JPS6366227A - Polyimide obtained by reacting diacetylene bond part - Google Patents
Polyimide obtained by reacting diacetylene bond partInfo
- Publication number
- JPS6366227A JPS6366227A JP20955886A JP20955886A JPS6366227A JP S6366227 A JPS6366227 A JP S6366227A JP 20955886 A JP20955886 A JP 20955886A JP 20955886 A JP20955886 A JP 20955886A JP S6366227 A JPS6366227 A JP S6366227A
- Authority
- JP
- Japan
- Prior art keywords
- polyimide
- reacting
- formula
- diacetylene
- reaction
- 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
- 239000004642 Polyimide Substances 0.000 title claims abstract description 18
- 229920001721 polyimide Polymers 0.000 title claims abstract description 18
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 18
- 238000000034 method Methods 0.000 abstract description 18
- 239000002994 raw material Substances 0.000 abstract description 4
- 230000001747 exhibiting effect Effects 0.000 abstract description 2
- 230000009257 reactivity Effects 0.000 abstract description 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 238000006552 photochemical reaction Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 description 15
- 238000010521 absorption reaction Methods 0.000 description 8
- 150000003949 imides Chemical group 0.000 description 7
- 238000002411 thermogravimetry Methods 0.000 description 6
- 230000004580 weight loss Effects 0.000 description 6
- 238000003746 solid phase reaction Methods 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical group C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 230000020169 heat generation Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 101150030723 RIR2 gene Proteins 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000005251 gamma ray Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- 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】 するものである。[Detailed description of the invention] It is something to do.
近年、固相重合によるトポケミカル反応を用いた単結晶
ポリマーの合成は、注目されており、この手法を用いて
、種々の高弾性率を有する高結晶性高分子の開発が試み
られている。In recent years, the synthesis of single-crystalline polymers using topochemical reactions through solid-state polymerization has attracted attention, and attempts have been made to use this technique to develop various highly crystalline polymers having high elastic moduli.
（例えば、「有機非線形光学材料」、シーエムシー（１
９８５）、マクロモレキニル ケミストリー第１３４巻
、第２１９頁（１９７０）、ジャーナルオブポリマー
サイエンス 第８９巻、第１３３得ていたので、大きな
成形体として得ることができず、またポリマー自体、水
および有機溶媒に不溶なものが多いので、重合後の加工
性がきわめて悪い。(For example, "Organic nonlinear optical materials", CMC (1
985), Macromolecule Chemistry Vol. 134, p. 219 (1970), Journal of Polymers
Science Vol. 89, No. 133. Therefore, it cannot be obtained as a large molded product, and since the polymer itself is often insoluble in water and organic solvents, the processability after polymerization is extremely poor.
また、これまで合成研究されてきたトポケミカル重合性
を有するジアセチレン化合物は、ＨＯＣＨ鵞Ｃ＝ＥＣ−
Ｃ，ＥＣＣＨ２０Ｈのような水酸基を有する化合物及び
その誘導体に限られており、研究の進展が妨げられてい
た。これに対し窒素原子が導入された素材では窒素原子
の電気陰性度や凝集力が活用可能な上に、イミド環を持
たせる事による高耐熱性なども考えられ、トポケミカル
反応の可能性とその実用化へ大きな期待が持たれる。In addition, diacetylene compounds with topochemical polymerizability that have been synthesized and researched so far are HOCH 鵞C=EC-
The research has been limited to compounds with hydroxyl groups such as C, ECCH20H, and their derivatives, which has hindered the progress of research. On the other hand, materials into which nitrogen atoms are introduced can utilize the electronegativity and cohesive force of nitrogen atoms, and also have high heat resistance due to the imide ring, which increases the possibility of topochemical reactions and their practical use. There are great expectations for the future.
このような観点から、ジアセチレン基を持つポリイミド
は、非常に興味が持たれるが、従来このようなトポケミ
カル反応性を示すジアセチレン基すなわち本発明は下記
一般式で示されるくり返し単位を有し、且つジアセチレ
ン結合部を反応せしめてなるポリイミドを提供するもの
である。From this point of view, polyimides having diacetylene groups are of great interest, but conventional diacetylene groups exhibiting such topochemical reactivity, that is, polyimides of the present invention, have repeating units represented by the following general formula, Further, the present invention provides a polyimide obtained by reacting diacetylene bonding portions.
（式中Ｒ，，Ｒ２は２価の炭化水素基、２は４価の炭化
水素基である。）
本発明において、ＲＩＲ２は炭素数１〜３０の２価又、
これら炭化水素基が他の結合基で連結されていても良い
。この様な炭化水素基以外の他の結合基としては、例え
ば−ｏ−、−ｓ −、−ｓｏ、−、−、ｃｏ −。(In the formula, R,, R2 is a divalent hydrocarbon group, and 2 is a tetravalent hydrocarbon group.) In the present invention, RIR2 is a divalent hydrocarbon group having 1 to 30 carbon atoms, or
These hydrocarbon groups may be connected by other bonding groups. Examples of bonding groups other than such hydrocarbon groups include -o-, -s-, -so, -, -, and co-.
−ＮＨＣＯ−ＮＨ−、−Ｎ−Ｎ−、−ＨＣ＝Ｎ−等であ
りこれらが組み合さっていても又繰り返されていても良
い。-NHCO-NH-, -N-N-, -HC=N-, etc., and these may be combined or repeated.
ＲＩ ＋ Ｒ２として好ましいのは、合成のしやすさと
本発明において、Ｚは炭素数１〜４ｏの４価の等のよう
にヘテロ原子を有する官能基によって当該炭化水素基が
結ばれていてもよい。また、上記これらのＺのうち好捷
しいのは合成の答易さと返し単位としては、特に制限は
ないが、好ましくは、アミド、イミド、アミドイミド、
エステル、エーテル等のくり返し単位が好ましく用いら
れる。Preferred as RI + R2 is ease of synthesis and in the present invention, Z may be a functional group having a heteroatom such as a tetravalent one having 1 to 4 carbon atoms, to which the hydrocarbon group may be bonded. . Further, among these Z, preferable ones are amide, imide, amidimide, although there is no particular restriction in terms of ease of synthesis and return unit.
Repeating units such as esters and ethers are preferably used.
このような共重合物において、本発明の一般式で示され
るくり返し単位の量は特に制限はないが好ましくけ１モ
ルチ以上、特には５モルチ以上である。In such a copolymer, the amount of repeating units represented by the general formula of the present invention is not particularly limited, but is preferably 1 molti or more, particularly 5 molti or more.
本発明のジアセチレン結合部を反応せしめてなるポリイ
ミドの化学構造としては赤外分光法（以下ＩＲと略す）
、レーザーラマン、Ｘ線回折法、ＩＩ ＩＩ
レン基がトランス−１，４−付加した式０２式■または
、式■と式■の平衡混合物であることが示唆される。The chemical structure of the polyimide obtained by reacting the diacetylene bond of the present invention is determined by infrared spectroscopy (hereinafter abbreviated as IR).
, Laser Raman, X-ray diffraction method, III It is suggested that the formula 02 is the formula (2) in which the ren group is trans-1,4-added, or an equilibrium mixture of the formula (2) and the formula (2).
Ｏ
しかし本発明のジアセチレン結合で反応せしめてなるポ
リイミドの繰り返し単位の中には式■。O However, some of the repeating units of the polyimide reacted with diacetylene bonds of the present invention have the formula (■).
式■または式■と式■の平衡混合物以外の繰り返し単位
を部分的に含む可能性もあり、例えば原料ヤあるジアセ
チレン基含有ポリイミド
し単位として有するポリイミドが、１．２付加した９一
式■、■などが含まれていてもよい。また原料で返し単
位として有するポリイミドが含まれていてもよい。There is a possibility that repeating units other than the formula (■) or an equilibrium mixture of the formula (2) and the formula (2) may be partially included. ■ etc. may be included. The raw material may also contain polyimide as a return unit.
また、本発明のジアセチレン結合部を反応せしめてなる
ポリイミドに、例えば他のジアセチレン化合物や一般的
な不飽和結合を持つ化合物が反応定量する事により推定
可能である。Furthermore, it can be estimated by quantifying the reaction of, for example, other diacetylene compounds or general compounds having unsaturated bonds with the polyimide obtained by reacting the diacetylene bond of the present invention.
本発明のジアセチレン結合部を反応せしめてなるポリイ
ミドの製造法としては例えば、原料のし単位として有す
るポリイミドを、光反応法では低圧、中圧またけ博ｊ圧
水銀ランプを用いてのＵＶ照射法％ Ｍｉ子線照射法、
γ線照射法、プラズマ反応法にて反応させることにより
合成できる。As a method for producing polyimide made by reacting the diacetylene bond of the present invention, for example, a photoreaction method involves UV irradiation using a high-pressure mercury lamp that spans between low and medium pressures. method% Mi coron beam irradiation method,
It can be synthesized by reaction using γ-ray irradiation method or plasma reaction method.
一方熱反応法としては、例えば原料である単位としで有
するポリイミドを用い、基本的に分単位として有するポ
リイミドを用い一定時間の加圧処理することにより合成
できる。On the other hand, as a thermal reaction method, for example, synthesis can be performed by using a polyimide having units as a raw material and subjecting the polyimide having units of minutes to pressure treatment for a certain period of time.
本発明のジアセチレン結合部を反応せしめてなるポリイ
ミドを製造する場合、」１記の光反応法、熱反応法、加
圧法を単独で用いてもよいが、２つ以上の方法を組み合
せてもよい。例えば、加熱（。When producing a polyimide obtained by reacting the diacetylene bond of the present invention, the photoreaction method, thermal reaction method, and pressurization method described in 1. may be used alone, but two or more methods may be used in combination. good. For example, heating (.
なから加圧法で製造するといった方法も適用でき、むし
ろその方が好ましい。前記の光反応法、熱反応法、加圧
法において、過酸化物、アゾ化合物、粉体でもよいが単
結晶であることが特に好ましい。Therefore, a method of manufacturing by pressurization can also be applied, and this is rather preferable. In the photoreaction method, thermal reaction method, and pressurization method, peroxides, azo compounds, and powders may be used, but single crystals are particularly preferred.
上記のジアセチレン結合部を反応せしめてなるポリイミ
ドの製造法において、光反応法の場合用ないが、好まし
くは基本的に原料分解点より低い温度である。また、反
応時間についても制限はないが、好ましくＦｉ１分から
１０時間である。In the method for producing polyimide by reacting the diacetylene bond described above, the temperature is preferably lower than the decomposition point of the raw material, although it is not used in the case of a photoreaction method. There is also no restriction on the reaction time, but it is preferably Fi 1 minute to 10 hours.
一方加圧法において、圧力は特に制限はないが、好まし
くは２０ａｔｍから１１００００ａｔである。また、反
応時間についても制限はなく、好捷しくけ工秒間から２
０時間である。On the other hand, in the pressurization method, the pressure is not particularly limited, but is preferably from 20 atm to 110,000 atm. There is also no limit to the reaction time, from 2 seconds to 2 seconds.
It is 0 hours.
〔発明の効果〕 本発明のジアセチレン結合部を反応せしめてなる。〔Effect of the invention〕 The diacetylene bond of the present invention is reacted.
父、その用途に応じては、例えば粉体状、塊状、薄片状
、繊維状、織物状、フィルム状、シート状、綿状、棒状
、板状、管状、懸濁状など種々の形状で使用可能であり
、又無機や有機の線維状物、フィルム状物、塊状物、織
物状物、綿状物、管状物、シ〜１４−
−ト秋物、板状物、粉状物、薄片状物と混合して用いた
り、他の硬化性樹脂や高分子材料あるいは着色材や安定
化材料などと混合して用いる事も可能である。Depending on the purpose, it is used in various shapes such as powder, lump, flake, fiber, fabric, film, sheet, cotton, rod, plate, tube, suspension, etc. Possible, and inorganic or organic fibrous materials, film-like materials, lump-like materials, textile-like materials, cotton-like materials, tubular materials, sheet-like materials, plate-like materials, powder-like materials, flaky materials. It can also be used in combination with other curable resins, polymeric materials, colorants, stabilizing materials, etc.
以上の様に、良好な耐熱性、弾性率を示す事例より、特
に′耐熱性の要求される分野に極めて有用である。As mentioned above, since the examples show good heat resistance and elastic modulus, they are extremely useful particularly in fields where heat resistance is required.
実施例−１
又示差熱熱量計にて反応熱を測定したところ、発熱がほ
とんど無く熱固相反応した。この処理物の熱重量分析を
空気中で測定したところ、３２０℃まで減量は全く見ら
れず耐熱性が良好であった。Example 1 When the reaction heat was measured using a differential calorimeter, there was almost no heat generation, and a thermal solid phase reaction occurred. When this treated product was subjected to thermogravimetric analysis in air, no weight loss was observed up to 320° C., and the heat resistance was good.
実施例−２
実施例−１の化合物を中圧水銀ランプを用いて１時間の
紫外線照射を行なった。処理物は赤色となり赤外吸収ス
ペクトルより、１７８０ｃ１ｎ−’のイミドに係る吸収
に対１．て２１９５ｃｒｎ−’の三重結合の吸気中で測
定したところ、３２０℃まで減量は全く見られず耐熱性
が良好であった。Example 2 The compound of Example 1 was irradiated with ultraviolet rays for 1 hour using a medium pressure mercury lamp. The treated product turned red, and the infrared absorption spectrum showed that the absorption related to the imide of 1780c1n-' was 1. When the triple bond of 2195 crn-' was measured in the intake air, no weight loss was observed up to 320° C., and the heat resistance was good.
実施例−３
対して２１９５ｃｒｎ＠ の三重結合の吸収がはとんと
無くなった。父、実施例−１と同様に反応熱を定量した
ところ、反応熱が無くなり、熱・圧による固相反応をし
た。この処理物の熱重量分析を空気中で測定したところ
、３２０℃まで減量は全く見られず耐熱性が良好であっ
た。In contrast to Example 3, the triple bond absorption of 2195crn@ was completely eliminated. When the reaction heat was quantified in the same manner as in Example 1, there was no reaction heat, indicating a solid phase reaction due to heat and pressure. When this treated product was subjected to thermogravimetric analysis in air, no weight loss was observed up to 320° C., and the heat resistance was good.
実施例−４
処理物の熱重量分析を空気中で測定したところ、３４０
℃まで減量は全く見られず耐熱性が良好であった。Example-4 Thermogravimetric analysis of the treated material was performed in air, and the result was 340
No weight loss was observed up to ℃, and the heat resistance was good.
実施例−５
を実施例−１と同様の方法で処理した。処理物は赤色と
なり、赤外吸収スペクトルより１７８０ｃＩｎ−”のイ
ミドに係る吸収に対して２１９５６ｎ−’の三重結合が
減少した（ピーク高さの比）。又、実施例−１と同様に
反応熱を測定したところ、未処理物に比べ約２０チ減少
し熱固相反応した。この処理物のを実施例−３と同様の
方法で処理した。処理物は赤色となり、赤外吸収スペク
トルより１７８０ｃｍ−’のイミドに係る吸収に対して
２１９５ｃＩｎ−’の三重結合がほとんど見られなかっ
た。又、実施例−１と同様に反応熱を測定したところ、
反応熱ｉｉ姑られず熱圧による固相反応をした。Example-5 was treated in the same manner as Example-1. The treated product turned red, and the infrared absorption spectrum showed that the triple bond of 21956n-' decreased compared to the imide-related absorption of 1780cIn-' (peak height ratio). Also, as in Example-1, the reaction heat When measured, it decreased by about 20 cm compared to the untreated product, indicating a thermal solid phase reaction.This treated product was treated in the same manner as in Example 3.The treated product turned red, and the infrared absorption spectrum showed a temperature of 1780 cm. -' The triple bond of 2195cIn-' was hardly observed in the absorption related to the imide.Also, when the reaction heat was measured in the same manner as in Example-1,
A solid phase reaction was carried out under heat and pressure without reducing the heat of reaction.
この処理物の熱重量分析を空気中で測定したところ、３
５０℃まで全く減量は見られず鉗子熱性が良好であった
。When thermogravimetric analysis of this treated material was performed in air, 3
No weight loss was observed up to 50°C, and forceps heat resistance was good.
実施例−フ
イミドに係る吸収に対して、２１９５ｃｒｎ−’の三重
結合の吸収が大巾に減少した（ピーク高さの比）。Example - The absorption of the triple bond of 2195crn-' was significantly reduced (ratio of peak heights) with respect to the absorption related to the imide.
又、示差熱量計にて反応熱を測定したところ、発熱がほ
とんど無くなり熱固相反応した。この処理物の熱重量分
析を空気中で測定したところ、３４０℃まで減Ｉは無く
１耐熱性が良好であった。In addition, when the reaction heat was measured using a differential calorimeter, there was almost no heat generation, indicating a thermal solid phase reaction. When thermogravimetric analysis of this treated product was performed in air, there was no decrease in I up to 340° C. and the heat resistance was good.
実施例−８
なり、赤外吸収スペクトルより１７７８ｍ−１のイミド
に係る吸収に対して２１９３ｍ−’の三重結合の吸収が
大巾に減少した（ピーク高さの比）。Example 8 According to the infrared absorption spectrum, the absorption of the triple bond at 2193 m-' was significantly reduced compared to the imide-related absorption at 1778 m-1 (peak height ratio).
父、示差熱量計にて反応熱を測定したところ、発熱がほ
とんど無くなり熱同相反応した。この処理物の熱重量分
析を空気中で測定したところ、３３０℃まで減量は無く
耐熱性が良好であった。When my father measured the heat of reaction with a differential calorimeter, there was almost no heat generation, indicating a thermal in-phase reaction. Thermogravimetric analysis of this treated product in air showed that there was no weight loss up to 330° C. and the heat resistance was good.
％許出願人 工業技術院長Percentage applicant: Director of the Agency of Industrial Science and Technology
Claims (1)
チレン結合部を反応せしめてなるポリイミド ▲数式、化学式、表等があります▼ （式中Ｒ＿１、Ｒ＿２は２価の炭化水素基、Ｚは４価の
炭化水素基である。）[Claims] Polyimide having repeating units represented by the following general formula and reacted with diacetylene bonding parts ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_1 and R_2 are divalent carbonized Hydrogen group, Z is a tetravalent hydrocarbon group.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20955886A JPS6366227A (en) | 1986-09-08 | 1986-09-08 | Polyimide obtained by reacting diacetylene bond part |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20955886A JPS6366227A (en) | 1986-09-08 | 1986-09-08 | Polyimide obtained by reacting diacetylene bond part |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6366227A true JPS6366227A (en) | 1988-03-24 |
| JPH0439485B2 JPH0439485B2 (en) | 1992-06-29 |
Family
ID=16574811
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20955886A Granted JPS6366227A (en) | 1986-09-08 | 1986-09-08 | Polyimide obtained by reacting diacetylene bond part |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6366227A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6315828A (en) * | 1986-07-08 | 1988-01-22 | Agency Of Ind Science & Technol | Diacetylene group-containing amic acid derivative copolymer and imide copolymer |
| JPS6315827A (en) * | 1986-07-08 | 1988-01-22 | Agency Of Ind Science & Technol | Diacetylene group-containing polyamic acid and polyimide |
-
1986
- 1986-09-08 JP JP20955886A patent/JPS6366227A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6315828A (en) * | 1986-07-08 | 1988-01-22 | Agency Of Ind Science & Technol | Diacetylene group-containing amic acid derivative copolymer and imide copolymer |
| JPS6315827A (en) * | 1986-07-08 | 1988-01-22 | Agency Of Ind Science & Technol | Diacetylene group-containing polyamic acid and polyimide |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0439485B2 (en) | 1992-06-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |