055420643, ISSN: 0004986148, DOI: 10.1039/C6RA24392D * |
Also Published As
Publication number | Publication date |
---|---|
JP7345158B2 (ja) | 2023-09-15 |
JP2023126781A (ja) | 2023-09-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Yan et al. | Soluble polyimides based on a novel pyridine-containing diamine m, p-PAPP and various aromatic dianhydrides | |
EP2940015A1 (en) | Novel polyamideimide having low thermal expansion coefficient | |
Sadavarte et al. | Regularly alternating poly (amideimide) s containing pendent pentadecyl chains: Synthesis and characterization | |
US6277950B1 (en) | Organic-soluble aromatic polyimides, organic solutions and preparation thereof | |
Sheng et al. | Synthesis and properties of novel aromatic polyamides with xanthene cardo groups | |
Qian et al. | Polyimides with low coefficient of thermal expansion derived from diamines containing benzimidazole and amide: Synthesis, properties, and the N‐substitution effect | |
JP5546210B2 (ja) | 芳香族ジアミン化合物及びその製造方法並びに合成樹脂 | |
WO2022239534A1 (ja) | メタ型エステル系芳香族ジアミン、およびその製造方法、並びにそれらのメタ型エステル系芳香族ジアミンを原料とするポリイミド | |
EP0387106B1 (en) | Novel diamine compounds, production of the same and polyamideimide resins produced therefrom | |
JP7345158B2 (ja) | 5つの芳香環を有するジアミノ又はジニトロベンゼン化合物、およびその製造方法、並びにポリイミド | |
JP7390754B2 (ja) | ビス(アミノ又はニトロフェノキシ)ベンゼン化合物、およびその製造方法、並びにポリイミド | |
Hsiao et al. | A novel class of organosoluble and light-colored fluorinated polyamides derived from 2, 2′-bis (4-amino-2-trifluoromethylphenoxy) biphenyl or 2, 2′-bis (4-amino-2-trifluoromethylphenoxy)-1, 1′-binaphthyl | |
JP7150335B2 (ja) | 4つの芳香環を有するジアミノ又はジニトロベンゼン化合物、およびその製造方法、並びにポリイミド | |
WO2006085493A1 (ja) | 芳香族ジアミン及びその製造方法 | |
Ghaemy et al. | Organosoluble and thermally stable polyimides derived from a new diamine containing bulky-flexible triaryl pyridine pendent group | |
JP2007297319A (ja) | 1,3−ビス(アミノフェノキシ)−5−(フェニルエチニル)ベンゼン誘導体およびその製造方法 | |
Rafiee et al. | Synthesis and characterization of highly soluble and thermally stable new polyimides based on 3, 5-diamino benzoyl amino phenyl-14H-dibenzo [a, j] xanthene | |
Ghaemy et al. | Synthesis of soluble and thermally stable polyamides from diamine containing (quinolin‐8‐yloxy) aniline pendant group | |
US5844065A (en) | 2,2'-dimethyl-4,4'-bis (4-aminophenoxy) biphenyl, and polymers prepared therefrom by polycondensation | |
US5177179A (en) | Perfluoroalkylated diaminomesitylene and polyimides therefrom | |
JP2009067936A (ja) | ポリアミック酸及びイミド化重合体 | |
JPH10298150A (ja) | 芳香族ジアミン化合物 | |
Ghaemy et al. | Synthesis of organosoluble polyamides with bulky triaryl imidazole pendent group | |
Behniafar et al. | Preparation and properties of aromatic poly (amide-imide) s derived from N-[3, 5-bis (3, 4-dicarboxybenzamido) phenyl] phthalimide dianhydride | |
US7317110B2 (en) | Low dielectric constant organo-soluble polyimides |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20211020 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20220614 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20220616 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20220809 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20221012 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20221223 |
|
RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20221223 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20230209 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20230405 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20230609 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20230808 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20230829 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 7345158 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |