JP2016020472A - 光重合性樹脂組成物及びその硬化物並びに硬化物の製造方法 - Google Patents
光重合性樹脂組成物及びその硬化物並びに硬化物の製造方法 Download PDFInfo
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- JP2016020472A JP2016020472A JP2015026719A JP2015026719A JP2016020472A JP 2016020472 A JP2016020472 A JP 2016020472A JP 2015026719 A JP2015026719 A JP 2015026719A JP 2015026719 A JP2015026719 A JP 2015026719A JP 2016020472 A JP2016020472 A JP 2016020472A
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Abstract
【解決手段】光カチオン重合性化合物(A)とポリシラン(B)と可視光線を吸収して酸を発生する光酸発生剤(C)とを組み合わせて光重合性樹脂組成物を調製する。前記光酸発生剤(C)は複素環を含み、かつ波長405nmの可視光線を吸収して酸を発生する光酸発生剤、特に、イミド環と共役したチアントレン骨格を有する光酸発生剤であってもよい。前記光カチオン重合性化合物(A)はフルオレン骨格を有していてもよい。この組成物に可視光線を照射して光硬化物を形成する光硬化工程を含む製造方法により、屈折率が高く、透明性、耐熱性及び撥水性も優れた硬化物が得られる。この製造方法では、光硬化物を80〜150℃でさらに加熱してもよく、光硬化工程において、可視光線の照射とともに、80〜150℃で組成物を加熱してもよい。
【選択図】なし
Description
本発明の光重合性樹脂組成物は、光カチオン重合性化合物(A)、ポリシラン(B)及び可視光線を吸収して酸を発生する光酸発生剤(C)を含む。
光カチオン重合性化合物(A)は、光酸発生剤から発生した酸によりカチオン重合可能であればよく、通常、エポキシ樹脂(グリシジルエーテル型エポキシ樹脂、グリシジルエーテル型エポキシ樹脂、脂環式エポキシ樹脂、グリシジルアミン型エポキシ樹脂など)などを使用できる。光カチオン重合性化合物は、例えば、芳香族エポキシ樹脂(フェノールノボラック型エポキシ樹脂などのノボラック型エポキシ樹脂や、ビスフェノールA型エポキシ樹脂などのビスフェノール型エポキシ樹脂など)や、脂環族型エポキシ樹脂(水添ビスフェノールA型エポキシ樹脂などの水添ビスフェノール型エポキシ樹脂など)などのエポキシ樹脂であってもよいが、硬化物を高屈折率化できる点から、フルオレン骨格を有する光カチオン重合化合物が好ましく、前記式(2)で表されるエポキシ化合物[エポキシ化合物(2)]が好ましい。
ポリシラン(B)としては、Si−Si結合を有する直鎖状、環状、分岐鎖状、又は網目状の化合物であれば特に限定されないが、通常、下記式(3)及び(4)で表される構造単位のうち少なくとも1つの構造単位を有するポリシランで構成されている場合が多い。
光酸発生剤(C)は、可視光線を吸収して酸を発生できればよいが、可視光線の吸収性に優れ、酸発生能が高い点から、複素環(ヘテロ環)を含む光酸発生剤が好ましい。
本発明の光重合性樹脂組成物は、さらに慣用の他の添加剤を含んでいてもよい。他の添加剤としては、他の光酸発生剤(イミジルスルホネート化合物、チオキサントンオキシムエステル化合物、オニウム塩、メタロセン錯体、スルホンイミド化合物、ジスルホン化合物、スルホン酸エステル化合物、トリアジン化合物、キノンジアジド化合物、ジアゾメタン化合物など)、増感剤(クマリン類、キノリン類、キノン類、ピレン類、フェノキサジン類、芳香族炭化水素類、アミン類など)、反応性ポリマー(フェノール系樹脂などのエポキシ基に対する反応性基を有するポリマーなど)、着色剤(染顔料)、増粘剤、安定剤(老化防止剤、酸化防止剤、オゾン劣化防止剤など)、消泡剤、レベリング剤、分散剤、難燃剤、帯電防止剤、充填剤、滑剤などが挙げられる。これらの添加剤は、単独で又は二種以上組み合わせて使用できる。これらの添加剤の割合は、添加剤の種類に応じて適宜選択できるが、例えば、光カチオン重合性化合物(A)100重量部に対して、100重量部以下(例えば、0.1〜50重量部)、好ましくは0.3〜30重量部、さらに好ましくは0.5〜20重量部程度である。
本発明では、前記光重合性樹脂組成物に可視光線を照射して光硬化物を形成する光硬化工程を含む製造方法により硬化物(三次元的硬化物、硬化膜や硬化パターンなどの一次元又は二次元的硬化物、点又はドット状硬化物など)を製造してもよい。
(光カチオン重合性化合物)
BCAFG:9,9’−ビス[(3,4−ジグリシジルオキシ)フェニル]フルオレン、大阪ガスケミカル(株)製「BCAFG」
FBPEG:9,9’−ビス[(4−グリシジルオキシエトキシ)フェニル]フルオレン、大阪ガスケミカル(株)製「FBPEG」。
PMPS:ポリメチルフェニルシラン、大阪ガスケミカル(株)製「PMPS」、数平均分子量Mn=11000
hb−PPS:ハイパーブランチドフェニルシランオリゴマー、大阪ガスケミカル(株)製「hb−PPS」、数平均分子量Mn=600。
tBuTHITf:N−トリフルオロメタンスルホニルオキシ−7−t−ブチル−チアントレン−2,3−ジカルボン酸イミド、(株)三宝化学研究所製「tBuTHITf」
TPST:トリフェニルスルホニウム トリフルオロメタンスルホン酸塩、みどり化学(株)製「TPST」
NITf:N−トリフルオロメタンスルホニルオキシ−1,8−ナフタルイミド、みどり化学(株)製「NITf」。
実施例及び比較例で得られた硬化物を分光光度計((株)島津製作所「UV−2400PC」)を用いて測定した。
実施例及び比較例で得られた硬化物の厚みを測定した後、硬化物をTHF中に10分間浸漬した後、THF中から取り出し、浸漬後の厚みを測定し、浸漬前後の厚みを不溶化率として算出した。
多波長アッベ屈折計((株)アタゴ製「DR−M2」)を用い、温度25℃の条件で、F線、D線及びC線での屈折率nF、nD及びnC(各々波長486nm、589nm、656nmの干渉フィルター使用)を測定した。
実施例及び比較例で得られた硬化物について、熱重量分析装置(TG−DTA、(株)島津製作所製「DTG−60」)を用い、加熱前のペレット状樹脂組成物と比較して重量が5重量%及び50重量%減少した温度(℃)、熱分解が開始した温度及び熱分解が終了した温度(℃)を測定した。
光カチオン重合性化合物、ポリシラン及び光酸発生剤を、表1に示す組成及び割合(重量部)で、シクロヘキサノン1000重量部中に溶解し、光重合性樹脂組成物を調製した。得られた組成物を、シリコン板上にスピンコートし、膜厚0.12〜0.5μmのサンプルフィルムを調製した。
光カチオン重合性化合物、ポリシラン及び光酸発生剤を、表2に示す組成及び割合(重量部)で、シクロヘキサノン1000重量部中に溶解し、光重合性樹脂組成物を調製した。得られた組成物を、シリコン板上にスピンコートし、膜厚0.3〜0.5μmのサンプルフィルムを調製した。実施例3で得られたサンプルフィルムを実施例1と同様の方法で、可視光線で光照射した後、110℃で4分間加熱した。得られたサンプルフィルムの不溶化率を測定した結果を表2に示す。なお、表2には、実施例1及び2のサンプルフィルムについての結果と、実施例1〜3のサンプルフィルムについて、光照射を行わなかったフィルムの結果も参考例として示す。
光カチオン重合性化合物及び光酸発生剤を、表3に示す組成及び割合(重量部)で、シクロヘキサノン1000重量部中に溶解し、光重合性樹脂組成物を調製した。得られた組成物を、シリコン板上にスピンコートし、膜厚0.3〜0.5μmのサンプルフィルムを調製した。比較例3で得られたサンプルフィルムを実施例1と同様の方法で、可視光線で光照射した後、110℃で4分間加熱した。得られたサンプルフィルムと、実施例3で得られたサンプルフィルムについて、光学特性を測定した結果を表3に示す。
Claims (12)
- 光カチオン重合性化合物(A)、ポリシラン(B)及び可視光線を吸収して酸を発生する光酸発生剤(C)を含む光重合性樹脂組成物。
- 光酸発生剤(C)が、複素環を含み、かつ波長405nmの可視光線を吸収して酸を発生する請求項1記載の光重合性樹脂組成物。
- 光酸発生剤(C)が、イミド環と共役したチアントレン骨格を有する請求項1又は2記載の光重合性樹脂組成物。
- 光カチオン重合性化合物(A)がフルオレン骨格を有する光カチオン重合性化合物である請求項1〜4のいずれかに記載の光重合性樹脂組成物。
- 光カチオン重合性化合物(A)が、下記式(2)で表されるエポキシ化合物である請求項1〜5のいずれかに記載の光重合性樹脂組成物。
- 式(2)において、nが2である請求項6記載の光重合性樹脂組成物。
- ポリシラン(B)が、数平均分子量100〜50000のポリC1−3アルキルC6−10アリールシランである請求項1〜7のいずれかに記載の光重合性樹脂組成物。
- 請求項1〜8のいずれかに記載の組成物に可視光線を照射して光硬化物を形成する光硬化工程を含む硬化物の製造方法。
- 光硬化物を80〜150℃で加熱する加熱工程を含む請求項9記載の製造方法。
- 光硬化工程において、可視光線を照射し、80〜150℃で組成物を加熱する請求項9記載の製造方法。
- 請求項9〜11のいずれかに記載の製造方法で得られた硬化物。
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