JPH05339342A - Thermosetting resin composition - Google Patents
Thermosetting resin compositionInfo
- Publication number
- JPH05339342A JPH05339342A JP15364192A JP15364192A JPH05339342A JP H05339342 A JPH05339342 A JP H05339342A JP 15364192 A JP15364192 A JP 15364192A JP 15364192 A JP15364192 A JP 15364192A JP H05339342 A JPH05339342 A JP H05339342A
- Authority
- JP
- Japan
- Prior art keywords
- resin
- modified
- phenol
- polyphenylene ether
- 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.)
- Granted
Links
Classifications
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Epoxy Resins (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、作業性が良好で、耐熱
性と靭性、更には難燃性、接着性に優れた低誘電率積層
板用に特に有用な熱硬化性樹脂組成物に関するものであ
る。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a thermosetting resin composition which is particularly useful for a low dielectric constant laminate having excellent workability, heat resistance and toughness, flame retardancy and adhesiveness. It is a thing.
【０００２】[0002]
【従来の技術】近年、高周波領域で用いられるプリント
配線板に、耐熱性で、低誘電率、低誘電正接の積層板用
樹脂が望まれている。これに対し、誘電率の小さいフッ
素樹脂やポリフェニレンエーテルなどの熱可塑性樹脂が
提案されているが、作業性、接着性が悪く、信頼性に欠
けるなどの問題点がある。そこで、作業性、接着性を改
善する目的で、エポキシ変性ポリフェニレンエーテル樹
脂、あるいはポリフェニレンエーテル変性エポキシ樹脂
も提案されているが、エポキシ樹脂の誘電率が高く、耐
熱性が低いため、満足な特性が得られていない。また、
エポキシ樹脂よりは誘電率が低く、耐熱性の良好な樹脂
として、シアネートエステル樹脂が公知であるが、硬化
樹脂は脆く、誘電率がまだ不充分であり、難燃性にも劣
っていた。2. Description of the Related Art In recent years, heat-resistant, low dielectric constant, low dielectric loss tangent resin for laminates has been desired for printed wiring boards used in a high frequency range. On the other hand, a thermoplastic resin such as a fluororesin or polyphenylene ether having a small dielectric constant has been proposed, but it has problems such as poor workability and adhesiveness and lack of reliability. Therefore, in order to improve workability and adhesiveness, an epoxy-modified polyphenylene ether resin or a polyphenylene ether-modified epoxy resin has also been proposed, but since the epoxy resin has a high dielectric constant and low heat resistance, satisfactory properties are obtained. Not obtained. Also,
Cyanate ester resin is known as a resin having a lower dielectric constant and better heat resistance than an epoxy resin, but a cured resin is brittle, its dielectric constant is still insufficient, and its flame retardancy is poor.
【０００３】[0003]
【発明が解決しようとする課題】本発明の目的とすると
ころは、作業性が良好で、耐熱性、靭性、更には難燃
性、接着性に優れた低誘電率積層板用熱硬化性樹脂組成
物を提供するにある。The object of the present invention is to provide a thermosetting resin for low dielectric constant laminates which has good workability, heat resistance, toughness, flame retardancy and adhesiveness. Providing a composition.
【０００４】[0004]
【課題を解決するための手段】本発明は、式（１）で示
されるジシアネートエステル化合物とフェノール変性石
油樹脂、フェノール変性石炭樹脂及びフェノール変性ポ
リブタジエン樹脂からなる群より選ばれる１種又は２種
以上の変性樹脂とを反応させてなる変性シアネート樹脂
（Ａ）と、ポリフェニレンエーテル（Ｂ）と、臭素化エ
ポキシ樹脂（Ｃ）とを含有する熱硬化性樹脂組成物であ
る。The present invention is one or two selected from the group consisting of a dicyanate ester compound represented by the formula (1), a phenol-modified petroleum resin, a phenol-modified coal resin and a phenol-modified polybutadiene resin. A thermosetting resin composition containing a modified cyanate resin (A) obtained by reacting the above modified resin, a polyphenylene ether (B), and a brominated epoxy resin (C).
【０００５】[0005]
【化１】 [Chemical 1]
【０００６】[0006]
【作用】本発明において用いられるジシアネートエステ
ル化合物は、式（１）で示されるものである。式（１）
の好ましいジシアネートエステル化合物の例として、ビ
ス(4-シアネートフェニル)メタン、ビス(3-メチル-4-シ
アネートフェニル)メタン、ビス(3-エチル-4-シアネー
トフェニル)メタン、ビス(3,5-ジメチル-4-シアネート
フェニル)メタン、1,1-ビス(4-シアネートフェニル)エ
タン、2,2-ビス(4-シアネートフェニル)プロパン、2,2-ビス(4-シ
アネートフェニル)-1,1,1,3,3,3-ヘキサフルオロプロパ
ン、ジ(4-シアネートフェニル)エーテル、ジ(4-シアネ
ートフェニル)チオエーテル、4,4-ジシアネート-ジフェ
ニルなどが挙げられる。The dicyanate ester compound used in the present invention is represented by the formula (1). Formula (1)
Examples of preferred dicyanate ester compounds of bis (4-cyanatephenyl) methane, bis (3-methyl-4-cyanatephenyl) methane, bis (3-ethyl-4-cyanatephenyl) methane, bis (3,5 -Dimethyl-4-cyanatephenyl) methane, 1,1-bis (4-cyanatephenyl) ethane, 2,2-bis (4-cyanatephenyl) propane, 2,2-bis (4-cyanatephenyl) -1, 1,1,3,3,3-hexafluoropropane, di (4-cyanatephenyl) ether, di (4-cyanatephenyl) thioether, 4,4-dicyanate-diphenyl and the like can be mentioned.
【０００７】本発明で用いられるフェノール変性石油樹
脂は、石油の分解油留分に含まれるジオレフィン及びモ
ノオレフィン類をフェノール類と共重合させたものであ
る。更に詳しくは、分解油留分のうち、Ｃ5留分を原料
にしたＣ5系（脂肪族系）石油樹脂、Ｃ9留分を原料にし
たＣ9系（芳香族系）石油樹脂、Ｃ5Ｃ9共重合石油樹
脂、又はＣ5留分に含まれるシクロペンタジエンを熱二
量化して得られるジシクロペンタジエンを原料にしたジ
シクロペンタジエン樹脂などに、フェノール類を付加さ
せた石油樹脂である。これらの中で特に芳香族系のＣ9
系石油樹脂又はＣ5Ｃ9共重合石油樹脂は、シアネートエ
ステル樹脂とポリフェニレンエーテルとの相溶性を良く
し、作業性、接着性、靭性の向上に著しく有効である。The phenol-modified petroleum resin used in the present invention is obtained by copolymerizing diolefins and monoolefins contained in a cracked oil fraction of petroleum with phenols. More specifically, among the cracked oil fraction, C 5 system in which the C 5 fraction in material (aliphatic) petroleum resins, C 9 system in which a C 9 fraction to the raw material (aromatic) petroleum resin, C A petroleum resin obtained by adding phenols to a 5 C 9 copolymerized petroleum resin or a dicyclopentadiene resin obtained by dimerizing cyclopentadiene contained in a C 5 fraction by thermal dimerization. .. Among these, particularly aromatic C 9
The petroleum resin or the C 5 C 9 copolymer petroleum resin improves the compatibility between the cyanate ester resin and the polyphenylene ether, and is extremely effective in improving workability, adhesiveness and toughness.
【０００８】本発明で用いられるフェノール変性石炭樹
脂は、石炭の分解油留分に含まれるスチレン、ビニルト
ルエン、クマロン、インデンなどをフェノール類と付加
重合させたものであり、シアネートエステル樹脂とポリ
フェニレンエーテルとの相溶性を良くし、作業性、接着
性、靭性の向上に著しく有効である。The phenol-modified coal resin used in the present invention is obtained by addition-polymerizing styrene, vinyltoluene, coumarone, indene and the like contained in the cracked oil fraction of coal with phenols, and a cyanate ester resin and polyphenylene ether. It is highly effective in improving workability, adhesiveness and toughness.
【０００９】本発明で用いられるフェノール変性ポリブ
タジエン樹脂は、分子量300〜2000のポリブタジエンを
フェノール類と付加重合させたものである。ポリブタジ
エンの分子量が300より低いと良好な靭性が得られず、2
000より高いと耐熱性が低下する。フェノール変性ポリ
ブタジエン樹脂は、シアネートエステル樹脂とポリフェ
ニレンエーテルとの相溶性を良くし、作業性、接着性、
靭性の向上に著しく有効である。The phenol-modified polybutadiene resin used in the present invention is obtained by addition-polymerizing polybutadiene having a molecular weight of 300 to 2000 with phenols. If the molecular weight of polybutadiene is lower than 300, good toughness cannot be obtained.
If it is higher than 000, the heat resistance will decrease. Phenol-modified polybutadiene resin improves the compatibility of cyanate ester resin and polyphenylene ether, and improves workability, adhesiveness,
Remarkably effective in improving toughness.
【００１０】フェノール類としては、フェノール、クレ
ゾール、キシレノールなどが使用される。フェノール類
の含有量は、フェノール変性石油樹脂中の5重量％以
上、50重量％以下で、かつ分子当り平均1〜3個付加した
ものが好ましい。フェノール類の含有量が5重量％未満
では、Ｔｇが低く、良好な靭性が得られない。また50重
量％を越えると、積層板の誘電率、吸水率が大きくな
る。As the phenols, phenol, cresol, xylenol and the like are used. The content of phenols is preferably 5% by weight or more and 50% by weight or less in the phenol-modified petroleum resin, and an average of 1 to 3 added per molecule is preferable. When the content of phenols is less than 5% by weight, Tg is low and good toughness cannot be obtained. On the other hand, when it exceeds 50% by weight, the dielectric constant and water absorption of the laminated plate increase.
【００１１】フェノール変性石油樹脂、フェノール変性
石炭樹脂又はフェノール変性ポリブタジエン樹脂は、ジ
シアネートエステル化合物100重量部に対し、5重量部以
上50重量部以下が好ましい。5重量部未満では、硬化性
が悪く、積層板の誘電率、吸水率も大きくなる。また50
重量部を越えると、耐熱性が低下し、良好な靭性が得ら
れない。The amount of the phenol-modified petroleum resin, phenol-modified coal resin or phenol-modified polybutadiene resin is preferably 5 parts by weight or more and 50 parts by weight or less based on 100 parts by weight of the dicyanate ester compound. If it is less than 5 parts by weight, the curability will be poor and the dielectric constant and water absorption of the laminate will be large. Again 50
When it exceeds the weight part, the heat resistance is lowered and good toughness cannot be obtained.
【００１２】ジシアネートエステル化合物とフェノール
変性石油樹脂、フェノール変性石炭樹脂又はフェノール
変性ポリブタジエン樹脂は、100〜200℃に加熱して、融
点が50℃以上100℃以下になるよう、予め反応させて、
変性シアネートエステル樹脂とすることが望ましいが、
場合によっては反応させないで（Ｂ）、（Ｃ）成分と混
合して用いることも可能である。The dicyanate ester compound and the phenol-modified petroleum resin, phenol-modified coal resin or phenol-modified polybutadiene resin are heated to 100 to 200 ° C. and pre-reacted so that the melting point is from 50 ° C. to 100 ° C.
It is desirable to use a modified cyanate ester resin,
In some cases, it may be used as a mixture with the components (B) and (C) without reaction.
【００１３】本発明で用いられるポリフェニレンエーテ
ルは、式（２）で示されるものである。The polyphenylene ether used in the present invention is represented by the formula (2).
【００１４】[0014]
【化２】 [Chemical 2]
【００１５】式（２）の好ましいポリフェニレンエーテ
ルの例として、ポリ(2,6-ジメチル-1,4-フェニレンエー
テル）が用いられる。その分子量は、特に限定されるも
のではないが、数平均分子量3000以上200000以下のもの
が好ましい。分子量が3000未満であると、耐熱性、靭性
が低下し、200000を越えると、相溶性、作業性が低下す
る。Poly (2,6-dimethyl-1,4-phenylene ether) is used as an example of the preferred polyphenylene ether of formula (2). The molecular weight is not particularly limited, but a number average molecular weight of 3,000 or more and 200,000 or less is preferable. When the molecular weight is less than 3000, heat resistance and toughness are deteriorated, and when it exceeds 200,000, compatibility and workability are deteriorated.
【００１６】ポリフェニレンエーテルは、変性シアネー
トエステル樹脂100重量部に対し、5重量部以上50重量部
以下が好ましい。5重量部未満では、靭性が向上せず、
ドリル加工時にクラックが発生しやすくなる。50重量部
を越えると、ワニスとした時の粘度が極度に増大し、作
業性、接着性が悪化する。The polyphenylene ether is preferably used in an amount of 5 parts by weight or more and 50 parts by weight or less with respect to 100 parts by weight of the modified cyanate ester resin. If it is less than 5 parts by weight, the toughness does not improve,
Cracks are likely to occur during drilling. If the amount exceeds 50 parts by weight, the viscosity of the varnish is extremely increased and the workability and the adhesiveness are deteriorated.
【００１７】臭素化エポキシ樹脂は、変性シアネートエ
ステル樹脂にポリフェニリンエーテルを配合した熱硬化
性樹脂組成物100重量部に対して10〜50重量部が好まし
い。臭素化エポキシ樹脂を適当量配合することにより、
耐熱性の低下などの副作用を起こさず、接着性が向上
し、難燃性を有する低εの積層板を得ることができる。
10重量部未満では難燃性が得られず、50重量部を越える
と誘電率が上昇してしまう。臭素化エポキシ樹脂は、ジ
シアネートエステル化合物と変性樹脂とを予め反応させ
たものに予備反応させておいて用いることもできる。The brominated epoxy resin is preferably used in an amount of 10 to 50 parts by weight based on 100 parts by weight of the thermosetting resin composition prepared by blending the modified cyanate ester resin with polyphenylene ether. By blending an appropriate amount of brominated epoxy resin,
It is possible to obtain a laminate having a low ε and having improved flame retardancy and adhesiveness without causing side effects such as reduction in heat resistance.
If it is less than 10 parts by weight, flame retardancy cannot be obtained, and if it exceeds 50 parts by weight, the dielectric constant increases. The brominated epoxy resin can also be used by preliminarily reacting a dicyanate ester compound with a modified resin.
【００１８】ワニス溶剤としては、特に限定されるもの
ではないが、例えば、ベンゼン、トルエン、キシレンな
どの芳香族炭化水素類が好ましい。The varnish solvent is not particularly limited, but for example, aromatic hydrocarbons such as benzene, toluene and xylene are preferable.
【００１９】本発明の組成物は、必要に応じて、ノニル
フェノール、ナフテン酸コバルト、ナフテン酸亜鉛など
の硬化促進剤を併用することもできる。In the composition of the present invention, a curing accelerator such as nonylphenol, cobalt naphthenate or zinc naphthenate may be used in combination, if necessary.
【００２０】[0020]
（実施例１〜３）撹拌装置、減圧蒸留装置及び温度計を
付けた反応容器に、ジシアネートエステル化合物とフェ
ノール変性石油樹脂、フェノール変性石炭樹脂又はフェ
ノール変性ポリブタジエン樹脂と、ナフテン酸コバルト
を表１の処方に従って入れ、加熱する。減圧下（約20mm
Hg）、150℃で融点が70〜80℃になるよう反応させた。
生成樹脂の融点は表１に示した。(Examples 1 to 3) A reaction vessel equipped with a stirrer, a vacuum distillation apparatus and a thermometer was charged with a dicyanate ester compound, a phenol-modified petroleum resin, a phenol-modified coal resin or a phenol-modified polybutadiene resin, and cobalt naphthenate. Add according to the prescription and heat. Under reduced pressure (about 20 mm
Hg) at 150 ° C. and reacted at a melting point of 70-80 ° C.
The melting point of the produced resin is shown in Table 1.
【００２１】[0021]
【表１】 [Table 1]
【００２２】（実施例４〜６）変性シアネートエステル
樹脂を、表２に示す配合に従って、トルエンに溶解し
た。ワニスの外観は良好であった。このワニスを、表面
処理を行ったガラスクロスに含浸させ、乾燥機中で、13
0℃３分間加熱して溶剤を除去し、プリプレグを作成し
た。このプリプレグを８枚重ね、その両側に片面粗化銅
箔（35μm）を重ねて、180℃、２時間、加熱加圧して銅
張り積層板を得た。さらに180℃、８時間後硬化させた
ものの積層板特性を表２に示した。実施例４〜６の誘電
率、誘電正接は小さく、接着性、吸水率、ドリル加工
性、更には難燃性も良好であった。(Examples 4 to 6) The modified cyanate ester resin was dissolved in toluene according to the formulation shown in Table 2. The appearance of the varnish was good. This varnish was impregnated into a glass cloth that had been surface-treated and was dried in a dryer for 13
The solvent was removed by heating at 0 ° C. for 3 minutes to prepare a prepreg. Eight sheets of this prepreg were overlaid, a single-sided roughened copper foil (35 μm) was overlaid on both sides, and heated and pressed at 180 ° C. for 2 hours to obtain a copper-clad laminate. Table 2 shows the laminated plate properties of the product which was further cured at 180 ° C for 8 hours. The dielectric constant and dielectric loss tangent of Examples 4 to 6 were small, and the adhesiveness, water absorption, drill workability, and flame retardancy were also good.
【００２３】[0023]
【表２】 [Table 2]
【００２４】（比較例１〜３）実施例１〜３の変性シア
ネートエステル樹脂に、臭素化エポキシ樹脂を加えない
で表２の配合に従って実施例４〜６と同様に行った。誘
電率、誘電正接は小さく、吸水率、ドリル加工性は良好
であったが、難燃性は劣っていた。Comparative Examples 1 to 3 The modified cyanate ester resins of Examples 1 to 3 were prepared in the same manner as in Examples 4 to 6 according to the formulation shown in Table 2 without adding a brominated epoxy resin. The dielectric constant and dielectric loss tangent were small, and the water absorption rate and drill workability were good, but the flame retardancy was poor.
【００２５】[0025]
【発明の効果】本発明の熱硬化性樹脂組成物は作業性が
良好で、これを用いた積層板は高Ｔｇであり、吸水率が
小さく、靭性に優れ、ドリル加工時にクラックの発生も
なく、かつ誘電率、誘電正接の値も小さい。更に難燃
性、接着性にも優れている。低誘電率積層板、低誘電率
多層プリント板用熱硬化性樹脂として、非常に信頼性の
高い優れたものである。EFFECTS OF THE INVENTION The thermosetting resin composition of the present invention has good workability, a laminated plate using the same has a high Tg, a low water absorption rate, excellent toughness, and no cracking during drilling. Moreover, the values of the dielectric constant and the dielectric loss tangent are also small. It also has excellent flame retardancy and adhesiveness. It is a highly reliable and excellent thermosetting resin for low dielectric constant laminated boards and low dielectric constant multilayer printed boards.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｈ０１Ｌ 23/29 23/31 ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Office reference number FI technical display location H01L 23/29 23/31
Claims (1)
ル化合物とフェノール変性石油樹脂、フェノール変性石
炭樹脂及びフェノール変性ポリブタジエン樹脂からなる
群より選ばれる１種又は２種以上の変性樹脂とを反応さ
せてなる変性シアネート樹脂（Ａ）と、ポリフェニレン
エーテル（Ｂ）と、臭素化エポキシ樹脂（Ｃ）とを含有
することを特徴とする熱硬化性樹脂組成物。 【化１】 1. A reaction between a dicyanate ester compound represented by the formula (1) and one or more modified resins selected from the group consisting of phenol-modified petroleum resin, phenol-modified coal resin and phenol-modified polybutadiene resin. A thermosetting resin composition comprising a modified cyanate resin (A), a polyphenylene ether (B), and a brominated epoxy resin (C). [Chemical 1]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4153641A JP2524453B2 (en) | 1992-06-12 | 1992-06-12 | Thermosetting resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4153641A JP2524453B2 (en) | 1992-06-12 | 1992-06-12 | Thermosetting resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05339342A true JPH05339342A (en) | 1993-12-21 |
| JP2524453B2 JP2524453B2 (en) | 1996-08-14 |
Family
ID=15566966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4153641A Expired - Lifetime JP2524453B2 (en) | 1992-06-12 | 1992-06-12 | Thermosetting resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2524453B2 (en) |
Cited By (13)
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|---|---|---|---|---|
| WO2000055123A1 (en) * | 1999-03-12 | 2000-09-21 | Vantico Ag | Cyanate esters having flame resistant properties |
| US6194495B1 (en) | 1998-03-23 | 2001-02-27 | General Electric Company | Cyanate ester based thermoset compositions |
| US6245841B1 (en) | 1998-03-23 | 2001-06-12 | General Electric Company | Cyanate ester based thermoset compositions |
| JP2002309084A (en) * | 2001-04-12 | 2002-10-23 | Hitachi Chem Co Ltd | Siloxane-modified cyanate resin composition, adhesive film using the same, resin coated metal foil and multilayered printed circuit board |
| CN1101420C (en) * | 1997-11-25 | 2003-02-12 | 通用电气公司 | Poly (phenylene ether) thermoset compositions |
| JP2011202175A (en) * | 2011-05-27 | 2011-10-13 | Hitachi Chem Co Ltd | Siloxane-modified cyanate resin composition, adhesive film using the same, resin coated metal foil and multilayered printed wiring board |
| JP2012153808A (en) * | 2011-01-26 | 2012-08-16 | Sekisui Chem Co Ltd | Epoxy resin material and multilayer board |
| WO2014057051A1 (en) | 2012-10-12 | 2014-04-17 | Dsm Ip Assets B.V. | Composite antiballistic radome walls and methods of making the same |
| WO2015000926A1 (en) | 2013-07-02 | 2015-01-08 | Dsm Ip Assets B.V. | Composite antiballistic radome walls and methods of making the same |
| JP2017179014A (en) * | 2016-03-28 | 2017-10-05 | 味の素株式会社 | Resin composition |
| CN108395670A (en) * | 2018-03-12 | 2018-08-14 | 航天特种材料及工艺技术研究所 | A kind of preparation method of high temperature resistant EFFECTIVE MEDIUM sandwich layer |
| CN111454539A (en) * | 2020-04-17 | 2020-07-28 | 上海国瓷新材料技术有限公司 | Thermosetting resin composition and application thereof in millimeter wave circuit substrate |
| JP2021138803A (en) * | 2020-03-03 | 2021-09-16 | 住友ベークライト株式会社 | Resin composition, and carrier-attached resin film, prepreg, laminate, printed wiring board and semiconductor device including the same |
-
1992
- 1992-06-12 JP JP4153641A patent/JP2524453B2/en not_active Expired - Lifetime
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1101420C (en) * | 1997-11-25 | 2003-02-12 | 通用电气公司 | Poly (phenylene ether) thermoset compositions |
| US6194495B1 (en) | 1998-03-23 | 2001-02-27 | General Electric Company | Cyanate ester based thermoset compositions |
| US6245841B1 (en) | 1998-03-23 | 2001-06-12 | General Electric Company | Cyanate ester based thermoset compositions |
| WO2000055123A1 (en) * | 1999-03-12 | 2000-09-21 | Vantico Ag | Cyanate esters having flame resistant properties |
| US6458993B1 (en) | 1999-03-12 | 2002-10-01 | Vantico Inc. | Cyanate esters having flame resistant properties |
| JP2002539189A (en) * | 1999-03-12 | 2002-11-19 | バンティコ アクチエンゲゼルシャフト | Cyanate ester with flame resistance |
| KR100693368B1 (en) * | 1999-03-12 | 2007-03-12 | 훈츠만 어드밴스트 머티리얼스(스위처랜드)게엠베하 | Cyanate esters having flame resistant properties |
| JP2002309084A (en) * | 2001-04-12 | 2002-10-23 | Hitachi Chem Co Ltd | Siloxane-modified cyanate resin composition, adhesive film using the same, resin coated metal foil and multilayered printed circuit board |
| JP2012153808A (en) * | 2011-01-26 | 2012-08-16 | Sekisui Chem Co Ltd | Epoxy resin material and multilayer board |
| JP2011202175A (en) * | 2011-05-27 | 2011-10-13 | Hitachi Chem Co Ltd | Siloxane-modified cyanate resin composition, adhesive film using the same, resin coated metal foil and multilayered printed wiring board |
| WO2014057051A1 (en) | 2012-10-12 | 2014-04-17 | Dsm Ip Assets B.V. | Composite antiballistic radome walls and methods of making the same |
| US10062962B2 (en) | 2012-10-12 | 2018-08-28 | Dsm Ip Assets B.V. | Composite antiballistic radome walls and methods of making the same |
| WO2015000926A1 (en) | 2013-07-02 | 2015-01-08 | Dsm Ip Assets B.V. | Composite antiballistic radome walls and methods of making the same |
| US10153546B2 (en) | 2013-07-02 | 2018-12-11 | Dsm Ip Assets B.V. | Composite antiballistic radome walls and methods of making the same |
| JP2017179014A (en) * | 2016-03-28 | 2017-10-05 | 味の素株式会社 | Resin composition |
| CN108395670A (en) * | 2018-03-12 | 2018-08-14 | 航天特种材料及工艺技术研究所 | A kind of preparation method of high temperature resistant EFFECTIVE MEDIUM sandwich layer |
| CN108395670B (en) * | 2018-03-12 | 2020-07-10 | 航天特种材料及工艺技术研究所 | Preparation method of high-temperature-resistant equivalent medium core layer |
| JP2021138803A (en) * | 2020-03-03 | 2021-09-16 | 住友ベークライト株式会社 | Resin composition, and carrier-attached resin film, prepreg, laminate, printed wiring board and semiconductor device including the same |
| CN111454539A (en) * | 2020-04-17 | 2020-07-28 | 上海国瓷新材料技术有限公司 | Thermosetting resin composition and application thereof in millimeter wave circuit substrate |
| CN111454539B (en) * | 2020-04-17 | 2023-04-18 | 上海国瓷新材料技术有限公司 | Thermosetting resin composition and application thereof in millimeter wave circuit substrate |
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| Publication number | Publication date |
|---|---|
| JP2524453B2 (en) | 1996-08-14 |
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