JP6160887B2 - 粘着剤組成物 - Google Patents
粘着剤組成物 Download PDFInfo
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- JP6160887B2 JP6160887B2 JP2016521205A JP2016521205A JP6160887B2 JP 6160887 B2 JP6160887 B2 JP 6160887B2 JP 2016521205 A JP2016521205 A JP 2016521205A JP 2016521205 A JP2016521205 A JP 2016521205A JP 6160887 B2 JP6160887 B2 JP 6160887B2
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- sensitive adhesive
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- 239000000853 adhesive Substances 0.000 title description 33
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
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- 125000005442 diisocyanate group Chemical group 0.000 description 3
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 3
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- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
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- 101100425892 Danio rerio tpma gene Proteins 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
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- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
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- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- WYOXPIKARMAQFM-UHFFFAOYSA-N n,n,n',n'-tetrakis(oxiran-2-ylmethyl)ethane-1,2-diamine Chemical compound C1OC1CN(CC1OC1)CCN(CC1OC1)CC1CO1 WYOXPIKARMAQFM-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- UOMUPDCRXJLVGR-UHFFFAOYSA-N propane-1,2,2-triol Chemical compound CC(O)(O)CO UOMUPDCRXJLVGR-UHFFFAOYSA-N 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003498 tellurium compounds Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 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 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- 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]
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- C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
-
- 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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
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- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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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
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/10—Homopolymers or copolymers of methacrylic acid esters
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- 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
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- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
- C09J7/22—Plastics; Metallised plastics
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- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
- C09J7/29—Laminated material
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- 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
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- 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
- C09J7/385—Acrylic polymers
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- 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
- C09J7/387—Block-copolymers
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
- G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- 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
- G02F1/01—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
- 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
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133528—Polarisers
-
- 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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- 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
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/062—Copolymers with monomers not covered by C09J133/06
- C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups
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- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
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- C09J2301/00—Additional features of adhesives in the form of films or foils
- 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
- C09J2301/302—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 the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
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- C09J2453/00—Presence of block copolymer
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polarising Elements (AREA)
- Liquid Crystal (AREA)
Description
[化学式1]
(R1)nSi(R2)(4-n)
[化学式2]
(R3)nSi(R2)(4-n)
ゲル分率(%) = B/A × 100
数平均分子量(Mn)および分子量分布(PDI)はGPCを用いて以下の条件で測定し、検量線の製作にはAgilent systemの標準ポリスチレンを用いて測定結果を換算した。
測定機:Agilent GPC(Agilent 1200 series,U.S.)
コラム:PL Mixed B 2個連結
コラム温度:40℃
溶離液:THF(Tetrahydrofuran)
流速:1.0ml/min
濃度:〜 1 mg/ml(100μL injection)
コーティング固形分は次の方法で評価した。
1)アルミニウムディッシュ(aluminum dish)の重さ(A)を測定する。
2)実施例または比較例の粘着剤組成物を0.3g〜0.5g程度の量(乾燥前試料)で採取して前記アルミニウムディッシュに入れる。
3)エチルアセテートに溶解された重合禁止剤(hydroquinone)溶液(濃度:0.5重量%)をピペット(pipette)で極少量粘着剤組成物に添加する。
4)150℃のオーブンで30分程度乾燥させて溶媒などを除去する。
5)常温で15分〜30分程度冷ました後、残留成分の重さ(乾燥後試料の重さ)を測定する。
6)前記測定結果にしたがって下記の数式でコーティング固形分を評価する。
コーティング固形分(単位:%) = 100 ×(DS- A)/(S+E)
DS:アルミニウムディッシュの重さ(A) + 乾燥後試料の重さ(単位:g)
A:アルミニウムディッシュの重さ(単位:g)
S:乾燥前試料の重さ(単位:g)
E:除去された成分(溶媒など)の重さ(単位:g)
粘着剤組成物の粘度は測定機(Brookfield digital viscometer(DV-I+、DV-II+Pro))を用いて下記の方式で評価した。
1)ビーカーに粘着剤組成物(サンプル)を180mlを入れ、恒温/恒湿(23℃/50%相対湿度)条件で1時間程度放置して気泡を除去する。
2)粘着剤組成物(サンプル)の液面がスピンドル(spindle)の溝より深く当たらないようにしてサンプルにスピンドルを気泡が発生しないように斜めに入れる。
3)スピンドルを粘度計に連結して、サンプルの液面がスピンドルの溝に合うように調節する。
4)セットスピードキー(set speed key)を押してスピンドルのRPMを選択する。
5)モーターオン/オフキー(motor on/off key)を押して粘度計を作動させる。画面に示された粘度数値が安定化するまで待機して値を得る。ディスプレイ上にて信頼区間が約10%以上となるRPMを探してRPMを固定させ、粘度を測定する。
実施例および比較例で製造された粘着剤組成物をコーティングし、コーティング層を目視で観察して下記の基準で評価する。
A:コーティング層に気泡および縞模様などが目視によって確認されない
B:コーティング層に気泡および/または縞模様などが目視で微細に観察される
C:コーティング層に気泡および/または縞模様が目視で顕著に観察される
実施例および比較例で製造した偏光板を幅が180 mm程度、長さが320 mm程度となるように裁断して試片を製造し、これを19インチ市販のパネルに付着する。その後、パネルをオートクレーブ(50℃、5気圧)で約20分の間保管してサンプルを製造する。製造されたサンプルの耐熱耐久性はサンプルを80℃で500時間の間維持した後で同じく気泡および剥離の発生を観察して下記の基準で評価し、耐湿熱耐久性はサンプルを60℃および90%相対湿度条件で500時間放置した後で粘着界面での気泡および剥離の発生を観察して下記の基準によって評価した。
A:気泡および剥離発生なし
B:気泡および/または剥離若干発生
C:気泡および/または剥離多量発生
実施例および比較例で製造した偏光板を幅が180 mm程度、長さが320 mm程度となるように裁断して試片を製造し、これを19インチ市販のパネルに付着する。その後、パネルをオートクレーブ(50℃、5気圧)で約20分の間保管してサンプルを製造する。製造されたサンプルの耐湿熱以後常温低湿耐久性はサンプルを60℃および90%相対湿度条件で500時間放置した後で粘着界面での気泡および剥離の発生を観察して下記の基準で評価した後、A評価基準を満足させるサンプルに対して25℃および25%相対湿度条件で500時間放置した後で下記の基準によって再評価した。
A:気泡および剥離発生なし
B:気泡および/または剥離若干発生
C:気泡および/または剥離多量発生
ブロック共重合体の各ブロックなどのガラス転移温度(Tg)は下記の数式にしたがって算出した。
1/Tg = Σn/Tn
実施例および比較例のブロック共重合体で第1ブロックを形成する主要単量体であるメチルメタクリレート(mmA)と第2ブロックを形成する主要単量体であるブチルアクリレート(BA)の重合過程での転換率およびブロック共重合体内での組成含量は1H-NMRの結果にしたがって以下の数式で算出した。
mmA転換率(%) = 100 × B/(A+B)
BA転換率(%) = 100 × C/(C+D)
ブロック共重合体の第1および第2ブロックの比率は、第1ブロックおよび第2ブロックを形成することに用いた主要単量体であるメチルメタクリレート(mmA)およびブチルアクリレート(BA)の比率に基づいて下記の数式に基づいて算定した。
ブロック共重合体内のmmAの含量(%) = 100 × mmAピーク面積/BAピーク面積
実施例および比較例で製造された粘着剤組成物を乾燥後の厚さが40μm程度となるように離型処理された厚さ38μmの離型PET(poly(ethyleneterephthalate))(MRF-38、三菱製)の離型処理面にコーティングし、110℃のオーブンで約3分の間維持した後、コーティングされた粘着剤層の透明度を目視で観察して下記の基準で評価した。
A:コーティング層が非常に透明
B:コーティング層が若干透明であるか不透明または非常に不透明
EBiB(ethyl2-bromoisobutyrate)0.1gおよびメチルメタクリレ−ト(mmA)14.2gをエチルアセテート(EAc)6.2gに混合した。前記混合物が入れられたフラスコをゴム膜で密封し、約25℃で約30分の間窒素パージングおよび撹拌し、バブリングを通じて溶存酸素を除去した。その後、CuBr20.002g、TPMA(tris(2-pyridylmethyl)amine)0.005gおよびV-65(2、2'-azobis(2、4-dimethyl valeronitrile))0.017gを酸素が除去された前記混合物に投入し、約67℃の反応槽に漬けて反応を開始させた(第1ブロックの重合)。メチルメタクリレ−トの転換率が約75%程度の時点で、あらかじめ窒素でバブルリングしておいたブチルアクリレート(BA)115g、ヒドロキシブチルアクリレート(HBA)0.8gおよびエチルアセテート(EAc)250gの混合物を窒素の存在下で投入した。その後、反応フラスコにCuBr20.006g、TPMA0.01gおよびV-65 0.05gを入れて、鎖延長反応(chain extention reaction)を遂行した(第2ブロックの重合)。単量体(BA)の転換率が80%以上に到達すると前記反応混合物を酸素に露出させ、適切な溶媒に希釈して反応を終結させることによってブロック共重合体を製造した(前記過程でV-65は、その半減期を考慮して反応終了時点まで適切に分割して投入した)。
第1ブロックの重合時に用いられた原料および添加剤などの種類を下記の表1のように調節し、第2ブロックの重合時に用いられた原料および添加剤などの種類を下記の表2のように調節したことを除いては製造例1の場合と同一にブロック共重合体を製造した。
窒素ガスが還流され、温度調節が容易となるよう冷却装置を設置した1L反応器にメチルメタクリレ−ト(mmA)10重量部、n-ブチルアクリレート87.3重量部およびヒドロキシブチルアクリレート(HBA)2.7重量部を投入し、分子量調節剤としてn-ドデシルメルカプタンを200ppmの量で添加した後、溶剤としてエチルアセテート120重量部を投入した。引き続き、酸素除去のために窒素ガスを約60分間パージし、温度を60℃で維持した状態で反応開始剤であるAIBN(azobisisobutyronitrile)0.05重量部を投入し、約8時間の間反応させてランダム共重合体を製造した。製造されたランダム共重合体(C1)の数平均分子量(Mn)は約132000であり、分子量分布(PDI)は約4.6であった。
窒素ガスが還流され、温度調節が容易となるよう冷却装置を設置した1L反応器にブチルアクリレート(BA)98重量部およびヒドロキシブチルアクリレート(HBA)2重量部を投入し、分子量調節剤としてn-ドデシルメルカプタンを350ppmの量で添加した後、溶剤としてエチルアセテート120重量部を投入した。引き続き、酸素除去のために窒素ガスを約60分間パージし、温度を60℃で維持した状態で反応開始剤であるAIBN(azobisisobutyronitrile)0.03重量部を投入し、約8時間の間反応させてランダム共重合体を製造した。製造されたランダム共重合体(C2)の数平均分子量(Mn)は約310000であり、分子量分布(PDI)は約3.3であった。
窒素ガスが還流され、温度調節が容易となるよう冷却装置を設置した1L反応器にブチルアクリレート(BA)98重量部およびヒドロキシブチルアクリレート(HBA)2重量部を投入し、分子量調節剤としてn-ドデシルメルカプタンを600ppmの量で添加した後、溶剤としてエチルアセテート120重量部を投入した。引き続き、酸素除去のために窒素ガスを約60分間パージし、温度を60℃で維持した状態で反応開始剤であるAIBN(azobisisobutyronitrile)0.03重量部を投入し、約8時間の間反応させてランダム共重合体を製造した。製造されたランダム共重合体(C3)の数平均分子量(Mn)は約178000であり、分子量分布(PDI)は約2.8であった。
コーティング液(粘着剤組成物)の製造
製造例1で製造されたブロック共重合体(A1)100重量部に対して製造例9で製造したランダム共重合体(C2)15重量部、架橋剤(Coronate L、日本NPU製)0.04重量部、DBTDL(Dibutyltin dilaurate)0.1重量部およびβシアノアセチル基を有するシランカップリング剤0.2重量部を混合し、溶剤としてエチルアセテートを配合してコーティング固形分が約31重量%になるように調節してコーティング液(粘着剤組成物)を製造した。
製造されたコーティング液を乾燥後の厚さが約23μm程度となるように離型処理された厚さ38μmの離型PET(poly(ethylene terephthalate))(MRF-38、三菱製)の離型処理面にコーティングし、110℃のオーブンで約3分の間維持した。乾燥後で片面にWV(Wide View)液晶層がコーティングされた偏光板(TAC/PVA/TACの積層構造:TAC=トリアセチルセルロース、PVA=ポリビニルアルコール系偏光フィルム)のWV液晶層に前記離型PET上に形成されたコーティング層をラミネートして粘着偏光板を製造した。
粘着剤組成物(コーティング液)の製造時に各成分および比率を下記の表4のように調節したのを除いては実施例1と同一に粘着剤組成物(コーティング液)および粘着偏光板を製造した。ただし、比較例8の場合、製造例8で製造されたランダム共重合体(C1)100重量部に対して各成分および比率を表4のように調節して粘着剤組成物(コーティング液)および粘着偏光板を製造した。
Claims (14)
- ガラス転移温度が50℃以上である第1ブロックとガラス転移温度が-10℃以下である第2ブロックを含むブロック共重合体;
架橋性官能基を有するアクリル共重合体;および
多官能性架橋剤を含み、
ブロック共重合体の第1ブロックは(メタ)アクリル酸エステル単量体から誘導された重合単位を含み、
ブロック共重合体の第2ブロックは(メタ)アクリル酸エステル単量体90〜99.9重量部および架橋性官能基を有する共重合性単量体0.1〜10重量部から誘導された重合単位を含み、
アクリル共重合体は、数平均分子量が20万以上であり、ブロック共重合体100重量部対比5重量部〜50重量部で含まれる、粘着剤組成物。 - ブロック共重合体の第1ブロック5重量部〜50重量部および第2ブロック50重量部〜95重量部を含む、請求項1に記載の粘着剤組成物。
- ブロック共重合体は分子量分布が1.0〜2.5である、請求項1に記載の粘着剤組成物。
- アクリル共重合体は(メタ)アクリル酸エステル単量体90重量部〜99.9重量部および架橋性官能基を有する共重合性単量体0.1重量部〜10重量部から由来した重合単位を含む、請求項1に記載の粘着剤組成物。
- アクリル共重合体の架橋性官能基とブロック共重合体の架橋性官能基は同一の官能基である、請求項1に記載の粘着剤組成物。
- 架橋性官能基はヒドロキシ基である、請求項5に記載の粘着剤組成物。
- アクリル共重合体は分子量分布が2.0〜4.5である、請求項1に記載の粘着剤組成物。
- 多官能性架橋剤はブロック共重合体100重量部対比0.01重量部〜10重量部で含まれる、請求項1に記載の粘着剤組成物。
- コーティング固形分が20重量%以上である、請求項1に記載の粘着剤組成物。
- 23℃でコーティング粘度が500cP〜3,000cPである、請求項1に記載の粘着剤組成物。
- 架橋構造を具現した後の下記の一般式1によるゲル分率が80重量%以下である、請求項1に記載の粘着剤組成物:
[一般式1]
ゲル分率(%)= B/A × 100 一般式1で、Aは架橋構造を具現している前記粘着剤組成物の質量であり、Bは、前記質量Aの粘着剤組成物を200メッシュ(mesh)の大きさの網に入れた状態で常温でエチルアセテートに72時間沈積させた後で採取した不溶解分の乾燥質量を現わす。 - 光学フィルム;および前記光学フィルムの一面または両面に形成されており、架橋された請求項1に記載された粘着剤組成物を含む粘着剤層を有する、粘着型光学部材。
- 偏光子;および前記偏光子の一面または両面に形成されており、架橋された請求項1に記載された粘着剤組成物を含む粘着剤層を有する、粘着型偏光板。
- 請求項12に記載された光学部材または請求項13に記載された偏光板を含む、ディスプレイ装置。
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