JP2007269978A - フッ素系界面活性剤及びそれを用いた感光性組成物 - Google Patents
フッ素系界面活性剤及びそれを用いた感光性組成物 Download PDFInfo
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- JP2007269978A JP2007269978A JP2006097455A JP2006097455A JP2007269978A JP 2007269978 A JP2007269978 A JP 2007269978A JP 2006097455 A JP2006097455 A JP 2006097455A JP 2006097455 A JP2006097455 A JP 2006097455A JP 2007269978 A JP2007269978 A JP 2007269978A
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- coating
- fluorine
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- blemmer
- compound
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- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 22
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- 125000005010 perfluoroalkyl group Chemical group 0.000 abstract description 9
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- DWWMSEANWMWMCB-UHFFFAOYSA-N tribromomethylsulfonylbenzene Chemical compound BrC(Br)(Br)S(=O)(=O)C1=CC=CC=C1 DWWMSEANWMWMCB-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- VMJFYMAHEGJHFH-UHFFFAOYSA-M triphenylsulfanium;bromide Chemical compound [Br-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 VMJFYMAHEGJHFH-UHFFFAOYSA-M 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 230000004304 visual acuity Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011850 water-based material Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Abstract
【解決手段】 下記一般式(1)
−[OCF2CF(CF3)]n−OCF3・・・・・(1)
(式中、nは1〜10の整数を示す。)
で表されるフッ素化ポリオキシプロピレン鎖を有する化合物(A)からなることを特徴とするフッ素系界面活性剤、及びこれを用いた感光性組成物。
【選択図】 なし
Description
−[OCF2CF(CF3)]n−OCF3・・・・・(1)
(式中、nは1〜10の整数を示す。)
で表されるフッ素化ポリオキシプロピレン鎖を有する化合物(A)からなることを特徴とするフッ素系界面活性剤、及びそれを含有する感光性組成物を提供するものである。
−[OCF2CF(CF3)]n−OCF3・・・・・(1)
(式中、nは1〜10の整数を示す。)
で表されるフッ素化ポリオキシプロピレン鎖を有する化合物(A)からなることを特徴とする。
で表される単量体(a1)と、その他の単量体(a2)との共重合体であることが好ましい。
で表される単量体を挙げることができる。
攪拌装置、コンデンサー、温度計を備えたガラスフラスコに単量体(a1−1)19重量部、分子量1100のエチレンオキシドとプロピレンオキシドとの共重合体を側鎖に持つモノアクリレート化合物81重量部、そしてイソプロピルアルコール(以下、IPAと略す)400重量部を仕込み、窒素ガス気流中、還流下で重合開始剤としてアゾビスイソブチロニトリル(以下、AIBNと略す)0.7重量部と、連鎖移動剤としてラウリルメルカプタン10重量部を添加した後、70℃にて7時間加熱し重合を行った。この共重合体のゲルパーミエーショングラフ(以後GPCと略す)によるポリスチレン換算分子量はMw=6,200であった。この共重合体をフッ素系界面活性剤1とする。
合成例1で用いた単量体(a1−1)を下記構造式(4)
C8F17CH2CH2OCOCH=CH2・・・・(4)
で示されるフッ素化アルキル基含有アクリレートに置き換えた以外は、合成例1と同様にしてフッ素系界面活性剤2を得た。GPCによるこの共重合体の重量平均分子量(ポリスチレン換算)はMw=6,800であった。
攪拌装置、コンデンサー、温度計を備えたガラスフラスコに単量体(a1−1)21重量部、シリコーン鎖含有エチレン性不飽和単量体(チッソ株式会社製、サイラプレーンTM−0701)12重量部、分子量1100のエチレンオキシドとプロピレンオキシドとの共重合体を側鎖に持つモノアクリレート化合物55重量部、テトラエチレングリコールの両末端がメタクリレート化された化合物(新中村化学工業株式会社製、NKエステル4G)4重量部、メチルメタクリレート8重量部、そしてIPA350重量部を仕込み、窒素ガス気流中、還流下で重合開始剤としてAIBNを1重量部と連鎖移動剤としてラウリルメルカプタン10重量部を添加した後、70℃にて8時間還流し重合を完成させた。GPCによるこの共重合体の重量平均分子量(ポリスチレン換算)はMw=6,500であった。
合成例3で用いた単量体(a1−1)を前記構造式(4)で示されるフッ素化アルキル基含有アクリレートに置き換えた以外は、合成例3と同様にしてフッ素系界面活性剤4を得た。GPCによるこの高分子化合物の重量平均分子量(ポリスチレン換算)はMw=6,500であった。
合成例1〜4で示した分子量1100のエチレンオキシドとプロピレンオキシドとの共重合体を側鎖に持つモノアクリレート化合物は、次のようにして合成した。トルエン溶液60重量部下、プルロニック化合物(旭電化工業株式会社製、アデカプルロニックL31)100重量部、アクリル酸4.6重量部、硫酸6.4重量部、メトキノン0.2重量部を添加して還流下12時間反応させ、酸を水洗除去によって除いた後、脱溶剤を行って目的物を得た。
合成例1〜2で得られたフッ素系界面活性剤1及び2を用いて、以下のような評価を実施し、その結果を表1に記載する。
水溶性:水に対して、得られたフッ素系界面活性剤を溶液重量に対して0.1重量%、1.0重量%、5.0重量%、10重量%添加して、析出物の有無を目視により観察することによって、水への溶解性を調べた。
○: 析出物が生じない。
×: 析出物が生じる。
<フェノールノボラック樹脂溶液の調製方法と塗膜作成方法>
フェノライトKA−105L(大日本インキ化学工業株式会社製)125重量部をプロピレングリコールモノエチルアセテート375重量部に溶解して樹脂溶液を調製し、これに合成例3及び4で得られたフッ素系界面活性剤を、該樹脂溶液中の固形分に対して0.4重量%の濃度になる様に添加し、1μmのPTFE製フィルターで精密濾過して組成物を調製した。この組成物を縦、横10×10cmのCr基板上に回転数3000rpmでスピンコーティングした後、ホットプレート上にて90秒間加熱して溶媒を除去し、膜厚が1.5μmのレジスト膜を有する塗膜基板を得た。得られた塗膜の外観を目視にて評価した結果を表2に示す。
ストリエーション:ナトリウムランプを使用して、ストリエーションの発生状況を目視にて観察した。
○: ストリエーションの発生が認められないもの。
△: ストリエーションの発生がやや認められるもの。
×: ストリエーションの発生が顕著に認められるもの。
モヤムラとは、塗布した基板表面に現れる波状の塗布ムラのことである。
○: モヤムラの発生が認められないもの。
△: モヤムラの発生がやや認められるもの。
×: モヤムラの発生が顕著に認められるもの。
○: チャック跡の発生が認められないもの。
△: チャック跡の発生がやや認められるもの。
×: チャック跡の発生が顕著に認められるもの。
Claims (5)
- 下記一般式(1)
−[OCF2CF(CF3)]n−OCF3・・・・・(1)
(式中、nは1〜10の整数を示す。)
で表されるフッ素化ポリオキシプロピレン鎖を有する化合物(A)からなることを特徴とするフッ素系界面活性剤。 - その他の単量体(a2)がポリオキシアルキレン鎖含有エチレン性不飽和単量体(x1)を含む請求項3記載のフッ素系界面活性剤。
- 共重合体の重量平均分子量が3,000〜50,000である請求項2又は3に記載のフッ素系界面活性剤。
- 請求項1〜4のいずれか1項記載のフッ素系界面活性剤を含有することを特徴とする感光性組成物。
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Cited By (4)
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JP2009007488A (ja) * | 2007-06-28 | 2009-01-15 | Chisso Corp | フッ素系重合体および樹脂組成物 |
JP2012062433A (ja) * | 2010-09-17 | 2012-03-29 | Dic Corp | フッ素系界面活性剤、それを用いたコーティング組成物及びレジスト組成物 |
JP2017088786A (ja) * | 2015-11-13 | 2017-05-25 | Dic株式会社 | フッ素系界面活性剤およびこれを含有する組成物 |
WO2019198425A1 (ja) * | 2018-04-12 | 2019-10-17 | 第一工業製薬株式会社 | 親水撥油剤 |
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JPH10287719A (ja) * | 1997-04-08 | 1998-10-27 | Ausimont Spa | フッ素化変性水素含有重合体、その製法、変性剤およびその応用 |
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JP2009007488A (ja) * | 2007-06-28 | 2009-01-15 | Chisso Corp | フッ素系重合体および樹脂組成物 |
JP2012062433A (ja) * | 2010-09-17 | 2012-03-29 | Dic Corp | フッ素系界面活性剤、それを用いたコーティング組成物及びレジスト組成物 |
JP2017088786A (ja) * | 2015-11-13 | 2017-05-25 | Dic株式会社 | フッ素系界面活性剤およびこれを含有する組成物 |
WO2019198425A1 (ja) * | 2018-04-12 | 2019-10-17 | 第一工業製薬株式会社 | 親水撥油剤 |
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