JP2010090249A - 紫外線硬化型再剥離性粘着剤組成物及びこれを用いた粘着シート - Google Patents
紫外線硬化型再剥離性粘着剤組成物及びこれを用いた粘着シート Download PDFInfo
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- JP2010090249A JP2010090249A JP2008261055A JP2008261055A JP2010090249A JP 2010090249 A JP2010090249 A JP 2010090249A JP 2008261055 A JP2008261055 A JP 2008261055A JP 2008261055 A JP2008261055 A JP 2008261055A JP 2010090249 A JP2010090249 A JP 2010090249A
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- hydrogen atom
- sensitive adhesive
- ethylenically unsaturated
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- 239000000853 adhesive Substances 0.000 title abstract description 47
- 230000001070 adhesive effect Effects 0.000 title abstract description 47
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- 229920000642 polymer Polymers 0.000 claims abstract description 26
- 239000003522 acrylic cement Substances 0.000 claims abstract description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 20
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 14
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
- 230000009257 reactivity Effects 0.000 claims abstract description 6
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 50
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 27
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- 239000003999 initiator Substances 0.000 claims description 11
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
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- VPASWAQPISSKJP-UHFFFAOYSA-N ethyl prop-2-enoate;isocyanic acid Chemical compound N=C=O.CCOC(=O)C=C VPASWAQPISSKJP-UHFFFAOYSA-N 0.000 description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 4
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 4
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
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- 238000012545 processing Methods 0.000 description 3
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- QASBHTCRFDZQAM-UHFFFAOYSA-N (2-isocyanato-2-methyl-3-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(C)(COC(=O)C=C)N=C=O QASBHTCRFDZQAM-UHFFFAOYSA-N 0.000 description 2
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
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- C09J133/00—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/54—Polycondensates of aldehydes
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/6254—Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy groups
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/68—Unsaturated polyesters
- C08G18/683—Unsaturated polyesters containing cyclic groups
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/81—Unsaturated isocyanates or isothiocyanates
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- C08G18/815—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen
- C08G18/8158—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen
- C08G18/8175—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen
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- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
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- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
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Abstract
ウエハなどの集積回路形成に有用な成膜性のある紫外線硬化型粘着剤として、ダイシングテープに有用な硬化前後における粘着膜の強度の低減が好ましい範囲で、保持力が高く、硬化膜を剥離した際に、ウエハ表面に糊残りのない硬化膜を与える紫外線硬化型再剥離性粘着剤を提供する。
【解決手段】
本発明は、(a)アクリル系粘着性ポリマー、(b)多官能エポキシアクリレート、(c)光重合開始剤、(d)水酸基、カルボキシル基又はエポキシ基に対して反応性を有する硬化剤からなる紫外線硬化型再剥離性粘着剤に関する。また、本発明は、前記紫外線硬化型再剥離性粘着剤組成物を用いた粘着シートに関する。
【選択図】 なし
Description
(式中、R8は水素原子又はメチル基であり、R9は水素原子又はエチレン性不飽和結合を有する基である)で表される基、又は式(5):
○:きれいな状態の粘着層。
△:ハジキやブツブツが少し見られる。
×:ハジキやブツブツがはっきりと見られる。
○:被着体に粘着剤が残らない。
△:被着体に粘着剤が僅かに残る。
×:被着体に粘着剤がはっきりと残る。
攪拌機、温度調節器、還流冷却器、滴下ロート、温度計を付した反応装置に、アクリル酸n−ブチル80部、アクリル酸エチル60部、メタクリル酸メチル6.3部、アクリル酸1部、アクリル酸2−ヒドロキシエチル0.8部及び酢酸エチル130部を仕込み、加熱還流開始後、重合開始剤としてアゾビスイソブチロニトリル0.1部を加え、酢酸エチル還流温度で3時間反応後、アゾビスイソブチロニトリル0.1部をトルエン4部に溶解させたものを加え、還流温度にて更に4時間反応させ、トルエンにて希釈することにより樹脂分40%、重量平均分子量55万、ガラス転移温度−35.2℃のアクリル系粘着剤(1)を得た。尚、重量平均分子量はゲルパーミションクロマトグラフィー法で、ガラス転移温度は示差走査熱量計(DSC)によって求めた。
攪拌機、温度調節器、還流冷却器、滴下ロート、温度計を付した反応装置に、アクリル酸n−ブチル80部、アクリル酸メチル60部、メタクリル酸メチル6.3部、アクリル酸1部、アクリル酸2−ヒドロキシエチル0.8部及び酢酸エチル130部を仕込み、加熱還流開始後、重合開始剤としてアゾビスイソブチロニトリル0.2部を加え、酢酸エチル還流温度で8時間反応後、トルエンにて希釈することにより樹脂分40%、重量平均分子量61万、ガラス転移温度−25.3℃のアクリル系粘着剤(2)を得た。
攪拌機、温度調節器、還流冷却器、滴下ロート、温度計を付した反応装置に、ビスフェノールA型エポキシ樹脂(旭化成エポキシ株式会社製、商品名アラルダイトAER2603 、エポキシ当量189)100部(1.0当量)、アクリル酸37部(1.0モル)、トリフェニルフォスフィン0.6部、メチルハイドロキノン0.12部を仕込み、空気を吹き込みながら、120℃で8時間反応を続け、酸価0.5KOHmg/gの反応物を得た。次に温度を60℃まで下げ、滴下ロートを通じてイソシアナートエチルメタクリレート(昭和電工株式会社製、商品名カレンズMOI)62部とジブチル錫ジラウレート0.02部の混合液を滴下し、滴下終了後反応系を70℃で4時間保持することにより、イソシアナート基を消失させ、重量平均分子量1300の多官能エポキシアクリレート(1)を得た。
攪拌機、温度調節器、還流冷却器、滴下ロート、温度計を付した反応装置に、クレゾールノボラック型エポキシ樹脂(東都化成株式会社製、商品名YD−704L 、エポキシ当量209)100部(1.0当量)、アクリル酸33部(1.0モル)、トリフェニルフォスフィン0.4部、メチルハイドロキノン0.08部を仕込み、空気を吹き込みながら、120℃で8時間反応を続け、酸価0.5KOHmg/gの反応物を得た。次に温度を60℃まで下げ、滴下ロートを通じてイソシアナートエチルメタクリレート(昭和電工株式会社製、商品名カレンズMOI)56部とジブチル錫ジラウレート0.02部の混合液を滴下し、滴下終了後反応系を70℃で4時間保持することにより、イソシアナート基を消失させ、重量平均分子量4000の多官能エポキシアクリレート(2)を得た。
攪拌機、温度調節器、還流冷却器、滴下ロート、温度計を付した反応装置に、トリアジン核を骨格にもつ3価のエポキシ化合物(日産化学工業株式会社製、商品名TEPIC−S 、エポキシ当量100)100部(1.0当量)、アクリル酸72部(1.0モル)、トリフェニルフォスフィン0.6部、メチルハイドロキノン0.12部を仕込み、空気を吹き込みながら、120℃で8時間反応を続け、酸価0.5KOHmg/gの反応物を得た。次に温度を60℃まで下げ、滴下ロートを通じてイソシアナートエチルメタクリレート(昭和電工株式会社製、商品名カレンズMOI)70部とジブチル錫ジラウレート0.02部の混合液を滴下し、滴下終了後反応系を70℃で4時間保持することにより、イソシアナート基を消失させ、重量平均分子量1100の多官能エポキシアクリレート(3)を得た。
紫外線の遮断された室内にて、プラスチック製容器に、アクリル系粘着剤(1)70部、多官能エポキシアクリレート(1)30部、1−ヒドロキシ-シクロヘキシル−フェニル−ケトン(チバ・スペシャルティ・ケミカルズ社製、イルガキュア184)1.2部、トリメチロールプロパンのトリレンジイソシアネート付加物の45%酢酸エチル溶液(日本ポリウレタン工業株式会社製、コロネートL−45E)2.0部を加えて攪拌し、再剥離性粘着剤とし、さらにこれを厚さ50μmのポリエチレンテレフタレートフィルムに乾燥後の膜厚が20μmになるように塗工し、105℃で2分間、加熱乾燥させて再剥離型粘着シートを作製した。次に、前述の方法で紫外線硬化前後の性能変化を評価した。測定結果を表1に示す。
実施例1の再剥離型粘着シートの製造において、アクリル系粘着剤(1)の使用量を60部、多官能エポキシアクリレート(1)の使用量を40部に変更した他は実施例1と同様の方法で再剥離型粘着シートを製造し、紫外線硬化前後の性能変化を評価した。測定結果を表1に示す。
実施例1の再剥離型粘着シートの製造において、アクリル系粘着剤(1)の使用量を50部、多官能エポキシアクリレート(1)の使用量を50部に変更した他は実施例1と同様の方法で再剥離型粘着シートを製造し、紫外線硬化前後の性能変化を評価した。測定結果を表1に示す。
実施例1の再剥離型粘着シートの製造において、アクリル系粘着剤(2)の使用量を60部、多官能エポキシアクリレート(1)の使用量を40部に変更した他は実施例1と同様の方法で再剥離型粘着シートを製造し、紫外線硬化前後の性能変化を評価した。測定結果を表1に示す。
実施例1の再剥離型粘着シートの製造において、アクリル系粘着剤(2)の使用量を50部、多官能エポキシアクリレート(1)の使用量を50部に変更した他は実施例1と同様の方法で再剥離型粘着シートを製造し、紫外線硬化前後の性能変化を評価した。測定結果を表1に示す。
実施例1の再剥離型粘着シートの製造において、アクリル系粘着剤(1)の使用量を70部、多官能エポキシアクリレート(2)の使用量を30部に変更した他は実施例1と同様の方法で再剥離型粘着シートを製造し、紫外線硬化前後の性能変化を評価した。測定結果を表1に示す。
実施例1の再剥離型粘着シートの製造において、アクリル系粘着剤(1)の使用量を70部、多官能エポキシアクリレート(3)の使用量を30部に変更した他は実施例1と同様の方法で再剥離型粘着シートを製造し、紫外線硬化前後の性能変化を評価した。測定結果を表1に示す。
実施例1の再剥離型粘着シートの製造において、多官能エポキシアクリレート(1)をビスフェノールA型エポキシアクリレート(昭和高分子株式会社製、商品名VR−77)に変更した他は実施例1と同様の方法で再剥離型粘着シートを製造し、紫外線硬化前後の性能変化を評価した。測定結果を表2に示す。
実施例1の再剥離型粘着シートの製造において、アクリル系粘着剤(1)の使用量を60部とし、多官能エポキシアクリレート(1)の代わりにビスフェノールA型エポキシアクリレート40部とした他は実施例1と同様の方法で再剥離型粘着シートを製造し、紫外線硬化前後の性能変化を評価した。測定結果を表2に示す。
実施例1の再剥離型粘着シートの製造において、アクリル系粘着剤(1)の使用量を70部とし、多官能エポキシアクリレート(1)の代わりにジペンタエリスリトールヘキサアクリレート(日本化薬株式会社製、商品名KAYARAD DPHA)30部に変更した他は実施例1と同様の方法で再剥離型粘着シートを製造し、紫外線硬化前後の性能変化を評価した。測定結果を表2に示す。
実施例1の再剥離型粘着シートの製造において、アクリル系粘着剤(1)の使用量を60部とし、多官能エポキシアクリレート(1)の代わりにビスフェノールA型エポキシアクリレート20部、及びジペンタエリスリトールヘキサアクリレート20部に変更した他は実施例1と同様の方法で再剥離型粘着シートを製造し、紫外線硬化前後の性能変化を評価した。測定結果を表2に示す。
Claims (7)
- (a)アクリル系粘着性ポリマー、(b)多官能エポキシアクリレート、(c)光重合開始剤、(d)水酸基、カルボキシル基又はエポキシ基に対して反応性を有する硬化剤からなり、(b)多官能エポキシアクリレートが式(1):
- アクリル系粘着性ポリマー(a)100質量部に対して、多官能エポキシアクリレート(b)20〜200質量部からなる請求項1、2又は3のいずれかに記載の紫外線硬化型再剥離性粘着剤組成物。
- アクリル系粘着性ポリマー(a)が、重量平均分子量20万〜200万で、ガラス転移温度が−50℃〜10℃であり、且つ水酸基を有する(メタ)アクリル酸エステル共重合体からなる請求項1、2、3又は4のいずれかに記載の紫外線硬化型再剥離性粘着剤組成物。
- 多官能エポキシアクリレート(b)は、エポキシアクリレートとα,β−エチレン性不飽和モノイソシアナートとの反応性生成物であることを特徴とする請求項1、2、3、4又は5のいずれかに記載の紫外線硬化型再剥離性粘着剤組成物。
- 請求項1、2、3、4、5又は6のいずれかに記載の紫外線硬化型再剥離性粘着剤組成物を用いた粘着シート。
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JP2014234422A (ja) * | 2013-05-31 | 2014-12-15 | 昭和電工株式会社 | ガラスエッチング向け再剥離保護テープ用活性線硬化型粘着剤組成物、ガラスエッチング向け再剥離保護テープ |
JP2015147828A (ja) * | 2014-02-05 | 2015-08-20 | 大日本印刷株式会社 | 粘着剤組成物およびそれを用いた粘着フィルム |
JP2017156152A (ja) * | 2016-02-29 | 2017-09-07 | リンテック株式会社 | 証拠採取方法、証拠採取用シート、証拠採取用シートの製造方法 |
JP2019019150A (ja) * | 2017-07-11 | 2019-02-07 | 昭和電工株式会社 | 粘着剤組成物および粘着シート |
CN108841345A (zh) * | 2018-07-09 | 2018-11-20 | 烟台德邦科技有限公司 | 一种混杂固化光致变黑丙烯酸酯胶黏剂 |
WO2020049829A1 (ja) * | 2018-09-03 | 2020-03-12 | 昭和電工株式会社 | 粘着剤組成物および粘着シート |
KR20210027424A (ko) * | 2018-09-03 | 2021-03-10 | 쇼와 덴코 가부시키가이샤 | 점착제 조성물 및 점착 시트 |
JPWO2020049829A1 (ja) * | 2018-09-03 | 2021-08-12 | 昭和電工株式会社 | 粘着剤組成物および粘着シート |
KR102408062B1 (ko) | 2018-09-03 | 2022-06-14 | 쇼와 덴코 가부시키가이샤 | 점착제 조성물 및 점착 시트 |
JP7363791B2 (ja) | 2018-09-03 | 2023-10-18 | 株式会社レゾナック | 粘着剤組成物および粘着シート |
JPWO2020116101A1 (ja) * | 2018-12-07 | 2021-10-21 | 昭和電工株式会社 | 粘着剤組成物および粘着シート |
JP7396297B2 (ja) | 2018-12-07 | 2023-12-12 | 株式会社レゾナック | 粘着剤組成物および粘着シート |
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CN102177214B (zh) | 2013-09-25 |
KR101547378B1 (ko) | 2015-08-25 |
TW201014892A (en) | 2010-04-16 |
CN102177214A (zh) | 2011-09-07 |
KR20110067119A (ko) | 2011-06-21 |
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