JPH03292365A - Resin composition - Google Patents

Resin composition

Info

Publication number
JPH03292365A
JPH03292365A JP9406690A JP9406690A JPH03292365A JP H03292365 A JPH03292365 A JP H03292365A JP 9406690 A JP9406690 A JP 9406690A JP 9406690 A JP9406690 A JP 9406690A JP H03292365 A JPH03292365 A JP H03292365A
Authority
JP
Japan
Prior art keywords
group
resin
aromatic
parts
polyimide resin
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
Application number
JP9406690A
Other languages
Japanese (ja)
Inventor
Yoshihisa Goto
善久 後藤
Masami Amano
正己 天野
Toshiaki Takahashi
敏明 高橋
Hiroyasu Ochi
広泰 大地
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsui Toatsu Chemicals Inc
Original Assignee
Mitsui Toatsu Chemicals Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Mitsui Toatsu Chemicals Inc filed Critical Mitsui Toatsu Chemicals Inc
Priority to JP9406690A priority Critical patent/JPH03292365A/en
Publication of JPH03292365A publication Critical patent/JPH03292365A/en
Pending legal-status Critical Current

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  • Compositions Of Macromolecular Compounds (AREA)

Abstract

PURPOSE:To obtain a resin composition improved in sliding properties by mixing a specific polyimide resin with a fluororesin and an aromatic polyamide resin. CONSTITUTION:100 pts.wt. polyimide resin having repeating units of formula I (wherein X is a direct bond, a divalent 1-10C hydrocarbon group, hexafluorinated isopropylidene, carbonyl, thio, or sulfonyl; and R is a tetravalent group selected from the group consisting of 2C or higher aliphatic groups, cyclic aliphatic groups, monocyclic aromatic groups, condensed polycyclic aromatic group, and non-condensed polycyclic aromatic groups wherein aromatic groups are mutually bonded directly or via crosslinking members) is mixed with 3-60 pts.wt. fluororesin (especially tetrafluoroethylene resin is preferred) and 3-60 pts.wt. aromatic polyamide resin (e.g. a resin having a structure of formula II). A polyimide resin composition is obtained which is remarkably improved in sliding properties such as self-lubricating properties and wear resistance.

Description

【発明の詳細な説明】 本発明は優れた摺動特性を有するポリイミド樹脂組成物
に関する。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a polyimide resin composition having excellent sliding properties.

[従来の技術] ポリイミド樹脂は機械的、化学的、摺動特性および熱的
性質に優れたエンジニアリングプラスチノクであること
より、電気・電子機器、機械、自動車等の用途に種々使
用されている。
[Prior Art] Polyimide resin is an engineering plastic with excellent mechanical, chemical, sliding properties, and thermal properties, and is therefore used in a variety of applications such as electrical and electronic equipment, machinery, and automobiles.

しかし最近の技術の進歩により、ポリイミド樹脂が有す
る特性、特に摺動特性を一段と高めたものが要求される
ようになってきた。ポリイミド樹脂はこのような耐熱性
を活かした摺動部材への適用が考えられているが、ポリ
イミド樹脂単独では自己潤滑性および耐摩耗性の点で十
分でない。
However, with recent advances in technology, there has been a demand for polyimide resins with even higher properties, especially sliding properties. Polyimide resins are considered to be applied to sliding members that take advantage of their heat resistance, but polyimide resins alone do not have sufficient self-lubricating properties and wear resistance.

一般にプラスチックの自己潤滑性、耐摩耗性などの摺動
特性の向上方法としては、固体潤滑剤の配合、四フッ化
エチレン樹脂の配合、潤滑油の配合等が知られており、
例えば特開昭56−61458号公報、特開昭55−1
35163号公報、特公昭47−42615号公報、特
公昭46−5321号公報などにその技術が開示されて
いる。しかし固体潤滑剤を配合したものは耐荷重性の向
上はほとんど期待できない。また四フン化エチレン樹脂
など低摩擦係数を有する樹脂を配合したものは自己潤滑
性の向上には相当の効果が期待できる反面、成形物の機
械的強度ならびに耐荷重性の低下は免れず、耐摩耗性も
十分でない。さらに潤滑油を分散含有させたものにおい
ても他の物体に接着させたり、被着させて使用するよう
な場合には含油性であるために、かえって悪影響を及ぼ
すことがある。
In general, methods for improving the sliding properties such as self-lubricating properties and wear resistance of plastics include blending solid lubricants, blending tetrafluoroethylene resin, blending lubricating oil, etc.
For example, JP-A-56-61458, JP-A-55-1
The technique is disclosed in Japanese Patent Publication No. 35163, Japanese Patent Publication No. 47-42615, Japanese Patent Publication No. 5321-1974, and the like. However, when a solid lubricant is added, hardly any improvement in load resistance can be expected. In addition, products containing resins with a low coefficient of friction such as tetrafluoroethylene resin can be expected to have a considerable effect on improving self-lubricity, but on the other hand, the mechanical strength and load bearing capacity of the molded product will inevitably decrease, and the Abrasion resistance is also not sufficient. Furthermore, even if lubricating oil is dispersed therein, if it is used by adhering or coating it on other objects, it may have an adverse effect because it is oil-impregnated.

〔発明が解決しようとする問題点〕[Problem that the invention seeks to solve]

本発明の目的は、ポリイミド樹脂の摺動特性を改良した
樹脂組成物を提供することにある。
An object of the present invention is to provide a resin composition with improved sliding properties of polyimide resin.

〔問題点を解決するための手段〕[Means for solving problems]

本発明者らは前記の目的を達成するために、鋭意検討し
た結果、フッ素樹脂と共に芳香族ポリアミド樹脂を配合
することに自己潤滑性、耐摩耗性などの摺動特性が顕著
に改良されることを見出し本発明に到達した。
In order to achieve the above object, the inventors of the present invention have made extensive studies and found that mixing an aromatic polyamide resin with a fluororesin significantly improves sliding properties such as self-lubricating properties and wear resistance. This discovery led to the present invention.

すなわち、本発明の樹脂組成物は、ポリイミド樹脂10
0重量部とフッ素樹脂3〜60重量部および芳香族ポリ
アミド樹脂3〜6帽1部からなることを特徴とする。
That is, the resin composition of the present invention comprises polyimide resin 10
0 parts by weight, 3 to 60 parts by weight of fluororesin, and 1 part of aromatic polyamide resin to 3 to 6 parts.

本発明で用いられるポリイミド樹脂は式(I)で表され
る繰り返し単位を有する熱可塑性樹脂である。
The polyimide resin used in the present invention is a thermoplastic resin having a repeating unit represented by formula (I).

(式中、χは直接結合、炭素数1ないし10の2価の炭
化水素基、六)・ン素化されたイソプロピリデン基、カ
ルボニル基、チオ基およびスルホニル基からなる群より
選ばれた基を表す、、Rは炭素数2以上の脂肪族基、環
式脂肪族基、単環式芳香族基、縮合多環式芳香族基、芳
香族基が直接または架橋員より相互に連結された非縮合
多環式芳香族基からなる群より選ばれた4価の基を表す
。)上記ポリイミド樹脂は、式(II)に示すエーテル
ジアミンと式(III)に示す1種以上のテトラカルボ
ン酸二無水物とを通常公知の方法によって容易に製造出
来る。
(In the formula, χ is a direct bond, a divalent hydrocarbon group having 1 to 10 carbon atoms, 6), a group selected from the group consisting of a nitrogen-substituted isopropylidene group, a carbonyl group, a thio group, and a sulfonyl group. , R is an aliphatic group having 2 or more carbon atoms, a cycloaliphatic group, a monocyclic aromatic group, a fused polycyclic aromatic group, or an aromatic group in which the aromatic groups are connected to each other directly or through a bridge member. Represents a tetravalent group selected from the group consisting of non-fused polycyclic aromatic groups. ) The above polyimide resin can be easily produced by a commonly known method using an ether diamine represented by formula (II) and one or more tetracarboxylic dianhydrides represented by formula (III).

(式中、Xは前述と同様である。) (式中、Rは前述と同様である。) 本発明において用いられるフン素樹脂とは分子中にフッ
素原子(F)を含有する合成高分子のことであり、一般
に他の合成樹脂と比較して耐熱性、耐薬品性、電気特性
特に高周波特性に優れまた特有の低摩擦特性、非粘着性
をそなえている。
(In the formula, X is the same as above.) (In the formula, R is the same as above.) The fluororesin used in the present invention is a synthetic polymer containing fluorine atoms (F) in the molecule. Generally, compared to other synthetic resins, it has excellent heat resistance, chemical resistance, electrical properties, especially high frequency properties, and has unique low friction properties and non-stick properties.

代表的な例として、下記(1)〜(9)であられされる
ものが挙げられ、少なくともこれらの1種または2種以
上の混合物が用いられる。
Typical examples include the following (1) to (9), and at least one or a mixture of two or more of these may be used.

(1)十CF2CFZ÷:ポリテトラフルオロエチレン
(PTFE) (2) +CFzCF2CF(CFz)CFz÷:四ツ
、化エチレン六フッ化プロピレン共重合樹脂(FEP)
(3) + (CFzCFz+−+CF (OR) C
Fz)+ : 四7 ノ化エチレンーパーフロロアルキ
ルビニルエーテル共重合樹脂(PFA) (4)+CF2CF2  CF(Ch)Ch C:F(
OR)CFz÷:四フッ化エチレン−へキサフルオロプ
ロピレンパーフルオロアルキルビニルエーテル共重合樹
脂(EPE)(但しRはフッ化アルキル基CnF2n 
+1を示す。) (5) 千GHzC1(zcFzcFz +:四フッ化
エチレンーエチレン共重合樹脂(ETFE) (6) +C)lzcHzcFcIcF2+ ’三フッ
化塩化エチレン樹脂(ECTFE) (7) + CFzCHz +: 77化ビニリデン樹
脂(PVDF)(8) + CFCICF2−3− :
ポリクロロトリフルオロエチレン(PCTFE) (9)÷CH,C肝÷:ポリビニルフルオライド(PV
F)上記したフッ素樹脂の中でも完全にフン素化されて
いる四フッ化エチレン樹脂(PTFE)はこれらの性質
が特に優れているので、本発明では最も好ましく用いら
れる。本発明におけるこれ等フッ素樹脂の添加量は、前
記したポリイミド樹脂100重量部に対し3〜60重量
部の範囲である。フン素樹脂の添加量が3重量部より少
ない場合は、得られる樹脂組成物の自己潤滑性改良効果
が小さく好ましくない。またフン素樹脂の添加量が60
重量部より多い場合には、得られる樹脂組成物の機械的
特性、成形加工性が悪くなり好ましくない。好ましい添
加量は10〜50重量部である。また本発明で併用され
る芳香族ポリアミド樹脂は、比較的新しく開発された耐
熱性樹脂であり、多くの特異な特性を活かして各分野へ
の展開が期待されている。例えば代表的な例として次の
様な構造式のものが挙げられ、少なくともこれらの1種
または2種以上の混合物が用いられる。
(1) 10 CF2CFZ÷: polytetrafluoroethylene (PTFE) (2) +CFzCF2CF (CFz) CFz÷: 4, ethylene hexafluorinated propylene copolymer resin (FEP)
(3) + (CFzCFz+-+CF (OR) C
Fz)+: 47 ethylene perfluoroalkyl vinyl ether copolymer resin (PFA) (4)+CF2CF2 CF(Ch)Ch C:F(
OR) CFz÷: Tetrafluoroethylene-hexafluoropropylene perfluoroalkyl vinyl ether copolymer resin (EPE) (R is a fluorinated alkyl group CnF2n
Indicates +1. ) (5) 1,000 GHzC1 (zcFzcFz +: Tetrafluoroethylene-ethylene copolymer resin (ETFE) (6) +C) lzcHzcFcIcF2+ 'Trifluorochloroethylene resin (ECTFE) (7) + CFzCHz +: Vinylidene 77ide resin ( PVDF) (8) + CFCICF2-3-:
Polychlorotrifluoroethylene (PCTFE) (9) ÷ CH, C liver ÷: polyvinyl fluoride (PV
F) Among the above-mentioned fluororesins, completely fluorinated tetrafluoroethylene resin (PTFE) has particularly excellent properties and is therefore most preferably used in the present invention. The amount of these fluororesins added in the present invention is in the range of 3 to 60 parts by weight per 100 parts by weight of the above-mentioned polyimide resin. If the amount of the fluorine resin added is less than 3 parts by weight, the effect of improving the self-lubricity of the resulting resin composition will be small, which is not preferable. In addition, the amount of fluorine resin added is 60
If the amount is more than 1 part by weight, the resulting resin composition will have poor mechanical properties and moldability, which is not preferable. The preferred amount added is 10 to 50 parts by weight. Further, the aromatic polyamide resin used in combination in the present invention is a relatively newly developed heat-resistant resin, and is expected to be used in various fields by taking advantage of its many unique properties. For example, typical examples include those having the following structural formulas, and at least one kind or a mixture of two or more of these can be used.

例)デュポン社商品名”Keylar 例)デュポン社商品名″Nomex 帝   大府品名″Coneχ その他オルト、メタ、パラ位の異性構造により各種骨格
の芳香族ポリアミド樹脂が与えられるが中でも(1)の
バラ位−バラ位結合のものは軟化点および融点が非常に
高く耐熱性樹脂として本発明では最も好ましく用いられ
る。本発明における芳香族ポリアミド樹脂の添加量は、
前記したポリイミド樹脂100重量部に対し3〜60重
量部の範囲である。芳香族ポリアミド樹脂の添加量が3
重量部より少ない場合は得られる樹脂組成物の耐摩耗性
改良効果が小さく、また添加量が60重量部より多い場
合には得られる樹脂組成物の機械的特性、成形加工性が
悪くなり好ましくない。好ましい添加量は10〜50重
量部である。
Example) DuPont product name "Keylar" Example) DuPont product name "Nomex" Product name "Coneχ Other than that, aromatic polyamide resins with various skeletons are given by the isomeric structure at the ortho, meta, and para positions, but among them, the (1) position is - The one with a bond at the distal position has a very high softening point and melting point, and is most preferably used in the present invention as a heat-resistant resin.The amount of aromatic polyamide resin added in the present invention is as follows:
The amount is in the range of 3 to 60 parts by weight based on 100 parts by weight of the polyimide resin described above. Addition amount of aromatic polyamide resin is 3
If the amount is less than 60 parts by weight, the effect of improving the wear resistance of the resulting resin composition will be small, and if the amount added is more than 60 parts by weight, the mechanical properties and moldability of the resulting resin composition will deteriorate, which is undesirable. . The preferred amount added is 10 to 50 parts by weight.

また得られる樹脂組成物の機械的特性、成形加工性の点
より、フッ素樹脂と芳香族ポリアミド樹脂の添加量の合
計は、ポリイミド樹脂100重量部に対し100重量部
以下であることがより好ましい。本発明の樹脂組成物に
はさらに本発明の目的を損なわない範囲で繊維状強化材
(例えば炭素繊維、ガラス繊維など)、粒状強化材(例
えば炭酸カルシウム、タルク、シリカなど)および顔料
などの通常の添加材を添加することが出来る。
Further, from the viewpoint of mechanical properties and moldability of the resulting resin composition, it is more preferable that the total amount of the fluororesin and aromatic polyamide resin added is 100 parts by weight or less based on 100 parts by weight of the polyimide resin. The resin composition of the present invention may further contain conventional materials such as fibrous reinforcing materials (e.g., carbon fibers, glass fibers, etc.), granular reinforcing materials (e.g., calcium carbonate, talc, silica, etc.), and pigments, to the extent that the objects of the present invention are not impaired. Additives can be added.

本発明のポリイミド樹脂へのフッ素樹脂および芳香族ポ
リアミド樹脂の添加方法には特に制限はなく種々の手法
が採用可能であるが、各々を別々に、あるいは予め三者
をヘンシェルミキサー等で混合した後、押出機に供給し
溶融混練しベレットに押出す方法が一般に行われる。こ
のようにして得られた本発明の潤滑性の樹脂組成物は、
射出成形、押出成形、圧縮成形等の成形方法により任意
の成形品に成形することが出来る。成形品は優れた摺動
特性を示し各種摺動部品、例えば各種軸受、ピストンリ
ング、ギア、カム、スライダー、各種バルブ部品に用い
られる。
There are no particular restrictions on the method of adding the fluororesin and aromatic polyamide resin to the polyimide resin of the present invention, and various methods can be adopted. A commonly used method is to supply the material to an extruder, melt-knead it, and extrude it into pellets. The lubricating resin composition of the present invention thus obtained is
It can be molded into any desired molded product by a molding method such as injection molding, extrusion molding, or compression molding. Molded products exhibit excellent sliding properties and are used for various sliding parts, such as various bearings, piston rings, gears, cams, sliders, and various valve parts.

(実施例) 以下、実施例および比較例により、詳細に本発明を説明
する。
(Examples) Hereinafter, the present invention will be explained in detail with reference to Examples and Comparative Examples.

なお、対数粘度は、以下のような手法により測定した。Note that the logarithmic viscosity was measured by the following method.

対数粘度;ポリイミド樹脂粉末0.5gをp−クロロフ
ェノール/フェノール(重量比9/1)の混合溶媒10
0戚に加熱溶解した後、35°Cに冷却し測定した。
Logarithmic viscosity: 10 g of polyimide resin powder mixed with p-chlorophenol/phenol (9/1 weight ratio)
After heating and dissolving the solution in 0-alpha, it was cooled to 35°C and measured.

実施例1 4.4−ビス(3−アミノフェノキシ)ビフェニルとピ
ロメリット酸二無水物を原料として得られたポリイミド
樹脂粉末(対数粘度0.45dl/ g )、フッ素樹
脂としてダイキン社製四フッ化エチレン樹脂、商品名L
−5、芳香族ポリアミド樹脂としてデュポン社製芳香族
ポリアミド樹脂繊維、商品名KEVLAR49をそれぞ
れ表−1に記載の組成でトライブレンドとした後、2軸
押比機(口径30胴)によりシリンダー温度400〜4
1°Cで押出し、均一なベレ・ントを得た。
Example 1 Polyimide resin powder (logarithmic viscosity 0.45 dl/g) obtained using 4.4-bis(3-aminophenoxy)biphenyl and pyromellitic dianhydride as raw materials, and Daikin tetrafluoride resin as the fluororesin. Ethylene resin, trade name L
-5. As the aromatic polyamide resin, aromatic polyamide resin fiber manufactured by DuPont, trade name KEVLAR 49, was made into a tri-blend with the composition shown in Table-1, and then a cylinder temperature of 400 ~4
Extrusion was performed at 1°C to obtain a uniform bead.

このベレットを射出成形機によりシリンダー温度400
〜420°C2金型温度200℃の条件で試験片を成形
し、摺動特性を測定したところ表−Iの結果が得られた
This pellet is molded using an injection molding machine at a cylinder temperature of 400 m
A test piece was molded at a mold temperature of 200°C to 420°C, and the sliding properties were measured, and the results shown in Table I were obtained.

なお摩擦係数は、相手材をステンレススチスールとし、
面圧10kg/c−d、速度10cIII/secの条
件でスラスト式摩耗試験機を用いて、室温で測定した。
The coefficient of friction is calculated using stainless steel as the mating material.
Measurements were made at room temperature using a thrust type abrasion tester under the conditions of a surface pressure of 10 kg/c-d and a speed of 10 cIII/sec.

限界Pv値は、スラスト式摩耗試験機を用い面圧、速度
を変化させ樹脂試験片が軟化し摩擦係数が急激に上昇し
た時のPと■との積で示した。さらに摩耗係数は、相手
材をステンレススチスールとして面圧5kg/cIf1
.速度100m/mimの条件で、円筒式摩耗試験機を
用い室温で測定した。
The limit Pv value was expressed as the product of P and ■ when the resin test piece softened and the friction coefficient sharply increased by changing the surface pressure and speed using a thrust type abrasion tester. Furthermore, the wear coefficient is 5kg/cIf1 when the mating material is stainless steel.
.. Measurements were made at room temperature using a cylindrical abrasion tester at a speed of 100 m/min.

[発明の効果] 本発明の樹脂組成物は、 擦特性を有している。[Effect of the invention] The resin composition of the present invention is It has rubbing properties.

優れた耐摩耗性及び摩Excellent wear resistance and friction

Claims (1)

【特許請求の範囲】[Claims] (1)式( I )で表される繰り返し単位を有するポリ
イミド樹脂100重量部に対し、フッ素樹脂3〜60重
量部および芳香族ポリアミド樹脂3〜60重量部を含む
ことを特徴とするポリイミド樹脂組成物。 ( I )▲数式、化学式、表等があります▼ (式中、Xは直接結合、炭素数1ないし10の2価の炭
化水素基、六フッ素化されたイソプロピリデン基、カル
ボニル基、チオ基およびスルホニル基からなる群より選
ばれた基を表す。Rは炭素数2以上の脂肪族基、環式脂
肪族基、単環式芳香族基、縮合多環式芳香族基、芳香族
基が直接または架橋員より相互に連結された非縮合多環
式芳香族基からなる群より選ばれた4価の基を表す。)
(1) A polyimide resin composition comprising 3 to 60 parts by weight of a fluororesin and 3 to 60 parts by weight of an aromatic polyamide resin based on 100 parts by weight of a polyimide resin having a repeating unit represented by formula (I). thing. (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X is a direct bond, a divalent hydrocarbon group having 1 to 10 carbon atoms, a hexafluorinated isopropylidene group, a carbonyl group, a thio group, Represents a group selected from the group consisting of sulfonyl groups.R represents an aliphatic group having 2 or more carbon atoms, a cycloaliphatic group, a monocyclic aromatic group, a fused polycyclic aromatic group, or an aromatic group directly or represents a tetravalent group selected from the group consisting of non-fused polycyclic aromatic groups interconnected by a bridge member.)
JP9406690A 1990-04-11 1990-04-11 Resin composition Pending JPH03292365A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP9406690A JPH03292365A (en) 1990-04-11 1990-04-11 Resin composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP9406690A JPH03292365A (en) 1990-04-11 1990-04-11 Resin composition

Publications (1)

Publication Number Publication Date
JPH03292365A true JPH03292365A (en) 1991-12-24

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Family Applications (1)

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JP9406690A Pending JPH03292365A (en) 1990-04-11 1990-04-11 Resin composition

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08319391A (en) * 1995-05-25 1996-12-03 Nippon Pillar Packing Co Ltd Sliding member
JP2003521644A (en) * 2000-01-31 2003-07-15 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー Polymer bearing with elastomer
KR20170134610A (en) 2015-04-01 2017-12-06 미쓰비시 엔피쯔 가부시키가이샤 Based resin-containing polyimide precursor solution composition, polyimide, polyimide film, adhesive composition for circuit board, and method for manufacturing the same

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59202258A (en) * 1983-04-30 1984-11-16 Mitsui Toatsu Chem Inc Polyether-imide resin composition
JPS62265350A (en) * 1986-05-14 1987-11-18 Mitsui Toatsu Chem Inc Polyimide resin composition
JPS638445A (en) * 1986-06-27 1988-01-14 Idemitsu Petrochem Co Ltd Polyethylene resin composition
JPS638455A (en) * 1986-06-30 1988-01-14 Mitsui Toatsu Chem Inc Polyimide resin composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59202258A (en) * 1983-04-30 1984-11-16 Mitsui Toatsu Chem Inc Polyether-imide resin composition
JPS62265350A (en) * 1986-05-14 1987-11-18 Mitsui Toatsu Chem Inc Polyimide resin composition
JPS638445A (en) * 1986-06-27 1988-01-14 Idemitsu Petrochem Co Ltd Polyethylene resin composition
JPS638455A (en) * 1986-06-30 1988-01-14 Mitsui Toatsu Chem Inc Polyimide resin composition

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08319391A (en) * 1995-05-25 1996-12-03 Nippon Pillar Packing Co Ltd Sliding member
JP2003521644A (en) * 2000-01-31 2003-07-15 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー Polymer bearing with elastomer
JP4880162B2 (en) * 2000-01-31 2012-02-22 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー Polymer bearing with elastomer
KR20170134610A (en) 2015-04-01 2017-12-06 미쓰비시 엔피쯔 가부시키가이샤 Based resin-containing polyimide precursor solution composition, polyimide, polyimide film, adhesive composition for circuit board, and method for manufacturing the same

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