JPH0755984B2 - Method for producing aromatic polyamide - Google Patents
Method for producing aromatic polyamideInfo
- Publication number
- JPH0755984B2 JPH0755984B2 JP61142871A JP14287186A JPH0755984B2 JP H0755984 B2 JPH0755984 B2 JP H0755984B2 JP 61142871 A JP61142871 A JP 61142871A JP 14287186 A JP14287186 A JP 14287186A JP H0755984 B2 JPH0755984 B2 JP H0755984B2
- Authority
- JP
- Japan
- Prior art keywords
- dicarboxylic acid
- represented
- formula
- general formula
- polyamide
- 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 - Fee Related
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- Polyamides (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、新規な芳香族ポリアミドおよびその製造方法
に関する。TECHNICAL FIELD The present invention relates to a novel aromatic polyamide and a method for producing the same.
本発明のポリアミドは耐熱性に優れた樹脂であり、また
ポリベンズオキサゾール樹脂の原料として有用なもので
ある。The polyamide of the present invention is a resin having excellent heat resistance and is also useful as a raw material for a polybenzoxazole resin.
従来より芳香族ポリベンズオキサゾールが、引張り強
度、曲げ強度、衝撃強さなどの機械的性質、熱変形温度
や熱分解などの熱的性質、耐マーク、誘電損失などの電
気的性質、耐炎性、寸法安定性などにおいて、優れた性
質を有することが知られている。Traditionally, aromatic polybenzoxazole has been used for mechanical properties such as tensile strength, bending strength, impact strength, thermal properties such as thermal deformation temperature and thermal decomposition, electrical resistance such as marks, dielectric loss, flame resistance, It is known to have excellent properties such as dimensional stability.
しかしながら、これらのポリベンズオキサゾールは、成
形性が悪いという欠点を持つており、そのため、予め可
溶性のポリアミドにて成形し、しかるのちにポリベンズ
オキサゾールとする方法が提案されている(特公昭42−
19272号)。However, these polybenzoxazoles have the drawback of poor moldability, and therefore, a method has been proposed in which the polybenzoxazole is molded in advance with a soluble polyamide and then the polybenzoxazole is used (Japanese Patent Publication No.
No. 19272).
しかし、この種のポリアミドにおいては、可溶溶媒の種
類が限定され、工業的なものではない。However, in this type of polyamide, the type of soluble solvent is limited, and it is not industrial.
一般にプラスチツクにおいては、成型性に関する評価が
極めて重要な位置を占めており、たとえそのものが本質
的に優れた性質を持つていても、成型性が悪いと、製品
を経済的に製造することができないばかりでなく、その
特性を充分に発揮することができない。Generally, in plastics, the evaluation of moldability occupies an extremely important position, and even if the mold itself has excellent properties, if the moldability is poor, the product cannot be economically manufactured. Not only that, but its characteristics cannot be fully exhibited.
成型性は軟化温度(又は溶融温度)と、溶解性の二つの
性質に係る問題である。すなわち、軟化温度や溶融温度
が高いと、射出成型法によつて製品を作る際に高い金型
温度が必要となり、コストが高くなる。又、高温での射
出成型はポリマーの熱分解を促し、製品の品質を悪くす
る。溶液から紡糸やフイルム成型を行なう際には、取扱
いが容易で安価な溶媒にポリマーが易溶でなければなら
ない。一部の公知の芳香族ポリアミドのように、強い鉱
酸にしか溶解しない場合は、溶媒の腐食性が強いため装
置が極めて高価となり、又、技術的にも難しいことが知
られている。Formability is a problem related to two properties: softening temperature (or melting temperature) and solubility. That is, when the softening temperature and the melting temperature are high, a high mold temperature is required when manufacturing a product by the injection molding method, and the cost becomes high. Also, injection molding at high temperature promotes thermal decomposition of the polymer and deteriorates product quality. When spinning or film-forming from a solution, the polymer must be easily soluble in an inexpensive solvent that is easy to handle. It is known that, when it is soluble only in a strong mineral acid like some known aromatic polyamides, the apparatus is extremely expensive due to the strong corrosiveness of the solvent and is technically difficult.
本発明者らは、上記、公知の芳香族ポリアミドの欠点を
克服し、しかもその優れた性質を繊維するような新しい
ポリマーの開発に努力した結果、2.2−ビス(3−アミ
ノ−4−ヒドロキシフエニル)ヘキサフルオロプロパン
を成分に持つ芳香族ポリアミドが、各種の有機溶媒に可
溶であることを見出し、本発明を完成した。As a result of efforts by the present inventors to develop a new polymer which overcomes the above-mentioned drawbacks of known aromatic polyamides and has excellent fiber properties, 2.2-bis (3-amino-4-hydroxyphenol) was obtained. We have found that an aromatic polyamide containing (enyl) hexafluoropropane as a component is soluble in various organic solvents, and completed the present invention.
すなわち、本発明は、 一般式(I) (式中、Rは、 (Yは、単結合、 を示す。)で表される2価の芳香族基を示す。)で表さ
れる繰り返し単位からなる芳香族ポリアミドの製造方法
であって、2.2−ビス(3−アミノ−4−ヒドロキシフ
エニル)ヘキサフルオロプロパンと、 一般式(II) (式中、Rは前記と同じ。)で表わされるジカルボン酸
または一般式(III)で表わされるジカルボン酸ジハラ
イド、 (式中、Rは前記と同じ。Xはハロゲンを示す。)もし
くは、一般式(IV)で表わされるジカルボン酸ジエステ
ル (式中、Rは前記と同じ。R′はアルキル基又はフエニ
ル基を示す。)のいずれかとを反応させることを特徴と
する製造法である。That is, the present invention provides the compound represented by the general formula (I) (In the formula, R is (Y is a single bond, Indicates. ) Is a divalent aromatic group. ) A method for producing an aromatic polyamide comprising a repeating unit represented by the formula: 2.2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane; (Wherein R is the same as above) or a dicarboxylic acid dihalide represented by the general formula (III), (In the formula, R is the same as above. X represents halogen.) Or a dicarboxylic acid diester represented by the general formula (IV) (In the formula, R is the same as the above. R'represents an alkyl group or a phenyl group.).
本発明において、一般式(II)で表わされるジカルボン
酸、一般式(III)で表わされるジカルボン酸ジハライ
ド、一般式(IV)で表わされるジカルボン酸ジエステル
としては、相当する公知の化合物総てが使用一般式(I
I)〜(IV)において、Rが (Yは、単結合、 を示す。)で表される2価の芳香族基であるものが好ま
しい。具体的には、例えば、イソフタル酸、テレフタル
酸、4.4′−ビフエニルジカルボン酸、ビフエニルエー
テル−4.4′−ジカルボン酸、ベンゾフエノン−4.4′−
ジカルボン酸、ベンゾスルホン−4.4′−ジカルボン
酸、2.6−ナフタレンジカルボン酸、ジフエニルメタン
−4.4′−ジカルボン酸、4.4′−イソプロピリデンジフ
エニル−1.1′−ジカルボン酸、4.4′−ヘキサフルオロ
イソプロピリデンジフエニル−1.1′−ジカルボン酸、
イソフタル酸ジクロリド、テレフタル酸ジクロリド、4.
4′−ビフエニルジカルボン酸ジクロリド、ビフエニル
エーテル−4.4′−ジカルボン酸ジクロリド、ベンゾフ
エノン−4.4′−ジカルボン酸ジクロリド、ベンゾスル
ホン−4.4′−ジカルボン酸ジクロリド、2.6−ナフタレ
ンジカルボン酸ジクロリド、ジフエニルメタン−4.4′
−ジカルボン酸ジクロリド、4.4′−イソプロピリデン
ジフエニル−1.1′−ジカルボン酸ジクロリド、4.4′−
ヘキサフルオロイソプロピリデンジフエニル−1.1′−
ジカルボル酸ジクロリド、イソフタル酸ジフエニル、テ
レフタル酸ジフエニル、4.4′−ビフエニルジカルボン
酸ジフエニル、ビフエニルエーテル4.4′−ジカルボン
酸ジフエニル、ベンゾフエノン−4.4′−ジカルボン酸
ジフエニル、ベンゾスルホン−4.4′−ジカルボン酸ジ
フエニル、2.6−ナフタレンジカルボン酸ジフエニル、
ジフエニルメタン−4.4′−ジカルボン酸ジフエニル、
4.4′−イソプロピリデンジフエニル−1.1′−ジカルボ
ン酸ジフエニル、4.4′−ヘキサフルオロイソプロピリ
デンジフエニール−1.1′−ジカルボン酸ジフエニルな
どが有効である。なお、これらの芳香族ジカルボン酸、
芳香族ジカルボン酸ジハライド、芳香族ジカルボン酸ジ
エステルは、単独で用いることも、また二種類以上を混
合して用いることも可能である。この場合には対応する
共重合体が得られるものである。In the present invention, as the dicarboxylic acid represented by the general formula (II), the dicarboxylic acid dihalide represented by the general formula (III), and the dicarboxylic acid diester represented by the general formula (IV), all corresponding known compounds are used. General formula (I
In I) to (IV), R is (Y is a single bond, Indicates. And a divalent aromatic group represented by Specifically, for example, isophthalic acid, terephthalic acid, 4.4'-biphenyldicarboxylic acid, biphenyl ether-4.4'-dicarboxylic acid, benzophenone-4.4'-
Dicarboxylic acid, benzosulfone-4.4'-dicarboxylic acid, 2.6-naphthalenedicarboxylic acid, diphenylmethane-4.4'-dicarboxylic acid, 4.4'-isopropylidene diphenyl-1.1'-dicarboxylic acid, 4.4'-hexafluoroisopropylidene diphenyl- 1.1'-dicarboxylic acid,
Isophthalic acid dichloride, terephthalic acid dichloride, 4.
4'-biphenyldicarboxylic acid dichloride, biphenyl ether-4.4'-dicarboxylic acid dichloride, benzophenone-4.4'-dicarboxylic acid dichloride, benzosulfone-4.4'-dicarboxylic acid dichloride, 2.6-naphthalenedicarboxylic acid dichloride, diphenylmethane-4.4 '
-Dicarboxylic acid dichloride, 4.4'-isopropylidene diphenyl-1.1'-dicarboxylic acid dichloride, 4.4'-
Hexafluoroisopropylidene diphenyl-1.1'-
Dicarboyl dichloride, diphenyl isophthalate, diphenyl terephthalate, 4.4'-biphenyl dicarboxylic acid diphenyl, biphenyl ether 4.4'-dicarboxylic acid diphenyl, benzophenone-4.4'-dicarboxylic acid diphenyl, benzosulfone-4.4'-dicarboxylic acid diphenyl, 2.6-diphenylnaphthalenedicarboxylate,
Diphenylmethane-4.4'-dicarboxylic acid diphenyl,
4.4'-isopropylidene diphenyl-1.1'-dicarboxylic acid diphenyl, 4.4'-hexafluoroisopropylidene diphenyl-1.1'-dicarboxylic acid diphenyl, etc. are effective. Incidentally, these aromatic dicarboxylic acids,
The aromatic dicarboxylic acid dihalide and aromatic dicarboxylic acid diester can be used alone or in combination of two or more kinds. In this case, the corresponding copolymer is obtained.
本発明の製造法において2.2′−ビス(3−アミノ−4
−ヒドロキシフエニル)ヘキサフルオロプロパンと、一
般式(II)で表わされる芳香族ジカルボン酸との反応で
は、N.N−ジメチルホルムアミド、N.N−ジメチルアセト
アミド、N−メチル−2−ピロリドンなどの有機溶媒中
で室温ないし溶媒の沸点の範囲で、また一般式(III)
で表わされる芳香族ジカルボン酸ジハライドとの反応
は、同様の溶媒中で−10〜50℃の範囲で反応させる。ま
た、2.2′−ビス(3−アミノ−4−ヒドロキシフエニ
ル)ヘキサフルオロプロパンと一般式(IV)で表わされ
る芳香族ジカルボン酸ジエステルとの反応は50〜300℃
の範囲が好ましい。In the production method of the present invention, 2.2'-bis (3-amino-4
-Hydroxyphenyl) hexafluoropropane and an aromatic dicarboxylic acid represented by the general formula (II) are reacted in an organic solvent such as NN-dimethylformamide, NN-dimethylacetamide, N-methyl-2-pyrrolidone. In the range of room temperature to the boiling point of the solvent, and the general formula (III)
The reaction with the aromatic dicarboxylic acid dihalide represented by is carried out in the same solvent in the range of -10 to 50 ° C. Further, the reaction between 2.2'-bis (3-amino-4-hydroxyphenyl) hexafluoropropane and the aromatic dicarboxylic acid diester represented by the general formula (IV) is 50 to 300 ° C.
Is preferred.
以下、実施例によつて本発明をより詳しく説明するが、
これに限定されるものではない。Hereinafter, the present invention will be described in more detail with reference to Examples.
It is not limited to this.
(実施例−1) 窒素ガス導入口を備えた容量50mlの三つ口フラスコに、
2.2−ビス(3−アミノ−4−ヒドロキシフエニル)ヘ
キサフルオロプロパン0.915gを採り、ジメチルアセトア
ミド5mlに溶解する。この溶液をドライアイス−アセト
ン浴で凍結し、そこにイソフタル酸クロリド0.508gを添
加する。次に氷冷浴に切替え、ゆつくり撹拌すると、溶
液が徐々に融けてくる。そのまま窒素ガス雰囲気中で5
時間撹拌を続け、ポリアミドを得た。(Example-1) In a three-necked flask having a capacity of 50 ml equipped with a nitrogen gas inlet,
2. Take 0.915 g of 2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane and dissolve in 5 ml of dimethylacetamide. This solution is frozen in a dry ice-acetone bath, to which 0.508 g of isophthalic acid chloride is added. Next, switch to an ice-cooled bath and gently stir to slowly melt the solution. 5 as it is in a nitrogen gas atmosphere
The stirring was continued for a period of time to obtain a polyamide.
生成物の赤外線吸光分析により1650cm-1、1600cm-11の
アミドの吸収を確認した。又、元素分析の結果は次のと
おりであり、 理論値(%) 実測値(%) C H N C H N 55.66 2.84 5.64 55.46 2.61 5.78 式(1)で表わされるポリアミドであることを確認し
た。Infrared absorption analysis of the product confirmed absorption of amide at 1650 cm -1 and 1600 cm -11 . The results of elemental analysis are as follows, and it was confirmed that the polyamide was a theoretical value (%) actual measurement value (%) C H N C H N 55.66 2.84 5.64 55.46 2.61 5.78 Formula ( 1 )
生成物の固有粘度は硫酸中、30℃でηinh=0.08dL/gで
あつた。 The intrinsic viscosity of the product was ηinh = 0.08 dL / g at 30 ° C. in sulfuric acid.
このポリアミドをガラス管に入れ、1mmHg以下に減圧し
ながら250℃で20時間加熱し容易にポリベンズオキサゾ
ールを得た。This polyamide was put in a glass tube and heated at 250 ° C. for 20 hours under reduced pressure of 1 mmHg or less to easily obtain polybenzoxazole.
(実施例−2) (実施例−1)と同じ方法で、2.2−ビス(3−アミノ
−4−ヒドロキシフエニル)ヘキサフルオロプロパン0.
915g(0.25mmol)と、2.2−ビス(4−クロロカルボニ
ルフエニル)ヘキサフルオロプロパン1.07g(0.25mmo
l)を反応させポリアミドを得た。生成物の赤外線明光
分析により1650cm-1、1600cm-1のアミドの吸収を確認し
た。また、元素分析の結果は次のとおりであり、 理論値(%) 実測値(%) C H N C H N 53.20 2.51 3.88 53.17 2.34 3.91 式(2)で示されるポリアミドであることを確認した。Example-2 By the same method as in Example-1, 2.2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane.
915 g (0.25 mmol) and 2.2-bis (4-chlorocarbonylphenyl) hexafluoropropane 1.07 g (0.25 mmo
l) was reacted to obtain polyamide. 1650 cm -1 by infrared Meiko analysis of the product confirmed the absorption of amide 1600 cm -1. The results of elemental analysis are as follows, and it was confirmed that the polyamide was a theoretical value (%) actual measurement value (%) C H N C H N 53.20 2.51 3.88 53.17 2.34 3.91 Formula ( 2 ).
生成物の固有粘度は、硫酸中、30℃でηinh=0.15dL/g
であった。 The intrinsic viscosity of the product is η inh = 0.15 dL / g at 30 ℃ in sulfuric acid.
Met.
(実施例3) 還流冷却器と窒素ガス導入口を備えた容量100mlのフラ
スコに2,2−ビス(3−アミノ−4−ヒドロキシフエニ
ル)ヘキサフルオロプロパン(1,830g、5mmol)、4.4′
−オキシジ安息香酸(1,290g、5mmol)N−メチルピロ
リドン(10ml)、ピリジン(2.5ml)、亜リン酸トリフ
エニル(3.1g、10mmol)、塩化リチウム(0.5g)を採
り、窒素ガス雰囲気中、100℃に加熱し、6時間撹拌す
る。次に反応溶液を多量の水中に徐々に投入し、白色の
固体を得た。このものの赤外線吸光分析により、1,650c
m-1、1,600cm-1、のアミドの吸収を確認した。また元素
分析の結果は次のとおりであり、 理論値(%) 実測値(%) C H N C H N 59.19 3.08 4.76 59.09 3.13 4.85 式(3)で表わされるポリアミドであることを確認し
た。(Example 3) 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane (1,830 g, 5 mmol), 4.4 'was placed in a 100 ml-volume flask equipped with a reflux condenser and a nitrogen gas inlet.
-Oxydibenzoic acid (1,290 g, 5 mmol) N-methylpyrrolidone (10 ml), pyridine (2.5 ml), triphenyl phosphite (3.1 g, 10 mmol), lithium chloride (0.5 g) were taken, and 100 Heat to ° C and stir for 6 hours. Next, the reaction solution was gradually poured into a large amount of water to obtain a white solid. Infrared absorption spectrum of this product showed 1,650c
The absorption of amide at m -1 , 1,600 cm -1 was confirmed. The results of elemental analysis are as follows, and it was confirmed that the polyamide was a theoretical value (%) actual measurement value (%) C H N C H N 59.19 3.08 4.76 59.09 3.13 4.85 Formula ( 3 )
生成物の固有粘度は硫酸中、30℃で0.1dL/gであつた。 The inherent viscosity of the product was 0.1 dL / g in sulfuric acid at 30 ° C.
(実施例4) 実施例1〜3により得た化合物(1)〜(3)の有機溶
剤に対する溶解性を測定した。その結果を第1表に示
す。Example 4 Solubility of the compounds ( 1 ) to ( 3 ) obtained in Examples 1 to 3 in an organic solvent was measured. The results are shown in Table 1.
なお、比較のため従来公知のポリアミドとして化合物
(4)、化合物(5)を調製し、同様に有機溶剤に対す
る溶解性を測定した。For comparison, Compound ( 4 ) and Compound ( 5 ) were prepared as conventionally known polyamides, and the solubility in an organic solvent was similarly measured.
既知の方法により、2.2−ビス(3−アミノ−4−ヒド
ロキシフエニル)プロパンと、イソフタル酸クロリドを
ジメチルアセトアミド溶媒中で反応させた。 2.2-Bis (3-amino-4-hydroxyphenyl) propane was reacted with isophthalic acid chloride in a dimethylacetamide solvent by known methods.
既知の方法により、4.4′−ジアミノ−3.3′−ジヒドロ
キシビフエニルとイソフタル酸クロリドをジメチルアセ
トアシド溶媒中で反応させた。 4.4'-Diamino-3.3'-dihydroxybiphenyl and isophthalic acid chloride were reacted in a dimethylacetoside solvent by known methods.
〔発明の効果〕 本発明は一般式(I)で表わされる新規な芳香族ポリア
ミドおよびこの有利な製造方法を提供する。従来この種
の芳香族ポリアミドは有機溶媒に対する溶解性が必ずし
も十分でないのに対し、本発明の芳香族ポリアミドは各
種の有機溶媒に可溶であり、成形が容易で、しかも優れ
た耐熱性、機械的特性を有するので、工業材料としての
価値が大きい。また環化反応により容易に対応するポリ
ベンズオキサゾールとすることができる。 EFFECTS OF THE INVENTION The present invention provides a novel aromatic polyamide represented by the general formula (I) and an advantageous production method thereof. Conventionally, this type of aromatic polyamide is not always sufficiently soluble in organic solvents, whereas the aromatic polyamide of the present invention is soluble in various organic solvents, easy to mold, and has excellent heat resistance and mechanical properties. Since it has specific characteristics, it has great value as an industrial material. Further, the corresponding polybenzoxazole can be easily obtained by the cyclization reaction.
Claims (1)
ェニル)ヘキサフルオロプロパンと、 一般式 (式中、Rは、 (Yは、単結合、 を示す。)で表される2価の芳香族基を示す。)で表さ
れるジカルボン酸、 一般式 (式中、Rは前記と同じ。Xはハロゲンを示す。)で表
されるジカルボン酸ジハライド、または、 一般式 (式中、Rは前記と同じ。R′はアルキル基またはフェ
ニル基を示す。)で表されるジカルボン酸ジエステルの
いずれかとを反応させることを特徴とする、 一般式 (式中、Rは前記と同じ。)で表される繰り返し単位か
らなる芳香族ポリアミドの製造方法。1. 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane represented by (In the formula, R is (Y is a single bond, Indicates. ) Is a divalent aromatic group. ) A dicarboxylic acid represented by the general formula (Wherein R is the same as above, X is halogen), or a dicarboxylic acid dihalide represented by the formula: (Wherein R is the same as above, R'represents an alkyl group or a phenyl group), and is reacted with either dicarboxylic acid diester represented by the general formula (In the formula, R is the same as the above.) A method for producing an aromatic polyamide comprising a repeating unit.
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61142871A JPH0755984B2 (en) | 1986-06-20 | 1986-06-20 | Method for producing aromatic polyamide |
GB08704914A GB2188936B (en) | 1986-03-06 | 1987-03-03 | Aromatic polyamides and polybenoxazoles having diphenylhexafluoropropane units |
FR878703006A FR2595362B1 (en) | 1986-03-06 | 1987-03-05 | AROMATIC POLYAMIDES AND POLYBENZOXAZOLES HAVING DIPHENYLHEXAFLUOROPROPANE UNITS AND THEIR PREPARATION PROCESS |
DE19873707125 DE3707125A1 (en) | 1986-03-06 | 1987-03-05 | AROMATIC POLYAMIDES AND POLYBENZOXAZOLES WITH DIPHENYLHEXAFLUORPROPANE UNITS |
IT19612/87A IT1202647B (en) | 1986-03-06 | 1987-03-06 | AROMATIC POLYAMIDS AND POLYBENZOSSAZOLS WITH DIFENYLESA-FLUOROPROPANE UNIT |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61142871A JPH0755984B2 (en) | 1986-06-20 | 1986-06-20 | Method for producing aromatic polyamide |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS63318A JPS63318A (en) | 1988-01-05 |
JPH0755984B2 true JPH0755984B2 (en) | 1995-06-14 |
Family
ID=15325537
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP61142871A Expired - Fee Related JPH0755984B2 (en) | 1986-03-06 | 1986-06-20 | Method for producing aromatic polyamide |
Country Status (1)
Country | Link |
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JP (1) | JPH0755984B2 (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SG104255A1 (en) | 1998-09-29 | 2004-06-21 | Sumitomo Bakelite Co | Polybenzoxazole resin and precursor thereof |
JP2000128984A (en) * | 1998-10-28 | 2000-05-09 | Sumitomo Bakelite Co Ltd | Polybenzoxazole precursor and resin |
US6297351B1 (en) | 1998-12-17 | 2001-10-02 | Sumitomo Bakelite Company Limited | Polybenzoxazole resin and precursor thereof |
-
1986
- 1986-06-20 JP JP61142871A patent/JPH0755984B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JPS63318A (en) | 1988-01-05 |
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