JP2012219232A - 難燃性熱硬化性樹脂組成物、その硬化物及びそれを用いたプリント配線板 - Google Patents
難燃性熱硬化性樹脂組成物、その硬化物及びそれを用いたプリント配線板 Download PDFInfo
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- JP2012219232A JP2012219232A JP2011088927A JP2011088927A JP2012219232A JP 2012219232 A JP2012219232 A JP 2012219232A JP 2011088927 A JP2011088927 A JP 2011088927A JP 2011088927 A JP2011088927 A JP 2011088927A JP 2012219232 A JP2012219232 A JP 2012219232A
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- PWZFXELTLAQOKC-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide;tetrahydrate Chemical compound O.O.O.O.[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O PWZFXELTLAQOKC-UHFFFAOYSA-A 0.000 description 5
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
Abstract
【解決手段】難燃性熱硬化性樹脂組成物は、(A)熱分解開始温度が260℃未満のカルボキシル基含有樹脂、(B)熱分解開始温度が260℃以上のカルボキシル基含有樹脂、(C)難燃性化合物、(D)酸化チタン、及び(E)熱硬化性成分を含有する組成物であって、前記熱分解開始温度が260℃未満のカルボキシル基含有樹脂(A)と熱分解開始温度が260℃以上のカルボキシル基含有樹脂(B)の比率が質量基準で50〜80:50〜20の範囲にある。好適には、前記カルボキシル基含有樹脂(A)は芳香環を有せず、前記カルボキシル基含有樹脂(B)は芳香環を有する。
【選択図】なし
Description
上記提案のように、塩素法により製造されたルチル型酸化チタンを用いた場合、光活性を殆ど有さないために、酸化チタンの光活性に起因する光による樹脂の劣化(黄変)が抑制され、光に対して優れた安定性を示す。しかしながら、ルチル型酸化チタンは、同じ酸化チタンであるアナターゼ型酸化チタンと比較して白色度が劣るため、白色硬化性樹脂組成物の難燃化も併せて達成しようとした場合、難燃性、柔軟性と高反射率を高いレベルでバランス良く達成することが難しいという問題がある。
さらに本発明の目的は、かかる硬化性樹脂組成物を用いることによって、高反射率を有し、且つ低変化率、柔軟性に優れた難燃性の白色硬化皮膜及びこのような優れた特性の難燃性硬化皮膜を有するプリント配線板を提供することにある。
ここで、熱分解開始温度とは、一定速度で昇温した時の重量減少を示差熱熱重量同時測定装置(TG/DTA)によって測定した重量減少開始時の温度をいう。
さらに本発明によれば、該硬化物からなる絶縁層又は保護膜を有するプリント配線板も提供される。
熱分解開始温度が260℃未満であるか、260℃以上であるかの一つの目安としては、カルボキシル基含有樹脂が芳香環を有しているか否かにより概略判断でき、カルボキシル基含有樹脂が芳香環を有していない場合には熱分解開始温度は260℃未満となり易く、カルボキシル基含有樹脂が芳香環を有している場合には熱分解開始温度は260℃以上となり易い。従って、好適には、熱分解開始温度が260℃未満のカルボキシル基含有樹脂(A)として、芳香環を含有していないカルボキシル基含有樹脂を選択し、熱分解開始温度が260℃以上のカルボキシル基含有樹脂(B)として、芳香環を含有するカルボキシル基含有樹脂を選択し、前記した割合で配合し、また、難燃性化合物(C)として、水酸化物(水酸化アルミニウム、水酸化マグネシウム等)とリン化合物(ホスファゼン、ホスフィン酸金属塩等)を併用し、さらに、酸化チタン(D)としてルチル型酸化チタンを組み合わせて用いることが最も好ましい。
以下、本発明の熱硬化性樹脂組成物の各構成成分について詳しく説明する。
このような熱分解開始温度が260℃未満のカルボキシル基含有樹脂(A)は、単独で又は2種以上を組み合わせて用いることができる。
なお、本明細書において、(メタ)アクリレートとは、アクリレート、メタクリレート及びそれらの混合物を総称する用語であり、他の類似の表現についても同様である。
(1)脂肪族不飽和カルボン酸と炭素数2〜20の脂肪族重合性モノマー(具体的には、脂肪族(メタ)アクリロイル化合物、脂肪族ビニルエーテル、脂肪酸のビニルエステルなどが挙げられる)の共重合によって得られるカルボキシル基含有樹脂、
(2)炭素数2〜20の脂肪族重合性モノマーから生成されるカルボキシル基含有(メタ)アクリル系共重合樹脂と、1分子中にオキシラン環とエチレン性不飽和基を有する炭素数4〜20の脂肪族重合性モノマーとの反応により得られる感光性のカルボキシル基含有樹脂、
(3)1分子中にそれぞれ1個のエポキシ基と不飽和二重結合を有する炭素数4〜20の脂肪族重合性モノマー(例えば、グリシジル(メタ)アクリレートなど)と、不飽和二重結合を有する炭素数2〜20の脂肪族重合性モノマー(具体的には、脂肪族(メタ)アクリロイル化合物、脂肪族ビニルエーテル、脂肪酸のビニルエステルなどが挙げられる。)との共重合体に、脂肪族不飽和モノカルボン酸を反応させ、生成した第2級の水酸基に飽和または不飽和の脂肪族多塩基酸無水物を反応させて得られる感光性のカルボキシル基含有樹脂、
(4)脂肪族水酸基含有ポリマーに、飽和または不飽和の脂肪族多塩基酸無水物を反応させた後、生成したカルボン酸に、1分子中にそれぞれ1個のエポキシ基と不飽和二重結合を有する炭素数4〜20の脂肪族重合性モノマー(例えば、グリシジル(メタ)アクリレートなど)を反応させて得られる感光性の水酸基及びカルボキシル基含有樹脂
である。
なお、本明細書中において、脂肪族とは、分子内にシクロヘキサン環やシクロヘキセン環などのシクロ環を含む化合物も含む。
また、前記カルボキシル基含有樹脂(B)の重量平均分子量は、樹脂骨格により異なるが、一般的に2,000〜150,000、さらには5,000〜100,000の範囲にあるものが好ましい。また、上記カルボキシル基含有樹脂は、前記列挙したものに限らず使用することができ、1種類でも2種以上を混合しても使用することができる。
また、前記したようなカルボキシル基含有樹脂(A)及び(B)の配合量(総量)は、組成物全体量の50wt%以下、好ましくは10〜40wt%の範囲が適当である。
リン元素含有アクリレートは、リン元素を有しており、分子中に複数の(メタ)アクリレートを含む化合物が良く、具体的には、前記一般式(II)におけるR3とR4が水素原子であり、R5がアクリレート誘導体である化合物が挙げられ、一般に、9,10−ジヒドロ−9−オキサ−10−フォスファフェナンスレン−10−オキサイドと公知慣用の多官能アクリレートモノマーとのマイケル付加反応により合成することができる。
このフェノール性水酸基を有するリン化合物は、疎水性、耐熱性が高く、加水分解による電気特性の低下が無く、はんだ耐熱性が高い。また、好適な組み合わせとして、熱硬化性成分としてビフェニル骨格を有するエポキシ樹脂やその他のエポキシ樹脂を使用することによって、エポキシ樹脂と反応し、ネットワークに取り込まれるので、硬化後にブリードアウトすることが無いという利点が得られる。市販品としては、三光(株)製HCA−HQなどがある。
オリゴマーもしくはポリマーであるリン化合物は、アルキル鎖の影響により折り曲げ性の低下が少なく、また分子量が大きいため硬化後のブリードアウトが無いという利点が得られる。市販品としては、三光(株)製M−Ester−HP、東洋紡(株)製バイロン337などがある。
フォスファゼンオリゴマーとしてはフェノキシフォスファゼン化合物が有効であり、置換もしくは無置換フェノキシフォスファゼンオリゴマー又は3量体、4量体、5量体の環状物があり、液状や固体粉末のものがあるがいずれも好適に使用することができる。市販品としては、(株)伏見製薬所製FP−100、FP−300、FP−390などがある。
過酸化物分解剤は市販のものであってもよく、例えば、アデカスタブTPP(ADEKA社製)、マークAO−412S(アデカ・アーガス化学社製)、スミライザー(登録商標)TPS(住友化学社製)等が挙げられる。
上記のような酸化防止剤は、1種を単独で又は2種以上を組み合わせて用いることができる。
このような紫外線吸収剤としては、ベンゾフェノン誘導体、ベンゾエート誘導体、ベンゾトリアゾール誘導体、トリアジン誘導体、ベンゾチアゾール誘導体、シンナメート誘導体、アントラニレート誘導体、ジベンゾイルメタン誘導体等が挙げられる。
測定サンプル:ガラス板に樹脂を塗布し、100℃で30分乾燥した塗膜。
測定機器:セイコーインスツールメント社製TG/DTA 6200。
測定範囲:30℃〜800℃。
昇温速度:10℃/分。
合成例1
撹拌装置、温度計、コンデンサーを備えた反応容器に、2つ以上のアルコール性ヒドロキシル基を有する化合物として1,5−ペンタンジオールと1,6−ヘキサンジオールから誘導されるポリカーボネートジオール(旭化成ケミカルズ(株)T5650J、数平均分子量800)を2400g(3.0モル)、ジメチロールブタン酸を603g(4.5モル)、及びモノヒドロキシル化合物として2−ヒドロキシエチルアクリレートを238g(2.6モル)投入した。次に、芳香族系でないイソシアネート基を有する化合物としてイソホロンジイソシアネート1887g(8.5モル)を投入し、撹拌しながら60℃まで加熱して停止し、反応容器内の温度が低下し始めた時点で再度加熱して80℃で撹拌を続け、赤外線吸収スペクトルでイソシアネート基の吸収スペクトル(2280cm−1)が消失したことを確認して反応を終了した。次いで、固形分が50wt%となるようにカルビトールアセテートを添加し、希釈剤を含有する粘稠液体のカルボキシル基含有ウレタン樹脂(A−1)を得た。得られたカルボキシル基含有ウレタン樹脂の固形分の酸価は51.0mgKOH/gであった。また、得られた樹脂について前記方法で測定した熱解開始温度は約250℃であった。
撹拌装置、温度計、コンデンサーを備えた反応容器に、2つ以上のアルコール性ヒドロキシル基を有する化合物として1,5−ペンタンジオールと1,6−ヘキサンジオールから誘導されるポリカーボネートジオール(旭化成ケミカルズ(株)T5650J、数平均分子量800)を2400g(3.0モル)、ジメチロールブタン酸を603g(4.5モル)、及びモノヒドロキシル化合物として2−ヒドロキシエチルアクリレートを238g(2.6モル)投入した。次に、芳香族系でないイソシアネート基を有する化合物としてトリメチルヘキサメチレンジイソシアネート1554g(7.0モル)を投入し、撹拌しながら60℃まで加熱して停止し、反応容器内の温度が低下し始めた時点で再度加熱して80℃で撹拌を続け、赤外線吸収スペクトルでイソシアネート基の吸収スペクトル(2280cm−1)が消失したことを確認して反応を終了した。次いで、固形分が50wt%となるようにカルビトールアセテートを添加し、希釈剤を含有する粘稠液体のカルボキシル基含有ウレタン樹脂(A−2)を得た。得られたカルボキシル基含有ウレタン樹脂の固形分の酸価は49.8mgKOH/gであった。また、得られた樹脂について前記方法で測定した熱解開始温度は約250℃であった。
攪拌機、温度計、還流冷却器、滴下ロート及び窒素導入管を備えた2リットルセパラブルフラスコに、溶媒としてジエチレングリコールジメチルエーテル900g、及び重合開始剤としてt−ブチルパーオキシ2−エチルヘキサノエート(日本油脂(株)製パーブチルO)21.4gを加えて90℃に加熱した。加熱後、ここに、メタクリル酸309.9g、メタクリル酸メチル116.4g、及びラクトン変性2−ヒドロキシエチルメタクリレート(ダイセル化学工業(株)製プラクセルFM1)109.8gを、重合開始剤であるビス(4−t−ブチルシクロヘキシル)パーオキシジカーボネート(日本油脂(株)製パーロイルTCP)21.4gと共に3時間かけて滴下して加え、さらに6時間熟成することにより、カルボキシル基含有共重合樹脂を得た。なお、反応は、窒素雰囲気下で行った。
次に、得られたカルボキシル基含有共重合樹脂に、3,4−エポキシシクロヘキシルメチルアクリレート(ダイセル化学(株)製サイクロマーA200)363.9g、開環触媒としてジメチルベンジルアミン3.6g、重合抑制剤としてハイドロキノンモノメチルエーテル1.80gを加え、100℃に加熱し、攪拌することによりエポキシの開環付加反応を行った。16時間後、固形分の酸価が108.9mgKOH/g、重量平均分子量が25,000の、芳香環を有さないカルボキシル基含有樹脂を53.8重量%(不揮発分)含む溶液を得た。以下、この反応溶液を樹脂(A−3)と呼ぶ。また、得られた樹脂について前記方法で測定した熱解開始温度は約190℃であった。
合成例4
ジエチレングリコールモノエチルエーテルアセテート600gにオルソクレゾールノボラック型エポキシ樹脂[DIC(株)製、EPICLON N−695、軟化点95℃、エポキシ当量214、平均官能基数7.6]1070g(グリシジル基数(芳香環総数):5.0モル)、アクリル酸360g(5.0モル)、及びハイドロキノン1.5gを仕込み、100℃に加熱攪拌し、均一溶解した。次いで、トリフェニルホスフィン4.3gを仕込み、110℃に加熱して2時間反応後、120℃に昇温してさらに12時間反応を行った。得られた反応液に芳香族系炭化水素(ソルベッソ150)415g、テトラヒドロ無水フタル酸456.0g(3.0モル)を仕込み、110℃で4時間反応を行い、冷却後、固形分酸価89mgKOH/g、固形分65%の樹脂溶液を得た。これを樹脂(B−1)とする。また、得られた樹脂について前記方法で測定した熱分解開始温度は約300℃であった。
エポキシ当量800、軟化点79℃のビスフェノールF型固型エポキシ樹脂400部をエピクロルヒドリン925部とジメチルスルホキシド462.5部を溶解させた後、攪拌下70℃で98.5%NaOH 81.2部を100分かけて添加した。添加後さらに70℃で3時間反応を行なった。次いで過剰の未反応エピクロルヒドリン及びジメチルスルホキシドの大半を減圧下に留去し、副生塩とジメチルスルホキシドを含む反応生成物をメチルイソブチルケトン750部に溶解させ、さらに30%NaOH 10部を加え70℃で1時間反応させた。反応終了後、水200部で2回水洗を行った。油水分離後、油層よりメチルイソブチルケトンを蒸留回収して、エポキシ当量290、軟化点62℃のエポキシ樹脂(a−1)370部を得た。エポキシ樹脂(a−1)2900部(10当量)、アクリル酸720部(10当量)、メチルハイドロキノン2.8部、カルビトールアセテート1950部を仕込み、90℃に加熱、攪拌し、反応混合物を溶解した。次いで、反応液を60℃に冷却し、トリフェニルフォスフィン16.7部を仕込み、100℃に加熱し、約32時間反応し、酸価が1.0mgKOH/gの反応物を得た。次に、これに無水コハク酸786部(7.86モル)、カルビトールアセテート423部を仕込み、95℃に加熱し、約6時間反応を行い、固形分酸価100mgKOH/g、固形分65%の樹脂溶液を得た。これを樹脂溶液(B−2)とする。また、得られた樹脂について前記方法で測定した熱分解開始温度は約340℃であった。
下記表1に示す種々の成分を表1に示す割合(質量部)にて配合し、攪拌機にて予備混合した後、3本ロールミルで混練し、熱硬化性樹脂組成物のペーストを調製した。
得られた熱硬化性樹脂組成物のペーストをスクリーン印刷にて硬化皮膜の膜厚が約15μmとなるように基板に塗工し、150℃で60分間熱硬化を行ない、試験基板を作製した。
<耐熱性>
各試験基板について、コニカミノルタ社製色彩色差計CR−400を用い、XYZ表色系のY値の初期値とL*a*b*表色系のL*、a*、b*の初期値を測定した。その後、各試験基板を150℃の熱風循環式乾燥炉に50時間放置して加速劣化させ、再度、ミノルタ製色彩色差計CR−400で各数値を測定しY値の変化とΔE*abで評価した。その結果を、目視による変色の評価結果と共に表2に示す。
ΔE*ab=[(L*2−L*1)2+(a*2−a*1)2+(b*2−b*1)2]1/2
式中、L*1、a*1、b*1は、各々L*、a*、b*の初期値を表し、L*2、a*2、b*2は、各々加速劣化後のL*、a*、b*の値を表す。
○:まったく変色がない。
△:少し変色がある。
×:変色がある。
各熱硬化性樹脂組成物のペーストを、100メッシュポリエステル版で、12.5μm厚ポリイミドフィルム[カプトン(登録商標)50H、東レ・デュポン(株)製]にスクリーン印刷により塗布し、150℃で30分熱硬化した。なお、硬化後のペースト膜厚は約15μmに調整した。
ペーストを塗布・熱硬化したポリイミドフィルムを、塗布面を外側にし、5.0mmφの円柱に密着するように巻きつけ、目視で観察した結果を、以下の基準でベンデング性を評価した。
○:硬化皮膜にクラックがないもの。
×:硬化皮膜にクラックがあるもの。
各熱硬化性樹脂組成物のペーストを、100メッシュポリエステル版で、12.5μm厚ポリイミドフィルム[カプトン50H、東レ・デュポン(株)製]にスクリーン印刷により塗布し、150℃で30分熱硬化した。なお、硬化後のペースト膜厚は約15μmに調整した。
得られた各評価用サンプルついて、UL94規格に準拠した薄材垂直燃焼試験を行った。
各試験基板に、芯の先が平らになるように研がれたB〜9Hの鉛筆を、約45°の角度で押し付けて、硬化皮膜の剥がれが生じない鉛筆の硬さを記録した。
ロジン系フラックスを塗布した試験基板を、予め260℃に設定したはんだ槽に10秒間フローさせた。その後、プロピレングリコールモノメチルエーテルアセテートにより洗浄し、乾燥させた後、セロハン粘着テープによるピールテストを行い、硬化皮膜の剥がれについて評価した。判定基準は以下のとおりである。
○:硬化皮膜の剥がれが認められない。
△:硬化皮膜の剥がれが若干ある。
×:硬化皮膜の剥がれがある。
各熱硬化性樹脂組成物のペーストをそれぞれカプトン200H(東レ・デュポン(株)製ポリイミドフィルム、厚さ50μm)にスクリーン印刷で全面印刷し、150℃で60分間熱硬化させた。なお、硬化後のペースト膜厚は約15μmに調整した。その硬化皮膜の密着性を、JIS D 0202に従い、以下の基準で評価した。
○:硬化皮膜の剥がれが認められない。
△:硬化皮膜の剥がれが若干ある。
×:硬化皮膜の剥がれがある。
Claims (5)
- (A)熱分解開始温度が260℃未満のカルボキシル基含有樹脂、(B)熱分解開始温度が260℃以上のカルボキシル基含有樹脂、(C)難燃性化合物、(D)酸化チタン、及び(E)熱硬化性成分を含有する組成物であって、前記熱分解開始温度が260℃未満のカルボキシル基含有樹脂(A)と熱分解開始温度が260℃以上のカルボキシル基含有樹脂(B)の比率が質量基準で50〜80:50〜20の範囲にあることを特徴とする難燃性熱硬化性樹脂組成物。
- 前記熱分解開始温度が260℃未満のカルボキシル基含有樹脂(A)が芳香環を有しないことを特徴とする請求項1に記載の難燃性熱硬化性樹脂組成物。
- 前記熱分解開始温度が260℃以上のカルボキシル基含有樹脂(B)が芳香環を有することを特徴とする請求項1又は2に記載の難燃性熱硬化性樹脂組成物。
- 請求項1乃至3のいずれか1項に記載の難燃性熱硬化性樹脂組成物を基材上に塗布し、硬化させて得られる硬化物。
- 請求項1乃至3のいずれか1項に記載の難燃性熱硬化性樹脂組成物の硬化物からなる絶縁層又は保護膜を有するプリント配線板。
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JP2015147909A (ja) * | 2014-02-07 | 2015-08-20 | 太陽インキ製造株式会社 | 硬化性樹脂組成物、その硬化皮膜、およびこれを備えた加飾ガラス板 |
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JP2017504689A (ja) * | 2013-12-20 | 2017-02-09 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 難燃の熱可塑性ポリウレタン |
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