JPH06345898A - Resin composition for molding material and molding by curing the same - Google Patents
Resin composition for molding material and molding by curing the sameInfo
- Publication number
- JPH06345898A JPH06345898A JP16326193A JP16326193A JPH06345898A JP H06345898 A JPH06345898 A JP H06345898A JP 16326193 A JP16326193 A JP 16326193A JP 16326193 A JP16326193 A JP 16326193A JP H06345898 A JPH06345898 A JP H06345898A
- Authority
- JP
- Japan
- Prior art keywords
- resin composition
- curing
- molding
- polyfunctional
- molding material
- 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
Links
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は成形材料用樹脂組成物及
びこれを硬化させて得られる成形品に関し、特に従来一
般に用いられているフェノール樹脂成形材料を強度、可
撓性、難燃性、電気特性等において総合的に凌駕するジ
ヒドロベンゾオキサジン系の成形材料用樹脂組成物及び
これを硬化させて得られる成形品に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a resin composition for a molding material and a molded product obtained by curing the resin composition. TECHNICAL FIELD The present invention relates to a dihydrobenzoxazine-based resin composition for molding material, which is superior in electrical properties and the like, and a molded product obtained by curing the same.
【０００２】[0002]
【従来の技術】熱硬化性樹脂を用いる成形材料には、従
来そのバランスのとれた機械特性、耐熱性、難燃性、電
気特性及び低価格なことからフェノール樹脂、メラミン
樹脂、ユリア樹脂等が用いられてきた。しかしこれらの
樹脂は、可撓性に劣ることに加え、電気部品の腐食の原
因となるアンモニアを発する（ヘキサメチレンテトラミ
ン硬化型ノボラック樹脂）、硬化時に縮合反応を伴うこ
とによりホルムアルデヒドや水を放出しボイドを生じる
（レゾール樹脂、メラミン樹脂）といった固有の欠点を
有し、更にこれらの揮発分は成形品表面及び金型を汚染
するという問題を生じる。2. Description of the Related Art As molding materials using thermosetting resins, phenol resins, melamine resins, urea resins, etc. have been used because of their well-balanced mechanical properties, heat resistance, flame retardancy, electrical properties and low price. Has been used. However, in addition to being inferior in flexibility, these resins emit ammonia that causes corrosion of electrical parts (hexamethylenetetramine curable novolac resin), and release formaldehyde and water due to a condensation reaction during curing. It has inherent defects such as generation of voids (resole resin, melamine resin), and further, these volatile components cause a problem of contaminating the surface of the molded article and the mold.
【０００３】上記の問題を解決するために不飽和ポリエ
ステル樹脂、エポキシ樹脂、ビスマレイミド樹脂が用い
られるが、これらは硬化時に揮発分を発することはない
ものの難燃性が不十分であることや価格が非常に高価で
ある場合が多く、実用レベルでフェノール樹脂を代替す
ることはできない。Unsaturated polyester resins, epoxy resins, and bismaleimide resins are used to solve the above problems, but they do not emit volatile components during curing, but their flame retardance is insufficient and their price is low. Are often very expensive, and cannot replace phenolic resins on a practical level.
【０００４】[0004]
【発明が解決しようとする課題】本発明は従来のフェノ
ール樹脂、メラミン樹脂等の成形材料では達成し得ない
良好な機械特性、電気特性、難燃性をバランスよく有す
る硬化時に揮発分を発しない成形材料用樹脂組成物とこ
れを硬化させて得られる成形品を提供することを目的と
する。The present invention has a good balance of good mechanical properties, electrical properties, and flame retardancy that cannot be achieved by conventional molding materials such as phenol resin and melamine resin, and does not emit volatile components during curing. It is an object to provide a resin composition for a molding material and a molded product obtained by curing the resin composition.
【０００５】[0005]
【課題を解決するための手段】かかる課題を解決するた
めに鋭意検討した結果、本発明者らは以下の新規な成形
材料用樹脂組成物及びこれを硬化して得られる成形品を
発明するに至った。即ち、本発明は（Ａ）式（Ｉ）に示
す多官能ジヒドロベンゾオキサジン化合物１０〜６０重
量％、（Ｂ）ガラス繊維又は有機繊維５〜７０重量％並
びに（Ｃ）無機質充填剤、硬化促進剤、離型剤、接着性
付与剤及び着色剤から選ばれる少なくとも１種からなる
添加剤０．５〜８０重量％からなる成形材料用樹脂組成
物を提供するものである。Means for Solving the Problems As a result of intensive investigations for solving the above problems, the inventors of the present invention have invented the following novel resin composition for a molding material and a molded product obtained by curing the resin composition. I arrived. That is, the present invention comprises (A) 10 to 60% by weight of the polyfunctional dihydrobenzoxazine compound represented by the formula (I), (B) 5 to 70% by weight of glass fiber or organic fiber, and (C) an inorganic filler and a curing accelerator. The present invention provides a resin composition for a molding material, which comprises 0.5 to 80% by weight of an additive comprising at least one selected from a release agent, an adhesiveness-imparting agent and a colorant.
【０００６】[0006]
【化３】 （式中、ｎは１〜４の整数であり、Ｒ1はフェニル基、
置換フェニル基、メチル基又はシクロヘキシル基であ
り、Ｒ2は[Chemical 3] (In the formula, n is an integer of 1 to 4, R 1 is a phenyl group,
A substituted phenyl group, a methyl group or a cyclohexyl group, and R 2 is
【０００７】[0007]
【化４】 であり、ただしｍは１以上の整数である。）本発明はま
た、上記成形材料用樹脂組成物を硬化させて得られる成
形品を提供するものである。[Chemical 4] Where m is an integer of 1 or more. ) The present invention also provides a molded product obtained by curing the resin composition for a molding material.
【０００８】式（Ｉ）に示した多官能ジヒドロベンゾオ
キサジン化合物は、対応する多官能フェノール、アミン
及びホルムアルデヒドから下記反応式（ＩＩ）に従って
合成することができる。また米国特許第５１５２９３９
号明細書に示されるように、これら多官能ジヒドロベン
ゾオキサジン化合物は適当な加熱により開環重合反応を
起こし、揮発分を全く発することなく優れた特性を持つ
架橋構造を形成する。The polyfunctional dihydrobenzoxazine compound represented by the formula (I) can be synthesized from the corresponding polyfunctional phenol, amine and formaldehyde according to the following reaction formula (II). See also US Pat. No. 5,152,939.
As shown in the specification, these polyfunctional dihydrobenzoxazine compounds cause a ring-opening polymerization reaction by appropriate heating and form a crosslinked structure having excellent properties without generating any volatile matter.
【０００９】[0009]
【化５】 （式中、Ｒ1、Ｒ2及びｎは先に記載したと同じ意味を有
する。）なお、Ｒ1の１種である置換フェニル基の例と
しては、メチルフェニル基及びビニルフェニル基が挙げ
られる。[Chemical 5] (In the formula, R 1 , R 2 and n have the same meaning as described above.) Examples of the substituted phenyl group which is one kind of R 1 include a methylphenyl group and a vinylphenyl group. .
【００１０】この多官能ジヒドロベンゾオキサジン化合
物として具体的には、例えば、Specific examples of the polyfunctional dihydrobenzoxazine compound include, for example,
【００１１】[0011]
【化６】 [Chemical 6]
【００１２】[0012]
【化７】 [Chemical 7]
【００１３】[0013]
【化８】 等が使用でき、これらのうち２種類以上を組み合わせて
用いることもできる。またこれらの多官能ジヒドロベン
ゾオキサジン化合物を予め８０〜１８０℃、好ましくは
１２０〜１６０℃で３０〜３００分間熱処理することに
より、その一部を予備重合させ成形時の硬化速度や溶融
粘度を調節することもできる。[Chemical 8] Etc. can be used, and it is also possible to use two or more of them in combination. Further, these polyfunctional dihydrobenzoxazine compounds are preliminarily heat-treated at 80 to 180 ° C., preferably 120 to 160 ° C. for 30 to 300 minutes to preliminarily partly polymerize them and adjust the curing speed and melt viscosity during molding. You can also
【００１４】また、本発明において用いられるガラス繊
維は、樹脂の補強効果と成形時の金型磨耗の観点から繊
維径５〜２０μｍのものが好ましい。ガラス繊維の好ま
しい配合割合は５〜６０重量％である。Further, the glass fiber used in the present invention preferably has a fiber diameter of 5 to 20 μm from the viewpoint of the reinforcing effect of the resin and the wear of the mold during molding. The preferable blending ratio of the glass fiber is 5 to 60% by weight.
【００１５】本発明において用いられる有機繊維として
は、樹脂の補強効果と成形品の耐熱性の観点から綿フロ
ック、綿織布、α−セルロース、パルプ、木粉のうちか
ら選ばれる１種又は２種以上の混合物が好適に用いられ
る。As the organic fiber used in the present invention, one or two selected from cotton flock, cotton woven fabric, α-cellulose, pulp and wood flour from the viewpoint of the reinforcing effect of the resin and the heat resistance of the molded product. Mixtures of one or more are preferably used.
【００１６】本発明の樹脂組成物は上記の多官能ジヒド
ロベンゾオキサジン化合物及びガラス繊維若しくは有機
繊維以外に、無機質充填剤、硬化促進剤、離型材、接着
性付与剤及び着色剤から選ばれる少なくとも１種からな
る添加剤を含有する。これらの添加剤は、耐熱性、機械
特性の増大、多官能ジヒドロベンゾオキサジン化合物の
硬化速度の増大、成形時の硬化物の金型からの離型、樹
脂（多官能ジヒドロベンゾオキサジン化合物）／充填材
間の界面接着強度の増大等を目的として配合される。The resin composition of the present invention comprises, in addition to the above-mentioned polyfunctional dihydrobenzoxazine compound and glass fiber or organic fiber, at least one selected from inorganic fillers, curing accelerators, mold release agents, adhesiveness imparting agents and colorants. Contains an additive consisting of seeds. These additives are heat resistance, increase in mechanical properties, increase in curing rate of polyfunctional dihydrobenzoxazine compound, release of cured product from mold during molding, resin (polyfunctional dihydrobenzoxazine compound) / filling It is mixed for the purpose of increasing the interfacial adhesion strength between materials.
【００１７】無機質充填剤としては、クレー、マイカ、
タルク、ゼオライト等が用いられる。好ましい配合割合
は５〜３０重量％である。硬化促進剤としては、例え
ば、カテコール、ビスフェノールＡ等の多官能フェノー
ル類やｐ−トルエンスルホン酸、ｐ−フェノールスルホ
ン酸等のスルホン酸類のうち１種又は２種以上の混合物
が、離型剤としては、例えば、ステアリン酸亜鉛などの
ステアリン酸塩やカルナバワックス等が、接着性付与剤
としては、例えば、シラン系カップリング剤が、着色剤
としては、例えば、カーボンブラック等を用いることが
できる。また、必要に応じて更に難燃性向上剤としてほ
う酸や水酸化アルミニウム等を添加剤として用いること
もできる。As the inorganic filler, clay, mica,
Talc, zeolite, etc. are used. A preferred blending ratio is 5 to 30% by weight. As the curing accelerator, for example, one or a mixture of two or more of polyfunctional phenols such as catechol and bisphenol A and sulfonic acids such as p-toluenesulfonic acid and p-phenolsulfonic acid is used as a release agent. Examples thereof include stearates such as zinc stearate and carnauba wax, examples of the adhesiveness-imparting agent include silane coupling agents, and examples of the coloring agent include carbon black. Further, if necessary, boric acid, aluminum hydroxide or the like can be used as an additive as a flame retardant improver.
【００１８】本発明の成形材料用樹脂組成物の各成分の
配合比は、組成物の強度、耐熱性、成形時の溶融粘度や
金型磨耗性の観点から、多官能ジヒドロベンゾオキサジ
ン化合物１０〜６０重量％、ガラス繊維又は有機繊維５
〜７０重量％及び添加剤０．５〜８０重量％である。The blending ratio of each component of the resin composition for molding materials of the present invention is such that the polyfunctional dihydrobenzoxazine compound 10 to 10 is used in view of the strength of the composition, heat resistance, melt viscosity at the time of molding, and mold abrasion resistance. 60% by weight, glass fiber or organic fiber 5
˜70% by weight and 0.5 to 80% by weight of additives.
【００１９】また、本発明は上記成形材料用樹脂組成物
を硬化して得られる成形品も提供するものである。上記
の成形品の製造方法は特に限定はされないが、通常、３
成分を加熱ロール等により６０〜１２０℃で混練して成
形材料用樹脂組成物を調製し、次いで得られた成形材料
用樹脂組成物を１８０〜２２０℃、成形圧２０〜７０ｋ
ｇｆ／ｃｍ2で３〜１０分間圧縮成形又は移送成形する
ことによって得られる。成形後、更に、１８０〜２２０
℃で５〜１２０分間後硬化させることにより、より良好
な特性を有する成形品が得られる。The present invention also provides a molded product obtained by curing the above resin composition for a molding material. The method for producing the above-mentioned molded article is not particularly limited, but usually 3
The components are kneaded at 60 to 120 ° C. with a heating roll or the like to prepare a resin composition for molding material, and then the obtained resin composition for molding material is 180 to 220 ° C., molding pressure is 20 to 70 k.
It is obtained by compression molding or transfer molding at gf / cm 2 for 3 to 10 minutes. After molding, 180-220
By post-curing at 5 ° C. for 5 to 120 minutes, a molded product having better properties can be obtained.
【００２０】[0020]
【実施例】以下、本発明の実施例及びその比較例によっ
て本発明を更に具体的に説明するが、本発明はこれらの
実施例に限定されるものではない。The present invention will be described in more detail below with reference to examples of the present invention and comparative examples thereof, but the present invention is not limited to these examples.
【００２１】実施例１〜１４、比較例１〜６ 表１及び表３に示す配合組成により原材料を混合し、二
軸加熱ロールを用いて８０℃で５分間混練後、混練物を
粉砕し、粉末状の樹脂組成物を作製した。実施例１〜１
４においては２００℃、５０ｋｇｆ／ｃｍ2、８分間、
また比較例１〜６においては１６０℃、１００ｋｇｆ／
ｃｍ2、３分間の条件で各樹脂組成物の移送成形を行
い、各成形品を作製した。なお、実施例１〜１４におい
ては後硬化を２００℃で３０分間行った。Examples 1 to 14 and Comparative Examples 1 to 6 Raw materials were mixed according to the compounding compositions shown in Tables 1 and 3 and kneaded at 80 ° C. for 5 minutes using a biaxial heating roll, and then the kneaded material was crushed, A powdery resin composition was prepared. Examples 1 to 1
No. 4, 200 ° C., 50 kgf / cm 2 , 8 minutes,
In Comparative Examples 1 to 6, 160 ° C. and 100 kgf /
Transfer molding of each resin composition was carried out under the condition of cm 2 for 3 minutes to produce each molded product. In addition, in Examples 1 to 14, post-curing was performed at 200 ° C. for 30 minutes.
【００２２】また、各成形品の特性は、機械特性、電気
特性についてはＪＩＳ−Ｋ６９１１に準じ、難燃性につ
いてはＵＬ−９４に準じて測定した。また、成形品外観
及び金型汚れについては名機製作所製Ｍ−１００Ａ−Ｔ
Ｓ型射出成形機を用い、成形材料５０ｋｇを上記と同様
に成形して目視により評価した。これらの評価結果を表
２及び表４に示す。The characteristics of each molded product were measured according to JIS-K6911 for mechanical characteristics and electrical characteristics, and according to UL-94 for flame retardancy. Also, regarding the appearance of the molded product and stains on the mold, M-100A-T manufactured by Meiki Seisakusho
Using an S-type injection molding machine, 50 kg of molding material was molded in the same manner as above and evaluated visually. The evaluation results are shown in Tables 2 and 4.
【００２３】[0023]
【表１】 [Table 1]
【００２４】[0024]
【化９】 [Chemical 9]
【００２５】[0025]
【表２】 [Table 2]
【００２６】[0026]
【表３】 [Table 3]
【００２７】[0027]
【表４】 [Table 4]
【００２８】[0028]
【発明の効果】本発明により、従来のフェノール樹脂、
メラミン樹脂等の成形材料では達成し得ない良好な機械
特性、電気特性、燃焼性をバランスよく有する成形材料
用樹脂組成物が得られた。また、硬化時に揮発分を発し
ないため金型汚れが少なく外観の良好な成形品が得られ
た。According to the present invention, a conventional phenol resin,
A resin composition for a molding material having a good balance of mechanical properties, electrical characteristics and flammability, which cannot be achieved by a molding material such as a melamine resin, was obtained. In addition, since a volatile matter was not generated during curing, a molded product with a small appearance and a good appearance was obtained.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 佐藤 愛彦 茨城県結城市大字鹿窪1772−１ 日立化成 工業株式会社南結城工場内 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Aihiko Sato, 172-1 Kagoku, Yuki-shi, Ibaraki Hitachi Chemical Co., Ltd. Minami-Yuki Plant
Claims (2)
ンゾオキサジン化合物１０〜６０重量％、（Ｂ）ガラス
繊維又は有機繊維５〜７０重量％並びに（Ｃ）無機質充
填剤、硬化促進剤、離型剤、接着性付与剤及び着色剤か
ら選ばれる少なくとも１種からなる添加剤０．５〜８０
重量％からなる成形材料用樹脂組成物。 【化１】 （式中、ｎは１〜４の整数であり、Ｒ1はフェニル基、
置換フェニル基、メチル基又はシクロヘキシル基であ
り、Ｒ2は 【化２】 であり、ただしｍは１以上の整数である。）1. A polyfunctional dihydrobenzoxazine compound represented by the formula (I) (10 to 60% by weight), glass fiber or organic fiber (B) 5 to 70% by weight, and (C) an inorganic filler and a curing accelerator. 0.5-80, at least one additive selected from the group consisting of a release agent, a release agent, an adhesiveness-imparting agent and a coloring agent.
A resin composition for molding material, which is composed by weight. [Chemical 1] (In the formula, n is an integer of 1 to 4, R 1 is a phenyl group,
A substituted phenyl group, a methyl group or a cyclohexyl group, and R 2 is Where m is an integer of 1 or more. )
硬化させて得られる成形品。2. A molded article obtained by curing the resin composition for a molding material according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16326193A JPH06345898A (en) | 1993-06-08 | 1993-06-08 | Resin composition for molding material and molding by curing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16326193A JPH06345898A (en) | 1993-06-08 | 1993-06-08 | Resin composition for molding material and molding by curing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06345898A true JPH06345898A (en) | 1994-12-20 |
Family
ID=15770448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16326193A Pending JPH06345898A (en) | 1993-06-08 | 1993-06-08 | Resin composition for molding material and molding by curing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06345898A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09272786A (en) * | 1996-02-09 | 1997-10-21 | Hitachi Chem Co Ltd | Thermosetting resin composition and its cured item |
| JPH09283876A (en) * | 1996-04-12 | 1997-10-31 | Hitachi Chem Co Ltd | Laminated board for printed wiring board |
| WO2003042196A1 (en) * | 2001-11-13 | 2003-05-22 | Henkel Corporation | Benzoxazineshaving polymerizable side groups, thermosetting resi ns comprised thereof, and methods for use thereof |
| WO2005000955A1 (en) * | 2003-06-27 | 2005-01-06 | Henkel Corporation | Heat curable compositions comprising a benzoxazine component and an acrylonitrile-butadiene copolymer having secondary amine terminal groups as a toughener |
| JP2009173807A (en) * | 2008-01-25 | 2009-08-06 | Akebono Brake Ind Co Ltd | Binder resin composition for friction material, thermosetting resin composite material containing the same and friction material |
| US7649060B2 (en) | 2005-12-02 | 2010-01-19 | Henkel Corporation | Curable compositions |
| US7666938B2 (en) | 2004-12-03 | 2010-02-23 | Henkel Corporation | Nanoparticle silica filled benzoxazine compositions |
| US7709579B2 (en) | 2003-08-18 | 2010-05-04 | Henkel Corporation | Curable compositions for advanced processes, and products made therefrom |
| US8029889B1 (en) | 2004-12-03 | 2011-10-04 | Henkel Corporation | Prepregs, towpregs and preforms |
| JP2019108516A (en) * | 2017-12-15 | 2019-07-04 | 住友ベークライト株式会社 | Thermosetting resin composition, and cured product thereof, prepreg, laminate, metal base substrate and power module |
| CN117247654A (en) * | 2023-11-17 | 2023-12-19 | 西南石油大学 | Water-soluble benzoxazine and inorganic fiber composite aerogel and preparation method thereof |
-
1993
- 1993-06-08 JP JP16326193A patent/JPH06345898A/en active Pending
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09272786A (en) * | 1996-02-09 | 1997-10-21 | Hitachi Chem Co Ltd | Thermosetting resin composition and its cured item |
| JPH09283876A (en) * | 1996-04-12 | 1997-10-31 | Hitachi Chem Co Ltd | Laminated board for printed wiring board |
| WO2003042196A1 (en) * | 2001-11-13 | 2003-05-22 | Henkel Corporation | Benzoxazineshaving polymerizable side groups, thermosetting resi ns comprised thereof, and methods for use thereof |
| US7649037B1 (en) | 2003-06-27 | 2010-01-19 | Henkel Corporation | Curable compositions |
| US7157509B2 (en) | 2003-06-27 | 2007-01-02 | Henkel Corporation | Curable compositions |
| JP2007524728A (en) * | 2003-06-27 | 2007-08-30 | ヘンケル コーポレイション | Thermosetting composition comprising a benzoxazine component and an acrylonitrile-butadiene copolymer having secondary amine end groups as reinforcing agents |
| KR101138121B1 (en) * | 2003-06-27 | 2012-04-23 | 헨켈 코포레이션 | Heat curable compositions comprising a benzoxazine component and an acrylonitrile-butadiene copolymer having secondary amine terminal groups as a toughener |
| JP4707662B2 (en) * | 2003-06-27 | 2011-06-22 | ヘンケル コーポレイション | Thermosetting composition comprising a benzoxazine component and an acrylonitrile-butadiene copolymer having secondary amine end groups as reinforcing agents |
| WO2005000955A1 (en) * | 2003-06-27 | 2005-01-06 | Henkel Corporation | Heat curable compositions comprising a benzoxazine component and an acrylonitrile-butadiene copolymer having secondary amine terminal groups as a toughener |
| US7709579B2 (en) | 2003-08-18 | 2010-05-04 | Henkel Corporation | Curable compositions for advanced processes, and products made therefrom |
| US7666938B2 (en) | 2004-12-03 | 2010-02-23 | Henkel Corporation | Nanoparticle silica filled benzoxazine compositions |
| US8029889B1 (en) | 2004-12-03 | 2011-10-04 | Henkel Corporation | Prepregs, towpregs and preforms |
| US7649060B2 (en) | 2005-12-02 | 2010-01-19 | Henkel Corporation | Curable compositions |
| JP2009173807A (en) * | 2008-01-25 | 2009-08-06 | Akebono Brake Ind Co Ltd | Binder resin composition for friction material, thermosetting resin composite material containing the same and friction material |
| JP2019108516A (en) * | 2017-12-15 | 2019-07-04 | 住友ベークライト株式会社 | Thermosetting resin composition, and cured product thereof, prepreg, laminate, metal base substrate and power module |
| CN117247654A (en) * | 2023-11-17 | 2023-12-19 | 西南石油大学 | Water-soluble benzoxazine and inorganic fiber composite aerogel and preparation method thereof |
| CN117247654B (en) * | 2023-11-17 | 2024-02-09 | 西南石油大学 | Water-soluble benzoxazine and inorganic fiber composite aerogel and preparation method thereof |
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