JP6278218B2 - 樹脂組成物、プリプレグ及び積層板 - Google Patents
樹脂組成物、プリプレグ及び積層板 Download PDFInfo
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- JP6278218B2 JP6278218B2 JP2016231008A JP2016231008A JP6278218B2 JP 6278218 B2 JP6278218 B2 JP 6278218B2 JP 2016231008 A JP2016231008 A JP 2016231008A JP 2016231008 A JP2016231008 A JP 2016231008A JP 6278218 B2 JP6278218 B2 JP 6278218B2
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- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
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- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
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- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
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- 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
- H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
- H05K2201/01—Dielectrics
- H05K2201/0104—Properties and characteristics in general
- H05K2201/012—Flame-retardant; Preventing of inflammation
-
- 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
- H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
- H05K2201/02—Fillers; Particles; Fibers; Reinforcement materials
- H05K2201/0203—Fillers and particles
- H05K2201/0206—Materials
- H05K2201/0209—Inorganic, non-metallic particles
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
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- Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
-
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- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
- Y10T428/24917—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.] including metal layer
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
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Description
<1> フェノール変性キシレンホルムアルデヒド樹脂をシアネート化したシアン酸エステル化合物(A)、エポキシ樹脂(B)及び無機充填材(C)を少なくとも含有する、
プリプレグ用樹脂組成物。
<2> 前記シアン酸エステル化合物(A)が、下記一般式(I)で表される構造を有する、
上記<1>に記載のプリプレグ用樹脂組成物。
<3> 前記エポキシ樹脂(B)が、下記一般式(10)で表されるビフェニルアラルキル型エポキシ樹脂及び/又は下記一般式(11)で表されるナフタレン骨格を有するエポキシ樹脂である、
上記<1>又は<2>に記載のプリプレグ用樹脂組成物。
上記<1>〜<3>のいずれか一項に記載のプリプレグ用樹脂組成物。
<5> 前記シアン酸エステル化合物(A)が、前記(A)成分と前記(B)成分の合計100質量部に対して、30〜70質量部含まれる、
上記<1>〜<4>のいずれか一項に記載のプリプレグ用樹脂組成物。
<6> 前記エポキシ樹脂(B)が、前記(A)成分と前記(B)成分の合計100質量部に対して、30〜70質量部含まれる、
上記<1>〜<5>のいずれか一項に記載のプリプレグ用樹脂組成物。
<7> 前記無機充填材(C)が、前記(A)成分と前記(B)成分の合計100質量部に対して、10〜300質量部含まれる、
上記<1>〜<6>のいずれか一項に記載のプリプレグ用樹脂組成物。
<9> 上記<8>に記載のプリプレグが複数積層した積層板。
<10> 上記<8>に記載のプリプレグと、前記プリプレグ上に積層された金属箔とを有する金属箔張り積層板。
<11> 上記<8>に記載の積層板を有するプリント配線板。
<12> 絶縁層と、前記絶縁層の表面に形成された導体層とを含むプリント配線板であって、前記絶縁層が、上記<1>〜<7>のいずれか一項に記載のプリプレグ用樹脂組成物を含むプリント配線板。
フェノール変性キシレンホルムアルデヒド樹脂(ニカノールGLP)をシアネート化したシアン酸エステル化合物(下記一般式(Ia)のシアン酸エステル(代表組成として下記式(14)を有する):以下、GLPCと略す)の合成
フェノール800g(8.5mol)及び触媒のPTSA(パラトルエンスルホン酸)0.43gを仕込み撹拌昇温し、液温130℃にてキシレンホルムアルデヒド樹脂(ニカノールG、フドー(株)製)670gを1時間かけて滴下した。滴下中、還流温度は150℃から105℃に低下する。滴下後1時間で反応を完結させた。反応後、脱フェノールするため水蒸気蒸留を170℃で2.5時間実施した。その後冷却しながら徐々にメチルイソブチルケトン1700gを添加し希釈した。次いで、希釈した反応液を、70〜80℃の温水850gで3回繰り返し洗浄した。
上記方法で得られた一般式(Ia’)で表されるフェノール変性キシレンホルムアルデヒド樹脂(ニカノールGLP)20g(OH基として0.112mol)及びトリエチルアミン17.13g(0.168mol)を塩化メチレン120gに溶解させた(溶液1)。0.249molの塩化シアンの塩化メチレン溶液48.1gと36%塩酸23.76g(0.235mol)と水147.3gを撹拌混合した溶液へ、−5〜+5℃で溶液1を10分かけて滴下した。30分撹拌した後、トリエチルアミン11.42g(0.112mol)と塩化メチレン11.4gの混合溶液を滴下し、さらに30分撹拌して反応を完結させた。反応液を分液し、有機相を分取した。得られた有機相を水100gで4回洗浄した後、蒸留により塩化メチレンを留去し、目的とする上記式(Ia)で表されるフェノール変性キシレンホルムアルデヒド樹脂のシアン酸エステル(GLPC)23.1gを黄赤色粘性物として得た。
2,6−キシレノール変性キシレンホルムアルデヒド樹脂をシアネート化したシアン酸エステル化合物(下記一般式(Ib)のシアン酸エステル(代表組成として下記式(15)を有する:以下、NXDCと略す))の合成
2,6−キシレノール486.8g(3.99mol)及び触媒のPTSA(パラトルエンスルホン酸)6.3gを仕込み攪拌昇温し、液温125℃になった時点でキシレンホルムアルデヒド樹脂(ニカノールGL16、フドー(株)製)144gを1時間かけて滴下した。滴下中、昇温を続け、150℃、3時間で反応を完結させた。反応後120℃以下に冷却し、反応液にメタキシレン160gを添加し、次にメチルイソブチルケトン240gを添加し反応液を希釈した。次いで、希釈した反応液を、70〜80℃の温水400gで3回繰り返し洗浄した。
上記方法で得られた一般式(Ib’)で表される2,6−キシレノール変性キシレンホルムアルデヒド樹脂の精製品256g(OH基として1.45mol)及び1.6molトリエチルアミンを3−メチルテトラヒドロフラン600mLに溶解させた(溶液2)。その後、2.8molの塩化シアンの塩化メチレン溶液500gに−10℃で溶液2を1.5時間かけて滴下した。30分撹拌した後、0.8molのトリエチルアミンと塩化メチレン115gの混合溶液を滴下し、さらに30分撹拌して反応を完結させた。そして、反応液からトリエチルアミンの塩酸塩を濾別し、得られたろ液を0.1N塩酸1000mLにより洗浄した後、さらにNaCl水溶液1000mLで3回洗浄し、最後に水1000mLによる洗浄を行った。得られた塩化メチレン溶液を硫酸ナトリウムにより乾燥し、蒸留操作により塩化メチレンを留去することにより、目的とする上記式(Ib)で表される2,6−キシレノール変性キシレンホルムアルデヒド樹脂のシアン酸エステル(NXDC)240gを黄赤色粘性物として得た。
ビフェニルアラルキル型シアン酸エステル化合物の合成
ビフェニルアラルキル型フェノール樹脂(KAYAHARD GPH65、日本化薬(株)製)0.50モルをクロロホルム500mlに溶解後、0.75molのトリエチルアミンを添加混合し、これに1.0モルの塩化シアンを溶解したクロロホルム溶液300gを−10℃で1.5時間かけて滴下した。30分撹拌した後、0.1モルのトリエチルアミンとクロロホルム30gの混合溶液を滴下し、さらに30分撹拌して反応を完結させた。そして、生成するトリエチルアミンの塩酸塩を反応液から濾別し、得られたろ液を0.1N塩酸500mLにより洗浄した後、さらに水500mLによる洗浄を4回繰り返した。これを硫酸ナトリウムによって乾燥した後、濃縮することで、結晶を得た。得られた結晶をn−ヘキサン1000mLにて洗浄した後、減圧乾燥することにより、ビフェニルアラルキル型のシアン酸エステルを得た。このようにして得られたビフェニルアラルキル型シアン酸エステル化合物は、赤外吸収スペクトル測定の結果、フェノール性OH基に起因する3200〜3600cm-1の吸収スペクトルが消失し、シアン酸エステルのニトリルに起因する2264cm-1付近の吸収スペクトルを有することが確認された。
合成例1で得たGLPC50質量部をメチルエチルケトンで溶解した後、同じくメチルエチルケトンで溶解させたフェノールビフェニルアラルキル型エポキシ樹脂(NC3000−H、日本化薬(株)製)50質量部を混合して樹脂組成物を調製した。この樹脂のみの樹脂組成物は、目視で透明であり、樹脂が溶媒に溶解した状態であることが確認された。次に、この樹脂組成物に球状合成シリカ(SC−2050MR、(株)アドマテックス製)を150部混合し、さらにオクチル酸亜鉛0.04質量部を混合することにより、樹脂組成物(ワニス)を調製した。
このようにして得られたワニスをメチルエチルケトンで希釈し、これを厚さ0.1mmのEガラスクロスに含浸塗工し、165℃で10.5分間加熱乾燥することにより、樹脂含有量が37質量%のプリプレグを作製し。次に、プリプレグを4枚重ね合わせ、得られた積層体の両面に厚さ18μmの電解銅箔を配置し、圧力30kgf/cm2、温度220℃、120分間の真空プレスを行い積層形成することで、絶縁層厚さ0.4mmの金属箔張り積層板(両面銅張積層板)を作製した。得られた両面銅張積層板の物性測定結果を表1に示す。
GLPC50質量部に代えて、合成例2で得たNXDC50質量部を用いること以外は、実施例1と同様に行った。樹脂のみのワニスは、目視で透明であり、樹脂が溶媒に溶解した状態であることが確認された。得られた両面銅張積層板の物性測定結果を表1に示す。
GLPC50質量部に代えて、2,2−ビス(4−シアネートフェニル)プロパンのプレポリマー(CA210、三菱ガス化学(株)製)50質量部を用いること以外は、実施例1と同様に行った。樹脂のみのワニスは、目視で透明であり、樹脂が溶媒に溶解した状態であることが確認された。得られた両面銅張積層板の物性測定結果を表1に示す。
GLPC50質量部に代えて、フェノールノボラック型シアン酸エステル化合物(PrimasetPT−30、ロンザ社製)50質量部を用いること以外は、実施例1と同様に行った。樹脂のみのワニスは、目視で透明であり、樹脂が溶媒に溶解した状態であることが確認された。得られた両面銅張積層板の物性測定結果を表1に示す。
GLPC50質量部に代えて、比較合成例1で得たビフェニルアラルキル型シアン酸エステル化合物50質量部を用いること以外は、実施例1と同様に行った。なお、この比較合成例1で得たビフェニルアラルキル型シアン酸エステルは、メチルエチルケトンに溶解せず、樹脂のみのワニスはミキサーにて撹拌後も不溶物によって懸濁した状態であったが、そのまま球状合成シリカ等を加えてワニスを調製し、ガラスクロスへの含浸塗工を同様に行った。得られた両面銅張積層板の物性測定結果を表1に示す。
銅張積層板の銅箔をエッチングによって除去した後、吸水性と耐燃性の評価をおこなった。
1)吸水率:得られた両面銅張積層板をダイシングソーで50mm×50mm×0.4mmのサイズに切断し、両面の銅箔をエッチングによりすべて除去して得たサンプルを用い、JIS−C6481に準拠して行った。具体的には、まず、50℃で24時間乾燥後の重量を測定し(W0)、次に、プレッシャークッカー試験機(平山製作所製、PC3型)を用いて121℃、2気圧で3時間吸水させた後の重量を測定し(W1)、吸水率を下記式に基づいて算出した。
吸水率(wt%)=100×(W1−W0)/W0
2)耐燃性:得られた両面銅張積層板をダイシングソーで13mm×130mm×0.4mmのサイズに切断し、両面の銅箔をエッチングによりすべて除去して得たサンプルを用い、UL94垂直燃焼試験法に準拠して耐燃性試験を実施した。
Claims (10)
- フェノール変性キシレンホルムアルデヒド樹脂をシアネート化したシアン酸エステル化合物(A)、エポキシ樹脂(B)及び無機充填材(C)を少なくとも含有し、
前記無機充填材(C)が、前記(A)成分と前記(B)成分の合計100質量部に対して、10〜300質量部含まれ、
前記エポキシ樹脂(B)が、下記一般式(10)で表されるビフェニルアラルキル型エポキシ樹脂及び/又は下記一般式(11)で表されるナフタレン骨格を有するエポキシ樹脂である、
プリプレグ用樹脂組成物。 - 前記シアン酸エステル化合物(A)が、下記一般式(I)で表される構造を有する、
請求項1に記載のプリプレグ用樹脂組成物。 - 前記無機充填材(C)が、シリカである、
請求項1又は2に記載のプリプレグ用樹脂組成物。 - 前記シアン酸エステル化合物(A)が、前記(A)成分と前記(B)成分の合計100質量部に対して、30〜70質量部含まれる、
請求項1〜3のいずれか一項に記載のプリプレグ用樹脂組成物。 - 前記エポキシ樹脂(B)が、前記(A)成分と前記(B)成分の合計100質量部に対して、30〜70質量部含まれる、
請求項1〜4のいずれか一項に記載のプリプレグ用樹脂組成物。 - 請求項1〜5のいずれか一項に記載のプリプレグ用樹脂組成物を基材に含浸又は塗布してなる
プリプレグ。 - 請求項6に記載のプリプレグが複数積層した
積層板。 - 請求項7に記載のプリプレグと、前記プリプレグ上に積層された金属箔とを有する
金属箔張り積層板。 - 請求項8に記載の金属箔張り積層板を有する
プリント配線板。 - 絶縁層と、前記絶縁層の表面に形成された導体層とを含むプリント配線板であって、
前記絶縁層が、請求項1〜5のいずれか一項に記載のプリプレグ用樹脂組成物を含む
プリント配線板。
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JP2017048399A (ja) | 2017-03-09 |
EP2789637A4 (en) | 2015-07-22 |
WO2013084819A1 (ja) | 2013-06-13 |
US9706651B2 (en) | 2017-07-11 |
TW201329120A (zh) | 2013-07-16 |
KR101969191B1 (ko) | 2019-04-15 |
KR20140109376A (ko) | 2014-09-15 |
EP2789637A1 (en) | 2014-10-15 |
CN103987753B (zh) | 2016-06-08 |
TWI555766B (zh) | 2016-11-01 |
CN103987753A (zh) | 2014-08-13 |
JPWO2013084819A1 (ja) | 2015-04-27 |
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US20140329066A1 (en) | 2014-11-06 |
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