JP5532293B2 - 硬化性樹脂組成物、その硬化物、及びプラスチックレンズ - Google Patents
硬化性樹脂組成物、その硬化物、及びプラスチックレンズ Download PDFInfo
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- JP5532293B2 JP5532293B2 JP2009252904A JP2009252904A JP5532293B2 JP 5532293 B2 JP5532293 B2 JP 5532293B2 JP 2009252904 A JP2009252904 A JP 2009252904A JP 2009252904 A JP2009252904 A JP 2009252904A JP 5532293 B2 JP5532293 B2 JP 5532293B2
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- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
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- 125000001424 substituent group Chemical group 0.000 description 7
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- 229910052736 halogen Inorganic materials 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
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- 229910052753 mercury Inorganic materials 0.000 description 5
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- 239000002904 solvent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
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- 239000002585 base Substances 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
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Description
で表される置換基を有する化合物(D4)も挙げられる。このようなビナフタレン骨格を有することから、耐熱性及び耐湿性が良好なものとなると共に、有機材料としては極めて高い1.60以上の屈折率を有する材料となる。また、該ビナフタレン骨格上の置換基として末端にアクリロイルオキシ基又はメタクロイルオキシ基を有するアルキルオキシ基又はポリオキシアルキレン基を有することから反応性官能基である(メタ)アクリロイルオキシ基の自由度が高くなり、反応性に優れ硬化物の耐熱性・耐湿性が高くなる。
で表される置換基は、本発明の(メタ)アクリレート樹脂を活性エネルギー線の照射、或いは加熱により硬化させる際の反応性基として機能する構造部位である。該構造部位は、モノアルキルオキシ基又はポリオキシアルキレン基を介して(メタ)アクリロイルオキシ基がビナフタレン構造に結合していることから、反応性官能基である(メタ)アクリロイルオキシ基の自由度が高くなり、反応性が優れると共に、硬化物の耐熱性・耐湿性が高くなる。
で表される分子構造を有するものが挙げられる。
2)13C−NMR:日本電子株式会社製NMR「GSX270」
3)FD−MS:日本電子株式会社製 二重収束型質量分析装置「AX505H(FD505H)」
攪拌機、温度計、ディーンスタークトラップ、コンデンサーが装着された5Lの4つ口フラスコにビナフトール858g(3モル)、エチレンカーボネート634g(7.2モル)、48質量%水酸化カリウム24gを加え、170℃で4時間反応させた。その後、メチルイソブトキシケトン1500gを加えて溶解し、水1000gを加え、攪拌を停止して下層を棄却した。更に水1000gを加え、攪拌を停止して下層を棄却した。その後、150℃で脱溶剤を行いDSC測定による融点108℃の樹脂1050gを得た。この樹脂をマススペクトル(FD−MS)で測定し、M=374のピークが確認されたこと、また、図1に示した13C−NMRの測定結果から、下記構造式で表される水酸基含有化合物(a)であることを確認した。
下記第1表の配合に従い、活性エネルギー線硬化型樹脂組成物を調製した。この組成物の粘度(25℃)の粘度を測定するとともに、組成物を40℃の恒温装置に1ヶ月間静置させた。1ヶ月後再び組成物の粘度を測定し、以下の基準によって評価した。
○:粘度の上昇率が101〜200%未満
△:粘度の上昇率が201〜300%未満
前記活性エネルギー線硬化型樹脂組成物をそれぞれ、アプリケーター(0.152mm)を用いてPETフィルム(A4300:東洋紡績製)に塗布し、PETフィルム上に塗膜層を作成した。PETフィルムに形成した塗膜層の上にクロムメッキ処理板を置くことで、塗膜層をPETフィルムとクロムメッキ処理板でラミネートした。次に80W/cm2の高圧水銀灯を用い、PETフィルム側から紫外線を照射し、以下の基準に従って硬化性を評価した。
△:活性エネルギー線の積算照射量が500mJ/cm2で硬化塗膜にタックがあったが活性エネルギー線の積算照射量が1000mJ/cm2でタックのない硬化塗膜が得られた。
×:活性エネルギー線の積算照射量が1000mJ/cm2でも硬化塗膜にタックがあった。
DVB−810:1,3−ジビニルベンゼン、1,4−ジビニルベンゼン及びエチルビニルベンゼンの混合物。DVB−810中の1,3−ジビニルベンゼンと1,4−ジビニルベンゼン含有率は81%。
イルガキュア819:ビス(2,4,6−トリメチルベンゾイル)−フェニルホスフィンオキサイド
ダロキュアTPO:2,4,6−トリメチルベンゾイルージフェニルーホスフィンオキサイド
アクリレート樹脂(D2):ビスフェノキシエタノールフルオレンジアクリレート
アクリレート樹脂(D3):エポキシアクリレート(DIC製「ユニディックV−5500」)
OPPEA:o−フェニルフェノールエチレンオキサイド変性アクリレート
PEA:フェノキシエチルアクリレート
イルガキュア184D:1−ヒドロキシーシクロヘキシルーフェニルーケトン
MEHQ:メトキノン
Qー1301:アルミニウムN−ニトロソフェニルヒドロキシアミン
Claims (12)
- ジビニルベンゼン系化合物、ジビニルナフタレン系化合物、ジビニルビフェニル系化合物及びこれらの誘導体からなる群から選ばれる1種以上の芳香環に重合性不飽和二重結合が直接結合している化合物(A)とホスフィンオキサイド系光重合開始剤(B)と無水マレイン酸(C)とを含有し、前記化合物(A)100質量部に対して無水マレイン酸(C)を0.1〜10質量部含有することを特徴とする活性エネルギー線硬化性樹脂組成物。
- 前記化合物(A)が1,3−ジビニルベンゼン、または1,4−ジビニルベンゼンである請求項1記載の活性エネルギー線硬化性樹脂組成物。
- 前記重合開始剤(B)フェニルビス(2,4,6−トリメチルベンゾイル)−ホスフェンオキシドである請求項1記載の活性エネルギー線硬化性樹脂組成物。
- 更に、(メタ)アクリロイル基を有する化合物(D)を含有する請求項1記載の活性エネルギー線硬化性樹脂組成物。
- 前記無水マレイン酸(C)の含有量が、化合物(A)と化合物(D)との合計100質量部に対して0.1〜10質量部である請求項4記載の活性エネルギー線硬化性樹脂組成物。
- 前記化合物(D)が、25℃での屈折率が1.58以上である化合物である請求項4記載の活性エネルギー線硬化性樹脂組成物。
- 更に重合禁止剤(E)を有する請求項1記載の活性エネルギー線硬化性樹脂組成物。
- 前記重合禁止剤(E)がアルミニウムN−ニトロソフェニルヒドロキシアミンである請求項9記載の活性エネルギー線硬化性樹脂組成物。
- 請求項1〜10のいずれか1項記載の活性エネルギー線硬化性樹脂組成物を硬化させてなることを特徴とする硬化物。
- 請求項1〜10のいずれか1項記載の活性エネルギー線硬化性樹脂組成物を成形、硬化させてなることを特徴とするプラスチックレンズ。
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