JPH0651791B2 - Optically active polyamide - Google Patents
Optically active polyamideInfo
- Publication number
- JPH0651791B2 JPH0651791B2 JP60019764A JP1976485A JPH0651791B2 JP H0651791 B2 JPH0651791 B2 JP H0651791B2 JP 60019764 A JP60019764 A JP 60019764A JP 1976485 A JP1976485 A JP 1976485A JP H0651791 B2 JPH0651791 B2 JP H0651791B2
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- present
- polyamide
- active polyamide
- head
- 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
Landscapes
- Pyrrole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Polyamides (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は光学活性アンチ頭−頭クマリン二量体の誘導体
に相当する新規な光学活性ポリアミドに関する。TECHNICAL FIELD The present invention relates to a novel optically active polyamide corresponding to a derivative of an optically active anti-head-head coumarin dimer.
クマリンを光二量化することによりアンチ頭−頭クマリ
ン二量体が得られる。An anti-head-to-head coumarin dimer is obtained by photodimerizing coumarin.
この物質は下記二種の光学異性体の混合物であり光学的
に不活性である。This substance is a mixture of the following two optical isomers and is optically inactive.
このラセミ体は本発明者らの発明した方法により光学活
性アミンとの反応で得られるジアステレオジアミドの溶
解性の差を利用して分解される。 This racemate is decomposed by utilizing the difference in solubility of diastereodiamide obtained by the reaction with the optically active amine by the method invented by the present inventors.
本発明者等は、このようにして得られた光学活性体
〔（＋）及び（−）二量体〕を不斉炭素を有するジアミ
ノ化合物と反応させることにより新規な光学活性ポリマ
ーが得られることを発見し、本発明に至った。The inventors of the present invention can obtain a novel optically active polymer by reacting the thus obtained optically active compound [(+) and (−) dimer] with a diamino compound having an asymmetric carbon. The present invention was discovered.
即ち、本発明は下記一般式（Ｉ）又は（II）で表わされ
る光学活性ポリアミドに係るものである。That is, the present invention relates to an optically active polyamide represented by the following general formula (I) or (II).
ここでＡは不斉炭素を有する第１又は第２ジアミンの２
個のアミノ基から１個づつの活性水素を除いた残基であ
る。かかるジアミンは飽和であってもよく又不飽和であ
ってもよい。又二種以上のジアミンの混合物であっても
よく、必要に応じ３価以上のアミンで変性してもよい。 Here, A is 2 of the first or second diamine having an asymmetric carbon.
It is a residue obtained by removing one active hydrogen from each amino group. Such diamines may be saturated or unsaturated. Further, it may be a mixture of two or more kinds of diamines, and may be modified with a trivalent or higher amine as required.
本発明の光学活性ポリアミドの原料となる不斉炭素を有
するジアミノ化合物の一例を下記に示す。An example of a diamino compound having an asymmetric carbon as a raw material of the optically active polyamide of the present invention is shown below.
これらの不斉炭素を有するジアミノ化合物は相当するジ
カルボン酸から の順で合成可能であり、上記の化合物に限定されるもの
ではない。 Diamino compounds having these asymmetric carbons are prepared from the corresponding dicarboxylic acid. Can be synthesized in this order, and is not limited to the above compounds.
本発明の光学活性ポリアミドの還元粘度は0.1〜0.7であ
る。The reduced viscosity of the optically active polyamide of the present invention is 0.1 to 0.7.
本発明の光学活性ポリアミドは（＋）又は（−）アンチ
頭−頭クマリン二量体と相当するジアミンとの反応によ
り容易に得られる。通常特別な触媒を必要としない。両
者の等モル量を非プロトン性極性溶媒中で反応させる方
法は好ましい方法である。非プロトン性極性溶媒として
はジメチルアセトアミド、ジオキサン、メチルピロリド
ン、ジメチルスルホキシド、ヘキサメチルホスホリック
トリアミド等が好ましい例である。The optically active polyamide of the present invention can be easily obtained by reacting a (+) or (-) anti-head-head coumarin dimer with a corresponding diamine. Usually no special catalyst is required. A method of reacting equimolar amounts of both in an aprotic polar solvent is a preferred method. Preferred examples of the aprotic polar solvent include dimethylacetamide, dioxane, methylpyrrolidone, dimethylsulfoxide, and hexamethylphosphoric triamide.
本発明の光学活性ポリアミドは、相当するラセミ体ポリ
アミドとは光学的性質の他、溶解性、熱的性質等も異な
る。The optically active polyamide of the present invention differs from the corresponding racemic polyamide in optical properties, solubility, thermal properties and the like.
本発明の光学活性ポリアミドは分子内に反応性の高いフ
ェノール基を有し、又光学活性がシクロブタン環に由来
する特徴を有するため、それ自体又はフェノールの誘導
体又は部分的にシクロブタン環を開裂された形で不斉合
成、光学分割分析等に有用な物質である。Since the optically active polyamide of the present invention has a highly reactive phenol group in the molecule and has a characteristic that the optical activity is derived from the cyclobutane ring, it is itself or a derivative of phenol or the cyclobutane ring is partially cleaved. In the form, it is a substance useful for asymmetric synthesis, optical resolution analysis, etc.
以下実施例にて本発明を説明する。 The present invention will be described below with reference to examples.
実施例１ （＋）アンチ頭−頭クマリン二量体1.0981g（3.76mmo
l）と当モル量の（＋）アニリノメチルピロリジン
（〔α〕▲19 D▼＋19.2゜（C1.19、エタノール中））と
をジメチルアセトアミド7.0ml中に溶解し、95℃で48時
間撹拌した。Example 1 (+) anti-head-head coumarin dimer 1.0981 g (3.76 mmo
l) and an equimolar amount of (+) anilinomethylpyrrolidine ([α] ▲ 19 D ▼ 19.2 ° (C1.19 in ethanol)) were dissolved in 7.0 ml of dimethylacetamide and the mixture was dissolved at 48 ° C at 95 ° C. Stir for hours.
反応終了後生成物をメタノール中に滴下することにより
ポリマーを得た（収率83％）。After the reaction was completed, the product was dropped into methanol to obtain a polymer (yield 83%).
還元粘度及び旋光度を表−１に示す。The reduced viscosity and the optical rotation are shown in Table-1.
実施例２ ジアミンとして（＋）トランススチルベンジアミン
（〔α〕▲14 D▼＋105.2゜（C1.00、メタノール中））
を用い、1.63mmolを3mlのジメチルアセトアミド中で実
施例１と同様に反応させ、ポリマーを得た（収率90
％）。As Example 2 diamine (+) trans-stilbene diamine ([α] ▲ 14 D ▼ + 105.2 ° (c 1.00, methanol))
Was used to react 1.63 mmol in 3 ml of dimethylacetamide in the same manner as in Example 1 to obtain a polymer (yield 90
%).
還元粘度及び旋光度を表−１に示す。The reduced viscosity and the optical rotation are shown in Table-1.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭58−55926（ＪＰ，Ａ) Ｊｏｕｒｎａｌ ｏｆ Ｐｏｌｙｍｅｒ ｓｃｉｅｎｃｅ，Ｐｏｌｙｍｅｒ Ｌｅ ｔｔｅｒｓ Ｅｄｉｔｉｏｎ，23［12 ］（1985）Ｐ．617−621 Ｊｏｕｒｎａｌ ｏｆ Ｐｏｌｙｍｅｒ ｓｃｉｅｎｃｅ，Ｐｏｌｙｍｅｒ Ｌｅ ｔｔｅｒｓ Ｅｄｉｔｉｏｎ，20［６ ］（1982）Ｐ．309−313 Ｊｏｕｒｎａｌ ｏｆ Ｐｏｌｙｍｅｒ ｓｃｉｅｎｃｅ，Ｐｏｌｙｍｅｒ Ｃｈ ｅｍｉｓｔｒｙ Ｅｄｉｔｉｏｎ，21［８ ］（1983）Ｐ．2345−2362 ─────────────────────────────────────────────────── --Continued front page (56) Reference JP-A-58-55926 (JP, A) Journal of Polymer science, Polymer Letters Edition, 23 [12] (1985) P. 617-621 Journal of Polymer science, Polymer Letters Edition, 20 [6] (1982) P. 309-313 Journal of Polymer science, Polymer Chemistry Edition, 21 [8] (1983) P. 2345-2362
Claims (1)
光学活性ポリアミド。 （但し、Ａは不斉炭素を有する第１又は第２ジアミンの
２個のアミノ基から１個づつの活性水素を除いた残基）1. An optically active polyamide represented by the following general formula (I) or (II). (However, A is a residue obtained by removing one active hydrogen from each of the two amino groups of the first or second diamine having an asymmetric carbon)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60019764A JPH0651791B2 (en) | 1985-02-04 | 1985-02-04 | Optically active polyamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60019764A JPH0651791B2 (en) | 1985-02-04 | 1985-02-04 | Optically active polyamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61179229A JPS61179229A (en) | 1986-08-11 |
| JPH0651791B2 true JPH0651791B2 (en) | 1994-07-06 |
Family
ID=12008403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60019764A Expired - Lifetime JPH0651791B2 (en) | 1985-02-04 | 1985-02-04 | Optically active polyamide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0651791B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102089711B (en) * | 2008-07-09 | 2013-05-22 | 日产化学工业株式会社 | Positive photosensitive resin composition and polyhydroxyamide resin |
-
1985
- 1985-02-04 JP JP60019764A patent/JPH0651791B2/en not_active Expired - Lifetime
Non-Patent Citations (3)
| Title |
|---|
| ＪｏｕｒｎａｌｏｆＰｏｌｙｍｅｒｓｃｉｅｎｃｅ，ＰｏｌｙｍｅｒＣｈｅｍｉｓｔｒｙＥｄｉｔｉｏｎ，２１［８（１９８３）Ｐ．２３４５−２３６２ |
| ＪｏｕｒｎａｌｏｆＰｏｌｙｍｅｒｓｃｉｅｎｃｅ，ＰｏｌｙｍｅｒＬｅｔｔｅｒｓＥｄｉｔｉｏｎ，２０［６（１９８２）Ｐ．３０９−３１３ |
| ＪｏｕｒｎａｌｏｆＰｏｌｙｍｅｒｓｃｉｅｎｃｅ，ＰｏｌｙｍｅｒＬｅｔｔｅｒｓＥｄｉｔｉｏｎ，２３［１２（１９８５）Ｐ．６１７−６２１ |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61179229A (en) | 1986-08-11 |
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