JP2016026261A - 樹脂組成物、これを用いたプリプレグ、積層板及びプリント配線板 - Google Patents
樹脂組成物、これを用いたプリプレグ、積層板及びプリント配線板 Download PDFInfo
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- JP2016026261A JP2016026261A JP2015212319A JP2015212319A JP2016026261A JP 2016026261 A JP2016026261 A JP 2016026261A JP 2015212319 A JP2015212319 A JP 2015212319A JP 2015212319 A JP2015212319 A JP 2015212319A JP 2016026261 A JP2016026261 A JP 2016026261A
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- 150000003672 ureas Chemical class 0.000 description 1
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- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
1.(a)1分子構造中に少なくとも2個のN−置換マレイミド基を有するマレイミド化合物と、(b)1分子構造中に少なくとも1個のアミノ基を有するシリコーン化合物を含有することを特徴とする樹脂組成物。
2.さらに、(c)分子構造中にフェノール性水酸基を有する化合物を含有する上記1の樹脂組成物。
3.さらに、(d)熱硬化性樹脂を含有する上記1又は2の樹脂組成物。
4.(b)成分が、1分子構造中に少なくとも2個のアミノ基を有するシリコーン化合物である上記1〜3いずれかの樹脂組成物。
5.(b)成分が、両末端にアミノ基を有するシリコーン化合物である上記1〜3いずれかの樹脂組成物。
6.(b)成分が、どちらか一方の末端にアミノ基を有するシリコーン化合物である上記1〜3いずれかの樹脂組成物。
7.(b)成分が側鎖にアミノ基を有するシリコーン化合物である上記1〜3のいずれかの樹脂組成物。
8.(b)成分が、側鎖及び、少なくとも一方の末端にアミノ基を有するシリコーン化合物である上記1〜3いずれかの樹脂組成物。
9.(c)成分が、分子構造中にアミノ基とフェノール性水酸基を有する化合物である上記1〜8いずれかの樹脂組成物。
10.(c)成分が多官能フェノール性樹脂である上記1〜9いずれかの樹脂組成物。
11.(d)成分が、分子構造中にエポキシ基および/又はシアネート基を有する樹脂である上記1〜10いずれかの樹脂組成物。
12.さらに、下記一般式(I)又は(II)で表される(e)硬化促進剤を含有する上記1〜11のいずれかの樹脂組成物。
(式中、R6、R7、R8、R9はそれぞれ独立に、水素原子、炭素数1〜5の脂肪族炭化水素基、又はフェニル基を示し、Dはアルキレン基又は芳香族炭化水素基である。)
(式中、R6、R7、R8、R9は各々独立に水素原子、又は炭素数1〜5の脂肪族炭化水素基、フェニル基を示し、Bは単結合、又はアルキレン基、アルキリデン基、エーテル基、スルフォニル基のいずれかである。)
14.上記1〜13いずれかの樹脂組成物を用いたプリプレグ。
15.上記14のプリプレグを用いて積層成形して得られた積層板。
16.上記15の積層板を用いて製造されたプリント配線板。
(c)成分の分子構造中にフェノール性水酸基を有する化合物は、例えば、ビスフェノールA、ビスフェノールF、ビスフェノールS、4,4−ビフェニルフェノール、テトラメチルビスフェノールA、ジメチルビスフェノールA、テトラメチルビスフェノールF、ジメチルビスフェノールF、テトラメチルビスフェノールS、ジメチルビスフェノールS、テトラメチル4,4−ビフェノール、ジメチル−4、4−ビフェニルフェノール、1−(4−ヒドロキシフェニル)−2−[4−(1,1−ビス−(4−ヒドロキシフェニル)エチル)フェニル]プロパン、2,2−メチレン−ビス(4−メチル−6−tert−ブチルフェノール)、4,4−ブチリデン−ビス(3−メチル−6−tertブチルフェノール)、トリスヒドロキシフェニルメタン、レゾルシノール、ハイドロキノン、ピロガロール、ジイソプロポリデン骨格を有するフェノール類、1,1−ジ−4−ヒドロキシフェニルフルオレン等のフルオレン骨格を有するフェノール類、フェノール化ポリブタジエン、フェノール、クレゾール類、エチルフェノール類、ブチルフェノール類、オクチルフェノール類、ビスフェノールA、ビスフェノールF、ビスフェノールS、ナフトール類等の各種フェノールを原料とするノボラック樹脂、キシリレン骨格含有フェノールノボラック樹脂、ジシクロペンタジエン骨格含有フェノールノボラック樹脂、ビフェニル骨格含有フェノールノボラック樹脂、フルオレン骨格含有フェノールノボラック樹脂等の各種ノボラック樹脂が挙げられる。
2.0≦(マレイミド基当量)/(−NH2基換算の当量)≦10.0
に示す範囲であることが望ましい。当量比が10.0を超えると溶剤への溶解性が不足したり積層板の耐熱性が低下する場合があり、2.0未満であるとゲル化を起こしたり、積層板の耐熱性が低下する場合がある。
この反応で使用される有機溶剤は特に制限されないが、例えばエタノール、プロパノール、ブタノール、メチルセロソルブ、ブチルセロソルブ、プロピレングリコールモノメチルエーテル等のアルコール系溶剤、アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン等のケトン系溶剤、テトラヒドロフラン等のエーテル系溶剤、トルエン、キシレン、メシチレン等の芳香族系溶剤、ジメチルホルムアミド、ジメチルアセトアミド、N−メチルピロリドン等の窒素原子含有溶剤、ジメチルスルホキシド等の硫黄原子含有溶剤が挙げられ、これらは単独で、あるいは2種類以上を混合して使用してもよい。これらの中で、溶解性の点からシクロヘキサノン、プロピレングリコールモノメチルエーテル、メチルセロソルブが好ましく、低毒性である点からシクロヘキサノン、プロピレングリコールモノメチルエーテルがより好ましく、揮発性が高くプリプレグの製造時に残溶剤として残りにくいプロピレングリコールモノメチルエーテルが特に好ましい。
上記の(a)成分と(c)成分を有機溶剤中で反応させる際、反応温度は70〜150℃であることが好ましく、100〜130℃であることがさらに好ましい。反応時間は0.1〜10時間であることが好ましく、1〜6時間であることがさらに好ましい。
その中でもイミダゾール類及びその誘導体が耐熱性や難燃性、銅箔接着性等の点から好ましく、更に下記一般式(I)で表されるイソシアネート樹脂や、下記一般式(II)で表されるイミダゾール基がエポキシ樹脂によって置換された化合物によって置換された化合物が200℃以下での比較的低温での硬化成形性とワニスやプリプレグの経日安定性に優れるためより好ましく、具体的には下記式(III)又は式(IV)で表される化合物が少量の配合使用でよく、また商業的にも安価であることから特に好ましい。
(式中、R6、R7、R8、R9は各々独立に水素原子、又は炭素数1〜5の脂肪族炭化水素基、フェニル基を示し、Dはアルキレン基、芳香族炭化水素基である。)
(式中、R6、R7、R8、R9は各々独立に水素原子、又は炭素数1〜5の脂肪族炭化水素基、フェニル基を示し、Bは単結合、又はアルキレン基、アルキリデン基、エーテル基、スルフォニル基のいずれかである。)
熱可塑性樹脂の例としては、テトラフルオロエチレン、ポリエチレン、ポリプロピレン、ポリスチレン、ポリフェニレンエーテル樹脂、フェノキシ樹脂、ポリカーボネート樹脂、ポリエステル樹脂、ポリアミド樹脂、ポリイミド樹脂、キシレン樹脂、石油樹脂及びシリコーン樹脂が挙げられる。
エラストマーの例としては、ポリブタジエン、アクリロニトリル、エポキシ変性ポリブタジエン、無水マレイン酸変性ポリブタジエン、フェノール変性ポリブタジエン及びカルボキシ変性アクリロニトリルが挙げられる。
有機充填材の例としては、シリコーンパウダー、テトラフルオロエチレン、ポリエチレン、ポリプロピレン、ポリスチレン、並びにポリフェニレンエーテル等の有機物粉末が挙げられる。
ワニスは固形分濃度として40〜80質量%として使用することが好ましい。
本発明のプリプレグは、本発明の樹脂組成物を、基材に含浸又は塗工し、加熱等により半硬化(Bステージ化)して本発明のプリプレグを製造することができる。本発明の基材として、各種の電気絶縁材料用積層板に用いられている周知のものが使用できる。その材質の例としては、Eガラス、Dガラス、Sガラス及びQガラス等の無機物繊維、ポリイミド、ポリエステル及びテトラフルオロエチレン等の有機繊維、並びにそれらの混合物が挙げられる。
積層板を製造する際の成形条件は、例えば、電気絶縁材料用積層板及び多層板の手法が適用でき、例えば多段プレス、多段真空プレス、連続成形、オートクレーブ成形機等を使用し、温度100〜250℃、圧力0.2〜10MPa、加熱時間0.1〜5時間の範囲で成形することができる。また、本発明のプリプレグと内層用配線板とを組合せ、積層成形して、積層板を製造することもできる。
なお、各実施例および比較例得られた銅張積層板を用いて、ガラス転移温度、熱膨張率、はんだ耐熱性、そり特性について以下の方法で測定・評価した。
銅張積層板を銅エッチング液に浸漬することにより銅箔を取り除いた5mm角の評価基板を作製し、TMA試験装置(デュポン社製、TMA2940)を用いて圧縮法で熱機械分析をおこなった。評価基板を前記装置にZ方向に装着後、荷重5g、昇温速度10℃/分の測定条件にて連続して2回測定した。2回目の測定における熱膨張曲線の異なる接線の交点で示されるTgを求め、耐熱性を評価した。
(2)熱膨張率の測定
銅張積層板を銅エッチング液に浸漬することにより銅箔を取り除いた5mm角の評価基板を作製し、TMA試験装置(デュポン社製、TMA2940)を用いて圧縮法で熱機械分析をおこなった。評価基板を前記装置にX方向に装着後、荷重5g、昇温速度10℃/分の測定条件にて連続して2回測定した。2回目の測定における30℃から100℃の平均熱膨張率を算出し、これを熱膨張率の値とした。
5cm角の銅張積層板を作製し、温度288℃のはんだ浴に、評価基板を1分間浮かべた後、外観を観察することによりはんだ耐熱性を評価した。
AKROMETRIX社製 サーモレイPS200シャドーモアレ分析を用いて、基板の反り量を評価した。基板のサンプルサイズは40mm×40mmとし、測定エリアは36mm×36mmとした。室温から260℃まで加熱し、その後50℃まで冷却した時のそり量を測定した。
以下に示す(a)〜(d)成分と、(e)硬化促進剤、(f)無機充填材、及び希釈溶剤にメチルエチルケトンを使用して、第1表〜第3表に示した配合割合(質量部)で混合して樹脂分65質量%の均一なワニスを得た。
次に、上記ワニスを厚さ0.1mmのEガラスクロスに含浸塗工し、160℃で10分加熱乾燥して樹脂含有量50質量%のプリプレグを得た。
このプリプレグを4枚重ね、18μmの電解銅箔を上下に配置し、圧力2.5MPa、温度230℃で90分間プレスを行って、銅張積層板を得た。
得られた銅張積層板の測定・評価結果を第1表〜第3表に示す。
ビス(4−マレイミドフェニル)メタン
3、3−ジメチル−5、5−ジエチル−4、4−ジフェニルメタンビスマレイミド
(b)シリコーン化合物
X−22−161A(信越化学工業(株)製、アミン当量800)
X−22−161B(信越化学工業(株)製、アミン当量1500)
KF−8012(信越化学工業(株)製、アミン当量2200)
(c)フェノール性水酸基を有する化合物
ビスフェノールA
p−アミノフェノール
(d)熱硬化性樹脂
ビフェニルアラルキル型エポキシ樹脂(日本化薬(株)製、商品名:NC−3000−H)
ノボラック型シアネート樹脂(ロンザンジャパン(株)製、商品名:PT−30)
(e)硬化促進剤:G−8009L(ヘキサメチレンジイソシアネート樹脂と2−エチル−4−メチルイミダゾールの付加反応物:前記の式(III)で表される化合物)
(f)無機充填材:溶融シリカ((株)アドマテックス製、商品名:SC−2050KNK)
その他の化合物
ジアミノジフェニルメタン(比較例)
2、2−ビス[4−(アミノフェノキシ)フェニル]プロパン(比較例)
Claims (15)
- (a)1分子構造中に少なくとも2個のN−置換マレイミド基を有するマレイミド化合物と、(b)1分子構造中に少なくとも1個のアミノ基を有するシリコーン化合物を含有する樹脂組成物を用いたプリプレグ。
- 前記樹脂組成物が(c)分子構造中にフェノール性水酸基を有する化合物を含有する、請求項1に記載のプリプレグ。
- 前記(c)成分が、分子構造中にアミノ基とフェノール性水酸基を有する化合物である、請求項2に記載のプリプレグ。
- 前記(c)成分が多官能フェノール性樹脂である、請求項2に記載のプリプレグ。
- 前記樹脂組成物が(d)熱硬化性樹脂を含有する、請求項1〜4のいずれか一項に記載のプリプレグ。
- 前記(d)成分が、分子構造中にエポキシ基および/又はシアネート基を有する樹脂である、請求項5に記載のプリプレグ。
- 前記(b)成分が、1分子構造中に少なくとも2個のアミノ基を有するシリコーン化合物である、請求項1〜6のいずれか一項に記載のプリプレグ。
- 前記(b)成分が、両末端にアミノ基を有するシリコーン化合物である、請求項1〜6のいずれか一項に記載のプリプレグ。
- 前記(b)成分が、どちらか一方の末端にアミノ基を有するシリコーン化合物である、請求項1〜6のいずれか一項に記載のプリプレグ。
- 前記(b)成分が側鎖にアミノ基を有するシリコーン化合物である、請求項1〜6のいずれか一項に記載のプリプレグ。
- 前記(b)成分が、側鎖及び、少なくとも一方の末端にアミノ基を有するシリコーン化合物である、請求項1〜6のいずれか一項に記載のプリプレグ。
- 前記樹脂組成物が下記一般式(I)又は(II)で表される(e)硬化促進剤を含有する、請求項1〜11のいずれか一項に記載のプリプレグ。
(式中、R6、R7、R8、R9はそれぞれ独立に、水素原子、炭素数1〜5の脂肪族炭化水素基、又はフェニル基を示し、Dはアルキレン基又は芳香族炭化水素基である。)
(式中、R6、R7、R8、R9は各々独立に水素原子、又は炭素数1〜5の脂肪族炭化水素基、フェニル基を示し、Bは単結合、又はアルキレン基、アルキリデン基、エーテル基、スルフォニル基のいずれかである。) - 前記樹脂組成物が(f)無機充填材を含有する、請求項1〜12のいずれか一項に記載のプリプレグ。
- 請求項1〜13のいずれか一項に記載のプリプレグを用いて積層成形して得られた積層板。
- 請求項14に記載の積層板を用いて製造されたプリント配線板。
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WO2017150587A1 (ja) | 2016-03-02 | 2017-09-08 | Jnc株式会社 | 低熱膨張部材用組成物、低熱膨張部材、電子機器、低熱膨張部材の製造方法 |
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KR20180085043A (ko) | 2018-07-25 |
EP2666826A1 (en) | 2013-11-27 |
KR20140006825A (ko) | 2014-01-16 |
WO2012099134A1 (ja) | 2012-07-26 |
US9133308B2 (en) | 2015-09-15 |
TW201251531A (en) | 2012-12-16 |
JP5831463B2 (ja) | 2015-12-09 |
CN103328578A (zh) | 2013-09-25 |
CN103328578B (zh) | 2015-06-17 |
KR102138449B1 (ko) | 2020-07-27 |
US20140000948A1 (en) | 2014-01-02 |
EP2666826A4 (en) | 2014-07-02 |
KR102082518B1 (ko) | 2020-02-27 |
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JPWO2012099134A1 (ja) | 2014-06-30 |
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