JP2011068755A - 光硬化性組成物 - Google Patents
光硬化性組成物 Download PDFInfo
- Publication number
- JP2011068755A JP2011068755A JP2009220413A JP2009220413A JP2011068755A JP 2011068755 A JP2011068755 A JP 2011068755A JP 2009220413 A JP2009220413 A JP 2009220413A JP 2009220413 A JP2009220413 A JP 2009220413A JP 2011068755 A JP2011068755 A JP 2011068755A
- Authority
- JP
- Japan
- Prior art keywords
- photopolymerization initiator
- photoacid generator
- photosensitive wavelength
- carbon atoms
- oxime ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 oxime ester Chemical class 0.000 claims abstract description 47
- 239000003999 initiator Substances 0.000 claims abstract description 43
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 239000011248 coating agent Substances 0.000 claims description 16
- 238000000576 coating method Methods 0.000 claims description 16
- 239000000758 substrate Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 10
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- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims 1
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- WZESLRDFSNLECD-UHFFFAOYSA-N phenyl prop-2-eneperoxoate Chemical compound C=CC(=O)OOC1=CC=CC=C1 WZESLRDFSNLECD-UHFFFAOYSA-N 0.000 description 1
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- 238000010992 reflux Methods 0.000 description 1
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Landscapes
- Macromonomer-Based Addition Polymer (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Polymerisation Methods In General (AREA)
Abstract
Description
このようにして硬化物において、コントラストの高い画像が形成されるとともに、優れた画像安定性及び良好な硬化物性を得ることができる。
本実施形態の光硬化性組成物における光酸発生剤は、電子供与性染料に対し、顕色効果を示す電子受容性化合物であり、電子活性エネルギー線の照射により酸を発生し、後述する電子供与性染料を発色させるために用いられる。
これらの光酸発生剤は、単独で、又は2種類以上組み合わせて用いることができる。
このようなオキシムエステル系光重合開始剤としては、可視光源で汎用されている405nmに良好な感度を有することから、下記式(II)で表される2−(アセチルオキシイミノメチル)チオキサンテン−9−オンが好ましい。
このようなオキシムエステル系光重合開始剤は、単独で、又は2種類以上組み合わせて用いることができる。
これらエチレン性不飽和基含有化合物は、1種又は2種以上任意に組み合わせることができる。
このような本実施形態の光硬化性組成物を用いて、例えば以下のようにして所定のパターンを有する画像を形成することができる。ただし、本発明の光硬化性組成物を用いた画像形成方法は、コントラストの高い画像を形成でき、優れた画像安定性と良好な硬化物性を実現できるものであれば、以下の方法に限定されるものではなく、例えば、以下に説明する「第一露光工程」と「第二露光工程」を逆にすることもできる。
攪拌機、温度計、還流冷却管、滴下ロート及び窒素導入管を備えた2リットルのセパラブルフラスコに、クレゾールノボラック型エポキシ樹脂のエピクロンN−680(DIC社製、エポキシ当量=215g/当量)107.5部を入れ、カルビトールアセテート108部、出光石油化学製のイプゾール(登録商標)#150 108部を加え、加熱溶解し、樹脂溶液を得た。
*1:ネオマー(登録商標)DA-600(三洋化成工業社製)
*2:BYK(登録商標)-361N(ビックケミー・ジャパン社製)
*3:KS-66(信越シリコーン社製)
*4:CGI 325(チバ・スペシャルティ・ケミカルズ社製)
*5:IRGACURE(登録商標) OXE-02(チバ・スペシャルティ・ケミカルズ社製)
*6:IRGACURE OXE-01(チバ・スペシャルティ・ケミカルズ社製)
*7:IRGACURE 907(チバ・スペシャルティ・ケミカルズ社製)
*8:アデカ(登録商標)オプトマー SP-152(ADEKA社製)
*9:S-205(山田化学工業社製)
表1に示す組成物例1〜4の光硬化性組成物を、それぞれ銅ベタ基板をバフ研磨した後、スクリーン印刷法にて全面印刷し、80℃×30分乾燥することで、基板上に無色透明の塗膜を形成し、実施例1〜3、比較例4〜8の試験基板を得た。
第一露光工程:
ネガマスク越しにメタルハライドランプを用い、全光波長領域で1000J/cm2で光照射を行った。その後、80℃で10分間PEB処理を行った。
第二露光工程:
第一露光工程を経た試験基板に対して、光酸発生剤の感光波長域外で、オキシムエステル系光重合開始剤の感光波長域である405nmの波長を発振する直描露光機(PENTAX社製DI−μ)を用い、試験基板上の塗膜全体を 300J/cm2で光照射を行った。
実施例1〜3、比較例1〜5の試験基板について、塗膜の発色を目視で確認した。評価基準は以下の通りである。
発色あり・・・露光後の発色が見られる
発色なし・・・露光前後に色彩変化なし
実施例1〜4及び比較例1〜5の試験基板について、露光前、第一露光処理後及び第二露光処理後のタック性により、塗膜の硬化状態を評価した。評価基準は以下の通りである。
○・・・指蝕時に塗膜表面に指跡が全く残らない
×・・・指蝕時に塗膜表面に指跡が残る
実施例1〜3及び比較例1〜5の試験基板について、露光処理後の塗膜(硬化物)の硬化性を確認するため、着色部・未着色部において、それぞれプロピレングリコールモノメチルエーテルアセテート(PMA)を用いてラビングテストを10回行い、塗膜の溶解・剥がれを目視で確認した。評価基準は以下の通りである。
○・・・PMAラビング後、塗膜の溶解・剥がれなし
△・・・PMAラビング後、塗膜表面に濁り部あり
×・・・PMAラビング後、塗膜の溶解・剥がれあり
実施例1〜4及び比較例1〜4の試験基板について、露光処理後の塗膜(硬化物)について、蛍光灯下で1週間放置し、目視評価でカブリを確認した。評価基準は以下の通りである。
○・・・一週間放置しても、未着色部のカブリは見られず、コントラストが維持された状態
×・・・一週間放置すると、未着色部のカブリが見られ、コントラストが維持できない状態
Claims (3)
- 基板上に、請求項1又は請求項2に記載の光硬化性組成物の塗布膜を形成し、
前記光酸発生剤の感光波長域の少なくとも一部を含む第1の活性エネルギー線を所定パターンに照射し、酸を発生させ、前記電子供与性染料を発色させて着色部を形成した後、
前記光酸発生剤の感光波長域外で、かつ前記オキシムエステル系光重合開始剤の感光波長域の第2の活性エネルギー線を全面に照射して、前記オキシムエステル系光重合開始剤よりラジカルを発生させ、前記エチレン性不飽和基含有化合物を重合させて得られることを特徴とする硬化物。
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JP2015131927A (ja) * | 2014-01-15 | 2015-07-23 | 山本化成株式会社 | インクジェット光造形用液状樹脂組成物 |
CN105278242A (zh) * | 2014-07-15 | 2016-01-27 | 东京应化工业株式会社 | 感光性组合物 |
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