JP2010270230A - 重合性官能基及び紫外線吸収性基を有するシルセスキオキサン化合物 - Google Patents
重合性官能基及び紫外線吸収性基を有するシルセスキオキサン化合物 Download PDFInfo
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- JP2010270230A JP2010270230A JP2009123649A JP2009123649A JP2010270230A JP 2010270230 A JP2010270230 A JP 2010270230A JP 2009123649 A JP2009123649 A JP 2009123649A JP 2009123649 A JP2009123649 A JP 2009123649A JP 2010270230 A JP2010270230 A JP 2010270230A
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- carbon atoms
- silsesquioxane compound
- meth
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- 125000000524 functional group Chemical group 0.000 title abstract description 5
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- 238000004519 manufacturing process Methods 0.000 claims abstract description 28
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 107
- -1 acryloyloxy group Chemical group 0.000 claims description 88
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 38
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- 125000005843 halogen group Chemical group 0.000 claims description 26
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- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 229910000077 silane Inorganic materials 0.000 claims description 18
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 15
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
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- 239000011259 mixed solution Substances 0.000 description 5
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
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- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
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- 239000007983 Tris buffer Substances 0.000 description 3
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- 125000001309 chloro group Chemical group Cl* 0.000 description 3
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- 150000002170 ethers Chemical class 0.000 description 3
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
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- DPNXHTDWGGVXID-UHFFFAOYSA-N 2-isocyanatoethyl prop-2-enoate Chemical compound C=CC(=O)OCCN=C=O DPNXHTDWGGVXID-UHFFFAOYSA-N 0.000 description 2
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Abstract
Description
(ii)前記工程(i)で製造したシルセスキオキサン化合物の1級アミノ基と、下記一般式(V)
(iii)前記工程(ii)で製造した反応生成物と、下記一般式(VI)
を有する、
ケイ素原子に直接に結合した有機基を有するシルセスキオキサン化合物であって前記ケイ素原子に直接に結合した有機基の少なくとも1つが下記一般式(I)
本発明のシルセスキオキサン化合物は、ケイ素原子に直接に結合した有機基を有するシルセスキオキサン化合物であって、前記ケイ素原子に直接に結合した有機基の少なくとも1つが下記一般式(I)で表される有機基であることを特徴とするシルセスキオキサン化合物(以下、単に「本発明のシルセスキオキサン化合物」と略すことがある。)である。
本発明のシルセスキオキサン化合物の製造方法は、特に限定されるものではない。本発明のシルセスキオキサン化合物は、一般的なシルセスキオキサンの製造に用いられている製造方法と従来公知の化学反応とを組み合わせることにより得ることができる。なかでも好ましい製造方法を以下に説明する。
(ii)前記工程(i)で製造したシルセスキオキサン化合物の1級アミノ基と、下記一般式(V)
(iii)前記工程(ii)で製造した反応生成物と、下記一般式(VI)
を有する、ケイ素原子に直接に結合した有機基を有するシルセスキオキサン化合物であって前記ケイ素原子に直接に結合した有機基の少なくとも1つが下記一般式(I)
本発明の製造方法の工程(i)は、下記一般式(IV)
本発明の製造方法の工程(ii)は、前記工程(i)で製造したシルセスキオキサン化合物の1級アミノ基と、下記一般式(V)
本発明の製造方法の工程(iii)は、前記工程(ii)で製造した反応生成物と、下記一般式(VI)
本発明の活性エネルギー線硬化性組成物は、本発明のシルセスキオキサン化合物、及び光重合開始剤を含有する。
光重合開始剤としては、活性エネルギー線を吸収してラジカルを発生する開始剤であれば特に限定されることなく使用できる。
また本発明の活性エネルギー線硬化性組成物は、本発明のシルセスキオキサン化合物以外の重合性不飽和化合物を含有していてもよい。該重合性不飽和化合物としては、本発明のシルセスキオキサン化合物以外の化合物であって、その化学構造中に重合性不飽和二重結合を少なくとも1つ有する化合物であれば特に限定されない。
装置:JEOL社製 FT−NMR EX−400
溶媒:CDCl3
内部標準物質:テトラメチルシラン
還流冷却器、温度計、空気導入管、攪拌機を取り付けたセパラブルフラスコに、N−(2−アミノエチル)−3−アミノプロピルトリメトキシシラン580部、2−プロピルアルコール2,300部、テトラブチルアンモニウムフルオリド2部、及び脱イオン水70部を仕込み、60℃で8時間反応させた。減圧蒸留にて不揮発分60%となるまで濃縮した後、プロピレングリコールモノメチルエーテル1,000部を配合してさらに減圧蒸留を継続し、生成物(P1)の不揮発分40%溶液1,000部を得た。
還流冷却器、温度計、空気導入管、攪拌機を取り付けたセパラブルフラスコに、3−アミノプロピルトリメトキシシラン650部、2−プロピルアルコール2,600部、テトラブチルアンモニウムフルオリド2部、及び脱イオン水100部を仕込み、60℃で8時間反応させた。減圧蒸留にて不揮発分60%となるまで濃縮した後、プロピレングリコールモノメチルエーテル1,000部を配合してさらに減圧蒸留を継続し、生成物(P2)の不揮発分40%溶液1,000部を得た。
還流冷却器、温度計、空気導入管、攪拌機を取り付けたセパラブルフラスコに、生成物(P1)の不揮発分40%溶液100部、RUVA93{商品名、大塚化学社製、2−[2−ヒドロキシ−5−(2−メタクリロイルオキシエチル)フェニル−2H−1,2,3−ベンゾトリアゾール]}42部、プロピレングリコールモノメチルエーテル63部、及びメトキノン0.1部を配合し、空気を吹き込みながら常温で1時間攪拌した。110℃まで昇温し、この温度で8時間反応させ、生成物(P3)の不揮発分40%溶液205部を得た。
還流冷却器、温度計、空気導入管、攪拌機を取り付けたセパラブルフラスコに、生成物(P2)の不揮発分40%溶液100部、RUVA93{商品名、大塚化学製、2−[2−ヒドロキシ−5−(2−メタクリロイルオキシエチル)フェニル−2H−1,2,3−ベンゾトリアゾール]}82部、プロピレングリコールモノメチルエーテル123部、及びメトキノン0.1部を配合し、空気を吹き込みながら常温で1時間攪拌した。100℃まで昇温し、この温度で24時間反応させ、生成物(P5)の不揮発分40%溶液305部を得た。
還流冷却器、温度計、空気導入管、攪拌機を取り付けたセパラブルフラスコに、2−ヒドロキシエチルアクリレート52部、イソホロンジイシアネート100部、酢酸イソブチル38部、及びメトキノン0.1部を配合し、空気を液中に吹き込みながら80℃で12時間反応させ、生成物(P7)の不揮発分80%溶液190部を得た。生成物(P7)のNCO価は124mgNCO/gであった。
還流冷却器、温度計、窒素導入管、攪拌機を取り付けたセパラブルフラスコに、生成物(P7)の不揮発分80%溶液 50部、及びアセトン50部を配合し、窒素気流下で攪拌しながら氷浴で5℃まで冷却した。該セパラブルフラスコに生成物(P5)の不揮発分40%溶液100部を、滴下ロートにて反応溶液の温度が7℃を超えないように滴下した。減圧蒸留にてアセトンを除去した後、プロピレングリコールモノメチルエーテル50部を配合し、生成物(P9)の不揮発分40%溶液200部を得た。
還流冷却器、温度計、空気導入管、攪拌機を取り付けたセパラブルフラスコに、アセトン2,200部、脱イオン水120部、及びテトラブチルアンモニウムフルオリド3部を配合し、攪拌しながら溶解させた。ここに3−メタクリロイルオキシプロピルトリメトキシシラン554部を投入し、40℃にて12時間反応させた。プロピレングリコールモノメチルエーテルアセテート1,500部で希釈し、減圧蒸留にて揮発分を除去し、生成物(P10)の不揮発分40%溶液を得た。
生成物(P4)の不揮発分40%溶液と下記の重合性不飽和化合物(A1)を、生成物(P4)と重合性不飽和化合物(A1)の質量比が1:1になるように混合し、40℃で24時間攪拌して、混合溶液を得た。該混合溶液の相溶性を評価することにより、実施例1で得られた生成物(P4)と重合性不飽和化合物との溶液状態における相溶性を評価した。評価は、目視にて相溶状態を観察し、下記の基準に従って行った。評価結果を表1に示した。
○:均一、透明であり、相溶性は良好。
△:わずかに濁りがある、又は振った時に揺らぎが見え、相溶性は良好ではない。
×:かなり濁っている、又は分離、凝集、沈降物、ゲル化のいずれか1つ以上が見られ、相溶性は悪い。
A1:HDDA(商品名、ダイセルサイテック社製、1,6−ヘキサンジオールジアクリレート)
A2:アロニックスM−140(商品名、東亜合成社製、N-アクリロイルオキシエチルヘキサヒドロフタルイミド)
A3:アロニックスM−325[商品名、東亜合成社製、ε-カプロラクトン変性トリス(アクリロキシエチル)イソシアヌレート]
A4:トリメチロールプロパンジアクリレート
A5:ペンタエリスリトールジアクリレート
A6:ペンタエリスリトールトリアクリレート
A7:アロニックスM−403(商品名、東亜合成社製、ジペンタエリスリトールペンタ及びヘキサアクリレート)
A8:アロニックスM−1200(商品名、東亞合成社製、ニ官能ウレタンアクリレートオリゴマー)
実施例5と同様にして、実施例2〜4、比較例1で得られた各生成物(P6、P8、P9、P10)について、重合性不飽和化合物との溶液状態における相溶性を評価した。評価結果を表1に示した。
本発明のシルセスキオキサン化合物を含む活性エネルギー線硬化性組成物について、重合性不飽和化合物を混合した場合の相溶性を評価した。試験方法を以下に示す。
○:均一、透明であり、相溶性は良好。
△:わずかに濁りがあり、相溶性は良好ではない。
×:かなりに濁っている、又は凝集物、ブツ、はじきのいずれか1つ以上が見られ、相溶性は悪い。
生成物(P4)の不揮発分40%溶液を、実施例2〜4、比較例1で得られた生成物(P6、P8、P9、P10)の溶液の各々に替えた以外は、実施例9と同様にして、活性エネルギー線硬化性組成物を作成した。次いで、実施例9と同様の条件で該活性エネルギー線硬化性組成物を硬化させた塗膜を作成し、重合性不飽和化合物を混合した場合の相溶性を評価した。評価結果を表2に示した。
実施例9における活性エネルギー線硬化性組成物の作成方法、硬化塗膜の作成方法と同様にして、表3に示す配合の活性エネルギー線硬化性組成物を作成して、イソプロパノールにて脱脂したABS基板上に乾燥膜厚10μmの硬化塗膜を形成し、試験板を得た。得られた各試験板について、液安定性、耐擦傷性、耐候性を評価した。評価結果を表3に示した。
作成した活性エネルギー硬化性組成物を5℃の恒温室内にて1週間保管し、液状態を目視で観察し、下記の基準に従って評価した。
○:濁り、沈殿物等がなく、異常なし。
△:わずかな濁りが認められる。
×:明確な濁りや沈殿物が認められる。
各塗膜に市販のスチールウール(#0000)をこすりつけ、塗膜を目視で観察し下記の基準に従って評価した。
○:傷、ワレ、剥がれがない、若しくは傷が僅かにあるが実用上問題が無い。
△:傷が認められる。
×:ワレ、剥がれ、著しい傷等が認められる。
得られた各試験板ついてサンシャインウェザーオメーターを用いて、1000時間試験を行った後に、塗膜を目視で観察し下記の基準に従って評価した。
○:異常無し、若しくはフクレ、変色、ツヤ変化、剥がれ等が僅かに認められるが実用上問題が無い。
△:フクレ、変色、ツヤ変化、剥がれ等が認められる。
×:フクレ、変色、ツヤ変化、剥がれ等が著しく認められる。
Claims (7)
- ケイ素原子に直接に結合した有機基を有するシルセスキオキサン化合物であって、前記ケイ素原子に直接に結合した有機基の少なくとも1つが下記一般式(I)で表される有機基であることを特徴とするシルセスキオキサン化合物。
- 前記一般式(I)で表される有機基のR5がエチレン基であり、R6、R7、R8が各々水素原子であり、R9が水素原子である請求項1記載のシルセスキオキサン化合物。
- 重量平均分子量が1,000〜100,000である請求項1〜3のいずれか1項に記載のシルセスキオキサン化合物。
- 請求項1〜4のいずれか1項に記載のシルセスキオキサン化合物、及び光重合開始剤を含有する活性エネルギー線硬化性組成物。
- 前記シルセスキオキサン化合物以外の重合性不飽和化合物をさらに含有する請求項5記載の活性エネルギー線硬化性組成物。
- (i)下記一般式(IV)
(ii)前記工程(i)で製造したシルセスキオキサン化合物の1級アミノ基と、下記一般式(V)
(iii)前記工程(ii)で製造した反応生成物と、下記一般式(VI)
を有する、
ケイ素原子に直接に結合した有機基を有するシルセスキオキサン化合物であって前記ケイ素原子に直接に結合した有機基の少なくとも1つが下記一般式(I)
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