JPH0442422B2 - - Google Patents

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Publication number
JPH0442422B2
JPH0442422B2 JP59192588A JP19258884A JPH0442422B2 JP H0442422 B2 JPH0442422 B2 JP H0442422B2 JP 59192588 A JP59192588 A JP 59192588A JP 19258884 A JP19258884 A JP 19258884A JP H0442422 B2 JPH0442422 B2 JP H0442422B2
Authority
JP
Japan
Prior art keywords
resin composition
formula
reinforcing material
fibrous reinforcing
weight
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
Application number
JP59192588A
Other languages
Japanese (ja)
Other versions
JPS6172056A (en
Inventor
Shigeru Matsuo
Tomoyoshi Murakami
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.)
Idemitsu Kosan Co Ltd
Original Assignee
Idemitsu Kosan Co Ltd
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 Idemitsu Kosan Co Ltd filed Critical Idemitsu Kosan Co Ltd
Priority to JP19258884A priority Critical patent/JPS6172056A/en
Publication of JPS6172056A publication Critical patent/JPS6172056A/en
Publication of JPH0442422B2 publication Critical patent/JPH0442422B2/ja
Granted legal-status Critical Current

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  • Compositions Of Macromolecular Compounds (AREA)
  • Polyethers (AREA)

Description

【発明の詳細な説明】[Detailed description of the invention]

〔発明の技術分野〕 本発明は、耐熱性ならびに機械的強度に優れた
樹脂組成物に関する。 〔発明の技術的背景とその問題点〕 シアノアリールエーテル系重合体からなる樹脂
は、耐熱性ならびに機械的強度に優れていると同
時に、難燃性、耐溶剤性も良好であるため、種々
の用途に用いられている。しかし、近年、かかる
樹脂の用途範囲が更に広がるにつれて、従来より
も一段と高い耐熱性および機械的強度を要求され
る場合が少なくない。 そこで、更に優れた耐熱性ならびに機械的強度
を備えた樹脂材料の開発への要請が強い。 〔発明の目的〕 本発明はこの要請に応え、シアノアリールエー
テル系重合体を樹脂骨格として含有し、耐熱性な
らびに機械的強度の優れた樹脂組成物の提供を目
的とする。 〔発明の概要〕 本発明の樹脂組成物は、 次式(): (式中、Arは
[Technical Field of the Invention] The present invention relates to a resin composition having excellent heat resistance and mechanical strength. [Technical background of the invention and its problems] Resins made of cyanoaryl ether polymers have excellent heat resistance and mechanical strength, as well as good flame retardancy and solvent resistance. It is used for a purpose. However, in recent years, as the range of uses of such resins has expanded further, even higher heat resistance and mechanical strength are often required than in the past. Therefore, there is a strong demand for the development of resin materials with even better heat resistance and mechanical strength. [Object of the Invention] In response to this demand, the present invention aims to provide a resin composition containing a cyanoaryl ether polymer as a resin skeleton and having excellent heat resistance and mechanical strength. [Summary of the Invention] The resin composition of the present invention has the following formula (): (In the formula, Ar is

【式】または[expression] or

〔発明の実施例〕[Embodiments of the invention]

実施例 1 (1) シアノアリールエーテル系重合体の製造 撹拌装置、精留装置およびアルゴンガス吹込管
を備えた内容積1のセパラブルフラスコに、
2,6−ジクロロベンゾニトリル34.4g(0.2モ
ル)と、ハイドロキノン21.58g(0.196モル)、
スルホラン400ml、トルエン100mlおよび炭酸カリ
ウム30.4g(0.22モル)を仕込み、アルゴンガス
を吹込みながら160℃において1.5時間、190℃に
おいて3.5時間撹拌しながら反応をおこなつた。
反応期間中に生成した水は、絶えずトルエンとと
もに留去した。反応終了後、生成物を室温まで冷
却してメタノール中に投入し、析出した重合体を
ワーニング社製ブレンダーで粉砕し、ついで熱水
2、メタノール2でそれぞれ洗浄することに
より、下記の式()で示されるシアノアリール
エーテル系重合体41.4g(収率100%)を得た。 この重合体をp−クロロフエノールに溶解させ
てその濃度を0.2g/dlとしたときの還元粘度
〔ηSP/C〕は60℃において1.46dl/gであつた。 (2) 樹脂組成物の製造 上記(1)で得られたシアノアリールエーテル系重
合体の粉末に、繊維質強化材として全長3mmの炭
素繊維をその含有量が10重量%となるよう配合
し、押出機により400℃において溶融混練してペ
レツト化した。このペレツトを射出成形して試験
片を作製した。つぎに、この試験片を200℃にお
いて2時間アニーリングした後、熱的性質の測定
および引張試験〔島津製作所製:オートグラフIS
−5000を用い、引張速度1mm/mmとした〕をおこ
ない引張弾性率、破断強度、破断伸びをそれぞれ
測定した。結果を第1表に示した。 実施例 2および3 炭素繊維の含有量をそれぞれ20重量%および30
重量%としたほかは上記実施例1と同様にして樹
脂組成物を製造し、得られた樹脂組成物に対して
実施例1と同様の各試験を行つた。その結果を第
1表に併記した。 実施例 4〜6 繊維質強化材として炭素繊維に代えて、全長3
mmのガラス繊維を使用し、その含有量をそれぞれ
10、20および30重量%としたほかは、上記実施例
1と同様にして樹脂組成物を製造し、得られた樹
脂組成物に対して実施例1と同様の各試験を行つ
た。結果を第1表に併記した。 比較例 1 上記式()で示されるシアノアリールエーテ
ル系重合体に、繊維質強化材を全く配合せずに試
験片を製作し、これにつき実施例1と同様の各試
験を行つた。結果を第1表に示した。
Example 1 (1) Production of cyanoaryl ether polymer In a separable flask with an internal volume of 1 equipped with a stirring device, a rectification device, and an argon gas blowing tube,
34.4 g (0.2 mol) of 2,6-dichlorobenzonitrile, 21.58 g (0.196 mol) of hydroquinone,
400 ml of sulfolane, 100 ml of toluene, and 30.4 g (0.22 mol) of potassium carbonate were charged, and the reaction was carried out with stirring at 160° C. for 1.5 hours and at 190° C. for 3.5 hours while blowing argon gas.
The water produced during the reaction was constantly distilled off along with the toluene. After the reaction is complete, the product is cooled to room temperature and poured into methanol, and the precipitated polymer is pulverized with a Warning blender, and then washed with 2 parts of hot water and 2 parts of methanol, to obtain the following formula () 41.4 g (yield: 100%) of a cyanoaryl ether polymer represented by the following formula was obtained. When this polymer was dissolved in p-chlorophenol to a concentration of 0.2 g/dl, the reduced viscosity [ηSP/C] was 1.46 dl/g at 60°C. (2) Production of resin composition Carbon fibers with a total length of 3 mm are blended as a fibrous reinforcing material into the cyanoaryl ether polymer powder obtained in (1) above so that the content thereof is 10% by weight, The mixture was melt-kneaded using an extruder at 400°C to form pellets. This pellet was injection molded to prepare a test piece. Next, this test piece was annealed at 200°C for 2 hours, and then thermal properties were measured and a tensile test [Shimadzu Corporation: Autograph IS
-5000 at a tensile speed of 1 mm/mm], and the tensile modulus, strength at break, and elongation at break were measured. The results are shown in Table 1. Examples 2 and 3 The carbon fiber content was 20% and 30% by weight, respectively.
A resin composition was produced in the same manner as in Example 1 above, except that the weight % was changed, and the same tests as in Example 1 were conducted on the obtained resin composition. The results are also listed in Table 1. Examples 4 to 6 Instead of carbon fiber as the fibrous reinforcement material, total length 3
mm glass fiber is used, and its content is
A resin composition was produced in the same manner as in Example 1, except that the amounts were 10, 20, and 30% by weight, and the same tests as in Example 1 were conducted on the resulting resin composition. The results are also listed in Table 1. Comparative Example 1 A test piece was prepared by adding no fibrous reinforcing material to the cyanoaryl ether polymer represented by the above formula (), and the same tests as in Example 1 were conducted on the test piece. The results are shown in Table 1.

【表】 実施例 7 (1) シアノアリールエーテル系重合体の製造 実施例1と同様な500mlのセパラブルフラスコ
に、2,6−ジフルオロベンゾニトリル20.88g
(0.15モル)と、4,4′−ビフエノール27.9g
(0.15モル)、クロロベンゼン30ml、スルホラン
120mlを仕込み、アルゴンガスを吹込みながら撹
拌し、200℃に昇温して炭酸カリウム21.15g
(0.15モル)を加えた。ついで、25℃において1
時間、280℃において0.5時間反応させた。この反
応時に生成した水はクロロベンゼンとともに留去
した。反応終了後、冷却して、メタノール中に投
入して重合体を回収し、ワーニング社製ブレンダ
ーで粉砕し、熱水2、メタノール2でそれぞ
れ洗浄して、下記の式(V)で示されるシアノアリー
ルエーテル系重合体42.9g(収率100%)を得た。 この重合体の0.2g/dl濃度のp−クロロフエ
ノール溶液の還元粘度〔ηSP/C〕は60℃におい
て1.16dl/gであつた。 (2) 樹脂組成物の製造 上記(1)で得られたシアノアリールエーテル系重
合体の粉末に、繊維質強化材として実施例1で使
用したのと同様の炭素繊維をその含有量が10重量
%となるように配合し、押出機により400℃にお
いて溶融混練してペレツト化した。このペレツト
を射出成形して試験片を作製し200℃で2時間ア
ニーリングしたのち、実施例1と同様にして熱的
性質の測定および引張試験をおこなつた。結果を
第2表に示した。 実施例 8および9 炭素繊維の含有量をそれぞれ20重量%および30
重量%としたほかは実施例7と同様にして樹脂組
成物を製造し、得られたものについて実施例7と
同様の各試験をおこない、結果を第2表に示し
た。 実施例 10〜12 繊維質強化材として炭素繊維に代えて、実施例
4で使用したと同様のガラス繊維を使用し、その
含有量をそれぞれ10、20および30重量%としたほ
かは、上記実施例7と同様にして樹脂組成物を製
造し、得られた樹脂組成物に対して実施例7と同
様の各試験をおこなつた。結果を第2表に併記し
た。 比較例 2 上記式(V)で示されるシアノアリールエーテル系
重合体に、繊維質強化材を全く配合せずに試験片
を製作し、これにつき、実施例7と同様の試験を
おこない、結果を第2表に示した。
[Table] Example 7 (1) Production of cyanoaryl ether polymer In a 500 ml separable flask similar to Example 1, 20.88 g of 2,6-difluorobenzonitrile was added.
(0.15 mol) and 27.9 g of 4,4'-biphenol
(0.15 mol), chlorobenzene 30ml, sulfolane
Pour 120ml, stir while blowing in argon gas, raise the temperature to 200℃, and add 21.15g of potassium carbonate.
(0.15 mol) was added. Then, 1 at 25℃
The reaction was carried out at 280°C for 0.5 hour. Water produced during this reaction was distilled off together with chlorobenzene. After the reaction is completed, the polymer is cooled and poured into methanol to recover, pulverized in a Warning blender, washed with 2 parts of hot water and 2 parts of methanol, respectively, to obtain a cyano compound represented by the following formula (V). 42.9 g (yield: 100%) of an aryl ether polymer was obtained. The reduced viscosity [ηSP/C] of a p-chlorophenol solution of this polymer at a concentration of 0.2 g/dl was 1.16 dl/g at 60°C. (2) Production of resin composition Carbon fiber similar to that used in Example 1 was added to the cyanoaryl ether polymer powder obtained in (1) above to a content of 10% by weight as a fibrous reinforcing material. % and melt-kneaded using an extruder at 400°C to form pellets. This pellet was injection molded to prepare a test piece, which was annealed at 200° C. for 2 hours, and then measured for thermal properties and subjected to a tensile test in the same manner as in Example 1. The results are shown in Table 2. Examples 8 and 9 Carbon fiber content was 20% and 30% by weight, respectively.
A resin composition was produced in the same manner as in Example 7 except that the weight % was used, and the same tests as in Example 7 were conducted on the obtained composition, and the results are shown in Table 2. Examples 10 to 12 The same procedure as above was carried out except that the same glass fiber as used in Example 4 was used instead of carbon fiber as the fibrous reinforcing material, and the content was 10, 20, and 30% by weight, respectively. A resin composition was produced in the same manner as in Example 7, and the same tests as in Example 7 were conducted on the resulting resin composition. The results are also listed in Table 2. Comparative Example 2 A test piece was prepared by adding no fibrous reinforcing material to the cyanoaryl ether polymer represented by the above formula (V), and the same test as in Example 7 was conducted on it. It is shown in Table 2.

〔発明の効果〕〔Effect of the invention〕

以上の説明から明らかなように、本発明の樹脂
組成物はシアノアリールエーテル系重合体に繊維
質強化材を適正量配合することにより、従来のも
のに比べて耐熱性、機械的強度が共に向上したの
で、電子・電気機器、各種の機械材料など、高い
耐熱性並びに機械的強度の要求される分野におい
て有用である。
As is clear from the above explanation, the resin composition of the present invention has improved heat resistance and mechanical strength compared to conventional compositions by blending an appropriate amount of fibrous reinforcing material with the cyanoaryl ether polymer. Therefore, it is useful in fields that require high heat resistance and mechanical strength, such as electronic and electrical equipment and various mechanical materials.

Claims (1)

【特許請求の範囲】 1 次式(): (式中、Arは【式】または 【式】を表す) で示される繰り返し単位からなり、p−クロロフ
エノールを溶媒とした0.2g/dl濃度の溶液の60
℃における還元粘度[ηsp/c]が0.3dl/g以上
であるシアノアリールエーテル系結晶性重合体
と、該重合体に1〜70重量%の分散された繊維質
強化材とからなることを特徴とする樹脂組成物。 2 該繊維質強化材がガラス繊維または炭素繊維
である特許請求の範囲第1項記載の樹脂組成物。
[Claims] Primary formula (): (In the formula, Ar represents [Formula] or [Formula]) Consisting of the repeating unit shown by
It is characterized by consisting of a cyanoaryl ether-based crystalline polymer having a reduced viscosity [ηsp/c] of 0.3 dl/g or more at °C, and a fibrous reinforcing material dispersed in the polymer in an amount of 1 to 70% by weight. A resin composition. 2. The resin composition according to claim 1, wherein the fibrous reinforcing material is glass fiber or carbon fiber.
JP19258884A 1984-09-17 1984-09-17 Resin composition Granted JPS6172056A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP19258884A JPS6172056A (en) 1984-09-17 1984-09-17 Resin composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP19258884A JPS6172056A (en) 1984-09-17 1984-09-17 Resin composition

Publications (2)

Publication Number Publication Date
JPS6172056A JPS6172056A (en) 1986-04-14
JPH0442422B2 true JPH0442422B2 (en) 1992-07-13

Family

ID=16293774

Family Applications (1)

Application Number Title Priority Date Filing Date
JP19258884A Granted JPS6172056A (en) 1984-09-17 1984-09-17 Resin composition

Country Status (1)

Country Link
JP (1) JPS6172056A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01178552A (en) * 1988-01-07 1989-07-14 Idemitsu Kosan Co Ltd Heat-resistant resin composition
JP2623281B2 (en) * 1988-02-08 1997-06-25 出光興産株式会社 Polymer positive temperature characteristic composition and device
US20250206880A1 (en) * 2022-03-30 2025-06-26 Honshu Chemical Industry Co., Ltd. Polyether nitrile molding material, method for producing the same, and method for producing polyether nitrile resin composition molding material

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2834305A1 (en) * 1978-08-03 1980-02-14 Aeg Elotherm Gmbh Electromagnetic stirrer for molten metal in continuous casting plant - where magnet cores and coils can be adjusted radially to suit shape and size of cast billet

Also Published As

Publication number Publication date
JPS6172056A (en) 1986-04-14

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