JPH02115149A - 芳香族ジアミン化合物及びその製造方法 - Google Patents
芳香族ジアミン化合物及びその製造方法Info
- Publication number
- JPH02115149A JPH02115149A JP26730088A JP26730088A JPH02115149A JP H02115149 A JPH02115149 A JP H02115149A JP 26730088 A JP26730088 A JP 26730088A JP 26730088 A JP26730088 A JP 26730088A JP H02115149 A JPH02115149 A JP H02115149A
- Authority
- JP
- Japan
- Prior art keywords
- aromatic diamine
- diamine compound
- reaction
- manufacturing
- formula
- 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 Aromatic diamine compound Chemical class 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- JLZUZNKTTIRERF-UHFFFAOYSA-N tetraphenylethylene Chemical group C1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 JLZUZNKTTIRERF-UHFFFAOYSA-N 0.000 claims description 7
- 238000006396 nitration reaction Methods 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 229920006015 heat resistant resin Polymers 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000004984 aromatic diamines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 239000012770 industrial material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- MVFJHAFRIJSPFI-UHFFFAOYSA-N 3-(3,4,5-triphenylthiophen-2-yl)benzene-1,2-diamine Chemical compound NC=1C(=C(C=CC=1)C=1SC(=C(C=1C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)N MVFJHAFRIJSPFI-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 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
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- DBJUEJCZPKMDPA-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O DBJUEJCZPKMDPA-UHFFFAOYSA-N 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- OPTDDWCXQQYKGU-UHFFFAOYSA-N diphenyldichloromethane Chemical compound C=1C=CC=CC=1C(Cl)(Cl)C1=CC=CC=C1 OPTDDWCXQQYKGU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-N iron;hydrochloride Chemical compound Cl.[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- JOQGJRQKCIJIDB-UHFFFAOYSA-N tin;hydrochloride Chemical compound Cl.[Sn] JOQGJRQKCIJIDB-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26730088A JPH02115149A (ja) | 1988-10-25 | 1988-10-25 | 芳香族ジアミン化合物及びその製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26730088A JPH02115149A (ja) | 1988-10-25 | 1988-10-25 | 芳香族ジアミン化合物及びその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02115149A true JPH02115149A (ja) | 1990-04-27 |
| JPH0529392B2 JPH0529392B2 (enrdf_load_stackoverflow) | 1993-04-30 |
Family
ID=17442914
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26730088A Granted JPH02115149A (ja) | 1988-10-25 | 1988-10-25 | 芳香族ジアミン化合物及びその製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02115149A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104003886A (zh) * | 2013-02-25 | 2014-08-27 | 北京师范大学 | 多硝基取代四苯基乙烯化合物的制备及其应用 |
| CN113461546A (zh) * | 2021-07-27 | 2021-10-01 | 华中科技大学 | 一种发射深蓝色荧光的位阻型四苯乙烯螺旋体及合成方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6483054A (en) * | 1987-09-24 | 1989-03-28 | Toshiba Corp | Production of stilbene derivative |
-
1988
- 1988-10-25 JP JP26730088A patent/JPH02115149A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6483054A (en) * | 1987-09-24 | 1989-03-28 | Toshiba Corp | Production of stilbene derivative |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104003886A (zh) * | 2013-02-25 | 2014-08-27 | 北京师范大学 | 多硝基取代四苯基乙烯化合物的制备及其应用 |
| CN113461546A (zh) * | 2021-07-27 | 2021-10-01 | 华中科技大学 | 一种发射深蓝色荧光的位阻型四苯乙烯螺旋体及合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0529392B2 (enrdf_load_stackoverflow) | 1993-04-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Hilborn et al. | Poly (aryl ether-benzoxazoles) | |
| JPS59113034A (ja) | ポリアミド−イミドおよびその製造方法 | |
| JP6882737B2 (ja) | ベンゾオキサジン化合物、その製造方法及びベンゾオキサジン樹脂 | |
| US4973707A (en) | Acetylene bis-phthalic compounds and polyimides made therefrom | |
| JPH02115149A (ja) | 芳香族ジアミン化合物及びその製造方法 | |
| Ueda et al. | Synthesis of polyenamines by vinylogous nucleophilic substitution polymerization of 2, 2′‐disubstituted bis (4‐ethoxymethylene‐5‐oxazolone) with diamines | |
| US5739344A (en) | Preparation of an aminoarylaminoarazole | |
| US7282553B2 (en) | Flexible isopropylidene and tetramethyl-containing fluoropolyamide and fluoropolymide and preparation method thereof | |
| JP2718981B2 (ja) | 芳香族ジアミン化合物およびその製造方法 | |
| CN100387636C (zh) | 含脂环族侧基的聚二苯并噻唑-脲及其制备方法 | |
| JPH01115929A (ja) | ジアセチレン基を含有するポリアミドの製造方法 | |
| JPH066563B2 (ja) | 新規ジアミン化合物及びその製造法 | |
| US5245044A (en) | Di(hydroxyphenyl)-benzimidazole monomers | |
| CN1194968C (zh) | 一种含吡啶结构的芳香族四胺化合物及其制法和应用 | |
| JPH032170A (ja) | ジアミノ（フェニルベンツイミダゾール）の製造方法 | |
| JPH02160752A (ja) | ブタジイン系イミド | |
| SU785295A1 (ru) | Бензилоксиаценафтенхиноны в качестве мономеров дл полихиноксалинов, обладающих повышенной термостойкостью и растворимостью | |
| JPS61250029A (ja) | キノキサリン環を有するポリアミド樹脂及びその製造法 | |
| USH754H (en) | Arloxy p-phenylene diamines | |
| JP4016301B2 (ja) | 新規なアゾ基含有芳香族化合物及びその製造法 | |
| JP2540618B2 (ja) | 新規な芳香族ジアミン系化合物およびその製造方法 | |
| JP2005247697A (ja) | アミノアリルアミノベンザゾールの製造方法およびその誘導体 | |
| JP2009191014A (ja) | アミノアリルアミノアラゾールの製造方法 | |
| JPH0660143B2 (ja) | 新規ジアミン化合物及びその製造法 | |
| JPH01123832A (ja) | 芳香族ポリアミド−イミド樹脂の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313111 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| EXPY | Cancellation because of completion of term |