JP5718308B2 - Antistatic adhesive composition, protective adhesive film, polarizing film and retardation film - Google Patents
Antistatic adhesive composition, protective adhesive film, polarizing film and retardation film Download PDFInfo
- Publication number
- JP5718308B2 JP5718308B2 JP2012273924A JP2012273924A JP5718308B2 JP 5718308 B2 JP5718308 B2 JP 5718308B2 JP 2012273924 A JP2012273924 A JP 2012273924A JP 2012273924 A JP2012273924 A JP 2012273924A JP 5718308 B2 JP5718308 B2 JP 5718308B2
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- JP
- Japan
- Prior art keywords
- group
- sensitive adhesive
- film
- antistatic
- adhesive composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000203 mixture Substances 0.000 title claims description 71
- 239000000853 adhesive Substances 0.000 title claims description 20
- 230000001070 adhesive effect Effects 0.000 title claims description 20
- 230000001681 protective effect Effects 0.000 title claims description 19
- 239000002313 adhesive film Substances 0.000 title claims description 14
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 66
- 239000004014 plasticizer Substances 0.000 claims description 50
- 150000002148 esters Chemical class 0.000 claims description 42
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 41
- 229920000570 polyether Polymers 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 38
- 150000001450 anions Chemical class 0.000 claims description 33
- -1 alkali metal salt Chemical class 0.000 claims description 29
- 125000001153 fluoro group Chemical group F* 0.000 claims description 27
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 27
- 239000004840 adhesive resin Substances 0.000 claims description 15
- 229920006223 adhesive resin Polymers 0.000 claims description 15
- 239000010410 layer Substances 0.000 claims description 15
- 239000012790 adhesive layer Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 25
- 229920005989 resin Polymers 0.000 description 20
- 239000011347 resin Substances 0.000 description 20
- 229920006243 acrylic copolymer Polymers 0.000 description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- 239000000178 monomer Substances 0.000 description 15
- 239000002216 antistatic agent Substances 0.000 description 12
- 150000002430 hydrocarbons Chemical group 0.000 description 12
- 239000003431 cross linking reagent Substances 0.000 description 11
- 230000000740 bleeding effect Effects 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 125000002015 acyclic group Chemical group 0.000 description 8
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- 125000004432 carbon atom Chemical group C* 0.000 description 6
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- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 5
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- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 4
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- 150000002513 isocyanates Chemical class 0.000 description 4
- 229910001416 lithium ion Inorganic materials 0.000 description 4
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- 238000012545 processing Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229920002284 Cellulose triacetate Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 3
- 239000003522 acrylic cement Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N pentadecanoic acid Chemical compound CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 2
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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Landscapes
- Polarising Elements (AREA)
- Adhesive Tapes (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
本発明は、一般に帯電防止性に優れた制電性粘着剤組成物に関するものであり、より特定的にはブリ-ディングやブル-ミングを起こさないように改良された制電性粘着剤組成物に関する。この発明はさらに、そのような制電性粘着剤組成物を用いて得られた保護粘着フィルム、偏光フィルム及び位相差フィルムに関する。 The present invention relates generally to an antistatic pressure-sensitive adhesive composition having excellent antistatic properties, and more specifically, an antistatic pressure-sensitive adhesive composition improved so as not to cause bleeding or blooming. related to. This invention further protective adhesive film obtained using such an antistatic pressure-sensitive adhesive composition, a polarizing film and phase difference film.
近年、樹脂に制電性を付与することが重要になってきており、これを達成するために、従来より、界面活性剤等の帯電防止剤を樹脂成形品の表面に塗布したり、帯電防止剤を樹脂中に練り込む方法が知られている。しかしながら、前者の方法では、長時間経過すると制電性が著しく低下するため、持続性を有する高制電性樹脂として、実用化には供し難い。一方、後者の方法では、帯電防止剤と樹脂との相溶性が悪く、帯電防止剤が成形品の表面から剥離したり、ブリ-ディングやブル-ミングして、制電効果が低下するという課題があった。 In recent years, it has become important to impart antistatic properties to resins. To achieve this, antistatic agents such as surfactants have been conventionally applied to the surface of resin molded products, or antistatic properties have been achieved. A method of kneading an agent into a resin is known. However, in the former method, the antistatic property is remarkably lowered after a long time, so that it is difficult to put it into practical use as a highly antistatic resin having durability. On the other hand, in the latter method, the compatibility between the antistatic agent and the resin is poor, and the antistatic agent is peeled off from the surface of the molded product, or the antistatic effect is reduced due to bleeding or blooming. was there.
また、界面活性剤などの帯電防止剤は、湿度依存性があり、低湿度下では、制電効果が失活する、あるいは、樹脂を成形した後に、帯電防止効果が発現するまでに最低１〜３日掛かり、遅効性であるという課題があった。 Antistatic agents such as surfactants are dependent on humidity, and at low humidity, the antistatic effect is deactivated, or after molding the resin, the antistatic effect is at least 1 to It took 3 days and there was a problem that it was slow-acting.
また、カ-ボンブラックやカ-ボンファイバ-などを樹脂に練り込む方法が提案されている。この方法によると、帯電防止性にすぐれ、帯電防止性に持続性がある樹脂組成物が得られる。しかし、この方法では、透明な成形品が得られなかったり、成形品の色の選択が制限されるなどの課題があった。 In addition, a method of kneading carbon black or carbon fiber into a resin has been proposed. According to this method, a resin composition having excellent antistatic properties and durability in antistatic properties can be obtained. However, this method has a problem that a transparent molded product cannot be obtained, and selection of the color of the molded product is restricted.
本発明者らは、上記の課題を解決する方法として、アルカリ金属またはアルカリ土類金属であるカチオンによって構成される金属塩類を溶解した溶液を、ポリアミド樹脂、ポリエ-テルエステルアミド樹脂、脂肪族ポリエステル、ポリ乳酸系樹脂、熱可塑性エラストマ-及びゴムに添加してなる制電性組成物を提案した(たとえば、特許文献１参照)。 As a method for solving the above problems, the present inventors have prepared a solution in which a metal salt composed of a cation that is an alkali metal or an alkaline earth metal is dissolved in a polyamide resin, a polyetheresteramide resin, an aliphatic polyester. An antistatic composition formed by adding to a polylactic acid resin, a thermoplastic elastomer and rubber has been proposed (for example, see Patent Document 1).
また、ポリウレタンからなる塩改質静電気散逸型重合体(Salt-modified electrostatic dissipative polymers)の製造方法として、リチウムビス(フルオロアルキルスルホニル)イミドを補助溶剤(co-solvents)に溶解して添加する方法が提案されている(特許文献２参照)。 In addition, as a method for producing salt-modified electrostatic dissipative polymers made of polyurethane, there is a method in which lithium bis (fluoroalkylsulfonyl) imide is dissolved in a co-solvent and added. It has been proposed (see Patent Document 2).
しかしながら、この制電性組成物に添加する金属塩類の種類によっては、制電性能が十分でない場合があった。また、過塩素酸等の金属塩類を用いると、この制電性組成物から成るフィルムやシ-トを用いて金属類を包装する場合、金属表面を腐食、発錆あるいは汚染するという欠点があった。 However, depending on the type of metal salt added to the antistatic composition, the antistatic performance may not be sufficient. In addition, the use of metal salts such as perchloric acid has the disadvantage that the metal surface is corroded, rusted or contaminated when the metal is packaged using a film or sheet made of this antistatic composition. It was.
また、特許文献２に記載の方法では、金属塩類を溶解するための補助溶剤（エチレンカ-ボネ-ト、ジメチルスルホキシド、テトラメチレンスルホン、Ｎ-メチル-２-ピロリドン等）が制電性組成物の成形品の表面にブリ-ディングやブル-ミングしてしまい、製品を汚染する。また、成形品の表面を払拭することなどにより制電性が低下し、帯電防止性の耐久性が十分でない。特に、高温高湿度の雰囲気下では、ブリ-ディングやブル-ミングが促進されるため、制電性の低下が著しいという問題点がある。 In the method described in Patent Document 2, an auxiliary solvent for dissolving metal salts (ethylene carbonate, dimethyl sulfoxide, tetramethylene sulfone, N-methyl-2-pyrrolidone, etc.) is used as the antistatic composition. It will bled and bloom on the surface of the molded product, contaminating the product. Further, the antistatic property is lowered by wiping the surface of the molded product, and the durability of the antistatic property is not sufficient. In particular, in an atmosphere of high temperature and high humidity, since bleeding and blooming are promoted, there is a problem that the antistatic property is remarkably lowered.
本発明は、上記問題点に鑑みてなされたものであり、熱安定性に優れ、ブリ-ディング、ブル-ミングおよび移行汚染が発生せず、湿度に依存せずに、速効性に優れ、物性の低下を招かず、かつ、優れた制電性が持続する制電性粘着剤組成物を提供することを目的とする。 The present invention has been made in view of the above problems, has excellent thermal stability, does not cause bleeding, blooming, and migration contamination, does not depend on humidity, has excellent rapidity, and has physical properties. An object of the present invention is to provide an antistatic pressure-sensitive adhesive composition that does not cause a decrease in resistance and maintains excellent antistatic properties.
この発明の他の目的は、そのような制電性粘着剤組成物の製造方法を提供することにある。 Another object of the present invention is to provide a method for producing such an antistatic pressure-sensitive adhesive composition.
この発明のさらに他の目的は、そのような制電性粘着剤組成物を用いた保護粘着フィルムを提供することにある。 Still another object of the present invention is to provide a protective adhesive film using such an antistatic adhesive composition.
この発明のさらに他の目的は、そのような制電性粘着剤組成物を用いた偏光フィルムを提供することにある。 Still another object of the present invention is to provide a polarizing film using such an antistatic pressure-sensitive adhesive composition.
この発明のさらに他の目的は、そのような制電性粘着剤組成物を用いた位相差フィルムを提供することにある。 Still another object of the present invention is to provide a retardation film using such an antistatic pressure-sensitive adhesive composition.
本発明は、粘着性樹脂を含む組成物中に、フルオロ基およびスルホニル基を有する陰イオンを備えた塩が分散されてなる制電性粘着剤組成物に係り、上記フルオロ基およびスルホニル基を有する陰イオンを備えた塩は、下記式（１）に示すポリエーテル基を主鎖中に含むポリエーテルエステル系可塑剤に溶解された状態で分散されていることを特徴とする。
本明細書で、ポリエーテルエステル系可塑剤とは、ポリエーテル基とエステル結合を含む、樹脂の間隙に入り込むことで樹脂が規則正しく配向するのを阻害しガラス遷移点以下でもアモルファス状態を維持するものをいう。上記ポリエーテルエステル系可塑剤には、下記式（２）に示す可塑剤を混合してもよい。
このポリエーテルエステル系可塑剤は、低粘度で作業性が良好であり、低温柔軟性を有し、耐熱老化性、柔軟性と耐久性のバランスがあり、非揮発性、非移行性、耐油性、安全性（ＰＬ適合）に優れる。 This polyether ester plasticizer has low viscosity, good workability, low temperature flexibility, heat aging resistance, balance between flexibility and durability, non-volatility, non-migration, oil resistance Excellent safety (PL conformance).
Ｒは炭素数１〜１４のアルキル基であるのが好ましい。例えば、メチル基、エチル基、ｎ−プロピル基、イソプロピル基、ｎ−ブチル基、イソブチル基、ｎ−ペンチル基、ｎ−ヘキシル基、ｎ−オクチル基、イソオクチル基、２−エチルヘキシル基、ｎ−ノニル基、イソノニル基、ｎ−デシル基、ｎ−ラウリル基などが好ましい。 R is preferably an alkyl group having 1 to 14 carbon atoms. For example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, n-pentyl group, n-hexyl group, n-octyl group, isooctyl group, 2-ethylhexyl group, n-nonyl Group, isononyl group, n-decyl group, n-lauryl group and the like are preferable.
上記 ｍ は、２以上の整数であるのが好ましい。 M is preferably an integer of 2 or more.
ポリエーテル基を主鎖中に含むポリエーテルエステル系可塑剤は、分子量が２５０〜２０００のものが好ましく、より好ましくは５００〜１５００である。粘度（２５℃）は、３０〜６００ｍＰａ・ｓのものが好ましい。 The polyether ester plasticizer containing a polyether group in the main chain preferably has a molecular weight of 250 to 2000, and more preferably 500 to 1500. The viscosity (25 ° C.) is preferably 30 to 600 mPa · s.
この発明によれば、上記フルオロ基及びスルホニル基を有する陰イオンを備えた塩は、上記ポリエーテル基を主鎖中に含むポリエーテルエステル系可塑剤に溶解しやすく、濃度を濃くすることができ、この溶液を分散させることにより、フルオロ基及びスルホニル基を有する陰イオンを備えた塩を、多量にかつ均一に、上記粘着性樹脂中に取り込ませることができる。上記フルオロ基及びスルホニル基を有する陰イオンを備えた塩を溶解したポリエーテルエステル系可塑剤の溶液は、制電性粘着剤組成物中で、上記ポリエーテルエステル系可塑剤の可塑性と相俟って、制電性を発現させながら、可塑性を付与するのである。また、ポリエーテル基を主鎖中に含むポリエーテルエステル系可塑剤は、粘着性樹脂の溶解度パラメータ（ＳＰ値）と近づけることができるので、親和性に優れ、ブリードしない。ひいては、移行汚染が発生せず、湿度に依存せずに、速効性に優れ、かつ優れた制電性が持続する制電性粘着剤組成物を得ることができる。 According to this invention, the salt having an anion having a fluoro group and a sulfonyl group can be easily dissolved in the polyether ester plasticizer containing the polyether group in the main chain, and the concentration can be increased. By dispersing this solution, a salt having an anion having a fluoro group and a sulfonyl group can be incorporated into the adhesive resin in a large amount and uniformly. A solution of a polyether ester plasticizer in which a salt having an anion having a fluoro group and a sulfonyl group is dissolved is compatible with the plasticity of the polyether ester plasticizer in the antistatic pressure-sensitive adhesive composition. Thus, plasticity is imparted while exhibiting antistatic properties. Moreover, since the polyether ester plasticizer containing a polyether group in the main chain can be brought close to the solubility parameter (SP value) of the adhesive resin, it has excellent affinity and does not bleed. As a result, an antistatic pressure-sensitive adhesive composition that does not cause migration contamination, does not depend on humidity, has excellent rapidity, and maintains excellent antistatic properties can be obtained.
本明細書で、「分散」とは、上記塩を溶解したポリエーテルエステル系可塑剤の溶液が、粘着性樹脂を含む組成物中に微液滴状になって散在あるいは溶込んでいる状態をいう。 In this specification, “dispersion” means a state in which a solution of a polyether ester plasticizer in which the salt is dissolved is dispersed or dissolved in the form of fine droplets in a composition containing an adhesive resin. Say.
[粘着性樹脂]
粘着性樹脂は、アクリル系共重合体を含むアクリル系粘着剤が好ましい。
[Adhesive resin]
The adhesive resin is preferably an acrylic adhesive containing an acrylic copolymer.
[アクリル系共重合体]
アクリル系共重合体は、溶液重合法、塊状重合法、懸濁重合法、紫外線照射法、電子線照射法によって共重合させることができる。
[Acrylic copolymer]
The acrylic copolymer can be copolymerized by a solution polymerization method, a bulk polymerization method, a suspension polymerization method, an ultraviolet irradiation method, or an electron beam irradiation method.
中でも、単量体成分として炭素数１〜１４のアルキル基を有する（メタ）アクリル酸エステルを含有するアクリル系共重合体が好ましい。例えば、メチル（メタ）アクリレート、エチル（メタ）アクリレート、ｎ−プロピル（メタ）アクリレート、イソプロピル（メタ）アクリレート、ｎ−ブチル（メタ）アクリレート、イソブチル（メタ）アクリレート、ｎ−ペンチル（メタ）アクリレート、ｎ−ヘキシル（メタ）アクリレート、ｎ−オクチル（メタ）アクリレート、イソオクチル（メタ）アクリレート、２−エチルヘキシル（メタ）アクリレート、ｎ−ノニル（メタ）アクリレート、イソノニル（メタ）アクリレート、ｎ−デシル（メタ）アクリレート、ｎ−ラウリル（メタ）アクリレート等であり、単独或いは２種以上を併用して用いることができる。中でも、ｎ−ブチルアクリレート、２−エチルヘキシルアクリレート、又はそれらを併用した単量体を主成分とすることが好ましく、その使用量は、粘着剤組成中の５０質量％以上であることがより好ましく、９０質量％以上であることが特に好ましい。当該範囲で使用することで、可塑剤がブリードアウトし難く、また、制電性粘着剤組成物を作成した際に架橋が適度に行われるため、剥離力の急激な上昇を抑えやすくなり、より好適に糊残りを低減できる。 Among these, an acrylic copolymer containing a (meth) acrylic acid ester having an alkyl group having 1 to 14 carbon atoms as a monomer component is preferable. For example, methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-nonyl (meth) acrylate, isononyl (meth) acrylate, n-decyl (meth) Examples thereof include acrylate and n-lauryl (meth) acrylate, and can be used alone or in combination of two or more. Among them, n-butyl acrylate, 2-ethylhexyl acrylate, or a monomer using them in combination is preferably a main component, and the amount used is more preferably 50% by mass or more in the pressure-sensitive adhesive composition. It is particularly preferably 90% by mass or more. By using in this range, it is difficult for the plasticizer to bleed out, and when the antistatic pressure-sensitive adhesive composition is prepared, crosslinking is moderately performed. The adhesive residue can be suitably reduced.
上記アクリル系共重合体は官能基を付与する単量体として、側鎖に水酸基、カルボキシル基、アミノ基などの極性基を有する（メタ）アクリル酸エステル単量体やその他のビニル系単量体を含有することが好ましい。極性基を有する単量体の含有量は、アクリル系共重合体を構成する単量体成分の０．１〜１５質量％であることが好ましく、１〜１０質量％であることがより好ましい。当該範囲で含有することにより、粘着剤の凝集力、接着性を好適な範囲に調整しやすい。 The acrylic copolymer is a monomer that gives a functional group, and a (meth) acrylic acid ester monomer or other vinyl monomer having a polar group such as a hydroxyl group, a carboxyl group, or an amino group in the side chain. It is preferable to contain. The content of the monomer having a polar group is preferably from 0.1 to 15% by mass, more preferably from 1 to 10% by mass, based on the monomer component constituting the acrylic copolymer. By containing in the said range, it is easy to adjust the cohesive force and adhesiveness of an adhesive to a suitable range.
水酸基を有する単量体としては、例えば２−ヒドロキシエチル（メタ）アクリレート、４−ヒドロキシブチル（メタ）アクリレート、６−ヒドロキシヘキシル（メタ）アクリレート、ヒドロキシプロピル（メタ）アクリレート、カプロラクトン変性（メタ）アクリレート、ポリエチレングリコールモノ（メタ）アクリレート、ポリプロピレングリコール（メタ）アクリレート等の水酸基含有（メタ）アクリレートを使用でき、中で２−ヒドロキシエチル（メタ）アクリレート、４−ヒドロキシブチル（メタ）アクリレート、６−ヒドロキシヘキシル（メタ）アクリレートを共重合成分として使用するのが好ましい。 Examples of the monomer having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, hydroxypropyl (meth) acrylate, and caprolactone-modified (meth) acrylate. Hydroxyl group-containing (meth) acrylates such as polyethylene glycol mono (meth) acrylate and polypropylene glycol (meth) acrylate can be used, among which 2-hydroxyethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxy It is preferred to use hexyl (meth) acrylate as a copolymerization component.
カルボキシル基を有する単量体としては、アクリル酸、メタクリル酸、イタコン酸、マレイン酸、クロトン酸、（メタ）アクリル酸２量体、エチレンオキサイド変性コハク酸アクリレート等を使用でき、なかでもアクリル酸を共重合成分として使用するのが好ましい。 As the monomer having a carboxyl group, acrylic acid, methacrylic acid, itaconic acid, maleic acid, crotonic acid, (meth) acrylic acid dimer, ethylene oxide-modified succinic acid acrylate, etc. can be used. It is preferable to use it as a copolymerization component.
窒素原子を有する単量体としては、Ｎ−ビニル−２−ピロリドン、Ｎ−ビニルカプロラクタム、アクリロイルモルホリン、アクリルアミド、Ｎ，Ｎ−ジメチルアクリルアミド、２−（パーヒドロフタルイミド−Ｎ−イル）エチルアクリレート等のアミド基含有ビニルモノマーを使用でき、中でもＮ−ビニル−２−ピロリドン、Ｎ−ビニルカプロラクタム、アクリロイルモルホリンを共重合成分として使用するのが好ましい。 Examples of the monomer having a nitrogen atom include N-vinyl-2-pyrrolidone, N-vinylcaprolactam, acryloylmorpholine, acrylamide, N, N-dimethylacrylamide, and 2- (perhydrophthalimido-N-yl) ethyl acrylate. An amide group-containing vinyl monomer can be used, and among these, N-vinyl-2-pyrrolidone, N-vinylcaprolactam, and acryloylmorpholine are preferably used as the copolymerization component.
その他の極性基を有するビニル系単量体として、酢酸ビニル、アクリロニトリル、無水マレイン酸、無水イタコン酸などが挙げられる。 Examples of vinyl monomers having other polar groups include vinyl acetate, acrylonitrile, maleic anhydride, itaconic anhydride and the like.
また、上記アクリル系共重合体の重量平均分子量は、３０万〜１４０万の範囲内であることが好ましい。重量平均分子量はゲルパーミエーションクロマトグラフィー（ＧＰＣ）を用いて測定することができ、標準ポリスチレン（ＰＳ）に換算した重量平均分子量を示す。重量平均分子量が３０万以上であると、低分子量物による被着体表面の汚染が生じ難くなる傾向がある。更に、重量平均分子量を１４０万以下に抑制すると、粘着剤溶液の粘度の上昇による塗工作業時のスジ等の問題が発生しないという利点がある。 The acrylic copolymer preferably has a weight average molecular weight in the range of 300,000 to 1,400,000. A weight average molecular weight can be measured using a gel permeation chromatography (GPC), and shows the weight average molecular weight converted into standard polystyrene (PS). When the weight average molecular weight is 300,000 or more, contamination of the adherend surface with a low molecular weight product tends to be difficult to occur. Furthermore, when the weight average molecular weight is suppressed to 1.4 million or less, there is an advantage that problems such as streaks during coating work due to an increase in the viscosity of the pressure-sensitive adhesive solution do not occur.
[可塑剤]
粘着性樹脂には上記ポリエーテルエステル系可塑剤とは別に、さらなる可塑剤を追加してもよい。そのような可塑剤として、飽和又は不飽和の非環式炭化水素基を有するモノ又はジカルボン酸と、炭素数１〜２０の非環式炭化水素基を有するアルコールとから形成されるエステル、あるいは、前記不飽和の非環式炭化水素基中の不飽和基がエポキシ化されたエステルからなる可塑剤を使用する。本発明においては、可塑剤として当該環状骨格を有さないエステルを使用することで、粘着剤層の被着体に対する濡れ性を向上させることができ、貼り付け時に気泡の巻き込みを生じ難くできると共に、粘着剤層からの可塑剤のブリードアウトが生じ難くなり被着体汚染を好適に低減できる。
[Plasticizer]
In addition to the polyether ester plasticizer, an additional plasticizer may be added to the adhesive resin. As such a plasticizer, an ester formed from a mono- or dicarboxylic acid having a saturated or unsaturated acyclic hydrocarbon group and an alcohol having an acyclic hydrocarbon group having 1 to 20 carbon atoms, or A plasticizer comprising an ester in which the unsaturated group in the unsaturated acyclic hydrocarbon group is epoxidized is used. In the present invention, by using an ester having no cyclic skeleton as a plasticizer, the wettability of the pressure-sensitive adhesive layer to the adherend can be improved, and it is difficult to cause entrainment of bubbles at the time of attachment. Further, bleeding out of the plasticizer from the pressure-sensitive adhesive layer hardly occurs, and adherend contamination can be suitably reduced.
エステルを構成するモノ又はジカルボン酸成分における飽和又は不飽和の非環式炭化水素基としては、アルキル基やアルキレン基を使用でき、なかでも炭素数が１〜２０のアルキル基又はアルキレン基が好ましく、炭素数４〜１８のアルキル基であることがさらに好ましく、炭素数４〜１４のアルキル基が特に好ましい。このような飽和又は不飽和の非環式炭化水素基を有するモノ又はジカルボン酸は、粘着剤層に使用されるアクリル共重合体を構成するアクリル単量体の炭素数と近い炭素数を有することにより、制電性粘着剤組成物との相溶性が良好になり、可塑剤アクリル系制電性粘着剤組成物中に好適に保持されるため、ブリードアウトが抑制される。 As the saturated or unsaturated acyclic hydrocarbon group in the mono- or dicarboxylic acid component constituting the ester, an alkyl group or an alkylene group can be used, among which an alkyl group or alkylene group having 1 to 20 carbon atoms is preferable. It is more preferable that it is a C4-C18 alkyl group, and a C4-C14 alkyl group is especially preferable. The mono- or dicarboxylic acid having such a saturated or unsaturated acyclic hydrocarbon group has a carbon number close to that of the acrylic monomer constituting the acrylic copolymer used in the pressure-sensitive adhesive layer. Thus, compatibility with the antistatic pressure-sensitive adhesive composition is improved, and the plasticizer acrylic antistatic pressure-sensitive adhesive composition is suitably retained, so that bleeding out is suppressed.
これら飽和又は不飽和の非環式炭化水素基を有するモノカルボン酸及びジカルボン酸としては、例えば、シュウ酸、マロン酸、コハク酸、グルタル酸、アジピン酸、ピメリン酸、スベリン酸、アゼライン酸、セバシン酸、ドデカン二酸等の直鎖脂肪族ジカルボン酸のモノ又はポリエステル、酢酸、プロピオン酸、酪酸、キツソウ酸、カプロン酸、エナント酸、カプリル酸、ペラルゴン酸、カプリン酸、ウンデシル酸、ラウリン酸、トリデシル酸、ミリスチン酸、ペンタデシル酸、パルチミン酸、マルガリン酸、ステアリン酸、ノナデシル酸、アラキン酸等の飽和脂肪酸、クロトン酸、アンゲリカ酸、リンデル酸、ミリストレイン酸、パルミトレイン酸、オレイン酸、バクセン酸、ガドレイン酸、エイコセン酸、エルカ酸、ネルボン酸、リノール酸、エイコサジエン酸、ドコサジエン酸、リノレン酸、ピノレン酸、エレオステアリン酸、ミード酸、ステアリドン酸、アラキドン酸、エイコサテトラエン酸、アドレン酸、エライジン酸、ドコサヘキサエン酸等の不飽和脂肪酸などが挙げられる。 Examples of the monocarboxylic acid and dicarboxylic acid having a saturated or unsaturated acyclic hydrocarbon group include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, and sebacin. Mono- or polyester of linear aliphatic dicarboxylic acid such as acid, dodecanedioic acid, acetic acid, propionic acid, butyric acid, chitosulic acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, undecyl acid, lauric acid, tridecyl Acids, myristic acid, pentadecylic acid, palmitic acid, margaric acid, stearic acid, nonadecylic acid, arachidic acid, etc. Acid, eicosenoic acid, erucic acid, nervonic acid, linault Examples include unsaturated fatty acids such as acid, eicosadienoic acid, docosadienoic acid, linolenic acid, pinolenic acid, eleostearic acid, mead acid, stearidonic acid, arachidonic acid, eicosatetraenoic acid, adrenic acid, elaidic acid, docosahexaenoic acid, etc. It is done.
エステルを構成するアルコールにおける炭素数１〜２０の非環式炭化水素基としては、炭素数が１〜２０のアルキル基やアルキレン基、特にアルキル基を好適に使用でき、なかでも、炭素数４〜１８のアルキル基が好ましく、炭素数４〜１４のアルキル基が特に好ましい。このような飽和又は不飽和の非環式炭化水素基を有するアルコールは、粘着剤層に使用されるアクリル共重合体を構成するアクリル単量体の炭素数と近い炭素数を有することにより、制電性粘着剤組成物との相溶性が良好になり、可塑剤アクリル系制電性粘着剤組成物中に好適に保持されるため、ブリードアウトが抑制される。本発明においては、エステルを構成するカルボン酸成分に比して、当該アルコール成分の有する炭化水素基の炭素数を、粘着剤層に使用されるアクリル共重合体を構成するアクリル単量体の炭素数と近い炭素数とすることで、特に被着体汚染を抑制しやすくなる。 As a C1-C20 acyclic hydrocarbon group in the alcohol which comprises ester, a C1-C20 alkyl group and an alkylene group, especially an alkyl group can be used conveniently, Especially, C4-C4 An 18 alkyl group is preferable, and an alkyl group having 4 to 14 carbon atoms is particularly preferable. Such an alcohol having a saturated or unsaturated acyclic hydrocarbon group has a carbon number close to that of the acrylic monomer constituting the acrylic copolymer used in the pressure-sensitive adhesive layer. Since the compatibility with the electric pressure-sensitive adhesive composition is improved and it is suitably held in the plasticizer acrylic antistatic pressure-sensitive adhesive composition, bleeding out is suppressed. In the present invention, as compared with the carboxylic acid component constituting the ester, the number of carbon atoms of the hydrocarbon group of the alcohol component is the carbon of the acrylic monomer constituting the acrylic copolymer used in the pressure-sensitive adhesive layer. By setting the number of carbons to be close to the number, it is particularly easy to suppress adherend contamination.
このような非環式炭化水素基を有するアルコールとしては、例えば、メチルアルコール、エチルアルコール、プロパノール、ブタノール、ペンタノール、ヘキサノール、ヘプタノール、オクチルアルコール、ノニルアルコール、デシルアルコール、ウンデシルアルコール、ドデシルアルコール、トリデシルアルコール、テトラデシルアルコール、ペンタデシルアルコール、セチルアルコール、ヘプタデシルアルコール、オクタデシルアルコール、ノナデシルアルコール、アラキルアルコールの直鎖、分岐アルコールが挙げられる。なかでも、ブタノール、ペンタノール、ヘキサノール、ヘプタノール、オクチルアルコール、ノニルアルコール、デシルアルコールが特に好ましく使用できる。 Examples of the alcohol having such an acyclic hydrocarbon group include methyl alcohol, ethyl alcohol, propanol, butanol, pentanol, hexanol, heptanol, octyl alcohol, nonyl alcohol, decyl alcohol, undecyl alcohol, dodecyl alcohol, Examples include tridecyl alcohol, tetradecyl alcohol, pentadecyl alcohol, cetyl alcohol, heptadecyl alcohol, octadecyl alcohol, nonadecyl alcohol, and straight chain or branched alcohol of aralkyl alcohol. Of these, butanol, pentanol, hexanol, heptanol, octyl alcohol, nonyl alcohol, and decyl alcohol can be particularly preferably used.
さらに好ましくは、上記のモノ又はジカルボン酸と、アルコールとから形成されるエステルを可塑剤として使用する。当該エステルとしては、飽和又は不飽和の炭化水素基からなる骨格を有するものであってもよいが、不飽和の炭化水素基からなる骨格を有さないエステルであることが好ましい。また、当該不飽和の炭化水素基からなる骨格を有するエステルの不飽和結合がエポキシ化されたエポキシ化エステルも好ましく使用できる。当該エステルのなかでも、アジピン酸モノエステル、セバシン酸モノエステル、エポキシ化脂肪酸モノエステルを特に好ましく使用できる。 More preferably, an ester formed from the above mono- or dicarboxylic acid and an alcohol is used as a plasticizer. The ester may have a skeleton composed of a saturated or unsaturated hydrocarbon group, but is preferably an ester not having a skeleton composed of an unsaturated hydrocarbon group. Moreover, an epoxidized ester in which an unsaturated bond of an ester having a skeleton composed of the unsaturated hydrocarbon group is epoxidized can also be preferably used. Among the esters, adipic acid monoester, sebacic acid monoester, and epoxidized fatty acid monoester can be particularly preferably used.
可塑剤として使用するエステルとしては、モノエステル又はポリエステルのいずれであってもよいが、ＳＰ値を好適な範囲に制御しやすく、粘着剤との相溶性を向上させやすいことから、ＰＳ換算での重量平均分子量が、１０００以下のエステルであることが好ましく、３００〜８００のエステルであることが特に好ましい。 The ester used as the plasticizer may be either a monoester or a polyester, but it is easy to control the SP value within a suitable range and easily improve the compatibility with the pressure-sensitive adhesive. The ester having a weight average molecular weight of 1000 or less is preferable, and an ester having a weight average molecular weight of 300 to 800 is particularly preferable.
上記可塑剤として溶解度パラメーター（ＳＰ値）が８．５以下の可塑剤を使用するのが好ましい。中でも、７．０〜８．４であることが好ましい。可塑剤のＳＰ値が８．５以下であるとアクリル系粘着剤共重合体との相溶性に優れるため被着対象表面に粘着フィルムを貼付した状態で高温高湿環境下にて長時間放置した際、被着対象表面から剥離した際に被着対象表面に曇りが発生し難い。可塑剤のＳＰ値としては７．０よりも大きい可塑剤が汎用で使用される。なお、上記ＳＰ値は J. Smallが提唱している Small式［P.A.J.Small:J.Appl.Chem.,3,71(1953)］による計算値である。 It is preferable to use a plasticizer having a solubility parameter (SP value) of 8.5 or less as the plasticizer. Especially, it is preferable that it is 7.0-8.4. If the SP value of the plasticizer is 8.5 or less, it is excellent in compatibility with the acrylic pressure-sensitive adhesive copolymer. Therefore, the plasticizer is left for a long time in a high-temperature and high-humidity environment with a pressure-sensitive adhesive film applied to the surface to be adhered. In this case, the surface of the deposition target is less likely to be clouded when peeled off from the surface of the deposition target. As the SP value of the plasticizer, a plasticizer having a value larger than 7.0 is generally used. The SP value is a value calculated by the small formula [P.A.J.Small: J.Appl.Chem., 3, 71 (1953)] proposed by J. Small.
上記可塑剤は、上記アクリル系粘着剤を構成する（メタ）アクリル共重合体１００重量部に対して、０．５重量部以上３０重量部以下添加することが好ましく、１重量部以上２０重量部以下添加することがより好ましく、１重量部以上１０重量部以下添加することが特に好ましい。可塑剤の添加量が０．５重量部より多いと手貼りした際に気泡が抜け易くなる。また、３０重量部より少ないと、高温高湿環境下においてもディスプレイ表面に曇りが発生し難いという特長を有する。 The plasticizer is preferably added in an amount of 0.5 to 30 parts by weight with respect to 100 parts by weight of the (meth) acrylic copolymer constituting the acrylic pressure-sensitive adhesive. It is more preferable to add below, and it is especially preferable to add 1 to 10 parts by weight. When the added amount of the plasticizer is more than 0.5 parts by weight, the bubbles are easily removed when manually pasted. Further, when the amount is less than 30 parts by weight, the display surface is less likely to fog up even in a high temperature and high humidity environment.
[架橋剤] [Crosslinking agent]
粘着剤層の凝集力をあげるために、前記アクリル系制電性粘着剤組成物に架橋剤を添加するのが好ましい。架橋剤としては、例えば、イソシアネート系架橋剤、エポキシ系架橋剤、キレート系架橋剤、アジリジン系架橋剤等が挙げられる。中でもイソシアネート架橋剤を使用すると、得られるフィルムのエア抜け性を向上させやすいため好ましく使用できる。 In order to increase the cohesive strength of the pressure-sensitive adhesive layer, it is preferable to add a crosslinking agent to the acrylic antistatic pressure-sensitive adhesive composition. Examples of the crosslinking agent include an isocyanate crosslinking agent, an epoxy crosslinking agent, a chelate crosslinking agent, and an aziridine crosslinking agent. Among these, when an isocyanate crosslinking agent is used, it is preferable to use it because it is easy to improve the air bleeding property of the obtained film.
架橋剤の添加量としては、粘着剤層のゲル分率を８０〜９９％になるよう調整するのが好ましい。さらに好ましいゲル分率は、９０〜９９％である。当該ゲル分率の範囲とすることで、低分子量成分の割合が少なくなり、粘着剤層の容易な脱落を防ぎやすくなり特に好適に糊残りを低減できる。なお、ゲル分率は、養生後の粘着剤層組成物をトルエン中に浸漬し、２４時間放置後に残った不溶分の乾燥後の質量を測定し、元の質量に対する百分率で表す。 The addition amount of the crosslinking agent is preferably adjusted so that the gel fraction of the pressure-sensitive adhesive layer is 80 to 99%. A more preferable gel fraction is 90 to 99%. By setting it as the range of the said gel fraction, the ratio of a low molecular weight component decreases, it becomes easy to prevent easy drop-off of an adhesive layer, and it can reduce especially adhesive residue suitably. In addition, a gel fraction immerses the adhesive layer composition after curing in toluene, measures the mass after drying of the insoluble part which remained after leaving for 24 hours, and represents it as a percentage with respect to the original mass.
[フルオロ基およびスルホニル基を有する陰イオンを備えた塩]
上記フルオロ基及びスルホニル基を有する陰イオンを備えた塩は、アルカリ金属、２Ａ族元素、遷移金属、両性金属のいずれかの陽イオンと、上記フルオロ基及びスルホニル基を有する陰イオンとからなる塩であるのが好ましい。
[Salt with anion having a fluoro group and a sulfonyl group]
The salt having an anion having a fluoro group and a sulfonyl group is a salt comprising an anion having an alkali metal, a group 2A element, a transition metal or an amphoteric metal, and the anion having the fluoro group and the sulfonyl group. Is preferred.
上記フルオロ基及びスルホニル基を有する陰イオンを備えた塩は、特にビス（トリフルオロメタンスルホニル）イミドのアルカリ金属塩又はトリフルオロメタンスルホン酸イオンのアルカリ金属塩であるのが好ましい。リチウム塩が特に好ましい。 The salt having an anion having a fluoro group and a sulfonyl group is particularly preferably an alkali metal salt of bis (trifluoromethanesulfonyl) imide or an alkali metal salt of trifluoromethanesulfonate ion. Lithium salts are particularly preferred.
上記フルオロ基およびスルホニル基を有する陰イオンを備えた塩は、上記ポリエーテルエステル系可塑剤１００質量部に対して、０．１質量部以上２００質量部以下の割合で、上記ポリエーテルエステル系可塑剤に溶解されているのが好ましい。 The salt having an anion having a fluoro group and a sulfonyl group is in a proportion of 0.1 to 200 parts by mass with respect to 100 parts by mass of the polyether ester plasticizer. It is preferably dissolved in the agent.
上記粘着性樹脂１００質量部に対して、上記フルオロ基およびスルホニル基を有する陰イオンを備えた塩は、０．０１質量部以上３０質量部以下含まれるのが好ましい。 It is preferable that the salt provided with the anion which has the said fluoro group and a sulfonyl group with respect to 100 mass parts of said adhesive resins is contained 0.01 mass part or more and 30 mass parts or less.
このように規制するのは、上記陰イオンを備えた塩の配合量が、０．０１質量部未満であると、制電性が十分発現されないからである。一方、上記陰イオンを備えた塩の配合量が、３０質量部を超えると、制電性付与効果が飽和するので、コスト高を招来するという問題があるからである。 The reason for this regulation is that the antistatic property is not sufficiently exhibited when the amount of the salt having the anion is less than 0.01 parts by mass. On the other hand, if the amount of the salt having an anion exceeds 30 parts by mass, the antistatic effect is saturated, resulting in a problem of high cost.
[重合体型帯電防止剤]
上記制電性粘着剤組成物は、さらに重合体型帯電防止剤を含んでもよい。本発明の制電性粘着剤組成物に重合体型帯電防止剤を含めると、上記陰イオンを備えた塩を安定化することができることが見出された。また、上記陰イオンを備えた塩はポリエーテル基を主鎖中に含むポリエーテルエステル系可塑剤に溶解された状態で分散されるので、この塩はポリエーテル基を主鎖中に含むポリエーテルエステル系可塑剤と親和性を有する重合体型帯電防止剤の存在する所に、集まり、両者の親和力により安定化したものと考えられる。このような重合体型帯電防止剤としては、ポリエ−テルブロックポリオレフィン共重合体、ポリオキシアルキレン系共重合体又はエチレンオキサイド−プロピレンオキサイド−アリルグリシジル共重合体が挙げられる。
[Polymer type antistatic agent]
The antistatic pressure-sensitive adhesive composition may further contain a polymer-type antistatic agent. It has been found that the inclusion of a polymer-type antistatic agent in the antistatic pressure-sensitive adhesive composition of the present invention can stabilize the salt having the anion. Further, since the salt having an anion is dispersed in a polyether ester plasticizer containing a polyether group in the main chain, the salt is a polyether containing a polyether group in the main chain. It is considered that the polymer type antistatic agent having an affinity for the ester plasticizer gathers and is stabilized by the affinity of both. Examples of such a polymer type antistatic agent include a polyether block polyolefin copolymer, a polyoxyalkylene copolymer, and an ethylene oxide-propylene oxide-allyl glycidyl copolymer.
上記粘着性樹脂１００質量部に対して、上記重合体型帯電防止剤を、０．１質量部以上６５質量部以下の割合で含有していればよい。 What is necessary is just to contain the said polymer type antistatic agent in the ratio of 0.1 to 65 mass parts with respect to 100 mass parts of said adhesive resins.
このように規制するのは、上記重合体型帯電防止剤の配合量が０．１質量部未満であると、制電性が十分発現されないからである。一方、上記重合体型帯電防止剤の配合量が６５質量部を超えると、制電性付与効果が飽和するので、コスト高を招来するという問題があるからである。また、組成物の物性が失われることがあるからである。 The reason for this regulation is that the antistatic property is not sufficiently exhibited when the blending amount of the polymer type antistatic agent is less than 0.1 parts by mass. On the other hand, when the blending amount of the polymer type antistatic agent exceeds 65 parts by mass, the antistatic effect is saturated, resulting in a problem of high cost. Moreover, it is because the physical property of a composition may be lost.
本発明の制電性粘着剤組成物には、さらに酸化防止剤、熱安定剤、紫外線吸収剤、難燃剤、難燃助剤、着色剤、顔料、抗菌・抗カビ剤、耐光剤、可塑剤、粘着付与剤、分散剤、消泡剤、硬化触媒、硬化剤、レベリング剤、撥水剤、カップリング剤、フィラ−、加硫剤、キレート剤、加硫促進剤などの公知の添加剤を必要に応じて添加することができる。 The antistatic pressure-sensitive adhesive composition of the present invention further includes an antioxidant, a heat stabilizer, an ultraviolet absorber, a flame retardant, a flame retardant aid, a colorant, a pigment, an antibacterial / antifungal agent, a light fastener, and a plasticizer. Known additives such as tackifiers, dispersants, antifoaming agents, curing catalysts, curing agents, leveling agents, water repellents, coupling agents, fillers, vulcanizing agents, chelating agents, and vulcanization accelerators. It can be added as necessary.
本発明の他の局面に従う発明は、基材と粘着剤層とを有する保護粘着フィルム、偏光フィルム又は位相差フィルムであって、上記粘着剤層が上述の制電性粘着剤組成物から形成されていることを特徴とする。 The invention according to another aspect of the present invention is a protective adhesive film, a polarizing film or a retardation film having a substrate and an adhesive layer, wherein the adhesive layer is formed from the antistatic adhesive composition described above. It is characterized by.
また、本発明の保護粘着フィルム、偏光フィルム又は位相差フィルムは、各種ディスプレイ、偏光板等の光学部材に利用され、好適な透明性にすぐれ、着色もほとんどなく、再剥離性にすぐれ、剥離時の剥離帯電が少ない。 Further, the protective adhesive film, polarizing film or retardation film of the present invention is used for optical members such as various displays and polarizing plates, and has excellent transparency, little coloration, excellent removability, and upon peeling. There is little peeling charge.
上記基材としては、一般に粘着フィルムに使用される基材であれば特に限定されず、二軸延伸フィルム、一軸延伸フィルム、無延伸フィルムのいずれも使用できる。このようなプラスチックフィルムには、ポリオレフィン系樹脂フィルムが好適に用いられ、例えば、低密度ポリエチレン樹脂、直鎖状低密度ポリエチレン樹脂、高密度ポリエチレン樹脂、ポリプロピレン樹脂、エチレン−プロピレン共重合樹脂等の樹脂フィルムなどが挙げられる。より具体的には、ポリエチレンテレフタレート（ＰＥＴ）、ポリブチレンテレフタレート、ポリエチレンナフタレート、ポリエチレンフィルム、ポリプロピレンフィルム、セロファン、ジアセチルセルロースフィルム、トリアセチルセルロースフィルム、アセチルセルロースブチレートフィルム、ポリ塩化ビニルフィルム、ポリ塩化ビニリデンフィルム、ポリビニルアルコールフィルム、エチレン−酢酸ビニル共重合体フィルム、ポリスチレンフィルム、ポリカーボネートフィルム、ポリメチルペンテンフィルム、ポリスルホンフィルム、ポリエーテルエーテルケトンフィルム、ポリエーテルスルホンフィルム、ポリエーテルイミドフィルム、ポリイミドフィルム、フッソ樹脂フィルム、ナイロンフィルム、アクリル樹脂フィルム等を挙げることができる。このうち、透明性に優れる直鎖状低密度ポリエチレン樹脂、エチレン−プロピレン共重合樹脂等の樹脂フィルムがより好ましく、中でも、ＰＥＴフィルムは、スリップ剤等の添加剤を用いなくともハンドリングが良好であるため、添加剤による被着体表面の汚染可能性を低減させることができ、高い透明性を有するため粘着フィルムを貼付した状態で検査を行う事ができるという利点があるため特に好ましく使用できる。更に、引張強度が強く、腰があるため貼付時に貼付部以外の粘着フィルムの一部が被着体に接触することによって生じる気泡巻き込みが生じ難く、加工時のハンドリング性に優れる二軸延伸のＰＥＴフィルムがより好ましい。 The substrate is not particularly limited as long as it is a substrate generally used for an adhesive film, and any of a biaxially stretched film, a uniaxially stretched film, and an unstretched film can be used. For such a plastic film, a polyolefin-based resin film is preferably used. For example, a resin such as a low-density polyethylene resin, a linear low-density polyethylene resin, a high-density polyethylene resin, a polypropylene resin, or an ethylene-propylene copolymer resin. A film etc. are mentioned. More specifically, polyethylene terephthalate (PET), polybutylene terephthalate, polyethylene naphthalate, polyethylene film, polypropylene film, cellophane, diacetyl cellulose film, triacetyl cellulose film, acetyl cellulose butyrate film, polyvinyl chloride film, polyvinyl chloride Vinylidene film, polyvinyl alcohol film, ethylene-vinyl acetate copolymer film, polystyrene film, polycarbonate film, polymethylpentene film, polysulfone film, polyetheretherketone film, polyethersulfone film, polyetherimide film, polyimide film, fluorine Resin film, nylon film, acrylic resin film, etc. Door can be. Of these, resin films such as linear low-density polyethylene resin and ethylene-propylene copolymer resin, which are excellent in transparency, are more preferable, and among them, PET film has good handling without using additives such as slip agents. Therefore, the possibility of contamination of the adherend surface due to the additive can be reduced, and since it has high transparency, there is an advantage that it can be inspected with the adhesive film attached, so that it can be particularly preferably used. Furthermore, because of its high tensile strength and low waist, it is difficult for air bubbles to be generated when a part of the adhesive film other than the application part comes into contact with the adherend at the time of application, and it is a biaxially stretched PET that excels in handling during processing. A film is more preferable.
上記基材の厚さとしては、特に限定されないが、１０〜１５０μｍが好ましく、２５〜１００μｍが更に好ましく、３８〜１００μｍが特に好ましい。１０μｍより厚いとフィルム強度が十分な保護性能が得られる耐久性を有するため、剥離時にフィルムが破れる等の問題が発生し難く、また２５μｍ以上では手貼りに適した柔軟性を得られる。また、１５０μｍより薄いとエッジ部の引っかかりによる剥がれの問題が生じ難く、１００μｍ以下ではフィルムの光透過性が良好であり、フィルム自体が高価になる等の問題が発生しない。 Although it does not specifically limit as thickness of the said base material, 10-150 micrometers is preferable, 25-100 micrometers is still more preferable, 38-100 micrometers is especially preferable. If it is thicker than 10 μm, the film strength is durable enough to obtain a protective performance, so that problems such as tearing of the film at the time of peeling hardly occur, and if it is 25 μm or more, flexibility suitable for manual attachment can be obtained. On the other hand, if the thickness is less than 150 μm, the problem of peeling due to catching of the edge portion hardly occurs, and if it is 100 μm or less, the light transmittance of the film is good, and the problem that the film itself becomes expensive does not occur.
本発明の基材の弾性率としては１〜７ＧＰａが好ましい。弾性率が１ＧＰａ以上であると、粘着フィルムを形成した際にフィルム基材の変形が生じ難く、７ＧＰａ以下であると、フィルム基材が緩やかな曲面への粘着フィルムの貼り付け時も追従できる程度の硬さを有する。 The elastic modulus of the substrate of the present invention is preferably 1 to 7 GPa. If the elastic modulus is 1 GPa or more, deformation of the film base material hardly occurs when the adhesive film is formed, and if it is 7 GPa or less, the film base material can follow even when the adhesive film is attached to a gently curved surface. Of hardness.
上記記載の基材表面には、ＰＯＰ等の表示機能を持たせる目的で印刷を行う場合には、インキ密着性を向上させるために、アンカーコート層を設けることができる。 When printing is performed for the purpose of providing a display function such as POP on the surface of the substrate described above, an anchor coat layer can be provided in order to improve ink adhesion.
上記記載の基材表面には、表面の傷付き防止を目的として、ハードコート層を設けることができる。 A hard coat layer can be provided on the surface of the substrate described above for the purpose of preventing scratches on the surface.
本発明では、粘着性樹脂を含む組成物中に、フルオロ基およびスルホニル基を有する陰イオンを備えた塩が分散されてなる制電性粘着剤組成物において、上記フルオロ基およびスルホニル基を有する陰イオンを備えた塩は、ポリエーテル基を主鎖中に含むポリエーテルエステル系可塑剤に溶解された状態で分散されている。フルオロ基及びスルホニル基を有する陰イオンを備えた塩は、上記ポリエーテルエステル系可塑剤を介して粘着性樹脂を含む組成物中に、均一に親和する。フルオロ基及びスルホニル基を有する陰イオンを備えた塩は、高い導電率、高い耐熱性、不燃性を有するので、制電性・熱安定性に優れ、金属を腐食せず、湿度などの環境によらない制電性粘着剤組成物を得ることができる。 In the present invention, an antistatic pressure-sensitive adhesive composition in which a salt having an anion having a fluoro group and a sulfonyl group is dispersed in a composition containing an adhesive resin, the anion having the fluoro group and the sulfonyl group is used. The salt with ions is dispersed in a state dissolved in a polyether ester plasticizer containing a polyether group in the main chain. A salt having an anion having a fluoro group and a sulfonyl group has a uniform affinity in the composition containing an adhesive resin via the polyether ester plasticizer. Salts with anions having a fluoro group and a sulfonyl group have high electrical conductivity, high heat resistance, and nonflammability, so they have excellent antistatic and thermal stability, do not corrode metals, and can be used in environments such as humidity. An antistatic adhesive composition that does not depend can be obtained.
熱安定性に優れ、ブリ-ディング、ブル-ミングおよび移行汚染が発生せず、湿度に依存せずに、速効性に優れ、物性の低下を招かず、かつ、優れた制電性が持続する制電性粘着剤組成物を得るという目的を、フルオロ基およびスルホニル基を有する陰イオンを備えた塩を、ポリエーテル基を主鎖中に含むポリエーテルエステル系可塑剤に溶解させて、粘着性樹脂を含む組成物中に分散させることによって実現した。 Excellent thermal stability, no bleeding, blooming and migration contamination, no dependence on humidity, excellent fast-acting properties, no deterioration in physical properties, and excellent antistatic performance For the purpose of obtaining an antistatic pressure-sensitive adhesive composition, a salt having an anion having a fluoro group and a sulfonyl group is dissolved in a polyether ester plasticizer containing a polyether group in the main chain. This was realized by dispersing in a composition containing a resin.
上記塩として、ビス（トリフルオロメタンスルホニル）イミドリチウムを用い、ジエチレングリコールとアジピン酸とからなるポリエーテルエステル系可塑剤に溶解した状態は、図１に示すように、ポリエチレングリコール中のエーテル酸素原子にリチウムイオンが配位した状態になっている。粘着層を形成すると、エーテル酸素原子にリチウムイオンが配位した状態で、リチウムイオンが均一に分散した粘着層を形成する。そして、粘着層中においては、リチウムイオンは、エーテル酸素の分子運動によって移動し易い状態になっている。これに外部より電場が印加されると、粘着層中において、リチウムイオンが相応する極に向って移動（イオン輸送）してイオン伝導性を発現する。 As the salt, bis (trifluoromethanesulfonyl) imide lithium is used and dissolved in a polyether ester plasticizer composed of diethylene glycol and adipic acid, as shown in FIG. Ions are coordinated. When the adhesive layer is formed, an adhesive layer in which lithium ions are uniformly dispersed is formed in a state where lithium ions are coordinated to ether oxygen atoms. In the adhesive layer, lithium ions are easily moved by the molecular motion of ether oxygen. When an electric field is applied to this from the outside, lithium ions move (ion transport) toward the corresponding poles in the adhesive layer to develop ionic conductivity.
また、上記フルオロ基及びスルホニル基を有する陰イオンを備えた塩を溶解した媒体である、ジエチレングリコールとアジピン酸とを重合してなるポリエーテルエステル系可塑剤は、その可塑性の発現により、粘着性樹脂にさらなる粘着性を付与するのである。 In addition, a polyether ester plasticizer obtained by polymerizing diethylene glycol and adipic acid, which is a medium in which a salt having an anion having a fluoro group and a sulfonyl group is dissolved, has an adhesive resin due to its plastic expression. It gives further tackiness.
本発明の制電性粘着剤組成物は、例えば、以下のようにして製造される。先ず、ポリエーテル基を主鎖中に含むポリエーテルエステル系可塑剤中に、フルオロ基およびスルホニル基を有する陰イオンを備えた塩を溶解してなる塩溶液を準備する。ポリエーテル基を主鎖中に含むポリエーテルエステル系可塑剤は、フルオロ基およびスルホニル基を有する陰イオンを備えた塩を、発熱しながら、速やかに溶解する。上記塩溶液と粘着性樹脂とを配合し、混練し、制電性粘着剤組成物を形成する。制電性粘着剤組成物を製造するためには、両成分の所定の量を公知の方法を用いて混合すればよい。例えば、ヘンシェルミキサ−、リボンブレンダ−、ス−パ−ミキサ−、タンブラ−などでドライブレンドを行うこともできる。また、単軸または二軸押出機、バンバリ−ミキサ−、プラストミル、コニ−ダ−、ロ−ルなどで溶融混合をおこなってもよい。必要に応じて、窒素などの不活性ガス雰囲気下で行うこともできる。 The antistatic pressure-sensitive adhesive composition of the present invention is produced, for example, as follows. First, a salt solution is prepared by dissolving a salt having an anion having a fluoro group and a sulfonyl group in a polyether ester plasticizer containing a polyether group in the main chain. The polyether ester plasticizer containing a polyether group in the main chain quickly dissolves a salt having an anion having a fluoro group and a sulfonyl group while generating heat. The salt solution and the adhesive resin are blended and kneaded to form an antistatic adhesive composition. In order to produce the antistatic pressure-sensitive adhesive composition, predetermined amounts of both components may be mixed using a known method. For example, dry blending can be performed using a Henschel mixer, a ribbon blender, a super mixer, a tumbler, or the like. Further, melt mixing may be performed with a single-screw or twin-screw extruder, a Banbury mixer, a plast mill, a kneader, a roll, or the like. As needed, it can also carry out in inert gas atmosphere, such as nitrogen.
以下、実施例について説明する。
［参考例１］
Examples will be described below.
[ Reference Example 1]
[アクリル系共重合体Ａ]
冷却管、撹拝機、温度計、滴下漏斗を備えた反応容器に、ｎ−ブチルアクリレート１０部、２−エチルヘキシルアクリレート８８部、４−ヒドロキシブチルアクリレート２部、アクリル酸０．１部と重合開始剤として２，２'一アゾビスイソブチルニトリル０．２部とを酢酸エチル１００部に溶解し、窒素置換後、８０℃で２時間重合して、重合平均分子量６０万のアクリル系共重合体Ａの溶液を得た。アクリル系共重合体Ａの計算Ｔgは−６８℃であった。当該溶液に、酢酸エチルを加えて均一に混合して固形分４０％の粘着剤主剤を得た。
[Acrylic copolymer A]
Polymerization started with 10 parts of n-butyl acrylate, 88 parts of 2-ethylhexyl acrylate, 2 parts of 4-hydroxybutyl acrylate and 0.1 part of acrylic acid in a reaction vessel equipped with a condenser, a stirrer, a thermometer and a dropping funnel Acrylic copolymer A having a polymerization average molecular weight of 600,000 is obtained by dissolving 0.2 part of 2,2′-monoazobisisobutylnitrile as an agent in 100 parts of ethyl acetate, and substituting with nitrogen, followed by polymerization at 80 ° C. for 2 hours. Solution was obtained. The calculation Tg of the acrylic copolymer A was -68 ° C. Ethyl acetate was added to the solution and mixed uniformly to obtain a pressure-sensitive adhesive main agent having a solid content of 40%.
[アクリル系粘着剤組成物Ａ]
上記の粘着主剤に、アクリル系共重合体Ａ１００部に対して、ポリエーテルエステル系可塑剤(モノサイザー（登録商標）Ｗ−２６２、分子量５５６、粘度３０ｍＰａ・ｓ、２５℃、ＤＩＣ社製、式（２）に示す構造式を有する)に、ビス(トリフルオロメタンスルホニル)イミドリチウムを５０質量部溶解した組成物溶液(サンコノール（登録商標）ＡＤ−２６００−５０Ｒ，三光化学工業製)１０部配合し、イソシアネート系架橋剤(コロネート（登録商標）ＨＸ、日本ポリウレタンエ業社製)を１．５部、およびキレート系架橋剤(硬化剤Ｍ−５Ａ，綜研化学社製)を１．０部それぞれ添加し、１５分間撹拌してアクリル系粘着剤組成物を得た。
[Acrylic adhesive composition A]
The above adhesive base material, the acrylic copolymer A100 parts, polyether ester-based plasticizer (Monocizer (registered trademark) W-262, molecular weight 556, viscosity 30 mPa · s, 25 ° C., DIC Corporation, formula 10 parts of a composition solution (Sanconol (registered trademark) AD-2600-50R, manufactured by Sanko Chemical Co., Ltd.) in which 50 parts by mass of bis (trifluoromethanesulfonyl) imide lithium is dissolved in (having the structural formula shown in (2)) , 1.5 parts of isocyanate crosslinking agent (Coronate (registered trademark) HX, manufactured by Nippon Polyurethane Industry Co., Ltd.) and 1.0 part of chelating crosslinking agent (curing agent M-5A, manufactured by Soken Chemical Co., Ltd.) And stirred for 15 minutes to obtain an acrylic pressure-sensitive adhesive composition.
[保護フィルム]
上記のアクリル系粘着剤組成物Ａをシリコーン系剥離剤が塗布された厚さ５０μmの二軸延伸ポリエステルフィルムセパレータ(ＳＰ−ＰＥＴ−０１−ＢＵ，東セロ社製)に乾燥時の厚みが２０μｍになるように塗工し、乾燥した。さらに、厚さ５０μｍの透明な二軸延伸ポリエステルフィルム(Ｔ１００Ｇ，三菱樹脂社製)を上記粘着剤表面に貼り合わせて、透明性の優れた保護フィルムを作成した。該保護フィルムの表面抵抗率を測定した結果、４×１０８Ω／ｓｑであった。このフィルムを湿度７０％、温度８０℃の条件下に１週間放置後、表面抵抗率を測定した結果、５×１０８Ω／ｓｑであった。また、この保護フィルムの剥離帯電圧(剥離角度１５０°、剥離速度１０ｍ／分、春日電機社製ＫＳＤ−０１０３使用)を測定(２３℃、５００％ＲＨ)した。０．０ｋｖであった。
[Protective film]
When the above-mentioned acrylic pressure-sensitive adhesive composition A is dried on a 50 μm-thick biaxially stretched polyester film separator (SP-PET-01-BU, manufactured by Tosero) with a silicone release agent applied, the thickness when dried becomes 20 μm. And then dried. Further, a transparent biaxially stretched polyester film (T100G, manufactured by Mitsubishi Plastics Co., Ltd.) having a thickness of 50 μm was bonded to the pressure-sensitive adhesive surface to prepare a protective film having excellent transparency. The surface resistivity of the protective film was measured and found to be 4 × 10 8 Ω / sq. This film was allowed to stand for 1 week under the conditions of 70% humidity and 80 ° C., and the surface resistivity was measured. As a result, it was 5 × 10 8 Ω / sq. Moreover, the peeling voltage (peeling angle 150 °, peeling speed 10 m / min, using KSD-0103 manufactured by Kasuga Denki Co., Ltd.) of this protective film was measured (23 ° C., 500% RH). It was 0.0 kv.
この保護粘着フィルムを４０℃、６０％ＲＨ環境下で、２日間エージングした後に、接着力(幅２５ｍｍ×長さ８０ｍｍ、剥離速度３００ｍｍ／分、方向１８０°)を測定した。接着力は、０．０３Ｎ／２５ｍｍであった。また、幅２５ｍｍ、長さ８０ｍｍのＰＭＭＡ板に、ＪＩＳ Ｚ０２３７(２０００)に規定された貼付方法で貼付した後、湿熱条件下(６０℃、９０％ＲＨ)で２週間放置後、剥離試験を行った。剥離強さは、０．０２Ｎ／２５ｍｍであった。
［実施例１］
This protective adhesive film was aged for 2 days in an environment of 40 ° C. and 60% RH, and then the adhesive strength (width 25 mm × length 80 mm, peeling speed 300 mm / min, direction 180 °) was measured. The adhesive force was 0.03 N / 25 mm. In addition, after affixing to a PMMA plate with a width of 25 mm and a length of 80 mm by the application method specified in JIS Z0237 (2000), the sample was left for 2 weeks under wet heat conditions (60 ° C., 90% RH), and then a peel test was performed. It was. The peel strength was 0.02 N / 25 mm.
[Example 1 ]
[アクリル系粘着剤組成物Ｂ]
参考例１の粘着主剤に、アクリル系共重合体Ａ１００部に対して、ポリエーテルエステル系可塑剤として、式（２）に示すモノサイザー（登録商標）Ｗ−２６２と式（１）に示すポリサイザーＷ−２３０−Ｈ(分子量約１０００、粘度２２０ｍＰａ・ｓ、２５℃、ＤＩＣ社製)との１：１混合物に、ビス(トリフルオロメタンスルホニル)イミドリチウムを２０質量部溶解した組成物(サンコノール（登録商標）ＡＤ−２６２３−２０Ｒ，三光化学工業株式会社製)１５部と、イソシアナート系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０．６質量部を添加し、１５分間撹梓して、参考例１と同様な方法でアクリル系粘着剤組成物Ｂを得た。
[Acrylic adhesive composition B]
Monocizer (registered trademark) W-262 shown in Formula (2) and Polycizer shown in Formula (1) as a polyetherester plasticizer with respect to 100 parts of acrylic copolymer A as the adhesive main agent of Reference Example 1 A composition obtained by dissolving 20 parts by mass of bis (trifluoromethanesulfonyl) imidolithium in a 1: 1 mixture with W-230-H (molecular weight: about 1000, viscosity: 220 mPa · s, 25 ° C., manufactured by DIC) (Sanconol (registered) TM) AD-2623-20R, three and photochemical industry Co., Ltd.) 15 parts, was added tolylene diisocyanate adduct 0.6 parts by weight of isocyanate-based trimethylol propane, and撹梓15 minutes, reference example 1 Acrylic pressure-sensitive adhesive composition B was obtained in the same manner as above.
[粘着シート]
上記製造したアクリル系粘着剤組成物Ｂを、剥離紙にコーティングして乾燥した後、厚さ１５μｍの均一な粘着層を有する粘着シートを得た。該粘着層を膜厚１８５μｍのヨード系偏光板に粘着加工した。該粘着層の表面抵抗率を測定した結果、８×１０8Ω／ｓｑであった。また、粘着シートの剥離帯電圧(剥離角度１５０°、剥離速度１０ｍ／分、春日電機社製ＫＳＤ−０１０３使用)を測定した結果、０．０ｋｖで、１８０°、剥離粘着力は、３．２Ｎ／２５ｍｍであった。
［参考例２］
[Adhesive sheet]
The prepared acrylic pressure-sensitive adhesive composition B was coated on a release paper and dried, and then a pressure-sensitive adhesive sheet having a uniform pressure-sensitive adhesive layer having a thickness of 15 μm was obtained. The pressure-sensitive adhesive layer was pressure-bonded to an iodine-type polarizing plate having a film thickness of 185 μm. As a result of measuring the surface resistivity of the adhesive layer, it was 8 × 10 8 Ω / sq. Moreover, as a result of measuring the peeling voltage of the adhesive sheet (peeling angle 150 °, peeling speed 10 m / min, using KSD-0103 manufactured by Kasuga Denki Co., Ltd.), 0.0 kv, 180 °, and peel adhesive strength is 3.2 N. / 25 mm.
[ Reference Example 2 ]
参考例１のアクリル系共重合体Ａ１００部に対して、ポリエーテルエステル系可塑剤(モノサイザー（登録商標）Ｗ−２６２)に、トリフルオロメタンスルホン酸リチウムを７０質量部溶解した組成物を５部配合した以外は、参考例１と同様にして、アクリル系粘着剤組成物を調製し、次いで、保護粘着フィルムを得た。該保護フィルムの表面抵抗率は、２×１０10Ω／ｓｑであった。また、この保護フィルムの剥離帯電圧は、０．０ｋｖであった。
［実施例２］
5 parts of a composition obtained by dissolving 70 parts by mass of lithium trifluoromethanesulfonate in a polyether ester plasticizer (Monocizer (registered trademark) W-262) with respect to 100 parts of acrylic copolymer A of Reference Example 1 An acrylic pressure-sensitive adhesive composition was prepared in the same manner as in Reference Example 1 except that it was blended, and then a protective pressure-sensitive adhesive film was obtained. The surface resistivity of the protective film was 2 × 10 10 Ω / sq. Moreover, the peeling voltage of this protective film was 0.0 kv.
[ Example 2 ]
参考例１のアクリル系共重合体Ａ１００部に対して、ポリエーテルエステル系化合物(モノサイザー（登録商標）Ｗ−２６２とポリサイザー（登録商標）Ｗ−２３０−Ｈとの１：１混合物)に、ビス(トリフルオロメタンスルポニル)イミドリチウムを２０質量部溶解した組成物を１０部配合した以外は、実施例１と同様にして、アクリル系粘着剤組成物を調製した。次いで、剥離紙にコーテリングして、乾燥した後、厚さ１０μｍの粘着シートを得た。該粘着層を、先ず、ヨード系偏光板に粘着加工した後、２枚のトリアセチルセルロース(ＴＡＣ)フィルムで挟み接着した。この３層構造のフィルムの体積抵抗率は、１×１０10Ω・cmであった。
For 100 parts of acrylic copolymer A of Reference Example 1, a polyetherester compound (a 1: 1 mixture of Monosizer (registered trademark) W-262 and Polysizer (registered trademark) W-230-H), An acrylic pressure-sensitive adhesive composition was prepared in the same manner as in Example 1 except that 10 parts of a composition in which 20 parts by mass of bis (trifluoromethanesulfonyl) imide lithium was dissolved was blended. Subsequently, after coating with release paper and drying, an adhesive sheet having a thickness of 10 μm was obtained. The pressure-sensitive adhesive layer was first subjected to pressure-sensitive adhesive processing on an iodine-type polarizing plate, and then sandwiched between two triacetyl cellulose (TAC) films and bonded. The volume resistivity of this three-layer film was 1 × 10 10 Ω · cm.
上記実施例ではポリエーテル基としてポリエチレングリコールを例示したが、この発明はこれに限られるものでなく、ポリプロピレングリコールを用いても、相当の効果を奏する。 In the above embodiment, polyethylene glycol is exemplified as the polyether group. However, the present invention is not limited to this, and even if polypropylene glycol is used, a considerable effect can be obtained.
また、本発明において用いられるフルオロ基及びスルホニル基を備える陰イオンを有する塩としては、上述したもの以外にも、たとえば、リチウムビス（フルオロスルホニル）イミド、ＬｉＮ（Ｃ２Ｆ５ＳＯ２）２、ＬｉＮ（Ｃ４Ｆ９ＳＯ２）（ＣＦ３ＳＯ２）、ＬｉＮ（Ｃ８Ｆ１７ＳＯ２）（ＣＦ３ＳＯ２）、ＬｉＮ（ＣＦ３ＣＨ２ＯＳＯ２）２、ＬｉＮ（ＣＦ３ＣＦ２ＣＨ２ＯＳＯ２）２、ＬｉＮ（ＨＣＦ２ＣＦ２ＣＨ２ＯＳＯ２）２、ＬｉＮ（（ＣＦ３）２ＣＨＯＳＯ２）２、トリス(フルオロアルキルスルホニル)メチドリチウム Ｌｉ(ＣＦ３ＳＯ２)３Ｃなども使用できる。 In addition to the above-described salts having an anion having a fluoro group and a sulfonyl group used in the present invention, for example, lithium bis (fluorosulfonyl) imide, LiN (C 2 F 5 SO 2 ) 2 , LiN (C 4 F 9 SO 2 ) (CF 3 SO 2), LiN (C 8 F 17 SO 2) (CF 3 SO 2), LiN (CF 3 CH 2 OSO 2) 2, LiN (CF 3 CF 2 CH 2 OSO 2 ) 2, LiN (HCF 2 CF 2 CH 2 OSO 2 ) 2 , LiN ((CF 3 ) 2 CHOSO 2 ) 2 , tris (fluoroalkylsulfonyl) methidolithium Li (CF 3 SO 2 ) 3 C, etc. are also used. it can.
本発明の制電性粘着剤組成物は、基材と粘着剤層とを有する保護粘着フィルムや、偏光フィルタと位相差フィルムとの貼り合わせ、偏光フィルムと表面保護板との貼り合わせ、位相差フィルムと液晶セル（液晶を基板間に封入した部品）との貼り合わせなどに使用できる。また、本発明に係る制電性粘着剤組成物を用いて粘着加工を施した偏光フィルムは、携帯型ワープロやパソコンのディスプレイ、自動車の表示パネル、腕時計や電卓の表示部、さらには携帯型テレビまで数多くの液晶ディスプレイに利用することができる。 The antistatic pressure-sensitive adhesive composition of the present invention includes a protective adhesive film having a base material and a pressure-sensitive adhesive layer, a lamination of a polarizing filter and a retardation film, a lamination of a polarizing film and a surface protective plate, and a retardation. It can be used for bonding a film and a liquid crystal cell (parts in which liquid crystal is sealed between substrates). In addition, a polarizing film subjected to adhesive processing using the antistatic adhesive composition according to the present invention is a portable word processor, a display of a personal computer, a display panel of an automobile, a display part of a wristwatch or a calculator, and further a portable television. Can be used for many liquid crystal displays.
今回開示された実施例はすべての点で例示であって制限的なものではないと考えられるべきである。本発明の範囲は上記した説明ではなくて特許請求の範囲によって示され、特許請求の範囲と均等の意味および範囲内でのすべての変更が含まれることが意図される。 It should be understood that the embodiments disclosed herein are illustrative and non-restrictive in every respect. The scope of the present invention is defined by the terms of the claims, rather than the description above, and is intended to include any modifications within the scope and meaning equivalent to the terms of the claims.
本発明によれば、熱安定性に優れ、ブリ-ディング、ブル-ミングおよび移行汚染が発生せず、湿度に依存せずに、速効性に優れ、物性の低下を招かず、かつ、優れた制電性が持続する制電性粘着剤組成物が得られる。保護フィルム、偏光フィルム及び位相差フィルムなどの帯電防止性を持たせた粘着加工に利用できる。 According to the present invention, the thermal stability is excellent, no bleeding, blooming and migration contamination occur, it does not depend on humidity, it has excellent rapidity, no deterioration in physical properties, and excellent An antistatic pressure-sensitive adhesive composition that maintains antistatic properties is obtained. It can be used for adhesive processing with antistatic properties such as protective films, polarizing films and retardation films.
Claims (11)
前記フルオロ基およびスルホニル基を有する陰イオンを備えた塩は、下記式（１）に示すポリエーテル基を主鎖中に含むポリエーテルエステル系可塑剤に溶解された状態で分散されていることを特徴とする制電性粘着剤組成物。
The salt having an anion having a fluoro group and a sulfonyl group is dispersed in a state dissolved in a polyether ester plasticizer containing a polyether group represented by the following formula (1) in the main chain. An antistatic pressure-sensitive adhesive composition.
前記粘着剤層が、請求項１〜８のいずれか１項に記載の制電性粘着剤組成物から形成されていることを特徴とする保護粘着フィルム。 A protective adhesive film having a substrate and an adhesive layer,
The said adhesive layer is formed from the antistatic adhesive composition of any one of Claims 1-8, The protective adhesive film characterized by the above-mentioned.
前記粘着剤層が、請求項１〜８のいずれか１項に記載の制電性粘着剤組成物から形成 されていることを特徴とする偏光フィルム。 A polarizing film having a substrate and an adhesive layer,
Polarizing film, wherein the pressure-sensitive adhesive layer, characterized in that it is formed from an antistatic pressure-sensitive adhesive composition according to any one of claims 1-8.
前記粘着剤層が、請求項１〜８のいずれか１項に記載の制電性粘着剤組成物から形成さ れていることを特徴とする位相差フィルム。 A retardation film having a base material and an adhesive layer,
The retardation film the adhesive layer, characterized in that it is formed from an antistatic pressure-sensitive adhesive composition according to any one of claims 1-8.
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| JP6433143B2 (en) * | 2014-04-16 | 2018-12-05 | 日東電工株式会社 | Adhesive sheet and optical member |
| JP6905502B2 (en) * | 2014-04-16 | 2021-07-21 | 日東電工株式会社 | Adhesive sheet and optical member |
| WO2015194523A1 (en) * | 2014-06-18 | 2015-12-23 | 住友化学株式会社 | Polarizer, polarizer plate with adhesive, and image display device |
| CN106795416A (en) * | 2014-06-18 | 2017-05-31 | 王子控股株式会社 | Polarizer adhesive composition and polarizer bonding sheet |
| CN106795413A (en) * | 2014-06-18 | 2017-05-31 | 王子控股株式会社 | Polarizer adhesive composition and polarizer bonding sheet |
| JP2016121306A (en) * | 2014-12-25 | 2016-07-07 | 日東電工株式会社 | Adhesive composition, adhesive sheet and optical member |
| JP2016121305A (en) * | 2014-12-25 | 2016-07-07 | 日東電工株式会社 | Adhesive composition, adhesive sheet and optical member |
| KR101851430B1 (en) | 2015-03-04 | 2018-04-24 | 동우 화인켐 주식회사 | Retardation Film and Polarizing Plate Using the Same |
| JP6675242B2 (en) * | 2016-03-18 | 2020-04-01 | 日本カーバイド工業株式会社 | Pressure-sensitive adhesive composition and polarizing plate with pressure-sensitive adhesive layer |
| JP6677673B2 (en) | 2017-05-15 | 2020-04-08 | 藤森工業株式会社 | Pressure-sensitive adhesive composition and surface protective film |
| JP6799517B2 (en) | 2017-09-28 | 2020-12-16 | 藤森工業株式会社 | Adhesive composition and surface protective film |
| JP2019143007A (en) * | 2018-02-19 | 2019-08-29 | 王子ホールディングス株式会社 | Pressure sensitive adhesive composition, adhesive sheet, and layered body |
| JP7255990B2 (en) | 2018-09-27 | 2023-04-11 | 藤森工業株式会社 | surface protection film |
| JP7193286B2 (en) | 2018-09-27 | 2022-12-20 | 藤森工業株式会社 | surface protection film |
| JP7207961B2 (en) | 2018-11-12 | 2023-01-18 | 藤森工業株式会社 | Adhesive composition, and adhesive film and surface protective film using the same |
| JP7244369B2 (en) | 2019-06-25 | 2023-03-22 | 藤森工業株式会社 | Method for producing antistatic surface protective film, antistatic surface protective film |
| KR20230004816A (en) * | 2020-07-15 | 2023-01-06 | 케이와 인코포레이티드 | protective sheet and laminate |
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