JPH0749484B2 - Thermosetting resin composition - Google Patents
Thermosetting resin compositionInfo
- Publication number
- JPH0749484B2 JPH0749484B2 JP61190563A JP19056386A JPH0749484B2 JP H0749484 B2 JPH0749484 B2 JP H0749484B2 JP 61190563 A JP61190563 A JP 61190563A JP 19056386 A JP19056386 A JP 19056386A JP H0749484 B2 JPH0749484 B2 JP H0749484B2
- Authority
- JP
- Japan
- Prior art keywords
- thermosetting resin
- resin composition
- bismaleimide
- diamine
- flexibility
- 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
Links
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は耐衝撃性と可撓性に優れた新規な熱硬化性樹脂
組成物に関する。The present invention relates to a novel thermosetting resin composition having excellent impact resistance and flexibility.
従来から、イミド構造を有する熱硬化性樹脂は電気絶縁
性、耐熱性、成形品の寸法安定性に優れた性能を有する
為、産業上広く利用されている。BACKGROUND ART Conventionally, a thermosetting resin having an imide structure has been widely used in industry because it has excellent electrical insulation properties, heat resistance, and dimensional stability of molded products.
然しながら、芳香族系ビスマレイミドを使用してなる熱
硬化性樹脂は不溶不融で、しかも耐熱性に優れた素材で
あるが、耐衝撃性及び可撓性に乏しいという欠点があっ
た。However, the thermosetting resin using the aromatic bismaleimide is a material that is insoluble and infusible and has excellent heat resistance, but has a drawback that it is poor in impact resistance and flexibility.
この為、芳香族系ビスマレイミドの耐衝撃性及び可撓性
を改良する方法として、芳香族系ビスマレイミドに芳香
族系ジアミンを使用する試みがある。例えば、N,N′−
（4,4′−メチレンジフェニレン）ビスマレイミドと4,
4′−ジアミノジフェニルメタンとからなるポリアミノ
ビスマレイミド樹脂（ローヌ・プーラン社製、商品名
ケルイミダ）は耐衝撃性及び可撓性が芳香族系ビスマレ
イミド単独のものよりも優れている為、含浸ワニス、積
層板、成形品等に広く用いられている。Therefore, as a method for improving the impact resistance and flexibility of the aromatic bismaleimide, there is an attempt to use an aromatic diamine for the aromatic bismaleimide. For example, N, N′−
(4,4'-methylenediphenylene) bismaleimide and 4,
Polyamino bismaleimide resin consisting of 4'-diaminodiphenylmethane (Rhone Poulenc Company, trade name
Since it is superior in impact resistance and flexibility to the aromatic bismaleimide alone, it is widely used in impregnating varnishes, laminates, molded articles and the like.
しかしながら、これらの熱硬化性樹脂は、未だ耐衝撃性
及び可撓性の面から満足のいくものではなかった。However, these thermosetting resins have not been satisfactory in terms of impact resistance and flexibility.
本発明の目的は、従来の耐熱性を維持し、然も耐衝撃性
及び可撓性に優れた、強靭性を有する熱硬化性樹脂を提
供することにある。It is an object of the present invention to provide a thermosetting resin that maintains conventional heat resistance, is excellent in impact resistance and flexibility, and has toughness.
本発明者らは、前記目的を達成するために鋭意研究を行
った結果、新規なビスマレイミド化合物と特定量のジア
ミン化合物よりなる熱硬化性樹脂組成物が、特に有効で
あることを見出し、本発明を完成させた。As a result of intensive studies to achieve the above objects, the present inventors have found that a thermosetting resin composition comprising a novel bismaleimide compound and a specific amount of a diamine compound is particularly effective, and Completed the invention.
すなわち、本発明の熱硬化性樹脂組成物は、式（Ｉ） で表されるN,N′−4,4′−ジフェニルメタン−ビスマレ
イミドと一般式（II） にて表されるジアミン化合物よりなる熱硬化性樹脂組成
物である。That is, the thermosetting resin composition of the present invention has the formula (I) N, N'-4,4'-diphenylmethane-bismaleimide represented by the general formula (II) A thermosetting resin composition comprising a diamine compound represented by.
前記式（Ｉ）で表わされるN,N′−4,4′−ジフェニルメ
タン−ビスマレイミドは通常公知の方法により、4,4′
−ジアミノジフェニルメタンと無水マレイン酸を縮合・
脱水反応させて、容易に製造できる。The N, N'-4,4'-diphenylmethane-bismaleimide represented by the above formula (I) can be prepared by conventional methods using 4,4 '
-Condensation of diaminodiphenylmethane and maleic anhydride
It can be easily produced by dehydration reaction.
本発明で使用されるジアミン化合物は具体的には、1,3
−ビス（３−アミノフェノキシ）ベンゼン、4,4′−ビ
ス（３−アミノフェノキシ）ビフェニルであり、これら
は単独あるいは二種混合して用いられる。The diamine compound used in the present invention is specifically 1,3
-Bis (3-aminophenoxy) benzene and 4,4'-bis (3-aminophenoxy) biphenyl, which may be used alone or in combination of two kinds.
これらのジアミン化合物は、それぞれ対応するビスフェ
ノール類とｍ−ジニトロベンゼンを非プロトン性極性溶
媒中、塩基の存在下に縮合後、還元することにより高純
度、高収率で工業的に有利に製造できる（特開昭61−22
1158号、特公昭６−727号）。These diamine compounds can be industrially advantageously produced in high purity and high yield by condensing the corresponding bisphenols and m-dinitrobenzene in an aprotic polar solvent in the presence of a base and then reducing the condensation. (JP 61-22
No. 1158, Japanese Patent Publication No. 6-727).
上記式（Ｉ）で表わされるN,N′−4,4′−ジフェニルメ
タン−ビスマレイミドと式（II）で表わされるジアミン
化合物より熱硬化性樹脂組成物を得るが、この場合、以
下に示す各種の方法が使用できる。A thermosetting resin composition is obtained from N, N'-4,4'-diphenylmethane-bismaleimide represented by the above formula (I) and a diamine compound represented by the formula (II). Can be used.
（１）ビスマレイミドとジアミンを固体状で粉砕混合し
たもの、あるいはこれを加熱処理して、プレポリマーと
した後、粉砕してペレット又は粉状にする。この場合の
加熱条件はプレポリマーの段階まで部分硬化させる条件
がよく、一般には70〜220℃の温度で５〜240分、望まし
くは80〜200℃の温度で10〜180分とすることが適当であ
る。(1) Bismaleimide and diamine are pulverized and mixed in a solid state, or this is heat-treated into a prepolymer and then pulverized into pellets or powder. In this case, the heating condition is preferably such that the prepolymer stage is partially cured. Generally, the temperature is 70 to 220 ° C. for 5 to 240 minutes, and the temperature is preferably 80 to 200 ° C. for 10 to 180 minutes. Is.
（２）ビスマレイミドとジアミンを有機溶媒に溶解さ
せ、次いで貧溶媒中に排出し析出してきた結晶をロ過乾
燥してペレット又は粉状とするか、又は有機溶媒に溶解
後、加熱処理によりプレポリマーの段階まで部分硬化さ
せた後、貧溶媒中に排出し析出してきた結晶をロ過乾燥
してペレット又は粉状とする。この場合の条件も（１）
に準ずる。使用可能な有機溶媒としては両成分と実質的
に反応しない溶媒という点で制限を受けるが、このほか
に両反応成分に対する良溶媒であることが望ましい。通
常、用いられる反応溶媒は塩化メチレン、ジクロロエタ
ン、トリクロロエチレンなどのハロゲン化炭化水素、ア
セトン、メチルエチルケトン、シクロヘキサノン、ジイ
ソプロピルケトンなどのケトン類、テトラヒドロフラ
ン、ジオキサン、メチルセロソルブなどのエーテル類、
ベンゼン、トルエン、クロロベンゼンなどの芳香族化合
物、アセトニトリル、N,N−ジメチルホルムアミド、N,N
−ジメチルアセトアミド、ジメチルスルホキシド、Ｎ−
メチル−２−ピロリドン、1,3−ジメチル−２−イミダ
ゾリジノンなどの非プロトン性極性溶媒などである。(2) Bismaleimide and diamine are dissolved in an organic solvent, then discharged into a poor solvent and the precipitated crystals are filtered and dried to give pellets or powder, or after dissolving in an organic solvent, pretreatment by heat treatment is performed. After the polymer is partially cured to the stage, it is discharged into a poor solvent and the precipitated crystals are filtered and dried to obtain pellets or powder. The condition in this case is also (1)
According to. The usable organic solvent is limited in that it does not substantially react with both components, but it is desirable that it is a good solvent for both reaction components. Usually, the reaction solvent used is methylene chloride, dichloroethane, halogenated hydrocarbons such as trichloroethylene, acetone, ketones such as methyl ethyl ketone, cyclohexanone, diisopropyl ketone, tetrahydrofuran, dioxane, ethers such as methyl cellosolve,
Aromatic compounds such as benzene, toluene, chlorobenzene, acetonitrile, N, N-dimethylformamide, N, N
-Dimethylacetamide, dimethyl sulfoxide, N-
Examples include aprotic polar solvents such as methyl-2-pyrrolidone and 1,3-dimethyl-2-imidazolidinone.
なお、本発明によるビスマレイミドとジアミンよりなる
組成物に、本発明の目的をそこなわない範囲で酸化防止
剤および熱安定剤、紫外線吸収剤、難燃助剤、帯電防止
剤、滑剤、着色剤などの通常の添加剤を１種以上添加す
ることができる。In addition, in the composition consisting of bismaleimide and diamine according to the present invention, an antioxidant and a heat stabilizer, an ultraviolet absorber, a flame retardant aid, an antistatic agent, a lubricant, and a colorant within a range that does not impair the object of the present invention. One or more of the usual additives such as can be added.
また、他の熱硬化性樹脂（例えば、フェノール樹脂、エ
ポキシ樹脂など）、熱可塑性樹脂（例えば、ポリエチレ
ン、ポリプロピレン、ポリアミド、ポリカーボネート、
ポリサルサン、ポリエーテルサルサン、ポリエーテルエ
ーテルケトン、変性ポリフェニレンオキシド、ポリフェ
ニレンサルファイドなど）または、ガラス繊維、炭素繊
維、芳香族ポリアミド繊維、アルミナ繊維、チタン酸カ
リウム繊維などの補助材やクレー、マイカ、シリカ、グ
ラファイト、ガラスビーズ、アルミナ、炭酸カルシウム
などの充填材もその目的に応じて適当量を配合すること
も可能である。In addition, other thermosetting resins (for example, phenol resin, epoxy resin, etc.), thermoplastic resins (for example, polyethylene, polypropylene, polyamide, polycarbonate,
Polysarsan, polyether salsan, polyetheretherketone, modified polyphenylene oxide, polyphenylene sulfide, etc.) or auxiliary materials such as glass fiber, carbon fiber, aromatic polyamide fiber, alumina fiber, potassium titanate fiber, clay, mica, silica Fillers such as graphite, glass beads, alumina, and calcium carbonate can also be added in appropriate amounts according to the purpose.
式（１）で表わされるN,N′−4,4′−ジフェニルメタン
−ビスマレイミドと式（II）で表わされるジアミン化合
物の使用割合はモル比10:1〜1:1.2の範囲で使用するの
が好ましい。ジアミン化合物の使用割合が少ないと、硬
化物にした場合、良好な耐衝撃性及び可撓性を有するも
のが得られない。逆に多すぎると硬化物の耐熱性に悪影
響を与える。The N, N'-4,4'-diphenylmethane-bismaleimide represented by the formula (1) and the diamine compound represented by the formula (II) are used in a molar ratio of 10: 1 to 1: 1.2. Is preferred. When the proportion of the diamine compound used is small, a cured product cannot have good impact resistance and flexibility. On the contrary, if the amount is too large, the heat resistance of the cured product is adversely affected.
本発明の熱硬化性樹脂組成物は、圧縮成形法、トランス
ファー成形法、押出成形法、射出成形法等公知の成形法
により成形され実用に供される。The thermosetting resin composition of the present invention is molded by a known molding method such as a compression molding method, a transfer molding method, an extrusion molding method, and an injection molding method, and put into practical use.
以下、本発明を実施例により説明する。 Hereinafter, the present invention will be described with reference to examples.
実施例−１〜４ 撹拌機、還流冷却器および窒素導入管を備えたステンレ
ス製容器に、N,N′−4,4′−ジフェニルメタン−ビスマ
レイミドと4,4′−ビス（３−アミノフェノキシ）ビフ
ェニルを各々表−１に示した仕込みモル比で装入し、18
0℃で20分加熱溶融反応した。その後、室温まで冷却
し、褐色透明なガラス状に固化した反応生成物を砕いて
取り出し、さらに乳鉢で粉砕して60メッシュのフルイに
通し、部分硬化したポリアミノビスマレイミド型熱硬化
性樹脂組成物を得た。Examples-1 to 4 In a stainless steel container equipped with a stirrer, a reflux condenser and a nitrogen inlet tube, N, N'-4,4'-diphenylmethane-bismaleimide and 4,4'-bis (3-aminophenoxy) were added. ) Biphenyl was charged at the charging molar ratio shown in Table 1, and 18
The mixture was melted by heating at 0 ° C for 20 minutes. Then, cooled to room temperature, the reaction product solidified into a brown transparent glass is crushed and taken out, further crushed in a mortar and passed through a 60 mesh sieve, and a partially cured polyamino bismaleimide type thermosetting resin composition is obtained. Obtained.
該組成物を180℃に熱した金型（10×80×4mm）に加熱溶
融させながら、充填した後、圧力50Kg/cm2、200℃で30
分保持し、圧縮成形した。その後室温まで冷却した後、
金型内より一次成形物を取り出し、さらに250℃の熱風
ギャーオーブン中で４時間ポストキュアーして、アイゾ
ット衝撃試験片及び曲げ試験片を得た。アイゾット衝撃
試験（ノッチ無し）はASTMD−256に、曲げ試験はASTMD
−790に準じて行い、合わせて成形試験片の％重量減少
温度を測定したところ表−１の結果を得た。While heating and melting the composition in heated mold to 180 ℃ (10 × 80 × 4mm ), after filling, 30 at a pressure 50Kg / cm 2, 200 ℃
Hold for minutes and compression molding. After cooling to room temperature,
The primary molded product was taken out of the mold and post-cured for 4 hours in a hot air gar oven at 250 ° C. to obtain an Izod impact test piece and a bending test piece. Izod impact test (no notch) is ASTM D-256, bending test is ASTM D-256
It was carried out according to -790, and the% weight loss temperature of the molded test piece was also measured. The results shown in Table 1 were obtained.
実施例−５ 撹拌機、還流冷却器および窒素導入管を備えたステンレ
ス製容器に、N,N′−4,4′−ジフェニルメタン−ビスマ
レイミドと4,4′−ビス（３−アミノフェノキシ）ビフ
ェニルを各々表−１に示した仕込みモル比で装入し、こ
れに樹脂濃度が55重量％になる量のＮ−メチル−２−ピ
ロリドンを注入して、両成分を溶解した後、130℃で50
分間加熱反応した。得られた褐色透明ワニスを撹拌して
いる水中に滴下した後、析出した沈殿をロ過、水洗し、
80℃15時間熱風乾燥した。これを110℃で20分、更に130
℃で20分乾燥した後、乳鉢で粉砕して、60メッシュのフ
ルイに通し、部分硬化したポリアミノビスマレイミド型
熱硬化性樹脂組成物を得た。Example-5 N, N'-4,4'-diphenylmethane-bismaleimide and 4,4'-bis (3-aminophenoxy) biphenyl were placed in a stainless steel container equipped with a stirrer, a reflux condenser and a nitrogen inlet tube. Were charged at the charging molar ratios shown in Table 1, respectively, and N-methyl-2-pyrrolidone in an amount such that the resin concentration became 55% by weight was injected to dissolve both components, and then at 130 ° C. 50
It reacted by heating for a minute. The resulting brown transparent varnish was added dropwise to water with stirring, and the deposited precipitate was filtered and washed with water,
It was dried with hot air at 80 ° C for 15 hours. 20 minutes at 110 ℃, then 130
After drying at 0 ° C for 20 minutes, it was ground in a mortar and passed through a 60-mesh sieve to obtain a partially cured polyamino bismaleimide type thermosetting resin composition.
以下実施例−１〜４と同様の操作をして表−１の結果を
得た。Then, the same operation as in Examples-1 to 4 was performed to obtain the results shown in Table-1.
実施例−６及び比較例−１〜４ 表−１に示したビスマレイミドとジアミンを用いて、表
−１に示した仕込みモル比で実施例−１〜４と同様の操
作をして表−１の結果を得た。Example-6 and Comparative Examples-1 to 4 Using bismaleimide and diamine shown in Table-1, the same operation as in Examples-1 to 4 was carried out at the charged molar ratio shown in Table-1. A result of 1 was obtained.
比較例−５ 攪拌機、還流冷却器および窒素導入管を備えた容器に2,
2−ビス〔４−（３−アミノフェノキシ）フェニル〕プ
ロパン41.0g（0.1モル）とN,N−ジメチルアセトアミド1
88.4gを装入し、窒素雰囲気下において、ピロメリット
酸二無水物21.8g（0.1モル）を溶液温度の上昇に注意し
ながら分割して加え、室温で約20時間かきまぜた。斯く
して得られたポリアミド酸溶液に、3.0gのトリエチルア
ミンおよび3.1gの無水酢酸を約30分かけて添加し、その
後約60分かきまぜた。この溶液に200gのメタノールを加
え、30℃においてポリイミド粉をろ別した。得られたポ
リイミド粉をメタノールおよびアセトンで洗浄したの
ち、窒素雰囲気下に200℃で16時間乾燥して、59.1g（収
率97％）のポリイミド粉を得た。このポリイミド粉を25
0℃に加熱した125×12.5×3.2mmの金型に圧入した後、3
50℃×50kg/cm2×5minで圧縮成形して曲げ試験片を得
た。得られた試験片をASTM Ｄ−638に準じて、室温下
での曲げ強度及び曲げ弾性率を測定し表−１の結果を得
た。Comparative Example-5 A container equipped with a stirrer, a reflux condenser, and a nitrogen inlet tube was provided with 2,
2-bis [4- (3-aminophenoxy) phenyl] propane 41.0 g (0.1 mol) and N, N-dimethylacetamide 1
In a nitrogen atmosphere, 81.8 g was charged, and 21.8 g (0.1 mol) of pyromellitic dianhydride was added in portions while paying attention to the rise in solution temperature, and the mixture was stirred at room temperature for about 20 hours. To the thus obtained polyamic acid solution, 3.0 g of triethylamine and 3.1 g of acetic anhydride were added over about 30 minutes, followed by stirring for about 60 minutes. 200 g of methanol was added to this solution, and the polyimide powder was filtered off at 30 ° C. The obtained polyimide powder was washed with methanol and acetone and then dried at 200 ° C. for 16 hours in a nitrogen atmosphere to obtain 59.1 g (yield 97%) of polyimide powder. 25 of this polyimide powder
After press-fitting into a 125 × 12.5 × 3.2 mm mold heated to 0 ° C, 3
Bending test pieces were obtained by compression molding at 50 ° C. × 50 kg / cm 2 × 5 min. According to ASTM D-638, the obtained test piece was measured for bending strength and bending elastic modulus at room temperature, and the results shown in Table 1 were obtained.
表−１の結果より本発明による熱硬化性樹脂組成物はア
イゾット衝撃値が高く、しかも曲げ強度、曲げ弾性率も
高く、耐衝撃性と可撓性に優れた材料であり、さらに５
％重量減少温度も390℃以上と優れた耐熱性を有してい
る。From the results in Table 1, the thermosetting resin composition according to the present invention is a material having a high Izod impact value, a high bending strength and a high bending elastic modulus, and excellent impact resistance and flexibility.
It also has excellent heat resistance with a% weight loss temperature of 390 ° C or higher.
〔発明の効果〕 本発明の熱硬化性樹脂は優れた耐熱性、耐衝撃性及び可
撓性を有しており、電気、電子部品、各種構造部材、摺
動部品など広くその用途が期待され、産業上の利用効果
は大きい。 [Advantages of the Invention] The thermosetting resin of the present invention has excellent heat resistance, impact resistance and flexibility, and is expected to be widely used for electric, electronic parts, various structural members, sliding parts and the like. The industrial use effect is great.
Claims (2)
イミドと一般式（II） にて表されるジアミン化合物よりなる熱硬化性樹脂組成
物。1. A formula (I) N, N'-4,4'-diphenylmethane-bismaleimide represented by the general formula (II) A thermosetting resin composition comprising a diamine compound represented by.
物（II）をモル比10:1〜1:1.2の範囲の割合で使用する
特許請求の範囲第（１）項記載の熱硬化性樹脂組成物2. A thermosetting resin composition according to claim 1, wherein the bismaleide compound (I) and the diamine compound (II) are used in a molar ratio of 10: 1 to 1: 1.2.
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61190563A JPH0749484B2 (en) | 1986-08-15 | 1986-08-15 | Thermosetting resin composition |
| CA000541494A CA1270998A (en) | 1986-07-15 | 1987-07-07 | Thermosetting resin composition |
| US07/071,161 US4831102A (en) | 1986-07-15 | 1987-07-08 | Thermosetting resin composition from poly-arylene-oxy-bis-maleimide and polyarylene diamine |
| EP87306106A EP0253586B1 (en) | 1986-07-15 | 1987-07-10 | Thermosetting resin composition |
| DE3751839T DE3751839T2 (en) | 1986-07-15 | 1987-07-10 | Curable resin composition |
| EP91203079A EP0480543B1 (en) | 1986-07-15 | 1987-07-10 | Thermosetting resin composition |
| AU75523/87A AU589020B2 (en) | 1986-07-15 | 1987-07-10 | Thermosetting resins derived from bismaleimides and diamines |
| DE8787306106T DE3781843T2 (en) | 1986-07-15 | 1987-07-10 | COMPOSITION FOR HEAT-RESISTABLE RESIN. |
| KR1019870007622A KR910004043B1 (en) | 1986-07-15 | 1987-07-15 | Thermosetting resin composition |
| US07/304,558 US4960852A (en) | 1986-07-15 | 1989-02-01 | Thermosetting resin compostion from bis, maleimide and bis (meta-amino phenoxy) compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61190563A JPH0749484B2 (en) | 1986-08-15 | 1986-08-15 | Thermosetting resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6348334A JPS6348334A (en) | 1988-03-01 |
| JPH0749484B2 true JPH0749484B2 (en) | 1995-05-31 |
Family
ID=16260146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61190563A Expired - Fee Related JPH0749484B2 (en) | 1986-07-15 | 1986-08-15 | Thermosetting resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0749484B2 (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5945322A (en) * | 1982-09-08 | 1984-03-14 | Hitachi Chem Co Ltd | Preparation of polyaminobisimide resin |
| JP2533841B2 (en) * | 1984-12-18 | 1996-09-11 | 三井東圧化学株式会社 | Heat resistant adhesive |
-
1986
- 1986-08-15 JP JP61190563A patent/JPH0749484B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6348334A (en) | 1988-03-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |