JP2019183048A - 光熱併用硬化型樹脂組成物、接着剤及びその硬化物 - Google Patents
光熱併用硬化型樹脂組成物、接着剤及びその硬化物 Download PDFInfo
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- JP2019183048A JP2019183048A JP2018077448A JP2018077448A JP2019183048A JP 2019183048 A JP2019183048 A JP 2019183048A JP 2018077448 A JP2018077448 A JP 2018077448A JP 2018077448 A JP2018077448 A JP 2018077448A JP 2019183048 A JP2019183048 A JP 2019183048A
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Abstract
Description
カチオン重合型の接着剤の硬化速度にはカチオン重合開始剤の構造が影響することが知られている。例えば特許文献1乃至9には、ヨードニウム塩やスルホニウム塩等のオニウム塩を有するカチオン重合開始剤(酸発生剤)の硬化性能や架橋反応性能はアニオンの種類に依存し、BF4 −塩<PF6 −塩<AsF6 −塩<SbF6 −塩の順に良くなることが記載されている。しかしながら、重合や架橋性能の良いAsF6 −やSbF6 −を含有するカチオン重合開始剤は、AsやSbの毒性の問題からSbF6 −塩が光造形などの限定された用途で使用されているのみである。安全性の観点からは一般的には重合や架橋性能の劣るPF6 −塩が利用されるが、例えばPF6 −塩を用いてSbF6 −塩と同程度の硬化速度を得るにはSbF6 −塩の10倍近い量を用いる必要があり、カチオン重合開始剤を溶解するために必要に応じて使用される溶剤量や硬化物中に残存する開始剤の分解物の量が多くなるために硬化物の物性が損なわれることが問題であった。
(1)(A)酸発生剤と(B)オキセタン化合物を含む組成物であって、該(A)酸発生剤が下記式(1)
(2)R1乃至R4がそれぞれ独立にパーフルオロアルキル基を置換基として有するフェニル基又はフッ素原子を置換基として有するフェニル基である前項(1)に記載の組成物、
(3)R1乃至R4がそれぞれ独立にペンタフルオロフェニル基又はビス(トリフルオロメチル)フェニル基である前項(2)に記載の組成物、
(4)(A)酸発生剤が、式(1)で表されるアニオンと硫黄原子、ヨウ素原子、窒素原子又はリン原子を有するカチオンからなる塩を含有する前項(1)に記載の組成物、
(5)(B)オキセタン化合物のオキセタン当量が、150乃至600g/eq.である前項(1)に記載の組成物、
(6)更にエポキシ化合物を含む前項(1)に記載の組成物、
(7)エポキシ化合物のエポキシ当量が、130乃至1000g/eq.である前項(6)に記載の組成物、
(8)エポキシ化合物の含有量が、オキセタン化合物100質量部に対して5乃至95質量部である前項(6)に記載の組成物、
(9)前項(1)乃至(8)のいずれか一項に記載の組成物を含む電子部品用接着剤、及び
(10)前項(1)乃至(8)のいずれか一項に記載の組成物の硬化物、
に関する。
本発明の組成物に含まれる(A)酸発生剤は前記式(1)で表されるアニオンとカチオンからなる塩を含有する。
式(1)中、R1乃至R4はそれぞれ独立に炭素数1乃至18のアルキル基又は炭素数6乃至14のアリール基を表すが、R1乃至R4の少なくとも一つは炭素数6乃至14のアリール基を表す。即ち、式(1)におけるR1乃至R4は以下いずれかの組合せである。
(i)R1乃至R4のうちの一つがアリール基で残りの三つがアルキル基の組合せ。
(ii)R1乃至R4のうちの二つがアリール基で残りの二つがアルキル基の組合せ。
(iii)R1乃至R4のうちの三つがアリール基で残りの一つがアルキル基の組合せ。
(iv)R1乃至R4の全てがアリール基の組合せ。
上記の組合せのうち、(iii)又は(iv)のアニオンが好ましく、(iv)のアニオンがより好ましい。
式(1)のR1乃至R4が表す炭素数1乃至18のアルキル基は置換基を有していてもよい。ここで言う「置換基を有するアルキル基」とは、アルキル基がその構造中に有する水素原子が置換基で置換されたアルキル基を意味し、置換基の位置及び置換基の数は特に限定されない。尚、置換基が炭素原子を有する場合、R1乃至R4が表すアルキル基の炭素数には置換基が有する炭素原子の数は含まれない。具体的には、例えばフェニル基を置換基として有するエチル基の場合、炭素数2のアルキル基となる。
式(1)のR1乃至R4が表す炭素数1乃至18のアルキル基が置換基として有していてもよいアルコキシ基とは、酸素原子とアルキル基が結合した置換基であり、アルコキシ基が有するアルキル基としては、例えば式(1)のR1乃至R4が表す炭素数1乃至18のアルキル基の項に記載したアルキル基と同じものが挙げられる。
式(1)のR1乃至R4が表す炭素数1乃至18のアルキル基が置換基として有していてもよい芳香族基とは、芳香族化合物の芳香環から水素原子を一つ除いた残基であれば特に限定されず、例えばフェニル基、ビフェニル基、ターフェニル基、クオーターフェニル基、トリル基、インデニル基、ナフチル基、アントリル基、フルオレニル基、ピレニル基、フェナンスニル基及びメスチル基等が挙げられる。
式(1)のR1乃至R4が表す炭素数1乃至18のアルキル基が置換基として有していてもよいアルキル置換アミノ基は、モノアルキル置換アミノ基及びジアルキル置換アミノ基の何れにも制限されず、これらアルキル置換アミノ基におけるアルキル基としては、例えば式(1)のR1乃至R4が表す炭素数1乃至18のアルキル基の項に記載したアルキル基と同じものが挙げられる。
式(1)のR1乃至R4が表す炭素数1乃至18のアルキル基が置換基として有していてもよいアリール置換アミノ基は、モノアリール置換アミノ基及びジアリール置換アミノ基の何れにも制限されず、これらアリール置換アミノ基におけるアリール基としては、式(1)のR1乃至R4が表す炭素数1乃至18のアルキル基が置換基として有していてもよい芳香族基と同じものが挙げられる。
式(1)のR1乃至R4が表す炭素数6乃至14のアリール基は置換基を有していてもよい。ここで言う「置換基を有するアリール基」とは、アリール基がその構造中に有する水素原子が置換基で置換されたアリール基を意味し、置換基の位置及び置換基の数は特に限定されない。尚、置換基が炭素原子を有する場合、R1乃至R4が表すアリール基の炭素数には置換基が有する炭素原子の数は含まれない。具体的には、例えばエチル基を置換基として有するフェニル基の場合、炭素数6のアリール基となる。
式(1)のR1乃至R4が表す炭素数6乃至14のアリール基が置換基として有していてもよいアルキル基としては、例えば式(1)のR1乃至R4が表す炭素数1乃至18のアルキル基の項に記載したアルキル基と同じものが挙げられる。
式(1)のR1乃至R4が表す炭素数6乃至14のアリール基が置換基として有していてもよいアルコキシ基、芳香族基、複素環基、ハロゲン原子、アルキル置換アミノ基及びアリール置換アミノ基の具体例としては、式(1)のR1乃至R4が表す炭素数1乃至18のアルキル基が置換基として有していてもよいアルコキシ基、芳香族基、複素環基、ハロゲン原子、アルキル置換アミノ基及びアリール置換アミノ基と同じものが挙げられる。
また、(A)酸発生剤中の式(1)で表されるアニオンとカチオンからなる塩の含有量は、本発明の効果が損なわれない限り特に限定されるものではないが、好ましくは80質量%以上、より好ましくは90質量%以上、更に好ましくは95質量%以上である。
尚、本発明におけるオキセタン当量とは、化合物中のオキセタン基1当量当たりの分子量のことであり、JISK7236:2001(ISO3001:1999に対応)に準じて測定した値を意味する。
本発明の組成物に(B)オキセタン化合物以外のカチオン重合性化合物を併用する場合の(B)オキセタン化合物以外のカチオン重合性化合物の含有量は、(B)オキセタン化合物100質量部に対して通常99質量部以下、好ましくは5乃至95質量部、より好ましくは20乃至95質量部である。
尚、本発明におけるエポキシ当量とは、化合物中のエポキシ基1当量当たりの分子量のことであり、JISK7236:2001(ISO3001:1999に対応)に準じて測定した値を意味する。
基材上に設けられた本発明の組成物からなる接着剤にエネルギー光を照射した後、該組成物層上に基材を設置し、次いで加熱することにより基材同士の接着体を得ることが出来る。貼り合わせる際は適当な圧力をかけてもよく、加温しながら貼り合わせてもよい。
照射に用いるエネルギー光は、(A)酸発生剤の吸収波長の光を発するものであれば特に限定されず、可視光線、紫外線、X線又は電子線等の活性エネルギー線を使用することができるが、紫外線が好ましい。
加熱温度及び加熱時間は、組成物が熱硬化し、基材同士が接着する温度及び時間であれば特に限定されないが、好ましくは80℃以上で30分間以上である。加熱温度及び加熱時間は、基材の耐熱温度を考慮して選択することが好ましい。
エネルギー線は、エネルギー線の積算光量が100乃至500mJ/cm2となる量を照射することが好ましい。 エネルギー線の積算光量が大き過ぎると貼りあわせ前に組成物がタックフリーとなって貼り合せ時に基材の表面にうまく密着せず、熱硬化後の接着強度が低くなってしまう可能性がある。
表1に記載した量(単位は質量部)のA−1及びA−2成分を100℃で10分間撹拌混合した後、B−1乃至B−3成分を加えて撹拌溶解した。放冷後、孔径50μmのメンブランフィルターによって濾過を施し、本発明及び比較用の樹脂組成物を得た。
実施例1及び比較例1乃至3で得られた各組成物を、バーコーターを用いて厚さが50μmとなるようポリフェニレンエーテル基材上に塗工した。次いで、メタルハライドランプを用いて、180mJ/365nmのエネルギーを照射後、100℃の熱風式乾燥機で1時間硬化を行った。アセトンを浸みこませた綿棒で得られた硬化膜の表面を往復10回こすり、以下の基準で硬化性を評価した。結果を表1に示した。
・評価の基準
○:外観変化なし
×:艶が消失や膜の溶解等の外観変化有り
上記「組成物の硬化性の評価」の手法に準じて得られた硬化膜をポリフェニレンエーテル基材より剥がして約0.2部を精秤して試験片とした。前記で得られた試験片とイオン交換蒸留水10部を入れたテフロン(登録商標)製のPCT容器をSUS製の圧力容器で密閉し、121℃、2気圧の条件下に20時間放置した後、室温まで放冷してから抽出水を取り出して導電率を測定し、以下の基準で電気伝導度を評価した。結果を表1に示した。
・評価基準
導電率が50μS/cm未満;〇
導電率が50μS/cm以上100μS/cm未満;△
導電率が100μS/cm以上;×
(A−1):商品名 RE−303S−L(ビスフェノールF型エポキシ樹脂、エポキシ当量167g/eq.、日本化薬株式会社製)
(A−2):商品名 アロンオキセタン OXT−121(キシリレンビスオキセタン、東亜合成株式会社製)
(B−1):商品名 CPI−310FG(アリールスルホニウムーテトラキスペンタフルオロガレイト、サンアプロ株式会社製)
(B−2):商品名 CPI−210S(4−(フェニルチオ)フェニルジフェニルスルホニウムトリス(ペンタフルオロエチル)トリフルオロホスフェート、サンアプロ株式会社製)
(B−3):商品名 Irgacure 290(トリス[4−(4−アセチルフェニル)スルホニルフェニル]スルホニウムテトラキス(2,3,4,5,6−ペンタフルオロフェニル)ボレート、BASF社製)
Claims (10)
- R1乃至R4がそれぞれ独立にパーフルオロアルキル基を置換基として有するフェニル基又はフッ素原子を置換基として有するフェニル基である請求項1に記載の組成物。
- R1乃至R4がそれぞれ独立にペンタフルオロフェニル基又はビス(トリフルオロメチル)フェニル基である請求項2に記載の組成物。
- (A)酸発生剤が、式(1)で表されるアニオンと硫黄原子、ヨウ素原子、窒素原子又はリン原子を有するカチオンからなる塩を含有する請求項1に記載の組成物。
- (B)オキセタン化合物のオキセタン当量が、150乃至600g/eq.である請求項1に記載の組成物。
- 更にエポキシ化合物を含む請求項1に記載の組成物。
- エポキシ化合物のエポキシ当量が、130乃至1000g/eq.である請求項6に記載の組成物。
- エポキシ化合物の含有量が、オキセタン化合物100質量部に対して5乃至95質量部である請求項6に記載の組成物。
- 請求項1乃至8のいずれか一項に記載の組成物を含む電子部品用接着剤。
- 請求項1乃至8のいずれか一項に記載の組成物の硬化物。
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