JPH01242584A - aromatic diamine - Google Patents
aromatic diamineInfo
- Publication number
- JPH01242584A JPH01242584A JP7072288A JP7072288A JPH01242584A JP H01242584 A JPH01242584 A JP H01242584A JP 7072288 A JP7072288 A JP 7072288A JP 7072288 A JP7072288 A JP 7072288A JP H01242584 A JPH01242584 A JP H01242584A
- Authority
- JP
- Japan
- Prior art keywords
- porphyrin
- diphenylporphyrin
- nitrobenzaldehyde
- tpp
- nitrophenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000004984 aromatic diamines Chemical class 0.000 title 1
- 150000004032 porphyrins Chemical group 0.000 claims abstract description 8
- 150000004985 diamines Chemical class 0.000 claims abstract description 7
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract description 6
- 239000004642 Polyimide Substances 0.000 abstract description 3
- -1 dinitro compound Chemical class 0.000 abstract description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract description 3
- 229920002312 polyamide-imide Polymers 0.000 abstract description 3
- 229920001721 polyimide Polymers 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 abstract description 2
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004952 Polyamide Substances 0.000 abstract description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 2
- 229920002647 polyamide Polymers 0.000 abstract 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 abstract 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 abstract 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 abstract 1
- 235000011150 stannous chloride Nutrition 0.000 abstract 1
- 239000001119 stannous chloride Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000009102 absorption Effects 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004962 Polyamide-imide Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FIDQDDFTUULQAU-UHFFFAOYSA-N 21,23-diphenylporphyrin Chemical compound C1(=CC=CC=C1)N1C=2C=CC1=CC=1C=CC(=CC3=CC=C(N3C3=CC=CC=C3)C=C3C=CC(C2)=N3)N1 FIDQDDFTUULQAU-UHFFFAOYSA-N 0.000 description 1
- JCLFHZLOKITRCE-UHFFFAOYSA-N 4-pentoxyphenol Chemical compound CCCCCOC1=CC=C(O)C=C1 JCLFHZLOKITRCE-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical compound C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、ポルフィリン環含有ジアミンに関する。[Detailed description of the invention] [Industrial application field] The present invention relates to a porphyrin ring-containing diamine.
本発明のジアミンは、ポリイミドやポリアミドイミド等
の原料として有用である。The diamine of the present invention is useful as a raw material for polyimide, polyamideimide, and the like.
本発明は、下記構造式〔Ｉ〕または〔ＩＩ〕で表わされ
るポルフィリン環含有ジアミンである。The present invention is a porphyrin ring-containing diamine represented by the following structural formula [I] or [II].
本発明のポルフィリン環含有ジアミンは、具体的には以
下に示す構造を有する化合物である。Specifically, the porphyrin ring-containing diamine of the present invention is a compound having the structure shown below.
Ｈ２
これらの化合物は、例えば、先ずｐ−ニトロベンツアル
デヒド又はｍ−ニトロベンツアルデヒドとベンツアルデ
ヒドを含む溶液中にピロールを滴下し、還流することに
より、相当するジニトロ化合物を得、次いでニトロ基を
塩化第一スズ等で還元して、ジ（アミノフェニル）ジフ
ェニルポルフィリンを得ることが出来る。H2 These compounds can be obtained, for example, by first dropping pyrrole into a solution containing p-nitrobenzaldehyde or m-nitrobenzaldehyde and benzaldehyde and refluxing to obtain the corresponding dinitro compound, and then chlorinating the nitro group. Di(aminophenyl)diphenylporphyrin can be obtained by reduction with stannous or the like.
本発明のジアミンは力学的、熱的、化学的に安定で新規
な機能を有する、ポルフィリン含有ポリイミド、ポリア
ミドイミド、ポリアミドなどの原料として使用すること
ができる。The diamine of the present invention is mechanically, thermally, and chemically stable and has novel functions, and can be used as a raw material for porphyrin-containing polyimide, polyamideimide, polyamide, and the like.
実施例／
イ）ｊ、／＆−ジ（ｌＩ−ニトロフェニル）１０゜、２
０−ジフェニルポルフィリンＣｔ−ジニトロＴｐｐ ）
の合成
２１の三つロフラスコに、還流冷却器、滴下ロート、シ
ール付キメカニカルスターラーを取り付け、ｐ−二トロ
ペンツアルデヒド／ ９．７ ｇ（Ｏ，／ 、？ｍｏｌ
）とベンツアルデヒド／ ３．Ａ ｇ（０，／ 、？ｍ
ｏｌ ）を取り、プロピオン酸９７５ｍ１を加えた。こ
の懸濁液にピロールを／ ７．ｑｇ（０，７Ａｍｏｌ）
をゆっくり滴下し、マントルヒーターで加熱し、３０分
還流した。Example/a) j, /&-di(lI-nitrophenyl) 10°, 2
0-diphenylporphyrin Ct-dinitroTpp)
Synthesis 21 A three-necked flask was equipped with a reflux condenser, a dropping funnel, and a mechanical stirrer with a seal.
) and benzaldehyde/3. A g(0, / ,?m
ol) was taken, and 975 ml of propionic acid was added. Add pyrrole to this suspension/7. qg (0,7 Amol)
was slowly added dropwise, heated with a mantle heater, and refluxed for 30 minutes.
反応液は黒色であり、これから減圧下でプロピオン酸を
蒸発させ残存物の黒色固体をクロロホルムでソックスレ
ー抽出器により抽出し、可溶分だけを取り出し、それを
塩化メチレンで高速カラムクロマト（ワコーゲルＣ３０
０）にかけ、流出分だけを取り出した。この流出液には
、テトラフェニルポルフィリン（ｒｐｐ）、５−（ｌＩ
−ニトロフェニル）−７０，／ｌ ２０−トリフェニル
ポルフィリン（モノニトロＴｐｐ ）、３． ／ ！−
ジ（＋−ニトロフェニル）−１０，２０−ジフェニルポ
ルフィリン（ｔ−ジニトロＴｐｐ ）、！；、１０−ジ
（ｌＩ−ニトロフェニル） −ｙｓ、２ｏ ＝ジフェニ
ルポルフィリン（Ｃ−ジニトロＴｐｐ ）、ｊｔ、１０
．／Ｓ−トリ（ｌＩ−ニトロフェニル）−２０−フェニ
ルポルフィリン（トリニトロＴｐｐ）、ｊｔ１０、／！
；、、２０−テトラ（ダーニトロフェニル）ポルフィリ
ン（テトラニトロＴｐｐ ）などが含まれているので、
溶媒として、塩化メチレン−ヘキサン（Ａ＆：ｊ５）を
用いカラムクロマト（ワコーゲルＣ−３００）で分離精
製した。The reaction solution was black, and propionic acid was evaporated from it under reduced pressure, and the remaining black solid was extracted with chloroform using a Soxhlet extractor.
0) and only the effluent was taken out. This effluent contains tetraphenylporphyrin (rpp), 5-(lI
-nitrophenyl)-70,/l 20-triphenylporphyrin (mononitroTpp), 3. /! −
Di(+-nitrophenyl)-10,20-diphenylporphyrin (t-dinitroTpp),! ;, 10-di(lI-nitrophenyl)-ys, 2o = diphenylporphyrin (C-dinitroTpp), jt, 10
．． /S-tri(lI-nitrophenyl)-20-phenylporphyrin (trinitroTpp), jt10, /!
It contains 20-tetra(dernitrophenyl)porphyrin (tetranitroTpp), etc.
Separation and purification was performed using column chromatography (Wakogel C-300) using methylene chloride-hexane (A&:j5) as a solvent.
それぞれのポルフィリンについて薄層クロマトグラフィ
ー（シリカプレート（Ｋｉｅｓｅ１ｇｅｌ／、０Ｔ−２
！；ＩＩ））及び液体クロマトグラフィーを行い、その
ＲＴ及びＲｆを下表に示す。Thin layer chromatography (silica plate (Kiesel gel/, 0T-2
! ;II)) and liquid chromatography were performed, and the RT and Rf are shown in the table below.
２−′
なお、′トリニトロＴｐｐとテトラニトロＴｐｐは単離
しなかった。またｔ−ジニトロＴｐｐとＣ−ジニトロＴ
ｐｐは分離できなかった。2-' Note that 'trinitro Tpp and tetranitro Tpp were not isolated. Also, t-dinitroTpp and C-dinitroT
pp could not be separated.
口）ｓ、ｉｓ−ジ（グーアミノフェニル）−ジフェニル
ポルフィリン（１−ジアミノＴｐｐ）の合成
／２の三つロフラスコに、還流冷却器、マグネチックス
ターラーを取りつけ、この容器内で、ジ（グーアミノフ
ェニル）−ジフェニルポルフィリンｑ、’／ ２ ！ｒ
７ ｆｉ （！、Ｋ ｊｍｍｏｌ ）を！；００ｍ１
の酢酸エチルに溶解し、これに塩化第一スズニ水物２６
．ｌＩｇと、６規定の塩酸ＡｇｒｒＬｌを加え、窒素雰
囲気下、ざ０℃でｇ時間環流した。その後反応液を炭酸
水素ナトリウムで中和し、分液ロートで酢酸エチル相を
取り出し、その液を塩化す） ＩＪウム溶液で洗い、再
び酢酸エチル相をとり出し、無水硫駿ナトリウムで脱水
し、酢酸エチルを蒸発させ、ｔ−ジアミノＴｐｐとＣ−
ジアミノＴｐｐの混合物を得た。これを塩化メチレン−
酢酸エチル（／９二／）の溶媒でカラムクロマト分離し
、クロロホルムに溶解し、ｎ−ヘキサンを少しずつ加え
て再結晶して精製した。Synthesis of s,is-di(guaminophenyl)-diphenylporphyrin (1-diaminoTpp)/A reflux condenser and a magnetic stirrer were attached to the 2 three-necked flask, and in this container, di(guaminophenyl)-diphenylporphyrin (1-diamino Tpp) was prepared. phenyl)-diphenylporphyrin q,'/2! r
7 fi (!, K jmmol)! ;00m1
Dissolved in ethyl acetate, to which stannous chloride hydrate 26
．． 1Ig and 6N hydrochloric acid AgrrLl were added, and the mixture was refluxed at 0° C. for g hours under a nitrogen atmosphere. Thereafter, the reaction solution was neutralized with sodium hydrogen carbonate, the ethyl acetate phase was taken out using a separatory funnel, and the liquid was chlorinated.) Washed with an IJium solution, the ethyl acetate phase was taken out again, and dehydrated with anhydrous sodium sulfate. Ethyl acetate was evaporated and t-diamino Tpp and C-
A mixture of diamino Tpp was obtained. This is methylene chloride
The product was purified by column chromatography using ethyl acetate (/92/), dissolved in chloroform, and recrystallized by adding n-hexane little by little.
それぞれのシリカゲルプレートのＲＴを下表に示す。The RT of each silica gel plate is shown in the table below.
それぞれの元素分析値を下表に示す。The elemental analysis values for each are shown in the table below.
それぞれの赤外吸収スペクトルの吸収ピーク値（ｃＩＩ
Ｌ−’）を下表に示す。The absorption peak value of each infrared absorption spectrum (cII
L-') is shown in the table below.
Ｈｌ−ＮＭＲスペクトルの結果を下表に示す（溶媒ニジ
メチルスルホキシドＤ、 ）。The results of the Hl-NMR spectrum are shown in the table below (solvent dimethyl sulfoxide D, ).
７．０ ケ
襄６ ４（−ＮＨ２）
Ｃ−ジアミノＴｐｐ
ｔ−ジアミノＴｐｐとＣ−ジアミノＴｐｐの同定は、Ｎ
ＭＲスペクトルのδキ９に現われるビロール環のＨａと
Ｈｂに基ずく吸収の相違で行った。両吸収が、対称的な
ダブレットを示すものをｔ−ジアミノＴｐｐとし、それ
ぞれが二組のダブレットを示すものをＣ−ジアミノＴｐ
ｐとした。7.0 6 4(-NH2) C-diamino Tpp The identification of t-diamino Tpp and C-diamino Tpp is N
This was done based on the difference in absorption based on Ha and Hb of the virole ring that appears at δ-9 in the MR spectrum. A case where both absorptions show a symmetrical doublet is called t-diamino Tpp, and a case where each absorption shows two sets of doublets is called C-diamino Tp.
p.
Claims (1)
フィリン環含有ジアミン。 ▲数式、化学式、表等があります▼・・・・・・・・・
・・・〔 I 〕 ▲数式、化学式、表等があります▼・・・・・・・・・
・・・〔II〕[Scope of Claims] 1) A porphyrin ring-containing diamine represented by the following structural formula [I] or [II]. ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・・・・
・・・〔I〕 ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・・・・
...[II]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7072288A JPH01242584A (en) | 1988-03-24 | 1988-03-24 | aromatic diamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7072288A JPH01242584A (en) | 1988-03-24 | 1988-03-24 | aromatic diamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01242584A true JPH01242584A (en) | 1989-09-27 |
Family
ID=13439732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7072288A Pending JPH01242584A (en) | 1988-03-24 | 1988-03-24 | aromatic diamine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01242584A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104865292A (en) * | 2015-04-27 | 2015-08-26 | 济南大学 | Nitrogen dioxide gas sensor based on o-aminophenyl substituted porphyrin nanometer material |
| CN116903860A (en) * | 2023-08-18 | 2023-10-20 | 中科认证技术服务(广州)有限公司 | Polyimide-loaded triaminoporphyrin probe, preparation method thereof and application thereof in detection of nitroaromatic explosives |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58213778A (en) * | 1982-06-08 | 1983-12-12 | Hidetoshi Tsuchida | Iron-tetraphenylporphyrin complex having carboxyl group |
| JPS6051191A (en) * | 1983-06-03 | 1985-03-22 | エフ・ホフマン−ラ ロシユ ウント コンパニ− アクチエンゲゼルシヤフト | Porphylin derivative |
| JPS61130220A (en) * | 1984-11-26 | 1986-06-18 | エフアモル・リミテツド | Manufacture of antitumoral drug |
-
1988
- 1988-03-24 JP JP7072288A patent/JPH01242584A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58213778A (en) * | 1982-06-08 | 1983-12-12 | Hidetoshi Tsuchida | Iron-tetraphenylporphyrin complex having carboxyl group |
| JPS6051191A (en) * | 1983-06-03 | 1985-03-22 | エフ・ホフマン−ラ ロシユ ウント コンパニ− アクチエンゲゼルシヤフト | Porphylin derivative |
| JPS61130220A (en) * | 1984-11-26 | 1986-06-18 | エフアモル・リミテツド | Manufacture of antitumoral drug |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104865292A (en) * | 2015-04-27 | 2015-08-26 | 济南大学 | Nitrogen dioxide gas sensor based on o-aminophenyl substituted porphyrin nanometer material |
| CN116903860A (en) * | 2023-08-18 | 2023-10-20 | 中科认证技术服务(广州)有限公司 | Polyimide-loaded triaminoporphyrin probe, preparation method thereof and application thereof in detection of nitroaromatic explosives |
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