JP2011006660A - 紫外線硬化型粘着剤組成物、粘着剤層、粘着シートおよびその製造方法 - Google Patents
紫外線硬化型粘着剤組成物、粘着剤層、粘着シートおよびその製造方法 Download PDFInfo
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- JP2011006660A JP2011006660A JP2010113212A JP2010113212A JP2011006660A JP 2011006660 A JP2011006660 A JP 2011006660A JP 2010113212 A JP2010113212 A JP 2010113212A JP 2010113212 A JP2010113212 A JP 2010113212A JP 2011006660 A JP2011006660 A JP 2011006660A
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- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
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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
- C09J135/00—Adhesives based on homopolymers or 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 another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J135/06—Copolymers with vinyl aromatic monomers
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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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
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- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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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
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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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
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Landscapes
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- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
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- Inorganic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
Abstract
【解決手段】アクリル系モノマーを含有するモノマー成分;ゲルパーミエーションクロマトグラフィーによる重量平均分子量が500以上4000以下の芳香族系低分子ポリマー;および光重合開始剤、を含有し、粘着層とした時のヘイズ値が10%以下であることを特徴とする紫外線硬化型粘着剤組成物。さらに平均粒径20nm以下の金属ナノ粒子を含有する紫外線硬化型粘着剤組成物であることが好ましい。
【選択図】なし
Description
芳香族系低分子ポリマーの重量平均分子量は、GPC(ゲル・パーミエー
ション・クロマトグラフィー)により測定した。サンプルは、試料をテトラヒドロフランに溶解して0.1重量%の溶液とし、これを一晩静置した後、0.45μmのメンブレンフィルターで濾過した濾液を用いた。
・分析装置:東ソー社製、HLC−8120GPC
・カラム:東ソー社製、G3000HXL+2000HXL+G1000HXL
・カラムサイズ;各7.8mmφ×30cm 計90cm
・流量:0.8ml/min
・検出器:示差屈折計(RI)
・カラム温度:40℃
・注入量:100μl
・溶離液:テトラヒドロフラン
・検出器:示差屈折計
・標準試料:ポリスチレン
n−ブチルアクリレート100部、4−ヒドロキシブチルアクリレート1部、光重合開始剤(チバ・ジャパン社製,イルガキュア651)0.05部、光重合開始剤(チバ・ジャパン社製,イルガキュア184)0.4部を混合し、充分に窒素置換した後、高圧水銀ランプ(UVAの照度:0.271W/cm2)を間欠的に5分間照射し、粘調なシロップを得た。このシロップでのモノマーの重合率は12.5%であった。このシロップに、トリメチロールプロパントリアクリレート1.0部、スチレン低分子量ポリマー(SX−85、重量平均分子量Mw=1550、ヤスハラケミカル社製)20部を配合して、均一に混合して紫外線硬化型粘着剤組成物を調整した。当該紫外線硬化型粘着剤組成物を、シリコーン処理を施した、38μmのポリエチレンテレフタレート(PET)フィルム(DIAFOIL MRN38,三菱化学ポリエステルフィルム社製)の片面に硬化後の粘着剤層の厚さが30μmになるように塗工し、空気中の酸素による重合阻害を防止するために、その上から同様のシリコーン処理したPETフィルムを設けた後、フィルムを介して、メタルハライドランプによって紫外線を積算光量15J/cm2で照射した。その後、片面のPETフィルムを剥離した状態で、150℃で3分間加熱処理して、粘着シートを作製した。紫外線照射は、フュージョンUVコンベア(CV−110Q−G,電源VPS−6)にて、Dバルブ、石英フィルターで行い、光量はUVパワーパックのUVA(320−390nm)、UVB(280−320nm)、UVC(250−260nm)、UVV(395−445nm)の積算量で表した。
実施例1において、スチレン低分子量ポリマー(SX−100、Mw=2000、ヤスハラケミカル社製)に代えたこと以外は実施例1と同様にして粘着シートを作製した。
実施例1において、紫外線の照射量を積算光量5J/cm2に代えたこと以外は実施例1と同様にして粘着シートを作製した。
平均粒径7nmのジルコニア分散液(NZD−3JF95−E,住友大阪セメント社製)15部(固形分)と、トルエンに溶解したスチレン低分子量ポリマー(ピコラスチックA75,Mw1320,イーストマンケミカル社製)22.5部(固形分)を混合して、室温(23℃)にて乾燥させて固体成分とした。n−ブチルアクリレート100部、4−ヒドロキシブチルアクリレート1部、トリメチロールプロパントリアクリレート0.5部、上記の固体成分、光重合開始剤(チバ・ジャパン社製,イルガキュア651)0.5部、光重合開始剤(チバ・ジャパン社製,イルガキュア184)0.2部を混合して、紫外線硬化型粘着剤組成物を調製した。当該紫外線硬化型粘着剤組成物を、シリコーン処理を施した、38μmのポリエチレンテレフタレート(PET)フィルム(DIAFOIL MRN38,三菱化学ポリエステルフィルム社製)の片面に硬化後の粘着剤層の厚さが30μmになるように塗工し、その上から同様のPETフィルムを設けた後、フィルムを介して、メタルハライドランプによって紫外線を積算光量105J/cm2で照射した。その後、片面のPETフィルムを剥離した状態で、150℃で3分間加熱処理して、粘着シートを作成した。紫外線照射は、フュージョンUVコンベア(CV−110Q−G,電源VPS−6)にて、Dバルブ、石英フィルターで行い、光量はUVパワーパックのUVA(320−390nm)、UVB(280−320nm)、UVC(250−260nm)、UVV(395−445nm)の積算量で表した。
実施例4において、紫外線の積算光量30J/cm2に代えたこと以外は実施例4と同様にして粘着シートを作製した。
実施例1において、スチレン低分子量ポリマー(Mw=6000)に代えたこと以外は実施例1と同様にして粘着シートを作製した。
実施例4において、スチレン低分子量ポリマーを用いなかったこと以外は実施例4と同様にして粘着シートを作製した。
実施例4において、平均粒径7nmのジルコニア分散液(NZD−3JF95−E,住友大阪セメント社製)の代わりに、平均粒径40nmのジルコニア分散液(NZ110−F1510,住友大阪セメント社製)を用いたこと以外は実施例4と同様にして粘着シートを作製した。
実施例3において、スチレン低分子量ポリマーを用いなかったこと以外は実施例3と同様にして粘着シートを作製した。
実施例および比較例で得た幅10mmの粘着シートサンプルを、厚さ25μmのPETフィルム(ルミラー25−S10,東レ社製)に貼り付け、25℃の雰囲気温度で、村上色彩技術研究所製反射・透過率計HR−100型にて、D−65光を用いてJISK−7136に準じて測定した。
実施例および比較例で得られたサンプルに、25℃の雰囲気で、ナトリウムD線を照射し、アッベ屈折率計(ATAGO社製DR−M2)にて屈折率を測定した。
実施例および比較例で得られたサンプルの粘着剤層面に、厚さ25μmのPETフィルム(ルミラー25−S10,東レ社製)を貼り付け、幅20mm×長さ約100mmに裁断したものから、サンプルにおけるシリコーン処理を施したPETフィルムを剥離してから、厚さ0.5mmの無アルカリガラス板(コーニング社製、1737)に、2kgのロール一往復で貼付け、次いで50℃、0.5MPaで30分間オートクレーブ処理して完全に密着させた後、23℃湿度50%の条件に3時間放置後、剥離角度90°、剥離速度300mm/分で剥離接着を測定した。
Claims (11)
- アクリル系モノマーを含有するモノマー成分;
ゲルパーミエーションクロマトグラフィーによる重量平均分子量が500以上4000以下の芳香族系低分子ポリマー;および
光重合開始剤、を含有し、
粘着層とした時のヘイズ値が10%以下であることを特徴とする紫外線硬化型粘着剤組成物。 - モノマー成分100重量部に対して、
芳香族系低分子ポリマー10〜100重量部;
光重合開始剤0.05〜1.5重量部を含有してなることを特徴とする請求項1記載の紫外線硬化型粘着剤組成物。 - さらに、平均粒径20nm以下の金属ナノ粒子を含有してなることを特徴とする請求項1または2記載の紫外線硬化型粘着剤組成物。
- モノマー成分100重量部に対して、平均粒径20nm以下の前記金属ナノ粒子10〜100重量部を含有してなることを特徴とする請求項3記載の紫外線硬化型粘着剤組成物。
- 金属ナノ粒子の平均粒径が5〜20nmであることを特徴とする請求項3または4記載の紫外線硬化型粘着剤組成物。
- アクリル系モノマーが、
一般式:CH2=C(R1)COOR2(但し、R1は、水素原子またはメチル基、R2は、炭素数4から15のアルキル基を表す)で表されるアルキル(メタ)アクリレートであることを特徴とする請求項1〜5のいずれかに記載の紫外線硬化型粘着剤組成物。 - 請求項1〜6のいずれかに記載の紫外線硬化型粘着剤組成物からなる、ヘイズ値が10%以下であることを特徴とする粘着剤層。
- 支持体の少なくとも片側に、請求項1〜6のいずれかに記載の紫外線硬化型粘着剤組成物を塗工する工程、次いで、塗工された紫外線硬化型粘着剤組成物に紫外線を照射して、当該粘着剤組成物を硬化して粘着剤層を形成する工程、を有することを特徴とする粘着シートの製造方法。
- 紫外線照射を、少なくとも5J/cm2の積算光量で行なうことを特徴とする請求項8記載の粘着シートの製造方法。
- 紫外線硬化型粘着剤組成物は、金属ナノ粒子の分散液と芳香族系低分子ポリマーの溶液を混合して乾燥して得られた固形物を、モノマー成分に溶解して調製したものであることを特徴とする請求項8または9記載の粘着シートの製造方法。
- 請求項8〜10のいずれかに記載の製造方法により得られる粘着シート。
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KR1020117027757A KR20120018171A (ko) | 2009-05-22 | 2010-05-18 | 자외선 경화형 점착제 조성물, 점착제층, 점착 시트 및 그 제조 방법 |
US13/321,364 US20120064336A1 (en) | 2009-05-22 | 2010-05-18 | Ultraviolet-curable adhesive agent composite, adhesive agent layer, adhesive sheet, and manufacturing method therefor |
CN201080022425.2A CN102439103B (zh) | 2009-05-22 | 2010-05-18 | 紫外线固化型粘合剂组合物、粘合剂层、粘合片及其制造方法 |
PCT/JP2010/058355 WO2010134521A1 (ja) | 2009-05-22 | 2010-05-18 | 紫外線硬化型粘着剤組成物、粘着剤層、粘着シートおよびその製造方法 |
EP10777754.2A EP2433992A4 (en) | 2009-05-22 | 2010-05-18 | ULTRAVIOLET-CURABLE ADHESIVE AGENT COMPOSITE, ADHESIVE AGENT LAYER, ADHESIVE SHEET, AND METHOD OF MANUFACTURING THE SAME |
TW099116191A TWI493008B (zh) | 2009-05-22 | 2010-05-20 | An ultraviolet hardening type adhesive composition, an adhesive layer, an adhesive sheet, and a method for manufacturing the same |
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JP2000303040A (ja) * | 1999-02-16 | 2000-10-31 | Toyo Chem Co Ltd | カバーテープ |
JP2001279196A (ja) * | 2000-03-30 | 2001-10-10 | Sliontec Corp | 無基材熱伝導性粘着テープ・シート及びその製造方法 |
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JP2013077633A (ja) * | 2011-09-29 | 2013-04-25 | Lintec Corp | チップ用樹脂膜形成用組成物、チップ用樹脂膜形成用シートおよび半導体装置の製造方法 |
JP2013084684A (ja) * | 2011-10-06 | 2013-05-09 | Lintec Corp | チップ用樹脂膜形成用シートおよび半導体チップの製造方法 |
JP2013216725A (ja) * | 2012-04-04 | 2013-10-24 | Cheil Industries Inc | 粘着剤組成物 |
JP2020537706A (ja) * | 2017-10-20 | 2020-12-24 | エルジー・ケム・リミテッド | インク組成物 |
US11214699B2 (en) | 2017-10-20 | 2022-01-04 | Lg Chem, Ltd. | Ink composition |
JP7118145B2 (ja) | 2017-10-20 | 2022-08-15 | エルジー・ケム・リミテッド | インク組成物 |
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EP2433992A4 (en) | 2015-04-01 |
TW201105761A (en) | 2011-02-16 |
EP2433992A1 (en) | 2012-03-28 |
KR20120018171A (ko) | 2012-02-29 |
TWI493008B (zh) | 2015-07-21 |
US20120064336A1 (en) | 2012-03-15 |
CN102439103A (zh) | 2012-05-02 |
CN102439103B (zh) | 2014-09-03 |
JP5679696B2 (ja) | 2015-03-04 |
WO2010134521A1 (ja) | 2010-11-25 |
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