JP5793855B2 - 光硬化性接着剤及び表示素子 - Google Patents
光硬化性接着剤及び表示素子 Download PDFInfo
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- JP5793855B2 JP5793855B2 JP2010265613A JP2010265613A JP5793855B2 JP 5793855 B2 JP5793855 B2 JP 5793855B2 JP 2010265613 A JP2010265613 A JP 2010265613A JP 2010265613 A JP2010265613 A JP 2010265613A JP 5793855 B2 JP5793855 B2 JP 5793855B2
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- Prior art keywords
- acrylate
- meth
- adhesive
- photocurable adhesive
- photocurable
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- 239000003999 initiator Substances 0.000 claims description 12
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- 229920001577 copolymer Polymers 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
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- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 18
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- 125000000217 alkyl group Chemical group 0.000 description 7
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- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
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- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
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- C09J11/08—Macromolecular additives
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- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
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- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
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Description
本発明の光硬化性接着剤は、セルロース誘導体(A)、光硬化性媒体、及び光重合開始剤(C)を含有する光硬化性接着剤である。
本発明に使用されるセルロース誘導体(A)は式(I)で表される。セルロース誘導体(A)には、本発明における光硬化性媒体に溶解する化合物を用いることができる。セルロース誘導体(A)は一種でも二種以上でもよい。
本発明に使用される光硬化性媒体は、透明の液体であり、セルロース誘導体(A)及び光重合開始剤(C)、及び必要に応じてさらに添加される他の成分を溶解する溶解性を有し、かつ光重合によって硬化する材料である。光硬化性媒体は一種でも二種以上でもよい。このような光硬化性媒体としては、例えば、ラジカル重合性モノマー(B)、充填剤(D)、ラジカル重合性又は光架橋性を有するオリゴマー、及び、ラジカル重合性又は光架橋性を有するポリマーが挙げられる。
光重合開始剤(C)は、紫外線又は可視光線の照射によりラジカルを発生する化合物であれば特に限定されない。光重合開始剤(C)は一種でも二種以上でもよい。光重合開始剤(C)としては、例えば、ベンゾフェノン、ミヒラーズケトン、4,4’−ビス(ジエチルアミノ)ベンゾフェノン、キサントン、チオキサントン、イソプロピルキサントン、2,4−ジエチルチオキサントン、2−エチルアントラキノン、アセトフェノン、2−ヒドロキシ−2−メチルプロピオフェノン、2−ヒドロキシ−2−メチル−4’−イソプロピルプロピオフェノン、1−ヒドロキシシクロヘキシルフェニルケトン、イソプロピルベンゾインエーテル、イソブチルベンゾインエーテル、2,2−ジエトキシアセトフェノン、2,2−ジメトキシ−2−フェニルアセトフェノン、カンファーキノン、ベンズアントロン、2−メチル−1−[4−(メチルチオ)フェニル]−2−モルホリノプロパン−1−オン、2−ベンジル−2−ジメチルアミノ−1−(4−モルホリノフェニル)−ブタノン−1、4−ジメチルアミノ安息香酸エチル、4−ジメチルアミノ安息香酸イソアミル、4,4’−ジ(t−ブチルペルオキシカルボニル)ベンゾフェノン、3,4,4’−トリ(t−ブチルペルオキシカルボニル)ベンゾフェノン、3,3’,4,4’−テトラ(t−ブチルペルオキシカルボニル)ベンゾフェノン、3,3’,4,4’−テトラ(t−ヘキシルペルオキシカルボニル)ベンゾフェノン、3,3’−ジ(メトキシカルボニル)−4,4’−ジ(t−ブチルペルオキシカルボニル)ベンゾフェノン、3,4’−ジ(メトキシカルボニル)−4,3’−ジ(t−ブチルペルオキシカルボニル)ベンゾフェノン、4,4’−ジ(メトキシカルボニル)−3,3’−ジ(t−ブチルペルオキシカルボニル)ベンゾフェノン、1,2−オクタンジオン,1−[4−(フェニルチオ)フェニル]−,2−(o−ベンゾイルオキシム)、2−(4’−メトキシスチリル)−4,6−ビス(トリクロロメチル)−s−トリアジン、2−(3’,4’−ジメトキシスチリル)−4,6−ビス(トリクロロメチル)−s−トリアジン、2−(2’,4’−ジメトキシスチリル)−4,6−ビス(トリクロロメチル)−s−トリアジン、2−(2’−メトキシスチリル)−4,6−ビス(トリクロロメチル)−s−トリアジン、2−(4’−ペンチルオキシスチリル)−4,6−ビス(トリクロロメチル)−s−トリアジン、4−[p−N,N−ジ(エトキシカルボニルメチル)]−2,6−ジ(トリクロロメチル)−s−トリアジン、1,3−ビス(トリクロロメチル)−5−(2’−クロロフェニル)−s−トリアジン、1,3−ビス(トリクロロメチル)−5−(4’−メトキシフェニル)−s−トリアジン、2−(p−ジメチルアミノスチリル)ベンズオキサゾール、2−(p−ジメチルアミノスチリル)ベンズチアゾール、2−メルカプトベンゾチアゾール、3,3’−カルボニルビス(7−ジエチルアミノクマリン)、2−(o−クロロフェニル)−4,4’,5,5’−テトラフェニル−1,2’−ビイミダゾール、2,2’−ビス(2−クロロフェニル)−4,4’,5,5’−テトラキス(4−エトキシカルボニルフェニル)−1,2’−ビイミダゾール、2,2’−ビス(2,4−ジクロロフェニル)−4,4’,5,5’−テトラフェニル−1,2’−ビイミダゾール、2,2’−ビス(2,4−ジブロモフェニル)−4,4’,5,5’−テトラフェニル−1,2’−ビイミダゾール、2,2’−ビス(2,4,6−トリクロロフェニル)−4,4’,5,5’−テトラフェニル−1,2’−ビイミダゾール、3−(2−メチル−2−ジメチルアミノプロピオニル)カルバゾール、3,6−ビス(2−メチル−2−モルホリノプロピオニル)−9−n−ドデシルカルバゾール、1−ヒドロキシシクロヘキシルフェニルケトン、ビス(η5−2,4−シクロペンタジエン−1−イル)−ビス(2,6−ジフルオロ−3−(1H−ピロール−1−イル)−フェニル)チタニウム、ビス(2,4,6−トリメチルベンゾイル)フェニルフォスフィンオキサイド、及び2,4,6−トリメチルベンゾイルジフェニルフォスフィンオキサイドが挙げられる。
本発明の光硬化性接着剤は、形成される接着膜と基板との接着性をさらに向上させる観点から、シランカップリンク剤(E)をさらに含有してもよい。このような観点から、本発明の光硬化性接着剤全量に対するシランカップリンク剤(E)の含有量は、0.01〜20重量%であることが好ましく、0.05〜15重量%であることがより好ましく、0.1〜10重量%であることがさらに好ましい。シランカップリング剤(E)は一種でも二種以上でもよい。
本発明の光硬化性接着剤は、塗布均一性をさらに向上させる観点から、界面活性剤(F)をさらに含有してもよい。このような観点から、本発明の光硬化性接着剤全量に対する界面活性剤(F)の含有量は、0.01〜10重量%であることが好ましく、0.01〜8重量%であることがより好ましく、0.01〜5重量%であることがさらに好ましい。界面活性剤(F)は一種でも二種以上でもよい。
表1及び表2に記載されているA〜Fの各成分を、これらの表に記載されている配合量(重量%)で混合して攪拌することにより光硬化性接着剤を得た。
A−1 ヒドロキシプロピルセルロース(Acros Organics,Hydroxypropyl cellulose, Average M.W. 100,000)
A−2 メチルセルロース(和光純薬工業(株)、メチルセルロース400)
A−3 ヒドロキシエチルセルロース(和光純薬工業(株)、ヒドロキシエチルセルロース)
B−1 酸変性エポキシアクリレート (日本化薬株式会社、製品名:KAYARD ZFR−1491)
B−2 酸変性エポキシアクリレート (日本化薬株式会社、製品名:KAYARD CCR−1285)
B−3 酸変性エポキシアクリレート (日本化薬株式会社、製品名:KAYARD CCR−1287)
B−4 酸変性エポキシアクリレート (日本ユピカ株式会社、製品名:ネオポール 8477−350)
B−5 ジペンタエリスリトールヘキサアクリレート(東亞合成株式会社、製品名:アロニックス M−402)
B−6 2官能アクリレート(共栄社化学株式会社、製品名:エポキシエステル80MFA)
B−7 2官能アクリレート(共栄社化学株式会社、製品名:エポキシエステル70PA)
B−8 2官能アクリレート(共栄社化学株式会社、製品名:エポキシエステル200PA)
B−9 4−ヒドロキシブチルアクリレート(日本化成株式会社、製品名:4−HBA)B−10 2−ヒドロキシエチルメタアクリレート(関東化学株式会社、製品名:HEMA)
B−11 2−ヒドロキシエチルアクリレート(関東化学株式会社、製品名:HEA)
C−1 2,4,6−トリメチルベンゾイル−ジフェニル−フォスフィンオキサイド(BASF社、製品名:DAROCUR TPO)
C−2 2−メチル−1−[4−(メチルチオ)フェニル]−2−モルフォリノプロパン−1−オン(BASF社、製品名:IRGACURE 907)
C−3 1−ヒドロキシ−シクロヘキシル−フェニル−ケトン(BASF社、製品名:IRGACURE 184)
D−1 メチルメタクリレート(60)+ブチルメタクリレート(40)共重合体(Mw:10,000)
D−2 メチルメタクリレート(20)+ブチルメタクリレート(80)共重合体(Mw:10,000)
D−3 ブチルメタクリレート(60)+ヒドロキシエチルメタクリレート(40)共重合体(Mw:15,000)
D−4 メチルメタクリレート(16.5)+ヒドロキシエチルメタクリレート(16.5)+ブチルメタクリレート(67)共重合体(Mw:15,000)
E−1 3−メタクリロキシプロピルトリメトキシシラン(チッソ株式会社、製品名:サイラース、S710)
F−1 界面活性剤(DIC株式会社、製品名:メガファックF−556)
EMD)を用いて25℃ において測定した。粘度の単位はmPa・sである。
光硬化性接着剤の接着性は、1cm×4cmガラス上に50μmビーズスペーサーを散布し、ガラス上に接着剤を約0.05mL滴下し、接着剤が滴下されたガラスの表面に1cm×4cmのガラス又はTACフィルムを、下のガラスに対してT字型を形成するように貼り合わせ、圧着し、紫外線を照射して露光(全線1,000mJ/cm2、高圧水銀灯)してガラスとガラス又はTACフィルムとをT字型に接着し、このT字型の検体において互いに接着されているガラスとガラス又はTACフィルムとを手で剥離し、剥離時の様子によって評価した。評価基準は以下のとおりである。
○:検体を剥離するときに抵抗がある。
△:検体を剥離するときに抵抗ややあり。
×:検体を剥離するときに抵抗なし。
○:残存する光硬化性接着剤を1回〜数回の粘着テープの貼り付け及び剥離で除去できた。
×:残存する光硬化性接着剤を粘着テープの貼り付け及び剥離で除去できない。
セルロース誘導体(A成分)を用いない以外は実施例と同様に、表5に記載されているB〜Fの各成分を、この表に記載されている配合量(重量%)で混合して攪拌することにより比較用光硬化性接着剤を得た。また得られた光硬化性接着剤についても、実施例と同様に、粘度、光透過率、屈折率、接着性、及びリペア性について評価した。評価結果を表5、6に示す。
Claims (6)
- セルロース誘導体(A)におけるRの導入率(Rの導入率=Rの個数/(Rの個数+水酸基の個数))が、13%以上である請求項1に記載の光硬化性接着剤。
- 光硬化性媒体が、重量平均分子量1,000〜100,000の共重合体である充填剤(D)を含む請求項1又は2記載の光硬化性接着剤。
- さらに、シランカップリング剤(E)及び界面活性剤(F)の一方又は両方を含む請求項1〜3のいずれか一項に記載の光硬化性接着剤。
- 二つの光学素子が光硬化性接着剤によって接着されてなる表示素子において、光硬化性
接着剤が、請求項1〜4のいずれか一項に記載の光硬化性接着剤である表示素子。 - 二つの光学素子が、表示パネルと入力素子である、請求項5に記載の表示素子。
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| JP2010265613A JP5793855B2 (ja) | 2010-11-29 | 2010-11-29 | 光硬化性接着剤及び表示素子 |
| TW100139617A TWI487761B (zh) | 2010-11-29 | 2011-10-31 | 光硬化性黏合劑及顯示元件 |
| CN201110341542.1A CN102559070B (zh) | 2010-11-29 | 2011-11-02 | 光硬化性粘合剂及显示元件 |
| KR1020110122677A KR101857503B1 (ko) | 2010-11-29 | 2011-11-23 | 광경화성 접착제 및 표시 소자 |
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| JP5545239B2 (ja) * | 2011-02-21 | 2014-07-09 | Jnc株式会社 | 接着した部材からの光硬化性接着剤の除去方法、及び二部材の接着方法 |
| JP6051662B2 (ja) * | 2012-08-03 | 2016-12-27 | 日立化成株式会社 | 回路接続用接着剤組成物、接着シート、接着剤リール及び回路部材の接続構造体 |
| JP6083715B2 (ja) * | 2012-11-29 | 2017-02-22 | 学校法人 芝浦工業大学 | 接着剤及び積層体、並びにこれらの製造方法 |
| JP2014203335A (ja) * | 2013-04-08 | 2014-10-27 | 日本写真印刷株式会社 | タッチパネル用加飾カバー基材及びその製造方法 |
| JP6024586B2 (ja) * | 2013-04-30 | 2016-11-16 | コニカミノルタ株式会社 | 偏光機能付きガラスおよびそれを備えた液晶表示装置 |
| JP6111879B2 (ja) * | 2013-06-11 | 2017-04-12 | 信越化学工業株式会社 | リグノセルロース由来接着剤及びそれを用いた木質複合材料の製造方法 |
| WO2016136901A1 (ja) * | 2015-02-26 | 2016-09-01 | 日本ゼオン株式会社 | 光学フィルム用転写体、光学フィルム、有機エレクトロルミネッセンス表示装置、及び光学フィルムの製造方法 |
| CN111278937A (zh) * | 2017-11-13 | 2020-06-12 | 日本化药株式会社 | 紫外线固化型粘接剂组合物、其固化物和使用了紫外线固化型粘接剂组合物的光学构件的制造方法 |
| JPWO2019208517A1 (ja) * | 2018-04-23 | 2021-05-20 | 日本化薬株式会社 | 紫外線硬化型の接着剤組成物、その硬化物及び光学部材の製造方法 |
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| US4812495A (en) * | 1987-10-19 | 1989-03-14 | Eastman Kodak Company | Anaerobic adhesive compositions |
| DE4214507A1 (de) * | 1992-05-01 | 1993-11-04 | Minnesota Mining & Mfg | Haftklebstoff mit fuellstoff |
| NZ247942A (en) * | 1992-06-29 | 1994-08-26 | Grace W R & Co | Composition comprising aqueous-processable polymer binder and a non-migrating surface active agent and its use as a slip film in a photo-curable element; manufacture of printing reliefs |
| JPH09137089A (ja) * | 1995-11-17 | 1997-05-27 | Kansai Paint Co Ltd | 近赤外光硬化型パテ組成物 |
| JPH09286930A (ja) * | 1996-04-24 | 1997-11-04 | Showa Highpolymer Co Ltd | 水中での施工が可能な硬化性組成物 |
| US7226719B2 (en) * | 2003-09-08 | 2007-06-05 | General Electric Company | Limited play data storage media and coating formulations thereon |
| JP4199151B2 (ja) * | 2004-03-29 | 2008-12-17 | イビデン株式会社 | プリント配線板用接着剤および接着剤層 |
| KR100927611B1 (ko) * | 2005-01-05 | 2009-11-23 | 삼성에스디아이 주식회사 | 감광성 페이스트 조성물, 이를 이용하여 제조된 pdp전극, 및 이를 포함하는 pdp |
| JP2008101105A (ja) * | 2006-10-19 | 2008-05-01 | Denki Kagaku Kogyo Kk | 硬化性組成物 |
| TW200838967A (en) * | 2007-02-02 | 2008-10-01 | Jsr Corp | Composition for radiation-curable adhesive, composite, and method for producing the composite |
| KR20090080756A (ko) * | 2008-01-22 | 2009-07-27 | 삼성에스디아이 주식회사 | 감광성 페이스트 조성물, 이를 이용하여 제조된 플라즈마디스플레이 패널의 격벽 및 이를 포함하는 플라즈마디스플레이 패널 |
| JP5624908B2 (ja) * | 2010-08-09 | 2014-11-12 | 東京応化工業株式会社 | 接着剤組成物 |
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2011
- 2011-10-31 TW TW100139617A patent/TWI487761B/zh not_active IP Right Cessation
- 2011-11-02 CN CN201110341542.1A patent/CN102559070B/zh not_active Expired - Fee Related
- 2011-11-23 KR KR1020110122677A patent/KR101857503B1/ko not_active Expired - Fee Related
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| Publication number | Publication date |
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| TWI487761B (zh) | 2015-06-11 |
| CN102559070B (zh) | 2014-12-10 |
| JP2012116895A (ja) | 2012-06-21 |
| CN102559070A (zh) | 2012-07-11 |
| KR20120058410A (ko) | 2012-06-07 |
| TW201221603A (en) | 2012-06-01 |
| KR101857503B1 (ko) | 2018-05-14 |
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