JP6236468B2 - 粘着剤組成物 - Google Patents
粘着剤組成物 Download PDFInfo
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- JP6236468B2 JP6236468B2 JP2015551597A JP2015551597A JP6236468B2 JP 6236468 B2 JP6236468 B2 JP 6236468B2 JP 2015551597 A JP2015551597 A JP 2015551597A JP 2015551597 A JP2015551597 A JP 2015551597A JP 6236468 B2 JP6236468 B2 JP 6236468B2
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- 239000000178 monomer Substances 0.000 claims description 21
- -1 4-methyl-1-octylpyridinium hexafluorophosphate Chemical compound 0.000 claims description 20
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- 239000003431 cross linking reagent Substances 0.000 claims description 9
- 239000012948 isocyanate Substances 0.000 claims description 8
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- 125000000217 alkyl group Chemical group 0.000 claims description 7
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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 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical class O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
- C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/625—Polymers of alpha-beta ethylenically unsaturated carboxylic acids; hydrolyzed polymers of esters of these acids
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- C—CHEMISTRY; METALLURGY
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
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- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
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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
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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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Description
製造例1−10及び比較製造例1−5
窒素ガスが還流されて温度調節が容易となるように冷却装置を設置した1Lの反応基に下記表1の組成からなる単量体混合物を投入した後、溶剤としてエチルアセテート100重量部を投入した。次に、酸素を除去するために窒素ガスを1時間パージングした後、78℃に維持した。前記混合物を均一にした後、反応開始剤としてアゾビスイソブチロニトリル(AIBN)0.03重量部を投入して、8時間反応させて重量平均分子量が約73万であるアクリル系共重合体を製造した。
下記表2のように、アクリル系共重合体、イオン性帯電防止剤、架橋剤及びシランカップリング剤を混合した後、エチルアセテートで希釈して固形分濃度15%の粘着剤組成物を製造した。
前記実施例及び比較例にて製造された粘着剤組成物、粘着シート、粘着剤付着偏光板の物性を下記の方法で測定して、その結果を下記表3に表した。
製造された粘着剤組成物の初期粘度と常温で24時間放置した後の粘度を粘度測定計(Brookfield LVDV−II+B型(spindle no.3、30rpm))を用いて測定し、粘度の変化率(△η)を計算した。
○:△η<50%
△:50%≦△η<100%
×:100%≦△η
製造された粘着シートを23℃、65%RHで1〜10日間養生しながら1日単位で下記方法によりゲル分率を測定し、ゲル分率がそれ以上増加しない日、すなわち養生期間を測定した。精秤した250メッシュの鉄網(100mm×100mm)に粘着シートの粘着剤層を約0.25g貼付して、ゲルが漏れないように囲む。精密天秤で重量を正確に測定した後、鉄網をエチルアセテート溶液に3日間浸漬する。浸漬された鉄網を取り出して少量のエチルアセテート溶液で洗浄し、120℃で24時間乾燥した後重量を測定する。測定された重量を用いて下記数学式1でゲル分率を計算した。計算されたゲル分率の値が70〜80%範囲に含まれ経時的な変化がない時点を基準に養生期間を決めた。
ゲル分率(%)=(C−A)/(B−A)×100
[式のAは鉄網の重量(g)、Bは粘着剤層を貼付した鉄網の重量(B−A:粘着剤重量、g)、Cは浸漬後乾燥した鉄網の重量(C−A:ゲル化した樹脂の重量、g)である]
製造された粘着剤付着偏光板を90mm×170mmの大きさに切断して離型異形フィルムを剥離させた後、ガラス基板(110mm×190mm×0.7mm)の両面に光学吸収軸が直交するように附着して試験片を製作した。この時、加えられた圧力は5kg/cm2であり、気泡や異物が発生しないようにクリーンルーム作業を行った。耐熱特性は80℃の温度で1000時間放置した後に気泡や剥離の発生可否を観察して、耐湿熱特性は60℃の温度及び90%RHの条件で1000時間放置した後に気泡や剥離の発生可否を観察した。この時、試験片の状態を評価する直前に常温で24時間放置した後観察した。
◎:気泡や剥離なし。
○:気泡や剥離<5個
△:5個≦気泡や剥離<10個
×:10個≦気泡や剥離
粘着剤シートの 離型異形フィルムを剥離した後、表面3地点の表面比抵抗をそれぞれ10回ずつ測定して、その平均値で表した。この時、表面比抵抗は表面抵抗測定器(MCP−HT450/MITSUBISHI CHEMIAL)、Probe(URS、UR100)、Probe Checker(URS用、UR100用)を利用した。
Claims (5)
- 共重合体総含有量100重量部に対して、炭素数1−12のアルキル基を有する(メタ)アクリレート単量体68〜95.9重量部と、(メタ)アクリル酸5〜20重量部及び4−ヒドロキシブチルアクリレート0.5〜2重量部を含むアクリル系共重合体100重量部と、
イソシアネート系架橋剤0.1〜3重量部;及びイオン性帯電防止剤0.1〜5重量部とを含み、
23℃、65%RHで経時変化のない時点である養生期間が24時間以下であり、常温で24時間放置した前後の粘度変化率が50%未満のものであることを特徴とする、粘着剤組成物。 - 前記イオン性帯電防止剤は、ピリジニウム、イミダゾリウム及びテトラアルキルアンモニウムからなる群から選択された陽イオン塩と、
PF6、BF4及びIからなる群から選択された陰イオンであり、イオン性塩類であるものである、請求項1に記載の粘着剤組成物。 - 前記イオン性帯電防止剤は、常温(25℃)で固相のイオン性固体である、請求項2に記載の粘着剤組成物。
- 前記常温(25℃)で固相のイオン性固体は、4−メチル−1−オクチルピリジニウムヘキサフルオロホスフェートまたはトリ−n−ブチルメチルアンモニウムビス−(トリフルオロメタンスルホニル)イミドである、請求項3に記載の粘着剤組成物。
- 前記粘着剤組成物は、シランカップリング剤をさらに含む、請求項2に記載の粘着剤組成物。
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