JP6079023B2 - 活性エネルギー線硬化性組成物及びフィルムの製造方法 - Google Patents
活性エネルギー線硬化性組成物及びフィルムの製造方法 Download PDFInfo
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- JP6079023B2 JP6079023B2 JP2012160465A JP2012160465A JP6079023B2 JP 6079023 B2 JP6079023 B2 JP 6079023B2 JP 2012160465 A JP2012160465 A JP 2012160465A JP 2012160465 A JP2012160465 A JP 2012160465A JP 6079023 B2 JP6079023 B2 JP 6079023B2
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- meth
- acrylate
- active energy
- silica particles
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- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical group C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims description 8
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
- C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/103—Esters of polyhydric alcohols or polyhydric phenols of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
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- C08K3/00—Use of inorganic substances as compounding ingredients
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- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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Description
粒子形状は、電界放射型走査電子顕微鏡(FE−SEM)(例えば、日本電子社製「JSM6700」)を用いて観察することで確認できる。
平均粒子径は、電界放射型走査電子顕微鏡(FE−SEM)(例えば、日本電子社製「JSM6700」)を用いて観察することで確認できる。
平均細孔径は、細孔分布測定装置(例えば、株式会社島津製作所「ASAP2020」)を用いて測定できる。
比表面積は、細孔分布測定装置(例えば、株式会社島津製作所「ASAP2020」)を用いてBET法により測定できる。
体積平均径は、レーザードップラー法を用いた粒度分布計(例えば、大塚電子株式会社製「ゼータ電位・粒径測定システム ELSZ−2」)を用いて測定できる。また、変動係数は、同装置で測定した体積平均径及び標準偏差から、上記式(1)によって求められる。
細孔径分布のピークは、細孔分布測定装置(例えば、株式会社島津製作所「ASAP2020」)を用いて測定でき、得られた細孔径分布のピーク値である。
粒子形状は、電界放射型走査電子顕微鏡(FE−SEM)(日本電子社製「JSM6700」)を用いて、5万倍で観察することで確認した。
体積平均径は、レーザードップラー法を用いた粒度分布計(大塚電子株式会社製「ゼータ電位・粒径測定システム ELSZ−2」)を用いて測定した。また、変動係数は、同装置で測定した体積平均径及び標準偏差から、下記式(1)によって求めた。なお、下記式(1)中の標準偏差は、下記式(2)で求めた。また、下記式(2)中のd84%は体積粒度分布における84%径を表し、d16%は体積粒度分布における16%径を表す。
細孔径分布のピークは、細孔分布測定装置(株式会社島津製作所「ASAP2020」)を用いて測定して得られた細孔分布のピーク値とした。
比表面積は、細孔分布測定装置(株式会社島津製作所「ASAP2020」)を用いてBET法により測定した。
温度計、攪拌羽根を備えた500mLの4口フラスコに、メタノール213.2g、純水61.3g及び28質量%アンモニア水27.4gを仕込み、攪拌により均一に混合し(II液)、内温を20℃に保った。また、別の容器でテトラメトキシシラン34.3g、メタノール45.1g及びラウリルアミン9.3gを均一に混合した(I液)。フラスコ内を20℃に保ちながら、I液を120分かけてII液中へ注入した。I液の注入終了後、20℃で60分間反応を継続した。反応終了後、反応液を10,000rpmで10分間遠心分離した後、上澄み液を廃棄して沈殿物を取り出した。
合成例1で得られた多孔質シリカ粒子(1)の分散液227.8質量部(多孔質シリカ粒子(1)18質量部含有)、多官能アクリレートの混合物(ジペンタエリスリトールペンタアクリレート(以下、「DPPA」と略記する。)55質量%及びジペンタエリスリトールヘキサアクリレート(以下、「DPHA」と略記する。)45質量%の混合物;以下、「多官能アクリレート(1)」と略記する。)364質量部、光重合開始剤(BASFジャパン株式会社製「イルガキュア184」、1−ヒドロキシシクロヘキシルフェニルケトン;以下、「Irg.184」と略記する。)18質量部及びイソプロパノール390.2質量部を均一に混合して、活性エネルギー線硬化性組成物(1)を得た。
実施例1で用いた多官能アクリレート(1)に代えて、多官能アクリレートの混合物(DPPA 35質量%及びDPHA 65質量%の混合物;以下、「多官能アクリレート(2)」と略記する。)364質量部を用いた以外は実施例1と同様に行い、活性エネルギー線硬化性組成物(2)を得た。
実施例1で用いた多官能アクリレート(1)に代えて、多官能アクリレートの混合物(ペンタエリスリトールトリアクリレート(以下、「PE3A」と略記する。)70質量%及びペンタエリスリトールテトラアクリレート(以下、「PE4A」と略記する。)30質量%の混合物;以下、「多官能アクリレート(3)」と略記する。)364質量部を用いた以外は実施例1と同様に行い、活性エネルギー線硬化性組成物(3)を得た。
実施例1で用いた多官能アクリレート(1)に代えて、多官能アクリレートの混合物(PE3A 60質量%及びPE4A 40質量%の混合物;以下、「多官能アクリレート(4)」と略記する。)364質量部を用いた以外は実施例1と同様に行い、活性エネルギー線硬化性組成物(4)を得た。
実施例1で用いた多官能アクリレート(1)に代えて、多官能アクリレートの混合物(PE3A 30質量%及びPE4A 70質量%の混合物;以下、「多官能アクリレート(5)」と略記する。)364質量部を用いた以外は実施例1と同様に行い、活性エネルギー線硬化性組成物(5)を得た。
実施例1で用いた多孔質シリカ粒子(1)に代えて、中実シリカ(日本触媒株式会社製「シーホスター KE−P10」、粒子径100〜200nm、表面未処理)18質量部を用い、イソプロパノールの配合量を390.2質量部から600質量部に変更した以外は実施例1と同様に行い、活性エネルギー線硬化性組成物(R1)を得た。
実施例1で用いた多孔質シリカ粒子(1)に代えて、中実シリカ(日本触媒株式会社製「シーホスター KE−P100」、粒子径900〜1,300nm、表面未処理)18質量部を用い、イソプロパノールの配合量を390.2質量部から600質量部に変更した以外は実施例1と同様に行い、活性エネルギー線硬化性組成物(R2)を得た。
実施例1で用いた多官能アクリレート(1)に代えて、エチレンオキサイド変性トリメチロールプロパントリアクリレート(トリメチロールプロパンにエチレンオキサイドを3モル付加したトリアクリレート;以下、「EO−TMPTA」と略記する。)364質量部を用いた以外は実施例1と同様に行い、活性エネルギー線硬化性組成物(R3)を得た。
実施例1で用いた多官能アクリレート(1)に代えて、ジトリメチロールプロパンテトラアクリレート(以下、「DTMPTA」と略記する。)364質量部を用いた以外は実施例1と同様に行い、活性エネルギー線硬化性組成物(R4)を得た。
[評価用フィルムの作製]
上記の実施例1で得られた活性エネルギー線硬化性組成物(1)を、厚さ100μmのポリエチレンテレフタレート(PET)フィルム基材上に、ワイヤーバーコーター#24を用いて塗工し、25℃で10秒間乾燥した後、80℃の乾燥機で1分間乾燥した。その後、紫外線硬化装置(窒素雰囲気下、フュージョンランプ(Hバルブ、紫外線照射量300J/m2)を用いて硬化させ、評価用フィルムを作製した。
上記で得られた評価用フィルムの硬化塗膜表面同士、又は評価用フィルムの硬化塗膜表面と基材面(硬化塗膜の反対面)とを接触させ、アンチブロッキング性を下記の5段階の基準にしたがって評価した。
5:引っかからない。
4:強く擦るとわずかに引っかかる。
3:弱く擦るとわずかに引っかかる。
2:引っかかる。
1:張り付いてしまう。
上記で得られた評価用フィルムについて、ヘイズメーター(日本電色工業株式会社製「NDH2000」)で測定し、得られたヘイズ値から、下記の5段階の基準にしたがって透明性を評価した。
5:ヘイズ値が0.5未満である。
4:ヘイズ値が0.5以上1.0未満である。
3:ヘイズ値が1.0以上5.0未満である。
2:ヘイズ値が5.0以上10.0未満である。
1:ヘイズ値が10.0以上である。
上記の実施例2〜5及び比較例1〜4で得られた活性エネルギー線硬化性組成物(2)〜(5)及び(R1)〜(R4)を用いて、実施例6と同様に操作して、評価用フィルムを作製後、アンチブロッキング性及び透明性の評価を行った。
Claims (6)
- テトラアルコキシシラン、アルキルアミン及びアルコールを含む混合液(I液)を、アンモニア、アルコール及び水を含む混合液(II液)に加え、テトラアルコキシシランの加水分解及び縮合反応によりシリカ粒子を得て、該シリカ粒子からアルキルアミンを除去することで表面に細孔を有する多孔質シリカ粒子(A)を得た後、水酸基を有する多官能(メタ)アクリレート(B)と混合することを特徴とする活性エネルギー線硬化性組成物の製造方法。
- 前記多孔質シリカ粒子(A)が、ヘキサメチルジシラザンで表面修飾されたものである請求項1記載の活性エネルギー線硬化性組成物の製造方法。
- 前記多官能(メタ)アクリレート(B)が、ペンタエリスリトールトリ(メタ)アクリレート及び/又はジペンタエリスリトールペンタ(メタ)アクリレートである請求項1又は2記載の活性エネルギー線硬化性組成物の製造方法。
- 水酸基を有する多官能(メタ)アクリレート(B)と水酸基を有しない多官能(メタ)アクリレート(C)との質量比[(B)/(C)]が、10/90〜90/10の範囲である請求項1〜3のいずれか1項記載の活性エネルギー線硬化性組成物の製造方法。
- 請求項1〜4のいずれか1項記載の活性エネルギー線硬化性組成物の製造方法により得られた活性エネルギー線硬化性組成物を硬化することを特徴とする硬化物の製造方法。
- 基材フィルムの少なくとも一面に、請求項1〜4のいずれか1項記載の活性エネルギー線硬化性組成物の製造方法により得られた活性エネルギー線硬化性組成物の硬化塗膜を形成することを特徴とするフィルムの製造方法。
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JP2012160465A JP6079023B2 (ja) | 2012-07-19 | 2012-07-19 | 活性エネルギー線硬化性組成物及びフィルムの製造方法 |
KR1020130082633A KR20140011948A (ko) | 2012-07-19 | 2013-07-15 | 활성 에너지선 경화성 조성물 및 그것을 이용한 필름 |
CN201310298236.3A CN103571240A (zh) | 2012-07-19 | 2013-07-16 | 活性能量线固化性组合物及使用其的膜 |
TW102125823A TW201412896A (zh) | 2012-07-19 | 2013-07-18 | 活性能量線硬化性組合物及使用其之薄膜 |
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JP7479189B2 (ja) * | 2020-05-07 | 2024-05-08 | サカタインクス株式会社 | ブラックマトリックス用顔料分散組成物、およびブラックマトリックス用顔料分散レジスト組成物 |
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JPH01230421A (ja) * | 1988-03-11 | 1989-09-13 | Nippon Shokubai Kagaku Kogyo Co Ltd | 多孔質球状シリカ微粒子 |
JP3048276B2 (ja) * | 1992-04-23 | 2000-06-05 | 松下電工株式会社 | エアロゲルの製造方法 |
JP3761189B2 (ja) * | 1993-11-04 | 2006-03-29 | 触媒化成工業株式会社 | 複合酸化物ゾル、その製造方法および基材 |
JP4642165B2 (ja) * | 1997-08-07 | 2011-03-02 | 日揮触媒化成株式会社 | 多孔質シリカ系被膜形成用塗布液、被膜付基材および短繊維状シリカ |
JP2004099361A (ja) * | 2002-09-09 | 2004-04-02 | Mitsui Chemicals Inc | 耐水性多孔質シリカの製造方法、及びその用途 |
JP2006306008A (ja) * | 2005-03-31 | 2006-11-09 | Jsr Corp | 帯電防止用積層体 |
JP2006348171A (ja) * | 2005-06-16 | 2006-12-28 | Toppan Printing Co Ltd | 低屈折率コーティング用硬化性樹脂組成物、反射防止フィルム |
JP2008024808A (ja) * | 2006-07-20 | 2008-02-07 | Jsr Corp | 硬化性組成物及びその硬化物 |
EP2181069B1 (en) * | 2007-07-13 | 2020-04-29 | University College Cork-National University of Ireland, Cork | A method for synthesising porous silica microparticles |
JP4961369B2 (ja) * | 2008-02-27 | 2012-06-27 | 富士フイルム株式会社 | 光学フィルム、偏光板、画像表示装置および光学フィルムの製造方法 |
MY192479A (en) * | 2008-10-17 | 2022-08-23 | Showa Denko Materials Co Ltd | Film having low refractive index film and method for producing the same, anti-reflection film and method for producing the same, coating liquid set for low refractive index film, substrate having microparticle-laminated thin film and method for producing the same, and optical member |
JP5302089B2 (ja) * | 2008-12-26 | 2013-10-02 | 日東電工株式会社 | 無機多孔質体の製造方法 |
JP2010180375A (ja) * | 2009-02-09 | 2010-08-19 | Shin-Etsu Chemical Co Ltd | 光硬化型コーティング剤組成物、被膜形成方法及び被覆物品 |
JP2010195604A (ja) * | 2009-02-23 | 2010-09-09 | Toyota Tsusho Corp | 表面改質多孔性シリカの製造方法、表面改質多孔性シリカ、樹脂添加用スラリー組成物、樹脂用充填剤及び樹脂組成物 |
JP2011039363A (ja) * | 2009-08-14 | 2011-02-24 | Sumitomo Chemical Co Ltd | 偏光板および液晶パネル |
JP5358355B2 (ja) * | 2009-08-28 | 2013-12-04 | 豊田通商株式会社 | 樹脂組成物及び金属樹脂積層体の製造方法 |
US20140011954A1 (en) * | 2011-01-21 | 2014-01-09 | Dic Corporation | Method for producing porous silica particle, resin composition for antireflection coating, and article and antireflection film having antireflection coating |
-
2012
- 2012-07-19 JP JP2012160465A patent/JP6079023B2/ja active Active
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2013
- 2013-07-15 KR KR1020130082633A patent/KR20140011948A/ko not_active Application Discontinuation
- 2013-07-16 CN CN201310298236.3A patent/CN103571240A/zh active Pending
- 2013-07-18 TW TW102125823A patent/TW201412896A/zh unknown
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JP2014019807A (ja) | 2014-02-03 |
KR20140011948A (ko) | 2014-01-29 |
CN103571240A (zh) | 2014-02-12 |
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