JPH0686496B2 - Method for producing novel conjugated polymer material by solid-state polymerization - Google Patents
Method for producing novel conjugated polymer material by solid-state polymerizationInfo
- Publication number
- JPH0686496B2 JPH0686496B2 JP3313643A JP31364391A JPH0686496B2 JP H0686496 B2 JPH0686496 B2 JP H0686496B2 JP 3313643 A JP3313643 A JP 3313643A JP 31364391 A JP31364391 A JP 31364391A JP H0686496 B2 JPH0686496 B2 JP H0686496B2
- Authority
- JP
- Japan
- Prior art keywords
- conjugated polymer
- polymer
- chemical
- rays
- polymer material
- 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
- 229920000547 conjugated polymer Polymers 0.000 title claims description 26
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 239000002861 polymer material Substances 0.000 title claims description 7
- 238000006116 polymerization reaction Methods 0.000 title description 12
- 239000000126 substance Substances 0.000 claims description 17
- 239000013078 crystal Substances 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 16
- 230000001678 irradiating effect Effects 0.000 claims description 5
- ZDDKBZSMUOQPAK-UHFFFAOYSA-N dodeca-1,3,5,7,9,11-hexayne Chemical class C#CC#CC#CC#CC#CC#C ZDDKBZSMUOQPAK-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 239000000463 material Substances 0.000 description 10
- 238000000921 elemental analysis Methods 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 6
- 239000007790 solid phase Substances 0.000 description 5
- 230000005251 gamma ray Effects 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 229920000015 polydiacetylene Polymers 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- PYJFQUAKQYTASA-UHFFFAOYSA-N CCCCOC(C=NC(O)=O)=O Chemical compound CCCCOC(C=NC(O)=O)=O PYJFQUAKQYTASA-UHFFFAOYSA-N 0.000 description 2
- 238000012644 addition polymerization Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 239000000696 magnetic material Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 238000012643 polycondensation polymerization Methods 0.000 description 2
- -1 polythienylene Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000010365 information processing Effects 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、新規な共役高分子材料
の製造方法、詳しくは、ドデカヘキサイン誘導体分子の
結晶から固相重合によりFIELD OF THE INVENTION The present invention relates to a method for producing a novel conjugated polymer material, more specifically, solid phase polymerization from crystals of dodecahexayne derivative molecules.
【化７】 で示される重合体からなる材料を製造する方法に関する
ものである。[Chemical 7] The present invention relates to a method for producing a material comprising a polymer represented by
【０００２】[0002]
【従来の技術】近年、電子材料、光材料、磁性材料等と
して、無機材料に比べ、分子修飾の容易さ、材料化法の
多様性等の長所を有する有機材料を用いることが広く検
討されている。特にポリジアセチレン、ポリアセチレ
ン、ポリチエニレン、ポリ（ｐ−フェニレンビニレン）
等の共役高分子は、導電性材料としての応用のみなら
ず、最近では、将来の光情報処理のための基幹材料とし
て注目される、３次の非線形光学材料としても期待され
ている。共役高分子を製造する方法としては、従来、溶
液中での触媒による付加重合、酸化試薬による縮合重
合、電気化学的に縮合させる電解重合、可溶性前駆体か
らの脱離による二重結合の生成、固相重合等が用いられ
てきた。2. Description of the Related Art Recently, as an electronic material, an optical material, a magnetic material, etc., it has been widely studied to use an organic material having advantages such as easiness of molecular modification and versatility of materialization method as compared with an inorganic material. There is. Especially polydiacetylene, polyacetylene, polythienylene, poly (p-phenylene vinylene)
The conjugated polymers such as are not only applied as a conductive material, but are also expected as a third-order nonlinear optical material, which is recently attracting attention as a basic material for future optical information processing. As a method for producing a conjugated polymer, conventionally, addition polymerization with a catalyst in a solution, condensation polymerization with an oxidizing reagent, electrolytic polymerization with electrochemical condensation, generation of a double bond by elimination from a soluble precursor, Solid state polymerization and the like have been used.
【０００３】[0003]
【発明が解決しようとする課題】従来用いられている共
役高分子の製造方法では次のような種々の課題点があっ
た。触媒による付加重合、酸化試薬による縮合重合、電
気化学的に縮合させる電解重合、可溶性前駆体からの脱
離による二重結合の生成等では、共役高分子の生成ある
いはその前駆体の生成の段階で溶媒を用いている。これ
らの製造方法では溶媒中で高分子が生成し、高分子化に
伴う溶解度の減少によって、生成した重合体が凝集して
沈澱するが、このようにして得られた重合体は、その高
分子鎖の配向が無秩序である。種々の機能発現に直接寄
与している部分は共役高分子鎖であるため、それらから
なる材料の性能向上という観点からみると、共役高分子
の主鎖は一方向にそろっている方が望ましく、溶媒を用
いた重合は適切ではない。一方、固相重合では、単量体
の結晶構造をそのまま受け継いで重合が進行するため、
共役高分子鎖の配向をそろえることが可能である。しか
しながら、この方法で得られる共役高分子としては、ポ
リジアセチレンに限られており、さらなる性能向上を目
指した新規な共役高分子化合物への展開はなされていな
かった。上述のように従来法では種々の課題点があるた
め、新規な共役高分子からなり、しかも、共役高分子鎖
が一方向にそろった材料の製造方法の開発は、現在最も
要求されているところである。The conventional methods for producing conjugated polymers have various problems as described below. In addition polymerization with a catalyst, condensation polymerization with an oxidizing reagent, electrolytic polymerization with electrochemical condensation, formation of double bond by elimination from a soluble precursor, etc., at the stage of formation of a conjugated polymer or its precursor. A solvent is used. In these production methods, a polymer is produced in a solvent, and the polymer is aggregated and precipitated due to the decrease in solubility accompanying the polymerization. The orientation of the chains is disordered. Since the part that directly contributes to the expression of various functions is the conjugated polymer chain, from the viewpoint of improving the performance of the material composed of them, it is desirable that the main chains of the conjugated polymer are aligned in one direction, Polymerization with solvents is not suitable. On the other hand, in solid phase polymerization, the polymerization proceeds by inheriting the crystal structure of the monomer as it is,
It is possible to align the orientation of the conjugated polymer chains. However, the conjugated polymer obtained by this method is limited to polydiacetylene, and it has not been developed to a novel conjugated polymer compound aiming at further improvement in performance. Since there are various problems in the conventional method as described above, the development of a method for producing a material composed of a novel conjugated polymer, in which the conjugated polymer chains are aligned in one direction, is currently most demanded. is there.
【０００４】[0004]
【課題を解決するための手段】本発明者は、高分子鎖の
配向が一方向に制御された共役高分子材料を得ることが
可能な固相重合法を用い、しかも、新規な共役高分子を
製造する方法を見い出すべく種々検討を重ねた結果、本
発明に到達したものである。即ち、本発明は、新規な共
役高分子材料の製造方法、詳しくは、ドデカヘキサイン
誘導体分子の結晶から固相重合により、従来全く知られ
ていなかった共役高分子構造を有するThe present inventor uses a solid phase polymerization method capable of obtaining a conjugated polymer material in which the orientation of polymer chains is controlled in one direction, and a novel conjugated polymer is used. The present invention has been achieved as a result of various studies to find a method for manufacturing That is, the present invention has a method for producing a novel conjugated polymer material, specifically, a conjugated polymer structure which has not been known at all by solid phase polymerization from crystals of dodecahexayne derivative molecules.
【化８】 で示される重合体からなる材料を製造する方法に関する
ものである。[Chemical 8] The present invention relates to a method for producing a material comprising a polymer represented by
【０００５】[0005]
【作用】本発明において最も重要な点は、新規な共役高
分子の合成において固相重合法を用いることにより、材
料中の共役高分子鎖の配向を一方向にそろえることが可
能であり、しかも、電子材料、光材料、磁性材料等とし
て期待される共役高分子であるThe most important point in the present invention is that it is possible to align the orientation of the conjugated polymer chains in the material in one direction by using the solid phase polymerization method in the synthesis of the novel conjugated polymer. , A conjugated polymer expected as electronic materials, optical materials, magnetic materials, etc.
【化９】 で示される重合体からなる材料を製造できる点である。
次に本発明に係る新規な共役高分子材料の製造方法につ
いて述べる。常法により合成されるドデカヘキサイン誘
導体分子の結晶は、まず、結晶の融点以下の温度におい
て加熱するか、または紫外線や可視光等の光線、あるい
はＸ線やγ線等の放射線の照射することにより、一般式
（３）[Chemical 9] The point is that a material consisting of the polymer shown in can be produced.
Next, a method for producing the novel conjugated polymer material according to the present invention will be described. The crystal of the dodecahexayne derivative molecule synthesized by a conventional method is first heated at a temperature below the melting point of the crystal, or irradiated with light such as ultraviolet rays or visible light, or radiation such as X-rays or γ-rays. According to the general formula (3)
【化１０】 または一般式（４）[Chemical 10] Or general formula (4)
【化１１】 （一般式（３）、（４）中Ｒ及びＲ’は[Chemical 11] (R and R ′ in the general formulas (3) and (4) are
【化１２】 または[Chemical 12] Or
【化１３】 ）で表される、一方にオクタテトライニレン基を有する
ポリジアセチレン誘導体を経由して、一般式（２）[Chemical 13] ) Represented by the general formula (2) via a polydiacetylene derivative having an octatetriylene group on one side.
【化１４】 （式中 Ｒ及びＲ’は[Chemical 14] (Wherein R and R ′ are
【化１５】 または[Chemical 15] Or
【化１６】 ）で表される共役高分子が、黒色の結晶として得られ
る。この重合体は共役高分子であるため、当然のことな
がら共鳴限界式としては一般式（２）[Chemical 16] The conjugated polymer represented by) is obtained as black crystals. Since this polymer is a conjugated polymer, as a matter of course, the resonance limit formula (2)
【化１７】 のほか、一般式（５）、（６）、（７）等の構造も考え
られる。[Chemical 17] Besides, structures of general formulas (5), (6), (7) and the like are also conceivable.
【化１８】 [Chemical 18]
【化１９】 [Chemical 19]
【化２０】 反応を定量的に進行させるためには、室温で１ヶ月程度
放置する、５０℃程度２日〜５日程度加熱する、あるい
は２０〜１００Ｍｒａｄ程度のγ線照射が適当である。[Chemical 20] In order to proceed the reaction quantitatively, it is suitable to leave it at room temperature for about 1 month, heat it at about 50 ° C. for about 2 to 5 days, or irradiate it with about 20 to 100 Mrad of γ-ray.
【０００６】[0006]
実施例１ １５，１７，１９，２１，２３，２５−テトラコンタヘ
キサインの結晶を減圧下ガラス管中に封管し、３０℃で
１ヶ月放置することにより、黒色の重合体が得られる。 元素分析値（Ｃ40Ｈ58として） 計算値(%) ；Ｃ 89.15，Ｈ 10.85 実測値(%) ；Ｃ 89.43，Ｈ 10.55 実施例２ １９，２１，２３，２５，２７，２９−オクタテトラコ
ンタヘキサインの結晶を減圧下ガラス管中に封管し、60
Ｃｏから発生するγ線を３０Ｍｒａｄ照射することによ
り、黒色の重合体が得られる。 元素分析値（Ｃ48Ｈ74として） 計算値(%) ；Ｃ 88.55，Ｈ 11.45 実測値(%) ；Ｃ 88.50，Ｈ 11.31 実施例３ １０，１２，１４，１６，１８，２０−トリアコンタヘ
キサイン−１，３０−ジオールの結晶を減圧下ガラス管
中に封管し、60Ｃｏから発生するγ線を５０Ｍｒａｄ照
射することにより、黒色の重合体が得られる。 元素分析値（Ｃ30Ｈ38Ｏ2として） 計算値(%) ；Ｃ 83.68，Ｈ 8.89 実測値(%) ；Ｃ 83.74，Ｈ 9.06 実施例４ １０，１２，１４，１６，１８，２０−トリアコンタヘ
キサイン二酸の結晶を減圧下ガラス管中に封管し、60Ｃ
ｏから発生するγ線を３０Ｍｒａｄ照射することによ
り、黒色の重合体が得られる。 元素分析値（Ｃ30Ｈ34Ｏ4として） 計算値(%) ；Ｃ 78.57，Ｈ 7.47 実測値(%) ；Ｃ 78.29，Ｈ 7.35 実施例５ ビス（ｐ−トルエンスルホン酸） ５，７，９，１１，
１３，１５−イコサヘキサイン−１，２０−ジイルの結
晶を減圧下ガラス管中に封管し、５０℃で５日加熱する
ことにより、黒色の重合体が得られる。 元素分析値（Ｃ34Ｈ30Ｏ6Ｓ2として） 計算値(%) ；Ｃ 68.21，Ｈ 5.05 実測値(%) ；Ｃ 68.43，Ｈ 4.97 実施例６ ビス（Ｎ−（ブトキシカルボニルメチレン）カルバミン
酸） ６，８，１０，１２，１４，１６−ドコサヘキサ
イン−１，２２−ジイルの結晶を減圧下ガラス管中に封
管し、60Ｃｏから発生するγ線を３０Ｍｒａｄ照射する
ことにより、黒色の重合体が得られる。 元素分析値（Ｃ36Ｈ44Ｎ2Ｏ8として） 計算値(%) ；Ｃ 68.34，Ｈ 7.01，Ｎ 4.43 実測値(%) ；Ｃ 68.44，Ｈ 7.22，Ｎ 4.32 実施例７ Ｎ−（ブトキシカルボニルメチレン）カルバミン酸
５，７，９，１１，１３，１５−トリアコンタヘキサイ
ニルの結晶を減圧下ガラス管中に封管し、60Ｃｏから発
生するγ線を３０Ｍｒａｄ照射することにより、黒色の
重合体が得られる。 元素分析値（Ｃ37Ｈ49ＮＯ4として） 計算値(%) ；Ｃ 77.72，Ｈ 8.64，Ｎ 2.45 実測値(%) ；Ｃ 77.83，Ｈ 8.89，Ｎ 2.65 実施例８ ｐ−トルエンスルホン酸 ２０−ヒドロキシ−５，７，
９，１１，１３，１５−イコサヘキサイニルのＮ−（ブ
トキシカルボニルメチレン）カルバミン酸エステルの結
晶を減圧下ガラス管中に封管し、５０℃で５日加熱する
ことにより、黒色の重合体が得られる。 元素分析値（Ｃ34Ｈ35ＮＯ7Ｓとして） 計算値(%) ；Ｃ 67.87，Ｈ 5.86，Ｎ 2.33 実測値(%) ；Ｃ 68.03，Ｈ 5.97，Ｎ 2.05Example 1 A black polymer is obtained by sealing a crystal of 15,17,19,21,23,25-tetracontahexaine in a glass tube under reduced pressure and allowing it to stand at 30 ° C. for 1 month. Elemental analysis value (as C 40 H 58 ) Calculated value (%); C 89.15, H 10.85 Measured value (%); C 89.43, H 10.55 Example 2 19,21,23,25,27,29-octatetraconta crystals Hekisain was sealed in vacuo glass tube, 60
A black polymer is obtained by irradiating 30 Mrad of γ rays generated from Co. Elemental analysis value (as C 48 H 74 ) Calculated value (%); C 88.55, H 11.45 Measured value (%); C 88.50, H 11.31 Example 3 10, 12, 14, 16, 18, 20-Triacontahexa A black polymer is obtained by sealing a crystal of in-1,30-diol in a glass tube under reduced pressure and irradiating 50 Mrad of γ-ray generated from 60 Co. Elemental analysis value (as C 30 H 38 O 2 ) Calculated value (%); C 83.68, H 8.89 Measured value (%); C 83.74, H 9.06 Example 4 10, 12, 14, 16, 18, 20-Thria The crystal of contahexaynedioic acid was sealed in a glass tube under reduced pressure, and 60 C
A black polymer is obtained by irradiating 30 Mrad of γ-ray generated from o. Elemental analysis value (as C 30 H 34 O 4 ) Calculated value (%); C 78.57, H 7.47 Measured value (%); C 78.29, H 7.35 Example 5 Bis (p-toluenesulfonic acid) 5,7,9 , 11,
A black polymer is obtained by sealing a crystal of 13,15-icosahexain-1,20-diyl in a glass tube under reduced pressure and heating at 50 ° C. for 5 days. Elemental analysis (C 34 H 30 O 6 as S 2) Calculated (%); C 68.21, H 5.05 Found (%); C 68.43, H 4.97 Example 6 Bis (N- (butoxycarbonyl methylene) carbamate ) A crystal of 6,8,10,12,14,16-docosahexain-1,22-diyl was sealed in a glass tube under reduced pressure, and γ-rays generated from 60 Co were irradiated at 30 Mrad to give a black color. A polymer of Elemental analysis value (as C 36 H 44 N 2 O 8 ) calculated value (%); C 68.34, H 7.01, N 4.43 measured value (%); C 68.44, H 7.22, N 4.32 Example 7 N- (butoxycarbonyl Methylene) carbamic acid
A black polymer was obtained by sealing 5,7,9,11,13,15-triacontahexainyl crystals in a glass tube under reduced pressure and irradiating 30 Mrad of γ-ray generated from 60 Co. To be Elemental analysis value (as C 37 H 49 NO 4 ) calculated value (%); C 77.72, H 8.64, N 2.45 measured value (%); C 77.83, H 8.89, N 2.65 Example 8 p-toluenesulfonic acid 20- Hydroxy-5,7,
Crystals of N- (butoxycarbonylmethylene) carbamic acid ester of 9,11,13,15-icosahexainyl were sealed in a glass tube under reduced pressure and heated at 50 ° C. for 5 days to give a black solid. A coalescence is obtained. Elemental analysis value (as C 34 H 35 NO 7 S) Calculated value (%); C 67.87, H 5.86, N 2.33 Measured value (%); C 68.03, H 5.97, N 2.05
【０００７】[0007]
【発明の効果】本発明に係る新規な共役高分子材料の製
造方法は、前出実施例に示した通り、新規な共役高分子
である一般式（２）The method for producing a novel conjugated polymer material according to the present invention is, as shown in the above-mentioned examples, a general formula (2) which is a novel conjugated polymer.
【化２１】 で表される重合体を、固相重合により簡便に製造する方
法として好適である。[Chemical 21] It is suitable as a method for easily producing a polymer represented by
───────────────────────────────────────────────────── フロントページの続き (72)発明者 平泉 紀久子 茨城県つくば市東１丁目１番化学技術研究 所内 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Kikuko Hiraizumi 1-1-1 Higashi, Tsukuba-shi, Ibaraki Chemical Technology Research Center
Claims (1)
晶の融点以下の温度において加熱するか、紫外線や可視
光等の光線、あるいはＸ線やγ線等の放射線を照射する
ことにより得られる、一般式（２） 【化４】 （式中 Ｒ及びＲ’は 【化５】 または 【化６】 ）で表される重合体からなることを特徴とする共役高分
子材料の製造方法。1. A general formula (1): (Wherein R and R ′ are as follows: Or [Chemical 3] ) Is obtained by heating a crystal of the dodecahexayne derivative molecule represented by) at a temperature equal to or lower than the melting point of the crystal, or by irradiating light rays such as ultraviolet rays and visible light, or radiation rays such as X-rays and γ-rays General formula (2) (In the formula, R and R ′ are as follows. Or The manufacturing method of the conjugated polymer material characterized by comprising the polymer represented by these.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3313643A JPH0686496B2 (en) | 1991-10-31 | 1991-10-31 | Method for producing novel conjugated polymer material by solid-state polymerization |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3313643A JPH0686496B2 (en) | 1991-10-31 | 1991-10-31 | Method for producing novel conjugated polymer material by solid-state polymerization |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05117328A JPH05117328A (en) | 1993-05-14 |
| JPH0686496B2 true JPH0686496B2 (en) | 1994-11-02 |
Family
ID=18043785
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3313643A Expired - Lifetime JPH0686496B2 (en) | 1991-10-31 | 1991-10-31 | Method for producing novel conjugated polymer material by solid-state polymerization |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0686496B2 (en) |
-
1991
- 1991-10-31 JP JP3313643A patent/JPH0686496B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05117328A (en) | 1993-05-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |