JP6134000B2 - 粘着剤組成物 - Google Patents
粘着剤組成物 Download PDFInfo
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- JP6134000B2 JP6134000B2 JP2015542983A JP2015542983A JP6134000B2 JP 6134000 B2 JP6134000 B2 JP 6134000B2 JP 2015542983 A JP2015542983 A JP 2015542983A JP 2015542983 A JP2015542983 A JP 2015542983A JP 6134000 B2 JP6134000 B2 JP 6134000B2
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- sensitive adhesive
- pressure
- adhesive composition
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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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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-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
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002905 metal composite material Substances 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- 125000004430 oxygen atom Chemical group O* 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
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000001556 precipitation Methods 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003498 tellurium compounds Chemical class 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
- 238000012546 transfer Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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
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- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
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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
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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
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- 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
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/105—Esters; Ether-esters of monocarboxylic acids with phenols
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- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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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- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
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- G—PHYSICS
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- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- G—PHYSICS
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- 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
- G02B5/3041—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 comprising multiple thin layers, e.g. multilayer stacks
- G02B5/305—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 comprising multiple thin layers, e.g. multilayer stacks including organic materials, e.g. polymeric layers
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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
- 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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- G—PHYSICS
- G02—OPTICS
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- 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
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- 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
- G02F2202/00—Materials and properties
- G02F2202/28—Adhesive materials or arrangements
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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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
- Y10T428/2848—Three or more layers
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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
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- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
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Landscapes
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- Polymers & Plastics (AREA)
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- Adhesive Tapes (AREA)
Description
粘度変化率 = 100 × (Vl − Vo)/Vo
(R1)nSi(R2)(4−n)
(R3)nSi(R2)(4−n)
数平均分子量(Mn)及び分子量分布(PDI)は、GPCを使用して以下の条件で測定した。検量線の製作には、Agilent systemの標準ポリスチレンを使用して測定結果を換算した。
測定器:Agilent GPC(Agilent 1200 series、米国)
カラム:PL Mixed B 2個連結
カラム温度:40℃
溶離液:THF(Tetrahydrofuran)
流速:1.0mL/min
濃度:〜1mg/mL(100μL injection)
粘度は、測定器(Brookfield digital viscometer(DV−I+、DV−II+Pro))を使用して下記方式で評価した。
1)ビーカーにサンプル180mLを入れて、恒温/恒湿(23℃/50%の相対湿度)条件で、1時間程度放置して気泡を除去する。
2)サンプルの液面がスピンドル(spindle)の溝より深く触れないようにしてサンプルにスピンドルを気泡が生じ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、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。画面に現われた粘度数値が安定化するまで待機して値を得る。ディスプレイ上で信頼区間が約10%以上になるRPMを探してRPMを固定して、粘度を測定する。
実施例及び比較例で製造した偏光板を、幅が180mm程度であり、長さが320mm程度になるように裁断して試片を製造し、これを19インチの市販パネルに付着する。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耐久性は、サンプルを60℃及び90%の相対湿度条件で、500時間放置した後に、粘着界面での気泡及び剥離の発生を観察して、下記基準によって評価した。耐熱耐久性は、サンプルを90℃で300時間の間維持した後、同様に気泡及び剥離の発生を観察して、下記基準によって評価した。
A:気泡及び剥離発生なし
B:気泡及び/または剥離多少発生
C:気泡及び/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、下記数式によって算出した。
1/Tg = ΣWn/Tn
実施例及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及びブロック共重合体内での組成含量は、1H−NMRの結果によって以下数式で算出した。
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及び第2ブロックの割合は、第1ブロック及び第2ブロックを形成することに使用した主要単量体であるメチルメタクリレート(MMA)及びブチルアクリレート(BA)の割合に根拠して、下記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
実施例及び比較例で製造した偏光板を、幅が240mmであり、長さが410mmになるように裁断して試片を製造し、市販のガラス基板(0.4t glass)に付着して積層体を製造する。その後、製造された積層体を平たい底に位置させて、60℃で72時間の間放置した後、前記積層体が底から浮き上がった程度の高さを測定して曲がり程度を評価した。
第1ブロックを形成する単量体としてメチルメタクリレート(MMA)及びブチルメタクリレート(BMA)を7:3(MMA:BMA)の重量割合で含む単量体の混合物を、適正量のEBiB(ethyl 2−bromoisobutyrate)及びエチルアセテート(EAc)と混合した。前記混合物が入っているフラスコをゴム膜で密封し、約25℃で約30分間窒素パージング及び撹拌し、バブリングを通じて溶存酸素を除去した。その後、CuBr2、TPMA(tris(2−pyridylmethyl)amine)及びV−65(2,2'−azobis(2,4−dimethyl valeronitrile))の適正量を酸素が除去された前記混合物に投入し、約67℃の反応槽に浸して反応を開始させた(第1ブロックの重合)。メチルメタクリレートの転換率が約75%程度である時点で、予め窒素にバブリングしておいた第2ブロックを形成する混合物を窒素の存在下で投入した。第2ブロックを形成する混合物は、単量体混合物としてブチルアクリレート(BA)及びヒドロキシブチルアクリレート(HBA)を99.5:0.5(BA:HBA)の重量割合で溶媒であるエチルアセテート(EAc)に溶解させて製造した。その後、反応フラスコにCuBr2、TPMA及びV−65の適正量を追加で入れて、鎖延長反応(chain extension reaction)を実行した(第2ブロックの重合)。単量体(BA)の転換率が80%以上に到逹すれば、前記反応混合物を酸素に露出させて、適切な溶媒に希釈して反応を終決させることで、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及び第2ブロックの重合時に使用された単量体及びその割合を下記表1のように調節したこと以外は、製造例1の場合と同一にブロック共重合体を製造した。ブロック共重合体の製造時に、触媒、溶媒または開始剤などに該当するEbiB、EA、CuBr2、TPMA及びV−65などは、重合効率などを考慮して適正量で投入した。
窒素ガスが還流されて、温度調節が容易に冷却装置を設置した1L反応器にメチルメタクリレート(MMA)10重量部、n−ブチルアクリレート87.3重量部及び4−ヒドロキシブチルアクリレート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。その後、酸素の除去のために窒素ガスを約60分間パージングし、温度を60℃に維持した状態で、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(B4)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。
コーティング液(粘着剤組成物)の製造
製造例1で製造したブロック共重合体(A1)100重量部に対して、架橋剤(Coronate L、日本NPU社製)0.1重量部、DBTDL(Dibutyltin dilaurate)0.1重量部及びフェノール系酸化防止剤(Irganox1010、Ciba)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液(粘着剤組成物)を製造した。
製造したコーティング液を乾燥後の厚さが約23μm程度になるように離型処理された厚さ38μmの離型PET(poly(ethylene terephthalate))(MRF−38、三菱社製)の離型処理面にコーティングし、110℃のオーブンで約3分間維持した。乾燥後に片面に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)の製造時に各成分及び割合を下記表3または表4のように調節したこと以外は、実施例1と同一に粘着剤組成物(コーティング液)及び粘着偏光板を製造した。
Claims (15)
- ガラス転移温度が60℃以上であり、架橋性官能基を含まない、アルキルメタクリレートの重合単位を含む第1ブロック及びガラス転移温度が−30℃以下であり、架橋性官能基を含む第2ブロックからなるジブロック共重合体;及び
酸化防止剤または光安定剤を含むことを特徴とする粘着剤組成物。 - ブロック共重合体の第1ブロックと第2ブロックのガラス転移温度の差が80℃〜150℃の範囲内であることを特徴とする請求項1に記載の粘着剤組成物。
- ブロック共重合体は、第1ブロック100重量部に対して、100重量部〜1,500重量部の第2ブロックを含むことを特徴とする請求項1に記載の粘着剤組成物。
- 第1ブロックは、数平均分子量が3,000〜200,000の範囲内であることを特徴とする請求項1に記載の粘着剤組成物。
- 第2ブロックは、アルキルアクリレートの重合単位を含むことを特徴とする請求項1に記載の粘着剤組成物。
- ブロック共重合体は、数平均分子量が50,000〜300,000の範囲内であることを特徴とする請求項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(Mw/Mn)が1.0〜3.0であることを特徴とする請求項1に記載の粘着剤組成物。
- 多官能性架橋剤をさらに含むことを特徴とする請求項1に記載の粘着剤組成物。
- 酸化防止剤は、フェノール系酸化防止剤、ホスファイト系酸化防止剤及びチオエーテル系酸化防止剤からなる群より選択された一つ以上であることを特徴とする請求項1に記載の粘着剤組成物。
- 光安定剤は、下記化学式Aで表示されることを特徴とする請求項1に記載の粘着剤組成物。
- 酸化防止剤または光安定剤は、ブロック共重合体100重量部に対して0.01〜3重量部で含まれることを特徴とする請求項1に記載の粘着剤組成物。
- 60℃で30日間維持された後の粘度変化率が30%以下であることを特徴とする請求項1に記載の粘着剤組成物。
- 光学フィルム;及び
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に記載の粘着剤組成物を含む粘着剤層を有することを特徴とする粘着型光学積層体。 - 偏光子;及び
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に記載の粘着剤組成物を含む粘着剤層を有することを特徴とする粘着型光学積層体。 - 請求項13に記載の光学積層体または請求項14に記載の偏光板を含むことを特徴とするディスプレイ装置。
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