JP2012072232A - 重合性フッ素系化合物、それを用いた活性エネルギー線硬化型組成物及びその硬化物 - Google Patents
重合性フッ素系化合物、それを用いた活性エネルギー線硬化型組成物及びその硬化物 Download PDFInfo
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- JP2012072232A JP2012072232A JP2010216957A JP2010216957A JP2012072232A JP 2012072232 A JP2012072232 A JP 2012072232A JP 2010216957 A JP2010216957 A JP 2010216957A JP 2010216957 A JP2010216957 A JP 2010216957A JP 2012072232 A JP2012072232 A JP 2012072232A
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- Prior art keywords
- meth
- compound
- acrylate
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 166
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- 239000011737 fluorine Substances 0.000 title claims abstract description 93
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 93
- 239000000203 mixture Substances 0.000 title claims abstract description 56
- 238000000576 coating method Methods 0.000 claims abstract description 82
- 239000011248 coating agent Substances 0.000 claims abstract description 81
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 33
- 125000001033 ether group Chemical group 0.000 claims abstract description 17
- 125000000962 organic group Chemical group 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 93
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 6
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- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- MSLRPWGRFCKNIZ-UHFFFAOYSA-J tetrasodium;hydrogen peroxide;dicarbonate Chemical compound [Na+].[Na+].[Na+].[Na+].OO.OO.OO.[O-]C([O-])=O.[O-]C([O-])=O MSLRPWGRFCKNIZ-UHFFFAOYSA-J 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- NIUZJTWSUGSWJI-UHFFFAOYSA-M triethyl(methyl)azanium;chloride Chemical compound [Cl-].CC[N+](C)(CC)CC NIUZJTWSUGSWJI-UHFFFAOYSA-M 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
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Abstract
【解決手段】下記一般式(1)で表される重合性フッ素系化合物を用いる。
(式中、R1、R2、R3、R4及びR5はそれぞれ独立に水素原子又はメチル基を表し、R6、R7及びR8のうち少なくとも1つは(メタ)アクロイルオキシ骨格を有する基であり、残りは水酸基を表し、X1及びX2はそれぞれ独立に2価の有機基、PFPEはポリ(パーフルオロアルキレンエーテル)鎖を表す。また、nは平均で0〜10の範囲を表す。)
【選択図】なし
Description
試料(1±0.3ミリモル当量)をメチルエチルケトン20mlに溶解させ、セチルトリメチルアンモニウムブロマイドの20質量%酢酸溶液(CTMAB)5mlを加え、クリスタルバイオレット指示薬(酢酸溶液)4〜6滴加え、スターラーでかき混ぜながら0.1mol/l過塩素酸酢酸溶液(0.1mol/l HClO4)で滴定する。0.1mol/l過塩素酸酢酸溶液を1滴加えて青紫色から青色に変化し、青色を1分間持続したところを終点として滴定量を得る。また、溶剤の体積膨張係数は、温度による補正が必要のため、過塩素酸酢酸溶液の温度を記録する。同時に試料を用いない空試験を行って同様に滴定量を測定し、得られた滴定量を用いて下式(2)にしたがってエポキシ当量を求める。
Vs:本試験に要する0.1mol/l HClO4の適定量(ml)
Vb:空試験に要する0.1mol/l HClO4の適定量(ml)
F20:0.1mol/l HClO4の20℃における力価
t :滴定時の0.1mol/l HClO4の液温(℃)
試料1.0gを精秤し、トルエン−メタノール混合溶剤(トルエン70質量部及びメタノール30質量部を混合し、フェノールフタレインを指示薬として、0.1mol/l水酸化カリウムアルコール溶液で中和したもの)30mlに溶解する。フェノールフタレイン指示薬を2〜3滴加え、0.1mol/l水酸化カリウムアルコール溶液(水酸化カリウム7gを純水100mlに溶解した後、エタノールで1000mlとし、2日後に濾過したもの)で滴定する。0.1mol/l水酸化カリウムアルコール溶液を1滴加えて無色から微紅色に変化し、微紅色を30秒間持続したところを終点として滴定量を得る。次いで、得られた滴定量を用いて下式(3)にしたがって酸価を求める。
測定装置:東ソー株式会社製「HLC−8220 GPC」、
カラム:東ソー株式会社製ガードカラム「HHR−H」(6.0mmI.D.×4cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
検出器:ELSD(オルテック製「ELSD2000」)
データ処理:東ソー株式会社製「GPC−8020モデルIIデータ解析バージョン4.30」
測定条件:カラム温度 40℃
展開溶媒 テトラヒドロフラン(THF)
流速 1.0ml/分
試料:樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)。
標準試料:前記「GPC−8020モデルIIデータ解析バージョン4.30」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
東ソー株式会社製「F−288」
東ソー株式会社製「F−550」
株式会社島津製作所製「IRPrestige−21」の測定装置を用いて、試料をKBr板に塗って測定を行った。
試料(1±0.3ミリモル当量)をメチルエチルケトン20mlに溶解させ、セチルトリメチルアンモニウムブロマイドの20質量%酢酸溶液(CTMAB)5mlを加え、クリスタルバイオレット指示薬(酢酸溶液)4〜6滴加え、スターラーでかき混ぜながら0.1mol/l過塩素酸酢酸溶液(0.1mol/l HClO4)で滴定した。0.1mol/l過塩素酸酢酸溶液を1滴加えて青紫色から青色に変化し、青色を1分間持続したところを終点として滴定量を得た。また、溶剤の体積膨張係数は、温度による補正が必要のため、過塩素酸酢酸溶液の温度を記録した。同時に試料を用いない空試験を行って同様に滴定量を測定し、得られた滴定量を用いて下式(2)にしたがってエポキシ当量を求めた。
Vs:本試験に要する0.1mol/l HClO4の適定量(ml)
Vb:空試験に要する0.1mol/l HClO4の適定量(ml)
F20:0.1mol/l HClO4の20℃における力価
t :滴定時の0.1mol/l HClO4の液温(℃)
試料1.0gを精秤し、トルエン−メタノール混合溶剤(トルエン70質量部及びメタノール30質量部を混合し、フェノールフタレインを指示薬として、0.1mol/l水酸化カリウムアルコール溶液で中和したもの)30mlに溶解した。フェノールフタレイン指示薬を2〜3滴加え、0.1mol/l水酸化カリウムアルコール溶液(水酸化カリウム7gを純水100mlに溶解した後、エタノールで1000mlとし、2日後に濾過したもの)で滴定した。0.1mol/l水酸化カリウムアルコール溶液を1滴加えて無色から微紅色に変化し、微紅色を30秒間持続したところを終点として滴定量を得た。次いで、得られた滴定量を用いて下式(3)にしたがって酸価を求めた。
日本電子株式会社製「AL−400」を用いて、試料のアセトン−d6溶液を分析して化合物の構造解析を行った。
測定装置:東ソー株式会社製「HLC−8220 GPC」、
カラム:東ソー株式会社製ガードカラム「HHR−H」(6.0mmI.D.×4cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
検出器:ELSD(オルテック製「ELSD2000」)
データ処理:東ソー株式会社製「GPC−8020モデルIIデータ解析バージョン4.30」
測定条件:カラム温度 40℃
展開溶媒 テトラヒドロフラン(THF)
流速 1.0ml/分
試料:樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)。
標準試料:前記「GPC−8020モデルIIデータ解析バージョン4.30」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
東ソー株式会社製「F−288」
東ソー株式会社製「F−550」
撹拌装置、温度計、冷却管及び滴下装置を備えたガラスフラスコに、下記式(a2−1−1)で表される両末端に水酸基を有するパーフルオロポリエーテル化合物(以下、「化合物(a2−1−1)と略記する。水酸基当量は、740g/eq)50質量部、エピクロロヒドリン62.5質量部及びエタノール20質量部を仕込んだ。次いで、窒素気流下で攪拌を開始し、フラスコ内温度を50℃に保ちながら、49質量%水酸化ナトリウム水溶液8.3質量部を2時間かけて滴下した。滴下終了後、60℃まで昇温して3時間攪拌した後、室温に戻した。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、実施例1で得られた化合物(a4−1−1)22.9質量部、重合禁止剤としてp−メトキシフェノール0.01質量部、ウレタン化触媒としてジブチルスズジラウレート0.01質量部を仕込み、空気気流下で攪拌を開始し、80℃に昇温した。その後、2−アクリロイルオキシエチルイソシアネート(以下、「AOI」と略記する。)3.4質量部を発熱に注意しながら分割して添加した。AOIを添加終了後、80℃で6時間攪拌することにより反応を行い、IRスペクトル測定でイソシアネート基由来の2360cm−1付近の吸収ピークの消失を確認した後、重合性フッ素系化合物(2)26質量部を得た。この重合性フッ素系化合物(2)は粘稠液状であった。得られた重合性フッ素系化合物(2)の分子量をGPC(ポリスチレン換算分子量)で測定した結果、数平均分子量1,700、重量平均分子量1,900であった。また、フッ素含有率は44質量%であった。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、実施例1で得られた化合物(a4−1−1)22.9質量部、重合禁止剤としてp−メトキシフェノール0.01質量部、ウレタン化触媒としてジブチルスズジラウレート0.01質量部を仕込み、空気気流下で攪拌を開始し、80℃に昇温した。その後、2−メタクリロイルオキシエチルイソシアネート(以下、「MOI」と略記する。)3.4質量部を発熱に注意しながら分割して添加した。MOIを添加終了後、80℃で6時間攪拌することにより反応を行い、IRスペクトル測定でイソシアネート基由来の2360cm−1付近の吸収ピークの消失を確認した後、重合性フッ素系化合物(3)26.3質量部を得た。この重合性フッ素系化合物(3)は粘稠液状であった。得られた重合性フッ素系化合物(3)の分子量をGPC(ポリスチレン換算分子量)で測定した結果、数平均分子量1,800、重量平均分子量2,000であった。また、フッ素含有率は43質量%であった。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、溶媒としてメチルイソブチルケトン100質量部を仕込み、窒素気流下にて攪拌しながら105℃に昇温した。次いで、下記式(3)で表されるフッ素化アルキル基を有するアクリレート50質量部、及び下記式(4)で表されるエチレンオキシド鎖及びプロピレンオキシド鎖を有するアクリレート50質量部をメチルイソブチルケトン150質量部に溶解した単量体溶液250質量部と、ラジカル重合開始剤としてt−ブチルペルオキシ−2−エチルヘキサノエート5質量部をメチルイソブチルケトン50質量部に溶解した重合開始剤溶液65質量部との2種類の滴下液をそれぞれ別々の滴下装置にセットし、フラスコ内を105℃に保ちながら同時に3時間かけて滴下した。滴下終了後、105℃で10時間攪拌して重合を完了した後、減圧下で溶媒の一部を留去し、フッ素系界面活性剤(H1)を50質量%含有するメチルイソブチルケトン溶液204部を得た。得られたフッ素系界面活性剤(H1)の分子量をGPC(ポリスチレン換算分子量)で測定した結果、数平均分子量4,000、重量平均分子量10,000であった。また、フッ素含有率は32質量%であった。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、前記化合物(a2−1−1)20質量部、溶媒としてジイソプロピルエーテル20質量部、重合禁止剤としてp−メトキシフェノール0.02質量部及び中和剤としてトリエチルアミン3.1質量部を仕込み、空気気流下にて攪拌を開始し、フラスコ内を10℃に保ちながらアクリル酸クロライド2.7質量部を1時間かけて滴下した。滴下終了後、10℃で1時間攪拌し、昇温して30℃で1時間攪拌した後、50℃に昇温して10時間攪拌することにより反応を行い、ガスクロマトグラフィー測定にてアクリル酸クロライドの消失が確認された。次いで、溶媒としてジイソプロピルエーテル40質量部を追加した後、イオン交換水80質量部を混合して攪拌してから静置し水層を分離させて取り除く方法による洗浄を3回繰り返した。次いで、重合禁止剤としてp−メトキシフェノール0.02質量部を添加し、脱水剤として硫酸マグネシウム8部を添加して1日間静置することで完全に脱水した後、脱水剤を濾別した。次いで、減圧下で溶媒を留去することによって、下記式(5)で表されるパーフルオロポリエーテル鎖の両末端にアクリロイル基を有する化合物21.5質量部を得た。
紫外線硬化型ウレタンアクリレート樹脂(DIC株式会社製「ユニディック17−806」;樹脂分80質量%の酢酸ブチル溶液)125質量部、光重合開始剤として1−ヒドロキシシクロヘキシルフェニルケトン(BASFジャパン株式会社製「イルガキュア184」)5質量部、溶剤としてトルエン54質量部、2−プロパノール28質量部、酢酸エチル28質量部、プロピレングリコールモノメチルエーテル28質量部を混合し溶解させて、活性エネルギー線硬化型組成物のベース樹脂組成物を得た。
上記で得られたベース樹脂組成物268質量部に、含フッ素界面活性剤として実施例1〜3で得られた重合性フッ素系化合物(1)〜(3)、比較例1〜2で得られたフッ素系界面活性剤(H1)及び重合性フッ素系化合物(H2)を固形分として1質量部となる量を加えて均一に混合して、活性エネルギー線硬化型組成物を得た。次いで、この活性エネルギー線硬化型組成物をバーコーターNo.13を用いて、厚さ188μmのポリエチレンテレフタレート(PET)フィルムに塗布した後、60℃の乾燥機に5分間入れて溶剤を揮発させた。次に、乾燥した塗膜に紫外線硬化装置(窒素雰囲気下、高圧水銀灯、紫外線照射量2kJ/m2)で紫外線(UV)を照射して硬化させ、実施例4〜6及び比較例3〜4として塗工フィルムを作製した。また、何も添加せずに活性エネルギー線硬化型組成物のベース樹脂組成物のみについても同様に塗工フィルムを作製して比較例5とした。
上記で得られた塗工フィルムの塗工表面の防汚性を、下記の水及びn−ドデカンの接触角及び汚れ付着防止性から評価した。
塗工フィルムの塗工表面について、接触角測定装置(協和界面科学株式会社製「MODEL CA−W150」)を用いて、水及びn−ドデカンの接触角を測定した。
塗工フィルムの塗工表面に、フェルトペン(三菱鉛筆株式会社製「ユニ・メディアックス」黒色)で線を描き、その黒色インクの付着状態を目視で観察することで汚れ付着防止性の評価を行った。なお、評価基準は下記の通りである。
AA:防汚性が最も良好で、インクが玉状にはじくもの。
A:インクが玉状にはじかず、線状のはじきが生じるもの(線幅がフェルトペンのペン先の幅の50%未満)。
B:インクの線状のはじきが生じ、線幅がフェルトペンのペン先の幅の50%以上100%未満であったもの。
C:インクがまったくはじかずに表面にきれいに描けてしまうもの。
防汚持続性の評価として、塗膜表面を磨耗処理した塗工フィルムについて、水及びn−ドデカンの接触角の測定、汚れ付着防止性の評価を上記と同様に行った。なお、磨耗処理は、往復磨耗試験機(新東科学株式会社製「HEIDON トライボギア TYPE:30S」)を用いて、治具に不織布(旭化成せんい株式会社製「ベンコットS」)を取り付けて1.72N/cm2の荷重にて、5000回の往復磨耗することにより行った。
Claims (4)
- 請求項1記載の重合性フッ素系化合物、及び、活性エネルギー線硬化型樹脂(B)又は活性エネルギー線硬化性単量体(C)を含有することを特徴とする活性エネルギー線硬化型組成物。
- 請求項1記載の重合性フッ素系化合物又は請求項2記載の活性エネルギー線硬化型組成物を、基材に塗布し、活性エネルギー線を照射して硬化させてなることを特徴とする硬化物。
- 請求項1記載の重合性フッ素系化合物又は請求項2記載の活性エネルギー線硬化型組成物の硬化塗膜を有することを特徴とする物品。
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JP2014070165A (ja) * | 2012-09-28 | 2014-04-21 | Fujifilm Corp | 重合性組成物、それを用いた、反射防止フィルム、偏光板、及び画像表示装置、並びに撥水ないし撥油膜 |
JP2014167596A (ja) * | 2012-03-30 | 2014-09-11 | Fujifilm Corp | 重合性組成物、それを用いた、反射防止フィルム、偏光板、及び画像表示装置 |
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